US3781417A - Light protection agent for cosmetic purposes - Google Patents

Light protection agent for cosmetic purposes Download PDF

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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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camphor
radiation
oil
methylbenzylidene
sunlight
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US00318998A
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R Welters
H Russmann
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Merck Patent GmbH
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Merck Patent GmbH
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    • 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.

Abstract

TOPICAL COSMETIC COMPOSITIONS CONTAINING AS AN ULTRAVIOLET ABSORBENT COMPRISING A COMPOUND OF THE FORMULA

2-(O=),3-(R-CH=),1,7,7-TRI(CH3-)NORBORNANE

WHEREIN R IS P-TOLYL OR STYRYL.

Description

United States Patent Oifice 3,781,417 Patented Dec. 25, 1973 US. Cl. 424-59 13 Claims ABSTRACT OF THE DISCLOSURE Topical cosmetic compositions containing as an ultraviolet absorbent comprising a compound of the formula wherein R is p-tolyl or styryl.
This application is a continuation-in-part of our application Ser. No. 190,630, filed Oct. 19, 1971, now abandoned.
BACKGROUND OF THE INVENTION This invention relates to cosmetic compositions containing a UV absorbent.
As is known, light rays of a wavelength range of 285- 315 nm. cause sunburn and erythemas inv normally fairskinned humans, whereas radiation of the wavelength range of 3l0400 nm. is responsible for the desired tanning of the skin. 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.
On the other hand, there are persons who for health reasons must be protected also from radiation of a longer wavelength than 315 nm., to ensure that the sunlight is absorbed in the wavelength range of 285-360 nm. This is achieved by so-called broad-band filters.
The requirements of a good light protection agent, which are not always simultaneously fulfilled by the classes of compounds known as cosmetic light protection agents which are commercially available, are as follows:
(a) A high absorption capacity between 285 nm. and 315 nm., in order to provide adequate protection against sunburn at low concentrations;
(b) A low absorption capacity in the light range which promotes direct pigmentation, in order to achieve the desired tanning effect;
(c) Solubility in the solvents customary in cosmetics;
(d) Adequate stability of the final product under the conditions of use, e.g., sunlight, elevated temperature and perspiration; and
(e) Good compatibility with the skin.
It has now been found that all of these conditions are met in an excellent manner by 3-(4-methylbenzylidene) D,L-camphor (I; R=p-tolyl). Thus, for example, the solubility of this compound in paraffin oil is almost three times as high as that of 3-benzylidene camphor, the use of which as a stabilizer and protective agent of cosmetic preparations against light radiation is known from German published unexamined application DOS 1,913,489.
It has also been discovered that 3-cinnamylidene-D,L- camphor is characterized by an excellent broad-band filter effect.
SUMMARY OF THE INVENTION In a composition aspect, 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.
This invention also relates to such compositions whic additionally contain one or more other U.V. absorbents.
In a method of use aspect, 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.
From the table set forth below, the superior light absorption behavior of the 3-(4-methyl'benzylidene)-D,L- camphor of the compositions of this invention can be seen when compared to two commercial products of proven capabilities, viz., p-methoxycinnamic acid 2.-eth oxyethyl ester (=A), and the isopropyl ester of p-methoxycinnamic acid (=B). The transmittance values of the U.V.-absorbers were all measured at 0.002% strength in isopropanol solutions.
Transmittance (in percent) Whereas 3-(4-methylbenzylidene) D,L camphor exhibits at 297 nm., i.e., in the center of the zone of erythema-producing radiation, only half the transmittance of the products A and B, the active compound of the compositions of this invention exhibits at 330 nm., i.e., the center of the tanning radiation, a transmittance which is 1.5-2.5 times larger than the reference compounds.
The 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%.
The 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.
These 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.
The cosmetic 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., glycol, glycerin and sorbitol, which serve as moisturizing agents; emulsifiers for oil in water and water in oil emulsions, e.g., the commercially available ionic or nonionic, cationic or anionic or ampholytic emulsifiers; and thickeners, e.g., methyl, ethyl or carboxymethyl cellulose, polyacrylic acid, tragacanth, agar and gelatin. It is, of course, possible to also add, if required or desired, further additives such as perfumes, preservatives or physiologically acceptable coloring agents.
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.
