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US 4,366,189 AGranted
4-Heterocyclyl-4'-vinylstilbenes
AssigneeCiba-Geigy Corporation
InventorsKurt Burdeska, Guglielmo Kabas, Kurt Weber
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AssigneeCiba-Geigy Corporation
InventorsKurt Burdeska, Guglielmo Kabas, Kurt Weber
Estimating the term…
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.
A 4-heterocyclyl-4'-stilbene of the formula ##STR197## wherein Q is a monocyclic 5- or 6-membered aromatic heterocyclic ring containing nitrogen or containing nitrogen and oxygen, which is unsubstituted or substituted by non-chromophoric groups and which contains 0, 1 or 2 fused benzene rings, or is a bicyclic 9-membered aromatic heterocylic ring, phenyl which is unsubstituted or substituted by non-chromophoric groups, or is cyano, carboxyl, alkoxycarbonyl, alkylsulfonyl or arylsulfonyl, R.sub.0 is hydrogen, or alkyl which is unsubstituted or substituted by non-chromophoric groups, R.sub.1 is hydrogen, or is alkyl, alkoxycarbonyl, carbamoyl or sulfonamide, each of which is unsubstituted or substituted by non-chromophoric groups, or is alkenyl, carboxyl, alkylsulfonyl, arylsulfonyl, aralkylsulfonyl, cyano, sulfo or phosphonic acid dialkyl ester, and R.sub.2 is hydrogen, or is 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.
A process for the production of 4-heterocyclyl-4'-vinylstilbene of the formula ##STR212## wherein Q is a monocyclic 5- or 6-membered aromatic heterocyclic ring, containing nitrogen or containing nitrogen and oxygen, which is unsubstituted or substituted by non-chromophoric groups and which contains 0, 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, alkylsulfonyl or aryl sulfonyl, R.sub.0 is hydrogen, or alkyl which is unsubstituted or substituted by non-chromophoric groups, R.sub.1 is hydrogen, or is alkyl, alkoxycarbonyl, carbamoyl or sulfonamide, each of which is unsubstituted or substituted by non-chromophoric groups, or is alkenyl, carboxyl, alkylsulfonyl, arylsulfonyl, aralkylsulfonyl, cyano, sulfo or phosphonic acid dialkyl ester, and R.sub.2 is hydrogen, or is 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, which process comprises condensing, in the presence of an organic solvent and of a basic condensation agent, a compound of the formula ##STR213## with a compound of the formula ##STR214## in which formulae, Q, R.sub.0, R.sub.1 and R.sub.2 are as defined above and one of Z.sub.1 and Z.sub.2 is the OHC group and the other is a grouping of the formula ##STR215## wherein D.sub.1 is an unsubstituted or a substituted alkyl, aryl, cycloalkyl or aralkyl radical.
Dependencies are inferred from the claim text.