A process for treating keratin fibers using one or more compounds with acetoacetate functional groups and one or more specific polyamine compounds

Abstract

The present invention relates to a process for treating keratin fibers using one or more compounds with acetoacetate functions, one or more specific polyamine compounds and optionally one or more coloring agents.

Description

Title of the invention: Process for treating keratin fibers using one or more compounds with acetoacetate functional groups and one or more specific polyamine compounds. Technical field of the invention

[0001] The present invention relates to the cosmetic field of keratin fibers, and in particular to the care, shaping and / or coloring of keratin fibers, and preferably hair. It aims to provide a process for treating keratin fibers comprising applying to the keratin fibers at least one compound with acetoacetate functions, at least one specific polyamine compound and optionally at least one coloring agent. Context of the invention

[0002] Cosmetic products for the temporary coloring of keratin fibers classically require the implementation of one or more film-forming polymers in order to obtain a quality deposit of these products on the keratin fibers, and in particular giving satisfaction to the expectations detailed below.

[0003] 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 function 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 of pigments on the keratin fibers that would meet all the aforementioned requirements, namely very good water resistance, especially with hair shampoos, the ability to adjust shine or invisibility, and, in the case of hair application, very satisfactory hold during styling.

[0004] US document 2006 / 0079599 describes a medical polymer-based tissue adhesive in which certain ACAC group polymers are associated with polyamines in the form of a hydrogel.

[0005] 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.

[0006] There is therefore a real need to make available processes for treating keratin fibers which allow for intense, chromatic colours with good colour rise, as well as good resistance to water and to one or more shampoos, in order to guarantee colour retention over time, particularly in terms of intensity and / or chromaticity.

[0007] It is also of interest to develop non-coloring treatment processes that allow for the lasting shaping of keratin fibers, notably with a substantial reduction in hair volume and, in the case of curly hair, improved curl relaxation and / or better definition. The effect obtained must also be resistant to water and one or more shampoos to ensure that the shaping lasts over time. Finally, the formulation of environmentally friendly cosmetic products—that is, products whose design and development take environmental issues into account—is becoming a major concern in order to contribute to meeting global challenges. It is therefore essential to offer more sustainable cosmetic treatment processes that address these environmental issues.

[0008] The applicant has surprisingly discovered that all or part of these objectives can be achieved by the process according to the present invention. Summary of the invention

[0009] According to a first aspect, the present invention relates to a process for treating keratin fibers by applying the following to the keratin fibers: (i) one or more compounds A chosen from compounds of formula (I) and / or (I'), their optical isomers, their geometric isomers, their salts, their solvates such as hydrates, and their mixtures: (I) (H)p - Z - (Y-AK2) m [(OHAK1MO-C(O)<'(^ Formula (I) 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 may possibly be interrupted by one or more groups or heteroatoms chosen from -O-, -N(Ra)-, -S-, -C(O)-, (hetero)cycles, and 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, 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)-, (hetero)cycle(s), and their combinations, in particular -OC(O)-, -C(O)-O- and / or -(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; 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; Formula (!') in which: - R1 represents a versatile hydrocarbon radical in C2 to CM, linear or branched, saturated or unsaturated, conjugated or not, acyclic or cyclic, aromatic or not, R1 being further: a) possibly substituted by one or more hydroxy groups OH, dialkylamino-N(R)2 with R representing a (Ci-C4)alkyl group, carboxy-C(O)-OH, a vinyl group, and / or b) possibly interrupted by one or more heteroatoms or groups selected from O, S, carbonyl -C(O)-, amine -N(R'), or their combinations, in which R' represents a hydrogen atom, a linear or branched alkyl group having from 1 to 4 carbon atoms possibly substituted by at least one hydroxy group (OH) or possibly substituted by -XC(O)-C(Ra)(Rb)-C(O)-R2; - R2 represents a monovalent hydrocarbon radical in C1 to C6, linear or branched, saturated or unsaturated; - Ra, and Rb, identical or different, represent a hydrogen atom or a (CrC4)alkyl group; - X is a heteroatom or group chosen from O, S, N(R') or , -S-CH2-C(O)-O-, -OC(O)-CH2-S-, -OC(O)-N(R')-, -N(R')-C(O)-O-, -N(R')-C(O)-N(R')-, R' being as defined previously; - n denotes an integer ranging from 2 to 10, particularly from 3 to 9; ii) one or more polyamine compounds B selected from compounds of formula (II), their optical isomers, their geometric isomers, their salts, their solvates such as hydrates, and their mixtures: H2N—T—NH2 (II) Formula (II) wherein T represents a divalent hydrocarbon group, linear or branched, saturated or unsaturated, preferably saturated, comprising from 4 to 22 carbon atoms, optionally substituted by an -NH2 group, the T group being substituted by one or more hydroxyl (-OH) groups and / or interrupted by one or more groups selected from -C(O)-, -NRa- or their combinations such as -NRa-C(O)- or -C(O)-NRa-, with Ra representing a hydrogen atom or a (CrC4)alkyl group; and iii) optionally one or more coloring agents selected from pigments, direct dyes, and mixtures thereof, preferably from pigments.

[0010] According to a second aspect, the present invention relates to a composition (C) comprising the compound(s) A as defined above, the polyamine compound(s) B as defined above and optionally one or more coloring agents chosen from pigments, direct dyes, and their mixtures, preferably from pigments.

[0011] According to a third aspect, the present invention relates to a two- or three-compartment device comprising: - a first compartment containing a composition (A) comprising the compound(s) (A) as defined above and possibly one or more coloring agents chosen from pigments, direct dyes, and their mixtures, preferably from pigments; - a second compartment separate from the first compartment containing a composition (B) comprising the polyamine compound(s) B as defined above and optionally one or more coloring agents selected from pigments, direct dyes, and mixtures thereof, preferably from pigments; and - optionally a third compartment separate from the first and second compartments containing a composition comprising one or more coloring agents selected from pigments, direct dyes, and mixtures thereof, preferably from pigments.

[0012] According to a fourth aspect, the present invention relates to the use of one or more compounds A as defined above associated with one or more polyamine compounds B as defined above or of a composition (C) comprising the compound(s) A as defined above and the polyamine compound(s) B as defined above, for the relaxation of curls and / or the smoothing of keratin fibers.

[0013] According to a fifth aspect, the present invention relates to the use of one or more compounds A as defined above associated with one or more polyamine compounds B as defined above and with one or more coloring agents selected from pigments, direct dyes, and mixtures thereof, preferably from pigments or of a composition (C) comprising the compound(s) A as defined above, the polyamine compound(s) B as defined above and the coloring agent(s) selected from pigments, direct dyes, and mixtures thereof, for the coloring of keratin fibers. Detailed description of the invention

[0014] For the purposes of the present invention, and unless otherwise indicated:

[0015] ■ By "keratin fibers" we mean fibers of human or animal origin such as such as hair, body hair, eyelashes, eyebrows, wool, angora, cashmere or fur. According to the present invention, the keratin fibers are preferably human keratin fibers, more preferably hair;

[0016] ■ 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;

[0017] ■ 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; ■ by "(hetero)aryl" we mean the aryl or heteroaryl groups;

[0018] ■ by "(hetero)cycloalkyl" means cycloalkyl or heterocycloalkyl groups;

[0019] ■ the "aryl" or "heteroaryl" radicals or the aryl or heteroaryl part of a radical can be substituted by at least one substituent attached to a carbon atom, chosen from: - a (poly)(hydroxy)alkyl radical in CrC6, preferably in Ci-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 CrC4 and the radical R' is an alkyl radical in CrC4; a carbamoyl radical (R2N-C(O)-) in which the radicals R, 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, a Ci-C4 alkyl radical and the radical R' represents a C1-C4 alkyl radical, 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 CrC4; - 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); ■ 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, (poly)hydroxy C2-C4 alkoxy; - alkylearbonylamino (RC(O)-NR'-) in which the radical R' is a hydrogen atom, an alkyl radical in Ci-C4 and the radical R is an alkyl radical in CrC4, amino substituted by one or two identical or different alkyl groups in CrC4; - alkylearbonyloxy (RC(O)-O-) in which the radical R is an alkyl radical in CrC4, amino substituted by one or two identical or different alkyl groups in CrC4; - alkoxycarbonyl (RO-C(O)-) in which the radical R is an alkyl radical in CrC4;

[0020] ■ 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;

[0021] ■ 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;

[0022] ■ A "cyclic" or "cycloalkyl" radical is a non-cyclic hydrocarbon radical aromatic, mono or polycyclic, condensed or not, containing from 5 to 14 carbon atoms, which may have from 1 to several unsaturations, preferably the cycloalkyl is a cyclohexyl group;

[0023] ■ 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;

[0024] ■ an "alkyl" radical is a saturated hydrocarbon radical, linear or branched, in particularly in Ci-C6, preferably in CrC4;

[0025] ■ an "(Cx-Cy) alkyl group" is an alkyl radical comprising x to y atoms of carbon;

[0026] ■ an "alkylene group" is a divalent hydrocarbon radical, linear or branched, saturated;

[0027] ■ a "(Cx-Cy)alkylene group" is an alkylene group comprising from x' to y' atoms of carbon;

[0028] ■ 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;

[0029] ■ a "(poly)(hydroxy)alkyl" radical designates a Ci-C6 alkyl radical, of preferably in Ci-C4 possibly substituted by one or more hydroxy radicals, preferably substituted by 1 to 4 hydroxy groups, more particularly between 1 and 3;

[0030] ■ 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;

[0031] ■ By "monosaccharide", we mean a monosaccharide sugar comprising at least 5 carbon atoms in particular 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;

[0032] ■ By "disaccharide", we mean a disaccharide sugar which is a compound made up of two sugars linked together by O-glycosidic bonds said compounds being made up of two monosaccharides (also called mono-glycosidics) as defined above said monosaccharide units comprising at least 5 carbon atoms, preferably 6, particularly the monosaccharide units being 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; more specifically, it concerns compounds 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;

[0033] ■ By "polysaccharide", we mean a polysaccharide sugar which is a compound consisting of at least 3 monosaccharides linked together by O-glycosidic bonds, said polymers being composed of monosaccharide units (also called mono-glycosidic units) as defined above, said monosaccharide units comprising at least 5 carbon atoms, preferably 6, particularly the units monosaccharides 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 particularly it concerns compounds formed of 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 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, and w is an integer greater than or equal to 2, particularly inclusively between 3 and 3000, more particularly between 5 and 2500, preferably between 10 and 2300, particularly inclusively between 15 and 1000, more particularly between 20 and 500, preferably between 25 and 200;

[0034] ■ By "salt", we mean an addition salt with an organic acid or base ormineral. The addition salts with an organic or mineral acid are in particular chosen from the salts derived i) from hydrochloric acid HCl, ii) from hydrobromic acid HBr, iii) from sulfuric acid H2SO4, iv) from alkylsulfonic acids: Alk-S(O)2OH such as methylsulfonic acid and ethylsulfonic acid; v) from arylsulfonic acids: Ar-S(O)2OH such as benzenesulfonic acid and toluenesulfonic acid; vi) from alkoxysulfinic acids: Alk-OS(O)OH such as methoxysulfinic acid and ethoxysulfinic acid; vii) from aryloxysulfinic acids such as tolueneoxysulfinic acid and phenoxysulfinic acid; viii) from phosphoric acid H3PO4; ix) of triflic acid CF3SO3H and x) of tetrafluoroboric acid HBF4;xi) of carboxylic organic 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 as 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 the 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 the 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. Addition salts with an organic or mineral base are in particular chosen addition salts with an organic or mineral base such as alkali metal hydroxides, alkaline earth metal hydroxides, alkali or alkaline- metal carbonates; earthy, alkali or alkaline-earth metal bicarbonates, addition salts with so-called basic amino acids such as arginine, lysine, addition salts with possibly hydroxylated amines;

[0035] ■ the "solvates" represent the hydrates as well as the association with alcohols linear or branched C1-C4 linear or branched such as ethanol, isopropanol, n-propanol; ■ by "reducing agent" we mean an agent capable of reducing the disulfide bonds of hair, such as compounds chosen from among thiols, alkali sulfites, hydrides and phosphines;

[0036] The expressions "at least one" and "one or more" are synonymous and can be used interchangeably.

[0037] The expressions "between ... and ...", "includes from ... to ...", "made up of ... to ...", and "ranging from ... to ..." should be understood inclusive of bounds, unless otherwise specified. Keratin fiber processing method

[0038] According to a first aspect, the present invention relates to a process for treating keratin fibers as defined above. Compounds A

[0039] The compound(s) A used in the treatment process according to the present invention are chosen from compounds of formula (I) and / or (!'), their optical isomers, their geometric isomers, their salts, their solvates such as hydrates, and their mixtures.

[0040] According to a preferred embodiment, the compound(s) A are chosen from compounds of formula (I), their optical isomers, their geometric isomers, their solvates such as hydrates, and their mixtures, 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 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.

[0041] According to a preferred embodiment, a (hetero)cycle designates a heterocyclic divalent radical (i.e. a heterocycle), 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).

[0042] According to a preferred embodiment, 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-.

[0043] According to a first preferred embodiment, the compound(s) A are chosen from the compounds of formula (I), their optical isomers, their geometric isomers, their solvates such as hydrates, and their mixtures, such as: - 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 being possibly 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 of formula (I) contain at least 2 radicals -C(O)-C(Ra)(Rb)-C(O)-R4.

[0044] According to a preferred embodiment, AK2 represents a linear or branched monovalent hydrocarbon chain, saturated or unsaturated, in Ci2-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-.

[0045] According to this first preferred embodiment, the compound(s) A are preferably chosen from the following compounds (1), (2), (3), (4), (7), (8), (9), (11) and (16), their optical isomers, their geometric isomers, their solvates such as hydrates, and their mixtures: (1) (3) OO (11)

[0046] According to this first preferred embodiment, the compound(s) A are more preferably chosen from among compound (16), its optical isomers, its geometric isomers, its solvates such as hydrates, and their mixtures.

[0047] According to a second embodiment, the compound(s) A are chosen from the compounds of formula (I), their optical isomers, their geometric isomers, their solvates such as hydrates, and their mixtures, 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);

[0048] it being understood that the compounds of formula (I) contain at least 2 radicals -C(O)-C(Ra)(Rb)-C(O)-R4. According to this second embodiment, the compound(s) A are preferably chosen from compounds (5) and (6) below, their optical isomers, their geometric isomers, their solvates such as hydrates, and their mixtures: (6).

[0049] According to a third embodiment, the compound(s) A are chosen from the compounds of formula (I), their optical isomers, their geometric isomers, their solvates such as hydrates, and their mixtures, such as: - 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 Ci2-C24, preferably in Ci6-C20, in particular Ci8, 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 substituted by one or more radicals -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 -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 Ci-C6, 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 the compounds of formula (I) contain at least 2 radicals -C(O)-C(Ra)(Rb)-C(O)-R4.

[0050] According to a preferred embodiment, m is equal to 3, n is equal to 1 and u is equal to 1.

[0051] According to a preferred embodiment, t is equal to 0.

[0052] According to a preferred embodiment, q is equal to 0.

[0053] According to a preferred embodiment, Y denotes -C(O)-O.

[0054] According to a preferred embodiment, none of the AK2 radicals are interrupted.

[0055] According to a preferred embodiment, the AK2 radicals are saturated.

[0056] According to a preferred embodiment, the AK2 radicals are not substituted by - GOLD.

[0057] According to a preferred embodiment, AK3 represents a linear or branched divalent hydrocarbon chain saturated or unsaturated in Ci-C6, more preferably saturated in Ci-C6, even more preferably saturated in C1-C4, better saturated in C3.

[0058] According to this third embodiment, the compound(s) A are in particular chosen from the compounds (10) below, their optical isomers, their geometric isomers, their solvates such as hydrates, and their mixtures:

[0059] According to a fourth embodiment, the compound(s) A are chosen from compounds of formula (I), their optical isomers, their geometric isomers, their solvates such as hydrates, and their mixtures, such as: - p is equal to 1; - Z represents a multivalent hydrocarbon radical in C2 to C24, particularly in C4 to C20, preferably in C5 or 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 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 the compounds of formula (I) contain at least 2 radicals C(O)-C(Ra)(Rb)-C(O)-R4.

[0060] According to a preferred embodiment, n is equal to 0 and m is equal to 1.

[0061] According to a preferred embodiment, Z is a divalent radical.

[0062] According to a preferred embodiment, if Z is an unsaturated chain, AK2 is a unsaturated chain, and if Z is a saturated chain, AK2 is a saturated chain.

