WO2005060922A1 - Composition cosmetique contenant un polymere polyorganosiloxane - Google Patents

Composition cosmetique contenant un polymere polyorganosiloxane Download PDF

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Publication number
WO2005060922A1
WO2005060922A1 PCT/US2003/039502 US0339502W WO2005060922A1 WO 2005060922 A1 WO2005060922 A1 WO 2005060922A1 US 0339502 W US0339502 W US 0339502W WO 2005060922 A1 WO2005060922 A1 WO 2005060922A1
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WIPO (PCT)
Prior art keywords
composition
groups
silicone
chosen
formula
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PCT/US2003/039502
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English (en)
Inventor
Veronique Ferrari
Florence Tournilhac
Wei Yu
Shao Xiang Lu
Xavier Blin
Jean Mondet
Isabelle Hansenne
Anil Shah
Angelike Galdi
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L'oreal
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Priority to PCT/US2003/039502 priority Critical patent/WO2005060922A1/fr
Priority to AU2003297905A priority patent/AU2003297905A1/en
Publication of WO2005060922A1 publication Critical patent/WO2005060922A1/fr

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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A61K8/89—Polysiloxanes
    • A61K8/896—Polysiloxanes containing atoms other than silicon, carbon, oxygen and hydrogen, e.g. dimethicone copolyol phosphate
    • A61K8/898—Polysiloxanes containing atoms other than silicon, carbon, oxygen and hydrogen, e.g. dimethicone copolyol phosphate containing nitrogen, e.g. amodimethicone, trimethyl silyl amodimethicone or dimethicone propyl PG-betaine
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/74—Synthetic polymeric materials
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/31—Hydrocarbons
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A61K8/89—Polysiloxanes
    • A61K8/891—Polysiloxanes saturated, e.g. dimethicone, phenyl trimethicone, C24-C28 methicone or stearyl dimethicone
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A61K8/89—Polysiloxanes
    • A61K8/891—Polysiloxanes saturated, e.g. dimethicone, phenyl trimethicone, C24-C28 methicone or stearyl dimethicone
    • A61K8/894—Polysiloxanes saturated, e.g. dimethicone, phenyl trimethicone, C24-C28 methicone or stearyl dimethicone modified by a polyoxyalkylene group, e.g. cetyl dimethicone copolyol
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q1/00—Make-up preparations; Body powders; Preparations for removing make-up
    • A61Q1/02—Preparations containing skin colorants, e.g. pigments
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q1/00—Make-up preparations; Body powders; Preparations for removing make-up
    • A61Q1/02—Preparations containing skin colorants, e.g. pigments
    • A61Q1/04—Preparations containing skin colorants, e.g. pigments for lips
    • A61Q1/06—Lipsticks
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q1/00—Make-up preparations; Body powders; Preparations for removing make-up
    • A61Q1/02—Preparations containing skin colorants, e.g. pigments
    • A61Q1/10—Preparations containing skin colorants, e.g. pigments for eyes, e.g. eyeliner, mascara

Definitions

  • compositions for example, a transfer resistant cosmetic composition, which may also be pliable and/or comfortable to wear upon application to a eratinous substrate, comprising at least one polyorganosiloxane containing polymer comprising at least one moiety comprising: at least one polyorganosiloxane group comprising organosiloxane units in the chain of the moiety or in the form of a graft, and at least two groups capable of establishing hydrogen interactions, and which composition is free of silicone oils.
  • a transfer resistant cosmetic composition which may also be pliable and/or comfortable to wear upon application to a eratinous substrate, comprising at least one polyorganosiloxane containing polymer comprising at least one moiety comprising: at least one polyorganosiloxane group comprising organosiloxane units in the chain of the moiety or in the form of a graft, and at least two groups capable of establishing hydrogen interactions, and which composition is free of silicone oils.
  • compositions including pigmented cosmetics such as foundations, concealers, lipsticks, mascaras, and other cosmetic and sunscreen compositions have been developed for longer wear and transfer resistance properties. This is accomplished by the use of compositions that form a film after application.
  • Such compositions generally contain volatile solvents, which evaporate on contact with the skin or other keratinous tissue, leaving behind a layer comprising waxes and/or resins, pigments, fillers, and actives.
  • these compositions tend to be uncomfortable for the wearer as the composition remains on the skin or other keratinous tissue as a brittle or non-flexible film.
  • Such compositions may not be pliable or soft, and they may not be comfortable to wear.
  • Document EP-A-1 068 856 describes wax-free solid cosmetic compositions, comprising a liquid fatty phase structured with a polymer, in which the fatty phase is primarily a non-silicone oil.
  • cosmetic compositions such as deodorant gels or sticks, are prepared. These compositions comprise a silicone oily phase gelled with a wax based on polysiloxane and polyamide, or with a polymer comprising siloxane groups and groups capable of hydrogen interactions. [006] When these cosmetic compositions are used as deodorants, the problems of migration of the oily phase into wrinkles and fine lines, and the problems of the staying power and transfer resistance of the composition are not significant.
  • a composition that is transfer resistant may deposit a film onto a keratinous substance that may not transfer when the keratinous substance comes into contact with, for example, skin, clothes, a cup, paper, cigarette, or a handkerchief.
  • the present inventors have surprisingly discovered that the at least one polyorganosiloxane containing polymer can be formulated into a composition which is free of silicone oils.
  • one aspect of the present invention is a care and/or makeup and/or treatment composition for keratinous material such as the skin and/or the lips, which is able to address or overcome at least one of the aforementioned problems with the prior art compositions.
  • the present invention relates to compositions, preferably cosmetic compositions, which are substantially free of, devoid of or free of silicone oils, comprising at least one polyorganosiloxane containing polymer chosen from homopolymers and copolymers as well as to methods for treating, caring for and/or making up keratinous material by applying such compositions to the keratinous material.
  • the present invention also relates to cosmetic compositions, which are substantially free of, devoid of or free of silicone oils, comprising at least one polyorganosiloxane containing polymer, preferably a polysilicone-polyamide copolymer, and at least one non-silicone volatile oil, such as a hydrocarbon volatile oil.
  • the present invention also relates to cosmetic compositions, which are substantially free of, devoid of or free of silicone oils, comprising at least one polyorganosiloxane containing polymer, preferably a polysilicone-polyamide copolymer, and at least one film forming agent.
  • the present invention also relates to cosmetic compositions, which are substantially free of, devoid of or free of silicone oils, comprising at least one polyorganosiloxane containing polymer, preferably a polysilicone-polyamide copolymer, at least one silicone film forming agent, and at least one non-silicone volatile oil, such as a hydrocarbon volatile oil.
  • the present invention also relates to colored cosmetic compositions, which are substantially free of, devoid of or free of silicone oils, comprising at least one polyorganosiloxane containing polymer, preferably a silicone-polyamide copolymer.
  • such colored cosmetic compositions are anhydrous lip compositions (for example, lipstick or liquid lip colors) or foundations.
  • the present invention further relates to colored cosmetic compositions, which are substantially free of, devoid of or free of silicone oils, comprising at least one polyorganosiloxane containing polymer, preferably a silicone-polyamide copolymer, and water.
  • such water-containing colored cosmetic compositions are lip compositions (for example, lipstick or liquid lip colors), foundations or mascaras, and are emulsions or dispersions.
  • the present invention also relates to methods of treating, caring for and/or making up keratinous material (for example, skin) by applying compositions of the present invention to the keratinous material in an amount sufficient to treat, care for and/or make up the keratinous material.
  • the present invention further relates to covering or hiding skin defects associated with keratinous material (for example, skin) by applying compositions of the present invention to the keratinous material in an amount sufficient to cover or hide such skin defects.
  • the present invention also relates to methods of enhancing the appearance of keratinous material (for example, skin) by applying compositions of the present invention to the keratinous material in an amount sufficient to enhance the appearance of the keratinous material.
  • the present invention further relates to compositions having improved cosmetic properties such as, for example, improved long wear, transfer resistance and/or waterproof properties.
  • the compositions may also possess improved flexibility, wearability, drying time and/or retention as well as reduced tackiness and/or migration over time.
  • the expression “at least one” means one or more and thus includes individual components as well as mixtures/combinations.
  • "Film former” or “film forming agent” as used herein means a polymer that, after dissolution in at least one solvent (such as, for example, water and organic solvents), leaves a film on the substrate to which it is applied, for example, once the at least one solvent evaporates, absorbs and/or dissipates on the substrate.
  • solvent such as, for example, water and organic solvents
  • Transfer resistance refers to the quality exhibited by compositions that are not readily removed by contact with another material, such as, for example, a glass, an item of clothing or the skin, for example, when eating or drinking. Transfer resistance may be evaluated by any method known in the art for evaluating such. For example, transfer resistance of a composition may be evaluated by a "kiss” test. The "kiss” test may involve application of the composition to human lips followed by "kissing" a material, for example, a sheet of paper, after expiration of a certain amount of time following application, such as 2 minutes after application.
  • transfer resistance of a composition may be evaluated by the amount of product transferred from a wearer to any other substrate, such as transfer from the neck of an individual to a collar after the expiration of a certain amount of time following application.
  • the amount of composition transferred to the substrate e.g., collar, or paper
  • a composition may be transfer resistant if a majority of the product is left on the wearer, e.g., lips, neck, etc.
  • the amount transferred may be compared with that transferred by other compositions, such as commercially available compositions. In a preferred embodiment of the present invention, little or no composition is transferred to the substrate.
  • Long wear compositions refers to compositions where at least one property chosen from consistency, texture, and color remains the same as at the time of application, as viewed by the naked eye, after an extended period of time, such as, for example, 1 hour, 2 hours, and further such as 8 hours.
  • Long wear properties may be evaluated by any method known in the art for evaluating such properties. For example, long wear may be evaluated by a test involving the application of a composition to human skin (including lips) and evaluating the consistency, texture and color of the composition after an extended period of time.
  • the consistency, texture and color of a lip composition may be evaluated immediately following application and these characteristics may then be re-evaluated and compared after an individual has worn the lip composition for a certain amount of time. Further, these characteristics may be evaluated with respect to other compositions, such as commercially available compositions.
  • Waterproof refers to the ability to repel water and permanence with respect to water. Waterproof properties may be evaluated by any method known in the art for evaluating such properties. For example, a mascara composition may be applied to false eyelashes, which may then be placed in water for a certain amount of time, such as, for example, 20 minutes.
  • the false eyelashes may be removed from the water and passed over a material, such as, for example, a sheet of paper.
  • a material such as, for example, a sheet of paper.
  • the extent of residue left on the material may then be evaluated and compared with other compositions, such as, for example, commercially available compositions.
  • a composition may be applied to skin, and the skin may be submerged in water for a certain amount of time.
  • the amount of composition remaining on the skin after the pre-ascertained amount of time may then be evaluated and compared.
  • a composition may be waterproof if a majority of the product is left on the wearer, e.g., eyelashes, skin, etc.
  • liquid fatty phase is understood to mean a fatty phase, which is liquid at room temperature (25°C.) and atmospheric pressure (760 mmHg), and which comprises one or more fatty substances that are liquid at room temperature, also known as oils, which are compatible with one another.
  • the phrase "structured liquid fatty phase” is understood to mean that this structured phase does not run between the fingers and is at least thickened.
  • the liquid fatty phase is structured, it makes it possible to limit exudation of the fatty phase from solid compositions, and furthermore, to limit, after deposition on the skin or the lips, its migration into the wrinkles and fine lines, which is desired for compositions such as a lipstick or an eyeshadow.
  • Significant migration of the liquid fatty phase, laden with coloring materials leads to an unaesthetic effect around the lips or the eyes, which can accentuate the wrinkles and fine lines. This migration is often mentioned by women as being a major defect of conventional lipsticks and eyeshadows.
  • the term “migration” is understood to mean running of the composition deposited on the lips or skin beyond its initial outline.
  • "Gloss” is essentially related to the nature of the liquid fatty phase. Thus, it is possible to reduce the level of waxes and fillers in the composition in order to increase the gloss of a lipstick, but then the migration of the liquid fatty phase increases. In other words, the levels of waxes and/or of fillers necessary for preparation of a stick of suitable hardness have been a restricting factor on the gloss of the deposit.
  • "Tackiness” as used herein refers to measuring the maximum tensile force, F max , required while separating two surfaces. Depending on the application envisaged and the formulation being designed, the desirable value for F max may vary.
  • the substantially non-tacky compositions have a Fmax of less than about 4 Newton (N), less than about 1 N, less than about 0.5 N, less than about 0.3 N, less than about 0.2 N or less than 0.1 N.
  • N the F ma ⁇ of the composition by, for example, determining the maximum force of traction, measured with an extensiometer of the LLOYD model LR ⁇ K type, needed to detach two surfaces.
  • a and B which are solid, rigid, inert, and non-absorbing, are mounted on movable mounts, facing each other.
  • the surfaces may be movable either toward or away from each other, or one may move surface A independently from surface B or vice versa.
  • surface A Prior to insertion into the extensiometer, surface A is coated with the composition to be measured, which may be dissolved in a solvent such as aqueous, hydroalcoholic, hydrocarbon, silicone, and alcoholic solvents in a concentration of from about 10 to about 30%, preferably 20%, the surface A is coated in a thickness of from 1 to 10 mil, preferably 1 mil, and the surface is dried for 24 hours at room temperature, e.g., 22 to 25°C, at a relative humidity of about 50%.
  • a solvent such as aqueous, hydroalcoholic, hydrocarbon, silicone, and alcoholic solvents
  • composition of the present invention may be in any form. For example, it may be a paste, a solid, a gel, or a cream.
  • It may be an emulsion, such as an oil-in-water or water-in-oil emulsion, a multiple emulsion, such as an oil-in-water-in-oil emulsion or a water-in-oil-in-water emulsion, or a solid, rigid or supple gel, including anhydrous gels.
  • the composition can also be in a form chosen from a translucent anhydrous gel and a transparent anhydrous gel.
  • the composition of the invention may, for example, comprise an external or continuous fatty phase.
  • the composition may be anhydrous.
  • the composition of the invention may be transparent or clear, including for example, a composition without pigments.
  • the composition can also be a molded composition or cast as a stick or a dish.
  • the composition in one embodiment is a solid such as a molded stick or a poured stick.
  • the compositions of the present invention may also be in the form a lip composition such as a lipstick or a liquid lip color, a foundation or a mascara, which exhibit excellent and improved properties of transfer-resistance, flexibility, pliability, adherence and lack of tackiness.
  • the structuring of the liquid fatty phase can be controlled by the type of polyorganosiloxane-containing polymer (or structuring polymer) used and is such that a rigid structure in the form of a stick, of good mechanical resistance, can be obtained.
  • compositions when colored, allow for a supple, light, non-transfer, non-migrating and/or long-wearing applications on a keratinous surface.
  • Such compositions may contain one or more structuring polymers.
  • stability is tested by placing the composition in a controlled environment chamber for 8 weeks at 25°C. In this test, the physical condition of the sample is inspected as it is placed in the chamber. The sample is then inspected again at 24 hours, 3 days, 1 week, 2 weeks, 4 weeks and 8 weeks.
  • the sample is examined for abnormalities in the composition such as phase separation if the composition is in the form of an emulsion, bending or leaning if the composition is in stick form, melting, or syneresis (or sweating).
  • the stability is further tested by repeating the 8-week test at 40°C, 37°C, 45°C, 50°C and under freeze-thaw conditions.
