US3781417A - Light protection agent for cosmetic purposes - Google Patents

Light protection agent for cosmetic purposes Download PDF

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Publication number
US3781417A
US3781417A US00318998A US3781417DA US3781417A US 3781417 A US3781417 A US 3781417A US 00318998 A US00318998 A US 00318998A US 3781417D A US3781417D A US 3781417DA US 3781417 A US3781417 A US 3781417A
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US
United States
Prior art keywords
camphor
radiation
oil
methylbenzylidene
sunlight
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.)
Expired - Lifetime
Application number
US00318998A
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English (en)
Inventor
R Welters
H Russmann
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.)
Merck Patent GmbH
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Merck Patent GmbH
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Filing date
Publication date
Application filed by Merck Patent GmbH filed Critical Merck Patent GmbH
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Publication of US3781417A publication Critical patent/US3781417A/en
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Classifications

    • 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
    • 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
    • A61K8/35—Ketones, e.g. benzophenone
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
    • C07C49/657—Unsaturated compounds containing a keto groups being part of a ring containing six-membered aromatic rings
    • C07C49/683—Unsaturated compounds containing a keto groups being part of a ring containing six-membered aromatic rings having unsaturation outside the aromatic rings

Definitions

  • This invention relates to cosmetic compositions containing a UV absorbent.
  • a normal cosmetic light-protection agent should thus absorb radiation from the sunlight spectrum in the range of 285315 nm. as completely as possible, but should provide as complete a transmittance as possible of radiation of a longer wavelength.
  • 3-cinnamylidene-D,L- camphor is characterized by an excellent broad-band filter effect.
  • this invention relates to U.V.- absorbent-containing compositions adapted for cosmetic purposes containing at least one compound of Forumla I wherein R is p-tolyl or styryl, in mixture with a cosmetically acceptable carrier adapted for topical application to the human skin.
  • compositions whic additionally contain one or more other U.V. absorbents.
  • this invention relates to the use of one of the above-described agents for protection against an overdose of U.V. radiation of the range between 285 and 315 nm. and for the prevention of the associated burn manifestations of human skin known generally as sunburn and also to the use of such compositions for protection against light radiation in the range of from 285 to 380 nm.
  • the absorption maximum of the 3-(4-methylbenzylidene)-D,L-camphor on which the agents of this invention are based is approximately 299 nm., lying exactly centrally in the erythema producing zone, so that this range of radiation is covered symmetrically and completely by the absorption band. Furthermore, the solubility of this compound in the solvents customary is cosmetics satisfies even the strictest requirements.
  • solubility of 3 (4-methyl'benzylidene)-D,L-camphor in paraflin oil is 20% by weight at room temperature, which far exceeds the 10% by weight, which is generally considered the minimum limit of solubility.
  • 3-benzylidene-D,L-camphor for example, is soluble in the same solvent at room temperature only to the extent of 7.5%.
  • compositions of this invention containing 3-cinnamylidene-camphor can be employedespecially advantageously as broad-band filters. This can be seen from the transmittance of a 0.002% solution in isopropanol at various wavelengths.
  • the U.V. absorbing compounds of the compositions of this invention are very stable thermally and with respect to the eflects of light radiation. Thus, in a xenon test, after a 24-hour exposure no change in transmittance was observed. They are not decomposed in either acidic or alkaline reaction mediums. Their skin compatibility is good and no deleterious side-etiects have been observed.
  • U.V. absorbers can be produced in a conventional manner by condensing the sodium salt of camphor with the corresponding aromatic aldehydes, preferably in an inert solvent, such as benzene, toluene or xylene.
  • the sodium salt of camphor is formed by reaction of camphor with a strong non-aqueous 'base, e.g., sodium, sodium hydride, sodium amide or sodium alcoholate.
