WO2004041150A2 - Composition contenant un polymere semi-cristallin et une huile polyester - Google Patents

Composition contenant un polymere semi-cristallin et une huile polyester Download PDF

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Publication number
WO2004041150A2
WO2004041150A2 PCT/EP2003/015019 EP0315019W WO2004041150A2 WO 2004041150 A2 WO2004041150 A2 WO 2004041150A2 EP 0315019 W EP0315019 W EP 0315019W WO 2004041150 A2 WO2004041150 A2 WO 2004041150A2
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WIPO (PCT)
Prior art keywords
oil
semi
composition
composition according
polymer
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PCT/EP2003/015019
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English (en)
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WO2004041150A3 (fr
Inventor
Véronique Ferrari
Nathalie Julien
Sylvie Guillard
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L'oreal
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Priority claimed from FR0213890A external-priority patent/FR2846552B1/fr
Application filed by L'oreal filed Critical L'oreal
Priority to AU2003294028A priority Critical patent/AU2003294028A1/en
Publication of WO2004041150A2 publication Critical patent/WO2004041150A2/fr
Publication of WO2004041150A3 publication Critical patent/WO2004041150A3/fr

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • A61K8/817—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen; Compositions or derivatives of such polymers, e.g. vinylimidazol, vinylcaprolactame, allylamines (Polyquaternium 6)
    • A61K8/8176—Homopolymers of N-vinyl-pyrrolidones. Compositions of derivatives of such polymers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/37—Esters of carboxylic acids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • A61K8/8105—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
    • A61K8/8111—Homopolymers or copolymers of aliphatic olefines, e.g. polyethylene, polyisobutene; Compositions of derivatives of such polymers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • A61K8/8141—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • A61K8/8152—Homopolymers or copolymers of esters, e.g. (meth)acrylic acid esters; Compositions of derivatives of such polymers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q1/00—Make-up preparations; Body powders; Preparations for removing make-up

