Use of a compound with acetoacetate functions optionally associated with a (poly)amine compound or a composition comprising it or them to protect keratin fibers from humidity

Abstract

The present invention relates to the use of at least one compound with acetoacetate functions optionally combined with at least one (poly)amine compound or a composition comprising it or them to protect keratin fibers from humidity.

Description

Title of the invention: Use of a compound with acetoacetate functions optionally associated with a (poly)amine compound or of a composition comprising it or them to protect keratin fibers from humidity Technical field of the invention

[0001] The present invention relates to the use of at least one compound with acetoacetate functions optionally combined with at least one (poly)amine compound or a composition comprising it or them to protect keratin fibers from humidity. Background to the invention

[0002] Due to their nature, certain types of hair are more sensitive to humidity and can therefore tend to form frizz, which can cause an increase in the volume of the hair. These types of hair are particularly difficult to style in humid environments.

[0003] In order to remedy this, it is usual to use hair compositions based on silicone raw materials which can however give a greasy and heavy appearance to the touch or based on oils whose conditioning effect can tend to fade quickly over time, being in particular not very resistant to external aggressions, in particular to shampoos.

[0004] Furthermore, the formulation of environmentally friendly cosmetic products, i.e. those whose design and development take environmental issues into account, is becoming a major concern to help meet global challenges. It is therefore essential to offer more sustainable compositions that can meet these environmental challenges, in particular by reducing the use of compounds of petrochemical origin.

[0005] Thus, there is a real need to find a way of remedying these drawbacks, in particular to facilitate the styling of hair in a humid environment by lastingly limiting the formation of frizz and / or the increase in volume of the hair in a humid environment, the observed effect being particularly persistent after at least one shampoo.

[0006] The applicant has surprisingly discovered that all or part of these objectives can be achieved by the use of at least one compound with acetoacetate functions optionally combined with at least one (poly)amine compound or a composition comprising it or them to protect keratin fibers from humidity. Summary of the invention

[0007] The 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) to protect keratin fibers from humidity, preferably to limit the formation of frizz and / or the increase in volume of the hair in a humid environment, the compound(s) A being chosen from the compounds of formula (I), their optical and geometric isomers, their solvates such as hydrates, and their mixtures: (I) (H)p--Z- (Y-AO^ [(O)HAKj)< r ^ formula (I) in which: - Z represents a multivalent hydrocarbon radical from C2 to C40, in particular from 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 combinations thereof; - AK1 represents a linear or branched divalent hydrocarbon chain saturated or unsaturated in C1-C12, preferably in C1-C6, more preferably saturated in C1-C6; - AK2 represents a linear or branched, saturated or unsaturated, monovalent hydrocarbon chain, 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 combinations thereof, 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 C1-C6, more preferably saturated in C1-C6, even more preferably in C1-C4; - R represents a hydrogen atom, a linear or branched saturated or unsaturated C1-C6, preferably C1-C4, alkyl radical, in particular methyl, or a radical -C(O)-C(Ra)(Rb)-C(O)-R4; - X represents -O-, -S-, -OC(O)- or -C(O)-O-; - Y represents -OC(O)- or -C(O)-O-; - Rj represents a monovalent C1 to C6 hydrocarbon radical, linear or branched, saturated or unsaturated, preferably a (C1-C4) alkyl group, in particular methyl or tert-butyl, more preferably methyl; - Ra and Rb, identical or different, represent a hydrogen atom or a group (CrC4)alkyl, 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 -(0)t-(AKi)q-(0-C(0)-C(Ra)(Rb)-C(0)-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. Detailed description of the invention

[0008] For the purposes of the present invention, and unless otherwise indicated:

[0009] ■ by "keratin fibers" we mean fibers of human or animal origin such as than 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.

[0010] ■ by "(hetero)aryl" we mean aryl or heteroaryl groups.

[0011] ■ by "(hetero)cycloalkyl" we mean cycloalkyl or heterocycloalkyl groups.

[0012] ■ the “aryl” or “heteroaryl” radicals or the aryl or heteroaryl part of a radical can be substituted by at least one substituent carried by a carbon atom, chosen from: - a (poly)(hydroxy)alkyl radical in C1-C6, preferably in C1-C4; - a halogen atom such as chlorine, fluorine or bromine; - a hydroxy group; - a C1-C2 alkoxy radical; a C2-C4 (poly)-hydroxyalkoxy radical; - an amino radical; - an amino radical substituted by one or two alkyl radicals, identical or different, in C1-C6, C1-C6, preferably in C1-C4; - an acylamino radical (-N(R)-C(O)-R') in which the radical R is a hydrogen atom; - a CrC4 alkyl radical and the radical R' is a CrC4 alkyl radical; a carbamoyl radical ((R)2N-C(O)-) in which the radicals R, identical or not, represent a hydrogen atom, a C1-C4 alkyl radical; - an alkylsulfonylamino radical (R'-S(O)2-N(R)-) in which the radical R represents a hydrogen atom, a C1-C4 alkyl radical and the radical R' represents a C1-C4 alkyl radical, a phenyl radical; - an aminosulfonyl radical ((R)2N-S(O)2-) in which the radicals R, identical or not, represent a hydrogen atom, a CrC4 alkyl radical; - a carboxylic radical in acid or salified form (preferably with an alkali metal or an ammonium, substituted or not); - a cyano group (CN); - a polyhalogeno(Ci-C4)alkyl group, preferably trifluoromethyl (CF3).

[0013] ■ the cyclic or heterocyclic part of a non-aromatic radical can be substituted by at least one substituent carried by a carbon atom chosen from the groups: - hydroxy; - CrC4 alkoxy, (poly)hydroxy C2-C4 alkoxy; - alkylcarbonylamino ((RC(O)-NR'-) in which the radical R' is a hydrogen atom, a C1-C4 alkyl radical and the radical R is a C1-C2 alkyl radical, amino substituted by one or two identical or different C1-C4 alkyl groups; - alkylcarbonyloxy ((RC(O)-O-) in which the radical R is a C1-C4 alkyl radical, amino substituted by one or two identical or different C1-C4 alkyl groups; - alkoxycarbonyl ((ROC(O)-) in which the radical R is a CrC 4 alkyl radical, amino substituted by one or two identical or different CrC4 alkyl groups

[0014] ■ a cyclic, heterocyclic radical, or a non-aromatic part of an aryl radical or heteroaryl, may also be substituted by one or more oxo groups.

[0015] ■ a hydrocarbon chain is unsaturated when it contains one or more double bonds and / or one or more triple bonds.

