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WO2011029738A1 - Composition comprenant un polymère basé sur des polyols particuliers, et méthode de traitement cosmétique - Google Patents

Composition comprenant un polymère basé sur des polyols particuliers, et méthode de traitement cosmétique Download PDF

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Publication number
WO2011029738A1
WO2011029738A1 PCT/EP2010/062624 EP2010062624W WO2011029738A1 WO 2011029738 A1 WO2011029738 A1 WO 2011029738A1 EP 2010062624 W EP2010062624 W EP 2010062624W WO 2011029738 A1 WO2011029738 A1 WO 2011029738A1
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formula
carbon atoms
linear
group
diisocyanate
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Céline Farcet
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LOreal SA
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LOreal SA
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/30—Low-molecular-weight compounds
    • C08G18/36—Hydroxylated esters of higher fatty acids
    • 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
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/34—Alcohols
    • A61K8/345—Alcohols containing more than one hydroxy group
    • 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
    • A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A61K8/88—Polyamides
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • 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
    • A61Q1/04—Preparations containing skin colorants, e.g. pigments for lips
    • A61Q1/06—Lipsticks
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/73—Polyisocyanates or polyisothiocyanates acyclic
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
    • C08G18/75—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic
    • C08G18/751—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring
    • C08G18/752—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group
    • C08G18/753—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate group
    • C08G18/755—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate group and at least one isocyanate or isothiocyanate group linked to a secondary carbon atom of the cycloaliphatic ring, e.g. isophorone diisocyanate
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
    • C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
    • C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
    • C11C3/003—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fatty acids with alcohols

