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WO1997021423A1 - Composition topique de retinoide - Google Patents

Composition topique de retinoide Download PDF

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Publication number
WO1997021423A1
WO1997021423A1 PCT/US1996/019302 US9619302W WO9721423A1 WO 1997021423 A1 WO1997021423 A1 WO 1997021423A1 US 9619302 W US9619302 W US 9619302W WO 9721423 A1 WO9721423 A1 WO 9721423A1
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WO
WIPO (PCT)
Prior art keywords
composition
weight
oil
silicone
phase
Prior art date
Application number
PCT/US1996/019302
Other languages
English (en)
Inventor
Larry Richard Robinson
Brent William Mason
Greg George Hillebrand
Joseph Michael Zukowski
Original Assignee
The Procter & Gamble Company
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by The Procter & Gamble Company filed Critical The Procter & Gamble Company
Priority to AU11289/97A priority Critical patent/AU1128997A/en
Publication of WO1997021423A1 publication Critical patent/WO1997021423A1/fr

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/67—Vitamins
    • A61K8/671—Vitamin A; Derivatives thereof, e.g. ester of vitamin A acid, ester of retinol, retinol, retinal
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/04—Dispersions; Emulsions
    • A61K8/06—Emulsions
    • A61K8/064—Water-in-oil emulsions, e.g. Water-in-silicone emulsions
    • 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
    • A61K8/58—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing atoms other than carbon, hydrogen, halogen, oxygen, nitrogen, sulfur or phosphorus
    • A61K8/585—Organosilicon compounds
    • 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
    • A61Q19/00—Preparations for care of the skin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
    • A61Q17/04—Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/08—Anti-ageing preparations

Definitions

  • the present invention relates to topical retinoid compositions in the form of water-in-silicone emulsions that provide improved oxidative stability for the retinoid therein.
  • retinoid compositions are known for topical use on human skin. These topical retinoids can improve the texture or appearance of skin, especially aged or wrinkled skin, or skin that has been excessively exposed to ultraviolet radiation, wind, low humidity, harsh surfactants, abrasives, and the like.
  • Retinoids most commonly described for this purpose include retinol, retinal, retinoic acid, and retinyl esters, which can be incorporated into and applied as aqueous gels, anhydrous ointments or creams, water-in- oil emulsions or oil-in-water emulsions.
  • Water-in-oil emulsions are especially useful vehicles for moisturizing and delivering active materials such as retinoids to the skin.
  • the discontinuous water phase provides moisture to the skin under an occlusive oil layer provided by the continuous oil phase of the emulsion.
  • the oil soluble retinoids are typically contained in the oil phase, and after topical application, diffuse through the applied oil layer to the surface of the skin.
  • many of these water-in-oil emulsion compositions are oxidatively unstable, due primarily to trace contaminants in the water and oil materials used in formulating the emulsion, and cannot be stored for more than a brief period of time without undesirable oxidation of the retinoid.
  • Retinol is especially susceptible to oxidation in these water-in-oil emulsion systems.
  • Water-in-silicone emulsions are especially useful in providing a means for topically delivering active materials to the skin.
  • These silicone-based emulsions normally provide easier spreadability, lower occlusion, and contain higher water concentrations for skin moisturization than comparable non-silicone based water-in-oil emulsions.
  • the oxygen permeability of the silicone oil in these emulsions is normally greater than for most nonsilicone oils, thus reducing oxidative stability of any oxidative- sensitive materials therein.
  • One attempt at improving the oxidative stability of retinoid-containing water-in-oil emulsions involves the use of antioxidants in combination with the retinoid.
  • antioxidants are especially useful when used in combination with highly oxidation-sensitive retinoids such as retinol. Although antioxidants would seem to improve oxidative stability of certain retinoids in these emulsion systems, and even permit the use of retinol in a water-in-silicone emulsion system, these added materials can increase raw material costs and introduce additional chemical and physical compatibility issues.
