Substituted 5-acyl-3-carbamoyl-2-thienyl azo dyes with aniline, tetrahydroquinoline, and benzomorpholine couplers, process of manufacture, and polyamide testile materials dyed therewith

Claim 1

A compound of the formula ##STR460## in which R 4 is straight or branched alkylene, Z represents 1-3 groups selected from --OH, alkanoyloxy, alkoxy, alkoxycarbonyl, alkoxy-alkoxy, mono- and dialkylamino, --CN, carbamoyl, alkoxycarbonylamino, alkyl substituted carbamoyl, formamido, alkanoylamino, hydroxy substituted alkoxy, halogen, alkylthio, alkylsulfonyl, furyl, and pyrrolidono; R is selected from straight or branched alkyl, phenyl and phenyl substituted with straight or branched alkyl, halogen, or straight or branched alkoxy; R 2 is hydrogen or alkyl; and A is an azo dye coupler selected from ##STR461## wherein R 6 and R 7 are each selected from hydrogen, fluorine, chlorine, bromine, alkyl, cycloalkyl, alkoxy, phenoxy, 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 alkyl and alkyl substituted with halogen, hydroxy, phenoxy, aryl, cyano, cycloalkyl, alkylsulfonyl, alkylthio, alkanoyloxy, and alkoxy, and when X is --CO--, R 13 also is selected from hydrogen, amino, alkylamino, alkylcarbamoyl, dialkylamino, arylamino, aryl, and furyl; R 8 and R 9 are selected from hydrogen; cycloalkyl; cycloalkyl substituted with one or two groups selected from alkyl, --OH, alkoxy, halogen, or hydroxy substituted alkyl; phenyl; phenyl substituted with alkyl, alkoxy, halogen, alkanoylamino, cyano or alkoxycarbonyl; straight or branched 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; phenyl substituted with alkyl, alkoxy, halogen, alkanoylamino, cyano, or alkoxycabonyl; alkanoylamino; vinylsulfonyl; acrylamido; phthalimidinyl; benzoylsulfonicimidyl; alkylsulfonamido; phenylsulfonamido; alkoxycarbonylamino; alkylcarbamoyloxy; alkoxycarbonyloxy; ##STR462## wherein Y is --NH--, --NH-lower alkyl--, --O--, --S--, or --CH 2 O--; --S-R 14 wherein R 14 is alkyl, hydroxyalkyl, phenyl, phenyl substituted with halogen, alkyl, alkoxy, alkanoylamino, cyano, or alkoxycarbonyl, pyridyl, pyrimidinyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, or ##STR463## --SO 2 substituted with alkenyl, amino, cyclohexylamino, phenylamino, chloroalkylamino, alkyl, chloroalkyl, hydroxyalkyl, cyanoalkyl, cyclohexylalkyl, alkylsulfonylalkyl, alkylthioalkyl, alkanoyloxyalkyl, alkoxyalkyl, aminoalkyl, alkylaminoalkyl, alkylcarbamoylalkyl, dialkylaminoalkyl, phenylaminoalkyl, phenylalkyl, furylalkyl, alkylamino, morpholino, hydroxyalkylamino, or hydroxyalkyl-alkylamino; --OXR 13 ; --NH-X-R 13 ; --X-R 13 ; --CONR 15 R 15 ; wherein R 13 and X are as defined above and each R 15 is selected from H and R 13 ; alkoxy; alkoxy substituted with hydroxy, cyano, alkanoyloxy, or alkoxy; phenoxy; phenoxy substituted with one or more of alkyl, alkoxy or halogen; and R 8 and R 9 representing a single, combined group selected from pentamethylene, ethyleneoxyethylene and ethylenesulfonylethylene, which, with the nitrogen atom to which each is attached, forms a six membered ring; R 10 , R 11 and R 12 are each selected from hydrogen and alkyl; R 16 is selected from --OH, --Cl, --CONH 2 , --CONH-alkyl, alkoxy, phenoxy, --SR 14 , and --OXR 13 wherein R 13 and R 14 are as defined above; and wherein each of the above alkyl and alkylene moieties of the various groups where not otherwise specified contain from 1-6 carbons.