DE19638534A1 - Use of tocopheryl ferulate as skin bleaching agent - Google Patents
Use of tocopheryl ferulate as skin bleaching agentInfo
- Publication number
- DE19638534A1 DE19638534A1 DE1996138534 DE19638534A DE19638534A1 DE 19638534 A1 DE19638534 A1 DE 19638534A1 DE 1996138534 DE1996138534 DE 1996138534 DE 19638534 A DE19638534 A DE 19638534A DE 19638534 A1 DE19638534 A1 DE 19638534A1
- Authority
- DE
- Germany
- Prior art keywords
- acid
- cosmetic
- oil
- derivatives
- skin
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
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- 125000001117 oleyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- BARWIPMJPCRCTP-CLFAGFIQSA-N oleyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCCOC(=O)CCCCCCC\C=C/CCCCCCCC BARWIPMJPCRCTP-CLFAGFIQSA-N 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- DXGLGDHPHMLXJC-UHFFFAOYSA-N oxybenzone Chemical compound OC1=CC(OC)=CC=C1C(=O)C1=CC=CC=C1 DXGLGDHPHMLXJC-UHFFFAOYSA-N 0.000 description 1
- LXTZRIBXKVRLOA-UHFFFAOYSA-N padimate a Chemical compound CCCCCOC(=O)C1=CC=C(N(C)C)C=C1 LXTZRIBXKVRLOA-UHFFFAOYSA-N 0.000 description 1
- 239000003346 palm kernel oil Substances 0.000 description 1
- 235000019865 palm kernel oil Nutrition 0.000 description 1
- 239000002540 palm oil Substances 0.000 description 1
- 229940098695 palmitic acid Drugs 0.000 description 1
- 125000001312 palmitoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000000467 phytic acid Substances 0.000 description 1
- 235000002949 phytic acid Nutrition 0.000 description 1
- 229940068041 phytic acid Drugs 0.000 description 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
- 229920003216 poly(methylphenylsiloxane) Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 150000008442 polyphenolic compounds Chemical class 0.000 description 1
- 235000013824 polyphenols Nutrition 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- PZQSQRCNMZGWFT-QXMHVHEDSA-N propan-2-yl (z)-octadec-9-enoate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC(C)C PZQSQRCNMZGWFT-QXMHVHEDSA-N 0.000 description 1
- ZPWFUIUNWDIYCJ-UHFFFAOYSA-N propan-2-yl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC(C)C ZPWFUIUNWDIYCJ-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229960002662 propylthiouracil Drugs 0.000 description 1
- 235000018102 proteins Nutrition 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 230000002797 proteolythic effect Effects 0.000 description 1
- 238000004080 punching Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- IKGXIBQEEMLURG-BKUODXTLSA-N rutin Chemical compound O[C@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@@H]1OC[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](OC=2C(C3=C(O)C=C(O)C=C3OC=2C=2C=C(O)C(O)=CC=2)=O)O1 IKGXIBQEEMLURG-BKUODXTLSA-N 0.000 description 1
- 229960004555 rutoside Drugs 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 230000037390 scarring Effects 0.000 description 1
- 239000011669 selenium Substances 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 229960002718 selenomethionine Drugs 0.000 description 1
- 229940057910 shea butter Drugs 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 230000009759 skin aging Effects 0.000 description 1
- 235000002639 sodium chloride Nutrition 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- 239000001540 sodium lactate Substances 0.000 description 1
- 229940005581 sodium lactate Drugs 0.000 description 1
- 235000011088 sodium lactate Nutrition 0.000 description 1
- CRPCXAMJWCDHFM-UHFFFAOYSA-M sodium;5-oxopyrrolidine-2-carboxylate Chemical compound [Na+].[O-]C(=O)C1CCC(=O)N1 CRPCXAMJWCDHFM-UHFFFAOYSA-M 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 229940032094 squalane Drugs 0.000 description 1
- 229940031439 squalene Drugs 0.000 description 1
- TUHBEKDERLKLEC-UHFFFAOYSA-N squalene Natural products CC(=CCCC(=CCCC(=CCCC=C(/C)CCC=C(/C)CC=C(C)C)C)C)C TUHBEKDERLKLEC-UHFFFAOYSA-N 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- ARCJQKUWGAZPFX-UHFFFAOYSA-N stilbene oxide Chemical compound O1C(C=2C=CC=CC=2)C1C1=CC=CC=C1 ARCJQKUWGAZPFX-UHFFFAOYSA-N 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 150000001629 stilbenes Chemical class 0.000 description 1
- 210000000438 stratum basale Anatomy 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 150000003458 sulfonic acid derivatives Chemical class 0.000 description 1
- 125000005555 sulfoximide group Chemical group 0.000 description 1
- CXVGEDCSTKKODG-UHFFFAOYSA-N sulisobenzone Chemical compound C1=C(S(O)(=O)=O)C(OC)=CC(O)=C1C(=O)C1=CC=CC=C1 CXVGEDCSTKKODG-UHFFFAOYSA-N 0.000 description 1
- 239000002600 sunflower oil Substances 0.000 description 1
- UEUXEKPTXMALOB-UHFFFAOYSA-J tetrasodium;2-[2-[bis(carboxylatomethyl)amino]ethyl-(carboxylatomethyl)amino]acetate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]C(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O UEUXEKPTXMALOB-UHFFFAOYSA-J 0.000 description 1
- REZOIPSCCRVWNN-UHFFFAOYSA-N tetratriacontan-17-ol Chemical compound CCCCCCCCCCCCCCCCCC(O)CCCCCCCCCCCCCCCC REZOIPSCCRVWNN-UHFFFAOYSA-N 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- 229960002663 thioctic acid Drugs 0.000 description 1
- 235000019303 thiodipropionic acid Nutrition 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 229940094937 thioredoxin Drugs 0.000 description 1
- 108060008226 thioredoxin Proteins 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 229940042585 tocopherol acetate Drugs 0.000 description 1
- 230000002110 toxicologic effect Effects 0.000 description 1
- 231100000027 toxicology Toxicity 0.000 description 1
- QURCVMIEKCOAJU-UHFFFAOYSA-N trans-isoferulic acid Natural products COC1=CC=C(C=CC(O)=O)C=C1O QURCVMIEKCOAJU-UHFFFAOYSA-N 0.000 description 1
- ZCIHMQAPACOQHT-ZGMPDRQDSA-N trans-isorenieratene Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/c1c(C)ccc(C)c1C)C=CC=C(/C)C=Cc2c(C)ccc(C)c2C ZCIHMQAPACOQHT-ZGMPDRQDSA-N 0.000 description 1
- LOIYMIARKYCTBW-OWOJBTEDSA-N trans-urocanic acid Chemical compound OC(=O)\C=C\C1=CNC=N1 LOIYMIARKYCTBW-OWOJBTEDSA-N 0.000 description 1
- LOIYMIARKYCTBW-UHFFFAOYSA-N trans-urocanic acid Natural products OC(=O)C=CC1=CNC=N1 LOIYMIARKYCTBW-UHFFFAOYSA-N 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-O triethanolammonium Chemical class OCC[NH+](CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-O 0.000 description 1
- 229940040064 ubiquinol Drugs 0.000 description 1
- QNTNKSLOFHEFPK-UPTCCGCDSA-N ubiquinol-10 Chemical compound COC1=C(O)C(C)=C(C\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CCC=C(C)C)C(O)=C1OC QNTNKSLOFHEFPK-UPTCCGCDSA-N 0.000 description 1
- 229940035936 ubiquinone Drugs 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 229940116269 uric acid Drugs 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- NCYCYZXNIZJOKI-UHFFFAOYSA-N vitamin A aldehyde Natural products O=CC=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C NCYCYZXNIZJOKI-UHFFFAOYSA-N 0.000 description 1
- 235000019154 vitamin C Nutrition 0.000 description 1
- 239000011718 vitamin C Substances 0.000 description 1
- 150000003722 vitamin derivatives Chemical class 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- 230000029663 wound healing Effects 0.000 description 1
- 229940120347 zinc preparations Drugs 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
- OENHQHLEOONYIE-JLTXGRSLSA-N β-Carotene Chemical compound CC=1CCCC(C)(C)C=1\C=C\C(\C)=C\C=C\C(\C)=C\C=C\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C OENHQHLEOONYIE-JLTXGRSLSA-N 0.000 description 1
- 235000007680 β-tocopherol Nutrition 0.000 description 1
- 239000011590 β-tocopherol Substances 0.000 description 1
- FGYKUFVNYVMTAM-WAZJVIJMSA-N β-tocotrienol Chemical compound OC1=CC(C)=C2O[C@@](CC/C=C(C)/CC/C=C(C)/CCC=C(C)C)(C)CCC2=C1C FGYKUFVNYVMTAM-WAZJVIJMSA-N 0.000 description 1
- 239000002478 γ-tocopherol Substances 0.000 description 1
- QUEDXNHFTDJVIY-DQCZWYHMSA-N γ-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1 QUEDXNHFTDJVIY-DQCZWYHMSA-N 0.000 description 1
- 239000002446 δ-tocopherol 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
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/4973—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom
- A61K8/498—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom having 6-membered rings or their condensed derivatives, e.g. coumarin
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
- A61K31/352—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom condensed with carbocyclic rings, e.g. methantheline
- A61K31/353—3,4-Dihydrobenzopyrans, e.g. chroman, catechin
- A61K31/355—Tocopherols, e.g. vitamin E
-
- 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)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Epidemiology (AREA)
- Birds (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Dermatology (AREA)
- Cosmetics (AREA)
Abstract
Description
Die vorliegende Erfindung betrifft die Verwendung an sich bekannter Wirkstoffe, zur kosmetischen und topischen dermatologischen zur Hautaufhellung oder zur Verhinderung der Hautbräunung, insbesondere der durch UV-Strahlung her vorgerufenen Hautbräunung.The present invention relates to the use of active substances known per se, for cosmetic and topical dermatological skin lightening or for Preventing the tanning of the skin, in particular that caused by UV radiation called skin tanning.
