FR2954132A1 - Composition, useful for make-up and/or care of keratin materials, preferably lips and as e.g. sunscreen or tanning agent, comprises supramolecular compound and at least polar pasty fatty substances in a medium - Google Patents

Abstract

Cosmetic composition (A) comprises: in a medium, (a) a supramolecular compound (Q); and (b) at least polar pasty fatty substances, where (Q) is obtained by reacting: at least one oil having at least one reactive nucleophile group comprising hydroxyl or amine groups, and at least one linking group capable of establishing hydrogen bonds with one or more linking groups, which further comprises at least one pyrimidin-4-one unit (I) or (II). Cosmetic composition (A) comprises: in a medium, (a) a supramolecular compound (Q); and (b) at least polar pasty fatty substances, where (Q) is obtained by reacting: at least one oil having at least one reactive nucleophile group comprising hydroxyl (OH) or amine groups (NH 2), and at least one linking group capable of establishing hydrogen bonds with one or more linking groups, each pairing of a linking group involving at least three hydrogen bonds, where the linking group comprises at least one reactive isocyanate and imidazole function, which may react with the reactive functional group carried by the oil, and the linking group further comprising at least one pyrimidin-4-one unit of formula (I) or (II). R1, R3 : divalent carbon radical comprising (i) linear or branched 1-32C alkyl, (ii) 4-16C cycloalkyl and (iii) 4-16C aryl, optionally including 1-8 heteroatoms of O, N, S, F, Si or P, and/or optionally substituted by an ester, amide and/or 1-12C alkyl; and R2 : H or carbon radical, including linear, branched or cyclic, optionally saturated, optionally aromatic 1-32C hydrocarbon (optionally including one or more heteroatoms of O, N, S, F, Si or P). [Image].

Description

The present invention relates to a cosmetic composition, especially for the care and / or makeup of keratinous substances, in particular the skin or the lips, comprising new compounds A (called, in the context of this application, supramolecular compounds) capable of establishing hydrogen bonds with partner junction groups, associated with a pasty polar fatty substance.

There are many cosmetic compositions for which gloss properties of the deposited film, after application to keratin materials, are desired. Examples include lipsticks or nail polish. In order to obtain such a result, it is possible to associate particular raw materials, in particular lanolins, with so-called brilliant oils such as polybutenes, or acid or fatty alcohol esters whose number of carbon is high; or some vegetable oils; or else esters resulting from the partial or total esterification of an aliphatic compound hydroxylated with an aromatic acid, as described in Patent Application EP1097699, or else pasty fatty substances.

However, these pasty fatty substances associated with compounds obtained by modifying oils with OH or NH 2 function, can cause a sticky problem. This sticky nature leads these formulas to leave traces on the supports such as glasses, coffee cups.

The formulator is therefore in search of raw materials and / or systems making it possible to obtain homogeneous compositions whose deposit is characterized by a non-transfer and non-sticking effect, and preferably by brightness and comfort.

The object of the present invention is to provide cosmetic compositions which make it possible to obtain such a uniform deposit on keratin materials, said deposit combining good non-transfer properties, while being non-tacky, and preferably shiny and comfortable to wear.

The subject of the present invention is therefore a cosmetic composition for makeup and / or care of keratinous substances (in particular of the skin or the lips) comprising, in a cosmetically acceptable medium, (i) a compound A (called, in the context of this application, a supramolecular compound) obtainable by reaction between: at least one oil carrying at least one nucleophilic reactive functional group chosen from OH and NH 2, and at least one linking group capable of establishing hydrogen bonds with a or more than one joining group, each pairing of a linking group involving at least 3 hydrogen bonds, said linking group carrying at least one isocyanate or imidazole reactive functional group capable of reacting with the reactive function carried by the oil, said joining group further comprising at least one unit of formula (I) or (II): ## STR5 ## wherein R 2 is selected from the group consisting of: ## STR1 ## HII o (I) (II) in which: R1 and R3, which are identical or different, represent a divalent carbon radical chosen from (i) a linear or branched C1-C32 alkyl group, (ii) a C4 cycloalkyl group; C16 and (iii) a C4-C16 aryl group; optionally comprising 1 to 8 heteroatoms selected from O, N, S, F, Si and P; and / or optionally substituted with an ester, amide or a C1-C12 alkyl radical; or a mixture of these groups; R2 represents a hydrogen atom or a linear, branched or cyclic, saturated or unsaturated, optionally aromatic, hydrocarbon radical, in C1-C32, which may comprise one or more heteroatoms chosen from O, N, S, F, Si and P; (ii) at least one pasty, polar fatty substance.

Supramolecular compounds: The compounds A (also called supramolecular compounds) functionalized according to the present invention are in the form of a solid; this allows in particular to form a non-sticky material, which does not transfer to the finger when applied to the keratin materials; this is not the case with the functionalized compounds of the prior art, especially as described in US Pat. No. 5,70,712, which are in the form of a liquid, more or less viscous, and which form a tacky material which transfers finger after application on keratin materials. Furthermore, it has been found that the crosslinking through four hydrogen bonds, via the ureidopyrimidone groups, could make it possible to increase the strength of this crosslinking, and thus improve the holding of the desired cosmetic effect, in particular the holding deposition or gloss. In addition, the compounds or functionalized oils according to the invention are easily transportable in the usual cosmetic media, especially the usual cosmetic oily media.

They are advantageously compatible with the oils usually present in cosmetic compositions, and also have good properties for dispersing pigments or fillers.

They are easily transportable in solvent or oily cosmetic media, in particular oils, fatty alcohols and / or fatty esters, which facilitates their use in the cosmetic field, especially in lipsticks. They have a suitable solubility in various cosmetic oily media, such as vegetable oils, alkanes, short butyl acetate esters or ethyl, or fatty, fatty alcohols and especially in environments comprising isododecane, Parleam, isononyl isononanoate, octyldodecanol, and / or a C12-C15 alkyl benzoate.

The cosmetic compositions according to the invention also have good applicability and good coverage; good adhesion to the support, whether on the nail, eyelashes, skin or lips; adequate flexibility and film strength, as well as an excellent level of lasting gloss. The comfort and slip properties are also very satisfying. In general, in the context of the present application, the compounds A may be referred to as "supramolecular compounds" for convenience and for clarity.

The compounds A (or so-called supramolecular) compounds of the invention are obtainable by reaction between: - at least one oil carrying at least one nucleophilic reactive function selected from OH and NH2, and - at least one joining group capable of establishing hydrogen bonds with one or more partner joining groups, each pairing of a linking group involving at least 3 hydrogen bonds, said linking group carrying at least one isocyanate or imidazole reactive functional group capable of reacting with the reactive function carried by the oil, said joining group further comprising at least one unit of formula (I) or (II): ## STR1 ## (I) (II) in which: R1 and R3, which may be identical or different, represent a divalent carbon radical chosen from (i) a linear or branched C1-C32 alkyl group, (ii) a C4-C16 cycloalkyl group and (iii) a C4-C16 aryl group; optionally comprising 1 to 8 heteroatoms selected from O, N, S, F, Si and P; and / or optionally substituted with an ester, amide or a C 1 -C 12 alkyl radical; or a mixture of these groups; R2 represents a hydrogen atom or a linear, branched or cyclic, saturated or unsaturated, optionally aromatic, hydrocarbon radical, in C1-C32, which may comprise one or more heteroatoms chosen from O, N, S, F, Si and P.

In the end, the supramolecular compounds of the compositions according to the invention therefore comprise at least one part (HB) originating from the oil and at least one part (G) originating from the joining group, said part (G) comprising at least one unit of formula (I) or (II). In particular, said parts (HB) and (G) are connected by a covalent bond, in particular can be connected by a covalent bond formed during the reaction between the OH and / or NH 2 reactive functional groups carried by the oil and the isocyanate functions carried. by the joining group; or between the reactive functions NH2 carried by the oil and the isocyanate or imidazole functions carried by the linking group.

It is thus possible, in particular, to schematize the preferential obtaining of the compounds according to the invention by the chemical reaction between the following entities: (HB) - (OH) m (NH 2) n + (G) - (NCO) p or else (HB) - (OH) m (NH 2) n + (G) - (imidazole) p with m, n and p being non-zero integers.

The oil that can be used to prepare the supramolecular compound according to the invention, which can preferably be schematized (HB) - (OH) m (NH 2) n, is a non-crystalline fatty substance or a mixture of fatty substances. at 25 ° C, liquid at room temperature and at atmospheric pressure (25 ° C, 1 atm.); preferably apolar, or preferably preferably not soluble in water.

Preferably, the oil that can be used to prepare the supra-molecular compound according to the invention is non-polymeric.

By liquid is meant that the viscosity of the compound is less than or equal to 2500 centipoise, at 110 ° C., 1 atm., Measured with a Brookfield DV-1 or Brookfield Cap 1000+ rheometer, the person skilled in the art choosing apparatus suitable for measuring viscosity.

By apolar is meant a compound whose HLB (hydrophilic lipophilic balance) value is low; in particular less than or equal to 8, preferably less than or equal to 4, and more preferably less than or equal to 2; preferentially, the value of HLB must be sufficiently low to make it possible to obtain a supramolecular material which is not, or not too much, hygroscopic.

By non-soluble it is meant that the fraction of oil which can dissolve in water, at 25 ° C., 1 atm., Is less than 5% by weight (ie 5 g of oil in 100 ml of water ); preferably less than 3%. By fatty substance is meant in particular but not exclusively, a hydrocarbon compound comprising one or more alkyl chains, linear, cyclic, branched, saturated or unsaturated, having at least 6 carbon atoms and may comprise polar groups such as an acid group, a hydroxyl or polyol, amine, amide, phosphoric acid, phosphate, ester, ether, urea, carbamate, thiol, thioether, thioester, this chain may contain up to 100 carbon atoms.

Preferably, the oil which can be used to prepare the supramolecular compound according to the invention is a glossy oil, that is to say having a refractive index greater than or equal to 1.46 at 25.degree. , in particular between 1.46 and 1.55 (the refraction index being defined with respect to the D line of sodium, at 25 ° C.).

Preferably, the oil which can be used to prepare the supramolecular compound according to the invention is a non-volatile oil. The term "non-volatile oil" means an oil which may remain on the keratin materials at ambient temperature and atmospheric pressure for at least several hours, and in particular having a vapor pressure of less than 10 -3 mm Hg (0.13 Pa). ). Preferably, the oil has a molar mass (Mw) of between 150 and 6000, especially between 170 and 4000, or even between 180 and 2000, preferably between 200 and 1500, and more preferably between 220 and 800 g / mol.

The oil which can be used in the context of the present invention to prepare the supramolecular compound carries at least one reactive functional group capable of reacting with the reactive function carried on the linking group, in particular capable of reacting chemically with the groups isocyanates or imidazole carried by the joining group; preferably, this function is an OH or NH 2 function. Preferably, the oil comprises only OH functions, in particular 1 to 3 OH functions, preferably primary or secondary OH functions, and still better only primary.

The oil according to the present invention is preferably a carbonaceous oil, in particular a hydrocarbon oil, which, in addition to the reactive functional group capable of reacting with the linking group, may comprise oxygen, nitrogen, sulfur and / or phosphorus. The oil is very preferably selected from cosmetically acceptable oils.

The oil that can be used in the context of the present invention to prepare the supramolecular compound may be chosen from:

(i) fatty alcohols, comprising 6 to 50 carbon atoms, linear, branched or cyclic, saturated or unsaturated, comprising 1 or more OH; optionally comprising one or more NH 2. Mention may in particular be made of: linear or branched C 6 -C 50, especially C 6 -C 32, in particular C 8 -C 28, saturated or unsaturated monoalcohols, and in particular isostearyl alcohol, cetyl alcohol and oleic alcohol; , oleyl alcohol, isopalmitoyl alcohol, butyl-2-octanol, hexyl-2-decane, 2-octyl decanol, 2-octyldodecanol, 2-octyltetradecanol, decylbenzoyl, 2 tetradecanol, 2-dodecyl hexadecanol, and especially the alcohols sold under the name Jarcol by Jarchem Industries, such as Jarcol 1-12, Jarcol 1-16, Jarcol 1-20 and Jarcol 1-24; linear or branched C 6 -C 50, especially C 6 -C 40, especially C 8 -C 38, saturated or unsaturated diols, and in particular C 32 -C 36 branched diols, and in particular the Uniqema Pripol 2033 commercial product; linear or branched triols of C 6 -C 50, especially C 6 -C 32, in particular C 8 -C 28, saturated or unsaturated, and especially phytantriol; (ii) esters and ethers bearing at least one free OH group, and in particular esters and partial polyol ethers, and hydroxylated carboxylic acid esters.

By partial polyol ester is meant the esters prepared by esterification of a polyol with a carboxylic acid, substituted or unsubstituted, the reaction not being total, that is to say not carried out on all the free OH of the polyol; in the end, the ester therefore still has at least one free OH. Preferably, the carboxylic acid is a monoacid. It is also possible to use a mixture of carboxylic acids, in particular monocarboxylic acids.

Partial polyol ether is understood to mean the ethers prepared by etherification of a polyol, on itself or with at least one other alcohol, mono or polyhydroxylated, preferably monoalcohol, the etherification reaction not being complete, c that is, not performed on all the free OHs of the polyol; in the end, the ether still has at least one free OH.

By hydroxyl carboxylic acid ester is meant the esters (mono and poly) prepared by reaction between a carboxylic acid carrying at least one OH function, and one or more alcohols (mono or poly), preferably monoalcohol, the reaction. may be total or partial (performed on all or part of the free OH of the alcohol).

Among the polyols that may be used to prepare the above esters or ethers, mention may be made of propylene glycol, glycerol, neopentyl glycol, trimethylolpropane, trimethylolethane, polyglycerols and especially polyglycerol-2, polyglycerol-3 and polyglycerol. -10; erythritol, dipentaerythritol, pentaerythritol, di-trimethylolpropane, phytantriol, sucrose, glucose, methylglucose, sorbitol, fructose, xylose, mannitol, glucosamine; as well as diol dimers in particular obtained from dimeric fatty acids, especially C32-C38 branched diols, especially C36, aliphatic and / or alycyclic diols, such as those defined in the Hofer et al. European Coating Journal (March 2000), pages 26-37; and their mixtures.

Among the monoalcohols that can be used to prepare the above esters or ethers, mention may be made of linear or branched, preferably branched, C 3 -C 50 alcohols, and especially 2-ethylhexanol, octanol, alcohol and the like. isostearyl, and mixtures thereof.

