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AssigneeBayer Aktiengesellschaft
InventorsThomas Scholl, Otto Exner, Peter Finkel, Hermann Perrey
Estimating the term…
An indoline derivative of the formula (I) ##STR1## in which R.sup.1 denotes H or C.sub.1 -C.sub.8 -alkyl; R.sup.2 and R.sup.3 are identical or different and denote C.sub.1 -C.sub.8 -alkyl; R.sup.4 -R.sup.9 are identical or different and denote H, C.sub.1 -C.sub.8 -alkyl, C.sub.5 -C.sub.6 -cycloalkyl or phenyl-C.sub.1 -C.sub.4 -alkyl, or R.sup.5 and R.sup.6 connected together to form a further C.sub.5 -C.sub.6 ring, and R.sup.10 denotes H or one or more radicals selected from the group consisting of C.sub.1 -C.sub.8 -alkyl, C.sub.1 -C.sub.8 alkoxy, C.sub.5 -C.sub.6 -cycloalkyl, phenyl-C.sub.1 -C.sub.4 -alkyl and carb-C.sub.1 -C.sub.8 -alkoxy radicals, or halogen atoms. Such indoline derivative is useful as a UV absorber.
An indoline derivative of the formula (I) ##STR21## in which R.sup.1 denotes H or C.sub.1 -C.sub.8 -alkyl;
N-(dicarboethoxyvinyl)-1,2,3,4-tetrahydroquinoline.
Dependencies are inferred from the claim text.
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Having five membered rings, e.g. pyrrolidone carboxylic acid: having condensed rings, e.g. indol
Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g.…
Indoles; Hydrogenated indoles: with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms…
With only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to the ring carbon atoms: having only hydrogen…
Term ended 21 May 2006 (estimated)
USPTO file history isn’t available for this patent, so only indexed dates are shown.
The present invention relates to new indoline derivatives which are suitable as UV absorbers, and to compositions which contain these UV absorbers to protect the skin from UV radiation.
The sun's radiation comprises, inter alia, the range of ultraviolet radiation which can be divided up into various ranges in respect of the action on the human skin:
(a) UV radiation of the wavelength range 285-320 nm (UVB range) causes sunburn (erythema) on people with normal skins, and this is followed by pigmentation based on photoinduced melanogenesis (indirect pigmentation).
Examples of compounds according to the invention are:
TABLE 1 ______________________________________ .lambda..sub.max E ______________________________________ ##STR6## 330 nm (32.196) 2 ##STR7## 330 nm (30.025) 3 ##STR8## 338 nm 4 ##STR9## 331 nm (26.233) 5 ##STR10## 332 nm (25.310) 6 ##STR11## 317 nm (26.680) ______________________________________
The UVA absorbers according to the invention can be prepared by processes known per se, for example by reaction of malonic esters (VI) with orthocarboxylic esters (V), such as trimethyl orthoformate, triethyl orthoformate, trimethyl orthoacetate, triethyl orthoacetate, triethyl orthopropionate etc., according to scheme A: ##STR12## to give the corresponding alkoxyalkylenemalonic esters (VII), followed by condensation, according to scheme B, with NH-heterocycles (VIII), such as indoline, 2-methylindoline, 2,3,3-trimethyl-5-methoxyindoline, 1,2,3,4,10,11-hexahydrocarbazole, 1,2,3,4-tetrahydroquinoline and 1,2,3,4-tetrahydroquinaldine.