WO1997047171A1 - Skin wash composition - Google Patents

Skin wash composition Download PDF

Info

Publication number
WO1997047171A1
WO1997047171A1 PCT/EP1997/002984 EP9702984W WO9747171A1 WO 1997047171 A1 WO1997047171 A1 WO 1997047171A1 EP 9702984 W EP9702984 W EP 9702984W WO 9747171 A1 WO9747171 A1 WO 9747171A1
Authority
WO
WIPO (PCT)
Prior art keywords
acid
composition
composition according
skin
hydroxy
Prior art date
Application number
PCT/EP1997/002984
Other languages
French (fr)
Inventor
Lynda Rosemary Charlton
Juliet Teresa Mcgillycuddy
Sharon Owen
Original Assignee
Smithkline Beecham Plc
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
Family has litigation
First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=10795020&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=WO1997047171(A1) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Priority to UA98116280A priority Critical patent/UA57023C2/en
Priority to BR9709774A priority patent/BR9709774A/en
Priority to SI9730579T priority patent/SI0906086T1/en
Priority to EA199801001A priority patent/EA001573B1/en
Priority to NZ332864A priority patent/NZ332864A/en
Priority to PL97330603A priority patent/PL186808B1/en
Priority to EP97925065A priority patent/EP0906086B1/en
Priority to SK1687-98A priority patent/SK284219B6/en
Priority to DE69723979T priority patent/DE69723979T2/en
Application filed by Smithkline Beecham Plc filed Critical Smithkline Beecham Plc
Priority to CA002257810A priority patent/CA2257810C/en
Priority to US09/194,383 priority patent/US6162774A/en
Priority to HU0001821A priority patent/HU226084B1/en
Priority to AT97925065T priority patent/ATE246485T1/en
Priority to JP10501179A priority patent/JP2000512636A/en
Priority to DK97925065T priority patent/DK0906086T3/en
Priority to AU30330/97A priority patent/AU720020B2/en
Publication of WO1997047171A1 publication Critical patent/WO1997047171A1/en
Priority to NO19985638A priority patent/NO314218B1/en
Priority to HK99101862A priority patent/HK1016875A1/en
Priority to US10/883,068 priority patent/US7179771B1/en

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/36—Carboxylic acids; Salts or anhydrides 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
    • A61K8/36—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
    • A61K8/362—Polycarboxylic 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
    • A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
    • A61K8/442—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof substituted by amido group(s)
    • 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
    • A61K8/60—Sugars; Derivatives thereof
    • A61K8/604—Alkylpolyglycosides; Derivatives thereof, e.g. esters
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A61K8/87—Polyurethanes
    • 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
    • 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
    • A61P17/10—Anti-acne agents
    • 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
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/88—Ampholytes; Electroneutral compounds
    • C11D1/94—Mixtures with anionic, cationic or non-ionic compounds
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/20—Organic compounds containing oxygen
    • C11D3/2075—Carboxylic acids-salts thereof
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/20—Organic compounds containing oxygen
    • C11D3/2075—Carboxylic acids-salts thereof
    • C11D3/2086—Hydroxy carboxylic acids-salts thereof
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/37—Polymers
    • C11D3/3703—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C11D3/3726—Polyurethanes
    • 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
    • A61K2800/59—Mixtures
    • A61K2800/596—Mixtures of surface active compounds
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/66—Non-ionic compounds
    • C11D1/662—Carbohydrates or derivatives

