DE29511484U1 - Light protection agents containing p-methoxycinnamate - Google Patents
Light protection agents containing p-methoxycinnamateInfo
- Publication number
- DE29511484U1 DE29511484U1 DE29511484U DE29511484U DE29511484U1 DE 29511484 U1 DE29511484 U1 DE 29511484U1 DE 29511484 U DE29511484 U DE 29511484U DE 29511484 U DE29511484 U DE 29511484U DE 29511484 U1 DE29511484 U1 DE 29511484U1
- Authority
- DE
- Germany
- Prior art keywords
- tocopherol
- light protection
- acetate
- methoxycinnamate
- methoxycinnamic acid
- 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
Links
- AFDXODALSZRGIH-QPJJXVBHSA-N (E)-3-(4-methoxyphenyl)prop-2-enoic acid Chemical compound COC1=CC=C(\C=C\C(O)=O)C=C1 AFDXODALSZRGIH-QPJJXVBHSA-N 0.000 title claims description 7
- 239000011814 protection agent Substances 0.000 title claims description 5
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 claims description 21
- GVJHHUAWPYXKBD-UHFFFAOYSA-N d-alpha-tocopherol Natural products OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 claims description 20
- 229960001295 tocopherol Drugs 0.000 claims description 19
- 239000011732 tocopherol Substances 0.000 claims description 19
- 229930003799 tocopherol Natural products 0.000 claims description 18
- 235000010384 tocopherol Nutrition 0.000 claims description 18
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 6
- YBGZDTIWKVFICR-JLHYYAGUSA-N Octyl 4-methoxycinnamic acid Chemical compound CCCCC(CC)COC(=O)\C=C\C1=CC=C(OC)C=C1 YBGZDTIWKVFICR-JLHYYAGUSA-N 0.000 claims description 6
- 239000003963 antioxidant agent Substances 0.000 claims description 4
- 230000003078 antioxidant effect Effects 0.000 claims description 4
- 230000004224 protection Effects 0.000 claims description 4
- 239000000516 sunscreening agent Substances 0.000 claims description 4
- UBNYRXMKIIGMKK-UHFFFAOYSA-N amiloxate Chemical compound COC1=CC=C(C=CC(=O)OCCC(C)C)C=C1 UBNYRXMKIIGMKK-UHFFFAOYSA-N 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- ZAKOWWREFLAJOT-UHFFFAOYSA-N DL-alpha-tocopherylacetate Chemical compound CC(=O)OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C ZAKOWWREFLAJOT-UHFFFAOYSA-N 0.000 claims 1
- 239000004904 UV filter Substances 0.000 claims 1
- UBNYRXMKIIGMKK-RMKNXTFCSA-N amiloxate Chemical compound COC1=CC=C(\C=C\C(=O)OCCC(C)C)C=C1 UBNYRXMKIIGMKK-RMKNXTFCSA-N 0.000 claims 1
- 230000003711 photoprotective effect Effects 0.000 claims 1
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 9
- 239000004322 Butylated hydroxytoluene Substances 0.000 description 8
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 235000019198 oils Nutrition 0.000 description 4
- 239000000203 mixture Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 2
- 235000006708 antioxidants Nutrition 0.000 description 2
- -1 cinnamic acid ester Chemical class 0.000 description 2
- 239000002537 cosmetic Substances 0.000 description 2
- 239000004611 light stabiliser Substances 0.000 description 2
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
- CNXZMGRWEYQCOQ-UHFFFAOYSA-N 2-methoxy-3-phenylprop-2-enoic acid Chemical class COC(C(O)=O)=CC1=CC=CC=C1 CNXZMGRWEYQCOQ-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 235000019486 Sunflower oil Nutrition 0.000 description 1
- 229930003427 Vitamin E Natural products 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 229940095259 butylated hydroxytoluene Drugs 0.000 description 1
- 229930016911 cinnamic acid Natural products 0.000 description 1
- 235000013985 cinnamic acid Nutrition 0.000 description 1
- 150000001851 cinnamic acid derivatives Chemical class 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 229940079920 digestives acid preparations Drugs 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- WIGCFUFOHFEKBI-UHFFFAOYSA-N gamma-tocopherol Natural products CC(C)CCCC(C)CCCC(C)CCCC1CCC2C(C)C(O)C(C)C(C)C2O1 WIGCFUFOHFEKBI-UHFFFAOYSA-N 0.000 description 1
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
- 229960001679 octinoxate Drugs 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000002600 sunflower oil Substances 0.000 description 1
- 230000000475 sunscreen effect Effects 0.000 description 1
- 239000011709 vitamin E Substances 0.000 description 1
- 235000019165 vitamin E Nutrition 0.000 description 1
- 229940046009 vitamin E Drugs 0.000 description 1
- 239000010497 wheat germ oil Substances 0.000 description 1
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
- 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
- A61K8/67—Vitamins
- A61K8/678—Tocopherol, i.e. vitamin E
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Birds (AREA)
- Emergency Medicine (AREA)
- Dermatology (AREA)
- Cosmetics (AREA)
- Anti-Oxidant Or Stabilizer Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Light Receiving Elements (AREA)
- Investigating Materials By The Use Of Optical Means Adapted For Particular Applications (AREA)
- Photoreceptors In Electrophotography (AREA)
Description
p-Methoxyzimtsäureester enthaltende LichtschutzagentienSunscreen agents containing p-methoxycinnamate
Beschreibung
5Description
5
Die Erfindung betrifft als Schutz gegen UV-Licht wirksame p-Methoxyzimt säureester, die mit Tocopherol bzw. dessen Acetat gegen Oxidation stabilisiert sind.The invention relates to p-methoxycinnamic acid esters which are effective as protection against UV light and which are stabilized against oxidation with tocopherol or its acetate.