Definitions

  • the present invention relates to a composition, especially a cosmetic composition, containing at least one semi-crystalline polymer and an oil comprising at least two ester functions, referred to as a "polyester oil", which is especially in the form of a stick and which gives a comfortable, glossy deposit when applied.
  • a cosmetic composition containing at least one semi-crystalline polymer and an oil comprising at least two ester functions, referred to as a "polyester oil”, which is especially in the form of a stick and which gives a comfortable, glossy deposit when applied.
  • the subject of the invention is a composition with improved heat stability. This composition also allows the application of a glossy, non-sticky, non- migrating film with good covering power onto keratin materials .
  • Patent application FR-Al-0001004 discloses the combination of a polyester oil and of a hetero atom-containing polymer of the polyamide type in wax- ⁇ free lipstick compositions. That document does not teach that a polyester oil makes it possible to improve the heat stability of compositions on keratin materials .
  • compositions whose fatty phase is gelled with semi-crystalline polymers have been described in the as yet unpublished patent application FR 01/06047.
  • the lipstick formulations derived from these inventions are in the form of a stick that deposits a glossy, non-sticky, covering film. These compositions however have the drawback of being sensitive to temperature changes. This is reflected by ' poor stability when the sticks are applied at a temperature above room temperature. The stick tends to become crushed.
  • Patents US 5 736 125 and US 5 156 911, and also patent application WO 01/19333, illustrate certain types of semi-crystalline polymer that may be introduced into the composition of the formulations of the invention.
  • these documents do not describe cosmetic compositions and do not suggest that the addition of a particular polyester oil can improve the stability of the compositions .
  • the Applicant has found that the addition of a polyester oil to a composition containing a semi-crystalline polymer makes it possible to improve the heat stability of the composition.
  • the invention applies in particular to lip makeup products, but also to eye makeup products, for instance eyeliners, in particular in pencil form, and mascaras especially in cake form, or skin makeup products, for instance foundations.
  • the composition of the invention is a makeup composition containing a) at least one liquid fatty phase structured with at least one semi-crystalline polymer having an organic structure, the melting point of which is greater than or equal to 30°C, chosen from homopolymers and copolymers bearing at least one crystallizable side chain, b) a dyestuff, and c) a polyester oil, the liquid fatty phase, the dyestuff, the polyester oil and the polymer forming a physiologically acceptable medium.
  • the composition of the invention contains a) a blend of at least one polymer chosen from low- melting polymers with a melting point of greater than 30°C and less than 50°C, and of at least one polymer chosen from high-melting polymers with a melting point at least equal to 50°C, b) a polyester oil, the liquid fatty phase, the polyester oil and the polymer blend forming a physiologically acceptable medium.
  • polymers means compounds containing at least two repeating units, preferably at least three repeating unit ' s and more especially at least ten repeating units .
  • the term "polymers” means compounds containing at least two repeating units, preferably at least three repeating unit ' s and more especially at least ten repeating units .
  • the term “polymers” means compounds containing at least two repeating units, preferably at least three repeating unit ' s and more especially at least ten repeating units .
  • “semi-crystalline polymer” means polymers comprising a crystallizable portion and an amorphous portion in the skeleton and having a first-order reversible change of phase, in particular of melting (solid-liquid transition) .
  • the crystallizable portion is either a side chain (or pendent chain) or a block in the skeleton.
  • the melting point of the semi-crystalline polymer is preferably less than 150°C.
  • the crystallizable portion is a block of the polymer skeleton
  • this crystallizable block has a different chemical nature to that of the amorphous blocks; in this case, the semi-crystalline polymer is a block copolymer, for example of the diblock, triblock or multiblock type.
  • the semi- crystalline polymer may be a homopolymer or a copolymer.
  • the terms "organic compound” and “having an organic structure” mean compounds containing carbon atoms and hydrogen atoms, and possibly hetero atoms such as S, 0, N or P, alone or in combination.
  • the composition of the invention may be in the form of a paste, a solid or a cream. It may be an oil-in-water emulsion or a water-in-oil emulsion, or a solid or soft anhydrous gel. It is preferably in anhydrous form, and more especially in the form of an anhydrous gel, especially shaped as a stick or as a dish.
  • Semi-crystalline polymers The semi-crystalline polymer (s) of the composition of the invention advantageously comprise a weight-average molecular mass Mw ranging from 5 000 to 1 000 000, preferably from 10 000 to 800 000 and preferentially from 15 000 to 500 000.
  • the semi-crystalline polymer (s) according to the invention serving as structuring agent are solids at room temperature (25°C) and atmospheric pressure (760 mmHg) , with a melting point of greater than or equal to 30°C.
  • the melting point values correspond to the melting point measured using a differential scanning calorimeter (DSC) , such as the calorimeter sold under the name DSC 30 by the company Mettler, with a temperature rise of 5 or 10°C per minute (the melting point under consideration is the point corresponding to the' temperature of the most endothermic peak of the thermogra ) .
  • DSC differential scanning calorimeter
  • the semi-crystalline polymer (s) according to the invention preferably have a melting point that is higher than the temperature of the keratinous support intended to receive the said composition, in particular the skin or the lips.