Definitions

  • composition comprising a polymer based on particular polyols, and cosmetic treatment process
  • the present invention relates to the use of novel polymers in compositions intended to be used in the fields of cosmetics, dermatology, dermocosmetics, oral cosmetics and nutraceuticals, and also to the compositions thus obtained.
  • compositions for which gloss properties of the deposited film, after application to keratin materials, are desired. Examples that may be mentioned include lipsticks or nail varnishes.
  • gloss oils such as polybutenes, or fatty acid or alcohol esters with a high carbon number; or alternatively certain plant oils; or alternatively esters resulting from the partial or total esterification of a hydroxylated aliphatic compound with an aromatic acid, as described in patent application EP 1 097 699.
  • oils of triglyceride type in the present instance castor oil, functionalized with isophorone diisocyanate (IPDI), as described in US 5 707 612.
  • IPDI isophorone diisocyanate
  • the aim of the present invention is to propose compositions, especially cosmetic compositions, that can produce a uniform deposit on the substrate, the said de- posit combining gloss and staying power of the gloss, while at the same time being non-tacky and particularly comfortable to wear.
  • composition comprising, in a physiologically acceptable medium, a polymer that may be obtained by polymerization:
  • R'i represents H or a linear or branched alkyl group, comprising from 2 to 19 carbon atoms, the said alkyl group optionally being substituted with one or more groups OR a , R a representing H or a linear or branched alkyl group R', comprising from 1 to 18 carbon atoms;
  • - Ai represents a linear or branched divalent alkylene radical comprising from 2 to 18 carbon atoms
  • - R" represents (i) a linear or branched alkyl group R', comprising from 1 to 18 carbon atoms, or (ii) a group of formula -A 2 -OH,
  • a 2 representing a linear or branched divalent alkylene radical, comprising from 1 to 10 carbon atoms, optionally also substituted with one or more substituents chosen from the group formed from the phenylene radical and the radical of formula -(CH 2 OCH 2 )n-, n representing an integer between 1 and 100, preferably from 6 to 50 and preferentially equal to 6, 13 or 45;
  • a 2 preferably representing a radical of formula -CH 2 -A 3 -CH 2 -,
  • a 3 representing a phenylene radical or a group of formula -(CH 2 OCH 2 ) n -, n representing an integer between 1 and 100 and preferably equal to 6, 13 or 45;
  • R3 represents (i) a linear or branched alkyl group R 2 , comprising from 1 to 18 carbon atoms, or (ii) a group of formula -A 2 -O-Y', A 2 being as defined above and Y' representing a hydrogen atom or a group of formula ( ⁇ '):
  • R 3 represents a group of formula -A 2 -O-Y'
  • R 3 represents a group R 2 ;
  • X' represents, independently of each other, O or NH
  • D' represents either a linear, branched or cyclic, saturated or unsaturated divalent hydrocarbon-based block, comprising 2 to 42 carbon atoms; or a polymer block with an Mw of between 300 and 50 000 g/mol
  • - (iv) optionally at least one monofunctional derivative ⁇ 1 - ⁇ in which B1 is chosen from linear, branched or cyclic, saturated or unsaturated hydrocarbon-based radicals, comprising 1 to 80 carbon atoms; polymer blocks with an Mw of between 300 and 50 000 g/mol; and residues of natural or synthetic oils
  • X" represents O or NH
  • the physiologically acceptable medium comprises at least one ingredient chosen from volatile or non-volatile carbon-based, hydrocarbon-based, fluoro and/or silicone oils and/or solvents of mineral, animal, plant or synthetic origin; waxe
  • the invention thus allows the production of compositions, especially cosmetic compositions, formulated with polymers synthesized from plant oils.
  • polymerizing natural oils will make it possible to increase their viscosity and cohesion, thus making them capable of especially providing gloss and comfort. Furthermore, polymerizing them in the form of polyurethanes will make it possible to generate H bonds, which will facilitate the adhesion of the composition to keratin materials, and which will thus be favourable to better staying power of the oils.
  • the polymers according to the invention may be film-forming or non-film-forming. They may be polyurethanes or polyurethane-polyureas.
  • the polymers used in the context of the invention are soluble or dispersible in cosmetic formulation oils and lead, after application, to deposits that do not migrate within the fine lines and wrinkles of the skin or the lips; which are resistant to water, sweat, saliva and tears; and which generally afford prolonged staying power of the makeup.
  • R represents a divalent hydrocarbon-based radical, chosen from linear or branched aliphatic alkylene, cycloalkylene or aromatic radicals, and also mixtures thereof; comprising 1 to 20 carbon atoms, especially 8 to 18 or even 10 to 16 carbon atoms.
  • HMDI 1 ,6-hexamethylene diisocyanate
  • IPDI iso- phorone diisocyanate
  • MDI 4,4'-dicyclohexylnnethane diisocyanate
  • 1 ,5-naphthalene diisocyanate 4,4'-diphenylmethane diisocyanate
  • MDI 2,4-toluene diisocyanate
  • 2,6-toluene diisocyanate para-phenylene diisocyanate
  • cyclohexyl diisocyanate 2,2,4-thmethyl-1 ,6-hexamethylene diisocyanate
  • 3,3'-toluidene 4,4'-diisocyanate and 3,3'-dimethyl-4,4'-diphenylnnethane diisocyanate and mixtures thereof.
  • polyols that may be used in the context of the present invention correspond to the general formula (I") below:
  • R'i represents H or a linear or branched alkyl group, comprising from 2 to 19 carbon atoms, the said alkyl group possibly being substituted with one or more groups OR a , R a representing H or an alkyl group R' as defined below,
  • - Ai represents a linear or branched divalent alkylene radical, comprising from 2 to 18 carbon atoms
  • - R" represents (i) a linear or branched alkyl group R', comprising from 1 to 18 carbon atoms, or (ii) a group of formula -A 2 -OH,
  • a 2 representing a linear or branched divalent alkylene radical, comprising from 1 to 10 carbon atoms, option- ally also substituted with one or more substituents chosen from the group formed from the phenylene radical and the radical of formula -(CH 2 OCH 2 )n-, n representing an integer between 1 and 100, preferably from 6 to 50 and preferentially equal to 6, 13 or 45;
  • a 2 preferably representing a radical of formula -CH 2 -A 3 -CH 2 -,
  • a 3 representing a phenylene radical or a group of formula -(CH 2 OCH 2 ) n -, n represent- ing an integer between 1 and 100 and preferably equal to 6, 13 or 45;
  • R3 represents (i) a linear or branched alkyl group R 2 , comprising from 1 to 18 and preferably from 1 to 6 carbon atoms, or (ii) a group of formula -A 2 -O-Y', A 2 being as defined above and Y' representing a hydrogen atom or a group of formula ( ⁇ '):
  • R 3 represents a group of formula -A 2 -O-Y'
  • R 3 represents a group R 2 .
  • the polyols of formula (I") may be prepared via a process comprising the following steps: a) a step of epoxidation of a compound of formula (IV") below:
  • R"i representing H or a linear or branched alkyl group, comprising from 2 to 19 carbon atoms, the said alkyl group optionally containing one or two double bonds, and the said alkyl group also possibly being substituted, where appropriate, with an OH group,
  • R 4 representing an alkyl group F3 ⁇ 4 as defined above, or a group of for- mula -A 2 -O-Y'i, A 2 being as defined above and ⁇ representing a hydrogen atom or a group of formula ( ⁇ ):
  • R"'i representing H or a linear or branched alkyl group, comprising from 2 to 19 carbon atoms, the said alkyl group optionally containing one or two epoxide groups, and the said alkyl group also possibly being substituted, where appropriate, with an OH group,
  • R 5 representing an alkyl group R 2 as defined above, or a group of formula -A 2 -O-Y 2 , A 2 being as defined above and Y' 2 representing a hydrogen atom or a group of formula (A' 2 ):
  • Compound (IV"-1 ) may be obtained by transesterification of a plant oil, especially sunflower oil, rapeseed oil or castor oil, with an alcohol R 2 OH.
  • Compound (IV) may be obtained by transesterification of compound (IV"-1 ) with a diol HO-A 2 -OH.
  • a compound ( ⁇ -1 ) is then obtained, which is a compound of monoester type comprising at least two hydroxyl functions. It may optionally contain other hydroxyl functions as a function of the nature of RV
  • a compound ( ⁇ ) is then obtained, which is a compound of monoester or diester type (as a function of the nature of Y') comprising at least two hydroxyl functions. It may optionally contain other hydroxyl functions as a function of the nature of RV
  • the polyol compounds of formulae ( ⁇ -1 ) and ( ⁇ ) are particular, or even preferred, embodiments of the polyol compounds of formula (I").
  • the starting material (IV") contains a group R"i that may optionally contain one or two double bonds.
  • R"i may optionally contain one or two double bonds.
  • these double bonds may also be epoxidized, which accounts for the nature of the group R"'i.
