WO2025003165A1

WO2025003165A1 - Process for treating keratin fibres using a composition comprising at least one particular fatty acid, at least one oxygenated terpene compound and at least one oligo/poly-ester

Info

Publication number: WO2025003165A1
Application number: PCT/EP2024/067861
Authority: WO
Inventors: Fatima Makhlouf; Stéphane SABELLE
Original assignee: LOreal SA
Current assignee: LOreal SA
Priority date: 2023-06-30
Filing date: 2024-06-25
Publication date: 2025-01-02
Anticipated expiration: 2025-12-30

Abstract

The present invention relates to a process for treating keratin fibres using a composition comprising at least one particular fatty acid, at least one oxygenated terpene compound and at least one oligo/poly-ester.

Description

PROCESS FOR TREATING KERATIN FIBRES USING A COMPOSITION COMPRISING AT LEAST ONE PARTICULAR FATTY ACID, AT LEAST ONE OXYGENATED TERPENE COMPOUND AND AT LEAST ONE OLIGO/POLY-ESTER

TECHNICAL FIELD OF THE INVENTION

BACKGROUND OF THE INVENTION

The hair is damaged and weakened by external atmospheric agents such as pollution and bad weather, and also by mechanical or chemical treatments, such as brushing, combing, dyeing, bleaching, permanent-waving, relaxing and repeated washing. The hair thus becomes damaged and may in the long run become dry, coarse, brittle, dull, split and/or soft or else sensitive to humidity, making the hair unmanageable, often with frizziness, and/or difficult to style in a humid environment, in particular in a very humid environment.

Thus, to overcome these drawbacks, it is common practice to resort to hair treatments which make use of compositions intended for conditioning the hair appropriately by giving it satisfactory cosmetic properties, notably a soft feel (the hair is no longer coarse), good disentangling properties leading to easy combing, and good manageability of the hair which is thus easy to shape.

However, these hair treatments, which are often based on silicone-based starting materials, may give the hair a greasy, heavy feel that is not always pleasant for the user. Moreover, these hair treatments have little or no effect on controlling the volume of keratin fibres and/or maintaining the hairstyle and/or hair discipline in a humid or very humid environment.

Moreover, the formulation of environmentally-friendly cosmetic products, i.e. products whose design and development take account of environmental issues, is becoming a major preoccupation for contributing towards meeting the global challenges. It thus proves essential to propose more sustainable compositions, thereby enabling these environmental challenges to be met notably by reducing the use of compounds of petrochemical origin.

There is thus a real need to develop a hair treatment process that can remedy these drawbacks and that is notably capable of preserving or even improving the quality of the fibre, notably the softness, disentangling, smoothness, discipline and/or sheen, and of durably limiting the formation of frizziness and/or the increase in volume of the head of hair in a humid environment so as to facilitate styling of the hair in a humid environment. Such a process must ideally not use any silicone starting materials.

The Applicant has discovered, surprisingly, that all or some of these objectives can be achieved by the process according to the present invention.

SUMMARY OF THE INVENTION

According to a first aspect, a subject of the present invention is a process for treating keratin fibres, comprising step i) of applying to the keratin fibres a composition (C) comprising:
a) one or more compounds A chosen from the compounds of formula (I) below, salts thereof, isomers thereof, solvates thereof such as hydrates and mixtures thereof:

in which formula (I):
▪ R¹ represents:
- a linear or branched, saturated or unsaturated hydrocarbon-based group comprising from 6 to 26 carbon atoms, the hydrocarbon-based group being optionally substituted with one or more identical or different groups chosen from: hydroxyl (-OH), amino (-NH₂), carboxyl (-COOH), (hetero)cyclic such as phenyl and/or optionally interrupted with one or more heteroatoms or groups chosen from -O-, -CO-, -NR^a-, or combinations thereof such as -O-CO-, -(CO)-O-, –NR^a-(CO)– or –(CO)-NR^a–; or
- a (hetero)cyclic group such as phenyl, optionally substituted with one or more identical or different groups chosen from: hydroxyl (-OH) or R^b-(CO)-;
▪ R^a represents a hydrogen atom or a linear or branched, saturated or unsaturated hydrocarbon-based group comprising from 1 to 10 carbon atoms optionally substituted with one or more identical or different groups chosen from (-OH), amino (-NH₂) or carboxyl (-COOH);
▪ R^b represents a (C₂-C₁₀)alkyl group; and
b) one or more compounds B chosen from oxygenated terpene compounds, preferably chosen from menthol, menthone, terpineol, isoborneol, camphor, nerol, citronellal, citronellol, myrcenol, linalool, geraniol, vitamin A, carvone, eugenol, thymol, fenchone, borneol, eucalyptol, cubebol, farnesol, patchoulol, viridiflorol, cafestol, ferruginol, isomers thereof, solvates thereof such as hydrates and mixtures thereof; and
c) one or more compounds E chosen from oligoesters, polyesters and mixtures thereof.

According to a second aspect, a subject of the present invention is a composition (C) as defined previously.

According to a third aspect, a subject of the present invention is the use of a composition (C) as defined previously for caring for keratin fibres, preferably for giving keratin fibres a soft and/or smooth feel and/or sheen, more preferentially for giving them a soft and/or smooth feel.

According to a fourth aspect, a subject of the present invention is the use of a composition (C) as defined previously for protecting keratin fibres from moisture, preferably for limiting the formation of frizziness and/or the increase in volume of the head of hair in a humid environment.

DETAILED DESCRIPTION OF THE INVENTION

For the purposes of the present invention and unless otherwise indicated:

▪ the term “keratin fibres” means fibres of human or animal origin, such as head hair, bodily hairs, the eyelashes, the eyebrows, wool, angora, cashmere or fur. According to the present invention, the keratin fibres are preferably human keratin fibres, more preferentially the head hair.

▪ the term “alkyl group” means a saturated, linear or branched hydrocarbon-based radical comprising from 1 to 30 carbon atoms, preferentially from 1 to 26 carbon atoms, more preferentially from 1 to 22 carbon atoms, for example methyl, ethyl, n-propyl, isopropyl, butyl, n-pentyl, n-hexyl, n-decyl, n-undecyl, n-dodecyl, n-tetradecyl, n-hexadecyl or eicosyl.

▪ the term “(C_x-C_y)alkyl group” means an alkyl group comprising from x to y carbon atoms.

▪ the term “hydroxy(C_x-C_y)alkyl group” means a (C_x-C_y)alkyl group, at least one of the hydrogen atoms of which is optionally replaced with a hydroxyl (-OH) group. A “(hydroxy)(C_x-C_y)alkyl group” thus denotes a (C_x-C_y)alkyl group or a hydroxyl(C_x-C_y)alkyl group, i.e. a (C_x-C_y)alkyl group in which at least one of the hydrogen atoms is replaced with a hydroxyl (-OH) group.

▪ the term “di(hydroxy)(C_x-C_y)alkylammonium salt” means an ammonium salt bearing two (hydroxyl)(C_x-C_y)alkyl groups, said (hydroxyl)(C_x-C_y)alkyl groups being identical or different.

▪ the term “tri(hydroxy)(C_x-C_y)alkylammonium salt” means an ammonium salt bearing three (hydroxyl)(C_x-C_y)alkyl groups, said (hydroxyl)(C_x-C_y)alkyl groups being identical or different.

▪ the term “tetra(hydroxy)(C_x-C_y)alkylammonium salt” means an ammonium salt bearing four (hydroxyl)(C_x-C_y)alkyl groups, said (hydroxyl)(C_x-C_y)alkyl groups being identical or different.

▪ the term “(hetero)cyclic group” means a cyclic or heterocyclic group.

▪ the term “cyclic group” means a monocyclic or condensed or non-condensed, saturated or unsaturated, notably aromatic, polycyclic carbocycle comprising from 6 to 22 carbon atoms, it being possible for said cyclic group to be substituted with one or more identical or different groups, notably chosen from: (C₁-C₆)alkyl, (C₁-C₆)alkoxy, (C₁-C₆)(poly)hydroxyalkyl, hydroxyl (-OH) or carboxyl (-COOH).

▪ the term “heterocyclic group” means a monocyclic or condensed or non-condensed, saturated or unsaturated, notably aromatic, polycyclic group comprising from 5 to 22 members and containing from 1 to 3 heteroatoms chosen from a nitrogen, oxygen or sulfur atom, it being possible for said heterocyclic group to be substituted with one or more identical or different groups, notably chosen from: (C₁-C₆)alkyl, (C₁-C₆)alkoxy, (C₁-C₆)(poly)hydroxyalkyl, hydroxyl (-OH) or carboxyl (-COOH).

▪ the term “unsaturated hydrocarbon-based group” means a hydrocarbon-based group comprising one or more conjugated or non-conjugated ethylenic double bonds.

▪ the term “oligoester” means a hydrocarbon-based chain comprising from 2 to 10 ester units (ester units also known as ester monomers), which may be identical or different.

▪ the term “polyester” means a hydrocarbon-based chain comprising more than 11 identical or different ester units (ester units also known as ester monomers).

▪ the term “isomer” means an optical, geometrical or tautomeric isomer.

The terms “at least one” and “one or more” are synonymous and may be used interchangeably.

Process for treating keratin fibres

According to a first aspect, a subject of the present invention is a process for treating keratin fibres as defined previously.

The Applicant has found, surprisingly, that the process according to the present invention made it possible to maintain or even improve the quality of the fibre, notably the softness, disentangling, smoothness and/or discipline and/or sheen, and to limit the formation of frizziness and/or the increase in volume of the head of hair in a humid environment, thus making it easier to style the hair in a humid environment.

Composition (C) preferably comprises not more than five different compounds A, more preferentially not more than four different compounds A, even more preferentially not more than two different compounds A, and better still composition (C) comprises only one compound A chosen from the compounds of formula (I) as defined previously, the salts thereof, the isomers thereof, and the solvates thereof such as hydrates, and mixtures thereof.

Composition (C) preferably comprises not more than five different compounds B, more preferentially not more than four different compounds B, even more preferentially not more than two different compounds B, and better still composition (C) comprises only one compound B as defined previously.

According to a preferred embodiment, composition (C) comprises a single compound A as defined previously and a single compound B as defined previously.

Preferably, at least one of the compounds A, preferably all of the compounds A, are present in composition (C) in non-salified form.

According to a preferred embodiment, the mole ratio of the total amount of compounds A to the total amount of compounds B present in composition (C) is less than or equal to 1, more preferably ranging from 1 to 0.25.

Compounds A

Composition (C) comprises a) one or more compounds A chosen from the compounds of formula (I) as defined previously, salts thereof, isomers thereof, solvates thereof such as hydrates and mixtures thereof.

Preferably, the salts of the compounds of formula (I) are chosen from the monovalent salts of the compounds of formula (I).

More preferentially, the salts of the compounds of formula (I) are chosen from salts of alkali metals such as sodium or potassium, ammonium salts and tetra(C₁-C₁₀)alkylammonium salts, di(C₁-C₁₀)alkylammonium salts, tri(C₁-C₁₀)alkylammonium salts, and mixtures thereof, preferably chosen from salts of alkali metals such as sodium or potassium, tetra(C₁-C₁₀)alkylammonium salts, and mixtures thereof.

