阅读说明：本技术 化妆品配合剂、化妆品及其制造方法 (Cosmetic compounding agent, cosmetic and method for producing same ) 是由 金子恒太郎 矢下亚纪良 河合功治 川上隼人 伊庭缓昌 于 2020-02-13 设计创作，主要内容包括：提供在应用于毛发或皮肤时赋予化妆品包括保水保湿性的优异性质的新型化妆品配合剂、使用该化妆品配合剂的化妆品及其制造方法。本发明的化妆品配合剂含有在阳离子和阴离子的至少任一者中具有氢键性官能团的有机铵盐。在优选方案中,所述阳离子是铵阳离子,由下式(I)表示,式(I)中,R～1分别独立地表示具有1个以上的羟基并且烷基部位为碳数1～10的直链状或支链状且该烷基部位含有或不含有氧原子的羟基烷基等,R～2分别独立地为氢原子或碳数1～18的直链或支链的烷基,n表示0～4的整数。N～+[R～1]-n[R～2]-(4-n) (I)。(Provided are a novel cosmetic compounding agent which imparts excellent properties including water retention and moisture retention to a cosmetic when applied to hair or skin, a cosmetic using the cosmetic compounding agent, and a method for producing the cosmetic. The cosmetic compounding agent of the present invention contains an organic ammonium salt having a hydrogen-bonding functional group in at least either one of a cation and an anion. In a preferred embodiment, the cation is an ammonium cation represented by the following formula (I) wherein R is 1 Each independently represents a straight-chain or branched-chain hydroxyalkyl group having 1 or more hydroxyl groups and having 1 to 10 carbon atoms in the alkyl moiety, with or without an oxygen atom in the alkyl moiety, or the like, R 2 Each independently represents a hydrogen atom or a linear or branched alkyl group having 1 to 18 carbon atoms, and n represents an integer of 0 to 4. N is a radical of + [R 1 ] n [R 2 ] 4‑n (I)。)

1. A cosmetic compounding agent comprising an organic ammonium salt having a hydrogen-bonding functional group in at least either one of a cation and an anion.

2. The cosmetic formulation of claim 1, wherein the cation is an ammonium cation.

3. The cosmetic compounding agent according to claim 2, wherein the ammonium cation is represented by the following formula (I),

N⁺[R¹]_n[R²]_4-n (I)

in the formula (I), R¹Each independently represents a straight or branched chain having 1 or more hydroxyl groups and having 1 to 10 carbon atoms in the alkyl moiety with or without the alkyl moietyA hydroxyalkyl group having an oxygen atom, a carboxyalkyl group having 1 or more carboxyl groups and having an alkyl moiety of 1 to 10 carbon atoms in a straight chain or branched chain state and containing or not containing an oxygen atom in the alkyl moiety, or a hydroxycarboxyalkyl group having 1 or more hydroxyl groups and carboxyl groups respectively and having an alkyl moiety of 1 to 10 carbon atoms in a straight chain or branched chain state and containing or not containing an oxygen atom in the alkyl moiety, R²Each independently represents a hydrogen atom or a linear or branched alkyl group having 1 to 18 carbon atoms, and n represents an integer of 0 to 4.

4. The cosmetic compounding agent according to claim 3, wherein n is an integer of 1 to 4.

5. The cosmetic formulation of claim 3 or 4, wherein R²Is a hydrogen atom.

6. The cosmetic formulation of claim 4, wherein R¹Is a straight-chain or branched monohydroxyalkyl group or a monocarboxyalkyl group having 1 to 10 carbon atoms in the alkyl moiety.

7. The cosmetic formulation of claim 6, wherein R²Is a hydrogen atom.

8. The cosmetic formulation of claim 4, wherein R²Is a linear or branched alkyl group having 1 to 18 carbon atoms.

9. The cosmetic formulation of claim 4, wherein R¹At least one of the groups is a straight-chain or branched polyhydroxyalkyl group having 2 or more hydroxyl groups and having 1 to 10 carbon atoms in the alkyl moiety.

10. The cosmetic formulation of claim 9, wherein R²Is a hydrogen atom.

11. The cosmetic ingredient according to any one of claims 1 to 10, wherein the anion is a carboxylic acid-based anion.

12. The cosmetic formulation of claim 11, wherein said anion has a hydrogen-bonding functional group.

13. The cosmetic compounding agent according to claim 12, wherein the hydrogen-bonding functional group is any one of a hydroxyl group, a carboxyl group and a carboxylate group.

14. The cosmetic ingredient according to any one of claims 1 to 13, wherein the anhydrate and hydrate of the organic ammonium salt are liquid at 25 ℃.

15. The cosmetic compounding agent according to any one of claims 1 to 14, wherein the base and the acid are each compounded to form the organic ammonium salt.

16. The cosmetic formulation according to claim 1, which is a hair treatment agent.

17. The cosmetic formulation of claim 16, wherein the cation is an ammonium cation.

18. The cosmetic formulation of claim 17, wherein said ammonium cation is represented by the following formula (I),

N⁺[R¹]_n[R²]_4-n (I)

in the formula (I), R¹Independently represents a hydroxyalkyl group having 1 or more hydroxyl groups, having an alkyl moiety of 1 to 10 carbon atoms and being linear or branched, wherein the alkyl moiety contains or does not contain an oxygen atom, a carboxyalkyl group having 1 or more carboxyl groups, having an alkyl moiety of 1 to 10 carbon atoms and being linear or branched, wherein the alkyl moiety contains or does not contain an oxygen atom, or a hydroxyl group having 1 or more hydroxyl groups and carboxyl groups, wherein the alkyl moiety is linear or branched, wherein the alkyl moiety contains or does not contain an oxygen atomCarboxyalkyl, R²Each independently represents a hydrogen atom or a linear or branched alkyl group having 1 to 18 carbon atoms, and n represents an integer of 0 to 4.

19. The cosmetic formulation of claim 18, wherein n is an integer of 1 to 4.

20. The cosmetic formulation of claim 18 or 19, wherein R²Is a hydrogen atom.

21. The cosmetic formulation of claim 19, wherein R¹Is a straight-chain or branched monohydroxyalkyl group or a monocarboxyalkyl group having 1 to 10 carbon atoms in the alkyl moiety.

22. The cosmetic formulation of claim 21, wherein R²Is a hydrogen atom.

23. The cosmetic formulation of claim 19, wherein R²Is a linear or branched alkyl group having 1 to 18 carbon atoms.

24. The cosmetic formulation of claim 19, wherein R¹At least one of the groups is a straight-chain or branched polyhydroxyalkyl group having 2 or more hydroxyl groups and having 1 to 10 carbon atoms in the alkyl moiety.

25. The cosmetic formulation of claim 24, wherein R²Is a hydrogen atom.

26. The cosmetic ingredient according to any one of claims 16 to 25, wherein the anion is a carboxylic acid-based anion.

27. The cosmetic formulation of any one of claims 26, wherein a hydrogen-bonding functional group is present in the anion.

28. The cosmetic compounding agent according to claim 27, wherein the hydrogen-bonding functional group is any one of a hydroxyl group, a carboxyl group and a carboxylate group.

29. The cosmetic ingredient according to any one of claims 16 to 28, wherein the anhydrate or hydrate of the organic ammonium salt is liquid at 25 ℃.

30. The cosmetic compounding agent according to any one of claims 16 to 29, wherein the base and the acid are each compounded to form the organic ammonium salt.

31. The cosmetic formulation of claim 1, wherein it is a skin care agent.

32. The cosmetic formulation of claim 31, wherein the cation is an ammonium cation.

33. The cosmetic formulation of claim 32, wherein said ammonium cation is represented by the following formula (I),

N⁺[R¹]_n[R²]_4-n (I)

in the formula (I), R¹Each independently represents a hydroxyalkyl group having 1 or more hydroxyl groups, having an alkyl moiety of 1 to 10 carbon atoms in a straight or branched chain state, and containing or not containing an oxygen atom in the alkyl moiety, a carboxyalkyl group having 1 or more carboxyl groups, having an alkyl moiety of 1 to 10 carbon atoms in a straight or branched chain state, and containing or not containing an oxygen atom in the alkyl moiety, or a hydroxycarboxyalkyl group having 1 or more hydroxyl groups and 1 to 10 carbon atoms in a straight or branched chain state, and containing or not containing an oxygen atom in the alkyl moiety, R²Each independently represents a hydrogen atom or a linear or branched alkyl group having 1 to 18 carbon atoms, and n represents an integer of 0 to 4.

34. The cosmetic ingredient according to claim 33, wherein n is an integer of 1 to 4.

35. The cosmetic formulation of claim 33 or 34, wherein R²Is a hydrogen atom.

36. The cosmetic formulation of claim 34, wherein R¹Is a straight-chain or branched monohydroxyalkyl group or a monocarboxyalkyl group having 1 to 10 carbon atoms in the alkyl moiety.

37. The cosmetic formulation of claim 36, wherein R²Is a hydrogen atom.

38. The cosmetic formulation of claim 34, wherein R²Is a linear or branched alkyl group having 1 to 18 carbon atoms.

39. The cosmetic formulation of claim 34, wherein R¹At least one of the groups is a straight-chain or branched polyhydroxyalkyl group having 2 or more hydroxyl groups and having 1 to 10 carbon atoms in the alkyl moiety.

40. The cosmetic formulation of claim 39, wherein R²Is a hydrogen atom.

41. The cosmetic ingredient according to any one of claims 31 to 40, wherein the anion is a carboxylic acid-based anion.

42. The cosmetic formulation of claim 41, wherein said anion has a hydrogen-bonding functional group.

43. The cosmetic compounding agent according to claim 42, wherein the hydrogen-bonding functional group is any one of a hydroxyl group, a carboxyl group and a carboxylate group.

44. The cosmetic ingredient according to any one of claims 31 to 43, wherein the anhydrate or hydrate of the organic ammonium salt is liquid at 25 ℃.

45. The cosmetic compounding agent according to any one of claims 31 to 44, wherein the base and the acid are each compounded to form the organic ammonium salt.

46. A cosmetic comprising the cosmetic compounding agent according to any one of claims 1 to 45.

47. The cosmetic according to claim 46, which is a hair treatment composition.

48. The cosmetic of claim 46, wherein it is a skin care composition.

49. A cosmetic composition comprising, as raw materials for a cosmetic composition, an ammonium cation-forming base and an anion-forming acid, wherein the base and the acid form an organic ammonium salt comprising an ammonium cation represented by the following formula (I) and an anion,

N⁺[R¹]_n[R²]_4-n (I)

in the formula (I), R¹Each independently represents a hydroxyalkyl group having 1 or more hydroxyl groups, having an alkyl moiety of 1 to 10 carbon atoms in a straight or branched chain state, and containing or not containing an oxygen atom in the alkyl moiety, a carboxyalkyl group having 1 or more carboxyl groups, having an alkyl moiety of 1 to 10 carbon atoms in a straight or branched chain state, and containing or not containing an oxygen atom in the alkyl moiety, or a hydroxycarboxyalkyl group having 1 or more hydroxyl groups and 1 to 10 carbon atoms in a straight or branched chain state, and containing or not containing an oxygen atom in the alkyl moiety, R²Each independently represents a hydrogen atom or a linear or branched alkyl group having 1 to 18 carbon atoms, and n represents an integer of 0 to 4.

50. The cosmetic according to claim 49, wherein n is an integer of 1 to 4.

51. The cosmetic of claim 50, wherein R²Is a hydrogen atom.

52. The cosmetic of claim 50, wherein R¹Is a straight-chain or branched monohydroxyalkyl group or a monocarboxyalkyl group having 1 to 10 carbon atoms in the alkyl moiety.

53. The cosmetic of claim 52, wherein R²Is a hydrogen atom.

54. The cosmetic of claim 50, wherein R²Is a linear or branched alkyl group having 1 to 18 carbon atoms.

55. The cosmetic of claim 50, wherein R¹At least one of the groups is a straight-chain or branched polyhydroxyalkyl group having 2 or more hydroxyl groups and having 1 to 10 carbon atoms in the alkyl moiety.

56. The cosmetic of claim 55 wherein R²Is a hydrogen atom.

57. The cosmetic according to any one of claims 49 to 56, wherein the anion is a carboxylic acid-based anion.

58. The cosmetic of claim 57, wherein a hydrogen-bonding functional group is present in the anion.

59. The cosmetic according to claim 58, wherein the hydrogen-bonding functional group is any one of a hydroxyl group, a carboxyl group and a carboxylate group.

60. The cosmetic according to any one of claims 49 to 59, wherein the anhydrate or hydrate of the organic ammonium salt is liquid at 25 ℃.

61. The cosmetic according to any one of claims 49 to 60, wherein the cosmetic is a hair treatment composition.

62. The cosmetic of any one of claims 49 to 60, wherein the cosmetic is a skin care composition.

63. A method for producing a cosmetic, comprising the step of blending the cosmetic compounding agent according to any one of claims 1 to 45.

64. A method for producing a cosmetic composition, comprising a step of mixing a base which forms an ammonium cation with an acid which forms an anion, wherein the base and the acid form an organic ammonium salt comprising the ammonium cation represented by the following formula (I) and the anion,

N⁺[R¹]_n[R²]_4-n (I)

in the formula (I), R¹Each independently represents a hydroxyalkyl group having 1 or more hydroxyl groups, having an alkyl moiety of 1 to 10 carbon atoms in a straight or branched chain state, and containing or not containing an oxygen atom in the alkyl moiety, a carboxyalkyl group having 1 or more carboxyl groups, having an alkyl moiety of 1 to 10 carbon atoms in a straight or branched chain state, and containing or not containing an oxygen atom in the alkyl moiety, or a hydroxycarboxyalkyl group having 1 or more hydroxyl groups and 1 to 10 carbon atoms in a straight or branched chain state, and containing or not containing an oxygen atom in the alkyl moiety, R²Each independently represents a hydrogen atom or a linear or branched alkyl group having 1 to 18 carbon atoms, and n represents an integer of 0 to 4.

65. The method for producing a cosmetic according to claim 64, wherein the base and the acid are mixed to prepare a cosmetic compounding agent containing the organic ammonium salt, and then the cosmetic compounding agent is compounded as a raw material for a cosmetic.

66. The method for producing a cosmetic according to claim 64, wherein the base and the acid are each blended as a raw material of a cosmetic.

67. The method for producing a cosmetic according to any one of claims 64 to 66, wherein n is an integer of 1 to 4.

68. The method for producing a cosmetic according to claim 64 to 67, wherein R is²Is a hydrogen atom.

69. The method for producing a cosmetic according to claim 67, wherein R is¹Is a straight-chain or branched monohydroxyalkyl group or a monocarboxyalkyl group having 1 to 10 carbon atoms in the alkyl moiety.

70. The method for producing a cosmetic according to claim 69, wherein R is²Is a hydrogen atom.

71. The method for producing a cosmetic according to claim 67, wherein R is²Is a linear or branched alkyl group having 1 to 18 carbon atoms.

72. The method for producing a cosmetic according to claim 67, wherein R is¹At least one of the groups is a straight-chain or branched polyhydroxyalkyl group having 2 or more hydroxyl groups and having 1 to 10 carbon atoms in the alkyl moiety.

73. The method for producing a cosmetic according to claim 72, wherein R is²Is a hydrogen atom.

74. The method for producing a cosmetic according to any one of claims 64 to 73, wherein the anion is a carboxylic acid anion.

75. The method for producing a cosmetic according to claim 74, wherein the anion has a hydrogen-bonding functional group.

76. The method for producing a cosmetic according to claim 75, wherein the hydrogen-bonding functional group is any one of a hydroxyl group, a carboxyl group and a carboxylate group.

77. The method for producing a cosmetic according to any one of claims 64 to 76, wherein the anhydrate or hydrate of the organic ammonium salt is liquid at 25 ℃.

78. The method for producing a cosmetic according to any one of claims 63 to 77, wherein the cosmetic is a hair treatment composition.

79. The method for producing a cosmetic according to any one of claims 63 to 77, wherein the cosmetic is a skin care composition.

Technical Field

The present invention relates to a cosmetic compounding agent, a cosmetic, and a method for producing the same.

Background

Conventionally, it has been known that a cosmetic used for hair treatment, skin care products, or the like contains a component for the purpose of a water retention and moisture retention effect. However, these components may deteriorate the feeling in use such as stickiness, and a component satisfying water retention and moisture retention and feeling in use is desired.

Air drying, shampoo with high cleaning power, hair drier heat, natural drying after bathing, hair perm, hair damage caused by hair dyeing, etc. When the hair is dry and the moisture is insufficient, the cuticle (cuticle), which is an important tissue for covering the hair surface to prevent the evaporation of the moisture, to make the hair glossy, and to keep the hair healthy, is easily peeled off. If the cuticle is removed, the hair becomes dry, for example, it loses smoothness, and the hair becomes dry, so that the hair is not only poor in softness and finger combing property, but also is easily rough, branched and broken. Therefore, water retention and moisture retention of hair are important in order to prevent problems caused by hair drying and maintain the hair beautiful and healthy.

Conventionally, it has been proposed to blend a polyol as a moisture-retaining component in a hair treatment composition such as a shampoo (see patent documents 1 and 2). However, in the conventional hair treatment compositions, for example, there are cases where the water retention and moisture retention performance is insufficient in a low humidity environment such as drying after shampooing and drying in winter, or there are cases where the compositions are volatile and cannot maintain the water retention and moisture retention effect for a long period of time, and therefore, a novel hair treatment composition capable of improving this point is desired.

Patent document 3 discloses organic ammonium salts such as imidazolium salts, pyrrolidinium salts, piperidinium salts, pyridinium salts, and phosphonium salts. Such organic ammonium salts have a property of retaining water, but have problems in terms of sufficient water-retaining and moisture-retaining effects and safety when applied to hair.

The present applicant has proposed an organic salt (ionic liquid) having a hydrogen bonding functional group in a cation or anion (patent documents 4 and 5), but has not specifically studied the application of the water-retaining and moisture-retaining effect to hair and skin care products.

It is known that skin roughness is mainly caused by a decrease in skin moisture. For example, winter air dryness, skin cleansing, aging, reduction in skin secretions, and the like result in dry skin. When the skin is left in a dry state, the elasticity and luster of the skin are reduced, and a so-called rough skin state is likely to be formed. It is important to prevent the deterioration of the moisture content of the stratum corneum and to maintain normal skin function to prevent skin roughness. In order to maintain the amount of keratinous water, skin care agents for the purpose of imparting moderate moisture to the skin and various moisturizing agents have been known.

Conventionally, it has been proposed to blend a polyhydric alcohol as a moisture-retaining component in a skin care agent (see patent document 1). However, conventional skin care agents have insufficient water retention and moisture retention performance in a low humidity environment such as when dried in winter, or have volatility and cannot maintain the water retention and moisture retention effect for a long period of time, and a novel skin care agent capable of improving this is desired.

Patent document 3 discloses organic ammonium salts such as imidazolium salts, pyrrolidinium salts, piperidinium salts, pyridinium salts, and phosphonium salts. Such organic ammonium salts have a property of retaining water, but have problems in terms of sufficient water-retaining and moisture-retaining effects and safety when used for skin care products.

The present applicant has proposed an organic salt (ionic liquid) having a hydrogen bonding functional group in a cation or anion, and a water-retaining humectant (patent documents 4 to 6).

Documents of the prior art

Patent document

Patent document 1: japanese patent laid-open No. 2014-136678.

Patent document 2: japanese patent laid-open publication No. 2013 and 40153.

Patent document 3: japanese patent laid-open No. 2014-151015.

Patent document 4: japanese patent laid-open No. 2014-131974.

Patent document 5: japanese patent laid-open No. 2014-131975.

Patent document 6: japanese patent laid-open publication No. 2019-023185.

Disclosure of Invention

Problems to be solved by the invention

However, although a cosmetic compounding agent which is not volatilized and remains, and has a short-term and long-term water retention and moisture retention property, an affinity for hair, skin, and the like, high safety, and an excellent feeling in use is desired, there is no cosmetic compounding agent which can satisfy all the requirements. In addition, when the active ingredient is dissolved, it is required to exhibit the effect of the active ingredient efficiently, and it is desired to improve the solubility and permeability of the active ingredient.

When the cosmetic compounding agent is a hair treatment agent, a cosmetic compounding agent having good feeling of use and excellent adhesion to proteins contained in hair and thermal stability is desired, and in the case of a skin care agent, a cosmetic compounding agent having good feeling of use and improved affinity to the skin, permeability, and whitening effect is desired.

Conventionally, although it has been known to provide a water-retaining and moisture-retaining ability to a cosmetic compounding agent using a polyhydric alcohol, a cosmetic compounding agent having a higher water-retaining and moisture-retaining ability and the above-described effects, and a composition using the same are desired.

The present invention has been made in view of the above circumstances, and a main object thereof is to provide a novel cosmetic compounding agent which imparts excellent properties including water retention and moisture retention to a cosmetic when applied to hair or skin, a cosmetic using the cosmetic compounding agent, and a method for producing the cosmetic.

In particular, an object of the present invention is to provide a hair treatment agent which, when a cosmetic compounding agent is a hair treatment agent, has high adhesion to hair, excellent water retention and affinity, and good use feeling such as finger combing property, flexibility, touch, elasticity, toughness, thickening, cohesiveness, moist feeling, gloss, smoothness, and non-stickiness, and which is excellent in adhesion to proteins contained in hair, stability, thermal stability, and solubility of active ingredients, and a hair treatment composition using the hair treatment agent.

In particular, when the cosmetic compounding agent is a skin care agent, it is excellent in moisture retention and moisture barrier properties for a short period and a long period of time, and also has good feeling of use such as moisture retention, stickiness, and skin compatibility, excellent affinity and permeability to the skin, and high safety to the skin. The invention further provides a skin care agent having high solubility of active ingredients and excellent whitening effect and antistatic property, and a skin care composition using the skin care agent.

Means for solving the problems

In order to solve the above problems, the cosmetic compounding agent of the present invention is characterized by containing an organic ammonium salt having a hydrogen-bonding functional group in at least either one of a cation and an anion.

In a preferred example, the cation is an ammonium cation.

In a preferred example, the ammonium cation is represented by the following formula (I).

N⁺[R¹]_n[R²]_4-n (I)

In the formula (I), R¹Each independently represents a hydroxyalkyl group having 1 or more hydroxyl groups, having an alkyl moiety of 1 to 10 carbon atoms in a straight or branched chain state, and containing or not containing an oxygen atom in the alkyl moiety, a carboxyalkyl group having 1 or more carboxyl groups, having an alkyl moiety of 1 to 10 carbon atoms in a straight or branched chain state, and containing or not containing an oxygen atom in the alkyl moiety, or a hydroxycarboxyalkyl group having 1 or more hydroxyl groups and 1 to 10 carbon atoms in a straight or branched chain state, and containing or not containing an oxygen atom in the alkyl moiety, R²Each independently represents a hydrogen atom or a linear or branched alkyl group having 1 to 18 carbon atoms, and n represents an integer of 0 to 4.

In a preferred example, the cosmetic compounding agent is a hair treatment agent.

In a preferred embodiment, the cosmetic formulation is a skin care agent.

The cosmetic of the present invention contains the cosmetic compounding agent.

In a preferred example, the cosmetic is a hair treatment composition.

In a preferred example, the cosmetic is a skin care composition.

The method for producing a cosmetic of the present invention comprises a step of blending the cosmetic blending agent.

The method for producing a cosmetic of the present invention comprises a step of combining a base that forms an ammonium cation with an acid that forms an anion, wherein the base and the acid form an organic ammonium salt composed of the ammonium cation represented by the following formula (I) and the anion.

N⁺[R¹]_n[R²]_4-n (I)

In the formula (I), R¹Each independently represents a hydroxyalkyl group having 1 or more hydroxyl groups, having an alkyl moiety of 1 to 10 carbon atoms in a straight or branched chain state, and containing or not containing an oxygen atom in the alkyl moiety, a carboxyalkyl group having 1 or more carboxyl groups, having an alkyl moiety of 1 to 10 carbon atoms in a straight or branched chain state, and containing or not containing an oxygen atom in the alkyl moiety, or a hydroxycarboxyalkyl group having 1 or more hydroxyl groups and 1 to 10 carbon atoms in a straight or branched chain state, and containing or not containing an oxygen atom in the alkyl moiety, R²Each independently represents a hydrogen atom or a linear or branched alkyl group having 1 to 18 carbon atoms, and at least one of the groups represents a hydrogen atom. n represents an integer of 0 to 4.

ADVANTAGEOUS EFFECTS OF INVENTION

According to the cosmetic compounding agent of the present invention, the cosmetic using the cosmetic compounding agent and the method for producing the cosmetic, the cosmetic compounding agent is retained without volatilization, and the effects of the active ingredient can be exhibited efficiently, with excellent short-term and long-term water retention and moisture retention, affinity to hair, skin, and the like, high safety, and excellent feeling in use, and with improved solubility and permeability of the active ingredient.

Further, when the cosmetic compounding agent is a hair treatment agent, it is possible to provide a hair treatment agent which has high adhesion to hair, excellent water retention, affinity, and antistatic properties, and good use feeling such as finger combing property, flexibility, touch, elasticity, toughness, thickening property, cohesiveness, moist feeling, gloss, smoothness, and non-stickiness, and which has excellent adhesion to protein contained in hair, stability, thermal stability, and solubility of an active ingredient, and a hair treatment composition using the hair treatment agent.

When the cosmetic compounding agent is a skin care agent, it has excellent short-term and long-term water retention and moisture retention properties, excellent barrier properties against skin moisture, good feeling in use such as moisture retention, stickiness, and skin compatibility, excellent skin affinity and permeability, and high safety to the skin. Further, a skin care agent having high solubility of the active ingredient and excellent whitening effect and antistatic property, and a skin care composition using the skin care agent can be provided.

Drawings

Fig. 1A is a photograph of hair appearance after air-drying and an SEM image of the hair surface observed in the evaluation of table 14.

Fig. 1B is a photograph of hair appearance after air-drying and an SEM image of the hair surface observed in the evaluation of table 14.

Fig. 2 is a photograph showing the appearance of hair after air-drying in the evaluation in table 16.

Fig. 3 is a photograph showing the appearance of hair after air-drying in the evaluation in table 17.

Detailed Description

The present invention will be described in detail below.

1. Cosmetic compounding agent

The cosmetic compounding agent of the present invention is mainly intended for a substance to be compounded as a raw material in a cosmetic as a product.

The cosmetic compounding agent is not particularly limited, and examples thereof include a hair treatment agent compounded as a raw material in a hair treatment composition which is a product suitable for hair and the like, and a skin care agent compounded as a raw material in a skin care composition which is a product suitable for skin and the like. The hair is not particularly limited, and examples thereof include human hair such as hair, beard, eyebrow, eyelash, nose hair, ear hair, axillary hair, and body hair. The skin care agent is not particularly limited, and examples thereof include skin, keratin, nails, mucous membranes in the oral cavity and nasal cavity, and the cosmetic compounding agent of the present invention can be applied to cosmetics for these subjects.

The cosmetic compounding agent of the present invention contains an organic ammonium salt having a hydrogen-bonding functional group in at least either one of a cation and an anion.

In the present invention, the organic ammonium salt contains an organic cation having a nitrogen atom as an ion center or NH₄ ⁺And an organic anion.

