Silver halide color photographic material

A silver halide color photographic material excellent in color reproducibility, color forming property, color image fastness and processing dependency. The material comprises a yellow color forming silver halide emulsion layer formed on a support, said layer containing at least one yellow color forming coupler represented by general formula (I) dispersed by dissolution in a high boiling organic solvent in a weight ratio of the high boiling organic solvent to the yellow color forming coupler of 0.6 or more: ##STR1## wherein X represents an organic residue necessary for forming a nitrogen-containing heterocycle with a nitrogen atom; Y represents an aromatic group or a heterocyclic group; Z represents a group which is eliminatable by reaction of the coupler represented by general formula (I) with an oxidation product of a developing agent.

FIELD OF THE INVENTION 
The present invention relates to a silver halide color photographic 
material, and particularly to a silver halide color photographic material 
containing a novel yellow color forming coupler (hereinafter referred to 
as a yellow coupler). The material can provide improved color 
reproducibility, color image fastness to light and heat, and processing 
dependency. 
BACKGROUND OF THE INVENTION 
Silver halide color photographic materials are subjected to color 
development after exposure, which allows dye forming couplers to react 
with oxidation products of aromatic primary amine developing agents and 
form color images. 
In this method, the color images are generally reproduced by the 
subtractive color process. In this process, couplers for forming yellow, 
magenta and cyan dyes are used which are dispersed in silver halide 
emulsion layers different in color sensitivity. Of these couplers, 
acylacetanilide-type couplers such as pivaloyl-type yellow couplers, and 
benzoyl-type yellow couplers and malondianilide-type couplers are widely 
known as the yellow couplers. 
The pivaloyl-type yellow couplers can provide excellent hue and color image 
fastness, and have been used mainly in color print materials. However, 
they exhibit the disadvantage of low molecular extinction coefficients and 
low coupling activities. Also with respect to hue and color image 
fastness, further developments have been desired to meet recently higher 
demands. 
The benzoyl-type yellow couplers have been used mainly in negative films 
for shooting, because of their high molecular extinction coefficients and 
high activities. However, they are broad in their absorption wave forms 
and provide low fastness of formed dye images, such that further 
developments have also been desired. 
The malondianilide-type yellow couplers are described, for example, in U.S. 
Pat. Nos. 4,149,886, 4,095,984 and 4,477,563. They are inferior to the 
above-described benzoyl-type couplers in hue and image fastness. 
Therefore, they are only used as couplers of the development inhibitor 
releasing-type and have limited applications. 
Couplers in which the disadvantages of the malondianilide-type couplers 
have been improved are described in European Patent 447020A1. However, 
even those couplers have not reached a fully satisfactory level in all of 
the color forming properties, hue and color image fastness. 
There is a strong desire to develop couplers having a satisfactory 
combination of high molecular extinction coefficient, high color forming 
properties, excellent hue and the excellent color image fastness. 
Various uses of high boiling organic solvents, antifading agents and color 
forming accelerators have been studied to compensate for the disadvantages 
of the yellow couplers of the types described above. For example, methods 
for improving the hue by use of high boiling organic solvents are 
described in JP-A-63-241547 (the term "JP-A" as used herein means an 
"unexamined published Japanese patent application") and JP-A-63-256952, 
and methods for improving color image fastness are described in U.S. Pat. 
No. 4,745,049, JP-A-64-11262, JP-A-64-17056, JP-A-64-10247, JP-A-64-50048 
and JP-A-2-4239. Methods for improving color image fastness by use of 
antifading agents are described, for example, in JP-A-61-2151, 
JP-A-61-6652, JP-A-1-196049 and JP-A-1-284853. Further, methods using 
water-insoluble, organic solvent-soluble polymers to improve the color 
image fastness are described in JP-A-64-50049. 
However, materials or methods which can fully meet increasingly heightened 
demands have not yet been reached, even by the above-described methods. 
Further improvements in couplers, or techniques for use thereof, are still 
strongly desired. 
SUMMARY OF THE INVENTION 
Therefore, an object of the present invention is to develop a novel yellow 
coupler having a combination of a high molecular extinction coefficient, 
high color forming properties, excellent hue and excellent color image 
fastness, and to provide a silver halide color photographic material which 
provides excellent color reproducibility, color image fastness and 
processing dependency using that coupler. 
The above-described object of the present invention can be obtained by the 
silver halide color photographic materials described below. In a first 
embodiment there is provided a silver halide color photographic material 
comprising a yellow color forming silver halide emulsion layer formed on a 
support, said layer containing at least one yellow color forming coupler 
represented by the following general formula (I) dispersed by dissolution 
in a high boiling organic solvent in a weight ratio of the high boiling 
organic solvent to the yellow color forming coupler of 0.6 or more: 
##STR2## 
wherein X represents an organic residue necessary for forming a 
nitrogen-containing heterocycle with a nitrogen atom; Y represents an 
aromatic group or a heterocyclic group; Z represents a group which is 
eliminatable by reaction of the coupler represented by general formula (I) 
with an oxidation product of a developing agent; and 
##STR3## 
is hereinafter referred to as A. 
In a preferred embodiment, the high boiling organic solvent has a 
dielectric constant of 6.0 or less. 
In an even more preferred embodiment, the high boiling organic solvent is 
represented by one of the following general formulae (S-1) to (S-5): 
##STR4## 
In formula (S-1), R.sub.1, R.sub.2 and R.sub.3 each independently 
represents an alkyl group, a cycloalkyl group, an aryl group, an alkoxy 
group, a cycloalkyloxy group or an aryloxy group. In formula (S-2), 
R.sub.4 and R.sub.5 each independently represents an alkyl group, a 
cycloalkyl group or an aryl group, R.sub.6 represents a halogen atom such 
as F, Cl, Br or I, an alkyl group, an alkoxy group, an aryloxy group or an 
alkoxycarbonyl group, and a represents an integer of 0 to 3, with the 
proviso that when a is 2 or more, a plurality of R.sub.6 s may be the same 
or different. In formula (S-3), Ar represents an aryl group, b represents 
an integer of 1 to 6, and R.sub.7 represents a b-valent hydrocarbon group 
or a hydrocarbon group bonded through an ether linkage to each other. In 
formula (S-4), R.sub.8 represents an alkyl group or a cycloalkyl group, c 
represents an integer of 1 to 6, and R.sub.9 represents a c-valent 
hydrocarbon group or a hydrocarbon group bonded through an ether linkage. 
In formula (S-5), d represents an integer of 2 to 6, R.sub.10 represents 
d-valent hydrocarbon group (excluding an aromatic group), and R.sub.11 
represents an alkyl group, a cycloalkyl group or an aryl group. 
In another embodiment, the yellow color forming silver halide emulsion 
layer contains a water-insoluble polymer. 
In even another embodiment, the weight ratio of the water-insoluble polymer 
to the yellow coupler in the yellow color forming silver halide emulsion 
layer is 0.2 or more. 
In a further embodiment, at least one cyan color forming silver halide 
emulsion layer, at least one magenta color forming silver halide emulsion 
layer and at least one of said yellow color forming silver halide emulsion 
layer, which are different from one another in color sensitivity, are 
formed on the support.

