WO2011154508A1 - Composition cosmétique comprenant un polymère et un dérivé de 4-carboxy-2-pyrrolidinone, composé et procédé de traitement cosmétique - Google Patents

Composition cosmétique comprenant un polymère et un dérivé de 4-carboxy-2-pyrrolidinone, composé et procédé de traitement cosmétique Download PDF

Info

Publication number
WO2011154508A1
WO2011154508A1 PCT/EP2011/059630 EP2011059630W WO2011154508A1 WO 2011154508 A1 WO2011154508 A1 WO 2011154508A1 EP 2011059630 W EP2011059630 W EP 2011059630W WO 2011154508 A1 WO2011154508 A1 WO 2011154508A1
Authority
WO
WIPO (PCT)
Prior art keywords
weight
acid
polymer
group
linear
Prior art date
Application number
PCT/EP2011/059630
Other languages
English (en)
Inventor
Gérard Malle
Céline Farcet
Hervé Richard
Original Assignee
L'oreal
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by L'oreal filed Critical L'oreal
Publication of WO2011154508A1 publication Critical patent/WO2011154508A1/fr

Links

Classifications

    • 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
    • A61K8/4906—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
    • A61K8/4913—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having five membered rings, e.g. pyrrolidone carboxylic acid
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
    • C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D207/24—Oxygen or sulfur atoms
    • C07D207/26—2-Pyrrolidones
    • C07D207/273—2-Pyrrolidones with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to other ring carbon atoms
    • C07D207/277—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/52—Stabilizers
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q3/00—Manicure or pedicure preparations
    • A61Q3/02—Nail coatings

