FR3163272A1 - A process for treating keratinous materials and fibers using at least one triglyceride oil with ionic and acetoacetate functions. - Google Patents

Abstract

Method for treating keratinous materials and fibers using at least one triglyceride oil with ionic and acetoacetate functions The present invention relates to a method for treating keratinous materials, particularly for cosmetic purposes, specifically for the care and/or makeup of skin, lips, eyelashes and/or eyebrows, and/or for the care, styling and/or coloring of keratinous fibers, preferably hair, comprising the application to said keratinous materials, in one or more successive steps, of at least i) one or more compounds of formula (I), as well as their optical, geometric and/or solvate isomers, such as hydrates, or a composition containing them, and ii) at least one crosslinking agent.

Description

A process for treating keratinous materials and fibers using at least one triglyceride oil with ionic and acetoacetate functions.

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

Its aim is to propose, in particular, new treatment processes, especially cosmetic ones, including the application to keratinous materials of at least one triglyceride oil functionalized by ionic functions and acetoacetate functions, and at least one crosslinking agent, which are particularly interesting in view of their technical performance, especially in terms of the durability of the deposits they allow to be obtained, and the sensory sensations they provide to the user.

Cosmetic products typically require the use of one or more film-forming polymers to achieve a quality deposit of these products on keratinous materials and keratinous fibers, and in particular to meet the expectations detailed below.

Thus, in the field of skincare, lip, and hair care, it is particularly important that the product does not transfer upon contact with fingers or clothing and that it adheres well to water, especially rain or showering, as well as perspiration and sebum, and even to food oils, particularly cooking oils when applied to the lips. Furthermore, this product must be comfortable, aesthetically pleasing, transparent if uncolored, and ideally glossy. For hair applications, it must also allow for hair movement without altering its appearance, meaning without cracking or flaking. Products that withstand multiple shampoos are also desirable.

To do this, it is used in makeup products, such as mascaras, eyeliners, eyeshadows or lipsticks, and in hair application products, and more particularly in their organic and especially oily phases, as dispersions of nano-sized polymer particles, as a film-forming agent.

However, the compositions of earlier art show an unsatisfactory durability over time.

Film-forming compositions, particularly cosmetic ones, are known to exist that comprise at least one oil phase and at least one copolymer obtained by the polymerization of ethylenic monomers, some of which carry specific groups (see, for example, WO 2022/136104). However, such compositions require the presence of an oil phase, which can limit their range of applications. Furthermore, these compositions do not necessarily meet the demand for naturalness expressed by some consumers.

It is also known from patent EP 1,392,222 to use a cosmetic composition for the care and/or treatment of keratinous materials comprising a supramolecular polymer having a polymeric backbone and at least two groups capable of forming at least three hydrogen bonds, and from patent EP 1,435,900 to use a hair composition comprising a supramolecular polymer having a polymeric backbone and at least two groups capable of forming at least three hydrogen bonds and a surfactant or a hair conditioning agent. However, with these two compositional alternatives, the resulting performance in terms of hold over time or water resistance remains insufficient.

It is also known from WO 2014/099108 of compositions and processes for forming deposits on keratin substrates with good durability, employing compounds with acetoacetate functions and actives functionalized to be covalently linked to keratin materials.

Furthermore, document WO 06/042169 describes fabric adhesives, in medical and veterinary applications, formed by the reaction of poly(hydroxyl) compounds derived with acetoacetate groups and/or polyamino compounds derived with acetoacetamide groups with an aminofunctional crosslinking compound.

It is also known that triglyceride oils with ionic functions are used in cosmetic products. These oils are generally used as emulsifying agents, surfactants, or dispersing agents for pigments. The uses of these oils are described, for example, in documents DE 102017223103 and EP 0283994.

However, these triglyceride oils with ionic functions do not allow for the formation of persistent deposits that are resistant to chemical aggressors such as water and fats, like sebum.

In general, the processes and treatments described above do not allow access to deposits on keratinous materials, particularly on the skin and/or lips, and/or on keratinous fibers, which meet all the aforementioned requirements, namely, very good resistance to water, particularly to shampoos for hair, and/or to oils, especially for lips, which are also comfortable for users to wear, which allow the shine of the deposits to be modulated or which do not lead to visually unsightly, transparent and/or invisible deposits if not colored, which respect the movement of the hair without cracking or flaking, and which, in the case of hair use, provide very satisfactory hold of the style or color retention.

Furthermore, there is significant consumer demand for the use of compositions with a reduced environmental impact.

There therefore remains a need for a treatment process, particularly cosmetic, intended for application on keratinous materials and/or keratinous fibers which allows obtaining a film-forming deposit, non-sticky, which transfers little or not at all, shiny, comfortable, and long-lasting, which is resistant to water and grease, in particular sebum, as well as food fats.

There also remains a need for treatment processes, particularly cosmetic ones, that provide deposits with qualities of shine and/or invisibility.

In particular, there remains a need for a process for treating keratin fibers, especially cosmetic, coloring and intended for hair application, which provides deposits with good resistance to water and shampoos to guarantee color retention over time comparable to direct coloring.

There is also a need for a process for treating keratin fibers, particularly cosmetic, especially non-coloring, intended for hair application which provides styling properties, particularly curl hold, resistant to water.

The present invention is specifically designed to meet all or part of these needs.

These problems are solved by implementing a treatment process, particularly cosmetic, for keratinous materials, especially for the care and/or makeup of the skin, lips, eyelashes and/or eyebrows and/or for the care, styling and/or coloring of keratinous fibers, preferably hair, comprising the application to said keratinous materials, in one or more successive steps, of at least:
(i) one or more compounds of formula (I), as well as its optical, geometric and/or solvate isomers, such as hydrates, or a composition containing it or them:

in which:
- AK1, AK2 and AK3 independently designate a monovalent hydrocarbon chain, linear or branched, saturated or unsaturated, in _C4 - _C30 , in particular in _C6 - _C24 , preferably in _C10 - _C24 , said chain being substituted by one or more ionic groups selected from -O- _PO3H2 , _-PO3H2 , O _{- SO3H} , _SO3H , _-COOH , N ⁺ ( _R1 )( _R2 )( _R3 ) ^An- , and being substituted by one or more identical or different radicals from -OR; said chain being optionally interrupted by one or more heteroatoms or groups selected from -O-, -S-, -C(O)-, epoxides, and their combinations such as -OC(O)- and -C(O)-O-;
- _R1 , _R2 and _R3 independently designate an alkyl radical, linear or branched in _C1 - _C20 , in particular in _C1 - _C12 , preferably in _C1 - _C6 , more preferably a methyl; _R1 , _R2 and _R3 are preferably saturated;
- An ^- designates a cosmetically acceptable anion, preferably chosen from among halides such as chlorides;
- R represents a hydrogen atom, a linear or branched alkyl radical, saturated or unsaturated in _C1 - _C6 , preferably in _C1 - _C4 , in particular a methyl, or a -C(O)-C(R _a )(R _b )-C(O)-R ₄ radical;
- R _a and R _b , identical or different, represent a hydrogen atom or a (C ₁ -C ₄ )alkyl group, preferably a hydrogen atom;
- R ₄ represents a monovalent hydrocarbon radical in C ₁ to C ₆ , linear or branched, saturated or unsaturated, preferably a (C ₁ -C ₄ )alkyl group, in particular methyl or tert-butyl, more preferably methyl;
it being understood that said compound of formula (I) contains at least two radicals -C(O)-C(R _a )(R _b )-C(O)-R ₄ ; and
ii) at least one crosslinking agent.

According to a preferred embodiment, the treatment process according to the invention further comprises the application of at least iii) a cosmetic active ingredient, to keratinous materials, in particular the skin and/or lips and/or eyelashes and/or eyebrows and/or keratinous fibers, preferably hair.

According to a preferred embodiment, the process according to the invention comprises the application (i) of at least one compound of formula (I) as defined above, its optical, geometric isomers, and/or its solvates, such as hydrates, or of a composition containing them, the application (ii) of at least one crosslinking agent and the application (iii) of at least one cosmetic active ingredient, to keratinous materials, in particular the skin and/or lips and/or eyelashes and/or eyebrows and/or keratin fibers, preferably hair.

When present, cosmetic active ingredient iii) can be applied at the same time as i) and/or ii).

According to a particular embodiment, keratinous materials, in particular skin and/or lips and/or eyelashes and/or eyebrows and/or keratinous fibers, preferably hair, may be damp or wet before application of i) and/or ii), and possibly iii). By way of example, steps i), ii) and possibly iii) may be carried out on damp skin.

According to one embodiment, the process includes the application of i), ii) and optionally iii) to moist or wet keratinous materials, in particular to skin and/or lips and/or eyelashes and/or eyebrows and/or keratinous fibers, in particular moist or wet hair.

According to another embodiment, the process includes the application of i), ii) and optionally iii) to dry keratinous materials, in particular dry skin and/or lips and/or eyelashes and/or eyebrows and/or dry keratinous fibers, in particular dry hair.

The inventors have thus found, surprisingly, that the application to keratinous materials, in particular the skin and/or lips and/or eyelashes and/or eyebrows and/or keratinous fibers, preferably hair, of ingredients i), ii), and possibly iii), makes it possible to provide deposits on keratinous materials, in particular the skin, and/or keratinous fibers, in particular hair, exhibiting good resistance to external aggressions such as water, oils in particular food, sweat and/or sebum and therefore having a very good hold over time.

Advantageously, the deposits obtained with the processes according to the invention are also very convenient. They are film-forming, non-sticky, and non-transferable.

The application of ingredients i), ii), and possibly iii), to keratinous materials, particularly on the skin and/or lips and/or eyelashes and/or eyebrows, also allows for advantageously shiny deposits.

Detailed description Definitions

For the purposes of the present invention, in the entire description, including the claims, and unless otherwise indicated:

The term " cosmetic " refers to a composition compatible with the skin, mucous membranes, and hair. The composition according to the invention is non-therapeutic.

The term “ keratinous materials ” refers in particular to the skin, mucous membranes, keratinous fibers, eyelashes and hair appendages.

The term “ keratin fibers ” refers in particular to hair, eyelashes and/or eyebrows, and preferably hair.

By " skin " we mean the entire skin of the body, and preferably the skin of the face, scalp, décolletage, neck, arms and forearms, eyelids, around the mouth or behind the ears, the crook of the elbow, the back of the knees, hands, wrists and ankles, or even more preferably, the skin of the face (in particular the forehead, nose, cheeks, chin), décolletage and neck.

A composition according to the invention comprises a physiologically acceptable medium, that is to say, one which has a pleasant colour, odor and feel and does not generate unacceptable discomforts, that is to say, tingling, pulling, redness, which may deter the user from applying this composition.

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

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

- By " fatty substance ", we mean, for the purposes of the present invention, an organic compound insoluble in water at ordinary temperature (25 °C) and atmospheric pressure (760 mm Hg) (solubility less than 5%, and preferably 1%, even more preferably 0.1%); furthermore, fatty substances are soluble in organic solvents under the same conditions of temperature and pressure, such as halogenated solvents such as chloroform, dichloromethane, inferior alcohols such as ethanol or aromatic solvents such as benzene or toluene.

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

• un radical (poly)(hydroxy)alkyle en C₁-C₆, de préférence en C₁-C₄;
• un atome d’halogène tel que chlore, fluor ou brome ;
• un groupement hydroxy ;
• un radical alcoxy en C₁-C₂; un radical (poly)-hydroxyalcoxy en C₂-C₄;
• un radical amino ;
• un radical amino substitué par un ou deux radicaux alkyle, identiques ou différents, en C₁-C₆, de préférence en C₁-C₄;
• un radical acylamino (-N(R)-C(O)-R’) dans lequel le radical R est un atome d’hydrogène ;
• un radical alkyle en C₁-C₄et le radical R’ est un radical alkyle en C₁-C₄; un radical carbamoyle ((R)₂N-C(O)-) dans lequel les radicaux R, identiques ou non, représentent un atome d’hydrogène, un radical alkyle en C₁-C₄;
• un radical alkylsulfonylamino (R’-S(O)₂-N(R)-) dans lequel le radical R représente un atome d’hydrogène, un radical alkyle en C₁-C₄et le radical R’ représente un radical alkyle en C₁-C₄, un radical phényle ;
• un radical aminosulfonyle ((R)₂N-S(O)₂-) dans lequel les radicaux R, identiques ou non, représentent un atome d’hydrogène, un radical alkyle en C₁-C₄;
• un radical carboxylique sous forme acide ou salifiée (de préférence avec un métal alcalin ou un ammonium, substitué ou non) ;
• un groupement cyano (CN) ;
• un groupement polyhalogéno(C₁-C₄)alkyle, préférentiellement le trifluorométhyle (CF₃).

- The " aryl " radicals or the aryl part of a radical can be substituted by at least one substituent attached to a carbon atom, chosen from:

• a _C1 - _C6 (poly)(hydroxy)alkyl radical, preferably _C1 - _C4 ;
• an atom of halogen such as chlorine, fluorine or bromine;
• a hydroxy group;
• an alkoxy radical in _C1 - _C2 ; a (poly)-hydroxyalkoxy radical in _C2 - _C4 ;
• an amino radical;
• an amino radical substituted by one or two alkyl radicals, identical or different, in _C1 - _C6 , preferably in _C1 - _C4 ;
• an acylamino radical (-N(R)-C(O)-R') in which the radical R is a hydrogen atom;
• an alkyl radical in C ₁ -C ₄ and the radical R' is an alkyl radical in C ₁ -C ₄ ; a carbamoyl radical ((R) ₂ NC(O)-) in which the radicals R, identical or not, represent a hydrogen atom, an alkyl radical in C ₁ -C ₄ ;
• an alkylsulfonylamino radical (R'-S(O) ₂ -N(R)-) in which the radical R represents a hydrogen atom, a C ₁ -C ₄ alkyl radical and the radical R' represents a C ₁ -C ₄ alkyl radical, a phenyl radical;
• an aminosulfonyl radical ((R) ₂ NS(O) ₂ -) in which the R radicals, identical or not, represent a hydrogen atom, an alkyl radical in C ₁ -C ₄ ;
• a carboxylic radical in acidic or salified form (preferably with an alkali metal or an ammonium, substituted or unsubstituted);
• a cyano group (CN);
• a polyhalogeno( _C1 - _C4 )alkyl group, preferably trifluoromethyl ( _CF3 ).

- A " cyclic " or " cycloalkyl " radical is a non-aromatic cyclic hydrocarbon radical, mono or polycyclic, condensed or not, containing 5 to 14 carbon atoms, which may have 1 to several unsaturations, preferably the cycloalkyl is a cyclohexyl group.

- A " heterocyclic " or " heterocycloalkyl " radical is a non-aromatic mono- or polycyclic cyclic radical, condensed or not, containing 3 to 9 links, comprising 1 to 4 heteroatoms chosen from the nitrogen, oxygen, sulfur and selenium atoms, preferably the heterocycloalkyl is chosen from epoxide, piperazinyl, piperidinyl, morpholinyl, or dithiolane.

• hydroxy,
• alcoxy en C₁-C₄, (poly)hydroxyalcoxy en C₂-C₄,
• alkylcarbonylamino (R-C(O)-NR’-) dans lequel le radical R’ est un atome d’hydrogène, un radical alkyle en C₁-C₄et le radical R est un radical alkyle en C₁-C₂, amino substitué par un ou deux groupements alkyle identiques ou différents en C₁-C₄;
• alkylcarbonyloxy (R-C(O)-O-) dans lequel le radical R est un radical alkyle en C₁-C₄, amino substitué par un ou deux groupements alkyle identiques ou différents en C₁-C₄;
• alkcoxycarbonyle (R-O-C(O)-) dans lequel le radical R est un radical alkyle en C₁-C₄, amino substitué par un ou deux groupements alkyle identiques ou différents en C₁-C₄;

- The cyclic or heterocyclic part of a non-aromatic radical can be substituted by at least one substituent attached to a carbon atom chosen from the following groups:

• hydroxy,
• C ₁ -C ₄ alkoxy, (poly)hydroxyalkoxy C ₂ -C ₄ ,
• alkylcarbonylamino (RC(O)-NR'-) in which the radical R' is a hydrogen atom, a _C1 - _C4 alkyl radical and the radical R is a _C1 - _C2 alkyl radical, amino substituted by one or two identical or different _C1 - _C4 alkyl groups;
• alkylcarbonyloxy (RC(O)-O-) in which the radical R is a _C1 - _C4 alkyl radical, amino substituted by one or two identical or different _C1 - _C4 alkyl groups;
• alkcoxycarbonyl (ROC(O)-) in which the radical R is a _C1 - _C4 alkyl radical, amino substituted by one or two identical or different _C1 - _C4 alkyl groups;

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

- A hydrocarbon chain is unsaturated when it contains one or more double bonds and/or one or more triple bonds.

- An " alkyl " radical is a saturated hydrocarbon radical, linear or branched, especially in _C1 - _C6 , preferably in _C1 - _C4 .

- An " alkoxy " radical is an alkyl-oxy radical for which the alkyl radical is a hydrocarbon radical, linear or branched, in _C1 - _C6 , preferably in _C1 - _C4 .

- A " (poly)(hydroxy)alkyl " radical designates an alkyl radical in _C1 - _C6 , preferably in _C1 - _C4 , possibly substituted by one or more hydroxy radicals, preferably substituted by 1 to 4 hydroxy groups, more particularly between 1 and 3.

- The " solvates " represent the hydrates as well as the association with linear or branched _C1 - _C4 alcohols such as ethanol, isopropanol, n-propanol.

- By " UV-A filter " we mean a chromophore made from a compound that filters (or absorbs) UV-A ultraviolet rays at a wavelength between 320 and 400 nm. We can distinguish between short UV-A filters (absorbing rays at a wavelength between 320 and 340 nm) and long UV-A filters (absorbing rays at a wavelength between 340 and 400 nm).

- By " UV-B filter " we mean a chromophore made from a compound that filters (or absorbs) UV-B ultraviolet rays at a wavelength between 280 and 320 nm.

