DE19755650A1 - Cosmetic and pharmaceutical preparations containing photostable UV filters - Google Patents
Cosmetic and pharmaceutical preparations containing photostable UV filtersInfo
- Publication number
- DE19755650A1 DE19755650A1 DE19755650A DE19755650A DE19755650A1 DE 19755650 A1 DE19755650 A1 DE 19755650A1 DE 19755650 A DE19755650 A DE 19755650A DE 19755650 A DE19755650 A DE 19755650A DE 19755650 A1 DE19755650 A1 DE 19755650A1
- Authority
- DE
- Germany
- Prior art keywords
- compounds
- formula
- cosmetic
- pharmaceutical preparations
- filters
- 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- Withdrawn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
- 239000002537 cosmetic Substances 0.000 title claims description 28
- 239000000825 pharmaceutical preparation Substances 0.000 title claims description 17
- 239000004904 UV filter Substances 0.000 title claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 46
- 239000000203 mixture Substances 0.000 claims description 12
- 239000004611 light stabiliser Substances 0.000 claims description 11
- 125000001424 substituent group Chemical group 0.000 claims description 11
- 238000002360 preparation method Methods 0.000 claims description 10
- 210000003491 skin Anatomy 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 150000007942 carboxylates Chemical group 0.000 claims description 4
- 238000009472 formulation Methods 0.000 claims description 4
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical group [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 4
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 3
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical class CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 claims description 3
- 239000003814 drug Substances 0.000 claims description 3
- 210000002615 epidermis Anatomy 0.000 claims description 3
- 125000001072 heteroaryl group Chemical group 0.000 claims description 3
- 229940127557 pharmaceutical product Drugs 0.000 claims description 3
- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000003282 alkyl amino group Chemical group 0.000 claims description 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 2
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- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 3
- 239000012963 UV stabilizer Substances 0.000 claims 1
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- -1 ammonium radicals Chemical group 0.000 description 77
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- 239000003921 oil Substances 0.000 description 17
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- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- ZAKOWWREFLAJOT-UHFFFAOYSA-N d-alpha-Tocopheryl acetate Natural products CC(=O)OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C ZAKOWWREFLAJOT-UHFFFAOYSA-N 0.000 description 6
- FOYKKGHVWRFIBD-UHFFFAOYSA-N gamma-tocopherol acetate Natural products CC(=O)OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1 FOYKKGHVWRFIBD-UHFFFAOYSA-N 0.000 description 6
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- 239000003205 fragrance Substances 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 5
- 235000019341 magnesium sulphate Nutrition 0.000 description 5
- 150000003254 radicals Chemical class 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 239000011787 zinc oxide Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 239000003109 Disodium ethylene diamine tetraacetate Substances 0.000 description 4
- ZGTMUACCHSMWAC-UHFFFAOYSA-L EDTA disodium salt (anhydrous) Chemical compound [Na+].[Na+].OC(=O)CN(CC([O-])=O)CCN(CC(O)=O)CC([O-])=O ZGTMUACCHSMWAC-UHFFFAOYSA-L 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 239000006071 cream Substances 0.000 description 4
- 235000014113 dietary fatty acids Nutrition 0.000 description 4
- 229940008099 dimethicone Drugs 0.000 description 4
- 239000004205 dimethyl polysiloxane Substances 0.000 description 4
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 4
- 235000019301 disodium ethylene diamine tetraacetate Nutrition 0.000 description 4
- 239000000975 dye Substances 0.000 description 4
- 239000000194 fatty acid Substances 0.000 description 4
- 229930195729 fatty acid Natural products 0.000 description 4
- 150000004665 fatty acids Chemical class 0.000 description 4
- ZCTXEAQXZGPWFG-UHFFFAOYSA-N imidurea Chemical compound O=C1NC(=O)N(CO)C1NC(=O)NCNC(=O)NC1C(=O)NC(=O)N1CO ZCTXEAQXZGPWFG-UHFFFAOYSA-N 0.000 description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- 239000006210 lotion Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 description 4
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 4
- 229960002216 methylparaben Drugs 0.000 description 4
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 239000008177 pharmaceutical agent Substances 0.000 description 4
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- 239000004405 propyl p-hydroxybenzoate Substances 0.000 description 4
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 4
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- LADGBHLMCUINGV-UHFFFAOYSA-N tricaprin Chemical compound CCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCC)COC(=O)CCCCCCCCC LADGBHLMCUINGV-UHFFFAOYSA-N 0.000 description 4
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- 150000002148 esters Chemical class 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
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Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q1/00—Make-up preparations; Body powders; Preparations for removing make-up
- A61Q1/02—Preparations containing skin colorants, e.g. pigments
- A61Q1/04—Preparations containing skin colorants, e.g. pigments for lips
-
- 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
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
-
- 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
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
- A61K2800/52—Stabilizers
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Dermatology (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Cosmetics (AREA)
Description
Die Erfindung betrifft die Verwendung von substituierten α-Me thyl-Styrolderivaten als photostabile UV-Filter in kosmetischen und pharmazeutischen Zubereitungen zum Schutz der menschlichen Epidermis oder menschlicher Haare gegen UV-Strahlung, speziell im Bereich von 320 bis 400 nm.The invention relates to the use of substituted α-Me ethyl styrene derivatives as photostable UV filters in cosmetics and pharmaceutical preparations for the protection of human Epidermis or human hair against UV radiation, especially in the Range from 320 to 400 nm.
Die in kosmetischen und pharmazeutischen Zubereitungen eingesetz ten Lichtschutzmittel haben die Aufgabe, schädigende Einflüsse des Sonnenlichts auf die menschliche Haut zu verhindern oder zu mindest in ihren Auswirkungen zu reduzieren. Daneben dienen diese Lichtschutzmittel aber auch dem Schutz weiterer Inhaltsstoffe vor Zerstörung oder Abbau durch UV-Strahlung. In haarkosmetischen Formulierungen soll eine Schädigung der Keratinfaser durch UV-Strahlen vermindert werden.Used in cosmetic and pharmaceutical preparations th light stabilizers have the task of damaging influences to prevent or prevent sunlight from reaching human skin at least to reduce their effects. In addition, these serve Light stabilizers but also the protection of other ingredients Destruction or degradation by UV radiation. In hair cosmetic Formulations are said to cause damage to the keratin fiber UV rays are reduced.
Das an die Erdoberfläche gelangende Sonnenlicht hat einen Anteil an UV-B- (280 bis 320 nm) und an UV-A-Strahlung (< 320 nm), wel che sich direkt an den Bereich des sichtbaren Lichtes an schließen. Der Einfluß auf die menschliche Haut macht sich besonders bei der UV-B-Strahlung durch Sonnenbrand bemerkbar. Dementspre chend bietet die Industrie eine größere Zahl von Substanzen an, welche die UV-B-Strahlung absorbieren und damit den Sonnenbrand verhindern.The sunlight reaching the surface of the earth has a share to UV-B (280 to 320 nm) and UV-A radiation (<320 nm), wel approach directly to the area of visible light conclude. The influence on human skin is special Noticeable in UV-B radiation through sunburn. Dementspre Accordingly, the industry offers a larger number of substances which absorb UV-B radiation and thus sunburn impede.
Nun haben dermatologische Untersuchungen gezeigt, daß auch die UV-A-Strahlung durchaus Hautschädigungen und Allergien her vorrufen kann, indem beispielsweise das Keratin oder Elastin ge schädigt wird. Hierdurch werden Elastizität und wasserspeicher vermögen der Haut reduziert, d. h. die Haut wird weniger geschmei dig und neigt zur Faltenbildung. Die auffallend hohe Hautkrebs häufigkeit in Gegenden starker Sonneneinstrahlung zeigt, daß of fenbar auch Schädigungen der Erbinformationen in den Zellen durch Sonnenlicht, speziell durch UV-A-Strahlung, hervorgerufen werden. All diese Erkenntnisse lassen daher die Entwicklung effizienter Filtersubstanzen für den UV-A-Bereich notwendig erscheinen.Now dermatological studies have shown that too UV-A radiation can cause skin damage and allergies can cause, for example, the keratin or elastin ge is damaged. This creates elasticity and water storage reduced capacity of the skin, d. H. the skin is less melted dig and tends to wrinkle. The strikingly high level of skin cancer frequency in areas of strong sunlight shows that of Damage to the genetic information in the cells can also be detected Sunlight, especially caused by UV-A radiation. All these findings therefore make development more efficient Filter substances appear necessary for the UV-A range.
Es besteht ein wachsender Bedarf an Lichtschutzmitteln für kosme tische und pharmazeutische Zubereitungen, die vor allem als UV-A-Fil ter dienen können und deren Absorptionsmaxima deshalb im Be reich von ca. 320 bis 380 nm liegen sollten. Um mit einer mög lichst geringen Einsatzmenge die gewünschte Wirkung zu erzielen, sollten derartige Lichtschutzmittel zusätzlich eine hoch spezifi sche Extinktion aufweisen. Außerdem müssen Lichtschutzmittel für kosmetische Präparate noch eine Vielzahl weiterer Anforderungen erfüllen, beispielsweise gute Löslichkeit in kosmetischen Ölen, hohe Stabilität der mit ihnen hergestellten Emulsionen, toxikolo gische Unbedenklichkeit sowie geringen Eigengeruch und geringe Eigenfärbung.There is a growing need for sunscreens for kosme table and pharmaceutical preparations, mainly as UV-A-Fil ter can serve and their absorption maxima therefore in the Be should range from approx. 320 to 380 nm. To be able to to achieve the desired effect in the smallest possible amount, such light stabilizers should also have a highly specifi have cal extinction. In addition, light stabilizers must be used for cosmetic preparations have a variety of other requirements meet, for example good solubility in cosmetic oils, high stability of the emulsions made with them, toxicolo gical harmlessness as well as low inherent odor and low Inherent color.
