Process for treating keratin fibres with compound derived from condensation of poly (thio) alcohol and acetoacetate and cross-linking agent

Abstract

The invention relates more particularly to the cosmetic field of keratin fibres, and in particular to the cosmetic field of caring, styling and / or dyeing keratin fibres and preferably the hair. The invention therefore relates to a method for using i) at least one compound of formula (I) derived from the condensation of a poly (thio) alcohol or polyamine and acetoacetate (ACAC) and ii) at least one cross-linking agent on keratin fibres in one or more steps. The invention also relates to a composition comprising components i) and ii), and also to a kit comprising i) and ii).

Description

[0001] The present invention more particularly relates to the field of beauty of keratin fibers, and in particular to the field of beauty for caring for, styling and / or dyeing keratin fibers and preferably hair. Thus, the present invention aims to provide a method for using i) at least one compound of formula (I) resulting from the condensation of a poly(thio)ol and acetoacetate (ACAC) and ii) at least one crosslinking agent on keratin fibers in one or more steps. The present invention also relates to a composition comprising components i) and ii), and also to a kit comprising i) and ii).

[0002] Cosmetic products conventionally require the use of one or more film-forming polymers in order to obtain a good deposit of these products on keratin fibers and in particular to meet the expectations detailed below.

[0003] Furthermore, in the hair care field, a new range of products called "Hair Makeup" has recently been developed. These products guarantee a temporary hair coloration that lasts after 1 to 3 shampoo washes. Thus, they are a particularly attractive alternative to permanent hair coloration for consumers, provided of course that the coloring effect is effectively guaranteed to last after contact with water and several shampoo washes. This requirement is particularly also met by using effective film formers. Thus, for example, for this purpose, FR 2 741 530 proposes, for the temporary dyeing of keratin fibers, to use a dispersion of film-forming polymer particles comprising at least one acidic functional group and at least one pigment dispersed in the continuous phase of said dispersion. The coloring obtained by this dyeing method is not always satisfactory in terms of persistence, especially with respect to shampoo washes. Specifically, generally, these polymers do not provide a deposit on keratin fibers that meets all of the above requirements (i.e., very good water resistance, especially with respect to shampoo washes of the hair, which makes it possible to adjust the gloss or invisible quality and provides a very satisfactory styling retention in the case of hair care applications).

[0004] US 2006 / 0079599 describes polymer-based tissue adhesives for medical use, which comprise certain polymers carrying ACAC groups, which are combined with polyamines in the form of hydrogels.

[0005] EP 3 250 177 A1 describes the use of acetoacetylated compounds in the field of keratin fibers. The keratin fibers treated with said acetoacetylated compounds do not always give satisfactory results, especially in terms of persistence with respect to water and shampoo washes.

[0006] There is also a need for cosmetic dye compositions intended for application to the hair, which cosmetic dye compositions have good water resistance and resistance to shampooing in order to ensure color persistence over time, especially in terms of intensity and / or chromaticity.

[0007] There is also a need for cosmetic compositions intended for hair application, especially non-coloring compositions, which have styling properties, especially hair hold, especially curl hold, and are resistant to water and shampooing.

[0008] The present invention precisely aims to meet all or some of these needs.

[0009] These problems are solved by using a method for treating said fibers by applying to keratin fibers, especially human keratin fibers such as hair, the following:

[0010] i) at least one compound of formula (I) and also its optical or geometric isomers, its salts and its solvates such as hydrates:

[0011] [Chemical formula 1]:

[0012]

[0013] In formula (I):

[0014] -R 1 represents a straight-chain or branched, saturated or unsaturated, conjugated or non-conjugated, acyclic or cyclic, aromatic or non-aromatic C2 to C 14 , especially C3 to C 12 polyvalent hydrocarbon radical group,

[0015] R 1 also:

[0016] a) optionally substituted by one or more hydroxyl OH or dialkylamino -N(R)2 groups, where R represents (C1-C4) alkyl such as methyl, carboxyl -C(O)-OH, vinyl, and / or

[0017] b) optionally interrupted by one or more heteroatoms or groups selected from: O, S, carbonyl -C(O)-, amine -N(R’), or combinations thereof such as ester -C(O)-O-, -O-C(O)-, amide -C(O)-N(R’)-, -N(R’)-C(O)-, carbamate -N(R’)-C(O)-O- or -O-C(O)-N(R’)-, urea -N(R’)-(CO)-N(R’)-, or carbonate -O-C(O)-O-, where R’ represents a hydrogen atom, a straight-chain or branched alkyl containing 1 to 4 carbon atoms, which is optionally substituted by at least one hydroxyl (OH), or optionally by -X-C(O)-C(R a)(R b )-C(O)-R 2 is substituted; preferably, R’ represents a hydrogen atom or a (C1-C4) alkyl group;

[0018] -R 2 represents a linear or branched, saturated or unsaturated C1 to C6 monovalent hydrocarbon radical group, preferably a (C1-C4) alkyl group such as methyl or tert-butyl, more preferably methyl;

[0019] -R a and R b may be the same or different and represent a hydrogen atom or a (C1-C4) alkyl group, preferably hydrogen;

[0020] -X is a heteroatom or group selected from: O, S, N(R’) or -S-CH2-C(O)-O-, -O-C(O)-CH2-S-, -O-C(O)-N(R’)-, -N(R’)-C(O)-O- or -N(R’)-C(O)-N(R’)-; preferably, X represents O;

[0021] -n indicates an integer ranging from 2 to 10, particularly from 3 to 8; and

[0022] ii) at least one crosslinking agent; and

[0023] iii) optionally at least one cosmetic active agent.

[0024] Thus, the inventors have surprisingly found that the application of components i), ii) and optionally iii) to keratin fibers provides tolerance to the effects on the keratin fibers treated with this combination, particularly with respect to washing with water and / or shampoo.

[0025] For the purposes of the present invention and unless otherwise indicated:

[0026] - The term “cosmetic active agent” means an organic or organosilicon compound or an inorganic compound that can be incorporated into a cosmetic composition to give an effect to keratin fibers, whether this effect is immediate or provided by repeated application. As examples of cosmetic active agents, mention may be made of colored or colorless, fluorescent or non-fluorescent compounds such as optical brighteners, or UVA and / or UVB screening agents, active agents intended to provide benefits to keratin fibers, antioxidant active agents, moisturizing active agents, active agents intended to counteract the effects of pollution, antimicrobial or bactericidal active agents, perfumes, active agents for caring for keratin fibers such as hair, and colorants such as direct dyes or pigments, preferably pigments. Preferably, the cosmetic active agent is selected from a) colorants selected from pigments, direct dyes and mixtures thereof, b) active agents for caring for keratin fibers, preferably hair, c) UV screening agents, and d) mixtures thereof.

[0027] - For the purposes of the present invention, the term "coloring persistent relative to shampooing" means that the obtained coloring persists after at least one shampooing, in particular after at least three shampooings, preferably after at least five shampooings.

[0028] - For the purposes of the present invention, the term "fatty substance" means an organic compound that is insoluble in water (solubility less than 5%, preferably less than 1% and even more preferably less than 0.1%) at normal temperature (25 °C) and at atmospheric pressure (760 mmHg); furthermore, the fatty substance is soluble in organic solvents under the same temperature and pressure conditions, for example soluble in halogenated solvents (such as chloroform or dichloromethane), lower alcohols (such as ethanol) or aromatic solvents (such as benzene or toluene).

[0029] - "Aryl" denotes a monocyclic or fused or non-fused polycyclic hydrocarbyl group containing 6 to 14 carbon atoms and having at least one aromatic ring; preferably, aryl is phenyl, biphenyl, naphthyl, indenyl, anthracenyl or tetrahydronaphthyl.

[0030] - "Heteroaryl" denotes a monocyclic or fused or non-fused 5- to 14-membered group containing 1 to 6 heteroatoms selected from nitrogen, oxygen, sulfur and selenium atoms and having at least one aromatic ring; preferably, heteroaryl is selected from acridinyl, benzimidazolyl, benzobisthiazolyl, benzopyrazolyl, benzopyridazinyl, benzquinolyl, benzothiazolyl, benzotriazolyl, benzoxazolyl, pyridyl, tetrazolyl, dihydrothiazolyl, imidazopyridyl, imidazolyl, indolyl, isoquinolyl, naphthimidazolyl, naphthoxazolyl, naphthopyrazolyl, oxadiazolyl, oxazolyl, oxazolopyridyl, phenazinyl, phenoxazolyl, pyrazinyl, pyrazolyl, pyrilyl, pyrazolyltriazolyl, pyridyl, pyridinimidazolyl, pyrrolyl, quinolinyl, tetrazolyl, thiadiazolyl, thiazolyl, thiazolopyridyl, thiazolylimidazolyl, thiopyrylyl, triazolyl and xanthylyl;

[0031] - The term "(hetero)aryl" means aryl or heteroaryl;

[0032] - The term "(hetero)cycloalkyl" means cycloalkyl or heterocycloalkyl;

[0033] - An "aryl" or "heteroaryl" group or the aryl or heteroaryl moiety of a group may be substituted by at least one substituent carried by a carbon atom, the at least one substituent being selected from:

[0034] · C1-C6 and preferably C1-C4 alkyl;

[0035] · Halogen atoms such as chlorine, fluorine or bromine;

[0036] · Hydroxyl;

[0037] · C1-C2 alkoxy; C2-C4 (poly)hydroxyalkoxy;

[0038] · Amino;

[0039] · Amino substituted by one or two identical or different C1-C6 and preferably C1-C4 alkyl groups;

[0040] · Amido (-N(R)-C(O)-R’), where the group R is a hydrogen atom;

[0041] · C1-C4 alkyl and the group R' is C1-C4 alkyl; Carbamoyl (R2N-C(O)-), where the group R may be the same or different and represents a hydrogen atom or C1-C4 alkyl;

[0042] · Alkylsulfonylamino (R’-S(O)2-N(R)-), where the group R represents a hydrogen atom or C1-C4 alkyl and the group R’ represents C1-C4 alkyl or phenyl;

[0043] · Sulfamoyl (R2N-S(O)2-), where the group R may be the same or different and represents a hydrogen atom or C1-C4 alkyl;

[0044] · Carboxylic acid group in acid form or salified (preferably salified with an alkali metal or a substituted or unsubstituted ammonium salt) form;

[0045] · Cyano (CN);

[0046] · Polyhalo (C1-C4) alkyl, preferably trifluoromethyl (CF3);

[0047] - The cyclic or heterocyclic moiety of the non-aromatic group may be substituted by at least one substituent carried by a carbon atom, and the at least one substituent is selected from the following groups:

[0048] · Hydroxyl,

[0049] · C1-C4 alkoxy, C2-C4 (poly)hydroxyalkoxy;

[0050] · Alkylcarbonylamino (RC(O)-NR’-), where the group R' is a hydrogen atom or C1-C4 alkyl and the group R is C1-C4 alkyl, amino substituted by one or two identical or different C1-C4 alkyl groups;

[0051] · Alkylcarbonyloxy (RC(O)-O-), where the group R is C1-C4 alkyl, amino substituted by one or two identical or different C1-C4 alkyl groups;

[0052] · an alkoxycarbonyl group (RO-C(O)-), where the group R is a C1-C4 alkyl group;

[0053] - The non-aromatic moiety of a cyclic or heterocyclic group, or an aryl or heteroaryl group, may also be substituted with one or more oxo groups;

[0054] - When the hydrocarbon chain contains one or more double bonds and / or one or more triple bonds, preferably one or more double bonds, the chain is unsaturated;

[0055] - "Cyclic group" or "cycloalkyl group" is a monocyclic or fused or unfused polycyclic, non-aromatic cyclic hydrocarbon group containing 5 to 14 carbon atoms, which may include one or more degrees of unsaturation; preferably, the cycloalkyl group is cyclohexyl;

[0056] - "Heterocyclic group" or "heterocycloalkyl group" is a monocyclic or fused or unfused polycyclic 3- to 9-membered non-aromatic cyclic group containing 1 to 4 heteroatoms selected from nitrogen, oxygen, sulfur and selenium atoms; preferably, the heterocycloalkyl group is selected from epoxides, piperazinyl, piperidinyl, morpholinyl and dithiolane;

[0057] - "Alkyl" is a straight-chain or branched-chain, especially C1-C6 and preferably C1-C4 saturated hydrocarbon group;

[0058] - "Alkoxy" is alkyl-oxy, where the alkyl is a straight-chain or branched-chain C1-C6 and preferably C1-C4 hydrocarbon group;

[0059] - "(Poly)(hydroxy)alkyl" denotes a C1-C6 and preferably C1-C4 alkyl group optionally substituted with one or more hydroxyl groups, preferably with 1 to 4 hydroxyl groups, more particularly 1 to 3;

[0060] - "Sugar" group is a monosaccharide or disaccharide group. Sugar groups that may be mentioned include: sucrose, glucose, galactose, ribose, fucose, maltose, fructose, mannose, arabinose, xylose and lactose;

[0061] - The term "monosaccharide" refers to a monosaccharidic glycoside sugar of the formula C x (H2O) x containing at least 5 carbon atoms, as well as its salts and solvates such as hydrates, where x is an integer greater than or equal to 5, preferably x is greater than or equal to 6, particularly x is 5 to 7 including the end values, preferably x = 6, which may have D or L configurations and have α or β anomers;

[0062] - The term "disaccharide" refers to a disaccharide glycoside sugar, which is a compound composed of two sugars bonded together via an O-glycosidic bond. The compound is composed of two monosaccharide units (also known as monoglycosides) as previously defined. The monosaccharide units contain at least 5 carbon atoms, preferably 6; in particular, the monoglycoside units are linked together via a 1,4 or 1,6 bond. As each glycoside unit can have an α (alpha) or β (beta) anomer in the L or D configuration, as well as its salts and solvates such as the hydrates of the monosaccharides; more particularly, they are polymers formed from two sugars (or monosaccharides) having the following general formula: -[C x (H2O) y )]2- or -[(CH2O) x 2-, where x is an integer greater than or equal to 5, preferably x is greater than or equal to 6, particularly x is 5 to 7 inclusive of the end values, preferably x = 6, and y is an integer representing x - 1;

[0063] - The term "polysaccharide" refers to a polysaccharide glycoside sugar, which is a polymer composed of at least 3 sugars bonded together via an O-glycosidic bond. The polymer is composed of monosaccharide units (also known as monoglycosides) as previously defined. The monosaccharide units contain at least 5 carbon atoms, preferably 6; in particular, the monoglycoside units are linked together via a 1,4 or 1,6 bond. As each glycoside unit can have an α (alpha) or β (beta) anomer in the L or D configuration, as well as its salts and solvates such as the hydrates of the monosaccharides; more particularly, they are polymers formed from a certain number of sugars (or monosaccharides) having the following general formula: -[C x (H2O) y )] w - or -[(CH2O) x w -, where x is an integer greater than or equal to 5, preferably x is greater than or equal to 6, particularly x is 5 to 7 inclusive of the end values, and preferably x = 6, and y is an integer representing x - 1, and w is an integer greater than or equal to 2, particularly 3 to 3000 inclusive of the end values, more particularly 5 to 2500, preferably 10 to 2300, particularly 15 to 1000 inclusive of the end values, more particularly 20 to 500, preferably 25 to 200;

[0064] ​- The term "organic or inorganic acid salt" more particularly means a) an addition salt with an organic or inorganic acid, especially a salt selected from those derived from: i) hydrochloric acid HCl, ii) hydrobromic acid HBr, iii) sulfuric acid H2SO4, iv) alkylsulfonic acids: Alk-S(O)2OH, such as methanesulfonic acid and ethanesulfonic acid; v) arylsulfonic acids: Ar-S(O)2OH, such as benzenesulfonic acid and toluenesulfonic acid; vi) alkoxysulfinic acids: Alk-O-S(O)OH, such as methoxysulfinic acid and ethoxysulfinic acid; vii) aryloxysulfinic acids, such as tolyloxysulfinic acid and phenoxysulfinic acid; viii) phosphoric acid H3PO4; ix) trifluoromethanesulfonic acid CF3SO3H and x) tetrafluoroboric acid HBF4; xi) organic carboxylic acids R°-C(O)-OH (I'z), in formula (I'z), R° represents (hetero)aryl such as phenyl, (hetero)aryl(C1-C4)alkyl such as benzyl, or (C1-C 10 )alkyl, said alkyl being optionally substituted preferably by one or more hydroxyl groups or amino groups or carboxyl groups, R° preferably denoting a (C1-C6)alkyl optionally substituted by 1, 2 or 3 hydroxyl groups or carboxyl groups; more preferably, the monocarboxylic acids of formula (I'z) are selected from acetic acid, glycolic acid, lactic acid, and mixtures thereof, and more particularly from acetic acid and lactic acid; and the polycarboxylic acids are selected from tartaric acid, succinic acid, fumaric acid, citric acid and mixtures thereof; and xii) amino acids comprising more carboxyl groups than amino groups, such as γ-carboxyglutamic acid, aspartic acid or glutamic acid, especially γ-carboxyglutamic acid; or b) an addition salt with an organic or inorganic base such as an alkali metal or alkaline earth metal hydroxide, an alkali metal or alkaline earth metal carbonate, an alkali metal or alkaline earth metal bicarbonate, an addition salt with a basic amino acid such as arginine or lysine, an addition salt with an optionally hydroxylated amine;

[0065] - "Anionic counterion" is an anion or anionic group associated with a cationic charge; more particularly, the anionic counterion is selected from: i) halide ions, such as chloride ion or bromide ion; ii) nitrate; iii) sulfonate, including C1-C6 alkylsulfonate: Alk-S(O)2O - , such as methanesulfonate or mesylate and ethanesulfonate; iv) arylsulfonate: Ar-S(O)2O - , such as benzenesulfonate and toluenesulfonate (toluenesulfonate or tosylate); v) citrate; vi) succinate; vii) tartrate; viii) lactate; ix) alkylsulfate: Alk-O-S(O)O - , such as methylsulfate and ethylsulfate; x) arylsulfate: Ar-O-S(O)O - , such as benzenesulfate and toluenesulfate; xi) alkoxysulfate: Alk-O-S(O)2O -, such as methoxysulfate and ethoxysulfate; xii) aryloxysulfate: Ar-O-S(O)2O - ; xiii) phosphate; xiv) acetate; xv) trifluoromethanesulfonate; and xvi) borate such as tetrafluoroborate;

[0066] - "Solvate" means a hydrate and also a combination with a straight-chain or branched C1-C4 alcohol such as ethanol, isopropanol or n-propanol;

[0067] - The term "chromophore" means a group derived from a colorless or colored compound capable of absorbing in the range of UV and / or visible light radiation at a wavelength λ from 250 to 800 nm. Preferably, the chromophore is colored, i.e., it absorbs wavelengths in the visible light range (i.e., preferably from 400 to 800 nm). Preferably, the chromophore appears colored to the eye, particularly from 400 to 700 nm (Ullmann's Encyclopedia, 2005, Wiley-VcH, Verlag "Dyes, General Survey", §2.1 Basic Principle of Color); abs - The term "UV-A screening agent" means a chromophore derived from a compound that screens (or absorbs) UV-A ultraviolet rays at a wavelength from 320 to 400 nm. A distinction can be made between short UV-A screening agents (which absorb rays at a wavelength from 320 to 340 nm) and long UV-A screening agents (which absorb rays at a wavelength from 340 to 400 nm).

[0068] - The term "UV-B screening agent" means a chromophore derived from a compound that screens (or absorbs) UV-B ultraviolet rays at a wavelength from 280 to 320 nm.

[0069] - The term "anhydrous" means an amount of water that is less than 5% by weight, preferably less than 3% by weight, still better less than 1% by weight, relative to the total weight of the composition C1, C2, C3 or C4 under discussion; even more preferably, the composition is free of water;

[0070] - The terms "colorant" and "dye" are equivalent.

[0071] - Unless otherwise indicated, the limiting values of the bounds of a defined range of values are included within that range of values.

[0072] - Unless otherwise indicated, the amounts indicated are expressed as mass percentages.

[0073]

[0074] ​Method for treating keratin fibers

[0075] The first subject of the present invention is a method for using the following on keratin fibers, in particular hair, in one or more steps:

[0076] i) at least one compound of formula (I) as defined previously and hereinafter;

[0077] iii) at least one crosslinking agent as defined hereinafter; and

[0078] iii) optionally at least one cosmetic active agent as defined previously and hereinafter.

[0079] According to a specific embodiment of the invention, the method of the invention comprises the step of simultaneously applying components i), ii) and optionally iii).

[0080] According to another specific embodiment of the invention, the method comprises at least two steps, in which components i), ii) and optionally iii) (the latter component may be present together with component i) and / or with component ii)) are applied to the keratin fibers in separate consecutive steps.

[0081] According to a specific embodiment, component i) is applied to the keratin fibers, and then component ii) is applied to the keratin fibers, it being understood that components iii) (when they are present) may be applied together with i) and / or ii).

[0082] According to another specific embodiment, component ii) is applied to the keratin fibers, and then component i) is applied to the keratin fibers, it being understood that components iii) (when they are present) may be applied together with i) and / or ii).

[0083] According to a specific embodiment of the invention, the method for treating keratin fibers is a method for caring for, styling and / or coloring keratin fibers, preferably hair.

[0084] According to another embodiment of the invention, the method for treating keratin fibers is a hair coloring method.

[0085] According to one aspect of the invention, the method of the invention for treating keratin fibers with components i), ii) and optionally iii) is a hair care treatment.

[0086] According to another aspect of the invention, the method of the invention for treating keratin fibers with components i), ii) and optionally iii) is a method for styling and / or coloring keratin fibers.

[0087] According to one embodiment of the invention, the method for treating keratin fibers uses:

[0088] - A composition designated as "C1", which comprises i) at least one compound of formula (I) or (Ia) as defined previously and hereinafter, and optionally iii) at least one cosmetic active agent as defined previously and hereinafter; preferably, composition C1 does not contain any crosslinking agent;

[0089] - A composition designated as "C2", which comprises i) at least one compound of formula (I) or (Ia) as defined previously and hereinafter, and ii) at least one crosslinking agent as defined hereinafter, and optionally iii) at least one cosmetic active agent as defined previously and hereinafter;

[0090] - A composition designated as "C3", which comprises i) at least one compound of formula (I) or (Ia) as defined previously and hereinafter, ii) at least one crosslinking agent as defined hereinafter, and iii) at least one cosmetic active agent as defined previously; and / or

[0091] - Composition "C4", which comprises ii) at least one crosslinking agent as defined hereinafter, and optionally iii) at least one cosmetic active agent as defined previously and hereinafter; preferably, composition C4 does not contain any compound of formula (I) or (Ia);

[0092] - Composition "C5", which comprises iii) at least one cosmetic active agent as defined previously and hereinafter; preferably, composition C5 does not contain i) any compound of formula (I), or ii) any crosslinking agent as defined hereinafter;

[0093] It should be understood that:

[0094] · The method uses i) at least one compound of formula (I) or (Ia) as defined previously and hereinafter and ii) at least one crosslinking agent as defined hereinafter, either together or separately; and

[0095] · Compositions C1, C2, C3, C4 and C5 can be anhydrous, aqueous such as water - alcohol, and / or contain one or more fatty substances iv), in particular one or more volatile oils preferably as defined hereinafter.

