WO1992017159A2 - Compositions emulsionnees stabilisees destinees a donner a leur peau humaine un hale artificiel - Google Patents

Compositions emulsionnees stabilisees destinees a donner a leur peau humaine un hale artificiel Download PDF

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Publication number
WO1992017159A2
WO1992017159A2 PCT/US1992/001980 US9201980W WO9217159A2 WO 1992017159 A2 WO1992017159 A2 WO 1992017159A2 US 9201980 W US9201980 W US 9201980W WO 9217159 A2 WO9217159 A2 WO 9217159A2
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Prior art keywords
ethylhexyl
emulsion composition
composition according
acid ester
skin
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PCT/US1992/001980
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English (en)
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WO1992017159A3 (fr
Inventor
Frederik Winfield Woodin, Jr.
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Richardson-Vicks Inc.
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Publication of WO1992017159A2 publication Critical patent/WO1992017159A2/fr
Publication of WO1992017159A3 publication Critical patent/WO1992017159A3/fr

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Classifications

    • 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
    • A61Q19/04—Preparations for care of the skin for chemically tanning the skin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/35—Ketones, e.g. benzophenone
    • 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
    • A61K8/55—Phosphorus 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
    • A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • A61K8/8141—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • A61K8/8147—Homopolymers or copolymers of acids; Metal or ammonium salts thereof, e.g. crotonic acid, (meth)acrylic acid; Compositions of derivatives of such polymers