  • a composition is considered to lack stability if in any of these tests an abnormality that impedes functioning of the composition is observed.
  • the skilled artisan will readily recognize an abnormality that impedes functioning of a composition based on the intended application.
  • compositions comprising at least one polyorganosiloxane containing polymer chosen from homopolymers and copolymers, preferably, with a weight-average molecular mass ranging from about 500 to about 2.5 x 10 6 or more, comprising at least one moiety comprising: at least one polyorganosiloxane group comprising, preferably, from 1 to about 10,000 organosiloxane units in the chain of the moiety or in the form of a graft, and at least two groups capable of establishing hydrogen interactions are provided.
  • the polyorganosiloxane-containing polymers used in the composition of the invention may belong to the following two families: a) polyorganosiloxanes comprising at least two groups capable of establishing hydrogen interactions, these two groups being located in the polymer chain; and/or b) polyorganosiloxanes comprising at least two groups capable of establishing hydrogen interactions, these two groups being located on grafts or branches.
  • the polyorganosiloxane containing polymers of the present invention can be liquid or solid at room temperature. Preferably, the polymers are solid.
  • the polymers When the polymers are solid, it is preferable that they can be dissolved before or during use in a solvent with hydrogen interaction capable of breaking the hydrogen interactions of the polymers, for instance C 2 to Cs lower alcohols and especially ethanol, n-propanol or isopropanol. It is also possible to use these hydrogen interaction "breaking" solvents as co- solvents in the compositions of the present invention. These solvents may then be stored in the composition or may be removed by selective evaporation, which is well known to those skilled in the art. [041]
  • the polymers comprising two groups capable of establishing hydrogen interactions in the polymer chain may be polymers comprising at least one moiety corresponding to the formula:
  • R 1 , R 2 , R 3 and R 4 which may be identical or different, represent a group chosen from: linear, branched or cyclic, saturated or unsaturated, Ci to C 40 hydrocarbon-based groups, possibly containing in their chain one or more oxygen, sulphur and/or nitrogen atoms, and possibly being partially or totally substituted with fluorine atoms, C ⁇ to C-io aryl groups, optionally substituted with one or more Ci to C 4 alkyl groups, polyorganosiloxane chains possibly containing one or more oxygen, sulphur and/or nitrogen atoms; 2) the groups X, which may be identical or different, represent a linear or branched Ci to C 3 o alkylenediyl group, possibly containing in its chain one or more oxygen and/or nitrogen atoms; 3) Y is a saturated or unsaturated, Ci to C 50 linear or branched divalent alkylene, arylene, cycloalkylene, al
  • T represents a linear or branched, saturated or unsaturated, C 3 to C 24 trivalent or tetravalent hydrocarbon-based group optionally substituted with a polyorganosiloxane chain, and possibly containing one or more atoms chosen from O, N and S, or T represents a trivalent atom chosen from N, P and Al
  • R 5 represents a linear or branched Ci to C 50 alkyl group or a polyorganosiloxane chain, possibly comprising one or more ester, amide, urethane, thiocarbamate, urea, thiourea and/or sulphonamide groups, which may be linked to another chain of the polymer;
  • the groups G which may be identical or different, represent divalent groups chosen from:
  • R 6 represents a hydrogen atom or a linear or branched C ⁇ to C 2 o alkyl group, on condition that at least 50% of the groups R 6 of the polymer represents a hydrogen atom and that at least two of the groups G of the polymer are a group other than: O and .o. o o
  • n is an integer of at least 1 , for example ranging from 2 to 500 and preferably from 2 to 200
  • m is an integer of at least one, ranging from 1 to 35,000, for example, from 1 to 10,000 and 1 to 2,500, from 1 to 700 and from 6 to 200, including all values and subranges there between.
  • 80% of the groups R 1 , R 2 , R 3 and R 4 of the polymer are preferably chosen from methyl, ethyl, phenyl and 3,3,3-trifluoropropyl groups.
  • Y can represent various divalent groups, furthermore optionally comprising one or two free valencies to establish bonds with other moieties of the polymer or copolymer.
  • Y represents a group chosen from: a) linear Ci to C 2 o and preferably Ci to C-io alkylene groups, b) C 30 to C 56 branched alkylene groups possibly comprising rings and unconjugated unsaturations, c) C 5 -C 6 cycloalkylene groups, d) phenylene groups optionally substituted with one or more Ci to C 4 0 alkyl groups, e) Ci to C 2 o alkylene groups comprising from 1 to 5 amide groups, f) C 1 to C 2 o alkylene groups comprising one or more substituents chosen from hydroxyl, C 3 to C 8 cycloalkane, Ci to C 3 hydroxyalkyl and C-i to C 6 alkylamine groups, g) polyorganosiloxane
  • the polyorganosiloxanes of the second family may be polymers comprising at least one moiety corresponding to formula (II):
  • R 1 and R 3 which may be identical or different, are as defined above for formula (I)
  • R 7 represents a group as defined above for R 1 and R 3 , or represents a group of formula -X-G-R 9 in which X and G are as defined above for formula (I) and R 9 represents a hydrogen atom or a linear, branched or cyclic, saturated or unsaturated, Ci to C 50 hydrocarbon-based group optionally comprising in its chain one or more atoms chosen from O, S and N, optionally substituted with one or more fluorine atoms and/or one or more hydroxyl groups, or a phenyl group optionally substituted with one or more Ci to C 4 alkyl groups
  • R 8 represents a group of formula -X-G-R 9 in which X, G and R 9 are as defined above, - mi is an integer of at least one ranging from 1 to 35,000, for example, from 1 to10,000 and 1 to 2,500, from 1 to 700, and from 6 to 200, including all values
  • the polyorganosiloxane containing polymer may be a homopolymer, that is to say a polymer comprising several identical moieties, in particular moieties of formula (I) or of formula (II).
  • a polymer consisting of a copolymer comprising several different moieties of formula (I) that is to say a polymer in which at least one of the groups R 1 , R 2 , R 3 , R 4 , X, G, Y, m and n is different in one of the moieties.
  • the copolymer may also be formed from several moieties of formula (II), in which at least one of the groups R 1 , R 3 , R 7 , R 8 , mi and m 2 is different in at least one of the moieties.
  • a copolymer comprising at least one moiety of formula (I) and at least one moiety of formula (II), the moieties of formula (I) and the moieties of formula (II) possibly being identical to or different from each other.
  • a copolymer comprising at least one hydrocarbon-based moiety comprising two groups capable of establishing hydrogen interactions, chosen from ester, amide, sulphonamide, carbamate, thiocarbamate, urea and thiourea groups, and combinations thereof.
  • These copolymers may be block copolymers or grafted copolymers.
  • the groups capable of establishing hydrogen interactions are amide groups of formulae -C(O)NH- and -HN-C(O)-.
  • the polymer may comprise at least one moiety of formula (III) or (IV):
  • m is an integer of at least one as defined above, and preferably in the range from 1 to 700, for example, from 15 to 500 and from 15 to 45, including all values and subranges there between; and n is in particular in the range from 1 to 500, for example, from 1 to 100 and from 4 to 25, including all values and subranges there between;
  • X is preferably a linear or branched alkylene chain containing from 1 to 30 carbon atoms and in particular 3 to 10 carbon atoms, and Y is preferably an alkylene chain that is linear or branched or that possibly comprises rings and/or unsaturations, containing from 1 to 40 carbon atoms, including from 1 to 20 carbon atoms and from 2 to 6 carbon atoms, including all values and subranges there between, for example, 6 carbon atoms.
  • the alkylene group representing X or Y can optionally contain in its alkylene portion at least one of the following elements: 1) 1 to 5 amide, urea or carbamate groups, 2) a C 5 or C 6 cycloalkyl group, and 3) a phenylene group optionally substituted with 1 to 3 identical or different Ci to C 3 alkyl groups.
  • the alkylene groups may also be substituted with at least one element chosen from the group consisting of: a hydroxyl group, a C 3 to C 8 cycloalkyl group, one to three Ci to C 4 o alkyl groups, a phenyl group optionally substituted with one to three Ci to C 3 alkyl groups, a Ci to C 3 hydroxyalkyl group, and a Ci to C 6 aminoalkyl group.
  • Y may also represent:
  • R 5 represents a polyorganosiloxane chain and T represents a group of formula: -(CH,) a _ -(CH 2 ) b . or - (CH 2 ) a _N . (CH 2 ) b .
  • R 1 , R 2 , R 3 and R 4 preferably represent, independently, a linear or branched C 1 to C 40 alkyl group, preferably a CH 3 , C 2 H 5 , n-C 3 H 7 or isopropyl group, a polyorganosiloxane chain or a phenyl group optionally substituted with one to three methyl or ethyl groups.
  • the polymer may comprise identical or different moieties of formula (III) or (IV).
  • the polymer may be a polyamide containing several moieties of formula (III) or (IV) of different lengths, i.e. a polyamide corresponding to the formula:
  • the moieties may be structured to form either a block copolymer, or a random copolymer or an alternating copolymer. In this copolymer, the moieties may be not only of different lengths, but also of different chemical structures, for example containing different groups Y. In this case, the copolymer may correspond to the formula:
  • the various moieties may be structured to form either a block copolymer, or a random copolymer or an alternating copolymer.
  • the polyorganosiloxane- containing polymer may also contain a grafted copolymer.
  • the polyamide containing silicone units may be grafted and optionally crosslinked with silicone chains containing amide groups.
  • Such polymers may be synthesized with trifunctional amines.
  • the copolymer may comprise at least one moiety of formula:
  • R 19 is a hydrogen atom or a group chosen from the groups defined for R 1 to R 4
  • R 20 , R 21 and R 22 are, independently, linear or branched alkylene groups, and more preferably corresponds to the formula: R -N -R 2 ⁇
  • R 20 , R 21 and R 22 representing -CH 2 -CH 2 -, mi and m 2 are in the range from 15 to 500, including from 15 to 45 and including all values and subranges there between, X 1 and X 2 represent -(CH 2 ) ⁇ 0 -, and Y represents -CH -.
  • These polyamides containing a grafted silicone moiety of formula (VII) may be copolymerized with polyamide-silicones of formula (II) to form block copolymers, alternating copolymers or random copolymers.
  • the weight percentage of grafted silicone moieties (VII) in the copolymer may range from 0.5% to 30% by weight.
  • the siloxane units may be in the main chain or backbone of the polymer, but they may also be present in grafted or pendent chains.
  • the siloxane units may be in the form of segments as described above.
  • the siloxane units may appear individually or in segments.
  • the preferred siloxane-based polyamides are: polyamides of formula (III) in which m is from 15 to 300, for example, 15 to 100, including all values and subranges there between; mixtures of two or more polyamides in which at least one polyamide has a value of m in the range from 15 to 50, including all values and subranges there between and at least one polyamide has a value of m in the range from 30 to 300, including all values and subranges there between; polymers of formula (V) with mi chosen in the range from 15 to 50 and m 2 chosen in the range from 30 to 500 with the portion corresponding to mi representing 1 % to 99% by weight of the total weight of the polyamide and the corresponding portion m 2 representing 1% to 99% by weight of the total weight of the polyamide; mixtures of polyamide of formula (III) combining 1 ) 80% to 99% by weight of a polyamide in which n is equal to 2 to 10 and in particular 3 to 6, and 2) 1 % to
  • the end groups of the polymer chain may end with: a Ci to C5 0 alkyl ester group by introducing a Ci to C 50 monoalcohol during the synthesis, a Ci to C 50 alkylamide group by taking as stopping group a monoacid if the silicone is ⁇ , ⁇ -diaminated, or a monoamine if the silicone is an ⁇ , ⁇ - dicarboxylic acid.
  • a copolymer of silicone polyamide and of hydrocarbon-based polyamide i.e. a copolymer comprising moieties of formula (III) or (IV) and hydrocarbon-based polyamide moieties.
  • polyamide-silicone moieties may be arranged at the ends of the hydrocarbon-based polyamide.
  • Polyamide-based polymers containing silicones may be produced by silylic amidation of polyamides based on fatty acid dimer. This approach involves the reaction of free acid sites existing on a polyamide as end sites, with organosiloxane-monoamines and/or organosiloxane- diamines (amidation reaction), or alternatively with oligosiloxane alcohols or oligosiloxane diols (esterification reaction). The esterification reaction requires the presence of acid catalysts, as is known in the art.
  • the polyamide containing free acid sites, used for the amidation or esterification reaction it is desirable for the polyamide containing free acid sites, used for the amidation or esterification reaction, to have a relatively high number of acid end groups (for example polyamides with high acid numbers, for example from 15 to 20).
  • siloxane diamines with 1 to 300, more particularly 2 to 50 and for example, 2, 6, 9.5, 12, 13.5, 23 or 31 siloxane groups, may be used for the reaction with hydrocarbon-based polyamides based on fatty acid dimers.
  • Siloxane diamines containing 13.5 siloxane groups are preferred, and the best results are obtained with the siloxane diamine containing 13.5 siloxane groups and polyamides containing high numbers of carboxylic acid end groups.
  • the reactions may be carried out in xylene to extract the water produced from the solution by azeotropic distillation, or at higher temperatures (about 180 to 200°C) without solvent. Typically, the efficacy of the amidation and the reaction rates decrease when the siloxane diamine is longer, that is to say when the number of siloxane groups is higher.
  • Free amine sites may be blocked after the initial amidation reaction of the diaminosiloxanes by reacting them either with a siloxane acid, or with an organic acid such as benzoic acid.
  • this may be performed in boiling xylene with about 1 % by weight, relative to the total weight of the reagents, of para-toluenesulphonic acid as catalyst.
  • These reactions carried out on the carboxylic acid end groups of the polyamide lead to the incorporation of silicone moieties only at the ends of the polymer chain.
  • the copolymer of hydrocarbon-based polyamide and of polyamide-silicone may also be a grafted copolymer comprising a hydrocarbon-based polyamide backbone with pendent oligosiloxane groups.
  • This may be obtained, for example: by hydrosilylation of unsaturated bonds in polyamides based on fatty acid dimers; by silylation of the amide groups of a polyamide; or by silylation of unsaturated polyamides by means of an oxidation, that is to say by oxidizing the unsaturated groups into alcohols or diols, to form hydroxyl groups that are reacted with siloxane carboxylic acids or siloxane alcohols.
  • the olefinic sites of the unsaturated polyamides may also be epoxidized and the epoxy groups may then be reacted with siloxane amines or siloxane alcohols.
  • the polyorganosiloxane containing polymers used in the composition of the invention are most preferably polymers of the polyorganosiloxane type such as those described in documents US 5,874,069, US 5,919,441 , US 6,051 ,216 and US 5,981 ,680, the entire disclosures of which are hereby incorporated by reference.
  • the polyorganoxiloxane containing polymer is a homopolymer or a copolymer comprising urethane or urea groups.
  • the polymer may comprise polyorganosiloxane moieties containing two or more urethane and/or urea groups, either in the backbone of the polymer or on side chains or as pendent groups.
  • the polymers comprising at least two urethane and/or urea groups in the backbone may be polymers comprising at least one moiety corresponding to the following formula:
  • O corresponds to a urethane or urea group.
  • Y may be a linear or branched Ci to C o alkylene group, optionally substituted with a Ci to C- 15 alkyl group or a C 5 to C- 10 aryl group.
  • a -(CH 2 )6- group is used.