  • select water-in-silicone emulsion systems can be formulated to provide an oxidatively stable vehicle for topical retinoids.
  • the select emulsion systems comprise a discontinuous aqueous phase dispersed in a continuous silicone phase, wherein the continuous silicone phase comprises between about 50% and about 99.9% by weight of organopolysiloxane oil and less than about 50% by weight of a non-silicone oil.
  • the polyorganosiloxane oil component when incorporated into the water-in-silicone emulsion system described herein, provides topical retinoids with more oxidative stability over extended periods of time than comparable water-in-oil emulsions containing lower concentrations of the polyorganosiloxane oil. This finding was especially unexpected in view of the prior art which teaches that silicone oils have higher oxygen permeabilities than other non-silicone oils, and that higher oxygen permeabilities will enhance rather than reduce oxidative processes therein.
  • the present invention is directed to topical compositions comprising (a) from about 1% to about 60% of a continuous silicone phase by weight of the composition, wherein the continuous silicone phase comprises (i) from about 50% to about 99.9% organopolysiloxane and less than about 50% by weight of a nonsilicone oil, by weight of the continuous silicone phase; (b) from a6out 30% to about 90% of an aqueous discontinuous phase by weight of the composition; (c) from about 0.0001 % to about 5% retinoid by weight of the composition; and (d) from about 0.1% to about 10% of an emulsifier by weight of the composition.
  • the topical compositions provide improved oxidative stability for retinoids in water-in-silicone emulsions, and are preferably substantially free of added antioxidant materials.
  • the present invention is also directed to methods of using the topical compositions on human skin.
  • compositions of the present invention are water-in-silicone emulsions which comprise a discontinuous aqueous phase, a continuous silicone phase, a retinoid dispersed or dissolved in the continuous silicone phase, and an emulsifier.
  • a discontinuous aqueous phase a continuous silicone phase
  • a retinoid dispersed or dissolved in the continuous silicone phase a retinoid dispersed or dissolved in the continuous silicone phase
  • an emulsifier an emulsifier.
  • compositions of the present invention are useful for topical application on human skin to deliver a safe and effective amount of a retinoid to the skin.
  • safe and effective refers to an amount of retinoid in the composition that when topically applied will improve the appearance and/or texture of human skin, but will avoid serious side effects, e.g, to provide a reasonable benefit to risk ratio within the scope of sound medical judgment.
  • topical retinoids can help minimize or eliminate the development of wrinkles, including both fine superficial wrinkles and coarse deep wrinkles, skin lines, sagging, discoloration, age spots, keratoses, hyperkeratinization, elastosis, collagen breakdown, and/or other histological changes in the stratum corneum, dermis, epidermis, the vascular system, and underlying tissues.
  • compositions of the present invention are stable over an extended period of time, especially when packaged and stored for periods of time exceeding about sixty days.
  • stable refers to improved oxidative stability of the dispersed retinoid in the continuous silicone phase of the composition.
  • the compositions may be packaged and stored as commercial product for extended periods, even though such compositions may be substantially free of antioxidants.
  • compositions of the present invention can comprise, consist of, or consist essentially of, the essential as well as optional ingredients, components, or limitations described in detail hereinafter.
  • the continuous silicone phase of the compositions of the present invention comprise a safe and effective amount of a retinoid, preferably at concentrations of from about 0.0001% to about 5%, preferably from about 0.01% to about 2%, more preferably from about 0.01% to about 1%, by weight of the compositions.
  • Suitable retinoids include retinol, synthetic or natural analogs of retinol, and geometric and stereoisomers of such compounds.
  • Preferred retinoids include retinol, retinoic acid, retinal and retinyl esters such as retinyl acetate, retinyl butyrate, retinyl propionate, retinyl octanoate, retinyl laurate, retinyl palmitate, retinyl oleate and retinyl linoleate.