1-1. cation

As the organic ammonium salt cation, there is no particular oneExamples of the cation include cations having a nitrogen atom as the ion center, and examples thereof include ammonium cations (organic ammonium cations NR substituted with an organic group)₄ ⁺(at least one R is an organic group and the others are hydrogen atoms) and NH₄ ⁺) The organic ammonium salt cation in which the nitrogen atom as the cation is substituted with an organic group other than the ammonium cation is preferably an imidazolium cation, a pyridinium cation, a pyrrolidinium cation, a piperidinium cation, a pyrrolinium cation, a pyrazinium cation, a triazolium cation, an isoquinolinium cation, an oxazolinium cation (oxazolinium), a thiazolinium cation, a morpholinium cation, a guanidinium cation, a pyrimidinium cation, a piperazinium cation, a triazinium cation, a quinolinium cation, an indolinium cation, a quinoxalinium cation, an isoxazolium cation, a cationic amino acid, or the like. Among them, ammonium cation, imidazolium cation, pyridinium cation, pyrrolidinium cation, piperidinium cation, and morpholinium cation are preferable, and ammonium cation is more preferable. The cations exemplified herein are collectively referred to as "cations having a basic structure" as described above and also including a substituent such as a hydrogen-bonding functional group.

It is preferred that the organic ammonium salt used in the present invention has a hydrogen-bonding functional group in the cation.

The hydrogen-bonding functional group is not particularly limited, and examples thereof include an oxygen-containing group, a nitrogen-containing group, a sulfur-containing group, a phosphorus-containing group, and a hydrogen atom directly bonded to nitrogen.

The oxygen-containing group is not particularly limited, and examples thereof include a hydroxyl group, a carbonyl group, an ether group, an ester group, an aldehyde group, a carboxyl group, a carboxylate group, a urea group, a urethane group, an amide group, an oxazole group, a morpholine group, a urethane group, and a urethane group.

The nitrogen-containing group is not particularly limited, and examples thereof include an amino group and a nitro group.

The sulfur-containing group is not particularly limited, and examples thereof include a sulfuric acid group (-O-S (-O)₂-O-), sulfonyl (-S (═ O)₂O-), sulfonic acid group(-S(＝O)₂-), a mercapto group (-SH), a thioether group (-S-), a thiocarbonyl group (-C (═ S) -), a thiourea group (-N-C (═ S) -N-), a thiocarboxyl group (-C (═ S) OH), a thiocarboxylate group (-C (═ S) O-), a dithiocarboxyl group (-C (═ S) SH), a dithiocarboxylate group (-C (═ S) S-), and the like.

Examples of the phosphorus-containing group include, but are not particularly limited to, a phosphoric acid group (-O-P (-O) (-O-), a phosphonic acid group (-O) (-O-), a phosphinic acid group (-P (-O) -O-), a phosphorous acid group (-O-P (-O-), a phosphinic acid group (-P-O-), a pyrophosphoric acid group (-O-P (-O) (-O-))₂―O-]And the like.

Among them, the hydrogen-bonding functional group in the cation is preferably a hydroxyl group, a carboxyl group, a carboxylate group, an ester group, a carbonyl group, an ether group, or a hydrogen atom directly bonded to nitrogen. Among these, a hydroxyl group, a carboxyl group, a carboxylate group, an ether group, and a hydrogen atom directly bonded to nitrogen are more preferable, a hydroxyl group, a carboxyl group, a carboxylate group, and a hydrogen atom directly bonded to nitrogen are further preferable, and a hydroxyl group and a hydrogen atom directly bonded to nitrogen are particularly preferable. Examples of the substituent having a hydrogen-bonding functional group include a hydroxyalkyl group, a carboxyalkyl group, a hydroxycarboxyalkyl group, an alkyl ester group, and an alkyl ether group.

The hydroxyalkyl group has 1 or more hydroxyl groups, and the alkyl moiety is preferably a straight-chain or branched-chain, preferably straight-chain, having 1 to 10 carbon atoms, more preferably 1 to 6 carbon atoms, and still more preferably 1 to 4 carbon atoms, and the alkyl moiety may or may not contain an oxygen atom.

The carboxyalkyl group has 1 or more hydroxyl groups, and the alkyl moiety is preferably a straight-chain or branched, preferably straight-chain, having 1 to 10 carbon atoms, more preferably 1 to 6 carbon atoms, and still more preferably 1 to 5 carbon atoms, and the alkyl moiety may or may not contain an oxygen atom.

The hydroxycarboxyalkyl group has 1 or more hydroxyl groups and carboxyl groups, and the alkyl moiety is preferably a linear or branched, preferably linear, having 1 to 10 carbon atoms, more preferably 1 to 6 carbon atoms, and still more preferably 1 to 5 carbon atoms, and the alkyl moiety may or may not contain an oxygen atom.

Where the alkyl moiety contains an oxygen atom, the oxygen atom may form or contain, for example, an ether bond, carbonyl group, hydroxyl group, carboxylate group, ester bond, amide bond, urea bond or urethane bond at the alkyl moiety. Therefore, in the present invention, the phrase "the alkyl moiety contains an oxygen atom" includes a case where the alkyl moiety is interrupted by a group which is an atomic group containing an oxygen atom and also contains a heteroatom such as a nitrogen atom, or a case where a hydrogen atom is substituted.

Examples of the hydroxyalkyl group include a monohydroxyalkyl group and a polyhydroxyalkyl group, and each alkyl group may contain an oxygen atom. Specific examples thereof are not particularly limited, and examples thereof include hydroxyalkyl, hydroxyalkoxyalkyl, alkoxyhydroxyalkyl, hydroxypolyalkyleneoxyalkyl and the like.

The monohydroxyalkyl group is not particularly limited, and examples thereof include hydroxymethyl, 1-hydroxyethyl, 2-hydroxyethyl, 1-hydroxypropan-1-yl, 2-hydroxypropan-1-yl, 3-hydroxypropan-1-yl, 1-hydroxypropan-2-yl, 2-hydroxypropan-2-yl, 1-hydroxybutan-1-yl, 2-hydroxybutan-1-yl, 3-hydroxybutan-1-yl, 4-hydroxybutan-1-yl, 1-hydroxy-2-methylpropan-1-yl, 2-hydroxy-2-methylpropan-1-yl, 3-hydroxy-2-methylpropan-1-yl, 2-hydroxy-2-methylpropan-1-yl, and the like, 1-hydroxybutan-2-yl, 2-hydroxybutan-2-yl, 3-hydroxybutan-2-yl, 4-hydroxybutan-2-yl, 1-hydroxy-2-methylpropan-2-yl, 1-dimethyl-2-hydroxyethyl, 5-hydroxypentan-1-yl, 6-hydroxyhexan-1-yl, 7-hydroxyheptan-1-yl, 8-hydroxyoctan-1-yl, 9-hydroxynonan-1-yl, 10-hydroxydecan-1-yl and the like. The monohydroxyalkyl group is preferably a monohydroxyalkyl group having 1 to 10 carbon atoms in the alkyl portion, more preferably a monohydroxyalkyl group having 1 to 6 carbon atoms, still more preferably a monohydroxyalkyl group having 1 to 4 carbon atoms, and particularly preferably a monohydroxyalkyl group having 1 to 3 carbon atoms.

The polyhydroxyalkyl group is not particularly limited, and examples thereof include di-, tri-, tetra-, penta-, hexa-, hepta-, or octahydroxyalkyi groups. Specific examples thereof include, but are not particularly limited to, dihydroxyethyl groups such as 1, 2-dihydroxyethyl group; 1-dihydroxypropan-1-yl groups such as 1, 2-dihydroxypropan-1-yl group and 2, 3-dihydroxypropan-1-yl group; a dihydroxypropan-2-yl group such as a1, 2-dihydroxypropan-2-yl group or a1, 3-dihydroxypropan-2-yl group; trihydroxypropan-1-yl; trihydroxypropan-2-yl; a dihydroxybutan-1-yl group such as 1, 2-dihydroxybutan-1-yl group, 1, 3-dihydroxybutan-1-yl group, 1, 4-dihydroxybutan-1-yl group, 2, 3-dihydroxybutan-1-yl group, 2, 4-dihydroxybutan-1-yl group, or 3, 4-dihydroxybutan-1-yl group; trihydroxybutane-1-yl groups such as 1, 2, 3-trihydroxybutane-1-yl group, 1, 2, 4-trihydroxybutane-1-yl group, 1, 3, 4-trihydroxybutane-1-yl group, and 2, 3, 4-trihydroxybutane-1-yl group; tetrahydroxybutane-1-yl; dihydroxy-2-methylpropan-1-yl group such as 1, 2-dihydroxy-2-methylpropan-1-yl group, 1, 3-dihydroxy-2-methylpropan-1-yl group, and 2, 3-dihydroxy-2-methylpropan-1-yl group; trihydroxy-2-methylpropan-1-yl; tetrahydroxy-2-methylpropan-1-yl; a dihydroxybutan-2-yl group such as 1, 2-dihydroxybutan-2-yl group, 1, 3-dihydroxybutan-2-yl group, 1, 4-dihydroxybutan-2-yl group, 2, 3-dihydroxybutan-2-yl group, 2, 4-dihydroxybutan-2-yl group, 3, 4-dihydroxybutan-2-yl group, etc.; trihydroxybutane-2-yl groups such as 1, 2, 3-trihydroxybutane-2-yl group, 1, 2, 4-trihydroxybutane-2-yl group, 1, 3, 4-trihydroxybutane-2-yl group, and 2, 3, 4-trihydroxybutane-2-yl group; tetrahydroxybutane-2-yl; 1, 3-dihydroxy-2-methylpropan-2-yl, 1, 3-dihydroxy-2-ethylpan-2-yl, 1, 3-dihydroxy-2-hydroxymethylpropane-2-yl; di, tri, tetra or pentahydroxypentan-1-yl; di, tri, tetra, penta or hexahydroxyhex-1-yl; di, tri, tetra, penta, hexa or heptahydroxyheptan-1-yl; di, tri, tetra, penta, hexa, hepta or octahydroxyoctan-1-yl, and the like. The number of hydroxyl groups in the polyhydroxyalkyl group is preferably 2 to 8, more preferably 2 to 4, and further preferably 2 to 3. The number of carbon atoms in the alkyl moiety is preferably 1 to 6, more preferably 1 to 4. n is preferably an integer of 1 to 2.

Further, a branched polyhydroxyalkyl group represented by the following formula is exemplified as a preferable group.

In the formula, R¹¹Represents a hydrogen atom, a linear alkyl group having 1 to 4 carbon atoms or a linear monohydroxyalkyl group having 1 to 4 carbon atoms.

Among the above polyhydroxyalkyl groups, 2, 3-dihydroxypropan-1-yl, 1, 3-dihydroxypropan-2-yl, 1, 3-dihydroxy-2-methylpropan-2-yl, 1, 3-dihydroxy-2-ethylpropan-2-yl, 1, 3-dihydroxy-2-hydroxymethylpropan-2-yl and pentahydroxyhexan-1-yl are preferred.

Examples of the carboxyalkyl group include a monocarboxyalkyl group and a polycarboxyalkyl group, and specific examples thereof include carboxyalkyl groups obtained by substituting a hydroxyl group of the above-exemplified mono-, di-, tri-, tetra-, penta-, hexa-, hepta-or octahydroxyalkyl group with a carboxyl group (which may or may not contain an oxygen atom at the alkyl moiety).

The above-mentioned monocarboxyalkyl group is not particularly limited, and examples thereof include a carboxymethyl group, a 1-carboxyethyl group, a 2-carboxyethyl group, a 1-carboxypropane-1-yl group, a 2-carboxypropane-1-yl group, a 3-carboxypropane-1-yl group, a 1-carboxypropane-2-yl group, a 2-carboxypropane-2-yl group, a 1-carboxybutane-1-yl group, a 2-carboxybutane-1-yl group, a 3-carboxybutane-1-yl group, a 4-carboxybutane-1-yl group, a 1-carboxy-2-methylpropan-1-yl group, a 2-carboxy-2-methylpropan-1-yl group, a 3-carboxy-2-methylpropan-1-yl group, and the like, 1-carboxybutan-2-yl group, 2-carboxybutan-2-yl group, 3-carboxybutan-2-yl group, 4-carboxybutan-2-yl group, 1-carboxy-2-methylpropan-2-yl group, 5-carboxypentan-1-yl group, 6-carboxyhexan-1-yl group, 7-carboxyheptan-1-yl group, 8-carboxyoctan-1-yl group, 9-carboxynonan-1-yl group, 10-carboxydecan-1-yl group and the like. The carboxyalkyl group is preferably a carboxyalkyl group having 1 to 10 carbon atoms in the alkyl moiety, more preferably a carboxyalkyl group having 1 to 6 carbon atoms, and still more preferably a carboxyalkyl group having 1 to 5 carbon atoms.

The hydroxycarboxyalkyl group is not particularly limited, and examples thereof include hydroxycarboxyalkyl groups (containing or not containing an oxygen atom at the alkyl position) in which a part of the hydroxyl groups of the above exemplified di-, tri-, tetra-, penta-, hexa-, hepta-or octahydroxyalkyl groups are replaced with carboxyl groups. Examples of the monohydroxycarboxyalkyl group having one hydroxyl group and one carboxyl group include a 2-hydroxy-3-carboxybutan-1-yl group (carnitine), a 1-hydroxyethyl-2-carboxyethyl group (serine), and a 2-hydroxyethyl-2-carboxyethyl group (threonine). As hydroxycarboxyalkyl, 2-hydroxy-3-carboxybutan-1-yl (carnitine) is preferred. The hydroxycarboxyalkyl group is preferably a hydroxycarboxyalkyl group having 1 to 10 carbon atoms in the alkyl moiety, more preferably a hydroxycarboxyalkyl group having 1 to 6 carbon atoms, and still more preferably a hydroxycarboxyalkyl group having 1 to 5 carbon atoms.

The alkyl ester group is not particularly limited, and examples thereof include those obtained by esterifying the carboxyl group of the above-exemplified carboxyalkyl group. Examples of the monoalkylester group having one ester group include a 1-acetoxy-ethan-2-yl group (acetylcholine), a 1-ethoxyethan-2-yl group and the like. As the alkyl ester group, 1-acetoxy-ethan-2-yl (acetylcholine) is preferred.

Examples of the functional group other than the hydrogen-bonding functional group in the cation include an alkyl group. The alkyl group is preferably a linear or branched alkyl group having 1 to 18 carbon atoms, more preferably a linear or branched alkyl group having 1 to 12 carbon atoms, still more preferably a linear or branched alkyl group having 1 to 8 carbon atoms, and yet more preferably a linear or branched alkyl group having 1 to 4 carbon atoms. The alkyl group is not particularly limited, and examples thereof include a methyl group, an ethyl group, a propan-1-yl group, a propan-2-yl group, a butan-1-yl group, a 2-methylpropan-1-yl group, a butan-2-yl group, a 2-methylpropan-1-yl group, a pentan-1-yl group, a 1-methylbutan-1-yl group, a 2-methylbutan-1-yl group, a 3-methylbutan-1-yl group, a 1-ethylbutan-1-yl group, a1, 1-dimethylpropane-1-yl group, a1, 2-dimethylpropane-1-yl group, a2, 2-dimethylpropane-1-yl group, a hexan-1-yl group, a heptan-1-yl group, a, Octane-1-yl, nonan-1-yl, decan-1-yl, dodecane-1-yl, tetradecan-1-yl, hexadecan-1-yl, octadecan-1-yl, etc.

It is also one of preferable embodiments that all cations of the organic ammonium salt used in the present invention are substituted with alkyl groups, and it is preferable that the cations of the organic ammonium salt used in the present invention have an alkyl group having 1 or more hydrogen-bonding functional groups and/or a hydrogen atom directly bonded to nitrogen, from the viewpoint of the effect of the present invention, that is, the water and moisture retention. In this case, it is preferable that at least one of the sites (nitrogen sites, carbon sites constituting a ring together with nitrogen, and the like atoms included in the chemical structure as the basic skeleton) of the cation, at which a functional group can be introduced, is substituted with an alkyl group having a hydrogen-bonding functional group, and the other sites are substituted with alkyl groups. Further, the hydrogen-bonding group is more preferably composed only of an alkyl group having a hydrogen-bonding functional group and/or a hydrogen atom directly bonded to nitrogen, and more preferably contains 1 or more hydrogen atoms directly bonded to nitrogen. Particularly preferred is a cation having a cationic structure composed of an alkyl group having a hydrogen-bonding functional group and a hydrogen atom directly bonded to nitrogen.

The hydrogen-bonding functional group is preferably a hydroxyl group.

As the cation of the organic ammonium salt, an ammonium cation, an imidazolium cation, a pyridinium cation, a pyrrolidinium cation, a piperidinium cation, or a morpholinium cation is preferable, and an ammonium cation is more preferable.

For the cosmetic compounding agent of the present invention, it is preferable that the cation of the organic ammonium salt is an ammonium cation represented by the following formula (I).

N⁺[R¹]_n[R³]_4-n (I)

In the formula (I), R¹Each independently represents a hydroxyalkyl group having 1 or more hydroxyl groups, having an alkyl moiety of 1 to 10 carbon atoms in a straight or branched chain state, and containing or not containing an oxygen atom in the alkyl moiety, a carboxyalkyl group having 1 or more carboxyl groups, having an alkyl moiety of 1 to 10 carbon atoms in a straight or branched chain state, and containing or not containing an oxygen atom in the alkyl moiety, or a hydroxycarboxyalkyl group having 1 or more hydroxyl groups and 1 to 10 carbon atoms in a straight or branched chain state, and containing or not containing an oxygen atom in the alkyl moiety, R²Each independently represents a hydrogen atom or a linear or branched alkyl group having 1 to 18 carbon atoms, and n represents an integer of 0 to 4.

[1] In the formula (I), n is preferably an integer of 1 to 4.

[2]In the above-mentioned [1]In, R²Preferably a hydrogen atom.

[3]In the above-mentioned [1]In, R¹Preferably, the alkyl moiety is a straight or branched monohydroxyalkyl group or a monocarboxyalkyl group having 1 to 10 carbon atoms. The number of carbon atoms in the alkyl moiety of the monohydroxyalkyl group is preferably 1 to 6, more preferably 1 to 4, and the number of carbon atoms in the alkyl moiety of the monocarboxyalkyl group is preferably 1 to 6, more preferably 1 to 5. Among them, monohydroxyalkyl groups are preferable.

[4]In the above-mentioned [3]In, R²Preferably a hydrogen atom.

[5]In the above-mentioned [1]In, R²Preferably a linear or branched alkyl group having 1 to 18 carbon atoms. The alkyl group is preferably a carbon number of 1 to 18, more preferably a carbon number of 1 to 12, further preferably a carbon number of 1 to 8, and particularly preferably a carbon number of 1 to 4.

[6]In the above-mentioned [1]Among them, R is preferred¹At least one of them has 2 or more hydroxyl groups, and the alkyl part is a straight-chain or branched-chain polyhydroxyalkyl group having 1 to 10 carbon atoms. The number of hydroxyl groups is preferably 2 to 8, more preferably 2 to 4, and further preferably 2 to 3. The number of carbon atoms in the alkyl moiety is preferably 1 to 6, more preferably 1 to 4. n is preferably an integer of 1 to 2.

[7]In the above [6 ]]In, R²Preferably a hydrogen atom.

1-2. anions

The anion of the organic ammonium salt used in the present invention is not particularly limited, and examples thereof include halogen-based anions, sulfur-based anions, phosphorus-based anions, cyanide-based anions, boron-based anions, fluorine-based anions, nitrogen oxide-based anions, and carboxylic acid-based anions, among which halogen-based anions, sulfur-based anions, boron-based anions, and carboxylic acid-based anions are preferable, halogen-based anions, sulfur-based anions, and carboxylic acid-based anions are more preferable, and carboxylic acid-based anions are even more preferable.

The halogen anion is not particularly limited, and examples thereof include chloride, bromide, and iodide.

The sulfide anion is not particularly limited, and examples thereof include a sulfonate anion, a hydrogen sulfonate anion, an alkyl sulfonate anion (e.g., methane sulfonate, ethyl sulfonate, butyl sulfonate, benzene sulfonate, p-toluene sulfonate, 2, 4, 6-trimethylbenzene sulfonate, styrene sulfonate, 3-sulfopropylmethacrylate anion, 3-sulfopropylacrylate anion, etc.), a sulfate anion, a hydrogen sulfate anion, and an alkyl sulfate anion (e.g., methyl sulfate anion, ethyl sulfate anion, butyl sulfate anion, octyl sulfate anion, 2- (2-methoxyethoxy) ethyl sulfate anion, etc.).

The phosphorus-based anion is not particularly limited, and examples thereof include a phosphate anion, a hydrogenphosphate anion, a dihydrogenphosphate anion, a phosphonate anion, a hydrogenphosphonate anion, a dihydrogenphosphonate anion, a phosphinate anion, a hydrogenphosphinate anion, an alkylphosphate anion (e.g., dimethylphosphate, diethylphosphate, dipropylphosphate anion, dibutylphosphate anion, etc.), an alkylphosphonate anion (e.g., methylphosphonate anion, ethylphosphonate anion, propylphosphonate anion, butylphosphonate anion, methylmethylphosphonate anion, etc.), an alkylphosphinate anion, and a hexaalkylphosphate anion.

The cyano anion is not particularly limited, and examples thereof include tetracyanoborate anion, dicyanamide anion, thiocyanate anion, isothiocyanate anion, and the like.

The boron-based anion is not particularly limited, and examples thereof include tetraalkylborate anions such as tetrafluoroborate anion, bisoxalato borate anion, and tetraphenylborate anion.

The fluorine-based anion is not particularly limited, and examples thereof include a bis (fluorosulfonyl) imide anion, a bis (perfluoroalkylsulfonyl) imide anion (e.g., a bis (trifluoromethylsulfonyl) imide anion, a bis (pentafluoroethylsulfonyl) imide, a bis (heptafluoropropanesulfonyl) imide anion, a bis (nonafluorobutylsulfonyl) imide, etc.), a perfluoroalkylsulfonate anion (e.g., a trifluoromethanesulfonate anion, a pentafluoroethanesulfonate anion, a heptafluoropropanesulfonate anion, a perfluorobutylsulfonate (nonaflate) anion, a perfluorooctanesulfonate anion, etc.), a fluorophosphate anion (e.g., a hexafluorophosphate anion, a tris (pentafluoroethyl) trifluorophosphate anion, etc.), a tris (perfluoroalkylsulfonyl) methide anion (e.g., a tris (trifluoromethanesulfonyl) methide anion, a tris (perfluoroalkylsulfonyl) methide anion, etc.), a bis (perfluoroalkylsulfonyl) imide anion, etc, Tris (pentafluoroethanesulfonyl) methide anion, tris (heptafluoropropanesulfonyl) methide anion, tris (nonafluorobutanesulfonyl) methide anion, etc.), fluorohydride anion, etc.

In view of the effect of the present invention, that is, in obtaining water retention and moisture retention, boron anions containing a halogen atom or halogen anions can be used as the anion, and when used as a liquid at 25 ℃, boron anions containing a halogen atom are more preferable.

In view of the effect of the present invention, that is, in obtaining water retention and moisture retention, when the anion is a halogen atom-containing boron anion or halogen anion, the anion is preferably a bromide ion, and more preferably a halogen atom-containing boron anion, as compared with a chloride ion.

The nitroxide anion is not particularly limited, and examples thereof include a nitrate anion and a nitrite anion.

The above-mentioned carboxylic acid anion is an anion having at least 1 or more carboxylic acids (-COO)^-) The organic acid anion of (2) may or may not contain an oxygen-containing group, a nitrogen-containing group, a sulfur-containing group or a phosphorus-containing group, and among the oxygen-containing groups, an oxygen-containing group is preferable, and a hydroxyl group and a carboxyl group are more preferable, and a hydroxyl group is further preferable. Examples of the carboxylic acid anion include, but are not particularly limited to, saturated aliphatic carboxylic acid anions, unsaturated aliphatic carboxylic acid anions, alicyclic carboxylic acid anions, aromatic carboxylic acid anions, saturated aliphatic hydroxycarboxylic acid anions, unsaturated aliphatic hydroxycarboxylic acid anions, alicyclic hydroxycarboxylic acid anions, aromatic hydroxycarboxylic acid anions, carbonyl carboxylic acid anions, alkyl ether carboxylic acid anions, halogenated carboxylic acid anions, and amino acid anions. (the carbon number of the carboxylic acid anion exemplified below includes the carbon of the carboxyl group)

The saturated aliphatic carboxylic acid anion is composed of a linear or branched aliphatic saturated hydrocarbon group and 1 or more carboxylic acid anions, and preferably has 1 to 22 carbon atoms, with or without a carboxyl group or a carboxylate group. Specific examples of the anion include, but are not particularly limited to, anions obtained by dissociating protons from formic acid, acetic acid, propionic acid, butyric acid, valeric acid, caproic acid, enanthic acid, caprylic acid, pelargonic acid, capric acid, lauric acid, myristic acid, pentadecanoic acid, palmitic acid, margaric acid, stearic acid, arachidic acid, heneicosanoic acid, behenic acid, isobutyric acid, 2-methylbutyric acid, isovaleric acid, 2-ethylhexanoic acid, isononanoic acid, isopalmitic acid, isostearic acid, oxalic acid, malonic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid, and the like.

The unsaturated aliphatic carboxylic acid anion is composed of a linear or branched aliphatic unsaturated hydrocarbon group and 1 or more carboxylic acid anions, contains or does not contain a carboxyl group or a carboxylate group, and preferably has 3 to 22 carbon atoms. Specific examples of the anion include, but are not particularly limited to, anions obtained by dissociating protons from acrylic acid, methacrylic acid, crotonic acid, palmitoleic acid, oleic acid, octadecenoic acid, linoleic acid, linolenic acid, eleostearic acid, arachidonic acid, maleic acid, fumaric acid, and the like.

The alicyclic carboxylic acid anion is composed of an aromatic-free saturated or unsaturated carbocyclic ring and 1 or more carboxylic acid anions, and preferably has 6 to 20 carbon atoms. Among them, alicyclic carboxylic acid anions having a cyclohexane ring skeleton are preferable, and specific examples thereof are not particularly limited, and examples thereof include anions obtained by dissociating a proton from a cyclohexane carboxylic acid or a cyclohexane dicarboxylic acid.

The aromatic carboxylic acid anion is composed of an aromatic monocyclic ring or a plurality of rings and 1 or more carboxylic acid anions, and preferably has 6 to 20 carbon atoms. Among them, aromatic carboxylic acid anions having a benzene ring skeleton are preferable, and specific examples thereof are not particularly limited, and include anions obtained by dissociating protons from benzoic acid, cinnamic acid, phthalic acid, isophthalic acid, terephthalic acid, and the like.

