A process for treating keratinous materials using at least one polyester compound with acetoacetate functional groups.

A treatment process using a polyester compound with acetoacetate functions addresses the limitations of existing cosmetic compositions by providing long-lasting, stable shine and resistance to water and oils on keratinous materials, while being environmentally friendly and comfortable.

FR3163569A1Pending Publication Date: 2025-12-26LOREAL SA
View PDF 42 Cites 0 Cited by

Patent Information

Application Number
FR2024006772
Authority / Receiving Office
FR · FR
Patent Type
Applications
Current Assignee / Owner
Filing Date
2024-06-24
Publication Date
2025-12-26

AI Technical Summary

Technical Problem

Existing cosmetic compositions fail to provide long-lasting, non-sticky, and stable shine on keratinous materials while being environmentally friendly, resistant to water and oils, and comfortable to wear, and do not meet consumer demands for natural and biodegradable ingredients.

Method used

A treatment process involving the application of a polyester compound with acetoacetate functions, optionally with a crosslinking agent, to keratinous materials, enhancing durability and shine while avoiding the need for an oily phase.

Benefits of technology

The process results in coatings that are resistant to external aggressions, provide high and stable shine, and are comfortable, non-sticky, and non-transferable, meeting consumer demands for natural and biodegradable ingredients.

✦ Generated by Eureka AI based on patent content.
Patent Text Reader

Abstract

Title: Process for treating keratinous materials using at least one polyester compound with acetoacetate functionalities. The present invention relates to a process for treating keratinous materials comprising applying to said keratinous materials, in one or more successive steps, at least: i) at least one polyester of formula (I) comprising at least two acetoacetate functionalities, as well as its optical, geometric, and / or solvate isomers, such as hydrates, or a composition containing it or them: (Z)–[OC(O)-C(Ra)(Rb)-C(O)-R4]u (I), formula (I) in which Z, u, R4, Ra, and Rb are as defined in the description, and ii) optionally, at least one crosslinking agent. Figure for the abstract: None
Need to check novelty before this filing date? Find Prior Art

Description

Title of the invention: Process for treating keratinous materials using at least one polyester compound with acetoacetate groups. Technical field

[0001] The present invention relates more particularly to the cosmetic field of keratin materials, and in particular to that of the care and / or makeup of the skin and / or lips and / or eyelashes and / or eyebrows, and that of the care, styling and / or coloring of keratin fibers and preferably of hair.

[0002] It aims to propose in particular new treatment processes, especially cosmetic ones, including the application on keratinous materials of a polyester compound with acetoacetate functions and possibly a crosslinking agent, which are particularly interesting with regard to their technical performance, especially in terms of the durability of the deposits and the qualities of shine that they make it possible to obtain. Previous technique

[0003] Cosmetic products classically require the implementation of one or more film-forming polymers in order to obtain a quality deposit of these products on keratinous materials, and in particular giving satisfaction to the expectations detailed below.

[0004] Thus, in the field of skin and / or lip makeup, it is particularly expected that the deposit formed will not transfer upon contact with fingers or clothing.

[0005] It must also exhibit good resistance to shine and good resistance to contact with water, particularly rain or during showering, as well as perspiration and sebum, and even to contact with food fats, particularly cooking oils when this deposit forms on the lips. Furthermore, this deposit must be comfortable.

[0006] For this purpose, it is used in makeup products, such as mascaras, eyeliners, eyeshadows or lipsticks, and in hair application products, and more particularly in their organic and especially oily phases, as dispersions of nanometric polymer particles, as a film-forming agent.

[0007] However, the compositions of the prior art show a durability over time, in particular of the hairstyle, which is not always satisfactory.

[0008] As for shine, it is generally obtained by formulating shine oils, such as polybutenes, which are characterized by their nonpolar nature. However, this type of oil has a low capacity to disperse pigments. Similarly, cosmetic compositions containing one or more shine oils may exhibit color retention over time that is not entirely satisfactory from a cosmetic standpoint, such as lasting less than 4 hours, or even less than 1 hour. These oils also have the disadvantage of being sticky and providing only a short-lived shine, less than 1 or 2 hours, for example. Finally, compositions incorporating these oils can migrate into wrinkles and fine lines and may generate an unsightly effect that is detrimental to their use by consumers.

[0009] In addition, the formulation of environmentally friendly cosmetic products, that is to say, whose design and development take into account environmental issues, is becoming a major concern in order to help meet global challenges.

[0010] It is therefore essential to propose more sustainable compositions and / or preparation processes and / or ingredients, thus enabling us to meet these environmental challenges.

[0011] Alkyd resins provide interesting properties in applications cosmetics. Furthermore, these resins can be fully or partially bio-based, and some are biodegradable. However, these alkyd resins have a major drawback: they are sensitive to common cosmetic irritants such as oils, like olive oil or sebum, and / or water, and are even prone to fragmentation, which limits their suitability for application on keratinous materials.

[0012] The use of polycondensates, also referred to hereinafter as polyesters, as an alternative or complement to gloss oils, as described for example in EP 1 870 082, has made it possible to partially overcome the aforementioned drawbacks, in particular by providing access to compositions with, on the one hand, improved gloss resulting in greater shine and a wet look and, on the other hand, good retention of this gloss over time, particularly after a few hours, and especially beyond 4 hours. However, it would be desirable to be able to enhance the effectiveness of these compositions in terms of color retention, particularly over time and especially after a meal, and in terms of gloss retention over time.

[0013] There is also significant consumer demand for the use of more natural compositions, implementing compounds of natural origin possibly modified.

[0014] In this context, it is important to develop processes for preparing cosmetic products and / or cosmetic ingredients with a better carbon footprint capable of reducing the generation of carbon dioxide throughout the product life and / or low cost in energy and water and / or using greener solvents and / or with fewer synthesis steps and / or with good atom economy.

[0015] Furthermore, in the field of hair care, a new range of products called hair makeup or "Hair Make-up" has recently been developed. These products guarantee temporary hair coloring that lasts after 1 to 3 shampoos.

[0016] They therefore constitute an alternative, particularly attractive for consumers, to permanent coloring, provided of course that the color effect is effectively guaranteed to hold up in contact with water and a few shampoos.

[0017] This requirement is also met in particular through the implementation of effective film-forming agents.

[0018] Thus, documents WO2003089494 and WO2003087192 propose acetoacetate functionalized alkyd resins capable of undergoing crosslinking as a film-forming agent, which can be used to prepare industrial coatings with a low VOC content.

[0019] In general, the processes and treatments described above do not allow access to deposits, both on keratin fibers and on skin and lips, which satisfy all the aforementioned requirements, namely very good resistance to water, in particular to shampoos for hair, and / or to oils, especially for lips, which are also comfortable for users to wear, and a high and stable shine over time, and which, in the case of hair use, provide very satisfactory hold of styling or colonic persistence while meeting the need for naturalness, bio-sourced and / or biodegradability expressed by some consumers and / or formulations where the presence of an oily phase is not desired. Description of the invention

[0020] There therefore remains a need for a treatment process, particularly cosmetic, intended for application on the skin which allows obtaining a non-sticky deposit, which transfers little or not at all, shiny, comfortable, long-lasting and whose implementation does not necessarily require the presence of an oily phase, while being of natural origin.

[0021] There also remains a need for a treatment process, particularly cosmetic, to obtain deposits that are resistant to water and grease, especially sebum.

[0022] There also remains a need for a treatment process, particularly cosmetic, to provide deposits with high gloss qualities.

[0023] There also remains a need for a treatment process, particularly cosmetic, coloring and intended for hair application, which provides deposits with good resistance to water and shampoos to guarantee color retention over time comparable to direct coloring.

[0024] There is also a need for a treatment process, in particular cosmetic, in particular non-coloring, intended for hair application which provides styling properties, in particular curl retention, resistant to water.

[0025] The present invention is specifically designed to meet all or part of these needs. Summary of the invention

[0026] These problems are solved by implementing a process for treating keratinous materials, comprising applying to said keratinous materials, in one or more successive steps, at least: (i) at least one polyester of the following formula (I) comprising at least two acetoacetate functions, as well as its optical, geometric and / or solvated isomers, such as hydrates, or a composition containing it or them: (Z)-[OC(O)-C(Ra)(Rb)-C(O)-R4]u(I) formula (I) in which: - Z denotes a multivalent radical derived from: of an alkyd resin (A) obtained by reaction: - from 10% to 62% mass of at least one polyol; - from 10% to 62% mass of at least one polyacid; - 35% to 60% by mass of at least one fatty alcohol and / or at least one monoacid bold; and - from 0% to 20% by mass of at least one monocarboxylic acid; mass percentages being expressed in relation to the total weight of the alkyd resin (A); Or of an alkyd resin (B) resulting from the reaction of an alkyd resin (A) containing ethylenic unsaturations with at least one (poly)hydroxy thiol; - u is an integer greater than 2; - R4 represents a monovalent hydrocarbon radical in C1 to C6, linear or branched, saturated or unsaturated, preferably a (Ci-C4)alkyl group, in particular methyl or tert-butyl, more preferably methyl; - Ra and Rb, identical or different, represent a hydrogen atom or a (Ci-C4)alkyl group, preferably a hydrogen atom; and ii) possibly, at least one crosslinking agent.

[0027] According to a preferred embodiment, the treatment process according to the invention comprises the application of at least ii) a crosslinking agent.

[0028] According to a preferred embodiment, the treatment process according to the invention further comprises the application of at least iv) a cosmetic active ingredient, on said keratinous materials.

[0029] According to a preferred embodiment, the process according to the invention comprises the application i) of at least one polyester of formula (I), its optical, geometric isomers, its acid or base salts, and / or its solvates, such as hydrates, or of a composition containing it or them, optionally the application ii) of at least one crosslinking agent, and the application iv) of at least one cosmetic active ingredient, on said keratin materials.

[0030] According to one embodiment, the process includes the application of i), optionally ii) and optionally iv) to moist or wet keratinous materials.

[0031] The inventors have thus surprisingly observed that applying ingredients i), and optionally ii), and iv), to keratinous materials produces coatings on the skin that exhibit good resistance to external aggressions such as water, oils (particularly cooking oils), sweat, and / or sebum, displaying a high and stable shine over time, and therefore possessing very good durability. Advantageously, the coatings obtained with the processes according to the invention are also very comfortable. They are non-sticky and non-transferable. Applying ingredients i), and optionally ii), and iv), to keratinous materials also produces coatings on keratinous fibers that exhibit good resistance to shampoos and water.

[0032] The application of ingredients i), and optionally ii), and iv), to keratinous materials also makes it possible to obtain deposits of very high and lasting gloss. Definitions

[0033] For the purposes of the present invention, and unless otherwise indicated:

[0034] - by "multivalent" we mean a radical that is at least divalent; the valence of the radical Ri is equal to n as defined previously, the radical Ri thus being "n-valent". As an example, when n is equal to 3, the radical Ri is trivalent;

[0035] - For the purposes of this invention, "keratinous materials" means to designate including the lips, skin, nails and keratin fibers, in particular eyelashes, eyebrows and hair, preferably the lips and / or hair.

[0036] - By "cosmetic active ingredient": we mean an organic or organosilicon compound, or a A mineral compound that can be incorporated into a cosmetic composition to have an effect on keratinous materials, whether this effect is immediate or achieved through repeated applications. Examples of cosmetic active ingredients include colored or non-colored, fluorescent or non-fluorescent compounds such as optical brighteners, or UVA and / or UVB filters; anti-aging actives or those intended to benefit the skin, such as those acting on the skin barrier function, deodorant actives, antiperspirant actives, desquamating actives, antioxidant actives, moisturizing actives, sebum-regulating actives, actives intended to combat the effects of pollution, antimicrobial or bactericidal actives, perfumes, and coloring materials such as direct dyes or pigments, preferably pigments.

[0037] Preferably, the cosmetic actives are chosen from a) colouring materials chosen from pigments, direct colorants, and their mixtures, b) care actives for keratinous materials, preferably of the skin, c) UV filters, and d) their mixtures.

[0038] - For the purposes of this invention, "fatty body" means a compound organic insoluble in water at ordinary temperature (25 °C) and atmospheric pressure (760 mm Hg) (solubility less than 5%, and preferably 1%, even more preferably 0.1%); in addition, fats are soluble in organic solvents under the same conditions of temperature and pressure, such as halogenated solvents like chloroform, dichloromethane, inferior alcohols like ethanol or aromatic solvents like benzene or toluene.

[0039] - By "alkyl" we mean a saturated hydrocarbon radical, linear or branched.

[0040] - By "a (Cx-Cy)alkyl group" is meant an alkyl radical comprising x to y carbon atoms.

[0041] - By "(hetero)aryl" we mean the aryl or heteroaryl groups.

[0042] - By "(hetero)cycloalkyl" we mean cycloalkyl or heterocycloalkyl groups.

[0043] - The "aryl" or "heteroaryl" radicals or the aryl or heteroaryl part of a radicals can be substituted by at least one substituent attached to a carbon atom, chosen from: - a CrC6 (poly)(hydroxy)alkyl radical, preferably in C1-C4; - a halogen atom such as chlorine, fluorine or bromine; - a hydroxy group; - a C1-C2 alkoxy radical; a C2-C4 (poly)-hydroxyalkoxy radical; - an amino radical; - an amino radical substituted by one or two alkyl radicals, identical or different, in Ci-C6, Ci-C6, preferably in CrC4; - an acylamino radical (-N(R)-C(O)-R') in which the radical R is a hydrogen atom, - an alkyl radical in CrC4 and the radical R' is an alkyl radical in CrC4; a carbamoyl radical ((R)2N-C(O)-) in which the radicals R, identical or not, represent a hydrogen atom, an alkyl radical in CrC4; - an alkylsulfonylamino radical (R'-S(O)2-N(R)-) in which the radical R represents a hydrogen atom or an alkyl radical in CrC4 and the radical R' represents an alkyl radical in Ci-C4 or a phenyl radical; - an aminosulfonyl radical ((R)2N-S(O)2-) in which the R radicals, identical or not, represent a hydrogen atom, an alkyl radical in CrC4; - a carboxylic radical in acidic or salified form (preferably with an alkali metal or an ammonium, substituted or unsubstituted); - a cyano group (CN); - a polyhalogeno(Ci-C4)alkyl group, preferably trifluoromethyl (CF3).

[0044] - The cyclic or heterocyclic part of a non-aromatic radical can be substituted by at least one substituent on a carbon atom chosen from the following groups: - hydroxy, - alkoxy in Ci-C4, (poly)hydroxyalkoxy in C2-C4, - alkylearbonylamino ((RC(O)-N(R')-) in which the radical R' is a hydrogen atom, an alkyl radical in CrC4 and the radical R is an alkyl radical in CrC2, amino substituted by one or two identical or different alkyl groups in CrC4; - alkylearbonyloxy ((RC(O)-O-) in which the radical R is an alkyl radical in CrC4, amino substituted by one or two identical or different alkyl groups in CrC4; - alkcoxycarbonyl ((ROC(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;

[0045] - A cyclic radical, heterocyclic radical, or a non-aromatic part of a radical aryl or heteroaryl, can also be substituted by one or more oxo groups.

[0046] - A hydrocarbon chain is unsaturated when it comprises one or more double bonds and / or one or more triple bonds, which may or may not be conjugated.

[0047] - An "aryl" radical represents a mono- or polycyclic group hydrocarbon, condensed or not, comprising from 6 to 14 carbon atoms, and of which at least one ring is aromatic; preferably the aryl radical is a phenyl, biphenyl, naphthyl, indenyl, anthracenyl, or tetrahydronaphthyl.

[0048] - A "heteroaryl" radical represents a mono- or polycyclic group, condensed or not, comprising 5 to 14 links, 1 to 6 heteroatoms chosen from nitrogen, oxygen, sulfur and selenium atoms, and of which at least one ring is aromatic; preferably a heteroaryl radical is chosen from acridinyl, benzimidazolyl, benzobistriazolyl, benzopyrazolyl, benzopyridazinyl, benzoquinolyl, benzothiazolyl, benzotriazolyl, benzoxazolyl, pyridinyl, tetrazolyl, dihydrothiazolyl, imidazopyridinyl, imidazolyl, indolyl, isoquinolyl, naphthoimidazolyl, naphthooxazolyl, naphthopyrazolyl, oxadiazolyl, oxazolyl, oxazolopyridyl, phenazinyl, phenooxazolyl, pyrazinyl, pyrazolyl, pyrilyl, pyrazoyltriazyl, pyridyl, pyridinoimidazolyl, pyrrolyl, quinolyl, tetrazolyl, thiadiazolyl, thiazolyl, thiazolopyridinyl, thiazoylimidazolyl, thiopyrylyl, triazolyl, xanthylyl.

[0049] - A "cyclic" or "cycloalkyl" radical is a non-cyclic hydrocarbon radical aromatic, mono- or polycyclic, condensed or non-condensed, containing from 5 to 14 carbon atoms, which may have from 1 to several unsaturations, preferably the cycloalkyl is a cyclohexyl group.

[0050] - A "heterocyclic" or "heterocycloalkyl" radical is a non-cyclic radical aromatic mono or polycyclic, condensed or non-condensed, containing 3 to 9 links, comprising 1 to 4 heteroatoms chosen from nitrogen, oxygen, sulfur and selenium atoms, preferably the heterocycloalkyl is chosen from epoxide, piperazinyl, piperidinyl, morpholinyl, or dithiolane.

[0051] - An "alkyl" radical is a saturated hydrocarbon radical, linear or branched, in particularly in Ci-C6, preferably in CrC4.

[0052] - An "alkoxy" radical is an alkyl-oxy radical in which the alkyl radical is a hydrocarbon radical, linear or branched, in Ci-C6 preferentially in CrC4.

[0053] - A "(poly)(hydroxy)alkyl" radical designates a Ci-C6 alkyl radical, of preferably in Ci-C4 possibly substituted by one or more hydroxy radicals, preferably substituted by 1 to 4 hydroxy groups, more particularly between 1 and 3.

[0054] - By "polyvalent radical", we mean a radical that is at least divalent, such as a radical divalent, trivalent or tetravalent, preferably divalent or trivalent.

[0055] - By "anionic counterion" is meant an anion or anionic group associated with the cationic charge; more particularly the anionic counter-ion is chosen from i) halides such as chloride, bromide; ii) nitrates; iii) sulfonates including the Ci-C6 alkylsulfonates: Alk-S(O)2O such as methylsulfonate or mesylate and ethylsulfonate; iv) arylsulfonates: Ar-S(O)2O such as benzenesulfonate and toluenesulfonate or tosylate; v) citrate; vi) succinate; vii) tartrate; viii) lactate; ix) alkyl sulfates: Alk-OS(O)O such as methyl sulfate and ethyl sulfate; x) aryl sulfates: Ar-OS(O)O such as benzene sulfate and toluene sulfate; xi) alkoxysulfates: Alk-OS(O)2O such as methoxysulfate and ethoxysulfate; xii) aryloxysulfates: Ar-OS(O)2 O, xiii) phosphate; xiv) acetate; xv) triflate; and xvi) borates such as tetrafluoroborate, their mixtures.- The "solvates" represent the hydrates as well as the association with linear or branched C2-C6 alcohols also called (C2-C6)alkanols such as ethanol, isopropanol, n-propanol.

[0056] - By "UV-A filter" is meant a chromophore derived from a compound that filters (or absorbs) UV-A ultraviolet rays at a wavelength between 320 and 400 nm. We can distinguish between short UV-A filters (absorbing rays at a wavelength between 320 and 340 nm), and long UV-A filters (absorbing rays at a wavelength between 340 and 400 nm).

[0057] - By "UV-B filter" is meant a chromophore derived from a compound that filters (or absorbs) ultraviolet UV-B rays at a wavelength between 280 and 320 nm.

[0058] - By "chromophore" is meant a radical derived from a colorless or colored compound capable of absorbing UV and / or visible radiation at a wavelength Xabs between 250 and 800 nm. Preferably, the chromophore is colored, i.e., it absorbs wavelengths in the visible range, i.e., preferably between 400 and 800 nm. Preferably, chromophores appear colored to the eye; particularly between 400 and 700 nm (Ullmann's Encyclopedia, 2005, Wiley-VcH, Verlag "Dies, General Survey", § 2.1 Basic Principle of Color).

[0059] - By "anhydrous composition" it is understood that said composition contains a quantity less than 5% by weight of water, preferably less than 3% by weight of water, better less than 1% by weight of water, relative to the total weight of the composition in question, even more preferably the composition in question is free of water.

[0060] - The terms "coloring agent" and "coloring matter" are equivalent.

[0061] Throughout the description, including the claims, the expression "comprising a" shall be understood as synonymous with "comprising at least one" or synonymous with "comprising one or more", unless otherwise specified.

[0062] - by "polycondensate" is meant a polyester resulting from the functionalization of a alkyd resin with acetoacetate functions.

[0063] - by "(co)polymer", we mean a homopolymer or a copolymer.

[0064] - by "homopolymer" is meant a polymer resulting from the repetition of units polymeric or monomers, of which said monomers are all identical, i.e. of the same chemical nature (for example -AAAA-...-AA-),

[0065] - by "copolymer" is meant a polymer resulting from the repetition of units polymeric or monomeric, of which at least two repeating monomers are different, i.e. of different chemical natures (for example -ABAA-...-BA-, it being understood that A is different from B); preferably, the (co)polymer(s) of the invention are copolymers.

[0066] The expressions "between ... and ...", "includes from ... to ...", "made up of ... to ...", and "ranging from ... to ..." should be understood inclusive of bounds, unless otherwise specified.

[0067] It is understood that the treatment processes according to the invention, as well as the compositions implemented, are non-therapeutic. Detailed description

[0068] METHOD FOR TREATMENT OF KERATINIC MATERIALS

[0069] The first object of the invention is a one- or multi-step treatment process comprising applying to keratinous materials, in particular keratin fibers or skin, at least: (i) at least one polyester of formula (I) comprising at least two acetoacetate functions, as well as its optical, geometric and / or solvated isomers, such as hydrates, or a composition containing it or them; ii) possibly at least one crosslinking agent, in particular as defined below; iv) possibly at least one cosmetic active ingredient, in particular as defined above and below; and (v) possibly at least one fat, in particular at least one oil, preferably volatile.

[0070] According to a particular embodiment of the invention, the treatment process according to the invention involves the simultaneous application of ingredients i), possibly ii), possibly iv) and possibly v).

[0071] According to another particular embodiment of the invention, the treatment process according to the invention comprises at least 2 sequential steps in which ingredients i) and ii) are applied separately to the keratin materials, it being understood that each of ingredients i) and ii) is optionally applied simultaneously with ingredient(s) iv) when present and / or with ingredient(s) v) when present.

[0072] According to a particular embodiment, ingredient(s) i) are applied to the keratin materials, then ingredient(s) ii) are applied to the keratin materials, if present, it being understood that ingredient(s) iv), when present, may be applied together with i) and / or with ii) and / or with v), when v) is present, and that ingredient(s) v), when present, may be applied together with i) and / or ii) and / or iv), preferably with i) and / or ii).

[0073] According to another particular embodiment, ingredient(s) ii) are applied to the keratin materials, then ingredient(s) i) are applied to the keratin materials, it being understood that ingredient(s) iv) when present may be found applied together with i) and / or ii), and that ingredient(s) v), when present, may be found applied with i) and / or with ii) and / or with iv), when iv) is present.

[0074] According to a particular embodiment of the invention, the process for treating keratinous materials is a process, in particular cosmetic, for treating keratinous materials, in particular for the care and / or makeup of the skin, lips, eyelashes and / or eyebrows and / or for the care, styling and / or coloring of keratinous fibers, preferably hair.

[0075] According to a particular embodiment of the invention, the process for treating keratinous materials is a cosmetic process for the care, styling and / or coloring of keratinous fibers, preferably hair.

[0076] According to another embodiment of the invention, the process for treating keratinous materials is a skin care process.

[0077] According to another embodiment of the invention, the process for treating keratinous materials is a process for applying makeup to the skin, lips, eyelashes, and eyebrows. According to this embodiment, the process comprises at least one cosmetic active ingredient selected from coloring materials, preferably pigments.

[0078] According to one aspect of the invention, the process for treating keratinous materials according to the invention implementing ingredients i), possibly ii), (possibly iv) and (possibly v), is a process for staining keratin fibers.

[0079] According to another aspect of the invention, the process for treating keratinous materials according to the invention implementing ingredients i), possibly ii), possibly iv) and possibly v), is a skin care process.

[0080] According to one embodiment of the invention, the process according to the invention is a process for treating, in particular cosmetically, keratinous materials, in particular for the care and / or makeup of the skin, lips, eyelashes and / or eyebrows and / or for the care, styling and / or coloring of keratinous fibers, preferably hair, comprising the application on said keratinous materials of at least: - i) at least one polyester of formula (I) comprising at least two acetoacetate functions as defined above and below, or a composition, referred to as "Cl", comprising i) at least one polyester of formula (I) as well as its optical, geometric isomers, its organic or mineral acid or base salts, and / or solvated, such as hydrates, as defined above and below, and optionally iv) at least one cosmetic active ingredient, in particular as defined above and below;Preferably, the composition "Cl" does not include ii) a crosslinking agent; - a composition, referred to as "C2", comprising i) at least one polyester of formula (I) as well as its optical, geometric isomers, its organic or mineral acid or base salts, and / or solvates, such as hydrates, as defined above and below, ii) at least one crosslinking agent, in particular as defined above and below, and optionally iv) at least one cosmetic active ingredient, in particular as defined above and below; preferably, the "C2" composition does not include iv) a cosmetic active ingredient; - a composition, referred to as "C3", comprising i) at least one polyester of formula (I) as well as its optical, geometric isomers, its organic or mineral acid or base salts, and / or solvates, such as hydrates, as defined above and below, ii) at least one crosslinking agent, in particular as defined above and below, and iv) at least one cosmetic active ingredient, in particular as defined above and below; - a composition, referred to as "C4", comprising ii) at least one crosslinking agent, in particular as defined above and below, and optionally iv) at least one cosmetic active ingredient, in particular as defined above and below; preferably, composition "C4" does not comprise i) at least one polyester of formula (I), its optical, geometric isomers, its organic or mineral acid or base salts, and / or solvates, such as hydrates, as defined above and below; and / or - a composition, referred to as "C5", comprising iv) at least one cosmetic active ingredient, in particular as defined above and below; preferably, composition " C5 does not include (i) at least one polyester of formula (I), its optical, geometric, acidic, or base salts, organic or mineral, and / or solvated, such as hydrates, as defined above and below, and does not include (ii) at least one crosslinking agent as defined above and below; provided that the process employs i) at least one polyester of formula (I) comprising at least two acetoacetate functions as defined above and below and that the compositions "Cl", "C2", "C3", "C4" and / or "C5" may comprise v) one or more fats, in particular at least one oil, preferably volatile as defined above and below, more preferably isododecane.

[0081] According to one embodiment of the invention, the process according to the invention is a treatment process, particularly for cosmetic purposes, of keratinous materials, especially for the care and / or makeup of the skin, lips, eyelashes and / or eyebrows and / or for the care, styling and / or coloring of keratinous fibers, preferably hair, comprising the application to said keratinous materials of i) at least one polyester of formula (I) comprising at least two acetoacetate functions as defined above and below, included in a composition, referred to as "Cl" comprising i), optionally iv) at least one cosmetic active ingredient, particularly as defined above and below; preferably, composition "Cl" does not include ii) a crosslinking agent; or - said polyester of formula (I) being included in a composition, referred to as "C2", comprising i), ii) at least one crosslinking agent, in particular as defined above and below, and optionally iv) at least one cosmetic active ingredient, in particular as defined above and below; preferably, composition "C2" does not comprise iv) any cosmetic active ingredient; or - said polyester of formula (I) being included in a composition, referred to as "C3", comprising i), ii) at least one crosslinking agent, in particular as defined above and below, iv) at least one cosmetic active ingredient, in particular as defined above and below, and preferably selected from coloring materials, preferably pigments, it being understood that the compositions "Cl", "C2" and / or "C3" may include (v) one or more fats, in particular at least one oil, preferably volatile as defined above and below, more preferably isododecane.

[0082] According to one embodiment of the invention, the process according to the invention is a treatment process, particularly for cosmetic purposes, of keratinous materials, especially for the care and / or makeup of the skin, lips, eyelashes and / or eyebrows and / or for the care, styling and / or coloring of keratinous fibers, preferably hair, comprising the application to said keratinous materials of i) to less a polyester of formula (I) comprising at least two acetoacetate functions as defined above and below, included in a composition, referred to as "C2", comprising i), ii) at least one crosslinking agent, in particular as defined above and below, and optionally iv) at least one cosmetic active, in particular as defined above and below; and optionally v) one or more fatty substances, in particular at least one oil, preferably volatile as defined above and below, more preferably isododecane; Preferably, the composition "C2" does not include iv) any cosmetic active ingredient.

[0083] According to one embodiment of the invention, the process according to the invention is a treatment process, particularly for cosmetic purposes, of keratinous materials, especially for the care and / or makeup of the skin, lips, eyelashes and / or eyebrows and / or for the care, styling and / or coloring of keratinous fibers, preferably hair, comprising the application to said keratinous materials of i) at least one polyester of formula (I) comprising at least two acetoacetate functions as defined above and below, included in a composition, referred to as "C3", comprising i), ii) at least one crosslinking agent, particularly as defined above and below, iv) at least one cosmetic active ingredient, particularly as defined above and below, preferably at least one coloring agent, more preferably at least one pigment, and optionally v) one or more fatty substances, particularly at least one oil,preferably volatile as defined above and below, more preferably isododecane.

[0084] According to one embodiment of the invention, the process according to the invention is a treatment process, particularly for cosmetic purposes, of keratinous materials, especially for the care and / or makeup of the skin, lips, eyelashes and / or eyebrows and / or for the care, styling and / or coloring of keratinous fibers, preferably hair, comprising the application to said keratinous materials of: (i) at least one polyester of formula (I) comprising at least two acetoacetate functions as defined above and below, included in a composition, referred to as "Cl", comprising (i), optionally (iv) at least one cosmetic active ingredient, in particular as defined above and below; preferably, composition "Cl" does not comprise (ii) a crosslinking agent; and (i) at least one crosslinking agent, in particular as defined above and below, included in a composition, referred to as "C4", comprising (ii) at least one crosslinking agent, in particular as defined above and below, optionally (iv) at least one cosmetic active ingredient, in particular as defined above and below; preferably, composition "C4" does not comprise (i) at least one polyester of formula (I), its optical or geometric isomers, or its organic acid or base salts or mineral, and / or solvated, such as hydrates, as defined above and below; and - possibly a composition, referred to as "C5", comprising iv) at least one cosmetic active ingredient, in particular as defined above and below; preferably, composition "C5" does not include i) at least one polyester of formula (I) its optical, geometric isomers, its organic or mineral acid or base salts, and / or solvates, such as hydrates, as defined above and below and does not include ii) at least one crosslinking agent, it being understood that compositions "Cl", "C4" and "C5" may include v) one or more fatty substances, in particular at least one oil, preferably volatile as defined above and below, more preferably isododecane.

[0085] According to one aspect of the invention, the process for treating keratinous materials, in particular for the care and / or makeup of the skin, lips, eyelashes and / or eyebrows and / or for the care, styling and / or coloring of keratinous fibers, preferably hair, employs i) at least one polyester of formula (I) as well as its optical, geometric isomers, its organic or mineral acid or base salts, and / or solvates, such as hydrates, as defined above and below, or a composition comprising it or them, said composition "Cl" optionally comprising iv) at least one cosmetic active ingredient, in particular as defined below, notably selected from a) coloring agents, such as pigments, direct colorants, and mixtures thereof, b) active ingredients for the care of keratinous materials, preferably skin, c) UV filters, and d) mixtures thereof, and in particular at least one coloring agent, more particularly at least one pigment,and / or optionally v) at least one fatty substance; preferably, composition "Cl" does not include ii) a crosslinking agent.

[0086] According to another aspect, the process for treating keratinous materials according to the invention, in particular for the care and / or makeup of the skin, lips, eyelashes and / or eyebrows and / or for the care, styling and / or coloring of keratinous fibers, preferably hair, employs a composition, referred to as "C2", comprising i) at least one polyester of formula (I) as well as its optical, geometric isomers, its organic or mineral acid or base salts, and / or solvates, such as hydrates, as defined above and below, ii) at least one crosslinking agent, in particular as defined below, and optionally iv) at least one cosmetic active ingredient, in particular as defined above, and / or optionally v) at least one fatty substance; preferably, the composition "C2" does not include iv) a cosmetic active ingredient.

[0087] According to another aspect, the process for treating keratinous materials according to the invention, in particular for the care and / or makeup of the skin, lips, for eyelashes and / or eyebrows and / or for the care, styling and / or coloring of keratin fibers, preferably hair, implements a composition, called "C3", comprising i) at least one polyester of formula (I) as well as its optical, geometric isomers, its organic or mineral acid or base salts, and / or solvated, such as hydrates, as defined above and below, ii) at least one crosslinking agent, in particular as defined below, iv) at least one cosmetic active, in particular as defined above, and possibly v) at least one fatty substance.

[0088] According to another aspect, the process for treating keratinous materials according to the invention, in particular for the care and / or makeup of skin, lips, eyelashes and / or eyebrows and / or for the care, styling and / or coloring of keratin fibers, employs a composition referred to as "Cl" or i) at least one polyester of formula (I) as well as its optical and geometric isomers, its organic or mineral acid or base salts, and / or solvates, such as hydrates, as defined above and below, and a composition referred to as "C4", said composition "Cl" comprising i) at least one polyester of formula (I) as well as its optical and geometric isomers, its organic or mineral acid or base salts, and / or solvates, such as hydrates, as defined above and below, and optionally iv) at least one cosmetic active ingredient, in particular as defined above and below, and / or optionally v) at least a fatty substance,in particular as defined above and below, and said composition “C4” comprising ii) at least one crosslinking agent, in particular as defined above and below, and possibly iv) at least one cosmetic active ingredient, in particular as defined above and below, and / or possibly v) at least one fatty substance, in particular as defined above and below.

[0089] According to another variant of the process of the invention, the ingredient(s) i), optionally iv) and optionally v) are applied together, namely simultaneously, to the keratin materials in a first step, and then in a subsequent step, the ingredient(s) ii), optionally iv), and optionally v) are applied to said materials.

[0090] According to a particular embodiment, the process according to the invention comprises two successive application steps on said keratinous materials, of two different compositions.

[0091] According to a particular embodiment of the process, in the first step i) at least one polyester of formula (I) as well as its optical, geometric isomers, its organic or mineral acid or base salts, and / or solvates, such as hydrates, as defined above and below or a "Cl" composition containing it or them is applied to the keratin materials, then a "C4" composition is applied to said keratin materials.

[0092] According to yet another embodiment of the process of the invention, ingredient(s) ii) and optionally iv) and / or v) is / are applied to the keratin materials, then ingredient(s) i), and optionally iv) at least one cosmetic active ingredient and / or v) at least one fatty substance, in particular as defined above, are applied to said keratin materials. In particular, composition “C4” is applied to the keratin materials, then i) at least one polyester of formula (I) as well as its optical, geometric, and / or solvated acid or base salts, such as hydrates, as defined above and below, or a composition “Cl” containing it or them, is applied.

[0093] According to another variant of the method according to the invention, i) or a composition "Cl" containing i), said composition "Cl" comprising v) optionally at least one oil, in particular volatile as defined above and below, preferably isododecane, is applied, and sequentially a composition "C4" containing ii), optionally iv), and optionally v), preferably i) or the composition "Cl" containing i) being applied before the composition "C4".

[0094] According to a particular embodiment of the process, in the first step a composition “C2” is applied to the keratinous materials, then a composition “C4” is applied to said keratinous materials.

[0095] According to another embodiment of the process according to the invention, a composition “C2” containing i) at least one polyester of formula (I) as well as its optical, geometric isomers, its organic or mineral acid or base salts, and / or solvates, such as hydrates, and ii) at least one crosslinking agent, optionally iv) at least one cosmetic active ingredient, and optionally v) at least one oil, in particular a volatile oil as defined above and below, preferably isododecane, is applied, and sequentially a composition “C4” containing ii) at least one crosslinking agent, optionally at least one cosmetic active ingredient, iv), and optionally v) at least one oil, in particular a volatile oil as defined above and below, preferably composition “C2” being applied before composition “C4”,and given that the possible crosslinking agent(s) contained in composition "C2" may be identical or different from the crosslinking agent(s) contained in composition "C4", preferably the crosslinking agent(s) are different.

[0096] The compositions “Cl”, “C2”, “C3”, “C4” and / or “C5” of the process according to the invention which comprise v) at least one fat, in particular at least one oil, and water, may be in the form of a direct or reverse emulsion.

[0097] The compositions “Cl”, “C2”, “C3”, “C4” and / or “C5” of the process according to the invention can therefore be applied directly as such to the target keratinous materials or even be formed directly on the surface of these keratinous materials.

[0098] According to the invention, three modes of implementation are distinguished, called "1-step application mode", "2-step application mode" and "3-step application mode".

[0099] According to one embodiment of the process of the invention, the process is carried out in one step by applying to the keratinous materials the composition “Cl”, “C2” or “C3”, as defined above.

[0100] Thus, according to one embodiment, the treatment process according to the invention comprises a single step of applying i) at least one polyester of formula (I) as well as its optical, geometric isomers, its organic or mineral acid or base salts, and / or solvated, such as hydrates, as defined above and below, or of composition "Cl", or of composition "C2", or of composition "C3" on said keratin materials; preferably the treatment process according to the invention comprises either a single step of applying composition "C2" or composition "C3" on said keratin materials; or two successive steps of applying to said keratin materials, two different compositions, preferably composition "Cl" then composition "C4";that is, three successive application steps on the said keratinous materials, of three different compositions, preferably composition "Cl", then composition "C4", then composition "C5".

