阅读说明：本技术 4,8,11-十二碳三烯醛用于赋予组合物干净的芳香印象的用途 (Use of 4,8,11-dodecatrienal for imparting a clean aromatic impression to a composition ) 是由 H·布吕泽 R·派尔泽 F·加尔利希斯 S·魏兰德 于 2020-03-13 设计创作，主要内容包括：本发明涉及4,8,11-十二碳三烯醛用于赋予组合物干净的芳香印象的用途。本发明进一步涉及包含4,8,11-十二碳三烯醛和至少一种芳香化学品的组合物,以及涉及包含4,8,11-十二碳三烯醛和选自芳香化学品、表面活性剂、油组分、抗氧化剂、除臭活性剂和溶剂的至少一种附加组分的组合物,其中所述组合物不包含1,5,9-环十二碳三烯。(The invention relates to the use of 4,8,11-dodecatrienal for imparting a clean aromatic impression to a composition. The invention further relates to a composition comprising 4,8,11-dodecatrienal and at least one aromatic chemical, and to a composition comprising 4,8,11-dodecatrienal and at least one additional component selected from aromatic chemicals, surfactants, oil components, antioxidants, deodorant actives and solvents, wherein the composition does not comprise 1,5, 9-cyclododecatriene.)

Use of 4,8,11-dodecatrienal to impart a clean fragrance to a composition.

2. Use according to claim 1, wherein 4,8,11-dodecatrienal is used, which comprises less than 0.2% by weight of 1,5,9-cyclododecatriene, based on the weight of 4,8, 11-dodecatrienal.

3. Use according to any one of the preceding claims, wherein 4,8, 11-dodecatrienol is used, comprising less than 0.1 wt%, preferably less than 0.05 wt% of 1,5,9-cyclododecatriene, based on the weight of 4,8, 11-dodecatrienol.

4. Use of 4,8, 11-dodecatrienol, which does not comprise 1,5,9-cyclododecatriene, as an aroma chemical.

5. Use according to any one of the preceding claims for a composition selected from perfume compositions, body care compositions, hygiene articles, cleaning compositions, textile detergent compositions, compositions for dispensers, foodstuffs, food supplements, pharmaceutical compositions and crop protection compositions.

6. A composition comprising 4,8,11-dodecatrienal and at least one additional component selected from the group consisting of fragrance chemicals, surfactants, oil components, antioxidants, deodorant actives and solvents, wherein the composition does not comprise 1,5, 9-cyclododecatriene.

7. The composition according to claim 6, wherein the composition is selected from perfume compositions, body care compositions, hygiene articles, cleaning compositions, textile detergent compositions, compositions for dispensers, food products, food supplements, pharmaceutical compositions and crop protection compositions.

Background

Aromachemicals, especially perfumes (fragrances), are of interest, especially in the field of cosmetics and cleaning and laundry compositions. Fragrances of natural origin are mostly expensive, the supply is usually limited, and their content, purity, etc. also vary due to fluctuations in environmental conditions. In order to circumvent these undesirable factors, it is therefore of great interest to produce synthetic substances with sensory properties resembling more expensive natural perfumes or with novel and interesting sensory attributes.

Despite the large number of fragrance chemicals, new components are always needed to be able to meet the numerous properties required for an extremely diverse field of application. These include, firstly, the organoleptic properties, i.e. the compound should have favourable odour (olfactory) or taste (gustatory) properties. Furthermore, fragrance chemicals should also have additional positive side properties (secondary properties), such as efficient manufacturing processes, the possibility of providing better sensory attributes due to synergistic effects with other fragrance chemicals, higher stability, higher scalability and/or better staying power in diversified compositions and under certain application conditions.

There is an increasing demand for fragrance chemicals which impart a clean aroma impression (clean aroma impression) to compositions, in particular a clean odor impression (clean odor impression). These properties are of particular interest for the following compositions: such as body care compositions, hygiene articles, cleaning compositions, textile detergent compositions and compositions for fragrance dispensers (perfume dispensers). Of particular interest are fragrance chemicals which can impart one or more different fragrance impressions to a composition thereby contributing to the rich and interesting sensory attributes (especially olfactory attributes) of the composition. Furthermore, in particular with respect to fragrance chemicals which can provide a clean fragrance impression, the persistence (persistence) and the persistence (persistence) are of particular interest in order to obtain a lasting clean impression in the composition and on surfaces treated with the composition.

Summary of The Invention

It is an object of the present invention to provide fragrance chemicals which impart a clean note (clean note) to a composition. It is another object of the present invention to provide fragrance chemicals that can impart long lasting clean notes to compositions and surfaces (e.g., skin and/or textiles) treated with such compositions. Such fragrance chemicals should be stable in a wide variety of compositions.

It has been surprisingly found that 4,8,11-dodecatrienal imparts a clean fragrance to the composition.

WO 2010/086313A 1 describes in examples 1 to 3 the separation of mixtures comprising 4,8, 11-dodecatrienal. This mixture contained 98.2% by weight of 4,8, 11-dodecatrienol, 0.26% by weight of 1,5,9-cyclododecatriene and 0.06% by weight of 4, 8-cyclododecadienone (4, 8-cyclododecanedienon). In example 4, the odor impression of this mixture is described as "strongly reminiscent of fir needles, wood and aldehyde odors". WO 2010/086313 further claims the use of a mixture comprising from 92 to 99.8% by weight of at least one 4,8,11-dodecatrienal and from 0.0001 to 5% by weight of 1,5,9-cyclododecatriene as perfume.

There is no indication or teaching in WO 2010/086313 that 4,8,11-dodecatrienal can be used to impart a clean fragrance to the composition. There is also no indication or teaching in WO 2010/086313 that 4,8,11-dodecatrienal can be used to advantageously impart a long-lasting clean note to the composition.

One embodiment of the present invention therefore relates to the use of 4,8,11-dodecatrienal to impart a clean fragrance to a composition. A further embodiment relates to the use of 4,8,11-dodecatrienal to impart a flax note (linen note) to the composition. A preferred embodiment relates to the use of 4,8,11-dodecatrienal to impart a clean flax note to the composition.

One embodiment of the present invention therefore relates to the use of 4,8,11-dodecatrienal, which does not comprise 1,5,9-cyclododecatriene, as fragrance chemical, preferably as perfume.

It is a further object of the present invention to provide fragrance chemicals which can impart one or more different fragrance impressions, preferably olfactory impressions, to a composition thereby contributing to the rich and interesting fragrance attributes of the composition.

It has been surprisingly found that 4,8,11-dodecatrienal can be used to impart one or more aromatic impressions to a composition, wherein the aromatic impressions are selected from citrus note (citrus note), marine note (marine note), ozone note (ozonic note), and cyclamen note (cyclamen note).

One embodiment of the present invention thus relates to the use of 4,8,11-dodecatrienal to impart citrus trim to a composition. One embodiment of the present invention therefore relates to the use of 4,8,11-dodecatrienal to impart marine touch to a composition. One embodiment of the present invention therefore relates to the use of 4,8,11-dodecatrienal to impart ozone tone to a composition. One embodiment of the present invention therefore relates to the use of 4,8,11-dodecatrienal for imparting cyclamen to a composition.

It is a further object of the present invention to provide a composition which provides a long-lasting fragrance impression to the composition itself and/or to the surface to which it is applied. Examples of such surfaces are human skin or hair in the case of body care or perfume compositions. Examples of such surfaces are textiles in the case of textile detergent compositions or hard surfaces in the case of cleaning compositions.

It has been surprisingly found that compositions comprising 4,8,11-dodecatrienal can impart a long lasting fragrance impression to the composition as well as to the surface to which the composition is applied, especially when applied in combination with other fragrance chemicals. It has surprisingly been found that 4,8,11-dodecatrienal can impart a long-lasting impression to textiles treated with compositions comprising 4,8, 11-dodecatrienal.

A further embodiment of the present invention therefore relates to a composition comprising 4,8,11-dodecatrienal and at least one additional component selected from the group consisting of aromatic chemicals, surfactants, oil components, antioxidants, deodorant actives and solvents, wherein the composition does not comprise 1,5, 9-cyclododecatriene.

A further embodiment of the present invention relates to a composition comprising 4,8,11-dodecatrienal and at least one additional component selected from the group consisting of an oil component, an antioxidant, a deodorant active, and a solvent.

In a preferred embodiment of the invention, the composition is a fragrance composition (aroma composition), more preferably an odor composition (odor composition), more preferably a perfume composition (fragrance composition).

The composition according to the present invention may be selected from, but is not limited to, perfume compositions, body care compositions (including cosmetic compositions and oral dental hygiene products), hygiene articles, cleaning compositions (including dishwashing compositions), textile detergent compositions, compositions for dispensers, food products, food supplements, pharmaceutical compositions and crop protection compositions.

A further embodiment of the present invention relates to a method of imparting clean notes to perfume compositions, body care compositions, hygiene articles, cleaning compositions, textile detergent compositions, compositions for dispensers, food products, food supplements, pharmaceutical compositions and crop protection compositions comprising including 4,8,11-dodecatrienal in a perfume composition, body care composition, hygiene article, cleaning composition, textile detergent composition, composition for dispensers, food product, food supplement, pharmaceutical composition and crop protection composition.

A further embodiment of the present invention relates to a method of imparting a fragrance impression to perfume compositions, body care compositions, hygiene articles, cleaning compositions, textile detergent compositions, compositions for dispensers, food products, food supplements, pharmaceutical compositions and crop protection compositions, which comprises incorporating 4,8, 11-dodecatriene aldehyde free of 1,5,9-cyclododecatriene into perfume compositions, body care compositions, hygiene articles, cleaning compositions, textile detergent compositions, compositions for dispensers, food products, food supplements, pharmaceutical compositions and crop protection compositions.

Non-limiting examples of body care compositions are cosmetic compositions and oral dental hygiene products. A non-limiting example of a cleaning composition is a dishwashing composition.

The pleasant aroma, low volatility and excellent solubility make 4,8,11-dodecatrienal a suitable component in compositions where a pleasant aroma is desired. By virtue of their physical properties, 4,8,11-dodecatrienal has particularly good, almost universal solvent properties for fragrance chemicals and other conventional ingredients in compositions, such as perfume compositions in particular. Thus, the 4,8,11-dodecatrienal described herein can be advantageously combined with fragrance chemicals, thereby enabling in particular the creation of fragrance compositions, in particular perfume compositions, having novel advantageous sensory attributes.

Embodiments of the present invention relate to:

use of 4,8,11-dodecatrienal to impart a clean fragrance to a composition.

Use of 4,8,11-dodecatrienal to impart a clean flax note to a composition.

Use of 4,8,11-dodecatrienal to impart citrus trim to a composition.

Use of 4,8,11-dodecatrienal to impart marine touch to a composition.

Use of 4,8,11-dodecatrienal to impart ozone tone to a composition.

Use of 4,8,11-dodecatrienal to impart cyclamen.

7. Use according to any one of the preceding claims, wherein 4,8, 11-dodecatrienol is used, comprising less than 0.2 wt% of 1,5,9-cyclododecatriene, based on the weight of 4,8, 11-dodecatrienol.

8. Use according to any one of the preceding claims, wherein 4,8, 11-dodecatrienol is used, comprising less than 0.1 wt%, preferably less than 0.05 wt% of 1,5,9-cyclododecatriene, based on the weight of 4,8, 11-dodecatrienol.