  • Most preferred are those retinoids that are highly suseptable to oxidation in a water-in-oil emulsion, e.g., retinol.
  • compositions of the present invention comprise from about 1% to about 60%, preferably from about 5% to about 40%, more preferably from about 10% to about 20%, by weight of a continuous silicone phase, wherein the continuous silicone phase comprises at least about 50%, preferably from about 60% to about 99.9%, more preferably from about 70% to about 99.9%, and even more preferably from about 80% to about 99.9%, polyorganosiloxane oil by weight of the continuous silicone phase.
  • the continuous oil phase of the composition herein may comprise up to about 50% non-silicone oils, preferably less about 40%, more preferably less than about 30%, even more preferably less than about 10%, and most preferably less than about 2%, by weight of the continuous silicone phase. Concentrations of non-silicone oils in the continuous silicone phase are minimized so as to further enhance oxidative stability of the selected retinoid in the compositions. It has been found that retinoids, especially retinol, are less susceptible to oxidation when incorporated into water-in-oil systems containing at least 50% by weight of organopolysiloxane oil, than in comparable systems containing lower or no concentrations of organopolysiloxane oil..
  • the organopolysiloxane oil for use in the composition may be volatile, non-volatile, or a mixture of volatile and non-volatile silicones.
  • nonvolatile refers to those silicones that are liquid under ambient conditions and have a flash point (under one atmospheric of pressure) of at greater than about 100°C.
  • volatile refers to all other silicone oils.
  • continuous silicone phase refers to the continuous oil phase of the composition, which oil phase comprises at least about 50% by weight of polyorganosiloxane oil, and exists as an external phase that contains or surrounds the discontinuous aqueous phase described hereinafter.
  • oil phase comprises at least about 50% by weight of polyorganosiloxane oil, and exists as an external phase that contains or surrounds the discontinuous aqueous phase described hereinafter.
  • oil referred to herein has a melting point of about 25°C or less under about one atmosphere of pressure.
  • Suitable organopolysiloxanes can be selected from a wide variety of silicones spanning a broad range of volatilities and viscosities.
  • suitable organopolysiloxane oils include polyalkylsiloxanes, cyclic polyalkylsiloxanes, and polyalkylarylsiloxanes.
  • Polyalkylsiloxanes useful in the composition herein include polyalkylsiloxanes with viscosities of from about 0.5 to about 1 ,000,000 centistokes at 25 ⁇ C.
  • Such polyalkylsiloxanes can be represented by the general chemical formula R3SiO[R2SiO] x SiR3 wherein R is an alkyl group having from one to about 30 carbon atoms (preferably R is methyl or ethyl, more preferably methyl; also mixed alkyl groups can be used in the same molecule), and x is an integer from 0 to about 10,000, chosen to achieve the desired molecular weight which can range to over about 10,000,000.
  • Commercially available polyalkylsiloxanes include the polydimethylsiloxanes, which are also known as dimethicones, examples of which include the Vicasil® series sold by General Electric Company and the Dow Corning® 200 series sold by Dow Corning Co ⁇ oration.
  • Suitable polydimethylsiloxanes include Dow Corning® 200 fluid having a viscosity of 0.65 centistokes and a boiling point of 100°C, Dow Corning® 225 fluid having a viscosity of 10 centistokes and a boiling point greater than 200 ⁇ C, and Dow Corning® 200 fluids having viscosities of 50, 350, and 12,500 centistokes, respectively, and boiling points greater than 200°C.
  • Suitable dimethicones include those represented by the chemical formula
  • R is straight or branched chain alkyl having from two to about 30 carbon atoms and x and y are each integers of 1 or greater selected to achieve the desired molecular weight which can range to over about 10,000,000.
  • alkyl- substituted dimethicones include cetyl dimethicone and lauryl dimethicone.
