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Novel Indanone Compounds

a technology of indanylidene and compounds, which is applied in the field of new indanylidene compounds, can solve the problems of too low photostability for application

Inactive Publication Date: 2007-08-09
SYMRISE GMBH & CO KG
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

The novel indanylidene compounds exhibit significantly higher photostability and improved compatibility with other UV filters, providing enhanced protection against UV radiation and improving the stability of UV absorbers in various applications, including cosmetics and technical products.

Problems solved by technology

However, the indanylidene compounds previously described in EP-A 823 418 have a photostability which is too low for the application.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

example 1

2-(5,6-Dimethoxy-3,3-dimethyl-1-indanylidene)-4,4-dimethyl-3-oxo-pentanonitrile

[0196]

44 g (0.2 mol) of 5,6-dimethoxy-3,3-dimethyl-1-indanone, 25 g (0.2 mol) of pivaloylacetonitrile, 32 g of propionic acid and 17 g of ammonium acetate are mixed in 80 g of xylene and heated at 120° C. for 7 hours. After the system has been cooled to room temperature and the organic phase has been washed, the xylene is distilled off, and the crude product which remains is recrystallized in methanol. Yield: 50% theory; E1 / 1 730 (λmax 373 nm).

example 2

2-(5-Methoxy-3,3,4,6-tetramethyl-1-indanylidene)-4,4-dimethyl-3-oxo-pentanonitrile

[0197]

[0198] The procedure was analogous to that in Example 1 starting from 5-methoxy-3,3,4,6-tetramethyl-1-indanone. Yield: 50% of theory; E1 / 1 588 (λmax 340 nm).

example 3

2-(3,3,5,6-tetramethyl-1-indanylidene-4,4-dimethyl-3-oxo-pentanonitrile

[0199]

[0200] The procedure was analogous to that in Example 1 starting from 3,3,5,6-tetramethyl-1-indanone. Yield: 55% of theory; E1 / 1 630 (λmax 342 nm).

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Abstract

Novel indanylidene compounds can be used as UV-A filters in cosmetic compositions for protecting skin and hair and for technical applications.

Description

FIELD OF THE INVENTION [0001] The invention relates to novel indanylidene compounds, to a process for their preparation and to their use as UVA filters. BACKGROUND OF THE INVENTION [0002] Indanylidene compounds which have UV-absorbing properties are already known from EP-A 823 418. However, the indanylidene compounds previously described in EP-A 823 418 have a photostability which is too low for the application. SUMMARY OF THE INVENTION [0003] Novel indanylidene compounds of the formula in which [0004] R1 to R4, independently of one another are hydrogen, C1-C20 alkyl or C5-C10-cycloalkyl, with the proviso that two substituents on adjacent carbon atoms can together also be an optionally substituted C1-C4-alkylene group; [0005] may also, independently of one another, be C2-C20-alkyl, in which at least one methylene group may be replaced by oxygen, C3-C20-alkenyl, C3-C20-alkinyl or a group S, [0006] where S may be a silane, an oligosiloxane or a polysiloxane group; [0007] R5 to R8, i...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): A61K31/695A61K31/22A61K31/12C07F7/04C07C49/395A61K8/00A61K8/29A61K8/30A61K8/37A61K8/40A61K8/46A61K8/49A61K8/58A61Q5/00A61Q17/04A61Q19/08C07C255/40C07D319/14C07D319/18C07F7/08C09K3/00G03C1/815
CPCA61K8/40A61K8/498A61K8/585A61Q17/04C07F7/0854C07C2101/14C07C2102/08C07D319/14C07C255/40C07C2601/14C07C2602/08C07F7/0838
Inventor KOCH, OSKARDILK, ERICKLANGNER, ROLANDJOHNCOCK, WILLIAM
Owner SYMRISE GMBH & CO KG
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