  • Y may also represent a C 5 to C 12 cycloaliphatic or aromatic group that may be substituted with a Ci to C 15 alkyl group or a C 5 to C 10 aryl group, for example a radical chosen from the methylene-4,4-biscyclohexyl radical, the radical derived from isophorone diisocyanate, 2,4- and 2,6-tolylenes, 1 ,5-naphthylene, p-phenylene and 4,4'-biphenylenemethane.
  • Y it is preferred for Y to represent a linear or branched Ci to C 40 alkylene radical or a C to C 12 cycloalkylene radical.
  • Y may also represent a polyurethane or polyurea block corresponding to the condensation of several diisocyanate molecules with one or more molecules of coupling agents of the diol or diamine type.
  • Y comprises several urethane or urea groups in the alkylene chain.
  • B is a group chosen from the groups given above for Y, U is -O- or -NH- and B 2 is chosen from: linear or branched Ci to C 0 alkylene groups, which can optionally bear an ionizable group such as a carboxylic acid or sulphonic acid group, or a neutralizable or quatemizable tertiary amine group, C 5 to C 12 cycloalkylene groups, optionally bearing alkyl substituents, for example one to three methyl or ethyl groups, or alkylene, for example the diol radical: cyclohexanedimethanol, phenylene groups that may optionally bear Ci to C 3 alkyl substituents, and groups of formula:
  • T is a hydrocarbon-based trivalent radical possibly containing one or more hetero atoms such as oxygen, sulphur and nitrogen and R 5 is a polyorganosiloxane chain or a linear or branched Ci to C 50 alkyl chain.
  • R 5 is a polyorganosiloxane chain or a linear or branched Ci to C 50 alkyl chain.
  • Y is a linear or branched Ci to C 40 alkylene group
  • the -(CH 2 ) 2 - and -(CH 2 ) ⁇ - groups are preferred.
  • d may be an integer ranging from 0 to 5, preferably from 0 to 3 and more preferably equal to 1 or 2.
  • B 2 is a linear or branched Ci to C 40 alkylene group, in particular -(CH 2 )2- or -(CH 2 ) ⁇ - or a group:
  • the polyorganosiloxane containing polymer may be formed from silicone urethane and/or silicone urea moieties of different length and/or constitution, and may be in the form of block or random copolymers.
  • the silicone may also comprise urethane and/or urea groups no longer in the backbone but as side branches.
  • the polymer may comprise at least one moiety of formula:
  • R )1', R D2 , R D 3 ⁇ i and m 2 have the meanings given above for formula (I)
  • U represents O or NH
  • R 23 represents a Ci to C 40 alkylene group, optionally comprising one or more hetero atoms chosen from O and N, or a phenylene group
  • R 24 is chosen from linear, branched or cyclic, saturated or unsaturated Ci to C 50 alkyl groups, and phenyl groups optionally substituted with one to three Ci to C 3 alkyl groups.
  • the polymers comprising at least one moiety of formula (X) contain siloxane units and urea or urethane groups, and they may be used , for example, as gelling agents in the compositions of the invention.
  • the siloxane polymers may have a single urea or urethane group by branching or may have branches containing two urea or urethane groups, or alternatively they may contain a mixture of branches containing one urea or urethane group and branches containing two urea or urethane groups. [095] They may be obtained from branched polysiloxanes, comprising one or two amino groups by branching, by reacting these polysiloxanes with monoisocyanates. [096] As examples of starting polymers of this type containing amino and diamino branches, mention may be made of the polymers corresponding to the following formulae:
  • Such polymers containing branching may be formed by reacting a siloxane polymer, containing at least three amino groups per polymer molecule, with a compound containing only one monofunctional group (for example an acid, an isocyanate or an isothiocyanate) to react this monofunctional group with one of the amino groups and to form groups capable of establishing hydrogen interactions.
  • a siloxane polymer containing at least three amino groups per polymer molecule
  • a compound containing only one monofunctional group for example an acid, an isocyanate or an isothiocyanate
  • the amino groups may be on side chains extending from the main chain of the siloxane polymer, such that the groups capable of establishing hydrogen interactions are formed on these side chains, or alternatively the amino groups may be at the ends of the main chain, such that the groups capable of hydrogen interaction will be end groups of the polymer.
  • a procedure for forming a polymer containing siloxane units and groups capable of establishing hydrogen interactions mention may be made of the reaction of a siloxane diamine and of a diisocyanate in a silicone solvent so as to provide a gel directly. The reaction may be performed in a silicone fluid, the resulting product being dissolved in the silicone fluid, at high temperature, the temperature of the system then being reduced to form the gel.
  • the polymers that are preferred for incorporation into the compositions according to the present invention are siloxane-urea copolymers that are linear and that contain urea groups as groups capable of establishing hydrogen interactions in the backbone of the polymer.
  • siloxane-urea copolymers that are linear and that contain urea groups as groups capable of establishing hydrogen interactions in the backbone of the polymer.
  • the polymers of formula (VIII) comprising urea or urethane groups in the chain of the silicone polymer may be obtained by reaction between a silicone containing ⁇ , ⁇ -NH 2 or -OH end groups, of formula:
  • Y may have the formula (IX) with d equal to 0 or d equal to 1 to 5.
  • the copolymer may correspond, for example, to the formula:
  • Branched polyurethane or polyurea silicones may also be obtained using, instead of the diisocyanate OCN-Y-NCO, a triisocyanate of formula:
  • a polyurethane or polyurea silicone containing branches comprising an organosiloxane chain with groups capable of establishing hydrogen interactions is thus obtained.
  • Such a polymer comprises, for example, a moiety corresponding to the formula:
  • this copolymer can also comprise polyurethane silicone moieties without branching.
  • the siloxane-based polyureas and polyurethanes that are preferred are: polymers of formula (VIII) in which m is from 15 to 300, for example, 15 to 100 and all values and subranges there between; mixtures of two or more polymers in which at least one polymer has a value of m in the range from 15 to 50 and at least one polymer has a value of m in the range from 30 to 300, including all values and subranges there between; polymers of formula (XII) with mi chosen in the range from 15 to 50 and m 2 chosen in the range from 30 to 500 with the portion corresponding to mi representing 1 % to 99% by weight of the total weight of the polymer and the portion corresponding to m 2 representing 1 % to 99% by weight of the total weight of the polymer; mixtures of polymer of formula (VIII) combining 1 ) 80% to 99% by weight of a polymer in which n is equal to 2 to 10 and in particular 3 to 6, and 2)
  • copolymers of polyurethane or polyurea silicone and of hydrocarbon-based polyurethane or polyurea may be used in the invention by performing the reaction for synthesizing the polymer in the presence of an ⁇ , ⁇ -difunctional block of non-silicone nature, for example a polyester, a polyether or a polyolefin.
  • homopolymers or copolymers of the invention may contain siloxane moieties in the main chain of the polymer and groups capable of establishing hydrogen interactions, either in the main chain of the polymer or at the ends thereof, or on side chains or branches of the main chain. This may correspond to the following five arrangements: I L_J I. i — I I I ⁇ I - ⁇ (2)
  • the continuous line is the main chain of the siloxane polymer and the squares represent the groups capable of establishing hydrogen interactions.
  • the groups capable of establishing hydrogen interactions are arranged at the ends of the main chain.
  • two groups capable of establishing hydrogen interactions are arranged at each of the ends of the main chain.
  • the groups capable of establishing hydrogen interactions are arranged within the main chain in repeating moieties.
  • these are copolymers in which the groups capable of establishing hydrogen interactions are arranged on branches of the main chain of a first series of moieties that are copolymerized with moieties not comprising groups capable of establishing hydrogen interactions.
  • the values n, x and y are such that the polymer has the desired properties in terms of an agent for gelling fatty phases, preferably fatty phases based on non-silicone oil.
  • an agent for gelling fatty phases preferably fatty phases based on non-silicone oil.
  • Further examples of polyorganosiloxane containing polymers are set forth in U.S. patents 6,503,632 and 6,569,955, both of which are hereby incorporated by reference in their entirety.
  • the polymers of the present invention can be solid or liquid at room temperature.
  • the polymers When solid, the polymers preferably have a softening point from 50 to 130°C. Most preferably, they have a softening point ranging from 65 to 150°C, including from 70°C to 130°C. This softening point is lower than that of other structuring polymers, which facilitates the use of the polymers that are the subject of the invention, and limits the deteriorations of the liquid fatty phase.
  • the polyorganosiloxane containing polymers of the present invention contain both siloxane units and at least two groups capable of establishing hydrogen interactions such as amide linkages.
  • the siloxane units can provide compatibility with a silicone fluid, if present, (for example with the cyclomethicones), while the groups capable of establishing hydrogen interactions and the spacing and selection of the locations of the amide linkages can facilitate gelation and the formation of cosmetic products.
  • the polyorganosiloxane containing polymer of the present invention is present in an amount effective to provide transfer resistant properties, and may also provide at least one of the following properties: pliability, softness, and wearing comfort.
  • the compositions of the invention exhibit flexibility and/or good adherence on the keratinous substance to which the compositions have been applied.
  • the compositions of the present invention when applied to the keratinous substance are substantially non-tacky.
  • the polyorganosiloxane-containing polymers are preferably present in an amount of 0.1-80 percent by weight, more preferably from 0.5 to 30 percent by weight and most preferably from 1 to 20 percent by weight of the total weight of the composition.
  • hardness of the composition may also be considered.
  • the hardness of a composition may, for example, be expressed in gramforce (gf).
  • the composition of the present invention may, for example, have a hardness ranging from 20 gf to 2000 gf, such as from 20 gf to 900 gf, and further such as from 20 gf to 600 gf .
  • This hardness is measured in one of two ways.
  • a first test for hardness is according to a method of penetrating a probe into the composition and in particular using a texture analyzer (for example TA-XT2i from Rheo) equipped with an ebonite cylinder of height 25 mm and diameter 8 mm.
  • the hardness measurement is carried out at 20°C at the center of 5 samples of the composition.
  • the cylinder is introduced into each sample of composition at a pre-speed of 2 mm/s and then at a speed of 0.5 mm/s and finally at a post-speed of 2 mm/s, the total displacement being 1 mm.
  • the recorded hardness value is that of the maximum peak observed.
  • the measurement error is ⁇ 50gf.
  • the second test for hardness is the "cheese wire” method, which involves cutting an 8.1 mm or preferably 12.7 mm in diameter stick composition and measuring its hardness at 20°C using a DFGHS 2 tensile testing machine from Indelco-Chatillon Co. at a speed of 100 mm/minute.
  • the hardness value from this method is expressed in grams as the shear force required to cut a stick under the above conditions.
  • the hardness of compositions according to the present invention which may be in stick form may, for example, range from 30 gf to 300 gf, such as from 30 gf to 250 gf, for a sample of 8.1 mm in diameter stick, and further such as from 30 gf to 200 gf, and also further such as from 30 gf to 120 gf for a sample of 12.7 mm in diameter stick.
  • the hardness of the composition of the present invention may be such that the compositions are self-supporting and can easily disintegrate to form a satisfactory deposit on a keratinous material.
  • this hardness may impart good impact strength to the inventive compositions, which may be molded or cast, for example, in stick or dish form.
  • the skilled artisan may choose to evaluate a composition using at least one of the tests for hardness outlined above based on the application envisaged and the hardness desired. If one obtains an acceptable hardness value, in view of the intended application, from at least one of these hardness tests, the composition falls within preferred embodiments of the invention.
  • the hardness of the composition according to preferred embodiments of the invention may, for example, be such that the composition is advantageously self-supporting and can disintegrate easily to form a satisfactory deposit on the skin and/or the lips and/or superficial body growths, such as keratinous fibers.
  • the composition of the invention may have good impact strength.
  • the composition in stick form may have the behavior of a deformable, flexible elastic solid, giving noteworthy elastic softness on application.
  • the compositions in stick form of the prior art do not have these properties of elasticity and flexibility.
  • LIQUID FATTY PHASE [0130]
  • cosmetic compositions comprising at least one polyorganosiloxane containing polymer and a liquid fatty phase are provided.
  • the liquid fatty phase is substantially free of silicone oils, preferably devoid of silicone oil, and comprises at least one volatile non-silicone oil, e.g., a hydrocarbon volatile oil, or mixtures of hydrocarbon volatile oils.
  • the liquid fatty phase may contain, independently or in combinations, volatile non-silicone oils, non- volatile non-silicone oils, or mixtures of these.
  • substantially free of silicone oils as used herein means that the composition contains less than about 0.5 % silicone oils
  • devoid of silicone oils as used herein means that the composition contains less than about 0.1 % silicone oils.
  • the compositions of the present invention are "free of silicone oils,” meaning no detectable quantities of silicone oil in the composition, it being understood to one of skill in the art that some undetectable quantity of silicone oil may be present.
  • the non-silicone volatile oils when volatile non-silicone oils are present, these volatile oils permit an easier application of the composition on the skin, lips or keratinous fibers.
  • the volatility of the solvents/oils can be determined using the evaporation speed as set forth in U.S. patent no. 6,338,839.
  • the non-silicone volatile oils may be selected from volatile hydrocarbon oils, alcohols, volatile esters and volatile ethers.
  • volatile non-silicone oils include, but are not limited to, volatile hydrocarbon oils having from 8 to 16 carbon atoms and their mixtures and in particular branched Cs to C 16 alkanes such as C ⁇ to Ci ⁇ isoalkanes (also known as isoparaffins), isododecane, isodecane, isohexadecane, and for example, the oils sold under the trade names of Isopar or Permethyl, the C 8 to C-i ⁇ branched esters such as isohexyl or isodecyl neopentanoate and their mixtures.
  • the volatile non- silicone oils have a flash point of at least 40°C.
  • polar oils
  • alkyl benzoate isopropyl myristate, 2-ethylhexyl palmitate, and octanoates, decanoates or ricinoleates of alcohols or of polyalcohols; hydroxylated esters, for instance isostearyl lactate or diisostearyl malate; and pentaerythritol esters; - synthetic ethers containing from 10 to 40 carbon atoms; - Cs to C 26 fatty alcohols, for instance oleyl alcohol; and - mixtures thereof.
  • the liquid fatty phase when present, represents from 5% to 98.4% of the total weight of the composition, more preferably from 10% to 80% of the total weight of the composition, and most preferably from 20% to 75%.
  • Film Formers are known in the art.
  • compositions comprising at least one polyorganosiloxane containing polymer and at least one silicone film forming agent, preferably an MK or MQ resin or mixtures thereof, are provided.
  • Silicone resin nomenclature is known in the art as "MDTQ” nomenclature, whereby a silicone resin is described according to the various monomeric siloxane units which make up the polymer.
  • MDTQ silicone resin
  • M denotes the monofunctional unit (CH 3 ) 3 SiO ⁇ /2 . This unit is considered to be monofunctional because the silicone atom only shares one oxygen when the unit is part of a polymer.
  • the "M” unit can be represented by the following structure:
  • At least one of the methyl groups of the M unit may be replaced by another group, e.g., to give a unit with formula [R(CH 3 ) 2 ]SiO ⁇ /2 , as represented in the following structure:
  • R is chosen from groups other than methyl groups.
  • groups other than methyl groups include alkyl groups other than methyl groups, alkene groups, alkyne groups, hydroxyl groups, thiol groups, ester groups, acid groups, ether groups, wherein the groups other than methyl groups may be further substituted.
