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EP1585777A2 - Cosmetic composition comprising a polymer - Google Patents

Cosmetic composition comprising a polymer

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Publication number
EP1585777A2
EP1585777A2 EP20030813184 EP03813184A EP1585777A2 EP 1585777 A2 EP1585777 A2 EP 1585777A2 EP 20030813184 EP20030813184 EP 20030813184 EP 03813184 A EP03813184 A EP 03813184A EP 1585777 A2 EP1585777 A2 EP 1585777A2
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EP
Grant status
Application
Patent type
Prior art keywords
composition
polymer
weight
according
liquid
Prior art date
Legal status (The legal status 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 status listed.)
Withdrawn
Application number
EP20030813184
Other languages
German (de)
French (fr)
Inventor
Pascal Arnaud
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
L'Oreal SA
Original Assignee
L'Oreal SA
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

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Classifications

    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES
    • A61K8/00Cosmetics or similar toilet preparations
    • A61K8/18Cosmetics or similar toilet preparations characterised by the composition
    • A61K8/30Cosmetics or similar toilet preparations characterised by the composition containing organic compounds
    • A61K8/58Cosmetics or similar toilet preparations characterised by the composition containing organic compounds containing atoms other than carbon, hydrogen, halogen, oxygen, nitrogen, sulfur or phosphorus
    • A61K8/585Organosilicon compounds
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES
    • A61K8/00Cosmetics or similar toilet preparations
    • A61K8/02Cosmetics or similar toilet preparations characterised by special physical form
    • A61K8/04Dispersions; Emulsions
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES
    • A61K8/00Cosmetics or similar toilet preparations
    • A61K8/18Cosmetics or similar toilet preparations characterised by the composition
    • A61K8/72Cosmetics or similar toilet preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84Cosmetics or similar toilet preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A61K8/89Polysiloxanes
    • A61K8/891Polysiloxanes saturated, e.g. dimethicone, phenyl trimethicone, C24-C28 methicone or stearyl dimethicone
    • A61K8/893Polysiloxanes saturated, e.g. dimethicone, phenyl trimethicone, C24-C28 methicone or stearyl dimethicone modified by an alkoxy or aryloxy group, e.g. behenoxy dimethicone or stearoxy dimethicone
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES
    • A61K8/00Cosmetics or similar toilet preparations
    • A61K8/18Cosmetics or similar toilet preparations characterised by the composition
    • A61K8/72Cosmetics or similar toilet preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/91Graft copolymers
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILET PREPARATIONS
    • A61Q1/00Make-up preparations; Body powders; Preparations for removing make-up
    • A61Q1/02Preparations containing skin colorants, e.g. pigments
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILET PREPARATIONS
    • A61Q1/00Make-up preparations; Body powders; Preparations for removing make-up
    • A61Q1/02Preparations containing skin colorants, e.g. pigments
    • A61Q1/04Preparations containing skin colorants, e.g. pigments for lips
    • A61Q1/06Lipsticks
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILET PREPARATIONS
    • A61Q1/00Make-up preparations; Body powders; Preparations for removing make-up
    • A61Q1/02Preparations containing skin colorants, e.g. pigments
    • A61Q1/08Preparations containing skin colorants, e.g. pigments for cheeks, e.g. rouge
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILET PREPARATIONS
    • A61Q1/00Make-up preparations; Body powders; Preparations for removing make-up
    • A61Q1/02Preparations containing skin colorants, e.g. pigments
    • A61Q1/10Preparations containing skin colorants, e.g. pigments for eyes, e.g. eyeliner, mascara
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILET PREPARATIONS
    • A61Q17/00Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
    • A61Q17/04Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILET PREPARATIONS
    • A61Q19/00Preparations for care of the skin
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILET PREPARATIONS
    • A61Q19/00Preparations for care of the skin
    • A61Q19/04Preparations for care of the skin for chemically tanning the skin
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F265/00Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F265/00Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00
    • C08F265/04Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00 on to polymers of esters
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F283/00Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
    • C08F283/06Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polyethers, polyoxymethylenes or polyacetals
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F290/00Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
    • C08F290/02Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
    • C08F290/04Polymers provided for in subclasses C08C or C08F
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F290/00Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
    • C08F290/02Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
    • C08F290/06Polymers provided for in subclass C08G
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F290/00Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
    • C08F290/02Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
    • C08F290/06Polymers provided for in subclass C08G
    • C08F290/068Polysiloxanes
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08LCOMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L51/00Compositions of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers
    • C08L51/003Compositions of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers grafted on to macromolecular compounds obtained by reactions only involving unsaturated carbon-to-carbon bonds
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08LCOMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L51/00Compositions of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers
    • C08L51/08Compositions of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers grafted on to macromolecular compounds obtained otherwise than by reactions only involving unsaturated carbon-to-carbon bonds

Abstract

The invention concerns a cosmetic make-up or skin care composition comprising particles of a grafted ethylene polymer dispersed in a liquid fatty phase, said composition being capable of forming a deposit having a transfer index less than 4 in the presence of sebum. The composition enables a deposit to be formed on the skin good transfer resistance, in particular in the presence of sebum.

Description

cosmetic composition comprising a polymer

The present invention relates to a cosmetic composition comprising a particular polymer to be applied to the skin of human beings.

The composition according to the invention may be a makeup composition or a skin care composition, preferably a makeup composition.

The makeup composition may be a foundation, an eyeshadow, a blusher, a concealer product, an eyeliner, a body makeup product. More specifically, the invention relates to a foundation composition.

The care composition can be a skin care product of the body and face, including a solar product, a skin coloring product (such as a self-tanning).

foundation compositions are commonly used to give an aesthetic color to the skin, particularly the face. These makeup products generally contain oils, pigments and / or fillers and optionally additives such as cosmetic or dermatological active.

These compositions, when applied to the skin, have the drawback of transferring, ie to deposit at least in part, leaving traces on certain substrates with which they can be contacted and in particular a glass, a cup, a cigarette, an item of clothing or the skin. It follows a poor holding of the applied film, requiring regular renewal application of the background composition of foundation or lipstick. Moreover, the appearance of these unacceptable traces, in particular on cols- may deviate from -chemisier--some-women-using -this deviation -de- makeup.

Furthermore, the sebum excreted by the skin over time also changes the properties of the makeup. In particular, the sebum does not promote the adhesion of makeup on the skin and transfer the makeup is even more important, resulting in a significant loss of makeup remaining on the skin.

therefore sought skin makeup compositions "transfer" which have the advantage of forming a resistant deposit transfer, especially in the presence of sebum, which in particular is not deposited, at least in part, on the media with which they come into contact (glass, clothing, cigarette or fabrics).

To improve the holding of makeup products, it is known to use film-forming polymers. For example, US-6074654 and WO02 / 067877 propose to use silicone resins.

The present invention therefore aims to provide a novel route for formulating a cosmetic product that allows to obtain good strength properties to the transfer, in particular in the presence of sebum.

The inventors have discovered that it is possible to obtain such a composition by using a particular polymer.

More specifically, the present invention therefore relates to a cosmetic composition for making up or caring for the skin comprising a dispersion of particles, preferably solid particles, of a grafted ethylenic polymer in a liquid fatty phase as described hereinafter , the composition being such as defined below.

Advantageously, the grafted ethylenic polymer is such that, when present in sufficient amount in the composition, the latter is capable of forming a deposit having-a-indiee for transfer présenee-sebum inferior to 4. -

The invention also relates to a skin makeup method comprising applying to the keratin materials, especially to the skin a composition as defined above. The invention also relates to the use of a composition as defined above to obtain a deposit, especially a make-up on the skin with good transfer resistance, especially in the presence of sebum.

The invention also relates to the use, in a cosmetic composition of a dispersion of particles (preferably solid) of a grafted ethylenic polymer dispersed in a liquid fatty phase, the composition being in particular capable of forming a deposit having a transfer index in the presence of less than 4 sebum, for obtaining a deposit, especially a make-up, on the skin with good transfer resistance, especially in the presence of sebum.

Advantageously, the grafted ethylenic polymer used in the composition according to the invention is such that when present in sufficient amount in the composition, the latter is capable of forming a deposit that has a transfer index in the presence of less sebum to 4, especially less than or equal to 3.5, preferably less than or equal to 3, especially less than or equal to 2.5, preferably less than or equal to 2, more preferably less than or equal to 1, 5, and especially less than or equal to 1.

The transfer index in the presence of sebum of the deposit obtained with the composition according to the invention is determined according to the measurement protocol described below.

A support (square of 40 mm × 40 mm) comprising a foam layer of neoprene adhesive on one of its faces (sold under the name RE70X40 212B from the company Joint Technique Lyonnais Ind). On the non-adhesive side of the support an adhesive ring is fixed with an -internal diameter -from -24 mm -and whose épaisseur- around -250- .mu.m - Θn -applique- inside the ring the composition which is leveled with a glass slide to obtain a deposit of the composition of about 250 .mu.m in thickness and then removed the crown and allowed to dry for 20 hours in an oven at 37 ° C. The carrier is then bonded via its adhesive face on a tip of a diameter of 27 mm attached to a press (STAND SV-1 MANUAL Imada Co. LTD) equipped with a dynamometer (DPS-5R from Imada Co. society LTD).

Lying on a photographic quality paper (EPSON S041061 reference 102g / m2), draw a strip 4 cm wide and 21 cm in length and in this band is drawn 5 squares each having a length of 4.2 cm according to the longitudinal axis of the strip. The paper is placed on the base of the press.

Is deposited in the center of the first box a drop of 10 .mu.l of artificial sebum having the following composition:

- 29% triolein

- 28.5% oleic acid

- oleyl oleate 18.5%

- Squalene 14%

- cholesterol 7%

- cholesterol palmitate 3%

Then press the medium (having the composition of sample) on the first space of the paper web to a force of approximately 4 kg exerted for 5 seconds. Then moves rectilinearly and regular paper over the entire length of the strip so that the support is in contact with the entire length of the strip. The travel of the web speed is of the order of 10 cm / s.

then observed visually trail of product deposited on the paper strip. Is assigned a score ranging OA 5 in increments of 0.5 based on the number of boxes of the first to the fifth vias in whole or part by the drag-potential-product.

For some products, not colored, a development step may be necessary so as to make visible the drag product. For example there is used a compound capable of producing a colored reaction product contact transferred. According to another example, is incorporated into the product to be tested an asset that emits in the visible at least a portion of UV radiation (Wood lamp).

The rating of 5 is given when, observation, after the relative movement between the paper and the support, it remains on the carrier substantially no product (less than 10%). In the latter case, the transfer may be described as total.

Note 5 is also allocated when the product trail extends beyond the fifth box, regardless of the amount of product remaining on the substrate.

A score of 0 is assigned if no product present on the support is transferred to the paper strip. No visible trace can be observed on the sheet. The transfer can be described as zero.

By convention, the separation line between the box and the box n + 1 is part of the box.

The table below illustrates how allocated to the other notes in function of the location on the boxes 1 to 5 wherein the product of the drag stop. In these notes, there is a greater or lesser amount of product on the support. The transfer is part.

The cosmetic composition according to the invention comprises a dispersion of particles, preferably solid particles, of a grafted ethylenic polymer in a liquid fatty phase.

The cosmetic composition according to the invention is a composition compatible with keratin materials, especially the skin.

The term "ethylenic polymer" means a polymer obtained by polymerizing monomers comprising an ethylenic unsaturation.

The dispersion of grafted ethylenic polymer is free of separate stabilizing polymer of said graft polymer, such as those described in EP749747, and the particles of grafted ethylenic polymer are therefore not surface-stabilized with such additional stabilizing polymers. The graft polymer is dispersed in ~ the liquid fatty phase in the absence of additional stabilizer surface of the particles of the graft polymer

By graft polymer means a polymer having a backbone comprising at least one pendant side chain or located at the chain end, and preferably pending.