  • compositions of this invention are produced by blending one or both of the compounds of Formula I with ointment or cream bases, oily or non-oily light-protective ointments or, by mixing with solvents, optionally with the addition of emulsifiers, liquid lightprotective lotions, etc.
  • Suitable additives and solvents are, for example: hydrocarbons, e.g., solid or liquid parafiin, white spirit, ceresin, ozocerite and montan wax; 'vegetable or animal oils, fats and waxes, e.g., olive oil, peanut oil, sesame oil or almond oil, cacao butter, beeswax, fossil wax, or carnauba wax, lanolin and spermaceti; fatty acids and fatty acid esters, e.g., stearic acid, palmitic acid, oleic acid, glycerin monoor distearate, glycerin monooleate, isopropyl myristate, isopropyl stearate and butyl stearate; alcohols, e.g., ethyl, isopropyl, cetyl, stearyl, palmityl and hexyldodecyl alcohol; polyhydric alcohols, e.g.
  • the cosmetic composition of this invention can additionally contain one or more other U.V. absorbents, e.g., the sodium salt of 2-phenyl-benzimidazole-5-sulfonic acid, the sodium salt of 3,4-dimethylphenyl-glyoxylic acid, 4- phenylbenzophenone, the isooctyl ester of 4-phenylbenzophenone 2' carboxylic acid, p-methoxycinnamic acid esters, Z-phenyl 5 methylbenzoxazole and p-dimethylaminobenzoic acid esters.
  • U.V. absorbents e.g., the sodium salt of 2-phenyl-benzimidazole-5-sulfonic acid, the sodium salt of 3,4-dimethylphenyl-glyoxylic acid, 4- phenylbenzophenone, the isooctyl ester of 4-phenylbenzophenone 2' carboxylic acid, p-methoxycinnamic
  • the compounds of Formula I are contained in the agents of this invention in concentrations effective to achieve the desired reduction in transmission of the burning rays.
  • concentrations effective to achieve the desired reduction in transmission of the burning rays The exact concentration is not critical and depends primarily on the particular use.
  • the compositions of this invention contain 0.3-15.0% by weight, preferably 2.012% by weight, of one or both compounds of Formula I.
  • the compositions of this invention additionally contain other U.V. absorbents, the total content of all U.V.-absorbing compounds is usually about 0.3 to 16.5% by weight, preferably 2.0 to 12.0% by weight.
  • concentrations actually used depend on the aimed purpose: high concentrations are desired for compositions with especially high light-protecting factors whereas lower concentrations are suificient for normal cases.
  • the compounds of Formula I can be prepared as described in the literature.
  • 3 cinnamylidene camphor was prepared e.g. as de scribed by H. Rupe and G. Frisell, Ber. dtsch. chem. Ges. 38, 110 (1905).
  • the commercial mixture Lanette N was used, containingf 9t0% cetyl-stearyl alkohole and sodium cetyl-stearyl an a e.
  • a U.V. radiation absorbing cosmetic composition containing a U.V. absorbing effective amount of at least one U.V. absorbing compound of the formula CH-R wherein R is p-tolyl or styryl, in a cosmetically acceptable oil, lotion, cream, ointment or aerosol carrier adapted for application to human skin.
  • composition according to claim 1 containing 3-(4- methylbenzylidene)-D,L-camphor.
  • composition according to claim 1 containing 0.3- 3.5% by weight of the U.V. absorbing agent.
  • composition according to claim 4 containing 0.3- 5.5% by weight of 3-(4-methylbenzylidene)-D,L-camphor.
  • a composition according to claim 5 containing 1.0- 3.0% by weight of 3-(4-methylbenzylidene)-D,L-camphor.
  • composition according to claim 4 containing 0.3- 5.5% by weight of 3-cinnamylidene-D,L-camphor.
  • composition according to claim 7 containing 1.0- 3.0% by weight of 3-cinnamy1idene-D,L-camphor.
  • composition according to claim 4 containing a total of Lil-3.0% by weight of U.V. absorbing agent.
  • a method for the protection of human skin against an overdose of U.V. radiation in the region between 235 and 315 nm. which comprises coating the skin exposed to sunlight with a composition according to claim 1.
  • a method for the protection of human skin against an overdose of U.V. radiation in the region between 285 and 315 nm. which comprises coating the skin exposed to sunlight with a composition according to claim 5.
  • a method for the protection of human skin against an overdose of U.V. radiation in the region between 285 and 315 nm. which comprises coating the skin exposed to sunlight with a composition according to claim 7.
  • a method for the protection of human skin against an overdose of U.V. radiation in the region between 285 and 315 nm. which comprises coating the skin exposed to sunlight with a composition according to claim 9.

