Azo dyes from 2-amino-5-styryl-1,3,4-thiadiazoles

Claim 2

Compounds having the formula ##STR70## in which R is selected from --H, --NO 2 , --CN, --Cl, and --Br, alkoxy of 1-8 carbons, alkyl of 1-8 carbons, alkoxycarbonyl of 1-8 carbons, or CF 3 ; and A is an aniline, tetrahydroquinoline, or benzomorpholine azo dye coupler moiety.

Claim 3

The compounds according to claim 1 wherein R is --H or --NO 2 ;

Claim 4

The azo compounds of claim 1 wherein the A coupler moieties have the formulae ##STR71## wherein R 6 and R 7 are each selected from hydrogen, fluorine, chlorine, bromine, lower alkyl, cycloalkyl, lower alkoxy, phenoxy, lower alkylthio, arylthio, and radicals having the formula --NH--X--R 13 in which X is --CO--, --COO--, or --SO 2 -- and R 13 is selected from lower alkyl and lower alkyl substituted with halogen, hydroxy, phenoxy, aryl, cyano, cycloalkyl, lower alkylsulfonyl, lower alkylthio, lower alkanoyloxy, and lower alkoxy, and when X is --CO--, R 13 also can be hydrogen, amino, lower alkylamino, lower alkylcarbamoyl, lower dialkylamino, arylamino, aryl, or furyl; R 8 and R 9 are selected from halogen; cycloalkyl; cycloalkyl substituted with one or two groups selected from lower alkyl, --OH, lower alkoxy, halogen, or hydroxy substituted lower alkyl; phenyl or phenyl substituted with lower alkyl, lower alkoxy, halogen, lower alkanoylamino, cyano or lower alkoxycarbonyl; straight or branched lower alkenyl; straight or branched alkyl of 1-8 carbons and such alkyl substituted with the following: hydroxy; halogen; cyano; succinimido; glutarimido; phthalimido; 2-pyrrolidono; cyclohexyl; phenyl or phenyl substituted with lower alkyl, lower alkoxy, halogen, lower alkanoylamino, cyano or lower alkoxycarbonyl; lower alkanoylamino; sulfamoyl; lower alkylsulfamoyl; vinylsulfonyl; acrylamido; phthalimidinyl; benzoylsulfonicimidyl; lower alkylsulfonamido; phenylsulfonamido; lower alkoxycarbonylamino; lower alkylcarbamoyloxy; lower alkoxycarbonyl; lower alkoxycarbonyloxy; ##STR72## wherein Y is --NH--, --NH-lower alkyl-, --O--, --S--, or --CH 2 O--; --S--R 14 wherein R 14 is lower alkyl, phenyl, phenyl substituted with halogen, lower alkyl, lower alkoxy, lower alkanoylamino, cyano, or lower alkoxycarbonyl, pyridyl, pyrimidinyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, triazolyl, or ##STR73## --SO 2 R 13 ; --COOR 13 ; --OXR 13 ; --NH--X--R 13 ; --X--R 13 ; --OCO--R 13 ; --CONR 15 R 15 ; --SO 2 NR 15 R 15 ; wherein R 13 and X are as defined above and each R 15 is selected from H and R 13 ; lower alkoxy; lower alkoxy substituted with hydroxy, cyano, lower alkanoyloxy, or lower alkoxy; phenoxy; phenoxy substituted with one or more of lower alkyl, lower alkoxy or halogen; and R 8 and R 9 represent a single, combined group which, with the nitrogen atom to which each is attached, forms a ring; R 10 , R 11 and R 12 are each selected from hydrogen and lower alkyl; and R 16 is selected from --OH, --Cl, --CONH 2 , --CONH-lower alkyl, lower alkoxy, phenoxy, --SR 14 , and --OXR 13 wherein R 13 and R 14 are as defined above.

Claim 5

Azo compounds according to claim 1 wherein R is hydrogen or --NO 2 ; and A is a coupler moiety of one of the formulae ##STR74## wherein R 6 is lower alkyl, lower alkoxy, lower alkanoylamino, or lower alkoxycarbonylamino; R 7 is hydrogen, lower alkyl, or lower alkoxy; R 8 and R 9 are the same or different and selected from hydrogen, lower alkyl, lower alkyl substituted with hydroxy, alkoxy, alkoxyalkoxy, hydroxyalkoxy, carbamoyl, lower alkylcarbamoyl, lower alkanoylamino, sulfamoyl, lower alkylsulfamoyl, phenyl, cyclohexyl, 2-pyrrolidono, phthalimido, succinimido, cyano, phenoxy, alkylsulfonyl, phthalimidinyl, benzoylsulfonicimidyl, triazolylthio, lower alkylsulfonamido, --SO 2 NH 2 , --SO 2 NHR, phenylsulfonamido, lower alkoxycarbonylamino, lower alkylcarbamoyloxy, lower alkoxycarbonyl, lower alkoxycarbonyloxy; ##STR75## R 10 and R 12 are each hydrogen or lower alkyl.

Claim 6

An azo compound according to claim 1 having the formula ##STR76##

Claim 7

An azo compound according to claim 1 having the formula ##STR77##

Claim 8

An azo compound according to claim 1 having the formula ##STR78##

Claim 9

An azo compound according to claim 1 having the formula ##STR79##

Claim 10

An azo compound according to claim 1 having the formula ##STR80##

Claim 11

An azo compound according to claim 1 having the formula ##STR81##

Claim 12

An azo compound according to claim 1 having the formula ##STR82##

Claim 13

An azo compound according to claim 1 having the formula ##STR83##

Claim 14

An azo compound according to claim 1 having the formula ##STR84##

Claim 15

An azo compound according to claim 1 having the formula ##STR85##