Advantageously, the grafted ethylenic polymer comprises an ethylenic backbone insoluble in the said liquid fatty phase, and side chains covalently bound to said backbone and soluble in said dispersion medium.

The grafted ethylenic polymer is an uncrosslinked polymer. In particular, the polymer is obtained by polymerising monomers comprising one polymerizable group.

Preferably, the grafted ethylenic polymer is a film-forming polymer. Per polymer "film-forming" means a polymer capable, by itself or in the presence of an auxiliary film-forming agent, a continuous film that adheres to a support, especially to keratin materials.

According to one embodiment of the invention, the grafted ethylenic polymer is a grafted acrylic polymer.

The grafted ethylenic polymer is obtainable by radical polymerization in an organic polymerization medium:

- at least one ethylenic monomer, in particular of at least one acrylic monomer and optionally at least one non-acrylic vinyl monomer to form the said insoluble skeleton; and

- at least one macromonomer comprising a polymerizable end group to form the side chains, the said macromonomer having a weight average molecular weight greater than or equal to 200 and the content of polymerized macromonomer representing from 0.05 to 20% by weight of the polymer .

The liquid fatty phase may contain the organic polymerization medium.

The liquid organic dispersion medium corresponding to the medium is provided wherein the graft polymer may be the same to the polymerization medium. However, the polymerization medium can be substituted in whole or part with another liquid organic medium. This other liquid organic medium may be added after polymérisationj to the polymerization medium. This is then evaporated in whole or part.

The liquid fatty phase may contain liquid organic compounds other than those present in the dispersion medium. These other compounds are chosen so that the graft polymer remains in the state of dispersion in the liquid fatty phase.

The organic liquid dispersion medium is present in the liquid fatty phase of the composition according to the invention due to the introduction into the composition of the graft polymer dispersion obtained.

The liquid fatty phase preferably comprises predominantly one or more liquid organic compounds (or oils) as defined below. In particular, the liquid fatty phase is a non-aqueous liquid organic phase not miscible with water at room temperature (25 ° C).

The term "liquid organic compound" means a non-aqueous compound which is in liquid state at room temperature (25 ° C) and which therefore flows under its own weight.

The term "silicone compound" a compound containing at least one silicon atom.

Among the liquid organic compounds or oils, in particular volatile or non-volatile, which may be present in the liquid organic dispersion medium, there may be mentioned: - the liquid organic compounds, especially non-silicone or silicone-based, having a global solubility parameter according to the Hansen solubility space of less than or equal to 18 (MPa) 1 2, preferably less than or equal to 17 (MPa) 1/2, - the monoalcohols having an overall solubility parameter according to the Hansen solubility space of less than or equal to 20 (MPa) 1/2; and - mixtures thereof.

The overall solubility parameter δ according to the Hansen solubility space is defined in the article "Solubility parameter values" by Eric A.Grulke of the book "Polymer Handbook", 3rd edition, Chapter VII, p.519- 559 by the equation: δ = (d D 2 + d p 2 + d H 2) 1/2 wherein

- do characterizes the London dispersion forces resulting from the formation of dipoles induced during molecular impacts, - dp characterizes the forces of Debye interactions between permanent dipoles, and

- d H characterizes the forces of specific interactions (hydrogen bond, acid / base, donor / acceptor, etc.).

The definition of the solvents in the solubility space according to Hansen is described in the article by CM. Hansen "The three dimensional solubility parameters" J.Paint Technol. 39, 105 (1967).

Among the liquid organic compounds, especially non-silicone or silicone-based, having a global solubility parameter according to the Hansen solubility space or equal to 18 (MPa) 1/2, mention may be made of liquid fatty substances including oils, which may be selected from natural or synthetic oils, carbon, hydrocarbon, fluoro and silicone, optionally branched, alone or in admixture.

"Oil" means any non-aqueous medium liquid at room temperature (25 ° C) and atmospheric pressure (760 mmHg), compatible with application to the skin, mucous membranes (lips) and / or the skin appendages (nails, eyelashes, eyebrows, hair).

Among these -huiles include vegetable oils formed -by esters- of fatty acids and polyols, especially triglycerides, such as sunflower oil, sesame oil or rapeseed oil, or ester derivatives of long-chain acids or alcohols (that is to say those having from 6 to 20 carbon atoms), in particular esters of formula RCOOR 'wherein R represents the residue of a higher fatty acid containing from 7 to 19 carbon atoms and R 'represents a hydrocarbon chain having 3 to 20 carbon atoms, such as palmitates, adipates and benzoates, in particular diisopropyl adipate. Mention may also be linear alkanes, branched and / or cyclic volatile optionally including paraffin oils, petrolatum or hydrogenated polyisobutylene, isododecane or the "Isopars", volatile isoparaffins. Mention may also be esters, ethers, ketones. Mention may also be made of silicone oils such as polydimethylsiloxanes and polymethylphenylsiloxanes, optionally substituted with aliphatic and / or aromatic, optionally fluorinated, or with functional groups such as hydroxyl, thiol and / or amine, and silicone oils volatile, especially cyclic.

In particular, there may be mentioned silicone oils, optionally branched, volatile and / or nonvolatile.

Volatile oil, any non-aqueous medium capable of evaporating from the skin or the lips in less than one hour, especially having a vapor pressure at room temperature and atmospheric pressure ranging from 10 "3 to 300 mm Hg (0.13 Pa to 40 000 Pa).

As volatile silicone oils usable in the invention include linear or cyclic silicone having 2 to 7 silicon atoms, these silicones optionally comprising alkyl or alkoxy groups having 1 to 10 carbon atoms. In particular, include octamethylcyclotetrasiloxane, decamethylcyclopentasiloxane, dodecamethylcyclohexasiloxane, heptamethylhexyltrisiloxane, heptamethyloctyltrisiloxane, octamethyltrisiloxane, decamethyltetrasiloxane and mixtures thereof.

Non-volatile silicone oil include non -v0.ati.s polydialkylsiloxanes 7 - tels- -that --the polydimethylsiloxanes (-P-DMS) - non volatilsf -les- polydimethylsiloxanes comprising alkyl, alkoxy or phenyl groups, pendent or at the silicone chain, these groups containing from 2 to 24 carbon atoms; phenylated silicones such as phenyl trimethicones, phenyl dimethicones, phenyl trimethylsiloxy diphenylsiloxanes, diphenyl dimethicones, diphenylmethyldiphenyltrisiloxanes, polymethylphenylsiloxanes; polysiloxanes modified with fatty acids (in particular C 8 -C 20), fatty alcohols (in particular C 8 -C 20) or polyoxyalkylenes (especially polyoxyethylene and / or polyoxypropylene); aminated polysiloxanes; polysiloxanes containing hydroxyl groups; fluoro polysiloxanes comprising a fluoro group that is pendent or at the silicone chain having from 1 to 12 carbon atoms of which some or all of hydrogen are substituted by fluorine atoms; and mixtures thereof.

There may be mentioned in particular as non-silicone liquid organic compounds having an overall solubility parameter according to the Hansen solubility space of less than or equal to 18 (MPa) 1/2:

- linear esters, branched or cyclic, having at least 6 carbon atoms, especially 6 to 30 carbon atoms;

- ethers having at least 6 carbon atoms, especially 6 to 30 carbon atoms; and

- ketones having at least 6 carbon atoms, especially 6 to 30 carbon atoms.

Liquid monoalcohols having an overall solubility parameter according to the Hansen solubility space of less than or equal to 20 (MPa) 1/2, means aliphatic fatty liquid monoalcohols containing 6 to 30 carbon atoms, the hydrocarbon chain not comprising no substitution group. Monoalcohols according to the invention include oleyl alcohol, decanol and linoleyl alcohol.

Advantageously, the composition according to the invention may comprise a volatile oil in a content ranging from 1% to 90% by weight, based on the total weight of -the-composition-and-da.pr-éféπence-allant.de_5. . à_70% _% by weight. ___. ....

The composition may comprise a non-volatile oil in a content ranging from 0.1% to 80% by weight, based on the total weight of the composition, and preferably ranging from 3% to 50% by weight. According to a first embodiment of the invention, the liquid fatty phase may be a non-silicone liquid fatty phase.

The term "non-silicone liquid fatty phase" a fatty phase comprising one or more liquid organic compounds or non-silicone oils (s), such as those mentioned above, said non-silicone compounds being predominantly present in the liquid fatty phase, c ' is to say at least 50% by weight, especially from 50 to 100% by weight, preferably from 60% to 100% by weight (e.g. 60 to 99% by weight), or from 65% to 100% by weight (e.g. 65 to 95% by weight), relative to the total weight of the liquid fatty phase.

Non-silicone liquid organic compounds may especially be chosen from:

- non-silicone liquid organic compounds having an overall solubility parameter according to the Hansen solubility space of less than or equal to 18 (MPa) 1/2, monoalcohols having a global solubility parameter according to the space of n illuubbiilliittéé ooff HHaannssen less than or equal to 20 (MPa) 1/2; and mixtures thereof.

Said non-silicone liquid fatty phase may thus optionally comprise silicone oils or organic liquid compound (s), such as those mentioned above, which may be present in an amount less than 50% by weight, especially ranging from 0.1 to 40 % by weight, or even ranging from 1 to 35% by weight, or from 5 to 30% by weight, based on the total weight of the liquid fatty phase.

According to a particular embodiment of the invention, the non-silicone liquid fatty phase does not contain any silicone liquid organic compounds or oils (s).

-When-the liquid fatty phase is a non-silicone liquid fatty phase, -the macromonomers present in the grafted polymer are advantageously carbon-based macromonomers as described below.

When the liquid fatty phase is a non-silicone liquid fatty phase, the macromonomers present in the grafted polymer are advantageously carbon-based macromonomers as described below.

By non-silicone graft polymer means a grafted polymer predominantly containing a carbon-based macromonomer and optionally containing at most 7% by weight of the total polymer weight, preferably at most 5% by weight, or even being free of silicone macromonomer.

According to a second embodiment of the invention, the liquid fatty phase can be a silicone liquid fatty phase.

The term "silicone-based liquid fatty phase" a fatty phase comprising one or more liquid organic silicone compounds or silicone oils such as those described above, said silicone compounds being predominantly present in the liquid fatty phase, that is to say at least 50% by weight, especially from 50 to 100% by weight, preferably from 60% to 100% by weight (e.g. 60 to 99% by weight), or from 65% to 100% by weight (e.g. 65 to 95% by weight), relative to the total weight of the liquid fatty phase.

The silicone-based liquid organic compounds may especially be chosen from:

- liquid organic compounds, especially non-silicone or silicone-based, having a global solubility parameter according to the Hansen solubility space of less than or equal to 18 (MPa) 1/2.

Said silicone-based liquid fatty phase may thus optionally comprise liquid organic compounds or non-silicone oils (s), as described

-précédemment! which may be present in an amount inferior-to-50% -eh weight, especially ranging from 0.1 to 40% by weight or even from 1 to 35% by weight, or from 5 to 30% by weight, relative to the total weight of the liquid fatty phase da. According to a particular embodiment of the invention, the silicone-based liquid fatty phase does not contain organic compounds non-silicone liquid.

When the liquid fatty phase is a silicone liquid fatty phase, the macromonomers present in the grafted polymer are advantageously macromonomers when the liquid fatty phase is a silicone liquid fatty phase, the macromonomers present in the grafted polymer are advantageously silicone macromonomers as described below.

In particular, when the liquid fatty phase is a silicone liquid fatty phase, the grafted polymer present in the composition is advantageously a silicone graft polymer.

By polymer grafted silicone means a grafted polymer predominantly containing a silicone-based macromonomer and optionally containing at most 7% by weight of the total polymer weight, preferably at most 5% by weight, or even being free of carbon-based macromonomer, silicone such as described below.