  • the semi-crystalline polymer (s) according to the invention is (are) capable, alone or as a mixture, of structuring the composition without the addition of a particular surfactant or of filler or of wax.
  • the semi- crystalline polymers are advantageously soluble in the fatty phase, especially to at least 1% by weight, at a temperature that is higher than their melting point.
  • the blocks of the polymers are amorphous .
  • the expression "crystallizable chain or block” means a chain or block which, if it were obtained alone, would change from the amorphous state to the crystalline state reversibly, depending on whether one is above or below the melting point.
  • a “chain” is a group of atoms, which are pendent or lateral relative to the polymer skeleton.
  • a “block” is a group of atoms belonging to the skeleton, this group constituting one of the repeating units of the polymer.
  • the polymer skeleton of the semi- crystalline polymers is soluble in the liquid fatty phase.
  • the crystallizable blocks or chains of the semi-crystalline polymers represent at least 30% of the total weight of each polymer and better still at least 40%.
  • the semi-crystalline polymers containing crystallizable side chains are homopolymers or copolymers .
  • the semi-crystalline polymers of the invention containing crystallizable blocks are block or multiblock polymers . They may be obtained by polymerizing a monomer containing reactive (or ethylenic) double bonds or by polycondensation. When the polymers of the invention are polymers containing crystallizable side chains, these side chains are advantageously in random or statistical form.
  • the semi-crystalline polymers of the invention are of synthetic origin. According to one embodiment, they do not comprise a polysaccharide skeleton.
  • the composition contains a blend of at least one polymer chosen from low-melting polymers with a melting point of greater than 30°C and less than 50°C, and of at least one polymer chosen from high-melting polymers with a melting point at least equal to 50°C.
  • each of the semi-crystalline polymers of the polymer blend is advantageously independently chosen from: block copolymers of polyolefins of controlled crystallization, whose monomers are described in EP-A-0 951 897, polycondensates , especially of aliphatic or aromatic polyester type or of aliphatic/aromatic polyester type, - homopolymers or copolymers bearing at least one crystallizable side chain and homopolymers or copolymers bearing in the skeleton at least one crystallizable block, homopolymers or copolymers bearing at least one crystallizable side chain, in particular bearing fluoro group (s) , , and mixtures thereof .
  • the crystallizable side chain (s) or block (s) are hydrophobic.
  • the composition contains at least one liquid fatty phase structured with at least one semi- crystalline polymer having an organic structure, the melting point of which is greater than or equal to 30°C, chosen from homopolymers and copolymers bearing at least one crystallizable side chain.
  • They are homopolymers or copolymers comprising from 50% to 100% by weight of units resulting from the polymerization of .one or more monomers bearing a crystallizable hydrophobic side chain.
  • These homopolymers or copolymers are of any nature, provided that they meet the conditions mentioned hereinbelow with, in particular, the characteristic of being soluble or dispersible in the liquid fatty phase, by heating above their melting point mp. They can result: from the polymerization, especially the free- radical polymerization, of one or more monomers containing reactive or ethylenic double bond(s) with respect to a polymerization, namely a vinyl, (meth) acrylic or allylic group, from the polycondensation of one or more monomers bearing co-reactive groups (carboxylic acid, sulphonic acid, alcohol, amine or isocyanate) , such as, for example, polyesters, polyurethanes , polyethers, polyureas or polyamides .
  • co-reactive groups such as, for example, polyesters, polyurethanes , polyethers, polyureas or polyamides .
  • the crystallizable units (chains or blocks) of semi-crystalline polymers according to the invention are derived from monomer (s) containing crystallizable block(s) or chain(s), used for manufacturing semi-crystalline polymers. These polymers are chosen especially from homopolymers and copolymers resulting from the polymerization of at least one monomer containing crystallizable chain (s) that may be represented by formula X:
  • crystallizable chains "-S-C” may be aliphatic or aromatic, and optionally fluorinated or perfluorinated.
  • S especially represents a group (CH 2 ) n or (CH 2 CH 2 0) n or (CH 2 0) , which may be linear or branched or cyclic, with n being an integer ranging from 0 to 22.
  • n being an integer ranging from 0 to 22.
  • S is a linear group.
  • "S” and “C” are different.
  • the crystallizable chains are hydrocarbon-based aliphatic chains, they comprise hydrocarbon-based alkyl chains containing at least 11 carbon atoms and not more than 40 carbon atoms and better still not more than 24 carbon atoms. They are especially aliphatic chains or alkyl chains containing at least 12 carbon atoms, and they are preferably C 1 4-C 24 alkyl chains, preferably C ⁇ 6 -C22- When they are fluoroalkyl or perfluoroalkyl chains , they contain at least 11 carbon atoms, at least 6 of which carbon atoms are fluorinated.
  • the hydrocarbon-based and/or fluorinated crystallizable chains as defined above are borne by a monomer that may be a diacid, a diol, a diamine or a diisocyanate.
  • a monomer that may be a diacid, a diol, a diamine or a diisocyanate.
  • the polymers that are the subject of the invention are copolymers, they additionally contain from 0 to 50% of groups Y or Z resulting from the copolymerization: a) of Y which is a polar or non-polar monomer or a mixture of the two:
  • Y is a polar monomer, it is either a monomer bearing polyoxyalkylenated groups (especially oxyethylenated and/or oxypropylenated groups) , a hydroxyalkyl (meth) acrylate, for instance hydroxyethyl acrylate, (meth) acrylamide, an N-alkyl (meth) acrylamide, an N,N-dialkyl (meth) acrylamide such as, for example, N,N-diisopropylacrylamide or N-vinylpyrrolidone ( VP) , N-vinylcaprolactam, a monomer bearing at least one carboxylic acid group, for instance (meth) acrylic acid, crotonic acid, itaconic acid, maleic acid or fumaric acid, or bearing a carboxylic acid anhydride group, for instance maleic anhydride, and mixtures thereof.
