A hair coloring process comprising exposing the hair to UV radiation and applying a composition comprising a (poly)carbodiimide compound, a specific polymer, and a coloring agent.

The hair coloring process using UV radiation and a (poly)carbodiimide compound with a polymer and coloring agent addresses the need for a durable, shampoo-resistant hair color that maintains hair integrity.

FR3163861A1Pending Publication Date: 2026-01-02LOREAL SA
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Patent Information

Application Number
FR2024006948
Authority / Receiving Office
FR · FR
Patent Type
Applications
Current Assignee / Owner
Filing Date
2024-06-27
Publication Date
2026-01-02

AI Technical Summary

Technical Problem

Existing hair coloring methods fail to provide a homogeneous, long-lasting color coating that is resistant to shampoos and external aggressions such as brushing and perspiration without damaging the hair.

Method used

A hair coloring process involving exposure to UV radiation followed by application of a composition containing a (poly)carbodiimide compound, a polymer with reactive carboxylic acid groups, and a coloring agent, which forms a durable and vibrant color that persists after shampooing.

Benefits of technology

The process results in a homogeneous and resilient colored coating on the hair that remains vibrant after shampooing, while preserving the hair's physical qualities and resisting external aggressors.

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Abstract

Title: Hair coloring process comprising exposing hair to UV radiation, and applying a composition comprising a (poly)carbodiimide compound, a particular polymer and a coloring agent. The present invention relates to a hair coloring process comprising: a) exposing hair to UV radiation; and b) applying to the hair at least one composition C comprising: - at least one (poly)carbodiimide compound; - at least one polymer comprising at least one reactive group selected from carboxylic acids; and - at least one coloring agent selected from pigments, direct dyes, and mixtures thereof.
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Description

Title of the invention: A hair coloring process comprising exposing the hair to UV radiation and applying a composition comprising a (poly)carbodiimide compound, a specific polymer, and a coloring agent

[0001] The present invention relates to a hair coloring process comprising exposing the hair to UV radiation, and applying a composition C comprising a (poly)carbodiimide compound, a polymer comprising at least one reactive group selected from carboxylic acids, and a coloring agent. technical field

[0002] In the field of hair keratin fiber coloring, it is already known to color hair keratin fibers by different techniques from direct dyes or pigments for non-permanent colorings or from dye precursors for permanent colorings.

[0003] There are essentially three types of hair coloring processes:

[0004] a) so-called permanent coloring which has the function of bringing about a significant change in the natural color and which uses oxidation dyes which penetrate the hair fiber and form the dye by a process of oxidative condensation;

[0005] b) non-permanent, semi-permanent or direct coloring, which does not implement the oxidative condensation process and resists 4 or 5 shampoos; consists of dyeing the keratin fibers with dyeing compositions containing direct dyes;

[0006] c) Temporary hair coloring that results in a change to the natural hair color that lasts from one shampoo to the next and serves to enhance or correct a previously achieved shade. It can also be considered a "makeup" process.

[0007] Another coloring method involves using pigments. Indeed, applying pigment to the surface of keratin fibers generally produces visible colors on dark hair, since the surface pigment masks the fiber's natural color. However, the colors obtained using this method have the disadvantage of being poorly resistant to shampoos and external agents such as sebum, perspiration, brushing, and / or friction.

[0008] There therefore remains a need for a hair coloring process which has the advantage of obtaining a homogeneous colored coating on the hair, while forming a coating that is resistant to shampoos and various aggressions that hair can undergo processes such as brushing and / or rubbing without degrading the cosmetic properties of the hair.

[0009] Thus, the aim of the present invention is to develop a hair coloring process which has the advantage of obtaining a homogeneous and smooth colored coating on the hair, while forming a coating that is resistant to shampoos and to the various aggressions that hair can undergo such as brushing and / or rubbing without damaging the hair. Description of the invention

[0010] The present invention therefore relates to a hair coloring process comprising:

[0011] a) exposure of the hair to UV radiation; and

[0012] b) the application to the hair of at least one composition C comprising:

[0013] - at least one (poly)carbodiimide compound;

[0014] - at least one polymer comprising at least one reactive group selected from the carboxylic acids; and

[0015] - at least one coloring agent selected from pigments, direct colorants, and their mixtures.

[0016] Thanks to the hair coloring process according to the invention, colored coatings are applied to the hair, resulting in a visible color that remains vibrant even after shampooing, while preserving the hair's physical qualities. Such a coating can be resistant to external aggressors such as blow-drying and perspiration. In particular, it allows for a homogeneous application.

[0017] By "residual shampoo colour" in the context of the present invention, the colour obtained persists after one shampoo, preferably after 5 shampoos.

[0018] The expression "at least one" means one or more.

[0019] Unless otherwise indicated, the bounds of a range of values ​​are included in that range, in particular in the expressions "between" and "ranging from ... to ...".

[0020] The invention is not limited to the illustrated examples. The features of the different examples can, in particular, be combined within non-illustrated variants.

[0021] For the purposes of the present invention and, unless otherwise indicated,

[0022] - an "alkyl" radical designates a saturated linear or branched radical containing by example of 1 to 20 carbon atoms;

[0023] - an "aminoalkyl" radical means an alkyl radical as defined above, said alkyl radical comprising an NH2 group;

[0024] - a "hydroxyalkyl" radical means an alkyl radical as defined above, said alkyl radical comprising an OH group;

[0025] - an "alkylene" radical designates a divalent saturated hydrocarbon group at C2-C4, linear or branched, such as methylene, ethylene, or propylene;

[0026] - a "cycloalkyl" or "alicycloalkyl" radical designates a hydrocarbon group saturated cyclic mono- or polycyclic, preferably monocyclic, comprising from 1 to 3 rings, preferably 2 rings, and comprising from 3 to 24 carbon atoms, in particular comprising from 3 to 20 carbon atoms, more particularly from 3 to 13 carbon atoms, even more particularly from 3 to 12 carbon atoms, preferably between 5 and 10 carbon atoms, such as cyclopropyl, cyclopentyl, cyclohexyl, cycloheptyl, or norbornyl, in particular cyclopropyl, cyclopentyl, or a cyclohexyl. It being understood that the cycloalkyl radical may be substituted by one or more (Ci-C4)alkyl groups such as methyl, preferably the cycloalkyl radical is then an isoboromyl group.

[0027] - a "cycloalkylene" radical designates a divalent cycloalkyl group with " cycloalkyl” as defined above, preferably in C3-Ci2;

[0028] - an "aryl" radical is an unsaturated and aromatic hydrocarbon cyclic radical, comprising from 6 to 14 carbon atoms, preferably between 6 and 12 carbon atoms, mono / bi / or tri / cyclic, fused or not, preferably the aryl group comprises 1 ring of 6 carbon atoms such as phenyl, naphthyl, anthryl, phenanthryl and biphenyl, it being understood that the aryl radical may be substituted by one or more (CrC4)alkyl groups such as methyl, preferably tolyl, xylyl, or methylnaphthyl, preferably the aryl group represents phenyl;

[0029] - an "arylene" radical is a divalent aryl radical with "aryl" as defined previously preferred arylene represents phenylene;

[0030] - a "heterocyclic" radical designates a mono or polycyclic, saturated or unsaturated, non-aromatic or aromatic, comprising one or more heteroatoms preferably of 1 to 5 atoms chosen from O, S or N, comprising from 3 to 20 links preferably between 5 and 10 links such as imidazolyl, pyrrolyl and furanyl;

[0031] - a "heterocycloalkylene" radical is a divalent heterocyclic group with "heterocyclic" as defined above;

[0032] - an "aryloxy" radical designates an aryl-oxy radical with "aryl" as defined previously;

[0033] - an "alkoxy" radical designates an alkyl-oxy radical with "alkyl" as defined previously;

[0034] - an "acyloxy" radical designates an ester radical RC(O)-O- with R an alkyl group as defined previously;

[0035] - a "reactive" group is a group capable of forming a bond covalent with another group, identical or different, by chemical reaction.

[0036] Unless otherwise indicated, when compounds are mentioned in this application, this also includes their optical isomers, their geometric isomers, their tautomers, their salts, alone or in mixtures.

[0037] By "capillary keratin fibers" is meant hair. In other words, the expressions "capillary keratin fibers" and "hair" are equivalent in the remainder of the description.

[0038] For the purposes of the present invention, "hair" means the hair on the head. This term does not include body hair, eyebrows, or eyelashes. Hair exposure to UV radiation

[0039] As stated above, the process according to the invention comprises a) exposing the hair to UV radiation.

[0040] Thus, UV radiation can be UVA radiation, UVB radiation or UVC radiation.

[0041] As is known, UVA radiation has a wavelength ranging from 315 to 400 nm. UVB radiation has a wavelength ranging from 280 to 315 nm. UVC radiation has a wavelength ranging from 100 to 280 nm.

[0042] Advantageously, the exposure of the hair to said UV radiation, during step a), lasts for a period of at least 5 seconds, preferably for a period ranging from 10 seconds to 3 hours, more preferably from 50 seconds to 3 hours.

[0043] Advantageously, UV radiation is generated by any equipment incorporating a UV lamp, for example a UV lamp or a hair clip equipped with a lamp capable of delivering UV radiation.

[0044] Advantageously, UV radiation has an energy exposure (amount of energy per unit area) ranging from 0.5 to 50 W / cm2, preferably between 0.5 and 8 W / cm2, more preferably between 0.5 and 5 W / cm2.

[0045] Advantageously, UV radiation is chosen from UVB radiation with a wavelength ranging from 280 to 315 nm and UVC radiation with a wavelength ranging from 100 to 280 nm, preferably UVC radiation with a wavelength ranging from 100 to 280 nm.

[0046] As previously stated, the method according to the invention also includes b) applying to the hair at least one composition C comprising:

[0047] - at least one (poly)carbodiimide compound;

[0048] - at least one polymer comprising at least one reactive group selected from the carboxylic acids; and

[0049] - at least one coloring agent selected from pigments, direct colorants, and their mixtures.

[0050] According to a first preferred embodiment, step a) is followed by step b). In this embodiment, the exposure of the hair to UV radiation is carried out as a pretreatment.

[0051] According to a second embodiment, step b) is followed by step a). In this embodiment, the exposure of the hair to UV radiation is carried out in post-treatment.

[0052] Preferably, step a) is followed by step b) or step b) is followed by step a). According to this preference, step a) and step b) are not applied simultaneously. Polycarbodiimide compound

[0053] Composition C used in the process according to the invention comprises at least one (poly)carbodiimide compound.

[0054] The composition may comprise at least two distinct (poly)carbodiimide compounds, present in mixture in the composition.

[0055] The term "(poly)carbodiimide compound" means a compound comprising one or more carbodiimide group(s), preferably at least two carbodiimide groups, more preferably at least three carbodiimide groups; in particular, the number of carbodiimide groups does not exceed 200, preferably 150, more preferably 100.

[0056] The term “carbodiimide group” means a divalent linear triatomic fraction of general formula - (N=C=N) -.

[0057] The (poly)carbodiimide compound(s) according to the invention may optionally comprise in their structure one or more reactive groups other than carbodiimide groups, selected from alkoxysilyl, hydroxysilyl, acetoxysilyl, vinylsilyl, acrylalkylsilyl, methacrylalkylsilyl, crotonylalkylsilyl, carboxyanhydridoalkylsilyl, carboxyalkylsilyl, hydroxyalkylsilyl, aldehydoalkylsilyl, mercaptoalkylsilyl, norbomenylsilyl, acylpentadienylalkylsilyl, maleimidoalkylsilyl, sulfonylmylalkylsilyl, (meth)acrylalkyl, crotonylalkyl, alkyl epoxide such as propyl epoxide or butyl epoxide and azacyclopropane.

[0058] The reactive group(s) other than the carbodiimide groups may be pendant or terminal. Preferably, the (poly)carbodiimide compound(s) comprise one or more terminal groups other than the carbodiimide groups, preferably one or more terminal groups selected among the groups alkoxysilyl, hydroxysilyl, acetoxysilyl, vinylsilyl, acrylalkylsilyl, methacrylalkylsilyl, crotonylalkylsilyl, carboxyanhydridoalkylsilyl, carboxyalkylsilyl, hydroxyalkylsilyl, aldehydoalkylsilyl, mercaptoalkylsilyl, norbornenylsilyl, acylpentadienylalkylsilyl, maleimidoalkylsilyl, sulfonylmylalkylsilyl, (meth)acrylalkyl, crotonylalkyl, alkyl epoxide such as propyl epoxide or butyl epoxide and azacyclopropane.

