WO2024126625A1

WO2024126625A1 - Keratin material treatment process using at least one polysaccharide compound bearing acetoacetate functions

Info

Publication number: WO2024126625A1
Application number: PCT/EP2023/085699
Authority: WO
Inventors: Laurent SABATIE; Etienne SAVONNET; Boris STEVANT
Original assignee: LOreal SA
Current assignee: LOreal SA
Priority date: 2022-12-13
Filing date: 2023-12-13
Publication date: 2024-06-20
Anticipated expiration: 2025-06-13
Also published as: FR3142898A1

Abstract

Keratin material treatment process using at least one polysaccharide compound bearing acetoacetate functions The present invention relates to a process for treating keratin materials, comprising the application to said keratin materials, in one or more successive steps, of at least i) one or more compounds of formula (I) and also the optical and geometrical isomers thereof, the acid or base salts thereof, and/or the solvates thereof, such as the hydrates, or a composition containing same: (I) in which formula (I) X, R¹, R², R^a, R^b and n are as defined in the description, optionally ii) at least one crosslinking agent, optionally iii) water.

Description

Title: Keratin material treatment process using at least one polysaccharide compound bearing acetoacetate functions

Technical field

The present invention relates more particularly to the cosmetic field of keratin materials, and notably to that of caring for and/or making up the skin and/or lips and/or eyelashes and/or eyebrows, and that of caring for, styling and/or dyeing keratin fibres and preferably the hair. The aim is thus to propose novel treatment processes, notably cosmetic treatment processes, comprising the application to keratin materials of an oligosaccharide/polysaccharide compound bearing acetoacetate functions, and optionally a crosslinking agent, which are most particularly advantageous in terms of their technical performance, notably in terms of the resistance of the deposits they make it possible to obtain, and the sensorial experience they give the user.

Prior art

Cosmetic products conventionally require the use of one or more film-forming polymers in order to obtain a quality deposit of these products on keratin materials, and in particular to satisfy the expectations detailed below.

Thus, in the field of skin and/or lip makeup, it is most particularly expected that the deposit formed does not transfer on contact with the fingers or clothing.

It must also have good resistance to contact with water, notably rain or during showering or even perspiration, and also to sebum, or even to contact with food fats, notably food oils when this deposit is formed on the lips. Moreover, this deposit must be comfortable. Depending on the application or consumer demand, deposits are also sought for which the appearance can be varied from glossy to matt.

For this purpose, dispersions of polymer particles of nanometric size are used as filmforming agent in makeup products such as mascaras, eyeliners, eyeshadows or lipsticks, and in products for haircare application, and more particularly in their organic and notably oily phases.

However, the wear property over time of prior art compositions, in particular as regards the hairstyle, is not always satisfactory. Moreover, there is strong consumer demand for the use of more natural compositions, using compounds of natural origin that are possibly modified.

Moreover, in the field of haircare, a new range of products known as “Hair Makeup” has recently been developed. These products guarantee temporary hair dyeing that lasts after 1 to 3 shampoo washes.

They are thus a particularly attractive alternative for consumers to permanent hair dyeing, provided, of course, that the colouring effect is effectively guaranteed to last after contact with water and a few shampoo washes.

This requirement is also notably satisfied by the use of effective film-forming agents. Compositions are also known, notably film-forming cosmetic compositions, comprising at least one fatty phase and at least one copolymer obtained by polymerization of ethylenic monomers, some of which bear particular groups (see, for example, WO 2022/136104). Such compositions nevertheless require the presence of a fatty phase, which may reduce the field to certain applications. Furthermore, such compositions do not necessarily meet the need for naturalness expressed by certain consumers.

Thus, document FR 2741 530 proposes for this purpose, for the temporary dyeing of keratin fibres, the use of a dispersion of film-forming polymer particles including at least one acidic function and at least one pigment dispersed in the continuous phase of said dispersion. The colourings obtained via this dyeing method nevertheless have the drawback of being removed easily on shampoo washing.

It is moreover proposed in document FR 2 907 678 to perform coloured coating of the hair using a composition comprising a polysiloxane/polyurea block copolymer and a pigment. However, with such a composition, the coating results obtained are not always very homogeneous and the hair strand separation is not always very good.

It is also known practice from patent EP 1 392 222 to use a cosmetic composition for caring for and/or treating keratin materials, comprising a supramolecular polymer including a polymer backbone and at least two groups that are capable of forming at least three hydrogen bonds, and from patent EP 1 435 900 to use a hair composition comprising a supramolecular polymer including a polymer backbone and at least two groups that are capable of forming at least three hydrogen bonds and a surfactant or a hair-conditioning agent. However, with these two composition alternatives, the obtained performance with respect to styling hold over time or with respect to water remains insufficient. Processes for preparing compositions comprising modified polysaccharides are also known from WO 2020/026143. Moreover, US 2006/0079599 describes a polymer-based tissue adhesive for medical use, including polyvinyl alcohol polymers bearing ACAC groups combined with polyamines in the form of a hydrogel. US 3342806 and US 3361585 describe acetoacetylated starch compounds.

In general, the treatments and processes described above do not make it possible to obtain deposits, either on keratin fibres or on the skin and lips, which satisfy all the abovementioned requirements, namely very good water persistence, in particular to shampoo washing for the hair, and/or resistance to greasy substances notably for the lips, which are moreover comfortable to wear for the users, which make it possible to adjust the gloss, mattness or invisibility qualities and which, in the case of haircare use, provide very satisfactory styling hold or colour persistence, while at the same time meeting the need for naturalness expressed by certain consumers and/or formulations in which the presence of a fatty phase is not desired.

Disclosure of the invention

There is thus still a need for a treatment process, notably a cosmetic treatment process, intended for application to the skin, which makes it possible to obtain a deposit that is non- tacky, transfers little, if at all, is glossy or matt, comfortable, persistent and the use of which does not necessarily require the presence of a fatty phase, while at the same time being of natural origin.

There is also still a need for a treatment process, notably a cosmetic treatment process, which allows deposits to be obtained that are resistant to water and fatty substances, in particular sebum.

There is also still a need for a treatment process, notably a cosmetic treatment process, which affords deposits that have shiny and/or matt and/or invisibility qualities.

There is also a need for a treatment process, notably a cosmetic treatment process, which is colouring and intended for application to the hair and which affords deposits that have good persistence to water and shampoo washing in order to ensure a colour persistence over time that is comparable to direct dyeing. There is also a need for a treatment process, notably a cosmetic treatment process, which is non-colouring and intended for application to the hair and which affords water-persistent styling properties, notably curl hold.

The present invention is specifically directed towards meeting all or some of these needs.

Summary of the invention

These problems are solved by performing a process for treating keratin materials, comprising the application to said keratin materials, in one or more successive steps, of at least: i) one or more compounds of formula (I) and also the optical or geometrical isomers thereof, the acid or base salts thereof and/or solvates thereof, such as hydrates, or a composition containing same:

in which formula (I):

- R¹ represents a linear or cyclic, preferably linear, multivalent polysaccharide radical consisting of at least 3 monosaccharide units, each comprising at least 5 carbon atoms, particularly between 7 and 9 carbon atoms, preferably at least 6 carbon atoms, more particularly between 6 and 8 carbon atoms, and more preferentially 6 carbon atoms, and in which one or more of the hydroxyl (-OH), carbonyl (-C(O)), carboxyl (-C(O)-OH) or amino -NH2 groups, of all or part of at least one of the monosaccharide units, are optionally substituted with one or more groups R³;

- R² represents a linear or branched, saturated or unsaturated Ci-Ce monovalent hydrocarbonbased radical, preferably a (Ci-C4)alkyl group, more preferentially methyl;

- R³, which may be identical or different, represents a group chosen from:

1) sulfonate -SO3’, Cat⁺,

2) linear or branched (Ci-C22)alkyl, and

3) linear or branched (Ci-C22)alkylcarbonyl, the (Ci-C22)alkyl group being optionally interrupted with one or more heteroatoms or groups X as defined hereinbelow; and/or the (Ci-C22)alkyl group being optionally substituted with one or more groups chosen from: a) hydroxyl (-OH); b) sulfonate -SO3’, Cat⁺; c) sulfate -O-SO3’, Cat⁺; d) -(CH2-CH2-O)_P-R⁴; e) -O-(CH₂-CH₂-O)_P-R⁴; f) -C(O)-R⁴; g) -C(O)-O-R⁴; h) -O-C(O)-R⁴; i) -C(O)-N(R’)-R⁴; j) -N(R’)-C(O)-R⁴; k) ammonium -N⁺R”3; An’ and 1) mixtures thereof;

- R⁴ represents a hydrogen atom or a linear or branched (Ci-Cs)alkyl group, preferably R⁴ represents a hydrogen atom or a linear or branched (Ci-C6)alkyl group, more preferentially a linear or branched (Ci-C4)alkyl group, in particular methyl;

- R^a and R^b, which may be identical or different, represent a hydrogen atom or a (Ci-C4)alkyl group, preferably a hydrogen atom;

- X is a heteroatom or group chosen from -O-, -S-, -N(R’)-, and combinations thereof such as -C(O)-O-, -O-C(O)-, -C(O)-N(R’)-, -N(R’)-C(O)-, -N(R’)-C(O)-O-, -N(R’)-C(O)-N(R’)- , preferably X represents -O-;

- R’, which may be identical or different, represents a hydrogen atom or a linear or branched (Ci-C6)alkyl group optionally substituted with at least one hydroxyl group (OH), preferably R’ represents a hydrogen atom or a (Ci-C4)alkyl group, in particular methyl, more preferentially R’ represents a hydrogen atom;

- R”, which may be identical or different, represents a hydrogen atom or a linear or branched (Ci-C6)alkyl group, preferably a (Ci-C4)alkyl group, in particular methyl;

- n denotes an integer ranging from 2 to 3000, in particular from 5 to 2500, more particularly from 10 to 2300, preferably from 15 to 1000, preferentially from 20 to 500, and more preferentially from 25 to 200;

- p denotes an integer ranging from 0 to 3;

- An’ represents an anionic counterion;

- Cat’ represents a cationic counterion; ii) optionally at least one crosslinking agent; and iii) optionally water, preferably water, or optionally water mixed with a polar organic solvent, preferably chosen from (C2-C6)alkanols, more preferentially ethanol.

According to a particular embodiment, the present invention is directed to a process for treating keratin materials, comprising the application to said keratin materials, in one or more successive steps, of at least: i) one or more compounds of formula (I) and also the optical or geometrical isomers thereof, the acid or base salts thereof and/or solvates thereof, such as hydrates, or a composition containing same:

in which formula (I):

- R² represents a linear or branched, saturated or unsaturated Ci-Ce monovalent hydrocarbon-based radical, preferably a (Ci-C4)alkyl group, more preferentially methyl;

- R³, which may be identical or different, represents a group chosen from:

1) sulfonate -SO3’, Cat⁺,

2) linear or branched (Ci-C22)alkyl, and

3) linear or branched (Ci-C22)alkylcarbonyl, the (Ci-C22)alkyl group being optionally interrupted with one or more heteroatoms or groups X as defined hereinbelow; and/or the (Ci-C22)alkyl group being optionally substituted with one or more groups chosen from: a) hydroxyl (-OH); b) sulfonate -SO3’, Cat⁺; c) sulfate -O-SO3’, Cat⁺; d) -(CH2-CH2-O)_P- R⁴; e) -O-(CH₂-CH₂-O)_P-R⁴; f) -C(O)-R⁴; g) -C(O)-O-R⁴; h) -O-C(O)-R⁴; i) -C(O)-N(R’)- R⁴; j) -N(R’)-C(O)-R⁴; k) ammonium -N⁺R”3; An’ and 1) mixtures thereof;

- R⁴ represents a hydrogen atom or a linear or branched (Ci-Cs)alkyl group, preferably R⁴ represents a hydrogen atom or a linear or branched (C 1 -Cejalkyl group, more preferentially a linear or branched (Ci-C4)alkyl group, in particular methyl; - R^a and R^b, which may be identical or different, represent a hydrogen atom or a (Ci- C4)alkyl group, preferably a hydrogen atom;

- X is a heteroatom or group chosen from -O-, -S-, -N(R’)-, and combinations thereof such as -C(O)-O-, -O-C(O)-, -C(O)-N(R’)-, -N(R’)-C(O)-, -N(R’)-C(O)-O-, -N(R’)-C(O)- N(R’)-, preferably X represents -O-;

- R’ , which may be identical or different, represents a hydrogen atom or a linear or branched (Ci-C6)alkyl group optionally substituted with at least one hydroxyl group (OH), preferably R’ represents a hydrogen atom or a (Ci-C4)alkyl group, in particular methyl, more preferentially R’ represents a hydrogen atom;

- p denotes an integer ranging from 0 to 3;

- An’ represents an anionic counterion;

- Cat’ represents a cationic counterion; the compound(s) of formula (I) and also the optical and geometrical isomers thereof, the organic or mineral acid or base salts thereof, and the solvates thereof, being present in a content of at least 2% by weight, relative to the total weight of the composition containing them; ii) optionally at least one crosslinking agent; and iii) optionally water, preferably water, or optionally water mixed with a polar organic solvent, preferably chosen from (C2-C6)alkanols, more preferentially ethanol.

According to a preferred embodiment, the treatment process according to the invention comprises the application to said keratin materials of at least iii) water.

According to a preferred embodiment, the treatment process according to the invention comprises the application to said keratin materials of at least ii) a crosslinking agent.

According to a preferred embodiment, the treatment process according to the invention also comprises the application of at least iv) a cosmetic active agent, to said keratin materials.

According to a preferred embodiment, the process according to the invention comprises the application i) of at least one compound of formula (I), the optical or geometrical isomers thereof, the acid or base salts thereof, and/or the solvates thereof, such as hydrates, or of a composition containing same, optionally the application ii) of at least one crosslinking agent, iii) optionally of water and the application iv) of at least one cosmetic active agent, to said keratin materials.

According to one embodiment, the process comprises the application of i), optionally ii) and optionally iv) to damp or wet keratin materials.

The inventors thus found, surprisingly, that the application to keratin materials of the ingredients i), and optionally ii), iii) and iv), makes it possible to obtain deposits on the skin which have good resistance to external attacking factors, for instance water, oils, notably food oils, sweat and/or sebum, and which are therefore endowed with very good persistence over time. Advantageously, the deposits obtained via the processes according to the invention are also very comfortable. They are not tacky and do not transfer. Applying ingredients i), and possibly ii), iii) and iv) to keratin materials also affords deposits on keratin fibres which show good persistence to shampoo washing and to water.

Applying ingredients i), and possibly ii), iii) and iv) to keratin materials also affords deposits that are glossy or matt, depending on the nature of the ingredients i) used.

DEFINITIONS

For the purposes of the present invention and unless otherwise indicated:

- The term “multivalent” refers to a radical which is at least divalent; the valency of the radical Ri is equal to n as defined previously, the radical Ri thus being “n- valent”. By way of example, when n is equal to 3, the radical Ri is trivalent.

- For the purpose of the present invention, the term “keratin materials” is notably understood to denote the lips, skin, nails and keratin fibres, in particular the eyelashes, eyebrows and hair, preferably the lips and/or the hair.

- The term “cosmetic active agent” means an organic or organosilicon compound or a mineral compound which can be incorporated into a cosmetic composition to give an effect on keratin materials, whether this effect is immediate or provided by repeated applications. As examples of cosmetic active agents, mention may be made of coloured or uncoloured, fluorescent or non-fluorescent compounds such as optical brighteners, or UVA and/or UVB screening agents, anti-ageing active agents or active agents intended for providing a benefit to the skin such as active agents having action on the barrier function, deodorant active agents, antiperspirant active agents, desquamating active agents, antioxidant active agents, moisturizing active agents, sebum-regulating active agents, active agents intended for combating the effects of pollution, antimicrobial or bactericidal active agents, fragrances and dyestuffs such as direct dyes or pigments, preferably pigments.

Preferentially, the cosmetic active agents are chosen from a) dyestuffs chosen from pigments, direct dyes, and mixtures thereof, b) active agents for caring for keratin materials, preferably the skin, c) UV-screening agents, and d) mixtures thereof.

- For the purposes of the present invention, the term “fatty substance” means an organic compound that is insoluble in water at ordinary temperature (25°C) and at atmospheric pressure (760 mmHg) (solubility of less than 5%, preferably less than 1% and even more preferentially less than 0.1%); in addition, the fatty substances are soluble in organic solvents under the same temperature and pressure conditions, for instance in halogenated solvents such as chloroform or dichloromethane, lower alcohols such as ethanol or aromatic solvents such as benzene or toluene.

- The term “alkyl group” means a linear or branched, saturated hydrocarbon-based radical.

- The term “(C_x-C_y)alkyl group” means an alkyl group comprising from x to y carbon atoms.

- The term “(hetero)aryl” means aryl or heteroaryl groups.

- The term “(hetero)cycloalkyl” means cycloalkyl or heterocycloalkyl groups.

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

The cyclic or heterocyclic part of a non-aromatic radical may be substituted with at least one substituent borne by a carbon atom, chosen from the following groups: hydroxyl;

C1-C4 alkoxy, C2-C4 (poly )hydroxy alkoxy; alkylcarbonylamino ((R-C(O)-N(R’)-), in which the radical R’ is a hydrogen atom or a C1-C4 alkyl radical and the radical R is a C1-C2 alkyl radical or an amino radical substituted with one or two identical or different C1-C4 alkyl groups; alkylcarbonyloxy ((R-C(O)-O-), in which the radical R is a C1-C4 alkyl radical or an amino radical substituted with one or two identical or different C1-C4 alkyl groups; alkoxycarbonyl ((R-O-C(O)-) in which the radical R is a C1-C4 alkyl radical or an amino radical substituted with one or two identical or different C1-C4 alkyl groups;

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

- A hydrocarbon-based chain is unsaturated when it includes one or more double bonds and/or one or more triple bonds, which may or may not be conjugated.

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

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

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

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

- An “alkyl” radical is a linear or branched, in particular Ci-Ce and preferably C1-C4 saturated hydrocarbon-based radical.

- An “alkoxy” radical is an alkyl-oxy radical for which the alkyl radical is a linear or branched Ci-Ce and preferentially C1-C4 hydrocarbon-based radical.

- A “(poly)(hydroxy)alkyl” radical denotes a Ci-Ce and preferably C1-C4 alkyl radical optionally substituted with one or more hydroxyl radicals, preferably substituted with from 1 to 4 hydroxyl groups, more particularly between 1 and 3.

- A “sugar” radical is a monosaccharide or disaccharide radical. Sugar radicals that may be mentioned include: sucrose, glucose, galactose, ribose, fucose, maltose, fructose, mannose, arabinose, xylose, lactose.

- The term “monosaccharide” refers to a mono-oside sugar comprising at least 5 carbon atoms of formula C_x(H20)_x with x an integer greater than or equal to 5, preferably x is greater than or equal to 6, in particular x is between 5 and 7 inclusive, preferably x is equal to 6; they may be of D or L configuration, and of alpha or beta anomer, and also the salts thereof and the solvates thereof such as hydrates.

- The term “monosaccharide unit” means a mono-, di- or polyvalent monosaccharide radical.

- The term “polyvalent radical” means a radical which is at least divalent, such as a divalent, trivalent or tetravalent radical, preferably divalent or trivalent. - The term “disaccharide” refers to a di-oside sugar which is a compound constituted of two saccharides bonded together via O-oside bonds, said compounds being constituted of two monosaccharide units (also known as mono-osides) as defined previously, said monosaccharide units comprising at least 5 carbon atoms, preferably 6; in particular, the mono-oside units are linked together via a 1,4 or 1,6 bond as a (alpha) or p (beta) anomer, it being possible for each oside unit to be of L or D configuration, and also the salts thereof and the solvates thereof such as the hydrates of said monosaccharides; more particularly, they are polymers formed from two saccharides (or monosaccharides) having the general formula: -[C_x(H2O)_y)]2- or -[(CtkO h-, with x being an integer greater than or equal to 5, preferably x is greater than or equal to 6, in particular x is between 5 and 7 inclusive, preferably x is equal to 6, and y is an integer representing x - 1.

- The term “polysaccharide” refers to a poly-oside sugar which is a polymer constituted of at least two identical or different saccharides bonded together, preferably at least three saccharides bonded together via O-oside bonds, said polymers being constituted of monosaccharide units (also known as mono-osides) as defined previously, said monosaccharide units each comprising at least 5 carbon atoms, particularly between 7 and 9 carbon atoms, preferably at least 6 carbon atoms, more particularly between 6 and 8 carbon atoms, and more preferentially 6 carbon atoms; in particular, the mono-oside units are linked together via a 1,4 or 1,6 bond as a (alpha) or p (beta) anomer, it being possible for each oside unit to be of L or D configuration, and also the salts thereof and the solvates thereof such as the hydrates of said monosaccharides; more particularly, they are polymers formed from at least three saccharides (or monosaccharides) having the general formula: -[C_x(H20)_y)]_w- or -[(CH₂O)_X]_W-, where x is an integer greater than or equal to 5, preferably x is greater than or equal to 6, in particular x is between 5 and 7 inclusive and preferably x is equal to 6, and y is an integer which represents x - 1, and w is an integer greater than or equal to 2, particularly between 3 and 3000 inclusive, more particularly between 5 and 2500, preferentially between 10 and 2300, particularly between 15 and 1000 inclusive, more particularly between 20 and 500, preferentially between 25 and 200. These saccharides may optionally bear one or more anionic radicals such as the radicals -C(O)-OH, -SO3H, -O- SO3H or salts thereof -C(O)O“ Cat⁺, -SO3~Cat⁺, -O-SO3~Cat⁺ with Cat⁺ as defined previously.

- The expression “the groups hydroxyl (-OH), carbonyl (-C(O)), carboxy (-C(O)-OH) or amino NH2 are optionally substituted with one or more groups R³” means that the hydrogen atom of the group in question -OH, -C(O)-H, -C(O)-OH or -NH2 may be substituted with a group R³ to give -O-R³, -C(O)-R³, -C(O)-OR³ or -N(H)-R³; preferably when R³ represents an -SO3’, Cat⁺ group, then the substitution is performed on a hydroxyl group to give the -O- SO3’, Cat⁺ group.

- The term “linear polysaccharide radical” means a polysaccharide whose saccharide ends are not linked together; as examples of linear polysaccharide radicals, mention may be made of radicals derived from cellulose, starch, amylose, alginates, pectin, hyaluronic acid, dextrans, inulins, guar gums, glucans, carrageenans, pullulans and derivatives thereof; preferably pullulans and derivatives thereof such as myristoylpullulan.

- The term “cyclic polysaccharide radical” means a polysaccharide whose saccharide ends are linked together via O-oside bonds; cyclodextrin radicals may be mentioned as examples of cyclic polysaccharide radicals.

- The term “anionic counterion” means an anion or an anionic group associated with the cationic charge; more particularly, the anionic counterion is chosen from: i) halides such as chloride or bromide; ii) nitrates; iii) sulfonates, including Ci-Ce alkylsulfonates: Alk- S(O)₂O’ such as methylsulfonate or mesylate and ethylsulfonate; iv) arylsulfonates: Ar- S(O)₂O’ such as benzene sulfonate and toluenesulfonate or tosylate; v) citrate; vi) succinate; vii) tartrate; viii) lactate; ix) alkyl sulfates: Alk-O-S(O)O’ such as methyl sulfate and ethyl sulfate; x) aryl sulfates: Ar-O-S(O)O’ such as benzene sulfate and toluene sulfate; xi) alkoxy sulfates: Alk-O-S(O)2O“ such as methoxy sulfate and ethoxy sulfate; xii) aryloxy sulfates: Ar-O-S(O)2O“; xiii) phosphate; xiv) acetate; xv) triflate; and xvi) borates such as tetrafluoroborate, and mixtures thereof. The anionic counterion is chosen so that it ensures the electrical neutrality of the compounds of formula (I); when z cationic charges are to be neutralized, z anions of charge (-1) or z/2 anions of charge (-2) may thus be used.

- The term “cationic counterion” means a cation or a cationic group associated with the anionic charge; more particularly, the cationic counterion is preferably chosen from alkali metal or alkaline-earth metal salts such as sodium, potassium and calcium salts and mixtures thereof. The cationic counterion(s) may also be organic, such as tri(Ci-C4)(alkyl)ammonium or trihydroxy(Ci-C4)alkylammonium.

It is understood that when the compound(s) of formula (I) comprise SO3’ or -O-SO3’ and ammonium -N⁺R”3 groups, the counterions Cat⁺ and An’, respectively, are present or absent, to ensure the electrical neutrality of the molecule (I). Thus, for example, the cationic counterion is chosen such that it ensures the electrical neutrality of the compounds of formula (I); and when z’ anionic charges are to be neutralized, z’ cations of charge (+1) or z72 cations of charge (+2) may thus be used.

- The “solvates” represent hydrates and also the combination with linear or branched C2-C6 alcohols, also known as (C2-C6)alkanols, such as ethanol, isopropanol or n-propanol.

- The term “UV-A screening agent” means a chromophore derived from a compound which screens out (or absorbs) UV-A ultraviolet rays at a wavelength of between 320 and 400 nm. A distinction may be made between short UV-A screening agents (which absorb rays at a wavelength of between 320 and 340 nm) and long UV-A screening agents (which absorb rays at a wavelength of between 340 and 400 nm).

- The term “UV-B screening agent” means a chromophore derived from a compound which screens out (or absorbs) UV-B ultraviolet rays at a wavelength of between 280 and 320 nm.