Definitions

  • the present invention relates to compositions for topical application to the skin surface, in particular to skin wash compositions which are applied to water-wetted skin and subsequently rinsed off with water.
  • the present invention relates to skin wash compositions comprising an ⁇ -hydroxy acid and other acids as defined herein as an active ingredient formulated in a mild and non-irritant detergent base.
  • ⁇ -hydroxy acids and other acids include compounds such as salicylic acid, lactic acid and glycolic acid. These compounds constitute the active ingredients of a number of commercially available products which are applied to the skin in order to confer a beneficial effect with respect to appearance and skin condition, in particular smoothness and suppleness.
  • Salicylic acid for example has been shown to have keratolytic and comedolytic activity as well as anti -bacterial efficacy and has been used in the treatment and prevention of mild to moderate acne for more than 100 years.
  • Lactic acid has a beneficial effect on skin hydration and is a constituent of a number of skin tonic and moisturising products.
  • ⁇ -Hydroxy acids and other acids as defined herein whilst conferring a beneficial effect on the skin, may cause local irritation when applied to sensitive areas of the skin, in particular the face. Moreover, local irritation may be exacerbated by the carrier system in which the active ingredient is formulated.
  • skin wash compositions and in particular face wash compositions which are generally formulated with a soap-free detergent base selected for effective cleansing and foaming, may confer an irritant effect due to the use of ionic surfactants commonly employed in such detergent systems.
  • compositions containing ⁇ -hydroxy acids and other acids as defined herein arises because of the desirability to formulate the composition at an acid pH at which the most efficacious free-acid form of the acid will predominate. For skin wash compositions, this problem is exacerbated by the
  • a skin wash composition described as having a gentle yet effective cleanser for acne treatment and containing 2.0% w/w salicylic acid in a detergent base comprising a mixture of anionic and amphoteric surfactants is commercially available. Analysis of this product, shows that it has a pH of 5. It follows, having regard to the pKa of salicylic acid which is attributed the value 2.97, that the free-acid form of the hydroxy acid does not predominate in this product and that its efficacy is accordingly not fully optimised.
  • a detergent base comprising a mixture of a non-ionic alkylpolyglucoside surfactant and an amphoteric surfactant not only has the desired cleansing and foaming characteristics and is mild and non-irritant when applied to the skin but also enables compositions to be formulated at low pH.
  • a skin wash composition comprising from 0.1 to 10 %w/w of an ⁇ -hydroxy acid or other acid as defined herein and a detergent base consisting of a mixture of a non-ionic alkylpolyglucoside surfactant and an amphoteric surfactant wherein the pH of the composition is in the range 3.0 to 4.5.
  • Suitable acids for incorporation into skin wash compositions of the invention include salicylic acid, lactic acid, citric acid, glycolic acid, malic acid, maleic acid, pyruvic acid and hydroxy-octanoic acid.
  • Preferred acids are salicylic acid, lactic acid and glycolic acid, especially salicylic acid and lactic acid.
  • Salicylic acid will suitably be present in compositions of the invention at a concentration in the range 0.2 to 5.0%> w/w, more suitably in the range 1.0 to 3.0% w/w. A preferred concentration for
  • ISA/EP salicylic acid is 2.0 %w/w.
  • Lactic acid will suitably be present in compositions of the invention at a concentration in the range 0.1 to 5.0 %w/w, more suitably in the range 0.5 to 2.5 %w/w.
  • a preferred concentration for lactic acid is 1 %w/w.
  • Glycolic acid will suitably be present at a concentration in the range 2.0 to 10.0 %w/w.
  • alkylpolyglucoside surfactant means a non-ionic surfactant derived from common natural organic monomer units as found in starch, fats and sugars, and most suitably derived from D-glucose monomer units.
  • Alkylpolyglucosides derived from D-glucose are acetal compounds in which the alkyl residue has a carbon chain length of from 8 to 16 carbon atoms and the degree of glucosidation (or polymerisation), ie. the average number of glucose units per alkyl radical, is between 1.1 and 6.
  • a range of suitable alkylpolyglucosides are commercially available either individually or as mixtures or blends.
  • compositions according to this invention will generally contain mixtures or blends of different alkylpolyglucosides.
  • Preferred alkylpolyglucosides for use in the present invention include decyl glucoside and lauryl glucoside and mixtures thereof.
  • Alkylpolyglucoside surfactants generally comprise up to 20 %w/w of the skin wash composition, suitably from 2.0 to 15.0 %w/w and preferably from 4.0 to 10.0 %w/w of the composition. It will be appreciated that the amount of alkylpolyglucoside will be determined to some extent by the nature and amount of amphoteric surfactant present in the composition.
  • any amphoteric surfactant which is acceptable for topical application to the skin may contribute, with the alkylpolyglucoside surfactant, to the detergent base but, in view of their inherent mildness and good foaming performance, the preferred amphoteric surfactant will belong to the class of compounds known as betaines.
  • betaine compounds contain a carboxylate functional group and a quaternary nitrogen function separated by a methylene moiety. They include n-alkyl betaines such as cetyl betaine and behenyl betaine, and n-alkylamido betaines such as cocoamidopropyl betaine.
  • the amphoteric surfactant component of the detergent base for compositions of the present invention may be a single compound or a mixture of
  • amphoteric surfactant is cocoamidopropyl betaine.
  • Amphoteric surfactants will generally comprise up to 10 %w/w of the skin wash composition, suitably from 2.0 to 8.0 %w/w and preferably from 2.5 to 6.0% w/w of the skin wash composition. The amount of amphoteric surfactant will to some extent be determined by the alkylpolyglucoside surfactant component of the detergent base.
  • the detergent base consisting of the mixture of non-ionic alkylpolyglucoside surfactant and amphoteric surfactant will constitute up to 30 %w/w of the skin wash composition.
  • the detergent base will constitute from 5.0 to 20.0 %w/w and more suitably from 8.0 to 18.0 %w/w of the skin wash composition.
  • Control of pH to within defined limits is an essential feature of the present invention.
  • a pH within the desired range 3.0 to 4.5 is conferred partly by the inherent properties of the acid and specific surfactants and quantities thereof making up the detergent base and partly, where required, by use of a suitable neutralising agent for the acid.
  • Any topically acceptable neutralising agent which is compatible with the other components of the composition can be used. It has been found that the neutralising agent tromethamine is particularly suitable for skin wash compositions containing ⁇ - hydroxy acids or other acids as defined herein.
  • Other suitable neutralising agents include sodium hydroxide and triethanolamine. The amount of neutralising agent will be determined by the acid/base properties of the other ingredients which make up the composition and the pH selected for the composition.
  • the skin wash compositions of the invention may also contain additional topically acceptable skin conditioning and soothing agents, for example in the form of anti- inflammatory agents and vitamins or vitamin derivatives, typically at low concentrations, for example in the range 0.01 to 2.0 %w/w of the total composition.
  • additional topically acceptable skin conditioning and soothing agents include allantoin and
  • a preferred vitamin derivative is vitamin ⁇ acetate which has anti- inflammatory properties.
  • compositions of the present invention will suitably contain pharmaceutically and cosmetically acceptable additives or excipients conventional in the field of topical medicines and cosmetics, including for example thickeners, moisturisers, re-fatting agents, preservatives, conditioners, chelating agents, colouring agents, fragrances, UV filters and/or emulsifiers.
  • additives or excipients used in any given composition will be compatible both with each other and with the essential ingredients of the composition such that there is no interaction which would impair the performance of the active ingredients. All additives or excipients must of course be non-toxic and of sufficient purity to render them suitable for human use.
  • Suitable thickeners include polymeric high molecular weight, non-ionic surfactants consisting of a long chain (C, 2 to C 18 ) polyethylene glycol fatty acid or fatty acid residue. Examples include PEG 200 hydrogenated glyceryl palmitate, PEG 55 propylene glycol oleate, PEG 150 distearate and PEG 200 glyceryl tallowate. Suitable low molecular weight thickeners include cocamide DEA, laureth-3 and glyceryl monolaurate. A thickener comprising a polyurethane resin, propylene glycol and water sold under the trade name Acrysol 44 also performs well in detergent base skin wash compositions.
  • a thickener will suitably comprise up to 10.0 %w/w of the composition, more suitably from 2.0 to 5.0 %w/w.
  • Preferred moisturisers include glycerin, propylene glycol, sorbitol and polyethylene glycol.
  • a moisturiser may comprise up to 15%w/w of the composition, more generally from 2.0 to 6.0 %w/w of the composition.
  • Suitable re-fatting agents generally comprising 0.5 to 5.0 %w/w of the composition, preferably 0.75 to 2.0 %w/w include polyethylene glycol 7 and glyceryl cocoate.
  • Suitable preservatives generally comprising 0.01 to 1.00 %w/w of the composition and suitably 0.10 to 0.30 %w/w, include phenoxyethanol and methyl dibromo glutaronitrile and mixtures thereof.
  • Suitable conditioners generally comprising 0.1 to 5.0 %w/w of the composition and suitably 1.0 to 3.5%w/w include hydroxycetyl hydroxy ethyl dimonium chloride and polyquaternium 39.
  • ISA/EP chelating agents generally comprising up to 1.0 %w/w of the composition and suitably 0.1 to 0.3 %w/w include ethylene diamine tetra-acetic acid (EDTA), hydroethylene diamine triacetic acid (HEEDTA), diethylene triamine penta-acetic acid (DPTA) and cyclohexane diamine tetra-acetic acid (CTDA).
  • EDTA ethylene diamine tetra-acetic acid
  • HEEDTA hydroethylene diamine triacetic acid
  • DPTA diethylene triamine penta-acetic acid
  • CTDA cyclohexane diamine tetra-acetic acid
  • the balance of the composition is typically water and/or other non-alcohol solvent so as to make up 100 %w/w of the composition.
  • the preferred solvent is water which will generally constitute more than 50 %w/w of the skin wash composition.
  • Other suitable non-alcohol solvents which may be included to aid solution of the ⁇ -hydroxy acid include glycols such as propylene glycol and macrogols.
  • the skin wash compositions of the invention may be prepared by methods well known in the art and readily available to the skilled formulator. Generally the acid and the surfactants making up the detergent base, together with any additives, are dissolved in solvent, the pH of the resulting mixture is checked and adjusted if appropriate and the viscosity of the composition is set to the desired level by addition of thickening agents.
  • the present invention extends to a process for preparing a skin wash composition as hereinbefore defined comprising the admixture of the ⁇ -hydroxy acid or other acid as defined herein with the detergent base in an aqueous solvent system and adjusting the pH as required such that the pH of the composition is in the range 3.0 to 4.5.
  • the present invention additionally encompasses the use of a skin wash composition as hereinbefore defined wherein the acid is salicylic acid for the manufacture of a medicament for the treatment and/or prophylaxis of acne.
  • compositions of the present invention as hereinbefore defined as a cosmetic treatment for improving the appearance and condition of human skin also forms part of the invention.
  • composition comprising the following ingredients was prepared.
  • the resulting composition had a pH of approximately 3.5.
  • Example 2 Skin Wash Composition containing Salicylic Acid
  • composition comprising the following ingredients was prepared.
  • the resulting composition was a clear product having a pH of 4.5.
  • Example 2 The composition of Example 2 containing the additional excipents indicated below was prepared.
  • the resulting clear product had a pH of 4.5.
  • conditioner hydroxycetyl hydroxyethyl dimonium chloride chelating agent EDTA preservative phenoxyethanol anti-inflammatory agent allantoin & vitamin E acetate