  • the epoxide groups present in the group R"'i are then also modified, which accounts for the abovementioned definition of R'i and thus the possible presence of one or two hydroxyl groups in RV
  • the polyols are of formula ( ⁇ -1 ):
  • R'i represents H or a linear or branched alkyl group, comprising from 2 to 19 carbon atoms, the said alkyl group optionally being substituted with one or more groups OR a , R a representing H or a group R' as defined below,
  • - Ai represents a linear or branched divalent alkylene radical, comprising from 2 to 18 carbon atoms
  • a 2 representing a linear or branched divalent alkylene radical comprising from 1 to 10 carbon atoms, also optionally substituted with one or more substituents chosen from the group formed from the phenylene radical and the radical of formula -(CH 2 OCH 2 )n-, n representing an integer from 1 to 100, preferably from 6 to 50 and preferentially equal to 6, 13 or 45;
  • a 2 preferably representing a radical of formula -CH 2 -A 3 -CH 2 -, A 3 representing a phenylene radical or a group of formula - (CH 2 OCH 2 ) n -, n representing an integer between 1 and 100 and preferably equal to 6, 13 or 45;
  • R 2 represents a linear or branched alkyl group, comprising from 1 to 18 and pref- erably from 1 to 6 carbon atoms,
  • R"i representing H or a linear or branched alkyl group, comprising from 2 to 19 carbon atoms, the said alkyl group optionally containing one or two double bonds, and the said alkyl group also possibly being substituted, where appropriate, with an OH group,
  • R"'i representing H or a linear or branched alkyl group, comprising from 2 to 19 carbon atoms, the said alkyl group optionally containing one or two epoxide groups, and the said alkyl group also possibly being substituted, where appropriate, with an OH group, and b) a step of opening the epoxide ring with a diol of formula HO-A 2 -OH, A 2 being as defined above, to obtain a compound of formula ( ⁇ -1 ), and optionally c) a step of recovering the compound of formula ( ⁇ -1 ).
  • R'i represents H or a linear or branched alkyl group, comprising from 2 to 19 carbon atoms, the said alkyl group optionally being substituted with one or more groups OR a , R a representing H or a group R' as defined below,
  • R' represents a linear or branched alkyl group, comprising from 1 to 18 carbon atoms
  • - Ai represents a linear or branched divalent alkylene radical, comprising from 2 to 18 carbon atoms
  • a 2 represents a linear or branched divalent alkylene radical, comprising from 1 to 10 carbon atoms, also optionally substituted with one or more substituents chosen from the group formed from the phenylene radical and the radical of formula -(CH 2 OCH 2 )n-, n representing an integer from 1 to 100 and preferably from 6 to 50 and preferentially equal to 6, 13 or 45;
  • a 2 preferably representing a radical of formula -CH 2 -A 3 -CH 2 -, A 3 representing a phenylene radical or a group of formula - (CH 2 OCH 2 ) n -, n representing an integer from 1 to 100, preferably equal to 6, 13 or 45;
  • - Y' represents a hydrogen atom or a group of formula ( ⁇ '):
  • R' and R'i being as defined above in formula ( ⁇ ), and may be prepared by means of a preparation process comprising the following steps:
  • R"i representing H or a linear or branched alkyl group, comprising from 2 to 19 carbon atoms, the said alkyl group optionally containing one or two double bonds, and the said alkyl group also possibly being substituted, where appropriate, with an OH group,
  • R 2 representing a linear or branched alkyl group, comprising from 1 to 10, and preferably from 1 to 6, carbon atoms,
  • R"'i representing H or a linear or branched alkyl group, comprising from 2 to 19 carbon atoms, the said alkyl group optionally containing one or two epoxide groups, and the said alkyl group also possibly being substituted, where appropriate, with an OH group,
  • Y' 2 representing a hydrogen atom or a group of formula (A' 2 ):
  • the polyols used in the context of the invention may be obtained from fatty acid monoesters. These are generally obtained, for example, by transesterification of triglycerides with a short alcohol (R2OH, R 2 being as defined above), preferably with methanol or ethanol. These esters, and more particularly the methyl or ethyl esters of sunflower oil or castor oil, have thus been used as base 'synthons' in the preparation of the polyols used in the present invention.
  • the polyols according to the invention may be obtained via several synthetic routes, especially:
  • monoesters comprising in particular the transesterification of methyl esters of a plant oil to form monoesters, epoxidation and then ring opening;
  • diesters comprising in particular the transesterification of methyl esters of a plant oil to form diesters, epoxidation and ring opening.
  • the various reactions involved for the first two processes are (i) transesterification of the ester group with diols to graft a first primary hydroxyl function (abovemen- tioned step a)), (ii) epoxidation of the double bond (abovementioned step b)), fol- lowed by (iii) opening of the epoxide to give the second hydroxyl function (above- mentioned step c)).
  • R'i, R', Ai and A 2 are as defined above.
  • - R'i represents H or C2-C14 alkyl
  • - Ai represents a C2-C14 alkylene
  • - A 2 represents a C1 -C10 alkylene
  • R 2 represents a C1-C10 alkyl
  • R' represents a C1-C10 alkyl.
  • polyols according to the invention are diols. They may especially be of the
  • - Ri represents H or a linear or branched alkyl group, comprising from 2 to 19 even 2 to 14 carbon atoms,
  • the diols of formula (I) may be prepared via a process comprising the following steps:
  • the diols may also be of the general formula ( ⁇ -2) below:
  • - Ri represents H or a linear or branched alkyl group, comprising from 2 to 19 carbon atoms
  • the diols of formula ( -2) may be prepared via a process comprising the following step:
  • the diols of the invention of formulae (I) and ( -2) have the particular feature of being derived from natural fatty substances and of having an exact functionality of two.
  • the process of the invention for the preparation of compounds (I) and ( ) com- prises a first step of transesterification performed under heterogeneous catalysis (magnesium oxide or another heterogeneous catalyst) and preferably in the absence of solvent (clean synthesis).
  • heterogeneous catalysis magnesium oxide or another heterogeneous catalyst
  • the second step of the process of the invention for the preparation of compounds (I) and ( ⁇ ) is an epoxidation and this synthesis is particular on account of the presence of the terminal hydroxyl group of the monoesters.
  • the epoxidation requires the use of an already-formed peracid to avoid a side reaction with the alcohol at the end of the chain and the epoxide opening is possible only under relatively mild conditions to inhibit the formation of couplings.
  • the specificity of this second step consists in using preformed peracid.
  • the third step of the process of the invention for the preparation of compounds (I) and ( ⁇ ) consists in opening the epoxide with alcohols (methanol, ethanol, propanol, etc.) under acid catalysis.
  • the specificity of this step consists in that it preferably uses a recyclable and selective ion-exchange resin and is preferentially performed in the absence of solvent. It is also important to note that these three reactions follow each other without intermediate purification (a single purification may be performed at the end, which facilitates the implementation of the process).
  • Y is a hydrogen atom.
  • the diols thus obtained are non-symmetrical, and comprise a primary OH function (at the end of the chain) and a secondary OH function. They correspond to formula (1-1 ) below:
  • Y is a group of formula (A).
  • A is a group of formula (A).
  • Ai, A 2 and Ri being as defined above in formula (I).
  • the product of formula (V), obtained after step b), may also be in the form of a mixture of monoesters (V-1 ) and of diesters (V-2) of formulae:
  • - Ri represents H or a C2-C14 alkyl
  • R' represents a C2-C14 alkyl
  • - Ai represents a C2-C14 alkylene
  • - A 2 represents a C1 -C10 alkylene.
  • additional functional derivatives alone or as a mixture, corresponding to the formula HX'-D'-X'H, thus containing two active hydrogens that can each react with an isocyanate group, during the synthesis of the polymers accord- ing to the invention.
  • X' independently of each other, represents O or NH, and preferably X' denotes O.
  • D' denotes:
  • a polymer block with a Mw of between 300 and 50 000, or even between 400 and 10 000 and better still between 500 and 5000 g/mol .
  • D' When D' is a hydrocarbon-based block, it may originate from a natural or synthetic oil, or alternatively from the product of addition (dimer, trimer or polymer) of at least two unsaturated aliphatic chains, such as aliphatic radicals derived from dimeric fatty acids, for instance the products of addition between oleic chains, or of polyenes, preferably hydrogenated, such as hydrogenated polybutadiene or poly- isoprene, or polyolefins or copolyolefins.
  • D' When D' is a polymer block, it may origi- nate from ⁇ , ⁇ -difunctional polymers.