[0059] According to a particular embodiment, the (poly)carbodiimide compound is chosen from the compounds of the following formula (I):

[0060] in which:

[0061] - Xi and X2 represent, independently, an oxygen atom O, a sulfur atom S or an NH group;

[0062] - Ri and R2 independently represent a grouping chosen from a radical hydrocarbon, preferably alkyl, possibly interrupted by one or more heteroatoms, a group selected from the following groups: alkoxysilyl, hydroxysilyl, acetoxysilyl, vinylsilyl, acrylalkylsilyl, methacrylalkylsilyl, crotonylalkylsilyl, carboxyanhydridoalkylsilyl, carboxyalkylsilyl, hydroxyalkylsilyl, aldehydoalkylsilyl, mercaptoalkylsilyl, norbornenylsilyl, acylpentadienylalkylsilyl, maleimidoalkylsilyl, sulfonylmylsilyl, (meth)acrylalkyl, crotonylalkyl, alkyl epoxide such as propyl epoxide or butyl epoxide, and azacyclopropane, and a hydrocarbon radical, preferably alkyl, possibly interrupted by one or more heteroatoms and by one or more groups selected from the following groups: alkoxysilyl, hydroxysilyl, acetoxysilyl, vinylsilyl, acrylalkylsilyl, methacrylalkylsilyl, crotonylalkylsilyl, carboxyanhydridoalkylsilyl, carboxyalkylsilyl, hydroxyalkylsilyl, aldehyde alkylsilyl, mercaptoalkylsilyl, norbornenylsilyl,acylpentadienylalkylsilyl, maleimidoalkylsilyl, sulfonylmylalkylsilyl, (meth)acrylalkyl, crotonylalkyl, alkyl epoxides such as propyl epoxide or butyl epoxide, and azacyclopropane; ,

[0063] - n denotes an integer from 1 to 1000; and

[0064] - A is a monomer selected from the compounds below:

[0065] According to another embodiment, the (poly)carbodiimide compound is chosen from the compounds of the following formula (!'): (D 'NA 4— LJ m I ' 7 W A—N ÏJ

[0066] in which:

[0067] - Xi and X2 represent, independently, an oxygen atom O, a sulfur atom S or an NH group;

[0068] - Yiet Y2 represent, independently, a divalent organic radical chosen from a saturated aliphatic group in C36 at Ci or an aromatic or alkylaromatic group in C6 to C24, the aliphatic or aromatic group optionally comprising one or more non-pending heteroatoms, such as nitrogen atom, oxygen atom, sulfur atom, or combinations thereof;

[0069] - Zi and Z2 represent, independently, a reactive terminal group or a group inert terminal;

[0070] - as an inert terminal group, Zi and Z2 can represent, independently, a saturated aliphatic group, linear or branched or cyclic, in the C1 to C50 range, or an aromatic group in the C6 to C8 range, said aliphatic and aromatic groups comprising possibly from 1 to 10 heteroatoms chosen from nitrogen, oxygen, sulfur and their combinations, and the aliphatic or aromatic group may be partially or totally fluorinated; in this variant, Zi and Z2 comprise a CG linking group connecting Zi to Yi and Z2 to Y2, the CG group being a single covalent bond, a saturated CC bond, an unsaturated covalent CC bond, an amide group, an ester group, a carbonate group, a thioester group, an ether group, a urethane group, a thiourethane group or a urea group;

[0071] - as a reactive terminal group, Zi and Z2 can be chosen from the alkoxysilyl, hydroxysilyl, acetoxysilyl, vinylsilyl, acrylalkylsilyl, methacrylalkylsilyl, crotonylalkylsilyl, carboxyanhydridoalkylsilyl, carboxyalkylsilyl, hydroxyalkylsilyl, aldehydoalkylsilyl, mercaptoalkylsilyl, norbomenylsilyl, acylpentadienylalkylsilyl, maleimidoalkylsilyl, sulfonylalkylsilyl, (meth)acrylalkyl, crotonylalkyl, alkyl epoxide groups such as propyl epoxide or butyl epoxide and azacyclopropane;

[0072] - Q represents an organopolymer or an organo-oligomer comprising units repetitive saturated aliphatic groups, linear or branched or cyclic, or aromatic groups or alkylaromatic groups, coupled by repetitive carbonate, ester, ether, amide, urethane or urea bonds or their combinations;

[0073] - A represents a divalent aliphatic, aromatic, alkylaromatic or linear, saturated, branched or cyclic having from 2 to 30 carbon atoms, optionally including one or more non-pending heteroatoms, such as nitrogen atom, oxygen atom, sulfur atom, or combinations thereof, in the aliphatic chain or aromatic chain;

[0074] - r denotes an integer equal to 0 or 1;

[0075] - m denotes an integer from 0 to 1000, preferably equal to 0 or 1;

[0076] - m' designates an integer ranging from 0 to 1000, preferably equal to 0 or 1;

[0077] - n denotes an integer from 0 to 1000, preferably equal to 0 or 1, with m+ (m'*n ) > 2.

[0078] Preferably, Zi and Z2 represent, independently, a reactive terminal group, more preferably, Zi and Z2 represent, independently, a group selected from the following groups: alkoxysilyl, hydroxysilyl, acetoxysilyl, vinylsilyl, acrylalkylsilyl, methacrylalkylsilyl, crotonylalkylsilyl, carboxyanhydridoalkylsilyl, carboxyalkylsilyl, hydroxyalkylsilyl, aldehydoalkylsilyl, mercaptoalkylsilyl, norbomenylsilyl, acylpentadienylalk ylsilyl, maleimidoalkylsilyl, sulfonylalkylsilyl, (meth)acrylalkyl, crotonylalkyl, alkyl epoxide such as propyl epoxide or butyl epoxide, and azacyclopropane.

[0079] Such (poly)carbodümide compounds are marketed for example by the company Stahl BV, under the name Permutex XR, or under the name RelcaLinklO., under the name Picassian XL and Nisshinbo compounds marketed under the name CARBODILITE with the series V-02, V-02-L2, SV-02, E-02, V-10, SW-12G, E-03A, E-04DG-T, E-05, V-04, V-02B, V-04PF, V-05.

[0080] Preferably, the (poly)carbodiimide compound(s) is / are chosen from the compounds of the following formula (II): G (II),

[0081] in which:

[0082] - Xi and X2 represent, independently, an oxygen atom O, a sulfur atom S or an NH group;

[0083] - Ri and R2 independently represent a hydrocarbon radical possibly interrupted by one or more heteroatom(s);

[0084] - n and z denote an integer from 1 to 20, with n+z > 2 and w denotes a integer ranging from 1 to 3;

[0085] - Li independently represents a divalent aliphatic hydrocarbon radical in Cr Cig, a C3-Ci5 cycloalkylene radical, a C3-Ci2 heterocycloalkylene group, or a C6-Ci4 arylene group, and mixtures thereof;

[0086] - E independently represents a grouping chosen from:

[0087] - -O-R3-O-; -S-R4-S-; -R5-N(R6)-R4-N(R6)-R5-,

[0088] in which R3 and R4 independently represent a divalent hydrocarbon radical possibly interrupted by one or more heteroatom(s);

[0089] - R5 independently represents a covalent bond or a hydrocarbon radical saturated divalent, possibly interrupted by one or more heteroatom(s);

[0090] - R6 independently represents a hydrogen atom, or a hydrocarbon radical possibly interrupted by one or more heteroatom(s).

[0091] The term “hydrocarbon radical” means a saturated or unsaturated, linear or branched radical having from 1 to 300 carbon atoms, preferably from 1 to 250 carbon atoms, more preferably from 1 to 200 carbon atoms. Preferably, the hydrocarbon radical is a linear and saturated radical.

[0092] The hydrocarbon radical may comprise one or more cyclic groups.

[0093] The hydrocarbon radical can be interrupted by one or more heteroatom(s), in particular chosen from O, S or N and / or substituted by one or more cation(s), anion(s), or zwitterion(s) or cationic group(s) such as ammonium, anionic group(s) such as carboxylate, or zwitterionic group(s), and / or comprising a metal ion which can be incorporated in the form of a salt.

[0094] The term "heteroatom(s)" means an oxygen atom O, a sulfur atom S or a nitrogen atom N, as well as halogen atoms such as Cl, F, Br and I. If the heteroatom is included in the chain of the hydrocarbon radical, the heteroatom is preferably chosen from among the oxygen atoms O, sulfur atoms S or nitrogen atoms N.

[0095] Preferably, Xi and X2 independently represent an oxygen atom.

[0096] Preferably, Ri and R2 are chosen independently from dialkylaminoalcohols, alkyl esters of hydroxycarboxylic acid and monoalkyl ethers of (poly)alkylene glycol, in which a hydroxy group has been removed, and mixtures thereof.

[0097] According to a preferred embodiment, Ri and R2 are chosen independently from the following groupings (i) to (iv):

[0098] (i) the compound of the following formula (III):

[0099] R7-OC(O)-C(R8)(H)-(III),

[0100] wherein R7 represents a Ci-C3 alkyl group, and R8 represents a hydrogen atom or a Ci-C3 alkyl group, preferably R7 is a methyl and R8 is a hydrogen atom or a methyl.

[0101] (ii) the compound of the following formula (IV):

[0102] R9-[0-CH2-C(H)(Rio)]p-(IV),

[0103] wherein R9 represents a Ci-C4 alkyl group, Rio represents a hydrogen atom or a Ci-C4 alkyl group and p denotes an integer from 1 to 3; preferably, R9 is a methyl, ethyl or butyl and R10 is a hydrogen atom or a methyl and p is equal to 1.

[0104] (iii) the compound of the following formula (V):

[0105] (Rh)2N-CH2-C(H)(Ri2)- (V),

[0106] wherein Ru represents a Ci-C4 alkyl group and R[2 represents a hydrogen atom or a CrC4 alkyl group; preferably Ru is a methyl, ethyl or butyl and R[2 is a hydrogen atom or a methyl.

[0107] (iv) the compound of the following formula (VI):

[0108] R13-[O-CH2-C(H)(R14)]q- (VI),

[0109] wherein Rn represents a Ci-C4 alkyl group or a phenyl, R[4 represents a hydrogen atom or a CrC4 alkyl group and q denotes an integer from 4 to 30; preferably Rn is a methyl, ethyl or butyl and R[4 is a hydrogen atom or a methyl.

[0110] Preferably, Ri and R2 independently represent a compound of formula (VI) in which Rn represents a CrC4 alkyl group or a phenyl, preferably a Ci-C4 alkyl group, more preferably a methyl, R[4] represents a hydrogen atom or a CrC4 alkyl group, preferably a hydrogen atom and q denotes an integer from 4 to 30.

[0111] According to an alternative embodiment, Ri and R2 are different and one of the radicals Ri or R2 represents a compound of formula (IV) as described above and the other radical Ri or R2 represents a compound of formula (VI) as described above.

[0112] Preferably, in formula (IV), R9 is a methyl, ethyl or butyl and Rio is a hydrogen atom or a methyl and p is equal to 1.

[0113] Preferably, in formula (VI), Rn is a methyl, ethyl or butyl and RM is a hydrogen atom or a methyl and q denotes an integer from 4 to 30.

[0114] According to another alternative embodiment, Ri and R2 are identical and represent a compound of formula (VI) in which Rn represents a CrC4 alkyl group or a phenyl, preferably a CrC4 alkyl group, more preferably a methyl, R[4] represents a hydrogen atom or a Ci-C4 alkyl group, preferably a hydrogen atom and q denotes an integer from 4 to 30.

[0115] Preferably, n denotes an integer from 1 to 20, more preferably from 2 to 20.

[0116] Preferably, z denotes an integer from 1 to 20, more preferably from 2 to 20.

[0117] Preferably, w is equal to 1.

[0118] Preferably, w is equal to 1, n+z denotes an integer from 4 to 10.

[0119] Preferably, Li is chosen from a divalent aliphatic hydrocarbon radical in Ci -Ci8 such as methylene, ethylene, and propylene, a C3-C15 cycloalkylene radical such as cyclopentylene, cycloheptylene, and cyclohexylene, a C3-Ci2 heterocycloalkylene group such as imidazolene, pyrrolene, and furanylene, or a C6-Ci4 arylene group such as phenylene, and mixtures thereof.

[0120] For example, Li can be selected from a radical derived from tolylene diisocyanate, hexamethylene diisocyanate, xylylene diisocyanate, 2,2,4-trimethylhexamethyl diisocyanate, 1,12-diisocyanate dodecane, norbornane diisocyanate,

[0121] 2,4-bis-(8-isocyanateoctyl)-1,3-dioctylcyclobutane, 4,4'-dicylclohexyhnethane diisocyanate, tetramethylxylylene diisocyanate, isophorone diisocyanate, 1,5-naphthylene diisocyanate, 4,4'-diphenylmethane diisocyanate, 4,4'-diphenyldimethylmethane diisocyanate and phenylene diisocyanate and mixtures thereof. Preferably, Li is chosen from a C3-Ci5 cycloalkylene radical, or a C6-Ci4 arylene group and mixtures thereof, such as the compounds of the following formula (VII):

[0122] Preferably, L1 is the 4,4-dicyclohexylene methane corresponding to the following formula (VIII): (VIII).

[0123] According to another embodiment, when L1 is an arylene group in C6-Ci4, Li is not the m-tetramethylxylylene radical represented by the following formula (IX): (IX).

[0124] As stated previously, E independently represents a grouping chosen from:

[0125] - -O-R3-O-; -S-R4-S-; -R5-N(R6)-R4-N(R6)-R5-;

[0126] in which R3 and R4 independently represent a divalent hydrocarbon radical possibly interrupted by one or more heteroatom(s);

[0127] - R5 independently represents a covalent bond or a hydrocarbon radical saturated divalent, possibly interrupted by one or more heteroatom(s); and

[0128] - R6 independently represents a hydrogen atom, or a hydrocarbon radical possibly interrupted by one or more heteroatom(s).

[0129] Preferably, R3 and R4 are chosen independently from a C6-C14 arylene radical such as phenylene, a C3-Ci2 cycloalkylene radical such as cyclopropylene and cyclobutylene, a linear or CrCi8 branched alkylene radical such as methylene and ethylene, optionally interrupted by one or more heteroatom(s) and mixtures thereof.

[0130] More preferably, R3 and R4 are chosen independently from a linear or CrCi8 branched alkylene radical such as methylene, butylene, propylene, ethylene, optionally interrupted by one or more heteroatom(s).

