Composition in the form of a direct emulsion comprising at least one compound with acetoacetate functions, at least one fatty acid and at least chitosan
A direct oil-in-water emulsion composition with acetoacetate functions, fatty acids, chitosan, and optional pigments addresses the issue of short-lasting hair color by providing a stable, water-resistant, and long-lasting coloring solution with improved environmental and natural ingredient credentials.
Patent Information
- Application Number
- FR2023012927
- Authority / Receiving Office
- FR · FR
- Patent Type
- Applications
- Current Assignee / Owner
- Filing Date
- 2023-11-23
- Publication Date
- 2025-05-30
- Estimated Expiration
- 2043-11-23
AI Technical Summary
Existing hair coloring methods, particularly those using pigments, suffer from low resistance to water, shampoos, and external aggressions, leading to short-lasting color results.
A composition in the form of a direct oil-in-water emulsion containing at least one compound with acetoacetate functions, fatty acids, chitosan, and optionally pigments, which forms a stable, non-sticky coating resistant to water and shampoos.
The composition provides a long-lasting, water-resistant hair coloring that minimizes transfer and discomfort, while also offering improved carbon footprint and natural origin ingredients.
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Abstract
Description
Title of the invention: Composition in the form of a direct emulsion comprising at least one compound with acetoacetate functions, at least one fatty acid and at least chitosan
[0001] The present invention relates to a composition in the form of a direct oil-in-water (O / W) emulsion comprising at least one compound of formula (I), as defined below, at least one fatty acid, at least one chitosan, and optionally at least one pigment.
[0002] The present invention also relates to a method for the cosmetic treatment, preferably for coloring, of keratin fibers, in particular human keratin fibers such as hair, comprising at least the application to said fibers of at least one composition as defined above.
[0003] In the field of coloring hair keratin fibers, it is already known to color hair keratin fibers using different techniques using direct dyes or pigments for non-permanent colorings or dye precursors for permanent colorings.
[0004] There are basically three types of hair coloring process:
[0005] a) so-called permanent coloring which has the function of bringing about a significant modification of the natural color and which uses oxidation dyes which penetrate into the hair fiber and form the dye by a process of oxidative condensation;
[0006] b) non-permanent, semi-permanent or direct coloring, which does not involve the oxidative condensation process and is resistant to 4 or 5 shampoos; consists of dyeing keratin fibers with dyeing compositions containing direct dyes;
[0007] c) temporary coloring which results in a change in the natural color of the hair which lasts from one shampoo to the next and which serves to enhance or correct a shade already obtained. It can also be likened to a “make-up” process.
[0008] Another coloring method consists of using pigments. Indeed, the use of pigments on the surface of keratin fibers generally makes it possible to obtain visible colorings on dark hair since the pigment on the surface masks the natural color of the fiber. However, the colorings obtained by this coloring method still have the disadvantage of having low resistance to water and shampoos as well as to external agents such as brushing and / or rubbing.
[0009] Thus there is a real need to propose compositions intended for the treatment cosmetic, preferably for coloring, keratin fibers, in particular human keratin fibers, in particular human keratin fibers such as hair, not having the drawbacks mentioned above, that is to say stable compositions capable of leading to a non-sticky coating, transferring little, if at all, and resistant to external aggressions, in particular water and / or shampoos, guaranteeing in particular good resistance of the coloring over time.
[0010] Furthermore, in this context, it is important to develop new compositions having a better carbon footprint, in particular by promoting the use of renewable raw materials and / or with a good index of naturalness and / or of natural origin and more particularly of plant origin while reducing the use of compounds of petrochemical origin.
[0011] The present invention therefore relates in particular to a composition in the form of an oil-in-water emulsion, comprising: - i) one or more compounds of formula (I), as well as its optical, geometric and / or solvated isomers, such as hydrates: (I) [(O)r(AKl)< r (O^
[0012] formula (I) in which:
[0013] - Z represents a multivalent hydrocarbon radical in C2 to C40, in particular in C3 to C36, linear or branched, saturated or unsaturated, conjugated or not, acyclic or cyclic, aromatic or not, Z possibly being interrupted by one or more groups or heteroatoms chosen from -O-, -N(Ra)-, -S-, -C(O)-, (hetero)cycles, and combinations thereof;
[0014] - AK1 represents a saturated linear or branched divalent hydrocarbon chain or unsaturated in C1-C12, preferably in C1-C6, more preferably saturated in C1-C6;
[0015] - AK2 represents a linear or branched monovalent hydrocarbon chain, saturated or unsaturated, 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-;
[0016] - AK3 represents a saturated linear or branched divalent hydrocarbon chain or unsaturated in C1-C12, preferably in C1-C6, more preferably saturated in C1-C6, even more preferably in C1-C4;
[0017] - R represents a hydrogen atom, a saturated linear or branched alkyl radical or unsaturated in C1-C6, preferably in C1-C4, in particular methyl, or a radical -C(O)-C(Ra)(Rb)-C(O)-R4;
[0018] - X represents -O-, -S-, -OC(O)- or -C(O)-O-;
[0019] - Y represents -OC(O)- or -C(O)-O-;
[0020] - R4 represents a monovalent C1 to C6 hydrocarbon radical, linear or branched, saturated or unsaturated, preferably a (Ci-C4)alkyl group, in particular methyl or tert-butyl, more preferably methyl;
[0021] - Ra and Rb, identical or different, represent a hydrogen atom or a group (CrC4)alkyl, preferably a hydrogen atom;
[0022] - p denotes an integer equal to 0 or 1;
[0023] - 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;
[0024] - n denotes an integer equal to 0, 1, 2, 3 or 4; it being understood that when n is greater than 1, then the radicals -(O)t-(AKi)q-(OC(O)-C(Ra)(Rb)-C(O)-R4)u are identical or different;
[0025] -1 denotes an integer equal to 0 or 1;
[0026] - q denotes an integer equal to 0 or 1;
[0027] - u denotes an integer equal to 1, 2 or 3;
[0028] - v denotes an integer equal to 1, 2 or 3;
[0029] 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;
[0030] ii) one or more fatty acids,
[0031] iii) at least one chitosan, and iv) optionally one or more pigments,
[0032] v) optionally one or more fatty substances different from the fatty acid(s) ii).
[0033] The composition according to the invention makes it possible to achieve the objectives as described above. cedly, that is to say that the composition is a stable oil-in-water (O / W) emulsion which leads to a non-sticky coating resistant to external aggressions, for example, water, and / or shampoos, in order to treat keratin fibers, in particular human keratin fibers such as hair.
[0034] In other words, the application of the composition according to the invention makes it possible to provide deposits on the keratin fibers having good resistance to external aggressions, such as water, shampoos, and therefore having very good resistance over time.
[0035] The deposits or coatings thus formed on the keratin fibers do not stick and transfer little, if at all, which makes it possible to minimize problems of discomfort after application.
[0036] The composition according to the invention also has the advantage of being an oil-in-water (O / W) emulsion which is stable at room temperature, in particular at a temperature of 20°C.
[0037] By "stable" is meant, within the meaning of the present invention, that 1) the formulation process gives rise to a direct emulsion without the presence of phase separation (creaming or sedimentation) and / or aggregates and 2) that the visual and microscopic appearance, the viscosity and / or the pH of the composition in the form of an oil-in-water emulsion does not change or changes little during a storage period, in particular at least one week at room temperature.
[0038] For the purposes of the present invention, ambient temperature means a temperature of 20°C.
[0039] The composition according to the invention has in particular a creamy texture and a white to yellowish appearance which is stable over time (at least 1 week) at room temperature, in particular at a temperature of 20°C.
[0040] Advantageously, when the composition according to the invention comprises at least one pigment, and is applied to keratin fibers, in particular to human keratin fibers such as hair, it leads to a coloring resistant to external aggressions, preferably to a coloring that is permanent in water and / or shampoos.
[0041] The composition according to the invention thus makes it possible to improve the color retention of colored keratin fibers, in particular of a coloring induced by at least one pigment, in particular with regard to the use of one or more shampoos, in particular several shampoos.
[0042] Furthermore, the emulsification of the composition according to the invention leads in particular to an improvement in the persistence of the coloring, in particular of keratin fibers, preferably compared to water and / or shampoos.
[0043] Furthermore, the composition may further comprise glycerin, which leads to an improvement in the color retention on keratin materials, in particular on keratin fibers, preferably human keratin fibers such as hair.
[0044] The composition according to the invention can thus be applied to keratin fibers, in particular for coloring keratin fibers.
[0045] The composition according to the invention also has an improved carbon footprint.
[0046] The invention thus relates to a process for the cosmetic treatment of keratin fibers, in particular human keratin fibers such as hair, comprising at least the application to said fibers of at least one composition, in the form of an oil-in-water emulsion, comprising at least one compound of formula (I), as defined above, its optical, geometric and / or solvated, such as hydrates, at least one fatty acid and at least one chitosan.
[0047] Preferably, the treatment method is a method for coloring keratin fibers, in particular human keratin fibers, such as hair, comprising at least the application to said fibers of at least one composition, in the form of an oil-in-water emulsion, comprising at least one compound of formula (I), as defined above, its optical, geometric and / or solvated isomers, such as hydrates, at least one fatty acid, at least one chitosan, and at least one pigment.
[0048] The invention also relates to the use of said composition for the treatment, preferably the coloring, of keratin fibers, in particular human keratin fibers, such as hair.
[0049] Other objects, characteristics, aspects and advantages of the invention will appear even more clearly on reading the description and the example which follows.
[0050] In what follows, and unless otherwise indicated, the limits of a domain of values are included in this domain, in particular in the expressions “between” and “ranging from ... to ...”.
[0051] Furthermore, the expression “at least one” used in the present description is equivalent to the expression “one or more”.
[0052] Similarly, the expression "at least" used in the present description is equivalent to the expression "greater than or equal to".
[0053] Furthermore, the expression "coloring agent" used in the present description is equivalent to the expression "coloring agent".
[0054] In a manner known per se, the term “Cn” or “Cn” compound or group denotes a compound or group containing “n” carbon atoms in its chemical structure.
[0055] For the purposes of the present invention, and unless otherwise indicated:
[0056] By “(hetero)aryl” is meant aryl or heteroaryl groups.
[0057] By “(hetero)cycloalkyl” is meant cycloalkyl or heterocycloalkyl groups.
[0058] The radicals “aryl” or “heteroaryl” or the aryl or heteroaryl part of a radical may be substituted by at least one substituent carried by a carbon atom, chosen from: - a C1-C6 (poly)(hydroxy)alkyl radical, preferably 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 C1-C4 alkyl radical and the radical R' is a C1-C4 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 CrC4 alkyl radical and the radical R' represents a CrC4 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).
[0059] The cyclic or heterocyclic part of a non-aromatic radical may be substituted by at least one substituent carried by a carbon atom chosen from the groups: • hydroxy, • C2-C4 alkoxy, (poly)hydroxyalkoxy C2-C4, • alkylcarbonylamino ((RC(O)-NR'-) in which the radical R' is an atom hydrogen, a CrC4 alkyl radical and the radical R is a CrC2 alkyl radical, amino substituted by one or two identical or different CrC4 alkyl groups; • alkylcarbonyloxy ((RC(O)-O-) in which the radical R is an alkyl radical in CrC4, amino substituted by one or two identical or different alkyl groups in CrC4; • alkoxycarbonyl ((ROC(O)-) in which the radical R is a CrC4 alkyl radical, amino substituted by one or two identical or different CrC4 alkyl groups;
[0060] - A cyclic, heterocyclic radical, or a non-aromatic part of a radical aryl or heteroaryl, may also be substituted by one or more oxo groups.
[0061] - A hydrocarbon chain is unsaturated when it contains one or more double bonds and / or one or more triple bonds.
[0062] - An “aryl” radical represents a mono or polycyclic group hy carbon radical, 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.
[0063] - 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; preferentially a heteroaryl radical is chosen from acridinyl, benzimidazolyl, benzobistriazolyl, benzopyrazolyl, benzopyridazinyl, benzoquinolyl, benzothiazolyl, benzotriazolyl, benzoxazolyl, pyridinyl, tetrazolyl, dihydrothiazolyl, imidazopyridinyl, imidazolyl, indolyl, isoquinolyl, naphthoimidazolyl, naphthooxazolyl, naphthopyrazolyl, oxadiazolyl, oxazolyl, oxazolopyridyl, phenazinyl, phenoxazolyl, pyrazinyl, pyrazolyl, pyrilyl, pyrazoyltriazyl, pyridyl, pyridinoimidazolyl, pyrrolyl, quinolyl, tetrazolyl, thiadiazolyl, thiazolyl, thiazolopyridinyl, thiazoylimidazolyl, thiopyrylyl, triazolyl, xanthylyl.
[0064] - 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.
[0065] - A “heterocyclic” or “heterocycloalkyl” radical is a non-cyclic radical mono or polycyclic aromatic, condensed or not, containing from 3 to 9 links, 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.
[0066] - An “alkyl” radical is a saturated, linear or branched hydrocarbon radical, in particular particularly in C1-C6, preferably in C1-C4.
[0067] - 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.
[0068] - 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. A. Composition in the form of an oil-in-water emulsion
[0069] As indicated above, the composition according to the invention is an oil-in-water (O / W) emulsion.
[0070] The composition according to the invention thus comprises a fatty phase and an aqueous phase, in particular a dispersed fatty phase and a continuous aqueous phase.
[0071] The composition according to the invention comprises in particular an aqueous phase comprising at least one chitosan and at least one fatty acid as defined below.
[0072] Preferably, the weight ratio between the fatty phase and the aqueous phase varies from 0.001 to 6, preferably from 0.01 to 1, more preferably varies from 0.05 to 0.3.
[0073] Al Aqueous phase
[0074] The aqueous phase is contained in the composition according to the invention preferably in an amount ranging from 40 to 99% by weight, preferably in an amount ranging from 80 to 99% by weight, relative to the total weight of the composition.
[0075] The aqueous phase comprises in particular water, at least one chitosan and at least one acid, organic or mineral, preferably organic.
[0076] According to a preferred embodiment, the aqueous phase comprises at least one organic acid having a pKa of less than 5, as defined below.
[0077] The aqueous phase preferably comprises water, at least one chitosan, and at least one acid, organic or mineral, preferably organic and having a pKa of less than 5, as defined below.
[0078] The aqueous phase preferably has a pH less than or equal to 6, better still a pH ranging from 4 to 5.5.
