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WO2001070189A1 - Procede et composition destines a l'eclaircissement de la peau utilisant des acides carboxyliques - Google Patents

Procede et composition destines a l'eclaircissement de la peau utilisant des acides carboxyliques Download PDF

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Publication number
WO2001070189A1
WO2001070189A1 PCT/EP2001/002459 EP0102459W WO0170189A1 WO 2001070189 A1 WO2001070189 A1 WO 2001070189A1 EP 0102459 W EP0102459 W EP 0102459W WO 0170189 A1 WO0170189 A1 WO 0170189A1
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WO
WIPO (PCT)
Prior art keywords
acid
composition
alpha
hydroxy carboxylic
weight
Prior art date
Application number
PCT/EP2001/002459
Other languages
English (en)
Inventor
Jonathan David Hague
Original Assignee
Unilever Plc
Unilever Nv
Hindustan Lever Limited
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Unilever Plc, Unilever Nv, Hindustan Lever Limited filed Critical Unilever Plc
Priority to AU2001248333A priority Critical patent/AU2001248333A1/en
Publication of WO2001070189A1 publication Critical patent/WO2001070189A1/fr

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/02—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
    • 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
    • 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
    • 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
    • A61K8/368—Carboxylic acids; Salts or anhydrides thereof with carboxyl groups directly bound to carbon atoms of aromatic rings
    • 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
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/42—Amides
    • 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
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/43—Guanidines

