WO2000028960A1 - Emulsion de type aqueux contenant un compose d'acide ascorbique - Google Patents

Emulsion de type aqueux contenant un compose d'acide ascorbique Download PDF

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Publication number
WO2000028960A1
WO2000028960A1 PCT/US1998/024255 US9824255W WO0028960A1 WO 2000028960 A1 WO2000028960 A1 WO 2000028960A1 US 9824255 W US9824255 W US 9824255W WO 0028960 A1 WO0028960 A1 WO 0028960A1
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WO
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Prior art keywords
oil
emulsion
compound
water
ascorbic acid
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PCT/US1998/024255
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English (en)
Inventor
Asako Yamaguchi
Toru Sumiyoshi
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The Procter & Gamble Company
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Application filed by The Procter & Gamble Company filed Critical The Procter & Gamble Company
Priority to BR9816071-0A priority Critical patent/BR9816071A/pt
Priority to CA002350407A priority patent/CA2350407A1/fr
Priority to CZ20011527A priority patent/CZ20011527A3/cs
Priority to AU14071/99A priority patent/AU1407199A/en
Priority to KR1020017006054A priority patent/KR20010107964A/ko
Priority to PCT/US1998/024255 priority patent/WO2000028960A1/fr
Priority to JP2000582008A priority patent/JP2003502275A/ja
Priority to EP98957932A priority patent/EP1128805A1/fr
Priority to CN98814310A priority patent/CN1356888A/zh
Publication of WO2000028960A1 publication Critical patent/WO2000028960A1/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
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/67—Vitamins
    • 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
    • A61K8/062—Oil-in-water 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
    • A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
    • A61K8/26—Aluminium; Compounds thereof
    • 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
    • A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
    • A61K8/27—Zinc; Compounds thereof
    • 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
    • A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
    • A61K8/28—Zirconium; Compounds thereof
    • 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
    • A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
    • A61K8/29—Titanium; Compounds thereof
    • 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
    • A61K8/34—Alcohols
    • A61K8/342—Alcohols having more than seven atoms in an unbroken chain
    • 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
    • A61K8/676—Ascorbic acid, i.e. vitamin C
    • 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
    • A61K8/73—Polysaccharides
    • 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
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/02—Preparations for care of the skin for chemically bleaching or whitening the skin

