A process for coloring keratin fibers comprising the application of at least one particular acetoacetate compound, a chitosan compound and a coloring agent.

Abstract

The present invention relates to a method for coloring keratin fibers comprising applying the following ingredients to said keratin fibers, in one or more separate compositions: i) at least one chitosan compound; ii) at least one acetoacetate compound of formula (I); iii) at least one coloring agent selected from pigments, direct dyes, and mixtures thereof. The invention also relates to a composition comprising at least one specific chitosan compound and at least one beneficial agent selected from coloring agents, acetoacetate compounds, and mixtures thereof.

Description

Title of the invention: A method for coloring keratin fibers comprising the application of at least one particular acetoacetate compound, a chitosan compound and a coloring agent.

[0001] The present invention relates to a method for coloring keratin fibers comprising the application to said keratin fibers of at least one particular chitosan compound, at least one compound with specific acetoacetate functions and at least one coloring agent, said ingredients being included in one or more separate compositions.

[0002] The invention also relates to a composition comprising at least one particular chitosan compound, and at least one beneficial agent selected from coloring agents, acetoacetate compounds, and mixtures thereof.

[0003] Cosmetic products for the temporary coloring of keratin fibers can conventionally employ one or more film-forming polymers to achieve a high-quality deposit of these products onto the keratin fibers, and in particular, to meet the expectations detailed below. This deposit should be as natural as possible, notably by forming a continuous, non-flaking deposit, without dulling or opacifying the color, and ideally by providing greater shine to the treated keratin fibers.

[0004] Furthermore, in the hair care sector, a new range of products known as hair makeup, or "Hair Make-up," has recently been developed. These products guarantee temporary hair coloring that lasts after one to three shampoos. They constitute a particularly attractive alternative for consumers to permanent hair coloring, provided, of course, that the color effect is effectively maintained upon contact with water and a few shampoos. This requirement is also met, in particular, through the use of effective film-forming agents. Thus, for example, document FR 2 741 530 proposes, for this purpose, for the temporary coloring of keratin fibers, the use of a dispersion of film-forming polymer particles comprising at least one acid functional group and at least one pigment dispersed in the continuous phase of said dispersion.The colors obtained using this coloring method are not always satisfactory in terms of permanence, particularly after shampooing. In fact, generally speaking, these polymers do not allow for the deposition on keratin fibers that meets all the aforementioned requirements, namely very good water resistance, especially to hair shampoos, which allows for adjustments. qualities of shine or invisibility and which, in the case of hair use, provide a very satisfactory hold of the hairstyle.

[0005] US document 2006 / 0079599 describes a medical polymer-based tissue adhesive in which certain ACAC (acetoacetate) group polymers are associated with polyamines in the form of a hydrogel.

[0006] Document EP 3 250 177 A1 describes the use of acetoacetylated compounds in the field of keratin fibers. Keratin fibers treated with said acetoacetylated compounds do not always give satisfactory results, particularly in terms of resistance to water and shampoos.

[0007] There therefore remains a need to make available processes for coloring keratin fibers which allow for intense, chromatic or natural colorings, and which exhibit good color development, as well as good resistance to water and shampoos, in order to guarantee color retention over time, particularly in terms of intensity and / or chromaticity.

[0008] There also remains a need to make available processes for coloring keratin fibers having good resistance to friction, with color transfer to textiles as limited as possible, both dry and wet.

[0009] There also remains a need for a process of coloring keratin fibers which, apart from the color, is as invisible as possible, which at a minimum does not dull the treated fibers and better, gives them shine.

[0010] Furthermore, the formulation of environmentally friendly cosmetic products, that is to say, whose design and development take into account environmental issues, is becoming a major concern in order to help meet global challenges.

[0011] It is therefore essential to propose more sustainable compositions and / or preparation processes and / or ingredients, thus enabling us to meet these environmental challenges.

[0012] In this context, it is important to develop processes for preparing cosmetic products and / or cosmetic ingredients with a better carbon footprint capable of reducing the generation of carbon dioxide throughout the product life and / or low cost in energy and water and / or using greener solvents and / or with fewer synthesis steps and / or with good atom economy.

[0013] The present invention is specifically designed to meet all or part of these needs.

[0014] The present invention relates in particular to a method for coloring fibers keratinous comprising the application to said keratinous fibers of the following ingredients, which are included in one or more separate compositions: i) at least one chitosan compound comprising at least 2 repeating units, different from each other, of the following general formula (A): in which:

[0015] - RI independently represents a hydrogen atom or a group -(CH2CH(R')Y)qX in which:

[0016] - X denotes a hydrogen atom or a -SO3, M+ radical or an N+(R' i)3 radical, Year - q denotes an integer ranging from 1 to 20,

[0017] - Y designates an oxygen atom or a divalent methylene radical -CH2-; - R' independently represents a hydrogen atom, a methyl group, or a hydroxyl group. - R'i independently represents an alkyl group in Ci-C4, - An represents a mineral or organic anion, preferably with a single charge, such as a halide (preferably chloride, bromide), sulfate, sulfonate, carboxylate (preferably acetate, lactate, citrate);

[0018] - M+ represents a mineral or organic cation, preferably with a single charge, such as a alkali metal cation such as sodium or potassium; - R2 represents a hydrogen atom, a -C(O)R”'- group, or a group chosen from -CH2CH(R')-CH2-SO3, M+ or -CH2CH(R')-CH2-N+(R'i)3, An in which R' is as defined previously and - R”' represents a Ci-C30 hydrocarbon radical, saturated or unsaturated, linear or branched, possibly substituted by at least one hydroxyl group, it being understood that:

[0019] - at least one of the RI radicals is different from a hydrogen atom; and

[0020] - at least one of the radicals RI designates a hydrogen atom; and

[0021] - at least one of the radicals R2 designates a hydrogen atom; and

[0022] - at least one of the radicals R2 is different from a hydrogen atom and different from - CO-CH3; An and M+ being chosen to ensure the electroneutrality of the compounds of formula (A);

[0023] ii) at least one compound of the following formula (I): (I)

[0024] in which: - Z represents a multivalent hydrocarbon radical in C2 to C40, in particular in C3 to C36, linear or branched, saturated or unsaturated, conjugated or not, acyclic or cyclic, aromatic or not, Z possibly being interrupted by one or more heteroatoms or groups chosen from -O-, -N(Ra)-, -S-, -C(O)-, (hetero)cycle(s) and / or their combinations; - AK1 represents a linear or branched divalent hydrocarbon chain saturated or unsaturated in C1-C12, preferably in Ci-C6, more preferably saturated in Ci-C6; - AK2 represents a linear or branched monovalent hydrocarbon chain, saturated or unsaturated, in CrC4o, possibly substituted by one or more identical or different radicals chosen from -OR, -X-AK3-(OC(O)-C(Ra)(Rb)-C(O)-R4)v; and / or said chain being possibly interrupted by one or more heteroatoms or groups chosen from -O-, -S-, -C(O)-, (hetero)cycle(s), and their combinations, in particular -O-(CO)-, -(CO)-O-, -(hetero)cycle-O-(hetero)cycle-; - AK3 represents a linear or branched divalent hydrocarbon chain saturated or unsaturated in C1-C12, preferably in CrC6, more preferentially saturated in Ci-C6, even more preferentially in CrC4; - R represents a hydrogen atom, a linear or branched alkyl radical saturated or unsaturated in Ci-C6, preferably in CrC4, in particular methyl, or a -C(O)-C(Ra)(Rb)-C(O)-R4 radical; - X represents -O-, -S-, -OC(O)- or -C(O)-O-; - Y represents -OC(O)- or -C(O)-O-; -R4 represents a monovalent hydrocarbon radical in C1 to C6, linear or branched, saturated or unsaturated, preferably an alkyl (CrC4) group, in particular methyl or tert-butyl, more preferably methyl; - Ra and Rb, whether identical or different, represent a hydrogen atom or a (Ci-C4)alkyl group, preferably a hydrogen atom; - p denotes an integer equal to 0 or 1; - m denotes an integer equal to 0, 1, 2, 3 or 4; it being understood that when m is greater than 1, then the radicals -Y-AK2 are identical or different; - n denotes an integer equal to 0, 1, 2, 3 or 4; it being understood that when n is greater than 1, then the radicals -(O)t-(AKi)q-(OC(O)-C(Ra)(Rb)-C(O)-R4)u are identical or different; -1 denotes an integer equal to 0 or 1; - q denotes an integer equal to 0 or 1; - u denotes an integer equal to 1, 2 or 3; - v denotes an integer equal to 1, 2 or 3; it being understood that if q is equal to 0 then t is equal to 0, that (m + n) is greater than or equal to 1, and that the compounds of formula (I) contain at least two -C(O)-C(Ra)(Rb)-C(O)-R4 groups; and

[0025] iii) at least one coloring agent selected from pigments, direct colorants, and mixtures thereof.

[0026] It has been observed that the process according to the invention makes it possible to obtain an intense, chromatic or natural colouring of the keratinous fibres and with a good colour rise.

[0027] It has also been observed that the colouring obtained by the process according to the invention is particularly resistant to water and shampoos.

[0028] It has also been found that the colouring obtained by the process according to the invention is resistant to dry and wet rubbing.

[0029] It has also been found that the coloring obtained by the process according to the invention is resistant to transfer to textiles.

[0030] The invention also relates to a composition comprising: - at least one chitosan compound i), - at least one beneficial agent chosen from among a) coloring agents, b) compounds of formula (I) as described below, c) and mixtures thereof.

[0031] Another object of the invention is a device with several distinct compartments comprising: - a first compartment containing i) at least one chitosan compound and optionally iii) at least one coloring agent and / or optionally iv) at least one additional (poly)amine compound, and - a second compartment, separate from the first, containing ii) at least one compound of formula (I) and optionally iii) at least one coloring agent - and possibly a third compartment containing iv) at least one additional (poly)amine compound, and possibly iii) at least one coloring agent, it being understood that at least one of the compartments contains iii) at least one coloring agent.

[0032] Other objects, features, aspects and advantages of the invention will become even clearer upon reading the description and example that follows.

[0033] For the purposes of the present invention, and unless otherwise indicated: - - the expression "at least one" is equivalent to the expression "one or more" and can be substituted for it. - the expression "between... and..." is equivalent to the expression "ranging from... to..." and can be substituted for it, and implies that the limits are included. - By the expression "greater than" and respectively the expression "less than" in the meaning of the present invention, we mean an open interval that is strictly greater than, respectively strictly less than, and therefore that the bounds are not included. - For the purposes of this application, "keratin fibers" refers particularly to human keratin fibers such as hair, eyelashes, eyebrows, and body hair, preferably hair, eyebrows and eyelashes, and even more preferably hair. - For the purposes of this invention, "hair" means the hair on the head. This term does not include body hair, eyebrows, or eyelashes.

[0034] - By "residual color with shampoos" is meant in the sense of the present invention that the colour obtained persists after at least one shampoo, particularly after at least 3 shampoos, preferably at least 5 shampoos.

[0035] - an "aryl" radical represents a mono- or polycyclic hydrocarbon group, condensed or not, comprising from 6 to 14 carbon atoms, and of which at least one ring is aromatic; preferably the aryl radical is a phenyl, biphenyl, naphthyl, indenyl, anthracenyl, or tetrahydronaphthyl;

[0036] - a "heteroaryl" radical represents a mono- or polycyclic group, condensed or not, comprising 5 to 14 links, 1 to 6 heteroatoms chosen from nitrogen, oxygen, sulfur and selenium atoms, and of which at least one ring is aromatic; preferably a heteroaryl radical is chosen from acridinyl, benzimidazolyl, benzobistriazolyl, benzopyrazolyl, benzopyridazinyl, benzoquinolyl, benzothiazolyl, benzotriazolyl, benzoxazolyl, pyridinyl, tetrazolyl, dihydrothiazolyl, imidazopyridinyl, imidazolyl, indolyl, isoquinolyl, naphthoimidazolyl, naphthooxazolyl, naphthopyrazolyl, oxadiazolyl, oxazolyl, oxazolopyridyl, phenazinyl, phenooxazolyl, pyrazinyl, pyrazolyl, pyrilyl, pyrazoyltriazyl, pyridyl, pyridinoimidazolyl, pyrrolyl, quinolyl, tetrazolyl, thiadiazolyl, thiazolyl, thiazolopyridinyl, thiazoylimidazolyl, thiopyrylyl, triazolyl, xanthylyl;

[0037] - By "(hetero)aryl" we mean the aryl or heteroaryl groups;

[0038] - By "(hetero)cycloalkyl" we mean cycloalkyl or heterocycloalkyl groups;

[0039] - The "aryl" or "heteroaryl" radicals or the aryl or heteroaryl part of a radicals can be substituted by at least one substituent attached to a carbon atom, chosen from: • an alkyl radical in Ci-C6, preferably in C1-C4; • a halogen atom such as chlorine, fluorine or bromine; • a hydroxy group; • a C1-C2 alkoxy radical; a C2-C4 (poly)-hydroxyalkoxy radical; • an amino radical; • an amino radical substituted by one or two alkyl radicals, identical or different, in Ci-C6, Ci-C6, preferably in CrC4; • an acylamino radical (-N(R)-C(O)-R') in which the radical R is a hydrogen atom, • an alkyl radical in Ci-C4 and the radical R' is an alkyl radical in Ci-C4; a carbamoyl radical (R2N-C(O)-) in which the R radicals, identical or not, represent a hydrogen atom, an alkyl radical in CrC4; • an alkylsulfonylamino radical (R'S(O)2-N(R)-) in which the radical R represents a hydrogen atom, an alkyl radical in CrC4 and the radical R' represents an alkyl radical in Ci-C4, a phenyl radical; • an aminosulfonyl radical (R2N-S(O)2-) in which the R radicals, identical or not, represent a hydrogen atom, an alkyl radical in Ci-C4; • a carboxylic radical in acidic or salified form (preferably with an alkali metal or an ammonium, substituted or unsubstituted); • a cyano group (CN); • a polyhalogeno(Ci-C4)alkyl group, preferably trifluoromethyl (CF3);

[0040] - the cyclic or heterocyclic part of a non-aromatic radical can be substituted by at least one substituent attached to a carbon atom chosen from the following groups: • hydroxy, • CrC4 alkoxy, C2-C4 (poly)hydroxyalkoxy, • alkylcarbonylamino (RC(O)-NR'-) in which the radical R' is a hydrogen atom, an alkyl radical in CrC4 and the radical R is an alkyl radical in CrC4, amino substituted by one or two identical or different alkyl groups in CrC4; • alkylcarbonyloxy (RC(O)-O-) in which the radical R is a C1-C4 alkyl radical, amino substituted by one or two identical or different C1-C4 alkyl groups; • alkoxycarbonyl (RO-C(O)-) in which the radical R is an alkyl radical in CrC4,;

[0041] - a cyclic radical, heterocyclic radical, or a non-aromatic part of an aryl radical or heteroaryl, can also be substituted by one or more oxo groups;

[0042] - a hydrocarbon chain is unsaturated when it comprises one or more double bonds and / or one or more triple bonds; preferably one or more double bonds;

[0043] - a "cyclic" or "cycloalkyl" radical is a non-cyclic hydrocarbon radical aromatic, mono or polycyclic, condensed or non-condensed, containing from 5 to 14 carbon atoms, which may have from 1 to several unsaturations, preferably the cycloalkyl is a cyclohexyl group;

[0044] - a "heterocyclic" or "heterocycloalkyl" radical is a non-cyclic radical aromatic mono or polycyclic, condensed or non-condensed, containing 3 to 9 links, comprising 1 to 4 heteroatoms chosen from nitrogen, oxygen, sulfur and selenium atoms, preferably the heterocycloalkyl is chosen from epoxide, piperazinyl, piperidinyl, morpholinyl, or dithiolane;

[0045] - an "alkyl" radical is a saturated hydrocarbon radical, linear or branched, in particularly in C1-C6, preferably in C1-C4;

[0046] - an "alkoxy" radical is an alkyl-oxy radical for which the alkyl radical is a hydrocarbon radical, linear or branched, in Ci-C6 preferably in Ci-C4;

[0047] - a "(poly)(hydroxy)alkyl" radical designates a Ci-C6 alkyl radical, of preferably in C1-C4 possibly substituted by one or more hydroxy radicals, preferably substituted by 1 to 4 hydroxy groups, more particularly between 1 and 3;

[0048] - a "sugar" radical is a monosaccharide or disaccharide radical. Examples include: as sugar radical: sucrose (or saccharose), glucose, galactose, ribose, fucose, maltose, fructose, mannose, arabinose, xylose, or lactose;

[0049] - by "monosaccharide" is meant a monosaccharide sugar comprising at least 5 carbon atoms of formula CX(H2O)X, with x an integer greater than or equal to 5, preferably x is greater than or equal to 6, in particular x is inclusively between 5 and 7, preferably x = 6, they may be of D or L configuration, and of alpha or beta anomer, as well as their salts and their solvates such as hydrates;

[0050] - by "disaccharide" we mean a di-osidic sugar which is a compound made up of two sugars linked together by O-glycosidic bonds, said compounds being composed of two monosaccharides (also called mono-glycosidics) such as defined previously the said monosaccharide units comprising at least 5 carbon atoms, preferably 6, particularly the monosaccharide units are linked together in 1,4 or 1,6 in anomer a (alpha) or [3 (beta), each sugar unit being able to be of L or D configuration, as well as its salts and solvates such as the hydrates of said monosaccharides; these are more particularly polymers formed of two sugars (or monosaccharides) having the general formula: -[Cx(H2O)y)] 2- or -[(CH2O)X]2-, with x an integer greater than or equal to 5, preferably x is greater than or equal to 6, in particular x is inclusively between 5 and 7, preferably x = 6, and y an integer which represents x - 1;

[0051] - by “polysaccharide” we mean a polysaccharide sugar which is a polymer consisting of at least 3 sugars linked together by O-glycosidic bonds, said polymers being made up of monosaccharide units (also called mono-glycosidic units) as defined above, said monosaccharide units comprising at least 5 carbon atoms, preferably 6, particularly the monosaccharide units are linked together in 1,4 or 1,6 in anomer a (alpha) or [3 (beta), each glycosidic unit being able to be of L or D configuration, as well as its salts and solvates such as the hydrates of said monosaccharides;more specifically, these are polymers formed from a certain number of sugars (or monosaccharides) having the general formula: -[Cx(H2O)y)]w- or -[(CH2O)X]W-, with x an integer greater than or equal to 5, preferably x greater than or equal to 6, in particular x is between 5 and 7 inclusive, preferably x = 6, and y an integer representing x - 1, and w is an integer greater than or equal to 2, particularly between 3 and 3000 inclusive, more particularly between 5 and 2500, preferably between 10 and 2300, particularly between 15 and 1000 inclusive, more particularly between 20 and 500, preferably between 25 and 200; ;

[0052] - by "organic or mineral acid salt", more particularly means a) the addition salts with a particular organic or mineral acid selected from a salt derived from i) hydrochloric acid HCl, ii) hydrobromic acid HBr, iii) sulfuric acid H2SO4, iv) alkylsulfonic acids: Alk-S(O)2OH such as methylsulfonic acid and ethylsulfonic acid; v) arylsulfonic acids: Ar-S(O)2OH such as benzenesulfonic acid and toluenesulfonic acid; vi) alkoxysulfinic acids: Alk-OS(O)OH such as methoxysulfinic acid and ethoxysulfinic acid; vii) aryloxysulfinic acids such as tolueneoxysulfinic acid and phenoxysulfinic acid; viii) phosphoric acid H3PO4; ix) triflic acid CF3SO3H and x) tetrafluoroboric acid HBF4; xi) organic carboxylic acids R°-C(O)-OH (l'z) formula (Fz) in which R° represents a (hetero)aryl group such as phenyl, (hetero)aryl(Ci-C4)alkyl such that benzyl, or (Ci-Cio)alkyl, said alkyl group being optionally substituted preferably by one or more hydroxy groups, amino radicals, or carboxy groups, R° preferably designating a (Ci-C6)alkyl group optionally substituted by 1, 2 or 3 hydroxy groups, or more preferably monocarboxylic acids of formula (l'z) are chosen from acetic acid, glycolic acid, lactic acid, and mixtures thereof, and more particularly from acetic acid and lactic acid; and polycarboxylic acids are chosen from tartaric acid, succinic acid, fumaric acid, citric acid and mixtures thereof; and xii) amino acids having more carboxylic acid radicals than amino groups such as gamma-carboxyglutamic acid, aspartic acid, glutamic acid, in particular gamma-carboxyglutamic acid;or b) addition salts with an organic or mineral base such as hydroxides of alkali metals, alkaline earth metals, carbonates of alkali metals or alkaline earth metals, bicarbonates of alkali metals or alkaline earth metals, addition salts with so-called basic amino acids such as arginine, lysine, addition salts with amines possibly hydroxylated;

[0053] - an "anionic counterion" is an anion or an associated anionic group to the cationic charge; more particularly the anionic counter-ion is chosen from i) halides such as chloride, bromide; ii) nitrates; iii) sulfonates including the Ci-C6 alkylsulfonates: Alk-S(O)2O such as methylsulfonate or mesylate and ethylsulfonate; iv) arylsulfonates: Ar-S(O)2O such as benzenesulfonate and toluenesulfonate or tosylate; v) citrate; vi) succinate; vii) tartrate; viii) lactate; ix) alkyl sulfates: Alk-OS(O)O such as methyl sulfate and ethyl sulfate; x) aryl sulfates: Ar-OS(O)O such as benzene sulfate and toluene sulfate; xi) alkoxysulfates: Alk-OS(O)2O such as methoxysulfate and ethoxysulfate; xii) aryloxysulfates: Ar-OS(O)2O, xiii) phosphate; xiv) acetate; xv) triflate; and xvi) borates such as tetrafluoroborate.

[0054] - The "solvates" represent the hydrates as well as the association with alcohols linear or branched in linear or branched Ci-C4 such as ethanol, isopropanol, n-propanol;

[0055] - By "anhydrous" is meant a quantity of less than 5% by weight of water, preferably less than 3% by weight of water, better less than 1% by weight of water, relative to the total weight of the composition in question; even more preferably, the composition in question is free of water.

