Composition for improving odor
阅读说明：本技术 用于改善气味的组合物 (Composition for improving odor ) 是由 N·舒尔策 C·施密特 于 2017-05-05 设计创作，主要内容包括：本发明涉及一种制剂,含有：(i)一种物质混合物,其含有(a)一种、两种或更多种化合物,其选自组包括(a1)式(I)的醇单萜,其中R1是H或甲基,R2是H或C2-烯基,并且R3是含有4至10碳原子的直链或支化、饱和或不饱和烃基,及其对映异构体、非对映异构体、外消旋体、溶剂化物及其生理相容性盐,和/或(a2)双环环氧单萜,(b)至少两种式(II)的内酯,其中R4是H或甲基,R5是含有2至10碳原子的直链或支化、饱和或不饱和烃基,并且n是1或2,及其对映异构体,非对映异构体和外消旋体,(c)一种、两种或多种溶剂,选自组包括乙醇、水、二丙二醇(DPG)、邻苯二甲酸二乙酯(DEP)、丙二醇(PG)、肉豆蔻酸异丙酯(IPM)、棕榈酸异丙酯(IPP)、柠檬酸三乙酯(TEC)、三醋精(TRI)、1,2-丙二醇、1,3-丙二醇、丙硫醇、戊二醇、己二醇、辛二醇、癸二醇<Image he="50" wi="346" file="DDA0002257015810000011.GIF" imgContent="drawing" imgFormat="GIF" orientation="portrait" inline="no"></Image>十二烷醇、4-羟基苯乙酮<Image he="48" wi="310" file="DDA0002257015810000012.GIF" imgContent="drawing" imgFormat="GIF" orientation="portrait" inline="no"></Image>甘油、丁二醇、戊二醇、己二醇、癸二醇、碳酸丙烯酯、碳酸丁烯酯、碳酸甘油酯、2-苄基庚醇、月桂醇、异丁酸三甲基羟基戊酯、辛酸甘油酯、乙基己基甘油、苯甲酸苄酯(BB),以及任选地(d)其他香料物质或香精,选自组包括3-苯基丁醛(草青醛)、乙酰甲基甲醇、茴香脑、乙酸茴香酯、二氢丁香酚、甲酸芳樟酯、2-甲基癸醛、2-苄基-2-甲基丁-3-烯腈<Image he="46" wi="386" file="DDA0002257015810000013.GIF" imgContent="drawing" imgFormat="GIF" orientation="portrait" inline="no"></Image>乙酸3-己烯酯、乙酸苏合香酯、belanis、香茅醛、乙酸肉桂酯、rhubafuran、β-紫罗兰酮、anther、乙酸异戊二烯酯、2-苯丙醛、4-(4-羟苯基)丁-2-酮<Image he="49" wi="311" file="DDA0002257015810000014.GIF" imgContent="drawing" imgFormat="GIF" orientation="portrait" inline="no"></Image>苯氧基乙酸乙酯、异甲基紫罗兰酮、γ-萜品烯、柠檬烯、新环柠檬醛、甲基薰衣草酮、丙酸苏合香酯、丙酸苯乙酯、柠檬醛、4-异戊基环己醇<Image he="48" wi="264" file="DDA0002257015810000015.GIF" imgContent="drawing" imgFormat="GIF" orientation="portrait" inline="no"></Image>4-甲基-2-苯基-3,6-二氢-2H-吡喃/4-亚甲基-2-苯基四氢吡喃(Rosyrane super)、羟基柠檬腈、苯乐戊醇、苯乙酸异戊酯、大马酮、silvial、桃酮、降龙涎醚、乙酰吡嗪、三甲基吡嗪、乙酸异戊酯、对甲酚甲基醚、榛子酮、乙酸环己酯、胡椒醛、苯乙酮、茴香醛、对甲基苯乙酮、藜芦醛、茴香酸甲酯和vertoprenal；(ii)式(III)的醛类,其中R6是饱和或不饱和的直链羟基,和/或(iii)式(IV)的自由脂肪酸,其中R7是直链或支化的饱和烃基。<Image he="261" wi="700" file="DDA0002257015810000016.GIF" imgContent="drawing" imgFormat="GIF" orientation="portrait" inline="no"></Image>(The invention relates to a preparation, comprising: (i) a mixture of substances containing (a) one, two or more compounds selected from the group comprising (a1) an alcoholic monoterpene of formula (I) wherein R1 is H or methyl, R2 is H or C2-alkenyl, and R3 is a straight-chain or branched, saturated or unsaturated hydrocarbyl radical containing 4 to 10 carbon atoms, and enantiomers, diastereomers, racemates, solvates and physiologically compatible salts thereof, and/or (a2) a bicyclic epoxy monoterpene, (b) at least two lactones of formula (II) wherein R4 is H or methyl, R5 is a straight-chain or branched, saturated or unsaturated hydrocarbyl radical containing 2 to 10 carbon atoms, and n is 1 or 2, and enantiomers, diastereomers and racemates thereof, (C) one, two or more solvents selected from the group comprising ethanol, water, dipropylene glycol (DPG), diethyl phthalate (DEP), Propylene Glycol (PG), isopropyl myristate (IPM), isopropyl palmitate (IPP), triethyl citrate (TEC), Triacetin (TRI), 1, 2-propanediol, 1, 3-propanediol, propanethiol, pentanediol, hexanediol, octanediol, decanediol Dodecanol, 4-hydroxyacetophenone Glycerol, butanediol, pentanediol, hexanediol, decanediol, propylene carbonate, butylene carbonate, glycerol carbonate, 2-benzylheptanol, lauryl alcohol, trimethylhydroxypentyl isobutyrate, glycerol octanoate, ethylhexylglycerol, Benzyl Benzoate (BB), and optionally (d) other perfume substances or essences selected from the group consisting of 3-phenylbutanal (oxalaldehyde),Acetylmethyl methanol, anethole acetate, dihydroeugenol, linalyl formate, 2-methyldecanal, 2-benzyl-2-methylbut-3-enenitrile 3-hexenyl acetate, styryl acetate, balanis, citronellal, cinnamyl acetate, rhubafuranan, β -ionone, anther, prenyl acetate, 2-phenylpropionaldehyde, 4- (4-hydroxyphenyl) butan-2-one Ethyl phenoxyacetate, iso-methyl ionone, gamma-terpinene, limonene, neocyclocitral, methyl lavandulone, styryl propionate, phenylethyl propionate, citral, 4-isoamylcyclohexanol 4-methyl-2-phenyl-3, 6-dihydro-2H-pyran/4-methylene-2-phenyltetrahydropyran (rosylane super), hydroxycitriles, mellopentanol, isoamyl phenylacetate, damascenone, silvalial, peach ketone, ambrox, acetylpyrazine, trimethylpyrazine, isoamyl acetate, p-cresol methyl ether, hazelnut ketone, cyclohexyl acetate, piperonal, acetophenone, anisaldehyde, p-methylacetophenone, veratraldehyde, methyl anisate, and verteprenal; (ii) (ii) aldehydes of the formula (III) in which R6 is a linear, saturated or unsaturated hydroxyl group, and/or (III) free fatty acids of the formula (IV) in which R7 is a linear or branched, saturated hydrocarbon group.)
1. Preparation of containing
(i) A mixture of substances comprising
(a) One, two or more compounds selected from the group consisting of
(a1) An alcohol monoterpene of formula (I)
Wherein
R1 is H or methyl, R2 is H or C2-alkenyl and R3 is a straight-chain or branched, saturated or unsaturated hydrocarbon radical containing from 4 to 10 carbon atoms, and the enantiomers, diastereomers, racemates, solvates and physiologically compatible salts thereof,
and/or
(a2) The bicyclic epoxy monoterpene is a compound of the formula,
(b) at least two lactones of the formula (II)
Wherein
R4 is H or methyl, R5 is a straight-chain or branched, saturated or unsaturated hydrocarbon radical containing from 2 to 10 carbon atoms, and n is 1 or 2, and enantiomers, diastereomers and racemates thereof, and
(c) one, two or more solvents selected from the group consisting of ethanol, water, dipropylene glycol (DPG), diethyl phthalate (DEP), Propylene Glycol (PG), isopropyl myristate (IPM), isopropyl palmitate (I)PP), triethyl citrate (TEC), Triacetin (TRI), 1, 2-propanediol, 1, 3-propanediol, propanethiol, pentanediol, hexanediol, octanediol, decanediol
and optionally
(d) Other perfume materials or essences selected from the group consisting of 3-phenylbutanal (oxalaldehyde), acetylmethylmethanol, anethole acetate, dihydroeugenol, linalyl formate, 2-methyldecanal, 2-benzyl-2-methylbut-3-enenitrile(s) ((s))
and
(ii) aldehydes of the formula (III)
Wherein R6 is a saturated or unsaturated linear hydroxyl group,
and/or
(iii) Free fatty acids of formula (IV)
Wherein R7 is a straight or branched saturated hydrocarbon group.