Definitions

  • the present invention relates to emulsion compositions having improved stability which are useful for imparting an artificial tan to human skin.
  • These emulsions contain dihydroxyacetone, at least one alkyl phosphate, and at least one carboxylic acid copolymer in which the ratio of alkyl phosphate to carboxylic acid copolymer is from about 5:1 to about 1:5.
  • these emulsion compositions contain one or more sunscreens, and are also useful for protecting human skin from the harmful effects of sunlight and other sources of ultraviolet radiation.
  • the present invention also relates to methods for preparing these compositions, methods for providing an artificial tan to human skin, and methods for protecting human skin from the harmful effects of ultraviolet radiation.
  • Dihydroxyacetone is relatively sensitive to heat, light, moisture, and alkaline pH. Dihydroxyacetone can react with other ingredients in a formulation, especially with nitrogen-containing compounds, such as amines, amino
  • d hydroxyacetone is believed to provide an artificial tan to human skin by its reaction with the nitrogen containing proteins of the skin. See L. Goldman et al., "Investigative Studies with the Skin Coloring Agents Dihyroxyacetone and Glyoxal", The Journal of Investigative Dermatology, vol. 35, pp. 161-164 (1960); and E. Wittgenstein et al., "Reaction of Dihydroxyacetone (DHA) with Human Skin Callus and Amino Compounds", The Journal of Investigative Dermatology, vol. 36, pp. 283-286 (1961).
  • a sun-tanned appearance is a symbol of a healthy, dynamic, and active life. Yet, the damaging effects of sunlight and artificial sources of ultraviolet radiation on the skin are well documented. Furthermore these effects are cumulative and potentially serious. These effects include erythema (i.e. sunburn), skin cancer, and premature aging of the skin. These adverse effects associated with exposure to ultraviolet radiation are more fully discussed in DeSimone, "Sunscreen and Suntan Products", Handbook of Nonprescription Drugs, 7th Ed., Chapter 26, pp. 499-511 (American Pharmaceutical Association, Washington, D.C.; 1982); Grove and Forbes, "A Method for Evaluating the Photoprotection Action of Sunscreen Agents against UV-A Radiation", International Journal of Cosmetic Science. 4, pp. 15-24 (1982); and U.S. Patent 4,387,089, DePolo, issued June 7, 1983; the disclosures of all of which are incorporated herein by reference.
  • Sunscreens are the most common agents used for sun protection. However, sunscreens also have the disadvantage of preventing or greatly diminishing the cosmetically desirable tanning response. Thus, if an individual uses a sunscreen for protection from ultraviolet radiation, he or she is forced to forego a tanned appearance. Therefore, it would be highly desirable to provide protection from the harmful effects of ultraviolet radiation, and yet at the same time deliver a tanned appearance to the skin.
  • the present invention relates to an artificial tanning oil-in-water emulsion composition having improved stability, comprising:
  • compositions of the instant invention are in the form of oil-in-water emulsions whereby the oil phase can contain typical oil-soluble components and the water phase can contain typical water-soluble materials.
  • oil phase can contain typical oil-soluble components
  • water phase can contain typical water-soluble materials.
  • emulsions are preferred because of their desirable aesthetic properties and their utility as vehicles for the dihydroxyacetone and the other essential and optional components of this invention.
  • emulsions can cover a broad range of consistencies including lotions, light creams, heavy creams, and the like.
  • an effective amount of the emulsion is topically applied to human skin.
  • effective is meant an amount sufficient to provide an artificial tan when the composition is topically applied, but not so much as to cause any side effects or skin reactions.
  • Quantities of emulsion which can be topically applied to provide an artificial tan are about, but not limited to, 2 mg/cm 2 . pH Reoeriements
  • the pH of a formulation is an important factor in determining the stability of the dihydroxyacetone. For example, it is well known that dihydroxyacetone rapidly degrades at extremes of alkaline pH. Suppliers of dihydroxyacetone suggest a preferred formulation pH range of between 4 and 6, and recommend the use of a buffer
  • compositions of the instant invention preferably do not contain a buffer, because it has been determined that unbuffered formulations demonstrate improved chemical and physical stability compared to buffered formulations.
  • the unbuffered compositions of the instant invention preferably have a pH range from about 2.5 to about 7, more preferably from about 2.5 to about 6, even more preferably from about 3.5 to about 4.75, and most preferably from about 3.85 to about 4.50.
  • Dihydroxyacetone which is also known as DHA or l,3-dihydroxy-2-propanone, is a white to off-white, crystalline powder having a characteristic sweet, cooling taste.
  • the compound can exist as a mixture of monomers and dimers, with the dimer predominating. Heating or melting dimeric dihydroxyacetone converts the material into the monomeric form. The conversion of the dimer to the monomer also takes place in aqueous solution. See The Merck Index, Tenth Edition, entry 3167, p. 463 (1983), this reference being incorporated herein by reference in its entirety.