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

- By " anhydrous composition " we mean that said composition contains a quantity of less than 5% by weight of water, preferably less than 3% by weight of water, better less than 1% by weight of water, in relation to the total weight of the composition in question, even more preferably the composition in question is free of water.

- The terms " coloring agent " and " coloring material " are equivalent.

- The expression " containing one " should be understood as synonymous with " containing at least one ", unless otherwise specified.

- The expressions " between … and … ", " includes from … to … ", " made up of … to … ", and " ranging from … to … " should be understood inclusively, unless otherwise specified.

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

Processing method

The first object of the invention is a one- or multi-step treatment process applied to keratinous materials, in particular keratin fibers or skin:
(i) at least one or more compounds of formula (I), as defined above and below, or a composition containing it or them;
(ii) at least one crosslinking agent, in particular as defined below; and
iii) possibly at least one cosmetic active ingredient, in particular as defined below.

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

According to another particular embodiment of the invention, the treatment process according to the invention comprises at least 2 steps in which ingredients i), ii), and optionally iii), are applied in separate and successive steps to the keratinous materials, it being understood that the cosmetic active ingredient(s) iii), when present, may be found together with ingredient(s) i) and/or with ingredient(s) ii).

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

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

According to another particular embodiment of the invention, the treatment process according to the invention comprises at least 2 steps in which ingredients i) and ii) are applied in separate and successive steps to the keratinous materials, it being understood that the cosmetic active ingredient(s) iii) when it is/are present, may/may be found together with ingredient(s) i) and/or with ingredient(s) ii).

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

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

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

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

According to one aspect of the invention, the process for treating keratinous materials according to the invention, implementing ingredients i), ii), and optionally iii), is a treatment for coloring keratinous fibers, preferably hair. In this embodiment, the process specifically comprises at least one cosmetic active ingredient selected from coloring materials, preferably pigments.

According to another aspect of the invention, the process for treating keratinous materials according to the invention implementing ingredients i), ii), and possibly iii), is a process for styling keratinous fibers, preferably hair.

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

According to one embodiment of the invention, the process according to the invention is a treatment process, particularly for cosmetic purposes, of keratinous materials, especially for the care and/or makeup of the skin, lips, eyelashes and/or eyebrows and/or for the care, styling and/or coloring of keratinous fibers, preferably hair, comprising the application to said keratinous materials of at least:
- a composition, referred to as "C1", comprising i) at least one compound of formula (I) as defined above and below, and possibly iii) at least one cosmetic active ingredient, in particular as defined above and below; preferably, composition "C1" does not include ii) a crosslinking agent;
- a composition, referred to as "C2", comprising i) at least one compound of formula (I), as defined above and below, ii) at least one crosslinking agent, in particular as defined below, and possibly iii) at least one cosmetic active ingredient, in particular as defined above and below; preferably, the "C2" composition does not include iii) a cosmetic active ingredient;
- a composition, referred to as "C3", comprising i) at least one compound of formula (I), as defined above and below, ii) at least one crosslinking agent, in particular as defined below, and iii) at least one cosmetic active ingredient, in particular as defined above and below;
- a composition, referred to as "C4", comprising ii) at least one crosslinking agent, in particular as defined below, and optionally iii) at least one cosmetic active ingredient, in particular as defined above and below; preferably, composition "C4" does not comprise i) at least one compound of formula (I) as defined above and below; and/or
- a composition, referred to as "C5", comprising iii) at least one cosmetic active ingredient, in particular as defined above and below; preferably, the "C5" composition does not include i) at least one compound of formula (I) as defined above and below, and does not include ii) at least one crosslinking agent;
provided that the process employs i) at least one compound of formula (I) as defined above and below, and ii) at least one crosslinking agent, and that the compositions "C1", "C2", "C3", "C4" and "C5" may be anhydrous, aqueous such as hydroalcoholic and/or comprise one or more fatty substances iv), in particular as described below.

According to one embodiment of the invention, the process according to the invention is a treatment process, particularly for cosmetic purposes, of keratinous materials, especially for the care and/or makeup of the skin, lips, eyelashes and/or eyebrows and/or for the care, styling and/or coloring of keratinous fibers, preferably hair, comprising the application to said keratinous materials of at least:
- i) at least one compound of formula (I) as defined above and below, and possibly iii) at least one cosmetic active ingredient, in particular as defined above and below;
- a composition, referred to as "C2", comprising i) at least one compound of formula (I) as defined above and below, ii) at least one crosslinking agent, in particular as defined below, and possibly iii) at least one cosmetic active ingredient, in particular as defined above and below; preferably, the "C2" composition does not include iii) any cosmetic active ingredient;
- a composition, referred to as "C3", comprising i) at least one compound of formula (I) as defined above and below, ii) at least one crosslinking agent, in particular as defined below, and iii) at least one cosmetic active ingredient, in particular as defined above and below;
- a composition, referred to as "C4", comprising ii) at least one crosslinking agent, in particular as defined below, and optionally iii) at least one cosmetic active ingredient, in particular as defined above and below; preferably, composition "C4" does not comprise i) at least one compound of formula (I) as defined above and below; and/or
- a composition, referred to as "C5", comprising iii) at least one cosmetic active ingredient, in particular as defined above and below; preferably, the "C5" composition does not include i) at least one compound of formula (I) as defined above and below and does not include ii) at least one crosslinking agent;
provided that the process employs i) at least one compound of formula (I) as defined above and below and ii) at least one crosslinking agent, in particular as defined below, and that the compositions “C2”, “C3”, “C4” and “C5” may be anhydrous, aqueous such as hydroalcoholic and/or comprise one or more fatty substances iv), in particular as described below.

According to one aspect, the process for treating keratinous materials according to the invention, in particular for the care and/or makeup of the skin, lips, eyelashes and/or eyebrows and/or for the care, styling and/or coloring of keratinous fibers, preferably hair, employs a composition, referred to as "C2", comprising i) at least one compound of formula (I), as defined above and below, ii) at least one crosslinking agent, in particular as defined below, and optionally iii) at least one cosmetic active ingredient, in particular as defined above and below, and in particular at least one coloring material, more particularly at least one pigment.

According to another aspect of the invention, the process for treating keratinous materials, in particular for the care and/or makeup of the skin, lips, eyelashes and/or eyebrows and/or for the care, styling and/or coloring of keratinous fibers, preferably hair, employs a composition, referred to as "C3", comprising i) at least one compound of formula (I), as defined above and below, ii) at least one crosslinking agent, in particular as defined above and below, and iii) at least one cosmetic active ingredient, in particular as defined below, notably selected from a) coloring agents, such as pigments, direct colorants, and mixtures thereof, b) active ingredients for the care of keratinous materials, preferably skin, c) UV filters, and d) mixtures thereof, and in particular at least one coloring agent, more particularly at least one pigment.

According to another aspect of the invention, the process for treating keratinous materials, in particular for the care and/or makeup of the skin, lips, eyelashes and/or eyebrows and/or for the care, styling and/or coloring of keratinous fibers, preferably hair, employs a composition called "C1" and a composition called "C4", said composition "C1" comprising i) at least one compound of formula (I), as defined above and below, and optionally iii) at least one cosmetic active ingredient, in particular as defined above and below, and said composition "C4" comprising ii) at least one crosslinking agent, in particular as defined below, and optionally iii) at least one cosmetic active ingredient, in particular as defined above and below.

According to another aspect, the process for treating keratinous materials, in particular for the care and/or makeup of the skin, lips, eyelashes and/or eyebrows and/or for the care, styling and/or coloring of keratinous fibers, preferably hair, employs i) at least one compound of formula (I), as defined above and below, or a composition called "C1" containing it or them and possibly comprising iii) at least one cosmetic active ingredient, in particular as defined above and below, a composition called "C4" and a composition called "C5", said composition "C4" comprising ii) at least one crosslinking agent, in particular as defined below, and possibly iii) at least one cosmetic active ingredient, in particular as defined above and below, and said composition "C5" comprising iii) at least one cosmetic active ingredient, in particular as defined above and below.

According to another aspect, the process for treating keratinous materials, in particular for the care and/or makeup of the skin, lips, eyelashes and/or eyebrows and/or for the care, styling and/or coloring of keratinous fibers, preferably hair, employs a composition called "C2" and a composition called "C5", said composition "C2" comprising i) at least one compound of formula (I) as defined above and below, ii) at least one crosslinking agent, in particular as defined below, and possibly iii) at least one cosmetic active ingredient, in particular as defined above and below, and said composition "C5" comprising iii) at least one cosmetic active ingredient, in particular as defined above and below.

According to one variant of the process of the invention, the ingredient(s) i), and optionally iii) are applied together, namely simultaneously, to the keratinous materials, in a first step, and then in a subsequent step, the ingredient(s) ii) and/or iii), are applied to the keratinous materials.

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

According to a particular embodiment of the process, in the first step, i) at least one compound of formula (I), as defined above and below, or a composition called "C1" containing it or them and possibly comprising iii) at least one cosmetic active ingredient, in particular as defined above and below, is applied to the keratinous materials, and then a composition "C4" is applied to the said keratinous materials.

According to yet another variant of the process of the invention, ingredient(s) ii) and optionally iii) is/are applied to the keratinous materials, then ingredient(s) i) and optionally iii) at least one cosmetic active ingredient, in particular as defined above, are applied to the keratinous materials. In particular, composition “C4” is applied to the keratinous materials, then i) at least one compound of formula (I), as defined above and below, or a composition called “C1” containing it/them and optionally comprising iii) at least one cosmetic active ingredient, in particular as defined above and below.

According to another variant of the method according to the invention, i) at least one compound of formula (I) as defined above and below or a composition "C1" containing it or them and possibly containing iii) is applied, and sequentially a composition "C4" containing ii) and possibly iii) is applied, preferably i) or composition "C1" being applied before composition "C4".

According to another variant of the process according to the invention, a composition "C2" containing i), ii) at least one crosslinking agent, and optionally iii) at least one cosmetic active ingredient, is applied, and sequentially a composition "C4" containing ii) at least one crosslinking agent, and optionally at least one cosmetic active ingredient iii) is applied, preferably composition "C2" being applied before composition "C4", and it being understood that the possible crosslinking agent(s) contained in composition "C2" may be identical or different from the crosslinking agent(s) contained in composition "C4", preferably the crosslinking agent(s) are different.

The compositions “C1”, “C2”, “C3”, “C4” and/or “C5” of the process according to the invention which comprise at least one fatty substance (iv), in particular at least one oil, may be in the form of a direct or reverse emulsion.

The compositions “C1”, “C2”, “C3”, “C4” and/or “C5” of the process according to the invention can therefore be applied directly as such to the keratin fibers or even be formed directly on the surface of these keratin fibers.

According to the invention, two implementation methods are distinguished, called "1-step application method" and "2-step application method".

According to one embodiment of the process of the invention, the process is carried out in one step by applying to the keratinous materials and/or keratinous fibers the composition "C2" or "C3" as defined above.

Thus, according to one embodiment, the treatment process according to the invention comprises a single step of applying composition "C2", or composition "C3", to keratinous materials and/or keratinous fibers.

The term “one-step application method” means the direct application to the target keratinous materials and/or keratinous fibers, in particular the skin, lips, eyelashes, eyebrows and/or hair, of a single composition conforming to the invention, namely composition “C2” or composition “C3”.

After application of composition "C2" or composition "C3", a durable, non-sticky deposit is advantageously obtained. The resulting deposit is also resistant to cooking oils, water, shampoo, sebum, and/or friction.

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

The term "two-step application method" refers to the successive application of two different compositions to keratinous materials and/or keratinous fibers, for example, "C1" and "C4", or "C2" and "C4", or "C3" and "C4". Preferably, "C1" then "C4", "C2" then "C4", or "C3" then "C4".

The term “2-step application method” also refers to the sequential application to keratinous materials of i) at least one compound of formula (I) as defined above and below, and of a composition “C4”, preferably i) then “C4”.

In 2-step application methods, the composition applied first, for example i) at least one compound of formula (I), or "C1", or "C2" is conventionally referred to as "base coat", and the composition(s) superimposed on it, for example "C4", are generally referred to as "top coat".

After applying the different compositions (i) at least one compound of formula (I) or "C1", and "C2" to "C5", a residual and non-sticky deposit is advantageously obtained. The deposit obtained is also resistant to edible oils, water, and shampoos.

According to a particular embodiment, compositions i) at least one compound of formula (I) or "C1", and "C2" to "C5" are applied to dry keratin materials and/or keratin fibers.

According to a particular embodiment, compositions i) at least one compound of formula (I) or "C1", and "C2" to "C5" are applied to wet or moist keratin materials and/or keratin fibers, i.e. to keratin materials and/or keratin fibers containing water on the surface.

According to a particular embodiment, the keratin materials and/or keratin fibers are dried after application of the compositions i) at least one compound of formula (I) or "C1", and "C2" to "C5", in particular after application of each different composition.

According to one aspect, the present invention relates to a process, in particular cosmetic, of keratinous materials, in particular for the care and/or makeup of the skin, lips, eyelashes and/or eyebrows and/or for the care, styling and/or coloring of keratinous fibers, preferably hair, comprising a step of applying to the keratinous fibers, a "C2" composition or a "C3" composition, in particular containing at least one coloring material, in particular as defined above, and more particularly at least one pigment.

According to another aspect, the present invention relates to a cosmetic treatment method for the care and/or makeup of keratinous materials, particularly of the skin, lips, eyelashes and/or eyebrows, and/or for the care, styling and/or coloring of keratinous fibers, preferably hair, comprising the successive application to said keratinous materials of at least:
- i) at least one compound of formula (I) as defined above and below, or of a composition called "C1" containing it or them and possibly comprising iii) at least one cosmetic active ingredient, in particular as defined above and below; then
- a composition, referred to as "C4", comprising ii) at least one crosslinking agent, in particular as defined below, and possibly iii) at least one cosmetic active ingredient, in particular as defined above and below;
at least one of the compositions "C1" and/or "C4" containing at least one colouring material, in particular as defined above and below, preferably at least one pigment, and more preferably composition "C1" includes at least one pigment.

According to another aspect, the present invention relates to a cosmetic treatment process for keratinous materials, particularly skin, lips, eyelashes and/or eyebrows and/or keratinous fibers, preferably hair, in particular for the care and/or makeup of keratinous materials and/or the care, styling and/or coloring of keratinous fibers, comprising the successive application of at least:
- i) at least one compound of formula (I) as defined above and below, or a "C1" or "C2" or "C3" composition as defined above; then
- a "C4" composition as defined previously;
provided that the process uses together or separately i) at least one compound of formula (I) as defined above and below, and that the compositions "C1", "C2", "C3" and/or "C4" may be anhydrous, aqueous such as hydroalcoholic and/or comprise one or more fatty substances iv), in particular as described below.

According to another aspect, the present invention relates to a cosmetic treatment process for keratinous materials, particularly skin, lips, eyelashes and/or eyebrows and/or keratinous fibers, preferably hair, in particular for the care and/or makeup of keratinous materials and/or the care, styling and/or coloring of keratinous fibers, comprising the successive application of at least:
- a "C2" or "C3" composition as defined above; and
- a "C4" or "C5" composition as defined above;
provided that compositions “C2” or “C3” contain at least iv) a colouring material, in particular as defined below, and/or composition “C4” or “C5” contains at least one colouring material, in particular as defined below, preferably composition “C2” or “C3” includes at least one pigment.

Compounds i): h triglyceride oils functionalized by ionic and acetoacetate functions

As indicated above, the treatment process according to the invention comprises the application to keratinous materials, in particular skin and/or lips and/or eyelashes and/or eyebrows, and/or keratinous fibers, preferably hair, of at least one or more compounds of formula (I), or a composition containing them.

Thus, the treatment process according to the invention comprises the application to keratinous materials, in particular for the care and/or makeup of the skin, lips, eyelashes and/or eyebrows and/or for the care, styling and/or coloring of keratinous fibers, preferably hair, of at least one or more compounds of formula (I), as well as their optical, geometric and/or solvate isomers, such as hydrates, or a composition containing them:

formula (I) in which:
- AK1, AK2 and AK3 independently designate a monovalent hydrocarbon chain, linear or branched, saturated or unsaturated, in _C4 - _C30 , in particular in _C6 - _C24 , preferably in _C10 - _C24 , said chain being substituted by one or more ionic groups selected from -O- _PO3H2 , _-PO3H2 , O _{- SO3H} , _SO3H , _-COOH , N ⁺ ( _R1 )( _R2 )( _R3 ) ^An- , and being substituted by one or more identical or different radicals from -OR; said chain being optionally interrupted by one or more heteroatoms or groups selected from -O-, -S-, -C(O)-, epoxides, and their combinations such as -OC(O)- and -C(O)-O-;
- _R1 , _R2 and _R3 independently designate an alkyl radical, linear or branched in _C1 - _C20 , in particular in _C1 - _C12 , preferably in _C1 - _C6 , more preferably a methyl; _R1 , _R2 and _R3 are preferably saturated;
- An ^- denotes a cosmetically acceptable anion, preferably chosen from among halides such as chlorides;
- R represents a hydrogen atom, a linear or branched alkyl radical, saturated or unsaturated in _C1 - _C6 , preferably in _C1 - _C4 , in particular a methyl, or a -C(O)-C(R _a )(R _b )-C(O)-R ₄ radical;
- R _a and R _b , identical or different, represent a hydrogen atom or a (C ₁ -C ₄ )alkyl group, preferably a hydrogen atom;
- R ₄ represents a monovalent hydrocarbon radical in C ₁ to C ₆ , linear or branched, saturated or unsaturated, preferably a (C ₁ -C ₄ )alkyl group, in particular methyl or tert-butyl, more preferably methyl;
it being understood that said compound of formula (I) contains at least two radicals -C(O)-C(R _a )(R _b )-C(O)-R ₄ ; and
- ii) at least one crosslinking agent.