- The term “chromophore” means a radical derived from a colourless or coloured compound that is capable of absorbing UV and/or visible radiation at a wavelength k_ahs of between 250 and 800 nm. Preferably, the chromophore is coloured, i.e. it absorbs wavelengths in the visible range, i.e. preferably between 400 and 800 nm. Preferably, the chromophores appear coloured to the eye, particularly between 400 and 700 nm (Ullmann’s Encyclopedia, 2005, Wiley-VcH, Verlag “Dyes, General Survey”, § 2.1 Basic Principle of Color).

- The term “anhydrous composition” means that said composition contains an amount of less than 5% by weight of water, preferentially less than 3% by weight of water, better still less than 1% by weight of water, relative to the total weight of the composition in question; even more preferentially, the composition under consideration is free of water.

- The terms “colouring agent” and “dyestuff” are equivalent.

Throughout the description, including the claims, the term “including a” should be understood as being synonymous with “including at least one” or synonymous with “including one or more”, unless otherwise mentioned.

- The term “(co)polymer” means a homopolymer or a copolymer.

- The term “homopolymer” means a polymer derived from the repetition of polymer or monomer units, said monomers of which are all identical, i.e. of the same chemical nature (for example -A-A-A-...-A-A-),

- The term “copolymer” means a polymer derived from the repetition of polymer or monomer units, of which at least two repeating monomers are different, i.e. of different chemical nature (for example -A-B-A-A-...-B-A-, it being understood that A is different from B); preferably, the (co)polymer(s) of the invention are copolymers.

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

It is understood that the treatment processes according to the invention, and also the compositions used, are non-therapeutic.

Detailed description

PROCESS FOR TREATING KERATIN MATERIALS

The first subject of the invention is a treatment process in one or more steps using, on keratin materials, notably keratin fibres or the skin: i) at least one compound of formula (I) and also the optical and geometrical isomers thereof, the salts thereof with organic or mineral acids or bases, and/or the solvates thereof, such as the hydrates, as defined previously and hereinbelow, or a composition containing same; ii) optionally at least one crosslinking agent, in particular as defined below; iii) optionally water; and iv) optionally at least one cosmetic active agent, in particular as defined previously and hereinbelow.

According to a particular embodiment of the invention, the treatment process according to the invention involves the simultaneous application of the ingredients i), optionally ii), optionally iii), and optionally iv).

According to another particular embodiment of the invention, the treatment process according to the invention comprises at least two steps in which the ingredients i), ii), optionally iii), and optionally iv), are applied in separate and successive steps to the keratin materials, it being understood that the cosmetic active agent(s) iv) may be present together with ingredient i) and/or with the ingredient(s) ii) and/or with ingredient iii) when it is present.

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

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

According to a particular embodiment of the invention, the process for treating keratin materials is a process, notably a cosmetic process, for treating keratin materials, in particular for caring for and/or making up the skin, the lips, the eyelashes and/or the eyebrows and/or for caring for, styling and/or colouring keratin fibres, preferably the hair.

According to a particular embodiment of the invention, the process for treating keratin materials is a cosmetic process for caring for, styling and/or colouring keratin fibres, preferably the hair.

According to another embodiment of the invention, the keratin material treatment process is a skincare process.

According to another embodiment of the invention, the keratin material treatment process is a makeup process for the skin, the lips, the eyelashes and the eyebrows. According to this embodiment, the process comprises at least one cosmetic active agent chosen from dyestuffs, preferably pigments.

According to one aspect of the invention, the process for treating keratin materials according to the invention using ingredients i), optionally ii), optionally iii), and optionally iv), is a treatment for colouring keratin fibres.

According to another aspect of the invention, the process for treating keratin materials according to the invention using the ingredients i), optionally ii), optionally iii) and optionally iv), is a skincare process.

According to one embodiment of the invention, the process according to the invention is a process for treating, notably for cosmetically treating, keratin materials, in particular for caring for and/or making up the skin, the lips, the eyelashes and/or the eyebrows and/or for caring for, styling and/or colouring keratin fibres, preferably the hair, comprising the application to said keratin materials of at least: - a composition, termed “Cl”, comprising i) at least one compound of formula (I) and also the optical and geometrical isomers thereof, the salts thereof with an organic or mineral acid or base, and/or the solvates thereof, such as hydrates, as defined previously and hereinbelow, optionally iii) water, and optionally iv) at least one cosmetic active agent, in particular as defined previously and hereinbelow;

- a composition, termed “C2”, comprising i) at least one compound of formula (I) and also the optical and geometrical isomers thereof, the salts thereof with an organic or mineral acid or base, and/or the solvates thereof, such as the hydrates, as defined previously and hereinbelow, optionally ii) at least one crosslinking agent, in particular as defined previously and hereinbelow, optionally iii) water, and optionally iv) at least one cosmetic active agent, in particular as defined previously and hereinbelow;

- a composition, termed “C3”, comprising i) at least one compound of formula (I) and also the optical and geometrical isomers thereof, the salts thereof with an organic or mineral acid or base, and/or the solvates thereof, such as the hydrates, as defined previously and hereinbelow, ii) at least one crosslinking agent, in particular as defined previously and hereinbelow, iv) at least one cosmetic active agent, in particular as defined previously and hereinbelow, and optionally iii) water;

- a composition, termed “C4”, comprising ii) at least one crosslinking agent, in particular as defined previously and hereinbelow, optionally iv) at least one cosmetic active agent, in particular as defined previously and hereinbelow, and optionally iii) water; and/or

- a composition, termed “C5”, comprising iv) at least one cosmetic active agent, in particular as defined previously and hereinbelow, and optionally iii) water; it being understood that compositions “Cl”, “C2”, “C3”, “C4” and “C5” may be anhydrous, aqueous, and/or comprise one or more fatty substances v), in particular as defined hereinbelow.

According to one embodiment of the invention, the process according to the invention is a process for treating, notably for cosmetically treating, keratin materials, in particular for caring for and/or making up the skin, the lips, the eyelashes and/or the eyebrows and/or for caring for, styling and/or colouring keratin fibres, preferably the hair, comprising the application to said keratin materials of at least:

- a composition, termed “Cl”, comprising i) at least one compound of formula (I) and also the optical and geometrical isomers thereof, the salts thereof with an organic or mineral acid or base, and/or the solvates thereof, such as hydrates, as defined previously and hereinbelow, optionally iii) water, and optionally iv) at least one cosmetic active agent, in particular as defined previously and hereinbelow, the compound(s) of formula (I) and also the optical and geometrical isomers thereof, the organic or mineral acid or base salts thereof, and the solvates thereof, being present in a content of at least 2% by weight, relative to the total weight of the composition;

- a composition, termed “C2”, comprising i) at least one compound of formula (I) and also the optical and geometrical isomers thereof, the salts thereof with an organic or mineral acid or base, and/or the solvates thereof, such as the hydrates, as defined previously and hereinbelow, optionally ii) at least one crosslinking agent, in particular as defined previously and hereinbelow, optionally iii) water, and optionally iv) at least one cosmetic active agent, in particular as defined previously and hereinbelow, the compound(s) of formula (I) and also the optical and geometrical isomers thereof, the organic or mineral acid or base salts thereof, and the solvates thereof, being present in a content of at least 2% by weight, relative to the total weight of the composition;

- a composition, termed “C3”, comprising i) at least one compound of formula (I) and also the optical and geometrical isomers thereof, the salts thereof with an organic or mineral acid or base, and/or the solvates thereof, such as the hydrates, as defined previously and hereinbelow, ii) at least one crosslinking agent, in particular as defined previously and hereinbelow, iv) at least one cosmetic active agent, in particular as defined previously and hereinbelow, and optionally iii) water, the compound(s) of formula (I) and also the optical and geometrical isomers thereof, the organic or mineral acid or base salts thereof, and the solvates thereof, being present in a content of at least 2% by weight, relative to the total weight of the composition;

- a composition, termed “C5”, comprising iv) at least one cosmetic active agent, in particular as defined previously and hereinbelow, and optionally iii) water; it being understood that compositions “Cl”, “C2”, “C3”, “C4” and “C5” may be anhydrous, aqueous, and/or comprise one or more fatty substances v), in particular as defined hereinbelow. According to one aspect of the invention, the process for treating keratin materials, in particular for caring for and/or making up the skin, the lips, the eyelashes and/or the eyebrows and/or for caring for, styling and/or colouring keratin fibres, preferably the hair, uses a composition, termed “Cl”, comprising i) at least one compound of formula (I) and also the optical and geometrical isomers thereof, the organic or mineral acid or base salts thereof, and/or the solvates thereof, such as hydrates, as defined previously and hereinbelow, optionally iii) water and optionally iv) at least one cosmetic active agent, in particular as defined hereinbelow, notably chosen from a) colouring agents, such as pigments, direct dyes, and mixtures thereof, b) active agents for caring for keratin materials, preferably the skin, c) UV-screening agents, and d) mixtures thereof, and notably at least one colouring agent, more particularly at least one pigment.

According to another aspect, the process for treating keratin materials according to the invention, in particular for caring for and/or making up the skin, the lips, the eyelashes and/or the eyebrows and/or for caring for, styling and/or colouring keratin fibres, preferably the hair, uses a composition, termed “C2”, comprising i) at least one compound of formula (I) and also the optical and geometrical isomers thereof, the organic or mineral acid or base salts thereof, and/or the solvates thereof, such as the hydrates, as defined previously and hereinbelow, optionally ii) at least one crosslinking agent, in particular as defined hereinbelow, optionally iii) water, and optionally iv) at least one cosmetic active agent, in particular as defined previously; preferably, said composition “C2” comprising iii) water.

According to another aspect, the process for treating keratin materials according to the invention, in particular for caring for and/or making up the skin, the lips, the eyelashes and/or the eyebrows and/or for caring for, styling and/or colouring keratin fibres, preferably the hair, uses a composition, termed “C3”, comprising i) at least one compound of formula (I) and also the optical and geometrical isomers thereof, the organic or mineral acid or base salts thereof, and/or the solvates thereof, such as the hydrates, as defined previously and hereinbelow, ii) at least one crosslinking agent, in particular as defined hereinbelow, iv) at least one cosmetic active agent, in particular as defined previously, and optionally iii) water. According to another aspect, the process for treating keratin materials according to the invention, in particular for caring for and/or making up the skin, the lips, the eyelashes and/or the eyebrows and/or for caring for, styling and/or colouring keratin fibres, uses a composition termed “Cl” and a composition termed “C4”, said composition “Cl” comprising i) at least one compound of formula (I) and also the optical and geometrical isomers thereof, and the organic or mineral acid or base salts thereof, and/or the solvates thereof, such as hydrates, as defined previously and hereinbelow, optionally iii) water, and optionally iv) at least one cosmetic active agent, in particular as defined previously and hereinbelow, and said composition “C4” comprising ii) at least one crosslinking agent, in particular as defined previously and hereinbelow, optionally iii) water, and optionally iv) at least one cosmetic active agent, in particular as defined previously and hereinbelow.

According to another variant of the process of the invention, the ingredient(s) i), optionally iii), and optionally iv) are applied together, i.e. simultaneously, to the keratin materials during a first step, then during a subsequent step, the ingredient(s) ii), optionally iii), and optionally iv) are applied to said materials.

According to a particular embodiment, the process according to the invention comprises two successive steps in which two different compositions are applied to said keratin materials.

According to a particular embodiment of the process, during the first step a composition “Cl” is applied to the keratin materials, then a composition “C4” is applied to said keratin materials.

According to yet another variant of the process of the invention, ingredient(s) ii) and optionally iv) are applied to the keratin materials, then ingredient(s) i), and optionally iv) at least one cosmetic active agent, in particular as defined previously, are applied to said keratin materials. In particular, composition “C4” is applied to the keratin materials and then composition “Cl” is applied.

According to another variant of the process according to the invention, a composition “Cl” containing i), and iii) optionally water, is applied, and sequentially a composition “C4” containing ii), optionally iii), and optionally iv), composition “Cl” preferably being applied before composition “C4”.

According to a particular embodiment of the process, during the first step a composition “C2” is applied to the keratin materials, then a composition “C4” is applied to said keratin materials.

According to another variant of the process according to the invention, a composition “C2” containing i) at least one compound of formula (I) and also the optical and geometrical isomers thereof, the organic or mineral acid or base salts thereof, and/or the solvates thereof, such as hydrates, optionally ii) at least one crosslinking agent, optionally iii) water, and optionally iv) at least one cosmetic active agent, is applied, and sequentially a composition “C4” containing ii) at least one crosslinking agent, optionally iii) water, and optionally iv) at least one cosmetic active agent, is applied, composition “C2” preferably being applied before composition “C4”, and it being understood that the optional crosslinking agent(s) contained in composition “C2” may be identical to or different from the crosslinking agent(s) contained in composition “C4”; preferably, the crosslinking agent(s) are different.

Compositions “Cl”, “C2”, “C3”, “C4” and/or “C5” of the process according to the invention, which comprise at least one fatty substance, notably at least one oil, and water, may be in the form of a direct or inverse emulsion.

Compositions “Cl”, “C2”, “C3”, “C4” and/or “C5” of the process according to the invention may thus be applied directly as such to the target keratin materials or may even be formed directly on the surface of these keratin materials.

According to the invention, three application methods known as the “one-gesture application mode”, the “two-gesture application mode” and the “three-gesture application mode” are thus distinguished.

According to one embodiment of the process of the invention, the process is performed in one gesture by applying composition “Cl”, “C2” or “C3”, as defined previously, to the keratin materials.

Thus, according to one embodiment, the treatment process according to the invention comprises a single step of applying composition “Cl” or composition “C2” or composition “C3” to said keratin materials.

The term “one-gesture application mode” means the direct application to the target keratin materials of a single composition complying with the invention, namely composition “Cl”, “C2” or “C3”.

After application of composition “Cl”, “C2” or “C3”, a persistent, non-tacky deposit is advantageously obtained. The deposit obtained is also resistant to food oils, water, sebum and friction.

According to another embodiment of the process of the invention, the process is performed in two gestures.

The term “two-gesture application mode” means the successive application, to the target keratin material, of two different compositions, for example “Cl” and “C4”, or “C2” and “C4”, or “C3” and “C4” Preferably “Cl” and then “C4”, “C2” and then “C4”, or “C3” and then “C4”.

According to another embodiment, the process of the invention is performed in three gestures.

The term “three-gesture application mode” means the sequential application of three different compositions “Cl” to “C5”. According to this application mode, for example, according to one embodiment, successive application is performed on the keratin materials, a) of a composition “Cl”, then P) of a composition “C4”, then y) of a composition “C5”, preferably “Cl” then “C4” or, respectively, “C5” or “C5” or, respectively, “C4”.

According to another embodiment, sequential application is performed on the keratin materials, a) of a composition, for example “C4”, and P) of a composition “Cl” or “C2”, and even y) of a composition “C5”; preferably, composition “C4” is applied before composition “Cl” or “C2”.

In the two- or three-gesture application modes, the composition applied first, for example “Cl”, is conventionally referred to as the “base coat”, and the composition(s) superposed thereon are generally referred to as the “top coat”.

After application of the various compositions “Cl” to “C5”, a persistent, non-tacky deposit is advantageously obtained. The deposit obtained is also persistent to food oils, water and shampoo washing.

According to a particular embodiment, the compositions are applied to dry keratin materials. According to a particular embodiment, the compositions are applied to damp or wet keratin materials, i.e. keratin materials containing water on the surface.

According to a particular embodiment, the keratin materials are dried after application of compositions “Cl” to “C5”, in particular after application of each different composition. The drying step can be implemented with a drying device such as a helmet, a hair dryer or a climazon. When the drying step is implemented with a helmet or a hair dryer, the drying temperature is comprised between 40 °C and 110 °C, preferably between 50 °C and 90°C. After the drying step, a step of shaping the keratin fibers can be implemented with a hair straightener, a straightening or curling iron or a steam iron, preferably a hair straightener or a steam iron. Preferably, the step of shaping the keratin fibres is carried out at a temperature ranging from 120 °C to 230 °C, notably from 150 °C to 210 °C, even more preferentially from 160 °C to 210 °C, better from 180 °C to 210 °C. The iron can be applied to the keratin fibers in successive separate touches of a few seconds, or by progressive movement or sliding along the hair. Preferably, the application of the iron is done in continuous movement from the root to the tip of the hair, in one or more passes.

According to one aspect, the present invention relates to a process for treating, notably for cosmetically treating, keratin materials, in particular for caring for and/or making up the skin, the lips, the eyelashes and/or the eyebrows and/or for caring for, styling and/or colouring keratin fibres, preferably the hair, comprising a step of applying to the skin or said lips or the eyelashes or the eyebrows a composition “Cl”, “C2” or “C3”, notably containing at least one dyestuff, in particular as defined previously, and more particularly at least one pigment.

According to another of its aspects, the present invention relates to a cosmetic treatment process for caring for, styling and/or colouring keratin fibres, preferably the hair, comprising the successive application of at least:

- a composition, termed “Cl”, comprising i) at least one compound of formula (I) and also the optical and geometrical isomers thereof, the organic or mineral acid or base salts thereof, and/or the solvates thereof, such as the hydrates, as defined previously and hereinbelow, optionally iii) water, and optionally iv) at least one cosmetic active agent, in particular as defined previously and hereinbelow; and then

- a composition, termed “C4”, comprising ii) at least one crosslinking agent, in particular as defined previously and hereinbelow, optionally iii) water, and optionally iv) at least one cosmetic active agent, in particular as defined previously and hereinbelow; at least one of the compositions “Cl” and/or “C4” containing at least one dyestuff, in particular as defined previously and hereinbelow, preferably at least one pigment, and more preferentially composition “Cl” comprises at least one pigment.

- a composition “Cl” as defined previously; and then

- a composition “C4” as defined previously; and then

- a composition “C5” as defined previously; it being understood that compositions “Cl” and/or “C4” and/or “C5” contain at least one dyestuff in particular as defined hereinbelow, preferably at least one pigment. Preferably, composition “C5” comprises at least one pigment.

- a composition “C2” or “C3” as defined previously; and

- a composition “C4” as defined previously; it being understood that compositions “C2” or “C3” contain at least iv) one dyestuff, in particular as defined hereinbelow, and/or composition “C4” contains at least one dyestuff, in particular as defined hereinbelow; preferably composition “C2” or “C3” comprises at least one pigment.

COMPOUNDS OF FORMULA (I)

As indicated above, the treatment process according to the invention comprises the application to keratin materials of at least one or more compounds chosen from oligosaccharides or polysaccharides bearing acetoacetate functions of formula (I) and also the optical and geometrical isomers thereof, the organic or mineral acid or base salts thereof, and/or the solvates thereof, such as hydrates, or a composition containing same.

Thus, the treatment process according to the invention comprises the application to the keratin materials of at least one or more compounds of formula (I) and also the optical and geometrical isomers thereof, the organic or mineral acid or base salts thereof, and/or the solvates thereof, such as the hydrates, or a composition containing same:

in which formula (I):

- R³, which may be identical or different, represents a group chosen from:

1) sulfonate -SO3’, Cat⁺,

2) linear or branched (Ci-C22)alkyl, and

- R⁴ represents a hydrogen atom or a linear or branched (Ci-Cs)alkyl group, preferably R⁴ represents a hydrogen atom or a linear or branched (C 1 -CoJal ky 1 group, more preferentially a linear or branched (Ci-C4)alkyl group, in particular methyl;

- R’, which may be identical or different, represents a hydrogen atom or a linear or branched (Ci-Ce/alkyl group optionally substituted with at least one hydroxyl group (OH), preferably R’ represents a hydrogen atom or a (Ci-C4)alkyl group, in particular methyl, more preferentially R’ represents a hydrogen atom;

- n denotes an integer ranging from 2 to 3000, in particular from 5 to 2500, more particularly from 10 to 2300, preferably from 15 to 1000, preferentially from 20 to 500, and more preferentially from 25 to 200; - p denotes an integer ranging from 0 to 3;

- An’ represents an anionic counterion;

According to a particular embodiment of the invention, R¹ represents a linear or cyclic, preferably linear, multivalent polysaccharide radical consisting of at least 3 monosaccharide units, each comprising at least 5 carbon atoms, preferably at least 6 carbon atoms, particularly between 6 and 8 carbon atoms, and more preferentially 6 carbon atoms, and in which none of the hydroxyl (-OH), carbonyl (-C(O)), carboxyl (-C(O)-OH) or amino -NH2 groups of the monosaccharide units are substituted.

According to another particular embodiment of the invention, the compounds of formula (I) are such that R¹ represents a linear or cyclic, preferably linear, multivalent polysaccharide radical consisting of at least 3 monosaccharide units each comprising at least 5 carbon atoms, preferably at least 6 carbon atoms, particularly comprising from 6 to 8 carbon atoms, and more preferentially 6 carbon atoms, and in which one or more of the hydroxyl (-OH) or amino -NH2 groups of all or part of at least one of the monosaccharide units are substituted with one or more identical or different groups R³ representing a (Ci-C22)alkylcarbonyl group, the (Ci-C22)alkyl group being:

- optionally interrupted with one or more oxygen or sulfur atoms or -N(H)-, preferably -O-, and/or optionally substituted with one or more groups chosen from: a) hydroxyl (-OH); b) sulfonate -SO₃’, Cat⁺; c) sulfate -O-SO₃’, Cat⁺; d) -(CH₂-CH₂-O)_P-R⁴; e) -O-(CH₂-CH₂-O)_P-R⁴; f) - C(O)-R⁴; g) -C(O)-O-R⁴; h) -O-C(O)-R⁴; i) -C(O)-N(R’)-R⁴; j) -N(R’)-C(O)-R⁴; k) ammonium -N⁺R”₃; An’ and 1) mixtures thereof; with R⁴ representing a hydrogen atom or a (Ci-Ce/alkyl group, more preferentially a (Ci-C4)alkyl group, such as methyl, R”, An- and Cat⁺ being as defined previously. Preferably, R” represents a (Ci-C4)alkyl group, such as methyl.

According to a particular embodiment of the invention, the compounds of formula (I) are such that R³, which may be identical or different, represents a (Ci-C22)alkylcarbonyl group, the (Ci-C22)alkyl group being optionally substituted with one or more groups chosen from a) hydroxyl (-OH); h) ammonium -N⁺R’ ’3, An’ and i) mixtures thereof; with R’ ’ representing a (Ci-C4)alkyl group, such as methyl.

More preferentially, the (Ci-C22)alkyl group of R³ represents a -CH2-CH(OH)-CH2- N⁺(CH3)3, An’ group.

According to a particular variant of the invention, the compounds of formula (I) are such that R¹ represents a linear or cyclic, preferably linear, multivalent polysaccharide radical consisting of at least 3 monosaccharide units each comprising at least 5 carbon atoms, preferably at least 6 carbon atoms, and more preferentially 6 carbon atoms, and in which one or more of the hydroxyl groups, of all or part of at least one of the monosaccharide units, are substituted with one or more groups R³, which may be identical or different, representing a sulfonate group -SO3’, Cat⁺.

According to another variant of the invention, R¹ represents a linear or cyclic, preferably linear, multivalent polysaccharide radical consisting of at least 3 monosaccharide units each comprising at least 5 carbon atoms, preferably at least 6 carbon atoms, particularly between 6 and 8 carbon atoms, and more preferentially 6 carbon atoms, and in which one or more of the hydroxyl (-OH), carbonyl (-C(O)), carboxyl (-C(O)-OH) or amino -NH2 groups, of all or part of at least one of the monosaccharide units, are substituted with one or more groups R³ with R³, which may be identical or different, representing a group chosen from:

1) sulfonate -SO3’, Cat⁺,

2) linear or branched (Ci-C22)alkyl, and

3) linear or branched (Ci-C22)alkylcarbonyl.

More preferentially, R¹ comprises one or more from among hydroxyl (-OH) or amino -NH2 groups, of all or part of at least one of the monosaccharide units, substituted with one or more groups R³ as defined previously. In particular, the -OH group is substituted with a group 1), 2) or 3), more particularly with a group 1) or 3), preferably with a group 3). In particular, the -NH2 group is substituted with a group 2) or 3), more particularly with a group 3).

According to a particular embodiment, the compound(s) of formula (I) and also the optical and geometrical isomers thereof, the organic or mineral acid or base salts thereof, and/or the solvates thereof according to the invention are such that the polysaccharide radical represented by R¹ is chosen from polysaccharide radicals derived from agarose, starch and derivatives thereof, cationic starch, alginate and derivatives thereof, hyaluronic acid, cellulose and derivatives thereof, in particular chosen from methylcellulose ethylcellulose, hydroxymethylcellulose, hydroxypropylcellulose, hydroxypropylmethylcellulose and hydroxybutylcellulose, carrageenan, curdlan, dextran, glucan, guar gum, gellan, konjac, inulin, pectin, pullulan, scleroglucan, xanthan, and raffinose, and derivatives thereof, preferably chosen from starch and derivatives thereof, cellulose and derivatives thereof, alginate and derivatives thereof, and raffinose and derivatives thereof, and more preferentially chosen from hydroxypropylcellulose, pullulan and derivatives thereof, such as myristoyl pullulan, and raffinose.