  • polyoxyalkylenated groups especially oxyethylenated and/or oxy
  • Y When Y is a non-polar monomer, it may be an ester of the linear, branched or cyclic alkyl (meth) acrylate type, a vinyl ester, an alkyl vinyl ether, an alpha- olefin, styrene or styrene substituted with a Ci to Cio alkyl group, for instance a-methylstyrene, or a macromonomer of the polyorganosiloxane type containing vinyl unsaturation.
  • a non-polar monomer it may be an ester of the linear, branched or cyclic alkyl (meth) acrylate type, a vinyl ester, an alkyl vinyl ether, an alpha- olefin, styrene or styrene substituted with a Ci to Cio alkyl group, for instance a-methylstyrene, or a macromonomer of the polyorganosiloxane type containing vinyl uns
  • alkyl means a saturated group especially of C 8 to C 24 , except where otherwise mentioned.
  • ⁇ ) of Z which is a polar monomer or a mixture of polar monomers.
  • Z has the same definition as the "polar Y" defined above.
  • the semi-crystalline polymers containing a crystallizable side chain are alkyl
  • polymers that are soluble or dispersible in the liquid fatty phase by heating above their melting point mp.
  • These polymers are especially block copolymers consisting of at least two blocks of different chemical nature, one of which is crystallizable.
  • polymers defined in patent US-A-5 156 911 may be used; - Block copolymers of olefin or of cycloolefin containing a crystallizable chain, for instance those derived from the block polymerization of: cyclobutene, cyclohexene, cyclooctene, norbornene (i.e.
  • bicyclo (2 , 2 , 1) -2-heptene) 5-methylnorbornene, 5- ethylnorbornene, 5, 6-dimethylnorbornene, 5,5,6- tri ethylnorbornene, 5-ethylidenenorbornene, 5-phenylnorbornene, 5-benzylnorbornene, 5-vinylnor- bornene, 1,4,5, 8-dimethano-l, 2,3,4, 4a, 5, 8a- octahydronaphthalene, dicyclopentadiene, or mixtures thereof, with ethylene, propylene, 1-butene, 3-methyl-l- butene, 1-hexene, 4-methyl-1-pentene, 1-octene, 1-decene or 1-eicosene, or mixtures thereof, and in particular copoly(ethylene/norbornene) blocks and (ethylene/propylene/ethylidene-norbornene) block
  • the copolymers may be copolymers containing at least one crystallizable block, the copolymer residue being amorphous (at room temperature) . These copolymers may also contain two crystallizable blocks of different chemical nature.
  • the preferred copolymers are those that simultaneously contain at room temperature a crystallizable block and an amorphous block that are both hydrophobic and lipophilic, sequentially distributed; mention may be made, for example, of polymers containing one of the crystallizable blocks and one of the amorphous blocks below:
  • Block that is crystallizable by nature a) polyester, for instance poly (alkylene terephthalate) s, b) polyolefin, for instance polyethylenes or polypropylenes .
  • Amorphous and lipophilic block for instance: amorphous polyolefins or copoly (olefin) s such as poly (isobutylene) , hydrogenated polybutadiene or hydrogenated poly (isoprene) .
  • copolymers containing a crystallizable block and an amorphous block mention may be made of: a) poly(e-caprolactone) -b-poly (butadiene) block copolymers, preferably used hydrogenated, such as those described in the article D6 "Melting behavior of poly(-caprolactone) -block-polybutadiene copolymers" from S.
  • the semi-crystalline polymers in the composition of the invention may or may not be partially crosslinked, provided , that the degree of crosslinking does not interfere with their dissolution or dispersion in the liquid fatty phase by heating above their melting point. It may then be a chemical crosslinking, by reaction with a multifunctional monomer during the polymerization. It may also be a physical crosslinking which may, in this case, be due either to the establishment of bonds of hydrogen or dipolar type between groups borne by the polymer, such as, for example, the_ dipolar interactions between carboxylate ionomers, these interactions being of small amount and borne by the polymer skeleton; or to a phase separation between the crystallizable blocks and the amorphous blocks borne by the polymer.
  • the semi-crystalline polymers in the composition according to the invention are non- crosslinked.
  • the structuring semi- crystalline polymer that may be used in the composition according to the invention, mention may be made of the products Intelimer ® from the company Landec, described in the brochure "Intelimer ® polymers", Landec IP22 (Rev. 4-97) . These polymers are in solid form at room temperature (25°C) . They bear crystallizable side chains and have the formula X above.
  • the composition advantageously contains a blend of a polymer chosen from low-melting polymers with a melting point of greater than 30°C and less than 50°C, and of a polymer chosen from high-melting polymers with a melting point at least equal to 50°C.
  • the semi- crystalline polymer (s) with a melting point mp 2 of greater than 30°C and less than 50°C will be referred to as "low-melting polymers” and the crystalline or semi-crystalline compound (s) with a melting point m i of greater than or equal to 50°C will be referred to as "high-melting compounds”.
  • the melting point may be measured especially by any known method and in particular using a differential scanning calorimeter (DSC) .
  • DSC differential scanning calorimeter
  • the high-melting semi-crystalline compound(s) is (are) advantageously ' polymers with a melting point mpi such that 50°C ⁇ mpi ⁇ 150°C, better still 55°C ⁇ mpi ⁇ 150°C, and preferably 60°C ⁇ mpi ⁇ 130°C, and the low-melting polymers advantageously have a melting point mp 2 such that 30°C ⁇ mp 2 ⁇ 50°C and better still 35°C ⁇ mp 2 ⁇ 45°C.
  • This melting point is a temperature of first-order change of state.
  • the low-melting polymers have a melting point mp 2 at least equal to the temperature of the keratinous support intended to receive the composition according to the invention.