  • - diol polymers especially with an Mw of between 300 and 50 000, or even between 400 and 10 000, and better still between 500 and 5000 g/mol; or diol dimers; such as PTMO (polytetramethylene oxide), PEO (polyethylene oxide); polypropylene oxide (PPO), polyethylene adipate, polytetramethylene adipate, polycaprolactone or polydimethylsiloxanes containing OH end groups;
  • PTMO polytetramethylene oxide
  • PEO polyethylene oxide
  • PPO polypropylene oxide
  • polyethylene adipate polytetramethylene adipate
  • polycaprolactone polydimethylsiloxanes containing OH end groups
  • alkane diols especially of structure HO-D'-OH in which D' is a linear or branched alkyl chain, comprising from 2 to 40 carbon atoms and especially from 8 to 32 carbon atoms.
  • D' is a linear or branched alkyl chain
  • Mention may also be made of alkane diols of structure: HO-CH 2 -CH 2 OH-R2 in which R2 is an alkyl chain comprising 6 to 40 and especially 8 to 32 carbon atoms.
  • R2 is an alkyl chain comprising 6 to 40 and especially 8 to 32 carbon atoms.
  • Mention will be made, for example, of 1 ,12-dodecanediol, 1 ,10-decanediol, 1 ,4-butanediol, 1 ,6-hexanediol and ethylene glycol;
  • - amino alcohols especially linear or branched, comprising 2 to 32 carbon atoms and in particular 4 to 18 carbon atoms;
  • - polydienes containing hydroxyl end groups which are preferably hydrogenated; these are, for example, the derivatives defined in FR-2782723. They are preferably chosen from polybutadiene, polyisoprene and poly(1 ,3-pentadiene) ho- mopolymers and copolymers. These oligomers preferably have an Mn of less than 7000 and preferably between 1000 and 5000. They preferably have chain-end functionality of from 1 .8 to 3 and better still in the region of 2.
  • These polydienes containing hydroxyl end groups are, for example, the hydroxylated polybutadienes sold by the company Elf Atochem under the brand names Poly BD-45H® and Poly BD R-20 LM®. Mention may be made especially of 1 ,4-polybutadiene diol;
  • polyolefins containing hydroxyl end groups which may be homopolymers or copolymers containing ⁇ , ⁇ -hydroxyl end groups, for instance polyisobutylene and polyethylene-butylene containing ⁇ , ⁇ -hydroxyl end groups, or polymers having the structure below, such as those sold by the company Mitsubishi under the brand name Polytail®: or hydrogenated polybutadienes containing hydroxyl end functions, such as GI1000, GI2000 and GI3000 from Nisso PB.
  • these polymers have an Mw of between 300 and 50 000, or even between 400 and 10 000 and better still between 500 and 5000 g/mol;
  • polyesters with an alkyl chain bearing at least two reactive groups, which may be poly(12-hydroxystearate) containing hydroxyl end groups.
  • This polyester is obtained by self-condensation of 1 ,2-hydroxystearic acid, followed by reaction with a polyol to consume the residual acid groups.
  • these polymers have an Mw of between 300 and 50 000, or even between 400 and 10 000 and better still between 500 and 5000 g/mol;
  • R 1 is a linear or branched C8-C30 alkyl chain, for instance glyceryl monostearate.
  • diamine dimers and diamines containing an aliphatic chain especially of C2-C40, or even of C6-C32.
  • Their use allows the introduction into the polymer of urea groups instead of urethane groups.
  • diamine dimers having the same structure as the diol dimers or alkane diols described previously may be used, i.e. diamine dimers comprising two primary amine functions instead of hydroxyl groups. These diamine dimers may be obtained from the transformation of fatty acid dimers.
  • diamines of structure H 2 N-D'-NH 2 may be used, in which D' is a linear or branched alkyl chain, comprising 2 to 40 carbon atoms.
  • diamines may preferably be used as a mixture with a difunctional derivative chosen from diol dimers, alkane diols, polydi- enes and polyolefins containing hydroxyl end groups, branched polyesters with a long alkyl chain, and oils bearing 2 to 3 hydroxyl groups, as mentioned previously.
  • a difunctional derivative chosen from diol dimers, alkane diols, polydi- enes and polyolefins containing hydroxyl end groups, branched polyesters with a long alkyl chain, and oils bearing 2 to 3 hydroxyl groups, as mentioned previously.
  • diamines mention may be made of ethylenediamine, 1 ,10-diaminodecane, 1 ,12-diaminododecane, and also diamine oils such as coco- propylenediamine (distilled or undistilled), hydrogenated or non-hydrogenated tal- lowpropylenediamine, C16-C22 alkylpropylenediamine, oleylpropylenediamine and 4,4'-methylenebis(2-chloroaniline).
  • diamine oils such as coco- propylenediamine (distilled or undistilled), hydrogenated or non-hydrogenated tal- lowpropylenediamine, C16-C22 alkylpropylenediamine, oleylpropylenediamine and 4,4'-methylenebis(2-chloroaniline).
  • an additional difunctional derivative chosen from oils bearing three hydroxyl groups per chain for instance castor oil, which may or may not be hydrogenated, will be used.
  • Difunctional derivatives that may especially be mentioned include poly(ethylene oxide) or PEG, poly(propylene oxide), polytetramethylene oxide (PTMO), polyiso- butylene, 1 ,4-polybutadiene diol, polyethylene adipate, polytetramethylene adipate, polycaprolactone, polydimethylsiloxane di-OH, castor oil; 1 ,4-butanediol, 1 ,2- propanediol, 1 ,3-propanediol, 1 ,6-hexanediol, ethylene glycol; ethylenediamine and a mixture thereof.
  • PTMO polytetramethylene oxide
  • One or more monofunctional derivatives, of formula ⁇ 1 - ⁇ , containing only one active hydrogen that can react with an isocyanate group, to consume the residual isocyanate groups that have not entirely reacted with the difunctional reagents, may also be used in the preparation of the polymer according to the invention; two different difunctional derivatives may thus especially be used.
  • the monofunctional derivatives are advantageously chosen from monoalcohols or monoamines with linear or branched alkyl chains comprising from 1 to 80 carbon atoms; polymers bearing only one OH or NH 2 reactive function and having an Mw of between 300 and 50 000, or even between 400 and 10 000, and better still between 500 and 5000 g/mol; natural or synthetic oils bearing only one hydroxyl group per chain, for instance glycerol diesters or triesters of citric acid and of a fatty alcohol .
  • X" represents O or NH.
  • the radical B1 is preferably chosen from linear, branched or cyclic, saturated or unsaturated hydrocarbon-based radicals, comprising 1 to 80 carbon atoms and especially 2 to 40 carbon atoms; polymer blocks with an Mw of between 300 and 50 000 g/mol and residues of natural or synthetic oils.
  • the polymers according to the invention may be readily prepared by a person skilled in the art on the basis of his general knowledge.
  • the mole proportion between the main monomers of the polymerization reaction depends on the chemical structure and the molecular weight of the polymers (polyurethanes and polyurethane-polyureas) that it is desired to obtain, as is conventionally the case in polyurethane and polyurea chemistry.
  • the order of introduction of the monomers may be adapted to this chemistry.
  • the diisocyanates are preferably present in a molar amount of from 0.2 to 1 .5 parts of diisocyanate, especially 0.45 to 1 .15 parts of diisocyanate, better still 0.5 to 1 .05 parts of diisocyanate, or even 0.6 to 0.95 part of diisocyanate, per 1 part of total difunctional derivatives (compounds (ii) and (iii) if present).
  • the polymerization reaction is preferentially performed with a slight deficit of diisocyanate relative to the reaction stoichiometry, to avoid crosslinking of the polymer and to maintain good solubility.
  • the polyols of formula (I") represent 0.1 to 100 mol%, especially 50 to 99 mol%, or even 70 to 98 mol% and better still 80 to 95 mol%, relative to the total number of moles of difunctional compounds ((ii) and (iii) if present).
  • the monofunctional derivatives when they are present, represent about 0.5 to 50 mol% relative to the total number of moles of difunctional compounds ((ii) and (iii) if present). They are generally added at the end of the polym- erization reaction, in excess relative to the residual diisocyanates, so as to react with all the unreacted NCOs.
  • the polymerization is conventionally performed in the absence of solvent, or in an organic solvent that is capable of dissolving the monomers and optionally the formed polymer.
  • This solvent is preferably readily removable at the end of the reaction, especially by distillation, and does not react with the isocyanate groups.
  • each of the monomers is dissolved in part of the organic solvent before the polymerization reaction.
  • Solvents that may especially be mentioned include THF (tetrahydrofuran), DMF, DMSO and dichloromethane.
  • the reaction is pref- erably performed without solvent (bulk reaction).
  • a catalyst may also be used to activate the polymerization. This is generally chosen from the catalysts commonly used in polyurethane and polyurea chemistry, for instance tin 2-ethylhexanoate and dibutyltin laurate (DBTL).
  • DBTL dibutyltin laurate