According to a preferred embodiment, R¹ represents a linear or branched, saturated or unsaturated hydrocarbon-based group comprising from 6 to 26 carbon atoms, the hydrocarbon-based group being optionally substituted with one or more identical or different groups chosen from: hydroxyl (-OH), amino (-NH₂), carboxyl (-COOH), (hetero)cyclic such as phenyl and/or optionally interrupted with one or more heteroatoms or groups chosen from -O-, -CO-, –NR^a–, or combinations thereof such as -O-CO-, -(CO)-O-, –NR^a-(CO)– or –(CO)-NR^a–, R^a being as defined previously, preferably an unsubstituted, saturated or unsaturated, linear or branched hydrocarbon-based group comprising from 6 to 26 carbon atoms, more preferentially an unsubstituted, saturated or unsaturated, linear or branched hydrocarbon-based group comprising from 6 to 20 carbon atoms, even more preferentially a (C₆-C₂₀)alkyl group, most preferentially a (C₆-C₁₂)alkyl group.

According to a preferred embodiment, the compound(s) A are chosen from the following compounds 1 to 39, the salts thereof, the isomers thereof, and the solvates thereof such as hydrates, and mixtures thereof:

According to a more preferred embodiment, the compound(s) A are chosen from compounds 1 to 20, 22, 25, 26, 28, 31, 32, 36 or 39, the salts thereof, the isomers thereof, and the solvates thereof such as hydrates, and mixtures thereof.

According to an even more preferred embodiment, the compound(s) A are chosen from compounds 4, 16 or 17, the salts thereof, the isomers thereof, and the solvates thereof such as hydrates, and mixtures thereof.

According to an even more preferred embodiment, the compound(s) A are chosen from compounds 16 or 17, the salts thereof, the isomers thereof, and the solvates thereof such as hydrates, and mixtures thereof.

According to a preferred variant, the compound(s) A are chosen from compounds 1 to 39, isomers thereof, solvates thereof such as hydrates thereof and mixtures thereof, preferably from compounds 1 to 20, 22, 25, 26, 28, 31, 32, 36 or 39, isomers thereof, solvates thereof such as hydrates thereof and mixtures thereof, more preferentially from compounds 4, 16 or 17, isomers thereof, solvates thereof such as hydrates and mixtures thereof, most preferentially from compounds 16 or 17, isomers thereof, solvates thereof such as hydrates and mixtures thereof.

When one or more of the compounds A are in salified form, they are preferably chosen from the following compounds 1’ to 11’, the isomers thereof and the solvates thereof, such as hydrates, and mixtures thereof:

with X⁺ representing a preferably monovalent cation, more preferentially a monovalent cation derived from a salt chosen from salts of alkali metals such as sodium or potassium, ammonium salts, tetra(hydroxy)(C₁-C₁₀)alkylammonium salts, di(hydroxy)(C₁-C₁₀)alkylammonium salts, tri(hydroxy)(C₁-C₁₀)alkylammonium salts, and mixtures thereof, even more preferentially a monovalent cation derived from a salt chosen from salts of alkali metals such as sodium or potassium, tetra(hydroxy)(C₁-C₁₀)alkylammonium salts, and mixtures thereof.

When one or more of the compounds A are in salified form, they are more preferentially chosen from compounds 1’ to 11’, the isomers thereof and the solvates thereof, such as hydrates, and mixtures thereof, with X⁺ representing a monovalent cation derived from a salt chosen from salts of alkali metals such as sodium or potassium, ammonium salts, tetra(C₁-C₁₀)alkylammonium salts, di(C₁-C₁₀)alkylammonium salts, tri(C₁-C₁₀)alkylammonium salts, and mixtures thereof, preferably chosen from salts of alkali metals such as sodium or potassium, tetra(C₁-C₁₀)alkylammonium salts, and mixtures thereof.

When one or more of the compounds A are in salified form, they are even more preferentially chosen from compounds 1’ to 11’, the isomers thereof and the solvates thereof, such as hydrates, and mixtures thereof, with X⁺ representing an Na⁺, K⁺, NH₄ ⁺ or tetra(C₁-C₁₀)alkylammonium ion.

When one or more of the compounds A are in salified form, they are more preferentially chosen from the following compounds 1’’ to 13’’, the isomers thereof and the solvates thereof, such as hydrates, and mixtures thereof:

According to a particularly preferred embodiment, when one or more of the compounds A are in salified form, they are chosen from compounds 5’’, 6’’, the isomers thereof and the solvates thereof, such as hydrates, and mixtures thereof.

Preferably, composition (C) comprises a total content of compounds A ranging from 0.01% to 99%, preferably ranging from 0.5% to 99% by weight, more preferentially ranging from 2% to 98% by weight, even more preferentially ranging from 2.5% to 80% by weight, relative to the total weight of composition (C).

Compounds B

Composition (C) comprises b) one or more compounds B chosen from oxygenated terpene compounds, preferably chosen from menthol, menthone, terpineol, isoborneol, camphor, nerol, citronellal, citronellol, myrcenol, linalool, geraniol, vitamin A, carvone, eugenol, thymol, fenchone, borneol, eucalyptol, cubebol, farnesol, patchoulol, viridiflorol, cafestol, ferruginol, isomers thereof, solvates thereof such as hydrates and mixtures thereof.

According to a preferred embodiment, the compound(s) B are chosen from menthol, menthone, terpineol, isoborneol, camphor, nerol, citronellal, citronellol, myrcenol, linalool, geraniol, vitamin A, carvone, eugenol, thymol, fenchone, borneol, eucalyptol, isomers thereof, solvates thereof such as hydrates and mixtures thereof, preferably from menthol, thymol, isomers thereof, solvates thereof such as hydrates and mixtures thereof, more preferentially from menthol, isomers thereof, solvates thereof such as hydrates and mixtures thereof.

Preferably, composition (C) comprises a total content of compounds B ranging from 0.01% to 99%, preferably ranging from 0.5% to 99% by weight, more preferentially ranging from 2% to 98% by weight, even more preferentially ranging from 2.5% to 80% by weight, relative to the total weight of composition (C).

According to a preferred embodiment:
- compound A is capric acid and compound B is menthol, the mole ratio of the total amount of capric acid to the total amount of menthol in composition (C) preferably being less than or equal to 1, more preferentially equal to 1/2; or
- compound A is lauric acid and compound B is menthol, the mole ratio of the total amount of lauric acid to the total amount of menthol in composition (C) preferably being less than or equal to 1, more preferentially equal to 1/2; or
- compound A is caprylic acid and compound B is menthol, the mole ratio of the total amount of caprylic acid to the total amount of menthol in composition (C) preferably being less than or equal to 1, more preferentially equal to 1/2 or 1/4 or 1, even more preferentially equal to 1.

According to a more preferred embodiment:
- compound A is capric acid and compound B is menthol, the mole ratio of the total amount of capric acid to the total amount of menthol in composition (C) preferably being less than or equal to 1, more preferentially equal to 1/2; or
- compound A is caprylic acid and compound B is menthol, the mole ratio of the total amount of caprylic acid to the total amount of menthol in composition (C) preferably being less than or equal to 1, more preferentially equal to 1/2 or 1/4 or 1, even more preferentially equal to 1.

According to an even more preferred embodiment, compound A is caprylic acid and compound B is menthol, the mole ratio of the total amount of caprylic acid to the total amount of menthol in composition (C) preferably being less than or equal to 1, more preferably equal to 1/2 or 1/4 or 1, even more preferentially equal to 1.

Preferably, composition (C) comprises a total content of compounds A and B of at least 0.02% by weight, preferably at least 0.1% by weight, more preferentially at least 0.5% by weight, even more preferentially at least 1% by weight, most preferentially at least 2% by weight, better still at least 3% by weight, and even better still at least 4% by weight relative to the total weight of composition (C).

According to a preferred embodiment, composition (C) comprises a total content of compounds A and B ranging from 0.02% to 99.9% by weight, preferably ranging from 0.1% to 99% by weight, more preferentially ranging from 0.5% to 99% by weight, even more preferentially ranging from 1% to 99% by weight, most preferentially ranging from 2% to 99% by weight, better still ranging from 3% to 99% by weight, and even better still ranging from 4% to 99% by weight relative to the total weight of composition (C).

Compounds E

Composition (C) also comprises one or more compounds E chosen from oligoesters, polyesters and mixtures thereof.

The compound(s) E are preferably derived from:
- reaction of one or more polyols and one or more compounds chosen from carboxylic acids F comprising one or more carboxyl groups, carboxylic acid anhydrides and mixtures thereof; and/or
- polycondensation of one or more hydroxy acids; and/or
- ring-opening polymerization of one or more lactones.

Polyols

According to a particular embodiment, the compound(s) E are obtained from one or more polyols preferably comprising from 2 to 6 hydroxyl (-OH) groups, in particular two or four hydroxyl groups.

Preferably, the polyol(s) are green, in particular of natural origin, in particular biobased and notably of plant origin.

According to a particular embodiment, the polyol(s) are organic compounds comprising a linear or branched, acyclic or (poly)cyclic, saturated or unsaturated, aromatic or non-aromatic hydrocarbon-based chain comprising from 3 to 18 carbon atoms, in particular from 4 to 12 carbon atoms, or even from 5 to 10 carbon atoms; and from 2 to 6 hydroxyl groups, in particular from 3 to 6 hydroxyl groups, said hydrocarbon-based chain being optionally interrupted with one or more heteroatoms, notably oxygen heteroatoms, in particular possibly bearing ether functions. As examples of such polyols, mention may be made, without this list being limiting, of i) oses, notably pentoses such as ribose, arabinose, xylose, lyxose, ribulose, xylulose or hexoses such as allose, altrose, galactose, glucose, idose, mannose, talose, fructose, sorbose or even deoxyhexoses such as fucose or rhamnose; ii) triols such as glycerol, iii) tetraols such as pentaerythritol (tetramethylolmethane), erythritol, diglycerol, iv) pentols such as xylitol, v) hexols such as sorbitol and mannitol, or even dipentaerythritol or triglycerol, and mixtures thereof.

According to a particular embodiment, the polyol(s) are oligomers derived from one or more diols of formula (II) HO-ALK-OH, in which formula (II) ALK represents a linear or branched C1-C18, in particular C1-C6, alkylene group, optionally substituted with one or more hydroxyl groups, in particular one hydroxyl group. The polyol(s) are then poly(C₁-C₁₈)alkanediols. In particular, the polyol(s) may be oligomers derived from one or more diols of the abovementioned formula (II) with a weight-average molecular mass of between 200 and 4000 g.mol^-1, in particular between 300 and 3000 g.mol^-1. By way of example, the compound of formula (II) is such that ALK represents a (C₁-C₆)alkylene group, the oligomer then being a poly(C₁-C₆)alkane diol. Mention may notably be made of polypropanediol (also known as polypropylene glycol) with a weight-average molecular mass of between 300 and 3000 g.mol^-1, or polyethylene glycol with a weight-average molecular mass of between 300 and 3000 g.mol^-1.

According to another particular embodiment, the polyol(s) may be chosen from monosaccharide or polysaccharide sugars.

According to a preferred embodiment, the compound(s) E are obtained from one or more organic polyols chosen from:
- diols and triols, such as propanediols, butanediols such as 1,4-butanediol, hexanediols, dilinoleic dimer alcohols, glycerol, diethylene glycol, neopentyl glycol, tricyclodecanedimethanol, trihydroxystearin, or 2-(dihydroxymethyl)butan-1-ol;
- tetraols such as pentaerythritol (tetramethylolmethane), erythritol or diglycerol;
- pentols such as xylitol;
- hexols such as sorbitol, mannitol or dipentaerythritol;
- polyglycerol-3, polyglycerol-6 or polyglycerol-10; and
- mixtures thereof.

