WO1997030690A1 - Traitement de la peau avec des esters de l'acide salicylique - Google Patents

Traitement de la peau avec des esters de l'acide salicylique Download PDF

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Publication number
WO1997030690A1
WO1997030690A1 PCT/EP1997/000386 EP9700386W WO9730690A1 WO 1997030690 A1 WO1997030690 A1 WO 1997030690A1 EP 9700386 W EP9700386 W EP 9700386W WO 9730690 A1 WO9730690 A1 WO 9730690A1
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WO
WIPO (PCT)
Prior art keywords
skin
group
alkyl
salicylate
chronoaging
Prior art date
Application number
PCT/EP1997/000386
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English (en)
Inventor
Angel Augusto Guerrero
Peter Ladislaus Dorogi
Thomas Charles Klepacky
Original Assignee
Unilever Plc
Unilever N.V.
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 N.V. filed Critical Unilever Plc
Priority to AU15964/97A priority Critical patent/AU1596497A/en
Publication of WO1997030690A1 publication Critical patent/WO1997030690A1/fr

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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
    • A61K8/37—Esters of carboxylic acids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/60—Salicylic acid; Derivatives thereof
    • A61K31/618—Salicylic acid; Derivatives thereof having the carboxyl group in position 1 esterified, e.g. salsalate
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/04—Dispersions; Emulsions
    • A61K8/06—Emulsions
    • A61K8/068—Microemulsions
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/007—Preparations for dry skin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/08—Anti-ageing preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/006—Antidandruff preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
    • A61Q17/04—Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations

Definitions

  • the present invention concerns methods of treating skin with compositions containing certain esters of salicylic acid and use of such esters in such compositions.
  • Dermatologic disorders include such conditions as acne, dry skin, dandruff, keratosis, pruritus, inflammatory dermatoses, eczema, psoriasis and tenia pedis (athlete's foot).
  • Chronoaging results in the thinning and general degradation of skin. As skin naturally ages, there is reduction in the cells and blood vessels that supply the skin. There is also a flattening of the dermal-epidermal junction which results in weaker mechanical resistance. Older individuals increasingly develop facial fine lines, wrinkles, leatheriness, yellowing, sagging, mottling (hyperpig entation) , age spots and the general signs of aging.
  • Extrinsic factors are primarily those caused by exposure to sun. Changes are most prominent in light skinned individuals who burn easily and tan poorly. The results of photodamage may be identical to those of aging except appearing at an accelerated rate. Wrinkling, yellowing, leatheriness, mottling and hyperpigmentation are all associated with sun damage. Most disturbing to many individuals is the wrinkling effect. It is a prime reminder of the disappearance of youth. As a result, there have been many reports of cosmetic treatments aimed at the elimination of wrinkles.
  • Ring alkylated salicylic acid has been reported in Japanese Patent 4036238 (Takasago Perfumery KK) for treatment of acne vulgaris.
  • dermatologic disorders such as acne, dry skin, dandruff, keratosis, pruritus, inflammatory dermatosis, eczema, psoriasis and tinea pedis.
  • Another object of the present invention is to provide a cosmetic treatment for chronoaging conditions including wrinkling and fine lines, leatheriness, yellowing, sagging, mottling (hyperpigmentation), age spots, thinning of the skin, loss of elasticity, loss of collagen and the general signs of aging.
  • Still another object of the present invention is to provide a cosmetic treatment against environmental abuse to skin including wrinkling and fine lines, yellowing, leatheriness, mottling and hyperpigmentation.
  • Yet another object of the present invention is to provide a treatment to improve the condition of skin with a composition and active that does not impart irritation.
  • R is a C n -C 30 alkyl or alkenyl radical.
  • the invention also encompasses the use of a salicylate ester as described above in a composition for topical application to the skin as an active for treating a skin condition selected from the group consisting of dermatologic disorders, chronoaging and environmental abuse.
  • R is a C n -C 30 alkyl or alkenyl radical.
  • Preferred are the C 12 -C 20 alkyl or alkenyl, optimally the C 13 alkyl or alkenyl esters of salicylic acid. The most preferred is tridecyl salicylate.
  • the ⁇ sent invention applies in particular for such derm ⁇ -logic disorders as a ne, dry skin, dandruff, kerat-sis, pruritus, inflammatory dermatitis, eczema, psoriasis and tinea pedis.
  • chronoaging it applies particularly for conditions involving wrinkling, fine lines, leatheriness, yellowing, sagging, hyperpigmentation, age spots, thinning of the skin, loss of elasticity, loss of collagen and/or general signs of aging.
  • Use of the present salicylate ester in skin care compositions for treating skin that has been subjected to environmental abuse is in particular beneficial in case of conditions exhibiting wrinkling, fine lines, leatheriness, yellowing, mottling and/or hyperpigmentation.
  • Safe and effective amounts of the C n -C 30 esters of salicylic acid are to be used within cosmetic compositions of the present invention.
  • the term "safe and effective amounts” are defined as any amount sufficient to significantly induce a positive modification in the condition to be treated, but low enough to avoid serious side effects (at a reasonable benefit/risk ratio) , within the scope of sound medical judgement.
  • the safe and effective amount of the salicylate esters will vary with the particular condition being treated, the age and physical condition of the person being treated, the severity of the condition, the duration of the treatment, the nature of concurrent treatment, the specific ester employed, the particular pharmaceutically-acceptable carrier utilized, and like factors in the knowledge and expertise of the attending specialist. Generally these amounts may range from 0.01 to 20%, preferably from 0.1 to 10%, more preferably from 1 to 8%, optimally from 2 to 6% by weight.
  • compositions of the present invention will 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 usually be in amounts which may range from 5 to 95%, preferably from 20 to 70%, optimally between 35 and 60% by weight.
  • relatively volatile solvents may also serve as carriers within compositions of the present invention.
  • monohydric C j -C 3 alkanols include 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.
  • Emollient materials may also serve as pharmaceutically acceptable carriers. These may be in the form of silicone oils and synthetic esters. Amounts of the emollients may range anywhere from 0.1 to 30%, preferably between 1 and 20% by weight.
  • Silicone oils may be divided into the volatile and non-volatile variety.
  • 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 less than about 5 centistokes at 25°C while cyclic materials typically have viscosities of less than about 10 centistokes.