[0056] - The terms "coloring agent" and "coloring matter" are equivalent;

[0057] Unless otherwise indicated, the quantities shown are expressed as mass percentages. i) Chitosan compounds

[0058] According to the process of the invention, at least i) a chitosan compound is applied to the keratin fibers. The chitosan compounds according to the invention are compounds comprising at least 2 repeating units, different from each other, of the following general formula (A): in which:

[0059] - RI independently represents a hydrogen atom or a group -(CH2CH(R')Y)qX in which:

[0060] - X denotes a hydrogen atom or a -SO3, M+ radical or an N+(R' i)3 radical, Year - q denotes an integer ranging from 1 to 20,

[0061] - Y designates an oxygen atom or a divalent methylene radical -CH2-; - R' independently represents a hydrogen atom, a methyl group, or a hydroxyl group. - R'i independently represents an alkyl group in C1-C4, - An represents a mineral or organic anion, preferably with a single charge, such as a halide (preferably chloride, bromide), sulfate, sulfonate, carboxylate (preferably acetate, lactate, citrate);

[0062] - M+ represents a mineral or organic cation, preferably with a single charge, such as a alkali metal cation such as sodium or potassium; - R2 represents a hydrogen atom, a -C(O)R”'- group, or a group chosen from -CH2CH(R')-CH2-SO3, M+ or -CH2CH(R')-CH2-N+(R'i)3 , An in which R' is as defined previously and - R”' represents a Ci-C30 hydrocarbon radical, saturated or unsaturated, linear or branched, possibly substituted by at least one hydroxyl group, it being understood that:

[0063] - at least one of the RI radicals is different from a hydrogen atom; and

[0064] - at least one of the radicals RI designates a hydrogen atom; and

[0065] - at least one of the radicals R2 designates a hydrogen atom; and

[0066] - at least one of the R2 radicals is different from a hydrogen atom and different from - CO-CH3; An and M+ being chosen to ensure the electroneutrality of the compounds of formula (A);

[0067] Advantageously, An is an anionic counter-ion selected from among the halides and sulfonates.

[0068] Advantageously, the molecular weight of the chitosan compound i) used in the process according to the invention is in the range from 1,000 g.mol1 to 1,000,000 g.mol1, preferably from 1,000 g.mol1 to 100,000 g.mol1, more preferably from 3,000 g.mol1 to 50,000 g.mol1.

[0069] Preferably, chitosan compounds are compounds comprising at least 2 units, different from each other, of general formula (A) above.

[0070] More preferably, the chitosan compounds i) of the invention are chosen from: a. chitosan compounds of the following formula (Al): in which:

[0071] - RI independently represents a hydrogen atom or a group -(CH2CH(R')O)qH in which: - q denotes an integer ranging from 1 to 20,

[0072] - R' independently represents a hydrogen atom, a methyl group or a hydroxyl group, preferably a hydrogen atom; - R”' represents a C5-C29 hydrocarbon radical, saturated or unsaturated, linear or branched, possibly substituted by at least one hydroxyl group, it being understood that at least one of the RI radicals is different from hydrogen;

[0073] - n is a number representing 50% to 99.9% of the sum n + m + p, - m is a number representing from 0% to 25% of the sum n + m + p, - p is a number representing from 0.1% to 30% of the sum n + m + p, and - the sum n + m + p being equal to 100%.

[0074] In other words, the chitosan (Al) compound comprises two units repeated respectively n and p times, different from each other, and possibly a third unit repeated m times.

[0075] Chitosan compounds of formula (Al) do not comprise any units other than the units repeated n, m and p times respectively.

[0076] Preferably, the chitosan (Al) compound does not comprise a unit repeated m times.

[0077] Preferably, the radical R'" represents a hydrocarbon radical in C7-C2 3, more preferably in Ci rCi 9, better in C13-C17 such as C15. Advantageously, the radical R'" is saturated, in particular linear and more particularly unsubstituted by at least one hydroxyl group.

[0078] Preferably, m is a number representing 0% to 15% of the sum n+m+p, preferably 0% to 10% of the sum n+m+p.

[0079] Preferably, p is a number representing 1% to 15% of the sum n+m+p, preferably 5% to 10% of the sum n+m+p.

[0080] According to a preferred embodiment of the invention, the chitosan compound (Al) is such that: - n is a number representing 70% to 99.9%, better yet 80% to 98%, even better still 85% to 97% of the sum n+m+p, - m is equal to 0%, and - p is a number representing from 0.1% to 30%, or better yet from 3% to 15%, of the sum n+m +p.

[0081] Preferably, the average molecular weight by weight (Mw) of the chitosan compound (Al) is in the range of 10,000 to 1,500,000 g / mol; more preferably from 15,000 to 1,000,000 g / mol; more preferably still from 20,000 to 500,000 g / mol.

[0082] b. chitosan copolymers of the following formula (A2): in which:

[0083] - RI independently represents a hydrogen atom or a group

[0084] -(CH2CH(R')CH2)X in which: - X denotes a radical -SO3, M+ or a radical N+(R'i)3 , An - R' independently represents a hydrogen atom, a methyl group or a hydroxyl group, preferably a hydroxyl radical; - R / independently represents a Ci-C4 alkyl group, preferably methyl; An, M+ are such as defined for formula (A), - R3 represents a hydrogen atom, a -C(O)R”'- group, or a group chosen from -CH2CH(R')-CH2-SO3, M+ or -CH2CH(R')-CH2-N+(R'i)3, An in which R', An, M+ are as defined previously and - R”' represents a C5-C29 hydrocarbon radical, saturated or unsaturated, linear or branched, optionally substituted by at least one hydroxyl group, - n is a number representing 70% to 99% of the sum n + m + p, - m is a number representing 0% to 25% of the sum n + m + p, - p is a number representing 1% to 30% of the sum n + m + p, and - the sum n + m + p being equal to 100%,

[0085] c. and their mixtures.

[0086] Preferably, R' ' ' represents a C7-C27 hydrocarbon radical, saturated or unsaturated, linear or branched, possibly substituted by at least one hydroxyl group, more preferably linear, better linear saturated or unsaturated in C9-C2i, even better linear saturated or unsaturated in Cn-Ci9 such as Ci5 or Ci7;

[0087] Preferably when RI independently represents a hydrogen atom or a -(CH2CH(R')CH2)SO3, M+ group, then R3 represents a hydrogen atom, a group -C(O)R”'-, or a grouping chosen from -CH2CH(R')-CH2-SO3, M+ with R' , M+ , R' ” as defined above.

[0088] Preferably when RI independently represents a hydrogen atom or a group -(CH2CH(R')CH2) N+(R'i)3 , An , then R3 represents a hydrogen atom, a group -C(O)R'”-, or a group chosen from -CH2CH(R')-CH2 - N+(R'i)s, An with R' , R'1, An, R'” as defined above.

[0089] According to a preferred embodiment, the chitosan compounds of formula (A2) do not simultaneously contain -(CH2CH(R')CH2) SO3, M+ and -(CH2 CH(R')CH2) N+(R'i)3 , An group.

[0090] In other words, if the chitosan compounds of formula (A) and (A2) contain at least one -(CH2CH(R')CH2)SO3,M+ group, then they do not contain a -(CH2CH(R')CH2)N+(R'1)3,An group, and if the chitosan compounds of formula (A) and (A2) contain at least one -(CH2CH(R')CH2)N+(R'1)3,An group, then they do not contain a -(CH2CH(R')CH2)SO3,M+ group.

[0091] For example, chitosan compounds of formula (A2) are marketed under the reference Emine®.

[0092] Preferably, the chitosan copolymer(s) of formula (A2) are selected from chitosan lauramide hydroxypropyltrimonium chloride, chitosan stearamide hydroxypropyltrimonium chloride, chitosan isostearamide hydroxypropyltrimonium chloride, chitosan rice branamide hydroxypropyltrimonium chloride, sodium chitosan lauramide hydroxypropylsulfonate, sodium chitosan stearamide hydroxypropylsulfonate, sodium chitosan isostearamide hydroxypropylsulfonate, sodium chitosan rice branamide hydroxypropylsulfonate, and mixtures thereof.

[0093] Preferably, the chitosan compound(s) i) are selected from chitosan (C8-C40)alkylamide hydroxypropyltrimonium salts, chitosan (C8-C40)alkylamide hydroxypropylsulfonate salts, and mixtures thereof; preferably from chitosan (Ci0-C24)alkylamide hydroxypropyltrimonium salts, chitosan (Ci0-C24)alkylamide hydroxypropylsulfonate salts, and mixtures thereof; and more preferably from chitosan (Ci2-Ci8)alkylamide hydroxypropyltrimonium salts, chitosan (Ci2-Ci8)alkylamide hydroxypropylsulfonate salts, and mixtures thereof.

[0094] Advantageously, the chitosan compound(s) i) are in the form of a salt of: - alkali metals such as sodium or potassium, preferably sodium, - halide such as chloride or bromide, preferably chloride, - sulfate, - of sulfonate, - of carboxylate (acetate, lactate, citrate).

[0095] More preferably, the chitosan compound(s) i) are in the form of a salt of: - alkali metals such as sodium or potassium, preferably sodium, - halide such as chloride or bromide, preferably chloride.

[0096] Better, the chitosan compound(s) i) are selected from the chitosan compounds of formula (Al), chitosan lauramide hydroxypropyltrimonium chloride, chitosan stearamide hydroxypropyltrimonium chloride, chitosan isostearamide hydroxypropyltrimonium chloride, chitosan rice branamide hydroxypropyltrimonium chloride, chitosan lauramide hydroxypropylsulfonate sodium, chitosan stearamide hydroxypropylsulfonate sodium, chitosan isostearamide hydroxypropylsulfonate sodium, chitosan rice branamide hydroxypropylsulfonate sodium, and mixtures thereof.

[0097] Preferably, the total content of chitosan compound(s) i) present in a composition is in the range of 0.001% to 20% by weight, preferably 0.005% to 10% by weight, more preferably 0.005% to 5% by weight, better 0.01% to 1% by weight, even better 0.01% to 0.3% by weight, relative to the total weight of the composition containing it / them.

[0098] Preferably, the total content of chitosan compound(s) of formula (Al) present in a composition is in the range of 0.001% to 20% by weight, preferably 0.005% to 10% by weight, more preferably 0.005% to 5% by weight, better 0.01% to 1% by weight, even better 0.01% to 0.3% by weight, relative to the total weight of the composition containing it / them.

[0099] Preferably, the total content of chitosan compound(s) (A2) present in a composition is in the range of 0.001% to 20% by weight, preferably 0.005% to 10% by weight, more preferably 0.005% to 5% by weight, better 0.01% to 1% by weight, even better 0.01% to 0.3% by weight, relative to the total weight of the composition containing it. ii) Compound of formula (I)

[0100] According to the process of the invention, at least one compound of the following formula (I) is applied to the keratin fibers ii): (1i)? - Z - (Y-AK2)m ® [(O)r(AKl)r(OC(O)-C(RA(Rb>C(OhR4)4a

[0101] in which: - Z represents a multivalent hydrocarbon radical in the range C2 to C40, particularly in C3 to C36, linear or branched, saturated or unsaturated, conjugated or not, acyclic or cyclic, aromatic or not, Z possibly being interrupted by one or more heteroatoms or groups chosen from -O-, -N(Ra)-, -S-, -C(O)-, (hetero)cycle(s) and / or their combinations; - AK1 represents a linear or branched divalent hydrocarbon chain saturated or unsaturated in C1-C12, preferably in Ci-C6, more preferably saturated in Ci-C6; - AK2 represents a linear or branched monovalent hydrocarbon chain, saturated or unsaturated, in CrC4o, possibly substituted by one or more identical or different radicals chosen from -OR, -X-AK3-(OC(O)-C(Ra)(Rb)-C(O)-R4)v; and / or said chain being possibly interrupted by one or more heteroatoms or groups chosen from -O-, -S-, -C(O)-, (hetero)cycle(s), and their combinations, in particular -O-(CO)-, -(CO)-O-, -(hetero)cycle-O-(hetero)cycle-; - AK3 represents a linear or branched divalent hydrocarbon chain saturated or unsaturated in C1-C12, preferably in CrC6, more preferentially saturated in Ci-C6, even more preferentially in CrC4; - R represents a hydrogen atom, a linear or branched alkyl radical saturated or unsaturated in Ci-C6, preferably in CrC4, in particular methyl, or a -C(O)-C(Ra)(Rb)-C(O)-R4 radical; - X represents -O-, -S-, -OC(O)- or -C(O)-O-; - Y represents -OC(O)- or -C(O)-O-; - Rj represents a monovalent hydrocarbon radical in C1 to C6, linear or branched, saturated or unsaturated, preferably an (CrC4) alkyl group, in particular methyl or tert-butyl, more preferably methyl; - Ra and Rb, whether identical or different, represent a hydrogen atom or a (Ci-C4)alkyl group, preferably a hydrogen atom; - p denotes an integer equal to 0 or 1; - m denotes an integer equal to 0, 1, 2, 3 or 4; it being understood that when m is greater than 1, then the radicals -Y-AK2 are identical or different; - n denotes an integer equal to 0, 1, 2, 3 or 4; it being understood that when n is greater than 1, then the radicals -(O)t-(AKi)q-(OC(O)-C(Ra)(Rb)-C(O)-R4)u are identical or different; -1 denotes an integer equal to 0 or 1; - q denotes an integer equal to 0 or 1; - u denotes an integer equal to 1, 2 or 3; - v denotes an integer equal to 1, 2 or 3; given that if q is equal to 0 then t is equal to 0, that (m + n) is greater than or equal to 1, and that the compounds of formula (I) contain at least two -C(O)-C(Ra)(Rb)-C(O)-R4 groups).

[0102] The compound(s) of formula (I) include their optical, geometric and / or solvated isomers, such as hydrates.

[0103] The compound(s) of formula (I) may be such that Z denotes a radical chosen from: a) divalent radicals, preferably C2-C30, possibly interrupted by one or more heteroatoms or groups chosen from -O-, -N(Ra)-, -S-, -C(O)- and / or (hetero)cycle(s), in particular the radicals -CH2-(CH2)f, in which f denotes an integer between 1 and 10, preferably between 1 and 5, or such as the radicals -(CH2)g-(heterocycle)-O-(CH2)h-(heterocycle)-(CH2)j-, in which h denotes 0, 1 or 2, preferably 0 or 1, and g and j independently denote an integer between 1 and 3, preferably 1; b) trivalent radicals, preferably C3-C6, in particular CH2-CH-CH2-; and (c) tetravalent radicals, preferably in C3-Ci2, in particular -CH2-C-CH2-CH2-CH2-, or -CH2-C-CH2- or radicals -(CH2)a-CH-CH-(CH2)b-, in which a and b independently denote an integer equal to 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10, preferably a is greater than b.

[0104] Advantageously, a (hetero)cycle in the sense of the invention means a heterocyclic divalent radical, preferably a heterocycloalkyl radical, more particularly a heterocycloalkyl divalent radical comprising 3, 5 or 6 links such as an epoxide divalent radical, a tetrahydrofuran divalent radical or a tetrahydropyran divalent radical, said (hetero)cycle being optionally substituted by one or more radicals chosen from -OR with R as defined above, and in particular -OH or -OC(O)-C(Ra)(Rb)-C(O)-R4).

[0105] Preferably, AK2 represents a linear or branched monovalent hydrocarbon chain, saturated or unsaturated, in Ci2-C28, optionally substituted by one or more identical or different radicals chosen from -OR, -X-AK3-(OC(O)-C(Ra) (Rb)-C(O)-R4)v, and / or said chain being optionally interrupted by -OC(O)- or -C(O)-O-,

[0106] Preferably, the compound(s) of formula (I), as well as their optical, geometric and / or solvated isomers, such as hydrates, are such that: - Z represents the trivalent radical -CH2-CH- CH2-; - p is equal to 0; - n is equal to 0; - m is equal to 3; - AK2 represents a linear or branched monovalent hydrocarbon chain, saturated or unsaturated, in Ci2-C24j possibly substituted by one or more identical or different radicals chosen from -OR, -X-AK3-(OC(O)-C(Ra)(Rb)-C(O)-R4)v, and / or said chain possibly being interrupted by one or more heteroatoms or groups chosen from -O-, -S-, -C(O)-, epoxides, and their combinations, in particular -O(CO)- or -C(O)-O-; - Y, AK3, v, R, X, R4, Ra and Rb being such as defined previously for formula (i); it being understood that the compounds contain at least 2 radicals -C(O)-C(Ra)(Rb)-C(O)-R4.

[0107] In particular, Y denotes -OC(O)-.

[0108] In particular, AK2 may represent a linear or branched monovalent hydrocarbon chain, saturated or unsaturated, in C12-C24 optionally substituted by one or more identical or different radicals chosen from -OR, -X-AK3-(OC(O)-C(Ra)(Rb)-C(O)-R4)v, and / or said chain being optionally interrupted by one or more heteroatoms or groups chosen from -O-, -S-, -C(O)-, and their combinations, in particular -OC(O)- or -C(O)-O-.

[0109] Advantageously, the compound(s) of formula (I) are in particular chosen from compounds (1), (2), (3), (4), (7), (8), (9), (11) and (16) below, as well as their optical, geometric and / or solvated isomers, such as hydrates: (1)

[0110] Preferably, the compound(s) of formula (I), as well as their optical, geometric and / or solvated isomers, such as hydrates, can also be such that: - p is equal to 0; - Z represents a multivalent hydrocarbon radical in C4 to C24, particularly in C6 to C2oplus particularly in CM to C20, in particular Cp, linear or branched, saturated or unsaturated preferably saturated, acyclic, Z being further possibly substituted by one or more radicals -[(O)t-(AKl)q- (OC(O)-C(Ra)(Rb)-C(O)-R4)u]n; - n denotes an integer equal to 0, 1, 2, 3 or 4; it being understood that when n is greater than 1, then the radicals -(0)t-(AKi)q-(0-C(0)-C(Ra)(Rb)-C(0)-R4)u are identical or different; preferably n is non-zero; - m is equal to 1; - AK2 represents a linear or branched monovalent hydrocarbon chain, saturated or unsaturated, preferably saturated, in C3-C8, in particular C4 or C6, substituted by one or more identical or different radicals chosen from -OR, -X-AK3-(OC(O)-C(Ra)(Rb)-C(O)-R4)v, preferably substituted by one or more -OR radicals; and / or said chain being optionally interrupted by one or more heteroatoms or groups chosen from -O-, -S-, -C(O)-, (hetero)cycle(s), and their combinations, in particular -OC(O)-, -C(O)-O-, -(hetero)cycle-O-(hetero)cycle-, and preferably being uninterrupted; - Y, AK1, AK3, t, q, u, v, R, X, R4, Ra and Rb being such as defined previously for formula (I); it being understood that said compound contains at least 2 radicals -C(O)-C(Ra)(Rb)-C(O)-R 4*

[0111] The compound(s) of formula (I) are in particular chosen from compounds (5) and (6) below, as well as their optical, geometric and / or solvated isomers, such as hydrates:

[0112] Preferably, the compound(s) of formula (I), as well as their optical, geometric and / or solvated isomers, such as hydrates, may also be such that: - p is equal to 0; - n + m is equal to 4, m being non-zero; - Z represents a tetravalent radical, hydrocarbon in C2 to C24, particularly in C3 to C10, especially C3, unsubstituted and uninterrupted, linear or branched, saturated or unsaturated, preferably saturated and acyclic; - AK2 independently represent a linear or branched monovalent hydrocarbon chain, saturated or unsaturated, preferably saturated, in C12-C24, preferably in C16-C20, in particular C[8], optionally substituted by one or more identical or different radicals selected from -OR and -X-AK3-(OC(O)-C(Ra)(Rb)-C(O)-R4)v, preferably substituted by one or more -X-AK3-(OC(O)-C(Ra)(Rb)-C(O)-R4)v radicals; and / or said chain being optionally interrupted by one or more heteroatoms or groups selected from -O-, -S-, -C(O)-, (hetero)cycle(s), and their combinations, in particular -OC(O)-, -C(O)-O-, -(hetero)cycle-O-(hetero)cycle-, and preferably being uninterrupted; - AK3 represents a linear or branched divalent hydrocarbon chain saturated or unsaturated in C1-C12, preferably in CrC6, more preferentially saturated in Ci-C6, even more preferentially in C2-C4, better in C3; - v is such as defined previously for formula (I); preferably v is equal to 2; - X is as defined previously for formula (I); preferably X denotes a sulfur atom; - Y, AK1, u, t, q, R, R4, Ra and Rb are as defined previously for formula (i); it being understood that said compound contains at least 2 radicals -C(O)-C(Ra)(Rb)-C(O)-R 4*

[0113] More preferably, m is equal to 3, n is equal to 1 and u is equal to 1.

[0114] More preferably, t is equal to 0.

[0115] More preferably, q is equal to 0.

[0116] More preferably, Y denotes -C(O)-O.

[0117] More preferably, none of the AK2 radicals are interrupted.

[0118] More preferably, the AK2 radicals are saturated.

[0119] More preferably, the AK2 radicals are not substituted by -OR.

[0120] In particular, AK3 can represent a linear or branched divalent hydrocarbon chain saturated or unsaturated in Ci-C6, more preferentially saturated in Ci-C6, even more preferentially saturated in C1-C4, better saturated in C3.

[0121] Advantageously, the compound(s) of formula (I) are in particular chosen from the compounds (10) below, as well as their optical, geometric and / or solvated isomers, such as hydrates:

[0122] Preferably, the compound(s) of formula (I), as well as their optical, geometric and / or solvated isomers, such as hydrates, may also be such that: - p is equal to 1; - Z represents a multivalent hydrocarbon radical in CM to C24, particularly in Ci6 to C2o, preferably Cp, linear or branched, saturated or unsaturated, preferably saturated and acyclic; Z being further possibly substituted by one or more radicals -[(O)t-(AKl)q-(OC(O)-C(Ra)(Rb)-C(O)-R4)u]n, preferably being unsubstituted; - AK2 represents a linear or branched monovalent hydrocarbon chain, saturated or unsaturated, preferably saturated, in C8-C30, preferably in C10-C29, substituted by one or more identical or different radicals selected from -OR, -X-AK3-(OC(O)-C(Ra)(Rb)-C(O)-R4)v, preferably substituted by one or more -OR radicals; and / or said chain being optionally interrupted by one or more heteroatoms or groups selected from -O-, -S-, -C(O)-, (hetero)cycle(s), and their combinations, in particular -OC(O)-, -C(O)-O-, -(hetero)cycle-O-(hetero)cycle-, preferably being interrupted by -OC(O)- or -C(O)-O-; - X is as defined previously for formula (I), preferably X denotes a sulfur atom; - Y, AK1, AK3, n, m, v, t, q, u, R, R4, Ra and Rb being such as defined previously for formula (I); it being understood that said compound contains at least 2 C(O)-C(Ra)(Rb)-C(O)-R radicals 4*

[0123] More preferably, n is equal to 0 and m is equal to 1.