  • the monomers, optionally the catalyst and optionally the solvent, may be added in batch mode (all simultaneously) or alternatively by semi-continuous addition.
  • the process is performed in batch mode.
  • the mixture may be heated, for example, to a temperature of between 40 and 150°C and preferably between 50 and 90°C, for a time that may be between 4 and 15 hours and especially 5 to 12 hours.
  • the polymers, polyurethanes and/or polyureas of the invention preferably have a weight-average molecular mass (Mw) of between 500 and 500 000 g/mol, espe- daily between 800 and 100 000 g/mol, better still between 1000 and 50 000 g/mol and preferentially between 1500 and 30 000 g/mol, as measured at the top of the steric exclusion chromatography peak.
  • Mw weight-average molecular mass
  • the polymers according to the invention find a particular application in the field of cosmetics, dermatology, dermocosmetics, oral cosmetics and nutraceuticals.
  • polymers according to the invention may be used alone or mixed together.
  • compositions according to the invention are cosmetic, dermatological, dermo- cosmetic, or even oral cosmetic or neutraceutical compositions, and comprise, besides the said polymers, a medium that is acceptable for the intended application, especially a cosmetically or dermatological ly acceptable medium, i.e. a me- dium that is compatible with keratin materials such as facial or bodily skin, the lips, the hair, the eyelashes, the eyebrows and the nails.
  • a cosmetically or dermatological ly acceptable medium i.e. a me- dium that is compatible with keratin materials such as facial or bodily skin, the lips, the hair, the eyelashes, the eyebrows and the nails.
  • the said composition may advantageously comprise a liquid fatty phase, which may advanta- geously constitute a solvent medium for the polymers according to the invention, and which may comprise at least one compound chosen from volatile or nonvolatile carbon-based, hydrocarbon-based, fluoro and/or silicone oils and/or solvents of mineral, animal, plant or synthetic origin, alone or as a mixture, provided that they form a stable, homogeneous mixture and are compatible with the in- tended use.
  • a liquid fatty phase which may advanta- geously constitute a solvent medium for the polymers according to the invention, and which may comprise at least one compound chosen from volatile or nonvolatile carbon-based, hydrocarbon-based, fluoro and/or silicone oils and/or solvents of mineral, animal, plant or synthetic origin, alone or as a mixture, provided that they form a stable, homogeneous mixture and are compatible with the in- tended use.
  • the term 'volatile' means any compound that is capable of evaporating on contact with keratin materials, or the lips, in less than one hour, at room temperature (25°C) and atmospheric pressure (1 atm).
  • This volatile compound especially has a non-zero vapour pressure, at room temperature and atmospheric pressure, especially ranging from 0.13 Pa to 40 000 Pa (10 "3 to 300 mmHg).
  • the term 'non-volatile' refers to a compound that remains on keratin materials or the lips at room temperature and atmospheric pressure for at least one hour and that especially 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 solvent that may be chosen, alone or as a mixture, from:
  • esters of monocarboxylic acids with monoalcohols and polyalcohols advantageously, the said ester is a C12-C15 alkyl benzoate or corresponds to the follow- ing 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 from 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 from 3 to 30 carbon atoms and better still from 3 to 20 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 heteroa- toms 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 or hydroxyl .
  • groups R'i are those derived from fatty acids, preferably higher fatty acids chosen from the group formed from 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, be- henic acid, oleic acid, linolenic acid, linoleic acid, oleostearic acid, arachidonic acid and erucic acid, and mixtures thereof.
  • R'i is an unsubstituted branched alkyl group of 4 to 14 carbon atoms and preferably from 8 to 10 carbon atoms and R2 is an unsubstituted branched alkyl group of 5 to 15 carbon atoms and preferably from 9 to 1 1 carbon atoms.
  • Mention may be made more particularly of linear, branched and/or cyclic C5-C48 alkanes, and preferentially branched C8-C16 alkanes, for instance C8-C16 isoal- kanes of petroleum or non-petroleum origin (also known as isoparaffins); especially decane, heptane, undecane, dodecane, tridecane, cyclohexane; and also isododecane, isodecane and isohexadecane; and mixtures thereof.
  • C8-C16 isoal- kanes of petroleum or non-petroleum origin also known as isoparaffins
  • decane, heptane, undecane, dodecane, tridecane, cyclohexane also isododecane, isodecane and isohexadecane; and mixtures thereof.
  • volatile silicone oils that may be mentioned include volatile linear or cyclic 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, dodecamethylcyclo- hexasiloxane, heptamethylhexyltrisiloxane, heptamethyloctyltrisiloxane, hexame- thyldisiloxane, octamethyltrisiloxane, decamethyltetrasiloxane, dodecamethylpen- tasiloxane and methylhexyldimethylsiloxane, and mixtures thereof.
  • volatile linear or cyclic silicone oils especially those with a viscosity of
  • 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, these groups each containing from 2 to 24 carbon atoms, phenyl silicones, for instance phenyl trimethicones, phenyl dimethicones, phenyltrimethylsiloxydiphenylsiloxanes, di- phenyl dimethicones, diphenylmethyldiphenyltrisiloxanes, and 2-phenylethyl trimethylsiloxysilicates.
  • PDMS polydimethylsiloxanes
  • polydimethylsiloxanes comprising alkyl or alkoxy groups, which are pendant and/or at the end of a silicone chain, these groups each containing from 2 to 24 carbon atoms
  • phenyl silicones for instance phenyl trime
  • the volatile oils especially carbon-based oils, alone or as a mixture, are present in the composition in an amount of between 30% and 80% by weight, especially 35% to 75% by weight or even 40% to 70% by weight relative to the total weight of the composition.
  • 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 such as perfluorodecalin, perfluoroadamantanes, perfluoroalkyl phosphate monoesters, diesters and triest- ers, and fluoro ester oils;
  • propylene glycol ethers that are liquid at room temperature (25°C) such as propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate and dipropylene glycol mono-n-butyl ether;
  • - C8-C32 fatty acids for instance oleic acid, linoleic acid and linolenic acid, and mixtures thereof;
  • - difunctional oils comprising two functions chosen from ester and/or amide and comprising from 6 to 30 carbon atoms, especially 8 to 28 carbon atoms and better still 10 to 24 carbon atoms, and 4 heteroatoms chosen from O and N; preferably, the amide and ester functions being in the chain;
  • ketones that are liquid at room temperature (25°C), especially C3-C10 ketones, such as methyl ethyl ketone, methyl isobutyl ketone, diisobutyl ketone, isophorone, cyclohexanone and acetone;
  • aldehydes that are liquid at room temperature (25°C) such as benzaldehyde and acetaldehyde.
  • the liquid fatty phase may represent 5% to 90% by weight of the composition, es- pecially from 10% to 75% by weight, in particular from 15% to 60% by weight, or even from 25% to 55% by weight relative to the total weight of the composition.
  • composition according to the invention may also comprise one or more physiologically acceptable organic solvents.
  • These solvents may generally be present in a content ranging from 0.1 % to 90%, preferably from 0.5% to 85%, more preferably from 10% to 80% by weight and better still from 30% to 50% relative to the total weight of the composition.
  • hydrophilic organic solvents such as alcohols and especially linear or branched lower monoalcohols containing from 2 to 5 carbon atoms, for instance ethanol, isopropanol or n-propanol; polyols, for instance glycerol, diglycerol, propylene glycol, sorbitol or pentylene glycol; polyethylene glycols, or alternatively C2 ethers and hydrophilic C2-C 4 aldehydes.
  • hydrophilic organic solvents such as alcohols and especially linear or branched lower monoalcohols containing from 2 to 5 carbon atoms, for instance ethanol, isopropanol or n-propanol
  • polyols for instance glycerol, diglycerol, propylene glycol, sorbitol or pentylene glycol
  • polyethylene glycols or alternatively C2 ethers and hydrophilic C2-C 4 aldehydes.
  • ketones that are liquid at room temperature (25°C), such as methyl ethyl ketone, methyl isobutyl ketone, diisobutyl ketone, isophorone, cyclohexanone and acetone; propylene glycol ethers that are liquid at room temperature (25°C), such as propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, dipropylene glycol mono-n-butyl ether; short-chain esters (containing from 3 to 8 carbon atoms in to- tal) such as ethyl acetate, methyl acetate, propyl acetate, n-butyl acetate or isopentyl acetate; ethers that are liquid at 25°C, such as diethyl ether, dimethyl ether or dichlorodiethyl ether; alkanes that are liquid at 25°C, such as decane, heptane, do
