2-Amino-cinnamoylthiophene acid azo dye compounds having an aniline, tetrahydroquinoline, or benzomorpholine coupler

Claim 1

A dye compound having the formula ##STR75## wherein each R 14 is H or alkyl; each R is a substituent independently selected from alkyl, hydroxy, alkoxy, carboxy, halogen, nitro, alkoxycarbonyl, alkanoyloxy, alkanoyl, alkylamino, cyano, dialkylamino, and alkyl substituted with 1-3 of halogen, alkoxy, alkanoyl, alkanoyloxy, alkoxycarbonyl, alkanoylamino, cyano, nitro, carbamoyl, alkylcarbamoyl, sulfamoyl, or alkylsulfamoyl; R 12 and R 13 are each selected from H, alkyl, alkoxy, alkanoyl, halogen, alkylsulfonyl, alkanoyloxy, SO 2 NH 2 , SO 2 NHalkyl, SO 2 N(alkyl) 2 , CONH 2 , CONHalkyl, --COOH, CON(alkyl) 2 , arylsulfonyl, alkanoyl, alkanoylamido, aroyl, aryl, alkylthio, arylthio, alkenylthio, alkoxycarbonyl, hydroxyalkylcarbamoyl, cyclohexylthio, SO 3 C 6 H 5 , cyano, thiocyano, cyclohexylsulfonyl, cyclohexyl, and alkyl substituted with 1-3 of alkoxy, cyano, halogen, SO 2 alkyl, CONHalkyl, alkanoyloxy, or SO 2 NHalkyl; C 1 is an aniline, tetrahydroquinoline, or benzomorpholine type azo type dye coupler which is unsubstituted or substituted; wherein at least one --SO 3 M, or --OSO 3 M group is present in said dye compound where M is selected from H + , NH 4 + , Na + , K + , and the colorless cations of sulfuric acid or sulfonic acid salts of trimethylamine, triethylamine, and N,N-dimethylaniline; and wherein the coupler is selected from ##STR76## wherein: R 1 and R 2 are each selected from hydrogen, fluorine, chlorine, bromine, alkyl, aryl, cycloalkyl, --COOH, alkoxy, phenoxy, alkylthio, arylthio, and radicals having the formula --NH--X--R 9 in which X is --CO--, --COO--, or --SO 2 -- and R 9 is selected from alkyl and alkyl substituted with halogen, hydroxy, phenoxy, aryl, cyano, cycloalkyl, alkylsulfonyl, alkylthio, alkanoyloxy, and alkoxy, and when X is --CO-- in the formula --NH--X--R 9 , R 9 also can be hydrogen, amino, alkenyl, alkylamino, dialkylamino, arylamino, aryl, or furyl; R 3 and R 4 are selected from hydrogen; cycloalkyl; cycloalkyl substituted with one or two groups selected from alkyl, --OH, alkoxy, halogen, --COOH, and hydroxy substituted alkyl; phenyl or phenyl substituted with alkyl, --COOH, alkoxy, halogen, alkanoylamino, cyano or alkoxycarbonyl; straight or branched alkenyl; straight or branched alkyl and such alkyl substituted with 1-3 of the following: hydroxy; --COOH; halogen; cyano; amino; alkoxy; hydroxyalkoxy; succinimido; glutarimido; phenylcarbamoyloxy; phthalimido; phthalimidino; 2-pyrrolidono; cyclohexyl; phenoxy; phenyl or phenyl substituted with alkyl, alkoxy, halogen, alkanoylamino, cyano or alkoxycarbonyl; alkanoylamino; sulfamoyl; alkylsulfamoyl; vinylsulfonyl; acrylamido; benzoylsulfonicimido; alkylsulfonamido; phenylsulfonamido; alkoxycarbonylamino; alkylcarbamoyloxy; alkoxycarbonyl; alkoxycarbonyloxy; alkenylcarbonylamino; a group of the formula ##STR77## wherein Y is ##STR78## wherein R 10 is alkyl, phenyl, phenyl substituted with halogen, alkyl, alkoxy, alkanoylamino, cyano, or alkoxycarbonyl, pyridyl, pyrimidinyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, or ##STR79## --OXR 9 ; --NH--X--R 9 ; --X--R 9 ; --CONR 11 R 11 ; --SO 2 NR 11 R 11 ; wherein R 9 and X are as defined above and each R 11 is selected from H, alkyl, and alkyl substituted with 1-3 of halogen, hydroxy, phenoxy, alkoxy, aryl, cyano, cycloalkyl, alkylsulfonyl, alkylthio, alkanoyl, and alkanoyloxy; alkoxy substituted with hydroxy, cyano, alkanoyloxy, or alkoxy; phenoxy substituted with one or more of alkyl, alkoxy or halogen; and R 3 and R 4 combined as pentamethylene, ethyleneoxyethylene or ethylenesulfonylethylene which, with the nitrogen atom to which it is attached, forms a ring; R 5 , R 6 , R 7 and R 8 are each selected from hydrogen and alkyl; and wherein at least one of R, R 1 , R 2 , R 3 , R 4 , R 12 and R 13 is --SO 3 M or --OSO 3 M, or wherein an alkyl, cycloalkyl or aryl moiety thereof is substituted with 1-3 of --SO 3 M or --OSO 3 M.