The choice of monomers constituting the polymer backbone, macromonomers, the molecular weight of the polymer, the proportion of monomers and macromonomers may be made depending on the liquid organic dispersion medium so as to advantageously obtain a dispersion of grafted polymer particles particular a stable dispersion, this choice may be made by those skilled in the art.

By "stable dispersion" is meant a dispersion which is not liable to form a solid deposit or liquid phase / solid particular after - --centrifugation, for-example; -to 4000 revolutions / minute for 15 minutes,

The grafted ethylenic polymer forming the particles in dispersion thus comprises a skeleton that is insoluble in said dispersion medium and a portion soluble in said dispersion medium. The grafted ethylenic polymer may be a random polymer.

According to the invention, the term "grafted ethylenic polymer" means a polymer capable of being obtained by radical polymerization:

- one or more monomer (s) ethylenic (s),

- with one or more macromonomer (s), in an organic polymerization medium.

According to the invention, the term "grafted acrylic polymer" means a polymer capable of being obtained by radical polymerization:

- one or more monomer (s) acrylic acid (s), and optionally one or more monomer (s) Additional (s) vinyl (s) non-acrylic (s),

- with one or more macromonomer (s), in an organic polymerization medium.

Advantageously, the acrylic monomers represent from 50 to 100% by weight, preferably 55 to 100% by weight (in particular from 55 to 95% .in weight), preferably from 60 to 100% by weight (in particular from 60 to 90% by weight) mixture of acrylic monomers + optional non-acrylic vinyl monomers.

Preferably, the acrylic monomers are chosen from monomers whose homopolymer is insoluble in the dispersion medium under consideration, that is to say that the homopolymer is in solid form (or undissolved) at a concentration greater than or equal to 5% by weight at room temperature (20 ° C) in said dispersion medium.

According to-the invention, -on-means-by- "macr-omonomère having a polymerizable grαupe-terminal" any polymer comprising on one of its ends, a polymerizable end group capable of reacting during the polymerization reaction with the acrylic monomers and optionally the additional non-acrylic vinyl monomers constituting the skeleton. The macromonomer used to form the side chains of the grafted acrylic polymer. The polymerizable group of the macromonomer may preferably be an ethylenically unsaturated group capable of free radical polymerization with the monomers constituting the skeleton.

By "carbon-based macromonomer" means a non-silicone macromonomer, and in particular an oligomeric macromonomer obtained by polymerizing monomer (s) non-silicone (s) containing ethylenic unsaturation, and mainly by polymerization of acrylic monomers and / or non-acrylic vinyl monomers.

By "silicone macromonomer" means an organopolysiloxane macromonomer and in particular a polydimethylsiloxane macromonomer.

Preferably, the macromonomer is chosen from macromonomers whose homopolymer is soluble in the dispersion medium under consideration, that is to say completely dissolved at a concentration greater than or equal to 5% by weight and at room temperature in said medium dispersion.

Thus, the grafted acrylic polymer comprises a backbone (or main chain) consisting of a sequence of acrylic units resulting from the polymerization including one or more acrylic monomers and side chains (or grafts) derived from the reaction of the macromonomers, said chains side being covalently bonded to said main chain. The skeleton (or main chain) is insoluble in the dispersion medium under consideration, whereas the side chains (or grafts) are soluble in said dispersion medium.

By "acrylic monomer" is meant herein the monomers selected from (meth) acrylic acid, esters of (meth) acrylic acid (also appelés- les (meth) acrylates), amides of '(methacrylic acid) (also known as (meth) acrylamides).

As acrylic monomers which can be employed to form the insoluble skeleton of the polymer, mention may be made, alone or as a mixture, the following monomers and their salts:

- (i) (meth) acrylates of formula

CH, COOR 2

Ri wherein:

- R denotes a hydrogen atom or a methyl group;

- R 2 represents a group selected from:

- a linear or branched alkyl group comprising 1 to 6 carbon atoms, said group possibly comprising in its chain one or more heteroatoms selected from O, N and S; and / or possibly comprising one or more substituents selected from -OH, halogen atoms (F, Cl, Br, I) and - NR'R "with R 'and R" are identical or different, chosen from linear or branched alkyl C1-C4 alkyl; and / or may be substituted by at least one polyoxyalkylene group, in particular C 2 -C 4 alkylene, in particular polyoxyethylene and / or polyoxypropylene, said polyoxyalkylene group consisting of the repetition of 5 to 30 oxyalkylene units;

- a cyclic alkyl group having 3 to 6 carbon atoms, said group possibly comprising in its chain one or more heteroatoms selected from O, N and S, and / or possibly comprising one or more substituents selected from OH and atoms halogen (F, Cl, Br, I);

Examples of R 2 include methyl, ethyl, propyl, butyl, isobutyl, methoxyethyl, ethoxyethyl, methoxy polyoxyethylene-350 OE, trifluoroethyl, 2-hydroxyethyl, 2-hydroxypropyl, dimethylaminoethyl, diethylaminoethyl, dimethylaminopropyl.

- (ii) (meth) acrylamides of formula:

wherein: - R 3 denotes a hydrogen atom or a methyl group;

- R and R 5, identical or different, represent a hydrogen atom or an alkyl group, linear or branched, having 1 to 6 carbon atoms, possibly comprising one or more substituents selected from -OH, halogen atoms (F, Cl, Br, I) and -NR'R "with R 'and R" are identical or different, chosen from linear or branched Cι-C4 alkyls; or

- R represents a hydrogen atom and R 5 represents a 1, 1-dimethyl-3-oxobutyl group.

Examples of alkyl groups that may constitute R 4 and R 5, there may be mentioned n-butyl, t-butyl, n-propyl, dimethylaminoethyl, diethylaminoethyl, dimethylaminopropyl.

the (meth) acrylic monomers comprising at least one carboxylic, phosphoric or sulfonic acid, such as acrylic acid, methacrylic acid, acrylamidopropanesulphonic acid.

Among these acrylic monomers, mention may be made most particularly methyl (meth) acrylates, ethyl, propyl, butyl, isobutyl; (meth) acrylates, methoxyethyl or ethoxyethyl; trifluoroethyl methacrylate; dimethylaminoethyl methacrylate, diethylaminoethyl methacrylate, 2-hydroxypropyl methacrylate, 2-hydroxyethyl acrylate, 2-hydroxypropyl acrylate, 2-hydroxyethyl; dimethylaminopropylmethacrylamide, (meth) acrylic acid; and salts thereof; and mixtures thereof.

Preferably, the acrylic monomers are selected from methyl acrylate, methoxyethyl acrylate, methyl methacrylate, 2-hydroxyethyl methacrylate, (meth) acrylic acid, dimethylaminoethyl methacrylate, and mixtures thereof.

Among the non-acrylic vinyl monomers include: - vinyl esters of the formula: R 6 -COO-CH = CH 2 wherein RQ represents a linear or branched alkyl group comprising from 1 to 6 atoms, or an alkyl group cyclic having 3 to 6 carbon atoms and / or an aromatic group, for example of benzene, anthracene or naphthalene;

- non-acrylic vinyl monomers comprising at least one carboxylic acid functionality, phosphoric or sulfonic acid, such as crotonic acid, maleic anhydride, itaconic acid, fumaric acid, maleic acid, styrenesulfonic acid, vinylbenzoic acid, vinylphosphoric acid, and salts thereof;

- non-acrylic vinyl monomers comprising at least one tertiary amine function, such as 2-vinylpyridine, 4-vinylpyridine; - and mélangeas.

According to one embodiment of the invention, the graft polymer comprises (meth) acryiique.

Advantageously, the acrylic monomers present in the graft polymer comprise at least (meth) acrylic acid, and especially at least (meth) acrylic acid and at least one monomer chosen from (meth) acrylates and (meth) acrylamides described above in points (i) and (ii). Preferably, the acrylic monomers comprise at least (meth) acrylic acid and at least one monomer selected from alkyl (meth) acrylates C-1-C3. (Meth) acrylic acid may be present in a content of at least 5% by weight, based on the total weight of the polymer (especially ranging from 5% to 80% by weight), preferably at least 10% by weight (in particular from 10% by weight to 70% by weight), preferably at least 15% by weight (in particular from 15% to 60% by weight).

Among the salts that may be mentioned those obtained by neutralizing the acid groups with inorganic bases such as sodium hydroxide, potassiumH'hydroxyde-d ^ ammonium hydroxide or organic-type -bases aleanols- amines such as monoethanolamine, diethanolamine, triethanolamine, 2-methyl-2-amino-1-propanol.

May also be mentioned the salts formed by neutralization of the tertiary amine moieties, for example using a mineral or organic acid. Among the mineral acids include sulfuric acid or hydrochloric acid, hydrobromic acid, hydriodic acid, phosphoric acid, boric acid. Among the organic acids include acids having one or more carboxylic, sulfonic or phosphonic groups. It can be linear aliphatic, branched or cyclic or aromatic acids. These acids may also comprise one or more heteroatoms selected from O and N, for example in the form of hydroxyl groups. acetic acid may especially be mentioned or propionic acid, terephthalic acid, and citric acid and tartaric acid.

According to one embodiment of the invention, the grafted ethylenic polymer contains no additional non-acrylic vinyl monomers as described above. In this embodiment, the insoluble skeleton of the grafted ethylenic polymer is formed only from acrylic monomers as described above.

It is understood that these non-polymerized acrylic monomers may be soluble in the dispersion medium under consideration, but the polymer formed with these monomers is insoluble in the dispersion medium.

According to a particular embodiment of the invention, the grafted ethylenic polymer is obtainable by radical polymerization in an organic polymerization medium: - a main acrylic monomer chosen from (meth) acrylates C1 C3, alone or mixed, and optionally one or more additional acrylic monomers chosen from acrylic acid, methacrylic acid and alkyl (meth) acrylates of formula (I) defined below, and salts, to form the said insoluble skeleton; and

- and ^ u-less-one silicone macromonomer comprising a polymerizable terminal-group, as defined above.

As a main acrylic monomer, there can be used methyl acrylate, methyl methacrylate, ethyl acrylate, ethyl methacrylate, n-propyl methacrylate, n-propyl acrylate iso-propyl methacrylate, iso-propyl, and mixtures thereof.

Most preferred is methyl acrylate, methyl methacrylate, ethyl methacrylate.

The additional acrylic monomers may be chosen from:

- (meth) acrylic acid and its salts,

- (meth) acrylates of formula (I) and salts thereof:

H, C = C COOR '

| (I)

in which :

- R 'denotes a hydrogen atom or a methyl group;

- R 2 represents

- a linear or branched alkyl group comprising 1 to 6 carbon atoms, said group comprising in its chain one or more oxygen atoms and / or having one or more substituents selected from

-OH, halogen atoms (F, Cl, Br, I) and -NR'R "with R 'and R" are identical or different, chosen from linear or branched C-1-C3;

- a cyclic alkyl group having 3 to 6 carbon atoms, said group possibly comprising in its chain one or more oxygen atoms and / or possibly comprising one or more substituents selected from OH and halogen atoms (F, Cl , Br, I);

- and mixtures thereof.

A. title ^ examples of R 2 include methoxyethyl, _éthoxyéthyle, _ trifluoroethyl; 2-hydroxyethyl, 2-hydroxypropyl, dimethylaminoethyl, diethylaminoethyl, dimethylaminopropyl.

Among these additional acrylic monomers, mention may be made most particularly (meth) acrylic acid, (meth) acrylates, methoxyethyl or ethoxyethyl; trifluoroethyl methacrylate; dimethylaminoethyl methacrylate, diethylaminoethyl methacrylate, 2-hydroxypropyl methacrylate, 2-hydroxyethyl acrylate, 2-hydroxypropyl acrylate, 2-hydroxyethyl, salts thereof, and mixtures thereof. Most preferred is acrylic acid, methyl acrylic acid.