According to a particular embodiment, the compound(s) of formula (I) and also the optical and geometrical isomers thereof, the organic or mineral acid or base salts thereof, and/or the solvates thereof according to the invention are such that the polysaccharide radical represented by R¹ is chosen from polysaccharide radicals derived from agarose, starch and derivatives thereof, cationic starch, alginate and derivatives thereof, hyaluronic acid, cellulose and derivatives thereof, in particular chosen from methylcellulose ethylcellulose, hydroxymethylcellulose, hydroxypropylmethylcellulose and hydroxybutylcellulose, carrageenan, curdlan, dextran, glucan, guar gum, gellan, konjac, inulin, pectin, pullulan and scleroglucan, xanthan and derivatives thereof, preferably chosen from starch and derivatives thereof, cellulose and derivatives thereof and alginate and derivatives thereof, and more preferentially chosen from pullulan and derivatives thereof, such as myristoyl pullulan.

The term “derivative” means compounds obtained by chemical modification of the compounds mentioned. In particular, they may be esters, amides or ethers of said compounds.

The polysaccharide/oligosaccharide derivatives may be chosen, for example, from those described in the articles “Natural and modified polysaccharides”, Drug Targeting and Delivery (1997), 7, 275-289 and “Gums”, Kirk-Othmer Encyclopedia of Chemical Technology (2005), 13, 60-73.

The polysaccharide radicals R¹ may also be chosen from radicals derived from fatty-chain polysaccharide derivatives, in particular those described in “Enzymatic synthesis of oligo- and polysaccharide fatty acid esters”, Carbohydrate Polymers, (2013), 93(1), 65-72, “Chemical Modification of Polysaccharides”, Hindawi, Organic Chemistry, Volume 2013, Article ID 417672, or else in patent application CA2087488. According to a particular embodiment, the fatty-chain polysaccharides at the origin of the radicals Ri are chosen from myristoyl pullulan, stearoyl inulin, undecylenoyl inulin and palmitoyl hydroxypropylcellulose, preferably from fatty-chain esters, more preferentially myristoyl pullulan.

The polysaccharide/oligosaccharide derivatives may also be chosen from thiolated polysaccharides/oligosaccharides, in particular those described in the publication “Unsaturated and thiolated derivatives of polysaccharides as functional matrixes for tissue engineering and pharmacology: A review”, Carbohydrate Polymers, 2021, Volume 259, 117735.

According to a particular embodiment, the compounds of formula (I) bearing acetoacetate functions are chosen from: a) cellulose, starch, amylose and derivatives thereof, of formula (II) and also the optical isomers thereof, the organic or mineral acid or base salts thereof, and the solvates thereof, such as hydrates:

(II) b) alginate, pectin and derivatives thereof of formula (III) and also the optical isomers thereof, the organic or mineral acid or base salts thereof, and the solvates thereof, such as hydrates:

c) hyaluronic acid and derivatives thereof, of formula (IV) and also the isomers and solvates thereof:

(IV) d) dextran and derivatives thereof of formula (V) and also the optical isomers thereof, the organic or mineral acid or base salts thereof, and the solvates thereof, such as hydrates:

(V) e) inulin and derivatives thereof of formula (VI) and also the optical isomers thereof, the organic or mineral acid or base salts thereof, and the solvates thereof, such as hydrates:

(VI) f) guar gum and derivatives thereof of formula (VII) and also the optical isomers thereof, the organic or mineral acid or base salts thereof, and the solvates thereof, such as hydrates:

(VII) g) glucan and derivatives thereof of formula (VIII) and also the optical isomers thereof, the organic or mineral acid or base salts thereof, and the solvates thereof, such as hydrates:

(VIII) h) carrageenan and derivatives thereof, notably of formula (IX), and also the optical isomers thereof, the organic or mineral acid or base salts thereof, and the solvates thereof, such as hydrates:

(IX) in particular chosen from the derivatives y-carrageenan, 6- carrageenan, p-carrageenan, v- carrageenan, - carrageenan, and the respective basic forms thereof P-carrageenan, a- carrageenan, K- carrageenan, r-carrageenan, 9-carrageenan, it being understood that the carrageenans comprise at least one group of formula (XII), preferably at least two groups of formula (XII); i) cyclodextrin and derivatives thereof, of formula (X):

(X) j) pullulan and derivatives thereof of formula (XI) and also the optical isomers thereof, the organic or mineral acid or base salts thereof, and the solvates thereof, such as hydrates:

in which formulae (II) to (XI):

R⁶, which may be identical or different, represents -CH2-OR⁷ or -C(O)-OR⁷,

R⁷, which may be identical or different, represent a hydrogen atom or a group R³ as defined in formula (I), preferably a (Ci-C22)alkyl group, optionally substituted with at least one hydroxyl group (-OH) or a group -C(O)-R⁸, with R⁸ representing a (Ci-

C22)alkyl group, or a group -CH2-CH(OH)-CH2-N⁺(CH3)3 An’, or a group R⁹ of formula (XII), R⁷ represents a radical R⁷ or a group -SO3’, Cat ⁺, Cat⁺ being as defined previously, or a group of formula (XII):

(XII) in which formula (XII) R^a, R^b and R² are as defined previously for the compounds of formula

(I), preferably R² denotes a methyl radical and R^a and R^b denote a hydrogen atom;

R¹⁰, which may be identical or different, represent a hydrogen atom, a (Ci-C4)alkyl group, such as -CH3, or a group R⁹ as defined above; m denotes an integer ranging from 2 to 3000, in particular from 5 to 2500, more particularly from 10 to 2300, preferably from 15 to 1000, preferentially from 20 to 500, and more preferentially from 25 to 200;

An’ being as defined previously; it being understood that formulae (II) to (XI) contain at least one unit R⁹, and preferably at least two units R⁹, of formula (XII), in their structure.

According to a particular embodiment, the compounds of formula (I) bearing acetoacetate functions are chosen from compounds of formula (II) such as hydroxypropylcellulose bearing acetoacetate functions, compounds of formula (III), compounds of formula (IV), compounds of formula (V), compounds of formula (VI), compounds of formula (VII), compounds of formula (VIII), compounds of formula (IX), compounds of formula (X), and compounds of formula (XI) above and: k) raffinose and derivatives thereof of formula (XVI):

in which formulae (II) to (XI) and (XVI):

R⁶, which may be identical or different, represents -CH2-OR⁷ or -C(O)-OR⁷, R⁷, which may be identical or different, represent a hydrogen atom or a group R³ as defined in formula (I), preferably a (Ci-C22)alkyl group, optionally substituted with at least one hydroxyl group (-OH) or a group -C(O)-R⁸, with R⁸ representing a (Ci- C22)alkyl group, or a group -CH2-CH(OH)-CH2-N⁺(CH3)3 An’, or a group R⁹ of formula (XII), R⁷ represents a radical R⁷ or a group -SO3’, Cat ⁺, Cat⁺ being as defined previously, or a group of formula (XII):

(XII) in which formula (XII) R^a, R^b and R² are as defined previously for the compounds of formula (I), preferably R² denotes a methyl radical and R^a and R^b denote a hydrogen atom;

An’ being as defined previously; it being understood that formulae (II) to (XI) and (XVI) contain at least one unit R⁹, and preferably at least two units R⁹, of formula (XII), in their structure.

According to a particular embodiment, the polysaccharides and/or oligosaccharides bearing acetoacetate functions are chosen from:

- alginic acid 3-oxobutanoate (CAS No.: 2135428-65-6];

- amylose 3-oxobutanoate (CAS No.: 106254-13-1];

- cellulose, 3-oxobutanoate, 2-hydroxyethyl ether (CAS No.: 104708-71-6];

- cellulose, 3-oxobutanoate, carboxymethyl ether (CAS No.: 105953-68-2];

- cellulose, 3-oxobutanoate, 2-hydroxypropyl ether (CAS No.: 105953-69-3];

- cellulose, 3-oxobutanoate, methyl ether (CAS No.: 105953-70-6];

- cellulose, tris(3-oxobutanoate) (CAS No.: 119466-02-3];

- cellulose, 3-oxobutanoate (CAS No.: 80619-14-3];

- cellulose, acetate 3-oxobutanoate (CAS No.: 168608-38-6]; - cellulose, hexanoate 3-oxobutanoate (CAS No.: 1696417-96-5];

- cellulose, 3-oxobutanoate propanoate (CAS No.: 163381-45-1];

- cellulose, butanoate 3-oxobutanoate (CAS No.: 163438-87-7];

- cellulose, 4-methoxy-3-oxobutanoate (CAS No.: 2410687-10-2];

- cellulose, 3-oxobutanoate, 2-hydroxypropyl methyl ether (CAS No.: 2223678-14-4];

- cellulose, acetate butanoate 3-ethoxypropanoate 3-oxobutanoate (CAS No.: 334475-56-8];

- cellulose, 2-hydroxypropyl ether, 3-oxobutanoate (CAS No.: 497932-47-5];

- cellulose, 3-oxobutanoate, ethyl ether (CAS No.: 497932-48-6];

- dextran, 3-oxobutanoate (CAS No.: 882428-66-2];

- D-glucan, 3-oxobutanoate (CAS No.: 2135428-66-7];

- guar gum, 3-oxobutanoate (CAS No.: 497932-49-7];

- hyaluronic acid, 3-oxobutanoate (CAS No.: 2135428-62-3];

- starch, 3-oxobutanoate (CAS No.: 78207-15-5];

- starch, 3-oxobutanoate, methyl ether (CAS No.: 2135428-59-8];

- starch, 3-oxobutanoate, 2-carboxymethyl ether (CAS No.: 2135428-60-1];

- starch, 2-hydroxypropyl ether, 3-oxobutanoate (CAS No.: 2135428-61-2];

- starch, 3-oxobutanoate, 2-hydroxypropyl ether (CAS No.: 2223678-15-5];

- pullulan acetoacetate (CAS No.: 2762209-81-2];

- cyclodextrin, ethyl-3-oxobutanoate (CAS No.: 152154-93-3];

- cyclodextrin, 3-oxobutanoate (CAS No.: 2135428-63-4);

- myristoyl pullulan acetoacetate;

- raffinose acetoacetate; and

- hydroxypropylcellulose acetoacetate.

- alginic acid 3-oxobutanoate (CAS No.: 2135428-65-6];

- amylose 3-oxobutanoate (CAS No.: 106254-13-1];

- cellulose, 3-oxobutanoate, 2-hydroxyethyl ether (CAS No.: 104708-71-6];

- cellulose, 3-oxobutanoate, carboxymethyl ether (CAS No.: 105953-68-2];

- cellulose, 3-oxobutanoate, 2-hydroxypropyl ether (CAS No.: 105953-69-3];

- cellulose, 3-oxobutanoate, methyl ether (CAS No.: 105953-70-6];

- cellulose, tris(3-oxobutanoate) (CAS No.: 119466-02-3]; - cellulose, 3-oxobutanoate (CAS No.: 80619-14-3];

- cellulose, acetate 3-oxobutanoate (CAS No.: 168608-38-6];

- cellulose, hexanoate 3-oxobutanoate (CAS No.: 1696417-96-5];

- cellulose, 3-oxobutanoate propanoate (CAS No.: 163381-45-1];

- cellulose, butanoate 3-oxobutanoate (CAS No.: 163438-87-7];

- cellulose, 4-methoxy-3-oxobutanoate (CAS No.: 2410687-10-2];

- cellulose, 2-hydroxypropyl ether, 3-oxobutanoate (CAS No.: 497932-47-5];

- cellulose, 3-oxobutanoate, ethyl ether (CAS No.: 497932-48-6];

- dextran, 3-oxobutanoate (CAS No.: 882428-66-2];

- D-glucan, 3-oxobutanoate (CAS No.: 2135428-66-7];

- guar gum, 3-oxobutanoate (CAS No.: 497932-49-7];

- hyaluronic acid, 3-oxobutanoate (CAS No.: 2135428-62-3];

- starch, 3-oxobutanoate (CAS No.: 78207-15-5];

- starch, 3-oxobutanoate, methyl ether (CAS No.: 2135428-59-8];

- starch, 3-oxobutanoate, 2-carboxymethyl ether (CAS No.: 2135428-60-1];

- starch, 2-hydroxypropyl ether, 3-oxobutanoate (CAS No.: 2135428-61-2];

- starch, 3-oxobutanoate, 2-hydroxypropyl ether (CAS No.: 2223678-15-5];

- pullulan acetoacetate (CAS No.: 2762209-81-2];

- cyclodextrin, ethyl-3-oxobutanoate (CAS No.: 152154-93-3];

- cyclodextrin, 3-oxobutanoate (CAS No.: 2135428-63-4);

- myristoyl pullulan acetoacetate.

According to a preferred embodiment, the compounds of formula (I) are chosen from raffinose acetoacetate, hydroxypropylcellulose acetoacetate, pullulan acetoacetate and myristoyl pullulan acetoacetate.

According to a preferred embodiment, the polysaccharides and/or oligosaccharides bearing acetoacetate functions are chosen from the compounds of formula (XI) and also the optical isomers thereof, the organic or mineral acid or base salts thereof, and the solvates thereof, such as hydrates, and preferably chosen from pullulan acetoacetate (CAS No.: 2762209-81- 2) and myristoyl pullulan acetoacetate. According to one embodiment variant, the polysaccharide(s) and/or oligosaccharide(s) bearing acetoacetate functions of formula (I) are obtained by (poly)condensation of n equivalents of dicarbonyl reagent with a polysaccharide Ri/XHR including n equivalents of nucleophilic functions -XH according to the following scheme:

in which scheme:

- R¹, R², R^a, R^b and n are as defined in formula (I) described above;

- R³ represents a hydrogen atom, a (Ci-C4)alkyl group, in particular methyl, ethyl, isobutyl, t-butyl, or an electrofugal group such as CHah, or HaRC-SCh- such as triflate, with Hal, which may be identical or different, representing a halogen atom; and

- X’ represents an oxygen or sulfur atom, preferably an oxygen atom.

Such a preparation process is notably described in patent application WO 2020026143, or in the publications “Synthesis and properties of cellulose acetoacetates”, Macromolecules (1995), 28(12), 4122-8, and “A facile method of functional derivatization based on starch acetoacetate”, Carbohydrate Polymers, 2022, 289, 119468.

According to another embodiment variant, the polysaccharide(s) and/or oligosaccharide(s) bearing acetoacetate functions of formula (I) are obtained by enzymatic esterification, as described in patent application US 6528644B 1, or in patent application US 2010/0003730, by (poly)condensation(s) of n equivalents of 2-oxetanone, 4-methylene reagent with an oligo/poly saccharide nucleophilic reagent PRO ,! including n equivalents of -OH nucleophilic functions according to the following scheme:

in which scheme R¹ and n are as defined in formula (I) described above.

According to another embodiment variant, the polysaccharide(s) and/or oligosaccharide(s) bearing acetoacetate functions of formula (I) are obtained by (poly)condensation(s) of n equivalents of propylenedioxy carbonyl reagent with an oligo/poly saccharide nucleophilic reagent R^XHR including n equivalents of nucleophilic functions -XH according to the following scheme:

in which scheme:

- R¹, R², R^a, R^b and n are as defined in formula (I) described above;

- R³ represents a hydrogen atom, a (Ci-C4)alkyl group, in particular methyl, ethyl, isobutyl, t-butyl, or an electrofugal group such as CHaR, or HaRC-SCh- such as triflate, with Hal, which may be identical or different, representing a halogen atom; and

- X’ represents an oxygen or sulfur atom, preferably an oxygen atom.

Such a preparation process is notably described in the publication “Acetoacetylation with 2,2,6-trimethyl-4H-l,3-dioxin-4-one: a convenient alternative to diketene”, Journal of Organic Chemistry (1985), 50(14), 2431-5.

According to preferred embodiment variant, the polysaccharide(s) and/or oligosaccharide(s) bearing acetoacetate functions of formula (I) are obtained by (poly)condensation(s) of n equivalents of propylenedioxy carbonyl reagent with an oligo/poly saccharide nucleophilic reagent R^x(OH)n including n equivalents of -OH nucleophilic functions according to the following scheme:

in which scheme:

- R¹, R², R^a and n are as defined previously in formula (I);

- R^b’ and R^c’, which may be identical or different, represent a hydrogen atom or a (Ci- C4) alkyl group.

Such a preparation process is notably described in the publications “Efficient and catalyst- free synthesis of cellulose acetoacetates”, Cellulose, 2018, 25 (9), 4919-4928, “2,2,6- trimethyl-4H-l,3-dioxin-4-one: a convenient alternative to diketene”, Journal of Organic Chemistry 50(14), 2431-5, (1985), “Acetoacetylation of O-(hydroxypropyl)cellulose by 2,2,6-trimethyl-4H-l,3-dioxin-4-one”, Carbohydrate Research 156, 232-5, (1986), or in patent applications WO 97/40074 and WO 93/03063.

According to a preferred embodiment of the invention, the compounds of formula (I) are prepared by reacting a polysaccharide with n equivalents of ester R2-C(O)-C(Ra)(Rb)-C(O)- O-tBu in a polar aprotic solvent such as DMSO or DMF, preferably DMSO, at a temperature of between 25°C and 190°C preferably from 50°C to 130°C, and preferably at atmospheric pressure. The preparation process is, for example, that described in the scientific article “A facile method of functional derivatization based on starch acetoacetate”, Carbohydrate Polymers, 289, 119468 (2022).

The polysaccharide(s) and/or oligosaccharide(s) bearing acetoacetate functions of formula (I) and also the optical and geometrical isomers thereof, the organic or mineral acid or base salts thereof, and the solvates thereof as defined previously, are preferably present in a content ranging from 1% to 30% by weight, in particular from 2% to 25% by weight, more particularly from 4% to 22% by weight, relative to the total weight of the composition containing them.

Another subject of the invention is the compound myristoyl pullulan acetoacetate, the optical and geometrical isomers thereof, the salts thereof with an organic or mineral acid or base, and/or the solvates thereof, such as hydrates, of formula:

in which formula:

- m is as defined previously;

- R¹¹ , which may be identical or different, represents a hydrogen atom or a linear or branched, preferably linear, (Cio-Ci6)alkyl group, such as C13H27, or a linear or branched, preferably linear, (Cio-Ci6)alkylcarbonyl group, such as Ci3H27-C(O)-, or a group R⁹ as defined previously; it being understood that at least one, preferably at least two, group(s) R¹¹, and at least one (Cio-Ci6)alkyl or (Cio-Ci6)alkylcarbonyl group, such as C13H27 orCi3H27-C(O)-, are present in the above compound myristoyl pullulan acetoacetate. Another subject of the invention is a cosmetic composition comprising at least one myristoyl pullulan acetoacetate compound as defined above.

According to a particular embodiment of the invention, composition “Cl” as defined previously is an aqueous composition.

CROSSLINKING AGENT

According to a particular embodiment, the treatment process according to the invention as described previously comprises the application to keratin materials (i) of at least one or more compounds of formula (I) and also the optical and geometrical isomers thereof, the acid or base salts thereof, and/or the solvates thereof, and (ii) of at least one crosslinking agent.

For the purposes of the invention, the term “crosslinking agent”, also termed “R”, denotes a compound that is capable of establishing with at least one acetoacetate function of the compound(s) of formula (I) used in the treatment process according to the invention:

- at least one covalent bond,

- at least one donor-acceptor (dative) bond, and/or

- at least one coordination bond, and thus of crosslinking this or these compounds.

Preferably, the term “crosslinking agent”, also termed “R”, refers to a compound that is capable of establishing at least one covalent bond with an acetoacetate function of the compound(s) of formula (I) used in the treatment process according to the invention and thus of crosslinking this or these compounds.

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

Compositions “C2”, “C3” and “C4” as defined previously may contain at least one crosslinking agent. The compositions of the invention may comprise a fatty phase, an aqueous phase or may be in the form of a direct or inverse emulsion. Composition “C4” may be an aqueous composition. Composition “C2” may be an aqueous composition.

According to one aspect, the treatment process of the invention uses a composition termed “C3”, notably a cosmetic composition for keratin materials, in particular for caring for and/or making up the skin, the lips, the eyelashes and/or the eyebrows and/or for caring for, styling and/or colouring keratin fibres, preferably the hair, comprising i) at least one compound of formula (I) and also the optical and geometrical isomers thereof, the acid or base salts thereof, and/or the solvates thereof, as defined previously, ii) at least one crosslinking agent, iv) at least one cosmetic active agent, notably as defined previously, in particular at least one dyestuff, more particularly at least one pigment, and optionally iii) water.

The crosslinking agent(s) 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, more particularly from 1% to 20% by weight, even more particularly from 1% to 10% relative to the total weight of the composition containing same.

In particular, the crosslinking agent(s) and the compound(s) of formula (I) are preferably present in a mass content ranging from 1% to 35% by weight, relative to the total weight of the composition comprising them.

More precisely, the crosslinking agent(s) R that are suitable for use in the invention may be chosen from compounds bearing amine, thiol, acrylate and/or carbonyl functions, such as a ketone or aldehyde function. A crosslinking agent R may also denote a metal alkoxide.

Thus, according to a particular embodiment, the crosslinking agent R is chosen from (poly)amine, (poly)thiol, (poly)carbonyl, (poly)acrylate and metal alkoxide compounds and mixtures thereof, preferably chosen from (poly)amine, (poly)thiol and (poly)acrylate compounds and mixtures thereof, and more preferentially chosen from (poly)amine, (poly)thiol compounds and mixtures thereof.

The term “(poly)amine, (poly)thiol, (poly)carbonyl and (poly)acrylate compounds” is intended to denote compounds including at least one primary or secondary amine, thiol, carbonyl (such as a ketone or aldehyde function) or acrylate function, respectively.

The metal alkoxide compounds are defined hereinbelow.

A) (Poly)amine compounds

According to a preferred embodiment, the crosslinking agent R is chosen from (poly)amine compounds.

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

The (poly)amine compound may be a compound comprising from 2 to 20 carbon atoms, notably a nonpolymeric compound; they may be acyclic or cyclic, linear or branched, saturated or unsaturated, conjugated or non-conjugated, aromatic or non-aromatic, optionally interrupted with one or more heteroatoms chosen from O, S, Si(R’)2, N(R”) preferably O, Si(R’)2, or combinations thereof such as -Si(R’)2-O- or -O-Si(R’)2-, with R’, which may be 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.

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

(Poly)amine compounds that may be mentioned in particular include N-methyl-1,3- diaminopropane, N-propyl- 1,3 -diaminopropane, N-isopropyl- 1,3 -diaminopropane, N- cyclohexyl- 1 ,3-diaminopropane, 2-(3-aminopropylamino)ethanol, 3-(2- aminoethyljaminopropylamine, bis(3-aminopropyl)amine, methylbis(3- aminopropyljamine, N-(3-aminopropyl)-l,4-diaminobutane, N,N- dimethyldipropylenetriamine, 1 ,2-bis(3-aminopropylamino)ethane, N,N’ -bis(3- aminopropyl)-l,3-propanediamine, ethylenediamine, 1,3 -propylenediamine, 1,4- butylenediamine, lysine, cystamine, xylenediamine, tris(2-aminoethyl)amine, 1,3- bis(aminomethyl)cyclohexane, 1 ,4-bis(aminomethyl)cyclohexane, diaminopropanol, 4,7,10-trioxa-l,13-tridecanediamine, spermidine and C36-alkylenediamines (Priamine™ 1071, 1073, 1074, 1075, respectively), preferably spermidine.

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

The (poly)amine compound(s) may be chosen from amino alkoxysilanes, notably of formula R’iSi(OR’2)z(R’3)x in which:

- R’ I is a linear or branched, saturated or unsaturated, cyclic or acyclic Ci-Ce hydrocarbon-based chain substituted with a group chosen from primary amine groups NH2 or secondary amine groups -N(H)R with R representing a C1-C4 alkyl, an aryl or a benzyl substituted with an amino group or with a C1-C4 aminoalkyl group; R’i may be interrupted in its chain with a heteroatom (O, S, NH) or a carbonyl group (CO), R’ 1 being linked to the silicon atom directly via a carbon atom,

- R’2 and R’3, which may be identical or different, represent a linear or branched (Ci- Ce) alkyl group,

- z denotes an integer ranging from 1 to 3, and - x denotes an integer ranging from 0 to 2, with z + x = 3.

In particular, R’i is an acyclic chain. Preferably, R’i is a linear or branched, saturated or unsaturated Ci-Ce hydrocarbon-based chain substituted with an amine NH2 or -N(H)R group, with R representing a Ci-Ce alkyl, a C3-C6 cycloalkyl or a Cf> aromatic group. More preferentially, R’i is a saturated linear Ci-Ce hydrocarbon-based chain substituted with an amine group NH2. Even more preferentially, R’ 1 is a saturated linear C2-C4 hydrocarbonbased chain substituted with an amine group NH2.

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

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 preferentially R’3 represents methyl or ethyl groups. Preferably, z is equal to 3.

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

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

The (poly)amine compound may also be chosen from amino polymers, notably having a weight-average molecular weight ranging from 500 g.mol ¹ to 1 000000 g.moT¹, preferably ranging from 500 g.mol ¹ to 500000 g.mol ¹, and preferentially ranging from 500 g.mol ¹ to 100000 g.mol ¹.

