Use of a compound containing acetoacetate functions, optionally combined with a (POLY)amine compound, or of a composition comprising same, for protecting keratin fibers from moisture

Abstract

The present invention relates to the use of at least one compound containing acetoacetate functions, optionally combined with at least one (poly)amine compound or of a composition comprising same, for protecting keratin fibers from moisture.

Description

USE OF A COMPOUND CONTAINING ACETOACETATE FUNCTIONS, OPTIONALLY COMBINED WITH A (POLY)AMINE COMPOUND, OR OF A COMPOSITION COMPRISING SAME, FOR PROTECTING KERATIN FIBERS FROM MOISTURETECHNICAL FIELD OF THE INVENTION

[0001] The present invention relates to the use of at least one compound containing acetoacetate functions, optionally combined with at least one (poly)amine compound or of a composition comprising same, for protecting keratin fibers from moisture.BACKGROUND OF THE INVENTION

[0002] Due to their nature, certain hair types are more sensitive to humidity and may thus have a tendency to form frizziness, which may result in an increase in the volume of the head of hair. These hair types are particularly difficult to style in a humid environment.

[0003] In order to remedy this, it is common practice to use hair compositions based on silicone starting materials, which may however leave the hair looking greasy and feeling heavy, or based on oils, the conditioning effect of which may tend to fade rapidly over time by notably being sparingly resistant to external attacking factors, in particular shampoo.

[0004] Moreover, the formulation of environmentally-friendly cosmetic products, i.e. products whose design and development take account of environmental issues, is becoming a major preoccupation for contributing toward meeting the global challenges. It thus proves essential to propose more sustainable compositions, thereby enabling these environmental challenges to be met notably by reducing the use of compounds of petrochemical origin.

[0005] Thus, there is a real need to find a means of remedying these drawbacks, notably to facilitate hairstyling in a humid environment by durably limiting the formation of frizziness and / or the increase in volume of the head of hair in a humid environment, the observed effect being notably persistent on shampoo washing at least once.

[0006] The Applicant has discovered, surprisingly, that all or some of these objectives can be met by using at least one compound containing acetoacetate functions, optionally combined with at least one (poly)amine compound, or of a composition comprising same, for protecting keratin fibers from moisture.SUMMARY OF THE INVENTION

[0007] One subject of the present invention is the use of one or more compounds A optionally combined with one or more (poly)amine compounds or of a composition (C) comprising the compound(s) A and optionally the (poly)amine compound(s), for protecting keratin fibers from moisture, preferably for limiting the formation of frizziness and / or the increase in volume of the head of hair in a humid environment, the compound(s) A being chosen from the compounds of formula (I), the optical or geometrical isomers thereof, the solvates thereof, such as hydrates, and mixtures thereof: (I)in which formula (I):- Z represents a linear or branched, saturated or unsaturated, conjugated or non-conjugated, acyclic or cyclic, aromatic or non-aromatic multivalent C2to C40, in particular C3to C36, hydrocarbon-based radical, Z possibly being interrupted with one or more groups or heteroatoms chosen from -O-, -N(Ra)-, -S-, -C(O)-, (hetero)cycles, and combinations thereof;- AK1 represents a divalent saturated or unsaturated, linear or branched C1-C12, preferably C1-C6, more preferentially saturated C1-C6, hydrocarbon-based chain;- AK2 represents a linear or branched, saturated or unsaturated, C1-C40monovalent hydrocarbon-based chain, optionally substituted with one or more identical or different radicals chosen from -OR, -X-AK3-(O-C(O)-C(Ra)(Rb)-C(O)-R4)v; and / or said chain being optionally interrupted with one or more heteroatoms or groups chosen from -O-, -S-, -C(O)-, (hetero)cycle(s), and combinations thereof, in particular -O-C(O)-, -C(O)-O- and / or -(hetero)cycle-O-(hetero)cycle-;- AK3 represents a divalent linear or branched, saturated or unsaturated C1-C12, preferably C1-C6, more preferentially saturated C1-C6, even more preferentially C1-C4, hydrocarbon-based chain;- R represents a hydrogen atom, a linear or branched, saturated or unsaturated C1-C6, preferably C1-C4, alkyl radical, in particular a methyl radical, or a radical -C(O)-C(Ra)(Rb)-C(O)-R4;- X represents -O-, -S-, -O-C(O)- or -C(O)-O-;- Y represents -O-C(O)- or -C(O)-O-;- R4represents a linear or branched, saturated or unsaturated C1-C6monovalent hydrocarbon-based radical, preferably a (C1-C4)alkyl group, in particular methyl or tert-butyl, more preferentially methyl;- Raand Rb, which may be identical or different, represent a hydrogen atom or a (C1-C4)alkyl group, preferably a hydrogen atom;- p denotes an integer equal to 0 or 1;- m denotes an integer equal to 0, 1, 2, 3 or 4; it being understood that when m is greater than 1, then the radicals -Y-AK2are 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-(AK1)q-(O-C(O)-C(Ra)(Rb)-C(O)-R4)uare identical or different;- t 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 groups -C(O)-C(Ra)(Rb)-C(O)-R4.

[0008] DETAILED DESCRIPTION OF THE INVENTION

[0009] For the purposes of the present invention and unless otherwise indicated:

[0010] ▪ the term “keratin fibers” means fibers of human or animal origin, such as head hair, bodily hairs, the eyelashes, the eyebrows, wool, angora, cashmere or fur. According to the present invention, the keratin fibers are preferably human keratin fibers, more preferentially the head hair.

[0011] ▪ the term “(hetero)aryl” means aryl or heteroaryl groups.

[0012] ▪ the term “(hetero)cycloalkyl” means cycloalkyl or heterocycloalkyl groups.

[0013] ▪ the “aryl” or “heteroaryl” radicals or the aryl or heteroaryl part of a radical may be substituted with at least one substituent borne by a carbon atom, chosen from:- a C1-C6and preferably C1-C4(poly)(hydroxy)alkyl radical;- a halogen atom such as chlorine, fluorine or bromine;- a hydroxyl group;- a C1-C2alkoxy radical; a C2-C4(poly)hydroxyalkoxy radical;- an amino radical;- an amino radical substituted with one or two identical or different C1-C6, preferably C1-C4, alkyl radicals;- an acylamino radical (-N(R)-C(O)-R’) in which the radical R is a hydrogen atom;- a C1-C4alkyl radical and the radical R’ is a C1-C4alkyl radical; a carbamoyl radical ((R)2N-C(O)-) in which the radicals R, which may be identical or different, represent a hydrogen atom or a C1-C4alkyl radical;- an alkylsulfonylamino radical (R’-S(O)2-N(R)-) in which the radical R represents a hydrogen atom or a C1-C4alkyl radical and the radical R’ represents a C1-C4alkyl radical, or a phenyl radical;- an aminosulfonyl radical ((R)2N-S(O)2-) in which the radicals R, which may be identical or different, represent a hydrogen atom or a C1-C4alkyl radical;- a carboxylic radical in acid or salified (preferably with an alkali metal or a substituted or unsubstituted ammonium) form;- a cyano group (CN);- a polyhalo(C1-C4)alkyl group, preferentially trifluoromethyl (CF3).

[0014] ▪ the cyclic or heterocyclic part of a non-aromatic radical may be substituted with at least one substituent borne by a carbon atom, chosen from the following groups:- hydroxyl;- C1-C4alkoxy, C2-C4(poly)hydroxyalkoxy;- alkylcarbonylamino ((R-C(O)-NR’-), in which the radical R’ is a hydrogen atom or a C1-C4alkyl radical and the radical R is a C1-C2alkyl radical, amino substituted with one or two identical or different C1-C4alkyl groups;- alkylcarbonyloxy ((R-C(O)-O-), in which the radical R is a C1-C4alkyl radical, amino substituted with one or two identical or different C1-C4alkyl groups;- alkoxycarbonyl ((R-O-C(O)-) in which the radical R is a C1-C4alkyl radical, amino substituted with one or two identical or different C1-C4alkyl groups;

[0015] ▪ a cyclic or heterocyclic radical, or a non-aromatic part of an aryl or heteroaryl radical, may also be substituted with one or more oxo groups.

[0016] ▪ a hydrocarbon-based chain is unsaturated when it includes one or more double bonds and / or one or more triple bonds.

[0017] ▪ an “aryl” radical represents a monocyclic or fused or non-fused polycyclic hydrocarbon-based group comprising from 6 to 14 carbon atoms, and at least one ring of which is aromatic; preferentially, the aryl radical is a phenyl, biphenyl, naphthyl, indenyl, anthracenyl or tetrahydronaphthyl.

[0018] ▪ a “heteroaryl” radical represents a monocyclic or fused or non-fused polycyclic, 5- to 14-membered group, comprising from 1 to 6 heteroatoms chosen from nitrogen, oxygen, sulfur and selenium atoms, and at least one ring of which is aromatic; preferentially, a heteroaryl radical is chosen from acridinyl, benzimidazolyl, benzobistriazolyl, benzopyrazolyl, benzopyridazinyl, benzoquinolyl, benzothiazolyl, benzotriazolyl, benzoxazolyl, pyridyl, tetrazolyl, dihydrothiazolyl, imidazopyridyl, imidazolyl, indolyl, isoquinolyl, naphthoimidazolyl, naphthooxazolyl, naphthopyrazolyl, oxadiazolyl, oxazolyl, oxazolopyridyl, phenazinyl, phenoxazolyl, pyrazinyl, pyrazolyl, pyrilyl, pyrazoyltriazyl, pyridyl, pyridinoimidazolyl, pyrrolyl, quinolyl, tetrazolyl, thiadiazolyl, thiazolyl, thiazolopyridyl, thiazoylimidazolyl, thiopyrylyl, triazolyl and xanthylyl.

[0019] ▪ a “cyclic” or “cycloalkyl” radical is a monocyclic or fused or non-fused polycyclic, non-aromatic cyclic hydrocarbon-based radical containing from 5 to 14 carbon atoms, which may include one or more unsaturations; the cycloalkyl is preferably a cyclohexyl group.

[0020] ▪ a “heterocyclic” or “heterocycloalkyl” radical is a monocyclic or fused or non-fused polycyclic 3- to 9-membered non-aromatic cyclic radical, including from 1 to 4 heteroatoms chosen from nitrogen, oxygen, sulfur and selenium atoms; preferably, the heterocycloalkyl is chosen from epoxide, piperazinyl, piperidyl, morpholinyl and dithiolane.

