US20060134032A1 - Nail varnish composition comprising a sequenced polymer - Google Patents

Nail varnish composition comprising a sequenced polymer Download PDF

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US20060134032A1
US20060134032A1 US10528699 US52869905A US2006134032A1 US 20060134032 A1 US20060134032 A1 US 20060134032A1 US 10528699 US10528699 US 10528699 US 52869905 A US52869905 A US 52869905A US 2006134032 A1 US2006134032 A1 US 2006134032A1
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characterized
equal
composition according
block
monomers
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US10528699
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Philippe Ilekti
Bertrand Lion
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L'Oreal SA
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L'Oreal SA
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    • 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
    • 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
    • A61K8/19Cosmetics or similar toilet preparations characterised by the composition containing inorganic ingredients
    • A61K8/26Aluminium; Compounds thereof
    • 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
    • A61K8/81Cosmetics or similar toilet preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • A61K8/8105Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
    • A61K8/8111Homopolymers or copolymers of aliphatic olefines, e.g. polyethylene, polyisobutene; Compositions of derivatives of such polymers
    • 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
    • A61K8/81Cosmetics or similar toilet preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • A61K8/8141Compositions 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
    • A61K8/8152Homopolymers or copolymers of esters, e.g. (meth)acrylic acid esters; Compositions of derivatives of such polymers
    • 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
    • A61K8/81Cosmetics or similar toilet preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • A61K8/817Compositions 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)
    • A61K8/8182Copolymers of vinyl-pyrrolidones. Compositions of derivatives of such polymers
    • 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
    • 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
    • A61K8/90Block copolymers
    • 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
    • A61K8/92Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof
    • A61K8/922Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof of vegetable origin
    • 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
    • A61K8/92Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof
    • A61K8/927Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof of insects, e.g. shellac
    • 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
    • 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
    • A61Q1/10Preparations 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
    • A61Q3/00Manicure or pedicure preparations
    • A61Q3/02Nail coatings
    • 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
    • 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
    • C08F265/06Polymerisation of acrylate or methacrylate esters on to polymers thereof
    • 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
    • C08F291/00Macromolecular compounds obtained by polymerising monomers on to macromolecular compounds according to more than one of the groups C08F251/00 - C08F289/00
    • 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
    • C08F293/00Macromolecular compounds obtained by polymerisation on to a macromolecule having groups capable of inducing the formation of new polymer chains bound exclusively at one or both ends of the starting macromolecule
    • C08F293/005Macromolecular compounds obtained by polymerisation on to a macromolecule having groups capable of inducing the formation of new polymer chains bound exclusively at one or both ends of the starting macromolecule using free radical "living" or "controlled" polymerisation, e.g. using a complexing agent
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08LCOMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L53/00Compositions of block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES
    • A61K2800/00Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/59Mixtures
    • A61K2800/594Mixtures of polymers
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10STECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S514/00Drug, bio-affecting and body treating compositions
    • Y10S514/844Cosmetic, facial
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10STECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S514/00Drug, bio-affecting and body treating compositions
    • Y10S514/844Cosmetic, facial
    • Y10S514/845Liquid make-up
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10STECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S514/00Drug, bio-affecting and body treating compositions
    • Y10S514/937Dispersion or emulsion

Abstract

The present invention relates to a nail varnish composition comprising, in a cosmetically acceptable medium, at least one particular block polymer, the said composition being free of nitrocellulose and having a mean gloss greater than 50 out of 100. A subject of the invention is also the use of such a composition to obtain a film, deposited on the nails, which is glossy and which shows good staying power and wear resistance.

Description

  • The present invention relates to a nail varnish free from nitrocellulose comprising a block polymer. The invention also relates to a makeup or care process for the nails. These compositions may be applied to human nails or to false nails.
  • The compositions to be applied to the nails, of the type such as solvent-based nail varnishes or nailcare bases, usually comprise at least one film-forming polymer, optionally plasticizer, pigments, rheological agents and solvents.
  • Nitrocellulose is a film-forming agent commonly used in solvent-based nail varnishes to obtain glossy compositions with good strength.
  • Nitrocellulose is a polymer consisting of an assembly of partially nitrated anhydroglucose rings obtained by esterification of some of the free hydroxyl functions of a cellulose with nitric acid in the presence of sulfuric acid.
  • At the present time, nitrocellulose is still the main film-forming agent the most widely used in solvent-based nail varnishes in formulations with optimized gloss and strength.
  • However, formulations comprising nitrocelluloses have the following drawbacks:
      • they make it possible to obtain films with satisfactory levels of hardness and gloss, but with unsatisfactory strength over time, especially due to the poor chip strength of the film;
      • they give hard films that lack adhesion to the nail.
        This drawback may be overcome by adding plasticizers, but, in this case, very large amounts of plasticizers and of co-resins, of the order of that of nitrocellulose, need to be used. Furthermore, the presence of plasticizers in these formulations is reflected, after film formation and drying, especially by a change in the properties of the film over time, due both to slow evaporation of the residual solvents contained in the film after drying, and to a potential loss of some of the plasticizers, especially by evaporation, resulting in hardening of the film over time and poor chip strength.
  • Certain known formulations comprising nitrocellulose have the drawback of yellowing on the nail over time. In addition, the manufacture of nitrocellulose, its transportation and its incorporation into formulations pose safety problems which are such that it is sought to replace it with other film-forming agents.
  • The studies conducted with regard to the replacement of nitrocellulose with other film-forming agents such as polyacrylics and polyurethanes in nail varnishes, for instance the aqueous polyurethane dispersions described in document EP 0 648 485, have not given satisfactory results, especially in terms of strength and resistance to external factors such as water or detergents.
  • Patent application US 2002/18759 describes an acrylic acid/butyl methacrylate copolymer as film-forming polymer for partially replacing nitrocellulose. Nail varnishes containing this polymer do not show sufficient strength and in particular sufficient gloss strength, and require the addition of plasticizers.
  • The Applicant has discovered a novel route for formulating a nitrocellulose-free nail varnish that has good gloss and strength properties.
  • This nail varnish also makes it possible to obtain plasticization of films without the need to add large amounts of external plasticizers, while at the same time maintaining a good level of hardness of the films and good impact strength and/or chip strength of the varnishes on the nail, and thus an improvement in the strength over time of the varnishes on the nail and/or in their wear resistance.
  • One subject of the invention is, more specifically, a nail varnish composition comprising, in a cosmetically acceptable organic solvent, at least one linear ethylenic film-forming block polymer, the said composition being free of nitrocellulose, the block polymer being such that, when it is present in sufficient amount in the composition, the mean gloss at 20° of a deposit of the said composition, once spread onto a support, is greater than or equal to 50 out of 100.
  • A subject of the invention is also a nail varnish composition comprising, in a cosmetically acceptable medium, at least one linear block ethylenic film-forming polymer as described below, the said composition being free of nitrocellulose.
  • The term “nitrocellulose” means any nitrated cellulose derivative, in particular nitrocellulose.
  • According to the present invention, the term “film-forming polymer” means a polymer that is capable of forming, by itself or in the presence of an auxiliary film-forming agent, a continuous film that adheres to a support, and especially to keratin materials.
  • The term “nitrocellulose-free composition” means a composition containing less than 5%, preferably less than 3%, preferably less than 2%, preferably less than 1%, preferably less than 0.5%, preferably less than 0.1% and preferably less than 0.05% of nitrocellulose.
  • A subject of the invention is also a non-therapeutic cosmetic process for making up or caring for the nails, comprising the application to the nails of at least one coat of the nail varnish composition as defined above.
  • A subject of the invention is also a nail varnish composition comprising at least one film-forming linear ethylenic block polymer, the said composition being free of nitrocellulose, to obtain a film, once spread onto a support, which has a gloss at 200 of greater than 50 out of 100, and which incidentally has good strength.
  • Mean Gloss of the Composition
  • The term “mean gloss” means the gloss as may be conventionally measured using a glossmeter by the following method.
  • A coat of between 50 μm and 150 μm in thickness of the composition is spread using an automatic spreader onto a Leneta brand contrast card of reference Form 1A Penopac. The coat covers at least the white background of the card. The deposit is left to dry for 24 hours at a temperature of 30° C., and the gloss at 20° is then measured on the white background using a Byk Gardner brand glossmeter of reference microTri-Gloss.
  • This measurement (between 0 and 100) is repeated at least three times, and the mean gloss is the mean of the at least three measurements taken.
  • The mean gloss of the composition measured at 20° is advantageously greater than or equal to 50 out of 100, better still greater than or equal to 55, even better still greater than or equal to 60, even better still greater than or equal to 65, even better still greater than or equal to 70 or even better still greater than or equal to 75 out of 100, or even greater than or equal to 80 out of 100.
  • Preferably, the mean gloss of the composition, once spread onto a support, measured at 60° is greater than or equal to 50, better still greater than or equal to 60, better still greater than or equal to 65, better still greater than or equal to 70, better still greater than or equal to 75, better still greater than or equal to 80, better still greater than or equal to 85 or better still greater than or equal to 90 out of 100.
  • The mean gloss at 60° is measured as follows. The gloss may be conventially measured using a glossmeter by the following method.
  • A coat of between 50 μm and 150 μm in thickness of the composition is spread using an automatic spreader onto a Leneta brand contrast card of reference Form 1A Penopac. The coat covers at least the white background of the card. The deposit is left to dry for 24 hours at a temperature of 30° C., and the gloss at 60° is then measured on the white background using a Byk Gardner brand glossmeter of reference microTri-Gloss.
  • This measurement (between 0 and 100) is repeated at least three times, and the mean gloss is the mean of the at least three measurements taken.
  • According to one embodiment, the gloss of the composition measured at 20° is preferably greater than or equal to 60, preferably 65, 70 or 75 out of 100, and/or the gloss of the composition measured at 60° is preferably greater than or equal to 80, 85 or 90 out of 100.
  • Block Polymer:
  • The composition according to the present invention contains at least one block polymer. The term “block polymer” means a polymer comprising at least two different blocks and preferably at least three different blocks.
  • According to one embodiment, the block polymer of the composition according to the invention is an ethylenic polymer. The term “ethylenic polymer” means a polymer obtained by polymerization of ethylenically unsaturated monomers.
  • According to one embodiment, the block polymer of the composition according to the invention is a linear polymer. In contrast, a polymer of non-linear structure is, for example, a polymer of branched, starburst or grafted structure, or the like.
  • According to one embodiment, the block polymer of the composition according to the invention is a film-forming polymer. The term “film-forming polymer” means a polymer that is capable of forming, by itself or in the presence of an auxiliary film-forming agent, a continuous film that adheres to a support and especially to keratin materials.
  • According to one embodiment, the block polymer of the composition according to the invention is a non-elastomeric polymer.
  • The term “non-elastomeric polymer” means a polymer which, when subjected to a stress intended to stretch it (for example by 30% relative to its initial length), does not return to a length substantially identical to its initial length when the stress is removed.
  • More specifically, the expression “non-elastomeric polymer” means a polymer with an instantaneous recovery Ri<50% and a delayed recovery R2h<70% after having undergone a 30% elongation. Preferably, Ri is <30%, and R2h<50%.
  • More specifically, the non-elastomeric nature of the polymer is determined according to the following protocol:
  • A polymer film is prepared by pouring a solution of the polymer into a Teflon-coated mould followed by drying for 7 days under ambient conditions regulated to 23±5° C. and 50±10% relative humidity.
  • A film about 100 μm thick is thus obtained, from which are cut rectangular specimens (for example using a punch) 15 mm wide and 80 mm long.
  • This sample is subjected to a tensile stress using a machine sold under the reference Zwick, under the same temperature and humidity conditions as for the drying operation.
  • The specimens are drawn at a speed of 50 mm/minute and the distance between the jaws is 50 mm, which corresponds to the initial length (l0) of the specimen.
  • The instantaneous recovery Ri is determined in the following manner:
      • the specimen is stretched by 30% (εmax), i.e. about 0.3 times its initial length (l0)
      • the stress is released by applying a return speed equal to the tensile speed, i.e. 50 mm/minute, and the residual percentage elongation of the specimen, after returning to zero load (εi), is measured.
  • The percentage instantaneous recovery (Ri) is given by the formula below:
    R i=((εmax−εi)/εmax)×100
  • To determine the delayed recovery, the residual elongation of the sample is measured as a percentage (ε2h), 2 hours after returning to zero stress.
  • The percentage delayed recovery (R2h) is given by the formula below:
    R 2h=((εmax−ε2h)/εmax)×100
  • Purely by way of indication, a polymer according to an embodiment of the invention has an instantaneous recovery Ri of 10% and a delayed recovery R2h of 30%.
  • According to another embodiment, the block polymer of the composition according to the invention does not comprise any styrene units. The expression “polymer free of styrene units” means a polymer comprising less than 10%, preferably less than 5%, preferentially less than 2% and more preferentially less than 1% by weight i) of styrene units of formula —CH(C6H5)—CH2— or ii) of substituted styrene units, for instance methylstyrene, chlorostyrene or chloromethylstyrene.
  • According to one embodiment, the block polymer of the composition according to the invention is derived from aliphatic ethylenic monomers. The term “aliphatic monomer” means a monomer comprising no aromatic groups.
  • According to one embodiment, the block polymer is an ethylenic polymer derived from aliphatic ethylenic monomers comprising a carbon-carbon double bond and at least one ester group —COO— or amide group —CON—. The ester group may be linked to one of the two unsaturated carbons via the carbon atom or the oxygen atom. The amide group may be linked to one of the two unsaturated carbons via the carbon atom or the nitrogen atom.
  • According to one embodiment, the block polymer comprises at least one first block and at least one second block.
  • The term “at least one block” means one or more blocks.
  • It is pointed out that, in the text hereinabove and hereinbelow, the terms “first” and “second” blocks do not in any way condition the order of the said blocks in the polymer structure.
  • According to one embodiment, the block polymer comprises at least one first block and at least one second block that have different glass transition temperatures (Tg).
  • In this embodiment, the first and second blocks may be linked together via an intermediate segment with a glass transition temperature between the glass transition temperatures of the first and second blocks.
  • According to one embodiment, the block polymer comprises at least one first block and at least one second block linked together via an intermediate segment comprising at least one constituent monomer of the first block and at least one constituent monomer of the second block.
  • Preferably, the intermediate block is derived essentially from constituent monomers of the first block and of the second block.
  • The term “essentially” means at least 85%, preferably at least 90%, better still 95% and even better still 100%.
  • Advantageously, the intermediate segment comprising at least one constituent monomer of the first block and at least one constituent monomer of the second block of the polymer is a random polymer.
  • According to one embodiment, the block polymer comprises at least one first block and at least one second block that are incompatible in the organic liquid medium of the composition of the invention.
  • The term “mutually incompatible blocks” means that the mixture formed from the polymer corresponding to the first block and from the polymer corresponding to the second block is not miscible in the organic liquid that is in major amount by weight contained in the organic liquid medium of the composition, at room temperature (25° C.) and atmospheric pressure (105 Pa), for a content of the polymer mixture of greater than or equal to 5% by weight, relative to the total weight of the mixture (polymers and major organic liquid), it being understood that:
  • i) the said polymers are present in the mixture in a content such that the respective weight ratio ranges from 10/90 to 90/10, and
  • ii) each of the polymers corresponding to the first and second blocks has an average (weight-average or number-average) molecular mass equal to that of the block polymer ±15%.
  • When the organic liquid medium comprises a mixture of organic liquids, in the case of two or more liquids present in identical mass proportions, the said polymer mixture is immiscible in at least one of them.
  • When the organic liquid medium comprises only one organic liquid, this liquid obviously constitutes the liquid that is in major amount by weight.
  • The term “organic liquid medium” means a medium containing at least one organic liquid, i.e. at least one organic compound that is liquid at room temperature (25° C.) and atmospheric pressure (105 Pa) According to one embodiment, the major liquid of the organic liquid medium is a volatile or non-volatile oil (fatty substance). Preferably, the organic liquid is cosmetically acceptable (acceptable tolerance, toxicology and feel). The organic liquid medium is cosmetically acceptable, in the sense that it is compatible with keratin materials, for instance the oils or organic solvents commonly used in cosmetic compositions.
  • According to one embodiment, the major liquid of the organic liquid medium is the polymerization solvent or one of the polymerization solvents of the block polymer, as are described below.
  • The term “polymerization solvent” means a solvent or a mixture of solvents. The polymerization solvent may be chosen especially from ethyl acetate, butyl acetate, alcohols such as isopropanol and ethanol, aliphatic alkanes such as isododecane, and mixtures thereof. Preferably, the polymerization solvent is a mixture of butyl acetate and isopropanol, or isododecane.
  • In general, the block polymer may be incorporated into the composition to a high solids content, typically greater than 10%, greater than 20%, more preferably greater than 30% and more preferentially greater than 45% by weight relative to the total weight of the composition, while at the same time being easy to formulate.
  • Preferably, the block polymer comprises no silicon atoms in its skeleton. The term “skeleton” means the main chain of the polymer, as opposed to the pendent side chains.
  • Preferably, the polymer according to the invention is not water-soluble, i.e. the polymer is not soluble in water or in a mixture of water and linear or branched lower monoalcohols containing from 2 to 5 carbon atoms, for instance ethanol, isopropanol or n-propanol, without pH modification, at an active material content of at least 1% by weight, at room temperature (25° C.).
  • According to one embodiment, the block polymer has a polydispersity index I of greater than 2.
  • Advantageously, the block polymer used in the. compoisitions according to the invention has a polydispersity index greater than 2, for example ranging from 2 to 9, preferably greater than or equal to 2.5, for example ranging from 2.5 to 8 and better still greater than or equal to 2.8 and especially ranging from 2.8 to 6.
  • The polydispersity index I of the polymer is equal to the ratio of the weight-average mass Mw to the number-average mass Mn.
  • The weight-average molar mass (Mw) and number-average molar mass (Mn) are determined by gel permeation liquid chromatography (THF solvent, calibration curve established with linear polystyrene standards, refractometric detector).
  • The weight-average mass (Mw) of the block polymer is preferably less than or equal to 300 000; it ranges, for example, from 35 000 to 200 000 and better still from 45 000 to 150 000.
  • The number-average mass (Mn) of the block polymer is preferably less than or equal to 70 000; it ranges, for example, from 10 000 to 60 000 and better still from 12 000 to 50 000.
  • Each block of the block polymer is derived from one type of monomer or from several different types of monomer.
  • This means that each block may consist of a homopolymer or a copolymer; this copolymer constituting the block may in turn be random or alternating.
  • The glass transition temperatures indicated for the first and second blocks may be theoretical Tg values determined from the theoretical Tg values of the constituent monomers of each of the blocks, which may be found in a reference manual such as the Polymer Handbook, 3rd Edition, 1989, John Wiley, according to the following relationship, known as Fox's law: 1 / Tg = i ( ϖ i / Tg i ) ,
    {overscore (ω)} being the mass fraction of the monomer i in the block under consideration and Tgi being the glass transition temperature of the homopolymer of the monomer i.
  • Unless otherwise indicated, the Tg values indicated for the first and second blocks in the present patent application are theoretical Tg values.
  • The difference between the glass transition temperatures of the first and second blocks is generally greater than 10° C., preferably greater than 20° C. and better still greater than 30° C.
  • In particular, the block polymer comprises at least one first block and at least one second block such that the first block may be chosen from:
  • a) a block with a Tg of greater than or equal to 40° C.,
  • b) a block with a Tg of less than or equal to 20° C.,
  • c) a block with a Tg of between 20 and 40° C., and the second block may be chosen from a category a), b) or c) that is different from the first block.
  • In the present invention, the expression: “between . . . and . . . ” is intended to denote a range of values for which the limits mentioned are excluded, and “from . . . to . . . ” and “ranging from . . . to . . . ” are intended to denote a range of values for which the limits are included.
  • a) Block With a Tg of Greater Than or Equal to 40° C.
  • The block with a Tg of greater than or equal to 40° C. has, for example, a Tg ranging from 40 to 150° C., preferably greater than or equal to 50° C., for example ranging from 50° C. to 120° C. and better still greater than or equal to 60° C., for example ranging from 60° C. to 120° C.
  • The block with a Tg of greater than or equal to 40° C. may be a homopolymer or a copolymer.
  • The block with a Tg of greater than or equal to 40° C. may be totally or partially derived from one or more monomers which are such that the homopolymer prepared from these monomers has a glass transition temperature of greater than or equal to 40° C.
  • In the case where this block is a homopolymer, it is derived from monomers which are such that the homopolymers prepared from these monomers have glass transition temperatures of greater than or equal to 40° C. This first block may be a homopolymer consisting of only one type of monomer (for which the Tg of the corresponding homopolymer is greater than or equal to 40° C.).
  • In the case where the first block is a copolymer, it may be totally or partially derived from one or more monomers, the nature and concentration of which are chosen such that the Tg of the resulting copolymer is greater than or equal to 40° C. The copolymer may comprise, for example:
      • monomers which are such that the homopolymers prepared from these monomers have Tg values of greater than or equal to 40° C., for example a Tg ranging from 40 to 150° C., preferably greater than or equal to 50° C., for example ranging from 50° C. to 120° C. and better still greater than or equal to 60° C., for example ranging from 60° C. to 120° C., and
      • monomers which are such that the homopolymers prepared from these monomers have Tg values of less than 40° C., chosen from monomers with a Tg of between 20 and 40° C. and/or monomers with a Tg of less than or equal to 20° C., for example a Tg ranging from −100 to 20° C., preferably less than 15° C., especially ranging from −80° C. to 15° C. and better still less than 10° C., for example ranging from −50° C. to 0° C., as described later.
  • The monomers whose homopolymers have a glass transition temperature of greater than or equal to 40° C. are chosen, for example, from the following monomers, also known as the main monomers:
      • methacrylates of formula CH2═C(CH3)—COOR1 in which R1 represents a linear or branched unsubstituted alkyl group containing from 1 to 4 carbon atoms, such as a methyl, ethyl, propyl or isobutyl group or R1 represents a C4 to C12 cycloalkyl group,
      • acrylates of formula CH2═CH—COOR2 in which R2 represents a C4 to C12 cycloalkyl group such as isobornyl acrylate or a tert-butyl group,
      • (meth)acrylamides of formula:
        Figure US20060134032A1-20060622-C00001