[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 cycle 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 from 5 to 14 links, from 1 to 6 heteroatoms chosen from the nitrogen, oxygen, sulfur and selenium atom, and of which at least one cycle is aromatic; preferably a heteroaryl radical is chosen from acridinyl, benzimidazolyl, benzobistriazolyl, benzopyrazolyl, benzopyridazinyl, benzo- quinolyl, benzothiazolyl, benzotriazolyl, benzoxazolyl, pyridinyl, tetrazolyl, di-hydrothiazolyl, imidazopyridinyl, imidazolyl, indolyl, isoquinolyl, naphthoimi-dazolyl, naphthooxazolyl, naphthopyrazolyl, oxadiazolyl, oxazolyl, oxazolo-pyridyl, phenazinyl, phenooxazolyl, pyrazinyl, pyrazolyl, pyrilyl, pyrazoyl-triazyl, pyridyl, pyridinoimidazolyl, pyrrolyl, quinolyl, tetrazolyl, thiadiazolyl, thiazolyl, thiazolopyridinyl, thiazoylimidazolyl, thiopyrylyl, triazolyl, xanthylyl.

[0018] ■ 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 contain from 1 to several unsaturations, preferably the cycloalkyl is a cyclohexyl group.

[0019] ■ a "heterocyclic" or "heterocycloalkyl" radical is a non-cyclic radical mono or polycyclic aromatic, condensed or not, containing from 3 to 9 members, comprising from 1 to 4 heteroatoms chosen from the nitrogen, oxygen, sulfur and selenium atom, preferably the heterocycloalkyl is chosen from epoxide, pi-perazinyl, piperidinyl, morpholinyl, or dithiolane.

[0020] ■ an "alkyl" radical is a saturated, linear or branched hydrocarbon radical, in particular particularly in C1-C6, preferably in C1-C4.

[0021] ■ an "alkoxy" radical is an alkyloxy radical for which the alkyl radical is a hydrocarbon radical, linear or branched, in C1-C6 preferentially in C1-C4.

[0022] ■ a "(poly)(hydroxy)alkyl" radical denotes a C1-C6 alkyl radical, of preferably C1-C4 optionally substituted by one or more hydroxy radicals, preferably substituted by 1 to 4 hydroxy groups, more particularly between 1 and 3.

[0023] ■ the "solvates" represent the hydrates as well as the association with alcohols linear or branched CrC4 linear or branched such as ethanol, isopropanol, n-propanol.

[0024] The expressions “between ... and ...”, “includes from ... to ...”, “formed from ... to ...”, and “ranging from ... to ...” must be understood inclusively, unless otherwise specified.

[0025] The expressions "at least one" and "one or more" are synonymous and can be used interchangeably. Use

[0026] The subject of the present invention is the use of the compound(s) A as defined above, 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 compounds to protect keratin fibres from humidity, preferably to limit the formation of frizz and / or the increase in volume of the hair in a humid environment.

[0027] The applicant has found, surprisingly, that the compound(s) A even actually associated with one or more (poly)amine compounds, or the composition (C) comprising it or them would make it possible to facilitate the styling of keratin fibers in a humid environment and in particular to limit the formation of frizz and / or the increase in volume of the hair in a humid environment, the observed effect being able to be persistent after at least one shampoo.

[0028] According to a first particular embodiment, the compound(s) A are used alone, i.e. not associated with one or more (poly)amine compounds or the composition (C) does not comprise a (poly)amine compound.

[0029] According to a second particular embodiment, the compound(s) A are used in association with one or more (poly)amine compounds.

[0030] 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.

[0031] Alternatively, according to this second particular embodiment, the (poly)amine compound(s) may be applied to the keratin fibers before the compound(s) A.

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

[0033] According to this second particular embodiment, the (poly)amine compound(s) may be included in a composition (B) separate from the composition (C) comprising the compound(s) A, the composition (B) preferably being applied to the keratin fibers before, after or at the same time as the composition (C). Alternatively, according to this second particular embodiment, the composition (B) may be applied to the keratin fibers before the composition (C). Alternatively, according to this second particular embodiment, the composition (B) may be applied to the keratin fibers after the composition (C).

[0034] According to another particular embodiment, the composition (C) comprises the compound(s) A and one or more (poly)amine compounds.

[0035] According to this other particular embodiment, the composition (C) can 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

[0036] The compound(s) A are chosen from the compounds of formula (I), their optical and geometric isomers, their solvates such as hydrates, and their mixtures.

[0037] According to a preferred embodiment, the compound(s) A are chosen from the compounds of formula (I), their optical and geometric isomers, their solvates such as hydrates, and their mixtures, such that Z denotes a radical chosen from: a) divalent radicals, preferably C2-C30, optionally 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 denote independently of each other 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-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.

[0038] According to a preferred embodiment, a (hetero)cycle denotes a divalent heterocyclic radical (i.e. a heterocycle), preferably a heterocycloalkyl radical, more particularly a divalent heterocycloalkyl radical comprising 3, 5 or 6 links such as a divalent epoxide radical, a divalent tetrahydrofuran radical or a divalent tetrahydropyran 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).

[0039] According to a preferred embodiment, AK2 represents a linear or branched, saturated or unsaturated monovalent hydrocarbon chain, C12-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-.

[0040] According to a first preferred embodiment variant, the compound(s) A are chosen from the compounds of formula (I), their optical and 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, saturated or unsaturated monovalent hydrocarbon chain, C12-C24j, 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 combinations thereof, in particular -O(CO)- or -C(O)-O-; - Y, AK3, v, R, X, R4, Ra and Rb being as previously defined for the formula (i); it being understood that the compounds of formula (I) contain at least 2 radicals -C(O)-C(Ra)(Rb)-C(O)-R4.

[0041] According to a preferred embodiment, AK2 represents a linear or branched, saturated or unsaturated monovalent hydrocarbon chain, C12-C24j, 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 combinations thereof, in particular -OC(O)- or -C(O)-O-.

[0042] According to this first preferred embodiment variant, the compound(s) A are preferably chosen from the following compounds (1), (2), (3), (4), (7), (8), (9), (11) and (16), their optical and geometric isomers, their solvates such as hydrates, and their mixtures: (1) (11)

[0043] According to this first preferred embodiment variant, the compound(s) A are more preferably chosen from compounds (4), their optical and geometric isomers, their solvates such as hydrates, and their mixtures.

[0044] According to a second embodiment variant, the compound(s) A are chosen from the compounds of formula (I), their optical and geometric isomers, their solvates such as hydrates, and their mixtures, such as: - p is equal to 0; - Z represents a multivalent hydrocarbon radical from C4 to C24, particularly from C6 to C2o, more particularly from C1 to C20, in particular Cp, linear or branched, saturated or unsaturated, preferably saturated, 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; - 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, saturated or unsaturated, preferably saturated, monovalent hydrocarbon chain 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 combinations thereof, 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 as defined previously for formula (I);

[0045] 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 variant, the compound(s) A are preferably chosen from compounds (5) and (6) below, their optical and geometric isomers, their solvates such as hydrates, and their mixtures: (5)

[0046] According to a third embodiment variant, the compound(s) A are chosen from the compounds of formula (I), their optical and 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, hydrocarbon radical from C2 to C24, particularly from C3 to C10, in particular C3, unsubstituted and uninterrupted, linear or branched, saturated or unsaturated, preferably saturated and acyclic; - AK2 independently represent a linear or branched, saturated or unsaturated, preferably saturated, monovalent hydrocarbon chain of C12-C24, preferably C16-C20, in particular C[8, 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 optionally interrupted by one or more heteroatoms or groups chosen from -O-, -S-, -C(O)-, (hetero)cycle(s), and combinations thereof, 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 C1-C6, more preferably saturated in C1-C6, even more preferably in C2-C4, better still in C3; - 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, 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.