[0124] More preferably, Z is a divalent radical.

[0125] More preferably, if Z is an unsaturated chain, AK2 is an unsaturated chain, and if Z is a saturated chain, AK2 is a saturated chain.

[0126] In particular, the compound(s) of formula (I), as well as their optical, geometric and / or solvated isomers, such as hydrates, may have the formula (link): HZY-AK4-Y'-ZH (link) formula (link) in which: - Y is such as defined previously for formula (I); - Z represents a divalent hydrocarbon radical in C2 to C24, in particular in C4 to C2o, preferably in C5 or Cp, linear or branched, saturated or unsaturated, preferably saturated; - Y' represents -C(O)-O- or -OC(O)- it being understood that if Y represents -OC(O)-, Y' represents -C(O)-O-, and if Y represents -C(O)-O-, Y' represents -OC(O)-; - AK4 designates a saturated divalent hydrocarbon radical of 5 or 6 carbon atoms, substituted by at least two -OR radicals with R being as defined previously in formula (I); it being understood that the compounds of formula (lie) contain at least 2 radicals -C(O)-C(Ra)(Rb)-C(O)-R4, and preferably 4 radicals -C(O)-C(Ra)(Rb)-C(O)-R4.

[0127] Advantageously, the compound(s) of formula (I) are in particular chosen from compounds (12) and (15) below, as well as their optical, geometric and / or solvated isomers, such as hydrates: (12) (15).

[0128] Preferably, the compound(s) of formula (I), as well as their optical, geometric and / or solvated isomers, such as hydrates, may also be such that: - p is equal to 0; - Z represents a tetravalent hydrocarbon radical in C2 to C24, in particular in C3 to C10, preferably in C4 or C5, linear or branched, saturated or unsaturated, preferably saturated and acyclic, Z being further substituted by one or more radicals -[(O)t-(AKl)q-(OC(O)-C(Ra)(Rb)-C(O)-R4)u]n, preferably n being equal to 1; - n + m equals 4, preferably m equals 3; - AK2 independently represents a linear or branched hydrocarbon chain, saturated or unsaturated, preferably saturated, in CM to C30, preferably from C16 to C24, preferably in Cp, said chain optionally being substituted by one or more identical or different radicals selected from -OR, -X-AK3-(OC(O)-C(Ra)(Rb)-C(O)-R4)v, preferably substituted by one or more -OR radicals; and / or said chain optionally being interrupted by one or more heteroatoms or groups selected from -O-, -S-, -C(O)-, (hetero)cycle(s), and their combinations, in particular -OC(O)- or -C(O)-O-, -(hetero)cycle-O-(hetero)cycle-, preferably being uninterrupted; - X is as defined previously for formula (I), and preferably X denotes a sulfur atom; - Y, AK1, AK3, u, t, q, v, n, m R, R4, Ra and Rb being such as defined previously for formula (I); it being understood that said compound contains at least 2 C(O)-C(Ra)(Rb)-C(O)-R radicals 4*

[0129] More preferably, t is equal to 0 and u is equal to 1.

[0130] More preferably, all AK2 radicals are identical, and preferably, all The radicals Y are identical.

[0131] More preferably, Y denotes -OC(O)-.

[0132] In particular, compounds of formula (I), as well as their optical, geometric and / or solvated isomers, such as hydrates, may have the following general formula (lid):

[0133] [AK'2-OCO-CH2]3-C-CH2-OC(O)-C(Ra)(Rb)-C(O)-R4 (lid)

[0134] formula (lid) wherein AK'2 represents a linear or branched monovalent hydrocarbon chain, preferably linear, saturated or unsaturated, preferably saturated, in Ci4-C3o, preferably in Ci6-C24, preferably in Cp, said chain being substituted by one or more identical or different radicals selected from -OR, -S-AK3-(OC(O)-C(Ra)(Rb)-C(O)-R4)v, preferably substituted by one or more -OR radicals; AK3, v, R, R4, Ra and Rb being such as defined above for formula (I), it being understood that said compounds contain at least 2 C(O)-C(Ra)(Rb)-C(O)-R4 radicals.

[0135] Preferably, the compound(s) of formula (I), as well as their optical, geometric and / or solvated isomers, such as hydrates, can be such that: - p is equal to 0; - m is non-zero; - Z represents a divalent hydrocarbon radical in C2 to C24, in particular in C3 to C[2 , linear or branched, saturated or unsaturated, conjugated or not, preferably not conjugated, acyclic or cyclic, aromatic or not, preferably not aromatic, said radical Z being further interrupted by one or more heteroatoms or groups chosen from -O-, -N(Ra)-, -S-, -C(O)-, heterocycloalkyl(s) comprising 5 or 6 links, and their combinations; - AK2 represents a linear or branched monovalent hydrocarbon chain, saturated or unsaturated, preferably saturated, in Ci4-C30, preferably in Ci4-C24, more preferably in Ci5, said chain being optionally substituted by a or several identical or different radicals chosen from -OR and -X-AK3-(OC(O)-C(Ra)(Rb)-C(O)-R4)v, preferably unsubstituted; and / or said chain being optionally interrupted by one or more heteroatoms or groups chosen from -O-, -S-, -C(O)-, (hetero)cycles, and their combinations, in particular -OC(O)-, -C(O)-O- or -(hetero)cycle-O-(hetero)cycle-, preferably optionally interrupted by -OC(O)- or -C(O)-O-, and more preferably being uninterrupted; - X is as defined previously for formula (I), and preferably X denotes a sulfur atom; - Y, AK1, AK3, v, t, q, u, R, R4, Ra and Rb being such as defined previously for formula (I), it being understood that said compound contains at least 2 C(O)-C(Ra)(Rb)-C(O)-R radicals 4*

[0136] More preferably, Z denotes a divalent radical -(CH2)g-(heterocycle)-O-(CH2)h-(heterocycle)-(CH2)j- in which h is equal to 0, 1 or 2, preferably is equal to 0 or 1, g and j independently denote an integer between 1 and 3, preferably 1, (heterocycle) denotes a heterocycloalkyl divalent radical comprising 5 or 6 links, in particular a divalent radical of tetrahydrofuran or a divalent radical of tetrahydropyran, said heterocycle being optionally substituted by one or more radicals selected from -OR, with R as defined above for formula (I), and in particular -OH or -OC(O)-C(Ra)(Rb)-C(O)-R4).

[0137] In particular, compounds of formula (I), as well as their optical, geometric and / or solvated isomers, such as hydrates, may have the following general formula (link): AK”2-C(O)-O-(CH2)g-(heterocycle)-O-(CH2)h-(heterocycle)-(CH2)jO-CO-AK”2(Iie) formula (link) in which: - h is equal to 0, 1 or 2, preferably is equal to 0 or 1; - g and j independently denote an integer between 1 and 3, preferably 1; - (heterocycle) designates a heterocycloalkyl divalent radical comprising 5 or 6 substituted links by one or more identical or different radicals chosen from -OR, with R as defined previously for formula (I), and in particular -OH or -OC(O)-C(Ra)(Rb)-C(O)-R4); - AK” 2 represents a linear or branched monovalent hydrocarbon chain, saturated or unsaturated, preferably saturated, in Ci4-C30, preferably in Ci4-C24, more preferably in Ci5, said chain being optionally substituted by one or more identical or different radicals chosen from -OH, -OC(O)-C(Ra)(Rb)-O(O)-1^) and -S-AK3-(OC(O)-C(Ra)(Rb)-C(O)-R4)v, preferably unsubstituted; and / or said chain being possibly interrupted by one or more heteroatoms or groups chosen from -O-, -S-, -C(O)-, (hetero)cycle(s), and their combinations, in particular -OC(O)-, -C(O)-O- or -(hetero)cycle-O-(hetero)cycle-, preferably possibly interrupted by -OC(O)- or -C(O)-O-, and more preferably being uninterrupted; it being understood that said compound contains at least 2 radicals -C(O)-C(Ra)(Rb)-C(O)-R

[0138] 4* Advantageously, compounds of formula (I) or (lie) are in particular chosen from the compounds (14) below, as well as their optical, geometric and / or solvated isomers, such as hydrates:

[0139]

[0140] with W being a hydrogen atom or -C(O)-C(Ra)(Rb)-C(O)-R4, and said compound containing at least two -C(O)-C(Ra)(Rb)-C(O)-R4 groups. Advantageously, the compound(s) of formula (I) are chosen from compounds (1) to (16) below, as well as their optical, geometric and / or solvated isomers, such as hydrates: Q (4) ■A. (12) (16)

[0141] with W being a hydrogen atony or -C(O)-C(Ra)(Rb)-C(O)-R4, and said compound containing at least two -C(O)-C(Ra)(Rb)-C(O)-R4 groups.

[0142] According to a particular embodiment of the invention, the compound(s) of formula (I) are chosen from the compounds (1) to (14) above.

[0143] Preferably, the compound(s) of formula (I) are chosen from compounds (1), (3), (4), (8), (9), (10), (11), (15) and (16) below: (15)

[0144]

[0145]

[0146] More preferably, the compound(s) of formula (I) are chosen from the compounds (1), (3), (4), (8), (9), (10) and (11) above. Preferably, compounds of formula (I) may also be chosen from the following compounds of formula (la): Z-(Y-AK2)3 (la) formula (the) in which: - Z represents -CH2-CH-CH2- ; - AK2 independently designates a linear or branched monovalent hydrocarbon chain, saturated or unsaturated, in Ci2-C24, possibly substituted by one or more identical or different radicals chosen from -OR and -X-AK3-(OC(O)-C(Ra)(Rb)-C(O)-R4)v; and / or said chain being possibly interrupted by one or more heteroatoms or groups chosen from -O-, -S-, -C(O)-, epoxides, and their combinations, in particular -OC(O)- and -C(O)-O-; - Y, AK3, v, R, X, R4, Ra and Rb being such as defined previously in formula (I), preferably Y denotes -OC(O); it being understood that said compound contains at least 2 C(O)-C(Ra)(Rb)-C(O)-R radicals in particular with the exception of compounds (1), (2), (3), (4) and (7) as defined above.

[0147] In particular, the compound(s) of formula (la) are chosen from compounds (8), (9), (11) and (16) as defined above.

[0148] More preferably, the compound(s) of formula (la) are the compounds for which: (a) at least one of the 3 radicals AK2 designates a branched monovalent hydrocarbon chain, saturated or unsaturated, in the form Ci2-C24, optionally substituted by one or more identical or different radicals selected from -OR and -X-AK3-(OC(O)-C(Ra)(Rb)-C(O)-R4)v; and / or said chain being optionally interrupted by one or more heteroatoms or groups selected from -O-, -S-, -C(O)-, (hetero)cycle(s), in particular epoxides, and their combinations, in particular -OC(O)- or -C(O)-O-; AK3, v, R, X, R4, Ra and Rb being as defined above; it being understood that said compound contains at least 2 C(O)-C(Ra)(Rb)-C(O)-R4 radicals; preferably Y represents -OC(O); preferably X represents S; preferably the 3 AK2 chains have from 15 to 21 carbon atoms, more preferably 17 carbon atoms; and preferably none of the 3 AK2 radicals is interrupted; or b) the 3 radicals AK2 independently represent a linear, saturated, Ci2-C24 hydrocarbon chain, substituted by at least one radical chosen from -OH and OR', and possibly substituted by one or more identical or different radicals chosen from -OC(O)-C(Ra)(Rb)-C(O)-R4 and -X'-AK3-(OC(O)-C(Ra)(Rb)-C(O)-R4)v; R' denoting a C2-C6 alkyl radical, in particular ethyl; AK3, v, R, R4, Ra and Rb being as defined above, preferably Y denotes -OC(O)-; and X' represents -O- or -C(O)-O-; it being understood that said compound contains at least 2 radicals -C(O)-C(Ra)(Rb)-C(O)-R4; preferably the 3 AK2 chains comprise from 15 to 21 carbon atoms, more preferably 17 carbon atoms; and preferably none of the 3 AK2 radicals is interrupted; or (c) The AK2 radicals independently represent a linear, saturated, monovalent hydrocarbon chain, in Ci2-C24, optionally substituted by one or more identical or different radicals selected from -OR and -X-AK3-(OC(O)-C(Ra)(Rb)-C(O)-R4)v; said chain being interrupted by one or more heteroatoms or groups selected from -O- and / or -S- and / or -C(O)-, (hetero)cycle(s), in particular one or more epoxides, and their combinations, preferably -OC(O)-, -C(O)-O- and -(hetero)cycle-O-(hetero)cycle-; AK3, v, R, X, R4, Ra and Rb being as defined above; and it being understood that said compound contains at least 2 C(O)-C(Ra)(Rb)-C(O)-R4 radicals; preferably Y represents -OC(O)-; preferably X represents S; preferably the 3 AK2 chains comprise from 15 to 21 carbon atoms, more preferably 17 carbon atoms; or d) the 3 AK2 radicals are such that at least one of the 3 AK2 radicals represents a linear or branched monovalent hydrocarbon chain, unsaturated in Ci2-C24, optionally substituted by one or more identical or different radicals chosen from -OR, said chain being optionally interrupted by one or more heteroatoms or groups chosen from -O-, -S-, -C(O)-, (hetero)cycle(s), and their combinations, in particular -OC(O)-, -C(O)-O- or (hetero)cycle-O-(hetero)cycle; and at least one of the 3 radicals AK2 represents a linear or branched monovalent hydrocarbon chain, saturated in Ci2-C24, substituted by one or more identical or different radicals chosen from -S-AK3-(OC(O)-C(Ra)(Rb)-C(O)-R4)v and possibly substituted by one or more identical or different radicals chosen from -OR; AK3, v, R, R4, Ra and Rb being as defined above, preferably Y denotes -OC(O)-;provided that said compound contains at least 2 radicals -C(O)-C(Ra)(Rb)-C(O)-R4; preferably Y represents -OC(O)-; preferably X represents S; preferably the 3 AK2 chains comprise from 15 to 21 carbon atoms, more preferably 17 carbon atoms; preferably none of the 3 AK2 radicals is interrupted; or; e) the 3 radicals AK2 are such that AK2 represents a linear monovalent hydrocarbon chain saturated with Ci2-C24 substituted by one or more identical or different radicals chosen from -S-AK3-(OC(O)-C(Ra)(Rb)-C(O)-R4)v; said chain being optionally interrupted by one or more heteroatoms or groups chosen from -O-, -S-, -C(O)-, (hetero)cycle(s), and their combinations, such as -OC(O)-, -C(O)-O-, (hetero)cycle-O-(hetero)cycle; AK3 represents a linear or branched divalent hydrocarbon chain saturated or unsaturated with C3-Ci2, preferably with C3-C6, more preferably saturated with C3-C6, in particular with C3; v, R4, Ra and Rb being as defined above, preferably Y denotes -OC(O)-; provided that the said compound contains at least 2 radicals -C(O)-C(Ra)(Rb)-C(O)-R4; preferably Y represents -OC(O)-; preferably v is equal to 2;preferably the 3 AK2 chains comprise from 15 to 21 carbon atoms, more preferably 17 carbon atoms; preferably none of the 3 AK2 radicals is interrupted; preferably the AK2 radicals are saturated; preferably AK3 denotes a trivalent radical -CH2-CH-CH2-; or; f) the 3 AK2 radicals represent a linear, saturated, monovalent hydrocarbon chain, in Ci2-C24, substituted by one or more identical or different radicals -OC(O)-AK3-(OC(O)-C(Ra)(Rb)-C(O)-R4)v, said chain being further possibly substituted by one or more identical or different radicals chosen from -OR and -S-AK3-(OC(O)-C(Ra)(Rb)-C(O)-R4)v and / or said chain being optionally interrupted by one or more heteroatoms or groups selected from -O-, -S-, -C(O)-, (hetero)cycle(s) and their combinations, in particular -OC(O)-, -C(O)-O- or -(hetero)cycle-O-(hetero)cycle-; AK3, v, R4, Ra and Rb being such as defined above, preferably Y denotes -OC(O)-; it being understood that said compound contains at least 2 -C(O)-C(Ra)(Rb)-C(O)-R4 radicals; preferably Y represents -OC(O)-; preferably v is equal to 1 or 2, more preferably is equal to 1; preferably the 3 AK2 chains comprise from 15 to 21 carbon atoms, more preferably 17 carbon atoms; preferably none of the 3 AK2 radicals are interrupted; preferably the AK2 radicals are saturated; preferably the AK2 radicals are substituted by at least one -OR radical, preferably at least one -OC(O)-C(Ra)(Rb)-C(O)-R4 radical;preferably AK2 is not substituted by -S-AK3-(OC(O)-C(Ra)(Rb)-C(O)-R4)v; preferably AK3 represents a linear or branched hydrocarbon chain saturated or unsaturated in Ci-C6, more preferably saturated in Ci-C6, even more preferably in C2.

[0149] Preferably, the compound(s) of formula (I) may be chosen from the following compounds of formula (Ib):

[0150] m(AK2 -Y) - Z - [(O)t-(AKl)q-(OC(O)-C(Ra)(Rb)-C(O)-R4)u]n (Ib)

[0151] formula (Ib) in which: - n + m is equal to 4, m being non-zero; m and n being such as defined previously for compounds of formula (I); - Z represents a tetravalent hydrocarbon radical in C2 to C24, in particular in C3 to C10, preferably in C3, unsubstituted and uninterrupted, linear or branched, saturated or unsaturated, preferably saturated and acyclic; - AK2 independently represent a linear or branched monovalent hydrocarbon chain, saturated or unsaturated, preferably saturated, in C[2-C24, preferably in Ci6-C20, preferably in Ci8, optionally substituted by one or more identical or different radicals chosen from -OR, -X-AK3-(OC(O)-C(Ra)(Rb)-C(O)-R4)v, preferably substituted by one or more radicals -X-AK3-(OC(O)-C(Ra)(Rb)-C(O)-R4)v; and / or said chain being optionally interrupted by one or more heteroatoms or groups chosen from -O-, -S-, -C(O)-, (hetero)cycle(s), and their combinations, in particular -OC(O)-, -C(O)-O- or -(hetero)cycle-O-(hetero)cycle-, preferably being uninterrupted; - AK3 represents a linear or branched divalent hydrocarbon chain saturated or unsaturated in CrCi2, preferably in CrC6, more preferentially saturated in Ci-C6, even more preferentially in C2-C4, preferably in C3; - v is such as defined previously, preferably v is equal to 2; - X is as defined previously, preferably X designates a sulfur atom; - Y, AK1, t, q, u, R, R4, Ra and Rb being as defined previously; it being understood that said compound contains at least 2 radicals -C(O)-C(Ra)(Rb)-C(O)-R 4*

[0152] More preferably, m is equal to 3, n is equal to 1 and u is equal to 1.

[0153] More preferably, t is equal to 0 and q is equal to 0.

[0154] More preferably, Y denotes -C(O)-O-.

[0155] More preferably, none of the AK2 radicals are interrupted.

[0156] More preferably, the AK2 radicals are saturated.

[0157] More preferably, the AK2 radicals are not substituted by -OR.

[0158] In particular, AK3 can represent a linear or branched hydrocarbon chain saturated or unsaturated in Ci-C6, more preferably saturated in Ci-C6, even more preferably in C1-C4, and even better in C3.

[0159] Advantageously, compounds of formula (I) or (Ib) are in particular chosen from compounds (10) as defined above, as well as their optical, geometric and / or solvated isomers, such as hydrates.

[0160] Preferably, the compound(s) of formula (I) may be chosen from the following compounds of formula (le), as well as their optical, geometric and / or solvated isomers, such as hydrates:

[0161] m(AK2 -Y) - ZH - [(O)t-(AKl)q-(OC(O)-C(Ra)(Rb)-C(O)-R4)u]n (the)

[0162] formula (the) in which: - Z represents a multivalent hydrocarbon radical in CM to C24, particularly in Ci6 to C20 such as Cp, linear or branched, saturated or unsaturated, preferably saturated and acyclic, Z being further possibly substituted by one or more radicals -[(O) t-(AKl)q-(OC(O)-C(Ra)(Rb)-C(O)-R4)u]n, preferably unsubstituted; - AK2 represents a linear or branched monovalent hydrocarbon chain, saturated or unsaturated, preferably saturated, in Ci4-C30, preferably in C20-C29, substituted by one or more identical or different radicals chosen from -OR and -X-AK3-(OC(O)-C(Ra)(Rb)-C(O)-R4)v, preferably substituted by one or more -OR radicals; and / or said chain being optionally interrupted by one or more heteroatoms or groups chosen from -O-, -S-, -C(O)-, (hetero)cycle(s), and their combinations, in particular -OC(O)-, -C(O)-O- or (hetero)cycle-O-(hetero)cycle, preferably interrupted by -OC(O)- or -C(O)-O-; - X is as defined previously, and preferably X designates a sulfur atom; - Y, AK1, AK3, n, m, v, t, q, u, R, R4, Ra and Rb being as defined previously; it being understood that said compound contains at least 2 radicals -C(O)-C(Ra)(Rb)-C(O)-R

[0163] More preferably, n is equal to 0 and m is equal to 1.

[0164] More preferably, Z is a divalent radical.

[0165] More preferably, if Z is an unsaturated chain, AK2 is an unsaturated chain and if Z is a saturated chain, AK2 is a saturated chain.

[0166] Preferably, the compound(s) of formula (the), as well as their optical, geometric and / or solvated isomers, such as hydrates, are in particular of formula (the) as defined above.

[0167] Advantageously, the compound(s) of formula (lie) are in particular chosen from the compounds (12) as defined above, as well as their optical, geometric and / or solvated isomers, such as hydrates.

