# US 5,348,847 A · Silver halide color photographic material

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- Number: US 5,348,847 A
- Document ID: US5348847A
- Status: Granted
- Kind: A
- Application number: 07/982,445
- Filed: 1992-11-27
- Granted: 1994-09-20
- Earliest claimed: 1991-11-27
- Assignees: Fuji Photo Film Co., Ltd.
- Inventors: Makoto Suzuki; Osamu Takahashi; Yasuhiro Shimada; Koushin Matsuoka; Yasuhiro Yoshioka
- Web page: https://patentgrep.com/patent/US5348847A

## CPC

- C07D 487/04: Ortho-condensed systems
- C09B 55/009: {Azomethine dyes, the C-atom of the group -C=N- being part of a ring (Image)}
- G03C 7/383: {three nitrogen atoms}
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- 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)
- 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)

## Abstract

Disclosed is a silver halide color photographic material comprising a support having thereon at least one layer containing one or more cyan couplers of formula (I): ##STR1## wherein R.sub.11 represents a branched or cyclic alkyl group, a branched or cyclic alkoxy group, a substituted aryl group, or a substituted aryloxy group; R.sub.21 represents a substituent which may optionally be substituted. R.sub.12 represents an aliphatic group, an aryl group, a heterocyclic group, an alkoxy group, an aryloxy group, an alkylamino group, an anilino group, a heterocyclic-oxy group, or a heterocyclic-amino group; R.sub.22 and R.sub.32 each represents a substituent; r.sub.2 represents an integer of from 0 to 4; provided that when r.sub.2 is a plural number, the plurality of R.sub.32 groups may be the same or different; R.sub.13, R.sub.23 and R.sub.33 each represent a hydrogen atom or a substituent; provided that the total of Taft's substituent constant .sigma.* values of R.sub.13, R.sub.23 and R.sub.33 is 1.5 or more; R.sub.43 represents a substituent. In formulae (I), (II) and (III), X.sub.1, X.sub.2 and X.sub.3 each represents a hydrogen atom, or a group which is capable of splitting off from the formula by a coupling reaction with an oxidation product of an aromatic primary amine color developing agent; and the group of R.sub.11, R.sub.21 or X.sub.1, the group of R.sub.12, R.sub.22, R.sub.32 or X.sub.2, or the group of R.sub.13, R.sub.23, R.sub.33, R.sub.43 or X.sub.3 may be a divalent group to form a dimer or a higher polymer or to bond to a polymer chain to form a homopolymer or a copolymer. The material forms a color image with good color hue and color fastness. It is hardly fogged, and the dyes formed from the couplers hardly associate with each other in the material.

## Claims

### Claim 1

A silver halide color photographic material, comprising a support having thereon at least one red-sensitive silver halide emulsion layer containing at least one cyan coupler of the following general formula (I): ##STR52## wherein R.sub.11 represents a branched or cyclic alkyl group, a branched or cyclic alkoxy group, a substituted aryl group, or a substituted aryloxy group;
R.sub.21 represents a substituent;
X.sub.1 represents a hydrogen atom or a group which is capable of splitting off from the formula by a coupling reaction with an oxidation product of an aromatic primary amine color developing agent; and
a group represented by R.sub.11, R.sub.21 or X.sub.1 may be divalent and form a dimer or a higher polymer or bond to a polymer chain to form a homopolymer of copolymer.

### Claim 2 (depends on 1)

The silver halide color photographic material as claimed in claim 1, wherein the substituted aryl group in R.sub.11 formula (I) is represented by formula (IV) and the substituted aryloxy group in R.sub.11 of formula (I) is represented by formula (V); ##STR53## wherein R.sub.31 and R.sub.41 may be same or different and each represents a substituent; and
r.sub.1 represents an integer of from 0 to 4, and when r.sub.1 is a plural number, the plurality of R.sub.41 groups may be the same or different.

### Claim 3 (depends on 2)

The silver halide color photographic material as claimed in claim 2, wherein R.sub.31 and R.sub.41 each represents a halogen atom, an aliphatic group, an aryl group, a heterocyclic group, an alkoxy group, an aryloxy group, a heterocyclic oxy group, a heterocyclic thio group, an acyloxy group, a silyloxy group, an alkyl- or arylsulfamoyloxy group, an acylamino group, an alkylamino group, an arylamino group, a ureido group, a sulfamoylamino group, an alkenyloxy group, a formyl group, an alkyl-, aryl- or heterocyclic acyl group, an alkyl-, aryl-, or heterocyclic sulfonyl group, a sulfinyl group, an alkyl-, aryl- or heterocyclic oxycarbonyl group, an alkyl-, aryl- or heterocyclic oxycarbonylamino group, a sulfonamido group, a carbamoyl group, a sulfamoyl group, a phosphonyl group, an imido group, an azolyl group, a hydroxyl group, a cyano group, a carboxyl group, a nitro group, a sulfo group, or an unsubstituted amino group.

### Claim 4 (depends on 1)

The silver halide color photographic material as claimed in claim 1, wherein R.sub.11 in formula (I) represents a branched or cyclic alkoxy group or a substituted aryloxy group.

### Claim 5 (depends on 4)

The silver halide color photographic material as claimed in claim 4, wherein R.sub.11 represents a branched or cyclic alkoxy group.

