# US 5,705,676 A · Chromogenic leuco redox-dye-releasing compounds for photothermographic elements

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- Number: US 5,705,676 A
- Document ID: US5705676A
- Status: Granted
- Kind: A
- Application number: 08/558,525
- Filed: 1995-11-16
- Granted: 1998-01-06
- Earliest claimed: 1994-06-30
- Assignees: Minnesota Mining and Manufacturing Company
- Inventors: Raffaella Biavasco; Lori S. Harring; Larry R. Krepski; Daniel E. Mickus; Mark B. Mizen; Sharon M. Simpson; Cristina Soncini; Kim M. Vogel
- Web page: https://patentgrep.com/patent/US5705676A

## CPC

- C07C 275/40: being further substituted by nitrogen atoms not being part of nitro or nitroso groups
- C07C 275/42: being further substituted by carboxyl groups
- C07C 311/46: Y being a hydrogen or a carbon atom
- G03C 1/49854: {Dyes or precursors of dyes (for diffusion-transfer G03C8/10, G03C8/4013)}
- Y10S 430/156: Precursor compound
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- 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)
- Y10S: TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS

## Abstract

A photothermographic element comprising a support bearing at least one heat-developable, photosensitive, image-forming photothermographic emulsion layer comprising: (a) a photosensitive silver halide; (b) a non-photosensitive, reducible source of silver; (c) a chromogenic leuco dye reducing agent; and (d) a binder; wherein the chromogenic leuco dye reducing agent is a chromogenic leuco redox-dye-releasing compound of the general formula: ##STR1## wherein: (i) Cp is a coupler group; (ii) N--D is a photographic developer group; and (iii) R.sup.1 is a --C(O)--NH--A--Dye group wherein Dye represents the chromophore of a thermally mobile dye; and A represents a single bond or a divalent linking group of the formula --X--R.sup.5 --L--, wherein R.sup.5 is a divalent hydrocarbon chain containing up to 12 carbon atoms, L is a single bond or a divalent group that binds the chromophore of the thermally mobile dye to R.sup.5, and X represents a single bond or an --SO.sub.2 -- group.

## Claims

### Claim 1

A chromogenic leuco redox-dye-releasing compound of the formula: ##STR31## wherein: (a) Cp is a coupler group;
(b) N--D is a photographic developer obtained from a primary amine color photographic developer group; and
(c) R.sup.1 is a --C(O)--NH--A--Dye group, wherein: Dye represents the chromophore of a thermally mobile dye; and A represents a single bond or a divalent linking group of the formula --X--R.sup.5 --L--, wherein R.sup.5 is a divalent hydrocarbon chain containing up to 12 carbon atoms, L is a single bond or a divalent group that binds the chromophore of the thermally mobile dye to R.sup.5, and X represents a single bond or an --SO.sub.2 -- group.

### Claim 2 (depends on 1)

The dye-releasing compound of claim 1 wherein R.sup.5 is a divalent aliphatic group containing 1-12 carbon atoms or a divalent aromatic group containing 5-12 carbon atoms.

### Claim 3 (depends on 2)

The dye-releasing compound of claim 2 wherein R.sup.5 is an alkylene group containing 1-8 carbon atoms.

### Claim 4 (depends on 1)

The dye-releasing compound of claim 1 wherein Cp is a photographic coupler group.

### Claim 5

A chromogenic leuco redox-dye-releasing compound of the general formula: ##STR32## wherein: (a) R is hydrogen or halogen;
(b) R.sup.1 is a --C(O)--NH--A--Dye group, wherein: Dye represents the chromophore of a thermally mobile dye; and A represents a single bond or a divalent linking group of the formula --X--R.sup.5 --L--, wherein R.sup.5 is a divalent hydrocarbon chain containing up to 12 carbon atoms, L is a single bond or a divalent group that binds the chromophore of the thermally mobile dye to R.sup.5, and X represents a single bond or an --SO.sub.2 -- group;
(c) R.sup.2 is a hydrogen atom, an alkoxy group, an alkyl group, or a ballasting group;
(d) R.sup.3 and R.sup.4 are each independently an aliphatic group, an aromatic group, or a --Z--Y group, wherein Z is an alkylene group containing 1-4 carbon atoms, and Y is a cyano group, a halogen atom, an alkoxy group containing 1-20 carbon atoms, or --OH; and
(e) Cp is a coupler group.

### Claim 6 (depends on 5)

The dye-releasing compound of claim 5 wherein Cp is a photographic coupler group.

### Claim 7 (depends on 5)

The dye-releasing compound of claim 5 wherein R.sup.2 is a hydrogen atom, an alkoxy group containing 1-20 carbon atoms, or an alkyl group containing 1-20 carbon atoms.

### Claim 8 (depends on 1)

The compound of claim 1 wherein N--D is a photographic developer group obtained from a primary aromatic amine color photographic developer.

### Claim 9 (depends on 4)

The compound of claim 4 wherein the coupler group contains a ballasting group.

### Claim 10 (depends on 1)

The compound of claim 1 wherein the developer group contains a ballasting group.

### Claim 11 (depends on 1)

The compound of claim 1 wherein Dye is the chromophore of an azo dye, azomethine dye, azamethine dye, anthraquinone dye, naphthoquinone dye, styryl dye, nitro dye, benzylidene dye, oxazine dye, diazine dye, thiazine dye, ketazine dye, imidazole dye, indoaniline dye, merocyanine dye, benzodifuranone dye, quinoline dye, indophenol dye, or a triphenylmethane dye.