Definitions

  • Cosmetic composition comprising a polymer and a 4-carboxy-2- pyrrolidinone derivative, cosmetic treatment process and compound
  • the present invention relates to novel cosmetic compositions comprising compounds of 4-carboxy-2-pyrrolidinone ester derivative type and polymers, of natural or synthetic origin.
  • cosmetic or dermatological products comprise a liquid fatty phase and are provided in varied galenical forms, such as dispersions, oily lotions, oil/water, water/oil or multiple emulsions, cream gels or sticks.
  • Certain particularly advantageous cosmetic or dermatological ingredients are not readily soluble, or even conveyable, in the oily phase of these formulations and have a tendency during storage to form crystals or to precipitate, in particular in emulsions.
  • polymers in cosmetically acceptable media since said polymers are generally less soluble than molecules of lower molecular weight.
  • polymers can result in solutions that are very viscous, thereby limiting the concentration at which they can be used in formulation. This is even more critical for polymers of natural origin and derivatives thereof, for which there are only a few cosmetically acceptable media for conveying them.
  • conveying synthetic polymers or polymers of natural origin at significant levels in cosmetically acceptable media remains a real challenge, whether in solution, in dispersion or in emulsion.
  • Pyrrolidinone derivatives are known as penetrating agents for active agents such as oleocanthal in application WO 2008/01240 or such as asprotadil alkyl esters in patent US 6 673 841 .
  • active agents such as oleocanthal in application WO 2008/01240 or such as asprotadil alkyl esters in patent US 6 673 841 .
  • a subject of the present invention is therefore a cosmetic composition comprising, in a cosmetically acceptable medium,
  • - Ri denotes a hydrogen atom or a linear C1-C20 or branched C3-C20 alkyl radical
  • - R2 denotes a linear C1-C20 or branched C3-C20 alkyl radical which can contain a
  • C5-C6 ring a C5-C6 cycloalkyl radical optionally substituted with one or two methyl radicals; the phenyl radical, the benzyl radical or the phenethyl radical;
  • R3 and R 4 denote, independently of one another, a hydrogen atom, or a linear C1-C12 or branched C3-C12 alkyl radical;
  • the compounds of formula (I) can be incorporated into many cosmetic products. They can also be incorporated into aqueous or solvent-based compositions in particular used in the paint, varnish, glue and adhesive, cement and coating, and domestic cleaning and hygiene product fields, for example.
  • these compounds exhibit excellent compatibility with the customary cosmetic media and are therefore very easy to use for the formulator.
  • the dissolving, dispersing or emulsifying of polymers is therefore facilitated in the presence of the compounds according to the invention.
  • the compounds according to the invention make it possible to obtain improved spreading of the formula on the skin and skin appendages, which is reflected by a uniform deposit and an aesthetic final effect.
  • Another advantage of these compounds lies in the fact that they can make it possible to compatibilize polymers which require different formulations, or even formulations which are not very compatible.
  • the use of the compounds according to the invention makes it possible to prepare a composition comprising both (i) a polymer A that can be formulated in short esters, C3-C8 esters for example, such as butyl acetate, which are insoluble or have low solubility in oily phases, and (ii) a polymer B which is itself conveyable (soluble or dispersible) in oily media and has very low solubility in said short esters.
  • a polymer A that can be formulated in short esters
  • C3-C8 esters for example, such as butyl acetate
  • a polymer B which is itself conveyable (soluble or dispersible) in oily media and has very low solubility in said short esters.
  • - Ri denotes a hydrogen atom or a linear C1-C20 or branched C3-C20 alkyl radical
  • - R2 denotes a linear C1-C20 or branched C3-C20 alkyl radical which can contain a C5-C6 ring; a C5-C6 cycloalkyl radical optionally substituted with one or two methyl radicals; the phenyl radical, the benzyl radical or the phenethyl radical; - R3 and R 4 denote, independently of one another, a hydrogen atom, or a linear C1-C12 or branched C3-C12 alkyl radical;
  • formula (I) among the alkyl groups, mention may in particular be made of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-octyl, 2-ethyl- hexyl, dodecyl, hexadecyl, cyclohexyl or methylcyclohexyl groups.
  • the salts of the compounds described in the present invention comprise the conventional nontoxic salts of said compounds, such as those formed from cosmetically acceptable organic or inorganic acids or bases. Mention may be made of ammonium salts, alkanolamine salts such as triethanolamine salts, aminopropanediol salts, and salts of alkali metals or alkaline-earth metals, such as sodium, potassium, magnesium and calcium.
  • R 3 and R 4 are hydrogen.
  • Ri denotes a hydrogen atom or a linear C1-C18 or branched C3-C18 alkyl radical; and better still a linear C2-C18 or branched C3-C10 alkyl radical.
  • R2 denotes a linear C2-C18 or branched C3-C18 alkyl radical; and better still a linear C3-C16 or branched C3-C12 alkyl radical; or a cyclohexyl, phenyl, benzyl or phenethyl radical; most preferably, R2 denotes a linear C 4 -Cio or branched C 4 -Cio alkyl radical; such as butyl and 2-ethylhexyl.
  • the counterions indicated can be replaced by any organic or inorganic, cosmetically acceptable cationic counterion, preferably chosen from inorganic cations of alkali metals or alkaline-earth metals, such as Na, Mg, K and Ca, and organic cations such as ammonium NR + , with R, which may be identical or different, representing H or a C1 -C6 (hydroxy)alkyl.
  • organic cations such as ammonium NR + , with R, which may be identical or different, representing H or a C1 -C6 (hydroxy)alkyl.
  • the compounds which are even more preferred are the compounds of formulae (I), (n), (o), (ac), (am), (at), (au), (av), (ba), (bg), (bl), (bm), (bp), (br), (bw) and (bx).
  • the compounds of formula (I) can be obtained according to the syntheses described in the following articles: J. Org. Chem., 26, pages 1519-24 (1961 ); Tetrahedron Asymmetric, 12 (23), pages 3241 -9 (2001 ); J. Industrial & Engineering Chem., 47, pages 1572-8 (1955); J. Am. Chem. Soc, 60, pages 402-6 (1938); and in patents EP0069512, US281 1496, US2826588, US3136620, FR2290199 and FR2696744.
  • the compounds of formula (I) are preferably present, alone or as a mixture, in the cosmetic compositions according to the invention in an amount of from 0.5% to 40% by weight, better still from 1 % to 30% by weight, or even 2% to 25% by weight, and preferentially from 3% to 20% by weight, relative to the total weight of the composition.
  • the cosmetic composition according to the invention also comprises at least one polymer.
  • This polymer may be of natural origin, and optionally modified, or may be synthetic.
  • polymer is intended to mean a material resulting from the covalent linking of a large number of identical or different monomer units, which can be in the form of a more or less viscous liquid, or in the form of a solid, at ambient temperature (25°C).
  • a polymer preferably comprises at least 5 identical or different repeating units.
  • the weight-average molecular weight (Mw) of said polymer is between 2000 and 2 000 000, in particular between 5000 and 1 000 000, or even between 10 000 and 500 000, even better still between 20 000 and 300 000, preferentially between 30 000 and 200 000, and even better still between 40 000 and 180 000.
  • synthetic polymer is intended to mean a polymer that can be prepared from identical or different monomers by means of a customary polymerization process, such as radical polyaddition, ionic polyaddition, polycondensation or else ring opening.
  • natural polymer or polymer of natural origin is intended to mean a polymer produced/synthesized by live beings (plants, animas, microorganisms) or a polymer resulting from fermentation by bacteria (biotechnology) in its native state; said polymer may have undergone one or more subsequent chemical transformation(s), such as, for example, a hydrolysis, an esterification, an etherification or a succinylation; the term “modified natural polymers” will then be used.
  • the polymers that can be used in the context of the present invention may be linear or branched, grafted or comb, hyperbranched or dendrimer, or even partially crosslinked, polymers; they may be random, alternating, block, or even gradient polymers; they may be homopolymers or copolymers.
  • the polymers may be vinyl polymers, block polymers, polymers that have been surface-stabilized and polycondensates.
  • the polymers that can be used in the context of the present invention may be vinyl polymers, i.e. resulting from the polymerization of monomers comprising an ethylenic unsaturation (vinyl monomers).
  • - a linear or branched, saturated or unsaturated alkyl group containing 1 to 22 carbon atoms, in particular 4 to 20, or even 6 to 18 carbon atoms, which can optionally comprise, inserted and/or as a substitution, one or more heteroatoms chosen from O, N, S, P and halogen atoms (CI, Br, I and F);
  • R 3 may be a methyl, ethyl, propyl, n-butyl, isobutyl, tert-butyl, hexyl, ethylhexyl, octyl, lauryl, isooctyl, isodecyl, dodecyl, behenyl, stearyl or 2-ethyl- perfluorohexyl group; or a Ci-C 4 hydroxyalkyl group such as 2-hydroxyethyl, 2-hydroxybutyl and 2-hydroxypropyl; or a (Ci-C 4 )alkoxy(Ci-C 4 )alkyl group such as methoxyethyl, ethoxyethyl and methoxypropyl,
  • cycloalkyl group such as the isobornyl, cyclohexyl or t-butylcyclohexyl group,
  • aralkyl group (Ci to Cs alkyl group), such as 2-phenylethyl, t-butylbenzyl or benzyl,
  • heterocyclic group of 4 to 12 ring members containing one or more heteroatoms chosen from O, N and S, the ring being aromatic or nonaromatic, - a heterocycloalkyl group (Ci to C 4 alkyl), such as furfuryl methyl or tetrahydrofurfuryl methyl,
  • cycloalkyl, aryl, aralkyl, heterocyclic or heterocycloalkyl groups to be optionally substituted with one or more substituents chosen from hydroxyl groups, halogen atoms, and linear or branched Ci-C 4 alkyl groups, which can optionally comprise, inserted and/or as a substitution, one or more heteroatoms chosen from O, N, S, P and halogen atoms (CI, Br, I and F);
  • - a linear or branched, saturated or unsaturated alkyl group containing 1 to 22 carbon atoms, in particular 4 to 20, or even 6 to 18 carbon atoms, which can optionally comprise, inserted and/or as a substitution, one or more heteroatoms chosen from O, N, S, P and halogen atoms (CI, Br, I and F);
  • R 6 and/or R 7 can be a methyl, ethyl, propyl, n-butyl, isobutyl, tert-butyl, hexyl, ethylhexyl, octyl, lauryl, isooctyl, isodecyl, dodecyl, behenyl, stearyl or 2-ethylperfluorohexyl group; or a Ci-C 4 hydroxyalkyl group such as 2-hydroxyethyl, 2-hydroxybutyl and 2-hydroxypropyl; or a (Ci-C 4 )alkoxy(CrC 4 )alkyl group such as methoxyethyl, ethoxyethyl and methoxypropyl;
  • cycloalkyl group such as the isobornyl, cyclohexyl or t-butylcyclohexyl group;
  • a C 4 to C30 aralkyl group (Ci to Cs alkyl group), such as 2-phenylethyl, t-butylbenzyl or benzyl;
  • heterocyclic group of 4 to 12 ring members containing one or more heteroatoms chosen from O, N and S, the ring being aromatic or nonaromatic;
  • heterocycloalkyl group such as furfuryl methyl or tetrahydrofurfurylmethyl
  • cycloalkyl, aryl, aralkyl, heterocyclic or heterocycloalkyl groups to be optionally substituted with one or more substituents chosen from hydroxyl groups, halogen atoms, and linear or branched Ci-C 4 alkyl groups, which can optionally comprise, inserted and/or as a substitution, one or more heteroatoms chosen from O, N, S, P and halogen atoms (CI, Br, I and F);
  • - a linear or branched alkyl group containing from 1 to 22 carbon atoms, in particular 4 to 20, or even 6 to 18 carbon atoms, which can optionally comprise, inserted and/or as a substitution, one or more heteroatoms chosen from O, N, S, P and halogen atoms (CI, Br, I and F);
  • Ci 2 cycloalkyl group such as isobornyl or cyclohexyl
  • aralkyl group (Ci to Cs alkyl group), such as 2-phenylethyl or benzyl;
  • heterocyclic group of 4 to 12 ring members containing one or more heteroatoms chosen from O, N and S, the ring being aromatic or nonaromatic; - a heterocycloalkyl group (Ci-C 4 alkyl), such as furfuryl methyl or tetrahydrofur- furyl methyl,
  • cycloalkyl, aryl, aralkyl, heterocyclic or heterocycloalkyl groups to be optionally substituted with one or more substituents chosen from hydroxyl groups, halogen atoms and linear or branched Ci-C 4 alkyl groups, which can optionally comprise, inserted and/or as a substitution, one or more heteroatoms chosen from O, N, S, P and halogen atoms (CI, Br, I and F);
  • -(v) monomers comprising one or more ethylenic unsaturation(s) and comprising at least one carboxylic, phosphoric or sulphonic acid function, for instance acrylic acid, methacrylic acid, crotonic acid, itaconic acid, fumaric acid, maleic acid, acrylamidopropanesulphonic acid, vinylbenzoic acid, vinylphosphoric acid and the salts thereof; or maleic anhydride;
  • - n is an integer from 1 to 10, preferably equal to 1 or 3;
  • Rg denotes a linear or branched, preferably linear, C1-C10 divalent hydrocarbon- based group optionally containing one or two ether -O- bonds; preferably ethylene, propylene or butylene;
  • R10 denotes a linear or branched, C1-C10, in particular C Cs, alkyl group, preferably methyl, ethyl, propyl, butyl or pentyl;
  • - n denotes an integer from 1 to 300, preferably from 3 to 200, and preferentially from 5 to 100;
  • - n is an integer from 1 to 10, preferably equal to 1 , 2, 3 or 4;
  • R'2, R M 2, R'3 and R M 3 which may be identical or different, represent a C1-C10 alkyl group, preferably methyl or ethyl;
  • R3 is a C2-C10, preferably C or C3, divalent alkylene group
  • X(i) which may be identical or different, represents a -R4-Si-[O-(R'3)(R M 3)-X(i-1 )]3 group, with R4, which may be identical or different, representing a C to C10, preferably C or C3, divalent alkylene group;
  • H 2 C :C-C l l-0-C 3,H fi 6— Si- -0-Si-C 2 H 4 - -SiH-O-Si— C 2 H— Si-hO-Si-CH 3 o CH, CH, CH 3 '3
  • R which may be identical or different, is a linear C1-C10 alkyl group, preferably methyl, or a cyclic C3-C12, preferably C 5 , alkyl group.
  • the salts may be formed by neutralization of the anionic groups using an inorganic base, such as LiOH, NaOH, KOH, Ca(OH) 2 , NH 4 OH or Zn(OH) 2 ; or with an organic base such as a primary, secondary or tertiary alkylamine, in particular triethylamine or butylamine.
  • This primary, secondary or tertiary alkylamine may comprise one or more nitrogen and/or oxygen atoms and may thus comprise, for example, one or more alcohol functions; mention may in particular be made of 2-amino-2-methylpropanol, triethanolamine and dimethylamino-2-propanol. Mention may also be made of lysine or 3-(dimethylamino)propylamine.
  • inorganic acids such as sulphuric acid, hydrochloric acid, hydrobromic acid, hydriodic acid, phosphoric acid or boric acid.
  • the polymers may be solubilized or dispersed in the medium, in particular the organic medium, comprising at least one compound of formula (I), or even in the cosmetically acceptable medium.
  • the term "solubilized” is intended to mean that the polymer is dissolved in the medium, without modification of pH, at a content with respect to dry matter of 5% by weight, at ambient temperature (25°C, 1 atm.). It is considered that the polymer is soluble if it does not form a precipitate or agglomerate visible to the eye, when it is dissolved, and it therefore produces a clear solution.
  • dispersed or “made into a dispersion” is intended to mean that the polymer forms, in the organic medium, at 25°C, 1 atm., a stable dispersion, preferably of particles having a size of 20 - 500 nm, with a dry matter content of 5- 50% by weight.
  • the polymer that can be used in the context of the invention is a block polymer comprising at least one first block and at least one second block, which preferably have different glass transition temperatures (Tg). It is specified that the terms “first” and “second” blocks do not in any way condition the order of said blocks in the structure of the polymer.
  • the first and second blocks have different glass transition temperatures, with a difference of generally more than 5°C, preferably more than 10°C, and better still more than 20°C.
  • said block ethylenic polymer is linear, branched or grafted; preferably, it does not comprise any multifunctional monomer or compound, added deliberately, which is capable of generating branches and/or crosslinks.
  • said blocks are mutually incompatible.
  • mutant blocks is intended to mean that the mixture formed from the polymer corresponding to the first block and from the polymer corresponding to the second block is immiscible in the polymerization solvent present in weight majority for the block polymer, at ambient temperature (25°C) and atmospheric pressure (10 5 Pa), for a content of the polymer mixture of greater than or equal to 5% by weight, relative to the total weight of the mixture (polymers and solvent), it being understood that:
  • said polymers are present in the mixture in a content such that the respective weight ratio ranges from 10/90 to 90/10, and that
  • each of the polymers corresponding to the first and second blocks has an average (weight-average or number-average) molecular weight equal to that of the block polymer +/- 15%.
  • said blocks may be connected together via an intermediate segment comprising at least one constituent monomer ml of the first block and at least one constituent monomer m2 of the second block.
  • said intermediate segment forms an intermediate block.
  • m2 is different from ml .
  • Said intermediate segment or block may in particular allow these first and second blocks to be "compatibilized”.
  • the intermediate segment or block comprising at least one constituent monomer of the first block and at least one constituent monomer of the second block of the polymer is a random polymer.
  • said intermediate segment or block is derived essentially from constituent monomers of the first block and of the second block.
  • the term "essentially” is intended to mean at least 85%, preferably at least 90%, better still 95% and even better still 100%.
  • said block polymer is film-forming.
  • it comprises two blocks (diblock) or three blocks (triblock).
  • Each block of the polymer according to the invention is derived from one type of monomer or from several different types of monomers. This means that each block can consist of a homopolymer or a copolymer, which may be random, alternating, or the like.
  • the block polymer according to the invention preferably comprises at least one block having a Tg of greater than or equal to 20°C and one block having a Tg strictly below 20°C.
  • one of the blocks has a Tg of between 20°C and 160°C, in particular between 40°C and 120°C, preferentially between 50°C and 1 10°C.
  • one of the blocks has a Tg of between -150°C and 20°C (excluded), in particular between -100°C and 10°C, preferentially between -50°C and 0°C.
  • the block having the highest Tg is in majority amount, by weight, relative to the other blocks.
  • the block polymer according to the invention consists exclusively of a first block and a second block (it is then a diblock polymer), or exclusively of a first block, a second block and an intermediate segment which is preferably an intermediate block (which may thus be a triblock polymer).