[0047] According to a preferred embodiment, m is equal to 3, n is equal to 1 and u is equal to 1.

[0048] According to a preferred embodiment, t is equal to 0.

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

[0050] According to a preferred embodiment, Y denotes -C(O)-O.

[0051] According to a preferred embodiment, none of the AK2 radicals are interrupted.

[0052] According to a preferred embodiment, the AK2 radicals are saturated.

[0053] According to a preferred embodiment, the AK2 radicals are not substituted by - GOLD.

[0054] According to a preferred embodiment, AK3 represents a linear or branched divalent hydrocarbon chain saturated or unsaturated in C1-C6, more preferably saturated in C1-C6, even more preferably saturated in C1-C4, better saturated in C3.

[0055] According to this third embodiment variant, the compound(s) A are in particular chosen from the compounds (10) below, their optical and geometric isomers, their solvates such as hydrates, and their mixtures: (10).

[0056] According to a fourth embodiment variant, the compound(s) A are chosen from the compounds of formula (I), their optical and geometric isomers, their solvates such as hydrates, and their mixtures, such as: - p is equal to 1; - Z represents a multivalent hydrocarbon radical from C2 to C24, particularly from C4 to C20, preferably from 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, saturated or unsaturated, preferably saturated, monovalent hydrocarbon chain in C8-C30, preferably in C10-C29, 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 -OR; and / or said chain being optionally interrupted by one or more heteroatoms or groups chosen from -O-, -S-, -C(O)-, (hetero)cycle(s), and combinations thereof, 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 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.

[0057] According to a preferred embodiment, n is equal to 0 and m is equal to 1.

[0058] According to a preferred embodiment, Z is a divalent radical.

[0059] 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.

[0060] According to this fourth embodiment variant, the compound(s) A are in particular chosen from the compounds of formula (Ie), their optical and geometric isomers, their solvates such as hydrates, and their mixtures: HZY-AK4-Y'-ZH (lie) formula (lie) in which: - Y is 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 denotes 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.

[0061] According to this fourth embodiment variant, the compound(s) A are in particular chosen from compounds (12) and (15) below, their optical and geometric isomers, their solvates such as hydrates, and their mixtures: (12) (15).

[0062] According to a fifth embodiment variant, the compound(s) A are chosen from the compounds of formula (I), their optical and geometric isomers, their solvates such as hydrates, and their mixtures, such as: - p is equal to 0; - Z represents a tetravalent hydrocarbon radical of C2 to C24, in particular of C3 to C10, preferably of C4 or of C5, linear or branched, saturated or unsaturated, preferably saturated and acyclic, Z being further substituted by one or more radicals -[(O)t -(AKl)q-(0-C(0)-C(Ra)(Rb)-C(0)-R4)u]n, preferably n being equal to 1; - n + m is equal to 4, preferably m is equal to 3; - AK2 independently represents a linear or branched hydrocarbon chain, saturated or unsaturated, preferably saturated, from C1 to C30, preferably from C16 to C24, preferably from 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 combinations thereof, 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 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.

[0063] According to a preferred embodiment, t is equal to 0 and u is equal to 1.

[0064] According to a preferred embodiment, all the AK2 radicals are identical, and preferably, all Y radicals are identical.

[0065] According to a preferred embodiment, Y denotes -OC(O)-.

[0066] According to a particular embodiment, the compounds according to this fifth variant are in particular chosen from the compounds of formula (lid), their optical and 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(Iid) formula (lid) in which: - AK'2 represents a linear or branched monovalent hydrocarbon chain, preferably linear, saturated or unsaturated, preferably saturated, in C14-C30, preferably in C16-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(0)-R4)v, preferably substituted by one or more -OR radicals; - AK3, v, R, R4, Ra and Rb being as defined previously for formula (I); it being understood that said compounds contain at least 2 radicals C(O)-C(Ra)(Rb j-QOj-R,.

[0067] According to a sixth embodiment variant, the compound(s) A are chosen from the compounds of formula (I), their optical and 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 from C2 to C24, in particular from C3 to C12, linear or branched, saturated or unsaturated, conjugated or not, preferably unconjugated, acyclic or cyclic, aromatic or not, preferably non-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 combinations thereof; - AK2 represents a linear or branched, saturated or unsaturated, preferably saturated, monovalent hydrocarbon chain of C14-C30, preferably C14-C24, preferably C17, 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 combinations thereof, in particular -OC(O)-, -C(O)-O- or -(hetero)cycle-O-(hetero)cycle-, preferably optionally interrupted by -OC(O)- or -C(O)-O-, and more preferably being uninterrupted; - X is as defined previously for formula (I), and preferably X denotes a sulfur atom; - Y, AK1, AK3, v, t, q, u, R, R4, Ra and Rb being 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.

[0068] 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 heterocycloalkyl radical comprising 5 or 6 members, 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).

[0069] According to this sixth embodiment variant, the compound(s) A are in particular chosen from the compounds of formula (Ie), their optical and 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 (lie) formula (lie) 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 heterocycloalkyl radical comprising 5 or 6

[0070] links substituted 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, saturated or unsaturated, preferably saturated, monovalent hydrocarbon chain of C14-C30, preferably C14-C24, preferably Cp, said chain being optionally substituted by one or more identical or different radicals chosen from -OH, -O-C(O)-C(Ra)(Rb)-C(O)-R4) 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 chosen from -O-, -S-, -C(O)-, (hetero)cycle(s), and combinations thereof, 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. According to this sixth embodiment variant, the compound(s) A are in particular chosen from the compounds (14) below, their optical and geometric isomers, their solvates such as hydrates, and their mixtures: V

[0071] (14) with W being a hydrogen atom or -C(O)-C(Ra)(Rb)-C(O)-R4, and said compound containing at least two -C(O)-C(Ra)(Rb)-C(O)-R4 groups. Preferably, the compound(s) A are chosen from the compounds of formula (Ia), their optical and 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 designate a linear or branched, saturated or unsaturated monovalent hydrocarbon chain, C12-C24, optionally substituted by one or several identical or different radicals chosen from -OR and -X-AK3-(O-C(O)-C(R a)(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 -OC(O)- and -C(O)-O-; - Y, AK3, v, R, X, R4, Ra and Rb being as defined previously for formula (I), preferably Y denotes -OC(O); it being understood that the compounds of formula (la) contain at least 2 C(O)-C(Ra)(Rb)-C(O)-R4 radicals.