[0101] The term “one-step application method” means the direct application to the target keratinous materials of a single composition according to the invention, namely composition “Cl” or “C2” or “C3”.

[0102] The term "1-step application method" also means the single application of i) at least one polyester of formula (I) and its optical, geometric isomers, its organic or mineral acid or base salts, and / or solvates, such as hydrates, as defined above and below.

[0103] After application of composition "Cl", or of i) at least one polyester of formula (I) as well as its optical, geometric isomers, its organic or mineral acid or base salts, and / or solvates, such as hydrates, as defined above and below, or of composition "C2", or of composition "C3", a persistent and non-sticky deposit is advantageously obtained. The deposit obtained is also glossy and resistant to edible oils, water, sebum, and rubbing.

[0104] According to another embodiment of the process of the invention, the process is carried out in two steps.

[0105] The term "2-step application method" refers to the successive application, to the target keratinous material, of two different compositions, for example "Cl" and "C4", or "C2" and "C4", or "C3" and "C4". Preferably, "Cl" then "C4", "C2" then "C4", or "C3" then "C4".

[0106] The term "2-step application method" also means the sequential application on the target keratin material of i) at least one polyester of formula (I) as well as its optical, geometric isomers, its organic or mineral acid or base salts, and / or solvates, such as hydrates, as defined above and below, and of a "C4" composition.

[0107] According to another embodiment, the process of the invention is carried out in 3 steps.

[0108] The term "3-gesture application mode" refers to the sequential application of 3 distinct compositions “Cl” to “C5”. According to this method of application, for example, according to one embodiment, the following successive application is carried out on keratinous materials: a) a composition “Cl”, then |3) a composition “C4”, then y) a composition “C5”, preferably “Cl” then “C4” respectively “C5” or “C5” respectively “C4”.

[0109] According to another embodiment, the sequential application is carried out on the keratinous materials, a) of a composition for example "C4", and |3) of a composition "Cl" or "C2", and again y) of a composition "C5", preferably the composition "C4" is applied before the composition "Cl" or "C2".

[0110] The application method 3 steps also means the sequential application of i) at least one polyester of formula (I) as well as its optical, geometric isomers, its organic or mineral acid or base salts, and / or solvates, such as hydrates, as defined above and below, of a composition “C4” and a composition “C5”.

[0111] In 2- or 3-step application modes, the composition is applied first for example “Cl” or i), or “C2” is conventionally referred to as “base coat”, and the composition(s) which are superimposed on it are generally referred to as “top coat”.

[0112] After applying the different compositions "Cl" or i), and "C2" to "C5", a permanent and non-sticky deposit is advantageously obtained. The deposit obtained is also glossy and resistant to edible oils, water, and shampoos.

[0113] According to a particular embodiment, the compositions are applied to dry keratinous materials.

[0114] According to a particular embodiment, the compositions are applied to wet or moist keratinous materials, i.e. to keratinous materials containing water on the surface.

[0115] According to a particular embodiment, the keratin materials are dried after application of compositions "C1" or "C2" (i) and "C2" to "C5", in particular after application of each different composition. The drying step can be carried out with a drying device such as a helmet, a hairdryer, or a climazon, more preferably a hairdryer. When the drying step is When using a helmet or hair dryer, the drying temperature is greater than or equal to 40°C and strictly less than 120°C.

[0116] During the drying of keratin fibers, mechanical action can be applied to the strands, such as combing, brushing, or running the fingers through them. This operation can also be carried out once the hair has dried, whether naturally or otherwise.

[0117] After the drying step of the keratin fibers, a shaping step of the keratin fibers can be carried out using a flat iron, a crimping or curling iron, a steam iron, or a heated comb, preferably a flat iron, a crimping or curling iron, or a steam iron, more preferably a steam iron. Preferably, the shaping step is carried out at a temperature ranging from 150 °C to 230 °C, more preferably from 160 °C to 210 °C, and even more preferably from 180 °C to 210 °C. Iron can be applied to keratin fibers by successive separate touches ranging from 100 milliseconds to 2 minutes, more preferably from 500 milliseconds to 1 minute, more preferably still from 1 second to 30 seconds, even better from 3 seconds to 20 seconds, or even from 4 seconds to 10 seconds, or by progressive movement or gliding along the hair.Ideally, the iron should be applied in a continuous movement from the root to the tip of the hair, in one or more passes.

[0118] According to one aspect, the present invention relates to a process for treating, in particular cosmetic, keratinous materials, in particular for the care and / or makeup of the skin, lips, eyelashes and / or eyebrows and / or for the care, styling and / or coloring of keratinous fibers, preferably hair, comprising a step of applying to the keratinous fibers, i) at least one polyester of formula (I) as well as its optical, geometric isomers, its salts of organic or mineral acid or base, and / or solvated, such as hydrates, as defined above and below, or of a composition "Cl" containing it or them, or of a composition "C2" or of a composition "C3", in particular containing at least one coloring material, in particular as defined above, and more particularly at least one pigment.

[0119] According to one aspect, the present invention relates to a method, in particular cosmetic, for the treatment of keratinous materials, in particular skin and / or lips and / or eyelashes and / or eyebrows, in particular for the care and / or makeup of keratinous materials, in particular skin, lips, eyelashes and / or eyebrows, comprising a step of applying to said keratinous materials, in particular to said skin or said lips or said eyelashes or said eyebrows, a composition "C3", in particular containing at least one coloring material, in particular as defined above, and more particularly at least one pigment.

[0120] According to another aspect, the present invention relates to a cosmetic treatment method for the care and / or makeup of keratinous materials, in particular of the skin, lips, eyelashes and / or eyebrows, comprising the successive application of at least:

[0121] - i) at least one polyester of formula (I) comprising at least two functions acetoacetates as defined above and below or of a composition called "Cl" comprising the and possibly comprising iv) at least one cosmetic active ingredient, in particular as defined above and below, and / or possibly v) at least one fatty substance, in particular as defined above and below; then - a composition, called "C4", comprising ii) at least one crosslinking agent, in particular as defined below, and possibly iv) at least one cosmetic active ingredient, in particular as defined above and below, and / or possibly v) at least one fatty substance, in particular as defined above and below; at least one of the compositions "Cl" and / or "C4" containing at least one colouring material, in particular as defined above and below, preferably at least one pigment, and more preferably composition "Cl" includes at least one pigment.

[0122] According to another aspect, the present invention relates to a cosmetic treatment method for keratinous materials, in particular the care and / or makeup of keratinous materials, in particular of the skin, lips, eyelashes and / or eyebrows, comprising the sequential application of at least: - i) at least one polyester of formula (I) comprising at least two acetoacetate functions as defined above and below, or a "Cl" composition as defined above; and - a "C4" composition as defined above; and - a "C5" composition as defined above; and it being understood that the "C1" and / or "C4" and / or "C5" compositions contain at least one coloring matter, in particular as defined below, preferably at least one pigment. Preferably, the "C5" composition comprises at least one pigment.

[0123] According to another aspect, the present invention relates to a cosmetic treatment method for keratin fibers, in particular for the care, styling and / or coloring of keratin fibers, preferably hair, comprising the successive application to said keratin fibers of at least: - i) at least one polyester of formula (I) comprising at least two acetoacetate functions as defined above and below, or a composition, referred to as "Cl", containing them and possibly comprising iv) at least one cosmetic active ingredient, in particular as defined above and below, and / or possibly v) at least a fatty substance, in particular as defined above and below; preferably, composition "Cl" does not include ii) a crosslinking agent; then - a composition, referred to as "C4", comprising ii) at least one crosslinking agent, in particular as defined above and below, possibly iv) at least one cosmetic active ingredient, in particular as defined above and below, and / or possibly v) at least one fatty substance, in particular as defined above and below; preferably, the "C4" composition does not comprise i) at least one polyester of formula (I) its optical, geometric isomers, its organic or mineral acid or base salts, and / or solvates, such as hydrates, as defined above and below; at least one of the compositions "Cl" and / or "C4" containing at least one colouring material, in particular as defined above and below, preferably at least one pigment, and more preferably composition "Cl" includes at least one pigment.

[0124] According to another aspect, the present invention relates to a cosmetic treatment method for keratin fibers, in particular for the care, styling and / or coloring of keratin fibers, preferably hair, comprising the successive application of at least: - i) at least one polyester of formula (I) comprising at least two acetoacetate functions as defined above and below, or a "Cl" or "C2" or "C3" composition as defined above; and / or - a "C4" composition as defined previously; provided that the process employs together or separately i) at least one polyester of formula (I) comprising at least two acetoacetate functions as defined above and below, and that the compositions "Cl", "C2", "C3" and / or "C4" may be anhydrous, aqueous such as hydroalcoholic and / or comprise one or more fatty substances v), in particular as described below.

[0125] According to another aspect, the present invention relates to a cosmetic treatment method for keratin fibers, in particular for the care, styling and / or coloring of keratin fibers, preferably hair, comprising the sequential application of at least: - i) at least one polyester of formula (I) comprising at least two acetoacetate functions as defined above and below, or a "Cl" composition as defined above; then - a "C4" composition as defined previously; then - a "C5" composition as defined previously; it being understood that the compositions "Cl" and / or "C4" and / or "C5" contain at least one coloring matter, in particular as defined below, preferably at least one pigment. Preferably, the "C5" composition includes at least one pigment.

[0126] According to another aspect, the present invention relates to a cosmetic treatment method for keratin fibers, in particular for the care, styling and / or coloring of keratin fibers, preferably hair, comprising the successive application of at least: - a "C2" or "C3" composition as defined above; and - a "C4" composition as defined previously; provided that compositions “C2” or “C3” contain at least iv) a colouring material, in particular as defined below, and / or composition “C4” contains at least one colouring material, in particular as defined below, preferably composition “C2” or “C3” includes at least one pigment.

[0127] According to another aspect, the present invention relates to a cosmetic treatment method for coloring keratin fibers, particularly hair, and / or applying makeup to keratin materials, particularly skin, comprising applying at least: - a composition, called "C2" as defined previously or a composition, called "C3" as defined previously; it being understood that compositions “C2” or “C3” may include v) one or more fats.

[0128] According to another aspect, the present invention relates to a cosmetic treatment process for keratin fibers, for styling keratin fibers, preferably hair, comprising applying to said keratin fibers at least: - i) at least one polyester of formula (I) comprising at least two acetoacetate functions as defined above and below, or a "Cl" composition as defined above; preferably, the "Cl" composition does not comprise ii) a crosslinking agent; or - a composition, called "C2" as defined previously;

[0129] - a composition, referred to as "C3" as defined above; it being understood that the compositions “Cl” or “C2” or “C3” may include (v) one or more fats.

[0130] COMPOUNDS OF FORMULA (I)

[0131] As indicated above, the treatment process according to the invention comprises the application on keratin materials of at least one polyester of formula (I) comprising at least two acetoacetate functions comprising at least two acetoacetate functions, as well as its optical, geometric and / or solvated isomers, such as hydrates, or a composition containing it or them.

[0132] Thus, the treatment process according to the invention comprises applying to keratinous materials at least one polyester of formula (I) comprising at least two acetoacetate functions, as well as its optical, geometric and / or solvated isomers, such as hydrates, or a composition containing it or them: (Z)-[OC(O)-C(Ra)(Rb)-C(O)-R4]u(I) formula (I) in which: - Z designates a multivalent radical derived from: an alkyd resin (A) obtained by reaction: - of 10% to 62% mass of at least one polyol; - from 10% to 62% mass of at least one polyacid; - 35% to 60% by mass of at least one fatty alcohol and / or at least one mono-fatty acid; and - from 0% to 20% mass of at least one monocarboxylic acid; the mass percentages being expressed in relation to the total weight of the alkyd resin (A); Or of an alkyd resin (B) resulting from the reaction of an alkyd resin (A) containing ethylenic unsaturations with at least one (poly)hydroxy thiol; - u is an integer greater than 2; - R4 represents a monovalent hydrocarbon radical in C1 to C6, linear or branched, saturated or unsaturated, preferably a (Ci-C4)alkyl group, in particular methyl or tert-butyl, more preferably methyl; - Ra and Rb, identical or different, represent a hydrogen atom or a (Ci-C4)alkyl group, preferably a hydrogen atom; and ii) possibly at least one crosslinking agent.

[0133] Preferably, the polyesters of formula (I) are such that all the radicals -OC(O)-0^)^)-0(0)-1^ are identical.

[0134] Preferably, the molecular weight of the alkyd resin (A) or (B) used in the preparation of the polyesters of formula (I) is between 500 and 80,000 g / mol.

[0135] Preferably, the molecular weight of the polyesters of formula (I) according to the invention is between 600 and 100,000 g / mol.

[0136] Preferably, the mass ratio between the alkyd resin (A) or (B) used in the preparation of the polyesters of formula (I) and the polyester(s) of formula (I) is between 65 and 95.

[0137] Preferably, the mass ratio between u motifs -OC(O)-C(Ra)(Rb)-C(O)-R4 and the polyester(s) of formula (I) is between 5 and 35 in the polyester(s) of formula (I) according to the invention.

[0138] Preferably, the mass ratio between the alkyd resin (A) or (B) used in the preparation of the polyesters of formula (I) and u motifs -OC(O)-C(Ra)(Rb)-C(O)-R4 varies between 65 / 35 and 95 / 5 in the polyester(s) of formula (I) according to the invention.

[0139] According to a particular embodiment of the invention, (Z) represents a multivalent radical comprising from 40 to 6000 carbon atoms, terminated by m -O- radicals and n -C(O)ORz radicals, with: - m an integer greater than 2, preferably greater than or equal to 10, - n an integer greater than or equal to zero, - Rz a hydrogen atom or an alkyl group comprising from 4 to 40 atoms, in particular from 5 to 32 atoms, and more preferably from 6 to 24 carbon atoms, said multivalent radical being cyclic or acyclic, branched, saturated or unsaturated, interrupted by several ester radicals -OC(O)- or -C(O)-O-, and possibly interrupted by one or more non-adjacent sulfur atoms S.

[0140] More particularly, the radical(s) -C(O)ORz is / are selected from the following: t-butyl esters, oleyl esters, caprylic acid esters, 2-ethylhexanoic acid esters, 4,5-dimethylhexanoic acid esters, 2-heptylheptanoic acid esters, 3,5,5-trimethylhexanoic acid esters, octanoic acid esters, isooctanoic acid esters, nonanoic acid esters, decanoic acid esters, isononanoic acid esters, lauric acid esters, tridecanoic acid esters, myristic acid esters, palmitic acid esters, stearic acid esters, isostearic acid esters, arachidic acid esters, behenic acid esters, cerotic (hexacosanoic) acid esters, 3-cyclopentylpropionic acid esters, 3-cyclohexylpropionic acid, cyclohexylacetic acid, 4-cyclohexylbutyric acid, caproleic acid, undecylenic acid, dodecylenic acid, myristoleic acid, palmitoleic acid, oleic acid, linoleic acid, linolenic acid, elaidic acid, gondoic acid, erucic acid. Alkyd resins (A).

[0141] The alkyd resin(s) (A) used in the preparation of the polyesters of formula (I) are obtained by reaction: - from 10% to 62% mass of at least one polyol; - from 10% to 62% mass of at least one polyacid; - 35% to 60% by mass of at least one fatty alcohol and / or at least one monoacid bold; and - from 0% to 20% by mass of at least one monocarboxylic acid; mass percentages being expressed in relation to the total weight of the alkyd resin (A).

[0142] Thus, the alkyd resin(s) (A) used in the preparation of the polyesters of formula (I) can be obtained as a result of a one-step polycondensation reaction.

[0143] Preferably, the hydroxyl value of the alkyd resin(s) obtained is between 50 and 300 mg KOH / g.

[0144] Preferably, the acid value of the alkyd resin(s) obtained is between 0 and 15 mg KOH / g.

[0145] Preferably, the polycondensation synthesis of the alkyd resin(s) (A) is carried out without solvent.

[0146] Preferably, polycondensation is carried out under an inert atmosphere such as an argon atmosphere.

[0147] Preferably, polycondensation is carried out at a temperature between 160 °C and 270 °C, and more preferably between 170 °C and 260 °C for a duration of 1h to 24h.

[0148] According to a first embodiment of the invention, the alkyd resin(s) (A) are obtained by one-step polycondensation of: - 0% to 12% mass of at least one diol; - 20% to 50% by mass of at least one compound containing at least 3 alcohol functions; - 10% to 30% mass of at least one dicarboxylic acid compound; - 0% to 17% mass of at least one compound containing at least 3 carboxylic acid functions; - 0% to 10% by mass of at least one monocarboxylic acid compound; and - 35% to 60% by mass of at least one mono-fatty acid; mass percentages being expressed in relation to the total weight of the alkyd resin (A).

[0149] According to this variant, the hydroxyl value of the alkyd resin(s) obtained is between 50 and 300 mg KOH / g.

[0150] According to a second embodiment of the invention, the alkyd resin(s) (A) are obtained by one-step polycondensation of: - 10% to 30% by mass of at least one diol; and - 0% to 12% by mass of at least one compound containing at least 3 alcohol functional groups; and - 0% to 12% by mass of at least one dicarboxylic acid compound; and - 20% to 50% by mass of at least one compound containing at least 3 carboxylic acid functions; and - 0% to 20% by mass of at least one monocarboxylic acid compound; and - 35% to 60% by mass of at least one fatty alcohol; mass percentages being expressed in relation to the total weight of the alkyd resin (A), it being understood that at least one of the dicarboxylic acid compounds and compounds comprising at least 3 carboxylic acid functions, and / or at least one of the fatty alcohols, contains at least one ethylenic unsaturation.

[0151] Preferably, the hydroxyl value of the alkyd resin(s) obtained is between 50 and 800 mg KOH / g.

[0152] Preferably, the dicarboxylic acid(s) comprising at least one ethylenic unsaturation are chosen from maleic acid, fumaric acid, muconic acid, itaconic acid.

[0153] Preferably, the compound(s) comprising at least 3 carboxylic acid functions and comprising at least one ethylenic unsaturation are chosen from tricarboxylic acids such as cyclohexanetricarboxylic acid, trimellitic acid, 1,2,3-benzenetricarboxylic acid, 1,3,5-benzenetricarboxylic acid; citric acid, tetracarboxylic acids such as butanetetracarboxylic acid, pyromellitic acid and mixtures thereof; preferably from tricarboxylic acids; more preferably from citric acid.

[0154] Preferably, the fatty alcohol(s) comprising at least one ethylenic unsaturation are chosen from 9-decen-l-ol, citronellol, oleic alcohol, linoleic alcohol and mixtures thereof, more preferably oleic alcohol.

[0155] According to one embodiment of this variant, the alkyd resin(s) (A) are obtained by one-step polycondensation of: - 10% to 30% mass of at least one diol; - 0% to 12% mass of at least one compound containing at least 3 alcohol functions; - 0% to 12% mass of at least one dicarboxylic acid compound; - 20% to 50% by mass of at least one compound containing at least 3 carboxylic acid functions; - 0% to 20% by mass of at least one monocarboxylic acid compound; and - 35% to 60% by mass of at least one fatty alcohol, preferably saturated; the mass percentages being expressed in relation to the total weight of the alkyd resin (A), it being understood that at least one of the dicarboxylic acid compounds and compounds comprising at least 3 carboxylic acid functions, preferably at least one of the dicarboxylic acid compounds, contains at least one ethylenic unsaturation.

[0156] According to another embodiment of this variant, the alkyd resin(s) (A) are obtained by one-step polycondensation of: - 10% to 30% mass of at least one diol; - 0% to 12% mass of at least one compound containing at least 3 alcohol functions; - 0% to 12% mass of at least one dicarboxylic acid compound; - 20% to 50% by mass of at least one compound containing at least 3 carboxylic acid functions; - 0% to 20% by mass of at least one monocarboxylic acid compound; and - 35% to 60% by mass of at least one fatty alcohol; the mass percentages being expressed in relation to the total weight of the alkyd resin (A), it being understood that at least one of the dicarboxylic acid compounds and compounds comprising at least 3 carboxylic acid functions, preferably at least one of the dicarboxylic acid compounds, and that at least one of the fatty alcohols contains at least one ethylenic unsaturation.

[0157] According to a preferred embodiment of this variant, the alkyd resin(s) (A) are obtained by one-step polycondensation of: - 10% to 30% mass of at least one diol; - 0% to 12% mass of at least one compound containing at least 3 alcohol functions; - 0% to 12% by mass of at least one dicarboxylic acid compound, preferably saturated; - 20% to 50% by mass of at least one compound comprising at least 3 carboxylic acid functions, preferably saturated; - 0% to 20% by mass of at least one monocarboxylic acid compound; and - 35% to 60% by mass of at least one fatty alcohol; the mass percentages being expressed in relation to the total weight of the alkyd resin (A), it being understood that at least one of the fatty alcohols contains at least one ethylenic unsaturation.

[0158] Preferably, the alkyd resin(s) (A) used in the preparation of the polyesters of formula (I) according to the invention are formed by polycondensation of: a) at least one fatty alcohol and / or at least one mono-fatty acid, b) at least one polyol, c) at least one dicarboxylic acid compound and / or compound comprising at least 3 carboxylic acid functions, d) optionally at least one mono-carboxylic acid compound.

[0159] Fatty alcohols

[0160] According to one embodiment, the alkyd resin(s) (A) are obtained by a polycondensation step using at least one fatty alcohol.

[0161] By "fatty alcohol" is meant a monoalcohol, saturated or unsaturated, linear or branched, or cyclic, comprising from 8 to 32 carbon atoms, in particular from 10 to 28 atoms of carbon, ideally 14 to 20 carbon atoms. It is of course possible to use a mixture of such alcohols, provided that at least one fatty alcohol contains at least one ethylenic unsaturation.

[0162] Preferably, the fatty alcohol(s) are chosen from saturated or unsaturated, linear or branched monoalcohols comprising 8 to 32 carbon atoms, in particular 10 to 28 carbon atoms, better 14 to 20 carbon atoms, it being understood that at least one fatty alcohol contains at least one ethylenic unsaturation.

[0163] In particular, the fatty alcohol(s) may be chosen from among saturated fatty monoalcohols, more preferably from octan-l-ol, nonan-l-ol, decan-l-ol, dodecan-l-ol, tetradecan-l-ol, hexadecan-l-ol, octadecanol, docosanol, triacontanol, octan-2-ol, 2-butyloctanol, hexyldecanol, 2-octyldecanol and / or unsaturated monoalcohols, in particular 9-decen-l-ol, citronellol, oleic alcohol, linoleic alcohol and mixtures thereof.

[0164] Advantageously, the alkyd resin(s) (A) are obtained by a polycondensation step using one or more fatty alcohols comprising from 10 to 28 carbon atoms, preferably comprising from 14 to 20 carbon atoms.

[0165] More advantageously, the alkyd resin(s) (A) are obtained by a polycondensation step using one or more unsaturated fatty alcohols, preferably monounsaturated. Even more advantageously, the alkyd resin(s) (A) are obtained by a polycondensation step using one or more unsaturated fatty alcohols, one of which is oleic alcohol.

[0166] Preferably, the alkyd resin(s) (A) are obtained by a polycondensation step using a single fatty alcohol containing at least one ethylenic unsaturation, preferably a single ethylenic unsaturation. Preferably, the fatty alcohol used is oleic alcohol.

[0167] According to another embodiment, the alkyd resin(s) (A) are obtained by polycondensation: - of at least one diol; - of at least one compound containing at least 3 carboxylic acid functions; and - of at least one fatty alcohol; it being understood that at least one fatty alcohol contains at least one ethylenic unsaturation, said polycondensation possibly involving at least one compound comprising at least 3 alcohol functions, possibly at least one dicarboxylic acid compound, and possibly at least one monocarboxylic acid compound.

[0168] According to a preferred embodiment, the alkyd resin(s) (A) are obtained by polycondensation: - of at least one fatty alcohol, at least one of which contains at least one ethylenic unsaturation; and - of at least one compound containing at least 3 carboxylic acid functions; and - of at least one diol; more preferably: by polycondensation of oleic alcohol, at least one compound comprising at least 3 carboxylic acid functions, and at least one diol; even more preferably by polycondensation: - 35% to 60% by mass, such as 50% by mass, of oleic alcohol; - 20% to 50% by mass, preferably 20% to 30% by mass, more preferably 25% to 30% by mass, of at least one compound comprising at least 3 carboxylic acid functions, such as citric acid; and - 10% to 30% by mass, preferably 20% to 30% by mass, more preferably 20% to 25% by mass, of at least one diol, such as 1-10-decanediol; mass percentages being expressed in relation to the total weight of the alkyd resin (A).

[0169] According to another embodiment, the alkyd resin(s) (A) are obtained without the use of fatty alcohol.

[0170] Polyols

[0171] The alkyd resin(s) (A) are obtained by one-step polycondensation of 10% to 62% mass of at least one polyol, the mass percentages being expressed in relation to the total weight of the alkyd resin (A).

[0172] By "polyol" is meant an organic compound comprising 2 to 8 hydroxyl groups, preferably 3 to 6 hydroxyl groups.

[0173] The polyols used for the preparation of the alkyd resin(s) (A) are advantageously saturated or unsaturated, linear, branched or cyclic compounds comprising from 2 to 50 carbon atoms, in particular from 6 to 40 carbon atoms, and more preferably from 8 to 37 carbon atoms, optionally comprising one or more non-adjacent oxygen atoms intercalated between two carbon atoms, and comprising from 2 to 8 hydroxyl groups.

[0174] Preferably, a polyol used for the preparation of the alkyd resin(s) (A) does not include acid functions, amine functions, or thiol functions.

[0175] Among polyols, a distinction is made between: diols, which comprise 2 hydroxyl groups, and compounds comprising at least 3 alcohol functions, in particular 3 to 6 alcohol functions.

[0176] According to one embodiment, the alkyd resin(s) (A) are obtained by one-step polycondensation using 10% to 62% by mass of at least one polyol, said at least one polyol containing 0% to 30% by mass of at least one diol, mass percentages being expressed in relation to the total weight of the alkyd resin (A).

[0177] According to a preferred embodiment, the diol(s) are saturated.

[0178] A diol used for the preparation of the alkyd resin(s) (A) is preferably chosen from: isosorbide, hexamethylene glycol, hexylene glycol, hexanediol, neopentyl glycol, 1,2-propanediol, 1,3-propanediol, 1,2 butanediol, 1,3-butane diol, 2,3-butanediol, 1,4-butanediol, 2,4-butanediol, 3,4-butanediol, 1,4-pentanediol, 1,5-pentanediol, 2,2,4-trimethyl-1,3-pentanediol, 1,6-hexanediol, 1,2-octanediol, 1,8-octanediol, 1,10-decanediol, 2,2-dimethyl-1,3-propanediol, 3-methyl- 1,5-pentanediol, isoprene glycol, 1,12-octadecanediol, 1,10-decanediol, 1,16-hexadecanediol, 1,12-dodecanediol, Pripol 2033 (18,18'-oxybis[(9Z,12Z)-9,12-octadecadiene-l-ol]), or oligomers containing 2 alcohol functions such as polypropanediol with Mw ranging from 100 to 1000, and mixtures thereof.

[0179] Preferably, the diol(s) are chosen from 1,10-decanediol, Pripol 2033 and mixtures thereof.

[0180] According to another embodiment, the alkyd resin(s) (A) are obtained following the implementation of 1% to 30% mass, preferably 4% to 25% mass, of at least one diol relative to the total weight of the alkyd resin (A), preferably chosen from Pripol 2033, 1,10-decanediol, and mixtures thereof.

[0181] According to one embodiment, the alkyd resin(s) (A) are obtained by polycondensation of: - 0% to 12% by mass, preferably 0% to 10% by mass, of at least one diol, preferably a single diol; - 20% to 50% by mass of at least one compound containing at least 3 alcohol functions; - 10% to 30% mass of at least one dicarboxylic acid compound; - 0% to 17% mass of at least one compound containing at least 3 carboxylic acid functions; - 0% to 10% mass of at least one monocarboxylic acid compound; and - 35% to 60% mass of at least one monofatty acid, the mass percentages being expressed in relation to the total weight of the alkyd resin (A).

[0182] According to yet another embodiment, the alkyd resin(s) (A) are obtained by polycondensation of: - 10% to 30% by mass, preferably 15% to 28% by mass, more preferably 18% to 26% by mass of at least one diol, preferably of a single diol; - 0% to 12% mass of at least one compound containing at least 3 alcohol functions; - 0% to 12% mass of at least one dicarboxylic acid compound; - 20% to 50% by mass of at least one compound containing at least 3 carboxylic acid functions; - 0% to 20% by mass of at least one monocarboxylic acid compound; and - 35% to 60% mass of at least one fatty alcohol, of which at least one contains at least one ethylenic unsaturation; mass percentages being expressed in relation to the total weight of the alkyd resin (A).

[0183] According to one embodiment, the alkyd resin(s) (A) are obtained without the use of diol.

[0184] According to one embodiment, the alkyd resin(s) (A) are obtained by a polycondensation step using 10% to 62% by mass of at least one polyol, said at least one polyol containing 0% to 50% by mass of at least one compound comprising at least 3 alcohol functions, the mass percentages being expressed in relation to the total weight of the alkyd resin (A).

[0185] The compound(s) comprising at least 3 alcohol functions, in particular 3 to The six alcohol functional groups may be carbon compounds, particularly hydrocarbons, linear, branched, or cyclic, saturated or unsaturated, comprising from 3 to 36 carbon atoms, in particular from 3 to 24, or even from 4 to 18 carbon atoms, or even from 5 to 10 carbon atoms, and from 3 to 8 hydroxyl (OH) groups, more preferably from 3 to 6 hydroxyl groups, and may further comprise one or more non-adjacent oxygen atoms intercalated between two carbon atoms (ether functional group).

[0186] According to a preferred embodiment, the compound(s) comprising at least three alcohol functional groups are saturated.

[0187] The compound(s) comprising at least 3 alcohol functions, in particular 3 to 6 alcohol functions, used for the preparation of the alkyd resin(s) (A) are selected from: - triols, such as glycerol, trimethylolpropane; - tetraols, such as pentaerythritol (tetramethylolmethane), erythritol, diglycerol; - pentols such as xylitol, triglycerol; - hexols such as sorbitol, mannitol or dipentaerythritol; and their mixtures.

[0188] Preferably, the compound(s) comprising at least 3 alcohol functions, in particular 3 to 6 alcohol functions, are chosen from tetraols, pentols, hexols and mixtures thereof.

[0189] More preferably, the compound or compounds comprising at least 3 alcohol functions, in particular 2 to 6 alcohol functions, are chosen from pentaerythritol, xylitol, dipentaerythritol and mixtures thereof.

[0190] According to one embodiment, the alkyd resin (A) is obtained following the implementation of 1% to 50% by mass, preferably 4% to 50% by mass, more preferably 15% to 40% by mass of at least one compound comprising at least 3 alcohol functions, preferably chosen from pentaerythritol, xylitol, dipentaerythritol and mixtures thereof, the mass percentages being expressed in relation to the total weight of the alkyd resin (A).

[0191] According to one embodiment, the alkyd resin(s) (A) are obtained by polycondensation of: - 0% to 12% by mass, preferably 0% to 10% by mass, of at least one diol, preferably a single diol; - 20% to 40% by mass of at least one compound comprising at least 3 alcohol functions, preferably chosen from pentaerythritol, xylitol, dipentaerythritol and mixtures thereof; - 10% to 30% mass of at least one dicarboxylic acid compound; - 0% to 17% mass of at least one compound containing at least 3 carboxylic acid functions; - 0% to 10% mass of at least one monocarboxylic acid compound; and - 35% to 60% mass of at least one monofatty acid, the mass percentages being expressed in relation to the total weight of the alkyd resin (A).

[0192] According to yet another embodiment, the alkyd resin(s) (A) are obtained by polycondensation of: - 10% to 30% by mass, preferably 15% to 28% by mass, more preferably 18% to 26% by mass of at least one diol, preferably of a single diol; - 0% to 12% by mass, preferably 0% by mass, of at least one compound comprising at least 3 alcohol functions; - 0% to 12% mass of at least one dicarboxylic acid compound; - 20% to 50% by mass of at least one compound containing at least 3 carboxylic acid functions; - 0% to 20% by mass of at least one monocarboxylic acid compound; and - 35% to 60% by mass of at least one fatty alcohol, of which at least one contains at least one ethylenic unsaturation; mass percentages being expressed in relation to the total weight of the alkyd resin (A).

[0193] According to one embodiment, the alkyd resin (A) is obtained without the use of a compound comprising at least 3 alcohol functions.

[0194] Monocarboxylic acids

[0195] The alkyd resin(s) (A) are obtained by a polycondensation step using 0% to 20% mass of at least one monocarboxylic acid compound, the mass percentages being expressed in relation to the total weight of the alkyd resin (A).

[0196] By “monoacid” is meant an aromatic or non-aromatic monocarboxylic acid or its cyclic lactone form.

[0197] By "aromatic monoacid" is meant a monocarboxylic acid carried by an aromatic (poly)cycle, said (poly)cycle being optionally substituted by one or more Ci-C7 alkyl and / or Ci-C7 alkoxy radicals.

[0198] Among the aromatic monocarboxylic acids that can be used in the context of the invention, benzoic acid, o-toluic acid, m-toluic acid, p-toluic acid, 1-naphthoic acid, 2-naphthoic acid, 4-tert-butylbenzoic acid, l-methyl-2-naphthoic acid, 2-isopropyl-1-naphthoic acid, and mixtures thereof may be mentioned.

[0199] By "non-aromatic monocarboxylic acid" is meant a monocarboxylic acid, saturated or unsaturated, linear, branched or cyclic, optionally in its esterified or lactonized form, comprising from 1 to 7 carbon atoms, in particular from 2 to 7 carbon atoms and even better from 3 to 7 carbon atoms. It is of course possible to use a mixture of such acids.

[0200] Preferably, by non-aromatic monocarboxylic acid, we mean a monocarboxylic acid, saturated, linear or branched, possibly in its lactonized form comprising 5 to 7 carbon atoms.

[0201] Among the non-aromatic monocarboxylic acids that can be used in the context of the invention, the following may be mentioned preferentially: hexanoic acid, epsilon-caprolactone.

[0202] According to one embodiment, the alkyd resin (A) is obtained following the implementation of at least one monocarboxylic acid or at least one lactone, preferably chosen from benzoic acid, hexanoic acid, epsilon-caprolactone and mixtures thereof.

[0203] Preferably, the mass concentration of monocarboxylic acid or lactone is less than or equal to 10% by mass, the mass percentages being expressed in relation to the total weight of the alkyd resin (A).

[0204] According to a preferred embodiment, the polycondensation leading to the alkyd resin (A) does not involve monocarboxylic acid.

[0205] According to one embodiment, the alkyd resin(s) (A) are obtained by a polycondensation step using 35% to 60% by mass of at least one mono-fatty acid relative to the total weight of the alkyd resin (A).

[0206] By "mono-fatty acid" is meant a monocarboxylic acid, saturated or unsaturated, linear, branched or cyclic, optionally in its esterified form such as Ci-C7 alkyl esters or in anhydride form, comprising from 8 to 40 atoms, in particular from 8 to 32 atoms, and more preferably from 8 to 24 carbon atoms.

[0207] In the composition of the invention, when at least one monocarboxylic acid is implemented, then it is necessarily distinct from the monocarboxylic acids.

[0208] Preferably, the fatty monoacids do not carry an amine function and do not carry hydroxyl functions.

[0209] Among the mono-fatty acids that can be used in the context of the invention, the following may be mentioned, alone or in mixture: - saturated fatty acids such as caprylic acid, 2-ethylhexanoic acid, 4,5-dimethylhexanoic acid, 2-heptylheptanoic acid, 3,5,5-trimethylhexanoic acid, octanoic acid, isooctanoic acid, nonanoic acid, decanoic acid, isononanoic acid, lauric acid, tridecanoic acid, myristic acid, palmitic acid, stearic acid, isostearic acid, arachidic acid, behenic acid, cerotic (hexacosanoic) acid, - Cyclic fatty acids such as 3-cyclopentylpropionic acid, 3-cyclohexylpropionic acid, cyclohexylacetic acid, 4-cyclohexylbutyric acid, - Unsaturated fatty acids such as caproleic acid, undecylenic acid, dodecylenic acid, myristoleic acid, palmitoleic acid, oleic acid, linoleic acid, linolenic acid, elaidic acid, gondoic acid, erucic acid.

[0210] Preferably, the fatty acids are selected from octanoic acid, lauric acid, oleic acid, isostearic acid such as that marketed by CRODA under the name PRISORINE 3505-LQ-(GD), and more particularly isostearic acid.

[0211] According to another embodiment, the alkyd resins (A) are obtained by a polycondensation step using 37% to 59% by mass, more preferably 40% to 58% by mass of at least one mono-fatty acid relative to the total weight of the alkyd resin (A).

[0212] According to a particular embodiment, the alkyd resin(s) (A) are obtained by one-step polycondensation of: - 0% to 12% by mass, preferably 0% to 10% by mass of at least one diol; and - 20% to 50% by mass of at least one compound containing at least 3 alcohol functions; - 10% to 30% mass of at least one dicarboxylic acid compound; - 0% to 17% mass of at least one compound containing at least 3 carboxylic acid functions; - 0% to 10% by mass, preferably 0% by mass, of at least one monocarboxylic acid compound; and - 35% to 60% by mass, preferably 37% to 59% by mass, more preferably 40% to 58% by mass of at least one mono-fatty acid; mass percentages being expressed in relation to the total weight of the alkyd resin (A).