Definitions

  • the present invention relates to a method and composition for lightening the color of skin.
  • Zinc peroxide has been utilized in anhydrous ointments as a bleaching agent.
  • Monobenzyl ether of hydroquinone was marketed for its skin lightening effect but questions of safety also arose.
  • Ascorbic acid preparations either pure or made from a natural material, such as lemon juice, have also been suggested as useful lightening agents. While seemingly entirely safe, they do not appear to be very effective.
  • niacin is effective for skin lightening. This material is postulated as operating by retarding melanin dispersion or distribution into the epidermis. Since unpleasant skin flushing occurs with niacin, the patent suggests the use of niacmamide as a substitute. Compositions based upon niacmamide are effective, but only to a limited extent.
  • U.S. Patent 5,262,153 ( ishima et a l . ) reports the use of lactic acid and salts thereof as skin whitening agents. These must be used at concentrations of at least 5% m order to be effective. However, it s well known that alpha- hydroxy carboxylic acids, such as lactic acid, cause irritation to the skin, especially at higher levels of use.
  • the present invention aims to provide a skin lightening composition and actives to accomplish this function which are more efficient than materials heretofore known and, additionally, are safe to use.
  • a method for lightening the color of skin includes applying to the skin a composition comprising:
  • composition for skm lightening which includes :
  • alpha- and/or beta- hydroxy carboxylic acids in combination with antimicrobial agents can effectively lighten skm.
  • the combination is effective against hyper-pigmentation, age spots and freckles.
  • Use of the aforementioned components together should be incorporated into a regime that applies the compositions repeatedly to the same area of the skm. For instance, the composition may be applied daily for periods from several days to several weeks, before skm lightening becomes evident.
  • a first component of the compositions of the present invention is an alpha- and/or beta- hydroxy carboxylic acid.
  • Illustrative of the beta-hydroxy carboxylic acids is salicylic acid.
  • the alpha-hydroxy carboxylic acids are represented by formula I having the structure:
  • R and R may be the same or different and are selected from H, F, Cl, Br, alkyl, aralkyl or aryl groups which may be saturated or unsaturated, lsomeric or nonisomeric, straight or branched chain, having 1 to 25 carbon atoms, or in a cyclic form having 5 or 6 ring
  • R and R may be substituted with one or more OH, CHO, COOH or alkoxy groups having 1 to 9 carbon atoms.
  • the alpha-hydroxy acid exists as a free acid, and includes stereoisomers, and D, L, and DL forms thereof when
  • R and R are not identical.
  • 2-hydroxyethano ⁇ c acid glycolic acid
  • 2-hydroxypropano ⁇ c acid lactic acid
  • 2-methyl 2- hydroxypropanoic acid methyllactic acid
  • 2-hydroxybutano ⁇ c acid 2-hydroxypentano ⁇ c acid
  • 2-hydroxyhexano ⁇ c acid 2-hydroxyheptano ⁇ c acid
  • 2-hydroxyoctano ⁇ c acid 2- hydroxynonanoic acid
  • 2-hydroxydecano ⁇ c acid 2- hydroxyundecanoic acid
  • 2-hydroxydodecano ⁇ c acid alpha- hydroxylauric acid
  • 2-hydroxytetradecano ⁇ c acid alpha- hydroxymyristic acid
  • 2-hydroxyhexadecano ⁇ c acid alpha- hydroxypalmitic acid
  • 2-hydroxye ⁇ cosano ⁇ c acid alpha- hydroxyarachid
  • glycolic acid lactic acid and 2-hydroxyoctano ⁇ c acid or combinations thereof.
  • Levels of alpha-hydroxy alkanoic acids may range from about 0.1 to about 10%, preferably between about 0.2 and 4%, optimally between about 0.4 and 1% by weight of the composition.
  • the term "acid” is intended to encompass salt forms such as ammonium, t ⁇ ethanolammonium, alkali and alkaline earth metal salts of the alpha- and beta- hydroxy carboxylic acids.
  • Examples include potassium lactate, sodium lactate, potassium glycolate, sodium glycolate, ammonium lactate, ammonium glycolate and any combinations thereof.
  • a mixture of both a beta-hydroxy carboxylic acid and an alpha-hydroxy carboxylic acid there will be present a mixture of both a beta-hydroxy carboxylic acid and an alpha-hydroxy carboxylic acid.
  • the optimum combination is a mixture of salicylic acid and lactic acid in a relative weight ratio from about 20:1 to about 1:20, preferably from about 10:1 to 1:1, optimally from about 3:1 to about 2:1.