[0168] Preferably, the compound(s) of formula (I) may be chosen from the following compounds of formula (Id), as well as their optical, geometric and / or solvated isomers, such as hydrates:

[0169] m(AK2 -Y) - Z - [(O)t-(AKl)q-(OC(O)-C(Ra)(Rb)-C(O)-R4)u]n (Id)

[0170] formula (Id) in which: - n + m equals 4, preferably m equals 3; - Z represents a tetravalent hydrocarbon radical in C2 to C24, in particular in C3 to Cio, in particular in C4 or C5, linear or branched, saturated or unsaturated, preferably saturated or acyclic, Z being further substituted by one or more radicals -[(O)t-(AKl)q-(OC(O)-C(Ra)(Rb)-C(O)-R4)u]n, preferably n is equal to 1; - AK2 independently represents a linear or branched monovalent hydrocarbon chain, saturated or unsaturated, preferably saturated, in Ci4-C30, preferably in Ci6-C24, preferably in Cp, said chain being optionally substituted by one or more identical or different radicals chosen from -OR or -X-AK3-(OC(O)-C(Ra)(Rb)-C(O)-R4)v, preferably substituted by one or more -OR radicals; and / or said chain being optionally interrupted by one or more heteroatoms or groups chosen from -O-, -S-, -C(O)-, (hetero)cycle(s), and their combinations, in particular -OC(O)-, -C(O)-O- or (hetero)cycle-O-(hetero)cycle, preferably being uninterrupted; X is as defined above, preferably X designates a sulfur atom; Y, AK1, AK3, v, R, R4, Ra and Rb being as defined previously, it being understood that these compounds contain at least 2 radicals -C(O)-C(Ra)(Rb)-C(O)-R4.

[0171] More preferably, t is equal to 0 and u is equal to 1.

[0172] More preferably, all AK2 radicals are identical.

[0173] More preferably, all radicals Y are identical.

[0174] Even more preferentially, Y denotes -OC(O)-.

[0175] Preferably, compounds of formula (Id), as well as their optical, geometric and / or solvated isomers, such as hydrates, are in particular of formula (lid), as defined above.

[0176] Preferably, the compound(s) of formula (I) may be chosen from the following compounds of formula (le), as well as their optical, geometric and / or solvated isomers, such as hydrates:

[0177] m(AK2-Y) - Z - [(O)t-(AKl)q-(OC(O)-C(Ra)(Rb)-C(O)-R4)u]n (the)

[0178] formula (the) in which: - n + m is equal to 2, m being non-zero, preferably m being equal to 2; n is such as defined previously for compounds of formula (I), preferably n is zero; - Z represents a divalent hydrocarbon radical in C2 to C24, in particular in C3 to Ci2, linear or branched, saturated or unsaturated, conjugated or not, preferably not conjugated, acyclic or cyclic, aromatic or not, preferably not aromatic, said radical Z being further interrupted by one or more heteroatoms or groups chosen from -O-, -N(Ra)-, -S-, -C(O)-, (hetero)cycle(s), and their combinations; preferably Z denotes a divalent radical -(CH2)g-(heterocycle)-O-(CH2)h-(heterocycle)-(CH2)j- in which h denotes 0, 1 or 2, preferably 0 or 1, g and j independently denote an integer between 1 and 3, preferably 1; (heterocycle) denotes a heterocyclic divalent radical (i.e. a heterocycle), preferably a heterocycloalkyl radical, more particularly a heterocycloalkyl divalent radical comprising 5 or 6 links, in particular a divalent radical of tetrahydrofuran or a divalent radical of tetrahydropyran, said heterocycle being optionally substituted by one or more radicals chosen from -OR with R as defined above, and in particular -OH or -OC(O)-C(Ra)(Rb)-C(O)-R4); - AK2 represents a linear or branched monovalent hydrocarbon chain, saturated or unsaturated, preferably saturated, in Ci4-C30, preferably Ci4-C24, preferably in Cp, said chain being optionally substituted by one or more identical or different radicals chosen from -OR and -X-AK3-(OC(O)-C(Ra)(Rb j-QOj-RJv, preferably unsubstituted; and / or said chain being optionally interrupted by one or more heteroatoms or groups chosen from -O-, -S-, -C(O)-, (hetero)cycle(s), and their combinations, in particular -OC(O)-, -C(O)-O- or -(hetero)cycle-O-(hetero)cycle-, preferably possibly interrupted by -OC(O)- or -C(O)-O-, and more preferably uninterrupted; - X is as defined previously, preferably X denotes a sulfur atom; - Y, AK1, AK3, v, t, q, u, R, R4, Ra and Rb being as defined previously; it being understood that said compound contains at least 2 C(O)-C(Ra)(Rb)-C(O)-R radicals

[0179] Preferably, the compounds of formula (the), as well as their optical, geometric and / or solvated isomers, such as hydrates, are in particular of formula (the) as defined above.

[0180] Preferably, the total content of compound(s) of formula (I) present in a composition is in the range of 0.1% to 60% by weight, preferably 1% to 40% by weight, and more preferably 3% to 20% by weight, relative to the total weight of the composition containing it / them.

[0181] Preferably, the total content of compound(s) of formula (I), (la), (Ib), (le), (Id), (le), (lie), (lid) or (lie), as defined above, present in a composition, is in the range of 0.1% to 60% by weight, preferably 1% to 40% by weight, and more preferably 3% to 20% by weight, relative to the total weight of the composition containing it / them.

[0182] Preferably, the total content of compound(s) (1) to (16) present in a composition is in the range of 0.1% to 60% by weight, preferably 1% to 40% by weight, and more preferably 3% to 20% by weight, relative to the total weight of the composition containing it / them. Preparation of compounds of formula (I)

[0183] In particular, the compound(s) of formula (I), or (la), (Ib), (le), (Id), (le), (lie), (lid) or (lie), can be prepared by the following sequence of reactions: First step

[0184] In a first step, a commercial polyol, preferably natural, of formula (H)pZ(OH)m- is reacted with m equivalents of fatty derivatives R'CO-AK'2 with m' greater than or equal to m, and m being as defined above, under conditions known to the person skilled in the art to form an ester bond Y according to the scheme below:

[0185] (H)pZ(0H)m+mR'C0-AK'2 -> (H)pZ(OH)m,m(YAK'2)m

[0186] diagram in which:

[0187] - Y represents -OC(O)- ;

[0188] - R' designating in particular -OH or -Cl; preferably R' designates -OH;

[0189] - AK'2 represents a linear or branched, unsaturated hydrocarbon chain, in Ci -C40, preferably in Ci4-C20, said chain being optionally interrupted by one or more heteroatoms or groups chosen from -O-, -S-, -C(O)-, (hetero)cycle(s), and their combinations, in particular -OC(O)-, -C(O)-O- or -(hetero)cycle-O-(hetero)cycle-, preferably interrupted by -O- or -S-, more preferably being uninterrupted.

[0190] According to a preferred embodiment, m is equal to m'.

[0191] Polyols (H)pZ(OH)m can be cyclic or acyclic.

[0192] Examples of (H)pZ(OH)mcyclic polyols include maltose, lactose, raffinose, sucrose, trehalose, melibiulose, melibiose, mannobiose, kojibiose, nigerose, isomaltose, rutinose, rutinulose, xylobiose or sorbitan.

[0193] Examples of (H)pZ(OH)macyclic polyols include ethylene glycol, propylene glycol, butylene glycol, pentylene glycol, hexylene glycol, butanediol, glycerol, pentaerythritol, dipentaerythritol, trimethylolethan, mannitol, or trimethylolpropane.

[0194] According to a preferred embodiment, the polyol (H)pZ(OH)m is chosen from glycerol, mannitol, sucrose, ethylene glycol, sorbitan, or trimethylolpropane, more preferably the polyol (H)pZ(OH)m designates glycerol.

[0195] The R'CO-AK'2 compounds are preferably unsaturated fatty acids of 15 to 36 carbon atoms, preferably of 15 to 24 carbon atoms. They may be monounsaturated or polyunsaturated.

[0196] Monounsaturated fatty acids are in particular selected from palmitoleic acid, oleic acid, 9-eicosenoic acid, 11-eicosenoic acid, erucic acid and nervonic acid.

[0197] Polyunsaturated fatty acids are selected in particular from linoleic acid, α-linolenic acid, γ-linolenic acid, dihomo-γ-linolenic acid, arachidonic acid, eicosapentaenoic acid, docosahexaenoic acid, ruminic acid, monounsaturated hydroxy fatty acids selected in particular from 10-Hydroxy-cis-12-octadecenoic acid, 10-Hydroxy-trans-11-octadecenoic acid, 12-Hydroxy-cis-9-octadecenoic acid, 13-Hydroxy-cis-9-octadecenoic acid, ricinoleic acid, isoricinoleic acid, and polyunsaturated hydroxy fatty acids selected in particular from densipolic acid, auricolic acid, dimorphecolic acid.

[0198] More preferably, the unsaturated fatty acid is chosen from ricinoleic acid, oleic acid, palmitoleic acid, erucic acid and mixtures thereof. Second stage

[0199] In a second step, all or part of the unsaturation(s) of the AK'2 radical(s) are transformed a) via an epoxidation reaction into epoxide to lead to derivatives (III), such as the starting compound al illustrated in the scheme described below, or b) via a thiol-ene reaction with a (poly)hydroxylated thiol or a thiol bearing acid function(s) to lead to derivatives (IV), such as, for example, compound b3 illustrated in the scheme described after.

[0200] The thiol-ene reaction b) can be carried out from (poly)hydroxylated thiols such as linear hydroxylated thiols of formula HS-(CH2)k-OH with k being a number whole from 1 to 12, preferably from 1 to 6, such as 2-mercaptoethanol, 3-mercapto-1-propanol, 6-mercapto-l-hexanol, 4-mercapto-l-butanol, or such as branched hydroxylated thiols preferably having from 1 to 6 carbon atoms, such as 3-mercapto-3-methylbutanol, 3-mercapto-2-butanol, or such as polyhydroxylated thiols, preferably having from 1 to 6 carbon atoms such as 3-mercapto-1,2 propanediol HS-CH(OH)-CH2OH.

[0201] The compounds (IV) obtained are thus substituted by a radical -S-AK3-(OH)V with v equal to 1 if the thiol is hydroxylated and v greater than 1, such as 2, if the thiol is polyhydroxylated, AK3 and v being such as defined previously for the compounds of formula (I). Third stage

[0202] In a third step, all or part of the epoxide groups of the compounds of formula (III) are opened by nucleophilic compounds, in particular i) alcohols preferably in Ci-C4 such as methanol or ethanol, or a polyol to lead to compounds (Illi), such as compound b2 illustrated in the diagram below, ii) carboxylic acids, preferably in Ci-C6, such as lactic acid, pyruvic acid, benzoic acid, glycolic acid or 2,2 bishydroxymethylpropionic acid, more preferably carboxylic acids substituted by at least one hydroxyl radical such as lactic acid, to lead to compounds (Illii), such as compound bl illustrated in the diagram below.

[0203] According to a preferred embodiment, the carboxylic acid ii) is chosen from lactic acid, glycolic acid or 2,2 bis hydroxymethyl propionic acid (epoxy-acid reaction) and the reaction is carried out in the presence of a catalyst such as imidazole, 1-Methylimidazole, N,N dimethylbenzylamine or caffeine.

[0204] According to a preferred embodiment, the alcohol i) is selected from ethylene glycol, propylene glycol, butylene glycol, pentylene glycol, hexylene glycol, butandiol, glycerol, pentaerythritol, dipentaerythritol, trimethylolethane, trimethylolpropane, more preferably butylene glycol or trimethylolethane. Fourth step

[0205] In a fourth step, all or part of the alcohol -OH functions of the compounds (Illi) or (Illii) and all or part of the alcohol functions possibly still present from the polyols (H)pZ(OH)m' used in the first step are transformed into -0-C(0)-C(Ra)(Rb)-C(0)-R4 radicals, for example via a (trans)esterification reaction with a Gp-C(0)-C(Ra)(Rb)-C(0)-R4 ester, in which Gp preferably designates a hydroxy radical or a (Ci-C4)alkoxy radical, such as methoxy, ethoxy, isobutoxy or t-butoxy.

[0206] According to a preferred embodiment, Gp-C(O)-C(Ra)(Rb)-C(O)-R4 designates an ester selected from ethyl acetoacetate, ethyl 2-methylacetoacetate, ter-butyl acetoacetate, preferably ter-butyl acetoacetate.

[0207] Structural compounds (la), (le), such as structural compounds (lie), structural compounds (Id) and (le) can be obtained according to this process.

[0208] By way of example, step 4 can be implemented according to the protocol described in Trevino, AS, & Trumbo, DL (2002). Acetoacetylated castor oil in coatings applications. Progress in Organic Coatings, 44(1), 49-54:

[0209] In some cases, the compounds (H)pZ(OH)m' m (YAK'2) produced in the first step are commercially available, in particular certain compounds for which m' equals m, p equals 0, and Z preferably denotes -CH2-CH-CH2-. When p equals 0 and m' equals m, the compounds are esters of unsaturated fatty acids, possibly hydroxylated, in particular triglycerides of castor oil, soybean oil, canola oil, or linseed oil. The synthesis of compounds (la) to (le) then begins from the second step described above.

[0210] For example, starting from an unsaturated triglyceride, a thiol-ene reaction is carried out with a (poly)hydroxy thiol such as SH-(CH2)X OH with x being an integer preferably from 1 to 4, then a transesterification reaction (as described in Desroches, M., Caillol, S., Lapinte, V., Auvergne, R., & Boutevin, B. (2011). Synthesis of biobased polyols by thiol-ene coupling from vegetable oils. Macromolecules, 44(8), 2489-2500: Compound b3

[0211] For example, starting from an unsaturated triglyceride, a total or partial epoxidation reaction is carried out, followed by the opening of the epoxide(s) formed, which generates alcohol functionalities and (trans)esterification. A commercial epoxidized triglyceride, such as the products offered by Arkema under the references Vikoflex 7170 or Vikoflex 7190, can also be used as a raw material.

[0212] By way of example, the reaction scheme below can be implemented in which all the epoxides are opened by lactic acid and then each hydroxyl group is esterified by t-Bu-OCOCH2CH3, according to the scheme below: has) Composed al Composed bi b) Compound b! Compound C1

[0213] As an example, the reaction scheme below can also be implemented in which all the epoxides are opened by an alcohol, methanol in the example, then each hydroxyl group is esterified by t-Bu-OCOCH2CH3: has) Compound a2 Compound 62 b) Compound b2 Coaxed c2

[0214] The compounds of formula (la) to (le) can further be prepared by the following series of reactions:

[0215] - In a first step, a commercial polyacid is reacted preferably natural (H)pZ(COOH)m with m equivalents of fatty alcohol HO-AK'2 with m' greater than or equal to m, and m being as defined above, under conditions known to a person skilled in the art to form an ester Y bond according to the scheme below:

[0216] (H)pZ(C00H)m +mH0-AK'2 -> (H)pZ(COOH)m _m(YAK'2)m

[0217] in which Y denotes -C(O)-O-, and AK'2 represents a linear or branched, unsaturated monovalent hydrocarbon chain, in Ci-C40, preferably in Ci4-C2o, said chain being optionally interrupted by one or more heteroatoms or groups chosen from -O-, -S-, -C(O)-, (hetero)cycle(s), and their combinations, in particular -OC(O)-, -C(O)-O-, -(hetero)cycle-O-(hetero)cycle-, preferably interrupted by -O- or -S-, and more preferably uninterrupted.

[0218] According to a preferred embodiment, m is equal to m'.

[0219] Polyacids (H)pZ(OH)m can be cyclic or acyclic.

[0220] Polyacids may preferably designate dicarboxylic acids possibly hydroxylated, tricarboxylic acids possibly hydroxylated, tetraboxylic acids possibly hydroxylated.

[0221] Non-hydroxylated dicarboxylic acids are selected in particular from maleic acid, propanedioic acid, butanedioic acid, pentanedioic acid, hexanedioic acid, decanedioic acid, dodecanedioic acid, cyclopropanedicarboxylic acid, cyclohexanedicarboxylic acid, cyclobutanedicarboxylic acid, naphthalene-1,4-dicarboxylic acid, naphthalene-2,3-dicarboxylic acid, naphthalene-2,6-dicarboxylic acid, suberic acid, oxalic acid, malonic acid, succinic acid, phthalic acid, terephthalic acid, isophthalic acid, tetrahydrophthalic acid, hexahydrophthalic acid, pimelic acid, sebacic acid, azelaic acid, acid glutaric acid, adipic acid, fumaric acid, itaconic acid, and preferably propanedioic acid, butanedioic acid and pentanedioic acid.

[0222] Hydroxylated dicarboxylic acids are in particular selected from tartaric acid, malic acid, aleuritic acid, 7,18-dihydroxy-tetracos-15-enoic acid, avenic acid B, and preferably malic acid and tartaric acid.

[0223] The (hydroxy) tricarboxylic acids are in particular selected from 2-oxaloglutaric acid, oxalosuccinic acid, 3-carboxymethyl muconic acid, 2-methyl citric acid, citric acid, isocitric acid, aconitic acid, transaconitic acid, 1,2,3-propanetricarboxylic acid, 1,2,5-pentanetricarboxylic acid, 1,3,5-benzenetricarboxylic acid, 1,3,5-cyclohexanetricarboxylic acid, 3-butene-1,2,3-tricarboxylic acid, 3-butene-1,1,3-tricarboxylic acid, trimellitic acid, 1,2,3-benzenetricarboxylic acid, 1,3,5-benzenetricarboxylic acid, agaric acid, preferably citric acid and acotinic acid.

[0224] Tetracarboxylic acids are in particular selected from 1,2,3,4-butanetetracarboxylic acid, pyromellitic acid, oxydisuccinic acid, thiodisuccinic acid, N[l,2-dicarboxyethyl]-L-aspartic acid, ethylenediamine tetraacetic acid, ethylenediamine tetrapropionic acid and N,N'-ethylene di-(L-aspartic acid).

[0225] According to a preferred embodiment, the fatty alcohols HO-AK'2 are selected from fatty alcohols comprising 15 to 36 carbon atoms, preferably 15 to 24 carbon atoms.

[0226] Fatty alcohols HO-AK'2 can be mono or polyunsaturated (presence of one or more ethylenic double bonds).

[0227] HO-AK'2 fatty alcohols may contain several alcohol functions.

[0228] Monounsaturated fatty alcohols are particularly chosen, oleyl alcohol, the Docosenol, unsaturated fatty alcohol ethers, such as polyoxyethylene monooleyl ether, preferably oleyl alcohol. Monounsaturated fatty alcohols containing multiple alcohol groups are particularly selected from 9-Octadecene-1,12-diol.

[0229] Polyunsaturated fatty alcohols are selected in particular from linoleic alcohol, 2,4-Dodecadien-l-ol, dolichols (with n being greater than or equal to 3, and less than or equal to 5).

[0230] According to a preferred embodiment, fatty alcohol HO-AK'2 is selected from oleyl alcohol, linoleyl alcohol or mixtures thereof.

[0231] The following steps are identical to those described previously:

[0232] - In a second step, all or part of the unsaturation(s) of the radical(s) AK'2 are transformed a) via an epoxidation reaction to epoxide to lead to (III') derivatives, such as compound a4 illustrated in the scheme below, or b) via a thiol-ene reaction with a (poly)hydroxylated thiol or a thiol bearing acid function(s) to lead to derivatives (IV'), such as compound b5 illustrated in the diagram below.

[0233] - In a third step, all or part of the epoxide groups of the compounds of formula (III') are opened by nucleophilic compounds, such as i) alcohols preferably in C1-C4 such as methanol or ethanol or a polyol to lead to compounds (III'i), such as compound b4 illustrated in the diagram below, ii) carboxylic acids preferably in Ci-C6 such as lactic acid, pyruvic acid, benzoic acid, more preferably carboxylic acids substituted by at least one hydroxyl radical such as lactic acid, to lead to compounds (III'ii), such as compound b6 illustrated in the diagram below.

[0234] - In a fourth step, all or part of the alcohol -OH functions of the compounds (Ill'i) or (Ill'ii) and all or part of the alcohol functions possibly still present and derived from the polyols (H)pZ(OH)m- implemented in the first step are transformed into -OC(O)-C(Ra)(Rb)-C(O)-R4 radicals, for example via a transesterification reaction with a Gp-C(O)-C(Ra)(Rb)-C(O)-R4 ester in which Gp preferably designates a hindered alkoxy radical such as tBu-O- to lead to the corresponding formula (I) compounds.

[0235] Compounds of formula (la) to (le) such that p equals 1, Y denotes -C(O)-O- and m equals 1 can also be prepared by combining steps 2, 3 and 4 described above, from an unsaturated fatty acid such as oleic acid as described in "The synthesis of Bio-based Michael donors from tall oil fatty acids for polymer development", Polymers, 2022,14, 4107.

[0236] By way of example, the reaction scheme below can be implemented in which all the epoxides are opened by methanol and then each hydroxyl group is esterified by t-Bu-OCOCH2CH3: A4 format Compound b4 Compound b4 Compound c4

[0237] By way of example, the reaction scheme below can be implemented in which an unsaturated oil reacts with a (poly)hydroxy thiol such as SH-(CH2)xOH, with x being an integer preferably from 1 to 4, followed by a transesterification reaction (as described in Desroches, M., Caillol, S., Lapinte, V., Auvergne, R., & Boutevin, B. (2011). Synthesis of biobased polyols by thiol-ene coupling from vegetable oils. Macromolecules, 44(8), 2489-2500): Compound b 5 Compound c5

[0238] By way of example, the reaction scheme below can be implemented in which all the epoxides are opened by lactic acid and then each hydroxyl group is esterified by t-Bu-OCOCH2CH3: Compound 36 Compound b6

[0239]

[0240]

[0241]

[0242]

[0243]

[0244]

[0245]

[0246] Compound b6 Compound e6 iii) Coloring agent According to the process of the invention, at least one coloring agent selected from pigments, direct dyes, and mixtures thereof is applied to the keratin fibers iii). Preferably, the coloring agent(s) are chosen from pigments. The term "pigment" refers to all pigments that impart color to keratinous materials. Their solubility in water at 25°C and atmospheric pressure (760 mmHg) is less than 0.05% by weight, and preferably less than 0.01% (in g / L of water). The pigments that can be used are chosen in particular from among the organic and / or mineral pigments known to the technique, especially those described in Kirk-Othmer's Encyclopedia of Chemical Technology and in Ullmann's Encyclopedia of Industrial Chemistry. They can be natural, of natural origin, or not. These pigments can be in powder or paste form. They can be coated or uncoated. Pigments can, for example, be chosen from mineral pigments, organic pigments, lacquers, special effect pigments such as mother-of-pearl or glitter, and mixtures thereof. The pigment can be a mineral pigment. By mineral pigment, we mean any pigment that meets the definition in the Ullmann encyclopedia, in the chapter on inorganic pigments. Among the mineral pigments useful in this context, we can cite... invention, iron or chromium oxides, manganese violet, ultramarine blue, chromium hydrate, ferric blue and titanium oxide.