Abstract

A skin wash composition intended for topical application to water-wetted skin comprising an α-hydroxy acid active ingredient formulated in a mild and non-irritant detergent base consisting of a mixture of a non-ionic alkylpolyglucoside surfactant and an amphoteric surfactant.

Description

SKIN WASH COMPOSITION
The present invention relates to compositions for topical application to the skin surface, in particular to skin wash compositions which are applied to water-wetted skin and subsequently rinsed off with water. Specifically, the present invention relates to skin wash compositions comprising an α-hydroxy acid and other acids as defined herein as an active ingredient formulated in a mild and non-irritant detergent base.
Compounds generally known in the field of cosmetic and therapeutic skin treatments as α-hydroxy acids and other acids as defined herein include compounds such as salicylic acid, lactic acid and glycolic acid. These compounds constitute the active ingredients of a number of commercially available products which are applied to the skin in order to confer a beneficial effect with respect to appearance and skin condition, in particular smoothness and suppleness. Salicylic acid for example has been shown to have keratolytic and comedolytic activity as well as anti -bacterial efficacy and has been used in the treatment and prevention of mild to moderate acne for more than 100 years. Lactic acid has a beneficial effect on skin hydration and is a constituent of a number of skin tonic and moisturising products.
α-Hydroxy acids and other acids as defined herein, whilst conferring a beneficial effect on the skin, may cause local irritation when applied to sensitive areas of the skin, in particular the face. Moreover, local irritation may be exacerbated by the carrier system in which the active ingredient is formulated. For example, skin wash compositions and in particular face wash compositions which are generally formulated with a soap-free detergent base selected for effective cleansing and foaming, may confer an irritant effect due to the use of ionic surfactants commonly employed in such detergent systems.
A further problem associated with formulating compositions containing α-hydroxy acids and other acids as defined herein arises because of the desirability to formulate the composition at an acid pH at which the most efficacious free-acid form of the acid will predominate. For skin wash compositions, this problem is exacerbated by the
- 1 -
RECTIFIED SHEET (RULE 91) ISA/EP difficulty of obtaining a detergent base system at Sufficiently low pH. A skin wash composition described as having a gentle yet effective cleanser for acne treatment and containing 2.0% w/w salicylic acid in a detergent base comprising a mixture of anionic and amphoteric surfactants is commercially available. Analysis of this product, shows that it has a pH of 5. It follows, having regard to the pKa of salicylic acid which is attributed the value 2.97, that the free-acid form of the hydroxy acid does not predominate in this product and that its efficacy is accordingly not fully optimised.
It is an object of the present invention to provide a skin wash composition containing an α-hydroxy acid or other acid as defined herein and a detergent base which has good cleansing and foaming characteristics, is mild and non-irritant and wherein the pH of the composition approaches the pKa of the acid such that the efficacy of the acid is enhanced. This object is achieved according to the present invention which is based on the unexpected finding that a detergent base comprising a mixture of a non-ionic alkylpolyglucoside surfactant and an amphoteric surfactant not only has the desired cleansing and foaming characteristics and is mild and non-irritant when applied to the skin but also enables compositions to be formulated at low pH.
According to the present invention there is provided a skin wash composition comprising from 0.1 to 10 %w/w of an α-hydroxy acid or other acid as defined herein and a detergent base consisting of a mixture of a non-ionic alkylpolyglucoside surfactant and an amphoteric surfactant wherein the pH of the composition is in the range 3.0 to 4.5.
Suitable acids for incorporation into skin wash compositions of the invention include salicylic acid, lactic acid, citric acid, glycolic acid, malic acid, maleic acid, pyruvic acid and hydroxy-octanoic acid. Preferred acids are salicylic acid, lactic acid and glycolic acid, especially salicylic acid and lactic acid. Salicylic acid will suitably be present in compositions of the invention at a concentration in the range 0.2 to 5.0%> w/w, more suitably in the range 1.0 to 3.0% w/w. A preferred concentration for
- 2 -
RECTIFIED SHEET (RULE 91) ISA/EP salicylic acid is 2.0 %w/w. Lactic acid will suitably be present in compositions of the invention at a concentration in the range 0.1 to 5.0 %w/w, more suitably in the range 0.5 to 2.5 %w/w. A preferred concentration for lactic acid is 1 %w/w. Glycolic acid will suitably be present at a concentration in the range 2.0 to 10.0 %w/w.
As used herein, the term alkylpolyglucoside surfactant means a non-ionic surfactant derived from common natural organic monomer units as found in starch, fats and sugars, and most suitably derived from D-glucose monomer units. Alkylpolyglucosides derived from D-glucose are acetal compounds in which the alkyl residue has a carbon chain length of from 8 to 16 carbon atoms and the degree of glucosidation (or polymerisation), ie. the average number of glucose units per alkyl radical, is between 1.1 and 6. A range of suitable alkylpolyglucosides are commercially available either individually or as mixtures or blends. Compositions according to this invention will generally contain mixtures or blends of different alkylpolyglucosides. Preferred alkylpolyglucosides for use in the present invention include decyl glucoside and lauryl glucoside and mixtures thereof. Alkylpolyglucoside surfactants generally comprise up to 20 %w/w of the skin wash composition, suitably from 2.0 to 15.0 %w/w and preferably from 4.0 to 10.0 %w/w of the composition. It will be appreciated that the amount of alkylpolyglucoside will be determined to some extent by the nature and amount of amphoteric surfactant present in the composition.
In principle, any amphoteric surfactant which is acceptable for topical application to the skin may contribute, with the alkylpolyglucoside surfactant, to the detergent base but, in view of their inherent mildness and good foaming performance, the preferred amphoteric surfactant will belong to the class of compounds known as betaines. Structurally, betaine compounds contain a carboxylate functional group and a quaternary nitrogen function separated by a methylene moiety. They include n-alkyl betaines such as cetyl betaine and behenyl betaine, and n-alkylamido betaines such as cocoamidopropyl betaine. The amphoteric surfactant component of the detergent base for compositions of the present invention may be a single compound or a mixture of
RECTIFIED SHEET (RULE 91) ISA/EP blend of two or more different substances. A preferred amphoteric surfactant is cocoamidopropyl betaine. Amphoteric surfactants will generally comprise up to 10 %w/w of the skin wash composition, suitably from 2.0 to 8.0 %w/w and preferably from 2.5 to 6.0% w/w of the skin wash composition. The amount of amphoteric surfactant will to some extent be determined by the alkylpolyglucoside surfactant component of the detergent base.