According to a particular embodiment of the invention, the (poly)amine compounds are monoamine compounds and are chosen from poly dialkylsiloxanes notably of formula (IV): H₂N-ALK-Si(R’2)(R’3)-O-[ Si(R’₂)(R’3)-O]_n- Si(R’₂)(R’₃)-R’4 (IV) in which formula (IV): - Aik represents a (C1-C4) alkylene group which is linear or branched, preferably linear, such as propylene,

- R’2 and R’3, which may be identical or different, preferably identical, represent a (Ci- C4)alkyl group, such as methyl, and

- R’4 represents a linear or branched (Ci-C6)alkyl group, preferably C4, such as n-butyl, n represents an integer greater than or equal to 2, preferably the value of n is such that the weight-average molecular weight of the polydimethylsiloxane ranges from 500 to 3000 g. mol ¹. As examples of polydimethylsiloxanes (V), mention may be made of the products sold under the names MCR-A11 and MCR-A12 by the company Gelest.

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

More particularly, they are chosen from the compounds of formula (V) or (VI):

. ALK[(O-ALK’)_m-NH₂]₂ (V) or

. H2N-ALK-Si(R’)2-[O-Si(R’)2]m-O-Si(R)2-ALK’-NH2 (VI) in which formulae (V) and (VI):

- ALK and ALK’, which may be identical or different, represent a linear or branched (Ci- C6)alkylene group, preferably a linear group such as propylene,

- R’, which may be identical or different, represents a (Ci-C4)alkyl group such as methyl,

- m represents an integer greater than or equal to 0; preferably, the value of m is such that the weight- average molecular weight of compound (V) or (VI) ranges from 500 g.mol ¹ to 55 000 g.mol ¹.

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

The (poly)amines compounds that are diamines are particularly polyether diamines notably of formula H2N-ALK-O-[ALK’-O]_m-ALK”-NH2 with ALK, ALK’ and ALK”, which may be identical or different, representing a linear or branched (Ci-C6))alkylene group, and m representing an integer greater than or equal to 0, such as 4,7,10-trioxa-l,13- tridecanediamine or the compounds known under the reference Jeffamine from the company Hunstman, and more particularly a,co-diamino polyethylene glycol and/or polypropylene glycol (with an amine function at the end of the chain) such as the products sold under the names Jeffamine D-230, D-400, D-2000, D-4000, ED-600, ED-9000 and ED-2003.

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

As (poly)amine compounds that are triamine compounds, mention may be made in particular of polyether triamines, and notably a,co-diamino polyethylene glycol and/or polypropylene glycol (with an amine function at the end of the chain) such as the products sold under the names Jeffamine T-403.

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

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

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

According to this variant, the (poly)amine compound(s) are chosen in particular from poly((C2-C5)alkyleneimines), and preferably polyethylenimines and polypropyleneimines, notably poly(ethyleneimine), in particular the product sold under reference 408700 by the company Aldrich Chemical or under the trade name Lupasol by BASF, notably with a molecular weight of between 1200 and 25 000; poly (allylamine), in particular the product sold under reference 479136 by the company Aldrich Chemical; polyvinylamines and copolymers thereof, notably with vinylamides, in particular vinylamine/vinylformamide copolymers such as those sold under the name Lupamin® 9030 by the company BASF; polyamino acids containing NH2 groups, such as polylysine, in particular the product sold by the company JNC Corporation (formerly Chisso); amino dextran, in particular the product sold by the company CarboMer Inc; amino polyvinyl alcohol, in particular the product sold by the company CarboMer Inc; acrylamido(Ci-C6)alkylamine-based copolymers, notably acrylamidopropylamine-based copolymers; and poly(D-glucosamine), for example sold under the reference Kionutrime CSG® by the company Kytozyme.

According to a particular embodiment, the polydimethylsiloxanes comprising primary amine groups at the end of the chain and/or on side chains are chosen from the compounds of formula (VII) below: Ra-Si(R_b)(Rc)-O-[Si(Rb)(Rc)-O]_m-[Si(ALK¹-NH₂)(Ra)-O]_n-Si(Rb)(Rc)-Ra (VII) in which formula (VII):

R_a, which may be identical or different, represents a hydroxyl or (Ci-C4)alkyl group,

- Rb and R_c, which may be identical or different, preferably identical, represent a (Ci-C4)alkyl group, such as methyl,

- ALK¹ represents a linear or branched (Ci-Ce) alkylene group, optionally interrupted with an N(H) group,

- m and n are integers greater than or equal to 1 ; preferably, m and n are such that the weightaverage molecular mass of the compound of formula (VII) ranges from 1000 g.mol ¹ to 500000 g.mol ¹.

According to a preferred variant, formula (VII) is such that R_a, Rb and R_c represent a methyl group, ALK¹ represents a propylene group, n and m are such that the weight-average molecular weight of the polydimethylsiloxane ranges from 1000 g.mol ¹ to 55 000 g.mol ¹. As examples of polydimethylsiloxanes of formula (VI), mention may be made of those sold under the names AMS-132, AMS-152, AMS-162, AMS-163, AMS-191 and AMS-1203 by the company Gelest.

According to another variant, formula (VII) is such that R_a represents a hydroxyl or (Ci- C4)alkyl group, such as methyl, ALK¹ represents a (Cs-C6)alkylene group substituted with 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.mol ¹ to 500 000 g.mol ¹.

As amine polymer, mention may also be made of a,co-diamino polytetrahydrofurans (or polytetramethylene glycol) and a,co-diamino polybutadienes.

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

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

More preferentially, the composition comprises a crosslinking agent chosen from chitosans, aminoalkoxysilanes and polydialkylsiloxanes comprising primary amine groups at the end of the chain or on side chains such as amodimethicones, and even more preferentially chosen from poly(D-glucosamine), 3 -aminopropyltriethoxy silane (APTES), 3- aminoethyltriethoxy silane (AETES), 3-aminopropylmethyldiethoxysilane, N-(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

According to a preferred embodiment, the crosslinking agent R is chosen from (poly)thiol compounds, also known as “(poly)mercapto” compounds.

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

In a preferred embodiment, the (poly)thiol compound is silicon-based, i.e. it includes one or more thiol groups and it also includes at least one siloxane chain.

In a particular embodiment, the (poly)thiol compound is inorganic. Mention may be made, for example, of polythiol silicones.

The (poly)thiol compound may in particular be chosen from non-polymeric (poly)thiol compounds.

For the purposes of the present invention, the term “non-polymeric compounds” means compounds which are not directly obtained via a monomer polymerization reaction. According to one embodiment of the invention, the (poly)thiol compound(s) are organic, non-polymeric and of formula (VIII) below and also the solvates thereof such as hydrates: L(SH)_q (VIII) in which formula (VIII): - q denotes an integer greater than or equal to 2; preferably, q is between 2 and 10 and preferably between 2 and 5 inclusive;

- L denotes a linear or branched, saturated or unsaturated, or (hetero)cyclic, saturated or unsaturated, 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; L being optionally interrupted and/or terminated with one or more heteroatoms or groups chosen from O, S, N, Si, C(X), and combinations thereof such as -O-, -O-C(X)-, -N(R)-C(X)-, -Si(R_c)(Rd)-O- with R representing a hydrogen atom or a (Ci-Ce/alkyl group such as methyl; and/or L being optionally substituted with one or more groups chosen from: -N(R_a)Rb and -(X’)a-C(X)-(X”)b-R_a; with X, X’ and X”, which may be identical or different, representing an oxygen or sulfur atom, or a group N(Rb); a and b being 0 or 1, preferably the sum of a + b being 1; R_a and Rb, which may be identical or different, represent a hydrogen atom or a (Ci-Ce/alkyl or aryl(Ci-C4)alkyl group, such as benzyl, preferably R_a and Rb represent a hydrogen atom; and R_c and Rd, which may be identical or different, represent a (Ci-Ce/alkyl, aryl(Ci-C4)alkyl or (Ci-Cejalkoxy group.

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

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

The (poly)thiol compounds that are suitable for use in the invention are preferably dithiol compounds.

Preferably, L denotes a Cs-Cis multivalent radical, which is notably linear. Preferentially, the liposoluble polythiol is a notably linear Cs-Cis dithiol. Preferably, the Cs-Cis chain is a hydrocarbon-based chain, i.e. formed from carbon and hydrogen. In particular, the liposoluble polythiol is a linear Cs-Ci6 and notably C10-C14 dithiol. As (poly)thiol compounds of formula (VII), mention may be made more particularly of 1,8-octanedithiol, 1,10-decanedithiol, 1,12-dodecanedithiol, 1,14-tetradecanedithiol, 1,16-hexadecanedithiol and 1,18-octadecanedithiol. Use is preferably made of 1,10-decanedithiol, 1,12- dodecanedithiol and/or 1,14-tetradecanedithiol, preferentially 1,12 -dodecanedithiol. According to another particular embodiment of the invention, the (poly)thiol compound(s) are chosen from thiolated alkoxy siloxanes, such as those of formula (VIII’) below: R’i-Si(OR’2)z(R’₃)x (VIII’) in which formula (VIII’):

- R’ I is a linear or branched, saturated or unsaturated, cyclic or acyclic C1-C12 hydrocarbonbased chain substituted with one or more groups chosen from thiol groups; and aryl, aryloxy, arylthio, arylamino, the aryl group being substituted with one or more thiol groups, or thiol(Ci-C6) alkyl, preferably thiol(Ci-C6)alkyl; and R’i is optionally interrupted in its hydrocarbon-based chain with one or more heteroatoms such as O, S, N, a carbonyl group C(O), or a combination thereof such as ester -C(O)-O-, or amide -C(O)-N(H)-, R’i being bonded to the silicon atom directly via a carbon atom,

- R’2 and R’3, which may be identical or different, represent a linear or branched alkyl group comprising from 1 to 6 carbon atoms, preferably from 1 to 4 carbon atoms, such as methyl,

- z denotes an integer ranging from 1 to 3, and

- x denotes an integer ranging from 0 to 2, with z + x = 3.

Preferably, R’2 represents a linear or branched, preferably linear, alkyl group comprising from 1 to 4 carbon atoms, such as ethyl.

Preferably, R’3 represents a linear or branched, preferably linear, alkyl group comprising from 1 to 4 carbon atoms, such as methyl or ethyl.

Preferably, R’i is an acyclic chain, in particular R’i is a linear or branched, saturated or unsaturated, preferably saturated, Ci-Ce hydrocarbon-based chain substituted with one or more thiol groups, preferably substituted with one thiol group.

Preferably, R’i is a saturated linear Ci-Ce hydrocarbon-based chain substituted with a thiol group, and R’2 represents an alkyl group comprising from 1 to 4 carbon atoms.

Preferably, R’3 represents an alkyl group comprising from 1 to 4 carbon atoms.

Preferably, z is equal to 3.

According to a more particular embodiment of the invention, the thiolated alkoxy siloxanes are chosen from those of formula (IX) below:

(R¹O)(R²)(R³)Si-[CH(R⁴)]t-[N(R’⁴)-L¹]_p-SH (IX) in which formula (IX):

- p is 0 or 1 ; - 1 is an integer between 1 and 4, preferably 2;

- R¹ represents a (Ci-C6)alkyl radical;

- R² and R³, which may be identical or different, preferably identical, are chosen from a (Ci- Ce)alkyl group, in particular a C1-C4 alkyl group, such as methyl, and a (Ci-Ce/alkoxy group, in particular a (Ci-C4)alkoxy group, such as methoxy;

- R⁴ and R’⁴, which may be identical or different, represent a hydrogen atom or a (Ci-C6)alkyl group, such as methyl;

- L¹ represents a divalent, saturated, linear or branched C1-C20 hydrocarbon-based radical.

According to a particular embodiment of the invention, the thiolated alkoxysiloxanes are chosen from those of formula (IX’) below: (R’¹O)(R’²)(R’³)Si-CH(R⁴)-CH(R⁵)-(L²)_q-SH (IX’) in which formula (IX’):

- q is equal to 0 or 1 ;

- X represents an oxygen or sulfur atom, preferably a sulfur atom;

- R’¹ denotes a (Ci-C6)alkyl radical;

- R’² and R’³, which may be identical or different, preferably identical, are chosen from a (Ci-C6)alkoxy group, in particular a C1-C4 alkoxy group, and a (Ci-C6)alkyl radical;

- R⁵ represents a hydrogen atom or a C1-C4 alkyl group optionally substituted with an amino, thiol or hydroxyl group;

- R⁴ represents a hydrogen atom or a C1-C4 alkyl group, in particular methyl;

- L² represents a linear or branched, saturated C1-C20 divalent hydrocarbon-based group, optionally interrupted with a heteroatom such as -N(H)-, and/or optionally substituted with one or more hydroxyl, thiol or amino groups.

Preferably, the thiolated alkoxysilane(s) are chosen from 4-(trimethoxy silyl)- 1 -butanol, 3- (trimethoxy silyl)- 1 -propanol, 3 -(triethoxy silyl)- 1 -propanol, 11 -(trimethoxy silyl)- 1- undecanethiol, 4-(trimethoxysilyl)-2-butanethiol, 2-(triethoxysilyl)ethanethiol, 3- (triethoxysilyl)-l -propanethiol, 2-(trimethoxysilyl)ethanethiol, 3-(trimethoxysilyl)-l- propanethiol and 3-(dimethoxymethylsilyl)-l-propanethiol.

More preferentially, the thiolated alkoxysilane(s) are chosen from 2- (triethoxysilyl)ethanethiol (18236-15-2) and 3 -(triethoxysilyl)-l -propanethiol (14814-09-6). According to a preferred embodiment of the invention, the (poly)thiol compound(s) are chosen from polymeric (poly)thiol compounds. The polymeric (poly)thiol compounds may be star, comb, brush and dendritic homopolymers or copolymers bearing thiol units. The polymers may be of natural origin such as polysaccharides or polypeptides, or of synthetic origin such as acrylic polymers, polyesters or polyglycols. The thiol units may be present as terminal or side groups.

Examples that may be mentioned include the polymers described in the following articles: Polymers containing groups of biological activity, C.G. Overberger et al., Polytechnic Institute of Brooklyn, http://pac.iupac.org/publications/pac/pdf/1962/pdf/0402x0521.pdf; EP 1 247 515 A2; U.S. 3 676 440; and EP 1 572 778.

The polymeric (poly)thiol compounds of the invention are preferably organic and/or silicone compounds, more preferentially of formula (X):

POLY(SH)_q (X) in which formula (X):

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

- POLY denotes a polymer-based radical, preferably carbon-based or silicone-based; POLY being optionally interrupted with one or more heteroatoms or groups chosen from O, S, N, Si, C(X), and combinations thereof such as -O-, -O-C(X)-, -N(R)-C(X)-, -Si(R_c)(Rd)-O- with R representing a hydrogen atom or a (C i-CeJalkyl group such as methyl; and/or POLY being optionally substituted with one or more halogen atoms, or a group chosen from R_a(Rb)N- and -(X’)a-C(X)-(X”)b-R_a; X, X’ and X”, which may be identical or different, represent an oxygen or sulfur atom or a group N(Rb); a and b being 0 or 1, preferably the sum of a + b being 1; R_a and Rb, which may be identical or different, represent a hydrogen atom or a (Ci- Cio)alkyl or aryl(Ci-C4)alkyl group, such as benzyl, preferably R_a and Rb represent a hydrogen atom; and R_c and Rd, which may be identical or different, represent a (Ci-Cio)alkyl, aryl(Ci-C4)alkyl or (Ci-Cio)alkoxy group.

The methods for preparing the polymeric (poly)thiol compounds used according to the invention are known to those skilled in the art; several methods are reported hereinbelow in a non-limiting manner. The polymeric (poly)thiol compounds used according to the invention may be obtained by polymerization or polycondensation of monomer units bearing thiol or protected thiol functions, optionally as a copolymerization or co -polycondensation of monomer units free of thiol or protected thiol functions.

According to one embodiment of the invention, the polymeric (poly)thiol compounds used according to the invention are polymers which are soluble in cosmetic media, particularly in aqueous or aqueous -alcoholic media. They are more preferentially obtained from amino polymers and the ammonium salts thereof or from poly hydroxylated polymers.

According to another embodiment of the invention, the thiolated polymers used according to the invention are polymers that are soluble in lipophilic media.

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-based and/or silicon-based, preferably silicon-based, polymeric radical, POLY also possibly containing one or more heteroatoms chosen from O, N or S, and/or one or more functions chosen from (thio)ester, (thio)ketone, (thio)amide, (thio)urea and (thio)carbamate functions, and/or possibly being substituted with one or more linear or branched (Ci-Cio)alkyl or linear or branched (Ci-Cio)alkoxy groups, it being understood that when POLY is substituted, the thiol functions may be borne by the substituent(s).

The weight-average molecular weight of the polythiol polymer compounds, such as those of formula (X), is generally between 500 and 400 000 g.moT¹, preferably between 500 and 150000 g.moT¹.

According to a particular embodiment of the invention, the polythiolated compounds are chosen polyorganosiloxanes including thiol groups on end chains, such as those of formula (XI) below:

HS-L⁴-Si(R^a)(R^b)-O-[Si(R^a)(R^b)-O]_n-Si(R^a)(R^b)-L⁵-SH (XI) in which formula (XI):

- R^a and R^b, which may be identical or different, preferably identical, represent a group from among: (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 (Ci-C4)alkyl such as methyl;

- n represents an integer greater than or equal to 1 and more particularly the value of n is such that the weight- average molecular weight of the silicone ranges from 500 to 55 000 g.moT¹; in particular, n is an integer ranging from 1 to 100, preferably ranging from 5 to 50 and preferentially ranging from 10 to 30, and

- L⁴ and L⁵, which may be identical or different, preferably identical, represent a linear or branched, saturated or unsaturated, optionally cyclic hydrocarbon-based chain comprising from 1 to 100 carbon atoms, optionally interrupted with one or more heteroatoms such as oxygen, sulfur or nitrogen, in particular oxygen, and in particular represent a covalent bond or a (Ci-C6)alkylene, (Ci-C6)alkylenoxy, oxy(Ci-C6)alkylene, (Ci-C6)alkylenoxy(Ci- C6)alkylene, (Ci-C6)alkylenoxy(Ci-C6)alkylenoxy or oxy(Ci-C6)alkylenoxy(Ci-C6)alkylene group, preferably a (Ci-C6)alkylene, (Ci-C6)alkylenoxy, oxy(Ci-C6)alkylene or (Ci- Ce) alky lenoxy (C i -Ce) alkylene group .

Preferentially, the (poly)thiol compounds are polythiol polyorganosiloxanes, more preferentially polythiol poly dimethylsiloxanes, notably chosen from those of formula (XII): HS-L⁴-Si(CH3)2-O-[Si(CH3)2-O]_n-Si(CH3)₂-L⁵-SH (XII) in which formula (XII):

- L⁴ and L⁵ are as defined previously in formula (IX), in particular L⁴ and L⁵ represent a (Ci- C6)alkylene, (Ci-C6)alkylenoxy, oxy(Ci-C6)alkylene or (Ci-C6)alkylenoxy(Ci-C6)alkylene group, more preferentially a divalent group chosen from -R2-, -O-R2-, -R2-O- and -R2- O-R2-, preferably -R2-O-R2-, with R2 representing a linear or branched, preferably linear, (C2-C6)alkylene group, such as ethylene or n-propylene, preferably n-propylene; and

- n is as defined in formula (XI).

As polythiolated compounds of formula (XII), mention may be made of mercaptosiloxanes or thiolated siloxanes in which the thiol functions are at the chain ends, sold by the company Shin-Etsu under the reference X-22-167B, and mercaptosiloxane in which the mercapto functions are pendent, sold by the company Shin-Etsu under the reference KF-2001, or polydimethylsiloxanes in which the thiol functions are at the chain ends, via thio-n-propyl, 80-120 groups, sold by the company Gelest under the name DMS-SM 21.

Preferentially, the polythiolated compounds are chosen polyorganosiloxanes including thiol groups on side chains, such as those of formula (XIII): R^a-Si(R^b)(R^d)-O-[Si(R^a)(R^b)-O]_m-[Si(R^b)(ALKi-SH)-O]ii-Si(R^b)(R^d)-R^a (XIII) in which formula (XIII):

- R^a and R^b are as defined in formula (XI) and R^d is as defined for R^a and R^b, preferably R^a, R^b and R^d, which are identical, represent a (Ci-C6)alkyl group, such as methyl;

- R^d may also represent a (Ci-C6)alkyl group substituted with a (Ci-C4)alkylamino or amino or thiol group, preferably (Ci-C4)alkyl such as methyl;

- ALKi represents a linear or branched, optionally cyclic, saturated or unsaturated divalent hydrocarbon-based chain comprising from 1 to 100 carbon atoms, optionally interrupted with 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 combinations thereof such as -O- , -O-C(O)- or -C(O)-O-; preferably, ALKi represents a (Ci-C6)alkylene and more preferentially (Ci-C4)alkylene group such as propylene;

- n and m, which may be identical or different, represent an integer greater than 2 and more particularly the values of m and n are such that the weight- average molecular weight of said polyorganosiloxane is between 1000 and 55 000 g.mol ¹.

As examples of polythiolated compounds of formula (XIII), mention may be made of those sold by the company Genesee Polymers under the names GP-367, GP-71-SS, GP-800 and GP-710s, preferably GP-367, sold by the company Genesee Polymers.

The polythiolated compounds are notably polydimethylsiloxanes including at least two thiol groups, for instance the 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.

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 thiolated PAMAM dendrimers.

Preferably, the (poly)thiol compounds used according to the invention are chosen from polydiallylsiloxanes, notably polydimethylsiloxanes, including at least two thiol groups such as those of formula (XIII).

C) (Poly)acrylate compounds

According to a particular embodiment, the crosslinking agent is a (poly)acrylate compound. The term “(poly)acrylate” means a compound which comprises at least one acrylate ester group H2C=C(R^e)-C(0)-Y- with R^e representing a hydrogen atom or a (Ci-C4)alkyl group, such as methyl, preferably R^e representing a hydrogen atom, and Y representing an oxygen atom or an amino group -N(H)-, preferably an oxygen atom.

More particularly, the (poly)acrylate(s) of the invention are of formula (XIV): L[-Y-C(0)-C(R^e)=CH₂]_q (XIV) in which formula (XIV) q and L are as defined in formula (VIII), Y and R^e being as defined previously, preferably Y = O and R^e = H.

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

According to a particular embodiment, the (poly)acrylate compounds are chosen from polyorganosiloxanes including at least one acrylate group on the side chain, such as those of formula (XV): R^a-Si(R^b)(R^d)-O-[Si(R^a)(R^b)-O]_m-[Si(R^b)(ALKi-Y-C(O)-C(R^e)=CH₂)-O]_n-Si(R^b)(R^d)-R^a (XV) in which formula (XV):

- R^a, R^b and R^d are as defined for formula (XIII), preferably R^a, R^b and R^d represent a (Ci- C6)alkyl group, such as methyl,

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

- Y is as defined previously, and is preferably an oxygen atom.

More particularly, the (poly)acrylate compound may be chosen from 1,3 -butanediol diacrylate, 1,4-butanediol diacrylate, bis(trimethylolpropane) tetraacrylate, glyceryl 1,3- diglycerolate diacrylate, glyceryl propoxylate (1PO/OH) triacrylate, 1,6-hexanediol diacrylate, 1,6-hexanediol ethoxylate diacrylate, hydroxypivalyl hydroxypivalate, neopentyl glycol diacrylate, neopentyl glycol propoxylate (1PO/OH) diacrylate, pentaery thrityl tetraacrylate, pentaerythrityl triacrylate, poly(propylene glycol) diacrylate, tricyclo[5.2.1.02,6]decanedimethanol diacrylate, trimethylolpropane ethoxylate (1EO/OH) methyl ether diacrylate, trimethylolpropane propoxylate triacrylate, trimethylolpropane triacrylate, trimethylolpropane trimethacrylate, tri(propylene glycol) diacrylate, and tris[2- (acryloyloxy)ethyl] isocyanurate.

The (poly)acrylate compound may also be chosen from N,N’ -methylenebisacrylamide. According to this embodiment, the (poly)acrylate compound is combined in its implementation with an amine catalyst as described, for example, in 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 (l,4-diazabicyclo[2.2.2]octane) and DBN (1,5- diazabicyclo[4.3.0]non-5-ene), more preferentially chosen from DBU (1,8- diazabicyclo[5.4.0]undec-7-ene), DABCO (l,4-diazabicyclo[2.2.2]octane) and 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 particularly, the (poly)acrylate compounds are chosen from those of formula (XIV), notably trimethylolpropane triacrylate, and those of formula (XV), notably dimethylsiloxane and acryloxypropyl)methylsiloxane copolymers.

D) Metal alkoxides

According to a particular embodiment, the crosslinking agent R is a compound chosen from the metal alkoxides of formulae (XIVa), (XlVb), (XIVc) and (XXIVd) below and mixtures thereof:

. M-(ORl)_n (XIVa)

. R-M-(ORi)_n-i (XlVb)

. (RiO)n-i-M-R”-M’-(ORi’)n -i (XIVc)

. R-M(R’)-(0Ri)_n-2 (XXIVd) in which formulae (XIVa), (XlVb), (XIVc) and (XIV_d):

- M and M’, which may be identical or different, represent an atom chosen from alkaline- earth metals, transition metals, metals of the lanthanide family, 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;

- n and n’ respectively represent the valencies of the atoms represented by M and M’;

- Ri and Rf, which may be identical or different, represent a linear or branched, saturated or unsaturated hydrocarbon-based group containing from 1 to 30 carbon atoms, preferably from 1 to 6 carbon atoms, said hydrocarbon-based group being optionally interrupted with 1 to 20 heteroatoms chosen from O, N, S and P, notably O or N; and/or said hydrocarbonbased group being optionally substituted with one or more hydroxyl or carbonyl groups;

- R and R’, which may be identical or different, represent a hydrogen atom or a linear, branched, acyclic or cyclic, saturated or unsaturated hydrocarbon-based group containing from 1 to 30 carbon atoms, preferably from 2 to 20 carbon atoms, optionally interrupted with 1 to 20 heteroatoms chosen from O, N, S and/or P, notably O or N, and/or said hydrocarbonbased group being optionally substituted with one or more hydroxyl or carbonyl groups; - R” represents -0-, -N(R2)-, -S- or a linear, cyclic or branched, saturated or unsaturated divalent hydrocarbon-based group containing from 1 to 30 carbon atoms, preferably from 2 to 20 carbon atoms, optionally interrupted with 1 to 20 heteroatoms chosen from O, N, S and P, notably O or N, with R2 representing a linear, cyclic or branched, saturated or unsaturated hydrocarbon-based group containing from 1 to 30 carbon atoms, preferably from 2 to 20 carbon atoms.