[0063] According to this fourth embodiment, the compound(s) A are in particular chosen from the compounds of formula (lie), their optical isomers, their geometric isomers, their solvates such as hydrates, and their mixtures: HZY-AK4-Y'-ZH (lie) formula (lie) 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 C20, 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.

[0064] According to this fourth embodiment, the compound(s) A are in particular chosen from compounds (12) and (15) below, their optical isomers, their geometric isomers, their solvates such as hydrates, and their mixtures: (12)

[0065] According to this fourth embodiment, the compound(s) A are more particularly chosen from compound (15), its optical isomers, its geometric isomers, their salts, their solvates such as hydrates, and their mixtures.

[0066] According to a fifth embodiment, the compound(s) A are chosen from the compounds of formula (I), their optical isomers, their geometric isomers, their solvates such as hydrates, and their mixtures, 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 Ci6 to C24, preferably in Cp, said chain being 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 -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)- 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 the compounds of formula (I) contain at least 2 radicals C(O)-C(Ra)(Rb)-C(O)-R4.

[0067] According to a preferred embodiment, t is equal to 0 and u is equal to 1.

[0068] According to a preferred embodiment, all AK2 radicals are identical, and Preference is given that all Y radicals are identical.

[0069] According to a preferred embodiment, Y denotes -OC(O)-.

[0070] According to a particular embodiment, the compounds according to this fifth variant are in particular chosen from compounds of formula (lid), their optical isomers, their geometric isomers, their solvates such as hydrates, and their mixtures: [AK'2-OCO-CH2]3-C-CH2-OC(O)-C(Ra)(Rb)-C(O)-R4 (lid) formula (lid) in which: - AK'2 represents a linear or branched monovalent hydrocarbon chain, preferably linear, saturated or unsaturated, preferably saturated, in Ci4-C30, preferably in Ci6-C24, preferably in Cp, said chain being substituted by one or more identical or different radicals chosen 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 previously for formula (I); it being understood that the said compounds contain at least 2 C(O)-C(Ra)(Rb)-C(O)-R4 radicals.

[0071] According to a sixth embodiment, the compound(s) A are chosen from compounds of formula (I), their optical isomers, their geometric isomers, their solvates such as hydrates, and their mixtures, such as: - 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 C[4-C24, preferably in C15, 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)cycles, 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; - 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 the compounds of formula (I) contain at least 2 C(O)-C(Ra)(Rb)-C(O)-R4 radicals.

[0072] According to a preferred embodiment, in this variant, 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 a number integer between 1 and 3, preferably 1, (heterocycle) designates 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 previously for formula (I), and in particular -OH or -OC(O)-C(Ra)(Rb )-C(O)-R4).

[0073] According to this sixth embodiment, the compound(s) A are in particular chosen from the compounds of formula (link), their optical isomers, their geometric isomers, their solvates such as hydrates, and their mixtures: 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, preferably in Ci5, said chain being optionally substituted by one or more identical or different radicals selected from -OH, -OC(O)-C(Ra)(Rb)-C(O)-R 4) and -S-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 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 optionally interrupted by -OC(O)- or -C(O)-O-, and more preferably being uninterrupted; it being understood that the compounds of formula (lie) contain at least 2 radicals -C(O)-C(Ra)(Rb)-C(O)-R4.

[0074] According to this sixth embodiment, the compound(s) A are in particular chosen from the compounds (14) below, their optical isomers, their geometric isomers, their solvates such as hydrates, and their mixtures: (14) 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.

[0075] Preferably, the compound(s) A are chosen from the compounds of formula (la), their optical isomers, their geometric isomers, their solvates such as hydrates, and their mixtures: 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 for formula (I), preferably Y denotes -OC(O); it being understood that the compounds of formula (la) contain at least 2 radicals C(O)-C(Ra)(Rb)-C(O)-R4.

[0076] Preferably, the compound(s) A are chosen from compounds of formula (Ib), their optical isomers, their geometric isomers, their solvates such as hydrates, and their mixtures: 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 previously for 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 Ci2-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-(O-C(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 for formula (I), preferably v is equal to 2; - X is such as defined previously for formula (I), preferably X denotes a sulfur atom; - Y, AK1, t, q, u, R, R4, Ra and Rb being such as defined previously for formula (i); it being understood that the compounds of formula (Ib) contain at least 2 radicals -C(O)-C(Ra)(Rb)-C(O)-R4.

[0077] Preferably, the compound(s) A are chosen from compounds of formula (the), their optical isomers, their geometric isomers, their solvates such as hydrates, and their mixtures: 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 possibly substituted by one or more radicals -[(O) t-(AKl)q-(O-C(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 C2o-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 for formula (I), and 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 the compounds of formula (le) contain at least 2 radicals -C(O)-C(Ra)(Rb)-C(O)-R4.

[0078] Preferably, the compound(s) A are chosen from compounds of formula (Id), their optical isomers, their geometric isomers, their solvates such as hydrates, and their mixtures: 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 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 previously for formula (I), preferably X designates a sulfur atom; Y, AK1, AK3, v, R, IC, Ra and Rb being as defined previously for formula (I), it being understood that the compounds of formula (Id) contain at least 2 radicals -C(O)-C(Ra)(Rb)-C(O)-R4.

[0079] Preferably, the compound(s) A are chosen from compounds of formula (the), their optical isomers, their geometric isomers, their solvates such as hydrates, and their mixtures: 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 previously for formula (I), preferably n is zero; - Z represents a divalent hydrocarbon radical in C2 to C24, in particular in C3 to C12, 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 selected 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 (ia heterocycle), preferably a heterocycloalkyl radical, more particularly a divalent heterocycloalkyl radical comprising 5 or 6 links, in particular a divalent tetrahydrofuran radical or a divalent tetrahydropyran radical, said heterocycle being optionally substituted by one or more 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); . - 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-ROv, 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 for formula (I), 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 the compounds of formula (le) contain at least 2 radicals C(O)-C(Ra)(Rb)-C(O)-R4.

[0080] According to a preferred embodiment, the compound(s) A are chosen from the following compounds (1) to (16), their optical isomers, their geometric isomers, their solvates such as hydrates, and their mixtures: (5) (16) 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.

[0081] According to a more preferred embodiment, the compound(s) A are chosen from compounds (15), (16), their optical isomers, their geometric isomers, their solvates such as hydrates, and their mixtures.

[0082] According to a preferred embodiment, the compound(s) A are chosen from compounds of formula (!'), their optical isomers, their geometric isomers, their salts, their solvates such as hydrates, and their mixtures.

[0083] Preferably, the compound(s) A are chosen from compounds of formula (l'a), their optical isomers, their geometric isomers, their salts, their solvates such as hydrates, and their mixtures: (there) Formula (l'a) in which: - R1 is as defined previously for the formula (!'), particularly represents a versatile hydrocarbon radical in C2 to CM, preferably in C3-C12, preferably in C4-C10, linear or branched, saturated or unsaturated, conjugated or not, acyclic or cyclic, aromatic or not, R1 being further: a) possibly substituted by one or more hydroxy groups OH, and / or b) possibly interrupted by one or more heteroatoms or groups chosen from O, S, -N(R'), preferably interrupted by one or more oxygen atoms in which R' is as defined previously for the formula (!'); - R2 is as defined previously for the formula (!'), preferably R2 represents a (Ci-C6)alkyl group, linear or branched, preferably a (Ci-C4)alkyl group, more preferably methyl or tert-butyl such as methyl; and - n is as defined previously for the formula (!'), preferably n denotes an integer from 2 to 9.

[0084] According to one embodiment, the compounds of formula (!') or (l'a) are such that R1 represents a C6-C8, linear or branched, unsaturated monocyclic or bicyclic, preferably monocyclic, possibly aromatic hydrocarbon polymorphic radical such as phenyl.

[0085] According to another embodiment, the compounds of formula (!') or (a) are such that R1 represents a C5 to C12 saturated monocyclic or bicyclic hydrocarbon polyvalent radical, optionally interrupted by one or more heteroatoms or groups selected from O, S, -N(R'), in which R' represents a hydrogen atom, an alkyl group having from 1 to 4 carbon atoms, preferably interrupted by one or more oxygen atoms. Preferably, according to this other embodiment, R1 represents a monosaccharide or polysaccharide motif, in particular a disaccharide, on which n hydroxyl groups have been substituted by n -OC(O)-CH2-C(O)-R2 groups with R2 and n as defined above for formula (!') or (a).

[0086] Suitable monosaccharides according to the invention include, but are not limited to, ribose, glucose, mannose, galactose, fructose, sorbose and inositol.

[0087] According to one embodiment, the disaccharides are selected from cellobiose, maltose, lactose, raffinose, sucrose, trehalose, melibiulose, melibiose, mannobiose, kojibiose, nigerose, isomaltose, rutinose, rutinulose, xylobiose, preferably sucrose.

[0088] According to another preferred embodiment of the invention, the compounds of formula (!') or (l'a) are such that R1 represents a C2-Ci2, preferably C3-Ci0, linear or branched, saturated or unsaturated, preferably saturated, acyclic hydrocarbon polyvalent radical.

[0089] Preferably, the compounds of formula (I) or (la) are such that R1 represents a versatile acyclic hydrocarbon radical, selected from the radicals mannitol, xylitol, sorbitol, trimethylolpropane, di(trimethylolpropane), 2-methyl-1,3-propanediol, 2-hydroxymethyl-1,3-propanediol, 2,2-dimethyl-1,3-propanediol, erythritol, pentaerythritol or dipentaerythritol, more preferably mannitol, xylitol, sorbitol, trimethylolpropane, di(trimethylolpropane), 2-methyl-1,3-propanediol, 2-hydroxymethyl-1,3-propanediol, erythritol, pentaerythritol or dipentaerythritol.

[0090] According to a particular embodiment of the invention, the compounds of formula (!') or (l'a) are such that n denotes an integer from 2 to 9, more particularly n denotes an integer from 3 to 9, even more particularly n denotes an integer from 4 to 9 such as 6 or 8.

[0091] According to one embodiment, the compounds of formula (!') or (l'a) are such that n equals 2. According to another embodiment, the compounds of formula (!') or (l'a) are such that n equals 3. According to another embodiment, the compounds of formula (!') or (l'a) are such that n equals 4. According to another embodiment, the compounds of formula (!') or (l'a) are such that n equals 5. According to another embodiment, the compounds of formula (!') or (l'a) are such that n equals 6. According to another embodiment, the compounds of formula (I) or (la) are such that n equals 7. According to another embodiment, the compounds of formula (I) or (la) are such that n equals 8. According to another embodiment, the compounds of formula (I) or (la) are such that n equals 9.

[0092] Preferably, the compound(s) A are chosen from the following compounds, their optical isomers, their salts, their solvates such as hydrates, and their mixtures: (Compound) CAS No. Chemical Name Chemical Structure (l'J 700S65-73-2 3-oxo-l 1-(1,7-heptanediyl) butaroic acid ester JL A .AA 632336-20-0 3-oxo-l-(1,8-odanedM) butanoic acid ester .'■■''A ..■••'“X. ..•■■'''■v. .-'''A VV A';''' •X^- VX--''- X>Z x<'' èl 501426-98-8 3-oxo-ll-(lW-decanediyl) butanoic acid ester v ''X<-''' Xv-' -X'''' Xx.-''hanediyl ester d’acide butanoïque A A A x, ^x x^ x0-- X^x 5 G 0 (S? 145020-19-5 3-oxa-2-butyt-2-éthy§-1,3-propanediyl ester d'acide butanoique Ax x XJ- x-' (7’) 87530-36-7 3-oxo-112,2- fêtramethyi-12-éthanediyi ester d'acide butanoïque ' : t 'X ■ / X ' xxX X^x -X xï;X X^' / X; H il (8’) 58213-75-5 3-oxo-1.1-(1 -méthyl 1,3-propanediyl) ester d'acide butanoïque X‘A}A X "A, / A;.^x- A^X Ax . (compound) mcw Chemical name Chemical structure (*') 58213-74-4 3^x0-11'42,2-dmethylM-(1-methylethyl)-! 3-propanediyl ester of butanoic acid / \ / \ 39564-28-8 3-oxo-l cT-0J> pentanediyl!) ester of butanic acid VX^- a<>' (1T) 14276-67-6 3-oxo-1,142,2-dimethylM.S-propanediyl) ester of butanoic acid / v (12!| 13018-41-2 3-oxo-1,4-butanoediyl ester of butanoic acid x'v"' Xv>f" 6079-90-9 3-oxo-1 -mêthyî-1,2-ethanediyl ester of butanoic acid --^-4 6 Ô 04') 5459-04-1 3-oxo-l 52-ethanediyl butanoic acid ester X? v? (15'} 2388-18-3 3-oxo-l ,T-(1,6-hexanediyl) ester d: butanoic acid 3oxo-1,6-hexanediyl ester of butanoic acid (9Ci) X3 (Compound^ CAS Name each Chemical Structure 32818-60-3 bis(3-oxobutamate) of V'-P^-BHCtS-djoxoMoxy)methyl-1,3-propanediyO __ / ■''V V'^'* V Vx -■'V on 51980-20-2 bis(3-oxübutarôate) detl42;2- Bis(hydroxymêth^ )-1,3-propanecOy(] 0 Ü | 1 SH / Gf n to o (181 X A. / ' ' ¥ < ' H h G 0 (19') 130973-05-6 3-oxo-1,3,5-benzenetriyl ester of butanoic acid 0 G ¥ X $ 9 'SZ' Sif \y "s^ S, (29') 139264-86-1 3-oxq-1,2.4-benzeretriyl butanoic acid ester X X'-' I 1 JJ 1 IL (Compound) H'CAS- Chthmic name (2T) 22208-25-9 Trimethylpropane treatment K-FLEX 7301 \ 4^' :.........A. GO (22') 2360524-48- SI X;' c-" Xx.<- -3-ôXo-. 1142,2-^3(((4,4-dmethyM,3-dMXGpeniyl)exy|meth yO-13-propanediyO pentanoic acid ester. OOO <> Jk Jk.aa.. JL. jL .-• „yy g- -- x (Compose) itcas Name etching : chemical (26') teîra-acefoacetate of meso-etyÈhdW | Same JL. Cf OF""© y» / Q.™ / CF^.0 (27") 169533-29-3 aDG^copyranose, oxoMaoaate) (28') 2254710-55- 7 5-ammo-2-[(2.3,4-te-O-(1,3-dioxobuty^-D-xyfopyranosyOoxyj-d'adde benzoïque >$ ;-F' ^0'' (29') 1236300-10-10- 9 2,3,4f6-oteopyro)decopyrao3 a 1,3,4,6-tetrax-O-(1,3-dioxobutyiyp-D-frudofuranosyl, ^->kV "^y" ? î? . ■■■■ Av ,.AV -A--3⁄4.....xy T ! 1 \x (Composed) ■HW' . Strudisre:^ (3Ô'| D-Qucopyranose. 96481-26-4 pentacîs(3-oxobutanoate) V* ' v A (3V) D-GlmtoL, 14:3,6- # A 944473:12-5 diahhydra-ate- 2 r4vjno x(3) ,■* (32') 2254710-49- 9 .Xfi Y Jx (33') hexa-aceïoacetate of 7-X sorbitot Z0 0 IIXXX .& ' ' * ° rj " z 4 -X ..-.&" .0 .-û Ox. $•■' 6 ox X' ô (Compound) ras Chemical name^ Strtætae chsrrà^ (34'| D-Gksdtoi, 4-OgD- R: 2T6756-89-7 gaiactepyranosyk 0' Ç ™R1 poivacetoacetate H ”......5.......\ / ........\ 7......* y— / J ” ) \ \. with RI chosen; among -C(0)-CHî-C(Q)-Œ H with at least two radicals R1 represent - C (O )-C Hs-C (O )-C Ha (35-) Sucrose, 101655-52-1 poivacetoacetate / -s. ir\ v\ / *1 \ / with RI chosen from -C(O)-CH2-C(O)-CHss H with at least two radicals RI represent -C(O)-CHs-C(O)-CH3 (36') Glucose RI m A ''Vi \ / \ r^8«4 b Cr Q ✓ (Cornposé J CAS Nçm chemical Structure cM {37"> Mannose polyacetoacetate MY (38'> XyKof polyacetoacetate ^z 2 ) s, / 01W *S w .—4 (3S1 Sorbital polyacetoacetate Pt Ri I 1 0 Yi s' 0 0 RY preferably 6 RI radicals represent -C(O)-CH^G(O)-CH3 (40') RI XQ GX f * RI 0 Y three RI radicals represent -C(O)-CH2-C(O)-CH3 ; and three RI radicals represent a hydrogen atom (Compound) CAS No.? Chemical Name? Chemical sfractwë (4T) 1471-94-9 0 G .Xx, X^x, X'xX x^\ Z\ XX XZ X-^ X- "y HGG (421 2552-36-5 yZ V' JH xx\ Z\ Z\. 139614-56-5 1.1J.. .1 --- x^ V x H .H (441 96169-30-1 (451 75639-01-9 Ci <^x i'-x. ^x -“'x --"$X --"x (461 Dipentaerythritoi polyacetoacetafel a" ^1—-XJ / A preferably 5 or 6 radicals RI f more preferential meut 6 radicals RI represent -C(O)-CH2-C(O)-CHî in which identical or different RIs represent a hydrogen atom or a -C(O)-CH2-C(O)-CH3 group, it being understood that at least two RI radicals represent -C(O)-CH2-C(O)-CH3, preferably at least three RI radicals represent -C(O)-CH2-C(O)-CH3.

