WO2011147696A1 - Composition cosmétique comprenant une huile et un polymère, qui comportent chacun un groupe de liaison générant une liaison hydrogène, et procédé de traitement cosmétique - Google Patents

Composition cosmétique comprenant une huile et un polymère, qui comportent chacun un groupe de liaison générant une liaison hydrogène, et procédé de traitement cosmétique Download PDF

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Publication number
WO2011147696A1
WO2011147696A1 PCT/EP2011/057783 EP2011057783W WO2011147696A1 WO 2011147696 A1 WO2011147696 A1 WO 2011147696A1 EP 2011057783 W EP2011057783 W EP 2011057783W WO 2011147696 A1 WO2011147696 A1 WO 2011147696A1
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group
oil
polymer
chosen
weight
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PCT/EP2011/057783
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English (en)
Inventor
Sandrine Chodorowski-Kimmes
Charlotte Feltin
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L'oreal
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Priority to CN201180036081.5A priority Critical patent/CN103391765B/zh
Priority to EP11719274.0A priority patent/EP2575751A1/fr
Priority to US13/700,021 priority patent/US20130136705A1/en
Publication of WO2011147696A1 publication Critical patent/WO2011147696A1/fr

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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/494—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
    • A61K8/4953—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom containing pyrimidine ring derivatives, e.g. minoxidil
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • A61K8/8194—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds; Compositions of derivatives of such polymers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q1/00—Make-up preparations; Body powders; Preparations for removing make-up
    • A61Q1/02—Preparations containing skin colorants, e.g. pigments
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q1/00—Make-up preparations; Body powders; Preparations for removing make-up
    • A61Q1/02—Preparations containing skin colorants, e.g. pigments
    • A61Q1/04—Preparations containing skin colorants, e.g. pigments for lips
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q1/00—Make-up preparations; Body powders; Preparations for removing make-up
    • A61Q1/02—Preparations containing skin colorants, e.g. pigments
    • A61Q1/08—Preparations containing skin colorants, e.g. pigments for cheeks, e.g. rouge
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q1/00—Make-up preparations; Body powders; Preparations for removing make-up
    • A61Q1/02—Preparations containing skin colorants, e.g. pigments
    • A61Q1/10—Preparations containing skin colorants, e.g. pigments for eyes, e.g. eyeliner, mascara

