# US 5,344,749 A · Filter dyes for rapid processing applications

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- Number: US 5,344,749 A
- Document ID: US5344749A
- Status: Granted
- Kind: A
- Application number: 08/118,738
- Filed: 1993-09-10
- Granted: 1994-09-06
- Earliest claimed: 1992-09-11
- Assignees: AGFA-Gevaert, N.R.
- Inventors: Eric Kiekens; Paul Callant
- Web page: https://patentgrep.com/patent/US5344749A

## CPC

- G03C 1/832: {Methine or polymethine dyes}
- C09B 23/005: {the substituent being a COOH and/or a functional derivative thereof}
- C09B 23/0091: {having only one heterocyclic ring at one end of the methine chain, e.g. hemicyamines, hemioxonol (styryl dyes see C09B23/14)}
- Y10S 430/159: Development dye releaser, DDR
- Y10S 430/164: Rapid access processing
- Y10S 430/167: X-ray
- 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)
- Y10S: TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS

## Abstract

The synthesis and the application of new dyes is described, said new dyes being incorporated in non-migratory state in hydrophilic colloid layers of photographic materials wherefrom they can be rapidly removed after being quickly decolorized in alkaline aqueous liquids used in the processing of said materials. The filter dyes have an amide function or a derivative therefrom as a substituent at the mono- or trimethine chain.

## Claims

### Claim 1

A photographic material comprising a support and at least one light-sensitive silver halide emulsion layer characterized in that it comprises in a hydrophilic colloid layer at least one filter dye corresponding to the following general formula (I): ##STR8## wherein n represents 0 or 1;
p represents 0, 1 or 2;
Q represents the atoms necessary to form an acidic nucleus
R.sub.1 represents hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, COOR.sub.2,NHCOR.sub.3 or NHSO.sub.2 R.sub.4 with R.sub.2 representing hydrogen or substituted or unsubstituted alkyl, R.sub.3 and R.sub.4 representing substituted or unsubstituted alkyl, or substituted or unsubstituted aryl,
X represents OR.sub.5, SR.sub.5 or NR.sub.6 R.sub.7, wherein
R.sub.5 represents H, substituted or unsubstituted alkyl, substituted or unsubstituted aryl and
each of R.sub.6 and R.sub.7 which may be the same or different represents hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted aryl or the necessary atoms, to form a ring together with the N-atom to which they are attached and the C-atom of the phenylene ring in ortho position with respect to said N-atom; R.sub.6 and R.sub.7 together represent the necessary atoms to form a ring with the N-atom to which they are attached; L.sub.1, L.sub.2, L.sub.3 represent substituted or unsubstituted methine with the proviso that at least one of L.sub.1, L.sub.2 or L.sub.3 must be substituted by --CONR.sub.8 R.sub.9 ;
R.sub.8 and R.sub.9 which may be the same or different represent hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, NH.sub.2, NHR.sub.10, NR.sub.11 R.sub.12 with R.sub.10, R.sub.11 and R.sub.12 representing a substituted or unsubstituted alkyl, or a substituted or unsubstituted aryl and wherein at least one of R.sub.1 to R.sub.12 contains an ionizable group.

### Claim 2 (depends on 1)

A photographic material according to claim 1 wherein said at least one dye is a filter dye corresponding to the following general formula (II): ##STR9## wherein each of n, p, X, R.sub.1, L.sub.1, L.sub.2 and L.sub.3 has one of the meanings given in claim 1 and wherein
R.sub.13 represents hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, or sulfolanyl,
R.sub.14 represents hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted aryl,COOR.sub.2, NHCOR.sub.3, NHSO.sub.2 R.sub.4, with R.sub.2, R.sub.3 and R.sub.4 representing hydrogen, substituted or unsubstituted alkyl, or substituted or unsubstituted aryl, and wherein at least one of R.sub.1 to R.sub.14 contains an alkali-soluble group.

### Claim 3 (depends on 1)

A photographic material according to claim 1 wherein said at least one filter dye is incorporated into an antihalation undercoat layer coated between the support and at least one silver halide emulsion layer.

### Claim 4 (depends on 1)

A photographic material according to claim 1 wherein said at least one filter dye is incorporated into a backing layer.

### Claim 5 (depends on 1)

A photographic material according to claim 1 wherein the dye(s) is(are) present in a hydrophilic colloid layer in an amount of 0.01 to 1.0 mmole/m.sup.2.

### Claim 6 (depends on 1)

A photographic material according to claim 1 wherein the filter dye(s) is(are) present as a gelatinous dispersion(s).

### Claim 7 (depends on 1)

A photographic material according to claims 1 wherein the filter dye(s) is(are) present as solid silica particle dispersion(s).

### Claim 8 (depends on 1)

A photographic material according to claim 1 wherein said photographic material is an X-ray material.

### Claim 9 (depends on 8)

Use of a photographic material according to claim 8 for rapid processing applications shorter than 60 seconds, comprising imagewise exposure of the material followed by post exposure processing comprising developing, fixing, rinsing and drying steps.

### Claim 10 (depends on 1)

A photographic material according to claim 1 wherein in the general formula (I) the said acidic nucleus represents a pyrazolone, barbituric acid, thiobarbituric acid, rhodanine, hydantoine, oxazolidindione, thio-oxazolidindione or isoxazolinone nucleus.