[0093] More preferably, the compound(s) A are chosen from compounds (16'), (18'), (21'), (35'), (36'), (37'), (38'), (39'), (40') and (46'), their optical isomers, their salts, their solvates such as hydrates, and their mixtures.

[0094] Even more preferably, the compound(s) A are chosen from compounds (16'), (21'), (35'), (38'), (39') and (46'), their optical isomers, their salts, their solvates such as hydrates, and their mixtures.

[0095] Most preferably, the compound(s) A are chosen from compounds (16'), (35') and (46'), their optical isomers, their salts, their solvates such as hydrates, and their mixtures. Preparation of compounds of formula (I)

[0096] 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

[0097] 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: (H)pZ(OH)m +mR'C0-AK'2 -> (H)pZ(OH)m,m(YAK'2)m diagram in which: - Y represents -OC(O)- ; - R' designating in particular -OH or -Cl; preferably R' designates -OH; - AK'2 represents a linear or branched, unsaturated hydrocarbon chain, in Ci-C 40, 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.

[0098] According to a preferred embodiment, m is equal to m'.

[0099] Polyols (H)pZ(OH)m can be cyclic or acyclic.

[0100] Examples of cyclic (H)pZ(OH)m polyols include maltose, lactose, raffinose, sucrose, trehalose, melibiulose, melibiose, mannobiose, kojibiose, nigerose, isomaltose, rutinose, rutinulose, xylobiose or sorbitan.

[0101] 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.

[0102] 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.

[0103] 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.

[0104] Monounsaturated fatty acids are in particular selected from palmitoleic acid, oleic acid, 9-eicosenoic acid, 11-eicosenoic acid, erucic acid and nervonic acid.

[0105] 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.

[0106] More preferably, the unsaturated fatty acid is chosen from ricinoleic acid, oleic acid, palmitoleic acid, erucic acid and mixtures thereof. Second stage

[0107] 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.

[0108] 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 an integer from 1 to 12, preferably from 1 to 6, such as 2-mercaptoethanol, 3-mercapto-1-propanol, 6-mercapto-1-hexanol, 4-mercapto-1-butanol, or such as branched hydroxylated thiols having preferably from 1 to 6 carbon atoms, such as 3-mercapto-3-methylbutanol, 3-mercapto-2-butanol, or such as thiols polyhydroxylated, preferably comprising 1 to 6 carbon atoms such as 3-mercapto-1,2 propanediol HS-CH(OH)-CH2OH.

[0109] The compounds (IV) obtained are thus substituted by a radical -S-AK3-(OH)V with v being equal to 1 if the thiol is hydroxylated and v being 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

[0110] 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 the 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 the compounds (Illii), such as compound bl illustrated in the diagram below.

[0111] 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.

[0112] 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

[0113] 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.

[0114] According to a preferred embodiment, Gp-C(0)-C(Ra)(Rb)-C(0)-R4 designates an ester selected from ethyl acetoacetate, ethyl 2-methylacetoacetate, ter-butyl acetoacetate, preferably ter-butyl acetoacetate.

[0115] Structural compounds (la), (le), such as structural compounds (lie), structural compounds (Id) and (le) can be obtained according to this process.

[0116] 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:

[0117] In some cases, the compounds (H)pZ(OH)mm (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 denoting -CH2-CH-CH2-, are commercially available. 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.

[0118] 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, 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): Composed of 3 Compound b3

[0119] 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.

[0120] 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

[0121] 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

[0122] The compounds of formula (la) to (le) can further be prepared by the following series of reactions:

[0123] - 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 previously, under conditions known to those skilled in the art to form an ester bond Y according to the scheme below: (H)pZ(COOH)m+mH0-AK'2 -> (H)pZ(COOH)m_m(YAK'2)m 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.

[0124] According to a preferred embodiment, m is equal to m'.

[0125] Polyacids (H)pZ(OH)m can be cyclic or acyclic.

[0126] Polyacids may preferably designate dicarboxylic acids possibly hydroxylated, tricarboxylic acids possibly hydroxylated, tetraboxylic acids possibly hydroxylated.

[0127] 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.

[0128] 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.

[0129] 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.

[0130] 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).

[0131] 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.

[0132] Fatty alcohols HO-AK'2 can be mono or polyunsaturated (presence of one or more ethylenic double bonds).

[0133] HO-AK'2 fatty alcohols may contain several alcohol functions.

[0134] 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.

[0135] Polyunsaturated fatty alcohols are in particular selected 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).

[0136] According to a preferred embodiment, the fatty alcohol HO-AK'2 is selected from oleyl alcohol, linoleic alcohol (Linoleyl alcohol) or mixtures thereof.

[0137] The following steps are identical to those described previously:

[0138] - 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.

[0139] - 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.

[0140] - 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.

[0141] 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.

[0142] 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

[0143] 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

[0144] 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:

[0145] Compound 36 Compound b6 Compound b6 Compound e6 Preparation of compounds of formula (!') The compounds of formula (!') can be obtained by (poly)condensation(s) of n equivalents of dicarbonyl reagent with a nucleophilic reagent R'(XH)n comprising n equivalents of -XH nucleophilic functions according to the following scheme:

[0146]

[0147] Diagram in which: - R1, R2, Ra, Rb and n are such as defined for the compound of formula (!'); - R3 represents a hydrogen atom, an (Ci-C4)alkyl group such as methyl, ethyl, isobutyl, t-butyl, or an electrofuge group such as CHal3, or Hal3C-SO2- as triflate, with Hal, identical or different, representing a halogen atom; and - X' represents an oxygen atom, or sulfur, preferably O. These (poly)condensation methods are known to those skilled in the art, for example “From rigid and flexible foams to elastomers via Michael addition chemistry”, Polymer, 106, 128-139, (2016), “Dynamic Curing Agents for Amine-Hardened Epoxy Vitrimers with Short (Re)processing Times”, Macromolecules, 53(7), 2485-2495 (2020), “Super photo-base initiated organic-inorganic hybrid coatings by plural-cure mechanisms”, Progress in Organic Coatings, 127, 222-230 (2019) or patent application PL159100: Method for manufacturing acetylacetate esters.

[0148] According to a particular embodiment of the invention, R'(XH)n is selected from the acyclic polyols R'(OH)n, in particular selected from glycerol, trimethylolpropane, ethylene glycol, diethylene glycol, triethylene glycol, tetraethylene glycol, propylene glycol, dipropylene glycol, butylene glycol, trimethylolethane, pentamethylene glycol, trimethylpentanediol, pentyl glycol, isosorbide, pentaerythritol, dipentaerythritol, hexamethylene glycol, hexylene glycol, hexandediol, neopentyl glycol, 1,2-propanediol; 1,3-propanediol; 1,2-butanediol, 1,3-butanediol, 2,3-butanediol, 1,4-butanediol; 2,4-butanediol, 3,4-butanediol; 1,4-Pentanediol; 1,5-pentanediol, 2,2,4-Trimethyl-l,3-pentanediol, 1,6-hexanediol, 1,2 octanediol, 1,8 octane diol, 1,10-decanediol, 2-methyl-l,3-propane diol, hexylene glycol, isoprene glycol.

[0149] According to one variant, R'(XH)n is chosen from among the cyclic polyols R'(OH)n in particular chosen from among the monosaccharides and disaccharides, as defined above, alone or in mixture.

[0150] Preferably, R'(XH)n is chosen from the polyols R'(OH)n alone or in mixtures in particular from mannitol, xylitol, sorbitol, glycerol, glucose, trimethylolethane, trimethylolpropane, di(trimethylolpropane), 2-methyl-1,3-propanediol, 2-hydroxymethyl-1,3-propanediol, 2,2-dimethyl-1,3-propanediol, 1' erythritol, pentaerythritol, dipentaerythritol, and mixtures thereof, more particularly from trimethylolethane, trimethylolpropane, erythritol, pentaerythritol, glycerol, glucose, sucrose and sorbitol, and mixtures thereof.

[0151] According to another embodiment, R'(XH)n is selected from among the diamines R'(NH2)2 in particular the hydroxyalkylated aliphatic diamines such as ro,o'-bis(diethanolaminomethyl)-p-nonylphenol, N,N,N,N'-tetra(2-hydroxypropyl)ethylenediamine (Quadrol L, available from BASF) and N,N,N,N-tetra(2-hydroxyethyl)ethylenediamine, and mixtures thereof.

[0152] According to another advantageous embodiment, the compound(s) of formula (!') or (l'a) are obtained by (poly)condensation(s) of n equivalents of propylenedioxy carbonyl reagent with a polyamine nucleophilic reagent R'(NH2)n comprising n equivalents of -NH2 nucleophilic functions according to the following scheme: Diagram in which: - R1, R2, Ra, and n are such as defined for the compound of formula (!'); - R'-NH2 is notably chosen from among ethylenediamine, 1,3-diaminopropane, cadaverine, hexamethylenediamine, 1,2-diaminopropane, 1,2-diaminocyclohexane, phenylenediamine; and - Rb and Rc', whether identical or different, represent a hydrogen atom and a (CrC4)alkyl group.

[0153] This type of synthesis process is known to those skilled in the art; for example, "Acetoacetylation with 2,2,6-trimethyl-4H-l,3-dioxin-4-one: a convenient alternative to diketene", Journal of Organic Chemistry, 50(14), 2431-5, (1985) or "Synthesis of new Biginelli polycondensates: renewable materials with tunable high glass transition temperatures", Polymer International, 70(5), 506-513 (2021).

[0154] According to another advantageous embodiment, the compounds of formula (!') or (l'a) are obtained by (poly)condensation(s) of n equivalents of diketene reagent with a nucleophilic reagent R*(X)n comprising n equivalents of -XH nucleophilic functions according to the following scheme: Diagram in which: - R1, and n are such that defined for the compound of formula (!'); and

[0155] - X' represents an oxygen atom, or sulfur atom, or N(R') with R'=H.

[0156] This type of process is known to those skilled in the art. For example, one might cite “Acetoacetamides, 2-hydroximinoacetoacetamides, and 2,3-bis(hydroximino)-butyramides”, Journal fur P raktische Chemie (Leipzig), 323(2), 337-44, (1981) or Angewandte Makromolekulare Chemie, 9, 96-105, (1969). Polyamine compounds B

[0157] The polyamine compound(s) B used in the process according to the present invention are chosen from the compounds of formula (II), their optical isomers, their geometric isomers, their salts, their solvates such as hydrates, and their mixtures: H2N—T—NH2 (II) Formula (II) in which T represents a divalent hydrocarbon group, linear or branched, saturated or unsaturated, preferably saturated, comprising from 4 to 22 carbon atoms, optionally substituted by an -NH2 group, the group T being substituted by one or more hydroxyl (-OH) groups and / or interrupted by one or more groups selected from -C(O)-, -NRa- or their combinations such as -NRa-C(O)- or -C(O)-NRa-, with Ra representing a hydrogen atom or a (Ci-C4)alkyl group.

[0158] According to a first variant, T represents a divalent, linear or branched, saturated hydrocarbon group comprising from 4 to 22 carbon atoms, preferably from 10 to 22 carbon atoms, more preferably from 15 to 20 carbon atoms, optionally substituted by an -NH2 group, the group T being interrupted by one or more groups selected from -C(O)-, -NRa- or their combinations such as -NRa-(CO)- or -(CO)-NRa-, Ra being as defined previously for formula (II), preferably interrupted by one or more groups selected from -NRa-C(O)- or -C(O)-NRa-, Ra being as defined previously for formula (II) and the group T being optionally substituted by one or more hydroxyl groups (-OH).

[0159] Preferably, according to this first variant, T represents a divalent, linear or branched, saturated hydrocarbon group comprising from 10 to 22 carbon atoms, preferably from 15 to 20 carbon atoms, optionally substituted by an -NH2 group, the T group being interrupted by 2 or 3 groups selected from -NH-(CO)- or -(CO)-NH- and the T group being optionally substituted by one or more hydroxyl groups (-OH), in particular a hydroxyl group (-OH).

[0160] According to this first variant, the polyamine compound(s) B are preferably chosen from the following compounds (la) and (2a), their optical isomers, their salts, their solvates such as hydrates, and their mixtures: 9 x (the)

[0161] According to a second variant, T represents a divalent, linear or branched, saturated hydrocarbon group comprising from 4 to 22 carbon atoms, preferably from 4 to 15 carbon atoms, more preferably from 4 to 10 carbon atoms, substituted by one or more hydroxyl groups (-OH).

[0162] According to this second variant, T is preferably uninterrupted by one or more groups chosen from -C(O)-, -NRa- or their combinations such as -NRa -C(O)- or -C(O)-NRa-, Ra being as defined previously.

[0163] Preferably, according to this second variant, T represents a branched, saturated divalent hydrocarbon group comprising from 4 to 15 carbon atoms, preferably from 4 to 10 carbon atoms, substituted by one or more hydroxyl groups (-OH), preferably by a hydroxyl group (-OH).

[0164] According to this second variant, the polyamine compound(s) B are preferably chosen from the following compound (3a), its optical isomers, its salts, its solvates such as hydrates, and mixtures thereof:

[0165] The compound of formula (3) is marketed by BLD Pharmatech Ltd. (CAS: 25441-01-4).

[0166] Preferably, the polyamine compound(s) B are chosen from the following compounds (la), (2a) and (3a), their optical isomers, their salts, their solvates such as hydrates, and their mixtures: (2a) (3a).

[0167] The process according to the invention can further implement on the keratin fibers one or more (poly)amine compounds B' different from the polyamine compounds B as defined above.

[0168] The (poly)amine compound(s) B' may in particular be chosen from among polyamine compounds having several primary and / or secondary amine groups or from among amino alkoxysilanes, and more particularly from among amino alkoxysilane compounds, diamine compounds, triamine compounds, polyamino acids and their mixtures.

[0169] The (poly)amine compound(s) B' may be selected from compounds comprising from 2 to 20 carbon atoms, including non-polymer compounds; they 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 or groups 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, representing a (CrC4)alkyl group such as methyl, and R' representing a hydrogen atom or a (C1-C4)alkyl group, preferably a hydrogen atom.

[0170] By "non-polymer compound" is meant a compound that is not directly obtained by a polymerization reaction of monomers.

[0171] Examples of (poly)amine B' compounds include N-methyl-1,3-diaminopropane, N-propyl 1,3-diaminopropane, N-isopropyl 1,3-diaminopropane, N-cyclohexyl 1,3-diaminopropane, 2-(3-aminopropylamino)ethanol, 3-(2-aminoethyl)aminopropylamine, bis(3-aminopropyl)amine, 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, cystamine, xylenediamine, tris(2-aminoethyl)amine, 1,3-bis(aminomethyl)cyclohexane, 1,4-bis(aminomethyl)cyclohexane, diaminopropanol, 4,7,10-Trioxa-l,13-tridecanediamine, spermidine and C36-alkylenediamines (respectively Priamine™ 1071, 1073, 1074, 1075 marketed by CRODA).

[0172] According to a particular embodiment of the invention, the (poly)amine compound(s) B' are monoamine, namely they contain a single primary and / or secondary amine group, preferably primary (NH2).

[0173] The (poly)amine compound(s) B' may be selected from among the amino alkoxysilanes, in particular those of formula R'iSi(OR'2)z(R'3)x, in which: - R'i is a Ci-C6 hydrocarbon chain, linear or branched, saturated or unsaturated, cyclic or acyclic, substituted by a group chosen from the primary amine group NH2 or the secondary amine group -N(H)R, with R representing a Ci-C4 alkyl, an aryl, or a benzyl substituted by an amino group or by a Ci-C4 aminoalkyl group; R'i may be interrupted in its chain by a heteroatom (O, S, NH) or a carbonyl group C(O), R'i being linked to the silicon atom directly via a carbon atom, - R'2 and R'3, whether identical or different, represent a (Ci-C6)alkyl group, linear or branched. - z denotes an integer from 1 to 3, and - x denotes an integer from 0 to 2, with z + x = 3.

