Use of polyhydroxyaromatic compounds for treating amino acid-based fibrous substrates

Abstract

The present invention relates to the use of polyhydroxyaromatic compounds for treating amino acid-based fibrous substrates, preferably hair, novel polyhydroxyaromatic compounds, aqueous compositions comprising said polyhydroxyaromatic compounds, cosmetic compositions, in particular hair care compositions, comprising said polyhydroxyaromatic compounds, and methods for treating hair comprising using said cosmetic compositions.

Description

SUMMARY OF THE INVENTION

[0001] The present invention relates to the use of polyhydroxyaromatic compounds for treating amino acid-based fibrous substrates, preferably hair, novel polyhydroxyaromatic compounds, aqueous compositions comprising said polyhydroxyaromatic compounds, cosmetic compositions, in particular hair care compositions, comprising said polyhydroxyaromatic compounds, and methods for treating hair using said cosmetic compositions. TECHNICAL FIELD

[0002] The present invention relates to the use of polyhydroxyaromatic compounds and aqueous compositions comprising them for treating amino acid-based fibrous substrates, preferably hair, especially human hair and animal hair, more particularly human hair. Also of further interest are long-term storage-stable aqueous compositions for delivering and attaching said polyhydroxyaromatic compounds to human hair for permanent shaping and coloring purposes. BACKGROUND OF THE INVENTION

[0003] Hair can generally be straight, wavy, curly, kinky or coiled. Human hair comprises three main morphological components, namely the cuticle (the outermost thin shell of several concentric layers), the cortex (the body of the hair), and, in the case of higher diameter hair, the medulla (the thin central core). The cuticle and the cortex provide the mechanical properties of the hair strand, i.e., its tendency to be wavy, curly or kinky. A straight hair strand can resemble a rod with a circular cross-section, a wavy hair strand can appear compressed into an oval cross-section, a curly strand can appear further compressed into an elongated elliptical cross-section, and a coiled hair strand cross-section can be even flatter. The main component of hair is cross-linked α-helical protein keratin. Keratin is an intermediate filament protein found especially in epithelial cells such as human skin and hair, wool, feathers, and nails. The α-helical type I and II keratin intermediate filament proteins (KIF) with a molecular weight of about 45 - 60 kDa are embedded in an amorphous matrix of keratin-associated proteins (KAP) with a molecular weight between 20 - 30 kDa (M.A. Rogers, L. Langbein, S. Praetzel-Wunder, H. Winter, J. Schweizer, J. Int Rev Cytol. 2006; 251:209 - 6); both intramolecular and intermolecular disulfide bonds provided by cystine contribute to maintaining the cytoskeletal protein network of the cell scaffold. In addition to disulfide cross-links, ionic bonding or salt bridges pairing various amino acids found in hair proteins also contribute to the shape of the hair strand.

[0004] It is well known in the art that hair can be treated with functionalized silicones that provide one or more cosmetic benefits such as conditioning, color retention, shine, and UV protection. Typically, these silicones physically deposit on the surface of the fiber (cuticle) and are thus responsible for the appearance of the hair. They can be partially or completely removed by repeated washing processes. Although the deposited silicones greatly improve the surface properties of the hair, namely smoothness (slipperiness) and friction, they essentially do not affect the mechanical properties and shape of the fiber.

[0005] Individuals with naturally wavy, curly, or kinky hair may desire to reduce frizz and achieve more control and a smoother appearance of their hair. Several hair treatments, including straightening methods, are available, but these often involve the use of harsh and regulated substances.

[0006] Frequently used straightening preparations are based on sodium or potassium hydroxide blended with starch, which is highly irritating to the scalp. Less irritating formulations are based on guanidine hydroxide or certain sulfites. More recent formulations are based on thioglycolates. The basic principle is that under alkaline conditions, the disulfide bonds within the hair proteins undergo reductive cleavage. The disulfide bonds are reduced to sulfhydryl groups and, after shaping, the desired hair configuration is re-established by oxidation.

[0007] The different methods for straightening hair have a tendency to weaken the hair strength. Therefore, there is a desire to find compositions that enable the hair to be straightened and restore the strength and elasticity of the hair. Traditionally, aldehyde-based formulations have been developed for permanent hair shaping. Formaldehyde is most commonly used for the so-called Brazilian keratin shaping method (US 2012-0031420). The basic principle is a crosslinking reaction between formaldehyde and keratin-based amino and amido groups (H. Puchtler, HistOCHemistry, 82 (1985), pp. 201-204) or a crosslinking reaction between formaldehyde and -SH groups (US 2009-0211593) after straightening. Glyoxal, a dialdehyde, has been proposed as an alternative to formaldehyde (US 2009-0165812). The inventors of the present invention were searching for alternative, non-irritating compounds to replace the critical formaldehyde treatment.

[0008] Polyhydroxy aromatic compounds containing glycerol derivatives are known. The synthesis of mono-, di- and tri-galloyl glycerols is described in US 1927339. The starting points are the corresponding mono-, di- and trichloro derivatives of glycerol. Mono-galloyl glycerol is known as an antioxidant (Z. Song, Z. Xiao, Linchan Huaxue Yu Gongye (1988), 8(3), 9-18). Mono-galloyl dioleoyl glycerol causes weight loss in rats (T. Nagao, T. Sayuri, T. Tatsuya, M. Yukari, S. Hideaki Journal of Oleo Science (2011), 60(9), 457-62). Poly-galloyl derivatives, namely hexagalloyl sorbitol, pentagalloyl glucose and trigalloyl glycerol, are proposed in tannin compositions (WO 9218457). Galloyl diglucosides are components in hair care formulations for reducing hair damage (JP 2004210724). The natural-derived tannin, tannic acid, which is a complex poly-galloyl ester of glucose, is used in hair dyeing formulations (US4981485).

[0009] WO2016046178 discloses polyhydroxy aromatic organosilicons for treating hair.

[0010] None of the above prior art disclosures describe a simple method for a defined hydrocarbon galloyl derivative where the backbone chain can be flexibly adjusted over a wide range. In addition, none of the prior art describes a method for producing a composition that is long-term stable, easy to prepare and easy to use, which contains these defined galloyl hydrocarbon derivatives and is additionally robust to the presence of other performance ingredients and provides hair strengthening benefits and hair coloring benefits without using strongly irritating aids. Summary of the Invention

[0012] According to the present invention, there is provided the use of a compound of the following formula for treating an amino acid-based fibrous substrate, preferably hair:

[0013] R 2 (–F) 2-18

[0014] wherein

[0015] R 2 is selected from optionally substituted divalent to octadeca-valent hydrocarbon groups, preferably aliphatic hydrocarbon groups, having up to 100 carbon atoms and optionally containing one or more groups selected from: –O–, –NH–, –C(O)–, –C(S)–, tertiary amino groups and quaternary ammonium groups and

[0016] F is selected from:

[0017] –O–C(O)–R 3 –R 4 and

[0018] –NR 1 –C(O)–R 3 –R 4 ,

[0019] (preferably F is selected from –O–C(O)–R 3 –R 4 ),

[0020] group F is attached to the carbon atom of R 2 wherein

[0021] wherein

[0022] R 1 is selected from hydrogen or an optionally substituted straight-chain, cyclic or branched, saturated, unsaturated or aromatic hydrocarbon group having up to 100 carbon atoms and optionally containing one or more groups selected from: –O–, –NH–, –C(O)–, –C(S)–, tertiary amino groups and quaternary ammonium groups

[0023] R 3 is selected from a single bond or an optionally substituted straight-chain, cyclic or branched, saturated, unsaturated or aromatic hydrocarbon group having up to 100 carbon atoms and optionally containing one or more groups selected from: –O–, –NH–, –C(O)–, –C(S)–, tertiary amino groups and quaternary ammonium groups preferably R 3 is a single bond or an ethenylene group, and

[0024] R 4 is selected from di- and tri-hydroxy substituted aromatic groups

[0025] wherein the compound excludes tannins.

[0026] The use also relates to: a method for treating hair, which comprises applying the compound to the hair; in particular a method for cosmetic treatment of hair.

[0027] The claimed use or method does not include the use of tannins as the compound, although the use of the compound in combination with tannins is covered by the scope of the present invention. According to Karamali Khanbabaee and Teunis van Ree, Nat. Prod. Rep., 2001, 18, 641–649 “Tannins: Classification and Definition”, tannins are “polyphenolic secondary metabolites of higher plants and are galloyl esters and their derivatives, where the galloyl moiety or their derivatives are attached to various polyol-, catechol- and triterpenoid nuclei (gallotannins, ellagitannins and complex tannins), or they are oligomeric and polymeric proanthocyanidins (condensed tannins) which may have different interflavanyl coupling and substitution patterns”. Such tannins are excluded from the scope of the compounds of the formula R 2 (–F) 2-18 of the compound.

[0028] Group F is:

[0029] *–O–C(O)–R 3 –R 4 , and

[0030] *–NR 1 –C(O)–R 3 –R 4 ,

[0031] where the bond marked with an asterisk is attached to the carbon atom of R 2 and is exemplified as follows:

[0032] C*–O–C(O)–R 3 –R 4 , and

[0033] C*–NR 1 –C(O)–R 3 –R 4 .

[0034] The preferred group F is –O–C(O)–R 3 –R 4 .

[0035] In a preferred embodiment of the present invention, R 4 , i.e., a di- and tri-hydroxy substituted aromatic group, is a group of the following formula:

[0036]

[0037] where R 10 , R11 , R 12 , R 13 , R 14 are independently selected from hydroxy or R 1 , preferably R 1 is hydrogen, provided that R 10 -R 14 2-3 groups of which are hydroxy, and wherein the dashed line represents a bond to R 3 , or, when R 3 is a single bond, is R 3 ; or R 4 is selected from di- and tri-hydroxy-substituted naphthyl groups.

[0038] Particularly preferred groups R 4 are selected from dihydroxyphenyl groups such as 2,3-dihydroxyphenyl, 2,4-dihydroxyphenyl, 2,5-dihydroxyphenyl, 2,6-dihydroxyphenyl, 3,4-dihydroxyphenyl and 3,5-dihydroxyphenyl, trihydroxyphenyl groups such as 2,3,4-trihydroxyphenyl, 2,3,5-trihydroxyphenyl, 2,3,6-trihydroxyphenyl, 2,4,5-trihydroxyphenyl, 2,4,6-trihydroxyphenyl and 3,4,5-trihydroxyphenyl; dihydroxynaphthyl groups such as 6,7-dihydroxynaphthyl, 5,6-dihydroxynaphthyl, 1,7-dihydroxynaphthyl, 3,7-dihydroxynaphthyl, 1,3-dihydroxynaphthyl and 1,4-dihydroxynaphthyl, and trihydroxynaphthyl groups such as 4,6,7-trihydroxynaphthyl and 1,5,6-trihydroxynaphthyl. Most preferred is 3,4,5-trihydroxyphenyl.

[0039] In a preferred embodiment of the present invention, R 4Derived from polyhydroxyaromatic carboxylic acids, such as poly (i.e., di- and trihydroxy) hydroxybenzoic acids, such as dihydroxybenzoic acids such as 2,3-dihydroxybenzoic acid, 2,4-dihydroxybenzoic acid, 2,5-dihydroxybenzoic acid, 2,6-dihydroxybenzoic acid, 3,4-dihydroxybenzoic acid, and 3,5-dihydroxybenzoic acid, or trihydroxybenzoic acids such as 2,3,4-trihydroxybenzoic acid, 2,3,5-trihydroxybenzoic acid, 2,3,6-trihydroxybenzoic acid, 2,4,5-trihydroxybenzoic acid, 2,4,6-trihydroxybenzoic acid, and 3,4,5-trihydroxybenzoic acid; polyhydroxycinnamic acids, such as dihydroxycinnamic acids such as 3,4-dihydroxycinnamic acid, or trihydroxycinnamic acids such as 3,4,5-dihydroxycinnamic acid; polyhydroxynaphthalene carboxylic acids, such as dihydroxynaphthalene carboxylic acids such as 6,7-dihydroxynaphthalene-2-carboxylic acid, 5,6-dihydroxynaphthalene-2-carboxylic acid, 1,7-dihydroxynaphthalene-2-carboxylic acid, 3,7-dihydroxynaphthalene-2-carboxylic acid, 1,3-dihydroxynaphthalene-2-carboxylic acid, and 1,4-dihydroxynaphthalene-2-carboxylic acid, or trihydroxynaphthalene carboxylic acids such as 4,6,7-trihydroxynaphthalene-2-carboxylic acid, and 1,5,6-trihydroxynaphthalene-2-carboxylic acid. Most preferred is 3,4,5-trihydroxybenzoic acid (gallic acid).

[0040] Here and in the context of the present invention, "derived from" shall mean, in particular, a residue formally formed from a compound by reacting these compounds to obtain the compounds of the present invention. For example, consider the case where R 4 is derived from a polyhydroxyaromatic carboxylic acid, in which case R derived from a polyhydroxyaromatic carboxylic acid 4 will be obtained, for example, by reacting a polyol or polyepoxide of the following formula with a polyhydroxyaromatic carboxylic acid H–O–C(O)–R 3 –R 4 in a reaction:

[0041] R 2 (–A) c

[0042] to form, for example,

[0043] R 2 (–OH) a (–O–C(O)–R 3 –R 4 ) b

[0044] where A is an OH and / or epoxy group, preferably an epoxy group: and where c = 2-18, preferably c = 2-10, more preferably c = 2-8, more preferably c = 2-4,

[0045] where b≥2 and a + b = 2 - 18, preferably b = 2 - 6, more preferably b = 2 - 4, still more preferably b = 2, and a + b = preferably 2 - 8, more preferably a + b = 2 - 6,

[0046] and correspondingly, R derived from a polyhydroxyaromatic carboxylic acid 4 will be a di - or tri - hydroxy - substituted aromatic group, and R 3 is a single bond.