9. Use of 4,8, 11-dodecatrienol, which does not comprise 1,5,9-cyclododecatriene, as an aroma chemical.

10. Use according to any one of the preceding claims, wherein the weight ratio of (4E,8Z) -dodec-4, 8, 11-trienol to (4Z,8E) -dodec-4, 8, 11-trienol is in the range of 1:1-2, preferably 1:1-1.5, more preferably 1: 1.1-1.3.

11. Use according to any one of the preceding claims, wherein the amount of (4E,8Z) -dodec-4, 8, 11-trienol and (4Z,8E) -dodec-4, 8, 11-trienol is equal to or greater than 50 wt%, preferably greater than 60 wt%, more preferably greater than 70 wt%, preferably greater than 80 wt%, preferably greater than 90 wt%, preferably greater than 95 wt%, based on the weight of 4,8, 11-dodec-trienol.

12. Use according to any one of the preceding claims, wherein the amount of (4E,8E) -dodec-4, 8, 11-trienol is less than 10 wt%, preferably less than 5 wt%, preferably less than 2 wt%, based on the weight of 4,8, 11-dodecenal.

13. Use according to any one of the preceding claims, wherein the amount of (4Z,8Z) -dodec-4, 8, 11-trienol is less than 10 wt%, preferably less than 5 wt%, preferably less than 2 wt%, based on the weight of 4,8, 11-dodecenal.

14. Use according to any one of the preceding claims for a composition selected from perfume compositions, body care compositions, hygiene articles, cleaning compositions, textile detergent compositions, compositions for dispensers, foodstuffs, food supplements, pharmaceutical compositions and crop protection compositions.

15. Composition comprising 4,8,11-dodecatrienal and at least one additional aromatic chemical selected from geranyl acetate (3, 7-dimethyl acetate)2, 6-octadien-1-yl ester), alpha-hexyl cinnamic aldehyde, 2-phenoxyethyl isobutyrate (Phenylirat)¹) Dihydromyrcenol (2, 6-dimethyl-7-octen-2-ol), methyl dihydrojasmonate (preferably with a cis isomer content of more than 60% by weight) (Hedione⁹，Hedione HC⁹) 4,6,6,7,8, 8-hexamethyl-1, 3,4,6,7, 8-hexahydrocyclopenta [ g ] ring]Benzopyran (Galaxolid)³) Tetrahydrolinalool (3, 7-dimethyloctan-3-ol), ethyl linalool, benzyl salicylate, 2-methyl-3- (4-tert-butylphenyl) propanal (Lysmeral)²) Cinnamyl alcohol, 4, 7-methylene-3 a,4,5,6,7,7 a-hexahydro-5-indenyl acetate and/or 4, 7-methylene-3 a,4,5,6,7,7 a-hexahydro-6-indenyl acetate (Herbaflorat)¹) Citronellol, citronellyl acetate, tetrahydrogeraniol, vanillin, linalyl acetate, styryl acetate (1-phenylethyl acetate), octahydro-2, 3,8, 8-tetramethyl-2-naphthaleneacetone and/or 2-acetyl-1, 2,3,4,6,7, 8-octahydro-2, 3,8, 8-tetramethylnaphthalene (Iso E Super)³) Hexyl salicylate, 4-tert-butylcyclohexyl acetate (Orycone)¹) 2-tert-butylcyclohexyl acetate (Agrumex HC)¹) Alpha-ionone (4- (2,2, 6-trimethyl-2-cyclohexen-1-yl) -3-buten-2-one), n-alpha-methylionone, alpha-isomethylionone, coumarin, terpinyl acetate, 2-phenylethyl alcohol, 4- (4-hydroxy-4-methylpentyl) -3-cyclohexenecarbaldehyde (Lyral)³) Alpha-amyl cinnamic aldehyde, ethylene glycol brassylate, (E) -and/or (Z) -3-methylcyclopentadec-5-enone (Musconen)⁹) 15-pentadecyl-11-ene lactone and/or 15-pentadecyl-12-ene lactone (globalite)¹) 15-cyclopentadecanolide (Macrolide)¹) 1- (5,6,7, 8-tetrahydro-3, 5,5,6,8, 8-hexamethyl-2-naphthyl) ethanone (Tonalid)¹⁰) 2-isobutyl-4-methyltetrahydro-2H-pyran-4-ol (Florol)⁹) 2-Ethyl-4- (2,2, 3-trimethyl-3-cyclopenten-1-yl) -2-buten-1-ol (Sandolen)¹) Cis-3-hexenyl acetate, trans-2/cis-6-nonadienol, 2, 4-dimethyl-3-cyclohexenecarbaldehyde (Vertoctral)¹) 2,4,4, 7-tetramethyloct-6-en-3-one (Claritone)¹) 2, 6-dimethyl-5-hepten-1-al (Melonal)²) Borneol and 3- (3-isopropylphenyl) butyraldehyde (Florhdral)²) 2-methyl-3- (3, 4-methylenedioxyphenyl) propanal (Helinal)³) 3- (4-ethylphenyl) -2, 2-dimethylpropionaldehyde (Florazon)¹) 7-methyl-2H-1, 5-benzodioxine-3 (4H) -one (calone), 3, 5-trimethylcyclohexyl acetate (preferably having a cis isomer content of 70% by weight or more), 2,5, 5-trimethyl-1, 2,3,4,4a,5,6, 7-octahydronaphthalen-2-ol (Ambrinol S)¹) 3- (4-tert-butylphenyl) -propionaldehyde (Bourgeonal)⁴) 2-Methylpentanoic acid ethyl ester (Manzanate)⁴) Ethoxy methoxycyclododecane (Amberwood)¹) 2, 4-dimethyl-4, 4a,5,9 b-tetrahydroindeno [1,2-d ]][1,3]Dioxines (Magnolan)¹) 2-tert-butylcyclohexyl acetate (Verdox)³) And 3- [5,5, 6-trimethylbicyclo [2.2.1 ]]Hept-2-yl]Cyclohexan-1-ol (Sandela)⁴)。

16. A composition comprising 4,8,11-dodecatrienal and at least one additional fragrance chemical selected from the group consisting of methyl benzoate, benzyl acetate, geranyl acetate, 2-isobutyl-4-methyltetrahydro-2H-pyran-4-ol, linalool, 2-isobutyl-4-methyltetrahydro-2H-pyran-4-ol, and methyl benzoate.

17. A composition comprising 4,8, 11-dodecatrienol and at least one additional aromatic chemical selected from ethyl vanillin, 2, 5-dimethyl-4-hydroxy-2H-furan-3-one (furaneol) or 3-hydroxy-2-methyl-4H-pyran-4-one (maltol).

18. A composition according to any one of the preceding claims 15 to 17 comprising at least one additional component selected from surfactants, oil components, antioxidants, deodorant actives and solvents.

19. A composition comprising 4,8,11-dodecatrienal and at least one additional component selected from the group consisting of an oil component, an antioxidant, a deodorant active, and a solvent.

20. The composition according to any one of the preceding claims 15 to 19, wherein the composition comprises less than 0.2 wt% of 1,5,9-cyclododecatriene, based on the weight of 4,8, 11-dodecatrienol.

21. The composition according to any one of the preceding claims 15 to 20, wherein the composition comprises less than 0.1 wt.%, preferably less than 0.05 wt.%, based on the weight of 4,8,11-dodecatrienal, of 1,5, 9-cyclododecatriene.

22. A composition comprising 4,8,11-dodecatrienal and at least one additional component selected from the group consisting of fragrance chemicals, surfactants, oil components, antioxidants, deodorant actives and solvents, wherein the composition does not comprise 1,5, 9-cyclododecatriene.

23. The composition according to any of the preceding claims 15 to 22, wherein the weight ratio of (4E,8Z) -dodec-4, 8, 11-trienoal to (4Z,8E) -dodec-4, 8, 11-trienoal is in the range of 1:1-2, preferably 1:1-1.5, more preferably 1: 1.1-1.3.

24. The composition according to any of the preceding claims 15 to 23, wherein the amount of (4E,8Z) -dodec-4, 8, 11-trienol and (4Z,8E) -dodec-4, 8, 11-trienol is equal to or more than 50 wt. -%, preferably more than 60 wt. -%, more preferably more than 70 wt. -%, preferably more than 80 wt. -%, preferably more than 90 wt. -%, preferably more than 95 wt. -%, based on the weight of 4,8, 11-dodecenal.

25. The composition according to any of the preceding claims 15 to 24, wherein the amount of (4E,8E) -dodec-4, 8, 11-trienol is less than 10 wt%, preferably less than 5 wt%, preferably less than 2 wt%, based on the weight of 4,8, 11-dodecenal.

26. The composition according to any one of the preceding claims 15 to 25, wherein the amount of (4Z,8Z) -dodec-4, 8, 11-trienol is less than 10 wt%, preferably less than 5 wt%, preferably less than 2 wt%, based on the weight of 4,8, 11-dodecenal.

27. The composition according to any one of the preceding claims 18 to 26, wherein said at least one solvent is selected from the group consisting of ethanol, isopropanol, diethylene glycol monoethyl ether, glycerol, propylene glycol, 1, 2-butanediol, dipropylene glycol, triethyl citrate and isopropyl myristate.

28. A composition according to any of the preceding claims 18 to 27, wherein said at least one deodorant active agent is selected from antiperspirants, esterase inhibitors and antibacterial agents.

29. A composition according to any one of claims 18 to 28 wherein the antiperspirant is selected from aluminium chloride, aluminium chlorohydrate (aluminium chlorohydrate), aluminium chlorohydrate (aluminium dichlorohydroxide), aluminium sesquichlorohydrate (aluminium seschloroxide), aluminium hydroxyallantoate (aluminium hydroxyallantoate), aluminium tartrate chloride (aluminium chlorohydrate), aluminium zirconium trihydroxide (aluminium zirconium chlorohydrate), zirconium tetrahydroxide (aluminium zirconium chlorohydrate) and aluminium zirconium pentachloride (aluminium zirconium chlorohydrate).

30. The composition according to any one of the preceding claims 18 to 28, wherein the esterase inhibitor is selected from the group consisting of trimethyl citrate, tripropyl citrate, triisopropyl citrate, tributyl citrate, triethyl citrate, lanosterol, cholesterol, campesterol, stigmasterol, sitosterol sulfate, sitosterol phosphate, glutaric acid, monoethyl glutarate, diethyl glutarate, adipic acid, monoethyl adipate, diethyl adipate, malonic acid, diethyl malonate, citric acid, malic acid, tartaric acid, diethyl tartrate and zinc glycinate.

31. The composition according to any one of the preceding claims 18 to 28, wherein the antibacterial agent is selected from the group consisting of chitosan, phenoxyethanol, 5-chloro-2- (2, 4-dichlorophenoxy) -phenol, 4-hydroxybenzoic acid and salts and esters thereof, N- (4-chlorophenyl) -N '- (3, 4-dichlorophenyl) -urea, 2,4,4' -trichloro-2 '-hydroxydiphenyl ether (triclosan), 4-chloro-3, 5-dimethylphenol, 2' -methylene-bis- (6-bromo-4-chlorophenol), 3-methyl-4- (1-methylethyl) -phenol, 2-benzyl-4-chlorophenol, 3- (4-chlorophenoxy) -propan-1, 2-diol, 3-iodo-2-propynyl butylcarbamate, chlorhexidine (chlorexidine), 3,4,4' -trichlorocarbanilide (TTC), phenoxyethanol, glycerol monocaprate, glycerol monocaprylate, Glycerol Monolaurate (GML), Diglycerol Monocaprate (DMC), salicylic acid-N-alkylamide.

