EP0711144A1 - Composition cosmetique contenant des acides - Google Patents

Composition cosmetique contenant des acides

Info

Publication number
EP0711144A1
EP0711144A1 EP94925390A EP94925390A EP0711144A1 EP 0711144 A1 EP0711144 A1 EP 0711144A1 EP 94925390 A EP94925390 A EP 94925390A EP 94925390 A EP94925390 A EP 94925390A EP 0711144 A1 EP0711144 A1 EP 0711144A1
Authority
EP
European Patent Office
Prior art keywords
acid
skin
alpha hydroxy
composition
composition according
Prior art date
Legal status (The legal status 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 status listed.)
Withdrawn
Application number
EP94925390A
Other languages
German (de)
English (en)
Inventor
John Bartolone
Anthoney Vincent Rawlings
Robert Sabin
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Unilever PLC
Unilever NV
Original Assignee
Unilever PLC
Unilever NV
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 filed Critical Unilever PLC
Publication of EP0711144A1 publication Critical patent/EP0711144A1/fr
Withdrawn legal-status Critical Current

Links

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
    • A61Q19/08—Anti-ageing preparations
    • 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
    • A61K8/40—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
    • 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
    • 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
    • A61K2800/51—Chelating agents

Definitions

  • the invention relates to skin treatment compositions containing an alpha hydroxy acid or an ester or a salt thereof in combination with specific chelating agents.
  • Alpha hydroxy acids are emerging as accepted ingredients for improving the appearance of dry, flaky, wrinkled, aged, photodamaged skin and for treating various disorders o f skin, e.g., hyperkeratosis, ichthyosis, skin blemishes, acne, warts, herpes, psoriasis, eczema, pruritis. It is believed that alpha hydroxy acids act, at least in part, through stimulating the desquamation of outer corneocytes of stratum corneum. Unfortunately, the use of alpha hydroxy acids, particularly those containing eight or more carbon atoms, may be accompanied by an unpleasant sensory perception, e.g., stinging, and occasionally, an irritation of the skin. Therefore, it has been necessary to minimize the concentration of alpha hydroxy acids in skin treatment compositions, even though generally, the higher the concentration of the alpha hydroxy acid the better is the effect with regard to eliminating or preventing skin dryness, aging, or skin disorders.
  • EDTA ethylene diamine tetraacetic acid
  • Some chelating agents such as EDTA (ethylene diamine tetraacetic acid)
  • EDTA ethylene diamine tetraacetic acid
  • EDTA was included in prior art compositions at minute concentrations (i.e., not greater than 0.1%) as a preservative.
  • Prior art does not envision that the use of EDTA or other strong zinc and/or magnesium chelators in an effective amount with an alpha hydroxy acid may result in substantial improvement of the acid's activity, i.e., prior art does not envision synergistic combinations of a specific class of chelating agents and alpha hydroxy acids taught by the present invention.
  • a skin treatment composition containing an alpha hydroxy acid, or derivatives thereof, in combination with an ingredient which enhances the activity of the acid.
  • the invention includes skin treatment compositions containing an alpha hydroxy acid, or their derivatives (salts or esters) (hereafter called collectively "alpha hydroxy acid”) as a skin benefit ingredient.
  • the product according to the invention further includes a chelating agent, selected from specific classes of chelating agents, as an activity enhancer for the alpha hydroxy acid.
  • the chelating agent suitable for use in the present invention is selected from chelators which have high affinity with zinc and/or magnesium ions.
  • the presence of the activity enhancer in the inventive product substantially improves the performance of an alpha hydroxy acid, i.e., the activity enhancer substantially increases the ability of an alpha hydroxy acid to release corneocytes from stratum corneum.
  • the activity enhancer has no or little effect on improving skin benefit when used alone; it is only when combined wiith an alpha hydroxy acid that a substantial increase in skin benefit is realized.