  • the block having the highest Tg may be present in the block polymer in an amount of from 50% to 90% by weight, in particular from 55% to 80% and even better still from 60% to 75% by weight, relative to the total weight of the block polymer, and the second block may be present in an amount of from 10% to 50% by weight, in particular 20% to 45% by weight and even better still from 25% to 40% by weight, relative to the total weight of the block polymer.
  • the block having the highest Tg may be present in the block polymer in an amount of from 45% to 90% by weight, in particular 50% to 80% and even better still from 55% to 75% by weight, relative to the total weight of the block polymer;
  • the second block may be present in an amount of from 9% to 45% by weight, in particular 10% to 40% by weight and even better still from 20% to 35% by weight, relative to the total weight of the block polymer;
  • the intermediate segment or block may represent 1 % to 10% by weight, in particular 2% to 7% by weight and even better still 3% to 5% by weight, relative to the total weight of the block polymer.
  • said first and/or second blocks may consist of a homopolymer or a copolymer, which may be random, alternating or the like, preferably random.
  • the chemical nature and/or the amount of the monomers constituting each of the blocks may obviously be chosen by those skilled in the art, on the basis of their general knowledge, to obtain blocks that have the required Tgs.
  • the monomers constituting all or part of said blocks, in particular of the first and/or second blocks can be chosen from, alone or as a mixture, the monomers mentioned above (families (i) to (v)).
  • they are chosen from, alone or as a mixture,
  • Ri represents an unsubstituted, linear or branched, C 1 -C 12 alkyl group or a C 4 to C 12 cycloalkyl group;
  • R 2 represents an unsubstituted, linear or branched, Ci to C 12 alkyl group, or a C 4 to C 12 cycloalkyl group such as an isobornyl group;
  • R' representing H or CH 3
  • R 7 and R 8 which may be identical or different, represent a hydrogen atom or a linear or branched Ci to C 12 alkyl group, such as an n-butyl, t-butyl, isopropyl, isohexyl, isooctyl or isononyl group; or else R 7 represents H and R represents a 1 ,1 -dimethyl-3-oxobutyl group;
  • R 5 represents a linear or branched C 4 to C12 alkyl group
  • N-(C 4 -Ci2 alkyl)acrylamides such as N-octylacrylamide.
  • the monomers are chosen from, alone or as a mixture:
  • Ci-C 4 alkyl or C3-C12 cycloalkyl methacrylates and in particular methyl methacrylate, isobornyl methacrylate and isobutyl methacrylate;
  • the weight-average molecular weight (Mw) of the block polymer according to the invention is preferably between 25 000 and 1 000 000, better still between 30 000 and 750 000, or even between 40 000 and 500 000, and preferentially between 50 000 and 250 000.
  • the weight-average (Mw) and number-average (Mn) molecular weights are determined by gel permeation liquid chromatography (solvent THF, calibration curve established with linear polystyrene standards, refractometric and UV detector).
  • the polydispersity index of said block polymer is greater than 2, for example ranging from 2 to 9, preferably greater than or equal to 2.5, for example ranging from 2.5 to 8, and better still ranging from 2.8 to 7.
  • the polydispersity index PI of the polymer is equal to the ratio of the weight-average molecular weight Mw to the number-average molecular weight Mn.
  • Said block polymer may in particular be prepared according to the processes described in applications EP141 1069 and EP1882709.
  • the polymer that can be used in the context of the invention is an acrylic polymer comprising a backbone that is advantageously insoluble in an organic medium and a part that is advantageously soluble in said medium, said part consisting of side chains covalently bonded to said backbone, said polymer being capable of being obtained by radical polymerization, in said organic medium:
  • macromonomers comprising an end group capable of reacting during the polymerization so as to form the side chains, said macromonomer(s) having a weight-average molecular weight of greater than or equal to 200;
  • said optionally soluble part representing 0.05% to 20% by weight of the polymer, said polymer having a weight-average molecular weight ranging from 10 000 to 300 000.
  • the acrylic polymer has a weight-average molecular weight (Mw) of from 20 000 to 200 000, even better still from 25 000 to 150 000.
  • Mw weight-average molecular weight
  • the acrylic polymers may be in various forms, in particular in the form of random polymers.
  • the choice of the constituent monomers of the backbone of the polymers, and of the macromonomers, like the size of the polymer and of the side chains and also the proportion of the side chains, will be made according to the desired properties, and in particular according to the organic medium, so as to be able to obtain, if desired, a dispersion of polymer particles that is stable in said medium, it being possible for this choice to be made by those skilled in the art.
  • acrylic monomers capable of constituting, after polymerization, the backbone of said polymer
  • R 6 represents a linear or branched C1-C6 alkyl group or a C3-C6 cycloalkyl group or an aromatic group, for example of benzene, anthracene and naphthalene type;
  • - monomers comprising one or more ethylenic unsaturation(s) and comprising at least one carboxylic or sulphonic acid function, such as acrylic acid, methacrylic acid, crotonic acid, maleic anhydride, itaconic acid, fumaric acid, maleic acid, styrenesulphonic acid, acrylamidopropanesulphonic acid, vinylbenzoic acid, vinylphosphoric acid and the salts thereof;
  • - monomers comprising one or more ethylenic unsaturation(s) and comprising at least one tertiary amine function, such as 2-vinylpyridine, 4-vinylpyridine, dimethylaminoethyl methacrylate, diethylaminoethyl methacrylate, dimethylaminopropylmethacrylamide and the salts thereof.
  • the macromononners constituting, after reaction, the side chains of the acrylic polymer comprise an end group capable of reacting, during the polymerization, with the acrylic monomers or the growing backbone so as to form said chains. This end group may be an ethylenically unsaturated group, in particular a (meth)acryloyl group.
  • macromonomers that can be used, mention may be made of:
  • polyolefins comprising a (meth)acryloyl end group, such as those based on polyethylene, polypropylene, polyethylene-polypropylene, polyethylene- polybutylene, polyisoprene, polybutadiene or poly(ethylene/butylene)- polyisoprene, and more particularly the poly(ethylene/butylene) methacrylate sold under the name Kraton Liquid L-1253 by Kraton Polymers;
  • polydimethylsiloxanes such as the methacryloyloxypropylpolydimethylsiloxanes sold under the name PS560-K6 by UCT or under the name MCR-M17 by Gelest Inc.
  • the particularly advantageous polymers are those obtained by polymerization: - of methyl acrylate and of the polyethylene/polybutylene macromer (Kraton L-1253), in particular in isododecane; or
  • Said acrylic polymer is therefore preferably a polymer obtained by radical polymerization between:
  • the homopolymer or the corresponding copolymers of which are insoluble in the organic medium under consideration i.e. the homopolymer or the copolymers mentioned above are in solid (or undissolved) form at a concentration of greater than or equal to 5% by weight at ambient temperature in said nonaqueous organic medium;
  • the homopolymer or the corresponding random copolymers of which are soluble in the organic medium under consideration i.e. the abovementioned homopolymer or copolymers are completely dissolved at a concentration of greater than or equal to 5% by weight at ambient temperature in said nonaqueous organic medium.
  • Organic medium' is intended to mean a medium consisting of one or more nonaqueous compounds, it being possible for said medium to contain at most 1 % by weight of water.
  • the term 'macromonomer' is intended to mean any oligomer comprising, on one of its ends, an end group capable of reacting during the polymerization reaction so as to form the side chains, it being possible for said group to be a group with an ethylenic unsaturation capable of polymerizing, via radical polymerization, with the acrylic monomers, or a reactive functional group capable of reacting with the acrylic monomers or else with the backbone undergoing formation during the polymerization.
  • said acrylic polymers are preferably in the form of insoluble polymers comprising a backbone (or main chain) constituted of a sequence of acrylic units resulting from the polymerization of one or more acrylic monomers and comprising side chains (or grafts) resulting from the reaction of the macromonomers, said side chains being covalently bonded to said backbone (or main chain).
  • the backbone (or main chain) is insoluble in the organic medium under consideration, whereas the side chains (or grafts) are soluble in said medium.
  • the polymers may have the ability, in a given organic medium, to fold over on themselves, thus forming particles of substantially spherical shape, the periphery of these particles having the deployed side chains, which ensure the stability of these particles.
  • Such particles have the particularity of not aggregating in said medium and therefore of being self-stabilized and of forming a particularly stable polymer particle dispersion in said medium.
  • stable dispersion is intended to mean, according to the invention, a dispersion which is not capable of forming a solid deposit, or of liquid/solid phase separation, in particular after centrifugation, for example at 4000 rpm for 15 minutes.
  • the polymers of the invention are capable of forming particles having an average size ranging from 10 to 400 nm, preferably from 20 to 200 nm, in an organic medium under consideration.
  • the part constituted of the side chains according to the invention represents 0.1 % to 15%, even more preferentially from 0.1 % to 10%, or even better still from 0.2% to 10% of the total weight of the polymer.
  • the macromonomers according to the invention have a weight-average molecular weight ranging from 200 to 20 000, preferably from 500 to 15 000.
  • the polymers can form a dispersion of particles in a nonaqueous organic medium; these particles are individual and self-stabilized, and do not form particle aggregates and insoluble sediments after the dispersion has been left to stand, for example, for a day at ambient temperature.
  • the organic medium is a liquid medium consisting of at least one nonaqueous liquid compound and can be defined relative to the Hansen global solubility parameter ⁇ .
  • ⁇ (d D 2 + dp 2 + d H 2 ) 1 2 in which: - CJD characterizes the LONDON dispersion forces arising from the formation of dipoles induced during molecular impacts;
  • the organic medium may consist of at least one liquid compound chosen from the group constituted of, alone or as a mixture:
  • liquid fatty substances in particular oils, which may be chosen from natural or synthetic, carbon-based, hydrocarbon-based, fluoro and/or silicone oils, which are optionally branched, alone or as a mixture.
  • oils mention may be made of plant oils formed from fatty acid esters of polyols, in particular triglycerides, such as sunflower oil, sesame oil or rapeseed oil, or esters derived from acids or alcohols containing a long chain (i.e.
  • esters of formula RCOOR' in which R represents a higher fatty acid residue containing from 7 to 19 carbon atoms and R' represents a hydrocarbon-based chain containing from 3 to 20 carbon atoms, such as palmitates, adipates and benzoates, in particular diisopropyl adipate.
  • RCOOR' in which R represents a higher fatty acid residue containing from 7 to 19 carbon atoms and R' represents a hydrocarbon-based chain containing from 3 to 20 carbon atoms, such as palmitates, adipates and benzoates, in particular diisopropyl adipate.
  • Mention may also be made of linear, branched and/or cyclic, optionally volatile, alkanes, and in particular liquid paraffin, liquid petroleum jelly, or hydrogenated polyisobutylene, isododecane, or else 'Isopars', volatile isoparaffins.
  • Mention may also be made of esters, ethers and ketones.
  • silicone oils such as polydimethylsiloxanes and polymethylphenylsiloxanes, optionally substituted with aliphatic and/or aromatic groups, which are optionally fluorinated, or with functional groups such as hydroxyl, thiol and/or amine groups, and volatile, in particular cyclic, silicone oils.
  • Mention may in particular be made of linear, branched or cyclic esters containing more than 6 carbon atoms; ethers containing more than 6 carbon atoms and ketones containing more than 6 carbon atoms.
  • the expression "monoalcohols" having a global solubility parameter in the Hansen solubility space of less than or equal to 20 (MPa) 1 2 is intended to mean aliphatic fatty monoalcohols containing at least 6 carbon atoms, the hydrocarbon-based chain comprising no substitution group.
  • monoalcohols according to the invention mention may be made of oleyl alcohol, decanol, dodecanol, octadecanol and linoleyl alcohol.
  • the organic medium under consideration contains, however, at least one 4-carboxy-2-pyrrolidinone derivative of formula (I) as defined above. This derivative, alone or as a mixture, may be the only constituent of the organic medium in which the acrylic polymer is dispersed; said medium may, however, also comprise a nonaqueous liquid compound as defined above.
  • said compound of formula (I) represents 1 % to 90% by weight, in particular 2% to 70% by weight, or even 5% to 50% by weight, of the organic medium in which said acrylic polymer is dispersed, the rest being constituted of the nonaqueous liquid compound(s).
  • the compound of formula (I) may, when it is used with at least one nonaqueous liquid compound, act as a codispersant for the acrylic polymer.
  • nonaqueous dispersion comprising a nonaqueous organic medium which comprises at least one compound of formula (I) and particles consisting of at least one acrylic polymer as defined above.
  • the polymer particles are in the form of nanometric particles, having an average size that can range from 10 to 400 nm, preferably from 20 to 200 nm. Owing to this very small size, the particles which go to make up the dispersion are particularly stable and therefore not very liable to form aggregates. Consequently, the dispersion of particles is a stable dispersion, in the nonaqueous organic medium under consideration, and does not form sediments, when it is placed for example at ambient temperature for a sustained period (for example 24 hours). Such dispersions can in particular be prepared according to the processes described in applications EP1428844 and EP1428843.
  • the polymer that can be used in the context of the invention is a polymer that has been surface-stabilized with a stabilizer.
  • the polymer described hereinafter can result in polymer particles of very small size, in particular nanometric size, which are generally spherical, in a dispersion in an organic medium.
  • the nanoparticles preferably have a size of between 5 and 600 m.
  • the polymers used may be of any nature. It is thus possible to use radical polymers, polycondensates, and polymers of natural origin, as defined above. These polymers may in particular be partially crosslinked.
  • CH 2 C(CH 3 )-COORi in which Ri represents an unsubstituted, linear or branched C1-C12 alkyl group or a C 4 to C12 cycloalkyl group;
  • - the acrylates of formula: CH 2 CH-COOR2 in which R 2 represents an unsubstituted, linear or branched Ci to C 12 alkyl group, or a C 4 to C 12 cycloalkyl group such as an isobornyl group;
  • CH 2 CR'-CO-NR 7 R 8 with R' representing H or CH 3 , and R 7 and R 8 , which may be identical or different, representing a hydrogen atom or a linear or branched Ci to C 12 alkyl group, such as an n-butyl, t-butyl, isopropyl, isohexyl, isooctyl or isononyl group; or else R 7 represents H and R 8 represents a 1 ,1 -dimethyl-3-oxobutyl group;
  • R 5 represents a linear or branched C 4 to C 12 alkyl group.
  • the polymer particles are surface-stabilized.
  • the particles can be surface-stabilized as the polymerization takes place, by virtue of a stabilizer which can in particular be a block polymer, a grafted polymer and/or a random polymer, alone or as a blend.
  • the stabilization can be carried out by any known means, and in particular by polymerization in the presence of the stabilizer.
  • the stabilizer is present in the mixture at the start of the polymerization.
  • the polymer in a second embodiment, can be synthesized in a synthesis solvent, and then dispersed in a nonaqueous dispersion medium by addition of the dispersant, and the synthesis solvent evaporated-off.
  • grafted-block or block copolymers comprising at least one block of polyorganosiloxane type and at least one block of a polymer (i) resulting from radical polymerization or (ii) resulting from polycondensation, in particular of polyether, polyester or polyamide type, or a mixture thereof, it being possible for said copolymer to comprise fluoro entities.
  • grafted-block or block copolymers comprising at least one block of polyorganosiloxane type and at least one block of a radical polymer
  • the polyorganopolysiloxane block may in particular be a polydimethylsiloxane or else a poly(C2-Ci8)alkylmethylsiloxane;
  • the polyether block may be a C2-C18 polyalkylene, in particular polyoxyethylene and/or polyoxypropylene. It is thus possible to use dimethicone copolyols or else (C2-Cis)alkyl methicone copolyols, which are optionally crosslinked.
  • dimethicone copolyol sold under the name Dow Corning 3225C by the company Dow Corning, or the lauryl methicone copolyol sold under the name Dow Corning Q2-5200 by the company Dow Corning. Mention may also be made of lauryl dimethicone copolyol crosspolymer, for example KSG31 or KSG32 from Shin-Etsu, cetyl dimethicone copolyol, such as DMC 3071 from GE, and dimethicone copolyol PPG-3-oleyl ether, such as KF-6026 from Shin Etsu;
  • block copolymers comprising at least one block A resulting from the polymerization of a nonacrylic ethylenic monomer, and at least one block B resulting from the polymerization of a vinyl monomer, in particular a (meth)acrylic, (meth)acrylamide or styrene monomer, or else polyether, polyester or polyamide, or mixtures thereof.
  • the nonacrylic ethylenic monomers may comprise one or more optionally conjugated ethylenic bonds, and in particular may be conjugated or unconjugated dienes.
  • the term "nonacrylic” is intended to mean without an acrylic or methacrylic group, including without an acrylate or methacrylate group. In particular, mention may be made of ethylene, butadiene, isobutylene and isoprene, and mixtures thereof.
  • the ethylenic monomer comprises several optionally conjugated ethylenic bonds, the residual ethylenic unsaturations after the polymerization are generally hydrogenated.
  • the polymerization of isoprene leads, after hydrogenation, to the formation of an ethylene-propylene block
  • the polymerization of butadiene leads, after hydrogenation, to the formation of an ethylene-butylene block.
  • the block A may therefore be of the polyethylene, polypropylene, polybutylene or polyisobutylene type, and copolymers thereof.
  • it When it is chosen from polyethers, it may be polyoxyethylene, polyoxypropylene and copolymers thereof.
  • the block B resulting from the polymerization of a vinyl monomer can in particular be a styrene polymer block.
