WO2008073684A1 - Composition pour traiter le vieillissement de la peau comprenant un acide hydroxycinnamique tel que l'acide p-coumarique - Google Patents

Composition pour traiter le vieillissement de la peau comprenant un acide hydroxycinnamique tel que l'acide p-coumarique Download PDF

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WO2008073684A1
WO2008073684A1 PCT/US2007/085193 US2007085193W WO2008073684A1 WO 2008073684 A1 WO2008073684 A1 WO 2008073684A1 US 2007085193 W US2007085193 W US 2007085193W WO 2008073684 A1 WO2008073684 A1 WO 2008073684A1
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Prior art keywords
skin
acid
glycol
peg
mixtures
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PCT/US2007/085193
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English (en)
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Nava Dayan
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Lipo Chemicals Inc.
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Publication of WO2008073684A1 publication Critical patent/WO2008073684A1/fr

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    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
    • A61K31/19—Carboxylic acids, e.g. valproic acid
    • A61K31/194—Carboxylic acids, e.g. valproic acid having two or more carboxyl groups, e.g. succinic, maleic or phthalic acid
    • 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
    • A61K8/36—Carboxylic acids; Salts or anhydrides thereof
    • A61K8/365—Hydroxycarboxylic acids; Ketocarboxylic acids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/16—Emollients or protectives, e.g. against radiation
    • 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
    • A61Q19/007—Preparations for dry 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/52—Stabilizers
    • A61K2800/522—Antioxidants; Radical scavengers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q1/00—Make-up preparations; Body powders; Preparations for removing make-up
    • A61Q1/02—Preparations containing skin colorants, e.g. pigments
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • 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
    • A61Q19/10—Washing or bathing preparations

Definitions

  • the present invention relates to cosmetic and dermatological compositions that treat aging skin. More particularly, the present invention relates to compositions having an enhanced ability to improve the appearance and condition of aging mammalian skin, for example, by reducing skin imperfections, such as wrinkles, and by improving skin properties, such as tone and elasticity. Photoaging also leads to undesired pigmentation (age spots) and uneven skin tone.
  • the compositions comprise a hydroxycinnamic acid or a methoxycinnamic acid in a suitable carrier for topical application to mammalian skin.
  • hydroxycinnamic acid or methoxycinnamic acid can be incorporated into various cosmetic formulations, for example, skin lotions, creams, body rinses, bath gels, skin-cleansing agents, skin-coloring compositions, foundation liquids and powders (compressed or loose), topical medicaments, and skin-treatment products.
  • Natural-looking skin is influenced by a number of physiological and genetic factors. Years of exposure to environmental insults lead to an accumulated damage of the skin, and the ability of the skin to repair itself after exposure to an insult decreases with age.
  • Standard definitions of an ideal, youthful skin include skin having a transparent quality with uniform undertones of color (e.g., rosy-red cheeks). The basis of this natural- looking appearance is the skin structure itself.
  • the outer layer of human skin is a semitransparent layer termed the stratum corneum. The transparency of the stratum corneum permits observation of the deeper layers of skin, where blood vessels and pigments reside.
  • an ideal skin also should be smooth and even, with no apparent surface flaws. Very few individuals meet the ideal skin standard, therefore most individuals seek, and in some cases require, assistance in the form of cosmetic compositions. Thus, a wide variety of "makeup" compositions have been developed to improve skin appearance.
  • Skin care, and particularly antiaging strategies is a substantial and growing industry encompassing cosmetic, pharmaceutical, and physical therapy disciplines. As the population ages and wishes to maintain a youthful vigor and appearance, employing antiaging strategies is an option for an individual to retain the appearance of youth. A large portion of this antiaging strategy is skin treatment, which is the most visible indicia of aging. As a result, consumer attention is constantly focused on the newest compositions and methods to defy the effects of skin aging, counteract wrinkles, smooth the skin, brighten the skin, and provide additional antiaging benefits.
  • compositions capable of maintaining or restoring a youthful appearance in aging skin and/or improving the condition and appearance of aging skin.
  • the composition and method of the present invention meet this need by effectively maintaining and/or improving skin tone and elasticity, thereby reducing the incidence of wrinkles in human skin, via a topical application of the composition.
  • the present invention is directed to a cosmetic or dermato logical composition used in a method of treating aging skin. More particularly, the present invention is directed to a composition that demonstrates an enhanced ability to maintain a youthful skin appearance and condition, and to improve the appearance and condition of aging skin. The compositions maintain and improve skin tone and elasticity, and reduce the incidence of skin imperfections, such as sags and wrinkles.
  • a hydroxycinnamic acid or a methoxycinnamic acid i.e., collectively termed an HCA
  • the HCA is dissolved in an organic compound having one or more hydroxy groups, a silicone fluid, or a mixture thereof.
  • the organic compound having a hydroxy group can be an organic solvent or a surfactant, e.g., a polyethylene glycol (PEG) or a monoC 1-4 alkyl ether of an ethylene glycol oligomer or a propylene glycol oligomer.
  • one embodiment of the present invention is to provide a method of treating aging mammalian skin comprising a step of contacting the skin of a mammal in need of such treatment with a sufficient amount of a hydroxycinnamic acid, a methoxycinnamic acid, or mixtures thereof, to maintain or improve at least visible indicia of aging.
  • Another embodiment of the present invention is to provide a composition
  • a composition comprising about 0.01% to about 30%, by weight, of an HCA, preferably dissolved in a solvent that enhances delivery to and availability of an HCA at an active skin site.
  • solvents include, but are not limited to, an organic compound having one or more hydroxy group, a silicone fluid, or a mixture thereof.
  • the composition is applied directly to the skin, and is in the form of a cosmetic or dermatological formulation, for example, an oil-in- water emulsion, a water-in-oil emulsion, or a gel.
  • Another embodiment of the present invention is to provide a method of treating aging mammalian skin, including humans, comprising applying a composition comprising an HCA, preferably dissolved in an organic compound having one or more hydroxy group, a silicone fluid, or a mixture thereof, to a skin surface of a mammal in need of such treatment.
  • the method is capable of improving visible indicia of aging skin, e.g. reducing wrinkles, removing age spots, or maintaining a youthful skin appearance and condition.