p-Methoxyzimtsäureester wie p-Methoxyzimtsäure-2-ethylhexylester oder p-Methoxyzimtsäure-isoamylester sind bekannte Marktprodukte, die als UV-B-Filter in HautSchutzmitteln Verwendung finden. Diese Lichtschutzagentien sind üblicherweise mit BHT (butyliertes Hydroxytoluol, 2,6-Di-t-butyl-p-kresol) in Mengen bis zu 1 Gew.-% stabilisiert.p-Methoxycinnamic acid esters such as p-methoxycinnamic acid 2-ethylhexyl ester or p-methoxycinnamic acid isoamyl ester are well-known market products that are used as UV-B filters in skin protection products. These light protection agents are usually stabilized with BHT (butylated hydroxytoluene, 2,6-di-t-butyl-p-cresol) in amounts of up to 1% by weight.
Obgleich BHT sehr gute stabilisierende Eigenschaften hat, ist es erwünscht, in Präparationen, die mit dem menschlichen Körper in Kontakt kommen, BHT durch natürliche Antioxidantien zu ersetzen.Although BHT has very good stabilizing properties, it is desirable to replace BHT with natural antioxidants in preparations that come into contact with the human body.
Als in der Natur in verschiedenen Ölen vorkommendes Antioxidans ist Tocopherol wohlbekannt und wird bereits auf vielen Gebieten der Nahrungsmittel- und kosmetischen Industrie verwendet, wobei sowohl die Vitamin-E-Wirkung als auch die Antioxidans-Wirkung nebeneinander zur Geltung kommen. Im Vergleich zu BHT ist Tocopherol jedoch teurer und galt im allgemeinen als weniger wirksam bezogen auf die zu verwendende Menge.As an antioxidant that occurs naturally in various oils, tocopherol is well known and is already used in many areas of the food and cosmetic industries, where both the vitamin E and antioxidant effects come into play alongside one another. However, compared to BHT, tocopherol is more expensive and is generally considered less effective in relation to the amount used.
Es wurde nun überraschenderweise gefunden, daß als Lichtschutzmittel wirkende p-Methoxyzimtsäureester statt mit BHT verbessert mit Tocopherol bzw. dessen Estern in Mengen von 0,01 bis 1 Gew.-% stabilisiert werden können, wobei bei Tocopherolzusatz die Lichtschutzagentien besonders bei längerer Lagerung besser stabilisiert werden und bei leicht erhöhter Tempratur keine Geruchsveränderungen aufweisen, während die herkömmlichen BHT-stabilisierten Agentien einen unerwünschten apfelartigen Geruch entwickeln.It has now surprisingly been found that p-methoxycinnamic acid esters acting as light stabilizers can be better stabilized with tocopherol or its esters in amounts of 0.01 to 1% by weight instead of BHT, whereby the light stabilizers are better stabilized with the addition of tocopherol, particularly during longer storage, and do not show any changes in odor at slightly higher temperatures, whereas the conventional BHT-stabilized agents develop an undesirable apple-like odor.
Gegenstand der Erfindung sind somit neue Stoffmischungen, bestehend ausschließlich aus (a) p-Methoxyzimtsäureestern und (b) untergeordneten Mengen Tocopherol bzw. dessen Acetat.The invention therefore relates to new mixtures of substances consisting exclusively of (a) p-methoxycinnamic acid esters and (b) minor amounts of tocopherol or its acetate.