[0174] In particular, R'i is an acyclic chain. Preferably, R'i 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'i is a linear saturated C1-C6 hydrocarbon chain substituted with an amine group NH2. Even more preferably, R'i is a linear saturated C2-C4 hydrocarbon chain substituted with an amine group NH2.

[0175] 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.

[0176] 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.

[0177] In particular, the (poly)amine compound(s) B' are selected from amino alkoxysilanes having only one primary and / or secondary amine group, preferably primary (NH2), such as 3-aminopropyltriethoxysilane (APTES), 3-aminoethyltriethoxysilane (AETES), 3-aminopropylmethyldiethoxysilane, N-(2-aminoethyl)-3-aminopropyltriethoxysilane, 3-(m-aminophenoxy)propyltrimethoxy-silane, p-aminophenyltrimethoxysilane, and N-(2-aminoethylaminomethyl)-phenethyltrimethoxysilane.

[0178] Preferably, the (poly)amine compound(s) B' are chosen from 3-aminopropyltriethoxysilane (APTES), 3-aminoethyltriethoxysilane (AETES), 3-aminopropylmethyldiethoxysilane, and N-(2-aminoethyl)-3-aminopropyltrieth oxysilane, and more preferably 3-aminopropyltriethoxysilane (APTES), in particular that marketed by Sigma Aldrich.

[0179] The (poly)amine compound(s) B' may also be selected from amine polymers, in particular having a weight average molecular weight ranging from 500 g.mol1 to 1000000 g.mol1, preferably ranging from 500 g.mol' to 500000 g.mol1, and preferably ranging from 500 g.mol1 to 100000 g.mol1.

[0180] According to a particular embodiment of the invention, the (poly)amine compound(s) B' are monoamines and selected from polydialkylsiloxanes, in particular those 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) formula (IV) wherein: - ALK represents a (Ci-C4)alkylene group, linear or branched, preferably linear, such as propylene, - R'2 and R'3, whether identical or different, preferably identical, represent a (CrC4)alkyl group such as methyl, and - R'4 represents a (Ci-C6)alkyl group, linear or branched, preferably at C4, such as n-butyl, ne represents an integer greater than or equal to 2, preferably the value of n is such that the average molecular weight by weight of the polydimethylsiloxane ranges from 500 to 3000 g.mol1. As an example of polydimethylsiloxanes (IV), we can cite those sold under the names "MCR-A11" and "MCR-A12" by the company Gelest.

[0181] According to a particular embodiment of the invention, the (poly)amine compound(s) B' are diaminized, namely they contain two primary and / or secondary amine groups, preferably primary (NH2).

[0182] More specifically, they are chosen from compounds of formula (V) or (VI): ■ ALK[(O-ALK')m-NH2]2 (V) or ■ H2N-ALK-Si(R')2-[O-Si(R')2]mO-Si(R)2-ALK'-NH2 (VI) formulas (V) and (VI) in which: - ALK and ALK', whether identical or different, represent a (Ci-C6)alkylene group, linear or branched, preferably linear, such as propylene, - R', identical or different, represents an (Ci-C4)alkyl group, such as methyl, - m represents an integer greater than or equal to 0, preferably the value of m is such that the average molecular weight by weight of the compound (V) or (VI) goes from 500 g.mol1 to 55000 g.mol1.

[0183] 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.

[0184] The (poly)amine compound(s) B' which are diaminized are particularly the 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 the compounds known under the reference Jeffamine of the Huntsman company, and more particularly 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.

[0185] According to a particular embodiment of the invention, the (poly)amine compound(s) B' are triamine, namely they contain three primary and / or secondary amine groups, preferably primary (NH2). More particularly, they are selected from triamine polyethers, notably of formula ALK'”[(O-ALK')m-NH2]3, with ALK' as defined above and ALK”' representing a trivalent (Ci-C6)alkylene group, linear or branched, and m representing an integer greater than or equal to 0.

[0186] As B' (poly)amine compounds which are triamined, triamine polyethers, such as those sold under the name Jeffamine T-403, are particularly cited.

[0187] According to another particular embodiment of the invention, the (poly)amine compound(s) B' comprises more than three primary and / or secondary amine groups, preferably primary (NH2).

[0188] In this variant, the (poly)amine compound(s) B' are in particular chosen from poly(meth)acrylates or poly(meth)acrylamides bearing amine functions primary or secondary lateral, such as poly(3-aminopropyl)methacrylamide and poly(2-aminoethyl) methacrylate.

[0189] Preferably, the (poly)amine B' compounds are chosen from chitosans (in particular poly(D-glucosamine)), and polydimethylsiloxanes comprising primary amine groups at the end of the chain and / or on side chains.

[0190] According to this variant, the (poly)amine compound(s) B' are in particular selected from 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; 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 having 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, notably acrylamidopropylamine-based; and poly(D-Glucosamine), for example, sold under the reference Kionutrime CSG® by Kytozyme.

[0191] According to a particular embodiment, polydimethylsiloxanes comprising primary amine groups at the end of the chain and / or on side chains are selected from compounds of the following formula (VII): Ra-Si(Rb)(Rc)-O-[Si(Rb)(Rc)-O]m-[Si(ALK1-NH2)(Ra)-O]n-Si(Rb)(Rc)-Ra(VII) formula (VII) in which: - Ra, identical or different, represents a hydroxyl 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, possibly 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 average molecular mass by weight of the compound of formula (VII) goes from 1000 g.mol1 to 500000 g.mol1.

[0192] According to a preferred embodiment, formula (VII) is such that Ra, Rb, and Rc represent a methyl group, ALK1 represents a propylene group, and n and m are such that the values n and m are such that the average molecular weight by weight of polydimethylsiloxane ranges from 1000 g.mol1 to 55000 g.mol1.

[0193] Examples of polydimethylsiloxanes of formula (VII) include those sold under the names "AMS-132", "AMS-152", "AMS-162", "AMS-163", "AMS-191" and "AMS-1203" by the company Gelest.

[0194] According to another variant, 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.

[0195] As an amino polymer, polytetrahydrofuran (or polytetramethylene glycol) α, co-diamine, and polybutadienes α, co-diamine may also be cited.

[0196] According to a particular embodiment of the invention, the (poly)amine compounds B' are 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.

[0197] Preferably, the (poly)amine compound(s) B' are chosen from: a) (poly)amine compounds having more than three primary and / or secondary amine groups, preferably primary (NH2), in particular chitosans such as poly(D-Glucosamine) and polylysine, b) diamine polyethers, in particular polyethylene glycol α, co-diamine, with an amine function at the end of the chain, c) triamine polyethers, such as Jeffamine T-403, d) aminoalkoxysilanes, in particular APTES, e) NH2-alk-NH2 polyamine compounds, in which alk denotes a C2-C20 hydrocarbon divalent chain, optionally substituted by a hydroxyl group (-OH) and / or optionally interrupted by one or more heteroatoms chosen from -O-, -N(R)- with R denoting a hydrogen atom or a C1-C4 alkyl radical, notably spermidine, 4,7,10-Trioxa-l,13-tridecanediamine and 1,3-diamino-2-propan-1-ol,(f) polydialkylsiloxanes comprising primary amine groups at the end of the chain or on side chains, in particular polydimethylsiloxanes comprising primary amine groups, more particularly poly(dimethoxysiloxane) terminated by bis(3-aminopropyl) (PDMS-diNH2) and amodimethicones comprising amine groups on side chains, even more particularly bis-cetearyl amodimethicone, (g) and mixtures thereof.

[0198] Preferably, the (poly)amine compound(s) B' are chosen from a), and their mixtures, preferably polylysine. Additional characteristics of the process

[0199] The process according to the invention can be implemented on natural keratin fibers, in particular natural hair.

[0200] The process according to the invention can also be implemented on damaged and / or sensitized keratin fibers, in particular damaged and / or sensitized hair.

[0201] By "damaged keratin fibers" is meant dry, rough, brittle, split and / or soft keratin fibers.

[0202] By "sensitized keratin fibres" is meant bleached, artificially coloured, straightened and / or permed keratin fibres.

[0203] The process according to the invention can advantageously be implemented on curly, frizzy or kinky keratin fibers, in particular curly, frizzy or kinky hair.

[0204] According to a first variant, the process comprises applying to the keratin fibers a composition (A) comprising the compound(s) A and optionally one or more coloring agents selected from pigments, direct dyes, and mixtures thereof, preferably from pigments, and then a composition (B) distinct from composition (A) comprising the polyamine compound(s) B and optionally one or more coloring agents selected from pigments, direct dyes, and mixtures thereof, preferably from pigments.

[0205] According to this first variant, composition (A) preferably does not include polyamine compound(s) B and composition (B) preferably does not include compound(s) A.

[0206] According to a second variant, the process includes applying to the keratin fibers a composition (C) comprising the compound(s) A, the polyamine compound(s) B and optionally one or more coloring agents selected from pigments, direct dyes, and mixtures thereof, preferably from pigments.

[0207] According to this second variant, composition (C) can be obtained by extemporaneous mixing of a first composition comprising the compound(s) A and optionally one or more coloring agents selected from pigments, direct dyes, and their mixtures, preferably from pigments with a second composition comprising the polyamine compound(s) B and optionally one or more coloring agents selected from pigments, direct dyes, and their mixtures, preferably from pigments.

[0208] Preferably, the process according to the present invention is a process for permanently shaping keratin fibers, preferably a process for relaxing loops and / or smoothing keratin fibers.

[0209] When the process according to the present invention is a process for permanently shaping keratin fibers, it advantageously does not use coloring agent(s) on the keratin fibers.

[0210] The applicant has found, surprisingly, that the process according to the present invention allows for the durable shaping of keratin fibers, including a substantial reduction in hair volume and, when the hair is curly, better relaxation of the curls and / or better definition of them, the effect obtained exhibiting good resistance to water and to one or more shampoos, in order to guarantee that the shaping lasts over time.

[0211] Preferably, the process according to the present invention is a process for coloring keratin fibers using on the keratin fibers one or more coloring agents chosen from pigments, direct dyes, and their mixtures, preferably from pigments.

[0212] The applicant also found, surprisingly, that when the process according to the invention is a process for coloring keratin fibers, it makes it possible to obtain intense, chromatic colors with good color rise, as well as good resistance to water and to one or more shampoos, in order to guarantee color retention over time, particularly in terms of intensity and / or chromaticity.

[0213] According to a third variant, the process according to the present invention is a process for coloring keratin fibers comprising applying to the keratin fibers a composition (A) comprising compound(s) A and then a composition (B) distinct from composition (A) comprising polyamine compound(s) B, it being understood that at least one of the compositions (A) or (B), preferably composition (A) comprises one or more coloring agents selected from pigments, direct dyes, and mixtures thereof, preferably from pigments.

[0214] According to this third variant, when composition (A) comprises one or more coloring agents selected from pigments, direct dyes, and their mixtures, composition (A) can be obtained by extemporaneous mixing of a first composition comprising the compound(s) A with a second composition comprising the coloring agent(s) and / or when composition (B) comprises one or more coloring agents selected from pigments, direct dyes, and their mixtures, composition (B) can be obtained by extemporaneous mixing of a first composition comprising the polyamine compound(s) B with a second composition comprising the coloring agent(s).

[0215] According to this third variant, composition (A) preferably does not include polyamine compound(s) B and composition (B) preferably does not include compound(s) A.

[0216] According to a fourth variant, the process according to the present invention is a process for coloring keratin fibers comprising the application on the keratin fibers of a composition (C) comprising the compound(s) A, the polyamine compound(s) B and the coloring agent(s) selected from pigments, direct dyes, and mixtures thereof, preferably from pigments.

[0217] According to this fourth variant, composition (C) can be obtained by extemporaneous mixing of a first composition comprising compound(s) A with a second composition comprising polyamine compound(s) B, it being understood that the first and / or second composition includes the coloring agent(s).

[0218] According to this fourth variant, composition (C) can alternatively be obtained by extemporaneous mixing of a first composition comprising compound(s) A with a second composition comprising polyamine compound(s) B and a third composition comprising the coloring agent(s). Coloring agents

[0219] When the process according to the present invention is a process for coloring keratin fibers, it uses on the keratin fibers one or more coloring agents chosen from pigments, direct dyes, and their mixtures, preferably from pigments. The pigments

[0220] By "pigment" is meant 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% by weight (i.e. gram of pigment per liter of water).

[0221] The pigments that can be used are in particular chosen from among the organic and / or mineral pigments known in the art, in particular those described in Kirk-Othmer's Encyclopedia of Chemical Technology and in Ullmann's Encyclopedia of Industrial Chemistry.

[0222] They may be natural, of natural origin, or not.

[0223] These pigments may be in the form of powder or pigment paste. They may be coated or uncoated.

[0224] 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.

[0225] The pigment may be a mineral pigment. By mineral pigment is meant any pigment that meets the definition in the Ullmann Encyclopedia in the chapter on inorganic pigments. Examples of mineral pigments useful in the present invention include iron or chromium oxides, manganese violet, ultramarine blue, chromium hydrate, ferric blue, titanium dioxide, and stannic oxide (tin oxide).

[0226] 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.

[0227] 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.

[0228] 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.

[0229] As an example, we can also cite pigment pastes of organic pigment such as the products sold by the company HOECHST under the name: - COSMENYL YELLOW IOG: Pigment YELLOW 3 (Cl 11710); - COSMENYL YELLOW G: Pigment YELLOW 1 (Cl 11680); - ORANGE COSMENYL GR: Pigment ORANGE 43 (Cl 71105); - COSMENYL RED R: Pigment RED 4 (Cl 12085); - CARMIN COSMENYL FB: Pigment RED 5 (Cl 12490); - VIOLET COSMENYL RL: Pigment VIOLET 23 (Cl 51319); - COSMENYL BLUE A2R: Pigment BLUE 15.1 (Cl 74160); - VERT COSMENYL GG: Pigment GREEN 7 (Cl 74260); - COSMENYL BLACK R: Pigment BLACK 7 (Cl 77266).

[0230] 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.

[0231] 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.

[0232] The inorganic substrates on which the dyes are adsorbed are, for example, alumina, silica, calcium sodium borosilicate or calcium aluminium borosilicate, and aluminium.

[0233] 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).

[0234] As examples of lacquers, we can cite the product known under the following name: D & C Red 7 (CI 15 850 :1).

[0235] 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.

[0236] 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.

[0237] 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), and Prestige Bronze. marketed by Eckart (Mica-Fe2O3), Syncrystal marketed by Eckart (Mica-TiO2-SnO2), Colorona marketed by Merck (Mica-TiO2-Fe2O3).

[0238] We can also mention gold-colored mother-of-pearl, notably marketed by BASF under the names Brilliant Gold 212G (Timica), Gold 222C (Cloisonne), Sparkle Gold (Timica), Gold 4504 (Chromalite) and Monarch Gold 233X (Cloisonne); bronze mother-of-pearl, notably marketed by MERCK under the names Bronze Fine (17384) (Colorona) and Bronze (17353) (Colorona) and by BASF under the name Super Bronze (Cloisonne); orange mother-of-pearl, notably marketed by BASF under the names Orange 363C (Cloisonne) and Orange MCR 101 (Cosmica) and by MERCK under the names Passion Orange (Colorona) and Matte Orange (17449) (Microna); brown-tinted mother-of-pearl, notably marketed by BASF under the names Nu-antique copper 340XB (Cloisonne) and Brown CL4509 (Chromalite); copper-tinted mother-of-pearl, notably marketed by BASF under the name Copper 340A (Timica);red-tinted mother-of-pearl, notably marketed by MERCK under the name Sienna fine (17386) (Colorona); yellow-tinted mother-of-pearl, notably marketed by BASF under the name Yellow (4502) (Chromalite); red-tinted mother-of-pearl with a gold sheen, notably marketed by BASF under the name Sunstone G012 (Gemtone); pink mother-of-pearl, notably marketed by BASF under the name Tan opale G005 (Gemtone);black mother-of-pearl with a gold sheen, notably marketed by BASF under the name Nu antique bronze 240 AB (Timica); blue mother-of-pearl, notably marketed by MERCK under the name Matte blue (17433) (Microna); white mother-of-pearl with a silver sheen, notably marketed by MERCK under the name Xirona Silver; and orange-pink-green-gold mother-of-pearl, notably marketed by MERCK under the name Indian summer (Xirona), and their mixtures.

[0239] As further examples of nacres, we can also mention particles comprising a borosilicate substrate coated with titanium oxide.