  • anti-microbial agent refers to a wide variety of substances having germicidal action, such as the haiogenated salicylamlides , halogenated carbamlides , halogenated bisphenols, alkylbenzoylacrylates , quaternary ammonium compounds, thiuram sulfides, dithiocarbamates, antibiotics, halogenated diphenyl ethers, halogenated anilides of thiophene carboxylic acids, and chlorhexidmes.
  • Suitable halogenated salicylanilides include the following:
  • Suitable bis-phenols include the following:
  • Suitable alkylbenzoyl acrylates comprise the sodium salts of alkylbenzoylacrylic acids wherein the alkyl portion has from about 6 to about 12 carbon atoms.
  • quaternary ammonium compounds include:
  • thiocarbamates and thiuran sulfides examples include :
  • disodium ethylene bis-dithiocarbamate nabam
  • diammonium ethylene bis-dithiocarbamate amabam
  • Zn ethylene bis-dithiocarbamate ziram
  • Mn ethylene bis-dithiocarbamate (manzate) tetramethyl thiuram disulfide; tetrabenzyl thiuram disulfide; tetraethyl thiuram disulfide; tetramethyl thiuram sulfide.
  • N-methyl-N- ( 2-hydroxyethyl-N- (2-hydroxydodecyl ) -N- benzylammonium chloride Especially preferred are:
  • Amounts of the anti-microbial agent may range from about 0.01 to about 5%, preferably from about 0.05 to about 3%, more preferably from about 0.1 to about 1%, optimally from about 0.2 to about 0.6% by weight of the composition.
  • the action of the skm lightening composition is ensured against reversal of melanisation by the presence of an ultraviolet absorbing sunscreen in the composition.
  • sunscreen is meant any material, whether organic or inorganic, which can shield the skm from ultraviolet radiation within the range of 290 to 400 nm.
  • Chromophoric organic sunscreen agents may be divided into the following categories (with specific examples) including: p-ammobenzoic acid, and salts and derivatives thereof (ethyl, isobutyl, glyceryl esters; p-dimethylaminobenzoic acid); Anthramlates (o-ammobenzoates ; methyl, phenyl, benzyl, phen lethyl , lmalyl, terp yl, and cyclonexenyl esters); Salicylates (octyl, amyl, phenyl, benzyl, methyl, glyceryl, and dipropyleneglycol esters); Cmnamic acid derivatives (menthyl and benzyl esters, alpha-phenyl cmnamonit ⁇ le; but
  • 2-ethylhexyl p-methoxycmnamate 4,4'-t-butyl methoxydibenzoylmethane, 2-hydroxy- metho/ybenzophenone, octyldimethylol p-aminobenzoic acid, digalloyltrioleate, 2, 2-dihydroxy-4-methoxybenzophenone, ethyl-4- [bis (hydroxypropyl) ] aminobenzoate, 2-ethylhexyl-2- cyano-3, 3-diphenylacrylate, 2-ethylhexylsalicylate, glyceryl p-aminobenzoate, 3, 3, 5-trimethylcyclohexylsalicylate, methylanthranilate, p-dimethylaminobenzoic acid or aminobenzoate, 2-ethylhexyl p-dimethylaminobenzoate, 2- phenylbenzimid
  • Suitable commercially available organic sunscreen agents are those identified in the following table:
  • Inorganic sunscreen actives may also be employed such as microfine titanium dioxide, zinc oxide, polyethylene, polyamides (e.g. nylon) and various other polymers. Amounts of the sunscreen agents (whether organic or inorganic) will generally range from 0.1 to about 30%, preferably from 2 to 20%, optimally from 4 to 10% by weight of the composition.
  • Compositions of the present invention utilize a pharmaceutically acceptable carrier.
  • the carrier may either be aqueous, anhydrous or an emulsion.
  • the compositions are aqueous, especially water and oil emulsions of the W/O or O/W variety. Water, when present, will be in amounts which may range from 5 to 95%, preferably from 20 to 70%, optimally between 35 and 60% by weight of the composition .
  • relatively volatile solvents may also serve as suitable carriers for the compositions of the present invention.
  • monohydric C 1 -C3 alkanols such as ethyl alcohol, methyl alcohol and isopropyl alcohol.
  • the amount of monohydric alkanol may range from 1 to 70%, preferably from 10 to 50%, optimally between 15 to 40% by weight of the composition.
  • Emollient materials may also serve as pharmaceutically acceptable carriers. These may be m the form of silicone oils or synthetic esters. Amounts of the emollients may range anywhere from 0.1 to 30%, preferably between 1 and 20% by weight of the composition.
  • Silicone oils may be divided into volatile and nonvolatile silicone oils.
  • volatile refers to those materials which have a measurable vapour pressure at ambient temperature.