32. The composition according to any one of the preceding claims 18 to 31, wherein the at least one surfactant is selected from anionic, nonionic, cationic, amphoteric and zwitterionic surfactants.

33. A composition according to any one of the preceding claims 18 to 32, wherein the at least one surfactant is an anionic surfactant.

34. The composition according to any one of the preceding claims, wherein the at least one antioxidant is selected from pentaerythritol, tetra-di-tert-butyl hydroxyhydrocinnamate, nordihydroguaiaretic acid, ferulic acid, resveratrol, propyl gallate, Butylhydroxytoluene (BHT), Butylhydroxyanisole (BHA), ascorbyl palmitate and tocopherols.

35. The composition according to any of the preceding claims 18 to 34, wherein the composition is selected from perfume compositions, body care compositions, hygiene articles, cleaning compositions, textile detergent compositions, compositions for dispensers, food products, food supplements, pharmaceutical compositions and crop protection compositions.

36. A method of imparting a clean scent to a composition comprising including 4,8,11-dodecatrienal into the composition.

37. A method of imparting a clean flax note to a composition comprising including 4,8,11-dodecatrienal into the composition.

38. A method of imparting citrus trim to a composition comprising including 4,8,11-dodecatrienal into the composition.

39. A method of imparting a marine character to a composition comprising including 4,8,11-dodecatrienal into the composition.

40. A method of imparting ozone tone to a composition comprising including 4,8,11-dodecatrienal into the composition.

41. A method of imparting cyclamen tone to a composition comprising including 4,8,11-dodecatrienal into the composition.

42. The process according to any one of claims 36 to 41, wherein 4,8, 11-dodecatrienol is used, comprising less than 0.2% by weight of 1,5,9-cyclododecatriene, based on the weight of 4,8, 11-dodecatrienol.

43. A process according to any one of claims 36 to 42, wherein a 4,8, 11-dodecatrienol is used comprising less than 0.1% by weight, preferably less than 0.05% by weight, of 1,5,9-cyclododecatriene, based on the weight of the 4,8, 11-dodecatrienol.

44. A method of imparting a fragrance impression to a composition comprising including 4,8,11-dodecatrienal free of 1,5,9-cyclododecatriene into the composition.

45. The method according to any one of claims 36 to 44, wherein the composition is selected from perfume compositions, body care compositions, hygiene articles, cleaning compositions, textile detergent compositions, compositions for dispensers, food products, food supplements, pharmaceutical compositions and crop protection compositions.

Detailed Description

Defining:

in the present invention, the term "aroma (aroma)" refers to sensory properties and comprises an odor (odor) and/or a flavor (flavour).

The term "aroma chemical" refers to a substance used to obtain an aroma impression (the term "aroma impression" is used herein interchangeably with the term "fragrance note") and encompasses its use for obtaining an olfactory (olfactory) and/or flavour (flavour) impression. The term "olfactory impression" refers to an odor impression without any positive or negative judgment, whereas the terms "scent impression" or "scent impression" (used interchangeably herein) are associated with a generally pleasant-feeling odor impression. Thus "fragrance" or "aroma" refers to an aromatic chemical that mainly induces a pleasant odor impression. Flavour refers to an aromatic chemical that elicits a taste impression.

The term "aroma profile" refers to the overall aroma impression of a fragrance chemical and consists of the individual aroma impressions of the fragrance chemical.

The term "fragrance composition" as used herein refers to a composition that induces fragrance. The term fragrance composition comprises "odour composition" and/or "flavour composition". An odor composition is a composition that mainly gives rise to an odor impression, and a flavor composition is a composition that mainly gives rise to a taste impression (taste impression).

The term odor composition comprises "fragrance compositions" or "aroma compositions" (used interchangeably herein) which mainly elicit a generally perceived pleasant odor impression.

The terms "compound" and "substance" are used synonymously throughout the present invention.

The term "refractory" describes the evaporation behavior of a fragrance chemical over time. The persistence can be determined, for example, by applying an aromatic chemical to a test strip and then olfactory evaluating the test strip for an odor impression. For fragrance chemicals with high persistence (tenacity), the time span over which the panelist can still recognize the fragrance impression is long.

The term "sustainability" describes the interaction of fragrance chemicals with a surface, such as skin or textiles, especially after subsequent treatment of the surface, such as washing. The tenacity can be measured, for example, by washing the textile with a textile detergent composition containing an aroma chemical and then olfactory evaluating the textile right after washing (wet textiles) and evaluating the dry textiles after long storage.

The term "stability" describes the behavior of a fragrance chemical when in contact with oxygen, light, and/or other substances. Fragrance chemicals with high stability retain their fragrance attributes for long periods of time, preferably in a wide variety of compositions and under a variety of storage conditions.

In order to impart a long-lasting fragrance impression to the composition or to a surface treated with the composition, the persistence, and the stability of the fragrance chemical in the composition should preferably be high.

4,8,11-dodecatrienal

The term "4, 8, 11-dodecatrienol" as used herein encompasses each individual isomer of 4,8, 11-dodecatrienol, which is (4E,8Z) -dodeca-4, 8, 11-trienol, (4Z,8E) -dodeca-4, 8, 11-trienol, (4E,8E) -dodeca-4, 8, 11-trienol, (4Z,4Z) -dodeca-4, 8, 11-trienol, and any mixture of two or more isomers.

In a preferred embodiment of the method, use and composition of the invention, the weight ratio of (4E,8Z) -dodec-4, 8, 11-trienol to (4Z,8E) -dodec-4, 8, 11-trienol is in the range of 1:1-2, preferably 1:1-1.5, more preferably 1: 1.1-1.3.

In a preferred embodiment of the method, use and composition of the invention, the amount of (4E,8Z) -dodec-4, 8, 11-trienol and (4Z,8E) -dodec-4, 8, 11-trienol is equal to or more than 50 wt%, preferably more than 60 wt%, more preferably more than 70 wt%, preferably more than 80 wt%, preferably more than 90 wt%, preferably more than 95 wt%, based on the weight of 4,8, 11-dodec-trienol.

In a preferred embodiment of the method, use and composition of the present invention, the amount of (4E,8E) -dodec-4, 8, 11-trienol is less than 10 wt%, preferably less than 5 wt%, preferably less than 2 wt%, based on the weight of 4,8, 11-dodec-trienol.

In a preferred embodiment of the method, use and composition of the invention, the amount of (4Z,8Z) -dodec-4, 8, 11-trienol is less than 10 wt%, preferably less than 5 wt%, preferably less than 2 wt%, based on the weight of 4,8, 11-dodecenal.

A preferred embodiment of the process, use and composition of the invention relates to 4,8,11-dodecatrienal comprising less than 0.2% by weight of 1,3, 5-cyclododecatriene, based on the weight of 4,8,11-dodecatrienal, preferably less than 0.1% by weight, more preferably less than 0.005% by weight of 1,3, 5-cyclododecatriene, based on the weight of 4,8, 11-dodecatrienal.

The term "weight of 4,8, 11-dodecatrienal" refers to the total amount of all isomers of 4,8, 11-dodecatrienal.

One embodiment of the methods, uses and compositions of the present invention relates to 4,8,11-dodecatrienal that does not comprise 1,3, 5-cyclododecatriene.

The 4,8,11-dodecatrienal can be prepared, for example, by obtaining the mixture described in examples 1 to 2 or examples 1 to 3 of WO 2010/086313 and further purifying the mixture thus obtained by methods known to those skilled in the art (e.g., distillation).

One embodiment of the present invention relates to the use of 4,8,11-dodecatrienal to impart a clean fragrance to a composition. A further embodiment relates to the use of 4,8,11-dodecatrienal to impart a flax note to the composition. A preferred embodiment relates to the use of 4,8,11-dodecatrienal to impart a clean flax note to the composition.

One embodiment of the present invention relates to the use of 4,8,11-dodecatrienal to impart citrus trim to a composition. One embodiment of the present invention therefore relates to the use of 4,8,11-dodecatrienal to impart marine touch to a composition. One embodiment of the present invention therefore relates to the use of 4,8,11-dodecatrienal to impart ozone tone to a composition. One embodiment of the present invention therefore relates to the use of 4,8,11-dodecatrienal for imparting cyclamen to a composition.

A preferred embodiment of the use as described above relates to the use of 4,8,11-dodecatrienal comprising less than 0.2% by weight of 1,5,9-cyclododecatriene, based on the weight of 4,8, 11-dodecatrienal. A preferred embodiment of the present invention relates to the use of 4,8, 11-dodecatrienol comprising less than 0.1 wt%, preferably less than 0.05 wt%, of 1,5,9-cyclododecatriene, based on the weight of 4,8, 11-dodecatrienol. One embodiment of the present invention relates to the use of 4,8,11-dodecatrienal which does not comprise 1,5, 9-cyclododecatriene.

One embodiment of the present invention relates to the use of 4,8, 11-dodecatrienol, which does not comprise 1,5,9-cyclododecatriene, as an aroma chemical, preferably as a perfume.

Composition comprising a metal oxide and a metal oxide

A further embodiment of the present invention relates to a composition comprising 4,8,11-dodecatrienal and at least one additional aroma chemical selected from the group consisting of:

geranyl acetate (3, 7-dimethyl-2, 6-octadien-1-yl acetate), alpha-hexyl cinnamic aldehyde, 2-phenoxyethyl isobutyrate (Phenylirat)¹) Dihydromyrcenol (2, 6-dimethyl-7-octen-2-ol), methyl dihydrojasmonate (preferably with greater than 60% by weight cis-jasmonate)Content of formula (a) (Hedione)⁹，Hedione HC⁹) 4,6,6,7,8, 8-hexamethyl-1, 3,4,6,7, 8-hexahydrocyclopenta [ g ] ring]Benzopyran (Galaxolid)³) Tetrahydrolinalool (3, 7-dimethyloctan-3-ol), ethyl linalool, benzyl salicylate, 2-methyl-3- (4-tert-butylphenyl) propanal (Lysmeral)²) Cinnamyl alcohol, 4, 7-methylene-3 a,4,5,6,7,7 a-hexahydro-5-indenyl acetate and/or 4, 7-methylene-3 a,4,5,6,7,7 a-hexahydro-6-indenyl acetate (Herbaflorat)¹) Citronellol, citronellyl acetate, tetrahydrogeraniol, vanillin, linalyl acetate, styryl acetate (1-phenylethyl acetate), octahydro-2, 3,8, 8-tetramethyl-2-naphthaleneacetone and/or 2-acetyl-1, 2,3,4,6,7, 8-octahydro-2, 3,8, 8-tetramethylnaphthalene (Iso E Super)³) Hexyl salicylate, 4-tert-butylcyclohexyl acetate (Orycone)¹) 2-tert-butylcyclohexyl acetate (Agrumex HC)¹) Alpha-ionone (4- (2,2, 6-trimethyl-2-cyclohexen-1-yl) -3-buten-2-one), n-alpha-methylionone, alpha-isomethylionone, coumarin, terpinyl acetate, 2-phenylethyl alcohol, 4- (4-hydroxy-4-methylpentyl) -3-cyclohexenecarbaldehyde (Lyral)³) Alpha-amyl cinnamic aldehyde, ethylene glycol brassylate, (E) -and/or (Z) -3-methylcyclopentadec-5-enone (Musconen)⁹) 15-pentadecyl-11-ene lactone and/or 15-pentadecyl-12-ene lactone (globalite)¹) 15-cyclopentadecanolide (Macrolide)¹) 1- (5,6,7, 8-tetrahydro-3, 5,5,6,8, 8-hexamethyl-2-naphthyl) ethanone (Tonalid)¹⁰) 2-isobutyl-4-methyltetrahydro-2H-pyran-4-ol (Florol)⁹) 2-Ethyl-4- (2,2, 3-trimethyl-3-cyclopenten-1-yl) -2-buten-1-ol (Sandolen)¹) Cis-3-hexenyl acetate, trans-2/cis-6-nonadienol, 2, 4-dimethyl-3-cyclohexenecarbaldehyde (Vertoctral)¹) 2,4,4, 7-tetramethyloct-6-en-3-one (Claritone)¹) 2, 6-dimethyl-5-hepten-1-al (Melonal)²) Borneol and 3- (3-isopropylphenyl) butyraldehyde (Florhdral)²) 2-methyl-3- (3, 4-methylenedioxyphenyl) propanal (Helinal)³) 3- (4-ethylphenyl) -2, 2-dimethylpropionaldehyde (Florazon)¹) 7-methyl-2H-1, 5-benzodioxepin-3(4H) -one (Calone), acetic acid 3,3, 5-trimethylcyclohexaneAn ester (preferably having a cis isomer content of 70% by weight or more), 2,5, 5-trimethyl-1, 2,3,4,4a,5,6, 7-octahydronaphthalen-2-ol (Ambrinol S)¹) 3- (4-tert-butylphenyl) -propionaldehyde (Bourgeonal)⁴) 2-Methylpentanoic acid ethyl ester (Manzanate)⁴) Ethoxy methoxycyclododecane (Amberwood)¹) 2, 4-dimethyl-4, 4a,5,9 b-tetrahydroindeno [1,2-d ]][1,3]Dioxines (Magnolan)¹) 2-tert-butylcyclohexyl acetate (Verdox)³) And 3- [5,5, 6-trimethylbicyclo [2.2.1 ]]Hept-2-yl]Cyclohexan-1-ol (Sandela)⁴)。

When trade names are given above, these refer to the following sources:

¹trade name of Symrise GmbH, Germany;²trade name of BASF SE;³International Flavors&trade names of fragrans inc., USA;⁴Givaudan AG,Switzerland；⁹firmenich s.a., trade name of Switzerland;¹⁰PFW Aroma Chemicals B.V., tradename of the Netherlands.

A preferred embodiment of the present invention relates to a composition comprising 4,8,11-dodecatrienal and at least one additional aromatic chemical selected from the group consisting of methyl benzoate, benzyl acetate, geranyl acetate, 2-isobutyl-4-methyltetrahydro-2H-pyran-4-ol, linalool, 2-isobutyl-4-methyltetrahydro-2H-pyran-4-ol, and methyl benzoate.

A preferred embodiment of the present invention relates to a composition comprising 4,8,11-dodecatrienal and at least one additional aroma chemical selected from the group consisting of ethyl vanillin, 2, 5-dimethyl-4-hydroxy-2H-furan-3-one (furaneol) or 3-hydroxy-2-methyl-4H-pyran-4-one (maltol).

Additional Fragrance Chemicals with which 4,8,11-dodecatrienal can be combined to produce compositions according to the present invention can be found, for example, in s.arctander, Perfume and Flavor Chemicals, vol.i and II, montcalair, n.j.,1969, self-published or k.bauer, d.garbe and h.surburg, Common Fragrance and Flavor Materials, 4 th edition, Wiley-VCH, Weinheim 2001. Specifically, mention may be made of:

extracts from natural raw materials, such as essential oils, condensables, absolutes, resins, balms, tinctures, e.g. essential oils, balms, tinctures, etc

Ambergris tincture; fragrant tree oil; angelica seed oil; angelica root oil; anise oil; valerian oil; basil oil; cleaning tree moss with oil; laurel oil; mugwort oil; benzoin resin; bergamot oil; beeswax absolute; birch tar oil; bitter almond oil; parsley oil; leaf oil of Bu Ku Ye; sandalwood oil of Brazil; juniper tar; calamus oil; camphor oil; cananga oil; cardamom oil; kailu oil; cinnamon oil; cinnamon absolute oil; castor oil; cedar leaf oil; cedar wood oil; cistus oil; citronella oil; lemon oil; copaiba balsam; copaiba balsam oil; coriander oil; wood vetch root oil; cumin oil; cypress oil; artemisia annua oil; dill leaf oil; dill seed oil; vanilla absolute (Eau de brouts absolute); cleaning oak moss oil; elemi oil; tarragon oil; lemon eucalyptus oil; eucalyptus oil; fennel oil; pine needle oil; white rosin oil; white rosin resin; geranium oil; grapefruit oil; guaiac oil; gule-rue-fat; oil of crura oil; purifying the helichrysum oil; helichrysum oil; ginger oil; iris root neat oil; orris root oil; jasmine absolute oil; sweet flag oil; chamomile oil; roman chamomile oil; carrot seed oil; kailu oil; pine needle oil; spearmint oil; oil of Artemisia vulgaris; labdanum oil; labdanum essential oil; a Liberbant resin; the lavender absolute oil is striking; lavender oil with eye-catching effect; lavender absolute oil; lavender oil; lemon grass oil; angelica oil; distilling lime oil; squeezing lime oil; linalool oil; litsea cubeba oil; laurel leaf oil; nutmeg oil; marjoram oil; orange oil; sweet osmanthus oil; mimosa absolute; musk seed oil; musk tincture; clary sage oil; nutmeg oil; purifying Myrrha with oil; myrrh oil; myrtle oil; clove leaf oil; clove flower oil; neroli oil; purifying Olibanum oil; mastic oil; hongyun medicinal oil; neroli absolute; orange oil; oregano oil; palmarosa oil; patchouli oil; perilla seed oil; mulu fragrant oil; parsley leaf oil; parsley seed oil; bitter orange leaf oil; peppermint oil; pepper oil; allspice oil; pine oil; peppermint oil; rose absolute oil; rosewood oil; rose oil; rosemary oil; sage oil; spanish sage oil; sandalwood oil; celery seed oil; lavender oil; anise oil; storax oil; marigold oil; fir leaf oil; tea tree oil; turpentine oil; thyme oil; tulu balsam; extracting semen Phaseoli vulgaris; tuberose absolute oil; a vanilla extract; violet leaf absolute oil; verbena oil; vetiver oil; juniper berry oil; wine residue oil; wormwood oil; wintergreen oil; hyssop oil; musk cat essential oil; cinnamon leaf oil; cinnamon bark oil, and fractions thereof, or fractions isolated therefrom;

individual essences selected from hydrocarbons, such as 3-carene; alpha-pinene; beta-pinene; alpha-terpinene; gamma-terpinene; p-cymene; bisabolene; camphene; caryophyllene; cedrene; a farnesene; limonene; longifolene; myrcene; ocimene; valencene; (E, Z) -1,3, 5-undecatriene; styrene; diphenylmethane;

aliphatic alcohols such as hexanol; octanol; 3-octanol; 2, 6-dimethylheptanol; 2-methyl-2-heptanol; 2-methyl-2-octanol; (E) -2-hexenol; (E) -and (Z) -3-hexenol; 1-octen-3-ol; a mixture of 3,4,5,6, 6-pentamethyl-3/4-hepten-2-ol and 3,5,6, 6-tetramethyl-4-methylenehept-2-ol; (E, Z) -2, 6-nonadienol; 3, 7-dimethyl-7-methoxyoct-2-ol; 9-decenol; 10-undecenol; 4-methyl-3-decen-5-ol;

aliphatic aldehydes and acetals thereof, such as hexanal; heptanal; octanal; nonanal; decanal; undecalaldehyde; dodecanal; tridecanal; 2-methyl octanal; 2-methylnonanal; (E) -2-hexenal; (Z) -4-heptenal; 2, 6-dimethyl-5-heptenal; 10-undecenal; (E) -4-decenal; 2-dodecenal; 2,6, 10-trimethyl-9-undecenal; 2,6, 10-trimethyl-5, 9-undecadinaldehyde; heptanal diethyl acetal (heptanal diethyl acetal); 1, 1-dimethoxy-2, 2, 5-trimethyl-4-hexene; citronellyloxyacetaldehyde; (E/Z) -1- (1-methoxypropoxy) -hex-3-ene; aliphatic ketones and oximes thereof, such as 2-heptanone; 2-octanone; 3-octanone; 2-nonanone; 5-methyl-3-heptanone; 5-methyl-3-heptanone oxime; 2,4,4, 7-tetramethyl-6-octen-3-one; 6-methyl-5-hepten-2-one;

aliphatic sulfur-containing compounds such as 3-methylthiohexanol; 3-methylthiohexanol acetate; 3-mercaptohexanol; 3-mercaptohexanol acetate; 3-mercaptohexanol butyrate; 3-acetylthio hexanol acetate; 1-menthene-8-thiol;

aliphatic nitriles such as 2-nonenenitrile; 2-undecenenitrile; 2-tridecene carbonitrile; 3, 12-tridecadienylnitrile; 3, 7-dimethyl-2, 6-octadienenitrile; 3, 7-dimethyl-6-octenenitrile;

esters of aliphatic carboxylic acids, such as (E) -and (Z) -3-hexenyl formate; ethyl acetoacetate; isoamyl acetate; hexyl acetate; 3,5, 5-trimethylhexyl acetate; 3-methyl-2-butenyl acetate; 2-hexenyl (E) -acetate; acetic acid (E) -and (Z) -3-hexenyl ester; octyl acetate; 3-octyl acetate; 1-octen-3-yl acetate; ethyl butyrate; butyl butyrate; isoamyl butyrate; hexyl butyrate; (E) -and (Z) -3-hexenyl isobutyrate; hexyl crotonate; ethyl isovalerate; 2-methyl pentanoic acid ethyl ester; ethyl caproate; allyl caproate; ethyl heptanoate; allyl heptanoate; ethyl octanoate; (E, Z) -2, 4-decadienoic acid ethyl ester; methyl 2-octynoate (methyl 2-octinate); methyl 2-nonynoate (methyl 2-nononate); 2-isopentyloxy-allyl acetate; methyl-3, 7-dimethyl-2, 6-octadienoate; 4-methyl-2-pentyl crotonate;

acyclic terpene alcohols such as geraniol; nerol; linalool; lavender alcohol; nerolidol; farnesol; tetrahydrolinalool; 2, 6-dimethyl-7-octen-2-ol; 2, 6-dimethyloctan-2-ol; 2-methyl-6-methylene-7-octen-2-ol; 2, 6-dimethyl-5, 7-octadien-2-ol; 2, 6-dimethyl-3, 5-octadien-2-ol; 3, 7-dimethyl-4, 6-octadien-3-ol; 3, 7-dimethyl-1, 5, 7-octatrien-3-ol; 2, 6-dimethyl-2, 5, 7-octatrien-1-ol; and their formates, acetates, propionates, isobutyrates, butyrates, isovalerates, valerates, caproates, crotonates, tiglates (tiglinites) and 3-methyl-2-butenoate;