  • the HCA is incorporated into a composition suitable for application to the skin of a mammal.
  • the composition can further contain additional formulation ingredients for an efficient and efficacious application of the HCA to the skin.
  • Another embodiment of the present invention is to provide a method of treating skin, and particularly aging skin, comprising a topical application to the skin of a composition containing an HCA having skin-beneficial properties, including maintaining a healthy skin and reducing signs of skin aging.
  • the composition and method also provide anti-wrinkle properties and antioxidant properties.
  • Still another embodiment of the present invention is to provide a method of treating aging skin comprising a topical application of an HCA having skin-beneficial properties at least one time per 24-hour period, and/or in accordance with a treatment regimen of at least four weeks in duration.
  • the topically applied compositions include skin lotions, creams, body rinses, skin- cleansing agents, skin-coloring compositions, foundation liquids and powders (compressed or loose), topical medicaments, and skin-treatment products.
  • Yet another embodiment of the present invention is to provide a composition containing an HCA dissolved in an organic compound having one or more hydroxy group and/or a silicone fluid, and use of the composition as a skin-care product, a topical drug product, or a cosmetic product to treat visual indicia of aging skin.
  • Fig. 1 contains plots of reduction in skin tryptophan levels by application of p-HCA, MAP, or HQ to the skin of Asian women for 2 to 8 weeks;
  • Fig. 2 contains bar graphs showing the % reduction in skin tryptophan levels in skin after treatment with an emulsion containing p-HCA, MAP, or HQ for 6 to 8 weeks;
  • Fig. 3 contains graphs showing the reduction of pepsin digestible collagen crosslinks on skin treated with a composition containing p-HCA, MAP, or HQ for 4 to 8 weeks;
  • Fig. 4 contains bar graphs showing the % reduction in pepsin digestible collagen crosslinks after treatment with a composition containing p-HCA, MAP, or HQ for 6 to 8 weeks.
  • a reduction in the visual indicia of skin aging occupies greater consumer emphasis today than ever before.
  • the incorporation of botanical antioxidants in cosmetic products is gaining popularity attributed to their antiaging, wrinkle reduction, and other skin tone benefits.
  • Cosmetic products containing known antioxidants e.g., vitamin E, Coenzyme QlO, ascorbic acid, alpha-lipoic acid, and soy isoflavones, are available commercially.
  • the design of a topical antioxidant composition offers challenges, particularly because many antioxidants have a limited stability.
  • compositions of the present invention maintain and improve the appearance and condition of the skin and reduce the effects of aging on skin, such as wrinkles and other visual indicia of skin aging, like a loss of skin tone and elasticity.
  • the present cosmetic compositions reduce the appearance of wrinkles and fine lines, particularly, but not limited to, on the face area.
  • the present invention is directed to providing compositions that overcome problems associated with prior compositions used to treat aging skin.
  • the present compositions contain an HCA and maintain and improve skin tone and elasticity.
  • the term “maintains” means that a visual indicia of skin aging does not change over time, e.g., the incidence of wrinkles, sagging, skin tone, elasticity, and/or indicia of skin aging does not increase over time, but rather remains relatively constant.
  • the term “improves” means that a visual indicia of skin aging is ameliorated, palliated, or reversed after treatment in accordance with the present invention.
  • Signs of skin aging treated by the present composition and method include, but are not limited to, all visible and tactile indicia, as well as any other macro or micro effects caused by intrinsic factors or extrinsic factors, e.g., chronological aging and/or environmental damage.
  • Aging signs can result from processes that include, but are not limited to, the development of textural discontinuities, such as wrinkles and coarse deep wrinkles, skin lines, crevices, bumps, large pores (e.g., associated with adrenal structures, such as sweat gland ducts, sebaceous glands, or hair follicles) or unevenness or roughness, loss of skin elasticity (e.g., loss and/or inactivation of functional skin elastin), sagging (including loss and/or damage to functional subcutaneous muscle tissue and including puffmess in the eye area and jowls), loss of skin firmness, loss of skin tightness, loss of skin recoil from deformation, discoloration (including under eye circles), blotching, shallowness, and other histological changes in the stratum corneum, dermis, epidermis, the skin vascular system (e.g., telangiectasia or spider vessels), and underlying tissues, especially those proximate to the skin.
  • textural discontinuities such as wrinkle
  • crosslinked collagen levels are known to increase with age.
  • crosslinked collagen levels are significantly reduced by treatment with an HCA.
  • an 8-week study conducted on an Asian panel compared the effects of hydroquinone, magnesium ascorbyl phosphate (MAP), and hydroxycinnamic acid (HCA) on tryptophan and crosslinked collagen levels.
  • HCA a radical scavenger and a tyrosinase inhibitor, was superior to both hydroquinone and MAP in reducing tryptophan and crosslinked collagen levels.
  • HCA therefore is unique in its simultaneous activity of improving skin condition by reversing signs of aging both in terms of skin tone and elasticity.
  • p-hydroxycinnamic acid is a phenolic cinnamic acid derivative that inhibits the development of cancer, and is found in various plants such as tomatoes, green peppers, carrots, strawberries, and pineapples, as well as herbal plants, like basil and turmeric.
  • HCAs are nontoxic and nonirritating and are potent tyrosinase inhibitors.
  • Some HCAs, like p-hydroxycinnamic acid (p-HCA) can be found in fruits and vegetables, and presently are being used in the food industry as antioxidants.
  • p-Hydroxycinnamic acid is activated during digestion and interferes with the development of cancer-causing nitrosamines.
  • p-Hydroxycinnamic acid also is used in the cosmetic industry as a bacteriostat.
  • HCAs have poor skin permeability.
  • HCAs are highly insoluble in solvents and carriers typically used in skin care and dermatological compositions.
  • a preferred embodiment of the present invention incorporates an HCA into a cosmetic composition and permits the use of an HCA in treating aging skin.
  • compositions and methods of the present invention are useful in treating a variety of conditions related to aging skin, for example, wrinkles, fine lines, poor skin tone, and loss of elasticity.