Als Methoxyzimtsäureester kommen bevorzugt p-Methoxyzimtsäure-2-ethylhexylester oder -isoamylester in Betracht. Tocopherol ist vor allem cc-Tocopherol und dessen Acetat. Es kann entweder aus natürlichen Quellen, wie z.B. aus Sojadämpferöl, oder bevorzugt synthetisch hergestellt sein.The preferred methoxycinnamic acid esters are p-methoxycinnamic acid 2-ethylhexyl ester or -isoamyl ester. Tocopherol is mainly cc-tocopherol and its acetate. It can either be produced from natural sources, such as soy steamer oil, or preferably synthetically.
BASF Aktiengesellschaft·BASF Aktiengesellschaft·
0050/460190050/46019
Die Zusatzmengen des Tocopherols betragen in der Regel 0,01, bevorzugt 0,1 bis 1 Gew.-%, doch sind au größere Mengen möglich, die aber keine weitere Verbesserung der Stabilität bewirken. Demgemäß bestehen die neuen Stoffmischungen aus 99 bis 99,99, bevorzugt 99,9 Gew.-% Methoxyzimtsäureester und 0,01, bevorzugt 0,1 bis 1 Gew.-% Tocopherol.The amount of tocopherol added is generally 0.01, preferably 0.1 to 1% by weight, but larger amounts are also possible, although these do not result in any further improvement in stability. Accordingly, the new mixtures consist of 99 to 99.99, preferably 99.9% by weight of methoxycinnamate and 0.01, preferably 0.1 to 1% by weight of tocopherol.
Die Einmischung des Tocopherols erfolgt durch direktes Vermischen bzw. Einrühren des Tocopherols oder durch Einrühren einer konzentrierteren Lösung z.B. 10 % Vorlösung in dem entsprechenden Zimtsäureester. The tocopherol is mixed in by directly mixing or stirring in the tocopherol or by stirring in a more concentrated solution, e.g. 10% pre-solution in the corresponding cinnamic acid ester.
Für die Weiterverarbeitung der stabilisierten Zimt säureester in der kosmetischen Industrie zu Lichtschutzpräparationen stört der Tocopherolgehalt, insbesondere ein über die Wirksamkeitserfordernis erhöhter Gehalt an Tocopherol, nicht, da diese Präparationen in zunehmendem Maße natürliche Öle, wie Sonnenblumenöle, Weizenkeimöl oder Maiskaimöl enthalten, die ohnehin einen {geringen Gehalt an Tocopherol aufweisen.For the further processing of the stabilized cinnamic acid esters in the cosmetic industry to produce sunscreen preparations, the tocopherol content, especially a tocopherol content that exceeds the effectiveness requirement, is not a problem, since these preparations increasingly contain natural oils, such as sunflower oil, wheat germ oil or corn caim oil, which already have a low tocopherol content.
Die neuen stabilisierten p-Methoxy&zgr;imtSäurezubereitungen zeichnen sich durch eine ausgezeichnete Lagerstabilität aus.The new stabilized p-methoxyζimt acid preparations are characterized by excellent storage stability.
p-Methoxyzimtsäure-2-ethylhexylester wird mit 0,1 Gew.-%, bezogen auf die Gesamtmischung an a-Tocopherol versetzt und durch Rühren gleichmäßig verteilt. Solcherart stabilisierte Proben werden bei 6°C, bei Raumtemperatur und bei 45°C in Polyethylenflaschen unter Luftabschluß gelagert. Die spezifische Absorption einer 1 %igen Lösung in Ethanol, gemessen in einer Schichtdicke von einem cm, der sogenannten E -j- -Wert in Ethanol, beträgt nach neunmonatiger Lagerung bei 6°C 869, bei Raumtemperatur 866 und bei 450C 858. Parallel unter gleichen Bedingungen gelagert Proben, die mit entsprechenden Mengen BHT stabilisiert waren, wiesen mit E !j· = 854 bei 6°C-Lagerung, 864 bei Raumtemperatur und 856 bei 45°C etwas geringere Werte für die spezifische Absorption auf, die ein empfindliches Maß für den Wirkstoffgehalt darstellt. In Bezug auf die Farbzahl unterschieden sich die verschieden stabilisierten Proben nicht.0.1% by weight of a-tocopherol, based on the total mixture, is added to p-methoxycinnamic acid-2-ethylhexyl ester and evenly distributed by stirring. Samples stabilized in this way are stored in polyethylene bottles at 6°C, at room temperature and at 45°C under exclusion of air. The specific absorption of a 1% solution in ethanol, measured in a layer thickness of one cm, the so-called E -j- value in ethanol, is 869 after nine months of storage at 6°C, 866 at room temperature and 858 at 45 0 C. Samples stored in parallel under the same conditions which were stabilized with corresponding amounts of BHT showed slightly lower values for the specific absorption, which is a sensitive measure of the active ingredient content, with E !j· = 854 when stored at 6°C, 864 at room temperature and 856 at 45°C. With regard to the color number, the differently stabilized samples did not differ.