  • the symbol D denotes the difunctional unit (CH 3 ) 2 SiO 2 /2 wherein two oxygen atoms bonded to the silicone atom are used for binding to the rest of the polymer.
  • the "D" unit which is the major building block of dimethicone oils, can be represented as:
  • At least one of the methyl groups of the D unit may be replaced by another group, e.g., to give a unit with formula [R(CH 3 ) 2 ]SiO ⁇ /2 .
  • T denotes the trifunctional unit, (CH 3 )SiO 32 and can be represented as:
  • At least one of the methyl groups of the T unit may be replaced by another group, e.g., to give a unit with formula [R(CH 3 ) 2 ]SiO-i /2 .
  • the symbol Q denotes the tetrafunctional unit, SiO /2 wherein all four oxygens bonded to the silicone atom are bonded to the rest of the polymer.
  • silicone polymers include silanes, siloxanes, siloxysilicates, and silsesquioxanes.
  • PDMS polydimethylsiloxane
  • Polydimethylsiloxanes are generally composed of long straight chains of (CH 3 ) 2 SiO 22 (i.e., D units) and have viscosities which are dependent on both the size of the polymer and the presence and nature of any substituent(s) on the polymer.
  • a non-limiting example of a siloxysilicate is trimethylsiloxysilicate, which may be represented by the following formula: [0154] [(CH 3 )3-Si-O] ⁇ -(SiO 4 /2)y [0155] (i.e, MQ units) wherein x and y may, for example, range from 50 to 80.
  • Silsesquioxanes may be represented by the following formula: [0157] (i.e., T Units) wherein x may, for example, have a value of up to several thousand.
  • x may, for example, have a value of up to several thousand.
  • Polymethylsilsesquioxanes are silsesquioxanes that do not have a substituent replacing the methyl groups. Certain polymethylsilsesquioxanes have previously been used in hair care compositions. See, e.g., U.S. Pat. No.
  • a shampoo composition comprising a surfactant, an aqueous emulsion of highly viscous silicone in volatile silicone and a cationic polymer which is a derivative of guar gum.
  • the highly viscous silicone disclosed therein may be chosen from silicone resins including a polymethylsilsesquioxane such as Resin MK (also called SiliconHarz MK) which is available from Wacker, and a siloxysilicate such as Resin MQ which is available from General Electric and Dow Corning.
  • Resin MK and Resin MQ silicone resins may form a film after a volatile carrier has evaporated.
  • the silicone film former may be a polymethylsilsesquioxane film former such as Belsil PMS MK, also referred to as Resin MK, available from Wacker Chemie.
  • This polymethylsilsesquioxane film former is a polymer comprising polymerized repeating units of CH 3 SiO 3/2 (T units) and may also contain up to 1% by weight or by mole of units of the formula (CH 3 )2SiO22 (D units).
  • the weight- average molecular weight of this polymer has been estimated to be 10,000. It is believed that the polymers are in a "cage" and “ladder” configuration, as exemplified in the figures below. The majority of the polymer is in the "ladder” configuration, wherein the ends of the polymer are capped with ethoxy (CH 3 CH 2 O) groups. The ethoxy groups are generally present in an amount of 4.5% by weight and the mole percent is generally 7% (silicone units). As ethoxy groups may react with water, a small and variable amount of SiOH may also be present in the polymer.
  • KR-220L Another non-limiting example of the at least one polymethylsilsesquioxane film former suitable for use in the present invention is KR-220L, which is available from SHIN-ETSU.
  • This polymethylsilsesquioxane film former is composed of silicone T-units (i.e., those of formula CH 3 SiO 3/2 ) and has Si-OH (or silanol) end units. There are no D units in KR-220L.
  • At least one polymethylsilsesquioxane film former that may be useful in the practice of the invention include KR-242A (which is comprised of methyl T units (98%) and dimethyl D units (2%) and has Si-OH end units) and KR-251 (which is comprised of methyl T units (88%) and dimethyl D units (12%) and has Si- OH end units), both of which are available from SHIN-ETSU.
  • KR-242A which is comprised of methyl T units (98%) and dimethyl D units (2%) and has Si-OH end units
  • KR-251 which is comprised of methyl T units (88%) and dimethyl D units (12%) and has Si- OH end units
  • concentration of the at least one polymethylsilsesquioxane film former in the presently claimed composition may vary considerably.
  • the silicone film former may be chosen from siloxysilicates.
  • the siloxysilicate is trimethylsiloxysilicate, which may or may not be in powder form.
  • Trimethylsiloxysilicate (TMS) is commercially available from General Electric under the tradename SR1000 and from Wacker under the tradename TMS 803.
  • TMS is also commercially available from Dow Chemical in a solvent, such as for example, cyclomethicone.
  • TMS may be used in the form of 100% active material, that is, not in a solvent.
  • silicone film formers include silicone/(meth)acrylate copolymers, such as those as described in US Patent Nos. 5,061 ,481 , 5,219,560, and 5,262,087, the disclosures of which are hereby incorporated by reference. Still further non-limiting examples of silicone film formers are non-polar silicone copolymers comprising repeating units of at least one polar (meth)acrylate unit and vinyl copolymers grafted with at least one non-polar silicone chain.
  • Non-limiting examples of such copolymers are acrylates/dimethicone copolymers such as those commercially available from Shin-Etsu, for example, the product sold under the tradename KP-545, or acrylates/stearyl acrylate/dimethicone acrylates copolymers, such as those commercially available from Shin-Etsu, for example, the product sold under the tradename KP-561 , and acrylates/behenyl acrylate/dimethicone acrylates copolymer, such as those commercially available from Shin-Etsu, for example, the product sold under the tradename KP-562.
  • silicone film formers suitable for use in the present invention are silicone esters comprising units of formulae (XIV) and (XV), disclosed in U.S. Pat. Nos. 6,045,782, 5,334,737, and 4,725,658, the disclosures of which are hereby incorporated by reference: R a R E b SiO [4-(a+ b)/2] (XIV); and wherein R and R', which may be identical or different, are each chosen from optionally substituted hydrocarbon groups; a and b, which may be identical or different, are each a number ranging from 0 to 3, with the proviso that the sum of a and b is a number ranging from 1 to 3, x and y, which may be identical or different, are each a number ranging from 0 to 3, with the proviso that the sum of x and y is a number ranging from 1 to 3; R E , which may be identical or different, are each chosen from groups comprising at least one carboxylic
  • R E groups are chosen from groups comprising at least one ester group formed from the reaction of at least one acid and at least one alcohol.
  • the at least one acid comprises at least two carbon atoms.
  • the at least one alcohol comprises at least ten carbon atoms.
  • Non-limiting examples of the at least one acid include branched acids such as isostearic acid, and linear acids such as behenic acid.
  • Non-limiting examples of the at least one alcohol include monohydric alcohols and polyhydric alcohols, such as n- propanol and branched etheralkanols such as (3,3,3- trimethylolpropoxy)propane.
  • the at least one silicone film former include liquid siloxy silicates and silicone esters such as those disclosed in U.S. Pat. No. 5,334,737, the disclosure of which is hereby incorporated by reference, such as diisostearoyl trimethylolpropane siloxysilicate and dilauroyl trimethylolpropane siloxy silicate, which are commercially available from General Electric under the tradenames SF 1318 and SF 1312, respectively.
  • Yet further non-limiting examples of the at least one silicone film former include polymers comprising a backbone chosen from vinyl polymers, methacrylic polymers, and acrylic polymers and at least one chain chosen from pendant siloxane groups and pendant fluorochemical groups.
  • Non-limiting examples of such polymers comprise at least one unit derived from at least one A monomer, at least one unit derived from at least one C monomer, at least one unit derived from D monomers, and, optionally, at least one unit derived from at least one B monomer, wherein: [0170] A, which may be identical or different, are each chosen from free-radically-polymerizable acrylic esters of at least one alcohol chosen from 1 ,1 ,-dihydroperfluoroalkanols, omega-hydridofluoroalkanols, fluoroalkylsulfonamido alcohols, cyclic fluoroalkyl alcohols, and fluoroether alcohols, and analogs of any of the foregoing at least one alcohols, and free- radically-polymerizable methacrylic esters of at least one alcohol chosen from 1 ,1 ,-dihydroperfluoroalkanols, omega-hydridofluoroalkanols,
  • At least one silicone film former include silicone/acrylate graft terpolymers, for example, those having the formula:
  • R and R-i which may be identical or different, are each chosen from hydrogen and C ⁇ -C 6 alkyl groups; and] m is a number ranging from 100 - 150.
  • m is chosen to provide a macromer having a molecular weight ranging from 8,000 to 12,000, such as 10,000.
  • m is a number ranging from 124-135, such as 130.
  • Non-limiting examples of these copolymers are described in WO 01/32727 A1 , the disclosure of which is hereby incorporated by reference.
  • silicone film formers include copolymers comprising a backbone chosen from vinyl backbones, methacrylic backbones, and acrylic polymeric backbones and further comprising at least one pendant siloxane group.
  • a backbone chosen from vinyl backbones, methacrylic backbones, and acrylic polymeric backbones and further comprising at least one pendant siloxane group.
  • Non-limiting examples of such polymers are disclosed in U.S. Pat. Nos. 4,693,935, 4,981,903, 4,981 ,902, the disclosures of which are hereby incorporated by reference.
  • the at least one copolymer comprises at least one A monomer, at least one C monomer, and, optionally at least one B monomer, wherein the at least one A monomer is chosen from free- radically-polymerizable vinyl monomers, free-radically-polymerizable methacrylate monomers, and free-radically-polymerizable acrylate monomers; the at least one B monomer, if present, is chosen from at least one reinforcing monomer copolymerizable with the at least one A monomer, and the at least one C monomer is chosen from monomers having the formula: X(Y) n Si(R) 3-m Z m wherein: X is chosen from vinyl groups which are copolymerizable with the at least one A monomer and with the at least one B monomer; Y is chosen from divalent groups; n is zero or 1 ; m is a number ranging from 1 to 3; R, which may be identical or different, are each chosen from hydrogen, optionally
  • Non-limiting examples of A monomers include methacrylic acid esters of C 1 ..C 12 linear alcohols, methacrylic acid esters of C ⁇ -C ⁇ 2 of branched alcohols, styrene monomers, vinyl esters, vinyl chloride monomers, vinylidene chloride monomers, and acryloyl monomers.
  • Non-limiting examples of B monomers include acrylic monomers comprising at least one group chosen from hydroxyl, amino, and ionic groups, and methacrylic monomers comprising at least one group chosen from hydroxyl, amino, and ionic groups.
  • Non-limiting examples of ionic groups include quaternary ammonium groups, carboxylate salts, and sulfonic acid salts.
  • silicone film-former examples include a copolymer chosen from vinyl-silicone graft copolymers having the following formula and vinyl-silicone block copolymers having the following formula: wherein G 5 , which may be identical or different, are each chosen from alkyl groups, aryl groups, aralkyl groups, alkoxy groups, alkylamino groups, fluoroalkyl groups, hydrogen, and -ZSA groups, wherein A is chosen from vinyl polymeric segments comprising at least one polymerized free-radically-polymerizable monomer, and Z is chosen from divalent Ci-Cio alkylene groups, divalent aralkylene groups, divalent arylene groups, and divalent alkoxylalkylene groups.
  • Z is chosen from methylene groups and propylene groups.
  • G 6 which may be identical or different, are each chosen from alkyl groups, aryl groups, aralkyl groups, alkoxy groups, alkylamino groups, fluoroalkyl groups, hydrogen, and -ZSA groups, as defined above;
  • G 2 comprises A;
  • G comprises A;
  • R-i which may be identical or different, are each chosen from alkyl groups, aryl groups, aralkyl groups, alkoxy groups, alkylamino groups, fluoroalkyl groups, hydrogen, and hydroxyl.
  • Ri is chosen from C ⁇ _C alkyl groups, such as methyl groups, and hydroxyl.
  • R 2 which may be identical or different, are each chosen from divalent C ⁇ - ⁇ o alkylene groups, divalent arylene groups, divalent aralkylene groups, and divalent alkoxyalkylene groups.
  • R 2 is chosen from divalent C-i- C 3 alkylene groups and divalent C 7- C ⁇ o aralkylene groups.
  • R 2 is chosen from -CH 2 - groups and divalent 1 ,3-propylene groups.
  • R 3 which may be identical or different, are each chosen from alkyl groups, aryl groups, aralkyl groups alkoxy groups, alkylamino groups, fluoroalkyl groups, hydrogen, and hydroxyl.
  • R 3 is chosen from C ⁇ _C 4 alkyl groups and hydroxyl. In another embodiment, R 3 is chosen from methyl groups.
  • R which may be identical or different, are each chosen from divalent C 1 -C 10 alkylene groups, divalent arylene groups, divalent aralkylene groups, and divalent alkoxyalkylene groups.
  • R 4 is chosen from divalent C ⁇ _ C 3 alkylene groups and divalent C 7 -C- 10 aralkylene groups.
  • R is chosen from divalent -CH 2 - groups and divalent 1 ,3-propylene groups, x is a number ranging from 0 to 3; y is a number greater than or equal to 5.
  • y ranges from 10 to 270, and in another embodiment, y ranges from 40 to 270.
  • q is a number ranging from 0 to 3;
  • Non-limiting examples of these polymers are described in U.S. Pat. No. 5,468,477, the disclosure of which is hereby incorporated by reference.
  • a non-limiting example of such polymers is poly(dimethylsiloxane)-g-poly(isobutyl methacrylate), which is commercially available from 3M Company under the tradename VS 70 IBM.
  • the silicone film former is present in the composition in an amount ranging from 0.1% to 30% by weight relative to the total weight of the composition.
  • the silicone film former is present in an amount ranging from 0.5% to 20% by weight relative to the total weight of the composition, and more preferably from 1% to 10%.
  • the silicone film former of the present invention may be commercially available, and may come from suppliers in the form of a dilute solution. The amounts of the silicone film former disclosed herein therefore reflect the weight percent of active material.
  • the polyorganosilxane polymer and the film forming agent are solid. The composition is prepared by heating the solids sufficient to combine and form compositions as described herein. This combination of solid polyorganosilxane polymer and film forming agent provide beneficial transfer-resistant, long-wear compositions.
  • cosmetic compositions comprising at least one polyorganosiloxane containing polymer and at least one coloring agent are provided.
  • such colored cosmetic compositions are lip compositions (for example, lipstick or liquid lip colors) or foundations.
  • the at least one coloring agent is preferably chosen from pigments, dyes, such as liposoluble dyes, nacreous pigments, and pearling agents.
  • Representative liposoluble dyes which may be used according to the present invention include Sudan Red, DC Red 17, DC Green 6, ⁇ - carotene, soybean oil, Sudan Brown, DC Yellow 11 , DC Violet 2, DC Orange 5, annatto, and quinoline yellow.
  • the liposoluble dyes when present, generally have a concentration ranging up to 20% by weight of the total weight of the composition, such as from 0.0001 % to 6%.
  • the nacreous pigments which may be used according to the present invention may be chosen from white nacreous pigments such as mica coated with titanium or with bismuth oxychloride, colored nacreous pigments such as titanium mica with iron oxides, titanium mica with ferric blue or chromium oxide, titanium mica with an organic pigment chosen from those mentioned above, and nacreous pigments based on bismuth oxychloride.