DETAILED DESCRIPTION OF THE INVENTION 
In the couplers represented by general formula (I) the nitrogen-containing 
heterocycle represented by A has one or more carbon atoms, preferably 1 to 
20 carbon atoms, and more preferably 2 to 12 atoms, and may be saturated 
or unsaturated, a single ring or a condensed ring, and substituted or 
unsubstituted. The ring may contain an oxygen atom, a sulfur atom or a 
phosphorus atom in addition to the nitrogen atom. More than one atom may 
be contained in each of these heteroatoms. The number of the ring members 
is 3 or more, preferably 3 to 12, and more preferably 5 or 6. 
Specific examples of the heterocycles represented by A include pyrrolidino, 
piperidino, morpholino, 1-imidazolidinyl, 1-pyrazolyl, 1-piperazinyl, 
1-indolinyl, 1,2,3,4-tetrahydroquinoxaline-1-yl, 1-pyrrolinyl, 
pyrazolidine-1-yl, 2,3-dihydro-1-indazolyl, isoindoline-2-yl, 1-indolyl, 
1-pyrrolyl, benzothiazine-4-yl, 4-thiazinyl, benzodiazine-1-yl, 
aziridine-1-yl, benzooxazine-4-yl, 2,3,4,5-tetrahydroquinolyl and 
phenoxazine-10-yl. 
In general formula (I), the aromatic group represented by Y has 6 or more 
carbon atoms, and preferably 6 to 10 carbon atoms, and may be substituted 
or unsubstituted. Particularly preferred examples of such aromatic groups 
include phenyl and naphthyl. 
In general formula (I), the heterocyclic group represented by Y has one or 
more carbon atoms, preferably 1 to 10 carbon atoms, and more preferably 2 
to 5 carbon atoms, and may be saturated or unsaturated, and substituted or 
unsubstituted. Preferred examples of the heteroatoms include a nitrogen 
atom, a sulfur atom and an oxygen atom. The number of the ring members is 
preferably 5 or 6, but others may be used. The ring may be either a single 
ring or a condensed ring. Specific examples of the heterocyclic groups 
represented by Y include 2-pyridyl, 4-pyrimidinyl, 5-pyrazolyl, 
8-quinolyl, 2-furyl and 2-pyrrolyl. 
When the groups represented by A and Y in general formula (I) each have 
substituents, examples of the substituents include halogen atoms such as 
fluorine and chlorine, alkoxycarbonyl groups having 2 to 30, preferably 2 
to 20 carbon atoms, such as methoxycarbonyl, dodecyloxycarbonyl and 
hexadecyloxycarbonyl groups, acylamino groups having 2 to 30, preferably 2 
to 20 carbon atoms, such as acetamido, tetra-decaneamido, 
2-(2,4-di-t-amylphenoxy)butaneamido and benzamido groups, sulfonamido 
groups having 1 to 30, preferably 1 to 20 carbon atoms, such as 
methanesulfonamido, dodecanesulfonamido, hexadecanesulfonamido and 
benzenesulfonamido groups, carbamoyl groups having 2 to 30, preferably 2 
to 20 carbon atoms, such as N-butylcarbamoyl and N,N-diethylcarbamoyl 
groups, sulfamoyl groups having 1 to 30, preferably 1 to 20 carbon atoms, 
such as N-butylsulfamoyl, N-dodecylsulfamoyl, N-hexadecylsulfamoyl and 
N-3-(2,4-di-t-amylphenoxy)butylsulfamoyl groups, alkoxy groups having 1 to 
30, preferably 1 to 20 carbon atoms, such as methoxy and dodecyloxy 
groups, N-acylsulfamoyl groups having 2 to 30, preferably 2 to 20 carbon 
atoms, such as N-propanoylsulfamoyl and N-tetradecanoylsulfamoyl groups, 
sulfonyl groups having 1 to 30, preferably 1 to 20 carbon atoms, such as 
methanesulfonyl, octanesulfonyl and dodecanesulfonyl groups, 
alkoxycarbonylamino groups having 1 to 30, preferably 1 to 20 carbon 
atoms, such as methoxycarbonylamino and tetradecyloxycarbonylamino groups, 
a cyano group, a nitro group, a carboxyl group, aryloxy groups having 6 to 
20, preferably 6 to 10 carbon atoms, such as phenoxy and 4-chlorophenoxy 
groups, alkylthio groups having 1 to 30, preferably 1 to 20 carbon atoms, 
such as methylthio and dodecylthio groups, ureido groups having 1 to 30, 
preferably 1 to 20 carbon atoms, such as a phenylureido group, aryl groups 
having the same meaning as described when Y represents an aromatic group, 
heterocyclic groups having the same meaning as described when Y represents 
a heterocyclic group, a sulfo group, alkyl groups having 1 to 30, 
preferably 1 to 20 carbon atoms, which are straight, branched, cyclic, 
saturated, unsaturated, substituted or unsubstituted, such as methyl, 
ethyl, isopropyl, cyclopropyl, trifluoromethyl, cyclopentyl, dodecyl and 
2-hexyloctyl groups, acyl groups having 1 to 30, preferably 2 to 20 carbon 
atoms, such as acetyl and benzoyl groups, arylthio groups having 6 to 20, 
preferably 6 to 10 carbon atoms, such as a phenylthio group, 
sulfamoylamino groups having 0 to 30, preferably 0 to 20 carbon atoms, 
such as N-butylsulfamoylamino and N-dodecylsulfamoylamino groups, 
N-acylcarbamoyl groups having 2 to 30, preferably 2 to 20 carbon atoms, 
such as a N-dodecanoylcarbamoyl group, N-sulfonylcarbamoyl groups having 1 
to 30, preferably 2 to 20, carbon atoms, such as 
N-hexadecanesulfonylcarbamoyl, N-benzenesulfonylcarbamoyl and 
N-(2-octyloxy-5-tert-octylbenzenesulfonyl)carbamoyl groups, 
N-sulfamoylcarbamoyl groups having 1 to 30, preferably 1 to 20 carbon 
atoms, such as N-(ethylsulfamoyl)carbamoyl and 
N-{3-(2,4-di-t-amylphenoxy)propylsulfamoyl}carbamoyl groups, 
N-sulfonylsulfamoyl groups having 0 to 30, preferably 1 to 20 carbon 
atoms, such as N-dodecanesulfonylsulfamoyl and N-benzenesulfonylsulfamoyl 
groups, N-carbamoylsulfamoyl groups having 1 to 30, preferably 1 to 20 
carbon atoms, such as N-(ethylcarbamoyl)sulfamoyl and 
N-{3-(2,4-di-t-amylphenoxy)propylcarbamoyl}sulfamoyl groups, 
N-(N-sulfonylcarbamoyl)sulfamoyl groups having 1 to 30, preferably 1 to 20 
carbon atoms, such as N-(dodecanesulfonylcarbamoyl)sulfamoyl and 
N-(2-octyloxy-5-t-octylbenzenesulfonylcarbamoyl)sulfamoyl groups, 
3-sulfonylureido groups having 1 to 30, preferably 1 to 20 carbon atoms, 
such as 3-hexadecanesulfonylureido and 3-benzenesulfonylureido groups, 
3-acylureido groups having 2 to 30, preferably 2 to 20 carbon atoms, such 
as 3-acetylureido and 3-benzoylureido groups, 3-acylsulfamido groups 
having 1 to 30, preferably 1 to 20 carbon atoms, such as 
3-propionylsulfamido and 3-(2,4-dichlorobenzoyl)sulfamido groups, 
3-sulfonylsulfamido groups having 0 to 30, preferably 1 to 20 carbon 
atoms, such as 3-methanesulfonylsulfamido and 
3-(2-methoxyethoxy-5-t-octylbenzenesulfonyl)sulfamido groups, a hydroxyl 
group, acyloxy groups having 1 to 30, preferably 1 to 20 carbon atoms, 
such as propanoyloxy and tetradecanoyloxy groups, sulfonyloxy groups 
having 0 to 30, preferably 0 to 20 carbon atoms, such as 
dodecanesulfonyloxy and 2-octyloxy-5-t-octylbenzene-sulfonyloxy groups and 
aryloxycarbonyl groups having 7 to 20, preferably 7 to 10 carbon atoms, 
such as a phenoxycarbonyl group. 