[0096] According to one aspect of the invention, a method for treating keratin fibers, in particular for caring for, styling and / or dyeing keratin fibers, especially hair, uses a composition called "C1", which composition comprises i) as defined previously and hereinafter, and optionally iii) at least one cosmetic active agent as defined hereinafter, which cosmetic active agent is especially selected from a) colorants such as pigments, direct dyes, and mixtures thereof, b) active agents for caring for keratin fibers, c) UV screening agents, and d) mixtures thereof, and especially at least one colorant, more particularly at least one pigment.

[0097] According to another aspect, a method of the invention for treating keratin fibers, in particular for caring for, styling and / or dyeing keratin fibers, uses a composition called "C2", which composition comprises i) at least one compound of formula (I) as defined previously and hereinafter, and ii) at least one crosslinking agent as defined hereinafter, and optionally iii) at least one cosmetic active agent as defined previously.

[0098] According to another aspect, a method of the invention for treating keratin fibers, in particular for caring for, styling and / or dyeing keratin fibers, uses a composition called "C3", which composition comprises i) at least one compound of formula (I) as defined previously and hereinafter, ii) at least one crosslinking agent as defined hereinafter, and iii) at least one cosmetic active agent as defined previously.

[0099] According to another aspect, a method of the invention for treating keratin fibers, in particular for caring for, styling and / or dyeing keratin fibers, uses a composition called "C1" and a composition called "C4", said composition "C1" comprising i) at least one compound of formula (I) as defined previously and hereinafter and optionally iii) at least one cosmetic active agent as defined previously, and said composition "C4" comprising ii) at least one crosslinking agent as defined hereinafter, and optionally iii) at least one cosmetic active agent as defined previously.

[0100] According to another variant of the method of the invention, during a first step, components i) and optionally iii) are applied together (i.e., simultaneously) to the keratin fibers, and then, during a subsequent step, components ii) and optionally iii) are applied to said keratin fibers. According to a specific embodiment of the method, in the first step, the composition "C1" is applied to the keratin fibers, and then a composition "C4" comprising ii) at least one crosslinking agent and optionally iii) at least one cosmetic active agent as defined previously is applied to said fibers.

[0101] According to yet another variant of the method of the invention, component ii) and optionally iii) are applied to the keratin fibers, and then component i) and optionally at least one cosmetic active agent as previously defined for iii) are applied to the fibers. In particular, composition C4 is applied to the keratin fibers, and then composition C1 is applied.

[0102] Compositions C1, C2, C3, C4 and / or C5 of the method of the invention comprising at least one fatty substance, in particular at least one oil and water, can be in the form of a direct or inverse emulsion.

[0103] Thus, compositions C1, C2, C3, C4 and / or C5 of the method of the invention can be applied directly as such to the target keratin fibers, or can even be formed directly on the surface of these keratin fibers.

[0104] According to yet another variant of the method of the invention, component ii), in particular a metal alkoxide and more particularly a titanium alkoxide such as titanium butoxide and optionally iii) are applied to the keratin fibers, and then component i) and optionally at least one cosmetic active agent as previously defined for iii) are applied to the fibers. In particular, composition C4 is applied to the keratin fibers, and then composition C1 is applied.

[0105] According to another variant of the method of the invention, components i), ii) and optionally iii) are applied together during a first step, and then a component ii) which is the same as or different from the component ii) used in the first step is applied again to the keratin fibers during a subsequent step. According to a specific embodiment of the method, in the first step, composition "C2" or composition "C3" is applied to the keratin fibers, and then composition "C4" comprising ii) at least one crosslinking agent and optionally iii) at least one cosmetic active agent as previously defined is applied to the fibers.

[0106] According to the invention, three application methods are thus distinguished, called "single gesture application mode", "two gesture application mode" and "three gesture application mode".

[0107] According to one embodiment of the method of the invention, it is carried out in a single gesture by applying composition C2 or C3 as previously defined to the keratin fibers.

[0108] The term "single gesture application mode" means the direct application to the target keratin fibers of a single composition according to the invention, i.e. composition C2 or C3.

[0109] After applying composition C2 or C3, a deposit is advantageously obtained which is persistent with respect to washing with water and / or shampoo, and / or has good retention of the shape of the keratin fibers, in particular of the curls, and / or makes styling easy and / or gives a pleasant feel to the keratin fibers, and may give body to said fibers. The deposit obtained is also resistant to water and / or to shampoo washing.

[0110] According to another embodiment of the method according to the invention, it is carried out in two gestures.

[0111] The term "two-gesture application mode" means the successive application of two different compositions, for example C1 and C4, or C2 and C4, or C3 and C4, to the target keratin fibers. Preferably, C1 and then C4, C2 and then C4, or C3 and then C4. The two-gesture application mode may in particular comprise the successive application of composition C2 or C3 and composition C4, preferably C2 or C3 and then C4, to the keratin fibers.

[0112] In the two-gesture application mode, the composition applied first to the keratin fibers (for example C1) is conventionally called the "base coat", and the composition applied on top of it (for example C4) is generally called the "top coat".

[0113] According to another embodiment, the method of the invention is carried out in three gestures.

[0114] The term "three-gesture application mode" means the successive application of three different compositions C1 to C5. According to this application mode, for example, the successive application of α) composition C1, then β) composition C4, then γ) composition C5, preferably C1 then C4 then C5, or C1 then C5 then C4, is carried out on the keratin fibers. According to another option, the successive application of α) a composition such as C4, and β) composition C1 or C2, and even γ) composition C5, is carried out on the keratin fibers; preferably, composition C4 is applied before composition C1.

[0115] In the two-gesture or three-gesture application mode, the composition applied first (for example C1) is conventionally called the "base coat", and the composition applied on top of it is generally called the "top coat".

[0116] After applying the various compositions C1 to C5, a deposit is advantageously obtained which is persistent on the keratin fibers and / or has good retention of the shape of the keratin fibers, in particular of the curls, and / or makes styling easy and / or has a pleasant feel. The deposit obtained on said fibers is also in particular resistant to water and / or to shampoo washing.

[0117] According to a specific embodiment, the composition is applied to dry keratin fibers after combing and natural drying or drying with a hair dryer, preferably a hair dryer.

[0118] According to a specific embodiment, the keratin fibers are dried after applying compositions C1 to C5, in particular after applying each different composition. The drying step can be carried out with a drying device such as a hood, a hair dryer or a Climazon. When the drying step is carried out with a hood or a hair dryer, the drying temperature is higher than 40 °C.

[0119] After the drying step, the step of shaping the keratin fibers can be carried out with a straightening iron, a wavy or curly iron or a steam iron, preferably a straightening iron or a steam iron. Preferably, the shaping step is carried out at a temperature higher than 100 °C. The iron can be applied to the keratin fibers by separate back-and-forth movements for several seconds in succession, or by gradually moving or gliding along the hair. Preferably, the iron is applied in one or more passes with a continuous movement from the roots to the ends of the hair.

[0120] According to one aspect, the present invention relates to a method for dyeing keratin fibers, in particular hair, which method comprises the step of applying to said hair a composition C2 or C3 which contains in particular at least one dye as previously defined and more particularly at least one pigment.

[0121] According to another aspect of the present invention, the present invention relates to a method for dyeing keratin fibers, in particular human keratin fibers, in particular hair, which method comprises at least the sequential application of:

[0122] - composition C1 as previously defined; and then

[0123] - composition C4 as previously defined;

[0124] It should be understood that composition C1 and / or C4 contains at least one dye as defined below, preferably at least one pigment. Preferably, composition C1 contains at least one pigment.

[0125] According to another aspect of the present invention, the present invention relates to a method for dyeing keratin fibers, in particular human keratin fibers, in particular hair, which method comprises at least the sequential application of:

[0126] - composition C1 as previously defined; and then

[0127] - composition C4 as previously defined; and

[0128] - composition C5 as previously defined;

[0129] It should be understood that composition C1 and / or C4 and / or C5 contains at least one colorant as defined below, preferably at least one pigment. Preferably, composition C5 contains at least one pigment.

[0130] According to another aspect of the present invention, the present invention relates to a method for dyeing keratin fibers, especially human keratin fibers, in particular hair, the method comprising at least sequentially applying:

[0131] - composition C2 as defined previously; and then

[0132] - composition C4 as defined previously;

[0133] It should be understood that composition C2 and / or C4 contains at least one colorant as defined below, preferably at least one pigment. Preferably, composition C4 contains at least one pigment.

[0134] According to yet another aspect of the present invention, the present invention relates to a method for dyeing keratin fibers, especially human keratin fibers, in particular hair, the method comprising at least sequentially applying:

[0135] - composition C2 as defined previously;

[0136] - composition C4 as defined previously; and

[0137] - composition C5 as defined previously;

[0138] It should be understood that composition C2 and / or C4 and / or C5 contains at least one colorant as defined below, preferably at least one pigment. Preferably, composition C5 contains at least one pigment.

[0139] According to another aspect of the present invention, the present invention relates to a method for making up keratin materials, especially keratin fibers, in particular human keratin fibers, especially hair, the method comprising at least sequentially applying:

[0140] - composition C1, C2 or C3 as defined previously; and

[0141] - composition C4 as defined previously;

[0142] - It should be understood that at least one of these compositions contains at least one cosmetic active ingredient iii), which is selected from colorants, preferably selected from pigments.

[0143] i) Compound of formula (I)

[0144] The first component of the method of the present invention is the compound of formula (I) as defined previously.

[0145] According to a specific embodiment of the present invention, component (i) is selected from those of formula (Ia) and also their optical or geometric isomers, their salts and their solvates such as hydrates:

[0146] [Chemical formula 2]:

[0147]

[0148] In formula (Ia):

[0149] -R 1 is as previously defined and in particular represents a linear or branched, saturated or unsaturated, conjugated or non-conjugated, acyclic or cyclic, aromatic or non-aromatic C2 to C 14 , preferably C3 to C 12 and preferably C4 to C 10 polyvalent hydrocarbon radical, R 1 also:

[0150] a) optionally substituted by one or more hydroxyl groups OH, and / or

[0151] b) optionally interrupted by one or more heteroatoms or groups selected from O, S, -N(R'), preferably interrupted by one or more oxygen atoms, where R' is as defined in formula (I);

[0152] -R 2 is as previously defined, preferably R 2 represents a linear or branched (C1-C6) alkyl group, preferably a (C1-C4) alkyl group, especially methyl or tert-butyl, such as methyl; and

[0153] -n is as previously defined; preferably, n indicates an integer in the range from 2 to 8.

[0154] According to one embodiment, the compounds of formula (I) and (Ia) are such that: R 1 represents a linear or branched, unsaturated monocyclic or bicyclic, preferably monocyclic C6 to C8 polyvalent hydrocarbon radical and an aromatic radical such as phenyl.

[0155] According to another embodiment, the compounds of formula (I) and (Ia) are such that: R 1 represents a saturated monocyclic or bicyclic C5 to C 12 polyvalent hydrocarbon radical, which is optionally interrupted by one or more heteroatoms or groups selected from O, S and -N(R')-, where R' represents a hydrogen atom or an alkyl group containing 1 to 4 carbon atoms, preferably interrupted by one or more oxygen atoms. Preferably, R 1represents a monosaccharide or polysaccharide unit, especially a disaccharide, on which n hydroxyl groups have been replaced by n groups -O-C(O)-CH2-C(O)-R 2 wherein R 2 is as previously defined and n is as previously defined.

[0156] Suitable monosaccharides according to the invention include but are not limited to ribose, glucose, mannose, galactose, fructose and sorbose.

[0157] According to one embodiment, the disaccharide is selected from cellobiose, maltose, lactose, raffinose, sucrose, trehalose, melibiulose, melibiose, mannotriose, kojibiose, aspergillose, isomaltose, rutinose, rutinulose and xylobiose.

[0158] According to another preferred embodiment of the invention, the compounds of formula (I) and (Ia) are such that: R 1 represents a straight-chain or branched-chain, saturated or unsaturated, preferably saturated, acyclic C2-C 12 , preferably C3-C 10 polyvalent hydrocarbon radical group.

[0159] According to a specific embodiment of the invention, the compounds of formula (I) and (Ia) are such that: n denotes an integer from 2 to 8; more particularly, n denotes an integer from 3 to 6, more particularly from 3 to 5. According to one embodiment, the compounds of formula (I) and (Ia) are such that: n is 2. According to another embodiment, the compounds of formula (I) and (Ia) are such that: n is 3. According to another embodiment, the compounds of formula (I) and (Ia) are such that: n is 4. According to another embodiment, the compounds of formula (I) and (Ia) are such that: n is 5. According to another embodiment, the compounds of formula (I) and (Ia) are such that: n is 6.

[0160] In a variant of the invention, the compound of formula (I) or (Ia) as previously defined is a mixture of compounds of different chemical structures.

[0161] More particularly, the compounds of formula (I) and (Ia) are selected from the following compounds, as well as their optical isomers, their salts and their solvates such as hydrates:

[0162]

[0163]

[0164]

[0165]

[0166]

[0167]

[0168]

[0169]

[0170]

[0171]

[0172] Wherein R1 may be the same or different and represents a hydrogen atom or a -C(O)-CH2-C(O)-CH3 group, it is understood that at least two groups R1 represent -C(O)-CH2-C(O)-CH3, and preferably at least three groups R1 represent -C(O)-CH2-C(O)-CH3.

[0173] More preferably, the compounds of formula (I) and (Ia) are selected from compounds (16), (18), (21), (35), (36), (37), (38), (39), (40) and (46), and even better (16), (21), (35), (38), (39) and (46).

[0174] Even more preferably, the compounds of formula (I) and (Ia) are selected from compounds (16), (18), (21), (35), (36), (37), (38), (39) and (40), and even better (16), (21), (35), (38) and (39).

[0175] Advantageously, the compounds of formula (I) and (Ia) are selected from compounds (18), (21), (36), (37), (38), (39) and (40), and even better (21), (38) and (39).

[0176] The compounds of formula (I) or (Ia) as defined previously are preferably present in a mass ratio of 0.2% to 100%, particularly 0.5% to 50%, more particularly 2% to 35% relative to the total weight of the composition C1, C2 or C3 containing them. In particular, the crosslinking agent and the compounds of formula (I) or (Ia) are preferably present in a mass ratio of 7% to 35% relative to the total weight of the composition containing them.

[0177] The compounds of formula (I) can be prepared from n equivalents of a dicarbonyl reagent and a nucleophile R containing n equivalents of a nucleophilic functional group -XH according to the following scheme 1 (XH) nobtained by (poly)condensation:

[0178] [Chemical formula 3]:

[0179]

[0180] In this scheme:

[0181] -R 1 、R 2 、R a 、R b and n are as defined for the compounds of formula (I); and

[0182] -R 3 represents a hydrogen atom, a (C1-C4) alkyl group such as methyl, ethyl, isobutyl, tert-butyl, or an electrofugal group such as CHal3, or Hal3C-SO2- such as trifluoromethanesulfonate, where Hal may be the same or different and represents a halogen atom;

[0183] -X’ represents an oxygen or sulfur atom, preferably O.

[0184] These (poly)condensation methods are known to those skilled in the art: for example, “From rigid and flexible foams to elastomers via Michael addition chemistry”, Polymer, 106, 128-139, (2016), “Dynamic Curing Agents for Amine-Hardened Epoxy Vitrimers with Short (Re)processing Times”, Macromolecules, 53(7), 2485-2495 (2020), “Super photo-base initiated organic-inorganic hybrid coatings by plural-cure mechanisms”, Progress in Organic Coatings, 127, 222-230 (2019) or patent application PL159100: Method for manufacturing acetylacetate esters can be mentioned.

[0185] According to a specific embodiment of the present invention, R 1 (XH) n is selected from acyclic polyols R 1 (OH) n , and in particular from glycerol, trimethylolpropane, ethylene glycol, diethylene glycol, triethylene glycol, tetraethylene glycol, propylene glycol, dipropylene glycol, butylene glycol, trimethylolethane, pentamethylene glycol, trimethylpentanediol, pentanediol, isosorbide, pentaerythritol, dipentaerythritol, hexamethylene glycol, hexanediol, neopentyl glycol, 1,2 - propanediol; 1,3 - propanediol; 1,2 - butanediol, 1,3 - butanediol, 2,3 - butanediol, 1,4 - butanediol; 2,4 - butanediol, 3,4 - butanediol; 1,4 - pentanediol; 1,5 - pentanediol, 2,2,4 - trimethyl - 1,3 - pentanediol, 1,6 - hexanediol, 1,2 - octanediol, 1,8 - octanediol, 1,10 - decanediol, 2 - methyl - 1,3 - propanediol, hexanediol and isopentyl glycol.

[0186] In one variant, R 1 (XH) n is selected from cyclic polyols R 1 (OH) n , and in particular from monosaccharides and disaccharides as previously defined, either alone or as a mixture.

[0187] Preferably, R 1 (XH) n is selected from polyols R 1 (OH) n , either alone or as a mixture, and in particular from trimethylolethane, glycerol, trimethylolpropane, pentaerythritol, glycerol, glucose, sucrose and sorbitol.

[0188] According to another variant, R 1 (XH) n is selected from diamines R 1 (NH2)2, especially hydroxyalkylated aliphatic diamines such as o,o’ - bis(diethanolaminomethyl) - p - nonylphenol, N,N,N,N’ - tetra(2 - hydroxypropyl)ethylenediamine (Quadrol L, available from BASF) and N,N,N,N - tetra(2 - hydroxyethyl)ethylenediamine, and mixtures thereof.

[0189] According to another advantageous variant, the compound of formula (I) or (Ia) is obtained by (poly)condensation of n equivalents of a propylenedioxycarbonyl reagent with a polyamine nucleophilic reagent R 1 (NH) n containing n equivalents of - NH2 nucleophilic functional groups according to the following scheme:

[0190] [Chemical Formula 4]:

[0191]

[0192] In this scheme:

[0193] -R 1 、R 2 、R a and n are as defined for the compounds of formula (I);

[0194] -R 1 -NH2 is especially selected from ethylenediamine, 1,3-diaminopropane, cadaverine, hexamethylenediamine, 1,2-diaminopropane, 1,2-diaminocyclohexane, and phenylenediamine; and

[0195] -R b’ and R c ’ can be the same or different and represent a hydrogen atom or a (C1-C4) alkyl group.

[0196] This type of synthesis method according to Scheme 2 is known to those skilled in the art: for example, “Acetoacetylation with 2,2,6-trimethyl-4H-1,3-dioxin-4-one: a convenient alternative to diketene”, Journal of Organic Chemistry, 50(14), 2431-5, (1985) or “Synthesis of new Biginelli polycondensates: renewable materials with tunable high glass transition temperatures”, Polymer International, 70(5), 506-513(2021) can be mentioned.

[0197] According to another advantageous variant, the compound of formula (I) or (Ia) is obtained by (poly)condensation of n equivalents of diketene reagent with a nucleophile R containing n equivalents of nucleophilic functional group -XH 1 (X) n as follows:

[0198] [Chemical Formula 5]

[0199]

[0200] In this process:

[0201] R 1 and n are as defined for the compounds of formula (I);

[0202] X' represents an oxygen or sulfur atom, or N(R'), where R' = H.

[0203] This type of method is known to those skilled in the art. For example, "Acetoacetamides, 2-hydroximinoacetoacetamides, and 2,3-bis(hydroximino)butyramides", Journal fur Praktische Chemie (Leipzig), 323(2), 337-44, (1981) or Angewandte Makromolekulare Chemie, 9, 96-105, (1969) may be mentioned.

[0204] ii) Crosslinking agent

[0205] The process of the invention uses ii) one or more crosslinking agents.

[0206] For the purposes of the present invention, the term "crosslinking agent", also referred to as "R", denotes a compound which is capable of establishing with at least one ACAC functional group of a compound of formula (I) or (Ia) the following:

[0207] - at least one covalent bond,

[0208] - at least one donor-acceptor (coordinate) bond, and / or

[0209] - at least one coordination bond

[0210] and thus crosslinks the compound of formula (I) or (Ia).

[0211] Preferably, the term "crosslinking agent" denotes a compound which is capable of establishing at least one covalent bond with the ACAC functional group of a compound of formula (I) or (Ia).

[0212] For the purposes of the present invention, it should be understood that the terms "crosslinking agent" and "crosslinker" are equivalent.

[0213] Compositions C2, C3 and C4 contain at least one crosslinking agent. The compositions of the present invention may comprise an oily phase, an aqueous phase or may be in the form of a direct or inverse emulsion. Composition C4 may be an aqueous composition.

[0214] According to one aspect, the method of the present invention uses a composition designated "C3", in particular a cosmetic composition for keratin fibres, especially for caring for, styling and / or colouring keratin fibres, which composition comprises i) at least one compound of formula (I) as previously defined, ii) at least one crosslinking agent and iii) at least one cosmetic active agent as previously defined and in particular at least one colourant, more particularly at least one pigment.

[0215] Compositions C2, C3 and C4 can be obtained by mixing an aqueous dispersion and / or a composition comprising at least one crosslinking agent R and at least one cosmetic active agent selected from a) to d) as previously defined.

[0216] The crosslinking agent as previously defined is preferably present in a mass ratio of from 0.2% to 60%, particularly from 0.5% to 40% and more particularly from 5% to 40% relative to the total weight of the composition containing it. In particular, the crosslinking agent and the compound of formula (I) or (Ia) are preferably present in a mass ratio of from 7% to 35% relative to the total weight of the composition containing them.

[0217] More precisely, the crosslinking agent R suitable for the present invention may be selected from compounds carrying amine, thiol, acrylate and / or carbonyl functional groups (such as ketone or aldehyde functional groups). The crosslinking agent R may also denote metal alkoxides.

[0218] Thus, according to a particular embodiment, the crosslinking agent R is selected from (poly)amines, (poly)thiols, (poly)carbonyls, (poly)acrylates and / or metal alkoxide compounds, and mixtures thereof, and is preferably selected from (poly)amines, (poly)thiols and (poly)acrylate compounds, metal alkoxides, and mixtures thereof.

[0219] The terms "(poly)amines, (poly)thiols, (poly)carbonyls and (poly)acrylate compounds" are intended to denote compounds containing respectively at least one primary or secondary amine, thiol, carbonyl (such as ketone or aldehyde functional group) or acrylate functional group.

[0220] A) (Poly)amine compound

[0221] According to a preferred embodiment, the crosslinking agent R is selected from (poly)amine compounds.