Preferably, M and M’, which may be identical or different, represent an atom chosen from transition metals such as titanium or zirconium or alkaline-earth metals such as magnesium, more preferentially chosen from transition metals such as titanium or zirconium, even more preferentially titanium.

Preferably, the organometallic compound(s) are chosen from the alkoxides of formula (XIVa) as defined previously. According to this preferred embodiment, the organometallic compound(s) are more particularly chosen from the alkoxides of formula (XIVa), in which M represents an atom chosen from transition metals, metals of the lanthanide family, posttransition metals, such as aluminium, tin, metalloids, such as boron, or alkaline-earth metals, such as magnesium or calcium; n represents the valency of the atom represented by M; Ri represents a saturated, linear or branched, hydrocarbon-based group containing from 1 to 30 carbon atoms, preferably from 1 to 6 carbon atoms.

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

According to an even more preferred embodiment, the organometallic compound(s) are chosen from zirconium ethoxide (Zr(OC2Hs)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(OC2Hs)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), titanium 2- ethylhexyloxide (Ti(OCH2CH(C2Hs)(CH2)3CH3)4), and mixtures thereof, more preferentially chosen from zirconium propoxide, titanium propoxide, titanium butoxide and mixtures thereof.

More preferentially, the crosslinking agent R is a compound of formula (XXIVa) preferably in which M represents an atom chosen from transition metals, notably titanium such as titanium butoxide.

E) (Poly)carbonyl compounds

According to a particular embodiment, the crosslinking agent R is a (poly)carbonyl compound.

In particular, the (poly)carbonyl compound is chosen from terephthalaldehyde, 5,5- dimethyl-l,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-l,3,5-tricarboxaldehyde, and nonionic or anionic oxidized polysaccharides such as oxidized inulins, notably those of formula (II) as defined hereinbelow. In particular, the (poly)carbonyl compounds include a saturated or unsaturated, aromatic C5-C7 carbocycle, preferably aromatic, such as phenyl, or non-aromatic and saturated such as cyclohexyl, more preferentially unsaturated and aromatic, such as terephthaldehy de .

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

It is understood that the oxidized polysaccharides are different from the compounds of formula (I) in that they do not comprise any group as follows:

with R², R^a, R^b and X as defined in formula (I).

These anionic groups are preferably carboxyl or carboxylate groups. The nonionic or anionic oxidized polysaccharides according to the invention may be represented by formula (XX) below:

P-(CHO)_m (COOQ)n (XX) in which formula (XX):

- P represents a polysaccharide chain preferably consisting of monosaccharides comprising 5 carbon atoms or more than 5 carbon atoms, preferably 6 or more than 6 carbon atoms and more particularly 6 carbon atoms;

- Q is chosen from a hydrogen atom, the ions derived from an alkali metal or an alkaline- earth metal such as sodium or potassium, ammonia, organic amines such as monoethanolamine, diethanolamine, triethanolamine and 3-amino-l,2-propanediol and basic amino acids such as lysine, arginine, sarcosine, ornithine and citrulline;

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

- m is such that the degree of substitution of the polysaccharide with one or more aldehyde groups (DS(CHO)) is within the range from 0.001 to 2 and preferably from 0.005 to 1.5;

- n is such that the degree of substitution of the polysaccharide with one or more carboxylic groups (DS(COOX)) is within the range from 0 to 2 and preferably from 0.001 to 1.5.

The expression “degree of substitution DS(CHO) or DS(COOX) of the polysaccharides according to the invention” means the ratio between the number of carbons oxidized to give an aldehyde or carboxylic group for all the repeating units and the number of elementary monosaccharides (even opened by preoxidation) constituting the polysaccharide. The groups CHO and COOX may be obtained during the oxidation of certain carbon atoms, for example on the carbon atoms 2, 3 or 6, of a saccharide unit containing 6 carbon atoms.

Preferably, the oxidation may take place on carbons 2 and 3, more particularly of 0.01% to 75% by number, and preferably of 0.1% to 50% by number of the rings that may have been opened.

The polysaccharide chain, represented by P, is preferably chosen from celluloses, starches, maltodextrins, guar gums, xanthan gums, pullulan gums, agar-agar gums, carrageenan gums, gellan gums, acacia gums, polyxylans and tragacanth gums, and derivatives thereof.

The term “derivative” means the compounds obtained by chemical modification of the mentioned compounds. They may be esters, amides or ethers of said compounds.

The oxidation may take place 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).

Another oxidation process is described in the article “Water soluble oxidized starches by peroxide reaction extrusion” Industrial Crops and Products 7, R.E. Wing, J.L. Willet, 45-52 (1997).

According to this embodiment, the (poly)carbonyl compound is combined 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 (l,4-diazabicyclo[2.2.2]octane) and DBN (1,5- diazabicyclo[4.3.0]non-5-ene), more preferentially chosen from DBU (1,8- diazabicyclo[5.4.0]undec-7-ene), DABCO (l,4-diazabicyclo[2.2.2]octane) and 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).

According to a preferred embodiment, the crosslinking agent is chosen from (poly)amine compounds A), (poly)thiol compounds B) and (poly)acrylate compounds C), and preferably from (poly)amine compounds A) and (poly)thiol compounds B).

In particular, said (poly)amine compounds A) are chosen from a) chitosans, such as polypglucosamine), b) polyether diamines, particularly polyethylene glycol a,co-diamine (bearing an amine function at the end of the chain), c) polyether triamines, such as poly etheramine (or Jeffamine), d) aminoalkoxysilanes, such as APTES, e) spermidine and f) polydialkylsiloxanes comprising primary amine groups at the end of the chain or on side chains, in particular polydimethylsiloxanes comprising primary amine groups, such as bis(3- aminopropyl) -terminated poly(dimethoxy siloxane) (PDMS-diNFE) and amodimethicones comprising amine groups on side chains, such as bis-cetearyl amodimethicone, notably the product sold by Momentive Performance Materials.

According to a preferred embodiment, said (poly)amine compounds A) are chosen from a) chitosans, such as poly(D-glucosamine), c) polyether triamines, such as polyetheramine (or Jeffamine), e) spermidine and f) polydialkylsiloxanes comprising primary amine groups at the end of the chain or on side chains, in particular poly dimethylsiloxanes comprising primary amine groups, such as bis(3-aminopropyl)-terminated poly(dimethoxysiloxane) (PDMS-diNPE) and amodimethicones comprising amine groups on side chains, such as bis- cetearyl amodimethicone, notably the product sold by Momentive Performance Materials. In particular, said (poly)thiol compounds B) are chosen from a) poly dialkylsiloxanes bearing thiol functions, and b) alkoxysilanes bearing thiol functions, and in particular are chosen from a) polydialkylsiloxanes bearing thiol functions, preferentially polydimethylsiloxanes comprising thiol groups on the side chain (such as mercaptopropyl), notably those of formula (XIII).

In particular, said (poly)acrylate C) compounds are chosen from those of formula (XIV), notably trimethylolpropane triacrylate, and those of formula (XV), notably copolymers of dimethylsiloxane and acryloxypropyl)methylsiloxane, preferably trimethylolpropane triacrylate.

According to a preferred embodiment, the crosslinking agent(s) are chosen from:

A) (poly)amine compounds chosen from: ia) chitosans such as poly(D-glucosamine), ib) polyether diamines, in particular polyethylene glycol a,co-diamines, bearing a chain-end amine function, ic) polyether triamines, in particular poly etheramines (or Jeff amine), id) aminoalkoxy silanes, in particular APTES, ie) spermidine, and if) polydialkylsiloxanes comprising primary amine groups at the end of the chain or on side chains, in particular polydimethylsiloxanes comprising primary amine groups, more particularly bis(3-aminopropyl)-terminated poly (dimethoxy siloxane) (PDMS-diNPE) and amodimethicones comprising amine groups on side chains, more particularly bis-cetearyl amodimethicone;

B) (poly)thiol compounds chosen from: iia) poly dialkylsiloxanes bearing thiol functions, and iib) alkoxysilanes bearing thiol functions, and in particular chosen from iia) polydialkylsiloxane compounds bearing thiol functions, preferably from polydimethylsiloxanes comprising thiol groups on the side chain, in particular mercaptopropyl, and more particularly chosen from the compounds of formula (XIII):

R^a-Si(R^b)(R^d)-O-[Si(R^a)(R^b)-O]m-[Si(R^b)(ALKi-SH)-O]n-Si(R^b)(R^d)-R^a (XIII) in which formula (XIII):

- R^a and R^b, which may be identical or different, preferably identical, represent a (Ci- C4)alkyl group, 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, preferably a (Ci-C4)alkyl group, more preferentially methyl,

- R^d represents a (Ci-C4)alkyl group, 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, an aryl(Ci-C4)alkoxy group, in particular benzoxy, or a (Ci-C6)alkyl group substituted with a (Ci-C4)alkylamino, amino or thiol group, and preferably a (Ci-C4)alkyl group, more preferentially methyl, and preferably R^a, R^b and R^d are identical and represent a (Ci-C6)alkyl group, more preferentially methyl,

- ALKi represents a linear or branched, optionally cyclic, saturated or unsaturated divalent hydrocarbon-based chain comprising from 1 to 100 carbon atoms, optionally interrupted with 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 combinations thereof, in particular -O-, -O-C(O)- or -C(O)-O-; preferably, ALKi represents a (Ci-C6)alkylene and more preferentially (C1-C4) alkylene group, even more preferentially propylene,

- n and m, which may be identical or different, represent an integer greater than 2, and in particular the values of m and n are such that the weight-average molecular weight of said polyorganosiloxane is between 1000 and 55 000 g.mol ¹; and

C) the (poly)acrylate compounds of formula (XIV):

L[-Y-C(O)-C(R^e)=CH₂]_q (XIV) in which formula (XIV):

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

- L denotes a linear or branched, saturated or unsaturated, or (hetero )cyclic, saturated or unsaturated, 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; L being optionally interrupted and/or terminated with one or more heteroatoms or groups chosen from O, S, N, Si, C(X), and combinations thereof, in particular -O-, -O-C(X)-, -N(R)-C(X)-, -Si(R_c)(Rd)-O- with R representing a hydrogen atom or a (Ci-C6)alkyl, in particular methyl; and/or L being optionally substituted with one or more groups chosen from: -N(R_a)Rb and -(X’)_a-C(X)-(X”)b-R_a; with X, X’ and X”, which may be identical or different, representing an oxygen or sulfur atom, or a group N(Rb); a and b being 0 or 1, preferably the sum of a + b being 1; R_a and Rb, which may be identical or different, represent a hydrogen atom, a (Ci-Cejalkyl group or an aryl(Ci-C4) alkyl group, in particular benzyl, preferably R_a and Rb represent a hydrogen atom, and R_c and Rd, which may be identical or different, represent a (C i -Cejalky 1, aryl(Ci-C4)alkyl or (Ci-Ce/alkoxy group,

- R^e represents a hydrogen atom or a (Ci-C4)alkyl group, in particular methyl; preferably, R^e represents a hydrogen atom, and

- Y represents an oxygen atom or an amino group -N(H)-, preferably an oxygen atom, preferably Y is an oxygen atom and R^e is a hydrogen atom, preferably L represents a di- or trivalent, preferably trivalent, hydrocarbon-based chain comprising from 1 to 8 carbon atoms, q is 2 or 3, preferably 3, and more preferentially, the compounds of formula (XIV) are trimethylolpropane triacrylate.

COSMETIC ACTIVE AGENTS iv)

According to a particular embodiment, the process of the invention also comprises the application of iv) at least one cosmetic active agent, to said keratin materials.

More particularly, in the treatment process according to the invention, at least one of the compositions “Cl”, “C2”, “C3”, “C4” or “C5” used comprises one or more cosmetic active agents.

In particular, the cosmetic active agent(s) iv) are chosen from: a) dyestuffs (or colouring agents), in particular chosen from pigments, direct dyes and mixtures thereof, b) active agents for caring for keratin materials, preferably the skin, c) UV-screening agents, and d) mixtures thereof. According to a particular embodiment, the at least one cosmetic active agent is chosen from dyestuffs, preferably chosen from pigments, direct dyes and mixtures thereof, more preferentially pigments.

Needless to say, a person skilled in the art will take care to select this or these optional cosmetic active agent(s), and/or the amount thereof, such that the advantageous properties of the corresponding composition according to the invention are not, or are not substantially, adversely affected by the envisaged addition.

DYESTUFFS

According to a particular embodiment, the process of the invention uses one or more dyestuffs.

More particularly, in the process of the invention, at least one of the compositions “Cl”, “C2”, “C3”, “C4” or “C5” used comprises at least one particulate or non-particulate, water- soluble or water-insoluble dyestuff, preferably in a proportion of at least 0.01% by weight relative to the total weight of the composition considered.

For obvious reasons, this amount is liable to vary significantly with regard to the intensity of the desired colour effect and of the colour intensity afforded by the dyestuffs under consideration, and its adjustment clearly falls within the competence of a person skilled in the art.

Preferably, at least one of the compositions “Cl”, “C2”, “C3”, “C4” or “C5” comprises at least one dyestuff chosen from pigments, direct dyes and mixtures thereof, more preferentially pigments.

More preferentially, the pigment(s) of the invention are chosen from carbon black, iron oxides, in particular yellow, red and black iron oxides, and micas coated with iron oxide, triarylmethane pigments, in particular blue and violet triarylmethane pigments, in particular Blue 1 Fake, azo pigments, in particular red azo pigments, more particularly D&C Red 7, an alkali metal salt of lithol red, in particular the calcium salt of lithol red B, and even more preferentially chosen from red iron oxides, yellow iron oxides and azo pigments, in particular red azo pigments, more particularly D&C Red 7.

PIGMENTS For the purposes of the invention, the term “pigment” means any compound that is capable of imparting colour to keratin materials. These compounds have a solubility in water at 25 °C and at atmospheric pressure (760 mmHg) of less than 0.05% by weight, and preferably less than 0.01% by weight.

As pigments that are suitable for use in the invention, mention may notably be made of the organic and/or mineral pigments known in the art, notably those described in Kirk-Othmer’ s Encyclopedia of Chemical Technology and in Ullmann’s Encyclopedia of Industrial Chemistry.

These pigments may be synthetic or natural.

These pigments may be in pigment powder or paste form.

They may be coated or uncoated.

These pigments may be chosen, for example, from mineral pigments, organic pigments, lakes, pigments with special effects such as nacres or glitter flakes, and mixtures thereof. A pigment that is suitable for use in the invention may be chosen from mineral pigments.

The term “mineral pigment” means any pigment that satisfies the definition in Ullmann’s encyclopedia in the chapter on inorganic pigments. Among the mineral pigments that are useful in the present invention, mention may be made of manganese violet, ultramarine blue, chromium hydrate, ferric blue and titanium, zirconium or cerium oxides or dioxides, and also of zinc, iron or chromium oxides.

They may also be pigments having a structure that may be, for example, of sericite/brown iron oxide/titanium dioxide/silica type. Such a pigment is sold, for example, under the reference Coverleaf NS or JS by the company Chemicals and Catalysts, and has a contrast ratio in the region of 30. They may also be pigments having a structure that may be, for example, of silica microsphere type containing iron oxide. An example of a pigment having this structure is the product sold by the company Miyoshi under the reference PC Ball PC- LL-100 P, this pigment being constituted of silica microspheres containing yellow iron oxide.

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

A pigment that is suitable for use in the invention may be chosen from organic pigments.

The term “organic pigment” refers to any pigment that satisfies the definition in Ullmann’s encyclopedia in the chapter on organic pigments. Among the organic pigments that are useful in the present invention, mention may be made of nitroso, nitro, azo, xanthene, pyrene, quinoline, anthraquinone, triphenylmethane, fluorane, phthalocyanine, metal-complex, isoindolinone, isoindoline, quinacridone, perinone, perylene, diketopyrrolopyrrole, indigo, thioindigo, dioxazine, triphenylmethane and quinophthalone compounds. In particular, the white or coloured organic pigments may be chosen from carmine, carbon black, aniline black, azo yellow, quinacridone, phthalocyanine blue, the blue pigments codified in the Color Index under the references CI 42090, 69800, 69825, 74100, 74160, the yellow pigments codified in the Color Index under the references CI 11680, 11710, 19140, 20040, 21100, 21108, 47000, 47005, the green pigments codified in the Color Index under the references CI 61565, 61570, 74260, the orange pigments codified in the Color Index under the references CI 11725, 45370, 71105, the red pigments codified in the Color Index under the references CI 12085, 12120, 12370, 12420, 12490, 14700, 15525, 15580, 15620, 15630, 15800, 15850, 15865, 15880, 26100, 45380, 45410, 58000, 73360, 73915, 75470, the pigments obtained by oxidative polymerization of indole or phenol derivatives as described in patent FR 2 679 771.

Examples that may also be mentioned include pigment pastes of organic pigments, such as the products sold by the company Hoechst under the names: Cosmenyl Yellow IOG: Yellow 3 pigment (CI 11710); Cosmenyl G yellow: Yellow 1 pigment (CI 11680); Cosmenyl GR orange: Orange 43 pigment (CI 71105); Cosmenyl R red: Red 4 pigment (CI 12085); Cosmenyl FB carmine: Red 5 pigment (CI 12490); Cosmenyl RL violet: Violet 23 pigment (CI 51319); Cosmenyl A2R blue: Blue 15.1 pigment (CI 74160); Cosmenyl GG green: Green 7 pigment (CI 74260); Cosmenyl R black: Black 7 pigment (CI 77266).

The pigments in accordance with the invention may also be in the form of composite pigments, as described in patent EP 1 184 426. These composite pigments may notably be composed of particles including a mineral core, at least one binder for attaching the organic pigments to the core, and at least one organic pigment which at least partially covers the core.

The organic pigment may also be a lake.

The term “lake” refers to dyes adsorbed onto insoluble particles, the assembly thus obtained remaining insoluble during use.

The mineral substrates onto which the dyes are adsorbed are, for example, alumina, silica, calcium sodium borosilicate or calcium aluminium borosilicate and aluminium. Among the dyes adsorbed on organic substrates, mention may be made of carminic acid. Mention may also be made of the dyes known under the following names: D & C Red 21 (CI 45 380), D & C Orange 5 (CI 45 370), D & C Red 27 (CI 45 410), D & C Orange 10 (CI 45 425), D & C Red 3 (CI 45 430), D & C Red 4 (CI 15 510), D & C Red 33 (CI 17 200), D & C Yellow 5 (CI 19 140), D & C Yellow 6 (CI 15 985) D & C Green 5 (CI 61 570), D & C Yellow 10 (CI 77 002), 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 (P-carotene, lycopene), xanthophylls (capsanthin, capsorubin, lutein), palm oil, Sudan brown, quinoline yellow, annatto, curcumin, betanin (beet), carmine, copper chlorophyllin, methylene blue, anthocyanins (enocianine, black carrot, hibiscus, elderberry), caramel, riboflavin, beet juice and caramel.

An example of a lake that may be mentioned is the product known under the following name: D&C Red 7 (CI 15 850:1).

The pigment may also be a pigment with special effects.

The term “pigments with special effects” means pigments that generally create a coloured appearance (characterized by a certain shade, a certain vivacity and a certain level of luminance) that is non-uniform and that changes as a function of the conditions of observation (light, temperature, angles of observation, etc.). They thereby differ from coloured pigments, which afford a standard uniform opaque, semi-transparent or transparent shade.

Several types of pigments with special effects exist: those with a low refractive index, such as fluorescent or photochromic pigments, and those with a higher refractive index, such as nacres, interference pigments or glitter flakes.

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

The pigments may be dispersed in the composition by means of a dispersant.

This dispersant may be a surfactant, an oligomer, a polymer or a mixture of several thereof, bearing one or more functionalities with strong affinity for the surface of the particles to be dispersed. In particular, they may become physically or chemically attached to the surface of the pigments. These dispersants also contain at least one functional group that is compatible with or soluble in the continuous medium. In particular, esters of 12- hydroxystearic acid in particular and of Cs to C20 fatty acid and of polyols such as glycerol or diglycerol are used, such as poly(12-hydroxystearic acid) stearate with a molecular weight of approximately 750 g/mol, such as the product sold under the name Solsperse 21 000 by the company Avecia, polyglyceryl-2 dipolyhydroxystearate (CTFA name) sold under the reference Dehymyls PGPH by the company Henkel, or poly hydroxy stearic acid such as the product sold under the reference Arlacel P100 by the company Uniqema, and mixtures thereof. As other dispersants that may be used in the compositions of the invention, mention may be made of quaternary ammonium derivatives of polycondensed fatty acids, for instance Solsperse 17 000 sold by the company Avecia, and polydimethylsiloxane/oxypropylene mixtures such as those sold by the company 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. According to a particular embodiment, the dispersant(s) are of amino silicone type other than the alkoxysilanes described previously and are cationic. Preferably, the pigment(s) are chosen from mineral, mixed mineral-organic, or organic pigments.

According to a particular embodiment, the pigment(s) according to the invention are organic pigments, preferentially organic pigments surface-treated with an organic agent chosen from silicone compounds.

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

DIRECT DYES

According to a particular embodiment of the invention, the cosmetic active agent is a dyestuff chosen from one or more direct dyes.

The term “direct dye” means natural and/or synthetic dyes, other than oxidation dyes. These are dyes that will spread superficially on the fibre. They may be ionic or nonionic, preferably cationic or nonionic.

Among the direct dyes that are suitable for use in 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. The direct dyes are preferably cationic direct dyes. Mention may be made of the hydrazono cationic dyes of formulae (A) and (B) below and the azo cationic dyes of formulae (C) and

(D) below:

Het⁺-C(Ra)=N-N(Rb)-Ar, Q (A)

Het⁺-N(Ra)-N=C(Rb)-Ar, Q (B)

Het⁺-N=N-Ar, Q (C)

Ar⁺-N=N-Ar”, Q“ (D) in which formulae (A) to (D):

- Het⁺ represents a cationic heteroaryl radical, preferentially bearing an endocyclic cationic charge, such as imidazolium, indolium or pyridinium, which is optionally substituted, preferentially with at least one (Ci-Cs)alkyl group such as methyl;

- Ar⁺ represents an aryl radical, such as phenyl or naphthyl, bearing an exocyclic cationic charge, preferentially ammonium, particularly tri(Ci-C8)alkylammonium, such as trimethylammonium;

- Ar represents an aryl group, notably phenyl, which is optionally substituted, preferentially with one or more electron-donating groups such as optionally substituted (Ci-Cs)alkyl, optionally substituted (Ci-Cs)alkoxy, (di)(Ci-C8)(alkyl)amino optionally substituted on the alkyl group(s) with a hydroxyl group, aryl(Ci-C8)alkylamino, and optionally substituted N- (Ci-C8)alkyl-N-aryl(Ci-C8)alkylamino or alternatively Ar represents a julolidine group;

- Ar” represents an optionally substituted (hetero)aryl group, such as phenyl or pyrazolyl, which are optionally substituted, preferentially with one or more (Ci-Cs)alkyl, hydroxyl, (di)(Ci-C8)(alkyl)amino, (Ci-Cs)alkoxy or phenyl groups;

- Ra and Rb, which may be identical or different, represent a hydrogen atom or a (Ci-Cs)alkyl group, which is optionally substituted, preferentially with a hydroxyl group; or else the substituent Ra with a substituent of Het⁺ and/or Rb with a substituent of Ar form, together with the atoms that bear them, a (hetero)cycloalkyl; in particular, Ra and Rb represent a hydrogen atom or a (Ci-C4)alkyl group optionally substituted with a hydroxyl group;

- Q" represents an organic or mineral anionic counterion, such as a halide or an alkyl sulfate. In particular, mention may be made of the azo and hydrazono direct dyes bearing an endocyclic cationic charge of formulae (A) to (D) as defined previously, more particularly the cationic direct dyes bearing an endocyclic cationic charge described in patent applications WO 95/15144, WO 95/01772 and EP 714 954.

Preferably, the direct dyes are chosen from the compounds of formulae (E) and (F) below:

in which formulae (E) and (F):

- R¹ represents a (Ci-C4)alkyl group such as methyl;

- R² and R³, which may be identical or different, represent a hydrogen atom or a (Ci-C4)alkyl group, such as methyl;

- R⁴ represents a hydrogen atom or an electron-donating group such as optionally substituted (Ci-Cs)alkyl, optionally substituted (Ci-Cs)alkoxy, or (di)(Ci-C8)(alkyl)amino optionally substituted on the alkyl group(s) with a hydroxyl group; in particular, R⁴ is a hydrogen atom;

- Z represents a CH group or a nitrogen atom, preferentially CH;

- Q" is an anionic counterion as defined previously, in particular a halide, such as chloride, or an alkyl sulfate, such as methyl sulfate or mesyl.