The present invention also relates to a compound of formula (I) in which:
- AK1, AK2 and AK3 independently designate a monovalent hydrocarbon chain, linear or branched, saturated or unsaturated, in _C4 - _C30 , in particular in _C6 - _C24 , preferably in _C10 - _C24 , said chain being substituted by one or more ionic groups selected from -O- _PO3H2 , _-PO3H2 , O _{- SO3H} , _SO3H , _-COOH , N ⁺ ( _R1 )( _R2 )( _R3 ) ^An- , and being substituted by one or more identical or different radicals from -OR; said chain being optionally interrupted by one or more heteroatoms or groups selected from -O-, -S-, -C(O)-, epoxides, and their combinations such as -OC(O)- and -C(O)-O-;
- _R1 , _R2 and _R3 independently designate an alkyl radical, linear or branched in _C1 - _C20 , in particular in _C1 - _C12 , preferably in _C1 - _C6 , more preferably a methyl; _R1 , _R2 and _R3 are preferably saturated;
- An ^- designates a cosmetically acceptable anion, preferably chosen from among halides such as chlorides;
- R represents a hydrogen atom, a linear or branched alkyl radical, saturated or unsaturated in _C1 - _C6 , preferably in _C1 - _C4 , in particular a methyl, or a -C(O)-C(R _a )(R _b )-C(O)-R ₄ radical;
- R _a and R _b , identical or different, represent a hydrogen atom or a (C ₁ -C ₄ )alkyl group, preferably a hydrogen atom;
- R ₄ represents a monovalent hydrocarbon radical in C ₁ to C ₆ , linear or branched, saturated or unsaturated, preferably a (C ₁ -C ₄ )alkyl group, in particular methyl or tert-butyl, more preferably methyl;
it being understood that said compound of formula (I) contains at least two radicals -C(O)-C(R _a )(R _b )-C(O)-R ₄ ,
as well as its salts, isomers and/or solvates such as hydrates.

According to a preferred embodiment, the compound(s) of formula (I), as well as their optical, geometric and/or solvate isomers, such as hydrates, are such that:
- AK1, AK2 and AK3 independently designate a branched monovalent hydrocarbon chain, saturated or unsaturated, in _C10 - _C24 , said chain being substituted by one or more ionic groups selected from -O- _PO3H2 , _-PO3H2 , _{O - SO3H} , _SO3H , -COOH, N ⁺ ( _R1 )( _R2 )( _R3 ) ^An- , and being substituted by one or more identical or different radicals from -OR; said chain being optionally interrupted by one or more heteroatoms or groups selected from -O-, -S-, -C(O)-, epoxides, and their combinations such as -OC(O)- and -C(O)-O-;
it being understood that said compound of formula (I) contains at least two radicals -C(O)-C(R _a )(R _b )-C(O)-R ₄ .

In particular, the said compound(s) of formula (I), as well as their optical, geometric and/or solvate isomers, such as hydrates, are such that:
- AK1, AK2 and AK3 independently designate a branched, unsaturated monovalent hydrocarbon chain, in _C10 - _C24 , said chain being substituted by one or more ionic groups selected from -O- _PO3H2 , _-PO3H2 , O- _SO3H , _SO3H and _-COOH , and being substituted by one or more identical or different radicals from -OR; said chain being optionally interrupted by one or more heteroatoms or groups selected from -O-, -S-, -C(O)-, epoxides, and their combinations such _as -OC(O)- and -C(O)-O-;
it being understood that said compound of formula (I) contains at least two radicals -C(O)-C(R _a )(R _b )-C(O)-R ₄ .

More specifically, the said compound(s) of formula (I), as well as their optical, geometric and/or solvate isomers, such as hydrates, are such that:
- AK1, AK2 and AK3 independently designate a branched and unsaturated monovalent hydrocarbon chain, in _C10 - _C24 , said chain being substituted by one or more ionic groups chosen from -O- _PO3H2 , _-PO3H2 , O- _SO3H , _SO3H , _-COOH , and being substituted by one or more identical or different _radicals from -OR;
it being understood that said compound of formula (I) contains at least two radicals -C(O)-C(R _a )(R _b )-C(O)-R ₄ .

Preferably, the said compound(s) of formula (I), as well as their optical, geometric and/or solvate isomers, such as hydrates, are such that:
- AK1, AK2 and AK3 independently designate a branched and unsaturated monovalent hydrocarbon chain, in _C10 - _C24 , said chain being substituted by one or more ionic groups chosen from -O- _PO3H2 , _-PO3H2 , O- _SO3H , _SO3H , _-COOH , and being substituted by one or more identical or different _radicals from -OR;
it being understood that said compound of formula (I) contains at least two radicals -C(O)-C(R _a )(R _b )-C(O)-R ₄ .

More preferably, the said compound(s) of formula (I), as well as their optical, geometric and/or solvate isomers, such as hydrates, are such that:
- AK1, AK2 and AK3 independently designate a branched and unsaturated monovalent hydrocarbon chain, in C ₁₀ -C ₂₄ , said chain being substituted by one or more ionic groups chosen from -O-PO ₃ H ₂ and O-SO ₃ H and being substituted by one or more identical or different radicals from -OR;
- R ₄ represents a (C ₁ -C ₄ )alkyl group, in particular methyl;
it being understood that said compound of formula (I) contains at least two radicals -C(O)-C(R _a )(R _b )-C(O)-R ₄ .

According to another preferred embodiment, the compound(s) of formula (I), as well as their optical, geometric and/or solvate isomers, such as hydrates, are such that:
- AK1, AK2 and AK3 independently designate a monovalent _, branched, unsaturated hydrocarbon chain, in _C4 - _C30 , said chain being substituted by one or more ionic groups chosen from -O- _PO3H2 , O- _SO3H , and being substituted by one or more identical or different radicals from -OR; said chain being optionally interrupted by one or more heteroatoms or groups chosen from -O-, -S-, -C(O)-, and their combinations such as -OC(O)- and -C(O)-O-;
- R ₄ represents a (C ₁ -C ₄ )alkyl group, in particular methyl;
it being understood that said compound of formula (I) contains at least two radicals -C(O)-C(R _a )(R _b )-C(O)-R ₄ .

Preparation of compounds of formula (I)

Triglyceride oils Ionic functions and acetoacetate functions are notably obtained from ionic triglyceride oils.

In particular, these ionic triglyceride oils can be obtained by synthetic routes known to those skilled in the art.

By way of non-limiting example of the invention, the ionic triglyceride oils considered can be obtained from the synthetic routes described in the following publications: Farhadian, A., et al (2022). Sulfonated Castor Oil as an Efficient Biosurfactant for Improving Methane Storage in Clathrate Hydrates, ACS Sustainable Chemistry & Engineering, 10(30), 9921-9932; Prasad, RBN, & Rao BVXK (2017). Chapter 8 - Chemical Derivatization of Castor Oil and Their Industrial Utilization, Fatty Acids, Chemistry, Synthesis, and Applications, pages 279-303; Zhong, B., Shaw, C., Rahim, M., & Massingill, J. (2001). Novel coatings from soybean oil phosphate ester polyols, Journal of Coatings Technology, 73(915), 53-57; Wen, H., Wang, Y., Zhu, H., Jin, L., & Zhang, F. (2022) A Fluorescent Tracer Based on Castor Oil for Monitoring the Mass Transfer of Fatliquoring Agent in Leather, Materials , 15(3), 1167; Ma, Y., Zhu, X., Zhang, Y., Li, X., Chang, X., Shi, L., Lv, S., Zhang, Y. (2024). Castor oil-based adhesives: A comprehensive review, Industrial Crops and Products, Volume 209, 117924; Gaddam, K.R., & Palanisamy, A., (2016). Anionic waterborne polyurethane dispersion from maleated cotton seed oil polyol carrying ionizable groups, Colloid and Polymer Science, 294(2), p. 347-355; and Chang, P.B., Thakur, S., Mohanty, A.K., & Misra, M. (2019). Novel sustainable biobased flame retardant from functionalized vegetable oil for enhanced flame retardancy of engineering plastic, Scientific Reports, volume 9, 15971; as well as in applications US 2002/188148 and EP0283994.

Preferably, triglyceride oils of formula (I) are obtained from ionic triglyceride oils such as sulfated castor oil (RN: 8002-33-3) marketed by Zschimmer & Schwarz GmbH & Co KG) under the name Turkey Red Oil; sulfated canola (rapeseed) oil (RN: 308063-51-6) marketed by Ascent Chemicals; phosphate castor oil (RN: 447453-01-2) marketed by Phoenix Chemical, Inc under the name Phoenate COPA; even more preferably from phosphate castor oil.

According to a preferred embodiment, the process for preparing the compounds of formula (I) includes at least one reaction step of an ionic triglyceride oil of formula (II):

in which:
- AK'1, AK'2 and AK'3 independently designate a linear or branched monovalent hydrocarbon chain, saturated or unsaturated, in _C4 - _C30 , in particular in _C6 - _C24 , preferably in _C10 - _C24 , said chain being substituted by one or more ionic groups selected from -O- _PO3H2 , _-PO3H2 , O _{- SO3H} , _SO3H - _COOH , N ⁺ ( _R1 )( _R2 )( _R3 ) ^An- , and being substituted by one or more identical or different radicals from -OH; said chain being optionally interrupted by one or more heteroatoms or groups selected from -O-, -S-, -C(O)-, epoxides, and their combinations such as -OC(O)- and -C(O)-O-, in particular -S-;
- _R1 , _R2 and _R3 independently designate an alkyl radical, linear or branched in _C1 - _C20 , in particular in _C1 - _C12 , preferably in _C1 - _C6 , more preferably a methyl; _R1 , _R2 and _R3 are preferably saturated;
- An ^- designates a cosmetically acceptable anion, preferably chosen from among halides such as chlorides;
provided that said compound of formula (II) contains a) at least one ethylenic unsaturation or b) at least two hydroxy radicals or c) at least one hydroxy radical and at least one ethylenic unsaturation.

In particular, said compound of formula (II) contains a) at least two ethylenic unsaturations or b) at least two hydroxy radicals or c) at least one hydroxy radical and at least one ethylenic unsaturation.

When the compounds of formula (II) contain b) at least two hydroxy radicals, the compounds of formula (I) can be obtained in one step by reaction of said compound of formula (II).

When the compounds of formula (II) contain a) at least one ethylenic unsaturation, the compound(s) of formula (I) can be obtained in two steps.

When compounds of formula (II) contain c) both one or more hydroxy radicals and one or more ethylenic unsaturations, compounds of formula (I) can be obtained in a single step by direct (trans)esterification reaction of all or part of the hydroxy functions, as described below, if at least two hydroxy functions are present, or in two steps, consisting of a (trans)esterification reaction on all or part of the hydroxyl functions pre-existing a thiol-ene reaction or generated as a result of the thiol-ene reaction, as described below.

One-step preparation

As described previously, the process for preparing the compounds of formula (I) can be carried out in a single step from an ionic triglyceride oil of formula (II).

Thus, when the compounds of formula (II) contain at least two hydroxy radicals, the compounds of formula (I) can be obtained in one step by reaction of said compound of formula (II) and of a compound Gp-C(O)-C(R _a )(R _b )-C(O)-R ₄ , in which Gp denotes a group starting preferably from a hydroxy radical or an (C ₁ -C ₄ ) alkoxy radical, such as methoxy, ethoxy, isobutoxy or t-butoxy.

According to a preferred embodiment, Gp-C(O)-C(R _a )(R _b )-C(O)-R ₄ designates an ester selected from ethyl acetoacetate, ethyl 2-methylacetoacetate, ter-butyl acetoacetate, preferably ter-butyl acetoacetate.

In this step, all or part of the hydroxyl groups -OH of the compounds of formula (II) are transformed into radicals -OC(O)-C(R _a )(R _b )-C(O)-R ₄ .

This (trans)esterification process can be implemented according to the protocol described in Trevino, A. S., & Trumbo, D. L. (2002). Acetoacetylated castor oil in coatings applications. Progress in Organic Coatings, 44(1), 49-54.

By way of non-limiting example of the invention, the following reaction scheme can be implemented:

Multi-step preparation

As described previously, the process for preparing compounds of formula (I) can be carried out in several steps from an ionic triglyceride oil of formula (II), when the compounds of formula (II) contain at least two ethylenic unsaturations.

First step:

In a first step, all or part of the ethylenic unsaturates of the compounds of formula (II) are transformed via a thiol-ene reaction, carried out between the ethylene unsaturates and a (poly)hydroxylated thiol.

The thiol-ene reaction can be carried out from (poly)hydroxylated thiols such as linear hydroxylated thiols of formula HS-( _CH2 ) _k -OH with k being an integer, in particular an integer from 1 to 12, preferably from 1 to 6, such as 2-mercaptoethanol, 3-mercapto-1-propanol, 6-mercapto-1-hexanol, 4-mercapto-1-butanol, or such as branched hydroxylated thiols preferably having from 1 to 6 carbon atoms, such as 3-mercapto-3-methylbutanol, 3-mercapto-2-butanol, or such as polyhydroxylated thiols, preferably having from 1 to 6 carbon atoms such as 3-mercapto-1,2-propanediol HS-CH(OH) _-CH2OH .

Second step:

In a second step, the hydroxylated compounds obtained from the previous step are transesterified with a Gp-C(O)-C(R _a )(R _b )-C(O)-R ₄ compound, where Gp denotes a group preferably originating from a hydroxy radical or an (C ₁ -C ₄ ) alkoxy radical, such as methoxy, ethoxy, isobutoxy or t-butoxy, as described in Desroches, M., Caillol, S., Lapinte, V., Auvergne, R., & Boutevin, B. (2011). Synthesis of biobased polyols by thiol-ene coupling from vegetable oils. Macromolecules, 44(8), 2489–2500.

The second step allows to transform all or part of the hydroxyl groups -OH into radicals -OC(O)-C(R _a )(R _b )-C(O)-R ₄ .

By way of non-limiting example of the invention, in the case of a sulfated triglyceride oil, the following reaction scheme can be implemented:

According to a preferred embodiment, at the end of the one- or multi-step preparation processes as previously described, the compounds of formula (I) do not carry hydroxy radicals -OH.

Compounds ii): crosslinking agent

As previously stated, the treatment process according to the invention comprises the application to keratinous materials and/or keratinous fibers, preferably skin, lips, eyelashes, eyebrows and/or hair, of (i) at least one compound of formula (I) as defined previously, and (ii) at least one crosslinking agent.

For the purposes of the invention, the term "crosslinking agent", also referred to as "R", designates a compound capable of forming with at least one acetoacetate function of the 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 link,
and thus to crosslink this or these compound(s).

Preferably, the term "crosslinking agent", also called "R", designates a compound 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 crosslinking this or these compound(s).

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

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

According to one aspect, the treatment process of the invention uses a composition called "C3", in particular cosmetic for the treatment of keratinous materials and/or keratinous fibers, in particular for the care and/or makeup of the skin, lips, eyelashes and/or eyebrows and/or for the care, styling and/or coloring of keratinous fibers, preferably hair, comprising i) at least one compound of formula (I), as defined above and below, ii) at least one crosslinking agent, in particular as defined above and below, and optionally iii) at least one cosmetic active ingredient, in particular as defined above and below.

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

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

More specifically, the crosslinking agent(s) ii) suitable for the invention may be chosen from compounds with amine and/or thiol functional groups. A crosslinking agent R may also refer to a metal alkoxide.

Thus, according to a particular embodiment, the crosslinking agent(s) ii) are chosen from (poly)amine, (poly)thiol, metal alkoxides and their mixtures, preferably chosen from (poly)amine, (poly)thiol and their mixtures, and more preferably chosen from (poly)amine compounds.

By "(poly)amine and (poly)thiol compounds" we mean compounds having respectively at least one primary or secondary amine or thiol function.

Metal alkoxide compounds are defined below.

A) Polyamine compounds

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

The (poly)amine compound can in particular be chosen from among polyamine compounds having several primary and/or secondary amine groups or from among the amino alkoxysilanes, and more particularly from among the amino alkoxysilane compounds, the diamine compounds, the triamine compounds, and their mixtures.

The (poly)amine compound may be a compound comprising from 2 to 20 carbon atoms, including a non-polymeric compound; they may be acyclic or cyclic, linear or branched, saturated or unsaturated, conjugated or non-conjugated, aromatic or non-aromatic, optionally interrupted by one or more heteroatoms or groups selected from -O-, -S-, -Si(R') _2- , -N(R'')- preferably -O-, -Si(R') _2- , or their combinations such as -Si(R') ₂ -O- or -O-Si(R') _2- , with R', identical or different, representing a ( _C1 - _C4 )alkyl group such as methyl, and R'' representing a hydrogen atom or a ( _C1 - _C4 )alkyl group, preferably a hydrogen atom.

By "non-polymer compound" we mean a compound that is not directly obtained by a polymerization reaction of monomers.

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

According to a particular embodiment of the invention, the (poly)amine compound(s) are monoamine, namely they contain a single primary and/or secondary amine group, preferably primary ( _NH2 ).

The (poly)amine compound(s) can be chosen from among the amino alkoxysilanes, in particular those with the formula _R'1 Si( _OR'2 ) _z ( _R'3 ) _x, in which:

- _R'1 is a _C1 - _C6 hydrocarbon chain, linear or branched, saturated or unsaturated, cyclic or acyclic, substituted by a group chosen from among the primary amine groups _NH2 or secondary -N(H)R, with R representing a _C1 - _C4 alkyl, an aryl, a benzyl substituted by an amino group or by a _C1 - _C4 aminoalkyl group; _R'1 may be interrupted in its chain by a heteroatom (O, S, NH) or a carbonyl group C(O), _R'1 being linked to the silicon atom directly via a carbon atom,

- _R'2 and _R'3 , whether identical or different, represent a ( _C1 - _C6 )alkyl group, linear or branched,

- z denotes an integer from 1 to 3, and

- x represents an integer ranging from 0 to 2,

with z + x = 3.