[0079] Preferably, the aqueous phase is present in an amount ranging from 40 to 99% by weight, better still in an amount ranging from 80 to 99% by weight, relative to the total weight of the composition, and comprises water, at least one chitosan, and at least one acid, organic or mineral, preferably organic and having a pKa of less than 5.
[0080] Preferably, the aqueous phase comprises water in a content ranging from 70 to 99% by weight, at least one chitosan, in a content ranging from 0.5 to 15% by weight, and at least one acid, preferably at least one C1-C6 carboxylic acid of formula (Q), as defined below and having a pKa of less than 5 in a content ranging from 0.5 to 15% by weight, relative to the total weight of the aqueous phase.
[0081] According to a preferred embodiment, the composition according to the invention comprises:
[0082] - preferably a content ranging from 40 to 99% by weight, more preferably a content ranging from 80 to 99% by weight, relative to the total ratio of said composition, of an aqueous phase comprising: - water in a content ranging from 70 to 99% by weight, relative to the total weight of the aqueous phase, - at least one chitosan, in a content ranging from 0.5 to 15% by weight, relative to the total weight of the aqueous phase, and - at least one organic acid, preferably at least one C1-C6 carboxylic acid of formula (Q), as defined below and having a pKa of less than 5 in a content ranging from 0.5 to 15% by weight, relative to the total weight of the aqueous phase. Chitosan
[0083] The composition according to the invention contains iii) at least one chitosan.
[0084] Preferably, the chitosan is chosen from poly(D-glucosamines).
[0085] Preferably, the degree of acetylation of the chitosan is less than or equal to 30%, more preferably less than or equal to 15% and even more preferably varies from 1 at 10%.
[0086] Chitosan may be present in the aqueous phase in a content ranging from 0.5 to 15% by weight, better still in a content ranging from 0.5 to 10% by weight, relative to the total weight of the aqueous phase.
[0087] Chitosan may be present in the composition according to the invention in a content ranging from 0.5 to 10% by weight, preferably in a content ranging from 2 to 6% by weight, relative to the total weight of the composition. Acid having a pKa less than 5
[0088] As indicated above, the aqueous phase comprises one or more acids having a pKa of less than 5.
[0089] The acid(s) having a pKa of less than 5 is or are preferably organic acids.
[0090] The acid(s) having a pKa of less than 5 is or are preferably C1-6 carboxylic acids.
[0091] Preferably, the acid(s) having a pKa of less than 5 correspond(s) to the following formula (Q): in which: A represents a monovalent group when n is 0, or a polyvalent group when n is greater than or equal to 1; A represents a saturated or unsaturated, cyclic or non-cyclic, aromatic or non-aromatic hydrocarbon group, comprising from 1 to 6 carbon atoms, optionally interrupted by one or more heteroatoms, and / or substituted by one or more hydroxy groups; preferably A represents a monovalent C1-C6 alkyl or phenyl group, or a polyvalent C1-C6 saturated hydrocarbon or phenylene group, A being optionally substituted by one or more hydroxy groups; n represents an integer ranging from 0 to 10, preferably from 0 to 5, better still from 0 to 2.
[0092] More particularly, the acid or acids of formula (Q) are chosen from α-hydroxy acids, in which A represents either a phenyl group, or a saturated C1-C6, in particular C1-C4, hydrocarbon group, substituted by one or more hydroxy groups; preferably by an OH group; and n ranges from 0 to 2.
[0093] More particularly, the acid or acids with a pKa of less than 5 is or are chosen from those of formula (Q) in which: n=0 and A represents a C1-C6, in particular C2-C4, alkyl group, or a C1-C6, in particular C2-C4, alkyl group substituted by an OH group; or n=0 and A represents a phenyl group, or a phenyl group substituted by an OH group; or n = 1 or 2, and A represents a di- or trivalent C1-C6, in particular C2-C4, alkyl group, or a di- or trivalent C1-C6, in particular C2-C4, alkyl group substituted by an OH group.
[0094] Even more preferably, the acid or acids with a pKa of less than 5 is or are chosen from salicylic acid, citric acid, glutaric acid, lactic acid and mixtures thereof, better still from lactic acid or citric acid.
[0095] According to one embodiment, the aqueous phase comprises a single acid having a pKa of less than 5.
[0096] According to one embodiment, the aqueous phase comprises at least lactic acid.
[0097] Even better, the acid having a pKa less than 5 is lactic acid.
[0098] The acid(s) having a pKa of less than 5 may be present in the aqueous phase in a content ranging from 0.5 to 15% by weight, better still in a content ranging from 0.5 to 10% by weight, relative to the total weight of the aqueous phase.
[0099] The acid(s) having a pKa of less than 5 may be present in the composition according to the invention in a content ranging from 0.5 to 10% by weight, preferably in a content ranging from 2 to 6% by weight, relative to the total weight of the composition.
[0100] A2. Fatty phase
[0101] The fatty phase is contained in the composition according to the invention preferably in an amount ranging from 0.5 to 50% by weight, preferably in an amount ranging from 0.5 to 15% by weight, relative to the total weight of the composition.
[0102] For the purposes of the present invention, it is understood that the fatty phase corresponds to the oily phase of the oil-in-water emulsion. The terms “fatty phase” and “oily phase” may be used interchangeably in the description.
[0103] The fatty phase comprises in particular at least one compound of formula (I), as well as their optical, geometric and / or solvated isomers, such as hydrates, as defined below, and at least one fatty acid ii) as defined below.
[0104] Preferably, the fatty phase is present in the composition in an amount ranging from 0.5 to 50% by weight, preferably in an amount ranging from 0.5 to 15% by weight, relative to the total weight of the composition, and comprises i) at least one compound of formula (I), as well as their optical, geometric and / or solvated isomers, such as hydrates, as defined below, and ii) at least one fatty acid as defined below.
[0105] The fatty phase may further contain v) at least one fatty substance, preferably at least one oil as defined below, which is different from the fatty acid(s) ii).
[0106] According to one embodiment, the fatty phase comprises i) at least one compound of formula (I), as well as their optical, geometric and / or solvated isomers, such as hydrates, as defined below, ii) at least one fatty acid as defined below, and v) at least one fatty substance, preferably at least one oil different from the fatty acids ii).
[0107] According to a preferred embodiment, the fatty phase is present in the composition in an amount ranging from 0.5 to 50% by weight, preferably in an amount ranging from 0.5 to 15% by weight, relative to the total weight of the composition, and comprises i) at least one compound of formula (I), as well as their optical, geometric and / or solvated isomers, such as hydrates, as defined below, ii) at least one fatty acid as defined below and v) at least one fatty substance, preferably at least one oil different from the fatty acid(s) ii). Compound of formula (I):
[0108] The composition according to the invention comprises i) at least one compound of formula (I).
[0109] As indicated above, the compound(s) of formula (I), as well as their optical, geometric and / or solvated isomers, such as hydrates, is or are such that: (I) (H)p - - (Y-AK2X [(0)^0
[0110] formula (I) in which:
[0111] - Z represents a multivalent hydrocarbon radical in C2 to C40, in particular in C3 to C36, linear or branched, saturated or unsaturated, conjugated or not, acyclic or cyclic, aromatic or not, Z possibly being interrupted by one or more groups or heteroatoms chosen from -O-, -N(Ra)-, -S-, -C(O)-, (hetero)cycles, and combinations thereof;
[0112] - AK1 represents a saturated linear or branched divalent hydrocarbon chain or unsaturated in C1-C12, preferably in C1-C6, more preferably saturated in C1-C6;
[0113] - AK2 represents a linear or branched monovalent hydrocarbon chain, saturated or unsaturated, 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-;
[0114] - AK3 represents a saturated linear or branched divalent hydrocarbon chain or unsaturated in C1-C12, preferably in C1-C6, more preferably saturated in C1-C6, even more preferably in C1-C4;
[0115] - R represents a hydrogen atom, a saturated linear or branched alkyl radical or unsaturated in C1-C6, preferably in C1-C4, in particular methyl, or a radical -C(O)-C(Ra)(Rb)-C(O)-R4;
[0116] - X represents -O-, -S-, -OC(O)- or -C(O)-O-;
[0117] - Y represents -OC(O)- or -C(O)-O-;
[0118] - R4 represents a monovalent C1 to C6 hydrocarbon radical, linear or branched, saturated or unsaturated, preferably a (Ci-C4)alkyl group, in particular methyl or tert-butyl, more preferably methyl;
[0119] - Ra and Rb, identical or different, represent a hydrogen atom or a group (CrC4)alkyl, preferably a hydrogen atom;
[0120] - p denotes an integer equal to 0 or 1;
[0121] - 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;
[0122] - n denotes an integer equal to 0, 1, 2, 3 or 4; it being understood that when n is greater than 1, then the radicals -(O)t-(AKi)q-(OC(O)-C(Ra)(Rb)-C(O)-R4)u are identical or different;
[0123] -1 denotes an integer equal to 0 or 1;
[0124] - q denotes an integer equal to 0 or 1;
[0125] - u denotes an integer equal to 1, 2 or 3;
[0126] - v denotes an integer equal to 1, 2 or 3;
[0127] 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.
[0128] The compound(s) of formula (I), as well as their optical, geometric and / or solvated isomers, such as hydrates, have(s) in particular a molar mass ranging from 500 to 10,000 g / mol, more preferably a molar mass ranging from 1000 to 4000 g / mol.
[0129] Preferably, the compound(s) of formula (I), as well as their optical, geometric and / or solvated isomers, such as hydrates, is or are 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 one another 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.
[0130] 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).
[0131] 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-.
[0132] According to a first embodiment variant, the compound(s) of formula (I), as well as their optical, geometric and / or solvated isomers, such as hydrates, are such that:
[0133] - Z represents the trivalent radical -CH2-CH- CH2-;
[0134] -pestequaltoO;
[0135] -nestequaltoO;
[0136] -mestequalto3;
[0137] - AK2 represents a linear or branched monovalent hydrocarbon chain, saturated or unsaturated, 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 their combinations, in particular -O(CO)- or -C(O)-O-;
[0138] - Y, AK3, v, R, X, R4, Ra and Rb being as previously defined for the formula (i);
[0139] it being understood that the compounds contain at least 2 radicals -C(O)-C(Ra)(Rb)-C(O)-R4
[0140] According to a preferred embodiment, AK2 represents a linear or branched, saturated or unsaturated monovalent hydrocarbon chain, C12-C24, optionally substituted by one or more identical or different radicals chosen from -OR, -X-AK3-(OC(O)-C(Ra)(Rb)-C(O)-R4)v, and / or said chain being optionally interrupted by one or more heteroatoms or groups chosen from -O-, -S-, -C(O)-, and combinations thereof, in particular -OC(O)- or -C(O)-O-.
[0141] According to this embodiment variant, the compound(s) of formula (I) are in particular chosen from compounds (1), (2), (3), (4), (7), (8), (9) and (11) below, as well as their optical, geometric and / or solvated isomers, such as hydrates:
[0142] [Chem.3] (1)
[0143] [Chem.4] (2)
[0144] [Chem.5]
[0147] [Chem.8] (8) (H)
[0150] According to a second embodiment variant, the compound(s) of formula (I), as well as their optical, geometric and / or solvated isomers, such as hydrates, are such that:
[0151] -pestequaltoO;
[0152] - Z represents a multivalent hydrocarbon radical in C4 to C24, particularly in C 6 to C2oplus particularly in CM to C20, in particular Cp, linear or branched, saturated
[0153]
[0154]
[0155]
[0156]
[0157]
[0158]
[0159] 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); it being understood that said compound contains at least 2 radicals -C(O)-C(Ra)(Rb)-C(O)-R4. According to this embodiment variant, the compound(s) of formula (I) are in particular chosen from compounds (5) and (6) below, as well as their optical, geometric and / or solvated isomers, such as hydrates: [Chem. 11] K
[0160] [Chem. 12] (6)
[0161] According to a third embodiment variant, the compound(s) of formula (I), as well as their optical, geometric and / or solvated isomers, such as hydrates, are such that:
[0162] -pestequaltoO;
[0163] - n + m is equal to 4, m being non-zero;
[0164] - Z represents a tetravalent, hydrocarbon radical in C2 to C24, particularly in C3 to Cio, in particular C3, unsubstituted and uninterrupted, linear or branched, saturated or unsaturated, preferably saturated and acyclic;
[0165] - AK2 independently represent a linear monovalent hydrocarbon chain or branched, saturated or unsaturated, preferably saturated, 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;
[0166] - AK3 represents a saturated divalent linear or branched hydrocarbon chain or unsaturated in CrCi2, preferably in Ci-C6, more preferably saturated in Ci-C6, even more preferably in C2-C4, better in C3;
[0167] - v is as defined previously for formula (I); preferably v is equal to 2;
[0168] - X is as defined previously for formula (I); preferably X denotes a sulfur atom;
[0169] - Y, AK1, u, t, q, R, R4, Ra and Rb are as previously defined for the formula (i);
[0170] it being understood that said compound contains at least 2 radicals -C(O)-C(Ra)(Rb )-C(0)-R4.
[0171] According to a preferred embodiment, m is equal to 3, n is equal to 1 and u is equal to 1.
[0172] According to a preferred embodiment, t is equal to 0.
[0173] According to a preferred embodiment, q is equal to 0.
[0174] According to a preferred embodiment, Y denotes -C(O)-O.
[0175] According to a preferred embodiment, none of the AK2 radicals are interrupted.
[0176] According to a preferred embodiment, the AK2 radicals are saturated.
[0177] According to a preferred embodiment, the AK2 radicals are not substituted by - GOLD.
[0178] 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.
[0179] According to this embodiment variant, the compound(s) of formula (I) are in particular chosen from the compounds (10) below, as well as their optical, geometric and / or solvated isomers, such as the hydrates:
[0180] [Chem. 13] (10)
[0181] According to a fourth embodiment variant, the compound(s) of formula (I), as well as their optical, geometric and / or solvated isomers, such as hydrates, are such that:
[0182] - p is equal to 1;
[0183] - Z represents a multivalent hydrocarbon radical in C14 to C24, particularly in C16 to C20, preferably Cp, linear or branched, saturated or unsaturated, preferably saturated and acyclic; Z being further optionally substituted by one or more radicals -[(O)t-(AKl)q-(OC(O)-C(Ra)(Rb)-C(O)-R4)u]n, preferably being unsubstituted;
[0184] - AK2 represents a linear or branched monovalent hydrocarbon chain, saturated or unsaturated, preferably saturated, C14-C30, preferably C20-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 -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-, preferably being interrupted by -OC(O)- or -C(O)-O-;
[0185] - X is as defined previously for formula (I), preferably X denotes a sulfur atom;
[0186] - Y, AK1, AK3, n, m, v, t, q, u, R, R4, Ra and Rb being as defined previously for formula (I);
[0187] it being understood that said compound contains at least 2 radicals C(O)-C(Ra)(Rb)-C(O)-R4.