  • dihydroxyacetone reacts with the amino acids and amino groups of the skin keratin forming the brown colored compounds which provide an artificial tan. The process takes place in the outer layers of the epidermis. It is believed that the monomer is the active form responsible for this phenomenon. There is much evidence to suggest that the reaction of dihydroxyacetone with the components of the skin is similar to the Maillard Reaction. In this reaction, reducing sugars react with amino acids, proteins, and peptides to form various adducts which are ultimately converted into brown-colored compounds. See V.R. Usdin, Artificial Tanning Preparations, Cosmetics and Toiletries, vol. 91 pp. 29-32 (March 1976), this reference being incorporated herein by reference in its entirety. Dihydroxyacetone is commercially available from E. Merck
  • the dihydroxyacetone of the emulsion compositions of the instant invention is present from about 0.1% to about 20%, more preferably from about 2% to about 7%, and most preferably from about 3% to about 5%.
  • alkyl phosphate An essential component of the present compositions is an alkyl phosphate. These alkyl phosphates correspond to the general formula:
  • R is alkyl or alkenyl having an average of from about 10 to about 20 carbon atoms
  • X is selected from the group consisting of hydrogen, alkali metal, ammonium, and substituted ammonium (e.g. alkylammonium, alkoxylated ammonium, and polyethoxylated ammonium). Mixtures of more than one alkyl phosphate component are useful in the compositions disclosed herein.
  • alkyl phosphates in which R is a C-16 alkyl moiety and X is selected from the group consisting of hydrogen, potassium, ethanolamine, diethanolamine, and triethanolamine.
  • Preferred alkyl phosphates useful in the present invention include potassium cetyl phosphate, ethanolamine cetyl phosphate, diethanolamine cetyl phosphate, triethanolamine cetyl phosphate, cetyl phosphate, and mixtures thereof. Most preferred are potassium cetyl phosphate, diethanolamine cetyl phosphate, cetyl phosphate, and mixtures thereof. Potassium cetyl phosphate (provisional CTFA designation) is commercially available from L.
  • the alkyl phosphate of the instant invention is present from about 0.1% to about 5%, more preferably from about 0.25% to about 1.5%, and most preferably from about 0.5% to about 1.0%.
  • Carboxylic Acid Copolymer is present from about 0.1% to about 5%, more preferably from about 0.25% to about 1.5%, and most preferably from about 0.5% to about 1.0%.
  • compositions of the present invention is a carboxylic acid copolymer (i.e. an acrylic acid copolymer).
  • carboxylic acid copolymer i.e. an acrylic acid copolymer
  • These copolymers consist essentially of a colloidally water-soluble polymer of acrylic acid crosslinked with a polyalkenyl polyether of a polyhydric alcohol, and optionally an acrylate ester or a polyfunctional vinylidene monomer.
  • Preferred copolymers useful in the present invention are polymers of a monomeric mixture containing 95.9 to 98.8 weight percent of an olefinically unsaturated carboxylic monomer selected from the group consisting of acrylic, methacrylic and ethacrylic acids; about 1 to about 3.5 weight percent of an acrylate ester of the formula:
  • Rl 0 CH 2 C—C---0—R wherein R is an alkyl radical containing 10 to 30 carbon atoms and Rl is hydrogen, methyl or ethyl; and 0.1 to 0.6 weight percent of a polymerizable cross-l nking polyalkenyl polyether of a polyhydric alcohol containing more than one alkenyl ether group per molecule wherein the parent polyhydric alcohol contains at least 3 carbon atoms and at least 3 hydroxyl groups.
  • these polymers contain from about 96 to about 97.9 weight percent of acrylic acid and from about 2.5 to about 3.5 weight percent of acrylic esters wherein the alkyl group contains 12 to 22 carbon atoms, and R 1 is methyl, most preferably the acrylate ester is stearyl methacrylate.
  • the amount of crosslinking polyalkenyl polyether monomer is from about 0.2 to 0.4 weight percent.
  • the preferred crosslinking polyalkenyl polyether monomers are allyl pentaerythritol, trimethylolpropane diallylether or allyl sucrose.
  • copolymers useful in the present invention are the polymers which contain at least two monomeric ingredients, one being a monomeric olefinically-unsaturated carboxylic acid, and the other being a polyalkenyl, polyether of a polyhydric alcohol. Additional monomeric materials can be present in the monomeric mixture if desired, even in predominant proportion.
  • the first monomeric ingredient useful in the production of these carboxylic polymers are the olefinically-unsaturated carboxylic acids containing at least one activated carbon-to-carbon olefinic double bond, and at least one carboxyl group.
  • Another useful carboxylic monomer is maleic anhydride or the acid. The amount of acid used will be from about 95.5 to about 98.9 weight percent of the total monomers used. More preferably the range will be from about 96 to about 97.9 weight percent.
  • the second monomeric ingredient useful in the production of these carboxylic polymers are the polyalkenyl polyethers having more than one alkenyl ether grouping per molecule.
  • the most useful possess alkenyl groups in which an olefinic double bond is present attached to a terminal methylene grouping, CH2 C ⁇ .
  • the additional monomeric materials which can be present in the polymers include polyfunctional vinylidene monomers containing at least two terminal CH2 ⁇ groups, including for example, butadiene, isoprene, divinyl benzene, divinyl naphthalene, allyl acrylates, and the like. These polymers are fully described in U.S. Patent 2,798,053, to Brown, H.P., issued July 2, 1957, this patent being incorporated herein by reference.