Among the carboxylic acids which may be used to prepare the above esters or ethers, mention may be made of monoacids having 6 to 50 carbon atoms and diacids having 3 to 12 carbon atoms, linear or branched, saturated or unsaturated, among which may be mentioned octyldodecyl acid, hexyldecyl acid, ethylhexylic acid, isostearic acid, nonanoic acid, isononanoic acid, arachidic acid, stearic acid, palmitic acid, oleic acid, oxalic acid, adipic acid, succinic acid, fumaric acid, maleic acid, capric acid, hexanedioic acid, decyl acid, acid decanoic, and their mixtures.

Among the hydroxylated carboxylic acids that may be used to prepare the above esters or ethers, mention may be made of monohydroxylated or polyhydroxylated, preferably monohydroxylated acids; having 4 to 28 carbon atoms for example, and in particular 12-hydroxystearic acid, ricinoleic acid, malic acid, lactic acid, citric acid; and their mixtures.

Thus, the oil which may be used to prepare the supramolecular compound in the present invention may be chosen from, alone or as a mixture: the partial esters of pentaerythritol, and in particular pentaerythrityl adipate, pentaerythrityl caprate, pentaerythrityl succinate, pentaerythrityl tetraisonanoate, pentaerythrityl triisononanoate, pentaerythrityl tetraisostearate, pentaerythrityl triisostearate, pentaerythrityl tetradecyltetradecanoate, pentaerythrityl tetraethyl hexanoate, pentaerythrityl tetraoctyl dodecanoate. dipentaerythritol diesters, triesters, tetraesters or pentaesters, and especially dipentaerythrityl pentaisononanoate, dipentaerythrityl pentaisostearate, dipentaerythrityl tetraisostearate, di pentaerythrityl tri (polyhydroxystearate); trimethylolpropane mono- and di-esters, such as trimethylolpropane monoisostearate, trimethylolpropane diisostearate, trimethylolpropane monoethyl-2-hexylate and trimethylolpropane diethyl-2-hexylate; mono-, di- and tri-esters of di-trimethylolpropane such as di-trimethylolpropane diisostearate, di-trimethylolpropane triisostearate, di-trimethylolpropane tri-ethyl hexanoate; the mono-esters or partial polyesters of glycerol or polyglycerols, and especially: glycerol di-isostearate, glycerol di-isononanoate, polyglycerol-2 mono-, di- and tri-esters; for example with isostearic acid, 2-ethyl hexyl acid and / or isononanoic acid; and in particular polyglyceryl-2-isostearate; polyglyceryl-2-diisostearate; polyglyceryl-2 triisostearate; polyglyceryl-2-nonaisostearate; polyglyceryl-2-nonanoate; mono-, di-, tri- or tetra-esters of polyglycerol-3; for example with either isostearic acid, 2-ethyl hexyl acid and / or isononanoic acid; and especially polyglyceryl-3-isostearate, polyglyceryl-3-diisostearate; polyglyceryl-3 triisostearate; polyglyceryl-3-nonaisostearate; polyglyceryl-3-nonanoate; partial esters of polyglycerol-10 and in particular polyglyceryl-10 nonaisostearate; polyglyceryl-10-nonanoate; polyglyceryl-10-isostearate, polyglyceryl-10-diisostearate, polyglyceryl-10 triisostearate; propylene glycol monoesters such as propylene glycol monoisostearate, propylene glycol neopentanoate, propylene glycol monooctanoate; dimer-diol monoesters such as isostearyl dimer dilinoleate and octyl dodecyl dimer dilinoleate; glycerol ethers, such as polyglyceryl-2-oleyl ether, polyglyceryl-3-cetyl ether, polyglyceryl-3-decyltetradecyl ether and polyglyceryl-2 stearyl; esters between hydroxylated mono-, di- or tri-carboxylic acid and monoalcohols, and in particular: esters, in particular monoesters, of 12-hydroxystearic acid; such as octyl hydroxystearate and octyl-2-dodecyl hydroxystearate; mention may also be made of the corresponding oligomeric polyhydroxystearates, in particular having a degree of polymerization of 1 to 10, having at least one residual OH; esters of lactic acid, and in particular C4-40 alkyl lactates, such as 2-ethylhexyl lactate, diisostearyl lactate, isostearyl lactate, isononyl lactate, lactate, 2-octyldodecyl; malic acid esters, and in particular C4-40 alkyl malates, such as 2-diethyl hexyl malate, diisostearyl malate, 2-dioctyl dodecyl malate; esters of citric acid, and in particular C4-40 alkyl citrates, such as triisostearyl citrate, triisocetyl citrate and tri-isoarachidyl citrate.

(iii) natural, modified natural oils, vegetable, hydroxylated and in particular: - triglycerine esters carrying one or more OH, - castor oil, hydrogenated or not, and its derivatives in particular from the transesterification of the oil castor oil; like the Polycin M-365 or Polycin 2525 products sold by Vertellus; modified epoxidized oils, the modification consisting of opening the epoxy function to obtain a diol, and especially hydroxylated modified soybean oil; hydroxylated soybean oils (directly hydroxylated or first epoxidized); and in particular Agrol 2.0, Agrol 3.0 or Agrol 7.0 oils marketed by BioBased Technologies, LLC; Soyol oil R2-052 from Urethane Soy System; Renuva oils marketed by Dow Chemical; BioH Polyol 210 and 500 oils marketed by Cargill.

According to a first particularly preferred embodiment, the oil that can be used to prepare the supramolecular compound in the context of the present invention is chosen from fatty alcohols comprising 6 to 50 carbon atoms, linear, branched or cyclic, saturated or unsaturated, comprising 1 or more OH; optionally comprising one or more NH 2, such as: linear or branched C 6 -C 50, especially C 6 -C 32, in particular C 8 -C 28, saturated or unsaturated monoalcohols, and in particular isostearyl alcohol, alcohol Cetyl alcohol, oleic alcohol, oleyl alcohol, isopalmitoyl alcohol, 2-butyl octanol, 2-hexyl decanol, 2-octyl decanol, 2-octyl dodecanol, 2-octyltetradecanol 2-decetetradecanol, 2-dodecyl hexadecanol, and especially the alcohols sold under the name Jarcol by Jarchem Industries, such as Jarcol 1-12, Jarcol 1-16, Jarcol 1-20 and Jarcol. 1-24; linear or branched C 6 -C 50, especially C 6 -C 40, especially C 8 -C 38, saturated or unsaturated diols, and in particular C 32 -C 36 branched diols, and in particular the Uniqema Pripol 2033 commercial product; linear or branched triols of C 6 -C 50, especially C 6 -C 32, in particular C 8 -C 28, saturated or unsaturated, and especially phytantriol;

According to this first preferred embodiment, the oil that can be used to prepare the supramolecular compound in the context of the present invention is preferably chosen from linear or branched C 6 -C 50, especially C 6 -C 32, monohydric alcohols. , in particular C8-C28, saturated or unsaturated, and in particular isostearyl alcohol, cetyl alcohol, oleic alcohol, oleyl alcohol, isopalmitoyl alcohol, butyl-2-octanol, hexyl-2 decanol, 2-octyl decanol, 2-octyldodecanol, 2-octyltetradecanol, 2-decyltetradecanol, 2-dodecyl hexadecanol, and especially the alcohols sold under the name Jarcol by the company Jarchem Industries, such as Jarcol 1-12, Jarcol I-16, Jarcol 1-20 and Jarcol 1-24.

According to a second particularly preferred embodiment, the oil which may be used to prepare the supramolecular compound in the context of the present invention is chosen from the esters of hydroxylated mono-, di- or tri-carboxylic acid and monoalcohols. and in particular: esters, in particular monoesters, of 12-hydroxystearic acid; such as octyl hydroxystearate and octyl-2-dodecyl hydroxystearate; mention may also be made of the corresponding oligomeric polyhydroxystearates, in particular having a degree of polymerization of 1 to 10, having at least one residual OH; esters of lactic acid, and in particular C4-40 alkyl lactates, such as 2-ethylhexyl lactate, diisostearyl lactate, isostearyl lactate, isononyl lactate, lactate, 2-octyldodecyl; malic acid esters, and in particular C4-40 alkyl malates, such as 2-diethyl hexyl malate, diisostearyl malate, 2-dioctyl dodecyl malate; esters of citric acid, and in particular C4-40 alkyl citrates, such as triisostearyl citrate, triisocetyl citrate and tri-isoarachidyl citrate.

According to this second preferred embodiment, the oil which can be used in the context of the present invention is preferably chosen from the esters of hydroxylated di-carboxylic acid and monoalcohols, and in particular of malic acid, and especially the C4-40 alkyl malates, such as 2-diethyl hexyl malate, diisostearyl malate, 2-dioctyl dodecyl malate.

In particular, when using glossy oils, the following brilliant oils can be employed, for which the refractive index at 25 ° C is indicated in parentheses: polyglyceryl-3-diisostearate (1.472), phytantriol (1.467 ), castor oil (1,475), octyl-2-dodecanol (1.46), oleyl alcohol (1.461), octyl hydroxystearate (1.46), polyglyceryl-2-isostearate (1,468), polyglyceryl-2-diisostearate (1,464), diisostearyl malate (1,462), butyl-2-octanol, 2-hexyl decanol (1.45), decyl-2-tetradecanol (1.457) , as well as their mixtures. Preferably, the oils which may be employed in the present invention for preparing the supramolecular compound are chosen from octyl-2-dodecanol, diisostearyl malate, butyl-2-octanol, 2-hexyl decanol and decyl. -2 tetradecanol; castor oil, hydrogenated or not, as well as its derivatives; hydroxylated modified soybean oil, and mixtures thereof. Junction Group The junction group that can be used to form the supramolecular compound of the compositions according to the invention carries at least one reactive group, in particular isocyanate or imidazole, which is capable of reacting with the reactive functional groups, in particular OH and / or NH 2 ( NH2 only for imidazole), oil, in order to form a covalent bond, especially of urethane type, between said oil and said joining group.

In a preferred manner, the linking group that can be used to form the supramolecular compound of the compositions according to the invention carries at least one reactive group, in particular isocyanate.

Said linking group is capable of establishing H bonds with one or more joint joining groups, of identical or different chemical nature, each pairing of a joining group involving at least 3 H (hydrogen) bonds, preferably minus 4 H bonds, preferably 4 H bonds For the purposes of the invention, the term "linking group" means any functional group comprising H bond donor or acceptor groups and capable of establishing at least three bonds. H, preferably at least 4 H bonds, preferably 4 H bonds, with a partner junction group, identical or not. For the purposes of the invention, the term "partner joining group" means any joining group capable of establishing H bonds with one or more joining groups of the same or another polymer according to the invention. The joining groups can be of identical or different chemical nature. If they are identical, they can then establish H links between them and are then called self-complementary join groups. If they are different, they are chosen so that they are complementary to the H interactions.

Said linking group, bearing isocyanate groups, can therefore be schematized (G) - (NCO) p, p being a non-zero integer, preferably equal to 1 or 2. The joining group also comprises at least one monovalent unit of formula (I) and / or at least one divalent unit of formula (II), as defined below: OO

embedded image in which: R 1 and R 3, which may be identical or different, represent a divalent carbon radical chosen from (i) a linear or branched C 1 -C 4 alkyl group; C32, (ii) a C4-C16 cycloalkyl group and (iii) a C4-C16 aryl group; optionally comprising 1 to 8 heteroatoms selected from O, N, S, F, Si and P; and / or optionally substituted by an ester, amide or 8 function with a C1-C12 alkyl radical; or a mixture of these groups; R 2 represents a hydrogen atom or a linear, branched or cyclic, saturated or unsaturated, optionally aromatic, C 1 -C 32 hydrocarbon (alkyl) radical, which may comprise one or more heteroatoms chosen from O, N, S; , F, Si and P.

Preferably, the linking group also comprises at least one monovalent unit of formula (I).

In particular, the radical R 1 may especially be: a linear or branched C2-C12 divalent alkylene group, especially a 1,2-ethylene, 1,6-hexylene, 1,4-butylene or 1,6- ( 2,4,4-trimethylhexylene), 1,4- (4-methylpentylene), 1,5- (5-methylhexylene), 1,6- (6-methylheptylene), 1,5- trimethylhexylene), 1,7- (3,7-dimethyloctylene). a divalent C 4 -C 12 cycloalkylene or arylene group, especially chosen from the following isophorone-, tolylene, 2-methyl-1,3-phenylene and 4-methyl-1,3-phenylene radicals; 4,4'-méthylènebiscyclohexylène; 4,4-bisphénylèneméthylène; or of structure: * CH 2 CH * Preferably, R 1 represents -isophorone-, - (CH 2) 6- or 4,4'-methylenebiscyclohexylene.

In particular, the radical R.sub.2 may in particular be H, or else: a C1-C32 alkyl group, in particular a C1-C16 or even a C1-C10 alkyl group; a C4-C12 cycloalkyl group; a C4-C12 aryl group; an aryl (C 4 -C 12) C 1 -C 13 alkyl group or a C 1 -C 4 alkoxy group; An arylalkoxy group, in particular a (C1-C4) aryl alkoxy group; a C4-C12 heterocycle or a combination of these radicals, which may optionally be substituted by an amino, ester and / or hydroxyl function. Preferably, R2 is H, CH3, ethyl, C13H27, C7H15, phenyl, isopropyl, isobutyl, n-butyl, tert-butyl, n-propyl, or -CH (C2H5) (C4H9).

Preferably, R 3 represents a divalent radical R 11 -C (O) -NH-R '4 - in which R' 3 and R '4, identical or different, represent a divalent carbon radical chosen from a linear alkyl group or branched C1-C32 or a C4-C16 cycloalkyl group or a C4-C16 aryl group; or their mixture. In particular, R '3 and R' 4 may represent methylene, 1,2-ethylene, 1,6-hexylene, 1,4-butylene, 1,6- (2,4,4-trimethylhexylene), 1,4 (4-methylpentylene), 1,5- (5-methylhexylene); 1,6- (6-méthylheptylène); 1,5- (2,2,5-trimethylhexylene), 1,7- (3,7-dimethyloctylene); 4,4'-méthylènebiscyclohexylène; 2-methyl-1,3-phenylene; 4-methyl-1,3-phenylene; 4,4'-bisphenylenemethylene; 1,2-tolylene, 1,4-tolylene, 2,4-tolylene, 2,6-tolylene; 1,5-naphthylene; tetramethylxylylene; isophorone. The term "isophorone" means the divalent radical of structure: ## STR2 ## In particular, R '3 may represent a C 1 -C 4 alkylene, in particular 1,2-ethylene. Preferably, R'4 may represent the divalent radical derived from isophorone.

