Photographic products and processes employing novel nondiffusible heterocyclylazonaphthol dye-releasing compounds

In a photographic assemblage comprising:

• (a) a support having thereon at least one photosensitive silver halide emulsion layer having associated therewith a dye image-providing material;
• (b) a dye image-receiving layer;
• and
• (c) an alkaline processing composition and means for discharging same within said assemblage;
• said assemblage containing a silver halide developing agent, the improvement wherein said dye image-providing material is a nondiffusible compound having at least one releasable 2-(2-heterocyclylazo)-1-naphthol dye moiety, said compound containing a ballasted carrier moiety which is capable of releasing said diffusible azo dye as a function of development of said silver halide emulsion layer under alkaline conditions, said heterocyclyl moiety containing a nitrogen atom adjacent to the point of attachment to the azo linkage, said heterocyclyl moiety not being substituted with a nitro group, and said heterocyclyl moiety being selected from the group consisting of pyridine, pyrimidine, quinoline, isoquinoline, pyrazine, pyridazine, thiazole, thiadiazole, triazole, benzothiazole and acinaphthothiazole.

In an integral photographic assemblage comprising:

• (a) a photosensitive element comprising a transparent support having thereon the following layers in sequence:
• a dye image-receiving layer, an alkaline solution-permeable, light-reflective layer, an alkaline solution-permeable, opaque layer, a red-sensitive silver halide emulsion layer having a ballasted cyan dye releaser associated therewith, a green-sensitive silver halide emulsion layer having a ballasted magenta dye releaser associated therewith, and a blue-sensitive silver halide emulsion layer having a ballasted yellow dye releaser associated therewith;
• (b) a transparent sheet superposed over said blue-sensitive silver halide emulsion layer and comprising a transparent support having thereon, in sequence, a neutralizing layer and a timing layer;
• and
• (c) a rupturable container containing an alkaline processing composition and an opacifying agent which is so positioned during processing of said assemblage that a compressive force applied to said container will effect a discharge of the container's contents between said transparent sheet and said blue-sensitive silver halide emulsion layer;
• said assemblage containing a silver halide developing agent;
• the improvement wherein at least one of said ballasted dye releasers is a nondiffusible compound having at least one releasable 2-(2-heterocyclylazo)-1-naphthol dye moiety, said compound containing a ballasted carrier moiety which is capable of releasing said diffusible azo dye as a function of development of said silver halide emulsion layer under alkaline conditions, said heterocyclyl moiety containing a nitrogen atom adjacent to the point of attachment to the azo linkage, said heterocyclyl moiety not being substituted with a nitro group, and said heterocyclyl moiety being selected from the group consisting of pyridine, pyrimidine, quinoline, isoquinoline, pyrazine, pyridazine, thiazole, thiadiazole, triazole, benzothiazole and acinaphthothiazole.

A process for producing a photographic transfer image in color in an imagewise-exposed photographic element comprising a support having thereon at least one photosensitive silver halide emulsion layer, said emulsion layer having associated therewith a nondiffusible compound having at least one releasable 2-(2-heterocyclylazo)-1-naphthol dye moiety, said compound containing a ballasted carrier moiety which is capable of releasing said diffusible azo dye as a function of development of said silver halide emulsion layer under alkaline conditions, said heterocyclyl moiety containing a nitrogen atom adjacent to the point of attachment to the azo linkage, said heterocyclyl moiety not being substituted with a nitro group, and said heterocyclyl moiety being selected from the group consisting of pyridine, pyrimidine, quinoline, isoquinoline, pyrazine, pyridazine, thiazole, thiadiazole, triazole, benzothiazole and acinaphthothiazole, said process comprising:

• (1) treating said photographic element with an alkaline processing composition in the presence of a silver halide developing agent to effect development of each of the exposed silver halide emulsion layers;
• (2) said dye-releasing compound then releasing said diffusible azo dye imagewise as a function of said development of each of said silver halide emulsion layers;
• (3) at least a portion of said imagewise distribution of said azo dye diffusing to a dye image-receiving layer;
• and
• (4) contacting said imagewise distribution of said azo dye in said dye image-receiving layer with metal ions, thereby forming a metal-complexed, azo dye transfer image.

A process for producing a photographic transfer image in color in an imagewise-exposed photographic element comprising a support having thereon at least one photosensitive silver halide emulsion layer, said emulsion layer having associated therewith a nondiffusible compound having at least one releasable 2-(2-heterocyclylazo)-1-naphthol dye moiety, said compound containing a ballasted carrier moiety which is capable of releasing said diffusible azo dye as a function of development of said silver halide emulsion layer under alkaline conditions, said heterocyclyl moiety containing a nitrogen atom adjacent to the point of attachment to the azo linkage, said heterocyclyl moiety not being substituted with a nitro group, and said heterocyclyl moiety being selected from the group consisting of pyridine, pyrimidine, quinoline, isoquinoline, pyrazine, pyridazine, thiazole, thiadiazole, triazole, benzothiazole and acinaphthothiazole, said ballasted carrier moiety being a group having the formula:

• ##STR128## wherein:
• (a) Ballast is an organic ballasting radical of such molecular size and configuration as to render said compound nondiffusible in said photographic element during development in an alkaline processing composition;
• (b) D is OR.sup.2 or NHR.sup.3 wherein R.sup.2 is hydrogen or a hydrolyzable moiety and R.sup.3 is hydrogen or a substituted or unsubstituted alkyl group 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 from 1 to 2 and is 2 when D is OR.sup.2 or when R.sup.3 is hydrogen or an alkyl group of less than 8 carbon atoms;
• and
• (e) L is a linking group which is [X--(NR.sup.4 --J).sub.q ].sub.m -- or X--J--NR.sup.4 -- wherein:
• (i) X represents a bivalent linking group of the formula --R.sup.5 --L'.sub.n --R.sup.5.sub.p -- where each R.sup.5 can be the same or different and each represents an alkylene radical having 1 to about 8 carbon atoms;
• a phenylene radical;
• or a substituted phenylene radical 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.sup.5 radicals does not exceed 14 carbon atoms;
• (v) R.sup.4 represents a hydrogen atom, or an alkyl radical 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;
• said process comprising:
• (1) treating said photographic element with an alkaline processing composition in the presence of a silver halide developing agent to effect development of each of the exposed silver halide emulsion layers, thereby oxidizing said developing agent;
• (2) said oxidized developing agent thereby cross-oxidizing said dye-releasing compound;
• (3) said cross-oxidized dye-releasing compound then cleaving as a result of alkaline hydrolysis to release said diffusible azo dye imagewise as a function of said imagewise exposure of each of said silver halide emulsion layers;
• (4) at least a portion of said imagewise distribution of said azo dye diffusing to a dye image-receiving layer;
• and
• (5) contacting said imagewise distribution of said azo dye with metal ions, thereby forming a metal-complexed, azo dye transfer image.