In einer bevorzugten Ausführungsform betrifft die vorliegende Erfindung kosmeti sche und dermatologische Zubereitungen zur Prophylaxe und Behandlung kosme tischer oder dermatologischer Hautveränderungen wie z. B. der unerwünschten Pigmentierung, beispielsweise lokale Hyper- und Fehlpigmentierungen (beispiels weise Leberflecken, Sommersprossen), aber auch zur rein kosmetischen Aufhel lung größerer, dem individuellen Hauttyp an sich durchaus angemessen pigmen tierter Hautflächen.In a preferred embodiment, the present invention relates cosmeti cosmetic and dermatological preparations for prophylaxis and treatment dermal or dermatological lesions such. B. the undesirable Pigmentation, for example local hyper- and false pigmentation (e.g. as liver spots, freckles), but also for purely cosmetic Aufhel Larger, the individual skin type in itself quite appropriate pigmen derated skin areas.
Für die Pigmentierung der Haut verantwortlich sind die Melanozyten, welche in der untersten Schicht der Epidermis, dem Stratum basale, neben den Basalzellen als - je nach Hauttyp entweder vereinzelt oder aber mehr oder weniger gehäuft auftre tende pigmentbildende Zellen vorzufinden sind. Melanozyten enthalten als cha rakteristische Zellorganellen Melanosomen, die bei Anregung durch UV-Strahlung verstärkt Melanin bilden. Dieses wird in die Hornzellen (Keratinozyten) transportiert und ruft eine mehr oder weniger ausgeprägte bräunliche oder braune Hautfarbe hervor. Responsible for the pigmentation of the skin are the melanocytes, which are in the lowest layer of the epidermis, the stratum basale, in addition to the basal cells as - Depending on the skin type, either isolated or more or less frequent Tende pigment-forming cells are found. Melanocytes contain as cha characteristic cell organelles melanosomes that are excited by ultraviolet radiation increasingly form melanin. This is transported into the horny cells (keratinocytes) and gets a more or less pronounced brownish or brown skin color out.
Melanin wird als Endstufe eines oxidativen Prozesses gebildet, in welchem Tyrosin unter Mitwirkung des Enzymes Tyrosinase über 3,4-Dihydroxyphenylalanin (Dopa), Dopa-Chinon, Leucodopachrom, Dopachrom, 5,6-Dihydroxyindol und Indol-5,6- chinon schließlich in Melanin umgewandelt wird.Melanin is formed as the final stage of an oxidative process in which tyrosine with the participation of the enzyme tyrosinase over 3,4-dihydroxyphenylalanine (Dopa), Dopa-quinone, leucodopachrom, dopachrome, 5,6-dihydroxyindole and indole-5,6- Finally, quinone is converted into melanin.
Probleme mit Hyperpigmentierung der Haut haben vielfältige Ursachen bzw. sind Begleiterscheinungen vieler biologischer Vorgänge, z. B. UV-Strahlung (z. B. Som mersprossen, Ephelides), genetische Disposition, Fehlpigmentierung der Haut bei der Wundheilung bzw. -vernarbung oder der Hautalterung (z. B. Lentigines seni les).Problems with hyperpigmentation of the skin have many causes or are Concomitants of many biological processes, eg. B. UV radiation (eg, Som freckles, ephelides), genetic disposition, skin pigmentation wound healing or scarring or skin aging (eg Lentigines seni les).
Es sind Wirkstoffe und Zubereitungen bekannt, welche der Hautpigmentierung entgegenwirken. Im praktischen Gebrauch sind im wesentlichen Präparate auf der Grundlage von Hydrochinon, welche aber einesteils erst nach mehrwöchiger Anwendung ihre Wirkung zeigen, deren übertrieben lange Anwendung anderer seits aus toxikologischen Gründen bedenklich ist. Auch die Inhibierung der Ty rosinase mit Substanzen wie Kojisäure, Ascorbinsäure und Azelainsäure sowie de ren Derivaten ist geläufig, hat aber kosmetische und dermatologische Nachteile.There are known active ingredients and preparations which skin pigmentation counteract. In practical use are essentially preparations on the Basis of hydroquinone, which, however, partly after several weeks Application show their effect, their over-long use of others On the other hand, it is questionable for toxicological reasons. Also, the inhibition of Ty rosinase with substances such as kojic acid, ascorbic acid and azelaic acid and de ren derivatives is common, but has cosmetic and dermatological disadvantages.
Diesem Übelstande abzuhelfen, war Aufgabe der vorliegenden Erfindung.To remedy this situation was the object of the present invention.
Es ist bekannt, daß Ferulasäure (4-Hydroxy-3-methoxyzimtsäure, Kaffeesäure-3- methylether) antioxidative Eigenschaften hat. Sie ist durch die StrukturformelIt is known that ferulic acid (4-hydroxy-3-methoxycinnamic acid, caffeic acid-3 methyl ether) has antioxidant properties. It is through the structural formula
gekennzeichnet. Sie ist in Pflanzen weit verbreitet und kommt z. B. in Rüben, Ge treide und dem Milchsaft der namensgebenden Doldenblütlern Ferula asafoetida und Ferula nartex vor. Die E-Form ist unter Normalbedingungen ein farblos-kristal liner Festkörper, die Z-Form liegt unter Normalbedingen als gelbliches Öl vor.characterized. It is widespread in plants and comes z. In turnips, Ge treid and the milky sap of the eponymous Umbelliferae Ferula asafoetida and Ferula nartex before. The E-form is a colorless-crystal under normal conditions liner solid, the Z-form is under normal conditions as a yellowish oil.
Die Tocopherole und ihre Ester mit Vitamin-E-Wirksamkeit leiten sich vom Grund körper Tocol ((2-Methyl-2-(4,8,12-trimethyltridecyl)chroman-6-ol) ab und sind durch folgende Strukturen gekennzeichnet:The tocopherols and their esters with vitamin E activity derive from the reason body tocol ((2-methyl-2- (4,8,12-trimethyltridecyl) chroman-6-ol) and are characterized by the following structures are marked:
Dabei stellt K entweder H oder einen Acylrest dar, R, R′ und R′′ bedeuten unab
hängig voneinander H oder eine Methylgruppe, z. B.:
R = R′ = R′′ = K = H: Tocol
R = R′ = R′′ = Methyl, K = H: α-Tocopherol
R = R′′ = Methyl, R′ = K = H: β-Tocopherol
R′ = R′′ = Methyl, R = K = H: γ-Tocopherol
R′′ Methyl, R = R′ = K = H: δ-Tocopherol
R = Methyl, R′ = R′′ = K = H: ε-Tocopherol
R = R′ = Methyl, R′′ = K = H: ζ-Tocopherol
R′ = Methyl, R = R′′ = K = H: η-Tocopherol.In this case, K is either H or an acyl radical, R, R 'and R "are independently of one another H or a methyl group, eg. B .:
R = R '= R "= K = H: tocol
R = R '= R "= methyl, K = H: α-tocopherol
R = R "= methyl, R '= K = H: β-tocopherol
R '= R "= methyl, R = K = H: γ-tocopherol
R '' is methyl, R = R '= K = H: δ-tocopherol
R = methyl, R '= R "= K = H: ε-tocopherol
R = R '= methyl, R "= K = H: ζ-tocopherol
R '= methyl, R = R "= K = H: η-tocopherol.