The macromonomers comprise at one end of the chain a polymerizable end group capable of reacting during the polymerization with the acrylic monomers and optionally the additional vinyl monomers, to form the side chains of the grafted ethylenic polymer. Said polymerizable terminal group may be in particular a vinyl group or (meth) acrylate (or (meth) acryl), and preferably a (meth) acrylate.

The macromonomers are preferably chosen from macromonomers whose homopolymer has a glass transition temperature (Tg) less than or equal to 25 ° C, especially ranging from - 100 ° C at 25 ° C, preferably from - 80 ° C to 0 ° C.

The macromonomers have a weight average molecular weight greater than or equal to 200, preferably greater than or equal to 300, preferably greater than or equal to 500, more preferably greater than 600. Preferably the macromonomers have a weight average molecular mass by weight ( Mw) ranging from 200 to 100 000, preferably from 500 to 50,000, preferably from 800 to 20,000, more preferably from 800 to 10,000, and even more preferably from 800 to 6,000.

In the present application, the weight average molecular weight (Mw) and number (Mn) are determined by liquid chromatography by gel permeation (solvent - THF - -courbe- calibration established -with linear polystyrene standards , refractometric detector).

Carbon-based macromonomers can in particular be mentioned: - (i) homopolymers and copolymers of (meth) acrylate, linear or branched C8-C22, containing a polymerizable end group chosen from vinyl or (meth) acrylate among which may be mentioned in particular: the macromonomers of poly (acrylate 2-ethylhexyl) a mono (meth) acrylate; the macromonomers of poly (dodecyl acrylate) or poly (dodecyl methacrylate) in a mono (meth) acrylate; macromonomers poly (stearyl acrylate) or poly (stearyl methacrylate) in a mono (meth) acrylate.

Such macromonomers are described in EP895467 and EP96459 patents and in the article Gillman KF, Polymer Letters, Vol 5, page 477-481 (1967).

Mention may in particular be made of poly-based macromonomers (ethyl acrylate, 2-hexyl) or poly (dodecyl acrylate) end to mono (meth) acrylate.

- (ii) polyolefins having a terminal ethylenically unsaturated group, in particular having a terminal group (meth) acrylate. Examples of such polyolefins include in particular the following macromonomers, it being understood that they have a terminal (meth) acrylate: polyethylene macromonomers, polypropylene macromonomers, the macromonomers of polyethylene / polypropylene copolymer macromonomers, polyethylene / polybutylene copolymer macromonomers, polyisobutylene; polybutadiene macromonomers; polyisoprene macromonomers; polybutadiene macromonomers; the macromonomers of poly (ethylene / butylene) -polyisoprene

Such macromonomers are described in particular in US5625005 which mentions ethylene / butylene and ethylene / propylene reactive end group (meth) acrylate.

Mention may in particular be made of poly methacrylate (ethylene / butylene), such as that marketed under the name Kraton Liquid L-1253 from Kraton Polymers. Silicone-based macromonomers can be made in particular of polydimethylsiloxane terminal group to mono (meth) acrylate, and in particular those of formula (II):

wherein Rβ is a hydrogen atom or a methyl group; R denotes a divalent hydrocarbon group having 1 to 10 carbon atoms and optionally contains one or two ether bonds -O-; R10 denotes an alkyl group having 1 to 10 carbon atoms, especially from 2 to 8 carbon atoms; n denotes an integer from 1 to 300, preferably ranging from 3 to 200 and preferentially ranging from 5 to 100.

Silicone-based macromonomers can be used monomethacryloxypropyl polydimethylsiloxanes such as those sold under the name PS560- K6 by the company United Chemical Technologies Inc. (UCT) or under the name MCR-M17 by Gelest Inc.

Preferably, the polymerized macromonomer (constituting the side chains of the graft polymer) is from 0.1 to 15% by weight of the total polymer weight, preferably 0.2 to 10% by weight, more preferably from 0.3 to 8% by weight.

As particularly preferred grafted ethylenic polymer dispersed in a non-silicone liquid fatty phase, one can use those obtained by polyméiisation __:

- methyl acrylate and polyethylene / polybutylene macromonomer containing methacrylate end group (especially Kraton L-1253), particularly in a solvent chosen from isododecane, isononyl isononanoate, octyldodecanol, malate diisostearyl, an alkyl benzoate Cι 2 -C 15 (such as Finsolv TN); - of methoxyethyl acrylate and of the macromonomer polyethylene / polybutylene methacrylate end group at (especially Kraton L-1253), in particular in isododecane;

- methyl acrylate monomer / methyl methacrylate and the macromonomer polyethylene / polybutylene methacrylate end group (especially Kraton L-1253), in particular in isododecane;

- methyl acrylate / acrylic acid monomers and of the macromonomer polyethylene / polybutylene methacrylate end group (especially Kraton L-1253), in particular in isododecane; - methyl acrylate monomers / dimethylaminoethyl methacrylate and of the macromonomer polyethylene / polybutylene methacrylate end group (especially Kraton L-1253), in particular in isododecane;

- methyl acrylate monomers methacrylate / 2-hydroxyethyl and polyethylene / polybutylene macromonomer containing methacrylate end group (especially Kraton L-1253), in particular in isododecane.

As particularly preferred grafted acrylic polymer dispersed in a silicone liquid fatty phase, one can use those obtained by polymerization: of methyl acrylate and monomethacryloxypropylpolydimethylsiloxane macromonomer having an average molecular weight ranging from 800 to 6000, in particular in decamethylcyclopentasiloxane or phenyl trimethicone;

- methyl acrylate, acrylic acid and monomethacryloxypropylpolydimethylsiloxane macromonomer having an average molecular weight ranging from 800 to 6000, in particular in decamethylcyclopentasiloxane or phenyl trimethicone.

Preferably, the graft polymer has a weight average molecular weight (Mw) -comprise -between 10-000 -et-300 000, especially between 20 and 2-00- 000- 000, more preferably between 25 000 and 150 000

Thanks to the above characteristics, in an organic medium of given dispersion polymers have the ability to fold on themselves, thus forming substantially spherical particles, with the periphery of these particles having the deployed side chains, which ensure the stability of these particles. Such particles resulting from the characteristics of the graft polymer has the particularity of not agglomerating in the said medium and therefore being self-stabilized and form a particularly stable dispersion of polymer particles.

In particular, the grafted ethylenic polymers of the dispersion can form nanoscale particles of average size ranging from 10 to 400 nm, preferably from 20 to 200 nm. Due to this very small size, the graft polymer particles in dispersion are particularly stable and therefore unlikely to form agglomerates.

The graft polymer dispersion may be a stable dispersion and not form sediments when placed over a prolonged period (e.g. 24 hours) at room temperature (25 ° C).

Preferably, the particle dispersion 'of graft polymer has a solids content (or dry extract) of polymer ranging from 40% to 70% by weight of solids and especially from 45% to 65% by weight.

the polymer dispersion particles grafted with a method can be prepared comprising a step of free-radical copolymerization, in an organic polymerization medium, one or more acrylic monomers as defined above with one or more macromonomers as defined above.

As indicated above, the liquid organic dispersion medium may be the same or different from the polymerization medium.

D'UNE conventionally - copolymerization can be effectuée- in presence- of a polymerization initiator. The polymerization initiators may be free radical initiators. Generally, such a polymerization initiator can be selected from organic peroxy compounds such as dilauroyl peroxide, dibenzoyl peroxide, tert-butyl peroxy-2- ethylhexanoate; diazo compounds such as azobisisobutyronitrile, azobisdiméthylvalero nitrile.

The reaction may also be initiated using photoinitiators or with radiation such as UV, neutrons or plasma.

In general, to implement this method, are introduced into a suitably sized reactor to the amount of polymer which will perform at least part of the organic polymerization medium, part of the acrylic monomers and / or additional vinyl, which will, after polymerization, the insoluble skeleton, all of the macromonomer (which will constitute the side chains of the polymer) and a portion of the polymerization initiator. At this point of introduction, the reaction mixture forms a relatively homogeneous medium.

The reaction medium is then stirred and heated to a temperature to obtain polymerization of the monomers and MACROMONOMERS. After some time, the initially homogeneous and clear medium leads to a milky dispersion. Then a mixture consisting of the remaining part of the monomers and the polymerization initiator. After an adequate time during which the mixture is heated under stirring, the medium stabilizes in the form of a milky dispersion, the dispersion comprising polymer particles stabilized in the medium in which they were created, the said stabilization being due to the presence in the polymer, soluble side chains in said dispersion medium.

The graft polymer described above may be present in the composition according to the invention in a content ranging from 0.5% to 45% by weight, based on the total weight of the composition, preferably ranging from 1% to 30% by weight and preferentially ranging from 2% to 25% by weight.

- The -according to-the-invention composition may comprise one or colorants. selected from water-soluble dyes and pulverulent dyestuffs, for instance 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, based on the weight of the composition, preferably from 0.01% to 30% by weight.

By pigments are to be understood particles of any form, white or colored, mineral - or organic, insoluble in the physiological medium, intended to color the composition.

Pearlescent agents should be understood as meaning iridescent particles of any form, especially produced by certain mollusks in their shell or synthesized.

10 The pigments may be white or colored, inorganic and / or organic. Mention may be made, among inorganic pigments, titanium dioxide, optionally surface-treated, zirconium oxide or cerium oxide, and also zinc oxide, iron oxide (black, yellow or red) or chromium oxide, violet manganese, ultramarine blue, chromium hydrate and ferric blue, and metal powders such as aluminum powder or copper powder.

Among the organic pigments, carbon black include, type of the D & C pigments, and lakes based on cochineal carmine, barium, strontium, calcium and aluminum.

20 may also include effect pigments such as particles comprising an organic or inorganic substrate, natural or synthetic, for example glass, acrylic resins, polyester, polyurethane, polyethylene terephthalate, ceramics or aluminas, the said substrate being coated with metallic substances such as aluminum, gold, silver, platinum, copper, bronze, or metal oxides such as titanium dioxide, iron oxide, oxide chromium and mixtures thereof.

The pearlescent pigments can be chosen from white pearlescent pigments such

- - - -that-le-coated mica-deJitane, or de.bismuth oxychloride, pigments._nacr_és_

30 such as colored titanium mica coated with iron oxides, titanium mica coated especially with ferric or blue and chromium oxide, titanium mica coated with an organic pigment of the abovementioned type, and nacreous pigments based bismuth oxychloride. . One can also use interference pigments, in particular liquid crystal or multilayer.

Advantageously, the grafted polymer present in the composition according to the invention allows to obtain a good homogeneous dispersion of pulverulent coloring materials such as pigments or pearlescent agents.

The invention therefore also relates to a foundation composition comprising a dispersion of particles of grafted ethylenic polymer in a liquid fatty phase, as described above, and at least one dyestuff, especially pigments, nacres, or another optical effect dependent.

Water-soluble dyes are, for example, beetroot juice, methylene blue.

The composition according to the invention may additionally comprise one or more fillers, especially in a content ranging from 0.01% to 50% by weight, based on the total weight of the composition, preferably ranging from 0.01% to 30% by weight. Fillers should be understood to mean particles of any form, colorless or white, mineral or synthetic, insoluble in the medium of the composition irrespective of the temperature at which the composition is manufactured. These fillers serve especially to modify the rheology or 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.). There may be mentioned talc, mica, silica, kaolin, polyamide (Nylon®) powder (Orgasol from Atochem), poly -de-β-alanine and polyethylene, the -polymers powders -from - tetrafluoroethylene (Teflon®), lauroyl-lysine, starch, boron nitride, hollow polymer microspheres such as those of polyvinylidene chloride / acrylonitrile, for instance Expancel® (Nobel Industrie), acrylic acid copolymers (Polytrap® from Dow Corning) and silicone resin microbeads (Tospearls® from Toshiba, for example), elastomeric polyorganosiloxane particles, precipitated calcium carbonate, magnesium carbonate, magnesium hydrogen carbonate, the hydroxyapatite, hollow silica microspheres (silica Beads® from Maprecos), glass microcapsules or ceramic, and metal soaps derived from organic carboxylic acids having from 8 to 22 carbon atoms, preferably 12 to 18 carbon atoms, for exam ple zinc stearate, magnesium or lithium, zinc laurate or magnesium myristate.