[0240] Particles with a glass substrate coated with titanium oxide are notably sold under the name METASHINE MC1080RY by the company TOYAL.

[0241] 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.

[0242] 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) that constitute them and their physical and chemical nature, and surface condition, enable them to reflect incident light. This reflection may, where appropriate, have sufficient intensity to create, on the surface of the composition or mixture, when applied to the makeup support, highlights visible to the naked eye, that is to say, brighter points that contrast with their surroundings by appearing to shine.

[0243] 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.

[0244] These particles can have various shapes, including being platelet-shaped or globular, particularly spherical.

[0245] 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.

[0246] 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.

[0247] 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.

[0248] 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.

[0249] The reflective material may include a layer of metal or a metallic material.

[0250] Reflective particles are described in particular in documents JP-A-09188830, JP-A-10158450, JP-A-10158541, JP-A-07258460 and JP-A-05017710.

[0251] 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.

[0252] 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.

[0253] Particles comprising a metallic substrate such as silver, aluminium, iron, chromium, nickel, molybdenum, gold, copper, zinc, tin, magnesium, steel, bronze, titanium may also be used, said substrate being coated with at least one layer of at least one metallic oxide such as titanium oxide, aluminium oxide, iron oxide, cerium oxide, chromium oxide, silicon oxides and mixtures thereof.

[0254] An example can be cited as aluminium, bronze or copper powders coated with SiO2 marketed under the name VISIONAIRE by the company ECKART.

[0255] 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.

[0256] 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.

[0257] The size of the pigment used according to the present invention is generally between 5 nm and 200 pm, preferably between 7 nm and 80 pm, and more preferably between 10 nm and 50 pm.

[0258] Pigments can be dispersed in a composition by means of a dispersing agent.

[0259] 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 bind 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 1,2-hydroxystearic acid, and of C8 to C2O fatty acids and polyols such as glycerol and diglycerin, are used. such as poly(12-hydroxystearic acid) stearate with a molecular weight of approximately 750 g / mol, such as that sold under the name Solsperse 21 000 by Avecia, polygyceryl-2 dipolyhydroxystearate (CTFA) sold under the reference Dehymyls PGPH by Henkel, or polyhydroxystearic acid such as that sold under the reference Arlacel P100 by Uniqema, and mixtures thereof.

[0260] Other dispersants that can be used in the compositions of the invention include quaternary ammonium derivatives of polycondensed fatty acids such as Solsperse 17 000 sold by Avecia, and polydimethylsiloxane / oxypropylene mixtures such as those sold by Dow Corning under the references DC2-5185 and DC2-5225 C.

[0261] The pigments used can be surface treated with an organic agent.

[0262] 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 can 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.

[0263] The useful surface-treated pigments may also have been treated with a mixture of these compounds and / or have undergone several surface treatments.

[0264] The surface-treated pigments useful in the context of the present invention can be prepared according to surface treatment techniques well known to those skilled in the art or found as such in the commercial market.

[0265] Preferably, the surface-treated pigments are covered by an organic layer.

[0266] 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.

[0267] 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.

[0268] Preferably, an organic agent covalently linked to the pigments will be used.

[0269] 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.

[0270] Preferably, the surface treatments of the pigments are chosen from the following treatments: - a PEG-Silicone treatment such as the AQ surface treatment marketed by LCW; - a Methicone treatment such as the SI surface treatment marketed by LCW; - a Dimethicone treatment such as the Covasil 3.05 surface treatment marketed by LCW; - a Dimethicone / Trimethylsiloxysilicate treatment such as the Covasil 4.05 surface treatment marketed by LCW; - a Magnesium Myristate treatment such as the MM surface treatment marketed by LCW; - a Dimyristate Aluminium treatment such as the MI surface treatment marketed by Miyoshi; - a Perfluoropolymethylisopropyl ether treatment such as the FHC surface treatment marketed by LCW; - an Isostearyl Sebacate treatment such as the HS surface treatment marketed by Miyoshi; - a Perfluoroalkyl Phosphate treatment such as the PF surface treatment marketed by Daito; - an acrylate / dimethicone copolymer and perfluoalkyl phosphate treatment such as the FSA surface treatment marketed by Daito; - a Polymethylhydrogen siloxane / Perfluoroalkyl Phosphate treatment such as the FS01 surface treatment marketed by Daito; - an Acrylate / Dimethicone Copolymer treatment such as the ASC surface treatment marketed by Daito; - an Isopropyl Titanium Triisostearate treatment such as the ITT surface treatment marketed by Daito; - an Acrylate copolymer treatment such as the APD surface treatment marketed by Daito; - a Perfluoroalkyl Phosphate / Isopropyl Titanium Triisostearate treatment such as the PF + ITT surface treatment marketed by Daito.

[0271] According to a particular embodiment of the invention, the dispersing agent is present with organic or inorganic pigments in submicron-sized particulate form in the coloring composition.

[0272] 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.

[0273] According to one embodiment, the dispersing agent and the pigment(s) are present in an amount (dispersant: pigment) 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.

[0274] The dispersing agent(s) may therefore have a silicone skeleton, such as silicone polyether and amino-silicone dispersants. Suitable dispersing agents include: - amino-silicones, i.e. silicones comprising one or more amino groups, such as 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 les polymers, - silicone acrylates such as Tego® RC 902, Tego® RC 922, Tego® RC 1041, and Tego® RC 1043, marketed by Evonik, - 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.

[0275] According to a particular embodiment, the dispersing agent(s) are of the amino-silicone type and are cationic.

[0276] Preferably, the pigment(s) is / are chosen from mineral pigments, mixed mineral-organic pigments, organic pigments or special effect pigments.

[0277] In one variant of the invention, the pigment(s) according to the invention are organic pigments, preferably organic pigments treated on the surface by an organic agent chosen from silicone compounds.

[0278] In another embodiment of the invention, the pigment or pigments according to the invention are mineral pigments.

[0279] In another embodiment of the invention, the pigments according to the invention are special effect pigments, preferably pearlescent pigments, more preferably colored pearlescent pigments.

[0280] Preferably, the pigment(s) used in the process of the invention are chosen from among mother-of-pearl, carbon blacks such as Black 2, iron oxides in particular red, brown or black and micas coated with iron oxide, triarylmethane pigments in particular blue and violet such as BLUE 1 LAKE, azo pigments in particular red such as D&C RED 7, alkali or alkaline-earth metal salts of lithol red such as the calcium salt of lithol red B, and mixtures thereof. Direct dyes

[0281] The term "direct dye" means a natural and / or synthetic dye, including in the form of extract(s), distinct from oxidation dyes. These are colored compounds that diffuse superficially onto the fiber. They can be ionic or non-ionic, i.e., anionic, cationic, neutral, or non-ionic.

[0282] Synthetic direct dyes are for example chosen from those classically used in direct dyeing, and among which we can mention all the aromatic and / or non-aromatic dyes in common use such as benzene, azo, hydrazono, (hetero)aryl, tri(hetero)arylmethane, (poly)methine, carbonyl, azinic, porphyrinic, metalloporphyrinic, xanthenic, quinonic, and in particular anthraquinone, indoamine, phthalocyanine and their mixtures.

[0283] Among the benzene nitro direct dyes, the following may be mentioned: 1,4-diamino-2-nitrobenzene; 1-amino-2-nitro-4-[3-hydroxyethylaminobenzene; 1-amino-2-nitro-4-bis([3-hydroxyethyl)-aminobenzene; 1,4-bis([3-hydroxyethylamino)-2-nitrobenzene; 1-[3-hydroxyethylamino-2-nitro-4-bis-([3-hydroxyethylamino)-benzene; 1-[3-hydroxyethylamino-2-nitro-4-aminobenzene; 1-[3-hydroxyethylamino-2-nitro-4-(ethyl)([3-hydroxyethyl)-aminobenzene; 1-amino-3-methyl-4-[3-hydroxyethylamino-6-nitrobenzene; 1-amino-2-nitro-4-[3-hydroxyethylamino-5-chlorobenzene; 1,2-diamino-4-nitrobenzene; l-amino-2-[3-hydroxyethylamino-5-nitrobenzene; 1,2-bis-([3-hydroxyethylamino)-4-nitrobenzene; l-amino-2-tris-(hydroxymethyl)-methylamino-5-nitrobenzene; l-Hydroxy-2-amino-5-nitrobenzene; l-Hydroxy-2-amino-4-nitrobenzene; l-Hydroxy-3-nitro-4-aminobenzene; l-Hydroxy-2-amino-4,6-dinitrobenzene; l-[3-hydroxyethyloxy-2-[3-hydroxyethylamino-5-nitrobenzene; l-Methoxy-2-[3-hydroxyethylamino-5-nitrobenzene;l-[3-hydroxyethyloxy-3-methylamino-4-nitrobenzene; 1-[3,Y-dihydroxypropyloxy-3-methylamino-4-nitrobenzene; l-[3-hydroxyethylamino-4-[3,Y-dihydroxypropyloxy-2-nitrobenzene; 1-[3,Y-dihydroxypropylamino-4-trifluoromethyl-2-nitrobenzene; l-[3-hydroxyethylamino; -4-trifluoromethyl-2-nitrobenzene; l-[3-hydroxyethylamino-3-methyl-2-nitrobenzene; lP-aminoethylamino-5-methoxy-2-nitrobenzene; l-Hydroxy-2-chloro-6-ethylamino-4-nitrobenzene; l-Hydroxy-2-chloro-6-amino-4-nitrobenzene; l-Hydroxy-6-bis-([3-hydroxyethyl)-amino-3-nitrobenzene; lP-hydroxyethylamino-2-nitrobenzene; 1-Hydroxy-4-[3-hydroxyethylamino-3-nitrobenzene.

[0284] Among the azo direct dyes, we can cite: Basic Red 51, Basic Orange 31, Disperse Red 17, Acid Yellow 9, Acid Black 1, Basic Red 22, Basic Red 76, Basic Yellow 57, Acid Yellow 36, Acid Orange 7, Acid Red 33, Acid Red 35, Acid Yellow 23, Acid Orange 24, Disperse Black 9, Basic Brown 16, Basic Brown 17.

[0285] Among the direct hydrazono colorants, we can mention: Basic Yellow 87.

[0286] Among the aryl nitrate direct dyes, the following may be mentioned: HC Blue 2, HC Yellow 2, HC Red 3, 4-hydroxypropylamino-3-nitrophenol, A,A'-bis-(2-hydroxyethyl)-2-nitro-pheny lenediamine.

[0287] Among the triarylmethane direct dyes, we can cite: Basic Violet 1, Basic Violet 2, Basic Violet 3, Basic Violet 4, Basic Violet 14, Basic Blue 1, Basic Blue 7, Basic Blue 26, Basic green 1, Basic Blue 77 (also called HC Blue 15), Acid Blue 1; Acid Blue 3; Acid Blue 7, Acid Blue 9; Acid Violet 49; Acid green 3; Acid green 5; Acid Green 50; tetrabromophenol blue.

[0288] Xanthenic dyes include: Acid Red 92; Acid Red 52

[0289] Among the quinone direct dyes, the following may be mentioned: Disperse Red 15, Solvent Violet 13, Acid Violet 43, Disperse Violet 1, Disperse Violet 4, Disperse Blue 1, Disperse Violet 8, Disperse Blue 3, Disperse Red 11, Acid Blue 62, Disperse Blue 7, Basic Blue 22, Disperse Violet 15, Basic Blue 99, as well as the following compounds: 1-N-methylmorpholiniumpropylamino-4-hydroxyanthraquinone, 1-aminopropylamino-4-methylaminoanthraquinone, 1-aminopropylamino-anthraquinone, 5-[3-hydroxyethyl-1,4-diaminoanthraquinone, 2-aminoethylamino-anthraquinone, 1,4-bis-([3,γ-dihydroxypropylamino)-anthraquinone, Acid Blue 25, Acid Blue 43, Acid Blue 78, Acid Blue 129, Acid Blue 138, Acid Blue 140, Acid Blue 251, Acid Green 25, Acid Green 41, Acid Violet 42, Mordant Red 3, Acid Black 48, HC Blue 16.

[0290] Among the direct azinic dyes, we can mention: Basic Blue 17, Basic Red 2.

[0291] Among the indoamine direct dyes, we can mention: 2-[3-hydroxyethylamino- 5-[bis-([3-4'-hydroxyethyl)amino]anilino-l,4-benzoquinone, 2-[3-hydroxyethylamino-5-(2'-methoxy-4'-amino)anilino-l,4-benzoquinone, 3-N(2'-chloro-4'-hydroxy)phenyl-acetylamino-6-methoxy-l,4-benzoquinone imine, 3-N(3'-chloro-4'-methylamino)phenyl-ureido-6-methyl-1,4-benzoquinone imine, 3-[4'-N-(ethyl,carbamylmethyl)-amino]-phenyl-ureido-6-methyl-1,4-benzoquinone imine.

[0292] Natural direct colorants are for example chosen from lawsone, juglone, indigo, leuco indigo, indirubine, isatin, hennotannic acid, alizarin, carthamine, morine, purpurine, carminic acid, kermesic acid, laccaic acid, purpurogallin, protocatechaldehyde, curcumin, spinulosin, apigenidine, orceins, carotenoids, betanin, chlorophylls, chlorophyllins, monascus, polyphenols or orthodiphenols.

[0293] Among the useful orthodiphenols according to the invention, the following may be mentioned: catechin, quercetin, brazilin, hematein, hematoxylin, chlorogenic acid, caffeic acid, gallic acid, L-DOPA, cyanidin, (-)-Epicatechin, (-)-Epigallocatechin, (-)-Epigallocatechin 3-gallate (EGCG), isoquercetin, pomiferin, esculetin, 6,7-Dihydroxy-3-(3-hydroxy-2,4-dimethoxyphenyl)coumarin, Santalin A and B, mangiferin, butein, maritimetin, sulfuretin, robtein, betadin, pericampylinone A, theaflavin, proanthocyanidin A2, proanthocyanidin B2, proanthocyanidin Cl, procyanidins DP 4-8, tannic acid, purpurogallin, 5,6-Dihydroxy-2-methyl-1,4-naphthoquinone, Alizarin, Wedelolactone and natural extracts containing them.

[0294] Advantageously, the colouring agent(s) are present in composition (A) or (B) or (C) in a total content of 0.001% to 20% by weight, preferably 0.01% to 15% by weight, more preferably 0.1% to 15% by weight, and better 0.5% to 15% by weight relative to the total weight of the composition comprising them.

[0295] According to a preferred embodiment, the coloring agent(s) are chosen from pigments.

[0296] The pigment(s) may be present in composition (A) or (B) or (C) in a total content of 0.001% to 20% by weight, preferably 0.01% to 15% by weight, more preferably 0.1% to 15% by weight, and better 0.5% to 10% by weight, relative to the total weight of the composition comprising them.

[0297] Compositions (A), (B) and / or (C) can be applied to dry or wet keratin fibers, preferably with a weight ratio of the amount of composition applied relative to the amount of hair ranging from 0.1 to 10, preferably ranging from 0.3 to 5.

[0298] Preferably, the application of compositions (A), (B) and / or (C) to keratin fibers is carried out at room temperature, i.e. at a temperature between 25 °C and 30 °C.

[0299] Keratin fibers are preferably dried after application of compositions (A), (B) and / or (C).

[0300] When dried, keratin fibers can be air-dried or dried with a drying device such as a helmet, a hair dryer or a climazon.

[0301] Preferably, compound(s) A are present in composition (A) or (C) in a total content ranging from 0.2% to 80% by weight, preferably ranging from 0.5% at 50% by weight, more preferably ranging from 2% to 35% by weight, relative to the total weight of the composition comprising it or them.

[0302] Preferably, the polyamine compound(s) B are present in composition (B) or (C) in a total content ranging from 0.2% to 60% by weight, preferably ranging from 0.5% to 40% by weight, more preferably ranging from 1% to 35% by weight, relative to the total weight of the composition comprising them.

[0303] Compositions (A), (B) and (C) are cosmetic compositions, i.e. which comprise a cosmetically acceptable medium, i.e. a medium compatible with human keratin fibers.

[0304] According to a preferred embodiment, compositions (A), (B) and / or (C) comprise water and / or one or more solvents S selected from polar and / or protic solvents, oils distinct from compounds A, and mixtures thereof.

[0305] Polar and / or protic solvents are preferably chosen from monoalcohols having 2 to 6 carbon atoms such as ethanol, propanol, n-butanol, isopropanol, isobutanol, tert-butanol, pentanol, hexanol, and mixtures thereof, in particular n-butanol, ethanol, and mixtures thereof, esters having 3 to 8 carbon atoms such as ethyl lactate, more preferably chosen from ethanol, ethyl lactate, and mixtures thereof.