Dem natürlich am häufigsten vorkommenden und bedeutendsten α-Tocopherol kommt die Konfiguration 2R,4′R,8′R zu. Es wird gelegentlich auch RRR-α-Toco pherol genannt.Of course, the most abundant and important α-tocopherol comes the configuration 2R, 4'R, 8'R. It also occasionally becomes RRR-α-Toco called pherol.
Tocopherylferulat zeichnet sich, entsprechend den isomeren Formen der Femla säure bzw. der verschiedenen Tocopherolgrundkörper durch die StrukturformelnTocopheryl ferulate is characterized according to the isomeric forms of the femla acid or the various tocopherol basic body by the structural formulas
bzw.or.
aus, wobei R, R′ und R′′ den vorstehenden Definitionen gehorchen.where R, R 'and R "are as defined above.
Die Herstellung des Tocopherylferulates und seine Eigenschaften werden in der JP-OS Sho-60/222476 bzw. in der dazugehörigen JP-AS 86/052151 der Gesell schaft Ichimaru Pharcos KK, Japan, beschrieben. Insbesondere wird am ange gebenen Orte auf die kosmetische Verwendbarkeit des Tocopherylferulates bzw. seine Eigenschaft als Antioxidans hingewiesen.The production of tocopheryl ferulate and its properties are described in the JP-OS Sho-60/222476 or in the associated JP-AS 86/052151 the Gesell Ichimaru Pharcos KK, Japan. In particular, is on am given places on the cosmetic usability of tocopheryl or noted its property as an antioxidant.
Vielmehr war überraschend und für den Fachmann nicht vorherzusehen, daß die Verwendung von Tocopherylferulat gegen unerwünschte Pigmentierung der Haut bzw. die Verwendung kosmetischer oder dermatologischer Zubereitungen mit ei nem wirksamen Gehalt an Tocopherylferulat gegen unerwünschte Pigmentierung der Haut, den Nachteilen des Standes der Technik abhelfen.Rather, it was surprising and not foreseeable for the skilled person that the Use of tocopheryl ferulate against unwanted pigmentation of the skin or the use of cosmetic or dermatological preparations with egg effective content of tocopheryl ferulate against unwanted pigmentation the skin, the disadvantages of the prior art remedy.
Tocopherylferulat, hernach, ungeachtet, ob eine Einzelsubstanz oder ein Isome rengemisch oder ein Gemisch verschiedener Tocopherylferulate vorliegt, kollektiv auch "der erfindungsgemäß verwendete Wirkstoff" genannt, hat sich als hervorra gender Wirkstoff gegen unerwünschte Pigmentierung, insbesondere lokale Hyper pigmentierung sowie gegen die durch UV-Strahlung hervorgerufene Haut bräunung, und zwar sowohl präventiv wie auch im Sinne einer Behandlung, erwie sen.Tocopheryl ferulate, hereinafter, whether a single substance or an isome mixture or a mixture of different tocopheryl ferulates, collectively also called "the active ingredient used in the invention", has been hervorra gender active ingredient against unwanted pigmentation, especially local hyper pigmentation and against UV-induced skin tanning, both preventatively and in terms of treatment sen.
Das erfindungsgemäß bevorzugte α-Tocopherylferulat (synonym: Vitamin E-Feru lat, chemisch: 4-Hydroxy-3-methoxyzimtsäure-(2′,5′,7′,8′-tetramethyl-2′-(4′′,8′′,12-′′- trimethyltridecyl)-6′-chromanylester, auch 2,5,7,8-Tetramethyl-2-(4′,8′, 12′-trimethyl tridecyl)-6-Ch romanol-(4′′-hyd roxy-3′′-methoxycinnamat) wird in den Chemical Abstracts unter der Registraturnummer 21290-29-9, vormals 17175-56-3, geführt.The inventively preferred α-tocopheryl ferulate (synonym: vitamin E Feru lat, chemical: 4-hydroxy-3-methoxycinnamic acid (2 ', 5', 7 ', 8'-tetramethyl-2' - (4 '', 8 '', 12 '' ') trimethyltridecyl) -6'-chromanyl ester, also 2,5,7,8-tetramethyl-2- (4 ', 8', 12'-trimethyl tridecyl) -6-Ch romanol (4 "-hydroxy-3" -methoxycinnamate) is disclosed in the Chemical Abstracts under the registry number 21290-29-9, formerly 17175-56-3, out.
Insbesondere bevorzugt ist das DL-α-Tocopherylferulat. Gleichermaßen vorteilhaft sind dabei Isomere mit E- und Z-Konfiguration am Ferulasäurerest.Especially preferred is DL-α-tocopheryl ferulate. Equally advantageous are isomers with E and Z configuration on Ferulasäurerest.
Wenn möglicherweise in der JP-OS Sho-60/222476 bzw. in der dazugehörigen JP-AS 86/052151 nicht für alle denkbaren, im Sinne der vorliegenden Erfindung vorteilhaft zu verwendenden Tocopherylferulate ein konkreter Syntheseweg be schrieben sein möchte, so weiß der Fachmann doch, wie er anhand der Angaben in jenen Schriften und im übrigen auch aufgrund seines allgemeinen Fachwissens zu den gewünschten Individuen gelangen kann, beispielsweise, indem er in dem betreffenden Syntheseschritt das konkret offenbarte Tocopherol als Ausgangsstoff gegen ein möglicherweise nicht konkret offenbartes Tocopherol als Ausgangsstoff austauscht und ansonsten analog verfährt.If possibly in JP-OS Sho-60/222476 or in the associated JP-AS 86/052151 not for all conceivable, for the purposes of the present invention advantageous to use tocopheryl ferulate a concrete synthesis path be wanted to be written, the expert knows how he based on the information in those writings and, moreover, also because of his general expertise to the desired individuals, for example, by having in the relevant synthesis step the specifically disclosed tocopherol as starting material against a possibly not specifically disclosed tocopherol as starting material exchanges and otherwise proceeds in the same way.
Entsprechend der Konfiguration des Ferulasäurerestes ergeben sich für die erfin dungsgemäß bevorzugten Substanzen die StrukturenAccording to the configuration of the Ferulasäurerestes arise for the inventions According to the preferred substances, the structures
bzw.or.
wobei die Konfiguration der Asymmetriezentren am Tocopherylrest nicht berück sichtigt wurde.the configuration of the asymmetric centers on the tocopheryl radical is not taken into account was considered.
Erfindungsgemäß kann der Gehalt an erfindungsgemäß verwendetem Wirkstoff in den kosmetischen oder topischen dermatologischen Zubereitungen 0,01-10 Gew.-%, bevorzugt 0,1-5 Gew.-%, insbesondere 0,2-2,0 Gew.-% betragen, bezogen auf das Gesamtgewicht der Zubereitungen.According to the invention, the content of active ingredient used in accordance with the invention may be in cosmetic or topical dermatological preparations 0.01-10 Wt .-%, preferably 0.1-5 wt .-%, in particular 0.2-2.0 wt .-% amount, based on the total weight of the preparations.
Es hat sich überraschenderweise herausgestellt, daß der erfindungsgemäß ver wendete Wirkstoff die der Erfindung zugrundeliegenden Aufgaben erfüllt. Bei Anwendung des erfindungsgemäß verwendeten Wirkstoffes bzw. kosmetischer oder topischer dermatologischer Zubereitungen mit einem wirksamen Gehalt an erfindungsgemäß verwendetem Wirkstoff ist eine wirksame Prophylaxe gegen unerwünschte Pigmentierung, also beispielsweise die Verhinderung uner wünschter Pigmentierung durch Einwirkung von UV-Strahlung möglich. Es ist aber auch erfindungsgemäß äußerst vorteilhaft, den erfindungsgemäß verwendeten Wirkstoff bzw. kosmetische oder topische dermatologische Zubereitungen mit einem wirksamen Gehalt an erfindungsgemäß verwendetem Wirkstoff zur kosmetischen oder dermatologischen Behandlung unerwünschter Hautpig mentierung, also beispielsweise Lentigines seniles, zu verwenden.It has surprisingly been found that the invention ver used drug meets the underlying tasks of the invention. at Application of the active ingredient used according to the invention or cosmetic or topical dermatological preparations with an effective content Active ingredient used in the invention is an effective prophylaxis against unwanted pigmentation, so for example the prevention uner desired pigmentation by the action of UV radiation possible. But it is Also according to the invention extremely advantageous, the invention used Active substance or cosmetic or topical dermatological preparations with an effective content of active ingredient used according to the invention cosmetic or dermatological treatment of unwanted skin mentation, for example Lentigines seniles.