0 The composition of the invention may also contain ingredients commonly used in cosmetics, such as vitamins, moisturizers, emollients, free-radical scavengers, thickeners, trace elements, softeners, sequestering agents, fragrances , basifying or acidifying agents, preservatives, sunscreens, surfactants, antioxidants, gums, waxes, propellants, or mixtures thereof.

Of course, those skilled in the art should select this or these optional additional compounds and / or their quantity, such that the advantageous properties of the corresponding composition according to the invention are not 0 or not substantially, impaired by the addition envisaged.

The composition according to the invention may especially be in the form of suspension, dispersion, solution, gel, emulsion, especially an oil-in-water emulsion (O / W) or water-in-oil (W / H ) or multiple (W / O / W or polyol / O / W or O / W / O), as a cream, paste, foam, dispersion of vesicles, especially of ionic or nonionic lipids, two-phase lotion or multiphase, spray, powder, paste. The composition may be anhydrous, for example it may be a stick or an anhydrous paste. The composition may be a composition not - - rincée.- - 0

The skilled person may select the appropriate dosage form and its method of preparation, on the basis of his general knowledge, taking into account both the nature of the constituents used, especially their solubility in the support, and secondly to the application envisaged for the composition.

According to another aspect, the invention also relates to a cosmetic assembly comprising: i) a container delimiting at least one compartment, said container being closed by a closing member; and ii) a composition placed inside said compartment, the composition being in accordance with the invention.

The container can be in any appropriate form. It may especially be in the form of a bottle, a tube, a jar, a pouch, a box, a sachet or a box.

The closure member may take the form of a removable stopper, a lid, a cover, a tear-off strip or a capsule, in particular of the type comprising a body fixed to the container and a cap articulated on the body. It can also be in the form of a member for selectively closing the container, especially a pump, a valve, or a valve.

The container may be combined with an applicator, especially in the form of a block of foam or of elastomer, a felt or a spatula. The applicator may be free (tuft or sponge) or secured to a rod borne by the closing member, as described for example in US Patent 5 492 426. The applicator may be secured to the receptacle, as described eg FR 2761959.

The product may be contained directly in the container, or indirectly. For example, the product can be arranged on an impregnated support, especially sub-form of a wipe, or a buffer, - and-arranged (individually or in plurality) in a box or -dans- A sachet. Such a support incorporating the product is described for example in WO 01/03538. The closing member may be coupled to the container by screwing. Alternatively, the coupling between the closing member and the container is done other than by screwing, especially via a bayonet mechanism, by snap-fastening, gripping, welding, bonding or by magnetic attraction. By "snap" in particular means any system involving the crossing of a bead or cord of material by elastic deformation of a portion, especially of the closing member, followed by return elastically unstressed position of said portion after the crossing of the bead or cord.

The container may be at least partly made of thermoplastic material. Examples of thermoplastic materials include polypropylene or polyethylene.

Alternatively, the container is made of non-thermoplastic material, especially glass or metal (or alloy).

The container may have rigid walls or deformable walls, especially in the form of a tube or a tubular bottle.

The container may comprise means for causing or facilitating the distribution of the composition. For example, the container may have deformable walls so as to cause the output composition in response to an excess pressure inside the container, this positive pressure being caused by elastic (or non-elastic) of the container walls . Alternatively, especially when the product is in the form of a stick, the latter can be driven by a piston mechanism. Always in the case of a stick, especially of makeup product (lipstick, foundation, etc.), the container may comprise a mechanism, especially a rack or with a threaded stem, or with a helical ramp, and capable of moving a stick in the direction of said ouverture.- such a mechanism is described, for example, in patent FR-2 806-273 or in patent FR 2 775 566. such a mechanism for a liquid product is described in patent FR 2 727 609. the container may consist of a carton with a base delimiting at least one housing containing the composition, and a lid, especially articulated on the base and adapted to cover at least partially said bottom. Such a carton is described, for example in WO 03/018423 or in patent FR 2 791 042.

The container may be equipped with a drainer arranged in the vicinity of the container opening. Such a drainer makes it possible to wipe the applicator and possibly the rod to which it may be secured. Such a drainer is described, for example in the patent FR 2,792,618.

The composition may be at atmospheric pressure inside the container (at room temperature) or pressurized, especially by means of a propellant gas (aerosol). In the latter case, the container is equipped with a valve (of the type used for aerosols).

The content of the patents or patent applications mentioned above are incorporated by reference herein.

The invention will now be described in greater detail in light of the following examples given for illustrative and not restrictive.

The present examples illustrate the preparation of polymers according to the invention, capable of forming a particle dispersion in an organic medium under consideration.

In these examples, it is determined, after preparation of said dispersion, the weight average molecular weight (Mw) and number (Mn) of the polymer, the glass transition temperature of the polymer, the solids content (or dry extract) of the dispersion and the size of the polymer particles.

The weight average molecular weight (Mw) and number (Mn) are determined by liquid chromatography by gel permeation (THF solvent, calibration curve established with linear polystyrene standards, refractometric detector). The measurement of the glass transition temperature (Tg) is performed according to ASTM D3418-97, by differential scanning calorimetry (DSC "Differential Scanning Calorimetry") on a calorimeter, over a temperature range between -100 ° C and +150 ° C at a heating rate of 10 ° C / min in aluminum crucibles of 150 .mu.l.

Preparing crucibles are as follows: in an aluminum crucible of 150 .mu.l was charged with 100 .mu.l of the resulting dispersion and the solvent is allowed to evaporate for 24 hours at room temperature and 50% relative humidity. The operation is repeated then introduced the crucible in the Mettler DSC30 calorimeter.

Dry matter content (or dry extract), i.e. the non-volatile content, can be measured in several ways: there may be mentioned, for example, methods by oven drying or drying methods by exposure to infrared radiation.

Preferably, the dry matter content is measured by heating the sample with infrared rays of 2 .mu.m to 3.5 .mu.m wavelength. The substances contained in the composition that have a high vapor pressure evaporate under the effect of this radiation. The measurement of sample weight loss is used to determine the solids content of the composition. These measurements are performed using an LP16 commercial infrared desiccator from Mettler. This technique is fully described in the machine documentation supplied by Mettler.

The measurement protocol is the following: is spread about 1 g of the composition to a metal cup. The latter, after introduction into the dryer, is subjected to a set temperature of 120 ° C for one hour. The wet mass of the sample, corresponding to the initial mass and dry mass of échantillon.-corresponding to the mass after exposure to radiation, - are- measured using a precision balance.

The dry matter content is determined as follows: Solids = 100 x (dry / wet weight mass). The particle sizes can be measured by different techniques include in particular light scattering techniques (dynamic and static), Coulter counter methods, measurements by sedimentation rate (linked to the size via the law Stokes) and microscopy. These techniques can measure a particle diameter and for some of them a particle size distribution.

Preferably, the sizes and size distributions of particles of the compositions of the invention are measured by static light scattering using a type of commercial granuiomètre MasterSizer 2000 from Malvern. The data is processed on the basis of the Mie scattering theory. This theory, exact for isotropic particles, to determine in the case of non-spherical particles, an "effective" diameter particles. This theory is described especially in the Van de Hulst, HC, "Light Scattering by Small Particles," Chapters 9 and 10, Wiley, New York, 1957. The composition is characterized by its "effective" diameter by volume D [4,3], defined as follows:

where Vj represents the volume of dj effective particle diameter. This parameter has been described in the technical documentation of granuiomètre. The measurements are performed at 25 ° C, on a dilute particle dispersion obtained from the composition as follows: 1) dilution by a factor of 100 with water, 2) homogenization of the solution, 3) rest of the solution for 18 hours, 4) recovering the supernatant whitish homogeneous. The "effective" diameter is obtained by taking a refractive index of 1, 33 for water and an average refractive index of 1, 42 for the particles.

The invention is further illustrated by the examples described below.

Example 1 This example illustrates the preparation of a polymer forming a dispersion of particles in a carbon-based solvent, said polymer being obtained by polymerization of methyl acrylate, acrylic acid and the macromonomer corresponding to a polyethylene / polybutylene copolymer (Kraton L -1253).

In a 1 liter reactor was charged with 200 g of heptane, 200 g of isododecane, 14g of methyl acrylate, 10 g acrylic acid, 16 g of macromonomer copolymer type polyethylene / polybutylene methacrylate end group (Kraton L-1253) and 3.2 g of tert-butyl peroxy-2-ethylhexanoate (Trigonox 21S). Was stirred and heated the reaction mixture at room temperature to 90 ° C over 1 hour. After 15 minutes at 90 ° C, there is a change in appearance of the reaction medium, which passes from a transparent appearance to a milky appearance. Heating with stirring was maintained for another 15 minutes then added dropwise over one hour a mixture consisting of 130 g of methyl acrylate, 30 g of acrylic acid and 2 g of Trigonox 21S

then allowed to heat for 4 hours at 90 ° C then the heptane is distilled from the reaction medium. At the end of this distillation operation, a dispersion of polymer particles thus prepared stable in isododecane

The characteristics of the polymer and the particles formed by said polymer are as follows:

- Molecular weight Mw = 175,294

- Molecular weight Mn = 28265

- Polydispersity index (Mw / Mn) = 6.2

theoretical dry extract: 54.9% in isododecane

- particle size: 85 nm with polydispersity of 0.04, performed on a Malvern Autosizer Lo-C at 25 ° C;

The graft polymer comprises 8% by weight of macromonomer relative to the weight of the polymer.

The stability of the dispersion obtained is highlighted by the implementation of the following stability protocol: In a test tube were placed 8 mL of the formed dispersion and centrifuged at 4000 rpm / min for 15 minutes with a centrifuge Jouan C100-S5. After 15 minutes, it is found that there is no phase separation, which demonstrates that the dispersion is stable.

EXAMPLE 2

This example illustrates the preparation of a polymer forming a dispersion of particles in a silicone solvent, said polymer being obtained by polymerization of methyl acrylate, acrylic acid and monomethacryloxypropyl polydimethylsiloxane macromonomer having a weight average molecular weight of 5,000 sold under the name MCR-M17 by Gelest Inc.

In a 1 liter reactor was charged with 200 g of heptane, 200 g of decamethylcyclopentasiloxane, 26 g of methyl acrylate, 14 g monomethacryloxypropylpolydimethylsiloxane MCR-M17 and 3.2 g of t-butylperoxy-2-éthyIhexanoate (Trigonox 21S ).

Stirred and the reaction mixture heated to 90 ° C over 1 hour. After 15 minutes at 90 ° C, there is a change in appearance of the reaction medium, which passes from a transparent appearance to a milky appearance. Heating with stirring was maintained for an additional 15 minutes and then dropwise added for 1 hour a mixture consisting of 120 g of methyl acrylate, 40 g of acrylic acid and 2 g of Trigonox 21S is then allowed heating for 4 hours at 90 ° C then the heptane is distilled from the reaction medium. At the end of this distillation operation, a polymer particle dispersion was obtained and prepared stable in decamethylcyclopentasiloxane

(Therefore sidechain solubie in D5) relative to the weight of the polymer.

