# US 4,396,546 A · Photographic products and processes employing novel nondiffusible 6-(2-thienylazo)-3-pyridinol cyan dye-releasing compounds and precursors thereof

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- Number: US 4,396,546 A
- Document ID: US4396546A
- Status: Granted
- Kind: A
- Application number: 06/348,382
- Filed: 1982-02-12
- Granted: 1983-08-02
- Earliest claimed: 1981-04-29
- Assignees: Eastman Kodak Company
- Inventors: James J. Krutak; Robert J. Maleski; William H. Moore
- Web page: https://patentgrep.com/patent/US4396546A

## CPC

- G03C 8/10: of dyes or their precursors
- C09B 29/0059: {the heterocyclic ring containing only sulfur as heteroatom}
- G03C: PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES (for photomechanical purposes G03F); PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY (photographic processes characterised by the use or manipulation of apparatus classifiable per se in subclass G03B, see G03B; photomechanical production of textured or patterned surfaces G03F; electrophotography, magnetography G03G)
- C09B: ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES {, e.g. PIGMENTS}; MORDANTS; LAKES (fermentation or enzyme using processes to synthesise a desired chemical compound C12P)

## Abstract

Photographic elements, diffusion transfer assemblages and processes are described which employ a novel nondiffusible compound having a releasable 6-(2-thienylazo)-3-pyridinol cyan dye moiety or precursor thereof, the compound containing: (a) in the 3-position of the thienylazo moiety a carboxy group, a salt thereof or a hydrolyzable precursor thereof; and (b) a ballasted carrier moiety which is capable of releasing the diffusible 6-(2-thienylazo)-3-pyridinol dye moiety or precursor thereof under alkaline conditions.

## Claims

### Claim 1

A nondiffusible compound having a releasable 6-(2-thienylazo)-3-pyridinol cyan dye moiety or precursor thereof, said compound containing:
(a) in the 3-position of the thienylazo moiety a carboxy group, a salt thereof or a hydrolyzable precursor thereof; and
(b) a ballasted carrier moiety which is capable of releasing said diffusible azo dye as a function of development of a silver halide emulsion layer in an alkaline processing composition.

### Claim 2 (depends on 1)

The compound of claim 1 wherein said compound has the formula: ##STR33## wherein: (a) R.sup.1 is hydrogen, a hydrolyzable moiety or CAR;
(b) R.sup.2 is hydrogen, alkyl or substituted alkyl, such that COOR.sup.2 is a hydrolyzable moiety;
(c) CAR is a ballasted carrier moiety capable of releasing said diffusible 6-(2-thienylazo)-3-pyridinol dye moiety or precursor thereof as a function of development of said silver halide emulsion layer under alkaline conditions; and
(d) n is 0, 1 or 2, with the proviso that when n is 0, then R.sup.1 is CAR.

### Claim 3 (depends on 2)

The compound of claim 2 wherein R.sup.2 is hydrogen, phthalimidomethyl or cyanoethyl.

### Claim 4 (depends on 2)

The compound of claim 2 wherein R.sup.1 is hydrogen, R.sup.2 is hydrogen, and the pyridine ring has an amino group in the 2-position.

### Claim 5 (depends on 2)

The compound of claim 2 wherein the thienyl ring has in the 5-position an R.sup.3 CO group, wherein R.sup.3 is an alkyl or substituted alkyl group having from 1 to about 10 carbon atoms or an aryl or substituted aryl group having from 6 to about 10 carbon atoms.

### Claim 6 (depends on 2)

The compound of claim 2 wherein 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 oxidizable 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 dye.

### Claim 7 (depends on 6)

The compound of claim 6 wherein the Carrier moiety contains atoms according to the following configuration:
a(--C.dbd.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 (depends on 2)

The compound of claim 2 wherein CAR is a group having the formula: ##STR34## 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.sup.4 or NHR.sup.5 wherein R.sup.4 is hydrogen or a hydrolyzable moiety and R.sup.5 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; and
(d) j is a positive integer of 1 to 2 and is 2 when D is OR.sup.4 or when R.sup.5 is hydrogen or an alkyl group of less than 8 carbon atoms.

### Claim 9 (depends on 8)

The compound of claim 8 wherein D is OH, j is 2 and Y is a naphthalene nucleus.

### Claim 10 (depends on 2)

The compound of claim 2 wherein said CAR is capable of releasing said diffusible 6-(2-thienylazo)-3-pyridinol cyan dye moiety or precursor thereof as an inverse function of development of a silver halide emulsion layer under alkaline conditions.

### Claim 11 (depends on 10)

The compound of claim 10 wherein said CAR is a group having the formula: ##STR35## 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.sup.1 represents at least the atoms necessary to complete a quinone nucleus;
r is a positive integer of 1 or 2;
R.sup.6 is an alkyl radical having 1 to about 40 carbon atoms or an aryl radical having 6 to about 40 carbon atoms; and
k is a positive integer of 1 to 2 and is 2 when R.sup.6 is a radical of less than 8 carbon atoms.

### Claim 12 (depends on 10)

The compound of claim 10 wherein said CAR is a group having the formula: ##STR36## 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.sup.2 represents at least the atoms necessary to complete a benzene nucleus; and
R.sup.7 is an alkyl radical having 1 to about 4 carbon atoms.

### Claim 13 (depends on 10)

The compound of claim 10 wherein said CAR is a group having the formula: ##STR37## 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.sup.2 represents at least the atoms necessary to complete a benzene nucleus; and
R.sup.7 is an alkyl radical having 1 to about 4 carbon atoms.

### Claim 14 (depends on 10)

The compound of claim 10 wherein said CAR is a group having the formula: ##STR38## 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.sup.2 represents at least the atoms necessary to complete a benzene nucleus;
r is a positive integer of 1 or 2;
R.sup.6 is an alkyl radical having 1 to about 40 carbon atoms or an aryl radical having 6 to about 40 carbon atoms;
k is a positive integer of 1 to 2 and is 2 when R.sup.6 is a radical of less than 8 carbon atoms; and
K is OH or a hydrolyzable precursor thereof.

### Claim 15 (depends on 1)

The compound of claim 1 wherein said dye-releasing compound is: ##STR39##

### Claim 16 (depends on 1)

The compound of claim 1 wherein said dye-releasing compound is: ##STR40##

### Claim 17 (depends on 1)

The compound of claim 1 wherein said dye-releasing compound is: ##STR41##

### Claim 18 (depends on 1)

The compound of claim 1 wherein said dye-releasing compound is: ##STR42## wherein R.sup.8 is ##STR43##

### Claim 19 (depends on 1)

The compound of claim 1 wherein said dye-releasing compound is: ##STR44## wherein R.sup.9 is ##STR45##

### Claim 20 (depends on 1)

The compound of claim 1 wherein said dye-releasing compound is: ##STR46## wherein R.sup.10 is ##STR47##

### Claim 21 (depends on 1)

The compound of claim 1 wherein said dye-releasing compound is: ##STR48## wherein R.sup.11 is ##STR49##