Eine weitere Anforderung, der Lichtschutzmittel genügen müssen, ist eine ausreichende Photostabilität. Dies ist aber mit den bis her verfügbaren UV-A absorbierenden Lichtschutzmitteln nicht oder nur unzureichend gewährleistet.Another requirement that light stabilizers must meet is is sufficient photostability. But this is with the up not available from UV-A absorbing sunscreens or insufficiently guaranteed.
In der französischen Patentschrift Nr. 2 440 933 wird das 4-(1,1-Dimethylethyl)-4'-methoxydibenzoylmethan als UV-A-Filter beschrieben. Es wird vorgeschlagen, diesen speziellen UV-A-Fil ter, der von der Firma GIVAUDAN unter der Bezeichnung "PARSOL 1789" verkauft wird, mit verschiedenen UV-B-Filtern zu kombi nieren, um die gesamten UV-Strahlen mit einer Wellenlänge von 280 bis 380 nm zu absorbieren.In French patent specification No. 2 440 933 this is 4- (1,1-Dimethylethyl) -4'-methoxydibenzoylmethane as a UV-A filter described. It is suggested to use this special UV-A-Fil ter, sold by GIVAUDAN under the name "PARSOL 1789 "is sold to be combined with various UV-B filters kidneys to absorb the total UV rays with a wavelength of 280 absorb up to 380 nm.
Dieser UV-A-Filter ist jedoch, wenn er allein oder in Kombina tion mit UV-B-Filtern verwendet wird, photochemisch nicht bestän dig genug, um einen anhaltenden Schutz der Haut während eines längeren Sonnenbades zu gewährleisten, was wiederholte Anwendun gen in regelmäßigen und kurzen Abständen erfordert, wenn man ei nen wirksamen Schutz der Haut gegen die gesamten UV-Strahlen er zielen möchte.This UV-A filter is, however, when used alone or in combination tion is used with UV-B filters, not photochemically resistant dig enough to provide lasting skin protection during one to ensure prolonged sunbathing, resulting in repeated applications gen at regular and short intervals when using ei effective protection of the skin against all UV rays want to aim.
Deshalb sollen gemäß EP-A-0 514 491 die nicht ausreichend photo stabilen UV-A-Filter durch den Zusatz von 2-Cyan-3,3-diphenyl acrylsäureestern stabilisiert werden, die selbst im UV-B-Bereich als Filter dienen.Therefore, according to EP-A-0 514 491, the insufficient photo stable UV-A filter through the addition of 2-cyano-3,3-diphenyl Acrylic acid esters are stabilized, even in the UV-B range serve as a filter.
Weiterhin wurde gemäß EP-A-0 251 398 schon vorgeschlagen, UV-A- und UV-B-Strahlung absorbierende Chromophore durch ein Bindeglied in einem Molekül zu vereinen. Dies hat den Nachteil, daß einer seits keine freie Kombination von UV-A- und UV-B-Filtern in der kosmetischen Zubereitung mehr möglich ist und daß Schwierigkeiten bei der chemischen Verknüpfung der Chromophore nur bestimmte Kom binationen zulassen.Furthermore, it has already been proposed according to EP-A-0 251 398, UV-A and Chromophores absorbing UV-B radiation through a link to unite in one molecule. This has the disadvantage that one on the other hand, there is no free combination of UV-A and UV-B filters in the cosmetic preparation is more possible and that difficulties in the chemical linkage of the chromophores only certain com allow binations.
In der deutschen Patentschrift Nr. 1087 902 wird die Verwendung von Kondensationsprodukten aus Oxy- bzw. Alkoxybenzaldehyden und CH-aciden Verbindungen als UV-Filter in technischen Anwendungen, beispielsweise in Kunststoffen beschrieben. In the German patent specification No. 1087 902, the use of condensation products from oxy- or alkoxybenzaldehydes and CH-acidic compounds as UV filters in technical applications, described for example in plastics.
DE 28 16 819 beschreibt 4-Methoxybenzylidencyanessigester als UV-A-Filter in der kosmetischen Anwendung, wobei die in dieser Pa tentschrift offenbarten Verbindungen nur eine unzureichende Pho tostabilität aufweisen. Ein weiterer Nachteil ist, daß bei der Synthese der hier beschriebenen UV-Absorber cis/trans-Gemische anfallen, die, wenn sie als solches eingesetzt werden, ein unein heitliches Gemisch mit unterschiedlichen Absorptionseigenschaften bilden. Für die Verwendung der reinen Isomeren ist eine aufwen dige Aufreinigung erforderlich.DE 28 16 819 describes 4-Methoxybenzylidenidenessigester as UV-A filters in cosmetic use, with those in this Pa Tentschrift disclosed compounds only an insufficient Pho have stability. Another disadvantage is that the Synthesis of the UV absorber cis / trans mixtures described here incurred, which, when used as such, are a disagreement Uniform mixture with different absorption properties form. For the use of the pure isomers is an expense thorough purification required.
Es bestand daher die Aufgabe, Lichtschutzmittel für kosmetische und pharmazeutische Zwecke vorzuschlagen, die im UV-A-Bereich mit hoher Extinktion absorbieren, die photostabil sind, eine geringe Eigenfarbe d. h. eine scharfe Bandenstruktur aufweisen und je nach Substituent in Öl oder Wasser löslich sind.The object was therefore to find light stabilizers for cosmetic and to propose pharmaceutical purposes that are in the UV-A range absorb high absorbance, which are photostable, a low one Own color d. H. have a sharp band structure and depending on Substituent are soluble in oil or water.
Diese Aufgabe wurde erfindungsgemäß gelöst durch Verwendung von
substituierten α-Methyl-Styrolderivaten der Formel I
According to the invention, this object was achieved by using substituted α-methyl-styrene derivatives of the formula I.
in der die Variablen folgende Bedeutung haben:
R1 C4-C10-Alkoxy, C1-C12-Alkylamino, C1-C12-Dialkylamino, wasser
löslich machende Substituenten, ausgewählt aus der Gruppe be
stehend aus Carboxylat-, Sulfonat- oder Ammoniumresten;
R2 Wasserstoff, C2-C10-Alkyl, C1-C12-Alkoxy;
R3 COOR5, COR5, CONR5R6, CN;
R4 COOR5, COR5, CONR5R6, CN;
wobei die Substituenten R3 und R4 jeweils gleich sind;
R5 und R6 unabhängig voneinander Wasserstoff, C1-C12-Alkyl, C2-C10-Alke
nyl, C3-C10-Cycloalkyl, C3-C10-Cycloalkenyl, Aryl, Heteroaryl,
gegebenenfalls substituiert;
als photostabile UV-Filter in kosmetischen und pharmazeutischen
Zubereitungen zum Schutz der menschlichen Haut oder menschlicher
Haare gegen Sonnenstrahlen, allein oder zusammen mit an sich für
kosmetische und pharmazeutische Zubereitungen bekannten, im
UV-Bereich absorbierenden Verbindungen.in which the variables have the following meaning:
R 1 C 4 -C 10 alkoxy, C 1 -C 12 alkylamino, C 1 -C 12 dialkylamino, water-solubilizing substituents selected from the group consisting of carboxylate, sulfonate or ammonium radicals;
R 2 is hydrogen, C 2 -C 10 -alkyl, C 1 -C 12 -alkoxy;
R 3 COOR 5 , COR 5 , CONR 5 R 6 , CN;
R 4 COOR 5 , COR 5 , CONR 5 R 6 , CN;
where the substituents R 3 and R 4 are each the same;
R 5 and R 6 independently of one another are hydrogen, C 1 -C 12 alkyl, C 2 -C 10 alkenyl, C 3 -C 10 cycloalkyl, C 3 -C 10 cycloalkenyl, aryl, heteroaryl, optionally substituted;
as photostable UV filters in cosmetic and pharmaceutical preparations for protecting the human skin or human hair against sun rays, alone or together with compounds which are known per se for cosmetic and pharmaceutical preparations and absorb in the UV range.
Als Alkylreste für R2 seien verzweigte oder unverzweigte C2-C10-Alkylketten, bevorzugt Ethyl, n-Propyl, 1-Methylethyl, n-Butyl, 1-Methylpropyl-, 2-Methylpropyl, 1,1-Dimethylethyl, n-Pen tyl, 1-Methylbutyl, 2-Methylbutyl, 3-Methylbutyl, 2,2-Dimethyl propyl, 1-Ethylpropyl, n-Hexyl, 1,1-Dimethylpropyl, 1,2-Dimethyl propyl, 1-Methylpentyl, 2-Methylpentyl, 3-Methylpentyl, 4-Methyl pentyl, 1,1-Dimethylbutyl, 1,2-Dimethylbutyl, 1,3-Dimethylbutyl, 2,2-Dimethylbutyl, 2,3-Dimethylbutyl, 3,3-Dimethylbutyl, 1-Ethyl butyl, 2-Ethylbutyl, 1,1,2-Trimethylpropyl, 1,2,2-Trimethylpro pyl, 1-Ethyl-1-methylpropyl, 1-Ethyl-2-methylpropyl, n-Heptyl, n-Octyl, n-Nonyl, n-Decyl genannt.As alkyl radicals for R 2 are branched or unbranched C 2 -C 10 -alkyl chains, preferably ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl-, 2-methylpropyl, 1,1-dimethylethyl, n-pen tyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methyl pentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethyl butyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl, 1-ethyl-2-methylpropyl, n-heptyl, n-octyl, n-nonyl, n -Decyl called.
