An azo compound of the structure X--N.dbd.N--C' wherein X is selected from ##STR72## wherein one or two substituents R.sup.1 through R.sup.13 on each radical is an ester group of the structure --Z--O--R wherein Z is either ##STR73## and R is a lower alkyl group, straight chain, branched chain or alicyclic, and which is substituted with 1-3 fluorine atoms;
- R.sup.1 is hydrogen, halogen, cyano, nitro, formyl, lower alkanoyl, benzoyl, lower alkoxycarbonyl, lower alkylsulfonyl, sulfamoyl, lower alkylsulfamoyl, carbamoyl, lower alkylcarbamoyl, or trifluoromethyl;
- R.sup.2 is halogen, cyano, lower alkylsulfonyl, formyl, lower alkanoyl, benzoyl, lower alkoxycarbonyl, sulfamoyl, lower alkylsulfamoyl, carbamoyl, lower alkylcarbamoyl, trifluoromethyl, or nitro;
- R.sup.3 is hydrogen, halogen, cyano or nitro;
- R.sup.6 is cyano, nitro, aryl, lower alkanoyl, aroyl, lower alkoxycarbonyl, lower hydroxyalkoxycarbonyl, lower alkoxy-lower-alkoxycarbonyl, or the group 13 CONR.sup.4' R.sup.5' in which R.sup.4' individually is hydrogen, lower alkyl, cyclohexyl, lower alkylcyclohexyl, cyclohexylmethyl, lower alkylcyclohexylmethyl, lower hydroxyalkylcyclohexylmethyl, aryl-lower-alkyl, or aryl;
- R.sup.5' individually is hydrogen or lower alkyl;
- and R.sup.4' and R.sup.5' in combination are pentamethylene or ethyleneoxyethylene;
- R.sup.5 is hydrogen, lower alkyl, lower alkoxy, aryl-lower-alkyl or aryl;
- R.sup.4 is selected from R.sup.1, lower alkyl, thiocyanato and arylazo;
- R.sup.7 is hydrogen, lower alkyl, lower alkoxy, nitro, halogen, lower alkylsulfonyl, carbamoyl, lower alkylcarbamoyl, lower alkoxycarbonyl, sulfamoyl, lower alkylsulfamoyl, cyano, thiocyanato, trifluoromethyl or phenyl;
- R.sup.8 is hydrogen, lower alkyl, lower alkoxy, nitro, halogen, lower alkylsulfonyl, substituted lower alkylsulfonyl, carbamoyl, lower alkylcarbamoyl, lower alkoxycarbonyl, sulfamoyl, lower alkylsulfamoyl, cyano, thiocyanato, lower alkylthio, cyclohexylthio, phenylthio or trifluoromethyl;
- R.sup.9 and R.sup.10 are fluorinated ester groups of the formula --Z--O--R;
- R.sup.12 is hydrogen, cyano, or lower alkyl;
- R.sup.13 is cyano, carbamoyl, nitro, or lower alkoxycarbonyl;
- R.sup.14 is hydrogen, lower alkyl, phenyl, phenyl substituted with halogen, lower alkyl, lower alkoxy, lower alkanoylamino, cyano, or lower alkoxycarbonyl, lower alkylsulfonyl, phenylsulfonyl, phenylsulfonyl substituted with halogen, lower alkyl, lower alkoxy, lower alkanoylamino, cyano, or lower alkoxycarbonyl;
- and m is 1 or 2;
- and C' is an aniline, tetrahydroquinoline, or benzomorpholine type coupler selected from those of the formulae ##STR74## wherein R.sup.15 and R.sup.16 are each selected from hydrogen, fluorine, chlorine, bromine, lower alkyl, cycloalkyl, lower alkoxy, trifluoromethyl, phenoxy, lower alkylthio, arylthio, and radicals having the formula --NH--X'--R.sup.23 in which X' is --CO--, --COO--, or --SO.sub.2 --, and R.sup.23 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.sup.23 is further selected from hydrogen, amino, lower alkylamino, lower alkylcarbamoyl, lower dialkylamino, arylamino, aryl, furfuryl and furyl;
- R.sup.17 and R.sup.18 are selected from hydrogen;
- cycloalkyl;
- cycloalkyl substituted with one or two groups selected from lower alkyl, --OH, lower alkoxy, halogen and 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;
- amino;
- succinimido;
- glutarimido;
- phthalimido;
- 2-pyrrolidono;
- cyclohexyl;
- phenyl or phenyl substituted with lower alkyl, lower alkoxy, halogen, lower alkanoylamino, cyano or lower alkoxycarbonyl;
- lower alkanoyloxy;
- lower alkanoylamino;
- sulfamoyl;
- lower alkylsulfamoyl;
- vinylsulfonyl;
- acrylamido;
- phthalimidinyl;
- benzoylsulfonicimidyl;
- lower alkylsulfonamido;
- phenylsulfonamido;
- lower alkoxycarbonylamino;
- lower alkylcarbamoyloxy;
- lower alkoxycarbonyl;
- lower alkoxycarbonyloxy;
- lower alkenylcarbonylamino;
- ##STR75## Wherein Y is --NH--, ##STR76## --O--, --S--, or --CH.sub.2 O--;
- --S--R.sup.24 wherein R.sup.24 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 ##STR77## --SO.sub.2 R.sup.23 ;
- --COOR.sup.23 ;
- --OX'R.sup.23 ;
- --NH--X'--R.sup.23 ;
- --X'--R.sup.23 ;
- --OCO--R.sup.23 ;
- --CONR.sup.25 R.sup.25 ;
- --SO.sub.2 NR.sup.25 R.sup.25 ;
- wherein R.sup.23 and X' are as defined above and each R.sup.25 is selected from H and R.sup.23 ;
- 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.sup.17 and R.sup.18 combined in the aniline couplers to form with the nitrogen atom a ring containing pentamethylene, ethyleneoxyethylene or ethylenesulfonylethylene groups;
- R.sup.19, R.sup.20, R.sup.21 and R.sup.22 are each selected from hydrogen and lower alkyl.