[0222] (Poly)amine compounds can be particularly selected from polyamine compounds carrying several primary and / or secondary amine groups or from aminoalkoxysilanes, and more particularly from aminoalkoxysilane compounds, diamine compounds, triamine compounds, and mixtures thereof.

[0223] (Poly)amine compounds can be compounds containing from 2 to 20 carbon atoms, especially non-polymeric compounds; they can be acyclic or cyclic, straight-chain or branched-chain, saturated or unsaturated, conjugated or non-conjugated, aromatic or non-aromatic, optionally interrupted by one or more heteroatoms selected from O, S, Si(R’)2, N(R”), preferably O, Si(R’)2, or combinations thereof such as -Si(R’)2-O- or -O-Si(R’)2-, where R' can be the same or different and represents a (C1-C4)alkyl such as methyl, and R” represents a hydrogen atom or a (C1-C4)alkyl, preferably hydrogen.

[0224] The term "non-polymeric compound" means a compound that is not directly obtained via a monomer polymerization reaction.

[0225] Particularly mentionable (poly)amine compounds include N-methyl-1,3-diaminopropane, N-propyl-1,3-diaminopropane, N-isopropyl-1,3-diaminopropane, N-cyclohexyl-1,3-diaminopropane, 2-(3-aminopropylamino)ethanol, 3-(2-aminoethyl)aminopropylamine, bis(3-aminopropyl)amine, methylbis(3-aminopropyl)amine, N-(3-aminopropyl)-1,4-diaminobutane, N,N-dimethyldipropylenetriamine, 1,2-bis(3-aminopropylamino)ethane, N,N’-bis(3-aminopropyl)-1,3-propanediamine, ethylenediamine, 1,3-propanediamine, 1,4-butanediamine, lysine, cystamine, xylenediamine, tris(2-aminoethyl)amine, 1,3-bis(aminomethyl)cyclohexane, 1,4-bis(aminomethyl)cyclohexane, diaminopropanol, 4,7,10-trioxa-1,13-tridecanediamine, spermidine, and C36-alkylenediamines (Priamine TM 1071, 1073, 1074, and 1075 sold by Croda respectively).

[0226] According to a specific embodiment of the present invention, the (poly)amine compounds are monoamine compounds, i.e., they contain only one primary and / or secondary amine group, preferably a primary amine group (NH2).

[0227] (Poly)amine compounds can be selected from aminoalkoxysilanes, especially the aminoalkoxysilane of the formula R’1Si(OR’2) z (R’3) x wherein:

[0228] - R'1 is a straight-chain or branched-chain, saturated or unsaturated, cyclic or acyclic C1-C6 hydrocarbon group chain, which is substituted by a group selected from a primary amine group NH2 or a secondary amine group -N(H)R, where R represents a C1-C4 alkyl group, an aryl group or a benzyl group substituted by an amino group or a C1-C4 aminoalkyl group; R'1 may have a heteroatom (O, S, NH) or a carbonyl group (CO) inserted in its chain, and R'1 is directly connected to the silicon atom via a carbon atom.

[0229] - R’2 and R’3 may be the same or different and represent straight-chain or branched-chain (C1-C6) alkyl groups.

[0230] - z indicates an integer ranging from 1 to 3, and

[0231] - x indicates an integer ranging from 0 to 2.

[0232] where z + x = 3.

[0233] In particular, R'1 is an acyclic chain. Preferably, R'1 is a straight-chain or branched-chain, saturated or unsaturated C1-C6 hydrocarbon group chain substituted by an amine -NH2 or -N(H)R group, where R represents a C1-C6 alkyl group, a C3-C6 cycloalkyl group or a C6 aromatic group. More preferably, R'1 is a saturated straight-chain C1-C6 hydrocarbon group chain substituted by an amine group NH2. Even more preferably, R'1 is a saturated straight-chain C2-C4 hydrocarbon group chain substituted by an amine group NH2.

[0234] In particular, R'2 represents an alkyl group containing 1 to 4 carbon atoms; preferably, R’2 represents a straight-chain alkyl group containing 1 to 4 carbon atoms, and more preferably R’2 represents an ethyl group.

[0235] In particular, R’3 represents an alkyl group containing 1 to 4 carbon atoms; preferably, R’3 represents a straight-chain alkyl group containing 1 to 4 carbon atoms, and more preferably R’3 represents a methyl group or an ethyl group. Preferably, z is equal to 3.

[0236] In particular, the (poly)amine compound is selected from aminoalkoxysilanes containing only one primary amine and / or secondary amine group, preferably a primary (NH2) amine group, such as 3-aminopropyltriethoxysilane (APTES), 3-aminoethyltriethoxysilane (AETES), 3-aminopropylmethyldiethoxysilane, N-(2-aminoethyl)-3-aminopropyltriethoxysilane, 3-(m-aminophenoxy)propyltrimethoxysilane, p-aminophenyltrimethoxysilane and N-(2-aminoethylaminomethyl)phenethyltrimethoxysilane.

[0237] Preferably, the (poly)amine compound is selected from 3-aminopropyltriethoxysilane (APTES), 3-aminoethyltriethoxysilane (AETES), 3-aminopropylmethyldiethoxysilane, and N-(2-aminoethyl)-3-aminopropyltriethoxysilane, and more preferably 3-aminopropyltriethoxysilane (APTES) or its oligomer.

[0238] (Poly)amine compounds may also be selected from amino polymers, which particularly have a weight-average molecular weight in the range of 500 g·mol -1 to 1,000,000 g·mol -1 , preferably in the range of 500 g·mol -1 to 500,000 g·mol -1 , and preferably in the range of 500 g·mol -1 to 100,000 g·mol -1 of the weight-average molecular weight.

[0239] According to a specific embodiment of the present invention, the (poly)amine compound is a monoamine compound and is selected from polydialkylsiloxanes, especially polydialkylsiloxanes of formula (IV)

[0240] H2N-ALK-Si(R’2)(R’3)-O-[Si(R’2)(R’3)-O] n -Si(R’2)(R’3)-R’4(IV)

[0241] In formula (IV), ALK represents a straight-chain or branched, preferably straight-chain (C1-C4) alkylene group such as propylene, R’2 and R’3 may be the same or different, preferably the same, and represent a (C1-C4) alkyl group such as methyl, and R’4 represents a straight-chain or branched (C1-C6) alkyl group, preferably a C4 group such as n-butyl, and n represents an integer greater than or equal to 2; preferably, the value of n is such that the weight-average molecular weight of the polydimethylsiloxane ranges from 500 to 3000 g·mol -1 . As examples of the polydimethylsiloxane (IV), mention may be made of the products sold by Gelest under the names MCR-A11 and MCR-A12.

[0242] According to a specific embodiment of the present invention, the (poly)amine compound is a diamine compound, that is, they contain two primary and / or secondary amine groups, preferably primary amine groups (NH2). More particularly, they are selected from the compounds of formula (V) and (VI):

[0243] ALK[(O-ALK’) m -NH2]2(V) or

[0244] H2N-ALK-Si(R’)2-[O-Si(R’)2]m -O-Si(R)2-ALK’-NH2 (VI)

[0245] In formulas (V) and (VI), ALK and ALK’ may be the same or different and represent a straight-chain or branched, preferably straight-chain (C1-C6) alkylene group such as propyl, R’ may be the same or different and represent a (C1-C4) alkyl group such as methyl, and m represents an integer greater than or equal to 0; preferably, the value of m is such that the weight-average molecular weight of compound (V) or (VI) ranges from 500 g.mol -1 to 55000 g.mol -1 . As examples of compounds of formula (VI), mention may be made of those sold by GEST with the names DMS-A11, DMS-A12, DMS-A15, DMS-A21, DMS-A31, DMS-A32 and DMS-A35.

[0246] The (poly)amine compounds which are diamines are in particular especially the polyether diamines of the formula H2N-ALK-O-[ALK’-O] m -ALK”-NH2, where ALK, ALK’ and ALK” may be the same or different and represent a straight-chain or branched (C1-C6) alkylene group, and m represents an integer greater than or equal to 0, such as 4,7,10-trioxa-1,13-tridecanediamine or especially the compounds known under the index number Jeffamine from Huntsman, and more particularly α,ω-diamino polyethylene glycol and / or polypropylene glycol (with amine functional groups at the ends of the chains), such as the products sold under the names Jeffamine D-230, D-400, D-2000, D-4000, ED-600, ED-9000 and ED-2003.

[0247] According to a specific embodiment of the present invention, the (poly)amine compounds are triamine compounds, i.e. they contain three primary and / or secondary amine groups, preferably primary amine groups (NH2). More particularly, especially the polyether triamines of the formula ALK”’[(O-ALK’) m -NH2]3, where ALK’ is as previously defined and ALK”’ represents a straight-chain or branched trivalent (C1-C6) alkylene group, and m represents an integer greater than or equal to 0.

[0248] As (poly)amine compounds which are triamine compounds, mention may in particular be made of polyether triamines, especially the polyether triamines of the formula known under the name Jeffamine from Huntsman; and especially α,ω-diamino polyethylene glycol and / or polypropylene glycol (with amine functional groups at the ends of the chains), such as the product sold under the name Jeffamine T-403.

[0249] As (poly)amine compounds that are triamine compounds, polyethertriamines can be specifically mentioned, and in particular α,ω-diaminopolyethylene glycol and / or polypropylene glycol (with amine functional groups at the ends of the chains), such as the product sold under the name Jeffamine T-403.

[0250] According to another specific embodiment of the present invention, the (poly)amine compound contains more than three primary and / or secondary amine groups, preferably primary amine groups (NH2).

[0251] In this variant, the (poly)amine compound is selected from poly(meth)acrylates or poly(meth)acrylamides carrying primary or secondary amine side functional groups, such as poly(3-aminopropyl)methacrylamide and poly(2-aminoethyl)methacrylate.

[0252] Preferably, the (poly)amine compound is selected from chitosan (especially poly(D-glucosamine)) and polydimethylsiloxanes containing primary amine groups at the ends and / or on the side chains.

[0253] According to this variant, the (poly)amine compound is particularly selected from poly((C2-C5)alkyleneimines), and preferably polyethyleneimine and polypropyleneimine, especially poly(ethyleneimine), in particular the product sold by Aldrich Chemical under the index number 408700 or by BASF under the trade name Lupasol, especially having a molecular weight of 1200 to 25,000; poly(allylamine), especially the product sold by Aldrich Chemical under the index number 479136; polyvinylamine and its copolymers, especially copolymers with vinylamides, especially vinylamine / vinylformamide copolymers, such as those sold by BASF under the name 9030; polyamino acids containing NH2 groups, such as polylysine, especially the product sold by JNC Corporation (formerly known as Chisso Corporation); aminodextran, especially the product sold by CarboMer Inc; aminopolyvinyl alcohol, especially the product sold by CarboMer Inc; copolymers based on acrylamido(C1-C6)alkylamines, especially copolymers based on acrylamidopropylamine; and poly(D-glucosamine), for example sold by Kytozyme Corporation under the index number Kionutrime sold.

[0254] According to one embodiment, the polydimethylsiloxane containing primary amine groups at the ends and / or on the side chains is selected from the following formula (VII):

[0255] R a -Si(R b )(R c)-O-[Si(R b )(R c )-O] m -[Si(ALK 1 -NH2)(R a )-O] n -Si(R b )(R c )-R a (VII)

[0256] In formula (VII), R a may be the same or different and represents a hydroxyl group or a (C1-C4) alkyl group, R b and R c may be the same or different, preferably the same, and represent a (C1-C4) alkyl group such as methyl, ALK 1 represents a straight-chain or branched (C1-C6) alkylene group, optionally inserted with an N(H) group, and m and n are integers greater than or equal to 1; preferably, m and n are such that the weight-average molecular weight of the compound of formula (VII) ranges from 1000 g·mol -1 to 500,000 g·mol -1 .

[0257] According to a preferred variant, formula (VII) is such that: R a , R b and R c represent methyl, ALK 1 represents propylene, and the values of n and m are such that the weight-average molecular weight of the polydimethylsiloxane ranges from 1000 g·mol -1 to 55,000 g·mol -1 . As examples of the polydimethylsiloxane of formula (VI), mention may be made of those sold by GEIST under the names AMS-132, AMS-152, AMS-162, AMS-163, AMS-191, and AMS-1203.

[0258] According to another variant, formula (VII) is such that: R a represents a hydroxyl group or a (C1-C4) alkyl group such as methyl, ALK 1 represents a (C5-C6) alkylene group substituted by an NH group; preferably, ALK 1 represents -(CH2)3-N(H)-(CH2)2-, and m and n are such that the weight-average molecular weight of the compound of formula (VI) ranges from 5000 g·mol -1 to 500,000 g·mol -1 .

[0259] As amine polymers, α,ω-diaminopoly(tetrahydrofuran) (or polytetramethylene glycol) and α,ω-diaminopolybutadiene may also be mentioned.

[0260] According to a specific embodiment of the invention, the (poly)amine compound is selected from hyperbranched polymers containing at least one amino group and dendrimeric polymers carrying at least one amino group, such as PAMAM polyamide amine dendrimer having an ethylenediamine core and terminal amine functional groups.

[0261] Thus, according to a preferred embodiment, the composition according to the invention comprises a crosslinking agent R selected from (poly)amine compounds, particularly selected from chitosan, aminoalkoxysilanes, polydimethylsiloxanes containing primary amine groups at the end of the chain or in the side chain, ammonia-terminated polydimethylsiloxanes, polyglucosamine, and mixtures thereof.

[0262] More preferably, the composition according to the invention comprises a crosslinking agent R selected from spermidine, aminoalkoxysilanes and polydialkylsiloxanes containing primary amine groups at the end of the chain or in the side chain, and even more preferably selected from 3-aminopropyltriethoxysilane (APTES), 3-aminoethyltriethoxysilane (AETES), 3-aminopropylmethyldiethoxysilane, N-(2-aminoethyl)-3-aminopropyltriethoxysilane and polydimethylsiloxane containing terminal aminopropyl groups at the end of the chain, and even more preferably 3-aminopropyltriethoxysilane (APTES) or its oligomers.

[0263] B) (Poly)thiol compound

[0264] According to a preferred embodiment, the crosslinking agent R is selected from (poly)thiol compounds, also known as "(poly)mercapto" compounds.

[0265] (Poly)thiol compounds may be particularly organic or inorganic, preferably organic.

[0266] In a preferred embodiment, the (poly)thiol compound is silicon-based, i.e., it contains one or more thiol groups and it also contains at least one siloxane chain.

[0267] In a specific embodiment, the (poly)thiol compound is inorganic. Polythiol silicone may be mentioned, for example.

[0268] The (poly)thiol compound for use in the composition according to the invention may be particularly selected from non-polymeric (poly)thiol compounds.

[0269] For the purposes of the present invention, the term "non-polymeric compound" means a compound that is not obtained directly via monomer polymerization reaction.

[0270] According to one embodiment of the present invention, the (poly) thiol compound is organic, non-polymeric and has the following formula (VIII), as well as its solvates such as hydrates:

[0271] L(SH) q (VIII)

[0272] In formula (VIII):

[0273] -q represents an integer greater than or equal to 2; preferably, n is from 2 to 10 and preferably from 2 to 5 including the end values;

[0274] -L denotes a saturated or unsaturated straight-chain or branched-chain, or saturated or unsaturated (hetero) cyclic polyvalent (at least divalent) group, which particularly contains 1 to 500 carbon and / or silicon atoms, more particularly 2 to 40 carbon and / or silicon atoms, even more particularly 3 to 30 carbon and / or silicon atoms, preferably 6 to 20 carbon atoms;

[0275] L is optionally inserted with and / or capped with: one or more heteroatoms or groups selected from O, S, N, Si and C(X) and their combinations, such as -O-, -O-C(X)-, -N(R)-C(X)- or -Si(R c )(R d )-O-, where R represents a hydrogen atom or a (C1-C6) alkyl such as methyl; and / or

[0276] L is optionally substituted with one or more groups selected from:

[0277] -N(R a )R b and -(X’) a -C(X)-(X”) b -R a ;

[0278] where X, X' and X” may be the same or different and represent an oxygen or sulfur atom, or a group N(R b )); a and b are equal to 0 or 1; preferably, the sum of a + b is equal to 1;

[0279] R a and R b may be the same or different and represent a hydrogen atom or a (C1-C6) alkyl or aryl (C1-C4) alkyl such as benzyl, preferably R a and R b represent a hydrogen atom; and R c and R d may be the same or different and represent a (C1-C6) alkyl, aryl (C1-C4) alkyl or (C1-C6) alkoxy group.

[0280] According to a specific embodiment of the present invention, the (poly)thiol compound is selected from polythiol compounds, in particular polythiol compounds containing 2 to 20 carbon atoms.

[0281] According to a preferred embodiment, the (poly)thiol compound is non-polymeric and in particular has the formula (VIII) as defined above, where q is an integer greater than or equal to 2, and preferably p is an integer from 2 to 10, and preferably from 2 to 5 and including the end values.

[0282] The (poly)thiol compound suitable for the present invention is preferably a dithiol compound.

[0283] Preferably, L denotes a C8-C 18 polyvalent group, which is in particular linear. Preferably, the fat-soluble polythiol is in particular a linear C8-C 18 dithiol. Advantageously, the C8-C 18 chain is a hydrocarbon chain, i.e. formed by carbon and hydrogen. In particular, the fat-soluble polythiol is a linear C8-C 16 and in particular a C 10 -C 14 dithiol. As the (poly)thiol compound of formula (VII), 1,8-octanedithiol, 1,10-decanedithiol, 1,12-dodecanedithiol, 1,14-tetradecanedithiol, 1,16-hexadecanedithiol and 1,18-octadecanedithiol may be more particularly mentioned. 1,10-Decanedithiol, 1,12-dodecanedithiol or 1,14-tetradecanedithiol is preferably used, and preferably 1,12-dodecanedithiol.

[0284] According to another specific embodiment of the present invention, the (poly)thiol compound is selected from thiolated alkoxysiloxanes, such as those of the following formula (VIII’): R’1-Si(OR’2)z(R’3) x (VIII’)

[0285] In formula (VIII’):

[0286] · R'1 is a linear or branched, saturated or unsaturated, cyclic or acyclic C1-C hydrocarbon chain substituted by one or more groups selected from the following groups: 12 hydrocarbon chains:

[0287] - thiol, and

[0288] - aryl, aryloxy, arylthio or arylamino, the aryl being substituted by one or more thiols or thio(C1-C6)alkyls, preferably thio(C1-C6)alkyl, and

[0289] -R'1 is optionally inserted with one or more heteroatoms such as O, S, N, carbonyl C(O), or a combination thereof such as ester -C(O)-O- or amide -C(O)-NH- in its hydrocarbon chain, and R'1 is directly bonded to the silicon atom via a carbon atom.

[0290] ·R'2 and R'3 may be the same or different and represent a straight-chain or branched-chain alkyl group containing 1 to 6 carbon atoms, preferably 1 to 4 carbon atoms, such as methyl.

[0291] ·z indicates an integer ranging from 1 to 3, and

[0292] ·x indicates an integer ranging from 0 to 2, where z + x = 3.

[0293] Preferably, R’2 represents a straight-chain or branched-chain, preferably straight-chain alkyl group containing 1 to 4 carbon atoms, such as ethyl.

[0294] Preferably, R’3 represents a straight-chain or branched-chain, preferably straight-chain alkyl group containing 1 to 4 carbon atoms, such as methyl or ethyl.

[0295] Preferably, R’1 is an acyclic chain. In particular, R’1 is a straight-chain or branched-chain, saturated or unsaturated, preferably saturated C1-C6 hydrocarbon chain, which is substituted by one or more thiol groups, preferably by one thiol group.

[0296] Preferably, R’1 is a saturated straight-chain C1-C6 hydrocarbon chain substituted by a thiol group, and R'2 represents an alkyl group containing 1 to 4 carbon atoms.

[0297] R'3 represents an alkyl group containing 1 to 4 carbon atoms. Preferably, z is equal to 3.

[0298] According to a more specific embodiment of the present invention, the thiolated alkoxysiloxane is selected from those of the following formula (IX):

[0299] (R 1 O)(R 2 )(R 3 )Si-[CH(R 4 )] t -[N(R’ 4 )-L 1 p -SH (IX)

[0300] In formula (IX):

[0301] ·p is 0 or 1; and t is an integer ranging from 1 to 4, preferably 2;

[0302] ·R 1 represents (C1-C6) alkyl;

[0303] ​·R 2 and R 3 may be the same or different, preferably the same, and are selected from:

[0304] -(C1-C6)alkyl, especially C1-C4 alkyl such as methyl;

[0305] -(C1-C6)alkoxy, especially (C1-C4)alkoxy such as methoxy;

[0306] ·R 4 and R’ 4 may be the same or different and represent a hydrogen atom or a (C1-C6)alkyl group, such as methyl;

[0307] ·L 1 represents a divalent saturated straight-chain or branched C1-C 20 hydrocarbon group.

[0308] According to a specific embodiment of the present invention, the mercaptoalkoxysiloxane is selected from those of the following formula (IX’):

[0309] (R’ 1 O)(R’ 2 )(R’ 3 )Si-CH(R 4 )-CH(R 5 )-(L 2 ) q -SH (IX’)

[0310] In formula (IX’):

[0311] ·q is 0 or 1;

[0312] ·X represents an oxygen or sulfur atom, preferably a sulfur atom;

[0313] ·R' 1 denotes a (C1-C6)alkyl group;

[0314] ·R' 2 and R' 3 may be the same or different, preferably the same, and are selected from:

[0315] -(C1-C6)alkoxy, especially C1-C4;

[0316] -(C1-C6)alkyl;

[0317] ·R 5 represents a hydrogen atom or a C1-C4 alkyl group optionally substituted with an amino group, a mercapto group or a hydroxyl group;

[0318] ·R 4 represents a hydrogen atom or a C1-C4 alkyl group, especially methyl;

[0319] ·L 2 represents a linear or branched, saturated C1-C 20 divalent hydrocarbon group which is optionally inserted with heteroatoms such as -N(H)-, and / or is optionally substituted with one or more hydroxyl groups, thiol groups or amino groups.

[0320] Preferably, the thiolated alkoxysilane is selected from 4-(trimethoxysilyl)-1-butanol, 3-(trimethoxysilyl)-1-propanol, 3-(triethoxysilyl)-1-propanol, 11-(trimethoxysilyl)-1-undecanethiol, 4-(trimethoxysilyl)-2-butanethiol, 2-(triethoxysilyl)ethanethiol, 3-(triethoxysilyl)-1-propanethiol, 2-(trimethoxysilyl)ethanethiol, 3-(trimethoxysilyl)-1-propanethiol and 3-(dimethoxymethylsilyl)-1-propanethiol.

[0321] More preferably, the thiolated alkoxysilane is selected from 2-(triethoxysilyl)ethanethiol (18236-15-2) and 3-(triethoxysilyl)-1-propanethiol (14814-09-6).