Als Alkylreste für R5 und R6 seien verzweigte oder unverzweigte C1-C12-Alkylketten, bevorzugt Methyl, Ethyl, n-Propyl, 1-Methyl ethyl, n-Butyl, 1-Methylpropyl-, 2-Methylpropyl, 1,1-Dimethyl ethyl, n-Pentyl, 1-Methylbutyl, 2-Methylbutyl, 3-Methylbutyl, 2,2-Dimethylpropyl, 1-Ethylpropyl, n-Hexyl, 1,1-Dimethylpropyl, 1,2-Dimethylpropyl, 1-Methylpentyl, 2-Methylpentyl, 3-Methyl pentyl, 4-Methylpentyl, 1,1-Dimethylbutyl, 1,2-Dimethylbutyl, 1,3-Dimethylbutyl, 2,2-Dimethylbutyl, 2,3-Dimethylbutyl, 3,3-Dimethylbutyl, 1-Ethylbutyl, 2-Ethylbutyl, 1,1,2-Trimethyl propyl, 1,2,2-Trimethylpropyl, 1-Ethyl-1-methylpropyl, 1-Ethyl-2-methylpropyl, n-Heptyl, n-Octyl, n-Nonyl, n-Decyl, n-Undecyl, n-Dodecyl genannt.As alkyl radicals for R 5 and R 6 , branched or unbranched C 1 -C 12 -alkyl chains, preferably methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl, 1,1 -Dimethyl ethyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methyl pentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1 -Ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl, 1-ethyl-2-methylpropyl, n-heptyl, n-octyl, n- Nonyl, n-decyl, n-undecyl, n-dodecyl called.
Als Alkenylreste R5 und R6 seien verzweigte oder unverzweigte C2-C10-Alkenylketten, bevorzugt Vinyl, Propenyl, Isopropenyl, 1-Butenyl, 2-Butenyl, 1-Pentenyl, 2-Pentenyl, 2-Methyl-1-butenyl, 2-Methyl-2-butenyl, 3-Methyl-1-butenyl, 1-Hexenyl, 2-Hexenyl, 1-Heptenyl, 2-Heptenyl, 1-Octenyl oder 2-Octenyl genannt.Alkenyl radicals R 5 and R 6 are branched or unbranched C 2 -C 10 alkenyl chains, preferably vinyl, propenyl, isopropenyl, 1-butenyl, 2-butenyl, 1-pentenyl, 2-pentenyl, 2-methyl-1-butenyl, 2-methyl-2-butenyl, 3-methyl-1-butenyl, 1-hexenyl, 2-hexenyl, 1-heptenyl, 2-heptenyl, 1-octenyl or 2-octenyl.
Als Cycloalkylreste seien für R5 und R6 bevorzugt verzweigte oder unverzweigte C3-C10-Cycloalkylketten wie Cyclopropyl, Cyclobutyl, Cyclopentyl, Cyclohexyl, Cycloheptyl, 1-Methylcyclopropyl, 1-Ethylcyclopropyl, 1-Propylcyclopropyl, 1-Butylcyclopropyl, 1-Pentylcyclopropyl, 1-Methyl-1-Butylcyclopropyl, 1,2-Dimethylcy clypropyl, 1-Methyl-2-Ethylcyclopropyl, Cyclooctyl, Cyclononyl oder Cyclodecyl genannt.Preferred cycloalkyl radicals for R 5 and R 6 are branched or unbranched C 3 -C 10 cycloalkyl chains such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, 1-methylcyclopropyl, 1-ethylcyclopropyl, 1-propylcyclopropyl, 1-butylcyclopropyl, 1-butylcyclopropyl, , 1-methyl-1-butylcyclopropyl, 1,2-dimethylcyclypropyl, 1-methyl-2-ethylcyclopropyl, cyclooctyl, cyclononyl or cyclodecyl called.
Als Cycloalkenylreste seien für R5 und R6 bevorzugt verzweigte oder unverzweigte, C3-C10-Cycloalkenylketten mit einer oder mehre ren Doppelbindungen wie Cyclopropenyl, Cyclobutenyl, Cyclopente nyl, Cyclopentadienyl, Cyclohexenyl, 1,3-Cyclohexadienyl, 1,4-Cyclohexadienyl, Cycloheptenyl, Cycloheptatrienyl, Cycloocte nyl, 1,5-Cyclooctadienyl, Cyclooctatetraenyl, Cyclononenyl oder Cyclodecyl genannt.Preferred cycloalkenyl radicals for R 5 and R 6 are branched or unbranched, C 3 -C 10 cycloalkenyl chains with one or more double bonds such as cyclopropenyl, cyclobutenyl, cyclopentene nyl, cyclopentadienyl, cyclohexenyl, 1,3-cyclohexadienyl, 1,4-cyclohexadienyl , Cycloheptenyl, Cycloheptatrienyl, Cycloocte nyl, 1,5-Cyclooctadienyl, Cyclooctatetraenyl, Cyclononenyl or Cyclodecyl called.
Die Cycloalkenyl- und Cycloalkylreste können ggf. mit einem oder mehreren, z. B. 1 bis 3 Resten wie Halogen z. B. Fluor, Chlor oder Brom, Cyano, Nitro, Amino, C1-C4-Alkylamino, C1-C4-Dialkylamino, Hydroxy, C1-C4-Alkyl, C1-C4-Alkoxy oder anderen Resten substi tuiert sein oder 1 bis 3 Heteroatome wie Schwefel, Stickstoff, dessen freie Valenzen durch Wasserstoff oder C1-C4-Alkyl abgesät tigt sein können oder Sauerstoff im Ring enthalten.The cycloalkenyl and cycloalkyl radicals can optionally with one or more, z. B. 1 to 3 radicals such as halogen z. B. fluorine, chlorine or bromine, cyano, nitro, amino, C 1 -C 4 -alkylamino, C 1 -C 4 -dialkylamino, hydroxy, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy or other radicals be substituted or 1 to 3 heteroatoms such as sulfur, nitrogen, the free valences of which can be saturated by hydrogen or C 1 -C 4 -alkyl or contain oxygen in the ring.
Als Alkoxyreste für R1 kommen solche mit 4 bis 10 C-Atomen, vor zugsweise mit 4 bis 8 C-Atomen in Betracht.Suitable alkoxy radicals for R 1 are those with 4 to 10 carbon atoms, preferably with 4 to 8 carbon atoms.
Beispielsweise sind zu nennen:
Examples include:
Als Alkoxyreste für R2 kommen solche mit 1 bis 12 C-Atomen, vor zugsweise mit 1 bis 8 C-Atomen in Betracht.Suitable alkoxy radicals for R 2 are those with 1 to 12 carbon atoms, preferably with 1 to 8 carbon atoms.
Beispielsweise sind zu nennen:
Examples include:
Als Mono- oder Dialkylaminoreste für R1 und R2 kommen solche in Betracht, die Alkylreste mit 1 bis 12 C-Atomen enthalten, wie z. B. Methyl-, n-Propyl-, n-Butyl-, 2-Methylpropyl-, 1,1-Dimethyl propyl-, Hexyl-, Heptyl-, 2-Ethylhexyl-, Isopropyl-, 1-Methylpro pyl-, n-Pentyl-, 3-Methylbutyl-, 2,2-Dimethylpropyl-, 1-Methyl-1-ethylpropyl- und Octyl.Suitable mono- or dialkylamino radicals for R 1 and R 2 are those which contain alkyl radicals having 1 to 12 carbon atoms, such as. B. methyl, n-propyl, n-butyl, 2-methylpropyl, 1,1-dimethyl propyl, hexyl, heptyl, 2-ethylhexyl, isopropyl, 1-methylpro pyl, n- Pentyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-methyl-1-ethylpropyl and octyl.
Unter Aryl sind aromatische Ringe oder Ringsysteme mit 6 bis 18 Kohlenstoffatomen im Ringsystem zu verstehen, beispielsweise Phenyl oder Naphthyl, die ggf. mit einem oder mehreren Resten wie Halogen z. B. Fluor, Chlor oder Brom, Cyano, Nitro, Amino, C1-C4- Alkylamino, C1-C4-Dialkylamino, Hydroxy, C1-C4-Alkyl, C1-C4-Alkoxy oder anderen Resten substituiert sein können. Bevorzugt sind ggf. substituiertes Phenyl, Methoxyphenyl und Naphthyl.Aryl is to be understood as meaning aromatic rings or ring systems with 6 to 18 carbon atoms in the ring system, for example phenyl or naphthyl, optionally with one or more radicals such as halogen, for. B. fluorine, chlorine or bromine, cyano, nitro, amino, C 1 -C 4 -alkylamino, C 1 -C 4 -dialkylamino, hydroxy, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy or other radicals can be substituted. Optionally substituted phenyl, methoxyphenyl and naphthyl are preferred.
Heteroaryl-Reste sind vorteilhaft erweise einfache oder konden sierte aromatische Ringsysteme mit einem oder mehreren heteroaro matischen 3- bis 7-gliedrigen Ringen. Als Heteroatome können ein oder mehrere Stickstoff-, Schwefel- und/oder Sauerstoffatome im Ring oder Ringsystem enthalten sein.Heteroaryl radicals are advantageously simple or condensed based aromatic ring systems with one or more heteroaro matic 3- to 7-membered rings. As heteroatoms can be a or more nitrogen, sulfur and / or oxygen atoms in the Ring or ring system be included.