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  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Birds (AREA)
  • Dermatology (AREA)
  • Epidemiology (AREA)
  • Emergency Medicine (AREA)
  • Cosmetics (AREA)
US00318998A 1970-10-22 1972-12-27 Light protection agent for cosmetic purposes Expired - Lifetime US3781417A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE2051824A DE2051824C3 (de) 1970-10-22 1970-10-22 Kosmetisches Lichtschutzmittel

Publications (1)

Publication Number Publication Date
US3781417A true US3781417A (en) 1973-12-25

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Family Applications (1)

Application Number Title Priority Date Filing Date
US00318998A Expired - Lifetime US3781417A (en) 1970-10-22 1972-12-27 Light protection agent for cosmetic purposes

Country Status (12)

Country Link
US (1) US3781417A (Direct)
JP (1) JPS5417806B1 (Direct)
AT (2) AT308973B (Direct)
BE (1) BE774076A (Direct)
CH (1) CH563775A5 (Direct)
DE (1) DE2051824C3 (Direct)
ES (1) ES396288A1 (Direct)
FR (1) FR2111757B1 (Direct)
GB (1) GB1310810A (Direct)
IT (1) IT995019B (Direct)
NL (1) NL176224C (Direct)
SE (1) SE393295B (Direct)

Cited By (58)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4165336A (en) * 1973-02-19 1979-08-21 L'oreal (2-Oxo-3-bornylidene methyl)-benzene sulfonates and derivatives thereof
US4290974A (en) * 1978-07-11 1981-09-22 L'oreal Oxybenzylidene-bornanones, their preparation and their use in cosmetics
US4304730A (en) * 1973-02-19 1981-12-08 L'oreal 4-(2-Oxo-3-bornylidene methyl) benzene sulfonic acid and salts thereof
DE3321679A1 (de) * 1982-06-15 1983-12-15 Oreal 3-benzyliden-campher-verbindungen, verfahren zu deren herstellung und verwendung derselben zum schutz gegen uv-strahlung, sowie mittel, die diese enthalten
US4421739A (en) * 1977-03-15 1983-12-20 L'oreal Benzylidene-camphors, processes for their preparation and cosmetic compositions containing them
FR2556592A1 (fr) * 1983-12-14 1985-06-21 Oreal Compositions pharmaceutiques contenant des derives de l'acide campho-methylidene cinnamique
FR2556717A1 (fr) * 1983-12-14 1985-06-21 Oreal Nouveaux derives du 3-benzylidene camphre, leur procede de preparation et leur utilisation en tant qu'agents de protection contre les rayons uv et en tant que medicaments
US4726942A (en) * 1983-02-03 1988-02-23 L'oreal Cosmetic composition for protection against ultraviolet radiation and its use for this purpose
US4731200A (en) * 1983-01-26 1988-03-15 L'oreal Alcoholic or aqueous-alcoholic compositions containing natural essences and benzylidene-camphor derivatives
US4775526A (en) * 1985-12-30 1988-10-04 L'oreal 3-benzylidene benzheterazoles in ultraviolet screening compositions
US4929439A (en) * 1987-02-06 1990-05-29 L'oreal Cosmetic screening composition in the form of an oil-in-water emulsion comprising a UV-A screening compound and a UV-B screening compound and its use for the protection of the skin against ultra-violet radiation
US5047232A (en) * 1986-09-29 1991-09-10 Schering-Plough Healthcare Products, Inc. Non-aqueous waterproof oil-based compositions and method of preparing same
US5783174A (en) * 1992-08-13 1998-07-21 The Procter & Gamble Company Photostable sunscreen compositions
US6059991A (en) * 1997-12-12 2000-05-09 Troy Technology Corporation, Inc. Stabilized composition containing halopropynyl compounds
US6086857A (en) * 1996-03-13 2000-07-11 Basf Aktiengesellschaft Cinnamylidene camphor derivatives and their use as UV-A protecting agents
US20090035240A1 (en) * 2007-07-31 2009-02-05 Maes Daniel H Aqueous Based Cosmetic Compositions Containing Resveratrol Derivatives And An Aqueous Phase Structuring Agent
WO2009017866A1 (en) 2007-07-31 2009-02-05 Elc Management Llc Cosmetic compositions containing resveratrol derivatives
US20090035243A1 (en) * 2007-07-31 2009-02-05 Anna Czarnota Anhydrous Cosmetic Compositions Containing Resveratrol Derivatives
US20090035237A1 (en) * 2007-07-31 2009-02-05 Maes Daniel H Emulsion Cosmetic Compositions Containing Resveratrol Derivatives And Silicone Surfactant