  • Nonvolatile silicone oils useful as an emollient material include polyalkyl siloxanes, polyalkylaryl siloxanes and polyether siloxane copolymers.
  • the essentially non-volatile polya.- yl siloxanes useful herein include, for example, polydimethyl siloxanes with viscosities of from about 5 to about 100,000 centistokes at 25°C.
  • the preferred non-volatile emollients useful in the present compositions are the polydimethyl siloxanes having viscosities from about 10 to about 400 centistokes at 25°C.
  • ester emollients are:
  • Alkenyl or alkyl esters of fatty acids having 10 to 20 carbon atoms examples thereof include isoarachidyl neopentanoate, isononyl isonanonoate, oleyl myristate, oleyl stearate, and oleyl oleate.
  • Ether-esters such as fatty acid esters of ethoxylated fatty alcohols.
  • 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 esters, 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 are satisfactory polyhydric alcohol esters.
  • Wax esters such as beeswax, spermaceti, myristyl myristate, stearyl stearate and arachidyl behenate.
  • Sterols esters of which cholesterol fatty acid esters are examples thereof.
  • esters are isoarachidyl neopentanoate and isononyl isononanoate.
  • Fatty acids having from 10 to 30 carbon atoms may also be included as pharmaceutically acceptable carriers for compositions of this invention.
  • Illustrative of this category are pelargonic, lauric, myristic, palmitic, stearic, isostearic, hydroxystearic, oleic, linoleic, ricinoleic, arachidic, behenic and erucic acids.
  • Humectants of the polyhydric alcohol-type may also be employed as pharmaceutically acceptable carriers in compositions of this invention.
  • the humectant aids in increasing the effectiveness of the emollient, reduces scaling, stimulates removal of built-up scale and improves skin feel.
  • Typical polyhydric 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, 1,2, 6-hexanetriol, 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 compositions according to the present invention.
  • Typical thickeners include crosslinked acrylates (e.g. Carbopol 982®), hydrophobically-modified acrylates (e.g. Carbopol 1382®), cellulosic derive ives and natural gums.
  • useful cellulosic deri" stives are sodium carboxymethylcellulose, hydroxypropyl methylcellulose, hydroxypropyl cellulose, hydroxyethyl cellulose, ethyl cellulose and hydroxymethyl cellulose.
  • Natural gums suitable for the present invention include guar, xanthan, sclerotiu , carrageenan, pectin and combinations of these gums.
  • 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.
  • water, solvents, silicones, esters, fatty acids, humectants and/or thickeners will constitute the pharmaceutically acceptable carrier in amounts from 1 to 99.9%, preferably from 80 to 99% by weight.
  • Cosmetic compositions of the present invention may be in any form. These forms may include emulsified systems such as lotions and creams, microemulsions, roll-on formulations, mousses, ointments (hydrophilic and hydrophobic) , aerosol and non-aerosol sprays and pad- applied formulations.
  • emulsified systems such as lotions and creams, microemulsions, roll-on formulations, mousses, ointments (hydrophilic and hydrophobic) , aerosol and non-aerosol sprays and pad- applied formulations.
  • Surfactants may also be present in cosmetic compositions of the present invention.
  • total concentration of the surfactant will typically range from 0.1 to 40%, preferably from 1 to 20%, optimally from 1 to 5% by weight of the composition.
  • the surfactant may be selected from the group consisting of anionic, nonionic, cationic and amphoteric actives.
  • 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 10 alkyl 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- C 8 -C 20 fatty acids; block copolymers (ethylene oxide/propylene oxide); and polyoxyethylene sorbitan as well as combinations thereof.
  • Alkyl polyglycosides and saccharide 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, C 8 -C 20 acyl isethionates, acyl glutamates, C 8 -C 20 alkyl ether phosphates and combinations thereof.
  • Sunscreen actives may also be included in compositions of the present invention. Particularly preferred are such materials as ethylhexyl p-methoxycinnamate, available as Parsol MCX, and benzophenone-3, also known as Oxybenzone.
  • Inorganic sunscreen actives may be employed such as microfine titanium dioxide, polyethylene and various other polymers. Amounts of the sunscreen agents will generally range from 0.1 to 30%, preferably from 2 to 20%, optimally from 4 to 10% by weight.
  • Preservatives can desirably be incorporated into the cosmetic compositions of this invention to protect against the growth of potentially harmful microorganisms.
  • Suitable traditional preservatives for compositions of this invention are 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.
  • preservatives are phenoxyethanol, methyl paraben, propyl paraben, imidazolidinyl urea, sodium dehydroacetate and benzyl alcohol.
  • the preserva ⁇ tives 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 also contain water-soluble vitamins.
  • water-soluble defines substances with a solubility of at least 0.1%, preferably at least 1%, optimally at least 5% by weight in water.
  • Illustrative water-soluble vitamins are Niacin, Vitamin B 6 , Vitamin B 6 , Vitamin C and Biotin.
  • One source for Vitamin C is a product sold under the trademark of Vitazyme C available from the Brooks Company.