According to a more preferred embodiment, the compound(s) E are obtained from one or more organic polyols chosen from:
- diols and triols, such as propanediols, butanediols such as 1,4-butanediol, hexanediols, dilinoleic dimer alcohols, glycerol, diethylene glycol, neopentyl glycol, tricyclodecanedimethanol, trihydroxystearin, or 2-(dihydroxymethyl)butan-1-ol;
- tetraols such as pentaerythritol (tetramethylolmethane), erythritol or diglycerol;
- polyglycerol-3, polyglycerol-6 or polyglycerol-10; and
- mixtures thereof.

According to an even more preferred embodiment, the compound(s) E are obtained from one or more organic polyols chosen from:
- diols and triols chosen from propanediols, butanediols such as 1,4-butanediol, hexanediols, dilinoleic dimer alcohols, glycerol, diethylene glycol, neopentyl glycol or tricyclodecanedimethanol;
- pentaerythritol (tetramethylolmethane), erythritol or diglycerol;
- polyglycerol-3; and
- mixtures thereof.

Polyacids F

According to a particular embodiment, the compound(s) E are obtained from one or more polycarboxylic acids, also referred to in the text hereinbelow as “polyacids”, i.e. comprising at least two carboxyl groups.

The polyacid(s) may be acyclic or (poly)cyclic, saturated or unsaturated, aromatic or non-aromatic, linear or branched, and comprise at least two -C(O)OH carboxyl groups, in particular two to four -C(O)OH groups and more particularly two -C(O)OH groups.

The polyacid(s) are preferably chosen from polycarboxylic acids comprising at least two -C(O)OH carboxyl groups, in particular from 2 to 4 carboxyl groups, notably 2 carboxyl groups and comprising a total number of carbon atoms (carbon atoms of the carboxyl groups included) ranging from 2 to 54, notably ranging from 2 to 50 and more particularly ranging from 3 to 40, and even more particularly ranging from 3 to 36.

When the polyacid(s) comprise two carboxyl groups, they are referred to as dicarboxylic acids or diacids.

According to a particular embodiment, the polyacid(s) may be chosen from polycarboxylic acids, in particular dicarboxylic acids, with a molecular mass MM of less than or equal to 200 g.mol^-1.

In particular, the polyacid(s) may be chosen from oxalic acid, succinic acid, adipic acid, fumaric acid, phthalic acid, terephthalic acid, isomers thereof, salts thereof with organic or mineral bases, solvates thereof such as hydrates and mixtures thereof.

According to a particular embodiment, the polyacid(s) may be chosen from polycarboxylic acids, in particular dicarboxylic acids, with a molecular mass MM of greater than 200 g.mol^-1.

In particular, the polyacid(s) may be chosen from fatty polyacids, in particular fatty diacids, and notably from fatty acid dimers.

The term “fatty (poly)acid ” means a (poly)carboxylic acid comprising at least one linear or branched, preferably linear, saturated or unsaturated hydrocarbon-based chain which may contain at least one carbocycle, in particular one or two carbocycles, notably of the monocyclic or polycyclic cycloalkyl type, for example cyclohexyl or decalinyl (cis or trans decalinyl) and comprising a total number of carbon atoms (carbon atoms of the carboxyl group(s) included) ranging from 8 to 38, in particular ranging from 8 to 36, notably ranging from 10 to 36.

Preferably, the total number of carbon atoms in the fatty (poly)acid is even.

According to a particular embodiment, the polyacid(s) are chosen from the compounds of the following formula (III), salts thereof with organic or inorganic bases, solvates thereof such as hydrates and mixtures thereof: HO-C(O)-ALK'-C(O)-OH (III), in which ALK' represents a linear or branched, preferably linear, saturated or unsaturated hydrocarbon-based chain which may contain at least one carbocycle, in particular one or two carbocycles, notably of the monocyclic or polycyclic cycloalkyl type, for example cyclohexyl or decalinyl (cis or trans decalinyl), the hydrocarbon-based chain comprising a total number of carbon atoms ranging from 6 to 36, in particular ranging from 6 to 34, notably ranging from 8 to 34.

As examples of fatty polyacids, mention may be made of sebacic acid and fatty acid dimers. The term “fatty acid dimer” refers to the product of dimerization of mono- or polyunsaturated fatty acids.

The fatty acids from which the fatty acid dimers can be prepared may be chosen more particularly from oleic acid, linoleic acid, palmitoleic acid, linolenic acid, eleostearic acid and mixtures thereof.

The polyacid(s) may be chosen from fatty acid dimers comprising a total number of carbon atoms ranging from 18 to 38, in particular from 34 to 38 and more particularly 36 carbon atoms.

In particular, the fatty acid dimers may be chosen from the compounds of formula (III) as defined previously, in which ALK' represents a hydrocarbon-based chain comprising a total number of carbon atoms ranging from 16 to 36, notably ranging from 32 to 36, in particular 34, incorporating at least one carbocycle group, preferably one or two carbocycle(s), and more preferentially a central carbocycle group, in particular of mono- or polycyclic cycloalkyl type, notably cyclohexyl or decalinyl, in particular cyclohexyl.

In a particular embodiment, the polyacid(s) may be chosen from diacids of the fatty acid dimer type, containing a cycloalkyl group, in particular cyclohexyl, connected to the -C(O)OH groups via C2 to C10, in particular C4 to C8, notably C6, alkylene chains, said cycloalkyl group notably bearing C4 to C12, in particular C7 to C9, notably C8, alkyl side groups. In particular, the fatty acid dimer may be formed from C16 to C20, in particular C18 fatty acids, for example from oleic acid and/or linoleic acid. The fatty acid dimers may be commercially available. By way of example, mention may be made of the fatty acid dimers sold by the company Croda under the reference Pripol®, notably the cosmetic-grade Pripol® 1009. According to a particular embodiment, the polyacid(s) may comprise, or even constitute, fatty acid dimer diacid(s), for example Pripol® 1009.

Monoacids F

According to a particular embodiment, the compound(s) E are obtained from one or more monocarboxylic acids, also referred to in the text hereinbelow as “monoacids”, i.e. comprising a single carboxyl group.

Preferably, the monoacid(s) are acyclic or (poly)cyclic, saturated or unsaturated, aromatic or non-aromatic, linear or branched, and comprise a total number of carbon atoms (carbon atoms of the carboxyl group included) ranging from 6 to 32, in particular from 8 to 28 and more particularly from 10 to 20 carbon atoms.

According to a preferred embodiment, the monoacid(s) are non-aromatic, saturated or unsaturated, linear or branched, cyclic or non-cyclic, and comprise a total number of carbon atoms (carbon atoms of the carboxyl group included) ranging from 6 to 32, in particular from 8 to 30 carbon atoms and more particularly from 10 to 28 carbon atoms, preferentially from 12 to 26 carbon atoms, more preferentially from 16 to 24 carbon atoms, even more preferentially from 18 to 22 carbon atoms.

When the monoacid(s) used are of natural origin, they may notably constitute mixtures comprising saturated acids and unsaturated acids with conjugated and/or non-conjugated unsaturations.

According to a particular embodiment, the monoacid(s) are chosen from saturated or unsaturated fatty acids.

According to a first variant, the monoacid(s) are chosen from monocarboxylic acids comprising a linear or branched, preferably linear, saturated or unsaturated hydrocarbon-based chain comprising a total number of carbon atoms (carbon atoms of the carboxyl group included) of more than 7, in particular more than 8, more particularly ranging from 8 to 30, notably ranging from 14 to 26, even more particularly ranging from 16 to 22, preferably ranging from 18 to 20.

By way of example, the monoacid(s) may be chosen from isostearic acid (saturated branched C18), stearic acid (saturated linear C18), linoleic acid (polyunsaturated linear C18), arachidic acid (saturated linear C20), behenic acid (saturated linear C22), capric acid (saturated linear C10), caprylic acid (saturated linear C8), salts thereof with organic or mineral bases, isomers thereof, solvates thereof such as hydrates and mixtures thereof, preferably isostearic acid (saturated branched C18), capric acid (saturated linear C10), caprylic acid (saturated linear C8), salts thereof with organic or mineral bases, isomers thereof, solvates thereof such as hydrates and mixtures thereof.

According to another variant, the monoacid(s) are chosen from (poly)cyclic, preferably polycyclic monocarboxylic acids, comprising in particular a fused, saturated and/or unsaturated, preferably unsaturated, in particular non-aromatic, mono-, bi- or tricyclic carbocycle, and including from 5 to 20 carbon atoms, said carbocycle being optionally substituted with one or more (C₁-C₄)alkyl groups such as methyl.

Carboxylic acid anhydrides

According to a particular embodiment, the compound(s) E are obtained from one or more carboxylic acid anhydrides.

The term “carboxylic acid anhydride” means an organic compound resulting from the dehydration of a carboxylic acid and comprising at least one –C(O)-O-C(O)– functional group.

By way of example, the acid anhydride(s) may be chosen from trimellitic anhydride, phthalic anhydride, terephthalic anhydride and mixtures thereof.

Hydroxy acids

According to a particular embodiment, the compound(s) E are derived from the polycondensation of one or more hydroxy acids.

The term “hydroxy acid” means a monoacid or polyacid comprising a hydrocarbon-based chain substituted with at least one hydroxyl group.

The hydroxy acid(s) may be acyclic or (poly)cyclic, saturated or unsaturated, aromatic or non-aromatic, linear or branched, and comprise a total number of carbon atoms ranging from 4 to 32, in particular from 4 to 28 and more particularly from 4 to 22 carbon atoms.

For example, the hydroxy acid(s) may be chosen from hydroxystearic acids, hydroxybutyric acids, hydroxypentanoic acids, hydroxyhexanoic acids, lactic acid, ricinoleic acid, salts thereof with organic or mineral bases, isomers thereof, solvates thereof such as hydrates and mixtures thereof.

As examples of compounds E resulting from the polycondensation of one or more hydroxy acids, mention may be made of the compounds having the following INCI names: Polyhydroxybutyrate, Polyhydroxystearic Acid, Polylactic Acid, 3-Hydroxybutyrate/3-Hydroxyhexanoate Copolymer and Hydroxybutyric Acid/Hydroxypentanoic Acid Copolymer.

Lactones

According to a particular embodiment, the compound(s) E are derived from the ring-opening polymerization of one or more lactones.

The term “lactone” means an organic compound in which the –C(O)-O– functional group is part of a ring.

By way of example, the lactone(s) are chosen from ε-caprolactone, gluconolactones, glucarolactones, butyrolactones, valerolactones, octalactones, galactonolactones, and mixtures thereof; preferably, the lactone is ε-caprolactone.

By way of example, compound E is derived from ring-opening polymerization of one or more lactones: mention may be made of polycaprolactone.

It is understood that the particular modes of production of the compound(s) E described previously may be combined.

Particular embodiments

According to a particular embodiment, the compound(s) E are obtained by reacting one or more polyols as defined previously with one or more compounds chosen from the monoacids F as defined previously, the polyacids F as defined previously, the carboxylic acid anhydrides as defined previously, and mixtures thereof.