  • Volatile silicone oils are preferably chosen from cyclic or linear polydimethylsiloxanes containing from 3 to 9, preferably from 4 to 5 silicon atoms. Linear volatile silicone materials generally have viscosities of less than about 5 centistokes at 25°C, while cyclic materials typically have viscosities of less than about 10 centistokes.
  • Nonvolatile silicone oils which are useful as an emollient material for the compositions of the present invention include polyalkyl siloxanes, polyalkylaryl siloxanes and polyether siloxane copolymers.
  • Suitable nonvolatile polyalkyl siloxanes include, for example, polydimethyl siloxanes with viscosities ranging from about 5 to about 100,000 centistokes at 25°C.
  • the preferred nonvolatile emollients useful in the present compositions are polydimethyl siloxanes having viscosities ranging from about 10 to about 400 centistokes at 25°C.
  • Suitable ester emollients include:
  • alkenyl or alkyl esters of fatty acids having 10 to 20 carbon atoms such as isoarachidyl neopentanoate, isononyl isonanonoate, oleyl myristate, oleyl stearate, and oleyl oleate;
  • ether-esters such as fatty acid esters of ethoxylated fatty alcohols
  • polyhyd ⁇ c alcohol esters such as ethylene glycol mono and di-fatty acid esters, diethylene glycol mono- and di-fatty acid esters, polyethylene glycol (200-6000) mono- and di-fatty acid esters, propylene glycol mono- and di- fatty acid ester, polypropylene glycol 2000 monooleate, polypropylene glycol 2000 monostearate, ethoxylated propylene glycol monostearate, glyceryl mono- and di-fatty acid esters, polyglycerol poly-fatty esters, ethoxylated glyceryl monostearate, 1,3-butylene glycol monostearate, 1,3-butylene glycol distearate, polyoxyethylene polyol fatty acid ester, sorbitan fatty acid esters, and polyoxyethylene sorbitan fatty acid esters;
  • polyhyd ⁇ c alcohol esters such as ethylene glycol mono and di-fatty acid esters, diethylene glycol mono- and di-fatty acid
  • Wax esters such as beeswax, spermaceti, my ⁇ styl myristate, stearyl stearate and arachidyl behenate;
  • Sterols esters of which cholesterol fatty acid esters are examples thereof.
  • Fatty acids having from 10 to 30 carbon atoms may also be included as pharmaceutically acceptable carriers for compositions of the present invention.
  • suitable examples include pelargomc, lauric, myristic, palmitic, stea ⁇ c, isostearic, hydroxystearic, oleic, lmoleic, ⁇ cmoleic, arachidic, behenic and erucic acids, preferably stearic
  • Amounts of the fatty acids may range from about 5 to about 50%, preferably from about 10 to about 25%, optimally from about 12 to about 20% by weight of the composition. At levels of 5% or higher, the compositions may be considered as vanishing cream cosmetics.
  • Humectants of the polyhydric alcohol-type may also be employed as suitable pharmaceutically acceptable carriers compositions of the present invention.
  • the humectant helps to increase the effectiveness of the emollients, reduces scaling, stimulates removal of built-up scale and generally improves skm feel.
  • Typical polyhyd ⁇ c alcohols include glycerol, polyalkylene glycols and more preferably alkylene polyols and their derivatives, including propylene glycol, dipropylene glycol, polypropylene glycol, polyethylene glycol and derivatives thereof, sorbitol, hydroxypropyl sorbitol, hexylene glycol, 1,3-butylene glycol, isoprene glycol, 1, 2, 6-hexanetr ⁇ ol, ethoxylated glycerol, propoxylated glycerol and mixtures thereof.
  • the humectant is preferably propylene glycol.
  • the amount of humectant may range anywhere from 0.5 to 30%, preferably between 1 and 15% by weight of the composition.
  • Thickeners may also be utilized as part of the pharmaceutically acceptable carrier of the compositions of the present invention.
  • Typical thickeners include crossl ked acrylates (e.g. Carbopol®) , hydrophobically- modified acrylates (e.g. Pemulen®) , polyacrylamides (e.g. Sepigel 305), cellulosic derivatives and natural gums.
  • useful cellulosic derivatives are sodium carboxymethylcellulose, hydroxypropyl methylcellulose, hydroxypropyl cellulose, hydroxyethyl cellulose, ethyl cellulose and hydroxymethyl cellulose.
  • Natural gums suitable for the present invention include guar, xanthan, sclerotium, carrageenan, pectin, sclerotium and combinations thereof. Amounts of the thickener may range from 0.0001 to 5%, usually from 0.001 to 1%, optimally from 0.01 to 0.5% by weight of the composition. Collectively the water, solvents, silicones, esters, fatty acids, humectants and/or thickeners which constitute the pharmaceutically acceptable carrier will be present in amounts ranging from 1 to 99.9%, preferably from 80 to 99% by weight of the composition.