Typically, the detergent base consisting of the mixture of non-ionic alkylpolyglucoside surfactant and amphoteric surfactant will constitute up to 30 %w/w of the skin wash composition. Suitably the detergent base will constitute from 5.0 to 20.0 %w/w and more suitably from 8.0 to 18.0 %w/w of the skin wash composition.
Control of pH to within defined limits is an essential feature of the present invention. A pH within the desired range 3.0 to 4.5 is conferred partly by the inherent properties of the acid and specific surfactants and quantities thereof making up the detergent base and partly, where required, by use of a suitable neutralising agent for the acid. Any topically acceptable neutralising agent which is compatible with the other components of the composition can be used. It has been found that the neutralising agent tromethamine is particularly suitable for skin wash compositions containing α- hydroxy acids or other acids as defined herein. Other suitable neutralising agents include sodium hydroxide and triethanolamine. The amount of neutralising agent will be determined by the acid/base properties of the other ingredients which make up the composition and the pH selected for the composition.
The skin wash compositions of the invention may also contain additional topically acceptable skin conditioning and soothing agents, for example in the form of anti- inflammatory agents and vitamins or vitamin derivatives, typically at low concentrations, for example in the range 0.01 to 2.0 %w/w of the total composition. Examples of topically acceptable anti-inflammatory agents include allantoin and
- 4 -
RECTIFIED SHEET (RULE 91) ISA/EP bisabolol. A preferred vitamin derivative is vitamin Ξ acetate which has anti- inflammatory properties.
Additionally, compositions of the present invention will suitably contain pharmaceutically and cosmetically acceptable additives or excipients conventional in the field of topical medicines and cosmetics, including for example thickeners, moisturisers, re-fatting agents, preservatives, conditioners, chelating agents, colouring agents, fragrances, UV filters and/or emulsifiers. The additives or excipients used in any given composition will be compatible both with each other and with the essential ingredients of the composition such that there is no interaction which would impair the performance of the active ingredients. All additives or excipients must of course be non-toxic and of sufficient purity to render them suitable for human use.
Suitable thickeners include polymeric high molecular weight, non-ionic surfactants consisting of a long chain (C,2 to C18) polyethylene glycol fatty acid or fatty acid residue. Examples include PEG 200 hydrogenated glyceryl palmitate, PEG 55 propylene glycol oleate, PEG 150 distearate and PEG 200 glyceryl tallowate. Suitable low molecular weight thickeners include cocamide DEA, laureth-3 and glyceryl monolaurate. A thickener comprising a polyurethane resin, propylene glycol and water sold under the trade name Acrysol 44 also performs well in detergent base skin wash compositions. A thickener will suitably comprise up to 10.0 %w/w of the composition, more suitably from 2.0 to 5.0 %w/w. Preferred moisturisers include glycerin, propylene glycol, sorbitol and polyethylene glycol. A moisturiser may comprise up to 15%w/w of the composition, more generally from 2.0 to 6.0 %w/w of the composition. Suitable re-fatting agents generally comprising 0.5 to 5.0 %w/w of the composition, preferably 0.75 to 2.0 %w/w include polyethylene glycol 7 and glyceryl cocoate. Suitable preservatives generally comprising 0.01 to 1.00 %w/w of the composition and suitably 0.10 to 0.30 %w/w, include phenoxyethanol and methyl dibromo glutaronitrile and mixtures thereof. Suitable conditioners, generally comprising 0.1 to 5.0 %w/w of the composition and suitably 1.0 to 3.5%w/w include hydroxycetyl hydroxy ethyl dimonium chloride and polyquaternium 39. Suitable
RECTIFIED SHEET (RULE 91) ISA/EP chelating agents, generally comprising up to 1.0 %w/w of the composition and suitably 0.1 to 0.3 %w/w include ethylene diamine tetra-acetic acid (EDTA), hydroethylene diamine triacetic acid (HEEDTA), diethylene triamine penta-acetic acid (DPTA) and cyclohexane diamine tetra-acetic acid (CTDA).
The balance of the composition is typically water and/or other non-alcohol solvent so as to make up 100 %w/w of the composition. The preferred solvent is water which will generally constitute more than 50 %w/w of the skin wash composition. Other suitable non-alcohol solvents which may be included to aid solution of the α-hydroxy acid include glycols such as propylene glycol and macrogols.
The skin wash compositions of the invention may be prepared by methods well known in the art and readily available to the skilled formulator. Generally the acid and the surfactants making up the detergent base, together with any additives, are dissolved in solvent, the pH of the resulting mixture is checked and adjusted if appropriate and the viscosity of the composition is set to the desired level by addition of thickening agents. The present invention extends to a process for preparing a skin wash composition as hereinbefore defined comprising the admixture of the α-hydroxy acid or other acid as defined herein with the detergent base in an aqueous solvent system and adjusting the pH as required such that the pH of the composition is in the range 3.0 to 4.5.
The present invention additionally encompasses the use of a skin wash composition as hereinbefore defined wherein the acid is salicylic acid for the manufacture of a medicament for the treatment and/or prophylaxis of acne. The use of compositions of the present invention as hereinbefore defined as a cosmetic treatment for improving the appearance and condition of human skin also forms part of the invention.
The following examples further describe and demonstrate compositions falling within the scope of the invention. For the avoidance of doubt, the examples are solely for the purpose of illustration and are not limiting with respect to the scope of the invention.
- 6 -
RECTIFIED SHEET (RULE 91) ISA/EP Example 1 - Skin Wash Composition containing Lactic Acid
A composition comprising the following ingredients was prepared. The resulting composition had a pH of approximately 3.5.
Ingredient %w/w α-hydroxy acid : lactic acid 1.0 detergent base : decyl glucoside 3.5 lauryl glucoside 3.6 cocoamidopropyl betaine 5.0 thickener PEG 120 methyl glucose dioleate 3.2 preservative phenoxyethanol 0.25 solvent water to 100 %o
Example 2 - Skin Wash Composition containing Salicylic Acid
A composition comprising the following ingredients was prepared. The resulting composition was a clear product having a pH of 4.5.
Ingredient %w/w acid salicylic acid 2.0 detergent base lauryl glucoside 2.4 decyl glucoside 2.0 cocamidopropyl betaine 2.8 neutralising agent Tromethamine 1.5 thickener PEG 120 methyl glucose dioleate 4.0 solvent de-ionised water to 100 %
- 7 -
RECTIFIED SHEET (RULE 91) ISA/EP Example 3 - Skin Wash Composition containing Salicylic Acid
The composition of Example 2 containing the additional excipents indicated below was prepared. The resulting clear product had a pH of 4.5.
conditioner hydroxycetyl hydroxyethyl dimonium chloride chelating agent EDTA preservative phenoxyethanol anti-inflammatory agent allantoin & vitamin E acetate
- 8 -
RECTIFIED SHEET (RULE 91) ISA/EP