  • the present invention is directed to a method of treating skin comprising topically applying a composition comprising an HCA dissolved in a silicone fluid or a hydroxy-containing compound, e.g., a PEG or a monoC 1-4 alkyl ether of an ethylene glycol oligomer or a propylene glycol oligomer, to skin to help maintain a youthful skin appearance or improve the appearance and condition of aging skin.
  • a hydroxy-containing compound e.g., a PEG or a monoC 1-4 alkyl ether of an ethylene glycol oligomer or a propylene glycol oligomer
  • An active agent in a present composition and method is an HCA.
  • an HCA is dissolved in an organic compound having one or more hydroxy group, a silicone fluid, or a mixture thereof.
  • the organic compound containing one or more hydroxy group can be a surfactant or an organic solvent.
  • the compound containing one or more hydroxy group can contain one to six hydroxy groups, and typically contains one to three hydroxy groups.
  • the HCA also can be dissolved or dispersed in other solvents and surfactants typically used in cosmetic and dermato logic compositions.
  • the HCA is dissolved in a monoCi -4 alkyl ether of an ethylene glycol oligomer or a propylene glycol oligomer, also termed herein as a "monoQ ⁇ alkyl ether.”
  • the HCA is dissolved in a C 2 -C 4 alcohol, a C 3 -C 5 glycol, a polyethylene glycol (e.g., PEG-4), a polypropylene glycol, a triol, a polyol, an ethoxylated glycerin, an ethylene oxide-propylene oxide block copolymer, or mixtures thereof.
  • Nonlimiting examples of useful compounds include propylene glycol, butylene glycol, pentylene glycol, glycereth-7 through glycereth-31, PEG-4 through PEG-800, PPG-3 through PPG-69, ethanol, isopropyl alcohol, n-propanol, n-butanol, sec-butanol, t-butyl alcohol, diethylene glycol, triethylene glycol, dipropylene glycol, tripropylene glycol, hexylene glycol, 1 ,2,6-hexanetriol, sorbitol, and mixtures thereof.
  • Examples of preferred compounds having one or more hydroxy group include, but are not limited to, ethoxydiglycol, diethylene glycol, triethylene glycol, dipropylene glycol, tripropylene glycol, PEG-4 through PEG-20, PPG-3 through PPG- 15, an ethylene oxide- propylene oxide block copolymer containing about 4 to about 20 total ethylene oxide and propylene oxide units.
  • Nonlimiting examples include PEG-4, PEG-6, PEG-8, PEG-9, PEG-10, PEG-12, PEG-16, PEG-18, PEG-20, PPG-3, PPG-9, PPG-12, PPG-15, poloxamear 101, and mixtures thereof.
  • Useful surfactants having one or more hydroxy groups include nonionic surfactants, not limited to, ethoxylated octyl phenols, ethoxylated nonyl phenols, ethoxylated linear C 8 - C 22 alcohols, propoxylated linear C 8 -C 22 alcohols, ethoxylated and propoxylated C 8 -C 22 alcohols, polyethylene glycol ethers of sorbitol, or mixtures thereof.
  • Useful silicone fluids include linear and cyclic, volatile and nonvolatile, dimethyl siloxane fluids, including siloxane fluids having phenyl substituents.
  • Useful silicone fluids are disclosed in U.S. Patent No. 5,456,863, incorporated herein by reference.
  • a composition utilized in the present invention contains about 0.01% to about 30%, by weight, of an HCA.
  • the composition can be used as is, diluted, or admixed with other composition ingredients known in the cosmetic and dermatologic arts to provide an efficacious and esthetic composition for topical application to the skin.
  • the HCA can be, but is not limited to, 2-, 3-, or 4-hydroxycinnamic acids; 2,3-, 2,4- , or 3-4-dihydroxycinnamic acid; 2-, 3-, or 4-methoxycinnamic acid; 3-hydroxy-4- methoxycinnamic acid; 4-hydroxy-3-methoxycinnamic acid; or mixtures thereof.
  • the HCA comprises 2-, 3-, or 4-hydroxycinnamic acid.
  • An especially useful HCA is 4-hydroxycinnamic acid.
  • p-HCA 4- hydroxycinnamic acid
  • p-HCA 4- hydroxycinnamic acid
  • p-HCA 4- hydroxycinnamic acid
  • p-HCA 4- hydroxycinnamic acid
  • p-HCA 4- hydroxycinnamic acid
  • p-HCA 4- hydroxycinnamic acid
  • p-HCA 4- hydroxycinnamic acid
  • p-HCA 4- hydroxycinnamic acid
  • p-HCA 4- hydroxycinnamic acid
  • HCA solution or dispersion can be applied directly to skin.
  • the amount of HCA in the solution or dispersion typically is about 0.01% to about 10%, by weight of the solution or dispersion.
  • the HCA solution or dispersion also can be diluted with a solvent or other carrier prior to application to the skin.
  • the diluting solvent can be the same or different from the organic compound used to dissolve or disperse the HCA.
  • the HCA is stabilized to permit penetration of the skin surface and treating of the skin, and particularly aging skin.
  • the HCA solution or dispersion can be formulated into various product forms, such as emulsions or gels, by the addition of formulation ingredients to the HCA, or addition of the HCA to the formulation ingredients.
  • formulation ingredients and product forms are discussed below, and do not adversely affect the ability of the HCA to treat aging skin.
  • the topical, cosmetic or pharmaceutical compositions can be in any convenient form, such as a clear liquid, lotion, cream, gel, mask, spray, cleanser, or shower gel.
  • the HCA solution or dispersion also can be added to already formulated products.
  • the HCA solution or dispersion can be added to a skin lotion that has already been made to provide added benefits from such lotion product.
  • HCA is dissolved in an organic compound having one or more hydroxy group and/or a silicone fluid, like a PEG or a monoC 1-4 alkyl ether of an ethylene glycol oligomer or a propylene glycol oligomer.
  • a silicone fluid like a PEG or a monoC 1-4 alkyl ether of an ethylene glycol oligomer or a propylene glycol oligomer.
  • dissolving the HCA in a suitable hydroxy-containing compound improves penetration of the HCA through the skin surface and facilitates the treatment of aging skin, which provides a degree of antiaging effects that previously could not be attained.