        in which R7 and R8, which may be identical or different, each represent a hydrogen atom or a linear or branched C1 to C12 alkyl group such as an n-butyl, t-butyl, isopropyl, isohexyl, isooctyl or isononyl group; or R7 represents H and R8 represents a 1,1-dimethyl-3-oxobutyl group, and R′ denotes H or methyl. Examples of monomers that may be mentioned include N-butylacrylamide, N-t-butylacrylamide, N-isopropylacrylamide, N,N-dimethylacrylamide and N,N-dibutylacrylamide,
      • and mixtures thereof.
  • Main monomers that are particularly preferred are methyl methacrylate, isobutyl (meth)acrylate and isobornyl (meth)acrylate, and mixtures thereof.
  • b) Block with a Tg of Less Than or Equal to 20° C.
  • The block with a Tg of less than or equal to 20° C. has, for example, a Tg ranging from −100 to 20° C., preferably less than or equal to 15° C., especially ranging from −80° C. to 15° C. and better still less than or equal to 10° C., for example ranging from −50° C. to 0° C.
  • The block with a Tg of less than or equal to 20° C. may be a homopolymer or a copolymer.
  • The block with a Tg of less than or equal to 20° C. may be totally or partially derived from one or more monomers which are such that the homopolymer prepared from these monomers has a glass transition temperature of less than or equal to 20° C.
  • In the case where this block is a homopolymer, it is derived from monomers which are such that the homopolymers prepared from these monomers have glass transition temperatures of less than or equal to 20° C. This second block may be a homopolymer consisting of only one type of monomer (for which the Tg of the corresponding homopolymer is less than or equal to 20° C.).
  • In the case where the block with a Tg of less than or equal to 20° C. is a copolymer, it may be totally or partially derived from one or more monomers, the nature and concentration of which are chosen such that the Tg of the resulting copolymer is less than or equal to 20° C.
  • It may comprise, for example
      • one or more monomers whose corresponding homopolymer has a Tg of less than or equal to 20° C., for example a Tg ranging from −100° C. to 20° C., preferably less than 15° C., especially ranging from −80° C. to 15° C. and better still less than 10° C., for example ranging from −50° C. to 0° C., and
      • one or more monomers whose corresponding homopolymer has a Tg of greater than 20° C., such as monomers with a Tg of greater than or equal to 40° C., for example a Tg ranging from 40 to 150° C., preferably greater than or equal to 50° C., for example ranging from 50° C. to 120° C. and better still greater than or equal to 60° C., for example ranging from 60° C. to 120° C. and/or monomers with a Tg of between 20 and 40° C., as described above.
  • Preferably, the block with a Tg of less than or equal to 20° C. is a homopolymer.
  • The monomers whose homopolymer has a Tg of less than or equal to 20° C. are preferably chosen from the following monomers, or main monomer:
      • acrylates of formula CH2═CHCOOR3,
        R3 representing a linear or branched C1 to C12 unsubstituted alkyl group, with the exception of the tert-butyl group, in which one or more hetero atoms chosen from O, N and S is (are) optionally intercalated,
      • methacrylates of formula CH2═C(CH3)—COOR4,
        R4 representing a linear or branched C6 to C12 unsubstituted alkyl group, in which one or more hetero atoms chosen from O, N and S is (are) optionally intercalated,
      • vinyl esters of formula R5—CO—O—CH═CH2
        in which R5 represents a linear or branched C4 to C12 alkyl group,
      • C4 to C12 alkyl vinyl ethers,
      • N-(C4 to C12)alkyl acrylamides; such as N-octylacrylamide,
      • and mixtures thereof.
  • The main monomers that are particularly preferred for the block with a Tg of less than or equal to 20° C. are alkyl acrylates whose alkyl chain contains from 1 to 10 carbon atoms, with the exception of the tert-butyl group, such as methyl acrylate, isobutyl acrylate and 2-ethylhexyl acrylate, and mixtures thereof.
  • c) Block With a Tg of Between 20 and 40° C.
  • The block with a Tg of between 20 and 40° C. may be a homopolymer or a copolymer.
  • The block with a Tg of between 20 and 40° C. may be totally or partially derived from one or more monomers which are such that the homopolymer prepared from these monomers has a glass transition temperature of between 20 and 40° C.
  • The block with a Tg of between 20 and 40° C. may be totally or partially derived from monomers which are such that the corresponding homopolymer has a Tg of greater than or equal to 40° C., and from monomers which are such that the corresponding homopolymer has a Tg of less than or equal to 20° C.
  • In the case where this block is a homopolymer, it is derived from monomers (or main monomer) which are such that the homopolymers prepared from these monomers have glass transition temperatures of between 20 and 40° C. This first block may be a homopolymer, consisting of only one type of monomer (for which the Tg of the corresponding homopolymer ranges from 20° C. to 40° C.).
  • The monomers whose homopolymer has a glass transition temperature of between 20 and 40° C. are preferably chosen from n-butyl methacrylate, cyclodecyl acrylate, neopentyl acrylate and isodecylacrylamide, and mixtures thereof.
  • In the case where the block with a Tg of between 20 and 40° C. is a copolymer, it is totally or partially derived from one or more monomers (or main monomer) whose nature and concentration are chosen such that the Tg of the resulting copolymer is between 20 and 40° C.
  • Advantageously, the block with a Tg of between 20 and 40° C. is a copolymer totally or partially derived from:
      • main monomers whose corresponding homopolymer has a Tg of greater than or equal to 40° C., for example a Tg ranging from 40° C. to 150° C., preferably greater than or equal to 50° C., for example ranging from 50 to 120° C. and better still greater than or equal to 60° C., for example ranging from 60° C. to 120° C., as described above, and/or
      • main monomers whose corresponding homopolymer has a Tg of less than or equal to 20° C., for example a Tg ranging from −100 to 20° C., preferably less than or equal to 15° C., especially ranging from −80° C. to 15° C. and better still less than or equal to 10° C., for example ranging from −50° C. to 0° C., as described above, the said monomers being chosen such that the Tg of the copolymer forming the first block is between 20 and 40° C.
  • Such main monomers are chosen, for example, from methyl methacrylate, isobornyl acrylate and methacrylate, butyl acrylate and 2-ethylhexyl acrylate, and mixtures thereof.
  • Preferably, the proportion of the second block with a Tg of less than or equal to 20° C. ranges from 10% to 85% by weight, better still from 20% to 70% and even better still from 20% to 50% by weight of the polymer.
  • Preferably, each of the first and second blocks comprises at least one monomer chosen from acrylic acid, acrylic acid esters, (meth)acrylic acid and (meth)acrylic acid esters, and mixtures thereof.
  • Advantageously, each of the first and second blocks is totally derived from at least one monomer chosen from acrylic acid, acrylic acid esters, (meth)acrylic acid and (meth)acrylic acid esters, and mixtures thereof.
  • However, each of the blocks may contain in small proportion at least one constituent monomer of the other block.
  • Thus, the first block may contain at least one constituent monomer of the second block, and vice versa.
  • Each of the first and/or second blocks may comprise, in addition to the monomers indicated above, one or more other monomers known as additional monomers, which are different from the main monomers mentioned above.
  • The nature and amount of this or these additional monomer(s) are chosen such that the block in which they are present has the desired glass transition temperature.
  • This additional monomer is chosen, for example, from:
  • hydrophilic monomers such as:
      • ethylenically unsaturated monomers comprising at least one carboxylic or sulphonic acid function, for instance:
  • acrylic acid, methacrylic acid, crotonic acid, maleic anhydride, itaconic acid, fumaric acid, maleic acid, acrylamidopropanesulphonic acid, vinylbenzoic acid, vinylphosphoric acid, and salts thereof,
      • ethylenically unsaturated monomers comprising at least one tertiary amine function, for instance 2-vinylpyridine, 4-vinylpyridine, dimethylaminoethyl methacrylate, diethylaminoethyl methacrylate and dimethylaminopropylmethacrylamide, and salts thereof,
      • methacrylates of formula CH2═C(CH3)—COOR6
  • in which R6 represents a linear or branched alkyl group containing from 1 to 4 carbon atoms, such as a methyl, ethyl, propyl or isobutyl group, the said alkyl group being substituted with one or more substituents chosen from hydroxyl groups (for instance 2-hydroxypropyl methacrylate and 2-hydroxyethyl methacrylate) and halogen atoms (Cl, Br, I or F), such as trifluoroethyl methacrylate,
      • methacrylates of formula CH2═C(CH3)—COOR9,
  • R9 representing a linear or branched C6 to C12 alkyl group in which one or more hetero atoms chosen from O, N and S is (are) optionally intercalated, the said alkyl group being substituted with one or more substituents chosen from hydroxyl groups and halogen atoms (Cl, Br, I or F);
      • acrylates of formula CH2═CHCOOR10,
  • R10 representing a linear or branched C1 to C12 alkyl group substituted with one or more substituents chosen from hydroxyl and halogen atoms (Cl, Br, I or F), such as 2-hydroxypropyl acrylate and 2-hydroxyethyl acrylate, or R10 represents a (C1-C12) alkyl-O-POE (polyoxyethylene) with repetition of the oxyethylene unit 5 to 30 times, for example methoxy-POE, or R10 represents a polyoxyethylenated group comprising from 5 to 30 ethylene oxide units
  • b) ethylenically unsaturated monomers comprising one or more silicon atoms, such as methacryloxypropyltrimethoxysilane and methacryloxypropyltris(trimethylsiloxy)silane,
      • and mixtures thereof.
  • Additional monomers that are particularly preferred are acrylic acid, methacrylic acid and trifluoroethyl methacrylate, and mixtures thereof.
  • According to one embodiment, each of the first and second blocks of the block polymer comprises at least one monomer chosen from (meth)acrylic acid esters and optionally at least one additional monomer such as (meth)acrylic acid, and mixtures thereof.
  • According to another embodiment, each of the first and second blocks of the block polymer is totally derived from at least one monomer chosen from (meth)acrylic acid esters and optionally from at least one additional monomer such as (meth)acrylic acid, and mixtures thereof.
  • According to one preferred embodiment, the block polymer is a non-silicone polymer, i.e. a polymer free of silicon atoms.
  • This or these additional monomer(s) generally represent(s) an amount of less than or equal to 30% by weight, for example from 1% to 30% by weight, preferably from 5% to 20% by weight and more preferably from 7% to 15% by weight, relative to the total weight of the first and/or second blocks.
  • The block polymer may be obtained by free-radical solution polymerization according to the following preparation process:
      • a portion of the polymerization solvent is introduced into a suitable reactor and heated until the adequate temperature for the polymerization is reached (typically between 60 and 120° C.),
      • once this temperature is reached, the constituent monomers of the first block are introduced in the presence of some of the polymerization initiator, after a time T corresponding to a maximum degree of conversion of 90%, the constituent monomers of the second block and the rest of the initiator are introduced,
      • the mixture is left to react for a time {dot over (T)}′ (ranging from 3 to 6 hours), after which the mixture is cooled to room temperature,
        • the polymer dissolved in the polymerization solvent is obtained.
    FIRST EMBODIMENT
  • According to a first embodiment, the block polymer comprises a first block with a Tg of greater than or equal to 40° C., as described above in a) and a second block with a Tg of less than or equal to 20° C., as described above in b).
  • Preferably, the first block with a Tg of greater than or equal to 40° C. is a copolymer derived from monomers which are such that the homopolymer prepared from these monomers has a glass transition temperature of greater than or equal to 40° C., such as the monomers described above.
  • Advantageously, the second block with a Tg of less than or equal to 20° C. is a homopolymer derived from monomers which are such that the homopolymer prepared from these monomers has a glass transition temperature of less than or equal to 20° C., such as the monomers described above.
  • Preferably, the proportion of the block with a Tg of greater than or equal to 40° C. ranges from 20% to 90%, better still from 30% to 80% and even better still from 50% to 70% by weight of the polymer. Preferably, the proportion of the block with a Tg of less than or equal to 20° C. ranges from 5% to 75%, preferably from 15% to 50% and better still from 25% to 45% by weight of the polymer.
  • Thus, according to a first variant, the polymer according to the invention may comprise:
      • a first block with a Tg of greater than or equal to 40° C., for example having a Tg ranging from 70 to 110° C., which is a methyl methacrylate/acrylic acid copolymer,
      • a second block with a Tg of less than or equal to 20° C., for example ranging from 0 to 20° C., which is a methyl acrylate homopolymer, and
      • an intermediate block which is a methyl
        methacrylate/acrylic acid/methyl acrylate copolymer.
  • According to a second variant, the polymer according to the invention may comprise:
      • a first block with a Tg of greater than or equal to 40° C., for example ranging from 70 to 100° C., which is a methyl methacrylate/acrylic acid/trifluoroethyl methacrylate copolymer,
      • a second block with a Tg of less than or equal to 20° C., for example ranging from 0 to 20° C., which is a methyl acrylate homopolymer, and
      • an intermediate block which is a methyl methacrylate/acrylic acid/methyl acrylate/trifluoroethyl methacrylate random copolymer.
  • According to a third variant, the polymer according to the invention may comprise:
      • a first block with a Tg of greater than or equal to 40° C., for example ranging from 85 to 115° C., which is an isobornyl acrylate/isobutyl methacrylate copolymer,
      • a second block with a Tg of less than or equal to 20° C., for example ranging from −85 to −55° C., which is a 2-ethylhexyl acrylate homopolymer, and
      • an intermediate block, which is an isobornyl acrylate/isobutyl methacrylate/2-ethylhexyl acrylate random copolymer.
  • According to a fourth variant, the polymer according to the invention may comprise:
      • a first block with a Tg of greater than or equal to 40° C., for example ranging from 85 to 115° C., which is an isobornyl acrylate/methyl methacrylate copolymer,
      • a second block with a Tg of less than or equal to 20° C., for example ranging from −85 to −55° C., which is a 2-ethylhexyl acrylate homopolymer, and
      • an intermediate block which is an isobornyl acrylate/methyl methacrylate/2-ethylhexyl acrylate. random copolymer.
  • According to a fifth variant, the polymer according to the invention may comprise:
      • a first block with a Tg of greater than or equal to 40° C., for example ranging from 95 to 125° C., which is an isobornyl acrylate/isobornyl methacrylate copolymer,
      • a second block with a Tg of less than or equal to 20° C., for example ranging from −85 to −55° C., which is a 2-ethylhexyl acrylate homopolymer, and
      • an intermediate block which is an isobornyl acrylate/isobornyl methacrylate/2-ethylhexyl acrylate random copolymer.
  • According to a sixth variant, the polymer according to the invention may comprise:
      • a first block with a Tg of greater than or equal to 40° C., for example ranging from 85 to 115° C., which is an isobornyl methacrylate/isobutyl methacrylate copolymer,
      • a second block with a Tg of less than or equal to 20° C., for example ranging from −35 to −5° C., which is an isobutyl acrylate homopolymer, and
      • an intermediate block which is an isobornyl methacrylate/isobutyl methacrylate/isobutyl acrylate random copolymer.
  • According to a seventh variant, the polymer according to the invention may comprise:
      • a first block with a Tg of greater than or equal to 40° C., for example ranging from 95 to 125° C., which is an isobornyl acrylate/isobornyl methacrylate copolymer,
      • a second block with a Tg of less than or equal to 20° C., for example ranging from −35 to −5° C., which is an isobutyl acrylate homopolymer, and
      • an intermediate block which is an isobornyl acrylate/isobornyl methacrylate/isobutyl acrylate random copolymer.
  • According to an eighth variant, the polymer according to the invention may comprise:
      • a first block with a Tg of greater than or equal to 40° C., for example ranging from 60 to 90° C., which is an isobornyl acrylate/isobutyl methacrylate copolymer,
      • a second block with a Tg of less than or equal to 20° C., for example ranging from −35 to −5° C., which is an isobutyl acrylate homopolymer, and
      • an intermediate block which is an isobornyl acrylate/isobutyl methacrylate/isobutyl acrylate random copolymer.
  • The examples that follow illustrate, in a non-limiting manner, polymers corresponding to this first embodiment.
  • The amounts are expressed in grams.
  • EXAMPLE 1 Preparation of a poly(methyl methacrylate)/acrylic acid/methyl acrylate) polymer
  • 100 g of butyl acetate are introduced into a 1 litre reactor and the temperature is then raised so as to pass from room temperature (25° C.) to 90° C. in 1 hour. 180 g of methyl methacrylate, 30 g of acrylic acid, 40 g of butyl acetate, 70 g of isopropanol and 1.8 g of 2,5-bis(2-ethylhexanoylperoxy)-2,5-dimethyl-hexane (Trigonox® 141 from Akzo Nobel) are then added, at 90° C. and over 1 hour.
  • The mixture is maintained at 90° C. for 1 hour.
  • 90 g of methyl acrylate, 70 g of butyl acetate, 20 g of isopropanol and 1.2 g of 2,5-bis(2-ethylhexanoylperoxy)-2,5-dimethylhexane are then introduced into the above mixture, still at 90° C. and over 1 hour.
  • The mixture is maintained at 90° C. for 3 hours and then diluted with 105 g of butyl acetate and 45 g of isopropanol, and the mixture is then cooled.
  • A solution containing 40% polymer-active material in a butyl acetate/isopropanol mixture is obtained.
  • A polymer comprising a poly(methyl methacrylate/acrylic acid) first block with a Tg of 100° C., a polymethyl acrylate second block with a Tg of 10° C. and an intermediate block which is a methyl methacrylate/acrylic acid/polymethyl acrylate random polymer is obtained.
  • This polymer has a weight-average mass of 52 000 and a number-average mass of 18 000, i.e. a polydispersity index I of 2.89.
  • SECOND EMBODIMENT
  • According to a second embodiment, the block polymer comprises a first block having a glass transition temperature (Tg) of between 20 and 40° C., in accordance with the blocks described in c) and a second block having a glass transition temperature of less than or equal to 20° C., as described above in b) or a glass transition temperature of greater than or equal to 40° C., as described in a) above.
  • Preferably, the proportion of the first block with a Tg of between 20 and 40° C. ranges from 10% to 85% by weight of the polymer, better still from 30% to 80% and even better still from 50% to 70%.
  • When the second block is a block with a Tg of greater than or equal to 40° C., it is preferably present in a proportion ranging from 10% to 85% by weight, better still from 20% to 70% and even better still from 30% to 70% by weight of the polymer.
  • When the second block is a block with a Tg of less than or equal to 20° C., it is preferably present in a proportion ranging from 10% to 85% by weight, better still from 20% to 70% and even better still from 20% to 50% by weight of the polymer.
  • Preferably, the first block with a Tg of between 20 and 40° C. is a copolymer derived from monomers which are such that the corresponding homopolymer has a Tg of greater than or equal to 40° C., and from monomers which are such that the corresponding homopolymer has a Tg of less than or equal to 20° C.
  • Advantageously, the second block with a Tg of less than or equal to 20° C. or with a Tg of greater than or equal to 40° C. is a homopolymer.
  • Thus, according to a first variant of this second embodiment, the block polymer may comprise:
      • a first block with a Tg of between 20 and 40° C., for example with a Tg of 25 to 39° C., which is a copolymer comprising at least one methyl acrylate monomer, at least one methyl methacrylate monomer and at least one acrylic acid monomer,
      • a second block with a Tg of greater than or equal to 40° C., for example ranging from 85 to 125° C., which is a homopolymer composed of methyl methacrylate monomers, and
      • an intermediate block comprising at least one methyl acrylate, methyl methacrylate monomer, and
      • an intermediate block comprising methyl methacrylate, at least one acrylic acid monomer and at least one methyl acrylate monomer.
  • According to a second variant of this second embodiment, the block polymer may comprise:
      • a first block with a Tg of between 20 and 40° C., for example with a Tg of 21 to 39° C., which is a copolymer comprising isobornyl acrylate/isobutyl methacrylate/2-ethylhexyl acrylate,
      • a second block with a Tg of less than or equal to 20° C., for example ranging from −65 to −35° C., which is a methyl methacrylate homopolymer, and
      • an intermediate block which is an isobornyl acrylate/isobutyl methacrylate/2-ethylhexyl acrylate random copolymer.
  • According to a third variant of this second embodiment, the block polymer may comprise:
      • a first block with a Tg of between 20 and 40° C., for example with a Tg from 21 to 39° C., which is an isobornyl acrylate/methyl acrylate/acrylic acid copolymer,
      • a second block with a Tg of greater than or equal to 40° C., for example ranging from 85 to 115° C., which is an isobornyl acrylate homopolymer, and
      • an intermediate block which is an isobornyl acrylate/methyl acrylate/acrylic acid random copolymer.
  • By way of non-limiting illustration, the polymers corresponding to this second embodiment may be produced as follows.
  • EXAMPLE 2 Preparation of a poly(methyl methacrylate)/methyl acrylate/acrylic acid) polymer
  • 100 g of butyl acetate are introduced into a 1 litre reactor and the temperature is then raised so as to pass from room temperature (25° C.) to 90° C. in 1 hour. 50.4 g of methyl methacrylate, 21 g of acrylic acid, 138.6 g of methyl acrylate, 40 g of butyl acetate, 70 g of isopropanol and 1.8 g of 2,5-bis(2-ethylhexanoylperoxy)-2,5-dimethylhexane (Trigonox® 141 from Akzo Nobel) are then added, at 90° C. and over 1 hour.
  • The mixture is maintained at 90° C. for 1 hour.
  • 90 g of methyl methacrylate, 70 g of butyl acetate, 20 g of isopropanol and 1.2 g of 2,5-bis(2-ethylhexanoylperoxy)-2,5-dimethylhexane are then introduced into the above mixture, still at 90° C. and over 1 hour.
  • The mixture is maintained at 90° C. for 3 hours and then diluted with 105 g of butyl acetate and 45 g of isopropanol, and the mixture is then cooled.
  • A solution containing 40% polymer active material in a butyl acetate/isopropanol mixture is obtained.
  • The polymer obtained comprises a first poly(methyl acrylate/methyl methacrylate/acrylic acid) block with a Tg of 35° C., a second poly(methyl methacrylate) block with a Tg of 100° C. and an intermediate block that is a methyl methacrylate/acrylic acid/polymethyl acrylate random polymer.
  • Generally, the compositions of the invention contain from 0.1% to 60% by weight, preferably from 0.5% to 50% by weight and more preferably from 1% to 40% by weight of the block polymer according to the invention.
  • Solvent Medium
  • The cosmetic composition may comprise an organic solvent medium or a mixture of organic solvents.
  • The organic solvent may be chosen from:
      • ketones that are liquid at room temperature, such as methyl ethyl ketone, methyl isobutyl ketone, diisobutyl ketone, isophorone, cyclohexanone or acetone;
      • alcohols that are liquid at room temperature, such as ethanol, isopropanol, diacetone alcohol, 2-butoxy-ethanol or cyclohexanol;
      • glycols that are liquid at room temperature, such as ethylene glycol, propylene glycol, pentylene glycol or glycerol;
      • propylene glycol ethers that are liquid at room temperature such as propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate or dipropylene glycol mono-n-butyl ether; cyclic ethers such as γ-butyrolactone;
      • short-chain esters (containing from 3 to 8 carbon atoms in total) such as ethyl acetate, methyl acetate, propyl acetate, isopropyl acetate, n-butyl acetate, isopentyl acetate, methoxypropyl acetate or butyl lactate;
      • ethers that are liquid at room temperature, such as diethyl ether, dimethyl ether or dichlorodiethyl ether;
      • alkanes that are liquid at room temperature, such as decane, heptane, dodecane or cyclohexane; alkyl sulphoxides, such as dimethyl sulphoxide; aldehydes that are liquid at room temperature, such as benzaldehyde or acetaldehyde; heterocyclic compounds such as tetrahydrofuran; propylene carbonate or ethyl 3-ethoxypropionate;
      • mixtures thereof.
  • The organic solvent medium preferably has a polarity P ranging from 0.422 to 0.725.
  • The polarity is defined as a function of the solubility parameters according to the Hansen solubility space, according to the following relationship:
    P=√(δp 2 +δh 2)/δt
      • δh characterizing the specific forces of interaction (such as hydrogen bonding, acid/base bonding, donor/acceptor bonding, etc.);
      • δp characterizing the Debye interaction forces between permanent dipoles and also the Keesom interaction forces between induced dipoles and permanent dipoles; and
      • δt=√(δp2+δh2+δd2), δd characterizing the London dispersion forces derived from the formation of induced dipoles during molecular impacts.
  • The definition and calculation of the solubility parameters in the Hansen three-dimensional solubility space are described in the article by C. M. Hansen: “The three dimensional solubility parameters” J. Paint Technol. 39, 105 (1967).
  • When the solvent medium comprises a mixture of solvents, the polarity is determined from the solubility parameters of the mixture, which are themselves determined from those of the compounds taken separately, according to the following relationships: δ dmixt = i xi δ di ; δ pmixt = i xi δ pl and δ hmixt = i xi δ hi
    in which xi represents the volume fraction of the compound i in the mixture.
  • As organic solvents with a polarity ranging from 0.422 to 0.725, mention may be made in particular of methyl acetate, isopropyl acetate, methoxypropyl acetate, butyl lactate, acetone, methyl ethyl ketone, diacetone alcohol, γ-butyrolactone, tetrahydrofuran, propylene carbonate, ethyl 3-ethoxypropionate and dimethyl sulphoxide, and mixtures thereof.
  • The organic solvent medium may represent from 10% to 95% by weight, preferably from 15% to 80% by weight and better still from 20% to 60% by weight, relative to the total weight of the composition.
  • Additional Film-forming Polymer
  • The composition may comprise, besides the block polymer of the composition according to the invention, an additional polymer such as a film-forming polymer.
  • Among the film-forming polymers that may be used in the composition of the present invention, mention may be made of synthetic polymers, of free-radical type or of polycondensate type, and polymers of natural origin, and mixtures thereof.
  • The film-forming polymer may be chosen in particular from cellulose-based polymers such as cellulose acetate, cellulose acetobutyrate, cellulose acetopropionate or ethylcellulose, or alternatively polyurethanes, acrylic polymers, vinyl polymers, polyvinylbutyrals, alkyd resins, resins derived from aldehyde condensation products such as arylsulphonamide-formaldehyde resins, for instance toluenesulphonamide-formaldehyde resin, and arylsulphonamide-epoxy resins.
  • Film-forming polymers that may especially be used include the toluenesulphonamide-formaldehyde resins “Ketjentflex MS80” from the company Akzo or “Santolite MHP” or “Santolite MS 80” from the company Faconnier or “Resimpol 80” from the company Pan Americana, the alkyd resin “Beckosol ODE 230-70-E” from the company Dainippon, the acrylic resin “Acryloid B66” from the company Rohm & Haas, and the polyurethane resin “Trixene PR 4127” from the company Baxenden.
  • The additional film-forming polymer may be present in the composition according to the invention in a content ranging from 0.1% to 60% by weight, preferably ranging from 2% to 40% by weight and better still from 5% to 25% by weight, relative to the total weight of the composition.
  • Plasticizer
  • The composition may also comprise at least one plasticizer. In particular, mention may be made, alone or as a mixture, of the usual plasticizers, such as:
      • glycols and derivatives thereof such as diethylene glycol ethyl ether, diethylene glycol methyl ether, diethylene glycol butyl ether or diethylene glycol hexyl ether, ethylene glycol ethyl ether, ethylene glycol butyl ether or ethylene glycol hexyl ether;
      • glycerol esters,
      • propylene glycol derivatives and in particular propylene glycol phenyl ether, propylene glycol diacetate, dipropylene glycol butyl ether, tripropylene glycol butyl ether, propylene glycol methyl ether, dipropylene glycol ethyl ether, tripropylene glycol methyl ether, diethylene glycol methyl ether and propylene glycol butyl ether,
      • acid esters, especially carboxylic acid esters, such as citrates, phthalates, adipates, carbonates, tartrates, phosphates or sebacates,
      • oxyethylenated derivatives such as oxyethylenated oils, especially plant oils such as castor oil;
        mixtures thereof.
  • The amount of plasticizer may be chosen by a person skilled in the art on the basis of his general knowledge, so as to obtain a composition with cosmetically acceptable properties. The plasticizer is preferably present in an amount of less than 20%, preferably less than 15%, better still less than 10% and even better still less than 5% by weight, relative to the total weight of the composition. The composition according to the invention is preferably free of plasticizer.
  • Dyestuff
  • The composition according to the invention may also comprise one or more dyestuffs chosen from water-soluble dyes and pulverulent dyestuffs, for instance pigments, nacres and flakes that are 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 and preferably from 0.01% to 30% by weight, relative to the weight of the composition.
  • The term “pigments” should be understood as meaning white or coloured, mineral or organic particles of any shape, which are insoluble in the physiological medium and which are intended to colour the composition.
  • The term “nacres” should be understood as meaning iridescent particles of any shape, produced especially by certain molluscs in their shell, or alternatively synthesized.
  • The pigments may be white or coloured, and mineral and/or organic. Among the mineral pigments that may be mentioned are titanium dioxide, optionally surface-treated, zirconium oxide or cerium oxide, and also zinc oxide, iron oxide (black, yellow or red) or chromium oxide, manganese violet, ultramarine blue, chromium hydrate and ferric blue, and metal powders, for instance aluminium powder or copper powder. Among the organic pigments that may be mentioned are carbon black, pigments of D & C type, and lakes based on cochineal carmine or on barium, strontium, calcium or aluminium.
  • The nacreous pigments may be chosen from white nacreous pigments such as mica coated with titanium or with bismuth oxychloride, coloured nacreous pigments such as titanium mica coated with iron oxides, titanium mica coated especially with ferric blue or chromium oxide, titanium mica coated with an organic pigment of the abovementioned type and also nacreous pigments based on bismuth oxychloride.
  • The water-soluble dyes are, for example, beetroot juice or methylene blue.
  • The composition according to the invention may also comprise one or more fillers, especially in a content ranging from 0.01% to 50% by weight and preferably ranging from 0.01% to 30% by weight, relative to the total weight of the composition. The term “fillers” should be understood as meaning colourless or white, mineral or synthetic particles of any shape, which are 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 the texture of the composition.
  • The fillers may be mineral or organic in any form, platelet-shaped, spherical or oblong, irrespective of the crystallographic form (for example leaflet, cubic, hexagonal, orthorhombic, etc.). Mention may be made of talc, mica, silica, kaolin, polyamide (Nylon®) powders (Orgasol® from Atochem), poly-β-alanine powder and polyethylene powder, powders of polytetrafluoroethylene polymers (Teflon®), lauroyllysine, starch, boron nitride, hollow polymer microspheres such as those of polyvinylidene chloride/acrylonitrile, for instance Exapancel® (Nobel Industrie) or acrylic acid copolymers (Polytrap® from the company Dow Corning) and silicone resin microbeads (for example Tospearls® from Toshiba), elastomeric polyorganosiloxane particles, precipitated calcium carbonate, magnesium carbonate, magnesium hydrocarbonate, hydroxyapatite, hollow silica microspheres (Silica Beads® from Maprecos), glass or ceramic microcapsules, and metal soaps derived from organic carboxylic acids containing from 8 to 22 carbon atoms and preferably from 12 to 18 carbon atoms, for example zinc, magnesium or lithium stearate, zinc laurate or magnesium myristate.
  • Other Additives
  • The composition may also comprise other ingredients commonly used in cosmetic compositions. Such ingredients may be chosen from spreading agents, wetting agents, dispersants, antifoams, preserving agents, UV-screening agents, active agents, surfactants, moisturizers, fragrances, neutralizers, stabilizers and antioxidants.
  • Needless to say, a person skilled in the art will take care to select this or these optional additional compound(s), and/or the amount thereof, such that the advantageous properties of the composition according to the invention are not, or are not substantially, adversely affected by the envisaged addition.
  • Needless to say, a person skilled in the art will take care to select this or these optional additional compound(s) and/or the amount thereof, such that the advantageous properties of the composition for the use according to the invention are not, or are not substantially, adversely affected by the envisaged addition.
  • A subject of the present invention is also a cosmetic assembly comprising:
      • a container delimiting at least one compartment, the said container being closed by a closing member; and
      • a composition placed inside the said compartment, the composition being in accordance with the invention.
  • The container may be in any adequate form. It may especially be in the form of a bottle, a case or a tube.
  • The closing member may be in the form of a removable stopper.
  • The container is preferably equipped with an applicator to allow the application of the product to the nails. Such an applicator may be in the form of a fine brush consisting of at least one tuft of hairs. The tuft of hairs may be embedded at the end of a rod borne by the closing member. The hairs are preferably oriented along the axis of the rod. The hairs may be embedded by means of stapling, bonded, or obtained by moulding.
  • Alternatively, the applicator is in the form of a tape made of porous material, especially of open-cell foam or of felt.
  • Alternatively also, the applicator may be in the form of a spatula, especially made of elastomeric material.
  • 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 or by click-fastening. The term “click-fastening” 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 to the elastically unconstrained position of the said portion after the crossing of the bead or cord.
  • The container is preferably made of glass. However, materials other than glass may be used. Examples that will be mentioned include certain thermoplastic materials appropriately chosen so as to be compatible with the composition. Alternatively also, the container may be made of metal.
  • The examples that follow illustrate the invention in a non-limiting manner.
  • EXAMPLE 3 Nail Varnish
  • Polymer of Example 1 23.8 g AM
    Butyl acetate 24.99 g
    Isopropanol 10.71 g
    Hexylene glycol 2.5 g
    DC Red 7 Lake 1 g
    Hectorite modified with stearyldimethyl- 1.3 g
    benzylammonium chloride (Bentone ® 27V from
    Elementis)
  • EXAMPLE 4 Nail Varnish
  • Polymer of Example 2 23.8 g AM
    Butyl acetate 24.99 g
    Isopropanol 10.71 g
    Hexylene glycol 2.5 g
    DC Red 7 Lake 1 g
    Hectorite modified with 1.3 g
    stearyldimethylbenzylammonium chloride
    (Bentone ® 27V from Elementis)
    Ethyl acetate qs 100 g