[0021] ▪ an “alkyl” radical is a linear or branched, in particular C1-C6and preferably C1-C4saturated hydrocarbon-based radical.

[0022] ▪ an “alkoxy” radical is an alkyl-oxy radical for which the alkyl radical is a linear or branched C1-C6and preferentially C1-C4hydrocarbon-based radical.

[0023] ▪ a “(poly)(hydroxy)alkyl” radical denotes a C1-C6and preferably C1-C4alkyl radical optionally substituted with one or more hydroxyl radicals, preferably substituted with from 1 to 4 hydroxyl groups, more particularly between 1 and 3.

[0024] ▪ the “solvates” represent hydrates and also the combination with linear or branched C1-C4alcohols such as ethanol, isopropanol or n-propanol.

[0025] The expressions “between … and …”, “comprises from … to …”, “formed from … to …” and “ranging from … to …” should be understood as being inclusive of the limits, unless otherwise specified.

[0026] The terms “at least one” and “one or more” are synonymous and may be used interchangeably.Use

[0027] One subject of the present invention is the use of the compound(s) A as defined previously, optionally combined with one or more (poly)amine compounds or of a composition (C) comprising the compound(s) A and optionally one or more (poly)amine compound(s), for protecting keratin fibers from moisture, preferably for limiting the formation of frizziness and / or the increase in volume of the head of hair in a humid environment.

[0028] The Applicant has found, surprisingly, that the compound(s) A, optionally combined with one or more (poly)amine compounds, or the composition (C) comprising same, make it possible to facilitate the styling of keratin fibers in a humid environment and notably to limit the formation of frizziness and / or the increase in volume of the head of hair in a humid environment, it being possible for the observed effect to persist on shampoo washing at least once.

[0029] According to a first particular embodiment, the compound(s) A are used alone, i.e. not combined with one or more (poly)amine compounds, or the composition (C) does not comprise any (poly)amine compound.

[0030] According to a second particular embodiment, the compound(s) A are used in combination with one or more (poly)amine compounds.

[0031] According to this second particular embodiment, the (poly)amine compound(s) are preferably applied to the keratin fibers before, after or at the same time as the compound(s) A.

[0032] Alternatively, according to this second particular embodiment, the (poly)amine compound(s) may be applied to the keratin fibers before the compound(s) A.

[0033] Alternatively, according to this second particular embodiment, the (poly)amine compound(s) may be applied to the keratin fibers after the compound(s) A.

[0034] According to this second particular embodiment, the (poly)amine compound(s) may be included in a composition (B) which is separate from composition (C) comprising the compound(s) A, composition (B) preferably being applied to the keratin fibers before, after or at the same time as composition (C). Alternatively, according to this second particular embodiment, composition (B) may be applied to the keratin fibers before composition (C). Alternatively, according to this second particular embodiment, composition (B) may be applied to the keratin fibers after composition (C).

[0035] According to another particular embodiment, composition (C) comprises the compound(s) A and one or more (poly)amine compounds.

[0036] According to this other particular embodiment, composition (C) may be obtained by extemporaneous mixing of a composition (A) comprising the compound(s) A with a composition (B) comprising the (poly)amine compound(s).Compounds A

[0037] The compound(s) A are chosen from the compounds of formula (I), the optical or geometrical isomers thereof, the solvates thereof, such as hydrates, and mixtures thereof.

[0038] According to a preferred embodiment, the compound(s) A are chosen from the compounds of formula (I), the optical or geometrical isomers thereof, the solvates thereof such as hydrates, and mixtures thereof, such that Z denotes a radical chosen from:a) divalent radicals, preferably C2-C30radicals, optionally interrupted with one or more heteroatoms or groups chosen from -O-, -N(Ra)-, -S-, -C(O)- and / or (hetero)cycle(s), in particular 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 of each other, denote an integer between 1 and 3, preferably 1;b) trivalent radicals, preferably C3-C6, in particular CH2-CH-CH2-; andc) tetravalent radicals, preferably C3-C12, in particular -CH2-C-CH2-CH2-CH2- or -CH2-C-CH2- or the 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.

[0039] According to a preferred embodiment, a (hetero)cycle denotes a heterocyclic divalent radical (i.e. a heterocycle), preferably a heterocycloalkyl radical, more particularly a divalent 3-, 5- or 6-membered heterocycloalkyl radical such as a divalent epoxide radical, a divalent tetrahydrofuran radical or a divalent tetrahydropyran radical, said (hetero)cycle being optionally substituted with one or more radicals chosen from -OR with R as defined previously, and in particular -OH or -O-C(O)-C(Ra)(Rb)-C(O)-R4.

[0040] According to a preferred embodiment, AK2 represents a linear or branched, saturated or unsaturated, C12-C28monovalent hydrocarbon-based chain, optionally substituted with one or more identical or different radicals chosen from -OR, -X-AK3-(O-C(O)-C(Ra)(Rb)-C(O)-R4)v, and / or said chain being optionally interrupted with -O-C(O)- or -C(O)-O-.

[0041] According to a first preferred embodiment variant, the compound(s) A are chosen from the compounds of formula (I), the optical or geometrical isomers thereof, the solvates thereof such as hydrates, and mixtures thereof, 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, saturated or unsaturated, C12-C24monovalent hydrocarbon-based chain, optionally substituted with one or more identical or different radicals chosen from -OR, -X-AK3-(O-C(O)-C(Ra)(Rb)-C(O)-R4)v; and / or said chain being optionally interrupted with one or more heteroatoms or groups chosen from -O-, -S-, -C(O)-, epoxides, and combinations thereof, in particular O-(CO)- or -C(O)-O-;- Y, AK3, v, R, X, R4, Raand Rbbeing as defined previously for formula (I);it being understood that the compounds of formula (I) contain at least two radicals -C(O)-C(Ra)(Rb)-C(O)-R4.

[0042] According to a preferred embodiment, AK2 represents a linear or branched, saturated or unsaturated, C12-C24monovalent hydrocarbon-based chain, optionally substituted with one or more identical or different radicals chosen from -OR, -X-AK3-(O-C(O)-C(Ra)(Rb)-C(O)-R4)v, and / or said chain being optionally interrupted with one or more heteroatoms or groups chosen from -O-, -S-, -C(O)-, and combinations thereof, in particular -O-C(O)- or -C(O)-O-.

[0043] According to this first preferred embodiment variant, the compound(s) A are preferably chosen from compounds (1), (2), (3), (4), (7), (8), (9), (11) and (16) below, the optical or geometrical isomers thereof, the solvates thereof such as hydrates, and mixtures thereof: (1) (2) (3) (4) (7) (8) (9) (11) (16).

[0044] According to this first preferred embodiment variant, the compound(s) A are more preferentially chosen from the compounds (4), the optical or geometrical isomers thereof, the solvates thereof such as hydrates, and mixtures thereof.

[0045] According to a second embodiment variant, the compound(s) A are chosen from the compounds of formula (I), the optical or geometrical isomers thereof, the solvates thereof such as hydrates, and mixtures thereof, such that:- p is equal to 0;- Z represents a linear or branched, saturated or unsaturated, preferably saturated, acyclic, multivalent C4to C24, particularly C6to C20, more particularly C14to C20, in particular C17, hydrocarbon-based radical, Z also being optionally substituted with one or more radicals –[(O)t-(AK1)q- (O-C(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 -(O)t-(AK1)q-(O-C(O)-C(Ra)(Rb)-C(O)-R4)uare identical or different; preferably, n is non-zero;- m is equal to 1;- AK2 represents a linear or branched, saturated or unsaturated, preferably saturated, C3-C8, in particular C4or C6, monovalent hydrocarbon-based chain, substituted with one or more identical or different radicals chosen from -OR, -X-AK3-(O-C(O)-C(Ra)(Rb)-C(O)-R4)v, preferably substituted with one or more radicals -OR; and / or said chain being optionally interrupted with one or more heteroatoms or groups chosen from -O-, -S-, -C(O)-, (hetero)cycle(s), and combinations thereof, in particular -O-C(O)-, -C(O)-O-, -(hetero)cycle-O-(hetero)cycle-, and preferably not being interrupted;- Y, AK1, AK3, t, q, u, v, R, X, R4, Raand Rbbeing as defined previously for formula (I);it being understood that the compounds of formula (I) contain at least two radicals -C(O)-C(Ra)(Rb)-C(O)-R4.

[0046] According to this second embodiment variant, the compound(s) A are preferably chosen from compounds (5) and (6) below, the optical or geometrical isomers thereof, the solvates thereof such as hydrates, and mixtures thereof: (5) (6).

[0047] According to a third embodiment variant, the compound(s) A are chosen from the compounds of formula (I), the optical or geometrical isomers thereof, the solvates thereof such as hydrates, and mixtures thereof, such that:- p is equal to 0;- n + m is equal to 4, m being non-zero;- Z represents an unsubstituted and uninterrupted, linear or branched, saturated or unsaturated, preferably saturated and acyclic, C2to C24, particularly C3to C10, in particular C3, tetravalent hydrocarbon-based radical;- AK2 independently represent a linear or branched, saturated or unsaturated, preferably saturated, C12-C24, preferably C16-C20, in particular C18, monovalent hydrocarbon-based chain, optionally substituted with one or more identical or different radicals chosen from -OR and -X-AK3-(O-C(O)-C(Ra)(Rb)-C(O)-R4)v, preferably substituted with one or more radicals -X-AK3-(O-C(O)-C(Ra)(Rb)-C(O)-R4)v; and / or said chain being optionally interrupted with one or more heteroatoms or groups chosen from -O-, -S-, -C(O)-, (hetero)cycle(s), and combinations thereof, in particular -O-C(O)-, -C(O)-O-, -(hetero)cycle-O-(hetero)cycle-, and preferably not being interrupted;- AK3 represents a linear or branched, saturated or unsaturated C1-C12, preferably C1-C6, more preferentially saturated C1-C6, even more preferentially C2-C4, better still C3, divalent hydrocarbon-based chain;- v is 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, Raand Rbbeing as defined previously for formula (I);it being understood that the compounds of formula (I) contain at least two radicals -C(O)-C(Ra)(Rb)-C(O)-R4.

[0048] According to a preferred embodiment, m is equal to 3, n is equal to 1 and u is equal to 1.

[0049] According to a preferred embodiment, t is equal to 0.

[0050] According to a preferred embodiment, q is equal to 0.

[0051] According to a preferred embodiment, Y denotes -C(O)-O.

[0052] According to a preferred embodiment, none of the radicals AK2 are interrupted.