  • a monoCi -4 alkyl ether of an ethylene glycol oligomer or a propylene glycol oligomer used to dissolve HCA has a general formula:
  • R 1 is Ci ⁇ alkyl
  • R 2 is hydrogen or methyl
  • n is 2 or 3.
  • R 1 is methyl, ethyl, isopropyl, n-propyl, n-butyl, sec-butyl, isobutyl, or tert-butyl.
  • Nonlimiting examples of a monoCi -4 alkyl ether of an ethylene glycol or propylene glycol oligomer include, but are not limited to, ethoxydiglycol, methoxydiglycol, butoxydiglycol, methoxytriglycol, ethoxytriglycol, and mixtures thereof.
  • Preferred monoethers include ethoxydiglycol and methoxydiglycol.
  • the monoether comprises ethoxydiglycol.
  • the organic compound having one or more hydroxy group comprises diethylene glycol, triethylene glycol, dipropylene glycol, tripropylene glycol, PEG-4 through PEG-20, PPG-3 through PPG-15, an ethylene oxide- propylene oxide block copolymer containing about 4 to about 20 total ethylene oxide and propylene oxide units, and mixtures thereof.
  • an HCA solution or dispersion can be applied as is, after dilution, or after incorporation into a cosmetic or dermatological formulation.
  • the final composition also can contain an optional second active antiaging agent.
  • second active antiaging agents include, but are not limited to, skin exfoliants; a steroidal antiinflammatory agent of the hydrocortisone-type and the like; a nonsteroidal antiinflammatory agent selected from the group consisting of acetylsalicylic acid, acetaminophen, naproxen, and fenamic acid derivatives, such as the sodium salt; antiinflammatory agents, such as alpha-bisabolol, beta- glycyrrhetinic acid, allantoin, aloe extract, rosmarinic acid, azulene or a derivative thereof, asiaticoside, sericoside, ruscogenin, escin, escolin, quercetin, rutin, betulinic acid or a derivative thereof, catechin or a
  • compositions and methods of the present invention are useful for treating the hair and nails to impart antiaging benefits.
  • An HCA-containing composition is useful in personal care, cosmetic, and pharmaceutical compositions.
  • the compositions provide an effective delivery of an HCA to treat the skin and impart antiaging effects, such as improved skin tone and elasticity and a reduction in wrinkles and fine lines.
  • the resulting compositions for treating skin can be formulated with other topically-applied active compounds, in addition to or in lieu of an optional second active antiaging agent to achieve both antiaging effects and a second cosmetic or therapeutic effect different from antiaging.
  • a topically- applied compound for providing a second cosmetic or therapeutic effect can be any of a wide variety of compounds, either water soluble or oil soluble.
  • Additional topically-applied active compounds such as hormones, analgesics, anesthetics, sun screens, skin whiteners, antiacne agents, antibacterial agents, antifungal agents, botanical extracts, pharmaceuticals, minerals, plant extracts, concentrates of plant extracts, exfoliants, emollients, moisturizers, skin protectants, humectants, silicones, skin soothing ingredients, colorants, perfumes, and like can be added to the composition.
  • the quantities of such active compounds present in the composition are sufficient to perform their intended function, without adversely affecting the antiaging benefits of the composition.
  • such a topically applied active compound can be one of, or a mixture of, a cosmetic compound, a medicinally active compound, a compound used in cosmetics or personal care, or any other compound that is useful upon topical application to the skin.
  • topically active agents include, but are not limited to, skin-care compounds, plant extracts, antioxidants, insect repellants, counterirritants, vitamins, steroids, antibacterial compounds, antifungal compounds, antiinflammatory compounds, topical anesthetics, sunscreens, optical brighteners, and other cosmetic and medicinal topically effective compounds.
  • a skin conditioner can be the topically applied compound.
  • Skin conditioning agents include, but are not limited to, humectants, such a fructose, glucose, glycerin, propylene glycol, glycereth-26, mannitol, pyrrolidone carboxylic acid, hydrolyzed lecithin, coco-betaine, cysteine hydrochloride, glucamine, sodium gluconate, potassium aspartate, oleyl betaine, thiamine hydrochloride, sodium laureth sulfate, sodium hyaluronate, hydrolyzed proteins, hydrolyzed keratin, amino acids, amine oxides, water-soluble derivatives of vitamins A, E, and D, selenium and derivatives thereof, amino-functional silicones, ethoxylated glycerin, alpha-hydroxy acids and salts thereof, fatty oil derivatives, such as PEG-24 hydrogenated lanolin, beta-hydroxy acids and salts thereof, fatty oil
  • CTFA Cosmetic Ingredient Handbook First Ed., J. Nikotakis, ed., The Cosmetic, Toiletry and Fragrance Association (1988), (hereafter CTFA Handbook), pages 79- 84, incorporated herein by reference.
  • the skin conditioner also can be a water-insoluble ester having at least 10 carbon atoms, and preferably 10 to about 32 carbon atoms.
  • Suitable esters include those comprising an aliphatic alcohol having about eight to about twenty carbon atoms and an aliphatic or aromatic carboxylic acid including from two to about twelve carbon atoms, or conversely, an aliphatic alcohol having two to about twelve carbon atoms with an aliphatic or aromatic carboxylic acid including about eight to about twenty carbon atoms.
  • the ester is either straight-chained or branched. Suitable esters, therefore, include, for example, but are not limited to:
  • aliphatic polyhydric alcohol esters including, but not limited to: propylene glycol dipelargonate;
  • aliphatic esters of aromatic acids including, but not limited to: C] 2 -C 15 alcohol esters of benzoic acid, octyl salicylate, sucrose benzoate, and dioctyl phthalate.
  • the topically applied compound also can be retinoic acid or a retinol derivative.
  • the topically applied compound further can be an antioxidant or an optical brightener, like a distyrylbiphenyl derivative, stilbene or a stilbene derivative, a pyralozine derivative, or a coumarin derivative.
  • Optical brighteners useful as the topically applied compound can be any compound capable of absorbing an invisible UV portion of the daylight spectrum, and converting this energy into the longer visible wavelength portion of the spectrum.
  • the optical brightener is colorless on the substrate, and does not absorb energy in the visible part of the spectrum.