[0188] According to a preferred embodiment, n is equal to 0 and m is equal to 1.
[0189] According to a preferred embodiment, Z is a divalent radical.
[0190] 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.
[0191] According to this embodiment variant, the compound(s) of formula (I), as well as their optical, geometric and / or solvated isomers, such as hydrates, are in particular of formula (I1e):
[0192] HZY-AK4-Y'-ZH (lie)
[0193] formula (lie) in which:
[0194] - Y is as defined previously for formula (I);
[0195] - Z represents a divalent hydrocarbon radical in CM to C24, in particular in C16 to C 20, preferably Cp, linear or branched, saturated or unsaturated, preferably saturated;
[0196] - 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)-;
[0197] - 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);
[0198] 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.
[0199] According to this embodiment variant, the compound(s) of formula (I) are in particular chosen from the compounds (12) below, as well as their optical, geometric and / or solvated isomers, such as the hydrates:
[0200] [Chem. 14]
[0201] According to a fifth embodiment variant, the compound(s) of formula (I), as well as their optical, geometric and / or solvated isomers, such as hydrates, are such that:
[0202] - p is equal to 0;
[0203] - Z represents a tetravalent hydrocarbon radical in C2 to C24, in particular in C3 to Cio, preferably C4 or C5, linear or branched, saturated or unsaturated, preferably saturated and acyclic, Z being further substituted by one or more radicals -[(O)t -(AKl)q-(OC(O)-C(Ra)(Rb)-C(O)-R4)u]n, preferably n being equal to 1;
[0204] - n + m is equal to 4, preferably m is equal to 3;
[0205] - 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 C1p, 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;
[0206] - X is as defined previously for formula (I), and preferably X denotes a sulfur atom;
[0207] - Y, AK1, AK3, u, t, q, v, n, m R, R4, Ra and Rb being as defined previously for formula (I);
[0208] it being understood that said compound contains at least 2 radicals C(O)-C(Ra)(Rb )-(2(0)^,
[0209] According to a preferred embodiment, t is equal to 0 and u is equal to 1.
[0210] According to a preferred embodiment, all the AK2 radicals are identical, and preferably, all Y radicals are identical.
[0211] According to a preferred embodiment, Y denotes -OC(O)-.
[0212] According to a particular embodiment, the compounds according to this variant are of general formula (lid), as well as their optical, geometric and / or solvated isomers, such as the hydrates:
[0213] [AK'2-OCO-CH2]3-C-CH2-OC(O)-C(Ra)(Rb)-C(O)-R4 (lid)
[0214] 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(O)-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 C(O)-C(Ra)(Rb)-C(O)-R4 radicals.
[0215] According to a sixth embodiment variant, the compound(s) of formula (I), as well as their optical, geometric and / or solvated isomers, such as hydrates, are such that:
[0216] -pestequaltoO;
[0217] -m is non-zero;
[0218] - Z represents a divalent hydrocarbon radical in C2 to C24, in particular in C3 to C12, linear or branched, saturated or unsaturated, conjugated or not, preferably not conjugated, acyclic or cyclic, aromatic or not, preferably not aromatic, said radical Z being further interrupted by one or more heteroatoms or groups chosen from -O-, -N(Ra)-, -S-, -C(O)-, heterocycloalkyl(s) comprising 5 or 6 links, and combinations thereof;
[0219] - AK2 represents a linear or branched monovalent hydrocarbon chain, saturated or unsaturated, preferably saturated, 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 j-QOj-RJv, preferably unsubstituted; and / or said chain being optionally interrupted by one or more heteroatoms or groups chosen from -O-, -S-, -C(O)-, (hetero)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;
[0220] - X is as defined previously for formula (I), and preferably X denotes a sulfur atom;
[0221] - Y, AK1, AK3, v, t, q, u, R, R4, Ra and Rb being as defined previously for the formula (I),
[0222] it being understood that said compound contains at least 2 radicals C(O)-C(Ra)(Rb)-C(O)-R4.
[0223] 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 links, in particular a divalent tetrahydrofuran radical or a divalent tetrahydropyran radical, said heterocycle being optionally substituted by one or more radicals chosen from -OR, with R as defined previously for formula (I), and in particular -OH or -OC(O)-C(Ra)(Rb )-C(O)-R4).
[0224] According to a particular embodiment, the compounds according to this variant are of general formula (lie), as well as their optical, geometric and / or solvated isomers, such as the hydrates:
[0225] AK' '2-C(O)-O-(CH2)g-(heterocycle)-O-(CH2)h-(heterocycle)-(CH2)jO-CO-AK' '2 (lie)
[0226] formula (lie) in which:
[0227] - h is equal to 0, 1 or 2, preferably is equal to 0 or 1;
[0228] - g and j independently denote an integer between 1 and 3, of preference 1;
[0229] - (heterocycle) denotes a divalent heterocycloalkyl radical comprising 5 or 6 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);
[0230] - AK' '2 represents a linear or branched monovalent hydrocarbon chain, saturated or unsaturated, preferably saturated, 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;
[0231] it being understood that said compound contains at least 2 radicals -C(O)-C(Ra)(Rb)-C(O)-R4.
[0232] According to this embodiment variant, the compounds of formula (I) or (Ie) are in particular chosen from the compounds (14) below, as well as their optical isomers, geometric and / or solvated, such as hydrates:
[0233] [Chem. 15] I (14)
[0234] 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.
[0235] Preferably, the compound(s) of formula (I) is or are chosen from the following compounds of formula (Ia), as well as their optical, geometric and / or solvated isomers, such as hydrates:
[0236] Z-(Y-AK2)3 (la) formula (the) in which: - Z represents -CH2-CH-CH2- ; - AK2 independently denote a linear or branched, saturated or unsaturated monovalent hydrocarbon chain, C12-C24, optionally substituted by one or more identical or different radicals chosen from -OR and -X-AK3-(OC(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 combinations thereof, in particular -OC(O)- and -C(O)-O-; - Y, AK3, v, R, X, R4, Ra and Rb being as defined previously, preferably Y denotes -OC(O); it being understood that said compound contains at least 2 C(O)-C(Ra)(Rb)-C(O)-R4 radicals.
[0237] Preferably, the compound(s) of formula (I) is or are chosen from the following compounds of formula (Ib), as well as their optical, geometric and / or solvated isomers, such as hydrates:
[0238] m(AK2 -Y) - Z - [(O)t-(AKl)q-(OC(O)-C(Ra)(Rb)-C(O)-R4)u]n (Ib) formula (Ib) in which:
[0239] - n + m is equal to 4, m being non-zero; m and n being as defined previously;
[0240] - Z represents a tetravalent hydrocarbon radical in C2 to C24, in particular in C3 to Cio, preferably C3, unsubstituted and uninterrupted, linear or branched, saturated or unsaturated, preferably saturated and acyclic;
[0241] - AK2 independently represent a linear monovalent hydrocarbon chain or branched, saturated or unsaturated, preferably saturated, 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;
[0242] - AK3 represents a saturated linear or branched divalent hydrocarbon chain or unsaturated in CrCi2, preferably in Ci-C6, more preferably saturated in Ci-C6, even more preferably in C2-C4, preferably in C3;
[0243] - v is as defined previously, preferably v is equal to 2;
[0244] - X is as defined previously, preferably X denotes a sulfur atom;
[0245] - Y, AK1, t, q, R, R4, Ra and Rb being as defined previously;
[0246] it being understood that said compound contains at least 2 radicals -C(O)-C(Ra)(Rb )-C(O)-R4.
[0247] Preferably, the compound(s) of formula (I) is or are chosen from the following compounds of formula (Ic), as well as their optical, geometric and / or solvated isomers, such as hydrates:
[0248] m(AK2 -Y) - ZH - [(O)t-(AKl)q-(OC(O)-C(Ra)(Rb)-C(O)-R4)u]n (le)
[0249] formula (the) in which:
[0250] - Z represents a multivalent hydrocarbon radical from CM to C24, particularly in 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-(O-C(O)-C(Ra)(Rb)-C(O)-R4)u]n, preferably unsubstituted;
[0251] - AK2 represents a linear or branched monovalent hydrocarbon chain, saturated or unsaturated, preferably saturated, 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-;
[0252] - X is as defined above, and preferably X denotes a sulfur atom;
[0253] - Y, AK1, AK3, n, m, v, t, q, u, R, R4, Ra and Rb being as defined above;
[0254] it being understood that said compound contains at least 2 radicals -C(O)-C(Ra)(Rb )-C(0)-R4.
[0255] Preferably, the compound(s) of formula (I) is or are chosen from the following compounds of formula (Id), as well as their optical, geometric and / or solvated isomers, such as hydrates:
[0256] m(AK2 -Y) - Z - [(O)t-(AKl)q-(OC(O)-C(Ra)(Rb)-C(O)-R4)u]n (Id)
[0257] formula (Id) in which:
[0258] - n + m is equal to 4, preferably m is equal to 3;
[0259] - Z represents a tetravalent hydrocarbon radical in C2 to C24, in particular in C3 to Cio, in particular 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;
[0260] - AK2 independently represents a linear monovalent hydrocarbon chain or branched, saturated or unsaturated, preferably saturated, 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)-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 being uninterrupted; X is as defined above, preferably X denotes a sulfur atom; Y, AK1, AK3, v, R, Ri, Ra and Rb being as defined above,
[0261] it being understood that these compounds contain at least 2 radicals -C(O)-C(Ra)(Rb j-QOj-R,.
[0262] Preferably, the compound(s) of formula (I) is or are chosen from the following compounds of formula (Ic), as well as their optical, geometric and / or solvated isomers, such as hydrates:
[0263] m(AK2-Y) - Z - [(O)t-(AKl)q-(OC(O)-C(Ra)(Rb)-C(O)-R4)u]n (le)
[0264] formula (the) in which:
[0265] - n + m is equal to 2, m being non-zero, preferably m being equal to 2; n is such that defined previously, preferably n is zero;
[0266] - Z represents a divalent hydrocarbon radical in C2 to C24, in particular in C3 to C[2, linear or branched, saturated or unsaturated, conjugated or not, preferably not conjugated, acyclic or cyclic, aromatic or not, preferably not aromatic, said radical Z being further interrupted by one or more heteroatoms or groups chosen from -O-, -N(Ra)-, -S-, -C(O)-, (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 radical 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 above, and in particular -OH or -OC(O)-C(Ra)(Rb)-C(O)-R4);
[0267] - AK2 represents a linear or branched monovalent hydrocarbon chain, saturated or unsaturated, preferably saturated, in C14-C30, preferably C14-C24, preferably in Cp, said chain being optionally substituted by one or more identical or different radicals chosen from -OR and -X-AK3-(OC(O)-C(Ra)(Rb)-C(O)-R4)v, preferably unsubstituted; and / or said chain being optionally interrupted by one or more heteroatoms or groups chosen from -O-, -S-, -C(O)-, (hetero)cycle(s), and 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;
[0268] - X is as defined previously, preferably X denotes a sulfur atom;
[0269] - Y, AK1, AK3, v, t, q, u, R, R4, Ra and Rb being as defined previously;
[0270] it being understood that said compound contains at least 2 C(O)-C(Ra)(Rb) radicals )-C(O)-R4.
[0271] According to a preferred embodiment, the compound(s) of formula (I) are chosen from compounds (1) to (14) below, as well as their optical, geometric and / or solvated isomers, such as hydrates:
[0272] [Chem. 16] (3)
[0275] [Chem. 19]
[0277] (5) [Chem.21]
[0278] (7)
[0279] [Chem.23] (8)
[0280] [Chem.24] (10)
[0282] [Chem.26]
[0283] (H) [Chem.27]
[0284] (12) [Chem.28]
[0285] (13) [Chem.29]
[0286]
[0287] (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. According to a preferred embodiment, the compound(s) of formula (I) are chosen
[0288] among compounds (1), (3), (4), (8), (9), (10) and (11) below, as well as their optical, geometric and / or solvated isomers, such as hydrates: [Chem. 30]
[0289] (1) [Chem.31] (3) (9) (H)
[0295] Preferably, the compound(s) of formula (I) is or are chosen from the compounds of formula (I) as defined in the first variant described above, namely the compounds of formula (I) such as:
[0296] - Z represents the trivalent radical -CH2-CH- CH2-;
[0297] - p is equal to 0;
[0298] - n is equal to 0;
[0299] - m is equal to 3;
[0300] - AK2 represents a linear or branched monovalent hydrocarbon chain, saturated or unsaturated, 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 their combinations, in particular -O(CO)- or -C(O)-O-; preferably AK2 represents a linear or branched, saturated or unsaturated monovalent hydrocarbon chain, C12-C24, optionally substituted by one or more identical or different radicals chosen from -OR, -X-AK3-(OC(O)-C(Ra)(Rb)-C(O)-R4)v, and / or said chain being optionally interrupted by one or more heteroatoms or groups chosen from -O-, -S-, -C(O)-, and combinations thereof, in particular -OC(O)- or -C(O)-O-.
[0301] - Y, AK3, v, R, X, R4, Ra and Rb being as previously defined for the formula (i);
[0302] it being understood that the compounds contain at least 2 radicals -C(O)-C(Ra)(Rb)-C(O)-R4.
[0303] as well as their optical, geometric and / or solvated isomers, such as hydrates.
[0304] Preferably, the compound(s) of formula (I) is or are chosen from compounds (1), (3), (4), (7), (8), (9) and (11) as described above, as well as their optical, geometric and / or solvated isomers, such as hydrates, more preferably chosen from compounds (4) and (11) as described above, as well as their optical, geometric and / or solvated isomers, such as hydrates.
[0305] The compound(s) of formula (I) is or are present in the fatty phase in an amount ranging from 0.5% to 99.99%, better still in a content ranging from 50 to 85% by weight, relative to the total weight of the fatty phase.