In particular, R 3 can be of the following structure: ## STR2 ## In formula (I), it is particularly advantageous to have: ## STR5 ## R 2 = -isophorone, R 2 = methyl, which leads to the unit of formula H3C CH3-R, = - (CH2) 6-, R2 = methyl, which leads to the unit of formula: HH 1 1 ONN

## STR2 ## where R 2 = isopropyl, which leads to the unit of formula: H H 1 1 ONN

## STR5 ## where R 2 represents the formula: ## STR2 ## ## STR2 ## ## STR2 ## ## STR2 ## In a particularly preferred manner, in the formula (II), R.sup.1 represents the radical - isophorone-, R2 = methyl and R3 = - (CH2) 2000-NH-isophorone-, which leads to the divalent unit of formula: ## STR2 ## Junction groups carrying a single isocyanate function can be for-mule: O IN R2NNHiCiNHiR1iNCO HII o

wherein R1 and R2 are as defined above; and in particular: - R1 represents -isophorone-, - (CH2) 6-, -CH2CH (CH3) -CH2-C (CH3) 2 -CH2-CH2, 4,4'-methylenebiscyclohexylene, 2-methyl-1, 3-phenylene; and / or R2 is H, CH3, ethyl, C13H27, C7H15, phenyl, isopropyl, isobutyl, n-butyl, tert-butyl, n-propyl, or -CH (C2H5) (C4H9). Preferably, the linking groups may be chosen from the following groups: ## STR1 ## ## STR2 ##

The linking groups carrying two isocyanate functional groups may be of the formula: ## STR1 ## ## STR1 ## ## STR2 ##

Wherein R 1, R 2 and R 3 are as defined above, and in particular: R 1 represents -isophorone, - (CH 2) 2-, - (CH 2) 6-, -CH 2 CH (CH 3) -CH 2 -C (CH 3) 2-CH 2 -CH 2, 4,4'-methylenebiscyclohexylene, 2-methyl-1,3-phenylene; and / or - R2 is H, CH3, ethyl, C13H27, C7H15, phenyl, isopropyl, isobutyl, n-butyl, tert-butyl, n-propyl, or -CH (C2H5) (C4H9); and / or - R3 represents a divalent radical R '3 -O-C (O) -NH-R'4- in which R'3 and R'4, which are identical or different, represent a divalent carbon radical chosen from an alkyl group linear or branched C1-C30 or a C4-C12 cycloalkyl group or a C4-C12 aryl group; or their mixtures; and in particular R'3 represents a C1-C4 alkylene, especially 1,2-ethylene and R'4 represents the divalent radical derived from isophorone. A particularly preferred junction group is that of formula: ## STR2 ## Among the junction groups carrying an imidazole group, there may be mentioned the following compound: CH 3 HNO According to a particular embodiment of the invention, the Junction groups can be attached to the oil via functionalization of the junction group by an isocyanate or imidazole. According to another embodiment, it is possible to carry out the reverse reaction by pre-conditioning the oil with a diisocyanate.

As mentioned above (1st embodiment), the compound according to the invention can thus result from the chemical reaction between an oil (HB) - (OH) m (NH 2) n and a joining group (G) - (NCO ) p or (G) - (imidazole) p. Preferably, the oil comprises only hydroxyl functions and the linking group comprises 1 or 2 isocyanate functions, which leads to the following reactions: (HB) - (OH) m + OCN- (G) -NCO (HB ) -OC (O) NH- (G) -NHC (O) - (HB) (HB) - (OH) m + (G) -NCO (HB) -OC (O) NH- (G) with m = integer greater than or equal to 1. Preferably, the degree of grafting free OH of the oil is between 1 and 100%, especially between 20 and 99%, and more preferably between 50 and 95%; preferably, this level is 100% (all the free OH is functionalized by a linking group), especially when the oil initially comprises only one OH function. The supramolecular compound according to the invention can be prepared by the methods usually employed by those skilled in the art to form a urethane linkage, between the free OH functions of the oil and the isocyanate functional groups carried by the linking group. By way of illustration, a general method of preparation consists in: ensuring that the oil to be functionalized contains no residual water, heating the oil comprising at least one reactive function, in particular OH, to a temperature ranging from 60 ° C to 140 ° C; add the junction group carrying the reactive functions, in particular isocyanate; optionally stirring the mixture, under a controlled atmosphere, at a temperature of the order of 100-130 ° C .; for 1 to 24 hours; follow, by infrared spectroscopy, the disappearance of the isocyanate characteristic band (between 2500 and 2800 cm -1) so as to stop the reaction to the total disappearance of the peak, and then to allow the reaction to return to ambient temperature. final product. The reaction may be carried out in the presence of a solvent, especially methyltetrahydrofuran, tetrahydrofuran, toluene or butyl acetate; the reaction can also be carried out without solvent, the oil then being able to serve as a solvent.

It is also possible to add a conventional catalyst for urethane bond formation. By way of example, mention may be made of dibutyl tin dilaurate. The supramolecular compound can ultimately be washed and dried, or even purified, according to the general knowledge of those skilled in the art.

According to the second embodiment, the reaction may comprise the following steps: (i) functionalization of the oil with a diisocyanate according to the reaction scheme: (HB) -OH (1 eq.) + NCO-X-NCO (1 eq. ) (HB) -OC (O) -NH-X-NCO followed by (IIa) reaction with 6-methylisocytosine: Me Me (HB) -OC (O) -NX-NCO + N NH ^ NO ( HB) -OC (O) NiXNNNO or (iib) is reaction with 5-hydroxyethyl-6-methyl isocytosine: Me (HB) -OC (O) -NX-NCO + NOH-NH 2 N Me / v / N, x, N (0) CO- (HB) ON (HB) -OC (O) NiX, ONNNO An illustration of such a reaction is given in FOLMER et al., Adv. Mater, 12, 874-78 (2000). The supramolecular compounds of the compositions according to the invention can in particular respond to the following structures: the functionalized octyldodecanol ureidopyrimidone of structure: Or of structure: ## STR1 ## of structure: ## STR1 ## isostearyl - the ureidopyrimidone functionalized castor oil of structure: ## STR1 ## isostearyl ## STR1 ## where isostearyl isostearyl; structural good: OH - 2-hexyl decanol functionalized ureidopyrimidone structure: Or of structure: o N - the decyl-2 tetradecanol functionalized ureidopyrimidone structure: Or structure: O Nid NNÂ) NO .KHH It was found that the use of the compounds according to the invention can lead, after application of the composition to keratin materials, to the formation of a supermolecular polymer in the form of a network physically crosslinked, in particular through hydrogen bonds, generally in the form of a film, and having a very good mechanical strength. For the purposes of the invention, the term "supramolecular polymer" means a polymer chain or network formed from the assembly of non-polymeric compounds according to the invention with at least one other non-polymeric compound according to the invention, identical or different, each assembly comprising at least one pair of paired junction groups, identical or different. For the purposes of the invention, the term "pair of paired joining groups" means two joining groups, each of which may or may not be carried by the same compound according to the invention, the two groups being connected together via 4 Thus, the supramolecular polymer will have physical cross-linking points provided by the H bonds between these pairs of joining groups. The physical crosslinking will ensure the maintenance and persistence of the cosmetic effect in a manner analogous to the chemical crosslinking, while allowing reversibility, that is to say the possibility of completely eliminating the deposit.

Preferably, the supramolecular compound according to the invention has a viscosity, measured at 125 ° C., of between 30 and 6000 mPa.s, in particular between 150 and 4000 mPa.s, or even between 500 and 3500 mPa.s and even better between 750 and 3000 mPa.s. The number-average molecular weight (Mn) of the supramolecular compound according to the invention is preferably from 180 to 8000, preferably from 200 to 6000, even from 300 to 4000, and more preferably from 400 to 3000, preferably from 500 to 1500.

The supramolecular compound according to the invention is advantageously soluble in the oily cosmetic mediums usually employed, and in particular in vegetable oils, C 6 -C 32 alkanes, C 8 -C 32 fatty esters, C 2 -C 7 short esters, C8-C32 fatty alcohols, and more particularly in media comprising at least isododecane, Parleam, isononyl isononanoate, octyldodecanol, C12-C15 alkyl benzoate, butyl acetate, ethyl acetate, alone or in a mixture. By soluble is meant that the compound forms a clear solution in at least one solvent selected from isododecane, Parleam, isononyl isononanoate, octyldodecanol, C12-C15 alkyl benzoate, acetate butyl acetate, at least 50% by weight, at 25 ° C.

The supramolecular compounds according to the invention can advantageously be used in a cosmetic composition, which moreover comprises a cosmetically acceptable medium, that is to say compatible with keratin materials such as the skin of the face or body, the eyelashes, eyebrows, lips and nails.

Preferably, the composition according to the invention comprises a content of supramolecular compound of between 5% and 95% by weight, preferably between 10% and 95% by weight, and more preferably between 20% and 90% by weight. relative to the total weight of the composition.

By way of example of supramolecular compounds that can be used in the compositions according to the invention, mention may be made of the following compounds: Compound 1: Functionalized octvldodecanol ureidopyrimidone 70 g of ureidopyrimidone diisocyanate in methyl tetrahydrofuran are dissolved in argon. 80.3 g of octyldodecanol are added to 100 ml of dichloromethane under argon and then 15 microliters of dibutyltin dilaurate (catalyst). The reaction mixture is refluxed until the peak of the isocyanate (2250-2265 cm-1) disappears in I-spectrometry. The excess octyldodecanol is removed by washing the reaction medium with methanol, followed by three hours. extractions and drying on MgSO4. After evaporation of the organic phase, 103 g of a slightly yellow powder are obtained, characterized by 1 H NMR (conformal structure).

This powder may be carried in isododecane, for example at a concentration of 10% by weight; this concentration can range in particular up to 60% by weight in iso-45 dodecane, which then leads to a viscous but still manipulable solution. It is thus found that, by functionalization with a ureidopyrimidone, a liquid oil is passed to a solid which can be transported in isododecane at concentrations greater than 30%.

When a solution comprising 50% by weight of compound in isododecane is applied, after evaporation of the solvent, a transparent and glossy film is obtained, which has a good adherence by fragmentation, and a low resistance to friction.

Compound 2: Diisostearyl malate functionalized with a ureidopyrimidone 15 g (0.0234 mol) of diisostearyl malate are dried under reduced pressure at 80 ° C. for 4 hours. 7.21 g (0.0117 moles) of ureidopyrimidone diisocyanate dissolved in 60 ml of methyltetrahydrofuran and 12 μl of dilaurate dibutyltin catalyst are added. The mixture is heated at 95 ° C. under argon for 26 hours (disappearance of the characteristic band of isocyanates by IR spectroscopy). Methyl tetrahydrofuran (20 ml) is added to the reaction mixture and then filtered through Celite. After evaporation of the solvent and drying under reduced pressure, a pale yellow solid is obtained.

Compound 3: Castor oil functionalized with a ureidopyrimidone 15 g of castor oil (0.016 mole) are dried under reduced pressure at 80 ° C. for 4 hours. A solution of 4.9 g of ureidopyrimidone diisocyanate (0.008 mol) in 60 ml of methyltetrahydrofuran and 12 μl of dilaurate dibutyltin catalyst is added. The mixture is heated at 90 ° C. for 19 hours (complete disappearance of the isocyanate characteristic band by IR spectroscopy). At the end of the reaction, the solvent is evaporated and the resulting product is dried under reduced pressure at 35 ° C overnight.

A pale yellow solid gum is obtained.

Compound 4 (Comparative to Example 1): Octvldodecanol Functionalized with Isophorone OH + 1H 10 g of octyldodecanol are dried under reduced pressure at 80 ° C. for 2 hours, then 3.72 g of isophorone diisocyanate are added and 25 microliters of dibutyltin dilaurate catalyst. The mixture is heated to 95 ° C under argon. The disappearance of the isocyanate is followed by IR spectroscopy (disappearance of the band between 2250 and 2265 cm -1 after 12 hours of heating). A viscous oil is obtained which does not form a cohesive material. Compound 5 (Comparative to Example 2): Diisostearyl Malate Functionalized with Isophorone 10 g (0.0159 mol) of diisostearyl malate are dried under reduced pressure at 80 ° C. for 3 hours. 1.77 g (0.079 mol) of isophorone diisocyanate and 2.5 μl of catalyst (dibutyl tin dilaurate) are added under argon, and the reaction mixture is heated at 95 ° C. for 16 hours. During the reaction, the viscosity of the reaction medium increases. The reaction is stopped after the disappearance of the characteristic peak of the isocyanates by spectroscopy I R.

Compound 6 (Comparative to Example 3): Castor Oil Functionalized with Isophorone 15 g (0.016 mole) of castor oil are dried under reduced pressure at 80 ° C. for 6 hours. 1.78 g (0.008 mol) of isophorone diisocyanate and 12 μl of dilaurate dibutyltin catalyst are added, and the mixture is heated at 90 ° C. for 16 hours. The reaction is stopped after the disappearance of the characteristic peak of the isocyanates by IR spectroscopy.

EXAMPLE 7 The compounds prepared in Examples 1 to 6 are visually and to the touch, and the results are summarized in the following table: Physical Appearance Appearance of the film * of the compound Refractive index ** (Refractive index non-functionalized oil) Compound 1 Solid yellow Glossy and sticky film, which does not dewake; homogeneous deposit. Without transfer to the finger. 1.488 (1.46) Compound 4 Viscous oil Film that dews; non homogeneous deposition. Trans- transparent fertile finger. 1.474 (1.46) (comparative) Compound 2 Yellow solid Glossy film that does not stick; homogeneous deposition. Without transfer to the finger. 1.478 (1.462) Compound 5 Viscous oil Sticky glossy film that dews; non-homogeneous, transparent deposit. Without transfer to the finger. 1.4598 (1.462) (comparative) Compound 3 Yellow solid Glossy, slightly tacky film; behavior (solid gum) of a fragile solid, which does not dewake; homogeneous deposition. Without transfer to the finger. 1.4852 (1.48) Compound 6 Viscous oil Very tacky glossy film, which dews; homogeneous non-transparent deposit. Transfer to the finger. 1.4813 (1.48) (comparative) * The films are formed from a 40% by weight solution of the compound, either in isododecane for Examples 1-2 and 4-5, or in tetrahydrofuran for compounds 3 and 6. ** For refractive index measurements, all films are formed from a 40% by weight solution of the compound in tetrahydrofuran; the refractive index is measured after evaporation of the solvent.

The film which does not dewake means that after deposition and evaporation of the solvent, a true homogeneous continuous film is obtained. The film dewens means that after deposition and evaporation of the solvent, one obtains a film 'holes', non-homogeneous, non-continuous.