  • carboxylic acid copolymers useful in the present invention include Carbomer 934, Carbomer 941, Carbomer 950, Carbomer 951, Carbomer 954, Carbomer 980, Carbomer 981, Carbomer 1342, and Acrylates/C ⁇ o-30 Alkyl Acrylate Cross Polymers (available as CarbopolR 934, CarbopolR 941, CarbopolR 950, CarbopolR 951, CarbopolR 954, CarbopolR 980, CarbopolR 981, CarbopolR 1342, and the Pemulen Series, respectively, from B.F. Goodrich).
  • carboxylic acid copolymers useful in the present invention include sodium salts of acrylic acid/acrylamide copolymers sold by the Hoechst Celanese Corporation under the trademark of Hostaceren PN73. Also included are the hydrogel polymers sold by Lipo Chemicals Inc. under the trademark of HYPAN hydrogels. These hydrogels consist of crystalline pucks of nitrites on a C-C backbone with various other pendant groups such as carboxyls, amides, and amidines. An example would include HYPAN SA100 H, a polymer powder available from Lipo Chemical.
  • the carboxylic acid copolymers can be used individually or as a mixture of two or more polymers and comprise from about 0.025% to about 2.00%, preferably from about 0.1% to about 1.50% and most preferably from about 0.40% to about 1.25% percent of the compositions of the present invention.
  • compositions of the instant invention are present in a proper ratio.
  • the ratio of the total amount of alkyl phosphate to carboxylic acid copolymer should be from about 5:1 to about 1:5, more preferably from about 2.5:1 to about 1:2.5, and most preferably from about 1.5:1 to about 1:1.5.
  • Each of the water and oil phases of the oil-in-water emulsions can comprise a wide variety of optional components. Typical of such optional components are: Sunscreens
  • sunscreening agents include, but are not limited to, for example: Ethylhexyl-p-methoxycinnamate (available as Parsol MCX from Givaudan Corporation), p-Aminobenzoic acid, its salts and its derivatives (ethyl, isobutyl, glyceryl esters; p-dimethylaminobenzoic acid; 2-ethylhexyl N,N-dimethylaminobenzoate); p-Methoxycinnamic Acid Diethanolamine Salt (available as Bernel Hydro from Bernel Chemical Co.); Anthranilates (i.e., o-aminobenzoates; methyl, octyl, a yl , menthyl,
  • sunscreens include the solid physical sunblocks such as titanium dioxide (micronized titanium dioxide, 0.03 microns), zinc oxide, silica, iron oxide and the like. Without being limited by theory, it is believed that these inorganic materials provide a sunscreening benefit through reflecting, scattering, and absorbing harmful UV, visible, and infrared radiation.
  • a safe and photoprotectively effective amount of sunscreen(s) can be used in the artificial tanning emulsions of the present invention.
  • safe and photoprotectively is meant an amount sufficient to provide photoprotection when the composition is applied, but not so much as to cause any side effects or skin reactions.
  • the sunscreen(s) can comprise from about 0.5% to about 20% of the composition. Exact amounts will vary depending upon the sunscreen chosen and the desired Sun Protection Factor (SPF). SPF is a commonly used measure of photoprotection of a sunscreen against erythema. See Federal Register, Vol. 43, No. 166, pp. 38206-38269, August 25, 1978.
  • sunscreens are those disclosed in U.S. Patent 4,937,370, to Sabatelli, issued June 26, 1990; and U.S. Patent 4,999,186, to Sabatelli et al., issued March 12, 1991; these two references being incorporated by reference herein.
  • the sunscreening agents disclosed therein have, in a single molecule, two distinct chromophore moieties which exhibit different ultra-violet radiation absorption spectra.
  • One of the chromophore moieties absorbs pre ⁇ dominantly in the UVB radiation range and the other absorbs strongly in the UVA radiation range.
  • sunscreening agents provide higher efficacy, broader UV absorption, lower skin penetration and longer lasting efficacy rela ⁇ tive to conventional sunscreens.
  • Preferred members of this class of sunscreening agents are 4- N,N-(2-ethylhexyl)methylaminobenzoic acid ester of 2,4-dihydroxybenzophenone; N,N-di-(2-ethylhexyl)-4-aminobenzoic acid ester with 4-hydroxydibenzoylmethane; 4-N,N(2-ethylhexyl) methylaminobenzoic acid ester with 4-hydroxydibenzoylmethane; 4-N,N-(2-ethylhexyl)methylaminobenzoic acid ester of 2-hydroxy-4-(2-hydroxyethoxy)benzophenone; 4-N,N-(2-ethylhexyl) methylaminobenzoic acid ester of 4-(2-hydroxyeth- oxy)dibenzoylmethane; N-N-di-(2-ethylhexyl)-4-aminobenzoic acid ester of 2-hydroxy-4
  • the artifical tanning compositions of the instant invention can also contain one or more humectants/moisturizers.
  • humectants/moisturizers can be employed and can be present at a level of from about 1% to about 30%, more preferably from about 2% to about 8% and most preferably from about 3% to about 5%.
  • These materials include urea; guanidine; glycolic acid and glycolate salts (e.g. ammonium and quaternary alkyl ammonium); lactic acid and lactate salts (e.g.
  • ammonium and quaternary alkyl ammonium include polyhydroxy alcohols such as sorbitol, glycerin, hexanetriol, propylene glycol, hexylene glycol and the like; polyethylene glycol; sugars and starches; sugar and starch derivatives (e.g. alkoxylated glucose); D-panthenol ; hyaluronic acid; lactamide monoethanolamine; acetamide monoethanolamine; and mixtures thereof.