  • the optical brightener typically is a derivative of stilbene or 4,4'-diaminostilbene, biphenyl, a 5-membered heterocycle, e.g., triazole, oxazole, or imidazole, or a 6-membered heterocycle, e.g., a coumarin, a naphthalamide, or an s-triazine.
  • optical brighteners are available under a variety of tradenames, such as TINOP AL ® , LEUCOPHOR ® , and CALCOFLUOR ® .
  • Specific fluorescent compounds include, but are not limited to, TINOP AL ® 5BM, CALCOFLUOR ® CG, and LEUCOPHOR ® BSB.
  • sunscreen compounds such as benzophenone-3, tannic acid, uric acids, quinine salts, dihydroxy naphtholic acid, an anthranilate, p-aminobenzoic acid, phenylbenzimidazole sulfonic acid, PEG-25, or p-aminobenzoic acid can be used as the topically applied compound.
  • sunscreen compounds such as dioxybenzone, ethyl 4- [bis(hydroxypropyl)] aminobenzoate, glyceryl aminobenzoate, homosalate, methyl anthranilate, octocrylene, octyl methoxycinnamate, octyl salicylate, oxybenzone, padimate O, red petrolatum, titanium dioxide, 4-menthylbenzylidene camphor, benzophenone-1, benzophenone-2, benzophenone-6, benzophenone-12, isopropyl dibenzoyl methane, butyl methoxydibenzoylmethane, zotocrylene, or zinc oxide can be used as the topically applied compound.
  • Other sunscreen compounds are listed in CTFA Handbook, pages 86 and 87, incorporated herein by reference.
  • topically applied drugs like antifungal compounds, antibacterial compounds, antiinflammatory compounds, topical anesthetics, skin rash, skin disease, and dermatitis medications, and antiitch and irritation-reducing compounds can be used as the active agent in the compositions of the present invention.
  • analgesics such as benzocaine, dyclonine hydrochloride, aloe vera, and the like; anesthetics such as butamben picrate, lidocaine hydrochloride, xylocaine, and the like; antibacterials and antiseptics, such as povidone-iodine, polymyxin b sulfate-bacitracin, zinc-neomycin sulfate-hydrocortisone, chloramphenicol, ethylbenzethonium chloride, erythromycin, and the like; antiparasitics, such as lindane; essentially all dermatologicals, like acne preparations, such as benzoyl peroxide, erythromycin benzoyl peroxide, clindamycin phosphate, 5,7-dichloro-8-hydroxyquinoline, and the like; antiinflammatory agents, such as alclometasone dipropionate, betamethasone valerate, and the like;
  • topically active compound also can be a plant extract on a natural oil. Numerous plant extracts are available from Lipo Chemicals, Inc. Paterson, New Jersey.
  • Nonlimiting plant extracts are those obtained from alfalfa, aloe vera, amla fruit, angelica root, anise seed, apple, apricot, artichoke leaf, asparagus root, banana, barberry, barley sprout, bee pollen, beet leaf, bilberry fruit, birch leaf, bitter melon, black currant leaf, black pepper, black walnut, blueberry, blackberry, burdock, carrot, cayenne, celery seed, cherry, chickwood, cola nut, corn silk, cranberry, dandelion root, elderberry, eucalyptus leaf, flax oil powder, ginger root, gingko leaf, ginseng, goldenrod, goldenseal, grape, grapefruit, guava, hibiscus, juniper, kiwi, kudzu, lemon, licorice root, lime, malt, marigold, myrrh, olive leaf, orange fruit, orange peel, oregano, papaya fruit, papaya leaf, passion
  • a composition of the present invention is prepared by dissolving the HCA in an organic compound having one or more hydroxy groups, a silicone fluid, or a mixture thereof, like a monoCi -4 alkyl ether.
  • the present compositions can be admixed with other ingredients traditionally included in cosmetic, dermatological, medicinal, and other such compositions. These ingredients include, but are not limited to, dyes, fragrances, preservatives, antioxidants, detackifying agents, and similar types of compounds.
  • the ingredients are included in the composition in an amount sufficient to perform their intended function.
  • a present composition can contain a surfactant.
  • the surfactant can be an anionic surfactant, a cationic surfactant, a nonionic surfactant, or a compatible mixture of surfactants.
  • the surfactant also can be an ampholytic or amphoteric surfactant, which have anionic or cationic properties depending upon the pH of the composition.
  • anionic surfactants include, without limitation, soaps, alkyl sulfates, anionic acyl sarcosinates, methyl acyl taurates, N-acyl glutamates, acyl isethionates, alkyl phosphate esters, ethoxylated alkyl phosphate esters, alkyl sulfosuccinates, trideceth sulfates, protein condensates, mixtures of ethoxylated alkyl sulfates, and the like.
  • anionic nonsoap surfactants include, without limitation, the alkali metal salts of an organic sulfate having an alkyl radical containing about 8 to about 22 carbon atoms and a sulfonic acid or sulfuric acid ester radical.
  • zwitterionic surfactants include, without limitation, derivatives of aliphatic quaternary ammonium, phosphonium, and sulfonium compounds, in which the aliphatic radicals can be straight chain or branched and wherein one of the aliphatic substituents contains an anionic water-solubilizing group, e.g., carboxyl, sulfonate, sulfate, phosphate, or phosphonate.
  • amphoteric surfactants include, without limitation, derivatives of aliphatic secondary and tertiary amines in which the aliphatic radical can be straight chain or branched and wherein one of the aliphatic substituents contains about 8 to about 18 carbon atoms and one contains an anionic water solubilizing group, e.g., carboxyl, sulfonate, sulfate, phosphate, or phosphonate.
  • Nonionic surfactants include, without limitation, stearyldimethylbenzyl ammonium chloride; dodecyltrimethyl ammonium chloride; nonylbenzylethyldimethyl ammonium nitrate; and tetradecylpyridinium bromide.
  • Nonionic surfactants include, without limitation, compounds produced by the condensation or ethylene oxide groups with an organic hydrophobic compound, which may be aliphatic or alkyl aromatic in nature, for example, the polyethylene oxide condensates of alkyl phenols.
  • a present composition also can contain a hydrotrope.