Definitions

  • Cosmetic composition comprising an oil and a polymer both bearing a hydrogen-bond-generating joining group, and cosmetic treatment process
  • the present invention relates to novel cosmetic compositions comprising a mixture of H-bond-generating (supramolecular) polymers and of H-bond-generating (su- pramolecular) oils, and to the use thereof in the cosmetics industry, in particular in the makeup field.
  • H-bond-generating upramolecular
  • H-bond-generating su- pramolecular oils
  • one or more polymers which are in fact dedicated to providing these properties of improved staying power over time is (are) commonly introduced into compositions of this type.
  • polyacrylates and latexes By way of illustration of these polymers, mention may in particular be mentioned of polyacrylates and latexes.
  • the abovementioned polymers which are advantageous in terms of staying power properties, are unfortunately capable of generating a feeling of discomfort, during application (difficult spreading, tackiness) and/or after application (tautness, mask effect), of the cosmetic product containing them.
  • Supramolecular polymers such as those described in applications EP 2189151 and FR 2938758 are, on the other hand, known for making it possible to obtain, on the skin, a deposit which is both comfortable and has good staying power properties.
  • the deposits formed using a galenical formulation incorporating such a supramolecular polymer may have insufficient mechanical strength (which can be reflected by staining of the clothes).
  • bringing them into contact with fatty substances for example a food oil in the case of a lipstick applied to the lips, can affect their integrity. Consequently, there remains a need to be free of these drawbacks with respect to supramolecular polymer-based galenical formulations.
  • compositions for which properties of gloss of the deposited film, after application to the keratin materials, are desired. Mention may, for example, be made of lipsticks or nail varnishes. In order to obtain such a result, it is possible to combine particular starting materials, in particular lanolins, with "glossy" oils.
  • oils of triglyceride type in the case in point castor oil, functionalized with isophorone diisocyanate (IPDI), as is described in US 5 707 612.
  • IPDI isophorone diisocyanate
  • Application EP2140858 has also proposed cosmetic compositions which make it possible to obtain a uniform, film-forming deposit on the substrate, said film allying gloss, gloss fastness and staying power of the composition, while at the same being relatively non-tacky.
  • the deposits obtained with these functionalized oils can be more or less tacky and exhibit a certain amount of fragility with respect to wear; moreover, it has been found that these deposits exhibit, in addition to their tacky nature, a not insignificant sensitivity to fatty substances, in particular over time.
  • polymeric or nonpolymeric materials capable of generating deposits which exhibit good resistance, and therefore a certain amount of staying power, with re- spect to external attacks, in particular to "attacks" by fatty substances, such as, for example, by food oil or sebum, while at the same time preferably retaining their gloss, are sought in particular in the makeup field.
  • the objective of the present invention is to overcome these drawbacks and to pro- pose a cosmetic composition which makes it possible to obtain good cosmetic properties such as good adhesion to the support (skin or hair), and therefore good staying power of the composition, optionally good gloss, while at the same time also resulting in a deposit which is not very tacky or not at all tacky, and particularly resistant to external attacks by fatty substances (oil, meal, sebum) and also to rubbing, hence the deposit being worn away to a lesser extent.
  • a subject of the present invention is a cosmetic composition
  • a cosmetically acceptable medium a) at least one supramolecular oil (compound A) (also referred to as supramolecu- lar compound derived from an oil) which can be obtained by reaction between:
  • an oil bearing at least one nudeophilic reactive function in particular chosen from OH and NH 2 , and
  • joining group capable of establishing hydrogen bonds with one or more partner joining groups, each pairing of a joining group involving at least 4 hydrogen bonds, said joining group bearing at least one reactive function capable of reacting with the reactive function borne by the oil, in particular chosen from isocyanate, acid and imidazole, said joining group also comprising at least one unit of formula (la) or (lb):
  • R1 and R3 which may be identical or different, represent a divalent carbon- based radical chosen from (i) a linear or branched C1-C32 alkyl group, (ii) a C 4 -Ci6 cycloalkyl group and (iii) a C 4 -Ci6 aryl group; said groups optionally comprising 1 to 8 heteroatoms chosen from O, N, S, F, Si and P; and/or being optionally substituted with an ester or amide function or with a C1-C12 alkyl radical; or a mixture of these groups;
  • R2 and R4 independently of one another, represent a hydrogen atom or a linear, branched or cyclic, saturated or unsaturated, optionally aromatic, C1-C32 carbon- based, in particular hydrocarbon-based (alkyl), radical which can comprise one or more heteroatoms chosen from O, N, S, F, Si and P; and b) at least one polyalkene-based supramolecular polymer which can result from the reaction, in particular from the condensation, of at least one polyalkene polymer functionalized with at least one reactive function, with at least one joining group functionalized with at least one reactive group capable of reacting with the reactive group(s) borne by the functionalized polyalkylene polymer, said joining group being capable of forming at least 3 H (hydrogen) bonds, preferably at least 4 H bonds, preferentially 4 H bonds.
  • compositions according to the invention thus comprise 2 supramolecular compounds:
  • first compound A also known as supramolecular oil which is obtained from an oil (preferably a nonpolymeric oil)
  • oil preferably a nonpolymeric oil
  • compound B which is a supramolecular polymer distinct from compound A.
  • compositions of which the comfort is improved are obtained; they make it possible to obtain a film which is not very tacky, and which may or may not be glossy, while at the same time also being resistant to fatty substances and to mechanical wear.
  • Supramolecular chemistry makes it possible, through the supramolecular interactions, to mix (polymeric or nonpolymeric) compounds of different chemical natures and to obtain original properties that are different from those of the compounds used before mixing.
  • the supramolecular polymers and the supramolecular oils used in the context of the invention are not necessarily compatible with one another and are not necessarily easily conveyed in the same range of customary cosmetic solvents, such as carbon-based oils, fatty alcohols, fatty or short esters, and most particularly in media comprising isododecane, sesam, isononyl isononanoate, octyldo- decanol and/or a C12-C15 alkyl benzoate.
  • customary cosmetic solvents such as carbon-based oils, fatty alcohols, fatty or short esters, and most particularly in media comprising isododecane, sesam, isononyl isononanoate, octyldo- decanol and/or a C12-C15 alkyl benzoate.
  • compositions according to the invention thus comprise a supramolecular compound (compound A also known as supramolecular) derived from an oil which can be referred to as "H-bond-generating oil" and which can be obtained by reaction between:
  • an oil bearing at least one nucleophilic reactive function in particular chosen from OH and NH 2 , and
  • joining group capable of establishing hydrogen bonds with one or more partner joining groups, each pairing of a joining group involving at least 4 hydrogen bonds, said joining group bearing at least one reactive function capable of reacting with the reactive function borne by the oil, in particular chosen from isocyanate, acid and imidazole, said joining group also comprising at least one unit of formula (la) or (lb):
  • R1 and R3 which may be identical or different, represent a divalent carbon- based radical chosen from (i) a linear or branched C1-C32 alkyl group, (ii) a C 4 -Ci6 cycloalkyl group and (iii) a C 4 -Ci6 aryl group; said groups optionally comprising 1 to 8 heteroatoms chosen from O, N, S, F, Si and P; and/or being optionally substi- tuted with an ester or amide function or with a C1-C12 alkyl radical; or a mixture of these groups;
  • R2 and R4 independently of one another, represent a hydrogen atom or a linear, branched or cyclic, saturated or unsaturated, optionally aromatic, C1-C32 carbon- based, in particular hydrocarbon-based (alkyl), radical which can comprise one or more heteroatoms chosen from O, N, S, F, Si and P.
  • the compounds A according to the invention thus comprise at least one part (HB) originating from the oil and at least one part (G) originating from the join- ing group, said part (G) comprising at least one unit of formula (la) or (lb).
  • said parts (HB) and (G) are connected via a covalent bond, and in particular can be connected via a covalent bond formed during the reaction between the OH and/or NH 2 reactive functions borne by the oil and the isocyanate functions borne by the joining group; or else between the NH 2 reactive functions borne by the oil and the isocyanate, acid or imidazole functions borne by the joining group.
  • the preferential obtaining of the compounds A according to the invention can therefore in particular be represented schematically by the chemical reaction between the following entities:
  • the oil which can be used to prepare the compound according to the invention which can preferably be represented schematically as (HB)-(OH) m (NH 2 ) n , is a fatty substance, or a mixture of fatty substances, which is non-crystalline at 25°C, preferably liquid at ambient temperature and at atmospheric pressure (25°C, 1 atm.), preferably apolar, or even preferably water-insoluble.
  • the oil which can be used to prepare the supramolecular compound according to the invention is nonpolymeric.
  • liquid is intended to mean that the viscosity of the compound is less than or equal to 2500 centipoises, at 1 10°C, 1 atm., measured with a Brookfield DV-I or Brookfield Cap 1000+ rheometer, those skilled in the art choosing the instrument suitable for measuring viscosity.
  • apolar is intended to mean a compound of which the HLB (hydrophilic- lipophilic balance) value is low, in particular less than or equal to 8, preferably less than or equal to 4, and even better still less than or equal to 2; preferentially, the HLB value should be sufficiently low to make it possible to obtain a supramolecular material which is not, or not too, hygroscopic.
  • HLB hydrophilic- lipophilic balance
  • insoluble is intended to mean that the fraction of oil which can dissolve in water, at 25°C, 1 atm, is less than 5% by weight (i.e. 5 g of oil in 100 ml of water), preferably less than 3%.
  • fatty substance is intended to mean, in particular but not exclusively, a hydrocarbon-based compound comprising one or more linear, cyclic or branched, saturated or unsaturated, alkyl chains containing at least 6 carbon atoms and able to comprise polar groups, for instance an acid group, a hydroxyl or a polyol, amine, amide, phosphoric acid, phosphate, ester, ether, urea, carbamate, thiol, thioether or thioester group, it being possible for this chain to contain up to 100 carbon atoms.
  • polar groups for instance an acid group, a hydroxyl or a polyol, amine, amide, phosphoric acid, phosphate, ester, ether, urea, carbamate, thiol, thioether or thioester group, it being possible for this chain to contain up to 100 carbon atoms.
  • the oil which can be used to prepare compound A according to the invention is a glossy oil, i.e. an oil having a refractive index of greater than or equal to 1 .46 at 25°C, in particular between 1 .46 and 1 .55 (the refractive index being defined relative to the D line of sodium, at 25°C).
  • the oil which can be used to prepare the compound according to the invention is a non-volatile oil.
  • non-volatile oil is intended to mean an oil capable of remaining on keratin materials, at ambient temperature and atmospheric pressure, for at least several hours, and in particular having a vapour pressure of less than 10 "3 mmHg (0.13 Pa).
  • the oil has a molar mass (Mw) of between 150 and 6000, in particular between 170 and 4000, or even between 180 and 2000, preferentially between 200 and 1500, and even better still between 220 and 800 g/mol.
  • Mw molar mass
  • the oil which can be used in the context of the present invention to prepare the supramolecular compound A used in the compositions according to the invention bears at least one reactive function capable of reacting with the reactive function borne by the joining group, in particular capable of reacting chemically with the isocyanate, acid or imidazole groups borne by the joining group; preferably, this function is an OH or NH 2 function.
  • the oil comprises only OH functions, in particular 1 to 3 OH functions, preferentially primary or secondary OH functions.
  • the oil according to the present invention is preferably a carbon-based, in particular hydrocarbon-based, oil which, in addition to the reactive function capable of reacting with the joining group, may comprise oxygen, nitrogen, sulphur and/or phosphorus atoms.
  • the oil is very preferentially chosen from cosmetically acceptable oils.
  • the oil which can be used in the context of the present invention to prepare the supramolecular compound A used in the compositions according to the invention may be chosen from: (i) linear, branched or cyclic, saturated or unsaturated, fatty alcohols comprising 6 to 50 carbon atoms and comprising one or more OH, optionally comprising one or more NH 2 .
  • C6-C50 especially C6-C32, in particular C8-C28, triols, and in particular phytantriol;
  • esters and ethers bearing at least one free OH group and in particular partial esters and ethers of a polyol, and hydroxylated carboxylic acid esters.
  • partial ester of a polyol is intended to mean the esters prepared by es- terification of a polyol with a carboxylic acid, which may be substituted or unsubsti- tuted, the reaction not being complete, i.e. not carried out on all the free OH groups of the polyol; in the end, the ester thus also comprises at least one free OH.
  • the carboxylic acid is a monoacid.
  • a mixture of carboxylic acids, in particular monocarboxylic acids, may also be used.
  • partial ether of a polyol is intended to mean the ethers prepared by etherification of a polyol, on itself or with at least one other alcohol, which is mono- or polyhydroxylated, preferably monoalcohol, the etherification reaction not being complete, i.e. not carried out on all the free OH groups of the polyol; in the end, the ether also comprises at least one free OH.
  • hydroxylated carboxylic acid ester is intended to mean the (mono and poly) esters prepared by reaction between a carboxylic acid bearing at least one OH function, and one or more (mono or poly) alcohols, preferably monoalcohol, it being possible for the reaction to be complete or partial (carried out on all or some of the free OH groups of the alcohol).
  • polyols which can be used to prepare the esters or ethers above, mention may be made of propylene glycol, glycerol, neopentyl glycol, trimethylolpro- pane, trimethylolethane, polyglycerols, and in particular polyglycerol-2, polyglyc- erol-3 and polyglycerol-10; erythritol, dipentaerythritol, pentaerythritol, bis(trimethylolpropane), phytantriol, sucrose, glucose, methylglucose, sorbitol, fructose, xylose, mannitol or glucosamine; and also diol dimmers, in particular obtained from fatty acid dimers, in particular branched aliphatic and/or alicyclic C32- C38 and in particular C36 diols, such as those defined in the article Hofer et al. European Coating Journal (March 2000), pages 26
  • carboxylic acids that can be used to prepare the esters or ethers above, mention may be made of linear or branched, saturated or unsaturated monoacids containing 6 to 50 carbon atoms and diacids containing from 3 to 12 carbon atoms, among which mention may be made of octyldodecanoic acid, hexyldecanoic acid, ethylhexanoic 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 and decanoic acid, and mixtures thereof.
  • octyldodecanoic acid hexyldecanoic acid
  • ethylhexanoic acid isostearic acid, nonanoic acid
  • hydroxylated carboxylic acids that can be used to prepare the esters or ethers above, mention may be made of monohydroxylated or polyhydroxylated acids, preferably monohydroxylated acids, containing, for example, 4 to 28 carbon atoms, and in particular 12-hydroxystearic acid, ricinoleic acid, malic acid, lactic acid and citric acid, and mixtures thereof.
  • the oil which can be used in the present invention to prepare the su- pramolecular compound A may be chosen, alone or as a mixture, from:
  • pentaerythritol partial esters and in particular pentaerythrityl adipate, pentae- rythrityl caprate, pentaerythrityl succinate, pentaerythrityl tetraisononanoate, pentaerythrityl triisononanoate, pentaerythrityl tetraisostearate, pentaerythrityl tri- isostearate, pentaerythrityl 2-(tetradecyl)tetradecanoate, pentaerythrityl (tetra- ethyl)hexanoate and pentaerythrityl (tetraoctyl)dodecanoate;
  • dipentaerythritol diesters triesters, tetraesters or pentaesters, and in particular dipentaerythrityl pentaisononanoate, dipentaerythrityl pentaisostearate, dipentae- rythrityl tetraisostearate and dipentaerythrityl tris(polyhydroxystearate);
  • trimethylolpropane monoesters and diesters for instance trimethylolpropane monoisostearate, trimethylolpropane diisostearate, trimethylolpropane mono(2- ethylhexylate) and trimethylolpropane di(2-ethylhexylate);
  • polyglycerol-2 monoesters, diesters and triesters for example with isostearic acid, 2-ethylhexanoic acid and/or isononanoic acid; and in particular polyglyceryl-2 isostearate; polyglyceryl-2 diisostearate; polyglyceryl-2 triisostearate; polyglyceryl- 2 nonaisostearate; polyglyceryl-2 nonanoate;
  • polyglycerol-3 monoesters, diesters, triesters and tetraesters for example with either isostearic acid, 2-ethylhexanoic acid and/or isononanoic acid; and in particular polyglyceryl-3 isostearate, polyglyceryl-3 diisostearate; polyglyceryl-3 tri- isostearate; polyglyceryl-3 nonaisostearate; polyglyceryl-3 nonanoate;
  • polyglycerol-10 partial esters and in particular polyglyceryl-10 nonaisostearate; polyglyceryl-10 nonanoate; polyglyceryl-10 isostearate, polyglyceryl-10 diisostearate, polyglyceryl-10 triisostearate; - propylene glycol monoesters, for instance propylene glycol monoisostearate, propylene glycol neopentanoate, propylene glycol monooctanoate;
  • diol dinner monoesters for instance isostearyl dimer dilinoleate and octyldodecyl dimer dilinoleate;
  • - glycerol ethers such as polyglyceryl-2 oleyl ether, polyglyceryl-3 cetyl ether, po- lyglyceryl-3 decyl tetradecyl ether and polyglyceryl-2 stearyl ether;
  • esters in particular monoesters, of 12-hydroxystearic acid, such as octyl hydroxystearate and 2-octyldodecyl hydroxystearate; mention may also be made of the corresponding oligomeric polyhydroxystearates, in particular having a degree of polymerization of from 1 to 10, bearing at least one residual OH;
  • C 4 -C 4 o alkyl lactates such as 2-ethylhexyl lactate, diisostearyl lactate, isostearyl lactate, isononyl lactate or 2- octyldodecyl lactate;
  • C 4 - malic acid esters and in particular C 4 -C 4 o alkyl malates, such as 2-diethyl- hexyl malate, diisostearyl malate or 2-dioctyldodecyl malate;
  • C 4 - citric acid esters and in particular C 4 -C 4 o alkyl citrates, such as tri- isostearyl citrate, triisocetyl citrate and triisoarachidyl citrate;
  • - modified epoxidized oils the modification consisting in opening the epoxy function to obtain a diol, and in particular hydroxylated modified soybean oil; hydroxylated soybean oils (directly hydroxylated or epoxidized beforehand); and in particular the oils Agrol 2.0, Agrol 3.0 or Agrol 7.0 sold by BioBased Technologies, LLC; the oil Soyol R2-052 from the company Urethane Soy System; the Renuva oils sold by Dow Chemical; the BioH Polyol 210 and 500 oils sold by Cargill.
  • the oil which can be used to prepare the supramolecular compound A in the present invention is preferably chosen from:
  • esters between a hydroxylated monocarboxylic, dicarboxylic or tricarboxylic acid and monoalcohols and in particular:
  • esters in particular monoesters, of 12-hydroxystearic acid; such as octyl hydroxystearate and 2-octyldodecyl hydroxystearate; mention may also be made of the corresponding oligomeric polyhydroxystearates, in particular having a degree of polymerization of from 1 to 10, bearing at least one residual OH;
  • C 4 -C 4 o alkyl lactates such as 2-ethylhexyl lactate, diisostearyl lactate, isostearyl lactate, isononyl lactate or 2-octyldodecyl lactate;
  • C 4 - malic acid esters and in particular C 4 -C 4 o alkyl malates, such as 2-diethylhexyl malate, diisostearyl malate or 2-dioctyldodecyl malate;
  • C 4 - citric acid esters and in particular C 4 -C 4 o alkyl citrates, such as triisostearyl citrate, triisocetyl citrate and triisoarachidyl citrate;
  • fatty alcohols (i) may be:
  • C6-C50 saturated or unsaturated C6-C50, especially C6-C32, in particular C8-C28, monoalcohols, and in particular isostearyl alcohol, cetyl alcohol, oleyl alcohol, isopalmitoyl alcohol, 2-butyloctanol, 2-hexyldecanol, 2-octyldecanol, 2-octyldodecanol, 2-octyltetradecanol, 2-decyltetradecanol, 2-dodecylhexadecanol, and in particular the alcohols sold under the name Jarcol by the company Jarchem Industries, such as Jarcol 1-12, Jarcol 1-16, Jarcol I-20 and Jarcol I-24;