[0213] According to one embodiment, the alkyd resins (A) are obtained without the use of mono-fatty acids.

[0214] Polyacid compounds

[0215] The alkyd resin(s) (A) are obtained by a polycondensation step using 10% to 62% mass of at least one polyacid, the mass percentages being expressed in relation to the total weight of the alkyd resin (A).

[0216] By "polyacid" is meant an organic compound comprising 2 to 8 carboxylic acid functional groups, preferably 2 to 6 carboxylic acid functions, anhydride compounds also being part of polyacids within the meaning of the invention; and is understood in particular to include dicarboxylic acid compounds and compounds comprising at least 3 carboxylic acid functions of the invention.

[0217] Preferably, a polyacid does not include an amine function.

[0218] Preferably, the polyacids are saturated or unsaturated, linear, branched or cyclic organic compounds comprising from 2 to 40 carbon atoms, in particular from 6 to 36 carbon atoms and more preferably from 8 to 24 carbon atoms, optionally one or more non-adjacent oxygen atoms intercalated between two carbon atoms, and bearing from 2 to 8 carboxylic acid functions, preferably from 2 to 6 carboxylic acid functions.

[0219] Among polyacids, a distinction is made between diacids having two carboxylic acid functions and acids having at least 3 carboxylic acid functions, such as those having 3 to 6 carboxylic acid functions.

[0220] According to one embodiment, the alkyd resin(s) (A) are obtained by a polycondensation step using 10% to 62% by mass of at least one polyacid, said at least one polyacid containing 0% to 30% by mass of at least one dicarboxylic acid, the mass percentages being expressed in relation to the total weight of the alkyd resin (A).

[0221] The dicarboxylic acid(s) may be saturated or unsaturated aliphatic, linear or branched, cyclic, aromatic or non-aromatic, or in cyclic anhydride form, and may comprise from 2 to 40 carbon atoms, in particular from 3 to 36 carbon atoms, or even from 4 to 24 carbon atoms. When the diacids are in anhydride form, preferably, they comprise 8 to 12 carbon atoms.

[0222] Said cyclic anhydride of a diacid may in particular correspond to one of the following formulas:

[0223] [Chem.l]

[0224] in which groups A and B are, independently of each other, : - a hydrogen atom; - a carbon radical, aliphatic, saturated or unsaturated, linear, branched and / or cyclic, or aromatic, comprising from 1 to 16 carbon atoms, in particular from 2 to 10 carbon atoms, or even from 4 to 8 carbon atoms, in particular methyl or ethyl; - or A and B taken together form a ring comprising a total of 5 to 7, including 6 carbon atoms, saturated or unsaturated, or even aromatic.

[0225] Among the diacids or their anhydrides that may be used, the following may be mentioned, alone or in mixtures: - dicarboxylic acids such as Pripol 1009, decanedioic acid, dodecanedioic acid, cyclopropanedicarboxylic acid, cyclohexanedicarboxylic acid, cyclobutanedicarboxylic acid, naphthalene-1,4-dicarboxylic acid, naphthalene-2,3-dicarboxylic acid, naphthalene-2,6-dicarboxylic acid, suberic acid, oxalic acid, malonic acid, succinic acid, phthalic acid, terephthalic acid, isophthalic acid, pimelic acid, sebacic acid, azelaic acid, homophthalic acid, adipic acid, fumaric acid, maleic acid, muconic acid, itaconic acid.

[0226] Preferably, the diacid(s) are chosen from: sebacic acid, adipic acid, homophthalic acid, and mixtures thereof.

[0227] According to one embodiment, the alkyd resin(s) (A) are obtained by a polycondensation step using 10% to 62% by mass of at least one polyacid, said at least one polyacid containing 10% to 30% by mass of at least one dicarboxylic acid, the mass percentages being expressed in relation to the total weight of the alkyd resin (A).

[0228] According to one embodiment, the alkyd resin(s) (A) are obtained by polycondensation of: - 0% to 12% by mass, preferably 0% to 10% by mass of at least one diol; - 20% to 50% by mass of at least one compound containing at least 3 alcohol functions; - 10% to 30% mass, preferably 12% to 29% mass, of at least one dicarboxylic acid compound, preferably chosen from sebacic acid, adipic acid, homophthalic acid, and mixtures thereof; - 0% to 17% mass of at least one compound containing at least 3 carboxylic acid functions; - 0% to 10% by mass, preferably 0%, of at least one monocarboxylic acid compound; and - 35% to 60% mass of at least one mono-fatty acid, the mass percentages being expressed in relation to the total weight of the alkyd resin (A).

[0229] According to another embodiment, the alkyd resin(s) (A) are obtained by polycondensation of: -10% to 30% by mass, preferably 20% to 30% by mass of at least one diol; - 0% to 12% by mass, preferably 0% by mass, of at least one compound comprising at least 3 alcohol functions; - 0% to 12% by mass, preferably 0% by mass, of at least one dicarboxylic acid compound; - 20% to 50% by mass of at least one compound containing at least 3 carboxylic acid functions; - 0% to 20% by mass, preferably 0% by mass, of at least one monocarboxylic acid compound; and - 35% to 60% mass of at least one fatty alcohol, of which at least one contains at least one ethylenic unsaturation; mass percentages being expressed in relation to the total weight of the alkyd resin (A).

[0230] According to one embodiment, the alkyd resin(s) (A) are obtained without the use of dicarboxylic acid.

[0231] The alkyd resin(s) (A) are obtained by a polycondensation step using 10% to 62% by mass of at least one polyacid, said at least one polyacid containing 0% to 50% by mass of at least one compound comprising at least 3 carboxylic acid functions, the mass percentages being expressed in relation to the total weight of the alkyd resin (A).

[0232] By "acid having at least 3 carboxylic acid functions", we mean a polycarboxylic acid, saturated or unsaturated, or even aromatic, linear, branched or cyclic, comprising at least 3 carboxylic groups COOH, such as those having 3 to 6 carboxylic acid functions, in particular 3 to 5 COOH groups.

[0233] The acid(s) comprising at least 3 carboxylic acid functions may in particular be chosen from linear, branched and / or cyclic, saturated acids or unsaturated, or even aromatic, comprising 6 to 54, especially 6 to 40, carbon atoms, and even better 6 to 24 carbon atoms.

[0234] Among acids having at least 3 carboxylic acid functions, the following may preferably be mentioned: - tricarboxylic acids such as cyclohexanetricarboxylic acid, trimellitic acid, 1,2,3-benzenetricarboxylic acid, 1,3,5-benzenetricarboxylic acid; citric acid, tetracarboxylic acids such as butanetetracarboxylic acid, pyromellitic acid and their mixtures.

[0235] Preferably, the acid or acids comprising at least 3 carboxylic acid functions is citric acid.

[0236] According to another embodiment, the alkyd resin(s) (A) are obtained by polycondensation of: - 0% to 12% mass of at least one diol; - 20% to 50% by mass of at least one compound containing at least 3 alcohol functions; - 10% to 30% mass of at least one dicarboxylic acid compound; - 0% to 17% by mass, preferably 0% by mass, of at least one compound comprising at least 3 carboxylic acid functions; - 0% to 10% by mass, preferably 0% by mass, of at least one monocarboxylic acid compound; and - 35% to 60% by mass of at least one mono-fatty acid, mass percentages being expressed in relation to the total weight of the alkyd resin (A).

[0237] According to yet another embodiment, the alkyd resin(s) (A) are obtained by polycondensation of: - 10% to 30% mass of at least one diol; - 0% to 12% mass of at least one compound containing at least 3 alcohol functions; - 0% to 12% mass of at least one dicarboxylic acid compound; - 20% to 50% by mass of at least one compound containing at least 3 carboxylic acid functions; - 0% to 20% by mass of at least one monocarboxylic acid compound; and - 35% to 60% by mass, preferably 40% to 59% by mass, more preferably 45% to 55% by mass of at least one fatty alcohol, of which at least one contains at least one ethylenic unsaturation, preferably a single fatty alcohol, more preferably oleic alcohol.

[0238] the mass percentages being expressed in relation to the total weight of the alkyd resin (A).

[0239] According to one embodiment, the alkyd resin(s) (A) are obtained without the use of a compound comprising at least 3 carboxylic acid groups. Special polyesters

[0240] Various processes for the preparation of polycondensates have been described, notably by Witzeman et al. in the Journal of Coatings Technology, Vol. 62, no. 789, p. 101-112 (1990) or in Self-Healable Covalently Adaptable Networks Based on Disulfide Exchange, Polymers 2022, 14, 3953.

[0241] According to the invention, a polyester of formula (I) can be easily prepared, in a single synthesis step from alkyd resins (A) themselves obtained via a polycondensation reaction.

[0242] The present invention relates, according to one of its aspects, to a polyester of the following formula (I) comprising at least two acetoacetate functions, as well as its optical, geometric and / or solvated isomers, such as hydrates, or a composition containing it or them: (Z)-[OC(O)-C(Ra)(Rb)-C(O)-R4]u(I) formula (I) in which: - u is an integer greater than 2; - R4 represents a monovalent hydrocarbon radical in C1 to C6, linear or branched, saturated or unsaturated, preferably a (Ci-C4)alkyl group, in particular methyl or tert-butyl, more preferably methyl; - Ra and Rb, whether identical or different, represent a hydrogen atom or a (Ci-C4)alkyl group, preferably a hydrogen atom; and - Z denotes a multivalent radical derived from: I) of an alkyd resin (Al) obtained by polycondensation of: -10% to 62% by mass, preferably 10% to 42% by mass of at least one polyol; - 10% to 62% by mass, preferably 10% to 42% by mass of at least one polyacid; and - 35% to 60% by mass of at least one fatty alcohol, of which at least one contains at least one ethylenic unsaturation, relative to the total weight of the alkyd resin (Al); or II) of an alkyd resin (A2) obtained by polycondensation of: - 10% to 62% mass of at least one polyol, said at least one polyol being or comprising at least dipentaerythritol; - 10% to 62% by mass of at least one polyacid; and - 35% to 60% by mass of at least one mono-fatty acid; relative to the total weight of the alkyd resin (A2): OR III) of an alkyd resin (A3) obtained by polycondensation of: - 10% to 62% mass of at least one polyol, said at least one polyol being xylitol or comprising at least xylitol; - 10% to 62% by mass of at least one polyacid; and - 35% to 60% by mass of at least one mono-fatty acid; relative to the total weight of the alkyd resin (A3); Or ; IV) of an alkyd resin (A4) obtained by polycondensation of: - 10% to 62% mass of a mixture of at least two polyols, said mixture not containing dipentaerythritol or xylitol; - 10% to 62% by mass of at least one polyacid; and - 35% to 60% by mass of at least one mono-fatty acid; relative to the total weight of the alkyd resin (A4); Or V) of an alkyd resin (A5) obtained by polycondensation of: - 10% to 62% mass of a single polyol other than pentaerythritol and xylitol; - 10% to 62% by mass of at least one polyacid; and - 35% to 60% by mass of a mixture of at least two mono-fatty acids; relative to the total weight of the alkyd resin (A5); Or VI) of an alkyd resin (A6) obtained by polycondensation of: - 10% to 62% mass of a polyol other than dipentaerythritol and xylitol; - 10% to 62% by mass of at least one polyacid; and - 35% to 60% by mass of a mono-fatty acid other than oleic acid; relative to the total weight of the alkyd resin (A6); Or VII) of an alkyd resin (A7) obtained by polycondensation of: - 10% to 62% by mass, preferably 10% to 42% by mass of at least one polyol; - 10% to 62% by mass, preferably 10% to 42% by mass, of at least one polyacid, at least one of which contains at least one ethylenic unsaturation; and - 35% to 60% by mass of at least one saturated fatty alcohol; relative to the total weight of the alkyd resin (A7).

[0243] Preferably, the PI polyesters are obtained from alkyd (Al) resins themselves obtained by one-step polycondensation of: - 0% to 12% mass of at least one compound containing at least 3 alcohol functions; - 10% to 30% mass of at least one diol; - 0% to 12% mass of at least one dicarboxylic acid compound; - 20% to 50% by mass of at least one compound containing at least 3 carboxylic acid functions; - 0% to 20% by mass of at least one monocarboxylic acid compound; and - 35% to 60% by mass of at least one fatty alcohol, of which at least one contains at least one ethylenic unsaturation, relative to the total weight of the alkyd resin (Al).

[0244] More preferably, PI polyesters are obtained from alkyd (Al) resins themselves obtained by one-step polycondensation of: - 10% to 30% by mass, preferably 15% to 27% by mass, more preferably 20% to 25% by mass of at least one diol, said at least one diol being or comprising at least 1,10-decanediol; - 20% to 50% by mass, preferably 21% to 40% by mass, more preferably 21% to 30% by mass of at least one compound comprising at least 3 carboxylic acid functions, said at least one compound comprising at least 3 carboxylic acid functions being or comprising at least citric acid; - 35% to 60% mass of at least one fatty alcohol, said at least one fatty alcohol being or comprising at least oleic alcohol, more preferably being oleic alcohol.

[0245] Even more preferably, the PI polyester is that obtained in example 6.3.

[0246] Preferably, the P2 polyesters are obtained from alkyd resins (A2) themselves obtained by one-step polycondensation of: - 10% to 62% by mass, preferably 10% to 50% by mass, of at least one polyol, said polyol being or comprising at least dipentaerythritol; - 10% to 62% by mass, preferably 10% to 50% by mass, more preferably 10% to 30% by mass, of at least one dicarboxylic acid compound and / or compound comprising at least 3 carboxylic acid functions, preferably at least one dicarboxylic acid compound; - 35% to 60% mass of at least one mono-fatty acid, relative to the total weight of the alkyd resin (A2).

[0247] More preferably, P2 polyesters are obtained from alkyd resins (A2) themselves obtained by one-step polycondensation of: - 0% to 12% by mass, preferably 0% to 10% by mass more preferably 0% to 8% mass of at least one diol, preferably a single diol, more preferably Pripol 2033; - 20% to 50% by mass, preferably 25% to 50% of at least one compound comprising at least 3 alcohol functions, said at least one compound comprising at least 3 alcohol functions being or comprising at least dipentaerythritol, of preferably said at least one compound comprising at least 3 alcohol functions being dipentaerythritol or a mixture of dipentaerythritol and erythritol; - 10% to 30% mass of at least one dicarboxylic acid compound, preferably a mixture of dicarboxylic acid compounds, more preferably a mixture of adipic acid and homophthalic acid; - 0% to 17% by mass, preferably 0% by mass, of at least one compound comprising at least 3 carboxylic acid functions; - 0% to 10% by mass, preferably 0% by mass, of at least one monocarboxylic acid compound; and - 35% to 60% by mass of at least one mono-fatty acid, preferably chosen from octanoic acid, oleic acid, lauric acid, isostearic acid, more preferably a mixture of lauric acid and isostearic acid or a mixture of octanoic acid and oleic acid, relative to the total weight of the alkyd resin (A2).

[0248] Even more preferably, the P2 polyesters are those obtained in examples 4.2 and 5.2.

[0249] Preferably, the P3 polyesters are obtained from alkyd resins (A3) themselves obtained by one-step polycondensation of: - 10% to 50% by mass of at least one compound comprising at least 3 alcohol functional groups, said at least one compound comprising at least 3 alcohol functional groups being or comprising at least xylitol; and - 10% to 30% by mass of at least one dicarboxylic acid compound; and - 35% to 60% by mass of at least one mono-fatty acid,

[0250] relative to the total weight of the alkyd resin (A3).

[0251] More preferably, P3 polyesters are obtained from alkyd resins (A3) themselves obtained by one-step polycondensation of: - 0% to 12% by mass, preferably 0% by mass, of at least one diol; - 20% to 50% mass of at least one compound comprising at least 3 alcohol functions, said at least one compound comprising at least 3 alcohol functions being or comprising at least xylitol, preferably said at least one compound comprising at least 3 alcohol functions being xylitol; - 10% to 30% mass of at least one dicarboxylic acid compound, preferably a single dicarboxylic acid compound, more preferably sebacic acid; - 0% to 17% by mass, preferably 0% by mass, of at least one compound containing at least 3 carboxylic acid functions; and - 0% to 10% by mass, preferably 0% by mass, of at least one monocarboxylic acid compound; and - 35% to 60% by mass of at least one mono-fatty acid, preferably chosen from octanoic acid, oleic acid, lauric acid, isostearic acid, more preferably a single fatty acid, even more preferably octanoic acid.

[0252] relative to the total weight of the alkyd resin (A3).

[0253] Even more preferably, the P3 polyesters are those obtained in example 3.2.

[0254] Preferably, the P4 polyesters are obtained from alkyd resins (A4) themselves obtained by one-step polycondensation of: - 10% to 62% mass of a mixture of at least two compounds each comprising at least 3 alcohol functions, said mixture not containing dipentaerythritol or xylitol; - 10% to 30% mass of at least one dicarboxylic acid compound; - 35% to 60% mass of at least one mono-fatty acid, relative to the total weight of the alkyd resin (A4).

[0255] More preferably, P4 polyesters are obtained from alkyd resins (A4) themselves obtained by one-step polycondensation of: - 0% to 12% by mass, preferably 0% by mass, of at least one diol; - 20% to 50% mass of a mixture of at least two compounds each comprising at least 3 alcohol functions, said mixture not containing dipentaerythritol or xylitol; - 10% to 30% mass of at least one dicarboxylic acid compound; - 0% to 17% mass of at least one compound containing at least 3 carboxylic acid functions; - 0% to 10% by mass of at least one monocarboxylic acid compound; and - 35% to 60% by mass of at least one mono-fatty acid;

[0256] relative to the total weight of the alkyd resin (A4).

[0257] Even more preferably, P4 polyesters are obtained from alkyd resins (A4) themselves obtained by one-step polycondensation of: - 0% to 12% by mass, preferably 0% by mass, of at least one diol; - 20% to 50% mass of a mixture of at least two compounds chosen from glycerol, trimethylolpropane, pentaerythritol (tetramethylolmethane), erythritol, diglycerol, sorbitol, mannitol; - 10% to 30% mass of at least one dicarboxylic acid compound; - 0% to 17% mass of at least one compound containing at least 3 carboxylic acid functions; - 0% to 10% by mass of at least one monocarboxylic acid compound; and - 35% to 60% by mass of at least one mono-fatty acid; relative to the total weight of the alkyd resin (A4).

[0258] Preferably, the P5 polyesters are obtained from alkyd resins (A5) themselves obtained by one-step polycondensation of: - 10% to 50% mass of a single compound comprising at least 3 alcohol functions, said compound being different from pentaerythritol and xylitol; - 10% to 30% mass of at least one dicarboxylic acid compound; - 35% to 60% by mass of a mixture of at least two mono-fatty acids; relative to the total weight of the alkyd resin (A5).

[0259] More preferably, P5 polyesters are obtained from alkyd resins (A5) themselves obtained by one-step polycondensation of: - 0% to 12% by mass, preferably 0% by mass, of at least one diol; - 20% to 50% mass of a single compound comprising at least 3 alcohol functions, said compound being different from dipentaerythritol and xylitol; - 10% to 30% mass of at least one dicarboxylic acid compound; - 0% to 17% by mass, preferably 0% by mass, of at least one compound comprising at least 3 carboxylic acid functions; - 0% to 10% by mass, preferably 0% by mass, of at least one monocarboxylic acid compound; and - 35% to 60% by mass of a mixture of at least two mono-fatty acids, preferably a mixture of two fatty acids, relative to the total weight of the alkyd resin (A5).

[0260] Even more preferably, P5 polyesters are obtained from alkyd resins (A5) themselves obtained by one-step polycondensation of: - 0% to 12% by mass, preferably 0% by mass, of at least one diol; - 20% to 50% mass of a single compound comprising at least 3 alcohol functions, said compound being chosen from glycerol, pentaerythritol, erythritol, diglycerol; and more preferably designating pentaerythritol; - 10% to 30% mass of at least one dicarboxylic acid compound; - 0% to 17% by mass, preferably 0% by mass, of at least one compound comprising at least 3 carboxylic acid functions; - 0% to 10% by mass, preferably 0% by mass, of at least one monocarboxylic acid compound; and - 35% to 60% by mass of a mixture of at least two mono-fatty acids, preferably a mixture of two fatty acids, relative to the total weight of the alkyd resin (A5).

[0261] Preferably, the P6 polyesters are obtained from alkyd resins (A6) themselves obtained by one-step polycondensation of: - 10% to 50% mass of a polyol other than dipentaerythritol and other than xylitol; - 10% to 30% by mass of at least one dicarboxylic acid compound; and - 35% to 60% by mass of a mono-fatty acid, said at least one fatty acid being different from oleic acid; relative to the total weight of the alkyd resin (A6).

[0262] More preferably, P6 polyesters are obtained from alkyd resins (A6) themselves obtained by one-step polycondensation of: - 0% to 12% by mass, preferably 0% by mass, of at least one diol; - 20% to 50% mass of a compound containing at least 3 alcohol functions other than dipentaerythritol and xylitol; - 10% to 30% mass of at least one dicarboxylic acid compound; - 0% to 17% by mass, preferably 0% by mass, of at least one compound comprising at least 3 carboxylic acid functions; - 0% to 10% by mass, preferably 0% by mass, of at least one monocarboxylic acid compound; and - 35% to 60% by mass of a mono-fatty acid other than oleic acid; relative to the total weight of the alkyd resin (A6).

[0263] Even more preferably, P6 polyesters are obtained from alkyd resins (A6) themselves obtained by one-step polycondensation of: - 20% to 50% mass of a compound comprising at least 3 alcohol functions chosen from triols and tetraols, preferably chosen from glycerol, pentaerythritol, erythritol, diglycerol; and more preferably chosen from pentaerythritol; - 10% to 30% mass of at least one dicarboxylic acid compound, preferably chosen from sebacic acid, homophthalic acid, Pripol 1009, malonic acid, succinic acid, itaconic acid, more preferably chosen from sebacic acid, homophthalic acid, and their mixtures, even more preferably a single dicarboxylic acid compound chosen from sebacic acid, homophthalic acid; - 35% to 60% mass of a mono-fatty acid chosen from isostearic acid, octanoic acid, lauric acid, palmitic acid, myristoleic acid, more preferably chosen from isostearic acid, relative to the total weight of the alkyd resin (A6).

[0264] Better still, the P6 polyesters are those obtained in examples 1.2 and 2.2.

[0265] Preferably, the P7 polyesters are obtained from alkyd resins (A7) themselves- same as those obtained by one-step polycondensation of: - 10% to 30% mass of at least one diol; - 0% to 12% mass of at least one compound containing at least 3 alcohol functions; - 0% to 12% mass of at least one dicarboxylic acid compound; - 20% to 50% by mass of at least one compound containing at least 3 carboxylic acid functions; - 0% to 20% by mass of at least one monocarboxylic acid compound; and - 35% to 60% by mass of at least one fatty alcohol, of which at least one contains at least one ethylenic unsaturation, relative to the total weight of the alkyd resin (A7).

[0266] More preferably, P7 polyesters are obtained from alkyd resins (A7) themselves obtained by one-step polycondensation of: - 10% to 30% by mass, preferably 15% to 27% by mass, more preferably 20% to 25% by mass of at least one diol, said at least one diol being or comprising at least 1,10-decanediol; - 20% to 50% by mass, preferably 21% to 40% by mass, more preferably 21% to 30% by mass of at least one compound comprising at least 3 functional groups carboxylic acid, said at least one compound comprising at least 3 carboxylic acid functions being or comprising at least citric acid; and - 35% to 60% mass of at least one fatty alcohol, said at least one fatty alcohol being or comprising at least oleic alcohol, more preferably being oleic alcohol. Alkyd resins (B)

[0267] The alkyd resins (B) used in the preparation of the polyesters of formula (I) can be prepared in 2 successive steps, the first step leading to alkyd resins (A) containing ethylenic unsaturations.

[0268] Thus, alkyd resins (B) can be obtained in 1 step from alkyd resins (A) containing ethylenic unsaturations.

[0269] In particular, an alkyd resin (B) used in the preparation of polyesters of formula (I) is characterized in that it is obtained from the reaction of an alkyd resin (A) containing ethylenic unsaturations with at least one (poly)hydroxy thiol, said alkyd resin (A) being obtained via: a) a first step by polycondensation of: - 0% to 12% mass of at least one compound containing at least 3 alcohol functions; - 10% to 30% mass of at least one diol; - 0% to 12% mass of at least one dicarboxylic acid compound; - 20% to 50% by mass of at least one compound containing at least 3 carboxylic acid functions; - 35% to 60% by mass of at least one fatty alcohol; and - 0% to 20% by mass of at least one monocarboxylic acid compound, the mass percentages being expressed relative to the total weight of the alkyd resin (A), it being understood that at least one of the dicarboxylic acid compounds and compounds comprising at least 3 carboxylic acid functions, and / or at least one of the fatty alcohols, contains at least one ethylenic unsaturation; followed by b) a second step consisting of a thiol-ene reaction of all or part of the ethylenic unsaturations of the alkyd resin (A) obtained at the end of step a), with at least one (poly)hydroxy thiol, preferably of the following formula (Fl): RD-SH (Fl) in which RD represents a linear or branched C2-CiO hydrocarbon radical substituted by at least one hydroxy radical, preferably substituted by one or two hydroxy radicals.

[0270] Preferably, the alkyd resin(s) (A) containing ethylenic unsaturations obtained at the end of step a) have a hydroxyl number of less than 50 mg KOH / g.

[0271] According to a preferred embodiment, the alkyd resin(s) (A) containing ethylenic unsaturations are obtained by one-step polycondensation a) of: - 0% to 12% mass of at least one compound comprising at least 3 alcohol functions; - 10% to 30% mass of at least one diol; - 0% to 12% by mass of at least one dicarboxylic acid compound, preferably saturated; - 20% to 50% by mass of at least one compound comprising at least 3 carboxylic acid functions, preferably saturated; - 35% to 60% by mass of at least one fatty alcohol; and - 0% to 20% mass of at least one monocarboxylic acid compound, the mass percentages being expressed in relation to the total weight of the alkyd resin (A), it being understood that at least one of the fatty alcohols contains at least one ethylenic unsaturation.

[0272] According to this embodiment, preferably, dicarboxylic acid compounds and compounds comprising at least 3 carboxylic acid functions are saturated. Also according to this embodiment, preferably, the acid value of the alkyd resin (A) obtained at the end of step a) is between 0 and 15 mg KOH / g.

[0273] Preferably, the fatty alcohol(s) comprising at least one ethylenic unsaturation implemented in step a) are chosen from 9-decen-l-ol, citronellol, oleic alcohol, linoleic alcohol and mixtures thereof, more preferably oleic alcohol.

[0274] The (poly)hydroxy thiol(s) implemented in step b) may be selected from 2-mercaptoethanol, 3-mercapto-l-propanol, 6-mercapto-l-hexanol, 4-mercapto-l-butanol, 3-mercapto-3-methylbutanol, 3-mercapto-2-butanol, 3-mercapto-1,2-propanediol.

[0275] Preferably, only one (poly)hydroxy thiol is implemented in step b), more preferably the (poly)hydroxy thiol is 3-mercapto-l,2 propanediol.

[0276] At the end of step b), an alkyd resin (B) is obtained bearing hydroxyl groups and preferably the hydroxyl number of (B) is greater than 50 mg KOH / g of alkyd resin (B), more preferably greater than 100 mg KOH / g of alkyd resin (B).

[0277] PREPARATION PROCESS

[0278] Generally, the -C(O)-C(Ra)(Rb)-C(O)-R4 radical-bearing polyesters according to the invention are prepared in one step from alkyd resin (A) or alkyd resin (B) as described above by reacting all or part of the hydroxyl functions of the alkyd resin (A) or (B), for example via a (trans)esterification reaction with a Gp-C(O)-C(Ra)(Rb)-C(O)-R4 ester, in which Gp denotes a group starting preferably from a hydroxy radical or an (Cl-C4)alkoxy radical, such as methoxy, ethoxy, isobutoxy or t-butoxy, to form -OC(O)-C(Ra)(Rb)-C(O)-R4 esters with Ra, Rb and R4 as defined above.

[0279] Preferably, Ra and Rb are identical and denote a hydrogen atom.

[0280] Preferably, R4 denotes a methyl radical.

[0281] According to a preferred embodiment, Gp-C(O)-C(Ra)(Rb)-C(O)-R4 designates an ester selected from ethyl acetoacetate, ethyl 2-methylacetoacetate, tert-butyl acetoacetate, preferably tert-butyl acetoacetate.

[0282] According to a preferred embodiment, at least 20% of the hydroxyl radicals of the alkyd resin (A) or (B) are transformed into -OC(O)-C(Ra)(Rb)-C(O)-R4 esters, preferably at least 30%, more preferably at least 40%, even more preferably at least 50%, better at least 80%.

[0283] According to a preferred embodiment, the hydroxyl number of the polyesters according to the invention is less than 50 mg KOH / g of polyester.

[0284] According to another aspect of the invention, the invention relates to a process for preparing polyester compounds of formula (I) comprising at least two acetoacetate functions as described above, comprising at least one reaction step of all or part of the hydroxyl functions of at least one alkyd resin (Al), (A2), (A3), (A4), (A5), (A6) or (A7), preferably via a (trans)esterification reaction with a Gp-C(O)-C(Ra)(Rb)-C(O)-R4 ester, in which Gp denotes a group starting preferably from a hydroxy radical or an (Ci-C4)alkoxy radical, such as methoxy, ethoxy, isobutoxy or t-butoxy, to form -OC(O)-C(Ra)(Rb)-C(O)-R4 esters with Ra, Rb and R4 being as defined above.

[0285] In particular the polyesters of examples 1.2, 2.2, 3.2, 4.2 and 5.2 are obtained in one step from alkyd resins (A).

[0286] Preferably, polyesters derived from alkyd resins (Al) are prepared in 2 steps, the first step being the thiolene reaction of all or part of the ethylenic unsaturations of the alkyd resin (Al) with at least one (poly)hydroxy thiol as described above to lead to a resin (Bl), the second step being the reaction of all or part of the hydroxyl functions of the alkyd resin (A) or (B), for example via a (trans)esterification reaction with a Gp-C(O)-C(Ra)(Rb)-C(O)-R4 ester.

[0287] More preferably, the polyester of example 6.3 is obtained according to this 2-step process.

[0288] Crosslinking Agent

[0289] According to a particular embodiment, the treatment process according to the invention as described above comprises the application to keratin fibers, preferably hair, of (i) at least one polyester of formula (I) as defined above, and (ii) at least one crosslinking agent.

[0290] For the purposes of the invention, the term "crosslinking agent", also referred to as "R", designates a compound capable of forming with at least one acetoacetate function of the polyester(s) of formula (I) used in the treatment process according to the invention:

[0291] - at least one covalent bond, - at least one donor-acceptor (dative) bond, and / or - at least one coordination bond,

[0292] and thus to crosslink this or these compound(s).

[0293] Preferably, the term “crosslinking agent”, also referred to as “R”, designates a compound capable of establishing at least one covalent bond with an acetoacetate function of the polyester(s) of formula (I) used in the treatment process according to the invention and thus crosslinking this or these compound(s).

[0294] For the purposes of the present invention, it is understood that the terms “crosslinking agent” and “crosslinking agent” are equivalent.

[0295] Compositions “C2”, “C3” and “C4” as defined above contain at least ii) a crosslinking agent. The compositions of the invention may comprise an oily phase, an aqueous phase, or may be in the form of a direct or reverse emulsion. Composition “C4” may be an aqueous composition.

[0296] According to one aspect, the treatment process of the invention uses a composition called "C3", in particular cosmetic for the treatment of fibers keratin, in particular for the care, styling and / or coloring of keratin fibers, preferably hair, i) at least one polyester of formula (I), as defined above and below, ii) at least one crosslinking agent, in particular as defined above and below, and iv) at least one cosmetic active, in particular as defined above and below.

[0297] The crosslinking agent(s) ii) are preferably present in a mass content ranging from 0.2% to 60% by weight, in particular ranging from 0.5% to 40% by weight, and more particularly from 1% to 35% by weight, even more particularly from 1% to 30% relative to the total weight of the composition containing them.

[0298] In particular, in compositions “C2” or “C3”, the crosslinking agent(s) ii) and the polyester(s) i) as defined above are preferably present in a mass content ranging from 1% to 35% by weight, relative to the total weight of the composition comprising them.

[0299] When the treatment process involves several steps including a step of implementing one or more formula (I) polyesters without crosslinker, the formula (I) polyester(s) may be implemented alone (pure), or in a "Cl" composition as described above.

[0300] More specifically, the crosslinking agent(s) ii) suitable for the invention may be selected from compounds with amine, thiol, acrylate and / or carbonyl functional groups such as a ketone or aldehyde functional group, or mixtures thereof. A crosslinking agent R may also refer to a metal alkoxide. In a particular embodiment, the crosslinking agent(s) do not contain metal salts.

[0301] Thus, according to a particular embodiment, the crosslinking agent(s) ii) are chosen from A) (poly)amine compounds, B) polythiol compounds, C) polyacrylates, D) metal alkoxides, E) polycarbonyl compounds, and mixtures thereof, preferably chosen from A) polyamine compounds, B) polythiol compounds, E) metal alkoxides, and mixtures thereof.

[0302] Polyamine, polythiol, polycarbonyl and polyacrylate compounds are defined as compounds comprising respectively at least two primary or secondary amine, thiol, carbonyl (such as a ketone or aldehyde) or acrylate functions.

[0303] Metal alkoxide compounds are defined below.

[0304] According to one embodiment, the process according to the invention uses a single crosslinking agent.

[0305] According to another embodiment, the process according to the invention uses several crosslinkers exclusively of the same family, namely several crosslinkers A) without crosslinker B), C), D), E), or several crosslinkers B) without crosslinker A), C), D), E), or several crosslinkers C) without crosslinker A), B), D), E), or several crosslinkers D) without crosslinking agent A), B), C), E), or several crosslinking agents E) without crosslinking agent A), B), C), D).

[0306] According to yet another embodiment, the process according to the invention uses at least two crosslinkers belonging to distinct families such as for example at least one crosslinker A) with at least one crosslinker B) and / or C) and / or D) and / or E), or at least one crosslinker B) with at least one crosslinker A), C), D), E) or at least one crosslinker C) with at least one crosslinker A), B), D), E), or at least one crosslinker D) with at least one crosslinker A), B), C), E), or at least one crosslinker E) with at least one crosslinker A), B), C), D). A) Polyamine compounds

[0307] According to a preferred embodiment, the process according to the invention comprises the application of at least one crosslinking agent R selected from (poly)amine compounds. The (poly)amine compound is in particular selected from polyamine compounds having several primary and / or secondary amine groups or from amino alkoxysilanes having only one primary and / or secondary amine group, and more particularly from amino alkoxysilane compounds having only one primary and / or secondary amine group, diamine compounds, triamine compounds, and mixtures thereof.

[0308] The (poly)amine 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 selected from -O-, -S-, -Si(R')2-, -N(R”)- preferably -O-, -Si(R')2-, or their combinations such as -Si(R')2-O- or -O-Si(R')2-, with R', identical or different, representing a (Ci-C4)alkyl group such as methyl, and R” representing a hydrogen atom or a (Ci-C4)alkyl group, preferably a hydrogen atom.

[0309] By "non-polymer compound" is meant a compound that is not directly obtained by a polymerization reaction of monomers.

[0310] Examples of (poly)amine compounds include N-methyl-1,3-diaminopropane, N-propyl 1,3-diaminopropane, N-isopropyl 1,3-diaminopropane, N-cyclohexyl 1,3-diaminopropane, 2-(3-aminopropylamino)ethanol, 3-(2-aminoethyl)aminopropylamine, bis(3-aminopropyl)amine, methyl bis(3-aminopropyl)amine, N-(3-aminopropyl)-1,4-diaminobutane, N,N-dimethyldipropylene triamine, 1,2-bis(3-aminopropylamino)ethane, N,N'-bis(3-aminopropyl)-1,3-propanediamine, ethylenediamine, 1,3-propylenediamine, 1,4-butylenediamine, lysine, cystamine, xylenediamine, tris(2-aminoethyl)amine, l,3-bis(aminomethyl)cyclohexane, the 1,4-bis(aminomethyl)cyclohexane, diaminopropanol, 4,7,10-Trioxa-1,13-tridecanediamine, spermidine and C36-alkylenediamines (respectively Priamine™ 1071, 1073, 1074, 1075), preferably spermidine and / or 4,7,10-Trioxa-l,13-tridecanediamine.

[0311] 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).

[0312] The (poly)amine compound(s) may be chosen from among the amino alkoxysilanes, in particular those of formula R'iSi(OR'2)z(R'3)x, in which:

[0313] - R'i is a linear or branched, saturated Ci-C6 hydrocarbon chain or unsaturated, cyclic or acyclic substituted by a group chosen from the primary amine group NH2 or secondary amine group -N(H)R with R representing an alkyl in CrC4, an aryl, a benzyl substituted by an amino group or by an aminoalkyl group in Ci-C4; R can be interrupted in its chain by a heteroatom (O, S, NH) or a carbonyl group C(O), R being linked to the silicon atom directly via a carbon atom,

[0314] - R'2 and R'3, whether identical or different, represent a linear (Ci-C6)alkyl group or branched,

[0315] - z denotes an integer from 1 to 3, and

[0316] - x denotes an integer from 0 to 2,

[0317] with z + x = 3.