Definitions

  • the present invention relates to a topical composition.
  • it relates to a topical skin lightening emulsion.
  • Rough and/or broken skin and hyperpigmentations are areas consumers typically seek to treat. Skin lightening is of particular interest in certain Asian populations.
  • UV rays Irradiation of ultra-violet (UV) rays tends to cause sun-burning, resulting in skin darkening and/or hyperpigmentation. It is generally known that conditions which result in defective or missing tyrosinase, an enzyme involved in the formation of melanin, lead to hyperpigmentation, e.g. albinism.
  • the irradiation of UV rays as a consequence of exposure to sunlight promotes a melanin complex formation in melanocytes located in the basal layer of the epidermis. Melanin is subsequently released from the dendrites of the melanocytes, then diffused to keratinocytes, resulting in hyperpigmentation of the skin.
  • hyperpigmentation may take the form of spots, freckles, blotches, unwelcome general darkening and/or unevenness of the basal skin.
  • a wide variety of compounds and/or ingredients e.g., ascorbic acid and derivatives thereof, kojic acid and derivatives thereof, hydroquinone, arbutine, and a variety of extracts such as glycyrrhiza, are known and are commonly- available for skin-lightening use.
  • hi-tech synthetic ingredients useful for skin-lightning are also available in a wide variety and array of product forms.
  • L-ascorbic acids e.g., Vitamin C
  • Vitamin C are useful ingredients as skin lightening and/or evenness agents as well as a reductant, UV-absorbent and melanin- formation inhibitor in cosmetics.
  • GB 2259014-A Hadas et al., issued March 3, 1998, discloses a composition for skin lightening containing oil-soluble ascorbic acid derivatives such as ascorbic palmitate with sun screening agents such as titanium dioxides.
  • L-ascorbic acid tends to be unstable in formulation.
  • increasing the level of L-ascorbic acid in an emulsion- type composition can result in an unstable emulsion.
  • increased levels of L-ascorbic acids tend to cause e.g., decomposition of L-ascorbic acid in the emulsion, imparting a yellowish and/or brownish color to the composition. It would be desired to stabilize the composition containing ascorbic acids, particularly while increasing the levels in emulsion.
  • the present invention is directed to an oil-in-water emulsion comprising:
  • topical application means to apply or spread a material onto the surface of the skin.
  • skin lightening refers altering the appearance of the skin to a brighter, lighter, and/or whiter appearance, and improving hyperpigmentation as compared to pre-treatment.
  • compositions or components thereof so described are suitable for use in contact with human skin without undue toxicity, incompatibility, instability, allergic response, and the like.
  • safety and effective amount means an amount of a compound or composition sufficient to significantly induce a positive benefit, preferably a positive skin appearance or feel benefit, including independently the benefits disclosed herein, but low enough to avoid serious side effects, e.g., to provide a reasonable benefit to risk ratio, within the scope of sound judgment of the skilled artisan.
  • ingredients is meant to include a simple combination of materials and any compounds that may result from their combination. All ingredients such as actives and other ingredients useful herein may be categorized or described by their cosmetic and/or therapeutic benefit or their postulated mode of action. However, it is to be understood that the active and other ingredients useful herein can, in some instances, provide more than one cosmetic and/or therapeutic benefit or operate via more than one mode of action. Therefore, classifications herein are made for the sake of convenience and are not intended to limit an ingredient to the particularly stated application or applications listed.
  • the present invention is directed to an oil-in-water emulsion comprising: (a) a water-soluble ascorbic acid compound; (b) a metallic oxide; (c) a structuring compound; (d) a hydrophobic component; and (e) a hydrophilic liquid carrier.
  • the pH of the emulsion of the present invention is from about 6 to about 10, more preferably from about 7 to about 9.
  • compositions containing the ascorbic acid compound can provide skin benefits such as the prevention of melanin production and the reduction of age spots, blotches and/or freckles associated with skin hyperpigmentation.
  • a structuring compound in emulsion can sustain the original physical properties of a water-soluble ascorbic acid compound and the emulsion thereof, even when the composition contains relatively high levels of the water-soluble ascorbic acid compound.
  • the oil-in-water emulsion of the present invention includes a water-soluble ascorbic acid compound.
  • the water-soluble ascorbic acid compound is selected depending upon its compatibility with the other ingredients.
  • the water-soluble ascorbic acid compound may be included as a substantially pure material, for example, which may be an extract obtained by suitable physical and/or chemical isolation from natural (e.g., plant) sources.
  • the oil-in-water emulsion of the present invention preferably contains from about 1.0% to about 10.0% of a water-soluble ascorbic acid compound, more preferably from about 2.0% to about 5.0%.
  • water-soluble ascorbic acid compound means ascorbic acid or derivatives thereof which have the formula (I):
  • V and W are independently -OH; R is - CH(OH)-CH2OH; and salts thereof.