[0053] According to a preferred embodiment, the radicals AK2 are saturated.

[0054] According to a preferred embodiment, the radicals AK2 are not substituted with -OR.

[0055] According to a preferred embodiment, AK3 represents a divalent linear or branched, saturated or unsaturated C1-C6, more preferentially saturated C1-C6, even more preferentially saturated C1-C4, better saturated C3hydrocarbon-based chain.

[0056] According to this third embodiment variant, the compound(s) A are in particular chosen from the compounds (10) below, the optical or geometrical isomers thereof, the solvates thereof such as hydrates, and mixtures thereof: (10).

[0057] According to a fourth embodiment variant, the compound(s) A are chosen from the compounds of formula (I), the optical or geometrical isomers thereof, the solvates thereof such as hydrates, and mixtures thereof, such that:- p is equal to 1;- Z represents a linear or branched, saturated or unsaturated, preferably saturated and acyclic, multivalent C2to C24, particularly C4to C20, preferably C5or C17, hydrocarbon-based radical, Z also being optionally substituted with one or more radicals –[(O)t-(AK1)q-(O-C(O)-C(Ra)(Rb)-C(O)-R4)u]n, preferably being unsubstituted;- AK2 represents a linear or branched, saturated or unsaturated, preferably saturated, C8-C30, in particular C10-C29, monovalent hydrocarbon-based chain, substituted with one or more identical or different radicals chosen from -OR, -X-AK3-(O-C(O)-C(Ra)(Rb)-C(O)-R4)v, preferably substituted with one or more radicals -OR; and / or said chain being optionally interrupted with one or more heteroatoms or groups chosen from -O-, -S-, -C(O)- and (hetero)cycle(s), and combinations thereof, in particular -O-C(O)-, -C(O)-O- or -(hetero)cycle-O-(hetero)cycle-, and preferably being interrupted with -O-C(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, Raand Rbbeing as defined previously for formula (I);it being understood that the compounds of formula (I) contain at least two radicals -C(O)-C(Ra)(Rb)-C(O)-R4.

[0058] According to a preferred embodiment, n is equal to 0 and m is equal to 1.

[0059] According to a preferred embodiment, Z is a divalent radical.

[0060] According to a preferred embodiment, if Z is an unsaturated chain, AK2 is an unsaturated chain, and if Z is a saturated chain, AK2 is a saturated chain.

[0061] According to this fourth embodiment variant, the compound(s) A are in particular chosen from the compounds (Iic), the optical or geometrical isomers thereof, the solvates thereof such as hydrates, and mixtures thereof:H-Z-Y-AK4-Y’-Z-H (Iic)in which formula (Iic):- Y is as defined previously for formula (I);- Z represents a linear or branched, saturated or unsaturated, preferably saturated, C2to C24, in particular C4to C20, preferably C5or C17, divalent hydrocarbon-based radical;- Y’ represents -C(O)-O- or -O-C(O)- it being understood that if Y represents -O-C(O)-, Y’ represents -C(O)-O-, and if Y represents -C(O)-O-, Y’ represents -O-C(O)-;- AK4 denotes a saturated divalent hydrocarbon-based radical of 5 or 6 carbon atoms, substituted with at least two radicals -OR with R being as defined previously in formula (I);it being understood that the compounds of formula (Iic) contain at least two radicals -C(O)-C(Ra)(Rb)-C(O)-R4, and preferably four radicals -C(O)-C(Ra)(Rb)-C(O)-R4.

[0062] According to this fourth embodiment variant, the compound(s) A are in particular chosen from compounds (12) and (15) below, the optical or geometrical isomers thereof, the solvates thereof such as hydrates, and mixtures thereof: (12) (15).

[0063] According to a fifth embodiment variant, the compound(s) A are chosen from the compounds of formula (I), the optical or geometrical isomers thereof, the solvates thereof such as hydrates, and mixtures thereof, such that:- p is equal to 0;- Z represents a linear or branched, saturated or unsaturated, preferably saturated and acyclic, C2to C24, in particular C3to C10, preferably C4or C5, tetravalent hydrocarbon-based radical, Z also being substituted with one or more radicals –[(O)t-(AK1)q- (O-C(O)-C(Ra)(Rb)-C(O)-R4)u]n, n preferably being equal to 1;- n + m is equal to 4, and preferably m is equal to 3;- AK2 independently represents a linear or branched, saturated or unsaturated, preferably saturated, C14to C30, preferably C16to C24, preferably C17, hydrocarbon-based chain, said chain being optionally substituted with one or more identical or different radicals chosen from -OR, -X-AK3-(O-C(O)-C(Ra)(Rb)-C(O)-R4)v, preferably substituted with one or more radicals -OR; and / or said chain being optionally interrupted with one or more heteroatoms or groups chosen from -O-, -S-, -C(O)-, (hetero)cycle(s), and combinations thereof, in particular -O-C(O)-, -C(O)-O-, -(hetero)cycle-O-(hetero)cycle-, and preferably not being interrupted;- X is as defined previously for formula (I); preferably, X denotes a sulfur atom;- Y, AK1, AK3, u, t, q, v, n, m R, R4, Raand Rbbeing as defined previously for formula (I);it being understood that the compounds of formula (I) contain at least two radicals -C(O)-C(Ra)(Rb)-C(O)-R4.

[0064] According to a preferred embodiment, t is equal to 0 and u is equal to 1.

[0065] According to a preferred embodiment, all the radicals AK2 are identical, and preferably all the radicals Y are identical.

[0066] According to a preferred embodiment, Y denotes -O-C(O)-.

[0067] According to a particular embodiment, the compounds according to this fifth variant are in particular chosen from the compounds (Iid), the optical or geometrical isomers thereof, the solvates thereof such as hydrates, and mixtures thereof:[AK’2-OCO-CH2]3-C-CH2-O-C(O)-C(Ra)(Rb)-C(O)-R4(Iid)in which formula (Iid):- AK’2 represents a linear or branched, preferably linear, saturated or unsaturated, preferably saturated, C14-C30, preferably C16-C24, preferably C17, monovalent hydrocarbon-based chain, said chain being substituted with one or more identical or different radicals chosen from -OR, -S-AK3-(O-C(O)-C(Ra)(Rb)-C(O)-R4)v, preferably substituted with one or more radicals -OR;- AK3, v, R, R4, Raand Rbbeing as defined previously for formula (I);it being understood that said compounds contain at least two radicals -C(O)-C(Ra)(Rb)-C(O)-R4.

[0068] According to a sixth embodiment variant, the compound(s) A are chosen from the compounds of formula (I), the optical or geometrical isomers thereof, the solvates thereof such as hydrates, and mixtures thereof, such that:- p is equal to 0;- m is non-zero;- Z represents a linear or branched, saturated or unsaturated, conjugated or non-conjugated, preferably non-conjugated, acyclic or cyclic, aromatic or non-aromatic, preferably non-aromatic, divalent C2to C24, in particular C3to C12, hydrocarbon-based radical, said radical Z also being interrupted with one or more heteroatoms or groups chosen from -O-, -N(Ra)-, -S-, -C(O)-, 5- or 6-membered heterocycloalkyl(s), and combinations thereof;- AK2 represents a linear or branched, saturated or unsaturated, preferably saturated, C14-C30, preferably C14-C24, preferably C17, monovalent hydrocarbon-based chain, said chain being optionally substituted with one or more identical or different radicals chosen from -OR and -X-AK3-(O-C(O)-C(Ra)(Rb)-C(O)-R4)v, preferably unsubstituted; and / or said chain being optionally interrupted with one or more heteroatoms or groups chosen from -O-, -S-, -C(O)-, (hetero)cycles, and combinations thereof, in particular -O-C(O)-, -C(O)-O- or -(hetero)cycle-O-(hetero)cycle-, preferably optionally interrupted with -O-C(O)- or -C(O)-O-, and more preferentially not being interrupted;- X is as defined previously for formula (I); preferably, X denotes a sulfur atom;- Y, AK1, AK3, v, t, q, u, R, R4, Raand Rbbeing as defined previously for formula (I);it being understood that the compounds of formula (I) contain at least two radicals -C(O)-C(Ra)(Rb)-C(O)-R4.

[0069] According to a preferred embodiment, according to 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 an integer between 1 and 3, preferably 1, (heterocycle) denotes a divalent 5- or 6-membered heterocycloalkyl radical, in particular a divalent tetrahydrofuran radical or a divalent tetrahydropyran radical, said heterocycle being optionally substituted with one or more radicals chosen from -OR, with R as defined previously for formula (I), and notably -OH or -O-C(O)-C(Ra)(Rb)-C(O)-R4.

[0070] According to this sixth embodiment variant, the compound(s) A are in particular chosen from the compounds (Iie), the optical or geometrical isomers thereof, the solvates thereof such as hydrates, and mixtures thereof:AK’’2-C(O)-O-(CH2)g-(heterocycle)-O-(CH2)h-(heterocycle)-(CH2)j-O-CO-AK’’2 (Iie)in which formula (Iie):- h is equal to 0, 1 or 2 and preferably is equal to 0;- g and j independently denote an integer between 1 and 3, preferably 1;- (heterocycle) denotes a divalent 5- or 6-membered heterocycloalkyl radical substituted with one or more identical or different radicals chosen from -OR, with R as defined previously for formula (I), and notably -OH or -O-C(O)-C(Ra)(Rb)-C(O)-R4;- AK’’2 represents a linear or branched, saturated or unsaturated, preferably saturated, C14-C30, preferably C14-C24, preferably C17, monovalent hydrocarbon-based chain, said chain being optionally substituted with one or more identical or different radicals chosen from -OH, -O-C(O)-C(Ra)(Rb)-C(O)-R4and -S-AK3-(O-C(O)-C(Ra)(Rb)-C(O)-R4)v, preferably unsubstituted; and / or said chain being optionally interrupted with one or more heteroatoms or groups chosen from -O-, -S-, -C(O)- and (hetero)cycle(s), and combinations thereof, in particular -O-C(O)-, -C(O)-O- or -(hetero)cycle-O-(hetero)cycle-, preferably optionally interrupted with -O-C(O)- or -C(O)-O-, and more preferentially not being interrupted;it being understood that the compounds of formula (Iie) contain at least two radicals -C(O)-C(Ra)(Rb)-C(O)-R4.

[0071] According to this sixth embodiment variant, the compound(s) A are in particular chosen from the compounds (14) below, the optical or geometrical isomers thereof, the solvates thereof such as hydrates, and mixtures thereof: (14)with W being a hydrogen atom or -C(O)-C(Ra)(Rb)-C(O)-R4, and said compound containing at least two groups -C(O)-C(Ra)(Rb)-C(O)-R4.