Claims

1. A skin wash composition comprising from 0.1 to 10 %w/w of an α-hydroxy acid or other acid as defined herein and a detergent base consisting of a mixture of a non- ionic alkylpolyglucoside surfactant and an amphoteric surfactant wherein the pH of the said composition is in the range 3.0 to 4.5.
2. A composition according to claim 1 wherein the acid is citric acid, malic acid, maleic acid, pyruvic acid, hydroxy-octanoic acid, salicylic acid, lactic acid or glycolic acid.
3. A composition according to claim 2 wherein the acid is salicyclic acid.
4. A composition according to claim 3 comprising from 0.2 to 5.0%> w/w salicylic acid.
5. A composition according to claim 4 comprising 1.0 to 3.0%) w/w salicylic acid.
6. A composition according to claim 2 wherein the α-hydroxy acid is lactic acid which comprises from 0.1 to 5.0%) w/w of the composition.
7. A composition according to claim 6 comprising from 0.5 to 2.5% w/w lactic acid.
8. A composition according to claim 2 wherein the α-hydroxy acid is glycolic acid which comprises from 2.0 to 10.0% w/w of the composition.
9. A composition according to any one of claims 1 to 8 wherein the alkylpolyglucoside surfactant is decyl glucoside, lauryl glucoside or mixtures thereof.
10. A composition according to any one of claims 1 to 9 wherein the alkylpolyglucoside surfactant comprises up to 20%) w/w of the said composition.
11. A composition according to claim 10 wherein the alkylpolyglucoside surfactant comprises from 2.0 to 15%> w/w of the composition.
12. A composition according to any one of claims 1 to 1 1 wherein the amphoteric surfactant comprises at least one betaine.
13. A composition according to claim 12 wherein the betaine is cocoamidopropyl betaine.
14. A composition according to any one of claims 1 to 13 wherein the amphoteric surfactant comprises up to 10%> w/w of the said composition.
15. A composition according to claim 14 wherein the amphoteric surfactant comprises from 2.0 to 8.0%> w/w of the composition.
- 9 -
RECTIFIED SHEET (RULE 91) ISA/EP
16. A composition according to any one of claims 1 to 15 wherein the detergent base comprises up to 30% w/w of the said composition.
17. A composition according to any one of claims 1 to 16 further comprising a neutralizing agent.
18. A composition according to claim 17 wherein the said neutralizing agent is tromethamine, sodium hydroxide or triethanolamine.
19. A composition according to any preceding claim substantially as described herein with reference to the examples.
20. A method for the preparation of a composition as defined in any of claims 1 to 19, which method comprises admixing the α-hydroxy acid or other acid as defined herein with the detergent base in an aqueous solvent system and adjusting the pH as required.
21. A composition as defined in any one of claims 3 to 5 and 9 to 20 for use in the treatment and/or prophylaxis of acne.
22. Use of a composition as defined in any one of claims 3 to 5 and 9 to 20 in the manufacture of a medicament for use in the treatment and/or prophylaxis of acne.
23. A method of treatment and/or prophylaxis of acne which comprises the administration of an effective amount of a pharmaceutical composition as defined in any one of claims 3 to 5 and 9 to 20.
24. Use of a composition as defined in any one of claims 1 to 19 as a cosmetic treatment for improving the appearance and condition of human skin.
- 10 -
RECTIFIED SHEET (RULE 91) ISA/EP
PCT/EP1997/002984 1996-06-10 1997-06-05 Skin wash composition WO1997047171A1 (en)

Priority Applications (19)

Application Number Priority Date Filing Date Title
UA98116280A UA57023C2 (en) 1996-06-10 1997-05-06 Skin wash composition intended for topical application, method for its preparation, method for treating skin, remedy for skin care
AU30330/97A AU720020B2 (en) 1996-06-10 1997-06-05 Skin wash composition
CA002257810A CA2257810C (en) 1996-06-10 1997-06-05 Skin wash composition comprising an .alpha.-hydroxy acid or other acid and a detergent base
EA199801001A EA001573B1 (en) 1996-06-10 1997-06-05 Skin wash composition, method of preparation and use
NZ332864A NZ332864A (en) 1996-06-10 1997-06-05 Skin wash composition comprising an alpha-hydroxy, salicyclic, maleic or pyruvic acid
PL97330603A PL186808B1 (en) 1996-06-10 1997-06-05 Skin washing composition
EP97925065A EP0906086B1 (en) 1996-06-10 1997-06-05 Skin wash composition
SK1687-98A SK284219B6 (en) 1996-06-10 1997-06-05 Composition
DE69723979T DE69723979T2 (en) 1996-06-10 1997-06-05 SKIN CLEANERS
BR9709774A BR9709774A (en) 1996-06-10 1997-06-05 Skin wash composition
SI9730579T SI0906086T1 (en) 1996-06-10 1997-06-05 Skin wash composition
US09/194,383 US6162774A (en) 1996-06-10 1997-06-05 Skin wash composition
HU0001821A HU226084B1 (en) 1996-06-10 1997-06-05 Skin wash composition, process for producing and use thereof
AT97925065T ATE246485T1 (en) 1996-06-10 1997-06-05 SKIN CLEANSER
JP10501179A JP2000512636A (en) 1996-06-10 1997-06-05 Skin cleansing composition
DK97925065T DK0906086T3 (en) 1996-06-10 1997-06-05 skin wash composition
NO19985638A NO314218B1 (en) 1996-06-10 1998-12-03 Skin wash composition, method of preparation of same, use of same for preparation of drug and application of same wood cosmetic treatment
HK99101862A HK1016875A1 (en) 1996-06-10 1999-04-27 Skin wash composition
US10/883,068 US7179771B1 (en) 1996-06-10 2004-06-30 Composition

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB9612067.0 1996-06-10
GBGB9612067.0A GB9612067D0 (en) 1996-06-10 1996-06-10 Composition

Related Child Applications (3)

Application Number Title Priority Date Filing Date
US09/194,383 A-371-Of-International US6162774A (en) 1996-06-10 1997-06-05 Skin wash composition
US09194383 A-371-Of-International 1997-06-05
US09/693,055 Continuation-In-Part US6486106B1 (en) 1996-06-10 2000-10-20 Composition

Publications (1)

Publication Number Publication Date
WO1997047171A1 true WO1997047171A1 (en) 1997-12-18

Family

ID=10795020

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1997/002984 WO1997047171A1 (en) 1996-06-10 1997-06-05 Skin wash composition

Country Status (30)