[0306] The distinct oils of compounds A are preferably chosen from hydrocarbon oils, more preferably chosen from C8-Ci6 hydrocarbon oils, even more preferably chosen from iso-alkanes, and better chosen from Ci3-Ci6 iso-paraffins, isododecane, isohexadecane, and mixtures thereof, and even better isododecane.

[0307] By "oil" is meant a non-aqueous compound, immiscible with water, liquid at room temperature (20 °C) and atmospheric pressure (760 mm Hg).

[0308] By "hydrocarbon oil" is meant an oil formed essentially, or even composed, of carbon and hydrogen atoms, and possibly of oxygen and nitrogen atoms, and not containing silicon or fluorine atoms. It may contain alcohol, ester, ether, carboxylic acid, amine and / or amide groups.

[0309] When compositions (A), (B) and / or (C) include water, the water is present in a total weight content ranging from 1% to 99% by weight, preferably ranging from 20% to 80% by weight, relative to the total weight of the composition comprising it.

[0310] When compositions (A), (B) and / or (C) comprise one or more solvents S, the solvent(s) S are present in a total weight content ranging from 0.01% to 99% by weight, preferably ranging from 0.01% to 80% by weight, relative to the total weight of the composition comprising it.

[0311] Compositions (A), (B) and (C) can be presented in all galenic forms classically used for hair application. Composition (C)

[0312] According to a second aspect, the present invention relates to a composition (C) comprising the compound(s) A as defined above, the polyamine compound(s) B as defined above and optionally one or more coloring agents selected from pigments, direct dyes, and mixtures thereof, preferably from pigments. Kit

[0313] According to a third aspect, the present invention relates to a two- or three-compartment device comprising: - a first compartment containing a composition (A) comprising the compound(s) (A) as defined above and possibly one or more coloring agents chosen from pigments, direct dyes, and their mixtures, preferably from pigments; - a second compartment separate from the first compartment containing a composition (B) comprising the polyamine compound(s) B as defined above and optionally one or more coloring agents selected from pigments, direct dyes, and mixtures thereof, preferably from pigments; and - optionally a third compartment separate from the first and second compartments containing a composition comprising one or more coloring agents selected from pigments, direct dyes, and mixtures thereof, preferably from pigments. Uses

[0314] According to a fourth aspect, the present invention relates to the use of one or more compounds A as defined above associated with one or more polyamine compounds B as defined above or of a composition (C) comprising the compound(s) A as defined above and the polyamine compound(s) B as defined above, for the relaxation of curls and / or the smoothing of keratin fibers.

[0315] According to a fifth aspect, the present invention relates to the use of one or more compounds A as defined above, combined with one or more polyamine compounds B as defined above and one or more coloring agents selected from pigments, direct dyes, and mixtures thereof, preferably from pigments, or of a composition (C) comprising the compound(s) A as defined above, the polyamine compound(s) B as defined above, and the coloring agent(s) selected from pigments, direct dyes, and mixtures thereof, for the coloring of keratin fibers. Examples

[0316] The following examples serve to illustrate the invention without, however, being limiting in nature.

[0317] In the following examples, unless otherwise indicated, where compositions are implemented, the contents are indicated as a mass percentage in relation to the total weight of the composition considered.

[0318] Examples A to I: Examples of synthesis of compounds of formula (I)

[0319] Example A: Synthesis of castor oil with acetoacetate function (Compound No. 1)

[0320] The synthesis is represented by the following preparation diagram:

[0321] In a 250 mL SVL® reactor equipped with mechanical stirring, a thermometer, and a distillation column, 50 g of castor oil (commercially available from Société Interchimie) and 25.40 g of tert-butyl acetoacetate are introduced. The reaction mixture is heated to 130 °C using an oil bath. After 7 hours, the reaction mixture is cooled, transferred to a 250 mL bulb flask, and heated to 120 °C under continuous vacuum using a rotary evaporator for 1 hour. A slightly yellow oil is obtained.

[0322] Example B: Synthesis of hydroxylated castor oil with acetoacetate function (Compound No. 2)

[0323] The synthesis is represented by the following preparation scheme: Step a)#:

[0326] In step a), the hydroxylated castor oil is prepared: In a 250 mL round-bottom flask equipped with a magnetic stirrer and under argon, 10 g of castor oil (commercially available from Interchimie), 9 g of 3-Mercapto-1,2-propanediol (commercially available from Sigma Aldrich), and 0.7 g of 2-Hydroxy-2-methylpropiophenone (commercially available from Sigma Aldrich) are added to 20 mL of ethyl acetate and stirred for 5 minutes under argon. The reaction mixture is then irradiated under a UV lamp (100 W, 365 nm) for 4 hours and subsequently washed 3 times with saturated NaCl water.

[0327] The organic phase is separated, dried over MgSO4, and then concentrated under vacuum. Finally, the solvent, traces of thiol, and photoinitiator (2-Hydroxy 2-methylpropiophenone) are removed by distillation under reduced pressure. The resulting product is used as is in the next step.

[0328] In step b), the hydroxylated castor oil is functionalized with acetoacetate groups: 10 g of hydroxylated castor oil obtained in step a) and 12 g of tert-butyl acetoacetate are introduced into a 250 mL round-bottom flask equipped with a magnetic stirrer. The reaction mixture is heated to 130 °C using an oil bath. After 4 hours, the reaction mixture is placed under continuous vacuum for 1 hour. A viscous, yellow-colored oil is obtained.

[0329] Example C: Synthesis of epoxidized oil with acetoacetate function (Compound No. 3)

[0330] The synthesis is represented by the following preparation scheme: Step a)#:

[0331] Step b)#:

[0332]

[0333] In step a), in a 500 mL S VL® reactor equipped with mechanical stirring, an argon inlet, and a distillation column, 200 g of epoxidized oil (Vikoflex 7170 marketed by Arkema), 50.4 g of lactic acid, and 6.52 g of caffeine are introduced. The reaction mixture is heated at 120 °C for 5 hours. The polyhydroxylated compound is obtained. A slightly yellow, viscous oil is produced.

[0334] In step b), in a 500 mL S VL® reactor equipped with mechanical stirring, an argon inlet, and a distillation column, 165 g of the polyhydroxylated compound obtained in step a) and 116.74 g of tert-butylacetoacetate are introduced. The reaction mixture is heated between 130 °C and 140 °C for 5 hours. After 5 hours of heating, the mixture is placed under vacuum at 50 mbar at 140 °C. A viscous, orange-colored oil is obtained.

[0335] The oil obtained is diluted with ethyl acetate and washed three times with a saturated sodium bicarbonate solution, then twice with water. The organic phase is filtered through MgSO4, and then the ethyl acetate is distilled using a rotary evaporator at 100 °C under reduced pressure. A slightly orange, viscous oil is obtained.

[0336] Example D: Synthesis of soybean oil with acetoacetate function (Compound No. 4)

[0337] The synthesis is represented by the following preparation scheme: Step a)#: 88

[0339] In step a), in a 250 mL flask equipped with a magnetic stirrer, 10 g of soybean oil (Henry Lamotte Oils), 10 g of 3-Mercapto-1,2-propanediol (marketed by Sigma Aldrich) and 0.8 g of 2-Hydroxy 2-methylpropiophenone (marketed by Sigma Aldrich) are added to 25 mL of ethyl acetate and stirred for 5 minutes under argon. The reaction mixture

[0340]

[0341]

[0342]

[0343] The sample is then irradiated under a UV lamp (100 W, 365 nm) for 4 hours, and then washed 3 times with saturated NaCl water. The organic phase is separated, dried over MgSO4, and then concentrated under vacuum. The solvent, traces of thiol, and photoinitiator are removed by distillation under reduced pressure. In step b), 10 g of hydroxylated soybean oil obtained in step a) and 14 g of tert-butyl acetoacetate are introduced into a 250 mL round-bottom flask equipped with a magnetic stirrer. The reaction mixture is then heated to 130 °C using an oil bath. After 4 hours, the reaction mixture is cooled and placed under continuous vacuum for 1 hour to remove the excess tert-butyl acetoacetate. A viscous, yellow oil is obtained. Example E: Synthesis of an "acidic" oil with acetoacetate function (Compound No. 5) The synthesis is represented by the following preparation scheme: Step a)#:

[0344] Step b)#: Step c)#:

[0345]

[0346] In step a), 100 g of citric acid and 419 g of oleic alcohol are introduced into a 500 mL S VL® reactor equipped with mechanical stirring and a distillation column. The reaction mixture is heated to 190 °C using a heating mantle. for 7 hours, then at 220 °C for 5 hours. The reaction is monitored by acid number. When the acid number is less than 5, the reaction is stopped.

[0347] In step b), in a 250 mL flask equipped with a magnetic stirrer, 100 g of the acidic oil obtained in a), 70 g of 3-Mercapto-1,2-propanediol (commercially available from Sigma Aldrich) and 5 g of 2-Hydroxy-2-methylpropiophenone (commercially available from Sigma Aldrich) are added to 15 mL of ethyl acetate and stirred for 5 minutes under argon. The reaction mixture is then irradiated under a UV lamp (100 W, 365 nm) for 4 hours and subsequently washed 3 times with saturated NaCl water. The organic phase is separated, dried over MgSO4, and then concentrated under vacuum. The solvent, traces of thiol, and photoinitiator (2-Hydroxy-2-methylpropiophenone) are removed by distillation under reduced pressure.

[0348] In step c), 100 g of the hydroxylated acid oil obtained in step b) and 100 g of tert-butyl acetoacetate are introduced into a 250 mL round-bottom flask equipped with a magnetic stirrer. The reaction mixture is heated to 130 °C using an oil bath. After 4 hours of reaction, the reaction mixture is placed under continuous vacuum for 1 hour. A viscous, brown-colored oil is obtained.

[0349] Example F: Synthesis of a castor oil with acetoacetate function (Compound No. 6)

[0350] The synthesis is represented by the following preparation scheme: Step a)#:

[0351]

[0353] In step a), in a 250 mL flask equipped with a magnetic stirrer, 100 g of castor oil (commercially available from Interchimie), 17 g of 3-Mercapto-1,2-propanediol (commercially available from Sigma Aldrich), and 1 g of 2-Hydroxy-2-methylpropiophenone (commercially available from Sigma Aldrich) are added to 20 mL of ethyl acetate and stirred for 5 minutes under argon. The reaction mixture is then irradiated under a UV lamp (100 W, 365 nm) for 4 hours and subsequently washed 3 times with saturated NaCl water. The organic phase is separated, dried over MgSO4, and then concentrated under vacuum. The solvent, traces of thiol and photoinitiator (2-Hydroxy 2-methylpropiophenone) are removed by distillation under reduced pressure.

[0354] In step b), 100 g of hydroxylated castor oil obtained in step a) and 99 g of tert-butyl acetoacetate are introduced into a 250 mL round-bottom flask equipped with a magnetic stirrer. The reaction mixture is then heated to 130 °C using an oil bath (set to 140 °C on the oil bath). After 4 hours, the reaction mixture is placed under continuous vacuum for 1 hour. A viscous, yellow-colored oil is obtained.

[0355] Example G: Synthesis of mannitol dihexanoate with acetoacetate function (Compound No. 7)

[0356] The synthesis is represented by the following preparation scheme: Step a)#: Step b)#:

[0358] , V" "T

[0359] In step a), mannitol dihexanoate is obtained from mannitol under the conditions described in the publication Angew. Chem. Int. Ed. 2010, 49, 7695-7698.

[0360] After 64 hours at 45°C, the reaction mixture was filtered and then concentrated under reduced pressure. The crude compound obtained after filtration and evaporation was then triturated in dichloromethane.

[0361] In step b), 4 equivalents of 2,2,6-Trimethyl-1,3-dioxin-4-one in p-xylene are heated at 140°C for 2 hours. Purification by silica gel chromatography leads to the compound mannitol dihexanoate with an acetoacetate function.

[0362] Example H: Synthesis of sucrose palmitate with acetoacetate function (Compound No. 8)

[0363] 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.

[0364] Example I: Synthesis of a castor oil with acetoacetate function (Compound No. 9)

[0365] The synthesis is represented by the following preparation scheme: Step a)#: Step c)#:

[0369] 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.

[0370] 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.

[0371] 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.

[0372] Examples J to R: Examples of compounds of formula (11)

[0373] Example J: Compound No. 11: K-FLEX 7301 marketed by KING industrie

[0374] Example K j. _ Compound No. 21 j. Glucose with acetoacetate function (5eq)

[0375] Compound 2' was synthesized according to the following scheme:

[0376] Scheme in which identical or different RI represents a hydrogen atom or a -methylcarbonylmethylcarbonyl group -C(O)-CH2-C(O)-CH3, it being understood that at least two RI radicals represent -C(O)-CH2-C(O)-CH3, in particular 5 RI radicals represent -C(O)-CH2-C(O)-CH3.

[0377] In a one-liter three-necked flask equipped with a mechanical stirrer and a distillation column, 100 g of D-glucose and 482.90 g of tert-butyl acetoacetate are introduced. The reaction mixture is heated in an oil bath (oil bath temperature 150°C–160°C) for 5 hours. After 5 hours, NMR confirms the grafting of the acetoacetate group. The reaction mixture is then concentrated using a rotary evaporator at 150°C under continuous vacuum. A highly viscous, dark brown liquid is obtained, which, upon analysis, corresponds to the expected product.

[0378] Example L: Compound No. 3 1 Mannose with acetoacetate function (5eq)

[0379] Compound 3' was synthesized according to the following scheme:

[0380] Scheme in which identical or different RI represents a hydrogen atom or a -C(O)-CH2-C(O)-CH3 group, it being understood that at least two RI radicals represent -C(O)-CH2-C(O)-CH3, in particular 5 RI radicals represent -C(O)-CH2 -C(O)-CH3.

[0381] In a one-liter three-necked flask equipped with a mechanical stirrer and a distillation column, 100 g of D-mannose and 482.90 g of tert-butyl acetoacetate are introduced. The reaction mixture is heated in an oil bath (oil bath temperature 140°C–150°C) for 5 h. After 5 h, NMR confirms the grafting of the acetoacetate group. The reaction mixture is then concentrated using a rotary evaporator at 150°C under continuous vacuum. A viscous yellow liquid is obtained, which, upon analysis, corresponds to the expected product.

[0382] Example M j. _ Compound No. 41 Xylitol with acetoacetate function (5eq)

[0383] Compound 4' was synthesized according to the following scheme:

[0384] Scheme in which identical or different RI represents a hydrogen atom or a -C(O)-CH2-C(O)-CH3 group, it being understood that at least two RI radicals represent -C(O)-CH2-C(O)-CH3, in particular 5 RI radicals represent -C(O)-CH2 -C(O)-CH3.

[0385] In a 500 mL three-necked flask equipped with a mechanical stirrer and a distillation column, 25 g of xylitol and 142.69 g of tert-butyl acetoacetate are introduced. The reaction mixture is heated in an oil bath (oil bath temperature 140°C–150°C) for 5 h. After 5 h, NMR confirms the grafting of the acetoacetate group. The reaction mixture is then concentrated using a rotary evaporator at 150°C under continuous vacuum. A highly viscous brown liquid is obtained, which, upon analysis, corresponds to the expected product.

[0386] Example N j. _ Compound No. 5 1 Sorbitol with acetoacetate function (6eq)

[0387] Compound 5' was synthesized according to the following scheme:

[0388] Scheme in which identical or different RI represents a hydrogen atom or a -C(O)-CH2-C(O)-CH3 group, it being understood that at least two RI radicals represent -C(O)-CH2-C(O)-CH3, in particular 6 RI radicals represent -C(O)-CH2 -C(O)-CH3.

[0389] In a one-liter three-necked flask equipped with a mechanical stirrer and a distillation column, 100 g of sorbitol and 573.20 g of tert-butyl acetoacetate are introduced. The reaction mixture is heated in an oil bath (oil bath temperature 140°C–150°C) for 5 h. After 5 h, NMR confirms the grafting of the acetoacetate group. The reaction mixture is then concentrated using a rotary evaporator at 150°C under continuous vacuum. A viscous, orange-yellow liquid is obtained, which, upon analysis, corresponds to the expected product.

[0390] Example O: Compound No. 6 1 Sorbitol with acetoacetate function (3eq)

[0391] Compound 6' was synthesized according to the following scheme:

[0392] Scheme in which identical or different RI represents a hydrogen atom or a -C(O)-CH2-C(O)-CH3 group, it being understood that at least two RI radicals represent -C(O)-CH2-C(O)-CH3, in particular 3 RI radicals represent -C(O)-CH2 -C(O)-CH3.