  • the present invention is based, at least in part, on the discovery of synergistic interaction between alpha hydroxy acids and certain chelating agents.
  • the chelating agent is used in conjunction with longer chain alpha hydroxy acids (e.g., those containing at least 8 carbon atoms and, preferably, 10 or more carbon atoms) in order to attain an even more beneficial synergistic combination.
  • longer chain alpha hydroxy acids e.g., those containing at least 8 carbon atoms and, preferably, 10 or more carbon atoms
  • the performance of the compositions is substantially improved.
  • lower levels of an alpha hydroxy acid may be included in the composition containing the chelating agent to equal the performance of a similar formulation without the chelating agent, in order to minimize adverse reactions, such as skin irritation and stinging sensation.
  • the present invention also includes a method of improving or preventing the appearance of wrinkled, flaky, aged, photodamaged skin and treating skin disorders, which method includes applying to the skin a composition containing an alpha hydroxy acid and an activity enhancing amount of a chelating agent which has high affinity with zinc and/or magnesium ions.
  • compositions of the invention are intended for topical application to mammalian skin which is already in dry, flaky, wrinkled, aged, photodamaged condition or which suffers from a skin disorder, or, in the alternative, the inventive compositions may be applied prophylactically to normal healthy skin to prevent or reduce the deteriorative changes.
  • inventive compositions contain, as a first essential ingredient, a skin benefit agent selected from the group consisting of an alpha hydroxy acid, a salt of an alpha hydroxy acid, an ester of an alpha hydroxy acid, and mixtures thereof. All the above listed suitable skin benefit ingredients are collectively termed herein "alpha hydroxy acid.”
  • the alpha hydroxy acid or its ester has the following structure:
  • R- and R 2 are H, alkyl, aralkyl or aryl group of saturated or unsaturated, isomeric or non-isomeric, straight or branched chain or cyclic form, having 1 to 30 carbon atoms, and in addition R 2 may carry F, Cl, Br, I, N, S, OH, CHO, COOH and alkoxy group having 1 to 9 carbon atoms.
  • the alpha hydroxy acids may be present as a free acid or an ester form, or in a salt form with an organic base or an inorganic alkali.
  • R_ and R 2 include methyl, ethyl, propyi, isopropyl, butyl, pentyl, octyl, lauryl, stearyl, benzyl and phenyl, etc. ,
  • alphahydroxy acids include but are not limited to: alpha hydroxy acetic acid (also known as “glycolic acid”) alpha hydroxypropionic acid (also known as “lactic acid”) alpha hydroxytetranoic acid alpha hydroxyhexanoic acid alpha hydroxyoctanoic acid (also known as “alpha hydroxy caprylic acid”) alpha hydroxynonanoic acid alpha hydroxydecanoic acid alpha hydroxyundecanoic acid alpha hydroxydodecanoic acid (also known as "alpha hydroxy lauric acid”) alpha hydroxytetradecanoic acid alpha hydroxyhexadecanoic acid
  • esters of alpha hydroxy acids include but are not limited to:
  • Suitable salts of alpha hydroxy acids include but are not limited to sodium, potassium, ammonium, triethanolamine, calcium, lithium salts.
  • the salts may be obtained commercially or they may be prepared by methods known in the art, e.g., neutralizing an alpha hydroxy acid with a suitable base, such as hydroxide bases of ammonium, potassium, sodium.
  • a mixture of alpha hydroxy acids is employed in the compositions according to the invention.
  • the optimum performance is attained when a mixture of lactic acid, alpha hydroxy octanoic acid and alpha hydroxy lauric acid is employed.
  • inventive compositions contain the L-form of an alpha hydroxy acid.
  • Preferred compositions according to the invention contain at least 60% of an alpha hydroxy acid in L-configuration, by weight of total alpha hydroxy acid.
  • the inventive compositions contain from 60% to more than 99%, most preferably more than 99% of alpha hydroxy acids by weight of total hydroxy acids in the composition is in the L-form.
  • the total amount of alpha hydroxy acid in the inventive compositions ranges from 0.001% to 70%, preferably from 0.1% to 20%, and most preferably from 1% to 10% by weight of the composition, in order to attain maximum performance at optimal cost.