  • Cyclic polyalkylsiloxanes suitable for use in the composition include those represented by the chemical formula [SiR2-O] n wherein R is an alkyl group (preferably R is methyl or ethyl, more preferably methyl) and n is an integer from about 3 to about 8, more preferably n is an integer from about 3 to about 7, and most preferably n is an integer from about 4 to about 6.
  • R is an alkyl group
  • n is an integer from about 3 to about 8
  • preferably n is an integer from about 3 to about 7
  • most preferably n is an integer from about 4 to about 6.
  • R is methyl
  • these materials are typically referred to as cyclomethicones.
  • Commercially available cyclomethicones include Dow Corning® 244 fluid having a viscosity of 2.5 centistokes, and a boiling point of 172°C, which primarily contains the cyclomethicone tetramer (i.e.
  • Dow Corning® 245 fluid having a viscosity of 4.2 centistokes and a boiling point of 205°C, which primarily contains a mixture of the cyclomethicone tetramer and pentamer (i.e.
  • n 4 and 5
  • materials such as trimethylsiloxysilicate, which is a polymeric material corresponding to the general chemical formula [(CH2)3SiO ⁇ /2] ⁇ [Si ⁇ 2ly, wherein x is an integer from about 1 to about 500 and y is an integer from about 1 to about 500.
  • a commercially available trimethylsiloxysilicate is sold as a mixture with dimethicone as Dow Corning® 593 fluid.
  • Dimethiconols are also suitable for use in the composition. These compounds can be represented by the chemical formulas R3SiO[R2SiO] x SiR2 ⁇ H and HOR2SiO[R2SiO] x SiR2OH wherein R is an alkyl group (preferably R is methyl or ethyl, more preferably methyl) and x is an integer from 0 to about 500, chosen to achieve the desired molecular weight.
  • Commercially available dimethiconols are typically sold as mixtures with dimethicone or cyclomethicone (e.g. Dow Corning® 1401 , 1402, and 1403 fluids).
  • Polyalkylaryl siloxanes are also suitable for use in the composition.
  • Polymethylphenyl siloxanes having viscosities from about 15 to about 65 centistokes at 25 ⁇ C are especially useful.
  • the continuous silicone phase comprises less than about 50% by weight of a non-silicone oil by weight of the continuous silicone phase, and preferably the concentration of such non-silicone oils is minimized or avoided altogether in formulating the continuous silicone oil phase of the compositions herein.
  • non-silicone oils suitable for use in the continuous silicone phase are well known in the chemical arts in topical personal care products in the form of water-in-oil emulsions, e.g., mineral oil, vegetable oils, synthetic oils, semisynthetic oils, etc.
  • the topical compositions of the present invention comprise from about 30% to about 90%, more preferably from about 50% to about 85%, and most preferably from about 70% to about 80% of a discontinuous aqueous phase.
  • the discontinuous aqueous phase is a dispersion of small aqueous particles or droplets suspended in and surrounded by the continuous silicone phase described hereinbefore.
  • the discontinuous aqueous phase can be water, or a combination of water and one or more water soluble or dispersible ingredients.
  • option ingredients include thickeners, acids, bases, salts, chelants, gums, water-soluble or dispersible alcohols and polyols, buffers, preservatives, sunscreening agents, colorings, and the like.
  • compositions of the present invention will typically comprise from about 25% to about 90%, preferably from about 40% to about 80%, more preferably from about 60% to about 80%, water in the discontinuous aqueous phase by weight of the composition.
  • compositions of the present invention comprise from about 0.1% to about 10%, preferably from about 0.5% to about 7.5%, more preferably from about 1% to about 5% , emulsifier by weight of the composition.
  • the emulsifier helps disperse and suspend the discontinuous aqueous phase within the continuous silicone phase of the composition.
  • emulsifying agents can be used in the composition, provided that the selected emulsifying agent is chemically and physically compatible with essential components of the composition, and provides the desired dispersion characteristics.