[0131] Preferably, when R5 is not a covalent bond, R5 is selected from a C6-Ci4 arylene radical such as phenylene, a C3-Ci2 cycloalkylene radical such as cyclopropylene and cyclobutylene, a linear or branched Ci-Ci8 alkylene radical such as methylene and ethylene, optionally interrupted by one or more heteroatom(s), and mixtures thereof.

[0132] Preferably, R6 is selected from a C6-Ci4 arylene radical such as phenylene, a C3-Ci2 cycloalkylene radical such as cyclopropylene and cyclobutylene, a linear or branched CrCi8 alkylene radical such as methylene and ethylene, optionally interrupted by one or more heteroatom(s), and mixtures thereof.

[0133] Preferably, E represents an -O-R3-O- group in which R3 is selected from a C6-Ci4 arylene radical, a C3-Ci2 cycloalkylene radical, a linear or branched CrCi8 alkylene radical, optionally interrupted by one or more heteroatom(s), and mixtures thereof.

[0134] More preferably, E represents a -O-R3-O- group in which R3 represents a linear or CrCi8 branched alkylene radical such as methylene, butylene, propylene, ethylene, optionally interrupted by one or more heteroatom(s).

[0135] According to a particular embodiment, the (poly)carbodiimide compound is a copolymer derived from alpha-methylstyryl-isocyanates of the following formula (X): (X),

[0136] in which R independently represents an alkyl group having from 1 to 24 carbon atoms, a cycloalkyl group having from 3 to 24 carbon atoms or an aryl group having from 6 to 24 carbon atoms, and,

[0137] n denotes an integer from 2 to 100.

[0138] In this embodiment, the term “alkyl group” is as defined above.

[0139] In this embodiment, the term "cycloalkyl group" is as defined above.

[0140] In this embodiment, n can denote an integer from 2 to 50, preferably from 3 to 30, more preferably from 5 to 10.

[0141] According to another particular embodiment, the (poly)carbodiimide compound is a compound of the following formula (XI):

[0142] in which R independently represents an alkyl group having from 1 to 24 carbon atoms, a cycloalkyl group having from 3 to 24 carbon atoms, or an aryl group having from 6 to 24 carbon atoms.

[0143] The "alkyl group", the "cycloalkyl group" and the "aryl group" are as defined above.

[0144] According to a preferred embodiment, the (poly)carbodiimide compound is selected from compounds of formula (I) or formula (II) in which:

[0145] - Xi and X2 independently represent an oxygen atom;

[0146] - Ri and R2 are chosen independently from among the dialkylaminoalcohols, the alkyl esters of hydroxycarboxylic acid and monoalkyl ethers of (poly)alkylene glycol, in which a hydroxy group has been removed, and mixtures thereof, preferably monoalkyl ethers of (poly)alkylene glycol, in which a hydroxy group has been removed, more preferably the compound of formula (VI) as described above, in which Rn represents a group alkyl in C1-C4 or a phenyl, preferably an alkyl group in C1-C4, more preferably a methyl, R[4 represents a hydrogen atom or an alkyl group in CrC4, preferably a hydrogen atom and q denotes an integer from 4 to 30;

[0147] - n and z, when present, denote an integer from 1 to 20, with n +z > 2 and w is equal to 1;

[0148] - Li, when present, is chosen from an aliphatic hydrocarbon radical divalent in CrCi8, a cycloalkylene radical in C3-Ci5, a heterocycloalkylene group in C3-Ci2, or an arylene group in C6-Ci4, and mixtures thereof, preferably a cycloalkylene radical in C3-Ci5;

[0149] - A, when present, is chosen from an aliphatic hydrocarbon radical divalent in CrCi8, a cycloalkylene radical in C3-Ci5, a heterocycloalkylene group in C3-Ci2, or an arylene group in C6-Ci4, and mixtures thereof, preferably a cycloalkylene radical in C3-Ci5;

[0150] - E, when present, independently represents a grouping chosen from:

[0151] - -O-R3-O-; -S-R4-S-; -R5-N(R6)-R4-N(R6)-R5-;

[0152] wherein R3 and R4 are independently selected from a C6-Ci4 arylene radical, a C3-Ci2 cycloalkylene radical, a linear or branched CrCi8 alkylene radical, optionally interrupted by one or more heteroatom(s), and mixtures thereof;

[0153] - when R5 is not a covalent bond, R5, when present, is chosen including a C6-Ci4 arylene radical, a C3-Ci2 cycloalkylene radical, a linear or branched CrCi8 alkylene radical, possibly interrupted by one or more heteroatoms, and mixtures thereof; and

[0154] - R6, when present, is chosen from a C6-Ci4 arylene radical, a cycloalkylene radical in C3-Ci2, a linear or branched alkylene radical in CrCi8, possibly interrupted by one or more heteroatom(s), and mixtures thereof.

[0155] Preferably, the (poly)carbodiimide compound is chosen from compounds of formula (II) in which:

[0156] - Xi and X2 independently represent an oxygen atom;

[0157] - Ri and R2 are chosen independently from among the dialkylaminoalcohols, the alkyl esters of hydroxycarboxylic acid and monoalkyl ethers of (poly)alkylene glycol, in which a hydroxy group has been removed, and mixtures thereof;

[0158] - n and z denote an integer from 1 to 20, with n+z > 2 and w is equal to 1;

[0159] - Li is chosen from a divalent aliphatic hydrocarbon radical in CrCi8, a cycloalkylene radical at C3-Ci5, a heterocycloalkylene group at C3-Ci2, or an arylene group at C6-Ci4, and mixtures thereof;

[0160] - E independently represents a grouping chosen from:

[0161] - -O-R3-O-; -S-R4-S-; -R5-N(R6)-R4-N(R6)-R5-;

[0162] wherein R3 and R4 are independently selected from a C6-Ci4 arylene radical, a C3-Ci2 cycloalkylene radical, a linear or branched CrCi8 alkylene radical, optionally interrupted by one or more heteroatom(s), and mixtures thereof;

[0163] - when R5 is not a covalent bond, R5 is chosen from an arylene radical in C6-Ci4, a C3-Ci2 cycloalkylene radical, a linear or branched Ci-Ci8 alkylene radical, possibly interrupted by one or more heteroatoms, and mixtures thereof; and

[0164] - R6 is chosen from a C6-Ci4 arylene radical, a C3-Ci2 cycloalkylene radical, a linear or branched CrCi8 alkylene radical, possibly interrupted by one or more heteroatom(s), and mixtures thereof.

[0165] More preferably, the (poly)carbodiimide compound is chosen from compounds of formula (II) in which:

[0166] - Xi and X2 independently represent an oxygen atom;

[0167] - Ri and R2, are independently of (poly)alkylene glycol monoalkyl ethers, in which a hydroxy group has been removed;

[0168] - n and z denote an integer from 1 to 20, with n+z > 2 and w is equal to 1;

[0169] - Li is a C3-Ci5 cycloalkylene radical;

[0170] - E independently represents a grouping chosen from:

[0171] - -O-R3-O-; -S-R4-S-; -R5-N(R6)-R4-N(R6)-R5-;

[0172] wherein R3 and R4 are independently selected from a C6-Ci4 arylene radical, a C3-Ci2 cycloalkylene radical, a linear or branched Ci-Ci8 alkylene radical, optionally interrupted by one or more heteroatom(s), and mixtures thereof;

[0173] - when R5 is not a covalent bond, R5 is chosen from an arylene radical in C6-Ci4, a C3-Ci2 cycloalkylene radical, a linear or branched Ci-Ci8 alkylene radical, possibly interrupted by one or more heteroatoms, and mixtures thereof; and

[0174] - R6 is chosen from a C6-Ci4 arylene radical, a C3-Ci2 cycloalkylene radical, a linear or branched Ci-Ci8 alkylene radical, possibly interrupted by one or more heteroatom(s), and mixtures thereof.

[0175] Even more preferably, the (poly)carbodiimide compound is chosen from compounds of formula (II) in which:

[0176] - Xi and X2 independently represent an oxygen atom;

[0177] - Ri and R2, independently represent the compound of the following formula (VI):

[0178] R13-[O-CH2-C(H)(R14)]q- (VI),

[0179] wherein Rn represents a C1-C4 alkyl group or a phenyl, preferably a C1-C4 alkyl group, more preferably a methyl, R[4] represents a hydrogen atom or a CrC4 alkyl group, preferably a hydrogen atom and q denotes an integer from 4 to 30;

[0180] - n and z denote an integer from 1 to 20, with n+z ranging from 4 to 10 and w is equal to 1;

[0181] - Li is a C3-C15 cycloalkylene radical such as cyclopentylene, the cycloheptylene, cyclohexylene, and 4,4-dicyclohexylene methane; and

[0182] - E represents a grouping -O-R3-O- in which R3 is chosen from a radical arylene in C6-Ci4, a cycloalkylene radical in C3-Ci2, a linear or branched alkylene radical in Ci-Ci8, possibly interrupted by one or more heteroatom(s), and mixtures thereof.

[0183] Even more preferably, the (poly)carbodiimide compound is chosen from compounds of formula (II) in which:

[0184] - Xi and X2 independently represent an oxygen atom;

[0185] - Ri and R2, independently represent the compound of the following formula (VI):

[0186] R13-[O-CH2-C(H)(R14)]q- (VI)

[0187] wherein R13 represents a CrC4 alkyl group or a phenyl, preferably a CrC4 alkyl group, more preferably a methyl, R[4 represents a hydrogen atom or a CrC4 alkyl group, preferably a hydrogen atom and q denotes an integer from 4 to 30;

[0188] - n and z denote an integer from 1 to 20, with n+z ranging from 4 to 10 and w is equal to 1;

[0189] - Li is a C3-Ci5 cycloalkylene radical such as cyclopentylene, the cycloheptylene, cyclohexylene, 4,4-dicyclohexylene methane, preferably 4,4-dicyclohexylene methane; and

[0190] - E represents a group- -O-R3-O- in which R3 represents a radical linear or CrCi8 branched alkylene such as methylene, propylene, butylene ethylene, possibly interrupted by one or more heteroatom(s).

[0191] According to a preferred embodiment, the (poly)carbodiimide compound is a compound of the following formula (XII):

[0192] in which L1 is 4,4-dicyclohexylene methane, n and z denote an integer from 1 to 20, with n+z ranging from 4 to 10, E represents an -O-R3-O- group in which R3 represents a linear or Ci-Ci8 branched alkylene radical such as methylene, propylene, butylene ethylene, optionally interrupted by one or more heteroatom(s), and r and s denote an integer from 4 to 30.

[0193] Advantageously, the (poly)carbodiimide compound(s) as defined above are present in a total content ranging from 0.01 to 20% by weight, preferably from 0.1 to 15% by weight, more preferably from 0.2 to 10% by weight, even more preferably from 0.5 to 8% by weight, better from 1 to 6% by weight relative to the total weight of composition C.

[0194] Polymer comprising at least one reactive group selected from carboxylic acids

[0195] Composition C used in the process according to the invention comprises at least one polymer comprising at least one reactive group selected from carboxylic acids, preferably at least one acrylic polymer.

[0196] Preferably, the acrylic polymer(s) are in the form of aqueous dispersions of acrylic polymer particles, more preferably in the form of aqueous dispersions of film-forming acrylic polymer particles.

[0197] Thus, preferably, composition C comprises at least one acrylic polymer in the form of aqueous dispersions of acrylic polymer particles.

[0198] The dispersion(s) may be simple dispersions in the aqueous medium of the cosmetic composition. Latexes are a particular example of a dispersion.

[0199] For the purposes of this invention, "polymer" means a compound consisting of the repetition of one or more motifs (these motifs being derived from compounds called monomers). This motif or these motifs are repeated at least twice and preferably at least three times.

[0200] By "film-forming polymer" is meant a polymer capable of forming, alone or in the presence of an auxiliary film-forming agent, a macroscopically continuous film on a substrate, in particular on hair, and preferably a cohesive film

[0201] For the purposes of this invention, "acrylic polymer" means a polymer synthesized from at least one monomer selected from (meth)acrylic acid and / or (meth)acrylic acid ester and / or (meth)acrylic acid amide.

[0202] The motif(s) derived from the (meth)acrylic acid monomers of the polymer may (may) optionally be in the form of salt(s), in particular of alkali metal, alkaline earth metal, ammonium or organic base.

[0203] Esters of (meth)acrylic acid (also called (meth)acrylates) are advantageously chosen from among alkyl (meth)acrylates, in particular alkyl acrylates in C1 to C30, preferably in C1 to C20, better in C1 to Cm, aryl (meth)acrylates, in particular aryl acrylates in C6 to C10, hydroxyalkyl (meth)acrylates, in particular hydroxyalkyl acrylates in C2 to C6.

[0204] Among the alkyl (meth)acrylates, we can mention methyl (meth)acrylate, ethyl (meth)acrylate, butyl (meth)acrylate, isobutyl (meth)acrylate, ethyl-2 hexyl (meth)acrylate, lauryl (meth)acrylate, cyclohexyl (meth)acrylate.

[0205] Among the hydroxyalkyl (meth)acrylates, we can mention hydroxyethyl acrylate, 2-hydroxypropyl acrylate, hydroxyethyl methacrylate, 2-hydroxypropyl methacrylate.

[0206] Among the aryl (meth)acrylates, benzyl acrylate and phenyl acrylate can be cited.

[0207] Particularly preferred esters of (meth)acrylic acid are the Alkyl (meth)acrylates, preferably alkyl in C1 to C30, more preferably in C1 to C20, even better in C1 to C10, and even more particularly in C1 to C4.