Hydrophile d. h. die Wasserlöslichkeit der Verbindungen der Formel I ermöglichende Reste für R1 und R2 sind z. B. Carboxy- und Sulf oxyreste und insbesondere deren Salze mit beliebigen physiolo gisch verträglichen Kationen, wie die Alkalisalze oder wie die Trialkylammoniumsalze, wie Tri-(hydroxyalkyl)-ammoniumsalze oder die 2-Methylpropan-1-ol-2-ammoniumsalze. Ferner kommen Ammonium reste, insbesondere Alkylammoniumreste mit beliebigen physiolo gisch verträglichen Anionen in Betracht.Hydrophilic ie the water solubility of the compounds of formula I enabling radicals for R 1 and R 2 are z. B. carboxy and sulf oxy radicals and especially their salts with any physiologically compatible cations, such as the alkali metal salts or the trialkylammonium salts, such as tri (hydroxyalkyl) ammonium salts or the 2-methylpropan-1-ol-2-ammonium salts. Ammonium residues, in particular alkylammonium residues with any physiologically compatible anions, are also suitable.
Bevorzugt sind solche Verbindungen der Formel I, in der
R1 C4-C6-Alkoxy, insbesondere 3-Methylbutoxy, n-Butoxy und
n-Hexoxy,
wasserlöslich machende Substituenten, ausgewählt aus der
Gruppe bestehend aus Carboxylat-, Sulfonat- oder Ammoniumre
sten;
R2 Wasserstoff, C2-C4-Alkyl, Ethyl, n-Propyl, iso-Propyl,
C1-C8-Alkoxy, insbesondere Methoxy;
R3 CN
R4 CN;
bedeutet.Those compounds of the formula I are preferred in which
R 1 C 4 -C 6 alkoxy, in particular 3-methylbutoxy, n-butoxy and n-hexoxy,
water-solubilizing substituents selected from the group consisting of carboxylate, sulfonate or ammonium radicals;
R 2 is hydrogen, C 2 -C 4 -alkyl, ethyl, n-propyl, iso-propyl, C 1 -C 8 -alkoxy, in particular methoxy;
R 3 CN
R 4 CN;
means.
Die Substituenten R1 und R2 können jeweils in ortho, meta oder para Position am Aromaten gebunden sein. Besonders bevorzugt sind Verbindungen der Formel I, in denen R1 in der para- und R2 in der meta-Position vorliegen.The substituents R 1 and R 2 can each be bonded to the aromatic in the ortho, meta or para position. Compounds of the formula I in which R 1 is in the para and R 2 in the meta position are particularly preferred.
Weiterhin weisen Verbindungen der Formel I besondere photostabile Eigenschaften aus, bei denen die Substituenten R1 bis R4 in der in Tabelle 1 genannten Kombination vorliegen: Furthermore, compounds of the formula I have particular photostable properties in which the substituents R 1 to R 4 are present in the combination specified in Table 1:
Aus US 3 275 50 sind bereits Verbindungen der allgemeinen Formel
11 bekannt.
Compounds of the general formula 11 are already known from US Pat. No. 3,275,50.
Hinsichtlich des von UV-A-Absorbern geforderten Eigenschaftspro fils, wie u. a. eine gute Öllöslichkeit, eine UV-Stabilität < 95% sowie eine hohe spezifische Extinktion konnten nur die erfin dungsgemäßen Verbindungen der allgemeinen Formel I diese Bedin gungen erfüllen.With regard to the properties required by UV-A absorbers fils, such as good oil solubility, UV stability <95% as well as a high specific absorbance could only be achieved by the inventor according to compounds of the general formula I this condition meet requirements.
Gegenüber dem Stand der Technik weisen die erfindungsgemäßen
α-Methyl-Styrolderivate der Formel I folgende Vorteile auf:
Compared to the prior art, the α-methyl-styrene derivatives of the formula I according to the invention have the following advantages:
Öllöslichkeit: < 10%
E1 1: 723
Photostabilität: < 95%
Oil solubility: <10%
E 1 1 : 723
Photo stability: <95%
Öllöslichkeit: < 10%
E1 1: 678
Photostabilität: < 95%.Oil solubility: <10%
E 1 1 : 678
Photo stability: <95%.
Öllöslichkeit: < 10%
E1 1: 950
Photostabilität: 80%
Oil solubility: <10%
E 1 1 : 950
Photo stability: 80%
Öllöslichkeit: < 2%
E1 1: 800
Photostabilität: < 95%
Oil solubility: <2%
E 1 1 : 800
Photo stability: <95%
Öllöslichkeit: < 5%
E1 1: 550
Photostabilität: < 95%
Oil solubility: <5%
E 1 1 : 550
Photo stability: <95%
Öllöslichkeit: < 10%
E1 1: 400
Photostabilität: < 95%.Oil solubility: <10%
E 1 1 : 400
Photo stability: <95%.
α-Methyl statt α-Phenyl: bessere Öllöslichkeit,
höhere Extinktion
α-Methyl statt α-Wasserstoff: bessere Photostabilität
(R1 α-methyl instead of α-phenyl: better oil solubility, higher extinction
α-methyl instead of α-hydrogen: better photostability
(R 1
): OC4 ): OC 4
H9 H 9
statt OCH3 instead of OCH 3
: bessere Öllöslichkeit
(R1 : better oil solubility
(R 1
): OC4 ): OC 4
H9 H 9
statt OC12 instead of OC 12
H25 H 25
: höhere Extinktion.: higher absorbance.
Die erfindungsgemäß zu verwendenden Verbindungen der Formel I
können nach der Gleichung
The compounds of the formula I to be used according to the invention can be prepared according to the equation
durch Kondensation hergestellt werden, wobei R1 bis R4 die im Anspruch 1 genannte Bedeutung haben.be prepared by condensation, where R 1 to R 4 have the meaning given in claim 1.
Beispielsweise ergibt die Umsetzung von 4-(3'-Methylbutoxy)-ace tophenon mit Malonsäuredinitril die Verbindung 1 in Tab. 2.For example, the reaction of 4- (3'-methylbutoxy) ace gives tophenon with malononitrile gives compound 1 in Tab. 2.
Gegenstand der vorliegenden Erfindung sind weiterhin kosmetische und pharmazeutische Zubereitungen, die 0,1 bis 10 Gew.-%, vor zugsweise 1 bis 7 Gew.-%, bezogen auf die gesamte Menge der kos metischen und pharmazeutischen Zubereitung, eine oder mehrere der Verbindungen der Formel I zusammen mit an sich für kosmetische und pharmazeutische Zubereitungen bekannten, im UV-B-Bereich ab sorbierenden Verbindungen als Lichtschutzmittel enthalten, wobei die Verbindungen der Formel I in der Regel in geringerer Menge als die UV-B-absorbierenden Verbindungen eingesetzt werden. The present invention also relates to cosmetic products and pharmaceutical preparations containing 0.1 to 10% by weight preferably 1 to 7 wt .-%, based on the total amount of kos metallic and pharmaceutical preparation, one or more of the Compounds of the formula I together with per se for cosmetic and pharmaceutical preparations known in the UV-B range Sorbent compounds contain as light stabilizers, wherein the compounds of the formula I usually in a smaller amount can be used as the UV-B absorbing compounds.
Der größte Teil der Lichtschutzmittel in den zum Schutz der menschlichen Epidermis dienenden kosmetischen und pharmazeuti schen Zubereitungen besteht aus Verbindungen, die UV-Licht im UV-B-Bereich absorbieren d. h. im Bereich von 280 bis 320 nm. Bei spielsweise beträgt der Anteil der erfindungsgemäß zu verwenden den UV-A-Absorber 10 bis 90 Gew.-%, bevorzugt 20 bis 50 Gew.-% bezogen auf die Gesamtmenge von UV-B und UV-A absorbierenden Sub stanzen.Most of the sunscreens in the to protect the Cosmetic and pharmaceutical products used for human epidermis preparations consists of compounds that absorb UV light Absorb UV-B range d. H. in the range from 280 to 320 nm. At for example, the proportion is to be used according to the invention the UV-A absorber 10 to 90% by weight, preferably 20 to 50% by weight based on the total amount of UV-B and UV-A absorbing sub punch.
Die Lichtschutzmittel enthaltenden kosmetischen und pharmazeuti schen Zubereitungen sind in der Regel auf der Basis eines Trä gers, der mindestens eine Ölphase enthält. Es sind aber auch Zubereitungen allein auf wäßriger Basis bei Verwendung von Ver bindungen mit hydrophilen Substituenten möglich. Demgemäß kommen Öle, Öl-in-Wasser- und Wasser-in-Öl-Emulsionen, Cremes und Pa sten, Lippenschutzstiftmassen oder fettfreie Gele in Betracht.The cosmetic and pharmaceutical products containing light stabilizers cal preparations are usually based on a Trä gers, which contains at least one oil phase. But there are too Preparations on a water basis only when using Ver bonds with hydrophilic substituents possible. Come accordingly Oils, oil-in-water and water-in-oil emulsions, creams and pa sten, lip protection stick masses or fat-free gels into consideration.
Solche Sonnenschutzpräparate können demgemäß in flüssiger, pastö ser oder fester Form vorliegen, beispielsweise als Wasser-in-Öl-Cremes, Öl-in-Wasser-Cremes und -Lotionen, Aerosol-Schaumcremes, Gele, Öle, Fettstifte, Puder, Sprays oder alkoholisch-wäßrige Lotionen.Such sunscreen preparations can accordingly be liquid, pasty in water or solid form, for example as water-in-oil creams, Oil-in-water creams and lotions, aerosol foam creams, Gels, oils, grease pencils, powders, sprays or alcoholic-watery ones Lotions.