  • block copolymers comprising a block resulting from the polymerization of a nonacrylic ethylenic monomer and a block of (meth)acrylic polymer such as poly(methyl methacrylate)
  • grafted-block or block copolymers comprising a block resulting from the polymerization of a nonacrylic ethylenic monomer and a block of polyether, such as a C2-C18 polyoxyalkylene, in particular polyoxyethylene and/or polyoxypropylene, mention may be made of polyoxyethylene/polybutadiene or polyoxyethylene/polyisobutylene diblock or triblock copolymers;
  • alkyl dimethicones in which the alkyl group contains 6 to 32 carbon atoms, such as lauryl methicone and stearyl methicone, in particular Si tec LDM 3107 from ISP, cetyl dimethicone such as Abil Wax 9801 , or behenoxy dimethicone such as Abil 5440 from Goldschmidt;
  • R is an alkyl radical containing 6 to 32 carbon atoms, such as dimethiconol behenate, and in particular the products Ultrabee from Noveon and Pecosil DB from Phoenix Chemical; - (g) alkylamidoamines containing in particular 6 to 60 carbon atoms, in particular 12 to 50, such as behenamidopropyldimethylamine, and in particular Catemol 220 from Phoenix Chemical, of formula:
  • the stabilizer is chosen from block copolymers comprising at least one block A resulting from the polymerization of a nonacrylic ethylenic monomer, and at least one block B resulting from the polymerization of a vinyl monomer, in particular a (meth)acrylic, (meth)acrylamide or styrene monomer, or else polyether, polyester or polyamide, or mixtures thereof.
  • Said polymers may thus be in the form of particles in a dispersion in an organic dispersion medium, as defined above.
  • Said organic medium may comprise nonaqueous liquid compounds which have a global solubility parameter in the Hansen solubility space of less than or equal to 17 (MPa) 1 2 , and/or monoalcohols which have a global solubility parameter in the Hansen solubility space of less than or equal to 20 (MPa) 1 2 .
  • the organic medium under consideration contains, however, at least one 4-carboxy-2-pyrrolidinone derivative of formula (I) as defined above.
  • This derivative alone or as a mixture, may be the only constituent of the organic medium in which the stabilized polymer is dispersed; said medium may, however, also comprise a nonaqueous liquid compound and/or a monoalcohol, as defined above.
  • said compound of formula (I) represents 1 % to 90% by weight, in particular 2% to 70% by weight, or even 5% to 50% by weight, of the organic medium in which said stabilized polymer is dispersed, the rest being constituted of the additional carbon-based/silicone-based compound(s).
  • the compound of formula (I) may, when it is used with at least one carbon-based compound, act as a codispersant for the polymer.
  • nonaqueous dispersion comprising an organic medium which comprises at least one compound of formula (I) and particles consisting of at least one polymer stabilized with a stabilizer as defined above.
  • Such dispersions may in particular be prepared according to the processes described in application EP749747. Dl
  • the polymer that can be used in the context of the invention is a copolymer which comprises at least one first block that is soluble in the organic medium and at least one second block that is insoluble in said medium.
  • the blocks are of homopolymer or gradient type.
  • the copolymer is of the 'diblock' type, i.e. it comprises only two blocks, one being soluble in the medium, the other being insoluble therein; it may, however, be of the 'triblock' type, and in this case, the sequence of the soluble and insoluble blocks is preferably alternating.
  • the copolymer is linear; it may, however, be branched and/or grafted.
  • the copolymer is not crosslinked; this is intended to mean that there is no intentional addition of compounds of which the purpose is to crosslink (crosslinking agent).
  • soluble is intended to mean that the block is completely dissolved (without apparent deposit, nor insoluble agglomerate or sediment), visually, at 20°C, at a concentration of greater than or equal to 5% by weight, in the medium under consideration.
  • the copolymers preferably have a number-average molecular weight (Mn) of between 1000 and 700 000, in particular between 10 000 and 500 000, and even better still between 15 000 and 350 000, or else between 25 000 and 150 000.
  • Mn number-average molecular weight
  • the copolymer has a polydispersity index by weight (PI) of less than or equal to 6, preferably between 1 .05 and 4, in particular between 1 .1 and 3, or even between 1 .15 and 2.5.
  • the copolymer according to the invention therefore comprises a first block that is soluble in the organic medium and at least one second block, that is insoluble in said medium.
  • the soluble block preferably comprises 50% to 100% by weight of monomer(s) that is (are) soluble in said medium, in particular from 60% to 90% by weight, and even better still from 70% to 80% by weight, of soluble monomer(s), alone or as a mixture. It may, however, also comprise 0 to 50% by weight, in particular from 10% to 40% by weight, or even from 20% to 30% by weight of monomer(s) that is (are) insoluble in said medium, alone or as a mixture.
  • the insoluble block preferably comprises 50% to 100% by weight of monomer(s) that is (are) insoluble in said medium, in particular from 60% to 90% by weight, and even better still from 70% to 80% by weight, of insoluble monomer(s), alone or as a mixture. It may, however, also comprise 0 to 50% by weight, in particular from 10% to 40% by weight, or even from 20% to 30% by weight of monomer(s) that is (are) soluble in said medium, alone or as a mixture.
  • the term "monomer that is soluble in the medium” is intended to mean any monomer of which the homopolymer is in soluble form, i.e. completely dissolved at a concentration of greater than or equal to 5% by weight at ambient temperature (20°C) in said medium.
  • insoluble monomer is therefore intended to mean any monomer of which the homopolymer is not in soluble form, i.e. completely dissolved at a concentration of greater than or equal to 5% by weight at ambient temperature (20°C) in said medium.
  • the insoluble monomers may, as monomers, be soluble in the medium under consideration, it being understood that they become insoluble after polymerization.
  • the proportion of soluble block and of insoluble block in the copolymer should be such that the copolymer can form a polymeric micelle.
  • the insoluble block (or the insoluble blocks) represents 30% to 97% by weight of the total weight of the copolymer, in particular from 40% to 95% by weight, or even from 50% to 93% by weight, in particular 60% to 92% by weight, and even better still from 75% to 90% by weight.
  • the soluble block (or the soluble blocks) therefore preferably represents 3% to 70% by weight of the total weight of the copolymer, in particular from 5% to 60% by weight, or even from 7% to 50% by weight, in particular from 8% to 40% by weight, and even better still from 10% to 25% by weight.
  • soluble monomer that can be used, mention may be made, alone or as a mixture, of the following monomers:
  • Ri represents a linear or branched C8-C22 alkyl group, such as lauryl, behenyl or stearyl; or else a cyclic alkyl group containing 8 to 30 carbon atoms, such as isobornyl; or else Ri represents the tert-butyl group;
  • R 2 represents a linear or branched C8-C22 alkyl group, such as lauryl, behenyl, stearyl or 2-ethylhexyl; or else a cyclic alkyl group containing 8 to 30 carbon atoms, such as isobornyl; or else R2 represents an isobutyl group;
  • R 5 represents a linear or branched C 3 to C12 alkyl group
  • R6O-CH CH 2 in which R 6 represents a linear or branched alkyl group containing from 8 to 22 carbon atoms.
  • R 2 represents a linear or branched C8-C22 alkyl group, such as lauryl, behenyl, 2-ethylhexyl or stearyl; or else a cyclic alkyl group containing 8 to 30 carbon atoms, such as isobornyl; or else R2 represents an isobutyl group.
  • insoluble monomers that may be used, mention may be made of, alone or as a mixture, the following monomers, and also the salts thereof and the mixtures thereof:
  • - a linear or branched alkyl group containing from 1 to 6 carbon atoms, it being possible for said group to comprise in each chain one or more heteroatoms chosen from O, N and S; and/or it being possible for said group to comprise one or more substituents chosen from -OH, halogen atoms and -NR'R" with R' and R", which may be identical or different, chosen from linear or branched Ci-C 4 alkyls; and/or it being possible for said group to be substituted with at least one polyoxyalkylene group, in particular with a C2-C 4 alkylene, especially a polyoxyethylene and/or a polyoxypropylene, said polyoxyalkylene group being constituted of a repetition of from 5 to 30 oxyalkylene units; tert-butyl methacrylate and isobutyl acrylate are excluded from this definition;
  • cyclic alkyl group containing from 3 to 6 carbon atoms, it being possible for said group to comprise in its chain one or more heteroatoms chosen from O, N and S, and/or it being possible for said group to comprise one or more substituents chosen from OH and halogen atoms (F, CI, Br, I);
  • R'i By way of examples of R'i, mention may be made of the methyl, ethyl, propyl, butyl, methoxyethyl, ethoxyethyl, methoxypolyoxyethylene 30, trifluoroethyl, 2-hydroxyethyl, 2-hydroxypropyl, dimethylaminoethyl, diethylaminoethyl and dimethylaminopropyl groups;
  • R' 3 and R' 4 which may be identical or different, represent a hydrogen atom or a linear or branched alkyl group containing from 1 to 6 carbon atoms, possibly comprising one or more substituents chosen from -OH, halogen atoms (F, CI, Br, I) and -NR'R" with R' and R", which may be identical or different, chosen from linear or branched Ci-C 4 alkyls; or - R'3 represents a hydrogen atom and R' 4 represents a 1 ,1 -dimethyl-3-oxobutyl group;
  • alkyl groups that can constitute R'3 and R' 4 , mention may be made of n-butyl, t-butyl, n-propyl, dimethylaminoethyl, diethylaminoethyl and dimethylaminopropyl;
  • -(iii) monomers comprising one or more ethylenic unsaturation(s) and comprising at least one carboxylic, phosphoric or sulphonic acid function, such as crotonic acid, maleic anhydride, itaconic acid, fumaric acid, maleic acid, styrenesulphonic acid, vinylbenzoic acid, vinylphosphoric acid, acrylic acid, methacrylic acid, acrylamidopropanesulphonic acid, and salts thereof;
  • carboxylic, phosphoric or sulphonic acid function such as crotonic acid, maleic anhydride, itaconic acid, fumaric acid, maleic acid, styrenesulphonic acid, vinylbenzoic acid, vinylphosphoric acid, acrylic acid, methacrylic acid, acrylamidopropanesulphonic acid, and salts thereof;
  • R'6-COO-CH CH 2 in which R'6 represents a linear or branched alkyl group containing from 1 to 6 atoms, or a cyclic alkyl group containing from 3 to 6 carbon atoms and/or an aromatic group, for example of benzene, anthracene or naphthalene type;
  • -(v) monomers comprising one or more ethylenic unsaturation(s) and comprising at least one tertiary amine function, such as 2-vinylpyridine, 4-vinylpyridine, and mixtures thereof;
  • ester group contains silanes, silsesquioxanes, siloxanes or carbosiloxane dendrimers as described in patent EP 0 963 751 , with the exception of monomers containing only one silicon atom, such as methacryloxypropyltrimethoxysilane.
  • Preferred monomers are (meth)acryloxypropyltris(trimethylsiloxy)silane, (meth)acryloxypropylbis(trimethyl- siloxy)methylsilane, (meth)acryloxymethyltris(trimethylsiloxy)silane and (meth)acryloxymethylbis(trimethylsiloxy)methylsilane;
  • - Rs denotes a hydrogen atom or a methyl group; preferably methyl
  • - R9 denotes a linear or branched, preferably linear, divalent hydrocarbon-based group containing from 1 to 10 carbon atoms and optionally containing one or two ether bonds -O-; preferably ethylene, propylene or butylene;
  • R10 denotes a linear or branched alkyl group containing from 1 to 10 carbon atoms, in particular from 2 to 8 carbon atoms; preferably methyl, ethyl, propyl, butyl or pentyl;
  • - n denotes an integer ranging from 1 to 300, preferably ranging from 3 to 200, and preferentially ranging from 5 to 100.
  • Monomethacryloyloxypropyl polydimethylsiloxanes such as those sold under the name PS560-K6 by UCT or under the name MCR-M17 by Gelest Inc. may in particular be used.
  • insoluble monomer that is particularly preferred, mention may be made of:
  • - Rs denotes a hydrogen atom or a methyl group; preferably methyl
  • - Rg denotes a linear or branched, preferably linear, divalent hydrocarbon-based group containing from 1 to 10 carbon atoms and optionally containing one or two ether bonds -O-; preferably ethylene, propylene or butylene;
  • - Rio denotes a linear or branched alkyl group containing from 1 to 10 carbon atoms, in particular from 2 to 8 carbon atoms; preferably methyl, ethyl, propyl, butyl or pentyl;
  • - n denotes an integer ranging from 1 to 300, preferably ranging from 3 to 200, and preferentially ranging from 5 to 100.
  • methyl (meth)acrylate ethyl (meth)acrylate, (meth)acrylic acid, maleic anhydride, (meth)acryloxypropyltris- (trimethylsiloxy)silane, (meth)acryloxypropylbis(trimethylsiloxy)methylsilane, (meth)acryloxymethyltris(trimethylsiloxy)silane and (meth)acryloxymethylbis- (trimethylsiloxy)methylsilane.
  • the polymers that are particularly preferred are the following polymers:
  • the polymers thus described can form a dispersion of particles in an organic medium; these dispersions can in particular be in the form of polymeric micelles (or particles) in a stable dispersion in the medium under consideration.
  • These micelles (or particles) preferably have a size of between 5 and 1000 nm, preferably 10 to 500 nm, even better still 20 to 300 nm, or even from 30 to 200 nm, which makes it possible to obtain great stability of the dispersion over time.
  • polymeric micelles is intended to mean self-dispersing particles obtained by self-assembly of the copolymers as defined hereinafter.
  • the polymerization of the monomer(s) making up the first block, of initiator and/or of controlling agent results in a first block that is soluble in the medium under consideration.
  • the addition of the monomer(s) intended to make up the core of the particle results in the formation of the copolymer, generally block copolymer, of soluble/insoluble type, which copolymer will spontaneously become organized into a polymeric micelle, i.e. form a polymer particle self-dispersed in carbon-based medium.
  • Said organic dispersion medium preferably comprises at least 50% by weight, in particular from 50% to 100% by weight, for example from 60% to 99% by weight, alternatively from 65% to 95% by weight, or even from 70% to 90% by weight, relative to the total weight of the carbon-based medium, of carbon-based compound which is liquid at 25°C, and which has a global solubility parameter in the Hansen solubility space of less than or equal to 20 (MPa) 1 2 , or a mixture of such compounds.
  • liquid carbon-based compounds having a global solubility parameter in the Hansen solubility space of less than or equal to 20 (MPa) 1 2 mention may be made of liquid fatty substances, in particular oils, which can be chosen from natural or synthetic, carbon-based, hydrocarbon-based, optionally fluoro, optionally branched, oils, alone or as a mixture.
  • oils which can be chosen from natural or synthetic, carbon-based, hydrocarbon-based, optionally fluoro, optionally branched, oils, alone or as a mixture.
  • - plant oils formed by fatty acid esters of polyols in particular triglycerides, such as sunflower oil, sesame oil or rapeseed oil, macadamia oil, soya bean oil, sweet almond oil, beauty-leaf oil, palm oil, grapeseed oil, maize oil, arara oil, cottonseed oil, apricot oil, avocado oil, jojoba oil, olive oil or cereal germ oil;
  • triglycerides such as sunflower oil, sesame oil or rapeseed oil, macadamia oil, soya bean oil, sweet almond oil, beauty-leaf oil, palm oil, grapeseed oil, maize oil, arara oil, cottonseed oil, apricot oil, avocado oil, jojoba oil, olive oil or cereal germ oil;
  • esters of formula RCOOR' in which R represents a higher fatty acid residue containing from 7 to 19 carbon atoms and R' represents a hydrocarbon-based chain containing from 3 to 20 carbon atoms, such as palmitates, adipates, myristates and benzoates, in particular diisopropyl adipate and isopropyl myristate;
  • volatile or non-volatile, linear, branched and/or cyclic alkanes such as optionally volatile C5-C60 isoparaffins such as isododecane, Parleam (hydrogenated polyisobutene), isohexadecane, cyclohexane or 'Isopars'; or else liquid paraffins, liquid petroleum jelly or hydrogenated polyisobutylene;
  • aliphatic fatty monoalcohols containing 6 to 30 carbon atoms, the hydrocarbon- based chain not comprising any substitution groups, such as oleyl alcohol, decanol, dodecanol, octadecanol, octyldodecanol and linoleyl alcohol;
  • the organic medium may also comprise volatile or non-volatile silicone oils, alone or as a mixture.
  • non-volatile silicone oils mention may in particular be made of:
  • non-volatile polydialkylsiloxanes such as non-volatile polydimethylsiloxanes (PDMSs), optionally substituted with aliphatic and/or aromatic groups, optionally fluorinated, and/or comprising functional groups such as hydroxyl, thiol and/or amine groups; and in particular polysiloxanes modified with fatty acids (in particular of C8-C20), fatty alcohols (in particular of C8-C20) or polyoxyalkylenes (in particular polyoxyethylene and/or polyoxypropylene); aminopolysiloxanes; polysiloxanes comprising hydroxyl groups; fluorinated polysiloxanes comprising a fluoro group which is pendant or at the end of a silicone chain containing from 1 to 12 carbon atoms, all or some of the hydrogens of which are substituted with fluorine atoms;
  • PDMSs non-volatile polydimethylsiloxanes
  • polydimethylsiloxanes comprising alkyl, alkoxy or phenyl groups, which are pendant or at the end of a silicone chain, it being possible for these groups to contain from 2 to 24 carbon atoms;
  • phenyl silicones such as phenyl trimethicones, phenyl dimethicones, phenyltrimethylsiloxydiphenylsiloxanes, diphenyl dimethicones, diphenylmethyldiphenyltrisiloxanes; and also polymethylphenylsiloxanes, optionally substituted with aliphatic and/or aromatic groups, optionally fluorinated, and/or comprising functional groups such as hydroxyl, thiol and/or amine groups;
  • cyclic or linear silicone oils having 2 to 7 silicon atoms, and optionally comprising alkyl or alkoxy groups containing from 1 to 10 carbon atoms, such as cyclodimethylsiloxanes, cyclophenylmethylsiloxanes and linear dimethylsiloxanes, and in particular linear dodecamethylpentasiloxane (L5), octamethylcyclotetrasiloxane (D4), decamethylcyclopentasiloxane (D5), dodecamethylcyclohexasiloxane (D6), heptamethylhexyltrisiloxane, heptamethyloctyltrisiloxane, octamethyltrisiloxane, decamethyltetrasiloxane, and mixtures thereof.
  • the organic carbon-based medium comprises at least one carbon- based compound chosen from:
  • esters of formula RCOOR' in which R represents a higher fatty acid residue containing 7 to 19 carbon atoms and R' represents a hydrocarbon-based chain containing from 3 to 20 carbon atoms;
  • the carbon-based organic medium comprises at least isopropyl myristate, octyldodecanol, C5-C60 isoparaffins, isohexadecane, isononyl isononanoate.
  • the organic medium under consideration contains, however, at least one 4-carboxy-2-pyrrolidinone derivative of formula (I) as defined above.