US20090035242A1 (en) * 2007-07-31 2009-02-05 Maes Daniel H Emulsion Cosmetic Compositions Containing Resveratrol Derivatives And Linear Or Branched Silicone
US20090068132A1 (en) * 2007-09-08 2009-03-12 Daniela Bratescu Resveratrol Ferulate Compounds, Compositions Containing The Compounds, And Methods Of Using The Same
US20090092566A1 (en) * 2007-10-09 2009-04-09 Lentini Peter J Self-tanning cosmetic compositions and methods
US20090196942A1 (en) * 2008-02-01 2009-08-06 Goyarts Earl C Topical compositions containing citrus jabara extract
US20090220481A1 (en) * 2009-02-09 2009-09-03 Maes Daniel H Method and compositions for treating skin
US20100015072A1 (en) * 2008-06-30 2010-01-21 Christopher Polla Topical Compositions Comprising Isonicotinamide
US20100028317A1 (en) * 2007-08-13 2010-02-04 Maes Daniel H Skin Repair Compositions Comprising Circadian Gene Activators And A Synergistic Combination Of Sirt1 Gene Activators
US20100080845A1 (en) * 2007-08-13 2010-04-01 Maes Daniel H Cosmetic Methods And Compositions For Repairing Human Skin
US20100203077A1 (en) * 2007-12-19 2010-08-12 Schnittger Steven F Compositions And Methods For Treating Skin With Extract From Trametes
US20100216879A1 (en) * 2007-07-31 2010-08-26 Maes Daniel H Resveratrol Ferulate Compounds And Compositions
US20100233110A1 (en) * 2009-03-13 2010-09-16 Kenneth Cohen Powder Compositions Containing Edible Grains
US20110044919A1 (en) * 2007-08-15 2011-02-24 Giacomoni Paolo U Compositions With Perfluorinated Ingredients
US20110110988A1 (en) * 2009-05-04 2011-05-12 Milanka Susak Topical Compositions Comprising Inorganic Particulates And An Alkoxylated Diphenylacrylate Compound
US20110171149A1 (en) * 2010-01-06 2011-07-14 Yoko Niki Skin Lightening Compositions
US20110171288A1 (en) * 2008-02-20 2011-07-14 Fatemeh Mohammadi Topical compositions and methods for whitening skin
US20110223219A1 (en) * 2010-03-12 2011-09-15 Khanh Ngoc Dao Probiotic Color Cosmetic Compositions And Methods
WO2014107411A1 (en) 2013-01-07 2014-07-10 Elc Management Llc Method and compositions for improving selective catabolysis and viability in cells of keratin surfaces
US8840929B2 (en) 2012-12-11 2014-09-23 Elc Management Llc Cosmetic compositions with near infra-red (NIR) light-emitting material and methods therefor
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US8992897B2 (en) 2010-01-06 2015-03-31 Elc Management Llc Skin lightening compositions
US9072717B2 (en) 2007-09-18 2015-07-07 Elc Management Llc Cosmetic compositions containing alpha glucosidase inhibitors and methods of use
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US9387161B2 (en) 2012-07-25 2016-07-12 Elc Management, Llc Method and compositions for reducing pore size, and moisturizing and/or blurring appearance of defects on keratin surfaces
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DE2728241A1 (de) * 1977-06-23 1979-01-11 Henkel Kgaa Kosmetische lichtschutzmittel fuer den uv-a-bereich
LU84264A1 (fr) * 1982-07-08 1984-03-22 Oreal Nouveaux sulfonamides derives du 3-benzylidene camphre et leur application en tant que filtres u.v.,notamment dans des compositions cosmetiques
LU84608A1 (fr) * 1983-01-26 1984-10-24 Oreal Compositions cosmetiques contenant des essences naturelles et des derives du benzylidene camphre
LU86703A1 (fr) * 1986-12-08 1988-07-14 Oreal Composition cosmetique photostable contenant un filtre uv-a et un filtre uv-b,son utilisation pour la protection de la peau contre les rayons uv et procede de stabilisation du filtre uv-a par le filtre uv-b
LU86997A1 (fr) * 1987-09-21 1989-04-06 Oreal Composition cosmetique filtrante photostable contenant de la bixine associee a un filtre uv liposoluble et son utilisation pour la protection de l'epiderme humain contre les radiations ultraviolettes
DE102004004470A1 (de) 2003-08-01 2005-08-18 Driam Anlagenbau Gmbh Verfahren zum kontinuierlichen Beschichten von Kernen mit einer Dragiervorrichtung und Trennkammern
DE102006019043A1 (de) * 2006-04-25 2007-10-31 Merck Patent Gmbh Antioxidantien
WO2015122992A1 (en) * 2014-02-13 2015-08-20 United Technologies Corporation Nacelle ventilation manifold