[0247] The pigment may be an organic pigment. By "organic pigment" is meant any pigment that meets the definition in the Ullmann encyclopedia in the chapter on organic pigment.

[0248] The organic pigment may in particular be selected from the following compounds: nitroso, nitro, azo, xanthene, pyrene, quinoline, quinoline, anthraquinone, triphenylmethane, fluorane, phthalocyanine, metal complex type, isoindolinone, isoindoline, quinacridone, perinone, perylene, diketopyrrolopyrrole, indigo, thioindigo, dioxazine, triphenylmethane, quinophthalone.

[0249] In particular, white or colored organic pigments may be selected from carmine, carbon black, aniline black, azo yellow, quinacridone, phthalocyanine blue, the blue pigments coded in the Color Index under references Cl 42090, 69800, 69825, 74100, 74160, the yellow pigments coded in the Color Index under references Cl 11680, 11710, 19140, 20040, 21100, 21108, 47000, 47005, the green pigments coded in the Color Index under references Cl 61565, 61570, 74260, the orange pigments coded in the Color Index under reference CI 11725, 45370, 71105, the red pigments coded in the Color Index under the references CI 12085, 12120, 12370, 12420, 12490, 14700, 15525, 15580, 15620, 15630, 15800, 15850, 15865, 15880, 26100, 45380, 45410, 58000, 73360, 73915, 75470, the pigments obtained by oxidative polymerization of indole, phenolic derivatives as described in patent FR 2 679 771.

[0250] By way of example, one can also cite organic pigment pastes such as the products sold by the company HOECHST under the name:

[0251] - COSMENYL YELLOW IOG: Pigment YELLOW 3 (Cl 11710);

[0252] - COSMENYL YELLOW G: Pigment YELLOW 1 (Cl 11680);

[0253] - ORANGE COSMENYL GR: Pigment ORANGE 43 (Cl 71105);

[0254] - COSMENYL RED R: Pigment RED 4 (Cl 12085);

[0255] - CARMIN COSMENYL FB: Pigment RED 5 (Cl 12490);

[0256] - VIOLET COSMENYL RL: Pigment VIOLET 23 (Cl 51319);

[0257] - COSMENYL BLUE A2R: Pigment BLUE 15.1 (Cl 74160);

[0258] - COSMENYL GREEN GG: Pigment GREEN 7 (Cl 74260);

[0259] - COSMENYL BLACK R: Pigment BLACK 7 (Cl 77266).

[0260] The pigments according to the invention can also be in the form of composite pigments as described in patent EP 1 184 426. These composite pigments can be composed in particular of particles comprising an inorganic core, at least one binder ensuring the fixation of organic pigments on the core, and at least one organic pigment covering at least partially the core.

[0261] The organic pigment can also be a lake. By lake, we mean colorants adsorbed onto insoluble particles, the whole thus obtained remaining insoluble during use.

[0262] The inorganic substrates on which the dyes are adsorbed are, for example, alumina, silica, calcium sodium borosilicate or calcium aluminium borosilicate, and aluminium.

[0263] Among the colorants, we can mention carminic acid. We can also mention the colorants known under the following names: D & C Red 21 (CI 45 380), D & C Orange 5 (CI 45 370), D & C Red 27 (CI 45 410), D & C Orange 10 (CI 45 425), D & C Red 3 (CI 45 430), D & C Red 4 (CI 15 510), D & C Red 33 (CI 17 200), D & C Yellow 5 (CI 19 140), D & C Yellow 6 (CI 15 985), D & C Green (CI 61 570), D & C Yellow 1 O (CI 77 002), D & C Green 3 (CI 42 053), D & C Blue 1 (CI 42 090).

[0264] As examples of lacquers, we can cite the product known under the following name: D & C Red 7 (CI 15 850 :1).

[0265] The pigment can also be a special effects pigment. Special effects pigments are defined as pigments that generally create a non-uniform and changing colored appearance (characterized by a certain shade, vibrancy, and clarity) depending on the viewing conditions (light, temperature, viewing angles, etc.). They are thus distinct from colored pigments that provide a uniform opaque, semi-transparent, or conventionally transparent tint.

[0266] There are several types of special effect pigments, those with a low refractive index such as fluorescent or photochromic pigments, and those with a higher refractive index such as mother-of-pearl, interference pigments or glitter.

[0267] Examples of special effect pigments include pearlescent pigments such as titanium-coated mica or bismuth oxychloride, colored pearlescent pigments such as titanium-coated mica with iron oxides, iron oxide-coated mica, titanium-coated mica, particularly with ferric blue or chromium oxide, titanium-coated mica with an organic pigment as defined above, and bismuth oxychloride-based pearlescent pigments. Examples of pearlescent pigments include Cellini pearlescent pigments marketed by BASF (Mica-TiO2-lacquer), Prestige pearlescent pigments marketed by Eckart (Mica-TiO2), Prestige Bronze pearlescent pigments marketed by Eckart (Mica-Fe2O3), and Colorona pearlescent pigments marketed by Merck (Mica-TiO2-Fe2O3).

[0268] We can also mention gold-colored mother-of-pearl, notably marketed by BASF under the names Brilliant Gold 212G (Timica), Gold 222C (Cloisonne), Sparkle Gold (Timica), Gold 4504 (Chromalite) and Monarch Gold 233X (Cloisonne); bronze mother-of-pearl, notably marketed by MERCK under the designation Bronze fine (17384) (Colorona) and Bronze (17353) (Colorona) and by the company BASF under the name Super bronze (Cloisonne); the orange mother-of-pearls notably marketed by the company BASF under the name Orange 363C (Cloisonne) and Orange MCR 101 (Cosmica) and by the company MERCK under the name Passion orange (Colorona) and Matte orange (17449) (Microna); Brown mother-of-pearl, notably marketed by BASF under the names Nu-antique Copper 340XB (Cloisonne) and Brown CL4509 (Chromalite); copper-tinted mother-of-pearl, notably marketed by BASF under the name Copper 340A (Timica); red-tinted mother-of-pearl, notably marketed by MERCK under the name Sienna Fine (17386) (Colorona); yellow-tinted mother-of-pearl, notably marketed by BASF under the name Yellow (4502) (Chromalite); red mother-of-pearl with a gold tint, notably marketed by BASF under the name Sunstone G012 (Gemtone); pink mother-of-pearl, notably marketed by BASF under the name Tan opale G005 (Gemtone);black mother-of-pearl with a gold sheen, notably marketed by BASF under the name Nu antique bronze 240 AB (Timica), blue mother-of-pearl, notably marketed by MERCK under the name Matte Blue (17433) (Microna), white mother-of-pearl with a silver sheen, notably marketed by MERCK under the name Xirona Silver, and orange-pink-green-gold mother-of-pearl, notably marketed by MERCK under the name Indian Summer (Xirona), and their mixtures.

[0269] As further examples of nacres, we can also mention particles comprising a borosilicate substrate coated with titanium oxide.

[0270] Particles with a glass substrate coated with titanium oxide are notably sold under the name METASHINE MC1080RY by the company TOYAL.

[0271] Finally, examples of mother-of-pearl include polyethylene terephthalate flakes, particularly those marketed by Meadowbrook Inventions under the name Silver IP 0.004X0.004 (silver flakes). Multilayer pigments based on synthetic substrates such as alumina, silica, calcium sodium borosilicate or calcium aluminum borosilicate, and aluminum can also be considered.

[0272] Special effect pigments may also be selected from reflective particles, that is to say, in particular, particles whose size, structure, including the thickness of the layer(s) constituting them and their physical and chemical nature, and surface condition, enable them to reflect incident light. This reflection may, where appropriate, have sufficient intensity to create a surface effect on the composition or mixture when it is applied to the substrate. In makeup, highlights are visible to the naked eye, that is, brighter points that contrast with their surroundings by appearing to shine.

[0273] Reflective particles can be selected so as not to significantly alter the coloring effect generated by the coloring agents associated with them, and more particularly so as to optimize this effect in terms of color rendering. They may, in particular, have a yellow, pink, red, bronze, orange, brown, gold and / or copper color or reflection.

[0274] These particles can have various shapes, including being platelet-shaped or globular, particularly spherical.

[0275] Reflective particles, whatever their shape, may or may not have a multilayer structure and, in the case of a multilayer structure, for example at least one layer of uniform thickness, in particular of a reflective material.

[0276] When reflective particles do not have a multilayer structure, they can be composed, for example, of metal oxides, in particular titanium or iron oxides obtained by synthesis.

[0277] When reflective particles have a multilayer structure, they may, for example, comprise a natural or synthetic substrate, in particular a synthetic substrate at least partially coated by at least one layer of a reflective material, in particular at least one metal or metallic material. The substrate may be monomaterial, multimaterial, organic and / or inorganic.

[0278] More specifically, it may be selected from glasses, ceramics, graphite, metal oxides, aluminas, silicas, silicates, in particular aluminosilicates and borosilicates, synthetic mica and mixtures thereof, this list not being exhaustive.

[0279] The reflective material may include a layer of metal or a metallic material.

[0280] Reflective particles are described in particular in documents JP-A-09188830, JP-A-10158450, JP-A-10158541, JP-A-07258460 and JP-A-05017710.

[0281] As further examples of reflective particles comprising a mineral substrate coated with a layer of metal, one can also mention particles comprising a borosilicate substrate coated with silver.

[0282] Silver-coated glass substrate particles in the form of wafers are sold under the name MICROGLASS METASHINE REFSX 2025 PS by the company TOYAL. Nickel / chromium / molybdenum alloy-coated glass substrate particles are sold under the names CRYSTAL STAR GF 550, GF 2525 by the same company.

[0283] Particles comprising a metallic substrate such as silver, aluminum, iron, chromium, nickel, molybdenum, gold, copper, can also be used. zinc, tin, magnesium, steel, bronze, titanium, said substrate being coated with at least one layer of at least one metal oxide such as titanium oxide, aluminium oxide, iron oxide, cerium oxide, chromium oxide, silicon oxides and mixtures thereof.

[0284] An example can be cited as aluminium, bronze or copper powders coated with SiO2 marketed under the name VISIONAIRE by the company ECKART.

[0285] Other examples include non-substrate interference pigments such as liquid crystals (Wacker's Helicones HC) and interference holographic glitter (Spectratek's Geometry Pigments or Spectra f / x). Special effect pigments also include fluorescent pigments, whether daylight fluorescent or ultraviolet fluorescent, phosphorescent pigments, photochromic pigments, thermochromic pigments, and quantum dots, marketed, for example, by Quantum Dots Corporation.

[0286] The variety of pigments that can be used in the present invention makes it possible to obtain a rich palette of colors, as well as particular optical effects such as metallic, interference effects.

[0287] The size of the pigment used in the composition according to the present invention is generally between 10 nm and 200 µm, preferably between 20 nm and 80 µm, and more preferably between 30 nm and 50 µm.

[0288] The pigments can be dispersed within the composition by means of a dispersing agent.

[0289] The dispersing agent serves to protect the dispersed particles from agglomeration or flocculation. This dispersing agent may be a surfactant, an oligomer, a polymer, or a mixture of several of these, possessing one or more functionalities with a strong affinity for the surface of the particles to be dispersed. In particular, they may adhere physically or chemically to the surface of the pigments. These dispersants also have at least one functional group that is compatible with or soluble in the continuous medium.In particular, esters of 12-hydroxystearic acid are used, especially C8 to C20 fatty acids and polyols such as glycerol, diglycerin, such as poly(12-hydroxystearic acid) stearate with a molecular weight of approximately 750g / mol such as that sold under the name Solsperse 21 000 by Avecia, polyglyceryl-2 dipolyhydroxystearate (name CTFA) sold under the reference Dehymyls PGPH by Henkel or polyhydroxystearic acid such as that sold under the reference Arlacel P100 by Uniqema and their mixtures.

[0290] As another dispersant that can be used in the compositions of the invention, mention may be made of quaternary ammonium derivatives of polycondensed fatty acids such as Solsperse 17000 sold by Avecia, and polydimethylsiloxane / oxypropylene mixtures such as those sold by Dow Corning under the references DC2-5185, DC2-5225 C.

[0291] The pigments used in the invention can be surface treated with an organic agent.

[0292] Thus, the pigments previously surface-treated useful within the framework of the invention are pigments which have undergone totally or partially a surface treatment of a chemical, electronic, electro-chemical, mechano-chemical or mechanical nature, with an organic agent such as those described in particular in Cosmetics and Toiletries, February 1990, Vol. 105, pp. 53-64 before being dispersed in the composition according to the invention.These organic agents may be chosen, for example, from waxes, such as carnauba wax and beeswax; fatty acids, fatty alcohols and their derivatives, such as stearic acid, hydroxystearic acid, stearyl alcohol, hydroxystearyl alcohol, lauric acid and their derivatives; anionic surfactants; lecithins; sodium, potassium, magnesium, iron, titanium, zinc or aluminum salts of fatty acids, for example aluminum stearate or laurate; metal alkoxides; polyethylene; (meth)acrylic polymers, for example polymethyl methacrylates; polymers and copolymers containing acrylate units; alkanoamines; silicone compounds, for example silicones, in particular polydimethylsiloxanes; fluorinated organic compounds, for example perfluoroalkyl ethers; Fluoro-silicon compounds.

[0293] The surface-treated pigments useful in the invention may also have been treated by a mixture of these compounds and / or have undergone several surface treatments.

[0294] The surface-treated pigments useful in the context of the present invention can be prepared using surface treatment techniques well known to those skilled in the art or found as such in the commercial market.

[0295] Preferably, the surface-treated pigments are covered by an organic layer.

[0296] The organic agent with which the pigments are treated can be deposited on the pigments by solvent evaporation, chemical reaction between the molecules of the surfactant or creation of a covalent bond between the surfactant and the pigments.

[0297] Surface treatment can thus be achieved, for example, by a chemical reaction of a surfactant with the surface of the pigments and the creation of a covalent bond between the surfactant and the pigments or fillers. This method is described in particular in US patent 4,578,266.

[0298] Preferably, an organic agent covalently linked to the pigments will be used.

[0299] The surface treatment agent may represent from 0.1 to 50% by weight of the total weight of the pigment treated on the surface, preferably from 0.5 to 30% by weight, and even more preferably from 1 to 20% by weight of the total weight of the pigment treated on the surface.

[0300] Preferably, the surface treatments of the pigments are chosen from the following treatments:

[0301] - a PEG-Silicone treatment such as the AQ surface treatment marketed by LCW;

[0302] - a Methicone treatment such as the SI surface treatment marketed by LCW;

[0303] - a Dimethicone treatment such as the Covasil 3.05 surface treatment marketed by LCW;

[0304] - a Dimethicone / Trimethylsiloxysilicate treatment as the surface treatment Covasil 4.05 marketed by LCW;

[0305] - a Magnesium Myristate treatment such as MM surface treatment marketed by LCW;

[0306] - an Aluminium Dimyristate treatment such as the MI surface treatment marketed by Miyoshi;

[0307] - a Perfluoropolymethylisopropyl ether treatment as a surface treatment FHC marketed by LCW;

[0308] - an Isostearyl Sebacate treatment such as the commercially available HS surface treatment by Miyoshi;

[0309] - a Perfluoroalkyl Phosphate treatment as a PF surface treatment marketed by Daito;

[0310] - an acrylate / dimethicone copolymer and perfluoalkyl phosphate treatment such as the FSA surface treatment marketed by Daito;

[0311] - a Polymethylhydrogen siloxane / Perfluoroalkyl Phosphate treatment such as the FS01 surface treatment marketed by Daito;

[0312] - an Acrylate / Dimethicone Copolymer treatment as the surface treatment ASC marketed by Daito;

[0313] - an Isopropyl Titanium Triisostearate treatment such as the ITT surface treatment marketed by Daito;

[0314] - an Acrylate copolymer treatment such as the APD surface treatment marketed by Daito;

[0315] - a Perfluoroalkyl Phosphate / Isopropyl Titanium Triisostearate treatment such as the PF + ITT surface treatment marketed by Daito.

[0316] Preferably, the dispersing agent is present with organic or inorganic pigments in submicron-sized particulate form.

[0317] By "sub-micronic" or in English "sub-micronic" is meant pigments whose particle size has been micronized by micronization method and whose average particle size is less than one micrometer (pm), in particular between 0.1 and 0.9 pm, and preferably between 0.2 and 0.6 pm.

[0318] Preferably, the dispersing agent and the pigment(s) are present in quantity (dispersing agent: pigment), according to a weight ratio, between 1:4 and 4:1, particularly between 1.5:3.5 and 3.5:1 or better between 1.75:3 and 3:1.

[0319] The dispersing agent(s) may therefore have a silicone skeleton, such as silicone polyether and amino-silicone dispersants. Suitable dispersing agents include:

[0320] - amino-silicones i.e. silicones comprising one or more amino groups such than those marketed under the names and references: BYK LPX 21879, by BYK, GP-4, GP-6, GP-344, GP-851, GP-965, GP-967 and GP-988-1, marketed by Genesee Polymers,

[0321] - silicone acrylates such as Tego ® RC 902, Tego ® RC 922, Tego ® RC 1041, and Tego ® RC 1043, marketed by Evonik,

[0322] - polydimethylsiloxane (PDMS) silicones with carboxylic groups such as X- 22162 and X-22370 by Shin-Etsu, silicone epoxy such as GP-29, GP-32, GP-502, GP-504, GP-514, GP-607, GP-682, and GP-695, by Genesee Polymers, or Tego ® RC 1401, Tego ® RC 1403, Tego ® RC 1412, by Evonik.

[0323] Preferably, the dispersing agent(s) are of the amino-silicone type and are cationic.

[0324] Preferably, the pigment(s) is / are chosen from mineral, mixed mineral-organic or organic pigments.

[0325] In one embodiment of the invention, the pigment(s) are organic pigments, preferably organic pigments surface-treated with an organic agent selected from silicone compounds. In another embodiment of the invention, the pigment(s) are mineral pigments.

[0326] Preferably, the pigment(s) are chosen from zirconium oxides, zinc oxides, cerium oxides, iron oxides, titanium oxides, chromium oxides, manganese violet, ultramarine blue, ultramarine pink, chromium hydrate and ferric blue, and mixtures thereof; more preferably from titanium oxides such as titanium dioxide, iron oxides, chromium oxides in particular green chromium oxide, and mixtures thereof.

[0327] Even more preferably, the pigment(s) are chosen from iron oxides, in particular red, brown or black, especially red. Direct dyes

[0328] By "direct dye," we mean natural and / or synthetic dyes, different from oxidation dyes. These are dyes that diffuse superficially onto the fiber. They can be ionic, for example cationic or anionic, or non-ionic.

[0329] Examples of suitable direct dyes that may be mentioned include azo direct dyes; (poly)methine dyes such as cyanines, hemicyanines and styryls; carbonyl dyes; azine dyes; nitro(hetero)aryl dyes; tri(hetero)arylmethane dyes; porphyrin dyes; phthalocyanine dyes and natural direct dyes, alone or in mixtures.

[0330] Direct dyes can be selected from anionic direct dyes. The anionic direct dyes of the invention are dyes commonly called "acid" direct dyes because of their affinity for alkali substances. Anionic direct dyes are understood to mean any direct dye having in its structure at least one CO2R or SO3R substituent, where R designates a hydrogen atom or a cation from a metal or an amine, or an ammonium ion. Anionic dyes can be selected from acidic nitro direct dyes, acidic azo dyes, acidic azinic dyes, acidic triarylmethanic dyes, acidic indoamine dyes, acidic anthraquinone dyes, indigoids, and acidic natural dyes.

[0331] A titre d’exemple de colorants acides on peut citer : Acid Red 1, Acid Red 4, Acid Red 13, Acid Red 14, Acid Red 18, Acid Red 27, Acid Red 28, Acid Red 32, Acid Red 33, Acid Red 35, Acid Red 37, Acid Red 40, Acid Red 41, Acid Red 42, Acid Red 44, Pigment red 57, Acid Red 68, Acid Red 73, Acid Red 135, Acid Red 138, Acid Red 184, Food Red 1, Food Red 13, Acid Orange 6, Acid Orange 7, Acid Orange 10, Acid Orange 19, Acid Orange 20, Acid Orange 24, Yellow 6, Acid Yellow 9, Acid Yellow 36, Acid Yellow 199, Food Yellow 3; Acid Violet 7, Acid Violet 14, Acid Blue 113, Acid Blue 117, Acid Black 1, Acid Brown 4, Acid Brown 20, Acid Black 26, Acid Black 52, Food Black 1, Food Black 2 ; Food yellow 3 ou sunset yellow; Acid Red 111, Acid Red 134, Acid yellow 38 ;

[0332] A titre d’exemple de colorants azo anioniques pyrazolones on peut citer : Acid Red 195, Acid Yellow 23, Acid Yellow 27, Acid Yellow 76Acid Yellow 17 ;

[0333] As an example of anthraquinone dyes, we can cite: Acid Blue 25, Acid Blue 43, Acid Blue 62, Acid Blue 78, Acid Blue 129, Acid Blue 138, Acid Blue 140, Acid Blue 251, Acid Green 25, Acid Green 41, Acid Violet 42, Acid Violet 43, Mordant Red 3; EXT violet No. 2 Acid Black 48;

[0334] Examples of nitrated dyes include: Acid Brown 13; Acid Orange 3; examples of dyes of formula (XXII') include: Acid Yellow 1, Salt sodium 2,4-dinitro-l-naphthol-7-sulfonic acid, 2-piperidino-5-nitrobenzenesulfonic acid, 2(4'-N,N(2'-hydroxyethyl)amino-2'-nitro)aniline ethanesulfonic acid, 4-[3-hydroxyethylamino-3-nitrobenzenesulfonic acid; EXT D&C yellow 7;

[0335] Examples of triarylmethane dyes include: Acid Blue 1; Acid Blue 3; Acid Blue 7, Acid Blue 9; Acid Violet 49; Acid green 3; Acid green 5; Acid Green 50.