acyclic terpene aldehydes and ketones, such as geranial; neral; citronellal; 7-hydroxy-3, 7-dimethyloctanal; 7-methoxy-3, 7-dimethyloctanal; 2,6, 10-trimethyl-9-undecenal; geranylacetone; and the dimethyl-and diethyl acetals of geranial, neral, 7-hydroxy-3, 7-dimethyloctanal; cyclic terpene alcohols such as menthol; isopulegol; alpha-terpineol; terpin-4-ol; menthol-8-ol; menthol-1-ol; menthol-7-ol; borneol; isoborneol; linalool oxide; nopol; cedrol; ambroxol (ambrinol); vetiverol; guaiol; and their formates, acetates, propionates, isobutyrates, butyrates, isovalerates, valerates, caproates, crotonates, tiglates (tiglinites) and 3-methyl-2-butenoate;

cyclic terpene aldehydes and ketones, such as menthone; isomenthone; 8-mercaptomenth-3-one; carvone; camphor; fenchone; alpha-ionone; beta-ionone; alpha-n-methyl ionone; beta-n-methyl ionone; alpha-isomethylionone; beta-isomethylionone; α -irone; alpha-damascone; beta-damascone; beta-damascenone; delta-damascone; gamma-damascone; 1- (2,4, 4-trimethyl-2-cyclohexen-1-yl) -2-buten-1-one; 1,3,4,6,7,8 a-hexahydro-1, 1,5, 5-tetramethyl-2H-2, 4 a-methanonaphthalen-8 (5H) -one; 2-methyl-4- (2,6, 6-trimethyl-1-cyclohexen-1-yl) -2-butenal; nootkatone; dihydronootkatone; 4,6, 8-megastigmatrienol-3-one; alpha-citral; beta-citral; acetylated cedarwood oil (methyl cedryl ketone);

cyclic alcohols, such as 4-tert-butylcyclohexanol; 3,3, 5-trimethylcyclohexanol; 3-isobornyl cyclohexanol; 2,6, 9-trimethyl-Z2, Z5, E9-cyclododecatrien-1-ol; 2-isobutyl-4-methyltetrahydro-2H-pyran-4-ol;

alicyclic alcohols such as α -3, 3-trimethylcyclohexylmethanol; 1- (4-isopropylcyclohexyl) ethanol; 2-methyl-4- (2,2, 3-trimethyl-3-cyclopent-1-yl) butanol; 2-methyl-4- (2,2, 3-trimethyl-3-cyclopent-1-yl) -2-buten-1-ol; 2-ethyl-4- (2,2, 3-trimethyl-3-cyclopent-1-yl) -2-buten-1-ol; 3-methyl-5- (2,2, 3-trimethyl-3-cyclopent-1-yl) pentan-2-ol; 3-methyl-5- (2,2, 3-trimethyl-3-cyclopent-1-yl) -4-penten-2-ol; 3, 3-dimethyl-5- (2,2, 3-trimethyl-3-cyclopent-1-yl) -4-penten-2-ol; 1- (2,2, 6-trimethylcyclohexyl) pentan-3-ol; 1- (2,2, 6-trimethylcyclohexyl) hex-3-ol;

cyclic and alicyclic ethers such as eucalyptol (cineol); cedar methyl ether; cyclododecyl methyl ether; 1, 1-dimethoxycyclododecane; (ethoxymethoxy) cyclododecane; alpha-epoxy cedrane; 3a,6,6,9 a-tetramethyldodecahydronaphtho [2,1-b ] furan; 3 a-ethyl-6, 6,9 a-trimethyldodecahydronaphtho [2,1-b ] furan; 1,5, 9-trimethyl-13-oxabicyclo- [10.1.0] tridec-4, 8-diene; rose oxide; 2- (2, 4-dimethyl-3-cyclohexen-1-yl) -5-methyl-5- (1-methylpropyl) -1, 3-dioxane;

cyclic and macrocyclic ketones, such as 4-tert-butylcyclohexanone; 2,2, 5-trimethyl-5-pentylcyclopentanone; 2-heptyl cyclopentanone; 2-pentylcyclopentanone; 2-hydroxy-3-methyl-2-cyclopenten-1-one; 3-methyl-cis-2-penten-1-yl-2-cyclopenten-1-one; 3-methyl-2-pentyl-2-cyclopenten-1-one; 3-methyl-4-cyclopentadecanone; 3-methyl-5-cyclopentadecanone; 3-methylcyclopentadecanone; 4- (1-ethoxyvinyl) -3,3,5, 5-tetramethylcyclohexanone; 4-tert-amylcyclohexanone; 5-cyclohexadecen-1-one; 6, 7-dihydro-1, 1,2,3, 3-pentamethyl-4 (5H) -indanone; 8-cyclohexadecen-1-one; 7-cyclohexadecen-1-one; (7/8) -cyclohexadecen-1-one; 9-cyclopentadecen-1-one; cyclopentadecanone; (ii) cyclohexadecanone;

alicyclic aldehydes such as 2, 4-dimethyl-3-cyclohexenecarbaldehyde; 2-methyl-4- (2,2, 6-trimethylcyclohexen-1-yl) -2-butenal; 4- (4-hydroxy-4-methylpentyl) -3-cyclohexenecarbaldehyde; 4- (4-methyl-3-penten-1-yl) -3-cyclohexenecarbaldehyde;

alicyclic ketones such as 1- (3, 3-dimethylcyclohexyl) -4-penten-1-one; 2, 2-dimethyl-1- (2, 4-dimethyl-3-cyclohexen-1-yl) -1-propanone; 1- (5, 5-dimethyl-1-cyclohexen-1-yl) -4-penten-1-one; 2,3,8, 8-tetramethyl-1, 2,3,4,5,6,7, 8-octahydro-2-naphthylmethylketone; methyl 2,6, 10-trimethyl-2, 5, 9-cyclododecatrienyl ketone; tert-butyl (2, 4-dimethyl-3-cyclohexen-1-yl) ketone;

esters of cyclic alcohols, such as 2-tert-butylcyclohexyl acetate; 4-tert-butylcyclohexyl acetate; 2-tert-amylcyclohexyl acetate; 4-tert-amylcyclohexyl acetate; 3,3, 5-trimethylcyclohexyl acetate; decahydro-2-naphthyl acetate; 2-cyclopentylcyclopentyl crotonate; acetic acid 3-pentyltetrahydro-2H-pyran-4-yl ester; decahydro-2, 5,5,8 a-tetramethyl-2-naphthyl acetate; acetic acid 4, 7-methylene-3 a,4,5,6,7,7 a-hexahydro-5 or 6-indenyl ester; propionic acid 4, 7-methylene-3 a,4,5,6,7,7 a-hexahydro-5 or 6-indenyl ester; 4, 7-methylene-3 a,4,5,6,7,7 a-hexahydro-5 or 6-indenyl isobutyrate; acetic acid 4, 7-methyleneoctahydro-5 or 6-indenyl ester;

esters of alicyclic alcohols, such as 1-cyclohexylethyl crotonate;

esters of alicyclic carboxylic acids such as allyl 3-cyclohexylpropionate; cyclohexyloxy allyl acetate; cis-and trans-methyl dihydrojasmonate; cis-and trans-jasmonic acid methyl ester; 2-hexyl-3-oxocyclopentanecarboxylic acid methyl ester; 2-ethyl-6, 6-dimethyl-2-cyclohexenecarboxylic acid ethyl ester; ethyl 2,3,6, 6-tetramethyl-2-cyclohexenecarboxylate; 2-methyl-1, 3-dioxolane-2-acetic acid ethyl ester;

araliphatic alcohols, such as benzyl alcohol; 1-phenylethyl alcohol, 2-phenylethyl alcohol, 3-phenylpropanol; 2-phenyl propanol; 2-phenoxyethanol; 2, 2-dimethyl-3-phenylpropanol; 2, 2-dimethyl-3- (3-methylphenyl) propanol; 1, 1-dimethyl-2-phenylethyl alcohol; 1, 1-dimethyl-3-phenylpropanol; 1-ethyl-1-methyl-3-phenylpropanol; 2-methyl-5-phenylpentanol; 3-methyl-5-phenylpentanol; 3-phenyl-2-propen-1-ol; 4-methoxybenzyl alcohol; 1- (4-isopropylphenyl) ethanol;

esters of araliphatic alcohols and aliphatic carboxylic acids, for example benzyl acetate; benzyl propionate; benzyl isobutyrate; benzyl isovalerate; 2-phenylethyl acetate; 2-phenylethyl propionate; 2-phenylethyl isobutyrate; isovaleric acid 2-phenylethyl ester; 1-phenylethyl acetate; acetic acid alpha-trichloromethyl benzyl ester; acetic acid alpha, alpha-dimethylphenylethyl ester; butyric acid α, α -dimethylphenylethyl ester; cinnamyl acetate; 2-phenoxyethyl isobutyrate; 4-methoxybenzyl acetate;

araliphatic ethers, such as 2-phenylethylmethyl ether; 2-phenethylisoamyl ether; 2-phenethyl 1-ethoxyethyl ether; phenylacetaldehyde dimethyl acetal; phenylacetaldehyde diethyl acetal; hydratropic aldehyde dimethyl acetal (hydratropic aldehyde dimethyl acetate); phenylacetaldehyde glycerol acetal; 2,4, 6-trimethyl-4-phenyl-1, 3-dioxane; 4,4a,5,9 b-tetrahydroindeno [1,2-d ] -m-dioxine; 4,4a,5,9 b-tetrahydro-2, 4-dimethylindeno [1,2-d ] -m-dioxin;

aromatic and araliphatic aldehydes, such as benzaldehyde; phenyl acetaldehyde; 3-phenylpropionaldehyde; hydratropic aldehyde (hydratropic aldehyde); 4-methylbenzaldehyde; 4-methylphenylacetal; 3- (4-ethylphenyl) -2, 2-dimethylpropanal; 2-methyl-3- (4-isopropylphenyl) propanal; 2-methyl-3- (4-tert-butylphenyl) propanal; 2-methyl-3- (4-isobutylphenyl) propanal; 3- (4-tert-butylphenyl) propanal; cinnamic aldehyde; alpha-butylcinnamaldehyde; alpha-amyl cinnamic aldehyde; alpha-hexyl cinnamic aldehyde; 3-methyl-5-phenylpentanal; 4-methoxybenzaldehyde; 4-hydroxy-3-methoxybenzaldehyde; 4-hydroxy-3-ethoxybenzaldehyde; 3, 4-methylenedioxybenzaldehyde; 3, 4-dimethoxybenzaldehyde; 2-methyl-3- (4-methoxyphenyl) propanal; 2-methyl-3- (4-methylenedioxyphenyl) propanal;

aromatic and araliphatic ketones, for example acetophenone; 4-methylacetophenone; 4-methoxyacetophenone; 4-tert-butyl-2, 6-dimethylacetophenone; 4-phenyl-2-butanone; 4- (4-hydroxyphenyl) -2-butanone; 1- (2-naphthyl) ethanone; 2-benzofuranylethanone; (3-methyl-2-benzofuranyl) ethanone; benzophenone; 1,1,2,3,3, 6-hexamethyl-5-indanylmethyl ketone; 6-tert-butyl-1, 1-dimethyl-4-indanylmethyl ketone; 1- [2, 3-dihydro-1, 1,2, 6-tetramethyl-3- (1-methylethyl) -1H-5-indenyl ] ethanone; 5 ', 6', 7 ', 8' -tetrahydro-3 ', 5', 5 ', 6', 8 ', 8' -hexamethyl-2-naphthalenone;