2. A mixture of substances comprising
(a) One, two or more compounds selected from the group consisting of
(a1) An alcohol monoterpene of formula (I)
Wherein
R1 is H or methyl, R2 is H or C2-alkenyl and R3 is a straight-chain or branched, saturated or unsaturated hydrocarbon radical containing from 4 to 10 carbon atoms, and the enantiomers, diastereomers, racemates, solvates and physiologically compatible salts thereof,
and/or
(a2) Bicyclic epoxy monoterpenes
(b) At least two lactones of the formula (II)
Wherein
R4 is H or methyl, R5 is a straight-chain or branched, saturated or unsaturated hydrocarbon radical containing from 2 to 10 carbon atoms and n is 1 or 2, and enantiomers, diastereomers and racemates thereof,
(c) one, two or more solvents selected from the group consisting of
(c1) Ethanol and/or
(c2) One, two or more solvents selected from the group consisting of water, dipropylene glycol (DPG), diethyl phthalate (DEP), Propylene Glycol (PG), isopropyl myristate (IPM), isopropyl palmitate (IPP), triethyl citrate (TEC), Triacetin (TRI), 1, 2-propanediol, 1, 3-propanediol, propanethiol, pentanediol, hexanediol, octanediol, decanediolDodecanol, 4-hydroxyacetophenone (A), (B), (C
and optionally
(d) Other flavor materials or essences selected from the group consisting of 3-phenylbutanal (oxalaldehyde), acetylmethylmethanol, anethole acetate, dihydroeugenol, aryl formate, 2-methyldecanal, 2-benzyl-2-methylbut-3-enenitrile (A), (B), (C
3. The substance mixture according to claim 2, wherein ingredient (a1) is selected from the group consisting of linalool, geraniol, freesiol and nerolidol.
4. Mixture of matter according to at least one of claims 2 and/or 3, wherein component (a2) is selected from the group comprising 1, 4-cineole and 1, 8-cineole.
5. The mixture of substances according to at least one of claims 2 to 4, wherein component (b) is selected from the group consisting of lactones of (II) and enantiomers, diastereomers and racemates thereof.
Wherein R4 is H, R5 is a straight chain saturated hydrocarbon group containing 2 to 8 carbon atoms, and n is 1 or 2.
6. The substance mixture according to at least one of claims 2 to 5, wherein component (c) is ethanol (component c1) and/or one, two or more selected from the group consisting of dipropylene glycol (DPG), diethyl phthalate (DEP), Propylene Glycol (PG), isopropyl myristate (IPM), isopropyl palmitate (IPP), triethyl citrate (TEC), Triacetin (TRI), 1, 2-propanediol, 1, 3-propanediol, propanethiol, pentanediol, hexanediol, octanediol, decanediol
7. The substance mixture according to at least one of claims 2 to 6, wherein component (d) is selected from the group consisting of 3-phenylbutanal (oxalaldehyde), acetylmethylmethanol, 2-methyldecanal, 2-benzyl-2-methylbut-3-enenitrile (C:) (C: (C))
8. Substance mixture according to at least one of claims 2 to 7, characterized in that it contains
(i)0.0000001 to 80% by weight of component (a),
(ii)0.0000001 to 80% by weight of component (b),
(iii)0.0000001 to 98% by weight of component (c),
(iv)0 to 80% by weight of component (d),
with the proviso that the quantitative data for the other optional constituents add up to 100% by weight, based on the total amount of the substance mixture.
9. The substance mixture according to at least one of claims 2 to 8, characterized in that component (c1) has an ethanol content of less than 30% by weight, based on the total amount of the substance mixture.
10. A process for preparing a substance mixture according to at least one of claims 2 to 9, comprising the steps of:
i) mixing (a), (b), (c) and optionally (d), wherein components (a) to (d) are present in the form of solids, solutions, extracts, aqueous extracts and enriched preparations or concentrates,
and optionally
ii) spray drying the substance mixture thus obtained.
11. A flavour or fragrance composition comprising a mixture of substances according to at least one of claims 2 to 9 or a formulation according to claim 1 in combination with an additional flavour or fragrance substance, wherein the fragrance composition is in liquid or solid form.
12. Use of a substance mixture according to at least one of claims 2 to 9 or a flavour or fragrance composition according to claim 11 to reduce and/or mask unwanted off-flavours in oleochemical formulations.
13. Use according to claim 12, wherein the undesirable off-notes in oleochemical preparations are derived from aldehydes of formula (III)
Wherein R6 is a saturated or unsaturated, linear hydrocarbon group,
and/or free fatty acids of formula (IV)
Wherein R7 is straight or branched chain, including hydrocarbyl,
use of the resulting undesirable off-flavour.
14. Use of the formulation according to claim 1 or of the substance mixture according to at least one of claims 2 to 9 or of the fragrance or fragrance composition according to claim 11 as a fragrance or perfume.
15. End product containing a formulation according to claim 1 or a mixture of substances according to at least one of claims 2 to 9 or a perfume or fragrance composition according to claim 11, wherein the end product is selected from the group consisting of perfumes, detergents, washing powders, air fresheners, candles, dishwashing liquids, fabric softeners, skin creams, lip products, make-up removers, hair conditioners, lotions, shampoos, body washes and soaps and solid and liquid embodiments thereof.
Technical Field
The present invention is in the field of oleochemical products and relates to mixtures of substances that reduce or prevent the sensory perception of substances that form and produce undesirable off-flavors in oleochemical preparations, as well as methods of making and uses of the mixtures of substances.
Prior Art
Oleochemical products and formulations in the fields of cosmetics, household products, oral care products and fine perfumery contain fats, fatty acids, fatty acid esters, fatty acid salts or ingredients based on fats or fatty acids. The commonality of all these materials is that they have a typical fatty odour which further generates other unpleasant odours after relatively long storage. The reason for this is not only the short-chain free fatty acids released in the saponification of triglycerides, but also in particular the aldehydes and other substances produced during oxidation.
These unwanted off-flavours have a negative impact on the odour or flavour and quality of the product or formulation. Conventional odorants or perfumes/fragrances mask the off-taste only to a limited extent and, if necessary, the use concentration must be increased, which in turn leads to increased costs.
One way of solving this problem is to subject the batches, which are objectionable in terms of odor, to a post-treatment, so-called deodorization. This involves treating the raw material with hot water vapour, the odour carrier being largely evaporated. However, this method requires a large amount of input energy. This method is naturally not predictable from an economic point of view, particularly when it comes to the treatment of fats and oils, which are as cheap as possible and which essentially account for the highest proportion of the undesired odour carriers.
In some cases, unpleasant odours may be encapsulated by the addition of an encapsulating agent, as described in WO 2009131748 a 1. However, this method is also difficult to implement from an economic point of view. In the case of this method, the addition of a flavoured or fragrant substance or aromatizer may also be bound by the coating agent, thereby adversely affecting the desired flavour or taste.
To date, the most common alternative is to add fragrances to the odour-wise objectionable raw materials-or to the end products prepared therefrom-which mask the unpleasant odours or tastes or combine them to form new odours or tastes of reduced discomfort. This method is likewise complicated and expensive, since a large amount of such masking substances is necessary up to now.
Document EP 2865739A 1 discloses mixtures containing lactones of the formula (Ia) or (Ib)
Wherein R1 is a linear or branched, saturated or unsaturated, optionally hydroxy-substituted hydroxy group containing 2 to 22 carbon atoms and 0 or 1 to 3 double bonds, and n is 1 or 2, for use in oleochemical formulations to mask off-flavours.