When the groups represented by A have substituents, preferred examples of 
the substituents include the halogen atoms, alkoxy groups, acylamino 
groups, carbamoyl groups, alkyl groups, sulfonamido groups and nitro 
groups, of the groups enumerated above. However, unsubstituted groups are 
also preferred examples. 
When the groups represented by Y have substituents, preferred examples of 
the substituents include the halogen atoms, alkoxycarbonyl groups, 
sulfamoyl groups, carbamoyl groups, sulfonyl groups, sulfonamido groups, 
acylamino groups, alkoxy groups, aryloxy groups, N-acylcarbamoyl groups, 
N-sulfonylcarbamoyl groups, N-sulfamoylcarbamoyl groups, 
N-sulfonylsulfamoyl groups, N-acylsulfamoyl groups, N-carbamoylsulfamoyl 
groups and N-(N-sulfonylcarbamoyl)sulfamoyl groups. 
The group represented by Z in general formula (I) may be any of coupling 
eliminatable groups previously known. Preferred examples thereof include 
nitrogen-containing heterocyclic groups which are bonded to coupling 
positions at the nitrogen atoms, aromatic oxy groups, aromatic thio 
groups, heterocyclically oxy groups, heterocyclic thio groups, acyloxy 
groups, carbamoyloxy groups, alkylthio groups and halogen groups. These 
eliminatable groups may be any of photographic useful groups or precursors 
thereof such as development inhibitors, development accelerators, 
desilverization accelerators, fogging agents, dyes, hardening agents, 
couplers, developing agent oxidation product scavengers, fluorescent dyes, 
developing agents and electron transfer agents, and non-photographically 
useful groups. 
The nitrogen-containing heterocyclic group represented by Z is preferably a 
substituted or unsubstituted heterocyclic group of a single or condensed 
ring. Examples thereof include succinimido, maleinimido, phthalimido, 
diglycolimido, pyrrolino, pyrazolyl, imidazolyl, 1,2,4-triazole-1-yl (or 
4-yl) , 1-tetrazolyl, indolyl, benzopyrazolyl, benzimidazolyl, 
benzotriazolyl, imidazolidine-2,4-dione-3-yl (or 1-yl), 
oxazolidine-2,4-dione-3-yl, thiazolidine-2,4-dione-3-yl, 
imidazoline-2-one-1-yl, oxazoline-2-one-3-yl, thiazoline-2-one-3-yl, 
benzooxazoline-2-one-3-yl, 1,2,4-triazolidine-3,5-dione-4-yl, 
2-pyridone-1-yl, morpholine-3,5-dione-4-yl, 1,2,3-triazole-1-yl and 
2-imidazoline-5-one group. 
When the heterocyclic groups have substituents, examples of the 
substituents include the substituents enumerated for the above-described 
groups represented by A. 
Preferred examples of the nitrogen-containing heterocyclic groups 
represented by include 1-pyrazolyl, imidazolyl, 1,2,3-triazole-l-yl, 
benzotriazolyl, 1,2,4-triazole-l-yl, oxazolidine-2,4-dione-3-yl, 
1,2,4-triazolidine- 3,5-dione-4-yl and imidazolidine-2,4-dione-3-yl. These 
groups may also be substituted. 
The aromatic oxy group represented by Z is preferably a substituted or 
unsubstituted phenoxy group. When the phenoxy group has a substituent, 
examples of the substituents include the substituents enumerated for the 
above-described groups represented by Y. Preferred examples thereof 
include those groups having at least one electron attractive substituent, 
such as the sulfonyl, alkoxycarbonyl, sulfamoyl, halogen, carboxyl, 
carbamoyl and nitro groups. 
The aromatic thio group represented by Z is preferably a substituted or 
unsubstituted phenylthio group. When the phenylthio group has a 
substituent, examples of the substituents include the substituents 
enumerated for the above-described groups represented by Y. In the case of 
the phenylthio group, it is preferred that at least one substituent is 
alkyl, alkoxy, sulfonyl, alkoxycarbonyl, sulfamoyl, halogen, carbamoyl or 
nitro. 
When Z represents the heterocyclic oxy group, the heterocyclic moiety has 
the same meaning as described above when Y represents a heterocyclic 
group. 
The heterocyclic thio group represented by Z is preferably a 5- or 
6-membered unsaturated heterocyclic thio group. Examples thereof include 
tetrazolylthio, 1,3,4-thiazolylthio, 1,3,4-oxadiazolylthio, 
1,3,4-triazolylthio, benzoimidazolylthio, benzothiazolylthio and 
2-pyridylthio groups. When these groups have substituents, examples of the 
substituents include the substituents enumerated for the above-described 
heterocyclic groups represented by Y. Of those, particularly preferred 
substituents include aromatic groups, alkyl groups, alkylthio groups, 
acylamino groups, alkoxycarbonyl groups and aryloxycarbonyl groups. 
Examples of the acyloxy group represented by Z include an aromatic acyloxy 
group having 7 to 11 carbon atoms, and preferably is benzoyloxy group, or 
an aliphatic acyloxy group having 2 to 20, preferably 2 to 10 carbon 
atoms, which may have a substituent. Specific examples of the substituents 
include the substituents enumerated for the above-described aromatic 
groups represented by Y. It is preferred that at least one substituent is 
a halogen atom, a nitro group, an aryl group, an alkyl group or an alkoxy 
group. 
The carbamoyloxy group represented by Z is preferably an aliphatic, 
aromatic, heterocyclic or unsubstituted carbamoyloxy group having 1 to 30 
carbon atoms, preferably 1 to 20 carbon atoms. Examples thereof include 
N,N-diethylcarbamoyloxy, N-phenylcarbamoylmorpholinocarbonyloxy, 
1-imidazolylcarbonyloxy and N,N-dimethylcarbamoyloxy, wherein detailed 
descriptions of alkyl, aromatic and heterocyclic groups have the same 
meanings as defined in the above descriptions for Y. 
The alkylthio group represented by Z preferably has 1 to 30 carbon atoms, 
preferably 1 to 20 carbon atoms. Details of the alkylthio group are the 
same as defined in the above description for Y. 