The characteristics of the polymer and the particles formed by the said polymer are as follows: - Solids content: 50% in decamethylcyclopentasiloxane performed by thermal

- Glass transition: 12 ° C by DSC Mettler

- particle size: 170 nm with polydispersity of 0.04, performed on a Malvern Autosizer Lo-C at 25 ° C

Example 3:

This example illustrates the preparation of a polymer forming a dispersion of particles in a carbon-based solvent, said polymer being obtained by polymerization of methyl acrylate, acrylic acid and the macromonomer corresponding to a polyethylene / polybutylene copolymer (Kraton L-1253 ).

In a 1 liter reactor was charged with 200 g of heptane, 200 g of isododecane, methyl acrylate, 14g, 10g of acrylic acid and 16 g of macromonomer copolymer type polyethylene / polybutylene (Kraton L-1253 ) and 3.2 g of tert-butyl peroxy-2-ethylhexanoate (Trigonox 21S).

Was stirred and heated the reaction mixture at room temperature to 90 ° C over 1 hour. After 15 minutes at 90 ° C, there is a change in appearance of the reaction medium, which passes from a transparent appearance to a milky appearance. Heating with stirring was maintained for another 15 minutes then added dropwise over one hour a mixture consisting of 70 g of methyl acrylate, 90 g of acrylic acid and 2 g of Trigonox 21S

then allowed to heat for 4 hours at 90 ° C then the heptane is distilled from the reaction medium. At the end of this distillation operation, a dispersion of polymer particles thus prepared stable in isododecane

The characteristics of the polymer and the particles formed by said polymer are as follows:

- Molecular weight Mw = not characterizable by GPC

- Molecular Weight Mn = not characterizable by GPC

- Polydispersity index (Mw / Mn) by GPC = not characterizable theoretical dry extract: 53.6% in isododecane - Grain size: not measured

The graft polymer comprises 8% by weight of macromonomer relative to the weight of the polymer.

After implementation of the stability protocol in accordance with Example 1, it is found that the dispersion obtained is stable.

Example 4:

This example illustrates the preparation of a polymer forming a dispersion of particles in a carbon-based solvent, said polymer being obtained by polymerization of methyl acrylate, acrylic acid and the macromonomer corresponding to a polyethylene / polybutylene methacrylate end groups ( Kraton L-1253).

In a 1 liter reactor was charged with 200 g of heptane, 200 g of isododecane, 28 g of methyl acrylate and 12 g of macromonomer copolymer type polyethylene / polybutylene methacrylate end groups (Kraton L-1253) and 3.2 g of tert-butyl peroxy-2-ethylhexanoate (Trigonox 21S). Was stirred and heated the reaction mixture at room temperature to 90 ° C over 1 hour. After 15 minutes at 90 ° C, there is a change in appearance of the reaction medium, which passes from a transparent appearance to a milky appearance. Heating with stirring was maintained for another 15 minutes then added dropwise over one hour a mixture consisting of 150 g of methyl acrylate, 10 g of acrylic acid and 2 g of Trigonox 21S

Then allowed -on-heating for 4 hours at-90-G-heptane then distilled - - the reaction medium. At the end of this distillation operation, a dispersion of polymer particles thus prepared stable in isododecane

The graft polymer comprises 6% by weight of macromonomer relative to the weight of the polymer.

The characteristics of the polymer and the particles formed by said polymer are as follows:

- Molecular weight Mw = 143639

- Molecular weight Mn = 23965

- Polydispersity index (Mw / Mn) = 5.99

- theoretical dry extract: 51.3% in isododecane

- particle size: 48 nm with polydispersity of 0.04, performed on a Malvern Autosizer Lo-C at 25 ° C;

After implementation of the stability protocol in accordance with Example 1, it is found that the dispersion obtained is stable.

Example 5:

This example illustrates the preparation of a polymer forming a dispersion of particles in a silicone oil, said polymer being obtained by polymerization of methyl acrylate and of the macromonomer monomethacryloxypropylpolydimethylsiloxane having an average molecular weight of 5,000 sold under the name MCR-M17 by Gelest Inc.

In a 1 liter reactor was charged with 200 g of heptane, 200 g of decamethylcyclopentasiloxane, 30 g of methyl acrylate, 10 g of monomethacryloxypropylpolydimethylsiloxane MCR-M17 and 3.2 g of tertiobutyiperoxy-2-ethylhexanoate (Trigonox 21S ). 0 .. n has gjte -and we -chauffe-le reaction mixture at 90 ° C in 1 -heure.- After -15 minutes at 90 ° C, there is a change in appearance of the reaction medium, which passes from a transparent appearance to a milky appearance. Heating is maintained under stirring for a further 15 minutes then added dropwise over one hour a mixture consisting of 160 g of methyl acrylate and 2 g of Trigonox 21S is then allowed to heat for 4 hours at 90 ° C then the heptane is distilled from the reaction medium.

At the end of this distillation operation, a polymer particle dispersion was obtained and prepared stable in decamethylcyclopentasiloxane (D5).

The graft polymer comprises 5% by weight of macromonomer (and therefore soluble in the side chain D5) with respect to the polymer weight.

The characteristics of the polymer and the particles formed by said polymer are as follows:

- Molecular weight Mw = 102347

- Molecular weight Mn = 28283

- Polydispersity index (Mw / Mn) = 3.62

- Solids: 51, 4% in D5 performed by thermal

- Glass transition: 12 ° C by DSC Mettler

- particle size: 160 nm with polydispersity of 0.04, performed on a Malvern Autosizer Lo-C at 25 ° C

After implementation of the stability protocol in accordance with Example 1 shows that the dispersion is stable.

The polymers of Examples 1-5 include the following monomers, their rates are reported in percentage by weight of the polymer:

Examples 6-10

5 foundations were prepared having the following compositions (the contents are indicated in percent based on the total weight of the composition):

Each composition contains 2.1% by weight of active material of the graft polymer. -

ingredients:

ABIL EM 97: silicone mixture oxyethylenated oxypropylenated substituted α-ω / cyclomethicone (85:15) sold by the company Goldschmidt

Inwitor 780 K: Mono-diglycerides of iso-steraique esterified acid by succinic acid, sold by the company Sasol

D5: cyclopentasiloxane

silicone gum: blend polydiphényl dimethylsiloxane and cyclopentasiloxane (15/85) sold under the name MIRASIL C (DPDM by Rhodia

nylon powder sold under the name Orgasol 2002 Extra D NAT COS by Atofina

10% of pigments include:

1, 43% of yellow iron oxides coated tri-isostearoyl titanate, isopropyl

(BYO-I 2 Kobo)

0.46% brown iron oxides coated tri-isostearoyl isopropyl titanate (BRO-I

2 Kobo)

0.22% of black iron oxides coated tri-isostearoyl isopropyl titanate (BBO-I

2 Kobo)

7.89% titanium dioxide coated isostearoyl tri-isopropyl titanate (BTD-

401 Kobo)

Followed by measuring the transfer index in the presence of sebum of each composition according to the measurement protocol described above. We obtained the following results:

It is noted that the compositions have a transfer index in the presence of sebum of less than 4. In addition, the compositions of Examples 6-8 have better resistance to the transfer in the presence of sebum that the compositions of Examples 9 and 10. It is thus found that the presence of acrylic acid in the grafted polymer promotes the transfer resistance of the deposit obtained with the composition property.