  • Preferred humectants/moisturizers for use in the compositions of the present invention are the C3-C6 diols and triols. Especially preferred is the triol, glycerin.
  • Emollients are the C3-C6 diols and triols. Especially preferred is the triol, glycerin.
  • compositions of the present invention can also optionally comprise at least one emollient.
  • suitable emollients include, but are not limited to, volatile and non-volatile silicone oils, highly branched hydrocarbons, and non-polar fatty acid and fatty alcohol esters, and mixtures thereof.
  • Emollients useful in the instant invention are further described in U.S. Patent No. 4,919,934, to Deckner et al., issued April 24 1990, which is incorporated herein by reference in its entirety.
  • the emollients can typically comprise in total from about 1% to about 50%, preferably from about 1% to about 25%, and more preferably from about 1% to about 10% by weight of the compositions of the present invention.
  • E ulsifiers can typically comprise in total from about 1% to about 50%, preferably from about 1% to about 25%, and more preferably from about 1% to about 10% by weight of the compositions of the present invention.
  • compositions of the present invention can also comprise additional emulsifiers and surfactants.
  • Suitable emulsifiers can include, but are not limited to, polyethylene glycol 20 sorbitar. monolaurate (Polysorbate 20), polyethylene glycol 5 soya sterol .
  • compositions of the present invention can also be included in the compositions of the present invention.
  • Non-limiting examples include Vitamin A, and derivatives thereof, ascorbic acid, Vitamin B, biotin, Vitamin D, Vitamin E and derivatives thereof such as tocopheryl acetate, panthothenic acid, and mixtures thereof can also be used.
  • Other Optional Components include Vitamin A, and derivatives thereof, ascorbic acid, Vitamin B, biotin, Vitamin D, Vitamin E and derivatives thereof such as tocopheryl acetate, panthothenic acid, and mixtures thereof can also be used.
  • Other Optional Components include Vitamin A, and derivatives thereof, ascorbic acid, Vitamin B, biotin, Vitamin D, Vitamin E and derivatives thereof such as tocopheryl acetate, panthothenic acid, and mixtures thereof can also be used.
  • Other Optional Components include Vitamin A, and derivatives thereof, ascorbic acid, Vitamin B, biotin, Vitamin D, Vitamin E and derivatives thereof such as tocopheryl
  • additional ingredients can be incorporated into the emulsion compositions of the present invention.
  • additional ingredients include various polymers for aiding the film-forming properties and substantivity of the formulation; gums, resins, and thickeners; preservatives for maintaining the antimicrobial integrity of the compositions; antioxidants; chelators and sequestrants; and agents suitable for aesthetic purposes such as fragrances, pigments, and colorings.
  • Ingredients are identified by chemical or CTFA name.
  • An oil-in-water emulsion is prepared by combining the following components utilizing conventional mixing techniques. Ingredients % Weight
  • Phase A ingredients are dispersed in the water and heated to 75-85°C.
  • Phase B ingredients are combined and heated to 85-90°C until melted.
  • the DEA-Cetyl Phosphate is added to the liquid Phase B and stirred until dissolved. This mixture is then added to Phase A to form the emulsion.
  • the emulsion is cooled to 40-45°C with continued mixing.
  • the dihydroxyacetone is dissolved in water and the resulting solution is mixed into the emulsion.
  • the Phase E ingredients are heated with mixing to 40-45°C until a clear solution is formed and this solution is then added to the emulsion.
  • the Phase F ingredients are added to the emulsion with mixing, which is then cooled to 30-35°C, and then to room temperature.
  • This emulsion is useful for topical application to the skin to provide an artificial tan.
  • An oil-in-water emulsion is prepared by combining the following components utilizing conventional mixing techniques. n redients % Weight
  • An emulsion is prepared from the above ingredients employing the method described in Example I.
  • This emulsion is useful for topical application to the skin to provide an artificial tan.
  • An oil-in-water emulsion is prepared by combining the following components utilizing conventional mixing techniques. Ingredients % Weight
  • An emulsion is prepared from the above ingredients employing the method described in Example I.
  • This emulsion is useful for topical application to the skin to provide an artificial tan and to provide protection to the skin from the harmful effects of ultraviolet radiation.
  • An oil-in-water emulsion is prepared by combining the following components utilizing conventional mixing techniques. Ingredients % Weight Phase A
  • An emulsion is prepared from the above ingredients employing the method described in Example I.
  • SUBSTITUTE SHEET This emulsion is useful for topical application to the skin to provide an artificial tan and to provide protection to the skin from the harmful effects of ultraviolet radiation.
  • An oil-in-water emulsion is prepared by combining the following components utilizing conventional mixing techniques.
  • An emulsion is prepared from the above ingredients employing the method described in Example I.
  • This emulsion is useful for topical application to the skin to provide an artificial tan and to provide protection to the skin from the harmful effects of ultraviolet radiation.