Document WO 03/070871 a1 relates to a composition for counteracting and/or masking the odor generated during soaking and/or hand washing of laundry detergent. Disclosed are compositions containing one or more odor-inhibiting substances selected from the group consisting of compounds of formula (I), C-11 aldehyde (undecanal), C-11 lactam, C-12 laurate aldehyde, ethyl rhodizonate, galbanum (galbanum) oil, ligustral (hiveral), p-methyl cresol, methyl acetophenone, patchouli oil, decenol (decenol), undecenal, allylcyclohexyl propionate, musk lactone (musk lactone), amyl salicylate, damascone, dihydromyrcenol, ethyl vanillin, florazone, irisonitrile (irisonitrile), gamma-methyl ionone, gamma-nonalactone, paracetamol (pandanol), rose oxide L, and tridecene-2-carbonitrile.
Compounds of formula (I) according to WO 03/070871A 1
Document US 2006/0207037 a1 discloses a perfume or perfume mixture for masking odors caused by nitrogen-containing substances, such as ammonia and substituted amines, but also other kinds of odors, such as sweat odors, body odors, bathroom odors, kitchen odors, etc. Further, perfume mixtures are disclosed which are gamma undecalactones, combinations of gamma decalactone and diethyl phthalate (DEP) and combinations of gamma undecalactones, geraniol, linalool and diethyl phthalate (DEP). The primary use of these perfume mixtures is hair dyes, but can also be used in products ranging from household cleaners to cosmetics, including antiperspirants, deodorants, sunless lotions, shampoos, conditioners, hand washes, body lotions, and permanent wave agents.
Document WO 2004/009750 a1 describes perfume ingredients, mixtures thereof and perfume compositions for reducing or preventing body odour. The identified perfume ingredients prevent the production of malodorous steroids, which are produced by microorganisms present on the skin surface. The compositions are described as anti-odor actives and deodorant actives for use in cosmetics or perfumes, antiperspirants and deodorants. Combinations of gamma-octalactone, gamma-nonalactone, geraniol, dihydrolinalool, and tetrahydrogeraniol are disclosed.
Document WO 96/04940 relates to an aqueous composition for reducing unpleasant odor or odor perception comprising a) from about 0.01% to about 1% of a perfume, based on the weight of the composition; b) optionally, but preferably, from about 0.1% to about 5% of a water-soluble cyclodextrin, based on the weight of the composition; c) optionally, but preferably, from about 0.1% to about 10% of a water-soluble metal salt, based on the weight of the composition; d) optionally, but preferably, from about 0% to about 3% of a solubilizing agent, based on the weight of the composition; and e) an aqueous carrier. Ingredient a) may contain various fragrances, such as gamma-decalactone and gamma-dodecalactone. The composition is preferably sprayed onto textiles, especially garments, without the need for cleaning or dry cleaning.
Despite the above alternatives known from the prior art, there is still a continuing strong need in the field of oleochemical products for new substance mixtures which overcome the above-mentioned drawbacks and which enable the production of high quality products and formulations free from unwanted odours or off-flavours.
Further, the unwanted off-flavours also have an impact on the use of products and formulations, as the perfuming or aromatizing agents commonly found in washing, spraying or painting processes are ineffective, and the unwanted off-flavours are particularly pronounced.
It is therefore an object of the present invention to provide new, highly active substance mixtures which are capable of counteracting, reducing or masking unpleasant odours or off-flavours present in oleochemical raw materials and in end-products prepared therefrom, preferably perceived by the consumer as pungent, oxidising, choking, rancid, fatty, animal, caprine, fermented, mouldy, herbaceous and nauseous odours, even at very low concentrations.
It is therefore a second object of the present invention to provide a new, highly active mixture of substances capable of counteracting, reducing or masking the above mentioned unwanted off-flavours during use and after elution of oleochemicals or end-products, in particular from the skin surface, said mixture of substances containing said highly active mixture of substances.
Disclosure of Invention
The invention provides, in a first aspect, a formulation comprising
(i) A mixture of substances comprising
(a) One, two or more compounds selected from the group consisting of
(a1) An alcohol monoterpene of formula (I)
Wherein
R1 is H or methyl, R2 is H or C2-alkenyl and R3 is a straight-chain or branched, saturated or unsaturated hydrocarbon radical containing from 4 to 10 carbon atoms, and the enantiomers, diastereomers, racemates, solvates and physiologically compatible salts thereof,
and/or
(a2) The bicyclic epoxy monoterpene is a compound of the formula,
(b) at least two lactones of the formula (II)
Wherein
R4 is H or methyl, R5 is a straight-chain or branched, saturated or unsaturated hydrocarbon radical containing from 2 to 10 carbon atoms and n is 1 or 2, and enantiomers, diastereomers and racemates thereof,
(c) one, two or more solvents selected from the group consisting of ethanol, water, dipropylene glycol (DPG), diethyl phthalate (DEP), Propylene Glycol (PG), myristic acidIsopropyl ester (IPM), isopropyl palmitate (IPP), triethyl citrate (TEC), Triacetin (TRI), 1, 2-propanediol, 1, 3-propanediol, propanethiol, pentanediol, hexanediol, octanediol, decanediol
and optionally
(d) Other perfume materials or essences selected from the group consisting of 3-phenylbutanal (oxalaldehyde), acetylmethylmethanol, anethole acetate, dihydroeugenol, linalyl formate, 2-methyldecanal, 2-benzyl-2-methylbut-3-enenitrile(s) ((s))
and
(ii) aldehydes of the formula (III)
Wherein R6 is a saturated or unsaturated linear hydroxyl group,
and/or
(iii) Free fatty acids of formula (IV)
Wherein R7 is a straight or branched saturated hydrocarbon group.
In a preferred embodiment, the formulation according to the invention is an oleochemical formulation.
In a preferred embodiment, the preparations according to the invention contain at least two, three or four substances of group (a).
In another preferred embodiment, ingredient (a1) is selected from the group consisting of linalool, geraniol, freesiol and nerolidol and enantiomers, diastereomers, racemates, solvates and physiologically compatible salts thereof,
in another preferred embodiment, the bicyclic epoxy monoterpene (ingredient (a2)) is an epoxy p-menthane derivative, and the compounds 1, 4-cineole and 1, 8-cineole are particularly preferred.
In a preferred embodiment, the formulations according to the invention contain at least two-optionally three or four-lactones, selected from the group comprising lactones of formula (II) and enantiomers, diastereomers and racemates thereof, wherein R4 is H, R5 is a linear saturated hydrocarbon radical containing from 2 to 10 carbon sources, and n is 1 or 2, particularly preferably wherein R4 ═ H and R5 ═ linear saturated hydrocarbon radicals containing from 2 to 8 carbon atoms and n ═ 1 or 2.
In another preferred embodiment, the formulations according to the invention contain at least two, optionally three or four, lactones selected from the group consisting of γ -dodecalactone, γ -decalactone, γ -undecalactone, δ -decalactone, δ -dodecalactone, 4-methyl- γ -nonalactone, 3-methyl- γ -decalactone, γ -nonalactone, δ -nonalactone, γ -octalactone, δ -octalactone, γ -heptalactone, δ -heptalactone, γ -caprolactone and δ -caprolactone, preferably γ -dodecalactone, γ -decalactone, δ -decalactone and δ -dodecalactone.
In a preferred embodiment, the aldehydes of the formula (III) are selected from the group consisting of hexanal, heptanal, octanal, nonanal, decanal, hexenal, heptenal, octenes, nonenal, decenal, undecenal, dodecenal, adienal, heptadienal, octadienal, nonadienal, decadienal, undecenal, dodecadienal, octenal, nontrienoal, decatrienal, undecenal, dodecatrienol, hexanal, octanal, nonanal, hexenal, heptenal, octenal, heptadienal, octadienal, decadienal and decatrienol.
In another preferred embodiment, the free fatty acids of formula (IV) are selected from the group comprising butyric, valeric, isovaleric, caproic, enanthic, caprylic, pelargonic, capric, undecanoic and dodecanoic acids, with caproic, caprylic and capric acids being particularly preferred.