Preferred examples of the groups represented by Z in general formula (I) 
include 5- or 6-membered nitrogen-containing heterocyclic groups which are 
bonded to coupling positions at the nitrogen atoms, aromatic oxy groups, 
5- or 6-membered heterocyclic oxy groups and 5- or 6-membered heterocyclic 
thio groups. 
The groups represented by Y in general formula (I) are preferably aromatic 
groups. A phenyl group having at least one substituent at the ortho 
position is particularly preferred. Examples of the substituents include 
the substituents mentioned for the above-described aromatic groups 
represented by Y. 
When the group represented by Y in general formula (I) is the phenyl group 
having at least one substituent at the ortho position, a halogen atom, an 
alkoxy group, an alkyl group or an aryloxy group is particularly preferred 
as the substituent at the ortho position. 
Of the couplers represented by general formula (I), particularly preferred 
couplers are represented by the following general formula (II): 
##STR5## 
wherein Y and Z have the same meanings as described in general formula 
(I); X.sub.1 represents an organic residue necessary for forming a 
nitrogen-containing heterocycle with --C(R.sub.1 R.sub.2)--N--; R.sub.1 
and R.sub.2 each represents a hydrogen atom or a substituent; and 
##STR6## 
is hereinafter referred to as B. 
Preferred examples and specific examples of Y and Z are the same as 
described above for general formula (I). 
Specific examples of the heterocyclic groups represented by B in general 
formula (II), and examples of the substituents thereof, include the 
heterocyclic groups and substituents described for A in general formula 
(I). Preferred examples thereof are also the same as described for A in 
general formula (I). It is particularly preferred that these 
nitrogen-containing heterocyclic groups are benzene condensed rings. 
Of the couplers represented by general formula (II), more preferred 
couplers are represented by the following general formula (III): 
##STR7## 
wherein R.sub.3 represents a hydrogen atom or a substituent; R.sub.4, 
R.sub.5 and R.sub.6 represent substituents; Z has the same meaning as 
described for general formula (I); m and n each represent an integer of 0 
to 4; with the proviso that when m and n each represent an integer of 2 or 
more, R.sub.4 and R.sub.6, which may be the same or different, may combine 
to form a ring. 
Examples of the substituents represented by R.sub.3 and R.sub.4 in general 
formula (III) are the same as the examples of the substituents of the 
groups represented by A in general formula (I). Preferred examples of the 
groups represented by R.sub.3 include hydrogen, alkoxy and aryl, and 
preferred examples of the groups represented by R.sub.4 include halogen, 
alkoxy, acylamino, carbamoyl, alkyl, sulfonamido and nitro. m is 
preferably an integer of 0 to 2, more preferably, 0 or 1. 
Examples of the substituents represented by R.sub.5 and R.sub.6 in general 
formula (III) include the same examples as described for the substituents 
of the groups represented by Y in general formula (I). R.sub.5 is 
preferably halogen, alkoxy, alkyl or aryloxy. Preferred examples of the 
groups represented by R.sub.6 include the same examples as described for 
the preferred substituents of the groups represented by Y in general 
formula (I). n is preferably an integer of 0 to 2, more preferably, 1 or 
2. 
The couplers represented by general formulae (I), (II) and (III) may 
combine at X, Y and Z through divalent or higher valent groups to form 
dimers or polymers. In this case, the number of the carbon atoms may be 
excluded from the range defined above for each of the substituents. 
Specific examples of the couplers represented by general formula (I) 
include, but are not limited to, the following compounds. 
3 
##STR8## 
No. R.sub.3 m R.sub.4 R.sub.5 n R.sub.6 Z 
1 H 0 -- OCH.sub.3 1 
##STR9## 
##STR10## 
2 " " -- OC.sub.18 H.sub.37 
(n) 1 
##STR11## 
" 3 " " -- OC.sub.12 H.sub.25 
(n) 1 5-SO.sub.2 NHCONHC.sub.3 
H.sub.7 " 
4 " " -- 
##STR12## 
1 
##STR13## 
" 
5 H 0 -- 
##STR14## 
1 
5-SO.sub.2 NHCOC.sub.2 
H.sub.5 
##STR15## 
6 " " -- 
##STR16## 
1 
5-SO.sub.2 NHCOC.sub.2 H.sub.5 " 
7 " " -- 
##STR17## 
1 
5-SO.sub.2 NHCOCH.sub.3 " 
8 " " -- 
##STR18## 
1 
##STR19## 
" 
9 " " -- 
##STR20## 
1 
##STR21## 
" 
10 H 0 -- 
##STR22## 
1 
5-CONHSO.sub.2 C.sub.12 
H.sub.25 
##STR23## 
11 " " -- 
##STR24## 
1 
4-SO.sub.2 NHCOC.sub.9 H.sub.19 " 
12 " " -- " 2 4-Cl-5-CONHSO.sub.2 C.sub.16 
H.sub.33 (n) " 
13 " " -- " 2 3-Cl-5-CONHCOC. 
sub.11 H.sub.23 " 
14 " " -- OCH.sub.3 2 3-Cl-5-CONHSO.sub. 
2 C.sub.12 H.sub.25 (n) " 15 H 0 -- OC.sub.16 H.sub.33 
(n) 1 
##STR25## 
##STR26## 
16 " " -- 
##STR27## 
1 
##STR28## 
" 
17 " " -- OCH(CH.sub.3).sub.2 1 
##STR29## 
" 18 " " -- OC.sub.18 H.sub.37 
(n) 1 
##STR30## 
" 
19 H 0 -- 
##STR31## 
1 
##STR32## 
##STR33## 
20 " " -- OC.sub.2 
H.sub.5 1 " 
##STR34## 
21 " " -- OC.sub.18 H.sub.37 
(n) 2 4-Cl-5-CONHSO.sub.2 C.sub.12 
H.sub.25 
##STR35## 
22 " " -- " 1 
##STR36## 
" 
23 H 0 -- 
##STR37## 
1 
##STR38## 
##STR39## 
24 " " -- OCH(CH.sub.3).sub.2 1 
##STR40## 
" 25 CH.sub.3 " -- OC.sub.2 
H.sub.5 1 
##STR41## 
" 26 H " -- OC.sub.18 H.sub.37 
(n) 1 
##STR42## 
##STR43## 
27 H 0 -- 
##STR44## 
1 
##STR45## 
##STR46## 
28 " 0 -- OC.sub.16 H.sub.33 
(n) 1 5-SO.sub.2 NHCOC.sub.2 H.sub. 