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Abstract

Compositions émulsionnées stabilisées destinées à donner à la peau humaine un hâle artificiel. Lesdites émulsions contiennent de la dihydroxyacétone, au moins un phosphate d'alkyle et au moins un copolymère d'acide carboxylique, la proportion de phosphate d'alkyle par rapport au copolymère d'acide carboxylique étant d'environ 5:1 à environ 1:5. Dans d'autres modes de réalisation, ces compositions émulsionnées contiennent un ou plusieurs écrans solaires et sont également utiles pour protéger la peau humaine des effets nocifs de la lumière solaire et d'autres sources de rayonnement ultraviolet. Des méthodes de préparation de ces compositions, des méthodes destinées à conférer un hâle artificiel à la peau humaine et des méthodes de protection de la peau humaine contre les effets nocifs du rayonnement ultraviolet sont également décrites.
PCT/US1992/001980 1991-04-03 1992-03-13 Compositions emulsionnees stabilisees destinees a donner a leur peau humaine un hale artificiel WO1992017159A2 (fr)

Applications Claiming Priority (2)

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US67989291A 1991-04-03 1991-04-03
US679,892 1991-04-03

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WO1992017159A3 WO1992017159A3 (fr) 1993-01-07

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CN (1) CN1066182A (fr)
AU (1) AU1775592A (fr)
IE (1) IE921053A1 (fr)
MA (1) MA22491A1 (fr)
MX (1) MX9201525A (fr)
PT (1) PT100338A (fr)
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Cited By (31)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0576188A1 (fr) * 1992-06-17 1993-12-29 Unilever Plc Compositions auto-bronzantes
FR2698267A1 (fr) * 1992-11-24 1994-05-27 Oreal Compositions à base de dihydroxyacétone et leur utilisation cosmétique.
WO1994023693A1 (fr) * 1993-04-16 1994-10-27 The Procter & Gamble Company Composition de bronzage artificiel et de protection de la peau contre les radiations uv
US5443759A (en) * 1992-02-29 1995-08-22 Tioxide Specialties Limited Oil-in-water emulsions
FR2719217A1 (fr) * 1994-04-28 1995-11-03 Merck Patent Gmbh Préparation pour la coloration de la peau.
US5514437A (en) * 1994-03-29 1996-05-07 The Procter & Gamble Company Artificial tanning compositions having improved stability
US5543135A (en) * 1992-02-29 1996-08-06 Tioxide Specialties Limited Water-in-oil emulsions
EP0729744A1 (fr) * 1995-03-03 1996-09-04 Roussel-Uclaf Composition cosmétiques pour la protection solaire
AU672022B2 (en) * 1992-07-16 1996-09-19 Glaxo Group Limited Antiviral combinations
US5603863A (en) * 1993-03-01 1997-02-18 Tioxide Specialties Limited Water-in-oil emulsions
US5603923A (en) * 1994-03-29 1997-02-18 The Procter & Gamble Company Artificial tanning compositions having improved color development
WO1997025970A1 (fr) * 1996-01-17 1997-07-24 Lancaster Group Gmbh Agent cosmetique autobronzant a effet de protection solaire
US5747012A (en) * 1993-06-11 1998-05-05 Tioxide Specialties Limited Compositions containing sunscreens
US5776485A (en) * 1991-10-16 1998-07-07 Richardson-Vicks Inc. Enhanced skin penetration system for improved topical delivery of drugs
WO1999006010A2 (fr) * 1997-07-28 1999-02-11 Lancaster Group Gmbh Emulsion huile dans eau cosmetique decorative
WO1999015144A1 (fr) * 1997-09-24 1999-04-01 The B.F.Goodrich Company Composition de filtre solaire
WO1999024006A1 (fr) * 1997-11-12 1999-05-20 Merck Patent Gmbh Formulation cosmetique stable contenant du butylmethoxydibenzoylmethane
SG94678A1 (en) * 1993-01-11 2003-03-18 Procter & Gamble Cosmetic compositions containing surface treated pigments
EP1967174A3 (fr) * 2007-03-01 2008-09-17 Johnson & Johnson Industrial Ltda. Composition auto-bronzante, utilisation de DHA en combinaison, utilisation de DHA en combinaison avec de l'huile minérale, et procédé d'auto-bronzage de la peau
WO2009095197A3 (fr) * 2008-01-31 2010-02-25 Clariant International Ltd Compositions renfermant des esters d'acide phosphorique et des polymères anioniques réticulés, modifiés hydrophobes
WO2011064227A3 (fr) * 2009-11-30 2011-09-15 Unilever Plc Compositions et procédés pour un bronzage sans soleil
WO2011116868A2 (fr) * 2010-03-26 2011-09-29 Merck Patent Gmbh Préparations contenant de la dihydroxyacétone
US8389756B2 (en) 2007-08-02 2013-03-05 Clariant Finance (Bvi) Limited Method for producing alkoxylated phosphoric acid triesters
US8686033B2 (en) 2007-08-02 2014-04-01 Clariant Finance (Bvi) Limited Phosphoric acid esters containing phosphorus atoms bridged by diol units
US8821839B2 (en) 2010-10-22 2014-09-02 Conopco, Inc. Compositions and methods for imparting a sunless tan with a vicinal diamine
US8961942B2 (en) 2011-12-13 2015-02-24 Conopco, Inc. Sunless tanning compositions with adjuvants comprising sulfur comprising moieties
EP3554461B1 (fr) 2016-12-16 2021-03-24 L'oreal Composition cosmétique comprenant des corps gras solides et un polymère gélifiant
US10959933B1 (en) 2020-06-01 2021-03-30 The Procter & Gamble Company Low pH skin care composition and methods of using the same
US11110049B2 (en) 2017-06-23 2021-09-07 The Procter & Gamble Company Composition and method for improving the appearance of skin
US11583488B2 (en) 2020-06-01 2023-02-21 The Procter & Gamble Company Method of improving penetration of a vitamin B3 compound into skin
US11622963B2 (en) 2018-07-03 2023-04-11 The Procter & Gamble Company Method of treating a skin condition