In a further preferred embodiment, the aldehydes of the formula (III) are selected from the group consisting of hexanal, heptanal, octanoic acid, nonanal, decanal, hexenal, heptenal, octenal, nonenal, decenal, undecenal, dodecenal, adienal, heptadienal, octadienal, nonadienal, decadienal, undecenal, dodecadienal, octenal, nontrienoal, decatrienol, undecenal, dodecatrienol, particularly preferably hexanal, octanal, nonanal, hexenal, heptenal, octenal, heptadienal, octadienal, decadienal and decatrienol,
and
the free fatty acids of formula (IV) are selected from the group comprising butyric, valeric, isovaleric, caproic, enanthic, caprylic, pelargonic, capric, undecanoic and dodecanoic acids, caproic, caprylic and capric acids being particularly preferred.
In a preferred embodiment, component (c) of the formulation according to the invention is one, two, or more solvents selected from the group comprising ethanol, water, dipropylene glycol (DPG), diethyl phthalate (DEP), Propylene Glycol (PG), isopropyl myristate (IPM), isopropyl palmitate (IPP), triethyl citrate (TEC), Triacetin (TRI), 1, 2-propanediol, 1, 3-propanediol, propanethiol, pentanediol, hexanediol, octanediol, decanediol
In a further preferred embodiment, the preparations according to the invention contain one or more fragrance substances or essences of group (d) selected from the group consisting of 3-phenylbutanal (oxalaldehyde), acetylmethylmethanol, 2-methyldecanal, 2-benzyl-2-methylbut-3-enenitrile (A), (B), (C
In the context of the present invention, the preparations according to the invention can be combined with other flavour or fragrance substances.
The invention therefore further provides a flavour or fragrance material comprising a formulation according to the invention and further flavour or fragrance materials of group (e) which may be added to a oleochemical or end product.
Perfume or Fragrance Materials of group (e) in the context of the present invention are those defined by e.g. european or american laws, such as the approved import bills of the european parliament and committee's regulations (EC) No 2232/96 and the committee's implementation regulations (EU) No 872/2012, and the substances listed by Steffen Arctander in "riechtoffe", Eigenverlag, montcalair, n.j.1969 in "Perfume and Flavor Chemicals" and h.surburg, j.panten,5th edition, Wiley-VCH, Weinheim 2006 in "Common Fragrance and Flavor Materials".
Examples of flavour and fragrance materials of group (e) in the context of the present invention are
Extracts of natural raw materials such as essential oils, extracts, absolutes, resins, resinoids, balms, tinctures such as, for example, ambergris tincture, sandalwood oil, angelica dahurica oil, angelica oil, anise oil, valerian oil, basil oil, moss-absolute, myrcia oil, wormwood oil, benzoin resin, spearmint oil, beeswax-absolute, birch tar oil, bitter almond oil, savory oil, cumin leaf oil, carnauba oil, juniper oil, calamus oil, camphor oil, ylang oil, cardamom oil, balsam oil, cassia oil, nutria-absolute, cedar leaf oil, cedar oil, labdane oil, citronella oil, lemon oil, copal balm, copal paste oil, coriander oil, vetiver oil, guanmu oil, cumin oil, cedar oil, dill oil, brave oil, linden oil, crambe oil, fennel oil, fenugreek oil, fen, Oak moss-absolute, elemi oil, tarragon oil, eucalyptus citriodora oil, eucalyptus globulus oil, fennel oil, spruce leaf oil, galbanum resin, geranium oil, grapefruit oil, guaiac oil, tomatillo oil, senecio oil, helichrysum-absolute, helichrysum oil, ginger oil, orris root-absolute, orris root oil, jasmine-absolute, acorus calamus oil, chamomile oil, roman chamomile oil, carrot seed oil, kale oil, pine needle oil, spearmint oil, caraway oil, labdanum oil, rosebush oil, rosa resin, lavandin oil, lavender absolute, lavender oil, lemongrass oil, angelica oil, distilled lime oil, squeezed lime oil, litsea cubeba oil, bay leaf oil, mace oil, marjoram oil, mandarin oil, mimosa oil, barr oil, baryota oil, barm oil, Musk seed oil, musk tincture, sage oil, nutmeg oil, myrrh absolute, myrrh oil, myrtle oil, clove leaf oil, clove flower oil, orange flower oil, frankincense absolute, frankincense oil, ledebouriella root oil, orange flower absolute, orange oil, oregano oil, palmarosa oil, patchouli oil, perilla oil, mirafragrance oil, parsley leaf oil, parsley seed oil, bitter orange leaf oil, peppermint oil, pepper oil, allspice oil, pine oil, Poley oil, rose absolute, rosewood oil, rose oil, rosemary oil, dammaraca oil, spanish tail oil, sandalwood oil, celery seed oil, lavender oil, anise oil, benzoin oil, marigold oil, cedar fir needle oil, tea tree oil, turpentine oil, thyme oil, Tuolu balsam, tonka absolute, jade-leaf oil, vanilla extract, violet oil, sage oil, tea tree oil, turpentine oil, thyme, Juniper oil, wine yeast oil, wormwood oil, wintergreen oil, ylang-ylang oil, ysop oil, civet absolute, cinnamon leaf oil, cinnamon bark oil, and fractions thereof, or components isolated therefrom;
lipids, such as ethyl butyrate, allyl caproate, benzyl acetate, methyl salicylate, neryl acetate, geranyl acetate, allyl caproate, anisic formate, butyl butyrate, butyl caproate, butylene phthalate, benzyl benzoate, citronellyl acetate, dimethyl anthranilate, ethoxyethyl acetate, ethyl butyrate, ethyl caprate, ethyl caproate, ethyl crotonate, ethyl isobutyrate, ethyl isovalerate, ethyl lactate, ethyl methyl butyrate, ethyl propionate, ethyl heptanoate, methyl dihydrojasmonate (e.g. ethyl butyrate, allyl caproate, benzyl acetate, butyl phthalate, methyl salicylate, benzyl benzoate, methyl anthranilate, dimethyl anthranilate, ethyl ethoxyethyl acetate, ethyl butyrate, ethyl caprate, ethyl caproate
alcohols, such as octenol, cis-3-hexanol, benzyl alcohol, phenethyl alcohol, eugenol, cis-3-hexenol, isoamyl alcohol, methyl butanol, 3, 1-methylthiohexanol, 2, 4-nonadienol, 2, 6-nonadienol, 2, 4-nonadienol, 2-octanol, 3-octanol, 1, 3-octenol, phenethyl alcohol, cinnamyl alcohol;
aldehydes, such as acetaldehyde, isobutyraldehyde, nonadienal, 3-phenylacetaldehyde, benzaldehyde, grapefruit aldehyde, isobutyraldehyde, 5-methylfurfural, paraldehyde, piperonal, propionaldehyde, vanillin, ethyl vanillin, isovanillin, phenylacetaldehyde, methylthiopropanal, cinnamaldehyde;
ketones, such as menthone, α -ionone, β -ionone, 4- (p-hydroxyphenyl) -2-butanone, 2-heptanone, 3-heptanone, 4-heptanone, p-hydroxybenzylacetone, 3,2, 2-methylcyclopentenone, 6,5, 2-methylheptanone, nootkatone, pentanedione, 4- (p-hydroxyphenyl) -2-butanone;
ethers such as 4-hydroxy-5-methylfuranone, 3-hydroxy-4, 5-dimethyl-2 (5H) -furanone, 2, 5-dimethyl-3-hydroxy-2 (3H) -furanone, 2(5) -ethyl-4-hydroxy-5 (2) -methyl-3 (2H) -furanone, p-methoxybenzaldehyde, guaiacol, methoxyvinylphenol, ethylfuranol, ethylguaiacol, isoeugenol methyl ether, menthol, 2, 5-dimethyl-4-hydroxy-3 (2H) furanone, soy sauce ketone (═ 2-ethyl-4-hydroxy-5-methyl-3 (2H) -furanone), High furanols (═ 2-ethyl-5-methyl-4-hydroxy-3 (2H) -furanone and 5-ethyl-2-methyl-4-hydroxy-3 (2H) -furanone, 1-dimethoxy-2, 2, 5-trimethyl-4-hexane;
aldehydes, e.g. acetaldehyde diethyl acetal, piperonal diethyl acetal