[0322] According to a preferred embodiment of the present invention, the (poly)thiol compound is selected from polymer (poly)thiol compounds.

[0323] The polymer (poly)thiol compound can be a star-shaped, comb-shaped, brush-shaped and dendritic homopolymer or copolymer carrying hydroxyl and / or thiol units. These polymers can be of natural origin, such as polysaccharides or polypeptides, or of synthetic origin, such as acrylic polymers, polyesters or polyglycols. The thiol units can be present as end groups or side groups.

[0324] Examples that can be mentioned include the polymers described in the following scientific articles: Polymers containing groups of biological activity [Polymers containing groups of biological activity], C.G. Overberger et al., Brooklyn Polytechnic Institute,

[0325] http: / / pac.iupac.org / publications / pac / pdf / 1962 / pdf / 0402x0521.pdf; EP 1247 515A2; US 3 676 440; and EP 1 572 778.

[0326] The polymer (poly)thiol compound of the present invention is preferably an organic and / or silicone compound, more preferably of formula (X): POLY(SH) q (X)

[0327] In formula (X):

[0328] · q is greater than or equal to 2, preferably greater than or equal to 3;

[0329] · POLY denotes a polymer group, which is preferably carbon-based or silicon-based;

[0330] POLY is optionally inserted with one or more heteroatoms or groups selected from O, S, N, Si and C(X) and combinations thereof, such as -O-, -O-C(X)-, -N(R)-C(X)- or -Si(R c )(R d )-O-, where R represents a hydrogen atom or a (C1-C6) alkyl group such as methyl; and / or

[0331] POLY is optionally substituted with one or more halogen atoms or groups selected from R a (R b )N- and -(X') a -C(X)-(X”) b -R a ;

[0332] -X, X' and X” may be the same or different and represent an oxygen or sulfur atom, or a group N(R b );

[0333] -a and b are equal to 0 or 1; preferably, the sum of a + b is equal to 1;

[0334] -R a and R b may be the same or different and represent a hydrogen atom or a (C1-C 10 ) alkyl group or an aryl(C1-C4) alkyl group such as benzyl; preferably, R a and R b represent a hydrogen atom; and

[0335] -R c and R d may be the same or different and represent a (C1-C 10 ) alkyl group, an aryl(C1-C4) alkyl group or a (C1-C 10 ) alkoxy group.

[0336] Methods for preparing the polymeric (poly) thiol compounds used according to the present invention are known to those skilled in the art; several methods are reported below in a non-limiting manner. The polymeric (poly) thiol compounds used according to the present invention can be obtained by polymerization or polycondensation of monomer units carrying thiol or protected thiol functional groups, optionally as copolymerization or co-polycondensation with monomer units free of thiol or protected thiol functional groups.

[0337] According to one embodiment of the present invention, the polymeric (poly) thiol compound used according to the present invention is a polymer soluble in a cosmetic medium, especially an aqueous or water-alcohol medium. They are more preferably obtained from amino polymers and their ammonium salts or from polyhydroxylated polymers.

[0338] According to another embodiment of the present invention, the thiolated polymer used according to the present invention is a polymer soluble in a lipophilic medium.

[0339] According to one embodiment of the present invention, the polythiol compound is a polymeric compound of formula (X), where q denotes an integer greater than or equal to 2, and POLY denotes a polymeric group based on carbon and / or silicon, preferably a silicon-based polymeric group. POLY may also contain one or more heteroatoms selected from O, N or S and / or one or more functional groups selected from (thio) ester, (thio) ketone, (thio) amide, (thio) urea and (thio) carbamate functional groups, and / or may be substituted by one or more linear or branched (C1-C 10 ) alkyl or linear or branched (C1-C 10 ) alkoxy groups, it being understood that when POLY is substituted, the thiol functional group may be carried by the substituent.

[0340] The weight average molecular weight of the polythiol polymer compounds (such as those of formula (X)) is generally from 500 to 400 000 g.mol -1 and preferably from 500 to 150 000 g.mol -1 . According to a specific embodiment of the present invention, the polythiol compound is selected from polyorganosiloxanes containing thiol groups on the end chains, such as those of formula (XI):

[0341] HS-L 4 -Si(R a )(R b )-O-[Si(R a )(R b )-O] n -Si(R a )(R b )-L 5 -SH (XI)

[0342] In formula (XI):

[0343] ·R a and R bmay be the same or different, preferably the same, and represents a group selected from: (C1-C4) alkyl such as methyl, (C1-C4) alkoxy such as methoxy, aryl such as phenyl, aryloxy such as phenoxy, aryl(C1-C4) alkyl such as benzyl, or aryl(C1-C4) alkoxy such as benzyloxy, preferably (C1-C4) alkyl such as methyl,

[0344] ·n represents an integer greater than or equal to 1, and more particularly, the value of n is such that the weight-average molecular weight of the silicone ranges from 500 to 55,000 g / mol -1 ; in particular, n is an integer in the range of 1 to 100, preferably in the range of 5 to 50 and preferably in the range of 10 to 30, and

[0345] ·L 4 and L 5 may be the same or different, preferably the same, and represents a straight-chain or branched-chain, saturated or unsaturated, optionally cyclic hydrocarbon chain containing 1 to 100 carbon atoms, optionally interrupted by one or more heteroatoms such as oxygen, sulfur or nitrogen, especially oxygen, and in particular represents a covalent bond or (C1-C6) alkylene, (C1-C6) alkoxy, oxy(C1-C6) alkylene, (C1-C6) alkoxy(C1-C6) alkylene, (C1-C6) alkoxy(C1-C6) alkoxy or oxy(C1-C6) alkoxy(C1-C6) alkylene, preferably (C1-C6) alkylene, (C1-C6) alkoxy, oxy(C1-C6) alkylene or (C1-C6) alkoxy(C1-C6) alkylene.

[0346] Preferably, the (poly) thiol compound is a polythiol polyorganosiloxane, more preferably a polythiol polydimethylsiloxane, especially those selected from formula (XII):

[0347] HS-L 4 -Si(CH3)2-O-[Si(CH3)2-O] n -Si(CH3)2-L 5 -SH (XII)

[0348] In formula (XII):

[0349] ·L 4 and L 5 are as previously defined in formula (XI), in particular, L 4 and L 5represents a (C1-C6) alkylene, (C1-C6) alkyleneoxy, oxy(C1-C6) alkylene or (C1-C6) alkyleneoxy(C1-C6) alkylene, more preferably a divalent group selected from -R2-, -O-R2-, -R2-O- and -R2-O-R2-, preferably -R2-O-R2-, where R2 represents a straight-chain or branched, preferably straight-chain, (C2-C6) alkylene such as ethylene or propylene, preferably n-propylene; and

[0350] · n is as defined in formula (XI).

[0351] As the polythiol compound of formula (XII), mention may be made of mercapto siloxanes or thiolated siloxanes in which the thiol functional group is at the chain end, sold by Shin-Etsu under the index number X-22-167B, and mercapto siloxanes in which the thiol functional group is in the side chain, sold by Shin-Etsu under the index number KF-2001, or polydimethylsiloxanes in which the thiol functional group is at the chain end (80 - 120 groups) via thio-n-propyl, sold by Gelest under the name DMS-SM 21.

[0352] Preferably, the polythiol compound is a polyorganosiloxane containing thiol groups in the side chain, such as those of formula (XIII):

[0353] R a -Si(R b )(R d )-O-[Si(R a )(R b )-O] m -[Si(R b )(ALK1-SH)-O] n -Si(R b )(R d )-R a (XIII)

[0354] In formula (XIII):

[0355] · R a and R b are as defined in formula (XI), and R d is as defined for R a and R b , preferably R a , R b and R d are the same and represent a (C1-C6) alkyl, such as methyl;

[0356] · R dIt may also represent a (C1-C6) alkyl group, preferably a (C1-C4) alkyl group such as methyl, substituted by a (C1-C4) alkylamino or amino or thiol group;

[0357] · ALK1 represents a straight-chain or branched-chain, optionally cyclic, saturated or unsaturated divalent hydrocarbon radical chain containing 1 to 100 carbon atoms, optionally interrupted by one or more heteroatoms such as oxygen, sulfur or nitrogen (especially O), a (thio)carbonyl C(X) (where X represents O or S), or a combination thereof, such as -O-, -O-C(O)- or -C(O)-O-; preferably, ALK1 represents a (C1-C6) alkylene group, and more preferably a (C1-C4) alkylene group such as propylene;

[0358] · n and m may be the same or different, represent integers greater than 2, and more particularly the values of m and n are such that the weight-average molecular weight of the polyorganosiloxane is from 1000 to 55000 g / mol -1 ;

[0359] As examples of the polythiol compounds of formula (XIII), mention may be made of those sold by Genesee Polymers under the names GP-367, GP-71-SS, GP-800 and GP-710s, preferably GP-367 sold by Genesee Polymers.

[0360] The polythiol compounds are especially polydimethylsiloxanes containing at least two thiol groups, such as the products SMS-022, SMS-042 and SMS-992 sold by Gelest at https: / / www.gpcsilicones.com / products / silicone-fluids / mercapto-functional, https: / / www.shinetsusilicone-global.com / products / type / oil / detail / search / deg07.shtml and 1053_Reactive Silicones_Silanes / Silicones-Gelest.

[0361] According to a specific embodiment of the present invention, the (poly)thiol compound is selected from hyperbranched polymers containing at least one thiol group and dendritic polymers carrying at least one thiol group, such as thiolated PAMAM dendrimers.

[0362] Preferably, the (poly)thiol compound used according to the present invention is selected from polydiallylsiloxanes containing at least two thiol groups, especially polydimethylsiloxanes, such as those of formula (XIII).

[0363] C) (Poly)carbonyl compound

[0364] According to a specific embodiment, the crosslinking agent R is a (poly)carbonyl compound.

[0365] In particular, the (poly)carbonyl compound is selected from terephthalaldehyde, 5,5-dimethyl-1,3-cyclohexanedione, phenylglyoxal, isophthalaldehyde, 4-acetylbenzaldehyde, 4,4'-diformyltriphenylamine, 2-acetylbenzaldehyde, 3-(2-furoyl)quinoline-2-carbaldehyde, 3-(2-furoyl)quinoline-2-carbaldehyde, 3-acetylbenzaldehyde, 9-(2-ethylhexyl)carbazole-3,6-dicarbaldehyde, phthalaldehyde, 1,3-cyclohexanedione, 4,4'-biphenyldicarbaldehyde, benzene-1,3,5-tricarbaldehyde, and nonionic or anionic oxidized polysaccharides such as oxidized inulin, especially those of formula (II) as defined below. In particular, the (poly)carbonyl compound includes saturated or unsaturated aromatic C5-C7 carbocycles, preferably aromatic ones such as phenyl, or non-aromatic and saturated ones such as cyclohexyl, more preferably unsaturated and aromatic ones such as terephthalaldehyde.

[0366] According to a specific embodiment, the (poly)carbonyl compound is selected from nonionic or anionic oxidized polysaccharides containing one or more aldehyde groups and optionally one or more anionic groups.

[0367] These anionic groups are preferably carboxyl or carboxylate groups.

[0368] The nonionic or anionic oxidized polysaccharide according to the present invention can be represented by the following formula (II): P-(CHO) m (COOQ) n (II)

[0369] In formula (II):

[0370] ·P represents a polysaccharide chain preferably composed of monosaccharides containing 5 carbon atoms or more than 5 carbon atoms, preferably 6 or more carbon atoms and more particularly 6 carbon atoms;

[0371] ·Q is selected from a hydrogen atom, ions derived from: alkali metals or alkaline earth metals such as sodium or potassium, ammonia, organic amines such as monoethanolamine, diethanolamine, triethanolamine and 3-amino-1,2-propanediol, and basic amino acids such as lysine, arginine, glycine, ornithine and citrulline;

[0372] ·m + n is greater than or equal to 1,

[0373] ·m is such that the degree of substitution (DS(CHO)) of the polysaccharide substituted by one or more aldehyde groups is in the range of 0.001 to 2 and preferably 0.005 to 1.5;

[0374] · n is the degree of substitution (DS(COOX)) by means of which the polysaccharide is substituted by one or more carboxyl groups and is in the range from 0 to 2 and preferably from 0.001 to 1.5.

[0375] The expression “degree of substitution DS(CHO) or DS(COOX) of the polysaccharide according to the invention” means the ratio between the number of carbons which are oxidized to aldehyde or carboxyl groups for all the repeating units and the number of basic monosaccharides constituting the polysaccharide (even after ring opening by pre-oxidation). The groups CHO and COOX can be obtained during the oxidation of certain carbon atoms of the sugar units containing 6 carbon atoms (such as carbon atoms 2, 3 or 6).

[0376] Preferably, the oxidation can be carried out on carbons 2 and 3, more particularly in a proportion of 0.01% to 75% and preferably 0.1% to 50% relative to the number of rings which may have been opened.

[0377] The polysaccharide chain represented by P is preferably selected from cellulose, starch, maltodextrin, guar gum, xanthan gum, pullulan, agarose, carrageenan, gellan gum, gum arabic, polyxylan and tragacanth gum, and derivatives thereof.

[0378] The term “derivatives” means compounds obtained by chemical modification of the compounds mentioned. They can be esters, amides or ethers of said compounds.

[0379] The oxidation can be carried out according to methods known in the art, for example according to the methods described in FR 2 842 200, document FR 2 854161 or the article by E. Fredon et al., “Hydrophobic films from maize bran hemicelluloses”, Carbohydrate Polymers 49, pages 1 to 12 (2002).

[0380] Another oxidation method is described in the article “Water soluble oxidized starches by peroxidereaction extrusion”, Industrial Crops and Products 7, R.E. Wing, J.L. Willet, 45 - 52 (1997).

[0381] According to this embodiment, the (poly)carbonyl compound associates in its implementation with an amine catalyst, as described in Progress in coating 129, 21 - 25 (2019) and Progress in coating 135, 510 - 516 (2019); preferably, the amine catalyst is selected from piperidine, DMAP (dimethylaminopyridine), DBU (1,8 - diazabicyclo[5.4.0]undec - 7 - ene), DABCO (1,4 - diazabicyclo[2.2.2]octane), and DBN (1,5 - diazabicyclo[4.3.0]non - 5 - ene), more preferably selected from DBU (1,8 - diazabicyclo[5.4.0]undec - 7 - ene), DABCO (1,4 - diazabicyclo[2.2.2]octane), and DBN (1,5 - diazabicyclo[4.3.0]non - 5 - ene), and in particular, the catalyst is DBU (1,8 - diazabicyclo[5.4.0]undec - 7 - ene).

[0382] D) (Poly)acrylate compound

[0383] According to a specific embodiment, the cross - linker is a (poly)acrylate compound.

[0384] The term “(poly)acrylate” means a compound containing at least one acrylate group H2C═C(R e ) - C(O) - Y -, where R e represents a hydrogen atom or a (C1 - C4) alkyl group, such as methyl, preferably R e represents a hydrogen atom, and Y represents an oxygen atom or an amino group - N(H) -, preferably O.

[0385] More particularly, the (poly)acrylate of the present invention has the formula (XIV) L[-Y - C(O) - C(R e )═CH2] q (XIV)

[0386] In formula (XIV), q and L are as defined in formula (VIII); Y and R e are as previously defined, preferably Y = O and R e = H. According to a preferred embodiment, the compound of formula (XIV) is such that: L represents a divalent or trivalent, preferably trivalent, hydrocarbon chain containing 1 to 8 carbon atoms, q is 2 or 3, preferably 3, Y represents O, and R e represents a hydrogen atom.

[0387] According to a specific embodiment, the (poly)acrylate compound is selected from polyorganosiloxanes containing at least one acrylate group in the side chain, such as those of the following formula:

[0388] R a -Si(R b )(R d )-O-[Si(R a )(R b )-O] m -[Si(R b )(ALK1-Y-C(O)-C(R e )=CH2)-O] n -Si(R b )(R d )-R a (XV)

[0389] In formula (XV):

[0390] ·R a 、R b and R d are as defined for formula (XIII), and preferably represent (C1-C6) alkyl such as methyl,

[0391] ·ALK1 is as defined for formula (XIII), preferably, ALK1 represents (C1-C6) alkylene, more preferably (C1-C4) alkylene, such as propylene; and

[0392] ·n and m can be the same or different, represent integers greater than 2, and more particularly the values of m and n are such that the weight average molecular weight of the polyorganosiloxane is 1000 to 55000 g·mol -1 .

[0393] ·Y is as previously defined, preferably O.

[0394] More particularly, the (meth)acrylate compound can be selected from 1,3-butanediol diacrylate, 1,4-butanediol diacrylate, bis(trimethylolpropane) tetraacrylate, glycerol 1,3-diglyceride diacrylate, glycerol propoxylate (1PO / OH) triacrylate, 1,6-hexanediol diacrylate, 1,6-hexanediol ethoxylate diacrylate, hydroxypivaloyl hydroxypivalate, neopentyl glycol diacrylate, neopentyl glycol propoxylate (1PO / OH) diacrylate, pentaerythritol tetraacrylate, pentaerythritol triacrylate, poly(propylene glycol) diacrylate, tricyclo[5.2.1.02,6]decane dimethanol diacrylate, trimethylolpropane ethoxylate (1EO / OH) methyl ether diacrylate, trimethylolpropane propoxylate triacrylate, trimethylolpropane trimethacrylate, tris(propylene glycol) diacrylate, trimethylolpropane triacrylate and tris[2-(acryloyloxy)ethyl] isocyanurate.

[0395] (Poly)acrylate compounds may also be selected from N,N'-methylenebisacrylamide.

[0396] According to this embodiment, the (poly)acrylate compound is incorporated in its implementation with an amine catalyst, for example, as described in Progress in coating 129, 21-25 (2019) and Progress in coating 135, 510-516 (2019). Preferably, the amine catalyst is selected from piperidine, DMAP (dimethylaminopyridine), DBU (1,8-diazabicyclo[5.4.0]undec-7-ene), DABCO (1,4-diazabicyclo[2.2.2]octane), and DBN (1,5-diazabicyclo[4.3.0]non-5-ene), more preferably selected from DBU (1,8-diazabicyclo[5.4.0]undec-7-ene), DABCO (1,4-diazabicyclo[2.2.2]octane), and DBN (1,5-diazabicyclo[4.3.0]non-5-ene), and in particular, the catalyst is DBU (1,8-diazabicyclo[5.4.0]undec-7-ene).

[0397] More particularly, the (poly)acrylate compounds are selected from those of formula (XIV), especially trimethylolpropane triacrylate, and those of formula (XV), especially the copolymer of dimethylsiloxane and acryloxypropylmethylsiloxane.

[0398] E) Metal alkoxide

[0399] According to another specific embodiment, the crosslinking agent R is a compound selected from metal alkoxides of the following formula (XIV a ), (XIV b ), (XIV c ), and (XIV d ) and mixtures thereof:

[0400] M-(OR1) n (XIV a ) R-M-(OR1) n-1 (XIV b )

[0401] (R1O) n-1 -M-R”-M'-(OR1') n'-1 (XIV c ) R-M(R')-(OR1) n-2 (XIV d )

[0402] In formula (XIV a), (XIV b ), (XIV c ), and (XIV d ) where:

[0403] -M and M' can be the same or different and represent atoms selected from the group consisting of alkaline earth metals, transition metals, lanthanide family metals, post-transition metals such as aluminum or tin, and metalloids such as boron; preferably transition metals such as Ti and post-transition metals such as aluminum;

[0404] -n and n' respectively represent the valences of the atoms represented by M and M';

[0405] -R1 and R1' can be the same or different and represent straight-chain or branched, saturated or unsaturated hydrocarbon groups containing 1 to 30 carbon atoms, preferably 1 to 6 carbon atoms, optionally interrupted by 1 to 20 heteroatoms selected from O, N, S, and P, especially O or N; and / or the hydrocarbon group is optionally substituted by one or more hydroxyl or carbonyl groups;

[0406] -R and R' can be the same or different and represent a hydrogen atom or a straight-chain, branched, acyclic or cyclic, saturated or unsaturated hydrocarbon group containing 1 to 30 carbon atoms, preferably 2 to 20 carbon atoms, optionally interrupted by 1 to 20 heteroatoms selected from O, N, S, and / or P, especially O or N, and / or the hydrocarbon group is optionally substituted by one or more hydroxyl or carbonyl groups;

[0407] -R” represents -O-, -N(R2)-, -S- or a straight-chain, cyclic or branched, saturated or unsaturated divalent hydrocarbon group containing 1 to 30 carbon atoms, preferably 2 to 20 carbon atoms, optionally interrupted by 1 to 20 heteroatoms selected from O, N, S, and P, especially O or N, where R2 represents a straight-chain, cyclic or branched, saturated or unsaturated hydrocarbon group containing 1 to 30 carbon atoms, preferably 2 to 20 carbon atoms.

[0408] Preferably, M and M' can be the same or different and represent atoms selected from transition metals such as titanium or zirconium or alkaline earth metals such as magnesium, more preferably atoms selected from transition metals such as titanium or zirconium, even more preferably titanium.

[0409] Preferably, the organometallic compound is an alcoholate of the formula (XIV a ) as defined previously. According to this preferred embodiment, the organometallic compound is more particularly selected from alcoholates of the formula (XIV a ) where:

[0410] -M represents an atom selected from the group consisting of transition metals, lanthanide metals, post-transition metals such as aluminum, tin, metalloids such as boron, or alkaline earth metals such as magnesium or calcium;

[0411] -n represents the valence of the atom represented by M;

[0412] -R1 represents a straight-chain or branched-chain, saturated hydrocarbon group containing 1 to 30 carbon atoms, preferably 1 to 6 carbon atoms.

[0413] According to another more preferred embodiment, the organometallic compound is selected from alkoxides of formula (XIV a ), where M represents an atom selected from transition metals such as zirconium or titanium, lanthanide metals, post-transition metals such as aluminum or tin, metalloids such as boron, and alkaline earth metals such as magnesium, preferably M represents a titanium atom; n represents the valence of the atom represented by M, especially 1, 2, 3 or 4, especially 4; R1 represents methyl, ethyl, 2-ethylhexyl, propyl, isopropyl, n-butyl, isobutyl or tert-butyl. According to an even more preferred embodiment, the organometallic compound is selected from zirconium ethoxide (Zr(OC2H5)4), zirconium propoxide (Zr(OCH2CH2CH3)4), zirconium isopropoxide (Zr(OCH(CH3)2)4), zirconium butoxide Zr(OCH2CH2CH2CH3)4, zirconium tert-butoxide (Zr(OC(CH3)3)4), titanium ethoxide (Ti(OC2H5)4), titanium propoxide (Ti(OCH2CH2CH3)4), titanium isopropoxide (Ti(OCH(CH3)2)4), titanium butoxide (Ti(OCH2CH2CH2CH3)4), titanium tert-butoxide (Ti(OC(CH3)3)4), 2-ethylhexanol titanate (Ti(OCH2CH(C2H5)(CH2)3CH3)4), and mixtures thereof, more preferably selected from zirconium propoxide, titanium propoxide, titanium butoxide and mixtures thereof. More preferably, the crosslinking agent R is a compound of formula (XIV a ), preferably where M represents an atom selected from transition metals, especially titanium, such as titanium butoxide.