  • Suitable emulsifiers include silicone emulsifiers, non-silicon-containing emulsifiers, and mixtures thereof, known by those skilled in the art for use in topical personal care products.
  • these emulsifiers Preferably these emulsifiers have an HLB value of less than about 14, more preferably from about 2 to about 14, and most preferably from about 4 to about 14.
  • Emulsifiers having an HLB value outside of these ranges can be used in combination with other emulsifiers to achieve an effective weighted average HLB for the combination that falls within the ranges described herein.
  • Silicone emulsifiers are preferred in the compositions herein. These emulsifiers are typically organically modified organopolysiloxanes, also known as silicone surfactants. Especially useful silicone emulsifiers include dimethicone copolyols, which are polydimethyl siloxanes which have been modified to include polyether side chains such as polyethylene oxide chains, polypropylene oxide chains, mixtures of these chains, and polyether chains containing moieties derived from both ethylene oxide and propylene oxide. Other examples include alkyl-modified dimethicone copolyols, i.e. compounds which contain pendent C2-C30 pendant side chains. Still other useful dimethicone copolyols include materials having various cationic, anionic, amphoteric, and zwiterionic pendant moieties.
  • Dimethicone copolyol emulsifiers useful in the composition herein are described, for example, in U.S. Patent No. 4,960,764; EP 330,369; G.H. Dahms, et al., "New Formulation Possibilities Offered by Silicone Copolyols," Cosmetics & Toiletries, vol. 110, pp. 91-100, March 1995; M.E. Carlotti et al., "Optimization of W/O-S Emulsions And Study Of The Quantitative Relationships Between Ester Structure And Emulsion Properties," J. Dispersion Science And Technology, 13(3), 315-336 (1992); P.
  • Suitable non-silicone emulsifiers include various non-ionic and anionic emulsifying agents such as sugar esters and polyesters, alkoxylated sugar esters and polyesters, C1-C30 fatty acid esters of C1-C30 fatty alcohols, alkoxylated derivatives of C1-C30 fatty acid esters of C1-C30 fatty alcohols, alkoxylated ethers of C1-C30 fatty alcohols, polyglyceryl esters of C1-C30 fatty acids, C1-C30 esters of polyols, C1-C30 ethers of polyols, alkyl phosphates, polyoxyalkylene fatty ether phosphates, fatty acid amides, acyl lactylates, soaps, and mixtures thereof.
  • non-ionic and anionic emulsifying agents such as sugar esters and polyesters, alkoxylated sugar esters and polyesters, C1-C30 fatty acid esters
  • emulsifiers are described, for example, in McCutcheon's, Detergents and Emulsifiers. North American Edition (1986), published by Allured Publishing Co ⁇ oration; U.S. Patent 5,011 ,681 ; U.S. Patent 4,421 ,769; and U.S. Patent 3,755,560, which descriptions are incorporated herein by reference.
  • the topical composition of the present invention may further comprise one or more optional components, provide that such optional components are chemically and physically compatible with the essential components of the composition, or do not unduly affect product performance.
  • the topical compositions are preferably substantially free of conventional antioxidants which are known for use in improving oxidative stability of susceptible materials in personal care products. Although it is understood that the topical compositions may optionally contain such conventional antioxidants. Examples of antioxidants include butylated hydroxytoluene, butylated hydroxyanisole, ascorbic acid, propyl gallate, and alpha tocopherol, and examples of chelants include ethylenediaminetetracetic acid (EDTA) and related materials.
  • EDTA ethylenediaminetetracetic acid
  • substantially fee refers to concentrations of antioxidant in the water-in-silicone compositions of the present invention that are too low to significantly improve oxidative stability of the selected retinoid in the compositions herein.
  • Optional materials include sunscreening agents, examples of which a described in U.S. Patent 5,087,445; U.S. Patent 5,073,372; U.S. Patent 5,073,371 ; and Segarin, et al., at Chapter VIII, pages 189 et seq., of Cosmetics Science and Technology, which descriptions are inco ⁇ orated herein by reference.