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1481663A1 (fr) * 2003-05-27 2004-12-01 The Procter & Gamble Company Composition cosmétique stable contenant un agent autobronzant

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0227012A1 (fr) * 1985-12-23 1987-07-01 Kao Corporation Emulsion gélatineuse et émulsions eau dans huile obtenues à partir de cette émulsion gélatineuse
EP0265702A2 (fr) * 1986-10-02 1988-05-04 Kao Corporation Composition cosmétique transparente ou semi-transparente à consistance gélifiée
EP0404331A2 (fr) * 1989-06-22 1990-12-27 Unilever Plc Composition cosmétique
EP0425324A1 (fr) * 1989-08-29 1991-05-02 L'oreal Composition pour la coloration de la peau à base de dérivés indoliques et d'hydroxyacétone

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0227012A1 (fr) * 1985-12-23 1987-07-01 Kao Corporation Emulsion gélatineuse et émulsions eau dans huile obtenues à partir de cette émulsion gélatineuse
EP0265702A2 (fr) * 1986-10-02 1988-05-04 Kao Corporation Composition cosmétique transparente ou semi-transparente à consistance gélifiée
EP0404331A2 (fr) * 1989-06-22 1990-12-27 Unilever Plc Composition cosmétique
EP0425324A1 (fr) * 1989-08-29 1991-05-02 L'oreal Composition pour la coloration de la peau à base de dérivés indoliques et d'hydroxyacétone

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
BALSAM M. 'cosmetics , science and technology' 10 December 1973 , WILEY-INTERSCIENCE , NEW YORK LONDON 2 de edition *