A tribometer test is carried out on these deposits / films: the films are formed from a 40% by weight solution in tetrahydrofuran by depositing on a nitrile elastomer and then drying for 24 hours at 25 ° C. The tests are carried out using a CSEM tribometer equipped with a 6mm diameter ball.15 This ball subjected to a load of 0.15N repeatedly rubs on a film (10 to 20 μm thick) . The speed of rotation of the disk is fixed at 6.3 cm / s which corresponds to a frequency of one revolution per second. The test is finished when the wear is total, or stopped after 1000 turns of solicitation. Remarks Compound 1 The film remains unchanged (homogeneous) for 300 turns (no wear or breakage); the material is therefore cohesive; behavior of a solid. Compound 4 No measurement possible: the material is loose, it behaves like an oil (comparative) Compound 2 The film remains unchanged (homogeneous) for 1000 turns (no wear or breakage); the material is therefore very cohesive and does not wear out. Compound 5 The material behaves like an oil, with a buttering effect when it is subjected to the wear test. (comparative) Example 3 The film is a little brittle but remains unchanged for 10 turns; after 10 turns, the wear is sharper; this reflects the behavior of a solid Compound 6 No measurement possible because no film formed ab initio: behavior of an oil (comparative) So we see that there is no decrease in the index of refraction after functionalization. The oil keeps its brilliant character, even functionalized. It has also been found that functionalization with ureidopyrimidones leads to films that are more or less sticky, but which do not transfer to the finger, unlike comparative films. In addition, and mainly, in the case of isophorone functionalized oils (comparative), the films dewake and do not form a homogeneous deposit. In contrast, the films obtained from the compounds according to the invention do not dewake and are homogeneous and cohesive. The tribometer results confirm the cohesion properties obtained with the compounds of the invention The functionalization with ureïdopyrimidones thus leads to sufficiently cohesive materials to be able to ensure a remanence of the deposit, which is otherwise brilliant, superior to the state of the art (isophorone). In summary: the brightness is constant, the cohesion of the improved deposit and therefore its amé-20 liorée.

Compound 8: Diisostearyl malate functionalized with a ureidopyrimidone

Preparation protocol Preparation of the supramolecular oil: diisostearyl malate functionalized with a ureidopyrimidone 150 g of diisostearyl malate was cast for 1 h 20 at 50 ° C. in a solution of 57.4 g isophorone diisocyanate and 38 g of methyl isocytosine, presence of dibutyltin dilaurate catalyst with exothermic control and inert atmosphere. Stirring was maintained for 55 minutes at 50 ° C after casting and then 50 ml propylene carbonate was added. The temperature of the reaction medium was then raised to 140 ° C. with a contact time of 2 hours, with stirring. The temperature of the reaction medium was then lowered to 70 ° C. and neutralized by addition of 30 ml of ethanol and the stirring was continued for one hour. After adding 780 ml of ethyl acetate, the mixture was filtered through celite. After evaporation of the ethyl acetate, 400 ml of cyclohexane were added to the reaction medium, and the mixture was washed twice with a mixture of H2O / EtOH (2 v / l) saturated with NaCl. The organic phase was then stripped with isododecane until a viscous liquid corresponding to the desired molecule at 50% solids content. For the purposes of the formulation, this dry extract may optionally be modified by adding isododecane to the medium. Compound 9: 2-hexyl decanol functionalized ureidopyrimidone OON% N N NO 1 IIHH 126.4 g of 2-hexyl decanol at 60 ° C under reduced pressure for 2 hours to dry. After 2 hours, the oil is allowed to return to 20 ° C. under argon, then added slowly over 5 hours to a mixture of 116 g of isophorone diisocyanate and 55 mg of DBTL catalyst at 50 ° C. At the end of the addition, the temperature of the reaction mixture is brought to 110 ° C, then 90 ml of propylene carbonate, and 78.4 g of 6-methyl isocytosine, which leads to a white suspension and homogeneous. Stirring is maintained at 110 ° C for two hours and the disappearance of the isocyanate is monitored by infrared spectroscopy. The disappearance of the peak at 2250 cm -1 is observed. In parallel, the disappearance of the amine from isocytosine is followed by an amine assay. At the end of the reaction, 500 g of isododecane are added at 100 ° C., and a slightly turbid pale yellow solution is obtained. 300 ml of ethanol are added and the stirring is maintained for 2 hours. After filtration on celite, the reaction mixture is stripped with isododecane at 80 ° C. in order to eliminate the alcohol and the propylene carbonate. Finally, the desired product is obtained, transported in isododecane at 50% solids content. The product is characterized in particular by HPLC and GPC (confirmed structure).

Compound 10: 2-hexyl decanol functionalized ureidopyrimidone 173.1 g of 2-hexyl decanol were heated at 60 ° C under reduced pressure for 2 hours to dry. After 2 hours, the oil is allowed to return to 50 ° C under argon and then slowly added over a period of 5 hours to a mixture of 158.7 g of isophorone diisocyanate and 77 mg of DBTL catalyst at 50 ° C. At the end of the addition, the temperature of the reaction mixture is brought to 110 ° C., then 150 ml of propylene carbonate and 60.3 g of 5-hydroxyethyl-6-methyl isocytosine are added, which leads to a suspension. white and homogeneous. Stirring is maintained at 110 ° C for five hours and the disappearance of the isocyanate is monitored by infrared spectroscopy. The disappearance of the peak at 2250 cm -1 is observed. At the end of the reaction, the temperature of the reaction medium is decreased to 100 ° C., and 780 g of isododecane are added; a slightly yellow turbid mixture is obtained. 100 ml of ethanol are added and stirring is continued for 2 hours. After filtration on celite, the reaction mixture is stripped with isododecane at 80 ° C. in order to eliminate the alcohol and the propylene carbonate. Finally, the desired product is obtained, transported in isododecane at 50% solids content. The product is characterized in particular by HPLC and GPC (confirmed structure).

Compound 11: 2-decyl tetradecanol functionalized ureidopyrimidone 126 g of 2-decyl tetradecanol are heated at 100 ° C under reduced pressure for 4 hours to dry. After 2 hours, the oil is added, over 4 hours at 50 ° C. and under argon, to a mixture of 94.7 g of isophorone diisocyanate and catalyst DBTL (qs). A follow-up by isocyanate determination makes it possible to follow the reaction; at half equivalence, 126 g of propylene carbonate and 53.3 g of 6-methyl isocytosine are added. Stirring and heating are maintained at 100 ° C for 16 hours and the disappearance of the isocyanate is monitored by infrared spectroscopy. The disappearance of the peak at 2250 cm -1 is observed. In parallel, the disappearance of the amine from isocytosine is followed by an amine assay. At the end of the reaction, the temperature is brought to 50 ° C, 100 ml of ethanol is added and the stirring is maintained for 5 hours. After filtration on celite and stripping with isododecane, the desired product is obtained, transported in isododecane at 50% solids content. The product is characterized in particular by GPC and HPLC coupled to a mass spectrum.

Compound 12: Jarcol 24 (J24) functionalized ureidopyrimidone

200 g of Jarcol 1-24 are cast at 50 ° C. in the IPDI (1.1 eq IPDI) in the presence of the catalyst, with control of the exotherm and under an inert atmosphere. The stirring is maintained after casting for 30 minutes at 50 ° C. 1.3 equivalents of methylisocytosine (MIC) are then added to the mixture, followed by the addition of 100 ml of propylene carbonate. The temperature of the reaction medium is then raised to 140 ° C., with a contact time of 1 h at 140 ° C. The disappearance of the isocyanate functions is monitored by infrared spectroscopy, then the temperature of the medium is lowered to 70 ° C. following the addition of 30 ml of ethanol and stirring for 1 hour. After addition of ethyl acetate, the medium is filtered on filter paper. After evaporation of the ethyl acetate, cyclohexane is added, followed by 5 washes with a saturated water mixture of NaCl / ethanol (2V / 1V). The organic phase is then dried over Na 2 SO 4, filtered and stripped with isododecane. A 50% solution of ex-dry oil product functionalized with a ureidopyrimidone is then obtained.

Compound 13: Jarcol 20 (J20) Functionalized Ureidopyrimidone

180 g of Jarcol 1-20 are cast at 50 ° C. in the IPDI (1, IPDI qq) in the presence of the catalyst) with exothermic control and under an inert atmosphere.

Stirring is maintained for 30 minutes at 50 ° C. 1.3 equivalents of MIC are added to the reaction medium followed by the addition of 100 ml of propylene carbonate. The temperature of the reaction medium is then raised to 140 ° C., and the stirring is maintained for 1 hour at 140 ° C. the reaction is done by infra-red spectroscopy, followed by the decrease of the characteristic peak of the isocyanate function. Decrease of the temperature to 70 ° C then addition of 30m1 of ethanol and agitation for 1h. After addition of ethyl acetate, the medium is filtered on filter paper. After evaporation of the ethyl acetate, cyclohexane is added, followed by 5 washes with a saturated water mixture of NaCl / ethanol (2V / 1V). The organic phase is then dried over Na 2 SO 4, filtered and stripped with isododecane. A 50% solution of oil solids functionalized with a ureidopyrimidone is then obtained.

Paste qras body The composition according to the invention comprises at least one pasty polar fatty substance.

For the purposes of the present invention, the term "pasty fatty substance" (also referred to as pasty fatty substance) is understood to mean a lipophilic fat compound with a reversible solid / liquid state change, having in the solid state an anisotropic crystalline organization and comprising at least one the temperature of 23 ° C a liquid fraction and a solid fraction. In other words, the starting melting temperature of the pasty compound may be less than 23 ° C. The liquid fraction of the pasty compound measured at 23 ° C. can represent 9 to 97% by weight of the compound. This liquid fraction at 23 ° C is preferably between 15 and 85%, more preferably between 40 and 85% by weight.

For the purposes of the invention, the melting temperature corresponds to the temperature of the most endothermic peak observed in thermal analysis (DSC) as described in ISO 11357-3; 1999. The melting point of a paste or a wax can be measured using a differential scanning calorimeter (DSC), for example the calorimeter sold under the name "MDSC 2920" by the company TA Instruments .

The measurement protocol is as follows: A sample of 5 mg of paste or wax (as the case may be) placed in a crucible is subjected to a first temperature rise from -20 ° C to 100 ° C, at the rate of 10 ° C / minute, then cooled from 100 ° C to -20 ° C at a cooling rate of 10 ° C / minute and finally subjected to a second temperature rise from -20 ° C to 100 ° C. ° C at a heating rate of 5 ° C / minute. During the second temperature rise, the variation of the power difference absorbed by the empty crucible and the crucible containing the pasty or wax sample is measured as a function of temperature. The melting point of the compound is the value of the temperature corresponding to the apex of the peak of the curve representing the variation of the difference in power absorbed as a function of the temperature. The liquid fraction by weight of the pasty compound at 23 ° C. is equal to the ratio of the enthalpy of fusion consumed at 23 ° C. to the heat of fusion of the pasty compound. The heat of fusion of the pasty compound is the enthalpy consumed by the compound to pass from the solid state to the liquid state. The pasty compound is said to be in the solid state when the entirety of its mass is in crystalline solid form. The pasty compound is said to be in a liquid state when all of its mass is in liquid form. The melting enthalpy of the pasty compound is equal to the area under the curve of the thermogram obtained using a differential scanning calorimeter (DS C), such as the calorimeter sold under the name MDSC 2920 by the company TA instrument, with a temperature rise of 5 or 10 ° C per minute, according to the standard ISO 11357-3: 1999. The enthalpy of fusion of the pasty compound is the amount of energy required to pass the compound from the solid state to the liquid state. It is expressed in J / g. The enthalpy of fusion consumed at 23 ° C. is the amount of energy absorbed by the sample to pass from the solid state to the state that it has at 23 ° C. consisting of a liquid fraction and a solid fraction. The liquid fraction of the pasty compound measured at 32 ° C is preferably 30 to 100% by weight of the compound, preferably 50 to 100%, more preferably 60 to 100% by weight of the compound. When the liquid fraction of the pasty compound measured at 32 ° C is 100%, the temperature of the end of the melting range of the pasty compound is less than or equal to 32 ° C. The liquid fraction of the pasty compound measured at 32 ° C. is equal to the ratio of the enthalpy of fusion consumed at 32 ° C. to the heat of fusion of the pasty compound. The heat of fusion consumed at 32 ° C. is calculated in the same way as the enthalpy of fusion 40 consumed at 23 ° C.

By pasty "polar", within the meaning of the present invention, is meant a pasty whose solubility parameter at 25 ° C Sa is different from 0 (J / cm3) 'Y'. In particular, pasty "polar" means a pasty substance whose chemical structure is formed essentially or even consisting of carbon and hydrogen atoms, and comprising at least one highly electronegative heteroatom such as an atom of oxygen, nitrogen, or phosphorus.

The definition and calculation of the solubility parameters in the HANSEN tridimensional solubility space are described in the article by C. M. Hansen: "The three dimensional solubility parameters" J. Paint Technol. 39, 105 (1967). According to this Hansen space: - 8D characterizes the LONDON dispersion forces resulting from the formation of dipoles induced during molecular shocks; 55 - 6p characterizes the DEBYE interaction forces between permanent dipoles as well as the KEESOM interaction forces between induced dipoles and permanent dipoles; - Sh characterizes the specific interaction forces (hydrogen bond, acid / base, donor / acceptor type, etc.); - Sa is determined by the equation: Sa = (81,2 + 6h2) 'Y' The parameters 8p, 8h, 8D and Sa are expressed in (J / cm3) '4.

Preferably, the pasty polar fatty substances are hydrocarbon-based.

The term "hydrocarbonaceous pasty fatty substance" means a pasty fatty substance essentially consisting of, and possibly consisting of, carbon and hydrogen atoms, and possibly oxygen, nitrogen, and non-carbon atoms. atom of silicon or fluorine. It may contain alcohol, ester, ether, carboxylic acid, amine and / or amide groups.

The pasty compound is preferably chosen from synthetic compounds and compounds of plant origin. A pasty compound can be obtained synthetically from starting materials of plant origin. The pasty compound is advantageously chosen from - lanolin and its derivatives - polyol ethers chosen from pentaerythritol ethers and polyalkylene glycol ethers, fatty alcohol and sugar ethers, and mixtures thereof. pentaerythritol ether and polyethylene glycol comprising 5 oxyethylenated units (50E) (CTFA name: PEG-5 Pentaerythrityl Ether), pentaerythritol ether and polypropylene glycol comprising 5 oxypropylene units (5 PO) (CTFA name: PPG- 5 Pentaerythrityl Ether), and mixtures thereof, and more particularly the PEG-5 Pentaerythrityl Ether mixture, PPG-5 Pentaerythrityl Ether and soybean oil, sold under the name "Lanolide" by the company Vevy, a mixture in which the constituents are in a ratio by weight 46/46/8: 46% PEG-5 Pentaerythrityl Ether, 46% PPG-5 Pentaerythrityl Ether and 8% soybean oil. vinyl polymers, in particular: linear or branched oligomers, homo or copolymers of alkyl (meth) acrylates preferably having a C 8 -C 30 alkyl group; homo and copolymeric oligomers of vinyl esters having alkyl groups containing C8-C30 • copolymers of vinylpyrrolidone / eicosene (INCI name VP / eicosene copolymer), for example sold by the company ISP under the trade name Ganex V220F®, • oligomers homo and copolymers of vinyl ethers having C8-C30 alkyl groups the liposoluble polyethers resulting from the polyetherification between one or more C2-C100 diols, preferably C2-C50 diols, the esters, and / or their mixtures. The pasty compound is preferably a polymer, in particular a hydrocarbon polymer.