  • the water-soluble ascorbic acid compound useful herein is an ascorbic acid salt or derivative thereof, such as the non-toxic alkali metal, alkaline earth metal and ammonium salts commonly known by those skilled in the art including, but not limited to, the sodium, potassium, lithium, calcium, magnesium, barium, ammonium and protamine salts which are prepared by methods well known in the art.
  • an ascorbic acid salt or derivative thereof such as the non-toxic alkali metal, alkaline earth metal and ammonium salts commonly known by those skilled in the art including, but not limited to, the sodium, potassium, lithium, calcium, magnesium, barium, ammonium and protamine salts which are prepared by methods well known in the art.
  • the water-soluble ascorbic acid salt useful herein is a metal ascorbate having the following formula (II):
  • R2 and R3 are independently selected from hydrogen and linear or branched alkyl of 1 to about 8 carbons; M is a metal; and x is an integer of from 1 to about 3. More preferably, R ⁇ and R ⁇ are independently selected from hydrogen and linear or branched alkyl of 1 to about 3 carbons; M ⁇ is sodium, potassium, magnesium, or calcium.
  • water-soluble ascorbic acid salts having formula (II) include monovalent metal salts (e.g., sodium ascorbate, potassium ascorbate), divalent metal salts (e.g., magnesium ascorbate, calcium ascorbate) and trivelent metal salts (e.g., aluminum ascorbate) of ascorbic acid.
  • the water-soluble ascorbic acid salt useful herein is a water soluble ascorbyl ester having the following formula (III):
  • A is sulfate or phosphate
  • R 4 and R ⁇ are independently selected from hydrogen and linear or branched alkyl of 1 to about 8 carbons
  • M ⁇ is a metal
  • y is an integer of 1 to about 3. More preferably, R 4 and R5 are independently selected from hydrogen and linear or branched alkyl of 1 to about 3 carbons; M2 is sodium, potassium, magnesium, or calcium.
  • Exemplary water soluble salt derivatives include, but are not limited to, L- ascorbyl phosphate ester salts such as sodium L-ascorbyl phosphate, potassium L-ascorbyl phosphate, magnesium L-ascorbyl phosphate, calcium L-ascorbyl phosphate, aluminum L-ascorbyl phosphate.
  • L-ascorbyl sulfate ester salts can also be used. Examples are sodium L-ascorbyl sulfate, potassium L-ascorbyl sulfate, magnesium L-ascorbyl sulfate, calcium L-ascorbyl sulfate and aluminum L-ascorbyl sulfate.
  • L- ascorbyl phosphate ester salts such as sodium L-ascorbyl phosphate, potassium L-ascorbyl phosphate, magnesium L-ascorbyl phosphate, calcium L-ascorbyl phosphate, aluminum L-
  • the oil-in-water emulsion of the present invention includes a metallic oxide.
  • the metallic oxide useful herein present in the emulsion from about 0.1% to about 5.0%, more preferably from about 0.5% to about 2.0%.
  • the metallic oxide is selected from the group consisting of titanium dioxide, zinc oxide, zirconium dioxide, aluminum oxide, and combinations thereof (combinations are intended to include particles which comprise one or more of these materials, as well as mixtures of these particulate materials), more preferably, titanium dioxide.
  • the metallic oxides useful herein are commercially available from a number of sources.
  • a suitable metallic oxides are TronoxTM (titanium dioxide series) and SAT-T CR837 (rutile Titanium dioxide) available from U. S. Cosmetics, titanium dioxide CR-50 available from Ishihara Sangyo Kaisha, and titanium dioxide JA-1 available from Tayca Corporation.
  • the oil-in-water emulsion of the present invention comprises a structuring compound.
  • structuring compound refers to a compound which forms an organized structure, a gel network system, such that the system can exist in hydrophobic or hydrophilic components. It is believed that the structuring compound assists in providing good rheological characteristics to the composition which contribute to the stability of the emulsion.
  • the structuring compound is present from about 1.0% to about 10.0%, more preferably from about 2.0% to about 8.0% in the composition.
  • the structuring compound comprises a fatty alcohol and an amphiphilic surfactant. While not wishing to be bound by theory, it is believed that the fatty alcohol, together with the amphiphilic surfactant, is oriented in order to form a lamellar structure, resulting in sustaining oil and water phases. It is also believed such an organized structure, called "fatty alcohol gel network system,” contribute to stability of the emulsion.
  • the fatty alcohols useful herein are a saturated, linear or branched fatty alcohol, selected from the group consisting of a saturated, linear or branched C-
  • Preferred fatty alcohols are cetyl alcohol, stearyl alcohol, and mixtures thereof.
  • the fatty alcohols useful herein present from about 1.0% to 10.0% in the composition, more preferably from about 1.0% to about 5.0%.
  • amphiphilic surfactant useful herein includes surfactants, any of a wide variety of nonionic, cationic, anionic, zwitterionic, amphoteric as well as mixtures of these surfactants.
  • additional surfactants useful herein are described in McCutcheon's Detergents and Emulsifiers, North American Edition (1986), published by Allured Publishing Corporation, which is incorporated herein by reference in its entirety. Also see U.S. Patent No. 4,800,197, to Kowcz et al., issued January 24, 1989, which is incorporated herein by reference in its entirety, for exemplary surfactants useful herein.
  • the amphiphilic surfactants useful herein present from about 1.0% to 10.0% in the composition, more preferably from about 2.0% to about 6.0%.