Cited By (47)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5874095A (en) * 1991-10-16 1999-02-23 Richardson-Vicks Inc. Enhanced skin penetration system for improved topical delivery of drugs
US5776485A (en) * 1991-10-16 1998-07-07 Richardson-Vicks Inc. Enhanced skin penetration system for improved topical delivery of drugs
US5443759A (en) * 1992-02-29 1995-08-22 Tioxide Specialties Limited Oil-in-water emulsions
US5516457A (en) * 1992-02-29 1996-05-14 Tioxide Specialties Limited Oil-in-water emulsions
US5543135A (en) * 1992-02-29 1996-08-06 Tioxide Specialties Limited Water-in-oil emulsions
EP0576188A1 (fr) * 1992-06-17 1993-12-29 Unilever Plc Compositions auto-bronzantes
AU672022B2 (en) * 1992-07-16 1996-09-19 Glaxo Group Limited Antiviral combinations
FR2698267A1 (fr) * 1992-11-24 1994-05-27 Oreal Compositions à base de dihydroxyacétone et leur utilisation cosmétique.
EP0604249A1 (fr) * 1992-11-24 1994-06-29 L'oreal Compositions à base de dihydroxyacétone et leur utilisation cosmétique
AU680633B2 (en) * 1992-11-24 1997-08-07 L'oreal Compositions based on dihydroxyacetone and their cosmetic use
SG94678A1 (en) * 1993-01-11 2003-03-18 Procter & Gamble Cosmetic compositions containing surface treated pigments
US5603863A (en) * 1993-03-01 1997-02-18 Tioxide Specialties Limited Water-in-oil emulsions
WO1994023693A1 (fr) * 1993-04-16 1994-10-27 The Procter & Gamble Company Composition de bronzage artificiel et de protection de la peau contre les radiations uv
US5700452A (en) * 1993-04-16 1997-12-23 The Procter & Gamble Company Compositions for imparting an artificial tan and protecting the skin from ultra-violet radiation
US5747012A (en) * 1993-06-11 1998-05-05 Tioxide Specialties Limited Compositions containing sunscreens
US5514437A (en) * 1994-03-29 1996-05-07 The Procter & Gamble Company Artificial tanning compositions having improved stability
US5603923A (en) * 1994-03-29 1997-02-18 The Procter & Gamble Company Artificial tanning compositions having improved color development
FR2719217A1 (fr) * 1994-04-28 1995-11-03 Merck Patent Gmbh Préparation pour la coloration de la peau.
EP0729744A1 (fr) * 1995-03-03 1996-09-04 Roussel-Uclaf Composition cosmétiques pour la protection solaire
FR2731152A1 (fr) * 1995-03-03 1996-09-06 Roussel Uclaf Compositions cosmetiques pour la protection solaire
WO1997025970A1 (fr) * 1996-01-17 1997-07-24 Lancaster Group Gmbh Agent cosmetique autobronzant a effet de protection solaire
US6007796A (en) * 1996-01-17 1999-12-28 Lancaster Group Gmbh Cosmetic self-tanning agent having a sunscreen effect
EA000809B1 (ru) * 1996-01-17 2000-04-24 Ланкастер Гроуп Гмбх Косметическое средство для самозагара со светозащитным действием
WO1999006010A2 (fr) * 1997-07-28 1999-02-11 Lancaster Group Gmbh Emulsion huile dans eau cosmetique decorative
WO1999006010A3 (fr) * 1997-07-28 1999-06-10 Lancaster Group Gmbh Emulsion huile dans eau cosmetique decorative
WO1999015144A1 (fr) * 1997-09-24 1999-04-01 The B.F.Goodrich Company Composition de filtre solaire
US6464965B1 (en) 1997-09-24 2002-10-15 Noveon Ip Holdings Corp. Sunscreen composition
WO1999024006A1 (fr) * 1997-11-12 1999-05-20 Merck Patent Gmbh Formulation cosmetique stable contenant du butylmethoxydibenzoylmethane
US6491930B2 (en) 1997-11-12 2002-12-10 Merck Patent Gesellschaft Mit Stable cosmetic formulation containing butylmethoxydibenzoylmethane
EP1967174A3 (fr) * 2007-03-01 2008-09-17 Johnson & Johnson Industrial Ltda. Composition auto-bronzante, utilisation de DHA en combinaison, utilisation de DHA en combinaison avec de l'huile minérale, et procédé d'auto-bronzage de la peau
US8841475B2 (en) 2007-08-02 2014-09-23 Clariant Finance (Bvi) Limited Method for producing alkoxylated phosphoric acid triesters
US8389756B2 (en) 2007-08-02 2013-03-05 Clariant Finance (Bvi) Limited Method for producing alkoxylated phosphoric acid triesters
US8686033B2 (en) 2007-08-02 2014-04-01 Clariant Finance (Bvi) Limited Phosphoric acid esters containing phosphorus atoms bridged by diol units
WO2009095197A3 (fr) * 2008-01-31 2010-02-25 Clariant International Ltd Compositions renfermant des esters d'acide phosphorique et des polymères anioniques réticulés, modifiés hydrophobes
WO2011064227A3 (fr) * 2009-11-30 2011-09-15 Unilever Plc Compositions et procédés pour un bronzage sans soleil
GB2508329B (en) * 2009-11-30 2014-12-10 Unilever Plc Compositions and methods for imparting a sunless tan
GB2508329A (en) * 2009-11-30 2014-06-04 Unilever Plc Compositions and methods for imparting a sunless tan
WO2011116868A2 (fr) * 2010-03-26 2011-09-29 Merck Patent Gmbh Préparations contenant de la dihydroxyacétone
WO2011116868A3 (fr) * 2010-03-26 2012-05-10 Merck Patent Gmbh Préparations contenant de la dihydroxyacétone
US8821839B2 (en) 2010-10-22 2014-09-02 Conopco, Inc. Compositions and methods for imparting a sunless tan with a vicinal diamine
US8961942B2 (en) 2011-12-13 2015-02-24 Conopco, Inc. Sunless tanning compositions with adjuvants comprising sulfur comprising moieties
EP3554461B1 (fr) 2016-12-16 2021-03-24 L'oreal Composition cosmétique comprenant des corps gras solides et un polymère gélifiant
US11110049B2 (en) 2017-06-23 2021-09-07 The Procter & Gamble Company Composition and method for improving the appearance of skin
US11622963B2 (en) 2018-07-03 2023-04-11 The Procter & Gamble Company Method of treating a skin condition
US10959933B1 (en) 2020-06-01 2021-03-30 The Procter & Gamble Company Low pH skin care composition and methods of using the same
US11583488B2 (en) 2020-06-01 2023-02-21 The Procter & Gamble Company Method of improving penetration of a vitamin B3 compound into skin
US11911498B2 (en) 2020-06-01 2024-02-27 The Procter & Gamble Company Low pH skin care composition and methods of using the same

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IE921053A1 (en) 1992-10-07
MA22491A1 (fr) 1992-12-31
MX9201525A (es) 1992-10-01
WO1992017159A3 (fr) 1993-01-07
CN1066182A (zh) 1992-11-18
AU1775592A (en) 1992-11-02
PT100338A (pt) 1993-10-29
TR25613A (tr) 1993-07-01

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