In particular, the dyes of formulae (E) and (F) are chosen from Basic Red 51, Basic Yellow 87 and Basic Orange 31 or derivatives thereof with Q’ being an anionic counterion as defined previously, particularly a halide such as chloride, or an alkyl sulfate such as methyl sulfate or mesyl. The direct dyes may be chosen from anionic direct dyes. The anionic direct dyes of the invention are dyes commonly referred to as “acid” direct dyes owing to their affinity for alkaline substances. The term “anionic direct dye” means any direct dye including in its structure at least one CO2R’ or SO3R’ substituent with R’ denoting a hydrogen atom or a cation originating from a metal or an amine, or an ammonium ion.

The anionic direct dyes may be chosen from direct nitro acid dyes, azo acid dyes, azine acid dyes, triarylmethane acid dyes, indoamine acid dyes, anthraquinone acid dyes, indigoid dyes and natural acid dyes.

Among the natural direct dyes that may be used according to the invention, mention may be made of lawsone, juglone, alizarin, purpurin, carminic acid, kermesic acid, purpurogallin, protocatechaldehyde, indigo, isatin, curcumin, spinulosin, apigenidin and orceins. Use may also be made of extracts or decoctions containing these natural dyes and notably henna-based poultices or extracts.

Preferably, the direct dyes are chosen from anionic direct dyes.

The dyestuffs, preferably the pigments, may be present in concentrations ranging from 0.01% to 30% by weight, preferably from 0.02% to 20% by weight and more particularly from 0.05% to 15% by weight relative to the total weight of the composition containing them.

The direct dye(s) may be present in concentrations ranging from 0.001% to 10% by weight and preferably from 0.005% to 5% by weight relative to the total weight of the composition containing them.

Preferably, the cosmetic active agent(s), in particular the dyestuff(s) and more particularly the pigment(s), are introduced into at least one of the compositions “Cl”, “C2”, “C3”, “C4” or “C5”.

CARE ACTIVE AGENTS

According to a particular embodiment, the process of the invention uses one or more care active agents.

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 care active agents, preferably in a proportion of at least 0.01% by weight relative to the total weight of the composition considered. In particular, the care active agent may be at least one hydrophilic active agent and/or one lipophilic active agent, and preferably a hydrophilic care active agent. The term “hydrophilic active agent” means a water-soluble or water-dispersible active agent that is capable of forming hydrogen bonds.

The cosmetic care active agent(s) may notably be chosen from: a) vitamins and derivatives thereof, notably esters thereof, in particular tocopherol (vitamin E) and esters thereof (such as tocopheryl acetate), ascorbic acid (vitamin C) and derivatives thereof; b) humectants, in particular urea, hydroxyureas, glycerol, polyglycerols, glycerolglucoside, diglycerolglucoside, polyglycerylglucosides and xylitylglucoside, and in particular glycerol; c) C-glycoside compounds; d) antioxidant compounds; e) anti-ageing active agents, in particular hyaluronic acid compounds, and notably sodium hyaluronate, retinol and derivatives thereof, salicylic acid compounds and in particular n-octanoyl-5-salicylic acid (capryloyl salicylic acid), caffeine, adenosine, c-P-d-xylopyranoside-2-hydroxypropane and the sodium salt of 3-hydroxy-2-pentylcyclopentyl)acetic acid; f) skincare agents chosen from allantoin, panthenol and protein hydrolysates; g) polyphenols, notably escin, ruscus, diosmin, hesperidin and resveratrol, and h) mixtures thereof.

In particular, in the process of the invention, according to one embodiment, at least one of the compositions “Cl”, “C2”, “C3”, “C4” or “C5” used comprises a moisturizer (also known as a humectant agent). Preferably, the care active agent is a moisturizer, and in particular is glycerine (glycerol).

The care active agent(s) may in particular be present, in the composition containing same, 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.

UV-SCREENING AGENTS

According to one embodiment of the process of the invention, at least one of the compositions “Cl”, “C2”, “C3”, “C4” or “C5” used comprises, as cosmetic active agent, at least one UV- screening agent.

The UV-screening agent is a UV-screening agent normally used in cosmetics.

It may be chosen from the positive list contained in Annex VI of (EC) Regulation No. 1223/2009, which specifies the list of UV-screening agents permitted in cosmetics.

The UV-screening agents that are suitable for use in the invention may be of varied nature. They may be lipophilic, hydrophilic or insoluble organic agents. The term “lipophilic UV-screening agent” means any cosmetic or dermatological screening agent that can be fully dissolved in molecular form in a liquid fatty phase or that can be dissolved in colloidal form (for example in micellar form) in a liquid fatty phase.

The term “hydrophilic UV-screening agent” means any cosmetic or dermatological screening agent that can be fully dissolved in molecular form in a liquid aqueous phase or that can be dissolved in colloidal form (for example in micellar form) in a liquid aqueous phase.

The term “insoluble UV-screening agent” means any cosmetic or dermatological screening agent which is not defined either as a lipophilic UV-screening agent or as a hydrophilic UV- screening agent, and which is in the form of particles in aqueous phase or liquid fatty phase. The UV-screening agents of the composition according to the invention may afford UVA and/or UVB photoprotection.

According to a preferred embodiment, the compositions, which are preferably cosmetic compositions, may comprise at least one organic and/or mineral UV-screening agent (for screening out the UV radiation of sunlight).

In particular, the UV-screening agent(s) are chosen from bis-resorcinyl triazine derivatives, dibenzoylmethane derivatives, benzylidenecamphor derivatives, and mixtures thereof. The organic UV-screening agents may also be chosen from anthranilic derivatives; cinnamic derivatives; salicylic derivatives; benzophenone derivatives; phenylbenzotriazole derivatives; benzalmalonate derivatives, notably those mentioned in patent US 5 624 663; phenylbenzimidazole derivatives; imidazolines; 4, 4 -diarylbutadiene derivatives; bis- benzazolyl derivatives, as described in patents EP 6 693 23 and US 2 463 264; p- aminobenzoic acid (PABA) derivatives; methylenebis(hydroxyphenylbenzotriazole) derivatives, as described in patent applications US 5 237 071, US 5 166 355, GB 2 303 549, DE 197 26, 184 and EP 893 119; benzoxazole derivatives, such as those described in patent applications EP 0 832 642, EP 1 027 883, EP 1 300 137 and DE 101 62 844; screening polymers and screening silicones such as those notably described in patent application WO 93/04665; a-alkylstyrene -based dimers such as those described in patent application DE 198 55 649; 4,4-diarylbutadienes such as those described in patent applications EP 0 967 200, DE 197 46 654, DE 197 55 649, EP 1 008 586, EP 1 133 980 and EP 133 981; other merocyanine derivatives such as those described in patent applications WO 04/006878, WO 05/058269 and WO 06/032741, and mixtures thereof. According to a particular embodiment, the concentration of the organic UV- screening agents in the compositions ranges from 1% to 50%, preferably from 1% to 40% by weight, for example from 5% to 35% by weight, relative to the total weight of the composition.

The UV-screening agent(s) may be mineral UV-screening agents, which are generally pigments. The pigments may or may not be coated.

Thus, the mineral UV-screening agents may be chosen from coated or uncoated pigments, and in particular from coated titanium oxide pigments, silicone-treated titanium oxides, 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.

According to a particular embodiment, compositions “Cl” to “C5” are free of mineral UV- screening agents.

According to a particular embodiment, the amount of the mineral UV-screening agent(s) present in compositions “Cl”, “C2”, “C3”, “C4” or “C5” according to the invention may range from 0.01 % to 20% by weight relative to the total weight of the composition containing same. It ranges, for example, from 1% to 15% by weight, relative to the total weight of the composition.

According to a particular embodiment, at least one of the compositions “Cl” to “C5” also comprises one or more organic UV-screening agents and one or more mineral UV-screening agents.

According to a particular embodiment, the compositions comprise a combination of UV- screening agents as described in patent FR 2 977 490, patent application WO 2013/004777 or patent application US 2014/0134120.

Preferably, the process for treating keratin materials, notably keratin fibres, and compositions “Cl”, “C2”, “C3”, “C4” or “C5” use or comprise one or more dyestuffs chosen from pigments, direct dyes and mixtures thereof, preferably pigments; more preferentially, the pigment(s) of the invention are chosen from carbon black, iron oxides, notably yellow, red and black iron oxides, and micas coated with iron oxide, triarylmethane pigments, notably blue and violet triarylmethane pigments, such as Blue 1 Lake, azo pigments, notably red azo pigments, such as D&C Red 7, an alkali metal salt of lithol red, such as the calcium salt of lithol red B, even more preferentially red iron oxides, yellow iron oxides and azo pigments, notably red azo pigments, such as D&C Red 7. FATTY PHASE - FATTY SUBSTANCES

According to a particular embodiment, the process of the invention uses v) one or more fatty substances, in particular one or more oils, preferably volatile oils.

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

In particular, at least one of the compositions “Cl”, “C2”, “C3”, “C4” or “C5” used in the process of the invention comprises one or more fatty substances, in particular one or more oils, preferably volatile oils.

The term “oil” refers to a fatty substance that is liquid at room temperature (20°C) and atmospheric pressure (760 mmHg).

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

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

- hydrocarbon-based oils containing from 8 to 16 carbon atoms, in particular branched Cs-Ci6 alkanes, in particular isoalkanes, more particularly isoalkanes (also known as isoparaffins), preferably C13-C16 isoparaffins, isododecane, isodecane, isohexadecane, for example the oils sold under the trade names Isopar or Permethyl, alone or as mixtures, preferably isododecane (also known as 2,2,4,4,6-pentamethylheptane), linear alkanes, in particular C11-C16 alkanes, alone or as mixtures, in particular hexane, decane, undecane, tridecane, isoparaffins, in particular n-dodecane (C12) and n-tetradecane (C14), the undecanetridecane mixture, mixtures of n-undecane (C11) and n-tridecane (C13), and mixtures thereof and also mixtures of n-undecane (C11) and n-tridecane (C13), and volatile C5-C12 cyclic, nonaromatic alkanes;

- short-chain esters containing from 3 to 8 carbon atoms in total, in particular ethyl acetate, methyl acetate, propyl acetate or n-butyl acetate;

- carbonate hydrocarbon-based oils of structure R’ I-O-C(O)-O-R’2 in which RT and R’2 independently denote a linear, branched or cyclic C4-C8 alkyl group, preferably a C4-C8 alkyl group, advantageously chosen more preferentially from dibutyl carbonate or dipentyl carbonate;

- ether oils of formula R1-O-R2 in which Ri and R2, independently of each other, denote a linear, branched or cyclic C4-C8 alkyl group, preferably a C4-C8 alkyl group;

- silicone oils, in particular comprising from 2 to 7 silicon atoms, and optionally including alkyl or alkoxy groups containing from 1 to 10 carbon atoms, in particular dimethicones of viscosity 5 and 6 cSt, cyclopentadimethylsiloxane, dodecamethylpentasiloxane, cyclohexadimethylsiloxane, octamethylcyclotetrasiloxane, decamethylcyclopentasiloxane, dodecamethylcyclohexasiloxane, heptamethylhexyltrisiloxane, heptamethyloctyltrisiloxane, hexamethyldisiloxane, octamethyltrisiloxane, decamethyltetrasiloxane, dodecamethylpentasiloxane, and mixtures thereof; more preferentially, the volatile oil(s) v) are chosen from Cs-Ci6 alkanes, in particular branched alkanes, preferably isododecane.

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 oils, preferably chosen from:

- non-volatile fluoro oils, in particular chosen from fluorinated polyethers, fluoro silicone oils and fluorosilicones;

- non-volatile silicone oils, in particular chosen from non-volatile silicones having the following INCI names: dimethicone, dimethiconol, trimethyl pentaphenyl trisiloxane, tetramethyl tetraphenyl trisiloxane, diphenyl dimethicone, trimethylsiloxyphenyl dimethicone, phenyl trimethicone, diphenylsiloxy phenyl trimethicone; and also mixtures thereof;

- non-volatile apolar hydrocarbon-based oils, in particular chosen from linear or branched compounds of mineral or synthetic origin: i) liquid paraffin, ii) squalane, isoeicosane, iii) mixtures of linear, saturated hydrocarbons, more particularly C15-C28 hydrocarbons, in particular mixtures whose INCI names are (C15-C 19) Alkane, (C18-C21) Alkane, (C21- C28) Alkane, iv) hydrogenated or non-hydrogenated polybutenes; v) hydrogenated or nonhydrogenated polyisobutenes, preferably hydrogenated, vi) hydrogenated or nonhydrogenated polydecenes, vii) decene/butene copolymers, butene/isobutene copolymers and viii) mixtures thereof;

- non-volatile polar hydrocarbon-based oils, which may be chosen from: i) saturated, unsaturated, linear or branched C10-C26 fatty alcohols, preferably monoalcohols; in particular, the C10-C26 alcohols are fatty alcohols, which are preferably branched when they comprise at least 16 carbon atoms; preferably, the fatty alcohol comprises from 10 to 24 carbon atoms, and more preferentially from 12 to 22 carbon atoms, in particular such as lauryl alcohol, isostearyl alcohol, oleyl alcohol, 2-butyloctanol, 2-undecylpentadecanol, 2- hexyldecyl alcohol, isocetyl alcohol, octyldodecanol and mixtures thereof; ii) triglycerides consisting of fatty acid esters of glycerol, in particular the fatty acids of which may have chain lengths ranging from C4 to C36, and notably from Cis to C36, these oils possibly being linear or branched, and saturated or unsaturated; by way of example, mention may notably be made of heptanoic or octanoic triglycerides, caprylic/capric acid triglycerides, plant oils such as wheatgerm oil, sunflower oil, grapeseed oil, sesame seed oil, com oil, apricot kernel oil, castor oil, shea oil, avocado oil, olive oil, soybean oil, sweet almond oil, palm oil, rapeseed oil, cottonseed oil, hazelnut oil, macadamia oil, jojoba oil, alfalfa oil, poppy oil, pumpkin oil, marrow oil, blackcurrant oil, evening primrose oil, millet oil, barley oil, quinoa oil, rye oil, safflower oil, candlenut oil, passionflower oil, musk rose oil, groundnut oil, coconut oil, argan oil, passionflower oil, kaya oil; the liquid fraction of shea butter, and the liquid fraction of cocoa butter; and also mixtures thereof; iii) linear aliphatic hydrocarbon-based esters of formula R-C(O)-OR’ in which R-C(O)-O- represents the carboxylic acid residue containing from 2 to 40 carbon atoms, and R’ represents a hydrocarbon-based chain containing from 1 to 40 carbon atoms, aliphatic hydrocarbon-based esters of alkylene glycol, in particular ethylene glycol or propylene glycol; the total number of carbon atoms in particular being at least 10; notably chosen 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 of polyalcohols, such as propylene glycol dioctanoate, cetyl octanoate or tridecyl octanoate, 2- ethylhexyl palmitate, alkyl benzoate, polyethylene glycol diheptanoate, propylene glycol bis(2-ethylhexanoate) and mixtures thereof, hexyl laurate, neopentanoic acid esters, such as isodecyl neopentanoate, isotridecyl neopentanoate, isostearyl neopentanoate or 2- octyldodecyl neopentanoate, isononanoic acid esters, in particular isononyl isononanoate, isotridecyl isononanoate or octyl isononanoate, oleyl erucate, isopropyl lauroyl sarcosinate, diisopropyl sebacate, isocetyl stearate, isodecyl neopentanoate, isostearyl behenate or myristyl myristate; iv) hydroxylated esters, in particular polyglyceryl-2 triisostearate; v) aromatic esters, in particular tridecyl trimellitate, C12-C15 alcohol benzoate, the 2- phenylethyl ester of benzoic acid, and butyloctyl salicylate; vi) linear fatty acid esters with a total carbon number ranging from 35 to 70, in particular pentaerythrityl tetrapelargonate; vii) esters of C24-C28 branched fatty acids or fatty alcohols, in particular triisoarachidyl citrate, pentaerythrityl tetraisononanoate, glyceryl triisostearate, glyceryl tris(2- decyltetradecanoate), pentaerythrityl tetraisostearate, polyglyceryl-2 tetraisostearate or pentaerythrityl tetrakis(2-decyltetradecanoate) ; viii) the polyesters obtained by condensation of dimer and/or trimer of unsaturated fatty acid and of diol, in particular those with the INCI name Dilinoleic Acid/Butanediol Copolymer or Dilinoleic Acid/Propanediol Copolymer; the polyesters obtained by condensation of fatty acid dimer and of diol dimer, in particular dimer dilinoleyl dimer dilinoleate; ix) synthetic ethers containing from 10 to 40 carbon atoms, in particular dicaprylyl ether; x) dialkyl carbonates, the two alkyl chains possibly being identical or different, in particular dicaprylyl carbonate; xi) vinylpyrrolidone copolymers, in particular vinylpyrrolidone/ 1 -hexadecene copolymer; and xii) mixtures thereof;

- the non-volatile carbonate oils may be chosen from the carbonates of formula Rs-O- C(O)-O-R9, with Rs and R9, which may be identical or different, representing a linear or branched C4 to C12 and preferentially Cf> to C10 alkyl chain; the carbonate oils may be dicaprylyl carbonate (or dioctyl carbonate), bis(2-ethylhexyl) carbonate, dipropylheptyl carbonate, dibutyl carbonate, dineopentyl carbonate, dipentyl carbonate, dineoheptyl carbonate, diheptyl carbonate, diisononyl carbonate or dinonyl carbonate and preferably dioctyl carbonate;

- oils known as non-volatile ether oils of formula R1-O-R2 in which Ri and R2 independently denote a linear, branched or cyclic C6-C24 alkyl group, preferably a Ce-Cis alkyl group, and preferably Cs-Ci2 alkyl group. It may be preferable for Ri and R2 to be identical. Linear alkyl groups that may be mentioned include a hexyl group, a heptyl group, an octyl group, a nonyl group, a decyl group, an undecyl group, a dodecyl group, a tridecyl group, a tetradecyl group, a pentadecyl group, a hexadecyl group, a heptadecyl group, an octadecyl group, a nonadecyl group, an eicosyl group, a behenyl group, a docosyl group, a tricosyl group and a tetracosyl group. Branched alkyl groups that may be mentioned include a 1,1 -dimethylpropyl group, a 3-methylhexyl group, a 5-methylhexyl group, an ethylhexyl group, a 2-ethylhexyl group, a 5-methyloctyl group, a 1-ethylhexyl group, a 1-butylpentyl group, a 2-butyloctyl group, an isotridecyl group, a 2-pentylnonyl group, a 2-hexyldecyl group, an isostearyl group, a 2 -heptylundecyl group, a 2-octyldodecyl group, a 1,3- dimethylbutyl group, a l-(l-methylethyl)-2-methylpropyl group, a 1,1,3,3-tetramethylbutyl group, a 3,5,5-trimethylhexyl group, a l-(2-methylpropyl)-3-methylbutyl group, a 3,7- dimethyloctyl group and a 2-(l,3,3-trimethylbutyl)-5,7,7-trimethyloctyl group. As cyclic alkyl groups, mention may be made of a cyclohexyl group, a 3 -methylcyclohexyl group and a 3,3,5-trimethylcyclohexyl group, dilauryl ether, diisostearyl ether, dioctyl ether, nonylphenyl ether, dodecyl dimethylbutyl ether, cetyl dimethylbutyl ether and mixtures thereof.

Preferably, the non-volatile oil(s) are chosen from hydrogenated or non-hydrogenated polyisobutenes, preferably hydrogenated, in particular the non-volatile compounds of the Parleam® range; mixtures of C15-C19 alkanes, and from linear aliphatic hydrocarbon-based esters of formula R-C(O)-OR’ in which R-C(0)-0 represents a carboxylic acid residue containing from 2 to 40 carbon atoms, and R’ represents a hydrocarbon-based chain containing from 1 to 40 carbon atoms, as defined previously, in particular isononyl isononanoate.

More preferentially, the process of the invention uses one or more hydrocarbon-based oils containing from 8 to 16 carbon atoms, and notably branched Cs-Ci6 alkanes, in particular isoalkanes, preferably C13-C16 isoparaffins, isododecane, isodecane, isohexadecane, alone or as mixtures, and more preferentially isododecane.

In particular, the amount of oil(s) in at least one of the compositions “Cl”, “C2”, “C3”, “C4” or “C5” used in the process according to the invention ranges from 1% to 50% by weight, relative to the total weight of the composition, more particularly from 2% to 30% by weight, preferentially from 3% to 20%, better still from 5% to 15% by weight, relative to the total weight of the composition. COMPOSITIONS

According to a preferred embodiment, the process for treating keratin materials according to the invention uses water, and the composition(s) “Cl” to “C5” used in the process of the invention comprise water.

Thus, in particular, composition “Cl” is aqueous or aqueous-alcoholic. Preferably, composition “Cl” is aqueous.

In particular, composition “C2” is aqueous or aqueous-alcoholic. Preferably, composition “C2” is aqueous.

In particular, composition “C3” is aqueous or aqueous-alcoholic. Preferably, composition “C3” is aqueous.

In particular, composition “C4” is aqueous or aqueous-alcoholic. Preferably, composition “C4” is aqueous.

In particular, composition “C5” is aqueous or aqueous-alcoholic.

More particularly, the compositions “Cl”, “C2”, “C3”, “C4” and/or “C5”, preferably “Cl”, “C2” and/or “C3”, are aqueous.

According to a particular embodiment, the compositions “Cl”, “C2”, “C3”, “C4” and/or “C5” are aqueous-alcoholic. In particular, they comprise an ethanol/water mixture, in particular in a volume ratio of between 1/99 and 99/1, more particularly between 10/90 and 90/10, even more particularly between 20/80 and 80/20, preferably 40/60 to 60/40, such as 50/50.

According to a particular embodiment, 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 10/90 and 90/10, even more particularly between 20/80 and 80/20, preferably 40/60 to 60/40, such as 50/50.

According to a particular embodiment, the compositions “Cl”, “C2”, “C3”, “C4” or “C5” may be in anhydrous, water-in-oil emulsion or oil-in-water emulsion form.

According to a particular embodiment, composition “Cl” is anhydrous. In particular, composition “Cl” is anhydrous, and it comprises at least one oil, in particular a volatile oil, preferably isododecane.

According to a particular embodiment, composition “C2” is anhydrous. In particular, composition “C2” is anhydrous, and it comprises at least one oil, in particular a volatile oil, preferably isododecane. According to a particular embodiment, composition “C3” is anhydrous. In particular, composition “C3” is anhydrous, and it comprises at least one oil, in particular a volatile oil, preferably isododecane.

According to another particular embodiment of the invention, composition “C4” is anhydrous. According to another variant, composition “C5” is anhydrous.

The compositions “Cl” to “C5” used in the process of the invention may also comprise one or more organic solvents, different from the water-soluble solvent(s) with which the compound(s) of formula (I) may be used.

The term “organic solvent” means an organic substance that is capable of dissolving another substance without chemically modifying it.

Examples of organic solvents that may be mentioned include a) C2-C6 alkanols, such as ethanol and isopropanol; b) polyols that are miscible with water at room temperature (25°C), notably chosen from polyols notably containing from 2 to 10 carbon atoms, preferably containing from 2 to 6 carbon atoms, such as glycerol, propylene glycol, 1,3 -propanediol, butylene glycol, pentylene glycol, hexylene glycol, dipropylene glycol, diethylene glycol or diglycerol; c) polyol ethers, such as 2-butoxyethanol, propylene glycol monomethyl ether, diethylene glycol monoethyl ether or diethylene glycol monomethyl ether; and also d) aromatic alcohols, such as benzyl alcohol or phenoxyethanol, and mixtures thereof.

According to a particular embodiment, the composition also comprises one or more polyols notably chosen from polyols notably containing from 2 to 10 carbon atoms, preferably containing from 2 to 6 carbon atoms, preferably glycerol.

The compositions “Cl”, “C2”, “C3”, “C4” or “C5” used in the process of the invention may also comprise one or more adjuvants commonly used in cosmetics, in particular chosen from thickeners, film-forming agents other than the compounds of formula (I), gelling agents and trace elements, softeners, sequestrants, fragrances, basifying or acidifying agents, dispersants, preserving agents, fillers, surfactants, hair-loss counteractants, anti-dandruff agents, free-radical scavengers, propellants, polar additives and polymers, or mixtures thereof.

Another subject of the invention is a composition “C3”, which is preferably aqueous, comprising i) at least one compound of formula (I) and also the optical and geometrical isomers thereof, the salts thereof with an organic or mineral acid or base, and/or the solvates thereof, such as the hydrates, as defined previously, ii) at least one crosslinking agent, in particular as defined previously, iv) at least one cosmetic active agent, in particular as defined previously, and optionally iii) water.

Another subject of the invention is a composition “C3”, which is preferably aqueous, comprising i) at least one compound of formula (I) and also the optical and geometrical isomers thereof, the salts thereof with an organic or mineral acid or base, and/or the solvates thereof, such as the hydrates, as defined previously, ii) at least one crosslinking agent, in particular as defined previously, iv) at least one cosmetic active agent, in particular as defined previously, and optionally iii) water, the compound(s) of formula (I) and also the optical and geometrical isomers thereof, the organic or mineral acid or base salts thereof, and the solvates thereof, being present in a content of at least 2% by weight, relative to the total weight of the composition.

