# US 5,352,573 A · Silver halide color photographic light-sensitive material

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- Number: US 5,352,573 A
- Document ID: US5352573A
- Status: Granted
- Kind: A
- Application number: 07/982,439
- Filed: 1992-11-27
- Granted: 1994-10-04
- Earliest claimed: 1991-11-27
- Assignees: Fuji Photo Film Co., Ltd.
- Inventors: Nobuo Seto; Yasuhiro Yoshioka; Makoto Suzuki; Masakazu Morigaki
- Web page: https://patentgrep.com/patent/US5352573A

## CPC

- G03C 7/301: {Combinations of couplers having the coupling site in pyrazoloazole rings and photographic additives}
- 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

A silver halide color photographic light-sensitive material having an improved color forming property, color reproducibility and image preservative performance is described. The light-sensitive material comprises a support having provided thereon at least one silver halide emulsion layer comprising (a) a cyan dye-forming coupler represented by the following formulas (I) or (II): ##STR1## wherein Za, Zb, R.sub.1, R.sub.2 and X represent substituents described herein; (b) a compound represented by the following formula (A): ##STR2## wherein R.sub.a1 -R.sub.a6 represent substituents described herein.

## Claims

### Claim 1

A silver halide color photographic light-sensitive material comprising a support having provided thereon at least one red-sensitive silver halide emulsion layer comprising (a) a cyan dye-forming coupler represented by the following formulas (I-a) or (II-a): ##STR55## wherein R.sub.1 and R.sub.2 each are an electron attractive group having a Hammett's substituent constant .sigma..sub.p of 0.20 or more and the sum of the .sigma..sub.p values of R.sub.1 and R.sub.2 is 0.65 or more;
R.sub.3 represents a hydrogen atom or a substituent;
X represents a hydrogen atom or a group capable of splitting off upon a reaction with an oxidation product of an aromatic primary amine color developing agent; and
the group represented by R.sub.1, R.sub.2, R.sub.3 or X may become a divalent group and combine with a monomer higher than a dimer and a high molecular weight chain to form a homopolymer or a copolymer; and
(b) a compound represented by the following formula (A): ##STR56## wherein R.sub.a1 represents an aliphatic group, an aromatic group, a heterocyclic group, --Si(R.sub.a7) (R.sub.a8 (R.sub.a9), --CO(R.sub.a10), --SO.sub.2 (R.sub.a11), or --P(O).sub.n (R.sub.a12) (R.sub.a13);
R.sub.a2, R.sub.a3, R.sub.a4, R.sub.a5 and R.sub.a6 may be the same or different and each represent a hydrogen atom, --X'--R.sub.a1, an aliphatic group, an aromatic group, a heterocyclic group, an aliphatic oxycarbonyl group, an aromatic oxycarbonyl group, a halogen atom, an acyl group, a sulfonyl group, a carbamoyl group, a sulfamoyl group, a cyano group, a nitro group, a sulfo group, or a carboxyl group;
--X--represents --O-- or --N(R.sub.a1 ')--;
--X'-- represents --O--, --S-- or --N(R.sub.a1)--;
R.sub.a7, R.sub.a8 and R.sub.a9 may be the same or different and each represent an aliphatic group, an aromatic group, an aliphatic oxy group, or an aromatic oxy group;
R.sub.a10 and R.sub.a11 each represent an aliphatic group, an aromatic group, an aliphatic amino group, or an aromatic amino group;
R.sub.a12 and R.sub.a13 may be the same or different and each represent an aliphatic group, an aromatic group, an aliphatic oxy group, or an aromatic oxy group;
n represents 0 or 1; and
R.sub.a1 ' represents a hydrogen atom or a group defined for R.sub.a1 ; of the respective groups of --X--R.sub.a1 and R.sub.a2 to R.sub.a6, the groups located in an ortho position to each other may be combined to form a 5 to 8-membered ring;
and where --X-- or --X'-- is --N(R.sub.a1 ')--, R.sub.a1 and R.sub.a1 ' may be combined with each together to form a 5 to 8- membered ring.

### Claim 2 (depends on 1)

The silver halide color photographic light-sensitive material as in claim 1, wherein R.sub.3 is an alkyl group, an aryl group, a heterocyclic group, a cyano group, a nitro group, an acylamino group, an anilino group, a ureido group, a sulfamoylamino group, an alkylthio group, an arylthio group, an alkoxycarbonylamino group, a sulfonamido group, a carbamoyl group, a sulfamoyl group, a sulfonyl group, an alkoxycarbonyl group, a heterocyclicoxy group, an acyloxy group, a carbamoyloxy group, an aryloxycarbonylamino group, an imido group, a heterocyclic thio group, a sulfinyl group, a phosphonyl group, an aryloxycarbonyl group, an acyl group, or an azolyl group.

### Claim 3 (depends on 2)

The silver halide color photographic light-sensitive material as in claim 2, wherein R.sub.3 is an alkyl group or an aryl group.