  • Cosmetic compositions of the present invention may be in any form. These forms may include emulsified systems such as lotions and creams, micro-emulsions, roll-on formulations, mousses, ointments (hydrophilic and hydrophobic) , aerosol and non-aerosol sprays and pad-applied formulations.
  • emulsified systems such as lotions and creams, micro-emulsions, roll-on formulations, mousses, ointments (hydrophilic and hydrophobic) , aerosol and non-aerosol sprays and pad-applied formulations.
  • Surfactants may also be present in the compositions of the present invention.
  • the total concentration of the surfactant may range from 0.1 to 40%, preferably from 1 to
  • the surfactant may be selected from anionic, nonionic, cationic or amphoteric actives.
  • Particularly preferred nonionic surfactants are those with a C 10 -C 20 fatty alcohol or acid hydrophobe condensed with from 2 to 100 moles of ethylene oxide or propylene oxide per mole of hydrophobe;
  • C* 2 _ C lO a lkyl phenols condensed with from 2 to 20 moles of alkylene oxide; mono- and di- fatty acid esters of ethylene glycol; fatty acid monoglyceride; sorbitan, mono- and di-
  • alkyl polyglycosides and saccha ⁇ de fatty amides are also suitable nonionic surfactants.
  • Preferred anionic surfactants include soap, alkyl ether sulfate and sulfonates, alkyl sulfates and sulfonates, alkylbenzene sulfonates, alkyl and dialkyl sulfosuccinates,
  • Preservatives may also desirably be incorporated into the compositions of the present invention to protect against the growth of potentially harmful microorganisms.
  • Suitable traditional preservatives include alkyl esters of para- hydroxybenzoic acid.
  • Other preservatives which have more recently come into use include hydantoin derivatives, propionate salts, and a variety of quaternary ammonium compounds.
  • Cosmetic chemists are familiar with appropriate preservatives and routinely choose them to satisfy the preservative challenge test and to provide product stability. Particularly preferred preservatives are phenoxyethanol, methyl paraben, propyl paraben, butyl paraben, imidazolidinyl urea, sodium dehydroacetate and benzyl alcohol.
  • the preservatives should be selected having regard for the use of the composition and possible incompatibilities between the preservatives and other ingredients in the emulsion. Preservatives are preferably employed in amounts ranging from 0.01% to 2% by weight of the composition.
  • compositions of the present invention may have a pH ranging from about 1 to about 8.5, but preferably on the acidic side with a range from about 2 to about 6.5, preferably from about 3 to about 5.5.
  • Minor adjunct ingredients may also be present in the compositions. Among these may be water-insoluble vitamins such as Vitamin A Palimitate, Vitamin E Acetate and DL- panthenol .
  • compositions of the present invention may also be included in compositions of the present invention.
  • Each of these substances may range from about 0.05 to about 5%, preferably between 0.1 and 3% by weight of the composition.
  • vanishing cream type formulations according to the present invention. These formulations are capable of lightening skin.
  • the method was a randomized, double blind, monadic, vehicle controlled, 12 week use test of various prototype formulations on the face. Subjects were required to come to the test site for a prescreen visit to determine facial baseline. The selected subjects were required to make six additional visits to the test site over a twelve-week period. At baseline (week 0), week 1, 2, 4, 8 and 12, a variety of sk conditions including hyper- pigmentation were evaluated by expert assessors
  • a micro-emulsion formulation according to the present invention is outlined in Table II.
  • a skin lotion (water in oil type) formulation according to the present invention is outlined under Table III. TABLE III
  • a skin cream (oil in water type) with sunscreen formulation according to the present invention is outlined in Table IV.
  • An anhydrous system with an inorganic (titanium dioxide) sunscreen formulation according to the present invention is outlined under Table V.
  • a skin lotion (oil in water type) formulation according to the present invention is outlined in Table VI.
  • a protective skin lotion with sunscreen formulation according to the present invention is outlined in Table VII.