  • the composition may also comprise fatty substances that are solid at room temperature (25°C), such as waxes, pasty fatty substances and gums, and mixtures thereof. They may be of animal, plant, mineral or synthetic origin.
  • the term "wax” means a lipophilic compound, which is solid at room temperature (25°C), with a reversible solid/liquid change of state, with a melting point of greater than or equal to 25°C, which may be up to 120°C.
  • a melting point of the wax may be measured using a differential scanning calorimeter (D.S.C.), for example the calorimeter sold under the name DSC 30 by the company Mettler.
  • the waxes may be hydrocarbon-based, fluoro and/or silicone waxes and may be of plant, mineral, animal and/or synthetic origin. In particular, the waxes have a melting point of greater than 30°C and better still greater than 45°C.
  • waxes that may be used in the composition of the invention mention may be made of beeswax, carnauba wax or candelilla wax, paraffin, microcrystal- line waxes, ceresin or ozokerite; synthetic waxes such as polyethylene waxes or Fischer-Tropsch waxes, silicones waxes such as alkyl or alkoxy dimethicones containing from 16 to 45 carbon atoms.
  • the gums are generally polydimethylsiloxanes (PDMS) of high molecular weight or cellulose gums or polysaccharides and the pasty substances are generally hydro- carbon-based compounds, for instance lanolins and derivatives thereof, or alternatively PDMS.
  • PDMS polydimethylsiloxanes
  • pasty fatty substance means a viscous product containing a liquid fraction and a solid fraction. Mention may be made especially of fatty substances with a melting point ranging from 20 to 55°C and/or a viscosity at 40°C ranging from 0.1 to 40 Pa.s (1 to 400 poises) measured with a Contraves TV or Rheomat 80 viscometer.
  • a person skilled in the art can select the spindle for measuring the viscosity from the spindles MS-r3 and MS-r4 on the basis of his general knowledge, so as to be able to measure the viscosity of the pasty compound tested.
  • the melting point values correspond, according to the invention, to the melting peak meas- ured by the differential scanning calorimetry method with a temperature rise of 5 or 10°C/minute.
  • these fatty substances are hydrocarbon-based compounds (mainly containing carbon and hydrogen atoms and possibly ester groups), optionally of polymer type; they may also be chosen from silicone and/or fluoro compounds; they may also be in the form of a mixture of hydrocarbon-based and/or silicone and/or fluoro compounds.
  • the hydrocarbon-based pasty compounds are preferably used in predominant proportion.
  • lanolins and lanolin derivatives for instance acetyl lanolins or oxypropylene lanolins or isopro- pyl lanolate; fatty acid or fatty alcohol esters, especially those containing from 20 to 65 carbon atoms, for instance triisostearyl or cetyl citrate; arachidyl propionate; polyvinyl laurate; cholesterol esters such as triglycerides of plant origin, such as hydrogenated plant oils, viscous polyesters, for instance poly(12-hydroxystearic acid), and mixtures thereof.
  • lanolins and lanolin derivatives for instance acetyl lanolins or oxypropylene lanolins or isopro- pyl lanolate
  • fatty acid or fatty alcohol esters especially those containing from 20 to 65 carbon atoms, for instance triisostearyl or cetyl citrate
  • arachidyl propionate polyvinyl laurate
  • cholesterol esters such as
  • triglycerides of plant origin use may be made of hydrogenated castor oil derivatives. Mention may also be made of silicone pasty fatty substances such as polydimethylsiloxanes (PDMS) with side chains of the alkyl or alkoxy type containing from 8 to 24 carbon atoms, for instance stearyl di- methicones.
  • PDMS polydimethylsiloxanes
  • the composition may contain from 0.1 % to 50% by weight and better still from 1 % to 30% by weight of waxes relative to the total weight of the composition.
  • the composition may also comprise one or more hydrophilic organic solvents such as alcohols and especially linear or branched monoalcohols containing from 2 to 5 carbon atoms, for instance ethanol, isopropanol or n-propanol; polyols, for instance glycerol, diglycerol, propylene glycol, sorbitol or pentylene glycol; polyeth- ylene glycols, or alternatively C2 ethers and hydrophilic C2-C 4 aldehydes.
  • Solvents could be used alone or in mixture with water; water or a mixture of water and of hydrophilic organic solvents may be present in the composition according to the invention in a content of from 10% to 80% by weight relative to the total weight of the composition.
  • the composition may also be anhydrous.
  • composition according to the invention may also comprise one or more dye- stuffs chosen from pulverulent compounds, for instance pigments, fillers, nacres and glitter flakes, and/or liposoluble or water-soluble dyes.
  • dye- stuffs chosen from pulverulent compounds, for instance pigments, fillers, nacres and glitter flakes, and/or liposoluble or water-soluble dyes.
  • the dyestuffs especially pulverulent dyestuffs, may be present in the composition in a content of from 0.01 % to 50% by weight, preferably from 0.1 % to 40% by weight or even from 1 % to 30% by weight relative to the weight of the composition.
  • pigments should be understood as meaning 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.
  • nacres should be understood as meaning iridescent particles of any shape, especially produced by certain molluscs in their shell, or else synthesized.
  • the pigments may be white or coloured, mineral and/or organic, and interference or non-interference pigments.
  • mineral pigments that may be mentioned are titanium dioxide, optionally surface-treated, zirconium oxides or cerium oxides, and also iron oxides or chromium oxides, manganese violet, ultramarine blue, chromium hydrate and ferric blue.
  • organic pigments that may be mentioned are carbon black, pigments of D & C type and lakes based on cochineal carmine or on barium, strontium, calcium or aluminium.
  • the nacreous pigments may be chosen from white nacreous pigments such as mica coated with titanium or with bismuth oxychloride, coloured nacreous pigments such as titanium mica with iron oxides, titanium mica especially with ferric blue or with chromium oxide, titanium mica with an organic pigment of the above- mentioned type, and also nacreous pigments based on bismuth oxychloride.
  • the fillers may be mineral or organic, and lamellar or spherical. Mention may be made of talc, mica, silica, kaolin, Nylon powder and polyethylene powder, poly- ⁇ - alanine powder and polyethylene powder, Teflon, lauroyllysine, starch, boron nitride, powders of tetrafluoroethylene polymers, hollow microspheres such as Ex- pancel (Nobel Industrie), Polytrap (Dow Corning) and silicone resin microbeads (for example Tospearls from Toshiba), precipitated calcium carbonate, magnesium carbonate, magnesium hydrocarbonate, hydroxyapatite, hollow silica microspheres (Silica Beads from Maprecos), glass or ceramic microcapsules, and metal soaps derived from organic carboxylic acids containing from 8 to 22 carbon atoms and preferably from 12 to 18 carbon atoms, for example zinc, magnesium or lithium stearate, zinc laurate or magnesium myristate.
  • the liposoluble dyes are, for example, Sudan red, DC Red 17, DC Green 6, ⁇ -carotene, soybean oil, Sudan brown, DC Yellow 1 1 , DC Violet 2, DC Orange 5 and quinoline yellow. They may represent 0.01 % to 20% and better still from 0.1 % to 6% of the weight of the composition.
  • the water-soluble dyes are, for example, beetroot juice or methylene blue, and may represent 0.01 % to 6% of the total weight of the composition.
  • the composition according to the invention may also comprise one or more fillers, especially in a content ranging from 0.01 % to 50% by weight and preferably ranging from 0.02% to 30% by weight relative to the total weight of the composition.
  • fillers should be understood as meaning colourless or white, mineral or synthetic, lamellar or non-lamellar particles, which are intended to give body or rigidity to the composition, and/or softness, matting and uniformity to the makeup.
  • the fillers may be mineral or organic of any shape, platelet-shaped, spherical or oblong.
  • talc Mention may be made of talc, mica, silica, kaolin, polyamide powder (Nylon®), ⁇ - ⁇ -alanine powder and polyethylene powder, powders of tetrafluoroethylene polymers (Teflon®), lauroyllysine, starch, boron nitride, hollow polymer microspheres such as those of polyvinylidene chloride/acrylonitrile, for instance Expancel® (Nobel Industrie), or of acrylic acid copolymers (Polytrap® from the company Dow Corning) and silicone resin microbeads (for example Tospearls® from Toshiba), elastomeric polyorganosiloxane particles, precipitated calcium carbonate, magnesium carbonate, magnesium hydrocarbonate, hydroxyapatite, hoi- low silica microspheres (Silica Beads® from Maprecos), glass or ceramic microcapsules, and metal soaps derived from organic carboxylic acids containing from 8 to 22 carbon atom
  • the composition may also comprise an additional polymer such as a film-forming polymer.