  • the nacreous pigments if present, be present in the composition in a concentration ranging up to 50% by weight of the total weight of the composition, such as from 0.1% to 20%, preferably from 0.1% to 15%.
  • the pigments which may be used according to the present invention, may be chosen from white, colored, inorganic, organic, polymeric, nonpolymeric, coated and uncoated pigments.
  • Representative examples of mineral pigments include titanium dioxide, optionally surface-treated, zirconium oxide, zinc oxide, cerium oxide, iron oxides, chromium oxides, manganese violet, ultramarine blue, chromium hydrate, and ferric blue.
  • organic pigments include carbon black, pigments of D & C type, and lakes based on cochineal carmine, barium, strontium, calcium, and aluminum.
  • the pigments may be present in the composition in a concentration ranging up to 50 % by weight of the total weight of the composition, such as from 0,5% to 40%, and further such as from 2% to 30%.
  • the pigments, including nacreous pigments may, for example, represent up to 50% by weight of the composition.
  • the compositions comprising at least one polyorganosiloxane containing polymer are anhydrous.
  • the compositions comprising at least one polyorganosiloxane containing polymer further comprise water.
  • water is preferably present in an amount ranging from about 0.1 to about 70 %, preferably from about 0.5 to 50%, and more preferably from about 1 to about 30 % relative to the total weight of the composition.
  • water-containing cosmetic compositions are lip compositions (for example, lipstick or liquid lip colors), foundations or mascaras, and are emulsions or dispersions.
  • composition of the invention can also comprise any additive usually used in the field under consideration.
  • dispersants such as poly(12-hydroxystearic acid), antioxidants, essential oils, preserving agents, fragrances, waxes, liposoluble polymers that are dispersible in the medium, fillers, neutralizing agents, cosmetic and dermatological active agents such as, for example, emollients, moisturizers, vitamins, essential fatty acids, sunscreens, and mixtures thereof can be added.
  • suitable additional components can be found in the references which have been incorporated by reference in this application, including but not limited to the applications from which this application claims priority. Still further examples of such additional ingredients may be found in the International Cosmetic Ingredient Dictionary and Handbook (9 th ed. 2002).
  • An organogelator is defined herein to include a non-polymeric organic compound whose molecules may be capable of establishing, between themselves, at least one physical interaction leading to a self-aggregation of the molecules with formation of a macromolecular 3- D network which may be responsible for the gelation of the liquid fatty phase.
  • the network can result from the formation of a network of fibrils (due to the stacking or aggregation of organic-gelling molecules), immobilizing the molecules of the liquid fatty phase.
  • the interconnected fibrils have variable dimensions which may range up to one micron, or even several microns. These fibrils may occasionally combine to form strips or columns.
  • gelation means a thickening of the medium which may result in a gelatinous consistency and even in a solid, rigid consistency which does not flow under its own weight.
  • the ability to form this network of fibrils, and thus the gelation depends on the nature (or chemical category) of the organogelator, the nature of the substituents borne by its molecules for a given chemical category, and the nature of the liquid fatty phase. For example, this gelation is reversible.
  • the physical interactions are diverse but may exclude co- crystallization. These physical interactions are, for instance, interactions chosen from self-complementary hydrogen interactions, ⁇ interactions between unsaturated rings, dipolar interactions, and coordination bonding with organometallic derivatives.
  • each molecule of an organogelator can establish several types of physical interaction with a neighboring molecule.
  • the molecules of the organogelator according to the invention may comprise at least one group capable of establishing hydrogen bonding, e.g., at least two groups capable of forming hydrogen bonding; at least one aromatic ring, e.g., at least two aromatic rings; at least one bond with ethylenic unsaturation; and/or at least one asymmetric carbon.
  • the groups capable of forming hydrogen bonding may, for example, be chosen from hydroxyl, carbonyl, amine, carboxylic acid, amide and benzyl groups.
  • the at least one organogelator of the invention may be soluble in the liquid fatty phase at room temperature and atmospheric pressure. They may be solid or liquid at room temperature and atmospheric pressure.
  • Organogelator(s) which can be used in the invention are, for example, those described in the document "Specialist Surfactants" edited by D. Robb, 1997, pp. 209-263, chapter 8, by P. Terech, and the French patent application nos.
  • organogelators described in these documents are, for example, chosen from: [0216] - hydroxylated carboxylic fatty acids having a linear or branched aliphatic carbon chain containing, in one embodiment, at least 8 carbon atoms, such as at least 12 carbon atoms, for instance 12- hydroxystearic acid and 12-hydroxyoleic acid and salts thereof, such as alkali metal salts (in particular Li, Na and K salts) and alkaline-earth metal (for example Mg) salts or esters thereof resulting from esterification of a mono alcohol or polyol having a linear or cyclic, saturated or not chain with from 1 to 6 carbon atoms; [0217] - amides of carboxylic acids, such as tricarboxylic acids, for instance the cyclohexanetricarboxamides (
  • Ri and R 2 has the same meaning as defined in formula (VI). [0239] - bis oxalylamides of aminoacides such as those mentioned in the article M. JOKIC, J. chem. soc, chem.
  • R-i and R 2 may be identical or different, are a group chosen from -CH 2 -CH(CH 3 )2 ; -C6H 5 ; -CH 2 -CeH5 ; -CH(CH 3 ) 2 ; [0241] - amide and urea derivatives of lysine ester such as those mentioned in the article K.
  • F ⁇ -CH 3 or -C 2 H 5
  • R 2 -NH-(CH 2 ) 17 -CH 3
  • [0243] derivatives from diamides benzene dicarboxylic of acides and valine such as those mentioned in the article K. HANABUSA, Chemistry Letters, 767-8 (1999), the disclosure of which is herein incorporated by reference, and for example : [0244] in which -L-Val - represents : -NH-CH(CH(CH 3 ) 2 )-CO- ; [0245] -monoalkyloxamides such as those disclosed by X. LUO,
  • Ri and R 2 which can be identical or different are a hydrocarbon-based chain chosen from saturated or unsaturated linear, branched and cyclic hydrocarbon-based chains having 1 to 30 carbon atoms; [0247] - bolaamphiphiles having 1-glucosamide head, such as N, N'-bis( ⁇ -D-glucopyranosyl) alcane-1 , n-dicarboxamide, these compounds being mentioned in the article T. SHIMIZU, J. Am. Chem. Soc, 119, 2812- 18 (1997), the disclosure of which is herein incorporated by reference, and has the formula VIII :
  • n is an integer from 2 to 30
  • -alkyl-2-ammonium -2-isobutylacetate p-toluene sulfonate such as those disclosed by K. HANABUSA, Collo ⁇ d Polym. Sci, 276, 252-59 (1998), the disclosure of which is herein incorporated by reference, and having the formula XII : p-CH 3 -C 6 H 4 -SO 3 - + H 3 N-CH(R ⁇ )-CO-OR 2 (XII)
  • Ri - CH 2 -CH(CH 3 ) 2 ; -CH(CH 3 ) 2 ; -CH(CH 3 )-CH 2 - CH 3 ; -CH 2 -C 6 H 5 - CH 2 -CH 2 -CO-O-CH 2 -(CH 2 ) ⁇ o-CH 3
  • R 2 -CH 2 -(CH 2 ) n -CH 3 with n an integer from 4 to 12.
  • cellobiose fatty esters such a those mentioned in WO-A- 00/61080, the disclosure of which is herein incorporated by reference, and WO-A-00/61081 , the disclosure of which is herein incorporated by reference, and having the formula XIII :
  • diamides having the formula XIV or XV R 2 -X-CO-NH-R NH-CO-X-R 2 (XIV) or
  • Ri is alkylene group chosen from C ⁇ -C 50 linear, branched and cyclic groups and C 5 -Cs arylene groups and alkylen groups comprising C 1 -C 4 alkyl group ; and in which -X- represents -O- or -NH- ; and in which R 2 , which may be identical or different is a Ca-C 6 o saturated or unsaturated linear or branched hydrocarbon-based chain, at least one R 2 comprising optionally a hydroxyl group or at least one hetero atom such as N, O, S or Si. [0255] - and mixtures thereof.
  • the organogelator may be a compound of formula (II) below: R-CO-NH-A-NH-CO-R' [0259] in which: [0260] - R and R', which may be identical or different, are chosen from a hydrogen atom and hydrocarbon-based chains chosen from saturated linear, saturated branched, saturated cyclic, unsaturated linear, unsaturated branched and unsaturated cyclic hydrocarbon-based chains containing from 1 to 22 carbon atoms, for example from 6 to 18 carbon atoms, such as from 10 to 14 carbon atoms, optionally substituted with at least one group chosen from aryl (-C 6 H 5 ), ester (-COOR" with R" being an alkyl group containing 2 to 12 carbon
  • A is chosen from saturated and unsaturated, linear, cyclic and branched hydrocarbon-based chains containing from 1 to 18 carbon atoms, such as from 2 to 12 carbon atoms, and for example from 4 to 12 carbon atoms, optionally substituted with at least one group chosen from aryl (- C 6 H 5 ), ester [0263] (-COOR” with R" being an alkyl group containing from 2 to 12 carbon atoms), amide (-CONHR” with R” being an alkyl group containing from 2 to 12 carbon atoms), urethane (-OCONHR” with R" being an alkyl group containing from 2 to 12 carbon atoms) and urea (-NHCONHR” with R" being an alkyl group containing from 2 to 12 carbon atoms) groups; and/or optionally containing from 1 to 3 hetero atoms chosen from O, S and N; and/or optionally substituted with from 1 to 4 halogen atoms, such as fluorine atoms,
  • the compounds correspond to the formula (II) in which: [0266] - A is chosen from saturated and unsaturated but non- aromatic, optionally branched hydrocarbon-based rings containing from 4 to 12 carbon atoms, for example from 5 to 7 carbon atoms, optionally substituted with the substituents mentioned above and/or optionally comprising at least one hetero atom and/or optionally substituted with at least one halogen and/or hydroxyl radical; [0267] - R and R', which may be identical or different, are chosen from a hydrogen atom and hydrocarbon-based chains chosen from saturated linear, saturated branched, saturated cyclic, unsaturated linear, unsaturated branched and unsaturated cyclic hydrocarbon-based chains containing from 10 to 16 carbon atoms, for example, from 12 to 14 carbon atoms, such as a saturated, linear hydrocarbon-based chain; or [0268] - A is a saturated hydrocarbon-based chain chosen from linear and branched saturated hydrocarbon-based chains
  • the radical A may be, for example, a divalent radical such as cyclohexylene, ethylene, propylene, isopropylene, butylene, isobutylene, pentylene, hexylene, dodecylene, dodecanylene, benzylene, phenylene, methylphenylene, bis-phenylene or naphthalene.
  • a divalent radical such as cyclohexylene, ethylene, propylene, isopropylene, butylene, isobutylene, pentylene, hexylene, dodecylene, dodecanylene, benzylene, phenylene, methylphenylene, bis-phenylene or naphthalene.
  • R and R' may be chosen, independently of each other, from, for example, pentyl, hexyl, decyl, undecyl, dodecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, 3-dodecyloxypropionyl, 3-octadecyloxy- propionyl, 3-dodecyloxypentyl, 3-octadecyloxypentyl and 11- hydroxyheptadecyl radicals.
  • R and R' are identical.
  • the radicals R-CO-NH- and R'- CO-NH- may be in an ortho, meta or para position. Moreover, they may be in a cis or trans position relative to each other.
  • the compounds of formula (II) is a mixture of cis and trans compounds.
  • the compounds of formula (II) may be chosen from the compounds corresponding to one of the following formulae:
  • the compounds of formula (II) can be prepared according to processes that are well known to those skilled in the art. [0288] In particular, they may be obtained by reacting a diamine H 2 N-A-NH 2 with an acid chloride RCOCI and/or R'COCI with R and R' having the above meaning, but other than a hydrogen atom, in an organic solvent medium which is compatible for carrying out the reaction (1 mol of acid chloride is used per 1 mol of diamine if it is desired to obtain a compound of formula (I) containing only one group R other than a hydrogen atom, or 2 mol of acid chloride RCOCI and/or R'COCI if it is desired to obtain a compound of formula (II) with R and R' other than a hydrogen atom).
  • the reaction is preferably carried out in the presence of a base capable of neutralizing the formation of the HCl released during the reaction.
  • the diamide formed is extracted from the reaction medium according to the conventional extraction techniques that are well known to those skilled in the art.
  • the compounds of formula (II) can be prepared according to processes that are well known to those skilled in the art and can be used, alone or as a mixture, in the composition of the invention.
  • Standard preparation of the compounds of formula (II) for R R'
  • the diamine and two equivalents of triethylamine are dissolved in 50 ml of tetrahydrofuran.
  • R is identical or different and each is chosen from a hydrogen atom, a saturated linear hydrocarbon-based chain, and a saturated branched hydrocarbon-based chain, wherein said hydrocarbon-based chains contain from 1 to 6 carbon atoms, for example from 1 to 4 carbon atoms;
  • Y is identical or different and each is a group chosen from the following groups: -CO-S-R'; -CO-NHR'; -NH-COR' and -S-COR'; in which R' is identical or different and each is chosen from: [0296] - a hydrogen atom; [0297] - an aryl group; [0298] - an aralkyl group, i.e., an aryl group substituted with a hydrocarbon-based chain chosen from saturated, linear hydrocarbon-based chains and saturated, branched hydrocarbon-based chains, wherein the hydrocarbon based chain contains from 1 to 22 carbon atoms, for example from 10 to 18
  • R for example, is chosen from a hydrogen atom.
  • Y for example, is chosen from the groups -CO-NHR' and -NH- COR'.
  • R' for example, is chosen from an aryl group; an aralkyl group in which the linear or branched alkyl chain contains from 12-16 carbon atoms; and a linear or branched Cn-C-ie alkyl chain.
  • Y is chosen from a group -CO-NHR' in which R' is chosen from an aryl group substituted with a C- ⁇ 2 -C ⁇ 6 alkyl chain chosen from linear and branched Cn-C ⁇ 6 alkyl chains; or R' is chosen from an unsubstituted linear C- ⁇ -Cis alkyl chain and an unsubstituted branched Cn-Ci ⁇ alkyl chain.
  • the three substitutents represented by Y can be, in the compounds of formula (III), in cis-cis, cis-trans or trans-trans conformation relative to each other.
  • the compounds of formula (III) is a mixture of cis-cis, cis-trans and/or trans-trans compounds.
  • Such compounds include urea urethanes having the following formula: R-O-CO-NH-R'-NH-CO-NH-R"-NH-CO-NH-R'-NH-CO-OR [0313] wherein R represents C n H n +i- or C m H 2m + ⁇ (CpH 2p O) r -; n represents an integer having a value of from 4 to 22; m represents an integer having a value of from 1 to 18; p represents an integer having a value of from 2 to 4; and r represents an integer having a value of from 1 to 10, [0314] R' represents: or — (CH 2 ) 6 — [0315] and R" represents:
  • the organogelator may be at least one organogelator of formula (IV); RNHCONHANHCONHR [0319] wherein A and R have the same definition as the one provided above for formula (II), expressed most broadly as: [0320]
  • R which may be identical or different, is each chosen from a hydrogen atom and hydrocarbon-based chains chosen from saturated linear, saturated branched, saturated cyclic, unsaturated linear, unsaturated branched and unsaturated cyclic hydrocarbon-based chains containing from 1 to 22 carbon atoms, for example from 6 to 18 carbon atoms, optionally substituted with at least one group chosen from aryl (-C 6 H 5 ), ester (-COOR” with R" being an alkyl group containing from 2 to 12 carbon atoms), amide (- CONHR” with R" being an alkyl group containing from 2 to 12 carbon atoms), urethane (-OCONHR" with R" being an alkyl group containing from 2 to 12 carbon atom
  • the inventive composition contains from 0.1% to 80% by weight of organogelator. In another embodiment, the composition contains from 0.5% to 60% by weight of organogelator, for example, from 1 % to 40% or from 2% to 30%, including all values and ranges there between.