The saturated aliphatic hydroxycarboxylic acid anion is composed of a straight or branched aliphatic saturated hydrocarbon group, 1 or more carboxylic acid anions, and 1 or more hydroxyl groups, and preferably contains 2 to 24 carbon atoms, with or without a carboxyl group or a carboxylate group. Among them, a saturated aliphatic hydroxycarboxylic acid anion having 1 to 4 hydroxyl groups and having 2 to 7 carbon atoms is preferable. Specific examples of the anion include, but are not particularly limited to, anions obtained by dissociating a proton from glycolic acid, lactic acid, tartronic acid, glyceric acid, glycolic acid, hydroxybutyric acid, 2-hydroxydecanoic acid, 3-hydroxydecanoic acid, 12-hydroxystearic acid, dihydroxystearic acid, cerebronic acid, malic acid, tartaric acid, citramalic acid, citric acid, isocitric acid, leucine, mevalonic acid, pantoic acid, and the like.

The unsaturated aliphatic hydroxycarboxylic acid anion is composed of a straight-chain or branched aliphatic unsaturated hydrocarbon group, 1 or more carboxylic acid anions, and 1 or more hydroxyl groups, and preferably has 3 to 22 carbon atoms. Specifically, the anion is not particularly limited, and examples thereof include anions obtained by dissociating a proton from ricinoleic acid (ricinolic acid), and ricinoleic acid.

The alicyclic hydroxycarboxylic acid anion is composed of a saturated or unsaturated carbocyclic ring having no aromatic group, 1 or more carboxylic acid anions, and 1 or more hydroxyl groups, and preferably has 4 to 20 carbon atoms. Among them, alicyclic hydroxycarboxylic acid anions having a six-membered ring skeleton with 1 to 4 hydroxyl groups are preferable, and specific examples thereof are not particularly limited, and examples thereof include anions obtained by dissociating a proton from hydroxycyclohexane carboxylic acid, dihydroxycyclohexane carboxylic acid, quinic acid (1, 3, 4, 5-tetrahydroxycyclohexane carboxylic acid), shikimic acid, and the like. Further, an anion obtained by dissociating a proton from a cyclic lactone having a hydroxyl group can also be preferably used, and specific examples thereof are not particularly limited, and include anions obtained by dissociating a proton from ascorbic acid, erythorbic acid, and the like.

The aromatic hydroxycarboxylic acid anion is composed of an aromatic monocyclic ring or a plurality of rings, 1 or more carboxylic acid anions, and 1 or more hydroxyl groups, and preferably has 6 to 20 carbon atoms. Among them, aromatic carboxylic acid anions having a benzene ring skeleton with 1 to 3 hydroxyl groups are preferable, and specific examples thereof are not particularly limited, and include anions obtained by dissociating protons from salicylic acid, hydroxybenzoic acid, dihydroxybenzoic acid, trihydroxybenzoic acid, hydroxymethylbenzoic acid, vanillic acid, syringic acid, protocatechuic acid (ピロトカテク acid, protocatechuic acid), gentisic acid, bryozoac acid, mandelic acid, benzilic acid, atrolactic acid, phloroglucinic acid, coumaric acid, umbellic acid, caffeic acid, ferulic acid, sinapic acid, and the like.

The carbonyl carboxylic acid anion is a carboxylic acid anion having a carbon number of 3 to 22 and having a carbonyl group in a molecule, and preferably a carbonyl carboxylic acid anion having a carbon number of 3 to 7 and having 1 to 2 carbonyl groups. Among them, preferred is the compound represented by CH₃((CH₂)pCO(CH₂)_q)COO^-(p and q represent an integer of 0 to 2) is a carbonyl carboxylic acid anion. Specifically, the anion is not particularly limited, and examples thereof include anions obtained by dissociating a proton from levulinic acid, pyruvic acid, and the like.

The alkyl ether carboxylic acid anion is a carboxylic acid anion having 2 to 22 carbon atoms and having an ether group in the molecule, and preferably an alkyl carboxylic acid anion having 1 to 2 ether groups and 2 to 12 carbon atoms. Among them, preferred is the compound represented by CH₃(CH₂)_rO(CH₂)_sCOO^-(r and s are an integer of 0 to 4) and an anion of an alkyl ether carboxylic acid or an anion of a polyoxyethylene alkyl ether carboxylic acid. Specifically, the anion is not particularly limited, and examples thereof include anions obtained by dissociating a proton from methoxyacetic acid, ethoxyacetic acid, methoxybutyric acid, ethoxybutyric acid, and the like.

The halogenated carboxylic acid anion is preferably a halogenated carboxylic acid anion having 2 to 22 carbon atoms. Specific examples thereof include, but are not limited to, anions obtained by dissociating protons from fluorine-substituted halogenated carboxylic acids such as trifluoroacetic acid, trichloroacetic acid, tribromoacetic acid, pentafluoropropionic acid, pentachloropropionic acid, pentabromopropionic acid, perfluorononanoic acid, perchloronanoic acid, and perbromonanoic acid.

The amino acid anion is not particularly limited, and examples thereof include anions obtained by dissociating a proton from glycine, alanine, glutamic acid, N-acetyl glutamic acid, arginine, asparagine, aspartic acid, isoleucine, glutamine, histidine, cysteine, leucine, lysine, proline, phenylalanine, threonine, serine, tryptophan, tyrosine, methionine, valine, sarcosine, aminobutyric acid, methylleucine, aminocaprylic acid, aminocaproic acid, glutamic acid, aminopentanoic acid, aminoisobutyric acid, thyroxine, creatine, ornithine, opine amino acid, theanine, tricholomine, kainic acid, domoic acid, amanithine, Acromelic acid (Acromelic acid), cystine, hydroxyproline, phosphoserine, desmosine, and the like.

In the effect of the present invention, that is, in the hair treatment agent, adhesion to hair, water retention and moisture retention, affinity, antistatic property, adhesion to protein of hair and stabilization, stability to heat, solubility of active ingredients, sensory properties such as finger combing property, flexibility, touch, elasticity, toughness, thickening property, cohesiveness, moist feeling, luster, smoothness and non-stickiness of hair, the anion is preferably a halogen anion, a sulfur anion, a phosphorus anion, a cyano anion, a nitrogen oxide anion or a carboxylic acid anion, and among them, a halogen anion, a sulfur anion, a phosphoric acid anion, a boron anion or a carboxylic acid anion is preferable, a carboxylic acid anion or a halogen anion is more preferable, and a carboxylic acid anion is still more preferable.

In the present invention, namely, the effects of the skin care agent, that is, short-term and long-term water retention and moisture retention of the skin care agent, barrier properties against skin moisture, antistatic properties, high solubility of a specific active ingredient, functionalities such as sustained moisturizing feel, non-adhesion, skin compatibility, high affinity for skin, permeability, low irritation, high safety, and whitening effects, the anion is preferably a sulfide anion, a phosphorus anion, a nitrogen oxide anion, a carboxylic acid anion, or a halogen anion, more preferably a sulfide anion, a phosphorus anion, or a carboxylic acid anion, still more preferably a phosphorus anion, a carboxylic acid anion, and particularly preferably a carboxylic acid anion.

The halogen-based anion, sulfur-based anion, phosphorus-based anion, cyanide-based anion, nitrogen oxide-based anion, boron-based anion, carboxylic acid-based anion, and the like are preferable, among which halogen-based anion, sulfur-based anion, phosphoric acid-based anion, boron-based anion, and carboxylic acid-based anion are preferable, halogen-based anion, sulfur-based anion, phosphoric acid-based anion, and carboxylic acid-based anion are more preferable, and carboxylic acid-based anion is further preferable.

Among the carboxylic acid anions, hydrophilic carboxylic acid anions are preferable in terms of water retention and moisture retention effects, and such carboxylic acid anions have preferably 8 or less carbon atoms, and more preferably 6 or less carbon atoms. The anion preferably has a hydrogen-bonding functional group, and the functional group preferably contains a group capable of bonding hydrogen bonds, such as an oxygen-containing group, a nitrogen-containing group, a sulfur-containing group, or a phosphorus-containing group. Specifically, a hydroxyl group, an amino group, a carbonyl group, a carboxyl group, a carboxylate group, a sulfonyl group, a sulfate group, a phosphate group, and a phosphate group are preferable, and among them, a hydroxyl group, a carboxyl group, a carboxylate group, a sulfonyl group, and a phosphate group are more preferable, a hydroxyl group, a carboxyl group, and a carboxylate group are further preferable, and a hydroxyl group is particularly preferable. The anion of a carboxylic acid having a carbon number of 8 or less is not particularly limited, but is preferably a formate anion, an acetate anion, a propionate anion, a butyrate anion, a valerate anion, a hexanoate anion, a heptanoate anion, an octanoate anion, an oxalate anion, a malonate anion, a succinate anion, a glutarate anion, a adipate anion, a pimate anion, a suberate anion, an acrylate anion, a methacrylate anion, a crotonate anion, a cyclohexanecarboxylate anion, a benzoate anion, a phthalate anion, a isophthalate anion, a terephthalate anion, a glycolate anion, a lactate anion, a tartronate anion, a glycerate anion, a hydroxyacetate anion, a hydroxybutylate anion, a cerebronelate anion, a malate anion, a, Tartrate anion, citramalate anion, citrate anion, isocitrate anion, leucine anion, mevalonate anion, pantoate anion, hydroxycyclohexane carboxylate anion, dihydroxycyclohexane carboxylate anion, quinic acid (1, 3, 4, 5-tetrahydroxycyclohexane carboxylate) anion, shikimate anion, salicylate anion, hydroxybenzoate anion, dihydroxybenzoate anion, trihydroxybenzoate anion, hydroxymethylbenzoate anion, vanillic acid anion, syringic acid anion, protocatechuate anion, gentisic acid anion, orchitic acid anion, mandelic acid anion, levulinic acid anion, pyruvate anion, methoxyacetate anion, ethoxyacetate anion, methoxybutyrate anion, ethoxybutyrate anion, trifluoroacetate anion, mandelate anion, hydroxy benzoate, or a hydroxy benzoate or hydroxy benzoate, or hydroxy benzoate or a hydroxy benzoate or a hydroxy benzoate or a salt, or a, Trichloro chloride anion, tribromoacetic acid anion, pentafluoropropionic acid anion, pentachloropropionic acid anion, pentabromopropionic acid anion, glycine anion, alanine anion, glutamic acid anion, N-acetylglutamic acid anion, arginine anion, asparagine anion, aspartic acid anion, isoleucine anion, glutamine anion, histidine anion, cysteine anion, leucine anion, lysine anion, proline anion, threonine anion, serine anion, methionine anion, valine anion, sarcosine anion, aminobutyrate anion, methylleucine anion, aminooctanoic acid anion, aminocaproic acid anion, pentaglycine anion, aminoisobutyric acid anion, sarcosine anion, ornithine anion, crown gall amino acid anion, pentaacetic acid anion, aminoisobutyric acid anion, sarcosine anion, ornithine anion, crown gall amino acid anion, and the like, Theanine anion, tricholoma matsutake amino anion, amanitic acid anion, cystine anion, hydroxyproline anion, and phosphoserine anion, as the carboxylic acid anion having a carbon number of 6 or less, more preferably a formic acid anion, an acetic acid anion, a propionic acid anion, a butyric acid anion, a glutaric acid anion, a hexanoic acid anion, an oxalic acid anion, a malonic acid anion, a succinic acid anion, a glutaric acid anion, a adipic acid anion, an acrylic acid anion, a methacrylic acid anion, a crotonic acid anion, a cyclohexane carboxylic acid anion, a glycolic acid anion, a lactic acid anion, a tartronic acid anion, a glyceric acid anion, a glycolic acid anion, a hydroxybutyric acid anion, a cerebronic acid anion, a malic acid anion, a tartaric acid anion, a citramalic acid anion, a citric acid anion, an isocitric acid anion, a leucine anion, a citric acid anion, a malic acid anion, a succinic acid anion, a salt of a carboxylic acid, a salt of a carboxylic acid, a salt of a carboxylic acid, a salt of a compound, a salt of a compound, a salt of a compound, a salt of a compound, a salt of a compound, a salt of a compound, a salt of a compound, a salt of a compound, a salt of a compound, a salt of a compound, a salt of a compound, a salt, a compound, Mevalonate anion, pantoate anion, hydroxycyclohexanecarboxylic acid anion, dihydroxycyclohexanecarboxylic acid anion, levulinic acid anion, pyruvic acid anion, ethoxyacetic acid anion, methoxybutyric acid anion, ethoxybutyric acid anion, trifluoroacetic acid anion, trichloroacetic acid anion, tribromoacetic acid anion, pentafluoropropionic acid anion, pentachloropropionic acid anion, pentabromopropionic acid anion, glycine anion, alanine anion, glutamic acid anion, N-acetylglutamic acid anion, arginine anion, asparagine anion, aspartic acid anion, isoleucine anion, glutamine anion, histidine anion, cysteine anion, leucine anion, lysine anion, proline anion, threonine anion, serine anion, glycine anion, N-acetyl-glutamic acid anion, arginine anion, glycine anion, proline anion, threonine anion, serine anion, glycine anion, methionine anion, valine anion, sarcosine anion, aminobutyrate anion, methylleucine anion, aminohexanoate anion, pentanoate anion, aminopentanoate anion, aminoisobutyrate anion, creatine anion, ornithine anion, opine amino acid anion, theanine anion, tricholoma amino acid anion, amanitic acid anion, cystine anion, hydroxyproline anion, phosphoserine anion, as the carboxylic acid anion having a hydroxyl group, glycolic acid anion, lactic acid anion, tartronic acid anion, glycerate anion, glycolic acid anion, hydroxybutyric acid anion, cerebronate anion, malic acid anion, tartaric acid anion, citrate anion, citric acid anion, isocitric acid anion, leucine anion, mevalonate anion, malic acid anion, citric acid anion, isocitric acid anion, leucine anion, malic acid anion, etc, A pantoate anion, a hydroxycyclohexane carboxylate anion, a dihydroxycyclohexane carboxylate anion, a quinic acid (1, 3, 4, 5-tetrahydroxycyclohexane carboxylic acid) anion, a shikimate anion, a salicylate anion, a hydroxybenzoate anion, a dihydroxybenzoate anion, a trihydroxybenzoate anion, a hydroxymethylbenzoate anion, a vanillic acid anion, a syringic acid anion, a protocatechuic acid anion, a gentisic acid anion, a bryozoate anion, a mandelate anion, a tricholoma acid anion, a shiitake mushroom amino acid anion, a hydroxyproline anion, a serine anion, a threonine anion, and among them, a glycolate anion, a lactate anion, a malate anion, a tartrate anion, a citrate anion, and a quinic acid anion are more preferable.

In order to further enhance the effect of the present invention, the organic ammonium salt used in the present invention is particularly preferably an organic salt having a hydrogen-bonding functional group in both a cation and an anion.

On the other hand, lipophilic carboxylic acid anions are preferable for maintaining the moisturizing effect of the skin care agent, barrier properties, solubility of oil-soluble components, improvement of stability of the emulsion composition, improvement of feeling in use, cleansing action, and skin moisturizing, and examples of such carboxylic acid anions include saturated and unsaturated aliphatic carboxylic acid anions having 1 carboxylic acid anion depending on the number of substituents such as hydroxyl group, and the carbon number is preferably 8 or more, more preferably 12 or more, and still more preferably 18 or more. Specific examples of the lipophilic carboxylic acid anion are not particularly limited, and examples thereof include an octanoic acid anion, a nonanoic acid anion, a decanoic acid anion, a lauric acid anion, a myristic acid anion, a pentadecanoic acid anion, a palmitic acid anion, a heptadecanoic acid anion, a stearic acid anion, an isostearic acid anion, an arachic acid anion, a heneicosanic acid anion, a behenic acid anion, a palmitic acid anion, an oleic acid anion, an octadecenoic acid anion, a linolic acid anion, and a linolenic acid anion, and more preferably an oleic acid anion, an linolic acid anion, and an isostearic acid anion.

1-3. supplementary notes on cations and anions

The organic ammonium salt used in the cosmetic compounding agent of the present invention is preferably a natural compound as either one or both of a cation and an anion, from the viewpoint of safety. Examples of the cation include, but are not particularly limited to, choline cation, acetylcholine cation, thioacetylcholine cation, carnitine cation, betaine, sultaine, ethyl (2-methoxyethyl) dimethylammonium cation, benzyl cinchona (benzyl cincinnidinium), carbamoyl- β -methylcholine cation, etc., and examples of the anion include citric acid anion, lactic acid anion, malic acid anion, ascorbic acid anion, glycolic acid anion, tartaric acid anion, quinic acid anion, acetic acid anion, butyric acid anion, adipic acid anion, caprylic acid anion, capric acid anion, succinic acid anion, oleic acid anion, linoleic acid anion, alanine anion, glycine anion, etc., and amino acids that can be used for both the cation and the anion, examples thereof include glycine, alanine, glutamic acid, N-acetyl glutamic acid, arginine, asparagine, aspartic acid, isoleucine, glutamine, histidine, cysteine, leucine, lysine, proline, phenylalanine, threonine, serine, tryptophan, tyrosine, methionine, valine, sarcosine, aminobutyric acid, methylleucine, aminocaprylic acid, aminocaproic acid, glutamic acid, aminopentanoic acid, aminoisobutyric acid, thyroxine, creatine, ornithine, crown gall amino acid, theanine, tricholoma acid, kainic acid, domoic acid, amanitoic acid (Acromelic acid), cystine, hydroxyproline, phosphoserine, and desmosine. The combination of the cation and the anion is not particularly limited, and specific examples thereof include triacetate, triisostearate, trioleate, trilinoleate, trilactate, triethanolamine, trisuccinate, trimalt, tritartrate, trifumarate, triascorbate, tricitrate, 2-amino-2-methyl-1, 3-propanediol acetate, 2-amino-2-methyl-1, 3-propanediol isostearate, 2-amino-2-methyl-1, 3-propanediol oleate, 2-amino-2-methyl-1, 3-propanediol linoleate, 2-amino-2-methyl-1, 3-propanediol lactate, 2-amino-2-methyl-1, 3-propanediol glycolate, 2-amino-2-methyl-1, 3-propanediol succinate, 2-amino-2-methyl-1, 3-propanediol malate, 2-amino-2-methyl-1, 3-propanediol tartrate, 2-amino-2-methyl-1, 3-propanediol fumarate, 2-amino-2-methyl-1-propanol lactate, gamma-aminobutyric acid lactate, epsilon-aminocaproic acid lactate, monoethanolamine lactate, diethanolamine glycolate, diethanolamine succinate, 2-amino-1, 3-propanediol acetate, 2-amino-1, 3-propanediol glycolate, 2-amino-1, 3-propanediol succinate, 2-amino-1, 3-propanediol citrate, triethanolamine lactate, triethanolamine glycolate, triethanolamine citrate, 2-amino-1, 3-propanediol lactate, 2-amino-2-ethyl-1, 3-propanediol lactate, 1-amino-1-deoxy-D-glucitol lactate, ammonium lactate salt, tetraethanolamine lactate, tris (2, 3-dihydroxypropyl) -1-hydroxy-2- (hydroxymethyl) -2-butaneammonium lactate.

Examples thereof include choline methanesulfonate, choline phosphate, choline hypophosphite, choline hydrochloride, and the like, and particularly, preferable examples thereof include both cations and anions of natural systems, and choline acetate, choline glycolate, choline lactate, choline succinate, choline tartrate, choline ascorbate, and the like.

From the viewpoint of safety, when the cation has a monohydroxyalkyl group, a triethanolammonium cation or a diethanolammonium cation is preferable, and a triethanolammonium cation is particularly preferable.

In addition, from the viewpoint of safety and use, the organic ammonium salt used in the present invention is preferably a compound described in japanese quasi-drug raw material standards (external standard), japanese quasi-drug additive standards, japanese pharmacopoeia (japanese pharmacopoeia office of prescriptions) (daily bureau), japanese non-pharmacopoeia quasi-drug standards (external standard), pharmaceutical additive standards (pharmaceutical additive standard), or food additive specifications (dietary supplement) as a raw material (for example, an acid or an alkali), and more preferably a compound described in japanese quasi-drug raw material standards, japanese pharmacopoeia standard, japanese non-pharmacopoeia quasi-drug standards, pharmaceutical additive standards, organic ammonium salts described in food additive specifications, and organic ammonium salts described in japanese quasi-drug raw material standards as a raw material constituting either one or both of a cation and an anion. The cation is not particularly limited, and for example, monoethanol ammonium cation, diethanol ammonium cation, triethanol ammonium cation, 2-amino-2-hydroxymethyl-1, 3-propanediol ammonium cation, 2-amino-2-methyl-1-propanol ammonium cation, and 2-amino-2-methyl-1, 3-propanediol ammonium cation are preferable, and from the viewpoint of low odor, 2-amino-2-hydroxymethyl-1, 3-propanediol ammonium cation and 2-amino-2-methyl-1, 3-propanediol ammonium cation are more preferable. Examples of the anion include acetate anion, octanoate anion, decanoate anion, laurate anion, myristate anion, palmitate anion, stearate anion, oleate anion, linoleate anion, lactate anion, glycolate anion, succinate anion, citrate anion, chloride anion, fumarate anion, phosphate anion, and ascorbate anion. Examples of the amino acid that can be used in the cation or anion include glycine, alanine, arginine, aspartic acid, histidine, cysteine, proline, serine, tryptophan, tyrosine, methionine, aminobutyric acid, aminocaproic acid, cystine, glutamic acid, isoleucine, phenylalanine, threonine, tryptophan, methionine, valine, and theanine.

1-4. organic ammonium salt and cosmetic compounding agent

The organic ammonium salt of the cosmetic compounding agent of the present invention may be in an anhydrous state (anhydrous substance) or may be a hydrate which absorbs moisture in the air. The hydrate is a compound which absorbs water when the compound is left in the air at 25 ℃ and the water content of which reaches a saturated state. The compound which does not absorb water when left at 25 ℃ in the air is free of hydrate and is an anhydrate.

When the organic ammonium salt used in the present invention is a hydrate, evaporation of water in the hydrate is suppressed, and the effect of retaining water and keeping moisture for a long period of time is sustained. Therefore, when the organic ammonium salt used in the present invention is dissolved with water exceeding the water of hydration and left in the air to observe the reduction of water, the rate of reduction of water decreases with time because the evaporation of the water of hydration is suppressed.

The organic ammonium salt used in the present invention may be any of a liquid and a solid at 25 ℃, when the anhydride and the hydrate are liquid at 25 ℃, the anhydride, the hydrate and the diluted product of the organic ammonium salt of these liquids do not cause problems in use such as crystallization, aggregation and solidification of the organic ammonium salt, and when the cosmetic compounding agent is a hair treatment agent, immediately after use, after other solvents and water mixed are volatilized, the organic ammonium salt is also nonvolatile, and is uniformly applied as a liquid on the hair surface, whereby the effects of the present invention such as moisture retention, adhesion, antistatic property (antistatic property), stabilization of hair protein, and the like, and the effects of the dissolved additive can be more effectively and longer-term exhibited. In addition, from the viewpoint of adhesion of the hair treatment agent, the blending molar ratio of the acid forming the organic ammonium salt to the base is preferably 1: 5-5: 1, more preferably 1: 1. when the cosmetic compounding agent is a skin care agent, the organic ammonium salt is not volatile immediately after use and after the other mixed solvent and water are volatilized, and is uniformly applied as a liquid on the skin surface, whereby the effects of the present invention, such as water retention and moisture retention, antistatic property (antistatic property), high affinity to the skin, and high solubility of the active ingredient, and the effects of the dissolved additive can be exerted more effectively and for a longer period of time. The cosmetic compounding agent is preferably at a pH of 3 to 10, more preferably at a pH of 5 to 9, and even more preferably at a pH of 6 to 8, from the viewpoints of safety of skin, hair, and the like and prevention of damage. For example, at a pH of 3 to 10, the molar ratio of the acid to the base to be incorporated in the organic ammonium salt is 2: 1-1: 5, at a pH of 5-9, is 1: 2-1: 1, at a pH of 6-8, is 1: 1.

the cosmetic can exert the effects of the organic ammonium salt or the components dissolved in the organic ammonium salt on the objects including hair and skin more effectively and for a longer period of time. For example, even when a composition containing a low concentration is used in a small amount, the effects thereof can be sufficiently exhibited. When the liquid is a liquid at 25 ℃, other additives (for example, a poorly soluble active ingredient) can be used as a base, a solvent, or a carrier in the object. The organic ammonium salt is naturally excellent in permeability of the dissolved active ingredient to hair and skin. From the viewpoint of solubility of the active ingredient, the blending molar ratio of the acid to the base of the organic ammonium salt constituting the cosmetic compounding agent is preferably 1: 1-2: 1, more preferably 1: 1. the melting point (freezing point) of the organic ammonium salt used in the present invention is preferably less than 25 deg.C, more preferably less than-5 deg.C, and particularly preferably less than-10 deg.C.

The organic ammonium salt used in the present invention is excellent in permeability into objects including hair and skin, is useful for a water-retaining and moisture-retaining effect, and can be used as a carrier for an active ingredient.

The organic ammonium salt used in the present invention does not volatilize even in a low humidity environment, remains as a moisture, and retains moisture for a long period of time, and is preferable from the viewpoint of maintaining the moisture retention and retention effect for a long period of time. In order to impart the water-retaining and moisturizing effect to hair, the surface of hair has a negative charge, and therefore the organic ammonium salt of the present invention can be immobilized on the surface of hair for a long period of time by the cationic interaction. In addition, when applied to the skin, the compound of the present invention is preferable because the hydrogen-bonding functional group has a high affinity for (binds to) an amino residue such as a hydroxyl group, a carbonyl group, or an amino group of a protein on the skin surface, and the compound is favorably applied to the skin and immobilized for a long period of time, and has a small molecular size and a high permeability. Further, when the surface of the skin has a negative charge, the cationic interaction of the organic ammonium salt of the present invention is preferable in that the organic ammonium salt can be immobilized on the surface of the skin for a long period of time.

In addition, since the protein on the hair surface has a functional group that interacts with and binds to a hydrogen-bonding functional group or a hydrogen atom, such as an oxygen-containing group, a nitrogen-containing group, a sulfur-containing group, or a phosphorus-containing group, which the organic ammonium salt of the present invention has, the organic ammonium salt having a hydrogen-bonding functional group in a cation and/or an anion binds to and interacts with, for example, a carboxyl group, a carbonyl group, or an amino group of the hair, and thus can be immobilized well for a long period of time.

The organic ammonium salt used in the cosmetic compounding agent of the present invention has excellent hydrophilicity, small molecular size and high permeation pressure, and therefore has excellent permeability to, for example, skin, hair and the like. The organic ammonium salt used in the present invention is preferably one having a salt structure and a hydrogen-bonding functional group, and is therefore easily adsorbed because the surface of the skin or the like is negatively or positively charged and the surface of the hair or the like is negatively charged.

The cosmetic compounding agent of the present invention has high water retentivity and is nonvolatile, and therefore, has excellent barrier properties and can prevent long-term drying. In particular, the melting point is low, and the barrier property is higher in the case of being liquid at 25 ℃. In addition, the cosmetic compounding agents (hair treatment agents, skin care agents) of the present invention are (1) prepared by mixing an alkali or an acid group with a solvent as necessary to produce an organic ammonium salt and, as necessary, mixing other components; (2) in the case where the organic ammonium is not produced in advance, the base and the acid are mixed as respective components with a solvent and other components as necessary to form an organic ammonium salt in the system, thereby making it possible to obtain a cosmetic compounding agent (hair treatment agent, skin care agent).