Country Link
US (4) US6162774A (en)
EP (1) EP0906086B1 (en)
JP (1) JP2000512636A (en)
KR (1) KR20000016515A (en)
CN (1) CN1121211C (en)
AR (1) AR007542A1 (en)
AT (1) ATE246485T1 (en)
AU (1) AU720020B2 (en)
BR (1) BR9709774A (en)
CA (1) CA2257810C (en)
CY (1) CY2506B1 (en)
CZ (1) CZ293773B6 (en)
DE (1) DE69723979T2 (en)
DK (1) DK0906086T3 (en)
EA (1) EA001573B1 (en)
ES (1) ES2206714T3 (en)
GB (1) GB9612067D0 (en)
HK (1) HK1016875A1 (en)
HU (1) HU226084B1 (en)
MY (1) MY124104A (en)
NO (1) NO314218B1 (en)
NZ (1) NZ332864A (en)
PL (1) PL186808B1 (en)
PT (1) PT906086E (en)
SI (1) SI0906086T1 (en)
SK (1) SK284219B6 (en)
TW (1) TW460294B (en)
UA (1) UA57023C2 (en)
WO (1) WO1997047171A1 (en)
ZA (1) ZA975062B (en)

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6998372B2 (en) 2001-08-16 2006-02-14 J&J Consumer Companies, Inc. Moisturizing detergent compositions
EP1975224A1 (en) * 2007-03-30 2008-10-01 Johnson & Johnson Consumer France SAS Mild, foaming cleansing composition
EP2378872A1 (en) * 2008-12-18 2011-10-26 B. Eugene Guthery Acne vulgaris treatment regimen
WO2012011892A1 (en) * 2010-07-19 2012-01-26 Colgate-Palmolive Company Cleansing composition with decyl and coco glucosides
EP1997537A3 (en) * 2007-05-23 2012-02-01 Coty Prestige Lancaster Group GmbH Cosmetic skin cleaning product
WO2016028177A1 (en) * 2014-08-21 2016-02-25 Uniwersytet Przyrodniczy W Poznaniu Liquid biostimulator increasing resistance of agricultural plants to stress conditions
WO2016037853A1 (en) * 2014-09-11 2016-03-17 Bode Chemie Gmbh Tuberculocidal disinfectant
WO2019212711A1 (en) * 2018-04-30 2019-11-07 L'oreal Gentle cleanser compositions

Families Citing this family (41)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB9612067D0 (en) * 1996-06-10 1996-08-14 Smithkline Beecham Plc Composition
US20030072814A1 (en) * 1999-12-16 2003-04-17 Maibach Howard I. Topical pharmaceutical composition for the treatment of warts
US20030077301A1 (en) * 1999-12-16 2003-04-24 Maibach Howard I. Topical pharmaceutical composition for the treatment of inflammatory dermatoses
AU2001255487A1 (en) * 2000-04-21 2001-11-07 Nature's Cure Salicylic acid acne spray formulations and methods for treating acne with same
JP2002129192A (en) * 2000-10-26 2002-05-09 Japan Natural Laboratory Co Ltd Method for producing transparent solid detergent composition
US6780825B2 (en) 2001-02-06 2004-08-24 Playtex Products, Inc. Cleansing compositions with milk protein and aromatherapy
US20050143267A1 (en) * 2001-02-06 2005-06-30 Playtex Products, Inc. Pearlized cleanser composition with milk protein and aromatherapy and method of making same
DE10118269A1 (en) * 2001-04-12 2002-10-17 Cognis Deutschland Gmbh Production of polyetherurethane thickeners, useful in cosmetic compositions for, e.g. skin or hair, comprises reacting an ethoxylated fatty alcohol with an aliphatic di- or triisocyanate
JP3767498B2 (en) 2002-03-05 2006-04-19 富士ゼロックス株式会社 Cleaning method for charging roll
US6821523B2 (en) 2002-06-21 2004-11-23 Dermatrends, Inc. Topical administration of pharmacologically active bases in the treatment of warts
US6943197B2 (en) 2002-06-21 2005-09-13 Howard I. Maibach Topical administration of pharmacologically active bases in the treatment of inflammatory dermatoses
DE10301836A1 (en) * 2003-01-20 2004-07-29 Beiersdorf Ag Cosmetic or dermatological preparations with a pearlescent look
DE10301834A1 (en) * 2003-01-20 2004-07-29 Beiersdorf Ag Cosmetic or dermatological preparations with an improved pearlescent look
US8951947B2 (en) * 2003-12-24 2015-02-10 The Procter & Gamble Company Multi-phase personal cleansing compositions comprising a lathering cleansing phase and a non-lathering structured aqueous phase
US20050201965A1 (en) * 2004-03-11 2005-09-15 The Procter & Gamble Company Personal cleansing compositions
MX2007008012A (en) * 2004-12-30 2007-08-23 Rhone Poulenc Chimie Herbicidal composition comprising an aminophosphate or aminophosphonate salt and a betaine.
CA2629862C (en) * 2005-11-14 2014-03-18 Rhodia Inc. Agricultural adjuvant compositions, pesticide compositions, and methods for using such compositions
US8715700B2 (en) * 2006-07-21 2014-05-06 Dow Pharmaceutical Sciences, Inc. Alpha hydroxy acid sustained release formulation
WO2008066611A2 (en) * 2006-10-16 2008-06-05 Rhodia Inc. Agricultural adjuvant compositions. pesticide compositions. and methods for using such compositions
KR101283303B1 (en) * 2007-01-31 2013-07-12 (주)아모레퍼시픽 Composition for external use containing stable α-keto acids obtained by controlling pH of the composition, and method for stabilizing the α-keto acids
FR2914647B1 (en) * 2007-04-05 2011-10-21 Rhodia Recherches Et Tech COPOLYMER COMPRISING BETAINIC UNITS AND HYDROPHOBIC AND / OR AMPHIPHILIC UNITS, PREPARATION METHOD, AND USES.
DE102007041494A1 (en) 2007-08-31 2009-03-05 Henkel Ag & Co. Kgaa Cosmetic cleanser with low pH
CN101932236A (en) * 2007-11-07 2010-12-29 罗地亚管理公司 Herbicidal composition comprising an aminophosphate or aminophosphonate salt and a viscosity reducing agent
KR101601018B1 (en) * 2008-11-07 2016-03-08 (주)아모레퍼시픽 Mild composition for skin external application under the weak acid conditions
BR112012001048A8 (en) 2009-07-14 2017-04-18 Rhodia Operations AGRICULTURAL ADJUVANT COMPOSITIONS, PESTICIDE COMPOSITIONS, AND METHODS OF USE OF SUCH COMPOSITIONS.
US9180112B2 (en) * 2010-03-23 2015-11-10 Ermis Labs, LLC Dermal compositions containing gorgonian extract
WO2012021164A2 (en) 2010-08-10 2012-02-16 Rhodia Operations Agricultural pesticide compositions
US9562834B2 (en) * 2014-08-21 2017-02-07 John J. Nelson Aqueous compositions and methods of using the same for histopathological evaluation of tissue samples
WO2016026710A1 (en) * 2014-08-21 2016-02-25 Alfa Parf Group S.P.A. Cosmetic composition for keratin fibres
DE202015008361U1 (en) 2014-12-03 2016-04-21 Mary Kay Inc. Cosmetic compositions
US9657254B1 (en) * 2015-12-29 2017-05-23 Kim Landeweer Paint, ink and resin remover composition
CA3024785A1 (en) * 2016-07-26 2018-02-01 Colgate-Palmolive Company Liquid cleansing compositions with an antibacterial system and method of manufacturing thereof
WO2018237218A1 (en) 2017-06-23 2018-12-27 The Procter & Gamble Company Composition and method for improving the appearance of skin
KR102635195B1 (en) * 2017-11-24 2024-02-13 (주)아모레퍼시픽 An aqueous solution for solubilizing salicylic acid, a process thereof, and a cosmetic composition comprising them
CA3102288A1 (en) 2018-07-03 2020-01-09 The Procter & Gamble Company Method of treating a skin condition
CN109055048B (en) * 2018-07-17 2020-11-10 北京枫华草木洗涤用品有限公司 Pure natural moisturizing and acne removing handmade soap and preparation method and application thereof
WO2020029223A1 (en) * 2018-08-10 2020-02-13 Beiersdorf Daily Chemical (Wuhan) Co. Ltd. A foamable cleansing composition
TWI670257B (en) * 2018-12-21 2019-09-01 謝天傑 Vanillin tetramer structure
US10959933B1 (en) 2020-06-01 2021-03-30 The Procter & Gamble Company Low pH skin care composition and methods of using the same
CN115843238A (en) 2020-06-01 2023-03-24 宝洁公司 Method for improving penetration of vitamin b3 compounds into the skin
JP2023539426A (en) 2020-07-31 2023-09-14 パン－モントージョ，フランシスコ About the pharmaceutical combination of glycolic acid and L-alanine