According to a more particular embodiment, the compound(s) E are derived from the reaction of one or more polyols as defined previously and one or more compounds chosen from the monoacids F as defined previously, the polyacids F as defined previously and mixtures thereof.

According to a variant, the compound(s) E are derived from the reaction of one or more polyols as defined previously and one or more monoacids F as defined previously, notably a plant oil notably chosen from triglycerides.

According to another variant, the compound(s) E are derived from the reaction of one or more polyols as defined previously and one or more diacids F as defined previously.

Thus, according to this latter variant, the compound(s) E can be derived from the reaction of one or more diols comprising a C2-C10, preferably C2-C8, more preferentially C2-C6 hydrocarbon-based chain, the hydrocarbon-based chain possibly being interrupted with an oxygen atom, preferably chosen from propanediols, butanediols, hexanediols, diethylene glycol, neopentyl glycol and mixtures thereof and one or more diacids F comprising a total number of carbon atoms (including carboxyl group carbon atoms) ranging from 2 to 54, notably from 2 to 50 and more particularly from 3 to 40, and even more particularly from 3 to 36.

More particularly, the compound(s) E are derived from the reaction of one or more dimers and/or trimers of saturated or unsaturated fatty acids, preferably unsaturated fatty acids and one or more diols.

In a preferred embodiment, the saturated fatty acid dimer(s) may comprise from 28 to 44 carbon atoms and two carboxylic acid groups. The saturated fatty acid trimer(s) may comprise from 42 to 66 carbon atoms and three carboxylic acid functions.

Preferably, one or more unsaturated fatty acid dimers are used, in particular containing 36 carbon atoms and two carboxylic acid groups.

The unsaturated fatty acid trimer(s) may comprise from three to six conjugated or non-conjugated unsaturations in their carbon chain.

Preferably, the unsaturated fatty acid dimer(s) and/or trimer(s) are polycarboxylic acids comprising at least two and up to six carboxylic acid groups per molecule. In a preferred embodiment, the unsaturated fatty acid dimer(s) may comprise from 28 to 44 carbon atoms and two carboxylic acid groups. The unsaturated fatty acid trimer(s) may comprise from 42 to 66 carbon atoms and three carboxylic acid functions.

Preferably, one or more unsaturated fatty acid dimers are used, in particular containing 36 carbon atoms and two carboxylic acid groups. Mixtures of dimers and trimers of unsaturated fatty acids and/or unsaturated fatty acids (unpolymerized and thus corresponding to a monomer) may also be used in the context of the invention. In the case of such a mixture, a mixture comprising more than 50% by weight of dimers is preferred, for example a mixture comprising more than 90% by weight, preferably more than 95%, of acids in dimer form, the remainder of the mixture being unsaturated fatty acid trimers and/or monomers. The unsaturated fatty acid dimer(s) and/or trimer(s) may optionally be hydrogenated after the unsaturated fatty acid polymerization reaction, notably to improve the stability of the dimer or trimer product. Hydrogenated fatty acid dimers (oleic or linoleic acid) are notably sold under the brand names Empol 1008, Empol 1004, Empol 1025, Empol 1011 and Empol 1062 by BASF, and Pripol 1006 (dilinoleic acid) by Uniqema, International. Uniqema also markets a hydrogenated fatty acid dimer under the name Pripol 1013 (hydrogenated dilinoleic acid).

The unsaturated fatty acid dimer is particularly preferably a linoleic acid dimer, also known as dilinoleic acid, obtained by intermolecular polymerization of linoleic acid. The unsaturated fatty acid may be of natural origin, preferably of plant origin. A fatty acid of plant origin may originate from any plant source that produces said fatty acid. For example, in the case of linoleic acid, use may be made of molecules extracted from soybean or from rapeseed.

According to another variant, the compound(s) E are derived from the reaction of one or more polyols as defined previously and one or more diacids F as defined previously and one or more monoacids F as defined previously.

Thus, according to this variant, the compound(s) E may be formed at least, or even formed solely, from glycerol, a fatty acid dimer as described previously, in particular of C34 to C38 and more particularly C36, for example the cosmetic-grade product sold by the company Croda under the reference Pripol® 1009, and isostearic acid.

Alternatively, according to this variant, the compound(s) E may be formed at least, or even formed solely, from pentaerythritol, at least one diacid F, preferably at least one diacid F with a molecular mass MM of less than or equal to 200 g. mol^-1, and more particularly chosen from oxalic acid, succinic acid, adipic acid, and mixtures thereof, and also the optical and geometrical isomers thereof, the salts thereof with organic or inorganic bases, and the solvates thereof such as hydrates, even more preferentially adipic acid; and at least one monoacid F as defined previously, preferably comprising more than 7 carbon atoms, in particular from 7 to 26 carbon atoms and more particularly from 7 to 20 carbon atoms, and more particularly a mixture of several monoacids of 7 to 26 carbon atoms such as a mixture of capric acid, caprylic acid and isostearic acid.

The compound(s) E used according to the invention may have a weight-average molar mass, Mw, ranging from 400 to 100 000 g.mol^-1. The weight-average molar mass may be determined by size exclusion chromatography (SEC).

According to another variant, the compound(s) E result from the reaction of one or more polyols as defined previously and one or more diacids F as defined previously and one or more carboxylic acid anhydrides as defined previously.

Thus, according to this last variant, the compound(s) E may be formed from neopentyl glycol and adipic acid and trimellitic anhydride.

According to a particular embodiment of the invention, the compound(s) E are liquid. The term “liquid compound” means a compound which begins to flow under its own weight in less than one minute at room temperature (25°C) and at atmospheric pressure.

The compound(s) E are more preferentially derived from:
- the reaction of one or more polyols as defined previously and one or more monoacids F as defined previously, notably a plant oil notably chosen from triglycerides; and/or
- the reaction of one or more polyols as defined previously and one or more diacids F as defined previously; and/or
- the reaction of one or more polyols as defined previously and one or more diacids F as defined previously and one or more monoacids F as defined previously; and/or
- the reaction of one or more polyols as defined previously and one or more diacids F as defined previously and one or more carboxylic acid anhydrides as defined previously; and/or
- polycondensation of one or more hydroxy acids; and/or
- ring-opening polymerization of one or more lactones;
it being understood that:
▪ the polyol(s) are preferably chosen from:
- diols and triols, such as propanediols, butanediols such as 1,4-butanediol, hexanediols, dilinoleic dimer alcohols, glycerol, diethylene glycol, neopentyl glycol, tricyclodecanedimethanol, trihydroxystearin, or 2-(dihydroxymethyl)butan-1-ol;
- tetraols such as pentaerythritol (tetramethylolmethane), erythritol or diglycerol;
- pentols such as xylitol;
- hexols such as sorbitol and mannitol, or dipentaerythritol;
- polyglycerol-3, polyglycerol-6 or polyglycerol-10; and
- mixtures thereof; and/or
▪ the monoacid(s) F are preferably chosen from monocarboxylic acids comprising a linear or branched, preferably linear, saturated or unsaturated hydrocarbon-based chain comprising a total number of carbon atoms (including carboxyl group carbon atoms) of more than 7, preferably more than 8, more preferentially from 8 to 30, the monoacid(s) F being even more preferentially chosen from capric acid, caprylic acid, isostearic acid, salts thereof with organic or mineral bases, isomers thereof and mixtures thereof; and/or
▪ the diacid(s) F are preferably chosen from dilinoleic acid, adipic acid, terephthalic acid, phthalic acid, sebacic acid, succinic acid, fumaric acid, salts thereof with organic or mineral bases, isomers thereof and mixtures thereof; and/or
▪ the hydroxy acid(s) are preferably chosen from hydroxystearic acids, hydroxybutyric acids, hydroxypentanoic acids, hydroxyhexanoic acids, lactic acid, salts thereof with organic or mineral bases, isomers thereof, solvates thereof such as hydrates and mixtures thereof; and/or
▪ the lactone(s) are preferably chosen from ε-caprolactone, gluconolactones, glucarolactones, butyrolactones, valerolactones, octalactones, galactonolactones, and mixtures thereof; more preferentially, the lactone is ε-caprolactone.

According to a preferred embodiment, the compound(s) E are chosen from the polymers having the following INCI names:
- Dimer Dilinoleyl Dimer Dilinoleate;
- Dilinoleic Acid/Butanediol Copolymer;
- Polyhydroxystearic Acid;
- Hydroxybutyric Acid /Hydroxypentanoic Acid Copolymer;
- 3-Hydroxybutyrate/3-Hydroxyhexanoate Copolymer;
- Polyhydroxybutyrate;
- Adipic Acid/Diglycol Crosspolymer;
- Adipic Acid/Neopentyl Glycol/Trimellitic Anhydride Copolymer;
- Polyethylene Terephthalate;
- Polybutylene Terephthalate;
- Polylactic Acid;
- Polycaprolactone;
- Dilinoleic Acid Propanediol Copolymer;
- Adipic Acid/Neopentyl Glycol Copolymer;
- Pentaerythrityl Isostearate/Caprate/Caprylate/Adipate;
- Diisostearoyl Polyglyceryl-3 Dimer Dilinoleate;
- Capryloyl Glycerin/Sebacic Acid Copolymer;
- 1,4-Butanediol/Succinic Acid/Adipic Acid Copolymer;
- 1,4-Butanediol/Succinic Acid/Adipic Acid/HDI Copolymer;
- Adipic Acid/1,4-Butanediol/Terephthalate Copolymer;
- Adipic Acid/Dilinoleic Acid/Hexylene Glycol Copolymer;
- Adipic Acid/Fumaric Acid/Phthalic Acid/Tricyclodecane Dimethanol Copolymer; and
- mixtures thereof.

According to a more preferred embodiment, the compound(s) E are chosen from the polymers having the following INCI names:
- Dimer Dilinoleyl Dimer Dilinoleate;
- Dilinoleic Acid/Butanediol Copolymer;
- Polyhydroxystearic acid; and
- mixtures thereof.

According to a preferred embodiment:
● compound A is caprylic acid and compound B is menthol, the mole ratio of the total amount of caprylic acid to the total amount of menthol in composition (C) preferably being less than or equal to 1, more preferentially equal to 1/2 or 1, even more preferentially equal to 1; and
● the compound(s) E are chosen from the polymers having the following INCI names:
- Dimer Dilinoleyl Dimer Dilinoleate;
- Dilinoleic Acid/Butanediol Copolymer;
- Polyhydroxystearic acid; and
- mixtures thereof.

Preferably, composition (C) comprises a total content of compounds E of at least 0.01% by weight, preferably at least 0.1% by weight, more preferentially ranging from 0.01% to 20% by weight, even more preferentially ranging from 0.1% to 15% by weight, relative to the total weight of composition (C).

Preferably, composition (C) comprises a total content of compounds A, B and E of at least 0.03% by weight, preferably at least 0.1% by weight, more preferentially at least 0.5% by weight, even more preferentially at least 1% by weight, most preferentially at least 2% by weight, better still at least 3% by weight, and even better still at least 4% by weight relative to the total weight of composition (C).

Preferably, composition (C) comprises a total content of compounds A, B and E of less than or equal to 100% by weight, preferably less than or equal to 99% by weight, more preferentially less than or equal to 95% by weight, relative to the total weight of composition (C).