[0072] Preferably, the compound(s) A are chosen from the compounds of formula (Ib), their optical and 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 as defined previously for formula (I); - Z represents a tetravalent hydrocarbon radical of C2 to C24, in particular of C3 to C10, preferably of C3, unsubstituted and uninterrupted, linear or branched, saturated or unsaturated, preferably saturated and acyclic; - AK2 independently represent a linear or branched, saturated or unsaturated, preferably saturated, monovalent hydrocarbon chain of C12-C24, preferably C16-C20, preferably C[8, optionally substituted by one or more identical or different radicals chosen from -OR, -X-AK3-(OC(O)-C(Ra)(Rb)-C(O)-R4)v, preferably substituted by one or more radicals -X-AK3-(OC(O)-C(Ra)(Rb)-C(O)-R 4)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 combinations thereof, in particular -OC(O)-, -C(O)-O- or -(hetero)cycle-O-(hetero)cycle-, preferably being uninterrupted; - AK3 represents a linear or branched divalent hydrocarbon chain saturated or unsaturated in CrCi2, preferably in Ci-C6, more preferably saturated in Ci-C6, even more preferably in C2-C4, preferably in C3; - v is as defined 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, Ra and Rb being 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.

[0073] Preferably, the compound(s) A are chosen from the compounds of formula (Ic), their optical and geometric isomers, their solvates such as hydrates, and their mixtures: m(AK2 -Y) - ZH - [(0)t-(AKl)q-(0-C(0)-C(Ra)(Rb)-C(0)-R4)u]n (the) formula (the) in which: - Z represents a multivalent hydrocarbon radical from C1 to C24, particularly from C16 to C20 such as Cp, linear or branched, saturated or unsaturated, preferably saturated and acyclic, Z being further optionally substituted by one or more radicals -[(O) t-(AKl)q-(OC(O)-C(Ra)(Rb)-C(O)-R4)u]n, preferably unsubstituted; - AK2 represents a linear or branched, saturated or unsaturated, preferably saturated, monovalent hydrocarbon chain of C14-C30, preferably C20-C29, substituted by one or more identical or different radicals chosen from -OR and -X-AK3-(OC(O)-C(Ra)(Rb)-C(O)-R4)v, preferably substituted by one or more -OR radicals; and / or said chain being optionally interrupted by one or more heteroatoms or groups chosen from -O-, -S-, -C(O)-, (hetero)cycle(s), and combinations thereof, 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 above 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 as defined previously for formula (I); it being understood that the compounds of formula (Ic) contain at least 2 radicals -C(O)-C(Ra)(Rb)-C(O)-R4.

[0074] Preferably, the compound(s) A are chosen from the compounds of formula (Id), their optical and 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 is equal to 4, preferably m is equal to 3; - Z represents a tetravalent hydrocarbon radical of C2 to C24, in particular of C3 to C10, in particular of 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, saturated or unsaturated, preferably saturated, monovalent hydrocarbon chain of C14-C30, preferably C16-C24, preferably Cp, said chain being optionally substituted by one or more identical or different radicals chosen from -OR or -X-AK3-(OC(O)-C(R a)(Rb)-C(O)-Ri)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 combinations thereof, 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 denotes a sulfur atom; Y, AK1, AK3, v, R, R4, 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.

[0075] Preferably, the compound(s) A are chosen from the compounds of formula (Ic), their optical and 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 as defined in claim 1, preferably n is zero; - Z represents a divalent hydrocarbon radical of C2 to C24, in particular of 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 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 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 in claim 1, and in particular -OH or -OC(O)-C(Ra)(Rb)-C(O)-R4); . - AK2 represents a linear or branched, saturated or unsaturated, preferably saturated, monovalent hydrocarbon chain of C14-C30, preferably C14-C24, preferably Cp, said chain being optionally substituted by one or more identical or different radicals chosen from -OR and -X-AK3-(OC(O)-C(Ra)(Rb)-C(O)-R4)v, preferably unsubstituted; and / or said chain being optionally interrupted by one or more heteroatoms or groups chosen from -O-, -S-, -C(O)-, (hetero)cycle(s), and combinations thereof, 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 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 as defined previously for formula (I); it being understood that the compounds of formula (Ic) contain at least 2 C(O)-C(Ra)(Rb)-C(O)-R4 radicals.

[0076] According to a preferred embodiment, the compound(s) A are chosen from the following compounds (1) to (16), their optical and geometric isomers, their solvates such as hydrates, and their mixtures: G 0 (1) / / V / N / "''x / Vx.--'' -Sx.''v $ AO .......' / -. / ..... (2) O ,-x '■'X; x ,, $ Y x *■ « v / • x ...S'A- X""""'' .-•X / x / 0 ....... v ô x"" ' 'J' / l (3) 0 OQO «A*. AA ï | & ts >A '■■Y' •■'X. -vx ,,.iww.v,.A -X * Ô ô * t 9 cAJk 0 0 G 0'^^- ° ï A f ? 0 ô / Ux V - (7) HaC Tl 28 with W being a hydrogen atom or -C(O)-C(Ra)(Rb)-C(O)-R4, and said compound containing at least two -C(O)-C(Ra)(Rb)-C(O)-R4 groups. Preparation of compounds of formula (I)

[0077] In particular, the compound(s) of formula (I), or (la), (Ib), (le), (Id), (le), (lie), (lid) or (lie), can be prepared by the succession of the following reactions: First step

[0078] 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 previously, under conditions known to those 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' denoting in particular -OH or -Cl; preferably R' denotes -OH; - AK'2 represents a linear or branched, unsaturated hydrocarbon chain, C1-C40, preferably C14-C20, said chain being optionally interrupted by one or more heteroatoms or groups chosen from -O-, -S-, -C(O)-, (hetero)cycle(s), and combinations thereof, in particular -OC(O)-, -C(O)-O- or -(hetero)cycle-O-(hetero)cycle-, preferably interrupted by -O- or -S-, more preferably being uninterrupted.

[0079] According to a preferred embodiment, m is equal to m'.

[0080] The polyols (H)pZ(OH)m can be cyclic or acyclic.

[0081] As examples of cyclic (H)pZ(OH)m polyols, mention may be made of maltose, lactose, raffinose, sucrose, trehalose, melibiulose, melibiose, mannobiose, kojibiose, nigerose, isomaltose, rutinose, rutinulose, xylobiose or sorbitan.

[0082] As examples of (H)pZ(OH)macyclic polyols, mention may be made of ethylene glycol, propylene glycol, butylene glycol, pentylene glycol, hexylene glycol, butanediol, glycerol, pentaerythritol, dipentaerythritol, trimethylolethan, mannitol, or trimethylolpropane.

[0083] 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 denotes glycerol.

[0084] The compounds R'CO-AK'2 are preferably unsaturated fatty acids of 15 to 36 carbon atoms, preferably of 15 to 24 carbon atoms. They can be mono or polyunsaturated.

[0085] The monounsaturated fatty acids are in particular chosen from palmitoleic acid, oleic acid, 9-eicosenoic acid, 11-eicosenoic acid, erucic acid and nervonic acid.