[0336] Examples of xanthenic dyes include: Acid Yellow 73; Acid Red 51; Acid Red 52, Acid Red 87; Acid Red 92; Acid Red 95; Acid Violet 9.

[0337] As an example of indole dyes, we can cite: Acid Blue 74;

[0338] Examples of quinoline dyes include: Acid Yellow 2, Acid Yellow 3 and Acid Yellow 5.

[0339] Among the natural direct dyes that can be used according to the invention are lawsone, juglone, alizarin, purpurin, carminic acid, kermesic acid, purpurogallin, protocatechaldehyde, indigo, isatin, curcumin, spinulosin, apigenidine, and orceins. Extracts or decoctions containing these natural dyes, and in particular henna-based poultices or extracts, can also be used.

[0340] Preferably, the total content of colouring agent(s) in a composition is in the range of 0.001% to 20% by weight, more preferably 0.005% to 15% by weight, relative to the total weight of the composition comprising it / them.

[0341] Preferably, the total pigment content in a composition is within the range of 0.05% to 20% by weight, more preferably from 0.1% to 15% by weight, better from 0.5% to 10% by weight, relative to the total weight of the composition comprising it / them.

[0342] Advantageously, the total content of direct colorant(s) in a composition is in the range of 0.001% to 10% by weight, more preferably 0.005% to 5% by weight, relative to the total weight of the composition comprising it / them. Additional (poly)amine compound iv)

[0343] Preferably, the process of the invention may further include the application to the keratin fibers of at least one additional (poly)amine compound iv).

[0344] The additional (poly)amine compounds iv) of the invention are different from the chitosan compounds i), the compounds ii) of formula (I) and the coloring agents iii) previously described.

[0345] The additional (poly)amine compound(s) iv) may in particular be selected from monoamine compounds, polyamine compounds having several primary and / or secondary amine groups, or from amino alkoxysilanes, and more particularly from amino alkoxysilane compounds, the compounds polyamines such as chitosans other than chitosan compounds i) or polylysines, diaminic compounds, triamine compounds, and mixtures thereof.

[0346] The additional (poly)amine compound(s) iv) may be a compound comprising from 2 to 20 carbon atoms, in particular a non-polymeric compound, it may be acyclic, or cyclic, linear or branched, 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 their combinations such as -Si(R')2-O- or -O-Si(R')2-, with R' identical or different, represents a (Ci-C4)alkyl group such as methyl, and R” represents a hydrogen atom or a (Ci-C4)alkyl group, preferably hydrogen.

[0347] By "non-polymer compound" is meant a compound that is not directly obtained by a polymerization reaction of monomers.

[0348] As additional (poly)amine compounds (iv), particular examples 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, methyl bis(3-aminopropyl)amine, N-(3-aminopropyl)-1,4-diaminobutane, N,N-dimethyldipropylene triamine, 1,2-bis(3-aminopropylamino)ethane, N,N'-bis(3-aminopropyl)-1,3-propanediamine, ethylenediamine, 1,3-propylenediamine, 1,4-butylenediamine, lysine, polylysine, cystamine, xylenediamine, tris(2-aminoethyl)amine, l,3-bis(aminomethyl)cyclohexane, l,4-bis(aminomethyl)cyclohexane, diaminopropanol such as l,3-diamino-2-propane-l ol, 4,7,10-Trioxa-l,13-tridecanediamine, spermidine, lysinol and C36-alkylenediamines (respectively Priamine™ 1071, 1073, 1074, 1075 marketed by CRODA), preferably 1,3-diamino-2-propane-l-ol, polylysine, spermidine, and mixtures thereof.

[0349] The (poly)amine compound(s) iv) may be monoamine i.e. contain a single primary and / or secondary amine group, preferably primary (NH2).

[0350] The (poly)amine compound(s) iv) may be triamine, i.e., contain three primary and / or secondary amine groups. Spermidine is an example of a triamine compound.

[0351] The (poly)amine compound(s) iv) may be polyamines, i.e., contain more than two primary and / or secondary amine groups, preferably primary (NH2). Polylysine is an example of a (poly)amine compound.

[0352] The additional (poly)amine compound(s) iv) may be selected from amino alkoxysilanes, in particular those of formula R'iSi(OR'2)z(R'3)x, in which:

[0353] - R' i is a linear or branched, saturated Ci-C6 hydrocarbon chain or unsaturated, cyclic or acyclic substituted by a group chosen from the primary amine group NH2 or secondary amine group -N(H)R with R representing a C1-C4 alkyl, aryl, or benzyl substituted by an amino group or by an aminoalkyl group in C1-C4; R can be interrupted in its chain by a heteroatom (O, S, NH) or a carbonyl group C(O), R being linked to the silicon atom directly via a carbon atom,

[0354] - R'2 and R'3, whether identical or different, represent a linear (Ci-C6)alkyl group or branched,

[0355] - z denotes an integer from 1 to 3, and

[0356] - x denotes an integer from 0 to 2,

[0357] with z + x = 3.

[0358] In particular, R'1 is an acyclic chain. Preferably, R'1 is a linear or branched, saturated or unsaturated C1-C6 hydrocarbon chain substituted with an amine group -NH2 or -N(H)R, where R represents a C1-C6 alkyl, a C3-C6 cycloalkyl, or a C6 aromatic. More preferably, R'1 is a linear saturated C1-C6 hydrocarbon chain substituted with an amine group NH2. Even more preferably, R'1 is a linear saturated C2-C4 hydrocarbon chain substituted with an amine group NH2.

[0359] In particular, R'2 represents an alkyl group comprising 1 to 4 carbon atoms, preferably R'2 represents a linear alkyl group comprising 1 to 4 carbon atoms, and more preferably R'2 represents the ethyl group.

[0360] In particular, R'3 represents an alkyl group comprising from 1 to 4 carbon atoms, preferably, R'3 represents a linear alkyl group comprising from 1 to 4 carbon atoms, and more preferably R'3 represents the methyl or ethyl group. Preferably, z is equal to 3.

[0361] In particular, the additional (poly)amine compound(s) iv) may be selected from amino alkoxysilanes having only one primary and / or secondary amine group, preferably primary (NH2) such as 3-aminopropyltrieth oxysilane (APTES), 3-aminoethyltriethoxysilane (AETES), 3-aminopropylmethyl diethoxysilane, N-(2-aminoethyl)-3-aminopropyltriethoxysilane, 3-(m-aminophenoxy)propyltrimethoxy-silane, p-aminophenyltrimethoxysilane, and N-(2-aminoethylaminomethyl)-phenethyltrimethoxysilane.

[0362] The (poly)amine compound(s) iv) may be selected from 3-aminopropyltriethoxysilane (APTES), 3-aminoethyltriethoxysilane (AETES), 3-aminopropylmethyldiethoxysilane, and N-(2-aminoethyl)-3-aminopropyltrieth oxysilane, and more preferably 3-aminopropyl triethoxysilane (APTES) or its oligomers.

[0363] The (poly)amine compound(s) iv) may be monoamine and may be chosen from polydialkylsiloxanes in particular of formula (IV) H2N-ALK-Si(R'2)(R'3)-O-[ Si(R'2)(R'3)-O]n- Si(R'2)(R'3)-R'4(IV)

[0364] Formula (IV) wherein ALK represents a (Ci-C4)alkylene group, linear or branched, preferably linear such as propylene, R'2 and R'3, identical or different, preferably identical, represent a (Ci-C4)alkyl group such as methyl, and R'4 represents a (Ci-C6)alkyl group, linear or branched, preferably at C4 such as n-butyl, 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.mol1. Examples of polydimethylsiloxanes (IV) include those sold under the names "MCR-A11" and "MCR-A12" by the company Gelest.

[0365] The (poly)amine compound(s) iv) may be diaminated, i.e., may contain two primary and / or secondary amine groups, preferably primary (NH2). More particularly, they may be selected from compounds of formulas (V) and (VI):

[0366] ALK[(O-ALK')m-NH2]2 (V) or

[0367] H2N-ALK-Si(R')2-[O-Si(R')2]mO-Si(R)2-ALK'-NH2 (VI)

[0368] formulas (V) and (VI) wherein ALK and ALK', identical or different, represent a (Ci-C6)alkylene group, linear or branched, preferably linear such as propyl, R', identical or different, represents a (CrC4)alkyl group such as methyl, m being 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.mol1 to 55000 g.mol1. Examples of compounds of formula (VI) include those sold under the names "DMS-A11", "DMS-A12", "DMS-A15", "DMS-A21", "DMS-A31", "DMS-A32" and "DMS-A35" by the company Gelest.

[0369] The additional (poly)amine compound(s) iv) which are diaminized are particularly chosen from diaminized polyethers in particular of formula H2N-ALK-O-[ALK'-O]m-ALK”-NH2 with ALK, ALK' and ALK”, identical or different representing a (Ci-C6)alkylene group, linear or branched, and m representing an integer greater than or equal to 0, such as 4,7,10-trioxa-l,13-tridecanediamine or compounds; in particular known under the reference Jeffamine from the Huntsman company; and more specifically polyethylene glycol and / or polypropylene glycol a, co-diamine (with amine function at the end of the chain) such as those sold under the names Jeffamine D-230, D-400, D-2000, D-4000, ED-600, ED-9000, ED-2003.

[0370] The (poly)amine compound(s) iv) may be triamined i.e. may contain three primary and / or secondary amine groups, preferably primary (NH2). In particular, triamine polyethers can notably have the formula ALK'”[(O-ALK')m-NH2]3 with ALK' as defined previously, ALK'” representing a trivalent (Ci-C6)alkylene group, linear or branched, and m represents an integer greater than or equal to 0.

[0371] As additional (poly)amine compounds iv) which are triamine, triamine polyethers, known under the reference Jeffamine from the Huntsman company, are particularly cited; and in particular polyethylene glycol and / or polypropylene glycol a, co-triamine (with amine function at the end of the chain) such as those sold under the names Jeffamine T-403.

[0372] As additional (poly)amine compounds iv) which are triamines, triamine polyethers are particularly cited, and in particular polyethylene glycol and / or polypropylene glycol a, co-triamine (with amine function at the end of the chain) such as those sold under the names Jeffamine T-403.

[0373] The additional (poly)amine compound(s) iv) may comprise more than three primary and / or secondary amine groups, preferably primary (NH2).

[0374] When the additional (poly)amine compound(s) iv) have more than three primary and / or secondary amine groups, they may be selected from poly(meth)acrylates or poly(meth)acrylamides bearing primary or secondary lateral amine functions, such as poly(3-aminopropyl)methacrylamide, poly(2-aminoethyl) methacrylate.

[0375] In addition, the additional polyamine compounds iv) may be selected from polydimethylsiloxanes comprising primary amine groups at the end of the chain and / or on side chains.

[0376] When the additional (poly)amine compound(s) iv) are selected from polydimethylsiloxanes comprising primary amine groups at the end of the chain and / or on side chains, they may in particular be selected from amino poly(alkylene (C2-C5)imines), and preferably polyethyleneimines and polypropyleneimines, in particular poly(ethyleneimine), in particular that sold under reference 408700 by Aldrich Chemical or under the trade name Lupasol by BASF, in particular with a molecular weight between 1,200 and 25,000 g.mol1; poly(allylamine), in particular that sold under reference 479136 by Aldrich Chemical; polyvinylamines and their copolymers, in particular with vinylamides, in particular vinylamine / vinylformamide copolymers such as those marketed under the name Lupamin® 9030 by BASF; polyamino acids with NH2 groups such as polylysine, in particular that sold by JNC Corporation (formerly Chisso); amino dextran, in particular that sold by the company. CarboMer Inc; polyvinyl amino alcohol, in particular that sold by CarboMer Inc, acrylamido(Ci-C6)alkylamine-based copolymers, in particular acrylamidopropylamine-based copolymers.

[0377] Polydimethylsiloxanes comprising primary amine groups at the end of the chain and / or on side chains may be selected from the following formulas (VII):

[0378] Ra-Si(Rb)(Rc)-O-[Si(Rb)(Rc)-O]m-[Si(ALK1-NH2)(Ra)-O]n-Si(Rb)(Rc)-Ra(VII)

[0379] formula (VII) wherein Ra, identical or different, represents a hydroxy or (Ci-C4)alkyl group, Rb and Rc, identical or different, preferably identical, represent a (Ci-C4)alkyl group such as methyl, ALK1 represents a (Ci-C6)alkylene group, linear or branched, optionally interrupted by an N(H) group, m and n are integers greater than or equal to 1, preferably m and n are such that the weight-average molecular mass of the compound of formula (VII) ranges from 1000 g.mol1 to 500000 g.mol1.

[0380] Preferably, formula (VII) is such that Ra, Rb, and Rc represent a methyl group, ALK1 represents a propylene group, and the values ​​of n and m are such that the weight-average molecular weight of the polydimethylsiloxane ranges from 1000 g.mol1 to 55000 g.mol1. Examples of polydimethylsiloxanes of formula (VI) include those sold under the names "AMS-132", "AMS-152", "AMS-162", "AMS-163", "AMS-191", and "AMS-1203" by the company Gelest.

[0381] Advantageously, formula (VII) is such that Ra represents a hydroxyl or (Ci-C4)alkyl group such as methyl, ALK1 represents a (C5-C6)alkylene group substituted by an NH group, preferably ALK1 represents -(CH2)3-N(H)-(CH2)2-, and m and n are such that the weight average molecular mass of the compound of formula (VI) ranges from 5000 g.mol1 to 500000 g.mol1.

[0382] As an amino polymer iv), polytetrahydrofuran (or polytetramethylene glycol) α, co-diamine, polybutadienes α, co-diamine may also be cited.

[0383] The additional (poly)amine compound(s) iv) may be selected from hyperbranched polymers comprising at least one amino group and dendrimers bearing at least one amino group such as PAMAM polyamidoamine dendrimers with an ethylenediamine core and a terminal amine function.

[0384] Preferably, the additional (poly)amine compound(s) iv) are selected from non-polymer (poly)amine diaminic compounds, non-polymer (poly)amine triamine compounds, diaminic polymers, triamine polymers, polyamine polymers having more than 3 amine functions and mixtures thereof; more particularly from polymeric or non-polymeric compounds (poly)amines, diaminated or triamined, or containing more than 3 primary amine functions.

[0385] More preferably, the additional (poly)amine compound(s) iv) are selected from spermidine, C36 alkylenediamines, in particular priamine such as Priamine™ 1075-LQ-(GD) marketed by CRODA, triamine polyethers, in particular polyethylene glycol and / or polypropylene glycol α,co-triamine (with terminal amine function), diaminopropanols, polyamino acids, in particular polylysine, and mixtures thereof.

[0386] Even better, the additional (poly)amine compound(s) iv) are chosen from spermidine, C36 alkylenediamines in particular priamine, diaminopropanols, triamine polyethers, polylysines and mixtures thereof; even better from 1,3-diaminopropan-2-ol, spermidine, C36 alkylenediamines in particular priamine, polyethylene glycol and / or polypropylene glycol α,co-triamine with terminal amine function such as the Jeffamines T marketed by the Huntsman company and in particular Jeffamine T403, polylysines and mixtures thereof.

[0387] According to a particularly preferred embodiment, the additional (poly)amine compound(s) iv) are selected from spermidine, C36 alkylenediamines in particular priamine, and mixtures thereof.

[0388] Preferably, the total content of additional (poly)amine compound(s) iv) present in a composition is in the range of 0.1% to 40% by weight, more preferably 0.5% to 30% by weight, more preferably 1% to 25% relative to the total weight of the composition comprising it / them.

[0389] Preferably, the total content of (poly)amine compound(s) selected from among diaminated (poly)amine compounds, triamined (poly)amine compounds, and mixtures thereof, present in a composition, is within the range of 0.1% to 40% by weight, more preferably 0.5% to 30% by weight, more preferably 1% to 25% by weight, relative to the total weight of the composition comprising them.

[0390] Preferably, the total content of (poly)amine compound(s) selected from diaminopropanols, triamine polyethers, and mixtures thereof, present in a composition, is in the range of 0.1% to 40% by weight, more preferably 0.5% to 30% by weight, more preferably 1% to 25% by weight, relative to the total weight of the composition comprising them.

[0391] Preferably, when the additional (poly)amine compound(s) iv) and the compounds ii) of formula (I) are present in the same composition, the weight ratio of the total content of compound(s) ii) of formula (I) to the total content of additional (poly)amine compound(s) iv) is in the range of 0.1 to 10; more preferably from 0.5 to 5; better from 0.8 to 2. Organic solvent

[0392] According to the process of the invention, the composition or compositions applied to the keratin fibers may optionally include further one or more organic solvents.

[0393] Examples of organic solvents include: a) C2-C6 alkanols, such as ethanol and isopropanol; b) water-miscible polyols at room temperature (25 °C), in particular polyols having from 2 to 10 carbon atoms, preferably having from 2 to 6 carbon atoms, such as glycerin, propylene glycol, 1,3-propanediol, butylene glycol, pentylene glycol, hexylene glycol, dipropylene glycol, diethylene glycol, diglycerin; c) polyol ethers such as 2-butoxyethanol, propylene glycol monomethyl ether, diethylene glycol monoethyl ether and monomethyl ether, d) aromatic alcohols such as benzyl alcohol or phenoxyethanol, e) esters of C2-C6 acids and C2-C6 alcohols, such as ethyl lactic acid ester (ethyl lactate), f) C6-C16 alkanes, and mixtures thereof

[0394] According to the invention, organic solvents do not carry amine or thiol functions and are in particular different from amino-alkanols such as diaminopropanols.

[0395] Preferably, the organic solvent(s) are chosen from C2-C6 alkanols, such as ethanol and isopropanol, C6-Ci6 alkanes such as isododecane, C2-C6 acid and C2-C6 alcohol esters such as ethyl ester of lactic acid (ethyl lactate), and mixtures thereof.

[0396] Advantageously, the composition or compositions applied are aqueous, hydroalcoholic (advantageously an ethanol / water mixture in particular in a volume ratio of between 1 / 99 to 99 / 1, more particularly between 10 / 90 to 90 / 10, even more particularly between 20 / 80 and 80 / 20, preferably 40 / 60 to 60 / 40 such as 50 / 50), or alcoholic.

[0397] Preferably, the total content of organic solvent(s) in a composition applied to keratin fibers is in the range of 1% to 90% by weight, more preferably 10% to 80% by weight, more preferably 15% to 70% by weight, and even better 20% to 60% by weight, relative to the total weight of the composition.

[0398] The composition or compositions applied to the keratin fibers may optionally include additional water.

[0399] Preferably, the total water content in an applied composition is in the range of 10% to 80% by weight, more preferably 15% to 70% by weight, and even better 20% to 60% by weight, relative to the total weight of the composition.

[0400] Preferably, when a composition applied to keratin fibers includes water, the pH of this composition is between 3 and 12, more preferably between 3.5 and 9, more preferably still between 4 and 7.

[0401] The pH of said composition can be adjusted to the desired value by means of alkalizing agents or acidifying agents commonly used.

[0402] Examples of acidifying agents include mineral or organic acids such as hydrochloric acid, orthophosphoric acid, carboxylic acids such as acetic acid, tartaric acid, citric acid, lactic acid, and sulfonic acids.

[0403] Among the alkalizing agents, ammonia, mineral or organic hydroxides can be cited.

[0404] The composition(s) applied to the keratin fibers may also contain additives commonly used in cosmetics, such as antifoaming agents, thickening agents, moisturizing agents, clays, mineral fillers, UV filters, perfumes, anionic, cationic, nonionic, or amphoteric surfactants, vitamins, preservatives, silicones, waxes, and mixtures thereof. These additives may be present in the composition according to the invention in an amount ranging from 0 to 20% by weight relative to the total weight of the composition.

[0405] A person skilled in the art shall take care to choose any such additives and their quantities so that they do not impair the properties of the compositions of the present invention.

[0406] The use of this or these compositions applied to keratin fibers can be done on wet or dry hair, in rinsed or unrinsed mode.

[0407] The composition(s) applied to the keratin fibers according to the process of the invention may optionally be formulated as a suspension, dispersion, gel, emulsion, in particular an oil-in-water (O / W) or water-in-oil (W / O) emulsion, or multiple (W / O / W or polyol / O / W or O / O / O), in the form of a cream, foam, stick, vesicle dispersion, in particular of ionic or non-ionic lipids, bi-phase or multi-phase lotion. Process

[0408] The process according to the invention comprises applying the following ingredients to said keratin fibers, which are included in one or more separate compositions: (i) at least one chitosan compound as described above; and

[0409] ii) at least one compound of formula (I) as described above;

[0410] iii) at least one colouring agent selected from pigments, direct dyes, and mixtures thereof.

[0411] According to one embodiment of the invention, ingredients i), ii) and iii) are applied simultaneously to the keratin fibers.

[0412] According to one embodiment of the invention, ingredients i), ii), iii) and optionally iv) are applied simultaneously to the keratin fibers.

[0413] Preferably, ingredients i), ii), iii) and optionally iv) are applied to the keratin fibers by means of at least two separate compositions.

[0414] The process may comprise at least 2 steps in which ingredients i), ii) and iii), are applied in separate, successive steps to the keratin fibers.

[0415] Ingredient(s) i) may be applied in a first step to the keratin fibers, then ingredient(s) ii) may be applied in a second step to the keratin fibers, it being understood that ingredient(s) iii) may be applied together with i) and / or ii), preferably with ii).

[0416] According to one embodiment, ingredient(s) i) may be applied in a first step to the keratin fibers, then ingredient(s) ii) may be applied in a second step to the keratin fibers, it being understood that ingredient(s) iii) and optionally iv) may be applied together with i) and / or ii), preferably with ii).

[0417] Ingredient(s) i) may be applied in a first step to the keratin fibers, then ingredient(s) iii) may be applied in a second step to the keratin fibers, it being understood that ingredient(s) ii) may be applied together with i) and / or iii), preferably with iii).

[0418] Ingredient(s) ii) may be applied in a first step to the keratin fibers, then ingredient(s) i) may be applied in a second step to the keratin fibers, it being understood that ingredient(s) iii) may be applied together with i) and / or ii), preferably with ii).