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. The exact concentration is not critical and depends primarily on the particular use. In general, 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. When 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. The 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 numerical values in the formulation examples set forth below are parts by weight.
Without further elaboration, it is believed that one skilled in the art can, using the preceding description, utilize the present invention to its fullest extent. The following preferred specific embodiments are, therefore, to be construed as merely illustrative, and not limitative of the remainder of the disclosure in any Way whatsoever.
The compounds of Formula I can be prepared as described in the literature.
3-(4-methylbenzylidene)-D,L-camphor (I; R=p-tolyl) was prepared e.g. following the method of A. Haller and E. Bauer, Compt. rend. 148, 1493 (1909).
3 cinnamylidene camphor was prepared e.g. as de scribed by H. Rupe and G. Frisell, Ber. dtsch. chem. Ges. 38, 110 (1905).
Example A Suntan oil:
3-(4-methylbenzylidene)-D,L-camphor 2 Liquid parafiin 48 2-octyl dodecanol 50 Example B Sunlight protection oil:
3-(4-methylbenzylidene)-D,L-camphor 2 Liquid parafiin 50 Isopropyl myristate 48 Example C Suntan lotion:
3-(4-methylbenzylidene)-D,L-carnphor 1.5 Liquid paraffin 10.0 Polyol monostearate ethoxylate 10.0 Isopropyl myristate 10.0 Sorbitol solution 70% 5.0 Sodium lauryl ether sulfate 0.5 Water 63.0
Example D Sunlight protection cream:
3-(4-methylbenzylidene)-D,L-camphor 2.5 Lanolin 67.0 Olive oil 10.0 Water 20.5
Example E Aerosol:
Mixture according to Example A or B 40 Mixture of trichlorofiuoromethane and dichlorodifiuoromethane (70:30) (propellant gas) 60 Example F Sunlight protection cream:
3-cinnamylidene-D,L-camphor 2 Triethanolamine salt of 2-phenyl-benzirnidazole 5-sulfonic acid, 50% 3 Cream base (system oil/water or water/oil) Example G preparation is indicated particularly in the high mountain region.
Example H Sunlight protection oil:
3-(4-methylbenzylidene)-D,L-camphor 10 Isopropyl myristate 15 Liquid paraflin 75 Example I Sunlight protection cream:
The commercial mixture Lanette N was used, containingf 9t0% cetyl-stearyl alkohole and sodium cetyl-stearyl an a e.
Example I Sunlight protection cream:
3-(4-methylbenzylidene)-D,L-camphor 1O Glycerinmonostearate 2 Spermaceti 3 Eucerin anhydricum 40 4-hydroxybenzoic acid methylester 0.12 Water 44.88
Example K Sunlight protection oil:
3-(4-methylbenzylidene)-D,L-camphor 7.5 Isopropyl myristate Liquid parafiin 77.5
Example L Sunlight protection cream:
3-cinnamylidene-D,L-camphor 6 Glycerinmonostearate 2 Spermaceti 3 Eucerin anhydricum 40 4-hydroxybenzoic acid methylester 0.12 Water 48.88
The preceding examples can be repeated with similar success by substituting the generically and specifically described reactants and/ or operating conditions of this invention for those used in the preceding examples.
From the foregoing description, one skilled in the art can easily ascertain the essential characteristics of this invention, and without departing from the spirit and scope thereof, can make various changes and modifications of the invention to adapt it to various usages and conditions.
What is claimed is:
1. 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.
2. A composition according to claim 1 containing 3-(4- methylbenzylidene)-D,L-camphor.
3. A composition according to claim 1 containing 3- cinnamylidene-D,L-camphor.
4. A composition according to claim 1 containing 0.3- 3.5% by weight of the U.V. absorbing agent.
5. A composition according to claim 4 containing 0.3- 5.5% by weight of 3-(4-methylbenzylidene)-D,L-camphor.
6. A composition according to claim 5 containing 1.0- 3.0% by weight of 3-(4-methylbenzylidene)-D,L-camphor.
7. A composition according to claim 4 containing 0.3- 5.5% by weight of 3-cinnamylidene-D,L-camphor.
8. A composition according to claim 7 containing 1.0- 3.0% by weight of 3-cinnamy1idene-D,L-camphor.
9. A composition according to claim 4 containing a total of Lil-3.0% by weight of U.V. absorbing agent.
10. 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.
11. 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.
12. 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.
13. 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.
References Cited De Navarre: The Chemistry & Manufacture of Cosmetics (1941), PP- 591-593.
SAM ROSEN, Primary Examiner US. Cl. X.R. 42.4332
- TED STATES PATENT oTTTQT QERTIHCATE @F CQRREUHGN Patent No. 3, 781 417 Dated December 25 19773 lnventofls) Reiner Welters et a1.
It is certified that error appears in the above-identified patent and that said Letters Patent are hereby corrected as shown below:
IN THE CLAIMS: I
CLAIM 4, COLUMN- 6: "3.5%" should read 5.,5o
CLAIM 10, comm e; "235" should read 285 Signed and sealed this 9th day of April 197'4,
(SEAL) Attest:
EDL'JARD PLFLETCHER,JR 0., MARSHALL DANN Attesting Officer Commissioner of Patents USCOMM-DC 60376-P69 w u.s, covsnuuzm PRINTING OFFICE: nu 0-366-334.
: ORM PO-1050 (10-69)
US00318998A 1970-10-22 1972-12-27 Light protection agent for cosmetic purposes Expired - Lifetime US3781417A (en)

