Diaryl pigments with improved heat stability and transparency containing coupled mixed bis-diazotized diamines and acid-substituted aromatic amines

Claim 1

A process for preparing a diaryl pigment having improved dried ink transparency and improved process heat stability, said pigment obtained by coupling a bis-diazotized compound having the formula A: ##STR19## wherein: R is selected from the group consisting of halogen, C 1 to C 3 alkyl or C 1 to C 4 alkoxy; with acetoacetanilides having the formula B-1 or B-2, or with pyrazolinones having the formula B-3, as well as mixtures of combinations of B-1, B-2 or B-3: ##STR20## in which the R 1 s are independently selected from the group consisting of hydrogen, hydroxy, C 1 to C 4 alkyl, C 1 to C 4 alkoxy, NO 2 , halogen and ##STR21## and n denotes an integer from 1-3, and ##STR22## in which R 2 and R 3 each denote the radical: ##STR23## wherein R 3 ' is a C 1 to C 6 alkyl group, or one of the radicals R 2 and R 3 denotes a hydrogen atom and the other denotes a radical selected from the group consisting of: ##STR24## wherein R 3' has the meaning given above, or R 2 and R 3 linked to one another denote a divalent radical selected from the group consisting of: ##STR25## the terminal bonds being attached to the phenyl nucleus at the 3 position and the 4 position, and ##STR26## in which R 4 denotes a phenyl group or a C 1 to C 3 alkyl substituted phenyl group, and R 5 denotes hydrogen or a C 1 to C 3 alkyl group, and with a diazotized primary aromatic amine having the formulas C-1, C-2, C-3 C-4 or C-5, as well as mixtures of such amines: ##STR27## wherein Y is a carboxylic acid group or a sulfonic acid group or a salt thereof, R 6 is selected from the group consisting of halogen, hydrogen, C 1 to C 4 alkyl, carboxylic acid or alkali or alkaline earth metal salt thereof, sulfonic acid or alkali or alkaline earth metal salt thereof, amino, aryl, and OR 7 wherein R 7 is aryl or C 1 to C 4 alkyl, X is C, N, O or S, and m is an integer of 1 or 2, ##STR28## wherein Y, R 6 and m have the meanings set forth above, ##STR29## wherein R 6 and Y have the meanings given above, ##STR30## wherein R 6 and Y have the meanings given above and B and D are independently selected from the group consisting of O, N, C and (CH 2 )p where p denotes an integer of 1 or 2, ##STR31## wherein R 6 , B, D, Y and m have the meanings given above, the amount of component B-2 and/or B-3 present in the composition when a mixture of B-1 and B-2 and/or B-3 is employed being in the range of from about 0.5 to about 10 mol % based on the quantity of B-1, B-2 and/or B-3 taken together, and the amount of component C being from about 0.25 to about 15 mol % of the pigment, said process comprising: a. diazotizing compounds having the formula of the categories A and C; b. coupling a mixture of the resulting diazonium salts with a compound having the formula B-1, B-2, or B 3 or mixtures of B-1, B-2, B-3; c. filtering and washing the resulting product; and d. heating said product in air to a temperature of at least about 90° C. to dry said product.