[0047] In a preferred embodiment of the present invention, the optional substituents of the group R 1 , R 2 and R 3 are selected from hydroxy, amino and halogen, preferably hydroxy and amino, and the number of substituents can be up to 5, preferably 1 - 4.

[0048] In a preferred embodiment of the present invention, R 1 is selected from hydrogen; n -, iso - or tert - C1 - C 22 - alkyl, C2 - C 22 - alkoxyalkyl, C5 - C 30 - cycloalkyl, C6 - C 30 - aryl, C6 - C 30 - aryl(C1 - C6)alkyl, C6 - C 30 - alkylaryl, C2 - C 22 - alkenyl, C2 - C 22 - alkenyloxyalkyl, which may optionally be each substituted by hydroxy and halogen, and which may optionally contain one or more ether groups (–O–); preferably hydrogen or n -, iso - or tert - C1 - C 22 - alkyl. Most preferably, R 1 is hydrogen.

[0049] In a preferred embodiment of the present invention, R 2 is selected from divalent to decavalent, more preferably divalent to hexavalent, still more preferably divalent hydrocarbon groups having 2 - 30 carbon atoms, more preferably 2 - 20 carbon atoms, even more preferably 2 - 15 carbon atoms and which may optionally contain one or more groups selected from –O–, –NH–, –C(O)–, –C(S)–, preferably aliphatic hydrocarbon groups, and wherein R 2 may optionally be substituted by one or more hydroxy groups.

[0050] In a preferred embodiment of the present invention, R 2 has a valence of 2 - 18, preferably 2 - 12, more preferably 2 - 10, and still more preferably 2 - 8, such as 2 - 6, especially 2 or 3 or 4.

[0051] In a preferred embodiment of the present invention, R2 Selected from R 2 ’, R 2 ’ is selected from:

[0052] - divalent to octadecavalent, preferably divalent to hexavalent, more preferably divalent hydrocarbon groups as follows: derived from aliphatic polyols having more than three carbon atoms such as alkane di-, tri- and tetraols such as 1,6 - hexanediol, trimethylolpropane, and pentaerythritol,

[0053] - divalent to octadecavalent, preferably divalent to hexavalent, more preferably divalent hydrocarbon groups including at least one ether group and optionally having one or more hydroxyl substituents as follows: derived from polyalkylene oxides such as polyethers based on ethylene oxide, propylene oxide and / or butylene oxide, for example derived from polyglycols such as diethylene glycol, triethylene glycol, tetraethylene glycol, and pentaethylene glycol, etc., or derived from polypropylene glycol such as dipropylene glycol (e.g., derived from 2,2′ - oxydi - 1 - propanol, 1,1′ - oxydi - 2 - propanol, and 2 - (2 - hydroxypropoxy) - 1 - propanol), tripropylene glycol, tetrapropylene glycol, pentapropylene glycol, etc., derived from copolymers based on a mixture of ethylene oxide and butylene oxide, derived from copolymers based on a mixture of propylene oxide and butylene oxide, and derived from copolymers based on a mixture of ethylene oxide and propylene oxide and butylene oxide,

[0054] - divalent to octadecavalent, preferably divalent to hexavalent, more preferably divalent hydrocarbon groups optionally including at least one ether group and optionally having one or more hydroxyl substituents as follows: derived from oligoglycerols such as diglycerol, triglycerol, tetraglycerol, pentaglycerol, hexaglycerol, and statistically distributed glycerol oligomeric condensation products, such as

[0055] - divalent to octadecavalent, preferably divalent to hexavalent, more preferably divalent hydrocarbon groups as follows: derived from compounds including at least one glycidyloxy group, such as diglycidyl ether, glycerol diglycidyl ether, and glycerol triglycidyl ether,

[0056] - divalent to octadecavalent, preferably divalent to hexavalent, more preferably divalent hydrocarbon groups including at least one ether group and optionally having one or more hydroxyl substituents as follows: derived from polyol alkylene oxide addition products, such as addition products of ethylene oxide and / or propylene oxide to polyols such as ethylene glycol, 1,2 - propanediol, glycerol, trimethylolpropane, pentaerythritol, sorbitol, and sucrose,

[0057] - A divalent to octadecavalent, preferably divalent to hexavalent, more preferably divalent hydrocarbon group containing at least one ether group and optionally having one or more hydroxyl and / or amino substituents: It is derived from a polyamine alkylene oxide addition product, such as the addition product of ethylene oxide and / or propylene oxide to ethylenediamine, diethylenetriamine, or the addition product of alkylene oxide to ethanolamine.

[0058] - A divalent to octadecavalent, preferably divalent to hexavalent, more preferably divalent hydrocarbon group containing at least one ester group and having one or more hydroxyl substituents: It is derived, for example, from a polyester, preferably from the condensation of a divalent to hexavalent carboxylic acid such as maleic acid, succinic acid, adipic acid, sebacic acid, itaconic acid, tartaric acid, trimellitic acid with an alkylene oxide such as ethylene oxide, propylene oxide, butylene oxide, and a compound containing at least one glycidyloxy group such as glycidol, diglycidyl ether, glycerol diglycidyl ether, glycerol triglycidyl ether, especially the condensation product of succinic acid, maleic acid, and tartaric acid with glycerol diglycidyl ether.

[0059] - Further, R 2 ’ preferably represents a polyalkyleneoxy group, which preferably has the following general formula:

[0060] -[CH2CH2O] q1 -[CH2CH(CH3)O] r1 -[CH2CH(C2H5)O] s1 -{[CH2CH2] q2 -[CH2CH(CH3)] r2 -[CH2CH(C2H5)] s2}-

[0061] where

[0062] q1 = 0 - 49, preferably 0 - 10, more preferably 1 - 10, even more preferably 1 - 5,

[0063] r1 = 0 - 32, preferably 0 - 10, more preferably 1 - 10, even more preferably 1 - 5,

[0064] s1 = 0 - 24, preferably 0 - 10, more preferably 1 - 10, even more preferably 1 - 5,

[0065] q2 = 0 or 1,

[0066] r2 = 0 or 1,

[0067] s2 = 0 or 1, and

[0068] ∑(q2 + r2 + s2) = 1,

[0069] The condition is that the sum of the carbon atoms in the polyalkylene oxide group is 2 - 100, preferably 2 - 50, more preferably 2 - 30, even more preferably 2 - 20, especially 2 - 15.

[0070] - A divalent hydrocarbon group derived from oligoglycerol of the following general formula:

[0071] -[CH2CH(R 7 )CH2O] t1 -[CH2CH(R 7 )CH2)] t2 -

[0072] where

[0073] t1 = 0 - 32, preferably 0 - 10, more preferably 1 - 10, even more preferably 1 - 5, especially 1 and 2,

[0074] t2 = 1,

[0075] R 7 = OH or F, where F is as defined above, preferably –O–C(O)–R 3 –C(O)OH,

[0076] The condition is that the sum of the carbon atoms is 2 - 100, preferably 2 - 50, more preferably 2 - 30, even more preferably 2 - 20, especially 2 - 15, and

[0077] - A divalent hydrocarbon group containing at least one ester group of the following general formula:

[0078] -[CH2CH2O] q1 -R 8 -[CH2CH2O] q1 -[CH2CH2] q2 -

[0079] where q1 can be the same or different and is as defined above, and q2 = 1

[0080] and

[0081] -[CH2CH(R 7 )CH2O] t1 -R 8 -[CH2CH(R 7 )CH2O] t1 -[CH2CH(R 7 )CH2)] t2 -

[0082] where t1, t2 and R 7 are as defined above, and

[0083] R 8Selected from -C(O)C(O)O-; -C(O)(CH2) 1-8 C(O)O-, which is derived, for example, from succinic acid, pimelic acid, sebasic acid; or -C(O)(C6H4)C(O)O-, i.e., it is derived from phthalic acid and terephthalic acid; -C(O)CH=CHC(O)O-, -C(O)C(=CH2)-CH2C(O)O-, -C(O)CH(OH)CH(OH)C(O)O-,

[0084] provided that the sum of the carbon atoms in R 2 ’ is 2 - 100, preferably 2 - 50, more preferably 2 - 30, even more preferably 2 - 20, especially 2 - 15.

[0085] In a preferred embodiment of the present invention, R 2 (or R 2 ’ as mentioned above or below, or R 2 ”) contains one or more, for example, 1 - 5 groups –O–. These groups –O– are preferably ether groups, but can also form ester groups together with carbonyl groups. Preferably, these groups R 2 (or R 2 ’ as mentioned above or below, or R 2 ”) are substituted by one or more hydroxyl groups.

[0086] In a preferred embodiment of the present invention, the compound used according to the present invention has the following formula:

[0087]

[0088] wherein R 5 is selected from hydroxyl or F, where F is as defined above, provided that at least two of R 5 are F.

[0089] In a preferred embodiment of the present invention, the compound used according to the present invention has the following formula:

[0090]

[0091] wherein one of R 6 is hydroxyl and one of R 6 is a group of the following formula

[0092]

[0093] where F is as defined above and the dotted line is a bond to a carbon atom. The compound is preferably a mixture of the following two isomers:

[0094]

[0095]

[0096] wherein F is as defined above.

[0097] In a preferred embodiment, the compound used according to the present invention has the following formula:

[0098]

[0099] wherein x is from 1 to 10, preferably from 1 to 5, and F is as defined above.

[0100] In a preferred embodiment, R 3 is selected from a single bond and straight-chain, cyclic or branched, saturated, unsaturated or aromatic hydrocarbon groups having up to 18, preferably up to 12, more preferably up to 10 carbon atoms and optionally containing one or more groups selected from –O–, –NH–, –C(O)–, and wherein R 3 is optionally substituted by one or more groups selected from a hydroxyl group, an amino group, and a carboxyl group, preferably R 3 is a single bond or vinylene.

[0101] In a preferred embodiment of the present invention, R 2 is an aliphatic hydrocarbon group not derived from a sugar. A hexose is a monosaccharide having six carbon atoms with the chemical formula C6H 12 O6 and includes aldohexoses and their cyclic hemiacetals, as well as ketohexoses. In particular, they include glucose, and glucose is therefore preferably excluded.

[0102] In a further preferred embodiment of the present invention, R 2 is not derived from a carbohydrate (sugar), such as a monosaccharide, disaccharide, oligosaccharide, and polysaccharide, or a sugar alcohol. A carbohydrate or sugar is a biomolecule composed of carbon (C), hydrogen (H), and oxygen (O) atoms, typically having a hydrogen–oxygen atom ratio of 2:1 (as in water) and thus having the empirical formula C m (H2O) n (where m may be different from n). They also include deoxyribose, and structurally in particular include aldoses and ketoses, residues derived therefrom are therefore preferably excluded from R 2 A sugar alcohol (also called a polyhydric alcohol, polyol, alditol or glucitol) is an organic compound typically derived from a sugar, which includes a class of polyols and generally includes, for example, ethylene glycol, glycerol, erythritol, threitol, arabitol, xylitol, ribitol, mannitol, sorbitol, galactitol, fucitol, iditol, inositol, etc. (see, for example, https: / / en.wikipedia.org / wiki / Sugar_alcohol). In particular, R derived from ethylene glycol and glycerol is preferably excluded.2 .

[0103] In a further preferred embodiment of the present invention, R 2 is a carbohydrate- or sugar alcohol-ester not derived from gallic acid.

[0104] The present invention also relates to a compound of the following formula:

[0105] R 2 ”(–F) 2-18

[0106] wherein R 2 ” is an optionally substituted divalent to octadevalent aliphatic hydrocarbon group having up to 100 carbon atoms and optionally containing one or more groups selected from: –O–, –NH–, –C(O)–, –C(S)–, tertiary amino groups and quaternary ammonium groups and

[0107] F is selected from:

[0108] –O–C(O)–R 3 –R 4 , and

[0109] –NR 1 –C(O)–R 3 –R 4 .

[0110] The group F is attached to a carbon atom of R 2 ”, wherein R 2 ” is not derived from a carbohydrate (sugar) or sugar alcohol (for the definition of carbohydrate (sugar) or sugar alcohol, see the above explanation), and

[0111] wherein

[0112] R 1 is selected from hydrogen, or an optionally substituted straight-chain, cyclic or branched, saturated, unsaturated or aromatic hydrocarbon group having up to 100 carbon atoms and optionally containing one or more groups selected from: –O–, –NH–, –C(O)–, –C(S)–, tertiary amino groups and quaternary ammonium groups

[0113] R 3 is selected from a single bond or an optionally substituted straight-chain, cyclic or branched, saturated, unsaturated or aromatic hydrocarbon group having up to 100 carbon atoms and optionally containing one or more groups selected from: –O–, –NH–, –C(O)–, –C(S)–, tertiary amino groups and quaternary ammonium groups Preferably R3 is a single bond, or a vinylene group, and

[0114] R 4 is selected from di- and tri-hydroxy substituted aromatic groups.

[0115] These compounds according to the invention preferably exclude tannins as defined above.

[0116] The invention further relates to compounds of the formula:

[0117] R 2 ’(–F) 2-18

[0118] wherein R 2 ’ and F are each as defined above.

[0119] The invention further relates to compounds of the formula:

[0120]

[0121] wherein R 5 is selected from hydroxy or F, where F is as defined above, provided that at least two of R 5 are F.