  • film-forming polymer means a polymer that is capable of forming, by itself or in the presence of an auxiliary film-forming agent, a continuous film that adheres to a support, especially to keratin materials.
  • synthetic polymers of radical type or of polycondensate type, polymers of natural origin and mixtures thereof, in particular acrylic polymers, polyurethanes, polyesters, polyamides, polyureas, and cellulose-based polymers, for instance nitrocellulose.
  • composition according to the invention may also comprise ingredients commonly used in cosmetics, such as vitamins, thickeners, gelling agents, trace elements, softeners, sequestrants, fragrances, acidifying or basifying agents, preserving agents, sunscreens, surfactants, antioxidants, hair-loss counteractants, anti- dandruff agents, propellants, ceramides and auxiliary film-forming agents, or mixtures thereof.
  • ingredients commonly used in cosmetics such as vitamins, thickeners, gelling agents, trace elements, softeners, sequestrants, fragrances, acidifying or basifying agents, preserving agents, sunscreens, surfactants, antioxidants, hair-loss counteractants, anti- dandruff agents, propellants, ceramides and auxiliary film-forming agents, or mixtures thereof.
  • the composition according to the invention may be in the form of a suspension, a dispersion especially of oil in water by means of vesicles; an optionally thickened or even gelled aqueous or oily solution; an oil-in-water, water-in-oil or multiple emulsion; a gel or a mousse; an oily or emulsified gel; a dispersion of vesicles, especially lipid vesicles; a two-phase or multi-phase lotion; a spray; a loose, compact or cast powder; an anhydrous paste.
  • This composition may have the appearance of a lotion, a cream, a pomade, a soft paste, an ointment, a mousse, a cast or moulded solid, especially in stick or dish form, or a compacted solid.
  • the cosmetic composition according to the invention may be in the form of a product for caring for, cleansing or making up bodily or facial skin, the lips, the nails, the eyelashes, the eyebrows and/or the hair, an antisun or self-tanning product, a hair product for caring for, treating, shaping, making up or colouring the hair.
  • a makeup composition especially a complexion product such as a foundation, a face powder or an eyeshadow; a lip product such as a lipstick, a lip gloss or a lipcare product; a concealer product; a blusher, a mascara or an eyeliner; an eyebrow makeup product, a lip or eye pencil; a nail product such as a nail varnish or a nailcare product; a body makeup product; a hair makeup product (hair mascara or lacquer).
  • It may also be in the form of a protective or care product for the skin of the face, the neck, the hands or the body, especially an antiwrinkle composition, a moisturizing or treating composition; an antisun or artificial tanning (self-tanning) composi- tion.
  • haircare product especially for colouring, holding the hairstyle, shaping the hair, caring for, treating or cleansing the hair, such as shampoos, hair conditioners, hairsetting gels or lotions, blow-drying lotions, and fixing and styling compositions such as lacquers or sprays.
  • the cosmetic composition according to the invention is in the form of a makeup product, especially a liquid lip gloss or lipstick, a foundation, a care cream; or a hair product, especially for conditioning or caring for the hair or a hair conditioner.
  • a subject of the invention is also a cosmetic treatment process, especially for making up or caring for keratin materials such as bodily or facial skin, the lips, the nails, the hair, the eyebrows and/or the eyelashes, comprising the application to the said materials of a cosmetic composition as defined previously. This process especially allows the skin, the hair and/or the lips to be made up.
  • composition comprising:
  • Step 3 Preparation of epoxidized butanediol esters of oleic sunflower oil (3) of
  • the starting material is compound (2) as obtained in step 2 above, having the following composition: 83.7% by weight of diesters, 8.80% by weight of monoesters and 7.50% by weight of ethyl ester (compound (1 )).
  • the starting material is compound (3) as obtained in step 3 above, having the fol- lowing composition: 86.8% by weight of diesters, 7.3% by weight of monoesters and 5.9% by weight of ethyl ester (compound (1 )).
  • oleic sunflower oil (OSO)(ITERG) were placed in a jacketed reactor with 161 .5 g of absolute ethanol. The whole was mixed with stirring at 650 rpm and heated to 65°C. 5.5880 g of NaOMe were then added to the reactor, and a change in the colour of the product and the appearance of immediate cloudiness were then observed. The whole was then left to react for 5 hours at 70°C. The resulting reaction mixture was then transferred into a separating funnel so as to remove the glycerol and to evaporate off the ethanol. Neutralization was then performed with a few drops of HCI, followed by washing with water to neutrality. Finally, the residual water was distilled off on a rotavapor.
  • OSO oleic sunflower oil
  • ITERG absolute ethanol
  • Step 2 Preparation of epoxidized ethyl esters of sunflower oil (7) of formula:
  • a 2 may represent a radical chosen from the following radicals: C 3 H 6 , C 4 H 8 , C 5 Hi 0 , C 6 Hi 2 , H 2 C-(CH 2 OCH2)6-CH2, H2C-(CH2OCH2)i 3-CH2, H2C-(CH2OCH2) 4 5-CH2 or H2C-C6H 4 -CH2.
  • the diesters are derived from the transesterification of an oleic methyl ester and of a diol (propanediol, butanediol, pentanediol, hexanediol or polyethylene oxide (300 g/mol, 600 g/mol and 2000 g/mol)).
  • the synthesis involved 0.1 mol of oleic methyl ester and 0.05 mol of diol, in the presence of magnesium oxide MgO (catalyst, 1 % by mass relative to the mass of methyl ester).
  • MgO magnesium oxide
  • the medium was stirred at 160°C under a stream of nitrogen for 7 hours.
  • the methanol formed by the reaction was removed from the reaction medium by means of a Dean-Stark trap.
  • the formation of the diester was monitored by 1 H NMR. After 7 hours, the medium was placed at 200°C under a dynamic vacuum for 1 hour so as to remove the residual oleic methyl ester
  • epoxide-opening step 10 mmol of epoxidized diesters were dissolved in 100 mmol of ethanol, in the presence of ion-exchange resin (Amberlyst 15 Dry, 4% by mass relative to the mass of diesters).
  • the reaction medium was stirred at 75°C for 20 hours.
  • the epoxide opening was monitored by 1 H NMR.
  • the catalyst was removed by filtration.
  • the excess ethanol was then evaporated off under reduced pressure.
  • the hydroxylated diesters were then analysed by 1 H NMR and by steric exclusion chromatography. Their hydroxyl number was determined.
  • Example 5 Preparation of diols of formula (1-1 ) with a primary alcohol function and a secondary alcohol function
  • a 2 may represent a radical chosen from the following radicals: C 3 H 6 , C 4 H 8 , C5H10, C 6 Hi 2 , H 2 C-(CH 2 OCH2)6-CH2, H2C-(CH20CH2)i 3"CH2, H2C-(CH20CH2) 4 5-CH2 or H2C-CeH 4 -CH2.
  • the polyols of the invention are used to prepare polymers, for example by reaction with isocyanates.
  • the isocyanate in particular IPDI or HMDI
  • this protocol was applied using as polyol the diol (8) of Example 2 and by varying the nature of the isocyanate (IPDI and HMDI), and also the reaction time and the OH/NCO ratio.
  • the catalyst used is DBTDL (dibutyltin dilau- rate) at 0.1 % by weight.
  • Table 1 corresponds to the synthesis of polyurethane by reaction with IPDI (iso- phorone diisocyanate):
  • Mw weight-average molecular mass, determined by steric exclusion chromatography (THF solvent, polystyrene calibration, IR detection)
  • Viscosity (cSt) dynamic viscosity determined on a Brookfield AR2000 rheome- ter.
  • Table 2 corresponds to the synthesis of polyurethane by reaction with HMDI (hexamethylene diisocyanate):
  • All the polymers are soluble in dichloromethane, tetrahydrofuran and dimethylfor- mamide, to a proportion of at least 10 g per litre.
  • Example 7 Preparation of polyols and polymers 1 / Preparation of polyols according to the invention
  • the process is performed in the same manner for the other two polyols.
  • the desired polymer is obtained, which is analysed by steric exclusion chromatography. The following results are obtained:
  • a liquid lipstick is prepared, comprising (weight%):
  • the polymer is dissolved in the castor oil and the octyldodecanol at 100°C, followed by addition of the pigments.
  • the whole is then mixed using a deflocculating turbomixer (Rayneri).
  • a glossy liquid lipstick with good staying power is obtained.
  • a stick of lipstick comprising (weight%):
  • Example 10 The wax and the polymer are dissolved in the castor oil and the Parleam at 100°C, followed by addition of the pigments. The whole is then mixed using a deflocculating turbomixer (Rayneri) and then poured into lipstick moulds. A stick of glossy lipstick with good staying power is obtained.
  • a deflocculating turbomixer Rayneri
  • a lip gloss is prepared, comprising (weight%):
  • the polymer is mixed in the castor oil at 100°C, followed by addition of the pigments.
  • the whole is then mixed using a deflocculating turbomixer (Rayneri).
  • Rayneri a deflocculating turbomixer