  • high-melting compounds that may be used in the invention, mention may be made of high-melting waxes, for instance certain polyethylene waxes such as Epolene N-14 sold by Eastman Chemical Co., carnauba waxes and certain microcrystalline waxes, for instance those sold by Tisco under the brand name "Tisco wax 88", and also high-melting semi-crystalline polymers.
  • the high-melting compound is a second high- melting organic solid semi-crystalline polymer.
  • crystalline polymers that are solid at room temperature, having a melting point of greater than 50°C [lacuna] random polymers comprising a controlled crystallization, as described in document EP-A-0 951 897, and more particularly the commercial products Engage 8 401 and Engage 8 402 from Dupont de Nemours, with melting points of 51°C and 64,°C respectively, which are ethylene/1-octene random bipolymers .
  • the semi-crystalline polymers with a melting point of less than 50°C are especially those described in Examples 3, 4, 5, 7 and 9 of patent US-A-5 156 911, containing a -COOH group, resulting from the copolymerization of acrylic acid and of a C5 to Ci ⁇ alkyl (meth) acrylate with a melting point ranging from 20°C to 35°C, and more particularly from the copolymerization: .
  • the semi-crystalline polymers with .a melting point of greater than or equal to 50°C are especially Intelimer described in the brochure "Intelimer® , polymers", Landec IP22 (Rev. 4-97) with a melting point of 56°C, which is an impermeable, non-sticky product that is viscous at room temperature.
  • the low-melting semi-crystalline polymers and/or those with a high melting point do not comprise a carboxylic group.
  • the high-melting compound (crystalline or semi-crystalline) and the low-melting compound are in a weight ratio ranging from 10/90 to 90/10, better still from 40/60 to 60/40 and more preferably in a weight ratio of close to 50/50.
  • the weight ratio of semi- ' crystalline polymer having an organic structure relative to the liquid fatty phase is from 0.20 to 0.60 and better still from 0.25 to 0.50, [lacuna] to obtain a hard stick that breaks down on contact with the skin or the lips, in particular having a hardness ranging from 100 to 350 gf.
  • the gelation of the fatty phase may be adjusted depending on the nature of the polymer (s) and their respective concentrations , and may be such that a rigid structure in the form of a tube or a stick is obtained.
  • the content of each polymer is chosen according to the desired hardness of the composition and as a function of the particular application intended.
  • the respective amounts of polymer may be such that they allow the production of a solid that can be broken down, in particular having a hardness ranging from 100 to 350 gf .
  • This hardness may be measured by the "cheese wire” method, which consists in cutting a tube of lipstick 12.7 mm in diameter and in measuring the hardness at 20°C, using a DFGHS 2 tensile testing machine from the company Indelco-Chatillon travelling at a speed of 100 mm/minute. It is expressed as the shear force (expressed as gramme-force) required to cut a stick under these conditions.
  • This hardness is such that the composition is self-supporting and can be broken down easily to form a satisfactory deposit on the skin and, the lips.
  • the composition of the invention in shaped form, especially in the form of a stick shows good impact strength.
  • the composition of the invention is preferably in the form of a solid stick with a hardness ranging from 100 gf to 350 gf, measured according to the "cheese wire" method.
  • an amount of semi-crystalline polymer such that the composition is in the form of a soft paste that can be applied by finger or using an applicator onto keratin materials .
  • the total amount of semi- crystalline polymer (s) represents from 0.1% to 80%, better still from 0.5% to 40% and even better still from 3% to 30% of the total weight of the composition. It preferably represents from 15% to 25% by weight of the composition.
  • the tubes or sticks according to the invention produce, after application, a glossy, non- sticky deposit of uniform colour that gives good coverage (i.e. the skin or the lips do not show through the makeup) .
  • Polyester oil
  • the polyester oil is a fatty substance that is liquid at room temperature (25°C) and atmospheric pressure (760 mmHg) , comprising at least two ester functions. It is preferably chosen from:
  • oils with a high content of triglycerides consisting of esters of fatty acids (of C 4 to C 24 ) and of glycerol, in which the fatty acids may have varied chain lengths, these chains possibly being linear or branched, and saturated or unsaturated; these oils are, in particular glyceryl triheptanoate, glyceryl trioctanoate; wheat germ oil, corn oil, sunflower oil, shea butter, castor oil, sweet almond oil, macadamia oil, apricot oil, soybean oil, rapeseed oil, cotton oil, alfalfa oil, poppy oil, pumpkin oil, sesame oil, marrow oil, avocado oil, hazelnut oil, grapeseed oil, blackcurrant seed oil, evening primrose oil, millet oil, barley oil, quinoa oil, olive oil, rye oil, safflower oil, candlenut oil, passionflower oil and musk rose oil; or alternatively caprylic/capric acid
  • polyol esters for instance propylene glycol dioctanoate, neopentyl glycol diheptanoate or diethylene glycol diisononanoate;
  • pentaer thritol esters for instance pentaerythrityl tetraisostearate
  • the polyester oil preferably represents from 5% to 30% by weight and preferably from 10% to 20% by weight of the composition.
  • the weight ratio of the polyester oil relative to the semi-crystalline polymer is advantageously between 0.2 and 1.1 and preferably between 0.4 and 0.9.
  • liquid fatty phase means a fatty phase that is liquid at room temperature (25°C) and atmosphere pressure (760 mmHg) , composed of one or more mutually compatible fatty substances that are liquid at room temperature, also known as oils. This fatty phase is macroscopically homogeneous.
  • the liquid fatty phase structured with the semi-crystalline polymers, constitutes the continuous phase of the .composition.
  • This fatty phase may contain one or more apolar or non- polar oils or a mixture of apolar oil(s) and of polar oil(s), other than the polyester oil described above.