[0318] In particular, R is an acyclic chain. Preferably, R is a linear or branched, saturated or unsaturated C1-C6 hydrocarbon chain substituted with an amine group -NH2 or -N(H)R, where R represents a C1-C6 alkyl, a C3-C6 cycloalkyl, or a C6 aromatic. More preferably, R' is a linear saturated C1-C6 hydrocarbon chain substituted with an amine group NH2. Even more preferably, R' is a linear saturated C2-C4 hydrocarbon chain substituted with an amine group NH2.

[0319] In particular, R'2 represents an alkyl group comprising 1 to 4 carbon atoms, preferably R'2 represents a linear alkyl group comprising 1 to 4 carbon atoms, and more preferably R'2 represents the ethyl group.

[0320] 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.

[0321] In particular, the (poly)amine compound(s) are chosen from among the amino alkoxysilanes comprising only one primary and / or secondary amine group, of primary preference (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.

[0322] 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-aminopropyltriethoxysilane (APTES), in particular that marketed by Sigma Aldrich.

[0323] According to a particular embodiment of the invention, the (poly)amine compound(s) are diaminized, namely they contain two primary and / or secondary amine groups, preferably primary (NH2).

[0324] More specifically, they are chosen from compounds of formula (V) or (VI):

[0325] • ALK[(O-ALK')m-NH2]2 (V)

[0326] or

[0327] • H2N-ALK-Si(R')2-[O-Si(R')2]mO-Si(R)2-ALK'-NH2 (VI)

[0328] formulas (V) and (VI) in which:

[0329] - ALK and ALK', whether identical or different, represent a (Ci-C6)alkylene group, linear or branched, preferably linear, such as propylene,

[0330] - R', identical or different, represents an (Ci-C4)alkyl group, such as methyl,

[0331] - m represents an integer greater than or equal to 0, preferably the value of m is such that the average molecular weight by weight of the compound (V) or (VI) ranges from 500 g.mol1 to 55000 g.mol1.

[0332] 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.

[0333] The (poly)amine compound(s) which are diaminized are particularly diaminized polyethers in particular of formula H2N-ALK-O-[ALK'-O]m-ALK”-NH2 with ALK, ALK' and ALK”, identical or different representing a (Ci-C6)alkylene group, linear or branched, and m representing an integer greater than or equal to 0, such as 4,7,10-trioxa-l,13-tridecanediamine or the compounds known under the reference Jeffamine of the Huntsman company, and more particularly polyethylene glycol and / or polypropylene glycol a, co-diamine (with amine function at the end of the chain) such as those sold under the names Jeffamine D-230, D-400, D-2000, D-4000, ED-600, ED-9000, ED-2003.

[0334] According to a particular embodiment of the invention, the (poly)amine compound(s) are triamine, namely they contain three primary and / or secondary amine groups, preferably primary (NH2). More particularly, they are selected from triamine polyethers, notably those 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.

[0335] As (poly)amine compounds which are triamined, triamine 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 names Jeffamine T-403.

[0336] 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).

[0337] In this variant, the (poly)amine compound(s) are chosen from poly(meth)acrylates or poly(meth)acrylamides bearing primary or secondary amine functions, such as poly(3-aminopropyl)methacrylamide and poly(2-aminoethyl)methacrylate.

[0338] Preferably, the polyamine compounds are chosen from chitosans (in particular poly(D-glucosamine)), and polydimethylsiloxanes comprising primary amine groups at the end of the chain and / or on side chains.

[0339] 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 reference 408700 by Aldrich Chemical or under the trade name Lupasol by BASF, in particular with a molecular weight between 1,200 and 25,000; poly(allylamine), in particular that sold under reference 479136 by Aldrich Chemical; polyvinylamines and their copolymers, in particular with vinylamides, in particular vinylamine / vinylformamide copolymers such as those marketed under the name Lupamin® 9030 by BASF; polyamino acids having NH2 groups such as polylysine, in particular that sold by JNC Corporation (formerly Chisso); amino dextran, in particular that sold by the company CarboMer Inc;Polyvinyl amino alcohol, in particular that sold by CarboMer Inc., acrylamido(Ci-C6)alkylamine-based copolymers, notably acrylamidopropylamine-based; and poly(D-Glucosamine), for example, sold under the reference Kionutrime CSG® by Kytozyme.

[0340] According to a particular embodiment, polydimethylsiloxanes comprising primary amine groups at the end of the chain and / or on side chains are selected from the compounds of the following formula (VII):

[0341] Ra-Si(Rb)(Rc)-O-[Si(Rb)(Rc)-O]m-[Si(ALK1-NH2)(Ra)-O]n-Si(Rb)(Rc)-Ra(VII)

[0342] formula (VII) in which:

[0343] - Ra, identical or different, represents a hydroxy or (Ci-C4)alkyl group,

[0344] - Rb and Rc, identical or different, preferably identical, represent a group (Ci-C4)alkyl, such as methyl,

[0345] - ALK1 represents a (Ci-C6)alkylene group, linear or branched, possibly interrupted by a group N(H),

[0346] - m and n are integers greater than or equal to 1, preferably m and n are such that the The average molecular mass by weight of the compound of formula (VII) ranges from 1000 g.mol1 to 500000 g.mol1.

[0347] According to a preferred embodiment, 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 polydimethylsiloxane ranges from 1000 g.mol1 to 55000 g.mol1.

[0348] 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.

[0349] According to another variant, formula (VII) is such that Ra represents a hydroxyl or (CrC4)alkyl group, such as methyl, ALK1 represents a (C5-C6)alkylene group substituted by an NH group, preferably ALK1 represents -(CH2)3-N(H)-(CH2)2-, and m and n are such that the weight average molecular mass of the compound of formula (VI) ranges from 5000 g.mol1 to 500000 g.mol1.

[0350] As an amino polymer, polytetrahydrofuran (or polytetramethylene glycol) α, co-diamine, and polybutadienes α, co-diamine may also be cited.

[0351] According to a particular embodiment of the invention, the (poly)amine compounds are selected from hyperbranched polymers comprising at least one amino group and dendrimers bearing at least one amino group, such as PAMAM polyamidoamine dendrimers with an ethylenediamine core and a terminal amine function.

[0352] According to a preferred embodiment, the composition comprises a crosslinking agent R selected from (poly)amine compounds, in particular selected from chitosans, aminoalkoxysilanes, polydimethylsiloxanes comprising primary amine groups at the end of the chain or on side chains, amodimethicones, polyglucosamines, spermidine, and mixtures thereof.

[0353] More preferably, the composition comprises a crosslinking agent R selected from spermidine, chitosans, aminoalkoxysilanes and polydialkylsiloxanes comprising primary amine groups at the end of the chain or on side chains such as amodimethicones, and even more preferably selected from poly(D-Glucosamine), 3-aminopropyltriethoxysilane (APTES), 3-aminoethyltriethoxysilane (AETES), 3-aminopropylmethyldiethoxysilane, V-(2-aminoethyl)-3-aminopropyltriethoxysilane, spermidine, and polydimethylsiloxanes comprising terminal amino groups at the end of the chain, such as Bis-Cetearyl Amodimethicone. B) (Poly)thiol compounds

[0354] According to a preferred embodiment, the process according to the invention comprises the application of at least one crosslinking agent R selected from (poly)thiol compounds also called “(poly)mercapto”.

[0355] The (poly)thiol compound may in particular be organic or inorganic, preferably organic.

[0356] In a preferred embodiment, the (poly)thiol compound is siliconed, that is to say, it comprises one or more thiol groups, it also comprises at least one siloxane chain.

[0357] In a particular embodiment, the (poly)thiol compound is inorganic. Polythiol silicones are an example.

[0358] The (poly)thiol compound can in particular be chosen from among non-polymeric (poly)thiol compounds.

[0359] By "non-polymer compounds", in the context of the present invention, we mean compounds that are not directly obtained by a polymerization reaction of monomers.

[0360] According to one embodiment of the invention, the (poly)thiol compound(s) is organic, non-polymeric, and of formula (VIII) below, as well as its solvates, such as its hydrates:

[0361] L(SH)q (VIII)

[0362] formula (VIII) in which:

[0363] - q, represents an integer greater than or equal to 2, preferably q is between inclusively between 2 and 10, preferably between 2 and 5;

[0364] - L denotes a multivalent (at least divalent) group, in particular comprising between 1 and 500 carbon and / or silicon atoms, more particularly between 2 and 40 carbon and / or silicon atoms, even more particularly between 3 and 30 carbon and / or silicon atoms, preferably between 6 and 20 carbon atoms, linear or branched, saturated or unsaturated, or (hetero)cyclic, saturated or unsaturated; L being possibly interrupted and / or terminated by one or more heteroatoms or groups chosen from O, S, N, Si, C(X), and their combinations such as -O-, -OC(X)-, -N(R)-C(X)-, -Si(Rc)(Rd)-O- with R representing a hydrogen atom or a (Ci-C6)alkyl group, such as methyl; and / or L being possibly substituted by one or more groups chosen from: -N(Ra)Rb, and -(X')aC(X)-(X”)b-Ra; with X, X' and X”, identical or different, representing an oxygen atom, a sulfur atom, or an N(Rb) group; a and b being 0 or 1, preferably the sum of a + b is 1; Ra and Rb, whether identical or different, represent a hydrogen atom, or a (Ci-C6)alkyl, or aryl(Ci-C4)alkyl group, such as benzyl, preferably Ra and Rb represent a hydrogen atom; and Rc and Rd, whether identical or different, represent a (Ci-C6)alkyl, aryl(Ci-C4)alkyl or (Ci-C6)alkoxy group.

[0365] According to a particular embodiment of the invention, the (poly)thiol compound(s) are chosen from among polythiol compounds, in particular polythiol compounds comprising from 2 to 20 carbon atoms.

[0366] According to a preferred embodiment, the (poly)thiol compound(s) are non-polymeric, in particular of formula (VIII) defined above, in which q is an integer greater than or equal to 2, preferably q is an integer inclusively between 2 and 10, preferably between 2 and 5.

[0367] The (poly)thiol compound(s) suitable for the invention are preferably dithiol compounds.

[0368] Preferably, L denotes a multivalent C8-Ci8 radical, in particular a linear one. Preferably, the fat-soluble polythiol is a C8-Ci8 dithiol, in particular a linear one. Preferably, the C8-Ci8 chain is a hydrocarbon chain, that is to say, composed of carbon and hydrogen. In particular, the fat-soluble polythiol is a linear C8-Ci6 diol, in particular a C10-Ci4 diol. Examples of (poly)thiol compounds of formula (VII) include, in particular, 1,8-octanedithiol, 1,10-decanedithiol, 1,12-dodecanedithiol, 1,14-tetradecanedithiol, 1,16-hexadecanedithiol, and 1,18-octadecanedithiol. Preferably, 1,10-decanedithiol, 1,12-dodecanedithiol and / or 1,14-tetradecanedithiol are used, preferably 1,12-dodecanedithiol.

[0369] According to another particular embodiment of the invention, the (poly)thiol compound(s) is selected from thiol alkoxysiloxanes, such as those of formula (VIII') below:

[0370] R'1-Si(OR'2)z(R'3)x (VIII')

[0371] formula (VIII') in which:

[0372] - R' i is a linear or branched, saturated C1-C12 hydrocarbon chain or unsaturated, cyclic or acyclic, substituted by one or more groups chosen from among the thiol groups; and aryl, aryloxy, arylthio, arylamino, the aryl group being substituted by one or more thiol groups, or thiol(Ci-C6) alkyl, preferably thiol(Ci-C6) alkyl; and R\ is optionally interrupted in its hydrocarbon chain by one or more heteroatoms such as O, S, N, a carbonyl group C(O), or their association such as -C(O)-O- ester, or -C(O)-N(H)- amide, R\ being linked to the silicon atom directly via a carbon atom,

[0373] - R'2 and R'3, whether identical or different, represent an alkyl group, linear or branched, comprising from 1 to 6 carbon atom(s), preferably from 1 to 4 carbon atom(s), such as methyl,

[0374] - z denotes an integer from 1 to 3, and

[0375] - x denotes an integer from 0 to 2,

[0376] with z + x = 3.

[0377] Preferably, R'2 represents a linear or branched alkyl group, preferably linear comprising 1 to 4 carbon atoms, such as ethyl.

[0378] Preferably, R'3 represents a linear or branched alkyl group, preferably linear, comprising 1 to 4 carbon atoms, such as methyl or ethyl.

[0379] Preferably, R' i is an acyclic chain, in particular R' i is a Ci-C6 hydrocarbon chain, linear or branched, saturated or unsaturated, preferably saturated, substituted by one or more thiol groups, preferably substituted by a thiol group.

[0380] Preferably, R\ is a linear saturated Ci-C6 hydrocarbon chain substituted with a thiol group, and R'2 represents an alkyl group comprising 1 to 4 carbon atoms,

[0381] Preferably, R'3 represents an alkyl group comprising 1 to 4 carbon atoms.

[0382] Preferably, z is equal to 3.

[0383] According to a more particular embodiment of the invention, the thiolated alkoxysiloxanes are chosen from those of the following formula (IX):

[0384] (R1O)(R2)(R3)Si-[CH(R4)]t-[N(R'4)-L1]p-SH (IX)

[0385] formula (IX) in which:

[0386] - p is equal to 0 or 1;

[0387] -1 is an integer between 1 and 4, preferably 2;

[0388] - R1 represents a (Ci-C6)alkyl radical;

[0389] - R2 and R3, identical or different, preferably identical, are chosen from a (Ci-C6)alkyl group, in particular Ci-C4, such as methyl, and an (Ci-C6)alkoxy group, in particular (Ci-C4)alkoxy, such as methoxy;

[0390] - R4 and R'4, whether identical or different, represent a hydrogen atom, or a (Ci-C6)alkyl group, such as methyl;

[0391] - L1 represents a linear or branched divalent, saturated hydrocarbon radical in Ci-C20.

[0392] According to a particular embodiment of the invention, the thiolated alkoxysiloxane compounds are chosen from those of the following formula (IX'):

[0393] (R'1O)(R'2)(R'3)Si-CH(R4)-CH(R5)-(L2)q-SH (IX')

[0394] formula (IX') in which:

[0395] - q is equal to 0 or 1;

[0396] - X represents an oxygen or sulfur atom, preferably sulfur;

[0397] - R'1 denotes a (Ci-C6)alkyl radical;

[0398] - R'2 and R'3, identical or different, preferably identical, are chosen from a (Ci-C6)alkoxy group, in particular in Ci-C4, and a (Ci-C6)alkyl radical;

[0399] - R5 represents a hydrogen atom or an alkyl group in Ci-C4 possibly substituted by an amino, thiol or hydroxy group;

[0400] - R4 represents a hydrogen atom or an alkyl group in CrC4, in particular methyl;

[0401] - L2 represents a divalent hydrocarbon group, linear or branched, saturated with Ci-C2O , possibly interrupted by a heteroatom such as -N(H)-, and / or possibly substituted by one or more hydroxy, thiol or amino groups.

[0402] Preferably, the thiolated alkoxysilane(s) are selected from 4-(trimethoxysilyl)-l-butanol, 3-(trimethoxysilyl)-l-propanol, 3-(triethoxysilyl)-l-propanol, 11-(trimethoxysilyl)-l-undecanethiol, 4-(trimethoxysilyl)-2-butanethiol, 2-(triethoxysilyl)-ethanethiol, 3-(triethoxysilyl)-l-propanethiol, 2-(trimethoxysilyl)-ethanethiol, 3-(trimethoxysilyl)-l-propanethiol and 3-(dimethoxymethylsilyl)-1-propanethiol.

[0403] More preferably, the thiolated alkoxysilane(s) are chosen from 2-(triethoxysilyl)-ethanethiol (18236-15-2) and 3-(triethoxysilyl)-l-propanethiol (14814-09-6).

[0404] According to a preferred embodiment of the invention, the (poly)thiol compound(s) are chosen from among the polymeric (poly)thiol compounds.

[0405] Polymeric (poly)thiol compounds can be homopolymers, copolymers, star, comb, brush, and dendritic thiol-resonant polymers. The polymers can be of natural origin, such as polysaccharides and polypeptides, or synthetic, such as acrylics, polyesters, and polyglycols. The thiol motifs can be present as terminal or pendant groups.

[0406] Examples include the polymers described in the following documents: Polymers containing groups of biological activity, CG Overberger et al, Polytechnic Institute of Brooklyn, http: / / pac.iupac.org / publications / pac / pdf / 1962 / pdf / 0402x0521.pdf; EP 1 247 515 A2; US 3,676,440; and EP 1 572 778.

[0407] The polymeric (poly)thiol compounds of the invention are preferably organic and / or silicone-based, more preferably of formula (X):

[0408] POLY(SH)q (X)

[0409] formula (X) in which:

[0410] - q is greater than or equal to 2, preferably greater than or equal to 3;

[0411] - POLY designates a polymeric radical, preferably carbon- or silicon-based; POLY being optionally interrupted by one or more heteroatoms or groups chosen from O, S, N, Si, C(X), and their combinations such as -O-, -OC(X)-, -N(R)-C(X)-, -Si(Rc)(Rd)-O- with R representing a hydrogen atom or a (Ci-C6)alkyl group such as methyl; and / or POLY being optionally substituted by one or more halogen atoms, or a group chosen from Ra(Rb)N- and -(X')aC(X)-(X”)b-Ra; X, X' and X”, identical or different, represent an oxygen atom, a sulfur atom, or an N(Rb) group; a, and b being 0 or 1, preferably the sum of a + b is 1; Ra and Rb, whether identical or different, represent a hydrogen atom, or an (Ci-CiO)alkyl, or aryl(Ci-C4)alkyl group, such as benzyl, preferably Ra and Rb represent a hydrogen atom; and Rc and Rd, whether identical or different, represent an (Ci-CiO)alkyl, aryl(Ci-C4)alkyl or (CrCiO)alkoxy group.

[0412] The methods for preparing the (poly)thiol polymeric compounds implemented according to the invention are known to those skilled in the art; several methods are described below without limitation. The (poly)thiol polymeric compounds implemented according to the invention can be obtained by polymerization, polycondensation of monomer motifs with thiol or protected thiol functions, optionally by co-polymerization or co-polycondensation of monomer motifs lacking thiol functions or protected thiol functions.

[0413] According to one embodiment of the invention, the (poly)thiol polymeric compounds used according to the invention are polymers soluble in cosmetic media, particularly in aqueous or hydroalcoholic media. They are more preferably obtained from amine polymers and their ammonium salts or from polyhydroxylated polymers.

[0414] According to another embodiment of the invention, the thiolated polymers implemented according to the invention are polymers soluble in lipophilic media.

[0415] According to one embodiment of the invention, the polythiol compound is a polymeric compound of formula (X) in which q denotes an integer greater than or equal to 2, and POLY denotes a carbon and / or silicon polymeric radical, preferably silicon, POLY further being able to contain one or more heteroatoms selected from O, N, S and / or one or more functions selected from the (thio)ester, (thio)ketone, (thio)amide, (thio)urea, (thio)carbamate functions, and / or be substituted by one or several (Ci-Cio)alkyl groups, linear or branched, (Ci-Cio)alkoxy groups, linear or branched, it being understood that when POLY is substituted, the thiol functions may be carried by the substituent(s).

[0416] The average molecular weight in molar weight of polythiol polymer compounds, such as those of formula (X), is generally between 500 and 400000 g.mol1, preferably between 500 and 150000 g.mol1.

[0417] According to a particular embodiment of the invention, the polythiol compounds are chosen from polyorganosiloxanes having thiol groups on terminal chains, such as those of formula (XI):

[0418] HS-L4-Si(Ra)(Rb)-O-[Si(Ra)(Rb)-O]n-Si(Ra)(Rb)-L5-SH (XI)

[0419] formula (XI) in which:

[0420] - Ra and Rb, identical or different, preferably identical, represent a group (Ci-C4)alkyl, such as methyl, (Ci-C4)alkoxy, such as methoxy, aryl, such as phenyl, aryloxy, such as phenoxy, aryl(Ci-C4)alkyl, such as benzyl, or aryl(Ci-C4)alkoxy, such as benzoxy, preferably (CrC4)alkyl, such as methyl,

[0421] - n represents an integer greater than or equal to 1, and more particularly the value of n is such that the average molecular weight by weight of silicone is between 500 and 55000 g.mol1; particularly n is an integer between 1 and 100, preferably between 5 and 50, and preferably between 10 and 30, and

[0422] - L4 and L5, identical or different, preferably identical, represent a string hydrocarbon comprising from 1 to 100 carbon atoms, saturated or unsaturated, linear or branched, possibly cyclic, possibly interrupted by one or more heteroatoms, such as oxygen, sulfur or nitrogen, in particular oxygen, in particular represent a covalent bond, a (Ci-C6)alkylene, (Ci-C6)alkylene-oxy, oxy-(Ci-C6)alkylene, (Ci-C6)alkylene-oxy(Ci-C6)alkylene, (Ci-C6)alkylene-oxy(Ci-C6)alkylenoxy or oxy(Ci-C6)alkylene-oxy(Ci-C6)alkylene, preferably a (Cr C6)alkylene, (Ci-C6)alkylene-oxy, oxy-(Ci-C6)alkylene, or (Ci-C6)alkylene-oxy(Ci-C6)alkylene group.

[0423] Preferably, the (poly)thiol compounds are polythiol polyorganosiloxanes, more preferably polythiol polydimethylsiloxanes, in particular chosen from those of formula (XII):

[0424] HS-L4-Si(CH3)2-O-[Si(CH3)2-O]n-Si(CH3)2-L5-SH (XII)

[0425] formula (XII) in which:

[0426] - L4 and L5 are as defined previously in formula (XI), in particular L4 and L5 represent a (Ci-C6)alkylene, (Ci-C6)alkylene-oxy, oxy-(Ci-C6)alkylene, or (Ci-C6)alkylene-oxy(Ci-C6)alkylene group, more preferably a group divalent selected from -R2-, -0-R2-, -R2-0-, -R2-O-R2-, preferably -R2-O-R2-, with R2 representing a linear or branched (C2-C6)alkylene group, preferably linear, such as ethylene or propylene, preferably n-propylene; and

[0427] - n is such as defined in formula (XI).

[0428] As examples of polythiol compounds of formula (XII), we can cite mercaptosiloxane or thiol siloxanes, in which the thiol functions are located at the ends of the chain, marketed by the company SHIN-ETSU under the reference X-22-167B and mercaptosiloxane, in which the mercapto functions are pendant, marketed by the company SHIN-ETSU under the reference KF-2001, or polydimethylsiloxane in which the thiol functions are located at the ends of the chain by thio-n-propyl, 80-120 groups marketed by Gelest under the name DMS - SM 21.

[0429] Preferably, polythiol compounds are polyorganosiloxanes having thiol groups on side chains such as those of formula (XIII):

[0430] Ra-Si(Rb)(Rd)-O-[Si(Ra)(Rb)-O]m-[Si(Rb)(ALK1-SH)-O]n-Si(Rb)(Rd)-Ra (XIII)

[0431] formula (XIII) in which:

[0432] - Ra, and Rb, are such as defined in formula (XI) and Rd is such as defined for Ra and Rb, preferably Ra, Rb, and Rd, which are identical, represent a (Ci-C6)alkyl group, such as methyl;

[0433] - Rd can also represent a (Ci-C6)alkyl group substituted by a (Cr) group C4)alkylamino or amino, or thiol, preferably (Ci-C4)alkyl, such as methyl;

[0434] - ALKi represents a divalent hydrocarbon chain comprising from 1 to 100 carbon atoms, saturated or unsaturated, linear or branched, possibly cyclic, possibly interrupted by one or more heteroatoms such as oxygen, sulfur or nitrogen, especially oxygen, a (thio)carbonyl group C(X) with X representing O, or S, or their combinations such as -O-, -OC(O)- or -C(O)-O-, preferably ALKi represents a (Ci-C6)alkylene group, more preferably (Ci-C4)alkylene, such as propylene;

[0435] - n and m, whether identical or different, represent an integer greater than 2, and more particularly the values ​​of m and n are such that the average molecular weight by weight of said polyorganosiloxane is between 1000 and 55000 g.mol1.

[0436] Examples of polythiol compounds of formula (XIII) include those sold by Genesee Polymers under the names GP-367, GP-71-SS, GP-800 and GP-710s, preferably GP-367, marketed by Genesee Polymers.

[0437] Polythiol compounds include polydimethylsiloxanes comprising at least two thiol groups, such as, for example, products SMS-022, SMS-042 and SMS-992 sold by the company Gelest in https: / / www.gpcsilicones.com / products / silicone-fluids / mercapto-functional, https: / / www.shinetsusilicone-global.com / products / type / oil / detail / search / deg07.shtml, and 1053_Reactive Silicones_Silanes / Silicones -Gelest.

[0438] According to a particular embodiment of the invention, the (poly)thiol compounds are chosen from hyperbranched polymers comprising at least one thiol group and dendrimers bearing at least one thiol group such as thiol PAMAMs.

[0439] Preferably, the (poly)thiol compounds implemented according to the invention are chosen from polydiallylsiloxanes, in particular polydimethylsiloxanes, comprising at least two thiol groups such as those of formula (XIII). C) Polyacrylate compounds

[0440] According to a particular embodiment, the process according to the invention comprises the application of at least one compound (poly)acrylate crosslinking agent.

[0441] By "(poly)acrylate" is meant a compound comprising at least one acrylate ester group H2C=C(Re)-C(0)-Y- with Re representing a hydrogen atom or (Ci-C4)alkyl group, such as methyl, preferably Re representing a hydrogen atom, and Y representing an oxygen atom or an amino group -N(H)-, preferably an oxygen atom.

[0442] More particularly, the (poly)acrylate(s) of the invention have the formula (XIV):

[0443] L[-YC(0)-C(Re)=CH2]q (XIV)

[0444] formula (XIV) in which q and L are such as defined in formula (VIII), Y and Re being such as defined previously, preferably Y = O and Re = H.

[0445] According to a preferred embodiment, the compounds of formula (XIV) are such that L represents a di or trivalent hydrocarbon chain, preferably trivalent, comprising from 1 to 8 carbon atoms, q is 2 or 3, preferably 3, Y represents O, and Re represents a hydrogen atom.

[0446] According to a particular embodiment, the (poly)acrylate compounds are selected from polyorganosiloxanes comprising at least one acrylate group on the side chain such as those of formula (XV):

[0447] Ra-Si(Rb)(Rd)-O-[Si(Ra)(Rb)-O]m-[Si(Rb)(ALKrY-C(O)-C(Re)=CH2)-O]n-Si(Rb)(Rd)-Ra (XV)

[0448] formula (XV) in which:

[0449] - Ra, Rb, and Rd are such as defined in formula (XIII), preferably Ra, Rb, and Rd represent a (Ci-C6)alkyl group, such as methyl,

[0450] - ALKi is such as defined for formula (XIII), preferably ALKi represents a (Ci-C6)alkylene group, more preferably (Ci-C4)alkylene, such as propylene,

[0451] - n and m, whether identical or different, represent an integer greater than 2, and more particularly the values ​​of m and n are such that the average molecular weight by weight of said polyorganosiloxane is between 1000 and 55000 g.mol1,

[0452] - Y is as defined above, preferably is an oxygen atom.

[0453] More particularly, the (poly)acrylate compound may be selected from 1,3-butanedioldiacrylate, 1,4-butanedioldiacrylate, di(trimethylolpropane) tetraacrylate, glycerol 1,3-diglycerol diacrylate, glycerol propoxylate (1PO / OH) triacrylate, 1,6-hexanediol diacrylate, 1,6-hexanediol ethoxylate diacrylate, hydroxypivalyl hydroxypivalate, neopentyl glycol diacrylate, neopentyl glycol propoxylate (1PO / OH) diacrylate, pentaerythritol tetraacrylate, pentaerythritol triacrylate, poly(propylene glycol) diacrylate, tricyclo[5.2.1.02,6]de canedimethanol diacrylate, trimethylolpropane ethoxylate (1EO / OH) methyl ether diacrylate, trimethylolpropane propoxylate triacrylate, trimethylolpropane triacrylate, trimethylolpropane trimethacrylate, tri(propylene glycol) diacrylate, trimethylolpropane triacrylate and tris[2-(acryloyloxy)ethyl] isocyanurate.

[0454] The (poly)acrylate compound can also be selected from N,N'-methylene bis-acrylamide.

[0455] According to this embodiment, the (poly)acrylate compound is associated in its implementation with an amine catalyst as described for example in the articles Progress in coating 129, 21-25 (2019) and Progress in coating 135, 510-516 (2019). Preferably, the amine catalyst(s) are chosen from piperidine, DMAP (Dimethylaminopyridine), DBU (1,8-diazabicyclo[5.4.0]undec-7-ene), DABCO (1,4-diazabicyclo[2.2.2]octane), DBN (1,5-Diazabicyclo[4.3.0]non-5-ene), more preferably chosen from DBU (1,8-diazabicyclo[5.4.0]undec-7-ene), DABCO (1,4-diazabicyclo[2.2.2]octane), DBN (1,5-Diazabicyclo[4.3.0]non-5-ene), and in particular the catalyst is DBU (1,8-Diazabicyclo[5.4.0]undec-7-ene).

[0456] More particularly, (poly)acrylate compounds are chosen from those of formula (XIV), in particular trimethylolpropane triacrylate, and those of formula (XV), more preferably from those of formula (XIV), in particular trimethylolpropane triacrylate. D) Metal alkoxides

[0457] According to a particular embodiment, the process according to the invention comprises the application of at least one crosslinking agent R selected from the following metal alkoxides of formulas (XIVa), (XIVb), (XIVC) and (XIVd), and mixtures thereof: M-(0R1)n (XIVJ RM-(0R1)n.1 (XIVb) (R10)n.1-MR”-M'-(0R1')n • ! (XIVC) RM(R')-(0^), 2 (XXIVd)

[0458] formulas (XIVa), (XIVb), (XIVC) and (XIVd) wherein:

[0459] - M and M', identical or different, represent an atom chosen from among the metals alkaline earth metals, transition metals, lanthanide family metals, post-transition metals such as aluminium or tin and metalloids, such as boron, preferably transition metals, such as Ti, and post-transition metals, such as aluminium;

[0460] - n and n' represent respectively the valences of the atoms represented by M and M';

[0461] - Ri and Rf, identical or different, represent a linear hydrocarbon group or branched, saturated or unsaturated, having from 1 to 30 carbon atoms, preferably from 1 to 6 carbon atoms, said hydrocarbon group being optionally interrupted by 1 to 20 heteroatoms selected from O, N, S and P, in particular O or N, and / or said hydrocarbon group being optionally substituted by one or more hydroxy or carbonyl groups; - R and R', identical or different, represent a hydrogen atom or a hydrocarbon group, linear, branched, acyclic or cyclic, saturated or unsaturated, having from 1 to 30 carbon atoms, preferably from 2 to 20 carbon atoms, possibly interrupted by 1 to 20 heteroatoms chosen from O, N, S and / or P, in particular O or N and / or said hydrocarbon group possibly being substituted by one or more hydroxy or carbonyl groups;

[0462] - R” represents -O-, -N(R2)-, -S- or a linear, hydrocarbon divalent group, cyclic or branched, saturated or unsaturated, having from 1 to 30 carbon atoms, preferably from 2 to 20 carbon atoms, optionally interrupted by 1 to 20 heteroatoms chosen from O, N, S and P, especially O or N, with R2 representing a hydrocarbon group, linear, cyclic or branched, saturated or unsaturated, having from 1 to 30 carbon atoms, preferably from 2 to 20 carbon atoms.

[0463] Preferably, M and M', identical or different, represent an atom chosen from among the transition metals, such as titanium, or zirconium or the alkaline earth metals such as magnesium, more preferably chosen from among the transition metals, such as titanium or zirconium, even more preferably titanium.

[0464] Preferably, the organometallic compound(s) are chosen from alkoxides of formula (XIVa) as defined above. According to this preferred embodiment, the organometallic compound(s) are more particularly chosen from alkoxides of formula (XIVa), in which M represents an atom chosen from transition metals, lanthanide metals, post-transition metals such as aluminum and tin, and metalloids such as boron. or alkaline earth metals such as magnesium or calcium; n represents the valence of the atom represented by M; Ri represents a saturated, linear or branched hydrocarbon group having from 1 to 30 carbon atoms, preferably from 1 to 6 carbon atoms.

[0465] According to another more preferred embodiment, the organometallic compound(s) are selected from alkoxides of formula (XIVa), in which M represents an atom selected from transition metals, such as zirconium or titanium, lanthanide metals, post-transition metals, such as aluminum, tin, metalloids, such as boron, and alkaline earth metals, such as magnesium, preferably M represents a titanium atom; n represents the valence of the atom represented by M, in particular 1, 2, 3 or 4, in particular 4; Ri represents a methyl, ethyl, 2-ethylhexyl, propyl, isopropyl, n-butyl, isobutyl or t-butyl group.

[0466] According to a further preferred embodiment, the organometallic compound(s) are selected from zirconium ethoxide (Zr(OC2H5)4), zirconium propoxide (Zr(OCH2CH2CH3)4), zirconium isopropoxide (Zr(OCH(CH3)2)4), zirconium butoxide (Zr(OCH2CH2CH2CH3)4), zirconium tert-butoxide (Zr(OC(CH3)3)4), titanium ethoxide (Ti(OC2H5)4), titanium propoxide (Ti(OCH2CH2CH3)4), titanium isopropoxide (Ti(OCH(CH3)2)4), titanium butoxide (Ti(OCH2CH2CH2CH3)4), titanium tert-butoxide (Ti(OC(CH3)3)4), 2-ethylhexyloxide titanium (Ti(OCH2CH(C2H5)(CH2)3CH3)4), and mixtures thereof, more preferably chosen from zirconium propoxide, titanium propoxide, titanium butoxide and mixtures thereof.

[0467] More preferably, the crosslinking agent R is a compound of formula (XXIVa), preferably in which M represents an atom selected from among the transition metals, in particular titanium, such as titanium butoxide. E) Polycarbonyl compounds

[0468] According to a particular embodiment, the process according to the invention comprises the application of at least one crosslinking agent R composed of (poly)carbonyl.

[0469] In particular, the (poly)carbonyl compound is selected from terephthalaldehyde, 5,5-dimethyl-1,3-cyclohexanedione, phenylglyoxal, isophthalaldehyde, 4-acetylbenzaldehyde, 4,4-diformyltriphenylamine, 2-acetylbenzaldehyde, 3-(2-furoyl)quinoline-2-carboxaldehyde, 3-(2-furoyl)quinoline-2-carboxaldehyde, 3-acetylbenzaldehyde, 9-(2-ethylhexyl)carbazole-3,6-dicarboxaldehyde, phthaldialdehyde, 1,3-cyclohexanedione, 4,4'-biphenyldicarboxaldehyde, benzene-1,3,5-tricarboxaldehyde, and nonionic or anionic oxidized polysaccharides such as oxidized inulins, particularly those of formula (II) such as defined below. In particular, (poly)carbonyl compounds comprise a C5-C7 carbocycle, saturated or unsaturated, aromatic, preferably aromatic, such as phenyl, or non-aromatic and saturated such as cyclohexyl, more preferably unsaturated and aromatic, such as terephthalaldehyde.

[0470] According to a particular embodiment, the (poly)carbonyl compound(s) are chosen from non-ionic or anionic oxidized polysaccharides comprising one or more aldehyde groups, and optionally one or more anionic groups.

[0471] These anionic groups are preferably carboxy or carboxylate groups.

[0472] The non-ionic or anionic oxidized polysaccharides according to the invention can be represented by the following formula (II):

[0473] P-(CHO)m (COOQ)n (II)

[0474] formula (II) in which:

[0475] - P represents a polysaccharide chain, preferably made up of monosaccharides comprising 5 or more carbon atoms, preferably 6 or more than 6 carbon atoms, and more particularly 6 carbon atoms;

[0476] - Q is chosen from a hydrogen atom, ions from an alkali metal or alkaline earths, such as sodium, potassium, ammonia, organic amines, such as monoethanolamine, diethanolamine, triethanolamine and 3-aminopropanediol-1,2 or 2-amino-1,3-propanediol and basic amino acids, such as lysine, arginine, sarcosine, ornithine, citrulline;

[0477] - m + n is greater than or equal to 1;

[0478] - m is such that the degree of substitution of the polysaccharide by one or more aldehyde groups (DS(CHO)), is in the range from 0.001 to 2, preferably from 0.005 to 1.5;

[0479] - n is such that the degree of substitution of the polysaccharide by one or more carboxylic groups (DS(COOX)), is in the range from 0 to 2, preferably from 0.001 to 1.5.

[0480] By degree of substitution DS(CHO) or DS(COOX) of the polysaccharides according to the invention, we mean the ratio between the number of carbons oxidized to an aldehyde or carboxylic group for all repeating units and the number of elementary monosaccharides (even those opened by pre-oxidation) constituting the polysaccharide. The CHO and COOX groups can be obtained during the oxidation of certain carbon atoms, for example on carbon atoms 2, 3, or 6, of a 6-carbon saccharide unit.

[0481] Preferably, the oxidation can take place in carbon 2 and 3, more particularly from 0.01% to 75% by number, and preferably from 0.1% to 50% by number of the rings that may have been opened.

[0482] The polysaccharide chain, represented by P, is preferably selected from celluloses, starches, maltodextrins, guar gums, xanthan gums, pullulan gums, agar-agar gums, carrageenan gums, gellan gums, gum arabic, polyxylans and tragacanth gums and their derivatives.

[0483] By derivative, we mean the compounds obtained by chemical modification of the aforementioned compounds. These may be esters, amides, or ethers of said compounds.