[0086] The polyunsaturated fatty acids are in particular chosen 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 in particular chosen from 10-Hydroxy-cis-12-octadecenoic acid, 10-Hydroxy-trans-1 1-octadecenoic acid, 12-Hydroxy-cis-9-octadecenoic acid, 13-Hydroxy-cis-9-octadecenoic acid, ricinoleic acid, isoricinoleic acid, and polyunsaturated hydroxy fatty acids in particular chosen from densipolic acid, auricolic acid, dimorphecolic acid.

[0087] More preferably, the unsaturated fatty acid is chosen from ricinoleic acid, oleic acid, palmitoleic acid, erucic acid and mixtures thereof. Second step

[0088] In a second step, all or part of the unsaturations of the radical(s) AK'2 are transformed a) via an epoxidation reaction into epoxide to lead to 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 carrying acid function(s) to lead to the derivatives (IV), such as for example the compound b3 illustrated in the scheme described below.

[0089] 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 preferably comprising from 1 to 6 carbon atoms, such as 3-mercapto-3-methylbutanol, 3-mercapto-2-butanol, or such as polyhydroxylated thiols, preferably comprising from 1 to 6 carbon atoms such as 3-mercapto-1,2 propanediol HS-CH(OH)-CH2OH.

[0090] 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 as defined previously for the compounds of formula (I). Third step

[0091] 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 C1-C4 such as methanol or ethanol, or a polyol to lead to compounds (IIIi), such as compound b2 illustrated in the diagram below, ii) carboxylic acids, preferably C1-C6, such as lactic acid, pyruvic acid, benzoic acid, glycolic acid or 2,2 bis hydroxymethyl pro-pionic acid, more preferably carboxylic acids substituted by at least one hydroxyl radical such as lactic acid, to lead to compounds (IIIi), such as compound b1 illustrated in the diagram below.

[0092] 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 even caffeine.

[0093] According to a preferred embodiment, the alcohol i) is chosen 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

[0094] In a fourth step, all or part of the alcohol functions -OH 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 radicals -OC(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 hydroxy radical or a (Ci-C4)alkoxy radical, such as methoxy, ethoxy, isobutoxy or t-butoxy.

[0095] According to a preferred embodiment, Gp-C(O)-C(Ra)(Rb)-C(O)-R4 denotes an ester chosen from ethyl acetoacetate, ethyl 2-methylacetoacetate, tert-butyl acetoacetate, preferably tert-butyl acetoacetate.

[0096] Compounds of structure (la), (le), such as compounds of structure (lie), compounds of structure (Id) and (le) can be obtained according to this method.

[0097] For example, step 4 can be implemented according to the protocol described in Trevino, A.S., & Trumbo, D.L. (2002). Acetoacetylated castor oil in coatings applications. Progress in Organic Coatings, 44(1), 49-54:

[0098] In certain cases, the compounds (H)pZ(OH)m' m (YAK'2)missus of 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 unsaturated fatty acids, optionally 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.

[0099] For example, starting from an unsaturated triglyceride, a thiol-ene reaction is carried out with a (poly)hydroxy thiol such as SH-(CH2)X OH with x being an integer preferably from 1 to 4, then a transesterification reaction (as described in Desroches, M., Caillol, S., Lapinte, V., Auvergne, R., & Boutevin, B. (2011). Synthesis of biobased polyols by thiol-ene coupling from vegetable oils. Macro-molecules, 44(8), 2489-2500: Conpcsè b3 Compound a3

[0100] 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 functions and (trans)esterification. A commercial epoxidized triglyceride can also be used as a raw material, such as the products offered by Arkema under the references Vikoflex 7170 or Vikoflex 7190.

[0101] As an example, the reaction scheme below can be implemented in which all the epoxides are opened by lactic acid and then each hydroxy is esterified by t-Bu-OCOCH2CH3, according to the scheme below: has) Compound a I Compound b 1 b)

[0102] Compound b I Compound c 1 As an example, we can also implement the reaction scheme below in which all the epoxides are opened by an alcohol, methanol in the example, then each hydroxy is esterified by t-Bu-OCOCH2CH3: has) Compound a2 Compound b2 b) Compound b2 Compound c2

[0103] The compounds of formula (la) to (le) can also be prepared by the following succession of reactions:

[0104] - 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 the conditions known to those skilled in the art to form an ester bond Y according to the scheme below: (H)pZ(COOH)m +mHO-AK'2 -> (H)pZ(COOH)m _m(YAK'2)m in which Y denotes -C(O)-O-, and AK'2 representing a linear or branched, unsaturated monovalent hydrocarbon chain, C1-C40, preferably C14-C2o, said chain being optionally interrupted by one or more heteroatoms or groups chosen from -O-, -S-, -C(O)-, (hetero)cycle(s), and combinations thereof, in particular -OC(O)-, -C(O)-O-, -(hetero)cycle-O-(hetero)cycle-, preferably interrupted by -O- or -S-, and more preferably not interrupted.

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

[0106] The polyacids (H)pZ(OH)m can be cyclic or acyclic.

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

[0108] The non-hydroxylated dicarboxylic acids are in particular chosen from maleic acid, propanedioic acid, butanedioic acid, pentanedioic acid, hexanedioic acid, decanedioic acid, dodecanedioic acid, cyclo-propanedicarboxylic acid, cyclohexanedicarboxylic acid, cyclobutanedicar-boxylic 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, tetrahydrophthalic acid, isophthalic acid, tetrahydrophthalic acid, hexahydrophthalic acid, pimelic acid, sebacic acid, azelaic acid, glutaric acid, adipic acid, fumaric acid, itaconic acid, and preferably propa- nedioic acid, butanedioic acid and pentanedioic acid.

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

[0110] The (hydroxy)tricarboxylic acids are in particular chosen 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, preferably citric acid and acotinic acid. [YES] The tetracarboxylic acids are in particular chosen from 1,2,3,4-butane-tetracarboxylic acid, pyromellitic acid, oxydisuccinic acid, thiodisuccinic acid, N[1,2-dicarboxyethyl]-L-aspartic acid, ethylenediamine tetraacetic acid, ethylenediamine tetrapropionic acid and N,N'-ethylene di-(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] HO-AK'2 fatty alcohols can be mono or polyunsaturated (presence of one or more ethylenic double bonds).

[0114] HO-AK'2 fatty alcohols can contain several alcohol functions.

[0115] Monounsaturated fatty alcohols are notably chosen from oleyl alcohol, docosenol, unsaturated fatty alcohol ethers, such as polyoxyethylene monooleyl ether, preferably oleyl alcohol. Unsaturated monounsaturated fatty alcohols containing several alcohol functions are in particular chosen from 9-Octadecene-1,12-diol.

[0116] The polyunsaturated fatty alcohols are notably chosen 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).

[0117] According to a preferred embodiment, the fatty alcohol HO-AK'2 is chosen from oleyl, linoleic alcohol (Linoleyl alcohol) or their mixtures.