Übliche Ölkomponenten in der Kosmetik sind beispielsweise Paraf finöl, Glycerylstearat, Isopropylmyristat, Diisopropyladipat, 2-Ethylhexansäurecetylstearylester, hydriertes Polyisobuten, Va seline, Caprylsäure/Caprinsäure-Triglyceride, mikrokristallines Wachs, Lanolin und Stearinsäure.Common oil components in cosmetics are, for example, paraf fin oil, glyceryl stearate, isopropyl myristate, diisopropyl adipate, Cetylstearyl 2-ethylhexanoate, hydrogenated polyisobutene, Va seline, caprylic acid / capric acid triglycerides, microcrystalline Wax, lanolin and stearic acid.
Übliche kosmetische Hilfsstoffe, die als Zusätze in Betracht kom men können, sind z. B. Co-Emulgatoren, Fette und Wachse, Stabili satoren, Verdickungsmittel, biogene Wirkstoffe, Filmbildner, Duftstoffe, Farbstoffe, Perlglanzmittel, Konservierungsmittel, Pigmente, Elektrolyte (z. B. Magnesiumsulfat) und pH-Regulatoren. Als Co-Emulgatoren kommen vorzugsweise bekannte W/O- und daneben auch O/W-Emulgatoren wie etwa Polyglycerinester, Sorbitanester oder teilveresterte Glyceride in Betracht. Typische Beispiele für Fette sind Glyceride; als Wachse sind u. a. Bienenwachs, Paraffin wachs oder Mikrowachse gegebenenfalls in Kombination mit hydro philen Wachsen zu nennen. Als Stabilisatoren können Metallsalze von Fettsäuren wie z. B. Magnesium-, Aluminium- und/oder Zinkstea rat eingesetzt werden. Geeignete Verdickungsmittel sind bei spielsweise vernetzte Polyacrylsäuren und deren Derivate, Poly saccharide, insbesondere Xanthan-Gum, Guar-Guar, Agar-Agar, Algi nate und Tylosen, Carboxymethylcellulose und Hydroxyethylcellu lose, ferner Fettalkohole, Monoglyceride und Fettsäuren, Polycry late, Polyvinylalkohol und Polyvinylpyrrolidon. Unter biogenen Wirkstoffen sind beispielsweise Pflanzenextrakte, Eiweißhydroly sate und Vitaminkomplexe zu verstehen. Gebräuchliche Filmbildner sind beispielsweise Hydrocolloide wie Chitosan, mikrokristallines Chitosan oder quaterniertes Chitosan, Polyvinylpyrrolidon, Vinyl pyrrolodon-Vinylacetat-Copolymerisate, Polymere der Acrylsäure reihe, quaternäre Cellulose-Derivate und ähnliche Verbindungen. Als Konservierungsmittel eignen sich beispielsweise Formaldehyd lösung, p-Hydroxybenzoat oder Sorbinsäure. Als Perlglanzmittel kommen beispielsweise Glycoldistearinsäureester wie Ethylengly coldistearat, aber auch Fettsäuren und Fettsäuremonoglycolester in Betracht. Als Farbstoffe können die für kosmetische Zwecke geeigneten und zugelassenen Substanzen verwendet werden, wie sie beispielsweise in der Publikation "Kosmetische Färbemittel" der Farbstoffkoimmission der Deutschen Forschungsgemeinschaft, veröf fentlicht im Verlag Chemie, Weinheim, 1984, zusammengestellt sind. Diese Farbstoffe werden üblicherweise in Konzentration von 0,001 bis 0,1 Gew.-%, bezogen auf die gesamte Mischung, einge setzt.Usual cosmetic auxiliaries that can be used as additives men are z. B. co-emulsifiers, fats and waxes, stabilizers agents, thickeners, biogenic agents, film formers, Fragrances, dyes, pearlescent agents, preservatives, Pigments, electrolytes (e.g. magnesium sulfate) and pH regulators. Known W / O and in addition are preferably used as co-emulsifiers also O / W emulsifiers such as polyglycerol esters, sorbitan esters or partially esterified glycerides. Typical examples of Fats are glycerides; as waxes are inter alia. Beeswax, paraffin wax or micro waxes, optionally in combination with hydro phile waxes. Metal salts can be used as stabilizers of fatty acids such as B. magnesium, aluminum and / or zinc stea council are used. Suitable thickeners are at for example crosslinked polyacrylic acids and their derivatives, poly saccharides, in particular xanthan gum, guar guar, agar agar, algi nate and tylose, carboxymethyl cellulose and hydroxyethyl cellulose loose, also fatty alcohols, monoglycerides and fatty acids, polycry late, polyvinyl alcohol and polyvinyl pyrrolidone. Under biogenic Active ingredients are, for example, plant extracts, protein hydrolytes To understand sate and vitamin complexes. Common film formers are for example hydrocolloids such as chitosan, microcrystalline Chitosan or quaternized chitosan, polyvinylpyrrolidone, vinyl pyrrolodone-vinyl acetate copolymers, polymers of acrylic acid series, quaternary cellulose derivatives and similar compounds. Formaldehyde, for example, is suitable as a preservative solution, p-hydroxybenzoate or sorbic acid. As a pearlescent agent for example glycol distearic acid esters such as ethylene glycol cold distearate, but also fatty acids and fatty acid monoglycol esters into consideration. As dyes, those for cosmetic purposes can be used Appropriate and approved substances are used as they are for example in the publication "Cosmetic colorants" Dye Coordination of the German Research Foundation, publ published by Verlag Chemie, Weinheim, 1984, compiled are. These dyes are usually used in concentrations of 0.001 to 0.1 wt .-%, based on the total mixture, incorporated puts.
Der Gesamtanteil der Hilfs- und Zusatzstoffe kann 1 bis 80, vor zugsweise 6 bis 40 Gew.-% und der nicht wäßrige Anteil ("Aktiv substanz") 20 bis 80, vorzugsweise 30 bis 70 Gew.-% - bezogen auf die Mittel - betragen. Die Herstellung der Mittel kann in an sich bekannter Weise, d. h. beispielsweise durch Heiß-, Kalt-, Heiß- Heiß/Kalt- bzw. PIT-Emulgierung erfolgen. Hierbei handelt es sich um ein rein mechanisches Verfahren, eine chemische Reaktion fin det nicht statt.The total amount of auxiliaries and additives can be 1 to 80, before preferably 6 to 40% by weight and the non-aqueous portion ("Aktiv substance ") 20 to 80, preferably 30 to 70 wt .-% - based on the means - amount. The preparation of the means can in itself known way, d. H. for example by hot, cold, hot Hot / cold or PIT emulsification take place. This is it a purely mechanical process, a chemical reaction fin det does not take place.
Schließlich können weitere an sich bekannte im UV-A-Bereich ab sorbierenden Substanzen mitverwendet werden, sofern sie im Ge samtsystem der erfindungsgemäß zu verwendenden Kombination aus UV-B und UV-A Filter stabil sind.Finally, others known per se in the UV-A range can be used Sorbing substances are also used, provided they are in the Ge complete system of the combination to be used according to the invention UV-B and UV-A filters are stable.
Als UV-Filtersubstanzen, die in Kombination mit den erfindungsge
mäß zu verwendenden Verbindungen der Formel I angewandt werden,
kommen beliebige UV-A- und UV-B-Filtersubstanzen in Betracht.
Beispielsweise sind zu nennen:
Any UV-A and UV-B filter substances can be used as UV filter substances which are used in combination with the compounds of the formula I to be used according to the invention. Examples include:
Schließlich sind auch mikronisierte Pigmente wie Titandioxid und Zinkoxid zu nennen. Finally, micronized pigments such as titanium dioxide and To mention zinc oxide.
Zum Schutz menschlicher Haare vor UV-Strahlen können die erfin dungsgemäßen Lichtschutzmittel der Formel I in Shampoos, Lotio nen, Gelen, Haarsprays, Aerosol-Schaumcremes oder Emulsionen in Konzentrationen von 0,1 bis 10 Gew.-%, bevorzugt 1 bis 7 Gew.-% eingearbeitet werden. Die jeweiligen Formulierungen können dabei u. a. zum Waschen, Färben sowie zum Frisieren der Haare verwendet werden.To protect human hair from UV rays, the inventions can appropriate light stabilizers of the formula I in shampoos, lotions ns, gels, hairsprays, aerosol foam creams or emulsions in Concentrations from 0.1 to 10% by weight, preferably 1 to 7% by weight be incorporated. The respective formulations can thereby i.a. used for washing, coloring and styling hair will.
Die erfindungsgemäß zu verwendenden Verbindungen zeichnen sich in der Regel durch ein besonders hohes Absorptionsvermögen im Bereich der UV-A-Strahlung mit scharfer Bandenstruktur aus. Wei terhin sind sie gut in kosmetischen Ölen löslich und lassen sich leicht in kosmetische Formulierungen einarbeiten. Die mit den Verbindungen I hergestellten Emulsionen zeichnen sich besonders durch ihre hohe Stabilität, die Verbindungen I selber durch ihre hohe Photostabilität aus, und die mit I hergestellten Zubereitun gen durch ihr angenehmes Hautgefühl aus.The compounds to be used according to the invention are distinguished usually due to a particularly high absorption capacity in the UV-A radiation with a sharp band structure. White Furthermore, they are readily soluble in cosmetic oils and can be easily incorporated into cosmetic formulations. The ones with the Compounds I produced emulsions stand out particularly due to their high stability, the connections I themselves due to their high photostability, and the preparations made with I through their pleasant feeling on the skin.