Die Prophylaxe bzw. die kosmetische oder dermatologische Behandlung mit dem erfindungsgemäß verwendeten Wirkstoff bzw. mit den kosmetischen oder topi schen dermatologischen Zubereitungen mit einem wirksamen Gehalt an erfin dungsgemäß verwendetem Wirkstoff erfolgt in der üblichen Weise, und zwar dergestalt, daß der erfindungsgemäß verwendete Wirkstoff bzw. die kosmetischen oder topischen dermatologischen Zubereitungen mit einem wirksamen Gehalt an erfindungsgemäß verwendetem Wirkstoff auf die betroffenen Hautstellen aufgetragen wird.The prophylaxis or the cosmetic or dermatological treatment with the Active ingredient used according to the invention or with the cosmetic or topical dermatological preparations with an effective content of The active ingredient used in the usual way, namely in such a way that the active ingredient used according to the invention or the cosmetic or topical dermatological preparations with an effective content Active ingredient used in the invention on the affected skin is applied.
Vorteilhaft kann der erfindungsgemäß verwendete Wirkstoff eingearbeitet werden in übliche kosmetische und dermatologische Zubereitungen, welche in ver schiedenen Formen vorliegen können. So können sie z. B. eine Lösung, eine Emulsion vom Typ Wasser-in-Öl (W/O) oder vom Typ Öl-in-Wasser (O/W), oder eine multiple Emulsionen, beispielsweise vom Typ Wasser-in-Öl-in-Wasser (W/O/W) oder Öl-in-Wasser-in-Öl (O/W/O), eine Hydrodispersion oder Lipodis persion, ein Gel, einen festen Stift oder auch ein Aerosol darstellen.Advantageously, the active ingredient used in the invention can be incorporated in conventional cosmetic and dermatological preparations, which in ver different forms may exist. So they can z. B. a solution, a Water-in-oil (W / O) or oil-in-water (O / W) type emulsion, or a multiple emulsions, for example of the water-in-oil-in-water type (W / O / W) or oil-in-water-in-oil (O / W / O), a hydrodispersion or Lipodis persion, a gel, a solid stick or even an aerosol.
Erfindungsgemäße Emulsionen im Sinne der vorliegenden Erfindung, z. B. in Form einer Creme, einer Lotion, einer kosmetischen Milch sind vorteilhaft und enthalten z. B. Fette, Öle, Wachse und/oder andere Fettkörper, sowie Wasser und einen oder mehrere Emulgatoren, wie sie üblicherweise für einen solchen Typ der For mulierung verwendet werden.According to the invention emulsions, z. B. in shape a cream, a lotion, a cosmetic milk are beneficial and included z. As fats, oils, waxes and / or other fatty substances, and water and a or more emulsifiers, as is customary for such a type of For be used.
Es ist auch möglich und vorteilhaft im Sinne der vorliegenden Erfindung, den erfin dungsgemäß verwendeten Wirkstoff in wäßrige Systeme bzw. Tensidzuberei tungen zur Reinigung der Haut und der Haare einzufügen.It is also possible and advantageous within the meaning of the present invention, the inventions used according to the active ingredient in aqueous systems or Tensidzuberei to cleanse the skin and hair.
Es ist dem Fachmanne natürlich bekannt, daß anspruchsvolle kosmetische Zu sammensetzungen zumeist nicht ohne die üblichen Hilfs- und Zusatzstoffe denkbar sind. Darunter zählen beispielsweise Konsistenzgeber, Füllstoffe, Parfum, Farbstoffe, Emulgatoren, zusätzliche Wirkstoffe wie Vitamine oder Proteine, Lichtschutzmittel, Stabilisatoren, Insektenrepellentien, Alkohol, Wasser, Salze, antimikrobiell, proteolytisch oder keratolytisch wirksame Substanzen usw.It is well known to those skilled in the art that sophisticated cosmetic applications compositions usually not without the usual auxiliaries and additives are conceivable. These include, for example, bodying agents, fillers, perfume, Dyes, emulsifiers, additional active ingredients such as vitamins or proteins, Light stabilizers, stabilizers, insect repellents, alcohol, water, salts, antimicrobial, proteolytic or keratolytic substances, etc.
Mutatis mutandis gelten entsprechende Anforderungen an die Formulierung medi zinischer Zubereitungen.Mutatis mutandis, corresponding requirements apply to the formulation medi Zinc preparations.
Medizinische topische Zusammensetzungen im Sinne der vorliegenden Erfindung enthalten in der Regel ein oder mehrere Medikamente in wirksamer Konzentration. Der Einfachheit halber wird zur sauberen Unterscheidung zwischen kosmetischer und medizinischer Anwendung und entsprechenden Produkten auf die gesetzlichen Bestimmungen der Bundesrepublik Deutschland verwiesen (z. B. Kosmetikverordnung Lebensmittel- und Arzneimittelgesetz).Medical topical compositions according to the present invention usually contain one or more drugs in effective concentration. For the sake of simplicity, a clear distinction between cosmetic and medical application and related products to the referred to in the statutory provisions of the Federal Republic of Germany (eg Cosmetics Regulation Food and Drug Law).
Es ist dabei ebenfalls von Vorteil, den erfindungsgemäß verwendeten Wirkstoff als Zusatzstoff zu Zubereitungen zu geben, die bereits andere Wirkstoffe für andere Zwecke enthalten.It is also advantageous to use the active ingredient according to the invention as Add additive to preparations that already have other active ingredients for others Purposes included.
Entsprechend können kosmetische oder topische dermatologische Zusammenset zungen im Sinne der vorliegenden Erfindung, je nach ihrem Aufbau, bei spielsweise verwendet werden als Hautschutzcr´me, Reinigungsmilch, Sonnen schutzlotion, Nährcr´me, Tages- oder Nachtcr´me usw. Es ist gegebenenfalls möglich und vorteilhaft, die erfindungsgemäßen Zusammensetzungen als Grundlage für pharmazeutische Formulierungen zu verwenden.Accordingly, cosmetic or topical dermatological composition according to the present invention, depending on their structure, at For example, be used as Hautschutzcr'me, cleansing milk, sun protective lotion, nutrients, day or night creams, etc. It is optional possible and advantageous, the compositions of the invention as Basis for pharmaceutical formulations.
Günstig sind gegebenenfalls auch solche kosmetischen und dermatologischen Zu bereitungen, die in der Form eines Sonnenschutzmittels vorliegen. Vorzugsweise enthalten diese neben dem erfindungsgemäß verwendeten Wirkstoff zusätzlich mindestens eine UVA-Filtersubstanz und/oder mindestens eine UVB-Fil tersubstanz und/oder mindestens ein anorganisches Pigment.If appropriate, such cosmetic and dermatological additives are also favorable preparations which are in the form of a sunscreen. Preferably contain these in addition to the active ingredient used in the invention additionally at least one UVA filter substance and / or at least one UVB film tersubstanz and / or at least one inorganic pigment.
Es ist aber auch vorteilhaft im Sinne der vorliegenden Erfindungen, solche kosme tischen und dermatologischen Zubereitungen zu erstellen, deren hauptsächlicher Zweck nicht der Schutz vor Sonnenlicht ist, die aber dennoch einen Gehalt an UV- Schutzsubstanzen enthalten. So werden beispielsweise in Tagescr´mes gewöhn lich UV-A- bzw. UV-B-Filtersubstanzen eingearbeitet.But it is also advantageous in the sense of the present inventions, such kosme tables and dermatological preparations, the main ones of which are The purpose is not to protect against sunlight, but Contains protective substances. For example, getting used to day crèmes incorporated UV-A or UV-B filter substances.
Vorteilhaft können erfindungsgemäße Zubereitungen Substanzen enthalten, die UV-Strahlung im UVB-Bereich absorbieren, wobei die Gesamtmenge der Filtersub stanzen z. B. 0,1 Gew.-% bis 30 Gew.-%, vorzugsweise 0,5 bis 10 Gew.-%, insbe sondere 1 bis 6 Gew.-% beträgt, bezogen auf das Gesamtgewicht der Zuberei tungen.Advantageously, preparations according to the invention may contain substances which Absorb UV radiation in the UVB range, the total amount of the filterub punching z. B. 0.1 wt .-% to 30 wt .-%, preferably 0.5 to 10 wt .-%, in particular especially 1 to 6 wt .-%, based on the total weight of Zuberei obligations.