According to a preferred embodiment, composition (C) comprises a total content of compounds A, B and E ranging from 0.03% to 100% by weight, preferably ranging from 0.1% to 100% by weight, more preferentially ranging from 0.5% to 100% by weight, even more preferentially ranging from 1% to 100% by weight, most preferentially ranging from 2% to 100% by weight, better still ranging from 3% to 100% by weight and even better still ranging from 4% to 100% by weight.

Preferably, the mass ratio of the total amount of compounds A and B to the total amount of compounds E in composition (C) is from 5 to 1000, preferably from 5 to 200.

Composition (C) may also comprise d) one or more pigments.

The term “pigment” refers to any pigment that gives colour to keratin materials. Their solubility in water at 25°C and at atmospheric pressure (760 mmHg) is less than 0.05% by weight, and preferably less than 0.01%.

The pigments that may be used are notably chosen from the organic and/or mineral pigments known in the art, notably those described in Kirk-Othmer’s Encyclopedia of Chemical Technology and in Ullmann’s Encyclopedia of Industrial Chemistry.

They may be natural, of natural origin, or non-natural.

These pigments may be in pigment powder or paste form. They may be coated or uncoated.

The pigments may be chosen, for example, from mineral pigments, organic pigments, lakes, pigments with special effects such as nacres or glitter flakes, and mixtures thereof.

The pigment may be a mineral pigment. The term “mineral pigment” refers to any pigment that satisfies the definition in Ullmann’s encyclopaedia in the chapter on inorganic pigments. Among the mineral pigments that are useful in the present invention, mention may be made of iron oxides, chromium oxides, manganese violet, ultramarine blue, chromium hydrate, ferric blue and titanium oxide.

The pigment may be an organic pigment. The term “organic pigment” refers to any pigment that satisfies the definition in Ullmann’s encyclopedia in the chapter on organic pigments.

The organic pigment may notably be chosen from nitroso, nitro, azo, xanthene, pyrene, quinoline, anthraquinone, triphenylmethane, fluoran, phthalocyanine, metal-complex, isoindolinone, isoindoline, quinacridone, perinone, perylene, diketopyrrolopyrrole, indigo, thioindigo, dioxazine, triphenylmethane and quinophthalone compounds.

In particular, the white or coloured organic pigments may be chosen from carmine, carbon black, aniline black, azo yellow, quinacridone, phthalocyanine blue, the blue pigments codified in the Color Index under the references CI 42090, 69800, 69825, 74100, 74160, the yellow pigments codified in the Color Index under the references CI 11680, 11710, 19140, 20040, 21100, 21108, 47000, 47005, the green pigments codified in the Color Index under the references CI 61565, 61570, 74260, the orange pigments codified in the Color Index under the references CI 11725, 45370, 71105, the red pigments codified in the Color Index under the references CI 12085, 12120, 12370, 12420, 12490, 14700, 15525, 15580, 15620, 15630, 15800, 15850, 15865, 15880, 26100, 45380, 45410, 58000, 73360, 73915, 75470, the pigments obtained by oxidative polymerization of indole or phenol derivatives as described in patent FR 2 679 771.

Examples that may also be mentioned include pigment pastes of organic pigments, such as the products sold by the company Hoechst under the names:
- Cosmenyl Yellow 10G: Yellow 3 pigment (CI 11710);
- Cosmenyl Yellow G: Yellow 1 pigment (CI 11680);
- Cosmenyl Orange GR: Orange 43 pigment (CI 71105);
- Cosmenyl Red R: Red 4 pigment (CI 12085);
- Cosmenyl Carmine FB: Red 5 pigment (CI 12490);
- Cosmenyl Violet RL: Violet 23 pigment (CI 51319);
- Cosmenyl Blue A2R: Blue 15.1 pigment (CI 74160);
- Cosmenyl Green GG: Green 7 pigment (CI 74260);
- Cosmenyl Black R: Black 7 pigment (CI 77266).

The pigments in accordance with the invention may also be in the form of composite pigments, as described in patent EP 1 184 426. These composite pigments may notably be composed of particles including an inorganic core, at least one binder for attaching the organic pigments to the core, and at least one organic pigment which at least partially covers the core.

The organic pigment may also be a lake. The term “lake” refers to dyes adsorbed onto insoluble particles, the assembly thus obtained remaining insoluble during use.

The inorganic substrates onto which the dyes are adsorbed are, for example, alumina, silica, calcium sodium borosilicate or calcium aluminium borosilicate, and aluminium.

Among the dyes, mention may be made of carminic acid. Mention may also be made of the dyes known under the following names: D&C Red 21 (CI 45 380), D&C Orange 5 (CI 45 370), D&C Red 27 (CI 45 410), D&C Orange 10 (CI 45 425), D&C Red 3 (CI 45 430), D&C Red 4 (CI 15 510), D&C Red 33 (CI 17 200), D&C Yellow 5 (CI 19 140), D&C Yellow 6 (CI 15 985), D&C Green (CI 61 570), D&C Yellow 10 (CI 77 002), D&C Green 3 (CI 42 053), D&C Blue 1 (CI 42 090).

An example of a lake that may be mentioned is the product known under the following name: D&C Red 7 (CI 15 850:1).

The pigment may also be a pigment with special effects. The term “pigments with special effects” means pigments that generally create a coloured appearance (characterized by a certain shade, a certain vivacity and a certain level of luminance) that is non-uniform and that changes as a function of the conditions of observation (light, temperature, angles of observation, etc.). They thereby differ from coloured pigments, which afford a standard uniform opaque, semi-transparent or transparent shade.

Several types of pigments with special effects exist: those with a low refractive index, such as fluorescent or photochromic pigments, and those with a higher refractive index, such as nacres, interference pigments or glitter flakes.

Examples of pigments with special effects that may be mentioned include nacreous pigments such as mica coated with titanium or with bismuth oxychloride, coloured nacreous pigments such as mica covered with titanium and with iron oxides, mica covered with iron oxide, mica covered with titanium and notably with ferric blue or with chromium oxide, mica covered with titanium and with an organic pigment as defined previously, and also nacreous pigments based on bismuth oxychloride. Nacreous pigments that may be mentioned include the nacres Cellini sold by BASF (mica-TiO₂-lake), Prestige sold by Eckart (mica-TiO₂), Prestige Bronze sold by Eckart (mica-Fe₂O₃) and Colorona sold by Merck (mica-TiO₂-Fe₂O₃).

Mention may also be made of the gold-coloured nacres sold notably by the company BASF under the name Brilliant Gold 212G (Timica), Gold 222C (Cloisonne), Sparkle Gold (Timica), Gold 4504 (Chromalite) and Monarch Gold 233X (Cloisonne); the bronze nacres sold notably by the company Merck under the name Bronze Fine (17384) (Colorona) and Bronze (17353) (Colorona) and by the company BASF under the name Super Bronze (Cloisonne); the orange nacres sold notably by the company BASF under the name Orange 363C (Cloisonne) and Orange MCR 101 (Cosmica) and by the company Merck under the name Passion Orange (Colorona) and Matte Orange (17449) (Microna); the brown nacres sold notably by the company BASF under the name Nu-antique Copper 340XB (Cloisonne) and Brown CL4509 (Chromalite); the nacres with a copper tint sold notably by the company BASF under the name Copper 340A (Timica); the nacres with a red tint sold notably by the company Merck under the name Sienna Fine (17386) (Colorona); the nacres with a yellow tint sold notably by the company BASF under the name Yellow (4502) (Chromalite); the red nacres with a gold tint sold notably by the company BASF under the name Sunstone G012 (Gemtone); the pink nacres sold notably by the company BASF under the name Tan Opale G005 (Gemtone); the black nacres with a gold tint sold notably by the company BASF under the name Nu-antique Bronze 240 AB (Timica), the blue nacres sold notably by the company Merck under the name Matte Blue (17433) (Microna), the white nacres with a silvery tint sold notably by the company Merck under the name Xirona Silver, and the golden-green pink-orange nacres sold notably by the company Merck under the name Indian Summer (Xirona), and mixtures thereof.

Still as examples of nacres, mention may also be made of particles including a borosilicate substrate coated with titanium oxide.

Particles comprising a glass substrate coated with titanium oxide are notably sold under the name Metashine MC1080RY by the company Toyal.

Finally, examples of nacres that may also be mentioned include polyethylene terephthalate glitter flakes, notably those sold by the company Meadowbrook Inventions under the name Silver 1P 0.004X0.004 (silver glitter flakes). It is also possible to envisage multilayer pigments based on synthetic substrates, such as alumina, silica, calcium sodium borosilicate, calcium aluminium borosilicate and aluminium.

The pigments with special effects may also be chosen from reflective particles, i.e. notably from particles whose size, structure, notably the thickness of the layer(s) of which they are made and their physical and chemical nature, and surface state, allow them to reflect incident light. This reflection may, where appropriate, have an intensity sufficient to create at the surface of the composition or of the mixture, when it is applied to the support to be made up, highlight points that are visible to the naked eye, i.e. more luminous points that contrast with their environment making them appear to sparkle.

The reflective particles may be selected so as not to significantly alter the colouring effect generated by the colouring agents with which they are combined, and more particularly so as to optimize this effect in terms of colour rendition. They may more particularly have a yellow, pink, red, bronze, orange, brown, gold and/or coppery colour or tint.

These particles may have varied forms and may notably be in platelet or globular form, in particular in spherical form.

The reflective particles, whatever their form, may or may not have a multilayer structure and, in the case of a multilayer structure, may have, for example, at least one layer of uniform thickness, notably of a reflective material.

When the reflective particles do not have a multilayer structure, they may be composed, for example, of metal oxides, notably titanium or iron oxides obtained synthetically.

When the reflective particles have a multilayer structure, they may include, for example, a natural or synthetic substrate, notably a synthetic substrate at least partially coated with at least one layer of a reflective material, notably of at least one metal or metallic material. The substrate may be made of one or more organic and/or mineral materials.

More particularly, it may be chosen from glasses, ceramics, graphite, metal oxides, aluminas, silicas, silicates, notably aluminosilicates and borosilicates, and synthetic mica, and mixtures thereof, this list not being limiting.

The reflective material may include a layer of metal or of a metallic material.

Reflective particles are notably described in JP-A-09188830, JP-A-10158450, JP-A-10158541, JP-A-07258460 and JP-A-05017710.

Again as an example of reflective particles including a mineral substrate coated with a layer of metal, mention may also be made of particles including a silver-coated borosilicate substrate.

Particles with a silver-coated glass substrate, in the form of platelets, are sold under the name Microglass Metashine REFSX 2025 PS by the company Toyal. Particles with a glass substrate coated with a nickel/chromium/molybdenum alloy are sold under the names Crystal Star GF 550 and GF 2525 by this same company.

Use may also be made of particles comprising a metal substrate, such as silver, aluminium, iron, chromium, nickel, molybdenum, gold, copper, zinc, tin, magnesium, steel, bronze or titanium, said substrate being coated with at least one layer of at least one metal oxide, such as titanium oxide, aluminium oxide, iron oxide, cerium oxide, chromium oxide, silicon oxides and mixtures thereof.

Examples that may be mentioned include aluminium powder, bronze powder or copper powder coated with SiO₂ sold under the name Visionaire by the company Eckart.