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  • Public Health (AREA)
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  • General Health & Medical Sciences (AREA)
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  • Pharmacology & Pharmacy (AREA)
  • Emergency Medicine (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Polyurethanes Or Polyureas (AREA)
  • Cosmetics (AREA)

Abstract

Composition cosmétique, dermatologique, dermocosmétique, orale cosmétique ou nutraceutique comprenant un polymère pouvant être obtenu par polymérisation de diisocyanate et de polyol représenté par la formule (I"): (I") dans laquelle -R'1 représente un radical H ou un groupe alkyle en C2-C19 ; -A1 représente un radical alkylène en C2-C18 ; R’’ représente un groupe alkyle en C1-C18 ou un groupe -A2-OH, A2 représentant un radical alkylène divalent en C1-C10 éventuellement substitué ; et -R3 représente un alkyle en C1-C18 ou un groupe -A2-O-Y'. L’invention concerne également une méthode de traitement cosmétique au moyen de ladite composition.
PCT/EP2010/062624 2009-09-11 2010-08-30 Composition comprenant un polymère basé sur des polyols particuliers, et méthode de traitement cosmétique Ceased WO2011029738A1 (fr)

Applications Claiming Priority (4)

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FR0956235A FR2949973B1 (fr) 2009-09-11 2009-09-11 Composition cosmetique ou dermatologique comprenant un polymere a base de polyols particuliers, et procede de traitement cosmetique
FR0956235 2009-09-11
US24326009P 2009-09-17 2009-09-17
US61/243,260 2009-09-17

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20130005937A1 (en) * 2009-09-11 2013-01-03 Centre National De La Recherche Scientifique (C.N.R.S.) Novel method for preparing polyols and products obtained
CN107207691A (zh) * 2014-12-04 2017-09-26 路博润先进材料公司 含有机相的组合物的粘度改性

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE4308097A1 (de) * 1993-03-15 1994-09-22 Henkel Kgaa Polyol für ein Isocyanat-Gießharz und Beschichtungen
US5707612A (en) 1996-04-08 1998-01-13 Alzo, Inc. Use urethane polymers of castor oil skin and personal care product compositiions
FR2782723A1 (fr) 1998-08-27 2000-03-03 Atochem Elf Sa Formulations polyurethane a base de polybutadiene hydroxyle catalysees par un derive de l'imidazole
EP1097699A1 (fr) 1999-11-04 2001-05-09 L'oreal Composition cosmétique contenant un ester d'acide gras hydroxyle
FR2831431A1 (fr) * 2001-10-26 2003-05-02 Oreal Composition cosmetique colorante comprenant un polycondensat a groupes fluores
WO2009058368A1 (fr) * 2007-11-01 2009-05-07 Cargill, Incorporated Polyols de polyester dérivés d'huile naturelle et polyuréthanes obtenus à partir de ceux-ci

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE4308097A1 (de) * 1993-03-15 1994-09-22 Henkel Kgaa Polyol für ein Isocyanat-Gießharz und Beschichtungen
US5707612A (en) 1996-04-08 1998-01-13 Alzo, Inc. Use urethane polymers of castor oil skin and personal care product compositiions
FR2782723A1 (fr) 1998-08-27 2000-03-03 Atochem Elf Sa Formulations polyurethane a base de polybutadiene hydroxyle catalysees par un derive de l'imidazole
EP1097699A1 (fr) 1999-11-04 2001-05-09 L'oreal Composition cosmétique contenant un ester d'acide gras hydroxyle
FR2831431A1 (fr) * 2001-10-26 2003-05-02 Oreal Composition cosmetique colorante comprenant un polycondensat a groupes fluores
WO2009058368A1 (fr) * 2007-11-01 2009-05-07 Cargill, Incorporated Polyols de polyester dérivés d'huile naturelle et polyuréthanes obtenus à partir de ceux-ci

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20130005937A1 (en) * 2009-09-11 2013-01-03 Centre National De La Recherche Scientifique (C.N.R.S.) Novel method for preparing polyols and products obtained
US9556403B2 (en) * 2009-09-11 2017-01-31 Centre National De La Recherche Scientifique Method for preparing polyols and products obtained
CN107207691A (zh) * 2014-12-04 2017-09-26 路博润先进材料公司 含有机相的组合物的粘度改性

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FR2949973B1 (fr) 2012-08-10

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