Die UVB-Filter können öllöslich oder wasserlöslich sein. Als öllösliche Substanzen sind z. B. zu nennen:The UVB filters may be oil-soluble or water-soluble. As oil-soluble substances are z. To name, for example:
- - 3-Benzylidencampher und dessen Derivate, z. B. 3-(4-Methylbenzyliden)cam pher,- 3-Benzylidencampher and its derivatives, for. B. 3- (4-methylbenzylidene) cam pher,
- - 4-Aminobenzoäsäure-Derivate, vorzugsweise 4-(Dimethylamino)-benzoesäu re(2-ethylhexyl)ester, 4-(Dimethylamino)benzoesäureamylester;4-aminobenzoic acid derivatives, preferably 4- (dimethylamino) benzoic acid (2-ethylhexyl) ester, 4- (dimethylamino) benzoic acid amyl ester;
- - Ester der Zimtsäure, vorzugsweise 4-Methoxyzimtsäure(2-ethylhexyl)ester, 4-Methoxyzimtsäureisopentylester;Esters of cinnamic acid, preferably 4-methoxycinnamic acid (2-ethylhexyl) ester, 4-methoxycinnamate;
- - Ester der Salicylsäure, vorzugsweise Salicylsäure(2-ethylhexyl)ester, Salicyl säure(4-isopropylbenzyl)ester, Salicylsäurehomomenthylester;- Salicylic acid esters, preferably 2-ethylhexyl salicylate, salicylic acid (4-isopropylbenzyl) ester, salicylic acid homomenthyl ester;
- - Derivate des Benzophenons, vorzugsweise 2-Hydroxy-4-methoxybenzophe non, 2-Hydroxy-4-methoxy-4′-methylbenzophenon, 2,2′-Dihydroxy-4-meth oxybenzophenon;- Derivatives of benzophenone, preferably 2-hydroxy-4-methoxybenzophe non, 2-hydroxy-4-methoxy-4'-methylbenzophenone, 2,2'-dihydroxy-4-meth oxybenzophenone;
- - Ester der Benzalmalonsäure, vorzugsweise 4-Methoxybenzalmalon säuredi(2-ethylhexyl)ester;Esters of benzalmalonic acid, preferably 4-methoxybenzalmalone säuredi (2-ethylhexyl) ester;
- - 2,4,6-Trianilino-(p-carbo-2′-ethyl-1′-hexyloxy)-1,3,5-triazin2,4,6-trianilino (p-carbo-2'-ethyl-1'-hexyloxy) -1,3,5-triazine
Als wasserlösliche Substanzen sind vorteilhaft:As water-soluble substances are advantageous:
- - 2-Phenylbenzimidazol-5-sulfonsäure und deren Salze, z. B. Natrium-, Ka lium- oder Triethanolammonium-Salze,- 2-phenylbenzimidazole-5-sulfonic acid and its salts, eg. For example, sodium, Ka lium or triethanolammonium salts,
- - Sulfonsäure-Derivate von Benzophenonen, vorzugsweise 2-Hydroxy-4-meth oxybenzophenon-5-sulfonsäure und ihre Salze;Sulfonic acid derivatives of benzophenones, preferably 2-hydroxy-4-meth oxybenzophenone-5-sulfonic acid and its salts;
- - Sulfonsäure-Derivate des 3-Benzylidencamphers, wie z. B. 4-(2-Oxo-3-borny lidenmethyl)benzolsulfonsäure, 2-Methyl-5-(2-oxo-3-bornylidenmethyl)sulfon säure und ihre Salze.- Sulfonic acid derivatives of 3-Benzylidencamphers, such as. B. 4- (2-oxo-3-borny lidenmethyl) benzenesulfonic acid, 2-methyl-5- (2-oxo-3-bomylidenemethyl) sulfone acid and its salts.
Die Liste der genannten UVB-Filter, die erfindungsgemäß Verwendung finden kön nen, soll selbstverständlich nicht limitierend sein.The list of said UVB filters which can be used according to the invention of course, should not be limiting.
Gegenstand der Erfindung ist auch die Kombination eines erfindungsgemäßen UVA-Filters mit einem UVB-Filter bzw. eine erfindungsgemäßes kosmetische oder dermatologische Zubereitung, welche auch einen UVB-Filter enthält.The invention also relates to the combination of an inventive UVA filters with a UVB filter or a cosmetic or cosmetic according to the invention dermatological preparation which also contains a UVB filter.
Es kann auch von Vorteil sein, in erfindungsgemäßen Zubereitungen UVA-Filter einzusetzen, die üblicherweise in kosmetischen und/oder dermatologischen Zube reitungen enthalten sind. Bei solchen Filtersubstanzen handelt es sich vor zugsweise um Derivate des Dibenzoylmethans, insbesondere um 1-(4′- tert.Butylphenyl)-3-(4′-methoxyphenyl)propan-1,3-dion und um 1 -Phenyl-3-(4′-iso propylphenyl)propan-1,3-dion. Auch Zubereitungen, die diese Kombinationen enthalten, sind Gegenstand der Erfindung. Es können die gleichen Mengen an UVA-Filtersubstanzen verwendet werden, welche für UVB-Filtersubstanzen genannt wurden.It may also be advantageous in formulations according to the invention UVA filters commonly used in cosmetic and / or dermatological applications are included. Such filter substances are present preferably derivatives of dibenzoylmethane, in particular 1- (4'- tert-butylphenyl) -3- (4'-methoxyphenyl) propane-1,3-dione and 1-phenyl-3- (4'-iso propylphenyl) propan-1,3-dione. Also preparations containing these combinations contain, are the subject of the invention. It can be the same amounts UVA filter substances are used, which for UVB filter substances were called.
Kosmetische und/oder dermatologische Zubereitungen im Sinne der vorliegenden Erfindung können auch anorganische Pigmente enthalten, die üblicherweise in der Kosmetik zum Schutze der Haut vor UV-Strahlen verwendet werden. Dabei handelt es sich um Oxide des Titans, Zinks, Eisens, Zirkoniums, Siliciums, Mangans, Aluminiums, Cers und Mischungen davon, sowie Abwandlungen, bei denen die Oxide die aktiven Agentien sind. Besonders bevorzugt handelt es sich um Pigmente auf der Basis von Titandioxid. Es können die für die vorstehenden Kombinationen genannten Mengen verwendet werden.Cosmetic and / or dermatological preparations within the meaning of the present invention The invention may also include inorganic pigments commonly used in the art Cosmetics are used to protect the skin from UV rays. there are oxides of titanium, zinc, iron, zirconium, silicon, Manganese, aluminum, cerium and mixtures thereof, as well as modifications where the oxides are the active agents. It is particularly preferred pigments based on titanium dioxide. It can be for the above Combinations mentioned quantities can be used.
Die erfindungsgemäßen kosmetischen und dermatologischen Zubereitungen kön nen kosmetische Wirk-, Hilfs- und/oder Zusatzstoffe enthalten, wie sie üblicher weise in solchen Zubereitungen verwendet werden, z. B. Antioxidationsmittel, Kon servierungsmittel, Bakterizide, Parfüme, Substanzen zum Verhindern des Schäumens, Farbstoffe, Pigmente, die färbende Wirkung haben, Verdickungs mittel, oberflächenaktive Substanzen, Emulgatoren, weichmachende, an feuchtende und/oder feuchthaltende Substanzen, Fette, Öle, Wachse oder andere übliche Bestandteile einer kosmetischen oder dermatologischen Formulierung wie Alkohole, Polyole, Polymere, Schaumstabilisatoren, Elektrolyte, organische Lösungsmittel oder Silikonderivate.The cosmetic and dermatological preparations according to the invention can be contain cosmetic active ingredients, auxiliaries and / or additives, as is customary example be used in such preparations, for. B. Antioxidants, Kon Serving agents, bactericides, perfumes, substances for preventing Foaming, dyes, pigments that have coloring properties, thickening medium, surface-active substances, emulsifiers, softening, on moisturizing and / or moisturizing substances, fats, oils, waxes or others usual ingredients of a cosmetic or dermatological formulation such as Alcohols, polyols, polymers, foam stabilizers, electrolytes, organic Solvent or silicone derivatives.
Es ist ebenfalls vorteilhaft, den Zubereitungen im Sinne der vorliegenden Erfin dung übliche Antioxidantien zuzufügen. Erfindungsgemäß können als günstige Antioxidantien alle für kosmetische und/oder dermatologische Anwendungen geeigneten oder gebräuchlichen Antioxidantien verwendet werden.It is also advantageous to the preparations according to the present inven add conventional antioxidants. According to the invention as cheap Antioxidants all for cosmetic and / or dermatological applications suitable or common antioxidants are used.
