Azo dyes from a 2-aminothiophene having 1 or 2 sulfated hydroxyalkoxycarbonyl or N-(hydrocyalkyl) carbamoyl groups on its ring

Claim 1

A dye of the formula: ##STR30## wherein the 2-thienyl ring containing the ##STR31## group or groups is unsubstituted or substituted with 1 or 2 R 1 substituents independently selected from hydrogen, alkyl, alkoxy, aryl, thiocyano, formyl, alkylthio, carbamoyl, alkoxycarbonyl, alkylcarbamoyl, alkanoyl, alkylsulfonyl, aroyl, arylsulfonyl, sulfamoyl, SO 2 NH(alkyl), SO 2 N(dialkyl), alkylsulfonamido, alkanoylamino, halogen, trifluoromethyl, SO 3 (aryl), and arylazo; C is a coupler selected from ##STR32## wherein R 2 and R 14 each represents up to three groups selected from hydrogen, fluorine, chlorine, bromine, alkyl, cycloalkyl, alkoxy, phenoxy, alkylthio, arylthio, and radicals having the formula --NH--X--R 3 in which X is --CO--, --COO--, or --SO 2 -- and R 3 is selected from alkyl and alkyl substituted with halogen, hydroxy, phenoxy, aryl, cyano, cycloalkyl, alkylsulfonyl, alkylthio, alkanoyloxy, and alkoxy, and when X is --CO--, R 3 also is selected from hydrogen, amino, alkylamino, dialkylamino, arylamino, aryl, and furyl; R 4 and R 5 are each selected from hydrogen, alkyl, aryl, cycloalkyl, and alkyl substituted with halogen, CN, OH, alkoxy, aryloxy, alkoxyalkoxy, alkanoyl, alkanoyloxy, carbamoyl, alkylcarbamoyl, sulfamoyl, alkylsulfamoyl, alkoxyalkanoyloxy, and cycloalkyl, and R 4 and R 5 together represent a single, combined group --CH 2 CH 2 CH 2 CH 2 CH 2 --, --CH 2 CH 2 OCH 2 CH 2 --, --CH 2 CH 2 --S--CH 2 CH 2 --, or --CH 2 CH 2 --SO 2 --CH 2 CH 2 --; R 8 represents one or two groups each selected from hydrogen, alkyl and alkyl substituted with --CN, alkoxy, alkoxycarbonyl, alkoxycarbonyloxy, phenyl, cyclohexoxy, --OH, --Cl and Br; R 9 , R 10 and R 11 are each selected from hydrogen, alkyl, phenyl, or phenyl substituted with 1-3 groups selected from Cl, Br, alkyl or alkoxy, alkylthio, benzylthio, cyclohexylthio and phenylthio; Q and Q' are each selected from --CO--, --SO 2 --, or --CN; R 12 and R 13 are each selected from alkyl, hydroxyalkyl, alkoxy, alkoxycarbonylamino, trifluoromethyl, phenyl or phenyl substituted with 1-3 groups selected from Cl, Br, alkyl or alkoxy, alkoxycarbonylalkyl, cyanoalkyl, amino, haloalkyl, alkylamino, alkylthio, benzylthio, cyclohexylthio and phenylthio; and R 12 and R 13 together comprise --CH 2 C(CH 3 ) 2 CH 2 --, or 1,2--C 6 H 4 -- connecting Q and Q'; R 16 and R 17 are selected from hydrogen, cycloalkyl, aryl, alkyl, and alkyl substituted with alkoxy, hydroxy, alkoxyalkoxy, hydroxyalkoxy, carbamoyl, sulfamoyl, alkanoylamino, or alkenylsulfonyl, and aryl substituted with hydroxyalkyl; e is 1 or 2; t and t' are each 1 or zero; X' is 0, NH, N(alkyl)--, or N(aryl)--; Z is selected from straight- or branched-chain alkylene, and such alkylene substituted with phenyl, halogen, OSO 3 M, alkoxy or aryloxy groups, --CH 2 (CH 2 ) m V--CH 2 (CH 2 ) p --, where m is 1, 2 or 3, p is 0, 1, 2 or 3, and V is O, S, SO 2 , --SO 2 NH--, --SO 2 N(alkyl)--, --SO 2 N(aryl), --N(SO 2 aryl)--, --NH, --NHCO--, --NHCONH, --N(SO 2 alkyl), or --CON(alkyl); M is H, Na, K or NH 4 ; n is 1 or 2; and wherein each of the above alkyl and alkoxy groups contain from 0 to three of the following: hydroxy; halogen; cyano; succinimido; glutarimido; phthalimido; 2-pyrrolidono; cyclohexyl; phenyl or phenyl substituted with alkyl, alkoxy, halogen, alkanoylamino, cyano or alkoxycarbonyl; alkanoylamino; sulfamoyl; alkylsulfamoyl; vinylsulfonyl; acrylamido; phthalimidinyl; benzoylsulfonicimidyl; alkylsulfonamido; phenylsulfonamido; alkoxycarbonylamino; alkylcarbamoyloxy; alkoxycarbonyl; alkoxycarbonyloxy; ##STR33## wherein Y is --NH--, --NH--alkyl--, --O--, --S--, or --CH 2 O--; --S--R 6 , wherein R 6 is alkyl, phenyl, phenyl substituted with halogen, alkyl, alkoxy, alkanoylamino, cyano, or alkoxycarbonyl, pyridyl, pyrimidinyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, or ##STR34## --SO 2 R 3 ; --COOR 3 ; --OXR 3 ; --NH--X--R 3 ; --X--R 3 ; --SO 2 NR 7 R 7 ; wherein R 3 and X are as defined above and each R 7 is selected from H and R 3 ; alkoxy; alkoxy substituted with hydroxy, cyano, alkanoyloxy, or alkoxy; phenoxy; or phenoxy substituted with one or more of alkyl, alkoxy or halogen.