[0208] According to the present invention, the alkyl group of the esters can be fluorinated, or even perfluorinated, that is to say that part or all of the hydrogen atoms of the alkyl group are substituted by fluorine atoms.

[0209] Examples of (meth)acrylic acid amides include (meth)acrylamides, as well as N-alkyl (meth)acrylamides, particularly alkyl in C2 to C12. Among the N-alkyl (meth)acrylamides, examples include N-ethyl acrylamide, Nt-butyl acrylamide, Nt-octyl acrylamide and N-undecylacrylamide.

[0210] The acrylic polymer according to the invention can be a homopolymer or a copolymer, advantageously a copolymer, even better a copolymer of (meth)acrylic acid and (meth)acrylic acid esters.

[0211] Preferably, the acrylic polymer(s) according to the invention comprise one or more motifs derived from the following monomers:

[0212] a) (meth)acrylic acid; and

[0213] b) alkyl (meth)acrylate in C30 Ci, more preferably in C20 Ci, even better in Cm Ci, and even more particularly in C4 Ci.

[0214] Preferably, the aqueous dispersion of acrylic polymer particles does not comprise a surfactant. The term "surfactant" means any agent capable of modifying the surface tension between two surfaces.

[0215] Among the acrylic polymers according to the invention, we can mention the copolymers of (meth)acrylic acid and methyl or ethyl (meth)acrylate, in particular the copolymers of methacrylic acid and ethyl acrylate such as the compound sold under the trade name LUVIMER MAE by BASF, or the Polyacrylate-2 crosspolymer compound sold under the trade name FIXATE SUPERHOLD POLYMER by LUBRIZOL, or the Acrylate Copolymer compound sold under the trade name DAITOSOL 3000VP3 by DAITO KASEI KOGYO, or the Acrylate Copolymer compound sold under the trade name DAITOSOL 3000SLPN-PE1 by DAITO KASEI KOGYO.

[0216] The acrylic polymer may optionally comprise one or more additional monomers, other than the (meth)acrylic acid and / or (meth)acrylic acid ester and / or (meth)acrylic acid amide monomers.

[0217] As an additional monomer, examples include styrenic monomers, in particular styrene and alpha-methylstyrene, and preferably styrene.

[0218] In particular, the acrylic polymer may be a styrene / (meth)acrylate copolymer, and in particular a polymer selected from copolymers resulting from the polymerization of at least one styrenic monomer and at least one alkyl (meth)acrylate monomer in C1 to C20, preferably in C1 to C10.

[0219] The alkyl (meth)acrylate monomer in C1 to C10 can be selected from methyl acrylate, ethyl acrylate, propyl acrylate, butyl acrylate, hexyl acrylate, octyl acrylate, 2-ethyl hexyl acrylate.

[0220] As an acrylic polymer, we can cite the styrene / (meth)acrylate(s) copolymers marketed under the name JONCRYL 77 by BASF, under the name YODOSOL GH41F by AKZO NOBEL and under the name SYNTRAN 5760 CG by INTERPOLYMER.

[0221] Preferably, composition C comprises at least one aqueous dispersion of acrylic polymer particles. More preferably, composition C comprises at least one aqueous dispersion of acrylic polymer particles comprising one or more motifs derived from the following monomers:

[0222] a) (meth)acrylic acid; and

[0223] b) alkyl (meth)acrylate in C1 to C30, preferably in C1 to C20, more preferably in C1 to C10, and even more particularly in C1 to C4.

[0224] Preferably, the aqueous dispersion of acrylic polymer particles has an acrylic polymer(s) (or active material, or dry matter) content on the basis of the weight of the dispersion of 20 to 60% by weight, more preferably of 22 to 55% by weight and even better of 25 to 50% by weight.

[0225] Advantageously, the total content of the polymer(s) comprising at least one reactive group selected from carboxylic acids ranges from 0.1 to 35% by weight, more preferably from 0.5 to 30% by weight, better still from 1 to 20% by weight, and even more preferably from 3 to 15% by weight relative to the total weight of composition C.

[0226] Advantageously, the total content of the acrylic polymer(s) ranges from 0.1 to 35% by weight, more preferably from 0.5 to 30% by weight, better still from 1 to 20% by weight, and even more preferably from 3 to 15% by weight relative to the total weight of composition C.

[0227] According to a particular embodiment, the total content of the aqueous dispersion(s) of acrylic polymer particle(s) preferably ranges from 0.1 to 35% by weight, more preferably from 0.5 to 30% by weight, even better from 1 to 20% by weight, and even more preferably from 3 to 15% by weight relative to the total weight of composition C. Coloring agent

[0228] Composition C used in the process according to the invention comprises at least one colouring agent selected from pigments, direct colorants, and mixtures thereof.

[0229] Preferably, composition C used in the process according to the invention comprises at least one pigment.

[0230] The term "pigment" means all pigments that impart color to keratinous materials. Their solubility in water at 25 °C and atmospheric pressure (760 mmHg) is less than 0.05% by weight, and preferably less than 0.01%.

[0231] The pigments that can be used are in particular chosen from among the organic and / or mineral pigments known in the art, in particular those described in Kirk-Othmer's Encyclopedia of Chemical Technology and in Ullmann's Encyclopedia of Industrial Chemistry.

[0232] They may be natural, of natural origin, or not.

[0233] These pigments may be in the form of powder or pigment paste. They may be coated or uncoated.

[0234] Pigments can, for example, be chosen from mineral pigments, organic pigments, lacquers, special effect pigments such as mother-of-pearl or glitter, and mixtures thereof.

[0235] The pigment may be a mineral pigment. By mineral pigment, we mean any pigment that meets the definition in the Ullmann Encyclopedia in the chapter on inorganic pigments. Examples of mineral pigments useful in the present invention include iron or chromium oxides, manganese violet, ultramarine blue, chromium hydrate, ferric blue, and titanium dioxide.

[0236] The pigment may be an organic pigment. By "organic pigment" is meant any pigment that meets the definition in the Ullmann encyclopedia in the chapter on organic pigment.

[0237] The organic pigment may in particular be selected from the following compounds: nitroso, nitro, azo, xanthene, pyrene, quinoline, quinoline, anthraquinone, triphenylmethane, fluorane, phthalocyanine, metal complex type, isoindolinone, isoindoline, quinacridone, perinone, perylene, diketopyrrolopyrrole, indigo, thioindigo, dioxazine, triphenylmethane, quinophthalone.

[0238] In particular, white or colored organic pigments may be selected from carmine, carbon black, aniline black, azo yellow, quinacridone, phthalocyanine blue, the blue pigments coded in the Color Index under references Cl 42090, 69800, 69825, 74100, 74160, the yellow pigments coded in the Color Index under references Cl 11680, 11710, 19140, 20040, 21100, 21108, 47000, 47005, the green pigments coded in the Color Index under references Cl 61565, 61570, 74260, the orange pigments coded in the Color Index under reference CI 11725, 45370, 71105, the red pigments coded 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, phenolic derivatives as described in patent FR 2 679 771.

[0239] By way of example, one can also cite organic pigment pastes such as the products sold by the company HOECHST under the name:

[0240] - COSMENYL YELLOW IOG: Pigment YELLOW 3 (Cl 11710);

[0241] - COSMENYL YELLOW G: Pigment YELLOW 1 (Cl 11680);

[0242] - ORANGE COSMENYL GR: Pigment ORANGE 43 (Cl 71105);

[0243] - COSMENYL RED R: Pigment RED 4 (Cl 12085);

[0244] - CARMIN COSMENYL FB: Pigment RED 5 (Cl 12490);

[0245] - VIOLET COSMENYL RL: Pigment VIOLET 23 (Cl 51319);

[0246] - COSMENYL BLUE A2R: Pigment BLUE 15.1 (Cl 74160);

[0247] - COSMENYL GREEN GG: Pigment GREEN 7 (Cl 74260);

[0248] - COSMENYL BLACK R: Pigment BLACK 7 (Cl 77266).

[0249] The pigments according to the invention can also be in the form of composite pigments as described in patent EP 1 184 426. These composite pigments can be composed in particular of particles comprising an inorganic core, at least one binder ensuring the fixation of organic pigments on the core, and at least one organic pigment covering at least partially the core.

[0250] The organic pigment can also be a lake. By lake, we mean colorants adsorbed onto insoluble particles, the whole thus obtained remaining insoluble during use.

[0251] The inorganic substrates on which the dyes are adsorbed are, for example, alumina, silica, calcium sodium borosilicate or calcium aluminium borosilicate, and aluminium.

[0252] Among the colorants, we can mention carminic acid. We can also mention the colorants 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 1 O (CI 77 002), D & C Green 3 (CI 42 053), D & C Blue 1 (CI 42 090).

[0253] As examples of lacquers, we can cite the product known under the following name: D & C Red 7 (CI 15 850 :1).

[0254] The pigment can also be a special effects pigment. Special effects pigments are defined as pigments that generally create a non-uniform and changing colored appearance (characterized by a certain shade, vibrancy, and clarity) depending on the viewing conditions (light, temperature, viewing angles, etc.). They are thus distinct from colored pigments that provide a uniform opaque, semi-transparent, or conventionally transparent tint.

[0255] There are several types of special effect pigments, those with a low refractive index such as fluorescent or photochromic pigments, and those with a higher refractive index such as mother-of-pearl, interference pigments or glitter.

[0256] Examples of special effect pigments include pearlescent pigments such as titanium-coated mica or bismuth oxychloride, colored pearlescent pigments such as titanium-coated mica with iron oxides, iron oxide-coated mica, titanium-coated mica, particularly with ferric blue or chromium oxide, titanium-coated mica with an organic pigment as defined above, and bismuth oxychloride-based pearlescent pigments. Examples of pearlescent pigments include Cellini pearlescent pigments marketed by BASF (Mica-TiO2-lacquer), Prestige pearlescent pigments marketed by Eckart (Mica-TiO2), Prestige Bronze pearlescent pigments marketed by Eckart (Mica-Fe2O3), and Colorona pearlescent pigments marketed by Merck (Mica-TiO2-Fe2O3).

[0257] We can also mention gold-colored mother-of-pearl, notably marketed by BASF under the names Brilliant Gold 212G (Timica), Gold 222C (Cloisonne), Sparkle Gold (Timica), Gold 4504 (Chromalite) and Monarch Gold 233X (Cloisonne); bronze mother-of-pearl, notably marketed by MERCK under the names Bronze Fine (17384) (Colorona) and Bronze (17353) (Colorona) and by BASF under the name Super Bronze (Cloisonne); orange mother-of-pearl, notably marketed by BASF under the names Orange 363C (Cloisonne) and Orange MCR 101 (Cosmica) and by MERCK under the names Passion Orange (Colorona) and Matte Orange (17449) (Microna); brown-tinted mother-of-pearl, notably marketed by BASF under the names Nu-antique Copper 340XB (Cloisonne) and Brown CL4509 (Chromalite); copper-tinted mother-of-pearl, notably marketed by BASF under the name Copper 340A (Timica);red-tinted mother-of-pearl, notably marketed by MERCK under the name Sienna Fine (17386) (Colorona); yellow-tinted mother-of-pearl, notably marketed by BASF under the name Yellow (4502) (Chromalite); red-tinted mother-of-pearl with a gold sheen, notably marketed by BASF under the name Sunstone G012 (Gemtone); pink mother-of-pearl, notably marketed by BASF under the name Tan opale G005 (Gemtone); black mother-of-pearl with a gold sheen, notably marketed by BASF under the name Nu antique bronze 240 AB (Timica); blue mother-of-pearl, notably marketed by MERCK under the name Matte Blue (17433) (Microna); white mother-of-pearl with a silver sheen, notably marketed by MERCK under the name Xirona Silver; and orange-pink and golden-green mother-of-pearl, among others; marketed by the company MERCK under the name Indian Summer (Xirona) and their blends.

[0258] As further examples of nacres, we can also mention particles comprising a borosilicate substrate coated with titanium oxide.

[0259] Particles with a glass substrate coated with titanium oxide are notably sold under the name METASHINE MC1080RY by the company TOYAL.

[0260] Finally, examples of mother-of-pearl include polyethylene terephthalate flakes, particularly those marketed by Meadowbrook Inventions under the name Silver IP 0.004X0.004 (silver flakes). Multilayer pigments based on synthetic substrates such as alumina, silica, calcium sodium borosilicate or calcium aluminum borosilicate, and aluminum can also be considered.

[0261] Special effect pigments may also be selected from reflective particles, that is to say, particles whose size, structure, including the thickness of the layer(s) that constitute them and their physical and chemical nature, and surface condition, enable them to reflect incident light. This reflection may, where appropriate, have sufficient intensity to create, on the surface of the composition or mixture, when applied to the makeup support, highlights visible to the naked eye, that is to say, brighter points that contrast with their surroundings by appearing to shine.

[0262] Reflective particles can be selected so as not to significantly alter the coloring effect generated by the coloring agents associated with them, and more particularly so as to optimize this effect in terms of color rendering. They may, in particular, have a yellow, pink, red, bronze, orange, brown, gold and / or copper color or reflection.

[0263] These particles can have various shapes, including being platelet-shaped or globular, particularly spherical.

[0264] Reflective particles, whatever their shape, may or may not have a multilayer structure and, in the case of a multilayer structure, for example at least one layer of uniform thickness, in particular of a reflective material.

[0265] When reflective particles do not have a multilayer structure, they can be composed, for example, of metal oxides, in particular titanium or iron oxides obtained by synthesis.

[0266] When reflective particles have a multilayer structure, they may, for example, comprise a natural or synthetic substrate, in particular a synthetic substrate at least partially coated by at least one layer of a reflective material, in particular at least one metal or metallic material. The substrate may be monomaterial, multimaterial, organic and / or inorganic.