Mention may also be made of interference pigments which are not attached to a substrate, such as liquid crystals (Helicones HC from Wacker) or interference holographic glitter flakes (Geometric Pigments or Spectra f/x from Spectratek). Special-effect pigments also comprise fluorescent pigments, whether these are substances that are fluorescent in daylight or that produce an ultraviolet fluorescence, phosphorescent pigments, photochromic pigments, thermochromic pigments and quantum dots, sold, for example, by the company Quantum Dots Corporation.

The variety of pigments that may be used in the present invention makes it possible to obtain a wide range of colours, and also particular optical effects such as metallic effects or interference effects.

The size of the pigment used in the composition according to the present invention is generally between 10 nm and 200 µm, preferably between 20 nm and 80 µm and more preferentially between 30 nm and 50 µm.

The pigments may be dispersed in the composition by means of a dispersant.

The dispersant serves to protect the dispersed particles against agglomeration or flocculation thereof. This dispersant may be a surfactant, an oligomer, a polymer or a mixture of several thereof, bearing one or more functionalities with strong affinity for the surface of the particles to be dispersed. In particular, they may become physically or chemically attached to the surface of the pigments. These dispersants also contain at least one functional group that is compatible with or soluble in the continuous medium. In particular, esters of 12-hydroxystearic acid in particular and of C8 to C20 fatty acid and of polyols such as glycerol or diglycerol are used, such as poly(12-hydroxystearic acid) stearate with a molecular weight of approximately 750 g/mol, such as the product sold under the name Solsperse 21 000 by the company Avecia, polyglyceryl-2 dipolyhydroxystearate (CTFA name) sold under the reference Dehymyls PGPH by the company Henkel, or else polyhydroxystearic acid such as the product sold under the reference Arlacel P100 by the company Uniqema, and mixtures thereof.

As other dispersants that may be used in the compositions of the invention, mention may be made of quaternary ammonium derivatives of polycondensed fatty acids, for instance Solsperse 17 000 sold by the company Avecia, and polydimethylsiloxane/oxypropylene mixtures such as those sold by the company Dow Corning under the references DC2-5185 and DC2-5225 C.

The pigments used in the composition may be surface-treated with an organic agent.

Thus, the pigments surface-treated beforehand that are useful in the context of the invention are pigments which have been completely or partially subjected to a surface treatment of chemical, electronic, electrochemical, mechanochemical or mechanical nature with an organic agent, such as those described notably in Cosmetics and Toiletries, February 1990, Vol. 105, pages 53-64, before being dispersed in the composition in accordance with the invention. These organic agents may be chosen, for example, from waxes, for example carnauba wax and beeswax; fatty acids, fatty alcohols and derivatives thereof, such as stearic acid, hydroxystearic acid, stearyl alcohol, hydroxystearyl alcohol and lauric acid and derivatives thereof; anionic surfactants; lecithins; sodium, potassium, magnesium, iron, titanium, zinc or aluminium salts of fatty acids, for example aluminium stearate or laurate; metal alkoxides; polyethylene; (meth)acrylic polymers, for example polymethyl methacrylates; polymers and copolymers containing acrylate units; alkanolamines; silicone compounds, for example silicones, notably polydimethylsiloxanes; organofluorine compounds, for example perfluoroalkyl ethers; fluorosilicone compounds.

The surface-treated pigments that are useful in the composition may also have been treated with a mixture of these compounds and/or may have undergone several surface treatments.

The surface-treated pigments that are useful in the context of the present invention may be prepared according to surface-treatment techniques that are well known to those skilled in the art, or may be commercially available as is.

Preferably, the surface-treated pigments are coated with an organic layer.

The organic agent with which the pigments are treated may be deposited on the pigments by evaporation of solvent, chemical reaction between the molecules of the surface agent or creation of a covalent bond between the surface agent and the pigments.

The surface treatment may thus be performed, for example, by chemical reaction of a surface agent with the surface of the pigments and creation of a covalent bond between the surface agent and the pigments or the fillers. This method is notably described in patent US 4 578 266.

An organic agent covalently bonded to the pigments will preferably be used.

The agent for the surface treatment may represent from 0.1% to 50% by weight relative to the total weight of the surface-treated pigment, preferably from 0.5% to 30% by weight and even more preferentially from 1% to 20% by weight relative to the total weight of the surface-treated pigment.

Preferably, the surface treatments of the pigments are chosen from the following treatments:
- a PEG-silicone treatment, for instance the AQ surface treatment sold by LCW;
- a methicone treatment, for instance the SI surface treatment sold by LCW;
- a dimethicone treatment, for instance the Covasil 3.05 surface treatment sold by LCW;
- a dimethicone/trimethyl siloxysilicate treatment, for instance the Covasil 4.05 surface treatment sold by LCW;
- a magnesium myristate treatment, for instance the MM surface treatment sold by LCW;
- an aluminium dimyristate treatment, for instance the MI surface treatment sold by Miyoshi;
- a perfluoropolymethyl isopropyl ether treatment, for instance the FHC surface treatment sold by LCW;
- an isostearyl sebacate treatment, for instance the HS surface treatment sold by Miyoshi;
- a perfluoroalkyl phosphate treatment, for instance the PF surface treatment sold by Daito;
- an acrylate/dimethicone copolymer and perfluoroalkyl phosphate treatment, for instance the FSA surface treatment sold by Daito;
- a polymethylhydrogenosiloxane/perfluoroalkyl phosphate treatment, for instance the FS01 surface treatment sold by Daito;
- an acrylate copolymer/dimethicone treatment, for instance the ASC surface treatment sold by Daito;
- an isopropyl titanium triisostearate treatment, for instance the ITT surface treatment sold by Daito;
- an acrylate copolymer treatment, for instance the APD surface treatment sold by Daito;
- a perfluoroalkyl phosphate/isopropyl titanium triisostearate treatment, for instance the PF + ITT surface treatment sold by Daito.

According to a particular embodiment of the invention, the dispersant is present with organic or mineral pigments in submicron-sized particulate form.

The term “submicron-sized” or “submicronic” refers to pigments having a particle size that has been micronized by a micronization method and having a mean particle size of less than a micrometre (µm), in particular between 0.1 and 0.9 µm, and preferably between 0.2 and 0.6 µm.

According to one embodiment, the dispersant and the pigment(s) are present in an amount (dispersant:pigment), according to a weight ratio, of between 1:4 and 4:1, particularly between 1.5:3.5 and 3.5:1 or better still between 1.75:3 and 3:1.

The dispersant(s) may therefore have a silicone backbone, such as silicone polyether and dispersants of amino silicone type. Among the suitable dispersants that may be mentioned are:
- amino silicones, i.e. silicones comprising one or more amine groups, such as those sold under the following names and references: BYK LPX 21879, par BYK, GP-4, GP-6, GP-344, GP-851, GP-965, GP-967 and GP-988-1, sold by Genesee Polymers,
- silicone acrylates such as Tego® RC 902, Tego® RC 922, Tego® RC 1041, and Tego® RC 1043, sold by Evonik,
- polydimethylsiloxane (PDMS) silicones having carboxyl groups, such as X-22162 and X-22370, sold by Shin-Etsu, epoxy silicones, such as GP-29, GP-32, GP-502, GP-504, GP-514, GP-607, GP-682 and GP-695, sold by Genesee Polymers, or Tego® RC 1401, Tego® RC 1403 and Tego® RC 1412, sold by Evonik.

According to a particular embodiment, the dispersant(s) are of amino silicone type and are cationic.

Preferably, the pigment(s) are chosen from mineral pigments, mixed mineral-organic pigments or organic pigments.

In one variant of the invention, the pigment(s) are organic pigments, preferentially organic pigments surface-treated with an organic agent chosen from silicone compounds. In another variant of the invention, the pigment(s) are mineral pigments.

Preferably, the pigment(s) used in the process of the invention are chosen from nacres, carbon blacks, such as Black 2, iron oxides, notably red, brown or black iron oxides, and micas coated with iron oxide, triarylmethane pigments, notably blue and violet triarylmethane pigments, such as Blue 1 Lake, azo pigments, notably red azo pigments, such as D&C Red 7, alkali metal or alkaline-earth metal salts of lithol red, such as the calcium salt of lithol red B, and mixtures thereof.

More preferentially, the pigment(s) are chosen from iron oxides, notably red, brown or black iron oxides.

Even more preferentially, the pigment(s) are chosen from red iron oxides.

As an example of a red iron oxide, mention may be made of the iron oxide sold by the company Sun Chemical under the name SunPuro® Red Iron Oxide.

Composition (C) may comprise a total content of pigments ranging from 0.001% to 20% by weight, preferably ranging from 0.005% to 15% by weight, more preferentially ranging from 0.05% to 10% by weight, relative to the total weight of composition (C).

Other features of composition (C)

Composition (C) is a cosmetic composition, i.e. a composition which comprises a cosmetically acceptable medium, i.e. a medium that is compatible with human keratin fibres.

Composition (C) may comprise water, preferably in a total content ranging from 0.1% to 98% by weight, relative to the total weight of the composition.

According to a preferred embodiment, composition (C) comprises a total water content of less than 30% by weight, preferably less than 10% by weight, more preferentially less than 5% by weight, even more preferentially less than 1% by weight, most preferentially less than 0.1% by weight, and better still less than 0.01% by weight relative to the total weight of composition (C), and even better still composition (C) is anhydrous.

Where appropriate, such small amounts of water may notably be introduced by ingredients of the composition that may contain residual amounts thereof.

The pH of composition (C) is preferably from 2 to 11, more preferentially from 3 to 10.5. The pH can be adjusted using an organic or mineral acid or an organic or mineral base normally used in cosmetics.

Composition (C) may comprise one or more organic solvents chosen from C₂-C₄ alcohols, polyols and polyol ethers, aromatic alcohols, hydrocarbon-based oils and mixtures thereof.

When present in composition (C), this or these organic solvents may be present in composition (C) in a total content ranging from 0.01% to 98% by weight, preferably ranging from 30% to 95% by weight relative to the total weight of composition (C).

Composition (C) is preferably liquid.

For the purposes of the present invention, the term “liquid composition” means, on a macroscopic scale, a composition which does not have its own shape and cannot be grasped, unlike a solid. It is a fluid which adapts to the shape of the container in which it is placed at room temperature (25°C). When poured into another container, a liquid retains its volume. A liquid thus has its own volume. At rest, the free surface of a liquid is generally flat and horizontal.

Composition (C) may be in any presentation form conventionally used for haircare application. In a non-limiting manner, composition (C) may be in the form of a lotion, serum, cream, mousse, gel, spray or lacquer.

Composition (C) may be used in a rinse-off or leave-on application.

Composition (C) may be in the form of a mask, a conditioning composition or a pre-shampoo. Composition (C) may also be in the form of a composition to be added to or mixed with a mask or a conditioning composition before application.

Composition (C) may be packaged in a pump bottle or in an aerosol container, so as to apply composition (C) in vapourized (lacquer) or foam form. In these cases, composition (C) preferably comprises at least one propellant.

According to a preferred embodiment, composition (C) comprises a total content of colouring agents of less than 0.1% by weight, preferably less than 0.01% by weight, more preferentially less than 0.001% by weight relative to the total weight of composition (C); even more preferentially, composition (C) is free of colouring agents.

The term “colouring agent” means an oxidation dye, a direct dye or a pigment.