[0414] According to a preferred embodiment, the crosslinking agent is selected from A) (poly)amine compounds, B) (poly)thiol compounds, C) (poly)carbonyl compounds, D) (poly)acrylate compounds, E) metal alkoxides, and preferably selected from A) (poly)amine compounds and B) (poly)thiol compounds.

[0415] In particular, the (poly)amine compound A) is selected from a) chitosan, such as poly(D-glucosamine), b) polyether diamines, in particular α,ω-diamino polyethylene glycol (carrying amine functional groups at the ends of the chains) and 4,7,10-trioxa-1,1-tridecanediamine, c) polyether triamines, such as polyetheramines (or Jeffamines), d) aminoalkoxysilanes, such as APTES, e) polydialkylsiloxanes containing primary amine groups at the ends or on the side chains, in particular polydimethylsiloxanes containing primary amine groups, such as bis(3-aminopropyl)-terminated poly(dimethoxysiloxane) (PDMS-diNH2) and amino-terminated polydimethylsiloxanes containing amine groups on the side chains, such as bis(cetearyl)amino-terminated polydimethylsiloxane, f) polyamine alkanes, such as those of formula (XII’) H2N-Alk-NH2, where Alk is a (C1-C6) alkylene group optionally substituted by one or more amino groups and / or optionally interrupted by one or more -N(H)-, such as spermidine.

[0416] In particular, the (poly)thiol compound B) is selected from a) polydialkylsiloxanes carrying thiol functional groups, and b) alkoxysilanes carrying thiol functional groups, and is in particular selected from a) polydialkylsiloxanes carrying thiol functional groups, preferably polydimethylsiloxanes containing thiol groups (such as mercaptopropyl) on the side chains, in particular those of formula (XIII).

[0417] In particular, the (poly)acrylate compound D) is selected from those of formula (XIV), in particular trimethylolpropane triacrylate, and those of formula (XV), in particular copolymers of dimethylsiloxane and acryloxypropylmethylsiloxane, preferably trimethylolpropane triacrylate.

[0418] In particular, the metal alkoxide compound E) is selected from those of formula (XIVa), such as titanium butoxide.

[0419] iii) Cosmetic active agent

[0420] According to a particular embodiment, the method of the invention uses one or more active agents for caring for keratin fibers.

[0421] More particularly, in the method of the invention, according to one embodiment, at least one of the compositions C1, C2, C3, C4 or C5 used contains one or more active agents for caring for keratin fibers, the proportion of which is preferably at least 0.01% by weight relative to the total weight of the composition under consideration. In particular, the caring active agent can be at least one hydrophilic active agent and / or one lipophilic active agent, and preferably a hydrophilic caring active agent.

[0422] The term "hydrophilic active agent" means a water-soluble or water-dispersible active agent capable of forming hydrogen bonds.

[0423] According to a specific embodiment of the method for treating keratin fibers according to the present invention, the compositions C1, C2, C3, C4 or C5 use one or more cosmetic active agents. In particular, the cosmetic active agents of the present invention are selected from a) colorants (or colorants) selected from pigments, direct dyes and mixtures thereof, b) active agents for caring for keratin fibers, preferably hair, c) UV screening agents, and d) mixtures thereof.

[0424] UV screening agent

[0425] According to one embodiment of the present invention, in the method of the present invention, at least one of the compositions C1, C2, C3, C4 or C5 used contains at least one UV screening agent as a cosmetic active agent. The UV screening agent is a UV screening agent commonly used in cosmetics. It can be selected from the positive list contained in Annex VI to Regulation (EC) No. 1223 / 2009, which specifies the list of UV screening agents permitted in cosmetics. The UV screening agents suitable for the present invention can have different properties. They can be lipophilic, hydrophilic or insoluble organic reagents.

[0426] The term "lipophilic UV screening agent" means any cosmetic or dermatological screening agent that can be completely dissolved in the liquid fat phase in molecular form or can be dissolved in the liquid fat phase in colloidal form (for example, in micellar form).

[0427] The term "hydrophilic UV screening agent" means any cosmetic or dermatological screening agent that can be completely dissolved in the liquid water phase in molecular form or can be dissolved in the liquid water phase in colloidal form (for example, in micellar form).

[0428] The term "insoluble UV screening agent" means any cosmetic or dermatological screening agent that is neither defined as a lipophilic UV screening agent nor as a hydrophilic UV screening agent and that is in particulate form in the aqueous phase or the liquid fat phase. The UV screening agents of the compositions according to the present invention can provide UVA and / or UVB light protection.

[0429] According to a preferred embodiment, the composition according to the present invention (which is preferably a cosmetic composition) can contain at least one organic and / or mineral UV screening agent (for screening out the UV radiation of sunlight).

[0430] In particular, the UV screening agent is selected from bis-resorcinol-based triazine derivatives, dibenzoylmethane derivatives, benzylidene camphor derivatives, and mixtures thereof. The organic UV screening agent may also be selected from anthranilic acid derivatives; cinnamic derivatives; salicylic acid derivatives; benzophenone derivatives; phenylbenzotriazole derivatives; benzylidene malonate derivatives, especially those mentioned in patent US 5,624,663; phenylbenzimidazole derivatives; imidazoline; 4,4-diarylbutadiene derivatives; bis-benzoxazolyl derivatives, as described in patents EP 669,323 and US 2,463,264; p-aminobenzoic acid (PABA) derivatives; methylene bis(hydroxyphenylbenzotriazole) derivatives, as described in patent applications US 5,237,071, US 5,166,355, GB 2,303,549, DE 197,26,184, and EP 893,119; benzoxazole compounds, as described in patent applications EP 0,832,642, EP 1,027,883, EP 1,300,137, and DE 101,62,844; screening polymers and screening silicones, especially those described in patent application WO 93 / 04665; dimers based on α-alkylstyrene, as described in patent application DE 198,55,649; 4,4-diarylbutadiene, as described in patent applications EP 0967,200, DE 197,46,654, DE 197,55,649, EP 1,008,586, EP 1,133,980, and EP 133,981; other merocyanine derivatives, as described in patent applications WO 04 / 006878, WO 05 / 058269, and WO 06 / 032741, and mixtures thereof.

[0431] According to a specific embodiment, the concentration range of the organic UV screening agent in the composition according to the present invention is from 1% to 50% relative to the total weight of the composition, preferably from 1% to 40% by weight, and even better, for example, in the range of 5% to 35% by weight.

[0432] The UV screening agent may be a mineral UV screening agent, which is usually a pigment. The pigment may or may not be coated.

[0433] Thus, the mineral UV screening agent may be selected from coated or uncoated pigments, and in particular from coated titanium oxide pigments, silicone-treated titanium oxide, uncoated titanium oxide pigments, uncoated zinc oxide pigments, coated zinc oxide pigments, uncoated cerium oxide pigments, uncoated iron oxide pigments, coated iron oxide pigments, and mixtures thereof.

[0434] According to specific embodiments, the compositions C1 to C5 according to the invention do not contain mineral UV screening agents.

[0435] According to specific embodiments, the amount of mineral UV screening agent present in the compositions according to the invention may range from 0.01% to 20% by weight relative to the total weight of the compositions C1 to C5 containing it. Its range is, for example, from 1% to 15% by weight relative to the total weight of the composition.

[0436] According to specific embodiments, at least one of the compositions C1 to C5 according to the invention further comprises one or more organic UV screening agents and one or more mineral UV screening agents.

[0437] According to specific embodiments, the compositions according to the invention comprise a combination of UV screening agents as described in patent FR 2 977490, patent application WO2013 / 004777 or patent application US2014 / 0134120.

[0438] According to specific embodiments, at least one cosmetic agent is selected from colorants, preferably selected from pigments, direct dyes and mixtures thereof, more preferably pigments.

[0439] Needless to say, the person skilled in the art will carefully select such or these optional cosmetic active agents, and / or their amounts, such that the advantageous properties of the corresponding compositions according to the invention are not or are substantially not adversely affected by the envisaged addition.

[0440] Dye

[0441] According to specific embodiments, the method according to the invention uses one or more colorants.

[0442] More particularly, in the method according to the invention, at least one of the compositions C1, C2, C3, C4 or C5 used comprises at least one particulate or non-particulate, water-soluble or water-insoluble colorant, preferably in a proportion of at least 0.01% by weight relative to the total weight of the composition under consideration. For obvious reasons, this amount can vary significantly with regard to the intensity of the desired color effect and the color strength provided by the colorant under consideration, and its adjustment undoubtedly falls within the capabilities of the person skilled in the art.

[0443] Preferably, composition C1, C2, C3, C4 or C5 comprises at least one colorant selected from pigments, direct dyes and mixtures thereof, more preferably a pigment; more preferably, the pigments of the present invention are selected from carbon black, iron oxide, especially yellow, red and black iron oxides, and mica coated with iron oxide, triarylmethane pigments, especially blue and purple triarylmethane pigments such as Lake Blue 1, azo pigments, especially red azo pigments such as D&C Red 7, alkali metal salts of lithol red such as calcium salt of lithol red B, and even more preferably red iron oxide, yellow iron oxide and azo pigments, especially red azo pigments such as SunPuro red iron oxide.

[0444] Pigment

[0445] For the purposes of the present invention, the term "pigment" means any compound capable of imparting color to keratin fibers. These compounds have a solubility in water at 25 °C and atmospheric pressure (760 mmHg) of less than 0.05% by weight, and preferably less than 0.01% by weight.

[0446] As pigments suitable for the present invention, mention may in particular be made of organic and / or mineral pigments known in the art, especially those described in Kirk-Othmer’s Encyclopedia of Chemical Technology and Ullmann’s Encyclopedia of Industrial Chemistry. These pigments may be synthetic or natural. These pigments may be in the form of pigment powders or pastes. They may be coated or uncoated. These pigments may be selected, for example, from mineral pigments, organic pigments, lakes, pigments with special effects such as mother-of-pearl or glitter flakes, and mixtures thereof.

[0447] The pigments suitable for the present invention may be selected from mineral pigments.

[0448] The term "mineral pigment" means any pigment that meets the definition in the chapter on inorganic pigments in Ullmann’s encyclopedia. Among the mineral pigments that can be used in the present invention, mention may be made of manganese violet, ultramarine blue, chromium hydrates, iron blue and titanium, zirconium or cerium oxides or dioxides, and also zinc, iron or chromium oxides.

[0449] Pigments with a possible structure such as sericite / brown iron oxide / titanium dioxide / silicon dioxide type are also possible. Such pigments are sold, for example, by Chemicals and Catalysts under the reference number Coverleaf NS or JS and have a contrast ratio in the range of 30. They can also be pigments with a structure that can be, for example, of the silica microsphere type containing iron oxide. An example of a pigment with this structure is the product sold by Miyoshi under the reference number PC Ball PC-LL-100P, which consists of silica microspheres containing yellow iron oxide.

[0450] Advantageously, the pigment may be iron oxide and / or titanium dioxide.

[0451] Pigments suitable for use in the present invention may be selected from organic pigments.

[0452] The term "organic pigment" refers to any pigment that meets the definition in the chapter on organic pigments in Ullmann's Encyclopedia. Among the organic pigments that can be used in the present invention, mention may be made of nitroso, nitro, azo, xanthene, pyrene, quinoline, anthraquinone, triphenylmethane, fluoran, phthalocyanine, metal complexes, isoindolinone, isoindolinone, quinacridone, peronone, perylene, diketopyrrolopyrrole, indigo, thioindigo, dioxazine, triphenylmethane and quinophthalone compounds. In particular, the white or colored organic pigment can be selected from carmine, carbon black, aniline black, azo yellow, quinacridone, phthalocyanine blue, blue pigments numbered in the Color Index with index numbers CI 42090, 69800, 69825, 74100, 74160, yellow pigments numbered in the Color Index with index numbers CI 11680, 11710, 19140, 20040, 21100, 21108, 47000, 47005, green pigments numbered in the Color Index with index numbers CI 61565, 61570, 74260, orange pigments numbered in the Color Index with index numbers CI11725, 45370, 71105, Red pigments numbered 12085, 12120, 12370, 12420, 12490, 14700, 15525, 15580, 15620, 15630, 15800, 15850, 15865, 15880, 26100, 45380, 45410, 58000, 73360, 73915, 75470, such as those obtained by oxidative polymerization of indole or phenol derivatives as described in patent FR 2 679 771.

[0453] Examples that may also be mentioned include pigment pastes of organic pigments, such as products sold by Hoechst under the following names: Cosmenyl Yellow IOG: Pigment Yellow 3 (CI 11710); Cosmenyl G yellow: Pigment Yellow 1 (CI 11680); Cosmenyl GR orange: Pigment Orange 43 (CI 71105); Cosmenyl R red: Pigment Red 4 (CI 12085); Cosmenyl FB carmine: Pigment Red 5 (CI 12490); Cosmenyl RL violet: Pigment Violet 23 (CI 51319); Cosmenyl A2R blue: Pigment Blue 15.1 (CI 74160); Cosmenyl GG green: Pigment Green 7 (CI 74260); Cosmenyl R black: Pigment Black 7 (CI 77266).

[0454] 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 in particular consist of particles that include an inorganic core, at least one binder for attaching the organic pigment to the core, and at least one organic pigment that at least partially covers the core.

[0455] The organic pigment can also be a lake.

[0456] The term "lake" means a dye adsorbed on an insoluble particle, and the assembly thus obtained remains insoluble during use.

[0457] Examples of inorganic substrates on which the dye is adsorbed are, for example, alumina, silica, calcium sodium borosilicate or calcium aluminium borosilicate and aluminium. Among the dyes adsorbed on organic substrates, carminic acid may be mentioned. Also mention may be made of dyes known under the following names: D&C Red 21 (CI 45 380), D&C Orange 5 (CI 45 370), D&C Red 27 (CI 45 410), D&C Orange 10 (CI 45425), 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 19140), D&C Yellow 6 (CI 15985), D&C Green 5 (CI 61 570), D&C Yellow 10 (CI 77 002), D&C Green 3 (CI 42 053), D&C Blue 1 (CI 42 090), FDC Red 4, D&C Red 6, D&C Red 22, D&C Red 28, D&C Red 30, D&C Orange 4, D&C Yellow 8, D&C Green 5, D&C Red 17, D&C Green 6, D&C Yellow 11, D&C Violet 2, Sudan Red, carotenoids (β-carotene, lycopene), xanthophylls (capsaicin, capsanthin, lutein), palm oil, Sudan Brown, quinoline yellow, annatto, curcumin, betanin (beet), carmine, copper chlorophyllin, methylene blue, anthocyanins (black rice purple (enocianine), black carrot, hibiscus, elderberry), riboflavin, beet juice and caramel.

[0458] Examples of lakes that may be mentioned are products known under the following names: D&C Red 7 (CI 15 850:1).

[0459] The pigment may also be a pigment with special effects.

[0460] The term "pigment with special effects" means a pigment that generally produces a non-uniform coloured appearance (characterized by a certain chromaticity, a certain vivacity and a certain brightness level) that varies with the observation conditions (light, temperature, viewing angle, etc.). Thus, they are different from coloured pigments that provide standard uniform opaque, translucent or transparent hues.

[0461] There are several types of pigments with special effects: those with a low refractive index, such as fluorescent or photochromic pigments, and those with a higher refractive index, such as nacre, interference pigments or glitter flakes.

[0462] The size of the pigments used in the compositions according to the invention is generally from 10 nm to 200 μm, preferably from 20 nm to 80 μm and more preferably from 30 nm to 50 μm.

[0463] The pigments may be dispersed in the composition by means of a dispersant.

[0464] The dispersant may be a surfactant, an oligomer, a polymer or a mixture of several thereof carrying one or more functional groups having a strong affinity for the surface of the particles to be dispersed. In particular, they may become physically or chemically attached to the surface of the pigment. These dispersants also contain at least one functional group that is compatible with or soluble in the continuous medium. In particular, polyols such as esters of 12-hydroxystearic acid of glycerol or diglycerol and C8 to C 20 Esters of fatty acids, such as poly(12-hydroxystearic acid) stearate with a molecular weight of about 750 g / mol, such as the product sold under the name Solsperse 21 000 by the company Avecia, polyglyceryl-2 dipolyhydroxystearate (CTFA name) sold under the reference Dehymyls PGPH by the company Henkel, or polyhydroxystearic acids such as the product sold under the reference Arlacel P100 by the company Uniqema, and mixtures thereof. As other dispersants that can be used in the composition of the invention, mention may be made of quaternary ammonium derivatives of polycondensed fatty acids, such as Solsperse 17 000 sold by Avecia, and polydimethylsiloxane / propylene oxide mixtures, such as those sold under the references DC2-5185 and DC2-5225 C by the company Dow Corning. The pigments used in the composition may be surface-treated with organic agents. According to a particular embodiment, the dispersant is of aminosilicone type other than the alkoxysilanes previously described, and is cationic. Preferably, the pigment is chosen from mineral pigments, mixed mineral-organic pigments, or organic pigments.

[0465] According to a specific embodiment, the pigment according to the invention is an organic pigment, preferably an organic pigment surface-treated with an organic agent chosen from silicone compounds.

[0466] According to another embodiment of the present invention, the pigment according to the present invention is a mineral pigment.

[0467] According to a particular embodiment of the invention, the cosmetic active agent is a coloring agent chosen from one or more direct dyes.

[0468] The term "direct dye" means natural and / or synthetic dyes, except oxidation dyes. These are dyes that will spread superficially on the fibers. They can be ionic or nonionic, preferably cationic or nonionic.

[0469] Among the direct dyes suitable for the present invention, azo direct dyes can be mentioned; (poly)methine dyes such as cyanines, hemicyanines and styryl types; carbonyl dyes; azine dyes; nitro(hetero)aryl dyes; tri(hetero)arylmethane dyes; porphyrin dyes; phthalocyanine dyes and natural direct dyes, either alone or in the form of a mixture.

[0470] The direct dye is preferably a cationic direct dye. Hydrazinium cation dyes of the following formulas (A) and (B) and azo cation dyes of the following formulas (C) and (D) can be mentioned:

[0471] Het + -C(Ra)=N-N(Rb)-Ar,Q - Het + -N(Ra)-N=C(Rb)-Ar,Q -

[0472] (A) (B)

[0473] Het + -N=N-Ar,Q - Ar + -N=N-Ar",Q -

[0474] (C) (D)

[0475] In formulas (A) to (D):

[0476] -Het + represents a cationic heteroaryl such as imidazolium, indolium or pyridinium which preferably carries an intra-ring cationic charge and which is optionally preferably substituted by at least one (C1-C8) alkyl such as methyl;

[0477] -Ar + represents an aryl which preferably carries an extra-ring cationic charge, preferably ammonium, especially tri(C1-C8)alkylammonium such as trimethylammonium, such as phenyl or naphthyl;

[0478] -Ar represents an aryl, especially phenyl, which is optionally preferably substituted by one or more electron-donating groups such as optionally substituted (C1-C8) alkyl, optionally substituted (C1-C8) alkoxy, (di)(C1-C8)(alkyl)amino optionally substituted by hydroxy on the alkyl, aryl(C1-C8)alkylamino and optionally substituted N-(C1-C8)alkyl-N-aryl(C1-C8)alkylamino, or alternatively, Ar represents a julolidine group;

[0479] "-Ar" represents an optionally substituted (hetero)aryl group, such as phenyl or pyrazolyl, which is optionally preferably substituted by one or more (C1-C8) alkyl groups, hydroxy groups, (di)(C1-C8)(alkyl)amino groups, (C1-C8) alkoxy groups or phenyl groups;

[0480] -Ra and Rb may be the same or different and represent a hydrogen atom or a (C1-C8) alkyl group optionally preferably substituted by a hydroxy group;

[0481] Or alternatively, the substituent Ra and the substituent of Het + and / or the substituent Rb and the substituent of Ar together with the atoms carrying them form a (hetero)cycloalkyl group; In particular, Ra and Rb represent a hydrogen atom or a (C1-C4) alkyl group optionally substituted by a hydroxy group;

[0482] -Q - represents an organic or inorganic anionic counterion, such as a halide ion or an alkyl sulfate.

[0483] In particular, mention may be made of azo and hydrazo direct dyes carrying an intra-ring cationic charge of the formula (A) to (D) as previously defined, and more particularly of cationic direct dyes carrying an intra-ring cationic charge as described in patent applications WO 95 / 15144, WO 95 / 01772 and EP 714 954, preferably direct dyes of the following formula (E) and (F):

[0484]

[0485] In formula (E) and (F):

[0486] -R 1 represents a (C1-C4) alkyl group such as methyl;

[0487] -R 2 and R 3 may be the same or different and represent a hydrogen atom or a (C1-C4) alkyl group, such as methyl;

[0488] -R 4 represents a hydrogen atom or an electron-donating group, such as an optionally substituted (C1-C8) alkyl group, an optionally substituted (C1-C8) alkoxy group, or a (di)(C1-C8)(alkyl)amino group optionally substituted by a hydroxy group on the alkyl group; In particular, R 4 is a hydrogen atom;

[0489] -Z represents a CH group or a nitrogen atom, preferably CH;

[0490] -Q - is an anionic counterion as previously defined, particularly a halide ion such as chloride or an alkyl sulfate such as methyl sulfate or mesyl.

[0491] In particular, the dyes of formula (E) and (F) are selected from Basic Red 51, Basic Yellow 87 and Basic Orange 31 or derivatives thereof, where Q - is an anionic counterion as previously defined, in particular a halide ion such as chloride or an alkyl sulfate such as methyl sulfate or mesyl. The direct dyes may be selected from anionic direct dyes. The anionic direct dyes of the present invention are dyes which are generally referred to as "acidic" direct dyes due to their affinity for basic substances.

[0492] The term "anionic direct dye" means any direct dye which contains at least one CO2R' or SO3R' substituent in its structure, where R' denotes a hydrogen atom or a cation derived from a metal or an amine, or an ammonium ion.

[0493] The anionic direct dyes may be selected from direct nitro-acidic dyes, azo-acidic dyes, azine-acidic dyes, triarylmethane-acidic dyes, indoamine-acidic dyes, anthraquinone-acidic dyes, indigoid dyes and natural acidic dyes.

[0494] Among the natural direct dyes which can be used according to the invention, mention may be made of lawsone, juglone, alizarin, purpurin, carminic acid, kermesic acid, gallic acid, protocatechaldehyde, indigo, indigo carmine, curcumin, penicillic acid, apigenidin and orchil. Extracts or decoctions containing these natural dyes may also be used and in particular poultices or extracts based on henna.