[0484] Oxidation can be carried out according to a process known in the art, for example according to the process described in FR 2 842 200, in document FR 2 854 161 or in the article “Hydrophobic films from maize bran hemicelluloses” by E. Fredon et al, Carbohydrate Polymers 49, pages 1 to 12 (2002).

[0485] Another oxidation process is described in the article “Water soluble oxidized starches by peroxide reaction extrusion” Industril Crops and Products 7, RE Wing, JL Willet 45-52 (1997).

[0486] According to this embodiment, the (poly)carbonyl compound is associated in its implementation with an amine catalyst, as described in the articles Progress in coating 129, 21-25 (2019) and Progress in coating 135, 510-516 (2019). Preferably, the amine catalyst(s) are chosen from piperidine, DMAP (Dimethylaminopyridine), DBU (1,8-diazabicyclo[5.4.0]undec-7-ene), DABCO (1,4-diazabicyclo[2.2.2]octane), DBN (1,5-Diazabicyclo[4.3.0]non-5-ene), more preferably chosen from DBU (1,8-diazabicyclo[5.4.0]undec-7-ene), DABCO (1,4-diazabicyclo[2.2.2]octane), DBN (1,5-Diazabicyclo[4.3.0]non-5-ene), and in particular the catalyst is DBU (1,8-Diazabicyclo[5.4.0]undec-7-ene).

[0487] According to a preferred embodiment, the crosslinking agent(s) are selected from A) (poly)amine compounds, B) (poly)thiol compounds, C) (poly)acrylate compounds, D) metal alkoxides, and E) (poly)carbonyl compounds, and preferably from polyamine, polythiol, polycarbonyl, polyacrylate, metal alkoxide, amino alkoxysilane compounds comprising only one primary and / or secondary amine group, and mixtures thereof, optionally in association with an amine catalyst, in particular selected from piperidine, DMAP (dimethylaminopyridine), DBU (1,8-diazabicyclo[5.4.0]undec-7-ene), DABCO (1,4-diazabicyclo[2.2.2]octane), DBN (1,5-diazabicyclo[4.3.0]non-5-ene), more preferably selected from DBU (l,8-diazabicyclo[5.4.0]undec-7-ene), DABCO (l,4-diazabicyclo[2.2.2]octane), DBN (l,5-Diazabicyclo[4.3.0]non-5-ene), and in particular the catalyst is DBU (l,8-Diazabicyclo[5.4.0]undec-7-ene); more preferably at least one crosslinking agent is chosen from spermidine, titanium butoxide (Ti(OCH2CH2CH2CH3)4), trimethylolpropane triacrylate, terephthalaldehyde, (3-aminopropyl)triethoxysilane (APTES), polydimethylsiloxanes including . primary amine groups at the end of the chain or on side chains, such as Bis-Cetearyl Amodimethicone, 4,7,10-trioxa-l,13-tridecanediamine, polydimethylsiloxanes containing at least two thiol groups, triamine polyethers, in particular polyetheramines (or jeffamine), chitosans (notably poly(D-glucosamine)), and mixtures thereof.

[0488] According to one embodiment, the crosslinking agent(s) are chosen from A) (poly)amine compounds, in particular from alkoxysilanes comprising only one primary and / or secondary amine group, such as APTES, B) (poly)thiol compounds.

[0489] In particular, said (poly)amine compounds A) are selected from a) chitosans, such as poly(D-Glucosamine), b) diamine polyethers, particularly polyethylene glycol α,co-diamine (with an amine function at the chain end), c) triamine polyethers, such as Polyetheramine (or jeffamine), d) aminoalkoxysilanes, such as APTES, and e) polydialkylsiloxanes comprising primary amine groups at the chain end or on side chains, particularly polydimethylsiloxanes comprising primary amine groups, such as bis(3-aminopropyl)-terminated poly(dimethoxysiloxane) (PDMS-diNH2) and amodimethicones comprising amine groups on side chains such as Bis-Cetearyl amodimethicone, particularly that marketed by Momentive Performance Materials, f) NH2-alk-NH2 polyamine compounds, in which alk denotes a C2-C20 divalent hydrocarbon chain,possibly interrupted by one or more heteroatoms chosen from -O-, -N(R)- with R denoting a hydrogen atom or a Ci-C4 alkyl radical, such as spermidine.

[0490] According to a preferred embodiment, said (poly)amine compounds A) are selected from a) chitosans, such as poly(D-Glucosamine), c) triamine polyethers, such as Polyetheramine (or jeffamine), and e) polydialkylsiloxanes comprising primary amine groups at the end of the chain or on side chains, particularly polydimethylsiloxanes comprising primary amine groups, such as bis(3-aminopropyl)-terminated poly(dimethoxysiloxane) (PDMS-diNH2) and amodimethicones comprising amine groups on side chains such as bis-cetearyl amodimethicone, in particular that marketed by Momentive Performance Materials, and f) NH2-alk-NH2 polyamine compounds, in which alk denotes a C2-C20 hydrocarbon divalent chain optionally interrupted by one or more heteroatoms chosen from -O-, -N(R)- with R denoting a hydrogen atom or a Ci-C4 alkyl radical, such as spermidine or 4,7,10-Trioxa-1,13-tridecanediamine. ,

[0491] In particular, said (poly)thiol compounds B) are selected from a) polydialkylsiloxanes with thiol functions, and b) alkoxysilanes with thiol functions, particularly are chosen from a) polydialkylsiloxanes with thiol functions, preferably polydimethylsiloxanes comprising thiol groups on the side chain (such as mercaptopropyl) especially those of formula (XIII).

[0492] In particular, said (poly)acrylate C) compounds are selected from those of formula (XIV) in particular trimethylolpropane triacrylate, and those of formula (XV) in particular copolymers of dimethylsiloxane and acryloxypropyl)methylsiloxane, preferably trimethylolpropane triacrylate.

[0493] According to a preferred embodiment, the crosslinking agent(s) ii) is / are selected from:

[0494] A) (poly)amine compounds selected from:

[0495] ia) chitosans such as poly(D-Glucosamine),

[0496] ib) diamine polyethers, in particular polyethylene glycol a, co-diamine, with an amine function at the end of the chain,

[0497] ic) triamine polyethers, in particular polyetheramine (or jeffamine),

[0498] id) aminoalkoxysilanes, in particular APTES,

[0499] e) NH2-alk-NH2 polyamine compounds, in which alk denotes a C2-C20 hydrocarbon divalent chain, optionally interrupted by one or more heteroatoms selected 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

[0500] if) polydialkylsiloxanes comprising primary amine groups at the end of the chain or on side chains, in particular polydimethylsiloxanes comprising primary amine groups, more particularly poly(dimethoxysiloxane) terminated by bis(3-aminopropyl) (PDMS-diNH2) and amodimethicones comprising amine groups on side chains, more particularly bis-cetearyl amodimethicone;

[0501] B) (poly)thiol compounds selected from:

[0502] iia) thiol-functionalized polydialkylsiloxanes, and

[0503] iib) alkoxysilanes with thiol functions,

[0504] and in particular selected from compounds iia) polydialkylsiloxanes with thiol functions, preferably from polydimethylsiloxanes comprising thiol groups on the side chain, in particular mercaptopropyl, and more particularly selected from compounds of formula (XIII):

[0505] Ra-Si(Rb)(Rd)-O-[Si(Ra)(Rb)-O]m-[Si(Rb)(ALK1-SH)-O]n-Si(Rb)(Rd)-Ra (XIII)

[0506] formula (XIII) in which:

[0507] - Ra and Rb, identical or different, preferably identical, represent a group (Ci-C4)alkyl, in particular methyl, a (Ci-C4)alkoxy group, in particular methoxy, an aryl group, in particular phenyl, an aryloxy group, in particular phenoxy, an aryl(Ci-C4)alkyl group, in particular benzyl, or an aryl(Ci-C4)alkoxy group, in particular benzoxy, and preferably a (Ci-C4)alkyl group, more preferably methyl,

[0508] - Rd represents a (CrC4)alkyl group, in particular methyl, a (CrC4 )alkoxy, in particular methoxy, an aryl group, in particular phenyl, an aryloxy group, in particular phenoxy, an aryl(Ci-C4)alkyl group, in particular benzyl, an aryl(Ci-C4)alkoxy group, in particular benzoxy, or a (Ci-C6)alkyl group substituted by a (Ci-C4)alkylamino, amino, or thiol group, and preferably a (CrC4)alkyl group, more preferably methyl,

[0509] and preferably Ra, Rb, and Rd, are identical and represent a (Ci-C6)alkyl group, more preferably methyl,

[0510] - ALKi represents a divalent hydrocarbon chain comprising from 1 to 100 carbon atoms, saturated or unsaturated, linear or branched, possibly cyclic, possibly interrupted by one or more heteroatoms, such as oxygen, sulfur or nitrogen, in particular oxygen, a (thio)carbonyl group C(X) with X representing O or S, or their combinations, in particular -O-, -OC(O)- or -C(O)-O-, preferably ALKi represents a (Ci-C6)alkylene group, more preferably (CrC4)alkylene, even more preferably propylene,

[0511] - n and m, whether identical or different, represent an integer greater than 2, and in in particular the values ​​of m and n are such that the average molecular weight by weight of said polyorganosiloxane is between 1000 and 55000 g.mol1; and

[0512] C) (poly)acrylate compounds of formula (XIV):

[0513] L[-YC(O)-C(Re)=CH2]q (XIV)

[0514] formula (XIV) in which:

[0515] - q represents an integer greater than or equal to 2, in particular n is between inclusively between 2 and 10, and preferably between 2 and 5,

[0516] - L denotes a multivalent group that is at least divalent, in particular comprising between 1 and 500 carbon and / or silicon atoms, more particularly between 2 and 40 carbon and / or silicon atoms, even more particularly between 3 and 30 carbon and / or silicon atoms, preferably between 6 and 20 carbon atoms, linear or branched, saturated or unsaturated, or (hetero)cyclic, saturated or unsaturated; L being optionally interrupted and / or terminated by one or more heteroatoms or groups selected from O, S, N, Si, C(X), and their combinations, in particular -O-, -OC(X)-, -N(R)-C(X)-, -Si(Rc)(Rd)-O- with R representing a hydrogen atom or a (Ci-C6)alkyl group, in particular methyl; and / or L possibly being substituted by one or more groups chosen from: -N(Ra)Rb, and -(X')aC(X)-(X”)b-Ra, with X, X' and X”, identical or different, representing an oxygen atom, a sulfur atom, or an N(Rb) group, a and b being 0 or 1, preferably the sum of a and b being 1, Ra and Rb, identical or different, representing a hydrogen atom, a (Ci-C6)alkyl group, or an aryl(Ci-C4)alkyl group, in particular benzyl, preferably Ra and Rb represent a hydrogen atom, and Rc and Rd, identical or different, represent a (Ci-C6)alkyl, aryl(Ci-C4)alkyl or (Ci-C6)alkoxy group,

[0517] - Re represents a hydrogen atom or an (CrC4)alkyl group, in particular methyl, preferably Re, represents a hydrogen atom, and

[0518] - Y represents an oxygen atom or an amino group -N(H)-, preferably a oxygen atom,

[0519] preferably Y is an oxygen atom and Re is a hydrogen atom, preferably L represents a di- or trivalent hydrocarbon chain, preferably trivalent, comprising from 1 to 8 carbon atoms, q is 2 or 3, preferably 3, and

[0520] more preferably the compounds of formula (XIV) are trimethylolpropane triacrylate;

[0521] D) metal alkoxides selected from: zirconium ethoxide (Zr(OC2H5)4), zirconium propoxide (Zr(OCH2CH2CH3)4), zirconium isopropoxide (Zr(OCH(CH3)2)4), zirconium butoxide (Zr(OCH2CH2CH2CH3)4), zirconium tert-butoxide (Zr(OC(CH3)3)4), titanium ethoxide (Ti(OC2H5)4), titanium propoxide (Ti(OCH2CH2CH3)4), titanium isopropoxide (Ti(OCH(CH3)2)4), titanium butoxide (Ti(OCH2CH2CH2CH3)4), titanium tert-butoxide (Ti(OC(CH3)3)4), 2-ethylhexyl titanium (Ti(OCH2CH(C2H5)(CH2)3CH3)4), and mixtures thereof, more preferably chosen from zirconium propoxide, titanium propoxide, titanium butoxide and mixtures thereof,

[0522] E) (poly)carbonyl compounds selected from (poly)carbonyl compounds comprising a C5-C7 carbocycle, saturated or unsaturated, aromatic, preferably aromatic, such as phenyl, or non-aromatic and saturated such as cyclohexyl, more preferably unsaturated and aromatic, such as terephthalaldehyde.

[0523] COSMETIC ACTIVES iv)

[0524] According to a particular embodiment, the process of the invention further comprises the application of iv) at least one cosmetic active ingredient, on said keratinous materials.

[0525] More particularly, in the treatment process according to the invention, at least one of the compositions "Cl", "C2", "C3", "C4" or "C5" implemented comprises one or more cosmetic active ingredients.

[0526] In particular, the cosmetic active ingredient(s) iv) is / are chosen from:

[0527] a) coloring materials (or coloring agents), in particular selected from pigments, direct colorants and mixtures thereof,

[0528] b) active ingredients for the care of keratinous materials, preferably of the skin,

[0529] c) UV filters, and

[0530] d) their mixtures.

[0531] According to a particular embodiment, at least one cosmetic active ingredient is chosen from coloring materials, preferably chosen from pigments, direct colorants and their mixtures, more preferably pigments.

[0532] According to another embodiment, at least one of the compositions “Cl”, “C2”, “C3”, “C4” or “C5” implemented comprises one or more cosmetic actives chosen from a) colouring materials (or colouring agents), in particular chosen from pigments, direct colorants and their mixtures, preferably chosen from pigments.

[0533] According to a particular embodiment, the composition “Cl” contains at least one cosmetic active ingredient iv) as defined above and below, preferably chosen from a) colouring materials, and more preferably chosen from pigments.

[0534] According to a particular embodiment, composition “C2” contains at least one cosmetic active ingredient iv) as defined above and below, preferably chosen from a) colouring materials, and more preferably chosen from pigments.

[0535] According to a particular embodiment, the composition “C3” contains at least one cosmetic active ingredient iv) as defined above and below, preferably chosen from a) colouring materials, and more preferably chosen from pigments.

[0536] Of course, a person skilled in the art will take care to choose this or these possible cosmetic active ingredients, and / or their quantity, in such a way that the advantageous properties of the corresponding composition according to the invention are not, or substantially not, altered by the envisaged addition.

[0537] COLORING MATERIALS

[0538] According to a particular embodiment, the process of the invention uses one or more coloring materials.

[0539] More particularly, in the process of the invention, at least one of the compositions "Cl", "C2", "C3", "C4" or "C5" implemented, comprises at least one coloring matter, particulate or not, water-soluble or not, and preferably at a rate of at least 0.01% by weight, relative to the total weight of the composition considered.

[0540] For obvious reasons, this quantity is likely to vary significantly with regard to the intensity of the color effect sought and the colonic intensity provided by the coloring materials considered and its adjustment clearly falls within the competence of the person skilled in the art.

[0541] Preferably, at least one of the compositions "Cl", "C2", "C3", "C4" or "C5" comprises at least one colouring material selected from pigments, direct dyes and their mixtures, more preferably pigments.

[0542] More preferably, the pigment(s) of the invention are chosen from carbon black, iron oxides, in particular yellow, red and black and iron oxide coated micas, triarylmethane pigments, in particular blue and violet, in particular BLUE 1 LAKE, azo pigments, in particular red, more particularly D&C RED 7, the alkali metal salt of lithol red, in particular the calcium salt of lithol red B, and even more preferably from red iron oxides, yellow iron oxides and azo pigments, in particular red, more particularly D&C RED 7.

[0543] PIGMENTS

[0544] For the purposes of this invention, "pigment" means any compound capable of imparting color to keratinous materials. These compounds have a solubility in water at 25 °C and atmospheric pressure (760 mmHg) of less than 0.05% by weight, and preferably less than 0.01% by weight.

[0545] Suitable pigments for the invention may include, in particular, organic and / or mineral pigments known in the art, especially those described in Kirk-Othmer's Encyclopedia of Chemical Technology and Ullmann's Encyclopedia of Industrial Chemistry.

[0546] These pigments can be synthetic or natural.

[0547] These pigments can be in the form of powder or pigment paste.

[0548] They may be coated or uncoated.

[0549] These pigments can, for example, be chosen from mineral pigments, organic pigments, lacquers, special effect pigments such as mother-of-pearl or glitter, and mixtures thereof.

[0550] A pigment suitable for the invention can be chosen from among mineral pigments.

[0551] By "mineral pigment" is meant any pigment that meets the definition of Ullmann's encyclopedia in the chapter on inorganic pigments. Among the mineral pigments useful in the present invention, we can cite manganese violet, ultramarine blue, chromium hydrate, ferric blue, and oxides or dioxides of titanium, zirconium, or cerium, as well as oxides of zinc, iron, or chromium.

[0552] It may also be a pigment having a structure that is, for example, of the sericite / brown iron oxide / titanium dioxide / silica type. Such a pigment is marketed, for example, under the reference Coverleaf NS or JS by Chemicals And Catalysts and has a contrast ratio close to 30. It may also be a pigment having a structure that is, for example, of the silica microspheres containing iron oxide type. An example of a pigment with this structure is that marketed by Miyoshi under the reference PC Bail PC-LL-100 P, this pigment being composed of silica microspheres containing yellow iron oxide.

[0553] Advantageously, the pigments may be iron oxides and / or titanium dioxides.

[0554] A pigment suitable for the invention can be chosen from among organic pigments.

[0555] By "organic pigment" is meant any pigment that meets the definition in the Ullmann Encyclopedia in the chapter on organic pigments. Examples of organic pigments useful in the present invention include nitroso, nitro, azo, xanthene, pyrene, quinoline, quinoline, anthraquinone, triphenylmethane, fluorane, phthalocyanine, metal complex type, isoindolinone, isoindoline, quinacridone, perinone, perylene, diketopyrrolopyrrole, indigo, thioindigo, dioxazine, triphenylmethane, and quinophthalone.In particular, white or colored organic pigments may be chosen from carmine, carbon black, aniline black, azo yellow, quinacridone, phthalocyanine blue, blue pigments coded in the Color Index under references CI 42090, 69800, 69825, 74100, 74160, yellow pigments coded in the Color Index under references CI 11680, 11710, 19140, 20040, 21100, 21108, 47000, 47005, green pigments coded in the Color Index under references CI 61565, 61570, 74260, orange pigments coded in the Color Index under reference CI 11725, 45370, 71105, the red pigments coded in the Color Index under the references CI 12085, 12120, 12370, 12420, 12490, 14700, 15525, 15580, 15620, 15630, 15800, 15850, 15865, 15880, 26100, 45380, 45410, 58000, 73360, 73915, 75470, the pigments obtained by oxidative polymerization of indole, phenolic derivatives as described in patent FR 2 679 771. .

[0556] By way of example, we can also cite organic pigment pastes such as the products sold by the company HOECHST under the name: COSMENYL YELLOW IOG: Pigment YELLOW 3 (CI 11710); COSMENYL YELLOW G: Pigment YELLOW 1 (CI 11680); COSMENYL ORANGE GR: Pigment ORANGE 43 (CI 71105); COSMENYL RED R: Pigment RED 4 (CI 12085); COSMENYL CARMINE FB: Pigment RED 5 (CI 12490); COSMENYL VIOLET RL: Pigment VIOLET 23 (CI 51319); COSMENYL BLUE A2R: Pigment BLUE 15.1 (CI 74160); COSMENYL GREEN GG: Pigment GREEN 7 (CI 74260); COSMENYL BLACK R: Pigment BLACK 7 (CI 77266).

[0557] The pigments according to the invention can also be in the form of composite pigments as described in patent EP 1 184 426. These composite pigments can be composed in particular of particles comprising an inorganic core, at least one binder ensuring the fixation of organic pigments on the core, and at least one organic pigment covering at least partially the core.

[0558] The organic pigment can also be a lacquer.

[0559] By "lacquer" is meant dyes adsorbed onto insoluble particles, the whole thus obtained remaining insoluble during use.

[0560] Examples of inorganic substrates on which dyes are adsorbed include alumina, silica, calcium sodium borosilicate or calcium aluminum borosilicate, and aluminum. Carminic acid is one example of a dye adsorbed onto organic substrates. Other colorants known by the following names include: D&C Red 21 (CI 45380), D&C Orange 5 (CI 45370), D&C Red 27 (CI 45410), D&C Orange 10 (CI 45425), D&C Red 3 (CI 45430), D&C Red 4 (CI 15510), D&C Red 33 (CI 17200), D&C Yellow 5 (CI 19140), D&C Yellow 6 (CI 15985), D&C Green (CI 61570), D&C Yellow 10 (CI 77002), D&C Green 3 (CI 42053), D&C Blue 1 (CI 42090), FDC Red 4, D&C Red 6, D&C Red 22, D&C Red 28, D&C Red 30, D&C Orange 4, D&C Yellow 8, D&C Green 5, D&C Red 17, D&C Green 6, D&C Yellow 11, D&C Violet 2, Sudan red, carotenes (beta-carotene, lycopene),Xanthophylls (capsanthin, capsorubin, lutein), palm oil, Sudan brown, quinoline yellow, annatto, curcumin, betanin (beetroot), carmine, copper chlorophyllin, methylene blue, anthocyanins (enocianin, black carrot, hibiscus, elderberry), caramel, riboflavin, beetroot juice, and caramel.

[0561] As examples of lacquers, we can cite the product known under the following name: D & C Red 7 (CI 15 850 :1).

[0562] The pigment can also be a special effects pigment.

[0563] By "special effect pigments" is meant pigments which generally create a colored appearance (characterized by a certain shade, a certain vibrancy and a certain clarity) that is non-uniform and changes depending on the viewing conditions (light, temperature, viewing angles, etc.). They are thus distinguished from colored pigments which provide a uniform opaque, semi-transparent or conventional transparent tint.

[0564] There are several types of special effect pigments, those with a low refractive index such as fluorescent or photochromic pigments, and those with a higher refractive index such as mother-of-pearl, interference pigments or glitter.

[0565] The size of the pigment used in the composition according to the present invention is generally between 10 nm and 200 µm, preferably between 20 nm and 80 µm, and more preferably between 30 nm and 50 µm.

[0566] The pigments can be dispersed within the composition by means of a dispersing agent.

[0567] This dispersing agent may be a surfactant, an oligomer, a polymer, or a mixture of several of these, possessing one or more functionalities having a strong affinity for the surface of the particles to be dispersed. In particular, they may adhere physically or chemically to the surface of the pigments. These dispersants exhibit, In addition, at least one functional group compatible with or soluble in the continuous medium is required. In particular, esters of 12-hydroxystearic acid, and of C8 to C2o fatty acids and polyols such as glycerol and diglycerin are used, such as poly(12-hydroxystearic acid) stearate with a molecular weight of approximately 750 g / mol, such as that sold under the name Solsperse 21 000 by Avecia, polyglyceryl-2 dipolyhydroxystearate (CTFA) sold under the reference Dehymyls PGPH by Henkel, or polyhydroxystearic acid such as that sold under the reference Arlacel P100 by Uniqema, and mixtures thereof.Other dispersants usable in the compositions of the invention include quaternary ammonium derivatives of polycondensed fatty acids such as Solsperse 17000 sold by Avecia, and polydimethylsiloxane / oxypropylene mixtures such as those sold by Dow Corning under the references DC2-5185 and DC2-5225 C. The pigments used in the composition may be surface-treated with an organic agent. In one particular embodiment, the dispersing agent(s) are amino-silicone type, different from the alkoxysilanes described above, and are cationic. Preferably, the pigment(s) is / are selected from mineral, mixed mineral-organic, or organic pigments.

[0568] According to a particular embodiment, the pigment(s) according to the invention are organic pigments, preferably organic pigments treated on the surface by an organic agent chosen from silicone compounds.

[0569] According to another embodiment of the invention, the pigment(s) according to the invention are mineral pigments.

[0570] DIRECT COLORANTS

[0571] According to a particular embodiment, the process according to the invention comprises the application of one or more direct dye(s). By "direct dye," we mean natural and / or synthetic dyes, other than oxidation dyes. These are dyes that diffuse superficially onto the fiber. They may be ionic or non-ionic, preferably cationic or non-ionic.

[0572] Among the direct dyes suitable for the invention, mention may be made of azo direct dyes; (poly)methine dyes such as cyanines, hemicyanines and styryls; carbonyl dyes; azine dyes; nitro(hetero)aryl dyes; tri(hetero)arylmethane dyes; porphyrin dyes; phthalocyanine dyes and natural direct dyes, alone or in the form of mixtures.

[0573] Direct dyes are preferably cationic direct dyes. Examples include hydrazono cationic dyes of formulas (A) and (B) below and azo cationic dyes of formulas (C) and (D) below:

[0574] Hét+-C(Ra)=NN(Rb)-Ar, Q (A)

[0575] Hét+-N(Ra)-N=C(Rb)-Ar, Q (B)

[0576] Het+-N=N-Ar, Q (C)

[0577] Ar+-N=N-Ar' ', Q (D)

[0578] formulas (A) to (D) in which:

[0579] - Het+ represents a cationic heteroaryl radical, preferentially charged endocyclic cationic such as imidazolium, indolium, or pyridinium, possibly preferentially substituted by at least one (CrC8)alkyl group such as methyl;

[0580] - Ar+ represents an aryl radical, such as phenyl or naphthyl, with a cationic charge exocyclic preferentially ammonium particularly tri(Ci-C8)alkyl-ammonium such as trimethylammonium;

[0581] - Ar represents an aryl group, in particular phenyl, possibly substituted, preferably by one or more electron-donating groups such as (CrC8)alkyl possibly substituted, (CrC8)alkoxy possibly substituted, (di)(Ci-C8)(alkyl)amino possibly substituted on the alkyl group(s) by a hydroxy group, aryl(Ci-C8)alkylamino, and N-(Ci-C8)alkyl-N-aryl(Ci-C8)alkylamino possibly substituted or else Ar represents a julolidine group;

[0582] - Ar” represents a (hetero)aryl group possibly substituted such that phenyl or pyrazolyl possibly substituted, preferably by one or more (Ci-C8)alkyl, hydroxy, (di)(Ci-C8)(alkyl)amino, (Ci-C8)alkoxy or phenyl groups;

[0583] - Ra and Rb, identical or different, representing a hydrogen atom or a (CrC8)alkyl group possibly substituted, preferably by a hydroxy group;

[0584] or the substituent Ra with a substituent of Het+ and / or Rb with a substituent of Ar together form with the atoms which bear them a (hetero)cycloalkyl; particularly Ra and Rb, representing a hydrogen atom or a (Cr C4)alkyl group possibly substituted by a hydroxy group;

[0585] - Q' represents an organic or mineral anionic counterion such as a halide or an alkyl sulfate.

[0586] In particular, one can cite the endocyclic cationic azo and hydrazono direct dyes of formula (A) to (D) as defined above.

[0587] More specifically, endocyclic cationic direct dyes described in patent applications WO 95 / 15144, WO 95 / 01772 and EP-714954.

[0588] Preferably, the direct dyes are chosen from the compounds with the following formulas (E) and (F):

[0589] [Chem.2]

[0590] (E)

[0591] [Chem.3]

[0592] (F)

[0593] formula (E) or (F) wherein:

[0594] - R1 represents an (Ci-C4)alkyl group such as methyl;

[0595] - R2 and R3, whether identical or different, represent a hydrogen atom or a (Ci-C4)alkyl group such as methyl;

[0596] - R4 represents a hydrogen atom or an electron-donating group such as (Ci -C8)alkyl possibly substituted, (Ci-C8)alkoxy possibly substituted, (di)(Ci-C8)(alkyl)amino possibly substituted on the alkyl group(s) by a hydroxy group; particularly R4 is a hydrogen atom;

[0597] - Z represents a CH group or a nitrogen atom, preferably CH;

[0598] - Q" is an anionic counter ion as defined above, particularly halide such as chloride or an alkyl sulfate such as methyl sulfate or mesytyl.

[0599] In particular, the dyes of formula (E) and (F) are selected from Basic Red 51, Basic Yellow 87, and Basic Orange 31, or their derivatives, with Q being an anionic counterion as defined above, particularly a halide such as chloride or an alkyl sulfate such as methyl sulfate or mesytyl. The direct dyes may be selected from anionic direct dyes. The anionic direct dyes of the invention are dyes commonly referred to as "acid" direct dyes because of their affinity for alkaline substances.

[0600] By "anionic direct dyes" is meant any direct dye comprising in its structure at least one CO2R' or SO3R' substituent with R' designating a hydrogen atom or a cation from a metal or an amine, or an ammonium ion.

[0601] Anionic direct dyes may be selected from acidic nitro direct dyes, acidic azo dyes, acidic azinic dyes, acidic triarylmethanic dyes, acidic indoamine dyes, acidic anthraquinone dyes, indigoids and acidic natural dyes.

[0602] Among the natural direct dyes that can be used according to the invention are lawsone, juglone, alizarin, purpurin, carminic acid, kermesic acid, purpurogallin, protocatechaldehyde, indigo, isatin, curcumin, spinulosin, apigenidine, and orceins. Extracts or decoctions containing these natural dyes, and in particular henna-based poultices or extracts, can also be used.

[0603] Preferably, the direct dyes are chosen from among the anionic direct dyes.

[0604] Colouring materials, preferably pigments, may be present in concentrations ranging from 0.01% to 30% by weight, preferably from 0.02% to 20% by weight, more particularly from 0.05% to 15% by weight, relative to the total weight of the composition which contains them.

[0605] The direct colorant(s) may be present in concentrations ranging from 0.001% to 10% by weight, preferably from 0.005% to 5% by weight, relative to the total weight of the composition which contains them.

[0606] Preferably, the cosmetic active ingredient(s), in particular the colouring material(s), and more particularly the pigment(s), are introduced into at least one of the compositions "Cl", "C2", "C3", "C4" or "C5".

[0607] CARE ACTIVES

[0608] According to a particular embodiment, the process of the invention uses one or more active skincare ingredients.

[0609] More particularly, in the process of the invention, according to one embodiment, at least one of the compositions "Cl", "C2", "C3", "C4" or "C5" used comprises one or more active ingredients, preferably at a concentration of at least 0.01% by weight, relative to the total weight of the composition in question. In particular, the active ingredient may be at least a hydrophilic and / or a lipophilic active ingredient, and preferably a hydrophilic active ingredient.

[0610] The term “hydrophilic active” means a water-soluble or water-dispersible active capable of forming hydrogen bonds.

[0611] The cosmetic active ingredient(s) may be chosen from among: a) vitamins and their derivatives, in particular their esters, especially tocopherol (vitamin E) and its esters (such as tocopherol acetate), ascorbic acid (vitamin C) and its derivatives; b) humectants, in particular urea, hydroxyureas, glycerol, polyglycerols, glycerol glucoside, diglycerol glucoside, polyglyceryl glucosides, and xylityl glucoside, and in particular glycerol; c) C-glycoside compounds; d) antioxidant compounds; e) anti-aging actives, in particular hyaluronic acid compounds, and in particular sodium hyaluronate, retinol and its derivatives, salicylic acid compounds and in particular n-octanoyl-5-salicylic acid (capryloyl salicylic acid), caffeine, adenosine, c-beta-d-xylopyranoside-2-hydroxypropane and the sodium salt of 3-hydroxy-2-pentylcyclopentyl)acetic acid; f) skin-conditioning agents selected from allantoin, panthenol and protein hydrolysates; (g) polyphenols, in particular escin, ruscus, diosmin, hesperidin, resveratrol, and (h) mixtures thereof.

[0612] In particular, in the process of the invention, according to one embodiment, at least one of the compositions "Cl", "C2", "C3", "C4" or "C5" implemented comprises a moisturizing agent (also called a humectant). Preferably, the active ingredient is a moisturizing agent, and in particular is glycerin (glycerol).

[0613] The active ingredient(s) may in particular be present in the composition or container(s) in a content ranging from 0.01% to 30% by weight, relative to the weight of the composition, and preferably from 0.02% to 25% by weight.

[0614] UV FILTERS

[0615] According to one embodiment of the process of the invention, at least one of the compositions "Cl", "C2", "C3", "C4" or "C5" implemented includes, as a cosmetic active ingredient, at least one UV filter.

[0616] The UV filter(s) is a UV filter commonly used in cosmetics.

[0617] It can be chosen from the positive list contained in Annex VI of Regulation (EC) No 1223 / 2009, which specifies the list of UV filters authorized in cosmetics.

[0618] The UV filters suitable for the invention can be of different kinds.

[0619] They can be lipophilic, hydrophilic or insoluble organic.

[0620] By "lipophilic UV filter" is meant any cosmetic or dermatological filter capable of being completely dissolved in molecular form in a liquid oil phase or of being solubilized in colloidal form (for example in micellar form) in a liquid oil phase.

[0621] By "hydrophilic UV filter" is meant any cosmetic or dermatological filter capable of being completely dissolved in molecular form in a liquid aqueous phase or of being solubilized in colloidal form (for example in micellar form) in a liquid aqueous phase.

[0622] By "insoluble UV filter" is meant any cosmetic or dermatological filter that is neither defined as a lipophilic UV filter nor as a hydrophilic UV filter, and that is in the form of particles in a liquid aqueous or oily phase. UV filters The composition according to the invention can provide UVA and / or UVB photoprotection.

[0623] According to a preferred embodiment, the compositions, preferably cosmetic, may include at least one organic and / or mineral UV filter (filters of UV radiation from sunlight).

[0624] In particular, the UV filter(s) are selected from bis-resorcinyl triazine derivatives, dibenzoylmethane derivatives, benzylidene camphor derivatives, and mixtures thereof. Organic UV filters may also be selected from anthranilics; cinnamic derivatives; salicylic derivatives; benzophenone derivatives; phenyl benzotriazole derivatives; benzalmalonate derivatives, particularly those cited in US patent 5,624,663; phenyl benzimidazole derivatives; imidazolines; 4,4-diarylbutadiene derivatives; bis-benzoazolyl derivatives, as described in EP patents 6,693,230 and US patents 2,463,264; and p-aminobenzoic acid (PABA) derivatives. the derivatives of methylene bis-(hydroxyphenyl benzotriazole), as described in applications US 5 237 071, US 5 166 355, GB 2303549, DE 197 26 184 and EP 893 119;Benzoxazole derivatives, as described in patent applications EP 0 832 642, EP 1 027 883, EP 1 300 137 and DE 10162844; filter polymers and filter silicones such as those described in particular in application WO 93 / 04665; α-alkylstyrene derived dimers such as those described in patent application DE 19855649; 4,4-diarylbutadienes as described in applications EP 0 967 200, DE 19746654, DE 19755649, EP 1 008 586, EP 1 133 980 and EP 133 981; other merocyanine derivatives such as those described in applications WO 04006878, WO 05058269 and WO 06032741 and mixtures thereof.

[0625] According to a particular embodiment, the concentration of organic UV filters in the compositions varies from 1% to 50% by weight, preferably from 1% to 40% by weight, and even, for example, from 5% to 35% by weight, relative to the total weight of the composition.

[0626] The UV filter(s) may be mineral UV filters, which are generally pigments, preferably colorless. The pigments may be coated or uncoated.

[0627] Thus, mineral UV filters can be chosen from coated or uncoated pigments, and in particular from coated titanium oxide pigments, titanium oxides treated with silicone, uncoated titanium oxide pigments, uncoated zinc oxide pigments, coated zinc oxide pigments, uncoated cerium oxide pigments, uncoated iron oxide pigments, coated iron oxide pigments, and mixtures thereof.

[0628] According to a particular embodiment, the compositions “Cl” to “C5” are devoid of mineral UV filters.

[0629] According to a particular embodiment, the quantity of the mineral UV filter(s) present in compositions "Cl", "C2", "C3", "C4" or "C5" can range from 0.01% to 20% by weight, relative to the total weight of the composition containing them. For example, it ranges from 1% to 15% by weight, relative to the total weight of the composition.

[0630] According to a particular embodiment, at least one of the compositions "Cl" to "C5" further comprises one or more organic UV filters and one or more mineral UV filters.

[0631] According to a particular embodiment, the compositions comprise an association of UV filters as described in French patent FR 2 977 490, application WO 2013 / 004777 or US application 2014 / 0134120.

[0632] Preferably, the process for treating keratinous materials, in particular keratinous fibers, and the compositions "Cl", "C2", "C3", "C4" or "C5" comprise the application of or comprise one or more coloring materials selected from pigments, direct dyes and their mixtures, preferably pigments; more preferably the pigment(s) of the invention are selected from carbon black, iron oxides in particular yellow, red and black and micas coated with iron oxide, triarylmethane pigments in particular blue and violet such as BLUE 1 LAKE, azo pigments in particular red such as D&C RED 7, the alkali metal salt of lithol red such as the calcium salt of lithol red B, even more preferably red iron oxides, yellow iron oxides and azo pigments in particular red such as D&C RED 7.

[0633] FAT PHASE - FAT BODY

[0634] According to a particular embodiment, the process of the invention comprises the application of v) one or more fatty substances, in particular one or more oils.

[0635] In particular, at least one of the compositions “Cl”, “C2”, “C3”, “C4” or “C5” implemented in the process of the invention contains a fatty phase.

[0636] In particular, at least one of the compositions "Cl", "C2", "C3", "C4" or "C5", implemented in the process of the invention comprises one or more fatty substances, distinct from compounds i), in particular one or more oils, preferably volatile.

[0637] By "oil" is meant a liquid fat at room temperature (20 °C) and atmospheric pressure (760 mm Hg).