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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)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Emergency Medicine (AREA)
  • Dermatology (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Cosmetics (AREA)

Abstract

L'invention concerne un procédé et une composition destinés à traiter la peau pour l'éclaircir par application d'une composition renfermant un agent antimicrobien, un acide alpha et/ou béta-hydroxy carboxylique et un filtre solaire.
PCT/EP2001/002459 2000-03-21 2001-03-05 Procede et composition destines a l'eclaircissement de la peau utilisant des acides carboxyliques WO2001070189A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU2001248333A AU2001248333A1 (en) 2000-03-21 2001-03-05 Method and composition for skin lightening applying carboxylic acids

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB0006867.6 2000-03-21
GB0006867A GB0006867D0 (en) 2000-03-21 2000-03-21 Method and composition for skin lightening

Publications (1)

Publication Number Publication Date
WO2001070189A1 true WO2001070189A1 (fr) 2001-09-27

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PCT/EP2001/002459 WO2001070189A1 (fr) 2000-03-21 2001-03-05 Procede et composition destines a l'eclaircissement de la peau utilisant des acides carboxyliques

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AU (1) AU2001248333A1 (fr)
GB (1) GB0006867D0 (fr)
WO (1) WO2001070189A1 (fr)
ZA (1) ZA200207066B (fr)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002067886A3 (fr) * 2001-02-28 2003-03-20 Colgate Palmolive Co Composition
WO2005013931A1 (fr) * 2003-07-16 2005-02-17 Ciba Specialty Chemicals Holding Inc. Utilisation de composes d'ether d'hydroxydiphenyle halogenes pour le traitement de la peau
FR2880801A1 (fr) * 2005-01-18 2006-07-21 Oreal Composition de traitement des fibres keratiniques comprenant un alcool aromatique, un acide carboxylique aromatique et un agent protecteur
US9227090B2 (en) 2008-06-18 2016-01-05 Conopco, Inc. Method for lightening skin
WO2020052916A1 (fr) 2018-09-11 2020-03-19 Unilever N.V. Composition topique comprenant un isomérat de saccharide pour un équilibrage du microbiome

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JPH10234356A (ja) * 1997-02-28 1998-09-08 Kosei Sangyo Kk 麹酸を含有する米麹の製造方法
DE19818849A1 (de) * 1997-04-28 1998-10-29 Med Beauty Ag Formulierungen enthaltend Ester der Glycolsäure zur topischen Behandlung der Haut
WO1998058628A1 (fr) * 1997-06-20 1998-12-30 Mary Kay Inc. Composition cosmetique renfermant un agent de blanchiment et un desquamant
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US5874463A (en) * 1994-10-24 1999-02-23 Ancira; Margaret Hydroxy-kojic acid skin peel
FR2735688A1 (fr) * 1995-06-26 1996-12-27 Oreal Utilisation en association d'un alpha-hydroxyacide et d'un oxyde de titane pour le blanchiment de la peau
JPH10234356A (ja) * 1997-02-28 1998-09-08 Kosei Sangyo Kk 麹酸を含有する米麹の製造方法
DE19818849A1 (de) * 1997-04-28 1998-10-29 Med Beauty Ag Formulierungen enthaltend Ester der Glycolsäure zur topischen Behandlung der Haut
WO1998058628A1 (fr) * 1997-06-20 1998-12-30 Mary Kay Inc. Composition cosmetique renfermant un agent de blanchiment et un desquamant
WO1999036053A1 (fr) * 1998-01-16 1999-07-22 Color Access, Inc. Compositions de blanchiment stabilisees et leur procede de preparation

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Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002067886A3 (fr) * 2001-02-28 2003-03-20 Colgate Palmolive Co Composition
WO2005013931A1 (fr) * 2003-07-16 2005-02-17 Ciba Specialty Chemicals Holding Inc. Utilisation de composes d'ether d'hydroxydiphenyle halogenes pour le traitement de la peau
JP2007526893A (ja) * 2003-07-16 2007-09-20 チバ　スペシャルティ　ケミカルズ　ホールディング　インコーポレーテッド 皮膚の処理のためのハロゲン化ヒドロキシジフェニルエーテル化合物の使用
FR2880801A1 (fr) * 2005-01-18 2006-07-21 Oreal Composition de traitement des fibres keratiniques comprenant un alcool aromatique, un acide carboxylique aromatique et un agent protecteur
JP2006199696A (ja) * 2005-01-18 2006-08-03 L'oreal Sa 芳香族アルコール、芳香族カルボン酸、および保護剤を含むケラチン繊維をトリートメントするための組成物
EP1688127A1 (fr) * 2005-01-18 2006-08-09 L'oreal Composition de traitement des fibres kératiniques comprenant un alcool aromatique, un acide carboxylique aromatique et un agent protecteur
US9227090B2 (en) 2008-06-18 2016-01-05 Conopco, Inc. Method for lightening skin
EA026945B1 (ru) * 2008-06-18 2017-06-30 Унилевер Н.В. Композиции для осветления цвета кожи
WO2020052916A1 (fr) 2018-09-11 2020-03-19 Unilever N.V. Composition topique comprenant un isomérat de saccharide pour un équilibrage du microbiome

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