Cited By (98)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4304730A (en) * 1973-02-19 1981-12-08 L'oreal 4-(2-Oxo-3-bornylidene methyl) benzene sulfonic acid and salts thereof
US4323549A (en) * 1973-02-19 1982-04-06 L'oreal Anti-solar cosmetic composition
US4327031A (en) * 1973-02-19 1982-04-27 L'oreal Anti-solar cosmetic composition
US4330488A (en) * 1973-02-19 1982-05-18 L'oreal Process of preparing 3-benzylidene-2-oxo-10-bomanesulfonic acid
US4165336A (en) * 1973-02-19 1979-08-21 L'oreal (2-Oxo-3-bornylidene methyl)-benzene sulfonates and derivatives thereof
US4421739A (en) * 1977-03-15 1983-12-20 L'oreal Benzylidene-camphors, processes for their preparation and cosmetic compositions containing them
US4290974A (en) * 1978-07-11 1981-09-22 L'oreal Oxybenzylidene-bornanones, their preparation and their use in cosmetics
US4406880A (en) * 1978-07-11 1983-09-27 L'oreal Oxybenzylidene-bornanones, their preparation and their use in cosmetics
US4585597A (en) * 1982-06-15 1986-04-29 L'oreal 3-benzylidene-camphors, process for their preparation and their use in protection against UV rays
DE3321679A1 (de) * 1982-06-15 1983-12-15 Oreal 3-benzyliden-campher-verbindungen, verfahren zu deren herstellung und verwendung derselben zum schutz gegen uv-strahlung, sowie mittel, die diese enthalten
US4731200A (en) * 1983-01-26 1988-03-15 L'oreal Alcoholic or aqueous-alcoholic compositions containing natural essences and benzylidene-camphor derivatives
US4726942A (en) * 1983-02-03 1988-02-23 L'oreal Cosmetic composition for protection against ultraviolet radiation and its use for this purpose
FR2556717A1 (fr) * 1983-12-14 1985-06-21 Oreal Nouveaux derives du 3-benzylidene camphre, leur procede de preparation et leur utilisation en tant qu'agents de protection contre les rayons uv et en tant que medicaments
US4710584A (en) * 1983-12-14 1987-12-01 L'oreal Derivatives of 3-benzylidene camphor, process for their preparation and their use as protective agents against UV rays and as medicaments
FR2556592A1 (fr) * 1983-12-14 1985-06-21 Oreal Compositions pharmaceutiques contenant des derives de l'acide campho-methylidene cinnamique
DE3445365A1 (de) * 1983-12-14 1985-06-27 L'oreal, Paris Neue 3-benzylidenkampferderivate, verfahren zu deren herstellung und deren verwendung als mittel zum schutz gegen uv-strahlen und als arzneimittel
US4775526A (en) * 1985-12-30 1988-10-04 L'oreal 3-benzylidene benzheterazoles in ultraviolet screening compositions
US5047232A (en) * 1986-09-29 1991-09-10 Schering-Plough Healthcare Products, Inc. Non-aqueous waterproof oil-based compositions and method of preparing same
US4929439A (en) * 1987-02-06 1990-05-29 L'oreal Cosmetic screening composition in the form of an oil-in-water emulsion comprising a UV-A screening compound and a UV-B screening compound and its use for the protection of the skin against ultra-violet radiation