[0072] Preferably, the compound(s) A are chosen from the compounds of formula (Ia), the optical or geometrical isomers thereof, the solvates thereof such as hydrates, and mixtures thereof:Z-(Y-AK2)3(Ia)in which formula (Ia):- Z represents -CH2-CH-CH2-;- AK2 independently denotes a linear or branched, saturated or unsaturated, C12-C24monovalent hydrocarbon-based chain, optionally substituted with one or more identical or different radicals chosen from -OR and -X-AK3-(O-C(O)-C(Ra)(Rb)-C(O)-R4)v; and / or said chain being optionally interrupted with one or more heteroatoms or groups chosen from -O-, -S-, -C(O)-, epoxides, and combinations thereof, in particular O-C(O)- and -C(O)-O-;- Y, AK3, v, R, X, R4, Raand Rbbeing as defined previously for formula (I); preferably, Y denotes -O-C(O);it being understood that the compounds of formula (Ia) contain at least two radicals -C(O)-C(Ra)(Rb)-C(O)-R4.

[0073] Preferably, the compound(s) A are chosen from the compounds of formula (Ib), the optical or geometrical isomers thereof, the solvates thereof such as hydrates, and mixtures thereof:m(AK2 -Y) – Z – [(O)t-(AK1)q-(O-C(O)-C(Ra)(Rb)-C(O)-R4)u]n(Ib)in which formula (Ib):- n + m is equal to 4, m being non-zero; m and n being as defined previously for formula (I);- Z represents an unsubstituted and uninterrupted, linear or branched, saturated or unsaturated, preferably saturated and acyclic, C2to C24, in particular C3to C10preferably C3, tetravalent hydrocarbon-based radical;- AK2 independently represent a linear or branched, saturated or unsaturated, preferably saturated, C12-C24, preferably C16-C20, preferably C18, monovalent hydrocarbon-based chain, optionally substituted with one or more identical or different radicals chosen from -OR and -X-AK3-(O-C(O)-C(Ra)(Rb)-C(O)-R4)v, preferably substituted with one or more radicals -X-AK3-(O-C(O)-C(Ra)(Rb)-C(O)-R4)v; and / or said chain being optionally interrupted with one or more heteroatoms or groups chosen from -O-, -S-, -C(O)-, (hetero)cycle(s), and combinations thereof, in particular -O-C(O)-, -C(O)-O- or -(hetero)cycle-O-(hetero)cycle-, and preferably not being interrupted;- AK3 represents a linear or branched, saturated or unsaturated C1-C12, preferably C1-C6, more preferentially saturated C1-C6, even more preferentially C2-C4, preferably C3, divalent hydrocarbon-based chain;- v is 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, t, q, u, R, R4, Raand Rbbeing as defined previously for formula (I);it being understood that the compounds of formula (Ib) contain at least two radicals -C(O)-C(Ra)(Rb)-C(O)-R4.

[0074] Preferably, the compound(s) A are chosen from the compounds of formula (Ic), the optical or geometrical isomers thereof, the solvates thereof such as hydrates, and mixtures thereof:m(AK2-Y) – ZH – [(O)t-(AK1)q-(O-C(O)-C(Ra)(Rb)-C(O)-R4)u]n(Ic)in which formula (Ic):- Z represents a linear or branched, saturated or unsaturated, preferably saturated and acyclic, multivalent C14to C24, particularly C16to C20, such as C17, hydrocarbon-based radical, Z also being optionally substituted with one or more radicals –[(O)t-(AK1)q- (O-C(O)-C(Ra)(Rb)-C(O)-R4)u]n, preferably unsubstituted;- AK2 represents a linear or branched, saturated or unsaturated, preferably saturated, C14-C30, preferably C20-C29, monovalent hydrocarbon-based chain, substituted with one or more identical or different radicals chosen from -OR and -X-AK3-(O-C(O)-C(Ra)(Rb)-C(O)-R4)v, preferably substituted with one or more radicals -OR; and / or said chain being optionally interrupted with one or more heteroatoms or groups chosen from -O-, -S-, -C(O)-, (hetero)cycle(s), and combinations thereof, in particular -O-C(O)-, -C(O)-O-, -(hetero)cycle-O-(hetero)cycle-, and preferably interrupted with -O-C(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, Raand Rbbeing as defined previously for formula (I);it being understood that the compounds of formula (Ic) contain at least two radicals -C(O)-C(Ra)(Rb)-C(O)-R4.

[0075] Preferably, the compound(s) A are chosen from the compounds of formula (Id), the optical or geometrical isomers thereof, the solvates thereof such as hydrates, and mixtures thereof:m(AK2-Y) – Z – [(O)t-(AK1)q-(O-C(O)-C(Ra)(Rb)-C(O)-R4)u]n(Id)in which formula (Id):- n + m is equal to 4, and preferably m is equal to 3;- Z represents a linear or branched, saturated or unsaturated, preferably saturated or acyclic, C2to C24, in particular C3to C10, in particular C4or C5, tetravalent hydrocarbon-based radical, Z also being substituted with one or more radicals –[(O)t-(AK1)q- (O-C(O)-C(Ra)(Rb)-C(O)-R4)u]n, n preferably being equal to 1;- AK2 independently represents a linear or branched, saturated or unsaturated, preferably saturated, C14-C30, preferably C16-C24, preferably C17, monovalent hydrocarbon-based chain, said chain being optionally substituted with one or more identical or different radicals chosen from -OR and -X-AK3-(O-C(O)-C(Ra)(Rb)-C(O)-R4)v, preferably substituted with one or more radicals -OR; and / or said chain being optionally interrupted with one or more heteroatoms or groups chosen from -O-, -S-, -C(O)- and (hetero)cycle(s), and combinations thereof, in particular -O-C(O)-, -C(O)-O- or (hetero)cycle-O-(hetero)cycle, and preferably not being interrupted; X is as defined previously for formula (I) and preferably X denotes a sulfur atom; Y, AK1, AK3, v, R, R4, Raand Rbbeing as defined previously for formula (I),it being understood that the compounds of formula (Id) contain at least two radicals -C(O)-C(Ra)(Rb)-C(O)-R4.

[0076] Preferably, the compound(s) A are chosen from the compounds of formula (Ie), the optical or geometrical isomers thereof, the solvates thereof such as hydrates, and mixtures thereof:m(AK2-Y) – Z – [(O)t-(AK1)q-(O-C(O)-C(Ra)(Rb)-C(O)-R4)u]n(Ie)in which formula (Ie):- n + m is equal to 2, m being non-zero, and m preferably being equal to 2; n is as defined in Claim 1; preferably, n is zero;- Z represents a linear or branched, saturated or unsaturated, conjugated or non-conjugated, preferably non-conjugated, acyclic or cyclic, aromatic or non-conjugated, preferably non-aromatic, C2to C24, in particular C3to C12, divalent hydrocarbon-based radical, said radical Z also being interrupted with one or more heteroatoms or groups chosen from -O-, -N(Ra)-, -S-, -C(O)-, (hetero)cycle(s), and combinations thereof; 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 divalent heterocyclic radical (i. e. a heterocycle), preferably a heterocycloalkyl radical, more particularly a divalent 5- or 6-membered heterocycloalkyl radical, in particular a divalent tetrahydrofuran radical or a divalent tetrahydropyran radical, said heterocycle being optionally substituted with one or more radicals chosen from -OR with R as defined in Claim 1, and notably -OH or -O-C(O)-C(Ra)(Rb)-C(O)-R4;- AK2 represents a linear or branched, saturated or unsaturated, preferably saturated, C14-C30, preferably C14-C24, preferably C17, monovalent hydrocarbon-based chain, said chain being optionally substituted with one or more identical or different radicals chosen from -OR and -X-AK3-(O-C(O)-C(Ra)(Rb)-C(O)-R4)v, preferably unsubstituted; and / or said chain being optionally interrupted with one or more heteroatoms or groups chosen from -O-, -S-, -C(O)-, (hetero)cycles, and combinations thereof, in particular -O-C(O)-, -C(O)-O- or -(hetero)cycle-O-(hetero)cycle-, preferably optionally interrupted with -O-C(O)- or -C(O)-O-, and more preferentially not being interrupted;- X is as defined previously for formula (I); preferably, X denotes a sulfur atom;- Y, AK1, AK3, v, t, q, u, R, R4, Raand Rbbeing as defined previously for formula (I);it being understood that the compounds of formula (Ie) contain at least two radicals -C(O)-C(Ra)(Rb)-C(O)-R4.

[0077] According to a preferred embodiment, the compound(s) A are chosen from the following compounds (1) to (16), the optical or geometrical isomers thereof, the solvates thereof such as hydrates, and mixtures thereof: (1) (2) (3) (4) (5) (6) (7) (8) (9) (10) (11) (12) (13) (14) (15) (16)with W being a hydrogen atom or -C(O)-C(Ra)(Rb)-C(O)-R4, and said compound containing at least two groups -C(O)-C(Ra)(Rb)-C(O)-R4.Preparation of the compounds of formula (I)

[0078] In particular, the compound(s) of formula (I), or (Ia), (Ib), (Ic), (Id), (Ie), (Iic), (Iid) or (Iie), may be prepared via the following sequence of reactions:First step

[0079] In a first step, a commercial polyol, which is preferably natural, of formula (H)p-Z(OH)m’, is reacted with m equivalents of fatty derivatives R’CO-AK’2with 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)p-Z(OH)m’+mR’CO-AK’2-> (H)p-Z(OH)m’-m(YAK’2)min which scheme:- Y represents -O-C(O)-;- R’ denoting in particular -OH or -Cl; preferably, R’ denotes -OH;- AK’2 represents a linear or branched, unsaturated, C1-C40, preferably C14-C20, hydrocarbon-based chain, said chain being optionally interrupted with one or more heteroatoms or groups chosen from -O-, -S-, -C(O)-, (hetero)cycle(s), and combinations thereof, in particular -O-C(O)-, -C(O)-O- or -(hetero)cycle-O-(hetero)cycle-, preferably interrupted with -O- or -S-, more preferentially not being interrupted.

[0080] According to a preferred embodiment, m is equal to m’.

[0081] The polyols (H)p-Z(OH)m’may be cyclic or acyclic.

[0082] By way of example of cyclic polyols (H)p-Z(OH)m’, mention may be made of maltose, lactose, raffinose, sucrose, trehalose, melibiulose, melibiose, mannobiose, kojibiose, nigerose, isomaltose, rutinose, rutinulose, xylobiose or sorbitan.