Die UV-Filterwirkung der erfindungsgemäßen Verbindungen der For mel I kann auch zur Stabilisierung von Wirk- und Hilfsstoffen in kosmetischen und pharmazeutischen Formulierungen ausgenutzt wer den.The UV filter effect of the compounds according to the invention of For mel I can also be used to stabilize active ingredients and auxiliaries in cosmetic and pharmaceutical formulations who exploited the.
Gegenstand der Erfindung sind auch die Verbindungen der Formel I zur Verwendung als Medikament sowie pharmazeutische Mittel zur vorbeugenden Behandlung von Entzündungen und Allergien der Haut sowie zur Verhütung bestimmter Hautkrebsarten, welche eine wirk same Menge mindestens einer Verbindung der Formel I als Wirkstoff enthalten.The invention also relates to the compounds of the formula I for use as medicaments and pharmaceutical agents for preventive treatment of inflammation and allergies of the skin as well as for the prevention of certain types of skin cancers, which have an effective same amount of at least one compound of formula I as active ingredient contain.
Das erfindungsgemäße pharmazeutische Mittel kann oral oder to pisch verabreicht werden. Für die orale Verabreichung liegt das pharmazeutische Mittel in Form von u. a. Pastillen, Gelatinekap seln, Dragees, als Sirup, Lösung, Emulsion oder Suspension vor. Die topische Anwendung der pharmazeutischen Mittel erfolgt bei spielsweise als Salbe, Creme, Gel, Spray, Lösung oder Lotion. The pharmaceutical agent according to the invention can be oral or to administered pisch. For oral administration that is pharmaceutical agents in the form of i.a. Lozenges, gelatine caps sugar, coated tablets, as a syrup, solution, emulsion or suspension. The topical application of the pharmaceutical agent takes place at for example as an ointment, cream, gel, spray, solution or lotion.
0,1 mol 4-(3'-Methylbutoxy)-acetophenon und 0,1 mol Malonsäuredi
nitril wurden in 100 ml Toluol gelöst, auf Rückfluß erhitzt und
mit 20 ml einer Mischung aus Ammoniumacetat und Eisessig tropfen
weise versetzt. Das entstehende Reaktionswasser wurde azeotrop
entfernt. Nach dem Abkühlen wurde mit Wasser gewaschen, die orga
nische Phase mit Natriumsulfat getrocknet und im Vakuum einge
engt. Der Rückstand wurde aus Methanol/Wasser kristallisiert.
0.1 mol of 4- (3'-methylbutoxy) acetophenone and 0.1 mol of Malonsäuredi nitrile were dissolved in 100 ml of toluene, heated to reflux and treated dropwise with 20 ml of a mixture of ammonium acetate and glacial acetic acid. The resulting water of reaction was removed azeotropically. After cooling, it was washed with water, and the organic phase was dried with sodium sulfate and concentrated in vacuo. The residue was crystallized from methanol / water.
Ausbeute: 7.9 g (33% d. Th.). Reinheit: < 99% (GC).Yield: 7.9 g (33% of theory). Purity: <99% (GC).
Die Herstellung der Verbindungen 2 bis 4 der Tabelle 2 erfolgt analog Beispiel 1.Compounds 2 to 4 of Table 2 are prepared analogous to example 1.
Eine 5 Gew.-%ige alkoholische Lösung des zu prüfenden Licht schutzmittels wird mittels einer Eppendorfpipette (20 µl) auf die Auffräsung eines Glasplättchens aufgetragen. Durch die Anwesen heit des Alkohols verteilt sich die Lösung gleichmäßig auf der aufgerauten Glasoberfläche. Die aufgetragene Menge entspricht der Menge an Lichtschutzmittel, die in Sonnencremes zur Erreichung eines mittleren Lichtschutzfaktors benötigt wird. Bei der Prüfung werden jeweils 4 Glasplättchen bestrahlt. Die Abdampfzeit und die Bestrahlung betragen je 30 Minuten. Die Glasplättchen werden wäh rend des Bestrahlens durch eine Wasserkühlung, die sich am Boden des Suntestgeräte befindet, leicht gekühlt. Die Temperatur inner halb des Suntest Gerätes beträgt während der Bestrahlung 40°C. Nachdem die Proben bestrahlt worden sind, werden sie mit Ethanol in einen dunklen 50 ml Meßkolben gewaschen und mit dem Photometer vermessen. Die Blindproben werden ebenso auf Glasplättchen aufge tragen und 30 Minuten bei Raumtemperatur abgedampft. Wie die an deren Proben werden sie mit Ethanol abgewaschen und auf 100 ml verdünnt und vermessen. A 5% strength by weight alcoholic solution of the light to be tested protective agent is applied to the Milling of a glass plate applied. Through the estate The solution is evenly distributed over the alcohol roughened glass surface. The applied amount corresponds to Amount of sunscreen used in sunscreens to achieve a medium sun protection factor is required. During the exam 4 glass plates are irradiated in each case. The evaporation time and the Irradiation is 30 minutes each. The glass slides are weh rend of irradiation through a water cooling system, which is located on the ground of the sun test device is slightly cooled. The temperature inside half of the Suntest device is 40 ° C during irradiation. After the samples have been irradiated, they are washed with ethanol Washed in a dark 50 ml volumetric flask and measured with the photometer measured. The blank samples are also placed on glass slides wear and evaporated for 30 minutes at room temperature. Like that on their samples are washed off with ethanol and made up to 100 ml diluted and measured.
Photostabilität: < 95%
Photo stability: <95%
Photostabilität: 72%
Photo stability: 72%
Photostabilität: 81%
Photo stability: 81%
Photostabilität: 78%
Photo stability: 78%
Photostabilität: 81%
Photo stability: 81%
Photostabilität: 80%.Photostability: 80%.
Alle öllöslichen Bestandteile werden in einem Rührkessel auf 85°C erwärmt. Wenn alle Bestandteile geschmolzen sind, bzw. als Flüssigphase vorliegen, wird die Wasserphase unter Homogenisieren eingearbeitet. Unter Rühren wird die Emulsion auf ca. 40°C abge kühlt, parfümiert, homogenisiert und dann unter ständigem Rühren auf 25°C abgekühlt. All oil-soluble components are in a stirred tank Heated to 85 ° C. When all components are melted or as If the liquid phase is present, the water phase is homogenized incorporated. The emulsion is removed to approx. 40 ° C. with stirring cools, perfumes, homogenizes and then with constant stirring cooled to 25 ° C.