[0306] The compound(s) of formula (I), as defined above, may be present in the composition according to the invention in a content ranging from 0.1 to 25% by weight, preferably in a content ranging from 0.5 to 15% by weight, even more preferably from 1 to 10% by weight relative to the total weight of the composition. Preparation of the compounds of formula (I)
[0307] The compound(s) of formula (I) may be prepared by the succession of following reactions: First step
[0308] 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 the conditions known to those skilled in the art to form an ester bond Y according to the scheme below:
[0309] (H)pZ(OH)m +mR'C0-AK'2 -> (H)pZ(OH)m,m(YAK'2)m
[0310] diagram in which:
[0311] - Y represents -OC(O)- ;
[0312] - R' denoting in particular -OH or -Cl; preferably R' denotes -OH;
[0313] - AK'2 represents a linear or branched, unsaturated hydrocarbon chain, in CrC 40, 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 their combinations, in particular -OC(O)-, -C(O)-O- or -(hetero)cycle-O-(hetero)cycle-, preferably interrupted by -O- or -S-, more preferably being uninterrupted.
[0314] According to a preferred embodiment, m is equal to m'.
[0315] The polyols (H)pZ(OH)m can be cyclic or acyclic.
[0316] As examples of cyclic (H)pZ(OH)m polyols, maltose, lactose, raffinose, sucrose, trehalose, melibiulose, melibiose, mannobiose, kojibiose, nigerose, isomaltose, rutinose, rutinulose, xylobiose or sorbitan may be cited.
[0317] As examples of acyclic (H)pZ(OH)m polyols, ethylene glycol, propylene glycol, butylene glycol, pentylene glycol, hexylene glycol, butanediol, glycerol, pentaerythritol, dipentaerythritol, trimethylolethan, mannitol, or trimethylolpropane may be cited.
[0318] 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.
[0319] 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.
[0320] The monounsaturated fatty acids are in particular chosen from palmitoleic acid, oleic acid, 9-eicosenoic acid, 11-eicosenoic acid, erucic acid and nervonic acid.
[0321] The polyunsaturated fatty acids are in particular chosen from linoleic acid, α-linolenic acid, γ-linolenic acid, dihomo-γ-linolenic acid, ara acid chidonic acid, eicosapentaenoic acid, docosahexaenoic acid, ruminic acid, monounsaturated hydroxy fatty acids chosen in particular 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 chosen in particular from densipolic acid, auricolic acid, dimorphecolic acid.
[0322] More preferably, the unsaturated fatty acid is chosen from ricinoleic acid, oleic acid, palmitoleic acid, erucic acid and mixtures thereof. Second step
[0323] 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 al 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.
[0324] 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.
[0325] 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
[0326] 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 bl illustrated in the diagram below.
[0327] 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.
[0328] 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
[0329] 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.
[0330] 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.
[0331] Compounds of structure (la), (le), such as compounds of structure (lie), compounds of structure (Id) and (le) can be obtained according to this method.
[0332] As an example, step 4 can be implemented according to the protocol described in Trevino, AS, & Trumbo, DL (2002). Acetoacetylated castor oil in coatings applications. Progress in Organic Coatings, 44(1), 49-54:
[0334]
[0335] In some cases, the compounds (H)pZ(OH)m' m (YAK'2)missus 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 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. 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: Compound
[0338]
[0339] 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, such as the products offered by Arkema under the references Vikoflex 7170 or Vikoflex 7190, can also be used as a raw material. 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: Compound al Compound hl
[0341] [Chem.56] Compound bi Compound c J
[0342] As an example, the reaction scheme below can also be implemented in which all the epoxides are opened by an alcohol, methanol in the example, then each hydroxy is esterified by t-Bu-OCOCH2CH3:
[0343] [Chem.57] Compound a2 Compound b2 b) Compound b2 Compound c2
[0345] The compounds of formula (la) to (le) can also be prepared by the following succession of reactions:
[0346] - 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:
[0347] (H)pZ(COOH)m +mHO-AK'2 -> (H)pZ(COOH)m _m(YAK'2)m
[0348] in which Y denotes -C(O)-O-, and AK'2 representing a linear or branched, unsaturated monovalent hydrocarbon chain, in C1-C40, preferably in C14-C2o, said chain being optionally interrupted by one or more heteroatoms or groups chosen from -O-, -S-, -C(O)-, (hetero)cycle(s), and their combinations, in particular -OC(O)-, -C(O)-O-, -(hetero)cycle-O-(hetero)cycle-, preferably interrupted by -O- or -S-, and more preferably not interrupted.
[0349] According to a preferred embodiment, m is equal to m'.
[0350] The polyacids (H)pZ(OH)m can be cyclic or acyclic.
[0351] The polyacids may preferably designate optionally hydroxylated dicarboxylic acids, optionally hydroxylated tricarboxylic acids, optionally hydroxylated tetracarboxylic acids.
[0352] 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 propanedioic acid, butanedioic acid and pentanedioic acid.
[0353] 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.
[0354] 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.
[0355] 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.
[0356] 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.
[0357] HO-AK'2 fatty alcohols can be mono or polyunsaturated (presence of one or more ethylenic double bonds).
[0358] HO-AK'2 fatty alcohols can contain several alcohol functions.
[0359] 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 notably chosen from 9-Octadecene-1,12-diol.
[0360] 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).
[0361] According to a preferred embodiment, the fatty alcohol HO-AK'2 is chosen from oleyl, linoleic alcohol (Linoleyl alcohol) or their mixtures.
[0362] The following steps are identical to those described previously:
[0363] - 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.
[0364] - 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.
[0365] - 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).
[0366] 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.
[0367] 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:
[0368] [Chem.59] Compound b4 Compound A4 Compound b4 Compound e4
[0369] 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):
[0370] [Chem.60] Compound b5 Compound c5
[0371] As an example, the reaction scheme below can be implemented in in which all epoxides are opened by lactic acid and then each hydroxy is esterified by t-Bu-OCOCH2CH3:
[0372] [Chem.61] Compound s6 Compound b6 Compound b6 Compound cb Fatty acid
[0373] The composition according to the invention comprises ii) one or more fatty acids.
[0374] By "fatty acid" is meant a compound comprising at least one saturated or unsaturated, linear or branched hydrocarbon chain comprising from 6 to 40 carbon atoms, the chain being substituted by one or more carboxyl groups and optionally substituted by one or more hydroxyl groups. These fatty acids are neither oxyalkylenated nor glycerolated.
[0375] Preferably, the fatty acid(s) according to the invention is or are chosen from compounds of structure R20-C(O)OH in which R20 represents a linear or branched, saturated or unsaturated hydrocarbon group, comprising from 5 to 30 carbon atoms, preferably from 7 to 29 carbon atoms, preferentially from 9 to 24 carbon atoms, better still from 11 to 19 carbon atoms, said group R20 being optionally substituted by one or more hydroxy radicals.
[0376] When R20 is an unsaturated hydrocarbon group, the unsaturation(s) are preferably ethylenic unsaturations; when several unsaturations are present, these may or may not be conjugated.
[0377] The fatty acids which can be used in the present invention are in particular chosen from myristic acid, cetyl acid (or palmitic acid), stearylic acid, arachidic acid, stearic acid, lauric acid, behenic acid, 12-hydroxystearic acid, oleic acid, linoleic acid, arachidonic acid, isostearic acid, isopalmitic acid and mixtures thereof.
[0378] In a particularly preferred manner, the fatty acid(s) is(are) chosen from lauric acid, myristic acid, palmitic acid (also called cetyl acid), stearic acid, oleic acid, linoleic acid, arachidonic acid, isostearic acid, isopalmitic acid, and mixtures thereof.
[0379] According to a preferred embodiment, the composition according to the invention comprises at least one fatty acid of structure R20-C(O)OH in which R20 represents a linear or branched, unsaturated hydrocarbon group comprising from 11 to 19 carbon atoms, said group R20 being optionally substituted by one or more hydroxy radicals, preferably unsubstituted.
[0380] According to one embodiment, the composition according to the invention comprises at least oleic acid.
[0381] The fatty acid(s) ii) is or are present in the fatty phase in a content ranging from 0.01 to 95% by weight, better still in a content ranging from 15 to 50% by weight, relative to the total weight of the fatty phase.
[0382] The fatty acid(s) ii) is or are present in the composition according to the invention in a content ranging from 0.1 to 15% by weight, preferably from 0.5 to 10%, preferentially from 1 to 5% by weight relative to the total weight of the composition. Fatty substance different from the fatty acid(s) ii)
[0383] As indicated previously, the fatty phase may contain v) at least one fatty substance, preferably at least one oil different from the fatty acids ii).
[0384] The fatty phase may thus also contain one or more oils chosen from alkanes, triglyceride oils of vegetable or synthetic origin, fatty alcohols, fatty esters other than triglyceride oils, fatty ethers, and mixtures thereof.
[0385] For the purposes of the present invention, the term “oil” denotes a liquid compound at a temperature of 25°C and atmospheric pressure (1.013.105 Pa), immiscible with water.
[0386] By "immiscible" is meant that the mixture of the same quantity of water and oil, after stirring, does not lead to a stable solution comprising only one phase, under the aforementioned temperature and pressure conditions. The observation is made with the naked eye or by means of a phase contrast microscope if necessary, on 100 g of mixture obtained after Rayneri stirring sufficient to cause a vortex to appear within the mixture (for information 200 to 1000 rpm); the resulting mixture being left to stand, in a closed bottle, for 24 hours at room temperature before observation.
[0387] It is recalled that fatty alcohols, fatty esters and fatty ethers more particularly have at least one hydrocarbon group, linear or branched, saturated or unsaturated, comprising from 6 to 40, better still from 8 to 30 carbon atoms, better still from 10 to 22 carbon atoms, optionally substituted, in particular by one or more hydroxyl groups (in particular 1 to 4). If they are unsaturated, these compounds may comprise one to three carbon-carbon double bonds, conjugated or not.
[0388] The alkanes may be chosen from: * hydrocarbon oils having 8 to 16 carbon atoms, and in particular: - branched C10-C16 alkanes such as isoalkanes such as isoalkanes (also called isoparaffins) such as C13-C16 Isoparaffin, isododecane, isodecane, isohexadecane, and for example oils sold under the trade names Isopars or Permetyls, alone or in mixtures, preferably isododecane (also called 2,2,4,4,6-pentamethylheptane), for example marketed by INEOS, more preferably isododecane; - linear alkanes, for example C10-C16, alone or in mixtures, for example such as hexane, decane, undecane, tridecane, isoparaffins such as, or n-dodecane (C12) and n-tetradecane (CM) sold by Sasol respectively under the references PARAFOL 12-97 and PARAFOL 14-97, the undecane-tridecane mixture, the mixtures of n-undecane (Cn) and n-tridecane (Ci3) obtained in examples 1 and 2 of application WO 2008 / 155059 from Cognis, and their mixtures as well as the mixtures of n-undecane (Cn) and n-tridecane (Ci3) Cetiol Ultimate® from BASF; - volatile C5-Ci2 cyclic, non-aromatic alkanes; *hydrocarbon oils chosen in particular from linear or branched compounds, of mineral or synthetic origin such as for example: i) paraffin oil, ii) squalane such as the reference NEOSSANCE SQUALANE marketed by AMYRIS, isoeicosane, iii) mixtures of linear, saturated hydrocarbons, particularly in Ci4-C30, more particularly in Ci5-C28, such as mixtures whose INCI names are for example the following: C15-C19 alkane, Ci8-C2i alkane, C2rC28 alkane, such as for example the products Gemseal 40, Gemseal 60, Gemseal 120 marketed by Total, Emogreen L19 marketed by SEPPIC, Emogreen L15 marketed by SEPPIC, Emogreen HP40, marketed by SEPPIC, iv) polybutenes, hydrogenated or no, such as for example products from the Indopol range marketed by the company INEOS Oligomers, products with the INCI name HYDROGENATED POLYISOBUTENE;(v) polyisobutenes, hydrogenated or not, preferably hydrogenated, such as, for example, the non-volatile compounds of the Parléam® range marketed by the company NIPPON OIL FATS, (vi) polydecenes, hydrogenated or not, such as, for example, the non-volatile compounds of the PURESYN® range marketed by the company Exxonmobil), (vii) decene / butene copolymers, butene / isobutene copolymers and (viii) their mixtures.;
[0389] The triglyceride oils of vegetable or synthetic origin are preferably triglycerides consisting of fatty acid esters and glycerol which are liquid at room temperature, in particular the fatty acids of which may have chain lengths varying from C7 to C22. These oils may be linear or branched, saturated or unsaturated.Examples include heptanoic or octanoic triglycerides, caprylic / capric acid triglycerides, caprylic / capric / succinic acid triglycerides; vegetable oils such as wheat germ, sunflower, grape seed, sesame, cumin, corn, apricot kernel, castor, shea, avocado, olive, soybean, sweet almond, palm, rapeseed, cotton, hazelnut, macadamia, jojoba, alfalfa, poppy, pumpkin, squash, blackcurrant, evening primrose, millet, barley, quinoa, rye, safflower, candlenut, passionflower, musk rose, peanut, coconut, argan, passionflower, kaya; the liquid fraction of shea butter, and the liquid fraction of cocoa butter; as well as mixtures thereof.
[0390] The fatty alcohols are in particular saturated or unsaturated, linear or branched, and in particular comprise from 10 to 26 carbon atoms. They are preferably mono-alcohols. Advantageously, the C10-C26 alcohols are fatty alcohols, preferably branched or unsaturated when they comprise at least 14 carbon atoms. Preferably, the fatty alcohol comprises from 10 to 24 carbon atoms, and more preferably from 12 to 22 carbon atoms, such as in particular lauryl alcohol, isostearyl alcohol, oleyl alcohol, 2-butyloctanol, 2-undecyl pentadecanol, 2-hexyldecyl alcohol, isocetyl alcohol, octyldodecanol and mixtures thereof.