Vorteilhaft werden die Antioxidantien gewählt aus der Gruppe bestehend aus Ami nosäuren (z. B. Glycin, Histidin, Tyrosin, Tryptophan) und deren Derivate, Imida zole (z. B. Urocaninsäure) und deren Derivate, Peptide wie D,L-Carnosin, D-Car nosin, L-Carnosin und deren Derivate (z. B. Anserin), Carotinoide, Carotine (z. B. α- Carotin, β-Carotin, Lycopin) und deren Derivate, Liponsäure und deren Derivate (z. B. Dihydroliponsäure), Aurothioglucose, Propylthiouracil und andere Thiole (z. B. Thioredoxin, Glutathion, Cystein, Cystin, Cystamin und deren Glycosyl-, N-Acetyl-, Methyl-, Ethyl-, Propyl-, Amyl-, Butyl- und Lauryl-, Palmitoyl-, Oleyl-, γ-Linoleyl-, Cholesteryl- und Glycerylester) sowie deren Salze, Dilaurylthiodipropionat, Distearylthiodipropionat, Thiodipropionsäure und deren Derivate (Ester, Ether, Peptide, Lipide, Nukleotide, Nukleoside und Salze) sowie Sulfoximinverbindungen (z. B. Buthioninsulfoximine, Homocysteinsulfoximin, Buthioninsulfone, Penta-, Hexa-, Heptathioninsulfoximin) in sehr geringen verträglichen Dosierungen (z. B. pmol bis µmol/kg), ferner (Metall)-Chelatoren (z. B. α-Hydroxyfettsäuren, Palmitinsäure, Phytinsäure, Lactoferrin), α-Hydroxysäuren (z. B. Zitronensäure, Milchsäure, Apfelsäure), Huminsäure, Gallensäure, Gallenextrakte, Bilirubin, Bili verdin, EDTA, EGTA und deren Derivate, ungesättigte Fettsäuren und deren Derivate (z. B. γ-Linolensäure, Linolsäure, Ölsäure), Folsäure und deren Derivate, Alanindiessigsäure, Flavonoide, Polyphenole, Catechine, Ubichinon und Ubichinol und deren Derivate, Vitamin C und Derivate (z. B. Ascorbylpalmitat, Mg-Ascor bylphosphat, Ascorbylacetat), Tocopherole und Derivate (z. B. Vitamin-E-acetat), sowie Koniferylbenzoat des Benzoeharzes, Rutinsäure und deren Derivate, Feru lasäure und deren Derivate, Butylhydroxytoluol, Butylhydroxyanisol, Nordihydro guajakharzsäure, Nordihydroguajaretsäure, Trihydroxybutyrophenon, Harnsäure und deren Derivate, Mannose und deren Derivate, Zink und dessen Derivate (z. B. ZnO, ZnSO₄) Selen und dessen Derivate (z. B. Selenmethionin), Stilbene und de ren Derivate (z. B. Stilbenoxid, Trans-Stilbenoxid) und die erfindungsgemäß geeigneten Derivate (Salze, Ester, Ether, Zucker, Nukleotide, Nukleoside, Peptide und Lipide) dieser genannten Wirkstoffe.Advantageously, the antioxidants are selected from the group consisting of amino acids (eg, glycine, histidine, tyrosine, tryptophan) and their derivatives, imida zole (eg, urocanic acid) and derivatives thereof, peptides such as D, L-carnosine, D-car nosin, L-carnosine and their derivatives (eg anserine), carotenoids, carotenes (eg. Carotene, β-carotene, lycopene) and their derivatives, lipoic acid and its derivatives (eg dihydrolipoic acid), aurothioglucose, propylthiouracil and other thiols (e.g. Thioredoxin, glutathione, cysteine, cystine, cystamine and their glycosyl, N-acetyl, Methyl, ethyl, propyl, amyl, butyl and lauryl, palmitoyl, oleyl, γ-linoleyl, Cholesteryl and glyceryl esters) and their salts, dilauryl thiodipropionate, Distearyl thiodipropionate, thiodipropionic acid and its derivatives (esters, ethers, Peptides, lipids, nucleotides, nucleosides and salts) as well as sulfoximine compounds (eg, buthionine sulfoximines, homocysteine sulfoximine, buthionine sulfones, penta-, Hexa-, heptathionine sulfoximine) in very low tolerated dosages (eg. pmol to μmol / kg), furthermore (metal) chelators (for example α-hydroxyfatty acids, Palmitic acid, phytic acid, lactoferrin), α-hydroxy acids (eg citric acid, Lactic acid, malic acid), humic acid, bile acid, bile extracts, bilirubin, bili verdin, EDTA, EGTA and their derivatives, unsaturated fatty acids and their derivatives Derivatives (eg γ-linolenic acid, linoleic acid, oleic acid), folic acid and derivatives thereof, Alaninediacetic acid, flavonoids, polyphenols, catechins, ubiquinone and ubiquinol and their derivatives, vitamin C and derivatives (eg ascorbyl palmitate, Mg-Ascor bylphosphate, ascorbyl acetate), tocopherols and derivatives (eg vitamin E acetate), and coniferyl benzoate of benzoin, rutinic acid and their derivatives, Feru and acid derivatives thereof, butylhydroxytoluene, butylhydroxyanisole, Nordihydro guaiacolic acid, nordihydroguiaretic acid, trihydroxybutyrophenone, uric acid and their derivatives, mannose and derivatives thereof, zinc and its derivatives (eg. ZnO, ZnSO₄) selenium and its derivatives (eg selenomethionine), stilbenes and de ren derivatives (eg stilbene oxide, trans-stilbene oxide) and the invention suitable derivatives (salts, esters, ethers, sugars, nucleotides, nucleosides, peptides and lipids) of these drugs.
Die Menge der Antioxidantien (eine oder mehrere Verbindungen) in den Zuberei tungen beträgt vorzugsweise 0,001 bis 30 Gew.-%, besonders bevorzugt 0,05-20 Gew.-%, insbesondere 1-10 Gew.-%, bezogen auf das Gesamtgewicht der Zube reitung.The amount of antioxidants (one or more compounds) in the bait is preferably 0.001 to 30 wt .-%, particularly preferably 0.05-20 Wt .-%, in particular 1-10 wt .-%, based on the total weight of the Zube reitung.
Sofern Vitamin E und/oder dessen Derivate das oder die Antioxidantien darstellen, ist vorteilhaft, deren jeweilige Konzentrationen aus dem Bereich von 0,001-10 Gew.-%, bezogen auf das Gesamtgewicht der Formulierung, zu wählen. If vitamin E and / or its derivatives are the antioxidant or antioxidants, is advantageous, their respective concentrations in the range of 0.001-10 Wt .-%, based on the total weight of the formulation to choose.
Sofern die kosmetische oder dermatologische Zubereitung im Sinne der vorliegen den Erfindung eine Lösung oder Emulsion oder Dispersion darstellt, können als Lösungsmittel verwendet werden:If the cosmetic or dermatological preparation in the sense of present The invention is a solution or emulsion or dispersion can, as Solvents are used:
- - Wasser oder wäßrige Lösungen- water or aqueous solutions
- - Öle, wie Triglyceride der Caprin- oder der Caprylsäure, vorzugsweise aber Rizinusöl;- Oils, such as triglycerides of capric or caprylic acid, but preferably Castor oil;
- - Fette, Wachse und andere natürliche und synthetische Fettkörper, vor zugsweise Ester von Fettsäuren mit Alkoholen niedriger C-Zahl, z. B. mit Isopropanol, Propylenglykol oder Glycerin, oder Ester von Fettalkoholen mit Alkansäuren niedriger C-Zahl oder mit Fettsäuren;- Fats, waxes and other natural and synthetic fats, before preferably esters of fatty acids with lower C-number alcohols, e.g. B. with Isopropanol, propylene glycol or glycerol, or esters of fatty alcohols with Alkanoic acids of low C number or with fatty acids;
- - Alkohole, Diole oder Polyole niedriger C-Zahl, sowie deren Ether, vorzugs weise Ethanol, Isopropanol, Propylenglykol, Glycerin, Ethylenglykol, Ethy lenglykolmonoethyl- oder -monobutylether, Propylenglykolmonomethyl, - monoethyl- oder -monobutylether, Diethylenglykolmonomethyl- oder - monoethylether und analoge Produkte.- Alcohols, diols or polyols low C number, and their ethers, preferably Example, ethanol, isopropanol, propylene glycol, glycerol, ethylene glycol, ethylene glycol monoethyl or monobutyl ether, propylene glycol monomethyl, monoethyl or monobutyl ether, diethylene glycol monomethyl or - monoethyl ether and analog products.
Insbesondere werden Gemische der vorstehend genannten Lösungsmittel verwen det. Bei alkoholischen Lösungsmitteln kann Wasser ein weiterer Bestandteil sein.In particular, mixtures of the abovementioned solvents verwen det. For alcoholic solvents, water can be another ingredient.