The cosmetic compounding agent of the present invention is mainly intended for a substance to be compounded as a raw material in a cosmetic as a product.

The cosmetic compounding agent is not particularly limited, and examples thereof include a hair treatment agent compounded as a raw material in a hair treatment composition which is a product applied to hair or the like, and a skin care agent compounded as a raw material in a skin care composition which is a product applied to skin or the like.

In the cosmetic compounding agent of the present invention, a hair treatment agent is compounded as a raw material in a hair treatment composition which is a product applied to hair such as shampoo. The hair treatment agent of the present invention may be the organic ammonium salt or the hydrate thereof described above, and the raw material may be a composition containing the organic ammonium salt. When the hair treatment agent of the present invention is a composition, the content of the organic ammonium salt is preferably 0.01% by mass or more, more preferably 0.1% by mass or more, further preferably 1.0% by mass or more, and particularly preferably 10.0% by mass or more in terms of an anhydride. The form of the composition is not particularly limited, and examples thereof include those obtained by dissolving or dispersing the organic ammonium salt in water, a solvent, or the like.

In the cosmetic compounding agent of the present invention, a skin care agent is compounded as a raw material in a skin care composition which is a product applied to the skin such as a cosmetic lotion. The skin care agent of the present invention may be the organic ammonium salt or the hydrate thereof described above, and the compounding ingredient may be a composition containing the organic ammonium salt. When the skin care agent of the present invention is a composition, the content of the organic ammonium salt is preferably 0.001% by mass or more, more preferably 0.01% by mass or more, further preferably 0.1% by mass or more, particularly preferably 1.0% by mass or more, more particularly preferably 10.0% by mass or more in terms of anhydrous substance, and the form of the composition is not particularly limited, and examples thereof include a composition in which the organic ammonium salt is dissolved or dispersed in water, a solvent, or the like.

The cosmetic compounding agent of the present invention may be prepared by mixing water, a solvent, and other components after preparing an organic ammonium salt in advance to form a cosmetic compounding agent or a cosmetic, or may be prepared by mixing each compound as a raw material of cation or anion with water, a solvent, and other components to form a cosmetic compounding agent or a cosmetic.

Examples of the solvent include, but are not particularly limited to, water, methanol, ethanol, propanol, isopropanol, butanol, ethylene glycol, propylene glycol, 1, 3-butylene glycol, diethylene glycol, dipropylene glycol, isoprene glycol, hexylene glycol, glycerin, benzyl alcohol, methyl acetate, ethyl acetate, isopropyl acetate, diethyl ether, acetone, toluene, hexane, heptane, acetonitrile, and the like, and these solvents may be used in combination of 2 or more kinds as needed. The composition may contain additives, but is not particularly limited, and examples thereof include pH regulators, pigments, resin particles, surfactants, oils, viscosity regulators, colorants, preservatives, perfumes, ultraviolet absorbers (including organic and inorganic ones), natural plant extracts, seaweed extracts, crude drug ingredients, antioxidants, insect repellents, and the like.

The cosmetic compounding agent of the present invention can be adjusted in pH by adding a pH adjuster or the like as needed. The pH adjuster is not particularly limited, but is preferably a natural compound. Examples of the natural pH adjuster include various amino acids including citric acid, lactic acid, malic acid, glycolic acid, tartaric acid, quinic acid, acetic acid, butyric acid, caproic acid, caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, succinic acid, oleic acid, linoleic acid, adipic acid, trisodium citrate, glucono-delta-lactone, gluconic acid, potassium gluconate, sodium gluconate, monosodium succinate, disodium succinate, sodium acetate, potassium bitartrate, sodium lactate, sodium dihydrogen pyrophosphate, phosphoric acid, sodium phosphate, potassium carbonate, sodium bicarbonate, alanine, and glycine.

The organic ammonium salt used in the present invention can be appropriately selected from hydrophilic or lipophilic anions or cations depending on other components to be mixed and used and the desired effect. For example, hydrophilic organic ammonium salts are preferable in terms of water retention and moisture retention and dissolution of water-soluble active ingredients, and lipophilic organic ammonium salts of anions or cations are preferably used in terms of dissolution of skin-moisturizing effects and oil-soluble active ingredients.

Among the organic ammonium salts used in the present invention, the organic ammonium salt which is liquid at room temperature also functions as a solvent or medium for the other composition or the above-mentioned additive.

The organic ammonium salt used in the present invention has a hydrogen-bonding functional group such as an oxygen-containing group, a nitrogen-containing group, a sulfur-containing group, or a phosphorus-containing group in a cation and/or an anion, and therefore has an effect of stabilizing a higher-order structure of a protein such as keratin contained in hair, cutin, or nails. Hair is modified by a change in secondary structure, which is a higher-order structure of proteins such as keratin, or a structural change due to bond cleavage, and hair is damaged to impair texture. The hydrogen-bonding functional group in the organic ammonium salt used in the present invention can maintain a secondary structure by interacting with a protein such as keratin in hair, inhibit bond cleavage, inhibit modification of the protein, and maintain the texture after hair treatment. In addition, the effect of stabilizing the proteins of the scalp can be achieved.

The effect of the organic ammonium salt used in the present invention on proteins such as keratin in hair is exhibited not only in the neutral region (shampoo, etc.) but also in the acidic region (hair conditioner) and the alkaline region (hair dye).

In the cosmetic compounding agent of the present invention, the hair treatment agent has the effect of the organic ammonium salt of the present invention as described above, and therefore, when used for hair, it can impart flexibility, finger combing property, elasticity, toughness, thickening property, cohesiveness, moist feeling, smoothness and gloss of the surface, and exhibits functional effects such as excellent touch and less stickiness. The hair treatment agent of the present invention has the above-mentioned effects also on damaged hair damaged by drying or dyeing.

The organic ammonium salt used in the present invention has a hydrogen bonding functional group such as an oxygen-containing group, a nitrogen-containing group, a sulfur-containing group, a phosphorus-containing group, or the like in a cation and/or an anion, and therefore has excellent affinity with the skin, the cutin, the nail, or the mucous membrane, is nonvolatile, and therefore has excellent short-term and long-term water retention and moisture retention properties and excellent moisture barrier properties. Further, the composition is excellent in feeling of use such as moisture retention, stickiness, and skin compatibility, and also excellent in permeability and safety. In particular, when the compounds described in the japanese standard for quasi-drugs (external standard), japanese pharmacopoeia (japanese pharmacopoeia side) (daily office), japanese non-pharmacopoeia standard (office external standard), pharmaceutical additive standard (drug addition standard), japanese standard for quasi-drug additives, and food additive official book (dietary supplement) are used as raw materials, it is preferable to confirm safety by these standards. Further, the active ingredient has high solubility, and has excellent whitening effect and antistatic property. As described above, the ammonium salt used in the present invention interacts with proteins including keratin, can maintain secondary structures, can inhibit bond cleavage, and can inhibit modification of proteins. Therefore, the protein can be used for moisture retention and protein stabilization of skin, cutin, nail, and mucosa (oral cavity and nasal cavity).

By introducing a structure (acid, alkali) having a whitening effect, for example, into the cation and/or anion of the ammonium salt of the present invention to form an organic ammonium salt, these effects can be obtained continuously and efficiently from the viewpoints of non-volatility and permeability. Furthermore, although ascorbic acid has low stability, it can be stabilized by making it into an ammonium salt, and the effect can be further improved.

2. Can be added into cosmetic

The method for producing a cosmetic of the present invention includes the step of blending the cosmetic compounding agent of the present invention described above.

In this case, the cosmetic preparation is prepared by mixing the cosmetic compounding agent of the present invention prepared in advance as one of the components.

As another example, the method for producing a cosmetic of the present invention includes a step of blending an acid that forms an anion with a base that forms an ammonium cation, the base and the acid forming an organic ammonium salt composed of an ammonium cation represented by the following formula (I) and an anion.

N⁺[R¹]_n[R²]_4-n (I)

In the formula (I), R¹Each independently represents a hydroxyalkyl group having 1 or more hydroxyl groups, having an alkyl moiety of 1 to 10 carbon atoms in a straight or branched chain state, and containing or not containing an oxygen atom in the alkyl moiety, a carboxyalkyl group having 1 or more carboxyl groups, having an alkyl moiety of 1 to 10 carbon atoms in a straight or branched chain state, and containing or not containing an oxygen atom in the alkyl moiety, or a hydroxycarboxyalkyl group having 1 or more hydroxyl groups and 1 to 10 carbon atoms in a straight or branched chain state, and containing or not containing an oxygen atom in the alkyl moiety, R²Each independently represents a hydrogen atom or a linear or branched alkyl group having 1 to 18 carbon atoms, and at least one of the groups represents a hydrogen atom. n represents an integer of 0 to 4.

It is equivalent to: (1) preparing a cosmetic compounding agent (hair treatment agent, skin care agent) containing an organic ammonium salt obtained by mixing the base, the acid, and, if necessary, a solvent and other components, and then mixing the cosmetic compounding agent, and, if necessary, a solvent and other components to prepare a cosmetic (hair treatment composition, skin care composition); (2) the base and the acid are mixed as respective components with a solvent and other components as necessary without previously producing an organic ammonium salt, and an organic ammonium salt is formed in the system, thereby producing a cosmetic compounding agent (hair treatment agent, skin care agent) or a cosmetic (hair treatment composition, skin care composition).

As shown in (1), the method comprises producing a cosmetic preparation using the cosmetic compounding agent of the present invention in which a base forming a cation of at least 1R in the formula (I) and an acid forming the anion are compounded respectively²Is a hydrogen atom (especially R)²All hydrogen atoms).

In other words, the method comprises producing a cosmetic preparation using the cosmetic compounding agent of the present invention in which the base and the acid forming the organic ammonium salt in which at least one R in the formula (I) is contained are respectively compounded²Is a hydrogen atom (in particular, R)²All are hydrogen atoms). In this case, n in the formula (I) is preferably an integer of 0 to 3, more preferably an integer of 1 to 3. R¹May be a straight-chain or branched monohydroxyalkyl group or a monocarboxyalkyl group having 1 to 10 carbon atoms in the alkyl moiety, R¹At least one of the alkyl groups may be a straight-chain or branched polyhydroxyalkyl group having 2 or more hydroxyl groups and having 1 to 10 carbon atoms in the alkyl moiety.

As shown in (2), the production method further comprises preparing a cosmetic containing an organic ammonium salt by separately blending the base and the acid as respective components without previously preparing the organic ammonium salt.

Specific examples of the base include those obtained by removing one of the ammonium cations and R from the ammonium cation described in the above item "1-1. cation²And a base having a proton corresponding to the hydrogen atom of (3). In addition, hydroxides of cations in the organic ammonium salts of the present invention are also included.

The amine compound of the base is not particularly limited, and may include NH₃Organic amines substituted by organic radicals, e.g. NR₃(at least one of R is an organic group, and the others are hydrogen atoms) and imidazole, pyridine, pyrrolidine, piperidine, pyrroline, pyrazine, triazine, isoquinoline, oxazoline, dihydrothiazole, morpholine, guanidine, pyrimidine, piperazine, triazine, quinoline, indoline, quinoxaline, isoxazoline, amino acid, and the like. The amine compounds exemplified herein are collectively referred to as "amine compounds containing a substituent such as a hydrogen-bonding functional group in addition to the amines having the basic structure as described above.

Specific examples of the acid include acids obtained by adding a proton to the anion described in the section "1-2. anion".

The acid used in the present invention is not particularly limited, and various anions and proton compounds can be used, and examples of the anion include a sulfur anion, a phosphorus anion, a nitrogen oxide anion, and a carboxylic acid anion. Specific examples and preferred modes thereof are as described above.

3. Cosmetic preparation

The cosmetic of the present invention contains the cosmetic compounding agent of the present invention described above.

In the present invention, cosmetics are defined as substances applied to the body for the purpose of cleaning, beautifying the human body, enhancing charm, changing the appearance, or maintaining the health of the skin or hair by painting, spraying, or other similar methods to those, with reference to substances that mitigate the effects on the human body. Among them, cosmetics for hair, skin, and the like are preferable, and hair treatment compositions and skin care compositions are particularly preferable.

(Hair treatment composition)

The hair treatment composition of the present invention is mainly intended for products to be used for hair, which are blended with the hair treatment agent of the present invention described above. The hair is not particularly limited, and examples thereof include human body hair such as hair, beard, eyebrow, eyelash, nose hair, ear hair, axillary hair, and body hair.

The hair treatment composition of the present invention is not particularly limited, and examples thereof include a shampoo, a scalp shampoo, a conditioner-integrated shampoo, a conditioning shampoo, a color-protecting shampoo, a hair soap, a fading prevention shampoo, a dry-cleaning shampoo (non-rinsing shampoo), a rinse conditioner (rinse), a color conditioner, a hair cleanser, a conditioning agent, a color conditioner, a non-rinsing conditioner, a hair-setting agent, a styling agent (a styling agent), a styling agent (an hair-setting agent), a hair dressing, a hair oil, a hair spray, a mousse, a foam, a hair gel, a hair cream, a hair wax, a hair lotion, a hair tonic, a hair dye, a scalp conditioner, a mascara, an eyelash cosmetic, a eyebrow product, and a eyebrow pencil.

In the hair treatment composition of the present invention, in addition to the hair treatment agent and the solvent of the present invention, other components can be blended in the range not impairing the effects of the present invention, in consideration of the conventional blending and technical common knowledge in the above-mentioned applications. Such other components are not particularly limited and may be appropriately selected according to the purpose, and examples thereof include anionic surfactants, nonionic surfactants, cationic surfactants, amphoteric surfactants, cationic polymers, water-soluble polymers, viscosity modifiers, gloss-imparting agents, higher alcohols, polyols, higher fatty acids, amidoamines, hydrocarbons, waxes, esters, silicone derivatives, physiologically active ingredients, extracts, antioxidants, metal ion chelating agents, preservatives, ultraviolet absorbers (including organic and inorganic), perfumes, humectants, carbons, metal oxides, minerals, salts, neutralizers, pH regulators, pigments, resin particles, colorants, natural plant extracts, seaweed extracts, crude drug ingredients, moisture-releasing agents, insect repellents, Enzymes, and the like.

The anionic surfactant is not particularly limited, and examples thereof include fatty acid soaps, alkyl ether carboxylates, alkylene alkyl ether carboxylates, fatty acid amide ether carboxylates, acyl lactylates, N-acyl glutamates (e.g., coconut acyl glutamic acid triethanolamine, coconut acyl sodium glutamate), N-acyl alanates (e.g., sodium lauroyl alanine, sodium cocoyl alanine), N-acylmethyl- β -alanates (e.g., sodium lauroyl methyl- β -alaninate), N-acyl sarcosinates (e.g., sodium lauroyl sarcosinate, lauroyl sarcosinate triethanolamine), N-acyl threonine, N-acyl glycinate, N-acyl aspartic acid, N-acyl serine, N-acyl- ω -amino acid salts, and the like, Carboxylates such as alkyl sulfoacetate and alkenyl sulfoacetate, sulfonates such as alkane sulfonate, α -olefin sulfonate (e.g., tetradecene sodium sulfonate), α -sulfo fatty acid methyl ester salt, acyl isethionate, alkyl glycidyl ether sulfonate, alkyl sulfosuccinate, polyoxyalkylene alkyl sulfosuccinate (e.g., disodium laureth sulfosuccinate and disodium alkanol polyether sulfosuccinate), alkylbenzene sulfonate, alkylnaphthalene sulfonate, N-acyl taurate, N-acyl methyltaurate (e.g., sodium cocoyl methyltaurate), formalin condensate sulfonate, paraffin sulfonate, alkylamide sulfonate, alkenylamide sulfonate, and alkylglyceryl ether sulfonate, alkyl sulfate, alkenyl sulfate, alkyl ether sulfate, alkenyl ether sulfate, and alkyl glyceryl ether sulfate, Polyoxyalkylene alkyl ether sulfate (sodium polyoxyethylene lauryl ether sulfate, etc.), alkylaryl ether sulfate, fatty acid alkanolamide sulfate, fatty acid monoglyceride sulfate, and polyoxyalkylene alkyl ether sulfateSulfates such as alkylene fatty acid amide ether sulfate and alkyl glyceryl ether sulfate, phosphates such as polyoxyalkylene alkyl ether phosphate (e.g., sodium polyoxyethylene lauryl ether phosphate and potassium polyoxyethylene lauryl ether phosphate), alkyl phosphates, alkyl aryl ether phosphate and fatty acid amide ether phosphate, and the like, and examples of the nonionic surfactant include, but are not particularly limited to, fatty acid alkanolamides such as polyoxyalkylene fatty acid ester, polyoxyalkylene alkyl ether, polyoxyalkylene alkylphenyl ether, polyoxyalkylene (cured) castor oil ester, sucrose fatty acid ester, polyglycerol alkyl ether, polyglycerol fatty acid ester, alkyl alkanolamide, polyoxyethylene alkyl alkanolamide and polyoxypropylene alkyl alkanolamide, polyoxyalkylene glycerol fatty acid (mono/di/tri) ester, sorbitan fatty acid ester, and the like, Examples of the cationic surfactant include, but are not particularly limited to, primary amine salts, secondary amine salts, tertiary amine salts, aliphatic amidoamine salts, aliphatic amidoguanidinium salts, quaternary ammonium salts (e.g., stearyltrimethylammonium chloride, behenyltrimethylammonium chloride), alkyltrialkylenediol ammonium salts, alkyl ether ammonium salts, and other aliphatic amine salts and quaternary ammonium salts thereof, and cyclic quaternary ammonium salts such as benzalkonium salts, pyridinium salts, and imidazolium salts, and examples of the amphoteric surfactant include, but are not particularly limited to, alkyl betaine amphoteric surfactants, amidobetaine amphoteric surfactants (e.g., coconut oil fatty acid amidopropyl betaine, lauric amidopropyl betaine, myristic amidopropyl betaine, palm oil fatty acid amidopropyl betaine), and the like, Examples of the cationic polymer include, but are not particularly limited to, cationic starch, cationized cellulose, cationized hydroxyethyl cellulose, phosphate betaine amphoteric surfactant, imidazolium betaine amphoteric surfactant (2-alkyl-N-carboxymethyl-N-hydroxyethylimidazolium betaine, etc.), alkylamine oxide amphoteric surfactant, amino acid amphoteric surfactant, and phosphate amphoteric surfactant, and examples of the cationic polymer include, but are not limited to, cationic starch, cationized cellulose, cationized hydroxyethyl cellulose, and the like,Examples of the water-soluble polymer include, but are not particularly limited to, cationized guar gum, cationized locust bean gum, cationized tamarind gum, cationized tara gum, cationized fenugreek gum, (N, N-dimethyl-3, 5-dimethylenepiperidinium chloride) -acrylamide copolymer, poly (N, N-dimethyl-3, 5-methylenepiperidinium chloride), polyethyleneimine, quaternized vinylpyrrolidone-aminoethyl methacrylate copolymer, adipic acid-dimethylaminohydroxypropyldiethylenetriamine copolymer, acrylamide- β -methacryloyloxyethyltrimethylammonium copolymer, and the like, and examples of the water-soluble polymer include hydroxyethylcellulose, hydroxypropylcellulose, hydroxypropylmethylcellulose, dimethyldiallylammonium chloride-acrylamide copolymer, hydroxypropylcellulose acetate, and the like, Polyethylene glycol, high-polymer polyethylene glycol, polyvinyl alcohol, polyglutamic acid, carboxyvinyl polymer, acrylic acid-alkyl methacrylate copolymer, alkyl acrylate copolymer, etc., and examples of the viscosity modifier include, but are not particularly limited to, alkyl alkanolamides such as coconut oil fatty acid monoethanolamide, coconut oil fatty acid diethanolamide, lauric acid diethanolamide, coconut oil fatty acid N-methyl ethanolamide, etc., polyoxyethylene alkyl alkanolamides such as polyoxyethylene coconut oil fatty acid monoethanolamide, etc., and polyoxypropylene alkyl alkanolamides such as polyoxypropylene coconut oil fatty acid monoisopropanolamide, etc.; the water-soluble polymer, polysaccharide, cationic polymer, and the like are not particularly limited as the gloss imparting agent, and examples thereof include fatty acid ethylene glycol ester (ethylene glycol distearate, and the like), fatty acid polyethylene glycol ester, fatty acid monoethanolamide, and examples thereof include higher alcohols, cetyl alcohol, stearyl alcohol, and behenyl alcohol, examples thereof include polyhydric alcohols, and examples thereof include glycerin, 1, 3-butylene glycol, propylene glycol, dipropylene glycol, propane diol, sorbitol, diglycerin, triglycerol, and polyglycerin, and the like, and examples thereof include higher fatty acids, and examples thereof include myristic acid, palmitic acid, stearic acid, and behenic acid, and examples thereof include amidoamines, and are not particularly limited, and examples thereof include stearamidopropyl amide, and hydrocarbons, the solvent is not particularly limited, and examples thereof include a liquidExamples of the wax include, but are not particularly limited to, candelilla wax, carnauba wax, paraffin wax, microcrystalline wax, and polyethylene wax, examples of the ester include, but are not particularly limited to, animal and vegetable oils, isopropyl myristate, ethylhexyl palmitate, cetyl octanoate, cetyl ethylhexanoate, and isononyl isononanoate, examples of the silicone derivative include, but are not particularly limited to, dimethylpolysiloxane, methylphenylpolysiloxane, fatty acid-modified silicone, alcohol-modified silicone, amino-modified silicone, and dimethiconol, examples of the physiologically active ingredient include, but are not particularly limited to, natural plant extracts, seaweed extracts, and crude drug ingredients that impart a certain physiological activity to the skin when applied to the skin, the extracts are not particularly limited, and examples thereof include various extracts derived from plants, animals, and microorganisms, the antioxidants include, but are not particularly limited, tocopherol, dibutylhydroxytoluene, butylhydroxyanisole, gallic acid esters, and the like, and the metal ion chelating agents include, but are not particularly limited to, 1-hydroxyethane-1, 1-diphosphonic acid tetrasodium salt, ethylenediaminetetraacetic acid and salts thereof (dipotassium dihydrate salt, disodium calcium salt, trisodium salt, tetrasodium dihydrate salt, tetrasodium tetrahydrate salt, and the like), hydroxyethylethylenediaminetriacetic acid and salts thereof, phosphoric acid and salts thereof, ascorbic acid and salts thereof, succinic acid and salts thereof, gluconic acid and salts thereof, and the like, Polyphosphoric acid and its salt, metaphosphoric acid and its salt, tartaric acid and its salt, phytic acid and its salt, citric acid and its salt, maleic acid and its salt, polyacrylic acid and its salt, isopentene-maleic acid copolymer and its salt, silicic acid and its salt, hydroxybenzyl iminodiacetic acid and its salt, diethylene triamine pentaacetic acid and its salt, nitrilotriacetic acid and its salt, methylglycine diacetic acid and its salt, L-glutamic acid diacetic acid and its salt, L-aspartic acid diacetic acid and its salt, etc. as the preservative, there is no particular limitation, and for example, parabens (methyl paraben) are exemplifiedEthyl p-hydroxybenzoate, butyl p-hydroxybenzoate), 1, 2-alkanediol (carbon chain length 6-14) and derivatives thereof, phenoxyethanol, isopropyl methylphenol, sodium benzoate, hinokitiol, and the like, and the ultraviolet absorber is not particularly limited, and examples thereof include benzotriazole-based, PABA-based, anthranilic-based, cinnamic-based, salicylic-based, benzophenone-based, triazine-based, and the like, and the perfume is not particularly limited, and examples thereof include extracts, essential oils, resinoids, resins, floral oils, and combinations thereof, and the perfume includes perfume components as natural substances, and the moisturizer is not particularly limited, and examples thereof include mucopolysaccharides, hyaluronic acid, chondroitin sulfate, glutamic acid, chitosan, and the like, and the carbon-based is not particularly limited, and examples thereof include carbon black, and the like, Examples of the metal oxide include, but are not particularly limited to, graphite, carbon fiber, activated carbon, bamboo charcoal, single-walled carbon nanotube, double-walled carbon nanotube, multi-walled carbon nanotube, carbon nanohorn, fullerene, and carbon sphere, and examples of the metal oxide include silica, alumina (alumina), zirconia, titania, magnesia, Indium Tin Oxide (ITO), cobalt blue (CoO · Al), and the like₂O₃) Antimony oxide, zinc oxide, cesium oxide, zirconium oxide, yttrium oxide, tungsten oxide, vanadium oxide, cadmium oxide, tantalum oxide, niobium oxide, tin oxide, bismuth oxide, cerium oxide, copper oxide, iron oxide, indium oxide, boron oxide, calcium oxide, barium oxide, thorium oxide, indium tin oxide, magnesium silicate, ferrite, and the like, and salts thereof are not particularly limited, and examples thereof include salts of organic acids such as citric acid, malic acid, succinic acid, and lactic acid, and salts of inorganic acids such as hydrochloric acid, sulfuric acid, nitric acid, carbonic acid, and phosphoric acid, and examples thereof include inorganic acids, organic acids, alkali metal salts, and organic bases, and examples thereof include cleaning agents such as L-menthol, L-menthyl lactate, menthyl ether, menthanediol, camphor, peppermint oil, and the like, the insect repellent is not particularly limited, and examples thereof include delphene, and examples thereof include protease, cellulase, amylase, lipase, and glycerolMannanase, and the like.

The content of the hair treatment agent of the present invention in the hair treatment composition of the present invention is not particularly limited, but from the viewpoint of the effect of the present invention, the content of the organic ammonium salt is preferably 0.01% by mass or more, more preferably 0.1% by mass or more, further preferably 1.0% by mass or more, and particularly preferably 10.0% by mass or more in terms of an anhydride. As an example of the hair treatment composition of the present invention, for example, when the composition is prepared into a shampoo, the content of the hair treatment agent of the present invention is not particularly limited, and is preferably 0.1% by mass or more, more preferably 0.5% by mass or more, and further preferably 3.0% by mass or more. For example, when the hair treatment agent is prepared as a conditioning conditioner (conditioner), the content of the hair treatment agent of the present invention is not particularly limited, but is preferably 0.01% by mass or more, more preferably 0.1% by mass or more, further preferably 0.5% by mass or more, and particularly preferably 3.0% by mass or more.

The hair treatment composition of the present invention can be prepared by diluting the hair treatment agent of the present invention in a solvent so that the content thereof is, for example, in the above range. The solvent is not particularly limited, and examples thereof include alcohols such as water, methanol, ethanol, 1-propanol, 2-propanol, 1-butanol, and benzyl alcohol; alkyl ethers such as diethylene glycol monomethyl ether and diethylene glycol dimethyl ether; and polyhydric alcohols such as ethylene glycol, diethylene glycol, isoprene glycol, hexylene glycol, glycerin, diglycerin, 1, 3-butylene glycol, propylene glycol, dipropylene glycol, propane diol, sorbitol, and maltitol. These solvents may be used alone in 1 kind, or may be used in combination in 2 or more kinds. Among them, water or an aqueous solution is preferable, and water such as purified water is particularly preferable.

The hair treatment composition of the present invention can be produced, for example, by adding the hair treatment agent of the present invention and the other components to a solvent and mixing them. Heating to dissolve the solid raw materials, mixing, stirring and uniformly mixing according to requirements.