  • This derivative alone or as a mixture, may be the only constituent of the organic medium in which the block polymer is dispersed; said medium may, however, also comprise a carbon-based compound as defined above.
  • said compound of formula (I) represents 1 % to 90% by weight, in particular 2% to 70% by weight, or even 5% to 50% by weight, of the organic medium in which said block polymer is dispersed, the rest being constituted of the carbon-based compound(s).
  • the compound of formula (I) can, when it is used with at least one carbon-based compound, act as codispersant for the block polymer. It is thus possible to finally obtain a nonaqueous dispersion comprising an organic medium which comprises at least one compound of formula (I) and particles consisting of at least one block polymer as defined above.
  • Such dispersions may in particular be prepared according to the methods described in applications EP1704854 and EP1690526.
  • the polymers that can be used in the context of the present invention may also be polycondensates, in particular polyesters, polyurethanes, polyureas, polyethers, polythioethers, polyamides, polysulphones, polyethersulphones, polyimides, polycarbonates, polysiloxanes, and copolymers thereof.
  • polyesters from diesters and polyols (diol, triol, tetraol) with elimination of the corresponding alcohol (most commonly methanol or ethanol). This is then described as transesterification polycondensation.
  • a variant for obtaining polyesters consists in polymerizing lactones (cyclic esters) by ring- opening/polycondensation. According to the composition of their backbone, the polyesters may be classified as:
  • polyesters mention may, for example, be made of polyglycolide or poly(glycolic acid) obtained by polycondensation of glycolic acid, poly(lactic acid), polycaprolactones obtained by ring-opening of caprolactones or else polyethylene adipate;
  • polyesters mention may, for example, be made of polyethylene terephthalate obtained by polycondensation of terephthalic acid and of ethylene glycol, polybutylene terephthalate obtained by polycondensation of terephthalic acid and of 2,3-butanediol, polytrimethylene terephthalate obtained by polycondensation of terephthalic acid and of 1 ,3-propanediol, or else polyethylene naphthalate obtained by polycondensation of ethylene glycol and of naphthalene- dicarboxylic acid; and also sulphopolyesters prepared from sulphoisophthalic acid, anhydride or diester;
  • the polyester family also comprises modified alkyd and alkyd resins.
  • Alkyd resins in fact constitute a particular class of polyesters since they are the product of the reaction of polyols and polycarboxylic acids, generally modified with saturated or unsaturated fatty acids, for instance oleic acid, or with generally unsaturated oils, soya bean oil or castor oil for example, which make it possible to modulate their properties. Mention may, for example, be made of glycerophthalic resins.
  • Polycarbonates which contain the carbonate function in the repeating unit and are prepared by polycondensation are generally related to the polyester family.
  • the simplest method of synthesis is a polycondensation reaction between the carboxylic acid, or derivative, and amine functions.
  • a variant consists of opening/polycondensation of lactams (cyclic amides). According to the composition of their backbone chain, the polyamides are classified as:
  • polyamide 6 produced from
  • polyamide 66 produced from hexamethylenediamine and adipic acid
  • polyamide 6/66 produced from caprolactam, hexamethylenediamine and adipic acid
  • polyamide 66/610 produced from hexamethylenediamine, adipic acid and sebacic acid
  • polyphthalamides (semi-aromatic): mention may, for example, be made of polyamide 6T obtained by polycondensation of hexamethylenediamine with terephthalic acid;
  • aromatic polyamides mention may, for example, be made of polyamides resulting from the polycondensation of para-phenylenediamine with terephthalic acid. Mention may also be made of:
  • amide-terminated polyamide resins such as the commercial resins Haimalate PAM, Risocast PAM66, Sylvaclear A 200V and 2614V, or ester-terminated polyamide resins such as the commercial resins Uniclear 100VG and C75V;
  • silicone polyamides which are preferably solid at ambient temperature (25°C) and atmospheric pressure (760 mmHg), among which the silicone polyamides as described in US 5 981 680, and in particular the product sold under the reference DC 2-8179 by Dow Corning.
  • Polyurethanes which contain the urethane (carbamate) function in the repeating unit and are prepared by polycondensation of a monomer containing at least 2 isocyanate functions with another monomer containing at least 2 alcohol functions. Mention may, for example, be made of the polyurethanes prepared from:
  • - diisocyanates chosen from toluene diisocyanate (TDI), in particular the mixture of the two isomers 2,4 and 2,6, hexamethylene diisocyanate (HMDI), isophorone diisocyanate (IPDI), 2,2'-diphenylmethylene diisocyanate (2,2'-MDI), 4,4'-diphenylmethylene diisocyanate (4,4'-MDI), 4,4'-dibenzyl diisocyanate (4,4'-DBDI), m-xylylene diisocyanate (m-XDI), naphthalene diisocyanate (NDI), lysine diisocyanate (LDI) or else methylenebis(4-cyclohexylisocyanate) (H 12 MDI); and
  • aliphatic, cycloaliphatic or araliphatic diols which are saturated or unsaturated, preferably those which contain from 2 to 40 carbon atoms, in particular 8 to 32 carbon atoms, preferably chosen from alkanediols;
  • aliphatic, cycloaliphatic or araliphatic diols comprising ether bridges with an interval ranging from 2 to 10 carbon atoms between two ether bridges or oxygen atoms;
  • diol polymers ( ⁇ , ⁇ -diOH) in particular with an Mw of between 300 and 50 000, or even between 400 and 10 000, even 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 or polydimethylsiloxanes containing OH end groups
  • diols defined above mention may in particular be made of ethylene glycol, 1 ,2-propanediol, 1 ,3-propanediol, ethylene glycol mono-(3-hydroxypropy
  • the polyimides are polymers of which the macromolecular backbone contains repeating units containing the imide chemical function.
  • routes of synthesis are possible for preparing polyimides. Among these methods, mention will, for example, be made of reaction between a dianhydride and a diamine or else reaction between a dianhydride and a diisocyanate, or alternatively the polycondensation of amino acids.
  • These polymers may be both homopolymers derived from aspartic acid or glutamic acid, and copolymers derived from aspartic acid and glutamic acid in any proportions, or copolymers derived from aspartic acid and/or glutamic acid and from other amino acids (for example up to 15% by weight, preferably less than 5% by weight, of other amino acids).
  • copolymerizable amino acids mention may be made of glycine, alanine, valine, leucine, isoleucine, phenylalanine, methionine, tryptophan, histidine, proline, lysine, arginine, serine, threonine, cysteine, etc.
  • Said polyimides may have a weight-average molecular weight (Mw) of about 2000 to 10 7 and generally of about 3500 to 60 000.
  • Said polyimides in particular the polyimides derived from aspartic acid or glutamic acid can be prepared in particular by thermocondensation of said amino acid(s) in a substantially anhydrous medium, as described in J.A.C.S, 80, 3361 (1958), J. Med. Chem. 16, 893 (1973), Polymer 23, 1237 (1982) or in patent US 3 052 655.
  • Polysiloxanes, or silicones are polymers of which the chains are formed from alternating sequences of oxygen and silicon atoms substituted with organic groups.
  • the polysiloxanes are generally in the form of oily liquids, pastes, fats, waxes, elastomers, gums or resins.
  • the silicone gums are in particular polydiorganosiloxanes having weight-average molecular weights of between 100 000 and 1 000 000; mention may more particularly be made of the following products:
  • the organopolysiloxane resins are generally crosslinked siloxane systems containing the units: R2S1O2/2, R3SiOi/2, RS1O3/2 and SiO 4 /2 in which R represents a C1-C6 hydrocarbon-based group or a phenyl.
  • R represents a C1-C6 hydrocarbon-based group or a phenyl.
  • R denotes a Ci-C 4 alkyl group, more particularly methyl, or a phenyl group.
  • the organomodified silicones are generally silicones as defined above and comprising in their structure one or more organofunctional groups attached by means of a hydrocarbon-based group.
  • organomodified silicones mention may be made of polyorganosiloxanes comprising:
  • polyethyleneoxy and/or polypropyleneoxy groups optionally comprising C6-C2 4 alkyl groups, such as the products called dimethicone copolyol sold by the company Dow Corning under the name DC-1248 or the oils Silwet® L 722, L 7500, L 77 and L 71 1 from the company Union Carbide and alkyl(C12) methicone copolyol sold by the company Dow Corning under the name Q2-5200;
  • substituted or unsubstituted amine groups such as the products sold under the name GP 4 Silicone Fluid and GP 7100 by the company Genesee, or the products sold under the names Q2 8220 and Dow Corning 929 or 939 by the company Dow Corning.
  • the substituted amine groups are in particular Ci-C 4 aminoalkyl groups;
  • hydroxylated groups such as the polyorganosiloxanes comprising a hydroxyalkyl function that are described in French patent application FR-A-85 16334; - acyloxyalkyl groups such as, for example, the polyorganosiloxanes described in patent US-A-4957732;
  • a polyether is a polymer of which the macromolecular backbone contains repeating units containing the ether chemical function. Mention may, for example, be made of polyethylene glycol (PEG), polyethylene oxide, polypropylene glycol (PPG), polypropylene oxide (PPO), polytetramethylene glycol or poly(tetramethylene ether) glycol or else polytetrahydrofuran.
  • polyether- polyurethanes and in particular hydrophobically-modified nonionic polyether- polyurethanes, such as those described in applications EP861065, EP875237 and WO 99/36047, and more particularly the products sold by the company Rohm & Haas under the trade names Aculyn 46 and Aculyn 44;
  • a polysulphone is a polymer of which the macromolecular backbone contains repeating units containing the sulphone chemical function.
  • Polyethersulphones are most generally prepared by reacting a diphenol, for instance bisphenol-A, with a halophenylsulphone such as, for example, bis(4-chlorophenyl)sulphone.
  • the polymer that can be used is a polycondensate that can be obtained by reacting:
  • polycarboxylic acid comprising at least 2 carboxylic groups COOH, in particular 2 to 4 COOH groups; and/or a cyclic anhydride of such a polycarboxylic acid.
  • the polymer that can be used is a polycondensate that can be obtained by reacting:
  • polycarboxylic acid comprising at least 2 carboxylic groups COOH, in particular 2 to 4 COOH groups; and/or a cyclic anhydride of such a polycarboxylic acid.
  • the polymer that can be used is a polycondensate that can be obtained by reacting:
  • polycarboxylic acid comprising at least 2 carboxylic groups COOH, in particular 2 to 4 COOH groups; and/or a cyclic anhydride of such a polycarboxylic acid.
  • Said polyol may in particular be a linear, branched and/or cyclic, saturated or unsaturated, carbon-based, in particular hydrocarbon-based, compound containing 3 to 18 carbon atoms, in particular 3 to 12, or even 4 to 10 carbon atoms, and 3 to 6, in particular 3 to 4, hydroxyl (OH) groups, and possibly also comprising one or more oxygen atoms inserted in the chain (ether function).
  • Said polyol is preferably a linear or branched, saturated hydrocarbon-based compound containing 3 to 18 carbon atoms, in particular 3 to 12, or even 4 to 10 carbon atoms, and 3 to 6 hydroxyl (OH) groups.
  • triols such as 1 ,2,4-butanetriol, 1 ,2,6-hexanetriol, trimethylolethane, trimethylol- propane or glycerol;
  • tetraols such as pentaerythritol (tetramethylolmethane), erythritol, diglycerol or ditrimethylolpropane;
  • - hexols such as sorbitol and mannitol; or else dipentaerythritol or triglycerol.
  • the polyol is chosen from glycerol, pentaerythritol, diglycerol and sorbitol, and mixtures thereof; and even better still it is pentaerythritol.
  • the polyol, or the polyol mixture preferably represents 10% to 30% by weight, in particular 12% to 25% by weight, and better still 14% to 22% by weight, relative to the total weight of the final polycondensate.
  • Another constituent that is necessary for preparing the polycondensates according to the invention is a linear, branched and/or cyclic, saturated or unsaturated, nonaromatic monocarboxyhc acid containing 6 to 32 carbon atoms, in particular 8 to 28 carbon atoms and even better still 10 to 24, or even 12 to 20, carbon atoms.
  • a mixture of such nonaromatic monocarboxylic acids can obviously be used.
  • nonaromatic monocarboxylic acid is intended to mean a compound of formula RCOOH, in which R is a linear, branched and/or cyclic, saturated or unsaturated, hydrocarbon-based radical containing 5 to 31 carbon atoms, in particular 7 to 27 carbon atoms, and even better still 9 to 23 carbon atoms, or even 1 1 to 19 carbon atoms.
  • R is saturated.
  • said R radical is linear or branched, and preferentially of C5-C31 , or even C11 -C21 .
  • nonaromatic monocarboxylic acids that can be used, mention may be made of, alone or as a mixture:
  • - saturated monocarboxylic acids such as caproic acid, caprylic acid, isoheptanoic acid, 4-ethylpentanoic acid, 2-ethylhexanoic acid, 4,5-dimethylhexanoic acid, 2-heptylheptanoic acid, 3,5,5-trimethylhexanoic acid, octanoic acid, isooctanoic acid, nonanoic acid, decanoic acid, isononanoic acid, lauric acid, tridecanoic acid, myristic acid, palmitic acid, stearic acid, isostearic acid, arachidic acid, behenic acid, cerotic (hexacosanoic) acid; cyclopentanecarboxylic acid, cyclopentaneacetic acid, 3-cyclopentylpropionic acid, cyclohexanecarboxylic acid, cyclohexylacetic acid or 4-cyclohexyl
  • - unsaturated but nonaromatic monocarboxylic acids such as caproleic acid, obtusilic acid, undecylenic acid, dodecylenic acid, linderic acid, myristoleic acid, physeteric acid, tsuzuic acid, palmitoleic acid, oleic acid, petroselinic acid, vaccenic acid, elaidic acid, gondoic acid, gadoleic acid, erucic acid, cetoleic acid, nervonic acid, linoleic acid, linolenic acid or arachidonic acid.
  • caproleic acid such as caproleic acid, obtusilic acid, undecylenic acid, dodecylenic acid, linderic acid, myristoleic acid, physeteric acid, tsuzuic acid, palmitoleic acid, oleic acid, petroselinic acid, vaccenic acid, ela
  • Use may preferably be made of 2-ethylhexanoic acid, isooctanoic acid, lauric acid, myristic acid, isoheptanoic acid, isononanoic acid, nonanoic acid, palmitic acid, isostearic acid, stearic acid, behenic acid, and mixtures thereof, and even better still isostearic acid alone or stearic acid alone.
  • Said nonaromatic monocarboxylic acid, or the mixture of said acids preferably represents 10% to 70% by weight, in particular 15% to 65% by weight, or even 20% to 60% by weight, and better still 25% to 55% by weight, relative to the total weight of the final polycondensate.
  • Another constituent necessary for preparing the polycondensates according to the invention is an aromatic monocarboxylic acid containing 7 to 1 1 carbon atoms, also optionally substituted with 1 to 3 linear, branched and/or cyclic, saturated or unsaturated alkyl radicals which contain 1 to 32 carbon atoms, in particular 2 to 12, or even 3 to 8 carbon atoms.
  • aromatic monocarboxylic acid is intended to mean a compound of formula R'COOH, in which R' is an aromatic hydrocarbon-based radical containing 6 to 10 carbon atoms, and in particular benzoic and naphthoic radicals.
  • Said R' radical may also be substituted with 1 to 3 linear, branched and/or cyclic, saturated or unsaturated alkyl radicals containing 1 to 32 carbon atoms, in particular 2 to 12, or even 3 to 8 carbon atoms, and in particular chosen from methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, pentyl, isopentyl, neopentyl, cyclopentyl, hexyl, cyclohexyl, heptyl, isoheptyl, octyl or isooctyl.
  • Use may preferably be made of , benzoic acid, 4-tert-butyl benzoic acid, o-toluic acid, m-toluic acid and 1 -naphthoic acid, alone or as mixtures; and even better still benzoic acid alone.
  • Said aromatic monocarboxylic acid, or the mixture of said acids preferably represents 0.5% to 50% by weight, in particular 1 % to 40% by weight, even better still from 2% to 35% by weight, or even 2.5% to 8% by weight, relative to the total weight of the final polycondensate.
  • Another constituent necessary for preparing the polycondensates according to the invention is a linear, branched and/or cyclic, saturated or unsaturated, or even aromatic, polycarboxylic acid comprising at least 2 carboxylic groups COOH, in particular 2 to 4 COOH groups; and/or a cyclic anhydride of such a polycarboxylic acid.
  • a mixture of such polycarboxylic acids and/or anhydrides can obviously be used.
  • Said polycarboxylic acid may in particular be chosen from linear, branched and/or cyclic, saturated or unsaturated, or even aromatic, polycarboxylic acids containing 2 to 50, in particular 2 to 40, carbon atoms, in particular 3 to 36, or even 3 to 18, and even better still 4 to 12 carbon atoms, or even 4 to 10 carbon atoms; said acid comprises at least two carboxylic groups COOH, preferably from 2 to 4 COOH groups.
  • said polycarboxylic acid is a linear, saturated aliphatic polycarboxylic acid and contains 2 to 36 carbon atoms, in particular 3 to 18 carbon atoms, or even 4 to 12 carbon atoms; or else is aromatic and contains 8 to 12 carbon atoms. It preferably comprises 2 to 4 COOH groups.
  • polycarboxylic acids or anhydrides thereof that can be used, mention may be made of, alone or as a mixture:
  • dicarboxylic acids such as decanedioic acid, dodecanedioic acid, cyclopropane- dicarboxylic acid, cyclohexanedicarboxylic acid, cyclobutanedicarboxylic acid, naphthalene-1 ,4-dicarboxylic acid, naphthalene-2,3-dicarboxylic acid, naphthalene-2,6-dicarboxylic acid, suberic acid, oxalic acid, malonic acid, succinic acid, phthalic acid, terephthalic acid, isophthalic acid, tetrahydrophthalic acid, hexahydrophthalic acid, pimelic acid, sebacic acid, azelaic acid, glutaric acid, adipic acid, fumaric acid, maleic acid, itaconic acid, fatty acid dimers (in particular of C36) such as the products sold under the names Pripol 1006, 1009, 1013
  • - tricarboxylic acids such as cyclohexanetricarboxylic acid, trimellitic acid, 1 ,2,3- benzenetricarboxylic acid and 1 ,3,5-benzenetricarboxylic acid;
  • adipic acid, phthalic anhydride and/or isophthalic acid, and better still isophthalic acid alone, can be used.
  • Said polycarboxylic acid and/or cyclic anhydride thereof preferably represents 5% to 40% by weight, in particular 10% to 30% by weight, and better still 14% to 25% by weight, relative to the total weight of the final polycondensate.
  • the polycondensate that can be used is capable of being obtained by reacting:
  • At least one polyol chosen from, alone or as a mixture, 1 ,2,6-hexanetriol, trimethylolethane, trimethylolpropane, glycerol; pentaerythritol, erythritol, diglycerol, ditrimethylolpropane; xylitol, sorbitol, mannitol, dipentaerythritol and/or triglycerol; preferably present in an amount of from 10% to 30% by weight, in particular 12% to 25% by weight, and better still 14% to 22% by weight, relative to the total weight of the final polycondensate;