Lactones, such as ethylene brassylate,
terpenes, such as citronellol, nerol, lavender alcohol, farnesol, tetrahydrolinalool, tetrahydrogeraniol, 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 formates, acetates, propionates, isobutyrates, butyrates, isovalerates, valerates, caproates, crotonates, tiglates, 3-methyl-2-butenoates thereof;
-terpenes, such as geranial, neral, citronellal, 7-hydroxy-3, 7-dimethyloctanal, 7-methoxy-3, 7-dimethyloctanal, 2,6, 10-trimethyl-9-undecenal, the dimethyl and diethyl acetals of geranyl formate and geranial, neral and 7-hydroxy-3, 7-dimethylneo-aldehyde, menthol, isopulegol, α -terpineol, terpineol-4, menth-8-ol, menth-1-ol, menth-7-ol, borneol, isoborneol, linalool oxide, nopol, cedrol, ambroxol, vetiverol, guaiacol, and their formates, acetates, propionates, isobutyrates, butyrates, isovalerates, caproates, crotonates, tiglates, 3-methyl-2-butenoates;
-cyclic terpene alcohols, such as menthol, isopulegol, α -terpineol, terpineol-4, menth-8-ol, menth-1-ol, menth-7-ol, borneol, isoborneol, linalool oxide, nopol, cedrol, ambroxol, vetiverol, guaiacol, and their formates, acetates, propionates, isobutyrates, butyrates, isovalerates, valerates, caproates, crotonates, tiglates, 3-methyl-2-butenoate;
sulfides and disulfides, such as dimethyl sulfide, dimethyldisulfide, methylthiopropanal;
thiols, such as methylfuranthiol, benzothiazole, isopropylmethylthiazole, thiathiazole, 8, 3-thiomenthone, 4, 2-thiomethylpentanone, 2,4, 5-trimethylthiazole, 2-acetylthiazole, 2, 4-dimethyl-5-ethylthiazole;
pyrazines and pyrazolines, e.g. methylpyrazine, acetylpyrazine, 2-propionylpyrazine, 2-acetylpyrazoline, 2-acetyl-1-pyrazoline, 2-methyl-3-ethylpyrazine, 2-ethyl-3, 5-dimethylpyrazine, 2-ethyl-3, 6-dimethylpyrazine, 2, 3-diethyl-5-methylpyrazine, 3-isopropyl-2-methoxypyrazine, 3-isobutyl-2-methoxypyrazine, 2-pentylpyridylpyrazine
Alicyclic alcohols, such as α,3, 3-trimethylcyclohexylmethanol, 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) hexan-ol;
cyclic and cycloaliphatic ethers, such as cedarwood methyl ether, cyclododecyl methyl ether, (ethoxymethoxy) cyclododecane, α -cedrene epoxide, 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 ketones and macrocyclic ketones, for example 4-tert-butylcyclohexanone, 2, 5-trimethyl-5-pentylcyclopentanone, 2-heptylcyclopentanone, 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, 7-cyclohexadecen-1-one, 8-cyclohexadecen-1-one, 9-cyclohexadecen-1-one, cyclopentadecanone, 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, 1- (5, 5-dimethyl-1-cyclohexen-1-yl) -4-penten-1-yl, 2,3,8, 8-tetramethyl-1, 2,3,4,5,6,7, 8-octahydro-2-naphthylmethyl ketone, methyl 2,6, 10-trimethyl-2, 5, 9-cyclododecatrienyl ketone, tert-butyl 2, 4-dimethyl-3-cyclohexen-1-yl ketone;
esters of cyclic alcohols, for example 2-tert-butylcyclohexyl acetate, 4-tert-butylcyclohexyl acetate, 2-tert-amylcyclohexyl acetate, 4-tert-amylcyclohexyl acetate, decahydro-2-naphthyl acetate, 3-pentyltetrahydro-2H-pyran-4-yl acetate, decahydro-2, 5,5,8 a-tetramethyl-2-naphthyl acetate, 4, 7-methanol-3 a,4,5,6,7,7 a-hexahydro-5-or-6-indenyl propionate, 4, 7-methanol-3 a,4,5,6,7,7 a-hexahydro-5-or-6-indenyl isobutyrate, 4, 7-methanol-3 a,4,5,6,7,7 a-hexahydro-5-or-6-indenyl ester, 4, 7-methanolic octahydro-5-or-6-indenyl ester;
cycloaliphatic carboxylic esters, such as allyl 3-cyclohexylpropionate, allyl cyclohexyloxyacetate, cis-and trans-methyl dihydrojasmonate, cis-and trans-methyl jasmonate, methyl 2-hexyl-3-oxocyclopentanecarboxylate, ethyl 2-ethyl-6, 6-dimethyl-2-cyclohexenecarboxylate, ethyl 2,3,6, 6-tetramethyl-2-cyclohexenecarboxylate, ethyl 2-methyl-1, 3-dioxolane-2-acetate;
araliphatic alcohols, such as benzyl alcohol, 1-phenylethyl alcohol, 2-phenylethyl alcohol, 3-phenylpropyl alcohol, 2-phenoxyethanol, 2-dimethyl-3-phenylpropyl alcohol, 2-dimethyl-3- (3-methylphenyl) propanol, 1-dimethyl-2-phenylethyl alcohol, 1-dimethyl-3-phenylpropyl alcohol, 1-ethyl-1-methyl-3-phenylpropyl alcohol, 2-methyl-5-phenylpentanol, 3-phenyl-2-phenylalen-1-ol, 4-methoxybenzyl alcohol, 1- (4-isopropylphenyl) ethanol;
araliphatic ethers, for example 2-phenylethylmethyl ether, 2-phenylethylisoamyl ether, 2-phenylethyl 1-ethoxyethyl ether, phenylacetaldehyde dimethyl acetal, phenylacetaldehyde diethyl acetal, hydratropic aldehyde dimethyl acetal, phenylacetaldehyde glycerol acetal, 2,4, 6-trimethyl-4-phenyl-1, 3-dioxane, 4a,5,9 b-tetrahydroindeno [1,2-d ] -m-dioxin, 4a,5,9 b-tetrahydro-2, 4-dimethylindeno [1,2-d ] -m-dioxin;
aromatic and araliphatic aldehydes, such as benzaldehyde, phenylacetaldehyde, 3-phenylpropylaldehyde, hydratropic aldehyde, 4-methylbenzaldehyde, 3- (4-ethylphenyl) -2, 2-dimethylpropionaldehyde, 2-methyl-3- (4-isopropylphenyl) propanal, 2-methyl-3- (4-tert-butylphenyl) propanal, cinnamaldehyde, α -butylcinnamaldehyde, α -pentylcinnamaldehyde, α -hexylcinnamaldehyde, 3-methyl-5-phenylpentanal, 4-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 4-methoxyacetophenone, 4-tert-butyl-2, 6-dimethylacetophenone, 4-phenyl-2-butanone, 4- (4-hydroxyphenyl) -2-butanone, 1- (2-naphthyl) ethanone, benzophenone, 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-acetyl naphthalenone;
aromatic and araliphatic carboxylic acids and esters thereof, such as benzoic acid, phenylacetic acid, methyl benzoate, ethyl benzoate, hexyl benzoate, benzyl benzoate, methylphenyl acetate, ethylphenyl acetate, geranylphenyl acetate, phenylethyl phenylacetate, methyl cinnamate, ethyl cinnamate, benzyl cinnamate, phenylethyl cinnamate, allyl phenoxyacetate, methyl salicylate, isoamyl salicylate, hexyl salicylate, cyclohexyl salicylate, cis-3-hexenyl salicylate, benzyl salicylate, phenylethyl salicylate, methyl 2, 4-dihydroxy-3, 6-xylenate, ethyl 3-phenylglycidate, ethyl 3-methyl-3-phenylglycidate;
nitrogen-containing aromatic compounds, for example 2,4, 6-trinitro-1, 3-dimethyl-5-tert-butylbenzene, 3, 5-dinitro-2, 6-dimethyl-4-tert-butylacetophenone, cinnamonitrile, 5-phenyl-3-methyl-2-pentenenitrile, 5-phenyl-3-methylpentanenitrile, methyl aminobenzoate, methyl N-methylaminobenzoate, Schiff's salt of methyl anthranilate with 7-hydroxy-3, 7-dimethyloctanal, 2-methyl-3- (4-tert-butylphenyl) propanal or 2, 4-dimethyl-3-cyclohexenecarbaldehyde, 6-isopropylquinoline, 6-isobutylquinoline, 2, 4-dimethylcyclohexylamine, 2-tert-butylketone, 2-methyl-4-butenylaldehyde, 2-methyl-3-carba, 6-sec-butylquinoline, indole, skatole, 2-methoxy-3-isopropylpyrazine, 2-isobutyl-3-methoxypyrazine;
phenols, phenyl ethers and phenyl esters, for example methyl piperitol, eugenol, syringyl methyl ether, isoeugenol, isoeugenyl methyl ether, thymol, carvacrol, diphenyl ether, β -naphthyl methyl ether, β -naphthylethyl ether, β -naphthylisobutyl ether, 1, 4-dimethoxybenzene, eugenol acetate, 2-methoxy-4-methylphenol, 2-ethoxy-5- (1-propenyl) phenol, p-tolylphenyl acetate;
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;
and stereoisomers, enantiomers, positional isomers, diastereomers, cis/trans isomers or epimers of these substances (not explicitly mentioned here).