Claims (77)

  1. 1. Nitrocellulose-free nail varnish composition, characterized in that it comprises, in a cosmetically acceptable organic solvent medium, at least one film-forming linear ethylenic block polymer, the said block polymer being such that, when it is present in sufficient amount in the composition, the mean gloss at 20° of a deposit of the said composition, once spread onto a support, is greater than or equal to 50 out of 100.
  2. 2. Composition according to claim 1, characterized in that the block polymer is non-elastomeric.
  3. 3. Composition according to claim 1 or 2, characterized in that the block polymer is free of styrene units.
  4. 4. Composition according to one of the preceding claims, characterized in that the block polymer is an ethylenic polymer derived from aliphatic ethylenic monomers comprising a carbon-carbon double bond and at least one ester group —COO— or amide —CON— group.
  5. 5. Composition according to one of the preceding claims, characterized in that the block polymer is not soluble at an active material content of at least 1% by weight in water or in a mixture of water and of linear or branched lower monoalcohols containing from 2 to 5 carbon atoms, without pH modification, at room temperature (25° C.).
  6. 6. Composition according to one of the preceding claims, characterized in that the block polymer contains first and second blocks that are linked together via an intermediate segment comprising at least one constituent monomer of the first block and at least one constituent monomer of the second block.
  7. 7. Composition according to one of the preceding claims, characterized in that the block polymer contains first and second blocks that have different glass transition temperatures (Tg).
  8. 8. Composition according to the preceding claim, characterized in that the first and second blocks are linked together via an intermediate segment with a glass transition temperature between the glass transition temperatures of the first and second blocks.
  9. 9. Composition according to any one of the preceding claims, characterized in that the block polymer contains first and second blocks that are incompatible in the said organic liquid medium.
  10. 10. Composition according to one of the preceding claims, characterized in that the block polymer has a polydispersity index I of greater than 2.
  11. 11. Composition according to claim 7, characterized in that the first block of the polymer is chosen from:
    a) a block with a Tg of greater than or equal to 40° C.,
    b) a block with a Tg of less than or equal to 20° C.,
    c) a block with a Tg of between 20 and 40° C., and
    the second block is chosen from a category a), b) or c) that is different from the first block.
  12. 12. Composition according to claim 11, characterized in that the block with a Tg of greater than or equal to 40° C. is totally or partially derived from one or more monomers which are such that the homopolymer prepared from these monomers has a glass transition temperature of greater than or equal to 40° C.
  13. 13. Composition according to the preceding claim, characterized in that the monomers whose corresponding homopolymer has a glass transition temperature of greater than or equal to 40° C. are chosen from the following monomers:
    methacrylates of formula CH2═C(CH3)—COOR1
    in which R1 represents a linear or branched unsubstituted alkyl group containing from 1 to 4 carbon atoms, such as a methyl, ethyl, propyl or isobutyl group or R1 represents a C4 to C12 cycloalkyl group,
    acrylates of formula CH2═CH—COOR2
    in which R2 represents a C4 to C12 cycloalkyl group such as isobornyl acrylate or a tert-butyl group,
    (meth)acrylamides of formula:
    Figure US20060134032A1-20060622-C00002
    in which R7 and R8, which may be identical or different, each represent a hydrogen atom or a linear or branched alkyl group with 1 to 12 carbon atoms such as an n-butyl, t-butyl, isopropyl, isohexyl, isooctyl or isononyl group; or R7 represents H and R8 represents a 1,1-dimethyl-3-oxobutyl group, and R′ denotes H or methyl,
    and mixtures thereof.
  14. 14. Composition according to claim 12 or 13, characterized in that the monomers whose corresponding homopolymer has a glass transition temperature of greater than or equal to 40° C. are chosen from methyl methacrylate, isobutyl (meth)acrylate and isobornyl (meth)acrylate, and mixtures thereof.
  15. 15. Composition according to claim 11, characterized in that the block with a Tg of less than or equal to 20° C. is totally or partially derived from one or more monomers which are such that the homopolymer prepared from these monomers has a glass transition temperature of less than or equal to 20° C.
  16. 16. Composition according to claim 15, characterized in that the monomers whose corresponding homopolymer has a glass transition temperature of less than or equal to 20° C. are chosen from the following monomers:
    acrylates of formula CH2═CHCOOR3,
    R3 representing a linear or branched C1 to C12 unsubstituted alkyl group, with the exception of the tert-butyl group, in which one or more hetero atoms chosen from O, N and S is (are) optionally intercalated;
    methacrylates of formula CH2═C(CH3)—COOR4,
    R4 representing a linear or branched C6 to C12 unsubstituted alkyl group, in which one or more hetero atoms chosen from O, N and S is (are) optionally intercalated;
    vinyl esters of formula R5—CO—O—CH═CH2
    in which R5 represents a linear or branched C4 to C12 alkyl group;
    C4 to C12 alkyl vinyl ethers,
    N-(C4 to C12)alkyl acrylamides, such as N-octylacrylamide;
    and mixtures thereof.
  17. 17. Composition according to claim 15 or 16, characterized in that the monomers whose corresponding homopolymer has a glass transition temperature of less than or equal to 20° C. are chosen from alkyl acrylates whose alkyl chain contains from 1 to 10 carbon atoms, with the exception of the tert-butyl group.
  18. 18. Composition according to claim 11, characterized in that the block with a Tg of between 20 and 40° C. is totally or partially derived from one or more monomers which are such that the homopolymer prepared from these monomers has a glass transition temperature of between 20 and 40° C.
  19. 19. Composition according to claim 11, characterized in that the block with a Tg of between 20 and 40° C. is totally or partially derived from monomers which are such that the corresponding homopolymer has a Tg of greater than or equal to 40° C. and from monomers which are such that the corresponding homopolymer has a Tg of less than or equal to 20° C.
  20. 20. Composition according to claim 18 or 19, characterized in that the block with a Tg of between 20 and 40° C. is totally or partially derived from monomers chosen from methyl methacrylate, isobornyl acrylate, isobornyl methacrylate, butyl acrylate and 2-ethylhexyl acrylate, and mixtures thereof.
  21. 21. Composition according to one of claims 11 to 20, characterized in that it comprises a block polymer comprising at least a first block and at least a second block, the first block having a glass transition temperature (Tg) of greater than or equal to 40° C., and the second block having a glass transition temperature of less than or equal to 20° C.
  22. 22. Composition according to the preceding claim, characterized in that the first block is totally or partially derived from one or more monomers which are such that the homopolymer prepared from these monomers has a glass transition temperature of greater than or equal to 40° C.
  23. 23. Composition according to claim 22, characterized in that the first block is a copolymer derived from monomers which are such that the homopolymer prepared from these monomers has a glass transition temperature of greater than or equal to 40° C.
  24. 24. Composition according to claim 22 or 23, characterized in that the monomers whose corresponding homopolymer has a glass transition temperature of greater than or equal to 40° C. are chosen from the following monomers:
    methacrylates of formula CH2═C(CH3)—COOR1
    in which R1 represents a linear or branched unsubstituted alkyl group containing from 1 to 4 carbon atoms, such as a methyl, ethyl, propyl or isobutyl group or R1 represents a C4 to C12 cycloalkyl group,
    acrylates of formula CH2═CH—COOR2
    in which R2 represents a C4 to C12 cycloalkyl group such as isobornyl acrylate or a tert-butyl group,
    (meth)acrylamides of formula:
    Figure US20060134032A1-20060622-C00003
    in which R7 and R8, which may be identical or different, each represent a hydrogen atom or a linear or branched alkyl group with 1 to 12 carbon atoms such as an n-butyl, t-butyl, isopropyl, isohexyl, isooctyl or isononyl group; or R7 represents H and R8 represents a 1,1-dimethyl-3-oxobutyl group, and R′ denotes H or methyl,
    and mixtures thereof.
  25. 25. Composition according to one of claims 22 to 24, characterized in that the monomers whose corresponding homopolymer has a glass transition temperature of greater than or equal to 40° C. are chosen from methyl methacrylate, isobutyl methacrylate and isobornyl (meth)acrylate, and mixtures thereof.
  26. 26. Composition according to one of claims 22 to 25, characterized in that the proportion of the first block ranges from 20% to 90%, better still from 30% to 80% and even better still from 50% to 70%, by weight of the polymer.
  27. 27. Composition according to one of claims 21 to 26, characterized in that the second block is totally or partially derived from one or more monomers which are such that the homopolymer prepared from these monomers has a glass transition temperature of less than or equal to 20° C.
  28. 28. Composition according to one of claims 21 to 27, characterized in that the second block is a homopolymer derived from monomers which are such that the homopolymer prepared from these monomers has a glass transition temperature of less than or equal to 20° C.
  29. 29. Composition according to one of claims 27 or 28, characterized in that the monomers whose corresponding homopolymer has a glass transition temperature of less than or equal to 20° C. are chosen from the following monomers:
    acrylates of formula CH2═CHCOOR3,
    R3 representing a linear or branched C1 to C12 unsubstituted alkyl group, with the exception of the tert-butyl group, in which one or more hetero atoms chosen from O, N and S is (are) optionally intercalated;
    methacrylates of formula CH2═C(CH3)—COOR4,
    R4 representing a linear or branched C6 to C12 unsubstituted alkyl group, in which one or more hetero atoms chosen from O, N and S is (are) optionally intercalated;
    vinyl esters of formula R5—CO—O—CH═CH2
    in which R5 represents a linear or branched C4 to C12 alkyl group;
    C4 to C12 alkyl vinyl ethers,
    N-(C4 to C12)alkyl acrylamides, such as N-octylacrylamide;
    and mixtures thereof.
  30. 30. Composition according to one of claims 27 to 29, characterized in that the monomers whose corresponding homopolymer has a glass transition temperature of less than or equal to 20° C. are chosen from alkyl acrylates whose alkyl chain contains from 1 to 10 carbon atoms, with the exception of the tert-butyl group.
  31. 31. Composition according to one of claims 21 to 30, characterized in that the proportion of the second block with a Tg of less than or equal to 20° C. ranges from 5% to 75%, better still from 15% to 50% and even better still from 25% to 45%, by weight of the polymer.
  32. 32. Composition according to one of claims 11 to 20, characterized in that it comprises a block polymer comprising at least a first block and at least a second block, the first block having a glass transition temperature (Tg) of between 20 and 40° C. and the second block having a glass transition temperature of less than or equal to 20° C. or a glass transition temperature of greater than or equal to 40° C.
  33. 33. Composition according to the preceding claim, characterized in that the first block with a Tg of between 20 and 40° C. is totally or partially derived from one or more monomers which are such that the homopolymer prepared from these monomers has a glass transition temperature of between 20 and 40° C.
  34. 34. Composition according to claim 32 or 33, characterized in that the first block with a Tg of between 20 and 40° C. is a copolymer derived from monomers which are such that the corresponding homopolymer has a Tg of greater than or equal to 40° C., and from monomers which are such that the corresponding homopolymer has a Tg of less than or equal to 20° C.
  35. 35. Composition according to one of claims 32 to 34, characterized in that the first block with a Tg of between 20 and 40° C. is derived from monomers chosen from methyl methacrylate, isobornyl acrylate, isobornyl methacrylate, butyl acrylate and 2-ethylhexyl acrylate, and mixtures thereof.
  36. 36. Composition according to one of claims 32 to 35, characterized in that the proportion of the first block with a Tg of between 20 and 40° C. ranges from 10% to 85%, better still from 30% to 80% and even better still from 50% to 70% by weight of the polymer.
  37. 37. Composition according to any one of claims 32 to 35, characterized in that the second block has a Tg of greater than or equal to 40° C. and is totally or partially derived from one or more monomers which are such that the homopolymer prepared from these monomers has a glass transition temperature of greater than or equal to 40° C.
  38. 38. Composition according to any one of claims 32 to 37, characterized in that the second block has a Tg of greater than or equal to 40° C. and is a homopolymer derived from monomers which are such that the homopolymer prepared from these monomers has a glass transition temperature of greater than or equal to 40° C.
  39. 39. Composition according to either of claims 37 and 38, characterized in that the monomers whose corresponding polymer has a glass transition temperature of greater than or equal to 40° C. are chosen from the following monomers:
    methacrylates of formula CH2═C(CH3)—COOR1
    in which R1 represents a linear or branched unsubstituted alkyl group containing from 1 to 4 carbon atoms, such as a methyl, ethyl, propyl or isobutyl group or R1 represents a C4 to C12 cycloalkyl group,
    acrylates of formula CH2═CH—COOR2
    in which R2 represents a C4 to C12 cycloalkyl group such as isobornyl acrylate or a tert-butyl group,
    (meth)acrylamides of formula:
    Figure US20060134032A1-20060622-C00004
    in which R7 and R8, which may be identical or different, each represent a hydrogen atom or a linear or branched alkyl group with 1 to 12 carbon atoms such as an n-butyl, t-butyl, isopropyl, isohexyl, isooctyl or isononyl group; or R7 represents H and R8 represents a 1,1-dimethyl-3-oxobutyl group, and R′ denotes H or methyl,
    and mixtures thereof.
  40. 40. Composition according to one of claims 36 to 39, characterized in that the monomers whose corresponding homopolymer has a glass transition temperature of greater than or equal to 40° C. are chosen from methyl methacrylate, isobutyl methacrylate and isobornyl (meth)acrylate, and mixtures thereof.
  41. 41. Composition according to one of claims 37 to 40, characterized in that the proportion of the second block with a Tg of greater than or equal to 40° C. ranges from 10% to 85%, preferably from 20% to 70% and better still from 30% to 70%, by weight of the polymer.
  42. 42. Composition according to one of claims 32 to 41, characterized in that the second block has a Tg of less than or equal to 20° C. and is totally or partially derived from one or more monomers which are such that the homopolymer prepared from these monomers has a glass transition temperature of less than or equal to 20° C.
  43. 43. Composition according to one of claims 32 to 41, characterized in that the second block has a Tg of less than or equal to 20° C. and is a homopolymer derived from monomers which are such that the homopolymer prepared from these monomers has a glass transition temperature of less than or equal to 20° C.
  44. 44. Composition according to claim 42 or 43, characterized in that the monomers whose corresponding homopolymer has a glass transition temperature of less than or equal to 20° C. are chosen from the following monomers:
    acrylates of formula CH2═CHCOOR3,
    R3 representing a linear or branched C1 to C12 unsubstituted alkyl group, with the exception of the tert-butyl group, in which one or more hetero atoms chosen from O, N and S is (are) optionally intercalated;
    methacrylates of formula CH2═C(CH3)—COOR4,
    R4 representing a linear or branched C6 to C12 unsubstituted alkyl group, in which one or more hetero atoms chosen from O, N and S is (are) optionally intercalated;
    vinyl esters of formula R5—CO—O—CH═CH2
    in which R5 represents a linear or branched C4 to C12 alkyl group;
    C4 to C12 alkyl vinyl ethers,
    N-(C4 to C12)alkyl acrylamides, such as N-octylacrylamide;
    and mixtures thereof.
  45. 45. Composition according to one of claims 42 to 44, characterized in that the monomers whose homopolymers have glass transition temperatures of less than or equal to 20° C. are chosen from alkyl acrylates whose alkyl chain contains from 1 to 10 carbon atoms, with the exception of the tert-butyl group.
  46. 46. Composition according to one of claims 42 to 45, characterized in that the proportion of the block with a glass transition temperature of greater than or equal to 40° C. ranges from 20% to 90%, better still from 30% to 80% and even better still from 50% to 70%, by weight of the polymer.
  47. 47. Composition according to one of claims 5 to 8 or any one of their preceding dependant claims, characterized in that the first block and/or the second block comprises at least one additional monomer.
  48. 48. Composition according to the preceding claim, characterized in that the additional monomer is chosen from hydrophilic monomers and ethylenically unsaturated monomers comprising one or more silicon atoms, and mixtures thereof.
  49. 49. Composition according to claim 47 or 48, characterized in that the additional monomer is chosen from:
    a) hydrophilic monomers such as:
    ethylenically unsaturated monomers comprising at least one carboxylic or sulfonic acid function, for instance:
    acrylic acid, methacrylic acid, crotonic acid, maleic anhydride, itaconic acid, fumaric acid, maleic acid, acrylamidopropanesulfonic acid, vinylbenzoic acid, vinylphosphoric acid, and salts thereof,
    ethylenically unsaturated monomers comprising at least one tertiary amine function, for instance 2-vinylpyridine, 4-vinylpyridine, dimethylaminoethyl methacrylate, diethylaminoethyl methacrylate and dimethylaminopropylmethacrylamide, and salts thereof,
    methacrylates of formula CH2═C(CH3)—COOR6 in which R6 represents a linear or branched alkyl group containing from 1 to 4 carbon atoms, such as a methyl, ethyl, propyl or isobutyl group, the said alkyl group being substituted with one or more substituents chosen from hydroxyl groups (for instance 2-hydroxypropyl methacrylate and 2-hydroxyethyl methacrylate) and halogen atoms (Cl, Br, I or F), such as trifluoroethyl methacrylate,
    methacrylates of formula CH2═C(CH3)—COOR9,
    R9 representing a linear or branched C6 to C12 alkyl group in which one or more hetero atoms chosen from O, N and S is (are) optionally intercalated, the said alkyl group being substituted with one or more substituents chosen from hydroxyl groups and halogen atoms (Cl, Br, I or F);
    acrylates of formula CH2═CHCOOR10,
    R10 representing a linear or branched C1 to C12 alkyl group substituted with one or more substituents chosen from hydroxyl groups and halogen atoms (Cl, Br, I or F), such as 2-hydroxypropyl acrylate and 2-hydroxyethyl acrylate, or R10 represents a (C1 to C12) alkyl-O-POE (polyoxyethylene) with repetition of the oxyethylene unit 5 to 30 times, for example methoxy-POE, or R10 represents a polyoxyethylenated group comprising from 5 to 30 ethylene oxide units, and
    b) ethylenically unsaturated monomers comprising one or more silicon atoms, such as methacryloxypropyltrimethoxysilane and methacryloxypropyltris(trimethylsiloxy)silane,
    and mixtures thereof.
  50. 50. Composition according to either of claims 47 and 48, characterized in that each of the first and second blocks comprises at least one additional monomer chosen from acrylic acid, (meth)acrylic acid and trifluoroethyl methacrylate, and mixtures thereof.
  51. 51. Composition according to either of claims 47 and 48, characterized in that each of the first and second blocks comprises at least one monomer chosen from (meth)acrylic acid esters and optionally at least one additional monomer such as (meth)acrylic acid, and mixtures thereof.
  52. 52. Composition according to either of claims 47 and 48, characterized in that each of the first and second blocks is totally derived from at least one monomer chosen from (meth)acrylic acid esters and optionally from at least one additional monomer such as (meth)acrylic acid, and mixtures thereof.
  53. 53. Composition according to one of claims 47 to 52, characterized in that the additional monomer(s) represent(s) from 1% to 30% by weight relative to the total weight of the first and/or second blocks.
  54. 54. Composition according to claim 7 or any one of its preceding dependant claims, characterized in that the difference between the glass transition temperatures (Tg) of the first and second blocks is greater than 10° C., better still greater than 20° C., preferably greater than 30° C. and better still greater than 40° C.
  55. 55. Composition according to claim 10, characterized in that the block polymer has a polydispersity index of greater than or equal to 2.5 and preferably greater than or equal to 2.8.
  56. 56. Composition according to claim 55, characterized in that has a polydispersity index of between 2.8 and 6.
  57. 57. Composition according to one of the preceding claims, characterized in that the block polymer has a weight-average mass (Mw) which is less than or equal to 300 000.
  58. 58. Composition according to claim 57, characterized in that the weight-average mass (Mw) ranges from 35 000 to 200 000 and better still from 45 000 to 150 000.
  59. 59. Composition according to claim 58, characterized in that the wight-average mass (Mn) is less than or equal to 70 000.
  60. 60. Composition according to one of claims 57 to 59, whose weight-average mass (Mn) ranges from 10 000 to 60 000 and better still from 12 000 to 50 000.
  61. 61. Composition according to any one of the preceding claims, characterized in that it comprises from 0.1% to 60% by weight of polymer active material, preferably from 5% to 50% by weight and more preferably from 10% to 40% by weight.
  62. 62. Composition according to one of the preceding claims, characterized in that the organic solvent medium comprises an organic solvent chosen from:
    ketones that are liquid at room temperature, such as methyl ethyl ketone, methyl isobutyl ketone, diisobutyl ketone, isophorone, cyclohexanone or acetone;
    alcohols that are liquid at room temperature, such as ethanol, isopropanol, diacetone alcohol, 2-butoxy-ethanol or cyclohexanol;
    glycols that are liquid at room temperature, such as ethylene glycol, propylene glycol, pentylene glycol or glycerol;
    propylene glycol ethers that are liquid at room temperature such as propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate or dipropylene glycol mono-n-butyl ether; cyclic ethers such as γ-butyrolactone;
    short-chain esters (containing from 3 to 8 carbon atoms in total) such as ethyl acetate, methyl acetate, propyl acetate, isopropyl acetate, n-butyl acetate, isopentyl acetate, methoxypropyl acetate or butyl lactate;
    ethers that are liquid at room temperature, such as diethyl ether, dimethyl ether or dichlorodiethyl ether;
    alkanes that are liquid at room temperature, such as decane, heptane, dodecane or cyclohexane;
    alkyl sulphoxides, such as dimethyl sulphoxide;
    aldehydes that are liquid at room temperature, such as benzaldehyde or acetaldehyde;
    heterocyclic compounds such as tetrahydrofuran;
    propylene carbonate or ethyl 3-ethoxypropionate;
    mixtures thereof.
  63. 63. Composition according to claim 62, characterized in that the organic solvent medium has a polarity P ranging from 0.422 to 0.725.
  64. 64. Composition according to claim 62 or 63, characterized in that the organic solvent medium represents from 10% to 95% by weight, preferably from 15% to 80% by weight and better still from 20% to 60% by weight, relative to the total weight of the composition.
  65. 65. Composition according to any one of the preceding claims, characterized in that it comprises a dyestuff.
  66. 66. Composition according to the preceding claim, characterized in that the dyestuff is present in a content ranging from 0.01% to 50% by weight and preferably from 0.01% to 30% by weight, relative to the total weight of the composition.
  67. 67. Composition according to the preceding claim, characterized in that it contains a plasticizer, which is present in an amount of less than 20%, preferably less than 15%, better still less than 10% and even better still less than 5% by weight, relative to the total weight of the composition.
  68. 68. Composition according to the preceding claim, characterized in that the mean gloss of the composition measured at 20° is greater than or equal to 50 out of 100, better still greater than or equal to 55, even better still greater than or equal to 60, even better still greater than or equal to 65, even better still greater than or equal to 70 or even better still greater than or equal to 75 out of 100, or even greater than or equal to 80 out of 100.
  69. 69. Composition according to the preceding claim, characterized in that the mean gloss of the composition, once spread onto a support, measured at 60° is greater than or equal to 50, better still greater than or equal to 60, better still greater than or equal to 65, better still greater than or equal to 70, better still greater than or equal to 75, better still greater than or equal to 80, better still greater than or equal to 85 or better still greater than or equal to 90 out of 100.
  70. 70. Cosmetic assembly comprising:
    a) a container delimiting at least one compartment, the said container being closed by a closing member; and
    b) a composition placed inside the said compartment, the composition being in accordance with any one of the preceding claims.
  71. 71. Cosmetic assembly according to claim 70, characterized in that the container is at least partly made of glass.
  72. 72. Cosmetic assembly according to claim 70, characterized in that the container is at least partly made of at least one material other than glass.
  73. 73. Assembly according to any one of claims 70 to 72, characterized in that, in the closed position of the container, the closing member is screwed onto the container.
  74. 74. Assembly according to any one of claims 70 to 72, characterized in that, in the closed position of the container, the closing member is coupled to the container other than by screwing, especially by click-fastening.
  75. 75. Assembly according to any one of claims 70 to 74, characterized in that it comprises an applicator in the form of a fine brush comprising at least one tuft of hairs.
  76. 76. Assembly according to any one claims 70 to 74, characterized in that it comprises an applicator other than a fine brush.
  77. 77. Non-therapeutic cosmetic makeup or care process for the nails, comprising the application to the nails of at least one coat of a nail varnish composition according to one of claims 1 to 69.
US10528699 2002-09-26 2003-09-26 Nail varnish composition comprising a sequenced polymer Abandoned US20060134032A1 (en)