Claims

1. Cosmetic composition for making or skin care composition comprising a dispersion of particles of a grafted ethylenic polymer in a liquid fatty phase, the composition being capable of forming a deposit that has a transfer index in the presence of sebum of less than 4.
2. Composition according to claim 1, characterized in that the deposit has a transfer index in the presence of less than or equal sebum to 3, preferably less than or equal to 2.
3. Composition according to claim 1 or 2, characterized in that the deposit has a transfer index in the presence of sebum of less than or equal to 1, 5, preferably less than or equal to 1.
4. Composition according to any one of the preceding claims, characterized in that the grafted ethylenic polymer comprises an ethylenic backbone insoluble in the said liquid fatty phase and side chains covalently bound to said backbone and soluble in the said liquid fatty phase.
5. Composition according to any one of the preceding claims, characterized in that the grafted ethylenic polymer is a grafted acrylic polymer.
6. A composition according to any preceding claim, characterized in. in that the ethylene polymer is dispersed in the absence of additional surface stabilizer particles of the graft polymer.
7. Composition according to any one of the preceding claims, characterized in that the dispersed grafted ethylenic polymer is an acrylic polymer obtainable by radical polymerization in an organic polymerization medium: - at least one acrylic monomer and optionally at least one non-acrylic vinyl monomer to form the said insoluble skeleton; and
- at least one macromonomer comprising a polymerizable end group to form the side chains, the said macromonomer having a weight average molecular weight greater than or equal to 200 and the content of polymerized macromonomer representing from 0.05 to 20% by weight of the polymer .
8. Composition according to the preceding claim, characterized in that the acrylic monomer is chosen, alone or as a mixture, the following monomers and their salts:
- (i) (meth) acrylates of formula:
CH, COOR 2
R 1 wherein:
- R denotes a hydrogen atom or a methyl group;
- R 2 represents a group selected from:
- a linear or branched alkyl group comprising 1 to 6 carbon atoms, said group possibly comprising in its chain one or more heteroatoms selected from O, N and S; and / or possibly comprising one or more substituents selected from -OH, halogen atoms (F, Cl, Br, I) and - NR'R "with R 'and R" are identical or different, chosen from linear or branched alkyl C1-C4 alkyl; and / or may be substituted by at least one polyoxyalkylene group, in particular polyoxyethylene and / or polyoxypropylene, said polyoxyalkylene group consisting of the repetition of 5 to 30 oxyalkylene units;
- a cyclic alkyl group having 3 to 6 carbon atoms, said group possibly comprising in its chain one or more heteroatoms selected from O, N and S, and / or possibly comprising one or more substituents selected from OH and atoms halogen (F, Cl, Br, I);
- (ii) (meth) acrylamides of formula: in which :
- R 3 denotes a hydrogen atom or a methyl group;
- R 4 and R 5, identical or different, represent a hydrogen atom or an alkyl group, linear or branched, having 1 to 6 carbon atoms, possibly comprising one or more substituents selected from -OH, atoms halogen (F, Cl, Br, I) and -NR'R "with R 1 and R" are identical or different, chosen from linear or branched alkyls C- | -C4; or
- R 4 represents a hydrogen atom and R 5 represents a 1, 1-dimethyl-3-oxobutyl;
- (Ni) the (meth) acrylic monomers comprising at least one carboxylic, phosphoric or sulfonic acid, such as acrylic acid, methacrylic acid, acrylamidopropanesulfonic acid:
9. Composition according to claim 7 or 8, characterized in that the acrylic monomer is selected from methyl (meth) acrylates, ethyl, propyl, butyl, isobutyl; (meth) acrylates, methoxyethyl or ethoxyethyl; trifluoroethyl methacrylate; dimethylaminoethyl methacrylate, diethylaminoethyl methacrylate, (met) acrylate, 2-hydroxybutyl (meth) acrylate, 2-hydroxyethyl; dimethylaminopropyl; (meth) acrylic acid; and their salts.
10. Composition according to any one of claims 7 to 9, characterized in that the acrylic monomer is selected from methyl acrylate, methoxyethyl acrylate, methyl methacrylate, 2-hydroxyethyl methacrylate, the (meth) acrylic acid, dimethylaminoethyl methacrylate, and mixtures thereof.
11. Composition according to any one of claims 7 to 10, characterized in that the grafted polymer comprises (meth) acrylic acid.
12. Composition according to any one of claims 7 to 11, characterized in that the acrylic monomers comprise at least (meth) acrylic acid and at least one monomer chosen from (meth) acrylates and (meth) acrylamides described in points (i) and (ii) in claim 8.
13. Composition according to any one of claims 7 to 12, characterized in that the acrylic monomers comprise at least (meth) acrylic acid and at least one monomer chosen from (meth) acrylates, C1- C3.
14. Composition according to any one of the preceding claims, characterized in that (meth) acrylic acid is present in an amount of at least 5% by weight, based on the total polymer weight, especially ranging from 5 % to 80 wt%, preferably at least 10% by weight, especially from 10 wt% to 70 wt%, preferably at least 15% by weight, especially ranging from 15% to 60% by weight.
15. Composition according to any one of claims 7 to 14, characterized in that the grafted acrylic polymer does not contain additional non-acrylic vinyl monomer.
16. Composition according to any one of claims 7 to 15, characterized in that the grafted acrylic polymer is obtainable by radical polymerisation of one or more monomer (s) acrylic acid (s) and a a or more monomer (s) additional (s) vinyl (s) non-acrylic (s), and said macromonomer.
- 1-7. -Composition-. according. une__ -quelconque ___de_s. claims 7 to. 14 and j_6, _ characterized in that the non-acrylic vinyl monomers are selected from:
- the vinyl esters of the formula: R 6 -COO-CH = CH 2 wherein Rβ represents a linear or branched alkyl group comprising from 1 to 6 atoms, or a cyclic alkyl group having 3 to 6 carbon atoms and / or an aromatic group, for example of benzene, anthracene or naphthalene;
- non-acrylic vinyl monomers comprising at least one carboxylic, phosphoric or sulfonic acid, such as crotonic acid, maleic anhydride, itaconic acid, fumaric acid, maleic acid, styrenesulfonic acid, vinylbenzoic acid, vinylphosphoric acid and the salts thereof;
- non-acrylic vinyl monomers comprising at least one tertiary amine function, such as 2-vinylpyridine, 4-vinylpyridine;
- and mixtures thereof.
18. Composition according to any one of claims 7 to 17, characterized in that the acrylic monomers represent from 50 to 100% by weight, preferably from 60 to 100% by weight, preferably from 70 to 100% by weight of mixing acrylic monomers + optional non-acrylic vinyl monomers.
19. Composition according to any one of claims 7 to 18, characterized in that the macromonomer comprises, at one end of the chain a polymerizable end group chosen from a vinyl group or a (meth) acrylate, and preferably a (meth) acrylate.
20. Composition according to any one of claims 7 to 19, characterized in that the macromonomer has a weight average molecular weight of greater than or equal to 300, preferably greater than or equal to 500, more preferably greater than 600.
21; - Composition according to any one of claims 7 to 16, -caractérisée in that the macromonomer has a weight average molecular weight (Mw) ranging from 200 to 100 000, preferably from 500 to 50 000, preferentially ranging from 800-20 000 more preferably from 800 to 10,000, and even more preferably from 800 to 6,000.
22. Composition according to any one of claims 7 to 20, characterized in that the polymerized macromonomer represents from 0.1 to 15% by weight of the total polymer weight, preferably 0.2 to 10% by weight, and preferably from 0.3 to 8% by weight,
23. Composition according to any one of the preceding claims, characterized in that the liquid fatty phase comprises a liquid organic compound chosen from: - liquid organic compounds having an overall solubility parameter according to the Hansen solubility space or equal to 18 (MPa) 1/2, monoalcohols having a global solubility parameter according to the space of n illuubbiilliittéé ooff HHaannssen less than or equal to 20 (MPa) 1/2; and mixtures thereof.
24. Composition according to the preceding claim, characterized in that the said liquid organic compound is a non-volatile oil.
25. Composition according to any one of the preceding claims, characterized in that the liquid fatty phase is a non-silicone liquid fatty phase.
26. Composition according to the preceding claim, characterized in that the non-silicone liquid fatty phase comprises at least 50% by weight of at least one non-silicone liquid organic compound chosen from:
- the non-silicone liquid organic compounds having an overall solubility parameter according to the Hansen solubility space or equal to 18 (MPa) 1/2;
- liquid monoalcohols having an overall solubility parameter in the Hansen- solubility space or equal to 20 (MPa) / 2; and - mixtures thereof.
27. The composition of claim 25 or 26, characterized in that the non-silicone liquid fatty phase comprises less than 50% by weight of silicone liquid organic compounds having an overall solubility parameter according to the Hansen solubility space of less than or equal to 18 (MPa) 1 2.
28. The composition of claim 25 or 26, characterized in that the non-silicone liquid fatty phase does not contain a silicone-based liquid organic compounds.
29. Composition according to any one of claims 25 to 28, characterized in that the macromonomer is a macromonomer carbon.
30. Composition according to the preceding claim, characterized in that the carbon maeromonomère is selected from:
- (i) homopolymers and copolymers of acrylate or alkyl methacrylate linear or branched C8-C22 and having a polymerizable end group chosen from vinyl or (meth) acrylate;
- (ii) polyolefins having a terminal polymerizable ethylenically unsaturated group.
31. The composition of claim 29 or 30, characterized in that the carbon macromonomer is chosen from:
- (i) macromonomers of poly (acrylate 2-ethylhexyl) a mono (meth) acrylate; the macromonomers of poly (dodecyl acrylate) to end ι ιono (meth) acrylate; the macromonomers of poly (dodecyl methacrylate); macromonomers poly (stearyl acrylate) a mono (meth) acrylate; the macromonomers of poly (stearyl methacrylate) in a mono (meth) acrylate;
- (ii) polyethylene macromonomers, polypropylene macromonomers, -les- macromonomer polyethylene / polypropylene copolymer, - the macromonomer polyethylene / polybutylene copolymer, polyisobutylene macromonomers, polybutadiene macromonomers, polyisoprene macromonomers, the macromonomers polybutadiene macromonomers poly (ethylene / butylene) -polyisoprene, these macromonomers having a terminal group (meth) acrylate.
32. A composition according to any one of claims 29 to 31, characterized in that the carbon macromonomer is chosen from:
- (i) macromonomers of poly (ethyl acrylate-2-ethylhexyl) mono end (meth) acrylate, poly macromonomers (dodecyl acrylate) a mono (meth) acrylate;
- (ii) poly methacrylate (ethylene / butyl ene!).
10
33. Composition according to any one of claims 29 to 32, characterized in that the grafted polymer is selected from polymers obtainable by polymerizing:
- methyl acrylate and of the macromonomer polyethylene / polybutylene methacrylate end groups, particularly in a solvent chosen from isododecane, isononylisononanoate, octyldodecanol, diisostearyl malate, benzoate alkyl Cι 2 - C- |5;
- of methoxyethyl acrylate and of the macromonomer polyethylene / polybutylene methacrylate end groups, in particular in isododecane;
20 - monomers methyl acrylate / methyl methacrylate and the macromonomer polyethylene / polybutylene methacrylate end groups, in particular in isododecane;
- methyl acrylate / acrylic acid monomers and of the macromonomer polyethylene / polybutylene methacrylate end groups, in particular in isododecane;
- monomers methyl acrylate / dimethylaminoethyl methacrylate and of the macromonomer polyethylene / polybutylene methacrylate end groups, in particular in isododecane;
-.- - of. acrylate monomers. methyl / methacrylate. -2-hydroxyethyl _and the.
30 macromonomer polyethylene / polybutylene methacrylate end groups, in particular in isododecane.
34. Composition according to any one of claims 25 to 33, characterized in that the grafted polymer is a grafted non-silicone polymer.
35. Composition according to the preceding claim, characterized in that the non-silicone grafted polymer predominantly containing a carbon-based macromonomer and optionally containing at most 7% by weight of the total polymer weight, of silicone macromonomer.
36. The composition of claim 34 or 35, characterized in that the grafted silicone polymer is free of carbon-based macromonomer.
37. A composition according to any one of claims 1 to 24, characterized in that the liquid fatty phase is a silicone liquid fatty phase.
38. Composition according to the preceding claim, characterized in that the silicone liquid fatty phase consists of at least 50% by weight of at least one silicone liquid organic compound chosen from silicone liquid organic compounds having an overall solubility parameter according to the Hansen solubility space of less than or equal to 18 (MPa) 1/2.
39. The composition of claim 27 or 38, characterized in that the organic liquid silicone compound comprises a volatile silicone oil.
40. Composition according to the preceding claim, characterized in that the volatile silicone oil is chosen from octamethylcyclotetrasiloxane, decamethylcyclopentasiloxane, dodecamethylcyclohexasiloxane, heptamethylhexyltrisiloxane, heptamethyloctyltrisiloxane, Poctaméthyltrisiloxane, decamethyltetrasiloxane, and mixtures thereof.
41. The composition of claim 27 or 38, characterized in that the organic liquid silicone compound comprises a nonvolatile silicone oil.
42. Composition according to the preceding claim, characterized in that the non-volatile silicone oil is chosen from non-volatile polydialkylsiloxanes; polydimethylsiloxanes comprising alkyl, alkoxy or phenyl groups, pendent or at the end of a silicone chain, these groups containing from 2 to 24 carbon atoms; phenylated silicones; polysiloxanes modified with fatty acids (in particular C 8 -C 20), fatty alcohols (in particular C 8 -C 20) or polyoxyalkylenes (especially polyoxyethylene and / or polyoxypropylene); aminated polysiloxanes; polysiloxanes containing hydroxyl groups; fluoro polysiloxanes comprising a fluoro group that is pendent or at the silicone chain having from 1 to 12 carbon atoms of which some or all of hydrogen are substituted by fluorine atoms; and mixtures thereof.
43. Composition according to any one of claims 37 to 42, characterized in that the liquid fatty phase comprises less than 50% by weight of organic compounds non-silicone liquid.
44. The composition of claim 26 or 43, characterized in that the non-silicone liquid organic compound is selected from non-silicone liquid organic compounds having an overall solubility parameter according to the Hansen solubility space of less than 18 (MPa) 1 2; liquid monoalcohols having an overall solubility parameter according to the Hansen solubility space or
1/2 equal to 20 (MPa); and mixtures thereof.
45. Composition according to the preceding claim, characterized in that the non-silicone organic liquid compound having a global solubility parameter according to the Hansen solubility space or equal to 18 (MPa) 1/2 is selected from carbon-based oils , hydrocarbon, fluorinated, alone or mixed; linear alkanes, branched and / or cyclic, optionally volatile; esters and in particular -the. esters, linear. -ramifiés or cyclic, having .to carbon moins..6..atomes._; ketones and in particular ketones having at least 6 carbon atoms; ethers and in particular ethers having at least 6 carbon atoms.
46. The composition of claim 23 or 44, characterized in that the monoalcohols having a global solubility parameter according to the Hansen solubility space of less than or equal to 20 (MPa) 1/2 are selected from aliphatic fatty monoalcohols having 6 to 30 carbon atoms, the hydrocarbon chain not comprising a substitution group, and in particular oleyl alcohol, decanol, and linoleyl alcohol.
47. Composition according to any one of the preceding claims, characterized in that the liquid fatty phase comprises a non-volatile silicone oil.
48. Composition according to the preceding claim, characterized in that the non-silicone volatile oil is chosen from isododecane, isodecane and isohexadecane.
49. Composition according to any one of claims 37 to 46, characterized in that the liquid fatty phase does not contain non-silicone liquid organic compounds.
50. Composition according to any one of the preceding claims, characterized in that the nonvolatile oil is present in a content ranging from 0.1% to 80% by weight, based on the total weight of the composition, and preferably ranging from 3% to 50% by weight.
51. Composition according to any one of the preceding claims, characterized in that it comprises a volatile oil in a content ranging from 1% to 90% by weight, based on the total weight of the composition, and preferably ranging from 5% to 70% by weight.
52. Composition according to any one of claims 37 to 51, characterized in that the macromonomer is a silicone macromonomer.
53. Composition according to the preceding claim, characterized in that the silicone macromonomer is an organopolysiloxane macromonomer and preferably a polydimethylsiloxane macromonomer.
54. The composition of claim 52 or 53, characterized in that the macromonomer is chosen from polydimethylsiloxanes containing terminal group mono (meth) acrylate, including monomethacryloxypropyl polydimethylsiloxane.
55. Composition according to any one of claims 52 to 54, characterized in that the silicone macromonomer is chosen from macromonomers of formula (II):
wherein Rs denotes a hydrogen atom or a methyl group; Ro denotes a divalent hydrocarbon group having 1 to 10 carbon atoms and optionally contains one or two ether bonds -O-; R10 denotes an alkyl group having de.1 to 10 carbon atoms, especially from 2 to 8 carbon atoms; n denotes an integer from 1 to 300, preferably ranging from 3 to 200 and preferentially ranging from 5 to 100.
56. Composition according to any one of claims 37 to 55, characterized in that the grafted acrylic polymer is obtainable by free radical polymerization in the polymerization medium: - a main acrylic monomer chosen from (meth ) alkyl acrylates, C1-C3, alone or mixed, and optionally one or more additional acrylic monomers chosen from acrylic acid, n and I acryliqu -they .. (meth) acrylates of formula (I):
H, C = C - COOR ',
(I) wherein:
- R'ι denotes a hydrogen atom or a methyl group;
- R 2 represents
- a linear or branched alkyl group comprising 1 to 6 carbon atoms, said group comprising in its chain one or more oxygen atoms and / or having one or more substituents selected from
-OH, halogen atoms (F, Cl, Br, I) and -NR'R "with R 'and R", identical or different, chosen from linear or branched C1-C3 alkyls;
- a cyclic alkyl group having 3 to 6 carbon atoms, said group possibly comprising in its chain one or more oxygen atoms and / or possibly comprising one or more substituents selected from OH and halogen atoms (F, Cl , Br, I);
and salts thereof, to form the said insoluble skeleton; and
- and a silicone macromonomer.
57. Composition according to the preceding claim, characterized in that R 2 denotes a group chosen from the methoxyethyl, ethoxyethyl, trifluoroethyl; 2-hydroxyethyl, 2-hydroxypropyl, dimethylaminoethyl, diethylaminoethyl, dimethylaminopropyl.
58. The composition of claim 56 or 57, characterized in that the main acrylic monomer is chosen from methyl (meth) acrylate, (meth) acrylate, (meth) acrylate, n-propyl, (meth) isopropyl acrylate, and mixtures thereof.
.
59 .__ Compo.sition- according-l'.une-any-of claims 56- 58, characterized in that the main acrylic monomer is chosen from methyl acrylate, methyl methacrylate, methacrylate ethyl.
60. The composition of claim 56, characterized in that the additional acrylic monomer is chosen from (meth) acrylic acid, (meth) acryla6e methoxyethyl (meth) acrylate, ethoxyethyl, trifluoroethyl methacrylate, dimethylaminoethyl methacrylate, diethylaminoethyl methacrylate, (meth) acrylate, 2-hydroxybutyl (meth) acrylate, 2-hydroxyethyl, and salts thereof.
61. The composition of claim 56 or 60, characterized in that the additional acrylic monomer is chosen from acrylic acid, methacrylic acid.
62. Composition according to any one of claims 37 to 61, characterized in that the grafted polymer is selected from polymers obtained by polymerization: of methyl acrylate and of the macromonomer monomethacryloxypropylpolydimethylsiloxane having an average molecular weight ranging from 800 6000, especially in decamethylcyclopentasiloxane or phenyl trimethicone;
- methyl acrylate, acrylic acid and monomethacryloxypropylpolydimethylsiloxane macromonomer having an average molecular weight ranging from 8Û0 6000, in particular in decamethylcyclopentasiloxane or phenyl trimethicone.
63. Composition according to any one of claims 37 to 62, characterized in that the grafted polymer is a grafted silicone polymer.
64. Composition according to the preceding claim, characterized in that the grafted silicone polymer predominantly contains a silicone macromonomer and conte_nan.t_éve_ntue.ll.em.ent .to more- 7% by weight, poids_to.taLdu._p.olymère, of carbon-based macromonomer.
65. The composition of claim 63 or 64, characterized in that the grafted silicone polymer is free of carbon-based macromonomer.
66. Composition according to any one of the preceding claims, characterized in that the graft polymer has a weight average molecular weight (Mw) of between 10,000 and 300,000, in particular between 20 000 and 200 000, more preferably between 25 000 and 150 000.
67. Composition according to any one of the preceding claims, characterized in that the grafted polymer particles have an average size ranging from 10 to 400 nm, preferably from 20 to 200 nm.
68. Composition according to any one of the preceding claims, characterized in that the grafted ethylenic polymer is a film-forming polymer.
69. Composition according to any one of the preceding claims, characterized in that the graft polymer is present in a content ranging from 0.5% to 45% by weight, based on the total weight of the composition, preferably ranging from 1% to 30% by weight and preferentially ranging from 2% to 25% by weight.
70. Composition according to any one of the preceding claims, characterized in that it comprises a dyestuff.
71. Composition according to the preceding claim, characterized in that the coloring material is a pulverulent dyestuff, in particular chosen from pigments and nacres.
72. A composition according to any preceding claim, characterized in what comprises a cosmetic ingredient .parmiJes-Select. vitamins, moisturizers, emollients, free-radical scavengers, thickeners, trace elements, softeners, sequestering agents, fragrances, basifying or acidifying agents, preservatives, sunscreens, surfactants, anti-oxidants, gums, waxes, propellants, or mixtures thereof.
73. Cosmetic composition according to any one of the preceding claims, characterized in that it is in the form of suspension, dispersion, solution, gel, emulsion, especially an oil-in-water emulsion (O / W) or water-in-oil (W / O) or multiple (W / O / W or polyol / O / W or O / W / O), as a cream, a paste, a mousse, a dispersion of vesicles, especially of ionic or nonionic lipids, two-phase or multiphase lotion, spray, powder.
74. Cosmetic composition according to any one of the preceding claims, characterized in that it is in anhydrous form.
75. Composition according to any one of the preceding claims, characterized in that the composition is a skin makeup product.
76. Make-up foundation comprising a composition according to any preceding claim.
77. foundation composition comprising a dispersion of particles of a grafted ethylenic polymer in a liquid fatty phase as defined according to one of claims 1 to 69, and a colorant including pigments, pearlescent agents or any other optical effect dependent.
78. Cosmetic assembly comprising: a) a container delimiting at least one compartment, said container being closed by a closing member; and b) a composition placed inside the said compartment, the composition being c-çjifoime.à r_un.e.-qu-elα ^^ -
79. Cosmetic assembly according to the preceding claim, characterized in that the container is formed, at least partly, at least one thermoplastic material.
80. Cosmetic assembly according to Claim 78, characterized in that the container is formed, at least partly, at least one non-thermoplastic material, especially glass or metal.
81. An assembly according to any one of claims 78 to 80 characterized in that, in the closed position of the container, the closing member is screwed onto the container.
82. An assembly according to any one of claims 78 to 80 characterized in that, in the closed position of the container, the closing member is coupled to the container other than by screwing, especially by snap-fastening, bonding or welding.
83. An assembly according to any one of claims 78-82, characterized in that the composition is substantially at atmospheric pressure inside the compartment.
84. An assembly according to any one of claims 78 to 83, characterized in that the composition is pressurized inside the container.
85. Cosmetic process for making or skin care comprising applying to skin a cosmetic composition according to one of claims 1-77.
86. Use of a composition according to one of claims 1 to 77, for obtaining a deposit, especially a make-up, on the skin with good transfer resistance, especially in the presence of sebum.
87. Use, in a cosmetic composition, of a dispersion of particles of a grafted ethylenic polymer in dispersion in a liquid fatty phase, the composition being particularly suitable for forming a film having a deposit that has a transfer index in the presence of sebum less than 4, to obtain a deposit, especially a make-up, on the skin with good transfer resistance, especially in the presence of sebum.
EP20030813184 2002-12-12 2003-12-12 Cosmetic composition comprising a polymer Withdrawn EP1585777A2 (en)