[0638] By "hydrocarbon oil" is meant an oil formed essentially, or even composed, of carbon and hydrogen atoms, and possibly of oxygen and nitrogen atoms, and not containing silicon or fluorine atoms. It may contain alcohol, ester, ether, carboxylic acid, amine and / or amide groups.

[0639] According to one embodiment of the invention, the oil(s) v) is / are chosen from volatile oils, in particular:

[0640] - hydrocarbon oils having 8 to 16 carbon atoms, in particular C8-Ci6 branched alkanes, in particular isoalkanes, more particularly iso-alkanes (also called isoparaffins), preferably Ci3-Ci6 Isoparaffin, isododecane, isodecane, isohexadecane, 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), linear alkanes, in particular Cn-Ci6, alone or in mixtures, in particular hexane, decane, undecane, tridecane, isoparaffins in particular n-dodecane (Ci2) and n-tetradecane (CM), the undecane-tridecane mixture, mixtures of n-undecane (Cn) and n-tridecane (Cn), and mixtures thereof as well as mixtures of n-undecane (Cn) and n-tridecane (Ci3), and non-aromatic cyclic alkanes, in volatile C5-Ci2;

[0641] - short-chain esters having from 3 to 8 carbon atoms in total, in particular ethyl acetate, methyl acetate, propyl acetate, n-butyl acetate;

[0642] - hydrocarbon oils with a carbonate structure of R'i-OC(O)-O-R'2 in which R'i and R'2 independently designate a linear, branched or cyclic C4-C8 alkyl group, preferably a C4-C8 alkyl group, advantageously, more preferably chosen from dibutylcarbonate or dipentylcarbonate;

[0643] - RrO-R2 ether oils, in which Ri and R2 denote, independently of each other, a linear, branched or cyclic C4-C8 alkyl group, preferably a C4-C8 alkyl group;

[0644] - silicone oils, in particular comprising 2 to 7 silicon atoms, and comprising, possibly, alkyl or alkoxy groups having from 1 to 10 carbon atoms, in particular dimethicones of viscosity 5 and 6 cSt, cyclopentadimethyl isiloxane, dodecamethylpentasiloxane, cyclohexadimethylsiloxane, octamethyl cyclotetrasiloxane, decamethyl cyclopentasiloxane, dodecamethyl cyclohexasiloxane, heptamethyl hexyltrisiloxane, heptamethyloctyl trisiloxane, hexamethyl disiloxane, octamethyl trisiloxane, decamethyl tetrasiloxane, dodecamethyl pentasiloxane, and mixtures thereof;

[0645] more preferably the volatile oil(s) v) are chosen from among the C8-Ci6 alkanes, in particular branched, preferably isododecane.

[0646] In particular, at least one of the compositions “Cl”, “C2”, “C3”, “C4” or “C5” used in the process according to the invention comprises one or more non-volatile oil(s), preferably chosen from:

[0647] - non-volatile fluorinated oils, in particular selected from fluorinated polyethers, fluorosilicone oils, fluorinated silicones;

[0648] - non-volatile silicone oils, in particular selected from silicones non-volatile substances with the following INCI names: dimethicone, dimethiconol, trimethyl pentaphenyl trisiloxane, tetramethyl tetraphenyl trisiloxane, diphenyl dimethicone, trimethylsiloxyphenyl dimethicone, phenyltrimethicone, diphenylsiloxy phenyl trimethicone, and their mixtures;

[0649] - non-volatile non-polar hydrocarbon oils, in particular selected from linear or branched compounds, of mineral or synthetic origin: i) paraffin oil, ii) squalane, isoeicosane, iii) mixtures of linear hydrocarbons, saturated, more particularly in Ci5-C28, in particular mixtures whose INCI names are (Ci5-Ci9)alkane, (Ci8-C2i)alkane, (C2i-C28)alkane, iv) polybutenes, hydrogenated or not; v) polyisobutenes, hydrogenated or not, preferably hydrogenated, vi) polydecenes, hydrogenated or not, vii) decene / butene copolymers, butene / isobutene copolymers and viii) their mixtures;

[0650] - non-volatile polar hydrocarbon oils that may be selected from:

[0651] (i) fatty alcohols, saturated, unsaturated, linear or branched, of C10-C26, preferably mono-alcohols; in particular, C10-C26 alcohols are fatty alcohols, preferably branched when they comprise at least 16 carbon atoms; preferably, the fatty alcohol comprises from 10 to 24 carbon atoms, and more preferably from 12 to 22 carbon atoms, in particular lauryl, isostearyl, oleic alcohol, 2-butyloctanol, 2-undecyl pentadecanol, 2-hexyldecyl alcohol, isocetyl alcohol, octyldodecanol and mixtures thereof;

[0652] ii) triglycerides consisting of esters of fatty acids and glycerol, in particular of which the fatty acids may have chain lengths ranging from C4 to C36, and in particular from C[8 to C36, these oils being linear or branched, saturated or unsaturated; by way of examples, one may mention in particular heptanoic or octanoic triglycerides, caprylic / capric acid triglycerides; vegetable oils such as wheat germ, sunflower, grapeseed, sesame, corn, apricot kernel, castor, shea, avocado, olive, soybean, sweet almond, palm, rapeseed, cottonseed, hazelnut, macadamia, jojoba, alfalfa, poppy, pumpkin, squash, blackcurrant, evening primrose, millet, barley, quinoa, rye, safflower, candlenut, passionflower, rosehip, peanut, coconut, argan, passionflower, kaya; the liquid fraction of shea butter, and the liquid fraction of cocoa butter;as well as mixtures thereof;

[0653] iii) linear aliphatic hydrocarbon esters of formula RC(O)-OR' in which RC(O)-O- represents the carboxylic acid remainder comprising 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 in particular ethylene glycol or propylene glycol; the total number of carbon atoms being in particular at least 10;in particular selected from isoamyl laurate, cetostearyl octanoate, isopropyl myristate, isopropyl palmitate, isopropyl stearate or isostearate, ethyl palmitate, 2-ethylhexyl palmitate, isostearyl isostearate, octyl stearate, isostearyl heptanoate, octanoates, decanoates or ricinoleates of alcohols or polyalcohols such as propylene glycol dioctanoate, cetyl octanoate, tridecyl octanoate, ethyl 2-hexyl palmitate, alkyl benzoate, polyethylene glycol diheptanoate, propylene glycol diethyl 2-hexanoate and mixtures thereof, hexyl laurate, neopentanic acid esters such as isodecyl neopentanate, isotridecyl neopentanate, isostearyl neopentanate, octyl-2-docecyl neopentanate, isononanoic acid esters, in particular isononyl isononanoate, isotridecyl isononanoate, octyl isononanoate, oleyl erucate;lauroyl isopropyl sarcosinate, diisopropyl sebacate, isocetyl stearate, isodecyl neopentanoate, isostearyl behenate, myristyl myristate;

[0654] iv) hydroxylated esters, in particular polyglycerol-2 triisostearate;

[0655] v) aromatic esters, in particular tridecyl trimellitate, alcohol benzoate in C12-C15, the 2-phenyl ethyl ester of benzoic acid, butyl octyl salicylate;

[0656] vi) linear fatty acid esters having a total carbon number from 35 to 70, in particular pentaerythrityl tetrapelargonate;

[0657] vii) C24-C28 branched fatty alcohol or fatty acid esters, in particular triisoarachidyl citrate, pentaerythrityl tetraisononanoate, glyceryl triisostearate, glyceryl tridecyl-2-tetradecanoate, pentaerythrityl tetraisostearate, polyglyceryl-2 tetraisostearate or pentaerythrityl tetradecanoate;

[0658] viii) polyesters obtained by condensation of dimer and / or trimer of unsaturated fatty acid and diol, in particular of INCI name dilinoleic acid / butanediol copolymer, dilinoleic acid / propanediol copolymer; polyesters obtained by condensation of fatty acid dimer and diol dimer, in particular dilinoleyl dimer dilinoleate;

[0659] ix) synthetic ethers having 10 to 40 carbon atoms, in particular dicaprylyl ether;

[0660] x) di-alkyl carbonates, the 2 alkyl chains being either identical or different, in particular dicaprylyl carbonate;

[0661] xi) vinylpyrrolidone copolymers, in particular the vinylpyrrolidone / 1-hexadecene copolymer; and

[0662] xii) their mixtures;

[0663] - non-volatile carbonate oils can be selected from carbonates of formula R8-OC(O)-O-R9, with R8 and R9, identical or different, representing an alkyl chain from C4 to C12, and preferably from C6 to C10, linear or branched; the carbonate oils may be dicaprylyl carbonate (or dioctyl carbonate), di(ethyl-2-hexyl) carbonate, dipropylheptyl carbonate, dibutyl carbonate; di-neopentyl carbonate; dipentyl carbonate; dineoheptyl carbonate; diheptyl carbonate; di-isononyl carbonate; or di-nonyl carbonate; and preferably dioctyl carbonate;

[0664] - oils called non-volatile ether oil of formula RrO-R2 in which Ri and R2 independently denote a linear, branched, or cyclic C6-C24 alkyl group, preferably a C6-Ci8 alkyl group, and preferably a C8-Ci2 alkyl group. It may be preferable for Ri and R2 to be identical. Examples of linear alkyl groups include hexyl, heptyl, octyl, nonyl, decyl, undodyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, eicosyl, behenyl, docosyl, tricosyl, and tetracosyl groups.Examples of branched alkyl groups include 1,1-dimethylpropyl, 3-methylhexyl, 5-methylhexyl, ethylhexyl, 2-ethylhexyl, 5-methyloctyl, 1-ethylhexyl, 1-butylpentyl, 2-butyloctyl, isotridecyl, 2-pentylnonyl, 2-hexyldecyl, isostearyl, 2-heptylundecyl, 2-octyldodecyl, 1,3-dimethylbutyl, 1-(l-methylethyl)-2-methylpropyl, 1,1,3,3-tetramethylbutyl, 3,5,5-trimethylhexyl, and l-(2-methylpropyl)-3-methylbutyl. 3,7-dimethyloctyl, and a 2-(l,3,3-trimethylbutyl)-5,7,7-trimethyloctyl group.Examples of cyclic alkyl groups include cyclohexyl, 3-methylcyclohexyl, 3,3,5-trimethylcyclohexyl, dilaury ether, diisostearyl ether, dioctyl ether, nonylphenyl ether, dodecyl dimethyl butyl ether, cetyl dimethyl butyl ether, cetyl isobutyl ether, and mixtures thereof.

[0665] Preferably, the non-volatile oil(s) is / are chosen from among polyisobutenes, hydrogenated or not, preferably hydrogenated, in particular the non-volatile compounds of the Parléam® range; C15-C19 Alkane mixtures, and from among linear aliphatic hydrocarbon esters of formula RC(O)-OR' in which RC(O)-O represents a carboxylic acid residue comprising from 2 to 40 carbon atoms, and R' represents a hydrocarbon chain containing from 1 to 40 carbon atoms, as defined previously, in particular isononyl isononanoate.

[0666] More preferably, the process of the invention uses one or more hydrocarbon oils having 8 to 16 carbon atoms, and in particular C8-Ci6 branched alkanes, in particular iso-alkanes, preferably Ci3-Ci6 Isoparaffin, isododecane, isodecane, isohexadecane, alone or in mixtures, and more preferably isododecane.

[0667] According to a preferred embodiment, the process of the invention uses one or more fatty substances v), distinct from the polyesters of formula (I), in particular at least one oil, preferably at least one volatile oil, more preferably at least one hydrocarbon volatile oil.

[0668] In particular, the quantity of oil(s), distinct from the compounds i), in at least one of the compositions "Cl", "C2", "C3", "C4" or "C5"", implemented in the process according to the invention, ranges from 1% to 99% by weight, relative to the total weight of the composition, more particularly from 2% to 98% by weight, preferably from 3% to 97%, better from 5% to 96% by weight, relative to the total weight of the composition.

[0669] According to another particular embodiment, the process of the invention does not use fats v) separate from the compounds of formula (I).

[0670] According to yet another embodiment, at least one of the compositions "Cl", "C2", "C3", "C4" or "C5"", implemented in the process according to the invention, contains a mixture of fatty substances v) distinct from the compounds i), and selected from mixtures of at least one volatile oil, preferably hydrocarbon, and at least one non-volatile oil, such as octyldodecanol.

[0671] COMPOSITIONS

[0672] Another object of the invention is compositions, in particular cosmetics, containing at least one polyester of formula (I) and its optical, geometric and / or solvated isomers, such as hydrates, more particularly compositions, in particular cosmetics, containing at least one polyester of formula (I), as described above.

[0673] Another object of the invention is compositions, in particular cosmetics, containing at least one compound selected from the PI to P7 polyesters, as described above, as well as their salts, isomers, solvated.

[0674] According to a particular embodiment, the process for treating keratinous materials, particularly for the care and / or makeup of skin, lips, eyelashes and / or eyebrows and / or for the care, styling and / or coloring of keratinous fibers, preferably hair, according to the invention, uses water or an organic solvent. Thus, according to one variant, at least one of the compositions "Cl" to "C5" used in the process of the invention comprises water. According to In this variant, the compositions "Cl", "C2", "C3", "C4" and / or "C5" are aqueous or hydroalcoholic compositions.

[0675] According to one embodiment, the process for treating keratinous materials, particularly for the care and / or makeup of skin, lips, eyelashes and / or eyebrows and / or for the care, styling and / or coloring of keratinous fibers, preferably hair, according to the invention, does not use water. Thus, according to this variant, the compositions "C1", "C2", "C3", "C4" and / or "C5" are anhydrous compositions.

[0676] According to a particular embodiment, at least one of the compositions "Cl", "C2", "C3", "C4" and / or "C5" comprise an isododecane / ethanol mixture, in particular in a volume ratio of between 1 / 99 and 99 / 1, more particularly between 5 / 95 and 95 / 5.

[0677] According to a particular embodiment, at least one of the compositions "Cl", "C2", "C3", "C4" and / or "C5" comprise an isododecane / octyldodecanol mixture, in particular in a volume ratio of between 1 / 99 and 99 / 1, more particularly between 5 / 95 and 95 / 5.

[0678] According to a particular embodiment, at least one of the compositions "Cl", "C2", "C3", "C4" or "C5" may be in the form of a water-in-oil emulsion or an oil-in-water emulsion.

[0679] According to a particular embodiment, the compositions “Cl”, “C4” or “C5” may be in anhydrous form, water-in-oil emulsion or oil-in-water emulsion.

[0680] According to a particular embodiment, composition "C4" is anhydrous. In particular, composition "C4" is anhydrous, and it comprises at least one oil, in particular volatile, preferably isododecane.

[0681] According to another particular embodiment, composition “C4” comprises water. In particular, composition “C4” comprises water, and optionally at least one volatile or non-volatile oil, and / or at least one Ci-C4 alcohol such as ethanol or isopropanol, and / or at least one non-volatile oil.

[0682] The compositions “Cl” to “C5” implemented in the process of the invention may further comprise one or more solvents, distinct from water.

[0683] According to a particular embodiment of the invention, the polyester(s) of formula (I) as defined above are implemented in a medium containing at least one solvent, preferably at least one polar and / or protic solvent, other than water.

[0684] According to this embodiment, the composition “Cl”, “C2”, “C3”, “C4” and / or “C5” implemented in the process of the invention comprises one or more solvents, preferably one or more polar and / or protic solvents, other than water.

[0685] Preferably, the composition “Cl”, “C2”, “C3”, “C4” and / or “C5” implemented in the process of the invention comprises at least one polar and / or protic solvent chosen from monoalcohols having 2 to 6 carbon atoms, in particular chosen from ethanol, propanol, n-butanol, isopropanol, isobutanol, tert-butanol, pentanol, hexanol, preferably n-butanol or ethanol, and even more preferably ethanol.

[0686] According to a preferred embodiment, the composition "Cl", "C2", "C3", "C4" and / or "C5" implemented in the process of the invention comprises at least one volatile or non-volatile oil, and / or at least one Ci-C4 alcohol such as ethanol or isopropanol, preferably comprising at least one solvent selected from isododecane, octyl-2 dodecanol, isononyl isononanoate, ethanol, and mixtures thereof.

[0687] According to one embodiment, the composition “Cl”, “C2”, “C3”, “C4” and / or “C5” implemented in the process of the invention comprises one or more solvents distinct from water in a content of less than 95% by weight, more preferably less than 92% by weight, relative to the total weight of the composition.

[0688] According to one embodiment, the composition “C2” or “C3” or “C4” is anhydrous.

[0689] According to another embodiment, the composition “C4” is aqueous.

[0690] As an organic solvent, we can also mention water-miscible polyols at room temperature (25 °C), in particular chosen from polyols having from 2 to 10 carbon atoms, preferably having from 2 to 6 carbon atoms, such as glycerin, propylene glycol, 1,3-propanediol, butylene glycol, pentylene glycol, hexylene glycol, dipropylene glycol, diethylene glycol, diglycerin; polyol ethers such as 2-butoxyethanol, propylene glycol monomethyl ether, diethylene glycol monoethyl ether and monomethyl ether, as well as aromatic alcohols such as benzyl alcohol, and mixtures thereof.

[0691] According to a particular embodiment, the composition further comprises one or more polyols, in particular chosen from polyols having in particular from 2 to 10 carbon atoms, preferably having from 2 to 6 carbon atoms, preferably glycerin.

[0692] The compositions “Cl”, “C2”, “C3”, “C4” or “C5” implemented in the process of the invention may further comprise one or more adjuvants commonly used in cosmetics, in particular chosen from thickeners, film-forming agents, gelling agents, trace elements, softeners, sequestrants, perfumes, alkalizing or acidifying agents, dispersing agents, preservatives, fillers, surfactants, propellants, polar additives, polymers, or mixtures thereof.

[0693] Another object of the invention is a composition, referred to as "C2", in particular cosmetic, comprising i) at least one polyester of formula (I) as well as its optical, geometric isomers, its organic or mineral acid or base salts, and / or solvates, such as hydrates, as defined above, ii) at least one crosslinking agent, in particular as defined above, and optionally iv) at least one cosmetic active, in particular as defined above; preferably, the "C2" composition does not comprise iv) any cosmetic active.

[0694] Another object of the invention is a composition, referred to as "C3", in particular cosmetic, comprising i) at least one polyester of formula (I) as well as its optical, geometric isomers, its organic or mineral acid or base salts, and / or solvated, such as hydrates, as defined above, ii) at least one crosslinking agent, in particular as defined above, and iv) at least one cosmetic active, in particular as defined above, preferably chosen from a) coloring materials, preferably chosen from pigments, direct colorants and their mixtures, and more preferably from pigments.

[0695] Another object of the invention is the cosmetic use of the composition “C2” as defined above, for the treatment of keratinous materials, in particular for the care and / or makeup of the skin, lips, eyelashes and / or eyebrows and / or for the care, styling and / or coloring of keratinous fibers, preferably hair.

[0696] Another object of the invention is the cosmetic use of the composition “C3” as defined above, for the treatment of keratinous materials, in particular for the care and / or makeup of the skin, lips, eyelashes and / or eyebrows and / or for the care, styling and / or coloring of keratinous fibers, preferably hair.

[0697] A composition “Cl”, “C2”, “C3”, “C4” or “C5” is generally suitable for application on keratinous materials, in particular application on skin, lips and / or keratinous fibers, and therefore generally comprises a physiologically acceptable medium, i.e. compatible with keratinous materials, in particular application on skin, lips and / or keratinous fibers, including human keratinous fibers such as hair.

[0698] The physiologically acceptable medium is preferably a cosmetically acceptable medium, that is to say, one which has a pleasant colour, odor and feel and does not generate unacceptable discomforts, that is to say, tingling, pulling, which may deter the user from applying this composition.

[0699] A composition “Cl”, “C2”, “C3”, “C4” or “C5” may be in the form of a makeup product, in particular a colored one, a skin product, in particular a foundation, possibly having skincare properties, a blush, a face paint cheeks or eyelids, an under-eye concealer, an eyeliner; a lip makeup product such as lipstick, possibly with conditioning properties, lip gloss, lip pencils; a makeup product for skin appendages such as nails, eyelashes especially in the form of mascara, eyebrows and hair, a temporary tattoo product for the skin of the body.

[0700] According to a particular embodiment, a composition "Cl", "C2", "C3", "C4" or "C5" is presented in the form:

[0701] - either a colored lip product; - either a skincare product, possibly coloured, in particular a cream or fluid with moisturising and / or filling and / or tightening properties; or - either a hair product, in particular a hair coloring product or a styling product, especially one without coloring matter, such as hairspray, or a so-called "styling" product such as mousse or gel.

[0702] KIT

[0703] According to yet another aspect, the present invention also relates to a kit or device, particularly a cosmetic one, with several compartments comprising: - at least one compartment containing at least i) at least one polyester of formula (I), as defined above, and possibly iv) at least one cosmetic active ingredient, in particular as defined above, and in particular comprising a "Cl" composition as defined above; - at least one compartment separate from that which contains i) and containing ii) at least one crosslinking agent, in particular as defined above, and possibly iv) at least one cosmetic active ingredient, in particular as defined above, and in particular comprising a "C4" composition as defined above; and - optionally, at least one compartment separate from those which contain i) and ii), and containing iv) at least one cosmetic active ingredient, in particular as defined above, identical or different from that / those possibly contained in the compartments comprising i) and ii).

[0704] Preferably, the compartment comprising at least i), in particular a "Cl" composition, does not comprise a crosslinking agent ii).

[0705] Preferably, the compartment comprising at least one crosslinking agent ii), in particular a “C4” composition, does not contain i) polyester of formula (I).

[0706] Throughout the description, including the claims, the expression "comprising one" shall be understood as synonymous with "comprising at least one", unless otherwise specified.

[0707] The expressions "between ... and ...", "includes from ... to ...", "made up of ... to ...", and "ranging from ... to ..." are equivalent and are meant to mean that the boundaries are included, unless otherwise stated.

[0708] The expression "at least one" is equivalent to "one or more".

[0709] The invention is illustrated in more detail by the non-limiting examples presented below. Examples Measurement and evaluation methods

[0710] SKIN APPLICATION

[0711] a) One-step protocol

[0712] The polyester(s) of formula (I) with acetoacetate functional groups or the alkyd resin(s) without acetoacetate functional groups, a pigment, and a solvent are homogenized together in a Speedmixer (a mixing device that uses centrifugal force) for 2 minutes at 3,500 rpm and at room temperature. The crosslinking agent(s), and optionally the catalyst, are introduced before or after the homogenization step.

[0713] The compositions are applied to a Bioskin-type vitro support from Maprecos (Bioskin plate #10) (elastomer skin-simulating support) using a film puller (wet thickness 100 µm). The deposit is left to dry for 24 hours.

[0714] After 24 hours of drying, the evaluations of the deposits are carried out according to the protocols described below.

[0715] b) Two-step protocol

[0716] A first composition, referred to as the "base coat," comprising the formula (I) polyester(s) with acetoacetate functional groups or the alkyd resin(s) without acetoacetate functional groups, a pigment, a solvent, and optionally an oil, preferably non-volatile, such as 2-octyl-l-dodecanol or isononyl isononanoate, is prepared using a Speedmixer (a mixing device that uses centrifugal force) for 2 minutes at 3,500 rpm and at room temperature. The composition is applied to a Maprecos Bioskin-type vitro substrate (Bioskin plate #10) (elastomeric skin-simulating substrate) using a film puller (wet thickness 100 µm). The deposit is allowed to dry for 24 hours.

[0717] After this first step, a second composition, called "top coat", comprising a crosslinker and possibly at least one oil, is applied in the same way.

[0718] The deposit is left to dry for 24 hours.

[0719] After 24 hours of drying, the evaluations of the deposits are carried out according to the protocols described below.

[0720] SCOTCH RESISTANCE

[0721] A piece of Scotch tape (3M Scotch® Magic™ 810; 1 = 19 mm, L = 5 cm) is applied to the formulation film obtained after 24 hours of drying. A weight of approximately 1070 g is applied to the piece of tape for 30 seconds. The piece of tape is then removed and placed on a microscope slide to observe the result. The adhesion of the film to the substrate is thus evaluated.

[0722] RESISTANCE TO OLIVE OIL / SEBUM / WATER

[0723] 0.5 mL of olive oil, sebum or water is applied to the formulation film The product is obtained after 24 hours of drying. After 5 minutes, the olive oil, sebum, or water is removed by 15 passes with a cotton ball. This allows observation of the film's deterioration following contact with the droplet of the irritant.

[0724] In the case of a two-step protocol, for each combination, evaluations are conducted for the "base coat" composition alone after drying, and on the "base coat" + "top coat" composition system after drying, the objective being to observe the cosmetic properties improved by such combinations.

[0725] Resistance is evaluated according to the following scale:

[0726] +++ : Cosmetic property evaluated as very effective, no aggression to the deposit which is as it was originally;

[0727] ++: Cosmetic property rated as moderately effective, some transfer but the deposit is as it was originally;

[0728] + : Cosmetic property evaluated as performing poorly, the deposit is slightly altered and it is observed some transfer;

[0729] 0: Cosmetic property evaluated as not performing, the application is completely degraded and there is a lot of transfer onto the cotton.

[0730] BIOSKIN FORMULATION FRAGMENTATION TEST

[0731] As with the tests for resistance to olive oil / sebum / water and to Scotch tape, films are applied to a sample of Bioskin. After a day of drying, the Bioskin plate is stretched 10 times by hand.

[0732] Next, the result is observed on the film (fragmentation or not).

[0733] ​​The evaluation is carried out as follows:

[0734] +++ : Cosmetic property evaluated as very effective;

[0735] ++ : Cosmetic property evaluated as moderately performing;

[0736] + : Cosmetic property evaluated as performing poorly;

[0737] 0: Cosmetic property evaluated as not performing.

[0738] PROTOCOL FOR GLOSS RETENTION

[0739] The compositions, comprising one or more formula (I) polyesters with acetoacetate functions, or one or more alkyd resins not bearing acetoacetate functions, and / or a crosslinker and a solvent, are applied using an applicator (wet thickness 100 pm) on a contrast chart (reference: byko-charts Opacity chart #2810).

[0740] Using a glossmeter, the gloss is measured at 20° (angle of incidence) of the card and then the gloss of the deposit 2 hours and then 24 hours after application.

[0741] Once dry, 0.5 mL of water are added and left for 5 minutes.

[0742] The drops of aggressor are then rubbed with cotton (15 passes) and the measurement of the gloss / matteness is carried out on the aggressed area (average of 5 measurements).

[0743] HAIR COLOUR APPLICATION

[0744] The hair coloring evaluation protocol is detailed below:

[0745] The evaluations are conducted according to three different protocols: in 1, 2 or 3 step(s), each on strands of natural hair that are 90% white.

[0746] a) One-step protocol

[0747] The polyester(s) of formula (I) with acetoacetate functions, the pigment(s) and optionally the crosslinking agents, are mixed together before application. The system remains fluid long enough to allow application to the substrate.

[0748] The composition is applied to strands of dry natural hair that are 90% white, at a rate of 1 g of composition per gram of strand.

[0749] The hair strands are left at room temperature for 5 minutes.

[0750] The hair strands are then combed and blow-dried for 3 minutes.

[0751] The hair strands are left at room temperature for 24 hours. The hair is colored evenly and intensely.

[0752] The hair strands thus coloured are then subjected to a test of several repeated shampoos in order to evaluate the tenacity (the persistence) of the colour obtained to the shampoos, according to the shampoo protocol described below.

[0753] b) Two-step protocol

[0754] A first composition, called a "base coat," is applied to strands of dry, natural hair that is 90% white, at a rate of 0.5 g of the composition per gram of strand. The strands are then combed. This coating is applied to the keratinous materials and then left to dry for 3 hours at room temperature (25 °C). This drying step can be accelerated by subjecting the keratinous material to heat after application, for example, with a hairdryer.

[0755] After this first step, a second composition, called "top coat", is applied to the strand of hair, at a rate of 0.5 g per gram of strand.

[0756] After application, the hair strands are dried with a hairdryer.

[0757] The hair strands are left at room temperature for 24 hours under a fume hood. The hair is colored evenly and intensely.

[0758] The hair strands thus coloured are then subjected to a test of several repeated shampoos in order to evaluate the tenacity (the persistence) of the colour obtained to the shampoos, according to the shampoo protocol described below.

[0759] c) 3-step protocol

[0760] A first composition containing one or more pigments alone or in the presence of one or more crosslinkers carried in an organic solvent is applied to strands of dry natural hair that are 90% white, at a rate of 0.5 g of composition per gram of strand, then the strands are dried with a hairdryer.

[0761] A second composition, called "base coat", is applied to this coloured strand, at a rate of 0.5 g of composition per gram of strand, then the strands are dried with a hairdryer before being left to rest for 3 hours.

[0762] After this second step, a third composition, called "top coat", is applied to the strand of hair, at a rate of 0.5 g per gram of strand.

[0763] After application, the hair strands are dried with a hairdryer.

[0764] The hair strands are left at room temperature for 24 hours under a fume hood. The hair is colored evenly and intensely.

[0765] The hair strands thus coloured are then subjected to a test of several repeated shampoos in order to evaluate the tenacity (the persistence) of the colour obtained to the shampoos, according to the shampoo protocol described below.

[0766] SHAMPOO PROTOCOL

[0767] The colored hair strands are combed, moistened under water at 35°C before being passed between the fingers 5 times for 5 seconds. The hair strands are then squeezed between two fingers.

[0768] A standard shampoo (Garnier Ultra Doux) is applied evenly to the colored strands at a rate of 0.4 g of standard shampoo per gram of strands, gently massaging the strands of hair along their length (6 passes) for 15 seconds, from root to tip.

[0769] The strands of hair are then placed in a watch glass and left for 1 minute.

[0770] Next, the hair strands are rinsed with water by passing the strand between the fingers (15 passes). The hair strands are then squeezed dry between two fingers before the next shampoo.

[0771] Once the tests of several shampoos have been carried out, the strands of hair are combed and dried with a hairdryer.

[0772] REMAINENCE PROTOCOL

[0773] The persistence of the color of the highlights was evaluated in the CIE L*a*b* system, using a Minolta Spectrophotometer CM3600A colorimeter (illuminant D65, angle 10°, specular component included).

[0774] In this L*a*b* system, L* represents the intensity of the color, a* indicates the green / red color axis and b* the blue / yellow color axis.

[0775] The permanence of the color is assessed by the color difference AE between the colored strands before shampooing, and then after 1 and 3 shampoos according to the protocol described above. The lower the AE value, the more the color remains after shampooing.

[0776] The value of AE is calculated according to the following equation:

[0777] [Math.l] AE =

[0778] In this equation, L*a*b* represent the values ​​measured after hair coloring and after shampooing, and L0*a0*b0* represent the values ​​measured after hair coloring but before shampooing.

[0779] STEAMPOD PROTOCOL

[0780] The polyester(s) of formula (I) according to the invention and the crosslinking agents are mixed together before application. The system remains fluid long enough to allow application to the substrate.

[0781] The composition is applied to strands of dry natural hair that are 90% white, at a rate of 1 g of composition per gram of strand.

[0782] The hair strands are then combed and blow-dried for 1 minute and 30 seconds, then a steam straightener (STEAMPOD) is applied to said hair strands with 5 passes at a temperature of 210 °C.

[0783] The hair strands are then subjected to a test of several repeated shampoos, according to the shampoo protocol described above.

[0784] HAIR STYLING EVALUATION PROTOCOL

[0785] The styling evaluation protocol is detailed below:

[0786] A lock of hair (90% Natural White BN hair, length 20.5 cm) is wrapped around a brush (approximate diameter of 2 cm over a length of 3 cm).

[0787] 2 g of a solution containing the formulas described below are sprayed onto The wick is weighed before and after application. Approximately 0.5 g of each composition is actually deposited on the wick. The wick is left at room temperature at 25 °C.

[0788] After 24 hours, the strand is removed from the brush and hung. The length of the strand is then measured. After another 24 hours of suspension, the length of the strand is measured again.

[0789] A comparison of loop retention is carried out between the compositions according to the invention and the comparative compositions.

[0790] Example 1: Synthesis of a polyester with acetoacetate groups (polyester 1) Example 1.1 Alkyd resin 1 - not part of the invention

[0791] Alkyd resin 1 was prepared from the reagents and contents indicated in the table below:

[0792] [Tables 1] Reagents Mass Percentage (%) (relative to the total weight of the alkyd resin obtained) Isostearic acid (fiisæw1* 3505 .par CROZX.4) 55. Pentaerythritol. 23 Sebacic acid 77 Table 1

[0793] In a 0.5 L reactor equipped with mechanical stirring, a distillation column, and an argon inlet, 88 g of sebacic acid, 92 g of pentaerythritol, and 220 g of isostearic acid are introduced. The reactor is maintained under an argon atmosphere throughout the bubbling synthesis. The reaction mixture is heated to 180 °C for 1 hour, then to 230 °C for 7 hours, before cooling to room temperature. The alkyd resin is obtained as a cloudy, viscous oil at room temperature.

[0794] The acid value la and the hydroxyl value IOH are measured.

[0795] Ia = 2 mg KOH / g

[0796] Ioh= 150 mg KOH / g Example 1.2 Polyester 1 - invention

[0797] Polyester 1 was prepared from the reagents and contents indicated in the table below:

[0798] [Tables2] Reagents Mass Percentage (%) (relative to the total weight of the alkyd resin obtained) Alkyd Resin 1 67.6 Tert-Butylacetoacetate 32.4 Table 2

[0799] In a 250 mL round-bottom flask equipped with a mechanical stirrer and a distillation column, 100 g of the alkyd resin of Example 1.1 and 48 g of tert-butyl acetoacetate are introduced. The reaction mixture is heated to 140 °C - 150 °C using a oil bath. After 5 hours, the reaction mixture is placed under continuous vacuum at 150 °C for 1 hour. A viscous, amber-colored oil is obtained.

[0800] Analysis by 'H NMR spectrometry shows the presence of AcAc groups on the polyester obtained.

[0801] Example 2: Synthesis of a polyester with acetoacetate groups (polyester 2) Example 2.1 Alkyd resin 2 - not part of the invention

[0802] Alkyd resin 2 was prepared from the reagents and contents indicated in the table below:

[0803] [Tables3] Reagents Mass Percentage (%) (relative to the total weight of the alkyd resin obtained) Isostearic acid (Prisorme™ 3505 marketed by CRODA) 54 Pentaerythritol 0.23 Homophthalic acid 0.23 Table 3

[0804] In a 0.5 L reactor equipped with mechanical stirring, a distillation column, and an argon inlet, 92 g of homophthalic acid, 92 g of pentaerythritol, and 216 g of isostearic acid are introduced. The reaction mixture is heated to 190 °C for 1 hour, then to 230 °C for 10 hours, before cooling to room temperature. The alkyd resin is obtained as a dark amber polymer.

[0805] The acid value la and the hydroxyl value IOH are measured.

[0806] Ia = 3.7 mg KOH / g

[0807] I0H= 140 mg KOH / g Example 2.2 Polyester 2 - invention

[0808] Polyester 2 was prepared from the reagents and contents indicated in the table below:

[0809] [Tables4] Reagents Mass Percentage (%) (relative to the total weight of the alkyd resin obtained) Alkyd Resin 2 71.66 tert-butyl acetoacetate 28.34 Table 4

[0810] In a 500 mL round-bottom flask equipped with a mechanical stirrer and a distillation column, 300 g of the alkyd resin of Example 2.1 and 118.65 g of tert-butyl acetoacetate are introduced. The reaction mixture is heated to 150 °C using a oil bath. After 5 hours, the reaction medium is placed under continuous vacuum at 150 °C for 1 hour. An amber-colored polymer is obtained.

[0811] Analysis by 'H NMR spectrometry shows the presence of AcAc groups on the polyester obtained.

[0812] Example 3: Synthesis of a polyester with acetoacetate functions (polyester 3) Example 3.1 Alkyd resin 3 - not part of the invention

[0813] Alkyd resin 3 was prepared from the reagents and contents indicated in the table below:

[0814] [Tables5] Reagents Mass Percentage (%) (relative to the total weight of the alkyd resin obtained) Octanoic acid 42.13 Xvlitol 29.14 Sebacic acid 28.73 Table 5

[0815] a) In a 0.5 L reactor equipped with mechanical stirring, a distillation column, and an argon inlet, 87.42 g of xylitol and 126.39 g of octanoic acid are introduced. The reaction mixture is gradually heated to a temperature of 180 °C in 1 hour, and then the temperature is maintained at 180 °C for 5 hours.

[0816] The acid value la is measured: la = 27.82 mg KOH / g.

[0817] b) 86.19 g of sebacic acid are introduced into the reactor. The heating is maintained at 180 °C for 13 hours, then the medium is heated at 180 °C for 10 hours under vacuum (20 mbar).

[0818] Alkyd resin is obtained in the form of a viscous amber oil.

[0819] The final acid value and the hydroxyl value IOH are measured.

[0820] la = 12 mg KOH / g

[0821] I0H= 206 mg KOH / g. Example 3.2 Polyester 3 - invention

[0822] Polyester 3 was prepared from the reagents and contents indicated in the table below:

[0823] [Tableauxô] Reagents Mass Percentage (%) (relative to the total weight of the alkyd resin obtained) Alkyd Resin 3 63.21 Tert-butyl 1 Acetoacetate 36.79

[0824] In a 250 mL reactor equipped with mechanical stirring and a distillation column, 100 g of the alkyd resin of Example 3.1 and 59.19 g of tert-butyl acetoacetate are introduced. The reaction mixture is heated to 140 °C for 3 hours and then placed under continuous vacuum at 140 °C for 1 hour. An amber-colored polymer is obtained.

[0825] Analysis by 'H NMR spectrometry shows the presence of AcAc groups on the polyester obtained.