Priority Applications (7)

Application Number Priority Date Filing Date Title
FR0211949 2002-09-26
FR0211949 2002-09-26
FR0216437 2002-12-20
FR0216437 2002-12-20
FR0306121 2003-05-21
FR0306121 2003-05-21
PCT/FR2003/002846 WO2004028494A3 (en) 2002-09-26 2003-09-26 Nail varnish composition comprising a sequenced polymer

Publications (1)

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US20060134032A1 true true US20060134032A1 (en) 2006-06-22

Family

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Family Applications (10)

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US10670388 Abandoned US20040120906A1 (en) 2002-09-26 2003-09-26 Nail varnish composition comprising a block polymer
US10528699 Abandoned US20060134032A1 (en) 2002-09-26 2003-09-26 Nail varnish composition comprising a sequenced polymer
US10528835 Active 2028-09-08 US8992903B2 (en) 2002-09-26 2003-09-26 Composition comprising at least one block polymer and at least one gelling agent
US10529218 Abandoned US20060115444A1 (en) 2002-09-26 2003-09-26 Glossy liquid composition comprising a sequenced polymer
US10529265 Active 2029-03-28 US9017704B2 (en) 2002-09-26 2003-09-26 Composition comprising a block polymer and a film-forming agent
US10528698 Abandoned US20060127334A1 (en) 2002-09-26 2003-09-26 Lipstick comprising a sequenced polymer
US10529267 Abandoned US20060099164A1 (en) 2002-09-26 2003-09-26 Composition for coating keratin fibres, comprising a high dry extract that contains a sequenched polymer
US10529318 Expired - Fee Related US7875265B2 (en) 2002-09-26 2003-09-26 Cosmetic composition comprising a sequenced polymer and a plasticizer
US10529264 Abandoned US20060147403A1 (en) 2002-09-26 2003-09-26 Non-transfer cosmetic composition comprising a sequenced polymer
US10529266 Abandoned US20060134051A1 (en) 2002-09-26 2003-09-26 Glossy non-transfer composition comprising a sequenced polymer

Family Applications Before (1)

Application Number Title Priority Date Filing Date
US10670388 Abandoned US20040120906A1 (en) 2002-09-26 2003-09-26 Nail varnish composition comprising a block polymer

Family Applications After (8)

Application Number Title Priority Date Filing Date
US10528835 Active 2028-09-08 US8992903B2 (en) 2002-09-26 2003-09-26 Composition comprising at least one block polymer and at least one gelling agent
US10529218 Abandoned US20060115444A1 (en) 2002-09-26 2003-09-26 Glossy liquid composition comprising a sequenced polymer
US10529265 Active 2029-03-28 US9017704B2 (en) 2002-09-26 2003-09-26 Composition comprising a block polymer and a film-forming agent
US10528698 Abandoned US20060127334A1 (en) 2002-09-26 2003-09-26 Lipstick comprising a sequenced polymer
US10529267 Abandoned US20060099164A1 (en) 2002-09-26 2003-09-26 Composition for coating keratin fibres, comprising a high dry extract that contains a sequenched polymer
US10529318 Expired - Fee Related US7875265B2 (en) 2002-09-26 2003-09-26 Cosmetic composition comprising a sequenced polymer and a plasticizer
US10529264 Abandoned US20060147403A1 (en) 2002-09-26 2003-09-26 Non-transfer cosmetic composition comprising a sequenced polymer
US10529266 Abandoned US20060134051A1 (en) 2002-09-26 2003-09-26 Glossy non-transfer composition comprising a sequenced polymer

Country Status (5)

Country Link
US (10) US20040120906A1 (en)
EP (10) EP1545442B1 (en)
JP (8) JP3981131B2 (en)
DE (7) DE60334709D1 (en)
WO (10) WO2004028492A3 (en)

Cited By (14)