  • nonaromatic monocarboxylic acid chosen from, alone or as a mixture, caproic acid, caprylic acid, isoheptanoic acid, 4-ethylpentanoic acid, 2-ethylhexanoic acid, 4,5-dimethylhexanoic acid, 2-heptylheptanoic acid, 3,5,5- trimethylhexanoic acid, octanoic acid, isooctanoic acid, nonanoic acid, decanoic acid, isononanoic acid, lauric acid, tridecanoic acid, myristic acid, palmitic acid, stearic acid, isostearic acid, arachidic acid, behenic acid, cerotic (hexacosanoic) acid; cyclopentanecarboxylic acid, cyclopentaneacetic acid, 3-cyclopentylpropionic acid, cyclohexanecarboxylic acid, cyclohexanecar
  • aromatic monocarboxylic acid chosen from, alone or as a mixture, benzoic acid, o-toluic acid, m-toluic acid, p-toluic acid, 1 -naphthoic acid, 2-naphthoic acid, 4-tert-butyl benzoic acid, 1 -methyl-2-naphthoic acid, 2-isopropyl- 1 -naphthoic acid; preferably present in an amount from 0.1 % to 10% by weight, in particular 1 % to 9.5% by weight, or even 1 .5% to 8% by weight, relative to the total weight of the final polycondensate; and
  • polycarboxylic acid or an anhydride thereof, chosen from, alone or as a mixture, decanedioic acid, dodecanedioic acid, cydopropanedicarboxylic acid, cyclohexanedicarboxylic acid, cyclobutanedicarboxylic acid, naphthalene- 1 ,4-dicarboxylic acid, naphthalene-2,3-dicarboxylic acid, naphthalene-2,6- dicarboxylic acid, suberic acid, oxalic acid, malonic acid, succinic acid, phthalic acid, terephthalic acid, isophthalic acid, pimelic acid, sebacic acid, azelaic acid, glutaric acid, adipic acid, fumaric acid, maleic acid; cyclohexanetricarboxylic acid, trimellitic acid, 1 ,2,3-benzenetricarboxylic acid, 1
  • said polycondensate has a weight-average molecular weight (Mw) of between 1500 and 300 000, or even between 2000 and 200 000, and in particular between 3000 and 100 000.
  • Mw weight-average molecular weight
  • the polycondensate can be prepared by means of the polycondensation processes normally used by those skilled in the art.
  • a general preparation process is given in EP1870082.
  • polymers that can be used in the context of the present invention may also be polymers of natural origin, in their native or modified state. Mention may in particular be made of, alone or as mixtures:
  • polysaccharides which may be homopolysaccharides consisting of the same monosaccharide or heteropolysaccharides made up of various monosaccharides; mention may in particular be made of:
  • fructans or fructosans in particular inulin and graminan
  • - glucans in particular starch, carboxymethyl starch, pectin, amylopectin, amylose; cellulose and its alkyl, hydroxyalkyl, carboxyalkyl and/or nitrogenous derivatives, such as carboxymethylcellulose, hydroxypropylcellulose, hydroxypropyl methyl - cellulose, methylcellulose, nitrocellulose; curdlan, dextran, pullulan, chitin and chitosan;
  • polyesters which are obtained by polycondensation of monomers which are natural, or which are identical to the natural ones, for instance PLA (poly lactic acid) resulting from the polymerization of lactic acid molecules;
  • polyesters which are produced, by bacteria, from the fermentation of sugars and/or lipids, such as polyhydroxyalkanoates (or PHA); and more particularly PHB (polyhydroxybutyrate), PHV (polyhydroxyvalerate) and PHBV poly(3-hydroxybutyrate-co-3-hydroxyvalerate)).
  • the natural or modified-natural polymers that are preferred are in particular chosen from, alone or as a mixture:
  • chitosans such as chitosan succinamides
  • gums in particular gum arabic, guar gum, arabinogalactan gum, or hydroxypropyl guar; ethyl guar,
  • the polymers are preferably present, alone or as a mixture, in the cosmetic compositions according to the invention in an amount of from 2% to 99% by weight, better still from 3% to 90% by weight, or even 4% to 80% by weight, and preferentially from 5% to 70% by weight, even better still 6% to 65% by weight, or even 7% to 60% by weight, and even better still 8% to 50% by weight, relative to the total weight of the composition.
  • the compounds of formula (I) and the polymers are present in the cosmetic composition in a compound/polymer weight ratio of between 0.1/1 and 10/1 , in particular between 0.15/1 and 5/1 , better still between 0.2/1 and 3/1 , or even between 0.25/1 and 2.5/1 , and even better still between 0.3/1 and 1/1 .
  • the cosmetic compositions according to the invention also comprise a cosmetically acceptable medium, i.e. a medium that is compatible with keratin materials such as the skin of the face or the body, the lips, the hair, the eyelashes, the eyebrows and the nails.
  • a cosmetically acceptable medium i.e. a medium that is compatible with keratin materials such as the skin of the face or the body, the lips, the hair, the eyelashes, the eyebrows and the nails.
  • composition may advantageously comprise a fatty phase, which may itself comprise oils and/or solvents, which are preferably lipophilic, and also fatty substances that are solid at ambient temperature, such as waxes, pasty fatty substances, gums, and mixtures thereof.
  • a fatty phase which may itself comprise oils and/or solvents, which are preferably lipophilic, and also fatty substances that are solid at ambient temperature, such as waxes, pasty fatty substances, gums, and mixtures thereof.
  • volatile or non-volatile oils which may be chosen from natural or synthetic, carbon-based, hydrocarbon-based, fluoro, optionally branched, oils, alone or as a mixture.
  • non-volatile oil is intended to mean an oil capable of remaining on the skin for at least one hour at ambient temperature and atmospheric pressure and having in particular a non-zero vapour pressure at ambient temperature (25°C) and atmospheric pressure, of less than 0.01 mmHg (1 .33 Pa).
  • Mention may in particular be made of carbon-based, in particular hydrocarbon- based, non-volatile oils of plant, mineral, animal or synthetic origin, such as liquid paraffin (or liquid petroleum jelly), squalene, hydrogenated polyisobutene (Parleam), perhydrosqualene, mink oil, macadamia oil, turtle oil, soya bean oil, sweet almond oil, beauty-leaf oil, palm oil, grapeseed oil, sesame oil, maize oil, arara oil, rapeseed oil, sunflower oil, cottonseed oil, apricot oil, castor oil, avocado oil, jojoba oil, olive oil or cereal germ oil, shea butter oil; linear, branched or cyclic esters containing more than 6 carbon atoms, in particular 6 to 30 carbon atoms, such as esters of lanolic acid, of oleic acid, of lauric acid or of stearic acid; esters derived from acids or alcohols comprising a long chain (i.e.
  • esters of formula RCOOR' in which R represents a higher fatty acid residue containing from 7 to 19 carbon atoms and R' represents a hydrocarbon-based chain containing from 3 to 20 carbon atoms, in particular C12-C36 esters, such as isopropyl myristate, isopropyl palmitate, butyl stearate, hexyl laurate, diisopropyl adipate, isononyl isononanoate, 2-ethylhexyl palmitate, 2-hexyldecyl laurate, 2-octyl decyl palmitate, 2-octyldodecyl myristate, 2-octyldodecyl lactate, bis(2-ethylhexyl) succinate, diisostearyl malate, glyceryl triisostearate or diglyceryl triisostearate; higher fatty acids, in
  • decanol dodecanol, octadecanol, liquid triglycerides of fatty acids containing 4 to 10 carbon atoms, such as heptanoic or octanoic acid triglycerides, caprylic/capric acid triglycerides; linear or branched hydrocarbons of mineral or synthetic origin, such as paraffin oils and derivatives thereof, petroleum jelly, polydecenes, hydrogenated polyisobutene, such as Parleam; synthetic esters and ethers in particular of fatty acids, for instance Purcellin oil, isopropyl myristate, 2-ethylhexyl palmitate, 2-octyldodecyl stearate, 2-octyldodecyl erucate, isostearyl isostearate; hydroxylated esters, such as isostearyl lactate, octyl hydroxystearate, octy
  • ketones that are liquid at ambient temperature, such as methyl ethyl ketone, methyl isobutyl ketone, diisobutyl ketone, isophorone, cyclohexanone, acetone; propylene glycol ethers that are liquid at ambient temperature, 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 total), such as ethyl acetate, methyl acetate, propyl acetate, n-butyl acetate, isopentyl acetate; ethers that are liquid at ambient temperature, such as diethyl ether, dimethyl ether or dichlorodiethyl ether; alkanes that are liquid at ambient temperature, such as decane, heptane, dodecane, isododecane, is
  • non-silicone volatile oils in particular Cs-Ci6 isoparaffins such as isododecane, isodecane or isohexadecane. More preferentially, mention may be made of volatile or nonvolatile alkanes that are liquid at ambient temperature, and more particularly decane, heptane, dodecane, isododecane, isohexadecane, cyclohexane and isodecane, and mixtures thereof.
  • the fatty phase may be present in a content ranging from 0.01 % to 95%, preferably from 0.1 % to 90%, more preferably from 10% to 85% by weight, relative to the total weight of the composition, and better still from 30% to 80%.
  • the composition may also comprise a hydrophilic phase comprising water or a mixture of water and hydrophilic organic solvent(s) such as alcohols, and in particular linear or branched lower monoalcohols containing from 2 to 5 carbon atoms, such as ethanol, isopropanol or n-propanol, and polyols such as glycerol, diglycerol, propylene glycol, sorbitol, pentylene glycol and polyethylene glycols, or else C2 ethers and C2-C 4 aldehydes which are hydrophilic.
  • hydrophilic organic solvent(s) such as alcohols, and in particular linear or branched lower monoalcohols containing from 2 to 5 carbon atoms, such as ethanol, isopropanol or n-propanol, and polyols such as glycerol, diglycerol, propylene glycol, sorbitol, pentylene glycol and polyethylene glycols, or else C2 ether
  • the water or the mixture of water and hydrophilic organic solvents may be present in the composition according to the invention in a content ranging from 0.1 % to 80% by weight, relative to the total weight of the composition, and preferably from 1 % to 70% by weight.
  • the composition according to the invention may also comprise waxes and/or gums.
  • the term "wax” is intended to mean a lipophilic compound that is solid at ambient temperature (25°C), that has a reversible solid/liquid change of state, and that has a melting point of greater than or equal to 30°C which can range up to 120°C.
  • the melting point of the wax may be measured using a differential scanning calorimeter (DSC), for example the calorimeter sold under the name DSC 30 by the company Mettler.
  • DSC differential scanning calorimeter
  • 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 25°C and better still greater than 45°C.
  • wax that can be used in the composition of the invention mention may be made of beeswax, carnauba wax or candelilla wax, paraffin, microcrystalline waxes, ceresin or ozokerite; synthetic waxes such as polyethylene wax or Fischer- Tropsch wax, silicone waxes such as alkyl dimethicones or alkoxy dimethicones containing from 16 to 45 carbon atoms.
  • the gums are generally high-molecular-weight polydimethylsiloxanes (PDMSs) or cellulose gums or polysaccharides, and the pasty substances are generally hydrocarbon-based compounds, such as lanolins and derivatives thereof, or else PDMSs.
  • PDMSs polydimethylsiloxanes
  • hydrocarbon-based compounds such as lanolins and derivatives thereof, or else PDMSs.
  • the composition may contain from 0.01 % to 50% by weight of waxes, relative to the total weight of the composition, and better still from 1 % to 30% by weight.
  • the composition according to the invention may also comprise one or more dyestuffs chosen from water-soluble dyes, liposoluble dyes, and pulverulent dyestuffs such as pigments, nacres, and flakes well known to those skilled in the art.
  • the dyestuffs may be present, in the composition, in a content ranging from 0.01 % to 50% by weight, relative to the weight of the composition, preferably from 0.01 % to 30% by weight.
  • pigments should be understood as meaning white or coloured, mineral or organic particles of any form, 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 form, produced especially by certain molluscs in their shell, or else synthesized.
  • the pigments may be white or coloured, and mineral and/or organic.
  • the organic pigments include 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 coated with iron oxides, titanium mica coated with in particular Prussian blue or chromium oxide, titanium mica coated with an organic pigment of the abovementioned type and also nacreous pigments based on bismuth oxychloride.
  • water-soluble dyes mention may be made of the disodium salt of ponceau, the disodium salt of alizarin green, quinoline yellow, the trisodium salt of amaranth, the disodium salt of tartrazine, the monosodium salt of rhodamine, the disodium salt of fuchsin, xanthophyll and methylene blue.
  • the composition according to the invention may also comprise one or more fillers, in particular in a content ranging from 0.01 % to 50% by weight, relative to the total weight of the composition, preferably ranging from 0.01 % to 30% by weight.
  • fillers should be understood to mean colourless or white, mineral or synthetic particles of any form, which are insoluble in the medium of the composition irrespective of the temperature at which the composition is produced. These fillers serve in particular to modify the rheology or the texture of the composition.
  • the fillers may be mineral or organic of any form, platelet-shaped, spherical or oblong, irrespective of the crystallographic form (for example lamellar, cubic, hexagonal, orthorhombic, etc.).
  • talc Mention may be made of talc, mica, silica, kaolin, polyamide (Nylon®) powders (Orgasol® from Atochem), ⁇ - ⁇ -alanine powders and polyethylene powders, powders of tetrafluoroethylene polymers (Teflon®), lauroyllysine, starch, boron nitride, hollow polymer microspheres such as those of polyvinylidene chloride/acrylonitrile, for example 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 hydrogen carbonate, hydroxyapatite, hollow silica microspheres (Silica Beads® from Maprecos), glass or ceramic microcapsules, and metal soaps derived from organic carboxy
  • composition according to the invention may also comprise ingredients commonly used in the cosmetics industry, such as vitamins, thickeners, gelling agents, trace elements, softeners, sequestering agents, fragrances, basifying or acidifying agents, preservatives, sunscreens, surfactants, polymers, antioxidants, anti-hairloss agents, anti-dandruff agents, propellants, ceramides, or mixtures thereof. Needless to say, a person skilled in the art will take care to select this or these optional additional compound(s), and/or the amount thereof, such that the advantageous properties of the composition according to the invention are not, or are not substantially, adversely affected by the envisaged addition.
  • ingredients commonly used in the cosmetics industry such as vitamins, thickeners, gelling agents, trace elements, softeners, sequestering agents, fragrances, basifying or acidifying agents, preservatives, sunscreens, surfactants, polymers, antioxidants, anti-hairloss agents, anti-dandruff agents, propellants, ceramides, or mixtures thereof.
  • composition according to the invention may in particular be in the form of a suspension, a dispersion, a solution, in particular an organic solution, a gel, an emulsion, in particular an oil-in-water (O/W) or water-in-oil (W/O) emulsion, or a multiple emulsion (W/O/W or polyol/O/W or O/W/O), or in the form of a cream, a paste, a mousse, a dispersion of vesicles, in particular of ionic or nonionic lipids, a two-phase or multiphase lotion, a spray, a powder or a stick (wand).
  • a suspension in particular an organic solution, a gel
  • an emulsion in particular an oil-in-water (O/W) or water-in-oil (W/O) emulsion, or a multiple emulsion (W/O/W or polyol/O/W or O/W/O)
  • the composition according to the invention may be a makeup composition, in particular a complexion product such as a foundation, a face powder or an eye shadow; a lip product such as a lipstick, a lipcare product or a lip gloss; a concealer product; a blusher, a mascara, an eyeliner; an eyebrow makeup product, a lip pencil or an 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).
  • a complexion product such as a foundation, a face powder or an eye shadow
  • a lip product such as a lipstick, a lipcare product or a lip gloss
  • a concealer product such as a lipstick, a lipcare product or a lip gloss
  • a concealer product such as a lipstick, a lipcare product or a lip gloss
  • a concealer product such as a lipstick, a lipcare product or a lip gloss
  • a concealer product such as a lipstick, a lipcare product
  • the composition according to the invention may be a composition for protecting or caring for the skin of the face, the neck, the hands or the body, in particular an antiwrinkle composition, an antifatigue composition for making the skin look radiant, or a moisturizing or treating composition; an antisun or artificial tanning composition.
  • the composition according to the invention may also be a hair product, in particular for retaining the hairstyle or for shaping the hair; for caring for, conditioning or hygiene of the hair; or even for dyeing the hair.
  • the hair compositions are preferably shampoos, hair conditioners, hairsetting gels or lotions, blow-drying lotions, or fixing and styling compositions such as lacquers or sprays.
  • the lotions may be packaged in various forms, especially in vaporizers or pump-dispenser bottles, or in aerosol containers so as to allow application of the composition in vaporized form or in mousse form. Such packaging forms are indicated, for example, when it is desired to obtain a spray or a mousse for fixing or treating the hair.
  • a subject of the invention is also a cosmetic process for treating, in particular making up, cleansing, sun-protecting, shaping, dyeing or caring for keratin materials, in particular the skin of the body or the face, the lips, the nails, the hair and/or the eyelashes, comprising the application to said materials of a cosmetic composition as defined above.
  • Another subject of the invention is a compound which corresponds to one of the formulae hereinafter:
  • Yet another subject of the invention is a cosmetic composition
  • a cosmetic composition comprising, in a cosmetically acceptable medium, said compound, in particular in an amount of from 1 % to 30% by weight, or even 2% to 25% by weight, and preferentially from 3% to 20% by weight, relative to the total weight of the composition.
  • the temperature of the reaction medium is maintained at 90°C with regulation on the temperature of the reaction medium. Once the medium has become white, the following mixture is then introduced in 1 hour: 63 g of methyl acrylate and 0.99 g of Trigonox 21 S. The mixture is maintained at 90°C for 3 h and then the whole is cooled. The heptane is distilled-off and replaced during the distillation with 103.5 g of isododecane. A polymer containing 22% of active material, as a dispersion in isododecane, is obtained.
  • a coloured nail varnish having the following composition is prepared:
  • the varnish applies easily and forms a very glossy film which is very resistant to external attacks.
  • a lipgloss having the following composition is prepared:
  • the compound (l)/polymer ratio is 0.24/1 .
  • a lipstick having the following composition is prepared:
  • the compound (l)/polymer ratio is 0.27/1 .
  • a lipgloss having the following composition is prepared:
  • the compound (l)/polymer ratio is 0.43/1 .
  • a glossy film is obtained after application to the lips.
  • a lipstick having the following composition is prepared:
  • the compound (l)/polymer ratio is 0.5/1 .
  • a glossy coloured film is obtained after application to the lips.