  • a hydrotrope is a compound that has an ability to enhance the water solubility of other compounds. Specific examples of hydrotropes include, but are not limited to, sodium cumene sulfonate, ammonium cumene sulfonate, ammonium xylene sulfonate, potassium toluene sulfonate, sodium toluene sulfonate, sodium xylene sulfonate, toluene sulfonic acid, and xylene sulfonic acid.
  • hydrotropes include sodium polynaphthalene sulfonate, sodium polystyrene sulfonate, sodium methyl naphthalene sulfonate, sodium camphor sulfonate, and disodium succinate.
  • a present composition also can contain an additional organic solvent.
  • the solvent can be a water-soluble organic compound containing one to six, and typically one to three, hydroxyl groups, e.g., alcohols, diols, triols, and polyols.
  • solvents include, but are not limited to, methanol, ethanol, isopropyl alcohol, n-butanol, n-propyl alcohol, ethylene glycol, propylene glycol, glycerol, diethylene glycol, dipropylene glycol, tripropylene glycol, hexylene glycol, butylene glycol, 1,2,6-hexanetriol, sorbitol, PEG-4, 1,5- pentanediol, similar hydroxyl-containing compounds, and mixtures thereof.
  • the solvent also can be water or an aprotic solvent, e.g., dimethyl sulfoxide or tetrahydrofuran.
  • a present composition also can contain a thickening or gelling agent.
  • a thickening or gelling agent can be, for example, a polymer that is water soluble or that generates a colloidal solution in water.
  • a thickening or gelling agent therefore, can be, for example, polymers or copolymers unsaturated carboxylic acids or unsaturated esters, polysaccharide derivatives, gums, colloidal silicates, polyethylene glycols (PEG) and their derivatives, polyvinylpyrrolidones and their derivatives, polyacrylamides and their derivatives, polyacrylonitriles, hydrophilic silica gels, or mixtures thereof.
  • Specific thickening or gelling agents can be, for example, acrylic and/or methacrylic polymers or copolymers, vinylcarboxylic polymers, polyglyceryl acrylates or methacrylates, polyacrylamides derivatives, cellulose or starch derivatives, chitin derivatives, alginates, amino acids, ceramides, fatty acids, cholesterol and derivatives thereof, and other natural moisturizing compounds, hyaluronic acid and its salts, chonodroitin sulphates, xanthan, gellan, Rhamsan, karaya or guar gum, carob flour, and colloidal aluminum magnesium silicates of the montmorillonite type.
  • acrylic and/or methacrylic polymers or copolymers vinylcarboxylic polymers, polyglyceryl acrylates or methacrylates, polyacrylamides derivatives, cellulose or starch derivatives, chitin derivatives, alginates, amino acids, ceramides, fatty acids, cholesterol and derivatives thereof, and
  • Additional thickening or gelling agents include vinylcarboxylic polymers sold under the tradename CARBOPOL ® (Goodrich), acrylic acid/ethyl acrylate copolymers, acrylic acid/stearyl methacrylate copolymers, carboxymethylcellulose, hydroxymethylcellulose, hydroxypropylcellulose, microcrystalline cellulose, hydroxypropyl guar, colloidal hectorites, bentonites, and the like.
  • optional ingredients included in a present composition can be, but not limited to, pH adjusters, chelating agents, preservatives, buffering agents, foam stabilizers, opacifiers, and similar classes of ingredients known to persons skilled in the art.
  • Specific optional ingredients include inorganic phosphates, sulfates, and carbonates as buffering agents; EDTA and phosphates as chelating agents; and acids and bases as pH adjusters.
  • Nonlimiting examples of basic pH adjusters are ammonia; mono-, di-, and tri-alkyl amines; mono-, di-, and tri-alkanolamines; alkali metal and alkaline earth metal hydroxides; and mixtures thereof.
  • Specific, nonlimiting examples of basic pH adjusters are ammonia; sodium, potassium, and lithium hydroxide; monoethanolamine; triethylamine; isopropanolamine; diethanolamine; and triethanolamine.
  • Examples of acidic pH adjusters are the mineral acids and organic carboxylic acids.
  • mineral acids are citric acid, hydrochloric acid, nitric acid, phosphoric acid, and sulfuric acid.
  • the HCA can be incorporated into compositions designed as cosmetic basecoats and undercoats, bath capsules, bath oils, bath tablets, bath salts, bath soaps, blushers, face, body, and hand creams and lotions, cosmetic foundations, hormone creams and lotions, leg and body paints, makeup bases, makeup fixatives, makeup products, moisturizing creams and lotions, night creams and lotions, paste masks, skin care products, skin fresheners, skin lighteners, tonics, dressings, and wrinkle smoothing creams and lotions.
  • compositions designed as cosmetic basecoats and undercoats bath capsules, bath oils, bath tablets, bath salts, bath soaps, blushers, face, body, and hand creams and lotions, cosmetic foundations, hormone creams and lotions, leg and body paints, makeup bases, makeup fixatives, makeup products, moisturizing creams and lotions, night creams and lotions, paste masks, skin care products, skin fresheners, skin lighteners, tonics, dressings, and wrinkle smoothing cream
  • the HCA can be incorporated into lotions; makeup preparations, like makeup foundations; skin care preparations, like hand lotions, vanishing creams, night creams, sunscreens, body lotions, facial creams, clay masks, moisturizing lotions, makeup removers, antiacne preparations, antiaging preparations, and sebum control; analgesic and cortisonal steroid creams and preparations; insect repellants; and facial masks and revitalizers.
  • the compositions also can be incorporated into plasters, bandages, dressings, gauze pads, and similar articles.
  • the final composition can be in the form of a solution, an oil-in- water emulsion, a water-in-oil emulsion, a gel, a microemulsion, a nanoemulsion, or other product form known in the skin care and dermatological arts.
  • the HCA also can be delivered from an encapsulated or nonencapsulated delivery system, a liposome, or other vesicle or lamellar delivery system.
  • the composition form can be, for example, a liquid form, e.g., a solution, a gelled solution, or a suspension in an aqueous or oily medium; or a semi-liquid formulation, e.g., a cream, a gel, a paste, an ointment, a salve, a liposome, an emulsion, or a microemulsion.