5 
##STR47## 
29 " 0 -- Cl 1 5 
-CONHSO.sub.2C.sub.16 H.sub.33 
(n) 
##STR48## 
30 " 0 -- " 1 
##STR49## 
##STR50## 
31 H 0 -- Cl 1 
##STR51## 
##STR52## 
32 " 0 -- " 2 4 
-Cl-5-COOC.sub.12 
H.sub.25 
##STR53## 
33 " 0 -- " 2 
##STR54## 
##STR55## 
34 " 0 -- " 1 5 
-SO.sub.2 NHC.sub.12 H.sub.25 " 
35 " 0 -- " 1 5-SO.sub.2 NHSO.sub.2 C.sub.16 
H.sub.33 
(n) 
##STR56## 
36 H 1 5-NO.sub.2 Cl 1 
##STR57## 
##STR58## 
37 " 2 5,7-Br " 1 5 
-NHSO.sub.2 C.sub.16 H.sub.33 (n) " 38 " 0 -- C.sub.18 H.sub.37 (n) 1 
##STR59## 
##STR60## 
39 " 0 -- " 1 " 
##STR61## 
40 " 0 -- 
##STR62## 
1 
##STR63## 
" 
41 H 1 5-Cl Cl 1 5-N 
HSO.sub.2 C.sub.16 
H.sub.33 
##STR64## 
42 
##STR65## 
1 5-NO.sub.2 OC.sub.14 
H.sub.29 1 
##STR66## 
##STR67## 
43 H 1 5-Br Cl 1 
##STR68## 
##STR69## 
44 H 1 " " 1 " 
##STR70## 
45 " 1 5-Cl " 1 5 
-NHSO.sub.2 C.sub.12 
H.sub.25 
##STR71## 
46 H 1 5-NO.sub.2 Cl 1 5 
-NHSO.sub.2 C.sub.12 
H.sub.25 
##STR72## 
47 " 0 -- " 1 
##STR73## 
##STR74## 
48 " 1 5-OCH.sub.3 " 2 4 
-Cl-5-COOC.sub.12 
H.sub.25 
##STR75## 
49 " 1 5-NO.sub.2 CF.sub.3 1 
##STR76## 
##STR77## 
50 H 0 -- OC.sub.2 
H.sub.5 1 5-SO.sub.2 C.sub.12 
H.sub.25 
##STR78## 
51 " 0 -- Cl 1 
##STR79## 
" 52 C.sub.2 
H.sub.5 0 -- " 1 
##STR80## 
##STR81## 
53 H 0 -- " 1 
##STR82## 
##STR83## 
54 H 0 -- Cl 1 5 
-SO.sub.2 NHCOC.sub.11 
H.sub.23 
##STR84## 
55 H 0 -- 
##STR85## 
1 
##STR86## 
##STR87## 
56 H 1 Br 
##STR88## 
1 
##STR89## 
" 
57 H 0 -- 
##STR90## 
1 
##STR91## 
" 
58 H 0 -- 
##STR92## 
1 5-SO.sub.2 NHC.sub.14 
H.sub.29 
##STR93## 
59 " " -- 
##STR94## 
1 5-SO.sub.2 NHCONHC.sub.12 
H.sub.25 
##STR95## 
60 " " -- 
##STR96## 
1 5-NHSO.sub.2 C.sub.16 H.sub.33 
(n) 
##STR97## 
61 " " -- 
##STR98## 
1 
##STR99## 
##STR100## 
62 H 0 -- 
##STR101## 
1 
##STR102## 
##STR103## 
63 " 1 5-NO.sub.2 " 1 " 
##STR104## 
64 " 1 5-NHSO.sub.2 
CH.sub.3 
##STR105## 
1 5-SO.sub.2 
NH.sub.2 
##STR106## 
65 " 0 -- 
##STR107## 
2 
##STR108## 
" 
66 CH.sub.3 1 5-Br 
##STR109## 
1 
##STR110## 
##STR111## 
67 H 0 -- 
##STR112## 
1 
##STR113## 
##STR114## 
68 " 1 5-Br OC.sub.12 
H.sub.25 1 
##STR115## 
" 
69 " 0 -- 
##STR116## 
1 
##STR117## 
" 
70 " 0 -- 
##STR118## 
1 
##STR119## 
##STR120## 
##STR121## 
No. 
##STR122## 
Y Z 
71 
##STR123## 
##STR124## 
##STR125## 
72 
##STR126## 
##STR127## 
" 
73 
##STR128## 
##STR129## 
##STR130## 
74 
##STR131## 
##STR132## 
##STR133## 
75 
##STR134## 
##STR135## 
##STR136## 
76 
##STR137## 
##STR138## 
##STR139## 
77 
##STR140## 
##STR141## 
##STR142## 
78 
##STR143## 
##STR144## 
SCH.sub.2 COOH 
79 
##STR145## 
##STR146## 
##STR147## 
80 " " 
##STR148## 
(81) 
##STR149## 
(82) 
##STR150## 
The compounds of the present invention can be synthesized by methods 
generally known in the art or similar methods. 
For example, the compounds can be synthesized by the following synthesis 
route: 
##STR151## 
In the above synthesis, X, Y and Z have the same meanings as described 
above for general formula (I); R.sub.10 represents a halogen atom such as 
chlorine, --OH, an alkoxy group such as methoxy or ethoxy or a phenoxy 
group such as phenoxy or 4-nitrophenoxy; and Hal represents a halogen. 
Under reaction conditions of (a), when R.sub.10 is --OH, a dehydrating 
condensing agent such as N,N-dicyclohexylcarbodiimide or 
N,N-diisopropylcarbodiimide is used. When R.sub.10 is a halogen atom, the 
reaction is conducted in the presence of a dehydrohalogenating agent. The 
dehydrohalogenating agents used include organic bases such as 
triethylamine, diisopropylethylamine, pyridine, guanidine and 
butoxypotassium, and inorganic bases such as sodium hydroxide, potassium 
hydroxide, sodium hydride and potassium carbonate. In the reaction of 
compound 3 to compound 4, a halogenating agent is used as (b). Examples of 
halogenating agents include bromine, chlorine, N-bromosuccinimide and 
N-chlorosuccinimide. In the reaction of compound 4 to the end product, a 
dehydrohalogenating agent is generally used as (c). Examples thereof 
include the organic and inorganic bases described above. In each reaction, 
a reaction solvent is used. Examples of the solvents include chlorine type 
solvents such as dichloromethylene, aromatic type solvents such as 
benzene, chlorobenzene and toluene, amide type solvents such as 
N,N-dimethylformamide, N,N-dimethylacetamide and N-methylpyrrolidone, 
nitrile type solvents such as acetonitrile and propionitrile, ether type 
solvents such as tetrahydrofuran and ethylene glycol diethyl ether, 
sulfone type solvents such as dimethyl sulfone and sulfolane and 
hydrocarbon type solvents such as cyclohexane and n-hexane. 
The compounds of the present invention can also be synthesized by methods 
other than the above-described synthesis route. One example is the method 
described in J. Org. Chem., 29, 2932 (1964). In some cases, product 5 is 
converted to a desired end product by further conversion of a functional 
group. The modification of the synthesis route and additional reaction can 
be appropriately selected. 
Specific syntheses are described below. Other example compounds can be 
synthesized in a similar manner. 
SYNTHESIS EXAMPLE 1 
Synthesis of Example Compound (54) 
Synthesis was conducted by the following method: 
##STR152## 
3.5 g of compound (6) and 14 g of compound (7) were dissolved in 100 ml of 
N,N-dimethylformamide and 100 ml of acetonitrile. To the resulting 
solution, 40 ml of an acetonitrile solution in which 6 g of 
N,N'-dicyclohexylcarbodiimide was dissolved, was added dropwise at room 
temperature. After reaction for 2 hours, precipitated N,N-dicyclohexylurea 
was separated by filtration. The filtrate was poured on 500 ml of water, 
and extracted with 500 ml of ethyl acetate. The oil layer was collected 
using a separatory funnel, and washed with water, followed by drying with 
Glauber's salt. The solvent was distilled off under reduced pressure, and 
hexane was added to the residue, followed by crystallization. As a result, 
17.2 g of compound (8) was obtained. 