[0267] More specifically, it may be selected from glasses, ceramics, graphite, metal oxides, aluminas, silicas, silicates, in particular aluminosilicates and borosilicates, synthetic mica and mixtures thereof, this list not being exhaustive.

[0268] The reflective material may include a layer of metal or a metallic material.

[0269] Reflective particles are described in particular in documents JP-A-09188830, JP-A-10158450, JP-A-10158541, JP-A-07258460 and JP-A-05017710.

[0270] As further examples of reflective particles comprising a mineral substrate coated with a layer of metal, one can also mention particles comprising a borosilicate substrate coated with silver.

[0271] Silver-coated glass substrate particles in the form of wafers are sold under the name MICROGLASS METASHINE REFSX 2025 PS by the company TOYAL. Nickel / chromium / molybdenum alloy-coated glass substrate particles are sold under the names CRYSTAL STAR GF 550, GF 2525 by the same company.

[0272] Particles comprising a metallic substrate such as silver, aluminum, iron, chromium, nickel, molybdenum, gold, copper, zinc, tin, magnesium, steel, bronze, titanium may also be used, said substrate being coated with at least one layer of at least one metallic oxide such as titanium oxide, aluminum oxide, iron oxide, cerium oxide, chromium oxide, silicon oxides and mixtures thereof.

[0273] An example can be cited as aluminium, bronze or copper powders coated with SiO2 marketed under the name VISIONAIRE by the company ECKART.

[0274] Other examples include non-substrate interference pigments such as liquid crystals (Wacker's Helicones HC) and interference holographic glitter (Spectratek's Geometry Pigments or Spectra f / x). Special effect pigments also include fluorescent pigments, whether daylight fluorescent or ultraviolet fluorescent, phosphorescent pigments, photochromic pigments, thermochromic pigments, and quantum dots, marketed, for example, by Quantum Dots Corporation.

[0275] The variety of pigments that can be used in the present invention makes it possible to obtain a rich palette of colors, as well as particular optical effects such as metallic, interference effects.

[0276] The size of the pigment used in the composition according to the present invention is generally between 10 nm and 200 pm, preferably between 20 nm and 80 pm, and more preferably between 30 nm and 50 pm.

[0277] The pigments can be dispersed within the composition by means of a dispersing agent.

[0278] The dispersing agent serves to protect the dispersed particles from agglomeration or flocculation. This dispersing agent may be a surfactant, an oligomer, a polymer, or a mixture of several of these, possessing one or more functionalities with a strong affinity for the surface of the particles to be dispersed. In particular, they may adhere physically or chemically to the surface of the pigments. These dispersants also have at least one functional group that is compatible with or soluble in the continuous medium.In particular, esters of 12-hydroxystearic acid are used, especially C8 to C20 fatty acids and polyols such as glycerol, diglycerin, such as poly(12-hydroxystearic acid) stearate with a molecular weight of approximately 750g / mol such as that sold under the name Solsperse 21 000 by Avecia, polyglyceryl-2 dipolyhydroxystearate (name CTFA) sold under the reference Dehymyls PGPH by Henkel or polyhydroxystearic acid such as that sold under the reference Arlacel P100 by Uniqema and their mixtures.

[0279] As another dispersant that can be used in the compositions of the invention, we can mention quaternary ammonium derivatives of polycondensed fatty acids such as Solsperse 17 000 sold by Avecia, poly dimethylsiloxane / oxypropylene mixtures such as those sold by Dow Corning under the references DC2-5185, DC2-5225 C.

[0280] The pigments used in the composition can be surface treated with an organic agent.

[0281] Thus the pigments previously treated on the surface useful within the framework of the invention are pigments which have undergone totally or partially a surface treatment of a chemical, electronic, electro-chemical, mechano-chemical or mechanical nature, with an organic agent such as those described in particular in Cosmetics and Toiletries, February 1990, Vol. 105, p. 53-64 before being dispersed in the composition according to the invention.These organic agents may be chosen for example from waxes, for example carnauba wax and beeswax; fatty acids, fatty alcohols and their derivatives, such as stearic acid, hydroxystearic acid, stearyl alcohol, hydroxystearyl alcohol, lauric acid and their derivatives; 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 motifs; alkanoamines; compounds. silicones, for example silicones, in particular polydimethylsiloxanes; fluorinated organic compounds, for example perfluoroalkyl ethers; fluoro-silicone compounds.

[0282] The surface-treated pigments useful in the composition may also have been treated by a mixture of these compounds and / or have undergone several surface treatments.

[0283] The surface-treated pigments useful in the context of the present invention can be prepared using surface treatment techniques well known to those skilled in the art or found as such in the commercial market.

[0284] Preferably, the surface-treated pigments are covered by an organic layer.

[0285] The organic agent with which the pigments are treated can be deposited on the pigments by solvent evaporation, chemical reaction between the molecules of the surfactant or creation of a covalent bond between the surfactant and the pigments.

[0286] Surface treatment can thus be achieved, for example, by a chemical reaction of a surfactant with the surface of the pigments and the creation of a covalent bond between the surfactant and the pigments or fillers. This method is described in particular in US patent 4,578,266.

[0287] Preferably, an organic agent covalently linked to the pigments will be used.

[0288] The surface treatment agent may represent from 0.1 to 50% by weight of the total weight of the pigment treated on the surface, preferably from 0.5 to 30% by weight, and even more preferably from 1 to 20% by weight of the total weight of the pigment treated on the surface.

[0289] Preferably, the surface treatments of the pigments are chosen from the following treatments:

[0290] - a PEG-Silicone treatment such as the AQ surface treatment marketed by LCW;

[0291] - a Methicone treatment such as the SI surface treatment marketed by LCW;

[0292] - a Dimethicone treatment such as the Covasil 3.05 surface treatment marketed by LCW;

[0293] - a Dimethicone / Trimethylsiloxysilicate treatment as the surface treatment Covasil 4.05 marketed by LCW;

[0294] - a Magnesium Myristate treatment such as MM surface treatment marketed by LCW;

[0295] - an Aluminium Dimyristate treatment such as the MI surface treatment marketed by Miyoshi;

[0296] - a Perfluoropolymethylisopropyl ether treatment as a surface treatment FHC marketed by LCW;

[0297] - an Isostearyl Sebacate treatment such as the commercially available HS surface treatment by Miyoshi;

[0298] - a Perfluoroalkyl Phosphate treatment as a PF surface treatment marketed by Daito;

[0299] - an acrylate / dimethicone copolymer and perfluoalkyl phosphate treatment such as the FSA surface treatment marketed by Daito;

[0300] - a Polymethylhydrogen siloxane / Perfluoroalkyl Phosphate treatment such as the FS01 surface treatment marketed by Daito;

[0301] - an Acrylate / Dimethicone Copolymer treatment as the surface treatment ASC marketed by Daito;

[0302] - an Isopropyl Titanium Triisostearate treatment such as the ITT surface treatment marketed by Daito;

[0303] - an Acrylate copolymer treatment such as the APD surface treatment marketed by Daito;

[0304] - a Perfluoroalkyl Phosphate / Isopropyl Titanium Triisostearate treatment such as the PF + ITT surface treatment marketed by Daito.

[0305] According to a particular embodiment of the invention, the dispersing agent is present with organic or inorganic pigments in submicron-sized particulate form.

[0306] By "sub-micronic" or in English "sub-micronic" is meant pigments whose particle size has been micronized by micronization method and whose average particle size is less than one micrometer (pm), in particular between 0.1 and 0.9 pm, and preferably between 0.2 and 0.6 pm.

[0307] According to one embodiment, the dispersing agent and the pigment(s) are present in quantity (dispersing agent: pigment), according to a weight ratio, between 1:4 and 4:1, particularly between 1.5:3.5 and 3.5:1 or better between 1.75:3 and 3:1.

[0308] The dispersing agent(s) may therefore have a silicone skeleton, such as silicone polyether and amino-silicone dispersants. Suitable dispersing agents include:

[0309] - amino-silicones i.e. silicones comprising one or more amino groups such than those marketed under the names and references: BYK LPX 21879, by BYK, GP-4, GP-6, GP-344, GP-851, GP-965, GP-967 and GP-988-1, marketed by Genesee Polymers,

[0310] - silicone acrylates such as Tego ® RC 902, Tego ® RC 922, Tego ® RC 1041, and Tego ® RC 1043, marketed by Evonik,

[0311] - polydimethylsiloxane (PDMS) silicones with carboxylic groups such as X- 22162 and X-22370 by Shin-Etsu, silicone epoxy such as GP-29, GP-32, GP-502, GP-504, GP-514, GP-607, GP-682, and GP-695, by Genesee Polymers, or Tego ® RC 1401, Tego ® RC 1403, Tego ® RC 1412, by Evonik.

[0312] According to a particular embodiment, the dispersing agent(s) are of the amino-silicone type and are cationic.

[0313] Preferably, the pigment(s) is / are chosen from mineral, mixed mineral-organic or organic pigments.

[0314] In one embodiment of the invention, the pigment(s) are organic pigments, preferably organic pigments surface-treated with an organic agent selected from silicone compounds. In another embodiment of the invention, the pigment(s) are mineral pigments.

[0315] Preferably, the pigment(s) are chosen from iron oxides, in particular red, brown or black. An example of an iron oxide is the iron oxide sold by Sun Chemical under the name SunPuro® Red Iron Oxide.

[0316] Direct dye

[0317] Composition C used in the process according to the invention may include one or more direct dye(s).

[0318] By "direct dye," we mean natural and / or synthetic dyes, different from oxidation dyes. These are dyes that diffuse superficially onto the fiber. They can be ionic, for example cationic or anionic, or non-ionic.

[0319] Examples of suitable direct dyes that may be mentioned include azo direct dyes; (poly)methine dyes such as cyanines, hemicyanines and styryls; carbonyl dyes; azine dyes; nitro(hetero)aryl dyes; tri(hetero)arylmethane dyes; porphyrin dyes; phthalocyanine dyes and natural direct dyes, alone or in mixtures.

[0320] Direct dyes can be selected from anionic direct dyes. The anionic direct dyes of the invention are dyes commonly called "acid" direct dyes because of their affinity for alkali substances. Anionic direct dyes are understood to mean any direct dye having in its structure at least one CO2R or SO3R substituent, where R designates a hydrogen atom or a cation from a metal or an amine, or an ammonium ion. Anionic dyes can be selected from acidic nitro direct dyes, acidic azo dyes, acidic azinic dyes, acidic triarylmethanic dyes, acidic indoamine dyes, acidic anthraquinone dyes, indigoids, and acidic natural dyes.

[0321] A titre d’exemple de colorants acides on peut citer : Acid Red 1, Acid Red 4, Acid Red 13, Acid Red 14, Acid Red 18, Acid Red 27, Acid Red 28, Acid Red 32, Acid Red 33, Acid Red 35, Acid Red 37, Acid Red 40, Acid Red 41, Acid Red 42, Acid Red 44, Pigment red 57, Acid Red 68, Acid Red 73, Acid Red 135, Acid Red 138, Acid Red 184, Food Red 1, Food Red 13, Acid Orange 6, Acid Orange 7, Acid Orange 10, Acid Orange 19, Acid Orange 20, Acid Orange 24, Yellow 6, Acid Yellow 9, Acid Yellow 36, Acid Yellow 199, Food Yellow 3; Acid Violet 7, Acid Violet 14, Acid Blue 113, Acid Blue 117, Acid Black 1, Acid Brown 4, Acid Brown 20, Acid Black 26, Acid Black 52, Food Black 1, Food Black 2 ; Food yellow 3 ou sunset yellow; Acid Red 111, Acid Red 134, Acid yellow 38 ;

[0322] A titre d’exemple de colorants azo anioniques pyrazolones on peut citer : Acid Red 195, Acid Yellow 23, Acid Yellow 27, Acid Yellow 76Acid Yellow 17 ;

[0323] As an example of anthraquinone dyes, we can cite: Acid Blue 25, Acid Blue 43, Acid Blue 62, Acid Blue 78, Acid Blue 129, Acid Blue 138, Acid Blue 140, Acid Blue 251, Acid Green 25, Acid Green 41, Acid Violet 42, Acid Violet 43, Mordant Red 3; EXT purple No. 2;: Acid Black 48;

[0324] Examples of nitro dyes include: Acid Brown 13; Acid Orange 3; examples of dyes of formula (XXII') include: Acid Yellow 1, Sodium salt of 2,4-dinitro-1-naphthol-7-sulfonic acid, 2-piperidino-5-nitrobenzenesulfonic acid, 2(4'-N,N(2'-hydroxyethyl)amino-2'-nitro)aniline ethanesulfonic acid, 4-[3-hydroxyethylamino-3-nitrobenzenesulfonic acid; EXT D&C yellow 7;

[0325] Examples of triarylmethane dyes include: Acid Blue 1; Acid Blue 3; Acid Blue 7, Acid Blue 9; Acid Violet 49; Acid green 3; Acid green 5; Acid Green 50.

[0326] Examples of xanthenic dyes include: Acid Yellow 73; Acid Red 51; Acid Red 52, Acid Red 87; Acid Red 92; Acid Red 95; Acid Violet 9.

[0327] Examples of indole dyes include: Acid Blue 74;

[0328] Examples of quinoline dyes include: Acid Yellow 2, Acid Yellow 3 and Acid Yellow 5.