ad 100 Eucerinum anhydricum
10,00 Glycerin
10,00 Titanium Dioxid
5,00 Verbindung Nr. 1 der Tabelle 2
8,00 Octyl Methoxycinnamat
5,00 Zink Oxid
4,00 Castoröl
4,00 Pentaerythrithil Stearat/caprat/Caprylat Adipat
3,00 Glyceryl Stearat SE
2,00 Bienenwachs
2,00 Microkristallines Wachs
2,00 Quaternium-18 Bentonit
1,50 PEG-45/Dodecyl Glycol Copolymer.ad 100 Eucerinum anhydricum
10.00 glycerin
10.00 titanium dioxide
5.00 Compound No. 1 of Table 2
8.00 octyl methoxycinnamate
5.00 zinc oxide
4.00 castor oil
4.00 Pentaerythrithil stearate / caprate / caprylate adipate
3.00 glyceryl stearate SE
2.00 beeswax
2.00 microcrystalline wax
2.00 Quaternium-18 bentonite
1.50 PEG-45 / dodecyl glycol copolymer.
ad 100 Eucerinum anhydricum
10,00 Glycerin
10,00 Titanium Dioxid
5,00 Verbindung Nr. 2 der Tabelle 2
8,00 Octyl Methoxycinnamat
5,00 Zink Oxid
4,00 Castoröl
4,00 Pentaerythrithil Stearat/caprat/Caprylat Adipat
3,00 Glyceryl Stearat SE
2,00 Bienenwachs
2,00 Microkristallines Wachs
2,00 Quaternium-18 Bentonit
1,50 PEG-45/Dodecyl Glycol Copolymer. ad 100 Eucerinum anhydricum
10.00 glycerin
10.00 titanium dioxide
5.00 Compound No. 2 of Table 2
8.00 octyl methoxycinnamate
5.00 zinc oxide
4.00 castor oil
4.00 Pentaerythrithil stearate / caprate / caprylate adipate
3.00 glyceryl stearate SE
2.00 beeswax
2.00 microcrystalline wax
2.00 Quaternium-18 bentonite
1.50 PEG-45 / dodecyl glycol copolymer.
ad 100 Wasser
10,00 Octyl Methoxcinnamat
6,00 PEG-7-Hydrogenated Castor Öl
6,00 Titanium Dioxid
5,00 Verbindung Nr. 1 der Tabelle 2
5,00 Mineral Öl
5,00 Isoamyl p-Methoxycinnamat
5,00 Propylen Glycol
3,00 Jojoba Öl
3,00 4-Methylbenzyliden Campher
2,00 PEG-45/Dodecyl Glycol Copolymer
1,00 Dimethicon
0,50 PEG-40-Hydrogenated Castor Öl
0,50 Tocopheryl Acetat
0,50 Phenoxyethanol
0,20 EDTA.ad 100 water
10.00 octyl methoxycinnamate
6.00 PEG-7 Hydrogenated Castor Oil
6.00 titanium dioxide
5.00 Compound No. 1 of Table 2
5.00 mineral oil
5.00 isoamyl p-methoxycinnamate
5.00 propylene glycol
3.00 jojoba oil
3.00 4-methylbenzylidene camphor
2.00 PEG-45 / dodecyl glycol copolymer
1.00 dimethicone
0.50 PEG-40 Hydrogenated Castor Oil
0.50 tocopheryl acetate
0.50 phenoxyethanol
0.20 EDTA.
ad 100 Wasser
10,00 Octyl Methoxcinnamat
6,00 PEG-7-Hydrogenated Castor Öl
6,00 Titanium Dioxid
5,00 Verbindung Nr. 2 der Tabelle 2
5,00 Mineral Öl
5,00 Isoamyl p-Methoxycinnamat
5,00 Propylen Glycol
3,00 Jojoba Öl
3,00 4-Methylbenzyliden Campher
2,00 PEG-45/Dodecyl Glycol Copolymer
1,00 Dimethicon
0,50 PEG-40-Hydrogenated Castor Öl
0,50 Tocopheryl Acetat
0,50 Phenoxyethanol
0,20 EDTA. ad 100 water
10.00 octyl methoxycinnamate
6.00 PEG-7 Hydrogenated Castor Oil
6.00 titanium dioxide
5.00 Compound No. 2 of Table 2
5.00 mineral oil
5.00 isoamyl p-methoxycinnamate
5.00 propylene glycol
3.00 jojoba oil
3.00 4-methylbenzylidene camphor
2.00 PEG-45 / dodecyl glycol copolymer
1.00 dimethicone
0.50 PEG-40 Hydrogenated Castor Oil
0.50 tocopheryl acetate
0.50 phenoxyethanol
0.20 EDTA.
ad 100 Wasser
8,00 Octyl Methoxycinnamat
7,00 Titanium Dioxid
5,00 Verbindung Nr. 1 der Tabelle 2
5,00 Glycerin
5,00 PEG-25 PABA
1,00 4-Methylbenzyliden Campher
0,40 Acrylate C10-C30 Alkyl Acrylat Crosspolymer
0,30 Imidazolidinyl Urea
0,25 Hydroxyethyl Cellulose
0,25 Sodium Methylparaben
0,20 Disodium EDTA
0,15 Fragrance
0,15 Sodium Propylparaben
0,10 Sodium Hydroxid.ad 100 water
8.00 octyl methoxycinnamate
7.00 titanium dioxide
5.00 Compound No. 1 of Table 2
5.00 glycerin
5.00 PEG-25 PABA
1.00 4-methylbenzylidene camphor
0.40 Acrylate C10-C30 alkyl acrylate cross polymer
0.30 imidazolidinyl urea
0.25 hydroxyethyl cellulose
0.25 sodium methyl paraben
0.20 disodium EDTA
0.15 fragrance
0.15 sodium propyl paraben
0.10 sodium hydroxide.
ad 100 Wasser
8,00 Octyl Methoxycinnamat
7,00 Titanium Dioxid
5,00 Verbindung Nr. 2 der Tabelle 2
5,00 Glycerin
5,00 PEG-25 PABA
1,00 4-Methylbenzyliden Campher
0,40 Acrylate C10-C30 Alkyl Acrylat Crosspolymer
0,30 Imidazolidinyl Urea
0,25 Hydroxyethyl Cellulose
0,25 Sodium Methylparaben
0,20 Disodium EDTA
0,15 Fragrance
0,15 Sodium Propylparaben
0,10 Sodium Hydroxid. ad 100 water
8.00 octyl methoxycinnamate
7.00 titanium dioxide
5.00 Compound No. 2 of Table 2
5.00 glycerin
5.00 PEG-25 PABA
1.00 4-methylbenzylidene camphor
0.40 Acrylate C10-C30 alkyl acrylate cross polymer
0.30 imidazolidinyl urea
0.25 hydroxyethyl cellulose
0.25 sodium methyl paraben
0.20 disodium EDTA
0.15 fragrance
0.15 sodium propyl paraben
0.10 sodium hydroxide.
ad 100 Wasser
8,00 Octyl Methoxycinnamat
8,00 Titanium Dioxid
6,00 PEG-7-Hydrogenated Castor Öl
5,00 Verbindung Nr. 1 der Tabelle 2
6,00 Mineral Öl
5,00 Zink Oxid
5,00 Isopropyl Palmitat
5,00 Imidazolidinyl Urea
3,00 Jojoba Öl
2,00 PEG-45/Dodecyl Glycol Copolymer
1,00 4-Methylbenzyliden Campher
0,60 Magnesium Stearat
0,50 Tocopheryl Acetat
0,25 Methylparaben
0,20 Disodium EDTA
0,15 Propylparaben.ad 100 water
8.00 octyl methoxycinnamate
8.00 titanium dioxide
6.00 PEG-7 Hydrogenated Castor Oil
5.00 Compound No. 1 of Table 2
6.00 mineral oil
5.00 zinc oxide
5.00 isopropyl palmitate
5.00 imidazolidinyl urea
3.00 jojoba oil
2.00 PEG-45 / dodecyl glycol copolymer
1.00 4-methylbenzylidene camphor
0.60 magnesium stearate
0.50 tocopheryl acetate
0.25 methyl paraben
0.20 disodium EDTA
0.15 propyl paraben.
ad 100 Wasser
8,00 Octyl Methoxycinnamat
8,00 Titanium Dioxid
6,00 PEG-7-Hydrogenated Castor Öl
5,00 Verbindung Nr. 2 der Tabelle 2
6,00 Mineral Öl
5,00 Zink Oxid
5,00 Isopropyl Palmitat
5,00 Imidazolidinyl Urea
3,00 Jojoba Öl
2,00 PEG-45/Dodecyl Glycol Copolymer
1,00 4-Methylbenzyliden Campher
0,60 Magnesium Stearat
0,50 Tocopheryl Acetat
0,25 Methylparaben
0,20 Disodium EDTA
0,15 Propylparaben.ad 100 water
8.00 octyl methoxycinnamate
8.00 titanium dioxide
6.00 PEG-7 Hydrogenated Castor Oil
5.00 Compound No. 2 of Table 2
6.00 mineral oil
5.00 zinc oxide
5.00 isopropyl palmitate
5.00 imidazolidinyl urea
3.00 jojoba oil
2.00 PEG-45 / dodecyl glycol copolymer
1.00 4-methylbenzylidene camphor
0.60 magnesium stearate
0.50 tocopheryl acetate
0.25 methyl paraben
0.20 disodium EDTA
0.15 propyl paraben.
ad 100 Wasser
8,00 Octyl Methoxycinnamat
5,00 PEG-7-Hydrogenated Castor Öl
5,00 Propylene Glycol
4,00 Isopropyl Palmitat
4,00 Caprylic/Capric Triglycerid
5,00 Verbindung Nr. 1 der Tabelle 2
4,00 Glycerin
3,00 Jojoba Öl
2,00 4-Methylbenzyliden Campher
2,00 Titanium Dioxid
1,50 PEG-45/Dodecyl Glycol Copolymer
1,50 Dimethicon
0,70 Magnesium Sulfat
0,50 Magnesium Stearat
0,15 Fragrance.ad 100 water
8.00 octyl methoxycinnamate
5.00 PEG-7 Hydrogenated Castor Oil
5.00 Propylene Glycol
4.00 isopropyl palmitate
4.00 Caprylic / Capric Triglyceride
5.00 Compound No. 1 of Table 2
4.00 glycerin
3.00 jojoba oil
2.00 4-methylbenzylidene camphor
2.00 titanium dioxide
1.50 PEG-45 / dodecyl glycol copolymer
1.50 dimethicone
0.70 magnesium sulfate
0.50 magnesium stearate
0.15 fragrance.
ad 100 Wasser
8,00 Octyl Methoxycinnamat
5,00 PEG-7-Hydrogenated Castor Öl
5,00 Propylene Glycol
4,00 Isopropyl Palmitat
4,00 Caprylic/Capric Triglycerid
5,00 Verbindung Nr. 2 der Tabelle 2
4,00 Glycerin
3,00 Jojoba Öl
2,00 4-Methylbenzyliden Campher
2,00 Titanium Dioxid
1,50 PEG-45/Dodecyl Glycol Copolymer
1,50 Dimethicon
0,70 Magnesium Sulfat
0,50 Magnesium Stearat
0,15 Fragrance.ad 100 water
8.00 octyl methoxycinnamate
5.00 PEG-7 Hydrogenated Castor Oil
5.00 Propylene Glycol
4.00 isopropyl palmitate
4.00 Caprylic / Capric Triglyceride
5.00 Compound No. 2 of Table 2
4.00 glycerin
3.00 jojoba oil
2.00 4-methylbenzylidene camphor
2.00 titanium dioxide
1.50 PEG-45 / dodecyl glycol copolymer
1.50 dimethicone
0.70 magnesium sulfate
0.50 magnesium stearate
0.15 fragrance.
ad 100 Wasser
10,00 Mineral Öl
6,00 PEG-7-Hydrogenated Castor Öl
5,00 Isopropyl Palmitat
3,50 Octyl Methoxycinnamat
5,00 Verbindung Nr. 1 der Tabelle 2
3,00 Caprylic/Capric Triglycerid
3,00 Jojoba Öl
2,00 PEG-45/Dodecyl Glycol Copolymer
0,70 Magnesium Sulfat
0,60 Magnesium Stearat
0,50 Tocopheryl Acetat
0,30 Glycerin
0,25 Methylparaben
0,15 Propylparaben
0,05 Tocopherol.ad 100 water
10.00 mineral oil
6.00 PEG-7 Hydrogenated Castor Oil
5.00 isopropyl palmitate
3.50 octyl methoxycinnamate
5.00 Compound No. 1 of Table 2
3.00 Caprylic / Capric Triglyceride
3.00 jojoba oil
2.00 PEG-45 / dodecyl glycol copolymer
0.70 magnesium sulfate
0.60 magnesium stearate
0.50 tocopheryl acetate
0.30 glycerin
0.25 methyl paraben
0.15 propyl paraben
0.05 tocopherol.