aromatic and araliphatic carboxylic acids and esters thereof, for example benzoic acid; phenylacetic acid; methyl benzoate; ethyl benzoate; hexyl benzoate; benzyl benzoate; methyl phenylacetate; ethyl phenylacetate; geranyl phenylacetate; phenyl ethyl phenylacetate; methyl cinnamate; ethyl cinnamate; cinnamic acid benzyl ester; cinnamic acid phenethyl ester; cinnamic acid cinnamyl ester; allyl phenoxyacetate; methyl salicylate; isoamyl salicylate; hexyl salicylate; cyclohexyl salicylate; cis-3-hexenyl salicylate; benzyl salicylate; phenethyl salicylate; methyl 2, 4-dihydroxy-3, 6-dimethylbenzoate; 3-phenylglycidic acid ethyl ester; 3-methyl-3-phenylglycidic acid ethyl ester;

nitrogen-containing aromatic compounds, such as 2,4, 6-trinitro-1, 3-dimethyl-5-tert-butylbenzene; 3, 5-dinitro-2, 6-dimethyl-4-tert-butyl acetophenone; cinnamonitrile; 3-methyl-5-phenyl-2-valeronitrile; 3-methyl-5-phenylpentanenitrile; methyl anthranilate; methyl N-methyl anthranilate; schiff base of methyl anthranilate and 7-hydroxy-3, 7-dimethyloctanal, 2-methyl-3- (4-tert-butylphenyl) propanal or 2, 4-dimethyl-3-cyclohexenecarbaldehyde; 6-isopropylquinoline; 6-isobutylquinoline; 6-sec-butylquinoline; 2- (3-phenylpropyl) pyridine; indole; skatole; 2-methoxy-3-isopropylpyrazine; 2-isobutyl-3-methoxypyrazine;

phenols, phenyl ethers and phenyl esters, such as estragole; anethole; eugenol; eugenyl methyl ether; isoeugenol; isobutoxy methyl ether; thymol; carvacrol; diphenyl ether; beta-naphthylmethyl ether; beta-naphthylethyl ether; β -naphthyl isobutyl ether; 1, 4-dimethoxybenzene; eugenol acetate; 2-methoxy-4-methylphenol; 2-ethoxy-5- (1-propenyl) phenol; p-cresol phenylacetate;

heterocyclic compounds, such as 2, 5-dimethyl-4-hydroxy-2H-furan-3-one; 2-ethyl-4-hydroxy-5-methyl-2H-furan-3-one; 3-hydroxy-2-methyl-4H-pyran-4-one; 2-ethyl-3-hydroxy-4H-pyran-4-one;

lactones, such as 1, 4-octalactone (octalactone); 3-methyl-1, 4-octalactone; 1, 4-nonalactone; 1, 4-decalactone; 8-decan-1, 4-lactone; 1, 4-undecalactone; 1, 4-dodecalactone; 1, 5-decalactone; 1, 5-dodecalactone; 4-methyl-1, 4-decalactone; 1, 15-pentadecanolide; cis-and trans-11-pentadecen-1, 15-olides; cis-and trans-12-pentadecen-1, 15-olides; 1, 16-hexadecanolide; 9-hexadecen-1, 16-lactone; 10-oxa-1, 16-hexadecanolide; 11-oxa-1, 16-hexadecanolide; 12-oxa-1, 16-hexadecanolide; 1, 12-dodecanedioic acid ethylene glycol ester; 1, 13-tridecanedioic acid ethylene glycol ester; coumarin; 2, 3-dihydrocoumarin; octahydro coumarin.

A further embodiment of the present invention relates to a composition comprising 4,8,11-dodecatrienal and at least one additional component selected from the group consisting of an oil component, an antioxidant, a deodorant active, and a solvent.

One embodiment of the present invention is therefore directed to a composition comprising 4,8,11-dodecatrienal and at least one solvent.

In the present invention, the "solvent" is used to dilute the 4,8,11-dodecatrienal used according to the invention and/or any other component of the composition without its own aroma.

The one or more solvents may be present in the composition from 0.01 to 99% by weight of the composition. In a preferred embodiment of the invention, the composition comprises from 0.1 to 90 wt.%, preferably from 0.5 to 80 wt.%, of solvent, based on the total weight of the composition. The amount of solvent may be selected according to the composition. In one embodiment of the invention, the composition comprises 0.05 to 10 wt. -%, preferably 0.1 to 5 wt. -%, more preferably 0.2 to 3 wt. -% of solvent based on the total weight of the composition. In one embodiment of the invention, the composition comprises 20 to 70 wt.%, preferably 25 to 50 wt.%, of solvent based on the total weight of the composition.

Preferred solvents are ethanol, dipropylene glycol (DPG), propylene glycol, 1, 2-butanediol, glycerol, diethylene glycol monoethyl ether, diethyl phthalate (DEP), isopropyl myristate (IPM), triethyl citrate (TEC) and Benzyl Benzoate (BB).

Particularly preferred solvents are selected from the group consisting of ethanol, propylene glycol, dipropylene glycol, triethyl citrate, benzyl benzoate, and isopropyl myristate.

In a preferred embodiment of the invention, the solvent is selected from the group consisting of ethanol, isopropanol, diethylene glycol monoethyl ether, glycerol, propylene glycol, 1, 2-butanediol, dipropylene glycol, triethyl citrate and isopropyl myristate.

One embodiment of the present invention is therefore directed to a composition comprising 4,8,11-dodecatrienal and at least one oil component.

The oil component is typically present in an amount of from 0.1 to 80 wt.%, preferably from 0.5 to 70 wt.%, more preferably from 1 to 60 wt.%, even more preferably from 1 to 50 wt.%, particularly from 1 to 40 wt.%, more particularly from 5 to 25 wt.%, especially from 5 to 15 wt.%, based on the total weight of the composition.

The oil component can be chosen, for example, from Guerbet alcohols based on fatty alcohols containing from 6 to 18, preferably from 8 to 10, carbon atoms, and also other additional esters, such as myristyl myristate, myristyl palmitate, myristyl stearate, myristyl isostearate, myristyl oleate, behenyl behenateMyristyl behenate, myristyl erucate, cetyl myristate, cetyl palmitate, cetyl stearate, cetyl isostearate, cetyl oleate, cetyl behenate, cetyl erucate, stearyl myristate, stearyl palmitate, stearyl stearate, stearyl isostearate, stearyl oleate, stearyl behenate, stearyl erucate, isostearyl myristate, isostearyl palmitate, isostearyl stearate, isostearyl isostearate, isostearyl oleate, isostearyl behenate, isostearyl oleate, oleyl myristate, isostearyl palmitate, isostearyl stearate, isostearyl isostearate, isostearyl oleate, isostearyl behenate, isostearyl oleate, oleyl myristate, oleyl palmitate, oleyl stearate, isostearyl oleate, oleyl behenate, oleyl erucate, erucyl oleate, didodecyl myristate, Behenyl palmitate, behenyl stearate, behenyl erucate didodecyl oleate, erucic acid didodecyl myristate, erucyl palmitate, erucyl stearate, erucyl isostearate, erucyl oleate, erucyl behenyl behenate, erucyl oleate, erucyl behenate, and erucyl erucate. Also suitable are C₁₈-C₃₈Alkyl-hydroxycarboxylic acids with linear or branched C₆-C₂₂Esters of fatty alcohols, more particularly dioctyl malate, esters of linear and/or branched fatty acids with polyols (e.g. propylene glycol, dimer diol or trimer triol), based on C₆-C₁₀Triglycerides of fatty acids, based on C₆-C₁₈Liquid mono-, di-and triglyceride mixtures of fatty acids, C₆-C₂₂Esters of aliphatic and/or Guerbet alcohols with aromatic carboxylic acids, more particularly benzoic acid, dicarboxylic acids with polyols containing 2 to 10 carbon atoms and 2 to 6 hydroxyl groups, vegetable oils, branched-chain primary alcohols, substituted cyclohexanes, linear and branched C₆-C₂₂Aliphatic alcohol carbonates, e.g. dioctyl carbonate (CCC) based on fats containing from 6 to 18, preferably from 8 to 10, carbon atomsGuerbet carbonates of alcohols, benzoic acids and linear and/or branched C₆To C₂₂Esters of alcohols (e.g. of alcohols)TN), linear or branched, symmetrical or asymmetrical dialkyl ethers having from 6 to 22 carbon atoms per alkyl radical, e.g. dioctyl ether(s) ((s)OE), ring opening products of epoxidized fatty acid esters with polyols and hydrocarbons, or mixtures thereof.

One embodiment of the present invention is therefore directed to a composition comprising 4,8,11-dodecatrienal and at least one antioxidant.

Antioxidants can inhibit or prevent undesirable changes in the protected composition caused by the oxygen effect and other oxidative processes. Antioxidants function in most cases in that they act as radical scavengers for the radicals generated during autoxidation.

The antioxidant may, for example, be selected from

Amino acids (e.g. glycine, alanine, arginine, serine, threonine, histidine, tyrosine, tryptophan) and derivatives thereof,

imidazole (e.g. urocanic acid) and derivatives thereof,

peptides, such as D, L-carnosine, D-carnosine, L-carnosine (═ β -alanyl-L-histidine), and derivatives thereof,

carotenoids, carotenes (e.g. alpha-carotene, beta-carotene, lycopene, lutein) or derivatives thereof,

-chlorogenic acid and its derivatives,

lipoic acid and derivatives thereof (e.g. dihydrolipoic acid),

aurothioglucose, propylthiouracil and other thiols (e.g.thioredoxin, glutathione, cysteine, cystine, cystamine and their glycosyl groups, N-acetyl, methyl, ethyl, propyl, pentyl, butyl and dodecyl, palmitoyl, oleoyl, gamma-linoleoyl, cholesteryl and glyceryl esters) and their salts,

dilauryl thiodipropionate, distearyl thiodipropionate, thiodipropionate and its derivatives (esters, ethers, peptides, lipids, nucleotides, nucleosides and salts),

sulfoximine compounds (e.g. buthionine sulfoximine, homocysteine sulfoximine, buthionine sulfone, penta-, hexa-, hepta-thionine sulfoximine),

- (metal) chelating agents (e.g. alpha-hydroxy fatty acids, palmitic acid, phytic acid, lactoferrin),

-alpha-hydroxy acids (e.g. citric acid, lactic acid, malic acid),

humic acid, bile extract, bilirubin, biliverdin, boldin (alkaloid from the plant bourdon tree (Peumus boldus), boldo extract),

-EDTA, EGTA and derivatives thereof,

unsaturated fatty acids and derivatives thereof (e.g. gamma-linolenic acid, linoleic acid, oleic acid),

-folic acid and derivatives thereof,

ubiquinone and ubiquinol and derivatives thereof,

vitamin C and derivatives (e.g. ascorbyl palmitate, magnesium ascorbyl phosphate, ascorbyl acetate),

tocopherols and derivatives (e.g. vitamin E acetate),

vitamin A and derivatives (vitamin A palmitate),

coniferyl benzoate of benzoin gum, rutinic acid (rutic acid) and its derivatives, alpha-glycosyl rutin, ferulic acid, furfurylidene glucitol,

butylhydroxytoluene (BHT), Butylhydroxyanisole (BHA),

nordihydroguaiaretic acid, trihydroxyphenylbutanone, uric acid and derivatives thereof, mannose and derivatives thereof,

-a superoxide dismutase (SOD),

zinc and its derivatives (e.g. ZnO, ZnSO)₄)，

Selenium and its derivatives (e.g. selenium methionine) and

stilbene and its derivatives (for example stilbene oxide, trans-stilbene oxide).

