Ciba-geigy Corporation

Cv I B Ciba-geigy Corporation

Guglielmo Kabas

Geza Kormany

Adolf Emil Siegrist

Hans Schlapfer

Kurt Burdeska

Kurt Weber

Dieter Reinehr

Daniel Bellus

Ian J Fletcher

Alwyn Spencer

Hans-Ulrich Blaser

The invention relates to vinylstilbene compounds of the formula ##STR1## wherein Q is the grouping --COX or ##STR2## These compounds are obtained by reacting 1 molar equivalent of a compound of the formula II ##STR3## wherein X is chlorine, bromine or iodine, in the presence of a base and with the addition of palladium metal or of palladium compounds, as catalyst, which, under the reaction conditions, form labile palladium(O) compounds which do not contain phosphorus, with 1 molar equivalent of a compound of the formula III or with 1 molar equivalent of each of the compounds of the formulae III and IV ##STR4##

Process for the production of vinylstilbene compounds

The invention relates to 4-heterocyclyl-4'-vinylstilbenes of the formula ##STR1## wherein Q is a monocyclic 5- or 6-membered aromatic heterocyclic ring which is unsubstituted or substituted by non-chromophoric groups and which contains no fused benzene rings or 1 or 2 fused benzene rings, or is a bicyclic 9-membered aromatic heterocyclic ring, phenyl which is unsubstituted or substituted by non-chromophoric groups, or is cyano, carboxyl, alkoxycarbonyl or alkylsulfonyl or arylsulfonyl, R.sub.o is hydrogen, alkyl which is unsubstituted or substituted by non-chromophoric groups, R.sub.1 is hydrogen, alkyl, alkoxycarbonyl, carbamoyl or sulfonamide, each of which is unsubstituted or substituted by non-chromophoric groups, or is alkenyl, carboxyl, alkylsulfonyl, arylsulfonyl or aralkylsulfonyl, cyano, sulfo or phosphonic acid dialkyl ester, and R.sub.2 is hydrogen, alkyl or alkenyl, each of which is unsubstituted or substituted by non-chromophoric groups, with the proviso that at most one of R.sub.1 and R.sub.2 is hydrogen. These compounds are used for whitening organic material of high molecular weight, especially polyester. They can be employed in admixture with other fluorescent whitening agents.

4-Heterocyclyl-4'-vinylstilbenes

6-Styrylquinoxalines of the formula ##STR1## in which R and R.sub.1 independently of one another are hydrogen, alkyl, aryl or aryloxy which is unsubstituted or substituted by non-chromophoric substituents, alkoxy, alkoxyalkoxy or phenylthio, R.sub.2 is hydrogen or alkyl and R.sub.3 is cyano or a group of the formula ##STR2## in which R.sub.4 is alkoxy, alkoxyalkoxy, acyloxyalkoxy, ##STR3## These new compounds are suitable for the fluorescent brightening of organic materials of high molecular weight, in particular for brightening polyester textiles and polyester spinning compositions.

6-Styrylquinoxalines, and their use as fluorescent brighteners

Benzoxazolyl-stilbenes of the formula ##STR1## in which R is a 6-membered heterocyclic radical which has 2 nitrogen atoms in the o-position, m-position or p-position relative to one another, and one of Z and Z.sub.o is hydrogen and the other is hydrogen or chlorine, and the benzene nucleus A can carry conventional non-chromophoric substituents, processes for their preparation and their use for the fluorescent brightening of organic material.

Benzoxazolyl-stilbenes

New triazole compounds of formula ##STR1## wherein R.sub.1 represents alkyl of 1 to 6 carbon atoms, R.sub.2 represents alkyl of 1 to 6 carbon atoms or phenyl which is unsubstituted or substituted by halogen, alkyl of 1 to 4 carbon atoms or alkoxy of 1 to 4 carbon atoms, and A represents a radical of certain compounds selected from stylbenes, 2-phenyl-4-styryl-v-triazoles, 3-phenyl-coumarines, 2-phenyl-benzoxazoles, 2-phenyl-benzimidazoles, 2-phenyl-v-triazolo[d]pyrimidine-5,7-diones and 2-biphenyl-v-triazolo[d]pyrimidine-5,7-diones, a process for their preparation as well as a process for optically brightening organic material on using said compounds are disclosed.

Triazole compounds

The invention is directed to new benzoxazole-styryls of the formula ##STR1## wherein the rings A, B, C and D can be substituted, as well as processes for their preparation. The invention relates also to a process for optically brightening high-molecular organic materials on using said compounds.

Benzoxazole-styryls

Stilbene compounds of the formula ##STR1## wherein R denotes the radical ##STR2## and wherein the rings A, B, C, D and E can carry non-chromophoric substituents are useful for the optical brightening of organic materials.

Stilbene compounds

Process for the manufacture of styrene compounds of the formula ##STR1## wherein A denotes one of the ring systems ##STR2## and wherein R.sub.1 denotes hydrogen, alkyl with 1 to 8 carbon atoms, cyclohexyl, phenylalkyl with 1 to 3 carbon atoms in the alkyl part, phenyl, alkoxy with 1 to 4 carbon atoms, or chlorine, or, conjointly with R.sub.2, denotes alkylene with 3 or 4 carbon atoms, R.sub.2 denotes hydrogen or alkyl with 1 to 4 carbon atoms or, conjointly with R.sub.1, denotes alkylene with 3 or 4 carbon atoms, R.sub.3 denotes hydrogen or methyl, R.sub.4 denotes hydrogen, m-methyl, alkyl with 2 to 8 carbon atoms, phenyl, alkoxy with 1 to 4 carbon atoms, or chlorine, or, conjointly with R.sub.5, denotes a fused benzene ring, R.sub.5 denotes hydrogen or chlorine or, conjointly with R.sub.4, denotes a fused benzene ring, X.sub.1 denotes hydrogen, alkyl with 2 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms or chlorine, X.sub.2 denotes hydrogen or chlorine, Y denotes hydrogen, chlorine, alkyl with 1 to 4 carbon atoms or phenyl and Z denotes hydrogen or chlorine, which is characterized in that a methyl compound of the formula ##STR3## is reacted with a Schiff's base of the formula ##STR4## wherein Ar denotes an aromatic radical, in dimethylformamide in the presence of a strongly basic alkali metal compound, the reaction mixture being irradiated, at least initially, with UV light.

Process for the manufacturing of styrene derivatives, new styrene

Styrene compounds of the formula ##STR1## wherein Q denotes one of the ring systems of the formulae ##STR2## wherein M represents oxygen or sulphur, Z represents hydrogen, lower alkyl or phenyl and n represents the number 1 or 2 and the rings A and B can each contain 1 to 3 non-chromophoric substituents.

Styrene compounds

Stilbene compounds of the formula ##STR1## wherein Q denotes the 1,3,4-oxadiazol-2,5-ylene or 1,2,4-oxadiazol-3,5-ylene radical and Q.sub.1 denotes one of the radicals ##STR2## and the rings A, B, C, D and E can each contain 1 to 3 non-chromophoric substituents.

Growing community of inventors

Aesch, Switzerland

Guglielmo Kabas