[0122] The invention further relates to compounds of the formula:

[0123]

[0124] wherein one of R 6 is hydroxy and one of R 6 is a group of the formula

[0125]

[0126] where F is as defined above and the dashed line is a bond to a carbon atom.

[0127] The invention further relates to a mixture of the following two compounds:

[0128]

[0129] where F is as defined above.

[0130] Examples of precursors of compounds according to the invention containing a glycerol moiety are glycidyl-functional Denacol types EX-313, EX-314, EX-421, EX 512, EX 521 (Nagase).

[0131] Examples of precursors of the compounds according to the invention comprising trimethylolpropane, pentaerythritol and neopentyl glycol moieties are glycidyl-functional Denacol types EX-321, EX-411 and EX-211 (Nagase).

[0132] In another preferred embodiment of the invention, there is further involved a compound of the following formula:

[0133]

[0134] wherein x is from 1 to 10, preferably from 1 to 5, and F is as defined above.

[0135] Examples of precursors of the compounds according to the invention comprising propylene glycol moieties are glycidyl-functional Denacol types EX-920, EX-921 (Nagase).

[0136] Examples of precursors of the compounds according to the invention comprising ethylene glycol moieties are glycidyl-functional Denacol types EX-821, EX-830, EX-832, EX-841, EX-850, EX-851, EX-861 (Nagase).

[0137] Another embodiment of the invention relates to an aqueous composition which comprises at least one compound according to the invention as described above. In a preferred embodiment of the aqueous composition according to the invention, it optionally comprises at least one other component selected from: surfactants, and metal salts, preferably Zn 2+ 、Fe 2+ and / or Fe 3+ salts.

[0138] In a preferred embodiment of the aqueous composition according to the invention, the weight ratio of the optional surfactant and / or metal salt to the compound according to the invention is at least 0.06, more preferably 0.06 - 5, more preferably 0.06 - 3, even more preferably 0.1 - 3, especially 0.1 - 1.

[0139] The aqueous composition according to the invention preferably comprises 0.05 - 30%, more preferably 0.5 - 30%, more preferably 1 - 30%, even more preferably 1 - 20%, especially 1 - 10% of the compound of the invention, where each percentage is by weight based on the total weight of the aqueous composition.

[0140] The amount of surfactant present in the aqueous composition is preferably about 0.05% - about 15%, more preferably about 0.05% - about 5%, still more preferably about 0.1% - about 5%, especially 0.1 - 3% by weight of the aqueous composition.

[0141] Preferably, the surfactant is selected from: cationic, nonionic, betaine, and anionic surfactants, which preferably have an HLB value in the range of 1-20, preferably 7-20, more preferably 8-20. Preferred surfactants are selected from hydrocarbon-based or silicone-based emulsifiers.

[0142] The cationic surfactant is preferably selected from primary, secondary or tertiary amine compounds having up to 50 carbon atoms and their salts; amidoamine compounds having up to 50 carbon atoms and their salts, such as behenoyl aminopropyl dimethylamine; and quaternary ammonium compounds having up to 50 carbon atoms in their alkyl groups and preferably having up to 20 carbon atoms, such as tetraalkylammonium compounds such as cetyl-trimethylammonium salts, dimethyldioctadecylammonium salts, distearyldimethylammonium salts, cetyltrimethylammonium salts, cetylpyridinium salts, alkylbenzyldimethylammonium salts such as benzalkonium salts, phenethylammonium salts, and ester quaternary ammonium salts having at least one quaternary ammonium group and at least one ester group.

[0143] Further preferred examples of cationic emulsifiers are emulsifiers based on linear or branched C8-C50, preferably C8-40, more preferably C8-C30 alkyl fatty alcohols and fatty acids containing a quaternary ammonium group or an amino group, i.e., fatty acid-based ester quaternary ammonium salts containing one or two fatty acid moieties; fatty amines and ethoxylated / propoxylated fatty amines.

[0144] Preferably, the cationic surfactant is a mono-long alkyl–tri-short alkyl quaternary ammonium salt or a di-long alkyl–di-short alkyl quaternary ammonium salt, wherein one or two alkyl substituents are selected from aliphatic groups of about 8 to about 30 carbon atoms or aromatic, alkoxy, polyoxyalkylene, alkylamido, hydroxyalkyl, aryl or alkylaryl groups having up to about 30 carbon atoms; the other alkyl groups are independently selected from aliphatic groups of about 1 to about 8 carbon atoms or aromatic, alkoxy, polyoxyalkylene, alkylamido, hydroxyalkyl, aryl or alkylaryl groups having up to about 8 carbon atoms; and the counterion is a salt-forming anion such as those selected from: halogens (e.g., chloride, bromide), acetate, citrate, lactate, glycolate, phosphate, nitrate, sulfonate, sulfate, alkyl sulfate, glutamate, and alkyl sulfonate. The aliphatic groups may contain ether bonds and other groups such as amino groups in addition to carbon and hydrogen atoms. The longer chain aliphatic groups such as those having about 8 or more carbons may be saturated or unsaturated.

[0145] Preferably, one alkyl group is selected from alkyl groups having from about 8 to about 30 carbon atoms, more preferably from about 14 to about 26 carbon atoms, still more preferably from about 14 to 22 carbon atoms; the other alkyl groups are independently selected from -CH3, -C2H5, -C2H4OH, -CH2C6H5, and mixtures thereof; and the counterion is selected from Cl - , Br - , CH3OSO3 - , and mixtures thereof. It is believed that such mono-long alkyl quaternary ammonium salts can provide improved slipperiness on wet hair in addition to their emulsifying ability compared to multi-long alkyl quaternary ammonium salts. It is also believed that mono-long alkyl quaternary ammonium salts can provide improved hydrophobicity and smoothness on dry hair compared to amine or amine salt cationic surfactants.

[0146] Non-limiting examples of such mono-long alkyl quaternary ammonium salt cationic surfactants include: behenyl trimethyl ammonium chloride, which can be obtained, for example, from Clariant under the trade name Genamine KDMP, from Croda under the trade name INCROQUAT TMC-80, and from Sanyo Kasei as ECONOL TM22; stearyl trimethyl ammonium chloride, which can be obtained, for example, from Nikko Chemicals under the trade name CA-2450; cetyl trimethyl ammonium chloride, which can be obtained, for example, from Nikko Chemicals under the trade name CA-2350; behenyl trimethyl ammonium methyl sulfate, which can be obtained from FeiXiang; hydrogenated tallow alkyl trimethyl ammonium chloride; stearyl dimethyl benzyl ammonium chloride; and stearoyl-amidopropyl dimethyl benzyl ammonium chloride.

[0147] Preferred cationic surfactants are mono- and diester quaternary ammonium salts (quaternary ammonium salts = compounds comprising quaternary ammonium cations) based on saturated or unsaturated fatty acids having 10 - 18 carbon atoms in the alkyl chain. Commercially available examples are Arquad PC SV-60PG and Armocare VGH70 (Akzo Nobel).

[0148] Details regarding the cationic surfactant are disclosed in US2013 / 259820.

[0149] The aqueous composition of the present invention preferably comprises the cationic surfactant in an amount of from about 0.05% to about 15%, preferably from about 0.05% to about 5%, still more preferably from about 0.1% to about 5%, especially 0.1 - 3% by weight, alternatively 0% by weight, of the composition.

[0150] Preferred examples of nonionic emulsifiers are emulsifiers based on linear or branched C8-C50, preferably C8-40, more preferably C8-C24 fatty alcohols and fatty acids containing ethylene oxide (EO), propylene oxide (PO) and butylene oxide (BO), and sugar-based emulsifiers, namely alkyl glycosides, alkoxylated fatty acid sorbitan esters and fatty acid glucamides. Another class of preferred nonionic surfactants are semi-polar amine oxides, phosphine oxides, and sulfoxides.

[0151] Preferred nonionic surfactants are ethoxylates based on saturated or unsaturated natural alcohols having 10-18 carbon atoms in the alkyl chain and having 5-80 EO units. Commercially available examples are of the Genapol C, LA, V, O and T types (Clariant).

[0152] Preferred nonionic surfactants are ethoxylates based on linear or branched oxo alcohols having 11-17 carbon atoms in the alkyl chain and having 5-100 EO units. Commercially available examples are of the Genapol UD, OA, OX, X, LCN types (Clariant).

[0153] Preferred nonionic surfactants are block ethoxylate-propoxylates based on saturated or unsaturated alcohols having 10-18 carbon atoms in the alkyl chain and having 2-20 EO units. Commercially available examples are of the Genapol EP type (Clariant).

[0154] Preferred nonionic surfactants are ethoxylate-propoxylate block copolymers containing 5-70% by weight of EO units. Commercially available examples are of the Genapol PF and PH types (Clariant).

[0155] Preferred nonionic surfactants are ethoxylates based on saturated or unsaturated fatty acids having 10-18 carbon atoms in the alkyl chain and having 5-100 EO units. Commercially available examples are of the Genagen O and S types (Clariant).

[0156] Preferred nonionic surfactants are castor oil ethoxylates based on saturated or unsaturated fatty acids having 10-18 carbon atoms in the alkyl chain and having 5-80 EO units. Commercially available examples are of the Emulsogen HCO and EL types (Clariant).

[0157] Preferred nonionic surfactants are oligoglycerols derived from saturated or unsaturated fatty acids. Preferred examples are diglycerol, triglycerol, or tetraglycerol derived from fatty acids, i.e., mono- or diesters of diglycerol having 10-18 carbon atoms in the alkyl chain and optionally having 5-100 EO units. Commercially available examples are of the Hostacerine type (Clariant).

[0158] Preferred nonionic surfactants are ethoxylates of sorbitan esters of saturated or unsaturated fatty acids having 10-18 carbon atoms in the alkyl chain and having 5-50 EO units attached to the sorbitan ring. Commercially available examples are Emulsogen 4156 (Clariant).

[0159] Preferred nonionic surfactants are glycosides based on saturated or unsaturated alcohols having 8-18 carbon atoms in the alkyl chain and having 1-10 sugar units. Commercially available examples are Plantacare 818up and 1200up (BASF).

[0160] Preferred nonionic surfactants are glucamides based on saturated or unsaturated fatty acids having 8-18 carbon atoms in the alkyl chain, preferably fatty acid N-methylglucamides. Commercially available examples are of the MEGA-10 type (Avanti).

[0161] Preferred nonionic surfactants are alkanolamides based on saturated or unsaturated fatty acids having 8-18 carbon atoms in the alkyl chain, preferably ethanolamides based on fatty acids. Commercially available examples are of the Aminon C type (Kao).

[0162] Preferred nonionic surfactants are amine oxides based on fatty amines or fatty acid amides having 8-30 carbon atoms in the alkyl chain. Commercially available examples are of the Tomamine AO type (Air Products) and Genamineox type (Clariant).

[0163] The aqueous composition of the present invention preferably comprises the nonionic surfactant in an amount of about 0.05% - about 15%, preferably about 0.05% - about 5%, still more preferably about 0.1% - about 5%, particularly 0.1 - 3% by weight, alternatively 0% by weight, of the composition.

[0164] Preferred examples of betaine emulsifiers are emulsifiers based on linear or branched C8-C50, preferably C8-40, more preferably C8-C30 alkyl fatty alcohols and fatty acids containing carboxybetaine, sulfobetaine, phosphobetaine, and phosphonobetaine groups, i.e., cocamidopropyl carboxybetaine.

[0165] Preferably, suitable betaine surfactants for use in the compositions according to the invention include those known for use in shampoos or other personal care cleansers. They include those surfactants that are generically described as derivatives of aliphatic secondary and tertiary amines: where the aliphatic group can be straight or branched and where one of the aliphatic substituents contains from about 8 to about 30 carbon atoms and one contains an anionic group such as carboxyl, sulfonate, sulfate, phosphate, or phosphonate. Exemplary zwitterionic surfactants for use in the formulations of the present invention include cocoyl amphoacetate, cocoyl amphodiacetate, lauroyl amphoacetate, lauroyl amphodiacetate, and mixtures thereof. They also include those surfactants that are generically described as derivatives of aliphatic quaternary ammonium, phosphonium, and sulfonium compounds: where the aliphatic group can be straight or branched, and where one of the aliphatic substituents contains from about 8 to about 30 carbon atoms and one contains an anionic group such as carboxyl, sulfonate, sulfate, phosphate or phosphonate.

[0166] Preferred carboxybetaine surfactants are sarcosine metal salts based on saturated or unsaturated fatty acids having 10 - 18 carbon atoms in the alkyl chain. An example available commercially is Medialan LD (Clariant).

[0167] Preferred carboxybetaine surfactants are amido propyl betaines based on saturated or unsaturated fatty acids having 10 - 18 carbon atoms in the alkyl chain. An example available commercially is Genagen CAB (Clariant).

[0168] Preferred sulfobetaine surfactants are taurides based on saturated or unsaturated fatty acids having 10 - 18 carbon atoms in the alkyl chain. An example available commercially is Hostapon CT (Clariant).

[0169] Details regarding betaine surfactants are disclosed in US2015 / 011449.

[0170] The compositions of the present invention preferably include the betaine surfactant in an amount of from about 0.05% to about 15%, preferably from about 0.05% to about 5%, more preferably from about 0.1% to about 5%, especially 0.1 - 3% by weight, alternatively 0% by weight of the composition.

[0171] Preferred examples of anionic emulsifiers are emulsifiers based on linear or branched C8-C50, preferably C8-40, more preferably C8-C24 alkyl fatty alcohols and fatty acids containing carboxylate, sulfate, sulfonate, phosphate, and phosphonate groups, namely C8-C24 fatty acid carboxylates, C8-C24 fatty acid polyether carboxylates, C8-C24 fatty acid polyether sulfates, C8-C24 maleic acid adducts, C8-C24 fatty alcohol sulfates, C8-C24 sulfonates, C8-C40 phosphates containing one or two fatty acid moieties.