ad 100 Wasser
10,00 Mineral Öl
6,00 PEG-7-Hydrogenated Castor Öl
5,00 Isopropyl Palmitat
3,50 Octyl Methoxycinnamat
5,00 Verbindung Nr. 2 der Tabelle 2
3,00 Caprylic/Capric Triglycerid
3,00 Jojoba Öl
2,00 PEG-45/Dodecyl Glycol Copolymer
0,70 Magnesium Sulfat
0,60 Magnesium Stearat
0,50 Tocopheryl Acetat
0,30 Glycerin
0,25 Methylparaben
0,15 Propylparaben
0,05 Tocopherol.ad 100 water
10.00 mineral oil
6.00 PEG-7 Hydrogenated Castor Oil
5.00 isopropyl palmitate
3.50 octyl methoxycinnamate
5.00 Compound No. 2 of Table 2
3.00 Caprylic / Capric Triglyceride
3.00 jojoba oil
2.00 PEG-45 / dodecyl glycol copolymer
0.70 magnesium sulfate
0.60 magnesium stearate
0.50 tocopheryl acetate
0.30 glycerin
0.25 methyl paraben
0.15 propyl paraben
0.05 tocopherol.
Claims (8)
in der die Variablen folgende Bedeutung haben:
R1 C4-C10-Alkoxy, C1-C12-Alkylamino, C1-C12-Dialkylamino, was serlöslich machende Substituenten, ausgewählt aus der Gruppe bestehend aus Carboxylat-, Sulfonat- oder Ammoni umresten;
R2 Wasserstoff, C2-C10-Alkyl, C1-C12-Alkoxy;
R3 COOR5, COR5, CONR5R6, CN;
R4 COOR5, COR5, CONR5R6, CN;
wobei die Substituenten R3 und R4 jeweils gleich sind;
R5 und R6 unabhängig voneinander Wasserstoff, C1-C12-Alkyl, C2-C10-Alkenyl, C3-C10-Cycloalkyl, C3-C10-Cycloalkenyl, Aryl, Heteroaryl, gegebenenfalls substituiert;
als photostabile UV-Filter in kosmetischen und pharmazeuti schen Zubereitungen zum Schutz der menschlichen Haut oder menschlicher Haare gegen Sonnenstrahlen, allein oder zusammen mit an sich für kosmetische und pharmazeutische Zubereitungen bekannten, im UV-Bereich absorbierenden Verbindungen.1. Use of substituted α-methyl styrene derivatives of the formula I,
in which the variables have the following meaning:
R 1 C 4 -C 10 alkoxy, C 1 -C 12 alkylamino, C 1 -C 12 dialkylamino, what solubilizing substituents selected from the group consisting of carboxylate, sulfonate or ammonium radicals;
R 2 is hydrogen, C 2 -C 10 -alkyl, C 1 -C 12 -alkoxy;
R 3 COOR 5 , COR 5 , CONR 5 R 6 , CN;
R 4 COOR 5 , COR 5 , CONR 5 R 6 , CN;
where the substituents R 3 and R 4 are each the same;
R 5 and R 6 independently of one another are hydrogen, C 1 -C 12 -alkyl, C 2 -C 10 -alkenyl, C 3 -C 10 -cycloalkyl, C 3 -C 10 -cycloalkenyl, aryl, heteroaryl, optionally substituted;
as photostable UV filters in cosmetic and pharmaceutical preparations for protecting human skin or human hair against sun rays, alone or together with compounds that are known per se for cosmetic and pharmaceutical preparations and absorb in the UV range.
R1 C4-C6-Alkoxy, wasserlöslich machende Substituenten, aus gewählt aus der Gruppe bestehend aus Carboxylat-, Sulfo nat- oder Ammoniumresten;
R2 Wasserstoff, C2-C4-Alkyl, C1-C4-Alkoxy;
R3 gleich
R4 CN.4. Use of compounds of the formula I according to claims 1 to 3, where the substituents have the following meanings:
R 1 C 4 -C 6 alkoxy, water-solubilizing substituents selected from the group consisting of carboxylate, sulfonate or ammonium radicals;
R 2 is hydrogen, C 2 -C 4 -alkyl, C 1 -C 4 -alkoxy;
R 3 the same
R 4 CN.
enthalten, in der die Variablen die Bedeutung gemäß Anspruch 1 haben.5. Cosmetic and pharmaceutical preparations containing light stabilizers for protecting the human epidermis or human hair against UV light in the range from 280 to 400 nm, characterized in that they are in a cosmetically and pharmaceutically suitable carrier, alone or together with for cosmetic and pharmaceutical preparations known compounds of the formula I which absorb UV rays, effective amounts of compounds of the formula I as photosta bile UV filters
contain, in which the variables have the meaning according to claim 1.
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19755650A DE19755650A1 (en) | 1997-10-20 | 1997-12-15 | Cosmetic and pharmaceutical preparations containing photostable UV filters |
| EP98119094A EP0911020B1 (en) | 1997-10-20 | 1998-10-09 | Methylstyrene derivatives as UV-filters and cosmetic and pharmaceutical preparations containing them |
| ES98119094T ES2217475T3 (en) | 1997-10-20 | 1998-10-09 | METHYL-STYRENE DERIVATIVES AS UV FILTERS AND COSMETIC AND PHARMACEUTICAL PREPARATIONS CONTAINING THESE. |
| DE59810942T DE59810942D1 (en) | 1997-10-20 | 1998-10-09 | Methyl styrene derivatives as UV filters and cosmetic and pharmaceutical preparations containing them |
| US09/172,672 US6090374A (en) | 1997-10-20 | 1998-10-15 | Cosmetic and pharmaceutical preparations comprising photostable UV filters |
| AU89367/98A AU755281B2 (en) | 1997-10-20 | 1998-10-16 | Cosmetic and pharmaceutical preparations comprising photostable UV filters |
| JP29670198A JP4021572B2 (en) | 1997-10-20 | 1998-10-19 | Use of substituted α-methylstyrene derivatives as UV filters, sunscreens and pharmaceutical formulations containing them |
| CN98125008A CN1218661A (en) | 1997-10-20 | 1998-10-20 | Cosmetics and medicine containing light stable ultraviolet filter agent |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19746001 | 1997-10-20 | ||
| DE19755650A DE19755650A1 (en) | 1997-10-20 | 1997-12-15 | Cosmetic and pharmaceutical preparations containing photostable UV filters |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE19755650A1 true DE19755650A1 (en) | 1999-04-22 |
Family
ID=7845893
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19755650A Withdrawn DE19755650A1 (en) | 1997-10-20 | 1997-12-15 | Cosmetic and pharmaceutical preparations containing photostable UV filters |
| DE59810942T Expired - Fee Related DE59810942D1 (en) | 1997-10-20 | 1998-10-09 | Methyl styrene derivatives as UV filters and cosmetic and pharmaceutical preparations containing them |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE59810942T Expired - Fee Related DE59810942D1 (en) | 1997-10-20 | 1998-10-09 | Methyl styrene derivatives as UV filters and cosmetic and pharmaceutical preparations containing them |
Country Status (1)
| Country | Link |
|---|---|
| DE (2) | DE19755650A1 (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2000023044A1 (en) * | 1998-10-16 | 2000-04-27 | The Procter & Gamble Company | Uv protection compositions |
| WO2000065142A1 (en) * | 1999-04-27 | 2000-11-02 | Basf Aktiengesellschaft | Uv-absorbers with an affinity for textile fibres |
| EP1059082A1 (en) * | 1999-06-11 | 2000-12-13 | Basf Aktiengesellschaft | Use of substituted vinyltetrahydronaphthalenes and vinylbenzotetrahydropyrans as sunscreens |
| EP1961453A2 (en) | 2004-05-03 | 2008-08-27 | Symrise GmbH & Co. KG | Benzyliden-ß-dicarbonyl compounds as UV-absorbers |
-
1997
- 1997-12-15 DE DE19755650A patent/DE19755650A1/en not_active Withdrawn
-
1998
- 1998-10-09 DE DE59810942T patent/DE59810942D1/en not_active Expired - Fee Related
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2000023044A1 (en) * | 1998-10-16 | 2000-04-27 | The Procter & Gamble Company | Uv protection compositions |
| US6224854B1 (en) | 1998-10-16 | 2001-05-01 | The Procter & Gamble Company | UV protection compositions |
| WO2000065142A1 (en) * | 1999-04-27 | 2000-11-02 | Basf Aktiengesellschaft | Uv-absorbers with an affinity for textile fibres |
| US6916778B1 (en) | 1999-04-27 | 2005-07-12 | Basf Aktiengesellschaft | UV absorbers with affinity for textile fiber |
| EP1059082A1 (en) * | 1999-06-11 | 2000-12-13 | Basf Aktiengesellschaft | Use of substituted vinyltetrahydronaphthalenes and vinylbenzotetrahydropyrans as sunscreens |
| EP1961453A2 (en) | 2004-05-03 | 2008-08-27 | Symrise GmbH & Co. KG | Benzyliden-ß-dicarbonyl compounds as UV-absorbers |
Also Published As
| Publication number | Publication date |
|---|---|
| DE59810942D1 (en) | 2004-04-15 |
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| Date | Code | Title | Description |
|---|---|---|---|
| 8130 | Withdrawal |