[0495] Preferably, the direct dyes are selected from anionic direct dyes.

[0496] The colorant, preferably the pigment, may be present in a concentration ranging from 0.01% to 30% by weight, preferably from 0.2% to 20% by weight and more particularly from 0.5% to 10% by weight, relative to the total weight of the composition containing it.

[0497] The direct dye may be present in a concentration ranging from 0.001% to 10% by weight, preferably from 0.005% to 5% by weight relative to the total weight of the composition containing it.

[0498] Preferably, the cosmetic active agent, in particular the colorant and more particularly the pigment, is introduced into compositions C1, C2, C3, C4 or C5.

[0499] Care active agent

[0500] According to one embodiment of the present invention, in the method of the present invention, the composition C1, C2, C3, C4 or C5 contains one or more care active agents, preferably in an amount of at least 0.01% by weight relative to the total weight of the composition under consideration. In particular, the care active agent can be at least one hydrophilic active agent and / or one lipophilic active agent, and preferably a hydrophilic care active agent.

[0501] The term "hydrophilic active agent" means a water-soluble or water-dispersible active agent capable of forming hydrogen bonds.

[0502] Cosmetic active agents for caring for keratin fibers, especially hair, can be selected in particular from: a1) vitamins and their derivatives; b1) humectants; c1) antioxidant compounds; and mixtures thereof.

[0503] The care active agent can be present in the composition containing it, in particular, in a weight range of from 0.01% to 30% by weight, and preferably from 0.02% to 25% by weight, relative to the weight of the composition.

[0504] Advantageously, the method for treating keratin fibers is a cosmetic method, especially for hair, in particular for caring for, styling and / or coloring keratin fibers, and preferably hair.

[0505] iv) Fatty phase - fatty substance

[0506] According to a specific embodiment, the method of the present invention uses one or more fatty substances, especially one or more oils, preferably volatile oils.

[0507] More particularly, in the method of the present invention, at least one of the compositions C1, C2, C3, C4 or C5 used in the method of the present invention contains a fatty phase.

[0508] In particular, at least one of the compositions C1, C2, C3, C4 or C5 used in the method of the present invention contains one or more fatty substances, especially one or more oils, preferably volatile oils.

[0509] The term "oil" refers to a fatty substance that is liquid at room temperature (20 °C) and atmospheric pressure (760 mmHg).

[0510] The term "hydrocarbon oil" means an oil mainly formed or even composed of carbon and hydrogen atoms and possibly oxygen and nitrogen atoms and not containing any silicon or fluorine atoms. The hydrocarbon oil can contain alcohol, ester, ether, carboxylic acid, amine and / or amide groups.

[0511] According to one embodiment of the present invention, the oil is selected from volatile oils, especially:

[0512] *Hydrocarbon oils containing 8 to 16 carbon atoms, and in particular:

[0513] - Branched C8-C 16 alkanes, alone or as a mixture, such as isoparaffins (also known as isoparaffins), such as C 13 -C 16 isoparaffins, isododecane, isodecane, isocetane, and oils sold, for example, under the trade names Isopar or Permetyl, preferably isododecane (also known as 2,2,4,4,6-pentamethylheptane), more preferably isododecane;

[0514] - Straight-chain alkanes, alone or as a mixture, such as C 11 -C 16 alkanes, such as hexane, decane, undecane, tridecane, or n-dodecane (C12) and n-tetradecane (C14), undecane-tridecane mixtures, mixtures of n-undecane (C11) and n-tridecane (C13), and mixtures thereof, and also mixtures of n-undecane (C11) and n-tridecane (C13);

[0515] - Volatile, non-aromatic cyclic C5-C 12 alkanes;

[0516] * Short-chain esters containing a total of 3 to 8 carbon atoms, such as ethyl acetate, methyl acetate, propyl acetate, or n-butyl acetate;

[0517] * Carbonate hydrocarbon oils of the structure R’1-O-C(O)-O-R’2, where R’1 and R’2 independently denote straight-chain, branched-chain, or cyclic C4-C8 alkyl groups, preferably C4-C8 alkyl groups, and the carbonate hydrocarbon oils are advantageously selected from dibutyl carbonate or dipentyl carbonate;

[0518] * Ether oils of the formula R1-O-R2, where R1 and R2 independently denote straight-chain, branched-chain, or cyclic C4-C8 alkyl groups, preferably C4-C8 alkyl groups;

[0519] * Silicon oils containing particularly 2 to 7 silicon atoms, which optionally contain alkyl or alkoxy groups containing 1 to 10 carbon atoms, such as polydimethylsiloxanes with viscosities of 5 and 6 cSt, cyclopentasiloxane, dodecamethylpentasiloxane, cyclohexasiloxane, octamethylcyclotetrasiloxane, decamethylcyclopentasiloxane, dodecamethylcyclohexasiloxane, heptamethylhexyltrisiloxane, heptamethyloctyltrisiloxane, hexamethyldisiloxane, octamethyltrisiloxane, decamethyltetrasiloxane, dodecamethylpentasiloxane, and mixtures thereof;

[0520] More preferably, the volatile oil b) is selected from C8-C 16 alkanes, especially branched alkanes such as isododecane.

[0521] In particular, at least one of the compositions C1, C2, C3, C4 or C5 used in the method according to the invention comprises one or more non-volatile oils, which are especially selected from:

[0522] * Non-volatile fluorinated oils, which are especially selected from fluorinated polyethers and also fluorosilicone oils, fluorosilicones;

[0523] * Non-volatile silicone oils, which are especially selected from non-volatile polysiloxanes having the following INCI names: dimethicone, dimethiconol, trimethylpentaphenyltrisiloxane, tetramethyltetraphenyltrisiloxane, diphenylpolydimethylsiloxane, trimethylsilyloxy phenyl polydimethylsiloxane, phenylpolymethylsiloxane, diphenylsilyloxy phenyl polymethylsiloxane; and also mixtures thereof;

[0524] * Non-volatile non-polar hydrocarbon-based oils, which are especially selected from the following straight-chain or branched-chain compounds of mineral or synthetic origin: i) liquid paraffin, ii) squalane, isoeicosane, iii) straight-chain saturated hydrocarbons, more particularly C 15 -C 28 mixtures of hydrocarbons, such as those having the INCI name (C 15 -C 19 ) alkane, (C 18 -C 21 ) alkane, (C 21 -C 28 ) alkane mixtures, iv) hydrogenated or non-hydrogenated polybutene; v) hydrogenated or non-hydrogenated, preferably hydrogenated polyisobutene, vi) hydrogenated or non-hydrogenated polydecene, vii) decene / butene copolymers, butene / isobutene copolymers and viii) mixtures thereof;

[0525] * Non-volatile polar hydrocarbon-based oils, which may be selected from:

[0526] i) saturated, unsaturated, straight-chain or branched-chain C 10 -C 26 fatty alcohols, preferably monohydric alcohols; advantageously, said C 10 -C 26 alcohols are preferably branched-chain fatty alcohols when they contain at least 16 carbon atoms; preferably, said fatty alcohols contain from 10 to 24 carbon atoms and more preferably from 12 to 22 carbon atoms, especially lauryl alcohol, isostearyl alcohol, oleyl alcohol, 2-butyl octanol, 2-undecyl pentadecanol, 2-hexyl decanol, isocetyl alcohol, octyldodecanol and mixtures thereof;

[0527] ii) triglycerides consisting of fatty acid esters of glycerol, especially the fatty acids thereof may have a range of C4 to C 36 and especially C 18from C 36 chain lengths, and these oils may be straight-chain or branched-chain, saturated or unsaturated; by way of example, mention may be made in particular of triglycerides of heptanoic or octanoic acid, triglycerides of octanoic / decanoic acid, vegetable oils such as wheat germ oil, sunflower oil, grape seed oil, sesame seed oil, corn oil, almond oil, castor oil, shea butter, avocado oil, olive oil, soybean oil, sweet almond oil, palm oil, rapeseed oil, cottonseed oil, hazelnut oil, macadamia nut oil, jojoba oil, alfalfa oil, poppy oil, pumpkin oil, zucchini oil, blackcurrant oil, evening primrose oil, millet oil, barley oil, quinoa oil, rye oil, safflower oil, candlenut oil, passionflower oil, musk rose oil, peanut oil, coconut oil, argan oil, passionflower oil, torreya grandis oil; the liquid part of shea butter and the liquid part of cocoa butter; and also mixtures thereof;

[0528] iii) straight-chain aliphatic hydrocarbon esters of the formula R-C(O)-OR', where R-C(O)-O- represents a carboxylic acid residue containing from 2 to 40 carbon atoms and R' represents a hydrocarbon chain containing from 1 to 40 carbon atoms, aliphatic hydrocarbon esters of alkylene diols, especially ethylene glycol or propylene glycol; the total number of carbon atoms is advantageously at least 10; said straight-chain aliphatic hydrocarbon esters are especially selected from isopentyl laurate, cetearyl octanoate, isopropyl myristate, isopropyl palmitate, isopropyl stearate or isopropyl isostearate, ethyl palmitate, 2-ethylhexyl palmitate, isostearyl isostearate, octyl stearate, isostearyl heptanoate, octanoates, decanoates or ricinoleates of alcohols or polyols, such as propylene glycol dioctanoate, cetyl alcohol octanoate or tridecyl alcohol octanoate, 2-ethylhexyl palmitate, alkyl benzoates, polyethylene glycol diheptanoate, propylene glycol bis(2-ethylhexanoate) and mixtures thereof, hexyl laurate, neopentanoates, such as isodecyl neopentanoate, isotridecyl neopentanoate, isostearyl neopentanoate or 2-octyldodecyl neopentanoate, isononanoates, such as isononyl isononanoate, isotridecyl isononanoate or isooctyl isononanoate, oleyl erucate, isopropyl lauroylsarcosinate, diisopropyl sebacate, isocetyl stearate, isodecyl neopentanoate, isostearyl behenate or myristyl myristate;

[0529] iv) hydroxylated esters, such as polyglyceryl-2 triisostearate;

[0530] v) aromatic esters, such as tridecyl trimellitate, benzoates C 12 -C 15 alcohol esters, 2-phenylethyl benzoate and butyl octyl salicylate;

[0531] vi) straight-chain fatty acid esters having a total carbon number in the range from 35 to 70, for example pentaerythritol tetranonanoate;

[0532] vii)C 24 -C 28Esters of branched fatty acids or fatty alcohols, such as triisoarachidyl citrate, pentaerythritol tetraisononanoate, glyceryl triisostearate, glyceryl tris(2-decyltetradecanoate), pentaerythritol tetraisostearate, polyglyceryl-2 tetraisostearate or pentaerythritol tetra(2-decyltetradecanoate);

[0533] viii) Polyesters obtained by the condensation of dimers and / or trimers of unsaturated fatty acids and diols, such as those having the INCI name of dicaplinoleic acid / butylene glycol copolymer or dicaplinoleic acid / propylene glycol copolymer; polyesters obtained by the condensation of fatty acid dimers and diol dimers, such as dimeric dilinoleyl dilinoleate;

[0534] ix) Synthetic ethers containing from 10 to 40 carbon atoms, such as dioctyl ether;

[0535] x) Dialkyl carbonates, where the two alkyl chains may be the same or different, such as dicapryl carbonate;

[0536] xi) Vinylpyrrolidone copolymers such as vinylpyrrolidone / 1-hexadecene copolymer; and

[0537] xii) Mixtures thereof;

[0538] * The non-volatile carbonate oils may be selected from carbonates of the formula R8-O-C(O)-O-R9, where R8 and R9 may be the same or different and represent straight-chain or branched C4 to C 12 and preferably C6 to C 10 alkyl chains; the carbonate oils may be dicapryl carbonate (or dicaprylyl carbonate), bis(2-ethylhexyl) carbonate, dipropylheptyl carbonate, dibutyl carbonate, dipivalyl carbonate, dipentyl carbonate, dineopentylheptyl carbonate, diheptyl carbonate, diisononyl carbonate or dinonyl carbonate and preferably dicapryl carbonate;

[0539] * Oils of the formula R1-O-R2 called non-volatile ether oils, where R1 and R2 independently denote straight-chain, branched-chain or cyclic C6-C 24 alkyl, preferably C6-C 18 alkyl, and preferably C8-C 12Alkyl. R1 and R2 can preferably be the same. Straight-chain alkyls that can be mentioned include hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, eicosyl, behenyl, docosyl, tricosyl, and tetracosyl. Branched-chain alkyls that can be mentioned include 1,1-dimethylpropyl, 3-methylhexyl, 5-methylhexyl, ethylhexyl, 2-ethylhexyl, 5-methyloctyl, 1-ethylhexyl, 1-butylpentyl, 2-butyloctyl, isotridecyl, 2-pentylnonyl, 2-hexyldecyl, isostearyl, 2-heptylundecyl, 2-octyldodecyl, 1,3-dimethylbutyl, 1-(1-methylethyl)-2-methylpropyl, 1,1,3,3-tetramethylbutyl, 3,5,5-trimethylhexyl, 1-(2-methylpropyl)-3-methylbutyl, 3,7-dimethyloctyl, and 2-(1,3,3-trimethylbutyl)-5,7,7-trimethyl octyl. As cyclic alkyls, cyclohexyl, 3-methylcyclohexyl, and 3,3,5-trimethylcyclohexyl can be mentioned, dilauryl ether, diisostearyl ether, dioctyl ether, nonylphenyl ether, dodecyldimethylbutyl ether, cetyl dimethylbutyl ether, cetyl isobutyl ether, and mixtures thereof;

[0540] More preferably, c) the non-volatile oil is selected from hydrogenated or non-hydrogenated, preferably hydrogenated polyisobutene, such as series of non-volatile compounds; C 15 -C 19 a mixture of alkanes, and a straight-chain aliphatic hydrocarbon group ester of the formula R-C(O)-OR', where R-C(O)-O represents a carboxylic acid residue containing 2 to 40 carbon atoms, and R' represents a hydrocarbon group chain containing 1 to 40 carbon atoms, as previously defined, especially isononyl isononanoate.

[0541] Very preferably, the method of the present invention uses one or more hydrocarbon group oils containing 8 to 16 carbon atoms, either alone or as a mixture, and especially branched-chain C8-C 16 alkanes, such as isoparaffins such as C 13 -C 16 isoparaffins, isododecane, isodecane, isocetane, preferably isododecane.

[0542] In particular, the amount of oil in at least one of the compositions C1, C2, C3, C4, or C5 used in the method according to the present invention is 1% to 99% by weight, more particularly 10% to 90% by weight, preferably 25% to 75% by weight, still better 30% to 70% by weight, relative to the total weight of the composition.

[0543] Composition :

[0544] According to one embodiment, the methods for treating keratin fibers and the compositions C1 to C5 used in the method of the present invention contain water.

[0545] According to an advantageous variant, C1 is aqueous or water-alcoholic.

[0546] According to an advantageous variant, C2 is aqueous or water-alcoholic.

[0547] According to an advantageous variant, C3 is aqueous or water-alcoholic.

[0548] According to an advantageous variant, C4 is aqueous or water-alcoholic.

[0549] According to an advantageous variant, C5 is aqueous or water-alcoholic.

[0550] According to another specific embodiment of the present invention, C1 is an anhydrous composition. According to another variant, C2 is anhydrous. According to another variant, C3 is anhydrous. According to yet another variant, C4 is anhydrous. According to another variant, C5 is anhydrous. In particular, C1 and / or C4 are anhydrous. In particular, C4 is anhydrous and it contains at least one oil, especially a volatile oil such as isododecane.

[0551] The compositions C1 to C5 used in the method of the present invention may also contain one or more organic solvents.

[0552] The term "organic solvent" means an organic substance capable of dissolving another substance without chemically changing it.

[0553] Examples of organic solvents that may be mentioned include: a) C2-C6 alkanols such as ethanol and isopropanol; b) polyols miscible with water at room temperature (25 °C), said polyols being especially selected from polyols especially containing 2 to 10 carbon atoms, preferably containing 2 to 6 carbon atoms, such as glycerol, propylene glycol, 1,3-propanediol, butanediol, pentanediol, hexanediol, dipropylene glycol, diethylene glycol, or diglycerol; c) polyol ethers such as 2-butoxyethanol, propylene glycol monomethyl ether, diethylene glycol monoethyl ether or diethylene glycol monomethyl ether; and also d) aromatic alcohols such as benzyl alcohol or phenoxyethanol, and mixtures thereof.

[0554] According to a specific embodiment, the composition further contains one or more polyols, especially selected from polyols especially containing 2 to 10 carbon atoms, preferably containing 2 to 6 carbon atoms, such as glycerol.

[0555] In particular, composition C1, C2, C3, C4 or C5 (preferably C2 or C3) is aqueous or water-alcoholic (ethanol / water mixture, in particular with a volume ratio of 1 / 99 to 99 / 1, more particularly 10 / 90 to 90 / 10, even more particularly 20 / 80 to 80 / 20, preferably 40 / 60 to 60 / 40 such as 50 / 50).

[0556] Compositions C1, C2, C3, C4 or C5 may be in the form of an anhydrous water-in-oil emulsion or an oil-in-water emulsion.

[0557] Auxiliary agent

[0558] The compositions C1, C2, C3, C4 or C5 used in the process of the present invention may also contain one or more auxiliary agents selected from the following: perfumes, preservatives, fillers, radical scavengers, polymers, thickeners or film formers, surfactants, trace elements, softeners, chelating agents and propellants.

[0559] Another subject of the present invention is a composition C1, which is preferably aqueous or water-alcoholic, and which comprises i) at least one compound of formula (I) or (Ia) and iii) optionally at least one active agent as defined previously, preferably at least one dye, such as at least one pigment as defined previously; and optionally iv) one or more fatty substances as defined previously.

[0560] Another subject of the present invention is a composition C2, which is preferably aqueous or water-alcoholic, and which comprises i) at least one compound of formula (I) or (Ia) as defined previously, ii) at least one crosslinking agent as defined previously and iii) optionally at least one active agent as defined previously; and optionally iv) one or more fatty substances as defined previously.

[0561] Another subject of the present invention is a composition C3, which is preferably aqueous or water-alcoholic, and which comprises i) at least one compound of formula (I) or (Ia) as defined previously, ii) at least one crosslinking agent as defined previously and iii) at least one active agent as defined previously; and optionally iv) one or more fatty substances as defined previously.

[0562] Another subject of the present invention is the use of at least one component i) in combination with at least one component ii) and optionally in combination with at least one component iii) and optionally in combination with at least one component iv) for treating keratin fibers, in particular for caring for, styling, shaping (curling) and / or coloring keratin fibers, in particular hair, said components i) to iv) being as defined previously.

[0563] Another subject of the invention is the cosmetic use of composition C3, as defined previously, for treating keratin fibers, in particular for coloring keratin fibers, especially hair.

[0564] Another subject of the invention is the cosmetic use of composition C2, as defined previously, for treating keratin fibers, in particular for styling keratin fibers, preferably hair.

[0565] The following examples illustrate the invention in more detail. The amounts are indicated in percentages by weight.

[0566] Examples

[0567] Compound 1: K-FLEX 7301 sold by King Industrie

[0568] [Chemical formula 5]:

[0569]

[0570] Compound 2: Glucose carrying acetoacetate functional groups (5 equivalents)

[0571] Compound 2 was synthesized according to the following scheme:

[0572] [Chemical formula 6]:

[0573]

[0574] In this scheme, R1 may be the same or different and represents a hydrogen atom or -methylcarbonylmethylcarbonyl-C(O)-CH2-C(O)-CH3, it being understood that at least two groups R1 represent -C(O)-CH2-C(O)-CH3.

[0575] 100 g of D-glucose and 482.90 g of tert-butyl acetoacetate were placed in a 1-liter three-necked flask equipped with a mechanical stirrer and a distillation column. The reaction medium was heated for 5 h using an oil bath (oil bath temperature 150 °C - 160 °C). After 5 h, NMR confirmed the grafting of the acetoacetate functional group. The reaction medium was then concentrated on a rotary evaporator at 150 °C under continuous vacuum. A highly viscous dark brown liquid was obtained, which corresponded to the expected product after analysis.

[0576] Compound 3: Mannose carrying acetoacetate functional groups (5 equivalents)

[0577] Compound 3 was synthesized according to the following scheme:

[0578] [Chemical formula 7]:

[0579]

[0580] In this scheme, R1 can be the same or different and represents a hydrogen atom or a -C(O)-CH2-C(O)-CH3 group. It should be understood that at least two groups R1 represent -C(O)-CH2-C(O)-CH3.

[0581] 100 g of D-mannose and 482.90 g of tert-butyl acetoacetate were placed in a 1 L three-necked flask equipped with a mechanical stirrer and a distillation column. The reaction medium was heated for 5 h using an oil bath (oil bath temperature 140 °C - 150 °C). After 5 h, NMR confirmed the grafting of the acetoacetate functional group. The reaction medium was then concentrated on a rotary evaporator at 150 °C under continuous vacuum. A viscous yellow liquid was obtained, which corresponded to the expected product after analysis.

[0582] Compound 4: Xylitol carrying acetoacetate functional groups (5 equivalents)

[0583] Compound 4 was synthesized according to the following scheme:

[0584] [Chemical formula 8]:

[0585]

[0586] In this scheme, R1 can be the same or different and represents a hydrogen atom or a -C(O)-CH2-C(O)-CH3 group. It should be understood that at least two groups R1 represent -C(O)-CH2-C(O)-CH3.

[0587] 25 g of xylitol and 142.69 g of tert-butyl acetoacetate were placed in a 500 ml three-necked flask equipped with a mechanical stirrer and a distillation column. The reaction medium was heated for 5 h using an oil bath (oil bath temperature 140 °C - 150 °C). After 5 h, NMR confirmed the grafting of the acetoacetate functional group. The reaction medium was then concentrated on a rotary evaporator at 150 °C under continuous vacuum. A highly viscous brown liquid was obtained, which corresponded to the expected product after analysis.

[0588] Compound 5: Sorbitol carrying acetoacetate functional groups (6 equivalents)

[0589] Compound 5 was synthesized according to the following scheme:

[0590] [Chemical formula 9]:

[0591]

[0592] In this scheme, R1 can be the same or different and represents a hydrogen atom or a -C(O)-CH2-C(O)-CH3 group. It should be understood that at least two groups R1 represent -C(O)-CH2-C(O)-.

[0593] Place 100 g of sorbitol and 573.20 g of tert-butyl acetoacetate in a 1-liter three-necked flask equipped with a mechanical stirrer and a distillation column. Heat the reaction medium using an oil bath (oil bath temperature 140 °C - 150 °C) for 5 h. After 5 h, NMR confirmed the grafting of the acetoacetate functional group. Then concentrate the reaction medium on a rotary evaporator at 150 °C under continuous vacuum. A viscous yellow-orange liquid was obtained, which corresponded to the expected product after analysis.