[0391] The fatty esters other than the triglyceride oils mentioned above, have a total number of carbon atoms greater than or equal to 8, more advantageously greater than or equal to 10. They can be chosen from: (i) linear aliphatic esters of formula RC(O)-OR' in which RC(O)-O-represents the carboxylic acid residue containing from 2 to 40 carbon atoms, and R' represents a hydrocarbon chain containing from 1 to 40 carbon atoms, aliphatic hydrocarbon esters of alkylene glycol, in particular ethylene glycol or propylene glycol; the total number of carbon atoms being advantageously at least 10.Examples of such esters include, for example, isoamyl laurate, cetostearyl octanoate, isopropyl myristate, isopropyl palmitate, isopropyl stearate or isostearate, ethyl palmitate, 2-ethylhexyl palmitate, isostearyl isostearate, octyl stearate, isostearyl heptanoate, cetyl octanoate, coco caprylate caprate, tridecyl octanoate, 2-ethylhexyl palmitate, hexyl laurate, neopentanoic acid esters such as isodecyl neopentanoate, isotridecyl neopentanoate, neopentanoate isostearyl, 2-octyldocecyl neopentanoate, isononanoic acid esters. such as isononyl isononanoate, isotridecyl isononanoate, octyl isononanoate, oleyl erucate; isocetyl stearate, isodecyl neopentanoate, isostearyl behenate, myristyl myristate; (ii) fatty acid esters of alcohols or polyols such as polyglycerol-2 triisostearate; glyceryl triisostearate; glyceryl 2-tridecyl tetradecanoate; propylene glycol dioctanoate, polyethylene glycol diheptanoate, propylene glycol 2-diethylhexanoate, pentaerythrityl tetraisostearate, pentaerythrityl tetrape-largonate; pentaerythrityl 2-tetradecyl tetradecanoate; pentaerythrityl tetraisostearate; pentaerythrityl tetraisononanoate; (iii) aromatic esters such as tridecyl trimellitate, C12-C15 alcohol benzoate, 2-phenyl ethyl ester of benzoic acid, butyl octyl salicylate; iv) fatty esters of alpha hydroxy acids, polyacids or amino acids such as triisoarachidyl citrate, lauroyl isopropyl sarcosinate, dii-isopropyl sebacate; (v) polyesters obtained by condensation of dimer and / or trimer of unsaturated fatty acid and diol such as those with the INCI name dilinoleic acid / butanediol copolymer, dilinoleic acid / propanediol copolymer; polyesters obtained by condensation of dimer of fatty acid and dimer diol such as dimer dilinoleyl dimer dilinoleate; vi) carbonates of formula Ri-OC(O)-O-R2, with Ri and R2, identical or different, represent a C4 to C12, and preferably C6 to C10, alkyl chain, linear or branched; the total number of carbon atoms in the carbonate being advantageously at least 10. The carbonate oils may be dicaprylyl carbonate (or dioctyl carbonate), marketed under the name Cetiol CC® by the company BASF, di(ethyl-2-hexyl)carbonate, marketed under the name TEGOSOFT DEC® by the company Evonik, dipropylheptyl carbonate (Cetiol 4 Ail from BASF), dibutyl carbonate; di-neopentyl carbonate; dipentyl carbonate; di-neoheptyl carbonate; di-heptyl carbonate; di-isononyl carbonate; or di-nonyl carbonate; and preferably dioctyl carbonate; vii) and their mixtures.
[0392] Among the liquid fatty ethers, there are included the oils of formula R3-O-R4 in which R3 and R4 independently denote a linear, branched or cyclic C6-C24 alkyl group, preferably a C6-C18 alkyl group, and more preferably a C8-C12 alkyl group. It may be preferable for R3 and R4 to be identical. As a linear alkyl group, mention may be made of a hexyl group, a heptyl group, an octyl group, a nonyl group, a decyl group, an undodyl group, a dodecyl group, a tridecyl group, a tetradecyl group, a pentadecyl group, a hexadecyl group, a heptadecyl group, an octadecyl group, a non-nadecyl group, an eicosyl group, a behenyl group, a docosyl group, a group tricosyl and a tetracosyl group. As a branched alkyl group, there may be mentioned a 1,1-dimethylpropyl group, a 3-methylhexyl group, a 5-methylhexyl group, an ethylhexyl group, a 2-ethylhexyl group, a 5-methyloctyl group, a 1-ethylhexyl group, a 1-butylpentyl group, a 2-butyloctyl group, an isotridecyl group, a 2-pentylnonyl group, a 2-hexyldecyl group, an isostearyl group, a 2-heptylundecyl group, a 2-octyldodecyl group, a 1,3-dimethylbutyl group, a 1-(1-methylethyl)-2-methylpropyl group, a 1,1,3,3-tetramethylbutyl group, a 3,5,5-trimethylhexyl group, a 1-(2-methylpropyl)-3-methylbutyl group, a 3,7-dimethyloctyl group, and a 2-(1,3,3-trimethylbutyl)-5,7,7-trimethyloctyl group. As a cyclic alkyl group, there may be mentioned a cyclohexyl group, a 3-methylcyclohexyl group and a 3,3,5-trimethylcyclohexyl group.
[0393] Examples of liquid fatty ethers that may be mentioned include caprylyl ether, dilau-rylether, diisostearyl ether, dioctyl ether, nonylphenyl ether, dodecyl dimethyl-butyl ether, cetyl dimethylbutyl ether, cetyl isobutyl ether and mixtures thereof, better still caprylyl ether, such as the reference CETIOL OE marketed by BASF.
[0394] The fatty body(ies) of the fatty phase are preferentially chosen from triglyceride oils of vegetable or synthetic origin, fatty alcohols, fatty esters other than triglyceride oils, and mixtures thereof.
[0395] A3. Coloring agent
[0396] As indicated above, the composition according to the invention optionally comprises iv) at least one coloring agent.
[0397] The composition according to the invention preferably comprises iv) at least one coloring agent.
[0398] The coloring agent(s) iv) is or are chosen from pigments. Pigment
[0399] By "pigment" is meant all pigments providing color to keratin materials. Their solubility in water at 25°C and at atmospheric pressure (760 mmHg) is less than 0.05% by weight, and preferably less than 0.01% by weight.
[0400] The pigments which can be used are in particular chosen from organic and / or mineral pigments known in the art, in particular those which are described in the Kirk-Othmer encyclopedia of chemical technology and in the Ullmann encyclopedia of industrial chemistry.
[0401] They can be natural, of natural origin, or not.
[0402] These pigments can be in the form of powder or pigment paste. They can be coated or uncoated.
[0403] The pigments can for example be chosen from mineral pigments, organic pigments, lakes, special effect pigments such as mother-of-pearl or glitter, and their mixtures.
[0404] The pigment may be a mineral pigment. By mineral pigment is meant any pigment which meets the definition of the Ullmann encyclopedia in the inorganic pigment chapter. Among the mineral pigments useful in the present invention, mention may be made of iron or chromium oxides, manganese violet, ultramarine blue, chromium hydrate, ferric blue and titanium oxide.
[0405] The pigment may be an organic pigment. By "organic pigment" is meant any pigment that meets the definition of the Ullmann encyclopedia in the organic pigment chapter.
[0406] The organic pigment may in particular be chosen from nitroso, nitro, azo, xanthene, pyrene, quinoline, quinoline, anthraquinone, triphenylmethane, fluorane, phthalocyanine, metal complex type compounds, isoindolinone, isoindoline, qui-nacridone, perinone, perylene, diketopyrrolopyrrole, indigo, thioindigo, dioxazine, triphenylmethane, quinophthalone.
[0407] In particular, the white or colored organic pigments may be chosen from carmine, carbon black, aniline black, azo yellow, quinacridone, phthalocyanine blue, the blue pigments codified in the Color Index under the references Cl 42090, 69800, 69825, 74100, 74160, the yellow pigments codified in the Color Index under the references Cl 11680, 11710, 19140, 20040, 21100, 21108, 47000, 47005, the green pigments codified in the Color Index under the references Cl 61565, 61570, 74260, the orange pigments codified in the Color Index under the references Cl 11725, 45370, 71105, the red pigments codified in the Color Index under the references CI 12085, 12120, 12370, 12420, 12490, 14700, 15525, 15580, 15620, 15630, 15800, 15850, 15865, 15880, 26100, 45380, 45410, 58000, 73360, 73915, 75470, the pigments obtained by oxidative polymerization of indole, phenolic derivatives as described in patent FR 2 679 771.
[0408] As an example, we can also cite organic pigment pigment pastes such as the products sold by the company HOECHST under the name: - COSMENYL YELLOW IOG: Pigment YELLOW 3 (Cl 11710); - COSMENYL YELLOW G: Pigment YELLOW 1 (Cl 11680); - ORANGE COSMENYL GR: Pigment ORANGE 43 (Cl 71105); - COSMENYL RED R: Pigment RED 4 (Cl 12085); - CARMIN COSMENYL FB: Pigment RED 5 (Cl 12490); - VIOLET COSMENYL RL: Pigment VIOLET 23 (Cl 51319); - COSMENYL BLUE A2R: Pigment BLUE 15.1 (Cl 74160); - VERT COSMENYL GG: Pigment GREEN 7 (Cl 74260); - COSMENYL BLACK R: Pigment BLACK 7 (Cl 77266).
[0409] The pigments in accordance with the invention may also be in the form of pigments composites as described in patent EP 1 184 426. These composite pigments may be composed in particular of particles comprising an inorganic core, at least one binder ensuring the fixing of the organic pigments on the core, and at least one organic pigment at least partially covering the core.
[0410] The organic pigment may also be a lake. By lake is meant dyes adsorbed on insoluble particles, the whole thus obtained remaining insoluble during use.
[0411] The inorganic substrates on which the dyes are adsorbed are, for example, alumina, silica, calcium and sodium borosilicate or calcium and aluminum borosilicate, and aluminum.
[0412] Among the colorants, we can cite carminic acid. Also included are dyes known under the following names: D & C Red 21 (CI 45 380), D & C Orange 5 (CI 45 370), D & C Red 27 (CI 45 410), D & C Orange 10 (CI 45 425), D & C Red 3 (CI 45 430), D & C Red 4 (CI 15 510), D & C Red 33 (CI 17 200), D & C Yellow 5 (CI 19 140), D & C Yellow 6 (CI 15 985), D & C Green (CI 61 570), D & C Yellow 1 O (CI 77 002), D & C Green 3 (CI 42 053), D & C Blue 1 (CI 42 090).
[0413] Examples of lacquers include the product known under the following name: D & C Red 7 (CI 15 850:1).
[0414] The pigment may also be a special effect pigment. Special effect pigments are understood to mean pigments that generally create a colored appearance (characterized by a certain shade, a certain vividness and a certain clarity) that is non-uniform and changes depending on the viewing conditions (light, temperature, viewing angles, etc.). They are thus opposed to colored pigments that provide a conventional uniform opaque, semi-transparent or transparent shade.
[0415] There are several types of special effect pigments, those with a low refractive index such as fluorescent or photochromic pigments, and those with a higher refractive index such as nacres, interference pigments or glitter.
[0416] Examples of special effect pigments include pearlescent pigments such as mica coated with titanium or bismuth oxychloride, colored pearlescent pigments such as mica coated with titanium and iron oxides, mica coated with iron oxide, mica coated with titanium and in particular ferric blue or chromium oxide, mica coated with titanium and an organic pigment as defined above, and pearlescent pigments based on bismuth oxychloride. Pearlescent pigments include Cellini pearlescent pigments marketed by BASF (Mica-TiO 2-lake), Prestige pearlescent pigments marketed by Eckart (Mica-TiO2), Prestige Bronze pearlescent pigments marketed by Eckart (Mica-Fe2O3) and Colorona pearlescent pigments marketed by Merck (Mica-TiO2-Fe2 O3).
[0417] Mention may also be made of gold-colored mother-of-pearls marketed in particular by BASF under the name Brillant gold 212G (Timica), Gold 222C (Cloisonne), Sparkle Gold (Timica), Gold 4504 (Chromalite) and Monarch gold 233X (Cloisonne); bronze mother-of-pearls marketed in particular by MERCK under the name Bronze fine (17384) (Colorona) and Bronze (17353) (Colorona) and by BASF under the name Super bronze (Cloisonne); orange mother-of-pearls marketed in particular by BASF under the name Orange 363C (Cloisonne) and Orange MCR 101 (Cosmica) and by MERCK under the name Passion orange (Colorona) and Matte orange (17449) (Microna); brown-tinted mother-of-pearl, notably marketed by BASF under the name Nu-antique Copper 340XB (Cloisonne) and Brown CL4509 (Chromalite); copper-reflecting mother-of-pearl, notably marketed by BASF under the name Copper 340A (Timica);red-tinted mother-of-pearl, notably marketed by MERCK under the name Sienna Fine (17386) (Colorona); yellow-tinted mother-of-pearl, notably marketed by BASF under the name Yellow (4502) (Chromalite); red-tinted mother-of-pearl with a gold tint, notably marketed by BASF under the name Sunstone G012 (Gemtone); pink mother-of-pearl, notably marketed by BASF under the name Tan opale G005 (Gemtone);black mother-of-pearl with a gold sheen, notably marketed by BASF under the name Nu antique bronze 240 AB (Timica), blue mother-of-pearl notably marketed by MERCK under the name Matte Blue (17433) (Microna), white mother-of-pearl with a silver sheen, notably marketed by MERCK under the name Xirona Silver and pinkish-orange, golden-green mother-of-pearl notably marketed by MERCK under the name Indian Summer (Xirona) and their mixtures.;
[0418] Still as an example of nacres, we can also cite particles comprising a borosilicate substrate coated with titanium oxide.
[0419] Particles with a glass substrate coated with titanium oxide are sold in particular under the name METASHINE MC1080RY by the company TOYAL.
[0420] Finally, as examples of nacres, mention may also be made of polyethylene terephthalate flakes, in particular those marketed by the company Meadowbrook Inventions under the name Silver IP 0.004X0.004 (silver flakes). Multilayer pigments based on synthetic substrates such as alumina, silica, calcium and sodium borosilicate or calcium and aluminum borosilicate, and aluminum may also be considered.
[0421] The special effect pigments can also be chosen from reflective particles, that is to say in particular particles whose size, structure, in particular the thickness of the layer(s) which constitute it and their physical nature and chemical, and the surface state, allow them to reflect incident light. This reflection may, where appropriate, have sufficient intensity to create on the surface of the composition or mixture, when it is applied to the support to be made up, highlights visible to the naked eye, that is to say brighter points which contrast with their environment by appearing to shine.
[0422] The reflective particles may be selected so as not to significantly alter the coloring effect generated by the coloring agents associated with them and more particularly so as to optimize this effect in terms of color rendering. They may more particularly have a yellow, pink, red, bronze, orange, brown, gold and / or copper color or reflection.
[0423] These particles can have various shapes, in particular being platelet-shaped or globular, in particular spherical.
[0424] The reflective particles, whatever their shape, may have a multi-layer structure or not and, in the case of a multi-layer structure, for example at least one layer of uniform thickness, in particular of a reflective material.
[0425] When the reflective particles do not have a multilayer structure, they may be composed, for example, of metal oxides, in particular titanium or iron oxides obtained by synthesis.