Among the liposoluble polyethers, copolymers of ethylene oxide and / or of propylene oxide with long-chain C 6 -C 30 alkylene oxides are preferred, more preferably such as the weight ratio of ethylene oxide. and / or propylene oxide with alkylene oxides in the copolymer is from 5:95 to 70:30. In this family, mention will in particular be made of copolymers such as long-chain alkylene oxides are arranged in blocks having an average molecular weight of 1,000 to 10,000, for example a polyoxyethylene / polydodecyl glycol block copolymer such as dodecane-diol ethers. (22 mol) and polyethylene glycol (45 0E) marketed under the trademark ELFACOS ST9 by Akzo Nobel.

Among the esters, the following are particularly preferred: esters of an oligomeric glycerol, in particular the diglycerol esters, in particular the condensates of adipic acid and of glycerol, for which part of the hydroxyl groups of the glycerols have reacted with a mixture of fatty acids such as stearic acid, capric acid, stearic acid and isostearic acid and 12-hydroxystearic acid, especially in the image of those marketed under the trademark Softisan 649 by the company Sasol - arachidyl propionate marketed under the trademark Waxenol 801 by Alzo, - phytosterol esters, - triglycerides of fatty acids and their derivatives - pentaerythritol esters - non-crosslinked polyesters resulting from the polycondensation between a dicarboxylic acid or a C 4 -C 50 linear or branched polycarboxylic acid and a C 2 -C 50 diol or polyol, the ester aliphatic esters resulting from the esterification of a hydroxycarboxylic acid ester than aliphatic by an aliphatic carboxylic acid. Preferably, the aliphatic carboxylic acid comprises from 4 to 30 and preferably from 8 to 30 carbon atoms. It is preferably selected from hexanoic acid, heptanoic acid, octane acid, 2-ethyl hexanoic acid, nonanoic acid, decanoic acid, undecanoic acid, dodecanoic acid, tridecanoic acid, tetradecanoic acid, pentadecanoic acid, hexadecanoic acid, hexydecanoic acid, heptadecanoic acid, octadecanoic acid, isostearic acid, nonadecanoic acid, eicosanoic acid, isoarachidic acid, octyldodecanoic acid, henicosanoic acid, docosanoic acid, and mixtures thereof. The aliphatic carboxylic acid is preferably branched. The aliphatic hydroxy carboxylic acid ester is advantageously derived from a hydroxylated aliphatic carboxylic acid having from 2 to 40 carbon atoms, preferably from 10 to 34 carbon atoms and better still from 12 to 28 carbon atoms, and from 1 to to 20 hydroxyl groups, preferably 1 to 10 hydroxyl groups and more preferably 1 to 6 hydroxyl groups. The aliphatic hydroxy carboxylic acid ester is chosen from: a) partial or total esters of saturated linear monohydroxylated aliphatic monocarboxylic acids; b) partial or total esters of unsaturated monohydroxylated aliphatic monocarboxylic acids; c) partial or total esters of saturated monohydroxylated aliphatic polycarboxylic acids; d) partial or total esters of saturated polyhydroxylated aliphatic polycarboxylic acids; e) the partial or total esters of C2 to C16 aliphatic polyols reacted with a mono or polyhydroxylated aliphatic mono or poly carboxylic acid, and mixtures thereof. the esters of diol dimer and diacid dimer, if appropriate, esterified on their function (s) alcohol (s) or acid (s) free (s) by acidic radicals or alcohols, especially dimer esters Dilinoleate, such esters may be chosen in particular from the following INCI nomenclature: bis-behenyl / isostearyl / phytosteryl dimerdilinyl dimerdilinoleate (Plandool G), phytosteryl isostearyl dimerdilinoleate (Lusplan PI-DA, Lusplan PHY / IS -DA), phytosteryl / isosteryl / cetyl / stearyl / behenyl dimerdilinoate (Plandool H or Plandool S), and mixtures thereof. the hydrogenated rosinate esters, such as the dilinoleyl dimers of hydrogenated rosinate (Lusplan DD-DHR or DD-DHR from Nippon Fine Chemical), and mixtures thereof.

Advantageously, the pasty polar compound (s) preferably represents 0.1 to 80%, better still 0.5 to 60%, better still 1 to 30% and better still 1 to 20% by weight relative to the total weight of the composition.

Additional pasty fatty substances: The composition according to the invention may also comprise, in addition to the polar pasty fatty substance, an additional pasty fatty substance, such as an apolar pasty fatty substance for example.

For the purposes of the present invention, the term "apolar pasty fatty substance" means a pasty fatty substance whose solubility parameter at 25 ° C. as defined below, Sa is equal to 0 (J / cm 3) 4. Non-polar pasty fatty substances are, in particular, pasty hydrocarbon fatty substances consisting solely of carbon and hydrogen atoms and free of heteroatoms such as N, O, and P.

Preferably, the composition according to the invention is free of apolar pasty fatty substance.

COLORING MATERIALS According to a particularly preferred embodiment, the composition according to the invention comprises at least one dyestuff, preferably in a content of at least 0.1% by weight relative to the total weight of the composition. The coloring material may be chosen from pulverulent dyestuffs (in particular pigments and pearlescent agents) and water-soluble or liposoluble dyestuffs. By pigments within the meaning of the invention is meant white or colored particles, mineral or organic, insoluble in an aqueous solution, intended to color and / or opacify the resulting makeup film. The pigments also include nacres or pearlescent pigments. The pigments may be present in a proportion of from 0.1 to 15% by weight, especially from 1 to 10% by weight, and in particular from 2 to 8% by weight, relative to the total weight of the cosmetic composition. As inorganic pigments that may be used in the invention, mention may be made of titanium, zirconium or cerium oxides, as well as zinc, iron or chromium oxides, ferric blue, manganese violet, ultramarine blue and Chromium hydrate. According to one embodiment, titanium oxides and iron oxides are more particularly considered in the invention. According to one embodiment, a pigment which is suitable for the invention may in particular be based on titanium dioxide and iron oxide. It may also be a pigment having a structure which may for example be sericite / brown iron oxide / titanium dioxide / silica. Such a pigment is marketed for example under the reference COVERLEAF NS or JS by CHEMICALS AND CATALYSTS and has a contrast ratio of about 30.

A pigment suitable for the invention may comprise a structure which may be, for example, silica microsphere type containing iron oxide. An example of a pigment having this structure is that marketed by MIYOSHI under the reference PC BALL PC-LL-100P, this pigment consisting of silica microspheres containing yellow iron oxide.

Among the organic pigments that can be used in the invention, mention may be made of carbon black, D & C type pigments, lacquers based on cochineal carmine, barium, strontium, calcium, aluminum or diketo pyrrolopyrroles (DPP). ) described in EP-A-542669, EP-A-787730, EP-A-787731 and WO-A-96/08537. By "nacres" or "pearlescent pigments", it is necessary to include colored particles of any shape, iridescent or otherwise, in particular produced by certain shellfish in their shell or else synthesized and which exhibit a color effect by optical interference. The nacres can be chosen from pearlescent pigments, such as titanium mica coated with an iron oxide, titanium mica coated with bismuth oxychloride, titanium mica coated with chromium oxide, titanium mica coated with with an organic dye, as well as pearlescent pigments based on bismuth oxychloride. It may also be mica particles on the surface of which are superimposed at least two successive layers of metal oxides and / or organic dyestuffs. Mention may also be made, by way of example of nacres, of natural mica coated with titanium oxide, with iron oxide, with natural pigment or with bismuth oxychloride. Among the nacres available on the market, mention may be made of mother-of-pearl TIMICA, FLAMENCO and DUOCHROME (based on mica) marketed by ENGELHARD, TIMIRON pearls marketed by MERCK, mother-of-pearl containing PRESTIGE mica marketed by the company. ECKART and nacres based on SUNSHINE synthetic mica sold by the company SUN CHEMICAL. The nacres may more particularly have a color or a yellow, pink, red, bronze, orange, brown, gold and / or coppery reflection. As an illustration of the nacres that can be used in the context of the present invention, mention may be made, in particular, of gold-colored nacres, in particular sold by Engelhard under the name Brillant gold 212G ( Timica), 222C Gold (Cloisonne), Sparkle Gold (Timica), Gold 4504 (Chromalite) and Monarch Gold 233X (Cloisonne); bronze nacres, in particular, sold by the company Merck under the names Bronze Fine (17384) (Colorona) and Bronze (17353) (Colorona) and by Engelhard under the name Super Bronze (Cloisonne); orange nacres, in particular, sold by ENGELHARD under the name Orange 363C (Cloisonne) and Orange MCR 101 (Cosmica) and by MERCK under the name Passion orange (Colorona) and Matte orange (17449) (Microna); brown-colored pearlescent agents, in particular, sold by ENGELHARD under the name Nu-antique copper 340XB (Cloisonne) and Brown CL4509 (Chromalite); nacres with a copper sheen, in particular, marketed by Engelhard under the name Copper 340A (Timica); the red-colored pearlescent agents, in particular, marketed by MERCK under the name Sienna fine (17386) (Colorona); yellow-colored pearlescent agents, in particular, marketed by Engelhard under the name Yellow (4502) (Chromalite); red-colored pearlescent agents with a gold glint, in particular sold by Engelhard under the name Sunstone G012 (Gemtone); pink nacres, in particular, sold by ENGELHARD under the name Tan opal G005 (Gemtone); black nacres with gold reflection, sold by the company Engelhard under the name Nu antique bronze 240 AB (Timica), blue pearls, in particular, sold by MERCK under the name Matte Blue (17433) (Microna), white nacres with silvery reflection, in particular, sold by the company Merck under the name Xirona Silver and the golden-green orange-colored mother-of-pearl, in particular, marketed by MERCK under the name Indian summer (Xirona) and their mixtures. According to an alternative embodiment, a composition of the invention may comprise, as pigments, a pigment chosen from titanium dioxide, pigments based on titanium dioxide and iron oxide, or pigments based on dioxide. titanium, such as sericite / brown iron oxide / titanium dioxide / silica, natural mica coated with titanium oxide, and mixtures thereof.

A composition according to the invention may further comprise at least one dyestuff that is distinct from the pigments as defined above. Such a coloring material may be chosen from organic or inorganic, liposoluble or water-soluble dyestuffs, materials with specific optical effect and mixtures thereof.

A cosmetic composition according to the invention may thus also comprise water-soluble or fat-soluble dyes. Liposoluble dyes are, for example, Sudan Red, DC Red 17, DC Green 6, [3-carotene, soybean oil, Sudan Brown, DC Yellow 11, DC Violet 2, DC orange 5 and yellow quinoline. The water-soluble dyes are, for example, beet juice and methylene blue.

A cosmetic composition according to the invention may also contain at least one material with a specific optical effect. This effect is different from a simple conventional hue effect, i.e. unified and stabilized as produced by conventional dyestuffs, such as, for example, monochromatic pigments. For the purposes of the invention, "stabilized" means devoid of effect of color variability with the angle of observation or in response to a change of temperature. For example, this material may be chosen from particles with a metallic sheen, goniochromatic coloring agents, diffractive pigments, thermochromic agents, optical brighteners, and especially interferential fibers.

The particles with a metallic sheen that can be used in the invention are in particular chosen from: particles of at least one metal and / or at least one metal derivative, particles comprising an organic or inorganic substrate, monomaterial or multimaterial, at least partially covered by at least one metal-reflecting layer comprising at least one metal and / or at least one metal derivative, and - mixtures of said particles. Among the metals that may be present in said particles, mention may be made, for example, of Ag, Au, Cu, Al, Ni, Sn, Mg, Cr, Mo, Ti, Zr, Pt, Va, Rb, W, Zn, Ge, Te. Se and their mixtures or alloys. Ag, Au, Cu, Al, Zn, Ni, Mo, Cr, and mixtures or alloys thereof (e.g., bronzes and brasses) are preferred metals. The term "metal derivatives" denotes compounds derived from metals, in particular oxides, fluorides, chlorides and sulphides. As an illustration of these particles, mention may be made of aluminum particles, such as those sold under the names STARBRITE 1200 EAC® by the company 25 SIBERLINE and METALURE® by the company ECKART. Mention may also be made of copper metal powders or mixtures of alloys, such as the references 2844 sold by the company Radium Bronze, metallic pigments, such as aluminum or bronze, such as those sold under the trade names ROTOSAFE 700 ECKART, the silica-coated aluminum particles marketed under the name VISIONAIRE BRIGHT SILVER from ECKART and the metal alloy particles, such as bronze powder (al-copper and zinc alloy) coated with silica marketed under the name of Visionaire Bright Natural Gold from Eckart. It may also be particles comprising a glass substrate such as those marketed by the company NIPPON SHEET GLASS under the names MICROGLASS METASHINE. The goniochromatic coloring agent may be selected from, for example, interfering multilayer structures and liquid crystal coloring agents. Examples of symmetrical interferential multilayer structures that can be used in compositions produced in accordance with the invention are, for example, the following structures: Al / SiO 2 / Al / SiO 2 / Al, pigments having this structure being marketed by Dupont. FROM NEMOURS; Cr / MgF 2 / Al / MgF 2 / Cr, pigments having this structure being marketed under the name CHROMAFLAIR by the company FLEX; MoS2 / SiO2 / AI / SiO2 / MoS2; Fe2O3 / SiO2 / Al / SiO2 / Fe2O3, and Fe2O3 / SiO2 / Fe2O3 / SiO2 / Fe2O3, pigments having these structures being marketed under the name SICOPEARL by BASF; MoS2 / SiO2 / mica-oxide / SiO2 / MoS2; Fe2O3 / SiO2 / micaoxide / SiO2 / Fe2O3; TiO2 / SiO2 / TiO2 and TiO2 / Al2O3 / TiO2; SnO / TiO2 / SiO2 / TiO2 / SnO; Fe2O3 / SiO2 / Fe2O3; SnO / mica / TiO 2 / SiO 2 / TiO 2 / mica / SnO, pigments having these structures being sold under the name XIRONA by the company MERCK (Darmstadt). By way of example, these pigments may be the pigments of silica / titania / tin oxide structure sold under the name Xirona Magic by the company Merck, the silica / brown iron oxide structural pigments marketed under the name XIRONA. INDIAN SUMMER by the company MERCK and the silica / titanium oxide / mica / tin oxide structural pigments marketed under the name XIRONA 55 CARRIBEAN BLUE by MERCK. Mention may also be made of the INFINITE COLORS pigments from SHISEIDO. Depending on the thickness and nature of the different layers, different effects are obtained. Thus, with the Fe.sub.2 O.sub.3 / SiO.sub.2 / Al.sub.2 / SiO.sub.2 / Fe.sub.2 O.sub.3 structure, grey-green to gray-red is passed for SiO.sub.2 layers of 320 to 350 nm; from red to golden for layers of SiO2 from 380 to 400 nm; from violet to green for SiO2 layers from 410 to 420 nm; from copper to red for SiO2 layers from 430 to 440 nm. Mention may be made, by way of example of pigments with a polymeric multilayer structure, those marketed by the company 3M under the name COLOR GLITTER. As liquid crystal goniochromatic particles, it is possible to use, for example, those sold by CHENIX, as well as those marketed under the name HELICONE® HC by WACKER.