[0172] Preferably, the anionic surfactants suitable for use in the compositions are alkyl and alkyl ether sulfates. Other suitable anionic surfactants are water-soluble salts of organic, sulfuric acid reaction products. Still other suitable anionic surfactants are reaction products of fatty acids esterified with hydroxyethylsulfonic acid and neutralized with sodium hydroxide. Exemplary anionic surfactants for use in shampoo compositions include ammonium lauryl sulfate, ammonium polyethyleneglycol monolauryl ether sulfate, triethylamine lauryl sulfate, triethylamine polyethyleneglycol monolauryl ether sulfate, triethanolamine lauryl sulfate, triethanolamine polyethyleneglycol monolauryl ether sulfate, monoethanolamine lauryl sulfate, monoethanolamine polyethyleneglycol monolauryl ether sulfate, diethanolamine lauryl sulfate, diethanolamine polyethyleneglycol monolauryl ether sulfate, sodium monoglyceride lauryl sulfate, sodium lauryl sulfate, sodium polyethyleneglycol monolauryl ether sulfate, potassium lauryl sulfate, potassium polyethyleneglycol monolauryl ether sulfate, sodium lauroyl sarcosinate, sodium lauroyl sarcosinate, lauroyl sarcosine, cocoyl sarcosine, ammonium cocoyl sulfate, ammonium lauroyl sulfate, sodium cocoyl sulfate, sodium lauroyl sulfate, potassium cocoyl sulfate, potassium lauryl sulfate, triethanolamine lauryl sulfate, triethanolamine lauryl sulfate, monoethanolamine cocoyl sulfate, monoethanolamine lauryl sulfate, sodium tridecylbenzenesulfonate, sodium dodecylbenzenesulfonate, sodium cocoyl hydroxyethylsulfonate and combinations thereof. In a further embodiment of the invention, the anionic surfactant is sodium lauryl sulfate or sodium polyethyleneglycol monolauryl ether sulfate (sodium lauryl ether sulfate).

[0173] Preferred anionic surfactants are polyether sulfates based on saturated or unsaturated fatty alcohols having 10-18 carbon atoms in the alkyl chain and having 2-30 EO units. Commercially available examples are of the Emulsogen EPM type (Clariant).

[0174] Preferred anionic surfactants are polyether carboxylates based on saturated or unsaturated fatty alcohols having 10-18 carbon atoms in the alkyl chain and having 2-30 EO units. Commercially available examples are of the Empicol type (Huntsman).

[0175] Details regarding anionic surfactants are disclosed in US2015 / 011449.

[0176] Soaps in particular include salts of fatty acids such as alkali metal or alkaline earth metal salts of C6-C22 fatty acids such as sodium or potassium or calcium salts, such as those obtained by saponification of triglycerides, such as alkali metal or alkaline earth metal salts of lauric acid, myristic acid, palmitic acid, stearic acid, oleic acid, linoleic acid, linolenic acid.

[0177] The composition of the present invention preferably includes the anionic surfactant in an amount of about 0.05% - about 15%, preferably about 0.05% - about 5%, still more preferably about 0.1% - about 5%, especially 0.1 - 3% by weight, alternatively 0% by weight of the composition.

[0178] Further details regarding surfactants are disclosed in US 2009-0165812.

[0179] Preferred examples of silicone-based emulsifiers are cationic, nonionic, betaine, and anionic emulsifiers.

[0180] Preferred examples of cationic emulsifiers are: ABA-type emulsifiers containing quaternary ammonium groups (WO2009 / 042083) with the EO / PO moiety linked to the terminal quaternary ammonium (including quaternary ammonium cations) end of the silicone chain; or quaternized emulsifiers with the polyether moiety linked to the silicone chain in a comb-like arrangement (US2008 / 213208).

[0181] In another preferred embodiment of the present invention, a hydrophilic polyhydroxy moiety and a lipophilic fatty alkyl or fatty alkyl ester moiety are linked to the silicone chain (US2012 / 289649). Commercially available examples of this type of W / O emulsifier are EOF (available from Momentive Performance Materials).

[0182] The composition of the present invention preferably includes the silicone-based cationic surfactant in an amount of about 0.05% - about 15%, preferably about 0.05% - about 5%, still more preferably about 0.1% - about 5%, especially 0.1 - 3% by weight of the composition.

[0183] Preferred examples of the silicone-based nonionic emulsifiers are ABA-type emulsifiers in which ethylene oxide (EO), propylene oxide (PO) and butylene oxide (BO) are such that the EO / PO / BO moiety is linked to the end of the silicone chain, or emulsifiers in which the polyether moiety is linked to the silicone chain in a comb arrangement. Commercially available examples are SF 1540 (available from Momentive Performance Materials). In another preferred embodiment of the present invention, a hydrophilic polyether moiety and a lipophilic alkyl chain are linked to the silicone chain (US4698178). In another preferred embodiment of the present invention, a hydrophilic polyglycerol moiety and an alkyl or fatty alcohol ether / fatty acid ester moiety are linked to the silicone chain (US2010 / 0266651, US2009 / 0062459). In another preferred embodiment of the present invention, amino-terminated dimethicone glycerol carbamate is used (Dr. Frederic Pilz, COSSMA (2010) Volumes 7-8, page 18 and WO 2013017260 A1). In another preferred embodiment of the present invention, cetyl diglyceryl tris(trimethylsilyloxy)silylethyl dimethicone is used (http: / / ec.europa.eu / consumers / cosmetics / cosing / index.cfm?fuseaction=search.details_v2&id=92003).

[0184] For W / O emulsions, the latter four types of emulsifiers are particularly preferred.

[0185] The composition of the present invention preferably comprises the silicone-based nonionic surfactant in an amount of from about 0.05% to about 15%, preferably from about 0.05% to about 5%, more preferably from about 0.1% to about 5%, especially 0.1 - 3%, alternatively 0% by weight of the composition.

[0186] The composition of the present invention preferably comprises the silicone-based betaine and anionic surfactant in an amount of from about 0.05% to about 15%, preferably from about 0.05% to about 5%, more preferably from about 0.1% to about 5%, especially 0.1 - 3% by weight of the composition, alternatively 0% by weight.

[0187] The use of more than one surfactant to optimize formulation stability is within the scope of the present invention. The total amount of surfactant in the composition of the present invention preferably ranges from about 0.05% to about 15%, preferably from about 0.05% to about 5%, more preferably from about 0.1% to about 5%, especially 0.1 - 3% by weight of the composition, alternatively 0% by weight.

[0188] In a further embodiment of the present invention, the aqueous composition s optionally comprises additional additives, such as

[0189] a) an organic diluent or solvent,

[0190] b) a protein, preferably keratin,

[0191] c) a softening agent or fatty substance,

[0192] d) a preservative,

[0193] e) a skin protecting ingredient,

[0194] f) a conditioning agent,

[0195] g) an oxidizing agent,

[0196] h) a reducing agent,

[0197] i) tannin,

[0198] j) a metal salt,

[0199] k) other auxiliaries selected from: pH regulators, thickeners, lipids, amino acids, sugars, fragrances, sunscreens, vitamins, pearlescent agents, gelling agents, trace elements, masking agents, antioxidants, humectants, anti - hair loss agents, anti - dandruff agents, propellants, ceramides, polymers, especially film - forming polymers, fillers, nacre, colorants, especially pigments and dyes, and mixtures thereof,

[0200] provided that an oxidizing agent and a reducing agent are not present simultaneously in the given composition.

[0201] Preferably, the aqueous composition and the cosmetic composition of the present invention comprise the following components:

[0202]

[0203]

[0204] wherein the weight percentages relate to the total weight of the aqueous composition, and the individual weight ranges may relate to a single component of such a group of components, but preferably relate to the total weight of each component of such a group of components.

[0205] wherein the weight percentages relate to the total weight of the aqueous composition, and the individual weight ranges may relate to a single component of such a group of components, but preferably relate to the total weight of each component of such a group of components.

[0206] Diluent / solvent

[0207] The term "diluent / solvent" refers to a substance other than water that can be used to dilute / dissolve the at least one polyorganosiloxane A) according to the invention and / or the at least one organic compound B) and other optional additional components as previously mentioned. Suitable organic solvents are, for example, 2-methyl-1,3-propanediol, monoalcohols and diols or their ethers and esters, in particular mono C1-C3-alkyl ethers, ethanol, n-propanol, isopropanol, tert-butanol, 1-methoxypropanol, 1-ethoxypropanol and ethoxydiglycol, diols and their ethers and esters, 1,3-propanediol, 1,3- and 1,4-butanediol, pentanediol, hexanediol, diethylene glycol and its monomethyl and monoethyl ethers, dipropylene glycol and its monomethyl and monoethyl ethers, glycerol, diglycerol, hexanetriol, sorbitol, ethyl carbitol, benzyl alcohol, benzyloxyethanol, propylene carbonate, N-alkylpyrrolidone. In a preferred embodiment, water / ethanol, water / isopropanol, water / dipropylene glycol and water / propylene glycol monomethyl ether mixtures are used. Generally, the addition of a certain amount of short-chain alcohol improves the homogeneity of the formulation and the penetration of the formulation into the hair. Depending on the type of polymer structure and the application purpose, a certain amount of acid, base and / or short-chain alcohol is required to obtain a transparent formulation. Suitable acids include inorganic or organic acids, such as carboxylic acids like acetic acid, hydrochloric acid, sulfuric acid, phosphoric acid. Suitable bases include ammonia water, basic hydroxides, basic carbonates, etc.

[0208] Protein / keratin

[0209] The optional proteins used, preferably keratin protein fractions, include hydrolyzed keratin produced by alkaline and / or enzymatic hydrolysis using methods used in the art. The keratin hydrolyzate has a molecular weight of about 1,000 - 3,000. Keratin can be derived from human or other mammalian sources such as mountain goat hair (US 2007-0048235), hoof or horn powder (US 6,555,505). Alternatively, the "keratin protein fraction" is a purified form of keratin that mainly contains, although not completely, a unique proteome, as described in US 7,148,327. Details regarding keratin and keratin fractions are disclosed in US 2009-0165812.

[0210] Emollient, fatty substance

[0211] Other optional ingredients of the hair treatment formulation are one or more emollients. An "emollient" is a material that protects against moisture or irritation, softens, soothes, conditions, coats, lubricates, humidifies, protects and / or cleans the skin. The emollients used include one or more of the following: silicone compounds, namely dimethicone, cyclomethicone, preferably D5 and D6 cyclosiloxanes, dimethicone copolyol, or a mixture of cyclomethicone and dimethicone / vinyl dimethicone cross-linked polymer), polyols such as sorbitol, glycerin, propylene glycol, ethylene glycol, polyethylene glycol, caprylyl glycol, polypropylene glycol, 1,3-butanediol, hexylene glycol, isopentylene glycol, xylitol, ethylhexyl palmitate, triglycerides such as caprylic / capric triglyceride and fatty acid esters such as cetearyl isononanoate or cetyl palmitate. Details regarding emollients are disclosed in US 2009 / 0165812.

[0212] As fatty substances that are often referred to as oils and are liquid at ambient temperature and can be used in the present invention, mention may be made of: hydrocarbon-based oils of animal origin, such as perhydrosqualene; hydrocarbon-based vegetable oils, such as liquid triglycerides of fatty acids containing 4-10 carbon atoms, such as heptanoic or octanoic triglyceride, or sunflower oil, corn oil, soybean oil, grape seed oil, sesame oil, almond oil, macadamia nut oil, castor oil, avocado oil, caprylic / capric triglyceride, jojoba oil, shea butter; linear or branched hydrocarbons of mineral or synthetic origin, such as liquid paraffin and its derivatives, petrolatum, polydecene, hydrogenated polyisobutene such as Synthetic esters and ethers, especially synthetic esters and ethers of fatty acids, such as duck sebaceous gland oil, isopropyl myristate, 2-ethylhexyl palmitate, 2-octyldodecyl stearate, 2-octyldodecyl erucate, isostearyl isostearate, hydroxylated esters such as isostearyl lactate, octyl hydroxystearate, octyldodecyl hydroxystearate, diisostearyl malate, trisocetyl citrate, fatty alcohol heptanoates, octanoates and decanoates; polyol esters, such as propylene glycol dioctanoate, neopentyl glycol diheptanoate, diethylene glycol diisononanoate, pentaerythritol esters, fatty alcohols having 12-26 carbon atoms, such as octyldodecanol, 2-butyl octanol, 2-hexyldecanol, 2-undecylpentadecanol, oleyl alcohol, partially hydrocarbon-based and / or silicone-based fluorinated oils, silicone oils, such as linear or cyclic polydimethylsiloxanes (PDMS) that are liquid or pasty at ambient temperature (25 °C), such as cyclomethicone, dimethicone (optionally including phenyl groups), such as phenyltrimethicone, phenyltrimethylsilanoxy diphenylsiloxane, diphenylmethyl-dimethyltrisiloxane, diphenyldimethylsilicone, phenyldimethylsilicone, polymethylphenylsiloxane; mixtures thereof. Details regarding suitable fatty substances are disclosed in WO 2012-038334.

[0213] Preservative

[0214] Optionally, one or more preservatives may be included in the hair treatment formulation. Examples of such preservatives include one or more compounds containing glycerol (e.g., glycerol or ethylhexylglycerin or phenoxyethanol), lactic acid, benzyl alcohol, EDTA, potassium sorbate, and / or grape seed extract. In a preferred embodiment, the hair straightening formulation is free of parabens. Details regarding preservatives are disclosed in US 2009 / 0165812.