  • C6-C50 saturated or unsaturated C6-C50, especially C6-C32, in particular C8-C38, triols, and in particular phytantriol.
  • the oil which can be used to pre- pare the supramolecular compound A in the context of the present invention is preferably chosen from linear or branched, saturated or unsaturated, C6-C50, especially C6-C32, in particular C8-C28, monoalcohols, and in particular isostearyl alcohol, cetyl alcohol, oleyl alcohol, isopalmitoyl alcohol, 2-butyloctanol, 2-hexyldecanol, 2-octyldecanol, 2-octyldodecanol, 2-octyltetradecanol, 2-decyl- tetradecanol, 2-dodecylhexadecanol, and in particular the alcohols sold under the name Jarcol by the company Jarchem Industries, such as Jarcol 1-12, Jarcol 1-16, Jarcol I-20 and Jarcol I-24.
  • the oil is chosen from:
  • C6-C50 saturated or unsaturated C6-C50, especially C6-C32, in particular C8-C28, monoalcohols, and in particular isostearyl alcohol, cetyl alcohol, oleyl alcohol, isopalmitoyl alcohol, lauryl alcohol, 2-butyloctanol, 2-hexyldecanol, 2-octyldecanol, 2-octyldodecanol, 2-octyltetradecanol, 2-decyltetradecanol, 2-dodecylhexadecanol; and/or
  • glossy oils for which the refractive index at 25°C is indicated between parentheses, may be used: poly- glyceryl-3 diisostearate (1 .472), phytantriol (1 .467), castor oil (1 .475), 2-octyl- 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), 2-butyloctanol, 2-hexyldecanol (1 .45), 2-decyltetradecanol (1 .457), and also mixtures thereof.
  • the oils that can be used in the present invention are chosen from 2-octyldodecanol, diisostearyl malate, 2-butyloctanol, 2-hexyldecanol, 2-decyltetradecanol; hydrogenated or nonhydrogenated castor oil, and also derivatives thereof; hydroxylated modified soybean oil, and mixtures thereof.
  • the joining group which can be used to form compound A according to the invention bears at least one reactive group, in particular isocyanate or imidazole (preferably isocyanate), capable of reacting with the reactive functions, in particular OH and/or NH 2 (exclusively NH 2 for imidazole), of the oil, so as to form a covalent bond, in particular of urethane type, between said oil and said joining group.
  • a reactive group in particular isocyanate or imidazole (preferably isocyanate)
  • the reactive functions in particular OH and/or NH 2 (exclusively NH 2 for imidazole)
  • Said joining group is capable of establishing H bonds with one or more partner joining groups, of identical or different chemical nature, each pairing of a joining group involving at least 3 H (hydrogen) bonds, preferably at least 4 H bonds, pref- erentially 4 H bonds.
  • joining group is intended to mean any functional group comprising groups which donate or accept H bonds, and capable of establishing at least three H bonds, preferably at least 4 H bonds, preferentially 4 H bonds, with an identical or different partner joining group.
  • partner joining group is intended to mean any joining group which can establish H bonds with one or more joining groups of the same or of another polymer according to the invention.
  • the joining groups may be of identical or different chemical nature. If they are identical, they can then establish H bonds between one another and are then referred to as self- complementary joining groups. If they are different, they are chosen such that they are complementary with respect to H interactions.
  • joining group bearing isocyanate groups
  • (G)-(NCO) p bearing isocyanate groups
  • p being a non-zero integer, preferably equal to 1 or 2.
  • the joining group comprises, moreover, at least one monovalent unit of formula (la) and/or at least one divalent unit of formula (lb):
  • R1 and R3 which may be identical or different, represent a divalent carbon- based radical chosen from (i) a linear or branched C1 -C32 alkyl group, (ii) a C 4 -Ci6 cycloalkyl group and (iii) a C 4 -Ci6 aryl group; said groups optionally comprising 1 to 8 heteroatoms chosen from O, N, S, F, Si and P; and/or said groups being optionally substituted with an ester or amide function or with a C1 -C12 alkyl radical; or a mixture of these groups;
  • R2 and R4 independently of one another, represent a hydrogen atom or a linear, branched or cyclic, saturated or unsaturated, optionally aromatic, C1 -C32 carbon- based, in particular hydrocarbon-based (alkyl) radical which can comprise one or more heteroatoms chosen from O, N, S, F, Si and P.
  • the joining group comprises at least one monovalent unit of formula (la).
  • the R1 radical may in particular be:
  • R1 represents -isophorone-, -(CH 2 )6- or 4,4'- methylenebiscyclohexylene.
  • R2 or R4 radicals independently of one another, may be H or else:
  • an arylalkoxy group in particular a (Ci-C 4 ) arylalkoxy group
  • R2 represents H, CH 3 , ethyl, C13H2 7 , C7H 15, phenyl, isopropyl, isobutyl, n-butyl, tert-butyl, n-propyl, or else -CH(C 2 H 5 )(C 4 H 9 ).
  • R4 H.
  • R3 represents a divalent radical -R'3-O-C(O)-NH-R'4- in which R'3 and R'4, which may be identical or different, represent a divalent carbon-based radical chosen from a linear or branched C1-C32 alkyl group or a C 4 -Ci6 cycloalkyl group or a C 4 -Ci6 aryl group; or a mixture thereof.
  • 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-methylheptylene), 1 ,5-(2,2,5-trimethylhexylene), 1 ,7-(3,7- dimethyloctylene), 4,4'-methylenebiscyclohexylene, 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 or isophorone.
  • R'3 may represent a Ci-C 4 alkylene, in particular 1 ,2-ethylene.
  • R'4 may represent the divalent radical derived from isophorone.
  • R3 may have the structure:
  • R1 represents the radical -isophorone-
  • R2 methyl
  • R3 -(CH 2 ) 2 OCO-NH-isophorone-, which results in the divalent unit of formula:
  • the joining groups bearing a single isocyanate function may be of formula:
  • R1 and R2 are as defined above; and in particular:
  • - R1 represents -isophorone-, -(CH 2 ) 6 -, -CH 2 CH(CH3)-CH2-C(CH3)2-CH2-CH2, 4,4'- methylenebiscyclohexylene or 2-methyl-1 ,3-phenylene; and/or
  • - R2 represents H, CH 3 , ethyl, C13H27, C7H15, phenyl, isopropyl, isobutyl, n-butyl, tert-butyl, n-propyl, or else -CH(C 2 H 5 )(C 4 H 9 ).
  • the joining groups may be chosen from the following groups:
  • the joining groups bearing two isocyanate functions may be of formula:
  • R1 , R2 and R3 are as defined above, and in particular:
  • R1 represents -isophorone-, -(CH 2 ) 2 -, -(CH 2 ) 6 -, -CH 2 CH(CH3)-CH2-C(CH 3 )2-CH2- CH 2 , 4,4'-methylenebiscyclohexylene or 2-methyl-1 ,3-phenylene; and/or
  • - R2 represents H, CH 3 , ethyl, C13H27, C7H15, phenyl, isopropyl, isobutyl, n-butyl, tert-butyl, n-propyl, or else -CH(C2H 5 )(C 4 H 9 ); and/or
  • R3 represents a divalent radical -R'3-O-C(O)-NH-R'4- in which R'3 and R'4, which may be identical or different, represent a divalent carbon-based radical chosen from a linear or branched C1-C30 alkyl group or a C 4 -Ci2 cycloalkyl group or a C 4 -Ci2 aryl group; or mixtures thereof; and in particular R'3 represents a Ci-C 4 al- kylene, in particular 1 ,2-ethylene, and R'4 represents the divalent radical derived from isophorone.
  • a joining group which is most particularly preferred is that of formula:
  • the joining groups may be attached to the oil via functionalization of the joining group with an isocyanate or imidazole.
  • the supramolecular compound A according to the invention (which may, for convenience, also be referred to as supramolecu- lar oil in the present text) 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 .
  • the oil comprises only hydroxyl functions and the joining group comprises 1 or 2 isocyanate functions, which results in the following reactions:
  • the degree of grafting of the free OHs of the oil is between 1 % and 100%, in particular between 20% and 99%, and better still between 50% and 95%; preferably, this degree is 100% (all the free OHs are functionalized with a joining group), in particular when the oil initially comprises only one OH function.
  • the supramolecular compound A according to the invention can be prepared by means of the processes normally used by those skilled in the art to form a ure- thane bond, between the free OH functions of the oil and the isocyanate functions borne by the joining group.
  • a general preparation process consists in:
  • the reaction can be carried out in the presence of a solvent or of a mixture of solvents, in particular methyltetrahydrofuran, tetrahydrofuran, toluene or butyl acetate, or even propylene carbonate, in particular as cosolvent; the reaction can also be carried out without solvent, it being possible for the oil to then act as a solvent. It is also possible to add a catalyst conventional for the formation of a urethane bond. By way of example, mention may be made of dibutyltin dilaurate.
  • the reaction can 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
  • the supramolecular compounds A according to the invention can in particular correspond to the following structures:
  • compound A 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 still between 750 and 3000 mPa.s.
  • the number-average molecular weight (Mn) of the compound according to the in- vention is preferably between 180 and 8000, preferably 200 to 6000, or even from 300 to 4000, and even better still from 400 to 3000, preferentially from 500 to 1500.
  • the supramolecular compound A according to the invention (also referred to as "supramolecular compound derived from an oil” or “H-bond-generating oil” or else supramolecular oil) is advantageously soluble in the cosmetic oily media normally used, and in particular in plant oils, C6-C32 alkanes, C8-C32 fatty esters, C2-C7 short esters, C8-C32 fatty alcohols, and more particularly in media comprising at least isododecane, sesam, isononyl isononanoate, octyldodecanol, C12-C15 alkyl ben- zoate, butyl acetate, ethyl acetate, alone or as a mixture.
  • soluble is intended to mean that the supramolecular compound A forms a clear solution in at least one solvent chosen from isododecane, sesam, isononyl isononanoate, octyldodecanol, C12-C15 alkyl benzoate, butyl acetate and ethyl acetate, in a proportion of at least 50% by weight, at 25°C.
  • Said supramolecular compound A (also referred to as supramolecular oil), alone or as a mixture, may be present in the compositions according to the invention in an amount which may be between 0.5% and 99% by weight, preferably between 0.5% and 50% by weight, in particular between 1 % and 40% by weight, or even between 1 .5% and 20% by weight, and better still between 2% and 15% by weight, relative to the weight of the final cosmetic composition.
  • a composition according to the invention may comprise from 0.1 % to 60% by weight of supramolecular compound A (also referred to as supramolecular oil), relative to the total weight of the composition.
  • supramolecular compound A also referred to as supramolecular oil
  • it may comprise from 0.2% to 50% by weight of supramoleclar compound A, relative to the total weight of the composition.
  • it may comprise from 0.5% to 40% by weight of supramolecular compound A, relative to the total weight of the composition.
  • compositions according to the invention thus comprise a polyalkene- based (i.e. polyolefin-based) supramolecular polymer, also referred to as "com- pound B”.
  • polyalkene-based supramolecular polymer is intended to mean a polymer resulting from the reaction, in particular from the condensation, of at least one polyalkene polymer functional- ized with at least one reactive group, with at least one joining group functionalized with at least one reactive group capable of reacting with the reactive group(s) of the functionalized polyalkene polymer, said joining group being capable of forming at least 3 H (hydrogen) bonds, preferably at least 4 H bonds, preferentially 4 H bonds.
  • said functionalized polyalkene is hydrogenated.
  • polyalkene or "polyolefin” is intended to mean a polymer resulting from the polymerization of at least one monomer of alkene type, comprising an ethylenic unsaturation, it being possible for said monomer to be pendant or in the main chain of said polymer.
  • polyalkene or “polyolefin” thus covers polymers which may or may not comprise a double bond.
  • the su- pramolecular polymers used according to the invention are prepared from a polymer resulting from the polymerization of an alkene comprising at least two ethylenic unsaturations.
  • the supramolecular polymer according to the invention is capable of forming a su- pramolecular polymeric chain or network by (self)assembly of said polymer according to the invention with at least one other polymer according to the invention, which may be identical or different, each assembly involving at least one pair of identical or different paired joining groups, borne by each of the polymers according to the invention.
  • joining group is intended to mean any group comprising groups which donate or accept H bonds, and capable of establishing at least three H bonds, preferably at least 4 H bonds, preferably 4 H bonds, with a partner joining group, which may be identical or different.
  • These joining groups may be lateral to the polymer backbone (in a side branch), and/or borne by the ends of the polymer backbone, and/or in the chain forming the polymer backbone. They may be distributed in a random or controlled manner.
  • the polyalkene polymers are functionalized with at least one reactive group, preferably with at least two reactive groups.
  • the functionalization is preferably carried out at the chain ends.
  • the term telechelic polymers is then used.
  • the functionalization groups, or reactive groups may be attached to the polyal- kene polymer via linkers, preferably linear or branched Ci-C 4 alkylene groups, or directly via a single bond.
  • the functionalized polyalkene polymers have a number-average molecular weight (Mn) of between 1000 and 8000.
  • they have a number-average molecular weight of between 1000 and 5000, or even between 1500 and 4500.
  • the functionalized polyalkene polymer capable of forming all or part of the polymer backbone of the supramolecular polymer according to the invention is of formula HX-P-X'H in which:
  • - XH and X'H are reactive functions, with X and X', which may be identical or different, chosen from O, S, NH, NCO or NR a , R a representing a C1-C6 alkyl group; preferably, X and/or X' denote O; preferentially, X and X' denote O;
  • - P represents a homopolymer or copolymer which can be obtained by polymerisation of one or more linear, cyclic and/or branched, monounsaturated or polyun- saturated, C2-C10, preferably C2-C 4 , alkenes; P preferably represents a homopolymer or copolymer which can be obtained by polymerisation of one or more monounsaturated, linear or branched C2-C 4 alkenes.
  • the functionalized polyalkene polymer capable of forming all or part of the polymer backbone of the supramolecular polymer according to the invention (it preferably forms the entire backbone of the polymer), is of formula HO-P-OH in which:
  • - P represents a homopolymer or a copolymer which can be obtained by polymerisation of one or more linear, cyclic and/or branched, polyunsaturated (preferably diunsaturated), C2-C10, preferably C2-C 4 , alkenes.
  • P preferably represents a homopolymer or a copolymer which can be obtained by polymerisation of one or more diunsaturated, linear or branched, C2-C 4 alkenes. More preferably, P represents a polymer chosen from a polyethylene, a polybuty- lene, a polybutadiene (such as a 1 ,4-polybutadiene or a 1 ,2-polybutadiene), a polyisoprene, a poly(1 ,3-pentadiene), a polyisobutylene, and copolymers thereof, and in particular a poly(ethylene/butylene).
  • P represents a poly(ethylene/butylene) copolymer.
  • the preferred poly(ethylene/butylene)s are copolymers of 1 -butene and of ethylene. They can be represented schematically by the sequence of following units: [-CH2-CH2-] and [-CH 2 CH(CH 2 -CH 3 )-].
  • P is a polybutadiene homopolymer, preferably chosen from a 1 ,4-polybutadiene or a 1 ,2-polybutadiene.
  • they are 1 ,2-polybutadienes.
  • P is a 1 ,2- polybutadiene homopolymer.
  • P is a polyisoprene.
  • the polyisoprenes can be represented schematically by the sequences of following units:
  • the functionalized polyalkene polymers may be hydrogenated, in particular completely hydrogenated, in order to avoid risks of crosslinking.
  • the functionalized polyalkene polymers used in the compositions according to the invention are hydrogenated.
  • the supramolecular polymers may also comprise in their structure other units derived from other monomers.
  • comonomers mention may in particular be made of styrene or monomers having an epoxy group. In one preferred embodiment, they do not comprise them and therefore consist solely of polyalkene polymers (100%) to form the polymer backbone.
  • polyalkenes P as defined above, with P preferably representing a homopolymer or a copolymer which can be obtained by polymerisation of one or more monoun- saturated, linear or branched, C2-C 4 alkenes, P more preferably representing a polymer chosen from a polyethylene, a polybutylene, a polybutadiene, a polyiso- prene, a poly(1 ,3-pentadiene), a polyisobutylene, and copolymers thereof, and preferentially a poly(ethylene/butylene).
  • P preferably representing a homopolymer or a copolymer which can be obtained by polymerisation of one or more monoun- saturated, linear or branched, C2-C 4 alkenes
  • the polyalkene polymers are functionalized with at least one reactive group, preferably with at least two reactive groups.
  • the functionalization is preferably carried out at the end of chains.
  • the term telechelic polymers is then used.
  • the reactive group may be attached to the polyalkene polymer via linkers, preferably linear or branched Ci-C 4 alkylene groups, or directly via a single bond.
  • linkers preferably linear or branched Ci-C 4 alkylene groups, or directly via a single bond.
  • reactive group mention may be made of OH, NH 2 , NHR, SH or NCO functions.
  • the polyalkene polymers can be functionalized with OH groups, preferably at the ends. Preferably, they exhibit a functionality with respect to hydroxyl ends of 1 .8 to 3, and preferably in the region of 2.
  • the polyalkene polymers are hydrogenated and functionalized with at least two reactive groups X and X' as defined above, with X and/or X' denoting O.
  • X and X' denote O.
  • polydienes preferably hydrogenated polydienes, comprising hydroxyl functions, preferably comprising hydroxyl ends, and polyolefins comprising hydroxyl ends, and in particular chosen from homopolymers and copolymers of poly- butadiene, polyisoprene and of poly(1 ,3-pentadiene).
  • the polydienes comprising hydroxyl ends and in particular defined, for example, in FR2782723. They may be chosen from homopolymers and copolymers of polybu- tadiene, polyisoprene and of poly(1 ,3-pentadiene). Mention will in particular be made of the hydroxylated polybutadienes sold by the company Sartomer, such as Krasol® Resins and Poly bd® Resins.
  • they are dihydroxylated hydrogenated 1 ,2-polybutadiene homopolymers, such as the Nisso-PB I, GI3000, GI2000 and GI1000 range sold by the company Nisso, which can be represented schematically by the following formula:
  • n is between 14 and 105, preferably between 20 and 85.
  • the polystyrene standards are prepared using the Varian kits (ref: PS-H (PL2010- 0200))
  • the weights of the standards are the following:
  • the solution is prepared approximately 24 h before injection.
  • the solution is filtered through a Millex FH filter (0.45 ⁇ ).
  • PL-Rapid-F (6M-0L1 -01 1 -6) from Polymer Labs Length: 150 mm - internal diameter : 7.5 mm
  • polyolefins comprising hydroxyl ends
  • the supramolecular polymers according to the invention also have, in their structure, at least one residue of a joining group capable of forming at least 3 H bonds, preferably at least 4 H bonds, said joining group being initially functionalized with at least one reactive group.
  • joining group is intended to mean, in the present description, the group without its reactive function.
  • the reactive groups are attached to the joining group via linkers L or directly via a single bond.
  • the linker (L) is a saturated or unsaturated, C1-C20 divalent carbon- based group, in particular chosen from a linear or branched C1-C20 alkylene, a C 5 - C20 (alkyl)cycloalkylene alkylene (preferably cyclohexylene methylene), a C11-C20 alkylene-biscycloalkylene (preferably alkylene-biscyclohexylene), a C6-C20 (al- kyl)arylene, and an alkylene-bisarylene (preferably an alkylene-bisphenylene), it being possible for the linker L to be substituted with at least one alkyl group and/or to optionally comprise 1 to 4 heteroatoms N and/or O, in particular in the form of an NO2 substituent.
  • the linker is chosen from a phenylene; 1 ,4-nitrophenyl; 1 ,2-ethylene;
  • the linker is chosen from the groups:
  • alkyl cycloalkylene alkylene, such as isophorone
  • -C1-C20 alkylene such as -(CH 2 ) 2 -; -(CH 2 ) 6 -; -CH 2 CH(CH3)-CH2-C(CH3)2-CH 2 -CH2, and
  • L is chosen from: -isophorone-; -(CH 2 ) 2 -; -(CH 2 ) 6 -; -CH 2 CH(CH 3 )-CH 2 - C(CH 3 )2-CH2-CH 2 ; 4,4'-methylenebiscyclohexylene and 2-methyl-1 ,3-phenylene.
  • the linker is an alkylcycloal- kylene alkylene.
  • the linker is an isophorone group.
  • isophorone is intended to mean the following group:
  • Said reactive groups functionalizing the joining group should be capable of react- ing with the reactive group(s), in particular -OH group(s), borne by the functional- ized polyalkene.
  • the functionalized joining groups capable of forming at least 3 H bonds can comprise at least 3 identical or different functional groups preferably at least 4, chosen from: ⁇ ⁇ ⁇ ⁇ ⁇ ⁇