  • Other optional materials include sunless tanning agents, and skin bleaching or lightening agents.
  • optional materials include known or conventional humectant, moisturizing, or skin conditioning materials. Concentrations of such optional materials will generally range from about 0.1 % to about 20%, preferably from about 1 % to about 10%, most preferably from about 2% to about 5%, by weight of the composition. These materials include guanidine; glycolic acid and glycolate salts; lactic acid and lactate salts; aloe vera; polyhydroxy alcohols; polyethylene glycols; sugars and starches; sugar and starch derivatives; hyaluronic acid; lactamide monoethanolamine; acetamide monoethanolamine; propoxylated glycerols, C1-C30 monoesters and polyesters of sugars and related materials, and mixtures thereof.
  • optional materials include cosmetic and pharmaceutical ingredients commonly used in the skin care industry, examples of which include absorbents, abrasives, anti-acne agents, anticaking agents, antifoaming agents, antimicrobial agents, binders, biological additives, buffering agents, bulking agents, chemical additives, colorants, cosmetic astringents, cosmetic biocides, denaturants, drug astringents, external analgesics, film formers, fragrance components, humectants, opacifying agents, pH adjusters, plasticizers, preservatives, propellants, reducing agents, additional skin-conditioning agents, skin protectants, solvents, suspending agents (nonsurfactant), ultraviolet light absorbers, viscosity increasing agents (aqueous and nonaqueous) and solubilizing agents.
  • absorbents abrasives, anti-acne agents, anticaking agents, antifoaming agents, antimicrobial agents, binders, biological additives, buffering agents, bulking agents, chemical additive
  • composition of the present invention may further comprise additional materials known for use in topical compositions to improve the appearance and/or texture of aged or otherwise wrinkled skin.
  • additional materials include N-acetylcysteine, N-acetyl-L-cysteine, N- acetyl-D-cysteine, derivatives thereof and salts thereof, descriptions of which are set forth in U.S. Patent 5,296,500, which descriptions are inco ⁇ orated herein by reference.
  • Concentrations of N-acetylcysteine and related compounds will generally range from about 0.01% to about 50%, preferably from about 0.1% to about 10%, more preferabbly from about 0.25% to about 5%, by weight of the composition.
  • ком ⁇ онентs include aesthetic components such as fragrances, pigments, colorings, essential oils, skin sensates, astringents, skin soothing agents and skin healing agents.
  • compositions of the present invention may be applied topically to human skin to improve the appearance and/or texture of the skin, or to otherwise deliver topical retinoids to human skin.
  • the compositions of the present invention may be topically applied to human skin to help reduce, efface, and/or prevent wrinkles in human skin, to help moisturize skin, and to help treat histological changes associated with skin aging or excessive exposure to ultraviolet radiation, wind, low humidity, harsh surfactants, and/or abrasives.
  • Methods of using the composition comprise applying to the skin a safe and effective amount of the compositions of the present invention.
  • the amount of the retinoid in the composition and the frequency of application on the skin will vary widely depending upon the condition of the skin and the effect desired. Such methods will typically involve application of from about 0.1 mg/cm2 to about 10 mg/cm ⁇ (mg of the composition per area of skin).
  • EXAMPLE 1 The following describes a retinol-containing water-in-silicone emulsion of the present invention.
  • the composition is prepared by combining the following ingredients using conventional mixing techniques.
  • Vitamin A alcohol blend from Roche Vitamins and Fine Chemicals
  • a suitable vessel the methyl paraben, benzyl alcohol and ethanol are combined with mixing until a solution is obtained. Next, the water, glycerin, and tetrasodium EDTA are added with mixing.
  • Vitamin A alcohol , cyclomethicone, polyglyceryl-4 isostearate (and) cetyl dimethicone copolyol (and) hexyl laurate, and cyclomethicone (and) dimethicone copolyol are first combined and then added with mixing to form the emulsion. Next the fragrance is added with stirring.