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

[0119] - In a second step, all or part of the unsaturation(s) of the radical(s) AK'2 are transformed a) via an epoxidation reaction into epoxide to lead to derivatives (III'), such as compound a4 illustrated in the diagram below, or b) via a thiol-ene reaction with a (poly)hydroxylated thiol or a thiol carrying acid function(s) to lead to derivatives (IV'), such as compound b5 illustrated in the diagram below.

[0120] - 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 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 C1-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.

[0121] - 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' used in the first step are transformed into radicals -OC(O)-C(Ra)(Rb)-C(O)-R4, for example via a transesterification reaction with an ester Gp-C(O)-C(Ra)(Rb)-C(O)-R4 in which Gp preferably denotes a hindered alkoxy radical such as tBu-O- to lead to the corresponding compounds of formula (I).

[0122] Compounds of formula (la) to (le) such that p is equal to 1, Y denotes -C(O)-O- and m is equal to 1 can 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] As an example, the reaction scheme below can be implemented in which all the epoxides are opened by methanol and then each hydroxy is esterified by t-Bu-OCOCH2CH3: Coinposé a4 Compound b4 Compound b4 Compound c4

[0124] As an example, the reaction scheme below can be implemented in which an unsaturated oil reacts with a (poly)hydroxy thiol such as SH-(CH2)X OH, with x being an integer preferably from 1 to 4, then a transesterification reaction (as described in Desroches, M., Caillol, S., Lapinte, V., Auvergne, R., & Boutevin, B. (2011). Synthesis of biobased polyols by thiol-ene coupling from vegetable oils. Macromolecules, 44(8), 2489-2500): Compound Compound c5

[0125] As an example, the reaction scheme below can be implemented in which all the epoxides are opened by lactic acid and then each hydroxy is esterified by t-Bu-OCOCH2CH3: Compound a6 Compound b6 Compound b6 Compound c6 (Poly)amino compounds

[0126] The (poly)amine compound(s) may in particular be chosen from polyamine compounds having several primary amine 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, in particular 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 by one or more heteroatoms or groups chosen from -O-, -S-, -Si(R')2-, -N(R”)-, preferably -O-, -Si(R')2-, or combinations thereof such as -Si(R')2-O- or -O-Si(R')2-, with R', identical or different, representing a (Ci-C4)alkyl group such as methyl, and R” representing a hydrogen atom or a (Ci-C4)alkyl group, preferably a hydrogen atom.

[0128] By "non-polymeric compound" is meant a compound which is not directly obtained by a polymerization reaction of monomers.

[0129] As (poly)amino compounds, mention may in particular be made of 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, l,2-bis(3-aminopropylamino)ethane, N,N'-bis(3-aminopropyl)-l,3-propanediamine, ethylene diamine, 1,3-propylenediamine, 1,4-butylenediamine, lysine, cystamine, xylene diamine, tris(2-aminoethyl)amine, l,3-bis(aminomethyl)cyclohexane, l,4-bis(aminomethyl)cyclohexane, diaminopropanol, 4,7,10-Trioxa-l,13-tridecanediamine, spermidine and C36-alkylenediamines (respectively Priamine™ 1071, 1073, 1074, 1075), 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, namely they contain a single primary and / or secondary amine group, preferably primary (NH2).

[0131] The (poly)amine compound(s) may be chosen from amino alkoxysilanes, in particular of formula R'iSi(OR'2)z(R'3)x in which: - R'i is a linear or branched, saturated or unsaturated, cyclic or acyclic C1-C6 hydrocarbon chain substituted by a group chosen from the primary NH2 or secondary -N(H)R amine groups with R representing a C1-C4 alkyl, an aryl, a benzyl substituted by an amino group or by a C1-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, identical or different, represent a linear or branched (Ci-C6)alkyl group, - z denotes an integer from 1 to 3, and - x denotes an integer from 0 to 2, with z + x = 3.

[0132] In particular, R\ is an acyclic chain. Preferably, R\ is a linear or branched, saturated or unsaturated, C1-C6 hydrocarbon chain substituted by an amine group -NH2 or -N(H)R, with R representing a C1-C6 alkyl, a C3-C6 cycloalkyl or C6 aromatic. More preferably, R' 1 is a linear, saturated C1-C6 hydrocarbon chain substituted by an amine group NH2. Even more preferably, R' 1 is a linear saturated C2-C4 hydrocarbon chain substituted by an NH2 amine group.

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

[0134] 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 group or ethyl. Preferably, z is equal to 3.

[0135] In particular, the (poly)amine compound(s) are chosen from amino alkoxysilanes comprising 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.

[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 preferably 3-aminopropyl triethoxysilane (APTES), in particular that marketed by Sigma Aldrich.

[0137] The (poly)amine compound(s) may also be chosen from amino polymers, in particular having a weight-average molecular weight ranging from 500 g.mol1 to 1,000,000 g.mol *, preferably ranging from 500 g.mol1 to 500,000 g.mol *, and preferentially ranging from 500 g.mol1 to 100,000 g.mol *.

[0138] According to a particular embodiment of the invention, the (poly)amine compound(s) are monoamine and chosen from polydialkylsiloxanes, in particular of formula (IV): H2N-ALK-Si(R'2)(R'3)-O-[ Si(R'2)(R'3)-O]n- Si(R'2)(R'3)-R'4(IV) formula (IV) in which: - ALK represents a linear or branched (Ci-C4)alkylene group, preferably linear, such as propylene, - R'2, and R'3, 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 C4, such as n-butyl, ne 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 *. As an example of polydimethylsiloxanes (IV), mention may be made of those 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 compound(s) are diamined, namely they contain two primary and / or secondary amine groups, preferably primary (NH2).

[0140] More particularly, they are chosen from the compounds of formulas (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', identical or different, represent a (Ci-C6)alkylene group, linear or branched, preferably linear, such as propylene, - R', identical or different, represents a (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 weight average molecular weight of the compound (V) or (VI) ranges from 500 g.mol1 to 55000 g.molA

[0141] 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.

[0142] The (poly)amine compound(s) which are diamined are particularly the diamined polyethers, in particular of formula H2N-ALK-O-[ALK'-O]m-ALK”-NH2 with ALK, ALK' and ALK”, which are identical or different, representing a linear or branched (Ci-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 polyethylene glycol and / or polypropylene glycol a, co-diamine (with an 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.

[0143] According to a particular embodiment of the invention, the (poly)amine compound(s) are triaminated, namely they contain three primary and / or secondary amine groups, preferably primary (NH2). More particularly, they are chosen from triaminated polyethers, in particular 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.

[0144] As (poly)amine compounds which are triaminated, triaminated polyethers are particularly cited, such as those sold under the name Jeffamine T-403.

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

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

[0147] Preferably, the (poly)amine 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.