  • the joining groups capable of forming at least 3 H bonds form a base structural element comprising at least 3 functional groups, preferably at least 4 functional groups, and more preferentially 4 functional groups capable of establishing H bonds.
  • Said base structural elements capable of establishing H bonds can be represented schematically in the following way:
  • X 4 or Y 4 is a functional group which accepts H bonds (which may be identical or different) and Y, is a functional group which donates H bonds (which may be iden- tical or different).
  • each structural element must be able to establish H bonds with one or more partner structural elements which are identical (i.e. self-complementary) or different, such that each pairing of two partner structural elements takes place by formation of at least three H bonds, preferably at least four H bonds, and more pref- erentially 4 H bonds.
  • the joining groups capable of forming at least 3, or even at least 4 H bonds are chosen from the following family, it being understood that all the tautomeric forms are included:
  • -R'i represents a single bond, a hydrogen atom, a halogen atom or a linear, branched and/or cyclic, saturated or unsaturated, optionally aromatic, C1-C30 monovalent carbon-based (in particular alkyl) group which can contain one or more heteroatoms such as O, S, or N;
  • the R'i radical may in particular be a C 4 -Ci2 cycloalkyl group; a linear or branched C1-C30 alkyl group or a C 4 -Ci2 aryl group; optionally substituted with an amino, thio and/or hydroxyl function.
  • R'i is a C 4 H 9 ; phenyl ; 1 ,4-nitrophenyl; 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-methylheptylene); 1 ,5-(2,2,5-trimethylhexylene); 1 ,7-(3,7- dimethyloctylene); -isophorone-; 4,4'-methylenebiscyclohexylene; tolylene; 2- methyl-1 ,3-phenylene; 4-methyl-1 ,3-phenylene or 4,4-bisphenylenemethylene group; or a single bond.
  • R'i represents -isophorone-; -(CH 2 ) 2 -; -(CH 2 ) 6 -; -CH 2 CH(CH 3 )-CH 2 -
  • -R' 2 represents a single bond, a divalent group of C1-C6 alkylene type, or a mono- valent group chosen from a hydrogen atom or a linear, branched and/or cyclic, saturated or unsaturated, optionally aromatic, C1-C30 monovalent hydrocarbon-based group which can contain one or more heteroatoms such as O, S or N;
  • R' 2 can be a single bond or H, a C1-C30 alkyl group; a C 4 -Ci 2 cycloalkyl group; a C 4 -Ci 2 aryl group; a (C 4 -Ci 2 )aryl(CrCi 2 )alkyl group; these groups being optionally substituted with an amino, thio and/or hydroxyl function.
  • R' 2 represents H, CH 3 , CH 2 OH, (CH 2 ) 2 -OH, Ci 3 H 27 , C 7 Hi 5 or phenyl; or a single bond;
  • R'3 represents a hydrogen atom or a linear, branched and/or cyclic, saturated or unsaturated, optionally aromatic, C1-C30 monovalent hydrocarbon-based group which can contain one or more heteroatoms such as O, S or N;
  • R'3 can be a C 4 -Ci 2 cycloalkyl group; a linear or branched C1-C30 alkyl group or a C 4 -Ci 2 aryl group; optionally substituted with an amino, thio and/or hydroxyl function; preferentially, R'3 represents H, CH 3 , CH 2 OH or (CH 2 ) 2 -OH, and even better still methyl;
  • R'i radicals are single bonds constituting the point of attachment of the joining group to the linker capable of forming at least 3 H bonds (preferably 4) on the rest of the graft.
  • said point of attachment is borne only by R'i which is a single bond;
  • the R' 2 radical represents a divalent group chosen from a single bond or a C1-C6 alkylene, or a monovalent group chosen from a single bond, a hydrogen atom, or a linear or branched, saturated, C1-C10 monovalent hydrocarbon-based group which can contain one or more heteroatoms such as O, S, or N, these groups being optionally substituted with a hydroxyl, amino and/or thio function.
  • the R'2 radical may be a single bond or a monovalent group chosen from H, CH2OH, (CH 2 ) 2 -OH and CH 3 .
  • R' 2 is H
  • R'3 radical represents a divalent or monovalent group; in particular, R' 3 is chosen from a hydrogen atom or a linear or branched, saturated, C1-C10 monova- lent hydrocarbon-based group which can contain one or more heteroatoms such as O, S or N, said hydrocarbon-based group being optionally substituted with a hydroxyl, amino and/or thio function.
  • the R'3 radical may be a monovalent group chosen from H, CH 2 OH, (CH 2 ) 2 -OH and CH 3 .
  • R' 3 is a methyl group.
  • the joining groups are chosen from 2- ureidopyrimidone and 6-methyl-2-ureidopyrimidone.
  • the preferred joining group is 6-methyl-2-ureidopyrimidone.
  • the joining groups and in particular the ureidopyrimidone joining groups, can be added directly or else formed in situ during the process for preparing the supramo- lecular polymer.
  • the first and second preparation modes described hereinafter illustrate, respectively, these two alternatives.
  • the functionalized joining groups capable of reacting with the func- tionalized polyalkene polymer so as to give the supramolecular polymer according to the invention are preferably of formula (III) and preferentially of formula (IV):
  • L is a single bond or a linker as defined above;
  • L is a linear, cyclic and/or branched, saturated or unsaturated, or even aromatic, Ci-C 2 o divalent carbon-based (alkylene) group, optionally comprising 1 to 4 N and/or O heteroatoms, in particular in the form of an NO 2 substituent, and in particular a phenylene; 1 ,4-nitrophenyl; 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-methylheptylene); 1 ,5-(2,2,5-trimethylhexylene); 1 ,7-(3,7- dimethyloctylene); -isophorone-; 4,4'-methylenebiscyclohexylene; tolylene; 2- methyl-1 ,3-phenylene; 4-methyl-1
  • L is -isophorone-; -(CH 2 ) 2 -; -(CH 2 ) 6 -; -CH 2 CH(CH3)-CH2-C(CH 3 )2-CH2- CH 2 ; 4,4'-methylenebiscyclohexylene or 2-methyl-1 ,3-phenylene; and better still isophorone;
  • R'2 represents a single bond, a divalent group of C1-C6 alkylene type, or a monovalent group chosen from a hydrogen atom or a linear, branched and/or cyclic, saturated or unsaturated, optionally aromatic, C1-C30 monovalent hydrocarbon-based group which can contain one or more heteroatoms such as O, S or N;
  • R'2 can be a single bond or H, a Ci-C3o alkyl group; a C 4 -Ci2 cycloalkyl group; a C 4 -Ci2 aryl group; a (C 4 -Ci2)aryl(CrCi2)alkyl group; these groups being optionally substituted with an amino, ester and/or hydroxyl function.
  • R' 2 represents H, CH 3 , CH 2 OH, (CH 2 ) 2 -OH, Ci 3 H 27 , C 7 Hi 5 or phenyl; or a single bond;
  • R'3 represents a hydrogen atom or a linear, branched and/or cyclic, saturated or unsaturated, optionally aromatic, C1-C30 monovalent hydrocarbon-based group which can contain one or more heteroatoms such as O, S or N;
  • R'3 may be a C 4 -Ci2 cycloalkyl group; a linear or branched C1-C30 alkyl group or a C 4 -Ci2 aryl group; optionally substituted with an amino, ester and/or hydroxyl function; preferentially, R'3 represents H, CH 3 , CH 2 OH or (CH 2 )2-OH; and even better still methyl.
  • the R'2 radical represents a divalent group chosen from a single bond or a C1-C6 alkylene, or a monovalent group chosen from a single bond, a hydrogen atom, or a linear or branched, saturated, C1-C10 monovalent hydrocarbon-based group which can contain one or more heteroatoms such as O, S or N, these groups being optionally substituted with a hydroxyl, amino and/or thio function.
  • the R'2 radical may be a single bond or a monovalent group chosen from H, CH2OH, (CH 2 ) 2 -OH and CH 3 .
  • R' 2 is H.
  • the R'3 radical represents a divalent or monovalent group
  • R'3 is chosen from a hydrogen atom or a linear or branched, saturated, C1-C10 monovalent hydrocarbon-based group which can contain one or more heteroatoms such as O, S or N, said hydrocarbon-based group being optionally substituted with a hydroxyl, amino and/or thio function.
  • the R'3 radical may be a monovalent group chosen from H, CH 2 OH, (CH 2 ) 2 -OH and CH 3 .
  • R' 3 is a methyl group.
  • L is chosen from the groups: - C5-C20 (alkyl)cycloalkylene alkylene, such as isophorone,
  • - C1-C20 alkylene such as -(CH 2 ) 2 -; -(CH 2 ) 6 -; -CH 2 CH(CH3)-CH2-C(CH3)2-CH 2 -CH2, and
  • L is chosen from: -isophorone-; -(CH 2 )6- and 4,4'- methylenebiscyclohexylene.
  • the joining group is of formu-
  • the supramolecular polymer of the invention corresponds to the formula:
  • L' and L" represent a saturated or unsaturated, linear, cyclic and/or branched, C1-C20 divalent carbon-based (alkylene) group.
  • L' and L" are chosen from a linear or branched C1-C20 alkylene, a C5-C20 (alkyl)cycloalkylene, an alkylene-biscycloalkylene and a C6-C20 (alkyl)arylene.
  • L' and L" represent an -isophorone-; -(CH 2 ) 2 -; -(CH 2 ) 6 -; -CH 2 CH(CH3)-CH2-C(CH3)2-CH2-CH 2 ; 4,4'-methylenebiscyclohexylene or 2-methyl-1 ,3-phenylene group.
  • L' and L" are identical.
  • L' and L" are an isophorone group.
  • P represents a polyethylene, a polybutylene, a polybutadiene, a poly- isoprene, a poly(1 ,3-pentadiene), a polyisobutylene, or one of their copolymers, in particular a poly(ethylene/butylene), and is preferably hydrogenated.
  • P is a hydrogenated polybutadiene, preferably a hydrogenated 1 ,2- polybutadiene.
  • the supramolecular polymer of the in- ention corresponds to the formula:
  • n is such that the number-average molecular weight (Mn) of said polymer is between 1000 and 8000, in particular between 1000 and 5000, or even be- tween 1500 and 4500, and even better still between 2000 and 4000.
  • Mn number-average molecular weight
  • the polymer according to the invention can be prepared by means of the processes usually employed by those skilled in the art, in particular in order to form a urethane bond between the free OH functions of a polyalkene and the iso- cyanate functions borne by the joining group.
  • a first general preparation process consists in:
  • said polymer comprising at least one reactive function, in particular 2 reactive functions, in particular OH, to a temperature which can be between 60°C and 140°C, it being possible for the hydroxyl number of the polymer to act as reference in order to measure the state of progression of the reaction;
  • the joining group in particular the ureidopyrimidone group, bearing the reactive functions, in particular isocyanate reactive functions, such as those described in patent WO 2005/042641 ; in particular such as the joining groups of cas number 32093-85-9 and 709028-42-2;
  • the reaction can also be monitored by quantitative determinations of the hydroxyl functions; it is also possible to add ethanol in order to make sure that the residual isocyanate functions have completely disappeared.
  • the reaction can be carried out in the presence of a solvent, in particular methylte- trahydrofuran, tetrahydrofuran, toluene, propylene carbonate or butyl acetate. It is also possible to add a catalyst that is conventional for the formation of the urethane bond. By way of example, mention may be made of dibutyltin dilaurate. At the end, the polymer can be washed and dried, or even purified, according to the general knowledge of those skilled in the art.
  • the reaction can comprise the following steps:
  • the diisocyanate can optionally be in excess with respect to the polymer.
  • This first step can be carried out in the presence of solvent, at a temperature of between 20°C and 100°C. This first step can be followed by a period of stirring, under a controlled atmosphere, for 1 to 24 hours. The mixture can be optionally heated. The state of progression of this first step can be monitored by quantitative deter- mination of the hydroxyl functions;
  • this second step can optionally be carried out in the presence of a cosolvent, such as toluene, butyl acetate or propylene carbonate.
  • a cosolvent such as toluene, butyl acetate or propylene carbonate.
  • the reaction mixture can be heated at between 80°C and 140°C for a period of time varying between 1 and 24 hours.
  • a catalyst in particular dibutyltin dilaurate, can promote the production of the desired final product.
  • the reaction can be monitored by infrared spectroscopy, by monitoring the disappearance of the peak characteristic of the isocyanate between 2200 and 2300 cm "1
  • ethanol can be added to the reaction medium in order to neutralize the possible residual isocyanate functions.
  • the reaction mixture can be optionally filtered.
  • the polymer can also be directly stripped in a cosmetic solvent.
  • said supramolecular polymer is solubi- lized in a hydrocarbon-based, preferably volatile, oil, in particular isododecane.
  • composition of the invention will comprise at least one hydrocarbon- based, preferably volatile, oil, in particular at least isododecane, especially provided by the solution of supramolecular polymer.
  • the supramolecular polymer(s) may be present in a composition according to the invention in a content ranging from 0.1 % to 99% by weight of dry matter, relative to the total weight of the composition.
  • the supramolecular polymer(s) may be present in a composition according to the invention in a content ranging from 1 % to 80% by weight of dry matter, relative to the total weight of the composition.
  • the supramolecular polymer(s) may be present in a composition according to the invention in a content ranging from 2% to 70% by weight of dry matter, relative to the total weight of the composition. According to an even more preferred variant, the supramolecular polymer(s) may be present in a composition according to the invention in a content ranging from 3% to 60% by weight of dry matter, relative to the total weight of the composition.
  • the supramolecular polymer(s) may be present in a composition according to the invention in a content ranging from 4% to 50% by weight, relative to the total weight of the composition.
  • the supramolecular polymer(s) may be present in a composition according to the invention in a content ranging from 5% to 40% by weight, relative to the total weight of the composition.
  • a makeup composition is provided in the form of a composition for the skin, in particular of the face, or the lips, and the supramolecular polymer(s) may be present therein in a content ranging from 2.5% to 60% by weight of dry matter, relative to the total weight of the composition.
  • a makeup composition is provided in the form of a composition for the skin, in particular of the face, or the lips, and the supramolecular polymer(s) may be present therein in a content ranging from 2.5% to 40% by weight of dry matter, relative to the total weight of the composition.
  • a makeup composition is provided in the form of a composition for the skin, in particular of the face, or the lips, and the supramolecular polymer(s) may be present therein in a content ranging from 3% to 30% by weight of dry matter, relative to the total weight of the composition.
  • a composition according to the invention in particular in the case of a makeup composition for the skin and/or the lips, comprises at least one supramolecular polymer (compound B) and at least one supramolecular compound A derived from an oil (also referred to as supramolecular oil) in a supramolecular polymer/supramolecular oil weight ratio of between 0.01 and 50.
  • they are present in a weight ratio of between 0.1 and 20.
  • a composition according to the invention in particular in the case of a makeup composition for the skin and/or the lips, comprises a content of su- pramolecular polymer (compound B) of between 5% and 99% by weight, relative to the weight of the composition excluding volatile compound(s) (in particular relative to the weight of the composition excluding volatile oil(s), such as isododecane for example).
  • This content reflects the resulting content of supramolecular polymer(s) in a deposit made with the compositions according to the invention, in particular on keratin materials such as the skin and/or the lips, for example, after evaporation of the volatile compounds.
  • the composition according to the invention in particular in the case of a makeup composition, comprises a content of supramolecular polymer (compound B) of between 10% and 90% by weight, relative to the weight of the composition excluding volatile compound(s), preferably between 15% and 80%.
  • the cosmetic compositions according to the invention comprise, moreover, a cosmetically acceptable medium, i.e. a medium compatible with keratin materials such as the skin of the face or of the body, the eyelashes, the eyebrows, the lips and the nails.
  • a cosmetically acceptable medium i.e. a medium compatible with keratin materials such as the skin of the face or of the body, the eyelashes, the eyebrows, the lips and the nails.
  • Said medium may comprise a liquid fatty phase, which may comprise at least one compound chosen from volatile or non-volatile carbon-based, hydrocarbon-based and/or silicone and/or fluoro oils and/or solvents of mineral, animal, plant or synthetic origin, alone or as a mixture, provided that they form a uniform, stable mix- ture and are compatible with the intended use.
  • a liquid fatty phase which may comprise at least one compound chosen from volatile or non-volatile carbon-based, hydrocarbon-based and/or silicone and/or fluoro oils and/or solvents of mineral, animal, plant or synthetic origin, alone or as a mixture, provided that they form a uniform, stable mix- ture and are compatible with the intended use.
  • compositions according to the invention comprise at least one volatile or non-volatile oil.
  • oil is intended to mean a water-immiscible, non-aqueous compound which is liquid at ambient temperature (25°C) and atmospheric pressure (760 mmHg).
  • volatile is intended to mean any compound that is capable of evaporating on contact with keratin materials, or the lips, in less than one hour, at ambient temperature (25°C) and atmospheric pressure (1 atm).
  • this volatile compound has a non-zero vapour pressure, at am- bient temperature and atmospheric pressure, especially ranging from 0.13 Pa to 40 000 Pa, in particular ranging from 1 .3 Pa to 13 000 Pa, and more particularly ranging from 1 .3 Pa to 1300 Pa.
  • non-volatile is intended to mean a compound that remains on keratin materials or the lips at ambient temperature and atmospheric pressure for at least one hour, and which in particular has a vapour pressure of less than 10 "3 mmHg (0.13 Pa).
  • the physiologically acceptable medium of the composition according to the invention may comprise, in a liquid fatty phase, at least one oil and/or one solvent which can be chosen, alone or as a mixture, from:
  • esters of monocarboxylic acids with monoalcohols and polyalcohols advanta- geously, said ester is a C12-C15 alkyl benzoate or corresponds to the following formula: R'i-COO-R' 2 in which:
  • R'i represents a linear or branched alkyl radical of 1 to 40 carbon atoms and preferably of 7 to 19 carbon atoms, optionally comprising one or more ethylenic double bonds, optionally substituted, and the hydrocarbon-based chain of which may be interrupted with one or more heteroatoms chosen from N and O and/or one or more carbonyl functions, and
  • R'2 represents a linear or branched alkyl radical of 1 to 40 carbon atoms, preferably 3 to 30 carbon atoms and better still 3 to 20 carbon atoms, optionally comprising one or more optionally substituted ethylenic double bonds, and the hydrocar- bon-based chain of which may be interrupted with one or more heteroatoms chosen from N and O and/or one or more carbonyl functions.
  • R'i and/or R' 2 may bear one or more substituents chosen, for example, from groups comprising one or more heteroatoms chosen from O and/or N, such as amino, amine, alkoxy and hydroxyl .
  • groups R'i are those derived from fatty acids, preferably higher fatty acids, chosen from the group formed by acetic acid, propionic acid, butyric acid, caproic acid, caprylic acid, pelargonic acid, capric acid, undecanoic acid, lauric acid, myristic acid, palmitic acid, stearic acid, isostearic acid, arachidic acid, behenic acid, oleic acid, linolenic acid, linoleic acid, oleostearic acid, arachidonic acid and erucic acid, and mixtures thereof.
  • R'i is a branched, unsubstituted alkyl group of 4 to 14 carbon atoms and preferably of 8 to 10 carbon atoms
  • R'2 is a branched, unsubstituted alkyl group of 5 to 15 carbon atoms and preferably of 9 to 1 1 carbon atoms.
  • Hydrocarbon-based plant oils with a high triglyceride content formed from fatty acid esters of glycerol in which the fatty acids may have varied chain lengths from C 4 to C2 4 , these chains possibly being linear or branched, and saturated or unsaturated; these oils are especially wheatgerm oil, corn oil, sunflower oil, shea oil, castor oil, sweet almond oil, macadamia oil, apricot oil, soyabean oil, rapeseed oil, cottonseed oil, alfalfa oil, poppy seed oil, pumpkin oil, sesame seed oil, marrow oil, avocado oil, hazelnut oil, grapeseed oil, blackcurrant seed oil, evening primrose oil, millet oil, barley oil, quinoa oil, olive oil, rye oil, safflower oil, candlenut oil, passionflower oil, musk rose oil, jojoba oil, palm oil or beauty-leaf oil; or alternatively ca- prylic/capric acid triglycer
  • C6-C32 and especially C12-C26 monoalcohols for instance oleyl alcohol, linoleyl alcohol, linolenyl alcohol, isostearyl alcohol, 2- hexyldecanol, 2-butyloctanol, 2-undecylpentadecanol and octyldodecanol;
  • volatile or non-volatile hydrocarbon-based oils of synthetic or mineral origin, which may be chosen from hydrocarbon-based oils containing from 5 to 100 carbon atoms, and especially petroleum jelly, polydecenes, hydro- genated polyisobutenes such as sesam, squalane and perhydrosqualene, and mixtures thereof.