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1993025650A1 (en) * 1992-06-16 1993-12-23 Henkel Corporation Viscosity-adjusted surfactant concentrate compositions
US5429815A (en) * 1994-04-11 1995-07-04 Chesebrough-Pond's Usa Co., Division Of Conopco, Inc. Stable single-phase self-foaming cleanser
DE4408228A1 (en) * 1994-03-11 1995-09-14 Henkel Kgaa Low viscosity aqueous concentrate of betaine surfactants
DE19504914C1 (en) * 1995-02-15 1995-11-16 Goldwell Gmbh Hair washing agent giving gloss and body, and easy combing
WO1995031962A1 (en) * 1994-05-20 1995-11-30 Gojo Industries, Inc. Antimicrobial cleaning composition containing chlorhexidine, anamphoteric and an alkylpolyglucoside
WO1996002225A1 (en) * 1994-07-19 1996-02-01 Unilever Plc Detergent composition
DE4435495A1 (en) * 1994-10-04 1996-04-11 Henkel Kgaa Pumpable aqueous surfactant concentrates

Family Cites Families (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4971800A (en) 1988-07-08 1990-11-20 The Regents Of The University Of California Method and compositions for enhancing the cutaneous penetration of pharmacologically active agents
US5045317A (en) 1987-07-16 1991-09-03 The Regents Of The University Of California Enhancing the cutaneous penetration of pharmacologically active agents
US5051260A (en) 1987-07-16 1991-09-24 The Regents Of The University Of California Method and composition for enhancing the cutaneous penetration of pharmacologically active agents
US5011681A (en) * 1989-10-11 1991-04-30 Richardson-Vicks, Inc. Facial cleansing compositions
DE4041118C2 (en) * 1990-12-21 2000-01-13 Henkel Kgaa Wax emulsion and its uses
US5989536A (en) * 1993-07-03 1999-11-23 The Procter & Gamble Company Personal cleansing compositions containing alkoxylated ether and cationic ammonium salt for deposition of active agent upon the skin
EP0714283B1 (en) 1993-07-03 1999-05-12 The Procter & Gamble Company Personal cleansing compositions
EP0716088B1 (en) * 1994-06-23 2004-02-18 Sumitomo Chemical Company, Limited Process for producing 2-(tetrazol-5-yl)-4-oxo-4h-benzopyrans
US5653970A (en) * 1994-12-08 1997-08-05 Lever Brothers Company, Division Of Conopco, Inc. Personal product compositions comprising heteroatom containing alkyl aldonamide compounds
US5607980A (en) * 1995-07-24 1997-03-04 The Procter & Gamble Company Topical compositions having improved skin feel
US5902805A (en) * 1996-04-22 1999-05-11 L'oreal Method for treatment of acne and/or the effects of ageing using HMG-coenzyme A-reductase inhibitor and compositions for performing the same
GB9612067D0 (en) * 1996-06-10 1996-08-14 Smithkline Beecham Plc Composition

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1993025650A1 (en) * 1992-06-16 1993-12-23 Henkel Corporation Viscosity-adjusted surfactant concentrate compositions
DE4408228A1 (en) * 1994-03-11 1995-09-14 Henkel Kgaa Low viscosity aqueous concentrate of betaine surfactants
US5429815A (en) * 1994-04-11 1995-07-04 Chesebrough-Pond's Usa Co., Division Of Conopco, Inc. Stable single-phase self-foaming cleanser
WO1995031962A1 (en) * 1994-05-20 1995-11-30 Gojo Industries, Inc. Antimicrobial cleaning composition containing chlorhexidine, anamphoteric and an alkylpolyglucoside
WO1996002225A1 (en) * 1994-07-19 1996-02-01 Unilever Plc Detergent composition
DE4435495A1 (en) * 1994-10-04 1996-04-11 Henkel Kgaa Pumpable aqueous surfactant concentrates
DE19504914C1 (en) * 1995-02-15 1995-11-16 Goldwell Gmbh Hair washing agent giving gloss and body, and easy combing

Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6998372B2 (en) 2001-08-16 2006-02-14 J&J Consumer Companies, Inc. Moisturizing detergent compositions
EP1975224A1 (en) * 2007-03-30 2008-10-01 Johnson & Johnson Consumer France SAS Mild, foaming cleansing composition
EP1997537A3 (en) * 2007-05-23 2012-02-01 Coty Prestige Lancaster Group GmbH Cosmetic skin cleaning product
EP2378872A4 (en) * 2008-12-18 2012-05-16 B Eugene Guthery Acne vulgaris treatment regimen
EP2378872A1 (en) * 2008-12-18 2011-10-26 B. Eugene Guthery Acne vulgaris treatment regimen
CN102985062A (en) * 2010-07-19 2013-03-20 高露洁-棕榄公司 Cleansing composition with decyl and coco glucosides
WO2012011892A1 (en) * 2010-07-19 2012-01-26 Colgate-Palmolive Company Cleansing composition with decyl and coco glucosides
US8877184B2 (en) 2010-07-19 2014-11-04 Colgate-Palmolive Company Cleaning composition with decyl and coco glucosides
RU2555356C2 (en) * 2010-07-19 2015-07-10 Колгейт-Палмолив Компани Detergent composition with decyl and coco glucosides
US9504635B2 (en) 2010-07-19 2016-11-29 Colgate-Palmolive Company Composition containing 4-oxovaleric acid and leuconostoc/radish root ferment filtrat
WO2016028177A1 (en) * 2014-08-21 2016-02-25 Uniwersytet Przyrodniczy W Poznaniu Liquid biostimulator increasing resistance of agricultural plants to stress conditions
WO2016037853A1 (en) * 2014-09-11 2016-03-17 Bode Chemie Gmbh Tuberculocidal disinfectant
RU2697082C2 (en) * 2014-09-11 2019-08-12 Боде Хеми Гмбх Disinfectant, destroying mycobacterium tuberculosis
WO2019212711A1 (en) * 2018-04-30 2019-11-07 L'oreal Gentle cleanser compositions
US11246815B2 (en) 2018-04-30 2022-02-15 L'oreal Gentle cleanser compositions

