Aniline azo dyes from 1,2,3,4-tetrahydroquinoline and 2,3-dihydro-1,4-benzoxazine couplers containing sulfate alkyl groups

Claim 1

The dye of the formula: ##STR20## wherein ring A is unsubstituted or substituted with 1-3 groups selected from alkyl, alkoxy, chloro, bromo, iodo, trifluoromethyl, thiocyano, cyano, phenylazo, alkanoyl, aroyl, carbamoyl, sulfamoyl, alkylsulfonyl, alkenylsulfonyl, arylsulfonyl, alkylthio, arylthio, aryloxy, alkoxycarbonyl, arylamido, aryloxycarbonyl, COO-alkylene-X, CONH-alkylene-X, ##STR21## SO 2 NH-alkylene-X, ##STR22## SO 2 -alkylene-X, SO 2 N(alkyl) 2 , ##STR23## SO 2 O-aryl, formyl, and NHSO 2 -alkyl, wherein X is one or more groups selected from hydrogen, hydroxy, halogen, aryl, cycloalkyl, alkoxy, aryloxy, alkanoylamino, cyano, alkoxyalkoxy, alkanoyloxy, succinimido, alkylsulfonamido, 2-pyrrolidino, alkylthio and arylthio; and wherein the coupler C has the formula: ##STR24## wherein R 1 is selected from hydrogen, alkyl, alkoxy, halogen, alkanoylamino, alkylthio, and aryloxy; R 3 , R 4 and R 5 are each selected from hydrogen and alkyl; Z is alkylene or --CH 2 (CH 2 ) n X-CH 2 (CH 2 ) p --, where n is 1, 2 or 3, p is 0, 1, 2 or 3, and X is O, S, SO 2 , --SO 2 NH--, --SO 2 N(alkyl)--, SO 2 N(aryl)--, --N(SO 2 aryl)--, --NHCO--, --NHCONH--, --N(SO 2 alkyl)--, or --CON(alkyl)--; M is H + , Na + , K + or NH 4 + ; m is 0, 1 or 2; wherein the alkyl, alkoxy, alkanoyl and aryl substituents of R 1 , R 3 , R 4 , R 5 , and Z are unsubstituted or substituted with up to three of the following groups: aryl, halogen, OSO 3 M, alkoxy, aryloxy, hydroxy, cyclohexyl, furyl, alkylcyclohexyl, aroyloxy, alkoxycarbonyl, alkanoyloxy, sulfamoyl, SO 2 NH(aryl), SO 2 NH(alkyl), SO 2 N(dialkyl), NHCOO(alkyl), NHCONH(alkyl), alkanoylamino, alkylsulfonamido, succinimido, glutarimido, phthalimido, 2-pyrrolidono, cyano, carbamoyl, alkylcarbamoyl, alkoxyalkoxy, alkylthio, arylthio, alkylsulfonyl or arylsulfonyl; wherein each of the alkyl, alkylene and alkenyl portions of the above groups contain 1-6 carbons, and is straight or branched chain.