[0393] In a one-liter three-necked flask equipped with a mechanical stirrer and a distillation column, 100 g of sorbitol and 260.54 g of tert-butyl acetoacetate are introduced. The reaction mixture is heated in an oil bath (oil bath temperature 140°C–150°C) for 5 h. After 5 h, NMR confirms the grafting of the acetoacetate group. The reaction mixture is then concentrated using a rotary evaporator at 150°C under continuous vacuum. A viscous yellow liquid is obtained, which, upon analysis, corresponds to the expected product.

[0394] Example P: Compound No. 7 1 Dipentaerythritol with acetoacetate function (6eq)

[0395] Compound 7' was synthesized according to the following scheme:

[0396] Scheme in which identical or different RI represents a hydrogen atom or a -C(O)-CH2-C(O)-CH3 group, it being understood that at least two RI radicals represent -C(O)-CH2-C(O)-CH3, in particular 6 RI radicals represent -C(O)-CH2 -C(O)-CH3.

[0397] In a one-liter three-necked flask equipped with a mechanical stirrer and a distillation column, 50 g of dipentaerythritol and 195.33 g of tert-butyl acetoacetate are introduced. The reaction mixture is heated in an oil bath (oil bath temperature 140°C–150°C) for 4 hours. After 4 hours, NMR confirms the incorporation of the acetoacetate group. The reaction mixture is then concentrated using a rotary evaporator at 150°C under continuous vacuum. A viscous, orange-brown liquid is obtained, which, upon analysis, corresponds to the expected product.

[0398] Example 0: Compound No. 8 1 Pentaerythritol tetraacetoacetate

[0399] Compound 8' was synthesized according to the following scheme:

[0400] In a one-liter three-necked flask equipped with a mechanical stirrer and a distillation column, 100 g of Pentaerythritol and 510.89 g of Tert-butyl acetoacetate are introduced. The reaction mixture is heated using an oil bath (oil bath temperature 140°C-150°C) for 4 hours.

[0401] After 4 hours, NMR confirms the grafting of the acetoacetate group. The reaction mixture is then concentrated using a rotary evaporator at 150 °C under continuous vacuum. A translucent yellow viscous liquid is obtained, which, after analysis, corresponds to the expected product.

[0402] Example R: Compound No. 9 1 Sucrose with acetoacetate function (8eq)

[0403] Compound 9' was synthesized according to the following scheme:

[0404] Scheme in which identical or different RI represents a hydrogen atom or a -C(O)-CH2-C(O)-CH3 group, it being understood that at least two RI radicals represent -C(O)-CH2-C(O)-CH3, in particular 8 RI radicals represent -C(O)-CH2 -C(O)-CH3.

[0405] In a one-liter three-necked flask equipped with a mechanical stirrer and a distillation column, 100 g of sucrose and 406.55 g of tert-butyl acetoacetate are introduced. The reaction mixture is heated in an oil bath (oil bath temperature 140°C–150°C) for 4 hours. After 4 hours, NMR confirms the incorporation of the acetoacetate group. The reaction mixture is then concentrated using a rotary evaporator at 150°C under continuous vacuum. A viscous, orange-yellow liquid is obtained, which, upon analysis, corresponds to the expected product. Synthesis of the polyamine compound (la)

[0406] The compound (the) was synthesized according to the following scheme: OO ûAÀ-L / Ci ; $ $ ? aS . 5 J f . ;S ------'-------'. MW, H? H ' H ■■ H A 8 compound (the)

[0407] A solution of azelaic acid dichloride (11.9 mL, 59.2 mmol, 1 equiv.) in anhydrous CH2Cl2 (148 mL) is added dropwise to a solution of N-(tert-Butoxycarbonyl)-1,5-diaminopentane (Compound A) (24.7 g, 118 mmol, 2 equiv.) and N,N-Diisopropylethylamine (DIPEA) (21.9 mL, 124 mmol, 2.10 equiv.) in CH2Cl2 (148 mL) at 0°C. The ice bath is removed and the mixture is stirred at room temperature for 2 h. Water (200 mL) is added to the mixture and the volatiles are removed under reduced pressure. The resulting white solid is filtered and washed successively with water, a 10% aqueous solution of KHSO4, water, an aqueous solution of saturated NaHCO3, and finally water. The resulting white solid is dried in a desiccator under reduced pressure with P2O5 for approximately 24 hours to yield the crude product as a white solid.

[0408] The solid is triturated in diethyl ether, filtered, and washed twice with diethyl ether before being dried under reduced pressure to give compound B as a white solid (35.4 g). The solid is engaged in the next step without further purification.

[0409] HCl (4N in 1,4-dioxane, 296 mL, 1.18 mol, 20 equiv.) is added dropwise to a suspension of compound B (35.4 g, 59.2 mmol, 1 equiv.) in dioxane (592 mL), and the mixture is stirred at room temperature for 22 h. The solid is filtered and washed with diethyl ether (2 x 70 mL). This solid is resuspended in water (200 mL), and Amberlite IR78 (OH form) resin is added until pH 10-11 is reached. The resin The solid is removed by filtration and the filtrate is concentrated under reduced pressure to yield a white solid. The solid is resuspended in ethanol and the suspension is stirred for 1 hour at 50°C before being filtered. The filtrate is concentrated to yield a white solid.

[0410] The resulting white solid is dissolved in water (approx. 100 mL) and passed through an Amberlite IR78 (OH form) resin column. The product-containing fractions are collected and concentrated under reduced pressure, then co-evaporated twice with ethanol to give a white solid. The compound (la) is obtained in 90% yield in two steps. Synthesis of the polyamine compound (2a)

[0411] Compound (2a) was synthesized according to the following scheme:

[0412] N,N-Diisopropylethylamine (DIPEA) (544 mL, 3.12 mol, 6.00 eq.) is added to a citric acid solution (100.00 g, 0.51 mol, 1.00 eq.) in tetrahydrofuran (1041 mL) in a 4 L double-jacketed glass reactor with mechanical stirring. Acetonitrile (1050 mL) is then added to the gelatinous mixture. To the resulting homogeneous solution, 1,(3-Dimethylaminopropyl)-3-Ethylcarbodihnide hydrochloride (EDCI) (399.1 g, 2.08 mol, 4.00 eq.) and then 2-Hydroxypyridine 1-oxide (HOPO) (231.3 g, 2.08 mol, 4.00 eq.) are added. The reaction mixture is stirred at room temperature for 10 minutes, then a solution of N-(tert-Butoxycarbonyl)-1,5-diaminopentane (368.5 g, 1.82 mol, 3.50 eq.) in acetonitrile (200 mL) is added. The reaction mixture is heated at 50°C for 3 h. The reaction mixture is concentrated under vacuum. The resulting oil is reconstituted in ethyl acetate (1400 mL) and water (800 mL).The phases are separated and the organic phase is washed with water (800 mL), HCl IN (2 x 800 mL), NaHCO3 sat (2 x 800 mL) and brine (1 x 1600 mL). The organic phase is then dried over Na2SO4, filtered and concentrated under vacuum to obtain compound C (390 g, 96%) as a brown oil.

[0413] Hydrogen chloride (4M in dioxane) (1.70 L, 6.96 mol, 14.0 eq.) is added to a solution in 1,4-dioxane (1.30 L, 0.36 M) of compound C (390.0 g, 0.497 mol, 1.00 eq.) previously obtained in a 4 L double-jacketed glass reactor with mechanical stirring. The reaction mixture is stirred at 25 °C overnight. The supernatant is then removed by aspiration, and the remaining solid is dissolved in a methanol / water mixture (1.40 L, 9:1). The solution is filtered through Amberlite IRN-78 (-2 kg), and the resin is washed before use with 2 L of 2M NaOH, 3 L of water, and 3 L of methanol. The resulting filtrate is concentrated under vacuum and then resuspended in water (1.0 L). The solution is treated with activated carbon (100 g, until no further discoloration is observed) and then filtered through Celite buffer. The resulting filtrate is concentrated under vacuum to reduce the volume to approximately µL, and the solution is lyophilized for 3 days.The gum obtained is then dried under high vacuum at 50°C for 2 days to obtain compound (2a) with a yield of 86% in the form of a yellow gum.

[0414] The following compositions A1 to A6, B1 to B7, and REF1 and REF2 were prepared and then tested in Examples 1 to 10. Compositions A1 to A6

[0415] [Tables2] Ingredients Al A2 A3 A4 A5 A6 Compound 8' of example Q 10 Compound 9' of example R 10 Compound 7' of example P 10 10 Compound 9 of example I 29.5 Compound 7 of example G 13.7 Red Iron Oxide (CI: 7 7491) 12 12 12 12 Water / Ethanol (50 / 50) Qsp 100 Qsp 100 Qsp 100 Qsp 100 Qsp 100 Ethyl Lactate Qsp 100 Compositions B1 to B7

[0416] [Tables3] Ingredients B1 B2 B3 B4 B5 B6 B7 Polyamine compound (1 a) 7 14 7 11.3 7 7 Polyamine compound (3 a) 2.6 2.6 Polyamine compound (2 a) 12.6 6 Polylysine PL-25 (as a 25% wt. solution in water) Supplier: JNC 24 MA Water / Ethanol (50 / 50) Qsp 1 00 Qsp 1 00 Qsp 1 00 Qsp 1 00 Qsp 1 00 Ethyl Lactate Qsp 1 00

[0417] MA: Active Ingredient Reference compositions REF1 and REF2

[0418] [Tables4] Ingredients REF1 REF2 Solvent Water / Ethanol (50 / 50) Qsp 100 - Ethyl Lactate - Qsp 100

[0419] Examples 1 to 4: Hair application for curl relaxing Hair strands used

[0420] Strands of 2.7 g of natural hair with a length of 27 cm and exhibiting a type IV curl were used in examples 1 to 4. The strands were washed using two successive DOP shampoos (0.4 g / g of hair) before application of the compositions to be tested according to procedure 1 described below. Operating procedure 1

[0421] 1.08 g of the composition to be tested are applied to a wet wick. The wick is then combed and hung to dry at room temperature for 24 hours.

[0422] For each of the strands treated according to operating procedure 1, measurements of the length of the strand were taken before application of the composition to be tested and then after implementation of operating procedure 1, shampooing and drying at room temperature.

[0423] The compositions tested in examples 1 to 4 and the results of the evaluations are summarized in the table below.

[0424] [Tables5] Example Tested Composition Length of strand before application of the tested composition (cm) Length of strand after procedure 1 followed by shampooing then drying at room temperature (cm) Example 1 (Invention) Extemporaneous mixture Al / Bl 50 / 50 (weight in / weight) 21.5 26 Example 2 (Comparative) REF1 21.5 22 Example 3 (Invention) Extemporaneous mixture A2 / B7 50 / 50 (weight in / weight) 21.5 25 Example 4 (Comparative) REF2 21.5 22

[0425] The length of the strand treated according to Example 1 (invention) is greater than that measured on the strand of Example 2 (comparative), and the length of the strand treated according to Example 3 (invention) is greater than that measured on the strand of Example 4 (comparative). The process according to the present invention therefore makes it possible to obtain a high-quality curl relaxation.

[0426] Examples 5 to 10: Hair coloring application Hair strands used

[0427] Strands of natural hair that are 90% white were used in examples 5 to 10. Operating procedure 2 (Hair coloring)

[0428] 1 g of the composition to be tested is applied to a strand of dry hair. After After application, the hair is combed and dried with a hairdryer, then left to rest for 24 hours at room temperature.

[0429] Each of the strands is treated according to operating procedure 2 and then subjected to a repeated shampooing test in order to evaluate the tenacity (the persistence) of the colour obtained with shampooing.

[0430] The persistence of the shampoo strand colouring was evaluated in the CIE L*a*b* system, using a Minolta Spectrophotometer CM3600A colourimeter (illuminant D65, angle 10°, specular component included).

[0431] 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.

[0432] The color permanence is assessed by the color difference AE between the colored strands before shampooing, and then after 15 shampoos. The lower the AE value, the more the color persists through shampooing. The AE value is calculated according to the following equation: ae = ■ L vy ■ yr - V * av • V

[0433] In this equation, L*, a* and b* represent the values ​​measured after hair coloring and after undergoing 15 shampoos, and Lo*, a0* and b0* represent the values ​​measured after hair coloring but before shampooing.

[0434] The compositions tested in examples 5 to 10 and the results of the evaluations are summarized in the table below.

[0435] [Tableauxô] Example Composition tested Number of shampoos L* a* b* AE Example 5 (Invention) Customary external mixture A3 / B 2 50 / 50 (weight / weight) 0 30.14 24.48 16.12 6.58 15 34.74 20.45 13.68 Example 6 (Invention) Customary external mixture A4 / B 3 50 / 50 (weight / weight) 0 32.03 23.69 15.13 9.13 15 38.49 17.89 12.29 Example 7 (Invention) Customary external mixture A5 / B 4 50 / 50 (weight / weight) 0 30.9 24.74 16.12 2.23 15 33.03 24.93 16.75 Example 8 (Invention) Temporary external mixture A6 / B 5 0 30.48 26.51 18.54 8.28 50 / 50 (weight / weight) 15 36.74 22.08 15.41 Example 9 (Invention) Temporary external mixture A3 / B 3 50 / 50 (weight / weight) 0 30.89 24.4 15.92 8.79 15 36.96 18.95 12.64 Example 10 (Invention) Temporary external mixture A4 / B 6 50 / 50 (weight / weight) 0 32.3 24.59 16.24 2.75 15 31.75 22.44 14.62

[0436] The coloring process according to the present invention makes it possible to obtain a hair color with very good permanence up to 15 shampoos.

Claims

Demands

1. A process for treating keratin fibers using the following on the keratin fibers: (i) one or more compounds A chosen from among the compounds of formula (I) and / or (!'), their optical isomers, their geometric isomers, their salts, their solvates such as hydrates, and their mixtures: (H)p™Z^ [(O)r(AKl ) q ~(OC(O )-C(R s (Rb)~C(O)-R4)u] !3 Formula (I) 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 groups or heteroatoms chosen from -O-, -N(Ra)-, -S-, -C(O)-, (hetero)cycles, and 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 C1-C40, 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)-, (hetero)cycle(s), and their combinations, in particular -OC(O)-, -C(O)-O- and / or -(hetero)cycle-O-(hetero)cycle-; - AK3 represents a linear or branched divalent hydrocarbon chain saturated or unsaturated at C1-C12, preferably at Ci-C6, more preferentially saturated at Ci-C6, even more preferentially at C1-C4; - R represents a hydrogen atom, a linear or branched alkyl radical 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 (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; Formula (!') in which: - R1 represents a versatile hydrocarbon radical in C2 to CM, linear or branched, saturated or unsaturated, conjugated or not, acyclic or cyclic, aromatic or not, R1 being further: a) possibly substituted by one or more hydroxy groups OH, dialkylamino-N(R)2 with R representing a (Ci-C4)alkyl group, carboxy-C(O)-OH, a vinyl group, and / or b) possibly interrupted by one or more heteroatoms or groups selected from O, S, carbonyl -C(O)-, amine -N(R'), or their associations, in which R' represents a hydrogen atom, a linear or branched alkyl group having from 1 to 4 carbon atoms possibly substituted by at least one hydroxy group (OH) or possibly substituted by -XC(O)-C(Ra)(Rb)-C(O)-R2; - R2 represents a monovalent hydrocarbon radical in C1 to C6, linear or branched, saturated or unsaturated; - Ra, and Rb, identical or different, represent a hydrogen atom or a (CrC4)alkyl group; - X is a heteroatom or group chosen from O, S, N(R') or , -S-CH2-C(O)-O-, -OC(O)-CH2-S-, -OC(O)-N(R')-, -N(R')-C(O)-O-, -N(R')-C(O)-N(R')-, R' being as defined above; - n denotes an integer ranging from 2 to 10, particularly from 3 to 9;(ii) one or more polyamine compounds B selected from compounds of formula (II), their optical isomers, their geometric isomers, their salts, their solvates such as hydrates, and their mixtures: H2N—T—NH2 (II) Formula (II) in which T represents a divalent hydrocarbon group, linear or branched, saturated or unsaturated, preferably saturated, comprising from 4 to 22 carbon atoms, optionally substituted by an -NH2 group, the T group being substituted by one or more hydroxyl (-OH) groups and / or interrupted by one or more groups selected from -C(O)-, -NRa- or their combinations such as -NRa-C(O)- or -C(O)-NRa-, with Ra representing a hydrogen atom or a (Ci-C4)alkyl group; and iii) possibly one or more coloring agents selected from pigments, direct dyes, and mixtures thereof, preferably from pigments.;

2. A method according to claim 1, wherein the compound(s) A are selected from the compounds of formula (I), their optical isomers, their geometric isomers, their solvates such as hydrates, and their mixtures, 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-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)-, 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 for formula (I) in claim 1; provided that the compounds of formula (I) contain at least 2 -C(O)-C(Ra)(Rb)-C(O)-R4 radicals; preferably from the following compounds (1), (2), (3), (4), (7), (8), (9), (11) and (16), their optical isomers, geometric isomers, their solvates such as hydrates, and mixtures thereof: (1)

3. more preferentially among compound (16), its optical isomers, its geometric isomers, its solvates such as hydrates, and their mixtures. A method according to claim 1, wherein the compound(s) A are selected from compounds of formula (I), their optical isomers, their geometric isomers, their solvates such as hydrates, and their mixtures, such as: - p is equal to 1; - Z represents a multivalent hydrocarbon radical in C2 to C24, particularly in C4 to C20, preferably in C5 or 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-(O-C(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 Ci0-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 such as defined for formula (I) in claim 1, preferably X denotes 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; provided that the compounds of formula (I) contain at least 2 C(O)-C(Ra)(Rb)-C(O)-R4 radicals; preferably from compounds (12) and (15) below, their optical isomers, their geometric isomers, their solvates such as hydrates, and their mixtures: more preferentially among compound (15), its optical isomers, its geometric isomers, its solvates such as hydrates, and their mixtures.