The dyestuffs, in particular the pigments treated with a hydrophobic agent, may be present in the composition in a content ranging from 0.1% to 50% by weight, relative to the total weight of the composition, preferably ranging from 5% to 30% by weight, and preferably from 1% to 20% by weight.

Volatile oil

The composition according to the invention may comprise at least one volatile oil. Within the meaning of the invention, a volatile oil has at ambient temperature (25 ° C.) and atmospheric pressure (760 mmHg) a vapor pressure ranging from 0.02 mm to 300 mmHg (2.66 Pa). 40,000 Pa) and better ranging from 0.1 to 90 mm Hg (13 Pa to 12,000 Pa). The nonvolatile oils then correspond to a vapor pressure of less than 0.02 mmHg (2.66 Pa), and more preferably less than 10-3 mmHg (0.13 Pa). The volatile oil may be a silicone oil, a hydrocarbon oil or a fluorinated oil. at. Silicone oil According to a variant of the invention, the liquid fatty phase comprises at least one volatile silicone oil. By "silicone oil" is meant an oil comprising at least one silicon atom, and in particular comprising Si-O groups.

The volatile silicone oil that may be used in the invention may be chosen from silicone oils having a flash point ranging from 40 ° C. to 150 ° C., preferably having a flash point greater than 55 ° C. and less than or equal to 105 ° C, and preferably ranging from 65 ° C to 95 ° C. The flash point is in particular measured according to the ISO 3679 standard. The volatile silicone oil may be chosen from linear or cyclic silicone oils such as linear or cyclic polydimethylsiloxanes (PDMS) having from 3 to 7 silicon atoms. By way of example of such oils, mention may be made of octyltrimethicone, hexyltrimethicone, decamethylcyclopentasiloxane (cyclopentasiloxane or D5), octamethylcyclotetrasiloxane (cyclotetradimethylsiloxane or D4), dodecamethylcyclohexasiloxane (D6) and decamethyltetrasiloxane (L4). , KF 96 A from Shin Etsu, polydimethyl siloxanes such as those sold under the reference DC 200 (1.5 cSt), DC 200 (5 cSt), DC 200 (3 cSt) by Dow Corning.

b. Hydrocarbon Oil According to one variant of the invention, the liquid fatty phase comprises at least one volatile hydrocarbon oil. By "hydrocarbon oil" is meant an oil formed essentially, or even constituted, of carbon and hydrogen atoms, and possibly of oxygen, nitrogen, and not containing a silicon atom or fluorine. It may contain alcohol, ester, ether, carboxylic acid, amine and / or amide groups. The volatile hydrocarbon oils (also called solvents) may be chosen from hydrocarbon-based oils having 8 to 16 carbon atoms, and especially C8-C16 branched alkanes such as C8-C16 isoalkanes of petroleum origin (also known as isoparaffins). ) such as isododecane (also called 2,2,4,4,6-pentamethylheptane), isodecane, isohexadecane, and for example the oils sold under the trade names Isopars' or permetyls, branched esters C8-C16 isohexyl neopentanoate, and mixtures thereof. Other volatile hydrocarbon oils such as petroleum distillates, in particular those sold under the name Shell or by Shell, can also be used. Preferably, the volatile solvent is chosen from volatile hydrocarbon oils having from 8 to 16 carbon atoms and mixtures thereof. As other volatile hydrocarbon solvents (oils) that can be used in the composition according to the invention, mention may also be made of ketones which are liquid at ambient temperature, such as methyl ethyl ketone or acetone; short-chain esters (having from 3 to 8 carbon atoms in total) such as ethyl acetate, methyl acetate, propyl acetate, n-butyl acetate; ethers which are liquid at ambient temperature, such as diethyl ether, dimethyl ether or dichlorodiethyl ether; alcohols and in particular linear or branched lower monoalcohols having from 2 to 5 carbon atoms, such as ethanol, isopropanol or n-propanol.

Preferably, the composition has a volatile oil content greater than 5% by weight, preferably ranging from 5% to 50% by weight and ranging from 10% to 35% by weight by weight relative to the total weight of the composition.

In a preferred embodiment, the volatile oil has a flash point greater than 65 ° C, and more preferably greater than 80 ° C. By way of example of such a volatile oil, mention may be made of isohexadecane.

Non-volatile oils The composition according to the invention may comprise at least one non-volatile oil. This may in particular be chosen from hydrocarbon oils and / or silicone oils and / or fluorinated non-volatile, and preferably from hydrocarbon oils. The term "non-volatile oil" means an oil remaining on the skin or the keratinous fiber, more generally on the keratin material, at ambient temperature and atmospheric pressure, for at least several hours and having in particular a vapor pressure of less than 10 -3. mm Hg (0.13 Pa). It is also possible to define a non-volatile oil as having an evaporation rate such that under the conditions defined above, the amount evaporated after 30 minutes is less than 0.07 mg / cm 2.

These oils can be of vegetable, mineral or synthetic origin. Non-volatile hydrocarbon oils that may especially be mentioned include: hydrocarbon-based oils of vegetable origin, such as triglycerides consisting of esters of fatty acids and of glycerol, the fatty acids of which may have chain lengths varying from C 4 to C24, the latter may be linear or branched, saturated or unsaturated, such as triglycerides of heptanoic acids, octanoic; these oils include wheat germ, sunflower, grape seed, sesame, maize, apricot, castor, shea, avocado, olive, soya, sweet almond, palm, rapeseed, cotton, hazelnut, macadamia, jojoba, alfalfa, poppy, pumpkin, sesame, pumpkin, rapeseed, blackcurrant, evening primrose, millet, barley, quinoa, rye, safflower, bancoulier, passiflora, muscat rose; or the triglycerides of caprylic / capric acids, such as those sold by the company Stéarineries Dubois or those sold under the names "Miglyol 810®", "812®" and "818®" by the company Dynamit Nobel, - synthetic ethers ; linear or branched hydrocarbons of mineral or synthetic origin, such as paraffin oil or its derivatives, petroleum jelly, hydrogenated polyisobutene such as Parleam® sold by the company Nippon Oil Fats, squalane, polybutylenes such as INDOPOL H-100 (molar mass or MW = 965 g / mol), INDOPOL H-300 (MW = 1340 g / mol), INDOPOL H-1500 (MW = 2160 g / mol) marketed or manufactured by the company AMOCO, hydrogenated polyisobutylenes such as PANALANE H-300 E marketed or manufactured by AMOCO (MW = 1340 g / mol), Viseal 20000 sold or manufactured by SYNTEAL (MW = 6000 g / mol) , REWOPAL PIB 1000 marketed or manufactured by WITCO (MW = 1000 g / mol), polydecenes and hydrogenated polydecenes such as: PURESYN 10 (MW = 723 g / mol), PURESYN 150 (MW = 9200 g) mol) marketed or manufactured by MOBIL CHEMICALS, and mixtures thereof; esters of fatty acids, in particular from 4 to 22 carbon atoms, and in particular of octanoic acid, heptanoic acid, lanolic acid, oleic acid, lauric acid and stearic acid, for example propylene glycol dioctanoate, propylene glycol monoisostearate, poly-glyceryl 2-diisostearate, neopentyl glycol diheptanoate, synthetic esters such as oils of formula R 1 COOR 2 in which R represents the residue of a linear fatty acid or branched chain containing from 1 to 40 carbon atoms and R2 represents a particularly branched hydrocarbon chain containing from 1 to 40 carbon atoms, provided that R, + R2 is 11, for example purcellin oil (cetostearyl octanoate), isononyl isononanoate, C12-C15 alcohol benzoate, 2-hexyl ethyl palmitate, 2-octyl dodecyl stearate, 2-octyl dodecyl erucate, isostearyl isostearate , octyl-2-dodecyl benzoate, octanoates, decanoates or ricinoleates of alcohols or polyalcohols, isopropyl myristate, isopropyl palmitate, butyl stearate, hexyl laurate, 2-ethylhexyl palmitate, 2-hexyl-decyl laurate, 2-octyl decyl palmitate, 2-octyldodecyl myristate, isodecyl neopentanoate; hydroxylated esters such as isostearyl lactate, octyl hydroxystearate, octyldodecyl hydroxystearate, diisostearyl malate, triisocetyl citrate, glycerol or diglycerine triisostearate; diethylene glycol diisononanoate; and pentaerythritol esters such as pentaerythrityl tetra decyl tetradecanoate (MW = 1538 g / mol), pentaerythrityl tetraisostearate (MW = 1202 g / mol), pentaerythrityl tetraisonanoate (MW = 697 g / mol), esters of aromatic acids and of alcohols comprising 4 to 22 carbon atoms, in particular tridecyl trimellitate, a polyester resulting from the esterification of at least one triglyceride of carboxylic acid (s); ) hydroxylated with an aliphatic monocarboxylic acid and an optionally unsaturated aliphatic dicarboxylic acid, such as castor oil of succinic acid and isostearic acid sold under the reference Zénigloss by Zenitech, - esters of diol dimer and of diacid dimer of the general formula HO-R '- (- 000-R2-COO-R' -) h-OH, in which: R 'represents a residue of diol dimer obtained by hydrogenation of the dilinoleic diacid R2 represents a dilinoleic diacid residue hydrogenated, and h rep an integer ranging from 1 to 9, in particular the esters of dilinoleic diacids and of dilinoleic diol dimers marketed by NipPON FINE CHEMICAL under the trademark LUSPLAN DD-DA5® and DD-DA7®,

copolymers of vinylpyrrolidone / 1-hexadecene, for example sold under the name ANTARON V216 by the company ISP (MW = 7300 g / mol),

- The branched-chain and / or unsaturated carbon-chain liquid fatty alcohols having from 8 to 26 carbon atoms, for instance oleic alcohol, linoleic or linolenic alcohol, isostearyl alcohol or octyl dodecanol; Higher C8-C26 fatty acids such as oleic acid, linoleic acid, linolenic acid, or isostearic acid; - and their mixtures.

The non-volatile silicone oils that may be used in the composition according to the invention may be silicone oils, such as phenyl silicone oils (also called phenyl silicone oil), for instance trimethylsiloxyethylene dimethicone sold under the reference Belsil PDM 1000 from the company Wacker. (MW = 9000 g / mol), or 1,3,5-trimethyl 1,1,3,5,5-pentaphenyl trisiloxane, sold by Dow Corning under the reference (PH-1555 HRI Dow Corning, name INCI: trimethylpentaphenyl trisiloxane). INCI name: trimethyl pentaphenyl trisiloxane), phenyl trimethicones (such as phenyl trimethicone sold under the trade name DC556 by Dow Corning), phenyl dimethicones, phenyl trimethylsiloxy diphenyl siloxanes, diphenyl dimethicones, diphenyl methyldiphenyl trisiloxanes, polydimethylsiloxanes ( Non-volatile PDMS), the polydimethylsiloxanes comprising alkyl or alkoxy groups, during and / or at the end of the silicone chain, groups each having from 2 to 24 carbon atoms;

Preferably, the non-volatile oil may be present in a content ranging from 0.1 to 60% by weight, in particular ranging from 0.5 to 50% by weight, and in particular ranging from 1 to 40% by weight, relative to the total weight of the composition.

In addition to the oils described above, the fatty phase may also comprise at least one fatty substance which is not liquid at ambient temperature (25 ° C.) and at atmospheric pressure, called solid fatty substance, chosen from waxes and pasty fatty substances. . Strong qras body

Preferably, the composition according to the invention may comprise in addition to the pasty fatty substance comprises at least one additional solid fat at 25 ° C. and at atmospheric pressure, chosen from waxes.

Waxes:

According to a preferred embodiment, the composition according to the invention comprises at least one wax. The wax considered in the context of the present invention is generally a lipophilic compound, solid at room temperature (25 ° C.), with reversible solid / liquid state change, having a melting point greater than or equal to 30 ° C. ° C can go up to 200 ° C and in particular up to 120 ° C. In particular, the waxes that are suitable for the invention may have a melting point greater than or equal to 45 ° C., and in particular greater than or equal to 55 ° C.

The waxes that may be used in the compositions according to the invention are chosen from waxes which are solid at room temperature (25 ° C.) of animal, vegetable, mineral or synthetic origin, and mixtures thereof. Illustrative waxes suitable for the invention include hydrocarbon waxes such as beeswax, lanolin wax, and Chinese insect wax, rice bran wax, Carnauba wax Candellila wax, Ouricury wax, Alfa wax 50, berry wax, shellac wax, Japanese wax and sumac wax; montan wax, orange and lemon waxes, microcrystalline waxes, paraffins and ozokerite; polyethylene waxes, waxes obtained by Fisher-Tropsch synthesis and waxy copolymers and their esters. There may also be mentioned waxes obtained by catalytic hydrogenation of animal or vegetable oils having linear or branched C8-C32 fatty chains. Among these, 3325 may especially be mentioned isomérisée jojoba oil such as trans isomerized partially hydrogenated jojoba oil manufactured or marketed by Desert Whale under the trade reference Iso-Jojoba-50®, the hydrogenated sunflower oil, hydrogenated castor oil, hydrogenated coconut oil, hydrogenated lanolin oil, and di- (1,1,1-trimethylolpropane) tetrastearate sold under the name Hest 2T- 4S® by the company HETERENE. Mention may also be made of silicone waxes (C30-45 ALKYL DIMETHICONE) and fluorinated waxes. It is also possible to use the waxes obtained by hydrogenation of castor oil esterified with cetyl alcohol sold under the names Phytowax Ricin 16L64® and 22L73® by the company SOPHIM. Such waxes are described in application FR-A-2792190. As the wax, a C20-C40 alkyl (hydroxystearyloxy) stearate (the alkyl group comprising from 20 to 40 carbon atoms), alone or in admixture, can be used.

