Azo dyes containing a diazotized 5-amino isothiazol moiety having thereon a sulfonic acid or salt group

A dye of the formula:

• ##STR18## wherein R.sup.1 is hydrogen or alkyl;
• M is H.sup.+, Na.sup.+, Li.sup.+, K.sup.+ or NH.sub.4.sup.+ ;
• and C is a coupler selected from ##STR19## wherein R.sup.2 and R.sup.14 each independently represents hydrogen or 1-3 substituents selected from fluorine, chlorine, bromine, alkyl, cycloalkyl, alkoxy, phenoxy, alkylthio, arylthio, and radicals having the formula --NH--X--R.sup.3 in which X is --CO--, --COO--, or --SO.sub.2 -- and R.sup.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.sup.3 also is selected from hydrogen, amino, alkylamino, alkylcarbamoyl, dialkylamino, arylamino, aryl, and furyl;
• R.sup.4 and R.sup.5 are each selected from hydrogen, alkyl, aryl, cycloalkyl, and R.sup.4 and R.sup.5 combined as --CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 --, --CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 --, --CH.sub.2 CH.sub.2 --S--CH.sub.2 CH.sub.2 --, or --CH.sub.2 CH.sub.2 --SO.sub.2 --CH.sub.2 CH.sub.2 --;
• R.sup.8 is one or two groups each selected from hydrogen, alkyl and alkyl substituted with --CN, alkoxy, alkoxycarbonyl, alkoxycarbonyloxy, phenyl, cyclohexoxy, --OH, --Cl and Br;
• R.sup.9, R.sup.10 and R.sup.11 are each selected from hydrogen, alkyl, phenyl, phenyl substituted with 1-3 substituents selected from Cl, Br, alkyl and alkoxy, alkylthio, benzylthio, cyclohexylthio, and phenylthio;
• Q and Q' are each selected from --CO--, --SO.sub.2, and --CN;
• R.sup.12 and R.sup.13 are each selected from hydrogen, alkyl, hydroxyalkyl, alkoxy, alkoxycarbonylamino, trifluoromethyl, phenyl, phenyl substituted with 1-3 substituents selected from Cl, Br, alkyl and alkoxy, alkoxycarbonylalkyl, cyanoalkyl, amino, haloalkyl, alkylamino, alkylthio, benzylthio, cyclohexylthio, phenylthio, and R.sup.12 and R.sup.13 combined as an alkylene bridge of 2 or 3 carbons or as an arylene or cycloalkylene radical of 5-6 carbons connecting Q and Q';
• R.sup.16 and R.sup.17 are selected from hydrogen, cycloalkyl, aryl, alkyl, alkyl substituted with alkoxy, hydroxy, alkoxyalkoxy, hydroxyalkoxy, carbamoyl, sulfamoyl, acylamido, or alkylsulfonyl, and aryl substituted with hydroxyalkyl;
• e is 1 or 2;
• t and t' are each 1 or zero and when t or t' is zero, the corresponding Q or Q' group is --CN;
• and wherein each of the aliphatic portions of the above alkyl, cycloaliphatic, alkoxy, alkanoyl, aryl and aryloxy groups are unsubstituted or substituted with 1-3 of the following:
• hydroxy;
• halogen;
• cyano;
• succinimido;
• glutarimido;
• phthalimido;
• 2-pyrrolidono;
• cyclohexyl;
• phenyl;
• phenyl substituted with alkyl, alkoxy, halogen, alkanoylamino, cyano or alkoxycarbonyl;
• alkanoylamino;
• vinylsulfonyl;
• acrylamido;
• phthalimidinyl;
• benzoylsulfonicimidyl;
• alkylsulfonamido;
• phenylsulfonamido;
• alkoxycarbonylamino;
• alkylcarbamoyloxy;
• alkoxycarbonyl;
• alkoxycarbonyloxy;
• ##STR20## wherein Y is --NH--, --NH--alkyl--, --O--, --S--, or --CH.sub.2 O--;
• --S--R.sup.6 wherein R.sup.6 is alkyl, phenyl, phenyl substituted with halogen, alkyl, alkoxy, alkanoylamino, cyano, or alkoxycarbonyl, pyridyl, pyrimidinyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, or ##STR21## --OXR.sup.3 ;
• --NH--X--R.sup.3 ;
• --X--R.sup.3 ;
• --CONR.sup.7 R.sup.7 ;
• --SO.sub.2 NR.sup.7 R.sup.7 ;
• wherein R.sup.3 and X are as defined above and each R.sup.7 is selected from H and R.sup.3 ;
• alkoxy;
• alkoxy substituted with hydroxy, cyano, alkanoyloxy, or alkoxy;
• phenoxy or phenoxy substituted with one or more of alkyl, alkoxy or halogen.