The hair treatment composition of the present invention may be prepared by mixing the organic ammonium salt used in the present invention with water, a solvent and other components in any order, without limitation, in addition to the manner in which the organic ammonium salt is prepared in advance and then mixed with water, a solvent and other components.

The hair treatment composition of the present invention can impart cohesiveness, a moist feeling, luster, and lubricity to hair and can provide a good touch without stickiness when used for hair, from the effects of short-term and long-term moisture retention and prevention of electrification (antistatic properties), protein adhesion to hair, stabilization, and thermal stability due to the non-volatility of the organic ammonium salt of the present invention contained therein. Further, the hair treatment composition can be excellent in solubility of the active ingredient.

(skin-care composition)

The skin care composition of the present invention is mainly intended for products suitable for skin and the like, which contain the skin care agent of the present invention described above. The skin and the like are not particularly limited, and examples thereof include skin, keratin, nail, mucous membrane in the oral cavity and nasal cavity.

The skin care composition is not particularly limited, and examples thereof include skin cleansing agents such as soap compositions, bath soaps, hand soaps, and facial cleansers; cleansing cosmetics such as cleansing oil, cleansing lotion, cleansing cream, cleansing gel, cleansing lotion, and the like; basic cosmetics such as astringent, moisturizer, lotion, beauty lotion, hand cream, body lotion, and body cream; makeup cosmetics such as pressed powder, foundation liquid, gel foundation, loose powder, mousse powder (mousse powder), concealer, blush, eye shadow, eyeliner, external application agent, lipstick, lip gloss, and foundation cream before makeup; sunscreen cosmetics such as sunscreen lotion and sunscreen cream; bath oil, bath lotion, and bath essence; examples of the cosmetic film include cosmetic films such as stain, whelk and concealer films, scalp care agents, nail cosmetics, keratin care products, oral care products, and sheet pack films, and the effects of the present invention are exhibited on the skin and the like in these applications.

The shape of the skin care composition of the present invention is not particularly limited, and may be uniform or non-uniform, and for example, it may be a liquid to solid state or an emulsion composition. The emulsion composition is not particularly limited, and examples thereof include a water-in-oil (W/O type) emulsion composition, an oil-in-water (O/W type) emulsion composition, and a composite emulsion (W/O/W type, O/W/O type).

The emulsion composition containing the skin care agent of the present invention is excellent in spreadability, non-stickiness, moisturizing feeling, skin compatibility, and feeling of use of any of skin elasticity when applied to the skin, and the organic ammonium salt used in the present invention is excellent in particularly sustained moisturizing feeling due to non-volatility. In particular, an emulsion composition containing an organic ammonium salt having a melting point of less than 25 ℃ is excellent in spreadability, stickiness, a moisturizing feeling, skin compatibility and other use feelings, and is particularly excellent in non-stickiness.

In the skin care composition of the present invention, in addition to the skin care agent and the solvent of the present invention, other components may be blended in the above-mentioned applications within a range not impairing the effects of the present invention, in view of conventional blending and technical common knowledge. Such other components are not particularly limited and may be appropriately selected according to the intended purpose, and examples thereof include anionic surfactants, nonionic surfactants, cationic surfactants, amphoteric surfactants, oils, cationic polymers, water-soluble polymers, viscosity modifiers, resin particles, gloss-imparting agents, higher alcohols, polyols, higher fatty acids, amidoamines, hydrocarbons, waxes, esters, silicone derivatives, physiologically active ingredients, extracts, antioxidants, preservatives, ultraviolet absorbers (including organic and inorganic), perfumes, humectants, carbons, metal oxides, minerals, salts, neutralizers, pH regulators, cleansing agents, insect repellents, enzymes, dyes, organic pigments, inorganic pigments, colorants, pearl essence (pearling agent), pearling agents (pearlizing agent), Anti-inflammatory agent, antioxidant, whitening agent, wrinkle improving agent, vitamins, amino acids, pilatory, antibacterial agent, hormone agent, plant extract, Sargassum extract, crude drug component, activator, blood circulation promoter, metal ion chelating agent, organic modified clay mineral, etc.

The anionic surfactant is not particularly limited, and examples thereof include fatty acid soaps, alkyl ether carboxylates, alkylene alkyl ether carboxylates, fatty acid amide ether carboxylates, acyl lactylates, N-acyl glutamates (e.g., coconut acyl glutamic acid triethanolamine, coconut acyl sodium glutamate), N-acyl alanates (e.g., sodium lauroyl alanine, sodium cocoyl alanine), N-acylmethyl- β -alanates (e.g., sodium lauroyl methyl- β -alaninate), N-acyl sarcosinates (e.g., sodium lauroyl sarcosinate, lauroyl sarcosinate triethanolamine), N-acyl threonine, N-acyl glycinate, N-acyl aspartic acid, N-acyl serine, N-acyl- ω -amino acid salts, and the like, Carboxylates such as alkyl sulfoacetate and alkenyl sulfoacetate, alkane sulfonates, α -olefin sulfonates (e.g., tetradecene sodium sulfonate), α -sulfo fatty acid methyl ester salts, acyl isethionates, alkyl glycidyl ether sulfonates, alkyl sulfosuccinates, polyoxyalkylene alkyl sulfosuccinates (e.g., disodium laureth sulfosuccinate and disodium alkanol polyether sulfosuccinate), alkylbenzene sulfonates, alkylnaphthalene sulfonates, N-acyl taurates, N-acyl methyltaurates (e.g., sodium cocoyl methyltaurate), formalin condensate sulfonates, paraffin sulfonates, alkylamide sulfonates, alkenylamide sulfonates, and alkylglyceryl ether sulfonates, alkyl sulfates, alkenyl sulfates, alkyl ether sulfates, alkenyl ether sulfates, and alkyl glyceryl ether sulfonates, The nonionic surfactant is not particularly limited, and examples thereof include polyoxyalkylene alkyl ether sulfate (e.g., sodium polyoxyethylene lauryl ether sulfate), alkylaryl ether sulfate, fatty acid alkanolamide sulfate, fatty acid monoglyceride sulfate, polyoxyalkylene fatty amide ether sulfate, and alkyl glyceryl ether sulfate, and phosphates such as polyoxyalkylene alkyl ether phosphate (e.g., sodium polyoxyethylene lauryl ether phosphate and potassium polyoxyethylene lauryl ether phosphate), alkyl phosphate, alkylaryl ether phosphate, and fatty acid amide ether phosphateExamples of the cationic surfactant include, but are not particularly limited to, alkylene fatty acid esters, polyoxyalkylene alkyl ethers, polyoxyalkylene alkylphenyl ethers, polyoxyalkylene (cured) castor oil esters, sucrose fatty acid esters, polyglycerol alkyl ethers, polyglycerol fatty acid esters, fatty acid alkanolamides such as alkyl alkanolamides, polyoxyethylene alkyl alkanolamides, and polyoxypropylene alkyl alkanolamides, polyoxyalkylene glycerin fatty acid (mono/di/tri) esters, sorbitan fatty acid esters, polyoxyalkylene sorbitan fatty acid esters, and alkylpolyglucosides, and the cationic surfactant includes, for example, primary amine salts, secondary amine salts, tertiary amine salts, aliphatic amide guanidinium salts, quaternary ammonium salts (e.g., stearyl trimethyl ammonium chloride and behenyl trimethyl ammonium chloride), alkyltrialkylene glycol ammonium salts, and the like, Examples of the amphoteric surfactant include, but are not particularly limited to, alkyl betaine amphoteric surfactants, amidobetaine amphoteric surfactants (e.g., coconut oil fatty acid amidopropyl betaine, lauric acid amidopropyl betaine, myristic acid amidopropyl betaine, palm kernel oil fatty acid amidopropyl betaine, etc.), sulfobetaine amphoteric surfactants (e.g., lauryl hydroxysulfobetaine), phosphate betaine amphoteric surfactants, imidazolium betaine amphoteric surfactants (e.g., 2-alkyl-N-carboxymethyl-N-hydroxyethylimidazolium betaine), alkyl amine oxide amphoteric surfactants, and cyclic quaternary ammonium salts such as benzalkonium salts, benzethonium salts, pyridinium salts, and imidazolium salts, Amino acid type amphoteric surfactants, phosphate type amphoteric surfactants, and the like. The oil agent is not particularly limited, and examples thereof include hydrocarbons, oils and fats, esters, fatty acids, higher alcohols, silicone oils, waxes, steroids, monomers, oligomers, polymers (high molecular compounds) having fluidity, silicone oils, alcohols, glycols, glycol ethers, cellosolves, and the like, and these may be any of liquids, gels, and solids at normal temperature. These substances may be used alone in 1 kind, or may be used in combination of 2 or more kinds. The hydrocarbon is not particularly limited, and examples thereof include liquid paraffin,Mineral oils such as paraffin, paraffin wax, light isoparaffin, light mobile isoparaffin, silosin (ceresin), microcrystalline wax, vaseline, white vaseline, mineral oil, squalane, alkylbenzene, polyethylene wax, polypropylene wax, hydrogenated polyisobutene, ethylene- α -olefin-co-oligomer, and ethylene-propylene polymer. Among other synthetic oils, aromatic oils are not particularly limited, and examples thereof include alkylbenzenes such as monoalkylbenzenes and dialkylbenzenes, monoalkylnaphthalenes, dialkylnaphthalenes, and polyalkylnaphthalenes, and aliphatic oils are not particularly limited, and examples thereof include normal paraffins, isoparaffins, polybutenes, polyisobutylenes, poly- α -olefins (such as 1-octene oligomers, 1-decene oligomers, and ethylene-propylene oligomers), and hydrogenated products thereof, and co-oligomers of α -olefins and ethylene. The ester-based oil is not particularly limited, and examples thereof include diester oils such as dibutyl sebacate, di (2-ethylhexyl) sebacate, dioctyl adipate, diisodecyl adipate, ditridecyl glutarate, and methyl acetyl ricinoleate, aromatic ester oils such as trioctyl trimellitate, tridecyl trimellitate, and tetraoctyl pyromellitate, polyol ester oils such as trimethylolpropane caprylate, trimethylolpropane pelargonate, pentaerythritol-2-ethylhexanoate, and pentaerythritol pelargonate, and complex ester oils such as oligo-esters of polyhydric alcohols and mixed fatty acids of dibasic acids and monobasic acids. The ether oil is not particularly limited, and examples thereof include phenyl ether oils such as monoalkyltriphenyl ether, alkyldiphenyl ether, dialkyldiphenyl ether, pentaphenyl ether, tetraphenyl ether, monoalkyltetraphenyl ether, and dialkyltetraphenyl ether. The fats and oils are not particularly limited, and examples thereof include avocado Oil, almond Oil, linseed Oil, olive Oil, cocoa butter, perilla Oil, tea seed Oil, castor Oil, sesame Oil, wheat germ Oil, rice bran Oil, camellia Oil, safflower Oil, soybean Oil, evening primrose Oil, tea seed Oil, corn Oil, rapeseed Oil, apricot seed Oil (Persic Oil), palm kernel Oil, coconut Oil, palm Oil, beef tallow, lard, horse fat, mutton tallow, shea butter, cocoa butter, sea tallow, and the likeTurtle oil, mink oil, egg yolk oil, oil of the urocanin gland (purcellin oil), castor oil, sunflower oil, jojoba oil, grape seed oil, macadamia nut oil, cottonseed oil, meadowfoam seed oil, coconut oil, peanut oil, cod liver oil, rose hip oil, hardened tallow oil, hardened castor oil, palm hardened oil, and the like. Examples of the esters include, but are not particularly limited to, alkyl stearate, alkyl palmitate, alkyl myristate, alkyl laurate, alkyl behenate, alkyl oleate, alkyl isostearate, alkyl 12-hydroxystearate, alkyl undecylenate, alkyl lanolate, alkyl erucate, alkyl cocoate, alkyl stearoyloxystearate, alkyl isononanoate, alkyl dimethyloctanoate, alkyl octanoate, alkyl lactate, alkyl ethylhexanoate, alkyl pivalate, alkyl malate, alkyl phthalate, alkyl citrate, alkyl malonate, alkyl adipate, ethylene glycol fatty acid ester, propylene glycol fatty acid ester, butylene glycol fatty acid ester, trimethylolpropane fatty acid ester, pentaerythritol fatty acid ester, polyglycerol fatty acid ester, polyglycerin fatty acid ester, glycerin fatty acid ester, trehalose fatty acid esters, pentanediol fatty acid esters, tris (2-ethylhexyl) trimellitate, and the like. The fatty acids are not particularly limited, and examples thereof include stearic acid, palmitic acid, myristic acid, lauric acid, behenic acid, oleic acid, isostearic acid, 12-hydroxystearic acid, undecylenic acid, lanolin fatty acid, erucic acid, and stearyloxystearic acid. The higher alcohols are not particularly limited, and examples thereof include lauryl alcohol, cetyl alcohol, cetostearyl alcohol, stearyl alcohol, oleyl alcohol, behenyl alcohol, lanolin alcohol, hexyldecanol, myristyl alcohol, arachidyl alcohol, phytosterol, isostearyl alcohol, and octyldodecanol. The silicone oil is not particularly limited, and examples thereof include amino-modified silicone oil, epoxy-modified silicone oil, carboxyl-modified silicone oil, polyether-modified oil, polyglycerol-modified silicone oil, dimethylpolysiloxane, dimethylsilicone, polyether-modified silicone, methylphenylsilicone, alkyl-modified silicone, higher fatty acid-modified silicone, methylhydrogen-containing silicone oil, fluorine-modified silicone, epoxy-modified silicone, carboxyl-modified silicone, methyl siliconeAlcohol-modified silicone, amino-modified silicone, methyl polysiloxane, methylphenyl polysiloxane, silicone resin, polydimethylsiloxane, polymethylhydrosiloxane, cyclic methyl polysiloxane, octamethyltrisiloxane, tetramethylhexasiloxane, high-polymerized methyl polysiloxane, and the like. The waxes are not particularly limited, and examples thereof include japanese lacquer wax (Japan wax), beeswax, sumac wax (sumac wax), lacquer wax (lacquer wax), sugar cane wax, palm wax, montan wax, carnauba wax, candelilla wax, rice bran wax, lanolin, spermaceti wax, reduced lanolin, liquid lanolin, hard lanolin, silosin (ceresin), and ozokerite (ozokerite). The steroid is not particularly limited, and examples thereof include cholesterol, dihydrocholesterol, and cholesterol fatty acid ester. The cationic polymer is not particularly limited, and examples thereof include cationic starch, cationic cellulose, cationic hydroxyethyl cellulose, cationic guar gum, cationic locust bean gum, cationic tamarind gum, cationic tara gum, cationic fenugreek gum, (N, N-dimethyl-3, 5-methylenepiperidinium chloride) -acrylamide copolymer, poly (N, N-dimethyl-3, 5-methylenepiperidinium chloride), polyethyleneimine, quaternized vinylpyrrolidone-aminoethyl methacrylate copolymer, adipic acid-dimethylaminoethoxypropylenediethylenetriamine copolymer, acrylamide- β -methacryloyloxyethyltrimethylammonium copolymer, and the like, examples of the viscosity modifier include, but are not particularly limited to, hydroxyethyl cellulose, hydroxypropyl methyl cellulose, dimethyldiallylammonium chloride-acrylamide copolymer, polyethylene glycol, high-polymer polyethylene glycol, polyvinyl alcohol, polyglutamic acid, carboxyvinyl polymer, acrylic acid-alkyl methacrylate copolymer, alkyl acrylate copolymer, and the like, and examples of the viscosity modifier include, but are not particularly limited to, alkyl alkanolamides such as coconut oil fatty acid monoethanolamide, coconut oil fatty acid diethanolamide, lauric acid diethanolamide, coconut oil fatty acid N-methyl ethanolamide, and the like; polyoxyethylene alkyl alkanolamides such as polyoxyethylene coconut oil fatty acid monoethanolamide; polyoxypropylene coconut oil fatPolyoxypropylene alkyl alkanolamides such as acid monoisopropanolamide; the water-soluble polymer, polysaccharide, cationic polymer, and the like are not particularly limited as the gloss imparting agent, and examples thereof include fatty acid ethylene glycol ester (ethylene glycol distearate, and the like), fatty acid polyethylene glycol ester, fatty acid monoethanolamide, and examples thereof include higher alcohols, such as cetyl alcohol, stearyl alcohol, and behenyl alcohol, and examples thereof include polyhydric alcohols, such as glycerin, 1, 3-butylene glycol, propylene glycol, dipropylene glycol, propylene glycol, sorbitol, diglycerin, triglycerol, and polyglycerin, and the like, and examples thereof include higher fatty acids, such as myristic acid, palmitic acid, stearic acid, and behenic acid, and examples thereof include amidoamines, such as stearic acid dimethylaminopropylamide, and hydrocarbons, examples of the wax include, but are not particularly limited to, liquid paraffin, polyisobutylene, squalane, etc., examples of the wax include, but are not particularly limited to, candelilla wax, carnauba wax, paraffin wax, microcrystalline wax, polyethylene wax, etc., examples of the ester include, but are not particularly limited to, animal and vegetable oils, isopropyl myristate, ethylhexyl palmitate, cetyl octanoate, cetyl ethylhexanoate, isononyl isononanoate, etc., examples of the silicone derivative include, but are not particularly limited to, dimethylpolysiloxane, methylphenylpolysiloxane, fatty acid-modified silicone, alcohol-modified silicone, amino-modified silicone, dimethiconol, etc., examples of the physiologically active ingredient include, but are not particularly limited to, natural plant extract ingredients that give any physiological activity to the skin when applied to the skin, vegetable extracts, waxes, esters, etc, The extract includes, but is not particularly limited to, extracts derived from plants, animals, and microorganisms, the antioxidant includes, but is not particularly limited to, tocopherols, dibutylhydroxytoluene, butylhydroxyanisole, gallic acid esters, and the metal ion chelating agent includes, but is not particularly limited to, 1-hydroxyethane-1, 1-diphosphonic acid, and 1-hydroxyethane-1, 1-diphosphonic acidPhosphonic acid tetrasodium salt, ethylenediaminetetraacetic acid and salts thereof (dipotassium dihydrate salt, disodium calcium salt, trisodium salt, tetrasodium dihydrate salt, tetrasodium tetrahydrate salt, and the like), hydroxyethylethylenediaminetriacetic acid and salts thereof, phosphoric acid and salts thereof, ascorbic acid and salts thereof, succinic acid and salts thereof, gluconic acid and salts thereof, polyphosphoric acid and salts thereof, metaphosphoric acid and salts thereof, tartaric acid and salts thereof, phytic acid and salts thereof, citric acid and salts thereof, maleic acid and salts thereof, polyacrylic acid and salts thereof, isopentene-maleic acid copolymer and salts thereof, silicic acid and salts thereof, hydroxybenzyliminodiacetic acid and salts thereof, iminodiacetic acid and salts thereof, diethylenetriaminepentaacetic acid and salts thereof, nitrilotriacetic acid and salts thereof, methylglycinediacetic acid and salts thereof, L-glutamic diacetic acid and salts thereof, L-aspartic diacetic acid and salts thereof, and the like, the preservative is not particularly limited, and examples thereof include parabens (methyl paraben, ethyl paraben, and butyl paraben), 1, 2-alkanediols (carbon chain length 6 to 14) and derivatives thereof, phenoxyethanol, isopropyl methylphenol, sodium benzoate, hinokitiol, and the like, the ultraviolet absorber is not particularly limited, and examples thereof include benzotriazoles, PABA-based, anthranilic acid-based, cinnamic acid-based, salicylic acid-based, benzophenone-based, and triazine-based, the perfume is not particularly limited, and examples thereof include extracts, essential oils, perfume resins, floral oils, and perfumes containing perfume components of natural substances such as combinations thereof, and the moisturizer is not particularly limited, and examples thereof include mucopolysaccharides, hyaluronic acid, chondroitin sulfate, and the like, Glutamic acid, chitosan and the like, and examples of the carbon include, but are not particularly limited to, carbon black, graphite, carbon fiber, activated carbon, bamboo charcoal, single-walled carbon nanotube, double-walled carbon nanotube, multi-walled carbon nanotube, carbon nanohorn, fullerene, carbon sphere and the like, and examples of the metal oxide include, but are not particularly limited to, silica, alumina (aluminumoxy), zirconia, titania, magnesia, Indium Tin Oxide (ITO), cobalt blue (CoO · Al), and the like₂O₃) Antimony oxide, zinc oxide, cesium oxide, zirconium oxide, yttrium oxide, tungsten oxide, vanadium oxide, oxygenCadmium oxide, tantalum oxide, niobium oxide, tin oxide, bismuth oxide, cerium oxide, copper oxide, iron oxide, indium oxide, boron oxide, calcium oxide, barium oxide, thorium oxide, indium tin oxide, magnesium silicate, ferrite, and the like, and salts thereof are not particularly limited, and examples thereof include salts of organic acids such as citric acid, malic acid, succinic acid, lactic acid, and salts of inorganic acids such as hydrochloric acid, sulfuric acid, nitric acid, carbonic acid, phosphoric acid, and the like, salts thereof include neutralizing agents and pH adjusting agents, and examples thereof include inorganic acids, organic acids, alkali metal salts, organic bases, and the like, and examples thereof include cleansing agents, and the like, and examples thereof include L-menthol, L-menthyl lactate, menthyl ether, menthanediol, camphor, peppermint, and the like, insect repellents include the like, and examples thereof include insect repellents, and the like, and enzymes, the dye is not particularly limited, and examples thereof include protease, cellulase, amylase, lipase, mannanase, etc., and examples thereof include Sudan red and D&C Red No17, D&C green No6, beta-carotene, soybean oil, Sudan brown, D&C yellow No11, D&C purple No2, D&C orange No5, quinoline yellow, annatto, and brominated acids, and the organic pigments are not particularly limited, and examples thereof include carbon black and D&The type C pigment, cochineal carmine or carmine (lakes) based on barium, strontium, calcium or aluminum, and the like, as the inorganic pigment, there are no particular restrictions, and examples thereof include anhydrous silicic acid, magnesium silicate, talc, kaolin, bentonite, mica, titanated mica, bismuth oxychloride, zirconium oxide, magnesium oxide, zinc oxide, titanium oxide, calcium carbonate, magnesium carbonate, yellow iron oxide, iron oxide red (colcothar), black iron oxide, ultramarine, chromium oxide hydrate, carbon black, calamine, and the like, as the pearl essence, there are no particular restrictions, and examples thereof include white pearl essence such as mica coated with titanium or bismuth oxychloride, colored pearl essence such as titanated mica coated with iron oxide, particularly, titanated mica coated with ferric blue (ferric blue) or chromium oxide, titanated mica coated with an organic pigment of the type described above, and the like, and pearls based on bismuth oxychloride, the pearling agent is not particularly limited, and examples thereof include ethylene glycol distearateExamples of the anti-inflammatory agent include, but are not particularly limited to, a fatty acid ester, mica, and the like, and examples of the anti-inflammatory agent include, but are not particularly limited to, tranexamic acid, thiotaurine, hypotaurine, and the like, and examples of the antioxidant include, but are not particularly limited to, glycyrrhizin, glycyrrhizates (e.g., dipotassium glycyrrhizinate and ammonium glycyrrhizinate), allantoin, thiotaurine, glutathione, catechin, albumin, ferritin, and metal thionine, and examples of the whitening agent include, but are not particularly limited to, salicylic acid derivatives such as L-ascorbic acid (vitamin C) and derivatives thereof, pantothenic acid derivatives, tranexamic acid and derivatives thereof, resorcinol derivatives, 4-methoxysalicylic acid potassium, and the like, other phenol derivatives, arbutin, placentin, plant extracts (e.g., chamomile extract, saxifrage extract, coix seed extract, and the like), the wrinkle-improving agent is not particularly limited, and examples thereof include retinol, retinal, retinoic acid, isotretinoin, tocopherol retinoic acid ester, retinol palmitate, retinol acetate, benzyl ursolate, phosphoric ursolate, benzyl betulinate, phosphoric acid benzilate, sodium chondroitin sulfate, 2-methacryloyloxyethyl phosphorylcholine, swertia japonica extract, zingiber officinale roscoe leaf extract, Codonopsis lanceolata root extract, cornflower extract, and other various extracts, and the vitamins include, but are not particularly limited to, vitamin a and derivatives thereof; vitamin B6 derivatives such as vitamin B6 and vitamin B6 hydrochloride; nicotinic acid, nicotinic acid derivatives of nicotinic acid amide; vitamin E and its derivatives; beta-carotene, etc., as amino acids, there are no particular restrictions, for example, hydroxyproline, l-serine, trimethylglycine, l-arginine, etc., as hair growth agents, there are no particular restrictions, for example, pantothenic acid ethyl ether, adenosine, beta-glycyrrhetinic acid, minoxidil, etc., as antibacterial agents, there are no particular restrictions, for example, resorcinol, sulfur, salicylic acid, etc., as hormonal agents, there are no particular restrictions, for example, oxytocin, adrenocorticotropic hormone, vasopressin, secretin, gastrin, calcitonin, hinokitiol, ethinylestradiol, etc., as plant extracts, there are no particular restrictions, for example, phellodendron bark, etc., as well as phellodendron bark, etc., as plant extracts, there are no particular restrictions, for exampleThe active agent is not particularly limited, and examples thereof include royal jelly, photosensitizer, cholesterol derivative, etc., the blood circulation promoter is not particularly limited, and examples thereof include capsaicin, zingerone, cantharides, garcinia, orange peel, angelica sinensis, seaweed, etc., the metal ion chelating agent is not particularly limited, and examples thereof include 1-hydroxyethane-1, examples of the organically modified clay mineral include, but are not limited to, 1-diphosphonic acid, 1-hydroxyethane-1, 1-diphosphonic acid tetrasodium salt, edetate disodium, edetate trisodium, edetate tetrasodium, sodium citrate, sodium polyphosphate, sodium metaphosphate, gluconic acid, phosphoric acid, citric acid, ascorbic acid, succinic acid, edetic acid, and ethylenediamine hydroxyethyltriacetic acid trisodium, and the organically modified clay mineral includes, for example, clay minerals such as montmorillonite (hectorite, bentonite, and montmorillonite), kaolinite, illite, marine clay minerals (sea mud), desert rose clay minerals, and pascaite (pascaite) modified with a quaternary amine group and a carboxyl group.

When the skin care composition of the present invention is prepared into an emulsion containing a surfactant and an oil agent, the oil agent is not particularly limited in terms of spreadability, stickiness, moisturizing feel, sustained moisturizing feel, skin compatibility, and skin elasticity when applied to the skin, and for example, hydrocarbons are preferably used, more preferably mineral oil, and still more preferably liquid paraffin or silosin (ceresin).

The content of the skin care agent of the present invention in the skin care composition of the present invention is not particularly limited, and from the viewpoint of the effect of the present invention, the content of the organic ammonium salt in terms of an anhydrate is preferably 0.001% by mass or more, more preferably 0.01% by mass or more, further preferably 0.1% by mass or more, particularly preferably 1.0% by mass or more, and particularly preferably 10.0% by mass or more.