[0083] As examples of acyclic polyols (H)p-Z(OH)m’, mention may be made of ethylene glycol, propylene glycol, butylene glycol, pentylene glycol, hexylene glycol, butanediol, glycerol, pentaerythritol, dipentaerythritol, trimethylolethane, mannitol or trimethylolpropane.

[0084] According to a preferred embodiment, the polyol (H)p-Z(OH)m’is chosen from glycerol, mannitol, sucrose, ethylene glycol, sorbitan or trimethylolpropane, and more preferentially the polyol (H)p-Z(OH)m’denotes glycerol.

[0085] The compounds R’CO-AK’2are preferably unsaturated fatty acids containing from 15 to 36 carbon atoms, preferably from 15 to 24 carbon atoms. They may be mono- or polyunsaturated.

[0086] The monounsaturated fatty acids are in particular chosen from palmitoleic acid, oleic acid, 9-eicosenoic acid, 11-eicosenoic acid, erucic acid and nervonic acid.

[0087] The polyunsaturated fatty acids are notably chosen from linoleic acid, α-linolenic acid, γ-linolenic acid, dihomo-γ-linolenic acid, arachidonic acid, eicosapentaenoic acid, docosahexaenoic acid, ruminic acid and hydroxyl monounsaturated fatty acids notably chosen 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 hydroxyl fatty acids notably chosen from densipolic acid, auricolic acid, dimorphecolic acid.

[0088] More preferentially, the unsaturated fatty acid is chosen from ricinoleic acid, oleic acid, palmitoleic acid, erucic acid and mixtures thereof.Second step

[0089] In a second step, all or some of the unsaturation(s) of the radical(s) AK’2 are converted a) via an epoxidation reaction into epoxide to yield the derivatives (III), such as the starting compound a1 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 yield the derivatives (IV), for instance compound b3 illustrated in the scheme described below.

[0090] The thiol-ene reaction b) may be performed using (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 preferably including from 1 to 6 carbon atoms, such as 3-mercapto-3-methylbutanol, 3-mercapto-2-butanol, or such as polyhydroxylated thiols, preferably including from 1 to 6 carbon atoms, such as 3-mercapto-1,2-propanediol HS-CH(OH)-CH2OH.

[0091] The compounds (IV) obtained are thus substituted with a radical -S-AK3-(OH)vwith 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 as defined previously for the compounds of formula (I).Third step

[0092] In a third step, all or some of the epoxide groups of the compounds of formula (III) are opened with nucleophilic compounds, in particular i) alcohols preferably of C1-C4such as methanol or ethanol, or even a polyol to give compounds (IIIi), such as compound b2 illustrated in the scheme hereinbelow, ii) carboxylic acids, preferably of C1-C6, such as lactic acid, pyruvic acid, benzoic acid, glycolic acid or 2,2-bishydroxymethylpropionic acid, more preferentially carboxylic acids substituted with at least one hydroxyl radical such as lactic acid, to yield the compounds (IIIii), such as compound b1 illustrated in the scheme hereinbelow.

[0093] According to a preferred embodiment, the carboxylic acid ii) is chosen from lactic acid, glycolic acid or 2,2-bishydroxymethylpropionic acid (epoxy-acid reaction) and the reaction is performed in the presence of a catalyst such as imidazole, 1-methylimidazole, N,N-dimethylbenzylamine or caffeine.

[0094] According to a preferred embodiment, the alcohol i) is chosen from ethylene glycol, propylene glycol, butylene glycol, pentylene glycol, hexylene glycol, butanediol, glycerol, pentaerythritol, dipentaerythritol, trimethylolethane and trimethylolpropane, more preferentially butylene glycol or trimethylolethane.Fourth step

[0095] In a fourth step, all or some of the alcohol functions -OH of the compounds (IIIi) or (IIIii) and all or some of the alcohol functions which may possibly still be present originating from the polyols (H)p-Z(OH)m’used in the first step are converted into radicals -O-C(O)-C(Ra)(Rb)-C(O)-R4, for example via a (trans)esterification reaction with an ester Gp-C(O)-C(Ra)(Rb)-C(O)-R4, in which Gp preferably denotes a hydroxyl radical or a (C1-C4)alkoxy radical, such as methoxy, ethoxy, isobutoxy or t-butoxy.

[0096] According to a preferred embodiment, Gp-C(O)-C(Ra)(Rb)-C(O)-R4denotes an ester chosen from ethyl acetoacetate, ethyl 2-methylacetoacetate and tert-butyl acetoacetate, preferably tert-butyl acetoacetate.

[0097] The compounds of structures (Ia), (Ic), such as the compounds of structure (Iic), and the compounds of structures (Id) and (Ie) may be obtained according to this process.

[0098] By way of example, step 4 may be performed according to the protocol described in Trevino, A.S., and Trumbo, D.L. (2002). Acetoacetylated castor oil in coating applications. Progress in Organic Coatings, 44(1), 49-54:

[0099] In certain cases, the compounds (H)p-Z(OH)m’-m(YAK’2)mresulting from the first step are commercial; in particular, certain compounds for which m’ is equal to m, p is equal to 0, Z preferably denoting -CH2-CH-CH2-, are commercial. When p is equal to 0 and m’ is equal to m, the compounds are esters of optionally hydroxylated unsaturated fatty acids, in particular triglycerides of castor oil, soybean oil, canola oil or linseed oil. The synthesis of compounds (Ia) to (Ie) then begins from the second step described above.

[0100] For example, starting with an unsaturated triglyceride, a thiol-ene reaction is performed with a (poly)hydroxyl thiol such as SH-(CH2)xOH with x being an integer preferably from 1 to 4, and then a transesterification reaction (as described in Desroches, M., Caillol, S., Lapinte, V., Auvergne, R. and Boutevin, B. (2011). Synthesis of biobased polyols by thiol-ene coupling from vegetable oils. Macromolecules, 44(8), 2489–2500:

[0101] For example, starting with an unsaturated triglyceride, a total or partial epoxidation reaction is performed, followed by opening of the epoxide(s) formed, which generates alcohol functions and (trans)esterification. A commercial epoxidized triglyceride, such as the products sold by Arkema under the trade names Vikoflex 7170 or Vikoflex 7190, may also be used as starting material.

[0102] By way of example, the reaction scheme below may be used, in which all the epoxides are opened with lactic acid and each hydroxyl is then esterified with t-Bu-OCOCH2CH3, according to the scheme below:

[0103] By way of example, the reaction scheme below may also be used, in which all the epoxides are opened with an alcohol, methanol in the example, and each hydroxyl is then esterified with t-Bu-OCOCH2CH3:

[0104] The compounds of formulae (Ia) to (Ie) may also be prepared via the following sequence of reactions:- In a first step, a preferably natural commercial polyacid (H)p-Z(COOH)m’is reacted 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)p-Z(COOH)m’+mHO-AK’2 -> (H)p-Z(COOH)m’-m(YAK’2)min which Y denotes -C(O)-O-, and AK’2 represents a monovalent linear or branched, unsaturated, C1-C40, preferably C14-C20, hydrocarbon-based chain, said chain optionally being interrupted with one or more heteroatoms or groups chosen from -O-, -S-, -C(O)-, (hetero)cycle(s), and combinations thereof, in particular -O-C(O)-, -C(O)-O-, -(hetero)cycle-O-(hetero)cycle-, preferably interrupted with -O- or -S-, and more preferentially not being interrupted.

[0105] According to a preferred embodiment, m is equal to m’.

[0106] The polyacids (H)p-Z(COOH)m’may be cyclic or acyclic.

[0107] The polyacids may preferably denote optionally hydroxylated dicarboxylic acids, optionally hydroxylated tricarboxylic acids, or optionally hydroxylated tetracarboxylic acids.

[0108] The non-hydroxylated dicarboxylic acids are notably chosen 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, glutaric acid, adipic acid, fumaric acid and itaconic acid, and preferably propanedioic acid, butanedioic acid and pentanedioic acid.

[0109] The hydroxylated dicarboxylic acids are notably chosen from tartaric acid, malic acid, aleuritic acid, 7,18-dihydroxytetracos-15-enoic acid and avenic acid B, and preferably malic acid and tartaric acid.

[0110] The (hydroxy)tricarboxylic acids are notably chosen from 2-oxaloglutaric acid, oxalosuccinic acid, 3-carboxymethylmuconic acid, 2-methylcitric 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 and agaric acid, preferably citric acid and aconitic acid.

[0111] The tetracarboxylic acids are notably chosen from 1,2,3,4-butanetetracarboxylic acid, pyromellitic acid, oxydisuccinic acid, thiodisuccinic acid, N-[1,2-dicarboxyethyl]-L-aspartic acid, ethylenediaminetetraacetic acid, ethylenediaminetetrapropionic acid and N,N’-ethylenebis(L-aspartic acid).

[0112] According to a preferred embodiment, the fatty alcohols HO-AK’2 are chosen from fatty alcohols comprising from 15 to 36 carbon atoms, preferably from 15 to 24 carbon atoms.

[0113] The fatty alcohols HO-AK’2 may be mono- or polyunsaturated (presence of one or more ethylenic double bonds).

[0114] The fatty alcohols HO-AK’2 may contain several alcohol functions.

[0115] The monounsaturated fatty alcohols are notably chosen from oleyl alcohol, docosenol, or unsaturated fatty alcohol ethers, such as polyoxyethylene monooleyl ether, preferably oleyl alcohol. The unsaturated monounsaturated fatty alcohols containing several alcohol functions are notably chosen from 9-octadecene-1,12-diol.

[0116] The polyunsaturated fatty alcohols are notably chosen from linoleic alcohol, 2,4-dodecadien-1-ol and dolichols (with n being greater than or equal to 3 and less than or equal to 5).

[0117] According to a preferred embodiment, the fatty alcohol HO-AK’2 is chosen from oleyl alcohol, linoleyl alcohol or mixtures thereof.

[0118] The following steps are identical to those described previously:

[0119] - In a second step, all or some of the unsaturation(s) of the radical(s) AK’2 are converted a) via an epoxidation reaction into epoxide to yield derivatives (III'), 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 yield derivatives (IV’), such as compound b5 illustrated in the scheme below.