In particular, _R'1 is an acyclic chain. Preferably, _R'1 is a linear or branched, saturated or unsaturated _C1 - _C6 hydrocarbon chain substituted with an amine group _-NH2 or -N(H)R, where R represents a _C1 - _C6 alkyl, a _C3 - _C6 cycloalkyl, or a _C6 aromatic. More preferably, _R'1 is a linear, saturated _C1 - _C6 hydrocarbon chain substituted with an amine group _NH2 . Even more preferably, _R'1 is a linear, saturated _C2 - _C4 hydrocarbon chain substituted with an amine group _NH2 .

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

In particular, _R'3 represents an alkyl group comprising 1 to 4 carbon atoms; preferably, _R'3 represents a linear alkyl group comprising 1 to 4 carbon atoms, and more preferably, _R'3 represents the methyl or ethyl group. Preferably, z is equal to 3.

In particular, the (poly)amine compound(s) are chosen from among the amino alkoxysilanes having only one primary and/or secondary amine group, preferably primary ( _NH2 ), such as 3-aminopropyltriethoxysilane (APTES), 3-aminoethyltriethoxysilane (AETES), 3-aminopropylmethyldiethoxysilane, N-(2-aminoethyl)-3-aminopropyltriethoxysilane, 3-(m-aminophenoxy)propyltrimethoxy-silane, p-aminophenyltrimethoxysilane, and N-(2-aminoethylaminomethyl)-phenethyltrimethoxysilane.

Preferably, the (poly)amine compound(s) are chosen from 3-aminopropyltriethoxysilane (APTES), 3-aminoethyltriethoxysilane (AETES), 3-aminopropylmethyldiethoxysilane, and N-(2-aminoethyl)-3-aminopropyltriethoxysilane, and more preferably 3-aminopropyltriethoxysilane (APTES), in particular that marketed by Sigma Aldrich.

The (poly)amine compound may also be chosen from among amine polymers, in particular having a weight average molecular weight ranging from 500 g.mol ^-1 to 1,000,000 g.mol ^-1 , preferably ranging from 500 g.mol ^-1 to 500,000 g.mol ^-1 , and preferably ranging from 500 g.mol ^{- 1} to 100,000 g.mol ^-1 .

According to a particular embodiment of the invention, the (poly)amine compound(s) are monoamine and selected from polydialkylsiloxanes, in particular those of formula (III):

H ₂ N-ALK-Si(R' ₂ )(R' ₃ )-O-[ Si(R' ₂ )(R' ₃ )-O] _n - Si(R' ₂ )(R' ₃ )-R' ₄ (III)

formula (III) in which:

- ALK represents a ( _C1 - _C4 )alkylene group, linear or branched, preferably linear, such as propylene,

- _R'2 and _R'3 , whether identical or different, preferably identical, represent an ( _C1 - _C4 ) alkyl group such as methyl, and

- _R'4 represents a ( _C1 - _C6 ) alkyl group, linear or branched, preferably at _C4 , such as n-butyl; n represents an integer greater than or equal to 2; preferably the value of n is such that the average molecular weight by weight of the polydimethylsiloxane ranges from 500 to 3000 g.mol ^-1 . Examples of polydimethylsiloxanes(III) include those sold under the names "MCR-A11" and "MCR-A12" by the company Gelest.

According to a particular embodiment of the invention, the (poly)amine compound(s) are diaminized, namely they contain two primary and/or secondary amine groups, preferably primary ( _NH2 ).

• ALK[(O-ALK’)_m-NH₂]₂(IV)

More specifically, they are chosen from compounds with formulas (IV) or (V):

• ALK[(O-ALK') _m -NH ₂ ] ₂ (IV)

• H₂N-ALK-Si(R’)₂-[O-Si(R’)₂]_m-O-Si(R)₂-ALK’-NH₂(V)

Or

• H ₂ N-ALK-Si(R') ₂ -[O-Si(R') ₂ ] _m -O-Si(R) ₂ -ALK'-NH ₂ (V)

formulas (IV) and (V) in which:

- ALK and ALK', whether identical or different, represent a ( _C1 - _C6 )alkylene group, linear or branched, preferably linear, such as propylene,

- R', whether identical or different, represents a ( _C1 - _C4 )alkyl group, such as methyl,

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

Examples of compounds with formula (V) include those sold under the names "DMS-A11", "DMS-A12", "DMS-A15", "DMS-A21", "DMS-A31", "DMS-A32" and "DMS-A35" by the company Gelest.

The (poly)amine compound(s) which are diamined are particularly the diamine polyethers, notably of the formula _H2N -ALK-O-[ALK'-O] _m -ALK''- _NH2 with ALK, ALK' and ALK'', identical or different, representing a ( _C1 - _C6 )alkylene group, linear or branched, and m representing an integer greater than or equal to 0, such as 4,7,10-trioxa-1,13-tridecanediamine or the compounds known under the reference Jeffamine from the Huntsman company, and more particularly polyethylene glycol and/or polypropylene glycol α,ω-diamine (with amine function at the end of the chain) such as those sold under the names Jeffamine D-230, D-400, D-2000, D-4000, ED-600, ED-9000, ED-2003.

According to a particular embodiment of the invention, the (poly)amine compound(s) are triamine, namely they contain three primary and/or secondary amine groups, preferably primary ( _NH2 ). More particularly, they are chosen from triamine polyethers, in particular those of formula ALK'''[(O-ALK') _m - _NH2 ] ₃ , with ALK' as defined above and ALK''' representing a trivalent ( _C1 - _C6 )alkylene group, linear or branched, and m representing an integer greater than or equal to 0.

As (poly)amine compounds which are triamine, triamine polyethers are particularly cited, and in particular polyethylene glycol and/or polypropylene glycol α, ω-diamine (with amine function at the end of the chain) such as those sold under the name Jeffamine T-403.

According to another particular embodiment of the invention, the (poly)amine compound(s) comprise more than three primary and/or secondary amine groups, preferably primary ( _NH2 ).

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

Preferably, polyamine compounds are chosen from chitosans (especially poly(D-glucosamine)), 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 in particular chosen from poly(alkylene ( _C2 - _C5 )imines), and preferably polyethyleneimines and polypropyleneimines, in particular poly(ethyleneimine), in particular that sold under reference 408700 by Aldrich Chemical or under the trade name Lupasol by BASF, in particular with a molecular weight between 1200 and 25000; poly(allylamine), in particular that sold under reference 479136 by Aldrich Chemical; polyvinylamines and their copolymers in particular with vinylamides, in particular vinylamine/vinylformamide copolymers such as those marketed under the name ^Lupamin® 9030 by BASF; polyamino acids having _NH2 groups such as polylysine, in particular that sold by JNC Corporation (formerly Chisso); amino dextran, in particular that sold by CarboMer Inc; polyvinyl amino alcohol, in particular that sold by CarboMer Inc; acrylamido( _C1 - _C6 )alkylamine-based copolymers, in particular acrylamidopropylamine-based copolymers; and poly(D-Glucosamine), for example, sold under the reference Kionutrime ^CSG® by Kytozyme.

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

R _a -Si(R _b )(R _c )-O-[Si(R _b )(R _c )-O] _m -[Si(ALK ¹ -NH ₂ )(R _a )-O] _n -Si(R _b )(R _c )-R _a (VI)

formula (VI) in which:

- _Ra , whether identical or different, represents a hydroxyl or ( _C1 - _C4 )alkyl group,

- _Rb and _Rc , identical or different, preferably identical, represent a ( _C1 - _C4 )alkyl group, such as methyl,

- ALK ¹ represents a (C ₁ -C ₆ )alkylene group, linear or branched, possibly interrupted by an N(H) group,

- m and n are integers greater than or equal to 1, preferably m and n are such that the average molecular mass by weight of the compound of formula (VI) goes from 1,000 g.mol ^-1 to 500,000 g.mol ^-1 .

According to a preferred variant, formula (VI) is such that _Ra , _Rb , and _Rc represent a methyl group, ^ALK1 represents a propylene group, n and m are such that the values of n and m are such that the weight-average molecular weight of polydimethylsiloxane ranges from 1,000 g.mol ^-1 to 55,000 g.mol ^-1 .

Examples of polydimethylsiloxanes of formula (VI) include those sold under the names "AMS-132", "AMS-152", "AMS-162", "AMS-163", "AMS-191" and "AMS-1203" by the company Gelest.

According to another variant, formula (VI) is such that Ra _represents a hydroxyl or ( _C1 - _C4 ) alkyl group, such as methyl, ^ALK1 represents a ( _C5 - _C6 ) alkylene group substituted by an NH group, preferably ^ALK1 represents -( _CH2 ) ₃ -N(H)-( _CH2 ) _2- , and m and n are such that the weight-average molecular mass of the compound of formula (VI) ranges from 5,000 g.mol ^-1 to 500,000 g.mol ^-1 .

Other examples of amino polymers that can be cited include polytetrahydrofuran (or polytetramethylene glycol) α,ω-diamine, and polybutadiene α,ω-diamine.

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 selected from (poly)amine compounds, in particular selected from chitosans, aminoalkoxysilanes, polydimethylsiloxanes comprising primary amine groups at the end of the chain or on side chains, amodimethicones, polyglucosamines, spermidine, and mixtures thereof.

More preferably, the composition comprises a crosslinking agent R selected 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 preferably selected from poly(D-Glucosamine), 3-aminopropyltriethoxysilane (APTES), 3-aminoethyltriethoxysilane (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 called "( poly) mercapto ".

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

In a preferred embodiment, the (poly)thiol compound is siliconized, that is to say, it comprises one or more thiol groups, and furthermore at least one siloxane chain.

In one particular embodiment, the (poly)thiol compound is inorganic. Polythiol silicones are an example.

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

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

According to one embodiment of the invention, the (poly)thiol compound(s) is/are organic, non-polymer(s), and of formula (VII) below, as well as their solvates, such as their hydrates:

L(SH) _q (VII)

formula (VII) in which:

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

- L denotes a multivalent (at least divalent) group, in particular comprising between 1 and 500 carbon and/or silicon atoms, more particularly between 2 and 40 carbon and/or silicon atoms, even more particularly between 3 and 30 carbon and/or silicon atoms, preferably between 6 and 20 carbon atoms, linear or branched, saturated or unsaturated, or (hetero)cyclic, saturated or unsaturated; L being optionally interrupted and/or terminated by one or more heteroatoms or groups selected from O, S, N, Si, C(X), and their combinations such as -O-, -OC(X)-, -N(R)-C(X)-, -Si(R _c )(R _d )-O- with R representing a hydrogen atom or a (C ₁ -C ₆ )alkyl group, such as methyl; and/or L being optionally substituted by one or more groups chosen from: -N(R _a )R _b , and -(X') _a -C(X)-(X'') _b -R _a ; with X, X' and X'', identical or different, representing an oxygen atom, a sulfur atom, or an N(R _b ) group ; a and b being 0 or 1, preferably the sum of a + b is 1 ; R _a and R _b , identical or different, represent a hydrogen atom, or a (C ₁ -C ₆ ) alkyl group, or aryl(C ₁ -C ₄ )alkyl group, such as benzyl, preferably R _a and R _b represent a hydrogen atom ; and R _c and R _d , identical or different, represent a (C ₁ -C ₆ ) alkyl, aryl(C ₁ -C ₄ )alkyl or (C ₁ -C ₆ ) alkoxy group.

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

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

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

Preferably, L denotes a multivalent _C8 - _C18 radical, in particular a linear one. Preferably, the fat-soluble polythiol is a _C8 - _C18 dithiol, in particular a linear one. Preferably, the _C8 - _C18 chain is a hydrocarbon chain, that is, one composed of carbon and hydrogen. In particular, the fat-soluble polythiol is a linear _C8 - _C16 diol, in particular a _C10 - _C14 diol. Examples of (poly)thiol compounds with formula (VII) include, in particular, 1,8-octanedithiol, 1,10-decanedithiol, 1,12-dodecanedithiol, 1,14-tetradecanedithiol, 1,16-hexadecanedithiol, and 1,18-octadecanedithiol. Preferably, 1,10-decanedithiol, 1,12-dodecanedithiol and/or 1,14-tetradecanedithiol are used, preferably 1,12-dodecanedithiol.

According to another particular embodiment of the invention, the (poly)thiolated compound(s) is/are chosen from thiolated alkoxysiloxanes, such as those of formula (VII’) below:

R' ₁ -Si(OR' ₂ )z(R' ₃ ) _x (VII')

formula (VII') in which:
- _R'1 is a _C1 - _C12 hydrocarbon chain, linear or branched, saturated or unsaturated, cyclic or acyclic, substituted by one or more groups selected from the following: thiol, aryloxy, arylthio, arylamino, the aryl group being substituted by one or more thiol groups, or thiol( _C1 - _C6 )alkyl, preferably thiol( _C1 - _C6 )alkyl; and _R'1 is optionally interrupted in its hydrocarbon chain by one or more heteroatoms such as O, S, N, a carbonyl group C(O), or their combination such as -C(O)-O- ester, or -C(O)-N(H)- amide, _R'1 being linked to the silicon atom directly via a carbon atom,
- _R'2 and _R'3 , whether identical or different, represent an alkyl group, linear or branched, comprising from 1 to 6 carbon atom(s), preferably from 1 to 4 carbon atom(s), such as methyl,
- z denotes an integer from 1 to 3, and
- x represents an integer ranging from 0 to 2,
with z + x = 3.

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

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

Preferably, _R'1 is an acyclic chain, in particular _R'1 is a _C1 - _C6 hydrocarbon chain, linear or branched, saturated or unsaturated, preferably saturated, substituted by one or more thiol groups, preferably substituted by a thiol group.

Preferably, _R'1 is a linear saturated _C1 - _C6 hydrocarbon chain substituted with a thiol group, and _R'2 represents an alkyl group comprising 1 to 4 carbon atoms,

Preferably, _R'3 represents an alkyl group comprising 1 to 4 carbon atoms.

Preferably, z is equal to 3.

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

(R ¹ O)(R ² )(R ³ )Si-[CH(R ⁴ )] _t -[N(R' ⁴ )-L ¹ ] _p -SH (VIII)

formula (VIII) in which:
- p is equal to 0 or 1;
- t is an integer between 1 and 4, preferably 2;
- R ¹ represents a (C ₁ -C ₆ )alkyl radical;
- ^R2 and ^R3 , identical or different, preferably identical, are chosen from an ( _C1 - _C6 ) alkyl group, in particular _C1 - _C4 , such as methyl, and an ( _C1 - _C6 ) alkoxy group, in particular ( _C1 - _C4 ) alkoxy, such as methoxy;
- ^R4 and ^R'4 , whether identical or different, represent a hydrogen atom, or an ( _C1 - _C6 ) alkyl group, such as methyl;
- L ¹ represents a linear or branched divalent, saturated hydrocarbon radical, in C ₁ -C ₂₀ .

According to a particular embodiment of the invention, the thiolated alkoxysiloxane compounds are chosen from those of the following formula (VIII’):

(R' ¹ O)(R' ² )(R' ³ )Si-CH(R ⁴ )-CH(R ⁵ )-(L ² ) _q -SH (VIII')
formula (VIII') in which:
- q is equal to 0 or 1;
- X represents an oxygen or sulfur atom, preferably sulfur;
- R' ¹ denotes an alkyl (C ₁ -C ₆ ) radical;
- R' ² and R' ³ , identical or different, preferably identical, are chosen from a (C ₁ -C ₆ )alkoxy group, in particular in C ₁ -C ₄ , and a (C ₁ -C ₆ )alkyl radical;
- R ⁵ represents a hydrogen atom or an alkyl group in C ₁ -C ₄ possibly substituted by an amino, thiol or hydroxy group;
- R ⁴ represents a hydrogen atom or an alkyl group in C ₁ -C ₄ , in particular methyl;
- L ² represents a divalent hydrocarbon group, linear or branched, saturated at C ₁ -C ₂₀ , possibly interrupted by a heteroatom such as -N(H)-, and/or possibly substituted by one or more hydroxy, thiol or amino groups.

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

Preferably, the thiolated alkoxysilane(s) are chosen from 2-(triethoxysilyl)-ethanethiol (18236-15-2) and 3-(triethoxysilyl)-1-propanethiol (14814-09-6).

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

Poly(poly)thiol compounds can be homopolymers, copolymers, star, comb, brush, and dendritic thiol-retaining compounds. The polymers can be of natural origin, such as polysaccharides and polypeptides, or synthetic, such as acrylics, polyesters, and polyglycols. The thiol motifs can be present as terminal or dangling groups.

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

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

POLY(SH) _q (IX)
formula (IX) in which:
- q is greater than or equal to 2, preferably greater than or equal to 3;
- POLY denotes a polymeric radical, preferably carbon- or silicon-based; POLY being optionally interrupted by one or more heteroatoms or groups selected from O, S, N, Si, C(X), and their combinations such as -O-, -OC(X)-, -N(R)-C(X)-, -Si(R _c )(R _d )-O- with R representing a hydrogen atom or a (C ₁ -C ₆ )alkyl group such as methyl; and/or POLY being optionally substituted by one or more halogen atoms, or a group selected from _Ra (R _b )N- and -(X') _a -C(X)-(X'') _{b -Ra} ; X, X' and X'', identical or different, represent an oxygen atom, a sulfur atom, or an N(R _b ) group; a, and b being 0 or 1, preferably the sum of a + b is 1; R _a and R _b , identical or different, represent a hydrogen atom, or a (C ₁ -C ₁₀ )alkyl, or aryl(C ₁ -C ₄ )alkyl group, such as benzyl, preferably R _a and R _b represent a hydrogen atom; and R _c and R _d , identical or different, represent a (C ₁ -C ₁₀ )alkyl, aryl(C ₁ -C ₄ )alkyl or (C ₁ -C ₁₀ )alkoxy group.

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

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

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

According to one embodiment of the invention, the polythiol compound is a polymeric compound of formula (IX) in which q denotes an integer greater than or equal to 2, and POLY denotes a carbon and/or silicon polymeric radical, preferably silicon, POLY being able to further contain one or more heteroatoms selected from O, N, S and/or one or more functions selected from the (thio)ester, (thio)ketone, (thio)amide, (thio)urea, (thio)carbamate functions, and/or be substituted by one or more (C ₁ -C ₁₀ )alkyl, linear or branched, (C ₁ -C ₁₀ )alkoxy, linear or branched groups, it being understood that when POLY is substituted, the thiol functions may be borne by the substituent(s).