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Publication number Priority date Publication date Assignee Title
US20040120906A1 (en) * 2002-09-26 2004-06-24 Beatrice Toumi Nail varnish composition comprising a block polymer
US20050220747A1 (en) * 2004-03-25 2005-10-06 Bertrand Lion Styling composition comprising, in a predominantly aqueous medium, a pseudo-block polymer, processes employing same and uses thereof
US20050220731A1 (en) * 2004-03-23 2005-10-06 Philippe Ilekti Nail varnish composition comprising at least one polymer and at least one plasticizer
US20070196306A1 (en) * 2005-07-22 2007-08-23 Nathalie Jager Lezer Process for coating eyelashes
US20080014234A1 (en) * 2002-09-26 2008-01-17 L'oreal Novel Block Polymers and Cosmetic Compositions and Processes Comprising Them
US20080145325A1 (en) * 2006-09-13 2008-06-19 Lizabeth-Anne Coffey-Dawe Nail varnish comprising at least one resin
US20100215605A1 (en) * 2008-11-24 2010-08-26 L'oreal Solid cosmetic composition for application to keratin fibres
US20110020263A1 (en) * 2009-06-01 2011-01-27 L'oreal Composition containing a block polymer and a nonvolatile ester oil
US8119110B2 (en) 2003-09-26 2012-02-21 L'oreal S.A. Cosmetic composition comprising a block polymer and a non-volatile silicone oil
US20120118314A1 (en) * 2009-07-21 2012-05-17 Danny Lee Haile Compositions for removable gel applications for nails and methods of their use
US20130213426A1 (en) * 2010-11-02 2013-08-22 L'oreal Two-step nail polish product
US8710152B2 (en) 2006-07-27 2014-04-29 L'oreal Block polymers and their process of preparation
US9125468B2 (en) 2010-03-29 2015-09-08 L'oreal Device for the application of fibers to human keratinous fibers
US20170360683A1 (en) * 2016-06-15 2017-12-21 Mycone Dental Supply Co., Inc. One Part Acrylic Nail Formulation

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* Cited by examiner, † Cited by third party
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JP2006525960A (en) 2003-02-19 2006-11-16 ライナット ニューロサイエンス コーポレイション Methods for treating pain by administration of nerve growth factor agonists and NSAID, and compositions containing them
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DE10358091A1 (en) * 2003-12-10 2005-07-14 Eckart Gmbh & Co. Kg Cosmetic composition for creating a cosmetic coating having a metallic and multicolored iridescent appearance and artificial fingernail
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US20050281769A1 (en) * 2004-06-11 2005-12-22 Toumi Beatrice Cosmetic composition comprising a polymer
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US20060193803A1 (en) * 2005-02-04 2006-08-31 Celine Farcet Polymer particle dispersions, cosmetic compositions comprising at least one polymer particle dispersion, and cosmetic process using same
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FR2887770A1 (en) * 2005-07-04 2007-01-05 Oreal Make-up or care product comprises a first composition comprising a block copolymer with at least one block of variable conformation and a second composition comprising an oil with defined properties
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US20070081954A1 (en) * 2005-10-06 2007-04-12 Nathalie Mougin Dispersion of polymer particles, composition comprising it and cosmetic treatment method
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US20070134181A1 (en) * 2005-12-08 2007-06-14 L'oreal Cosmetic composition comprising an ester of dimerdilinoleic acid and of polyol(s) and a silicone surfactant
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CA2635683A1 (en) * 2005-12-30 2007-07-12 Avon Products, Inc. Method for imparting curl to eyelashes
US20070207096A1 (en) * 2006-02-13 2007-09-06 Virginie Puisset Nail varnish having a gelled texture
DE102006012354A1 (en) * 2006-03-17 2007-09-20 Bayer Materialscience Ag Aqueous dispersions based on nitrocellulose polyurethane particles
JP2007308544A (en) * 2006-05-17 2007-11-29 Hitachi Ltd Nano composite material having low dielectric constant and low refractive index
FR2902006B1 (en) * 2006-06-13 2009-06-05 Oreal Cosmetic composition for the lips associating a phosphate surfactant and a silicone polymer
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EP1913975B1 (en) * 2006-10-20 2011-06-08 Faber-Castell AG Cosmetic preparation for dyeing eyelashes and eyebrows
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FR2910280B1 (en) 2006-12-22 2009-01-23 Oreal Nail polish comprising a polycondensate and a polyoxyalkylene copolymer
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US20080260665A1 (en) * 2007-01-08 2008-10-23 Laurence Guerchet Nail varnish comprising at least one polycondensate and at least one polyoxyalkylene copolymer
FR2915892B1 (en) 2007-05-10 2009-07-03 Oreal Composition in foam form comprising a polymeric structurant
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US20090035335A1 (en) * 2007-07-30 2009-02-05 Marotta Paul H Cosmetic Composition Containing a Polymer Blend
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KR101773683B1 (en) * 2014-12-15 2017-08-31 주식회사 엘지생활건강 Skin external preparation composition
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KR101773682B1 (en) * 2014-12-15 2017-08-31 주식회사 엘지생활건강 Skin external preparation composition
KR101773681B1 (en) * 2014-12-15 2017-08-31 주식회사 엘지생활건강 Skin external preparation composition
KR101773680B1 (en) * 2014-12-15 2017-08-31 주식회사 엘지생활건강 Skin external preparation composition
FR3030260B1 (en) * 2014-12-18 2017-01-13 Oreal A composition comprising polymer particles stabilized and a nonionic surfactant
FR3030261B1 (en) * 2014-12-18 2017-01-13 Oreal A composition comprising polymer particles stabilized and a hydrophobic film-forming polymer
FR3052972B1 (en) * 2016-06-23 2018-08-03 Oreal Method for elongation and / or densification of the fibers

Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4425326A (en) * 1980-04-01 1984-01-10 Societe Anonyme Dite : L'oreal Anhydrous nail varnishes
US6410005B1 (en) * 2000-06-15 2002-06-25 Pmd Holdings Corp. Branched/block copolymers for treatment of keratinous substrates
US20030059392A1 (en) * 2001-07-18 2003-03-27 L'oreal Composition for topical use containing a diblock polymer
US20040009136A1 (en) * 2002-05-31 2004-01-15 L'oreal Aqueous hair treatment compositions, thickened with an amphiphilic linear block copolymer
US6692733B1 (en) * 1999-04-06 2004-02-17 L'oreal Composition comprising polymers having a star structure, the polymers, and their use
US20040039101A1 (en) * 2002-05-31 2004-02-26 Claude Dubief Washing compositions comprising at least one amphiphilic block copolymer and at least one cationic or amphoteric polymer
US20040077788A1 (en) * 2002-07-19 2004-04-22 Cid Centro De Investigacion Y Desarrollo Tecnologico, S.A. De. C.V. Block copolymers containing functional groups
US20040120920A1 (en) * 2002-09-26 2004-06-24 Bertrand Lion Novel block polymers and cosmetic compositions and processes comprising them
US20040120906A1 (en) * 2002-09-26 2004-06-24 Beatrice Toumi Nail varnish composition comprising a block polymer
US20050106197A1 (en) * 2003-09-26 2005-05-19 Xavier Blin Cosmetic composition comprising a block polymer and a non-volatile silicone oil