  • the resulting water-in-silicone composition is useful for application of retinol to human skin, and to improving the appearance and texture of human skin.
  • the resulting composition provides oxidative stability for the retinol.
  • the following describes a retinoid-containing water-in-silicone emulsion of the present invention.
  • the retinoid is retinyl palmitate.
  • the composition is prepared by combining the following ingredients using conventional mixing techniques.
  • a suitable vessel the methyl paraben, benzyl alcohol and ethanol are combined with mixing until a solution is obtained. Next, the water, glycerin, and tetrasodium EDTA are added with mixing.
  • Vitamin A palmitate, cyclomethicone, polyglyceryl-4 isostearate (and) cetyl dimethicone copolyol (and) hexyl laurate, and cyclomethicone (and) dimethicone copolyol are first combined and then added with mixing to form the emulsion. Next the fragrance is added with stirring.
  • the resulting water-in-silicone composition is useful for application of a retinoid to human skin, and to improving the appearance and texture of human skin.
  • the resulting composition provides oxidative stability for the retinoid.

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Abstract

Compositions topiques de rétinol et procédés d'application de ces compositions sur la peau de patients humains. Les compositions topiques comprennent (a) entre environ 1 % et environ 60 % d'une phase silicone continue en poids de la composition, ladite phase silicone continue étant constituée d'environ 50 % à environ 99,9 % d'organopolysiloxane et de moins d'environ 50 % en poids d'une huile non silicone, en poids de la phase silicone continue; (b) entre environ 30 % et environ 90 % d'une phase discontinue aqueuse en poids de la composition; (c) entre environ 0,0001 % et environ 5 % de rétinoïde en poids de la composition; et (d) entre environ 0,1 % et environ 10 % d'un émulsifiant en poids de la composition. Ces compositions topiques confèrent une stabilité accrue à l'oxydation aux rétinoïdes incorporés dans des émulsions du type eau-en-huile, elles sont par ailleurs de préférence sensiblement dépouvues d'antioxydants classiques.
PCT/US1996/019302 1995-12-11 1996-12-04 Composition topique de retinoide WO1997021423A1 (fr)

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AU11289/97A AU1128997A (en) 1995-12-11 1996-12-04 Topical retinoid composition

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US57027595A 1995-12-11 1995-12-11
US08/570,275 1995-12-11

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Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1055720A3 (fr) * 1999-05-28 2001-03-07 JOHNSON & JOHNSON CONSUMER COMPANIES, INC. Compositions pour la stabilisation de composés sensibles à l'oxygène
DE10020447A1 (de) * 2000-03-31 2001-10-11 Henkel Kgaa Verwendung von Protease-Inhibitoren in der Kosmetik und Pharmazie
US6974799B2 (en) 2003-11-17 2005-12-13 Sederma S.A.S. Compositions containing mixtures of tetrapeptides and tripeptides
EP1704853A3 (fr) * 2005-03-24 2007-01-24 Neutrogena Corporation Composition d'émulsion du type eau-dans-silicone
US7235249B2 (en) 2002-03-28 2007-06-26 The Procter & Gamble Company Methods for regulating the condition of mammalian keratinous tissue via topical application of vitamin B6 compositions
EP2105123A2 (fr) 2001-03-22 2009-09-30 The Procter & Gamble Company Compositions de soins dermatologiques contenant une amine-sucre et un composé de vitamine B3
US8360973B2 (en) 2000-11-29 2013-01-29 L'oreal Process for acquiring scanned image data relating to an external body portion and/or a product applied thereto