  • Active Agents [0326]
  • the composition of the present invention advantageously contains at least one cosmetic active agent and/or at least one dermatological active agent, i.e., an agent having a beneficial effect on the skin, lips or body growths and/or at least one coloring agent.
  • Gelling Agent [0328] The composition of the invention may also contain at least one agent useful for gelling a liquid fatty phase.
  • the gelling agent increases the liquid fatty phase viscosity and leads to a solid or flowable composition when introduced in said fatty phase.
  • the gelling agent does not encompass waxes, in the sense that it is not waxy.
  • the at least one gelling agent may be chosen from gelling agents in polymeric form and gelling agents in mineral form.
  • the at least one gelling agent is not soluble in an aqueous phase or in water.
  • the gelling agent according to the present invention is preferably selected from the group consisting of agents that gel via chemical reticulation and agents that gel via physical reticulation.
  • crosslinked elastomeric polyorganosiloxanes of three-dimensional structure are preferred. These elastomeric silicones can bear hydrophile groups, such as polyoxyethylene or copoly(oxyethylene/oxypropylene).
  • hydrophile groups such as polyoxyethylene or copoly(oxyethylene/oxypropylene).
  • radicals R independently of each other, are chosen from a hydrogen, an alkyl such as methyl, ethyl or propyl, an aryl such as phenyl or tolyl, an unsaturated aliphatic group such as vinyl, the weight ratio of the units R 2 SiO to the units RSiO ⁇ .
  • polyorganosiloxanes which are insoluble and swellable in silicone oil, obtained by addition of an polyorganohydrogenosiloxane (1 ) and of a polyorganosiloxane (2) having unsaturated aliphatic groups such that the amount of hydrogen or of unsaturated aliphatic groups in (1) and (2) respectively ranges from 1 to 20 mol% when the polyorganosiloxane is non- cyclic and from 1 to 50 mol% when the polyorganosiloxane is cyclic.
  • these polyorganosiloxanes can comprise from 1 to 40 oxyalkylene groups, such as oxypropylene and/or oxyethylene groups.
  • elastomeric polyorganosiloxanes which can be used according to the invention, mention may be made of those sold or made under the names KSG6 from Shin-Etsu, Trefil E-505C or Trefil E- 506C from Dow-Corning, Gransil from Grant Industries (SR-CYC, SR DMF10, SR-DC556) or those marketed in the form of preconstituted gels (KSG15, KSG17, KSG16, KSG18, KSG21 from Shin-Etsu, Gransil SR 5CYC gel, Gransil SR DMF 10 gel, Gransil SR DC556 gel, SF 1204 and JK 113 from General Electric or emulsifying elastomers such as those sold under the names of KSG-210, KSG-30, KSG-31 , KSG-32, KSG-33, KSG-40, KSG 41 , KSG-42, KSG-43 and KSG-44 from Shin-Etsu.
  • KSG6 from Shin
  • Gelling agents that gel via physical reticulation are preferred.
  • Gelling agents that gel via molecular muddling are polymers having high molecular weights, preferably higher than 500 000, such as silicone gums.
  • the silicone gum can correspond to the formula:
  • R , Rs, R 1 1 and R ⁇ 2 are identical or different, and each is chosen from alkyl radicals comprising from 1 to 6 carbon atoms
  • Rg and R-io are identical or different, and each is chosen from alkyl radicals comprising from 1 to 6 carbon atoms and aryl radicals
  • X is chosen from alkyl radicals comprising from 1 to 6 carbon atoms, a hydroxyl radical and a vinyl radical
  • n and p are chosen so as to give the silicone gum a viscosity of greater than 100 000 mPa.s, such as greater than 500 000 mPa.s.
  • n and p can each take values ranging from 0 to 5 000, such as from 0 to 3 000.
  • the substituents R 7 to R- 1 2 and X represent a methyl group
  • the substituents R 7 to R 12 and X represent a methyl group
  • the substituents R 7 to R 12 represent a methyl group
  • the substituent X represents a hydroxyl group
  • the terminal Si's can also be other than methyl and may be represented with substitutions on the repeating Si such that the R group is an alkyl of 1 to 6 carbon atoms , which may be linear, branched and/or functionalized selected from methyl, ethyl, propyl, isopropyl, butyl, isobutyl, t-butyl, amyl, hexyl, vinyl, allyl, cycohexyl, phenyl, fluoroalkyl, and mixtures thereof.
  • the R group is an alkyl of 1 to 6 carbon atoms , which may be linear, branched and/or functionalized selected from methyl, ethyl, propyl, isopropyl, butyl, isobutyl, t-butyl, amyl, hexyl, vinyl, allyl, cycohexyl, phenyl, fluoroalkyl, and mixtures thereof.
  • the silicone gums employed in the present invention may be terminated by triorganosilyl groups of the formula R' 3 where R' is a radical of monovalent hydrocarbons containing from 1 to 6 carbon atoms, hydroxyl groups, alkoxyl groups and mixtures thereof.
  • R' is a radical of monovalent hydrocarbons containing from 1 to 6 carbon atoms, hydroxyl groups, alkoxyl groups and mixtures thereof.
  • the silicone gums used in the invention have an affinity with the structuring polymer and/or with the silicone gum, and the liquid fatty phase, the polymer and the silicone gum form a physiologically acceptable medium.
  • a particularly preferred fluid diorganopolysiloxane polymer is poly(dimethylsiloxane), herein referred to as PDMS.
  • crystalline silicone compounds are included in the compositions.
  • a crystalline silicone compound is a compound comprising silicone in its molecule, which is solid at room temperature, and has a crystalline character. This compound or class of compounds is compatible with the liquid fatty phase and the structuring agent.
  • the crystalline silicone compounds belong to a class of alkyl siloxane waxes corresponding to the formulae below:
  • Examples of crystalline silicone compounds include, but are not limited to, C20-24 Alkyl Methicone, C24-28 Alkyl Dimethicone, C20-24 Alkyl Dimethicone, C24-28 Alkyl Dimethicone commercially available from Archimica Fine Chemicals, Gainesville, FL under the designation of SilCare 41 M40, SilCare 41 M50, SilCare 41 M70 and SilCare 41 M80. Stearyl Dimethicone available as SilCare 41M65 from Archimica or as DC-2503 from Dow-Corning, Midland, Michigan. Similarly, stearoxytrimethylsilane sold as SilCare 1M71 or DC-580 may be used in an embodiment of this invention.
  • crystalline silicone compounds are available from Degussa Care Specialties, Hopewell, VA under the designation ABIL Wax 9810, 9800, or 2440, orWacker-Chemie GmbH, Burghausen, Germany, under the designation BelSil SDM 5055, or OSi Specialties, Greenwich, CT under the designation Silsoft.
  • Other crystalline silicone compounds include C30-45 Alkyl Methicone available from Dow Corning as AMS-C30 Wax, as well as GE's SF1642, or SF-1632 available from General Electric, Fairfield, CT.
  • Gelling agents that gel the liquid fatty phase via hydrogen interactions are preferably chosen in the group consisting of: [0365] amino silicones polymers having triazinyl groups or pyrimidinyl groups bound to amino groups of amino silicones as described in patent application EP 0 751 170, the disclosure of which is incorporated herein by reference, [0366] non-silicone polyamides, ends of which bear ester or triamides functions, such as compounds described in patents and patent applications US 5 783 657, US 6 268 466, WO 01/95871 , WO 00/40216, US 2002/0035237, and EP 1 068 856 , the disclosure of which are incorporated herein by reference, [0367] polyurethanes, such as compounds described in patent applications DE 10022247 and FR 2 814 365, the disclosure of which are incorporated herein by reference, and [0368] vinyl and/or (meth)acrylic polymers bearing lateral groups that can create mutual hydrogen interactions, such as compounds described in
  • Gelling agents that gel the liquid fatty phase via sequences incompatibility are preferably selected from the group consisting of: [0370] block (di ou tri blocks) copolymers, such as polystyrene-silicone, or polyethylene-silicone, described in patents US 6 225 390, US 6 160 054, US 6 174 968 and US 6 225 390, the disclosures of which are incorporated herein by reference, [0371] block or grafted copolymers comprising a silicone sequence and another sequence or graft that is polyvinyl or poly(meth)acrylic, such as those described in patents US 5 468 477 et US 5 725 882, the disclosures of which are incorporated herein by reference.
  • block (di ou tri blocks) copolymers such as polystyrene-silicone, or polyethylene-silicone, described in patents US 6 225 390, US 6 160 054, US 6 174 968 and US 6 225 390, the
  • polymers or copolymers resulting from the polymerization or copolymerization of an ethylenic monomer comprising one or more ethylenic, preferably conjugated, bonds (or dienes)
  • polymers or copolymers resulting from the polymerization or copolymerization of an ethylenic monomer in particular use may be made of vinyl, acrylic or methacrylic copolymers which may be block copolymers, such as diblock or triblock copolymers, or even multiblock or starburst or radial copolymers.
  • the at least one ethylenic gelling agent may comprise, for example, a styrene block (S), an alkylstyrene block (AS), an ethylene/butylene block (EB), an ethylene/propylene block (EP), a butadiene block (B), an isoprene block (I), an acrylate block (A), a methacrylate block (MA) or a combination of these blocks.
  • a copolymer comprising at least one styrene block is used as gelling agent or ethylenic Theological agent.
  • ethylenical gelling agent which can be used in the composition of the invention, mention may be made, for example, of Kraton (G1650 (SEBS), Kraton G1651 (SEBS), Kraton G1652 (SEBS), Kraton G1657X (SEBS), Kraton G1701X (SEP), Kraton G1702X (SEP), Kraton G1726X (SEB), Kraton G1750X (EP) multiarm, Kraton G1765X (EP) multiarm, Kraton D-1101 (SBS), Kraton D-1102 (SBS), Kraton D-1107 (SIS), Gelled Permethyl 99A - 750, Gelled Permethyl 99A- 753-58 (mixture of starburst block polymer and triblock polymer), Gelled Permethyl 99A- 753- 59 (mixture of starburst block polymer and triblock polymer), Versagel 5970 and Versagel 5960 from Penreco (mixture of starburs
  • Di or triblocks such as polystyrene-copoly(ethylene/propylene) or polystyrene-copoly(ethylene/butylene) such as those described in patent applications WO 98/38981 and US 2002/0055562, the disclosures of which are hereby incorporated by reference, are also included in the present invention.
  • Gelling agents that gel via dipolar interactions are preferably chosen from compounds describes in documents WO 01/30886 et US 6 228 967, the disclosures of which are incorporated herein by reference. Ionized groups of said compounds, for example zwitterionic groups, create said dipolar interactions.
  • Gelling agents such as liposoluble polymers having liquid crystal groups are also preferred according to the present invention, especially liposoluble polymers whose backbone is silicone, vinyl and/or (meth)acryiic and that possess des lateral liquid crystal groups, in particular compounds described in patent application FR 2 816 503, the disclosure of which is incorporated herein by reference.
  • the at least one gelling agent may be in mineral form with particle sizes that cause little or no light scattering. Thus, it may be possible to obtain a translucent or even transparent composition.
  • modified clays which can be used, mention may be made of hectorites modified with an ammonium chloride of a C ⁇ o to C 22 fatty acid, such as hectorite modified with distearyldimethylammonium chloride, also known as quatermium-18 bentonite, such as the products sold or made under the names Bentone 34 by the company Rheox, Claytone XL, Claytone 34 and Claytone 40 sold or made by the company Southern Clay, the modified clays known under the name quaternium-18 benzalkonium bentonites and sold or made under the names Claytone HT, Claytone GR and Claytone PS by the company Southern Clay, the clays modified with stearyldimethylbenzoylammonium chloride, known as steralkonium bentonites, such as the products sold or made under the names Claytone APA and Claytone AF by the company Southern Clay, and Baragel 24 sold or made by the company Rheox.
  • silica such as fumed silica.
  • the fumed silica may have a particle size, which may be nanometric to micrometric, for example ranging from about 5 nm to 200 nm.
  • the fumed silicas may be obtained by high-temperature hydrolysis of a volatile silicon compound in a hydrogen-oxygen flame, producing a finely divided silica. This process makes it possible to obtain hydrophilic silicas that have a large number of silanol groups at their surface.
  • hydrophilic silicas are sold or made, for example, under the names “Aerosil 130®”, “Aerosil 200®”, “Aerosil 255®”, “Aerosil 300®” and “Aerosil 380®” by the company Degussa, and "CAB-O-SIL HS-5®”, “CAB-O- SIL EH-5®”, “CAB-O-SIL LM-130®”, “CAB-O-SIL MS-55®” and “CAB-O-SIL M-5®” by the company Cabot. [0383] It is thus possible to chemically modify the surface of the hydrophilic silica by chemical reaction, producing a reduction in the number of silanol groups.
  • the silanol groups can be replaced, for example, with hydrophobic groups: this then gives a hydrophobic silica.
  • the hydrophobic groups may be: [0384] trimethylsiloxyl groups, which are obtained in particular by treating fumed silica in the presence of hexamethyldisilazane. Silicas thus treated are known as "silica silylate" according to the CTFA (6th edition, 1995).
  • hydrophobic silica such as fumed silica, may be used as lipophilic gelling agent.
  • the use of fumed silica makes it possible to obtain a translucent or even transparent composition, in particular in the form of a stick, which does not exude, in the absence of opacifying particles such as waxes, fillers and pigments (including nacres).
  • the at least one liposoluble gelling agent can allow the exudation of the composition to be limited and can allow its stability to be increased, while at the same time conserving the composition's glossy appearance, which is not possible with waxes such as those used conventionally in cosmetics and dermatology.
  • These gelling agents can be used, for example, at concentrations of from 0.05% to 35% relative to the total weight of the composition, for example from 0.5% to 20% or from 1% to 10%.
  • esters may be included in the compositions of the present invention.
  • the esters may either be monoesters, diesters or polyesters. These esters may be linear, branched or cyclic, saturated or unsaturated. These esters should preferably be branched and saturated. They may also be aliphatic or aromatic. [0391] These esters may have from 6 to 25 carbon atoms and particularly from 14 to 22 carbon atoms.
  • esters may be chosen amongst acid esters having from 2 to 18 carbon atoms, and particularly amongst alcohol esters having from 2 to 20 carbon atoms or amongst polyols having from 2 to 8 carbon atoms or their mixtures, on condition that the number of carbon atoms is higher than 10, so that the ester is not volatile and penetrates the skin.
  • these esters are hydrocarbon-based esters which correspond to the following formula RCOOR' where R represents a residue of fatty acid having from 1 to 29 carbon atoms, and R' represents a hydrocarbon-based chain containing from 2 to 30 carbon atoms, on condition that the number of carbon atoms in R' is higher than 10, so that the ester is not volatile and penetrates the skin.