In a preferred embodiment, the flavour or fragrance composition is a liquid or solid flavour composition.
The invention further provides the use of the formulation according to the invention as a fine fragrance or perfume.
The invention further provides a substance mixture comprising
(a) One, two or more compounds selected from the group consisting of
(a1) An alcohol monoterpene of formula (I)
Wherein
R1 is H or methyl, R2 is H or C2-alkenyl and R3 is a straight-chain or branched, saturated or unsaturated hydrocarbon radical containing from 4 to 10 carbon atoms, and the enantiomers, diastereomers, racemates, solvates and physiologically compatible salts thereof,
and/or
(a2) The bicyclic epoxy monoterpene is a compound of the formula,
(b) at least two lactones of the formula (II)
Wherein
R4 is H or methyl, R5 is a straight-chain or branched, saturated or unsaturated hydrocarbon radical containing from 2 to 10 carbon atoms and n is 1 or 2, and enantiomers, diastereomers and racemates thereof,
(c) one, two or more solvents selected from the group consisting of
(c1) Ethanol and/or
(c2) One, two or more solvents selected from the group consisting of water, dipropylene glycol (DPG), diethyl phthalate (DEP), Propylene Glycol (PG), isopropyl myristate (IPM), isopropyl palmitate (IPP), triethyl citrate (TEC), Triacetin (TRI), 1, 2-propanediol, 1, 3-propanediol, propanethiol, pentanediol, hexanediol, octanediol, decanediolDodecanol, 4-hydroxyacetophenone (A), (B), (C
and optionally
(d) Other flavor materials or essences selected from the group consisting of 3-phenylbutanal (oxalaldehyde), acetylmethylmethanol, anethole acetate, dihydroeugenol, aryl formate, 2-methyldecanal, 2-benzyl-2-methylbut-3-enenitrile (A), (B), (C
It has surprisingly been found that the substance mixtures according to the invention are capable of reducing or masking the perceived intensity of unpleasant or unwanted off-flavours in various oleochemical formulations at very low concentrations, particularly when perceived by the test person as pungent, irritating, oxidising, irritating, rancid, fatty, animal, goat, fermented, mouldy, herbaceous and nauseous or odiferous, as demonstrated by the experimental data in table 2 of example 1.
Further, it has surprisingly been found that the substance mixture according to the invention functions even during use, even after elution of the substance mixture according to the invention or of the preparation containing the substance mixture according to the invention, as illustrated by the experimental data in tables 3 and 4 of example 1. For example, it has surprisingly been found that formulations containing the mixture of substances according to the invention are capable of masking unwanted odours, i.e. during hand or head washing and after elution, even in use, compared with equivalent amounts of typical perfuming formulations or perfumes.
It is evident that the substance mixtures according to the invention are particularly suitable for masking, covering or reducing unwanted off-flavours caused by aldehydes of the formula (III)
Wherein R6 is a saturated or unsaturated, linear hydroxyl group, preferably having a chain length of 3 to 10 carbon atoms.
And/or free fatty acids of formula (IV)
Wherein R7 is a straight-chain or branched, saturated hydroxyl group, preferably having a chain length of 3 to 12 carbon atoms.
It has surprisingly been found that the substance mixtures according to the invention or the combination of components (a), (b) and (c) and optionally component (d) have a synergistic activity. It is therefore evident that the combination according to the invention is significantly better able to mask unwanted off-notes (synergistic activity) than the substances of groups (a), (b) and (c) and optionally (d) alone, and better able to mask off-notes induced by the aldehydes of formula (III) or by the aldehydes of formula (III) and the free fatty acids of formula (IV) than the individual use, as demonstrated by the experimental data in table 2 of example 1.
The aldehydes of formula (III) and free fatty acids of formula (IV) are characterized or perceived as nasal, irritant, oxidative, irritating, rancid, fatty, animal, goat, fermentative, moldy, herbaceous and nauseous by the test subject.
It is evident that the substance mixtures according to the invention are particularly suitable for masking, covering or reducing unwanted off-flavours, which are initiated by the aldehydes of formula (III) and/or the free fatty acids of formula (IV).
Wherein the aldehydes of the formula (III) are selected from the group consisting of hexanal, heptanal, octanal, nonanal, decanal, hexenal, heptenal, octenal, nonenal, decenal, undecenal, dodecenal, adienal, heptadienal, octadienal, nonadienal, decadienal, undecenal, dodecenal, octenal, nontrienal, decatrienal, undecenal, dodecatrienal, dodecadienal, particularly preferably hexanal, octanal, nonanal, hexenal, heptenal, octenal, heptadienal, octadienal, decadienal and decatrienal,
and
the free fatty acids of formula (IV) are selected from the group comprising butyric, valeric, isovaleric, caproic, enanthic, caprylic, pelargonic, capric, undecanoic and dodecanoic acids, caproic, caprylic and capric acids being particularly preferred.
The present invention therefore further provides the use of a substance according to the invention for reducing and/or masking unwanted odours or off-flavours in oleochemical formulations.
The present invention therefore further provides the use of the substances according to the invention for reducing and/or masking unwanted odours or off-flavours in oleochemical formulations, in particular unwanted off-flavours caused by aldehydes of formula (III) and/or free fatty acids of formula (IV) as defined above.
In a preferred embodiment, the substance mixtures according to the invention contain at least two, three or four substances of group (a).
It is evident that the compounds linalool, geraniol, freesiol and nerolidol and enantiomers, diastereomers, racemates, solvates and physiologically compatible salts thereof are particularly suitable as component (a1) for masking unwanted off-tastes caused by aldehydes of the formula (III) and/or free fatty acids of the formula (IV), in particular by the specific aldehydes of the formula (III) and/or the specific free fatty acids of the formula (IV) as defined above.
In a preferred embodiment, the bicyclic epoxy monoterpene (ingredient (a2)) is an epoxy p-menthane derivative. It is also evident that the compounds 1, 4-cineole and 1, 8-cineole are particularly suitable as ingredient (a2) for masking unwanted off-flavours caused by aldehydes of formula (III) and/or free fatty acids of formula (IV), in particular caused by specific aldehydes of formula (III) and/or specific free fatty acids of formula (IV) as described above.
In a preferred embodiment, the substance mixtures according to the invention contain at least one compound of group (a1) and at least one compound of group (a2), wherein the compound of group (a1) is selected from the group consisting of linalool, geraniol, freesiol and nerolidol and the enantiomers, diastereomers, racemates, solvates and physiologically compatible salts thereof, and the compound of group (a2) is selected from the group consisting of 1, 4-cineole and 1, 8-cineole.
In another preferred embodiment of the substance mixtures according to the invention, the weight ratio of components (a1) and (a2) is from about 100:1 to about 1:100, preferably from about 50:1 to about 1:50, and particularly preferably from about 20:1 to about 1: 20.