The skin care composition of the present invention can be produced by diluting the skin care agent of the present invention in a solvent in such a manner that the content of the skin care agent is within the above range, for example. The solvent is not particularly limited, and examples thereof include water; alcohols such as ethanol, 1-propanol, 2-propanol, 1-butanol, benzyl alcohol, hexenol, nonenal, and methyldecenol; alkyl ethers such as diethylene glycol monomethyl ether and diethylene glycol dimethyl ether, and polyhydric alcohols such as glycerin, diglycerin, 1, 3-butylene glycol, propylene glycol, dipropylene glycol, isoprene glycol, propylene glycol, sorbitol, and maltitol. These may be used alone or in combination of 2 or more. Among them, water or an aqueous solution is preferable, and water such as purified water is particularly preferable.

The skin care composition of the present invention can be produced by, for example, adding the skin care agent of the present invention and the other components to a solvent and mixing them. Heating to dissolve the solid raw materials, mixing, stirring and uniformly mixing according to requirements.

The skin care composition of the present invention may be prepared by using not only the organic ammonium salt but also the cation and anion constituting the organic ammonium salt, by preparing the organic ammonium salt used in the present invention in advance and mixing the organic ammonium salt with water, a solvent and other components to prepare the skin care composition, or by mixing the amine compound and the acidic compound, which are raw materials for the cation and anion constituting the organic ammonium salt, with water, a solvent and other components in any order without limitation.

The skin care composition of the present invention can impart a moisturizing feeling when applied to the skin or the like, and can give a good touch without stickiness, due to the short-term and long-term moisturizing or electrification preventing (antistatic) effects caused by the non-volatility of the organic ammonium salt of the present invention contained therein. Further, the organic ammonium salt has safety, affinity for skin and the like, permeability, low irritation, and whitening effect, and thus a skin care composition having high safety, good skin compatibility and skin elasticity, and low irritation to skin and the like can be obtained. The ammonium salt is also useful as a base material for a skin care composition in that the solubility of the active ingredient is high, and has excellent permeability into the skin and the like, and therefore, the ammonium salt has excellent water-retaining and moisture-retaining effects on the skin and the like, and can be used as a carrier for the active ingredient. In addition to skin application, the composition can be applied to keratin, nails, oral cavity, and nasal cavity, which are required to have the effects of the present invention.

Examples

The present invention will be described in further detail with reference to examples, but the present invention is not limited to these examples.

[1] Evaluation of cosmetic compounding Agents

(Compound (I))

Compounds A1-A54

The compounds a1 to a54 shown in tables 1 to 8 were synthesized by the following method.

Compounds a 1-a 51: synthesized by the method described in Japanese patent application laid-open No. 2014-131974.

Compound a 52: a reagent (glycerol) manufactured by Wako pure chemical industries, Ltd.

Compound a 53: ion-exchanged water is used.

Compound a 54: a reagent (tetrabutylammonium bromide) manufactured by Wako pure chemical industries, Ltd. was used.

1. State (appearance) of cosmetic compounding ingredients

Organic ammonium salts were synthesized at the molar ratios of anion to cation shown in tables 1A to 1C, and the state under 25 ℃ was confirmed.

2. Evaluation of solubility of active ingredient

The solubility of the active ingredients in 20 wt% aqueous solutions of the cosmetic compounding agents of examples a52 to a92 and comparative examples a1 and a2 described in tables 2A to 2C was evaluated. As the active ingredient, gallic acid and glutamic acid with insoluble antioxidant effect and moisturizing effect are used. The solubility of glutamic acid in comparative examples A1 (glycerin 20 wt% aqueous solution), A2 (ion-exchanged water) was less than 1 wt%, and the examples all had high solubility. In addition, gallic acid also has the same tendency, and can dissolve more effective components. Thus, the cosmetic compounding agent of the present invention can be used as a base, a solvent, a carrier, and the like of cosmetics.

3. Influence of the molar ratio of organic ammonium salt cation and anion on the solubility of the active ingredient

The solubility of the active ingredients was evaluated using examples A93 to A99 and comparative example A3 prepared by mixing ammonium salts or a composition of ammonium salts and acids and/or bases at the mixing ratio shown in Table 3 to give 20 wt%. As the active ingredient, gallic acid and glutamic acid with insoluble antioxidant effect and moisturizing effect are used. Method a for producing a test sample was carried out using an acid: lactic acid and base: after synthesizing an organic ammonium salt from 2-amino-2-hydroxymethyl-1, 3-propanediol (tromethamine), ion-exchanged water is added to produce an organic ammonium salt aqueous solution, and an active ingredient is added. The production method B is to add an acid: lactic acid and base: the preparation method C comprises adding acid: lactic acid, alkali: tromethamine and active ingredients.Furthermore, by¹H-NMR confirmed that the ammonium salt was formed by any of the production methods.

As a result of examining the influence of the molar ratio of the starting material tromethamine to lactic acid on the solubility of compound a5, examples a93 to a99 showed that the solubility of gallic acid was improved and the solubility was equal to or higher than that of glutamic acid, as compared with the case where only lactic acid was used in the test as a comparative example, and it was confirmed that the solubility was improved by using an organic ammonium salt. However, as in examples a93, a94 and a95, the molar ratio of the anion to the cation was 1: solubility is particularly excellent when the presence ratio of 1 mole (1: 1 molar ratio of acid to base) of ammonium salt is high. In addition, it can be confirmed from examples a93 and a95 that, independently of the production method, the molar ratio of acid to base is 1: 1 mol, the solubility is the same.

From the results in table 3, the molar ratio of acid to base of the cosmetic compounding agent including the hair treatment agent and the skin care agent is preferably 1: 1 mol-2: 1 mol, in particular, from the solubility of glutamic acid (3g/100g or more), gallic acid (4g/100g or more), 1: the solubility of 1 mole was excellent. In addition, the molar ratio of acid to base was 1: 2, pH8.4, and the molar ratio of acid to base is 1: at pH5, pH 9.1. For safety-related pH, the molar ratio was 2: 1-1: when 5, the pH value is preferably 3-10, 1: 2-1: 1, more preferably the pH value is 5-9, and the molar ratio is 1: when 1, the pH is more preferably 6-8.

This suggests that the cosmetic compounding agent of the present invention has an organic ammonium salt structure, and therefore has excellent solubility of the active ingredient, and particularly, has excellent solubility of an organic ammonium salt having an equimolar amount of cation to anionic carboxylic acid.

TABLE 3

4. Dispersibility test of Metal oxide

The dispersibility of the metal oxide used in the cosmetic in the carbon-based material was confirmed. In addition, the samples of tables 4-8 were produced using the production method B described above.

The compounds of the examples and comparative examples shown in Table 4 were visually observed to be dispersed in 0.25g of each compound, 0.50g of ion-exchanged water, and 0.10g of zirconium oxide (IV) (Wako pure chemical industries, Ltd.) mixed at 2000rpm for 1 min.times.5 times by a rotary-revolution mixer (Nippon Co., Ltd. (シンキー, ARE-310)). The condition of the zirconia dispersed was evaluated as "good", and the condition of the zirconia not dispersed but sedimented was evaluated as "x". The results are shown in Table 4.

The compounds of the examples all dispersed zirconia well to give a dispersion. On the other hand, with the compound of comparative example a4, zirconia precipitated immediately without dispersion.

TABLE 4

The zirconium oxide was evaluated by titanium (IV) oxide (Wako pure chemical industries, Ltd.) by the same charge amount and operation as described above (Table 5).

The compounds of the examples all dispersed titanium oxide well to obtain a dispersion. On the other hand, with the compound of comparative example A5, titanium oxide settled and the dispersibility was low.

That is, it is considered that the cosmetic compounding agent of the present invention utilizes the structural feature of the cation composed of the hydroxyl group having a large number of hydrogen-bonding functional groups (having hydrogen-bonding donating property and coordination property), and the affinity with the oxygen atom of the hydrogen-bond accepting titanium oxide is high, and the affinity of the hydroxyl group of the quaternary ammonium salt with the metal atoms of the coordinating zirconium oxide and titanium oxide makes the titanium oxide well dispersed.

From the results, it is suggested that the organic ammonium salt of the present invention has excellent affinity with inorganic materials such as metals and metal oxides having a hydrogen bond accepting functional group, and is useful as a cosmetic compounding agent.

TABLE 5

5. Redispersibility

The dispersion liquids of zirconia and titania obtained in tables 4 and 5 were dehydrated under reduced pressure at 50 ℃ for 3 hours to obtain compounds in a dry state. Then, 0.50g of ion-exchanged water was added to the samples of zirconia and titania, and the dispersion state was visually observed after mixing the samples at 2000rpm for 1min × 5 times by a revolution and rotation mixer (nippon japanese unexamined patent publication (kokai) No. シンキー), ARE 310. As a result, the example compounds were well dispersed, and a uniform dispersion liquid was obtained. On the other hand, the compounds of the comparative examples were mixed by a mixer, and immediately, a precipitate was observed (Table 6).

From the results, it was confirmed that the organic ammonium salt of the present invention was not volatilized, and that the compound after dispersion was dried and then dispersed again, the compound was well dispersed. In addition, in addition to the dispersion method of the system in which the metal oxide is added to the aqueous solution of the organic ammonium salt of the present invention to disperse the metal oxide, it is suggested that the material having a hydrogen bond accepting functional group contained in the cosmetic compounding agent can be redispersed and is useful in the use of the cosmetic compounding agent because the metal oxide is dispersed well in the system in which the metal oxide is dispersed in the form of powder by adding water.

TABLE 6

6. Metal oxide Dispersion test 2

The compounds of the examples and comparative examples shown in table 7 were visually observed to be dispersed in 0.25g of each compound, 0.50g of ion-exchanged water, and 0.10g of zinc oxide (Shidai industries, Ltd.) mixed at 2000rpm for 1min × 5 times by a rotary-revolution mixer (Japanese Nissan Kabushiki Kaisha (Ltd.) ((シンキー), ARE-310). The state of zinc oxide dispersed was evaluated as "O", and the state of zinc oxide not dispersed but sedimented was evaluated as "X". The results are shown in Table 7.

The compounds of the examples all dispersed zinc oxide well to give a dispersion. On the other hand, with the compound of comparative example a7, zinc oxide precipitated immediately without dispersion.

That is, it is considered that the cosmetic compounding agent of the present invention utilizes the structural feature of a cation composed of a hydroxyl group having a large number of hydrogen-bonding functional groups (having hydrogen-bonding donating properties and coordinating properties), and the affinity with the oxygen atom of the hydrogen-bond accepting zinc oxide is high, and the affinity of the hydroxyl group of the quaternary ammonium salt with the metal atom of the complex zinc oxide makes the zinc oxide well dispersed.

TABLE 7

7. Carbon (carbon nanotube) dispersibility test

The compounds of the examples and comparative examples shown in Table 8 were visually observed to be dispersed in 0.25g of each compound, 0.75g of ion-exchanged water, and 0.025g of carbon-based carbon nanotubes (multi-layer, 3 to 20nm) (Wako pure chemical industries, Ltd.) mixed at 2000rpm for 1 min.times and 5 times by a rotary-revolution mixer (Nippon Kogyo Co., Ltd. (シンキー, ARE-310)). The state in which the carbon nanotubes were dispersed was evaluated as "o", and the state in which the carbon nanotubes were not dispersed but sedimented was evaluated as "x". The results are shown in Table 8.

As a result, the compounds of the examples dispersed carbon nanotubes well, and a low viscosity dispersion liquid that worked well was obtained. On the other hand, with the compound of comparative example A8, the carbon nanotubes settled and did not disperse.

That is, it is considered that the cosmetic compounding agent of the present invention has good affinity with carbon by utilizing the structural characteristics of the cationic species composed of a hydroxyl group having a large number of hydrogen-bonding functional groups (having hydrogen-bonding donating properties and coordinating properties), and the carbon nanotube having this hydrogen-bonding accepting property has high affinity with a carbon-carbon unsaturated bond (pi-electron system), and thus the carbon nanotube is well dispersed.

From the results, it is suggested that the organic ammonium salt of the present invention is excellent in affinity with carbon-based compounds, and is useful as a cosmetic compounding agent using such a material.

TABLE 8

[2] Evaluation of Hair treatment agent

Hydrates of compounds B1 to B29 shown in tables 9 to 21 were synthesized by the following method.

Compounds B1-B4: synthesized by the method described in Japanese patent laid-open No. 2014-131975.

Compounds B5-B22: synthesized by the method described in Japanese patent application laid-open No. 2014-131974.

Compound B23: synthesized by the method described in Japanese patent laid-open No. 2012-031137.

Compound B24: tetrabutylammonium bromide was used as a reagent produced by Kanto chemical Co.

Compound B25: 1-butyl-3-methylimidazolium chloride (BMI-Cl) was obtained using a reagent manufactured by Tokyo chemical industry Co.

Compound B26: glycerol was obtained from Wako pure chemical industries, Ltd.

Compound B27: ion-exchanged water is used.

Compound B28: sodium lactate was prepared using a reagent manufactured by Kanto chemical Co.

Compound B29: 2-amino-2-hydroxymethyl-1, 3-propanediol hydrochloride (trihydrochloride) was synthesized by the method described in Japanese patent application laid-open No. 2014-131974.

Compound B30: 2-amino-2-hydroxymethyl-1, 3-propanediol oleate is synthesized by the method described in Japanese patent application laid-open No. 2014-131974.

Compound B31: 2-amino-2-hydroxymethyl-1, 3-propanediol linoleate was synthesized by the method described in Japanese patent application laid-open No. 2014-131974.

Compound B32: 2-amino-2-hydroxymethyl-1, 3-propanediol isostearate, compound B33: 2-amino-2-methyl-1, 3-propanediol oleate, compound B34: 2-amino-2-methyl-1, 3-propanediol linoleate, compound B35: 2-amino-2-methyl-1, 3-propanediol isostearate was synthesized by the method described in Japanese patent application laid-open No. 2014-131974.

For the evaluation below, human hair black hair manufactured by the company of Borago, Japan (Kokai) ビューラックス was used as the healthy hair. Damaged hair is produced by repeating three perming treatments and bleaching treatments for healthy hair.

1. Water-Retention/adhesion to Hair of Hair treatment agent

1-1 Water Retention/adhesion to healthy Hair Using organic ammonium salt

An 80 wt% aqueous solution of the compounds B1 to B26 (the content of the compounds B1 to B23 was converted to an anhydride) was prepared, and the water content was 20.0 wt% as determined by Karl Fischer-Tropsch water content meter (KF-200, manufactured by Mitsubishi chemical analysis science and technology). Healthy hair used was healthy hair without chemical treatment (black hair of human hair, manufactured by bolasuss corporation, japan, ltd. ビューラックス). The moisture content of the hair was measured by an infrared moisture meter (manufactured by Katy chemical research institute, Inc. (ケット chemical research institute)) to obtain a pre-test moisture content A.

0.05g of hair (weight of hair A before test) was immersed in 3.0g of 80 wt% aqueous solutions of compounds B1 to B26, respectively, for 60 minutes. After dipping, the hair was removed, the compound was wiped off with a paper towel (KimWipes) until the weight change disappeared, and the weight was measured (hair weight B after the test). And standing the wiped hair in a constant temperature and humidity apparatus with the temperature set to 40 ℃ and the RH set to 35-40%. The moisture content after 24 hours (moisture content after the test B) was measured, and the moisture reduction rate was calculated by the following formula. Similarly, the same evaluation was carried out using only ion-exchanged water without using an 80 wt% aqueous solution (comparative example B4).

Water reduction rate (%) [ (water fraction before test a-water fraction after test B)/water fraction before test a ] × 100

The adhesion rate of the compound to hair was calculated using the following formula.

Compound adhesion rate (%) (after-test hair weight b (g) — pre-test hair weight a (g)/(g))

From the results of table 9, it was confirmed that the healthy hairs treated with the compounds B1 to B23 of the examples had a smaller water content reduction rate and were more excellent in water retentivity than the healthy hairs treated with the compounds B24 to B27 of the comparative examples. In addition, in the measurement of the hair adhesion ratio based on the change in weight, the adhesion of the ion-exchanged water of comparative example B4 was not observed, and the adhesion ratios of the compounds B24, B25, and B26 of comparative examples B1, B2, and B3 were 1.0%, respectively, whereas the adhesion ratios of the compounds of the examples were 1.1 to 9.4%, respectively, and it was confirmed that the adhesion to hair was excellent, and the advantages of the hydrogen bond functional group of the organic ammonium salt, the water retentivity of the cationic structure, and the adhesion to hair were exhibited. Further, compound B11, which was a liquid having the same cation at 25 ℃, had a smaller water content decrease rate and a larger adhesion rate than compound B12, which was a solid, and was a liquid compound having excellent water retentivity and adhesion at 25 ℃. Further, compound B3 having the same anion has a smaller moisture reduction rate and a larger adhesion rate than compound B23, and therefore, the water retentivity and adhesion of the cation composed only of a hydrogen bonding functional group having no alkyl group in the ammonium cation are excellent. Further, compounds B6 and B11 having the same anion have a smaller moisture reduction rate and a larger adhesion rate than compound B9, and therefore, have a hydrogen-bonding functional group in R¹In the structure (2), the compound composed of only hydrogen-bonding functional groups in which all the terminals are hydroxyl groups is excellent in water retentivity and adhesiveness.

These results suggest that the hair treatment agent containing an organic ammonium salt of the present invention has excellent adhesion to healthy hair, and thus can maintain the moisture retention of healthy hair for a long period of time. In addition, it was also shown that the effect of the compound which was liquid at 25 ℃ was high.

1-2 Water Retention/adhesion to damaged wool Using organic ammonium salt

An 80 wt% aqueous solution of compounds B1 to B4, B6, B7, B9 to B13, and B23 to B26 (in terms of anhydrous content in compounds B1 to B4, B6, B7, B9 to B13, and B23) was prepared, and the water content was confirmed to be 20.0 wt% by karl fischer moisture meter. The damaged hair was produced by the following method.

< production of damaged Hair >

As the permanent wave treatment, the hair was immersed in a 6.5% ammonium thioglycolate aqueous solution (ph9.5) for 10 minutes, then immersed in a 6% sodium bromate aqueous solution (ph6.5) for 10 minutes, rinsed, dried with a hair dryer, and combed 100 times. Then, as a bleaching treatment, the bleaching treatment was performed in a 1: 1 for 30 minutes, rinsed, dried with a hair dryer, and combed 100 times. The permanent wave treatment and the bleaching treatment were repeated three times to produce damaged hair.

The water content reduction rate, hair adhesion rate, and compound adhesion rate were determined by the same methods as in 1-1, using only the above sample and ion-exchanged water (comparative example B8).

From the results in table 10, it was confirmed that the damaged wool treated with the compounds B1 to B4, B6, B7, B9 to B13, and B23 of the examples had a smaller water reduction ratio and was more excellent in water retentivity than the damaged wool treated with the compounds B24 to B27 of the comparative examples. The adhesion rate to hair was not observed in the ion-exchanged water of comparative example B8, but was 0.9 to 1.2% in comparative examples B5 to B7, whereas the adhesion rate of the compound of the examples was 1.4 to 2.8%, indicating excellent adhesion to hair.

In addition, for healthy hair and damaged hair, adhesion to healthy hair was confirmed by the same method as described above using 2-amino-2-hydroxymethyl-1, 3-propanediol oleate (compound B30), 2-amino-2-hydroxymethyl-1, 3-propanediol linoleate (compound B31), 2-amino-2-hydroxymethyl-1, 3-propanediol isostearate (compound B32), 2-amino-2-methyl-1, 3-propanediol oleate (compound B33), 2-amino-2-methyl-1, 3-propanediol linoleate (compound B34), and 2-amino-2-methyl-1, 3-propanediol isostearate (compound B35) of the present invention, as a result, the adhesive properties were higher than those of the compounds of comparative examples B1 to B8. The evaluation of the moisture barrier property of hair by the method described in [3] evaluation of skin care agent (4) moisture blocking property test for compound B31 (example) suggests that the moisture evaporation suppression rate was 48.1%, which was higher than the moisture evaporation suppression rates of comparative examples C16 to 18, and the moisture barrier property of hair was excellent.

1-3 influence of the molar ratio of cation and anion of organic ammonium salt on Water Retention

The moisture reduction rate, hair attachment rate, and compound attachment rate of healthy hair and damaged hair were measured using examples B36 to B43, comparative example B9, and comparative example B10, which were prepared as compositions of ammonium salts shown in table 11 or ammonium salts and acids and/or bases at a mixing ratio of 50 wt%. The damaged hair was produced by the method described in 1-2. The water content reduction rate, hair adhesion rate, and compound adhesion rate were determined by the same methods as those described in section 1-1. Method a for producing a test sample was carried out by acid: lactic acid and base: in the method B, after synthesizing an organic ammonium salt from tromethamine, ion-exchanged water is added to produce an organic ammonium salt aqueous solution, and an acid: lactic acid and base: tromethamine and production thereof¹H-NMR confirmed formation of ammonium salt). The samples in tables 9, 10, 12 to 17 and 21 were produced by production method B except for compound B23.

TABLE 11

From the results in table 11, it was confirmed that the healthy hairs and damaged hairs treated in examples B36 to B43 had a smaller water content reduction rate and an excellent water retentivity for the healthy hairs and damaged hairs than the healthy hairs and damaged hairs treated in the comparative examples. The hair adhesion rate was not observed with the ion-exchanged water of comparative example B10, while the adhesion rate to healthy hair and damaged hair was 1.1% for lactic acid of comparative example B9, whereas the adhesion rate to healthy hair was 1.7 to 2.8% and the adhesion rate to damaged hair was 1.6 to 2.8% in the examples, showing excellent adhesion to healthy hair and damaged hair.

As a result of examining the influence of the molar ratio of 2-amino-2-hydroxymethyl-1, 3-propanediol (tromethamine) and lactic acid as raw materials on the water retentivity of healthy and damaged hair with respect to compound B11, the water retentivity of examples B36 to B43 was improved and the water retentivity effect of the organic ammonium salt was confirmed, as compared with the case where the test was carried out using only lactic acid as a comparative example. From the viewpoint of adhesion to hair, the mixing ratio of the acid and the base is preferably 1: 5-5: 1 mol. In particular, when the molar ratio of anion to cation is 1: in the case of 1 mole, it was confirmed that the adhesiveness was excellent, the water content reduction rate was the lowest, and the water retentivity was particularly excellent. In addition, compared to examples B36 and B37, it was confirmed that, regardless of the production method, as long as the molar ratio of anion to cation was 1: 1 mol, and has the same water retention effect.

Thus, it is suggested that the hair treatment agent of the present invention has an organic ammonium salt structure and thus has excellent water retentivity, and particularly, excellent water retentivity with respect to the organic ammonium salt having an equimolar amount of cation to anionic carboxylic acid.

1-4 measurement of surface resistance of organic ammonium salt

0.7g of each of the compounds B11 and B26 (in terms of the content of anhydride) was applied to an artificial leather made of polyurethane, and the surface resistance value was measured using a high resistance meter (Stack TR-2, manufactured by Tokyo electronic Co., Ltd.). Greater than 4X 10 in a state where nothing is applied¹¹Omega, on the other hand, all were liquid at the time of measurement, and Compound B11 was less than 1X 10⁸Omega, Compound B26 is 5X 10⁸Therefore, compound B11 has better conductivity on the coated surface, suppresses static electricity, has an antistatic effect, and exhibits superiority in structural features of the hair treatment agent of the present invention, compared with compound B26.

Further, when 0.7g (in terms of anhydrous content) of compound B28 (sodium lactate) was applied to the polyurethane artificial leather, and the resultant was dried to evaporate water, the applied surface became solid, and the surface resistance value measured in the same manner as described above was 2 × 10⁸Omega, therefore, Compound B11 (less than 1X 10) was confirmed⁸Ω) non-volatility, and liquid properties at 25 ℃ (can be uniformly applied to a coated material).

This suggests that the hair treatment agent of the present invention is excellent in antistatic properties and contributes to sensory properties such as hair coagulation.

2. Use of hair treatment agent for healthy hair and damaged hair

Sensory evaluation of healthy Hair Using organic ammonium salt

An 80 wt% aqueous solution of compounds B11, B12, B23, B26 and B27 (in terms of the content of anhydride in compounds B11, B12 and B23) was prepared as a sample. A10.0 g sample was uniformly applied to a bundle of about 10g healthy hairs using a brush for 1 minute and left to stand for 5 minutes. After leaving for 5 minutes, the plate was rinsed with hot water at 40 ℃ for 30 seconds, and finger combing at the time of rinsing was evaluated. The rinsed tufts were towel-dried and air-dried for 1 day, and the superiority and inferiority of the test tufts to the uncoated specimens were evaluated for the items of softness, finger combing property, hand touch, elasticity and toughness (bare-handed touch), thickness (visual observation), cohesiveness, moist touch, surface smoothness, non-stickiness (bare-handed touch), and gloss (visual observation).

The evaluation was made in the following 4 grades.

Very good: is excellent.

O: is good.

And (delta): there was no change.

X: it is not good.

TABLE 12

According to table 12, the finger combing properties at the time of washing of the compounds B11, B12, and compound B23 of the examples were excellent as compared with the comparative examples. In addition, even after air-drying, the compounds of examples showed good effects in all items evaluated, compared to the comparative examples. From the results, it was confirmed that the compound having a salt structure of cation and anion as in the examples exhibits a good effect as a hair treatment agent. Further, the compounds B11 and B23 of the examples were superior to the compound B12 in flexibility, finger combing property, hand touch, cohesiveness, moist feeling, gloss, smoothness of the surface, and non-stickiness. From these results, it was confirmed that the quaternary ammonium salt was liquid and that the effective component was not precipitated when water used as a solvent was evaporated, and thus the quaternary ammonium salt was excellent in various sensory evaluations. In particular, since the compound B11 composed of only a hydrogen-bonding functional group can fix the product of the present invention to hair well for a long time as compared with the compound B23 containing an alkyl group in the quaternary ammonium salt cation, the compound B11 shows a good result in the evaluation of the thickening, and the cation can be selected and evaluated in accordance with the thickening requirement.

In addition, healthy hair was subjected to sensory evaluation by the same method as described above using 2-amino-2-hydroxymethyl-1, 3-propanediol oleate (compound B30), 2-amino-2-hydroxymethyl-1, 3-propanediol linoleate (compound B31), 2-amino-2-hydroxymethyl-1, 3-propanediol isostearate (compound B32), 2-amino-2-methyl-1, 3-propanediol oleate (compound B33), 2-amino-2-methyl-1, 3-propanediol linoleate (compound B34), 2-amino-2-methyl-1, 3-propanediol isostearate (compound B35) of the present invention, as a result, the evaluation was made that the composition was superior in flexibility, finger combing property, hand touch feeling, elasticity, toughness, thickening property, cohesiveness, moist feeling, smoothness of surface, non-stickiness, and gloss to the compounds of comparative examples.

From these results, it is suggested that the hair treatment agent of the present invention can provide softness, finger combing property, hand touch, elasticity and toughness, thickening property, cohesiveness, moist feeling, smooth surface, non-stickiness, excellent gloss, good touch and appearance after rinsing hair.