[0594] Compound 6: Sorbitol carrying acetoacetate functional groups (3 equivalents)

[0595] Synthesize compound 6 according to the following scheme:

[0596] [Chemical formula 10]:

[0597]

[0598] In this scheme, R1 can be the same or different and represents a hydrogen atom or a -C(O)-CH2-C(O)-CH3 group. It should be understood that at least two groups of R1 represent -C(O)-CH2-C(O)-CH3.

[0599] Place 100 g of sorbitol and 260.54 g of tert-butyl acetoacetate in a 1-liter three-necked flask equipped with a mechanical stirrer and a distillation column. Heat the reaction medium using an oil bath (oil bath temperature 140 °C - 150 °C) for 5 h. After 5 h, NMR confirmed the grafting of the acetoacetate functional group. Then concentrate the reaction medium on a rotary evaporator at 150 °C under continuous vacuum. A viscous yellow liquid was obtained, which corresponded to the expected product after analysis.

[0600] Compound 7: Dipentaerythritol carrying acetoacetate functional groups (6 equivalents)

[0601] Synthesize compound 7 according to the following scheme:

[0602] [Chemical formula 11]:

[0603]

[0604] In this scheme, R1 can be the same or different and represents a hydrogen atom or a -C(O)-CH2-C(O)-CH3 group. It should be understood that at least two groups of R1 represent -C(O)-CH2-C(O)-CH3.

[0605] 50 g of dipentaerythritol and 195.33 g of tert-butyl acetoacetate were placed in a 1-liter three-necked flask equipped with a mechanical stirrer and a distillation column. The reaction medium was heated for 4 h using an oil bath (oil bath temperature 140 °C - 150 °C). After 4 h, NMR confirmed the grafting of the acetoacetate functional group. Then the reaction medium was concentrated on a rotary evaporator at 150 °C under continuous vacuum. A viscous orange-brown liquid was obtained, which corresponded to the expected product after analysis.

[0606] Compound 8: Pentaerythritol tetraacetoacetate

[0607] Compound 8 was synthesized according to the following scheme:

[0608] [Chemical formula 12]:

[0609]

[0610] 100 g of pentaerythritol and 510.89 g of tert-butyl acetoacetate were placed in a 1-liter three-necked flask equipped with a mechanical stirrer and a distillation column. The reaction medium was heated for 4 h using an oil bath (oil bath temperature 140 °C - 150 °C).

[0611] After 4 h, NMR confirmed the grafting of the acetoacetate functional group. Then the reaction medium was concentrated on a rotary evaporator at 150 °C under continuous vacuum. A clear viscous yellow liquid was obtained, which corresponded to the expected product after analysis.

[0612] Compound 9: Sucrose carrying acetoacetate functional groups (8 equivalents)

[0613] Compound 9 was synthesized according to the following scheme:

[0614] [Chemical formula 13]:

[0615]

[0616] In this scheme, R1 can be the same or different and represents a hydrogen atom or a -C(O)-CH2-C(O)-CH3 group, it should be understood that at least two groups R1 represent -C(O)-CH2-C(O)-CH3.

[0617] 100 g of sucrose and 406.55 g of tert-butyl acetoacetate were placed in a 1-liter three-necked flask equipped with a mechanical stirrer and a distillation column. The reaction medium was heated for 4 h using an oil bath (oil bath temperature 140 °C - 150 °C). After 4 h, NMR confirmed the grafting of the acetoacetate functional group. Then the reaction medium was concentrated on a rotary evaporator at 150 °C under continuous vacuum.

[0618] A viscous yellow-orange liquid was obtained, which corresponded to the expected product after analysis.

[0619]

[0620]

[0621] Embodiments of the present invention

[0622] Single - gesture application:

[0623] Before application to the hair, compounds 1 to 9 carrying an acetoacetate functional group and crosslinkers 1 to 9 are mixed together. The system is kept fluid long enough to allow application to the hair. The new materials produced on the hair enable the formation of transfer - resistant, non - sticky deposits after evaporation of the volatile solvent, which are resistant to at least two shampoo washes and to water, for application to the hair.

[0624] Two - gesture application:

[0625] Base coat A: Deposits of compounds 1 to 9 carrying an acetoacetate functional group, either alone or diluted in a volatile solvent such as ethanol, water, isododecane or a mixture of isododecane / ethanol or ethanol / water. Optionally, a crosslinker can be introduced into this phase for pre - crosslinking.

[0626] Or

[0627] Base coat B: Deposits of crosslinkers 1 to 9, and then

[0628] Top coat A: Deposits with crosslinkers 1 to 9, or

[0629] Top coat B: Deposits of compounds 1 to 9 carrying an acetoacetate functional group, either alone or diluted in a volatile solvent such as ethanol, water, isododecane or a mixture of isododecane / ethanol or ethanol / water.

[0630] Example 1: Compound 1 and amino crosslinking agent 1 (acid catalysis)

[0631] Compositions A and B as described below are prepared from mixtures of different solutions.

[0632] Solution 1, i.e., 3 - aminopropyltriethoxysilane (APTES) solution, is prepared according to the following method: Pure APTES (APTES Silsoft A - 1100 sold by Momentive Performance Materials) is mixed with water adjusted to pH = 1 by adding HCl, and then ethanol is added. Then the mixture is stirred for 24 hours at room temperature using a VWR magnetic stirrer (rotation speed 500 rpm).

[0633] Solution 2, an aqueous-alcoholic solution containing a pigment and a polyol acetoacetate, was prepared according to the following method: The pigment (iron oxide sold by Sun Chemical under the name SunPuro red iron oxide) was dispersed in ethanol. Then, the polyol acetoacetate compound sold by Kinghawk Industry Co., Ltd. under the name K-Flex 7301 was added to the pigment solution.

[0634] Composition A according to the present invention was prepared by mixing Solution 1 and Solution 2. Composition B is a comparative composition without polyol.

[0635] The various compounds were present in the following amounts (expressed in g / 100g).

[0636] [Table 1]

[0637]

[0638] Each of Composition A and Composition B was applied to dry natural hair locks containing 90% white hair strands at a ratio of 1 g of the composition / gram of hair lock. After applying Composition A and Composition B to these hair locks, the hair locks were combed and dried with a hair dryer, and then left to stand in a fume hood at room temperature for 24 hours.

[0639] The hair was dyed evenly and strongly.

[0640] Then, the thus-dyed hair locks were subjected to a test of repeated shampoo washings in order to evaluate the fastness (persistence) of the obtained coloring with respect to shampoo washing according to the shampoo washing protocol described below.

[0641] Shampoo washing protocol: The hair locks of the dyed hair were combed, wetted with water at 35 °C and then passed through five times between the fingers for 5 seconds. Then, the hair locks were squeezed dry between two fingers.

[0642] The standard shampoo (Garnier Ultra Doux) was uniformly applied to the dyed hair locks at a ratio of 0.4 g of the standard shampoo / gram of hair lock, and the hair locks were gently massaged for 15 seconds along the length from the roots to the ends (6 passes).

[0643] Then, the hair locks were placed on a watch glass and left to stand for 1 minute.

[0644] Next, the hair locks were rinsed with water while passing the hair locks through between the fingers (15 passes). Then, the hair locks were squeezed dry between two fingers, and then the next shampoo washing was carried out.

[0645] After carrying out the test of several shampoo washings, the hair locks were combed and dried with a hair dryer.

[0646] Persistence protocol: The persistence of the color of the tresses was evaluated using a Minolta CM3600A spectrophotometer colorimeter (light source D65, 10° angle, including specular reflectance component) in the CIE L*a*b* system.

[0647] In this L*a*b* system, L* represents the intensity of the color, a* represents the green / red axis and b* represents the blue / yellow axis.

[0648] The persistence of the coloring was evaluated by the color difference ΔE between the dyed tresses before washing with shampoo and then after undergoing 1 and 3 or 5 shampoo washings according to the protocol described above. The lower the ΔE value, the more persistent the color with respect to shampoo washing. The ΔE value was calculated according to the following equation:

[0649]

[0650] In this equation, L*a*b* represents the values measured after dyeing the hair and after shampoo washing, and L0*a0*b0* represents the values measured after dyeing the hair but before shampoo washing.

[0651] The chromaticity was calculated according to the following equation:

[0652]

[0653] The evaluation results are summarized in the following table:

[0654] Colorimetric measurements:

[0655] [Table 2]

[0656]

[0657] Tresses dyed with Composition A according to the invention had a significantly lower ΔE value than tresses dyed with Comparative Composition B. It was also seen that the chromaticity of the hair dyed with Composition A according to the invention did not change significantly, while the chromaticity of the hair dyed with Comparative Composition B decreased very significantly after five shampoo washings.

[0658] Example 2: Compound 1 and amino crosslinking agent 1 + PDMS-OH (base catalysis)

[0659] Compositions C and D as described below were prepared from mixtures of different solutions.

[0660] Solution 3, namely a 3-aminopropyltriethoxysilane (APTES) solution, was prepared according to the following method: pure APTES (APTES Silsoft A-1100 sold by Momentive Performance Materials Inc.) was mixed with water adjusted to pH = 1 by adding HCl, and then ethanol was added. Then the mixture was stirred at room temperature for 24 hours using a VWR magnetic stirrer (rotation speed 500 rpm).

[0661] Solution 4, which is an alcoholic solution of a non-amino silicone containing at least two reactive groups, was prepared according to the following method: a polydimethylsiloxane (PDMS) compound carrying a hydroxyl-terminal functional group (481939 sold by Sigma-Aldrich) was diluted in ethanol in which a pigment (iron oxide sold by Sun Chemical under the name SunPuro Red Iron Oxide) was dispersed. Then a polyol acetoacetate compound sold by Kinghawk Industrial Co., Ltd. under the name K-Flex 7301 was added to the pigment solution.

[0662] Composition C according to the present invention was prepared by mixing Solutions 3 and 4. Composition D is a comparative composition.

[0663] The various compounds were present in the following amounts (expressed in g / 100 g).

[0664] [Table 3]

[0665]

[0666]

[0667] Each of Compositions C and D was applied to dry natural hair locks containing 90% white hair strands at a ratio of 1 g of composition / gram of hair lock. After applying Compositions C and D to these hair locks, the hair locks were combed and dried with a hair dryer, and then left to stand in a fume hood at room temperature for 24 hours.

[0668] The hair was dyed evenly and strongly.

[0669] Then the thus-dyed hair locks were subjected to a test of repeated shampoo washings in order to evaluate the fastness (persistence) of the obtained coloring with respect to shampoo washings according to the same protocol as applied in Example 1.

[0670] The evaluation results are summarized in the following table:

[0671] Colorimetric measurement:

[0672] [Table 4]

[0673]

[0674] Strands of hair dyed with Composition A according to the present invention have a significantly lower ΔE value than strands of hair dyed with Composition B. It is also seen that there is no significant change in the chromaticity of hair dyed with Composition C according to the present invention, while the chromaticity of hair dyed with Comparative Composition D decreases very significantly after three shampoo washes or even five shampoo washes.

[0675] Example 3: Compound 1 and amino crosslinking agent 1 + PDMS-OH (acid catalysis)

[0676] Compositions E and F as described below are prepared from a mixture of different solutions.

[0677] Solution 5, i.e., a 3-aminopropyltriethoxysilane (APTES) solution, is prepared according to the following method: pure APTES (APTES Silsoft A-1100 sold by Momentive Performance Materials Inc.) is mixed with water adjusted to pH = 1 by adding HCl, and then ethanol is added. The mixture is then stirred at room temperature for 24 hours using a VWR magnetic stirrer (rotation speed 500 rpm).

[0678] Solution 6, which is an alcoholic solution of a non-amino silicone containing at least two reactive groups, is prepared according to the following method: a polydimethylsiloxane (PDMS) compound carrying a hydroxyl terminal functional group (481939 sold by Sigma-Aldrich) is diluted in ethanol in which a pigment (iron oxide sold by Sun Chemical under the name SunPuro Red Iron Oxide) is dispersed. Then a polyol acetoacetate compound sold by Young-In Chemical Co., Ltd. under the name K-Flex 7301 is added to the pigment solution.

[0679] Composition E according to the present invention is prepared by mixing Solution 5 and Solution 6. Composition F is a comparative composition.

[0680] The various compounds are present in the following amounts (expressed in g / 100 g).

[0681] [Table 5]

[0682]

[0683]

[0684] Each of Compositions E and F is applied to dry natural hair strands containing 90% white hair filaments at a ratio of 1 g of composition / gram of hair strand. After applying Compositions E and F to these hair strands, the hair strands are combed and dried with a hair dryer, and then left to stand in a fume hood at room temperature for 24 hours.

[0685] The hair is dyed evenly and strongly.

[0686] Then the thus - dyed tresses of hair were subjected to a test of repeated shampoo washings a number of times in order to evaluate the fastness (persistence) of the color obtained with respect to shampoo washings according to the same protocol as applied in Example 1.

[0687] The evaluation results are summarized in the following table:

[0688] Colorimetric measurement:

[0689] [Table 6]

[0690]

[0691] The tresses of hair dyed with Composition E according to the invention had a lower ΔE value than the tresses of hair dyed with Composition F.

[0692] Furthermore, it was seen that the chromaticity of the hair colored with Composition E according to the invention did not change significantly, while the chromaticity of the hair dyed with the comparative Composition F decreased very significantly after five shampoo washings.

[0693] Example 4: Compound 4 and amino crosslinking agent 1 (without solvent - single gesture)

[0694] Composition G was prepared from a mixture of different compounds as described below.

[0695] Composition G

[0696] [Table 7]

[0697]

[0698] *a.m.: active material

[0699] Composition G was applied to dry natural tresses of hair containing 90% white hair filaments at a rate of 1 g of composition per gram of tress. After application to the tress, the tress was combed and dried with a hair dryer and then left standing in a fume hood at room temperature for 24 hours.

[0700] The hair was dyed uniformly and strongly.

[0701] Then the thus - dyed tresses of hair were subjected to a test of repeated shampoo washings a number of times in order to evaluate the fastness (persistence) of the color obtained with respect to shampoo washings according to the same protocol as applied in Example 1.

[0702] The evaluation results are summarized in the following table:

[0703] Colorimetric measurements:

[0704] [Table 8]

[0705]

[0706] Tresses of hair dyed with Composition G according to the invention did not show a significant decrease in color even after five shampoo washes. Thus, it can be seen that the method of the invention allows for obtaining a coloration that is persistent with respect to shampoo washes. In addition, the color intensity of Composition G remained strong after five shampoo washes.

[0707] Example 5: Compound 5 and amino crosslinking agent 1 (single gesture)

[0708] Composition H was prepared from a mixture of different compounds as described below.

[0709] Composition H

[0710] [Table 9]

[0711]

[0712] Composition H was applied to dry natural tresses containing 90% white hair strands at a rate of 1 g of composition per gram of tress. After application to the tress, the tress was combed and dried with a hair dryer, and then left to stand for 24 hours in a fume hood at room temperature.

[0713] The hair was dyed evenly and strongly.

[0714] Then, the tresses of hair so dyed were subjected to a test of several repeated shampoo washes in order to evaluate the fastness (persistence) of the coloration obtained with respect to shampoo washes according to the same protocol as applied in Example 1.

[0715] The evaluation results are summarized in the table below:

[0716] Colorimetric measurement:

[0717] [Table 10]

[0718]

[0719] Tresses of hair dyed with Composition H according to the invention did not show a significant decrease in color even after three or even five shampoo washes. Thus, it can be seen that the method of the invention allows for obtaining a coloration that is persistent with respect to shampoo washes. In addition, the color intensity of Composition H remained strong after three or even five shampoo washes.

[0720] Example 6: Compound 5 pre-crosslinked with amino crosslinking agent 2, followed by a second gesture with amino crosslinking agent 3

[0721] Composition I and J were prepared from a mixture of different compounds as described below.

[0722] Composition I

[0723] [Table 11]

[0724]

[0725] Composition J (second gesture)

[0726] [Table 12]

[0727]

[0728] Composition I was applied to dry natural hair locks containing 90% white hair strands at a rate of 0.5 g of composition per gram of hair lock, and then combed. After this first gesture, Composition J was applied to the hair lock at a rate of 0.5 g / g of hair lock. After application, the hair lock was combed and dried with a hair dryer, and then left to stand for 24 hours in a fume hood at room temperature.

[0729] The hair was dyed evenly and strongly. The thus-dyed hair locks were then subjected to a test of repeated shampoo washings in order to evaluate the fastness (persistence) of the coloring obtained with respect to shampoo washing according to the same protocol as that applied in Example 1.

[0730] The hair locks dyed with the composition of Example 6 according to the invention had a very strong hold: L* = 32.65 after 0 shampoo washings, and L* = 34.21 after three shampoo washings.

[0731] Example 7: Compound 5 pre-crosslinked with amino crosslinking agent 2, followed by a second gesture with thiol crosslinking agent 5

[0732] Compositions K and L were prepared from mixtures of different compounds as described below.

[0733] Composition K

[0734] [Table 13]

[0735]

[0736] Composition L (Second gesture)

[0737] [Table 14]

[0738]

[0739] Composition K was applied to dry natural hair locks containing 90% white hair strands at a rate of 0.5 g of composition per gram of hair lock, and then combed. After this first gesture, Composition L was applied to the hair lock at a rate of 0.5 g / g of hair lock. After application, the hair lock was combed and dried with a hair dryer, and then left to stand for 24 hours in a fume hood at room temperature.

[0740] The hair was dyed evenly and strongly.

[0741] Then the thus - dyed tresses are subjected to a test of repeated shampoo washings several times in order to evaluate the fastness (persistence) of the coloring obtained with respect to shampoo washings according to the same protocol as that applied in Example 1.

[0742] After application of the composition of Example 7, the color obtained was found to be strong (L* = 33.91) and chromatic (C* = 25.36).

[0743] Example 8: Styling application: Styling evaluation protocol

[0744] The styling evaluation protocol is detailed as follows:

[0745] A 2 - g solution containing the described formulation is sprayed onto tresses (90% natural white (NW) hair, 20.5 cm in length). The tresses are weighed before and after application. Approximately 0.5 g of the polymer - containing solution is effectively deposited on the tresses.

[0746] One - g tresses of keratin fibers (90% natural white NW hair, 20.5 cm in length) are wound around a brush (approximately 2 cm in diameter over a length of 3 cm). The tresses are left standing at room temperature (at 25 °C).

[0747] After 24 hours, the tresses are released from the brush and suspended. Then the length of the tresses is measured. After 24 hours of suspension, the length of the tresses is measured again.

[0748] It is compared with tresses onto which only the reference formulation is sprayed.

[0749] Formulations 1, 2, 3, 5, 6, 8, 9, 11, and 12 are comparative “reference” formulations. Formulations 4, 7, 10, and 13 are formulations according to the invention.

[0750] Compositions of the various formulations described below are prepared from mixtures of different compounds.

[0751] Formulation No. 1

[0752] [Table 15]

[0753]

[0754] [Table 16]

[0755]

[0756]

[0757] L0 = length after application to the initial tresses Li = length after application to tress i The evaluation results are summarized in the table below:

[0758] [Table 17]

[0759]

[0760]

[0761] [Table 18]

[0762]

[0763] It can be seen that the tresses treated with formulations 4, 7, 10, and 13 according to the present invention show a significant improvement in the shape of the curls, which appear more shaped and tighter, as opposed to the control tresses. Additionally, even after 24 hours, the tresses lose significantly less of their curly shape compared to the control tresses.

[0764] Example 9: Compound 7 pre-crosslinked with amino crosslinking agent 1, followed by a second gesture with amino crosslinking agent 8

[0765] Compositions A1 and B1 as described below are prepared from a mixture of different compounds.

[0766] Composition A1

[0767] [Table 19]

[0768]

[0769] Composition B1 (second gesture)

[0770] [Table 20]

[0771]

[0772] Composition A1 is applied to dry natural hair tresses containing 90% white hair strands at a rate of 0.5 g of composition per gram of tress, and then combed. After this first gesture, composition B1 is applied to the tress at a rate of 0.5 g / g of tress.

[0773] After application, the tresses are combed and dried with a hair dryer, and then left to stand for 24 hours in a fume hood at room temperature.

[0774] The hair is evenly and strongly dyed.

[0775] Then the thus-dyed hair tresses are subjected to a test of repeated shampoo washings in order to evaluate the fastness (persistence) of the obtained coloring with respect to shampoo washings according to the same protocol as applied in Example 1.

[0776] The evaluation results are summarized in the table below:

[0777] Colorimetric measurements:

[0778] [Table 21]

[0779]

[0780] The dyed tresses showed good color persistence after three shampoo washes.

[0781] Example 10: Compound 8 pre-crosslinked with amino crosslinking agent 9, followed by a second gesture with thiol crosslinking agent 5

[0782] Compositions C1 and D1 as described below are prepared from a mixture of different compounds.

[0783] Composition C1

[0784] [Table 22]

[0785]

[0786]

[0787] Composition D1 (second gesture)

[0788] [Table 23]

[0789]

[0790] Composition C1 is applied to dry natural hair tresses containing 90% white hair strands at a rate of 0.5 g of composition per gram of tress, and then combed. After this first gesture, composition D1 is applied to the tress at a rate of 0.5 g / g of tress.

[0791] After application, the tresses are combed and dried with a hair dryer, and then left to stand for 24 hours at room temperature in a fume hood.

[0792] The hair is evenly and strongly dyed.

[0793] The thus-dyed hair tresses are then subjected to several repeated shampoo wash tests in order to evaluate the fastness (persistence) of the obtained coloration with respect to shampoo washes according to the same protocol as applied in Example 1.

[0794] The evaluation results are summarized in the table below:

[0795] Colorimetric measurement:

[0796] [Table 24]

[0797]

[0798] The dyed tresses showed good color persistence after three shampoo washes.

[0799] Example 11: Compound 9 pre-crosslinked with amino crosslinking agent 3, followed by a second gesture with thiol crosslinking agent 5

[0800] Compositions E1 and F1 as described below are prepared from a mixture of different compounds.

[0801] Composition E1

[0802] [Table 25]

[0803]

[0804] Composition F1 (second gesture)

[0805] [Table 26]

[0806]

[0807] Composition E1 is applied to dry natural hair locks containing 90% white hair strands at a rate of 0.5 g of composition per gram of hair lock, and then combed. After this first gesture, composition F1 is applied to the hair lock at a rate of 0.5 g / g of hair lock.

[0808] After application, the hair locks are combed and dried with a hair dryer, and then left to stand in a fume hood at room temperature for 24 hours.

[0809] The hair is dyed evenly and strongly.

[0810] Then the thus-dyed hair locks are subjected to a test of repeated shampoo washings in order to evaluate the fastness (persistence) of the obtained coloring with respect to shampoo washings according to the same protocol as applied in Example 1.