[0426] When the reflective particles have a multi-layer structure, they may for example comprise a natural or synthetic substrate, in particular a synthetic substrate at least partially coated with at least one layer of a reflective material, in particular at least one metal or metallic material. The substrate may be single-material, multi-material, organic and / or inorganic.
[0427] More particularly, it can be chosen from glasses, ceramics, graphite, metal oxides, aluminas, silicas, silicates, in particular aluminosilicates and borosilicates, synthetic mica and their mixtures, this list not being limiting.
[0428] The reflective material may comprise a layer of metal or a metallic material.
[0429] Reflective particles are described in particular in documents JP-A-09188830, JP-A-10158450, JP-A-10158541, JP-A-07258460 and JP-A-05017710.
[0430] Still as an example of reflective particles comprising a mineral substrate coated with a layer of metal, mention may also be made of particles comprising a borosilicate substrate coated with silver.
[0431] Platelet-shaped particles with a silver-coated glass substrate are sold under the name MICROGLASS METASHINE REFSX 2025 PS by TOYAL. Particles with a nickel / chromium / molybdenum alloy-coated glass substrate are sold under the name CRYSTAL STAR GF 550, GF 2525 by this same company.
[0432] It is also possible to use particles comprising a metallic substrate such as silver, aluminum, iron, chromium, nickel, molybdenum, gold, copper, zinc, tin, magnesium, steel, bronze, titanium, said substrate being coated with at least one layer of at least one metallic oxide such as titanium oxide, aluminum oxide, iron oxide, cerium oxide, chromium oxide, silicon oxides and mixtures thereof.
[0433] Examples include aluminum, bronze or copper powders coated with SiO2 marketed under the name VISIONAIRE by the company ECKART.
[0434] Mention may also be made of interference effect pigments not fixed on a substrate such as liquid crystals (Helicones HC from Wacker), interference holographic flakes (Geometry Pigments or Spectra f / x from Spectratek). Special effect pigments also include fluorescent pigments, whether they are substances that fluoresce in daylight or that produce ultraviolet fluorescence, phosphorescent pigments, photochromic pigments, thermochromic pigments and quantum dots, marketed for example by the company Quantum Dots Corporation.
[0435] The variety of pigments that can be used in the present invention makes it possible to obtain a rich palette of colors, as well as particular optical effects such as metallic and interference effects.
[0436] The size of the pigment used in the composition according to the present invention is generally between 10 nm and 200 qm, preferably between 20 nm and 80 qm, and more preferably between 30 nm and 50 qm.
[0437] The pigments may be dispersed in the composition using a dispersing agent.
[0438] The dispersing agent serves to protect the dispersed particles against agglomeration or flocculation. This dispersing agent may be a surfactant, an oligomer, a polymer or a mixture of several of them, carrying one or more functionalities having a strong affinity for the surface of the particles to be dispersed. In particular, they may attach physically or chemically to the surface of the pigments. These dispersants also have at least one functional group that is compatible or soluble in the continuous medium.In particular, esters of 12-hydroxystearic acid in particular and of C8 to C20 fatty acid and polyol such as glycerol, diglycerin, such as poly(12-hydroxystearic acid) stearate with a molecular weight of approximately 750g / mol such as that sold under the name Solsperse 21 000 by the company Avecia, polyglyceryl-2 dipolyhydroxystearate (CTFA name) sold under the reference Dehymyls PGPH by the company Henkel or polyhydroxystearic acid such as that sold under the reference Arlacel P100 by the company Uniqema and their mixtures are used.
[0439] As another dispersant that can be used in the compositions of the invention, mention may be made of quaternary ammonium derivatives of polycondensed fatty acids such as Solsperse 17 000 sold by the company Avecia, poly dimethylsiloxane / oxypropylene mixtures such as those sold by the company Dow Corning under the references DC2-5185, DC2-5225 C.
[0440] The pigments used in the composition may be surface-treated with an organic agent.
[0441] Thus, the previously surface-treated pigments useful in the context of the invention are pigments which have undergone totally or partially a surface treatment of a chemical, electronic, electrochemical, mechanochemical or mechanical nature, with an organic agent such as those which are described in particular in Cosmetics and Toiletries, February 1990, Vol. 105, p. 53-64 before being dispersed in the composition in accordance with the invention.These organic agents may be chosen, for example, from waxes, for example carnauba wax and beeswax; fatty acids, fatty alcohols and their derivatives, such as stearic acid, hydroxystearic acid, stearyl alcohol, hydroxystearyl alcohol, lauric acid and their derivatives; anionic surfactants; lecithins; sodium, potassium, magnesium, iron, titanium, zinc or aluminum salts of fatty acids, for example aluminum stearate or laurate; metal alkoxides; polyethylene; (meth)acrylic polymers, for example polymethylmethacrylates; polymers and copolymers containing acrylate units; alkanoamines; silicone compounds, for example silicones, in particular polydimethylsiloxanes; fluorinated organic compounds, for example perfluoroalkyl ethers; fluorosilicon compounds.
[0442] The surface-treated pigments useful in the composition may also have been treated with a mixture of these compounds and / or have undergone several surface treatments.
[0443] The surface-treated pigments useful in the context of the present invention can be prepared according to surface treatment techniques well known to those skilled in the art or found as such commercially.
[0444] Preferably, the surface-treated pigments are covered by an organic layer.
[0445] The organic agent with which the pigments are treated can be deposited on the pigments by solvent evaporation, chemical reaction between the molecules of the surfactant or creation of a covalent bond between the surfactant and the pigments.
[0446] The surface treatment can thus be carried out for example by chemical reaction of a surfactant with the surface of the pigments and creation of a covalent bond between the surfactant and the pigments or fillers. This method is in particular described in US patent 4,578,266.
[0447] Preferably, an organic agent covalently bound to the pigments will be used.
[0448] The surface treatment agent may represent from 0.1 to 50% by weight of the total weight of the surface-treated pigment, preferably from 0.5 to 30% by weight, and even more preferably from 1 to 20% by weight of the total weight of the surface-treated pigment.
[0449] Preferably, the surface treatments of the pigments are chosen from the following treatments:
[0450] - a PEG-Silicone treatment such as the AQ surface treatment marketed by LCW;
[0451] - a Methicone treatment such as the SI surface treatment marketed by LCW;
[0452] - a Dimethicone treatment such as Covasil 3.05 com surface treatment marketed by LCW;
[0453] - a Dimethicone / Trimethylsiloxysilicate treatment as the surface treatment Covasil 4.05 marketed by LCW;
[0454] - a Magnesium Myristate treatment such as the MM com surface treatment marketed by LCW;
[0455] - an Aluminum Dimyristate treatment such as MI com surface treatment sold by Miyoshi;
[0456] - a Perfluoropolymethylisopropyl ether treatment as the surface treatment FHC marketed by LCW;
[0457] - an Isostearyl Sebacate treatment like the commercialized HS surface treatment by Miyoshi;
[0458] - a Perfluoroalkyl Phosphate treatment such as PF surface treatment marketed by Daito;
[0459] - an acrylate / Dimethicone and Perfluoroalkyl Phosphate Copolymer treatment such as the FSA surface treatment marketed by Daito;
[0460] - a Polymethylhydrogen siloxane / Perfluoroalkyl Phosphate treatment such as the FS01 surface treatment marketed by Daito;
[0461] - an Acrylate / Dimethicone Copolymer treatment as the surface treatment ASC marketed by Daito;
[0462] - an Isopropyl Titanium Triisostearate treatment such as the ITT surface treatment marketed by Daito;
[0463] - an Acrylate copolymer treatment such as APD surface treatment com sold by Daito;
[0464] - a Perfluoroalkyl Phosphate / Isopropyl Titanium Triisostearate treatment such as the PF + ITT surface treatment marketed by Daito.
[0465] According to a particular embodiment of the invention, the dispersing agent is present with organic or inorganic pigments in particulate form of sub-micron size.
[0466] By "sub-micronic" or in English "sub-micronic" is meant pigments whose particle size has been micronized by micronization method and whose average particle size is less than one micrometer (pm), in particular between 0.1 and 0.9 pm, and preferably between 0.2 and 0.6 pm.
[0467] According to one embodiment, the dispersing agent and the pigment(s) are present in an amount (dispersant: pigment), according to a weight ratio, of between 1:4 and 4:1, particularly between 1.5:3.5 and 3.5:1 or better between 1.75:3 and 3:1.
[0468] The dispersing agent(s) may therefore have a silicone backbone, such as silicone polyether and amino-silicone dispersants. Suitable dispersing agents include:
[0469] - amino-silicones ie silicones comprising one or more amino groups such than those marketed under the names and references: BYK LPX 21879, by BYK, GP-4, GP-6, GP-344, GP-851, GP-965, GP-967 and GP-988-1, marketed by Genesee polymers,
[0470] - silicone acrylates such as Tego ® RC 902, Tego ® RC 922, Tego ® RC 1041, and Tego ® RC 1043, marketed by Evonik,
[0471] - polydimethylsiloxane silicones (PDMS) with carboxylic groups such as X- 22162 and X-22370 by Shin-Etsu, silicone epoxy such as GP-29, GP-32, GP-502, GP-504, GP-514, GP-607, GP-682, and GP-695, by Genesee Polymers, or Tego ® RC 1401, Tego ® RC 1403, Tego ® RC 1412, by Evonik.
[0472] According to a particular embodiment, the dispersing agent(s) are of amino-silicone type and are cationic.
[0473] Preferably, the pigment(s) is (are) chosen from mineral, mixed mineral-organic or organic pigments.
[0474] In one variant of the invention, the pigment(s) are organic pigments, preferably organic pigments surface-treated with an organic agent chosen from silicone compounds. In another variant of the invention, the pigment(s) are mineral pigments.
[0475] Preferably, the pigment(s) are chosen from iron oxides, in particular red, brown or black. As an example of iron oxide, mention may be made of red iron oxide.
[0476] The pigment(s) as defined above may be present in the composition according to the invention in a content ranging from 0 to 20% by weight, preferably in a content ranging from 0 to 15% by weight, better still in a content ranging from 0 to 10%, relative to the total weight of the composition.
[0477] Advantageously, the pigment(s) may be present in a total content ranging from 0.05 to 20% by weight, preferably from 0.1 to 15% by weight, better still from 0.5 to 10% by weight relative to the total weight of the composition.
[0478] A4. Addenda)
[0479] The composition according to the invention may further comprise one or more additives. The additives are different from the compound(s) ii), iii), iv) and v) as described above.
[0480] The additive(s) possibly present in the composition according to the invention may be included in the aqueous phase or the fatty phase.
[0481] The composition according to the invention may thus further comprise one or more additives chosen from the group consisting of salts; emollients; moisturizers; perfumes; peptizers; vitamins; thickeners; suspenders; conditioning agents; preservatives; anionic, cationic, non-ionic and amphoteric polymers.
[0482] A person skilled in the art will take care to choose any additives and their quantity so that they do not harm the cosmetic properties of the composition of the present invention.
[0483] These additives may be present in the composition according to the invention in an amount ranging from 0 to 20% by weight relative to the total weight of the composition.
[0484] Preferably, among the additives, mention may in particular be made of glycerin.
[0485] According to one embodiment, the aqueous phase comprises water, iii) at least chitosan, as described previously, at least one acid having a pKa of less than 5, as described previously, and at least glycerin.
[0486] The composition according to the invention may further comprise at least one (poly)amine compound different from the chitosan(s) iii). (Poly)amino compounds
[0487] The (poly)amine compound different from the chitosan(s) iii) 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.
[0488] The (poly)amino compound may be a compound comprising from 2 to 20 carbon atoms, in particular a non-polymeric compound, 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 their associations such as -Si(R')2-O- or -O-Si(R')2-, with R', identical or different, re having a (Ci-C4)alkyl group such as methyl, and R” representing a hydrogen atom or a (Ci-C4)alkyl group, preferably a hydrogen atom.
[0489] By "non-polymeric compound" is meant a compound which is not directly obtained by a polymerization reaction of monomers.
[0490] 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, 1,2-bis(3-aminopropylamino)ethane, N,N'-bis(3-aminopropyl)-1,3-propanediamine, ethylenediamine, 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-l,13-tridecanediamine.
[0491] 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).
[0492] 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:
[0493] - R' i is a linear or branched, saturated or unsaturated, cyclic or acyclic substituted by a group chosen from the primary amine groups NH2 or secondary -N(H)R with R representing a Cr-C4 alkyl, an aryl, a benzyl substituted by an amino group or by a Cr-C4 aminoalkyl group; R\ being able to be interrupted in its chain by a heteroatom (O, S, NH) or a carbonyl group C(O), R\ being linked to the silicon atom directly via a carbon atom,
[0494] - R'2 and R'3, identical or different, represent a linear (Ci-C6)alkyl group or branched,
[0495] - z denotes an integer ranging from 1 to 3, and
[0496] - x denotes an integer ranging from 0 to 2,
[0497] with z + x = 3.
[0498] In particular, R' i is an acyclic chain.
[0499] Preferably, R' i is a linear or branched C1-C6 hydrocarbon chain, saturated or unsaturated, 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 precisely preferably, R\ is a linear saturated C1-C6 hydrocarbon chain substituted by an NH2 amine group. Even more preferably, R' i is a linear saturated C2-C4 hydrocarbon chain substituted by an NH2 amine group.
[0500] 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.
[0501] In particular, R'3 represents an alkyl group comprising from 1 to 4 carbon atoms, preferably, R'3 represents a linear alkyl group comprising from 1 to 4 carbon atoms, and more preferably R'3 represents the methyl or ethyl group. Preferably, z is equal to 3.
[0502] 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.
[0503] 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.
[0504] The (poly)amino compound may also be chosen from amino polymers different from the chitosan(s) iii), 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 *.
[0505] According to a particular embodiment of the invention, the (poly)amine compound(s) are monoamine and chosen from polydialkylsiloxanes, in particular of formula (IV):
[0506] 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 (Ci-C4)alkyl group such as methyl, and - R'4 represents a linear or branched (Ci-C6)alkyl group, 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 *. Examples of polydimethylsiloxanes (IV) include those sold under the names “MCR-A11” and “MCR-A12” by the company Gelest.
[0507] 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).
[0508] More particularly, they are chosen from the compounds of formulas (V) or (VI): • ALK[(O-ALK')m-NH2]2 (V)
[0509] 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.mol *.
[0510] 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.
[0511] 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”, 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-l,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.
[0512] 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.
[0513] As (poly)amino compounds which are triaminated, triaminated polyethers are particularly cited, and in particular polyethylene glycol and / or polypropylene glycol a, co-diamine (with amine function at the end of the chain) such as those sold under the name Jeffamine T-403.