  • the total concentration of alpha hydroxy acids in the inventive compositions is at least 0.1% by weight of the composition.
  • the second essential ingredient of inventive compositions is a chelating agent.
  • Chelating agents included in inventive compositions have a high affinity with zinc and/or magnesium ions.
  • the chelating agent suitable for inclusion in inventive compositions is selected from the group consisting of chelating agents having an affinity with zinc ion of greater than 9.2, chelating agents having an affinity with magnesium ion of greater than 1.9, and mixtures thereof.
  • the affinity of a chelating agent for magnesium and/or zinc ions may be calculated as follows:
  • a chelator is characterized by the pK values and the absolute stability constant of its complex with a given metal ion. This allows the apparent stability constants to be calculated.
  • the chelate formation constant or stability constant is a .measure of the stability of the various chelator-metal complexes and quantifies the affinity of the metal for the chelator.
  • Log K values are contained in Critical Stability Constants, Volume 1: Amino Acids, Arthur E. Martell and Robert M. Smith (1974) , Plenum Press, New York.
  • the values for Log K were typically at 25°C and 0.1M ionic strength.
  • Log K values were normalized (adjusted for pH 7.4) to permit comparison of chelators by using the following formula obtained from Fluka BioChemika, "Basics for Biochemistry 'MicroSelect' " page 31 (1988), which may be obtained from Fluka Chemical Corporation, 980 South Second Street, Ronkonkoma, New York 11779.
  • log Kj at pH 7.4 must be calculated for magnesium and zinc ions. If log Kj for zinc ion is greater than 9.2 and/or log K_ for magnesium ion is greater than 1.9, the chelator is suitable for use in inventive compositions.
  • Suitable chelating agents may be selected from (among others) aminocarboxylic acids or salts thereof, polyphosphoric acids or salts thereof, diphosphonic acids, salts of diphosphonic acids, tertiary amines, aminophosphonic acids, iminodiacetic acid derivatives, azines, hydroxyquinolines, and amino acid esters as long as the chelating agent has the affinity with zinc ion of greater than 9.2 and/or the affinity with magnesium ion of greater than 1.9.
  • Suitable chelating agents include but are not limited to ethylene diamine tetraacetic acid, a salt of ethylene diamine tetraacetic acid, sodium pyrophosphate, sodium tripolyphosphate , 8 -hydroxyquinoline ,
  • the most preferred chelating agents according to the present invention are EDTA and/or pyrophosphate, and/or 8- hydroxy quinoline due to their ready availability, excellent performance, relatively low cost, and safety in use.
  • chelating agents other than the ones listed above, may be employed in the inventive compositions as long as the chelating agent has the affinity with zinc ion of greater than 9.2 and/or the affinity with magnesium ion of greater than 1.9.
  • the chelating agent is employed in the inventive compositions in the amount effective to enhance the activity of an alpha hydroxy acid.
  • the precise amount will depend on the particular chelating agent and alpha hydroxy acid included in the inventive compositions.
  • the amount is greater than 0.1%, preferably at least 0.2% by weight of the composition, most preferably in the range of from 0.2% to 2% to attain maximum performance at optimal cost.
  • the skin treatment composition of the invention also includes a therapeutically acceptable vehicle or a carrier which is inert, usually an ingredient present in highest amounts, and functioning to deliver active or performance ingredients.
  • a therapeutically acceptable vehicle or a carrier which is inert, usually an ingredient present in highest amounts, and functioning to deliver active or performance ingredients.
  • the amount of vehicle may suitably range from 2 to 99%, preferably from 5 to 80%, most preferably from 25 to 80%, by weight of the total compositions.
  • Surfactants which are also sometimes designated as emulsifiers, may be incorporated into the cosmetic compositions of the present invention.
  • Surfactants can suitably comprise anywhere from 0.5 to 30%, preferably from 1 to 15% by weight of the total composition.