[0120] - In a third step, all or some of the epoxide groups of the compounds of formula (III’) are opened with nucleophilic compounds, such as i) preferably C1-C4alcohols such as methanol or ethanol or even a polyol to yield compounds (III’i), such as compound b4 illustrated in the scheme below, ii) carboxylic acids preferably of C1-C6, such as lactic acid, pyruvic acid or benzoic acid, more preferentially carboxylic acids substituted with at least one hydroxyl radical, such as lactic acid, to yield compounds (III’ii), such as compound b6 illustrated in the scheme below.

[0121] - In a fourth step, all or some of the alcohol functions -OH of the compounds (III’i) or (III’ii) and all or some of the alcohol functions which may still be present and which are derived from the polyols (H)p-Z(OH)m’used in the first step are converted into radicals -O-C(O)-C(Ra)(Rb)-C(O)-R4, for example via a transesterification reaction with an ester Gp-C(O)-C(Ra)(Rb)-C(O)-R4in which Gp preferably denotes a hindered alkoxy radical such as tBu-O-, to give the corresponding compounds of formula (I).

[0122] The compounds of formulae (Ia) to (Ie) such that p is equal to 1, Y denotes -C(O)-O- and m is equal to 1 may also be prepared by combining steps 2, 3 and 4 described previously, 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.

[0123] By way of example, the reaction scheme below may be used, in which all the epoxides are opened with methanol and each hydroxyl is then esterified with t-Bu-OCOCH2CH3:

[0124] By way of example, the reaction scheme below may be used, in which an unsaturated oil reacts with a (poly)hydroxyl 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. and Boutevin, B. (2011). Synthesis of biobased polyols by thiol-ene coupling from vegetable oils. Macromolecules, 44(8), 2489–2500):

[0125] By way of example, the reaction scheme below may be used, in which all the epoxides are opened with lactic acid and each hydroxyl is then esterified with t-Bu-OCOCH2CH3: (Poly)amine compounds

[0126] The (poly)amine compound(s) may be chosen in particular from polyamine compounds bearing several primary and / or secondary amine groups or from amino alkoxysilanes, and more particularly from amino alkoxysilane compounds, diamine compounds, triamine compounds, and mixtures thereof.

[0127] The (poly)amine compound(s) may be chosen from compounds comprising from 2 to 20 carbon atoms, notably non-polymeric compounds; they may be acyclic or cyclic, linear or branched, saturated or unsaturated, conjugated or non-conjugated, aromatic or non-aromatic, optionally interrupted with one or more heteroatoms or groups chosen from -O-, -S-, -Si(R’)2- and -N(R’’)-, preferably -O-, -Si(R’)2-, or combinations thereof such as -Si(R’)2-O- or -O-Si(R’)2-, with R’, which may be identical or different, representing a (C1-C4)alkyl group such as methyl, and R’’ representing a hydrogen atom or a (C1-C4)alkyl group, preferably a hydrogen atom.

[0128] The term “non-polymeric compound” means a compound which is not directly obtained via a monomer polymerization reaction.

[0129] (Poly)amine compounds that may be mentioned in particular include N-methyl-1,3-diaminopropane, N-propyl-1,3-diaminopropane, N-isopropyl-1,3-diaminopropane, N-cyclohexyl-1,3-diaminopropane, 2-(3-aminopropylamino)ethanol, 3-(2-aminoethyl)aminopropylamine, bis(3-aminopropyl)amine, methylbis(3-aminopropyl)amine, N-(3-aminopropyl)-1,4-diaminobutane, N,N-dimethyldipropylenetriamine, 1,2-bis(3-aminopropylamino)ethane, N,N’-bis(3-aminopropyl)-1,3-propanediamine, ethylenediamine, 1,3-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-1,13-tridecanediamine, spermidine and C36-alkylenediamines (PriamineTM1071, 1073, 1074, 1075, respectively), preferably spermidine and / or 4,7,10-trioxa-1,13-tridecanediamine.

[0130] According to a particular embodiment of the invention, the (poly)amine compound(s) are monoamine compounds, i.e. they contain only one primary and / or secondary amine group, preferably a primary amine group (NH2).

[0131] The (poly)amine compound(s) may be chosen from amino alkoxysilanes, notably of formula R’1Si(OR’2)z(R’3)xin which:- R’1is a linear or branched, saturated or unsaturated, cyclic or acyclic C1-C6hydrocarbon-based chain substituted with a group chosen from primary amine groups NH2or secondary amine groups -N(H)R with R representing a C1-C4alkyl, an aryl or a benzyl substituted with an amino group or with a C1-C4aminoalkyl group; R’1may be interrupted in its chain with a heteroatom (O, S, NH) or a carbonyl group (CO), R’1being linked to the silicon atom directly via a carbon atom,- R’2and R’3, which may be identical or different, represent a linear or branched (C1-C6)alkyl group,- z denotes an integer ranging from 1 to 3, and- x denotes an integer ranging from 0 to 2,with z + x = 3.

[0132] In particular, R’1is an acyclic chain. Preferably, R’1is a linear or branched, saturated or unsaturated C1-C6hydrocarbon-based chain substituted with an amine -NH2or -N(H)R group, with R representing a C1-C6alkyl, a C3-C6cycloalkyl or a C6aromatic group. More preferentially, R’1is a saturated linear C1-C6hydrocarbon-based chain substituted with an amine group NH2. Even more preferentially, R’1is a saturated linear C2-C4hydrocarbon-based chain substituted with an amine group NH2.

[0133] In particular, R’2represents an alkyl group comprising from 1 to 4 carbon atoms; preferably, R’2represents a linear alkyl group comprising from 1 to 4 carbon atoms and more preferentially R’2represents an ethyl group.

[0134] In particular, R’3represents an alkyl group comprising from 1 to 4 carbon atoms; preferably, R’3represents a linear alkyl group comprising from 1 to 4 carbon atoms and more preferentially R’3represents methyl or ethyl groups. Preferably, z is equal to 3.

[0135] In particular, the (poly)amine compound(s) are chosen from amino alkoxysilanes including only one primary and / or secondary, preferably primary (NH2), amine group, such as 3-aminopropyltriethoxysilane (APTES), 3-aminoethyltriethoxysilane (AETES), 3-aminopropylmethyldiethoxysilane, N-(2-aminoethyl)-3-aminopropyltriethoxysilane, 3-(m-aminophenoxy)propyltrimethoxysilane, p-aminophenyltrimethoxysilane, and N-(2-aminoethylaminomethyl)phenethyltrimethoxysilane.

[0136] Preferably, the (poly)amine compound(s) are chosen from 3-aminopropyltriethoxysilane (APTES), 3-aminoethyltriethoxysilane (AETES), 3-aminopropylmethyldiethoxysilane, and N-(2-aminoethyl)-3-aminopropyltriethoxysilane, and more preferentially 3-aminopropyltriethoxysilane (APTES), in particular the product sold by Sigma Aldrich.

[0137] The (poly)amine compounds may also be chosen from amino polymers, notably having a weight-average molecular weight ranging from 500 g.mol-1to 1 000 000 g.mol-1, preferably ranging from 500 g.mol-1to 500 000 g.mol-1, and preferentially ranging from 500 g.mol-1to 100 000 g.mol-1.

[0138] According to a particular embodiment of the invention, the (poly)amine compounds are monoamine compounds and are chosen from polydialkylsiloxanes notably 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)in which formula (IV):- Alk represents a (C1-C4) alkylene group which is linear or branched, preferably linear, such as propylene,- R’2and R’3, which may be identical or different, preferably identical, represent a (C1-C4)alkyl group, such as methyl, and- R’4represents a linear or branched (C1-C6)alkyl group, preferably C4, such as n-butyl, n represents an integer greater than or equal to 2, preferably the value of n is such that the weight-average molecular weight of the polydimethylsiloxane ranges from 500 to 3000 g.mol-1. As examples of polydimethylsiloxanes (V), mention may be made of the products sold under the names MCR-A11 and MCR-A12 by the company Gelest.

[0139] According to a particular embodiment of the invention, the (poly)amine compounds are diamine compounds, i.e. they contain two primary and / or secondary amine groups, preferably primary amine groups (NH2).

[0140] More particularly, they are chosen from the compounds of formula (V) or (VI):▪ ALK[(O-ALK’)m-NH2]2(V)or▪ H2N-ALK-Si(R’)2-[O-Si(R’)2]m-O-Si(R)2-ALK’-NH2(VI)in which formulae (V) and (VI):- ALK and ALK’, which may be identical or different, represent a linear or branched (C1-C6)alkylene group, preferably a linear group such as propylene,- R’, which may be identical or different, represents a (C1-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 weight-average molecular weight of compound (V) or (VI) ranges from 500 g.mol-1to 55 000 g.mol-1.

[0141] As examples of compounds of formula (VI), mention may be made of those sold under the names DMS-A11, DMS-A12, DMS-A15, DMS-A21, DMS-A31, DMS-A32 and DMS-A35 by the company Gelest.

[0142] The (poly)amines compounds that are diamines are particularly polyether diamines notably of formula H2N-ALK-O-[ALK’-O]m-ALK’’-NH2with ALK, ALK’ and ALK’’, which may be identical or different, representing a linear or branched (C1-C6))alkylene group, and m representing an integer greater than or equal to 0, such as 4,7,10-trioxa-1,13-tridecanediamine or the compounds known under the reference Jeffamine from the company Hunstman, and more particularly α,ω-diamino polyethylene glycol and / or polypropylene glycol (with an amine function at the end of the chain) such as the products sold under the names Jeffamine D-230, D-400, D-2000, D-4000, ED-600, ED-9000 and ED-2003.

[0143] According to a particular embodiment of the invention, the (poly)amine compound(s) are triamine compounds, i.e. they contain three primary and / or secondary amine groups, preferably primary amine groups (NH2). More particularly, they are chosen from polyether triamines notably of formula ALK’’’[(O-ALK’)m-NH2]3with ALK’ as defined previously and ALK’’’ representing a linear or branched trivalent (C1-C6)alkylene group, and m representing an integer greater than or equal to 0.

[0144] As (poly)amine compounds which are triamine compounds, triamine polyethers are mentioned in particular, such as those sold under the name Jeffamine T-403.

[0145] According to another particular embodiment of the invention, the (poly)amine compound(s) include more than three primary and / or secondary amine groups, preferably primary amine groups (NH2).

[0146] In this variant, the (poly)amine compound(s) are chosen in particular from poly(meth)acrylates or poly(meth)acrylamides bearing primary or secondary amine side functions, such as poly(3-aminopropyl)methacrylamide and poly(2-aminoethyl) methacrylate.