Die Ölphase der Emulsionen, Oleogele bzw. Hydrodispersionen oder Lipodispersi onen im Sinne der vorliegenden Erfindung wird vorteilhaft gewählt aus der Gruppe der Ester aus gesättigten und/oder ungesättigten, verzweigten und/oder unver zweigten Alkancarbonsäuren einer Kettenlänge von 3 bis 30 C-Atomen und gesät tigten und/oder ungesättigten, verzweigten und/oder unverzweigten Alkoholen ei ner Kettenlänge von 3 bis 30 C-Atomen, aus der Gruppe der Ester aus aromatischen Carbonsäuren und gesättigten und/oder ungesättigten, verzweigten und/oder unverzweigten Alkoholen einer Kettenlänge von 3 bis 30 C-Atomen. Solche Esteröle können dann vorteilhaft gewählt werden aus der Gruppe Isopropylmyristat, Isopropylpalmitat, Isopropylstearat, Isopropyloleat, n-Butylstearat, n-Hexyllaurat, n-Decyloleat, Isooctylstearat, Isönonylstearat, Isc nonylisononanoat, 2-Ethylhexylpalmitat, 2-Ethylhexyllaurat, 2-HexyldecyIstearat, 2- Octyldodecylpalmitat, Oleyloleat, Oleylerucat, Erucyloleat, Erucylerucat sowie syn thetische, halbsynthetische und natürliche Gemische solcher Ester, z. B. Jojobaöl. The oil phase of the emulsions, oleogels or hydrodispersions or Lipodispersi Ones in the context of the present invention is advantageously selected from the group the ester of saturated and / or unsaturated, branched and / or unreacted branched alkanecarboxylic acids of a chain length of 3 to 30 carbon atoms and sown ei and / or unsaturated, branched and / or unbranched alcohols ei ner chain length of 3 to 30 carbon atoms, from the group of esters aromatic carboxylic acids and saturated and / or unsaturated, branched and / or unbranched alcohols of a chain length of 3 to 30 carbon atoms. Such ester oils can then be advantageously selected from the group Isopropyl myristate, isopropyl palmitate, isopropyl stearate, isopropyl oleate, n-butyl stearate, n-hexyl laurate, n-decyl oleate, isooctyl stearate, isononyl stearate, Isc nonyl isononanoate, 2-ethylhexyl palmitate, 2-ethylhexyl laurate, 2-hexyldecyl stearate, 2- Octyl dodecyl palmitate, oleyl oleate, oleyl erucate, erucyl oleate, erucyl erucate and syn thetic, semi-synthetic and natural mixtures of such esters, e.g. B. jojoba oil.
Ferner kann die Ölphase vorteilhaft gewählt werden aus der Gruppe der ver zweigten und unverzweigten Kohlenwasserstoffe und -wachse, der Silkonöle, der Dialkylether, der Gruppe der gesättigten oder ungesättigten, verzweigten oder un verzweigten Alkohole, sowie der Fettsäuretriglyceride, namentlich der Triglycerin ester gesättigter und/oder ungesättigter, verzweigter und/oder unverzweigter Al kancarbonsäuren einer Kettenlänge von 8 bis 24, insbesondere 12-18 C-Atomen. Die Fettsäuretriglyceride können beispielsweise vorteilhaft gewählt werden aus der Gruppe der synthetischen, halbsynthetischen und natürlichen Öle, z. B. Olivenöl, Sonnenblumenöl, Sojaöl, Erdnußöl, Rapsöl, Mandelöl, Palmöl, Kokosöl, Palmkernöl und dergleichen mehr.Furthermore, the oil phase can be advantageously selected from the group of ver Branched and unbranched hydrocarbons and waxes, of silicone oils, Dialkyl ethers, the group of saturated or unsaturated, branched or un branched alcohols, as well as the fatty acid triglycerides, namely the triglycerol esters of saturated and / or unsaturated, branched and / or unbranched Al kancarbonsäuren a chain length of 8 to 24, in particular 12-18 C-atoms. The fatty acid triglycerides can be selected, for example, advantageously from Group of synthetic, semi-synthetic and natural oils, e.g. Olive oil, Sunflower oil, soybean oil, peanut oil, rapeseed oil, almond oil, palm oil, coconut oil, Palm kernel oil and the like more.
Auch beliebige Abmischungen solcher Öl- und Wachskomponenten sind vorteil haft im Sinne der vorliegenden Erfindung einzusetzen. Es kann auch gegebenen falls vorteilhaft sein, Wachse, beispielsweise Cetylpalmitat, als alleinige Lipid komponente der Ölphase einzusetzen.Any mixtures of such oil and wax components are advantageous to use for the purposes of the present invention. It can also be given if advantageous, waxes, for example cetyl palmitate, as the sole lipid component of the oil phase.
Vorteilhaft wird die Ölphase gewählt aus der Gruppe 2-Ethylhexylisostearat, Octyl dodecanol, Isotridecylisononanoat, Isoeicosan, 2-Ethylhexylcocoat, C12-15-Alkyl benzoat, Capryl-Caprinsäure-triglycerid, Dicaprylylether.Advantageously, the oil phase is selected from the group consisting of 2-ethylhexyl isostearate, octyl dodecanol, isotridecyl isononanoate, isoeicosane, 2-ethylhexyl cocoate, C 12-15 alkyl benzoate, caprylic capric acid triglyceride, dicaprylyl ether.
Besonders vorteilhaft sind Mischungen aus C12-15-Alkybenzoat und 2-Ethylhexyl isostearat, Mischungen aus C12-15-Alkybenzoat und Isotridecylisononanoat sowie Mischungen aus C12-15-Alkybenzoat, 2-Ethylhexylisostearat und Isotridecyliso nonanoat.Particularly advantageous are mixtures of C 12-15 -alkyl benzoate and 2-ethylhexyl isostearate, mixtures of C 12-15 -alkyl benzoate and Isotridecylisononanoat and mixtures of C 12-15 -alkyl benzoate, 2-Ethylhexylisostearat and Isotridecyliso nonanoate.
Von den Kohlenwasserstoffen sind Paraffinöl, Squalan und Squalen vorteilhaft im Sinne der vorliegenden Erfindung zu verwenden.Of the hydrocarbons, paraffin oil, squalane and squalene are beneficial in the Use of the present invention.
Vorteilhaft kann die Ölphase ferner einen Gehalt an cyclischen oder linearen Sili konölen aufweisen oder vollständig aus solchen Ölen bestehen, wobei allerdings bevorzugt wird, außer dem Silikonöl oder den Silikonölen einen zusätzlichen Gehalt an anderen Ölphasenkomponenten zu verwenden.Advantageously, the oil phase may further contain cyclic or linear silicates have or consist entirely of such oils, although is preferred, except the silicone oil or silicone oils an additional To use content of other oil phase components.
Vorteilhaft wird Cyclomethicon (Octamethylcyclotetrasiloxan) als erfindungsgemäß zu verwendendes Silikonöl eingesetzt. Aber auch andere Silikonöle sind vorteilhaft im Sinne der vorliegenden Erfindung zu verwenden, beispielsweise Hexamethylcy clotrisiloxan Polydimethylsiloxan, Poly(methylphenylsiloxan).Cyclomethicone (octamethylcyclotetrasiloxane) is advantageous according to the invention used to be used silicone oil. But other silicone oils are beneficial for the purposes of the present invention, for example Hexamethylcy clotrisiloxane polydimethylsiloxane, poly (methylphenylsiloxane).
Besonders vorteilhaft sind ferner Mischungen aus Cyclomethicon und Isotridecyl isononanoat, aus Cyclomethicon und 2-Ethylhexylisostearat.Also particularly advantageous are mixtures of cyclomethicone and isotridecyl isononanoate, from cyclomethicone and 2-ethylhexyl isostearate.
Erfindungsgemäß verwendete Gele enthalten üblicherweise Alkohole niedriger C- Zahl z. B. Ethanol, Isopropanol, 1,2-Propandiol, Glycerin und Wasser bzw. ein vor stehend genanntes Öl in Gegenwart eines Verdickungsmittels, das bei ölig-alkoho lischen Gelen vorzugsweise Siliciumdioxid oder ein Aluminiumsilikat, bei wäßrig-al koholischen oder alkoholischen Gelen vorzugsweise ein Polyacrylat ist.Gels used according to the invention usually contain lower C alcohols. Number z. As ethanol, isopropanol, 1,2-propanediol, glycerol and water or a before standing oil in the presence of a thickener, the oily-alkoho gels preferably silica or an aluminum silicate, in aqueous-al or alcoholic gels, preferably a polyacrylate.