The average molecular weight in molar weight of polythiol polymer compounds, such as those of formula (IX), is generally between 500 and 400,000 g.mol ^-1 , preferably between 500 and 150,000 g.mol ^-1 .

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

HS-L ⁴ -Si(R ^a )(R ^b )-O-[Si(R ^a )(R ^b )-O] _n -Si(R ^a )(R ^b )-L ⁵ -SH (X)
formula (X) in which:
- R ^a and R ^b , identical or different, preferably identical, represent an (C ₁ -C ₄ ) alkyl group, such as methyl, (C ₁ -C ₄ ) alkoxy, such as methoxy, aryl, such as phenyl, aryloxy, such as phenoxy, aryl(C ₁ -C ₄ )alkyl, such as benzyl, or aryl(C ₁ -C ₄ )alkoxy, such as benzoxy, preferably (C ₁ -C ₄ ) 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 average molecular weight by weight of the polyorganosiloxane ranges from 500 to 55,000 g.mol ^-1 ; particularly n is an integer ranging from 1 to 100, preferably ranging from 5 to 50, and preferably ranging from 10 to 30, and
- ^L4 and ^L5 , identical or different, preferably identical, represent a hydrocarbon chain comprising from 1 to 100 carbon atoms, saturated or unsaturated, linear or branched, possibly cyclic, possibly interrupted by one or more heteroatoms, such as oxygen, sulfur or nitrogen, in particular oxygen, in particular represent a covalent bond, a ( _C1 - _C6 )alkylene, ( _C1 - _C6 )alkylene-oxy, oxy-( _C1 - _C6 )alkylene, ( _C1 - _C6 )alkylene-oxy( _C1 - _C6 )alkylene, ( _C1 - _C6 )alkylene-oxy( _C1 - _C6 )alkylenoxy or oxy( _C1 - _C6 )alkylene-oxy( _C1 - _C6 )alkylene, preferably a ( _C1 - _C6 )alkylene, ( _C1 - _C6) )alkylene-oxy, oxy-( _C1 - _C6 )alkylene, or ( _C1 - _C6 )alkylene-oxy( _C1 - _C6 )alkylene.

Preferably, the (poly)thiol compounds are polythiol polyorganosiloxanes, more preferably polythiol polydimethylsiloxanes, in particular chosen from those of formula (XI):
HS-L ⁴ -Si(CH ₃ ) ₂ -O-[Si(CH ₃ ) ₂ -O] _n -Si(CH ₃ ) ₂ -L ⁵ -SH (XI)
formula (XI) in which:
- ^L4 and ^L5 are as defined previously in formula (XI), in particular ^L4 and ^L5 represent a ( _C1 - _C6 )alkylene, ( _C1 - _C6 )alkylene-oxy, oxy-( _C1 - _C6 )alkylene, or ( _C1 - _C6 )alkylene-oxy( _C1 - _C6 )alkylene group, more preferably a divalent group selected from _-R2- , _-OR2- , -R2-O-, _-R2 - _OR2- , preferably _{-R2 - OR2-} , with _R2 representing a linear or branched ( _C2 - _C6 )alkylene group, preferably linear, such as ethylene or propylene, preferably propylene; and
- n is such as defined in formula (XI).

Examples of polythiol compounds of formula (XI) include mercaptosiloxanes or thiol siloxanes, in which the thiol functions are located at the end of the chain, marketed by SHIN-ETSU under the reference X-22-167B and mercaptosiloxane, in which the mercapto functions are pendant, marketed by SHIN-ETSU under the reference KF-2001, or polydimethylsiloxanes in which the thiol functions are located at the end of the chains by thio-n-propyl groups, 80-120 marketed by Gelest under the name DMS – SM 21.

Preferably, polythiol compounds are polyorganosiloxanes containing thiol groups on side chains such as those of formula (XII):
R ^a -Si(R ^b )(R ^d )-O-[Si(R ^a )(R ^b )-O] _m -[Si(R ^b )(ALK ₁ -SH)-O] _n -Si(R ^b )(R ^d )-R ^a (XII)
formula (XII) in which:
- ^Ra , and ^Rb , are such as defined in formula (X) and ^Rd is such as defined for ^Ra and ^Rb , preferably ^Ra , ^Rb , and ^Rd , identical, represent a ( _C1 - _C6 ) alkyl group, such as methyl;
- R ^d can also represent a (C ₁ -C ₆ ) alkyl group substituted by a (C ₁ -C ₄ )alkylamino or amino, or thiol group, preferably (C ₁ -C ₄ ) alkyl, such as methyl;
- ALK ₁ represents a divalent hydrocarbon chain comprising from 1 to 100 carbon atoms, saturated or unsaturated, linear or branched, possibly cyclic, possibly interrupted by one or more heteroatoms such as oxygen, sulfur or nitrogen, in particular oxygen, a (thio)carbonyl group C(X) with X representing O, or S, or their combinations such as -O-, -OC(O)- or -C(O)-O-, preferably ALK ₁ represents a (C ₁ -C ₆ ) alkylene group, more preferably (C ₁ -C ₄ ) alkylene, such as propylene;
- n and m, identical or different, represent an integer greater than 2, and more particularly the values of m and n are such that the average molecular weight by weight of said polyorganosiloxane is between 1000 and 55,000 g.mol ^-1 .

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

Polythiol compounds include polydimethylsiloxanes with at least two thiol groups, such as, for example, 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 thiol PAMAMs.

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

C) Metal alkoxides

• M-(OR₁)_n(XIII_a)
• R-M-(OR₁)_n-1 (XIII_b)
• (R₁O)_n-1-M-R’’-M’-(OR₁’)_{n ’ -1}(XIII_c)
• R-M(R’)-(OR₁)_n-2(XIII_d)

According to a particular embodiment, the crosslinking agent R is a compound selected from metal alkoxides of formulas (XIII_has), (XIII_b), (XIII_c) and (XIII_d) the following, and their mixtures:

• M-(OR ₁ ) _n (XIII _a )
• R-M-(OR₁)_n-1 (XIII_b)
• (R ₁ O) _n-1 -M-R''-M'-(OR ₁ ') _{n ' -1} (XIII _c )
• RM(R')-(OR ₁ ) _n-2 (XIII _d )

formulas (XIII _a ), (XIII _b ), (XIII _c ) and (XIII _d ) in which:
- M and M', identical or different, represent an atom chosen from among the alkaline earth metals, the transition metals, the lanthanide family metals, the post-transition metals such as aluminium or tin and the metalloids, such as boron, preferably the transition metals, such as Ti, and the post-transition metals, such as aluminium;
- n and n' represent respectively the valences of the atoms represented by M and M';
- _R1 and _R1 ', identical or different, represent a hydrocarbon group, linear or branched, saturated or unsaturated, having from 1 to 30 carbon atoms, preferably from 1 to 6 carbon atoms, said hydrocarbon group possibly being interrupted by 1 to 20 heteroatoms chosen from O, N, S and P, in particular O or N, and/or said hydrocarbon group possibly being substituted by one or more hydroxy or carbonyl groups;
- R and R', identical or different, represent a hydrogen atom or a hydrocarbon group, linear, branched, acyclic or cyclic, saturated or unsaturated, having from 1 to 30 carbon atoms, preferably from 2 to 20 carbon atoms, possibly interrupted by 1 to 20 heteroatoms chosen from O, N, S and/or P, in particular O or N and/or said hydrocarbon group possibly being substituted by one or more hydroxy or carbonyl groups;
- R'' represents -O-, -N(R2)-, -S- or a divalent hydrocarbon group, linear, cyclic or branched, saturated or unsaturated, having from 1 to 30 carbon atoms, preferably from 2 to 20 carbon atoms, possibly interrupted by 1 to 20 heteroatoms chosen from O, N, S and P, especially O or N, with R2 representing a hydrocarbon group, linear, cyclic or branched, saturated or unsaturated, having from 1 to 30 carbon atoms, preferably from 2 to 20 carbon atoms.

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

Preferably, the organometallic compound(s) are chosen from alkoxides of formula (XIII _a ) as defined above. According to this preferred embodiment, the organometallic compound(s) are more particularly chosen from alkoxides of formula (XIII _a ), in which M represents an atom chosen from among the transition metals, the lanthanide metals, the post-transition metals, such as aluminum, tin, the metalloids, such as boron, or the alkaline earth metals, such as magnesium or calcium; n represents the valence of the atom represented by M; R ₁ represents a saturated, linear or branched hydrocarbon group, having 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 alkoxides of formula (XIII _a ), in which M represents an atom chosen from transition metals, such as zirconium or titanium, lanthanide metals, post-transition metals, such as aluminum, tin, metalloids, such as boron, and alkaline earth metals, such as magnesium, preferably M represents a titanium atom; n represents the valence of the atom represented by M, in particular 1, 2, 3 or 4, in particular 4; R ₁ represents a methyl, ethyl, 2-ethylhexyl, propyl, isopropyl, n-butyl, isobutyl or t-butyl group.

According to a further preferred embodiment, the organometallic compound(s) are selected from zirconium ethoxide (Zr( _OC₂H₅ ) _₄ ), zirconium propoxide (Zr( _{OCH₂CH₂CH₃} ) _₄ ), zirconium isopropoxide (Zr(OCH( _{CH₃)₂ ) ₄} ), zirconium butoxide (Zr( _{OCH₂CH₂CH₂CH₃} ) _₄ ), zirconium tert-butoxide (Zr( _OC ( _CH₃ ) _₃ ) _₄ ), titanium ethoxide (Ti( _OC₂H₅ ) _₄ ), titanium propoxide ₍ Ti( _{OCH₂CH₂CH₃} ) _₄ ), titanium isopropoxide (Ti( _{OCH ( CH₃} ) _₂ ) _{₄ )} , and titanium butoxide (Ti( _OCH₃ ) _{₄ ) . 2} CH ₂ CH ₂ CH ₃ ) ₄ ), titanium tert-butoxide (Ti(OC(CH ₃ ) ₃ ) ₄ ), titanium 2-ethylhexyloxide (Ti(OCH ₂ CH(C ₂ H ₅ )(CH ₂ ) ₃ CH ₃ ) ₄ ), and mixtures thereof, more preferably chosen from zirconium propoxide, titanium propoxide, titanium butoxide and mixtures thereof.

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

According to a preferred embodiment, the crosslinking agent is chosen from compounds A) (poly)amines and B) (poly)thiols, and preferably from compounds A) (poly)amines.

In particular, said (poly)amine compounds A) are selected from a) chitosans, such as poly(D-Glucosamine), b) diamine polyethers, particularly polyethylene glycol α,ω-diamine (with an amine function at the chain end), c) triamine polyethers, such as Polyetheramine (or jeffamine), d) aminoalkoxysilanes, such as APTES, and e) polydialkylsiloxanes comprising primary amine groups at the chain end or on side chains, particularly polydimethylsiloxanes comprising primary amine groups, such as bis(3-aminopropyl)-terminated poly(dimethoxysiloxane) (PDMS- _diNH2 ) and amodimethicones comprising amine groups on side chains such as bis-cetearyl amodimethicone, particularly that marketed by Momentive Performance Materials, f) the polyamine compounds _NH2- alk- _NH2 , in which alk denotes a divalent hydrocarbon chain in _C2 - _C20 , possibly interrupted by one or more heteroatoms chosen from -O-, -N(R)- with R denoting a hydrogen atom or a _C1 - _C4 alkyl radical, such as spermidine.

According to a preferred embodiment, said (poly)amine compounds A) are selected from a) chitosans, such as poly(D-Glucosamine), c) triamine polyethers, such as Polyetheramine (or jeffamine), e) polydialkylsiloxanes comprising primary amine groups at the end of the chain or on side chains, particularly polydimethylsiloxanes comprising primary amine groups, such as bis(3-aminopropyl)-terminated poly(dimethoxysiloxane) (PDMS- _diNH2 ) and amodimethicones comprising amine groups on side chains such as bis-cetearyl amodimethicone, in particular that marketed by Momentive Performance Materials, and f) _NH2 -alk- _NH2 polyamine compounds, in which alk denotes a _C2 - _C20 hydrocarbon divalent chain optionally interrupted by one or more selected heteroatoms among -O-, -N(R)- with R denoting a hydrogen atom or a _C1 - _C4 alkyl radical, such as spermidine or 4,7,10-Trioxa-1,13-tridecanediamine.

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

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

A) (Poly)amine compounds selected from:

ia) chitosans such as poly(D-Glucosamine),

ib) diamine polyethers, in particular α,ω-diamine polyethylene glycols, with an amine function at the end of the chain,

ic) triamine polyethers, in particular polyetheramine (or jeffamine),

id) aminoalkoxysilanes, in particular APTES,

ie) the polyamine compounds NH2 _- alk- _NH2 , in which alk denotes a divalent hydrocarbon chain in _C2 - _C20 , possibly interrupted by one or more heteroatoms selected from -O-, -N(R)- with R denoting a hydrogen atom or a _C1 - _C4 alkyl radical, in particular spermidine and 4,7,10-Trioxa-1,13-tridecanediamine, and

if) polydialkylsiloxanes comprising primary amine groups at the end of the chain or on side chains, in particular polydimethylsiloxanes comprising primary amine groups, more particularly poly(dimethoxysiloxane) terminated by bis(3-aminopropyl) (PDMS-diNH ₂ ) and amodimethicones comprising amine groups on side chains, more particularly bis-cetearyl amodimethicone;

B) (poly)thiol compounds selected from:

iia) thiol-group polydialkylsiloxanes, and

iib) alkoxysilanes with thiol functions,

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

R ^a -Si(R ^b )(R ^d )-O-[Si(R ^a )(R ^b )-O] _m -[Si(R ^b )(ALK ₁ -SH)-O] _n -Si(R ^b )(R ^d )-R ^a (XII)
formula (XII) in which:
- R ^a and R ^b , identical or different, preferably identical, represent a (C ₁ -C ₄ )alkyl group, in particular methyl, an (C ₁ -C ₄ )alkoxy group, in particular methoxy, an aryl group, in particular phenyl, an aryloxy group, in particular phenoxy, an aryl(C ₁ -C ₄ )alkyl group, in particular benzyl, or an aryl(C ₁ -C ₄ )alkoxy group, in particular benzoxy, and preferably a (C ₁ -C ₄ )alkyl group, more preferably methyl,
- R ^d represents a ( _C1 - _C4 )alkyl group, in particular methyl, an ( _C1 - _C4 )alkoxy group, in particular methoxy, an aryl group, in particular phenyl, an aryloxy group, in particular phenoxy, an aryl( _C1 - _C4 )alkyl group, in particular benzyl, an aryl( _C1 - _C4 )alkoxy group, in particular benzoxy, or a ( _C1 - _C6 )alkyl group substituted by a ( _C1 - _C4 )alkylamino, amino, or thiol group, and preferably a ( _C1 - _C4 )alkyl group, more preferably methyl,
and preferably R ^a , R ^b , and R ^d , are identical and represent a (C ₁ -C ₆ )alkyl group, more preferably methyl,
- ALK ₁ represents a divalent hydrocarbon chain comprising from 1 to 100 carbon atoms, saturated or unsaturated, linear or branched, possibly cyclic, possibly interrupted by one or more heteroatoms, such as oxygen, sulfur or nitrogen, in particular oxygen, a (thio)carbonyl group C(X) with X representing O or S, or their combinations, in particular -O-, -OC(O)- or -C(O)-O-, preferably ALK ₁ represents a (C ₁ -C ₆ )alkylene group, more preferably (C ₁ -C ₄ )alkylene, even more preferably propylene,
- n and m, whether identical or different, represent an integer greater than 2, and in particular the values of m and n are such that the average molecular weight by weight of said polyorganosiloxane is between 1000 and 55,000 g.mol ^-1 ; and
C) Metal alkoxides selected from: zirconium ethoxide (Zr( _OC₂H₅ ) _₄ ), zirconium propoxide (Zr( _{OCH₂CH₂CH₃} ) _₄ ), zirconium isopropoxide (Zr( _OCH ( _CH₃ ) _₂ ) _{₄ )} , zirconium butoxide (Zr( _{OCH₂CH₂CH₂CH₃ ) ₄} ), zirconium tert-butoxide (Zr(OC( _CH₃ ) _₃ ) _{₄ )} , titanium ethoxide (Ti( _OC₂H₅ ) _₄ ), titanium propoxide (Ti( _{OCH₂CH₂CH₃} ) _₄ ), titanium isopropoxide (Ti( _OCH ( _CH₃ ) _{₂ )₄ ) , titanium} butoxide ( _{Ti ( OCH₂CH₂CH₂CH₃ ) ₄ )} ), _titanium tert-butoxide (Ti(OC(CH3) ₃ ) _{4 )} , titanium ₂ -ethylhexyloxide (Ti(OCH2CH( _C2H5 )( _CH2 ) _3CH3 ) _{4 )} , and mixtures thereof, more preferably chosen from zirconium propoxide, titanium propoxide, titanium butoxide and mixtures thereof.

active ingredients in skincare

According to a particular embodiment, the process of the invention uses one or more active ingredients for the care of keratinous materials, in particular skin, lips, eyelashes and/or eyebrows and/or keratinous fibers, in particular hair.

Preferably, the cosmetic agent(s) iii) are chosen from:
a) coloring materials, in particular selected from pigments, direct colorants and mixtures thereof,
b) active ingredients for the care of keratin fibers, preferably hair fibers,
c) UV filters, and
d) their mixtures;
preferably the cosmetic agent(s) iii) are chosen from a) coloring materials, preferably chosen from pigments, direct colorants and their mixtures, more preferably the pigment(s) are chosen from carbon black, iron oxides, in particular yellow, red and black and iron oxide coated micas, triarylmethane pigments, in particular blue and violet, in particular BLUE 1 LAKE, azo pigments, in particular red, more particularly D&C RED 7, the alkali metal salt of lithol red, in particular the calcium salt of lithol red B, and
even more preferentially among red iron oxides, yellow iron oxides and azo pigments, especially red ones, more particularly D&C RED 7.