[0148] According to this variant, the (poly)amine compound(s) are in particular chosen from poly(alkylene (C2-C5)imines), and preferably polyethyleneimines and polypropyleneimines, in particular poly(ethyleneimine), in particular that sold under the reference 408700 by the company Aldrich Chemical or under the trade name Lupasol by BASF, in particular with a molecular weight of between 1,200 and 25,000; poly(allylamine), in particular that sold under the reference 479136 by the company Aldrich Chemical; polyvinylamines and their copolymers, in particular with vinylamides, in particular vinylamine / vinylformamide copolymers such as those sold under the name Lupamin® 9030 by the company BASF; polyamino acids having NH2 groups such as polylysine, in particular that sold by the company JNC Corporation (formerly Chisso); amino dextran, in particular that sold by the company CarboMer Inc;polyvinyl amino alcohol, in particular that sold by the company CarboMer Inc, copolymers based on acrylamido(Ci-C6)alkylamine, in particular based on acrylamidopropylamine; 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 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 hydroxy or (Ci-C4)alkyl group, - Rb and Rc, identical or different, preferably identical, represent a (Ci-C4)alkyl group, such as methyl, - ALK1 represents a linear or branched (Ci-C6)alkylene group, optionally interrupted by an N(H) group, - m and n are integers greater than or equal to 1, preferably m and n are such that the weight-average molecular mass of the compound of formula (VII) ranges from 1000 g.mol1 to 500000 g.mol *.

[0150] According to a preferred variant, the formula (VII) is such that Ra, Rb, and Rc represent a methyl group, ALK1 represents a propylene group, n and m are such that the values ​​of n and m are such that the weight average molecular weight of the polydimethylsiloxane ranges from 1000 g.mol1 to 55000 g.mol *.

[0151] 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.

[0152] 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) group )alkylene 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.mol *.

[0153] As amino polymers, polytetrahydrofuran (or polytetramethylene glycol) a, co-diamine, and polybutadienes a, co-diamine may also be cited.

[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 carrying at least one amino group, such as polyamidoamine PAMAM 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 comprising 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 a, co-diamine, with an amine function at the end of the chain, (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-C20 hydrocarbon chain, optionally interrupted by one or more heteroatoms chosen from -O-, -N(R)- with R denoting a hydrogen atom or a C1-C4 alkyl radical, in particular spermidine and 4,7,10-Trioxa-1,13-tridecanediamine, and if) polydialkylsiloxanes comprising primary amine groups at the end of the chain or on side chains, in particular polidimethylsiloxanes 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.

[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 preferably ranging from 0.1% to 3% by weight, even more preferably ranging from 0.1% to 2% by weight, relative to the total weight of composition (C).

[0158] When composition (C) further 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 preferably ranging from 0.1% to 3% by weight, even more preferably 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. which comprises a cosmetically acceptable medium, i.e. a medium compatible with human keratin fibers.

[0160] When present, composition (B) is a cosmetic composition, i.e. which comprises a cosmetically acceptable medium, i.e. a medium 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 having from 2 to 6 carbon atoms, more preferably chosen from ethanol, propanol, n-butanol, isopropanol, isobutanol, tert-butanol, pentanol, hexanol, and mixtures thereof, even more preferably chosen from n-butanol, ethanol, and mixtures thereof, most preferably ethanol.

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

[0163] According to a particular embodiment, the composition (C) comprises one or more oils distinct from the compounds A, preferably chosen from hydrocarbon oils, more preferably chosen from C8-Ci6 hydrocarbon oils, even more preferably chosen from iso-alkanes, and better chosen from C13-Ci6 iso-paraffins, isododecane, isohexadecane, and mixtures thereof, and even better isododecane.

[0164] By "oil" is meant a non-aqueous compound, immiscible with water, liquid at room temperature (20°C) and atmospheric pressure (760 mm Hg).

[0165] By "hydrocarbon oil" is meant an oil formed essentially, or even consisting of, carbon and hydrogen atoms, and possibly oxygen and nitrogen atoms, and not containing silicon or fluorine atoms. It may contain alcohol, ester, ether, carboxylic acid, amine and / or amide groups.

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

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

[0168] The term "anhydrous composition" means a composition comprising a quantity of less than 5% by weight of water, preferably less than 3% by weight of water, more preferably less than 1% by weight of water, relative to the total weight of the composition. position in question, and better the composition considered is free of water. Where appropriate, such small quantities of water may in particular be brought by ingredients of the composition which may contain residual quantities of it.

[0169] Composition (C) may be presented in all the galenic forms conventionally used for hair application. In a non-limiting manner, composition (C) may be presented in the form of a lotion, a cream, a mousse, a gel, a spray or a lacquer.

[0170] Preferably, composition (C) is used in a leave-in 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 or mixed before application to a mask or a conditioning composition.

[0172] Composition (C) may be packaged in a pump bottle or in an aerosol container, in order to ensure application of composition (C) in spray form (lacquer) or in foam form. In these cases, composition (C) preferably comprises at least one propellant.

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

[0174] By "coloring agent" is meant an oxidation dye, a direct dye or a pigment.

[0175] By "oxidation dye" is meant an oxidation dye precursor chosen from oxidation bases and couplers. Oxidation bases and couplers are compounds with little or no color which, by a condensation reaction in the presence of an oxidizing agent, give a colored species.

[0176] By "direct dye" is meant a natural and / or synthetic dye, including in the form of extract(s), different from oxidation dyes. These are colored compounds which will diffuse superficially on the fiber. They can be ionic or non-ionic, i.e. anionic, cationic, neutral or non-ionic.

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

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

[0179] By "cationic polymer" is meant any non-silicone polymer (not comprising a silicon atom) containing cationic groups and / or groups ionizable into cationic groups, and not containing anionic groups and / or groups ionizable into anionic groups. Examples

[0180] The following examples allow a better understanding of the invention without, however, being limiting in nature.

[0181] Example A: Synthesis of castor oil with acetoacetate function (Compound No. 1)

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

[0183] In a 250 mL SVL® reactor equipped with mechanical stirring, a thermometer and a distillation column, 50 g of castor oil (marketed by Société Interchimie) and 25.40 g of tert-butyl acetoacetate are introduced. The reaction medium is heated to 130 °C using an oil bath. After 7 hours, the reaction medium is cooled, introduced into a 250 mL bulb flask, and heated to 120 °C under continuous vacuum in a rotavapor for 1 hour. A slightly yellow oil is obtained.

[0184] Examples 1 to 5: Examples of application on wicks

[0185] The following compositions were prepared from the contents indicated in the tables below. The contents are expressed as a percentage by weight, relative to the total weight of the composition considered. Compositions Al and A2

[0186] [Tables 1] Ingredients A1 (Invention) A2 (Comparative) Compound No. 1 of example A 0.5 Castor oil marketed by Interchimie - 0.5 Ethanol Qsp 100 Qsp 100 Composition B

[0187] [Tables2] Ingredients B Jeffamine T403 Polyetheramine (Mw=440g / mol) AHEW (81 g / eq) 0.25 Ethanol Qsp 100 Reference composition RI

[0188] [Tables 3] Ingredients RI Ethanol Qsp 100 Application and evaluation protocol

[0189] Five strands of 2.7 g type IV hair were pre-washed with shampoo.

[0190] Composition Al was applied to a first strand according to a bath ratio of 0.5 g of composition Al to 1 g of hair.