For component (b), the substance mixtures according to the invention contain at least two, optionally three or four, lactones of the formula (II).
In a preferred embodiment, the substance mixtures according to the invention contain at least two, optionally three or four, lactones, selected from the group comprising lactones of the formula (II) and enantiomers, diastereomers and racemates thereof, wherein R4 is H, R5 is a straight-chain saturated hydrocarbon radical containing 2 to 10 carbon atoms, n is 1 or 2, particularly preferably R4 ═ H and R5 ═ a straight-chain saturated hydrocarbon radical containing 2 to 8 carbon atoms, and n ═ 1 or 2.
In a further preferred embodiment, the substance mixtures according to the invention contain at least two, optionally three or four, lactones selected from the group consisting of γ -dodecalactone, γ -decalactone, γ -undecalactone, δ -decalactone, δ -dodecalactone, 4-methyl- γ -nonalactone, 3-methyl- γ -decalactone, γ -nonalactone, δ -nonalactone, γ -octalactone, δ -octalactone, γ -heptalactone, δ -heptalactone, γ -caprolactone and δ -caprolactone, preferably γ -dodecalactone, γ -decalactone, δ -decalactone and δ -dodecalactone.
It is evident that γ -decalactone, δ -decalactone, γ -dodecalactone and δ -dodecalactone are particularly suitable as component (b) for masking unwanted off-flavours caused by aldehydes of formula (III) and/or free fatty acids of formula (IV), in particular caused by specific aldehydes of formula (III) and/or specific free fatty acids of formula (IV) as described above.
For component (c), it is apparent that ethanol and one, two or more selected from the group consisting of dipropylene glycol (DPG), diethyl phthalate (DEP), Propylene Glycol (PG), isopropyl myristate (IPM), isopropyl palmitate (IPP), triethyl citrate (TEC), Triacetin (TRI), 1, 2-propanediol, 1, 3-propanediol, propanethiol, pentanediol, hexanediol, octanediol, decanediol
For optional ingredient (d), it is obviously a combination of at least two, preferably at least three or four, groups (d) of flavor substances or essences which is advantageous for the particular use, in particular for further processing the substance mixture according to the invention into some end products. Thus, the mixtures according to the invention may contain at least two, three or four of the aforementioned flavor substances or essences of group (d).
In a further preferred embodiment, the substance mixtures according to the invention contain one or more fragrance substances or essences of group (d) selected from the group consisting of 3-phenylbutanal (oxalaldehyde), acetylmethylmethanol, 2-methyldecanal, 2-benzyl-2-methylbut-3-enenitrile (A), (B), (CB) 3-hexenyl acetate, styryl acetate, rhobafluoran, anther, prenyl acetate, styryl propionate, isoamyl phenylacetate, β -damascenone, isoamyl acetate, citronellol, and cyclohexyl acetate.
In a further preferred embodiment, the substance mixtures according to the invention are characterized by containing
(i)0.0000001 to 80% by weight of component (a),
(ii)0.0000001 to 80% by weight of component (b),
(iii)0.0000001 to 98% by weight of component (c), preferably 0.0000001 to 80% by weight, particularly preferably 0.0000001 to 75% by weight, particularly preferably 0.0000001 to 65% by weight,
(iv)0 to 80% by weight of component (d),
with the proviso that the quantitative data for the other optional constituents add up to 100% by weight, based on the total amount of the substance mixture.
In a further preferred embodiment, the substance mixture according to the invention is characterized in that it contains
(i)0.00001 to 50% by weight of component (a),
(ii)0.00001 to 80% by weight of component (b),
(iii)0.001 to 95% by weight of component (c), preferably 0.001 to 80% by weight, particularly preferably 0.001 to 75% by weight, and particularly preferably 0.001 to 65% by weight,
(iv)0 to 70% by weight of component (d),
with the proviso that the quantitative data for the other optional constituents add up to 100% by weight, based on the total amount of the substance mixture.
In a further preferred embodiment, the substance mixture according to the invention is characterized in that it contains
(i)0.001 to 40% by weight of component (a),
(ii)0.001 to 80% by weight of component (b),
(iii) from 0.01 to 95% by weight of component (c), preferably from 0.01 to 80% by weight, particularly preferably from 0.01 to 75% by weight, and particularly preferably from 0.01 to 65% by weight,
(iv)0 to 60% by weight of component (d),
with the proviso that the quantitative data for the other optional constituents add up to 100% by weight, based on the total amount of the substance mixture.
In a further preferred embodiment, the substance mixture according to the invention is characterized in that it contains
(i)0.1 to 40% by weight of component (a),
(ii)0.1 to 80% by weight of component (b),
(iii)0.1 to 90% by weight of component (c), preferably 0.1 to 80% by weight, particularly preferably.1 to 75% by weight, and particularly preferably 0.1 to 65% by weight,
(iv)0 to 50% by weight of component (d),
with the proviso that the quantitative data for the other optional constituents add up to 100% by weight, based on the total amount of the substance mixture.
It is clear that ethanol has a positive effect not only on the desired masking effect, but also on the further processing of the substance mixture according to the invention into the end product.
In a further embodiment of the substance mixtures according to the invention, the ethanol content is 30% by weight or less, more preferably 20% by weight or less, preferably 15% by weight or less, particularly preferably 10% by weight or less, based on the total amount of the substance mixture.
In a further preferred embodiment, the substance mixture according to the invention is characterized in that it contains
(i)0.0000001 to 80% by weight of component (a),
(ii)0.0000001 to 80% by weight of component (b),
(iii)0.0000001 to 98% by weight of component (c), preferably 0.0000001 to 80% by weight, particularly preferably 0.0000001 to 75% by weight, and particularly preferably 0.0000001 to 65% by weight,
(iv)0 to 80% by weight of component (d),
with the proviso that the ethanol (component c1) content is 30% by weight or less, more preferably 20% by weight or less, preferably 15% by weight or less, particularly preferably 10% by weight or less, based on the total amount of the substance mixture,
and is
The quantitative data with the other optional constituents add up to 100% by weight, based on the total amount of the substance mixture.
In a further preferred embodiment, the substance mixture according to the invention is characterized in that it contains
(i)0.00001 to 50% by weight of component (a),
(ii)0.00001 to 80% by weight of component (b),
(iii)0.001 to 95% by weight of component (c), preferably 0.001 to 80% by weight, particularly preferably 0.001 to 75% by weight, and particularly preferably 0.001 to 65% by weight,
(iv)0 to 70% by weight of component (d),
with the proviso that the ethanol (component c1) content is 30% by weight or less, more preferably 20% by weight or less, preferably 15% by weight or less, particularly preferably 10% by weight or less, based on the total amount of the substance mixture,
and is
The quantitative data with the other optional constituents add up to 100% by weight, based on the total amount of the substance mixture.
In a further preferred embodiment, the substance mixture according to the invention is characterized in that it contains
(i)0.001 to 40% by weight of component (a),
(ii)0.001 to 80% by weight of component (b),
(iii) from 0.01 to 95% by weight of component (c), preferably from 0.01 to 80% by weight, particularly preferably from 0.01 to 75% by weight, and particularly preferably from 0.01 to 65% by weight,
(iv)0 to 60% by weight of component (d),
provided that
The ethanol (component c1) content is 30% by weight or less, more preferably 20% by weight or less, preferably 15% by weight or less, particularly preferably 10% by weight or less, based on the total amount of the substance mixture,
and is
The quantitative data with the other optional constituents add up to 100% by weight, based on the total amount of the substance mixture.
In a further preferred embodiment, the substance mixture according to the invention is characterized in that it contains
(i)0.1 to 40% by weight of component (a),
(ii)0.1 to 80% by weight of component (b),
(iii)0.1 to 90% by weight of component (c), preferably 0.1 to 80% by weight, particularly preferably 0.1 to 75% by weight, and particularly preferably 0.1 to 65% by weight,
(iv)0 to 50% by weight of component (d),
provided that
The ethanol (component c1) content is 30% by weight or less, more preferably 20% by weight or less, preferably 15% by weight or less, particularly preferably 10% by weight or less, based on the total amount of the substance mixture,
and is
The quantitative data with the other optional constituents add up to 100% by weight, based on the total amount of the substance mixture.