Sensory evaluation of damaged Hair Using organic ammonium salt

An 80 wt% aqueous solution of compounds B11, B12, B23, B26 and B27 (in terms of the content of anhydride in compounds B11, B12 and B23) was prepared as a sample. A10.0 g sample was uniformly applied to about 10g of the damaged hair bundle for 1 minute using a brush, and left to stand for 5 minutes. After leaving for 5 minutes, the plate was rinsed with hot water at 40 ℃ for 30 seconds, and finger combing at the time of rinsing was evaluated. The rinsed bundles were dried with a towel and then air-dried for 1 day, and the advantages and disadvantages of the test bundles with respect to the uncoated sample were evaluated with respect to the items of elasticity, toughness (bare-handed touch), cohesiveness, smoothness of the surface, and no wavy form.

The evaluation was made in the following 4 grades.

Very good: is excellent.

O: is good.

And (delta): there was no change.

X: it is not good.

Watch 13

From table 13, it was confirmed that the compounds B11, B12, and B23 of the examples were more excellent in evaluation of finger combing property at the time of washing, elasticity and toughness after air-drying, cohesiveness, smoothness of the surface, and no wavy form than the comparative examples, and had higher effect of treating damaged hair than the comparative examples. From the results, it was confirmed that the compound having a salt structure of cation and anion as in the examples exhibits a good effect as a hair treatment agent.

Further, the compounds B11 and B23 of the examples were excellent in elasticity and toughness as compared with the compound B12. From the results, it is suggested that the quaternary ammonium salt is liquid, does not volatilize, is uniformly coated on the surface, and further penetrates into the inside.

In addition, using the 2-amino-2-hydroxymethyl-1, 3-propanediol oleate (compound B30), 2-amino-2-hydroxymethyl-1, 3-propanediol linoleate (compound B31), 2-amino-2-hydroxymethyl-1, 3-propanediol isostearate (compound B32), 2-amino-2-methyl-1, 3-propanediol oleate (compound B33), 2-amino-2-methyl-1, 3-propanediol linoleate (compound B34), 2-amino-2-methyl-1, 3-propanediol isostearate (compound B35) of the present invention, sensory evaluation was made on damaged hair by the same method as described above, as a result, it was evaluated that the composition was superior in elasticity, toughness, cohesiveness, smoothness of the surface, suppression of waviness, and had good touch and appearance, as compared with the compounds of comparative examples.

From these results, it is suggested that the hair treatment agent of the present invention can provide elasticity, toughness and cohesiveness after rinsing hair even in damaged hair, has a smooth surface, is excellent in suppression of waving, and has good touch and appearance.

3. Use of hair treatment composition in healthy and damaged hair

3-1 sensory evaluation of healthy Hair Using shampoo Agents blended with organic ammonium salt

Production of Hair treatment composition (shampoo)

As an example of a hair treatment composition using the hair treatment agent of the present invention, the following shampoo preparations were produced.

0.5 mass% of cationized hydroxyethylcellulose (made by Toho chemical industry Co., Ltd., Catinal HC-200) and purified water were uniformly mixed at 70 to 80 ℃, POE (3) sodium lauryl ether sulfate (made by Sanji grease Co., Ltd., Spamin SA) was added to make it 11.25 mass% (active ingredient), coconut oil fatty acid amide propyl betaine (made by Sanji grease Co., Ltd., ミヨシ grease Co., Ltd., AMPHOREX CB-1) was added to make it 3.75 mass% (active ingredient), then compound B11 was added to make it 0.5, 3.0, and 10.0 mass%, compound B7, B23, B26, B27, and B28 were added to make it 3.0 mass% (in terms of anhydrous content with respect to compounds B7, B11, and B23), and the mixture was uniformly mixed at 70 to 80 ℃ for 20 to 20 minutes. Subsequently, the mixture was cooled to 30 ℃ or lower, and purified water corresponding to the evaporation part was added so that the total amount of the hair treatment composition became 100 mass%, and the mixture was uniformly mixed to produce a hair treatment composition. For the pH of the hair treatment composition, citric acid or sodium hydroxide is added to make pH 6.0.

Evaluation of repeated treatments with healthy wool

About 5g of healthy hair was immersed in 350ml of a 7-fold diluted aqueous solution of each of the hair treatment compositions (shampoo agents) at 35 to 40 ℃ to wash the hair. Rinsing with 500ml of warm water at 35-40 ℃ for 5 times, drying at 80 ℃ and then air-drying at 25 ℃. The series of treatments of shampooing, rinsing and drying was repeated 10 times to evaluate the aggregation of the air-dried hair, the moist feeling of the hair, the luster of the hair, the smoothness of the hair surface and the non-stickiness of the hair surface.

The evaluation was made in the following 4 grades.

Very good: is excellent.

O: is good.

And (delta): it is slightly poor.

X: it is not good.

The surface of the air-dried hair was observed with a Scanning Electron Microscope (SEM) (JCM-5000, manufactured by Nippon electronics Co., Ltd.). Fig. 1 shows a photograph of the appearance of hair after air drying and an SEM photograph of the surface of hair.

TABLE 14

According to table 14, the hair of the healthy hair of examples B50 to B52 treated with the shampoo agent containing 3.0 mass% of the compounds B11, B23, and B7 had good aggregation, moist feeling, and luster, and the hair surface was not sticky and had good smoothness. The treated healthy hair had no aggregation in the comparative examples, and the hair was loose, but the hair had good aggregation in the examples. From the results of SEM observation, it was confirmed that the hair of examples B50 to B52 had smooth hair surfaces and no cuticle peeling (FIG. 1). The evaluation results were good for both the healthy hairs of examples B53 and B54 treated with the shampoo solutions containing 0.5 and 10 mass% of compound B11. On the other hand, the evaluation results of the hair of comparative example B16 treated with the shampoo agent containing compound B27 (ion-exchanged water) were both poor, and comparative examples B15 and B17 using compound B26 (glycerin) and compound B28 (sodium lactate) tended to be inferior to examples B50 to B52 in both evaluations.

It was confirmed that the compound having a salt structure of cation and anion as in examples exhibited a good effect as a shampoo agent. Further, the compounds of examples were more excellent in sensory evaluation than compound B28 (sodium lactate), and therefore, it was suggested that the effect of the organic ammonium salt having a hydrogen-bonding functional group in the cation and anion and being liquid at 25 ℃ was high.

Further, by blending the compounds of examples with a shampoo agent, the items of moist feel, gloss and smoothness were very excellent as compared with the results in table 12, and therefore, the product of the present invention exhibited a higher treatment effect by interacting with the shampoo agent.

From the results, it is suggested that the hair treatment composition using the hair treatment agent of the present invention can impart cohesiveness, a moist feeling, luster, and smoothness to hair and can give a good touch without stickiness.

3-2 sensory evaluation of damaged Hair Using shampoo Agents blended with organic ammonium salt

Evaluation of repeated treatments Using damaged Hair

The damaged hair was treated repeatedly 10 times in the same manner as in 3-1 above, and the air-dried hair was evaluated for cohesiveness, smoothness of the hair surface, and waving of the hair.

Watch 15

According to table 15, the hair-damaged hairs of examples B55 and B56 treated with the shampoo solutions to which compound B11 and compound B23 were added were good in aggregation and smoothness of the hair surface, and no wavy hair was observed. On the other hand, the wavy shape of hair was observed in comparative example B19 treated with a shampoo agent to which compound B27 (ion-exchanged water) was added, and the smoothness of the hair surface was poor in comparative examples B18 and 20 using compound B26 (glycerin) and compound B28 (sodium lactate).

From the results, it is suggested that the hair treatment composition using the hair treatment agent of the present invention can impart cohesiveness to hair, smoothness of hair, and suppression of waving of hair even in damaged hair, and can obtain a good feel to the hair.

3-3 sensory evaluation of healthy Hair Using shampoo preparation comprising organic ammonium salt (evaluation Using various anionic surfactants)

Production of Hair treatment composition (shampoo)

0.5 mass% of cationized hydroxyethylcellulose (made by Toho chemical industry Co., Ltd., Catinal HC-200) and purified water were uniformly mixed at 70 to 80 ℃, then each anionic surfactant shown in Table 16 was added so that the content was 11.25 mass% (effective component), coconut oil fatty acid amidopropyl betaine (made by Sanji oil & fat Co., Ltd., AMPHOREX CB-1) was added so that the content was 3.75 mass% (effective component), then each compound B11 or B27 was added so that the content was 3.0 mass% (converted to anhydride content with respect to compound B11), and the mixture was stirred at 70 to 80 ℃ for 20 minutes to uniformly mix. Subsequently, the mixture was cooled to 30 ℃ or lower, and purified water corresponding to the evaporation part was added so that the total amount of the hair treatment composition became 100 mass%, and the mixture was uniformly mixed to produce a hair treatment composition. For the pH of the hair treatment composition, citric acid or sodium hydroxide is added to make pH 6.0.

As the anionic surfactant, sodium lauroyl methyl- β -alanine was Enagicol L-30AN (manufactured by lion corporation, ライオン Co., Ltd.), triethanolamine cocoyl glutamate was Amisoft CT-12S (manufactured by Wako pure chemical industries, Ltd.), and sodium tetradecene sulfonate was Lipolan LJ-441 (manufactured by lion corporation, ライオン Co., Ltd.).

Evaluation of repeated treatments with healthy wool

About 5g of healthy hair was immersed in 350ml of a 7-fold diluted aqueous solution of each of the hair treatment compositions (shampoo agents) at 35 to 40 ℃ to wash the hair. Rinsing with 500ml of warm water at 35-40 ℃ for 5 times, drying at 80 ℃ and then air-drying at 25 ℃. The series of treatments of shampooing, rinsing and drying was repeated 5 times to evaluate the luster of the air-dried hair, the softness of the hair and the cohesion of the hair. The photograph of the appearance of the hair after air drying is shown in fig. 2.

TABLE 16

According to table 16, the healthy hairs of examples B57 to B59 treated with the shampoo agent containing the compound B11 were good in hair luster, hair softness, and hair aggregation. On the other hand, the hair of comparative examples B21 to B23 treated with the shampoo agent containing compound B27 (ion-exchanged water) was slightly poor in luster, softness, and cohesion.

Further, as compared with the results in table 12, by blending the shampoo compositions containing the compounds of examples and various anionic active agents, any of the items of gloss, softness, and cohesiveness was excellent (excellent) in examples B57 and B58, and therefore, the product of the present invention can exhibit a higher treatment effect by interacting with the shampoo compositions containing various anionic active agents shown in table 16.

3-4 sensory evaluation of healthy Hair Using Conditioning conditioner (conditioner) containing organic ammonium salt

Production of Hair treatment composition (Conditioning conditioner)

Mixing stearyl alcohol (Kalcol 8688, manufactured by Kajow corporation) 4.5 mass%, behenyl alcohol (Kalcol 220-80, manufactured by Kajow corporation) 2.0 mass%, and phenoxyethanol (Hisolve EPH, manufactured by Toho chemical industries, Ltd.) 0.5 mass%, and heating to 75 deg.C to obtain solution A. Behenyltrimethylammonium chloride (Catinal DC-80, manufactured by tokho chemical industry co., ltd.) was added so as to be 3.0 mass%, dipropylene glycol was added so as to be 5.0 mass%, compounds B11, B23, B26, B27, and B28 were added so as to be 3.0 mass% (in terms of the content of anhydride in compounds B11 and B23), respectively, and a solution obtained by adding purified water and dissolving the mixture at 80 ℃ was defined as solution B. Gradually adding the solution B into the solution A, and stirring the mixture for 20 minutes at the temperature of 75 ℃. Subsequently, the mixture was cooled to 40 ℃ or lower, and purified water corresponding to the evaporated part was added to make the whole hair treatment composition 100 mass%, and the mixture was mixed uniformly to produce a hair treatment composition.

Conditioning conditioner dip evaluation using healthy hair

Approximately 5g of healthy hair was immersed in 150g of a 7-fold diluted aqueous solution of each of the above hair treatment compositions (conditioning conditioners) for 30 minutes at 40 ℃. The hair was rinsed 2 times with 500ml of 35-40 ℃ warm water, dried at 80 ℃ and evaluated for combing, cohesion and non-stickiness after air-drying at 25 ℃. The photograph of the appearance of the hair after air drying is shown in fig. 3.

TABLE 17

According to table 17 and fig. 3, the healthy hairs of examples B60 and B61 treated with the conditioning conditioner containing compound B11 and compound B23 were good in combing property and hair cohesion, and no stickiness was felt in the hair. On the other hand, the hair of comparative example B25 treated with the conditioning conditioner containing Compound B27 (ion-exchanged water) was slightly inferior in combing property and poor in hair cohesion. In comparative example B24 in which compound B26 (glycerin) was used, hair was slightly poor in hair-setting property and stickiness. In comparative example B26 in which compound B28 (sodium lactate) was used, the hair was slightly less cohesive, and the hair was sticky.

From the results, it was confirmed that a compound having a salt structure of cation and anion as in the examples shows a good effect as a conditioning conditioner. Further, the compounds of examples were more excellent in sensory evaluation than compound B28 (sodium lactate), and therefore, it is suggested that the effect of the organic ammonium salt having a hydrogen-bonding functional group in the cation and anion and being liquid at 25 ℃ is higher.

4. Evaluation of adhesion and stabilization of protein (keratin) to hair and skin

4-1. Keratin attachment

To 2g of a 50 wt% aqueous solution of compounds B11, B23, B26 and B27, 1g of powdery keratin (manufactured by Tokyo chemical Co., Ltd.) (test pre-keratin) was added, and the mixture was stirred at 25 ℃ for 24 hours. After stirring, filtration was carried out, and the obtained powdery keratin was dried to obtain treated keratin (keratin after the test).

The attachment rate of the compound to keratin was calculated using the following formula.

Compound attachment ratio (%) - (test weight of keratin (g) -test weight of pro-keratin (g))/test weight of pro-keratin (g) ] × 100

From the results in table 18, it was found that the ion-exchanged water of compound B27 in the comparative example did not adhere, the glycerin of compound B26 was 11.0%, and the adhesion rate of the compound in the example was 13.2 to 17.0%, indicating that the hair treatment agent of the present invention has an excellent cationic structure and excellent adhesion of hydrogen-bonding functional groups to proteins (keratin) of hair, for example, skin such as keratin and nails.

4-2 evaluation of Effect of Hair treatment agent on Keratin stabilization

0.3g of the treated keratin obtained in 4-1 was allowed to stand in a thermostat at 130 ℃ for 7 days. After 7 days, the effect of the hair treatment agent on stabilizing the keratin structure was evaluated by measuring the IR spectrum of the obtained keratin and measuring the absorption of the α -helical secondary structure from the amide.

The keratin powder before heating was measured by IR, and found to be 1654cm in the secondary structure of a-helix derived from amide^-1Absorption was observed. Then, IR measurement after the 130 ℃ heating test was carried out to obtain a peak derived from each amide and an intensity ratio to the base peak (derived from C-N) of 1086cm^-11654cm of a peak derived from the alpha-helical secondary structure of the amide^-1). For the intensity ratio (X), the absorption intensity of the base peak and the intensity of the peak from the amide were read as "base peak intensity: peak intensity from amide 1: x' was evaluated.

From the results in table 18, it was confirmed that the peaks derived from the α -helical secondary structure of amide of the ion-exchanged water of compound B27 of the comparative example disappeared and the α -helical secondary structure of keratin was not retained. On the other hand, it was confirmed that the glycerol of compound B11, B23 and compound B26 of the examples retained the α -helical secondary structure of keratin because the peak derived from the α -helical secondary structure of amide was confirmed, and the glycerol of compound B26 of the comparative example had an intensity ratio of the peak derived from the α -helical secondary structure of amide to the base peak of 0.3. On the other hand, the intensity ratio of the peak derived from the α -helical secondary structure of the amide was as high as 0.6 to 0.9 for the compound of example, and it is suggested that the effect of stabilizing the α -helical secondary structure of keratin is high. As described above, the hair treatment agent of the present invention has a keratin stabilizing effect, and therefore can moisturize and keep the hair healthy, can keep the hair quality, can inhibit hair damage caused by heat such as a hair dryer, and can moisturize and keep the skin protein such as keratin and nails, and can keep the hair healthy.

Watch 18

5. Evaluation of solubility of active ingredient

The solubility of the active ingredients in the compositions described in table 19 was evaluated. As the active ingredient, gallic acid and glutamic acid with antioxidant and moisturizing effects are used. The solubilities of comparative example B29 (aqueous glycerol solution) and B30 (ion-exchanged water) in which glutamic acid was dissolved were < 0.08g, whereas the solubility of example B64 was as high as 0.24 g. In addition, gallic acid also tends to be similar, and compound B11 can dissolve more active ingredients. Therefore, the hair treatment agent of the present invention can be used as a base for a hair treatment composition, a solvent, or a carrier in hair.

Watch 19

6. Evaluation of affinity for Hair (contact Angle)

The hair was immersed in a 50 wt% aqueous solution of compounds B11, B12, B29 and B24 described in table 20 for 5 minutes, rinsed 1 time with warm water, and the hair dried with a towel and the untreated product were dried with a hair dryer (about 100 ℃) (condition a), and then 10 μ L of water was dropped onto each hair to measure the contact angle of the droplet. Contact angle measurement was performed by using a droplet shape analyzer DSA30 (manufactured by KRUSS corporation), by fixing 20 treated hairs on a slide glass with a transparent tape (Sellotape, registered trademark) to a uniform level, dropping 10 μ L of water from above, measuring the contact angle of the droplets, drying the treated hairs and the untreated hair using a 50 wt% aqueous solution of compounds B11, B12, B29, B24, and B26 using a hair iron (160 ℃) at a temperature higher than that of a hair dryer (condition B), and measuring the contact angle under the same conditions as above.

As a result, examples B66 to B68 of condition a had lower contact angles and excellent affinity for hair in all cases of the compounds, as compared with comparative examples B33 and B34. In particular, compound B11 of example B66 had a high affinity to penetrate into the hair, and exhibited effects on hair moisturization, hair health, and hair quality maintenance.

As a result, examples B69 to B71 of condition B had lower contact angles and excellent affinity for hair in all the cases of the compounds, as compared with comparative examples B35 to B37. In particular, the compounds B11 and B12 of examples B69 and B70 had a high affinity to penetrate into the hair, whereas the glycerol of comparative example B36 volatilized, and gave the same results as the untreated ones. From the results, it was confirmed that the compound remained under the condition B of heating condition due to the nonvolatile organic ammonium salt, and the effects of moisturizing hair, health of hair, and hair quality maintenance were exhibited.

TABLE 20A

TABLE 20B

This shows that the organic ammonium salt of the present invention has excellent affinity with hair, exerts its effect without volatilization even after heating in a dryer or the like, and causes little damage to the stratum corneum.

7. Evaluation of protein stability (DSC)

Each hair sample was prepared by immersing compounds B11, B12, B29 and B26 in a 50 wt% aqueous solution for 5 minutes, rinsing with warm water 1 time, and drying the towel-dried hair and the untreated article with a hair dryer (about 100 ℃ C.) (Condition A) or drying the hair and the untreated article treated in the same manner as above with a hair iron (160 ℃ C.) having a higher temperature than that of the hair dryer (Condition B). Each hair sample was cut into a powder, 5mg of the powder was precisely weighed and placed in an SUS container, 10. mu.L of distilled water was added thereto, the container was sealed, and the container was allowed to stand for 2 days to sufficiently contain water. The sample was subjected to DSC measurement under conditions of a nitrogen flow of 60ml/min, a temperature range of 30 to 210 ℃ and a temperature rise rate of 10 ℃/min, and the endothermic peak area was calculated. The endothermic peak area (. DELTA.H) represents the difference obtained by subtracting the endothermic peak area after the treatment from the endothermic peak area of the untreated product. For the evaluation, the smaller the difference from the value before the treatment under conditions a and B (endothermic peak area 34.5 (J/g-hair)), the smaller the change in the crosslinking strength of the keratin protein of the hair main component in the state of the microfibers inside the hair, indicating that the hair is less damaged.

It was confirmed that the peak areas of examples B72 to B77 were closer to the values before treatment than the endothermic peak areas of comparative examples B38 and B39, and the results showed that the examples had less damage to the hair. The peak areas of examples B72 and 75 were not calculated because the peak derived from the compound and the endothermic peak overlapped. It was confirmed that the organic ammonium salt of the present invention having a salt structure is excellent in its effect of suppressing damage, in terms of the value of the endothermic peak area (. DELTA.H), among which a hydroxyl group is more preferable in the anion, as compared with glycerin of comparative example B38. Thus, the hair treatment agent of the present invention suggests that retention of secondary structure and bond cleavage can be suppressed by the interaction between the organic ammonium salt having a hydrogen-bonding functional group and the protein in the hair, and denaturation of the protein can be suppressed, so that the texture after hair treatment can be maintained, and further, the effect of stabilizing the protein of the scalp can be achieved.

TABLE 21

[3] Evaluation of skin-protecting agent

(Compound (I))

Compounds C1-C101

Compounds C1 to C101 shown in tables 22 to 41 were synthesized by the following methods.

Compounds C1-C5: synthesized by the method described in Japanese patent laid-open No. 2014-131975.

Compounds C6-C26: synthesized by the method described in Japanese patent application laid-open No. 2014-131974.

Compounds C27-C39: synthesized by the method described in Japanese patent laid-open No. 2012-031137.

Compounds C40-C61, C65-C95: synthesized by the method described in Japanese patent application publication No. 2018-136893.

Compound C62: a reagent (tetrabutylammonium bromide) manufactured by Wako pure chemical industries, Ltd. was used.

Compound C63: a reagent (1-butyl-3-methylimidazolium tetrafluoroborate) produced by Tokyo Kasei K.K. was used.

Compound C64: a reagent (glycerol) manufactured by Wako pure chemical industries, Ltd.

Compound C96: a reagent (sodium lactate) manufactured by Wako pure chemical industries, Ltd.

Compound C97: a reagent (potassium lactate) manufactured by Wako pure chemical industries, Ltd.

Compound C98: a reagent (ascorbic acid) manufactured by Tokyo Kabushiki Kaisha was used.

Compound C99: a reagent (ascorbic acid glucoside) manufactured by Tokyo Kaisha was used.

Compound C100: a reagent (sodium ascorbyl phosphate) manufactured by Tokyo chemical Co., Ltd was used.

Compound C101: sodium ascorbyl phosphate was neutralized with hydrochloric acid, and after desalting, the resulting ascorbyl phosphate was neutralized with 2-amino-2-hydroxymethyl-1, 3-propanediol to give a compound.

The organic ammonium salts of the present invention in the examples in tables 22 to 42 were produced according to production method B described in [2] evaluation 1-3 of hair treatment agent, except for C25 to 39 and C57 to 59.

(evaluation method)

(1) Water retention test 1

As to the compounds C1 to C61, 80 wt% aqueous solutions of the compounds C62 to C64 of comparative examples were prepared, and it was confirmed that the water content was 20.0 wt% (water content before test: A) by Karl Fischer water content meter (CA-200, manufactured by Mitsubishi chemical analysis, Inc. (Mitsubishi ケミカルアナリテック)). 1.0g of these samples were put into a screw tube and left to stand without a lid in a constant temperature and humidity apparatus (KCL-2000W, manufactured by Tokyo chemical and physical instruments Co., Ltd.) set at 40 ℃ and 25% RH for 24 hours. The water content after 24 hours (water content after test: B) was measured again, and the water retentivity was evaluated by calculating the water content decrease rate using the following equation.

Moisture percentage before test: a (%).

Moisture percentage after test: b (%).

Moisture reduction rate (%) [ (a (%) -B (%)/a (%) ] × 100

As a result, the water content of the compounds C1 to C61 was reduced and the water retentivity was improved in the 80 wt% aqueous solution as compared with the compounds C62 to C64 of the comparative examples. In addition, the liquid property is maintained. The compound in the hydrate state was subjected to a reduced pressure treatment to prepare an anhydride, and the appearance of the anhydride state at 25 ℃ was confirmed and shown in the table.

It is suggested that the compounds C1 to C61 which are organic salts having a hydrogen-bonding functional group (hydroxyl group) in the cation and/or anion have a hydrogen-bonding functional group, but the water content reduction rate is smaller and the water retentivity of the organic ammonium salt is higher than that of the compound C64 which is not a salt structure.

The compounds C12 to C14, C18, C19, C35, C37, and C38 having only a hydrogen-bonding functional group in the cation and the compound 39 having only a hydrogen-bonding functional group in the anion have a smaller moisture reduction ratio than the compounds C62 and C63 of the comparative examples having no hydrogen-bonding functional group, and the organic ammonium salt having a hydrogen-bonding functional group in either the cation or the anion has an excellent water retentivity.

When compared with the compound C39 having a hydrogen-bonding functional group only in the anion, the compounds C1, C2, C5, C8, C15, C20, C23, C24, C25, C26, C29, C43, and C46 having a hydrogen-bonding functional group introduced into the cation and the anion have a smaller moisture reduction rate than the compounds C12 to C14 having a hydrogen-bonding functional group only in the cation, and when compared with the same cation, the compounds C6 to C11 having a hydrogen-bonding functional group introduced into the cation and the anion have a smaller moisture reduction rate than the compounds C12 to C14 having a hydrogen-bonding functional group only in the cation, and thus, it is confirmed that the water retention effect is excellent.

When a combination of substituents of a cation is compared with an organic salt of the same anion (lactic acid anion), a compound having a hydroxyalkyl group and/or a hydrogen atom directly bonded to nitrogen in the cation and optionally having an alkyl group, C1, C2, C5, C8, C15, C20, C23, C24, C25, C26, C29, C43, or C46 has a smaller moisture reduction rate than a compound C39 composed only of an alkyl group, and therefore, a compound having a hydroxyalkyl group in the cation and a hydrogen atom directly bonded to nitrogen has an excellent water retentivity.

Then, it was confirmed that when the hydrogen-bonding functional groups of the cations were compared, the water-retention effect was excellent when the cations were composed of only hydroxyalkyl groups and/or hydrogen atoms directly bonded to nitrogen, and when the cations were composed of only hydroxyalkyl groups and/or hydrogen atoms directly bonded to nitrogen, the water-retention rate was small in compounds C1, C2, C5, C8, C15, C20, C23, C24, C25, C26, C43, and C46, as compared with the compound C29 in which the cations were composed of hydroxyalkyl groups and alkyl groups.

Further, compounds C1, C2, C5, C8, C15, C20, C23, C24, C43 and C46 having a small water content decrease ratio and containing 1 or more hydrogen atoms directly bonded to nitrogen have excellent water retention properties as compared with compounds C25, C26 and C39 having no hydrogen atoms directly bonded to nitrogen, and compounds C1, C2, C5, C8, C15, C20, C23, C43 and C46 having a cation structure particularly excellent in water retention properties as compared with compound C24 composed of only hydrogen atoms directly bonded to nitrogen exhibit particularly excellent water retention properties.

For the anionic species, a comparison of the anions was made with organic salts of the same cations. As a result of comparing compounds C6 to C11 containing a hydrogen bonding functional group in the anion with compounds C12 to C14, C15 to C17, C18, C19, compounds C27 to C34 and compound C35 containing no hydrogen bonding functional group, it was confirmed that the compounds C6 to C11, C15 to C17, C18 and C27 to C34 containing an anion having a hydrogen bonding functional group had a small moisture reduction ratio. That is, on the other hand, the compound containing an anion of a hydroxyl group, a carboxyl group, a carboxylate group, a sulfonyl group, a phosphate group, or a phosphinate group having a hydrogen-bonding functional group is superior in water retention performance to a halogen-based anion not having a hydrogen-bonding functional group. When compared with a halogen anion, the water retentivity was excellent in the order of the compounds C12 (boron anion), C13 (bromide ion) and C14 (chloride ion).