[0215] Skin protectant

[0216] Optionally, the hair treatment formulation includes one or more skin protectants. Skin protectants include one or more agents that prevent the unwanted penetration of microorganisms or organic / inorganic chemicals. Details regarding skin protectants are disclosed, for example, in US 2009 / 0165812.

[0217] Conditioner

[0218] Optionally, one or more conditioners may be included in the hair treatment formulation. In a preferred embodiment, silicone-based conditioners are introduced. Preferred materials are PDMS grades in the range of 10 - 1,000,000 mPa·s, silicones derivatized with C2 - C18 alkyl groups, polydimethylsiloxanol, polyether-modified silicones, silicones containing amino groups or quaternary ammonium groups. They may also be selected from polyorganosiloxanes having the functional group FA as defined above. These silicones may be introduced as pure materials, organic solutions, emulsions, or microemulsions.

[0219] Preferred examples of conditioning agents containing quaternary ammonium groups (quaternary ammonium salts) are silicone capped with α,ω - quaternary ammonium groups (US4891166), T - shaped silicone capped with quaternary ammonium groups (US2008027202), silicone block - capped with α,ω - silicone (WO02 / 10256), and silicone containing quaternary ammonium groups arranged in a comb - like manner, optionally containing additional moieties such as polyethers or aromatic structures (US2008213208, US5098979, US5153294, US5166297, US2006188456). Other preferred examples are copolymers based on quaternary ammonium group / silicone blocks (EP282720, US6240929, US6730766, DE102004002208). In another preferred embodiment, copolymers based on quaternary ammonium group / silicone block / hydrophilic block are used (WO 02 / 10257 and WO 02 / 10259, US7563856, US7563857, US20110039948, US2007106045, US2005255073, WO2004069137). Other preferred examples are copolymers based on quaternary ammonium group / silicone blocks and copolymers based on quaternary ammonium group / silicone block / hydrophilic block with terminal monofunctional silicone moieties (WO2013148629, WO2013148635, WO2013148935). In another preferred embodiment of the present invention, silicone capped with quaternary ammonium groups with pendant amino groups is used (DE10253152). Other preferred examples are silicone betaines (DE10036522, DE10036532). Commercially available examples of siloxanes containing quaternary ammonium groups are Silsoft Silk and Silsoft Q (available from Momentive Performance Materials).

[0220] The above - mentioned silicone - based conditioning agents particularly impart smoothness and a satin - like feel to the hair.

[0221] Alternatively, hydrocarbon - based conditioning agents may be included. Details regarding these cationic materials containing amino and / or quaternary ammonium groups are disclosed, for example, in US 2009 / 0000638 and WO 2012 / 027369.

[0222] Oxidizing agent

[0223] Optionally, one or more oxidizing agents may be included in the hair treatment formulation. Preferred oxidizing agents include organic oxidizing agents, namely benzoquinone, other quinone derivatives, including hydroquinone and aminoquinone, and suitable organic peroxides. Details regarding organic oxidizing agents are disclosed in US 2012 / 0031420 and WO 2012 / 027369.

[0224] Hydrogen peroxide is the preferred inorganic oxidizing agent. Persulfates (in the form of their sodium, potassium, and ammonium salts) can also be used, either alone or in combination with hydrogen peroxide just before use. Other possible oxidizing agents include sodium percarbonate, sodium perborate, magnesium perborate, magnesium dioxide, and barium dioxide. Details regarding these oxidizing agents are disclosed in US 6544499.

[0225] Reducing agent

[0226] Optionally, one or more reducing agents may be included in the hair treatment formulation, provided that an oxidizing agent and a reducing agent are not present simultaneously in the given formulation. Preferred reducing agents are thioglycolic acid and thiolactic acid and their salts, especially ammonium and ethanolamine salts. Other useful sulfur-containing compounds are cysteine or its hydrochloride, homocysteine, cysteamine, N-acetylcysteine, thioglycerol, ethylene glycol monothioglycolate, 1,2-propylene glycol monothioglycolate (see also WO 93 / 1791), 1,3-propylene glycol monothioglycolate or an isomer mixture obtained therefrom, 1,3-butanediol and 1,4-butanediol monothioglycolate and an isomer mixture obtained therefrom, polyethylene glycols such as diethylene glycol, triethylene glycol, and tetraethylene glycol monothioglycolates, glycerol monothiolactate and other thioacids and their esters, and mixtures thereof. Details regarding these organic reducing agents are disclosed in US 2009 / 0000638.

[0227] The use of inorganic reducing sulfur compounds is also basically possible. Representative examples for use in such reducing compositions include cosmetically acceptable salts (e.g., alkali metals (e.g., sodium and potassium) and ammonium salts), esters (e.g., lower alkyl), amines (e.g., triethanolamine (TEA), monoethanolamine (MEA), and aminomethylpropanol (AMP)), sulfites, disulfites, bisulfites, metabisulfites, hyposulfites, dithionites, and pyrosulfites). Specific examples of suitable reducing agents thus include sodium metabisulfite, potassium metabisulfite, sodium sulfite, potassium sulfite, sodium thiosulfate, potassium thiosulfate, ammonium bisulfite, ammonium sulfite, ammonium metabisulfite, MEA sulfite, MEA metabisulfite, potassium bisulfite, sodium bisulfite, ammonium bisulfite, sodium hyposulfite, potassium hyposulfite, ammonium hyposulfite, anhydrous sodium sulfite, diammonium sulfite, dipotassium disulfite, dipotassium pyrosulfite, AMP sulfite, AMP metabisulfite, TEA sulfite, TEA metabisulfite, sodium acid sulfite, sodium dithionite, sodium pyrosulfite, and sodium thiosulfate pentahydrate. Details regarding these inorganic reducing agents are disclosed in WO 2012 / 027369.

[0228] Alternatively, keratin treated with high temperature and alkali (wherein the keratin is heated to about 100 °C or higher), dithionite, and certain hydrides can be used. Details regarding these reducing agents are disclosed in US 6544499.

[0229] K) Tannin

[0230] Optionally, one or more tannins can be used, in particular gallotannins, ellagitannins, complex tannins, condensed tannins, namely tannic acid and its other forms quercitannic acid and gallocatechinic acid. Tannins represent a class of polyphenol derivatives and are well-known for their structural diversity. The classification is based on that given by K. Khanbabaee, T. van Ree, Nat. Prod. Rep., 2001, 18, 641 - 649 (which is included as a reference herewith) and is used to define the term tannin in the context of the present invention. The most preferred tannin is gallocatechinic acid ( = tannic acid). Preferred tannins include:

[0231]

[0232] Examples of gallotannins are

[0233]

[0234] Examples of ellagitannins are

[0235]

[0236] An example of a complex tannin is Acutissimin A

[0237]

[0238] Examples of condensed tannins are procyanidin B2 (77), proanthocyanidin A1 (78), proanthocyanidin A2 (79), and proanthocyanidin C1 (80):

[0239]

[0240] The most preferred tannin is tannic acid:

[0241]

[0242] Metal salt

[0243] including in particular those of the following general formula:

[0244] Me x A y

[0245] In this formula, Me is a metal cation, the number of cations Me is x, and the number of anions A is y, and the numbers x and y are such that the salt is neutral. In particular, x can be, for example, 1 or 2, and y can be, for example, 1 - 3. A is preferably an anion of an oxidized carbohydrate of the formula - O-C(O)-R, or an anion derived from an inorganic or organic acid. Me is preferably an iron or zinc cation.

[0246] Particularly preferred salts are Fe or Zn salts, which are preferably water-soluble, such as Fe lactobionate 2+ , Fe maltobionate 2+ , Fe isomaltobionate 2+ , Fe lactobionate 3+ , Fe maltobionate 3+ , Fe isomaltobionate 3+ , Fe gluconate 2+ , Fe gluconate 3+ , Fe glucoheptonate 2+ , Fe glucoheptonate 3+ , Fe glycerophosphate 2+ , Fe glycerophosphate 3+ , Zn lactobionate 2+ , Zn maltobionate 2+ , Zn isomaltobionate 2+ , Zn gluconate 2+ , and Zn glycerophosphate 2+ , Fe tartrate 2+ , Fe glucaric acid 2+ , Fe tartrate 3+ , Fe glucaric acid 3+ , Zn tartrate 2+ , Zn glucaric acid 2+ .

[0247] The weight ratio of the Fe or Zn salt to the compound according to the invention containing an aromatic group substituted with two or three hydroxyl groups is at least 0.01, preferably 0.01 - 3, more preferably 0.02 - 3, even more preferably 0.05 - 3, particularly 0.1 - 3, and even more particularly 0.1 - 1. If the optional tannin is additionally used, the weight ratio of the water-soluble Fe or Zn salt to the compound + tannin according to the invention containing an aromatic group substituted with two or three hydroxyl groups is at least 0.01, preferably 0.01 - 3, more preferably 0.02 - 3, even more preferably 0.05 - 3, particularly 0.1 - 3, and even more particularly 0.1 - 1. If the optional tannin is used, the weight ratio of the tannin to the organic compound according to the invention containing an aromatic group substituted with two or three hydroxyl groups is 0.01 - 5, preferably 0.01 - 3, more preferably 0.02 - 3, even more preferably 0.05 - 3, particularly 0.1 - 3, and even more particularly 0.1 - 1.

[0248] The specific amount of the water-soluble Fe or Zn salt depends on the molecular weight and structure of the water-soluble Fe or Zn salt and the molar ratio of the di- or tri-hydroxy-substituted aromatic group in the compound of the present invention and the optionally used tannin. Typically, the higher the molecular weight of the water-soluble Fe or Zn salt and / or the higher the molar ratio of the di- or tri-hydroxy-substituted aromatic group in the compound of the present invention and the optional tannin, the higher the specific amount of the water-soluble Fe or Zn salt used.

[0249] Other adjuvants

[0250] The hair treatment formulation may further comprise one or more additional adjuvants, namely pH regulators such as acids, bases and buffers for adjusting the pH value, thickeners (such as polysaccharide thickeners, starches, modified starches, xanthan gum, exopolysaccharides, carrageenan, pullulan, cellulose, cellulose derivatives, polyacrylic acid, polyacrylate copolymers, polyacrylamide, pectin, clay, pyrogenic silica), lipids, amino acids, sugars, fragrances, sunscreens, vitamins, pearlescent agents, gelling agents, trace elements, masking agents, antioxidants, humectants, anti-hair loss agents, anti-dandruff agents, propellants, ceramides, polymers, especially film-forming polymers; fillers, nacre, colorants and especially pigments and dyes, including hair dyes as described below, all kinds of bioactive phytochemicals, and mixtures thereof.

[0251] Hair dye

[0252] Including common oxidative or non-oxidative, temporary, semi-permanent, quasi-permanent and permanent hair dyes. Temporary non-oxidative dyes include, for example, Acid Yellow, Acid Orange 7, Acid Yellow 1, Acid Red 33, Acid Red 92, Acid Violet 43, Acid Blue 9, Acid Black 1, which are often used in mixtures. Semi-permanent non-oxidative hair dyes contain basic or cationic dyes with low molar mass and especially include HC Yellow No. 2, HC Red No. 3, 4-hydroxypropylamino-3-nitrophenol, N,N'-bis-(2-hydroxyethyl)-2-nitrophenylenediamine, HC Blue No. 2, Basic Red 51, Basic Red 76, Basic Brown 16, Basic Brown 17, Basic Blue 99, Basic Yellow 57. Other semi-permanent dyes include metal derivatives and plant derivatives (such as henna). The metal dyes are derived from silver salts, lead, and bismuth. Permanent oxidative hair dyes include common complex systems of precursors in the presence of an oxidizing agent.

[0253] Depending on the type of polymer structure and the purpose of application, a certain amount of acid, base, and / or short-chain alcohol is required to obtain a clear formulation. Suitable acids include inorganic or organic acids, such as carboxylic acids like acetic acid, hydrochloric acid, sulfuric acid, and phosphoric acid. Suitable bases include ammonia water, basic hydroxides, basic carbonates, etc.

[0254] By adding an acid or base such as this, the suitable pH range of the aqueous composition can be adjusted, for example, to below 9, preferably below 8.5, preferably below 7.5, and more preferably below 7.0.

[0255] A further preferred embodiment of the present invention relates to a cosmetic composition or personal care formulation, which comprises at least one compound according to the present invention as defined herein, or at least one aqueous composition according to the present invention.