  • Surfactants may be cationic, nonionic, anionic, or amphoteric in nature and combinations thereof may be employed.
  • Illustrative of the nonionic surfactants are alkoxylated compounds based upon fatty alcohols, fatty acids and sorbitan. These materials are available, for instance, from the Shell Chemical Company under the "Neodol" designation. Copolymers of polyoxypropylene- polyoxyethylene, available under the Pluronic trademark sold by the BASF Corporation, are sometimes also useful. Alkyl polyglycosides available from the Henkel Corporation similarly can be utilized for the purposes of this invention.
  • Anionic-type surfactants may include fatty acid soaps (polyglyceryl oleates) , sodium lauryl sulphate, sodium lauryl ether sulphate, alkyl benzene sulphonate, mono and dialkyl acid phosphates and sodium fatty acyl isethionate.
  • Amphoteric surfactants include such materials as dialkylamine oxide and various types of betaines (such as cocoamido propyl betaine) .
  • Emollients are often incorporated into cosmetic compositions of the present invention. Levels of such emollients may suitably range from 0.5 to 50%, preferably between 5 and 30% by weight of the total composition. Emollients may be classified under such general chemical categories as esters, fatty acids and alcohols, polyols and hydrocarbons.
  • Esters may be mono- or di-esters.
  • Acceptable examples of fatty di-esters include dibutyl adipate, diethyl sebacate, diisopropyl dimerate, and dioctyl succinate.
  • Acceptable branched chain fatty esters include isostearyl neopentanoate, 2-ethyl-hexyl myristate, isopropyl stearate and isostearyl palmitate.
  • Acceptable tribasic acid esters include triisopropyl trilinoleate and trilauryl citrate.
  • Acceptable straight chain fatty esters include cetyl octanoate lauryl palmitate, myristyl lactate, oleyl erucate and stearyl oleate.
  • Preferred esters include coco- caprylate/caprate (a blend of coco-caprylate and coco- caprate) , propylene glycol myristyl ether acetate, diisopropyl adipate and cetyl octanoate.
  • Suitable fatty alcohols and acids include those compounds having from 10 to 20 carbon atoms. Especially preferred are such compounds such as cetyl, myristyl, palmitic and stearyl alcohols and acids.
  • polyols which may serve as emollients are linear and branched chain alkyl polyhydroxyl compounds.
  • propylene glycol, sorbitol and glycerin are preferred.
  • polymeric polyols such as polypropylene glycol and polyethylene glycol.
  • hydrocarbons which may serve as emollients are those having hydrocarbon chains anywhere from 12 to 30 carbon atoms. Specific examples include mineral oil, petroleum jelly, squalene and isoparaffins.
  • thickeners are also categories of functional ingredients within the cosmetic compositions of the present invention.
  • a thickener will usually be present in amounts anywhere from 0.1 to 20% by weight, preferably from 0.5 to 10% by weight of the composition.
  • Exemplary thickeners are cross-linked polyacrylate materials available under the trademark Carbopol from the B.F. Goodrich Company. Gums may be employed such as xanthan, carrageenan, gelatin, karaya, pectin and locust beans gum. Under certain circumstances, the thickening function may be accomplished by a material also serving as a silicone or emollient. For instance, silicone gums in excess of 10 centistokes and esters such as glycerol stearate have dual functionality.
  • Actives are defined as skin benefit agents other than emollients and other than ingredients that merely improve the physical characteristics of the composition. Although not limited to this category, general examples include sunscreens, tanning agents, other skin anti-wrinkling agents, and anti- acne agents.
  • a preferred optional active ingredient to be included in the inventive composition are ceramides which play an important role in the production and maintenance of the water permeability barrier of the skin.
  • ceramides and synthetic analogues thereof are disclosed in European Patent Application 534 286, European Patent application 282 816, European Patent Application 227 994, U.S. Patent 5,175,321, U.S. Patent 4,985,547, U.S. Patent 5,028,416, U.S. Patent 5,071,971, Japanese Patent Application 63192703, U.S. Patent 4,468,519, and U.S. Patent 4,950,688, all of which are incorporated by reference herein.