[0826] Example 4: Synthesis of a polyester with acetoacetate groups (polyester 4) Example 4.1 Alkyd resin 4 - not part of the invention

[0827] Alkyd resin 4 was prepared from the reagents and contents indicated in the table below:

[0828] [Tables?] Reagents Mass Percentage (%) (relative to the total weight of the akyd resin obtained) Dipentaerythritol 7.41 Pentaerythritol 25.93 Lauric Acid 6.17 Isostearic Acid (Prisefine™ 3505 marketed by CRODA) 37.04 Adipic Acid 14.81 Homophthalic Acid 8.64 Painting?

[0829] a) In a 0.5 L reactor equipped with mechanical stirring, a distillation column, and an argon inlet, 18.74 g of dipentaerythritol, 78.75 g of pentaerythritol, 26.25 g of lauric acid, and 112.50 g of isostearic acid are introduced. The reactor is maintained under an argon atmosphere throughout the bubbling synthesis. The reaction mixture is heated to 230 °C for 7 hours.

[0830] The acid value la is measured: la = 11.30 mg KOH / g.

[0831] b) 37.50 g of adipic acid and 26.25 g of homophthalic acid are introduced into the reactor. The heating is maintained at 230 °C for 7 hours, before cooling.

[0832] Alkyd resin is obtained in the form of a highly viscous, caramel-colored liquid polymer.

[0833] The final acid value and the hydroxyl value IOH are measured.

[0834] la = 4.5 mg KOH / g

[0835] I0H= 267 mg KOH / g. Example 4.2 Polyester 4 - invention

[0836] Polyester 4 was prepared from the reagents and contents indicated in the table below:

[0837] [Tables8] Reagents Mass Percentage (%) (relative to the total weight of the alkyd resin obtained) Alkyd Resin 4 57.01 Tert-butyl acetoacetate 42.99 Table 8

[0838] In a 250 mL reactor equipped with mechanical stirring and a distillation column, 114.02 g of the alkyd resin of Example 4.1 and 85.88 g of tert-butyl acetoacetate are introduced. The reaction mixture is heated to 140 °C for 4 hours and then placed under continuous vacuum at 140 °C for 1 hour. A highly viscous, caramel-colored polymer is obtained.

[0839] Analysis by *H NMR spectrometry shows the presence of AcAc groups on the polyester obtained.

[0840] Example 5: Synthesis of a polyester with acetoacetate groups (polyester 5) Example 5.1 Alkyd resin 5 - not part of the invention

[0841] Alkyd resin 5 was prepared from the reagents and contents indicated in the table below:

[0842] [Tables9] Reagents Mass Percentage (%) (relative to the total weight of the alkyd resin obtained) Dipentaerythritol 32.01 Pripol 2033 (marketed by CRODA) 6.92 Octanoic acid 18.89 Oleic acid 27.70 Adipic acid 8.81 Homophthalic acid 5.67 Table 9

[0843] a) In a 0.5 L reactor equipped with mechanical stirring, a distillation column, and an argon inlet, 128.04 g of dipentaerythritol, 27.68 g of Pripol 2033, 75.56 g of octanoic acid, and 110.8 g of oleic acid are introduced. The reactor is maintained under an argon atmosphere throughout the bubbling synthesis. The reaction mixture is heated to 180 °C for 5 hours.

[0844] b) 35.24 g of adipic acid and 22.68 g of homophthalic acid are introduced into the reactor. Heating is maintained at 230 °C for 8 hours, before cooling.

[0845] Alkyd resin is obtained in the form of a highly viscous, caramel-colored liquid polymer.

[0846] The final acid value and the hydroxyl value IOH are measured.

[0847] la = 2.41 mg KOH / g

[0848] IOH = 232 mg KOH / g Example 5.2 Polyester 5 - invention

[0849] Polyester 5 was prepared from the reagents and contents indicated in the table below:

[0850] [TableauxlO] Reagents Mass Percentage (%) (relative to the total weight of the alkyd resin) Alkyd Resin 5 60.41 Tert-Butylacetoacetate 39.59 Table 10

[0851] In a 250 mL reactor equipped with mechanical stirring and a distillation column, 60.41 g of the alkyd resin of Example 5.1 and 39.59 g of tert-butyl acetoacetate are introduced. The reaction mixture is heated to 140 °C for 3 hours and then placed under continuous vacuum at 140 °C for 1 hour. An amber-colored polymer is obtained.

[0852] Analysis by *H NMR spectrometry shows the presence of AcAc groups on the polyester obtained.

[0853] Example 6: Synthesis of a polyester with acetoacetate groups (polyester 6) Example 6.1 Alkyd resin 6.1 - not part of the invention

[0854] Alkyd resin 6.1 was prepared from the reagents and contents indicated in the table below:

[0855] [Tableauxll] Reagents Mass Percentage (%) (relative to the total weight of the alkyd resin obtained) Oleic Alcohol 50% Decanediol 23.78% Citric Acid 26.22% Table 11

[0856] In a 0.5 L reactor equipped with mechanical stirring, a distillation column, and an argon inlet, 200 g of oleyl alcohol, 95.12 g of 1,10-dedanediol, and 104.88 g of citric acid are introduced. The reaction mixture is gradually heated to 190 °C in 1 hour, then the temperature is maintained at 190 °C for 10 hours, before being raised to 230 °C for 7 hours. The alkyd resin is obtained as a viscous, amber-colored oil.

[0857] The acid value is measured.

[0858] la = 2.78 mg KOH / g Example 6.2 Alkyd resin 6.2 - not part of the invention

[0859] Alkyd resin 6.2 was prepared from the reagents and contents indicated in the table below:

[0860] [Tables 12] Reagents Mass Percentage (%) (relative to the total weight of the alkyd resin obtained) Alkyd resin 6.1 64.10 1-Thioglycerol (3-Mercapto-L2-propanediol) (marketed by Sigma Aldrich under reference 841705) 35.90 Table 12

[0861] In a 250 mL reactor containing 150 mL of ethyl acetate, 25 g of the alkyd resin of Example 6.1, 14 g of 1-thioglycerol, and 2 g of 2-hydroxy-2-methylpropiophenone (commercially available from Sigma Aldrich under reference 405655) are introduced. The reaction mixture is then stirred for 5 minutes under argon gas and subsequently irradiated under a UV lamp (100 W, 365 nm) for 4 hours. The reaction mixture is then washed twice with saturated NaCl water. The organic phase is finally dried over MgSO4 and then concentrated under vacuum. A polymer in the form of a viscous, yellow oil is obtained.

[0862] la = 2.78 mg KOH / g

[0863] Ioh= 279.5 mg KOH / g Example 6.3 Polyester 6 - invention

[0864] Polyester 6 was prepared using the following reagents in the masses and mass percentages indicated:

[0865] [Tables 13] Reagents Mass Percentage (%) (relative to the total weight of the alkyd resin obtained) Alkyd Resin 6.2 55.87 Tert-butyl α-ketoacetate 44.13 Table 13

[0866] In a 250 mL round-bottom flask equipped with a mechanical stirrer, 20 g of the alkyd resin of Example 6.2 and 15.8 g of tert-butyl acetoacetate are introduced. The reaction mixture is heated to 130 °C using an oil bath for 4 hours and then placed under continuous vacuum at 130 °C for 1 hour. A viscous, caramel-colored liquid polymer is obtained.

[0867] Analysis by *H NMR spectrometry shows the presence of AcAc groups on the polyester obtained. Example 7#: Preparing compositions IA and IB

[0868] Composition IA comprising an alkyd resin not of the invention and composition IB comprising a polyester of formula (I) according to the invention are prepared from the contents indicated in the table below. The contents are expressed as a percentage by weight, relative to the total weight of the composition.

[0869] [Tables 14] Compounds Composition 1A (not part of the invention) Composition IB (invention) Alkyd resin 1 25 - Polyester 1 — 25 Red Iron Oxide (CI: 77491, Suapuro Red Iron Oxide C33-SQ01, marketed by Sun) 5 5 Spermidine (CAS: 124-20-9, marketed by Sigma Aldrich) 5 5 Isododecayate (90 / 10) QSP 100 QSP 100 Table 14

[0870] Compositions IA and IB are prepared by mixing the ingredients detailed in Table 14, according to the homogenization protocol specified above.

[0871] Example 8: One-step skin application of compositions IA and IB

[0872] Compositions IA and IB are applied according to the one-step skin application protocol described above.

[0873] The deposits are then evaluated according to the protocols for resistance to olive oil, sebum and water, and to tape of the formulations on Bioskin.

[0874] The evaluation results are summarized in the table below:

[0875] [Tables 15] Properties Scotch tape test Resistance Olive oil Resistance Sebum Resistance Water resistance Composition IA (not part of the invention) 0 0 0 0 Composition IB (invention) +++; 4“h H—?—T" Table 15

[0876] It appears that the application of composition IB according to the process of the invention makes it possible to obtain a very significantly improved resistance to olive oil, water and sebum compared to the application of composition IA, and the tape test is also very effective, thus showing that composition IB adheres to the support.

[0877] We therefore obtain, thanks to the application of composition IB according to the process of the invention, deposits resistant to daily chemical aggressions (water / sebum / olive oil) and very adhesive.

[0878] Moreover, the process according to the invention is particularly advantageous from an environmental point of view, in particular due to the absence of water-based solvent, and therefore the associated water savings, and the small number of steps required to obtain AcAc polyester. Example 9#: Preparation of compositions 2A and 2B

[0879] Composition 2A comprising an alkyd resin not of the invention and composition 2B comprising a polyester of formula (I) according to the invention are prepared from the contents indicated in the table below. The contents are expressed as a percentage by weight, relative to the total weight of the composition.

[0880] [Tableauxlô] Compounds Composition 2A (not part of the invention) Composition 2B (invention) Alkyd resin 1 25 - Polyester 1 - 25 Red Iron Oxide (CI: 77491, Sunpuro Red Iron Oxide C33-80OL marketed by Sun.) 5 5 Titanium butoxide (marketed by Sigma Aldrich) 5 5 Isododecane / Ethanol (90 / 10) QSP 100 QSP 100 Table 16

[0881] Compositions 2A and 2B are prepared by mixing the ingredients detailed in Table 16, according to the homogenization protocol specified above.

[0882] Example 10: One-step skin application of compositions 2A and 2B

[0883] Compositions 2A and 2B are applied according to the one-step skin application protocol described above.

[0884] The deposits are then evaluated according to the protocols for resistance to olive oil and fragmentation of the formulations on Bioskin.

[0885] The evaluation results are summarized in the table below:

[0886] [Tables 17] Properties Fragmentation Resistance Olive oil Composition 2 A (not part of the invention) 0 4- Composition 2 B (invention) _j.__L._L 4-3-4-

[0887] It appears that the application of composition 2B according to the process of the invention makes it possible to obtain a very significantly improved retention of olive oil compared to the application of composition 2A, and the fragmentation test is also very effective, thus showing that the film obtained with composition 2B is very elastic.

[0888] We therefore obtain, by applying composition 2B according to the process of the invention, deposits resistant to oils (olive oil) and very elastic (fragmentation).

[0889] Moreover, the process according to the invention is particularly advantageous from an environmental point of view, in particular due to the absence of water-based solvent, and therefore the associated water savings, and the small number of steps required to obtain AcAc polyester.

[0890] Example 11: Preparation of compositions 3A and 3B

[0891] Composition 3A comprising an alkyd resin not of the invention and composition 3B comprising a polyester of formula (I) according to the invention are prepared from the contents indicated in the table below. The contents are expressed as a percentage by weight, relative to the total weight of the composition.

[0892] [Tables 18] Compounds Composition 3A (not part of the invention) Composition 3B (invention) Alkyd resin 1 25 - Polyester 1 25 Iron Oxide Yellow (Sunpuro Yellow Iran Oxide C33t9001, marketed by Sun) 5 5 Trimethylolpropane triacMate (marketed by Sigma Aldrich) 5 5 1,8-Diazabicyclo[5.4.0]tmdec-7-ene (DBU) 1 1 Isudodecaaate / Ethanol (90 / 100) QSP 100 QSP 100 Table 18

[0893] Compositions 3A and 3B are prepared by mixing the ingredients detailed in Table 18 in the following order: the polyester of formula (I) with acetoacetate functions or the alkyd resin(s) not bearing an acetoacetate function, the pigment, the solvent and the crosslinking agent are homogenized together in the Speedmixer (a mixing equipment which uses centrifugal force) for 2 minutes, at 3,500 rpm and at room temperature, then the catalyst is introduced after the homogenization step.

[0894] Example 1 2: One-step skin application of compositions 3A and 3B

[0895] Compositions 3A and 3B are applied according to the skin application protocol in a step described previously.

[0896] The deposits are then evaluated according to the protocols for resistance to olive oil, sebum and water, and to tape of the formulations on Bioskin.

[0897] The evaluation results are summarized in the table below:

[0898] [Tables 19] Properties Scotch tape test Resistance Olive oil Resistance Sebum Resistance Water resistance Composition 3A 0 0 0 0 Composition 3B —{—!—»_ -W- 4- H—;—1_. T—'—F Table 19

[0899] It appears that the application of composition 3B according to the process of the invention makes it possible to obtain a very significantly improved resistance to olive oil, water and sebum compared to the application of composition 3A, and the tape test is also very effective, thus showing that composition 3B adheres to the support.

[0900] We therefore obtain, thanks to the application of composition 3B according to the process of the invention, deposits resistant to daily chemical aggressions (water / sebum / olive oil) and very adhesive.

[0901] Moreover, the process according to the invention is particularly advantageous from an environmental point of view, in particular due to the absence of water-based solvent, and therefore the associated water savings, and the small number of steps required to obtain AcAc polyester.

[0902] Example 13: Preparation of compositions 4A and 4B

[0903] Composition 4A comprising an alkyd resin not of the invention and composition 4B comprising a polyester of formula (I) according to the invention are prepared from the contents indicated in the table below. The contents are expressed as a percentage by weight, relative to the total weight of the composition.

[0904] [Tables20] Compounds Composition 4A (not part of the invention) Composition 4B (invention) Resin aikvde 1 ■"Ts Polyester 1 - 25 Black Iron Oxide (Stmpuro Black Iron Oxide C33-7O11, marketed by Sun) 5 5 Terephthalide (marketed by Sigma Aldrich) 2.5 2.5 1,8-Diazabicyclo[5.4.0]undec-7 -ene (DBU) 1 1 IsododecaaeÆîhaaol (90 / 10) QSP 100 QSP 100 Table 20

[0905] Compositions 4A and 4B are prepared by mixing the ingredients detailed in Table 20 in the following order: the polyester of formula (I) with functions acetoacetates or alkyd resin(s) not carrying acetoacetate function, pigment, solvent and crosslinking agent are homogenized together in the Speedmixer (a mixing equipment that uses centrifugal force) for 2 minutes, at 3,500 rpm and at room temperature, then the catalyst is introduced after the homogenization step.

[0906] Example 14: One-step skin application of compositions 4A and 4B

[0907] Compositions 4A and 4B are applied, according to the skin application protocol in a step described previously.

[0908] The deposits are then evaluated according to the protocols for resistance to olive oil, sebum and water, and to tape of the formulations on Bioskin.

[0909] The evaluation results are summarized in the table below:

[0910] [Tables21] Properties Scotch tape test Resistance Olive oil Resistance Sebum Resistance Water resistance Composition 4A 0 0 0 0 Composition 4B 4—Hr 4--3--4- -7-+ + +++ Table 21

[0911] It appears that the application of composition 4B according to the process of the invention makes it possible to obtain a very significantly improved resistance to olive oil, water and sebum compared to the application of composition 4A, and the tape test is also very effective, thus showing that composition 4B adheres to the support.

[0912] We therefore obtain, thanks to the application of composition 4B according to the process of the invention, deposits resistant to daily chemical aggressions (water / sebum / olive oil) and very adhesive.

[0913] Moreover, the process according to the invention is particularly advantageous from an environmental point of view, in particular due to the absence of water-based solvent, and therefore the associated water savings, and the small number of steps required to obtain AcAc polyester.

[0914] Example 15: Preparation of compositions 5A and 5B

[0915] Composition 5A comprising an alkyd resin not of the invention and composition 5B comprising a polyester of formula (I) according to the invention are prepared from the contents indicated in the table below. The contents are expressed as a percentage by weight, relative to the total weight of the composition.

[0916] [Tables22] Compounds Composition 5A (not part of the invention) Composition 5B (invention) Alkyd resin 3 80 - Polyester 3 — 80 D&C RED 7 - Calcium salt of Lithol Red B Unipure Red LC-3079 (Sensient) 5 5 (3-Aminopropyl) triethoxysimum (APTES) (CAS No. 919-30-2, marketed by Sigma Aldrich) 10 10 Ethanol QSP 100 QSP 100 Table 22

[0917] Compositions 5A and 5B are prepared by mixing the ingredients detailed in Table 22, according to the homogenization protocol specified above.

[0918] Example 16: One-step skin application of compositions 5A and 5B

[0919] Compositions 5A and 5B are applied according to the one-step skin application protocol described above.

[0920] The deposits are then evaluated according to the protocols for resistance to olive oil, sebum and water, and to tape of the formulations on Bioskin.

[0921] The evaluation results are summarized in the table below:

[0922] [Tables23] Properties of Scotch Tape Test: Resistance to Olive Oil, Resistance to Sebum, Resistance to Water. Composition 5A (not part of the invention): 0 0 0 0. Composition 5B (part of the invention): 4-H-4- -4— —r- -444- Table 23

[0923] It appears that the application of composition 5B according to the process of the invention makes it possible to obtain a very significantly improved resistance to olive oil, water and sebum compared to the application of composition 5A, and the tape test is also very effective, thus showing that composition 5B adheres to the support.

[0924] We therefore obtain, thanks to the application of composition 5B according to the process of the invention, deposits resistant to daily chemical aggressions (water / sebum / olive oil) and very adhesive.

[0925] Moreover, the process according to the invention is particularly advantageous from an environmental point of view, in particular due to the absence of water-based solvent, and therefore the associated water savings, and the small number of steps required to obtain AcAc polyester.

[0926] Example 17: Preparation of compositions 6 A and 6 B

[0927] Composition 6A comprising an alkyd resin not of the invention and composition 6B comprising a polyester of formula (I) according to the invention are prepared from the contents indicated in the table below. The contents are expressed as a percentage by weight, relative to the total weight of the composition.

[0928] [Tables24] Compounds Composition 6A (not part of the invention) Composition 6B (invention) Alkyd resin 4 25 Polyester 4 - 25 Lake Blue 1 - Brilliant Blue Aluminum Lacquer FCP On Alumina (12 / 88) (CI: 42090:2+77002) 5 5 Poly(dimethylsiloxane), bis(3-ammopropyl) terminated (PDMS-diNH2) (CAS No.: 106214-84-0) 6 6 Speroedine (CAS No.: 124-20-9, marketed by Sigma Aldrich) 2 Isododecane / Ethylhexyl (80 / 20) QSP 100 QSP 100 Table 24

[0929] Compositions 6A and 6B are prepared by mixing the ingredients detailed in Table 24, according to the homogenization protocol specified above.

[0930] Example 18: One-step skin application of compositions 6A and 6B

[0931] Compositions 6A and 6B are applied according to the one-step skin application protocol described above.

[0932] The deposits are then evaluated according to the protocols for resistance to olive oil and fragmentation of the formulations on Bioskin.

[0933] The evaluation results are summarized in the table below:

[0934] [Tables25] Properties of the tape test: Oil resistance (Folh-e), Sebum resistance, Water resistance. Composition 6A: 0 0 0 0. Composition 6B: -HH- -rr Ht Table 25

[0935] It appears that the application of composition 6B according to the process of the invention makes it possible to obtain a very significantly improved resistance to olive oil, water and sebum compared to the application of composition 6A, and the tape test is also very effective, thus showing that composition 6B adheres to the support.

[0936] We therefore obtain, thanks to the application of composition 6B according to the process of the invention, deposits resistant to daily chemical aggressions (water / sebum / olive oil) and very adhesive.

[0937] Moreover, the process according to the invention is particularly advantageous from an environmental point of view, in particular due to the absence of water-based solvent, and therefore the associated water savings, and the small number of steps required to obtain AcAc polyester.

[0938] Example 19: P repair of compositions 7A and 7B

[0939] Composition 7A comprising an alkyd resin not related to the invention and composition 7B comprising a polyester of formula (I) according to the invention are prepared from the contents indicated in the table below. The contents are expressed as a percentage by weight, relative to the total weight of the composition.

[0940] [Tables26] Compounds Composition 7A (not part of the invention) Composition 7B (Invention) Alkyd resin 5 25 - Polyester 5 - 25 RED 28 LAKE - Disodium Phloxine B Aluminum Lake on Alumina, Aluminum Beazoate (CI: 45410:2 + 77002) 5 5 4,7,10-Trioxa-L13-tridecanediamiiie (CAS No.: 4246-51-9, marketed by Sigma Aldrich) 5 5 Isododecane / Ethyl alcohol (90 / 10) QSP 100 QSP 100 Table 26

[0941] Compositions 7A and 7B are prepared by mixing the ingredients detailed in Table 26, according to the homogenization protocol specified above.

[0942] Example 20: One-step skin application of compositions 7A and 7B

[0943] Compositions 7A and 7B are applied according to the one-step skin application protocol described above.

[0944] The deposits are then evaluated according to the protocols for resistance to olive oil, sebum and water, and to tape of the formulations on Bioskin.

[0945] The evaluation results are summarized in the table below:

[0946] [Tables27] Properties Scotch tape test Resistance Olive oil Resistance Sebum Resistance vau Composition 7A (not part of the invention) 0 0 0 Q Composition 7B (invention) -i—H- -ii H" “T Table 27

[0947] It appears that the application of composition 7B according to the process of the invention makes it possible to obtain a significantly improved persistence to olive oil, water and sebum compared to the application of composition 7A, and the Scotch tape test is also very effective, thus showing that composition 7B adheres well to the substrate.

[0948] We therefore obtain, thanks to the application of composition 7B according to the process of the invention, deposits resistant to daily chemical aggressions (water / sebum / olive oil) and very adhesive.

[0949] Moreover, the process according to the invention is particularly advantageous from an environmental point of view, in particular due to the absence of water-based solvent, and therefore the associated water savings, and the small number of steps required to obtain AcAc polyester.

[0950] Example 21: P repair of compositions 8A and 8B

[0951] Composition 8A comprising an alkyd resin not related to the invention and composition 8B comprising a polyester of formula (I) according to the invention are prepared from the contents indicated in the table below. The contents are expressed as a percentage by weight, relative to the total weight of the composition.

[0952] [Tables28] Compounds Composition SA (not part of the invention) Composition SB (invention) Alkyd resin 4 25 - Polyester 4 - 25 Black Iron Oxide (Stimuro Black Iron Oxide C33-701L marketed by Sun) 15 15 4J,lÔ-Trioxa-lX3-tridecanediamine OL CAS; 4246-51-9. marketed by Sigma Aldrich) 5 5 Isododecane / Ethanol (90 / 10) QSP 100 QSP 100 Table 2. 8

[0953] Compositions 8A and 8B are prepared by mixing the ingredients detailed in Table 28, according to the homogenization protocol specified above.

[0954] Example 22: One-step skin application of compositions 8A and 8B

[0955] Compositions 8A and 8B are applied according to the one-step skin application protocol described above.

[0956] The deposits are then evaluated according to the protocols for resistance to olive oil, sebum and water of the formulations on Bioskin.

[0957] The evaluation results are summarized in the table below:

[0958] [Tables29] Properties Olive oil resistance Sebum resistance Water resistance Composition 8A 0 0 0 Composition 8B 4-+ H——5— 4-i- Table 29

[0959] It appears that the application of composition 8B according to the process of the invention makes it possible to obtain a very significantly improved persistence to olive oil, water and sebum compared to the application of composition 8A.

[0960] We therefore obtain, thanks to the application of composition 8B according to the process of the invention, deposits resistant to daily chemical aggressions (water / sebum / olive oil).

[0961] Moreover, the process according to the invention is particularly advantageous from an environmental point of view, in particular due to the absence of water-based solvent, and therefore the associated water savings, and the small number of steps required to obtain AcAc polyester.

[0962] Example 23: P repair of compositions 9A and 9B

[0963] Composition 9A comprising an alkyd resin outside the scope of the invention and composition 9B comprising a polyester of formula (I) according to the invention are prepared from the contents indicated in the table below. The contents are expressed as a percentage by weight, relative to the total weight of the composition.

[0964] [Tables 30] Compounds Composition 9A (not an invention) Composition 9B (invention) Base coat Alkyd resin 6.2 20 Polyester 6 20 Yellow Iron Oxide (Sunpuro YeÛow Iron Oxide C33-9OOL marketed by San) 5 5 Isododecane. Ethanol (80 / 20) QSP 100 QSP 100 Top coat [4-6% Mercaptopropylmethylsiloxane]-Dirnethylsilaxane Copplymer (SMS-042, molar mass 6,000-8,000 g / mol, CAS No. 102783-03-9, marketed by Gelest) 2.5 2.5 Spermidine (CAS No. 124-20-9, marketed by Sigma Aldrich) 2.5 2.5 Isododecane Ethanol (50 / 50) QSP 100 QSP 100 Table 30

[0965] Compositions 9A and 9B are prepared by mixing the ingredients detailed in Table 30, according to the homogenization protocol specified above.

[0966] Example 24: Two-step skin application of compositions 9A and 9B

[0967] Compositions 9A and 9B are applied according to the two-step skin application protocol described above.

[0968] The deposits are then evaluated according to the sebum and tape resistance protocols of the formulations on Bioskin.

[0969] The results of the evaluations are summarized in the table below:

[0970] [Tables31] Properties Scotch-Climate Test Resistance Sebum Composition G 0 Composition 9B .4—p 4-4- Table 31

[0971] It appears that the application of composition 9B according to the process of the invention makes it possible to obtain a sebum retention that is very significantly improved compared to the application of composition 9A, and the tape test is also very effective, thus showing that composition 9B adheres to the support.

[0972] Thus, by applying composition 9B according to the process of the invention, we obtain deposits that are resistant to grease (sebum) and very adhesive.

[0973] Moreover, the process according to the invention is particularly advantageous from an environmental point of view, in particular due to the absence of water-based solvent, and therefore the associated water savings, and the small number of steps required to obtain AcAc polyester.

[0974] Example 25: Preparation of compositions 10A and 10B

[0975] Composition 10A comprising an alkyd resin not of the invention and composition 10B comprising a polyester of formula (I) according to the invention are prepared from the contents indicated in the table below. The contents are expressed as a percentage by weight, relative to the total weight of the composition.

[0976] [Tables32] Compounds Composition 10A (not part of the invention) Composition 10B (invention) Alkyd resin 3 65 Polyester 3 — 65 D&C RED 7 - Calcium Salt of Lithol Red B Uni-pure Red LC 3079 (Seasient) 5 5 (3-Ammopropyl) triethoxysilane (APTES) (CAS No.: 919-30-2, marketed by Sigma Aldrich) 7 Octyl'L2-dodecanol 20 20 Ethanol QSP 100 QSP 100 Table 32

[0977] Compositions 10A and 10B are prepared by mixing the ingredients detailed in Table 32, according to the homogenization protocol specified above.

[0978] Example 26: One-step skin application of compositions 10A and 10B

[0979] Compositions 10A and 10B are applied according to the one-step skin application protocol described above.

[0980] The deposits are then evaluated according to the protocols for resistance to olive oil, sebum and water, and to tape of the formulations on Bioskin.

[0981] The evaluation results are summarized in the table below:

[0982] [Tables33] Properties SCOtcli Test Olive Oil Resistance Sebum Resistance Water Resistance Composition 10 A (not part of the invention) 0 0 0 0 Composition 10 B (invention) -r—rT _i— H—4“ Table 33

[0983] It appears that the application of composition 10B according to the process of the invention makes it possible to obtain a very significantly improved resistance to olive oil, water and sebum compared to the application of composition 10A, and the tape test is also very effective, thus showing that composition 10B adheres to the support.

[0984] We therefore obtain, thanks to the application of composition 10B according to the process of the invention, deposits resistant to daily chemical aggressions (water / sebum / olive oil) and very adhesive.

[0985] Moreover, the process according to the invention is particularly advantageous from an environmental point of view, in particular due to the absence of water-based solvent, and therefore the associated water savings, and the small number of steps required to obtain AcAc polyester.

[0986] Example 27: Preparation of compositions 11A and 11B

[0987] Composition 11A comprising an alkyd resin not related to the invention and composition 1 IB comprising a polyester of formula (I) according to the invention are prepared from the contents indicated in the table below. The contents are expressed as a percentage by weight, relative to the total weight of the composition.

[0988] [Tables34] Compounds Composition 11A (not part of the invention) Composition 11B (invention) Alkyd resin 3 65 - Polyester 3 - 65 D&C RED 7 - Calcium salt of Lithol Red B Unipure Red LC 3079 (Sensient) 5 5 (3-Aminopropyl) triethoxysilane (APTES) (CAS No.: 919-30-2, marketed by Sigma Aidrich) 7 7 Isononanoate of Isononol 20. 20 Ethanol QSP 100 QSP 100 Table 34

[0989] Compositions 11A and 1 IB are prepared by mixing the ingredients detailed in Table 34, according to the homogenization protocol specified above.

[0990] Example 28: One-step skin application of compositions 11A and 11B

[0991] Compositions 1 IA and 1 IB are applied according to the one-step skin application protocol described above.

[0992] The deposits are then evaluated according to the protocols for resistance to olive oil, sebum and water, and to tape of the formulations on Bioskin.

[0993] The evaluation results are summarized in the table below:

[0994] [Tables35] Properties of the Scotch tape test: Resistance to olive oil, resistance to sebum, resistance to water. Composition 11A (not part of the invention): 0 0 0 0. Composition 11B (part of the invention): -4-4 4-4 4-+4- Table 35

[0995] It appears that the application of composition 1 IB according to the process of the invention makes it possible to obtain a very significantly improved resistance to olive oil, water and sebum compared to the application of composition 1 IA, and the tape test is also very effective, thus showing that composition 1 IB adheres to the support.

[0996] We therefore obtain, thanks to the application of composition 1 IB according to the process of the invention, deposits resistant to daily chemical aggressions (water / sebum / olive oil) and very adhesive.

[0997] Moreover, the process according to the invention is particularly advantageous from an environmental point of view, in particular due to the absence of water-based solvent, and therefore the associated water savings, and the small number of steps required to obtain AcAc polyester.

[0998] Example 29: Preparation of compositions 12A1, 12A2, 12B1 and 12B2

[0999] Compositions 12A1, 12A2, 12B1 and 12B2 are prepared from the contents indicated in the table below. The contents are expressed as a percentage by weight, relative to the total weight of the composition in question.

[1000] [Tables 36] Compounds Composition 12A1 (not part of the invention) Composition 12B1 (invention) Composition 12A2 (not part of the invention) Composition 12B2 (invention) Alkyd resin 2 (not part of the invention) 20 20 - Polyester 2 (invention) - 20 - 20 Titanium butoxide — - 5 5 Isodcecane / Bethanol (90 Z10) QSP 100 QSP 100 QSP 100 QSP 100 Table 36

[1001] Compositions 12A1, 12A2, 12B1 and 12B2 are prepared by mixing the ingredients detailed in Table 36, according to the homogenization protocol specified above.

[1002] Example 30: One-step skin application of compositions 12A1, 12A2, 12B1 and 12B2 - Evaluation of the afterglow of brightness

[1003] Compositions 12A1, 12A2, 12B1 and 12B2 and titanium butoxide are applied according to the gloss afterglow protocol described above.

[1004] The values ​​are expressed in UB (Brightness Unit). The evaluation results are summarized in the table below:

[1005] [Tables 37] Contrast card gloss Gloss after 24 hours Gloss after water application and rubbing Composition 12A1 (not part of the invention) 45.2 70.42 24.32 Composition 12B1 (invention) 45.2 76.36 37.58 Composition 12A2 (not part of the invention) 45.2 72.94 65.92 Composition 12B2 (invention) 45.2 79.7 73.88 Titanium butoxide 45.2 N / A ■ N / A Table 37

[1006] It appears that the application of compositions 12B1 and 12B2 according to the process of the invention makes it possible to obtain a film exhibiting high gloss. Furthermore, it appears that the application of compositions 12B1 and 12B2 according to the process of the invention makes it possible to significantly improve the gloss retention after exposure to water.

[1007] Moreover, the process according to the invention is particularly advantageous from an environmental point of view, in particular because of the absence of water-based solvent, and therefore the associated water savings, and the small number of steps required to obtain AcAc polyester.

[1008] Example 31: Preparation of compositions 12A3 and 12B3

[1009] Compositions 12A3 and 12B3 are prepared from the contents indicated in the table below. The contents are expressed as a percentage by weight, relative to the total weight of the composition in question.

[1010] [Tables 38] Compounds Composition 12 A3 (not part of the invention) Composition 12B3 (invention) Alkyd resin 2 (not part of the invention) 20 Polyester 2 (invention) - 20 Titanium butoxide 5 5 Red Iron Oxide (CI: 77491, Sunpuro Red Iron Oxide C33-8001, marketed by Sun) 2 7 Isodine & Ethano 1 (90 / 10) QSP 100 QSP 100 Table 38

[1011] Compositions 12A3 and 12B3 are prepared by mixing the ingredients detailed in Table 38, according to the homogenization protocol specified above.

[1012] Example 32: One-step skin application of compositions 12A3 and 12B3 - Evaluation of the afterglow of brightness

[1013] Compositions 12A3 and 12B3 are applied according to the gloss afterglow protocol described above.

[1014] The values ​​are expressed in UB (Brightness Unit). The evaluation results are summarized in the table below:

[1015] [Tables 39] Contrast card gloss Gloss after 24 hours Gloss after water application and rubbing Composition 12A3 (not part of the invention) 45.2 46.86 46.40 Composition 12B3 (invention) 45.2 73.8' 73.70 Table 39

[1016] It appears that applying composition 12B3 according to the process of the invention produces a film with a high gloss. Furthermore, it appears that applying composition 12B3 according to the process of the invention significantly improves the gloss retention after exposure to water.

[1017] Moreover, the process according to the invention is particularly advantageous from an environmental point of view, in particular because of the absence of water-based solvent, and therefore the associated water savings, and the small number of steps required to obtain AcAc polyester. Example 33#: Preparing Composition 13

[1018] Composition 13 is prepared from the contents indicated in the table below. The contents are expressed as a percentage by weight, relative to the total weight of the composition.

[1019] [Tables 40] Composition 13 (invention) Polyester 2 20 Red Iron Oxide (CI: 77491, Suppura Red. Iran Oxide C33-800I, marketed by Sun) 6 Polyheramine (Jeffamine T403, marketed by Huntsman) 6 Isododecane / Ethanol (90 / 10) QSP 100 Table 40

[1020] Composition 13 is prepared by mixing the ingredients detailed in Table 40, according to the hair colour application protocol specified above.

[1021] Example 34: One-step hair coloring application of composition 13

[1022] Composition 13 is applied according to the one-step capillary application protocol described above. The evaluation results are summarized in the table below:

[1023] [Tables41] Composition Number of shampoos L* a* b* AE Composition 13 (invention) Control 60.79 0.15 11.27 - 0 34.9 21.28 15.22 - 3 34.7 19.63 14.15 1.97 Table 41

[1024] The hair strands colored according to the invention have an AE value of less than 2 after 3 shampoos. It therefore appears that the application of composition 13 according to the process of the invention makes it possible to obtain very good colonic retention.

[1025] Moreover, the process according to the invention is particularly advantageous from an environmental point of view, in particular because of the absence of water-based solvent, and therefore the associated water savings, and the small number of steps required to obtain AcAc polyester. Example 35#: Preparing Composition 14

[1026] Composition 14 is prepared from the contents indicated in the table below. The contents are expressed as a percentage by weight, relative to the total weight of the composition.

[1027] [Tables42] Composition of Compounds 14 (invention) Polyester 3 25 Yellow Iron Oxide (CI: 77492, Simnro Yellow Iron Oxide 03-9001, marketed by Sim) 3 (3-Aminopropyl)triethoxysilane (APTES) (CAS No: 919-30-2, marketed by Sigma Aldrich) 7 Spermidine (CAS No: 124-20-9, marketed by Sigma Aldrich) 3 Ethanol QSP 100 Table 42

[1028] Composition 14 is prepared by mixing the ingredients detailed in Table 42, according to the hair colour application protocol specified above.

[1029] Example 36: One-step hair coloring application of composition 14

[1030] Composition 14 is applied according to the one-step capillary application protocol described above. The evaluation results are summarized in the table below:

[1031] [Tables43] Composition Number of shampoos L* a* LC AE Composition 14 (invention) Control 60.79 0.15 11.27 0 52.91 12.87 38.95 3 52.5 12.12 36.93 2.19 Table 43

[1032] The hair strands colored according to the invention have an AE value of 2.19 after 3 shampoos. It therefore appears that the application of composition 14 according to the process of the invention makes it possible to obtain very good colonic retention.

[1033] Moreover, the process according to the invention is particularly advantageous from an environmental point of view, in particular because of the absence of water-based solvent, and therefore the associated water savings, and the small number of steps required to obtain AcAc polyester. Example 36#: Preparing Composition 15

[1034] Composition 15 is prepared from the contents indicated in the table below. The contents are expressed as a percentage by weight, relative to the total weight of the composition in question.

[1035] [Tables44] Composition 15 (invention) Base coat Polyester 1 25 Red Iron Oxide (CI: 77491, Sunpuio Red Iron Oxide C33-800L marketed by Sun) γ βδδενα β ... Table 44

[1036] Composition 15 is prepared by mixing the ingredients detailed in Table 44, according to the hair colour application protocol specified above.