  • the ester may be chosen among a non-limitative list including the following: [0394] Neopentanoic acid esters such as isodecyl neopentanoate, isotridecyl neopentanoate, isostearyl neopentanoate, octyldocecyl neopentanoate, [0395] Isononanoic acid esters such as isononyl isononanoate, octyl isononanoate, isodecyl isononanoate, isotridecyl isononanoate, isostearyl isononanoate, ethylhexyl isononanoate, [0396] Isopropylic alcohol esters, such as isopropyl myristate, isopropyl palmitate, isopropyl stearate or isostearate, isopropyl laurate,
  • Examples of short chain esters also include purcellin oil (cetostearyl octanoate), ethylhexyl ethylhexanoate, dicapryl ester, 2- ethylhexyl palmitate, 2-ethyl-palmitate and isostearyl isostearate.
  • the isononyl isononanoate and diisostearyl malate are particularly suited for the embodiment of this invention.
  • This or these hydrocarbon-based ester(s) may be used in the composition at a percentage of 5 to 90%, notably of 10 to 60%, particularly of 20 to 50% by weight of the total weight of the composition.
  • the mass ratio between the short chain ester, if present, and the polyorganosiloxane containing polymer is preferably between 1/4 and 2/1 , more preferably between 1/3 and 1/1.
  • Additional ingredients which offer similar cosmetic properties as the short chain esters are short chain ethers which may be represented as J-O-K [0407] where J and K are identical or different and represent a linear or branched alkyl radical from 1 to 40 carbon atoms, preferably from 7 to 19 carbon atoms, possibly including one or more double bonds.
  • An example of such an ether includes dicapryl ether.
  • the composition can optionally contain one or more waxes to improve the structuring in stick form, although this rigid form can be obtained in the absence of wax.
  • a wax is a lipophilic fatty compound that is solid at room temperature (25°C) and atmospheric pressure (760 mmHg, i.e. 101 KPa), which undergoes a reversible solid/liquid change of state, having a melting point of greater than 40°C and further such as greater than 55°C and which may be up to 200°C, and having an anisotropic crystal organization in the solid state.
  • the size of the crystals is such that the crystals diffract and/or scatter light, giving the composition a cloudy, more or less opaque appearance.
  • the composition advantageously contains little or no wax, and in particular less than 5% wax.
  • the waxes are those generally used in cosmetics and dermatology; they are, for example, of natural origin, for instance beeswax, carnauba wax, candelilla wax, ouricury wax, Japan wax, cork fiber wax, sugar cane wax, paraffin wax, lignite wax, microcrystalline waxes, lanolin wax, montan wax, ozokerites and hydrogenated oils such as hydrogenated jojoba oil as well as waxes of synthetic origin, for instance polyethylene waxes derived from the polymerization of ethylene, waxes obtained by Fischer-Tropsch synthesis, fatty acid esters and glycerides that are solid at 40°C, for example, at above 55°C, silicone waxes such as alkyl- and alkoxy-poly(di)methylsiloxanes and/or poly(di)methyl-siloxane esters that are solid at 40°C, for example, at above 55°C.
  • natural origin for instance beeswax, carnauba wax
  • the melting point values correspond to the melting peak measured by the "Differential Scanning Calorimetry" method with a temperature rise of 5 or 10°C/min.
  • Liposoluble or Dispersible Polymers [0413]
  • the composition of the invention also can contain at least one polymer that is liposoluble or dispersible in the medium, other than the polyorganosiloxane containing polymer, and may have film-forming properties and may have, for example, an average molecular weight of from 500 to 1 ,000,000, such as from 1 ,000 to 500,000, and for example, further such as from 5,000 to 100,000, and even further such as from 5,000 to 20,000.
  • This at least one liposoluble polymer may contribute towards increasing the viscosity and/or improving the staying power of the film.
  • the at least one liposoluble polymer can have a softening point of not more than 30°C.
  • liposoluble polymers which can be used in the invention, mention may be made of: polyalkylenes, in particular polybutene, poly(meth)acrylates, alkylcelluloses with a linear or branched, saturated or unsaturated Ci to Cs alkyl radical, such as ethylcellulose and propylcellulose, silicone polymers that are compatible with the fatty phase, as well as vinylpyrrolidone (VP) copolymers, and mixtures thereof.
  • Vinylpyrrolidone copolymers can be used.
  • VP copolymers which can be used in the invention, mention may be made of VP/vinyl acetate, VP/ethyl methacrylate, butylated polyvinylpyrrolidone (PVP), VP/ethyl methacrylate/methacrylic acid, VP/eicosene, VP/hexadecene, VP/triacontene, VP/styrene or VP/acrylic acid/lauryl methacrylate copolymer.
  • PVP polyvinylpyrrolidone
  • the PVP/hexadecene copolymer having an average molecular weight of from 7,000 to 7,500 or alternatively the PVP/eicosene copolymer having an average molecular weight of from 8,000 to 9,000 can be used.
  • the liposoluble or dispersible polymers in the composition of the invention can be also used in an amount of from 0.01 % to 20% (as active material) relative to the total weight of the composition, such as, for example, from 1 % to 10%, if they are present.
  • Emollients and/or humectants that may be used in the compositions of the invention include glycerin, propylene glycol, and emollients and other similar ingredients disclosed in the International Cosmetic Ingredient Dictionary and Handbook Vol. 4 (9 th ed. 2002), more particularly the emollients disclosed on pages 2930-2936. The disclosure of the International Cosmetic Ingredient Dictionary and Handbook Vol. 4, pages 2930-2936, is hereby incorporated by reference.
  • Surfactants [0421]
  • the compositions of the invention may further include formulation aids which are usually employed in the field of application envisaged.
  • the formulation aids used in the present invention can be, but are not limited to, surfactants.
  • Useful surfactants include, but are not limited to, organic and organosilicone emulsifiers for water-in-oil systems.
  • organic emulsifiers include any ethoxylated surfactants known in the art such as Polysorbate-20, Laureth-7, Laureth-4, Sepigel® 305 available from SEPPIC and other similar ingredients disclosed in the International Cosmetic Ingredient Dictionary and Handbook Vol. 4 (9 th ed. 2002), more particularly the emulsifiers disclosed on pages 2962-2971.
  • the disclosure of the International Cosmetic Ingredient Dictionary and Handbook Vol. 4, pages 2962-2971 is hereby incorporated by reference.
  • organosilicone emulsifiers include cetyl dimethicone copolyol-polyglyceryl-4- isostearate-hexylaurate (ABIL® WE 09) available from Goldschmidt Chemical Corporation, Cetyl Dimethicone Copolyol (ABIL® EM 90), (ABIL® EM 97), Laurylmethicone Copolyol (5200), Cyclomethicone (and) Dimethicone Copolyol (DC 5225 C and DC 3225 C) available from GE Silicones, Cyclopentasiloxane & Dimethicone Copolyol (GE SF 1528) or any other formulation aids known by one of skill in the art.
  • ABIL® WE 09 available from Goldschmidt Chemical Corporation
  • Cetyl Dimethicone Copolyol (ABIL® EM 90), (ABIL® EM 97), Laurylmethicone Copolyol (5200), Cyclomethicon
  • Plasticizers may also be added to the compositions to improve the flexibility and cosmetic properties of the resulting formulation.
  • Plasticizers are materials which soften synthetic polymers. They are frequently required to avoid brittleness and cracking of film formers.
  • One skilled in the art may routinely vary the amount of plasticizer desired based on the properties desired and the application envisaged.
  • Plasticizers useful in the practice of the invention include lecithin, polysorbates, dimethicone copolyol, glycols, citrate esters, glycerin, dimethicone, and other similar ingredients disclosed in the International Cosmetic Ingredient Dictionary and Handbook Vol. 4 (9 th ed. 2002), more particularly the plasticizers disclosed on page 2927.
  • the composition may contain sunscreens.
  • the combination of the polysiloxane-containing polymer when combined with one or more sunscreens improves, quite significantly, the overall SPF value of the composition relative to a composition without the polysiloxane-containing polymer.
  • Sunscreens may be inorganic nanoparticles or organic compounds. In one embodiment the nanoparticles are inorganic compounds composed essentially of metal oxides.
  • Suitable metal oxides comprise one or more of iron oxide, aluminum oxide, zirconium oxide, vanadium oxide, niobium oxide, tantalum oxide, chromium oxide, molybdenum oxide, tungsten oxide, cobalt oxide, nickel oxide, cerium cupric oxide, zinc oxide, tin oxide, antimony oxide titanium dioxide and mixtures thereof, among others. In yet another embodiment titanium dioxide and zinc oxide are used. Without being limited to theory, in most cases the metal oxide nanoparticles provide a sun protection benefit by diffracting the ultraviolet light.
  • the elemental size of 1 nanoparticle is typically from less than 1 ⁇ m in size, including from about 100 nm to about 500 nm, including about 200 nm to about 350 nm.
  • UV-A absorbers generally absorb radiation in the 320 to 400 nm region of the ultraviolet spectrum.
  • UV-A absorbers include anthranilates, benzophenones, and dibenzoyl methanes.
  • UV-B absorbers generally absorb radiation in the 280 to 320 nm region of the ultraviolet spectrum.
  • UV-B absorbers include p- aminobenzoic acid derivatives, camphor derivatives, cinnamates, and salicylates.
  • UV-A or UV-B absorbers Classifying the chemical absorbers generally as UV-A or UV-B absorbers is accepted within the industry. However, a more precise classification is one based upon the chemical properties of the sunscreens. There are eight major classifications of sunscreen chemical properties which are discussed at length in “Sunscreens - Development, Evaluation and Regulatory Aspects,” by N. Shaath et al., 2nd. Edition, pages 269-273, Marcel Dekker, Inc. (1997). This discussion, in its entirety, is incorporated by reference herein. [0429] The sunscreens which may be formulated according to the present invention typically comprise chemical absorbers, but may also comprise physical blockers.
  • Exemplary sunscreens which may be formulated into the compositions of the present invention are chemical absorbers such as p-aminobenzoic acid derivatives, anthranilates, benzophenones, camphor derivatives, cinnamic derivatives, dibenzoyl methanes, diphenylacrylate derivatives, salicylic derivatives, triazine derivatives, benzimidazole compounds, bis-benzoazolyl derivatives, methylene bis-(hydroxyphenylbenzotriazole) compounds, the sunscreen polymers and silicones, or mixtures thereof.
  • chemical absorbers such as p-aminobenzoic acid derivatives, anthranilates, benzophenones, camphor derivatives, cinnamic derivatives, dibenzoyl methanes, diphenylacrylate derivatives, salicylic derivatives, triazine derivatives, benzimidazole compounds, bis-benzoazolyl derivatives, methylene bis-(hydroxyphenylbenzotriazole
  • Non-limiting examples of sunscreens which may be formulated into the compositions of the instant invention include those selected from among: aminobenzoic acid, amyldimethyl PABA, cinoxate, diethanolamine p-methoxycinnamate, digalloyl trioleate, dioxybenzone, 2-ethoxyethyl p- methoxycinnamate, ethyl 4-bis(hydroxypropyl)aminobenzoate, 2-ethylhexyl- 2-cyano-3,3-diphenylacrylate, ethylhexyl p-methoxycinnamate, 2-ethylhexyl salicylate, glyceryl aminobenzoate, homomenthyl salicylate, homosalate, 3- imidazol-4-ylacrylic acid and ethyl ester, methyl anthranilate, octyldimethyl PABA, 2-phenylbenzimidazole-5-sulfonic acid
  • Sunscreens active in the UV-A and/or UV-B range can also include: p-aminobenzoic acid, oxyethylene (25 mol) p-aminobenzoate, 2-ethylhexyl p-dimethylaminobenzoate, ethyl N-oxypropylene p-aminobenzoate, glycerol p-aminobenzoate, 4-isopropyl benzyl salicylate, 2-ethylhexyl 4-methoxycinnamate, methyl diisopropylcinnamate, isoamyl 4-methoxycinnamate, diethanolamine 4-methoxycinnamate, 3-(4 , -trimethylammunium)-benzyliden-boman-2-one methylsulfate, 2-hydroxy-4-methoxybenzophenone, 2-hydroxy-4-methoxybenzophenone-5-sulfonate, 2,4-dihydroxybenzophenone
  • Patent No. 4,585,597 issued to Lange et al. on April 29, 1986, hereby incorporated by reference), urocanic acid, 2,4,6-tris[p-(2'-ethylhexyl-1'-oxycarbonyl)-anilino]-1 ,3,5-triazine, 2-[(p-(tertiobutylamido)anilino]-4,6-bis-[(p-(2'-ethylhexyl-1'- oxycarbonyl)anilino]-1 ,3,5-triazine, 2,4-bis ⁇ [4-(2-ethyl-hexyloxy)]-2-hydroxy]-phenyl ⁇ -6-(4-methoxy-phenyl)- 1 ,3,5-triazine ("TINOSORB S" marketed by Ciba), the polymer of N-(2 et 4)-[(2-oxoborn-3-yliden)methyl]benzyl]-
  • dibenzoyl methane sunscreens other than avobenzone include (whether singly or in any combination): 2-methyldibenzoylmethane 4-methyldibenzoylmethane 4-isopropyldibenzoylmethane 4-tert.-butyldibenzoylmethane 2,4-dimethyldibenzoylmethane 2,5-dimethyldibenzoylmethane 4,4'-diisopropyldibenzoylmethane 4,4'-dimethoxydibenzoylmethane 2-methyl-5-isopropyl-4'-methoxydibenzoylmethane 2-methyl-5-tert.-butyl-4'-methoxydibenzoylmethane 2,4-dimethyl-4'-methoxydibenzoylmethane 2,6-dimethyl-4-tert.-butyl-4'-methoxydibenzoylmethane
  • compositions according to the invention are generally present in the compositions according to the invention in proportions ranging from 0.1 to 30% by weight with respect to the total weight of the composition and preferably ranging from 0.2 to 15% by weight with respect to the total weight of the composition.
  • Compositions of the invention preferably have a SPF of 30 and above, including 35, 40, 45, etc.
  • Fillers [0439] According to the present invention, the compositions may further comprise at least one filler.
  • the term "filler” means any particle that is solid at room temperature and atmospheric pressure, used alone or in combination, which does not react chemically with the various ingredients of the emulsion and which is insoluble in these ingredients, even when these ingredients are raised to a temperature above room temperature and in particular to their softening point or their melting point.
  • the at least one filler has a melting point at least greater than 1700°C, for example, greater than 2000°C.
  • the at least one filler may have an apparent diameter ranging from 0.01 ⁇ m to 150 ⁇ m, such as from 0.5 ⁇ m to 120 ⁇ m, for example from 1 ⁇ m to 80 ⁇ m.
  • an apparent diameter corresponds to the diameter of the circle into which the elementary particle fits along its shortest dimension (thickness for leaflets).
  • the at least one filler may be absorbent, i.e., capable in particular of absorbing the oils of the composition and also the biological substances secreted by the skin, may be surface-treated, e.g., to make it lipophilic, and/or may be porous so as to absorb the sweat and/or sebum secreted by the skin.
  • the at least one filler may be chosen from inorganic and organic fillers, and may have any shape such as lamellar, spherical and/or oblong.