Abstract

La présente invention concerne une composition cosmétique comprenant, dans un milieu cosmétiquement acceptable, de 2 % à 99 % en poids -par rapport au poids total de la composition - d'un polymère ou d'un mélange de polymères, et de 0,5 % à 40 % en poids d'un composé de formule (I), seul ou en tant que mélange, et/ou un sel de celui-ci :. Dans ladite formule, R1 représente H ou un radical alkyle C1-C20 linéaire ou C3-C20 ramifié; R2 représente un radical alkyle C1-C20 linéaire ou C3-C20 ramifié qui peut contenir un cycle C5-C6, un radical cycloalkyle C5-C6 éventuellement substitué, le radical phényle, le radical benzyle ou le radical phénéthyle; et R3 et R4 représentent H ou un radical alkyle C1-C12 linéaire ou C3-C12 ramifié. Il est entendu que lorsque R1 = H, les composés peuvent se trouver sous leur forme acide libre ou sous la forme de leurs sels cosmétiquement acceptables. L'invention porte en outre sur un procédé de traitement cosmétique utilisant ladite composition, ainsi que sur un composé spécifique.
PCT/EP2011/059630 2010-06-09 2011-06-09 Composition cosmétique comprenant un polymère et un dérivé de 4-carboxy-2-pyrrolidinone, composé et procédé de traitement cosmétique WO2011154508A1 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
FR1054519A FR2961093A1 (fr) 2010-06-09 2010-06-09 Composition cosmetique comprenant un polymere et un derive de 4-carboxy 2-pyrrolidinone, procede de traitement cosmetique et compose
FR1054519 2010-06-09
US35765410P 2010-06-23 2010-06-23
US61/357,654 2010-06-23

Publications (1)

Publication Number Publication Date
WO2011154508A1 true WO2011154508A1 (fr) 2011-12-15

Family

ID=43722607

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2011/059630 WO2011154508A1 (fr) 2010-06-09 2011-06-09 Composition cosmétique comprenant un polymère et un dérivé de 4-carboxy-2-pyrrolidinone, composé et procédé de traitement cosmétique

Country Status (2)

Country Link
FR (1) FR2961093A1 (fr)
WO (1) WO2011154508A1 (fr)

Cited By (24)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2984123A1 (fr) * 2011-12-19 2013-06-21 Oreal Composition cosmetique comprenant un derive d'acide imido-carboxylique sous forme solubilisee
WO2014037109A1 (fr) * 2012-09-07 2014-03-13 Clariant International Ltd Procédé de production d'esters de l'acide pyrrolidonecarboxylique n-substitués
WO2015148999A1 (fr) * 2014-03-27 2015-10-01 Inolex Investment Corporation Compositions de protection solaire pouvant être pulvérisées et procédés associés
US9717674B1 (en) 2016-04-06 2017-08-01 The Procter & Gamble Company Skin cleansing compositions comprising biodegradable abrasive particles
WO2020128050A1 (fr) 2018-12-20 2020-06-25 L'oreal Composition cosmétique comprenant un polyhydroxyalcanoate dans un milieu huileux
US10806692B2 (en) 2016-10-03 2020-10-20 The Procter & Gamble Company Skin cleansing compositions comprising color stable abrasive particles
CN112680187A (zh) * 2021-01-04 2021-04-20 上海晖研材料科技有限公司 一种表面改性的二氧化硅及含其的磨料组合物
FR3111557A1 (fr) 2020-06-23 2021-12-24 L'oreal Composition cosmétique comprenant un copolymère polyhydroxyalcanoate comprenant au moins deux unités polymériques différentes à chaine hydrocarbonée (in)saturée dans un milieu gras
WO2021260078A1 (fr) 2020-06-24 2021-12-30 L'oreal Composition cosmétique comprenant un copolymère de polyhydroxyalcanoate portant une chaîne hydrocarbonée (in)saturée et un tensioactif
WO2021260079A1 (fr) 2020-06-24 2021-12-30 L'oreal Composition cosmétique comprenant un copolymère de polyhydroxyalcanoate greffé dans un milieu gras
FR3130610A1 (fr) 2021-12-20 2023-06-23 L'oreal Composition comprenant un copolymère polyhydroxyalcanoate à longue chaine hydrocarbonnée à groupe(s) ionique(s), procédé de traitement des matières kératiniques mettant en œuvre la composition
FR3130611A1 (fr) 2021-12-20 2023-06-23 L'oreal Copolymère polyhydroxyalcanoate à groupe acétoacétate, composition le contenant et son utilisation en cosmétique
WO2023118529A1 (fr) 2021-12-23 2023-06-29 L'oreal Composition cosmétique comprenant un copolymère de polyhydroxyalcanoate portant une chaîne hydrocarbonée (in)saturée et une résine naturelle
WO2023118528A1 (fr) 2021-12-23 2023-06-29 L'oreal Composition cosmétique comprenant un copolymère de polyhydroxyalcanoate portant une chaîne hydrocarbonée (in)saturée et un polysaccharide
WO2023118467A1 (fr) 2021-12-23 2023-06-29 L'oreal Composition cosmétique comprenant un copolymère de polyhydroxyalcanoate portant une chaîne hydrocarbonée (in)saturée et une substance grasse cristallisable
WO2023118481A1 (fr) 2021-12-23 2023-06-29 L'oreal Composition cosmétique comprenant un copolymère de polyhydroxyalcanoate portant une chaîne hydrocarbonée (in)saturée et un mélange d'huile volatile et d'huile non volatile
WO2023118523A1 (fr) 2021-12-23 2023-06-29 L'oreal Composition cosmétique comprenant un copolymère de polyhydroxyalcanoate portant une chaîne hydrocarbonée (in)saturée et un oligo/polyester
WO2023118524A1 (fr) 2021-12-23 2023-06-29 L'oreal Composition cosmétique comprenant un copolymère de polyhydroxyalcanoate portant une chaîne hydrocarbonée (in)saturée et un polysaccharide modifié
WO2023118427A1 (fr) 2021-12-23 2023-06-29 L'oreal Composition cosmétique comprenant un copolymère de polyhydroxyalcanoate portant une chaîne hydrocarbonée (in)saturée et une argile
WO2023118526A1 (fr) 2021-12-23 2023-06-29 L'oreal Composition cosmétique comprenant un copolymère de polyhydroxyalcanoate portant une chaîne hydrocarbonée (in)saturée et un polymère hydrocarboné
WO2023118530A1 (fr) 2021-12-23 2023-06-29 L'oreal Composition cosmétique comprenant un copolymère de polyhydroxyalcanoate portant une chaîne hydrocarbonée (in)saturée et un polymère de silicone
FR3131204A1 (fr) 2021-12-23 2023-06-30 L'oreal Composition cosmétique comprenant un copolymère polyhydroxyalcanoate à chaine hydrocarbonée (in)saturé, et un plastifiant
FR3131208A1 (fr) 2021-12-23 2023-06-30 L'oreal Composition cosmétique comprenant un copolymère polyhydroxyalcanoate à chaine hydrocarbonée (in)saturé, et au moins un latex de polyuréthane
CN116508758A (zh) * 2023-06-28 2023-08-01 山东弥美生物科技股份有限公司 一种普鲁兰多糖制剂及其制备方法与应用

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN112125831B (zh) * 2020-09-22 2022-07-22 陕西科技大学 一种四酰胺非离子表面活性剂及其合成方法
CN112142640B (zh) * 2020-09-22 2022-07-22 陕西科技大学 一种具有阴阳离子反转能力的Bola型表面活性剂及其制备方法
FR3124730A1 (fr) * 2021-07-02 2023-01-06 L V M H Recherche Composition cosmétique de maquillage

Citations (25)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US282658A (en) 1883-08-07 James v
US2757125A (en) * 1952-05-16 1956-07-31 Colgate Palmolive Co N-higher alkyl-4-carboxy-2-pyrrolidones and compositions therewith
US2811496A (en) 1955-06-21 1957-10-29 Pfizer & Co C Vinyl halide resins plasticized with 1-substituted-4-carboalkoxy-2-pyrrolidinone
US3052655A (en) 1958-08-01 1962-09-04 Sidney W Fox Thermal polymerization of amino acid mixtures containing aspartic acid or a thermal precursor of aspartic acid
US3136620A (en) 1961-12-18 1964-06-09 Du Pont Composition and method for regulating plant growth
FR2290199A1 (fr) 1974-11-06 1976-06-04 Hoechst Ag Pyrrolidones, leur procede de preparation et leurs applications
EP0069512A2 (fr) 1981-07-08 1983-01-12 Pfizer Inc. Sels d'acides 2-pyrrolidone-4-carboxylique N-substitués en tant qu'agents humectants
EP0186507A2 (fr) 1984-12-22 1986-07-02 Chisso Corporation Composés siloxane contenant un groupe carboxyle
EP0342834A2 (fr) 1988-05-17 1989-11-23 Dow Corning Limited Traitement de matériaux fibreux
US4957732A (en) 1988-12-29 1990-09-18 L'oreal Shaving composition for the skin based on polyorgano-siloxanes containing an acyloxyalkyl group and process for use
FR2696744A1 (fr) 1992-10-12 1994-04-15 Logeais Labor Jacques Dérivés de 2-pyrrolidone, leur procédé de préparation et leurs applications en thérapeutique.
EP0749747A1 (fr) 1995-06-21 1996-12-27 L'oreal Composition comprenant une dispersion de particules de polymères dans un milieu non aqueux
EP0861065A2 (fr) 1996-07-23 1998-09-02 L'oreal Composition de teinture d'oxydation pour fibres keratiniques comprenant un polymere amphiphile non-ionique
EP0875237A2 (fr) 1997-05-02 1998-11-04 Rohm And Haas Company Compositions de teinture des cheveux et procédé pour l'épaississement de ces compositions
WO1999036047A1 (fr) 1998-01-16 1999-07-22 Bristol-Myers Squibb Company Compositions de teinture capillaire a deux composantes, renfermant des polyether-polyurethanes et des agents conditionneurs
US5981680A (en) 1998-07-13 1999-11-09 Dow Corning Corporation Method of making siloxane-based polyamides
US6673841B2 (en) 2001-12-20 2004-01-06 Whan In Pharm. Co., Ltd. Alprostadil alkyl ester-containing composition for external application
EP1411069A2 (fr) 2002-09-26 2004-04-21 L'oreal Polymères séquencés et compositions cosmétiques contenant de tels polymères
EP1428844A2 (fr) 2002-12-12 2004-06-16 L'oreal Dispersions de polymères en milieu organique.
EP1428843A1 (fr) 2002-12-12 2004-06-16 L'oreal Dispersions de polymères en milieu siliconé et composition les comprenant
EP1690526A1 (fr) 2005-02-15 2006-08-16 L'oreal Composition cosmétique comprenant une dispersion de particules de polymères, dispersion de particules de polymères et procédé comsétique l'utilisant
EP1704854A1 (fr) 2005-02-04 2006-09-27 L'oreal Dispersion de particules de polyméres
EP1870082A2 (fr) 2006-06-22 2007-12-26 L'Oréal Composition cosmétique comprenant un polycondensat
WO2008001240A2 (fr) 2006-06-29 2008-01-03 Kimberly-Clark Worldwide, Inc. Administration transdermique d'oléocanthal pour le soulagement de l'inflammation
EP1882709A1 (fr) 2006-07-27 2008-01-30 L'Oréal Polymères séquencés, et leur procédé de préparation

Patent Citations (25)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US282658A (en) 1883-08-07 James v
US2757125A (en) * 1952-05-16 1956-07-31 Colgate Palmolive Co N-higher alkyl-4-carboxy-2-pyrrolidones and compositions therewith
US2811496A (en) 1955-06-21 1957-10-29 Pfizer & Co C Vinyl halide resins plasticized with 1-substituted-4-carboalkoxy-2-pyrrolidinone
US3052655A (en) 1958-08-01 1962-09-04 Sidney W Fox Thermal polymerization of amino acid mixtures containing aspartic acid or a thermal precursor of aspartic acid
US3136620A (en) 1961-12-18 1964-06-09 Du Pont Composition and method for regulating plant growth
FR2290199A1 (fr) 1974-11-06 1976-06-04 Hoechst Ag Pyrrolidones, leur procede de preparation et leurs applications
EP0069512A2 (fr) 1981-07-08 1983-01-12 Pfizer Inc. Sels d'acides 2-pyrrolidone-4-carboxylique N-substitués en tant qu'agents humectants
EP0186507A2 (fr) 1984-12-22 1986-07-02 Chisso Corporation Composés siloxane contenant un groupe carboxyle
EP0342834A2 (fr) 1988-05-17 1989-11-23 Dow Corning Limited Traitement de matériaux fibreux
US4957732A (en) 1988-12-29 1990-09-18 L'oreal Shaving composition for the skin based on polyorgano-siloxanes containing an acyloxyalkyl group and process for use
FR2696744A1 (fr) 1992-10-12 1994-04-15 Logeais Labor Jacques Dérivés de 2-pyrrolidone, leur procédé de préparation et leurs applications en thérapeutique.
EP0749747A1 (fr) 1995-06-21 1996-12-27 L'oreal Composition comprenant une dispersion de particules de polymères dans un milieu non aqueux
EP0861065A2 (fr) 1996-07-23 1998-09-02 L'oreal Composition de teinture d'oxydation pour fibres keratiniques comprenant un polymere amphiphile non-ionique
EP0875237A2 (fr) 1997-05-02 1998-11-04 Rohm And Haas Company Compositions de teinture des cheveux et procédé pour l'épaississement de ces compositions
WO1999036047A1 (fr) 1998-01-16 1999-07-22 Bristol-Myers Squibb Company Compositions de teinture capillaire a deux composantes, renfermant des polyether-polyurethanes et des agents conditionneurs
US5981680A (en) 1998-07-13 1999-11-09 Dow Corning Corporation Method of making siloxane-based polyamides
US6673841B2 (en) 2001-12-20 2004-01-06 Whan In Pharm. Co., Ltd. Alprostadil alkyl ester-containing composition for external application
EP1411069A2 (fr) 2002-09-26 2004-04-21 L'oreal Polymères séquencés et compositions cosmétiques contenant de tels polymères
EP1428844A2 (fr) 2002-12-12 2004-06-16 L'oreal Dispersions de polymères en milieu organique.
EP1428843A1 (fr) 2002-12-12 2004-06-16 L'oreal Dispersions de polymères en milieu siliconé et composition les comprenant
EP1704854A1 (fr) 2005-02-04 2006-09-27 L'oreal Dispersion de particules de polyméres
EP1690526A1 (fr) 2005-02-15 2006-08-16 L'oreal Composition cosmétique comprenant une dispersion de particules de polymères, dispersion de particules de polymères et procédé comsétique l'utilisant
EP1870082A2 (fr) 2006-06-22 2007-12-26 L'Oréal Composition cosmétique comprenant un polycondensat
WO2008001240A2 (fr) 2006-06-29 2008-01-03 Kimberly-Clark Worldwide, Inc. Administration transdermique d'oléocanthal pour le soulagement de l'inflammation
EP1882709A1 (fr) 2006-07-27 2008-01-30 L'Oréal Polymères séquencés, et leur procédé de préparation