  • Niacin, Vitamin B and Biotin are available from Roche Pharmaceuticals.
  • Total amount of vitamins in compositions according to the present invention may range from 0.001 to 1%, preferably from 0.01 to 0.6, optimally from 0.1 to 0.5% by weight.
  • Keratolytic agents such as C 2 -C 25 o-hydroxy alkanoic acids may also be incorporated into compositions of this invention. Illustrative of this group of materials are glycolic, lactic, ⁇ -hydroxyoctanoic acids and salts thereof.
  • the salts may be selected from alkalimetal, ammonium and alkyl or alkanolammonium counterions.
  • Levels of o-hydroxyalkanoic acids may range from 0.001 to 10%, preferably between 0.2 and 1%, optimally between 0.4 and 0.5% by weight.
  • Minor adjunct ingredients may also be present in the cosmetic compositions. Among them may be the water- insoluble vitamins such as Vitamin A Palmitate, Vitamin E Acetate and DL-panthenol.
  • Another adjunct ingredient can be that of an enzyme.
  • Particularly preferred is superoxide dismutase, commercially available as Biocell SOD from the Brooks Company, USA.
  • cosmetic compositions of the present invention may include ⁇ -glucan derived from oats, commercially available under the trademark Microat SF from Nurture Inc, Missoula, Montana.
  • 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.
  • the following sunscreen creme was prepared having a composition indicated under Table I.
  • Carbopol 1382® (2% solids) 8.000
  • a cre e was prepared having a composition described in Table II.
  • Carbopol 1382® (2% Solids) 18.000
  • the test panel was comprised of 45 female human volunteer subjects (21 using Example 1 and 24 using Example 2). Enrolled subjects had a facial acne grade of II (Pilsbury) or lower and no facial irritation beyond the specific acne lesions.
  • the investigator assessed the global facial irritation and acne condition of each subject.
  • the lighting conditions, fluorescent overhead lights in a fluorescent ring lamp with a diopter lens (as needed) were identical for each evaluation.
  • Each subject used either product twice daily (morning and evening) for twenty-eight days, recording all use on a diary form.
  • the investigator's global facial assessments of open lesions, closed lesions, papules, pustules, nodules and irritation were transferred via data entry from the original data sheets to computer. Analysis was conducted using the paired sample t-Test on the global mean scores within each product group and on the differences from baseline in global mean scores for a product vs. product comparison. Significance was assessed at the p 0.05 level (95% confidence) .
  • Example 2 Although the compositions of Example 1 and 2 vary slightly, the major difference is the presence of 4% tridecyl salicylate in Example 2. From the above study, it is evident that the tridecyl salicylate had a significant effect upon treating the conditions of acne while being nonirritating.
  • a microemulsion formulation according to the present invention is outlined under Table III.
  • a skin lotion (water in oil type) formulation according to the present invention is outlined under Table IV.
  • a skin cream (oil in water type) formulation according to the present invention is outlined under Table V.
  • An anhydrous serum formulation according to the present invention is outlined under Table VI.
  • a skin lotion (oil in water type) formulation according to the present invention is outlined under Table VII.
  • a protective skin lotion with sunscreen formulation according to the present invention is outlined under Table VIII.
  • the crepey skin protocol is a clinical visual assessment of forearm skin. This condition is associated with photoaged skin and reflects skin which takes on a sagging, rough, wrinkled appearance.
  • the clinical test is 12 weeks in duration and evaluates 2 different test formulations in a paired manner (one on each forearm) using 15 women with moderate forearm crepiness.
  • the study is conducted in a double blinded manner where neither the subject or clinical evaluator has knowledge of the test material being applied to the forearms. Only subjects with equivalent crepiness on both forearms are enrolled.
  • a directed-difference scale is used to quantitate any perceived difference between right and left treated forearms. If there is no perceivable difference between forearms a 0 is noted. In the event one forearm is better, the more improved forearm i ⁇ iven a score from 1 to 4 (smallest to greatest) where these values represent a difference level of improvement over the companion treated forearm. The forearm which is showing greater improvement will therefore attain a higher average absolute score.
  • Results of the clinical are provided in Table X. They show that the tridecyl salicylate formulation is superior to the vehicle. This is evident as the directed difference scores are in the negative direction favouring the tridecyl salicylate formulation. The only difference between the vehicle and experimental formulations is tridecyl salicylate. All other ingredients, pH, etc. are the same.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
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  • Epidemiology (AREA)
  • Dermatology (AREA)
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  • Pharmacology & Pharmacy (AREA)
  • Gerontology & Geriatric Medicine (AREA)
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  • Cosmetics (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