[0419] Ingredient(s) iii) may be applied in a first step to the keratin fibers, then ingredient(s) i) may be applied in a second step to the keratin fibers, it being understood that ingredient(s) ii) may be applied together with i) and / or iii).

[0420] Preferably, ingredient(s) i) are applied in a first step to the keratin fibers, then ingredients ii), iii) and possibly iv) are applied together in a second step to said fibers.

[0421] More preferably, ingredient(s) i) are applied in a first step to the keratin fibers, then ingredients ii) and iii) and iv) are applied together in a second step to said fibers.

[0422] More preferably, the method according to the invention comprises:

[0423] a) an application step on the keratin fibers of at least one pretreatment composition comprising ingredient(s) i), then

[0424] b) an application step on the keratin fibers of at least one coloring composition, distinct from the composition applied in step a), comprising ingredients ii), iii) and optionally iv).

[0425] Preferably, step a) does not implement ingredient ii).

[0426] Preferably, the process for treating keratin fibers involves:

[0427] - a "Cl" composition, comprising i) at least one chitosan compound such as defined previously; preferably the composition Cl does not include ii) a compound of formula (I) as defined previously, nor iii) a coloring agent as defined previously, nor iv) an additional (poly)amine compound;

[0428] - a "C2" composition comprising ii) at least one compound of formula (I) such as defined above; preferably composition C2 does not include i) chitosan compound as defined above, nor iii) coloring agent as defined above, nor iv) additional (poly)amine compound;

[0429] - a "C3" composition comprising iii) at least one coloring agent as defined previously; preferably composition C3 does not comprise i) chitosan compound, nor ii) compound of formula (I) as defined previously,

[0430] - a "C4" composition comprising i) at least one chitosan compound such as defined above and ii) at least one compound of formula (I) as defined above; preferably, composition C4 does not include iii) a coloring agent as defined above nor iv) an additional (poly)amine compound;

[0431] - a composition, referred to as "C5", comprising i) at least one chitosan compound such as defined above and iii) at least one coloring agent as defined above; preferably composition C5 does not include ii) a compound of formula (I) as defined above nor iv) an additional (poly)amine compound;

[0432] - a "C6" composition comprising ii) at least one compound of formula (I) such that defined above and iii) at least one coloring agent as defined above; preferably composition C6 does not include i) chitosan compound as defined above;

[0433] - a composition, referred to as "C7", comprising i) at least one chitosan compound as defined above, ii) at least one compound of formula (I) as defined above and iii) at least one coloring agent as defined above;

[0434] - a composition called "C8", comprising i) at least one chitosan compound such as defined above, ii) at least one compound of formula (I) as defined above and iii) at least one coloring agent as defined above and iv) at least one additional (poly)amine compound;

[0435] - a composition referred to as "C9", comprising ii) at least one compound of formula (I) as defined above and (iii) at least one coloring agent as defined previously and iv) at least one additional (poly)amine compound, composition C9 not comprising i) chitosan compound as defined previously,

[0436] - a so-called "CIO" composition, comprising (iv) at least one (poly)amine compound additional as defined above and optionally iii) at least one coloring agent as defined above, the CIO composition not comprising i) a chitosan compound as defined above or ii) a compound of formula (I),

[0437] it being understood that:

[0438] - the process implements together or separately i) at least one compound chitosan, ii) at least one compound of formula (I) as defined above, iii) at least one coloring agent as defined above, and optionally iv) an additional (poly)amine compound; and

[0439] - the compositions Cl, C2, C3, C4, C5, C6, C7, C8 and C9 can be anhydrous or aqueous such as hydroalcoholic.

[0440] Composition C9 can be obtained by mixing before application several distinct compositions in particular by mixing compositions C2 with C3 and with CIO or by mixing compositions C6 and CIO, preferably by mixing compositions C6 and CIO.

[0441] According to the invention, three modes of implementation are distinguished, called "1-step application mode", "2-step application mode" and "3-step application mode".

[0442] Preferably, when the process is carried out in one step, the C7 or C8 composition as defined above is applied to the keratin fibers.

[0443] The term "one-step application method" means the direct application to the target keratin fibers of a single composition according to the invention, namely composition C7 or composition C8.

[0444] Preferably, the method according to the invention is carried out in two steps.

[0445] The term "2-step application method" means the successive application, on the keratin fibers, of two distinct compositions, in particular Cl and C6, or Cl and C9, more preferably Cl then C6, or Cl then C9, even more preferably Cl then C9.

[0446] The process of the invention can also be carried out in 3 steps.

[0447] The term "3-gesture application mode" refers to the sequential application of 3 distinct compositions. According to this method of application, for example, the following successive applications are made to the keratin fibers: a) a Cl composition, [3] a C6 composition, y) a CIO composition, preferably Cl then C6 then CIO.

[0448] According to a preferred embodiment of the invention, the process comprises applying a Cl composition during a pretreatment step, then at least a composition containing together or in pairs or separately the ingredients ii), iii) and possibly iv) during a coloring step.

[0449] According to a particularly preferred embodiment of the invention, the process comprises the application of a composition Cl during a pre-treatment step, and then of at least one composition containing together or in pairs or separately ingredients ii, iii) and iv) during a coloring step.

[0450] According to this embodiment, the pretreatment composition Cl is applied to dry or moist keratin fibers. When the composition is applied to dry keratin fibers, said fibers are dried in ambient air, or with a hairdryer, preferably with a hairdryer.

[0451] Advantageously, the pretreatment composition Cl is applied to the keratin fibers in a ratio of 0.05 to 10 g of composition per gram of strand, preferably 0.2 to 1.5 g of composition per gram of strand.

[0452] Preferably, the application of the pre-treatment composition Cl is carried out by any conventional means such as a comb, fingers or by deposition techniques such as an aerosol.

[0453] The pretreatment composition Cl comprises i) at least one chitosan compound.

[0454] Advantageously, the chitosan compound i), when present in the pretreatment composition, is present in a content ranging from 0.001% to 20% by weight, preferably from 0.005% to 10% by weight, more preferably from 0.005% to 5% by weight, better from 0.01% to 1% by weight, even better from 0.01% to 0.3% by weight, relative to the total weight of the pretreatment composition.

[0455] Advantageously, the pH of the pretreatment composition is between 3 and 10.

[0456] Advantageously, the pre-treatment composition can be aqueous or hydroalcoholic (water / alcohol mixture or water / solvent mixture miscible with water).

[0457] Preferably, when the pre-treatment composition includes a chitosan compound of formula (Al), the composition is hydroalcoholic.

[0458] Preferably, when the pretreatment composition includes a chitosan compound of formula (A2), the composition is aqueous.

[0459] After application of the pretreatment composition, the keratin fibers can be dried. Preferably, the keratin fibers are dried using a drying device such as a helmet, a hairdryer, or a climazon. When the drying step is carried out with a helmet or a hairdryer, the drying temperature is above 40°C.

[0460] After the drying step, a shaping step of the keratin fibers can be carried out with a keratin fiber shaping device such as a hair straightener, a crimping or curling iron, or a steam iron, preferably an iron a flat iron or steam iron. Preferably, the shaping step is carried out at a temperature above 100°C. The iron can be applied to the keratin fibers in successive touches, each a few seconds apart, or by progressive movement or gliding along the keratin fibers. Preferably, the iron is applied in a continuous movement from the root to the tip of the keratin fibers, in one or more passes.

[0461] After the pre-treatment step, a rinsing step of the keratin fibers can be carried out.

[0462] The term "rinsing step" refers to the application of water to the keratin fibers.

[0463] Preferably, no rinsing step is implemented after the pretreatment step.

[0464] Preferably, at least one staining composition is applied after the pre-treatment step.

[0465] These coloring compositions are applied to dry or moist keratin fibers. When the composition is applied to dry keratin fibers, said fibers are dried in ambient air, or with a hairdryer, preferably a hairdryer.

[0466] Advantageously, during the staining step, a composition A comprising ii) at least one compound of formula (I) as defined above and optionally iii) at least one staining agent as defined above is applied to the keratin fibers, and a composition B comprising an additional (poly)amine compound different from the chitosan compound i) and optionally iii) at least one staining agent, it being understood that at least one of the compositions A and / or B contains iii) at least one staining agent, preferably composition A contains iii) at least one staining agent.

[0467] Preferably, composition A and composition B are mixed extemporaneously to form composition C, and composition C is applied to the keratin fibers during the coloring step.

[0468] Preferably, the application of the colouring composition is carried out by any conventional means such as a comb, fingers or by deposition techniques such as an aerosol.

[0469] Advantageously, the colouring composition can be aqueous or hydroalcoholic (water / alcohol mixture or water / solvent mixture miscible with water).

[0470] After applying the coloring composition, the keratin fibers can be dried. Preferably, the keratin fibers are dried using a drying device such as a hood dryer, a hair dryer, or a climazon. When the drying step is carried out with a hood dryer or a hair dryer, the drying temperature is above 40°C.

[0471] After the drying step, a shaping step of the keratin fibers can be carried out using a keratin fiber shaping device such as a flat iron, a crimping or curling iron, or a steam iron, preferably a flat iron or a steam iron. Preferably, the shaping step is carried out at a temperature above 100°C. The iron can be applied to the keratin fibers in successive touches separated by a few seconds, or by progressive movement or gliding along the hair. Preferably, the iron is applied in a continuous movement from the root to the tip of the hair, in one or more passes.

[0472] After the staining step, a rinsing step of the keratin fibers can be carried out.

[0473] The term "rinsing step" refers to the application of water to the keratin fibers.

[0474] Preferably, no rinsing step is implemented after the coloring step.

[0475] Preferably, the method according to the invention is implemented by a "2-step application method".

[0476] More preferably, the process for coloring keratin fibers, according to the invention, comprises at least the following steps:

[0477] a) an application step on keratin fibers of a Cl composition as described above,

[0478] b) a step of drying the keratin fibers using a drying device,

[0479] c) a step of applying a C6 composition or a C9 composition as described above to the keratin fibers, preferably a C9 composition, and

[0480] d) a step of drying the keratin fibers using a drying device.

[0481] Even more preferably, the process for coloring keratin fibers according to the invention comprises at least the following steps:

[0482] a) an application step on the keratin fibers of a pretreatment composition comprising i) at least one chitosan compound as defined above,

[0483] b) a drying step of the keratin fibers using a drying device,

[0484] c) an application step on the keratin fibers of a coloring composition comprising ii) at least one compound of formula (I) as defined above, iii) at least one coloring agent as defined above and optionally at least one additional (poly)amine compound iv) as defined above, and

[0485] d) a step of drying the keratin fibers, using a drying device.

[0486] Better still, the process for coloring keratin fibers, according to the invention, comprises at least the following steps:

[0487] a) a step of applying a pretreatment composition to the keratin fibers comprising i) at least one chitosan compound as defined above,

[0488] b) a step of drying the keratin fibers using a drying device,

[0489] c) the extemporaneous mixing of a composition A comprising ii) at least one compound of formula (I) as defined above and optionally iii) at least one coloring agent as defined above and of a composition B comprising at least one additional (poly)amine compound iv) and optionally iii) at least one coloring agent as defined above, it being understood that at least one of compositions A and / or B contains at least one coloring agent, preferably composition A contains at least one coloring agent, to form a composition C,

[0490] d) an application step on the keratin fibers of composition C as described above, and

[0491] e) a step of drying the keratin fibers, using a drying device.

[0492] According to a particular embodiment of the invention, the process may include a first pre-treatment step comprising the application to the keratin fibers of at least one chitosan compound i) as defined above, and then a second coloring step comprising the application to the keratin fibers i) of at least one chitosan compound as defined above, ii) of at least one compound of formula (I) as defined above, iii) of at least one coloring agent as defined above and optionally iv) at least one additional (poly)amine compound different from the chitosan compound i). Composition

[0493] The invention also relates to a composition, preferably cosmetic, comprising: - at least one chitosan compound i) as defined above, - at least one beneficial agent chosen from a) coloring agents as defined above, b) compounds of formula (I) as defined above, c) and their mixtures.

[0494] Preferably, the composition further comprises at least one (poly)amine compound (iv), different from chitosan compounds as defined above, compounds of formula (I) as defined above, and coloring agents as defined above. Multi-compartment device (kit)

[0495] Another object of the invention is a device with several distinct compartments comprising: - a first compartment containing i) at least one chitosan compound as defined above and possibly iii) at least one coloring agent as defined above and / or possibly iv) at least one additional (poly)amine compound as defined above, and

[0496]

[0497]

[0498]

[0499]

[0500] - a second compartment, separate from the first, containing ii) at least one compound of formula (I) as defined above and optionally iii) at least one coloring agent as defined above - and possibly a third compartment containing iv) at least one additional (poly)amine compound as defined above and possibly iii) at least one coloring agent, provided that at least one of the compartments contains iii) at least one coloring agent as defined above. The following examples serve to illustrate the invention without being intended to be limiting. Examples Preparation of compounds The compounds of formula (I) as described below are used in the compositions exemplified below: Formula compound (I) #1: Castor oil with acetoacetate function (HE The synthesis is represented by the following preparation diagram: Step a): Step b): Step c):

[0501] In step a), 451 g of castor oil (commercially available from Interchimie) and 171 g of glutaric anhydride are introduced into a 750 mL SVL® reactor equipped with a condenser, mechanical stirring, and an argon inlet. The reaction mixture is heated in an oil bath at 150°C (see oil bath instructions) for 5 hours. The reaction is monitored by NMR.

[0502] In step b), 600 g of castor oil modified with glutaric acid and 134 g of glycerol are introduced into a 500 mL SVL® reactor equipped with a distillation apparatus, mechanical stirring, and an argon supply. The reaction mixture is heated using a heating mantle for 4 hours at 190°C and then for 11 hours at 230°C. The reaction is monitored by acid value.

[0503] In step c), 600 g of glycerol-modified castor oil and 418 g of tert-butyl acetoacetate are introduced into a 1000 mL SVL® reactor equipped with a distillation apparatus, mechanical stirring, and an argon supply. The reaction mixture is heated in an oil bath at 150°C (as specified on the oil bath) for 5 hours. The reaction mixture is then placed in a rotary evaporator at 150°C under continuous vacuum to remove any unreacted tert-butyl acetoacetate.

[0504] Compound of formula (I) #2: Sucrose palmitate with acetoacetate function

[0505] In a 500 mL three-necked flask equipped with a mechanical stirrer and a distillation column, 100 g of sucrose palmitate ester (Surfhope® SE Cosme C-1616, marketed by Mitsubishi-Kagaku Foods Corporation) and 110 g of tert-butyl acetoacetate are introduced. The mixture is heated in an oil bath at a temperature between 140°C and 150°C (as indicated on the oil bath) for 2 hours. The reaction mixture is then concentrated using a rotary evaporator at 140°C under continuous vacuum until constant weight is reached.

[0506] The additional (poly)amine compounds iv) as described below are used in the compositions exemplified below:

[0507] [Tables 1] Polyamine Compound 1 Polyamine Compound 2 Priamine 1075-LQ-(GD) CAS number: 68955-56-6 Supplier: CRODA Spermidine CAS number: 124-20-9 Supplier: Sigma Aldrich NH₂ x = 6^7 or 8 H H₂N N ^NH₂

[0508] Example 1: Process for the synthesis of Palmitoyl Glycol Chitosan

[0509] In a 20 L double-jacketed container, equipped with a thermometer and a stirrer, 68.24 g of 2,5-dioxopyrrolidin-l-yl palmitate and 12 L of an ethanol / methanol mixture at a volume ratio of 95 / 5 were introduced under stirring at a temperature of 30°C for 1 hour.

[0510] 6 kg of water are then introduced into the reaction medium followed by 30 g of sodium bicarbonate, and the said medium was stirred until the sodium bicarbonate was dissolved.

[0511] After dissolving the sodium bicarbonate, 40 g of chitosan glycol were introduced and the mixture was stirred at 35°C for 1 hour. The solution was then cooled to 25°C and 2 L of an ethanol / methanol mixture at a volume ratio of 95 / 5 were added. The solution was then stirred for 6 days.

[0512] After 6 days, the reaction medium was distilled under vacuum and the suspension was transferred into dialysis tubes and then dialyzed in water for 4 days, with the water being renewed every 4 hours (except at night).

[0513] The dialysis tubes were then opened and the recovered white sludge was dried for several days in a ventilated tube set at 40°C to give 53.3 g of a light brown solid. Example 2

[0514] Compositions 1 to 6 as described in Tables 2 and 3 were prepared: quantities are expressed as % mass of raw material as is, unless otherwise stated.

[0515] [Tables2] Ingredients Formulas 1 2 3 4 5 6 Palmitoyl Glycol Chitosan (from example 1) 0.1 - - - - - Sodium Chitosan Rice Branamide Hydroxypropylsulfonate - 0.25 - - - - Castor oil (acetoacetate function) - - 10.0 - - - Sucrose palmitate (acetoacetate function) - - - - 10.2 - Priamine - - - 8.4 - - Spermidine - - - - - 4.2 Red iron oxide - - 5.1 2.0 - Ethyl lactate - - q.s. 100 q.s. 100 - - Isododecane / Ethanol (1 / 1 w / w) - - - - q.s. 100 q.s. 100 Water / Ethanol (1 / 1 w / w) q.s. 100 - - - - - Water - q.s. 100 - - - -

[0516] A Compl composition was prepared by mixing in a bowl and with a brush, formula 3 and formula 4, according to the weight ratio formula 3 / formula 4 of 1:1.

[0517] Formula 1 was also used and is referred to as Tl in the rest of the example.

[0518] The compositions Tl and Cl are summarized in the table below:

[0519] [Tables3] Compositions Mixture of formulas (Rap weight range) Tl Formula 1 Compl Formulas 3 + 4(1:1)

[0520] Protocol:

[0521] Two processes were implemented on strands of 90% white, cleaned and natural hair, of 1 g.

[0522] According to the PI process, composition Tl was first applied to the hair strands at a rate of 1 g of composition per gram of strand, using a brush. The application of composition Tl was followed by a processing time of 30 minutes at a temperature of 33°C. The excess formula on the strands was then removed by pressing the hair between the thumb and forefinger and repeating the operation a second time. The hair strands were then left to dry in an oven at 60°C for 10 minutes.

[0523] Composition Compl was then applied to the strands previously treated with composition Tl at a rate of 0.4 g of composition per gram of strand, using a pipette, distributing the composition on both sides of the strands. The strands were then blow-dried for 3 minutes using a comb. The strands were then shampooed twice according to the shampooing protocol 1 described below.

[0524] According to process P2, the Compl composition was applied to the hair strands at a rate of 1 g of composition per gram of strand, using a pipette, distributing the composition on both sides of the strands. The strands were then blow-dried for 3 minutes, using a comb. The strands then underwent two repeated shampooings according to the shampooing protocol 1 described below.

[0525] The PI process is a process according to the invention.

[0526] The P2 process is a comparative process. Shampoo Protocol 1

[0527] The colored hair strands are combed, moistened under water at 35°C before being passed between the fingers 5 times for 5 seconds. The hair strands are then squeezed between two fingers.

[0528] A standard shampoo (Garnier Ultra Doux) is applied evenly to the colored strands at a rate of 0.4g of standard shampoo per gram of strands, gently massaging the strands of hair along their length (6 passes) for 15 seconds, from root to tip.

[0529] The strands of hair are then placed in a watch glass and left to rest for 1 minute.

[0530] Next, the hair strands are rinsed with water by passing the strand between the fingers (15 passes). The hair strands are then squeezed dry between two fingers before the next shampoo.

[0531] After the shampooing cycles, the strands are left to dry in the oven at 60°C for 10 minutes / g of hair.

[0532] The processes applied are summarized in the table below:

[0533] [Tables4] Processes Application of PI compositions (invention) Tl + Compl P2 (comparative) Compl

[0534] The hair strands treated by the PI and P2 processes were then subjected to a color resistance test to rub in order to evaluate the tenacity (the persistence) of the color obtained by rubbing.

[0535] Protocol for the colorfastness test on rubbing

[0536] This test is an adaptation of a test described in the standardized test NF EN ISO 105-X12:2016 which specifies a method for determining the resistance to rubbing of dyes on textiles of all kinds.

[0537] A device called a Crockmeter (supplier Roaches International Limited, UK) is used. Originally designed to simulate the action of a human finger and forearm, the Crockmeter uses a standard pressure and friction motion to provide reliable and reproducible test results.

[0538] The samples are placed on the base of the Crockmeter and held in place by the sample holder. To prevent the specimen from moving during the test, a sandpaper pad is provided to be placed under the specimen.

[0539] A hand crank moves a reciprocating arm over a distance of approximately 100 mm. The frictional action is provided by a 16 mm diameter acrylic "finger" that moves back and forth in a straight line with each complete revolution of the crank. The reciprocating load arm is weighted to provide a constant load of 9 N on the sample at all times, and a mechanical counter keeps track of the completed cycles.

[0540] A square of cotton fabric ('Crocking Cloths (Gimped) Code: 50WW-0015 / CC / SD from Roaches International Limited) is wrapped around the "finger" of the acrylic jar and held in place by a spring clip.

[0541] Two tests are planned, one by rubbing the hair with a dry cloth and the other by rubbing it with a damp cloth. Five cycles are performed, then the cotton cloth is removed from the apparatus and the amount of color transferred from the dyed hair to the cotton by rubbing is evaluated using a columnar scale known as "grey scales". The use of the scale is described in ISO 105-A02 / IUF131 - GREY SCALE FOR ASSESSING CHANGE IN COLOUR. The grey scale has 9 possible values, in half-point increments, from 1 to 5. value between 1 = significant variation (worst score - much color transfer) and 5 = no variation (best score - no color transfer).

[0542] The results are summarized in the table below:

[0543] [Tables5] Process Value (grayscale) Dry Test Wet Test Observations PI (invention) 5 4.5 No transfer in dry test Little transfer in wet test P2 (comparative) 5 3.5 No transfer in dry test Transfer in wet test

[0544] The color of hair strands treated with PI exhibits improved resistance to friction, compared to the color of hair strands treated with P2. Example 3

[0545] A Comp2 composition was prepared by mixing in a bowl and with a brush, formula 5 and formula 6, according to the weight ratio formula 5 / formula 6 of 1:1.

[0546] Formula 2 was also used and is referred to as T2 in the rest of the example.