  • Non-limiting examples of the at least one inert filler include talc, mica, silica, kaolin, polyamide powders (such as Nylon® powder, and such as the product sold by Atochem as Orgasol®), poly- ⁇ -alanine powders, polyethylene powders, acrylic polymer powders (such as polymethyl- methacrylate (PMMA) powder, for instance the product sold by Wacker as Covabead LH-85 (particle size 10-12 ⁇ m) and the acrylic acid copolymer powder sold by Dow Corning as Polytrap®), polytetrafluoroethylene (Teflon®) powders, lauroyllysine, boron nitride, silica, kaolin, starch, starch derivatives, hollow polymer microspheres (such as those hollow polymer microspheres formed from polyvinylidene chloride and acrylonitrile, for instance the product sold by Nobel Industrie as Expancel®), and polymerized silicone microspheres (such as those poly
  • the composition according to the invention can be in the form of a tinted or non tinted dermatological composition or a care composition for keratin materials such as the skin, the lips and/or superficial body growths, in the form of an antisun composition or make-up-removing product in stick form. It can be used in particular as a care base for the skin, superficial body growths or the lips (lip balms, for protecting the lips against cold and/or sunlight and/or the wind, or care cream for the skin, the nails or the hair).
  • a deodorant product is personal hygiene product and does not relate to care, make-up or treatment of keratin materials, including keratinous fibers.
  • composition of the invention may also be in the form of a colored make-up product for the skin, in particular a foundation, optionally having care or treating properties, a blusher, a face powder, an eye shadow, a concealer product, an eyeliner, a make-up product for the body; a makeup product for the lips such as a lipstick, optionally having care or treating properties; a make-up product for superficial body growths such as the nails or the eyelashes, in particular in the form of a mascara cake, or for the eyebrows and the hair, in particular in the form of a pencil.
  • a colored make-up product for the skin in particular a foundation, optionally having care or treating properties, a blusher, a face powder, an eye shadow, a concealer product, an eyeliner, a make-up product for the body
  • a makeup product for the lips such as a lipstick, optionally having care or treating properties
  • a make-up product for superficial body growths such as the nails or the eyelashes, in particular in the form of a
  • the composition of the invention should be cosmetically or dermatologically acceptable, i.e., it should contain a non- toxic physiologically acceptable medium and should be able to be applied to the skin, superficial body growths or the lips of human beings.
  • the expression "cosmetically acceptable” means a composition of pleasant appearance, odor, feel and/or taste.
  • compositions of the present invention are provided.
  • methods of enhancing the appearance of keratinous material by applying compositions of the present invention to the keratinous material in an amount sufficient to enhance the appearance of the keratinous material are provided.
  • compositions of the present invention comprising at least one polyorganosiloxane containing polymer, preferably a polysilicone- polyamide copolymer, are applied topically to the desired area of the skin in an amount sufficient to treat, care for and/or make up the keratinous material, to cover or hide defects associated with keratinous material, skin imperfections or discolorations, or to enhance the appearance of keratinous material.
  • the compositions may be applied to the desired area as needed, preferably once or twice daily, more preferably once daily and then preferably allowed to dry before subjecting to contact such as with clothing or other objects.
  • the composition is preferably applied to the desired area that is dry or has been dried prior to application.
  • the composition further comprises at least one film forming agent,, at least one volatile oil, or a mixture thereof and/or pigments.
  • compositions having improved cosmetic properties such as, for example, improved long wear, transfer resistance or waterproof properties are provided.
  • the improved properties may also be chosen from improved flexibility, wearability, drying time or retention as well as reduced tackiness or migration over time.
  • the present invention also envisages kits and/or prepackaged materials suitable for consumer use containing one or more compositions according to the description herein.
  • the packaging and application device for any subject of the invention may be chosen and manufactured by persons skilled in the art on the basis of their general knowledge, and adapted according to the nature of the composition to be packaged.
  • the type of device to be used can be in particular linked to the consistency of the composition, in particular to its viscosity; it can also depend on the nature of the constituents present in the composition, such as the presence of volatile compounds.
  • all numbers expressing quantities of ingredients, reaction conditions, and so forth used in the specification and claims are to be understood as being modified in all instances by the term "about.” Accordingly, unless indicated to the contrary, the numerical parameters set forth in the following specification and attached claims are approximations that may vary depending upon the desired properties sought to be obtained by the present invention. [0451] Notwithstanding that the numerical ranges and parameters setting forth the broad scope of the invention are approximations, the numerical values set forth in the specific examples are reported as precisely as possible. Any numerical value, however, inherently contain certain errors necessarily resulting from the standard deviation found in their respective measurements. The following examples are intended to illustrate the invention without limiting the scope as a result. The percentages are given on a weight basis.
  • Preparation procedure 1. Heat A1 at 85 to 90°C for 15 minutes or until DC2-8179 is dissolved. Cool to room temperature. 2. Mix phase A ingredients, grinding with Silverson at 6000 to 7000 rpm for 30 to 40 minutes. 3. Add phase B1 ingredients, one at a time, mix well with Silverson at about 6000 rpm. 4. Add Butylparaben and Disteardimonium Hectorite, mixing with Silverson at 6000 rpm until good dispersion is obtained, then add propylene carbonate, mix at 6000 to 7000 rpm for 10 to 15 minutes. 5. Removed the main beaker from Silverson and transfer to Homogenizer. Warm the contents to 25 to 30°C. 6.
  • Preparation procedure 1. Heat A1 at 85 to 90°C for 15 minutes or until DC2-8179 is dissolved. Cool to room temperature. 2. Mix phase A ingredients, grinding with Silverson at 6000 to 7000 rpm for 30 to 40 minutes. 3. Add phase B1 ingredients, one at a time, mix well with Silverson at about 6000 rpm. 4. Add Butylparaben and Disteardimonium Hectorite, mixing with Silverson at 6000 rpm until good dispersion is obtained, then add propylene carbonate, mix at 6000 to 7000 rpm for 10 to 15 minutes. 5. Removed the main beaker from Silverson and transfer to Homogenizer. Warm the contents to 25 to 30°C. 6.
  • phase C In separate beaker, heat phase C to 40 to 45 °C. After it is uniform, cool to 25 to 30°C. 7. Add phase C slowly to the main beaker at 25 to 30°C to form an emulsion. Homogenize at 30% for 5 minutes.

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Abstract

L'invention concerne une composition acceptable sur le plan physiologique, notamment une composition cosmétique, exempte d'huile de silicones, qui comprend au moins un polymère contenant un polyorganosiloxane, comprenant au moins une fraction qui comprend : au moins un groupe polyorganosiloxane constitué de 1 à environ 1000 unités d'organosiloxane dans la chaîne de la fraction ou sous la forme d'un greffage et au moins deux groupes capables d'établir des interactions d'hydrogène.
PCT/US2003/039502 2003-12-12 2003-12-12 Composition cosmetique contenant un polymere polyorganosiloxane WO2005060922A1 (fr)

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AU2003297905A AU2003297905A1 (en) 2003-12-12 2003-12-12 Cosmetic composition containing a polyorganosiloxane polymer

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FR2895672A1 (fr) * 2006-01-03 2007-07-06 Oreal Composition cosmetique comprenant une huile
FR2902006A1 (fr) * 2006-06-13 2007-12-14 Oreal Composition cosmetique pour les levres associant un tensioactif phosphate et un polymere silicone
EP1938864A1 (fr) * 2006-12-29 2008-07-02 L'oreal Composition contenant un polymère polyorganosiloxane, agent épaississante et au moins un alcool volatile
FR2922104A1 (fr) * 2007-10-11 2009-04-17 Oreal Composition cosmetique structuree
WO2009053635A1 (fr) * 2007-10-11 2009-04-30 L'oreal Composition cosmetique structuree
US7601179B2 (en) * 2007-09-14 2009-10-13 L'oreal S.A. Methods of preserving artificial coloring on keratin materials
US7611544B2 (en) * 2007-09-14 2009-11-03 L'oreal S.A. Methods of artificially coloring hair
US7799093B2 (en) 2006-10-25 2010-09-21 L'ORéAL S.A. Coloring composition of keratinous fibers comprising at least one polysiloxane/polyurea block copolymer
AU2011213717B1 (en) * 2011-08-17 2011-12-08 Elc Management Llc Compositions and methods for tinting keratin material
EP1800650B2 (fr) † 2005-12-21 2013-08-14 L'Oréal Composition cosmétique à effet volumateur
WO2016030420A1 (fr) * 2014-08-28 2016-03-03 L'oreal Compositions comprenant un tensioactif de silicone, une poudre élastomère de silicone et une argile organo-modifiée
WO2016030838A1 (fr) * 2014-08-28 2016-03-03 L'oreal Gel-gel comprenant au moins deux charges avec un effet de flou
FR3025095A1 (fr) * 2014-08-28 2016-03-04 Oreal Composition gel/gel comprenant un filtre uv et un elastomere d'organopolysiloxane
WO2016096627A1 (fr) * 2014-12-18 2016-06-23 L'oreal Composition comprenant des particules de polymère, une huile à base d'hydrocarbure et une résine de silicone, et procédé l'employant
WO2019232151A1 (fr) * 2018-05-30 2019-12-05 Dow Silicones Corporation Émulsion et procédé pour la préparer
US11096871B2 (en) 2017-09-18 2021-08-24 Conopco, Inc. Personal care composition comprising a coated porous particle and dimethicone/vinyltrimethylsiloxysilicate and whitening agent
CN114015056A (zh) * 2021-10-13 2022-02-08 佛山市顺德区永创翔亿电子材料有限公司 一种耐电压耐电解液共聚物、极耳胶黏剂及极耳胶带
US11808833B2 (en) 2016-10-28 2023-11-07 Ppg Industries Ohio, Inc. Coatings for increasing near-infrared detection distances
US11809933B2 (en) 2018-11-13 2023-11-07 Ppg Industries Ohio, Inc. Method of detecting a concealed pattern
US12001034B2 (en) 2019-01-07 2024-06-04 Ppg Industries Ohio, Inc. Near infrared control coating, articles formed therefrom, and methods of making the same

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EP1800650B2 (fr) † 2005-12-21 2013-08-14 L'Oréal Composition cosmétique à effet volumateur
FR2895672A1 (fr) * 2006-01-03 2007-07-06 Oreal Composition cosmetique comprenant une huile
FR2902006A1 (fr) * 2006-06-13 2007-12-14 Oreal Composition cosmetique pour les levres associant un tensioactif phosphate et un polymere silicone
EP1870088A2 (fr) * 2006-06-13 2007-12-26 L'oreal Composition cosmétique pour les lèvres associant un tensioactif phosphaté et un polymère siliconé
EP1870088A3 (fr) * 2006-06-13 2008-03-19 L'oreal Composition cosmétique pour les lèvres associant un tensioactif phosphaté et un polymère siliconé
US7799093B2 (en) 2006-10-25 2010-09-21 L'ORéAL S.A. Coloring composition of keratinous fibers comprising at least one polysiloxane/polyurea block copolymer
EP1938864A1 (fr) * 2006-12-29 2008-07-02 L'oreal Composition contenant un polymère polyorganosiloxane, agent épaississante et au moins un alcool volatile
US7601179B2 (en) * 2007-09-14 2009-10-13 L'oreal S.A. Methods of preserving artificial coloring on keratin materials
US7611544B2 (en) * 2007-09-14 2009-11-03 L'oreal S.A. Methods of artificially coloring hair
WO2009053635A1 (fr) * 2007-10-11 2009-04-30 L'oreal Composition cosmetique structuree
FR2922104A1 (fr) * 2007-10-11 2009-04-17 Oreal Composition cosmetique structuree
AU2011213717B1 (en) * 2011-08-17 2011-12-08 Elc Management Llc Compositions and methods for tinting keratin material
US8491921B2 (en) 2011-08-17 2013-07-23 Elc Management, Llc Compositions and methods for tinting keratin material
US9028849B2 (en) 2011-08-17 2015-05-12 Elc Management Llc Compositions and methods for tinting keratin material
FR3025097A1 (fr) * 2014-08-28 2016-03-04 Oreal Gel/gel comprenant au moins deux charges a effet flouteur
US10813854B2 (en) 2014-08-28 2020-10-27 L'oreal Compositions comprising a silicone surfactant, a silicone elastomer powder and an organo-modified clay
WO2016030420A1 (fr) * 2014-08-28 2016-03-03 L'oreal Compositions comprenant un tensioactif de silicone, une poudre élastomère de silicone et une argile organo-modifiée
FR3025095A1 (fr) * 2014-08-28 2016-03-04 Oreal Composition gel/gel comprenant un filtre uv et un elastomere d'organopolysiloxane
FR3025102A1 (fr) * 2014-08-28 2016-03-04 Oreal Compositions comprenant un tensioactif silicone, une poudre d'elastomere de silicone et une argile organo-modifiee
KR20170031248A (ko) * 2014-08-28 2017-03-20 로레알 실리콘 계면활성제, 실리콘 엘라스토머 분말 및 유기-변형된 클레이를 포함하는 조성물
JP2017529337A (ja) * 2014-08-28 2017-10-05 ロレアル シリコーン界面活性剤、シリコーンエラストマー粉末、及びオルガノ修飾クレイを含む組成物
KR102020924B1 (ko) 2014-08-28 2019-09-11 로레알 실리콘 계면활성제, 실리콘 엘라스토머 분말 및 유기-변형된 클레이를 포함하는 조성물
WO2016030838A1 (fr) * 2014-08-28 2016-03-03 L'oreal Gel-gel comprenant au moins deux charges avec un effet de flou
WO2016096627A1 (fr) * 2014-12-18 2016-06-23 L'oreal Composition comprenant des particules de polymère, une huile à base d'hydrocarbure et une résine de silicone, et procédé l'employant
FR3030263A1 (fr) * 2014-12-18 2016-06-24 Oreal Composition comprenant des particules polymeres, une huile hydrocarbonee et une resine siliconee, et procede la mettant en oeuvre
US10219991B2 (en) 2014-12-18 2019-03-05 L'oreal Composition comprising polymer particles, a hydrocarbon-based oil and a silicone resin, and process using the same
US11808833B2 (en) 2016-10-28 2023-11-07 Ppg Industries Ohio, Inc. Coatings for increasing near-infrared detection distances
US11977154B2 (en) 2016-10-28 2024-05-07 Ppg Industries Ohio, Inc. Coatings for increasing near-infrared detection distances
US11096871B2 (en) 2017-09-18 2021-08-24 Conopco, Inc. Personal care composition comprising a coated porous particle and dimethicone/vinyltrimethylsiloxysilicate and whitening agent
WO2019232151A1 (fr) * 2018-05-30 2019-12-05 Dow Silicones Corporation Émulsion et procédé pour la préparer
US11809933B2 (en) 2018-11-13 2023-11-07 Ppg Industries Ohio, Inc. Method of detecting a concealed pattern
US12050950B2 (en) 2018-11-13 2024-07-30 Ppg Industries Ohio, Inc. Method of detecting a concealed pattern
US12001034B2 (en) 2019-01-07 2024-06-04 Ppg Industries Ohio, Inc. Near infrared control coating, articles formed therefrom, and methods of making the same
CN114015056A (zh) * 2021-10-13 2022-02-08 佛山市顺德区永创翔亿电子材料有限公司 一种耐电压耐电解液共聚物、极耳胶黏剂及极耳胶带
CN114015056B (zh) * 2021-10-13 2023-02-21 佛山市顺德区永创翔亿电子材料有限公司 一种耐电压耐电解液共聚物、极耳胶黏剂及极耳胶带

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