Family Cites Families (272)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US811910A (en) * 1903-03-12 1906-02-06 Albert H Emery Cartridge.
BE380814A (en) 1930-06-26
US2528378A (en) 1947-09-20 1950-10-31 John J Mccabe Jr Metal salts of substituted quaternary hydroxy cycloimidinic acid metal alcoholates and process for preparation of same
US2723248A (en) 1954-10-01 1955-11-08 Gen Aniline & Film Corp Film-forming compositions
US2781354A (en) 1956-03-26 1957-02-12 John J Mccabe Jr Imidazoline derivatives and process
FR1222944A (en) 1958-04-15 1960-06-14 Hoechst Ag graft polymers and their method of preparation
FR1400366A (en) 1963-05-15 1965-05-28 Oreal New compounds that can be used especially for the treatment of hair
US4129711A (en) 1965-03-03 1978-12-12 L'oreal Polymers comprising vinyl esters-crotonic acid
US3925542A (en) 1965-03-03 1975-12-09 Oreal Hair lacquer and wave setting compositions containing vinyl acetate-crotonic acid-containing polymers
FR1517743A (en) * 1966-08-03 1968-03-22 Oreal New copolymers and cosmetic compositions containing these copolymers
NL136457C (en) 1967-03-23
LU54202A1 (en) 1967-07-28 1969-03-24
US3910862A (en) 1970-01-30 1975-10-07 Gaf Corp Copolymers of vinyl pyrrolidone containing quarternary ammonium groups
DE2103898C2 (en) 1970-01-30 1983-07-28 Gaf Corp
FR2079785A5 (en) 1970-02-12 1971-11-12 Rhodiaceta Lustrous polyamide-imide based fibres by new process
FI55686C (en) * 1970-02-12 1979-09-10 Rhodiaceta Foerfarande Foer framstaellning of Blanka vaermebestaendiga polyamidimidfibrer
US4032628A (en) 1970-04-07 1977-06-28 Societe Anonyme Dite: L'oreal Cosmetic emulsion compositions including black polymer emulsifiers
LU60676A1 (en) 1970-04-07 1972-02-10
US3836537A (en) 1970-10-07 1974-09-17 Minnesota Mining & Mfg Zwitterionic polymer hairsetting compositions and method of using same
FR2141556B1 (en) * 1971-06-14 1974-03-22 Rhone Poulenc Textile
FR2140977A5 (en) 1971-10-26 1973-01-19 Oreal Sequenced polymers - from lipophilic and hydrophilic monomers for cosmetic use
CA981183A (en) 1972-04-14 1976-01-06 Albert L. Micchelli Hair fixing compositions
LU65552A1 (en) 1972-06-20 1973-12-27
USRE29871E (en) 1973-06-08 1978-12-26 L'oreal Fatty compositions for use in cosmetic makeup compositions and said cosmetic makeup compositions
LU67772A1 (en) 1973-06-08 1975-03-06
LU69760A1 (en) 1974-04-01 1976-03-17
US4070533A (en) * 1974-04-01 1978-01-24 L'oreal Terpolymer of (a) crotonic acid (b) vinyl acetate and (c) allyl or methallyl esters
LU69759A1 (en) 1974-04-01 1976-03-17
US4076912A (en) * 1974-04-01 1978-02-28 L'oreal Tetrapolymers comprising (a) unsaturated acids (b) vinyl esters (c) branched allyl or methallyl esters and (d) vinyl ether or vinyl fatty ester or linear allyl or methallyl esters
US3915921A (en) 1974-07-02 1975-10-28 Goodrich Co B F Unsaturated carboxylic acid-long chain alkyl ester copolymers and tri-polymers water thickening agents and emulsifiers
LU71577A1 (en) * 1974-12-30 1976-11-11
JPS6213364B2 (en) 1976-04-06 1987-03-26 Oreal
FR2360615B1 (en) 1976-04-06 1981-02-13 Oreal
US4031307A (en) * 1976-05-03 1977-06-21 Celanese Corporation Cationic polygalactomannan compositions
GB1572837A (en) * 1976-05-06 1980-08-06 Berger Jenson & Nicholson Ltd Coating composition
FR2357241B2 (en) 1976-07-08 1982-01-08 Oreal
LU75371A1 (en) 1976-07-12 1978-02-08
LU75370A1 (en) 1976-07-12 1978-02-08
US4152416A (en) 1976-09-17 1979-05-01 Marra Dorothea C Aerosol antiperspirant compositions delivering astringent salt with low mistiness and dustiness
US4128631A (en) 1977-02-16 1978-12-05 General Mills Chemicals, Inc. Method of imparting lubricity to keratinous substrates and mucous membranes
US4165367A (en) 1977-06-10 1979-08-21 Gaf Corporation Hair preparations containing vinyl pyrrolidone copolymer
CA1091160A (en) 1977-06-10 1980-12-09 Paritosh M. Chakrabarti Hair preparation containing vinyl pyrrolidone copolymer
US4223009A (en) 1977-06-10 1980-09-16 Gaf Corporation Hair preparation containing vinyl pyrrolidone copolymer
US4131576A (en) 1977-12-15 1978-12-26 National Starch And Chemical Corporation Process for the preparation of graft copolymers of a water soluble monomer and polysaccharide employing a two-phase reaction system
FR2439798B1 (en) 1978-10-27 1981-03-27 Oreal
US4296053A (en) * 1979-05-24 1981-10-20 Brown Group, Inc. Method of making foamed plastisol insoles for shoes
EP0062002B1 (en) * 1981-03-25 1986-06-04 Ciba-Geigy Ag Composition for fixing the hair, its preparation and its use in aerosol sprays
DE3273489D1 (en) 1981-11-30 1986-10-30 Ciba Geigy Ag Mixtures of quaternary polymeric acrylic ammonium salts, quaternary mono- or oligomeric ammonium salts and surfactants, their preparation and their use in cosmetic compositions
US4459249A (en) * 1982-01-22 1984-07-10 Inoue Mtp Kabushiki Kaisha Method of manufacturing a foamed protective and decorative molding for an automobile
US4524037A (en) * 1982-08-16 1985-06-18 Michel Marc Method and apparatus for forming a flexible thermoplastic resin foam article using an RF field
US4525231A (en) * 1983-06-08 1985-06-25 Voplex Corporation Method of making cushioned automotive strap handle
US4509949A (en) * 1983-06-13 1985-04-09 The B. F. Goodrich Company Water thickening agents consisting of copolymers of crosslinked acrylic acids and esters
US4514552A (en) 1984-08-23 1985-04-30 Desoto, Inc. Alkali soluble latex thickeners
US4592426A (en) * 1984-12-10 1986-06-03 Hughes Tool Company Upper termination with sliding sleeve seals
US4728571A (en) 1985-07-19 1988-03-01 Minnesota Mining And Manufacturing Company Polysiloxane-grafted copolymer release coating sheets and adhesive tapes
DE3677525D1 (en) 1985-08-12 1991-03-21 Allied Colloids Ltd polymeric thickening agents and their preparation.
US4693935A (en) 1986-05-19 1987-09-15 Minnesota Mining And Manufacturing Company Polysiloxane-grafted copolymer pressure sensitive adhesive composition and sheet materials coated therewith
JPH078505B2 (en) * 1986-07-30 1995-02-01 株式会社イノアックコ−ポレ−ション Method of manufacturing a plastic foam
FR2607373B1 (en) 1986-11-28 1989-02-24 Oreal Brush for applying mascara on the eyelashes
US5266321A (en) 1988-03-31 1993-11-30 Kobayashi Kose Co., Ltd. Oily make-up cosmetic comprising oil base and silicone gel composition
JPH0466446B2 (en) 1987-06-16 1992-10-23 Dow Corning Toray Silicone
LU87030A1 (en) 1987-10-28 1989-05-08 Oreal Use in cosmetics of new substances as reflectors of infrared radiation, cosmetic compositions containing them and their use for protecting the human epidermis against infrared radiation
EP0320218A3 (en) 1987-12-11 1990-04-25 THE PROCTER &amp; GAMBLE COMPANY Low glass transition temperature adhesive copolymers for use in hair styling products
US5061481A (en) 1989-03-20 1991-10-29 Kobayashi Kose Co., Ltd. Cosmetic composition having acryl-silicone graft copolymer
US5219560A (en) 1989-03-20 1993-06-15 Kobayashi Kose Co., Ltd. Cosmetic composition
US5156911A (en) 1989-05-11 1992-10-20 Landec Labs Inc. Skin-activated temperature-sensitive adhesive assemblies
DE69006556D1 (en) 1989-08-07 1994-03-24 Procter & Gamble Hair conditioning and hair styling agents.
EP0412704B1 (en) 1989-08-07 1999-04-28 THE PROCTER &amp; GAMBLE COMPANY Hair conditioning and styling compositions
US5209924A (en) * 1989-08-07 1993-05-11 Minnesota Mining And Manufacturing Company Polysiloxane-grafted copolymer topical binder composition with novel fluorochemical comonomer and method of coating therewith
US4981903A (en) * 1989-08-07 1991-01-01 Minnesota Mining And Manufacturing Company Polysiloxane-grafter copolymer topical binder composition with novel hydrophilic monomers and method of coating therewith
US4981902A (en) * 1989-08-07 1991-01-01 Minnesota Mining And Manufacturing Company Polysiloxane-grafted copolymer non-pressure sensitive topical binder composition and method of coating therewith
US4972037A (en) 1989-08-07 1990-11-20 Minnesota Mining And Manufacturing Company Polysiloxane-grafted copolymer topical binder composition with novel fluorochemical comonomer and method of coating therewith
FR2679444B1 (en) * 1991-07-25 1995-04-07 Oreal Use as thickening agents for oils, in an oily cosmetic composition, of a combination of two copolymers.
FR2685354B1 (en) 1991-12-24 1996-03-29 Rhone Poulenc Fibres Process for spinning solutions of polyamide-imides (PAI) based on toluylene diisocyanates or metaphenylene and fibers thus obtained.
US6258916B1 (en) 1991-12-24 2001-07-10 Rhone-Poulenc Fibres Process for spinning from solution of polyamide-imides (PAI) based on tolylene or meta-phenylene diisocyanates and fibers thus obtained
US5756635A (en) * 1991-12-24 1998-05-26 Rhone-Poulenc Fibres Process for spinning from solution of polyamide-imides (PAI) based on tolylene or met-phenylene diisocyanates and fibres thus obtained
JP3098604B2 (en) 1992-02-13 2000-10-16 株式会社コーセー Lipstick overcoat
ES2089822T3 (en) 1992-05-12 1996-10-01 Minnesota Mining & Mfg Polymers for cosmetics and personal care products.
US5468477A (en) 1992-05-12 1995-11-21 Minnesota Mining And Manufacturing Company Vinyl-silicone polymers in cosmetics and personal care products
CA2135186A1 (en) 1992-05-15 1993-11-25 Peter M. Torgerson Adhesive agent containing polysiloxane-grafted polymer, and cosmetic compositions thereof
DE4220807A1 (en) * 1992-06-25 1994-01-05 Basf Ag Vinyl polymers and produced in two-stage driving their use as paint binders
DE69332875T2 (en) 1992-07-28 2003-12-04 Mitsubishi Chem Corp A hair cosmetic composition
DE4225045A1 (en) 1992-07-29 1994-02-03 Basf Ag include use of water-soluble or water-dispersible polyurethanes as auxiliaries in cosmetic and pharmaceutical preparations and polyurethanes Polymilchsäurepolyole copolymerized form
JP3393903B2 (en) 1992-11-30 2003-04-07 株式会社資生堂 Makeup cosmetics
FR2701818B1 (en) * 1993-02-22 1995-06-16 Oreal Applicator.
US6663885B1 (en) * 1993-03-15 2003-12-16 A. Natterman & Cie Gmbh Aqueous liposome system and a method for the preparation of such a liposome system
JP3214674B2 (en) 1993-03-26 2001-10-02 出光興産株式会社 Novel styryl compounds, their production and an organic electroluminescence device comprising the same
EP0619111B2 (en) 1993-04-06 2005-09-14 National Starch and Chemical Investment Holding Corporation Use of polyurethanes with carboxylate functionality for hair fixative applications
US5374388A (en) * 1993-04-22 1994-12-20 Lockheed Corporation Method of forming contoured repair patches
US5476901A (en) 1993-06-24 1995-12-19 The Procter & Gamble Company Siloxane modified polyolefin copolymers
US5472798A (en) 1993-07-16 1995-12-05 Nissan Motor Co., Ltd. Coloring structure having reflecting and interfering functions
FR2708615B1 (en) 1993-08-04 1995-09-15 Oreal New polyester-polyurethanes, their preparation process, pseudo-latex produced from said polyester polyurethanes and their use in cosmetic compositions.
US6106813A (en) 1993-08-04 2000-08-22 L'oreal Polyester polyurethanes, process for preparing them, produced from the said polyester polyurethanes and their use in cosmetic compositions
EP0715638B1 (en) 1993-08-23 2000-05-24 THE PROCTER &amp; GAMBLE COMPANY Silicone grafted thermoplastic elastomeric copolymers and hair and skin care compositions containing the same
FR2710552B1 (en) 1993-09-30 1995-12-22 Lvmh Rech Use of acrylic block copolymers as wetting and / or dispersing solid particles and dispersions derived therefrom.
FR2710646B1 (en) * 1993-10-01 1995-12-22 Lvmh Rech stable microdispersions and microgels based on acrylic polymers, process for obtaining them and compositions, in particular cosmetic, containing them.
FR2711059B1 (en) 1993-10-15 1996-02-02 Oreal Cosmetic composition in the form of aqueous nail varnishes, colored or colorless, containing as film-forming substance of the anionic polyester-polyurethane particles in a dispersed state.
DE69426887D1 (en) * 1993-10-18 2001-04-19 Procter & Gamble Lipsticks, not sweat out the oil shares
JP3410189B2 (en) 1993-12-28 2003-05-26 株式会社コーセー Eye makeup cosmetics
FR2715063B1 (en) * 1994-01-17 1996-03-22 Oreal Cosmetic composition for makeup in the form of a mascara comprising at least one wax and a pseudo-latex of cellulose derivatives.
FR2715306B1 (en) 1994-01-25 1996-03-15 Oreal Cosmetic or dermopharmaceutical composition in the form of a soft paste and process for preparing said composition.
US6160054A (en) 1995-05-08 2000-12-12 Fmc Corporation Hetero-telechelic polymers and processes for making same
JPH07309721A (en) 1994-05-17 1995-11-28 Kao Corp Two-pack type nail-beautifying agent
JP3166482B2 (en) 1994-06-07 2001-05-14 日産自動車株式会社 Coloring structure having a reflection interference effects
FR2722380B1 (en) * 1994-07-12 1997-02-28
US6228967B1 (en) * 1996-05-22 2001-05-08 Mona Industries, Inc. Organosilicone having a carboxyl functional group thereon
FR2724843B1 (en) * 1994-09-28 1997-02-21
JPH08119836A (en) 1994-10-21 1996-05-14 Nippon Oil & Fats Co Ltd Cosmetic composition for nail
FR2727608B1 (en) 1994-12-06 1997-01-10 Oreal A dispenser for a liquid to pasty consistency of product
DE69533055D1 (en) 1994-12-06 2004-06-24 Oreal Dispenser for a liquid or pasty product having an application member
FR2727609B1 (en) 1994-12-06 1997-01-10 Oreal A dispensing assembly for applying a liquid product pasty consistency
US5686067A (en) 1995-01-05 1997-11-11 Isp Investments Inc. Low voc hair spray compositions
FR2733683B1 (en) 1995-05-05 1997-06-06 Oreal Nail varnish composition comprising a crosslinked polyester
US5747017A (en) * 1995-05-15 1998-05-05 Lip-Ink International Lip cosmetic
DE69605418D1 (en) 1995-06-15 2000-01-05 Raychem Ltd Gels made from triblockkopolymeren
US5969068A (en) * 1995-06-19 1999-10-19 The Lubrizol Corporation Dispersant-viscosity improvers for lubricating oil compositions
US5849275A (en) 1995-06-26 1998-12-15 Revlon Consumer Products Corporation Glossy transfer resistant cosmetic compositions
FR2736057B1 (en) 1995-06-27 1997-08-01 Oreal Polycondensates sequences polyurethanes and / or polyureas silicone grafts, cosmetic compositions containing them and uses
DE69625857T2 (en) 1995-06-30 2003-11-06 Chiba Flour Milling Silicone derivatives, their preparation and use
WO1997017057A1 (en) 1995-11-07 1997-05-15 The Procter & Gamble Company Compositions and methods for improving the performance of long-wearing cosmetic products
US6071503A (en) 1995-11-07 2000-06-06 The Procter & Gamble Company Transfer resistant cosmetic compositions
US5690918A (en) 1995-12-19 1997-11-25 Maybelline, Inc. Solvent-based non-drying lipstick
FR2743297B1 (en) 1996-01-05 1998-03-13 Oreal Cosmetic composition has basic ionizable polycondensates multiblock polysiloxane / polyurethane and / or polyurea in solution and use
FR2745174B1 (en) 1996-02-22 1998-04-30 Oreal Cosmetic composition for fixing and brilliance
JP3605938B2 (en) 1996-03-29 2004-12-22 株式会社コーセー Eyelash cosmetic
US5849318A (en) 1996-06-26 1998-12-15 Kao Corporation Oil-based solid cosmetic composition
DE19638795A1 (en) * 1996-09-20 1998-03-26 Basf Ag Aqueous or aqueous / alcoholic hair cosmetic formulation
US5783657A (en) 1996-10-18 1998-07-21 Union Camp Corporation Ester-terminated polyamides of polymerized fatty acids useful in formulating transparent gels in low polarity liquids
JP3814032B2 (en) * 1996-11-01 2006-08-23 チッソ株式会社 Molding
CA2220033A1 (en) 1996-11-26 1998-05-26 L'oreal Non-transfer topical composition containing a fluorinated or silicone compound and offering improved comfort, its use
FR2756176B1 (en) 1996-11-26 1998-12-18 Oreal Cosmetic composition comprising a fluorinated compound and having improved comfort
FR2758083B1 (en) 1997-01-03 1999-02-05 Oreal Cosmetic and / or dermatological composition containing a dispersion of a polymer system and using this system as tensor
US5736125A (en) * 1997-01-10 1998-04-07 National Starch And Chemical Investment Holding Corporation Compositions containing copolymers as a thickening agent
CA2249478A1 (en) 1997-01-20 1998-07-23 L'oreal Cosmetic composition containing as coating agent keratinous fibre a film-forming mixture consisting of polymer particles capable of being film-formed and particles not capable of being film-formed
US6140431A (en) 1997-02-27 2000-10-31 Rohm And Haas Company Process for preparing continuously variable-composition copolymers
US6433068B1 (en) 1997-03-07 2002-08-13 David S. Morrison Hydrocarbon gels as suspending and dispersing agents and products
JP4149522B2 (en) * 1997-03-26 2008-09-10 エイヴォン プロダクツ,インク. Wear-resistant cosmetics
US6303105B1 (en) 1997-03-26 2001-10-16 Avon Products, Inc. Cosmetic composition for imparting wear resistance and shine
US6267951B1 (en) 1997-03-26 2001-07-31 Avon Products, Inc. Cosmetic composition for the nails and hair
US5879670A (en) 1997-03-31 1999-03-09 Calgon Corporation Ampholyte polymers for use in personal care products
FR2761959B1 (en) * 1997-04-15 1999-05-21 Oreal Packaging assembly and applying a fluid