  • a liquid form e.g., a solution, a gelled solution, or a suspension in an aqueous or oily medium
  • a semi-liquid formulation e.g., a cream, a gel, a paste, an ointment, a salve, a liposome, an emulsion, or a microemulsion.
  • a composition of the present invention is topically applied to the skin as needed in order to impart antiaging properties to the skin to a desired degree.
  • the composition is topically applied to the skin one to four times per day.
  • application of a present composition can be more or less frequent as prescribed, required, or desired.
  • the present compositions are applied to the skin by spraying or rubbing.
  • the preferred route of administration is rubbing onto the skin with a soft massage to ensure intimate contact with the skin and full absorption by the skin.
  • the flow rate was 1 ml/min and the wavelength for detection was 270 nm.
  • p-HCA had a relatively high solubility in PEG-4 and ethoxydiglycol at 25°C of 18.5% and 19.7%, by weight, respectively. It was further found that p-HCA had a relatively high solubility in PEG-2 (diethylene glycol), PEG-6, and PEG-8 at 25°C of 18.1%, 19.7%, and 19.7%, by weight, respectfully.
  • hydroethanolic solutions/gels e.g., 30% hydroethanolic solution: 0.75%; ethanol: 14.8%; pentylene glycol: 1.75%; butylene glycol: 2.25%; glycereth-26: 7%; silicone fluid DC 193: 4.7%.
  • the skin care emulsion to which solid p-HCA or the p-HCA solution was added had the following formula (w/w%): 85.35 water, 0.20 methylparaben, 0.35 xanthan gum, 5.0 butylene glycol, 4.0 sesame oil, 2.50 glyceryl stearate, 0.50 PEG-150 distearate, 1.25 neopentyl glycol, dicaprylate/dicaprate, 0.60 emulsifying wax, 0.25 imidazolidinyl urea. [0088] The skin care emulsions containing p-HCA were applied to cadaver skin.
  • the receptor contained an isotonic phosphate buffer with 30% ethanol, and was stirred continuously at 600 rpm.
  • Samples of dermatomed human cadaver skin (NDRA, Philadelphia) were placed on the cells and prehydrated for 1 hour prior to the experiment.
  • One milliliter of each formulation was added to the donor compartment of each cell, which was covered tightly with PARAFILM ® .
  • Samples (300 ⁇ l) were withdrawn from the receptor compartment every hour over 8 hours, and replaced with 300 ⁇ l of fresh receptor solution. After 8 hours, the skin was removed and cut into small pieces.
  • the skin pieces were homogenized using a Kinematica POLYTRON ® homogenizer and centrifuged. The supernatant was filtered through 0.22 ⁇ filters, and the p-HCA content was quantified.
  • the cumulative amount of p-HCA ( ⁇ g/cm 2 of skin) at the end of 8 hours was 38.10 ⁇ 3.43.
  • the exposed area of the skin was 0.636 cm 2 , therefore the cumulative amount of p-HCA in micrograms in the receptor at the end of 8 hours was 25.54 ⁇ g. It also was determined that the average skin content of p-HCA was 78.68 ⁇ g.
  • the cumulative amount of p-HCA ( ⁇ g/cm 2 of skin) at the end of 8 hours was 58.80 ⁇ 11.3.
  • the exposed area of the skin was 0.636 cm 2 , therefore the cumulative amount of p-HCA in micrograms in the receptor at the end of 8 hours was 37.39 ⁇ g. It also was determined that the average skin content of p-HCA was 87.27 ⁇ g.
  • the method used to determine skin permeability was the Franz diffusion method disclosed above.
  • the test results showed that the above formula deposited an amount of HCA in the skin that is four times greater than the amount transmitted through the skin, which demonstrates a targeted delivery of p-HCA to the site of melanin formation.
  • 3.9 mcg/ml of p-HCA was found in the receptor compartment of the skin (i.e., permeated through the skin) as opposed to 16.3 mcg/ml p-HCA found within the skin.
  • Asian females aged 39-51, were treated either with (a) a present composition containing 0.9% (by weight) p-HCA and PEG-4; (b) a 1% (by weight) magnesium ascorbyl phosphate (MAP) composition, or (c) a 2% (by weight) hydroquinone (HQ) composition, over a period of eight weeks, applied twice daily on the inner forearm. Tryptophan and crosslinked collagen were measured over time, and calculated as a percent reduction in peak height (treated skin vs. untreated skin). No skin irritation was observed after applying a present composition to skin, twice daily, for eight weeks. [0098] A composition of the present invention showed an initial slow improvement in reducing tryptophan levels.
  • a present composition outperformed the MAP composition and the HQ composition in reducing tryptophan levels.
  • the present composition then outperformed the MAP and HQ compositions for the remainder of the eight- week test.
  • a composition of the present invention also outperformed the MAP and HQ compositions with respect to decreasing the pepsin digestible collagen crosslinks, as measured at 340 ran.
  • FIGs. 1-3 illustrate the improvement provided by an HCA-containing composition of the present invention in reducing skin tryptophan levels and pepsin digestible collagen crosslinks.
  • Figs. 1 and 2 show the substantial reduction in skin tryptophan levels of a present composition compound compared to the MAP and HQ compositions.
  • Figs. 3 and 4 show the substantial reduction in pepsin digestible collagen crosslinks compared to the MAP and HQ compositions.
  • the present composition therefore, provides excellent antiaging effects when applied to the skin in accordance with an extended treatment regimen of at least four weeks, and preferably at least six weeks.
  • the skin treatment can continue indefinitely because the HCA in a present composition is stable and nontoxic.

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Abstract

La présente invention concerne une composition pour le traitement du vieillissement de la peau, et un procédé de traitement de la peau âgée ou stressée. La composition comprend un acide hydroxycinnamique ou un acide méthoxycinnamique et un transporteur approprié pour une application topique de la composition sur la peau humaine. La composition présente des effets anti-âge sur le teint et la fermeté de la peau.