Another subject of the invention is the cosmetic use of composition “C3”, as defined previously, for treating keratin materials, in particular for caring for, styling and/or colouring keratin fibres, preferably the hair.

A composition “Cl”, “C2”, “C3”, “C4” or “C5” according to the invention is generally suitable for application to keratin materials, in particular application to the skin, lips and/or keratin fibres, and thus generally comprises a physiologically acceptable medium, i.e. a medium that is compatible with keratin materials, in particular application to the skin, lips and/or keratin fibres, notably human keratin fibres such as the hair.

It is preferably a cosmetically acceptable medium, i.e. a medium which has a pleasant colour, odour and feel and which does not cause any unacceptable discomfort, i.e. stinging or tautness, liable to discourage the user from applying this composition.

A composition “Cl”, “C2”, “C3”, “C4” or “C5” may be in the form of a makeup product, in particular a coloured makeup product, for the skin, in particular a foundation, optionally having care properties, a blusher, a face powder, an eyeshadow, a concealer, an eyeliner; a lip makeup product such as a lipstick, optionally having care properties, a lip gloss or lip pencils; a makeup product for the integuments such as the nails or eyelashes, in particular in the form of a cake mascara, or for the eyebrows and the hair, or a product for the temporary tattooing of bodily skin.

According to a particular embodiment, a composition “Cl”, “C2”, “C3”, “C4” or “C5” is in the form of: either a coloured product for the lips; or a skincare product, which may be coloured, in particular a cream or a fluid having moisturizing and/or filling and/or tensor properties; or or a haircare product, in particular a hair dyeing product or a styling product notably free of dyestuff, such as a lacquer, or a “styling” product of the mousse or gel type.

KIT

According to yet another of its aspects, the present invention is also directed towards a multi - compartment kit or device, notably a cosmetic kit or device, comprising:

- at least one compartment containing i) at least one compound of formula (I) and also the optical and geometrical isomers thereof, the organic or mineral acid or base salts thereof, and/or the solvates thereof, such as the hydrates, as defined previously, optionally iii) water, and optionally iv) at least one cosmetic active agent, in particular as defined previously, in particular comprising composition “Cl” as defined previously;

- at least one compartment different from the one which contains i) and containing ii) at least one crosslinking agent, in particular as defined previously, optionally iii) water, and optionally iv) at least one cosmetic active agent, in particular as defined previously, in particular comprising composition “C4” as defined previously; and

- optionally, at least one compartment different from those containing i) and ii), and containing iv) at least one cosmetic active agent, in particular as defined previously, which may be identical to or different from that/those optionally contained in the compartments comprising i) and ii).

The invention is illustrated in greater detail by the examples presented below. Unless otherwise indicated, the amounts indicated are expressed as mass percentages.

Example

METHODS AND MEASUREMENTS

SKIN APPLICATION a) One- step protocol The compounds of formula (I) bearing acetoacetate functions, and optionally the crosslinking agents, are mixed together before application. The system remains fluid long enough to allow application to the substrate.

The compositions are applied to a Bioskin type vitro support from Maprecos (Bioskin plate #10) (elastomeric skin- simulating support) using a film spreader (wet thickness of 100 pm). The deposit is left to dry for 24 hours.

After 24 hours of drying, the deposits are evaluated according to the protocols described hereinbelow. b) Two-step protocol

A first composition, termed the “base coat”, is applied to a Bioskin type vitro support from Maprecos (Bioskin plate #10) (elastomeric skin- simulating support) using a film spreader (wet thickness of 100 pm). The deposit is left to dry for 24 h.

After this first gesture, a second composition, termed the “top coat”, is applied in the same manner.

The deposit is left to dry for 24 hours.

After 24 hours of drying, the deposits are evaluated according to the protocols described hereinbelow.

RESISTANCE TO ADHESIVE TAPE

A piece of adhesive tape (Scotch® Magic™ 810 obtained from 3M ; w = 19 mm, L = 5 cm) is applied to the deposit. A weighted load of about 1070 g is placed on the piece of adhesive tape for 30 seconds. The piece of adhesive tape is then removed and mounted on a slide holder so as to properly observe the result. The adherence of the film to the support is thus evaluated.

RESISTANCE TO OLIVE OIL/SEBUM/WATER

0.5 mL of olive oil, sebum or water is applied to the film of formulation. After 5 minutes, the olive oil, sebum or water is removed by wiping 15 times with cotton wool. The deterioration of the film following contact with the drop of attacking agent is thus examined. In the case of a two-step protocol, for each combination, evaluations are performed on the “base coat” composition alone after drying, and on the system of “base coat” + “top coat” compositions after drying, the objective being to observe the cosmetic properties improved by such combinations.

The resistance is evaluated according to the following scale:

+++: Cosmetic property evaluated as highly effective, no attack of the deposit, which is as it was originally;

++: Cosmetic property evaluated as moderately effective, a little transfer but the deposit is as it was originally;

+: Cosmetic property evaluated as poor, the deposit is slightly altered and some transfer is observed.

0: Cosmetic property evaluated as unsatisfactory, the deposit is completely degraded and there is a lot of transfer to the cotton wool.

EVALUATION OF THE MATTNESS

The formulas are applied using an applicator (wet thickness 100 pm) to a contrast chart (reference: byko-charts Opacity chart #2810).

Using a glossmeter, the gloss is measured at 20° (angle of incidence) from the chart, followed by measuring the gloss/mattness of the deposit 24 hours after application.

GLOSS PERSISTENCE PROTOCOL

The compositions, comprising a compound of formula (I), a mattifying agent (Stearalkonium hectorite, sold under the reference Bentone 27 V CG, by the company Elementis), and/or a crosslinking agent and a solvent, are applied using an applicator (wet thickness of 100 pm) to a contrast chart (reference: byko-charts Opacity chart #2810).

Using a glossmeter, the gloss at 20° (angle of incidence) of the chart is measured, followed by measuring the gloss/mattness of the deposit 24 hours after application.

Once dry, 0.5 mL of water, olive oil and sebum are deposited and left on for 5 minutes.

The drops of attacking agents are then rubbed off using cotton wool (15 strokes) and the gloss/mattness is measured on the attacked area (average of 5 measurements).

HAIR DYEING APPLICATION

The hair dyeing evaluation protocol is detailed below: The evaluations are conducted according to two different protocols: in 1 or 2 step(s), each on locks of natural hair containing 90% white hair strands. a) One- step protocol

The compounds of formula (I) bearing acetoacetate functions, and optionally the crosslinking agents, are mixed together before application. The system remains fluid long enough to allow application to the substrate.

The composition is applied to locks of dry natural hair containing 90% white hairs, at a rate of 1 g of composition per gram of lock.

The locks of hair are left for 5 minutes at room temperature.

The locks of hair are then combed and dried with a hairdryer for 3 minutes.

The locks of hair are left at room temperature for 18 hours at 80% relative humidity. The hair is dyed uniformly and intensely.

The locks of hair thus coloured are then subjected to a test of several repeated shampoo washes so as to evaluate the fastness (persistence) of the colouring obtained with respect to shampoo washing, according to the shampoo washing protocol described below. b) Two-step protocol

A first composition, termed the “base coat”, is applied to locks of dry natural hair containing 90% white hairs, in a proportion of 0.5 g of composition per gram of lock. The locks are then combed. This deposit is applied to the keratin materials, and there is then a waiting period of between 10 seconds and 24 hours, particularly between 1 minute and 1 hour such as 30 minutes, at room temperature (25°C). This drying step may be accelerated by heating the keratin material after application, for example using a hairdryer.

After this first gesture, a second composition, termed the “top coat”, is applied to the lock of hair, at a rate of 0.5 g per gram of lock.

After application, the locks of hair are combed and dried with a hairdryer.

The locks of hair are left at room temperature for 24 hours under a fume cupboard. The hair is dyed uniformly and intensely.

The locks of hair thus coloured are then subjected to a test of several repeated shampoo washes so as to evaluate the fastness (persistence) of the colouring obtained with respect to shampoo washing, according to the shampoo washing protocol described below.

SHAMPOO WASHING PROTOCOL The locks of dyed hair are combed, moistened with water at 35°C and then passed between the fingers five times for 5 seconds. The locks of hair are then squeezed dry between two fingers.

A standard shampoo (Gamier Ultra Doux) is applied uniformly to the dyed locks, in a proportion of 0.4 g of standard shampoo per gram of locks, the locks of hair being massaged gently along the length (6 passes) for 15 seconds, from the root to the end.

The locks of hair are then placed on a watch glass and left to stand for 1 minute.

Next, the locks of hair are rinsed with water while passing the lock between the fingers (15 passes). The locks of hair are then squeezed dry between two fingers before the next shampoo wash.

Once the tests of several shampoo washes have been performed, the locks of hair are combed and dried with a hairdryer.

PERSISTENCE PROTOCOL

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

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

The persistence of the colouring is evaluated by the colour difference AE between the dyed locks before shampooing, then after having undergone 1 and 3 shampoo washes according to the protocol described above. The lower the AE value, the more persistent the colour with respect to shampoo washing.

The AE value is calculated according to the following equation:

[Math 1]

In this equation, L*a*b* represent the values measured after dyeing the hair and after performing the shampoo washes, and Lo*ao*bo* represent the values measured after dyeing the hair but before shampoo washing.

STYLING APPLICATION: STYLING EVALUATION PROTOCOL The styling evaluation protocol is detailed below:

1) Application without crosslinking agent

2 g of a solution containing the formulae described hereinbelow are applied to a lock (90% Natural White NW hair, length 20.5 cm) spread out on aluminium foil, the lock is then wrapped around a brush (approximately 2 cm in diameter and over a length of 3 cm) and held by a hair clip for 24 hours, after which the lock is released from the support (brush + clip).

The length of the lock is measured immediately and 24 hours later, after storage at room temperature at 25 °C.

To check the water persistence after the 24-hour measurements, the locks are immersed in a water bath for 20 minutes, and then dried hanging at room temperature for 24 hours and measured.

A comparison of the curl retention is made between the compositions according to the invention and the comparative compositions.

2) Application with crosslinking agent

2 g of a solution containing the formulae described hereinbelow (“Base coat”) are applied to a lock (90% Natural White NW hair, length 20.5 cm) spread out on aluminium foil, and then, directly afterwards, 2 g of a solution comprising at least one crosslinking agent are applied (“Top Coat”). The lock is wrapped around a brush (approximately 2 cm in diameter and over a length of 3 cm) and held in place by a hair clip for 24 hours, after which the lock is released from the support (brush + clip).

EXAMPLE 1: Synthesis of pullulan bearing an acetoacetate function (polysaccharide 1)

Polysaccharide 1 was prepared according to the following scientific article “Enzyme-

Responsive Biopolymeric Nanogel Fibers by Extrusion: Engineering of High-Surface- Area Hydrogels and Application in Bacterial Enzyme Detection”, ACS Applied Materials and Interfaces, 13(11), pages 12928-12940 (2021).

350 g of DMSO are introduced into a three-necked flask (1 litre) on which is mounted Dean- Stark apparatus and a condenser. The reaction medium is heated to 90°C and stirred using a magnetic bar. 42.5 g of pullulan are then added by successive additions, making sure that each fraction introduced is soluble (added over about 24 h). 23 g of tert-butyl acetoacetate are added dropwise via a dropping funnel, and the mixture is then maintained at 120°C for 2 h. After 2 h, the mixture is returned to 60°C.

The mixture is then introduced dropwise into cold isopropanol (ice bath) - fractional addition in 5 x 600 mL. A paste is obtained and is filtered off on a Buchner funnel, dried (rotavapor 45°C) and then redissolved at 90°C in DMSO. After cooling to room temperature, the mixture is introduced portionwise into cold acetone (4 x 600 mL) in an ice bath.

A white solid is obtained, which is then filtered off on a Buchner funnel.

The product is then dried at 45°C under reduced pressure (rotavapor), then under high vacuum (Schlenk line 50°C, 8 h).

EXAMPLE 2: Synthesis of myristoyl pullulan bearing an acetoacetate function

(polysaccharide 2)

The synthesis is represented by the following preparation scheme:

in which scheme: m is as defined previously;

R¹¹ is as defined previously; - R¹², which may be identical or different, represent a hydrogen atom or an n-Ci3H27-

C(O)- group, it being understood that myristoyl pullulan contains at least one C13H27- C(O)- group.

20 g of myristoyl pullulan and 100 g of tert-butyl acetoacetate are introduced into a threenecked round-bottomed flask (250 mL) equipped with a mechanical stirrer and a distillation column. The reaction medium is heated using an oil bath (oil bath temperature 150°C- 160°C) for 10 hours. The reaction medium is then purified on a rotavapor at 150°C under continuous vacuum, and 100 g of isododecane are then added. The extract is rectified to 25% active agent in isododecane. The polymer is obtained in the form of a solution in isododecane. EXAMPLE 3: Synthesis of raffinose polysaccharide bearing an acetoacetate function

(polysaccharide 3) The synthesis is represented by the following preparation scheme:

in which scheme R¹³, which may be identical or different, represent a hydrogen atom or a group of formula (XII) as defined previously wherein R^a = R^b = H, and R² = CH3, it being understood that raffinose polysaccharide contains at least one such group of formula (XII).

59 g of (D-(+)-Raffinose pentahydrate) (O-a-D-Galactopyranosyl-( l ^6)-a-D- glucopyranosyl P-D-fructofuranoside), 150 mL of DMSO and 173 g of tert-butyl acetoacetate are introduced into a three-necked round-bottomed flask (500 mL) equipped with a mechanical stirrer and a distillation column. The reaction medium is heated using an oil bath (oil bath temperature circa 140°C) for 3 hours. The reaction medium is then extracted with 2 x 200 mL of demineralised water, and the organic phase is purified on a rotavapor at 130°C under continuous vacuum.

EXAMPLE 4: Synthesis of hydroxypropylcellulose (HPC) polysaccharide bearing an acetoacetate function (polysaccharide 4)

in which scheme R¹⁴, which may be identical or different, represent a hydrogen atom or a group of formula (XII) as defined previously wherein R^a = R^b = H, and R² = CH3, it being understood that HPC polysaccharide contains at least one such group of formula (XII). 80 g of hydroxypropylcellulose (reference Sigma Aldrich 191884 (100K)), 200 g of DMSO and 75 g of tert-butyl acetoacetate are introduced into a reactor (500 mL). The reaction medium is heated using an oil bath (oil bath temperature circa 140°C) for 2 hours. The reaction medium is then purified on a rotavapor at 140°C under continuous vacuum. An amber liquid is obtained, which is then purified via precipitation by transferring the product dropwise into a beaker containing 4 litres of water. The precipitated polymer is then solubilised in 200 mL of ethanol. The precipitation step is repeated, and the obtained product is dried in the oven at 60°C under reduced pressure until its mass is constant.

EXAMPLE 5: Preparation of compositions A and B - Without crosslinking agent Composition A comprising a polysaccharide compound of formula (I), and composition B, free of compound of formula (I), are prepared using the contents indicated in the table hereinbelow. The contents are expressed as weight percentages relative to the total weight of the composition.

Table 1

Compositions A and B are prepared by simply mixing the ingredients detailed in Table 1 using a Speed Mixer (mixing equipment which uses centrifugal force) for 2 minutes, at 3500 rpm and at room temperature.

EXAMPLE 6: 1-step application of compositions A and B to the skin (without crosslinking agent)

Simplex formulations were evaluated to show the performance in terms of skin application. Compositions A and B are applied according to the 1-step skin application protocol described previously.

The deposits are then evaluated according to the olive oil and sebum resistance protocols for the formulations on Bioskin.

The evaluation results are summarized in the table below:

Table 2

It is seen that the application of composition A via the process of the invention allows improved sebum and olive oil resistance to be obtained relative to the application of composition B.

Thus, via the application of composition A according to the process of the invention, deposits that are resistant to daily chemical attack (sebum/olive oil) are obtained.

EXAMPLE 7: Preparation of compositions C and D - With crosslinking agent Compositions C and D are prepared using the contents indicated in the table below. The contents are expressed as weight percentages relative to the total weight of the composition under consideration.

Table 3

The “base coat” compositions are prepared by simply mixing the ingredients detailed in Table 3 using a Speed Mixer (mixing equipment which uses centrifugal force) for 2 minutes, at 3500 rpm and at room temperature. The “top coat” compositions are prepared by simply mixing the ingredients detailed in Table 3 using a Speed Mixer (mixing equipment which uses centrifugal force) for 2 minutes, at 3500 rpm and at room temperature.

EXAMPLE 8: Two-step application of compositions C and D to the skin (with crosslinking agent) Compositions C and D are applied according to the two-step skin application protocol described previously.

The deposits are then evaluated according to the water and olive oil resistance protocols.

The evaluation results are summarized in the table below:

Table 4

It is seen that the application of composition C according to the process of the invention allows improved water and olive oil resistance to be obtained relative to the application of composition D. The application of composition C according to the invention results in particular in a water-resistant deposit.

Thus, via the application of composition C according to the process of the invention, deposits that are resistant to daily chemical attack (water/olive oil) are obtained. EXAMPLE 9: Preparation of compositions E and F - With crosslinking agent Compositions E and F are prepared using the contents indicated in the table below. The contents are expressed as weight percentages relative to the total weight of the composition under consideration.

Table 5

The “base coat” compositions are prepared by simply mixing the ingredients detailed in Table 5 using a Speed Mixer (mixing equipment which uses centrifugal force) for 2 minutes, at 3500 rpm and at room temperature.

The “top coat” compositions are prepared by simply mixing the ingredients detailed in Table 5 using a Speed Mixer (mixing equipment which uses centrifugal force) for 2 minutes, at 3500 rpm and at room temperature. EXAMPLE 10: Two-step application of compositions E and F to the skin (with crosslinking agent)

Compositions E and F are applied according to the two-step skin application protocol described previously.

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

The evaluation results are summarized in the table below:

Table 6 It is seen that the application of composition E according to the process of the invention allows improved water, sebum and olive oil resistance to be obtained relative to the application of composition F.

Thus, via the application of composition E according to the process of the invention, deposits that are resistant to daily chemical attack (water/sebum/olive oil) are obtained.

EXAMPLE 11: Preparation of compositions G and H - With crosslinking agent

Compositions G and H are prepared using the contents indicated in the table below. The contents are expressed as weight percentages relative to the total weight of the composition under consideration.

Table 7 The “base coat” compositions are prepared by simply mixing the ingredients detailed in Table 7 using a Speed Mixer (mixing equipment which uses centrifugal force) for 2 minutes, at 3500 rpm and at room temperature.

The “top coat” compositions are prepared by simply mixing the ingredients detailed in Table 7 using a Speed Mixer (mixing equipment which uses centrifugal force) for 2 minutes, at 3500 rpm and at room temperature.

EXAMPLE 12: Two-step application of compositions G and H to the skin (with crosslinking agent)

Compositions G and H are applied according to the two-step skin application protocol described previously.

The evaluation results are summarized in the table below:

Table 8

It is seen that the application of composition G according to the process of the invention allows improved water, sebum and olive oil resistance to be obtained relative to the application of composition H.

Thus, via the application of composition G according to the process of the invention, deposits that are resistant to daily chemical attack (water/sebum/olive oil) are obtained.

EXAMPLE 13: Preparation of compositions I and J - With crosslinking agent Compositions I and J are prepared using the contents indicated in the table below. The contents are expressed as weight percentages relative to the total weight of the composition under consideration.

Table 9

The “base coat” compositions are prepared by simply mixing the ingredients detailed in Table 9 using a Speed Mixer (mixing equipment which uses centrifugal force) for 2 minutes, at 3500 rpm and at room temperature.

The “top coat” compositions are prepared by simply mixing the ingredients detailed in Table 9 using a Speed Mixer (mixing equipment which uses centrifugal force) for 2 minutes, at 3500 rpm and at room temperature. EXAMPLE 14: Two-step application of compositions I and J to the skin - Evaluation of the mattness

Compositions I and J are applied according to the mattness evaluation protocol described previously.

The evaluation results are summarized in the table below:

Table 10

It is seen that the application of composition I according to the process of the invention makes it possible to obtain a crosslinked film that is more matt than the film obtained by application of composition J.

EXAMPLE 15: Preparation of composition K - With crosslinking agent

Composition K is prepared using the contents indicated in the table below. The contents are expressed as weight percentages relative to the total weight of the composition under consideration.

Table 11

The “base coat” composition is prepared by simply mixing the ingredients detailed in Table 11 using a Speed Mixer (mixing equipment which uses centrifugal force) for 2 minutes, at 3500 rpm and at room temperature.

The “top coat” composition is prepared by simply mixing the ingredients detailed in Table 11 using a Speed Mixer (mixing equipment which uses centrifugal force) for 2 minutes, at 3500 rpm and at room temperature. EXAMPLE 16: Two-step application of composition K to the skin - Evaluation of the gloss/mattness persistence

Composition K is applied according to the gloss/mattness persistence protocol described previously.

The evaluation results are summarized in the table below:

It is seen that the application of composition K according to the process of the invention allows a matt crosslinked film to be obtained. It is also seen that the application of composition K according to the process of the invention allows a significant improvement in the persistence of the mattness, after attack with water, olive oil and sebum.

EXAMPLE 17: Preparation of composition L - With crosslinking agent Composition L is prepared using the contents indicated in the table below. The contents are expressed as weight percentages relative to the total weight of the composition under consideration.

Table 13

The “base coat” composition is prepared by simply mixing the ingredients detailed in Table 13 using a Speed Mixer (mixing equipment which uses centrifugal force) for 2 minutes, at 3500 rpm and at room temperature.

The “top coat” composition is prepared by simply mixing the ingredients detailed in Table 13 using a Speed Mixer (mixing equipment which uses centrifugal force) for 2 minutes, at

3500 rpm and at room temperature. EXAMPLE 18: Two-step hair dyeing application of composition L (with crosslinking agent) Composition L is applied according to the two-step hair dyeing application protocol described previously. The evaluation results are summarized in the table below:

Table 14: Colorimetric measurements

The locks of hair dyed according to the invention have after shampoo washes a AE value of less than 1. There is no significant difference of the colour observed even after 3 shampoo washes. It is thus seen that the application of composition L according to the process of the invention allows very good colour persistence to be obtained.

EXAMPLE 19: Preparation of compositions M to P - Without crosslinking agent Compositions M to P are prepared using the contents indicated in the table below. The contents are expressed as weight percentages relative to the total weight of the composition under consideration.

Compositions M to P are prepared by simply mixing the ingredients detailed in Table 15 using a Speed Mixer (mixing equipment which uses centrifugal force) for 2 minutes, at 3500 rpm and at room temperature.

EXAMPLE 20: Crosslinking agent-free hairstyling application of compositions M to P (without crosslinking agent) - Curl evaluation

Compositions M to P are applied according to the crosslinking agent-free hairstyling protocol described previously.

The results of the curl evaluations are summarized in the table below:

Table 16

It is seen that the application of composition O according to the process of the invention allows the water resistance of the non-crosslinked locks to be significantly improved, compared to the application of compositions M, N and P.

EXAMPLE 21: Preparation of compositions Q and R - With crosslinking agent Compositions Q and R are prepared using the contents indicated in the table below. The contents are expressed as weight percentages relative to the total weight of the composition under consideration.

Table 17

The “base coat” compositions are prepared by simply mixing the ingredients detailed in Table 17 using a Speed Mixer (mixing equipment which uses centrifugal force) for 2 minutes, at 3500 rpm and at room temperature.

The “top coat” compositions are prepared by simply mixing the ingredients detailed in Table 17 using a Speed Mixer (mixing equipment which uses centrifugal force) for 2 minutes, at 3500 rpm and at room temperature. EXAMPLE 22: Two-gesture hairstyling application with crosslinking agent of compositions Q and R - Curl evaluation

Compositions Q and R are applied according to the hairstyling protocol with crosslinking agent described previously.

The results of the curl evaluations are summarized in the table below:

Table 18 It is seen that the lock treated with formula R, according to the process of the invention, significantly improves the shape of the curls, which appear sharper and closer together, unlike the lock treated with the comparative formula Q.

In addition, even after 20 minutes in a water bath followed by 24 hours at room temperature, the lock treated with formula R, according to the process of the invention, has much better curl retention than the lock treated with the comparative formula Q.

EXAMPLE 23: Preparation of compositions S and T - With crosslinking agent Compositions S and T are prepared using the contents indicated in the table below. The contents are expressed as weight percentages relative to the total weight of the composition under consideration.

Table 19

Compositions S and T are prepared by simply mixing the ingredients detailed in Table 19 using a Speed Mixer (mixing equipment which uses centrifugal force) for 2 minutes, at 3500 rpm and at room temperature.

EXAMPLE 24: 1-step application of compositions S and T to the skin (with crosslinking agent)

Simplex formulations were evaluated to show the performance in terms of skin application. Compositions S and T are applied according to the 1-step skin application protocol described previously.

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

The evaluation results are summarized in the table below:

Table 20

It is seen that the application of composition S via the process of the invention allows improved scotch tape, sebum, olive oil and water resistance to be obtained relative to the application of composition T.

Thus, via the application of composition S according to the process of the invention, deposits that are resistant to daily chemical attacks (olive oil/sebum/water) and daily mechanical attacks (adhesive tape test) are obtained.

EXAMPLE 25: Preparation of compositions U - With crosslinking agent

Composition U is prepared using the contents indicated in the table below. The contents are expressed as weight percentages relative to the total weight of the composition under consideration.