16 g of compound (8) was mixed with 150 ml of dichloromethane. 10 ml of 
dichloromethane solution containing 4.8 g of bromine was added dropwise 
under ice cooling (5.degree. to 10.degree. C.). After reaction for 10 
minutes, the reaction product was transferred into a separatory funnel, 
and washed with water. The oil layer, a solution containing compound (9), 
was collected to use in a subsequent step. 
8.1 g of 5,5-dimethyl-2,4-dioxo-1,3-oxazolidine and 8.8 ml of triethylamine 
were added to 160 ml of N,N-dimethylformamide. The dichloromethane 
solution of compound (9) obtained above was added dropwise to this 
solution at room temperature. After reaction for 1 hour, 500 ml of ethyl 
acetate was added. The resulting solution was transferred into a 
separatory funnel, and washed with water. After neutralization with 
diluted hydrochloric acid, the solution was washed with water again, and 
the oil layer was separated. The solvent was distilled off under reduced 
pressure, and the residue was separated and purified by column 
chromatography. Silica gel was used as a packing, and ethyl acetate/hexane 
(1/1) was used as an elute. Fractions containing desired example compound 
(54) were collected, and the solvent was distilled off under reduced 
pressure to obtain 15.2 g of waxy example compound (54). 
SYNTHESIS EXAMPLE 2 
Synthesis of Example Compound (2) 
Synthesis was conducted in a manner similar to that of Synthesis Example 1 
described above, with the exception that compound (7) was substituted with 
an equimolar amount of the following compound (10): 
##STR153## 
The end product was purified by column chromatography to obtain 18.3 g of 
waxy example compound (2). 
The couplers of the present invention are used preferably in an amount of 
0.01 to 10 mmol/m.sup.2, more preferably in an amount of 0.05 to 5 
mmol/m.sup.2, and most preferably in an amount of 0.1 to 3 mmol/m.sup.2. 
Silver halides are used with respect to the couplers of the present 
invention in a molar ratio of 0.1 to 100, preferably in a molar ratio of 
0.5 to 20, more preferably in a molar ratio of 1.5 to 10, and most 
preferably in a molar ratio of 2.0 to 6.0. 
In the present invention, various conventional dispersing methods can be 
used to introduce lipophilic photographic organic compounds such as 
couplers into photographic materials. 
According to the oil-in-water dispersion method described in U.S. Pat. No. 
2,322,027, the lipophilic photographic organic compounds can be dissolved 
in high boiling organic solvents having a boiling point of about 
175.degree. C. or more at atmospheric pressure such as phthalates, 
phosphates, benzoates, fatty acid esters, amides, phenols, alcohols, 
carboxylic acids, N,N-dialkylanilines, hydrocarbons, oligomers and 
polymers, and/or low boiling organic solvents having a boiling point of 
about 30.degree. to about 160.degree. C. at atmospheric pressure such as 
esters (e.g., ethyl acetate, butyl acetate, ethyl propionate, 
.beta.-ethoxyethyl acetate and methyl cellosolve acetate), alcohols (e.g., 
sec-butyl alcohol), ketones (e.g., methyl isobutyl ketone, methyl ethyl 
ketone and cyclohexanone), amides (e.g., dimethylformamide and 
N-methylpyrrolidone) and ethers (e.g., tetrahydrofuran and dioxane), 
followed by dispersion by emulsification in hydrophilic colloids such as 
gelatin. 
The high boiling organic solvents used in the present invention may be in 
any of liquid, waxy and solid forms. As the high boiling organic solvents 
used for the above-described yellow couplers of the present invention, the 
high boiling organic solvents having a dielectric constant (25.degree. C., 
1 atm., 10 KHz) of 6.0 or less, preferably 3.5 to 5.5, are preferred among 
others in terms of the best hue of color forming dyes and fastness to 
light. 
Further, with respect to color forming properties and other photographic 
characteristics, the high boiling solvents represented by any of the 
above-described general formulae (S-1) to (S-5) are preferably used. For 
the object of the present invention, the high boiling organic solvents 
having a dielectric constant of 6.0 or less and represented by any of the 
above-described general formulae (S-1) to (S-5) are more preferred. 
General formulae (S-1) to (S-5) are hereinafter described. 
##STR154## 
In general formula (S-1), R.sub.1, R.sub.2 and R.sub.3 each independently 
represents an alkyl group, a cycloalkyl group, an aryl group, an alkoxy 
group, a cycloalkyloxy group or an aryloxy group. 
##STR155## 
In general formula (S-2), R.sub.4 and R.sub.5 each independently represents 
an alkyl group, a cycloalkyl group or an aryl group, R.sub.6 represents a 
halogen atom such as F, Cl, Br or I, an alkyl group, an alkoxy group, an 
aryloxy group or an alkoxycarbonyl group, and a represents an integer of 0 
to 3, with the proviso that when a is 2 or more, a plurality of R.sub.6 s 
may be the same or different. 
##STR156## 
In general formula (S-3), Ar represents an aryl group, b represents an 
integer of 1 to 6, and R.sub.7 represents a b-valent hydrocarbon group or 
a hydrocarbon group bonded through an ether linkage to each other. 
##STR157## 
In general formula (S-4), R.sub.8 represents an alkyl group or a cycloalkyl 
group, c represents an integer of 1 to 6, and R.sub.9 represents a 
c-valent hydrocarbon group or a hydrocarbon group bonded through an ether 
linkage to each other. 
##STR158## 
In general formula (S-5), d represents an integer of 2 to 6, R.sub.10 
represents d-valent hydrocarbon group (excluding an aromatic group), and 
R.sub.11 represents an alkyl group, a cycloalkyl group or an aryl group. 
Specific examples of the high boiling organic solvents used in the present 
invention are enumerated below: 
Compounds represented by formula (S-1); 
##STR159## 
Compounds represented by formula (S-2); 
##STR160## 
Compounds represented by formula (S-3); 
##STR161## 
Compounds represented by formula (S-4); 
##STR162## 
Compounds represented by formula (S-5); 
##STR163## 
Other high boiling organic solvents which can be used according to the 
present invention in addition to those described above, and/or methods for 
producing them are described, for example, in U.S. Pat. Nos. 2,322,027, 
2,533,514, 2,772,163, 2,835,579, 3,676,137, 3,912,515, 3,936,303, 
4,080,209, 4,127,413, 4,193,802, 4,239,851, 4,278,757, 4,363,873, 
4,483,918 and 4,745,049, European Patent 276,319A, JP-A-48-47335, 
JP-A-51-149028, JP-A-61-84641, JP-A-62-118345, JP-A-62-247364, 
JP-A-63-167357, JP-A-64-68745 and JP-A-l-101543. 
The weight ratio of the high boiling organic solvents, to the yellow 
couplers of the present invention is 0.6 or more, preferably 0.6 to 5.0, 
more preferably 0.8 to 4.0, and most preferably 1.0 to 3.0. 
A weight ratio of less than 0.6 causes a remarkable deterioration in light 
fastness, and a weight ratio exceeding 5.0 is liable to produce the 
problems of deterioration in film property and generation of stains formed 
by a lapse of time after processing. If gelatin is applied in an increased 
amount to avoid deterioration of the film property, the problem of 
prolonged drying time arises. 
