Photographic products and processes employing novel nondiffusible 2-(2-pyridylazo)-4,5-bis(tertiary amino)phenol black dye-releasing compounds and precursors thereof

In a photographic element comprising a support having thereon a photosensitive silver halide emulsion layer, said emulsion layer having associated therewith a dye image-providing material, the improvement wherein said dye image-providing material is a nondiffusible compound having a releasable, 2-(2-pyridylazo)-4,5-bis(tertiary amino)phenol black dye moiety or precursor thereof, said compound having the formula:

• ##STR20## wherein:
• (a) R represents hydrogen, a hydrolyzable moiety or CAR;
• (b) R.sup.1 and R.sup.2 each independently represents an alkyl group of 1 to about 6 carbon atoms, CAR, or can be taken together with the nitrogen to which they are attached to complete a 5- or 6-membered heterocyclic ring;
• (c) R.sup.3 and R.sup.4 each independently represents an alkyl group of 1 to about 6 carbon atoms, CAR, or can be taken together with the nitrogen to which they are attached to complete a 5- or 6-membered heterocyclic ring;
• (d) CAR represents a ballasted carrier moiety capable of releasing said diffusible black dye moiety or precursor thereof as a function of development of said silver halide emulsion layer under alkaline conditions;
• and
• (e) n is 0, 1 or 2, with the proviso that when n is 0, then at least one of R, R.sup.1, R.sup.2, R.sup.3, or R.sup.4 is CAR.

In a photographic assemblage comprising:

• (a) a support having thereon a photosensitive silver halide emulsion layer having associated therewith a dye image-providing material;
• and
• (b) a dye image-receiving layer;
• the improvement wherein said dye image-providing material is a nondiffusible compound having a releasable, 2-(2-pyridylazo)-4,5-bis(tertiary amino)phenol black dye moiety or precursor thereof, said compound having the formula:
• ##STR27## wherein:
• (a) R represents hydrogen, a hydrolyzable moiety or CAR;
• (b) R.sup.1 and R.sup.2 each independently represents an alkyl group of 1 to about 6 carbon atoms, CAR, or can be taken together with the nitrogen to which they are attached to complete a 5- or 6-membered heterocyclic ring;
• (c) R.sup.3 and R.sup.4 each independently represents an alkyl group of 1 to about 6 carbon atoms, CAR, or can be taken together with the nitrogen to which they are attached to complete a 5- or 6-membered heterocyclic ring;
• (d) CAR represents a ballasted carrier moiety capable of releasing said diffusible black dye moiety or precursor thereof as a function of development of said silver halide emulsion layer under alkaline conditions;
• and
• (e) n is 0, 1 or 2, with the proviso that when n is 0, then at least one of R, R.sup.1, R.sup.2, R.sup.3, or R.sup.4 is CAR.

In a photographic assemblage comprising:

• (a) a support having thereon a photosensitive silver halide emulsion layer having associated therewith a dye image-providing material;
• and
• (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 a releasable, 2-(2-pyridylazo)-4,5-bis(tertiary amino)phenol black dye moiety or precursor thereof, said compound having the formula:
• ##STR28## wherein:
• (a) R represents hydrogen, a hydrolyzable moiety or CAR;
• (b) R.sup.1 and R.sup.2 each independently represents an alkyl group of 1 to about 6 carbon atoms, CAR, or can be taken together with the nitrogen to which they are attached to complete a 5- or 6-membered heterocyclic ring;
• (c) R.sup.3 and R.sup.4 each independently represents an alkyl group of 1 to about 6 carbon atoms, CAR, or can be taken together with the nitrogen to which they are attached to complete a 5- or 6-membered heterocyclic ring;
• (d) CAR represents a ballasted carrier moiety capable of releasing said diffusible black dye moiety or precursor thereof as a function of development of said silver halide emulsion layer under alkaline conditions;
• and
• (e) n is 0, 1 or 2, with the proviso that when n is 0, then at least one of R, R.sup.1, R.sup.2, R.sup.3, or R.sup.4 is CAR.

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, and a silver halide emulsion layer having a ballasted dye releaser associated therewith;
• (b) a transparent sheet superposed over said 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 compressive force applied to said container will effect a discharge of the container's contents between said transparent sheet and said silver halide emulsion layer;
• said assemblage containing a silver halide developing agent;
• the improvement wherein said ballasted dye releaser is a nondiffusible compound having a releasable, 2-(2-pyridylazo)-4,5-bis(tertiary amino)phenol black dye moiety or precursor thereof, said compound having the formula:
• ##STR29## wherein:
• (a) R represents hydrogen, a hydrolyzable moiety or CAR;
• (b) R.sup.1 and R.sup.2 each independently represents an alkyl group of 1 to about 6 carbon atoms, CAR, or can be taken together with the nitrogen to which they are attached to complete a 5- or 6-membered heterocyclic ring;
• (c) R.sup.3 and R.sup.4 each independently represents an alkyl group of 1 to about 6 carbon atoms, CAR, or can be taken together with the nitrogen to which they are attached to complete a 5- or 6-membered heterocyclic ring;
• (d) CAR represents a ballasted carrier moiety capable of releasing said diffusible black dye moiety or precursor thereof as a function of development of said silver halide emulsion layer under alkaline conditions;
• and
• (e) n is 0, 1 or 2, with the proviso that when n is 0, then at least one of R, R.sup.1, R.sup.2, R.sup.3, or R.sup.4 is CAR.

A process for producing a photographic transfer image in in an imagewise-exposed photographic element comprising a support having thereon a photosensitive silver halide emulsion layer, said emulsion layer having associated therewith a non-diffusible compound having a releasable, 2-(2-pyridylazo)-4,5-bis(tertiary amino)phenol black dye moiety or precursor thereof, said compound having the formula:

• ##STR30## wherein:
• (a) R represents hydrogen, a hydrolyzable moiety or CAR;
• (b) R.sup.1 and R.sup.2 each independently represents an alkyl group of 1 to about 6 carbon atoms, CAR, or can be taken together with the nitrogen to which they are attached to complete a 5- or 6-membered heterocyclic ring;
• (c) R.sup.3 and R.sup.4 each independently represents an alkyl group of 1 to about 6 carbon atoms, CAR, or can be taken together with the nitrogen to which they are attached to complete a 5- or 6-membered heterocyclic ring;
• (d) CAR represents a ballasted carrier moiety capable of releasing said diffusible black dye moiety or precursor thereof as a function of development of said silver halide emulsion layer under alkaline conditions;
• and
• (e) n is 0, 1 or 2, with the proviso that when n is 0, then at least one of R, R.sup.1, R.sup.2, R.sup.3, or R.sup.4 is CAR;
• said process comprising:
• (a) treating said photographic element with an alkaline processing composition in the presence of a silver halide developing agent to effect development of the exposed silver halide emulsion layer;
• (b) said dye-releasing compound then releasing said diffusible 2-(2-pyridylazo)-4,5-bis(tertiary amino)phenol black dye or precursor thereof imagewise as a function of said development of said silver halide emulsion layer;
• (c) at least a portion of said imagewise distribution of said black dye or precursor thereof diffusing to a dye image-receiving layer;
• and
• (d) contacting said imagewise distribution of said black dye or precursor thereof with metal ions, thereby forming a metal-complexed, 2-(2-pyridylazo)-4,5-bis(tertiary amino)phenol black dye transfer image.