### Claim 6 (depends on 4)

The silver halide color photographic material as claimed in claim 4, wherein R.sub.11 represents a branched alkoxy group.

### Claim 7 (depends on 1)

The silver halide color photographic material as claimed in claim 1, wherein R.sub.21 represents a halogen atom, an alkyl group, an aryl group, a heterocyclic group, an alkoxy group, an aryloxy group, a heterocyclic oxy group, an acyloxy group, an acylamino group, an alkylamino group, an anilino group, a ureido group, a sulfamoylamino group, an alkenyloxy group, an alkyl-, aryl- or heterocyclic acyl group, an alkyl-, aryl-, or heterocyclic sulfonyl group, a sulfinyl group, an alkyl-, aryl- or heterocyclic oxycarbonyl group, an alkyl-, aryl- or heterocyclic oxycarbonylamino group, a sulfonamido group, a carbamoyl group, a sulfamoyl group, an imido group, a hydroxyl group, a cyano group, a carboxyl group, a nitro group, or a sulfo group.

### Claim 8 (depends on 7)

The silver halide color photographic material as claimed in claim 7, wherein R.sub.21 represents an alkyl group, an aryl group, a carbamoyl group, an acylamino group, or a ureido group.

### Claim 9 (depends on 8)

The silver halide color photographic material as claimed in claim 8, wherein R.sub.21 represents an aryl group.

### Claim 10 (depends on 1)

The silver halide color photographic material as claimed in claim 1, wherein X.sub.1 represents a hydrogen atom, a halogen atom, an alkoxy group, an aryloxy group, an acyloxy group, an alkyl- or arylsulfonyloxy group, an acylamino group, an alkyl- or arylsulfonamido group, an alkoxycaronyloxy group, an aryloxycaronyloxy group, an alkyl-, aryl- or heterocyclic thio group, a carbamoylamino group, a 5- or 6-membered heterocyclic group, an imido group, or an arylazo group.

### Claim 11 (depends on 1)

The silver halide color photographic material as claimed in claim 1, wherein the cyan coupler of formula (I) is contained in an amount of from 1.times.10.sup.-3 mol to 1 mol/mol of silver halide.

### Claim 12

A silver halide color photographic material, comprising a support having thereon at least one red-sensitive silver halide emulsion layer containing at least one cyan coupler of the following general formula (II): ##STR54## wherein R.sub.12 represents an aliphatic group, an aryl group, a heterocyclic group, an alkoxy group, an aryloxy group, an alkylamino group, an anilino group, a heterocyclic oxy group, or a heterocyclic amino group;
R.sub.22 and R.sub.32 each represents a substituent;
r.sub.2 represent an integer of from 0 to 4; provided that when r.sub.2 is a plural number, the plurality of R.sub.32 groups may be the same or different;
X.sub.2 represents a hydrogen atom or a group which is capable of splitting off from the formula by a coupling reaction with an oxidation product of an aromatic primary amine color developing agent; and a group represented by R.sub.12, R.sub.22, R.sub.32 or X.sub.2, may be divalent and form a dimer or a higher polymer or bond to a polymer chain to form a homopolymer of copolymer.

### Claim 13 (depends on 12)

The silver halide color photographic material as claimed in claim 12, wherein R.sub.22 and R.sub.32 each represents a halogen atom, an alkyl group, an aryl group, a heterocyclic group, an alkoxy group, an aryloxy group, a heterocyclic oxy group, a heterocyclic thio group, an acyloxy group, a silyloxy group, an acylamino group, an alkylamino group, an anilino group, a ureido group, a sulfamoylamino group, a sulfinyl group, an alkyl- or aryl oxycarbonyl group, an alkyl- or aryl- oxycarbonylamino group, a sulfonamido group, a carbamoyl group, a sulfamoyl group, a phosphonyl group, an imido group, an azolyl group, a hydroxyl group, a cyano group, a carboxyl group, a nitro group, or a sulfo group.

### Claim 14 (depends on 12)

The silver halide color photographic material as claimed in claim 12, wherein R.sub.12 represents an alkoxy group, an aryloxy group, an alkylamino group, or an anilino group.

### Claim 15 (depends on 14)

The silver halide color photographic material as claimed in claim 14, wherein R.sub.12 represents a branched or cyclic alkoxy group or a substituted aryloxy group.

### Claim 16 (depends on 12)

The silver halide color photographic material as claimed in claim 12, wherein R.sub.22 represents an alkyl group, an alkoxy group, an acylamino group, a sulfonamido group, a halogen atom, a ureido group, an alkylamino group, an anilino group or a carbamoyl group.

### Claim 17 (depends on 12)

The silver halide color photographic material as claimed in claim 12, wherein X.sub.2 represents a hydrogen atom, a halogen atom, an alkoxy group, an aryloxy group, an acyloxy group, an alkyl- or arylsulfonyloxy group, an acylamino group, an alkyl- or arylsulfonamido group, an alkoxycarbonyloxy group, an aryloxycarbonyloxy group, an alkyl-, aryl- or heterocyclic thio group, a carbamoylamino group, a 5- or 6-membered heterocyclic group, an imido group, or an arylazo group.

### Claim 18 (depends on 12)

The silver halide color photographic material as claimed in claim 12, wherein the cyan coupler of formula (II) is contained in an amount of from 1.times.10.sup.-3 mol to 1 mol/mol of silver halide.