In order to further improve the light fastness of yellow images formed from 
the yellow couplers of the present invention as well as other yellow 
couplers, it is preferred that water-insoluble polymers are added to the 
silver halide emulsion layers containing the yellow couplers. 
The water-insoluble polymers which can be used in the present invention 
include the polymers described in PCT International Publication No. 
WO88/00723 and JP-A-63-44658. 
However, any polymers may be used in the present invention, so long as they 
are water-insoluble. Vinyl polymers in which repeating units have 
--(C.dbd.O)-- linkages and polyester type polymers are preferably used. 
As to vinyl monomers preferably used for synthesis of the polymers used in 
the present invention, two or more types of monomers are used as 
comonomers, corresponding to various purposes (for example, an improvement 
in solubility). For control of color forming property or solubility, an 
acid group-containing monomer may be used as the comonomer, so long as the 
copolymer does not become water-soluble. Further, a monomer having two or 
more cross-linkable ethylenic unsaturated components can be used. As such 
monomers, those described in JP-A-60-151636 are preferably used. 
When the hydrophilic monomer (which means here a monomer providing a 
water-soluble homopolymer) is used as the comonomer in the vinyl monomer, 
there is no particular limitation on the ratio of the hydrophilic monomer 
to the synthesized copolymer, so long as the copolymer does not become 
water-soluble. However, usually the ratio will preferably be 40 mol % or 
less, more preferably 20 mol % or less, and most preferably 10 mol % or 
less. Furthermore, when the hydrophilic comonomer which is copolymerized 
with the monomer, has an acid group, the ratio of the comonomer having the 
acid group to the copolymer is usually 20 mol % or less, and preferably 10 
mol % or less, from the viewpoint of image keeping quality. However, it is 
most preferred that such a comonomer is not used. 
The monomer components contained in the polymers are preferably 
methacrylates, acrylamides and methacrylamides. Acrylamides and 
methacrylamides are most preferred. 
The number average molecular weight of the polymers which can be used in 
the present invention is preferably 5,000 to 150,000, and more preferably 
10,000 to 100,000. 
The water-insoluble polymer in the present invention is a polymer having a 
solubility of 3 g or less, preferably 1 g or less, to 100 g of distilled 
water (25.degree. C.). 
Specific examples of the polymers used in the present invention are shown 
below, but the scope of the present invention is not limited thereto. The 
copolymerization ratios of the copolymers in the specific examples shown 
below are molar ratios. 
P-1: Polymethyl methacrylate 
P-2: Polyethyl methacrylate 
P-3: Polyisopropyl methacrylate 
P-4: Polymethyl chloroacrylate 
P-5: Poly(2-tert-butylphenyl acrylate) 
P-6: Poly(4-tert-butylphenyl acrylate) 
P-7: Ethyl methacrylate-n-butyl acrylate copolymer (70:30) 
P-8: Methyl methacrylate-acrylonitrile copolymer (65:35) 
P-9: Methyl methacrylate-styrene copolymer (90:10) 
P-10: N-tert-Butylmethacrylamide-methyl methacrylateacrylic acid copolymer 
(60:30:10) 
P-11: Methyl methacrylate-styrene-vinylsulfonamide copolymer (70:20:10) 
P-12: Methyl methacrylate-cyclohexyl methacrylate copolymer (50:50) 
P-13: Methyl methacrylate-acrylic acid copolymer (95:5) 
P-14: Methyl methacrylate-n-butyl methacrylate copolymer (65:35) 
P-15: Methyl methacrylate-N-vinyl-2-pyrrolidone copolymer (90:10) 
P-16: Poly (N-sec-butylacrylamide) 
P-17: Poly (N-tert-butylacrylamide) 
P-18: Cyclohexyl methacrylate-methyl methacrylate copolymer (60:40) 
P-19: n-Butyl methacrylate-methyl methacrylate-acrylamide copolymer 
(20:70:10) 
P-20: Diacetoneacrylamide-methyl methacrylate copolymer (20:80) 
P-21: N-tert-Butylacrylamide-methyl methacrylate copolymer (40:60) 
P-22: Poly (N-n-butylacrylamide) 
P-23: tert-Butyl methacrylate-N-tert-butylacrylamide copolymer (50:50) 
P-24: tert-Butyl methacrylate-methyl methacrylate copolymer (70:30) 
P-25: Poly (N-tert-butylmethacrylamide) 
P-26: N-tert-Butylacrylamide-methyl methacrylate copolymer (60:40) 
P-27: Methyl methacrylate-acrylonitrile copolymer (70:30) 
P-28: Methyl methacrylate-styrene copolymer (75:25) 
P-29: Methyl methacrylate-hexyl methacrylate copolymer (70:30) 
P-30: Poly(4-biphenyl acrylate) 
P-31: Poly(2-chlorophenyl acrylate) 
P-32: Poly(4-chlorophenyl acrylate) 
P-33: Poly(pentachlorophenyl acrylate) 
P-34: Poly(4-ethoxycarbonylphenyl acrylate) 
P-35: Poly(4-methoxycarbonylphenyl acrylate) 
P-36: Poly(4-cyanophenyl acrylate) 
P-37: Poly(4-methoxyphenyl acrylate) 
P-38: Poly(3,5-dimethyladamantyl acrylate) 
P-39: Poly(3-dimethylaminophenyl acrylate) 
P-40: Poly(2-naphthyl acrylate) 
P-41: Poly(phenyl acrylate) 
P-42: Poly(N,N-dibutylacrylamide) 
P-43: Poly(isohexylacrylamide) 
P-44: Poly(isooctylacrylamide) 
P-45: Poly(N-methyl-N-phenylacrylamide) 
P-46: Poly(adamantyl methacrylate) 
P-47: Poly(sec-butyl methacrylate) 
P-48: N-tert-Butylacrylamide-acrylic acid copolymer (97:3) 
P-49: Poly(2-chloroethyl methacrylate) 
P-50: Poly(2-cyanoethyl methacrylate) 
P-51: Poly(2-cyanomethylphenyl methacrylate) 
P-52: Poly(4-cyanophenyl methacrylate) 
P-53: Poly(cyclohexyl methacrylate) 
P-54: Poly(2-hydroxypropyl methacrylate) 
P-55: Poly(4-methoxycarbonylphenyl methacrylate) 
P-56: Poly(3,5-dimethyladamantyl methacrylate) 
P-57: Poly(phenyl methacrylate) 
P-58: Poly(4-butoxycarbonylphenylmethacrylamide) 
P-59: Poly(4-carboxyphenylmethacrylamide) 
P-60: Poly(4-ethoxycarbonylphenylmethacrylamide) 
P-61: Poly(4-methoxycarbonylphenylmethacrylamide) 
P-62: Poly(cyclohexyl chloroacrylate) 
P-63: Poly(ethyl chloroacrylate) 
P-64: Poly(isobutyl chloroacrylate) 
P-65: Poly(isopropyl chloroacrylate) 
P-66: Poly(phenylacrylamide) 
P-67: Poly(cyclohexylacrylamide) 
P-68: Poly(phenylmethacrylamide) 
P-69: Poly(cyclohexylmethacrylamide) 
P-70: Poly(butylene adipate) 
In the present invention, the amount of the water-insoluble polymer used in 
the silver halide color photographic material is 0.02 to 2.0, and 
preferably 0.2 to 2.0, by weight ratio to the yellow coupler contained in 
a light-sensitive layer of the photographic material. In order to improve 
both the light fading and the color forming properties, however, it is 
more preferred that the weight ratio is 0.4 to 1.5. 
