US 4,148,643 A · Photographic products and processes employing nondiffusible azo dye-releasing compounds

Abstract

Photographic elements, diffusion transfer assemblages and processes are described which employ a novel nondiffusible compound having a releasable azo dye moiety. The compound has the formula: ##STR1## wherein: G is a metal chelating group (or a salt or hydrolyzable precursor thereof) or a group which together with a ##STR2## IS CAR (bonded through the oxygen); G.sup.1 is a hydroxy group (or a salt of hydrolyzable precursor thereof); Z is an electron withdrawing group; Z' is alkyl, aryl or N(R).sub.2 (R being H, alkyl or aryl); Car is a ballasted carrier moiety; and T is 0 or 1. The dye can be transferred imagewise to an image-receiving layer where it can be contacted with metal ions to form a metal-complexed azo dye transfer image of excellent stability. The retained dye image in the photographic element can also be bleached, fixed and metallized to form a color transparency or a motion picture film.

Claims35

Dependent claims

In a photographic element comprising a support having thereon at least one photosensitive silver halide emulsion layer, said emulsion layer having associated therewith a nondiffusible dye-releasing compound, the improvement wherein said nondiffusible dye-releasing compound has 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## is CAR, said CAR being bonded to the benzene ring through the oxygen of said ##STR29## G.sup.1 is a hydroxy group, a salt thereof, or a hydrolyzable precursor thereof;
Z is an electron withdrawing group having the formula --CON(R).sub.2, --SO.sub.2 N(R).sub.2, --COOR, --CN, SO.sub.2 R' or --COR', wherein R' is an alkyl group of 1 to 8 carbon atoms or an aryl group of 6 to 10 carbon atoms, and each R is H or R';
Z' is an alkyl group of 1 to 8 carbon atoms, an aryl group of 6 to 10 carbon atoms or N(R).sub.2 ;
Car represents 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;
and
t is an integer of 0 or 1, with the proviso that the compound contains at least one but not more than two CAR groups.

5 more elements

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 diffusible azo dye moiety, said compound having the formula:
##STR38## wherein:
G is a metal chelating group, a salt thereof or a hydrolyzable precursor thereof;
or a group which together with a ##STR39## is CAR, said CAR being bonded to the benzene ring through the oxygen of said ##STR40## G.sup.1 is a hydroxy group, a salt thereof, or a hydrolyzable precursor thereof;
Z is an electron withdrawing group having the formula --CON(R).sub.2, --SO.sub.2 N(R).sub.2, --COOR, --CN, SO.sub.2 R' or COR', wherein R' is an alkyl group of 1 to 8 carbon atoms or an aryl group of 6 to 10 carbon atoms, and each R is H or R';
Z' is an alkyl group of 1 to 8 carbon atoms, an aryl group of 6 to 10 carbon atoms or N(R).sub.2 ;
Car represents 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;
and
t is an integer of 0 or 1, with the proviso that the compound contains at least one but not more than two CAR groups.

10 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 at least one of said ballasted dye releasers is a nondiffusible compound having at least one diffusible azo dye moiety, said compound having the formula:
##STR41## wherein:
G is a metal chelating group, a salt thereof or a hydrolyzable precursor thereof;
or a group which together with a ##STR42## is CAR, said CAR being bonded to the benzene ring through the oxygen of said ##STR43## G.sup.1 is a hydroxy group, a salt thereof, or a hydrolyzable precursor thereof;
Z is an electron withdrawing group having the formula --CON(R).sub.2, --SO.sub.2 N(R).sub.2, --COOR, --CN, SO.sub.2 R' or --COR', wherein R' is an alkyl group of 1 to 8 carbon atoms or an aryl group of 6 to 10 carbon atoms, and each R is H or R';
Z' is an alkyl group of 1 to 8 carbon atoms, an aryl group of 6 to 10 carbon atoms or N(R).sub.2 ;
Car represents a ballasted carrier moiety which is capable of releasing said diffusable azo dye as a function of development of said silver halide emulsion layer under alkaline conditions;
and
t is an integer of 0 or 1, with the proviso that the compound contains at least one but not more than two CAR groups.

12 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 dye-releasing compound having at least one diffusible azo dye moiety, said compound having the formula:

##STR44## wherein:
G is a metal chelating group, a salt thereof or a hydrolyzable precursor thereof;
or a group which together with a ##STR45## is CAR, said CAR being bonded to the benzene ring through the oxygen of said ##STR46## G.sup.1 is a hydroxy group, a salt thereof, or a hydrolyzable precursor thereof;
Z is an electron withdrawing group having the formula --CON(R).sub.2, --SO.sub.2 N(R).sub.2, --COOR, --CN, SO.sub.2 R' or --COR', wherein R' is an alkyl group of 1 to 8 carbon atoms or an aryl group of 6 to 10 carbon atoms, and each R is H or R';
Z' is an alkyl group of 1 to 8 carbon atoms, an aryl group of 6 to 10 carbon atoms, or N(R).sub.2 ;
Car represents 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;
and
t is an integer of 0 or 1, with the proviso that the compound contains at least one but not more than two CAR groups;
said process comprising:
(1) treating said 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.

11 more elements

##STR47## wherein:
G is a metal chelating group, a salt thereof or a hydrolyzable precursor thereof;
or a group which together with a ##STR48## is CAR, said CAR being bonded to the benzene ring through the oxygen of said ##STR49## G.sup.1 is a hydroxy group, a salt thereof, or a hydrolyzable precursor thereof;
Z is an electron withdrawing group having the formula --CON(R).sub.2, --SO.sub.2 N(R).sub.2, --COOR, --CN, SO.sub.2 R' or --COR', wherein R' is an alkyl group of 1 to 8 carbon atoms or an aryl group of 6 to 10 carbon atoms, and each R is H or R';
Z' is an alkyl group of 1 to 8 carbon atoms, an aryl group of 6 to 10 carbon atoms or N(R).sub.2 ;
t is an integer of 0 or 1, with the proviso that the compound contains at least one but not more than two CAR groups;
and
Car represents 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 ballasted carrier moiety being a group having the formula:
##STR50## 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 NHR.sup.3 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 to 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.

30 more elements

Dependencies are inferred from the claim text.

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

Claims35