[0147] Preferably, the (poly)amine compounds are chosen from chitosans (notably poly(D-glucosamine)) and polydimethylsiloxanes comprising primary amine groups at the end of the chain and / or on side chains.

[0148] According to this variant, the (poly)amine compound(s) are chosen in particular from poly((C2-C5)alkyleneimines), and preferably polyethylenimines and polypropyleneimines, notably poly(ethyleneimine), in particular the product sold under reference 408700 by the company Aldrich Chemical or under the trade name Lupasol by BASF, notably with a molecular weight of between 1200 and 25 000; poly(allylamine), in particular the product sold under reference 479136 by the company Aldrich Chemical; polyvinylamines and copolymers thereof, notably with vinylamides, in particular vinylamine / vinylformamide copolymers such as those sold under the name Lupamin®9030 by the company BASF; polyamine acids containing NH2groups, such as polylysine, in particular the product sold by the company JNC Corporation (formerly Chisso); amino dextran, in particular the product sold by the company CarboMer Inc; amino polyvinyl alcohol, in particular the product sold by the company CarboMer Inc; acrylamido(C1-C6)alkylamine-based copolymers, notably acrylamidopropylamine-based copolymers; and poly(D-glucosamine), for example sold under the reference Kionutrime CSG®by the company Kytozyme.

[0149] According to a particular embodiment, the polydimethylsiloxanes comprising primary amine groups at the end of the chain and / or on side chains are chosen from the compounds of formula (VII) below:Ra-Si(Rb)(Rc)-O-[Si(Rb)(Rc)-O]m-[Si(ALK1-NH2)(Ra)-O]n-Si(Rb)(Rc)-Ra(VII)in which formula (VII):- Ra, which may be identical or different, represents a hydroxyl or (C1-C4)alkyl group,- Rband Rc, which may be identical or different, preferably identical, represent a (C1-C4)alkyl group, such as methyl,- ALK1represents a linear or branched (C1-C6) alkylene group, optionally interrupted with an N(H) group,- m and n are integers greater than or equal to 1; preferably, m and n are such that the weight-average molecular mass of the compound of formula (VII) ranges from 1000 g.mol-1to 500 000 g.mol-1.

[0150] According to a preferred variant, formula (VII) is such that Ra, Rband Rcrepresent a methyl group, ALK1represents a propylene group, n and m are such that the weight-average molecular weight of the polydimethylsiloxane ranges from 1000 g.mol-1to 55 000 g.mol-1.

[0151] As examples of polydimethylsiloxanes of formula (VII), mention may be made of those sold under the names AMS-132, AMS-152, AMS-162, AMS-163, AMS-191 and AMS-1203 by the company Gelest.

[0152] According to another variant, formula (VII) is such that Rarepresents a hydroxyl or (C1-C4)alkyl group, such as methyl, ALK1represents a (C5-C6)alkylene group substituted with an NH group; preferably, ALK1represents -(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.mol-1to 500 000 g.mol-1.

[0153] As amine polymer, mention may also be made of α,ω-diamino polytetrahydrofurans (or polytetramethylene glycol) and α,ω-diamino polybutadienes.

[0154] According to a particular embodiment of the invention, the (poly)amine compounds are chosen 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.

[0155] According to a preferred embodiment, the (poly)amine compound(s) are chosen from:ia) (poly)amine compounds including more than three primary and / or secondary amine groups, preferably primary (NH2), in particular chitosans such as poly(D-glucosamine) and polylysine,ib) polyether diamines, in particular polyethylene glycol α,ω-diamines, bearing a chain-end amine function,ic) polyether triamines such as Jeffamine T-403,id) aminoalkoxysilanes, in particular APTES,ie) polyamine compounds NH2-alk-NH2, in which alk denotes a divalent C2-C20hydrocarbon-based chain, optionally interrupted with one or more heteroatoms chosen from -O-, -N(R)- with R denoting a hydrogen atom or a C1-C4alkyl radical, notably spermidine and 4,7,10-trioxa-1,13-tridecanediamine, andif) polydialkylsiloxanes comprising primary amine groups at the end of the chain or on side chains, in particular polydimethylsiloxanes comprising primary amine groups, more particularly bis(3-aminopropyl)-terminated poly(dimethoxysiloxane) (PDMS-diNH2) and amodimethicones comprising amine groups on side chains, even more particularly bis-cetearyl amodimethicone.

[0156] According to a more preferred embodiment, the (poly)amine compound(s) are chosen from ic) polyether triamines, such as Jeffamine T-403.Compositions (B) and (C)

[0157] Composition (C) preferably comprises a total content of compounds A ranging from 0.005% to 5% by weight, more preferentially ranging from 0.1% to 3% by weight, even more preferentially ranging from 0.1% to 2% by weight, relative to the total weight of composition (C).

[0158] When composition (C) also comprises one or more (poly)amine compounds, composition (C) preferably comprises a total content of (poly)amine compounds ranging from 0.005% to 5% by weight, more preferentially ranging from 0.1% to 3% by weight, even more preferentially ranging from 0.1% to 2% by weight, relative to the total weight of composition (C).

[0159] Composition (C) is a cosmetic composition, i.e. a composition which comprises a cosmetically acceptable medium, i.e. a medium that is compatible with human keratin fibers.

[0160] When it is present, composition (B) is a cosmetic composition, i.e. a composition which comprises a cosmetically acceptable medium, i.e. a medium that is compatible with human keratin fibers.

[0161] According to a preferred embodiment, composition (B) and / or (C) comprises one or more polar and / or protic solvents, preferably chosen from monoalcohols containing from 2 to 6 carbon atoms, more preferentially chosen from ethanol, propanol, n-butanol, isopropanol, isobutanol, tert-butanol, pentanol, hexanol, and mixtures thereof, even more preferentially chosen from n-butanol, ethanol, and mixtures thereof, most preferentially ethanol.

[0162] Preferably, the polar and / or protic solvent(s) are present in composition (C) in a total weight content ranging from 1% to 99% by weight, preferably ranging from 10% to 80% by weight, relative to the total weight of composition (C).

[0163] According to a particular embodiment, composition (C) comprises one or more oils different from the compounds A, preferably chosen from hydrocarbon-based oils, more preferentially chosen from C8-C16hydrocarbon-based oils, even more preferentially chosen from isoalkanes, and better still chosen from C13-C16isoparaffins, isododecane, isohexadecane, and mixtures thereof, and even better still isododecane.

[0164] The term “oil” means a water-immiscible non-aqueous compound that is liquid at room temperature (20°C) and at atmospheric pressure (760 mmHg).

[0165] The term “hydrocarbon-based oil” means an oil formed essentially from, or even consisting of, carbon and hydrogen atoms, and possibly oxygen and nitrogen atoms, and not containing any silicon or fluorine atoms. It may contain alcohol, ester, ether, carboxylic acid, amine and / or amide groups.

[0166] Preferably, the oil(s) different from the compounds A are present in composition (C) in a total weight content ranging from 1% to 90% by weight, preferably ranging from 20% to 80% by weight, relative to the total weight of composition (C).

[0167] According to a preferred embodiment, composition (C) is an anhydrous composition.

[0168] The term “anhydrous composition” refers to a composition comprising an amount of less than 5% by weight of water, preferably less than 3% by weight of water, more preferentially less than 1% by weight of water, relative to the total weight of the composition in question; and better still, the composition under consideration is free of water. Where appropriate, such small amounts of water may notably be introduced by ingredients of the composition that may contain residual amounts thereof.

[0169] Composition (C) may be in any presentation form conventionally used for haircare application. In a nonlimiting manner, composition (C) may be in the form of a lotion, a cream, a mousse, a gel, a spray or a lacquer.

[0170] Preferably, composition (C) is used as a leave-on application.

[0171] Composition (C) may be in the form of a mask, a conditioning composition or a care composition. Composition (C) may also be in the form of a composition to be added to or mixed with a mask or a conditioning composition before application.

[0172] Composition (C) may be packaged in a pump bottle or in an aerosol container, so as to apply composition (C) in vaporized (lacquer) or foam form. In these cases, composition (C) preferably comprises at least one propellant.

[0173] According to a preferred embodiment, composition (C) comprises a total content of coloring agents of less than 0.1% by weight, preferably less than 0.01% by weight, more preferentially less than 0.001% by weight relative to the total weight of composition (C); even more preferentially, the composition is free of coloring agents.

[0174] The term “coloring agent” means an oxidation dye, a direct dye or a pigment.

[0175] The term “oxidation dye” means an oxidation dye precursor chosen from oxidation bases and couplers. Oxidation bases and couplers are colorless or sparingly colored compounds, which, via a condensation reaction in the presence of an oxidizing agent, give a colored species.

[0176] The term “direct dye” means a natural and / or synthetic dye, including in the form of an extract or extracts, other than oxidation dyes. These are colored compounds that will spread superficially on the fiber.They may be ionic or nonionic, i.e. anionic, cationic, neutral or nonionic.

[0177] According to a preferred embodiment, composition (C) comprises a total content of silicones of less than 0.1% by weight, preferably less than 0.01% by weight, more preferentially less than 0.001% by weight relative to the total weight of the composition; even more preferentially, composition (C) is free of silicones.

[0178] According to a preferred embodiment, composition (C) comprises a total content of cationic polymers of less than 0.1% by weight, preferably less than 0.01% by weight, more preferentially less than 0.001% by weight relative to the total weight of the composition; even more preferentially, composition (C) is free of cationic polymers.

[0179] The term “cationic polymer” means any non-silicone polymer (not comprising silicon atoms) containing cationic groups and / or groups that can be ionized into cationic groups, and not containing any anionic groups and / or groups that can be ionized into anionic groups.Examples

[0180] The examples that follow will allow the invention to be understood more clearly, without, however, being limiting in nature.

[0181] Example A: Synthesis of castor oil bearing an acetoacetate function (Compound 1)

[0182] The synthesis is represented by the following preparation scheme:

[0183] 50 g of castor oil (sold by the company Interchimie) and 25.40 g of tert-butyl acetoacetate are placed in a 250 mL SVL®reactor equipped with a mechanical stirrer, a thermometer and a distillation column. The reaction medium is heated at 130°C on an oil bath. After 7 hours, the reaction medium is cooled, placed in a 250 ml pear-shaped flask and heated at 120°C under continuous vacuum on a rotavapor for 1 hour. A slightly yellow oil is obtained.Examples 1 to 5: Examples of application to locks

[0184] The following compositions were prepared from the contents indicated in the tables below. The contents are expressed as weight percentages relative to the total weight of the composition under consideration.Compositions A1 and A2

[0185] IngredientsA1(Invention)A2(Comparative)Compound 1 of Example A0.5Castor oil sold by the company Interchimie-0.5Ethanolqs 100qs 100Composition B

[0186] IngredientsBJeffamine T403Polyetheramine (Mw = 440 g / mol)AHEW (81 g / eq)0.25Ethanolqs 100Reference composition R1

[0187] IngredientsR1Ethanolqs 100Application and evaluation protocol

[0188] Five locks of type IV hair weighing 2.7 g were first washed with shampoo.