[0191] Composition A2 was applied to a second strand according to a bath ratio of 0.5 g of composition Al to 1 g of hair.

[0192] A composition Cl was prepared by mixing 1 part by weight of composition Al with 1 part by weight of composition B and then applied to a third strand according to a bath ratio of 1g of composition Cl to 1g of hair.

[0193] 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 strand according to a bath ratio of 1g of composition Cl to 1g of hair.

[0194] The fifth strand is a control strand to which only the reference composition RI was applied according to a bath ratio of 1g of reference composition RI to 1g of hair.

[0195] The different compositions are applied to damp hair placed flat on aluminum foil. After applying the compositions, the strands are wrung out with the fingers, dried on KIMTECH absorbent paper and then hung in the open air until completely dry. The strands are then placed suspended in an oven at 60°C for 20 minutes and then in an oven at 25°C and 80% relative humidity for 24 hours.

[0196] Monitoring of the evolution of frizz and volume is carried out using a device designed by the company Bossa Nova, called BOLERO LITE with a measurement at T0 after treatment with the composition, drying 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.

[0197] The BOLERO LITE is a 2D image capture and analysis system dedicated to quickly and efficiently discriminating on a strand of hair, the fibers corresponding to the frizz from those forming part of the body of the strand. By using uniform backlighting, it is possible to measure the variations in light transmission through the hair sample with a standard black and white image and therefore evaluate the hair density. For each pixel of the image, we measure the transmitted light.

[0198] If the transmission:

[0199] ■ is lower than a defined threshold, this corresponds to a high density area and we we can define the pixel as part of the body / volume of the strand;

[0200] ■ is greater than the defined threshold, it is a low density area and we can set the pixel as part of the fly-away / frizz;

[0201] ■ is above the sensitivity threshold, it is estimated that the perceived signal corresponds to noise. It is therefore not taken into account.

[0202] In the context of our study, the defined threshold is set at 50% and the sensitivity threshold is set at 95%.

[0203] The BOLERO LITE image analysis software allows obtaining the value of the body surface area and the frizz surface area (in cm2) of each of the strands tested. Evaluation results

[0204] The results of the frizz surface measurements (in cm2) are summarized in the table below:

[0205] [Tables4] Examples Composition tested Frizz surface at T0 (in cm2) Frizz surface at T0 + 24H 80% RH (in cm2) 1 (Invention) Al 19.519 33.649 2 (Comparative) A2 12.619 42.548 3 (Invention) Cl 11.53 23.567 4 (Comparative) C2 10.77 83.882 5 (Control) RI 52.9 67.7

[0206] The use of the compounds according to the invention makes it possible to limit the formation of frizz and the increase in the volume of the hair in a humid environment.

Claims

Claims

1. 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) to protect keratin fibers from humidity, preferably to limit the formation of frizz and / or the increase in volume of the hair in a humid environment, the compound(s) A being chosen from the compounds of formula (I), their optical and geometric isomers, their solvates such as hydrates, and their mixtures: (I) (H)p - Z.......(Y-AOja [(O)r(AKl) q -^ formula (I) in which: - Z represents a multivalent hydrocarbon radical from C2 to C40, in particular from 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 combinations thereof; - AK1 represents a linear or branched divalent hydrocarbon chain saturated or unsaturated in C1-C12, preferably in C1-C6, more preferably saturated in C1-C6; - AK2 represents a linear or branched, saturated or unsaturated, monovalent hydrocarbon chain, 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 combinations thereof, 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 C1-C6, more preferably saturated in C1-C6, even more preferably in C1-C4; - R represents a hydrogen atom, a linear or branched saturated or unsaturated C1-C6, preferably C1-C4, alkyl radical, in particular methyl, or a radical -C(O)-C(Ra)(Rb)-C(O)-R4;

2. - X represents -O-, -S-, -OC(O)- or -C(O)-O-; - Y represents -OC(O)- or -C(O)-O-; - R4 represents a monovalent C1 to C6 hydrocarbon radical, linear or branched, saturated or unsaturated, preferably a (C1-C4)alkyl group, in particular methyl or tert-butyl, more preferably methyl; - Ra and Rb, identical or different, represent a hydrogen atom or a (CrC4)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(R a)(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. Use according to claim 1, in which the compound(s) A are chosen from the compounds of formula (I), their optical and geometric isomers, their solvates such as hydrates, and their mixtures, formula (I) in which: - 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, monovalent hydrocarbon chain, C[2-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 combinations thereof, in particular -O(CO)- or -C(O)-O-; - Y, AK3, v, R, X, R4, Ra and Rb being as defined in claim 1; it being understood that the compounds of formula (I) contain at least 2 radicals -C(O)-C(Ra)(Rb)-C(O)-R4.

3. Use according to any one of the preceding claims, in which the compound(s) A are chosen from the following compounds (1), (2), (3), (4), (7), (8), (9), (11) and (16), their optical and geometric isomers, their solvates such as hydrates, and their mixtures: (2)

4.

5.

6.

7. preferably among compounds (4), their optical, geometric isomers, their solvates such as hydrates, and their mixtures. Use according to 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 preferably ranging from 0.1% to 2% by weight, relative to the total weight of the composition (C). Use according to any one of claims 1 to 3, in which the compound(s) A are used in combination with one or more (poly)amine compounds, the (poly)amine compound(s) preferably being applied to the keratin fibres before, after or at the same time as the compound(s) A. Use according to any one of claims 1 to 4, in which the composition (C) comprises the compound(s) A and one or more (poly)amine compounds. Use according to claim 5 or 6, in which the (poly)amine compound(s) are chosen from: ia) (poly)amine compounds comprising 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 a, co-diamine, with an amine function at the chain end, ic) polyether triamines, id) aminoalkoxysilanes, in particular APTES, (ie) NH2-alk-NH2 polyamine compounds, in which alk denotes a divalent C2-C20 hydrocarbon chain, optionally interrupted by one or more heteroatoms chosen from -0-, -N(R)- with R denoting a hydrogen atom or a C1-C4 alkyl radical, in particular spermidine and 4,7,10-Trioxa-1,13-tridecanediamine, and if) 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, more particularly bis-cetearyl amodimethicone; preferably from ic) polyether triamines.

8. Use according to claim 6 or 7, in which the 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 preferably ranging from 0.1% to 2% by weight, relative to the total weight of the composition (C).

9. Use according to any one of claims 1 to 4 or 6 to 8, in which the composition (C) comprises one or more polar and / or protic solvents, preferably chosen from monoalcohols having from 2 to 6 carbon atoms, more preferably chosen from ethanol, propanol, n-butanol, isopropanol, isobutanol, tert-butanol, pentanol, hexanol, and mixtures thereof, even more preferably chosen from n-butanol, ethanol, and mixtures thereof, most preferably ethanol.

10. Use according to the preceding claim, in which the 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 the composition (C).

11. Use according to any one of claims 1 to 4 or 6 to 10, wherein composition (C) is an anhydrous composition.

12. Use according to any one of claims 6 to 11, in which the 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).