  • Volatile silicone oils that may be mentioned include linear or cyclic volatile silicone oils, especially those with a viscosity of less than 8 centistokes, and especially containing from 2 to 10 silicon atoms, these silicones optionally comprising alkyl or alkoxy groups containing from 1 to 22 carbon atoms; and in particular octamethyl- cyclotetrasiloxane, decamethylcyclopentasiloxane, dodecamethylcyclohexa- siloxane, heptamethylhexyltrisiloxane, heptamethyloctyltrisiloxane, hexamethyldisi- loxane, octamethyltrisiloxane, decamethyltetrasiloxane, dodecamethylpenta- siloxane and methylhexyldimethylsiloxane, and mixtures thereof.
  • linear or cyclic volatile silicone oils especially those with a viscosity of less than 8 centist
  • the non-volatile silicone oils that may be used according to the invention may be polydimethylsiloxanes (PDMS), polydimethylsiloxanes comprising alkyl or alkoxy groups, which are pendant and/or at the end of a silicone chain, each group containing from 2 to 24 carbon atoms, phenyl silicones, for instance phenyl trimethi- cones, phenyl dimethicones, phenyltrimethylsiloxydiphenylsiloxanes, diphenyl di- methicones, diphenylmethyldiphenyltrisiloxanes and 2-phenylethyl trimethylsilox- ysilicates.
  • PDMS polydimethylsiloxanes
  • polydimethylsiloxanes comprising alkyl or alkoxy groups, which are pendant and/or at the end of a silicone chain, each group containing from 2 to 24 carbon atoms
  • phenyl silicones for instance phenyl trime
  • the physiologically acceptable medium of the composition according to the invention comprises, in a liquid fatty phase, at least one oil and/or one solvent chosen, alone or as a mixture, from isododecane, sesam, isononyl isonona- noate, octyldodecanol, phenyl trimethicone, C12-C15 alkyl benzoates, butyl and ethyl acetates, and/or D5 (decamethylcyclopentasiloxane).
  • the liquid fatty phase may also comprise additional oils and/or solvents, which may be chosen, alone or as a mixture, from:
  • fluoro oils such as perfluoropolyethers, perfluoroalkanes, for instance perfluoro- decalin, perfluorodamantanes, perfluoroalkyl phosphate monoesters, diesters and triesters and fluoro ester oils;
  • propylene glycol ethers that are liquid at ambient temperature, such as propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate or dipropylene glycol mono-n-butyl ether;
  • - C8-C32 fatty acids for instance oleic acid, linoleic acid or linolenic acid, and mixtures thereof;
  • - difunctional oils comprising two functions chosen from ester and/or amide and containing from 6 to 30 carbon atoms, especially 8 to 28 carbon atoms and better still from 10 to 24 carbon atoms, and 4 heteroatoms chosen from O and N; prefer- ably, the amide and ester functions being in the chain;
  • ketones that are liquid at ambient temperature (25°C) such as methyl ethyl ketone, methyl isobutyl ketone, diisobutyl ketone, isophorone, cyclohexanone and acetone;
  • aldehydes that are liquid at ambient temperature, such as benzaldehyde and acetaldehyde.
  • the liquid fatty phase may represent 1 % to 90% by weight of the composition, especially from 5% to 75% by weight, in particular from 10% to 60% by weight or even from 25% to 55% by weight relative to the total weight of the composition.
  • the composition according to the invention comprises at least one silicone compound having a viscosity of less than 10,000,000 cSt at 25°C.
  • a silicone compound is advantageously chosen from silicone gums, volatile silicone oils and non-volatile silicone oils.
  • the care and/or makeup composition for the skin and/or the lips comprises at least one silicone compound.
  • compositions according to the invention make it possible to obtain compositions of which the deposit on keratin materials, and in particular on the skin and/or the lips, is not very tacky or not tacky at all. Its presence also makes it possible to improve the properties of transfer resistance of the deposits, and/or of resistance to attacks, in particular to rubbing.
  • the colour fastness of the deposits can also be improved (resistance to rubbing), as can the comfort and the cosmeticity of the deposit formed (softness, glidance to the touch of the deposit formed).
  • the silicone compound under consideration according to the invention may be a silicone oil having a viscosity of between 3 centistokes (cSt) (3 ⁇ 10 "6 m 2 /s) and 800 000 centistokes (cSt) (800 000 10 "6 m 2 /s).
  • the silicone compound under consideration according to the invention may be a non-volatile silicone oil having a viscosity of between 9 centistokes (cSt) (3 10 "6 m 2 /s) and 600 000 centistokes (cSt) (600 000 ⁇ 10 "6 m 2 /s).
  • silicon oil is intended to mean an oil comprising at least one silicon atom, and in particular at least one Si-O group.
  • the volatile or non-volatile silicone oils that can be used in the invention preferably have a viscosity at 25°C of less than 800 000 cSt, preferably less than or equal to 600 000 cSt, preferably less than or equal to 500 000 cSt.
  • the viscosity of these silicone oils can be measured according to standard ASTM D- 445.
  • composition according to the invention or under consideration according to a process of the invention can contain a mixture of silicone oils only partly made up of such an oil.
  • the silicone oils that can be used in the compositions of the invention may be vo- latile and/or non-volatile.
  • compositions according to the invention comprise at least one volatile silicone oil.
  • the volatile silicone oil that can be used in the invention can be chosen from silicone oils having in particular a viscosity ⁇ 8 centistokes (cSt) (8 ⁇ 10 "6 m 2 /s).
  • volatile silicone oil that can be used in the invention may be chosen preferably from silicone oils having a flash point ranging from 40°C to 102°C, pre- ferably having a flash point of greater than 55°C and less than or equal to 95°C, and preferentially ranging from 65°C to 95°C.
  • silicone oils in particular those having a viscosity ⁇ 8 centistokes (cSt) (8 x 10 "6 m 2 /s at 25°C), and especially having from 2 to 10 silicon atoms, and in particular from 2 to 7 silicon atoms, these silicones optionally comprising alkyl or alkoxy groups having from 1 to 10 carbon atoms.
  • cSt centistokes
  • volatile silicone oils are noncyclic and are in particular chosen from: - noncyclic linear silicones of formula (I): R3SiO-(R 2 SiO) n -SiR3 in which R, which may be identical or different, denotes:
  • a saturated or unsaturated hydrocarbon-based radical having from 1 to 10 carbon atoms, preferably from 1 to 6 carbon atoms, optionally substituted with one or more fluorine atoms or with one or more hydroxyl groups, or
  • one of the R radicals to be a phenyl group, n being an integer ranging from 0 to 8, preferably ranging from 2 to 6, and better still ranging from 3 to 5, the silicone compound of formula (I) containing at most 15 carbon atoms;
  • R which may be identical or different, denotes:
  • one of the R radicals to be a phenyl group, x being an integer ranging from 0 to 8, the silicone compound of formula (II) or (III) containing at most 15 carbon atoms.
  • the ratio between the number of carbon atoms and the number of silicon atoms is between 2.25 and 4.33.
  • the silicones of formulae (I) to (III) can be prepared according to known processes for synthesizing silicone compounds.
  • DC 200 Fluid 0.65 est by the company Dow Corning 1 ,3-di-tert-butyl-1 ,1 ,3,3-tetramethyldisiloxane
  • heptylpentamethyldisiloxane 1 ,1 ,1 -triethyl-3,3,3- trimethyldisiloxane
  • hexaethyldisiloxane 1 ,1 ,3,3-tetramethyl-1 ,3-bis(2- methylpropyl)disiloxane
  • pentamethyloctyldisiloxane 1 ,1 ,1 -trimethyl-3,3,3-tris(1 - methylethyl
  • DC 200 Fluid 1 est by the company Dow Corning
  • 3-pentyl-1 ,1 ,1 ,3,5,5,5-heptamethyltrisiloxane 1 -hexyl-1 ,1 ,3,3,5,5,5- heptamethyltrisiloxane; 1 ,1 ,1 ,3,3,5,5-heptamethyl-5-octyltrisiloxane; 1 ,1 ,1 ,3,5,5,5- heptamethyl-3-octyltrisiloxane, in particular sold under the name Silsoft 034 by the company OSI
  • DC 2-1731 by the company Dow Corning
  • DC 200 Fluid est 2 by the company Dow Corning
  • 1 ,1 ,3,3,5,5,7,7,9,9-decamethyl-1 ,9-dipropylpentasiloxane 3,3,5,5,7,7- hexaethyl-1 ,1 ,1 ,9,9,9-hexamethylpentasiloxane
  • 1 -butyl-1 ,1 ,3,3,5,5,7,7,9,9,9- undecamethylpentasiloxane 3,3-diethyl-1 ,1 ,1 ,5,5,7,7,9,9,9- decamethylpentasiloxane
  • hexasiloxanes 1 -butyl-1 ,1 ,3,3,5,5,7,7,9,9,1 1 ,1 1 ,1 1 - tridecamethylhexasiloxane; 3,5,7,9-tetraethyl-1 ,1 ,1 ,3,5,7,9,1 1 ,1 1 ,1 1 - decamethylhexasiloxane and tetradecamethylhexasiloxane;
  • tetrasiloxanes 2-[3,3,3-trimethyl-1 ,1 - bis[(trimethylsilyl)oxy]disiloxanyl]ethyl; 1 ,1 ,1 ,5,5,5-hexamethyl-3-(2-methylpropyl)- 3-[(trimethylsilyl)oxy]trisiloxane; 3-(1 ,1 -dimethylethyl)-1 ,1 ,1 ,5,5,5-hexamethyl-3- [(trimethylsilyl)oxy]trisiloxane; 3-butyl-1 ,1 ,1 ,5,5,5-hexamethyl-3-
  • pentasiloxanes 1 ,1 ,1 ,3,5, 5,7,7, 7-nonamethyl-3- (trimethylsiloxy)tetrasiloxane and 1 ,1 ,1 ,3,3,7,7,7-octamethyl-5-phenyl-5-[(trimethyl- silyl)oxy]tetrasiloxane;
  • hexasiloxanes 3,5-diethyl-1 ,1 ,1 ,7,7,7-hexamethyl-3,5- bis[(trimethylsilyl)oxy]tetrasiloxane and 1 ,1 ,1 ,3,5,7,7,7-octamethyl-3,5-bis- [(trimethylsilyl)oxy]tetrasiloxane;
  • heptasiloxane 1 ,1 ,1 ,3,7,7,7-heptamethyl-3,5,5- tris[(trimethylsilyl)oxy]tetrasiloxane;
  • octasiloxanes 1 ,1 ,1 ,3,5,5,9,9,9-nonamethyl-3,7,7- tris[(trimethylsilyl)oxy]pentasiloxane; 1 ,1 ,1 ,3,5,7,9,9,9-nonamethyl-3,5,7- tris[(trinnethylsilyl)oxy]pentasiloxane and 1 ,1 ,1 , 7,7, 7-hexamethyl-3, 3,5,5- tetrakis[(thmethylsilyl)oxy]tetrasiloxane.
  • decamethylcyclopentasiloxane in particular sold under the name DC-245 by the company Dow Corning
  • dodecamethylcydohexasiloxane in particular sold under the name DC-246 by the company Dow Corning
  • octamethyltrisiloxane in particular sold under the name DC-200 Fluid 1 est by the company Dow Corning
  • decamethyltetrasiloxane in particular sold under the name DC-200 Fluid 1 .5 cSt by the company Dow Corning and DC-200 Fluid 5 est sold by the company Dow Corning
  • octamethylcyclotetrasiloxane heptamethylhexyltrisiloxane, heptamethylethyltrisiloxane, heptamethyloctyltrisiloxane and dodecamethylpentasiloxane, and mixtures thereof.
  • linear oils prove to be particularly advantageous.
  • compositions according to the invention comprise at least one non-volatile silicone oil.
  • the non-volatile silicone oil that can be used in the invention may be chosen from silicone oils having a viscosity at 25°C of greater than or equal to 9 centistokes (cSt) (9 x 10 "6 m 2 /s) and less than 800 000 cSt, preferably between 50 and 600 000 cSt, preferably between 100 and 500 000 cSt.
  • the viscosity of this silicone can be measured according to standard ASTM D-445.
  • silicone oils two types of oils can be distinguished according to whether or not they are phenyl oils.
  • non-volatile linear silicone oils By way of representation of these non-volatile linear silicone oils, mention may be made of polydimethylsiloxanes; alkyl dimethicones; vinylmethyl methicones; and also silicones modified with aliphatic, optionally fluorinated, groups or with functional groups such as hydroxyl, thiol and/or amine groups.
  • non-phenyl, non-volatile silicone oils mention may be made of: - PDMSs comprising alkyl or alkoxy groups which are pendant and/or at the ends of the silicone chain, said groups each having from 2 to 24 carbon atoms, - PDMSs comprising aliphatic groups, or functional groups such as hydroxyl, thiol and/or amine groups,
  • a composition according to the invention contains at least one non-phenyl linear silicone oil.
  • the non-phenyl linear silicone oil may in particular be chosen from silicones of formula:
  • R1 , R2, R5 and R6 are, together or separately, an alkyl radical having 1 to 6 carbon atoms,
  • R3 and R4 are, together or separately, an alkyl radical having from 1 to 6 carbon atoms, a vinyl radical, an amine radical or a hydroxyl radical,
  • X is an alkyl radical having from 1 to 6 carbon atoms, a hydroxyl radical or an amine radical,
  • n and p being integers chosen so as to have a fluid compound.
  • non-volatile silicone oil that can be used according to the invention, mention may be made of those for which:
  • the substituents R1 to R6 and X represent a methyl group
  • p and n are such that the viscosity is 500,000 est, such as the product sold under the name SE30 by the company General Electric, the product sold under the name AK 500000 by the company Wacker, the product sold under the name Mirasil DM 500,000 by the company Bluestar and the product sold under the name Dow Corning 200 Fluid 500,000 est by the company Dow Corning;
  • the substituents R1 to R6 and X represent a methyl group, and p and n are such that the viscosity is 60,000 est, such as the product sold under the name Dow Corning 200 Fluid 60000 CS by the company Dow Corning and the product sold under the name Wacker Belsil DM 60,000 by the company Wacker;
  • the substituents R1 to R6 and X represent a methyl group, and p and n are such that the viscosity is 350 est, such as the product sold under the name Dow Corning 200 Fluid 350 CS by the company Dow Corning; - the substituents R1 to R6 represent a methyl group, the group X represents a hydroxyl group, and n and p are such that the viscosity is 700 est, such as the product sold under the name Baysilone Fluid TO.7 by the company Momentive.
  • a composition according to the invention contains at least one phenyl silicone oil.
  • the phenyl silicone oil comprises at least three phenyl groups, for example at least four, at least five or at least six;
  • R I R I R I (II) in which the R groups represent, independently of one another, a methyl or a phenyl, with the proviso that at least one R group represents a phenyl.
  • said organopolysiloxane comprises at least three phenyl groups, for example at least four or at least five. Mixtures of the phenyl organopolysiloxanes described above may be used. Mention may, for example, be made of mixtures of triphenyl, tetraphenyl or pentaphenyl organopolysiloxanes;
  • Me represents methyl
  • Ph phenyl
  • Such a phenyl silicone is in particular manufactured by Dow Corning under the reference PH-1555 HRI or else Dow Corning 555 Cosmetic Fluid (chemical name: 1 ,3,5-trimethyl 1 ,1 ,3,5,5- pentaphenyl trisiloxane; INCI name: trimethyl pentaphenyl trisiloxane).
  • Dow Corning 554 Cosmetic Fluid may also be used;
  • y ranges between 1 and 1000.
  • Use may, for example, be made of trimethyl siloxyphenyl dimethicone, in particular sold under the reference Belsil PDM 1000 by the company Wacker.
  • y is equal to 0.
  • Use may, for example, be made of phenyl trimethylsiloxy trisiloxane, in particular sold under the reference Dow Corning 556 Cosmetic Grade Fluid;
  • Ri to R10 are saturated or unsaturated, linear, cyclic or branched, C1 -C30 hydrocarbon-based radicals,
  • - m, n, p and q are, independently of one another, integers between 0 and 900, with the proviso that the sum 'm+n+q' is other than 0.
  • the sum 'm+n+q' is between 1 and 100.
  • the sum 'm+n+p+q' is between 1 and 900, even better still between 1 and 800.
  • q is equal to 0; - the phenyl silicone oils corresponding to the following formula (VII), and mixtures thereof:
  • R1 to R6 independently of one another, are saturated or unsaturated, linear, cyclic or branched, C1-C30 hydrocarbon-based radicals,
  • n and p are, independently of one another, integers between 0 and 100, with the proviso that the sum 'n + m' is between 1 and 100.
  • R1 to R6 independently of one another, represent a saturated, linear or branched, C1 -C30, in particular C1 -C12, hydrocarbon-based radical, and in particular a methyl, ethyl, propyl or butyl radical.
  • R1 to R6 may be identical, and in addition may be a methyl radical.
  • R1 to R6 may be identical, and in addition may be a methyl radical.
  • - R is a C1-C30 alkyl radical, an aryl radical or an aralkyl radical, - n is an integer ranging from 0 to 100, and
  • R radicals of formula (VIII), and Ri to Rio defined above can each represent a linear or branched, saturated or unsaturated, especially C2-C20, in particular C3-C16 and more particularly C4-C10, alkyl radical, or a C6-Ci 4 , in particular C10-C13, monocyclic or polycyclic aryl radical, or an aralkyl radical, the aryl and alkyl residues of which are as defined above.
  • R of formula (VIII) and Ri to R10 can each represent a methyl, ethyl, propyl, isopropyl, decyl, dodecyl or octadecyl radical, or else a phenyl, tolyl, benzyl or phenethyl radical.
  • a phenyl silicone oil of formula (VIII) having a viscosity at 25°C of between 5 and 1500 mm 2 /s (i.e. 5 to 1500 cSt), preferably having a viscosity between 5 and 1000 mm 2 /s (i.e. 5 to 1000 cSt).
  • phenyl silicone oil of formula (VIII) use may in particular be made of phenyl trimethicones, such as DC556 from Dow Corning (22.5 cSt) or the Silbione 70663V30 oil from Rhone Poulenc (28 cSt), or diphenyl dimethicones, such as the Belsil oils, in particular Belsil PDM1000 (1000 cSt), Belsil PDM 200 (200 cSt) and Belsil PDM 20 (20 cSt) from Wacker.
  • the values between parentheses represent the viscosities at 25°C; - phenyl silicone oils corresponding to the following formula, and mixtures thereof:
  • R1 , R2, R5 and R6 are, together or separately, an alkyl radical having 1 to 6 carbon atoms,
  • R3 and R 4 are, together or separately, an alkyl radical having from 1 to 6 carbon atoms, or an aryl radical,
  • X is an alkyl radical having from 1 to 6 carbon atoms, a hydroxyl radical or a vinyl radical,
  • n and p being chosen so as to give the oil a weight-average molecular weight of less than 200 000 g/mol, preferably less than 150 000 g/mol and more preferably less than 100 000 g/mol.
  • the phenyl silicones that are more particularly suitable for the invention are those corresponding to formulae (II) (and in particular formula (III)), and (V), above.
  • the phenyl silicones are chosen more from phenyl trimethicones, phenyl dimethicones, phenyltrimethylsiloxydiphenylsiloxanes, diphenyl dimethicones, diphenylmethyldiphenyltrisiloxanes and 2- phenylethyltrimethylsiloxysilicat.es, and mixtures thereof.
  • the weight-average molecular weight of the non-volatile phenyl silicone oil according to the invention ranges from 500 to 10 000 g/mol.
  • a composition according to the invention contains at least one silicone gum.
  • the silicone gum that can be used in the invention may be chosen from silicone gums having a viscosity at 25°C of greater than 800,000 centistokes (cSt) (9 x 10 "6 m 2 /s) and in particular between 800,000 and 10,000,000 cSt, preferably between 1 ,000,000 and 5,000,000 cSt, preferably between 1 ,000,000 and 2,500,000 cSt.
  • the viscosity of this silicone can be measured according to standard ASTM D-445.
  • the molecular weight of the silicone gums is generally greater than 350,000 g/mol, between 350,000 and 800,000 g/mol, preferably from 450,000 to 700,000 g/mol
  • the silicone gum may in particular be chosen from the silicones of the formula:
  • R1 , R2, R5 and R6 are, together or separately, an alkyl radical having 1 to 6 carbon atoms,
  • R3 and R4 are, together or separately, an alkyl radical having from 1 to 6 carbon atoms, a vinyl radical, an amine radical or a hydroxyl radical,
  • X is an alkyl radical having from 1 to 6 carbon atoms, a hydroxyl radical or an amine radical,
  • n and p being integers chosen such that the viscosity of the compound is greater than 800,000 cSt.
  • silicone gum that can be used according to the invention, mention may be made of those for which:
  • the substituents R1 to R6 represent a methyl group
  • the group X represents a methyl group
  • n and p are such that the molecular weight of the polymer is 600 000 g/mol, such as the product sold under the name Mirasil C-DPDM by the company Bluestar;
  • the substituents R1 to R6 represent a methyl group
  • the group X represents a hydroxyl group
  • n and p are such that the molecular weight of the polymer is
  • a composition according to the invention may comprise from 0.1 % to 60% by weight of silicone compound(s) according to the invention, relative to the total weight of the composition.
  • silicone compound(s) according to the invention may comprise from 0.2% to 50% by weight of silicone compound(s) according to the invention, relative to the total weight of the composition.
  • silicone compound(s) according to the invention may comprise from 0.5% to 40% by weight of silicone compound(s) according to the invention, relative to the total weight of the composition.
  • a composition according to the invention may also comprise at least one solid fatty substance, in particular chosen from waxes and/or pasty fatty substances.
  • the amount of pasty substance in the makeup and/or care composition according to the invention is between 0.5% and 50% by weight, in particular 1 % to 40% by weight, or even 2% to 30% by weight, relative to the total weight of the composition.
  • the composition is free of wax.
  • the composition comprises at least one wax.
  • the amount of wax(es) in the makeup and/or care composition according to the invention can preferably range from 0.1 % to 70% by weight, relative to the total weight of the composition, preferably from 1 % to 40% by weight, and better still from 5% to 30% by weight.
  • the wax content is between 0.5% and 30% by weight, in particular 1 % to 20% by weight, or even 2% to 15% by weight, relative to the total weight of the composition.
  • wax is intended to mean a lipophilic compound that is solid at ambient temperature (25°C), with a solid/liquid reversible change of state, having a melting point of greater than or equal to 30°C, which may be up to 200°C.
  • the waxes may be chosen from waxes of animal, plant, mineral or synthetic origin and mixtures thereof.
