US 4,142,891 A · Photographic products and processes employing nondiffusible azo dye-releasing compounds

A 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 a releasable azo dye moiety, said compound having the following formula:

##STR27## wherein:
Z represents the atoms necessary to complete an aromatic carbocyclic or heterocyclic nucleus having at least one ring of 5 to 7 atoms;
Z' is an aromatic carbocyclic or heterocyclic nucleus having at least one ring of 5 to 7 atoms, said Z' having, in a position adjacent to the point of attachment to the azo linkage, either (a) a nitrogen atom in said ring of said nucleus which acts as a chelating site, or (b) a carbon atom in said ring of said nucleus having directly attached thereto a nitrogen atom which acts as a chelating site;
G is a metal chelating group, a salt thereof or a hydrolyzable precursor thereof;
said compound also containing a ballasted carrier moiety capable of releasing said diffusible azo dye as a function of development of said silver halide emulsion layer under alkaline conditions.

2 more elements

A 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 a releasable 7 arylazo-pyrazolotriazole dye moiety, said compound containing:

(a) in the ortho position of the arylazo moiety a metal chelating group, a salt thereof or a hydrolyzable precursor thereof, and
(b) a ballasted carrier moiety which is capable of releasing said diffusible arylazo-pyrazolotriazole dye as a function of development of said silver halide emulsion layer under alkaline conditions.

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 a releasable azo dye moiety, said compound having the following formula:
##STR53## wherein:
Z represents the atoms necessary to complete an aromatic carbocyclic or heterocyclic nucleus having at least one ring of 5 to 7 atoms;
Z' is an aromatic carbocyclic or heterocyclic nucleus having at least one ring of 5 to 7 atoms, said Z' having, in a position adjacent to the point of attachment to the azo linkage, either (a) a nitrogen atom in said ring of said nucleus which acts as a chelating site, or (b) a carbon atom in said ring of said nucleus having directly attached thereto a nitrogen atom which acts as a chelating site;
G is a metal chelating group, a salt thereof or a hydrolyzable precursor thereof;
said compound also containing a ballasted carrier moiety capable of releasing said diffusible azo dye as a function of development of said silver halide emulsion layer under alkaline conditions.

7 more elements

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 one of said ballasted dye releasers is a nondiffusible compound having a releasable azo dye moiety, said compound having the following formula:
##STR61## wherein:
Z represents the atoms necessary to complete an aromatic carbocyclic or heterocyclic nucleus having at least one ring of 5 to 7 atoms;
Z' is an aromatic carbocyclic or heterocyclic nucleus having at least one ring having of 5 to 7 atoms, said Z' having, in a position adjacent to the point of attachment to the azo linkage, either (a) a nitrogen atom in said ring of said nucleus which acts as a chelating site, or (b) a carbon atom in said ring of said nucleus having directly attached thereto a nitrogen atom which acts as a chelating site;
G is a metal chelating group, a salt thereof or a hydrolyzable precursor thereof;
said compound also containing a ballasted carrier moiety capable of releasing said diffusible azo dye as a function of development of said silver halide emulsion layer under alkaline conditions.

9 more elements

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 a releasable azo dye moiety, said compound having the following formula:

##STR62## wherein:
Z represents the atoms necessary to complete an aromatic carbocyclic or heterocyclic nucleus having at least one ring of 5 to 7 atoms;
Z' is an aromatic carbocyclic or heterocyclic nucleus having at least one ring of 5 to 7 atoms, said Z' having, in a position adjacent to the point of attachment to the azo linkage, either (a) a nitrogen atom in said ring of said nucleus which acts as a chelating site, or (b) a carbon atom in said ring of said nucleus having directly attached thereto a nitrogen atom which acts as a chelating site;
G is a metal chelating group, a salt thereof or a hydrolyzable precursor thereof;
said compound also containing a ballasted carrier moiety capable of releasing said diffusible azo dye as a function of development of said silver halide emulsion layer under alkaline conditions, 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 with metal ions, thereby forming a metal-complexed, azo dye transfer image.

7 more elements

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 a releasable azo dye moiety, said compound having the following formula:

##STR68## wherein:
Z represents the atoms necessary to complete an aromatic carbocyclic or heterocyclic nucleus having at least one ring of 5 to 7 atoms;
Z' is an aromatic carbocyclic or heterocyclic nucleus having at least one ring of 5 to 7 atoms, said Z' having, in a position adjacent to the point of attachment to the azo linkage, either (A) a nitrogen atom in said ring of said nucleus which acts as a chelating site, or (B) a carbon atom in said ring of said nucleus having directly attached thereto a nitrogen atom which acts as a chelating site;
G is a metal chelating group, a salt thereof or a hydrolyzable precursor thereof;
said compound also containing a ballasted carrier moiety capable of releasing said diffusible azo dye as a function of development of said silver halide emulsion layer under alkaline conditions, said ballasted carrier moiety being a group having the formula:
##STR69## 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 of 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 such 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.

26 more elements

Photographic products and processes employing nondiffusible azo dye-releasing compounds

Life of this patent

Photographic products and processes employing nondiffusible azo dye-releasing compounds

Life of this patent

Abstract

Claims67