[0514] 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).
[0515] In this variant, the (poly)amine compound(s) are 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.
[0516] Preferably, the polyamine compounds are chosen from polydimethylsiloxanes comprising primary amine groups at the end of the chain and / or on side chains.
[0517] 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.;
[0518] 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):
[0519] 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 at 500000 g.mol *.
[0520] 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 *.
[0521] Examples of polydimethylsiloxanes of formula (VI) include those sold under the names “AMS-132”, “AMS-152”, “AMS-162”, “AMS-163”, “AMS-191” and “AMS-1203” by the company Gelest.
[0522] According to another variant, the formula (VII) is such that Ra represents a hydroxyl or (Ci-C4)alkyl group, such as methyl, ALK1 represents a (C5-C6)alkylene group substituted by an NH group, preferably ALK1 represents -(CH2)3 -N(H)-(CH2)2-, and m and n are such that the weight-average molecular mass of the compound of formula (VI) ranges from 5000 g.mol1 to 500000 g.mol *.
[0523] As amino polymers, polytetrahydrofuran (or polytetramethylene glycol) a, co-diamine, and polybutadienes a, co-diamine may also be cited.
[0524] 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.
[0525] According to a preferred embodiment, the composition comprises at least one (poly)amine compound different from the chitosan(s) iii), in particular chosen from aminoalkoxysilanes, polydimethylsiloxanes comprising primary amine groups at the end of the chain or on side chains, amodimethicones, polyglucosamines, spermidine, and mixtures thereof.
[0526] According to a preferred embodiment, the composition comprises at least one (poly)amine compound different from the chitosan(s) iii) chosen from:
[0527] ib) polyether diamines, in particular polyethylene glycol a, co-diamine, with an amine function at the end of the chain,
[0528] ic) polyether triamines, in particular polyetheramine (or jeffamine),
[0529] id) aminoalkoxysilanes, in particular APTES,
[0530] ie) the 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
[0531] 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 with bis(3-aminopropyl) (PDMS-diNH2) and amodimethicones comprising amine groups on side chains, more particularly bis-cetearyl amo-dimethicone; A. Method(s) of producing the composition
[0532] Preferably, the composition according to the invention comprises: a. at least one fatty phase comprising i) at least one compound of formula (I) as well as its optical, geometric and / or solvated isomers, such as hydrates, as defined previously; and ii) at least one fatty acid, as defined previously, b. at least one aqueous phase comprising iii) at least one chitosan at least one acid, preferably organic, having a pKa less than 5, and water. c. at least one pigment.
[0533] According to this preferred embodiment, the aqueous phase comprises at least one acid having a pKa of less than 5, in particular at least one carboxylic acid of formula (Q), as defined above, having a pKa of less than 5. Preferably, the acid having a pKa of less than 5 is lactic acid.
[0534] According to this preferred embodiment, the aqueous phase preferably has a pH less than or equal to 6.
[0535] Preferably, the composition according to the invention comprises: a. at least one fatty phase comprising at least one compound of formula (I) i) chosen from compounds (1), (3), (4), (7), (8), (9), and (11), in particular chosen from compounds (4) and (11) as described above, as well as their salts, isomers and solvates; and at least one fatty acid corresponding to the structure Rioo-C(O)OH with Ri00 corresponding to an alkyl group comprising from 14 to 20 carbon atoms, b. at least one aqueous phase comprising iii) at least one chitosan, at least one C, 6 carboxylic acid of formula (Q), having a pKa of less than 5, preferably lactic acid, and water. c. at least one coloring agent iv) chosen from pigments.
[0536] According to this preferred embodiment, the fatty phase preferably comprises at least one compound of formula (I) i) chosen from compounds (4) and (11) as well as their salts, isomers and solvates; and ii) at least one fatty acid comprising from 14 to 20 carbon atoms.
[0537] Preferably, the composition according to the invention comprises: a. a content ranging from 0.5 to 50% by weight, preferably ranging from 0.5 to 15% by weight, relative to the total weight of the composition, of a fatty phase comprising at least one compound of formula (I) as well as its optical, geometric and / or solvated isomers, such as hydrates, as defined previously, and at least one fatty acid, preferably at least one liquid fatty acid, b. a content ranging from 40 to 99% by weight, more preferably a content ranging from 80 to 99% by weight, relative to the total ratio of said composition, of an aqueous phase comprising:
[0538] water in a content ranging from 70 to 99% by weight, relative to the total weight of the aqueous phase,
[0539] chitosan, in a content ranging from 0.5 to 15% by weight, relative to the total weight of the aqueous phase, and
[0540] at least one organic acid, preferably at least one C1-C6 carboxylic acid of formula (Q), as defined above, having a pKa of less than 5, in a content ranging from 0.5 to 15% by weight, relative to the total weight of the aqueous phase a. at least one pigment in a total content ranging from 0.05 to 20% by weight, preferably ranging from 0.1 to 15% by weight, better still from 0.5 to 10% by weight relative to the total weight of the composition.
[0541] Preferably, the composition according to the invention comprises: a. a content ranging from 0.5 to 50% by weight, preferably ranging from 0.5 to 15% by weight, relative to the total weight of the composition, of a fatty phase comprising at least one compound chosen from compounds (1), (2), (3), (4), (7), (8), (9) and (11) in particular compounds (4) and (11) as described above, as well as their salts, isomers and solvates; and at least one liquid fatty acid corresponding to the structure Rioo-C(O)OH with RiOo corresponding to an alkyl group comprising from 14 to 20 carbon atoms, b. a content ranging from 40 to 99% by weight, more preferably a content ranging from 80 to 99% by weight, relative to the total ratio of said composition, of an aqueous phase comprising:
[0542] water in a content ranging from 70 to 99% by weight, relative to the total weight of the aqueous phase,
[0543] chitosan, in a content ranging from 0.5 to 15% by weight, relative to the total weight of the aqueous phase, and
[0544] at least one organic acid, preferably at least one C1-C6 carboxylic acid of formula (Q), having a pKa of less than 5 in a content ranging from 0.5 to 15% by weight, relative to the total weight of the aqueous phase, a. at least one pigment in a total content ranging from 0.05 to 20% by weight, preferably ranging from 0.1 to 15% by weight, better still from 0.5 to 10% by weight relative to the total weight of the composition. A. Process for preparing the composition
[0545] The composition according to the invention can be prepared by a process known to the person skilled in the art. More particularly, the process for preparing the oil-in-water emulsion comprises: a. the preparation, in a first container, of an aqueous solution of iii) at least one chitosan as defined previously; the aqueous solution of at least one chitosan further comprising at least one acid having a pKa of less than 5 as defined previously, b. the preparation, in a second container, of a mixture comprising at least one compound of formula (I), its optical, geometric and / or solvate isomers, such as hydrates, as defined above, and at least one fatty acid ii) as defined above, c. adding the mixture obtained in step b) to the aqueous solution obtained in step a) under controlled mechanical stirring.
[0546] An example of a method may consist of firstly solubilizing at least one chitosan iii) in water, in the presence of at least one acid with a pKa of less than 5, with stirring at a temperature which may vary from 20 to 45°C. An aqueous solution of chitosan is thus obtained.
[0547] In a thermostatically controlled tank and with controlled mechanical stirring, for example using a rotor / stator, at least one compound of formula (I) i), as described above, and at least one fatty acid ii) are mixed, preferably at room temperature (20°C) with stirring, until the fatty acid is dissolved.
[0548] The mixture comprising at least one compound of formula (I) i) and at least one fatty acid ii) is then added slowly to the aqueous chitosan solution maintained under mechanical stirring at room temperature, for example under mechanical stirring at 2000 rpm at the rotor / stator for a period of 10 minutes.
[0549] The pigment(s) may be dispersed in the resulting composition just before application.
[0550] The possible additive(s), as described above, is or are added to the aqueous phase and / or the fatty phase before emulsification.
[0551] Preferably, the additive(s) comprise glycerin. A. Process for treating keratin fibers
[0552] As indicated above, the invention also relates to a process for the cosmetic treatment of keratin fibers, preferably human fibers such as hair.
[0553] Preferably, the composition according to the invention is applied to dry or wet keratin fibers.
[0554] Preferably, the process for cosmetic treatment of keratin fibers, comprising at least the application to said keratin fibers, of at least one composition, in the form of an oil-in-water emulsion, as defined above, comprising at least one pigment.
[0555] Preferably, the compound(s) of formula (I) is or are chosen from compounds (1), (2), (3), (4), (7), (8), (9) and (11), in particular compounds (4) and (11) as described above, as well as their optical, geometric and / or solvated isomers, such as hydrates.
[0556] Preferably, the application step may be followed by at least one drying step.
[0557] Preferably, the treatment method is a method for coloring keratin fibers, in particular human keratin fibers, such as hair, comprising at least the application to said fibers of at least one composition, as defined above, comprising at least one pigment.
[0558] Preferably, the compound(s) of formula (I) is or are chosen from compounds (4) and (11) as described above, as well as their optical, geometric and / or solvated isomers, such as hydrates.
[0559] The composition can be applied to keratin fibers, light or dark, natural or colored, permed, bleached or straightened, dry or wet.
[0560] The step of applying the composition according to the invention may optionally be followed by a rinsing step. Preferably, the step of applying the composition according to the invention is followed by a rinsing step. A. Use
[0561] The present invention also relates to the use of at least one composition, as defined above, for the cosmetic treatment of keratin fibers, preferably human keratin fibers such as hair.
[0562] Preferably, the compound(s) of formula (I) is or are chosen from compounds (1), (2), (3), (4), (7), (8), (9) and (11), in particular compounds (4) and (11) as described above, as well as their optical, geometric and / or solvated isomers, such as hydrates.
[0563] Preferably, the invention also relates to the use of said composition for the treatment, preferably the coloring, of keratin fibers, in particular human keratin fibers, such as hair.
[0564] Even more preferably, the invention relates to the use of said composition for coloring keratin fibers, in particular human keratin fibers, such as hair, as defined above, comprising at least one pigment.
[0565] The following examples serve to illustrate the invention without, however, being limiting in nature. Examples
[0566] Synthesis of compound No. 4 belonging to formula (I):
[0567] The synthesis is represented by the following preparation scheme:
[0569] 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 a period of 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 a period of one hour.
[0570] Synthesis of compound No. 11 belonging to formula (I):
[0571] The synthesis is represented by the following preparation scheme: Step a): Step b):
[0574] During step a), in a 250 mL round-bottomed flask equipped with magnetic stirring, 100 g of castor oil (sold by Interchimie), 17 g of 3-Mercapto-1,2-propanediol (sold by Sigma Aldrich) and 1 g of 2-Hydroxy 2-methylpropiophenone (sold by Sigma Aldrich) are added to 20 mL of ethyl acetate and stirred for 5 minutes under argon. The reaction medium is then irradiated under a UV lamp (100 W, 365 nm) for 4 hours and then washed 3 times with saturated NaCl water. The organic phase is separated, dried over MgSO4, and then concentrated under vacuum. The solvent, traces of thiol and photoinitiator (2-Hydroxy 2-methylpropiophenone) are removed by distillation under reduced pressure.
[0575] In step b), 100 g of hydroxylated castor oil obtained in step a) and 99 g of tert-butyl acetoacetate are introduced into a 250 ml flask equipped with magnetic stirring. The reaction medium is then heated to a temperature of 130°C using an oil bath (setpoint 140°C on the oil bath). After a period of 4 hours, the reaction medium is placed under continuous vacuum for 1 hour. A viscous yellow oil is obtained. Compounds tested:
[0576] The formulations illustrated in the following examples were notably prepared with the following ingredients: - compound No. 4 prepared in accordance with the synthesis process described previously, - compound No. 11 prepared in accordance with the synthesis method described above, - oleic acid as a fatty acid, - chitosan sold under the trade name Kiosmetine - CSH (chitosan according to the invention - amino compound 1), - lactic acid as an acid with a pKa less than 5, - red iron oxide, CI 77491 as a pigment, - glycerin as an additive.
[0577] I. Preparation of the tested compositions 1. Preparation of the aqueous phase containing chitosan
[0578] An aqueous chitosan solution was prepared by diluting a 9% by weight concentrated chitosan acid solution and 5.8% by weight lactic acid. The required amount of solution is taken and diluted with distilled water to achieve the desired chitosan concentration in the aqueous phase. 1. Formulation of the emulsion
[0579] In a beaker, a mixture of compound of formula (I) and oleic acid was prepared under magnetic stirring until the oleic acid was dissolved.
[0580] The aqueous chitosan solution, prepared previously, is placed under controlled mechanical stirring at 500 rpm using a rotor / stator and at room temperature (20°C).
[0581] The mixture of compound of formula (I) and oleic acid is then slowly introduced into the aqueous phase with stirring at 2000 rpm on the rotor / stator for a period of 10 minutes.
[0582] An oil-in-water emulsion having a whitish appearance is then obtained. 1. Compositions (oil-in-water emulsions) obtained
[0583] The oil-in-water emulsions according to the protocol described in sections 1.1 and 1.2 from the ingredients previously described are indicated in the following table 1; the quantities are indicated in percentage by weight, unless otherwise indicated:
[0584] [Tables 1] Compositions 2 3 4 5 6 Compound (11) - 5 5 5 5 Compound (4) 5.7 - - - - Chitosan - amino compound 1 (invention) 4.01 4.75 4.75 4.75 4.75 Oleic acid 1.00 1.19 1.19 1.19 4.75 Lactic acid 2.56 3.04 3.04 3.04 3.04 Red iron oxide, CI 77491 8 8 16 8 8 Glycerin 0 0 0 5 0 Water (total weight in water supplemented) 100 100 100 100 100 1. Comparative compositions
[0585] Two additional comparative compositions (CCI and CC2) were also implemented and are described in the following Table 2:
[0586] [Tables2] CCI CC2 Compositions Compound (4) - 5.7 Compound (11) - - Non-functionalized castor oil (not part of the invention) 5.7 - Chitosan - amino compound 1 (invention) 4.01 4.01 Oleic acid 1.00 - Lactic acid 2.56 2.56 Red iron oxide, CI 77491 8 8 Water (total weight in water supplemented) 100 100
[0587] The comparative composition CCI is an oil-in-water emulsion comprising a non-functionalized castor oil (i.e. a compound not comprising an acetoacetate function belonging to formula (I) according to the invention).
[0588] Comparative composition CC2 comprises a compound (4), belonging to formula (I) according to the invention (i.e. oil with acetoacetate functions), but is not an emulsion.