Ferner wiesen die mit Tocopherol stabilisierten Proben keine Geruchsveränderungen auf, während die mit BHT stabilisierte und bei 450C gelagerte Proben einen unerwünschten apfelartigen Geruch entwickelte. Furthermore, the samples stabilized with tocopherol showed no odor changes, while the samples stabilized with BHT and stored at 45 ° C developed an undesirable apple-like odor.
Claims (6)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE29511484U DE29511484U1 (en) | 1995-07-15 | 1995-07-15 | Light protection agents containing p-methoxycinnamate |
| JP8179425A JPH09104856A (en) | 1995-07-15 | 1996-07-09 | Light-intercepting agent stabilized against oxidation |
| DE29611889U DE29611889U1 (en) | 1995-07-15 | 1996-07-09 | Light protection agents containing p-methoxycinnamate |
| IT96MI000497U ITMI960497U3 (en) | 1995-07-15 | 1996-07-12 | LIGHT PROTECTIVE AGENTS CONTAINING P-METHOXICINNAMIC ACID ESTERS |
| IT96MI001443A IT1283144B1 (en) | 1995-07-15 | 1996-07-12 | PHOTOPROTECTOR AGENTS CONTAINING FOREIGN P-METHOXYNYNAMIC ACID |
| ES09601577A ES2120892B1 (en) | 1995-07-15 | 1996-07-15 | PROTECTIVE AGENTS AGAINST LIGHT CONTAINING ESTERS OF P-METOXYCINAMIC ACID. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE29511484U DE29511484U1 (en) | 1995-07-15 | 1995-07-15 | Light protection agents containing p-methoxycinnamate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE29511484U1 true DE29511484U1 (en) | 1995-10-05 |
Family
ID=8010589
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE29511484U Expired - Lifetime DE29511484U1 (en) | 1995-07-15 | 1995-07-15 | Light protection agents containing p-methoxycinnamate |
| DE29611889U Expired - Lifetime DE29611889U1 (en) | 1995-07-15 | 1996-07-09 | Light protection agents containing p-methoxycinnamate |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE29611889U Expired - Lifetime DE29611889U1 (en) | 1995-07-15 | 1996-07-09 | Light protection agents containing p-methoxycinnamate |
Country Status (4)
| Country | Link |
|---|---|
| JP (1) | JPH09104856A (en) |
| DE (2) | DE29511484U1 (en) |
| ES (1) | ES2120892B1 (en) |
| IT (2) | IT1283144B1 (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4091746B2 (en) | 2001-02-06 | 2008-05-28 | 日清オイリオグループ株式会社 | Use for improving the stability of UV-absorbing substances, UV absorbers and cosmetics |
| US6869598B2 (en) * | 2002-03-22 | 2005-03-22 | Unilever Home & Personal Care Usa Division Of Conopco, Inc. | Stabilization of sunscreens in cosmetic compositions |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1022749A (en) * | 1963-12-21 | 1966-03-16 | Fujisawa Pharmaceutical Co | Tocopheryl 3,4-disubstituted cinnamates and their preparation |
| JPH0625053B2 (en) * | 1986-05-15 | 1994-04-06 | 株式会社資生堂 | External skin preparation |
| US4833259A (en) * | 1986-09-15 | 1989-05-23 | Hoffmann-La Roche Inc. | Light screening agents |
| US4847072A (en) * | 1987-10-22 | 1989-07-11 | The Procter & Gamble Company | Photoprotection compositions comprising tocopherol sorbate |
-
1995
- 1995-07-15 DE DE29511484U patent/DE29511484U1/en not_active Expired - Lifetime
-
1996
- 1996-07-09 JP JP8179425A patent/JPH09104856A/en active Pending
- 1996-07-09 DE DE29611889U patent/DE29611889U1/en not_active Expired - Lifetime
- 1996-07-12 IT IT96MI001443A patent/IT1283144B1/en active IP Right Grant
- 1996-07-12 IT IT96MI000497U patent/ITMI960497U3/en unknown
- 1996-07-15 ES ES09601577A patent/ES2120892B1/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| ITMI960497U3 (en) | 1998-01-12 |
| DE29611889U1 (en) | 1996-09-12 |
| ES2120892A1 (en) | 1998-11-01 |
| ITMI961443A1 (en) | 1998-01-12 |
| JPH09104856A (en) | 1997-04-22 |
| ITMI961443A0 (en) | 1996-07-12 |
| IT1283144B1 (en) | 1998-04-07 |
| ITMI961443A3 (en) | 1998-01-12 |
| ITMI960497V0 (en) | 1996-07-12 |
| ES2120892B1 (en) | 1999-07-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| R207 | Utility model specification |
Effective date: 19951116 |
|
| R156 | Lapse of ip right after 3 years |
Effective date: 19980829 |