[0256] Examples of personal care or cosmetic compositions in which the compounds of the present invention can be used include, but are not limited to, for example, deodorants, antiperspirants, antiperspirant / deodorants (including spray, stick, and roll-on products), shaving products, body lotions, moisturizing creams, toners, bath products, cleansing products, shampoos, conditioners, combined shampoo / conditioners, mousses, styling gels, hairsprays, hair dyes, hair color products, hair bleaches, hair perming products, hair straighteners, nail polishes, nail polish removers, nail creams and lotions, cuticle softeners, sunscreens, insect repellents, anti-aging products, lipsticks, foundations, face powders, eyeliners, eyeshadows, blushes, makeup, mascaras, moisturizing preparations, foundations, body and hand preparations, skin care preparations (skin care formulations), facial and neck preparations, tonics, dressings, hair grooming aids, aerosol styling agents, fragrance preparations, aftershaves, makeup preparations, soft focus applicators, day and night skin care preparations, non-coloring hair preparations, tanning preparations, synthetic and non-synthetic soap bars, hand sanitizers, nose strips, non-woven applicators for personal care, baby body lotions, baby bath products and shampoos, baby conditioners, shaving preparations, cucumber slices, skin pads, makeup removers, facial cleansing products, cold creams, sun protection products, mousses, injections, cream masks and mud masks, face masks, colognes and eaux de toilette, hair cuticle coatings, shower gels, facial and body washes, personal care rinse-off products, gels, bubble baths, scrubbing cleansers, astringents, nail conditioners, eyeshadow sticks, face or eye powders, lip balms, lip glosses, hair pump sprays and other non-aerosol sprays, hair frizz control gels, leave-in hair conditioners, hair oils, hair detangling products, hair styling agents, hair bleaching products, body lotions, shaving creams and electric shaving creams, anhydrous creams and lotions, oil-in-water, water-in-oil, multiple and coarse and microemulsions, waterproof creams and lotions, anti-acne preparations, mouthwashes, massage oils, toothpastes, cleansing gels and sticks, ointment bases, topical wound healing products, aerosol talc, barrier sprays, vitamin and anti-aging preparations, herbal extract preparations, bath salts, bath and body milks, hair styling aids, hair-, eye-, nail-, and skin-soft solid applicators, controlled release personal care products, hair conditioning sprays, skin care moisturizing sprays, skin wipes, pore skin wipes, pore cleansers, acne reducers, skin exfoliants, skin desquamation enhancers, skin washcloths and cloths, depilatory preparations, personal care lubricants, nail coloring preparations, sunscreens, cosmetics, hair care products, skin care products, toothpastes, drug delivery systems for external administration of medical compositions to be applied to the skin, combinations of two or more thereof, etc. Such cosmetic or personal care compositions of the present invention can include other ingredients and components as desired for a specific purpose or intended use.For example, a personal care composition may include ingredients selected from the following: emollients, moisturizing creams, humectants, pigments, coated mica, colorants, fragrances, biocides, preservatives, antioxidants, antimicrobials, antifungals, antiperspirants, exfoliants, hormones, enzymes, medical compounds, vitamins, salts, electrolytes, alcohols, polyols, ultraviolet radiation absorbers, plant extracts, surfactants, silicone oils, organic oils, waxes, film formers, thickeners, particulate fillers, clays, surfactants, emulsifiers, solvents, emollients, moisturizing creams, humectants, pigments, colorants, fragrances, biocides, preservatives, chelating agents, antioxidants, antimicrobials, antifungals, antiperspirants, exfoliants, hormones, enzymes, medical compounds, vitamins, alpha-hydroxy acids, beta-hydroxy acids, retinol, niacinamide, skin brighteners, salts, electrolytes, alcohols, polyols, ultraviolet radiation absorbers, plant extracts, organic oils, waxes, film formers, thickeners, particulate fillers, silicones, clays, plasticizers, humectants, occlusives, sensory enhancers, esters, resins, film formers, film-forming emulsifiers, high refractive index materials, combinations of two or more thereof, and the like.

[0257] Cosmetic products can be applied to the face, such as skin care creams (skin creams), lipsticks, eye and face makeup, wipes, and colored contact lenses. Cosmetic products can be applied to the body, such as deodorants, lotions, powders, perfumes, baby products, bath oils, bubble baths, bath salts, and body butters; can be applied to the hands / nails: fingernail and toenail polishes, and hand sanitizers; can be applied to the hair: permanent chemicals, hair colors, hairsprays, and gels; makeup compositions including color pigments, cosmetic products can be particularly applied to the face and eye areas, such as primers, foundations or eyeshadows, lipsticks, lip glosses, lip liners, plumping lip glosses, lip balms, lip stains, lip primers, lip mists, and lip butters, which may contain sunscreen, concealers, face powders, mascaras, eyeshadows, eyeliners, eyebrow pencils, creams, waxes, gels, and powders (for coloring, delineating, and defining eyebrows); lotions, cleansing formulations; toners; masks; peel-off masks, sheet masks, exfoliant products, moisturizers such as creams or lotions, which may contain essential oils, herbal extracts, or other chemicals; night creams, day creams, sunscreen compositions, nail polishes, and the like.

[0258] Personal care products that may include the compounds of the present invention include, for example, cosmetic and medical products, such as bar soaps, liquid soaps (such as hand soaps), hand sanitizers (including rinse-off and alcohol-based and water-based hand disinfectants that do not require rinsing), skin disinfectants before surgery, cleansing wipes, disinfecting wipes, shower gels, acne treatment products, skin creams, shampoos, conditioners, cosmetics (including but not limited to liquid or powder foundations, liquid or solid eyeliners, mascaras, cream eyeshadows, colored face powders, "pancake" type face powders for use in dry or wet conditions, etc.), deodorants, antimicrobial creams, body lotions (lotions), hand creams, topical creams, aftershave lotions (lotions), toners, mouthwashes, toothpastes, sunscreen lotions; and baby products, such as, but not limited to, cleansing wipes, baby shampoos, baby soaps, and diaper rash creams; wound care items, such as, but not limited to, wound healing ointments, creams, and lotions (lotions), wound dressings, burn wound creams, bandages, tapes, and surgical skin closures; and medical products such as medical gowns, caps, masks, and shoe covers, surgical drapes, etc. Additional products include but are not limited to oral products such as oral rinses, toothpastes, and dental floss coatings, veterinary and pet care products, preservative compositions, and surface disinfectants, including solutions, sprays, or wipes, etc.

[0259] The aqueous or cosmetic composition according to the present invention can be specifically formulated (for or as) in the forms typical of hair treatment compositions. Preferred are topical hair care or treatment compositions, such as hair tonics, conditioners (hair conditioners), hair care preparations, such as pretreatment preparations, styling creams, styling gels, hair oils, shampoos, treatment packs, intensive hair treatment agents such as leave-in and rinse-off deep conditioners (hair conditioners), preparations for hair structuring, such as perming preparations (hot perm, warm perm, cold perm) for permanent waving, hair straightening preparations, liquid hair styling preparations, hair foams, hair serums, hairsprays, bleaching preparations, such as hydrogen peroxide solutions, brightening shampoos, bleaching creams, bleaching powders, bleaching pastes or oils, temporary, semi-permanent or permanent hair colorants, preparations containing self-oxidizing dyes, or natural hair colorants such as henna or chamomile. Depending on the application, the hair care preparations can be specifically in the form of: (aerosol) sprays, (aerosol) foams, gels, gel sprays, creams, lotions (lotions), liquids, serums or waxes, mousses, shampoos, such as pearl shampoos, anti-frizz shampoos, etc. The aqueous composition according to the present invention can be used as a leave-in or rinse-off hair treatment composition.

[0260] A particularly preferred cosmetic composition according to the invention is used in hair treatment, preferably in hair coloring treatment. The above-mentioned aqueous cosmetic composition according to the invention can particularly provide benefits in terms of improved durability of artificial color on the hair. In addition, the aqueous hair treatment formulation according to the invention provides hair strengthening and shaping effects as well as conditioning effects, especially before, during and after hair coloring treatments such as hair bleaching treatments. The hair treatment composition according to the invention can provide benefits in terms of hair strengthening, hair coloring, color retention of the hair and shaping, i.e., curling and straightening of the hair.

[0261] The preferred cosmetic compositions for treating hair according to the invention are selected from hair shampoo compositions, hair care compositions, hair conditioning compositions, hair strengthening compositions, hair coloring or dyeing compositions, hair combability improving compositions, anti-frizz compositions, hair rinse-off and leave-on compositions.

[0262] In a further embodiment, the invention relates to a method for treating hair, which comprises the steps of: providing a cosmetic composition according to the invention, and applying the cosmetic composition to the hair. Such a method for treating hair may further comprise the step of dyeing the hair.

[0263] A specific preferred method for treating hair involves the following steps:

[0264] 1) bringing the hair into contact with the aqueous cosmetic composition of the invention,

[0265] 2) optionally bringing the hair into contact with an aqueous composition comprising a metal salt of Fe and / or Zn, comprising an aqueous phase, having a pH in the range from >2 to 10, and comprising water-soluble Zn 2 + 、Fe 2+ and / or Fe 3+ salts:

[0266] chloride, sulfate, alkylsulfonate, arylsulfonate, alkylarylsulfonate,

[0267] hydroxy-functionalized carboxylic acids, said hydroxy-functionalized carboxylic acids being especially selected from

[0268] C2-C12, preferably C2-C9 saturated or unsaturated hydroxyalkyl carboxylic acids, namely glycolic acid, lactic acid, β-hydroxybutyric acid, γ-hydroxybutyric acid, 2-hydroxy-succinic acid, citric acid, mandelic acid,

[0269] C2-C12, preferably C2-C9, more preferably C7-C12, even more preferably C7-C9 saturated or unsaturated polyhydroxyalkyl carboxylic acids, namely glycolic acid, 2,2-dimethylolpropionic acid, arabinonic acid, gluconic acid, glucuronic acid, glucoheptonic acid, glucopyranosyl arabinonic acid, lactic acid, maltonic acid, tartaric acid, glucaric acid,

[0270] C7-C12, preferably C7-C9 hydroxyaromatic carboxylic acids, namely 2-hydroxybenzoic acid, 3-hydroxybenzoic acid, 4-hydroxybenzoic acid, 2-hydroxycinnamic acid, 3-hydroxycinnamic acid, 4-hydroxycinnamic acid,

[0271] C7-C12, preferably C7-C9 polyhydroxyaromatic carboxylic acids, namely 2,3-dihydroxybenzoic acid, 2,4-dihydroxybenzoic acid, 2,5-dihydroxybenzoic acid, 2,6-dihydroxybenzoic acid, 3,4-dihydroxybenzoic acid, 3,5-dihydroxybenzoic acid, dihydroxycinnamic acid or its partial ester namely 3,4-dihydroxycinnamic acid, trihydroxybenzoic acid or its partial ester namely 2,3,4-trihydroxybenzoic acid, 2,3,5-trihydroxybenzoic acid, 2,3,6-trihydroxybenzoic acid, 2,4,5-trihydroxybenzoic acid, 2,4,6-trihydroxybenzoic acid, 3,4,5-trihydroxybenzoic acid, trihydroxycinnamic acid or its partial ester namely 3,4,5-dihydroxycinnamic acid, and mixtures thereof, and

[0272] 3) Dry the hair at a temperature preferably > 150 °C, for example during a hot ironing step, which mainly binds or introduces the hair treatment composition of the present invention used in steps 1) and 2) or a part of the hair treatment composition to the hair.

[0273] Another specific preferred method for treating hair involves the following steps:

[0274] 1) Contact the hair with the aqueous cosmetic composition of the present invention, which composition comprises a compound of the present invention, optionally one or more surfactants as described above, and a metal salt of Fe and / or Zn, which metal salt is preferably a water-soluble Zn 2+ , Fe 2+ and / or Fe 3+ salt:

[0275] chloride, sulfate, alkylsulfonate, arylsulfonate, alkylarylsulfonate,

[0276] hydroxy-functionalized carboxylic acids, which hydroxy-functionalized carboxylic acids are particularly selected from

[0277] C2-C12, preferably C2-C9 saturated or unsaturated hydroxyalkyl carboxylic acids, namely glycolic acid, lactic acid, β-hydroxybutyric acid, γ-hydroxybutyric acid, 2-hydroxy-succinic acid, citric acid, mandelic acid,

[0278] C2-C12, preferably C2-C9, more preferably C7-C12, even more preferably C7-C9 saturated or unsaturated polyhydroxyalkyl carboxylic acids, namely glyceric acid, 2,2-dimethylolpropionic acid, arabinonic acid, gluconic acid, glucuronic acid, glucoheptonic acid, glucopyranosyl arabinonic acid, lactic acid, maltobionic acid, tartaric acid, mucic acid

[0279] C7-C12, preferably C7-C9 hydroxyaromatic carboxylic acids, namely 2-hydroxybenzoic acid, 3-hydroxybenzoic acid, 4-hydroxybenzoic acid, 2-hydroxycinnamic acid, 3-hydroxycinnamic acid, 4-hydroxycinnamic acid,

[0280] C7-C12, preferably C7-C9 polyhydroxyaromatic carboxylic acids, namely 2,3-dihydroxybenzoic acid, 2,4-dihydroxybenzoic acid, 2,5-dihydroxybenzoic acid, 2,6-dihydroxybenzoic acid, 3,4-dihydroxybenzoic acid, 3,5-dihydroxybenzoic acid, dihydroxycinnamic acid or its partial ester, namely 3,4-dihydroxycinnamic acid, trihydroxybenzoic acid or its partial ester, namely 2,3,4-trihydroxybenzoic acid, 2,3,5-trihydroxybenzoic acid, 2,3,6-trihydroxybenzoic acid, 2,4,5-trihydroxybenzoic acid, 2,4,6-trihydroxybenzoic acid, 3,4,5-trihydroxybenzoic acid, trihydroxycinnamic acid or its partial ester, namely 3,4,5-dihydroxycinnamic acid, and mixtures thereof, and

[0281] 2) drying the hair at >150 °C, for example during hot ironing, which mainly binds or introduces the hair treatment composition of the present invention used in step 1) or a part of the hair treatment composition to the hair or into the hair.

[0282] In the above method, the weight ratio of the optional water-soluble Fe and / or Zn salt to the compound containing a di- or tri-hydroxy-substituted aromatic group according to the present invention is at least 0.01, preferably 0.01-3, more preferably 0.02-3, even more preferably 0.05-3, especially 0.1-3, and even more particularly 0.1-1. If the optional tannin is used, the weight ratio of the water-soluble Fe and / or Zn salt to the organic compound + tannin containing a di- or tri-hydroxy-substituted aromatic group is at least 0.01, preferably 0.01-3, more preferably 0.02-3, even more preferably 0.05-3, especially 0.1-3, and even more particularly 0.1-1. The specific amount of the water-soluble Fe and / or Zn salt depends on the molecular weight and structure of the water-soluble Fe or Zn salt and the molar ratio of the di- or tri-hydroxy-substituted aromatic group in the compound of the present invention and the optionally used tannin. Typically, the higher the molecular weight of the water-soluble Fe or Zn salt and / or the higher the molar ratio of the di- or tri-hydroxy-substituted aromatic group in the organic compound of the present invention and the optional tannin, the higher the specific amount of the water-soluble Fe or Zn salt used.