US8871717B2 (en) 2005-04-27 2014-10-28 The Procter & Gamble Company Personal care compositions
WO2016003505A1 (fr) 2014-07-02 2016-01-07 Geoffrey Brooks Consultants, Llc Compositions à base de peptide et procédés d'utilisation
US9616011B2 (en) 2005-04-27 2017-04-11 The Procter & Gamble Company Personal care compositions
US9856290B2 (en) 2013-12-10 2018-01-02 Sussex Research Laboratories Inc. Glycopeptide compositions and uses thereof

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WO1986006275A1 (fr) * 1985-04-22 1986-11-06 Avon Products, Inc. Compositions et procede permettant de diminuer les rides
EP0330496A2 (fr) * 1988-02-25 1989-08-30 Beecham Group Plc Composition pour le traitement de la peau
EP0435483A2 (fr) * 1989-12-07 1991-07-03 Unilever Plc Composition cosmétique
EP0512814A1 (fr) * 1991-05-07 1992-11-11 Unilever Plc Composition cosmétique
WO1993000085A1 (fr) * 1991-06-27 1993-01-07 Johnson And Johnson Consumer Products, Inc. Compositions stabilisees de soin pour la peau, contenant des retinoides
FR2714595A1 (fr) * 1993-12-30 1995-07-07 Oreal Emulsion eau dans huile contenant du rétinol, son utilisation et son conditionnement.

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WO1986006275A1 (fr) * 1985-04-22 1986-11-06 Avon Products, Inc. Compositions et procede permettant de diminuer les rides
EP0330496A2 (fr) * 1988-02-25 1989-08-30 Beecham Group Plc Composition pour le traitement de la peau
EP0435483A2 (fr) * 1989-12-07 1991-07-03 Unilever Plc Composition cosmétique
EP0512814A1 (fr) * 1991-05-07 1992-11-11 Unilever Plc Composition cosmétique
WO1993000085A1 (fr) * 1991-06-27 1993-01-07 Johnson And Johnson Consumer Products, Inc. Compositions stabilisees de soin pour la peau, contenant des retinoides
FR2714595A1 (fr) * 1993-12-30 1995-07-07 Oreal Emulsion eau dans huile contenant du rétinol, son utilisation et son conditionnement.

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1055720A3 (fr) * 1999-05-28 2001-03-07 JOHNSON & JOHNSON CONSUMER COMPANIES, INC. Compositions pour la stabilisation de composés sensibles à l'oxygène
DE10020447A1 (de) * 2000-03-31 2001-10-11 Henkel Kgaa Verwendung von Protease-Inhibitoren in der Kosmetik und Pharmazie
US8360973B2 (en) 2000-11-29 2013-01-29 L'oreal Process for acquiring scanned image data relating to an external body portion and/or a product applied thereto
EP2105123A2 (fr) 2001-03-22 2009-09-30 The Procter & Gamble Company Compositions de soins dermatologiques contenant une amine-sucre et un composé de vitamine B3
US7235249B2 (en) 2002-03-28 2007-06-26 The Procter & Gamble Company Methods for regulating the condition of mammalian keratinous tissue via topical application of vitamin B6 compositions
US6974799B2 (en) 2003-11-17 2005-12-13 Sederma S.A.S. Compositions containing mixtures of tetrapeptides and tripeptides
EP1704853A3 (fr) * 2005-03-24 2007-01-24 Neutrogena Corporation Composition d'émulsion du type eau-dans-silicone
US8871717B2 (en) 2005-04-27 2014-10-28 The Procter & Gamble Company Personal care compositions
US9616011B2 (en) 2005-04-27 2017-04-11 The Procter & Gamble Company Personal care compositions
US10130577B2 (en) 2005-04-27 2018-11-20 The Procter & Gamble Company Personal care compositions
US9856290B2 (en) 2013-12-10 2018-01-02 Sussex Research Laboratories Inc. Glycopeptide compositions and uses thereof
WO2016003505A1 (fr) 2014-07-02 2016-01-07 Geoffrey Brooks Consultants, Llc Compositions à base de peptide et procédés d'utilisation

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