[0589] Indeed, the comparative composition CC2 was obtained by mixing the ingredients listed in Table 2 without emulsification (i.e. in the absence of oleic acid and in the absence of mechanical stirring at 2000 rpm).
[0590] III. Evaluation of persistence to shampoos
[0591] The compositions described above are applied to locks of 90% white (90% BN) natural hair, at a rate of 1g of composition per gram of hair, then after application the lock of hair is dried using a hair dryer.
[0592] The locks of hair thus colored are then subjected to a test of several repeated shampoos (5 shampoos) in order to evaluate the tenacity (the persistence) of the coloring obtained from the shampoos.
[0593] The shampoo resistance evaluations are thus carried out 24 hours after the application of the composition to the lock of hair. Remanence protocol:
[0594] The color remanence of the wicks was evaluated in the CIE L*a*b* system, using a colorimeter (illuminant D65, angle 10°, specular component included).
[0595] In this L*a*b* system, L* represents the color intensity, a* indicates the green / red color axis and b* the blue / yellow color axis.
[0596] The color difference AE between the colored strands is calculated with the L*a*b* values before shampooing (hair after coloring) and after having undergone five shampoos via the equation below.
[0597] The value of AE is calculated according to the following equation: ae =
[0598] In this equation, L*a*b* represent the values measured after coloring the hair and after having undergone shampoos (colored hair having undergone 5 shampoos), and Lo*ao*bo* represent the values measured on the strand after coloring and before shampooing (colored hair before shampooing). Comparison of composition 2 and CCI composition:
[0599] The results of the evaluations are summarized in Tables 3 and 4 below:
[0600] [Tables3] CCI L* a* b* AE 0 shampoo 30.07 21.99 14.80 21.01 5 shampoos 49.53 14.47 17.33
[0601] [Tables4] Composition 2 L* a* b* AE 0 shampoo 33.73 28.38 22.39 8.27 5 shampoos 41.42 25.50 21.39
[0602] The results show that composition 2, in accordance with the invention, comprising at least one compound of formula (I) significantly improves the persistence of the coloring to shampoos compared to a CCI composition. Comparison of composition 2 and composition CC2:
[0603] The results of the evaluations of the persistence to shampoos of the comparative composition CC2 and the composition according to the invention 2 are summarized in tables 5 and 6 below:
[0604] [Tables5] CC2 L* a* b* AE 0 shampoo 29.00 24.75 17.14 30.47 5 shampoos 56.24 11.15 15.91
[0605] [Tableauxô] Composition 2 L* a* b* AE 0 shampoo 33.73 28.38 22.39 8.27 5 shampoos 41.42 25.50 21.39
[0606] The results show that composition 2, in accordance with the invention, in the form of an oil-in-water (O / W) emulsion, significantly improves the persistence of the coloring when shampooed compared to a non-emulsified composition CC2. Comparison of composition 5 and composition 3
[0607] The results of the evaluations of the persistence to shampoos of the composition according to the invention 5 and the composition according to the invention 3 are summarized in tables 9 and 10 below:
[0608] [Tables9] Composition 5 L* a* b* AE 0 shampoo 34.69 26.63 20.91 5.93 5 shampoos 39.23 23.35 18.97
[0609] [TableauxlO] Composition 3 L* a* b* AE 0 shampoo 34.13 25.92 19.93 9.21 5 shampoos 42.00 21.43 18.23
[0610] The results show that composition 5, in accordance with the invention, comprising an additive, in particular glycerin, in the aqueous phase makes it possible to improve the persistence to shampoos compared to a similar composition not comprising such an additive.
Claims
1. Claims Composition in the form of an oil-in-water emulsion comprising: - one or more compounds of formula (I), as well as its optical, geometric and / or solvated isomers, such as hydrates: (I) [(O^Kl)c^ 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 their combinations; - 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-; - R4 represents a monovalent C1 to C6 hydrocarbon radical, linear or branched, saturated or unsaturated, preferably a (CrC4)alkyl group, in particular methyl or tert-butyl, more preferably methyl;
2.
3. - Ra and Rb, identical or different, represent a hydrogen atom or a (Ci-C4)alkyl group, preferably a hydrogen atom; - p denotes an integer equal to 0 or 1; - m denotes an integer equal to 0, 1, 2, 3 or 4; it being understood that when m is greater than 1, then the radicals -Y-AK2 are identical or different; - n denotes an integer equal to 0, 1, 2, 3 or 4; it being understood that when n is greater than 1, then the radicals -(O)t-(AKi)q-(OC(O)-C(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; ii) one or more fatty acids, iii) at least chitosan, and iv) optionally one or more pigments v) optionally one or more fatty substances different from the fatty acid(s) ii). Composition according to claim 1, characterized in that the chitosan has a degree of acetylation less than or equal to 30%, preferably less than or equal to 15%, more preferably a degree of acetylation varying from 1 to 10%. Composition according to claim 1 or 2, characterized in that the compound(s) of formula (I), as well as their optical, geometric and / or solvated isomers, such as hydrates, are such that: - Z represents the trivalent radical -CH2-CH-CH2-; - p is equal to 0; - n is equal to 0; - m is equal to 3; - AK2 represents a linear or branched, saturated or unsaturated monovalent hydrocarbon chain, C12-C24, optionally substituted by one or more identical or different radicals chosen from -OR, -X-AK3-(OC(O)-C(Ra)(Rb)-C(O)-R4)v, and / or said chain being optionally interrupted by one or more heteroatoms or groups chosen from -O-, -S-, -C(O)-, epoxides, and combinations thereof, in particular particular -O(CO)- or -C(O)-O-; - Y, AK3, v, R, X, R4, Ra and Rb being as defined according to claim 1; it being understood that the compounds contain at least 2 radicals -C(O)-C(Ra)(Rb)-C(O)-R4.
4. Composition according to any one of the preceding claims, characterized in that the compound(s) of formula (I), as well as their optical, geometric and / or solvated isomers, such as hydrates, are such that: - 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 -(O)t-(AKi)q-(OC(O)-C(R a)(Rb)-C(O)-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 according to claim 1; it being understood that said compound contains at least 2 radicals -C(O)-C(Ra)(Rb)-C(O)-R4.
5. Composition according to any one of the preceding claims, characterized in that the compound(s) of formula (I), as well as their optical, geometric and / or solvated isomers, such as hydrates, are such that: - p is equal to 0; - n + m is equal to 4, m being non-zero; - Z represents a tetravalent, C2 to C24, particularly C3 to C10, in particular C3, unsubstituted and uninterrupted, linear or branched, saturated or unsaturated, preferably saturated and acyclic hydrocarbon radical; - AK2 independently represents a linear or branched, saturated or unsaturated, preferably saturated, monovalent hydrocarbon chain in C12-C24, preferably in 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 their combinations, in particular -OC(O)-, -C(O)-O-, -(hetero)cycle-O-(hetero)cycle-, and preferably being uninterrupted; - AK3 represents a linear or branched divalent hydrocarbon chain saturated or unsaturated in C1-C12, preferably in C1-C6, more preferably saturated in C1-C6, even more preferably in C2-C4, better still in C3; - v is as defined in claim 1; preferably v is equal to 2; - X is as defined in claim 1; preferably X denotes a sulfur atom; - Y, AK1, u, t, q, R, R4, Ra and Rb are as defined according to claim 1; it being understood that said compound contains at least 2 radicals -C(O)-C(Ra)(Rb)-C(O)-R4.
6. Composition according to any one of the preceding claims, characterized in that the compound(s) of formula (I), as well as their optical, geometric and / or solvated isomers, such as hydrates, are such that: - p is equal to 1; - Z represents a multivalent hydrocarbon radical from C1 to C24, particularly from C16 to C20, preferably Cp, linear or branched, saturated or unsaturated, preferably saturated and acyclic; Z being further optionally substituted by one or more radicals -[(O)t-(AKl)q -(OC(O)-C(Ra)(Rb)-C(O)-R4)u]n, preferably being unsubstituted; - AK2 represents a linear or branched, saturated or unsaturated, preferably saturated, monovalent hydrocarbon chain, C14-C30, of preferably C20-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 -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-, preferably being interrupted by -OC(O)- or -C(O)-O-; - X is as defined in claim 1, preferably X denotes a sulfur atom; - Y, AK1, AK3, n, m, v, t, q, u, R, R4, Ra and Rb being as defined in claim 1, it being understood that said compound contains at least 2 radicals C(O)-C(R a)(Rb)-C(O)-R4.
7. Composition according to any one of the preceding claims, characterized in that the compound(s) of formula (I), as well as their optical, geometric and / or solvated isomers, such as hydrates, are such that: - 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 not conjugated, acyclic or cyclic, aromatic or not, preferably not aromatic, said radical Z being further interrupted by one or more heteroatoms or groups chosen from -O-, -N(Ra)-, -S-, -C(O)-, heterocycloalkyl(s) comprising 5 or 6 links, and combinations thereof; - AK2 represents a linear or branched, saturated or unsaturated, preferably saturated, monovalent hydrocarbon chain of C14-C30, preferably C[4-C24, preferably Cp, said chain being optionally substituted by one or more identical or different radicals chosen from -OR and -X-AKS-CO-CCOj-CCRaXRJ-CXOj-RJv, 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 in claim 1, and preferably X denotes a sulfur atom; - Y, AK1, AK3, v, t, q, u, R, R4, Ra and Rb being as defined in claim 1, it being understood that said compound contains at least 2 C(O)-C(R a)(Rb)-C(O)-R4 radicals.
8. Composition according to any one of the preceding claims, characterized in that the compound(s) of formula (I) are chosen from the following compounds of formula (Ia), as well as their optical, geometric and / or solvated isomers, such as hydrates: Z-(Y-AK2)3 (Ia) formula (Ia) in which: - Z represents -CH2-CH-CH2- ; - AK2 independently denote 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 and -X-AK3-(OC(O)-C(Ra)(Rb)-C(O)-R4)v; and / or said chain being optionally interrupted by one or more heteroatoms or groups chosen from -O-, -S-, -C(O)-, epoxides, and combinations thereof, in particular -OC(O)- and -C(O)-O-; - Y, AK3, v, R, X, IC, Ra and Rb being as defined in claim 1, preferably Y denotes -OC(O); it being understood that said compound contains at least 2 C(O)-C(R a)(Rb)-C(O)-R4 radicals.
9. Composition according to any one of the preceding claims, characterized in that the compound(s) of formula (I) are chosen from the following compounds of formula (Ib), as well as their optical, geometric and / or solvated isomers, such as hydrates: 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 in claim 1; - 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 monovalent hydrocarbon chain, preferably saturated or unsaturated saturated, 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)-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- or -(hetero)cycle-O-(hetero)cycle-, preferably being uninterrupted; - AK3 represents a linear or branched divalent hydrocarbon chain saturated or unsaturated in CrCi2, preferably in Ci-C6, more preferably saturated in Ci-C6, even more preferably in C2-C4, preferably in C3; - v is as defined in claim 1, preferably v is equal to 2; - X is as defined in claim 1, preferably X denotes a sulfur atom; - Y, AK1, t, q, R, R4, Ra and Rb being as defined in claim 1; it being understood that said compound contains at least 2 radicals -C(O)-C(Ra)(Rb)-C(O)-R4.
10. Composition according to any one of the preceding claims, characterized in that the compound(s) of formula (I) are chosen from the following compounds of formula (Ic), as well as their optical, geometric and / or solvated isomers, such as hydrates: m(AK2 -Y) - ZH - [(O)t-(AKl)q-(OC(O)-C(Ra)(Rb)-C(O)-R4)u]n (the) formula (the) in which: - Z represents a multivalent hydrocarbon radical 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 in claim 1, and preferably X denotes a sulfur atom; - Y, AK1, AK3, n, m, v, t, q, u, R, R4, Ra and Rb being as defined in claim 1; it being understood that said compound contains at least 2 radicals -C(O)-C(Ra)(Rb)-C(O)-R4.
11. Composition according to any one of the preceding claims, characterized in that the compound(s) of formula (I) chosen from the following compounds of formula (Id), as well as their optical, geometric and / or solvated isomers, such as hydrates: 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(Ra)(R b)-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 being uninterrupted; X is as defined in claim 1, preferably X denotes a sulfur atom; Y, AK1, AK3, v, R, IC, Ra and Rb being as defined in claim 1, it being understood that these compounds contain at least 2 radicals -C(O)-C(Ra)(Rb)-C(O)-R4.
12. Composition according to any one of the preceding claims, characterized in that the compound(s) of formula (I) are chosen from the following compounds of formula (Ic), as well as their optical isomers, geometric and / or solvated, such as hydrates: m(AK2-Y) - Z - [(0)t-(AKl)q-(0-C(0)-C(Ra)(Rb)-C(0)-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 in claim 1, preferably X denotes a sulfur atom; - Y, AK1, AK3, v, t, q, u, R, R4, Ra and Rb being as defined in claim 1; it being understood that said compound contains at least 2 C(O)-C(R) radicals
13. a)(Rb)-C(O)-R4. Composition according to any one of the preceding claims, characterized in that the compound(s) of formula (I) are chosen from the compounds below, as well as their optical, geometric and / or solvated isomers, such as hydrates: (8) (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) of formula (I) is or are chosen from compounds (4) and (11) as well as their optical isomers, geometric isomers and / or their solvates such as hydrates.
14. Composition according to any one of the preceding claims, characterized in that the fatty acid(s) is(are) chosen from compounds of structure R20-C(O)OH in which R20 represents a
15.
16.
17. hydrocarbon group, linear or branched, saturated or unsaturated, comprising from 5 to 30 carbon atoms, preferably from 7 to 29 carbon atoms, preferentially from 9 to 24 carbon atoms, better still from 11 to 19 carbon atoms, preferably the fatty acid(s) is or are chosen from lauric acid, myristic acid, palmitic acid, stearic acid, oleic acid, linoleic acid, arachidonic acid, isostearic acid, isopalmitic acid, and mixtures thereof, more preferentially oleic acid. Composition according to any one of the preceding claims, characterized in that it further comprises at least glycerin. Process for the cosmetic treatment of keratin fibers, in particular human keratin fibers such as hair, comprising at least the application to said fibers of at least one composition, as defined according to any one of claims 1 to 15. Process according to claim 16, characterized in that it is a process for coloring keratin fibers comprising at least the application to said fibers of at least one composition, as defined according to any one of claims 1 to 15, comprising one or more pigments.
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