The term “oxidation dye” means an oxidation dye precursor chosen from oxidation bases and couplers. Oxidation bases and couplers are colourless or sparingly coloured compounds, which, via a condensation reaction in the presence of an oxidizing agent, give a coloured species;

The term “direct dye” means a natural and/or synthetic dye, including in the form of an extract or extracts, other than oxidation dyes. These are coloured compounds that will spread superficially on the fibre. They may be ionic or nonionic, i.e. anionic, cationic, neutral or nonionic.

According to a preferred embodiment, composition (C) comprises a total silicone content of less than 5% by weight, preferably less than 2% by weight, more preferentially less than 1% by weight, even more preferentially less than 0.1% by weight, most preferentially less than 0.01% by weight, and better still less than 0.001% by weight relative to the total weight of composition (C), and even better still composition (C) is silicone-free.

According to a preferred embodiment, composition (C) comprises a total content of cationic polymers of less than 5% by weight, preferably less than 2% by weight, more preferentially less than 1% by weight, even more preferentially less than 0.1% by weight, most preferentially less than 0.01% by weight, and better still less than 0.001% by weight relative to the total weight of composition (C), and even better still composition (C) is free of cationic polymers.

The term “cationic polymer” means any non-silicone polymer (not comprising silicon atoms) containing cationic groups and/or groups that can be ionized into cationic groups, and not containing any anionic groups and/or groups that can be ionized into anionic groups.

According to a preferred embodiment, composition (C) comprises a total content of cationic surfactants of less than 5% by weight, preferably less than 2% by weight, more preferentially less than 1% by weight, even more preferentially less than 0.1% by weight, most preferentially less than 0.01% by weight, and better still less than 0.001% by weight relative to the total weight of composition (C), and even better still composition (C) is free of cationic surfactants.

According to a preferred embodiment, composition (C) comprises a total content of poly(oxyethylenated) compounds of less than 5% by weight, preferably of less than 2% by weight, more preferentially of less than 1% by weight, even more preferentially of less than 0.1% by weight, most preferentially of less than 0.01% by weight, and better still of less than 0.001% by weight relative to the total weight of composition (C), and even better still composition (C) is free of poly(oxyethylenated) compounds.

Examples of poly(oxyethylenated) compounds that may be mentioned include polyethylene glycols (PEGs).

Composition (C) may be applied to dry or wet keratin fibres, preferably wet keratin fibres.

The bath ratio of composition (C) applied to the keratin fibres may range from 0.02 to 10. The term “bath ratio” means the ratio between the total weight of composition (C) applied and the total weight of keratin fibres to be treated.

The process may comprise at least one additional step following step i), chosen from steps ii) to iv) below:
ii) a step of applying composition (C) to the keratin fibres, preferably for a period of at least 10 seconds, said application step optionally being performed under an airtight film of wrapper or plastic film type;
iii) a step of rinsing and/or washing the keratin fibres;
iv) a step of drying the keratin fibres in ambient air or with the aid of a heating device.

Preferably, the process comprises the additional steps ii) and iv) as described previously and performed in that order.

According to a particular embodiment, the process comprises all the additional steps ii), iii) and iv) as described previously and performed in that order.

The step of applying composition (C) may last from 10 seconds to 60 minutes, preferably from 30 seconds to 30 minutes.

The temperature of the heating device may range from 45°C to 230°C, preferably from 45°C to 100°C, more preferentially from 50°C to 80°C. A hairdryer, a heating hood, an iron or a heating brush may be used, for example, as heating device.

The drying step iv) may also be a combination of drying with air or with a heating device at a temperature ranging from 50°C to 80°C, such as a hairdryer or a heating hood, possibly followed by an ironing step, preferably with a straightening iron.

Steps i) and optionally steps ii) to iv) may be repeated as many times as required and each cycle of steps may be spaced from the next by a few minutes to a few days or weeks. Hair treatments different from the invention may be performed between different application cycles, before or after.

Composition (C)

Uses

Examples

The examples that follow will allow the invention to be understood more clearly, without, however, being limiting in nature. In the examples which follow, unless otherwise indicated, all the amounts are shown as mass percentages relative to the total weight of the composition.

The following compositions C1 to C3 were prepared according to the preparation protocol described hereinbelow:

Ingredients	C1	C2	C3
Polyhydroxystearic Acid (Dispersun DSP-OL300 sold by the company Innospec Performance Chemicals)	5	-	-
Dilinoleic Acid/Butanediol Copolymer (Viscoplast 14436 H sold by the company Biosynthis)	-	5	-
Dimer Dilinoleyl Dilinoleate (Lusplan DD-DA7 sold by the company Nippon Fine Chemical Company Ltd.)	-	-	5
Caprylic acid/menthol mixture (1/1 mole ratio)	qs 100	qs 100	qs 100

Process for preparing compositions C1 to C3

1 mol of caprylic acid is weighed out in a flask, into which 1 mol of menthol is added. The mixture is heated with stirring at 70°C for 1 hour. After the temperature of the reaction medium has returned to room temperature, compound E is added to the resulting liquid and the mixture is heated again with stirring at 70°C for 20 minutes. After returning to room temperature, the composition is obtained in the form of a colourless, transparent, slightly viscous, oily liquid.

Example 1: Evaluation of the “smooth feel” via the friction test

The surface of natural hair is perceived as smooth, i.e. with a low coefficient of friction, whereas the surface of damaged hair is perceived as rough, i.e. with a high coefficient of friction.

Hair treatments that damage the hair, such as dyeing and bleaching, are known to increase the hair’s coefficient of friction.

Consequently, the lower the coefficient of friction of the hair, the better the sensation of repaired hair and the ease with which the hair can be combed and disentangled under both dry and wet conditions.

The “smooth feel” was evaluated for compositions C2 and C3 according to the evaluation protocol described hereinbelow.

Locks used

For the study, 3.5 cm-long locks of bleached Caucasian type hair (alkaline solubility AS22) were used.

Evaluation protocol

In this test, the 3.5 cm-long lock is fixed in the specimen holder of a Zwickiline Z2.5 mechanical testing machine (Zwick, Germany) equipped with a 100 Newton (N) measuring cell. A normal force of 0.5 N is applied to the locks using forceps covered with disposable plastic foam. The foam is replaced after each measurement. The test machine applies a movement at a constant speed of 100 mm/min to extract the lock from the forceps. During removal, the force required to extract the lock of hair is measured as a function of the displacement. The force/displacement curve obtained is characterized by a plateau at the end of the stroke, and the average force at the plateau is recorded. The impact of the hair treatments on the friction properties is determined by comparing the average force at the plateau for reference locks with the average force at the plateau for treated locks.

For measurements in the dry state (dry friction force), the hair is conditioned at 25°C and 45% relative humidity.

For wet measurements (wet friction force), the hair locks are immersed in demineralized water for one minute before measurement.

Compositions C2 and C3 were applied according to the leave-on protocol described hereinbelow, then dry and wet measurements were taken according to the protocol described previously.

A force ratio between treated and untreated hair was thus determined: F_treated(N)/F_untreated(N).

Leave-on protocol

1) Washing of the lock with a DOP shampoo using a bath ratio of 0.4 g/g of hair;

2) Combing the lock;

3) Application of the compositions to the hair while still wet, in a bath ratio of 0.15 g/g of hair, no leave-on time;

4) Leaving the lock to dry at room temperature (22°C).

Results

The results of the measurements are summarized in the table below:

Composition tested	Protocol	F _treated /F _untreated on dry hair	F _treated /F _untreated on wet hair
C2	Leave-on	0.95	0.79
C3	Leave-on	0.88	0.70

Lower friction forces are observed on dry and wet hair for the hair treated via the process according to the present invention, compared to the untreated hair. The hair surface is smoother, even in the absence of silicone-based starting materials. The treated hair is softer and easier to comb and to disentangle, compared to the untreated hair.

Claims

Process for treating keratin fibres, comprising step i) of applying to the keratin fibres a composition (C) comprising:
a) one or more compounds A chosen from the compounds of formula (I) below, salts thereof, isomers thereof, solvates thereof such as hydrates and mixtures thereof:

in which formula (I):
▪ R¹ represents:
- a linear or branched, saturated or unsaturated hydrocarbon-based group comprising from 6 to 26 carbon atoms, the hydrocarbon-based group being optionally substituted with one or more identical or different groups chosen from: hydroxyl (-OH), amino (-NH₂), carboxyl (-COOH), (hetero)cyclic such as phenyl and/or optionally interrupted with one or more heteroatoms or groups chosen from -O-, -CO-, -NR^a-, or combinations thereof such as -O-CO-, -(CO)-O-, –NR^a-(CO)– or –(CO)-NR^a–; or
- a (hetero)cyclic group such as phenyl, optionally substituted with one or more identical or different groups chosen from: hydroxyl (-OH) or R^b-(CO)-;
▪ R^a represents a hydrogen atom or a linear or branched, saturated or unsaturated hydrocarbon-based group comprising from 1 to 10 carbon atoms optionally substituted with one or more identical or different groups chosen from (-OH), amino (-NH₂) or carboxyl (-COOH);
▪ R^b represents a (C₂-C₁₀)alkyl group; and
b) one or more compounds B chosen from oxygenated terpene compounds, preferably chosen from menthol, menthone, terpineol, isoborneol, camphor, nerol, citronellal, citronellol, myrcenol, linalool, geraniol, vitamin A, carvone, eugenol, thymol, fenchone, borneol, eucalyptol, cubebol, farnesol, patchoulol, viridiflorol, cafestol, ferruginol, isomers thereof, solvates thereof such as hydrates and mixtures thereof; and
c) one or more compounds E chosen from oligoesters, polyesters and mixtures thereof.
Process according to the preceding claim, in which at least one of the compounds A, preferably all of the compounds A, are present in composition (C) in non-salified form.
Process according to either of the preceding claims, in which the mole ratio of the total amount of compounds A to the total amount of compounds B present in composition (C) is less than or equal to 1, preferably ranging from 1 to 0.25.
Process according to any one of the preceding claims, in which R¹ represents a linear or branched, saturated or unsaturated hydrocarbon-based group comprising from 6 to 26 carbon atoms, the hydrocarbon-based group being optionally substituted with one or more identical or different groups chosen from: hydroxyl (-OH), amino (-NH₂), carboxyl (-COOH), (hetero)cyclic such as phenyl and/or optionally interrupted with one or more heteroatoms or groups chosen from -O-, -CO-, –NR^a–, or combinations thereof such as -O-CO-, -(CO)-O-, –NR^a-(CO)– or –(CO)-NR^a–, R^a being as defined in Claim 1, preferably an unsubstituted, saturated or unsaturated, linear or branched hydrocarbon-based group comprising from 6 to 26 carbon atoms, more preferentially an unsubstituted, saturated or unsaturated, linear or branched hydrocarbon-based group comprising from 6 to 20 carbon atoms, even more preferentially a (C₆-C₂₀)alkyl group, most preferentially a (C₆-C₁₂)alkyl group.
Process according to any one of the preceding claims, in which the compound(s) A are chosen from the following compounds 1 to 39, the salts thereof, the isomers thereof, and the solvates thereof such as hydrates, and mixtures thereof:

preferably chosen from compounds 1 to 20, 22, 25, 26, 28, 31, 32, 36 or 39, the salts thereof, the isomers thereof, and the solvates thereof such as hydrates, and mixtures thereof;
more preferentially chosen from compounds 14, 16 or 17, the salts thereof, the isomers thereof, and the solvates thereof such as hydrates, and mixtures thereof;
even more preferentially chosen from compounds 16 or 17, the salts thereof, the isomers thereof, and the solvates thereof such as hydrates, and mixtures thereof.
Process according to any one of the preceding claims, in which the compound(s) B are chosen from menthol, menthone, terpineol, isoborneol, camphor, nerol, citronellal, citronellol, myrcenol, linalool, geraniol, vitamin A, carvone, eugenol, thymol, fenchone, borneol, eucalyptol, isomers thereof, solvates thereof such as hydrates and mixtures thereof, preferably from menthol, thymol, isomers thereof, solvates thereof such as hydrates and mixtures thereof, more preferentially from menthol, isomers thereof, solvates thereof such as hydrates and mixtures thereof.
Process according to any one of the preceding claims, in which:
- compound A is capric acid and compound B is menthol, the mole ratio of the total amount of capric acid to the total amount of menthol in composition (C) preferably being less than or equal to 1, more preferentially equal to 1/2; or
- compound A is lauric acid and compound B is menthol, the mole ratio of the total amount of lauric acid to the total amount of menthol in composition (C) preferably being less than or equal to 1, more preferentially equal to 1/2; or
- compound A is caprylic acid and compound B is menthol, the mole ratio of the total amount of caprylic acid to the total amount of menthol in composition (C) preferably being less than or equal to 1, more preferentially equal to 1/2 or 1, even more preferentially equal to 1;
preferably:
- compound A is capric acid and compound B is menthol, the mole ratio of the total amount of capric acid to the total amount of menthol in composition (C) preferably being less than or equal to 1, more preferentially equal to 1/2; or
- compound A is caprylic acid and compound B is menthol, the mole ratio of the total amount of caprylic acid to the total amount of menthol in composition (C) preferably being less than or equal to 1, more preferentially equal to 1/2 or 1, even more preferentially equal to 1;
preferably, compound A is caprylic acid and compound B is menthol, the mole ratio of the total amount of caprylic acid to the total amount of menthol in composition (C) preferably being less than or equal to 1, more preferentially equal to 1/2 or 1, even more preferentially equal to 1.
Process according to any one of the preceding claims, in which composition (C) comprises:
- a total content of compounds A ranging from 0.01% to 99%, preferably ranging from 0.5% to 99% by weight, more preferentially ranging from 2% to 98% by weight, even more preferentially ranging from 2.5% to 80% by weight, relative to the total weight of composition (C); and/or
- a total content of compounds B ranging from 0.01% to 99% by weight, preferably ranging from 0.5% to 99% by weight, more preferentially ranging from 2% to 98% by weight and even more preferentially ranging from 2.5% to 80% by weight, relative to the total weight of composition (C).
Process according to any one of the preceding claims, in which composition (C) comprises a total content of compounds A and B ranging from 0.02% to 99.9% by weight, preferably ranging from 0.1% to 99% by weight, more preferentially ranging from 0.5% to 99% by weight, even more preferentially ranging from 1% to 99% by weight, most preferentially ranging from 2% to 99% by weight, better still ranging from 3% to 99% by weight, and even better still ranging from 4% to 99% by weight relative to the total weight of composition (C).
Process according to any one of the preceding claims, in which the compound(s) E are derived from:
- reaction of one or more polyols and one or more compounds chosen from carboxylic acids F comprising one or more carboxyl groups, carboxylic acid anhydrides and mixtures thereof; and/or
- polycondensation of one or more hydroxy acids; and/or
- ring-opening polymerization of one or more lactones.
Process according to any one of the preceding claims, in which the compound(s) E are derived from:
- the reaction of one or more polyols and one or more monoacids F, notably a plant oil notably chosen from triglycerides; and/or
- the reaction of one or more polyols and one or more diacids F; and/or
- the reaction of one or more polyols and one or more diacids F and one or more monoacids F; and/or
- the reaction of one or more polyols and one or more diacids F and one or more carboxylic acid anhydrides; and/or
- polycondensation of one or more hydroxy acids; and/or
- ring-opening polymerization of one or more lactones;
it being understood that:
▪ the polyol(s) are preferably chosen from:
- diols and triols, such as propanediols, butanediols such as 1,4-butanediol, hexanediols, dilinoleic dimer alcohols, glycerol, diethylene glycol, neopentyl glycol, tricyclodecanedimethanol, trihydroxystearin, or 2-(dihydroxymethyl)butan-1-ol;
- tetraols such as pentaerythritol (tetramethylolmethane), erythritol or diglycerol;
- pentols such as xylitol;
- hexols such as sorbitol, mannitol or dipentaerythritol;
- polyglycerol-3, polyglycerol-6 or polyglycerol-10; and
- and mixtures thereof; and/or
▪ the monoacid(s) F are preferably chosen from monocarboxylic acids comprising a linear or branched, preferably linear, saturated or unsaturated hydrocarbon-based chain comprising a total number of carbon atoms (including carboxyl group carbon atoms) of more than 7, preferably more than 8, more preferentially from 8 to 30, the monoacid(s) F being even more preferentially chosen from capric acid, caprylic acid, isostearic acid, salts thereof with organic or mineral bases, isomers thereof and mixtures thereof; and/or
▪ the diacid(s) F are preferably chosen from dilinoleic acid, adipic acid, terephthalic acid, phthalic acid, sebacic acid, succinic acid, fumaric acid, salts thereof with organic or mineral bases, isomers thereof and mixtures thereof; and/or
▪ the hydroxy acid(s) are preferably chosen from hydroxystearic acids, hydroxybutyric acids, hydroxypentanoic acids, hydroxyhexanoic acids, lactic acid, salts thereof with organic or mineral bases, isomers thereof, solvates thereof such as hydrates and mixtures thereof; and/or
▪ the lactone(s) are preferably chosen from ε-caprolactone, gluconolactones, glucarolactones, butyrolactones, valerolactones, octalactones, galactonolactones, and mixtures thereof; more preferentially, the lactone is ε-caprolactone;
the compound(s) E preferably being chosen from the polymers having the following INCI names:
- Dimer Dilinoleyl Dimer Dilinoleate;
- Dilinoleic Acid/Butanediol Copolymer;
- Polyhydroxystearic Acid;
- Hydroxybutyric Acid/Hydroxypentanoic Acid Copolymer;
- 3-Hydroxybutyrate/3-Hydroxyhexanoate Copolymer;
- Polyhydroxybutyrate;
- Adipic Acid/Diglycol Crosspolymer;
- Adipic Acid/Neopentyl Glycol/Trimellitic Anhydride Copolymer;
- Polyethylene Terephthalate;
- Polybutylene Terephthalate;
- Polylactic Acid;
- Polycaprolactone;
- Dilinoleic Acid Propanediol Copolymer;
- Adipic Acid/Neopentyl Glycol Copolymer;
- Pentaerythrityl Isostearate/Caprate/Adipate;
- Diisostearoyl Polyglyceryl-3 Dimer Dilinoleate;
- Capryloyl Glycerin/Sebacic Acid Copolymer;
- 1,4-Butanediol/Succinic Acid/Adipic Acid Copolymer;
- 1,4-Butanediol/Succinic Acid/Adipic Acid/HDI Copolymer;
- Adipic Acid/1,4-Butanediol/Terephthalate Copolymer;
- Adipic Acid/Dilinoleic Acid/Hexylene Glycol Copolymer;
- Adipic Acid/Fumaric Acid/Phthalic Acid/Tricyclodecane Dimethanol Copolymer; and
- mixtures thereof;
the compound(s) E more preferentially being chosen from the polymers having the following INCI names:
- Dimer Dilinoleyl Dimer Dilinoleate;
- Dilinoleic Acid/Butanediol Copolymer;
- Polyhydroxystearic acid; and
- mixtures thereof.
Process according to any one of the preceding claims, in which composition (C) comprises a total content of compounds E of at least 0.01% by weight, preferably at least 0.1% by weight, more preferentially ranging from 0.01% to 20% by weight, even more preferentially ranging from 0.1% to 15% by weight, relative to the total weight of composition (C).
Process according to any one of the preceding claims, in which the mass ratio of the total amount of compounds A and B to the total amount of compounds E in composition (C) is from 5 to 1000, preferably from 5 to 200.
Process according to any one of the preceding claims, in which composition (C) comprises a total content of silicones of less than 5% by weight, preferably less than 2% by weight, more preferentially less than 1% by weight, even more preferentially less than 0.1% by weight, most preferentially less than 0.01% by weight, and better still less than 0.001% by weight relative to the total weight of composition (C), and even better still composition (C) is free of silicones.
Process according to any one of the preceding claims, in which composition (C) comprises a total content of cationic polymers of less than 5% by weight, preferably less than 2% by weight, more preferentially less than 1% by weight, even more preferentially less than 0.1% by weight, most preferentially less than 0.01% by weight, and better still less than 0.001% by weight relative to the total weight of composition (C), and even better still composition (C) is free of cationic polymers.
Process according to any one of the preceding claims, in which composition (C) comprises a total content of cationic surfactants of less than 5% by weight, preferably less than 2% by weight, more preferentially less than 1% by weight, even more preferentially less than 0.1% by weight, most preferentially less than 0.01% by weight, and better still less than 0.001% by weight relative to the total weight of composition (C), and even better still composition (C) is free of cationic surfactants.
Process according to any one of the preceding claims, in which composition (C) comprises a total content of poly(oxyethylenated) compounds of less than 5% by weight, preferably less than 2% by weight, more preferentially less than 1% by weight, even more preferentially less than 0.1% by weight, most preferentially less than 0.01% by weight, and better still less than 0.001% by weight relative to the total weight of composition (C), and even better still composition (C) is free of poly(oxyethylenated) compounds.
Process according to any one of the preceding claims, in which composition (C) comprises a total water content of less than 30% by weight, preferably less than 10% by weight, more preferentially less than 5% by weight, even more preferentially less than 1% by weight, most preferentially less than 0.1% by weight, and better still less than 0.01% by weight relative to the total weight of composition (C), and even better still composition (C) is anhydrous.
Process according to any one of the preceding claims, in which composition (C) is liquid.
Process according to any one of the preceding claims, in which composition (C) comprises one or more organic solvents chosen from C₂-C₄ alcohols, polyols and polyol ethers, aromatic alcohols, hydrocarbon-based oils and mixtures thereof.
Process according to any one of the preceding claims, in which composition (C) is applied to dry or wet keratin fibres, preferably to wet keratin fibres.
Process according to the preceding claim, comprising at least one additional step following step i), chosen from steps ii) to iv) below:
ii) a step of applying composition (C) to the keratin fibres, preferably for a period of at least 10 seconds, said application step optionally being performed under an airtight film of wrapper or plastic film type;
iii) a step of rinsing and/or washing the keratin fibres;
iv) a step of drying the keratin fibres in ambient air or with the aid of a heating device.
Composition (C) as defined in any one of Claims 1 to 20.
Use of a composition (C) as defined in any one of Claims 1 to 20, for caring for keratin fibres, preferably for giving keratin fibres a soft and/or smooth feel and/or sheen, more preferentially for giving them a soft and/or smooth feel.
Use of a composition (C) as defined in any one of Claims 1 to 20, for protecting keratin fibres from moisture, preferably for limiting the formation of frizziness and/or the increase in volume of the head of hair in a humid environment.