In another preferred embodiment of the substance mixture according to the invention, the weight ratio of components (a) and (b) is from about 100:1 to about 1:100, preferably from about 50:1 to about 1:50, and particularly preferably from about 1:20 to about 20: 1.
In a further embodiment of the substance mixtures according to the invention, the weight ratio of the components (a + b) and (c) is from about 100:1 to about 1:100, particularly preferably from about 50:1 to about 1:50, and particularly preferably from about 30:1 to 1: 30.
In a preferred embodiment, the substance mixture according to the invention is a liquid mixture. However, it can be converted into a solid formulation, for example by spray drying.
The present invention therefore further provides a process for preparing the abovementioned substance mixtures according to the invention, comprising the steps of:
i) mixing (a), (B), (c) and optionally (d), wherein components (a) to (d) are present in the form of solids, solutions, extracts, aqueous extracts and enriched preparations or concentrates, for example by distillation, chromatography or the methods disclosed in EP 2075321B 1,
and optionally
ii) spray drying the substance mixture thus obtained.
In the context of the present invention, the substance mixtures according to the invention can be combined with other additional flavour or fragrance substances.
The present invention therefore further provides a flavour or fragrance material comprising a mixture of materials according to the invention in combination with additional flavour or fragrance materials of group (e) capable of being added to an oleochemical or end product.
For the additional flavour or fragrance materials of group (e), the above description applies.
In a preferred embodiment, the flavor composition or mixture of flavors is a liquid or solid flavor composition.
The present invention therefore further provides a process for the production of the above flavour or fragrance composition comprising the steps of:
i) mixing (a), (B), (c) and optionally (d), wherein components (a) to (d) are present in the form of solids, solutions, extracts, aqueous extracts and enriched preparations or concentrates, for example by distillation, chromatography or the methods disclosed in EP 2075321B 1,
and optionally
ii) spray drying the substance mixture thus obtained.
The present invention therefore further provides the use of a flavour or fragrance composition as described above for reducing and/or masking unwanted off-flavours in oleochemical formulations, in particular unwanted off-flavours caused by aldehydes of formula (III) and/or free fatty acids of formula (IV) as described above.
In the context of the present invention, the substance mixtures according to the invention can be used in the desired products with the aim of masking unpleasant odours or tastes caused by the aldehydes of the formula (III) and/or the free fatty acids of the formula (IV) or replacing these odours or tastes with odours which are perceived as pleasant. Typical examples of products which can be used with the substance mixtures according to the invention are, for example, soap substrates, washing powders, dishwashing liquids and detergents and cosmetic preparations. The substance mixtures according to the invention are preferably used in amounts of 0.0001 to 3 wt.%, preferably 0.001 to 1.5 wt.%, particularly preferably 0.01 to 1.2 wt.%, particularly preferably 0.01 to 1 wt.%, based on the formulation or the end product.
The present invention therefore further provides formulations, in particular oleochemical formulations, or end products, which contain the substance mixtures according to the invention or the above-described flavour or flavour compositions containing the substance mixtures according to the invention and further flavour or flavour substances of group (e).
Thus, the invention also provides a formulation comprising
(i) The above-mentioned substance mixtures according to the invention,
and
(ii) aldehydes of the formula (III)
And/or
(iii) Free fatty acids of formula (IV).
In a preferred embodiment, the formulation is an oleochemical.
In a preferred embodiment, the oleochemical or the final mixture is selected from the group consisting of detergents, washing powders, air fresheners, candles, dishwashing liquids, fabric softeners, skin creams, lip care products, make-up removers, conditioners, lotions, shampoos, body washes, and soaps and solid and liquid embodiments thereof, with shampoos, body washes, soaps and solid and liquid embodiments thereof being particularly preferred
The present invention therefore also provides the use of a mixture of substances according to the invention or of a fragrance or fragrance composition as described above containing a mixture of substances according to the invention and further fragrances or fragrance substances of group (d) for reducing and/or masking unwanted odours or off-notes in oleochemical formulations selected from the group comprising detergents, washing powders, air fresheners, candles, dishwashing liquids, fabric softeners, skin creams, lip care products, make-up removers, hair conditioners, lotions, shampoos, body washes and soaps and solid and liquid embodiments thereof, in particular unwanted off-notes caused by the aldehydes of formula (III) and/or free fatty acids of formula (IV).
The invention also provides formulations comprising the abovementioned substance mixtures or flavor or fragrance compositions according to the invention and aldehydes of the formula (III) and/or free fatty acids of the formula (IV).
The end product may contain from 0.0001% to 3% by weight, preferably from 0.001% to 1.5% by weight, particularly preferably from 0.01% to 1.2% by weight, and particularly preferably from 0.01% to 1% by weight, of the formulation, based on the end product.
In another embodiment, the formulation contains ingredients (a) and (b), or (a) and (c) or (a) and (c + b) in a weight ratio of 1:0.00001 to 1:120, preferably 1:0.001 to 1:100, especially 1:0.01 to 1: 50.
The end product containing the formulation is selected from the group consisting of detergents, washing powders, air fresheners, candles, dishwashing liquids, fabric softeners, skin creams, lip care products, make-up removers, conditioners, lotions, shampoos, body washes and soaps and solid and liquid embodiments thereof, preferably soaps and solid and liquid embodiments thereof, shampoos and body washes, and particularly preferably soaps and solid and liquid embodiments thereof.
Likewise, the present invention further provides the use of the substance mixture according to the invention or of the above-mentioned flavor or flavor composition as a fine flavor or perfume.
Industrial applicability
According to the invention, mixtures of substances, flavor or fragrance compositions and formulations can be prepared which can be used to reduce and/or mask unwanted off-flavours in formulations, in particular oleochemical formulations.
The invention further provides the use of the aforementioned substance mixtures, fragrance compositions and formulations for the preparation of intermediate and end products selected from the group consisting of perfumes, detergents, washing powders, air fresheners, candles, dishwashing liquids, fabric softeners, skin creams, lip care products, make-up removers, conditioners, lotions, shampoos, body washes and soaps and solid and liquid embodiments thereof, preferably soaps and solid and liquid embodiments thereof, shampoo and body washes, particularly preferably soaps and solid and liquid embodiments thereof.
Examples
The invention will be more readily understood by reference to the following examples. However, the examples are only for illustrating the present invention and are not to be construed as limiting the scope of the present invention.
Unless otherwise indicated, the data are based on weight.
For the preparation of soap samples 1 to 7, phase B, which corresponds to substance mixture 1 according to the invention, was premixed. The components of phase A and the premixed phase B are mixed in a kneader. The resulting mass was molded into a block using an extruder. Subsequently, it was left to stand at room temperature for 7 days.
Phase B of bars 1-4 and 6-7 are not according to the invention, since they do not contain all of the components (a) to (c) required according to the invention. Thus, phase B of bar 1 contains only component (c), phase B of bar 2 contains only components (B) and (c), phase B of bar 3 contains component (c), phase B of bar 4 contains components (a) and (c), phase B of bar 6 contains components (B), (c) and (e), and bar 7 contains components (a) and (c).
Phase B of bar 5 is a mixture of substances according to the invention, which contains the desired components (a) to (c).
The resting blocks were coded and evaluated organoleptically by 15 experts. Including determining the overall intensity of perception and the perceived intensity of unwanted off-flavours and a description of the olfactory impression. The measured values were compared to soap sample 1 and percent odor intensity was calculated based on bar 1.
Sensory measurements for bars 1 to 7 are given in table 2:
further, the olfactory impression of the different soap bars 1 to 7 was determined during use. To do this, one hand is cleaned with bar 1 and the other hand is cleaned with a different bar. The expert panel then evaluates the soapy hand and the wet hand after washing with water, respectively, and gives again the perceived overall intensity, the odor intensity and a description. Sensory evaluations are listed in tables 3 and 4.
The results show that the combination of geraniol (component (a)), lactone (component (b)), and solvents EtOH and DPG (component (c)) in bar 5 according to the invention has significantly smaller values in perceived odor intensity than the use of these materials alone. This synergistic effect was found during all the processes used and these substances were shown to be more active than the others. Further, such an effect may also occur at a low concentration or usage amount.
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