[0189] Composition A1 was applied to a first lock in a bath ratio of 0.5 g of composition A1 per 1 g of hair.

[0190] Composition A2 was applied to a second lock in a bath ratio of 0.5 g of composition A1 per 1 g of hair.

[0191] A composition C1 was prepared by mixing 1 part by weight of composition A1 with 1 part by weight of composition B and then applied to a third lock in a bath ratio of 1 g of composition C1 per 1 g of hair.

[0192] A composition C2 was prepared by mixing 1 part by weight of composition A2 with 1 part by weight of composition B and then applied to a fourth lock in a bath ratio of 1 g of composition C1 per 1 g of hair.

[0193] The fifth lock was a control lock to which only the reference composition R1 was applied in a bath ratio of 1 g of reference composition R1 per 1 g of hair.

[0194] The various compositions were applied to damp hair laid flat on aluminum foil. After applying the compositions, the locks were squeezed dry by finger, dried on Kimtech absorbent paper and then hung in the open air until totally dry. The locks were then hung in an oven at 60°C for 20 minutes and then in an oven at 25°C and 80% relative humidity for 24 hours.

[0195] The development of frizziness and volume was monitored using an apparatus designed by the company Bossa Nova, called Bolero Lite, with a measurement at T0 after treatment with the composition, drying and then placing in an oven at 60°C for 20 minutes and a measurement after 24 hours in an oven at 25°C and 80% relative humidity.

[0196] The Bolero Lite machine is a 2D image capture and analysis system designed to discriminate quickly and efficiently on a lock of hair between the fibers corresponding to frizziness and those forming part of the body of the lock. By using a uniform backlight, it was possible to measure the variations in light transmission through the hair sample with a standard black and white image and thus evaluate hair density. For each pixel in the image, the transmitted light was measured.

[0197] If the transmission:

[0198] ▪ was below a defined threshold, this corresponds to a high density area and the pixel may be defined as forming part of thebody / volume of the lock;

[0199] ▪ was above the defined threshold, this is a low density area and the pixel may be defined as forming part of thefly-away / frizziness;

[0200] ▪ was above the sensitivity threshold, the perceived signal was considered to benoise. It was thus not taken into account.

[0201] In the context of our study, the defined threshold was set at 50% and the sensitivity threshold was set at 95%.

[0202] The Bolero Lite image analysis software made it possible to obtain the value for the body surface area and the frizziness surface area (in cm2) of each of the locks tested.Results of the evaluation:

[0203] The results of the measurements of frizziness area (in cm2) are summarized in the table below:

[0204] ExamplesComposition testedFrizziness area at T0(in cm2)Frizziness area at T0 + 24H 80% RH(in cm2)1(Invention)A119.51933.6492(Comparative)A212.61942.5483(Invention)C111.5323.5674(Comparative)C210.7783.8825(Control)R152.967.7

[0205] The use of the compounds according to the invention makes it possible to limit the formation of frizziness and the increase in volume of the head of hair in a humid environment.

Claims

The use of one or more compounds A optionally combined with one or more (poly)amine compounds or of a composition (C) comprising the compound(s) A and optionally the (poly)amine compound(s), for protecting keratin fibers from moisture, preferably for limiting the formation of frizziness and / or the increase in volume of the head of hair in a humid environment, the compound(s) A being chosen from the compounds of formula (I), the optical or geometrical isomers thereof, the solvates thereof, such as hydrates, and mixtures thereof:(I)in which formula (I):- Z represents a linear or branched, saturated or unsaturated, conjugated or non-conjugated, acyclic or cyclic, aromatic or non-aromatic multivalent C2to C40, in particular C3to C36, hydrocarbon-based radical, Z possibly being interrupted with one or more groups or heteroatoms chosen from -O-, -N(Ra)-, -S-, -C(O)-, (hetero)cycles, and combinations thereof;- AK1 represents a divalent saturated or unsaturated, linear or branched C1-C12, preferably C1-C6, more preferentially saturated C1-C6, hydrocarbon-based chain;- AK2 represents a linear or branched, saturated or unsaturated, C1-C40monovalent hydrocarbon-based chain, optionally substituted with one or more identical or different radicals chosen from -OR, -X-AK3-(O-C(O)-C(Ra)(Rb)-C(O)-R4)v; and / or said chain being optionally interrupted with one or more heteroatoms or groups chosen from -O-, -S-, -C(O)-, (hetero)cycle(s), and combinations thereof, in particular -O-C(O)-, -C(O)-O- and / or -(hetero)cycle-O-(hetero)cycle-;- AK3 represents a divalent linear or branched, saturated or unsaturated C1-C12, preferably C1-C6, more preferentially saturated C1-C6, even more preferentially C1-C4, hydrocarbon-based chain;- R represents a hydrogen atom, a linear or branched, saturated or unsaturated C1-C6, preferably C1-C4, alkyl radical, in particular a methyl radical, or a radical -C(O)-C(Ra)(Rb)-C(O)-R4;- X represents -O-, -S-, -O-C(O)- or -C(O)-O-;- Y represents -O-C(O)- or -C(O)-O-;- R4represents a linear or branched, saturated or unsaturated C1-C6monovalent hydrocarbon-based radical, preferably a (C1-C4)alkyl group, in particular methyl or tert-butyl, more preferentially methyl;- Raand Rb, which may be identical or different, represent a hydrogen atom or a (C1-C4)alkyl group, preferably a hydrogen atom;- p denotes an integer equal to 0 or 1;- m denotes an integer equal to 0, 1, 2, 3 or 4; it being understood that when m is greater than 1, then the radicals -Y-AK2are 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-(AK1)q-(O-C(O)-C(Ra)(Rb)-C(O)-R4)uare identical or different;- t 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 groups -C(O)-C(Ra)(Rb)-C(O)-R4.The use as claimed in claim 1, in which the compound(s) A are chosen from the compounds of formula (I), the optical or geometrical isomers thereof, the solvates thereof, such as hydrates, and mixtures thereof,in which formula (I):- 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, saturated or unsaturated, C12-C24monovalent hydrocarbon-based chain, optionally substituted with one or more identical or different radicals chosen from -OR, -X-AK3-(O-C(O)-C(Ra)(Rb)-C(O)-R4)v; and / or said chain being optionally interrupted with one or more heteroatoms or groups chosen from -O-, -S-, -C(O)-, epoxides, and combinations thereof, in particular -O-(CO)- or -C(O)-O-;- Y, AK3, v, R, X, R4, Raand Rbbeing as defined in claim 1;it being understood that the compounds of formula (I) contain at least two radicals -C(O)-C(Ra)(Rb)-C(O)-R4.The use as claimed in either of the preceding claims, in which the compound(s) A are chosen from compounds (1), (2), (3), (4), (7), (8), (9), (11) and (16) below, the optical or geometrical isomers thereof, the solvates thereof such as hydrates, and mixtures thereof:(1)(2)(3)(4)(7)(8)(9)(11)(16);preferably from the compounds (4), the optical or geometrical isomers thereof, the solvates thereof, such as hydrates, and mixtures thereof.The use as claimed in any one of the preceding claims, in which the composition (C) comprises a total content of compounds A ranging from 0.005% to 5% by weight, preferably ranging from 0.1% to 3% by weight, more preferentially ranging from 0.1% to 2% by weight relative to the total weight of composition (C).The use as claimed in any one of claims 1 to 3, in which the compound(s) A are used in combination with one or more (poly)amine compound(s), the (poly)amine compound(s) preferably being applied to the keratin fibers before, after or at the same time as the compound(s) A.The use as claimed in any one of claims 1 to 4, in which composition (C) comprises the compound(s) A and one or more (poly)amine compounds.The use as claimed in claim 5 or 6, in which the (poly)amine compound(s) are chosen from:ia) (poly)amine compounds including more than three primary and / or secondary amine groups, preferably primary (NH2), in particular chitosans such as poly(D-glucosamine) and polylysine,ib) polyether diamines, in particular polyethylene glycol α,ω-diamines, bearing a chain-end amine function,ic) polyether triamines,id) aminoalkoxysilanes, in particular APTES,ie) polyamine compounds NH2-alk-NH2, in which alk denotes a divalent C2-C20hydrocarbon-based chain, optionally interrupted with one or more heteroatoms chosen from -O-, -N(R)- with R denoting a hydrogen atom or a C1-C4alkyl radical, notably spermidine and 4,7,10-trioxa-1,13-tridecanediamine, andif) polydialkylsiloxanes comprising primary amine groups at the end of the chain or on side chains, in particular polydimethylsiloxanes comprising primary amine groups, more particularly bis(3-aminopropyl)-terminated poly(dimethoxysiloxane) (PDMS-diNH2) and amodimethicones comprising amine groups on side chains, more particularly bis-cetearyl amodimethicone;preferably from ic) polyether triamines.The use as claimed in claim 6 or 7, in which composition (C) comprises a total content of (poly)amine compounds ranging from 0.005% to 5% by weight, preferably ranging from 0.1% to 3% by weight, more preferentially ranging from 0.1% to 2% by weight relative to the total weight of composition (C).The use as claimed in any one of claims 1 to 4 or 6 to 8, in which composition (C) comprises one or more polar and / or protic solvents, preferably chosen from monoalcohols containing from 2 to 6 carbon atoms, more preferentially chosen from ethanol, propanol, n-butanol, isopropanol, isobutanol, tert-butanol, pentanol, hexanol, and mixtures thereof, even more preferentially chosen from n-butanol, ethanol, and mixtures thereof, most preferentially ethanol.The use as claimed in the preceding claim, in which composition (C) comprises a total content of polar and / or protic solvents ranging from 1% to 99% by weight, preferably ranging from 10% to 80% by weight relative to the total weight of composition (C).The use as claimed in any one of claims 1 to 4 or 6 to 10, in which composition (C) is an anhydrous composition.The use as claimed in any one of claims 6 to 11, in which composition (C) is obtained by extemporaneous mixing of a composition (A) comprising the compound(s) A with a composition (B) comprising the (poly)amine compound(s).

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