  • Ceramides or their synthetic analogues may be present in the inventive compositions at a level of from 0.00001 to 5%, preferably from 0.0001 to 1%, optimally from 0.01 to 0.5%.
  • lipids e.g., ceramides or phospholipids
  • carboxylic acids and sterols preferably is incorporated in inventive compositions.
  • inventive compositions e.g., ceramides or phospholipids
  • the combination is disclosed in greater detail in U.S. patent application 08/007,468 incorporated by reference herein.
  • Sunscreens include those materials commonly employed to block ultraviolet light.
  • Illustrative compounds are the derivatives of PABA, cinnamate and salicylate.
  • octyl methoxycinnamate and 2-hydroxy-4-methoxy benzophenone also known as oxybenzone
  • Octyl methoxycinnamate and 2-hydroxy-4-methoxy benzophenone are commercially available under the trademarks, Parsol MCX and Benzophenone-3, respectively.
  • the exact amount of sunscreen employed in the emulsions can vary depending upon the degree of protection desired from the sun's UV radiation.
  • Vitamins such as vitamins A, E, C, and D and their derivatives may also be included in the compositions of the present invention, especially preferred is vitamin A palmitate (retinyl palmitate) and vitamin E linoleate (tocopheryl linoleate) .
  • vitamin A palmitate retinyl palmitate
  • vitamin E linoleate tocopheryl linoleate
  • Other esters of vitamins A and E may also be utilized.
  • Suitable preservatives include alkyl esters of p-hydroxybenzoic acid, hydantoin derivatives, propionate salts, and a variety of quaternary ammonium compounds.
  • Particularly preferred preservatives of this invention are methyl paraben, propyl paraben, imidazolidinyl urea, sodium dehydroxyacetate and benzyl alcohol. Preservatives will usually be employed in amounts ranging from about 0.5% to 2% by weight of. the composition.
  • adjunct minor components may also be incorporated into the cosmetic compositions.
  • These ingredients may include colouring agents, opacifiers and perfumes. Amounts of these materials may range anywhere from 0.001 up to 20% by weight of the composition.
  • the corneocyte release assay was utilized in order to investigate the effect of alpha hydroxy acid (alone or in the presence of various chelators) on skin desquamation.
  • Split thickness cadaver skin was washed for 15 minutes in phosphate-buffered saline to remove any loosely held corneocytes. Thereafter, 4mm punch biopsies were obtained and placed into 1.5ml microfuge tubes (2 biopsies per tube) containing 400 ⁇ l of the test solution consisting of 0.1M Tris-HCI (pH 7.4 with triethanolamine) , a chelator, 0.02%- sodium azide and an alpha hydroxy acid. Controls utilized the same solution in the absence of any chelators.
  • the chelators (EDTA, pyrophosphate, EGTA and 8-hydroxy quinoline) in the absence of any alpha hydroxy acids did not stimulate any release of corneocytes.
  • Examples 1-3 and 5 are within the scope of the invention (as shown in Table 1, EDTA, pyrophosphate and 8- hydroxyquinoline satisfy the requirements for Mg and/or Zn binding affinity) .
  • Examples 1-3 and 5 demonstrate synergistic interaction between chelators which have high affinity with Mg 2+ and/or Z N 2+ ions and alpha hydroxy acids.
  • Example 5 demonstrates a particularly strong synergy between chelators within the scope of the invention and longer chain (e.g., C 12 ) alpha hydroxy acids.
  • Comparative Example 4 which is not within the scope of the invention, demonstrates that chelators which do not have the affinity with magnesium ion of greater than 1.9 and/or the affinity with zinc ion of greater than 9.2 do not significantly enhance the activity of an alpha hydroxy acid.
  • composition for topical application to skin was prepared:
  • composition for topical application to skin was prepared:
  • composition for topical application to skin was prepared:
  • Increased skin flexibility corresponds to a decrease or absence in skin flakiness and dryness.
  • Skin flexibility is measured in vitro by stratum corneum extensibility test.
  • the increase in keratinocyte differentiation accompanies abnormal conditions of stratum corneum, such as skin disorders and skin dryness.
  • Keratinocyte proliferation decreases with age.
  • the increase in keratinocyte proliferation is beneficial to counteract skin aging (i.e., wrinkles, thickness, elasticity, and repair) .