US6165457A (en) 1997-05-12 2000-12-26 The Procter & Gamble Company Personal care compositions containing toughened grafted polymers
DE69839333T2 (en) 1997-05-30 2009-07-09 Shiseido Co. Ltd. A copolymer composition containing the silyl group-having reactive and process for use
US6153206A (en) * 1997-08-27 2000-11-28 Revlon Consumer Products Corporation Cosmetic compositions
JPH11100307A (en) 1997-09-29 1999-04-13 Kao Corp Film-forming agent and cosmetic
JPH11124312A (en) 1997-10-20 1999-05-11 Shiseido Co Ltd Pack cosmetic and its treatment
FR2774587B1 (en) 1998-02-09 2000-03-10 Oreal Utilization of a wax microdispersion in a cosmetic or dermatological composition
FR2774588B1 (en) * 1998-02-11 2000-05-05 Oreal Cosmetic or dermatological composition containing at least one protein of natural spider silk, recombinant or an analogue
FR2775566B1 (en) 1998-03-03 2000-05-12 Oreal Stick-carrying cup and packaging assembly for a makeup product having the
FR2775593B1 (en) 1998-03-09 2002-06-14 Oreal film-forming composition comprising a polyurethane aqueous dispersion and a plasticizer
FR2776509B1 (en) 1998-03-31 2001-08-10 Oreal Topical composition containing a fatty acid ester or alcohol branched C24 to c28
EP0951897B1 (en) * 1998-04-21 2003-09-03 L'oreal Topical composition containing an olefinic copolymer with controlled crystallisation
US6225390B1 (en) * 1998-05-08 2001-05-01 Shell Oil Company Oil gel formulations containing polystyrene-polydimethylsiloxane or polyethylene-polydimethylsiloxane block copolymers dissolved in siloxane monomers
CA2276568C (en) * 1998-07-03 2007-01-02 Kuraray Co., Ltd. Block copolymer and polymer composition comprising the same
FR2782003B1 (en) 1998-08-10 2000-10-13 Oreal makeup composition or transfer without basic care has isoparaffins and synthetic waxes FUNCTIONALISED
US6068421A (en) 1998-08-25 2000-05-30 Rexam Cosmetic Packaging, Inc. Protective shell for a cosmetic container
US6881776B2 (en) * 1998-10-29 2005-04-19 Penreco Gel compositions
WO2000026285A1 (en) 1998-10-29 2000-05-11 Penreco Gel compositions
WO2000028948A1 (en) 1998-11-12 2000-05-25 The Procter & Gamble Company Cosmetic compositions
US6268466B1 (en) 1999-01-04 2001-07-31 Arizona Chemical Company Tertiary amide terminated polyamides and uses thereof
DE19903391A1 (en) 1999-01-29 2000-08-03 Bayer Ag An aqueous coating medium, process for its preparation and its use
US6423306B2 (en) 1999-02-26 2002-07-23 L'oreal Sa Cosmetic compositions containing di-block, tri-block, multi-block and radial block copolymers
FR2791042B1 (en) 1999-03-16 2001-05-04 Oreal articulated assembly PIECE
DE60042645D1 (en) 1999-03-18 2009-09-10 California Inst Of Techn New aba triblock and diblock copolymers and methods for their preparation
FR2791987A1 (en) 1999-04-06 2000-10-13 Oreal In particular cosmetic composition comprising polymers having a star structure, said polymers and their use
FR2792190B1 (en) 1999-04-16 2001-09-28 Sophim Method of manufacturing a non-greasy emollient wax-based esters
FR2792618B1 (en) 1999-04-23 2001-06-08 Oreal Device for packaging and applying a product having a wiper member comprising a slot
US6197883B1 (en) * 1999-06-03 2001-03-06 Ppg Industries Ohio, Inc. Thermosetting coating compositions containing flow modifiers prepared by controlled radical polymerization
US6254878B1 (en) 1999-07-01 2001-07-03 E. I. Du Pont De Nemours And Company Nail polish compositions containing acrylic polymers
FR2795957B1 (en) 1999-07-08 2001-09-28 Oreal makeup composition comprising fibers
JP2003520063A (en) 1999-07-09 2003-07-02 ブルジヨワ Related articles and a method of manufacturing the topical composition
FR2796272B1 (en) 1999-07-15 2003-09-19 Oreal Composition without wax structured hard form a polymer
EP1115303B1 (en) * 1999-07-21 2014-10-08 L'Oréal Device for applying a product on keratinous fibres
FR2796528B1 (en) 1999-07-21 2001-09-21 Oreal packaging and applicator device of a substance to the eyelashes or the eyebrows
FR2796529B1 (en) 1999-07-21 2001-09-21 Oreal packaging and applicator device of a substance to the eyelashes or the eyebrows
DE19939326A1 (en) 1999-08-19 2001-02-22 Basf Ag Aqueous cosmetic composition, e.g. nail varnish or hair setting lotion, contains an emulsion polymer with a glass transition point above room temperature and a minimum film-forming temperature below this
US6174968B1 (en) * 1999-08-24 2001-01-16 Shell Oil Company Oil gel formulations containing polysiloxane block copolymers dissolved in hydrogenated silicone oils
FR2798061A1 (en) 1999-09-07 2001-03-09 Oreal cosmetic composition comprising polymer dispersions of particles in a liquid fatty phase
US7101928B1 (en) 1999-09-17 2006-09-05 Landec Corporation Polymeric thickeners for oil-containing compositions
US6124490A (en) 1999-10-26 2000-09-26 Mona Industries, Inc. Zwitterionic siloxane polymers and ionically cross-linked polymers formed therefrom
US6309629B1 (en) 1999-12-14 2001-10-30 Avon Products, Inc. Wear resistant cosmetic compositions
EP1112735A1 (en) * 1999-12-20 2001-07-04 Avon Products, Inc. Cosmetic composition applied to the eyelashes
FR2803743B1 (en) * 2000-01-14 2005-04-15 Atofina cosmetic compositions containing aqueous polymer dispersions, film-forming in the absence of organic solvent
FR2806273B1 (en) 2000-03-16 2002-10-04 Oreal packaging and applicator device of a cosmetic or care product
US20020018759A1 (en) * 2000-05-04 2002-02-14 Pagano Frank Charles Nail enamel compositions, related methods, and a two component kit for painting the nails
DE10022247A1 (en) 2000-05-08 2001-11-15 Basf Ag Polyurethane used as rheology-modifier e.g. in cosmetics or pharmaceuticals, based on di-isocyanate, polyether-polyol and long-chain mono-alcohol, -thiol or -amine
FR2809306B1 (en) 2000-05-23 2004-02-06 Oreal Cosmetic use of block ethylenic copolymers of elastic nature and compositions containing
JP4768103B2 (en) 2000-06-06 2011-09-07 日東電工株式会社 Its adhesive sheet and a pressure-sensitive adhesive composition - DOO acids and processes for their preparation
FR2810237B1 (en) 2000-06-15 2002-07-26 Oreal Film-forming cosmetic composition
US6423304B1 (en) 2000-06-15 2002-07-23 Cognis Corporation Dimerized fatty acid based polyamides useful for clear candle and gel applications
DE10029697A1 (en) 2000-06-16 2001-12-20 Basf Ag Binding composition, useful e.g. in paints and inks, or for pigmentation, comprises radical-polymerized block copolymer and non-magnetic filler
FR2811546B1 (en) 2000-07-13 2003-09-26 Oreal Kit and long-wearing makeup process
FR2811885B1 (en) * 2000-07-18 2003-06-06 Oreal Cosmetic composition containing a block copolymer is a sequence has different refractive indices
FR2811993B1 (en) 2000-07-21 2006-08-04 Oreal New cationic associative polymers and their use as thickeners
US6518364B2 (en) 2000-09-28 2003-02-11 Symyx Technologies, Inc. Emulsion living-type free radical polymerization, methods and products of same
FR2814365B1 (en) * 2000-09-28 2002-12-27 Oreal cosmetic composition comprising at least one liquid fatty phase structured with polyurethanes and / or polyureas
FR2814673B1 (en) 2000-09-29 2003-04-11 Oreal Film-forming cosmetic composition
EP1322279A1 (en) * 2000-10-03 2003-07-02 Unilever N.V. Cosmetic and personal care compositions
DE60132819D1 (en) 2000-10-25 2008-03-27 3M Innovative Properties Co Use of copolymer to acrylic base in cosmetics and for personal hygiene
US20020076390A1 (en) 2000-10-25 2002-06-20 3M Innovative Properties Company Acrylic-based copolymer compositions for cosmetic and personal care
FR2815847B1 (en) 2000-10-27 2002-12-13 Oreal cosmetic composition comprising fibers and wax
FR2816503B1 (en) 2000-11-10 2003-03-28 Oreal Cosmetic composition structured by a thermotropic liquid crystal polymer
DE10059831A1 (en) * 2000-12-01 2002-06-13 Clariant Gmbh Silicon-modified comb polymers based on acryloyidimethyltaurine
DE10059825A1 (en) * 2000-12-01 2002-06-13 Clariant Gmbh Use of comb-shaped copolymers based on acryloyldimethyltaurine in cosmetic, pharmaceutical and dermatological compositions
DE10059821A1 (en) * 2000-12-01 2002-06-13 Clariant Gmbh Surfactant cosmetic, dermatological and pharmaceutical compositions
DE10059818A1 (en) 2000-12-01 2002-06-13 Clariant Gmbh Decorative cosmetic and dermatological
DE10059819A1 (en) 2000-12-01 2002-06-13 Clariant Gmbh Surfactant-containing cosmetic, dermatological and pharmaceutical compositions
DE10059832A1 (en) * 2000-12-01 2002-06-13 Clariant Gmbh Graft copolymers based on acryloyldimethyltaurine
DE10059822A1 (en) 2000-12-01 2002-06-13 Clariant Gmbh Acidic cosmetic, pharmaceutical and dermatological compositions
DE10059827A1 (en) 2000-12-01 2002-06-20 Clariant Gmbh Cosmetic and dermatological hair treatment agent
DE10059829A1 (en) 2000-12-01 2002-06-13 Clariant Gmbh Grafted comb polymers based on acryloyidimethyltaurine
DE10059826A1 (en) 2000-12-01 2002-06-13 Clariant Gmbh Cosmetic, pharmaceutical and dermatological compositions
DE10059828A1 (en) * 2000-12-01 2002-06-13 Clariant Gmbh Comb-shaped copolymers based on acryloyldimethyltaurine
DE10059824A1 (en) * 2000-12-01 2002-06-13 Clariant Gmbh Electrolyte-containing cosmetic, pharmaceutical and dermatological compositions
DE10059830A1 (en) 2000-12-01 2002-06-13 Clariant Gmbh Cationic modified comb polymers based on acryloyidimethyltaurine
JP2002327102A (en) * 2000-12-01 2002-11-15 Clariant Gmbh Composition containing copolymer based on acryloyldimethyltaurine acid and synergistic additive
DE10059823A1 (en) * 2000-12-01 2002-06-13 Clariant Gmbh Deodorants and antiperspirants
DE10059833A1 (en) 2000-12-01 2002-06-13 Clariant Gmbh Fluorine-modified comb polymers based on Acryloyldimethylaurinsäure
JP2002201244A (en) 2000-12-28 2002-07-19 Nippon Shokubai Co Ltd Acrylic block copolymer, composition for vibration- damping material, and production method for acrylic block copolymer
US20020159960A1 (en) 2001-02-27 2002-10-31 Scancarella Neil D. Method for improving the properties of transfer resistant lip compositions and related compositions and articles
FR2822698B1 (en) * 2001-04-03 2006-04-21 Oreal New dye composition for dyeing keratin fibers comprising a monoazo dye dicationic
FR2823103B1 (en) 2001-04-10 2003-05-23 Oreal coat makeup product containing a goniochromatic pigment and a monochromatic pigment and makeup kit containing this product
US20030039621A1 (en) * 2001-04-10 2003-02-27 L'oreal Two-coat make-up product, its use and a kit containing the make-up product
FR2823101B1 (en) 2001-04-10 2004-02-06 Oreal bilayer makeup product, its uses and makeup kit containing product
CN1280157C (en) 2001-08-21 2006-10-18 美国莱雅公司 Beauty box with virtual hinge
FR2824267B1 (en) * 2001-05-04 2008-06-27 Oreal Film-forming cosmetic composition
JP4666442B2 (en) 2001-07-27 2011-04-06 株式会社吉野工業所 Shock-absorbing container
US20030024074A1 (en) * 2001-08-01 2003-02-06 Hartman Paul H. Biconcave connector for tubular assemblies and tool handles
WO2003024414A1 (en) 2001-09-13 2003-03-27 Mitsubishi Chemical Corporation Resin compositions for cosmetics and cosmetics
JP4039829B2 (en) 2001-09-13 2008-01-30 三菱化学株式会社 Cosmetic resin composition and a cosmetic using the same
FR2831430B1 (en) 2001-10-26 2004-02-06 Oreal Cosmetic composition and / or care containing a film-forming polyester-siloxane, uncrosslinked
FR2832720B1 (en) * 2001-11-29 2004-02-13 Oreal Ethylenic copolymers sequences, cosmetic compositions containing them, and use of these copolymers in cosmetic
FR2832719B1 (en) * 2001-11-29 2004-02-13 Oreal Block ethylenic copolymers adhesives, cosmetic compositions containing them and use of these copolymers in cosmetic
EP1448646A2 (en) 2001-11-29 2004-08-25 L'oreal Adhesive block ethylene copolymers, cosmetic compositions containing same, and use thereof in cosmetics
FR2834458A1 (en) 2002-01-08 2003-07-11 Oreal Composition especially useful as nail varnish comprises two film-forming polymers with high and low glass transition temperatures dispersed as solid particles in an aqueous medium
JP2003286142A (en) 2002-03-29 2003-10-07 Mitsubishi Chemicals Corp Polymer composition for hair cosmetic and the resulting hair cosmetic
US20030185774A1 (en) 2002-04-02 2003-10-02 Dobbs Suzanne Winegar Cosmetic coating composition comprising carboxyalkyl cellulose ester
FR2840205B1 (en) 2002-05-31 2005-08-05 Oreal Shampoos containing at least one amphiphilic block copolymer and at least one cationic or amphoteric polymer
US7176170B2 (en) 2002-05-31 2007-02-13 L'oreal Shampoo comprising at least one silicone and at least one anionic or nonionic, amphiphilic linear block copolymer
FR2840209B1 (en) 2002-05-31 2005-09-16 Oreal capillary aqueous composition thickened by a copolymer amphiphilic linear sequence
FR2840206B1 (en) 2002-05-31 2005-08-05 Oreal Shampoo containing at least one silicone and at least one amphiphilic copolymer linear sequence, anionic or nonionic
FR2842417B1 (en) 2002-07-19 2005-01-21 Oreal cosmetic Composition
US7008629B2 (en) * 2002-07-22 2006-03-07 L'ORéAL S.A. Compositions comprising at least one heteropolymer and fibers, and methods of using the same
US7923002B2 (en) 2002-09-06 2011-04-12 L'oreal S.A. Composition for coating keratin fibres comprising a tacky wax
DE60330571D1 (en) 2002-09-06 2010-01-28 Oreal Makeup for keratin fibers, in particular for batting
DE60305847T2 (en) 2002-09-06 2006-12-14 L'oreal Cosmetic composition containing a tacky wax
US20060099231A1 (en) 2002-09-06 2006-05-11 De La Poterie Valerie Make-up composition for keratin fibres such as eyelashes
US7687510B2 (en) 2002-09-10 2010-03-30 Bayer Healthcare Ag Pyrimidinone derivatives as therapeutic agents against acute and chronic inflammatory, ischaemic and remodelling processes
FR2844709A1 (en) 2002-09-20 2004-03-26 Oreal Plastic, thixotropic composition, preferably for make-up or care of keratin fibers, especially mascara, containing film-forming polymer or wax and rigid, rectilinear fibers to ensure homogeneous deposition
US20060128578A9 (en) 2002-09-20 2006-06-15 Nathalie Jager Lezer Cosmetic composition comprising rigid fibres and at least one compound chosen from film-forming polymers and waxes
US6905696B2 (en) 2003-01-06 2005-06-14 Color Access, Inc. Alignment of enhancers in cosmetic compositions
FR2860156B1 (en) 2003-09-26 2007-11-02 Oreal Cosmetic composition comprising a tensioning agent and a polymer ethylenically particular sequence
FR2860142B1 (en) 2003-09-26 2007-08-17 Oreal bilayer cosmetic product, its uses and makeup kit containing product
FR2864896B1 (en) * 2004-01-13 2006-03-31 Oreal composition for coating keratin fibers, comprising a block polymer and a semicrystalline polymer
FR2864894A1 (en) * 2004-01-13 2005-07-15 Oreal Easily applied keratin fiber coating composition, especially mascara, containing film-forming linear sequenced ethylenic polymer and fibers
US20050220731A1 (en) * 2004-03-23 2005-10-06 Philippe Ilekti Nail varnish composition comprising at least one polymer and at least one plasticizer
DE102004014806B4 (en) * 2004-03-24 2006-09-14 Daimlerchrysler Ag Rapid technology component
US8728451B2 (en) 2004-03-25 2014-05-20 L'oreal Styling composition comprising, in a predominantly aqueous medium, a pseudo-block polymer, processes employing same and uses thereof
US20050287103A1 (en) 2004-06-08 2005-12-29 Vanina Filippi Cosmetic composition comprising at least one ester and at least one film-forming polymer
FR2871057B1 (en) 2004-06-08 2006-07-28 Oreal Cosmetic composition containing an ester and a film-forming agent
FR2876011B1 (en) 2004-10-05 2006-12-29 Oreal Method makeup of a support and kit for the implementation of such process
JP2006151867A (en) 2004-11-29 2006-06-15 Rohto Pharmaceut Co Ltd Solid lip gloss
FR2880268B1 (en) 2005-01-05 2008-10-24 Oreal gloss composition and not transfer comprising two polymer blocks
US20070134181A1 (en) 2005-12-08 2007-06-14 L'oreal Cosmetic composition comprising an ester of dimerdilinoleic acid and of polyol(s) and a silicone surfactant
FR2904320B1 (en) * 2006-07-27 2008-09-05 Oreal Polymers sequences, and their method of preparing
FR2904218B1 (en) * 2006-07-27 2012-10-05 Oreal Cosmetic composition combining a copolymer, a non-volatile oil and a glossy oil.
WO2009080958A3 (en) 2007-12-05 2010-04-22 L'oreal Cosmetic make-up and/or care method using a siloxane resin and an organopolysiloxane elastomer
ES2645387T3 (en) 2009-06-01 2017-12-05 L'oréal Cosmetic composition comprising a block polymer and a non-volatile ester oil
GB0922457D0 (en) 2009-12-23 2010-02-03 Parry Mark GPS enabled software that appraises surfing performance on a mobile device
US9192561B2 (en) 2010-05-14 2015-11-24 L'oreal Compositions containing hyperbranched polyol and acrylic film former
US8586013B2 (en) 2010-12-30 2013-11-19 L'oreal Comfortable, long-wearing, transfer-resistant colored cosmetic compositions having a non-tacky feel
US20120171139A1 (en) 2010-12-30 2012-07-05 L'oreal S.A. Comfortable, long-wearing, transfer-resistant colored cosmetic compositions