4. A method according to claim 1, wherein the compound(s) A are chosen from compounds of formula (I), their optical isomers, their geometric isomers, their solvates such as hydrates, and their mixtures, such as: - p is equal to 0; - m is non-zero; - Z represents a divalent hydrocarbon radical in the C2 to C24 range, particularly in the C3 to C2 range, 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 selected 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 C14-C30, preferably in C14-C24, preferably in C15, said chain being optionally substituted by one or more identical or different radicals selected from -OR and -X-AK3-(O-C(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 such as defined previously for formula (I), and preferably X designates 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 the compounds of formula (I) contain at least 2 C(O)-C(Ra)(Rb)-C(O)-R4 radicals.;

5. A method according to claim 1, wherein the compound(s) A are selected from the compounds of formula (l'a), their optical isomers, their geometric isomers, their salts, their solvates such as hydrates, and their mixtures: (l'a) | VQ; Formula (l'a) in which: - R1 is as defined for formula (!') in claim 1, particularly represents a C2 to Cm hydrocarbon polyvalent radical, preferably C3-C12, preferably C4-C10, linear or branched, saturated or unsaturated, conjugated or not, acyclic or cyclic, aromatic or not, R1 being further: a) optionally substituted by one or more hydroxy groups OH, and / or b) optionally interrupted by one or more heteroatoms or groups selected from O, S, -N(R'), preferably interrupted by one or more oxygen atoms in which R' is as defined for formula (!') in claim 1; - R2 is as defined for formula (!') in claim 1, preferably R2 represents a (Ci-C6)alkyl group, linear or branched, preferably a (Ci-C4)alkyl group more preferably methyl or tert-butyl such as methyl; and - n is as defined for formula (!') in claim 1, preferably n denotes an integer from 2 to 9.

6. A method according to claim 1 or 5, wherein the compounds of formula (!') or (l'a) are such that: R1 represents a C6-C8 hydrocarbon polyvalent radical, linear or branched, unsaturated monocyclic or bicyclic, preferably monocyclic, and aromatic such as phenyl; or R1 represents a C5-Ci2 hydrocarbon polyvalent radical, saturated monocyclic or bicyclic, optionally interrupted by one or more heteroatoms or groups selected from O, S, -N(R'), wherein R' represents a hydrogen atom, an alkyl group having from 1 to 4 carbon atoms, preferably interrupted by one or more oxygen atoms; preferably R1 represents a monosaccharide or polysaccharide motif, in particular a disaccharide, on which n hydroxyl groups have been substituted by n -OC(O)-CH2-C(O)-R2 groups with R2 and n as defined for formula (!') or (l'a) in claim 1 or 5;or R1 represents a versatile acyclic hydrocarbon radical in C2 to Ci2, preferably in C3-C10, linear or branched, saturated or unsaturated, preferably saturated.;

7. 7. A method according to claim 1, 5 or 6, wherein the compounds of formula (!') or (l'a) are such that n denotes an integer from 2 to 9, more particularly n denotes an integer from 3 to 9, even more particularly n denotes an integer from 4 to 9.

8. 8. A method according to claim 1, wherein the compound(s) A are selected from the following compounds, their optical isomers, their salts, their solvates such as hydrates, and mixtures thereof: (Compound) “CAS Chemical Structure 700865-73-2 Ackq-1 4-(1,7-heptanediyl) butanoic acid ester <• $ C- C> (27 63233S-20-0 3-gxo-14'-(1,8-octanediyl) butanoic acid ester (27 501426-98-8 3-0X0-14 Ah 10-decanediyl) butanoic acid ester . ..To x . .. To x -■■' ''O' ■■ " x ■■To x (47 174498-06-7 3-0X04440-propanediyl) butanoic acid ■Ç? '•f (.57 160187-62-0 3-oxo-1,2-dimethyl-1,2-ethanediyl ester of butanoic acid * 6 o (®7 Î45020-19-5 3-üxa-2-butyi-2-ethib 1,3-propanediyl ester of butanoic acid (77 87530-36-7 3-oxo-tt,22-îétramethyi-1,2-ethanediyt ester of butanoic acid / \, 4 >:• (87 58213-75-5 3-oxa-1,14 1-methyl-1,3-propanediyt) ester of butanoic acid & C: ; <5 {'Compound) Chemical name; Chemical structure (9') 58213-74-4 3-0X0-1.1'42,2- dimethyM-(1-methylethyl-1,3-prapacediyil butaocffc acid ester 9 A.,- ' AïA 1 x^. v .. v<: . v„... v Y\ {W} 39564-28-8 3-oxch1,1'41,5-perstanediyi) butanoic acid ester AA ., ... ... J v-“ . P.2') 43018-41-2 3-oxo-1,4-butanediyl ester of butanoic acid 0 Ci .1 1 ... ... ... ... ■ ' " TA (13'} 6079-90-9 3--üxo-1 methvM.2 ethanediyl ester of butanaic acid <5 G 1 I ........ .. . " TYY ' 0 8 {14'} 5459-04-1 3-oxo-1,2-ethanediyl ester of butanaic acid 0 A / L,. ......... I Ô 2388-18-3 3-cxo-1,7-(1..6-hexanediyl) ester of butanaic acid 3-oxo-1,6-hexanediyl ester of butanoic acid (90!) t .Î ... . o. ... ... . -v^,, .■ YC: {Component} Chemical Name Chemical structure (W) 32818-60-3 bis(3-œcobutanoate) of 1,1-^2-8^(1,3. dioxobutaxytaêthyi}-1,3-propanediyf] % V----5 / >1j' 51980-20-2 bis^axobulanoate j of 1,142,2-Bis(hydroxymelhyi)-1,3-propanediyi] '0' (18') 0 Hi § y---OH —z 1 0 0 130973-05-05-6 ester^ 3,zè-gxo- butanolque JUL x'.y' x (2G3 139264-86-1 3-dxo-12;4- benzeneiriy 1 butanoic acid acid 1 î " X If î AAA 'x--x Ar " Az' ''•'Z' (Compound) Chemical structure .22208-25-9 Triacetoacetate of trimeftylpropane K-FLEX 7301 X?' o OXX 'X."" (22') 2360524-48- ¢. xv--' 'Xy .,•■■"VX*' (23') 66229-33-2 3-oxo-2-butyF2-[(1,3-dioxobutoxy jmethylO-1.3-propanediyl butanoic acid ester § il x—x <5 V s (24') 1579231-50- 4.4-dsmethyl- 3-oxo-. V42;2-bisK4,4-dimethylM ,3-dioxoperty IJcsxyJmeth yiH ,3-propaediyl] pentanoic acid ester, --7—— $ ta \______ (25'J 6079-98-7 Ida(3-nxobüÆarioate) de propanotryi: G lè 4 x\. „Jk gXfGçjæPSA® N'CASE: 6464646464^ (26') tWa-àcêtoaCétate de meso-erylhBtol '"TQ ozv—' / 1 zv v '4 V (27'} 169533-29-œ3 aD-Gkose 1,2,3,4:6-per:takis(3-cxabutanoate) T y .-a T ft a'K ■>.• 4<.'.v, A. « rs -?■'■' G ' "«s" v AA / À 'AA A CJ- x {28-7} -5^25-2 3,4-iris-O-(1,3-dioxobuiy ))-D-xytopyranosyijoxÿj-d'adde benzoic .Tl ï vr ■ 'A '--A g '5 A' 5 A. A„ 4A A " ■ r XI - <■< 9} m-1 (29- 2,3,4,6-tetracjs(3-oxobuiapoate) of aD-GisJcopys'anQside, 1 ,3;4,6-tetrac®-O-(1,3-d)oxobJJty!}-pD-fructofuranosyt 11 A'y 6" ;\a'.'!.... Maza AZ'|| g | "A"'l >\ y (Compound) NOPt chi:Tiq-o Chemical structure (30) 964S1 -28-' D-<3tucopyranose, perAkisG-oxobutanoate) "aA'' Vx..--'' 2.54ms(3-©xobutanoate) (32') 2254710-49- x--'-.. ■ ??A< (33') sorbstoE hexa-acetoacetate ' 0 0; ¢-- A,-- A. ' o ... -5 i ï v' A 7 ■. ■■ ■. cccy? <J A, ..A <? "CAS chemical formula: Chemical structure (34') D-Giucitci, 4-OpD- / 216756-88-7 gaiactopyranosyl-. 0 0—RT pdÿacetoacetate RI —û......<' V.....3 o.....ri \....... / / Z s % / \ J- 7 / \ Sî 0 SW K. with RI chosen from -G (0 )- G Hz-C (G j-CHs.. H with at least two radicals RI represent -CfO )-C Hz-C (Q )-C Hs (35') Sucrose, À --'• '' '' W1656-52-1 pdÿacetoacetate \ z '51 „ ÇT'” l' with R1 chosen from -CfCJ-CHs-QiCf^CHs, H with at least two radicals R1 represent -C(Gj-CH2-C(O)-ÜHs (38) G^JCCSê / pdÿacetoacetate 7-J / \ G Rï {Compound} N® CAS bionvehimique Mannose poiyacetoacetate {40'} Xyistof poiyacêtoacetate poiyacétoaceiate A1 Three RI radicals represent -C(O)-CH2-C(O)-CH3; and three RI radicals represent a hydrogen atom <CÀS: Nom ctMrniqtié; Structure-chirétique ^47^.94.9 0 G A 1 A , " Y Y ï 2552-36-5 J H- ■ ■ II O f? {«H 139614-56-5 1 / XX X'x' 8 H {44’J 96169-30-1 • X-*' 'v" ’•■■■' s - ■ ’ 'y" 'T' <45'J 76839-01 -9 Y X’”'- x>!'' {48'} DfpentaeryÉhfiioi poîyacétoacetate ? 5 ' 'Xs' preferably 5 or 6 R1 radicals, more preferably 6 RI radicals represent -C{O)-CH2-G(Q>GH= in which identical or different RIs represent a hydrogen atom or a -C(O)-CH2-C(O)-CH3 group, it being understood that at least two RI radicals represent -C(O)-CH2-C(O)-CH3, preferably at least three RI radicals represent -C(O)-CH2-C(O)-CH3; preferably from among the compounds (16'), (18'), (21'), (35'), (36'), (37'), (38'), (39'), (40') and (46'), their optical isomers, their salts, their solvates such as hydrates, and their mixtures; more preferentially among the compounds (16'), (21'), (35'), (38'), (39') and (46'), their optical isomers, their salts, their solvates such as hydrates, and their mixtures; even more preferentially among the compounds (16'), (35') and (46'), their optical isomers, their salts, their solvates such as hydrates, and their mixtures.

9. A method according to any one of the preceding claims, wherein T represents a divalent, linear or branched, saturated hydrocarbon group comprising from 4 to 22 carbon atoms, preferably from 10 to 22 carbon atoms, more preferably from 15 to 20 carbon atoms, optionally substituted by an -NH2 group, the group T being interrupted by one or more groups selected from -C(O)-, -NRa- or their combinations such as -NRa-C(O)- or -C(O)-NRa-, Ra being as defined for formula (II) in claim 1, preferably interrupted by one or more groups selected from -NRa-C(O)- or -C(O)-NRa-, Ra being as defined for formula (II) in claim 1 and the group T being optionally substituted by one or more hydroxyl (-OH) groups;preferably T represents a divalent, linear or branched, saturated hydrocarbon group comprising 10 to 22 carbon atoms, preferably 15 to 20 carbon atoms, optionally substituted by an -NH2 group, the T group being interrupted by 2 or 3 groups selected from -NH-(CO)- or -(CO)-NH- and the T group being optionally substituted by one or more hydroxyl groups (-OH), in particular a hydroxyl group (-OH).;

10. A method according to any one of claims 1 to 8, wherein T represents a divalent, linear or branched, saturated hydrocarbon group comprising from 4 to 22 carbon atoms, preferably from 4 to 15 carbon atoms, more preferably from 4 to 10 carbon atoms, substituted by one or more hydroxyl (-OH) groups.

11. A method according to any one of claims 1 to 8, wherein the polyamine compound(s) B are selected from the following compounds (1a), (2a) and (3a), their optical isomers, their salts, their solvates such as hydrates, and mixtures thereof: (there)

12.

13.

14.

15. A method according to any one of the preceding claims, wherein the method is a method for permanently shaping keratin fibers, preferably a method for relaxing loops and / or smoothing keratin fibers. A method according to any one of claims 1 to 11, wherein the method is a method for coloring keratin fibers using on the keratin fibers one or more coloring agents selected from pigments, direct dyes, and mixtures thereof, preferably from pigments. A process according to any one of the preceding claims, wherein the process comprises applying to keratin fibers a composition (C) comprising the compound(s) A as defined in any one of claims 1 to 8, the polyamine compound(s) B as defined in any one of claims 1 or 9 to 11 and optionally one or more coloring agents selected from pigments, direct dyes, and mixtures thereof, preferably from pigments. A method according to the preceding claim, wherein: ■ The compound(s) A are present in composition (C) in a total content ranging from 0.2% to 80% by weight, preferably ranging from 0.5% to 50% by weight, more preferably ranging from 2% to 35% by weight, relative to the total weight of composition (C); and / or ■ The polyamine compound(s) B are present in composition (C) in a total content ranging from 0.2% to 60% by weight, preferably ranging from 0.5% to 40% by weight, more preferably ranging from 1% to 35% by weight, relative to the total weight of the composition (C).

16. A method according to any one of the preceding claims, wherein the keratin fibers are curly, crimped, or frizzy keratin fibers.

17. Composition (C) comprising the compound(s) A as defined in any one of claims 1 to 8, the polyamine compound(s) B as defined in any one of claims 1 or 9 to 11 and optionally one or more coloring agents selected from pigments, direct dyes, and mixtures thereof, preferably from pigments.

18. A two- or three-compartment device comprising: - a first compartment containing a composition (A) comprising the compound(s) (A) as defined in any one of claims 1 to 8 and optionally one or more coloring agents selected from pigments, direct dyes, and mixtures thereof, preferably from pigments; - a second compartment separate from the first compartment containing a composition (B) comprising the polyamine compound(s) B as defined in any one of claims 1 or 9 to 11 and optionally one or more coloring agents selected from pigments, direct dyes, and mixtures thereof, preferably from pigments;and - possibly a third compartment separate from the first and second compartments containing a composition comprising one or more coloring agents selected from pigments, direct colorants, and mixtures thereof, preferably from pigments.;

19. Use of one or more compounds A as defined in any one of claims 1 to 8 associated with one or more polyamine compounds B as defined in any one of claims 1 or 9 to 11 or of a composition (C) comprising the compound(s) A as defined in any one of claims 1 to 8 and the polyamine compound(s) B as defined in any one of claims 1 or 9 to 11, for the relaxation of loops and / or the smoothing of keratin fibers.

20. Use of one or more compounds A as defined in any one of claims 1 to 8 associated with one or more polyamine compounds B as defined in any one of claims 1 or 9 to 11 and one or more coloring agents selected from pigments, direct dyes, and mixtures thereof, preferably from pigments or of a composition (C) comprising compound(s) A as defined in any one of claims 1 to 8, polyamine compound(s) B as defined in any one of claims 1 or 9 to 11 and coloring agent(s) selected from pigments, direct dyes, and mixtures thereof, for coloring keratin fibers.

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