[1037] Example 3.7: Two-step hair coloring application of composition 15

[1038] Composition 15 is applied according to the two-step capillary application protocol described above.

[1039] The evaluation results are summarized in the table below:

[1040] [Tables45] Composition Number of shampoos I * a* b* AE Composition 15 (invention) Control 60.79 0.15 11.27 0 31.69 27.69 21.07 — 3 34.07 28.57 22.14 0.68 Table 45

[1041] The hair strands colored according to the invention have an AE value of less than 2 after 3 shampoos. It therefore appears that the application of composition 15 according to the process of the invention makes it possible to obtain very good colonic retention.

[1042] Moreover, the process according to the invention is particularly advantageous from an environmental point of view, in particular because of the small number of steps required to obtain AcAc polyester. Example 38#: Preparing Composition 16

[1043] Composition 16 is prepared from the contents indicated in the table below. The contents are expressed as a percentage by weight, relative to the total weight of the composition in question.

[1044] [Tables46] Composition 16 (invention) Base coat Polyester 1 20 Red Iron Oxide (CI: 77491, Simmo Red Iron Oxide C3 3-800 L marketed by Sim) 6 [4-6% Mercaptopropyl]-dimethylsiloxane Copolymer (SMS-042, molar mass 6000-8000 g / mol CAS No: 102783-03-9, marketed by Gelest) Isododecane / Isododecane (90 / 10) QSP 100 Top coat 4,7.10-Trioxa-Isododecane (CAS No: 4246-51-9, marketed by Sigma Aldrich) 5 Water QSP 100 Table 46

[1045] Composition 16 is prepared by mixing the ingredients detailed in Table 46, according to the hair colour application protocol specified above.

[1046] Example 39: 2-step hair coloring application of composition 16

[1047] Composition 16 is applied according to the two-step capillary application protocol described above.

[1048] The evaluation results are summarized in the table below:

[1049] [Tables47] Composition Number of shampoos L* a* b* AE Composition 16 (invention) Control 60.79 0.15 11.27 0 33.29 27.86 21.45 - 3 34.92 26.83 20.92 1.95 Table 47

[1050] The hair strands colored according to the invention have an AE value of less than 2 after 3 shampoos. It therefore appears that the application of composition 16 according to the process of the invention makes it possible to obtain very good colonic retention.

[1051] Moreover, the process according to the invention is particularly advantageous from an environmental point of view, in particular because of the small number of steps required to obtain AcAc polyester. Example 40#: Preparing Composition 17

[1052] Composition 17 is prepared from the contents indicated in the table below. The contents are expressed as a percentage by weight, relative to the total weight of the composition in question.

[1053] [Tables48] Composition 17 (invention) 1. Coat Polyester 2. Red Iron Oxide (CI 7749 L Sunpuro Red Iron Oxide C33-8001, marketed by Sun) 6. Isododecane 1. Ethanol 1. QSP 100 7. Top Coat 1. Polyethylene oxide (Jefiamine 1403, marketed by Huntsman) 9. Water QSP 100 Table 48

[1054] Composition 17 is prepared by mixing the ingredients detailed in Table 48, according to the hair colour application protocol specified above.

[1055] Example 41: Two-step hair coloring application of composition 17

[1056] Composition 17 is applied according to the two-step capillary application protocol described above.

[1057] The evaluation results are summarized in the table below:

[1058] [Tables49] Composition Number of shampoos L* ;r IC AE Composition 17 (invention) Control 60.79 0.15 11.27 0 31.33 27.17 20.37 3 31.82 25.99 18.92 1.93 Table 49

[1059] The hair strands colored according to the invention have an AE value of less than 2 after 3 shampoos. It therefore appears that the application of composition 17 according to the process of the invention makes it possible to obtain very good colonic retention.

[1060] Moreover, the process according to the invention is particularly advantageous from an environmental point of view, in particular because of the small number of steps required to obtain AcAc polyester. Example 42#: Preparing Composition 18

[1061] Composition 18 is prepared from the contents indicated in the table below. The contents are expressed as a percentage by weight, relative to the total weight of the composition in question.

[1062] [Tables 50] Composition 18 (invention) Base coat Polyester 4 20 Red Iron Oxide (CI: 77491, Smipuro Red Iron Oxide C33-8OOL, marketed by Sim) 6 Isododecane / Ethanol (90 / 10) QSP 100 Top coat Spermidine (CAS: 124-2(5-9), marketed by Sigma Aldrich) 2.5 [4-6% Mercaptopropyl]methylsilox - Dimethylkiloxane Copolymer (SMS-042, molar mass 6,000-8,000 g / mol, CAS No.: 102783-03-9, marketed by Gelest) 2.5 Isododecane / Ethanol (90 / 10) QSP 100 Table 50

[1063] Composition 18 is prepared by mixing the ingredients detailed in Table 50, according to the hair colouring application protocol specified above.

[1064] Example 43: Two-step hair coloring application of composition 1 8

[1065] Composition 18 is applied according to the two-step capillary application protocol described above.

[1066] The evaluation results are summarized in the table below:

[1067] [Tables 51] Composition Number of shampoos T* a* b* AE Composition 18 (invention) Control 60.79 0.15 11.27 « 0 30.48 25.34 18.15 3 28.98 25.14 18.06 1.51 Tabka» 51

[1068] The hair strands colored according to the invention have an AE value of less than 2 after 3 shampoos. It therefore appears that the application of composition 18 according to the process of the invention makes it possible to obtain very good colonic retention.

[1069] Moreover, the process according to the invention is particularly advantageous from an environmental point of view, in particular because of the absence of water-based solvent, and therefore the associated water savings, and the small number of steps required to obtain AcAc polyester. Example 44#: Preparing Composition 19

[1070] Composition 19 is prepared from the contents indicated in the table below. The contents are expressed as a percentage by weight, relative to the total weight of the composition in question.

[1071] [Tables 52] Composition 19 (invention) Base coat Polyester 4 20 Red Iron Oxide (CF: 77491, Suppuro Red Iron Oxide C33-8OO1, marketed by Sun) 6 Isododecane / Ethanol (90 / 10) QSP 100 Top coat Chitosauce - Poly(D-Gktcosamine) (Kiomitrime CSG, marketed by Kytozyme) 5 Lactic acid 1.9 Water QSP 100 Table 52

[1072] Composition 19 is prepared by mixing the ingredients detailed in Table 52, according to the hair colour application protocol specified above.

[1073] Example 4 5: Two-step hair coloring application of composition 1 9

[1074] Composition 19 is applied according to the two-step capillary application protocol described above.

[1075] The evaluation results are summarized in the table below:

[1076] [Tables 53] Composition Number of shampoos LA a* IC AE Composition 19 (invention) Control 60.79 0.15 11.27 0 32.51 28.8 21.49 3 33.01 27.6 20.24 1.80 Table 53

[1077] The hair strands colored according to the invention have an AE value of less than 2 after 3 shampoos. It therefore appears that the application of composition 19 according to the process of the invention makes it possible to obtain very good colonic retention.

[1078] Moreover, the process according to the invention is particularly advantageous from an environmental point of view, in particular because of the small number of steps required to obtain AcAc polyester. Example 46#: Preparing Composition 20

[1079] Composition 20 is prepared from the contents indicated in the table below. The contents are expressed as a percentage by weight, relative to the total weight of the composition in question.

[1080] [Tables54] Composition of Compounds 20 (invention) 1st step Black Iron Oxide (Sunpuro Black Iron Oxide C33-7011, marketed by Sun) 6 4,7J0-Trioxa-1,13-tridecanediamine (CAS No.: 4246-51-9, marketed by Sigma Aldrich) 2 Water QSP 100 2nd step Polyester 1 20 Isododecane / Ethanol (90 / 10) QSP 100 3rd step Bis-Cetearyl Amodimethicone (marketed by Momentive Performance Materials) 5 Isododecane QSP 100 Tabieaa 54

[1081] Composition 20 is prepared by mixing the ingredients detailed in Table 54, according to the hair colour application protocol specified above.

[1082] Example 4.7: 3-step hair coloring application of composition 20

[1083] Composition 20 is applied according to the three-step capillary application protocol described above.

[1084] The evaluation results are summarized in the table below:

[1085] [Tables 55] Composition Number of shampoos L* a* h AE Composition 20 (invention) Control 60.79 0.15 11.27 - 0 25.06 0.37 0.81 - 3 26.49 0.5 1.78 1.64 Tabiean 55

[1086] The hair strands colored according to the invention have an AE value of less than 2 after 3 shampoos. It therefore appears that the application of composition 20 according to the process of the invention makes it possible to obtain very good colonic retention.

[1087] Moreover, the process according to the invention is particularly advantageous from an environmental point of view, in particular because of the small number of steps required to obtain AcAc polyester.

[1088] Example 48: Preparation of compositions 21A, 21A1, 21A2, 21B, 21B1 and 21B2

[1089] Compositions 21A, 21A1, 21A2, 21B, 21B1 and 21B2 are prepared from the contents indicated in the table below. The contents are expressed as a percentage by weight, relative to the total weight of the composition in question.

[1090] [Tables56] Compounds Composition 21A (invention) Composition 21A1 (comparative) Composition 21A2 (comparative) Composition 21B (invention) Composition 21B1 (comparative) Composition 21B2 (comparative) Polyester 1 20 20 - - - - Polyester 2 - - 20 20 Red Iron Oxide (CI: 77491, Sunpuro Red Iron Oxide C33-8001, marketed by Sun) 6 6 6 " ■ - Polyetheramine (Jeffamine T403, marketed by Huntsman Mw=440g / mol AHEW 81 g / eq) 6.8 6.8 (3-Aminopropyl)triethoxysilane (APTES.) (CAS: 919-30-2, marketed by Sigma Aldrieh) - - 6.4 - 6.4 [4-6% Mercaptopropyi)methylsiioxane] -Dimethylsiioxane Copolymer (SMS-042, molar mass 6,000-8,000 g / mol, CAS No.: 102783-03-9, marketed by Gelest) - - 1.6 - 1.6 Isododecance Zethanol (90 / 10) Qsp 100 Qsp 100 Qsp 100 Qsp 100 Qsp 100 Qsp 100 Table 56

[1091] Compositions 21A, 21A1, 21A2, 21B, 21B1 and 21B2 are prepared by mixing the ingredients detailed in Table 56, according to the Steampod protocol specified above.

[1092] Example 49: One-step hair colouring application of compositions 21A, 21A1, 21A2, 21B, 21B1 and 21B2

[1093] Compositions 21A, 21A1, 21A2, 21B, 21B1 and 21B2 are applied according to the Steampod protocol described above. The evaluation results are summarized in the table below:

[1094] [Tables 57] Composition Number of shampoos IA a* b* AE - Control 60.79 0.15 11.27 - Composition 21A (invention) 0 39.51 22.86 16.19 3 36.81 24.17 18.04 3.52 Composition 21A1 (comparative) 0 34.44 27.24 20.08 - 3 57.5 9.29 16.7 29.41 Composition 21A2 (comparative) 0 35.88 26.17 20.59 3 5.8.55 6.53 14.9 30.52 Composition 21B (invention) 0 36.17 03 17.15 - 3 36.75 ■77 15 16.23 1.89 Composition 21B1 (comparative) 0 34.79 27.06 19.38 — 43.09 24.77 21.39 8.84 Composition 21B2 (comparative) 0 34.16 23.05 16.25 - 3 51.97 14.37 16.99 19.82 Table 57

[1095] Hair strands colored with compositions 21A and 21B according to the invention exhibit lower AE values ​​than hair strands colored with the comparative compositions 21A1, 21A2 and 21B1 and 21B2.

[1096] Thus, the composition according to the invention and the process according to the invention make it possible to obtain a homogeneous coloured coating on the hair with improved persistence to shampoos.

[1097] Moreover, the process according to the invention is particularly advantageous from an environmental point of view, in particular because of the absence of water-based solvent, and therefore the associated water savings, and the small number of steps required to obtain AcAc polyester.

[1098] Example 50: Preparation of formulas 22A, 22B, 22C, 22D, 22E, 22F, 22G, 22H, 221, 22J

[1099] Formulas 22A to 22J are prepared from the contents indicated in the table below. The contents are expressed as a percentage by weight, relative to the total weight of the composition in question.

[1100] [Tables58] Compounds Formula 22 A (comparative) Formula 22B (invention) Formula 22C (comparative) Formula 22D (invention) Formula 22E (comparative) Formula 22F (invention) Formula 22G (comparative) Formula 22H (invention) Formula 221 (comparative) Formula 22 J (comparative) Alkyd resin 1 10 - 5 - - - - - - - Polyester 1 - 10 - - - - - - - Alkyd resin 2 - - 10 5 - - Polyester 2 - - - - 10 - 5 - - Polyetheramine (Jeffamme T403, marketed by Hunismaa) - - 5 5 - 5 5 10 - Isododecane / Ethanal (90 / 10) Qsp 100 Qsp 100 Qsp 100 Qsp 100 Qsp 100 Qsp 100 Qsp 100 Qsp 100 Qsp 100 100 Table 58

[1101] Compositions 22A, 22B, 22C, 22D, 22E, 22F, 22G, 22H, 221 and 22J are prepared by mixing the ingredients detailed in Table 58, according to the styling evaluation protocol specified above.

[1102] Example 51: _ Styling application of compositions G to 0 - Loop evaluation

[1103] Compositions 22A to 22J are applied according to the styling protocol described above.

[1104] The results of the loop evaluations are summarized in the table below:

[1105] [Tables 59] Composition Value after application (cm) Length after application Value after 24h suspension (cm) Length before-after suspension Untreated wick 20.5 - - .NIA Composition 22A. (excluding invention) 16.5 4 18 1.5 Composition 22B (invention) 14 6.5 16.5 2.5 Composition 22C (excluding invention) 6.5 14 il 4.5 Composition 22D (invention) 4 16 6 2 Composition 22E (excluding invention) 14 6.5 16.5 2 Composition 22F (invention) 12 8.5 14 2 Composition 22G (excluding invention) 5 15.5 12 7 Composition 22H (invention) 4 16.5 5.5 1.5 Composition 221 (excluding invention) 17 3.5 19 2 Composition 22 J (excluding invention) 12 8.5 16 4 Table 59

[1106] It appears that strands treated with formulas 22B, 22D, 22F, and 22H according to the process of the invention produce well-formed and well-defined curls and significantly improve the retention of the curl shape over time. In particular, the strands treated according to the process of the invention have a significantly reduced length after application of formulas 22B, 22D, 22F, and 22H compared to the length of strands treated with comparative formulas 22A, 22C, 22E, 22G, 221, and 22J. Thus, the shape of the curls in strands treated according to the process of the invention appears sharper and closer together than in strands treated with comparative compositions 22A, 22C, 22E, 22G, 221, and 22J.

[1107] Furthermore, even after 24 hours, the strands treated with formulas 22B, 22D, 22F and 22H according to the process of the invention have a sharper and cl...

Claims

Demands

1. A process for treating, in particular for cosmetic purposes, keratinous materials, comprising applying to said keratinous materials, in one or more successive steps, at least: i) at least one polyester of the following formula (I) comprising at least two acetoacetate functions, as well as its optical, geometric and / or solvated isomers, such as hydrates, or a composition containing it or them: (Z)-[OC(O)-C(Ra)(Rb)-C(O)-R4]u (I) formula (I) in which: - Z designates a multivalent radical derived from: an alkyd resin (A) obtained by reaction of: - 10% to 62% by mass of at least one polyol; - 10% to 62% by mass of at least one polyacid; - 35% to 60% by mass of at least one fatty alcohol and / or at least one mono-fatty acid; and - from 0% to 20% mass of at least one monocarboxylic acid; the mass percentages being expressed in relation to the total weight of the alkyd resin (A);or of an alkyd resin (B) resulting from the reaction of an alkyd resin (A) containing ethylenic unsaturations with at least one (poly)hydroxy thiol; - u is an integer greater than 2; - R4 represents a monovalent hydrocarbon radical in the C1 to C6 group, linear or branched, saturated or unsaturated, preferably a (C1-C4)alkyl group, in particular methyl or tert-butyl, more preferably methyl; - Ra and Rb, identical or different, represent a hydrogen atom or a (CrC4)alkyl group, preferably a hydrogen atom; and ii) optionally, at least one crosslinking agent.

2. A treatment method according to the preceding claim, wherein (Z) represents a multivalent radical comprising from 40 to 6000 carbon atoms, terminated by m -O- radicals and n -C(O)ORz radicals, with: - m an integer greater than 2, preferably greater than or equal to 10, - n an integer greater than or equal to zero, - Rz a hydrogen atom or an alkyl group comprising from 4 to 40 atoms, in particular from 5 to 32 atoms, and more preferably from 6 to 24 carbon atoms, said multivalent radical being cyclic or acyclic, branched, saturated or unsaturated, interrupted by several ester radicals -OC(O)- or -C(O)-O-, and possibly interrupted by one or more non-adjacent sulfur atoms S.

3. A treatment method according to any one of the preceding claims, wherein the -C(O)ORz radical(s) is / are selected from t-butyl esters, oleyl esters, caprylic acid esters, 2-ethylhexanoic acid esters, 4,5-dimethylhexanoic acid esters, 2-heptylheptanoic acid esters, 3,5,5-trimethylhexanoic acid esters, octanoic acid, isooctanoic acid, nonanoic acid, decanoic acid, isononanoic acid, lauric acid, tridecanoic acid, myristic acid, palmitic acid, stearic acid, isostearic acid, arachidic acid, behenic acid, cerotic (hexacosanoic) acid, and other similar acids. 3-cyclopentylpropionic acid, 3-cyclohexylpropionic acid, cyclohexylacetic acid, 4-cyclohexylbutyric acid, caproleic acid, undecylenic acid, dodecylenic acid, myristoleic acid, palmitoleic acid, oleic acid, linoleic acid, linolenic acid, elaidic acid, gondoic acid,of erucic acid.

4. A treatment method according to any one of the preceding claims, comprising applying to said keratinous materials, preferably skin and / or hair, at least ii) a crosslinking agent, in particular selected from polyamine, polythiol, polycarbonyl, polyacrylate, metal alkoxide, amino alkoxysilanes comprising only one primary and / or secondary amine group, and mixtures thereof, optionally in association with an amine catalyst, in particular selected from piperidine, DMAP (dimethylaminopyridine), DBU (1,8-diazabicyclo[5.4.0]undec-7-ene), DABCO (1,4-diazabicyclo[2.2.2]octane), DBN (1,5-diazabicyclo[4.3.0]non-5-ene), more preferably selected from DBU (1,8-diazabicyclo[5.4.0]undec-7-ene), DABCO (1,4-diazabicyclo[2.2.2]octane), DBN (1,5-Diazabicyclo[4.3.0]non-5-ene), and in particular the catalyst is DBU (1,8-Diazabicyclo[5.4.0]undec-7-ene); more preferably at least one crosslinking agent is chosen from spermidine, titanium butoxide (Ti(OCH2CH2CH2CH3)4), trimethylolpropane triacrylate, terephthalaldehyde, (3-aminopropyl)triethoxysilane (APTES), polydimethylsiloxanes comprising primary amine groups at the end of the chain or on side chains, such as Bis-Cetearyl Amodimethicone, 4,7,10-trioxa-l,13-tridecanediamine, polydimethylsiloxanes comprising at least two thiol groups, triamine polyethers, in particular polyetheramines (or jeffamine), chitosans (in particular poly(D-glucosamine)), and mixtures thereof.

5. A method according to any one of the preceding claims, further comprising the application to said keratinous materials, preferably skin and / or hair, of at least iv) a cosmetic active, preferably cosmetic active(s) iv) being selected from: a) coloring materials, in particular selected from pigments, direct dyes and mixtures thereof, b) conditioning agents for keratinous materials, preferably skin and / or hair, c) UV filters, and d) mixtures thereof;preferably the cosmetic active ingredient(s) iv) are chosen from a) colouring materials, preferably chosen from pigments, direct colorants and their mixtures, more preferably the pigment(s) are chosen from carbon black, iron oxides, in particular yellow, red and black and iron oxide coated micas, triarylmethane pigments, in particular blue and violet, in particular BLUE 1 LAKE, azo pigments, in particular red, more particularly D&C RED 7, the alkali metal salt of lithol red, in particular the calcium salt of lithol red B, and even more preferably from red iron oxides, yellow iron oxides and azo pigments, in particular red, more particularly D&C RED 7.;

6. A method according to any one of the preceding claims, further comprising applying to said keratinous materials, preferably skin and / or hair, at least (v) a fatty substance, in particular at least one oil, in particular selected from: (a) volatile oils, in particular selected from: - hydrocarbon oils having 8 to 16 carbon atoms, in particular C8-Ci6 branched alkanes, in particular isoalkanes, more particularly iso-alkanes (also called isoparaffins), preferably Ci3-Ci6 isoparaffin, isododecane, isodecane, isohexadecane, 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), linear alkanes, in particular Cn-Cl6, alone or in mixtures, in particular hexane, decane, undecane, tridecane,isoparaffins in particular n-dodecane (Ci2) and n-tetradecane (CM), the undecane-tridecane mixture, mixtures of n-undecane (Cn) and n-tridecane (Cn), and their mixtures as well as mixtures of n-undecane (Cn) and n-tridecane (Ci3), and volatile non-aromatic cyclic alkanes in C5-Ci2; - short-chain esters having from 3 to 8 carbon atoms in total, in particular ethyl acetate, methyl acetate, propyl acetate, n-butyl acetate; - Carbonate hydrocarbon oils of structure R'i-OC(O)-O-R'2 in which R'i and R'2 independently designate a linear, branched or cyclic C4-C8 alkyl group, preferably a C4-C8 alkyl group, more preferably chosen from dibutyl carbonate or dipentyl carbonate; - Ether oils of formula RrO-R2, in which Ri and R2 independently designate a linear, branched or cyclic C4-C8 alkyl group,preferably an alkyl group in C4-C8; - silicone oils, in particular comprising 2 to 7 silicon atoms, and possibly containing alkyl or alkoxy groups having 1 to 10 carbon atoms, in particular dimethicones with viscosities of 5 and 6 cSt, cyclopentadimethylsiloxane, dodecamethylpentasiloxane, cyclohexadimethylsiloxane, octamethyl cyclotetrasiloxane, decamethyl cyclopentasiloxane, dodecamethyl cyclohexasiloxane, heptamethyl hexyltrisiloxane, heptamethyloctyl trisiloxane, hexamethyl disiloxane, octamethyl trisiloxane, decamethyl tetrasiloxane, dodecamethyl pentasiloxane, and mixtures thereof; or b) non-volatile oils, in particular selected from: - non-volatile fluorinated oils, in particular selected from fluorinated polyethers, fluorosilicone oils, fluorinated silicones; - non-volatile silicone oils, in particular selected from non-volatile silicones with the following INCI names: dimethicone, dimethiconol, trimethyl pentaphenyl trisiloxane, tetramethyl tetraphenyl trisiloxane, diphenyl dimethicone, trimethylsiloxyphenyl dimethicone, phenyltrimethicone, diphenylsiloxy phenyl trimethicone, and mixtures thereof; - non-volatile non-polar hydrocarbon oils, in particular chosen from linear or branched compounds, of mineral or synthetic origin: paraffin oil, squalane, isoeicosane, mixtures of linear, saturated hydrocarbons, more particularly in C15-C28, in particular mixtures whose INCI names are (Ci5-Ci9)alkane, (Ci8-C2i)alkane, (C2i-C28)alkane, polybutenes, hydrogenated or not; polyisobutenes, hydrogenated or not, preferably hydrogenated, polydecenes, hydrogenated or not, decene / butene copolymers, butene / isobutene copolymers, and their mixtures; - non-volatile polar hydrocarbon oils, in particular selected from: (i) fatty alcohols, saturated, unsaturated, linear or branched, of C10-C26, preferably mono-alcohols; in particular, C10-C26 alcohols are fatty alcohols, preferably branched when they comprise at least 16 carbon atoms; preferably, the fatty alcohol comprises from 10 to 24 carbon atoms, and more preferably from 12 to 22 carbon atoms, in particular lauryl, isostearyl, oleic alcohol, 2-butyloctanol, 2-undecyl pentadecanol, 2-hexyldecyl alcohol, isocetyl alcohol, octyldodecanol and mixtures thereof; (ii) triglycerides consisting of esters of fatty acids and glycerol, in particular those whose fatty acids may have chain lengths ranging from C4 to C36, and especially from C8 to C36, these oils which can be linear or branched, saturated or unsaturated; as well as mixtures thereof; iii) linear aliphatic hydrocarbon esters of formula RC(O)-OR' in which RC(O)-O- represents the carboxylic acid remainder comprising 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 in particular at least 10; (iv) hydroxylated esters, in particular polyglycerol-2 triisostearate; (v) aromatic esters, in particular tridecyl trimellitate, C12-C15 alcohol benzoate, 2-phenyl ethyl ester of benzoic acid, butyl octyl salicylate; vi) linear fatty acid esters having a total number of carbons ranging from 35 to 70, in particular pentaerythrityl tetrapelargonate; vii) C24-C28 branched fatty alcohol or fatty acid esters, in particular triisoarachidyl citrate, pentaerythrityl tetraisononanoate, glyceryl triisostearate, glyceryl tridecyl-2-tetradecanoate, pentaerythrityl tetraisostearate, polyglyceryl-2 tetraisostearate or pentaerythrityl tetradecanoate; (viii) polyesters obtained by condensation of dimer and / or trimer of unsaturated fatty acid and diol, in particular with INCI name dilinoleic acid / butanediol copolymer, dilinoleic acid / propanediol copolymer; polyesters obtained by condensation of fatty acid dimer and diol dimer, in particular dilinoleyl dimer dilinoleate; ix) synthetic ethers having 10 to 40 carbon atoms, in particular dicaprylyl ether; x) di-alkyl carbonates, the 2 alkyl chains being either identical or different, in particular dicaprylyl carbonate; xi) vinylpyrrolidone copolymers, in particular the vinylpyrrolidone / 1-hexadecene copolymer; and xii) mixtures thereof; - non-volatile carbonate oils, in particular selected from carbonates of the formula R8-OC(O)-O-R9, with R8 and R9 being identical or different, representing an alkyl chain in C4 to Ci2, and preferably from C6 to C10, linear or branched; - the oils called non-volatile ether oil of formula RrO-R2 in which Ri and R2 independently designate a linear, branched or cyclic C6-C24 alkyl group, preferably a C6-C18 alkyl group, and preferably a C8-C12 alkyl group; more preferably the volatile oil(s) are chosen from C8-C16 alkanes, in particular branched, preferably isododecane, isodecane and mixtures thereof, and the non-volatile oil(s) are chosen from isononyl isononanoate and 2-octyldodecanol and mixtures thereof.

7. A process for treating, in particular for cosmetic purposes, keratinous materials, especially for the care and / or makeup of the skin, lips, eyelashes and / or eyebrows and / or for the care, styling and / or coloring of keratinous fibers, preferably hair, comprising the application to said keratinous materials of i) at least one polyester of formula (I) comprising at least two acetoacetate functions, according to any one of claims 1 to 3, included in a composition, referred to as "Cl", comprising i), optionally iv) at least one cosmetic active ingredient, in particular according to claim 5; preferably, composition "Cl" does not include ii) a crosslinking agent; or - said polyester of formula (I) being included in a composition, referred to as "C2", comprising i), ii) at least one crosslinking agent, in particular according to claim 4, and optionally iv) at least one cosmetic active ingredient, in particular according to claim 5;preferably, composition "C2" does not include (iv) any cosmetic active ingredient; or - said polyester of formula (I) being included in a composition, referred to as "C3", comprising (i), (ii) at least one crosslinking agent, in particular according to claim 4, (iv) at least one cosmetic active ingredient, in particular according to claim 5, and preferably selected from coloring materials, preferably pigments, it being understood that compositions "C1", "C2" and / or "C3" may include (v) one or more fats, in particular at least one oil according to claim 6, preferably volatile, more preferably isododecane.

8. A treatment method according to claim 7, characterized in that it comprises either a single step of applying composition "C2" or composition "C3" to said keratin materials; or two successive steps of applying to said keratin materials two different compositions, preferably composition "Cl" followed by a composition referred to as "C4" comprising: ii) at least one crosslinking agent, in particular according to claim 4, and optionally iv) at least one cosmetic active ingredient, in particular according to claim 5; preferably, composition "C4" does not comprise i) at least one polyester of formula (I), its optical, geometric isomers, its organic or mineral acid or base salts, and / or solvates, such as hydrates, as defined in any one of claims 1 to 3;or three successive application steps on said keratinous materials, of three different compositions, preferably of composition "Cl" then of composition "C4" then of a composition called "C5" comprising: iv) at least one cosmetic active, in particular according to claim 5; preferably, composition "C5" does not comprise i) at least one polyester of formula (I) its optical, geometric isomers, its organic or mineral acid or base salts, and / or solvated, such as hydrates, as defined in any one of claims 1 to 3, and does not comprise ii) at least one crosslinking agent as defined in claim 4.;

9. A cosmetic treatment method for coloring keratin fibers, in particular hair, and / or for applying makeup to keratin materials, in particular skin, comprising applying to said keratin materials at least: - a composition, referred to as "C2", comprising i) at least one polyester of formula (I) comprising at least two acetoacetate functional groups according to any one of claims 1 to 3, ii) at least one crosslinking agent, in particular according to claim 4, and optionally iv) at least one cosmetic active ingredient, in particular according to claim 5; preferably, composition "C2" does not comprise iv) any cosmetic active ingredient; or - a composition, referred to as "C3", comprising i) at least one polyester of formula (I) comprising at least two acetoacetate functional groups according to any one of claims 1 to 3, ii) at least one crosslinking agent, in particular according to claim 4, and iv) at least one cosmetic active, in particular according to claim 5; it being understood that compositions “C2” or “C3” may comprise v) one or more fats, in particular according to claim 6.

10. A cosmetic treatment process for keratin fibers, for styling keratin fibers, preferably hair, comprising applying to said keratin fibers at least: - at least one polyester of formula (I) comprising at least two acetoacetate functions according to any one of claims 1 to 3, or a composition, referred to as "Cl", comprising i) at least one polyester of formula (I) comprising at least two acetoacetate functions, according to any one of claims 1 to 3, and optionally iv) at least one cosmetic active, in particular according to claim 5; preferably, composition "Cl" does not comprise ii) a crosslinking agent;or - a composition, referred to as "C2", comprising i) at least one polyester of formula (I) comprising at least two acetoacetate functions according to any one of claims 1 to 3, ii) at least one crosslinking agent, in particular according to claim 4, and optionally iv) at least one cosmetic active ingredient, in particular according to claim 5; preferably, composition "C2" does not comprise iv) a cosmetic active ingredient; or - a composition, referred to as "C3", comprising i) at least one polyester of formula (I) comprising at least two acetoacetate functions according to any one of claims 1 to 3, ii) at least one crosslinking agent, in particular according to claim 4, and iv) at least one cosmetic active ingredient, in particular according to claim 5; it being understood that compositions "C1" or "C2" or "C3" may comprise v) one or more fats, in particular according to claim 6.

11. Alkyd resin (B), characterized in that it is obtained from the reaction of an alkyd resin (A) containing ethylenic unsaturations with at least one (poly)hydroxy thiol, said alkyd resin (A) being obtained via: a) a first step by polycondensation of: - 0% to 12% mass of at least one compound comprising at least 3 alcohol functions; - 10% to 30% by mass of at least one diol; - 0% to 12% by mass of at least one dicarboxylic acid compound; - 20% to 50% by mass of at least one compound containing at least 3 carboxylic acid functions; - 35% to 60% by mass of at least one fatty alcohol; and - 0% to 20% by mass of at least one monocarboxylic acid compound, the mass percentages being expressed in relation to the total weight of the alkyd resin (A), it being understood that at least one of the dicarboxylic acid compounds and compounds containing at least 3 carboxylic acid functions, and / or at least one of the fatty alcohols, contains at least one ethylenic unsaturation;followed by b) a second step consisting of a thiol-ene reaction of all or part of the ethylenic unsaturations of the alkyd resin (A) obtained at the end of step a), with at least one (poly)hydroxy thiol, preferably of the following formula (Fl): RD-SH (Fl) in which RD represents a linear or branched C2-CiO hydrocarbon radical substituted by at least one hydroxy radical, preferably substituted by one or two hydroxy radicals.;

12. Polyester of the following formula (I) comprising at least two acetoacetate functions, as well as its optical, geometric, and / or solvated isomers, such as hydrates, or a composition containing it or them: (Z)-[OC(O)-C(Ra)(Rb)-C(O)-R4]u (I) formula (I) wherein: - u is an integer greater than 2; - R4 represents a monovalent hydrocarbon radical in the C1 to C6 group, linear or branched, saturated or unsaturated, preferably a (C1-C4)alkyl group, in particular methyl or tert-butyl, more preferably methyl; - Ra and Rb, identical or different, represent a hydrogen atom or a (C1-C4)alkyl group, preferably a hydrogen atom; and - Z denotes a multivalent radical derived from: I) of an alkyd resin (Al) obtained by polycondensation of: - 10% to 62% by mass, preferably 10% to 42% by mass of at least one polyol; - 10% to 62% by mass, preferably 10% to 42% by mass of at least one polyacid; and - 35% to 60% mass of at least one fatty alcohol, of which at least one contains at least one ethylenic unsaturation, relative to the total weight of the alkyd resin (Al); Or II) of an alkyd resin (A2) obtained by polycondensation of: - 10% to 62% mass of at least one polyol, said at least one polyol being or comprising at least dipentaerythritol; - 10% to 62% by mass of at least one polyacid; and - 35% to 60% by mass of at least one mono-fatty acid; relative to the total weight of the alkyd resin (A2): Or III) of an alkyd resin (A3) obtained by polycondensation of: - 10% to 62% mass of at least one polyol, said at least one polyol being xylitol or comprising at least xylitol; - 10% to 62% by mass of at least one polyacid; and - 35% to 60% by mass of at least one mono-fatty acid; relative to the total weight of the alkyd resin (A3); Or ; IV) of an alkyd resin (A4) obtained by polycondensation of: - 10% to 62% mass of a mixture of at least two polyols, said mixture not containing dipentaerythritol or xylitol; - 10% to 62% by mass of at least one polyacid; and - 35% to 60% by mass of at least one mono-fatty acid; relative to the total weight of the alkyd resin (A4); Or V) of an alkyd resin (A5) obtained by polycondensation of: - 10% to 62% mass of a single polyol other than pentaerythritol and xylitol; - 10% to 62% by mass of at least one polyacid; and - 35% to 60% by mass of a mixture of at least two mono-fatty acids; relative to the total weight of the alkyd resin (A5); Or VI) of an alkyd resin (A6) obtained by polycondensation of: - 10% to 62% mass of a polyol other than dipentaerythritol and xylitol; - 10% to 62% by mass of at least one polyacid; and - 35% to 60% by mass of a mono-fatty acid other than oleic acid; relative to the total weight of the alkyd resin (A6); or VII) of an alkyd resin (A7) obtained by polycondensation of: - 10% to 62% mass, preferably 10% to 42% mass of at least one polyol; - 10% to 62% by mass, preferably 10% to 42% by mass, of at least one polyacid, at least one of which contains at least one ethylenic unsaturation; and - 35% to 60% mass of at least one saturated fatty alcohol; relative to the total weight of the alkyd resin (A7).

13. A method for preparing polyester compounds of formula (I) comprising at least two acetoacetate functions according to claim 12, comprising at least one reaction step of all or part of the hydroxyl functions of at least one alkyd resin (Al), (A2), (A3), (A4), (A5), (A6) or (A7), preferably via a (trans)esterification reaction with a Gp-C(O)-C(Ra)(Rb)-C(O)-R4 ester, wherein Gp denotes a group starting preferably from a hydroxy radical or an (Ci-C4)alkoxy radical, such as methoxy, ethoxy, isobutoxy or t-butoxy, to form -OC(O)-C(Ra)(Rb)-C(O)-R4 esters with Ra, Rb and R4 being as defined in claim 12.

14. Composition, referred to as "C2", comprising i) at least one polyester of formula (I) comprising at least two acetoacetate functions as well as its optical, geometric and / or solvated isomers, such as hydrates, according to any one of claims 1 to 3, ii) at least one crosslinking agent, in particular according to claim 4, and optionally iv) at least one cosmetic active, in particular according to claim 5, preferably, composition "C2" does not comprise iv) any cosmetic active; and in particular further comprising v) one or more fats, preferably at least one oil, in particular according to claim 6.

15. Composition referred to as "C3", comprising i) at least one polyester of formula (I) comprising at least two acetoacetate functions as well as its optical, geometric and / or solvated isomers, such as hydrates, according to any one of claims 1 to 3, ii) at least one crosslinking agent, in particular according to claim 4, and iv) at least one cosmetic active, in particular according to claim 5; and in particular further comprising v) one or more fats, preferably at least one oil, in particular according to claim 6.

Citation Information

Patent Citations

  • cosmetic and dermatological light protection formulations containing bis-resorcinyltriazine derivatives and benzoxazole derivatives

    DE10162844A1

  • Oil-in-water or multiple emulsion with high concentration of suspended UVB filter

    DE19726184A1

  • Use of 4,4-di:aryl-butadiene derivatives as photostable UV filter compounds

    DE19746654A1

  • Use of 4,4-diarylbutadienes as photostable UV filters in cosmetics

    DE19755649A1

  • dimeric alpha-alkyl styrene derivatives as photostable UV filters in cosmetic and pharmaceutical preparations

    DE19855649A1