Such a wax is especially sold under the names "Kester Wax K 82 P®", "Hydroxypolyester K 82 P®" and "Kester Wax K 80 P®" by the company Koster Keunen. As micro-waxes that can be used in the compositions according to the invention, mention may be made in particular of carnauba micro-waxes such as that marketed under the name MicroCare 350® by the company MICRO POWDERS, and synthetic wax micro-waxes such as that sold under the name MicroEase 114S® by MICRO POWDERS, micro waxes consisting of a mixture of carnauba wax and polyethylene wax such as those marketed under the names of Micro Care 300® and 310® by the company MICRO POWDERS, micro waxes consisting of a mixture of carnauba wax and synthetic wax such as that sold under the name Micro Care 325® by the company Micro Powders, polyethylene micro-waxes such as those sold under the names of Micropoly 200®, 220®, 220L® and 250S® by the company MICRO POWDERS and the polytetrafluoro micro waxes thylène such as those sold under the names Microslip 519® and 519 L® by Micro Powders. The composition according to the invention may comprise a wax content ranging from 0.1 to 30% by weight relative to the total weight of the composition, in particular it may contain from 0.5 to 20% by weight, more particularly from 1 to 15%.

Additional Film-forming Polymer The composition may comprise, in addition to the copolymer described above, an additional polymer such as a film-forming polymer. According to the present invention, the term "film-forming polymer" means a polymer capable of forming on its own or in the presence of an auxiliary film-forming agent, a continuous deposit on a support, in particular on keratin materials. Among the film-forming polymers that can be used in the composition of the present invention, mention may be made of synthetic polymers, of free radical type or of polycondensate type, polymers of natural origin, and mixtures thereof. As film-forming polymer, there may be mentioned in particular acrylic polymers, polyurethanes, polyesters, polyamides, polyureas, cellulose polymers such as nitrocellulose. The polymer may be associated with one or more auxiliary film-forming agents. Such a film-forming agent may be chosen from all the compounds known to those skilled in the art as being capable of fulfilling the desired function, and in particular be chosen from plasticizers and coalescing agents.

Lipophilic Gelling Agents According to one embodiment, the composition according to the invention may comprise at least one gelling agent. The gelling agents that may be used in the compositions according to the invention may be organic or inorganic, polymeric or molecular lipophilic gelling agents.

As inorganic lipophilic gelling agents, there may be mentioned optionally modified clays, such as hectorites modified with a C 10 -C 22 ammonium chloride, such as hectorite modified with di-stearyl dimethyl ammonium chloride such as, for example that marketed under the name Bentone 38V® by the company ELEMENTIS. It is also possible to mention the optionally hydrophobic fumed silica surface with a particle size of less than 1 μm. It is indeed possible to chemically modify the surface of the silica, by chemical reaction generating a decrease in the number of silanol groups present on the surface of the silica. In particular, it is possible to substitute silanol groups with hydrophobic groups: a hydrophobic silica is then obtained. The hydrophobic groups may be: trimethylsiloxyl groups, which are especially obtained by treatment of fumed silica in the presence of hexamethyldisilazane. Silicas thus treated are called "Silica silylate" according to the CTFA (8th edition, 2000). They are, for example, sold under the references Aerosil R812® by the company Degussa, CAB-O-SIL TS-530® by the company Cabot, dimethylsilyloxyl or polydimethylsiloxane groups, which are especially obtained by treatment of fumed silica in the presence of polydimethylsiloxane. or dimethyldichlorosilane. Silicas thus treated are called "Silica dimethyl silylate" according to the CTFA (8th edition, 2000). They are for example marketed under the references Aerosil R972®, and Aerosil R974® by the company DEGUSSA, CAB-OSIL TS-610® and CAB-O-SIL TS-720® by CABOT.

Among the lipophilic gelling agents that can be used in the compositions according to the invention, mention may also be made of dextrin and fatty acid esters, such as dextrin palmitates, in particular such as those sold under the names Rheopearl TL® or Rheopearl KL. ® by the company CHIBA FLOUR.

It is also possible to use silicone polyamides of the polyorganosiloxane type such as those described in US-A-5,874,069, US-A-5,919,441, US-A-6,051,216 and US-A-5,981,680. These silicone polymers may belong to the following two families: polyorganosiloxanes comprising at least two groups capable of establishing hydrogen interactions, these two groups being located in the polymer chain, and / or polyorganosiloxanes comprising at least two groups capable of to establish hydrogen interactions, these two groups being located on grafts or branches.

Charges: The composition according to the invention may comprise at least one filler. For the purposes of the present invention, the term "filler" means solid particles of all forms, which are in an insoluble form and dispersed in the medium of the composition, even at temperatures up to the melting point of all the bodies. fat of the composition.

Generally, the fillers used according to the invention are colorless or white, ie non-pigmentary, that is to say they are not used to impart a particular color or hue to the composition according to the invention, even if their use can inherently lead to such a result. These fillers serve in particular to modify the rheology or the texture of the composition.

As such, they are, in this respect, distinct from nacres, organic pigment materials such as, for example, carbon black, D & C type pigments, and lacquers based on cochineal carmine, barium, strontium, calcium, aluminum. and inorganic pigment materials such as, for example, titanium dioxide, zirconium or cerium oxides, as well as iron oxides (black, yellow or red) or chromium, manganese violet, ultramarine blue, hydrate chromium and ferric blue, which are used to provide a hue and color effect to the compositions incorporating them. Such compounds are not covered, for the purposes of the invention, by the definition of fillers which therefore cover non-pigmentary fillers that may be organic or inorganic. The non-pigmentary fillers used in the compositions according to the present invention may be of lamellar, globular, spherical, fiber-like, or any other form intermediate between these defined forms.

The size of the particles, namely their particle size, is chosen so as to ensure good dispersion of the fillers in the composition according to the invention. The particle size of the particles may be distributed in the range from 5 μm to 10 nm, in particular from 10 μm to 10 nm. The fillers according to the invention may or may not be superficially coated, in particular surface-treated with silicones, amino acids, fluorinated derivatives or any other substance which promotes dispersion and compatibility of the filler in the composition.

Mineral Charts For the purposes of the present invention, the terms "mineral" and "inorganic" are used interchangeably. Among the non-pigmentary inorganic fillers that can be used in the compositions according to the invention, mention may be made of talc, mica, silica, perlite, which is especially commercially available from WORLD MINERALS EUROPE under the trade name Perlite P1430 and Perlite P2550. or Perlite P204, kaolin, precipitated calcium carbonate, magnesium carbonate and hydrogen carbonate, hydroxyapatite, boron nitride, hollow silica microspheres (Silica Beads® from Maprecos), glass microcapsules or ceramic, and mixtures thereof. According to one embodiment, the cosmetic composition according to the invention comprises at least one non-pigmentary inorganic filler selected from the group comprising kaolin, talc, silica, perlite, clay and mixtures thereof.

Organic fillers Among the organic fillers, mention may be made of polyamide powders (Nylon® Orgasol® from Atochem), polyalanine and polyethylene, lauroyl-lysine, starch, tetrafluoroethylene polymer powders (Teflon® ), hollow polymer microspheres such as those of polyvinylidene chloride / acrylonitrile such as Expancel® (Nobel Industrie), acrylic acid copolymer (such as polytrap (Dow Corning)), acrylate copolymers, PMMA, 12-hydroxystearic acid oligomer stearate and silicone resin microspheres (Toshiba Tospearls®, for example), magnesium carbonate and hydrogen carbonate, metal soaps derived from organic carboxylic acids having 8 to 22 carbon atoms, preferably 12 to 18 carbon atoms, for example zinc, magnesium or lithium stearate, zinc laurate, magnesium myristate, and mixtures thereof.

For the purpose of the present invention, the organic fillers are distinct from the pigments. It may also be particles comprising a copolymer, said copolymer comprising trimethylol hexyl lactone. In particular, it may be a hexamethylene diisocyanate / trimethylol hexyllactone copolymer. Such particles are in particular commercially available, for example under the name PLASTIC POWDER D-400® or PLASTIC POWDER D-800® from the company TOSHIKI.

According to one embodiment, a composition of the invention may comprise at least one filler selected from talc, silica, starch, clay, kaolin, perlite, and mixtures thereof.

One or more dispersing agents may be optionally used to protect the dispersed fillers or particles against agglomeration or flocculation. They can be added independently of solid charges or particles or as a colloidal dispersion of particles. The dispersant concentration is chosen so as to obtain a satisfactory dispersion of the solid particles (without flocculation). This dispersing agent may be a surfactant, an oligomer, a polymer or a mixture of several of them, bearing one or more functionalities having a strong affinity for the surface of the particles to be dispersed. In particular, the polyhydroxy-12-stearic acid esters, such as poly (12-hydroxystearic acid) stearate, having a molecular weight of about 750 g / mole, such as that sold under the name Solsperse 21,000, are used. ® by the company Avecia, esters of polyhydroxy-12-stearic acid with polyols such as glycerol, diglycerine, such as polyglyceryl-2 dipolyhydroxystearate (CTFA name) sold under the reference Dehymuls PGPH® by the company HENKEL ( or poly (12-hydroxystearate) diglycerol), or else poly (12-hydroxystearic acid) such as that sold under the reference Arlacel P100 by Uniqema and their mixtures. As another dispersant that may be used in the composition of the invention, there may be mentioned quaternary ammonium derivatives of polycondensed fatty acids, such as Solsperse 17000® sold by the company Avecia, poly dimethylsiloxane / oxypropylene mixtures such as those sold by the company Dow Corning under the references DC2-5185, DC2-5225 C.

Additional Usual Cosmetic Ingredients The composition according to the invention may furthermore comprise any usual cosmetic ingredient that may be chosen in particular from film-forming polymers, antioxidants, perfumes, preservatives, neutralizers, surfactants, sunscreens, vitamins, moisturizers, self-tanning compounds, anti-wrinkle active agents, emollients, hydrophilic or lipophilic active agents, anti-free radical agents, deodorants, sequestering agents, film-forming agents, semi-crystalline polymers and mixtures thereof.

Of course, those skilled in the art will take care to choose any additional ingredients and / or their quantity so that the advantageous properties of the composition according to the invention are not or substantially not impaired by the addition envisaged.

The compositions according to the invention may be in any acceptable and customary form for a cosmetic composition. They can therefore be in the form of a suspension, a dispersion including oil in water with vesicles; an organic or oily solution optionally thickened or even gelled; an oil-in-water, water-in-oil, or multiple emulsion; a gel or a mousse; an oily or emulsified gel; a dispersion of vesicles, in particular lipids; a biphase or multiphase lotion; a spray; a lotion, a cream, an ointment, a soft paste, an ointment, a solid cast or molded and especially stick or cup, or compacted solid.

Those skilled in the art may choose the appropriate dosage form, as well as its method of preparation, on the basis of its general knowledge, taking into account, on the one hand, the nature of the constituents used, in particular their solubility in the support, and on the other hand, of the application envisaged for the composition.

Preferably, the composition according to the invention comprises less than 3%, or better, less than 1% water by weight relative to the total weight of the composition. More preferably the composition is completely anhydrous. By anhydrous is meant in particular that the water is preferably not deliberately added to the composition but may be present in trace form in the various compounds used in the composition. According to a preferred embodiment, the composition according to the invention is a lipstick.

According to a preferred embodiment, the composition according to the invention is in a linear form at 25 ° C., such as a gloss for the lips. According to another embodiment, the composition is in solid form at 25 ° C. In the case of a lipstick, it can act as a lipstick stick or a lipstick poured cup for example. By "solid" is meant a composition whose hardness measured according to the previous protocol is greater than or equal to 30 Nm- 'at the temperature of 20 ° C and at atmospheric pressure (760 mm Hg).

Protocol for Measuring Hardness: The hardness of the composition is measured according to the following protocol: The lipstick stick is stored at 20 ° C. for 24 hours before measuring the hardness. The hardness can be measured at 20 ° C. by the so-called "butter-cutting thread" method, which consists in transversely cutting a stick of product, preferably cylindrical of revolution, with the aid of a rigid tungsten wire. diameter 250 μm by moving the wire relatively to the stick at a speed of 100 mm / min. The hardness of the samples of compositions of the invention, expressed in Nm-1, is measured by means of a DFGS2 dynamometer marketed by INDELCOCHATILLON. The measurement is repeated three times and averaged. The average of the three values read using the dynamometer mentioned above, denoted Y, is given in grams. This average is converted to Newton and divided by L which represents the highest dimension traversed by the wire. In the case of a cylindrical stick, L is equal to the diameter (in meters). The hardness is converted to Nm 2 by the equation below: (Y x 10-3 x 9.8) / L For a measurement at a different temperature, the stick is kept at this new temperature for 24 hours before the measurement.

The compositions according to the invention can be used for the care or makeup of keratin materials such as the skin, the eyelashes, the eyebrows, the nails, the lips, and more particularly for the makeup of the lips, eyelashes and / or face.

They can therefore be in the form of a care product and / or makeup of the skin of the body or face, lips, eyelashes, eyebrows, or nails; a suntan or self-tanning product; they are advantageously in the form of a make-up composition, in particular mascara, eyeliner, lipstick, lip gloss, blush, eyeliner, foundation, nail varnish. nails or nail care.

The subject of the invention is also a process for the cosmetic treatment of keratin materials, in particular the skin of the body or of the face, the lips, the nails and / or the eyelashes, comprising the application to said materials of a cosmetic composition such as than previously defined. This process according to the invention makes it possible in particular to care for or make up said keratin materials, in particular the lips and / or the nails, by application of a composition, in particular lipstick, lip gloss, nail care or nail polish according to the invention.

The invention is illustrated in more detail in the following exemplary embodiments. EXAMPLE 1 to 3: Liquid lipsticks The following liquid lipstick compositions have been prepared: Compound Composition 1 Composition Composition according to the invention 2 according to 3 comparative (% by weight) the invention (% (wt.%) by weight) Supramolecular compound 75 75 75 prepared from JARCOL 24 (55.6% in isodode) (Supramolecular Compound No. 12 prepared below) before) GANEX V 220 (Pyrol-I-vinyl - done / EICOSENE copolymer marketed by ISP) Bis-diglyceryl polyacyladiparate-2 (SOFTISAN 649 from Sasol) SYNTHETIC polyethylene - - 10 (PF 41 C) (Performa V 343 polymer®, from New Phase Technologies) ISODODECANE 10 10 10 RED7 (UNIPUREREDLC 5 5 3079 OR from LCW (SENSIENT) Total: 100 100 100 Preparation Protocol: Firstly, the pigments are milled using a grinding machine. cylinder in part of the oily phase. Fat-soluble ingredients are then mixed at a temperature of the order of 50 ° C. (higher than the melting temperature of the solid fatty substances (pasty opu wax) present in the composition) with Rayneri stirring. The ground material is then added to the mixture and stirred to homogenize well. Then allowed to cool to room temperature and the juice is then packaged in a boil with an applicator.