  • the apolar oils according to the invention are in particular silicone oils such as linear or cyclic- polydimethylsiloxanes .
  • PDMS liquid at room temperature
  • phenyl silicones for instance phenyl trimethicones, phenyl dimethicones, phenyl tri ethylsiloxy diphenylsiloxanes, diphenyl dimethicones, diphenyl methyldiphenyl trisiloxanes, and 2-phenylethyl trimethylsiloxysilicates , which are liquid
  • linear or branched hydrocarbons or fluorocarbons of synthetic or mineral origin which are liquid, for instance liquid paraffins and derivatives thereof, petroleum jelly, polydecenes, hydrogenated polyisobutene such as Parleam® sold by the company Nippon Oil Fats, and squalane; mixtures thereof.
  • the apolar oils used are apolar oils of the liquid hydrocarbon-based type, of mineral or synthetic origin, chosen especially from Parleam® oil (hydrogenated isoparaffin) , isoparaffins and squalane, and mixtures thereof.
  • Parleam® oil hydrogenated isoparaffin
  • isoparaffins and squalane and mixtures thereof.
  • the liquid fatty phase advantageously contains at least one polar oil and at least one sparingly polar oil, for instance isononyl isononanoate.
  • the polar oils of the invention are : hydrocarbon-based plant oils with a high content of triglycerides consisting of fatty acid esters (of C 8 to C 2 4) of glycerol in which the fatty acids may have varied chain lengths, these chains possibly being linear or branched, and saturated or unsaturated; these oils are, in particular, wheat germ oil, corn oil, sunflower oil, shea butter, castor oil, sweet almond oil, macadamia oil, apricot oil, soybean oil, rapeseed oil, cotton oil, alfalfa oil, poppy oil, pumpkin oil, sesame oil, marrow oil, avocado oil, hazelnut oil, grapeseed oil, blackcurrant seed oil, evening primrose oil, millet oil, barley oil, quinoa oil, olive oil, rye oil, safflower oil, candlenut oil, passionflower oil and musk rose oil; or alternatively caprylic/capric acid triglycerides such as those sold by the company Stea
  • Miglyol 810, 812 and 818 by the company Dynamit Nobel synthetic oils of formula R5COOR6 in which R 5 represents a linear or branched superior fatty acid residue containing from 7 to 40 carbon atoms and R 6 represents a branched hydrocarbon-based chain containing from 3 to 40 carbon atoms, such as, for example, purcellin oil (cetostearyl octanoate) , isononyl isononanoate and Ci 2 ⁇ Ci 5 alkyl benzoate; synthetic esters and ethers, for instance isopropyl myristate, 2-ethylhexyl palmitate, alcohol or polyalcohol octanoates, decanoates or ricinoleates, and hydroxylated esters, for instance isostearyl lactate or diisostearyl malate; and pentaerythritol esters; fatty acids containing from 12 to 22 carbon atoms such as oleic acid, lin
  • the liquid fatty phase represents, in practice, from 5% to 99% and preferably from 20% to 80% of the total weight of the composition. It advantageously represents at least 60% of the total weight of the composition.
  • Dyestuff The composition advantageously contains a dyestuff, which may be chosen from the lipophilic dyes, hydrophilic dyes, pigments and nacres usually used in cosmetic or dermatological compositions, and mixtures thereof. This dyestuff is generally present in a proportion of from 0.01% to 50% (solids) and preferably from 5% to 30% of the total weight of the composition (if present) .
  • the liposoluble dyes are, for example, Sudan Red, D&C Red 17, D&C Green 6, ⁇ -carotene, soybean oil, Sudan Brown, D&C Yellow 11, D&C Violet 2, D&C Orange 5, quinoline yellow or methyl yellow. They can represent from 0% to 20% of the weight of the composition and better still from 0.01% to 6% (if present) .
  • the water- soluble dyes are, for example, beetroot juice or methylene blue, and can represent up to 6% of the total weight of the composition.
  • the pigments may be white or coloured, mineral and/or organic, and coated or uncoated.
  • mineral pigments which may be mentioned are titanium dioxide or zinc dioxide, optionally surface- treated, zirconium oxide or cerium oxide, as well as iron oxide, chromium oxide, manganese violet, ultramarine blue, chromium hydrate and ferric blue.
  • organic pigments which may be mentioned are carbon black, pigments of D&C type, and lakes based on cochineal carmine or on barium, strontium, calcium or aluminium (such as D & C Red 27, 21 or 7, D & C Yellow 5 or 6 and F D & C Blue No. 1) .
  • the pigments can represent from 0 to 40% (0.01% to 40%), especially from 0.5% to 35% and better still from 2% to 25% of the total weight of the composition (if present) .
  • the nacreous pigments may be chosen from white nacreous pigments such as mica especially coated with titanium or with bismuth oxychloride, coloured nacreous pigments such as titanium mica with iron oxides, titanium mica with, in ' particular, ferric blue or chromium oxide, titanium mica with an organic pigment of the type mentioned above, as well as nacreous pigments based on bismuth oxychloride. They can represent from 0 to 25% (0.05% to 25%) and better still from 0.1% to 15% of the total weight of the composition (if present) .
  • the pigments and nacres are introduced into the composition in the form of a pigmentary paste.
  • pigmentary paste means a concentrated colloidal dispersion of coated or uncoated coloured particles in a continuous medium, optionally stabilized using a dispersant.
  • a person skilled in the art will take care to select the optional additional additives and/or the amount thereof such that the advantageous properties of the composition according to the invention are not, or are not substantially, adversely affected by the envisaged addition.
  • the makeup composition of the invention may be in the form of a coloured product, in particular for the skin, optionally having care or treatment properties, and may be in particular a foundation, a blusher, a makeup rouge, an eyeshadow, a concealer product, an eyeliner or a body makeup product; a lip makeup product, for instance a lipstick, a lip gloss or a lip pencil, optionally with care or treatment properties; a makeup product for the integuments, for instance the nails, for the eyelashes in the form of a mascara, or for the eyebrows and the hair. It is preferably anhydrous and/or shaped, for example in cast form. Needless to say, the composition of the invention must be cosmetically acceptable, i.e.