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DE (1) DE2051824C3 (en)
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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 (en) * 1982-06-15 1983-12-15 Oreal 3-BENZYLIDE-CAMPHER COMPOUNDS, METHOD FOR THE PRODUCTION THEREOF AND THE USE THEREOF FOR PROTECTION AGAINST UV RADIATION, AND MEANS THAT CONTAIN THEM
US4421739A (en) * 1977-03-15 1983-12-20 L'oreal Benzylidene-camphors, processes for their preparation and cosmetic compositions containing them
FR2556717A1 (en) * 1983-12-14 1985-06-21 Oreal NOVEL 3-BENZYLIDENE CAMPHRE DERIVATIVES, PROCESS FOR THEIR PREPARATION AND THEIR USE AS PROTECTIVE AGENTS AGAINST UV RAYS AND AS MEDICAMENTS
FR2556592A1 (en) * 1983-12-14 1985-06-21 Oreal Pharmaceutical compositions containing camphormethylidenecinnamic acid derivatives
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
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
WO2009017866A1 (en) 2007-07-31 2009-02-05 Elc Management Llc Cosmetic compositions containing resveratrol derivatives
US20090035240A1 (en) * 2007-07-31 2009-02-05 Maes Daniel H Aqueous Based Cosmetic Compositions Containing Resveratrol Derivatives And An Aqueous Phase Structuring Agent
US20090035243A1 (en) * 2007-07-31 2009-02-05 Anna Czarnota Anhydrous Cosmetic Compositions Containing Resveratrol Derivatives
US20090068132A1 (en) * 2007-09-08 2009-03-12 Daniela Bratescu Resveratrol Ferulate Compounds, Compositions Containing The Compounds, And Methods Of Using The Same
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SE393295B (en) 1977-05-09
NL176224C (en) 1985-03-18
BE774076A (en) 1972-04-18
JPS5417806B1 (en) 1979-07-03
DE2051824C3 (en) 1975-11-27
DE2051824B2 (en) 1975-04-10
FR2111757A1 (en) 1972-06-09
NL7112488A (en) 1972-04-25
ES396288A1 (en) 1975-02-16
NL176224B (en) 1984-10-16
AT308973B (en) 1973-07-25
CH563775A5 (en) 1975-07-15
GB1310810A (en) 1973-03-21
DE2051824A1 (en) 1972-05-04
AT308974B (en) 1973-07-25
IT995019B (en) 1975-11-10
FR2111757B1 (en) 1974-10-11

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