[0329] Among the natural direct dyes that can be used according to the invention are lawsone, juglone, alizarin, purpurin, carminic acid, kermesic acid, purpurogallin, protocatechaldehyde, indigo, isatin, curcumin, spinulosin, apigenidine, and orceins. Extracts or decoctions containing these natural dyes, and in particular henna-based poultices or extracts, can also be used.

[0330] The coloring agent(s) may be present in a total quantity ranging from 0.001 to 20% by weight, preferably from 0.005 to 15% by weight relative to the total weight of composition C, preferably the coloring agent(s) are chosen from pigments.

[0331] The pigment(s) may be present in a total quantity ranging from 0.05 to 20% by weight, preferably from 0.1 to 15% by weight, better from 0.5 to 10% by weight relative to the total weight of composition C.

[0332] The direct colorant(s) may be present in a total quantity ranging from 0.001 to 10% by weight, preferably from 0.005 to 5% by weight relative to the total weight of composition C. Associative polymers

[0333] The composition C used in the process according to the invention may further comprise at least one associative polymer different from the polymer comprising at least one reactive group selected from the carboxylic acids as defined above.

[0334] As mentioned above, "associative polymers" are polymers capable, in an aqueous medium, of reversibly associating with each other or with other molecules.

[0335] Their chemical structure includes more particularly at least one hydrophilic zone and at least one hydrophobic zone.

[0336] By "hydrophobic group" is meant a radical or hydrocarbon chain polymer, saturated or unsaturated, linear or branched, comprising at least 10 carbon atoms, preferably from 10 to 30 carbon atoms, in particular from 12 to 30 carbon atoms and more preferably from 18 to 30 carbon atoms.

[0337] The associative polymers may be non-ionic, anionic, cationic, or amphoteric. Preferably, the associative polymer(s) are chosen from anionic associative polymers.

[0338] Among the associative anionic polymers, we can cite copolymers comprising among their monomers an α,[3-monoethylenic unsaturation carboxylic acid and an ester of an α,[3-monoethylenic unsaturation carboxylic acid and an oxyalkylated fatty alcohol.

[0339] Preferably these compounds also comprise as a monomer an ester of α,[3-monoethylenic unsaturation carboxylic acid and C1-C4 alcohol.

[0340] As an example of this type of compound, we can cite ACULYN 22® sold by ROHM and HAAS, which is a methacrylic acid / ethyl acrylate / oxyalkylated stearyl methacrylate terpolymer, as well as ACULYN 88 also sold by ROHM and HAAS.

[0341] Preferably, the associative polymer(s), different from polymers comprising at least one reactive group selected from the carboxylic acids previously described, are chosen from copolymers comprising among their monomers an α,[3-monoethylenic unsaturated carboxylic acid and an ester of an α,[3-monoethylenic unsaturated carboxylic acid and an oxyalkylated fatty alcohol.

[0342] Advantageously, the total content of the associative polymer(s) other than the polymer(s) comprising at least one reactive group selected from the carboxylic acids as defined above ranges from 0.05 to 15% by weight, preferably from 0.05 to 10% by weight, more preferably from 0.1 to 5% by weight, and even more preferably from 0.1 to 1% by weight relative to the total weight of composition C. Organic solvents

[0343] Composition C used in the process according to the invention may comprise one or more organic solvents.

[0344] Examples of organic solvents include lower C1-C4 alkanols such as ethanol and isopropanol; polyols and polyol ethers such as 2-butoxyethanol, 1,2-hexanediol, propylene glycol, pentylene glycol, propylene glycol monomethyl ether, diethylene glycol monoethyl ether and monomethyl ether, as well as aromatic alcohols, in particular aromatic monoalcohols such as benzyl alcohol, phenoxyethanol, and mixtures thereof.

[0345] Organic solvents may be present in a total content of between 10 and 80% by weight, preferably between 25 and 70% by weight and more preferably between 35 and 65% by weight relative to the total weight of composition C.

[0346] Composition C used in the process according to the invention may be aqueous. The water content may range from 1 to 90% by weight, preferably from 10 to 80% by weight, more preferably from 20 to 70% by weight relative to the total weight of composition C. Additives

[0347] Composition C used in the process according to the invention may contain any adjuvant or additive usually used.

[0348] Among the additives that may be contained in the composition, we can mention reducing agents, softeners, antifoaming agents, moisturizing agents, clays, mineral fillers, UV filters, peptizers, perfumes, anionic, cationic, non-ionic or amphoteric surfactants, proteins, vitamins, polymers other than the polymers previously described, preservatives, amino and / or non-amino silicones, oils, waxes other than silicones in wax form, and mixtures thereof.

[0349] The composition C used in the process according to the invention may be in particular in the form of a suspension, dispersion, gel, emulsion, in particular an oil-in-water (O / W) or water-in-oil (W / O) emulsion, or multiple (W / O / E or polyol / H / E or H / E / H), in the form of cream, foam, stick, vesicle dispersion, including ionic or non-ionic lipids, biphasic or multiphase lotion.

[0350] A person skilled in the art will be able to choose the appropriate pharmaceutical form, as well as its method of preparation, on the basis of their general knowledge, taking into account on the one hand the nature of the constituents used, in particular their solubility in the support, and on the other hand the application envisaged for the composition.

[0351] The above additives may generally be present in quantities of each of them between 0 and 20% by weight, relative to the total weight of composition C. Process

[0352] Exposure of hair to UV radiation, as defined above, can be carried out on dry or wet hair, as well as on all types of hair, light or dark, natural or colored, permed, bleached or straightened.

[0353] Exposure of hair to UV radiation can be achieved using a device selected from UV lamps, UV clamps such as those described in ...

[0354] This exposure may consist of illumination of the hair with ambient light or with an artificial light source. The ambient or artificial light must emit radiation in the UV range, with a proportion of UV radiation of at least 2% of the total irradiance of the light used, for example with a lamp, flash, laser, LEDs, for example in the form of an LED array. The wavelength of the emitted light is preferably centered on 365 nm, in particular between 100 nm and 500 nm, and better between 200 nm and 420 nm. Preferably, it will be an artificial light source emitting an energy between 0.5 and 5 W / cm2, with exposure times adapted accordingly, the lighting system can produce a luminous intensity of, for example, between 500 mJ / cm2 and 60 J / cm2, preferably between 2 J / cm2 and 40 J / cm2.

[0355] Exposure to UV radiation is generally carried out for a period of 5 seconds to 3 hours, preferably for a period of at least 10 seconds up to a period less than or equal to 30 minutes.

[0356] Exposure of hair to UV radiation can be carried out between 15 and 40°C.

[0357] According to a first embodiment, step a) is followed by step b).

[0358] In this embodiment, after exposing the hair to UV radiation, one can wait between 1 minute and 1 hour, preferably between 1 minute and 30 minutes, before applying composition C to the hair.

[0359] Composition C described above can be applied to dry or damp hair. If UV exposure is carried out on dry hair, it may be considered to wet the hair before applying Composition C. According to a particular embodiment, Composition C is applied to dry hair.

[0360] Preferably, a drying step is implemented after the application of composition C to the hair.

[0361] Application to the hair can be carried out by any conventional means, in particular by means of a comb, a brush, a sponge or the fingers.

[0362] The application of composition C to the hair is generally carried out at room temperature (between 15 and 25 °C).

[0363] Hair drying after application of hair colour composition C can be achieved by allowing the hair to dry or by blow-drying the hair.

[0364] This drying step can be carried out using a helmet, a hair dryer, a climazon, preferably using a hair dryer.

[0365] The process according to the invention can thus include a step of applying heat to the keratin fibers using a heating tool.

[0366] The heat application step of the process of the invention can be carried out using a helmet, a hair dryer, a straightening or curling iron, a climazon, etc. Preferably, the heat application step of the process of the invention is carried out using a hair dryer.

[0367] During the heat application step on the hair, a mechanical action on the strands can be exerted such as combing, brushing, passing with fingers.

[0368] When the step of applying heat to the hair is carried out using a helmet or a hair dryer, the temperature is preferably between 30 and 110°C, preferably between 50 and 90°C.

[0369] Preferably, if the hair is dried, it is dried not only with heat but also with an airflow. This airflow during drying helps to improve the individualization of the coating.

[0370] According to a second embodiment, step a) is carried out after step b).

[0371] In this embodiment, the exposure of the hair to UV radiation is therefore carried out after the application of composition C.

[0372] According to this operating procedure, it is possible to wait between 1 minute and 2 hours between the application of composition C and the exposure of the hair to UV radiation.

[0373] Preferably, the exposure time is between 1 minute and 30 minutes between the application of composition C and the exposure of the hair to UV radiation.

[0374] Preferably, a drying step is implemented after the application of composition C to the hair and before exposing the hair to UV radiation.

[0375] Hair drying after application of hair coloring composition C can be carried out in the same way as detailed above in the first embodiment.

[0376] Preferably, according to a first embodiment, the invention is a hair coloring process comprising the following steps: i) exposure of the hair to UV radiation; then ii) optionally a step of washing, rinsing or wringing said hair; then

[0377] (iii) the application to the hair of at least one composition C comprising:

[0378] - at least one (poly)carbodiimide compound as described above;

[0379] - at least one polymer comprising at least one reactive group selected from the carboxylic acids; and

[0380] - at least one coloring agent selected from pigments, direct colorants, and their mixtures; then (iv) optionally a step of washing, rinsing, wringing and / or drying the hair.

[0381] According to a preferred embodiment, exposure to UV radiation is carried out on dry hair.

[0382] Preferably, composition C further comprises at least one associative polymer as described above, different from the polymer comprising at least one reactive group selected from carboxylic acids as defined above.

[0383] Advantageously, in the coloring process according to the invention, step b) consists of extemporaneously mixing at least two compositions A and B at the time of use to obtain a hair coloring composition C and applying composition C to the hair, with:

[0384] - composition A comprising at least one (poly)carbodiimide compound such that defined previously;

[0385] - composition B comprising at least one polymer comprising at least one reactive group chosen from among the carboxylic acids as defined previously,

[0386] composition A and / or composition B comprising at least one colouring agent as defined above.

[0387] More preferably, in the coloring process according to the invention, step b) consists of extemporaneously mixing at least two compositions A and B at the time of use to obtain a hair coloring composition C and applying the hair coloring composition C to the hair, with:

[0388] - composition A comprising at least one (poly)carbodiimide compound such that defined previously;

[0389] - composition B comprising at least one coloring agent as defined previously, and at least one polymer comprising at least one reactive group selected from the carboxylic acids as defined previously.

[0390] According to a first embodiment, the coloring process according to the invention is a hair coloring process comprising:

[0391] (i) exposure of the hair to UV radiation; then

[0392] (ii) a step consisting of extemporaneously mixing at least two compositions A and B at the time of use to obtain a composition C and applying composition C to the hair, with:

[0393] - composition A comprising at least one (poly)carbodiimide compound such that defined previously;

[0394] - composition B comprising at least one coloring agent as defined previously and at least one polymer comprising at least one reactive group selected from the carboxylic acids as defined previously; then

[0395] (iii) optionally a step of washing, rinsing, wringing and / or drying the hair.

[0396] Preferably, the polymer comprising at least one reactive group selected from carboxylic acids is selected from acrylic polymers.

[0397] Preferably, composition A does not include a coloring agent as defined above.

[0398] According to this embodiment, compositions A and B are mixed preferably less than 15 minutes before application to the hair, more preferably less than 10 minutes before application, better less than 5 minutes before application.

[0399] The weight ratio between composition A and composition B is preferably from 0.1 to 10, preferably from 0.2 to 5, better from 0.5 to 2, or even from 0.6 to 1.5. In a particular embodiment, the weight ratio between composition A and composition B is equal to 1.

[0400] The total quantity of the (poly)carbodiimide compound(s) preferably ranges from 0.01 to 40% by weight, more preferably from 0.1 to 30% by weight, better from 0.5 to 20% by weight, even more preferably from 1 to 15% by weight relative to the total weight of composition A.

[0401] The total quantity of the polymer(s) comprising at least one reactive group selected from the carboxylic acids is preferably from 0.2 to 60% by weight, more preferably from 1 to 50% by weight, better still from 1 to 40% by weight, and even more preferably from 2 to 30% by weight relative to the total weight of composition B.

[0402] According to a particular embodiment, composition B comprises at least one associative polymer as defined above. The total content of the associative polymer(s) preferably ranges from 0.05 to 15% by weight, preferably from 0.05 to 10% by weight, more preferably from 0.1 to 5% by weight, and even more preferably from 0.1 to 1% by weight relative to the total weight of composition B.

[0403] According to a second embodiment, the invention is a hair coloring process comprising the following steps: (i) the application to the hair of at least one composition C comprising:

[0404] - at least one (poly)carbodiimide compound as described above;

[0405] - at least one polymer comprising at least one reactive group selected from the carboxylic acids; and

[0406] - at least one coloring agent selected from pigments, direct colorants, and their mixtures; then (ii) optionally a step of washing, rinsing, wringing the hair,

[0407] (iii) a step of drying the hair; then

[0408] (iv) exposure of the hair to UV radiation.

[0409] Preferably, the same embodiments as those described in the first embodiment also apply in the second embodiment.

[0410] The present invention will now be described more specifically by means of examples, which are in no way limiting to the scope of the invention. However, the examples allow for the support of specific features, variants, and preferred embodiments of the invention. EXAMPLES

[0411] The (poly)carbodiimide(s) of the invention are accessible by synthetic methods known to those skilled in the art, from commercial products or from reagents synthesizable according to chemical reactions also known to those skilled in the art. Examples include the book *Sciences of Synthesis - Houben - Weyl Methods of Molecular Transformations*, 2005, Georg Thiem Verlag Kg, Rudigerstrasse 14, D-70469 Stuttgart, or US patent 4,284,730 or Canadian application CA 2,509,861.