  • the expression "cosmetically acceptable” means a composition of pleasant appearance, odour, feel and, where appropriate, taste. At least one wax such as those used to date in cosmetics may also be used in the composition of the invention.
  • a wax is a lipophilic fatty compound that is solid at room temperature (25°C) and at atmospheric pressure (760 mmHg) , which undergoes a reversible solid/liquid change of state, having a melting point of greater than 40°C and better still greater than 50°C, which may be up to 200°C, and having an anisotropic crystal organization in the solid state.
  • the size of the crystals is such that the crystals diffract and/or scatter light, giving the composition a cloudy, more or less opaque appearance.
  • the composition advantageously contains little or no standard waxes, especially less than 10% by weight and better still less than 5% by weight of standard wax relative to the total weight of the composition.
  • the standard waxes are those generally used in cosmetics and dermatology; they are especially of natural origin, for instance beeswax, candelilla wax, ouricury wax, Japan wax, cork fibre wax, sugar cane wax, paraffin wax, lignite wax, microcrystalline waxes with a melting point of greater than 50°C, lanolin wax, montan wax, ozokerites and hydrogenated oils such as hydrogenated jojoba oil, as well as waxes of synthetic origin, for instance polyethylene waxes derived from the polymerization of ethylene, waxes obtained by Fischer- Tropsch synthesis, with a melting point of greater than 50°C, fatty acid esters and glycerides that are solid at 50°C, and silicone waxes, for instance alkyl- and alkoxy-poly(di)methylsiloxanes and/or poly(di)methylsiloxane esters that are solid at 50°C.
  • the composition of the invention contains little or no "matting" fillers and in particular less than 5% of matting filler. This is especially the case when it is desired to obtain a glossy deposit on keratin materials such as the lips, the eyelashes and the hair.
  • fillers of this type may be used for a foundation.
  • a matting filler is generally a filler that absorbs the skin's sweat and/or sebum, for instance silicas > talcs, clays, kaolins and polyamide powders (Nylon®) .
  • the composition according to the invention may be manufactured by the known processes generally used in cosmetics.
  • a subject of the invention is also a cosmetic process for caring for, making up or treating human keratin materials and especially human skin, facial lips and integuments, comprising the application of the composition, especially the cosmetic composition as defined above, to the keratin materials.
  • a subject of the invention is also the use of an oil comprising at least two ester functions, in a makeup composition comprising a) at least one liquid fatty phase structured with at least one semi- crystalline polymer having an organic structure, the melting point of which is greater than or equal to 30°C, and b) a dyestuff, the liquid fatty phase, the dyestuff, the polyester oil and the polymer forming a physiologically acceptable medium.
  • a subject of the invention is also the use of a sufficient amount of a polyester oil in a cosmetic composition containing a physiologically acceptable medium comprising a) at least one liquid fatty phase structured with at least one semi-crystalline polymer having an organic structure, the melting point of which is greater than or equal to 30°C, and b) a dyestuff, as an agent for stabilizing the said composition, the said composition depositing a comfortable, glossy film on keratin materials, especially on the lips.
  • a subject of the invention is also the use of a polyester oil in a makeup composition' containing a physiologically acceptable medium comprising at least one liquid fatty phase structured with at least one semi-crystalline polymer having an organic structure, to obtain a stable cosmetic composition.
  • Example 1 Homopolymer with a melting point of 48°C 120 g of Parleam are introduced into a l l reactor equipped with a central paddle stirrer, a condenser and a -thermometer, and are heated from room temperature to 80°C over 45 minutes.
  • the mixture Ci below is introduced over 2 hours : 40 g of cyclohexane + 4 g of Trigonox 141 [2,5- bis (2-ethylhexanoylperoxy) -2 , 5-dimethylhexane] .
  • the mixture C 2 is introduced over 1 hour 30 minutes, this mixture consisting of: 200 g of stearyl acrylate + 400 g of cyclohexane.
  • the mixture is stirred for a further 3 hours at 80°C and all of the cyclohexane present in the reaction medium is then distilled off at atmospheric pressure.
  • the polymer at a concentration of 60% by weight of active material in the Parleam is thus obtained. Its weight-average molecular mass is about 20 000-30 000 and its melting point T m is 48°C, measured by DSC.
  • Example 2 Copolymer with a melting point of 48°C
  • the same procedure as in Example 1 is applied, except that a mixture of 10.g of N- vinylpyrrolidone and 190 g of stearyl acrylate is used.
  • the polymer obtained is at a concentration of 60% by weight of active material in Parleam, its weight-average molecular mass is 43 000-53 000 and its T m is 48°C.
  • Example 3 Homopolymer with a melting point of 58°C
  • Example 4 Copolymer with a melting point of 58°C
  • Example 2 is applied, except that behenyl acrylate is used instead of stearyl acrylate.
  • the polymer obtained is at a concentration of 60% by weight of active material in Parleam®. Its weight-average molecular mass is 23 500- 33 500 and its T m is 58°C.
  • Example 5 Lipstick formulation
  • Octyldecanol 14.5 Diisostearyl malate 9.5 Polyhydroxystearic acid 2 Hydrogenated cocoglycerides 2 Low-melting polymer according to Example 1 11 High-melting polymer according to Example 3 11 Pigments 9 Filler 1 Nacre 3
  • Example 6 Lipstick formulation Low-melting polymer according to Example 1 11% Low-melting polymer according to Example 3 11% Pigments 8.66%
  • This lipstick formulation which contains 14.8% diisostearyl malate, which is a polyester-type oil, is stable for 2 months at 47 °C.
  • This lipstick formulation shows very good heat stability.