After application to the lips, compositions 1 and 2 according to the invention form a non-tacky, glossy and non-transferable deposit immediately after application and 1 hour after application.

On the other hand, with comparative composition 3, the composition is inhomogeneous and is out of phase. We do not form a homogeneous deposit on the lips. 395

Claims (20)

REVENDICATIONS1. Cosmetic make-up and / or skincare composition of keratin materials containing, in a cosmetically acceptable medium, (i) a supramolecular compound obtainable by reaction between: at least one oil bearing at least one selected nucleophilic reactive function among OH and NH 2, and - at least one linking group capable of establishing hydrogen bonds with one or more partner joining groups, each pairing of a linking group involving at least 3 hydrogen bonds, said group of junction carrying at least one isocyanate or imidazole reactive functional group capable of reacting with the reactive function carried by the oil, said joining group also comprising at least one unit of formula (I) or (II): ## STR2 ## Wherein R1 and R3, which may be identical or different, represent a divalent carbon radical chosen from (i) C1-C32 linear or branched alkyl group, (ii) C4-C16 cycloalkyl group and (iii) C4-C16 aryl group; optionally comprising 1 to 8 heteroatoms selected from O, N, S, F, Si and P; and / or optionally substituted with an ester, amide or a C1-C12 alkyl radical; or a mixture of these groups; R2 represents a hydrogen atom or a linear, branched or cyclic, saturated or unsaturated, optionally aromatic, hydrocarbon radical, in C1-C32, which may comprise one or more heteroatoms chosen from O, N, S, F, Si and P; (ii) at least pasty polar fatty substance. 2. Composition according to claim 1, wherein the oil carrying the reactive function is chosen from, alone or in mixture: (i) fatty alcohols comprising 6 to 50 carbon atoms, linear, branched or cyclic, saturated or unsaturated comprising 1 or more OH; optionally comprising one or more NH2; (ii) esters and ethers bearing at least one free OH group, and in particular esters and partial polyol ethers, and hydroxylated carboxylic acid esters; (iii) natural, natural modified, vegetable, hydroxylated oils. 3. Composition according to one of the preceding claims, wherein the oil carrying the reactive function is selected from, alone or in mixture: - linear or branched monoalcohols C6-050, especially C6-C32, in particular C8 -C28, saturated or unsaturated, and in particular isostearyl alcohol, cetyl alcohol, oleic alcohol, oleyl alcohol, isopalmitoyl alcohol, 2-butyl octanol, 2-hexyl decanol, octyl -2 decanol, 2-octyldodecanol, 2-octyltetradecanol, 2-decyltetradecanol, 2-dodecyl hexadecanol; linear or branched C 6 -C 50, especially C 6 -C 40, in particular C 8 -C 45 C 38 diols, which are saturated or unsaturated, and in particular branched C 32 -C 36; linear or branched triols of C 6 -C 50, especially C 6 -C 32, in particular C 8 -C 28, saturated or unsaturated, and especially phytantriol; the partial esters of pentaerythritol, and in particular pentaerythrityl adipate, pentaerythrityl caprate, pentaerythrityl succinate, pentaerythrityl tetraisonanoate, pentaerythrityl triisononanoate, pentaerythrityl tetraisostearate, pentaerythrityl triisostearate, tetradecyltetradecanoate, pentaerythrityl, pentaerythrityl tetraethyl hexanoate, pentaerythrityl tetraoctyl dodecanoate; dipentaerythritol diesters, triesters, tetraesters or pentaesters, and especially dipentaerythrityl pentaisononanoate, dipentaerythrityl pentaisostearate, dipentaerythrityl tetraisostearate, di pentaerythrityl tri (polyhydroxystearate); trimethylolpropane mono- and di-esters such as trimethylolpropane monoisostearate, tri-methylolpropane di-isostearate, trimethylolpropane monoethyl-2-hexylate, trimethylolpropane diethyl-2-hexylate; mono-, di- and tri-esters of di-trimethylolpropane such as di-trimethylolpropane diisostearate, di-trimethylolpropane triisostearate, di-trimethylolpropane tri-ethyl hexanoate; the mono-esters or partial polyesters of glycerol or polyglycerols, and especially: glycerol di-isostearate, glycerol di-isononanoate, polyglycerol-2 mono-, di- and tri-esters; for example with isostearic acid, 2-ethyl hexyl acid and / or isononanoic acid; and in particular polyglyceryl-2-isostearate; polyglyceryl-2-diisostearate; polyglyceryl-2 triisostearate; polyglyceryl-2-nonaisostearate; polyglyceryl-2-nonanoate; mono-, di-, tri- or tetra-esters of polyglycerol-3; for example with either isostearic acid, 2-ethyl hexyl acid and / or isononanoic acid; and especially polyglyceryl-3-isostearate, polyglyceryl-3-diisostearate; polyglyceryl-3 triisostearate; polyglyceryl-3-nonaisostearate; polyglyceryl-3-nonanoate; partial esters of polyglycerol-10 and in particular polyglyceryl-10 nonaisostearate; polyglyceryl-10-nonanoate; polyglyceryl-10-isostearate, polyglyceryl-10-diisostearate, polyglyceryl-10 triisostearate; propylene glycol monoesters such as propylene glycol monoisostearate, propylene glycol neopentanoate, propylene glycol monooctanoate; dimer-diol monoesters such as isostearyl dimer dilinoleate and octyl dodecyl dimer dilinoleate; glycerol ethers, such as polyglyceryl-2-oleyl ether, polyglyceryl-3-cetyl ether, polyglyceryl-3-decyltetradecyl ether and polyglyceryl-2 stearyl; esters between hydroxylated mono-, di- or tri-carboxylic acid and monoalcohols, and in particular: esters, in particular monoesters, of 12-hydroxystearic acid; such as octyl hydroxystearate and octyl-2-dodecyl hydroxystearate; mention may also be made of the corresponding oligomeric polyhydroxystearates, in particular having a degree of polymerization of 1 to 10, having at least one residual OH; esters of lactic acid, and in particular C4-40 alkyl lactates, such as 2-ethylhexyl lactate, diisostearyl lactate, isostearyl lactate, isononyl lactate, lactate, 2-octyldodecyl; malic acid esters, and in particular C4-40 alkyl malates, such as 2-diethyl hexyl malate, diisostearyl malate, 2-dioctyl dodecyl malate; esters of citric acid, and in particular C4-40 alkyl citrates, such as triisostearyl citrate, triisocetyl citrate and tri-isoarachidyl citrate. triglycerine esters bearing one or more OH, castor oil, hydrogenated or not, and its derivatives, in particular derived from the transesterification of castor oil; modified epoxidized oils, the modification consisting of opening the epoxy function to obtain a diol, and especially hydroxylated modified soybean oil; hydroxylated soybean oils (directly hydroxylated or first epoxidized). 4. Composition according to one of the preceding claims, wherein the oil is a brilliant oil, that is to say having a refractive index greater than or equal to 1.46 at 25 ° C. 5. Composition according to one of the preceding claims, in which the oil has a molar mass (Mw) of between 150 and 6000, in particular between 170 and 4000, and even between 180 and 2000, preferably between 200 and 1500, and even better between 220 and 800 g / mol. 6. Composition according to claim 1, wherein the oil bearing the reactive function is chosen from: - fatty alcohols comprising 6 to 50 carbon atoms, linear, branched or cyclic, saturated or unsaturated, comprising 1 or more OH; optionally comprising one or more NH 2, such as linear or branched C 6 -C 50, especially C 6 -C 32, in particular C 8 -C 28, monohydric, saturated or unsaturated alcohols, and especially isostearyl alcohol, cetyl alcohol, oleic alcohol, oleyl alcohol, isopalmitoyl alcohol, butyl-2-octanol, 2-hexyl decanol, 2-octyl decanol, 2-octyldodecanol, 2-octyltetradecanol, decylbenzoyl, 2 tetradecanol, 2-dodecyl-hexadecanol, - esters of dicarboxylic acid hydroxylated with a monoalcohol, and in particular of malic acid, and in particular C4-40 alkyl malates, such as 2-diethyl hexyl malate; , diisostearyl malate, dioctyl-2-dodecyl malate. 7. Composition according to one of the preceding claims, wherein in the joining group, the radical R1 represents: a divalent alkylene group, linear or branched, C 2 -C 12, in particular a 1,2-ethylene group, 1 , 6-hexylene, 1,4-butylene, 1,6- (2,4,4-trimethylhexylene), 1,4- (4-methylpentylene), 1,5- (5-methylhexylene), 1,6- ( 6-methylheptylene), 1,5- (2,2,5-trimethylhexylene), 1,7- (3,7-dimethyloctylene). a divalent C 4 -C 12 cycloalkylene or arylene group, especially chosen from the following radicals: isophorone, tolylene, 2-methyl-1,3-phenylene, 4-methyl-1,3-phenylene; 4,4'-méthylènebiscyclohexylène; 4,4-bisphénylèneméthylène; or structure: * CH * 8. Composition according to one of the preceding claims, wherein, in the junction group, the radical R2 represents H, or else: - a C1-C32 alkyl group, in particular C1-C16, or even C1-C10; ; a C4-C12 cycloalkyl group; a C4-C12 aryl group; an aryl (C 4 -C 12) C 1 -C 18 alkyl group or a C 1 -C 4 alkoxy group; an arylalkoxy group, in particular a (C 1 -C 4) aryl alkoxy group; a C4-C12 heterocycle or a combination of these radicals, which may optionally be substituted by an amino, ester and / or hydroxyl function. 9. Composition according to one of the preceding claims, wherein, in the junction group, the radical R3 represents a divalent radical R R -3-OC (O) -NH-R '4 - in which R' 3 and R ' 4, which may be identical or different, represent a divalent carbon radical chosen from a linear or branched C1-C32 alkyl group or a C4-C16 cycloalkyl group or a C4-C16 aryl group; or their mixture. 10. Composition according to one of the preceding claims, wherein in the junction group, (a) in the formula (I), there is: - R, = -isophorone- and R2 = methyl, - R, = - (CH2) 6- and R2 = methyl, - R, = - (CH2) 6- and R2 = isopropyl, or - R4 = 4,4'-methylenebiscyclohexylene and R2 = methyl, or (b) in the formula (II), R1 represents the radical -isophorone-, R2 = methyl and R3 = - (CH2) 2OOO-NH-isophorone-. 11. Composition according to one of the preceding claims, in which the linking group has the formula: embedded image or of formula: ## STR2 ## in which wherein R1, R2 and R3 are as defined in any one of the preceding claims. 12. Composition according to one of the preceding claims, wherein the junction group is selected from the following groups: ## STR1 ## HL / CH3 O \ N ~ \ N ~ \ N ~~~ HH x ONON NCO O OCN XHH 13. Composition according to one of the preceding claims, in which the supramolecular compounds are chosen from those having the following structures: ## STR2 ## isostearyl alcohol and isostearyl ammonium nitrate OII 0 0 0 HH 1 isostearyl X 0 0 0 OO ~ NO 0ùisostearyl isostearyl OO isostearyl 10HO Nid NNN) N \ O .KHH 14. Composition according to one of the preceding claims, wherein the number-average molecular mass (Mn) of the supramolecular compound is between 180 to 8000, preferably 200 to 6000, or even 300 to 4000, and even more preferably 400 to 3000, preferably 500 to 1500. 10 15. Composition according to one of the preceding claims, wherein the amount of supramolecular compound present in the composition is between 5% and 95% by weight, preferably between 10% and 95% by weight, and more preferably between 20% and 95% by weight. % and 90% by weight relative to the total weight of the composition. 15 16. Composition according to one of the preceding claims, characterized in that said pasty polar fatty substance is chosen from: lanolin and its derivatives, polyol ethers chosen from pentaerythritol and polyalkylene glycol ethers, ethers fatty alcohol and sugar, and mixtures thereof, vinyl polymers, in particular those chosen from: linear or branched oligomers, homo or copolymers of alkyl (meth) acrylates preferably having a C8-C30 alkyl group; Homo- and copolymeric oligomers of vinyl esters having C 8 -C 30 alkyl groups; homo- and copolymer oligomers of vinyl ethers having C 8 -C 30 alkyl groups; liposoluble polyethers resulting from the polyetherification between one or more diols C2-C100, in particular copolymers of ethylene oxide and / or propylene oxide with C6-C30.5 long chain alkylene oxides; is among: homo- and copolymer oligomers of vinyl ethers having alkyl groups, esters of an oligomeric glycerol, in particular condensates of adipic acid and of glycerol, for which part of the hydroxyl groups of the glycerols have reacted with a mixture of fatty acids, • arachidyl propionate, • phytosterol esters, • triglycerides of fatty acids and their derivatives, • pentaerythritol esters, • non-crosslinked polyesters resulting from the polycondensation between a dicarboxylic acid or a linear or branched C 4 -C 50 polycarboxylic acid and a C2-050 diol or polyol; • aliphatic ester esters resulting from the esterification of an aliphatic hydroxycarboxylic acid ester with an aliphatic carboxylic acid, aliphatic hydroxy carboxylic acid ester may be chosen from: a) partial or total esters of linear monohydroxylated aliphatic monocarboxylic acids, its turés; b) partial or total esters of unsaturated monohydroxylated aliphatic monocarboxylic acids; c) partial or total esters of saturated monohydroxylated aliphatic polycarboxylic acids; d) partial or total esters of saturated polyhydroxylated aliphatic polycarboxylic acids; e) partial or total esters of C 2 to C 16 aliphatic polyols reacted with a mono- or polyhydroxylated aliphatic mono- or polycarboxylic acid, and mixtures thereof, • esters of diol dimer and diacid dimer, where appropriate, esterified on their function (s) alcohol (s) or acid (s) free (s) by acidic radicals or alcohols, especially dimer dilinoleate esters, • esters of hydrogenated rosinate, such as dimers dilinoleyl hydrogenated rosinate, - and their mixtures. 17. - The composition according to one of the preceding claims, characterized in that the pasty fatty substance is present in a total content ranging from 0.1 to 80%, better 0.5 to 60%, better 1 to 30% and better still 1 to 20% by weight relative to the total weight of the composition. 18. Composition according to one of the preceding claims, characterized in that it comprises at least one dyestuff, preferably chosen from organic or inorganic, liposoluble or water-soluble dyestuffs, materials with specific optical effect and mixtures thereof. 19. Composition according to one of the preceding claims, in the form of a care composition and / or makeup of the skin of the body or face, lips, eyelashes, eyebrows, or nails; a solar or self-tanning product. 20. Process for the cosmetic treatment of keratinous substances, in particular the skin of the body or of the face, lips, nails, and / or eyelashes, comprising the application to said materials of a cosmetic composition as defined according to US Pat. any of claims 1 to 19.