Also Published As

Publication number Publication date
MY124104A (en) 2006-06-30
CA2257810C (en) 2008-08-12
CY2506B1 (en) 2005-12-23
CZ293773B6 (en) 2004-07-14
GB9612067D0 (en) 1996-08-14
BR9709774A (en) 1999-08-10
PT906086E (en) 2003-12-31
DE69723979T2 (en) 2004-07-22
UA57023C2 (en) 2003-06-16
HUP0001821A3 (en) 2003-04-28
ZA975062B (en) 1998-08-12
US7179771B1 (en) 2007-02-20
NZ332864A (en) 2000-07-28
ATE246485T1 (en) 2003-08-15
NO985638L (en) 1998-12-03
HU226084B1 (en) 2008-04-28
EP0906086B1 (en) 2003-08-06
AU3033097A (en) 1998-01-07
SI0906086T1 (en) 2003-12-31
US6162774A (en) 2000-12-19
TW460294B (en) 2001-10-21
CZ407198A3 (en) 1999-05-12
JP2000512636A (en) 2000-09-26
EP0906086A1 (en) 1999-04-07
US6486106B1 (en) 2002-11-26
HK1016875A1 (en) 1999-11-12
EA199801001A1 (en) 1999-06-24
AR007542A1 (en) 1999-11-10
PL330603A1 (en) 1999-05-24
DE69723979D1 (en) 2003-09-11
DK0906086T3 (en) 2003-11-10
NO985638D0 (en) 1998-12-03
CN1121211C (en) 2003-09-17
AU720020B2 (en) 2000-05-18
CA2257810A1 (en) 1997-12-18
US20030118540A1 (en) 2003-06-26
KR20000016515A (en) 2000-03-25
PL186808B1 (en) 2004-02-27
ES2206714T3 (en) 2004-05-16
CN1221334A (en) 1999-06-30
NO314218B1 (en) 2003-02-17
HUP0001821A2 (en) 2000-11-28
EA001573B1 (en) 2001-06-25
SK168798A3 (en) 1999-05-07
SK284219B6 (en) 2004-11-03

Similar Documents

Publication Publication Date Title
US6162774A (en) Skin wash composition
US6224886B1 (en) Skin wash compositions comprising triclocarban and surfactants
US6323166B1 (en) Shampoo compositions
CZ219396A3 (en) Aqueous topic preparation
EP0500946B1 (en) Detergent composition
CA2151252A1 (en) Reduced alcohol mouthwash antiseptic and antiseptic preparations
EP1295593A1 (en) Skin cleanser containing anti-aging active
EP0965322B1 (en) Hair cleansing composition and personal cleansing composition with low skin irritancy
US5994280A (en) Cleansing compositions comprising an anionic surfactant and amphoteric surfactant mixture
US5100656A (en) Preserved hair and body treatment compositions and use of a preservative combination
KR102334446B1 (en) Transparent cosmetic composition for cleansing
JP2001131026A (en) Cosmetic for scalp and hair
KR100789686B1 (en) Detergent composition
DE19520859A1 (en) Use of a betaine ester and alpha-hydroxy acid-containing preparation for the care of the skin as well as new skin care products
EP1557161A1 (en) Method for cleansing sensitive skin using an alkanolamine
JP2001131025A (en) Cosmetic for scalp and hair
JPH05112442A (en) External preparation of skin
JPH03281700A (en) Lowly irritating detergent composition

Legal Events

Date Code Title Description
WWE Wipo information: entry into national phase

Ref document number: 97195350.3

Country of ref document: CN

AK Designated states

Kind code of ref document: A1

Designated state(s): AL AM AT AU AZ BA BB BG BR BY CA CH CN CU CZ DE DK EE ES FI GB GE GH HU IL IS JP KE KG KP KR KZ LC LK LR LS LT LU LV MD MG MK MN MW MX NO NZ PL PT RO RU SD SE SG SI SK TJ TM TR TT UA UG US UZ VN YU AM AZ BY KG KZ MD RU TJ TM

AL Designated countries for regional patents

Kind code of ref document: A1

Designated state(s): GH KE LS MW SD SZ UG AT BE CH DE DK ES FI FR GB GR IE IT LU MC NL PT SE BF

CFP Corrected version of a pamphlet front page
CR1 Correction of entry in section i

Free format text: PAT.BUL.54/97 UNDER INID (54) "IPC", REPLACE THE EXISTING TEXT BY "A61K 7/48, 7/50", AND UNDER INID (54) "TITLE", REPLACE THE EXISTING TEXT BY "SKIN WASH COMPOSITION"

DFPE Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed before 20040101)
CFP Corrected version of a pamphlet front page
CR1 Correction of entry in section i

Free format text: PAT. BUL. 54/97 UNDER (51) REPLACE "NOT CLASSIFIED" BY "A61K 7/48, 7/50" AND UNDER (54) THE TITLE IN ENGLISH SHOULD READ "SKIN WASH COMPOSITION"

WWE Wipo information: entry into national phase

Ref document number: 332864

Country of ref document: NZ

WWE Wipo information: entry into national phase

Ref document number: 1997925065

Country of ref document: EP

WWE Wipo information: entry into national phase

Ref document number: 09194383

Country of ref document: US

ENP Entry into the national phase

Ref document number: 2257810

Country of ref document: CA

Ref document number: 2257810

Country of ref document: CA

Kind code of ref document: A

WWE Wipo information: entry into national phase

Ref document number: 168798

Country of ref document: SK

WWE Wipo information: entry into national phase

Ref document number: PA/A/1998/010450

Country of ref document: MX

WWE Wipo information: entry into national phase

Ref document number: 1019980710102

Country of ref document: KR

Ref document number: PV1998-4071

Country of ref document: CZ

Ref document number: 199801001

Country of ref document: EA

121 Ep: the epo has been informed by wipo that ep was designated in this application
WWP Wipo information: published in national office

Ref document number: 1997925065

Country of ref document: EP

REG Reference to national code

Ref country code: DE

Ref legal event code: 8642

WWP Wipo information: published in national office

Ref document number: PV1998-4071

Country of ref document: CZ

WWP Wipo information: published in national office

Ref document number: 1019980710102

Country of ref document: KR

WWR Wipo information: refused in national office

Ref document number: 1019980710102

Country of ref document: KR

WWG Wipo information: grant in national office

Ref document number: 1997925065

Country of ref document: EP

WWG Wipo information: grant in national office

Ref document number: PV1998-4071

Country of ref document: CZ