Priority Applications (7)

Application Number Priority Date Filing Date Title
FR0215737 2002-12-12
FR0215738 2002-12-12
FR0215739 2002-12-12
FR0215737A FR2848558B1 (en) 2002-12-12 2002-12-12 acrylic polymer, said dispersion stable polymer in a nonaqueous organic medium and composition comprising said dispersion
FR0215738A FR2848559B1 (en) 2002-12-12 2002-12-12 acrylic polymer, said dispersion stable polymer in a nonaqueous organic medium and non-silicone composition comprising said dispersion.
FR0215739A FR2848560B1 (en) 2002-12-12 2002-12-12 acrylic polymer, said dispersion stable polymer in a nonaqueous organic medium and silicone composition comprising said dispersion.
PCT/FR2003/003708 WO2004055073A3 (en) 2002-12-12 2003-12-12 Cosmetic composition comprising a polymer

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EP1585777A2 true true EP1585777A2 (en) 2005-10-19

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EP20030813184 Withdrawn EP1585777A2 (en) 2002-12-12 2003-12-12 Cosmetic composition comprising a polymer
EP20030813183 Withdrawn EP1572770A2 (en) 2002-12-12 2003-12-12 Cosmetic composition comprising a polymer
EP20030813190 Active EP1572137B1 (en) 2002-12-12 2003-12-12 Non-transfer cosmetic composition comprising a dispersion of particles of a silicone-free grafted ethylene polymer in a liquid fatty phase
EP20030813186 Withdrawn EP1583784A2 (en) 2002-12-12 2003-12-12 Non-transfer cosmetic composition comprising a dispersion of a grafted ethylene polymer

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EP20030813183 Withdrawn EP1572770A2 (en) 2002-12-12 2003-12-12 Cosmetic composition comprising a polymer
EP20030813190 Active EP1572137B1 (en) 2002-12-12 2003-12-12 Non-transfer cosmetic composition comprising a dispersion of particles of a silicone-free grafted ethylene polymer in a liquid fatty phase
EP20030813186 Withdrawn EP1583784A2 (en) 2002-12-12 2003-12-12 Non-transfer cosmetic composition comprising a dispersion of a grafted ethylene polymer

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US (3) US20060251601A1 (en)
EP (4) EP1585777A2 (en)
JP (5) JP2006509811A (en)
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WO (8) WO2004055079A3 (en)

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JP2006509812A (en) 2006-03-23 application
WO2004055077A2 (en) 2004-07-01 application
JP2006509810A (en) 2006-03-23 application
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WO2004055077A3 (en) 2004-08-05 application
EP1572137B1 (en) 2017-03-15 grant
WO2004055074A3 (en) 2004-08-05 application
WO2004055079A2 (en) 2004-07-01 application
US7794695B2 (en) 2010-09-14 grant
EP1583784A2 (en) 2005-10-12 application
ES2627551T3 (en) 2017-07-28 grant
WO2004055073A3 (en) 2004-08-05 application
WO2004055074A2 (en) 2004-07-01 application
US20060134034A1 (en) 2006-06-22 application
WO2004055081A3 (en) 2004-08-05 application
WO2004055082A2 (en) 2004-07-01 application
WO2004055080A2 (en) 2004-07-01 application
WO2004055079A3 (en) 2004-08-12 application
WO2004055077A8 (en) 2005-08-25 application
WO2004055080A3 (en) 2004-08-12 application
JP2008201803A (en) 2008-09-04 application
WO2004055073A2 (en) 2004-07-01 application
WO2004055081A2 (en) 2004-07-01 application
US20060127341A1 (en) 2006-06-15 application
WO2004055078A1 (en) 2004-07-01 application
JP4167229B2 (en) 2008-10-15 grant
US20060251601A1 (en) 2006-11-09 application
JP2006509809A (en) 2006-03-23 application
WO2004055082A3 (en) 2004-09-10 application
JP2006509811A (en) 2006-03-23 application
EP1572137A2 (en) 2005-09-14 application

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