[0283] Preferably, the method step 1) of contacting hair with a hair treatment composition based on a compound containing a di- or tri-hydroxy-substituted aromatic group and an optional surfactant to form treated hair is carried out at a temperature and for a duration sufficient to penetrate the fibers. Typically, method step 1) is carried out at 10 - 50 °C, preferably 20 - 50 °C, even more preferably at room temperature for 5 - 20 min, preferably 5 - 60 min, even more preferably 10 - 40 min.

[0284] Preferably, the method step 2) of contacting hair with the hair treatment composition of the present invention based on water-soluble Zn 2+ , Fe 2+ and / or Fe 3+ salts to form further treated hair is carried out at a temperature and for a duration sufficient to penetrate the fibers. Typically, method step 2) is carried out at 10 - 50 °C, preferably at 20 - 50 °C, even more preferably at room temperature for 5 - 120 min, preferably 5 - 60 min, even more preferably 10 - 40 min.

[0285] Preferably, the method step 3) of drying the treated hair at a temperature > 150 °C by applying heat is preferably a hot ironing step, which mainly binds or introduces the hair treatment composition of the present invention used in steps 1) and 2) or a part of the hair treatment composition to the hair. This elevated temperature can cause a chemical reaction between the components of the composition used in steps 1) and 2) and the reactive parts of the keratin fibers, or the formation of a complex of the components of the composition used in steps 1) and 2). The preferred temperature range is 150 °C - about 235 °C, more preferably 180 °C - about 225 °C, even more preferably 190 °C - about 215 °C. Typically, 2 - 10 rounds of hot ironing are applied when drying the hair.

[0286] In the context of the present invention, the water-soluble Zn and / or Fe salts used in step 2) preferably have a water solubility of at least 0.5 g / l at 25 °C.

[0287] The above hair treatment method according to the present invention can provide benefits in terms of hair strengthening, hair shaping i.e. curling and straightening of hair, hair coloring, hair bleaching, hair color retention, and hair conditioning.

[0288] The present invention further relates to the use of the aqueous composition according to the present invention for treating hair, in particular for hair strengthening, for hair color retention, for hair color enhancement, for hair color deepening, for hair color protection, for hair shaping i.e. curling and straightening of hair, for hair conditioning, for hair smoothing or softening, for hair straightening, for improving the manageability of hair, in particular for improving the combability of hair.

[0289] Aspects of the present invention can be further understood with reference to the following non-limiting examples. Examples

[0290] Example 1

[0291] Synthesis of gallic acid derivatives based on diglycidyl ether of glycerol

[0292] 54.1 g of 1,3-butanediol, 15 g (0.088 mol –COOH) of gallic acid and 0.46 g of trimethylamine were mixed at room temperature and heated to 70 °C. 8.18 g (0.080 mol epoxy groups) of diglycidyl ether of glycerol was added dropwise over a period of 30 minutes. The mixture was heated to 90 °C for 12 hours. The conversion rate of epoxy groups was 100% (1H-NMR).

[0293] A slightly yellowish transparent liquid containing a product consisting essentially of the following structure was obtained:

[0294]

[0295] wherein

[0296]

[0297] and R2 is –OH or in a ratio of 1:1

[0298]

[0299] Example 2

[0300] Synthesis of gallic acid derivatives based on propylene glycol

[0301] 56.86 g of 1,3-butanediol, 8.95 g (0.0526 mol –COOH) of gallic acid and 0.28 g of trimethylamine were mixed at room temperature and heated to 70 °C. 10 g (0.0526 mol epoxy groups) of the structure of glycidyl-modified oligo-propylene glycol derivative was added dropwise over a period of 1 h. The mixture was heated to 90 °C for 14 hours. The conversion rate of epoxy groups was 100% (1H-NMR).

[0302] A yellowish transparent liquid containing a product consisting essentially of the following structure was obtained:

[0303]

[0304] wherein

[0305]

[0306] Application

[0307] Measurement method:

[0308] Test method for measuring the color and color retention of hair dyes

[0309] The test method for evaluating color retention is described in detail in US 2011 / 0219552 A1. This method determines the change in hair color (ΔE) before and after washing the hair. This color change is determined by measuring the Hunter L, a, and b values on a HunterLab colorimeter before and after washing a tress of color-treated hair.

[0310] The meaning of L, a, and b is described in detail in "Practical Modern Hair Science" by Trefor Evans and R. Randall Wichett, Alluredbooks, Carol Stream, Illinois, 2012. The L value measures the lightness from L = 0 (black) to L = 100 (white). Color is measured by a from negative values (green) to positive values (red) and b from negative values (blue) to positive values (yellow). For example, medium ash blonde has L, a, b values of L = 49, a = 12, b = 26 and medium auburn has L, a, b values of L = 26, a = 13, b = 12.

[0311] The following equation is used to calculate ΔE to evaluate the color change before and after washing.

[0312] ΔE w = ((L t - L0) 2 +(a t - a0) 2 +(b t - b0) 2 ) 1 / 2

[0313] where L0, a0, b0 (initial color parameters) and L t , a t , b t (color parameters after washing) are the measured Hunter L, a, b color parameters. The larger the value of ΔE, the greater the color change, so a smaller ΔE is desired as it indicates less color loss after washing.

[0314] Similarly, the following equation is used to calculate color enhancement to evaluate the increase in initial color depth with treatment.

[0315] ΔE e = ((L2 - L1)2 +(a2 - a1) 2 +(b2 - b1) 2 ) 1 / 2

[0316] Wherein L2, a2, b2 (color parameters of the treated and colored hair) and L1, a1, b1 (color parameters of the untreated and colored hair) are measured without washing. Here, a larger ΔE is desired as it means a greater initial color enhancement.

[0317] Example 3: Cream shampoo

[0318]

[0319]

[0320] Procedure:

[0321] 1. Prepare Phase A in the main container: Dissolve disodium EDTA in deionized water, add Carbopol Aqua SF-1 polymer and mix gently, add Galaxy LES and mix gently.

[0322] 2. Neutralize Phase A with Phase B to pH 6.6 - 7.2

[0323] 3. Add Phase C to Phase AB and mix well.

[0324] 4. Heat the formulation to 80 °C.

[0325] 5. Add the components of Phase D and mix well at 80 °C until uniformly dispersed.

[0326] 6. Cool the formulation to 45 °C with stirring.

[0327] 7. Premix Phase E in a separate container (using warm water to disperse)

[0328] 8. Add Phase E to Phase ABCD and mix well.

[0329] 9. Add the components of Phase F in the given order and mix well after each addition.

[0330] 10. Finally, add Phase G, mix well and store in a container.

[0331] Apply cream shampoo on dyed hair .

[0332] Single - bleached silver - gray hair tresses from International Hair Importers were dyed with Garnier Red 6.6. After that, the washed and dried hair tresses were divided into two halves. One half was washed with a cream shampoo containing the material according to Example 2, while the other half was washed with a control shampoo (without the additive of the present invention). After drying, the ΔE values of the hair tresses were recorded.

[0333] The above process was repeated 6 times.

[0334]

[0335] Example 4: Cream Shampoo

[0336] The experimental protocol outlined under Example 3 was repeated using the inventive compounds of Example 1.

[0337] The following results (ΔE) were obtained:

[0338]

[0339] Lower ΔE values after 6 washing cycles for shampoos containing the inventive compounds according to Examples 1 and 2 mean that less color is lost during the washing operation. The inventive ingredients improve the color retention of artificial hair.

[0340] In addition, it was observed that the hue of the red color on the half of the hair tresses treated with the material of the present invention was deeper and the color was more evenly distributed compared to the other half treated with the control shampoo.

Claims

1. Use of a compound of the following formula for treating hair: wherein R 5 is selected from hydroxy or F, provided that at least two of R 5 are F, wherein F is selected from: –O–C(O)–R 3 –R 4 , and –NR 1 –C(O)–R 3 –R 4 , wherein R 1 selected from hydrogen; n-, iso- or tert-C1-C 22 -alkyl, C2-C 22 -alkoxyalkyl, C5-C 30 -cycloalkyl, C6-C 30 -aryl, C6-C 30 -aryl(C1-C6)alkyl, C6-C 30 -alkylaryl, C2-C 22 -alkenyl, C2-C 22 -alkenyloxyalkyl, which may each optionally be substituted by hydroxyl and halogen, and which may optionally contain one or more ether groups (–O–), R 3 selected from single bonds and straight-chain, cyclic or branched, saturated or unsaturated hydrocarbon groups having up to 18 carbon atoms and optionally containing one or more groups selected from –O–, –NH–, –C(O)–, and wherein R 3 is optionally substituted with one or more groups selected from hydroxyl groups, amino groups, and carboxyl groups, and R 4 is a group of the formula: wherein R 10 , R 11 , R 12 , R 13 , R 14 are independently selected from R 1 , provided that 2-3 groups of R 10 -R 14 are hydroxyl groups, and wherein the dashed line represents a bond to R 3 , or, when R 3 is a single bond, is R 3 ; or R 4 is selected from di- and tri-hydroxy-substituted naphthyl groups, or a compound of the following formula: wherein R 6 one is a hydroxyl group and R 6 one is a group of the following formula wherein F is as defined above and the dashed line is a bond to a carbon atom, or a compound of the following formula: wherein x is from 1 to 10 and F is as defined above, wherein tannins are excluded from the compound.

2. The use according to claim 1, wherein R 4 is selected from a dihydroxyphenyl group, a trihydroxyphenyl group, a dihydroxynaphthyl group, and a trihydroxynaphthyl group.

3. Use according to claim 1, wherein the group R 1 The optional substituents are selected from hydroxyl and halogen and the group R 3 The optional substituents are selected from hydroxyl and amino, and the number of substituents can be up to 5.

4. The use according to claim 1, wherein the compound is a mixture of the following two isomers: wherein F is as defined in claim 1.

5. Use according to claim 1, wherein R 3 is a single bond or a vinylene group.

6. Use according to claim 1, wherein R 1 is hydrogen.

7. The use according to claim 2, wherein the dihydroxyphenyl group is selected from 2,3-dihydroxyphenyl, 2,4-dihydroxyphenyl, 2,5-dihydroxyphenyl, 2,6-dihydroxyphenyl, 3,4-dihydroxyphenyl, and 3,5-dihydroxyphenyl.

8. The use according to claim 2, wherein the trihydroxyphenyl group is selected from 2,3,4-trihydroxyphenyl, 2,3,5-trihydroxyphenyl, 2,3,6-trihydroxyphenyl, 2,4,5-trihydroxyphenyl, 2,4,6-trihydroxyphenyl, and 3,4,5-trihydroxyphenyl.

9. The use according to claim 2, wherein the dihydroxynaphthyl group is selected from 6,7-dihydroxynaphthyl, 5,6-dihydroxynaphthyl, 1,7-dihydroxynaphthyl, 3,7-dihydroxynaphthyl, 1,3-dihydroxynaphthyl, and 1,4-dihydroxynaphthyl.

10. The use according to claim 2, wherein the trihydroxynaphthyl group is selected from 4,6,7-trihydroxynaphthyl and 1,5,6-trihydroxynaphthyl.

11. The use according to claim 1, wherein R 4 is derived from a polyhydroxyaromatic carboxylic acid selected from polyhydroxybenzoic acid, polyhydroxycinnamic acid, and polyhydroxynaphthoic acid.

12. The use according to claim 11, wherein the polyhydroxybenzoic acid is selected from dihydroxybenzoic acid or trihydroxybenzoic acid.

13. The use according to claim 12, wherein the dihydroxybenzoic acid is selected from 2,3-dihydroxybenzoic acid, 2,4-dihydroxybenzoic acid, 2,5-dihydroxybenzoic acid, 2,6-dihydroxybenzoic acid, 3,4-dihydroxybenzoic acid, and 3,5-dihydroxybenzoic acid.

14. The use according to claim 12, wherein the trihydroxybenzoic acid is selected from 2,3,4-trihydroxybenzoic acid, 2,3,5-trihydroxybenzoic acid, 2,3,6-trihydroxybenzoic acid, 2,4,5-trihydroxybenzoic acid, 2,4,6-trihydroxybenzoic acid, and 3,4,5-trihydroxybenzoic acid.

15. The use according to claim 11, wherein the polyhydroxycinnamic acid is selected from dihydroxycinnamic acid or trihydroxycinnamic acid.

16. The use according to claim 15, wherein the dihydroxycinnamic acid is selected from 3,4-dihydroxycinnamic acid.

17. The use according to claim 15, wherein the trihydroxycinnamic acid is selected from 3,4,5-dihydroxycinnamic acid.

18. The use according to claim 11, wherein the polyhydroxynaphthoic acid is selected from dihydroxynaphthoic acid or trihydroxynaphthoic acid.

19. Use according to claim 18, wherein the dihydroxynaphthoic acid is selected from 6,7-dihydroxynaphthalene-2-carboxylic acid, 5,6-dihydroxynaphthalene-2-carboxylic acid, 1,7-dihydroxynaphthalene-2-carboxylic acid, 3,7-dihydroxynaphthalene-2-carboxylic acid, 1,3-dihydroxynaphthalene-2-carboxylic acid, and 1,4-dihydroxynaphthalene-2-carboxylic acid.