US5783174A (en) * 1992-08-13 1998-07-21 The Procter & Gamble Company Photostable sunscreen compositions
US6086857A (en) * 1996-03-13 2000-07-11 Basf Aktiengesellschaft Cinnamylidene camphor derivatives and their use as UV-A protecting agents
CN1106376C (zh) * 1996-03-13 2003-04-23 Basf公司 肉桂叉樟脑衍生物和它们作为uv－a－光防护剂的应用
US6059991A (en) * 1997-12-12 2000-05-09 Troy Technology Corporation, Inc. Stabilized composition containing halopropynyl compounds
US6353021B1 (en) 1997-12-12 2002-03-05 Troy Technology Corporation, Inc. Stabilized composition containing halopropynyl compounds
US8344024B2 (en) 2007-07-31 2013-01-01 Elc Management Llc Anhydrous cosmetic compositions containing resveratrol derivatives
US8362076B2 (en) 2007-07-31 2013-01-29 Elc Management Llc Ascorbic acid esters of resveratrol and cosmetic compositions
US20090035243A1 (en) * 2007-07-31 2009-02-05 Anna Czarnota Anhydrous Cosmetic Compositions Containing Resveratrol Derivatives
US20090035237A1 (en) * 2007-07-31 2009-02-05 Maes Daniel H Emulsion Cosmetic Compositions Containing Resveratrol Derivatives And Silicone Surfactant
US20090035242A1 (en) * 2007-07-31 2009-02-05 Maes Daniel H Emulsion Cosmetic Compositions Containing Resveratrol Derivatives And Linear Or Branched Silicone
US9162083B2 (en) 2007-07-31 2015-10-20 Elc Management Llc Linoleic and Linolenic acid esters of resveratrol and cosmetic compositions
US9180316B2 (en) 2007-07-31 2015-11-10 Elc Management Llc Butyric acid esters of resveratrol and cosmetic compositions
US9295621B2 (en) 2007-07-31 2016-03-29 Elc Management Llc Emulsion cosmetic compositions containing resveratrol derivatives and silicone surfactant
US8461200B2 (en) 2007-07-31 2013-06-11 Elc Management Llc Salicylic acid esters of resveratrol and cosmetic compositions
WO2009017866A1 (en) 2007-07-31 2009-02-05 Elc Management Llc Cosmetic compositions containing resveratrol derivatives
US20100216879A1 (en) * 2007-07-31 2010-08-26 Maes Daniel H Resveratrol Ferulate Compounds And Compositions
US8080583B2 (en) 2007-07-31 2011-12-20 Elc Management Llc Emulsion cosmetic compositions containing resveratrol derivatives and linear or branched silicone
US20090035240A1 (en) * 2007-07-31 2009-02-05 Maes Daniel H Aqueous Based Cosmetic Compositions Containing Resveratrol Derivatives And An Aqueous Phase Structuring Agent
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AT308974B (de) 1973-07-25
FR2111757B1 (Direct) 1974-10-11
GB1310810A (en) 1973-03-21
CH563775A5 (Direct) 1975-07-15
DE2051824B2 (de) 1975-04-10
NL176224C (nl) 1985-03-18
BE774076A (fr) 1972-04-18
JPS5417806B1 (Direct) 1979-07-03
ES396288A1 (es) 1975-02-16
IT995019B (it) 1975-11-10
DE2051824C3 (de) 1975-11-27
DE2051824A1 (de) 1972-05-04
FR2111757A1 (Direct) 1972-06-09
AT308973B (de) 1973-07-25
NL176224B (nl) 1984-10-16
SE393295B (sv) 1977-05-09
NL7112488A (Direct) 1972-04-25

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