  • Mention may in particular be made of hydrocarbon-based waxes, for instance beeswax, lanolin wax and Chinese insect waxes; rice bran wax, Carnauba wax, Candelilla wax, Ouricury wax, Alfalfa wax, berry wax, shellac wax, Japan wax and sumach wax; montan wax, orange wax and lemon wax, microcrystalline waxes, paraffins and ozokerite; polyethylene waxes, waxes obtained by Fischer-Tropsch synthesis and waxy copolymers, and also esters thereof. Mention may also be made of waxes obtained by catalytic hydrogenation of animal or plant oils having linear or branched C8-C32 fatty chains. Among these, mention may in particular be made of hydrogenated sunflower oil, hydrogenated castor oil, hydrogenated coconut oil, hydrogenated lanolin oil and bis(1 ,1 ,1 - trimethylolpropane) tetrastearate.
  • hydrocarbon-based waxes for instance beeswax,
  • silicone waxes and of fluoro waxes Use may also be made of waxes obtained by hydrogenation of castor oil esterified with cetyl alcohol.
  • composition according to the invention may comprise at least one wax which is in particular hydrocarbon-based.
  • the composition is free of pasty fatty substances.
  • the composition comprises at least one pasty fatty substance.
  • the amount of pasty fatty substance in the makeup and/or care composition according to the invention is preferably between 0.5% and 30% by weight, in particular 1 % to 20% by weight, or even 2% to 15% by weight, relative to the total weight of the composition.
  • pasty fatty substance is intended to mean a lipophilic fatty compound with a reversible solid/liquid change of state and comprising a liquid fraction and a solid fraction at a temperature of 23°C.
  • the pasty compound preferably has a hardness at 20°C ranging from 0.001 to 0.5 MPa, preferably from 0.002 to 0.4 MPa.
  • the pasty compound is preferably chosen from synthetic compounds and compounds of plant origin. A pasty compound can be obtained by synthesis from starting products of plant origin. Mention may in particular be made, alone or as a mixture, of:
  • lanolin and derivatives thereof, such as lanolin alcohol, oxyethylenated lanolins, acetylated lanolin, lanolin esters such as isopropyl lanolate, or oxypropylenated lanolins,
  • - polymeric or non-polymeric silicone compounds having a viscosity of greater than 10,000,000 cSt at 25°C, for instance high-molecular-weight polydimethylsiloxanes, polydimethylsiloxanes with side chains of the alkyl or alkoxy type having from 8 to 24 carbon atoms, in particular stearyl dimethicones,
  • - vinyl polymers in particular olefin homopolymers; olefinic copolymers; hydrogenated diene homopolymers and copolymers; linear or branched homopolymer or copolymer oligomers of alkyl (meth)acrylates preferably containing a C8-C30 alkyl group; homopolymer and copolymer oligomers of vinyl esters containing C8-C30 alkyl groups; homopolymer and copolymer oligomers of vinyl ethers containing C8-C30 alkyl groups,
  • - liposoluble polyethers resulting from polyetherification between one or more C2- C100, preferably C2-C50, diols; and in particular copolymers of ethylene oxide and/or of propylene oxide with C6-C30 long-chain alkylene oxides, more preferably such that the weight ratio of the ethylene oxide and/or propylene oxide to the alkylene oxides in the copolymer is from 5:95 to 70:30,
  • - polyol ethers chosen from ethers of pentaerythritol and of polyalkylene glycol, ethers of fatty alcohol and of sugar, and mixtures thereof, the ether of pentaerythritol and of polyethylene glycol comprising 5 oxyethylene (5 OE) units (CTFA name: PEG-5 pentaerythityl ether), and the ether of pentaerythritol and of polypropylene glycol comprising 5 oxypropylene (5 OP) units (CTFA name: PPG-5 pentaerythrityl ether), and mixtures thereof;
  • esters and polyesters and in particular (i) the esters of a glycerol oligomer, especially diglycerol esters, in particular condensates of adipic acid and of glycerol, for which some 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; (ii) phytosterol esters, (iii) pentaerythritol esters; (iv) esters formed from at least one alcohol, at least one of the alcohols being a Guerbet alcohol, and of a diacid dimer formed from at least one unsaturated fatty acid; (v) non-croslinked polyesters resulting from polycondensation between a linear or branched C 4 -C 5 o dicarboxylic acid or polycarboxylic acid and a C2-C50 diol or
  • the aliphatic hydroxycarboxylic acid ester is advantageously derived from a hydroxylated aliphatic carboxylic acid containing 2 to 40 carbon atoms and 1 to 20 hydroxyl groups; (viii) aliphatic esters of an ester, chosen from the ester resulting from the esterification reaction of hydrogenated castor oil with isostearic acid (hydrogenated castor oil monoisostearate, diisostearate or triisostearate).
  • the pasty compound may also be of plant origin. Mention may in particular be made of isomerized jojoba oil, such as trans-isomerized, partially hydrogenated jojoba oil; orange wax, shea butter, partially hydrogenated olive oil, cocoa butter and mango oil.
  • the composition according to the invention may also comprise one or more dyestuffs chosen from pulverulent compounds, for instance pigments, pearlescent agents and glitter flakes, and/or liposoluble or water-soluble dyes.
  • the dyestuffs in particular pulverulent dyestuffs, may be present in the composition in a content of from 0.01 % to 50% by weight, relative to the weight of the composition, preferably from 0.1 % to 40% by weight, or even from 1 % to 30% by weight.
  • pigments should be understood to mean white or coloured, mineral or organic particles of any shape, which are insoluble in the physiological medium, and which are intended to colour the composition.
  • pearlescent agents should be understood to mean iridescent particles of any shape, in particular produced by certain molluscs in their shell, or alternatively synthesized.
  • the pigments may be white or coloured, mineral and/or organic, and interference or non-interference.
  • mineral pigments mention may be made of titanium dioxide, optionally surface-treated, zirconium oxide or cerium oxide, and also iron oxide, chromium oxide, manganese violet, ultramarine blue, chromium hydrate and ferric blue.
  • organic pigments mention may be made of carbon black, pigments of D & C type, and lakes based on cochineal carmine, or on barium, strontium, calcium or aluminium.
  • the pearlescent pigments may be chosen from white pearlescent pigments such as mica coated with titanium or with bismuth oxychloride, coloured pearlescent pigments such as titanium mica with iron oxides, titanium mica with in particular ferric blue or with chromium oxide, titanium mica with an organic pigment of the abovementioned type, and also pearlescent pigments based on bismuth oxychloride.
  • the water-soluble dyes are, for example, beetroot juice and methylene blue and can represent 0.01 % to 6% of the total weight of the composition.
  • the composition comprises at least one dyestuff.
  • the dyestuff is in particular chosen from organic or inorganic dyestuffs, in particular of the type of pigments or pearlescent agents conventionally used in cosmetic compositions, liposoluble or water-soluble dyes, materials with a specific optical effect, and mixtures thereof.
  • the amount of dyestuff(s) in a composition according to the invention is between 0.01 % and 40% by weight, in particular 0.1 % and 30% by weight, or even 1 % and 20% by weight, of the total weight of the composition.
  • a composition according to the invention in particular a care and/or makeup composition for the skin and/or the lips, comprises at least one organic or inorganic filler.
  • it will be a sebum-absorbing filler in the case of a makeup composition for the skin or a silicone filler, in particular in the case of a makeup composition for the lips.
  • a filler makes it possible in particular to reduce the tack of the deposit when it is applied and while wearing it.
  • compositions in particular makeup compositions, of which the deposit on keratin materials, and in particular the lips and/or the skin, is uniform and/or not very tacky or not at all tacky.
  • Such a deposit can in particular provide a feeling of comfort while being worn (softness, property of glidance of the deposit formed).
  • such a composition may have transfer resistance properties and also properties of colour fastness of the deposit (no fragility or fragmentation of the deposit, which remains uniform, and resistant to rubbing), and of staying power with respect to grease.
  • composition according to the invention may also comprise at least one organic or inorganic filler.
  • a composition may comprise from 0.01 % to 35% by weight, preferably 0.1 % to 20% by weight of filler(s), relative to its total weight.
  • talc talc
  • silica kaolin
  • calcium carbonate barium sulphate
  • nylon powders in particular Orgasol
  • polyethylene powders teflon, starch, boron nitride, copolymer microspheres such as Expancel (Nobel Industrie); and also mixtures thereof.
  • a composition according to the invention contains at least one filler capable of absorbing an oil .
  • a composition according to the invention comprises at least one filler which has a capacity to absorb and/or adsorb an oil or a liquid fatty substance such as, for example, sebum (of the skin).
  • This oil-absorbing filler may also advantageously have a BET specific surface area greater than or equal to 300 m 2 /g, preferably greater than 500 m 2 /g, and preferentially greater than 600 m 2 /g, and in particular less than 1500 m 2 /g.
  • the "BET specific surface area” is determined according to the BET (Brunauer - Emmet - Teller) method described in "The journal of the American Chemical Society", vol. 60, page 309, February 1938 and corresponding to international standard ISO 5794/1 (annex D).
  • the BET specific surface area corresponds to the total specific surface area (therefore including micropores) of the powder.
  • the filler under consideration according to the invention is thus characterized in that it has an oil uptake of greater than or equal to 1 ml/g, in particular ranging from 1 ml/g to 20 ml/g, or even ranging from 1 .5 ml/g to 15 ml/g.
  • it has an oil uptake of greater than or equal to 2 ml/g, in particular ranging from 2 ml/g to 20 ml/g, or even ranging from 2 ml/g to 15 ml/g.
  • This oil uptake which corresponds to the amount of oil absorbed and/or adsorbed by the filler, can be characterized by measuring the wet point according to the method described hereinafter.
  • the oil uptake of a powder is measured according to the method for determining oil uptake of a powder descrbed in standard NF T 30-022. It corresponds to the amount of oil adsorbed onto the available surface of the pulverulent material by measurement of the wet point.
  • isononyl isononanoate is incorporated into the filler using a spatula and isononyl isononanoate continues to be added until the formation of conglomerates of isononyl isononanoate and of powder. From this moment on, isononyl isononanoate is added one drop at a time and the mixture is then triturated with the spatula. The addition of isononyl isononanoate is stopped when a smooth firm paste is obtained. It should be possible to spread this paste over the glass plate without there being any cracks or any formation of lumps. The volume Vs (expressed in ml) of isononyl isononanoate used is then noted.
  • the oil uptake corresponds to the Vs/m ratio.
  • This oil-absorbing filler may be a mineral powder or an organic powder; it may be chosen from silica, polyamide (nylon®) powders, powders of acrylic polymers, in particular of polymethyl methacrylate, or of polymethyl methacrylate/ethylene glycol dimethacrylate, of polyallyl methacrylate/ethylene glycol dimethacrylate, of ethylene glycol dimethacrylate/lauryl methacrylate copolymer; silicone elastomer powders, in particular obtained by polymerization of organopolysiloxane having at least two hydrogen atoms each bonded to a silicon atom and of an organopolysiloxane comprising at least two ethylenically unsaturated groups (in particular two vinyl groups) in the presence of a platinum catalyst.
  • silica polyamide (nylon®) powders
  • powders of acrylic polymers in particular of polymethyl methacrylate, or of polymethyl methacrylate/ethylene glycol dimethacrylate, of polyallyl me
  • the oil-absorbing filler may be a powder coated with a hydrophobic treatment agent.
  • fillers having an oil uptake of greater than or equal to 1 .5 ml/g are described below, with their oil uptake value measured according to the protocol defined above.
  • silica powders mention may be made of:
  • silica microspheres in particular those sold under the name Sunsphere® H53, Sunsphere® H33 (oil uptake equal to 3.70 ml/g) by the company Asahi Glass; MSS-500-3H by the company Kobo; Silica Beads SB-700 by the company Myoshi;
  • silica silylate powders in particular those sold under the name Dow Corning VM- 2270 Aerogel Fine Particles by the company Dow Corning (oil uptake equal to
  • silica particles in particular those sold under the name Silica Shells by the company Kobo (oil uptake equal to 5.50 ml/g);
  • precipitated silica powders surface-treated with a mineral wax such as precipitated silica treated with a polyethylene wax, and in particular those sold under the name Acematt OR 412 by the company Evonik Degussa (oil uptake equal to 3.98 ml/g).
  • acrylic polymer powders mention may be made of: - porous spheres of polymethyl methacrylate/ethylene glycol dimethacrylate, sold under the name Microsponge 5640 by the company Cardinal Health technologies (oil uptake equal to 1 .55 ml/g), Ganzpearl® GMP-0820 by the company Ganz Chemical;
  • polyamide powders mention may be made of:
  • magnesium carbonate powder mention may in particular be made of the product sold under the name Tipo Carbomagel by the company Buschle & Lepper (oil uptake equal to 2.14 ml/g).
  • the oil-absorbing filler which is particularly preferred is a silica powder and more particularly a silica powder having an oil uptake at least equal to 3.70 ml/g, and in particular those sold under the name Sunsphere® H 33 by the company Asahi Glass, and under the name Dow Corning VM-2270 Aerogel Fine Particles by the company Dow Corning.
  • the filler(s) in particular capable of absorbing an oil may be present in a composition according to the invention in a content ranging from 0.5% to 40% by weight, preferably from 1 % to 20% by weight, and better still from 1 % to 15% by weight, relative to the total weight of the composition.
  • a composition according to the invention may use at least one filler and at least one supramolecular polymer in a polymer(s)/oil-absorbing filler(s) weight ratio of greater than 1 , preferably greater than 1 .5, and even better still greater than 2.
  • a composition according to the invention contains at least one filler having an oil uptake of greater than or equal to 1 .5 ml/g.
  • compositions according to the invention may comprise at least one silicone filler.
  • the silicone filler may be chosen from silicone-resin-coated organopolysiloxane powders and polymethylsilsesquioxane powders, and mixtures thereof.
  • the organopolysiloxane powder may in particular be coated with silsesquioxane resin, as described, for example, in patent US 5 538 793.
  • silsesquioxane resin as described, for example, in patent US 5 538 793.
  • Such elastomer powders are sold under the names KSP-100, KSP-101 , KSP-102, KSP-103, KSP-104 and KSP-105 by the company Shin Etsu, and have the INCI name: vinyl dimethicone/methicone silsesquioxane crosspolymer.
  • silicone resin microbeads such as those sold under the name Tospearl by the company Momentive Performance Materials, and in particular under the reference Tospearl 145 A; and mixtures thereof.
  • composition according to the invention may comprise a silicone filler chosen from silicone-resin-coated organopolysiloxane powders and polymethylsilsesquioxane powders.
  • a composition according to the invention in particular a makeup composition for the skin and/or the lips, may comprise at least one silicone elastomer, otherwise known as organopolysiloxane elastomer.
  • organopolysiloxane elastomer is intended to mean a supple, deformable organopolysiloxane having viscoelastic properties and in particular the consistency of a sponge or of a supple sphere. Its modulus of elasticity is such that this material withstands deformation and has a limited capacity for extension and contraction. This material is capable of retaining its original shape after having been stretched.
  • the organopolysiloxane elastomer is obtained by crosslinking addition reaction (A) of diorganopolysiloxane containing at least two hydrogens each bonded to a silicon, and (B) of diorganopolysiloxane having at least two ethylenically unsaturated groups bonded to silicon, in particular in the presence (C) of a platinum catalyst, as described, for example, in application EP-A-295886.
  • the organopolysiloxane elastomer can be obtained by reaction of dimethylpolysiloxane containing dimethylvinylsiloxy end groups and of methylhydrogenopolysiloxane containing trimethylsiloxy end groups, in the presence of a platinum catalyst.
  • Compound (A) may in particular be chosen from methylhydrogenopolysiloxanes containing trimethylsiloxy end groups, dimethylsiloxane-methylhydrogenosiloxane copolymers containing trimethylsiloxy end groups and dimethylsiloxane- methylhydrogenosiloxane cyclic copolymers.
  • the organopolysiloxanes (B) may in particular be chosen from methylvinylpolysiloxanes, methylvinylsiloxane-dimethylsiloxane copolymers, dimethylpolysiloxanes containing dimethylvinylsiloxy end groups, dimethyl- siloxane-methylphenylsiloxane copolymers containing dimethylvinylsiloxy end groups, dimethylsiloxane-diphenylsiloxane-methylvinylsiloxane copolymers containing dimethylvinylsiloxy end groups, dimethylsiloxane-methylvinylsiloxane copolymers containing trimethylsiloxy end groups, dimethylsiloxane-methylphenyl- siloxane-methylvinylsiloxane copolymers containing trimethylsiloxy end groups, methyl(3,3,3-trifluoropropyl)polysiloxane containing dimethyl
  • compound (A) is added in an amount such that the molecular ratio between the total amount of hydrogen atoms bonded to silicon atoms in compound (A) and the total amount of all the ethylenically unsaturated groups in compound (B) is within the range of from 1 .5/1 to 20/1 .
  • Compound (C) is the catalyst for the crosslinking reaction, and is in particular chloroplatinic acid, chloroplatinic acid-olefin complexes, chloroplatinic acid- alkenylsiloxane complexes, chloroplatinic acid-diketone complexes, platinum black or platinum on a support.
  • the catalyst (C) is preferably added at from 0.1 to 1000 parts by weight, better still 1 to 100 parts by weight, as plain platinum metal per 1000 parts by weight of the total amount of compounds (A) and (B).
  • the elastomer is advantageously a non-emulsifying elastomer.
  • non-emulsifying defines organopolysiloxane elastomers that do not contain any hydrophilic chains, and in particular that do not contain any polyoxyalkylene units (especially polyoxyethylene or polyoxypropylene), or any polyglyceryl units.
  • the organopolysiloxane elastomer particles are conveyed in the form of a gel consisting of an elastomeric organopolysiloxane included in at least one hydrocarbon-based oil and/or one silicone oil. In these gels, the organopolysiloxane particles are often non-spherical particles.
  • Non-emulsifying elastomers are in particular described in patents EP 242 219, EP 285 886 and EP 765 656 and in application JP-A-61 -194009, the content of which is incorporated by way of reference.
  • Spherical non-emulsifying elastomers that may be used include those sold under the names DC 9040, DC 9041 , DC 9509, DC 9505 and DC 9506 by the company Dow Corning.
  • organopolysiloxane elastomers with an MQ group such as those sold by the company Wacker under the names Belsil RG100, Belsil RPG33 and preferentially RG80.
  • the elastomer may also be an emulsifying elastomer.
  • emulsifying organopolysiloxane elastomer is intended to mean an organopolysiloxane elastomer comprising at least one hydrophilic chain, such as polyoxyalkylenated organopolysiloxane elastomers and polyglycerolated silicone elastomers.
  • the emulsifying organopolysiloxane elastomer may be chosen from polyoxyalkylenated organopolysiloxane elastomers.
  • the polyoxyalkylenated organopolysiloxane elastomer is a crosslinked organopolysiloxane elastomer which can be obtained by means of a crosslinking addition reaction of diorganopolysiloxane containing at least one hydrogen bonded to silicon and of a polyoxyalkylene containing at least two ethylenically unsaturated groups.
  • the polyoxyalkylenated organopolysiloxane elastomers may be formed from divinyl compounds, in particular polyoxyalkylenes containing at least two vinyl groups, which react with Si-H bonds of a polysiloxane.
  • Polyoxyalkylenated organopolysiloxane elastomers that can be used include those sold under the names KSG-21 , KSG-20, KSG-30, KSG-31 , KSG-32, KSG-33, KSG-210, KSG-310, KSG-320, KSG-330 and KSG-340 by the company Shin Etsu, and DC9010 and DC901 1 by the company Dow Corning.
  • Emulsifying organopolysiloxane elastomer may also be chosen from polyglycerolated organopolysiloxane elastomers.
  • the polyglycerolated organopolysiloxane elastomer according to the invention is an organopolysiloxane elastomer which can be obtained by means of a crosslinking addition reaction of diorganopolysiloxane containing at least one hydrogen bonded to silicon and of polyglycerolated compounds having ethylenically unsaturated groups, in particular in the presence of a platinum catalyst.
  • the polyglycerolated organopolysiloxane elastomer according to the invention is conveyed in the form of a gel in at least one hydrocarbon-based oil and/or one silicone oil.
  • the polyglycerolated elastomer is often in the form of non-spherical particles.
  • Polyglycerolated organopolysiloxane elastomers that may be used include those sold under the names KSG-710, KSG-810, KSG-820, KSG-830 and KSG-840 by the company Shin Etsu.