More specifically, in the process of the invention, according to one embodiment, at least one of the compositions "C1", "C2", "C3", "C4" or "C5" used comprises one or more active ingredients, preferably at a concentration of at least 0.01% by weight, relative to the total weight of the composition in question. In particular, the active ingredient may be at least one hydrophilic and/or one lipophilic active ingredient, and preferably a hydrophilic active ingredient.

The term “hydrophilic active” refers to a water-soluble or water-dispersible active capable of forming hydrogen bonds.

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

In particular, in the process of the invention, according to one embodiment, at least one of the compositions "C1", "C2", "C3", "C4" or "C5" used comprises a moisturizing agent (also called a humectant). Preferably, the active ingredient is a moisturizing agent, and in particular is glycerin (glycerol).

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

Keratin fiber care actives

According to a particular embodiment, the process of the invention uses b) one or more active ingredients for the care of keratin fibers, in particular hair.

More specifically, in the process of the invention, according to one embodiment, at least one of the compositions "C1", "C2", "C3", "C4" or "C5" used comprises one or more keratin fiber conditioning agents, preferably at a concentration of at least 0.01% by weight relative to the total weight of the composition in question. In particular, the keratin fiber conditioning agent may be at least one hydrophilic and/or one lipophilic agent, and preferably a hydrophilic conditioning agent.

The term “hydrophilic active” refers to a water-soluble or water-dispersible active capable of forming hydrogen bonds.

The cosmetic active ingredient(s) for hair care can be chosen from among those having an action on the barrier function, antioxidant active ingredients, moisturizing active ingredients, sebum regulating active ingredients, active ingredients intended to combat the effects of pollution, antimicrobial or bactericidal active ingredients, perfumes, vitamins and their derivatives, including their esters, in particular tocopherol (vitamin E) and its esters (such as tocopherol acetate), and their mixtures.

Among the active ingredients in the care of keratin fibers, we can mention in particular antioxidants, moisturizing agents, and sebum-regulating agents.

The active ingredient(s) for the care of keratin fibers may in particular be present in the composition containing them, 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 filters

According to one embodiment of the process of the invention, at least one of the compositions "C1", "C2", "C3", "C4" or "C5" implemented includes, as a cosmetic active ingredient, at least one UV filter.

The UV filter(s) is/are a/are UV filter(s) commonly used in cosmetics.

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

The UV filters suitable for the invention can be of different types.

They can be lipophilic, hydrophilic, or insoluble organic.

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

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

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

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

In particular, the UV filter(s) are selected from bis-resorcinyl triazine derivatives, dibenzoylmethane derivatives, benzylidene camphor derivatives, and mixtures thereof. Organic UV filters may also be selected from anthranilics; cinnamic derivatives; salicylic derivatives; benzophenone derivatives; phenyl benzotriazole derivatives; benzalmalonate derivatives, including those cited in US patent 5,624,663; phenyl benzimidazole derivatives; imidazolines; 4,4-diarylbutadiene derivatives; bis-benzoazolyl derivatives, as described in patents EP 6,693,230 and US 2,463,264; and p-aminobenzoic acid (PABA) derivatives. Methylene bis-(hydroxyphenyl benzotriazole) derivatives, as described in US applications 5,237,071, US 5,166,355, GB 2303549, DE 19726,184 and EP 893,119; benzoxazole derivatives, as described in patent applications EP 0,832,642, EP 1,027,883, EP 1,300,137 and DE 10162844; filter polymers and filter silicones such as those described in particular in application WO 93/04665; α-alkylstyrene derivative dimers such as those described in patent application DE 19855649; 4,4-Diarylbutadienes as described in applications EP 0 967 200, DE 19746654, DE 19755649, EP 1 008 586, EP 1 133 980 and EP 133 981; merocyanine derivatives such as those described in applications WO 04006878, WO 05058269 and WO 06032741 and mixtures thereof.

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

The UV filter(s) can be mineral UV filters, which are generally pigments. These pigments can be coated or uncoated.

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

According to a particular embodiment, compositions "C1" to "C5" are devoid of mineral UV filters.

According to a particular embodiment, the quantity of the mineral UV filter(s) present in compositions "C1", "C2", "C3", "C4" or "C5" can range from 0.01 to 20% by weight, relative to the total weight of the composition containing them. For example, it ranges from 1 to 15% by weight, relative to the total weight of the composition.

According to a particular embodiment, at least one of the compositions "C1" to "C5" further comprises one or more organic UV filters and one or more mineral UV filters.

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

Preferably, the process for treating keratin fibers, preferably hair, and the compositions "C1", "C2", "C3", "C4" or "C5" implement or include one or more coloring materials selected from pigments, direct dyes and their mixtures, preferably pigments; more preferably the pigment(s) of the invention are selected from carbon black, iron oxides in particular yellow, red and black and micas coated with iron oxide, triarylmethane pigments in particular blue and violet such as BLUE 1 LAKE, azo pigments in particular red such as D&C RED 7 alkali metal salt of lithol red such as the calcium salt of lithol red B, even more preferably red iron oxides, yellow iron oxides and azo pigments in particular red such as D&C RED 7.

Fatty phase – Fatty substances

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

In particular, at least one of the compositions "C1", "C2", "C3", "C4" or "C5" implemented in the process of the invention contains an oily phase.

In particular, at least one of the compositions "C1", "C2", "C3", "C4" or "C5", implemented in the process of the invention comprises one or more fatty substances, distinct from compounds i), in particular one or more oils, preferably volatile.

By " oil " we mean a liquid fat at room temperature (20 °C) and atmospheric pressure (760 mm Hg).

The term " hydrocarbon oil " refers to an oil formed essentially, or even composed, of carbon and hydrogen atoms, and possibly oxygen and nitrogen atoms, and containing no 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) iv) is/are chosen from volatile oils, in particular:

- hydrocarbon oils having 8 to 16 carbon atoms, in particular _C8 - _C16 branched alkanes, in particular isoalkanes, more particularly isoalkanes (also called isoparaffins), preferably _C13 - _C16 isoparaffin, isododecane, isodecane, isohexadecane, for example oils sold under the trade names Isopars or Permetyls, alone or in mixtures, preferably isododecane (also called 2,2,4,4,6-pentamethylheptane), linear alkanes, in particular _C11 - _C16 , alone or in mixtures, in particular hexane, decane, undecane, tridecane, isoparaffins in particular n-dodecane ( _C12 ) and n-tetradecane ( _C14 ), the undecane-tridecane mixture, the mixtures of n-undecane (C ₁₁ ) and n-tridecane (C ₁₃ ), and their mixtures as well as the mixtures of n -undecane (C ₁₁ ) and n -tridecane (C ₁₃ ), and the non-aromatic, volatile C ₅ -C ₁₂ cyclic alkanes;

- short-chain esters having a total of 3 to 8 carbon atoms, in particular ethyl acetate, methyl acetate, propyl acetate, n-butyl acetate;

- hydrocarbon carbonate oils of structure R' ₁ -OC(O)-O-R' ₂ in which R' ₁ and R' ₂ independently designate a linear, branched or cyclic C ₄ -C ₈ alkyl group, preferably a C ₄ -C ₈ alkyl group, advantageously, more preferably chosen from dibutyl carbonate or dipentyl carbonate;

- ether oils of formula R ₁ -OR ₂ , in which R ₁ and R ₂ designate, independently of each other, a linear, branched or cyclic C ₄ -C ₈ alkyl group, preferably a C ₄ -C ₈ alkyl group;

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

more preferably the volatile oil(s) iv) are chosen from among the _C8 - _C16 alkanes, in particular branched, preferably isododecane.

In particular, at least one of the compositions "C1", "C2", "C3", "C4" or "C5" used in the process according to the invention comprises one or more non-volatile oil(s), preferably chosen from:
- non-volatile fluorinated oils, in particular chosen from fluorinated polyethers, fluorosilicone oils, fluorinated silicones;
- non-volatile silicone oils, in particular chosen from the following non-volatile silicones with the following INCI names: dimethicone, dimethiconol, trimethyl pentaphenyl trisiloxane, tetramethyl tetraphenyl trisiloxane, diphenyl dimethicone, trimethylsiloxyphenyl dimethicone, phenyltrimethicone, diphenylsiloxy phenyl trimethicone, and their mixtures;
- non-volatile non-polar hydrocarbon oils, in particular selected from linear or branched compounds, of mineral or synthetic origin: i) paraffin oil; ii) squalane, isoeicosane; iii) mixtures of linear, saturated hydrocarbons, more particularly in _C15 - _C28 , in particular mixtures whose INCI names are ( _C15 - _C19 )alkane, ( _C18 - _C21 )alkane, ( _C21 - _C28 )alkane; iv) polybutenes, hydrogenated or not; v) polyisobutenes, hydrogenated or not, preferably hydrogenated; vi) polydecenes, hydrogenated or not; vii) decene/butene copolymers, butene/isobutene copolymers and viii) their mixtures;
- non-volatile polar hydrocarbon oils that can be chosen from:

(i) Fatty alcohols, saturated, unsaturated, linear or branched, in _C10 - _C26 , preferably mono-alcohols; in particular, _C10 - _C26 alcohols are fatty alcohols, preferably branched when they comprise at least 16 carbon atoms; preferably, the fatty alcohol comprises from 10 to 24 carbon atoms, and more preferably from 12 to 22 carbon atoms, in particular lauryl, isostearyl, oleic alcohol, 2-butyloctanol, 2-undecyl pentadecanol, 2-hexyldecyl alcohol, isocetyl alcohol, octyldodecanol and mixtures thereof;

ii) triglycerides consisting of esters of fatty acids and glycerol, in particular whose fatty acids can have chain lengths ranging from C ₄ to C ₃₆ , and especially from C ₁₈ to C ₃₆ , these oils being linear or branched, saturated or unsaturated; by way of examples, one can cite in particular heptanoic or octanoic triglycerides, caprylic/capric acid triglycerides; vegetable oils such as wheat germ, sunflower, grapeseed, sesame, corn, apricot kernel, castor, shea, avocado, olive, soybean, sweet almond, palm, rapeseed, cottonseed, hazelnut, macadamia, jojoba, alfalfa, poppy, pumpkin, squash, blackcurrant, evening primrose, millet, barley, quinoa, rye, safflower, candlenut, passionflower, rosehip, peanut, coconut, argan, and kaya oils; the liquid fraction of shea butter and the liquid fraction of cocoa butter; and mixtures thereof;

iii) linear aliphatic hydrocarbon esters of formula R-C(O)-OR’ in which R-C(O)-O- represents the carboxylic acid remainder comprising from 2 to 40 carbon atoms, and R’ represents a hydrocarbon chain containing from 1 to 40 carbon atoms, aliphatic hydrocarbon esters of alkylene glycol, in particular ethylene glycol or propylene glycol; the total number of carbon atoms being in particular at least 10; in particular selected from isoamyl laurate, cetostearyl octanoate, isopropyl myristate, isopropyl palmitate, isopropyl stearate or isostearate, ethyl palmitate, 2-ethylhexyl palmitate, isostearyl isostearate, octyl stearate, isostearyl heptanoate, octanoates, decanoates or ricinoleates of alcohols or polyalcohols such as propylene glycol dioctanoate, cetyl octanoate, tridecyl octanoate, ethyl 2-hexyl palmitate, alkyl benzoate, polyethylene glycol diheptanoate, propylene glycol diethyl 2-hexanoate and mixtures thereof, hexyl laurate, neopentanoic acid esters such as isodecyl neopentanoate, isotridecyl neopentanoate, isostearyl neopentanoate, octyl-2-docecyl neopentanoate, isononanoic acid esters, in particular isononyl isononanoate, isotridecyl isononanoate, octyl isononanoate, oleyl erucate; lauroyl isopropyl sarcosinate, diisopropyl sebacate, isocetyl stearate, isodecyl neopentanoate, isostearyl behenate, myristyl myristate;

(iv) hydroxylated esters, in particular polyglycerol-2 triisostearate;

(v) aromatic esters, in particular tridecyl trimellitate, _C12 - _C15 alcohol benzoate, 2-phenyl ethyl ester of benzoic acid, butyl octyl salicylate;

vi) linear fatty acid esters having a total number of carbons ranging from 35 to 70, in particular pentaerythrityl tetrapelargonate;

vii) fatty alcohol or _C24 - _C28 branched fatty acid esters, in particular triisoarachidyl citrate, pentaerythrityl tetraisononanoate, glyceryl triisostearate, glyceryl tridecyl-2-tetradecanoate, pentaerythrityl tetraisostearate, polyglyceryl-2 tetraisostearate or pentaerythrityl tetradecanoate;

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

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

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

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

xii) their mixtures;

- Non-volatile carbonate oils may be chosen from carbonates of the formula _R8- OC(O) _-OR9 , with _R8 and _R9 , identical or different, representing an alkyl chain from _C4 to _C12 , and preferably from _C6 to _C10 , linear or branched; the carbonate oils may be dicaprylyl carbonate (or dioctyl carbonate), di(ethyl-2-hexyl) carbonate, dipropylheptyl carbonate, dibutyl carbonate; di-neopentyl carbonate; dipentyl carbonate; dineoheptyl carbonate; di-heptyl carbonate; di-isononyl carbonate; or di-nonyl carbonate; and preferably dioctyl carbonate;

- oils called non-volatile ether oils of formula _R1 - _OR2 in which _R1 and _R2 independently designate a linear, branched, or cyclic _C6 - _C24 alkyl group, preferably a _C6 - _C18 alkyl group, and preferably a _C8 - _C12 alkyl group. It may be preferable for _R1 and _R2 to be identical. Examples of linear alkyl groups include hexyl, heptyl, octyl, nonyl, decyl, undodyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, eicosyl, behenyl, docosyl, tricosyl, and tetracosyl groups. Examples of branched alkyl groups include 1,1-dimethylpropyl, 3-methylhexyl, 5-methylhexyl, ethylhexyl, 2-ethylhexyl, 5-methyloctyl, 1-ethylhexyl, 1-butylpentyl, 2-butyloctyl, isotridecyl, 2-pentylnonyl, 2-hexyldecyl, isostearyl, 2-heptylundecyl, 2-octyldodecyl, 1,3-dimethylbutyl, 1-(1-methylethyl)-2-methylpropyl, 1,1,3,3-tetramethylbutyl, 3,5,5-trimethylhexyl, 1-(2-methylpropyl)-3-methylbutyl, and a group 3,7-dimethyloctyl, and a 2-(1,3,3-trimethylbutyl)-5,7,7-trimethyloctyl group. Examples of cyclic alkyl groups include cyclohexyl, 3-methylcyclohexyl, 3,3,5-trimethylcyclohexyl, dilaury ether, diisostearyl ether, dioctyl ether, nonylphenyl ether, dodecyl dimethyl butyl ether, cetyl dimethyl butyl ether, cetyl isobutyl ether, and mixtures thereof.

Preferably, the non-volatile oil(s) is/are chosen from among the polyisobutenes, hydrogenated or not, preferably hydrogenated, in particular the non-volatile compounds of the Parléam ^® range; mixtures of C ₁₅ -C ₁₉ alkane, and from among the linear aliphatic hydrocarbon esters of formula RC(O)-OR' in which RC(O)-O represents a carboxylic acid remnant comprising from 2 to 40 carbon atoms, and R' represents a hydrocarbon chain containing from 1 to 40 carbon atoms, as defined above, in particular isononyl isononanoate.

More preferably, the process of the invention uses one or more hydrocarbon oils having 8 to 16 carbon atoms, and in particular _C8 - _C16 branched alkanes, in particular iso-alkanes, preferably _C13 - _C16 isoparaffin, isododecane, isodecane, isohexadecane, alone or in mixtures, and more preferably isododecane.

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

In particular, the quantity of oil(s), distinct from the compounds i), in at least one of the compositions "C1", "C2", "C3", "C4" or "C5"", implemented in the process according to the invention, ranges from 1 to 99% by weight, relative to the total weight of the composition, more particularly from 2 to 98% by weight, preferably from 3 to 97%, better from 5 to 96% by weight, relative to the total weight of the composition.

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

According to yet another embodiment, at least one of the compositions "C1", "C2", "C3", "C4" or "C5"", implemented in the process according to the invention, contains a mixture of fatty substances v) distinct from the compounds i), and selected from mixtures of at least one volatile oil, preferably hydrocarbon, and at least one non-volatile oil, such as octyldodecanol.

Water-soluble solvent

According to a particular embodiment, the process of the invention further employs at least one water-soluble solvent and optionally water.

In particular, the water-soluble solvent(s) may be used in amounts ranging from 5 to 50% by weight, in particular from 10 to 40% by weight, preferably from 20 to 35% by weight of water-soluble solvent, relative to the total weight of the composition.

In the present invention, "water-soluble solvent" refers to a compound that is liquid at room temperature and miscible with water (miscibility in water greater than 50% by weight at 25°C and atmospheric pressure).

The water-soluble solvents that can be used in the process of the invention may also be volatile.

Among the water-soluble solvents that can be used, we can mention in particular lower monoalcohols having 1 to 6 carbon atoms such as ethanol and isopropanol, preferably ethanol.

Compositions

Another object of the invention is compositions, in particular cosmetics, containing at least one compound selected from compounds of formula (I) as described above, as well as their salts, isomers and/or solvates such as hydrates.

According to a particular embodiment, the process for treating keratinous materials and/or keratinous fibers, preferably hair, according to the invention uses water. Thus, according to this variant, at least one of the compositions "C1" to "C5" used in the process of the invention comprises water. According to this variant, compositions "C1", "C2", "C3", "C4", and/or "C5" are aqueous or hydroalcoholic compositions.

According to a preferred embodiment, the process for treating keratin fibers, preferably hair, according to the invention does not use water. Thus, according to this variant, compositions "C1", "C2", "C3", "C4" and/or "C5" are anhydrous compositions.