  • the amphiphilic surfactant of the present invention is nonionic surfactants.
  • Preferred nonionic surfactants useful herein are the condensation products of alkylene oxides with both fatty acids and fatty alcohols (e.g., wherein the polyalkylene oxide portion is esterified on one end with a fatty acid and etherified (e.g., connected via an ether linkage) on the other end with a fatty alcohol).
  • R2 and R3 are independently alkyl of from about 10 to about 30 carbons; ⁇ 1 is - OCH2CH2 derived from, for example ethylene glycol or oxide or -O CH2CH CH3- derived from propylene glycol or oxide; and z is an integer from about 6 to about 100.
  • alkylene oxide derived nonionic surfactants include ceteth-6, ceteth-10, ceteth-12, ceteareth-6, ceteareth-10, ceteareth-12, ceteareth-20, steareth-6, steareth-10, steareth-12, steareth-20, steareth-21 , steareth-100, PEG-6 stearate, PEG-10 stearate, PEG-12 stearate, PEG-100 stearate, PEG-10 glyceryl stearate, PEG-20 glyceryl stearate, PEG-30 glyceryl cocoate, PEG-80 glyceryl cocoate, PEG-80 glyceryl tallowate, PEG-200 glyceryl tallowate, PEG-8 dilaurate, PEG-10 distearate, glyceryl monostearate, gylceryl distearate, glyceryl monolaurate, gly
  • the structuring compound may further contain a co-thickener.
  • exemplary co-thickeners useful herein are polysaccharides and materials which are primarily derived from natural sources such as gums.
  • Polysaccharides as used herein means an ingredient containing a backbone of repeating sugar (i.e. carbohydrate) units.
  • Nonlimiting examples of polysaccharide include those selected from the group consisting of cellulose, carboxymethyl hydroxyethylcellulose, cellulose acetate propionate carboxylate, hydroxyethylcellulose, hydroxyethyl ethylcellulose, hydroxypropylcellulose, hydroxypropyl methylcellulose, methyl hydroxyethylcellulose, microcrystalline cellulose, sodium cellulose sulfate, and mixtures thereof.
  • alkyl substituted celluloses are also useful herein.
  • the hydroxy groups of the cellulose polymer is hydroxyalkylated (preferably hydroxyethylated or hydroxypropylated) to form a hydroxyalkylated cellulose which is then further modified with a C-
  • these polymers are ethers of Cio-30 straight or branched chain alcohols with hydroxyalkylcelluloses.
  • alkyl groups useful herein include those selected from the group consisting of stearyl, isostearyl, lauryl, myristyl, cetyl, isocetyl, cocoyl (i.e.
  • alkyl groups derived from the alcohols of coconut oil palmityl, oleyl, linoleyl, linolenyl, ricinoleyl, behenyl, and mixtures thereof.
  • Preferred among the alkyl hydroxyalkyl cellulose ethers is the material given the CTFA designation cetyl hydroxyethylcellulose, which is the ether of cetyl alcohol and hydroxyethylcellulose. This material is sold under the tradename Natrosol® CS Plus from Aqualon Corporation.
  • polysaccharides include scleroglucans comprising a linear chain of (less than 3) linked glucose units with a less than 6 linked glucose every three units, a commercially available example of which is ClearogelTM CS11 from Michel Mercier Products Inc. (Mountainside, NJ).
  • Nonlimiting examples of the gums include materials selected from the group consisting of acacia, agar, algin, alginic acid, ammonium alginate, amylopectin, calcium alginate, calcium carrageenan, carnitine, carrageenan, dextrin, gelatin, gellan gum, guar gum, guar hydroxypropyltrimonium chloride, hectorite, hyaluroinic acid, hydrated silica, hydroxypropyl chitosan, hydroxypropyl guar, karaya gum, kelp, locust bean gum, natto gum, potassium alginate, potassium carrageenan, propylene glycol alginate, sclerotium gum, sodium carboyxmethyl dextran, sodium carrageenan, tragacanth gum, xanthan gum, and mixtures thereof.
  • Hydrophobic components useful in the present invention include a lipid, oil, oily or other hydrophobic component.
  • the hydrophobic component is used as an emollient.
  • suitable hydrophobic components are known and may be used herein and numerous examples can be found in Sagarin, Cosmetics, Science and Technology, 2nd Edition, Vol. 1 , pp. 32-43 (1972).
  • Nonlimiting examples of suitable hydrophobic components include mineral oil, petrolatum, C7.40 straight and branched hydrocarbons, C1-.30 alcohol esters, glycerides, alkylene glycol esters, propoxylated and ethoxylated derivatives, sugar ester, vegetable oils and hydrogenated vegetable oils, animal fats and oils, and C4-.2O alkyl ethers of polypropylene glycols, C1-.20 carboxylic acid esters of polypropylene glycols, and di-Cs-30 alkyl ethers.
  • Examples of hydrophobic components useful herein are set forth in U.S. Patent 5,306,514, Letton et al., issued April 26, 1994; Merck Index, Tenth Edition, Entry 7048, p. 1033 (1983); and International Cosmetic Ingredient Dictionary, Fifth Edition, vol. 1 , p.4 5-417 (1993).
  • a fatty acid sugar ester useful herein is C-
  • the oil-in-water emulsion contains from about 2% to about 20% of the hydrophobic component, more preferably from about 3% to about 10%.
  • the hydrophobic component may include an ingredient derived from animals, plants, or petroleum and which is natural or synthetic (e.g., man-made).
  • E. Hydrophilic Liquid Carrier The oil-in-water emulsion of the present invention contains a hydrophilic liquid carrier (HLC).
  • HLC hydrophilic liquid carrier
  • Preferred HLC can contain a dermatologically acceptable, non-aqueous hydrophilic diluent.