  • Non-emulsifying elastomers that can more particularly be used include those sold under the names KSG-6, KSG-15, KSG-16, KSG-18, KSG-41 , KSG-42, KSG-43 and KSG-44 by the company Shin Etsu, DC9040 and DC9041 by the company Dow Corning and SFE 839 by the company General Electric.
  • Emulsifying elastomers that can more particularly be used include those sold under the names KSG-31 , KSG-32, KSG-33, KSG-210 and KSG-710 by the company Shin Etsu.
  • the organopolysiloxane elastomer under consideration according to the invention is chosen from spherical, non-emulsifying organopolysiloxane elastomers, polyglycerolated organopolysiloxane elastomers and polyoxyalkylenated organopolysiloxane elastomers.
  • composition according to the invention may comprise an organopolysiloxane elastomer, alone or as a mixture, in a content ranging from 0.1 % to 20% by weight, preferably from 0.2% to 15% by weight, and even more preferably from 0.5% to
  • the composition may also comprise other ingredients commonly used in cosmetic compositions. Such ingredients may be chosen from water, hydrophilic solvents, antioxidants, fragrances, essential oils, preservatives, cosmetic active agents, moisturizers, vitamins, ceramides, sunscreens, surfactants, gelling agents, thickeners, spreading agents, wetting agents, dispersants, antifoams, neutralizing agents, stabilizers, polymers and in particular film-forming polymers, and mixtures thereof. Of course, those skilled in the art will take care to select this or these optional additional ingredient(s) and the amount thereof in such a way that the advantageous properties of the composition are not, or not substantially, impaired by the addition envisaged.
  • film-forming polymers use may especially be made of a film-forming polymer in particular chosen from polyamide silicone block polymers, block ethylenic polymers, vinyl polymers comprising at least one carbosiloxane dendrimer derivative, copolymers comprising carboxylate groups and polydimethylsiloxane groups, silicone resins and lipodispersible polymers in the form of a non-aqueous dispersion of particles of polymers and mixtures thereof.
  • a film-forming polymer in particular chosen from polyamide silicone block polymers, block ethylenic polymers, vinyl polymers comprising at least one carbosiloxane dendrimer derivative, copolymers comprising carboxylate groups and polydimethylsiloxane groups, silicone resins and lipodispersible polymers in the form of a non-aqueous dispersion of particles of polymers and mixtures thereof.
  • the film-forming polymer may be chosen from the group comprising: - a block ethylenic copolymer (also called block ethylenic polymer), containing at least one first block having a glass transition temperature (Tg) of greater than or equal to 40°C and being totally or partially derived from one or more first monomers, which are such that the homopolymer prepared from these monomers has a glass transition temperature of greater than or equal to 40°C, and at least one second block having a glass transition temperature of less than or equal to 20°C and being totally or partially derived from one or more second monomers, which are such that the homopolymer prepared from these monomers has a glass transition temperature of less than or equal to 20°C, said first block and said second block being connected to one another via a random intermediate segment comprising at least one of said first constituent monomers of the first block and at least one of said second constituent monomers of the second block, and said block copolymer having a polydispersity index I of greater than 2, as described in
  • a vinyl polymer comprising at least one unit derived from a carbosiloxane dendrimer, as described in applications WO03/045337 and EP 963 751 from the company Dow Corning,
  • R 4 , R 5 , R 6 and R 7 which may be identical or different, represent a group chosen from:
  • Ci to C 4 o hydrocarbon- based groups which can contain, in their chain, one or more oxygen, sulphur and/or nitrogen atoms, and which can be partially or totally substituted with fluorine atoms,
  • Cio aryl groups optionally substituted with one or more Ci to C 4 alkyl groups,
  • polyorganosiloxane chains optionally containing one or more oxygen, sulphur and/or nitrogen atoms,
  • the X which may be identical or different, represent a linear or branched Ci to C30 alkylenediyl group, which can contain, in its chain, one or more oxygen and/or nitrogen atoms,
  • Y is a C1-C50, saturated or unsaturated, arylalkylene, alkylarylene, cycloalkylene, arylene, linear or branched alkylene divalent group which can comprise one or more oxygen, sulphur and/or nitrogen atoms, and/or can bear, as substituent one of the following atoms or groups of atoms: fluorine, hydroxyl, C3 to Cs cycloalkyl, Ci to C 4 o alkyl, C 5 to C10 aryl, phenyl optionally substituted with 1 to 3 Ci to C3 alkyl, Ci to C3 hydroxyalkyl and Ci to Ce aminoalkyl groups, or
  • Y represents a group corresponding to the formula: in which:
  • T represents a linear or branched, saturated or unsaturated, C3 to C2 4 trivalent or tetravalent hydrocarbon-based group optionally substituted with a polyorganosiloxane chain, and which can contain one or more atoms chosen from O, N and S, or T represents a trivalent atom chosen from N, P and Al, and
  • R 8 represents a linear or branched Ci to C50 alkyl group, or a polyorganosiloxane chain, which can comprise one or more ester, amide, urethane, thiocarbamate, urea, thiourea and/or sulphonamide groups, which may possibly be linked to another chain of the polymer,
  • n is an integer ranging from 2 to 500, preferably from 2 to 200
  • m is an integer ranging from 50 to 1000, preferably from 50 to 700 and even better still from 50 to 200; as described in application PCT/FR2009/052388, incorporated by way of reference,
  • silicone resins in particular chosen from polymethylsilsesquioxanes, siloxysilicate resins, in particular trimethylsiloxysilicate resins, as described in application FR0954344, incorporated by way of reference,
  • a copolymer comprising carboxylate groups and polydimethylsiloxane groups in particular chosen from copolymers of acrylic acid and of stearyl acrylate comprising polydimethylsiloxane grafts, copolymers of stearyl methacrylate comprising polydimethylsiloxane grafts, copolymers of acrylic acid and of stearyl methacrylate comprising polydimethylsiloxane grafts, copolymers of methyl methacrylate, of butyl methacrylate, of 2-ethylhexyl acrylate and of stearyl methacrylate comprising polydimethylsiloxane grafts,
  • compositions according to the invention may in particular make it possible to improve the grease resistance (staying power with respect to grease) of the deposits formed with these compositions on keratin materials, in particular such as the skin and/or the lips, improves the staying power, in particular the colour fastness, of the deposit (resistance to rubbing), and makes it possible to obtain a deposit which is not very tacky or not at all tacky.
  • the compositions according to the invention may be in any form which is acceptable and customary for a cosmetic composition.
  • They may therefore be in the form of a suspension, a dispersion, in particular of oil in water by virtue of vesicles, or water in oil; an aqueous, organic or oily solution which is optionally thickened or even gelled; an oil-in-water, water-in-oil or multiple emulsion; a gel, in particular an aqueous, oily or emulsified gel; a foam; a dispersion of vesicles, in particular lipid vesicles; a two-phase or multiphase lotion; a spray; a lotion, a cream, an ointment, a soft paste, a salve, a solid which has been cast or moulded, in particular as a stick or in a dish, or a compacted solid.
  • a composition according to the invention may also comprise an aqueous phase, which may represent 1 % to 80% by weight, in particular 2% to 70% by weight, or even 3% to 60% by weight, of the total weight of the composition.
  • This aqueous phase may consist essentially of water, or may comprise a mixture of water and of a water-miscible solvent (miscibility in water greater than 50% by weight at 25°C) in particular chosen from monoalcohols containing 1 to 5 carbon atoms, such as ethanol or isopropanol, glycols containing 2 to 8 carbon atoms, such as propylene glycol, ethylene glycol, 1 ,3-butylene glycol or dipropylene glycol, C3-C 4 ketones, C2-C 4 aldehydes, and mixtures thereof.
  • compositions according to the invention are advantageously anhydrous.
  • the composition used according to the invention is anhydrous or contains less than 3% by weight of water, preferably less than 1 % by weight of water, relative to the total weight of the composition.
  • the composition is preferably anhydrous.
  • compositions according to the invention can be used for caring for or making up keratin materials such as the skin, the eyelashes, the eyebrows, the nails, the lips, the hair, and more particularly for making up the lips, the hair, the eyelashes and/or the face.
  • a care and/or makeup product for the skin of the body or of the face, the lips, the eyelashes, the eyebrows, the hair or the nails; of an antisun or self-tanning product; or of a hair product; they are advantageously in the form of a makeup composition, in particular a mascara, eyeliner, lipstick, lip gloss, face powder, eye shadow, foundation, nail varnish or hair mascara composition.
  • the composition in the case of a lipstick, may be in liquid (gloss) or solid form, for example such as a lipstick in the form of a stick or cast in a dish.
  • the compositions according to the invention may be in solid or liquid form at 20°C.
  • the term "solid” characterizes the state of the composition at a temperature of 20°C.
  • a solid composition according to the invention has, at a temperature of 20°C and at atmospheric pressure (760 mmHg), a hardness of greater than 30 Nm "1 , preferably greater than 40 Nm "1 .
  • composition in particular such as a stick of a lipstick, is measured according to the following protocol:
  • the stick is stored at 20°C for 24 hours before measuring the hardness.
  • the hardness may be measured at 20°C via the "cheese wire” method, which consists in transversely cutting a wand of product, which is preferably a circular cylinder, by means of a rigid tungsten wire 250 ⁇ in diameter, by moving the wire relative to the stick at a speed of 100 mm/min.
  • the hardness of the samples of compositions of the invention is measured by means of a DFGS2 dynamometer sold by the company Indelco- Chatillon.
  • the measurement is reproduced three times and then averaged.
  • the average of the three values read using the dynamometer mentioned above, denoted Y, is given in grams. This average is converted to newtons and then divided by L which represents the longest distance through which the wire passes. In the case of a cylindrical wand, L is equal to the diameter (in metres).
  • a solid composition according to the invention has a hardness at 20°C of greater than or equal to 30 Nm "1 , preferably greater than 40 Nm "1 , preferably greater than 50 Nm "1 .
  • the composition according to the invention has in particular a hardness at 20°C of less than 500 Nm "1 , in particular less than 400 Nm "1 , preferably less than 300 Nm "1 .
  • a composition of which the hardness is greater than 30 Nm "1 is a "solid" composition at 20°C and at atmospheric pressure (760 mmHg).
  • compositions according to the invention find their most particular use in the field of lipsticks and foundations, compositions which are particularly sensitive to grease (sebum and food grease).
  • Another subject of the invention is a cosmetic treatment process for keratin materials, in particular the skin of the body or of the face, the lips, the nails, the eyelashes, and/or the hair, comprising the application, to said materials, of a cosmetic composition as defined above.
  • This process according to the invention makes it possible in particular to care for or make up said keratin materials, in particular the lips, the hair, the face and/or the eyelashes, by applying a composition, in particular lipstick, foundation, or mascara for the eyelashes or hair according to the invention.
  • a composition according to the invention may be in the form of a makeup composition for the skin and/or the lips, in particular for the skin of the face or of the body; it may be a product for the complexion, such as a foundation, a face powder or an eye shadow; a lip product, such as a lipstick or a lipcare product; a concealer product; a blusher, an eyeliner; a lip or eye pencil; a body makeup product; a gloss (lip gloss).
  • the composition according to the invention is dedicated to making up the skin and it is then more particularly a foundation, a face powder or an eye shadow, or a body makeup product.
  • the composition according to the invention is dedicated to making up the lips, and it is then more particularly a lipstick (in stick form) or a lip gloss (liquid lipstick).
  • the invention relates to a process for making up and/or caring for the skin and/or the lips, comprising at least the application, to said skin and/or said lips, of the composition as defined above.
  • ureidopyrimidone diisocyanate 70 g of ureidopyrimidone diisocyanate are dissolved in methyltetrahydrofuran, under argon. 80.3 g of octyldodecanol in 100 ml of dichloromethane are added, under argon, followed by 15 microlitres of dibutyltin dilaurate (catalyst). The reaction mixture is refluxed until disappearance of the isocyanate peak (2250-2265 cm "1 ) in IR spectrometry.
  • This powder can 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 isodo- decane, which then results in a solution that is viscous but can still be handled. It is therefore noted that, functionalization with a ureidopyrimidone brings about a change from a liquid oil to a solid, which can be carried in isododecane at concentrations above 30%.
  • Jarcol I-20 octyldodecanol
  • IPDI isophorone diiso- cyanate, 1 .1 eq.
  • the temperature of the reaction medium is then increased to 140°C and stirring is maintained for 1 hour at 140°C.
  • the reaction is monitored by infrared spectroscopy, with monitoring of the decrease in the peak characteristic of the isocyanate function.
  • the temperature is reduced to 70°C and then 30 ml of ethanol are added and the resulting mixture is stirred for one hour.
  • the medium is filtered through filter paper, the ethyl acetate is evaporated off and cyclohexane is added, and then washing is carried out 5 times with a mixture of NaCI-saturated water/ethanol (2V/1V).
  • the organic phase is then dried over Na 2 SO 4 , filtered, and stripped with isododecane.
  • the solvent is evaporated off and the resulting product is dried under reduced pressure, at 35°C overnight.
  • the desired product carried in isododecane at 50% of dry extract, is finally ob- tained.
  • the product is in particular characterized by HPLC and GPC (structure confirmed).
  • the disappearance of the peak is observed at 2250cm "1 .
  • the disappearance of the amine originating from the isocyto- sine is monitored by quantitative determination of amines.
  • the temperature is brought to 50°C, 100 ml of ethanol are added and stirring is maintained for 5 h.
  • the desired product carried in isododecane at 50% of dry extract, is obtained.
  • the product is in particular characterized by GPC and HPLC coupled to a mass spectrum.
  • the conversion of the isocyanate functions to urethane functions is monitored by IR spectroscopy, with disappearance of the band characteristic of the isocyanates at 2250 cm "1 .
  • the temperature is reduced to 50°C, and 100 ml of THF are added, followed by filtration through celite.
  • the THF fraction is precipitated from pentane, followed by separation of the organic phase by settling out.
  • the precipitate is then redissolved in THF and again precipitated from a methanol/water (1/1 ) mixture.
  • the desired product is obtained after filtration and drying under vacuum.
  • the solvent is evaporated off and the resulting product is dried under reduced pressure, at 35°C overnight.
  • dihydroxylated hydrogenated 1 ,2-polybutadiene polymer (GI3000 from the company Nisso) are dried at 80°C, under reduced pressure, overnight. This polymer is dissolved in 400 ml of anhydrous toluene. 25 ⁇ of catalyst (dibutyltin dilaurate) are added and the mixture is heated at 80°C, with stirring, until a homogeneous solution is obtained. 15 g of isocyanate-functionalized molecule having the following structure:
  • dihydroxylated hydrogenated 1 ,2-polybutadiene polymer (GI3000 from Nisso) are heated in the presence of 22 mg of catalyst (dibutyltin dilaurate) at 80°C, under reduced pressure, for 2 hours.
  • the temperature of the mixture is brought down to 20°C, under argon, followed by the addition of 60 ml of isododecane and 1 1 .6 g of 4,4'-dicyclohexylmethane diisocyanate.
  • the mixture is stirred for 16 hours at 20°C, under a controlled atmosphere, and is then heated to 120°C, followed by the addition of 40 ml of propylene carbonate.
  • the disappearance of the isocyanate functions is monitored by infrared spectroscopy, and then the tempera- ture of the medium is reduced to 70°C, followed by the addition of 30 ml of ethanol and stirring for 1 h. After the addition of ethyl acetate, the medium is filtered through filter paper. After evaporation of the ethyl acetate, cyclohexane is added, followed by 5 washes with a mixture of NaCI-saturated water/ethanol (2V/1 V). The organic phase is then dried over Na2SO 4 , filtered, and stripped with isododecane. A solution at 50% of dry extract of ureidopyrimidone-functionalized oil is then obtained.
  • Example 19 A/ Gloss measured using a glossmeter on a dry deposit of polymer
  • the coat covers at least the black background of the card.
  • the deposit is left to dry for 24 hours at a temperature of 23°C, and then the gloss at 20° is then measured on the black background using a Byk Gardner Micro-Tri-Gloss glossmeter.
  • a measurement at 20° higher than 50 is equivalent to a gloss considered to be acceptable, and if the measurement is greater than 60, the gloss is considered to be very satisfactory.
  • the coat covers at least the black background of the card.
  • the deposit is left to dry for 24 hours at a temperature of 23°C.
  • the wear resistance of the film formed is evaluated using a tribometer of pin-on-disc type; the substrate+film sample is moved and is in contact with a rubbing device which is a steel ball between 5 and 10 mm in diameter.
  • the load is between 0.25 and 3 N, and the movement speed is between 10 and 50 mm/s.
  • the number of passes of the rubbing device, in the same place, necessary in order to completely wear the film is measured. The higher this number, the greater the wear resistance of the film.
  • Formulations 1 to 4 illustrate the invention and formulation 5 is a comparative composition outside the invention.
  • FormulaFormulaFormulaFormulaFormulation 1 intion 2 (intion 3 (intion 4 (intion 5 vention) vention) vention) (outside the invention)
  • the pigments were milled in a part of the silicone oil by carrying out 3 passes of the mixture on the triple-roll mill.
  • the supramolecular polymer and/or the function- alized oils according to the invention were mixed with the rest of the silicone oil and the pigment mill base in a beaker or heating vessel. The mixture was then stirred with a Rayneri stirrer until it was homogeneous.
  • the formulations were poured into small pots which are leaktight with regard to the isododecane.
  • the staying power, and in particular the oil resistance, of the deposits produced with compositions 1 to 5 was evaluated visually, along with the residual gloss of the makeup deposits after having carried out the oil-resistance evaluation test.
  • a sample of each of the compositions was spread, at ambient temperature (25°C) over the surface of a polystyrene sheet. After drying of the deposits for 24 h at ambient temperature, olive oil was applied to the entire surface of the polystyrene sheet, so as to completely cover each of the deposits produced with the composi- tions to be evaluated.
  • a finger was applied to the deposit thus covered and a rotation was then performed while maintaining a constant pressure for a period of 30 seconds.
  • the surface was then wiped 3 times with a paper handkerchief.
  • Appearance Deposit of Deposit of Deposit of Deposit of Deposit very of the deuniform uniform uniform uniform uneven, posit thickness thickness thickness thickness fragmented and colour and colour and colour and colour (having dis ⁇
  • compositions in accordance with the invention make it possible to obtain a makeup deposit which exhibits good colour fastness, especially with respect to grease and in particular to oils, and good gloss fastness after drying at ambient temperature, in particular with regard to the deposit produced with comparative composition 5.
  • phase A2 The constituents of phase A2 were weighed out. The mixture was passed through a triple-roll mill. The constituents of phase A1 were weighed out into the main beaker and placed in a Rayneri stirrer. Phase A2 was then added. After stirring for 10 minutes, phase B was incorporated.
  • the formulations 1 , 2, 3 and 4 according to the invention exhibit a significantly improved application to the skin compared with the control composition 5. This is be- cause their texture is more fluid; they spread better on the skin.
  • the result obtained in the end is also more cosmetic and less tacky.
  • formulations can be classified according to their performance levels in meeting the following criteria (facilitated application and reduced tack):
  • Formulation 5 ⁇ formulation 1 ⁇ formulation 2 ⁇ formulation 3 ⁇ formulation 4.