In a preferred embodiment, the antioxidant is selected from pentaerythritol, tetra-di-tert-butyl hydroxyhydrocinnamate, nordihydroguaiaretic acid, ferulic acid, resveratrol, propyl gallate, Butylhydroxytoluene (BHT), Butylhydroxyanisole (BHA), ascorbyl palmitate, and tocopherol.

The composition according to the invention may comprise an antioxidant in an amount of from 0.001 to 25 wt. -%, preferably from 0.005 to 10 wt. -%, preferably from 0.01 to 8 wt. -%, preferably from 0.025 to 7 wt. -%, preferably from 0.05 to 5 wt. -%, based on the total weight of the composition.

The 4,8,11-dodecatrienal according to the invention can preferably be used to impart clean, long-lasting notes to deodorant compositions and to the skin treated with such compositions.

Deodorant compositions (deodorants and antiperspirants) combat, mask or eliminate body malodors. The formation of body odour is caused by the action of skin bacteria on apocrine sweat which results in the formation of unpleasant odour degradation products.

One embodiment of the present invention is therefore directed to a composition comprising 4,8,11-dodecatrienal and at least one deodorant active.

In a preferred embodiment of the present invention, the at least one deodorant active agent is selected from antiperspirants, esterase inhibitors and antibacterial agents.

Suitable antiperspirants may be selected from salts of aluminium, zirconium or zinc. Examples are aluminum chloride, aluminum chlorohydrate (aluminum chlorohydrate), aluminum chlorohydrate (aluminum dichlorohydroate), aluminum sesquichlorohydrate (aluminum sesquichlorohydrate), and complexes thereof with, for example, 1, 2-propanediol, aluminum hydroxyallantoate (aluminum hydroxyallantoate), aluminum tartrate chloride, aluminum zirconium chlorohydrate, aluminum zirconium tetrachloroate, aluminum zirconium pentachloride, and complexes thereof with, for example, amino acids, such as glycine. Aluminum chlorohydrate, tetrachloroaluminum zirconium hydroxide, pentachlorinated aluminum zirconium hydroxide and complexes thereof are preferably used.

In a preferred embodiment of the invention, the composition comprises at least one antiperspirant selected from the group consisting of aluminum chloride, aluminum chlorohydrate (aluminum chlorohydrate), aluminum dichloroate (aluminum dichloroate), aluminum sesquichlorohydrate (aluminum sesquichlorohydrate), aluminum hydroxyallantoate (aluminum hydroxyallantoate), aluminum tartrate chloride, aluminum zirconium chlorohydrate, aluminum zirconium tetrachloroate, and aluminum zirconium pentachlorohydrite.

The compositions according to the invention may comprise antiperspirant in an amount of from 1 to 50, preferably from 5 to 30, more particularly from 10 to 25% by weight, based on the solids content of the composition.

In the case of sweating in the axillary region, extracellular enzyme-esterases, mainly proteases and/or lipases, are formed by the bacteria and cleave the esters present in the sweat, in the course of which odors are released. Suitable esterase inhibitors are, for example, trialkyl citrates, such as trimethyl citrate, tripropyl citrate, triisopropyl citrate, tributyl citrate, in particular triethyl citrate. Esterase inhibitors inhibit the enzyme activity and thereby reduce odor formation. It is possible to release free acid by cleavage of the citrate and lower the pH of the skin to the extent that the enzyme is inactivated by acylation. Further esterase inhibitors are sterol sulfates or phosphates, for example sulfates or phosphates of lanosterol, cholesterol, campesterol, stigmasterol and sitosterol, dicarboxylic acids and esters thereof, for example glutaric acid, monoethyl glutarate, diethyl glutarate, adipic acid, monoethyl adipate, diethyl adipate, malonic acid and diethyl malonate, hydroxycarboxylic acids and esters thereof, for example citric acid, malic acid, tartaric acid or diethyl tartrate and zinc glycinate.

In a preferred embodiment of the invention, the composition comprises at least one esterase inhibitor selected from the group consisting of trimethyl citrate, tripropyl citrate, triisopropyl citrate, tributyl citrate, triethyl citrate, lanosterol, cholesterol, campesterol, stigmasterol, sitosterol sulfate, sitosterol phosphate, glutaric acid, monoethyl glutarate, diethyl glutarate, adipic acid, monoethyl adipate, diethyl adipate, malonic acid, diethyl malonate, citric acid, malic acid, tartaric acid, diethyl tartrate and zinc glycinate.

The compositions according to the invention may comprise the esterase inhibitor in an amount of from 0.01 to 20, preferably from 0.1 to 10, more particularly from 0.5 to 5,% by weight, based on the solids content of the composition.

The term "antimicrobial agent" as used herein encompasses substances having bactericidal and/or bacteriostatic properties. These substances are generally active against gram-positive bacteria, such as 4-hydroxybenzoic acid and its salts and esters, N- (4-chlorophenyl) -N '- (3, 4-dichlorophenyl) -urea, 2,4,4' -trichloro-2 '-hydroxydiphenyl ether (triclosan), 4-chloro-3, 5-dimethylphenol, 2' -methylene-bis- (6-bromo-4-chlorophenol), 3-methyl-4- (1-methylethyl) -phenol, 2-benzyl-4-chlorophenol, 3- (4-chlorophenoxy) -propane-1, 2-diol, 3-iodo-2-propynyl butylcarbamate, chlorhexidine, 3,4,4' -Trichlorocarboxanilide (TTC), phenoxyethanol, glycerol monocaprate, glycerol monocaprylate, Glycerol Monolaurate (GML), Diglycerol Monocaprylate (DMC), N-alkylamides of salicylic acid, for example salicylic acid-N-octylamide or salicylic acid-N-decylamide.

In a preferred embodiment, the antibacterial agent is selected from the group consisting of chitosan, phenoxyethanol, 5-chloro-2- (2, 4-dichlorophenoxy) -phenol, 4-hydroxybenzoic acid and salts and esters thereof, N- (4-chlorophenyl) -N '- (3, 4-dichlorophenyl) -urea, 2,4,4' -trichloro-2 '-hydroxydiphenyl ether (triclosan), 4-chloro-3, 5-dimethylphenol, 2' -methylene-bis- (6-bromo-4-chlorophenol), 3-methyl-4- (1-methylethyl) -phenol, 2-benzyl-4-chlorophenol, 3- (4-chlorophenoxy) -propan-1, 2-diol, 3-iodo-2-propynyl butylcarbamate, chlorhexidine, 3,4,4' -trichlorocarbanilide (TTC), phenoxyethanol, glycerol monocaprate, glycerol monocaprylate, Glycerol Monolaurate (GML), Diglycerol Monocaprate (DMC), salicylic acid-N-alkylamide.

The composition according to the present invention may contain the antibacterial agent in an amount of 0.01 to 5% by weight, preferably 0.1 to 2% by weight, based on the solid content of the composition.

The 4,8,11-dodecatrienal according to the present invention can be preferably used for a surfactant-containing composition. Due to their characteristic fragrance properties and their persistence, tenaciousness and stability, they are particularly useful for providing odor, preferably fragrance impression, to surfactant-containing compositions, such as detergents, in particular laundry care products and all-purpose detergents. It may preferably be used to provide long lasting clean notes to surfactant containing compositions.

The composition according to the invention may therefore preferably comprise at least one surfactant. The surfactant may be selected from anionic, nonionic, cationic and/or amphoteric or zwitterionic surfactants. Surfactant-containing compositions, such as shower gels, bath foams, shampoos and the like, preferably contain at least one anionic surfactant.

The compositions according to the invention generally contain surfactants in amounts which add up to 0 to 40% by weight, preferably 0 to 20% by weight, more preferably 0.1 to 15% by weight, in particular 0.1 to 10% by weight, based on the total weight of the composition. Typical examples of nonionic surfactants are fatty alcohol polyglycol ethers, alkylphenol polyglycol ethers, fatty acid polyglycol esters, fatty acid amide polyglycol ethers, fatty amine polyglycol ethers, alkoxylated triglycerides, mixed ethers and mixed formals, optionally partially oxidized alkyl (alkenyl) oligoglycosides or glucuronic acid derivatives, fatty acid-N-alkylglucamides, protein hydrolysates (in particular wheat-based plant products), polyol fatty acid esters, sugar esters, sorbitan esters, polysorbates and amine oxides. If the nonionic surfactants contain polyglycol ether chains, they may have a conventional homologue distribution, although they preferably have a narrow homologue distribution.

The zwitterionic surfactant is a compound containing at least one quaternary ammonium group and at least one-COO group in the molecule^(-)or-SO₃ ^(-)A surface active compound of the group. Particularly suitable zwitterionic surfactants are the so-called betaines, such as N-alkyl-N, N-dimethylammonium glycinates, for example cocoalkyldimethylammonium glycinate, N-amidopropyl-N, N-dimethylammonium glycinates, for example cocoamidopropyl dimethylammonium glycinate, and 2-alkyl-3-carboxymethyl-3-hydroxyethylimidazolines containing 8 to 18 carbon atoms in the alkyl or acyl group, and cocoamidoethylhydroxyethyl carboxymethyl glycinate. Uses the CTFA name Cocamidopropyl Betaine as a humanThe known fatty acid amide derivatives are particularly preferred.

Amphoteric surfactants are also suitable, in particular as cosurfactants. The amphoteric surfactant is a surfactant which removes C in the molecule₈To C₁₈The alkyl or acyl radical containing, in addition to at least one free amino group and at least one-COOH-or-SO group₃H-groups and capable of forming internal salts. Examples of suitable amphoteric surfactants are N-alkylglycines, N-alkylpropionic acids, N-alkylaminobutyric acids, N-alkyliminodipropionic acids, N-hydroxyethyl-N-alkylamidopropylglycines, N-alkyltaurines, N-alkylsarcosines, 2-alkylaminopropionic acids and alkylaminoacetic acids having from about 8 to 18 carbon atoms in the alkyl radical. Particularly preferred amphoteric surfactants are N-cocoalkylamidopropionate, cocoamidoethyl aminopropionate, and acylsarcosine.

Anionic surfactants are characterized by water-soluble anionic groups (such as carboxylate, sulfate, sulfonate, or phosphate) and lipophilic groups. Skin-safe anionic surfactants are well known and commercially available to practitioners from relevant textbooks. They are, in particular, alkyl sulfates (in the form of their alkali metal, ammonium or alkanolammonium salts), alkyl ether sulfates, alkyl ether carboxylates, acyl isethionates, acyl sarcosinates, linear C-containing salts₁₂-C₁₈Alkyl or acyl taurines, as well as sulfosuccinates and acyl glutamates (in the form of their alkali metal or ammonium salts).

Particularly suitable cationic surfactants are quaternary ammonium compounds, preferably ammonium halides, more particularly ammonium chlorides and bromides, such as alkyltrimethylammonium chlorides, dialkyldimethylammonium chlorides and trialkylmethylammonium chlorides, for example cetyltrimethylammonium chloride, stearyltrimethylammonium chloride, distearyldimethylammonium chloride, lauryldimethylammonium chloride, lauryldimethylbenzylammonium chloride and tricetylmethylammonium chloride. In addition, readily biodegradable quaternary ammonium ester compounds, such as the dialkyl ammonium methosulphates and methyl hydroxyalkyl dialkoxy radicals sold under the name StepandexecAlkyl ammonium methosulfate, andthe corresponding products of the series can be used as cationic surfactants. "Esterquats" are generally understood to be quaternized fatty acid triethanolamine ester salts. They may provide a particularly soft feel to the composition. They are known substances which are prepared by processes related to organic chemistry. Further cationic surfactants suitable for use according to the invention are quaternized protein hydrolysates.