### Claim 4 (depends on 1)

The silver halide color photographic light-sensitive material as in claim 1, wherein R.sub.1 and R.sub.2 each are an acyl group, an acyloxy group, a carbamoyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, a cyano group, a nitro group, a dialkylphosphono group, a diarylphosphono group, a diarylphosphinyl group, an alkyl-sulfinyl group, an arylsulfinyl group, an alkylsulfonyl group, an arylsulfonyl group, a sulfonyloxy group, an acylthio group, a sulfamoyl group, a thiocyanato group, a thiocarbonyl group, a halogenated alkyl group, a halogenated alkoxy group, a halogenated aryloxy group, a halogenated alkylamino group, a halogenated alkylthio group, an aryl group substituted with the other electron attractive group having .sigma..sub.p of 0.20 or more, a heterocyclic group, a halogen atom, an azo group, or a selenocyanato group and the sum of the .sigma..sub.p values of R.sub.l and R.sub.z is 0.65 or more.

### Claim 5 (depends on 4)

The silver halide color photographic light-sensitive material as in claim 4, wherein R.sub.1 and R2 each are an acyl group, an acyloxy group, a carbamoyl group, an alkoxycarbonyl group, an aryloxy-carbonyl group, a cyano group, a nitro group, an alkylsulfinyl group, an arylsulfinyl group, an alkyl-sulfonyl group, an arylsulfonyl group, a sulfamoyl group, a halogenated alkyl group, a halogenated alkoxy group, a halogenated alkylthio group, a halogenated aryloxy group, an aryl group substituted with the other electron attractive group having .sigma..sub.p of 0.20 or more, or a heterocyclic group and the sum of the .sigma..sub.p values of R.sub.1 and R.sub.2 is 0.65 or more.

### Claim 6 (depends on 5)

The silver halide color photographic light-sensitive material as in claim 5, wherein R.sub.1 and R.sub.2 each are an alkoxycarbonyl group, a nitro group, a cyano group, an arylsulfonyl group, a carbamoyl group, or a halogenated alkyl group and the sum of the .sigma..sub.p values of R.sub.1 and R.sub.2 is 0.65 or more.

### Claim 7 (depends on 1)

The silver halide color photographic light-sensitive material as in claim 1, wherein X in formula (I-a) and (II-a) is 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 carbamoylaminio group, a 5-membered or 6-membered nitrogen-containing heterocyclic group, an imido group, or an arylazo group.

### Claim 8 (depends on 7)

The silver halide color photographic light-sensitive material as in claim 7, wherein X in formula (I-a) and (II-a) is a halogen atom, an alkoxy group, an aryloxy group, an alkyl or arylthio group, or a 5-membered or 6-membered nitrogen-containing heterocyclic group bonded to a coupling active site via the nitrogen atom.

### Claim 9 (depends on 8)

The silver halide color photographic light-sensitive material as in claim 8, wherein X in formula (I-a) and (II-a) is a halogen atom, or an alkyl or alkylthio group.

### Claim 10 (depends on 1)

The silver halide color photographic light-sensitive material as in claim 1, wherein in formula (A), at least one of R.sub.a2 to R.sub.a6 is --X'--R.sub.a1.

### Claim 11 (depends on 1)

The silver halide color photographic light-sensitive material as in claim 1, wherein in formula (A), --X-- is --O-- and R.sub.a1 is --P(O) (R.sub.a12) (R.sub.a13).

### Claim 12 (depends on 1)

The silver halide color photographic light-sensitive material as in claim 1, wherein the amount of formula (A) in the material is 0.5 to 300 mole per mole of said cyan dye-forming coupler in the material.

### Claim 13 (depends on 1)

The silver halide color photographic light-sensitive material as in claim 1, wherein said cyan dye-forming coupler is represented by the formula (I-a).

### Claim 14 (depends on 1)

The silver halide color photographic light-sensitive material as in claim 1, wherein R.sub.1 is a cyano group and R.sub.2 is a branched alkoxycarbonyl group.

### Claim 15 (depends on 1)

The silver halide color photographic light-sensitive material as in claim 1, wherein said compound of formula (A) is represented by the following formulas (A-I) to (A-XVII): ##STR57## wherein R.sub.a1 to R.sub.a6 and R.sub.a1 ' each has the same meanings as defined for formula (A);
R.sub.51 to R.sub.69 may be the same or different and each represent a hydrogen atom, an alkyl group, or an aryl group;
R.sub.54 and R.sub.55 and R.sub.55 and R.sub.56 may be combined with each other to form a 5 to 7-membered hydrocarbon ring;
B and D each represent a single bond, --C(R.sub.70)(R.sub.71)-- or --O-- and E represents a single bond or --C(R.sub.70)(R.sub.71)--, wherein R.sub.70 and R.sub.71 may be the same or different and each represent a hydrogen atom, an alkyl group, or an aryl group;
R.sub.b1 represents an aliphatic group, or an aromatic group;
X.sub.b1 represents a single bond, a substituted or unsubstituted methylene group, --S--, --O--, --CO--, --N(R.sub.a1 ')--, or --SO.sub.2 --; and
m.sub.1 to m.sub.5 each represent 0 or 1.

### Claim 16 (depends on 15)

The silver halide color photographic light-sensitive material as in claim 15, wherein said compound of formula (A) is represented by the formulas (A-I), (A-V), (A-VI), (A-VII), (A-VIII), (A-IX), (A-X), (A-XI), (A-XIV) or (A-XVI).

### Claim 17 (depends on 1)

The silver halide color photographic light-sensitive material as in claim 1, wherein the content of said cyan dye-forming coupler is 1.times.10.sup.-3 to 1 mole per mole of silver halide.