[0811] The evaluation results are summarized in the table below:

[0812] Colorimetric measurement:

[0813] [Table 27]

[0814]

[0815] The dyed hair locks showed good color persistence after three shampoo washings.

[0816] Example 12: Hair dyeing with the step of applying a steam straightening iron

[0817] Preparations G1, G1a, G1b, H1, H1a, H1b as described below are prepared from a mixture of different compounds.

[0818] The content is expressed as the weight percentage of the active material relative to the total weight of the composition.

[0819] [Table 28]

[0820]

[0821] The formulations G1, G1a, G1b, H1, H1a, and H1b were applied to dry natural hair tresses containing 90% white hair strands at a rate of 1 g of composition per gram of hair tress.

[0822] The hair tresses were then combed and dried with a hair dryer for 1 minute and 30 seconds, and then a steam straightener (Rowenta Steampod) was applied to the hair tresses five times at a temperature of 210 °C.

[0823] The hair tresses were then subjected to a test of repeated shampoo washings in order to evaluate the fastness (persistence) of the color obtained relative to shampoo washing according to the same protocol as applied in Example 1.

[0824] The evaluation results are summarized in the table below:

[0825] [Table 29]

[0826]

[0827] Hair tresses dyed with compositions G1 and H1 according to the method of the present invention have lower ΔE values than hair tresses dyed with comparative compositions G1a - G1b and H1a - H1b.

[0828] Thus, the method according to the present invention provides a uniform color coating on the hair, which shows improved resistance to shampoo washing.

[0829] Example 13: Hair dyeing

[0830] Compositions I1 to Q1 were prepared from mixtures of different compounds as described below.

[0831] The contents are expressed as weight percentages of the active material relative to the total weight of the composition.

[0832] [Table 30]

[0833]

[0834]

[0835] [Table 31]

[0836]

[0837]

[0838] Single gesture application:

[0839] Compositions I1 to L1 and P1 to Q1 were applied to dry natural hair tresses containing 90% white hair strands at a ratio of 1 g of composition per gram of tress, then combed and dried with a hair dryer, and then left to stand for 24 hours at room temperature under a fume hood.

[0840] The hair was dyed evenly and strongly.

[0841] The thus-dyed hair tresses were then subjected to a test of repeated shampoo washings in order to evaluate the fastness (persistence) of the obtained coloring with respect to shampoo washings according to the same protocol applied in Example 1.

[0842] Two - gesture application:

[0843] The first composition solution 1 (10% APTES in water at pH 10) was applied to dry natural hair tresses containing 90% white hair strands at a ratio of 0.6 g of composition per gram of tress.

[0844] The hair tresses were combed and then left to stand for 5 minutes. The tresses were then gently rinsed with water and then dried with a hair dryer for 1 minute 30 seconds.

[0845] After this first gesture, the second composition M1, N1 or O1 was applied to the hair tresses at a ratio of 1 g of composition per gram of tress, and then the tresses were combed and dried with a hair dryer and then left to stand for 24 hours at room temperature under a fume hood.

[0846] The hair was dyed evenly and strongly.

[0847] The thus-dyed hair tresses were then subjected to a test of repeated shampoo washings in order to evaluate the fastness (persistence) of the obtained coloring with respect to shampoo washings according to the same protocol applied in Example 1.

[0848] The evaluation results are summarized in the following table:

[0849] Colorimetric measurements:

[0850] [Table 32]

[0851]

[0852] The hair tresses dyed with compositions I1 to Q1 showed good coloring persistence after 15 shampoo washings.

[0853] Example 14

[0854] Single gesture application:

[0855] Compositions A2 and B2 were prepared from mixtures of different compounds as described below.

[0856] The content is expressed as a weight percentage of the active material relative to the total weight of the composition.

[0857] [Table 33]

[0858]

[0859] Compositions A2 and B2 were applied to dry natural hair locks containing 90% white hair strands at a rate of 1 g of composition / gram of hair lock, and then combed. After application, the hair locks were combed and dried with a hair dryer, and then left standing in a fume hood at room temperature for 24 hours.

[0860] The hair was dyed evenly and strongly. Then, the thus-dyed hair locks were subjected to several repeated shampoo wash tests in order to evaluate the fastness (persistence) of the obtained coloring relative to shampoo washing according to the same protocol as applied in Example 1.

[0861] The evaluation results are summarized in the following table:

[0862] Colorimetric measurement:

[0863] [Table 34]

[0864]

[0865] The hair locks dyed with Composition A2 according to the present invention have a lower ΔE value than the hair locks dyed with Comparative Composition B2.

[0866] Therefore, compared with the method using the comparative composition, the method according to the present invention provides a coloring coating showing improved shampoo wash resistance.

[0867] Two - gesture application:

[0868] The following Compositions A3, B3, and C3 were prepared from mixtures of different compounds as described below.

[0869] The content is expressed as a weight percentage of the active material relative to the total weight of the composition.

[0870] Compositions A3 and B3

[0871] [Table 35]

[0872]

[0873] Composition C3 (second gesture)

[0874] [Table 36]

[0875]

[0876] Composition A3 or B3 was applied to dry natural hair locks containing 90% white hair strands at a rate of 0.5 g of composition per gram of hair lock, and then combing was carried out. After this first gesture, composition C3 was applied to the hair lock at a rate of 0.5 g / g of hair lock. After application, the hair lock was combed and dried with a hair dryer, and then left to stand for 24 hours in a fume hood at room temperature.

[0877] The hair was dyed evenly and strongly. Then the thus-dyed hair locks were subjected to a test of repeated shampoo washings in order to evaluate the fastness (persistence) of the obtained coloring with respect to shampoo washings according to the same protocol as that applied in Example 1.

[0878] The evaluation results are summarized in the following table:

[0879] Colorimetric measurement:

[0880]

[0881] The hair locks dyed with composition A3 and then composition C3 according to the method of the present invention have a lower ΔE value than the hair locks dyed with comparative composition B3 and then composition C3.

[0882] Thus, with respect to the method using the comparative composition, the method according to the present invention provides a coloring coating showing improved shampoo wash resistance.

Claims

1. A method for treating keratin fibers in one or more steps by applying to said fibers the following: i) one or more compounds of formula (I) and also their optical or geometric isomers, their salts and their solvates such as hydrates: In formula (I): -R 1 represents a linear or branched, saturated or unsaturated, conjugated or non-conjugated, acyclic or cyclic, aromatic or non-aromatic C2 to C 14 polyvalent hydrocarbon radical group, R 1 Also: a) optionally substituted by one or more hydroxyl OH or dialkylamino - N(R)2 groups, where R represents (C1 - C4) alkyl, carboxyl - C(O) - OH, vinyl, and / or b) Optionally inserted with one or more heteroatoms or groups selected from O, S, carbonyl-C(O)-, amine-N(R’), or a combination thereof, where R' represents a hydrogen atom, a straight-chain or branched-chain alkyl group having 1 to 4 carbon atoms, which is optionally substituted with at least one hydroxyl group (OH), or optionally substituted with -X-C(O)-C(R a )(R b )-C(O)-R 2 substituted; -R 2 represents a linear or branched, saturated or unsaturated C1-C6 monovalent hydrocarbon radical group; -R a and R b may be the same or different and represent a hydrogen atom or a (C1-C4) alkyl group; - X is a heteroatom or group selected from: O, S, N(R’) or - S - CH2 - C(O) - O -, - O - C(O) - CH2 - S -, - O - C(O) - N(R’)-, - N(R’)-C(O) - O - or - N(R’)-C(O) - N(R’)-; - n indicates an integer ranging from 2 to 10, particularly from 3 to 8; and ii) at least one cross - linker; and iii) optionally at least one cosmetic active agent.

2. The method according to the preceding claim, wherein, The compounds of formula (I) are selected from those of formula (Ia) and also their optical or geometric isomers, their salts and their solvates such as hydrates: In formula (Ia): -R 1 is as defined in claim 1 and in particular represents a linear or branched, saturated or unsaturated, conjugated or non-conjugated, acyclic or cyclic, aromatic or non-aromatic C2 to C 14 , preferably C3 to C 12 and preferably C4 to C 10 polyvalent hydrocarbon radical, R 1 Further: a) optionally substituted by one or more hydroxyl OH, and / or b) optionally inserted with one or more heteroatoms or groups selected from O, S, - N(R’), preferably inserted with one or more oxygen atoms, where R’ is as defined in the previous claim; -R 2 is as defined in claim 1, and preferably R 2 represents a straight-chain or branched (C1-C6) alkyl group, preferably a (C1-C4) alkyl group, more preferably methyl or tert-butyl, such as methyl; and - n is as defined in claim 1, and preferably n indicates an integer ranging from 2 to 8.

3. The method according to any one of the preceding claims, wherein, The compound of formula (I) or (Ia) is such that: R 1 represents a straight-chain or branched-chain, unsaturated monocyclic or bicyclic, preferably monocyclic C6-C8 polyvalent hydrocarbon radical group and an aromatic group such as phenyl, or R 1 represents a saturated monocyclic or bicyclic C5 to C 12 polyvalent hydrocarbon radical which is optionally interrupted by one or more heteroatoms or groups selected from O, S, -N(R'), where R' represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, preferably interrupted by one or more oxygen atoms; preferably, R 1 represents a monosaccharide or polysaccharide unit, in particular a disaccharide, in which n hydroxyl groups have been replaced by n groups -O-C(O)-CH2-C(O)-R 2 where R 2 and n are as defined in any one of the preceding claims, or R 1 represents a straight-chain or branched-chain, saturated or unsaturated, preferably saturated, acyclic C2 to C 12 and preferably C3-C 10 polyvalent hydrocarbon radical group.

4. The method according to any one of the preceding claims, wherein, The compound of formula (I) or (Ia) is such that: n indicates an integer ranging from 2 to 8, and more particularly n indicates an integer ranging from 3 to 6, more particularly 3 to 5.

5. The method according to any one of the preceding claims, wherein, The compound of formula (I) or (Ia) is selected from the following compounds and also their optical isomers, their salts and their solvates such as hydrates: where R1 may be the same or different and represents a hydrogen atom or a - C(O) - CH2 - C(O) - CH3 group, it being understood that at least two groups R1 represent - C(O) - CH2 - C(O) - CH3, preferably at least three groups R1 represent - C(O) - CH2 - C(O) - CH3; More preferably, the compound is selected from (16), (18), (21), (35), (36), (37), (38), (39), (40) and (46), and still better from (16), (21), (35), (38), (39) and (46); Even more preferably, the compound is selected from (16), (18), (21), (35), (36), (37), (38), (39) and (40), and still better from (16), (21), (35), (38) and (39); Advantageously, the compound is selected from (18), (21), (36), (37), (38), (39) and (40), and still better from (21), (38) and (39).

6. The method according to any one of the preceding claims, wherein, The crosslinking agent ii) is selected from: (Poly)amines, (poly)thiols, (poly)carbonyls, (poly)acrylates and / or metal alkoxide compounds, and mixtures thereof; preferably, the crosslinking agent is selected from (poly)amines, (poly)thiols and (poly)acrylate compounds, and mixtures thereof.

7. The method according to any one of the preceding claims, wherein, The crosslinking agent is selected from: -(Poly)amine compounds selected from the following: a) chitosan, such as poly(D-glucosamine), b) polyether diamines, especially polyethylene glycol α,ω-diamines (carrying amine functional groups at the chain ends) and 4,7,10-trioxa-1,1-tridecane diamine, c) polyether triamines, such as polyetheramines (or Jeffamines), d) aminoalkoxysilanes, such as APTES, e) polydialkylsiloxanes containing primary amine groups at the chain ends or on the side chains, especially polydimethylsiloxanes containing primary amine groups, such as bis(3-aminopropyl)-terminated poly(dimethoxysiloxane) (PDMS-diNH2) and amino-terminated polydimethylsiloxanes containing amine groups on the side chains, such as bis(cetylstearylamino)-terminated polydimethylsiloxane, f) polyamine alkanes, such as those of formula (XII’) H2N-Alk-NH2, where Alk is a (C1-C6) alkylene group optionally substituted with one or more amino groups and / or optionally interrupted with one or more -N(H)-, such as spermidine; and -(Poly)thiol compounds selected from the following: a) polydialkylsiloxanes carrying thiol functional groups, and b) alkoxysilanes carrying thiol functional groups, and particularly (poly)thiol compounds selected from a) polydialkylsiloxanes carrying thiol functional groups, preferably polydimethylsiloxanes containing thiol groups (such as mercaptopropyl) on the side chains, especially those of formula (XIII) R a -Si(R b )(R d )-O-[Si(R a )(R b )-O] m -[Si(R b )(ALK1-SH)-O] n -Si(R b )(R d )-R a (XIII) In the said formula (XIII): ·R a and R b may be the same or different, preferably the same, and represents a group selected from: (C1-C4) alkyl such as methyl, (C1-C4) alkoxy such as methoxy, aryl such as phenyl, aryloxy such as phenoxy, aryl(C1-C4) alkyl such as benzyl, or aryl(C1-C4) alkoxy such as benzyloxy, preferably (C1-C4) alkyl such as methyl; and R d is as defined for R a and R b ; preferably, R a , R b and R d are the same and represent methyl, ·R d It may also represent a (C1-C6) alkyl group, preferably a (C1-C4) alkyl group such as methyl, substituted by a (C1-C4) alkylamino or amino or thiol group; ·ALK1 represents a straight-chain or branched, optionally cyclic, saturated or unsaturated divalent hydrocarbon chain containing 1 to 100 carbon atoms, optionally interrupted with one or more heteroatoms such as oxygen, sulfur or nitrogen (especially O), (thio)carbonyl C(X) — where X represents O or S, or a combination thereof, such as -O-, -O-C(O)- or -C(O)-O-; preferably, ALK1 represents a (C1-C6) alkylene group, and more preferably a (C1-C4) alkylene group such as propylene; · n and m can be the same or different and represent integers greater than 2, and more particularly the values of m and n are such that the weight average molecular weight of said polyorganosiloxane is from 1000 to 55000 g.mol -1 ; -(Meth)acrylate L of formula (XIV) [-Y-C(O)-C(R e )=CH2] q (XIV) In the said formula (XIV): ·q represents an integer greater than or equal to 2; ·L indicates a saturated or unsaturated straight-chain or branched, or saturated or unsaturated (hetero)cyclic polyvalent (at least divalent) group, which particularly contains 1 to 500 carbon and / or silicon atoms, more particularly 2 to 40 carbon and / or silicon atoms, even more particularly 3 to 30 carbon and / or silicon atoms, preferably 6 to 20 carbon atoms; L is optionally inserted with and / or terminated with the following items: one or more heteroatoms or groups selected from O, S, N, Si, and C(X) and combinations thereof, such as -O-, -O-C(X)-, -N(R)-C(X)-, or -Si(R c )(R d )-O-, where R represents a hydrogen atom or a (C1-C6) alkyl group such as methyl; and / or L is optionally substituted with one or more groups selected from the following: -N(R a )R b and -(X’) a -C(X)-(X”) b -R a ; wherein X, X' and X'' may be the same or different and represent an oxygen or sulfur atom, or a group N(R b )); a and b are equal to 0 or 1; preferably, the sum of a + b is equal to 1; R a and R b may be the same or different and represent a hydrogen atom or a (C1-C6) alkyl or aryl(C1-C4) alkyl such as benzyl, preferably R a and R b represents a hydrogen atom; and R c and R d may be the same or different and represent a (C1-C6) alkyl, an aryl(C1-C4) alkyl or a (C1-C6) alkoxy group. ·R e represents a hydrogen atom or a (C1-C4) alkyl group such as a methyl group; preferably, R e represents a hydrogen atom; and · Y represents an oxygen atom or an amino - N(H)-, preferably O as previously defined, preferably Y = O and R e = H, preferably L represents a divalent or trivalent, preferably trivalent hydrocarbon chain containing 1 to 8 carbon atoms, q is 2 or 3, preferably 3, Y represents O, and R e represents a hydrogen atom; Preferably, the compound of formula (XIV) is trimethylolpropane triacrylate. -Metal alkoxides selected from those of formula (XIVa), such as titanium butoxide M-(OR1) n (XIV a ) In the formula (XIV a ): · M represents an atom selected from the following: alkaline earth metals, transition metals, lanthanide metals, post-transition metals such as aluminum or tin, and metalloids such as boron; preferably transition metals such as Ti and post-transition metals such as aluminum; · n represents the valence of the atom represented by M; · R1 represents a straight-chain or branched, saturated or unsaturated hydrocarbon group containing 1 to 30 carbon atoms, preferably 1 to 6 carbon atoms, and the hydrocarbon group is optionally inserted with 1 to 20 heteroatoms selected from O, N, S, and P, especially O or N; and / or the hydrocarbon group is optionally substituted by one or more hydroxyl or carbonyl groups; Preferably, M represents an atom selected from the following: transition metals such as titanium or zirconium or alkaline earth metals such as magnesium, more preferably an atom selected from the following: transition metals such as titanium or zirconium, and even more preferably titanium.

8. The method according to any one of the preceding claims, the method using iii) one or more cosmetic active agents, the cosmetic active agents being especially selected from a) colorants such as pigments, direct dyes and mixtures thereof, b) active agents for caring for keratin fibers, preferably hair, c) UV screening agents, and d) mixtures thereof; preferably, the at least one cosmetic reagent is selected from colorants, preferably selected from pigments, direct dyes and mixtures thereof, more preferably pigments; more preferably selected from carbon black, iron oxides, especially yellow, red and black iron oxides, and mica coated with iron oxide, triarylmethane pigments, especially blue and purple triarylmethane pigments such as Lake Blue 1, azo pigments, especially red azo pigments such as D&C Red 7, the alkali metal salt of Lithol Red such as the calcium salt of Lithol Red B, SunPuro Red Iron Oxide, and even more preferably red iron oxide, yellow iron oxide and azo pigments, especially red azo pigments such as SunPuro Red Iron Oxide.

9. The method according to any one of the preceding claims, the method using iv) one or more fatty substances, especially one or more oils, preferably volatile oils.

10. The method according to any one of the preceding claims, the method using iv) one or more volatile oils selected from the following: * Hydrocarbon oils containing 8 to 16 carbon atoms, and especially: - Branched C8-C, either alone or as a mixture 16 alkanes, such as isoparaffins like C 13 - C 16 isoparaffins, isododecane, isodecane, and isohexadecane, preferably isododecane, more preferably isododecane; - Linear alkanes, either alone or as a mixture, such as C 11 - C 16 alkanes, such as hexane, decane, undecane, tridecane, or n-dodecane (C12) and n-tetradecane (C14), undecane-tridecane mixtures, mixtures of n-undecane (C11) and n-tridecane (C13), and mixtures thereof, as well as mixtures of n-undecane (C11) and n-tridecane (C13); - Volatile, non-aromatic cyclic C5-C 12 alkanes; * Short-chain esters containing a total of 3 to 8 carbon atoms, such as ethyl acetate, methyl acetate, propyl acetate or n-butyl acetate; * Carbonate hydrocarbon oils of the structure R’1-O-C(O)-O-R’2, where R’1 and R’2 independently denote a straight-chain, branched or cyclic C4-C8 alkyl group, preferably a C4-C8 alkyl group, and the carbonate hydrocarbon oils are advantageously selected from dibutyl carbonate or dipentyl carbonate; * Ether oils of the formula R1-O-R2, where R1 and R2 independently denote a straight-chain, branched or cyclic C4-C8 alkyl group, preferably a C4-C8 alkyl group; Silicone oils containing specifically from 2 to 7 silicon atoms, which optionally contain alkyl or alkoxy groups having from 1 to 10 carbon atoms, such as polydimethylsiloxanes with viscosities of 5 and 6 cSt, cyclopentasiloxane, dodecamethylpentasiloxane, cyclohexasiloxane, octamethylcyclotetrasiloxane, decamethylcyclopentasiloxane, dodecamethylcyclohexasiloxane, heptamethylhexyltrisiloxane, heptamethyloctyltrisiloxane, hexamethyldisiloxane, octamethyltrisiloxane, decamethyltetrasiloxane, dodecamethylpentasiloxane, and mixtures thereof; More preferably, the volatile oil iv) is selected from C8-C 16 alkanes, especially branched alkanes such as isododecane.

11. The method according to any one of the preceding claims, said method being particularly for the care, styling and / or dyeing of keratin fibers and preferably hair, said method using: - a composition designated "C1", said composition comprising i) at least one compound of formula (I) or (Ia) as defined in any one of claims 1 to 5, and optionally iii) at least one cosmetic active agent as defined in any one of claims 1 and 8; - a composition designated "C2", said composition comprising i) at least one compound of formula (I) or (Ia) as defined in any one of claims 1 to 5, and ii) at least one crosslinking agent as defined in any one of claims 1, 6 or 7, and optionally iii) at least one active agent as defined in any one of claims 1 and 8; - a composition designated "C3", said composition comprising i) at least one compound of formula (I) or (Ia) as defined in any one of claims 1 to 5, ii) at least one crosslinking agent as defined in any one of claims 1, 6 or 7, and iii) at least one cosmetic active agent as defined in any one of claims 1 and 8; and / or - composition "C4", said composition comprising ii) at least one crosslinking agent as defined in any one of claims 1, 6 or 7, and optionally iii) at least one cosmetic active agent as defined in any one of claims 1 and 8; - composition "C5", said composition comprising iii) at least one cosmetic active agent as defined in any one of claims 1 and 8; it being understood that: · the method uses i) at least one compound of formula (I) or (Ia) as defined in any one of claims 1 to 5 and ii) at least one crosslinking agent as defined in any one of claims 1, 6 or 7, either together or separately; · compositions C1, C2, C3, C4 and C5 can be anhydrous, aqueous or water-alcoholic and / or can contain one or more fatty substances iv) as defined in claims 9 or 10.

12. The method according to the preceding claim, said method being carried out in one gesture by applying composition C2 or C3 to the keratin fibers.

13. The method according to claim 11, wherein the method is carried out by two gestures by continuously applying two different compositions C1 and C4, or C2 and C4, or C3 and C4 to the keratin fibers, preferably C1 then C4, C2 then C4, or C3 then C4, preferably C2 or C3 and then C4.

14. The method according to claim 11 or 13, wherein the method is a method for dyeing keratin fibers, in particular hair, and the method at least comprises sequentially applying: - composition C2 as defined in claim 11; - composition C4 as defined in claim 11; and - composition C5 as defined in claim 11; It should be understood that composition C2 and / or C4 and / or C5 contains at least one dye as defined in claim 8, preferably at least one pigment; preferably, composition C5 contains at least one pigment.

15. Use of at least one ingredient i) as defined in any one of claims 1 to 10 in combination with at least one ingredient ii) and optionally in combination with at least one ingredient iii) and optionally in combination with at least one ingredient iv) for treating keratin fibers, in particular for caring for, styling, maintaining shape (curl) and / or coloring keratin fibers, in particular hair.

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