Nondiffusible heterocyclylazonaphthol dye-releasing compounds

Claim 2

A nondiffusible compound having at least one releasable 2-(2-heterocyclylazo)-1-naphthol dye moiety, said compound having the formula: ##STR114## wherein: G is hydroxy, a salt thereof, or a hydrolyzable precursor thereof; or a group which together with ##STR115## is CAR, said CAR being bonded to the naphthalene group through the oxygen of said ##STR116## group; Z represents the atoms necessary to complete a heterocyclyl moiety not being substituted with a nitro group, said heterocyclyl moiety being selected from the group consisting of pyridine, pyrimidine, quinoline, isoquinoline, pyrazine, pyridazine, thiazole, thiadiazole, triazole, benzothiazole and acinaphthothiazole; CAR represents a ballasted carrier moiety which will release said dye moiety as a function of development of a silver halide emulsion layer under alkaline conditions; and t is a positive integer of 1 to 2.

Claim 3

The compound of claim 1 wherein t is 1, G is OH and Z represents the atoms necessary to complete a pyridine, pyrimidine, pyrazine, quinoline or isoquinoline ring.

Claim 4

The compound of claim 1 wherein t is 1, G is OH, and Z represents the atoms necessary to complete a pyridine or pyrimidine ring.

Claim 5

The compound of claim 1 wherein G is hydroxy; or 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; or a group which together with ##STR117## is CAR, said CAR group being bonded to the naphthalene group through the oxygen of said ##STR118## group.

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: ##STR119## 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 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 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: ##STR120## wherein: Ballast is an organic ballasting radical of such molecular size and configuration as to render said compound non-diffusible 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: ##STR121## 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: ##STR122## 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: ##STR123## wherein: Ballast is an organic ballasting radical of such molecular size and configuration as to render said compound non-diffusible 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 to 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: ##STR124##

Claim 16

The compound of claim 1 which has the formula: ##STR125##