Abstract

L'invention concerne une composition de maquillage renfermant a) au moins une phase grasse liquide structurée avec au moins un polymère semi-cristallin doté d'une structure organique, dont le point de fusion est supérieur ou égal à 30 °C, d) un colorant, et c) une huile contenant au moins deux fonctions ester ou « huile polyester », la phase grasse liquide, le colorant, l'huile polyester et le polymère formant un milieu acceptable physiologiquement. Cette composition se présente, notamment, sous la forme d'un bâton qui permet de déposer un film brillant, confortable sur les matières de kératine, notamment sur les lèvres. Cette composition présente l'avantage de posséder une très bonne stabilité thermique.
PCT/EP2003/015019 2002-11-06 2003-11-06 Composition contenant un polymere semi-cristallin et une huile polyester WO2004041150A2 (fr)

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Applications Claiming Priority (4)

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FR0213890 2002-11-06
FR0213890A FR2846552B1 (fr) 2002-11-06 2002-11-06 Composition contenant un polymere semi-cristallin et une huile polyester
US42722802P 2002-11-19 2002-11-19
US60/427,228 2002-11-19

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FR2871053A1 (fr) * 2004-06-08 2005-12-09 Oreal Composition de bonne tenue comprenant des particules de polymere dispersees dans une phase grasse
FR2871055A1 (fr) * 2004-06-08 2005-12-09 Oreal Composition cosmetique comprenant un polymere semi- cristallin et une dispersion de particules de polymere dans une phase grasse
EP1604636A3 (fr) * 2004-06-08 2006-09-20 L'oreal Composition cosmétique comprenant une cire apolaire et une dispersion de particules de polymère dans une phase grasse
WO2007074331A1 (fr) * 2005-12-24 2007-07-05 Croda International Plc Agents de structure pour phases huileuses
DE102009015868A1 (de) 2009-04-01 2009-11-26 Clariant International Limited Kammförmige, kationische Copolymere, deren Herstellung und Verwendung in kosmetischen, pharmazeutischen und dermatologischen Formulierungen
US8142765B2 (en) 2002-01-24 2012-03-27 L'oreal S.A. Composition containing a semi-crystalline polymer and a volatile oil

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US9233063B2 (en) 2009-12-17 2016-01-12 Air Products And Chemicals, Inc. Polymeric compositions for personal care products

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EP1034776A1 (fr) * 1999-03-02 2000-09-13 L'oreal Utilisation dans une composition pour la peau d'un copolymère d'oléfines à cristallisation controlée
EP1262164A1 (fr) * 2001-05-04 2002-12-04 L'oreal Composition à phase grasse liquide gélifiée par un polymère semi-cristallin, contenant une pate particulaire
EP1332753A2 (fr) * 2002-01-24 2003-08-06 L'oreal Composition cosmétique gélifiée par un polymère semi-cristallin

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Publication number Priority date Publication date Assignee Title
EP1034776A1 (fr) * 1999-03-02 2000-09-13 L'oreal Utilisation dans une composition pour la peau d'un copolymère d'oléfines à cristallisation controlée
EP1262164A1 (fr) * 2001-05-04 2002-12-04 L'oreal Composition à phase grasse liquide gélifiée par un polymère semi-cristallin, contenant une pate particulaire
EP1332753A2 (fr) * 2002-01-24 2003-08-06 L'oreal Composition cosmétique gélifiée par un polymère semi-cristallin

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8142765B2 (en) 2002-01-24 2012-03-27 L'oreal S.A. Composition containing a semi-crystalline polymer and a volatile oil
FR2871053A1 (fr) * 2004-06-08 2005-12-09 Oreal Composition de bonne tenue comprenant des particules de polymere dispersees dans une phase grasse
FR2871055A1 (fr) * 2004-06-08 2005-12-09 Oreal Composition cosmetique comprenant un polymere semi- cristallin et une dispersion de particules de polymere dans une phase grasse
EP1604633A2 (fr) * 2004-06-08 2005-12-14 L'oreal Composition de bonne tenue comprenant des particules de polymère dispersées dans une phase grasse
EP1604637A2 (fr) * 2004-06-08 2005-12-14 L'oreal Composition cosmétique comprenant un polymère semi-cristallin et une dispersion de particules de polymère dans une phase grasse
EP1604636A3 (fr) * 2004-06-08 2006-09-20 L'oreal Composition cosmétique comprenant une cire apolaire et une dispersion de particules de polymère dans une phase grasse
EP1604637A3 (fr) * 2004-06-08 2006-09-20 L'oreal Composition cosmétique comprenant un polymère semi-cristallin et une dispersion de particules de polymère dans une phase grasse
EP1604633A3 (fr) * 2004-06-08 2006-09-20 L'oreal Composition de bonne tenue comprenant des particules de polymère dispersées dans une phase grasse
WO2007074331A1 (fr) * 2005-12-24 2007-07-05 Croda International Plc Agents de structure pour phases huileuses
US9023329B2 (en) 2005-12-24 2015-05-05 Croda International, Plc Structurants for oil phases
DE102009015868A1 (de) 2009-04-01 2009-11-26 Clariant International Limited Kammförmige, kationische Copolymere, deren Herstellung und Verwendung in kosmetischen, pharmazeutischen und dermatologischen Formulierungen
WO2010112185A1 (fr) 2009-04-01 2010-10-07 Clariant International Ltd Copolymères cationiques en peigne, leur production et leur utilisation dans des formulations cosmétiques, pharmaceutiques et dermatologiques

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