One embodiment of the present invention relates to a composition comprising 4,8,11-dodecatrienal and at least one additional component selected from the group consisting of aromatic chemicals, surfactants, oil components, antioxidants, deodorizing actives, and solvents, wherein the composition does not comprise 1,5, 9-cyclododecatriene.

In this embodiment of the invention, the additional components are preferably those described above and are suitably used in the amounts described above.

The composition according to the present invention may be selected from, but is not limited to, perfume compositions, body care compositions (including cosmetic compositions and oral dental hygiene products), hygiene articles, cleaning compositions (including dishwashing compositions), textile detergent compositions, compositions for dispensers, food products, food supplements, pharmaceutical compositions and crop protection compositions.

The composition is preferably a fragrance chemical composition, more preferably a perfume composition.

Suitable compositions are, for example, perfume compositions, body care compositions (including cosmetic compositions and oral dental hygiene products), hygiene articles, cleaning compositions (including dishwashing compositions), textile detergent compositions, compositions for dispensers, food products, food supplements, pharmaceutical compositions and crop protection compositions.

The perfume composition may be selected from fine fragrance products (fine fragrances), air fresheners in liquid form, gel form or applied to a solid carrier, aerosol sprays, perfumed detergents, fragranced candles and oils, such as lamp or massage oils.

Examples of fine fragrance products (fine fragrances) are essence extracts, Eau de Parfums, Eau de Toilettes, Eau de colonnes, Eau de Solide and extract Parfum.

Body care compositions include cosmetic compositions and oral dental hygiene products and may be selected from after-shave products, before-shave products, splash-on-water (splash gels), solid and liquid soaps, shower gels, shampoos, shaving soaps, shaving foams, bath oils, oil-in-water, water-in-oil and water-in-oil cosmetic emulsions, such as skin creams and water (ons), face creams and water (ons), sun creams and water (ons), after-sun creams and water (ons), hand creams and water (ons), foot creams and water (ons), depilatories and water (ons), after-shave creams and water (ons), make-up creams and water (ons), hair care products, such as hair sprays, hair gels, hair styling water (setting hair lotions), hair conditioners, shampoos, permanent and semi-permanent hair colorants, hair styling compositions such as cold wave and hair softening compositions, Hair tonics, hair creams and hair lotions, deodorants and antiperspirants, such as underarm sprays, roll-ons, deodorant sticks and creams, decorative cosmetics, such as eyeliners, eyeshadows, nail varnishes, color cosmetics, lipsticks and mascaras, and oral dental hygiene products, such as toothpaste, dental floss, mouthwashes, breath fresheners, dental foams, dental gels and dental strips.

The hygiene article may be selected from sticks, insecticides, insect repellents, propellants, rust removers, perfumed refreshing wipes, armpit pads, baby diapers, sanitary napkins, toilet paper, cosmetic pads, handkerchiefs, dishwashing agents and deodorants;

cleaning compositions, such as solid surface cleaners, may be selected from perfumed acidic, alkaline and neutral cleaners, such as floor cleaners, window cleaners, dishwashing compositions for hand and machine washing, bathroom and sanitary cleaners, scouring milks (scouring milks), solid and liquid toilet cleaners, powder and foam carpet cleaners, waxes and polishes, such as furniture polishes, floor polishes, shoe polishes, disinfectants, surface disinfectants and sanitary cleaners, brake disc cleaners, pipe cleaners, scale removers, grill and oven cleaners, algae and moss removers, mold removers, facade cleaners.

The textile detergent composition may be selected from the group consisting of liquid detergents, powder detergents, laundry pretreaters such as bleaches, soaking and cleaning agents, fabric softeners, washing soaps, washing tablets.

Food products are understood to mean raw, cooked or processed edible substances, ice, beverages or ingredients for or intended for full or partial human consumption, or chewing gums, fudge, jelly and confectionery.

Food supplements are edible products containing dietary ingredients intended to further increase the nutritional value of the diet. The dietary component may be one or any combination of the following: vitamins, minerals, herbs or other substances, amino acids, dietary substances used by humans to supplement the diet by increasing total dietary intake, concentrates, metabolites, ingredients or extracts. Food supplements may be in many forms, such as tablets, capsules, gelcaps, caplets (gelcaps), liquids, or powders.

Pharmaceutical compositions include compositions intended for use in the diagnosis, cure, mitigation, treatment or prevention of disease, as well as articles of manufacture (non-food) intended to affect the structure or any function of the human or other animal body.

Crop protection compositions include compositions intended for the management of plant diseases, weeds and other pests (vertebrates and invertebrates) that destroy crops and forestry.

The composition according to the invention may further comprise one or more substances, such as: preservatives, abrasives, anti-acne agents, anti-skin ageing agents, anti-cellulite agents, anti-dandruff agents, anti-inflammatory agents, anti-irritants, irritation-reducing agents, astringents, antiperspirant agents, preservatives, antistatic agents, binders, buffers, carrier materials, chelating agents, cell stimulants, conditioning agents, depilatory agents, emulsifiers, enzymes, essential oils, fibers, film-forming agents, fixatives, foam-forming agents, foam stabilizers, anti-foaming agents, foam boosters, fungicides, gelling agents, gel-forming agents, hair care agents, hair setting agents, hair softeners, moisturizers, moisturizing substances, bleaching agents, enhancers, stain removers, optical brighteners, saturants, stain removers, friction reducing agents, lubricants, moisturizers, ointments, opacifiers, plasticizers, covering agents, polishing agents, shine agents (shine agents), Polymers, powders, proteins, fat liquoring agents (refatting agents), exfoliants, silicones, skin sedatives, skin cleansers, skin care agents, skin healing agents, skin whitening agents, skin protectants, skin softeners, cooling agents, skin cooling agents (skin-cooling agents), warming agents (warming agents), skin warming agents (skin-warming agents), stabilizers, UV absorbers, UV filters, fabric softeners, suspending agents, skin tanning agents, thickeners, vitamins, waxes, fats, phospholipids, saturated fatty acids, mono-or polyunsaturated fatty acids, alpha-hydroxy acids, polyhydroxy fatty acids, liquefying agents, dyes, color protectants, pigments, anti-corrosion agents, polyols, electrolytes, or silicone derivatives.

In a preferred embodiment, the composition according to the invention comprises 4,8, 11-dodecatrienol comprising less than 0.2% by weight of 1,5,9-cyclododecatriene, based on the weight of 4,8, 11-dodecatrienol. In a preferred embodiment of the invention, the composition comprises 4,8, 11-dodecatrienol comprising less than 0.1 wt%, preferably less than 0.05 wt%, of 1,5,9-cyclododecatriene, based on the weight of 4,8, 11-dodecatrienol. One embodiment of the present invention relates to compositions comprising 4,8,11-dodecatrienal and no 1,5, 9-cyclododecatriene.

The following examples serve to further illustrate the invention.

Examples

Preparation of 4,8, 11-dodecatrienol

Examples 1 and 2 of WO 2010/086313 were repeated and a mixture comprising 77% by weight of 4,8, 11-dodecatrienol, 8.7% by weight of cyclododecadienone, 13.9% by weight of 1,5,9-cyclododecatriene and 0.4% by weight of unidentified compound was obtained. This mixture was rectified in a batch distillation column (diameter 43mm, packed with 135.5cm Montz A3-1000 packings) under reduced pressure as follows:

the distillation was carried out at a constant head pressure of 5 mbar and the pressure difference between the top and the bottom of the column was about 4-5 mbar. During start-up, the column was run at full reflux and the reflux ratio was then adjusted to 5: 1. Under these conditions, 4,8,11-dodecatrienal having a purity of 98.2% by weight was obtained. The amount of 1,5,9-cyclododecatriene was determined by gas chromatography using a Stabilwax column (column length 90m, internal diameter 0,32mm, membrane thickness 0.5 μm; commercially available from Restek) using the following temperature program: isothermal at 80 deg.C, 8 deg.C/min to 160 deg.C, 16min, 4 deg.C/min to 260 deg.C, 15 min; helium gas, flow 1,4 ml/min. The amount of 1,5,9-cyclododecatriene is less than 0.05% by weight, based on the weight of 4,8, 11-dodecatrienal. The 4,8,11-dodecatrienal thus obtained had a weight ratio of (E, Z) -4,8, 11-dodecatrienal to (Z, E) -4,8, 11-dodecatrienal of 1: 1.1.

2. Performance testing

To evaluate the properties, a 1.0% by weight solution of 4,8, 11-dodecatrienol obtained according to example 1 above in triethyl citrate was prepared (═ solution a).

2a) Olfactory assessment

The absorbent paper was immersed in solution a and immediately thereafter evaluated by a panel of 4 trained perfumers at 20 ℃. Olfactory notes are graded from 1 (very weak) to 6 (strong).

Smell fragrant tune	Clean and clean	Ozone generator	Oceans	Citrus fruit	Cyclamen comes
						Example 1	5	4	4	3	3

2b) Olfactory assessment-Long term

The absorbent paper prepared according to example 2a was stored at 20 ℃ and ambient humidity and the olfactory impression was reevaluated by the panel of 4 trained perfumers after 1 day, 5 days, 7 days, 14 days and 28 days. Over the total time span and even after 28 days, the olfactory impression is still clearly perceptible and its properties do not change.

2c) Staying power on textiles (persistence)

0.2 grams of solution a was included in the textile detergent composition:

textile detergent composition a:

component [ CAS No ]]	wt.-％
		MEA-C10-13 alkylbenzenesulfonate [85480-55-3 ]]	12.4
MEA-COCOATE[66071-80-5]	7.5
		C14-15PARETH-7[68951-67-7]	5.7
Ethanol [64-17-5 ]]	2
		Solution A	0.2
Water (W)	Is supplemented to 100

The test cloths made of cotton were washed in a domestic washing machine at 40 ℃. Olfactory evaluations were performed directly on the wet laundry after washing and at various time points after washing. Furthermore, on dry cloths, olfactory assessments were still performed at different time points. Olfactory properties were graded by a panel of 4 trained perfumers, scoring 0 (no odor) to 10 (very strong odor). The following table summarizes the olfactory evaluation results of cotton after the wash cycle with textile detergent composition a:

2d) stability in compositions

The stability of the compositions comprising 4,8,11-dodecatrienal under different storage conditions was evaluated. The following compositions were prepared:

shampoo composition:

the olfactory properties of this shampoo composition as well as textile detergent composition a (as described in 2C above) and fine fragrance composition 1A (as described in 3 below) were evaluated directly after preparation and after 3 months of storage at the storage conditions described in table C. Olfactory properties were graded by a panel of 4 trained perfumers, scoring 0 (no odor) to 10 (very strong odor).

Table C:

3. advantageous perfume composition

Solution a as described above was formulated in compositions according to tables 2 and 3. The amounts given in tables 2 and 3 are weights in grams.

TABLE 2 perfume compositions 1A and 1B

TABLE 3 fragrance compositions 2A and 2B