20. Use according to claim 18, wherein the trihydroxynaphthoic acid is selected from 4,6,7-trihydroxynaphthalene-2-carboxylic acid, and 1,5,6-trihydroxynaphthalene-2-carboxylic acid.

21. Use according to claim 3, wherein the number of substituents is 1 - 4.

22. The use according to claim 1, wherein R 1 is selected from hydrogen or n-, i- or t-C1-C 22 -alkyl.

23. Use according to claim 1, wherein x is 1 - 5.

24. Use according to claim 1, wherein for R 3 the defined hydrocarbon group has up to 12 carbon atoms.

25. Use according to claim 1, wherein for R 3 the defined hydrocarbon group has up to 10 carbon atoms.

26. The use according to claim 1, wherein for R 3 the defined unsaturated hydrocarbon group is an aromatic hydrocarbon group.

27. A compound of the following formula: wherein R 5 is selected from hydroxy or F, provided that at least two of R 5 are F, wherein F is selected from: –O–C(O)–R 3 –R 4 , and –NR 1 –C(O)–R 3 –R 4 , wherein R 1 selected from hydrogen; n-, iso- or tert-C1-C 22 -alkyl, C2-C 22 -alkoxyalkyl, C5-C 30 -cycloalkyl, C6-C 30 -aryl, C6-C 30 -aryl(C1-C6)alkyl, C6-C 30 -alkylaryl, C2-C 22 -alkenyl, C2-C 22 -alkenyloxyalkyl, which may each optionally be substituted by hydroxyl and halogen and which may optionally contain one or more ether groups (–O–), R 3 selected from single bonds and straight-chain, cyclic or branched, saturated or unsaturated hydrocarbon groups having up to 18 carbon atoms and optionally containing one or more groups selected from –O–, –NH–, –C(O)–, and wherein R 3 is optionally substituted with one or more groups selected from hydroxy groups, amino groups, and carboxyl groups, and R 4 is a group of the formula: wherein R 10 , R 11 , R 12 , R 13 , R 14 are independently selected from R 1 , provided that 2-3 groups of R 10 -R 14 are hydroxyl groups, and wherein the dashed line represents a bond to R 3 , or, when R 3 is a single bond, is R 3 ; or R 4 is selected from di- and tri-hydroxy-substituted naphthyl groups, or a compound of the following formula: wherein one of Rs 6 is hydroxyl and one of Rs 6 is a group of the following formula wherein F is as defined above and the dashed line is a bond to a carbon atom, or a compound of the following formula: wherein x is 1 - 10, and F is as defined above.

28. The compound according to claim 27, wherein the compound is a mixture of the following two isomers: wherein F is as defined in claim 27.

29. The compound according to claim 27, wherein R 3 is a single bond or a vinylene group.

30. The compound according to claim 27, wherein x is 1 - 5.

31. The compound according to claim 27, wherein for R 3 the defined unsaturated hydrocarbon group is an aromatic hydrocarbon group.

32. An aqueous composition comprising the compound according to any one of claims 27 - 31.

33. An aqueous composition comprising the compound as defined in any one of claims 1 - 31, and at least one other component selected from: a surfactant, and a metal salt.

34. The aqueous composition according to claim 33, which comprises at least one surfactant.

35. The aqueous composition according to claim 33, wherein the weight ratio of the surfactant and / or the metal salt to the compound is at least 0.

06.

36. The aqueous composition according to claim 33, which comprises 0.05 - 30% of the compound, where each percentage is by weight based on the total weight of the aqueous composition.

37. The aqueous composition according to claim 33, wherein the surfactant is selected from cationic, nonionic, betaine, and anionic surfactants.

38. The aqueous composition according to claim 37, wherein the surfactant has an HLB in the range of 1 - 20.

39. The aqueous composition according to claim 33, wherein the surfactant is selected from hydrocarbon-based or silicone-based emulsifiers.

40. The aqueous composition according to claim 33, wherein the surfactant is present in an amount of 0.05% - 15% by weight of the aqueous composition.

41. The aqueous composition according to claim 33, which comprises at least one additional additive selected from: a) an organic diluent or solvent, b) a protein, c) a softening agent or a fatty substance, d) a preservative, e) a skin protection component, f) a conditioning agent, g) an oxidizing agent, h) a reducing agent, i) a tannin, j) a metal salt, k) other auxiliaries selected from the following: pH regulators, thickeners, lipids, amino acids, sugars, fragrances, sunscreens, vitamins, pearlescent agents, gelling agents, trace elements, masking agents, antioxidants, humectants, anti - hair loss agents, anti - dandruff agents, propellants, ceramides, polymers, fillers, nacre, colorants, and mixtures thereof, provided that an oxidizing agent and a reducing agent are not present simultaneously in the given composition.

42. The aqueous composition according to claim 41, wherein the polymer is a film - forming polymer.

43. The aqueous composition according to claim 33, having the following composition: wherein the weight percentages relate to the total weight of the aqueous composition.

44. The aqueous composition according to claim 33, wherein the metal salt is Zn 2+ , Fe 2+ and / or Fe 3+ salt.

45. The aqueous composition according to claim 33, wherein the weight ratio of the surfactant and / or metal salt to the compound is 0.06 - 5.

46. The aqueous composition according to claim 33, wherein the weight ratio of the surfactant and / or metal salt to the compound is 0.06 - 3.

47. The aqueous composition according to claim 33, wherein the weight ratio of the surfactant and / or metal salt to the compound is 0.1 - 3.

48. The aqueous composition according to claim 33, wherein the weight ratio of the surfactant and / or metal salt to the compound is 0.1 - 1.

49. The aqueous composition according to claim 33, which comprises 0.5 - 30% of the compound, wherein each percentage is by weight based on the total weight of the aqueous composition.

50. The aqueous composition according to claim 33, which comprises 1 - 30% of the compound, wherein each percentage is by weight based on the total weight of the aqueous composition.

51. The aqueous composition according to claim 33, which comprises 1 - 20% of the compound, wherein each percentage is by weight based on the total weight of the aqueous composition.

52. The aqueous composition according to claim 33, which comprises 1 - 10% of the compound, wherein each percentage is by weight based on the total weight of the aqueous composition.

53. The aqueous composition according to claim 37, wherein the surfactant has an HLB in the range of 7 - 20.

54. The aqueous composition according to claim 37, wherein the surfactant has an HLB in the range of 8 - 20.

55. The aqueous composition according to claim 33, wherein the surfactant is present in an amount of 0.05% - 5% by weight of the aqueous composition.

56. The aqueous composition according to claim 33, wherein the surfactant is present in an amount of 0.1% - 5% by weight of the aqueous composition.

57. The aqueous composition according to claim 33, wherein the surfactant is present in an amount of 0.1 - 3% by weight of the aqueous composition.

58. The aqueous composition according to claim 41, wherein the colorant is selected from pigments and dyes.

59. The aqueous composition according to claim 41, wherein the amount of the compound is 1 - 10% by weight.

60. The aqueous composition according to claim 43, wherein the amount of the hydrocarbon- or silicone-based surfactant is 0.05 - 5% by weight.

61. The aqueous composition according to claim 43, wherein the amount of the diluent / solvent is 0.1 - 95% by weight.

62. The aqueous composition according to claim 43, wherein the amount of the diluent / solvent is 10 - 95% by weight.

63. The aqueous composition according to claim 43, wherein the amount of the diluent / solvent is 20 - 95% by weight.

64. The aqueous composition according to claim 43, wherein the amount of the diluent / solvent is 20 - 50% by weight.

65. The aqueous composition according to claim 43, wherein the amount of the diluent / solvent is 50 - 95% by weight.

66. The aqueous composition according to claim 41, wherein the protein is keratin.

67. The aqueous composition according to claim 41, wherein the amount of the protein is 0 - 10% by weight.

68. The aqueous composition according to claim 41, wherein the amount of the protein is 0.01 - 5% by weight.

69. The aqueous composition according to claim 41, wherein the amount of the emollient / fatty substance is 0 - 10% by weight.

70. The aqueous composition according to claim 41, wherein the amount of the emollient / fatty substance is 0 - 5% by weight.

71. The aqueous composition according to claim 41, wherein the amount of the emollient / fatty substance is 0.01 - 5% by weight.

72. The aqueous composition according to claim 41, wherein the amount of the preservative is 0 - 3% by weight.

73. The aqueous composition according to claim 41, wherein the amount of the preservative is 0 - 2% by weight.

74. The aqueous composition according to claim 41, wherein the amount of the preservative is 0.01 - 2.5% by weight.

75. The aqueous composition according to claim 41, wherein the amount of the skin protecting ingredient is 0 - 10% by weight.

76. The aqueous composition according to claim 41, wherein the amount of the skin protecting ingredient is 0 - 5% by weight.

77. The aqueous composition according to claim 41, wherein the amount of the skin protecting ingredient is 0 - 1% by weight.

78. The aqueous composition according to claim 41, wherein the amount of the skin protecting ingredient is 0 - 0.1% by weight.

79. The aqueous composition according to claim 41, wherein the amount of the skin protecting ingredient is 0.01 - 5% by weight.

80. The aqueous composition according to claim 41, wherein the amount of the conditioner is 0 - 10% by weight.

81. The aqueous composition according to claim 41, wherein the amount of the conditioner is 0 - 5% by weight.

82. The aqueous composition according to claim 41, wherein the amount of the conditioner is 0 - 1% by weight.

83. The aqueous composition according to claim 41, wherein the amount of the conditioner is 0 - 0.1% by weight.

84. The aqueous composition according to claim 41, wherein the amount of the conditioning agent is 0.01 - 5% by weight.

85. The aqueous composition according to claim 41, wherein the amount of the oxidizing agent is 0 - 10% by weight.

86. The aqueous composition according to claim 41, wherein the amount of the oxidizing agent is 0 - 5% by weight.

87. The aqueous composition according to claim 41, wherein the amount of the oxidizing agent is 0 - 2% by weight.

88. The aqueous composition according to claim 41, wherein the amount of the oxidizing agent is 0.01 - 5% by weight.

89. The aqueous composition according to claim 41, wherein the amount of the reducing agent is 0 - 10% by weight.

90. The aqueous composition according to claim 41, wherein the amount of the reducing agent is 0 - 5% by weight.

91. The aqueous composition according to claim 41, wherein the amount of the reducing agent is 0 - 2% by weight.

92. The aqueous composition according to claim 41, wherein the amount of the reducing agent is % by weight.

93. The aqueous composition according to claim 41, wherein the amount of the tannin is 0 - 10% by weight.

94. The aqueous composition according to claim 41, wherein the amount of the tannin is 0 - 5% by weight.

95. The aqueous composition according to claim 41, wherein the amount of the tannin is 0 - 2% by weight.

96. The aqueous composition according to claim 41, wherein the amount of the tannin is 0.01 - 5% by weight.

97. The aqueous composition according to claim 41, wherein the metal salt is selected from iron or zinc salts.

98. The aqueous composition according to claim 41, wherein the amount of the metal salt is 0 - 10% by weight.

99. The aqueous composition according to claim 41, wherein the amount of the metal salt is 0 - 5% by weight.

100. The aqueous composition according to claim 41, wherein the amount of the metal salt is 0 - 2% by weight.

101. The aqueous composition according to claim 41, wherein the amount of the metal salt is 0.01 - 5% by weight.

102. The aqueous composition according to claim 43, wherein the amount of the hair dye is 0 - 10% by weight.

103. The aqueous composition according to claim 43, wherein the amount of the hair dye is 0 - 5% by weight.

104. The aqueous composition according to claim 43, wherein the amount of the hair dye is 0 - 2% by weight.

105. The aqueous composition according to claim 43, wherein the amount of the hair dye is 0.01 - 5% by weight.

106. The aqueous composition according to claim 41, wherein the amount of the other auxiliaries is 0 - 10% by weight.

107. The aqueous composition according to claim 41, wherein the amount of the other auxiliaries is 0 - 5% by weight.

108. The aqueous composition according to claim 41, wherein the amount of the other auxiliaries is 0 - 2% by weight.

109. The aqueous composition according to claim 41, wherein the amount of the other auxiliaries is 0.01 - 5% by weight.

110. A cosmetic composition comprising at least one compound according to any one of claims 27 - 31, or at least one aqueous composition according to any one of claims 32 - 109.

111. The cosmetic composition according to claim 110, which is used in hair treatment.

112. The cosmetic composition according to claim 111, which is selected from hair shampoo compositions, hair care compositions, hair conditioning compositions, hair strengthening compositions, hair coloring or dyeing compositions, hair combability improving compositions, anti - frizz compositions, hair rinse and leave - in compositions.

113. The cosmetic composition according to claim 111, which is used in hair coloring treatment.

114. A method for treating hair, which comprises the steps of: providing a cosmetic composition according to claim 110, and applying the cosmetic composition to the hair.

115. The method for treating hair according to claim 114, which further comprises the step of dyeing the hair.

116. The method for treating hair according to claim 114, which comprises the following steps: - contacting the hair with a cosmetic composition according to claim 110, - optionally contacting the hair with a composition containing a metal salt of Fe and / or Zn, and - drying the hair.

117. Use of an aqueous composition according to any one of claims 32 - 109 for treating hair.

118. The use according to claim 117, which is for hair strengthening, for hair color retention, for hair color enhancement, for hair color protection, for hair shaping, for hair conditioning, for hair smoothing or softening, for improving hair manageability.

119. The use according to claim 118, wherein the hair shaping is hair curling and straightening.

120. The use according to claim 118, which is for improving hair combability.

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