[0547] Compositions T2 and Comp2 are summarized in the table below:

[0548] [Tableauxô] Compositions Mixture of formulas (Rap weight range) T2 Formula 2 Comp2 Formulas 5+6(1:1)

[0549] Protocol:

[0550] Two processes were implemented on strands of 90% white, cleaned and natural hair, of 1 g.

[0551] According to process P3, composition T2 was first applied to the hair strands at a rate of 1 g of composition per gram of strand, using a brush. The application of composition T2 was followed by a processing time of 15 minutes at a temperature of 33°C. The excess formula on the strands was then removed by pressing the hair between the thumb and forefinger and repeating the operation a second time. The hair strands were then left to dry in an oven at 60°C for 10 minutes.

[0552] Composition Comp2 was then applied to the strands previously treated with composition T1 at a rate of 0.6 g of composition per gram of strand, at Using a pipette, the mixture was distributed on both sides of the strands. The strands were then blow-dried for 3 minutes, using a comb.

[0553] According to process P4, composition Comp2 was applied to the hair strands at a rate of 0.6 g of composition per gram of strand, using a pipette, distributing the composition on both sides of the strands. The strands were then dried with a hairdryer for 3 minutes, using a comb.

[0554] The P3 process is a process according to the invention.

[0555] The P4 process is a comparative process.

[0556] The processes implemented in Example 3 are summarized in the table below:

[0557] [Tables?] Processes Application of compositions P3 (invention) T2 + Comp2 P4 (comparative) Comp2

[0558] The hair strands treated by processes P3 and P4 were then subjected to 5 shampooing cycles according to the shampooing protocol 1 described above, in order to evaluate the tenacity (residual effect) of the obtained color to shampooing. Results

[0559] The persistence of the color of the highlights was evaluated in the CIE L*a*b* system, using a Minolta CM3610d spectrophotometer (illuminant D65, angle 10°, specular component included).

[0560] In this L*a*b* system, L* represents the intensity of the color, a* indicates the green / red color axis and b* the blue / yellow color axis.

[0561] Color permanence is assessed by the color difference AE between the colored strands before 5 shampooing cycles, and then after 5 shampooing cycles. The lower the AE value, the more the color persists through shampooing. The value of AE is calculated according to the following equation: ■ae =

[0562] In this equation, L*, a* and b* represent the values ​​measured after hair coloring and after undergoing the 5 shampoo cycles, and Lo*, a0* and b0* represent the values ​​measured after hair coloring but before the 5 shampoo cycles.

[0563] The results are summarized in the table below:

[0564] [Tables8] Processes After coloring After 5 shampoos AE Lo* a0* bo* L* a* b* P3 (invention) 37.9 26.5 23.8 40.9 21.9 23.0 5.6 P4 (comparative) 36.5 27.6 23.6 43.8 20.0 23.5 10.5

[0565] Hair strands treated with P3 show improved shampoo retention compared to hair strands treated with P4. Example 4

[0566] Compositions 7 to 8 as described in Table 9 were prepared: quantities are expressed as % mass of raw material as is, unless otherwise stated.

[0567] [Tables9] Ingredients Formulas 7 8 Palmitoyl Glycol Chitosan of example 1 6.0 Castor oil with acetoacetate function 10.0 Red iron oxide 12.0 Ethyl lactate q.s. 100 q.s. 100

[0568] A Comp3 composition was prepared by mixing in a bowl and with a brush, formula 7 and formula 8, according to the weight ratio formula 7 / formula 8 of 1:1.

[0569] The composition Comp3 is summarized in the table below:

[0570] [TableauxlO] Composition Mixture of formulas (Rap weight range) Comp3 Formulas 7 + 8 (1:1)

[0571] Protocol:

[0572] The P5 process was carried out on strands of 90% white, cleaned and natural hair, of 1 g.

[0573] According to process P5, composition Comp3 was applied to the strands at a rate of 1 g of composition per gram of strand, using a pipette, distributing the composition on both sides of the strands. The strands were then dried with a hairdryer for 3 minutes, using a comb. Results

[0574] The rise in the colour of the highlights was evaluated in the CIE L*a*b* system, using a Minolta CM3610d spectrophotometer (illuminant D65, angle 10°, specular component included).

[0575] In this L*a*b* system, L* represents the intensity of the color, a* indicates the green / red color axis and b* the blue / yellow color axis.

[0576] The persistence of the color is evaluated by the color difference AE between the uncolored strands and the colored strands

[0577] The value of AE is calculated according to the following equation: AE =

[0578] In this equation, L*, a* and b* represent the values ​​measured after hair coloring, and Lo*, a0* and b0* represent the values ​​measured before hair coloring.

[0579] The results are summarized in the table below:

[0580] [Tables 11 Process Before coloring After coloring AE Lo* a0* bo* L* a* b* P5 (inventio n) 55.9 0.1 11.5 33.0 22.7 17.4 32.6

[0581] The strands of hair treated by the P5 process according to the invention exhibit a good colour rise.

Claims

Demands

1. A process for coloring keratin fibers comprising applying to said keratin fibers the following ingredients, which are included in one or more separate compositions: i) at least one chitosan compound comprising at least 2 repeating units, different from each other, of the following general formula (A): in which: - RI independently represents a hydrogen atom or a group -(CH2CH(R')Y)qX in which: - X denotes a hydrogen atom or a radical -SO3, M+ or a radical N+(R'i)3, An - q denotes an integer ranging from 1 to 20, - Y designates an oxygen atom or a divalent methylene radical -CH2-; - R' independently represents a hydrogen atom, a methyl group, or a hydroxyl group. - R'i independently represents an alkyl group in Ci-C4, - An represents a mineral or organic anion, preferably with a single charge, such as a halide, sulfate, sulfonate, carboxylate; - M+ represents a mineral or organic cation, preferably with a single charge, such as an alkali metal cation like sodium or potassium; - R2 represents a hydrogen atom, a -C(O)R”'- group, or a group chosen from -CH2CH(R')-CH2-SO3, M+ or -CH2CH(R')-CH2-N+(R'i)3 , An in which R' is as defined above and -R'” represents a CrC3O hydrocarbon radical, saturated or unsaturated, linear or branched, possibly substituted by at least one hydroxyl group, it being understood that: - at least one of the RI radicals is different from a hydrogen atom; and - at least one of the RI radicals designates a hydrogen atom; and - at least one of the R2 radicals designates a hydrogen atom; and - at least one of the R2 radicals is different from a hydrogen atom and different from -CO-CH3-; ii) at least one compound of the following formula (I): () (H)pZ-(Y-AK2)m [(0)t-(AKD q -(0-CO^ in which: - Z represents a multivalent hydrocarbon radical in C2 to C40, in particular in C3 to C36, linear or branched, saturated or unsaturated, conjugated or not, acyclic or cyclic, aromatic or not, Z possibly being interrupted by one or more heteroatoms or groups chosen from -O-, -N(Ra)-, -S-, -C(O)-, (hetero)cycle(s) and / or their combinations; - AK1 represents a divalent hydrocarbon chain, linear or branched, saturated or unsaturated, in C1-C12, preferably in Ci-C6, more preferably saturated in Ci-C6; - AK2 represents a monovalent hydrocarbon chain, linear or branched, saturated or unsaturated, in the C1-C40 range, optionally substituted by one or more radicals, identical or different, chosen from -OR, -X-AK3-(OC(O)-C(Ra)(Rb)-C(O)-R4)v; and / or said chain being optionally interrupted by one or more heteroatoms or groups chosen from -O-, -S-, -C(O)-, (hetero)cycle(s), and their

2. combinations, in particular -O-(CO)-, -(CO)-O-, -(hetero)cycle-O-(hetero)cycle-; - AK3 represents a divalent hydrocarbon chain, linear or branched, saturated or unsaturated, in C1-C12, preferably in Ci-C6, more preferentially saturated in Ci-C6, even more preferentially in C1-C4; - R represents a hydrogen atom, an alkyl radical, linear or branched, saturated or unsaturated, in Ci-C6, preferably in C1-C4, in particular methyl, or a -C(0)-C(Ra)(Rb)-C(0)-R4 radical; - X represents -O-, -S-, -OC(O)- or -C(O)-O-; - Y represents -OC(O)- or -C(O)-O-; - R4 represents a monovalent hydrocarbon radical in C1 to C6, linear or branched, saturated or unsaturated, preferably a (Ci-C4)alkyl group, in particular methyl or tert-butyl, more preferably methyl; - Ra and Rb, whether identical or different, represent a hydrogen atom or a (C1-C4)alkyl group, preferably a hydrogen atom; - p denotes an integer equal to 0 or 1; - m denotes an integer equal to 0, 1, 2, 3 or 4; it being understood that when m is greater than 1, then the radicals -Y-AK2 are identical or different; - n denotes an integer equal to 0, 1, 2, 3 or 4; it being understood that when n is greater than 1, then the radicals -(O)t-(AKi)q-(OC(O)-C(Ra)(Rb)-C(O)-R4)u are identical or different; -1 denotes an integer equal to 0 or 1; - q denotes an integer equal to 0 or 1; - u denotes an integer equal to 1, 2 or 3; - v denotes an integer equal to 1, 2 or 3; it being understood that if q is equal to 0 then t is equal to 0, that (m + n) is greater than or equal to 1, and that the compounds of formula (I) contain at least two -C(O)-C(Ra)(Rb)-C(O)-R4 groups; and iii) at least one coloring agent selected from pigments, direct dyes, and mixtures thereof. A method according to the preceding claim, characterized in that the chitosan compound is selected from: a. Chitosan compounds with the following formula (Al): in which: - RI independently represents a hydrogen atom or a group -(CH2CH(R')O)qH in which: - q denotes an integer ranging from 1 to 20, - R' independently represents a hydrogen atom, a methyl group or a hydroxyl group, preferably a hydrogen atom; -R'” represents a C5-C29 hydrocarbon radical, saturated or unsaturated, linear or branched, possibly substituted by at least one hydroxyl group, it being understood that at least one of the RI radicals is different from hydrogen; - n is a number representing 50% to 99.9% of the sum n + m + P, - m is a number representing 0% to 25% of the sum n + m + p, - p is a number representing 0.1% to 30% of the sum n + m + p, and - the sum n + m + p being equal to 100%; b. chitosan compounds with the following formula (A2): in which: - RI independently represents a hydrogen atom or a group -(CH2CH(R')CH2)X in which: - X denotes a radical -SO3, M+ or a radical N+(R'i)3 , An - R' independently represents a hydrogen atom, a methyl group or a hydroxyl group, preferably a hydroxyl radical; - Rf independently represents an alkyl group in C1-C4, preferably methyl; An, M+ are such as defined for formula (A) in claim 1, - R3 represents a hydrogen atom, a -C(O)R”'- group, or a group chosen from -CH2CH(R')-CH2-SO3, M+ or -CH2CH(R')-CH2-N+(R'i)3 , An in which R', An-, M+ are such as defined for formula (A) in claim 1, and -R'” represents a C5-C29 hydrocarbon radical, saturated or unsaturated, linear or branched, possibly substituted by at least one hydroxyl group, - n is a number representing 70% to 99% of the sum n + m + p, - m is a number representing 0% to 25% of the sum n + m + p, - p is a number representing 1% to 30% of the sum n + m + p, and - the sum n + m + p being equal to 100%, c. and their mixtures.

3. A method according to any one of the preceding claims, characterized in that the total content of chitosan compound(s) i) present in a composition is in the range of 0.001% to 20% by weight, preferably 0.005% to 10% by weight, more preferably 0.005% to 5% by weight, better 0.01% to 1% by weight, even better 0.01% to 0.3% by weight, relative to the total weight of the composition containing it / them.

4. A method according to any one of the preceding claims, characterized in that the compound(s) of formula (I) are selected from the following compounds of formula (la): Z-(Y-AK2)3 (la) formula (la) in which: - Z represents -CH2-CH-CH2- ; - AK2 independently designates a linear or branched, saturated or unsaturated, monovalent hydrocarbon chain, in Ci2-C24, optionally substituted by one or more identical or different radicals selected from -OR and -X-AK3-(OC(O)-C(Ra)(Rb)-C(O)-R 4)v; and / or said chain being optionally interrupted by one or more heteroatoms or groups selected from -O-, -S-, -C(O)-, epoxides, and their combinations, in particular -OC(O)- and -C(O)-O- - Y, AK3, v, R, X, R4, Ra and Rb being such as defined for formula (I) in claim 1, preferably Y denotes -OC(O)-; it being understood that said compound contains at least 2 C(O)-C(Ra)(Rb)-C(O)-R4 radicals.

5. A method according to any one of claims 1 to 3, characterized in that the compound(s) of formula (I) are selected from the following compounds of formula (Ib): m(AK2 -Y) - Z - [(O)t-(AKl)q-(OC(O)-C(Ra)(Rb)-C(O)-R4)u]n (Ib) formula (Ib) in which: - n + m is equal to 4, m being non-zero; m and n being such as defined for formula (I) in claim 1; - Z represents a tetravalent hydrocarbon radical in C2 to C24, in particular in C3 to C10, preferably in C3, unsubstituted and uninterrupted, linear or branched, saturated or unsaturated, preferably saturated and acyclic; - AK2 independently represent a linear or branched monovalent hydrocarbon chain, saturated or unsaturated, preferably saturated, in Ci2-C24, preferably in Ci6-C20, preferably in C[8, optionally substituted by one or more identical or different radicals chosen from -OR, -X-AK3-(OC(O)-C(Ra)(Rb)-C(O)-R4)v, preferably substituted by one or more radicals -X-AK3-(OC(O)-C(Ra)(Rb)-C(O)-R4)v; and / or said chain being optionally interrupted by one or more heteroatoms or groups chosen from -O-, -S-, -C(O)-, (hetero)cycle(s), and their combinations, in particular -OC(O)-, -C(O)-O- or -(hetero)cycle-O-(hetero)cycle-, preferably being uninterrupted; - AK3 represents a linear or branched divalent hydrocarbon chain saturated or unsaturated in CrCi2, preferably in Ci-C6, more preferably saturated in Ci-C6, even more preferably in C2-C4, preferably in C3;- v is as defined in claim 1, preferably v is equal to 2; - X is as defined in claim 1, preferably X denotes a sulfur atom; - Y, AK1, t, q, u, R, R4, Ra and Rb being as defined for formula (I) in claim 1; it being understood that said compound contains at least 2 radicals -C(O)-C(Ra)(Rb)-C(O)-R4.;

6. A method according to any one of claims 1 to 3, characterized in that the compound(s) of formula (I) are chosen from the following compounds of formula (the): m(AK2 -Y) - ZH - [(O)t-(AKl)q-(OC(O)-C(Ra)(Rb)-C(O)-R4)u]n (the) formula (the) in which: - Z represents a multivalent hydrocarbon radical in CM to C24, particularly in Ci6 to C20 such as Cp, linear or branched, saturated or unsaturated, preferably saturated and acyclic, Z being further optionally substituted by one or more radicals -[(O)t-(AKl)q-(OC(O)-C(Ra)(Rb)-C(O)-R4)u]n, preferably unsubstituted; - AK2 represents a linear or branched monovalent hydrocarbon chain, saturated or unsaturated, preferably saturated, in C14-C30, preferably in C20-C29, substituted by one or more identical or different radicals chosen from -OR and -X-AK3-(0-C(0)-C(Ra)(Rb)-C(O)-R4)v, preferably substituted by one or more -OR radicals; and / or said chain being optionally interrupted by one or more heteroatoms or groups selected from -O-, -S-, -C(O)-, (hetero)cycle(s), and their combinations, in particular -O-C(O)-, -C(O)-O- or (hetero)cycle-O-(hetero)cycle, preferably interrupted by -OC(O)- or -C(O)-O-; - X is such as defined for formula (I) in claim 1, and preferably X designates a sulfur atom; - Y, AK1, AK3, n, m, v, t, q, u, R, R4, Ra and Rb being such as defined for formula (I) in claim 1; it being understood that said compound contains at least 2 -C(O)-C(Ra)(Rb)-C(O)-R4 radicals.

7. A method according to any one of claims 1 to 3, characterized in that the compound(s) of formula (I) selected from the following compounds of formula (Id): m(AK2-Y)-Z-[(O)t-(AKl)q-(OC(O)-C(Ra)(Rb)-C(O)-R4)u]n (Id) formula (Id) in which: - n + m is equal to 4, preferably m is equal to 3; - Z represents a tetravalent hydrocarbon radical in C2 to C24, in particular in C3 to C10, in particular in C4 or C5, linear or branched, saturated or unsaturated, preferably saturated or acyclic, Z being further substituted by one or more radicals -[(O)t-(AKl)q-(O-C(O)-C(Ra)(Rb)-C(O)-R4)u]n, preferably n is equal to 1;- AK2 independently represents a linear or branched monovalent hydrocarbon chain, saturated or unsaturated, preferably saturated, in Ci4-C30, preferably in Ci6-C24, preferably in Cp, said chain being optionally substituted by one or more identical or different radicals selected from -OR or -X-AK3-(O-C(O)-C(Ra)(Rb)-C(O)-R4)v, preferably substituted by one or more -OR radicals; and / or said chain being optionally interrupted by one or more heteroatoms or groups selected from -O-, -S-, -C(O)-, (hetero)cycle(s), and their combinations, in particular -OC(O)-, -C(O)-O- or (hetero)cycle-O-(hetero)cycle, preferably being uninterrupted; X is as defined for formula (I) in claim 1, preferably X denotes a sulfur atom; Y, AK1, AK3, v, R, R4, Ra and Rb being such as defined for formula (I) in claim 1,; it being understood that these compounds contain at least 2 radicals -C(O)-C(Ra)(Rb)-C(O)-R4.

8. A method according to any one of claims 1 to 3, characterized in that the compound(s) of formula (I) are chosen from the following compounds of formula (the): m(AK2-Y) - Z - [(O)t-(AKl)q-(OC(O)-C(Ra)(Rb)-C(O)-R4)u]n (the) formula (the) in which: - n + m is equal to 2, m being non-zero, preferably m being equal to 2; n is such as defined for formula (I) in claim 1, preferably n is zero; - Z represents a divalent hydrocarbon radical in C2 to C24, in particular in C3 to Ci2, linear or branched, saturated or unsaturated, conjugated or not, preferably not conjugated, acyclic or cyclic, aromatic or not, preferably not aromatic, said radical Z being further interrupted by one or more heteroatoms or groups chosen from -O-, -N(Ra)-, -S-, -C(O)-, (hetero)cycle(s), and their combinations;preferably Z denotes a divalent radical -(CH2)g-(heterocycle)-O-(CH2)h-(heterocycle)-(CH2)j- in which h denotes 0, 1 or 2, preferably 0 or 1, g and j independently denote an integer between 1 and 3, preferably 1; (heterocycle) denotes a heterocyclic divalent radical, preferably a heterocycloalkyl radical, more particularly a heterocycloalkyl divalent radical comprising 5 or 6 links, in particular a tetrahydrofuran divalent radical or a tetrahydropyran divalent radical, said heterocycle being optionally substituted by one or more radicals selected from -OR with R as defined for formula (I) in claim 1, and in particular -OH or -OC(O)-C(Ra)(Rb)-C(O)-R4);- AK2 represents a linear or branched monovalent hydrocarbon chain, saturated or unsaturated, preferably saturated, in Ci4-C30, preferably Ci4-C24, preferably in Cp, said chain being optionally substituted by one or more identical or different radicals chosen from -OR and -X-AK3-(OC(O)-C(Ra)(Rb)-C(O)-R4)v, preferably unsubstituted; and / or said chain being optionally interrupted by one or more heteroatoms or groups chosen from -O-, -S-, -C(O)-, (hetero)cycle(s), and their combinations, in particular -OC(O)-, -C(O)-O- or -(hetero)cycle-; O-(hetero)cycle-, preferably possibly interrupted by -O-C(O)- or -C(O)-O-, and more preferably uninterrupted; - X is such as defined for formula (I) in claim 1, preferably X designates a sulfur atom; - Y, AK1, AK3, v, t, q, u, R, R4, Ra and Rb being such as defined for formula (I) in claim 1; it being understood that said compound contains at least 2 C(O)-C(Ra)(Rb)-C(O)-R4 radicals.

9. A method according to any one of the preceding claims, characterized in that the total content of compound(s) of formula (I) present in a composition is in a range from 0.1% to 60% by weight, preferably from 1% to 40% by weight, and more preferably from 3% to 20% by weight, relative to the total weight of the composition containing it / them.

10. A method according to any one of the preceding claims, characterized in that the coloring agent(s) are chosen from pigments.

11. A process according to any one of the preceding claims, characterized in that the total content of coloring agent(s) in a composition is in a range from 0.001% to 20% by weight, preferably from 0.005% to 15% by weight, relative to the total weight of the composition containing it / them.

12. A method according to any one of the preceding claims, characterized in that at least one additional (poly)amine compound iv), other than chitosan compounds i), compounds ii) and coloring agents iii), is further applied to the keratin fibers.

13. A method according to any one of the preceding claims, characterized in that ingredients i), ii), iii) and optionally iv) are applied to the keratin fibers by means of at least two separate compositions.

14. A method according to any one of the preceding claims, characterized in that it comprises: - an application step on the keratin fibers of at least one pre-treatment composition comprising ingredient(s) i), then - an application step on the keratin fibers of at least one coloring composition comprising ingredients ii) and iii), and optionally iv), separate from the pre-treatment composition.

15. Composition comprising: - at least one chitosan compound i) as defined in claims 1 and 2, - at least one beneficial agent selected from a) coloring agents as defined in claims 1 and 10, b) compounds of formula (I) as defined in claims 1 and 4 to 8, c) and mixtures thereof.

16. Composition according to the preceding claim, characterized in that it further comprises at least one additional (poly)amine compound iv) as defined in claim 12.

17. A device with several distinct compartments comprising: - a first compartment containing i) at least one chitosan compound as defined in claims 1 and 2 and optionally iii) at least one coloring agent as defined in claims 1 and 10 and / or optionally iv) at least one additional (poly)amine compound as defined in claim 12, and - a second compartment distinct from the first, containing ii) at least one compound of formula (I) as defined in claims 1 and 4 to 8 and optionally iii) at least one coloring agent as defined in claims 1 and 10, - and optionally a third compartment containing iv) at least one additional (poly)amine compound as defined in claim 12, and optionally iii) at least one coloring agent as defined in claims 1 and 10,provided that at least one of the compartments contains iii) at least one coloring agent as defined in claims 1 and 10.

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