[0412] More particularly, the process for preparing the (poly)carbodiimides of the invention uses in a first step a diisocyanate reagent (1): O=C=N-LrN=C=O (1), formula (1) in which Li is as defined above, which reacts in the presence of a carboimidation catalyst (2) such as those described in US 4,284,730, in particular phosphorus catalysts particularly chosen from among phospholene oxides and phospholene sulfoxides, diaza and oxazaphospholanes, preferably under an inert atmosphere (nitrogen or Argon), and in particular in a polar solvent, preferably aprotic, such as THF, glyme, diglyme, 1,4-dioxane, and DMF, at a temperature between ambient temperature and solvent reflux, preferably around 140 °C; to lead to the carbodiimide diisocyanate compound (3): O=C=N-L1-(N=C=N-L1)nN=C=O (3), formula (3) in which Li and n are as defined previously. Benzoyl halogen such as benzoyl chloride may be added to deactivate the catalyst.

[0413] To obtain "symmetrical" (poly)carbodiimides, in the second step of the preparation process, compound (3) reacts with 1 molar equivalent (1 eq) of nucleophilic reagent Ri-XrH, then with 0.5 eq of HEH reagent with Rb Xi and E as defined previously, to give the "symmetrical" compound according to the invention (4): [R1-X1-C(O)-NH-L1-(N=C=N-L1)n-NH-C(O)]2-E (4), formula (4) in which Rh Xb n, and E are as defined previously. According to one variant to obtain compound (4) from (3) it is possible to first add 0.5 eq. of HEH reagent, then 1 eq. of Ri-XrH reagent.

[0414] To obtain "asymmetric" (poly)carbodiimides, in the second step of the preparation process, compound (3) reacts with 1 molar equivalent (1 eq) of nucleophilic reagent RrXi-H and then 1 eq. of HEH reagent with Rb Xi and E as defined above, to give the compound (5): R1-X1-C(O)-NH-L1-(N=C=N-L1)n-NH-C(O)-EH (5), formula (5) in which Rh Xb Lb n, and E are as defined above.

[0415] According to a variant for obtaining compound (5) from (3) it is possible to add first 1 eq. of reagent Ri-XrH, then 0.5 eq. of reagent HEH.

[0416] In a third step, compound (5) reacts with 1 eq. of compound (6) R2-X2-C(O)-NH-Li-(N=C=N-Li)zN=C=O (6), said compound (6) is prepared beforehand from compound (3' ): O=C=N-L1-(N=C=N-L1)ZN=C=O (3'),

[0417] formula (3') in which Li and z are as defined previously which reacts with 1 eq of nucleophilic reagent R2-X2-H with Lb R2, X2, and z as defined previously, to give rise to the asymmetric compound (7): R1-X1-C(O)-NH-L1-(N=C=N-L1)n-NH-C(O)-EC(O)-NH-L1-(N=C=N-L1)z-NH-C(O)-X2-R2 (7),

[0418] Formula (7) in which Rb Xb Lb R2, X2, n, z and E are as defined previously.

[0419] It is also possible to react 1 molar equivalent of compound O=C=N-Lr (N=C=N-Li)zN=C=O (3') with 1 / w molar equivalent of HEH, then 1 eq. of nucleophilic reagent R2-X2-H to give compound (8): H-CE-QOj-NH-LrtN^N-LÛX-NH-QOj-Xz-RaS),

[0420] formula (8) in which Lb R2, X2, z and E are as defined previously, and w is an integer from 1 to 3, more preferably w = 1.

[0421] This latter compound (8) can then react with 1 eq of compound (4'): Ri-Xi-C(O)-NH-Li-(N=C=N-Li)nN=C=O (4'), (said compound (4') being able to be synthesized by reaction of 0.5 eq. of nucleophilic reagent Ri-XrH with 1 equivalent of compound (3)), to give rise to the (poly)carbodiimide of the invention (9): R1-X1-C(O)-NH-L1-(N=C=N-L1)n-NH-C(O)-[EC(O)-NH-L1-(N=C=N-L1)z]w-NH C(O)-X2-R2 (9), formula (9) in which Lb Rb Xb R2, X2, n, z, w, and E are as defined above.

[0422] (Poly)carbodiimide compounds, as well as all reaction intermediates and reactants, can be purified with conventional methods known to those skilled in the art, such as extraction with water and water-immiscible organic solvent, precipitation, centrifugation, filtration, and / or chromatography.

[0423] Example 1: Process for the synthesis of the (poly)carbodiimide compound

[0424] In a 500 mL three-necked flask equipped with a thermometer, a stirrer and a reflux tube, 50 g of dicyclohexylmethane 4,4'-diisocyanate and 0.5 g of 4,5-dihydro-3-methyl-l-phenyl-lH-phosphole 1-oxide were introduced under stirring.

[0425] The reaction medium was heated to 140°C under nitrogen for 4 hours, following the reaction by infrared spectroscopy through the absorption of isocyanate functions between 2200 and 2300 cm1, then cooled to 120°C.

[0426] A mixture of 5.3 g of polyethylene glycol monomethyl ether and 1.2 g of 1,4-butanediol is introduced into the reaction medium while stirring. The temperature of 120°C is maintained until the complete disappearance of the isocyanate groups, monitored by infrared spectroscopy at 2200-2300 cm1, and then cooled to room temperature.

[0427] After cooling to room temperature, the reaction mixture is poured dropwise under vigorous stirring into a 500 mL glass beaker containing 85 g of distilled water to produce the desired product in the form of a translucent yellow liquid. Example 2

[0428] Compositions A and B as described in Tables 1 and 2 below were prepared: quantities are expressed in g of raw material as is / 100 g, unless otherwise stated. Thus, quantities may be expressed in g of active substance (a) / 100 g.

[0429] [Tables 1] Composition A Polycarbodiimide (1) 17.5 Ethanol Qsp 100

[0430] (1) synthesized according to the synthesis process described in Example 1 (at 40% of matter active in water).

[0431] [Tableaux2] Composition B Acrylates copolymer (2) 29.2 Red iron oxide 12 Divinyldimethicone / Dimethicone copolymer (3) (and) C12-13 Pareth-3 (and) Ci2-b Pareth-23 10.2 Amodimethicone 3 Acrylates / Steareth-20 methacrylate copolymer (4) 2.2 Water, preservative, solvents q.s. 100

[0432] (2) sold by the company DAITO KASEI KOGYO under the trade name DAITOSOL 3000SLPN-PE1 (aqueous dispersion with 30% active ingredient);

[0433] (3) sold by Dow Corning under the trade name DOW CORNING HMW 2220 NON-IONIC EMULSION (Divinyldimethicone / dimethicone block copolymer in aqueous emulsion) (with 60% active material));

[0434] (4) sold by the company ROHM and HAAS under the trade name ACULYN 22® (methacrylic acid / ethyl acrylate / oxyalkylated stearyl methacrylate terpolymer with 30% active material).

[0435] Composition A was then mixed with composition B at a mass ratio of 50 / 50 to obtain composition C according to the invention. Protocols

[0436] Several application methods have been used.

[0437] * According to the first method, composition C was applied with a finger to strands Natural, dry hair that was 90% white was used at a concentration of 0.8 g of the product per gram of hair strand. The hair strands were then detangled and blow-dried. During this initial process, the hair strands were not exposed to any UV radiation.

[0438] This process is therefore a comparative process, hereinafter referred to as process PL

[0439] * According to another process, strands of dry, natural hair that are 90% white have First, the samples were exposed to UVA radiation for 60 minutes using a UV lamp (energy exposure: 213 mJ / cm² / min; wavelength: 365 nm). Then, composition C was applied under the same conditions as for the PL process.

[0440] This process is a process according to the invention, hereinafter referred to as process P260.

[0441] The P2i80 process according to the invention differs from the P220 process only in the period of exposure of the hair strands to UVA radiation. In the P2i80 process, strands of dry, natural, 90% white hair were first exposed to UVA radiation for 180 minutes.

[0442] * According to another process, strands of natural dry hair that are 90% white have First, the samples were exposed to UVB radiation for 20 minutes using a UV lamp (energy exposure: 149 mJ / cm² / min; wavelength: 305 nm). Then, composition C was applied under the same conditions as for the PL process.

[0443] This process is a process according to the invention, hereinafter referred to as process P320.

[0444] The P330 process according to the invention differs from the P320 process only in the period of exposure of the hair strands to UVB radiation. In the P330 process, strands of natural, 90% white, dry hair were first exposed to UVB radiation for 30 minutes.

[0445] The P360 process according to the invention differs from the P320 process only in the period of exposure of the hair strands to UVB radiation. In the P360 process, the strands of natural, 90% white, dry hair were first exposed to UVB radiation for 60 minutes.

[0446] The P3i80 process according to the invention differs from the P320 process only in the period of exposure of the hair strands to UVB radiation. In the P3i80 process, strands of natural, 90% white, dry hair were first exposed to UVB radiation for 180 minutes.

[0447] * According to another process, strands of natural dry hair that are 90% white have all were first exposed to UVC radiation for 20 minutes with a UV lamp (energy exposure: 294 mJ / cm2 / min; wavelength: 250 nm).

[0448] This process is a process according to the invention, hereinafter referred to as process P420.

[0449] The P430 process according to the invention differs from the P420 process only in the period of exposure of the hair strands to UVC radiation. In the P430 process, strands of dry, natural, 90% white hair were first exposed to UVC radiation for 30 minutes.

[0450] The P460 process according to the invention differs from the P420 process only in the period of exposure of the hair strands to UVC radiation. In the P460 process, strands of dry, natural, 90% white hair were first exposed to UVC radiation for 60 minutes.

[0451] The P4i80 process according to the invention differs from the P420 process only in the period of exposure of the hair strands to UVC radiation. In the P4i80 process, The strands of natural dry hair, 90% white, were first exposed to UVC radiation for 180 minutes.

[0452] * According to another method, composition C was applied with a finger to strands 90% natural dry hair was treated with a white powder at a concentration of 0.8g of the product per gram of hair strand. The hair strands were then detangled and blow-dried.

[0453] Then, the hair strands were exposed to UVA radiation for 30 minutes with a UV lamp (energy exposure: 213 mJ / cm2 / min; wavelength: 365 nm).

[0454] This process is therefore a process according to the invention, hereinafter referred to as process P5.

[0455] The P6 process according to the invention differs from the P5 process only in the type of radiation. In the P6 process, the hair strands were exposed to UVB radiation for 30 minutes with a UV lamp (energy exposure: 149 mJ / cm2 / min; wavelength: 305 nm).

[0456] The P7 process according to the invention differs from the P5 process only in the type of radiation. In the P7 process, the hair strands were exposed to UVC radiation for 30 minutes with a UV lamp (energy exposure: 294 mJ / cm2 / min; wavelength: 250 nm).

[0457] Following all these procedures, the hair strands were stored at room temperature for 3 hours.

[0458] The processes applied are summarized in Table 3 below:

[0459] [Tables3] Processes Application of steps Type of radiation Period of exposure to UV radiation (min) PI Step b) - - P26o Step a) then step b) UVA 60 P218o Step a) then step b) UVA 180 P320 Step a) then step b) UVB 20 P33o Step a) then step b) UVB 30 P3eo Step a) then step b) UVB 60 P3180 Step a) then step b) UVB 180 P420 Step a) then step b) UVC 20 P41o Step a) then step b) UVC 30 P46o Step a) then step b) UVC 60 P4180 Step a) then step b) UVC 180 P5 Step b) then step a) UVA 30 P6 Step b) then step a) UVB 30 P7 Step b) then step a) UVC 30

[0460] The different strands of hair treated by the PI to P7 processes were then subjected to a test of several repeated shampoos in order to evaluate the tenacity (the persistence) of the color obtained with the shampoos, according to the shampoo protocol described below. Shampoo Protocol#:

[0461] The colored hair strands are combed, moistened under water at 35°C before being passed between the fingers 5 times for 5 seconds. The hair strands are then squeezed dry between two fingers.

[0462] A standard shampoo (Garnier Ultra Doux) is applied evenly to the colored strands at a rate of 0.4g of standard shampoo per gram of strands, gently massaging the strands of hair along their length (6 passes) for 15 seconds, from root to tip.

[0463] The strands of hair are then placed in a watch glass and left to rest for 1 minute.

[0464] Next, the hair strands are rinsed with water by passing the strand between the fingers (15 passes). The hair strands are then squeezed dry between two fingers before the next shampoo.

[0465] Once the tests of several shampoos have been carried out, the strands of hair are combed and blow-dried. Results

[0466] The persistence of the color of the highlights was evaluated in the CIE L*a*b* system, using a Konica Minolta CM3600A spectrophotometer (illuminant D65, angle 10°, specular component included).

[0467] In this L*a*b* system, L* represents the intensity of the color, a* indicates the green / red color axis and b* the blue / yellow color axis.

[0468] The permanence of the color is evaluated by the color difference AE between measurements taken on colored strands before shampooing, and then after 5 shampoos according to the protocol described above. The lower the AE value, the more the color remains after shampooing.

[0469] The value of AE is calculated according to the following equation:

[0470] In this equation, L*, a*, b* represent the values ​​measured after hair coloring and after shampooing, and Lo*, a0*, b0* represent the values ​​measured after hair coloring but before shampooing.

[0471] The results are summarized in Table 4 below.