PCT/US2007/085193 2006-12-08 2007-11-20 Composition pour traiter le vieillissement de la peau comprenant un acide hydroxycinnamique tel que l'acide p-coumarique WO2008073684A1 (fr)

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WO2009055860A1 (fr) * 2007-11-02 2009-05-07 Acrux Dds Pty Ltd Système d'administration transdermique
EP2166837A1 (fr) * 2007-06-19 2010-03-31 Prugen, Inc. Combinaison médicamenteuse utilisable pour le traitement de troubles cutanés
FR2951085A1 (fr) * 2009-10-09 2011-04-15 Inst Substances Vegetales Utilisation de composes phenoliques pour la deglycation des proteines
EP2367420A1 (fr) * 2008-12-23 2011-09-28 Avon Products, Inc. Compositions topiques contenant du cis-6-nonénol et ses dérivés et procédés de traitement de la peau
WO2012116744A1 (fr) * 2011-03-02 2012-09-07 Pibed Limited Composition chimique comprenant du peroxyde d'hydrogène et une nanoémulsion d'alcools à longue chaîne
FR2975495A1 (fr) * 2007-07-09 2012-11-23 Engelhard Lyon Methode de criblage de principes actifs favorisant la deglycation des ages
JP2013180954A (ja) * 2012-02-29 2013-09-12 Kose Corp 細胞増殖促進剤、コラーゲン産生促進剤、及び抗シワ剤
US20140179747A1 (en) * 2011-07-25 2014-06-26 Us Cosmeceutechs, Llc Botanical antioxidant compositions and methods of preparation and use thereof
US9066896B2 (en) 2009-12-22 2015-06-30 Avon Products, Inc. Paxillin stimulating compositions and cosmetic uses thereof
WO2016040246A1 (fr) * 2014-09-12 2016-03-17 The Procter & Gamble Company Procédé de production d'une composition de soin de la peau
WO2018017968A1 (fr) * 2016-07-21 2018-01-25 Isa Rebecca Système de revêtement d'ongles
WO2019028214A1 (fr) * 2017-08-03 2019-02-07 Zivmas Llc Composition et procédé permettant de favoriser la croissance des cheveux
WO2023097321A1 (fr) 2021-11-29 2023-06-01 The Procter & Gamble Company Composition de soin de la peau comprenant un acide hydroxycinnamique
WO2023097322A2 (fr) 2021-11-29 2023-06-01 The Procter & Gamble Company Composition pour soins de la peau

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EP2166837A1 (fr) * 2007-06-19 2010-03-31 Prugen, Inc. Combinaison médicamenteuse utilisable pour le traitement de troubles cutanés
EP2166837A4 (fr) * 2007-06-19 2011-12-21 Prugen Inc Combinaison médicamenteuse utilisable pour le traitement de troubles cutanés
FR2975495A1 (fr) * 2007-07-09 2012-11-23 Engelhard Lyon Methode de criblage de principes actifs favorisant la deglycation des ages
EA019760B1 (ru) * 2007-11-02 2014-06-30 АКРУКС ДиДиЭс ПиТиУай ЭлТиДи Система трансдермальной доставки, способ трансдермального введения и способ изготовления системы трансдермальной доставки
WO2009055860A1 (fr) * 2007-11-02 2009-05-07 Acrux Dds Pty Ltd Système d'administration transdermique
EP2367420A1 (fr) * 2008-12-23 2011-09-28 Avon Products, Inc. Compositions topiques contenant du cis-6-nonénol et ses dérivés et procédés de traitement de la peau
EP2367420A4 (fr) * 2008-12-23 2014-08-27 Avon Prod Inc Compositions topiques contenant du cis-6-nonénol et ses dérivés et procédés de traitement de la peau
FR2951085A1 (fr) * 2009-10-09 2011-04-15 Inst Substances Vegetales Utilisation de composes phenoliques pour la deglycation des proteines
WO2011042890A3 (fr) * 2009-10-09 2011-06-03 Institut Des Substances Vegetales Utilisation de composés phénoliques pour la déglycation des protéines
US9066896B2 (en) 2009-12-22 2015-06-30 Avon Products, Inc. Paxillin stimulating compositions and cosmetic uses thereof
WO2012116744A1 (fr) * 2011-03-02 2012-09-07 Pibed Limited Composition chimique comprenant du peroxyde d'hydrogène et une nanoémulsion d'alcools à longue chaîne
CN103429225B (zh) * 2011-03-02 2017-08-15 比贝德有限公司 具有过氧化氢和长链醇的纳米乳状液的化学组合物
CN103429225A (zh) * 2011-03-02 2013-12-04 比贝德有限公司 具有过氧化氢和长链醇的纳米乳状液的化学组合物
US9844216B2 (en) 2011-03-02 2017-12-19 Deb Ip Limited Chemical composition with hydrogen peroxide and a nanoemulsion of long-chained alcohols
US9326932B2 (en) * 2011-07-25 2016-05-03 Us Cosmeceutechs, Llc Botanical antioxidant compositions and methods of preparation and use thereof
US20140179747A1 (en) * 2011-07-25 2014-06-26 Us Cosmeceutechs, Llc Botanical antioxidant compositions and methods of preparation and use thereof
AU2012287067B2 (en) * 2011-07-25 2016-12-08 Dermaforce Holdings, LLC Botanical antioxidant compositions and methods of preparation and use thereof
US9585822B2 (en) * 2011-07-25 2017-03-07 Pcr Technology Holdings, Lc Methods of preparing and using botanical antioxidant compositions
JP2013180954A (ja) * 2012-02-29 2013-09-12 Kose Corp 細胞増殖促進剤、コラーゲン産生促進剤、及び抗シワ剤
WO2016040246A1 (fr) * 2014-09-12 2016-03-17 The Procter & Gamble Company Procédé de production d'une composition de soin de la peau
US9964534B2 (en) 2014-09-12 2018-05-08 The Procter & Gamble Company Method of making a skin care composition
US10054582B2 (en) 2014-09-12 2018-08-21 The Procter & Gamble Company Compositions and methods for inhibiting HMGB1 activation of melanocytes
WO2018017968A1 (fr) * 2016-07-21 2018-01-25 Isa Rebecca Système de revêtement d'ongles
WO2019028214A1 (fr) * 2017-08-03 2019-02-07 Zivmas Llc Composition et procédé permettant de favoriser la croissance des cheveux
US11160750B2 (en) 2017-08-03 2021-11-02 Zivmas Llc Composition and method for promoting hair growth
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