According to a particular embodiment, at least one of the compositions "C1", "C2", "C3", "C4" and/or "C5" comprise an isododecane/ethanol mixture, in particular in a volume ratio between 1/99 and 99/1, more particularly between 5/95 and 95/5.

According to a particular embodiment, at least one of the compositions "C1", "C2", "C3", "C4" or "C5" may be in the form of a water-in-oil emulsion or an oil-in-water emulsion.

According to a particular embodiment, the compositions “C1”, “C4” or “C5” may be in anhydrous form, water-in-oil emulsion or oil-in-water emulsion.

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

According to another particular embodiment, composition "C4" comprises water. In particular, composition "C4" comprises water, and optionally at least one volatile or involatile oil, and/or at least one _C1 - _C4 alcohol such as ethanol or isopropanol, and/or at least one involatile oil.

The compositions “C1” to “C5” implemented in the process of the invention may further comprise one or more solvents, distinct from water.

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

According to this embodiment, the composition "C1", "C2", "C3", "C4" and/or "C5" implemented in the process of the invention comprises one or more solvents, preferably one or more polar and/or protic solvents, other than water.

Preferably, the composition "C1", "C2", "C3", "C4" and/or "C5" implemented in the process of the invention comprises at least one polar and/or protic solvent chosen from monoalcohols having 2 to 6 carbon atoms, in particular chosen from ethanol, propanol, n-butanol, isopropanol, isobutanol, tert-butanol, pentanol, hexanol, preferably n-butanol or ethanol, and even more preferably ethanol.

According to one embodiment, the composition "C1", "C2", "C3", "C4" and/or "C5" implemented in the process of the invention comprises one or more solvents distinct from water in a content of less than 95% by weight, more preferably less than 92% by weight, relative to the total weight of the composition.

According to one embodiment, the composition "C2" or "C3" or "C4" is anhydrous.

According to another embodiment, composition "C4" is aqueous.

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

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

The compositions “C1”, “C2”, “C3”, “C4” or “C5” implemented in the process of the invention may further comprise one or more adjuvants commonly used in cosmetics, in particular chosen from thickeners, film-forming agents, gelling agents, trace elements, softeners, sequestrants, perfumes, alkalizing or acidifying agents, dispersing agents, preservatives, fillers, surfactants, anti-hair loss agents, anti-dandruff agents, free radical scavengers, propellants, polar additives, polymers, or mixtures thereof.

Another object of the invention is a composition, called "C3", in particular cosmetic, comprising i) at least one compound of formula (I), as defined above, ii) at least one crosslinking agent, in particular as defined above, and iii) at least one cosmetic active, in particular as defined above, preferably chosen from: a) coloring materials, preferably chosen from pigments, direct colorants and their mixtures, and more preferably from pigments.

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

A “C1”, “C2”, “C3”, “C4” or “C5” composition is generally suitable for application on keratinous materials and/or keratinous fibers, in particular application on skin, lips, eyelashes, eyebrows and/or hair, and therefore generally comprises a physiologically acceptable medium, i.e. compatible with keratinous materials and/or fibers, in particular human keratinous materials such as skin, lips, eyelashes and eyebrows and human keratinous fibers such as hair.

Preferably, it should be a cosmetically acceptable medium, that is to say, one which has a pleasant colour, smell and feel and does not generate unacceptable discomforts, such as tingling or pulling, which may deter the user from applying this composition.

According to a particular embodiment, a composition "C1", "C2", "C3", "C4" or "C5" is presented in the form of a hair product, in particular a hair coloring product or a styling product, especially one devoid of coloring material, such as a hairspray, or a so-called "styling" product of the mousse or gel type.

Kit

According to yet another aspect, the present invention also relates to a kit or device, particularly a cosmetic one, with several compartments comprising:
- at least one compartment containing i) at least one compound of formula (I) as defined above, and possibly iii) at least one cosmetic active ingredient, in particular as defined above, in particular comprising composition "C1" as defined above;
- at least one compartment separate from the one containing i) and containing ii) at least one crosslinking agent, in particular as defined above, and possibly iii) at least one cosmetic active ingredient, in particular as defined above, in particular comprising composition "C4" as defined above; and
- optionally, at least one compartment separate from those containing i) and ii), and containing iii) at least one cosmetic active ingredient, in particular as defined above, identical or different from that/those possibly contained in the compartments comprising i) and ii).

Preferably, the compartment comprising at least i), in particular a “C1” composition, does not include a crosslinking agent ii).

Preferably, the compartment comprising at least one crosslinking agent ii), in particular a "C4" composition, does not contain i) a compound of formula (I).

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

Methods and Measures Skin application a) One-step protocol

The compounds of formula (I) with acetoacetate functional groups, and 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 Maprecos Bioskin-type vitro support (Bioskin plate #10) (elastomer skin-simulating support) using a film applicator (wet thickness 100 µm). The deposit is left to dry for 24 hours.

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

b) Two-step protocol

A first composition, called the "base coat", is applied to a Bioskin-type vitro substrate from Maprecos (Bioskin plate #10) (a skin-simulating elastomer substrate) using a film puller (wet thickness 100 µm). The deposit is left to dry for 24 hours.

After this first step, a second composition, called "top coat", is applied in the same way.

The deposit is left to dry for 24 hours.

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

Tape resistance

A piece of tape (3M ^Scotch® Magic™ 810; 19 mm x 5 cm) is applied to the deposit. A weight of approximately 1070 g is applied to the tape for 30 seconds. The tape is then removed and placed on a microscope slide to observe the result. This evaluates the film's adhesion to the substrate.

Resistance to olive oil/sebum/water

0.5 mL of olive oil, sebum, or water is applied to the formulation film. After 5 minutes, the olive oil, sebum, or water is removed by 15 swipes with a cotton ball. The film's deterioration following contact with the aggressor droplet is then observed.

Resistance is assessed according to the following scale:

+++: no damage to the deposit, which is as it was originally;

++: a little bit of transfer but the deposit is as it was originally;

+: the deposit is slightly altered and some transfer is observed;

0: the deposit is completely degraded and there is a lot of transfer onto the cotton.

Hair application

The hair coloring evaluation protocol is detailed below:

The assessments are conducted according to two different protocols: in 1 or 2 step(s), each on strands of natural hair that are 90% white.

a) One-step protocol

The compounds of formula (I) with acetoacetate functional groups and 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 strands of dry, natural hair that is 90% white, at a rate of 1 g of composition per gram of strand.

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

The strands of hair are then combed and blow-dried for 3 minutes.

The hair strands are left at room temperature for 18 hours at 80% relative humidity. The hair is colored evenly and intensely.

b) Two-step protocol

A first composition, called a "base coat," is applied to strands of dry, natural hair that is 90% white, at a rate of 0.5 g of the composition per gram of strand. The strands are then combed. This coating is applied to the keratinous materials and then left to set for 30 minutes at room temperature (25°C).

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

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

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

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

Shampoo Protocol

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

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

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

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

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

Permanence Protocol

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

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

The persistence of the colour is evaluated 24 h after the last application of the formula composition (I) for the 1-step protocol, or after the application of the "Top Coat" for the 2-step protocol, by the colour difference ΔE between the coloured strands before shampooing, then after having undergone 3 or 5 shampoos according to the protocol described above.

The lower the ΔE value, the more the color resists shampooing.

The value of ΔE is calculated according to the following equation:

In this equation, L*a*b* represent the values measured after hair coloring and after shampooing, and L ₀ *a ₀ *b ₀ * represent the values measured after hair coloring but before shampooing.

Example 1: Synthesis of ' a l ' one-step acetoacetate-functional phosphate oil

The synthesis of a phosphate oil with acetoacetate function is carried out in a single step and is represented by the following preparation scheme:

In a 250 mL round-bottom flask equipped with a magnetic stir bar and a distillation column, 50 g of phosphated castor oil (marketed by Phoenix Chemicals under the name Phoenate Copa) and 19.47 g of tert-butyl acetoacetate are introduced. The reaction mixture is heated in an oil bath at a temperature of 140–150 °C for 3 hours. It is then heated in a rotary evaporator at 150 °C under continuous vacuum.

NMR analysis shows the functionalization of the oil.

Example 2: Synthesis of ' a l ' two-step phosphate oil with acetoacetate function

The synthesis of a phosphate oil with acetoacetate function is carried out in two steps and is represented by the following preparation diagrams:

First step:

In a 250 mL flask equipped with a reflux condenser and a magnetic stir bar, 20 g of phosphated castor oil (marketed by Phoenix Chemicals under the name Phoenate Copa), 32 g of thioglycerol, 0.97 g of 2-hydroxy-2-methylprophenophenone, and 200 mL of ethyl acetate are introduced. The reaction mixture is degassed for 5 minutes under argon gas and then irradiated under a 100 W UV lamp at 365 nm for 8 hours. The reaction mixture is then washed three times with saturated NaCl water, and the organic phase is separated, dried over _MgSO₄ , and then concentrated under vacuum. The solvent, as well as traces of thiol and 2-hydroxy-2-methylprophenophenone, are removed by distillation under reduced pressure before the second synthesis step.

Second step:

In a 250 mL round-bottom flask fitted with a distillation apparatus and under magnetic stirring, 17 g of phosphated castor oil with grafted thioglycerol groups, obtained from the first step, and 13 g of tert-butyl acetoacetate are introduced. The reaction mixture is heated in an oil bath at a temperature of 140–150 °C for 2 hours. The reaction mixture is then heated in a rotary evaporator at 150 °C under continuous vacuum.

Example 3: Preparing formulas A and B

Formulas A, outside the scope of the invention, and B, according to the invention, are prepared from the contents indicated in Table 1 below. The contents are expressed as a percentage by weight, relative to the total weight of the composition.

Compositions A and B are prepared by simply mixing the ingredients of phase 1 using a Speed Mixer (a mixing device that uses centrifugal force) for 2 minutes at 2,500 rpm and at room temperature. The ingredients of phase 2 are then added, and the mixture is blended manually and used directly.

Example 4 One-step skin application of formulas A and B

Formulas A and B are applied according to the one-step skin application protocol described previously. Deposits are evaluated according to the olive oil, sebum, and water resistance protocols described previously.

The evaluation results are summarized in the table below:

It appears that the application of composition B according to the process of the invention makes it possible to obtain an improved sebum retention, and a very significantly improved oil and water retention compared to the application of composition A, which, moreover, does not form a film.

Therefore, by applying composition B according to the process of the invention, a deposit resistant to daily chemical aggressions is obtained.

Example 5: Preparing formulas C to F

Formulas C and E, outside the scope of the invention, and D and F, according to the invention, are prepared from the contents indicated in Table 3 below. The contents are expressed as a percentage by weight, relative to the total weight of the composition.

The "Base Coat" compositions are prepared in a manner similar to composition B, by simply mixing all the ingredients detailed in Table 3, except for Jeffamine T403 or Spermidine, using a Speed Mixer (a mixing device that uses centrifugal force) for 2 minutes at 2,500 rpm and at room temperature. Jeffamine T403 or Spermidine is then added and the mixture is blended manually.

The "Top Coat" compositions are prepared by simply mixing the ingredients detailed in Table 3 using a Speed Mixer (a mixing device that uses centrifugal force) for 2 minutes, at 3,500 rpm and at room temperature.

Example 6 Two-step skin application of formulas C to F

Formulas C through F are applied according to the two-step skin application protocol described previously. Deposits are evaluated according to the olive oil, sebum, water, and tape resistance protocols described previously.

The evaluation results are summarized in Table 4 below:

It appears that the application of compositions D and F according to the process of the invention makes it possible to obtain an improved resistance to olive oil, water and sebum, compared to the application of composition C, which does not form a film, and to the application of composition E. It also appears that compositions D and F are adherent to the substrate, unlike compositions C and E.

Therefore, by applying compositions D and F according to the process of the invention, a deposit resistant to daily chemical aggressions is obtained, forming a film that adheres to the Bioskin type support.

Example 7: Preparation of formulas H and I

Formulas H, outside the scope of the invention, and I, according to the invention, are prepared from the contents indicated in Table 5 below. The contents are expressed as a percentage by weight, relative to the total weight of the composition.

Example 8 One-step hair application of formulas H and I

Formulas H and I are applied according to the one-step capillary application protocol described previously.

The evaluation results are summarized in Table 6 below:

Hair strands colored according to the invention with composition I exhibit a significantly lower residual color compared to composition H and a ΔE of less than 5.5. It therefore appears that the application of formula I according to the process of the invention makes it possible to obtain very good color residual color after three successive shampoos.

Claims (20)

Process for treating, in particular for cosmetic purposes, keratinous materials, especially for the care and/or makeup of the skin, lips, eyelashes and/or eyebrows and/or for the care, styling and/or coloring of keratinous fibers, preferably hair, comprising the application to said keratinous materials, in one or more successive steps, of at least:
- i) one or more compound(s) of formula (I), as well as its optical, geometric and/or solvate isomers, such as hydrates, or a composition containing it or them:

in which:
- AK1, AK2 and AK3 independently designate a monovalent hydrocarbon chain, linear or branched, saturated or unsaturated, in _C4 - _C30 , in particular in _C6 - _C24 , preferably in _C10 - _C24 , said chain being substituted by one or more ionic groups selected from -O- _PO3H2 , _-PO3H2 , O _{- SO3H} , _SO3H , _-COOH , N ⁺ ( _R1 )( _R2 )( _R3 ) ^An- , and being substituted by one or more identical or different radicals from -OR; said chain being optionally interrupted by one or more heteroatoms or groups selected from -O-, -S-, -C(O)-, epoxides, and their combinations such as -OC(O)- and -C(O)-O-;
- _R1 , _R2 and _R3 independently designate an alkyl radical, linear or branched in _C1 - _C20 , in particular in _C1 - _C12 , preferably in _C1 - _C6 , more preferably a methyl; _R1 , _R2 and _R3 are preferably saturated;
- An ^- designates a cosmetically acceptable anion, preferably chosen from among halides such as chlorides;
- R represents a hydrogen atom, a linear or branched alkyl radical, saturated or unsaturated in _C1 - _C6 , preferably in _C1 - _C4 , in particular a methyl, or a -C(O)-C(R _a )(R _b )-C(O)-R ₄ radical;
- R _a and R _b , identical or different, represent a hydrogen atom or a (C ₁ -C ₄ )alkyl group, preferably a hydrogen atom;
- R ₄ represents a monovalent hydrocarbon radical in C ₁ to C ₆ , linear or branched, saturated or unsaturated, preferably a (C ₁ -C ₄ )alkyl group, in particular methyl or tert-butyl, more preferably methyl;
it being understood that said compound of formula (I) contains at least two radicals -C(O)-C(R _a )(R _b )-C(O)-R ₄ ; and
ii) at least one crosslinking agent. A treatment process according to the preceding claim, wherein the compound(s) of formula (I), as well as their optical, geometric and/or solvate isomers, such as hydrates, are such that:
- AK1, AK2 and AK3 independently designate a branched monovalent hydrocarbon chain, saturated or unsaturated, in _C10 - _C24 , said chain being substituted by one or more ionic groups selected from -O- _PO3H2 , _-PO3H2 , _{O - SO3H} , _SO3H , -COOH, N ⁺ ( _R1 )( _R2 )( _R3 ) ^An- , and being substituted by one or more identical or different radicals from -OR; said chain being optionally interrupted by one or more heteroatoms or groups selected from -O-, -S-, -C(O)-, epoxides, and their combinations such as -OC(O)- and -C(O)-O-;
- R ₁ , R ₂ , R ₃ , R, R _a , R _b , An ^- and R ₄ are as defined in claim 1;
it being understood that said compound of formula (I) contains at least two radicals -C(O)-C(R _a )(R _b )-C(O)-R ₄ . A treatment process according to any one of the preceding claims, wherein the compound(s) of formula (I), as well as their optical, geometric and/or solvate isomers, such as hydrates, are such that:
- AK1, AK2 and AK3 independently designate a branched, unsaturated monovalent hydrocarbon chain, in _C10 - _C24 , said chain being substituted by one or more ionic groups selected from -O- _PO3H2 , _-PO3H2 , O- _SO3H , _SO3H and _-COOH , and being substituted by one or more identical or different radicals from -OR; said chain being optionally interrupted by one or more heteroatoms or groups selected from -O-, -S-, -C(O)-, epoxides, and their combinations such _as -OC(O)- and -C(O)-O-;
- R, _Ra , _Rb , and _R4 are as defined in claim 1;
it being understood that said compound of formula (I) contains at least two radicals -C(O)-C(R _a )(R _b )-C(O)-R ₄ . A treatment process according to any one of the preceding claims, wherein the compound(s) of formula (I), as well as their optical, geometric and/or solvate isomers, such as hydrates, are such that:
- AK1, AK2 and AK3 independently designate a branched and unsaturated monovalent hydrocarbon chain, in _C10 - _C24 , said chain being substituted by one or more ionic groups chosen from -O- _PO3H2 , _-PO3H2 , O- _SO3H , _SO3H , _-COOH , and being substituted by one or more identical or different _radicals from -OR;
- R, _Ra , _Rb , and _R4 are as defined in claim 1;
it being understood that said compound of formula (I) contains at least two radicals -C(O)-C(R _a )(R _b )-C(O)-R ₄ . A treatment process according to any one of the preceding claims, wherein the compound(s) of formula (I), as well as their optical, geometric and/or solvate isomers, such as hydrates, are such that:
- AK1, AK2 and AK3 independently designate a branched and unsaturated monovalent hydrocarbon chain, in _C10 - _C24 , said chain being substituted by one or more ionic groups chosen from -O- _PO3H2 , _-PO3H2 , O- _SO3H , _SO3H , _-COOH , and being substituted by one or more identical or different _radicals from -OR;
- R, _Ra , _Rb , and _R4 are as defined in claim 1;
it being understood that said compound of formula (I) contains at least two radicals -C(O)-C(R _a )(R _b )-C(O)-R ₄ . A treatment process according to any one of the preceding claims, wherein the compound(s) of formula (I), as well as their optical, geometric and/or solvate isomers, such as hydrates, are such that:
- AK1, AK2 and AK3 independently designate a branched and unsaturated monovalent hydrocarbon chain, in C ₁₀ -C ₂₄ , said chain being substituted by one or more ionic groups chosen from -O-PO ₃ H ₂ and O-SO ₃ H and being substituted by one or more identical or different radicals from -OR;
- R, _Ra and _Rb are as defined in claim 1;
- R ₄ represents a (C ₁ -C ₄ )alkyl group, in particular methyl;
it being understood that said compound of formula (I) contains at least two radicals -C(O)-C(R _a )(R _b )-C(O)-R ₄ . A treatment process according to claim 1, wherein the compound(s) of formula (I), as well as their optical, geometric and/or solvate isomers, such as hydrates, are such that:
- AK1, AK2 and AK3 independently designate a monovalent _, branched, unsaturated hydrocarbon chain, in _C4 - _C30 , said chain being substituted by one or more ionic groups chosen from -O- _PO3H2 , O- _SO3H , and being substituted by one or more identical or different radicals from -OR; said chain being optionally interrupted by one or more heteroatoms or groups chosen from -O-, -S-, -C(O)-, and their combinations such as -OC(O)- and -C(O)-O-;
- R, _Ra and _Rb are as defined in claim 1;
- R ₄ represents a (C ₁ -C ₄ )alkyl group, in particular methyl;
it being understood that said compound of formula (I) contains at least two radicals -C(O)-C(R _a )(R _b )-C(O)-R ₄ . A treatment process according to any one of the preceding claims, comprising the application to said keratin materials of at least ii) a crosslinking agent selected from (poly)amine, (poly)thiol, metal alkoxide compounds and mixtures thereof, preferably selected from (poly)amine, (poly)thiol compounds and mixtures thereof, and more preferably selected from (poly)amine compounds. A treatment method according to any one of the preceding claims, comprising applying to said keratinous materials at least ii) a crosslinking agent selected from:
A) (Poly)amine compounds selected from:
ia) chitosans such as poly(D-Glucosamine),
ib) diamine polyethers, in particular α,ω-diamine polyethylene glycols, with an amine function at the end of the chain,
ic) triamine polyethers, in particular polyetheramine (or jeffamine),
id) aminoalkoxysilanes, in particular APTES,
ie) the polyamine compounds NH2 _- alk- _NH2 , in which alk denotes a divalent hydrocarbon chain in _C2 - _C20 , possibly interrupted by one or more heteroatoms selected from -O-, -N(R)- with R denoting a hydrogen atom or a _C1 - _C4 alkyl radical, in particular spermidine and 4,7,10-Trioxa-1,13-tridecanediamine, and
if) polydialkylsiloxanes comprising primary amine groups at the end of the chain or on side chains, in particular polydimethylsiloxanes comprising primary amine groups, more particularly poly(dimethoxysiloxane) terminated by bis(3-aminopropyl) (PDMS-diNH ₂ ) and amodimethicones comprising amine groups on side chains, more particularly bis-cetearyl amodimethicone;
B) (poly)thiol compounds selected from:
iia) thiol-group polydialkylsiloxanes, and
iib) alkoxysilanes with thiol functions,
and in particular selected from compounds iia) polydialkylsiloxanes with thiol functions, preferably from polydimethylsiloxanes comprising thiol groups on the side chain, in particular mercaptopropyl, and more particularly selected from compounds of formula (XII):
R ^a -Si(R ^b )(R ^d )-O-[Si(R ^a )(R ^b )-O] _m -[Si(R ^b )(ALK ₁ -SH)-O] _n -Si(R ^b )(R ^d )-R ^a (XII)
formula (XII) in which:
- R ^a and R ^b , identical or different, preferably identical, represent a (C ₁ -C ₄ )alkyl group, in particular methyl, an (C ₁ -C ₄ )alkoxy group, in particular methoxy, an aryl group, in particular phenyl, an aryloxy group, in particular phenoxy, an aryl(C ₁ -C ₄ )alkyl group, in particular benzyl, or an aryl(C ₁ -C ₄ )alkoxy group, in particular benzoxy, and preferably a (C ₁ -C ₄ )alkyl group, more preferably methyl,
- R ^d represents a ( _C1 - _C4 )alkyl group, in particular methyl, an ( _C1 - _C4 )alkoxy group, in particular methoxy, an aryl group, in particular phenyl, an aryloxy group, in particular phenoxy, an aryl( _C1 - _C4 )alkyl group, in particular benzyl, an aryl( _C1 - _C4 )alkoxy group, in particular benzoxy, or a ( _C1 - _C6 )alkyl group substituted by a ( _C1 - _C4 )alkylamino, amino, or thiol group, and preferably a ( _C1 - _C4 )alkyl group, more preferably methyl,
and preferably R ^a , R ^b , and R ^d , are identical and represent a (C ₁ -C ₆ )alkyl group, more preferably methyl,
- ALK ₁ represents a divalent hydrocarbon chain comprising from 1 to 100 carbon atoms, saturated or unsaturated, linear or branched, possibly cyclic, possibly interrupted by one or more heteroatoms, such as oxygen, sulfur or nitrogen, in particular oxygen, a (thio)carbonyl group C(X) with X representing O or S, or their combinations, in particular -O-, -OC(O)- or -C(O)-O-, preferably ALK ₁ represents a (C ₁ -C ₆ )alkylene group, more preferably (C ₁ -C ₄ )alkylene, even more preferably propylene,
- n and m, whether identical or different, represent an integer greater than 2, and in particular the values of m and n are such that the average molecular weight by weight of said polyorganosiloxane is between 1000 and 55,000 g.mol ^-1 ; and
C) Metal alkoxides selected from: zirconium ethoxide (Zr( _OC₂H₅ ) _₄ ), zirconium propoxide (Zr( _{OCH₂CH₂CH₃} ) _₄ ), zirconium isopropoxide (Zr( _OCH ( _CH₃ ) _₂ ) _{₄ )} , zirconium butoxide (Zr( _{OCH₂CH₂CH₂CH₃ ) ₄} ), zirconium tert-butoxide (Zr(OC( _CH₃ ) _₃ ) _{₄ )} , titanium ethoxide (Ti( _OC₂H₅ ) _₄ ), titanium propoxide (Ti( _{OCH₂CH₂CH₃} ) _₄ ), titanium isopropoxide (Ti( _OCH ( _CH₃ ) _{₂ )₄ ) , titanium} butoxide ( _{Ti ( OCH₂CH₂CH₂CH₃ ) ₄ )} ), _titanium tert-butoxide (Ti(OC(CH3) ₃ ) _{4 )} , titanium ₂ -ethylhexyloxide (Ti(OCH2CH( _C2H5 )( _CH2 ) _3CH3 ) _{4 )} , and mixtures thereof, more preferably chosen from zirconium propoxide, titanium propoxide, titanium butoxide and mixtures thereof. A treatment method according to any one of the preceding claims, wherein iii) at least one cosmetic active ingredient is further applied to keratinous materials, in particular skin, lips, eyelashes and/or eyebrows and/or keratinous fibers, in particular hair, preferably the cosmetic agent(s) iii) being selected from:
a) coloring materials, in particular selected from pigments, direct colorants and mixtures thereof,
b) active ingredients for the care of keratin fibers, preferably hair fibers,
c) UV filters, and
d) their mixtures;
preferably the cosmetic agent(s) iii) are chosen from a) coloring materials, preferably chosen from pigments, direct colorants and their mixtures, more preferably the pigment(s) are chosen from carbon black, iron oxides, in particular yellow, red and black and iron oxide coated micas, triarylmethane pigments, in particular blue and violet, in particular BLUE 1 LAKE, azo pigments, in particular red, more particularly D&C RED 7, the alkali metal salt of lithol red, in particular the calcium salt of lithol red B, and
even more preferentially among red iron oxides, yellow iron oxides and azo pigments, especially red ones, more particularly D&C RED 7. A treatment method according to any one of the preceding claims, wherein the following is further implemented: (iv) at least one fat, in particular at least one oil, preferably at least one volatile oil, more preferably at least one oil selected from:
- hydrocarbon oils having 8 to 16 carbon atoms, in particular _C8 - _C16 branched alkanes, in particular isoalkanes, more particularly isoalkanes (also called isoparaffins), preferably _C13 - _C16 isoparaffin, isododecane, isodecane, isohexadecane, for example oils sold under the trade names Isopars or Permetyls, alone or in mixtures, preferably isododecane (also called 2,2,4,4,6-pentamethylheptane), linear alkanes, in particular _C11 - _C16 , alone or in mixtures, in particular hexane, decane, undecane, tridecane, isoparaffins in particular n-dodecane ( _C12 ) and n-tetradecane ( _C14 ), the undecane-tridecane mixture, the mixtures of n-undecane (C ₁₁ ) and n-tridecane (C ₁₃ ), and their mixtures as well as the mixtures of n -undecane (C ₁₁ ) and n -tridecane (C ₁₃ ), and the non-aromatic, volatile C ₅ -C ₁₂ cyclic alkanes;
- short-chain esters having a total of 3 to 8 carbon atoms, in particular ethyl acetate, methyl acetate, propyl acetate, n-butyl acetate;
- hydrocarbon carbonate oils of structure R' ₁ -OC(O)-O-R' ₂ in which R' ₁ and R' ₂ independently designate a linear, branched or cyclic C ₄ -C ₈ alkyl group, preferably a C ₄ -C ₈ alkyl group, advantageously, more preferably chosen from dibutyl carbonate or dipentyl carbonate;
- ether oils of formula R ₁ -OR ₂ , in which R ₁ and R ₂ designate, independently of each other, a linear, branched or cyclic C ₄ -C ₈ alkyl group, preferably a C ₄ -C ₈ alkyl group;
- silicone oils, in particular comprising 2 to 7 silicon atoms, and possibly comprising alkyl or alkoxy groups having 1 to 10 carbon atoms, in particular dimethicones of viscosity 5 and 6 cSt, cyclopentadimethylsiloxane, dodecamethylpentasiloxane, cyclohexadimethylsiloxane, octamethyl cyclotetrasiloxane, decamethyl cyclopentasiloxane, dodecamethyl cyclohexasiloxane, heptamethyl hexyltrisiloxane, heptamethyloctyl trisiloxane, hexamethyl disiloxane, octamethyl trisiloxane, decamethyl tetrasiloxane, dodecamethyl pentasiloxane, and mixtures thereof;
more preferably the volatile oil(s) iv) are chosen from among the _C8 - _C16 alkanes, in particular branched, preferably isododecane. Processing method according to any one of the preceding claims, wherein at least one water-soluble solvent is further used, in particular selected from lower monoalcohols having 1 to 6 carbon atoms, in particular from ethanol and isopropanol, preferably ethanol. Process for treating, in particular for cosmetic purposes, keratinous materials, especially for the care and/or makeup of the skin, lips, eyelashes and/or eyebrows and/or for the care, styling and/or coloring of keratinous fibers, preferably hair, comprising the application to said keratinous materials of at least:
- a composition, referred to as "C1", comprising i) at least one compound of formula (I) as defined in claims 1 to 7, and optionally iii) at least one cosmetic active ingredient, in particular as defined in claim 10; preferably, composition "C1" does not comprise ii) a crosslinking agent;
- a composition, referred to as "C2", comprising i) at least one compound of formula (I), as defined in claims 1 to 7, ii) at least one crosslinking agent, in particular as defined in claims 8 to 9, and optionally iii) at least one cosmetic active ingredient, in particular as defined in claim 10; preferably, composition "C2" does not comprise iii) a cosmetic active ingredient;
- a composition, referred to as "C3", comprising i) at least one compound of formula (I), as defined in claims 1 to 7, ii) at least one crosslinking agent, in particular as defined in claims 8 to 9, and iii) at least one cosmetic active ingredient, in particular as defined in claim 10;
- a composition, referred to as "C4", comprising ii) at least one crosslinking agent, in particular as defined in claims 8 to 9, and optionally iii) at least one cosmetic active ingredient, in particular as defined in claim 10; preferably, composition "C4" does not comprise i) at least one compound of formula (I) as defined in claims 1 to 7; and/or
- a composition, referred to as "C5", comprising iii) at least one cosmetic active ingredient, in particular as defined in claim 10; preferably, composition "C5" does not comprise i) at least one compound of formula (I) as defined in claims 1 to 7, and does not comprise ii) at least one crosslinking agent;
provided that the process employs i) at least one compound of formula (I) as defined in claims 1 to 7, and ii) at least one crosslinking agent, and that the compositions "C1", "C2", "C3", "C4" and "C5" may be anhydrous, aqueous such as hydroalcoholic and/or comprise one or more fatty substances iv), in particular as defined in claim 11. Treatment method according to the preceding claim, characterized in that it comprises either a single step of applying composition "C2" or composition "C3" to said keratinous materials; or two successive steps of applying to said keratinous materials, two different compositions, preferably composition "C1" and then composition "C4". A cosmetic treatment process for the care and/or makeup of keratinous materials, particularly of the skin, lips, eyelashes and/or eyebrows, and/or for the care, styling and/or coloring of keratinous fibers, preferably hair, comprising the successive application to said keratinous materials of at least:
- i) at least one compound of formula (I) as defined in claims 1 to 7, or of a composition referred to as "C1" containing it or them and optionally comprising iii) at least one cosmetic active ingredient, in particular as defined in claim 10; then
- a composition, referred to as "C4", comprising ii) at least one crosslinking agent, in particular as defined in claims 8 to 9, and optionally iii) at least one cosmetic active ingredient, in particular as defined in claim 10;
at least one of the compositions "C1" and/or "C4" containing at least one colouring material, in particular as defined above and below, preferably at least one pigment, and more preferably composition "C1" includes at least one pigment. Compound of formula (I)

in which:
- AK1, AK2 and AK3 independently designate a monovalent hydrocarbon chain, linear or branched, saturated or unsaturated, in _C4 - _C30 , in particular in _C6 - _C24 , preferably in _C10 - _C24 , said chain being substituted by one or more ionic groups selected from -O- _PO3H2 , _-PO3H2 , O _{- SO3H} , _SO3H , _-COOH , N ⁺ ( _R1 )( _R2 )( _R3 ) ^An- , and being substituted by one or more identical or different radicals from -OR; said chain being optionally interrupted by one or more heteroatoms or groups selected from -O-, -S-, -C(O)-, epoxides, and their combinations such as -OC(O)- and -C(O)-O-;
- _R1 , _R2 and _R3 independently designate an alkyl radical, linear or branched in _C1 - _C20 , in particular in _C1 - _C12 , preferably in _C1 - _C6 , more preferably a methyl; _R1 , _R2 and _R3 are preferably saturated;
- An ^- designates a cosmetically acceptable anion, preferably chosen from among halides such as chlorides;
- R represents a hydrogen atom, a linear or branched alkyl radical, saturated or unsaturated in _C1 - _C6 , preferably in _C1 - _C4 , in particular a methyl, or a -C(O)-C(R _a )(R _b )-C(O)-R ₄ radical;
- R _a and R _b , identical or different, represent a hydrogen atom or a (C ₁ -C ₄ )alkyl group, preferably a hydrogen atom;
- R ₄ represents a monovalent hydrocarbon radical in C ₁ to C ₆ , linear or branched, saturated or unsaturated, preferably a (C ₁ -C ₄ )alkyl group, in particular methyl or tert-butyl, more preferably methyl;
it being understood that said compound of formula (I) contains at least two radicals -C(O)-C(R _a )(R _b )-C(O)-R ₄ ,
as well as its salts, isomers and/or solvates such as hydrates. A process for preparing compounds of formula (I) according to the preceding claim, comprising at least one reaction step of a compound of formula (II):

in which,
- AK'1, AK'2 and AK'3 independently designate a linear or branched monovalent hydrocarbon chain, saturated or unsaturated, in _C4 - _C30 , in particular in _C6 - _C24 , preferably in _C10 - _C24 , said chain being substituted by one or more ionic groups selected from -O- _PO3H2 , _-PO3H2 , O _{- SO3H} , _SO3H - _COOH , N ⁺ ( _R1 )( _R2 )( _R3 ) ^An- , and being substituted by one or more identical or different radicals from -OH; said chain being optionally interrupted by one or more heteroatoms or groups selected from -O-, -S-, -C(O)-, epoxides, and their combinations such as -OC(O)- and -C(O)-O-, in particular -S-;
- _R1 , _R2 and _R3 independently designate an alkyl radical, linear or branched in _C1 - _C20 , in particular in _C1 - _C12 , preferably in _C1 - _C6 , more preferably a methyl; _R1 , _R2 and _R3 are preferably saturated;
- An ^- designates a cosmetically acceptable anion, preferably chosen from among halides such as chlorides;
provided that said compound of formula (II) contains a) at least one ethylenic unsaturation or b) at least two hydroxy radicals or c) at least one hydroxy radical and at least one ethylenic unsaturation. Composition, preferably cosmetic, containing at least one compound selected from the compounds of formulas (I) according to any one of claims 1 to 7, as well as their salts, isomers and/or solvates such as hydrates. Cosmetic use of a composition referred to as "C3", for the treatment of keratinous materials, in particular of the skin, lips, eyelashes and/or eyebrows and/or for the care, styling and/or coloring of keratinous fibers, preferably of hair, comprising i) at least one compound of formula (I) according to any one of claims 1 to 7, ii) at least one crosslinking agent, in particular according to claims 8 and 9, and iii) at least one cosmetic active, in particular according to claim 10. A kit or device, particularly a cosmetic one, with multiple compartments comprising:
- at least one compartment containing i) at least one compound of formula (I) according to any one of claims 1 to 7, and optionally iii) at least one cosmetic active ingredient, in particular according to claim 10, in particular comprising composition "C1" according to claim 13;
- at least one compartment separate from that which contains i) and ii) at least one crosslinking agent, in particular according to claims 8 and 9, and optionally iii) at least one cosmetic active ingredient, in particular according to claim 10, in particular comprising composition "C4" according to claim 13; and
- optionally, at least one compartment separate from those containing i) and ii), and containing iii) at least one cosmetic active ingredient, in particular according to claim 10, identical or different from that/those possibly contained in the compartments comprising i) and ii).