[0472] [Tables4] Processes Number of shampoos L* a* b* AE PI (comparative) 0 33.0 26.6 19.9 5 43.2 17.4 14.0 14.9 P26o (invention) 0 32.1 26.8 20.2 5 38.4 21.0 15.7 9.7 P2i8o (invention) 0 32.2 26.3 19.8 5 37.9 23.2 17.3 6.9 P32o (invention) 0 32.2 26.6 20.0 5 38.0 21.7 16.4 8.4 P33o (invention) 0 32.5 25.8 19.4 5 36.9 22.4 16.5 6.3 P36o (invention) 0 32.2 25.2 19.1 5 38.7 21.2 16.3 8.1 P3i8o (invention) 0 33.5 26.3 20.0 5 38.1 22.2 17.2 6.8 P42o (invention) 0 32.0 24.9 18.8 5 35.7 23.3 17.6 4.2 P430 (invention) 0 32.4 24.1 18.2 5 35.8 25.0 18.6 3.5 P46o (invention) 0 32.3 26.8 20.3 5 34.3 25.7 19.5 2.4 P4i8o (invention) 0 32.3 25.6 20.0 5 37.7 21.6 17.6 7.1 P5 (invention) 0 33.0 26.6 19.9 5 38.1 21.5 15.8 8.3 P6 (invention) 0 33.0 26.6 19.9 5 36.4 23.7 17.3 5.2 P7 (invention) 0 33.0 26.6 19.9 5 35.5 24.1 18.0 4.0

[0473] Hair strands treated with the processes according to the invention and washed with five shampoos exhibit lower AE values ​​than those of hair strands treated with the comparative PI process.

[0474] Thus, the coloured coating obtained with the process according to the invention exhibits improved resistance to shampoos.

Claims

Demands

1. A hair coloring process comprising: a) exposing the hair to UV radiation; and b) applying to the hair at least one composition C comprising: - at least one (poly)carbodiimide compound; - at least one polymer comprising at least one reactive group selected from carboxylic acids; and - at least one coloring agent selected from pigments, direct dyes, and mixtures thereof.

2. A method according to claim 1, characterized in that the exposure of the hair to said UV radiation, during step a), lasts for a period of at least 5 seconds, preferably for a period ranging from 10 seconds to 3 hours, more preferably from 50 seconds to 3 hours.

3. A method according to claim 1 or 2, characterized in that the UV radiation is selected from UVB radiation with a wavelength of 280 to 315 nm and UVC radiation with a wavelength of 100 to 280 nm, preferably UVC radiation with a wavelength of 100 to 280 nm.

4. A method according to any one of the preceding claims, characterized in that step a) is followed by step b) or step b) is followed by step a).

5. A process according to any one of the preceding claims, characterized in that the (poly)carbodiimide compound(s) is / are selected from the compounds of the following formula (I): O o ® A-*---R? HLUH in which: - Xi and X2 represent, independently, an oxygen atom O, a sulfur atom S, or an NH group; - Ri and R2 represent, independently, a group selected from a hydrocarbon radical, preferably alkyl, optionally interrupted by one or more heteroatoms, a group selected from the alkoxysilyl, hydroxysilyl,

6. acetoxysilyl, vinylsilyl, acrylalkylsilyl, methacrylalkylsilyl, crotonylalkylsilyl, carboxyanhydridoalkylsilyl, carboxyalkylsilyl, hydroxyalkylsilyl, aldehydoalkylsilyl, mercaptoalkylsilyl, norbornenylsilyl, acylpentadienylalkylsilyl, maleimidoalkylsilyl, sulfonylmylsilyl, (meth)acrylalkyl, crotonylalkyl, alkyl epoxide such as propyl epoxide or butyl epoxide, and azacyclopropane, and a hydrocarbon radical, preferably alkyl, optionally interrupted by one or more heteroatoms and by one or more groups selected from the alkoxysilyl, hydroxysilyl, acetoxysilyl, vinylsilyl, acrylalkylsilyl, methacrylalkylsilyl groups, crotonylalkylsilyl, carboxyanhydridoalkylsilyl, carboxyalkylsilyl, hydroxyalkylsilyl, aldehyde alkylsilyl, mercaptoalkylsilyl, norbornenylsilyl, acylpentadienylalkylsilyl, maleimidoalkylsilyl, sulfonylmylsilyl, (meth)acrylalkyl, crotonylalkyl, alkyl epoxide such as propyl epoxide or butyl epoxide,and azacyclopropane; - n denotes an integer ranging from 1 to 1000; and - A is a monomer chosen from the compounds below: A process according to any one of claims 1 to 4, characterized in that the (poly)carbodiimide compound(s) is / are chosen from the compounds of the following formula (II): v (H), Ouch A AH . jA ■'. "• .AA ' ' A\ K:? 'A TO .. XK < aAjH ... Nr s X< in which - Xi and X2 independently represent an oxygen atom O, a sulfur atom S, or an NH group; - Ri and R2 independently represent a hydrocarbon radical possibly interrupted by one or more heteroatom(s); - n and z denote an integer from 1 to 20, with n+z > 2, and w denotes an integer from 1 to 3; - Li independently represents a divalent aliphatic hydrocarbon radical in the C1-C18 group, a cycloalkylene radical in the C3-C15 group, a heterocycloalkylene group in the C3-C12 group, or an arylene group in the C6-C14 group, and mixtures thereof; - E independently represents a group chosen from: -O-R3-O-; -S-R4-S-; -R5-N(R6)-R4-N(R6)-R5-, in which R3 and R4 independently represent a divalent hydrocarbon radical possibly interrupted by one or more heteroatom(s); - R5 independently represents a covalent bond or a divalent saturated hydrocarbon radical, possibly interrupted by one or more heteroatom(s);- R6 independently represents a hydrogen atom, or a hydrocarbon radical possibly interrupted by one or more heteroatom(s).

7. A process according to claim 6, characterized in that the (poly)carbodiimide compound(s) is / are chosen from compounds of formula (II) in which: - Xi and X2 independently represent an oxygen atom; - Ri and R2 are chosen independently from dialkylaminoalcohols, alkyl esters of hydroxycarboxylic acid and monoalkyl ethers of (poly)alkylene glycol, in which a hydroxy group has been removed, and mixtures thereof; - n and z denote an integer from 1 to 20, with n+z > 2 and w equals 1; - L1 is chosen from a divalent aliphatic hydrocarbon radical in C1-C18, a cycloalkylene radical in C3-Ci5, a heterocycloalkylene group in C3-C12, or an arylene group in C6-Ci4, and mixtures thereof; - E independently represents a group chosen from: - -O-R3-O-; -S-R4-S-; -R5-N(R6)-R4-N(R6)-R5-; in which R3 and R4 are independently chosen from a C6-Ci4 arylene radical, a C3-C12 cycloalkylene radical, a linear or branched CrCi8 alkylene radical, possibly interrupted by one or more heteroatom(s), and mixtures thereof;- when R5 is not a covalent bond, R5 is chosen from a C6-Ci4 arylene radical, a C3-C12 cycloalkylene radical, a linear or branched Ci-Ci8 alkylene radical, possibly interrupted by one or more heteroatoms, and mixtures thereof; and - R6 is chosen from a C6-Ci4 arylene radical, a C3-C12 cycloalkylene radical, a linear or branched Ci-Ci8 alkylene radical, possibly interrupted by one or more heteroatoms, and mixtures thereof.

8. A process according to claim 6 or 7, characterized in that the (poly)carbodihnide compound(s) is / are selected from compounds of formula (II) in which: - Xi and X2 independently represent an oxygen atom; - Ri and R2 are independently monoalkyl ethers of (poly)alkylene glycol, in which a hydroxyl group has been removed; - n and z denote an integer from 1 to 20, with n+z > 2 and w is equal to 1; - Li is a C3-C15 cycloalkylene radical; - E independently represents a group selected from: -O-R3-O-; -S-R4-S-; -R5-N(R6)-R4-N(R6)-R5-; in which R3 and R4 are chosen independently from a C6-Ci4 arylene radical, a C3-C12 cycloalkylene radical, a linear or branched CrCi8 alkylene radical, possibly interrupted by one or more heteroatoms, and mixtures thereof; - when R5 is not a covalent bond, R5 is chosen from a C6-Ci4 arylene radical, a C3-C12 cycloalkylene radical, a linear or branched CrCi8 alkylene radical, possibly interrupted by one or more heteroatoms, and mixtures thereof; and - R6 is chosen from a C6-Ci4 arylene radical, a C3-C12 cycloalkylene radical, a linear or branched Ci-Ci8 alkylene radical, possibly interrupted by one or more heteroatoms, and mixtures thereof.

9. A method according to any one of claims 6 to 8, characterized in that the (poly)carbodihnide compound(s) is / are selected from the compounds of formula (II) in which: - Xi and X2 independently represent an oxygen atom; - Ri and R2 independently represent the compound of the following formula (VI): Ri3-[O-CH2-C(H)(Ri4)]q- (VI), in which Rn represents a CrC4 alkyl group or a phenyl group, preferably a Ci-C4 alkyl group, more preferably a methyl group, Ru represents a hydrogen atom or a CrC4 alkyl group, preferably a hydrogen atom, and q denotes an integer from 4 to 30; - n and z denote an integer from 1 to 20, with n+z ranging from 4 to 10 and w is equal to 1;- Li is a C3-C15 cycloalkylene radical such as cyclopentylene, cycloheptylene, cyclohexylene and 4,4-dicyclohexylene methane, and - E represents an -O-R3-O- group in which R3 is selected from a C6-Ci4 arylene radical, a C3-C12 cycloalkylene radical, a linear or branched CrCi8 alkylene radical, possibly interrupted by one or more heteroatom(s), and mixtures thereof.;

10. A method according to any one of claims 6 to 9, characterized in that the (poly)carbodihnide compound(s) is / are selected from compounds of formula (II) in which: - Xi and X2 independently represent an oxygen atom;

11. - Ri and R2 independently represent the compound with the following formula (VI): R13-[O-CH2-C(H)(R14)]q- (VI), in which R13 represents a C1-C4 alkyl group or a phenyl, preferably a Ci-C4 alkyl group, more preferably a methyl, R14 represents a hydrogen atom or a CrC4 alkyl group, preferably a hydrogen atom and q denotes an integer from 4 to 30; - n and z denote an integer ranging from 1 to 20, with n+z ranging from 4 to 10, and w is equal to 1; - Li is a C3-Ci5 cycloalkylene radical such as cyclopentylene, cycloheptylene, cyclohexylene, and 4,4-dicyclohexylene methane, preferably 4,4-dicyclohexylene methane; and - E represents a group- -O-R3-O- in which R3 represents a linear or Ci-Ci8 branched alkylene radical such as methylene, propylene, butylene, ethylene, possibly interrupted by one or more heteroatom(s). A process according to any one of claims 6 to 10, characterized in that the (poly)carbodiimide compound(s) is / are chosen from the compounds of the following formula (XII): (XII), in which Li is 4,4-dicyclohexylene methane, n and z denote an integer from 1 to 20, with n+z ranging from 4 to 10, E represents a group- -O-R3-O- in which R3 represents a linear or Ci-Ci8 branched alkylene radical such as methylene, propylene, butylene, ethylene, possibly interrupted by one or more heteroatom(s), and r and s denote an integer from 4 to 30.

12. A process according to any one of the preceding claims, characterized in that the total amount of the (poly)carbodiimide compound(s) ranges from 0.01 to 20% by weight, preferably from 0.1 to 15% by weight, more preferably from 0.2 to 10% by weight, even more preferably from 0.5 to 8% by weight, better from 1 to 6% by weight relative to the total weight of composition C.

13. A process according to any one of the preceding claims, characterized in that the polymer comprising at least one reactive group selected from carboxylic acids is an acrylic polymer.

14. A process according to the preceding claim, characterized in that the acrylic polymer(s) comprise one or more motifs derived from the following monomers: a) (meth)acrylic acid; and b) alkyl (meth)acrylate in C1 to C30, preferably in C1 to C20, more preferably in C1 to C10, and even more preferably in C1 to C4.

15. A process according to any one of the preceding claims, characterized in that the polymer(s) comprising at least one reactive group selected from carboxylic acids, preferably acrylic polymers, are present in a total quantity ranging from 0.1 to 35% by weight, more preferably from 0.5 to 30% by weight, better still from 1 to 20% by weight, and even more preferably from 3 to 15% by weight relative to the total weight of composition C.

16. A process according to any one of the preceding claims, characterized in that the total quantity of coloring agent(s) selected from pigments, direct colorants, and mixtures thereof ranges from 0.001 to 20% by weight, preferably from 0.005 to 15% by weight relative to the total weight of composition C.

17. A method according to any one of the preceding claims, characterized in that step b) consists of extemporaneously mixing At the time of use, at least two compositions A and B are used to obtain composition C, and composition C is applied to the hair, with: - composition A comprising at least one (poly)carbodiimide compound as defined in any one of claims 1 and 5 to 11; - composition B comprising at least one polymer comprising at least one reactive group selected from carboxylic acids as defined in any one of claims 1 and 13 to 14, composition A and / or composition B comprising at least one coloring agent selected from pigments, direct dyes, and mixtures thereof as defined in claim 1.

Citation Information

Patent Citations

  • Improved process for the production of carbodiimide modified organic isocyanates

    CA2509861A1

  • Composite particles, process for producing the same, and pigment, paint and resin composition using the same

    EP1184426A2

  • Use of an insoluble pigment obtained by oxidative polymerisation of indole derivatives for the temporary dyeing of keratinous fibres

    FR2679771A1

  • Metallic paint and method for coating therewith

    JP1993017710A

  • Resin composition

    JP1995258460A