  • Nonlimiting examples of hydrophilic diluents are polyhydhc alcohols such as low molecular weight monovalent alcohols (i.e., C ⁇ _6) and low molecular weight glycols and polyols including propylene glycol, butylene glycol, hexylene glycol, dipropylene glycol, polyethylene glycol (e.g., Molecular Weight 200-1000 g/mole), polypropylene glycol (e.g., Molecular Weight 425-2025 g/mole), glycerol, 1 ,2,4-butanetriol, 1,2,6-hexanetriol, and combinations thereof.
  • polyhydhc alcohols such as low molecular weight monovalent alcohols (i.e., C ⁇ _6) and low molecular weight glycols and polyols including propylene glycol, butylene glycol, hexylene glycol, dipropylene glycol, polyethylene glycol (e.g., Molecular Weight 200-1000 g
  • the oil-in-water emulsion contains from about 60.0% to about 95.0% of HLC, more preferably from about 70.0% to about 85.0%.
  • HLC includes water and one or more water soluble or dispersible ingredients. The exact amount of water in the formulation will vary with the ranges of the required and optional components chosen.
  • the HLC may further contain a pH adjuster.
  • pH adjuster refers to any component which is employed to increase or decrease the overall pH of the composition to an optimum pH, thereby preventing decomposition of ingredients (particularly the ascorbic acid compound).
  • An optimum pH is subject to the selection of the ascorbic acid compound.
  • MAP magnesium L-ascorbyl phosphate
  • Suitable pH adjusters herein include acetate, phosphate, citrate, triethanolamine and carbonate. A combination of the foregoing are often employed to adjust to a specific optimal pH for the emulsion.
  • the total level by weight of emulsion of the pH adjuster is from about 0.01 % to about 5.0%, preferably, from about 0.5% to about 2.0%.
  • the oil-in-water emulsion of the present invention may further comprise other actives capable of functioning in different ways to enhance the benefits of the ascorbic acid compound and/or to provide other benefits.
  • actives capable of functioning in different ways to enhance the benefits of the ascorbic acid compound and/or to provide other benefits.
  • examples of such substances include, but are not limited to, vitamin B3 compound, anti- oxidants/radical scavengers, anti-inflammatory agents, antimicrobial agents, sunscreens and sunblocks, and chelators.
  • Vitamin B3 Compounds The vitamin B3 compound enhances the skin appearance benefits of the present invention, especially in regulating skin condition, including regulating signs of skin aging, more especially wrinkles, lines, and pores.
  • the vitamin B 3 compound preferably present from about 0.01 % to about 50%, more preferably from about 0.1% to about 10%, even more preferably from about 0.5% to about 10%, and still more preferably from about 1 % to about 5%.
  • vitamin B3 compound means a compound having the formula:
  • R is -CONH2 (e.g., niacinamide), -COOH (e.g., nicotinic acid) or - CH2OH (e.g., nicotinyl alcohol); derivatives thereof; and salts of any of the foregoing.
  • -CONH2 e.g., niacinamide
  • -COOH e.g., nicotinic acid
  • CH2OH e.g., nicotinyl alcohol
  • Exemplary derivatives of the foregoing vitamin B3 compounds include nicotinic acid esters, including non-vasodilating esters of nicotinic acid, nicotinyl amino acids, nicotinyl alcohol esters of carboxylic acids, nicotinic acid N-oxide and niacinamide N-oxide.
  • Suitable esters of nicotinic acid include nicotinic acid esters of from 1 to about 22 carbons, preferably 1 to about 16 carbons, more preferably alcohols from about 1 to about 6 carbons.
  • the alcohols are suitably straight-chain or branched chain, cyclic or acyclic, saturated or unsaturated (including aromatic), and substituted or unsubstituted.
  • the esters are preferably non-vasodilating.
  • non-vasodilating means that the ester does not commonly yield a visible flushing response after application to the skin in the subject compositions (the majority of the general population would not experience a visible flushing response, although such compounds may cause vasodilation not visible to the naked eye, i.e., the ester is non-rubifacient).
  • Non-vasodilating esters of nicotinic acid include tocopherol nicotinate and inositol hexanicotinate; tocopherol nicotinate is preferred.
  • derivatives of the vitamin B3 compound are derivatives of niacinamide resulting from substitution of one or more of the amide group hydrogens.
  • Nonlimiting examples of derivatives of niacinamide useful herein include nicotinyl amino acids, derived, for example, from the reaction of an activated nicotinic acid compound (e.g., nicotinic acid azide or nicotinyl chloride) with an amino acid, and nicotinyl alcohol esters of organic carboxylic acids (e.g., 1 to about 18 carbons).
  • nicotinuric acid C8H8N2O3
  • nicotinyl hydroxamic acid C6H6N2O2
  • nicotinyl alcohol esters include nicotinyl alcohol esters of the carboxylic acids salicylic acid, acetic acid, glycolic acid, palmitic acid and the like.
  • vitamin B3 compounds useful herein are 2- chloronicotinamide, 6-aminonicotinamide, 6-methylnicotinamide, n-methyl- nicotinamide, n,n-diethylnicotinamide, n-(hydroxymethyl)-nicotinamide, quinolinic acid imide, nicotinanilide, n-benzylnicotinamide, n-ethylnicotinamide, nifenazone, nicotinaldehyde, isonicotinic acid, methyl isonicotinic acid, thionicotinamide, nialamide, 1-(3-pyridylmethyl) urea, 2-mercaptonicotinic acid, nicomol, and nia
  • Nonlimiting examples of the above vitamin B3 compounds are well known in the art and are commercially available from a number of sources, e.g., the Sigma Chemical Company (St. Louis, MO); ICN Biomedicals, Inc. (Irvin, CA) and Aldrich Chemical Company (Milwaukee, Wl).
  • vitamin B3 compounds may be used herein.