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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)
  • Dermatology (AREA)
  • Gerontology & Geriatric Medicine (AREA)
  • Emergency Medicine (AREA)
  • Cosmetics (AREA)

Abstract

L'invention concerne une composition de traitement de la peau contenant un ingrédient bénéfique pour la peau choisi dans le groupe comprenant un acide hydroxylique alpha, un sel ou un ester de ce dernier, des mélanges de ces derniers ainsi qu'un agent de chélation. Les agents de chélation appropriés présentent une grande affinité avec les ions de zinc et/ou de magnésium. Plus précisément, l'agent de chélation est choisi dans le groupe d'agents présentant une grande affinité avec les ions de zinc de plus de 9,2, ainsi qu'avec les ions de magnésium de plus de 1,9, et des mélanges de ces derniers.
EP94925390A 1993-07-26 1994-07-23 Composition cosmetique contenant des acides Withdrawn EP0711144A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US9687893A 1993-07-26 1993-07-26
US96878 1993-07-26
PCT/EP1994/002456 WO1995003032A1 (fr) 1993-07-26 1994-07-23 Composition cosmetique contenant des acides

Publications (1)

Publication Number Publication Date
EP0711144A1 true EP0711144A1 (fr) 1996-05-15

Family

ID=22259528

Family Applications (1)

Application Number Title Priority Date Filing Date
EP94925390A Withdrawn EP0711144A1 (fr) 1993-07-26 1994-07-23 Composition cosmetique contenant des acides

Country Status (4)

Country Link
EP (1) EP0711144A1 (fr)
AU (1) AU7532794A (fr)
CA (1) CA2161525A1 (fr)
WO (1) WO1995003032A1 (fr)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA2143515A1 (fr) * 1994-03-22 1995-09-23 Prakash Parab Methode permettant d'accroitre le rythme de penetration dans la peau de l'acide lactique par l'utilisation de l'enantiomere l
AU3081395A (en) * 1994-07-22 1996-02-22 Coletica Lipophilic hydroxylated acid, cosmetic and pharmaceutical use thereof and method for preparing same
US5720963A (en) * 1994-08-26 1998-02-24 Mary Kay Inc. Barrier disruption treatments for structurally deteriorated skin
DE19518815A1 (de) * 1995-05-23 1996-11-28 Beiersdorf Ag Kosmetische oder dermatologische Zubereitungen mit einem Gehalt an alpha-Hydroxyfettsäuren
US6159479A (en) * 1997-09-16 2000-12-12 L'oreal Hydrous salicylic acid solutions
US7846919B2 (en) * 1998-02-10 2010-12-07 Dermex Pharmaceuticals, Llc Chelated 8-hydroxyquinoline and use thereof in a method of treating epithelial lesions

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1993009213A1 (fr) * 1991-11-07 1993-05-13 Gycor International Ltd. Agent de nettoyage et d'assainissement non toxique
EP0608433B1 (fr) * 1992-07-13 2004-05-19 Shiseido Company, Ltd. Composition de preparation dermatologique

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO9503032A1 *

Also Published As

Publication number Publication date
WO1995003032A1 (fr) 1995-02-02
CA2161525A1 (fr) 1995-02-02
AU7532794A (en) 1995-02-20

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