Nondiffusible azo dye-releasing compounds

Claim 2

A nondiffusible compound having at least one diffusible azo dye moiety, said compound having the formula: ##STR27## wherein: G is a metal chelating group, a salt thereof or a hydrolyzable precursor thereof; or a group which together with a ##STR28## group is CAR, said CAR being bonded to the benzene ring through the oxygen of said ##STR29## group; G 1 is hydroxy, a salt thereof, or a hydrolyzable precursor thereof; Z is an electron withdrawing group having the formula --CON(R) 2 , --SO 2 N(R) 2 , --COOR, --CN, SO 2 R' or --COR', wherein R' is alkyl of 1 to 8 carbon atoms or aryl of 6 to 10 carbon atoms, and each R is H or R'; Z' is alkyl of 1 to 8 carbon atoms, aryl of 6 to 10 carbon atoms or N(R) 2 ; CAR represents a ballasted carrier moiety which will release said diffusible azo dye as a function of development of a silver halide emulsion layer under alkaline conditions; and t is an integer of 0 to 1, with the proviso that the compound contains at least one but not more than two CAR groups.

Claim 3

The compound of claim 1 wherein t is 1 and G is OH, G 1 is OH, Z is --CON(R) 2 and Z' is alkyl of 1 to 8 carbon atoms.

Claim 4

The compound of claim 1 wherein G 1 is a hydrolyzable precursor comprising an acyloxy group having the formula --OCOR 1 , --OCOOR 1 , or --OCON(R 1 ) 2 , wherein each R 1 is alkyl having 1 to about 8 carbon atoms or aryl having 6 to about 12 carbon atoms.

Claim 5

The compound of claim 1 wherein G is hydroxy; amino; carboxy; sulfonamido; sulfamoyl; a fused nitrogen-containing ring; or a hydrolyzable ester group having the formula --OCOR 1 , --OCOOR 1 , or --COOR 1 , wherein R 1 is alkyl having 1 to about 8 carbon atoms or aryl having 6 to about 12 carbon atoms.

Claim 6

The compound of claim 1 wherein said CAR is a group having the formula: (Ballast-Carrier-Link) - wherein: (a) Ballast is an organic ballasting radical of such molecular size and configuration as to render said compound nondiffusible in a photographic element during development in an alkaline processing composition; (b) Carrier is an oxidiable acyclic, carbocyclic or heterocyclic moiety; and (c) Link represents a group which, upon oxidation of said carrier moiety, is capable of being hydrolytically cleaved to release said diffusible azo dye.

Claim 7

The compound of claim 5 wherein the Carrier moiety contains atoms according to the following configuration: a (--C═C).sub.b -- wherein: b is a positive integer of 1 to 2; and a represents the radicals OH, SH, NH--, or hydrolyzable precursors thereof.

Claim 8

The compound of claim 1 wherein said CAR is a group having the formula: ##STR30## wherein: (a) Ballast is an organic ballasting radical of such molecular size and configuration as to render said compound nondiffusible in a photographic element during development in an alkaline processing composition; (b) D is OR 2 or NHR 3 wherein R 2 is hydrogen or a hydrolyzable moiety and R 3 is hydrogen or substituted or unsubstituted alkyl of 1 to 22 carbon atoms; (c) Y represents the atoms necessary to complete a benzene nucleus, a naphthalene nucleus, or a 5 to 7 membered heterocyclic ring; (d) j is a positive integer of 1 to 2 and is 2 when D is OR 2 or NHR 3 when R 3 is hydrogen or alkyl of less than 8 carbon atoms; and (e) L is a linking group which is [X---(NR 4 --J) q ] m -- or X--J--NR 4 -- wherein: (i) X represents a bivalent linking group of the formula --R 5 --L' n --R 5 p -- where each R 5 can be the same or different and each represents alkylene having 1 to about 8 carbon atoms; phenylene; or substituted phenylene having 6 to about 9 carbon atoms; (ii) L' represents a bivalent radical selected from oxy, carbonyl, carboxamido, carbamoyl, sulfonamido, ureylene, sulfamoyl, sulfinyl or sulfonyl; (iii) n is an integer of 0 or 1; (iv) p is 1 when n equals 1 and p is 1 or 0 when n equals 0, provided that when p is 1 the carbon content of the sum of both R 5 radicals does not exceed 14 carbon atoms; (v) R 4 represents hydrogen, or alkyl having 1 to about 6 carbon atoms; (vi) J represents a bivalent radical selected from sulfonyl or carbonyl; (vii) q represents an integer of 0 or 1; and (viii) m represents an integer of 0, 1 or 2.

Claim 9

The compound of claim 7 wherein D is OH, j is 2, Y is a naphthalene nucleus, G is OH, G 1 is OH and t is 1.

Claim 10

The compound of claim 1 wherein said CAR will release said diffusible azo dye as an inverse function of development of a silver halide emulsion layer under alkaline conditions.

Claim 11

The compound of claim 9 wherein said CAR is a group having the formula: ##STR31## wherein: Ballast is an organic ballasting radical of such molecular size and configuration as to render said compound nondiffusible in a photographic element during said development in an alkaline processing composition; W 1 represents at least the atoms necessary to complete a quinone nucleus; r is a positive integer of 1 or 2; R 6 is alkyl having 1 to about 40 carbon atoms or aryl having 6 to about 40 carbon atoms; and k is a positive integer of 1 to 2 and is 2 when R 6 has less than 8 carbon atoms.

Claim 12

The compound of claim 9 wherein said CAR is a group having the formula: ##STR32## wherein: Ballast is an organic ballasting radical of such molecular size and configuration as to render said compound nondiffusible in a photographic element during said development in an alkaline processing composition; W 2 represents at least the atoms necessary to complete a benzene nucleus; and R 7 is alkyl having 1 to about 4 carbon atoms.

Claim 13

The compound of claim 9 wherein said CAR is a group having the formula: ##STR33## wherein: Ballast is an organic ballasting radical of such molecular size and configuration as to render said compound nondiffusible in a photographic element during said development in an alkaline processing composition; W 2 represents at least the atoms necessary to complete a benzene nucleus; and R 7 is alkyl having 1 to about 4 carbon atoms.

Claim 14

The compound of claim 9 wherein said CAR is a group having the formula: ##STR34## wherein: Ballast is an organic ballasting radical of such molecular size and configuration as to render said compound nondiffusible in a photographic element during said development in an alkaline processing composition; W 2 represents at least the atoms necessary to complete a benzene nucleus; r is a positive integer of 1 or 2; R 6 is alkyl having 1 to about 40 carbon atoms or aryl having 6 to about 40 carbon atoms; k is a positive integer of 1 to 2 and is 2 when R 6 has less than 8 carbon atoms; and K is OH or a hydrolyzable precursor thereof.

Claim 15

The compound of claim 1 which has the formula: ##STR35##

Claim 16

The compound of claim 1 which has the formula: ##STR36##

Claim 17

The compound of claim 1 which has the formula: ##STR37##