  • Preferred vitamin B3 compounds are niacinamide and tocopherol nicotinate. Niacinamide is more preferred.
  • salts, derivatives, and salt derivatives of niacinamide are preferably those having substantially the same efficacy as niacinamide in the methods of regulating skin condition described herein.
  • Salts of the vitamin B3 compound are also useful herein.
  • Nonlimiting examples of salts of the vitamin B3 compound useful herein include organic or inorganic salts, such as inorganic salts with anionic inorganic species (e.g., chloride, bromide, iodide, carbonate, preferably chloride), and organic carboxylic acid salts (including mono-, di- and tri- C1-.18 carboxylic acid salts, e.g., acetate, salicylate, glycolate, lactate, malate, citrate, preferably monocarboxylic acid salts such as acetate).
  • anionic inorganic species e.g., chloride, bromide, iodide, carbonate, preferably chloride
  • organic carboxylic acid salts including mono-, di- and tri- C1-.18 carboxylic acid salts, e.g., acetate, salicylate, glycolate, lactate, malate, citrate, preferably monocarboxylic acid salts such
  • Wenner "The Reaction of L-Ascorbic and D-losascorbic Acid with Nicotinic Acid and Its Amide", J. Organic Chemistry, Vol. 14, 22-26 (1949). Wenner describes the synthesis of the ascorbic acid salt of niacinamide.
  • the ring nitrogen of the vitamin B3 compound is substantially chemically free (e.g., unbound and/or unhindered), or after delivery to the skin becomes substantially chemically free ("chemically free” is hereinafter alternatively referred to as "uncomplexed”). More preferably, the vitamin B3 compound is essentially uncomplexed. Therefore, if the composition contains the vitamin B3 compound in a salt or otherwise complexed form, such complex is preferably substantially reversible, more preferably essentially reversible, upon delivery of the composition to the skin. For example, such complex should be substantially reversible at a pH of from about 5.0 to about 6.0. Such reversibility can be readily determined by one having ordinary skill in the art.
  • the vitamin B3 compound is substantially uncomplexed in the composition prior to delivery to the skin.
  • Exemplary approaches to minimizing or preventing the formation of undesirable complexes include omission of materials which form substantially irreversible or other complexes with the vitamin B3 compound, pH adjustment, ionic strength adjustment, the use of surfactants, and formulating wherein the vitamin B3 compound and materials which complex therewith are in different phases. Such approaches are well within the level of ordinary skill in the art.
  • the vitamin B3 compound contains a limited amount of the salt form and is more preferably substantially free of salts of a vitamin B 3 compound.
  • the vitamin B3 compound contains less than about 50% of such salt, and is more preferably essentially free of the salt form.
  • the vitamin B3 compound in the compositions hereof having a pH of from about 4 to about 7 typically contain less than about 50% of the salt.
  • the vitamin B3 compound may be included as the substantially pure material, or as an extract obtained by suitable physical and/or chemical isolation from natural (e.g., plant) sources.
  • the vitamin B3 compound is preferably substantially pure, more preferably essentially pure.
  • Anti-Oxidants and Radical Scavengers are especially useful for providing protection against UV radiation which can cause increased scaling or texture changes in the stratum corneum and against other environmental agents which can cause skin damage.
  • Anti-oxidants and radical scavengers such as tocopherol (vitamin E), tocopherol sorbate, tocopherol acetate, other esters of tocopherol, butylated hydroxy benzoic acids and their salts, 6-hydroxy-2,5,7,8-tetramethylchroman-2- carboxylic acid (commercially available under the tradename Trolox®), gallic acid and its alkyl esters, especially propyl gallate, uric acid and its salts and alkyl esters, sorbic acid and its salts, amines (i.e., N,N-diethylhydroxylamine, amino- guanidine), sulfhydryl compounds (i.e., glutathione), dihydroxy fumaric acid and its salts, lycine pidolate, arginine pilolate, nordihydroguaiaretic acid, bioflavonoids, lysine, methionine, proline, superoxide dismutase, sily
  • Preferred anti-oxidants/radical scavengers are selected from tocopherol sorbate and other esters of tocopherol, more preferably tocopherol sorbate.
  • tocopherol sorbate for example, the use of tocopherol sorbate in topical compositions and applicable to the present invention is described in U.S. Patent 4,847,071 , Bissett et al, issued on July 11 , 1989.
  • Anti-inflammatory agents enhance the skin appearance benefits, by for example, contribution of uniformity and acceptable skin tone and/or color.
  • the anti-inflammatory agent includes a steroidal anti- inflammatory agent and an non-steroidal anti-inflammatory agent.
  • Preferred steroidal anti-inflammatory for use is hydrocortisone.
  • Such agents may suitably be obtained as an extract by suitable physical and/or chemical isolation from natural sources (i.e., plants, fungi, by-products of microorganisms).
  • natural sources i.e., plants, fungi, by-products of microorganisms.
  • alpha bisabolol, aloe vera, Manjistha (extracted from plants in the genus Rubia, particularly Rubia Cordifolia), and Guggal (extracted from plants in the genus Commiphora, particularly Commiphora Mukul), kola extract, chamomile, and sea whip extract may be used.
  • Additional anti-inflammatory agents useful herein include compounds of the licorice (the plant genus/species Glycyrrhiza glabra) family, including glycyrrhetic acid, glycyrrhizic acid, and derivatives thereof (e.g., salts and esters).