Feste Stifte enthalten z. B. natürliche oder synthetische Wachse, Fettalkohole oder Fettsäureester. Bevorzugt werden Lippenpflegestifte sowie Stiftformulierungen zur Körperdesodorierung.Fixed pins contain z. As natural or synthetic waxes, fatty alcohols or Fatty acid ester. Lip balm sticks and stick formulations are preferred Körperdesodorierung.
Übliche Grundstoffe, welche für die Verwendung als kosmetische Stifte im Sinne der vorliegenden Erfindung geeignet sind, sind flüssige Öle (z. B. Paraffinöle, Ri cinusöl, Isopropylmyristat), halbfeste Bestandteile (z. B. Vaseline, Lanolin), feste Bestandteile (z. B. Bienenwachs, Ceresin und Mikrokristalline Wachse bzw. Ozo kerit) sowie hochschmelzende Wachse (z. B. Carnaubawachs, Candelillawachs).Usual raw materials, which are intended for use as cosmetic sticks in the sense of the present invention, liquid oils (e.g., paraffin oils, Ri cinus oil, isopropyl myristate), semi-solid components (eg petrolatum, lanolin), solid Ingredients (eg beeswax, ceresin and microcrystalline waxes or ozo kerit) and high-melting waxes (eg carnauba wax, candelilla wax).
Als Treibmittele für aus Aerosolbehältern versprühbare kosmetische und/oder der matologische Zubereitungen im Sinne der vorliegenden Erfindung sind die üblichen bekannten leichtflüchtigen, verflüssigten Treibmittel, beispielsweise Kohlenwasserstoffe (Propan, Butan, Isobutan) geeignet, die allein oder in Mi schung miteinander eingesetzt werden können. Auch Druckluft ist vorteilhaft zu verwenden.As propellant for sprayable from aerosol containers cosmetic and / or the Matological preparations in the context of the present invention are the customary known volatile, liquefied propellant, for example Hydrocarbons (propane, butane, isobutane) suitable alone or in Mi can be used together. Also compressed air is beneficial too use.
Natürlich weiß der Fachmann, daß es an sich nichttoxische Treibgase gibt, die grundsätzlich für die Verwirklichung der vorliegenden Erfindung in Form von Aera solpräparaten geeignet wären, auf die aber dennoch wegen bedenklicher Wirkung auf die Umwelt oder sonstiger Begleitumstände verzichtet werden sollte, insbeson dere Fluorkohlenwasserstoffe und Fluorchlorkohlenwasserstoffe (FCKW). Of course, the person skilled in the art knows that there are nontoxic propellants per se which basically for the realization of the present invention in the form of aera solpräparaten would be suitable, but nevertheless because of questionable effect the environment or other accompanying circumstances should be waived, esp hydrofluorocarbons and chlorofluorocarbons (CFCs).
Kosmetische Zubereitungen im Sinne der vorliegenden Erfindung können auch als Gele vorliegen, die neben einem wirksamen Gehalt am erfindungsgemäßen Wirk stoff und dafür üblicherweise verwendeten Lösungsmitteln, bevorzugt Wasser, noch organische Verdickungsmittel, z. B. Gummiarabikum, Xanthangummi, Na triumalginat, Cellulose-Derivate, vorzugsweise Methylcellulose, Hydroxymethylcel lulose, Hydroxyethylcellulose, Hydroxypropylcellulose, Hydroxypropylmethylcellu lose oder anorganische Verdickungsmittel, z. B. Aluminiumsilikate wie beispiels weise Bentonite, oder ein Gemisch aus Polyethylenglykol und Polyethylenglykol stearat oder -distearat, enthalten. Das Verdickungsmittel ist in dem Gel z. B. in einer Menge zwischen 0,1 und 30 Gew.-%, bevorzugt zwischen 0,5 und 15 Gew.-%, enthalten.Cosmetic preparations according to the present invention can also be described as Gels are present, in addition to an effective content of Wirk Wirk substance and solvents commonly used for this purpose, preferably water, still organic thickeners, z. Gum arabic, xanthan gum, Na trium alginate, cellulose derivatives, preferably methylcellulose, hydroxymethylcel cellulose, hydroxyethylcellulose, hydroxypropylcellulose, hydroxypropylmethylcellu loose or inorganic thickeners, e.g. B. aluminum silicates such as Bentonite, or a mixture of polyethylene glycol and polyethylene glycol stearate or distearate. The thickener is in the gel z. In in an amount between 0.1 and 30% by weight, preferably between 0.5 and 15% by weight, contain.
Die nachfolgenden Beispiele sollen die vorliegende Erfindung verdeutlichen.The following examples are intended to illustrate the present invention.
Claims (4)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1996138534 DE19638534A1 (en) | 1996-09-20 | 1996-09-20 | Use of tocopheryl ferulate as skin bleaching agent |
| JP27193497A JPH10120542A (en) | 1996-09-20 | 1997-09-19 | Use of tocopheryl feruliate for making skin less brown and preventing sunburn, in particular that caused by ultraviolet ray |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1996138534 DE19638534A1 (en) | 1996-09-20 | 1996-09-20 | Use of tocopheryl ferulate as skin bleaching agent |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE19638534A1 true DE19638534A1 (en) | 1998-03-26 |
Family
ID=7806311
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1996138534 Withdrawn DE19638534A1 (en) | 1996-09-20 | 1996-09-20 | Use of tocopheryl ferulate as skin bleaching agent |
Country Status (2)
| Country | Link |
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| JP (1) | JPH10120542A (en) |
| DE (1) | DE19638534A1 (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8080583B2 (en) | 2007-07-31 | 2011-12-20 | Elc Management Llc | Emulsion cosmetic compositions containing resveratrol derivatives and linear or branched silicone |
| US8084496B2 (en) | 2007-07-31 | 2011-12-27 | Elc Management Llc | Resveratrol ferulate compounds and compositions |
| US8344024B2 (en) | 2007-07-31 | 2013-01-01 | Elc Management Llc | Anhydrous cosmetic compositions containing resveratrol derivatives |
| US9220669B2 (en) | 2007-09-08 | 2015-12-29 | Elc Management Llc | Resveratrol ferulate compounds, compositions containing the compounds, and methods of using the same |
| US9295621B2 (en) | 2007-07-31 | 2016-03-29 | Elc Management Llc | Emulsion cosmetic compositions containing resveratrol derivatives and silicone surfactant |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8039026B1 (en) | 1997-07-28 | 2011-10-18 | Johnson & Johnson Consumer Companies, Inc | Methods for treating skin pigmentation |
| US8093293B2 (en) | 1998-07-06 | 2012-01-10 | Johnson & Johnson Consumer Companies, Inc. | Methods for treating skin conditions |
| US8106094B2 (en) | 1998-07-06 | 2012-01-31 | Johnson & Johnson Consumer Companies, Inc. | Compositions and methods for treating skin conditions |
| US7985404B1 (en) | 1999-07-27 | 2011-07-26 | Johnson & Johnson Consumer Companies, Inc. | Reducing hair growth, hair follicle and hair shaft size and hair pigmentation |
| US7192615B2 (en) | 2001-02-28 | 2007-03-20 | J&J Consumer Companies, Inc. | Compositions containing legume products |
| JP2002284625A (en) * | 2001-03-23 | 2002-10-03 | Nippon Hypox Lab Inc | Cosmetics |
| FR2848846B1 (en) * | 2002-12-18 | 2005-01-28 | Oreal | COSMETIC USE OF ASCORBIC ACID DERIVATIVES AS BLANCHING AGENTS |
| JP2006052186A (en) * | 2004-08-16 | 2006-02-23 | Toagosei Co Ltd | New dihydroferulic acid condensate |
-
1996
- 1996-09-20 DE DE1996138534 patent/DE19638534A1/en not_active Withdrawn
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1997
- 1997-09-19 JP JP27193497A patent/JPH10120542A/en active Pending
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| Chemical Abstract, Vol.69, 1968, Ref. 16675j * |
| Derwent Abstracts: Ref. 85-319820/51 zu J6 0222-476-A * |
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| Ref. 02604B/02 zu J5 3134-779 * |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8080583B2 (en) | 2007-07-31 | 2011-12-20 | Elc Management Llc | Emulsion cosmetic compositions containing resveratrol derivatives and linear or branched silicone |
| US8084496B2 (en) | 2007-07-31 | 2011-12-27 | Elc Management Llc | Resveratrol ferulate compounds and compositions |
| 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 |
| US8461200B2 (en) | 2007-07-31 | 2013-06-11 | Elc Management Llc | Salicylic acid esters of resveratrol and cosmetic compositions |
| 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 |
| US9220669B2 (en) | 2007-09-08 | 2015-12-29 | Elc Management Llc | Resveratrol ferulate compounds, compositions containing the compounds, and methods of using the same |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH10120542A (en) | 1998-05-12 |
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