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Abstract

La présente invention concerne une composition cosmétique qui comprend : a) a une huile supramoléculaire (composé A) qui peut être obtenue en faisant réagir une huile comportant au moins une fonction de réaction nucléophile et un groupe de liaison susceptible d'établir des liaisons hydrogènes ‑ ledit groupe de liaison comprenant une fonction de réaction susceptible de réagir avec la fonction de réaction de l'huile, et ledit groupe de liaison comprenant en outre au moins une unité de formule (Ia) ou (Ib): ‑, et b) un polymère supramoléculaire à base de polyalkène (composé B) qui peut être obtenu par la réaction d'un polymère polyalkène fonctionnalisé et d'un groupe de liaison fonctionnalisé, ledit groupe de liaison étant susceptible de former au moins trois liaisons H (hydrogènes). Par ailleurs, l'invention a trait à un processus de traitement cosmétique utilisant ladite composition.
PCT/EP2011/057783 2010-05-26 2011-05-13 Composition cosmétique comprenant une huile et un polymère, qui comportent chacun un groupe de liaison générant une liaison hydrogène, et procédé de traitement cosmétique WO2011147696A1 (fr)

Priority Applications (3)

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CN201180036081.5A CN103391765B (zh) 2010-05-26 2011-05-13 包含均携带产生氢键的接合基团的油和聚合物的美容组合物以及美容处理方法
EP11719274.0A EP2575751A1 (fr) 2010-05-26 2011-05-13 Composition cosmétique comprenant une huile et un polymère, qui comportent chacun un groupe de liaison générant une liaison hydrogène, et procédé de traitement cosmétique
US13/700,021 US20130136705A1 (en) 2010-06-09 2011-05-13 Cosmetic composition comprising an oil and a polymer both bearing a hydrogen-bond-generating joining group, and cosmetic treatment process

Applications Claiming Priority (4)

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FR1002226 2010-05-26
FR1002226A FR2960427B1 (fr) 2010-05-26 2010-05-26 Composition cosmetique comprenant une huile et un polymere portant tous deux un groupe de jonction generateur de liaisons hydrogene, et procede de traitement cosmetique
US35291110P 2010-06-09 2010-06-09
US61/352,911 2010-06-09

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FR2976805A1 (fr) * 2011-06-23 2012-12-28 Oreal Composition cosmetique comprenant un compose supramoleculaire capable d'etablir des liaisons hydrogene, et deux huiles siliconees particulieres distinctes
WO2013190705A1 (fr) * 2012-06-21 2013-12-27 L'oreal Composition cosmétique comprenant un polymère supramoléculaire, une huile de silicone non volatile et une huile d'hydrocarbure non volatile
US8709388B2 (en) 2012-03-12 2014-04-29 L'oreal Cosmetic composition based on a supramolecular polymer and a hyperbranched functional polymer
US20140154196A1 (en) * 2012-11-30 2014-06-05 L'oreal Cosmetic composition based on a supramolecular polymer and a silicone compound
US8846015B2 (en) 2012-03-12 2014-09-30 L'oreal Cosmetic compositions based on a supramolecular polymer, a hyperbranched functional polymer, a light silicone fluid and a copolymer of a silicone resin and a fluid silicone
WO2014197427A2 (fr) 2013-06-03 2014-12-11 R. J. Reynolds Tobacco Company Compositions cosmétiques comprenant un composant dérivé de graines de tabac
US9000051B2 (en) 2010-05-26 2015-04-07 L'oreal Cosmetic composition based on a supramolecular polymer and an absorbent filler
US9089502B2 (en) 2012-03-12 2015-07-28 L'oreal Cosmetic compositions based on a supramolecular polymer, a hyperbranched functional polymer, a light silicone fluid, a copolymer of a silicone resin and a fluid silicone, and a functional filler
US9730882B2 (en) 2012-03-12 2017-08-15 L'oreal Cosmetic composition based on a supramolecular polymer, a hyperbranched functional polymer and a polyethylene wax
EP2521533B1 (fr) * 2010-01-04 2018-05-02 L'Oréal Composition cosmétique, composé et procédé de traitement cosmétique
US10335361B2 (en) 2010-05-26 2019-07-02 L'oreal Cosmetic process for making-up and/or caring for the skin and/or the lips

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FR3059329A1 (fr) * 2016-11-30 2018-06-01 L'oreal Dispersion aqueuse de polymere supramoleculaire polyalcene et son utilisation en cosmetique
CN115429731B (zh) * 2022-10-09 2023-09-12 阿基米德(广州)化妆品研究有限公司 一种含超分子聚合物的美白祛斑组合物及其制备方法和应用

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EP2521533B1 (fr) * 2010-01-04 2018-05-02 L'Oréal Composition cosmétique, composé et procédé de traitement cosmétique
US10335361B2 (en) 2010-05-26 2019-07-02 L'oreal Cosmetic process for making-up and/or caring for the skin and/or the lips
US9000051B2 (en) 2010-05-26 2015-04-07 L'oreal Cosmetic composition based on a supramolecular polymer and an absorbent filler
WO2012175402A3 (fr) * 2011-06-23 2013-05-02 L'oreal Composition cosmetique comprenant un composé supramoléculaire pouvant établir des liaisons hydrogène et deux huiles de silicone particulières distinctes
US10653600B2 (en) 2011-06-23 2020-05-19 L'oreal Cosmetic composition comprising a supramolecular compound capable of establishing hydrogen bonds, and two particular distinct silicone oils
FR2976805A1 (fr) * 2011-06-23 2012-12-28 Oreal Composition cosmetique comprenant un compose supramoleculaire capable d'etablir des liaisons hydrogene, et deux huiles siliconees particulieres distinctes
US9730882B2 (en) 2012-03-12 2017-08-15 L'oreal Cosmetic composition based on a supramolecular polymer, a hyperbranched functional polymer and a polyethylene wax
US8709388B2 (en) 2012-03-12 2014-04-29 L'oreal Cosmetic composition based on a supramolecular polymer and a hyperbranched functional polymer
US8846015B2 (en) 2012-03-12 2014-09-30 L'oreal Cosmetic compositions based on a supramolecular polymer, a hyperbranched functional polymer, a light silicone fluid and a copolymer of a silicone resin and a fluid silicone
US9089502B2 (en) 2012-03-12 2015-07-28 L'oreal Cosmetic compositions based on a supramolecular polymer, a hyperbranched functional polymer, a light silicone fluid, a copolymer of a silicone resin and a fluid silicone, and a functional filler
JP2015523959A (ja) * 2012-06-21 2015-08-20 ロレアル 超分子ポリマー、不揮発性シリコーン油及び不揮発性炭化水素化油を含む化粧用組成物
WO2013190705A1 (fr) * 2012-06-21 2013-12-27 L'oreal Composition cosmétique comprenant un polymère supramoléculaire, une huile de silicone non volatile et une huile d'hydrocarbure non volatile
US20140154196A1 (en) * 2012-11-30 2014-06-05 L'oreal Cosmetic composition based on a supramolecular polymer and a silicone compound
WO2014197427A2 (fr) 2013-06-03 2014-12-11 R. J. Reynolds Tobacco Company Compositions cosmétiques comprenant un composant dérivé de graines de tabac
US10639269B2 (en) 2013-06-03 2020-05-05 R.J. Reynolds Tobacco Company Cosmetic compositions comprising tobacco seed-derived component

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FR2960427A1 (fr) 2011-12-02
EP2575751A1 (fr) 2013-04-10
CN103391765B (zh) 2016-08-24
FR2960427B1 (fr) 2015-03-27
CN103391765A (zh) 2013-11-13

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