  • Suitable salts of the foregoing compounds include metal and ammonium salts.
  • Suitable esters include C2-24 saturated or unsaturated esters of the acids, preferably C-J ⁇ J-24- rnore preferably C ⁇ -24-
  • Antimicrobial agents means a compound capable of destroying microbes, preventing the development of microbes or preventing the pathogenic action of microbes. Antimicrobal agents are useful, for example, in controlling acne.
  • Preferred antimicrobial agents useful in the present invention are benzoyl peroxide, erythromycin, tetracycline, clindamycin, azelaic acid, sulfur resorcinol phenoxyethanol, and IrgasanTM DP 300 (Ciba Geigy Corp., U.S.A.).
  • a safe and effective amount of an antimicrobial agent may be added to compositions of the present invention, preferably from about 0.001 % to about 10%, more preferably from about 0.01 % to about 5%, still more preferably from about 0.05% to about 2%.
  • Sunscreens and Sunblocks generally prevent excessive scaling and texture changes of the stratum corneum by exposure of ultraviolet light and may be added to the composition of the present invention.
  • Suitable sunscreens and sunblocks may be organic or inorganic.
  • sunscreens and sunblocks which are useful in the compositions are those selected from 2-ethylhexyl-p-methoxycinnamate (commercially available as PARSOL MCX), butylmethoxydibenzoyl-methane, 2-hydroxy-4-methoxybenzo- phenone, 2-phenylbenzimidazole-5-sulfonic acid, octyldimethyl-p-aminobenzoic acid, octocrylene, 2-ethylhexyl N,N-dimethyl-p-aminobenzoate, p-aminobenzoic acid, 2-phenylbenzimidazole-5-sulfonic acid, octocrylene, oxybenzone, homomenthyl salicylate, octyl salicylate, 4,4'-methoxy-t-butyldibenzoylmethane, 4-isopropyl dibenzoylmethane, 3-benzy
  • sunscreens and sunblocks such as those disclosed in U.S. Patent 4,937,370, Sabatelli, issued on June 26, 1990, and U.S. Patent 4,999,186, Sabatelli, issued on March 12, 1991.
  • the sunscreens and sunblocks disclosed therein have, in a single molecular, two distinct chromophore moieties which exhibit different ultraviolet radiation absorption spectra.
  • One of the chromophore moieties absorbs predominantly in the UVB radiation range and the other absorbs strongly in the UVA radiation range.
  • These sunscreens and sunblocks provide higher efficacy, broader UV absorption, lower skin penetration and longer lasting efficacy relative to conventional sunscreens and sunblocks.
  • SPF Sun Protection Factor
  • a sunscreen or sunblock herein may also be added to improve the skin, particularly to enhance their resistance to being washed off by water, or rubbed off.
  • Preferred sunscreens and sunblocks which will provide this benefit are a copolymer of ethylene and acrylic acid. Compositions comprising this copolymer are disclosed in U.S. Patent 4,663,157, Brock, issued May 5, 1987.
  • chelator refers to a compound that reacts for removing a metal ion from a system by forming a complex so that the metal ion cannot readily participate in or catalyze chemical reactions.
  • the inclusion of a chelator is especially useful for providing protection against UV radiation which can contribute to excessive scaling or skin texture changes and against other environmental agents which can cause skin damage.
  • Preferred chelators are furildioxime and derivatives thereof.
  • composition of the present invention may further include preservatives and preservative enhancers such as water-soluble or solubilizable preservatives including Germall 115, methyl, ethyl, propyl and butyl esters of hydroxybenzoic acid, benzyl alcohol, EDTA, Bronopol (2-bromo-2-nitropropane-1 ,3-diol) and phenoxypropanol; other skin lightening/evenness agents including kojic acid, arbutin; WO95/23780, Kvalnes et al, published September 8, 1995; skin- conditioning agents; skin penetration enhancing agents; skin protectants; skin soothing agents; skin healing agents; ultraviolet light absorbers or scattering agents; sequestrants; anti-acne agents; anti-androgens; depilation agents; keratolytic agents/ desquamation agents/ exfoliants such as salicylic acid; panthenol moisturizer such as D-pan
  • the oil-in-water emulsions of the present invention are generally prepared by any method conventionally used for providing skin care compositions, particularly for skin lotions, that are known in the art. Such methods typically involve mixing of the ingredients in one or more steps to a relatively uniform state, with or without heating, cooling, and the like. Typical methods are described in, for example are described in Harry's Cosmeticology, 7th Ed., Harry & Wilkinson (Hill Publishers, London 1982).
  • compositions shown below can be prepared by any conventional method known in the art. Suitable methods and formulations are as follows:
  • oil-in-water emulsion above described are suitably made as follows:
  • the composition herein contains increased levels of ascorbic acid compound for skin lightening, while exhibiting improved product aesthetic such as product appearance unchanging to yellow or brown, even if maintained in storage for extended periods of time.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
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  • Epidemiology (AREA)
  • Chemical & Material Sciences (AREA)
  • Inorganic Chemistry (AREA)
  • Dermatology (AREA)
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  • Oil, Petroleum & Natural Gas (AREA)
  • Dispersion Chemistry (AREA)
  • Cosmetics (AREA)
  • Colloid Chemistry (AREA)