L'invention concerne une méthode pour traiter différentes atteintes de la peau, telles que les maladies dermiques, le vieillissement normal et les agressions de l'environnement. On utilise pour cela comme ingrédient actif des esters du type salicylate de C11-C30 alkyle non cyclique/C11-C30 alcényle non cyclique, en combinaison avec un vecteur acceptable sur le plan pharmaceutique. Le composé préféré est le salicylate de tridécyle.
PCT/EP1997/000386 1996-02-23 1997-01-23 Traitement de la peau avec des esters de l'acide salicylique WO1997030690A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU15964/97A AU1596497A (en) 1996-02-23 1997-01-23 Skin treatment with salicylic acid esters

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US1214196P 1996-02-23 1996-02-23
US60/012,141 1996-02-23

Publications (1)

Publication Number Publication Date
WO1997030690A1 true WO1997030690A1 (fr) 1997-08-28

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AR (1) AR014091A1 (fr)
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Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1998023257A1 (fr) * 1996-11-27 1998-06-04 Unilever Plc Procede pour reduire les matieres grasses produites par la peau
WO1998051274A1 (fr) * 1997-05-09 1998-11-19 Unilever Plc Compositions de cremes cosmetiques revitalisantes
EP0979644A1 (fr) * 1998-08-13 2000-02-16 Società Italo-Britannica L. Manetti-H. Roberts & C. S.p.A. Composition cosmétique déodorante ou hydratante
WO2000012059A1 (fr) * 1998-08-27 2000-03-09 The Procter & Gamble Company Attenuation de l'irritation liee aux compositions a base de vitamine b3
US6444647B1 (en) 1999-04-19 2002-09-03 The Procter & Gamble Company Skin care compositions containing combination of skin care actives
EP1262169A2 (fr) * 2001-05-29 2002-12-04 L'oreal Composition pour le traitement des signes cutanés du vieillissement
WO2004050045A1 (fr) * 2002-12-04 2004-06-17 Dow Corning Corporation Compositions de vesicules et de microemulsion d'huiles polaires organiques a base de tensioactifs silicone
WO2004073707A1 (fr) * 2003-02-19 2004-09-02 Unilever N.V. Composition topique contenant gallate d'alkyle ou hydroxybenzoate d'alkyle ou alkyloxy de phenol comme agent contre l'acne
JP2017528453A (ja) * 2014-09-26 2017-09-28 ディーエスエム アイピー アセッツ ビー．ブイ． Ｏ／ｗエマルジョン
WO2018177969A1 (fr) * 2017-03-31 2018-10-04 Dsm Ip Assets B.V. Procédé de protection de la peau humaine contre les dommages lors de l'exposition à la lumière bleue
WO2020052916A1 (fr) 2018-09-11 2020-03-19 Unilever N.V. Composition topique comprenant un isomérat de saccharide pour un équilibrage du microbiome

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0676194A2 (fr) * 1994-04-01 1995-10-11 Roussel Uclaf Compositions cosmétiques ou dermatologiques contenant un alpha-hydroxyacide de l'acide salicylique et un retinoide
EP0713696A1 (fr) * 1994-10-24 1996-05-29 L'oreal Produit pour application topique contenant une lipase et un precurseur d'hydroxyacide

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0676194A2 (fr) * 1994-04-01 1995-10-11 Roussel Uclaf Compositions cosmétiques ou dermatologiques contenant un alpha-hydroxyacide de l'acide salicylique et un retinoide
EP0713696A1 (fr) * 1994-10-24 1996-05-29 L'oreal Produit pour application topique contenant une lipase et un precurseur d'hydroxyacide

Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1998023257A1 (fr) * 1996-11-27 1998-06-04 Unilever Plc Procede pour reduire les matieres grasses produites par la peau
WO1998051274A1 (fr) * 1997-05-09 1998-11-19 Unilever Plc Compositions de cremes cosmetiques revitalisantes
EP0979644A1 (fr) * 1998-08-13 2000-02-16 Società Italo-Britannica L. Manetti-H. Roberts & C. S.p.A. Composition cosmétique déodorante ou hydratante
WO2000012059A1 (fr) * 1998-08-27 2000-03-09 The Procter & Gamble Company Attenuation de l'irritation liee aux compositions a base de vitamine b3
US6444647B1 (en) 1999-04-19 2002-09-03 The Procter & Gamble Company Skin care compositions containing combination of skin care actives
EP1262169A3 (fr) * 2001-05-29 2004-05-06 L'oreal Composition pour le traitement des signes cutanés du vieillissement
EP1262169A2 (fr) * 2001-05-29 2002-12-04 L'oreal Composition pour le traitement des signes cutanés du vieillissement
WO2004050045A1 (fr) * 2002-12-04 2004-06-17 Dow Corning Corporation Compositions de vesicules et de microemulsion d'huiles polaires organiques a base de tensioactifs silicone
WO2004073707A1 (fr) * 2003-02-19 2004-09-02 Unilever N.V. Composition topique contenant gallate d'alkyle ou hydroxybenzoate d'alkyle ou alkyloxy de phenol comme agent contre l'acne
JP2017528453A (ja) * 2014-09-26 2017-09-28 ディーエスエム アイピー アセッツ ビー．ブイ． Ｏ／ｗエマルジョン
WO2018177969A1 (fr) * 2017-03-31 2018-10-04 Dsm Ip Assets B.V. Procédé de protection de la peau humaine contre les dommages lors de l'exposition à la lumière bleue
CN110461304A (zh) * 2017-03-31 2019-11-15 帝斯曼知识产权资产管理有限公司 保护人皮肤抵抗蓝光暴露损伤的方法
CN110461304B (zh) * 2017-03-31 2022-11-11 帝斯曼知识产权资产管理有限公司 保护人皮肤抵抗蓝光暴露损伤的方法
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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