Patent Citations (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4425326A (en) * 1980-04-01 1984-01-10 Societe Anonyme Dite : L'oreal Anhydrous nail varnishes
US6692733B1 (en) * 1999-04-06 2004-02-17 L'oreal Composition comprising polymers having a star structure, the polymers, and their use
US6410005B1 (en) * 2000-06-15 2002-06-25 Pmd Holdings Corp. Branched/block copolymers for treatment of keratinous substrates
US20030059392A1 (en) * 2001-07-18 2003-03-27 L'oreal Composition for topical use containing a diblock polymer
US20040009136A1 (en) * 2002-05-31 2004-01-15 L'oreal Aqueous hair treatment compositions, thickened with an amphiphilic linear block copolymer
US20040039101A1 (en) * 2002-05-31 2004-02-26 Claude Dubief Washing compositions comprising at least one amphiphilic block copolymer and at least one cationic or amphoteric polymer
US20040077788A1 (en) * 2002-07-19 2004-04-22 Cid Centro De Investigacion Y Desarrollo Tecnologico, S.A. De. C.V. Block copolymers containing functional groups
US20040120920A1 (en) * 2002-09-26 2004-06-24 Bertrand Lion Novel block polymers and cosmetic compositions and processes comprising them
US20040120906A1 (en) * 2002-09-26 2004-06-24 Beatrice Toumi Nail varnish composition comprising a block polymer
US20060134051A1 (en) * 2002-09-26 2006-06-22 Xavier Blin Glossy non-transfer composition comprising a sequenced polymer
US20060093568A1 (en) * 2002-09-26 2006-05-04 Xavier Blin Composition comprising a block polymer and a film-forming agent
US20060127334A1 (en) * 2002-09-26 2006-06-15 Veronique Ferrari Lipstick comprising a sequenced polymer
US20060147402A1 (en) * 2002-09-26 2006-07-06 Xavier Blin Composition comprising a sequenced polymer and a gelling agent
US20050106197A1 (en) * 2003-09-26 2005-05-19 Xavier Blin Cosmetic composition comprising a block polymer and a non-volatile silicone oil

Cited By (28)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7875265B2 (en) * 2002-09-26 2011-01-25 L'oreal Cosmetic composition comprising a sequenced polymer and a plasticizer
US9017704B2 (en) 2002-09-26 2015-04-28 L'oreal Composition comprising a block polymer and a film-forming agent
US8992903B2 (en) 2002-09-26 2015-03-31 L'oreal Composition comprising at least one block polymer and at least one gelling agent
US20040120906A1 (en) * 2002-09-26 2004-06-24 Beatrice Toumi Nail varnish composition comprising a block polymer
US20080014234A1 (en) * 2002-09-26 2008-01-17 L'oreal Novel Block Polymers and Cosmetic Compositions and Processes Comprising Them
US20080014158A1 (en) * 2002-09-26 2008-01-17 L'oreal Novel Block Polymers and Cosmetic Compositions and Processes Comprising Them
US20080014235A1 (en) * 2002-09-26 2008-01-17 L'oreal Novel Block Polymers and Cosmetic Compositions and Processes Comprising Them
US7932324B2 (en) 2002-09-26 2011-04-26 L'oreal Block polymers and cosmetic compositions and processes comprising them
US7915347B2 (en) 2002-09-26 2011-03-29 L'oreal S.A. Block polymers and cosmetic compositions and processes comprising them
US7803877B2 (en) 2002-09-26 2010-09-28 L'oreal S.A. Block polymers and cosmetic compositions and processes comprising them
US8119110B2 (en) 2003-09-26 2012-02-21 L'oreal S.A. Cosmetic composition comprising a block polymer and a non-volatile silicone oil
US20050220731A1 (en) * 2004-03-23 2005-10-06 Philippe Ilekti Nail varnish composition comprising at least one polymer and at least one plasticizer
US8728451B2 (en) * 2004-03-25 2014-05-20 L'oreal Styling composition comprising, in a predominantly aqueous medium, a pseudo-block polymer, processes employing same and uses thereof
US20050220747A1 (en) * 2004-03-25 2005-10-06 Bertrand Lion Styling composition comprising, in a predominantly aqueous medium, a pseudo-block polymer, processes employing same and uses thereof
US8460645B2 (en) 2005-07-22 2013-06-11 L'oreal S.A. Process for coating eyelashes
US20070196306A1 (en) * 2005-07-22 2007-08-23 Nathalie Jager Lezer Process for coating eyelashes
US8710152B2 (en) 2006-07-27 2014-04-29 L'oreal Block polymers and their process of preparation
US20080145325A1 (en) * 2006-09-13 2008-06-19 Lizabeth-Anne Coffey-Dawe Nail varnish comprising at least one resin
US20100215605A1 (en) * 2008-11-24 2010-08-26 L'oreal Solid cosmetic composition for application to keratin fibres
US20110020263A1 (en) * 2009-06-01 2011-01-27 L'oreal Composition containing a block polymer and a nonvolatile ester oil
US9895561B2 (en) 2009-06-01 2018-02-20 L'oreal Composition containing a block polymer and a nonvolatile ester oil
US20120118314A1 (en) * 2009-07-21 2012-05-17 Danny Lee Haile Compositions for removable gel applications for nails and methods of their use
US9023326B2 (en) * 2009-07-21 2015-05-05 Nail Alliance Llc Compositions for removable gel applications for nails and methods of their use
US9526686B2 (en) 2009-07-21 2016-12-27 Nail Alliance, Llc Compositions for removable gel applications for nails and methods of their use
US20120199151A1 (en) * 2009-07-21 2012-08-09 Danny Lee Haile Compositions for removable gel applications for nails and methods of their use
US9125468B2 (en) 2010-03-29 2015-09-08 L'oreal Device for the application of fibers to human keratinous fibers
US20130213426A1 (en) * 2010-11-02 2013-08-22 L'oreal Two-step nail polish product
US20170360683A1 (en) * 2016-06-15 2017-12-21 Mycone Dental Supply Co., Inc. One Part Acrylic Nail Formulation

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