Table 21

The “base coat” composition is prepared by simply mixing the ingredients detailed in Table 21 using a Speed Mixer (mixing equipment which uses centrifugal force) for 2 minutes, at 3500 rpm and at room temperature.

The “top coat” composition is prepared by simply mixing the ingredients detailed in Table 21 using a Speed Mixer (mixing equipment which uses centrifugal force) for 2 minutes, at 3500 rpm and at room temperature. EXAMPLE 26: Two-step hair dyeing application of composition U (with crosslinking agent)

Composition U is applied according to the two-step hair dyeing application protocol described previously.

The evaluation results are summarized in the table below:

C* corresponds to the chromaticity in the CIE colorimetric system L*, a*, b* and is calculated using the tollowing equation:

. Table 22: Colorimetric measurements

The locks of hair dyed according to the invention have after shampoo washes a low AC* value (less than 1). There is no significant difference of the chromaticity of colour observed even after 3 shampoo washes. It is thus seen that the application of composition U according to the process of the invention allows very good colour persistence to be obtained especially in terms of chromaticity.

EXAMPLE 27: Preparation of compositions V and W - With crosslinking agent Compositions V and W are prepared using the contents indicated in the table below. The contents are expressed as weight percentages relative to the total weight of the composition under consideration.

Table 23 The “base coat” compositions are prepared by simply mixing the ingredients detailed in Table 23 using a Speed Mixer (mixing equipment which uses centrifugal force) for 2 minutes, at 3500 rpm and at room temperature.

The “top coat” compositions are prepared by simply mixing the ingredients detailed in Table 23 using a Speed Mixer (mixing equipment which uses centrifugal force) for 2 minutes, at 3500 rpm and at room temperature.

EXAMPLE 28: Two-step application of compositions V and W to the skin (with crosslinking agent)

Compositions V and W are applied according to the two-step skin application protocol described previously.

The deposits are then evaluated according to the water resistance protocol.

The evaluation results are summarized in the table below:

Table 24

It is seen that the application of composition V according to the process of the invention allows improved water resistance to be obtained relative to the application of composition W. The application of composition V according to the invention results in particular in a water-resistant deposit.

Thus, via the application of composition V according to the process of the invention, deposits that are resistant to daily chemical attack (water) are obtained.

EXAMPLE 29: Preparation of compositions X and Y - With crosslinking agent Compositions X and Y are prepared using the contents indicated in the table below. The contents are expressed as weight percentages relative to the total weight of the composition under consideration.

Table 25

The “base coat” compositions are prepared by simply mixing the ingredients detailed in Table 25 using a Speed Mixer (mixing equipment which uses centrifugal force) for 2 minutes, at 3500 rpm and at room temperature. The “top coat” compositions are prepared by simply mixing the ingredients detailed in Table 25 using a Speed Mixer (mixing equipment which uses centrifugal force) for 2 minutes, at 3500 rpm and at room temperature.

EXAMPLE 30: Two-step application of compositions X and Y to the skin (with crosslinking agent) Compositions X and Y are applied according to the two-step skin application protocol described previously.

The deposits are then evaluated according to the water resistance protocol for the formulations on Bioskin. The evaluation results are summarized in the table below:

Table 26

It is seen that the application of composition X according to the process of the invention allows improved water resistance to be obtained relative to the application of composition Y. The application of composition X according to the invention results in particular in a water-resistant deposit.

Thus, via the application of composition X according to the process of the invention, deposits that are resistant to daily chemical attack (water) are obtained.

Claims

1. Process for treating keratin materials, comprising the application to said keratin materials, in one or more successive steps, of at least: i) one or more compounds of formula (I) and also the optical or geometrical isomers thereof, the acid or base salts thereof and/or solvates thereof, such as hydrates, or a composition containing same:

(I) in which formula (I):

- R³, which may be identical or different, represents a group chosen from:

1) sulfonate -SO3’, Cat⁺,

2) linear or branched (Ci-C22)alkyl, and

- R^a and R^b, which may be identical or different, represent a hydrogen atom or a (Ci- C4)alkyl group, preferably a hydrogen atom;

- p denotes an integer ranging from 0 to 3;

- An’ represents an anionic counterion;

- Cat’ represents a cationic counterion; ii) optionally at least one crosslinking agent; and iii) optionally water, preferably water, or optionally water mixed with a polar organic solvent, preferably chosen from (C₂-C6)alkanols, more preferentially ethanol.

2. Treatment process according to the preceding claim, in which the compound(s) of formula (I) are such that the polysaccharide radical represented by R¹ is chosen from polysaccharide radicals derived from agarose, starch and derivatives thereof, cationic starch, alginate and derivatives thereof, hyaluronic acid, cellulose and derivatives thereof, in particular chosen from methylcellulose ethylcellulose, hydroxymethylcellulose, hydroxypropylcellulose, hydroxypropylmethylcellulose and hydroxybutylcellulose, carrageenan, curdlan, dextran, glucan, guar gum, gellan, konjac, inulin, pectin, pullulan and scleroglucan, xanthan, raffinose, and derivatives thereof, preferably chosen from starch and derivatives thereof, cellulose and derivatives thereof, alginate and derivatives thereof, and raffinose and derivatives thereof, and more preferentially chosen from hydroxypropylcellulose, pullulan and derivatives thereof, such as myristoyl pullulan, and raffinose.

3. Treatment process according to either of the preceding claims, in which the compound(s) of formula (I) are chosen from: a) cellulose, starch, amylose and derivatives thereof such as hydroxypropylcellulose, of formula (II) and also the optical isomers thereof, the organic or mineral acid or base salts thereof, and the solvates thereof, such as hydrates:

b) alginate, pectin and derivatives thereof of formula (III) and also the optical isomers thereof, the organic or mineral acid or base salts thereof, and the solvates thereof, such as hydrates:

(III) c) hyaluronic acid and derivatives thereof, of formula (IV) and also the isomers and solvates thereof:

g) glucan and derivatives thereof of formula (VIII) and also the optical isomers thereof, the organic or mineral acid or base salts thereof, and the solvates thereof, such as hydrates:

(VIII) h) carrageenan and derivatives thereof of formula (IX) and also the optical isomers thereof, the organic or mineral acid or base salts thereof, and the solvates thereof, such as hydrates:

(IX) in particular chosen from the derivatives y-carrageenan, 6- carrageenan, p-carrageenan, v- carrageenan, X-carrageenan, and the respective basic forms thereof P- carrageenan, a- carrageenan, K-carrageenan, r-carrageenan, 9-carrageenan, it being understood that the carrageenans comprise at least one group of formula (XII), preferably at least two groups of formula (XII); i) cyclodextrin and derivatives thereof, of formula (X):

(XI) k) raffinose and derivatives thereof of formula (XVI):

in which formulae (II) to (XI) and (XVI):

- R⁶, which may be identical or different, represents -CH2-OR⁷ or -C(O)-OR⁷,

- R⁷, which may be identical or different, represent a hydrogen atom or a group R³ as defined in formula (I), preferably a (Ci-C22)alkyl group, optionally substituted with at least one hydroxyl group (-OH) or a group -C(O)-R⁸, with R⁸ representing a (Ci-C22)alkyl group, or a group -CH2-CH(OH)-CH2-N⁺(CH3)3 An’, or a group R⁹ of formula (XII), R⁷ represents a radical R⁷ or a group -SO3’, Cat ⁺, Cat⁺ being as defined previously, or a group of formula

in which formula (XII) R^a, R^b and R² are as defined previously for the compounds of formula (I), preferably R² denotes a methyl radical and R^a and R^b denote a hydrogen atom;

- R¹⁰, which may be identical or different, represent a hydrogen atom, a (Ci-C4)alkyl group, such as -CH3, or a group R⁹ as defined above;

- m denotes an integer ranging from 2 to 3000, in particular from 5 to 2500, more particularly from 10 to 2300, preferably from 15 to 1000, preferentially from 20 to 500, and more preferentially from 25 to 200;

- An’ being as defined previously; it being understood that formulae (II) to (XI) and (XVI) contain at least one unit R⁹, and preferably at least two units R⁹, in their structure. 4. Treatment process according to any one of the preceding claims, in which the compound(s) of formula (I) are chosen from:

- alginic acid 3-oxobutanoate (CAS No.: 2135428-65-6];

- amylose 3-oxobutanoate (CAS No.: 106254-13-1];

- cellulose, 3-oxobutanoate, 2-hydroxyethyl ether (CAS No.: 104708-71-6];

- cellulose, 3-oxobutanoate, carboxymethyl ether (CAS No.: 105953-68-2];

- cellulose, 3-oxobutanoate, 2-hydroxypropyl ether (CAS No.: 105953-69-3];

- cellulose, 3-oxobutanoate, methyl ether (CAS No.: 105953-70-6];

- cellulose, tris(3-oxobutanoate) (CAS No.: 119466-02-3];

- cellulose, 3-oxobutanoate (CAS No.: 80619-14-3];

- cellulose, acetate 3-oxobutanoate (CAS No.: 168608-38-6];

- cellulose, hexanoate 3-oxobutanoate (CAS No.: 1696417-96-5];

- cellulose, 3-oxobutanoate propanoate (CAS No.: 163381-45-1];

- cellulose, butanoate 3-oxobutanoate (CAS No.: 163438-87-7];

- cellulose,

4-methoxy-3-oxobutanoate (CAS No.: 2410687-10-2];

- cellulose, acetate butanoate 3-ethoxypropanoate 3-oxobutanoate (CAS No.: 334475-56- 8];

- cellulose, 2-hydroxypropyl ether, 3-oxobutanoate (CAS No.: 497932-47-5];

- cellulose, 3-oxobutanoate, ethyl ether (CAS No.: 497932-48-6];

- dextran, 3-oxobutanoate (CAS No.: 882428-66-2];

- D-glucan, 3-oxobutanoate (CAS No.: 2135428-66-7];

- guar gum, 3-oxobutanoate (CAS No.: 497932-49-7];

- hyaluronic acid, 3-oxobutanoate (CAS No.: 2135428-62-3];

- starch, 3-oxobutanoate (CAS No.: 78207-15-5];

- starch, 3-oxobutanoate, methyl ether (CAS No.: 2135428-59-8];

- starch, 3-oxobutanoate, 2-carboxymethyl ether (CAS No.: 2135428-60-1];

- starch, 2-hydroxypropyl ether, 3-oxobutanoate (CAS No.: 2135428-61-2];

- starch, 3-oxobutanoate, 2-hydroxypropyl ether (CAS No.: 2223678-15-5];

- pullulan acetoacetate (CAS No.: 2762209-81-2];

- cyclodextrin, ethyl-3-oxobutanoate (CAS No.: 152154-93-3];

- cyclodextrin, 3-oxobutanoate (CAS No.: 2135428-63-4); and - myristoyl pullulan acetoacetate;

- raffinose acetoacetate; and

- hydroxypropylcellulose acetoacetate.

5. Treatment process according to any one of the preceding claims, in which the compound(s) of formula (I) are chosen from raffinose acetoacetate, hydroxypropylcellulose acetoacetate, pullulan acetoacetate and myristoyl pullulan acetoacetate.

6. Treatment process according to any one of the preceding claims, comprising the application to said keratin materials of at least iii) water.

7. Treatment process according to any one of the preceding claims, comprising the application to said keratin materials of at least ii) a crosslinking agent.

8. Treatment process according to any one of the preceding claims, comprising the application to said keratin materials of at least ii) a crosslinking agent chosen from (poly)amine, (poly)thiol, (poly)carbonyl, (poly)acrylate and metal alkoxide compounds and mixtures thereof, preferably chosen from (poly)amine, (poly)thiol, (poly)acrylate compounds and mixtures thereof, and more preferentially chosen from (poly)amine, (poly)thiol compounds and mixtures thereof.

9. Treatment process according to any one of the preceding claims, comprising the application to said keratin materials of at least ii) a crosslinking agent chosen from:

A) (poly)amine compounds chosen from: ia) chitosans such as poly(D-glucosamine), ib) polyether diamines, in particular polyethylene glycol a,co-diamines, bearing a chainend amine function, ic) polyether triamines, in particular poly etheramines (or Jeff amine), id) aminoalkoxy silanes, in particular APTES, ie) spermidine, and if) polydialkylsiloxanes comprising primary amine groups at the end of the chain or on side chains, in particular polydimethylsiloxanes comprising primary amine groups, more particularly bis(3-aminopropyl)-terminated poly(dimethoxysiloxane) (PDMS-diNPE) and amodimethicones comprising amine groups on side chains, more particularly bis-cetearyl amodimethicone;

B) (poly)thiol compounds chosen from: iia) polydialkylsiloxanes bearing thiol functions, and iib) alkoxysilanes bearing thiol functions, and in particular chosen from iia) polydialkylsiloxanes bearing thiol functions, preferably from polydimethylsiloxanes comprising thiol groups on the side chain, in particular mercaptopropyl, and more particularly chosen from the compounds of formula (XIII): R^a-Si(R^b)(R^d)-O-[Si(R^a)(R^b)-O]m-[Si(R^b)(ALKi-SH)-O]n-Si(R^b)(R^d)-R^a (XIII) in which formula (XIII):

R^a and R^b, which may be identical or different, preferably identical, represent a (Ci- C4)alkyl group, 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, preferably a (Ci-C4)alkyl group, more preferentially methyl,

R^d represents a (Ci-C4)alkyl group, 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, an aryl(Ci-C4)alkoxy group, in particular benzoxy, or a (Ci-C6)alkyl group substituted with a (Ci-C4)alkylamino, amino or thiol group, and preferably a (Ci-C4)alkyl group, more preferentially methyl, and preferably R^a, R^b and R^d are identical and represent a (Ci-C6)alkyl group, more preferentially methyl,

ALKi represents a linear or branched, optionally cyclic, saturated or unsaturated divalent hydrocarbon-based chain comprising from 1 to 100 carbon atoms, optionally interrupted with 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 combinations thereof, in particular -O-, -O-C(O)- or -C(O)-O-; preferably, ALKi represents a (Ci-Ce) alkylene and more preferentially (C1-C4) alkylene group, even more preferentially propylene, n and m, which may be identical or different, represent an integer greater than 2, and in particular the values of m and n are such that the weight-average molecular weight of said polyorganosiloxane is between 1000 and 55 000 g.mol ¹; and

C) the (poly)acrylate compounds of formula (XIV): L[-Y-C(O)-C(R^e)=CH₂]_q (XIV) in which formula (XIV): q represents an integer greater than or equal to 2, in particular n is between 2 and 10 and preferably between 2 and 5 inclusive,

L denotes a linear or branched, saturated or unsaturated, or (hetero)cyclic, saturated or unsaturated, 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; L being optionally interrupted and/or terminated with one or more heteroatoms or groups chosen from O, S, N, Si, C(X), and combinations thereof, in particular -O-, -O-C(X)-, -N(R)-C(X)-, -Si(R_c)(Rd)-O- with R representing a hydrogen atom or a (C i-CeJalkyl group, in particular methyl; and/or L being optionally substituted with one or more groups chosen from: -N(R_a)Rb and -(X’)_a-C(X)- (X”)b-R_a; with X, X’ and X”, which may be identical or different, representing an oxygen or sulfur atom, or a group N(Rb); a and b being 0 or 1, preferably the sum of a + b being 1; R_a and Rb, which may be identical or different, represent a hydrogen atom, a (Ci-Ce/alkyl group or an aryl(Ci-C4)alkyl group, in particular benzyl, preferably R_a and Rb represent a hydrogen atom, and R_c and Rd, which may be identical or different, represent a (Ci- Ce/alkyl, aryl(Ci-C4)alkyl or (Ci-Ce/alkoxy group,

R^e represents a hydrogen atom or a (Ci-C4)alkyl group, in particular methyl; preferably, R^e represents a hydrogen atom, and

Y represents an oxygen atom or an amino group -N(H)-, preferably an oxygen atom, preferably Y is an oxygen atom and R^e is a hydrogen atom, preferably L represents a di- or trivalent, preferably trivalent, hydrocarbon-based chain comprising from 1 to 8 carbon atoms, q is 2 or 3, preferably 3, and more preferentially, the compounds of formula (XIV) are trimethylolpropane triacrylate.

10. Treatment process according to any one of the preceding claims, in which iv) at least one cosmetic active agent is also applied to said keratin materials.

11. Treatment process according to the preceding claim, in which the cosmetic active agent(s) iv) are chosen from: a) dyestuffs, in particular chosen from pigments, direct dyes and mixtures thereof, b) active agents for caring for keratin materials, preferably the skin, c) UV-screening agents, and d) mixtures thereof; preferably, the cosmetic active agent(s) iv) are chosen from a) dyestuffs, preferably chosen from pigments, direct dyes and mixtures thereof; more preferentially, the pigment(s) are chosen from carbon black, iron oxides, in particular yellow, red and black iron oxides, and micas coated with iron oxide, triarylmethane pigments, in particular blue and violet triarylmethane pigments, in particular Blue 1 Lake, azo pigments, in particular red azo pigments, more particularly D&C Red 7, an alkali metal salt of lithol red, in particular the calcium salt of lithol red B, and even more preferentially from red iron oxides, yellow iron oxides and azo pigments, in particular red azo pigments, more particularly D&C Red 7.

12. Treatment process according to any one of the preceding claims, in which use is also made of v) at least one fatty substance, in particular at least one oil, preferably at least one volatile oil.

13. Treatment process according to the preceding claim, in which use is also made of v) at least one fatty substance chosen from volatile oils chosen from:

- hydrocarbon-based oils containing from 8 to 16 carbon atoms, in particular branched Cs- Ci6 alkanes, in particular isoalkanes, more particularly isoalkanes (also known as isoparaffins), preferably C13-C16 isoparaffins, isododecane, isodecane, isohexadecane, for example the oils sold under the trade names Isopar or Permethyl, alone or as mixtures, preferably isododecane (also known as 2,2,4,4,6-pentamethylheptane), linear alkanes, in particular C11-C16 alkanes, alone or as mixtures, in particular hexane, decane, undecane, tridecane, isoparaffins, in particular n-dodecane (C12) and n-tetradecane (C14), the undecane-tridecane mixture, mixtures of n-undecane (C11) and n-tridecane (C13), and mixtures thereof and also mixtures of n-undecane (C11) and n-tridecane (C13), and volatile C5-C12 cyclic, non-aromatic alkanes; short-chain esters containing from 3 to 8 carbon atoms in total, in particular ethyl acetate, methyl acetate, propyl acetate or n-butyl acetate; carbonate hydrocarbon-based oils of structure R’ I-0-C(0)-0-R’2 in which R’ 1 and R’2 independently denote a linear, branched or cyclic C4-C8 alkyl group, preferably a C4-C8 alkyl group, advantageously chosen more preferentially from dibutyl carbonate or dipentyl carbonate; ether oils of formula R1-O-R2 in which Ri and R2, independently of each other, denote a linear, branched or cyclic C4-C8 alkyl group, preferably a C4-C8 alkyl group; silicone oils, in particular comprising from 2 to 7 silicon atoms, and optionally including alkyl or alkoxy groups containing from 1 to 10 carbon atoms, in particular dimethicones of viscosity 5 and 6 cSt, cyclopentadimethylsiloxane, dodecamethylpentasiloxane, cyclohexadimethylsiloxane, octamethylcyclotetrasiloxane, decamethylcyclopentasiloxane, dodecamethylcyclohexasiloxane, heptamethylhexyltrisiloxane, heptamethyloctyltrisiloxane, hexamethyldisiloxane, octamethyltrisiloxane, decamethyltetrasiloxane, dodecamethylpentasiloxane, and mixtures thereof; more preferentially, the volatile oil(s) v) are chosen from Cs-Ci6 alkanes, in particular branched alkanes, preferably isododecane.

14. Process for treating, notably for cosmetically treating, keratin materials, according to any one of the preceding claims, in particular for caring for and/or making up the skin, the lips, the eyelashes and/or the eyebrows and/or for caring for, styling and/or colouring keratin fibres, preferably the hair, comprising the application to said keratin materials of at least: a composition, termed “Cl”, comprising i) at least one compound of formula (I) and also the optical and geometrical isomers thereof, the organic or mineral acid or base salts thereof, and/or the solvates thereof, such as the hydrates, according to any one of Claims 1 to 5, optionally iii) water, and optionally iv) at least one cosmetic active agent, in particular according to either of Claims 10 and 11; a composition, termed “C2”, comprising i) at least one compound of formula (I) and also the optical and geometrical isomers thereof, the salts thereof with an organic or mineral acid or base, and/or the solvates thereof, such as the hydrates, according to any one of Claims 1 to 5, optionally ii) at least one crosslinking agent, in particular according to either of Claims 8 and 9, optionally iii) water, and optionally iv) at least one cosmetic active agent, in particular according to either of Claims 10 and 11; a composition, termed “C3”, comprising i) at least one compound of formula (I) and also the optical and geometrical isomers thereof, the salts thereof with an organic or mineral acid or base, and/or the solvates thereof, such as the hydrates, according to any one of Claims 1 to 5, ii) at least one crosslinking agent, in particular according to either of Claims 8 and 9, iv) at least one cosmetic active agent, in particular according to either of Claims 10 and 11, and optionally iii) water; a composition, termed “C4”, comprising ii) at least one crosslinking agent, in particular according to either of Claims 8 and 9, optionally iv) at least one cosmetic active agent, in particular according to either of Claims 10 and 11, and optionally iii) water; and/or a composition, termed “C5”, comprising iv) at least one cosmetic active agent, in particular according to either of Claims 10 and 11, and optionally iii) water; it being understood that compositions “Cl”, “C2”, “C3”, “C4” and “C5” may be anhydrous, aqueous, and/or comprise one or more fatty substances v), in particular according to either of Claims 12 and 13.

15. Treatment process according to the preceding claim, characterized in that it comprises a single step of applying composition “Cl” or composition “C2” or composition “C3” to said keratin materials.

16. Treatment process according to Claim 14, characterized in that it comprises two successive steps of application, to said keratin materials, of two different compositions, preferably of composition “Cl” and then of composition “C4”.

17. Cosmetic treatment process according to Claim 16, for caring for, styling and/or colouring keratin fibres, preferably the hair, comprising the successive application of at least: a composition, termed “Cl”, comprising i) at least one compound of formula (I) and also the optical and geometrical isomers thereof, the organic or mineral acid or base salts thereof, and/or the solvates thereof, such as the hydrates, as defined according to any one of Claims 1 to 5, optionally iii) water, and optionally iv) at least one cosmetic active agent, in particular according to either of Claims 10 and 11; and then a composition, termed “C4”, comprising ii) at least one crosslinking agent, in particular according to either of Claims 8 and 9, optionally iv) at least one cosmetic active agent, in particular according to either of Claims 10 and 11, and optionally iii) water; at least one of the compositions “Cl” and/or “C4” containing at least one dyestuff, in particular according to Claim 11, preferably at least one pigment, and more preferentially composition “Cl” comprises at least one pigment.

18. Composition “C3”, which is preferably aqueous, comprising i) at least one compound of formula (I) and also the optical and geometrical isomers thereof, the salts thereof with an organic or mineral acid or base, and/or the solvates thereof, such as the hydrates, according to any one of Claims 1 to 5, ii) at least one crosslinking agent, in particular according to either of Claims 8 and 9, iv) at least one cosmetic active agent, in particular according to either of Claims 10 and 11, and optionally iii) water.

19. Cosmetic use of composition “C3” according to Claim 18, for treating keratin materials, in particular for caring for, styling and/or colouring keratin fibres, preferably the hair.

20. Multi-compartment kit, notably a cosmetic kit, comprising: at least one compartment containing i) at least one compound of formula (I) and also the optical and geometrical isomers thereof, the organic or mineral acid or base salts thereof, and/or the solvates thereof, such as the hydrates, according to any one of Claims 1 to 5, optionally iii) water, and optionally iv) at least one cosmetic active agent, in particular according to either of Claims 10 and 11, in particular comprising composition “Cl” according to either of Claims 14 and 17; at least one compartment different from the one which contains i) and containing ii) at least one crosslinking agent, in particular according to either of Claims 8 and 9, optionally iii) water, and optionally iv) at least one cosmetic active agent, in particular according to either of Claims 10 and 11, in particular comprising composition “C4” according to either of Claims 14 and 17; and optionally, at least one compartment different from those containing i) and ii), and containing iv) at least one cosmetic active agent, in particular according to either of Claims 10 and 11, which is identical to or different from that/those optionally contained in the compartments comprising i) and ii).

21. Myristoyl pullulan acetoacetate compound, the optical and geometrical isomers thereof, the salts thereof with an organic or mineral acid or base, and/or the solvates thereof, such as hydrates, of formula:

in which formula: m is as defined according to Claim 3;

R¹¹, which may be identical or different, represents a hydrogen atom or a linear or branched, preferably linear, (Cio-Ci6)alkyl group, such as C13H27, or a linear or branched, preferably linear, (Cio-Ci6)alkylcarbonyl group, such as Ci3H27-C(O)-, or a group R⁹ as defined previously; it being understood that at least one, preferably at least two, group(s) R¹¹, and at least one (Cio-Ci6)alkyl or (Cio-Ci6)alkylcarbonyl group, such as C13H27 or Ci3H27-C(O)-, are present in the above compound myristoyl pullulan acetoacetate.

22. Cosmetic composition comprising at least one myristoyl pullulan acetoacetate compound as defined according to Claim 21.