Non-Patent Citations (11)

* Cited by examiner, † Cited by third party
Title
DATABASE CA [Online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; 22 April 2001 (2001-04-22), KNUTH, CHARLES J. ET AL: "Plasticizer for polyvinyl resins-itaconic acid derivatives", XP002649209, retrieved from STN Database accession no. 1955:87836 *
GRULKE: "Polymer Handbook", article "Solubility parameter values", pages: 519 - 559
HANSEN: "The three dimensional solubility parameters", J. PAINT TECHNOL., vol. 39, 1967, pages 105
J. AM. CHEM. SOC., vol. 60, 1938, pages 402 - 6
J. INDUSTRIAL & ENGINEERING CHEM., vol. 47, 1955, pages 1572 - 8
J. MED. CHEM., vol. 16, 1973, pages 893
J. ORG. CHEM., vol. 26, 1961, pages 1519 - 24
J.A.C.S, vol. 80, 1958, pages 3361
POLYMER, vol. 23, 1982, pages 1237
SASAKI H ET AL: "Enhancing effect of pyrrolidone derivatives on transdermal drug delivery. I", INTERNATIONAL JOURNAL OF PHARMACEUTICS, ELSEVIER BV, NL, vol. 44, no. 1-3, 1 June 1988 (1988-06-01), pages 15 - 24, XP025554368, ISSN: 0378-5173, [retrieved on 19880601], DOI: DOI:10.1016/0378-5173(88)90095-6 *
TETRAHEDRON ASYMMETRIC, vol. 12, no. 23, 2001, pages 3241 - 9

Cited By (44)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2984123A1 (fr) * 2011-12-19 2013-06-21 Oreal Composition cosmetique comprenant un derive d'acide imido-carboxylique sous forme solubilisee
WO2014037109A1 (fr) * 2012-09-07 2014-03-13 Clariant International Ltd Procédé de production d'esters de l'acide pyrrolidonecarboxylique n-substitués
DE102012017739A1 (de) 2012-09-07 2014-03-13 Clariant International Ltd. Verfahren zur Herstellung von N-substituierten Pyrrolidoncarbonsäureestern
WO2015148999A1 (fr) * 2014-03-27 2015-10-01 Inolex Investment Corporation Compositions de protection solaire pouvant être pulvérisées et procédés associés
KR20160128417A (ko) * 2014-03-27 2016-11-07 인올렉스 인베스트먼트 코포레이션 분무식 선스크린 조성물들 및 방법들
KR102339775B1 (ko) 2014-03-27 2021-12-15 인올렉스 인베스트먼트 코포레이션 분무식 선스크린 조성물들 및 방법들
US9717674B1 (en) 2016-04-06 2017-08-01 The Procter & Gamble Company Skin cleansing compositions comprising biodegradable abrasive particles
US10806692B2 (en) 2016-10-03 2020-10-20 The Procter & Gamble Company Skin cleansing compositions comprising color stable abrasive particles
US11166905B2 (en) 2016-10-03 2021-11-09 The Procter & Gamble Company Skin cleansing compositions comprising color stable abrasive particles
FR3090365A1 (fr) 2018-12-20 2020-06-26 L'oreal Composition cosmétique comprenant un polyhydroxyalcanoate dans un milieu huileux
WO2020128050A1 (fr) 2018-12-20 2020-06-25 L'oreal Composition cosmétique comprenant un polyhydroxyalcanoate dans un milieu huileux
FR3111557A1 (fr) 2020-06-23 2021-12-24 L'oreal Composition cosmétique comprenant un copolymère polyhydroxyalcanoate comprenant au moins deux unités polymériques différentes à chaine hydrocarbonée (in)saturée dans un milieu gras
WO2021260048A1 (fr) 2020-06-23 2021-12-30 L'oreal Composition cosmétique comprenant un copolymère de polyhydroxyalcanoate comprenant au moins deux unités polymères différentes portant une chaîne hydrocarbonée (non) saturée dans un milieu gras
WO2021260078A1 (fr) 2020-06-24 2021-12-30 L'oreal Composition cosmétique comprenant un copolymère de polyhydroxyalcanoate portant une chaîne hydrocarbonée (in)saturée et un tensioactif
WO2021260079A1 (fr) 2020-06-24 2021-12-30 L'oreal Composition cosmétique comprenant un copolymère de polyhydroxyalcanoate greffé dans un milieu gras
FR3111811A1 (fr) 2020-06-24 2021-12-31 L'oreal Composition cosmétique comprenant un copolymère polyhydroxyalcanoate à chaine hydrocarbonée (in)saturé, et un tensioactif
FR3111812A1 (fr) 2020-06-24 2021-12-31 L'oreal Composition cosmétique comprenant un copolymère polyhydroxyalcanoate greffé dans un milieu gras
CN112680187A (zh) * 2021-01-04 2021-04-20 上海晖研材料科技有限公司 一种表面改性的二氧化硅及含其的磨料组合物
WO2023118007A1 (fr) 2021-12-20 2023-06-29 L'oreal Copolymère de polyhydroxyalcanoate portant un groupe acétoacétate, composition le contenant et son utilisation cosmétique
FR3130610A1 (fr) 2021-12-20 2023-06-23 L'oreal Composition comprenant un copolymère polyhydroxyalcanoate à longue chaine hydrocarbonnée à groupe(s) ionique(s), procédé de traitement des matières kératiniques mettant en œuvre la composition
FR3130611A1 (fr) 2021-12-20 2023-06-23 L'oreal Copolymère polyhydroxyalcanoate à groupe acétoacétate, composition le contenant et son utilisation en cosmétique
WO2023118230A2 (fr) 2021-12-20 2023-06-29 L'oreal Composition comprenant un copolymère de polyhydroxyalcanoate à chaîne longue à base d'hydrocarbures portant un ou plusieurs groupes ioniques, et procédé de traitement de matières kératiniques à l'aide de la composition
FR3131211A1 (fr) 2021-12-23 2023-06-30 L'oreal Composition cosmétique comprenant un copolymère polyhydroxyalcanoate à chaine hydrocarbonée (in)saturé, et une argile
FR3131209A1 (fr) 2021-12-23 2023-06-30 L'oreal Composition cosmétique comprenant un copolymère polyhydroxyalcanoate à chaine hydrocarbonée (in)saturé, et un polymère hydrocarboné
WO2023118481A1 (fr) 2021-12-23 2023-06-29 L'oreal Composition cosmétique comprenant un copolymère de polyhydroxyalcanoate portant une chaîne hydrocarbonée (in)saturée et un mélange d'huile volatile et d'huile non volatile
WO2023118523A1 (fr) 2021-12-23 2023-06-29 L'oreal Composition cosmétique comprenant un copolymère de polyhydroxyalcanoate portant une chaîne hydrocarbonée (in)saturée et un oligo/polyester
WO2023118524A1 (fr) 2021-12-23 2023-06-29 L'oreal Composition cosmétique comprenant un copolymère de polyhydroxyalcanoate portant une chaîne hydrocarbonée (in)saturée et un polysaccharide modifié
WO2023118427A1 (fr) 2021-12-23 2023-06-29 L'oreal Composition cosmétique comprenant un copolymère de polyhydroxyalcanoate portant une chaîne hydrocarbonée (in)saturée et une argile
WO2023118526A1 (fr) 2021-12-23 2023-06-29 L'oreal Composition cosmétique comprenant un copolymère de polyhydroxyalcanoate portant une chaîne hydrocarbonée (in)saturée et un polymère hydrocarboné
WO2023118530A1 (fr) 2021-12-23 2023-06-29 L'oreal Composition cosmétique comprenant un copolymère de polyhydroxyalcanoate portant une chaîne hydrocarbonée (in)saturée et un polymère de silicone
WO2023118528A1 (fr) 2021-12-23 2023-06-29 L'oreal Composition cosmétique comprenant un copolymère de polyhydroxyalcanoate portant une chaîne hydrocarbonée (in)saturée et un polysaccharide
WO2023118529A1 (fr) 2021-12-23 2023-06-29 L'oreal Composition cosmétique comprenant un copolymère de polyhydroxyalcanoate portant une chaîne hydrocarbonée (in)saturée et une résine naturelle
FR3131204A1 (fr) 2021-12-23 2023-06-30 L'oreal Composition cosmétique comprenant un copolymère polyhydroxyalcanoate à chaine hydrocarbonée (in)saturé, et un plastifiant
WO2023118467A1 (fr) 2021-12-23 2023-06-29 L'oreal Composition cosmétique comprenant un copolymère de polyhydroxyalcanoate portant une chaîne hydrocarbonée (in)saturée et une substance grasse cristallisable
FR3131210A1 (fr) 2021-12-23 2023-06-30 L'oreal Composition cosmétique comprenant un copolymère polyhydroxyalcanoate à chaine hydrocarbonée (in)saturé, et un mélange d’huile volatile et non volatile
FR3131202A1 (fr) 2021-12-23 2023-06-30 L'oreal Composition cosmétique comprenant un copolymère polyhydroxyalcanoate à chaine hydrocarbonée (in)saturé, et une résine naturelle
FR3131212A1 (fr) 2021-12-23 2023-06-30 L'oreal Composition cosmétique comprenant un copolymère polyhydroxyalcanoate à chaine hydrocarbonée (in)saturé, et un polysaccharide modifié
FR3131207A1 (fr) 2021-12-23 2023-06-30 L'oreal Composition cosmétique comprenant un copolymère polyhydroxyalcanoate à chaine hydrocarbonée (in)saturé, et un oligo/poly-ester
FR3131205A1 (fr) 2021-12-23 2023-06-30 L'oreal Composition cosmétique comprenant un copolymère polyhydroxyalcanoate à chaine hydrocarbonée (in)saturé, et un polymère siliconé
FR3131208A1 (fr) 2021-12-23 2023-06-30 L'oreal Composition cosmétique comprenant un copolymère polyhydroxyalcanoate à chaine hydrocarbonée (in)saturé, et au moins un latex de polyuréthane
FR3131203A1 (fr) 2021-12-23 2023-06-30 L'oreal Composition cosmétique comprenant un copolymère polyhydroxyalcanoate à chaine hydrocarbonée (in)saturé, et un polysaccharide
FR3131206A1 (fr) 2021-12-23 2023-06-30 L'oreal Composition cosmétique comprenant un copolymère polyhydroxyalcanoate à chaine hydrocarbonée (in)saturé, et un corps gras cristallisable
CN116508758A (zh) * 2023-06-28 2023-08-01 山东弥美生物科技股份有限公司 一种普鲁兰多糖制剂及其制备方法与应用
CN116508758B (zh) * 2023-06-28 2023-08-29 山东弥美生物科技股份有限公司 一种普鲁兰多糖制剂及其制备方法与应用

Also Published As

Publication number Publication date
FR2961093A1 (fr) 2011-12-16

Similar Documents

Publication Publication Date Title
WO2011154508A1 (fr) Composition cosmétique comprenant un polymère et un dérivé de 4-carboxy-2-pyrrolidinone, composé et procédé de traitement cosmétique
US7816464B2 (en) Polymer particle dispersion, cosmetic composition comprising it and cosmetic process using it
US10745582B2 (en) Dispersion of soft polymer particles, cosmetic composition comprising it and cosmetic treatment method
JP5037829B2 (ja) ポリマー粒子分散体を含む化粧品組成物、ポリマー粒子分散体、およびそれを使用する美容方法
KR101871661B1 (ko) 양이온성 (메타)아크릴 실리콘계 그라프트 공중합체 및 이를 함유하는 화장료
US20070104667A1 (en) Cosmetic composition comprising a cellulose or a liposoluble modified cellulose derivative
JP2006037109A (ja) 選択のモノマーを含む高級分枝状コポリマー、それを含む組成物、および化粧方法
JP2008501842A (ja) グラジエントコポリマー、それを含む組成物並びに美容メークアップ又は手入れ方法
ES2369172T3 (es) Polímero secuenciado, composición cosmética que lo contiene y procedimiento de tratamiento cosmético.
US9492369B2 (en) Emulsions containing saccharide siloxane copolymer emulsifiers and methods for their preparation and use
US9192564B2 (en) Saccharide siloxane copolymers and methods for their preparation and use
JP2008163313A (ja) 新規ブロックポリマー、それを含有する組成物及び処理方法
US20060193803A1 (en) Polymer particle dispersions, cosmetic compositions comprising at least one polymer particle dispersion, and cosmetic process using same
US20100284957A1 (en) Powder Treated with (Meth)Acrylic-Grafted Silicone Polymer and Product Using the Same
WO2006013200A1 (fr) Soins cosmétiques et/ou composition de maquillage comprenant au moins un polymère polyestérimide
US20060008431A1 (en) Copolymer functionalized with an iodine atom, compositions comprising the copolymer and treatment processes
JP2006225389A (ja) ポリマー粒子分散体を含む化粧品組成物、ポリマー粒子分散体およびこれを使用する美容方法
US20080181859A1 (en) Novel block (Co)polymers, compositions containing them, method of treatment and method of preparation
US20100021408A1 (en) Block polymer, cosmetic composition comprising it and cosmetic treatment process
JP2006002154A (ja) ヨウ素原子で官能化されたコポリマー、それを含む組成物およびトリートメント法
FR2931674A1 (fr) Composition cosmetique comprenant un polymere sequence et un polycondensat, et procede de traitement cosmetique
FR2937644A1 (fr) Dispersion de particules rigides de polymere, composition cosmetique la comprenant et procede de traitement cosmetique
US20070098664A1 (en) Cosmetic application of rod-coil copolymers
US20050288410A1 (en) Copolymer functionalized with an iodine atom, composition comprising it and treatment process
JP2006002155A (ja) ヨウ素原子により官能化されたコポリマー、それを含む組成物およびトリートメント方法

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 11724234

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 11724234

Country of ref document: EP

Kind code of ref document: A1