(2) Water retention test 2

The water retentivity of the hydrate in each compound was evaluated. Since hydrates were used for compounds C1 to C38, C40 to C49, and C56 to C59, and since compounds C39 and C62 to C64 were anhydrous, aqueous solutions prepared by adding water to a concentration of 1 hydrate to 3 hydrate were used. The water content of the sample was confirmed by a Karl Fischer moisture meter (water content before test: A). 1.0g of each sample was put into a screw tube and left to stand in a thermostat set at 40 ℃ and 25% RH for 24 hours without a cover. The water content after 24 hours (water content after test: B) was measured again, and the water retentivity was evaluated by calculating the water content decrease rate in the same manner as described above. Further, the aqueous solutions of the hydrates of the compounds C1 to C38, C40 to C49, and C56 to 59 and the compound C39 at concentrations corresponding to the number of the hydrates were compared and evaluated.

(1 hydrate in examples C62-C99, C103-C116: Compounds C1-C38, C40-C49, C56-C59; and example C100: Compound C39; comparative example C4: Compound C62; comparative example C7: Compound C63; and comparative example C10: Compound C64.)

(2 hydrates of examples C62 to C99, C103 to C116: Compounds C1 to C38, C40 to C49, C56 to C59; and example C101: Compound C39; comparative example C5: Compound C62; comparative example C8: Compound C63; and comparative example C11: Compound C64.)

(3 hydrates of examples C62 to C99, C103 to C116: Compounds C1 to C38, C40 to C49, C56 to C59; and example C102: Compound C39; comparative example C6: Compound C62; comparative example C9: Compound C63; and comparative example C12: Compound C64.)

From the results in tables 25 to 27, the compounds C1 to C49 and C56 to C59 of the examples had a smaller water content decrease rate and more excellent water retentivity than the compounds C62 to C64 of the comparative examples.

The correlation between the molecular structures of the cations and anions and the water retentivity tends to be similar to that in the water retentivity test 1.

The water content decrease rates of the hydrates of the compounds C1 to C13, C15 to C18, C20 to C34, C36, C40 to C49, and C56 to C59 in water retention test 2 of examples were less than the water content decrease rate of the 80 wt% aqueous solution in water retention test 1. The water content of the 80 wt% aqueous solution in the water retention test 1 from before to after the test was larger than that of the hydrate (for example, the 80 wt% water content of the compound C8: 19.2% and the hydrate water content of the compound C8: 16.6%), free water volatilized, while the water content of the hydrate in the water retention test 2 was reduced by volatilization of the water. That is, it is suggested that the hydrate compound has low volatility of the water of hydration, a smaller water reduction rate, and good water retentivity in a range of the water content of the hydrate or less. However, the water reduction rate of the hydrates of the chloride anion compounds C14, C19, C35, C37, and C38 was the same or larger than that of the 80 wt% aqueous solution, and the above tendency was not exhibited.

Further, the tendency of the moisture reduction rate due to the presence or absence of the formation of the hydrate was evaluated. When 1, 2 and 3 hydrates were compared with the same anion, the water content reduction rate was smaller in the hydrate-forming compounds C1, C2, C5, C8, C15, C20, C23, C24, C25, C26, C29, C43 and C46, compared with the compound C39 which is an anhydrate not forming a hydrate, and it was confirmed that the hydrate-forming compound had excellent water retentivity.

(3) Water retention test 3

In the water retention test 3, 80 wt% aqueous solutions of the compounds C8, C11, C62, C63 and C64 were prepared, and after confirming the water content of 20.0 wt% by karl fischer moisture meter, 1g of these samples were put into a screw tube and left to stand in a thermostat set at 40 ℃ and 25% RH without a cover. 24. After 96, 120, 144, 168, 192 hours, the moisture content was measured again by a Karl Fischer moisture meter. On the other hand, the amount of water reduction was calculated by measuring the weight for each time (0 to 24 hours, 24 to 96 hours, 96 to 120 hours, 120 to 144 hours, 144 to 168 hours, and 168 to 192 hours). Further, the water retentivity was evaluated by calculating the amount of water reduction per hour (mg/h) from each amount of water reduction (mg).

From these results, the water content of the compounds C62 and C63 in the comparative examples was less than 1% after 96 hours and the water content of the compound C64 was less than 192 hours, whereas the water content of the compounds C8 and C11 in the examples was 15% or more after 192 hours, and the long-term water retention effect of the compounds of the present application having an organic salt having a hydrogen-bonding functional group was confirmed.

The water contents of the hydrates (compound C8: 16.6%, compound C11: 16.1%) and the water contents of the compounds C8 and C11 after 0 to 144 hours (compound C8: 16.5%, compound C11: 16.2%) were substantially equal to or more than the water contents of the hydrates, and the water contents of the hydrates were smaller and the water of hydrates volatilized between 144 to 192 hours. The amount of water reduction per hour from 0 to 144 hours for volatilization of free water of the compounds C8 and C11 was 0.3mg/h, whereas the amount of water reduction per hour from 144 to 192 hours for volatilization of hydrated water was reduced to 0.2 mg/h. That is, the volatility of the hydrated water is small, suggesting that the hydrated compound has an excellent water retention effect for a long period of time.

(4) Water blocking test (Barrier property)

The resulting mixture was coated on a quantitative 5C filter paper (Toyo Boseki paper) cut into 3 cm. times.3 cm in size with a thickness of 0.01mL/cm²80 wt% aqueous solution of the compounds C8, C11, C20, C29, C43, C46, C47, C49-C55, and C62-C83. Then, 20.0g of ion-exchanged water was put into a 40mL vial (manufactured by Aswanese corporation, Japan, アズワン), an inner cap (rubber stopper) of the vial (pierce virtual bottle) was removed, and the filter paper coated with each sample was put on the vial and then closed with the outer cap. The resulting mixture was placed in a constant temperature and humidity apparatus set at 40 ℃ and 25% RH, and allowed to stand for 24 hours, and the weight of ion-exchanged water in the vial was measured.

The amount of water evaporated from the filter paper coated with ion-exchanged water alone W (g) and the amount of water evaporated from the filter paper coated with the sample S (g) were set, and the weight of ion-exchanged water in the vial before storage was Wm₁The weight of ion-exchanged water in the vial after 24 hours was set to Wm when the vial was set to 20.0g₂The water evaporation inhibition rate (%) was calculated from the following formula, and the water clogging property was evaluated. The higher the value of the moisture blocking property, the more excellent the moisture blocking property is. In addition, Wm in the following formula₁、Wm₂、Sm₁、Sm₂Each represents the following numerical value.

Wm₁: weight of ion-exchanged water in vial before storage (using filter paper coated with ion-exchanged water only)

Wm₂: weight of ion-exchanged water in the vial after 24 hours (using filter paper coated with ion-exchanged water only)

Sm₁: weight of ion-exchanged water in vial before storage (using filter paper coated with sample)

Sm₂: weight of ion-exchanged water in the vial after 24 hours (using filter paper coated with sample)

Water evaporation amount W (g) ═ Wm₁-Wm₂

Water evaporation amount S (g) Sm₁-Sm₂

Water evaporation inhibition rate (%) [ (w (g) -s (g))/w (g) ] × 100

The results of the moisture blocking test are shown in table 8.

Watch 29

The water evaporation inhibition ratios of comparative examples C16 to C18 were 16.2 to 29.5%, while the water evaporation inhibition ratios of the compounds of the examples were 30.3 to 42.3%, confirming that the compounds of the examples had excellent water clogging properties.

In addition, while precipitation of crystals was observed after the test on the filter paper coated with the compound C62 of the solid comparative example C16 at room temperature, precipitation of crystals and the like was not observed on the filter paper of the compound of the liquid example, and the coating property, permeability, and appearance after drying of the liquid were more excellent than those of the solid. In addition, it is suggested that the effect is maintained for a long period of time when the active ingredient is dissolved.

Further, when compounds C8, C11, C20, C29, C43, C46, C47, C49 to C55, and C65 to C83 in examples were compared with compounds C62, C63, and C64 in comparative examples, the water evaporation inhibition ratio of compound C64 in comparative example was lower, and the water evaporation inhibition effect was confirmed to be a compound having a salt structure which is preferably nonvolatile. Further, it was confirmed that when compounds C8, C11, C20, C29, C43, C46, C47, C49 to C55, and C65 to C83 of examples having a salt structure were compared with compounds C62 and C63 of comparative examples, the water evaporation suppression efficiency of the compounds of examples was higher, and the water evaporation suppression effect was further improved by having a hydrogen-bonding functional group in the salt structure.

(5) Sensory evaluation

Each of the compounds described in examples C152 to C191 and comparative examples C19 to C21 in tables 30 and 31 was diluted to a predetermined concentration and put into a spray bottle, and a certain amount of the diluted solution was sprayed onto the skin to evaluate the moisturizing feel, non-stickiness, and skin compatibility at the time of application. For the groups, 5 were randomly selected regardless of age, and the average value was calculated as the evaluation value.

The moisturizing feeling after application was evaluated by applying an aqueous solution of each compound on a scale of 5 on the basis of the feel of the skin at the time of application, and the case where the moisturizing feeling was felt largely was evaluated as 5, the case where the moisturizing feeling was felt was evaluated as 3, and the case where the moisturizing feeling was not felt was evaluated as 1.

The stickiness after application was evaluated by applying an aqueous solution of each compound on a scale of 5 based on the feel of the skin at the time of application, and the case of no stickiness was evaluated as 5, the case of slight stickiness was evaluated as 3, and the case of stickiness was evaluated as 1.

For the skin compatibility after application, the aqueous solutions of the respective compounds were applied and evaluated in 5 grades based on the feel of the skin at the time of application, and the case of good compatibility was evaluated as 5, the case of compatibility was evaluated as 3, and the case of poor compatibility was evaluated as 1.

TABLE 30A

TABLE 30B

Watch 31

From table 30, it was confirmed that when examples C152 to C185 and comparative examples C19 to C21 using an organic ammonium salt were compared at the same concentration, the feeling of use was excellent in any of moisturizing feeling, non-stickiness, and skin compatibility.

From table 31, it was confirmed that the organic ammonium salt using the fatty acid anion having 18 carbon atoms as an anion was also excellent in any of the moist feeling, non-stickiness, and skin-compatible feeling.

Thus, the skin care agent of the present invention is suggested to be excellent in feeling of use when applied to the skin, and is preferable as a skin care agent. In particular, as in examples 152 to 191, the starting materials (acid, base) for the cation and anion of the organic ammonium salt are described in Japanese Standard drug substance standards, and it can be said that the safety is high.

(6) Surface resistance measurement of organic ammonium salt

0.7g of each of the compounds C20 and C64 (in terms of the content of anhydride) was applied to an artificial leather made of polyurethane, and the surface resistance value was measured using a high resistance meter (Stack TR-2, manufactured by Tokyo electronic Co., Ltd.). Greater than 4X 10 in a state of no coating¹¹Omega, on the other hand, all liquids were measured, and Compound C20 was less than 1X 10⁸Omega, Compound C64 is 5X 10⁸Therefore, compound C20 has advantages over compound C64 in that the coating surface has good conductivity, suppresses static electricity, has an antistatic effect, and exhibits the structural characteristics of the skin care agent of the present invention.

Further, 0.7g (in terms of anhydrous content) of compound C96 (sodium lactate) was applied to the polyurethane artificial leather, and the resultant was dried to evaporate water, so that the applied surface became solid, and the surface resistance value measured in the same manner as described above was 2 × 10⁸Omega, therefore, Compound C20 (less than 1X 10) was confirmed⁸Ω) and the effect of being liquid at 25 ℃ (uniform application to a coated material).

This suggests that the skin care agent of the present invention is excellent in antistatic properties and contributes to reduction of adhesion of dust to the skin and entanglement of clothes due to static electricity.

(7) Evaluation of solubility of active ingredient

The solubility of the active ingredients in aqueous solutions of compounds C20 and C64 shown in table 32 was evaluated. As the active ingredient, gallic acid and glutamic acid with insoluble antioxidant effect and moisturizing effect are used. The solubility of glutamic acid in comparative example C22 (glycerol 23 wt% aqueous solution), C23 (ion exchanged water) was less than 1 wt%, and the solubility in example C192 (compound C20 23 wt% aqueous solution) was up to 3 wt%. In addition, gallic acid also has the same tendency, and can dissolve more effective components. Thus, the skin care agent of the present invention can be used as a base, a solvent, a carrier, and the like of a skin care composition.

Watch 32

(8) Skin irritation test

For Compound C20, a skin irritation test was carried out using a three-dimensional human culture epidermal MODEL "LabCyte EPI-MODEL" (manufactured by Nippon Tech Co., Ltd. (J-TEC)). For the test, an aqueous solution of compound 20 (concentration: 0.1, 1, 10, 25, 50 wt/v% aqueous solution, addition amount: 500. mu.L) was added to human epidermal tissue, and at the exposure time: 24 hours, test temperature: 37 ℃, test conditions: CO 2₂Incubator (CO)₂5-10%) of the active component in the aqueous solution. After standing, the compound 20 aqueous solution was removed, washed 3 times with 500. mu.L of phosphate buffer, and then separately injected into 500. mu.L of MTT (3- (4, 5-dimethylthiazol-2-yl) -2, 5-diphenyltetrazolium bromide) medium, and CO was added thereto₂The incubator was allowed to stand at room temperature for 3 hours, the bluish purple human epidermal tissue derived from the product of the reaction of reductase in the stained viable cells with MTT was taken out, the tissue was placed in a microtube together with 300. mu.L of isopropyl alcohol (IPA), a pigment was extracted at room temperature for 2 hours, the absorbance (570nm) of each of the obtained IPA extracts was measured by a microplate reader, the absorbance of the IPA extract of the human epidermal tissue treated with purified water in the same manner was set to the viable cell ratio of 100% as a negative control, and the viable cell ratio of each substance was determined from the relative value of the absorbance. The case where the living cell rate was more than 50% was evaluated as non-irritant, and the case where the cell rate was 50% or less was evaluated as irritant. The above test was carried out with n ═ 2. The results are shown in Table 33.

Watch 33

From the results of table 33, it was confirmed that compound C20 exhibited a high viable cell rate at any concentration, which was low irritativeness. From the results, it is suggested that the cosmetic including the skin care agent and the hair treatment agent of the present invention has low irritation to the skin.

(9) Patch test

For compound C20, according to the closed patch test: "method of performing skin irritation/sensation test and skin property measurement and evaluation" chapter 1: skin irritation test, section 3: the patch test (p29) was carried out by the following test method for 24-hour blocking patch test. The judgment criteria are shown in tables 34 and 35.

Watch 34

National standard	Scoring	Reaction of
			-	0	No reaction
±	0.5	Mild erythema
			+	1	Marked erythema
++	2	Erythema, edema, papules
			+++	3	Erythema, edema, pimple and vesicles
++++	4	Big bubble

Watch 35

Index of skin irritation	Classification in 1995
		5.0 or less	Security article
Greater than 5.0 and less than 15.0	Permissive article
		Greater than 15.0 and less than 30.0	To-be-modified product
Greater than 30.0	Hazardous article

(test method)

1) In a patch test unit, compound C20(85.4 wt% aqueous solution), 15 μ L of a control substance, and an amount of white petrolatum that can be appropriately evaluated were applied to the filter paper on the chamber.

2) The predetermined patch part of the subject was observed before the patch was attached, and the suitability was confirmed. The patch test unit manufactured by the patch is blocked at the patch part.

3) The patch test unit was removed 24 hours after the patch application, and the patch portion of each sample was marked by the 4-point method after lightly wiping with a nonwoven fabric wetted with purified water. After 60 minutes of removal and after 24 hours.

The implementation mechanism comprises: marble laboratory corporation (Marble 12521; 12508

(test results)

20 subjects were subjected to a 24-hour blocking patch test against human skin, and no erythema response was observed in all subjects. The skin irritation index was 0.0, and classified as "safe" according to the classification of skin irritation index based on perfume and cosmetics. From these results, it is suggested that the cosmetic including the skin care agent and the hair treatment agent of the present invention is highly safe.

(10) Feeling of use of emulsion composition containing organic ammonium salt

Emulsion compositions of examples C199 to C203 and comparative examples C26 to C35 were produced in accordance with the compositions shown in Table 36, and the feel in use was evaluated. Specifically, the oil agent and the surfactant are heated to 80 ℃ to be uniformly dissolved. Subsequently, while maintaining the temperature, a solution in which the organic ammonium salt and the ion-exchanged water were uniformly dissolved was gradually added, stirred at 80 ℃ for 3 minutes, and cooled to 25 ℃. As a result of measuring the electric conductivity of the obtained emulsified composition, the electric conductivity was low, the continuous phase was an oil phase, and the obtained emulsified composition was judged to be a W/O type emulsion.

The evaluation method of the feeling of use was to place a certain amount of the emulsified composition on the skin and evaluate spreadability, hair stickiness, moisturizing feeling, sustained moisturizing feeling, skin compatibility, and skin elasticity when the emulsified composition was applied. For the groups, 5 were randomly selected regardless of age, and the average value was calculated as the evaluation value.

Spreadability during coating was evaluated in 5 grades, and the case where the emulsion composition was well spread was evaluated as 5, the case where the emulsion composition was spread was evaluated as 3, and the case where the spreadability was not good was evaluated as 1. The average value of each group was taken as an evaluation value.

The stickiness after application was evaluated by applying the emulsion composition on a scale of 5 based on the feel of the skin at the time of application, and the case of no stickiness was evaluated as 5, the case of slight stickiness was evaluated as 3, and the case of stickiness was evaluated as 1. The average value of each group was taken as an evaluation value.

The moisturizing feeling after application was evaluated by applying the emulsion composition on a 5-point scale based on the feeling of the skin when applied, and the case where a large moisturizing feeling was felt was evaluated as 5, the case where a moisturizing feeling was felt was evaluated as 3, and the case where a moisturizing feeling was not felt was evaluated as 1. The average value of each group was taken as an evaluation value.

The sustained moisturizing feeling after application was evaluated by applying the emulsion composition and evaluating it on a 5-point scale based on the feel of the skin 2 hours after application, and the case where a large sustained moisturizing feeling was felt was evaluated as 5, the case where a sustained moisturizing feeling was felt was evaluated as 3, and the case where a sustained moisturizing feeling was not felt was evaluated as 1. The average value of each group was taken as an evaluation value.

For skin compatibility, 5 grades were evaluated, and the case of good compatibility was evaluated as 5, the case of compatibility was evaluated as 3, and the case of poor compatibility was evaluated as 1. The average value of each group was taken as an evaluation value.

The skin elasticity was evaluated in 5 grades, and the skin was evaluated as 5 when the skin was felt to have full elasticity, 3 when the skin was felt to have slight elasticity, and 1 when the skin was not felt to have elasticity. The average value of each group was taken as an evaluation value.

Watch 36

From table 36, it was confirmed that the examples using the organic ammonium salt were excellent in all of spreadability, hair tackiness, moisturizing feeling, skin compatibility, and feeling of use of skin elasticity, compared to the comparative examples using glycerin. In particular, the sustained humectant feel, which is excellent in all the examples, suggests the effect of the nonvolatile organic ammonium salt. In particular, examples C200 and C202, which contained liquid paraffin and silodosin in large amounts as oil agents, were confirmed to have significantly improved spreadability, moisturizing feeling, and feeling of use for skin compatibility.

Next, as shown in table 37, gels having a different form from the emulsion composition (W/O) and a feeling of use of the emulsion composition (O/W) were also evaluated. Specifically, as a method for producing the gel (examples C204 and C205), the surfactant and the oil agent were heated to 80 ℃ to be uniformly dissolved. Subsequently, the organic ammonium salt aqueous solution was slowly added while maintaining the temperature, and stirred and mixed at 80 ℃ for 3 minutes. As a method for producing the emulsion composition (O/W) (example C206), specifically, an organic ammonium salt or concentrated glycerin was uniformly dissolved in ion-exchanged water at room temperature. Subsequently, the oil agent was slowly added, followed by stirring for 3 minutes. Further, the conductivity of the obtained emulsion was measured, and as a result, the conductivity equivalent to that of ion-exchanged water was obtained, and it was confirmed that the continuous phase was an aqueous phase, and the obtained emulsion was judged to be an O/W emulsion.

The feel of use of examples C204 to C206 was similar to that of the emulsion composition (W/O) containing an organic ammonium salt, and was more excellent in spreadability, hair tackiness, moisturizing feel, skin compatibility and skin elasticity than the emulsion composition containing glycerin instead of the organic ammonium salt.

Watch 37

(11) Affinity to skin

With respect to 50 wt% aqueous solutions of compounds C20 and C64 and ion-exchanged water, the affinity for skin was evaluated by contact angle measurement. The contact angle was measured by using a droplet shape analyzer DSA30 (manufactured by Kruss corporation), and the droplet volume was 20. mu.L. Samples prepared at each concentration of 20. mu.L were dropped onto the arms of each group, and the contact angle was measured every 1 minute. For the groups, 5 were randomly selected regardless of age, and the average value was calculated as the evaluation value. The results are shown in Table 38.

Watch 38

According to example C207 and comparative examples C36 and C37, it was confirmed that compound C20 has a smaller contact angle than compound C64 and ion-exchanged water, and has excellent affinity with the skin and skin compatibility. In addition, it was confirmed that the contact angle significantly decreased with time and the affinity was good. This suggests that the skin care agent of the present invention has better skin compatibility than glycerin and ion-exchanged water.

(12) Long term retention of skin

The long-term adhesion to the skin was evaluated by contact angle measurement for compounds C20 and C64. The evaluation method was carried out by applying a30 wt% aqueous solution of compounds C20 and C64 and ion-exchanged water to the arms of each group, dropping 20. mu.L of ion-exchanged water immediately after, 5 minutes after, and 10 minutes after the application of the sample to the arms, and measuring the contact angle. The contact angle was measured by using a droplet shape analyzer DSA30 (manufactured by KRUSS corporation). For the groups, 5 were randomly selected regardless of age, and the average value was calculated as the evaluation value. The results are shown in Table 39.

Watch 39

The contact angle of ion-exchanged water was smaller in example C208 (compound C20) than in comparative example, suggesting that the affinity of skin with ion-exchanged water was improved.

For example C208 (compound C20), the contact angle of ion-exchanged water to the skin immediately after application for 10 minutes also did not change, indicating that the affinity to the skin was maintained for a long period of time. Further, the contact angle was confirmed after 30 minutes, and as a result, the value after 10 minutes of holding indicates that the film does not volatilize and has high long-term retention to the skin. For comparative example C38 (compound C64), it was confirmed that the contact angle of ion-exchanged water after coating increased with time, approaching that of comparative example C39 (ion-exchanged water). It is presumed that the volatilization of glycerin causes a decrease in adhesion to the skin.

Thus, the skin care agent containing an organic ammonium salt of the present invention can maintain the effects of the present invention including the moisture retention property and the persistence of the effect of the active ingredient on the skin for a long period of time due to the non-volatility and affinity of the organic ammonium salt to the skin. Further, it is a liquid, and it is presumed that even coating on the surface for a long time improves these effects.

(13) Permeability to the skin

Skin permeability was evaluated using the stratum corneum tape stripping method. The compound C20 of the example and the compounds C64 and C97 of the comparative example shown in table 40 were used. The sample was applied to the arm, and the horny layer left for 1 hour was peeled off with 8 layers of adhesive tape. The deposit on the tape was extracted with ion-exchanged water for 10 minutes, and the amounts of compounds C20, C64 and C97 in each extract obtained by filtering the obtained extract with a 0.2 μm filter were quantified by HPLC.

As a result of the quantitative determination, in the tape release layers of the 1 st to 8 th layers, since the concentration of the compound C20 of the example in the extract liquid was higher than that of the compounds C64 and C97 of the comparative examples, it was confirmed that the compound of the example had higher permeability to the stratum corneum surface. Therefore, the skin care agent of the present invention has high skin permeability and can be used as a base, a solvent, a carrier, and the like of a skin care composition.

Watch 40

(14) Stability of ascorbic acid-based compound

With respect to 33 wt% aqueous solutions of the compounds C46, C49, and C98 to C100 and water, stability evaluation in the state of the aqueous solution was carried out by visual observation. The evaluation method was carried out by preparing a 33 wt% aqueous solution of the compounds C46, C49, and C98-C100, allowing the solution to stand at room temperature or in a thermostatic bath at 50 ℃ for 7 days, and visually observing the coloration before and after the solution. The evaluation criteria are as follows.

Very good: is colorless and transparent.

Good: light yellow.

And (delta): yellow.

X: dark brown to black.

Ascorbic acid is colored by decomposition. As a result of the evaluation, the compounds C46 and C49 of the examples having a salt structure of ascorbic acid showed a significant improvement in coloring as compared with the compound C98 of comparative example C42, and therefore, the effect of stabilizing the ascorbic acid-based compound in an aqueous solution state due to the salt structure of ascorbic acid was confirmed. Further, the stability of C46 and C49 was also higher than that of C100 which is a sodium salt, suggesting that the cation of the present invention is effective. Further, the compounds C46 and C49 of the examples gave good results compared to C100. That is, it is suggested that the introduction of the cation of the present invention exhibits an overall excellent stabilizing effect under the conditions of room temperature and 50 ℃ as compared with the ascorbic acid-based compounds C99 and 100 which are generally used in cosmetics, and is highly useful for cosmetics such as skin care products and hair care products.

Table 41

(15) Evaluation of whitening Effect

The whitening effect was confirmed by tyrosinase activity inhibition test with respect to 50 wt% aqueous solutions of compounds C46, C49, and C101. Tyrosinase (SIGMA-ALDRICH) was dissolved in 67mM phosphate buffer (pH6.8) to a concentration of 0.2mg/mL to prepare an enzyme solution. The substrate solution was prepared by dissolving 3mg of D-DOPA and L-DOPA (Tokyo chemical industry) in 10ml of 67mM phosphate buffer. First, 80. mu.L of a 50 wt% aqueous solution of each of the compounds C46, C49 and C101 was added to 64. mu.L of 67mM phosphate buffer, 16. mu.L of an enzyme solution was added thereto, and the mixture was preincubated at room temperature for 10 minutes. Subsequently, 80. mu.L of the substrate solution was quickly added to the pre-incubated solution, and the absorbance at 475nm immediately after the addition of the substrate was measured (A1). Further, the solution was allowed to stand at room temperature for 1 week, and then the absorbance at 475nm was measured (A2).

In addition, the case where ultrapure water was added in place of the compound of example was used as a control, and the absorbance at 475nm immediately after the addition of the substrate (A3) and the absorbance at 475nm after the standing for 1 week (A4) were measured in the same manner as described above.

The inhibition ratio was calculated by the following formula.

Inhibition rate (%) - (100- (a2-a1)/(a4-A3) × 100

As a result of the evaluation, it was confirmed that the organic ammonium salt of the present invention has a skin whitening effect by inhibiting tyrosinase activity. That is, it is suggested that the effect of the active ingredient can be exhibited by embedding the skeleton of the active ingredient in the organic ammonium salt of the present invention.

Watch 42