Abstract

L'invention se rapporte à une émulsion de type aqueux comportant (a) un composé d'acide ascorbique soluble dans l'eau; (b) un oxyde métallique; (c) un composé structurant; (d) un composant hydrophobe et (e) un excipient liquide hydrophile. Cette composition possède un pH compris entre 6 environ et 10 environ.
PCT/US1998/024255 1998-11-13 1998-11-13 Emulsion de type aqueux contenant un compose d'acide ascorbique WO2000028960A1 (fr)

Priority Applications (9)

Application Number Priority Date Filing Date Title
BR9816071-0A BR9816071A (pt) 1998-11-13 1998-11-13 Emulsão de óleo-em-água contendo um composto de ácido ascórbico
CA002350407A CA2350407A1 (fr) 1998-11-13 1998-11-13 Emulsion de type aqueux contenant un compose d'acide ascorbique
CZ20011527A CZ20011527A3 (cs) 1998-11-13 1998-11-13 Emulze olej ve vodě
AU14071/99A AU1407199A (en) 1998-11-13 1998-11-13 An oil-in-water emulsion containing an ascorbic acid compound
KR1020017006054A KR20010107964A (ko) 1998-11-13 1998-11-13 아스코르브산 화합물을 함유하는 수중유 에멀젼
PCT/US1998/024255 WO2000028960A1 (fr) 1998-11-13 1998-11-13 Emulsion de type aqueux contenant un compose d'acide ascorbique
JP2000582008A JP2003502275A (ja) 1998-11-13 1998-11-13 アスコルビン酸化合物を含有する水中油型エマルション
EP98957932A EP1128805A1 (fr) 1998-11-13 1998-11-13 Emulsion de type aqueux contenant un compose d'acide ascorbique
CN98814310A CN1356888A (zh) 1998-11-13 1998-11-13 含有抗坏血酸化合物的水包油乳液

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/US1998/024255 WO2000028960A1 (fr) 1998-11-13 1998-11-13 Emulsion de type aqueux contenant un compose d'acide ascorbique

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WO2000028960A1 true WO2000028960A1 (fr) 2000-05-25

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JP (1) JP2003502275A (fr)
KR (1) KR20010107964A (fr)
CN (1) CN1356888A (fr)
AU (1) AU1407199A (fr)
BR (1) BR9816071A (fr)
CA (1) CA2350407A1 (fr)
CZ (1) CZ20011527A3 (fr)
WO (1) WO2000028960A1 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2022129403A1 (fr) * 2020-12-18 2022-06-23 L'oreal Composition comprenant des gélifiants aqueux, des tensioactifs et de l'acide ascorbique
WO2022167197A1 (fr) * 2021-02-02 2022-08-11 Beiersdorf Ag Produit cosmétique contenant du dioxyde de titane en phase aqueuse

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20120113765A (ko) * 2007-01-16 2012-10-15 더 프록터 앤드 갬블 캄파니 화장 조성물

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0487404A1 (fr) * 1990-11-19 1992-05-27 Kabushiki Kaisha Hayashibara Seibutsu Kagaku Kenkyujo Composition dermatologique externe
GB2259014A (en) * 1991-08-23 1993-03-03 Fischer Pharma Ltd Compositions containing flavonoids
EP0669126A1 (fr) * 1994-01-31 1995-08-30 L'oreal Emulsion stabilisée, destinée à hydrater la peau et son utilisation
WO1998034591A1 (fr) * 1997-02-11 1998-08-13 The Procter & Gamble Company Compositions pour reduire l'hyperpigmentation de la peau

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0487404A1 (fr) * 1990-11-19 1992-05-27 Kabushiki Kaisha Hayashibara Seibutsu Kagaku Kenkyujo Composition dermatologique externe
GB2259014A (en) * 1991-08-23 1993-03-03 Fischer Pharma Ltd Compositions containing flavonoids
EP0669126A1 (fr) * 1994-01-31 1995-08-30 L'oreal Emulsion stabilisée, destinée à hydrater la peau et son utilisation
WO1998034591A1 (fr) * 1997-02-11 1998-08-13 The Procter & Gamble Company Compositions pour reduire l'hyperpigmentation de la peau

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2022129403A1 (fr) * 2020-12-18 2022-06-23 L'oreal Composition comprenant des gélifiants aqueux, des tensioactifs et de l'acide ascorbique
FR3117847A1 (fr) * 2020-12-18 2022-06-24 L'oreal Composition comprenant des gélifiants aqueux, des tensioactifs et de l’acide ascorbique
WO2022167197A1 (fr) * 2021-02-02 2022-08-11 Beiersdorf Ag Produit cosmétique contenant du dioxyde de titane en phase aqueuse

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JP2003502275A (ja) 2003-01-21
KR20010107964A (ko) 2001-12-07
CN1356888A (zh) 2002-07-03
BR9816071A (pt) 2001-08-14
EP1128805A1 (fr) 2001-09-05
CA2350407A1 (fr) 2000-05-25
AU1407199A (en) 2000-06-05
CZ20011527A3 (cs) 2001-10-17

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