Methods for allowing the yellow couplers and the water-insoluble polymers 
of the present invention to be contained in the same layers are 
hereinafter described. 
In the present invention, it is preferred that the coupler and the 
water-insoluble polymer are allowed to coexist and be finely dispersed. 
More preferably, the coupler and the water-insoluble polymer exist in the 
same drop of oil. For example, a latex of the polymer can be impregnated 
with the coupler of the present invention by the so-called loadable latex 
method (see U.S. Pat. No. 4,203,716). The methods of using organic 
solvent-soluble polymers described in PCT International Publication No. 
WO88/00723 and U.S. Pat. No. 5,006,453 can be used as more preferable 
methods. Namely, the polymer, the high boiling organic solvent and the 
coupler of the present invention are completely dissolved in an auxiliary 
organic solvent, and the resulting solution is dispersed in a fine 
particle form in water, preferably in an aqueous solution of a hydrophilic 
colloid, more preferably in an aqueous solution of gelatin, by means of 
ultrasound or a colloid mill with the aid of a dispersing agent. 
The yellow couplers of the present invention are preferably used in 
combination with conventional antifading agents. Typical examples of such 
antifading agents include hydroquinones, 6-hydroxychromans, 
5-hydroxycoumarans, spirochromans, spiroindanes, p-alkoxyphenols, hindered 
phenols such as bisphenols, gallic acid derivatives, 
methylenedioxybenzenes, aminophenols, hindered amines and ether or ester 
derivatives obtained by silylating or alkylating phenolic hydroxyl groups 
of these compounds. 
Specific examples of the organic antifading agents are described in the 
following patent documents. 
The hydroquinones are described in U.S. Pat. Nos. 2,360,290, 2,418,613, 
2,675,314, 2,701,197, 2,728,659, 2,732,300, 2,735,765, 3,982,944, 
4,430,425, 2,710,801 and 2,816,028, and British Patent 1,363,921. The 
6-hydroxychromans, 5-hydroxycoumarans and spirochromans are described in 
U.S. Pat. Nos. 3,432,300, 3,573,050, 3,574,626, 3,698,909 and 3,764,337, 
and JP-A-52-152225. The spiroindanes are described in U.S. Pat. No. 
4,360,589. The p-alkoxyphenols are described in U.S. Pat. No. 2,735,765, 
British Patent 2,066,975, JP-A-59-10539 and JP-B-57-19765 (the term "JP-B" 
as used therein means an "examined Japanese patent publication"). 
The hindered phenols are described in U.S. Pat. Nos. 3,700,455 and 
4,228,235, JP-A-52-72225 and JP-B-52-6623. The gallic acid derivatives, 
the methylenedioxybenzenes and the aminophenols are each described in U.S. 
Pat. Nos. 3,457,079 and 4,332,886 and JP-B-56-21144. The hindered amines 
are described in U.S. Pat. Nos. 3,336,135 and 4,268,593, British Patents 
1,326,889, 1,354,313 and 1,410,846, JP-B-51-1420, JP-A-58-114036, 
JP-A-59-53846 and JP-A-59-78344. 
Of the above-described antifading agents, preferred are the hindered 
phenols represented by the following general formula (IV) and the 
bisphenols represented by the following general formula (V). 
##STR164## 
In general formula (IV), R.sup.11 represents a hydrogen atom, an alkyl 
group, an alkenyl group, an aryl group, an allyl group, an acyl group or a 
silyl group; and R.sup.12 and R.sup.13 are straight or branched alkyl 
groups of 3 to 8 carbon atoms, which are bonded preferably through 
secondary or tertiary carbon, more preferably through tertiary carbon. 
Specific examples of such alkyl groups include n-butyl, iso-propyl, 
tert-butyl and tert-amyl. Further, the alkyl groups may have appropriate 
substituents at any positions of the alkyl chains. R.sup.14 may be any 
group, as long as it is a monovalent organic group. Furthermore, R.sup.14 
may contain a hindered phenol or bisphenol moiety. 
##STR165## 
In general formula (V), R.sup.15 and R.sup.16 each independently represents 
a hydrogen atom, an alkyl group, an alkenyl group, an aryl group, an allyl 
group, an acyl group, a phosphonyl group, a phosphinyl group or a sulfonyl 
group, and R.sup.15 and R.sup.16 may combine through the above-described 
group to form a ring. R.sup.17 R.sup.18, R.sup.20 and R.sup.21 represent 
straight or branched alkyl groups of 1 to 8 carbon atoms. Specific 
examples include methyl, ethyl, n-propyl, iso-propyl, tert-butyl, 
tert-amyl, cyclohexyl, 1-methylcyclohexyl and cyclopentyl. The 
above-described alkyl groups may have appropriate substituents including 
halogen atoms. R.sup.19 is a hydrogen atom or a straight or branched alkyl 
group of 1 to 8 carbon atoms. Specific examples thereof include methyl, 
ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, iso-butyl, tert-butyl, 
tert-amyl and cyclohexyl. 
Specific examples of the hindered phenols and bisphenols preferably used in 
the present invention include, but are not limited to, the following 
compounds: 
##STR166## 
The silver halides used in the silver halide photographic materials of the 
present invention include silver chloride, silver chloroiodide, silver 
chloro(iodo)bromide, silver bromide and silver iodobromide. In particular, 
silver chlorobromide or silver chloride substantially free from silver 
iodide and containing 90 mol % or more (more preferably 98 mol % or more) 
of silver chloride is preferably used for rapid processing. 
In the photographic materials according to the present invention, it is 
preferred that the dyes decolorizable by processing (oxonol dyes among 
others) described in European Patent 0,337,490A2, pages 27 to 76 are added 
to hydrophilic colloidal layers so that the optical reflection density of 
the photographic materials at 680 nm reaches 0.70 or more, or that 12% by 
weight or more (more preferably 14% by weight or more) of titanium oxide 
surface-treated with dihydric to tetrahydric alcohols (for example, 
trimethylolethane) is added to water-resistant resin layers of supports, 
for an improvement in sharpness of images. 
In the photographic materials of the present invention, compounds for 
improving the keeping quality of color images described in European Patent 
0,277,589A2 are preferably used in combination with the couplers. In 
particular, they are preferably used in combination with pyrazoloazole 
couplers or pyrrolotriazole couplers. 
Namely, in order to prevent the production of stains caused by the 
formation of a forming dye due to reaction of a color developing agent 
remaining in a film or an oxidation product thereof with a coupler during 
storage after processing, and other side effects, it is preferred to use a 
compound (F) which is chemically bonded to an aromatic amine developing 
agent remaining after color development to form a chemically inactive, 
substantially colorless compound, and/or a compound (G) which is 
chemically bonded to an oxidation product of an aromatic amine color 
developing agent remaining after color development to form a chemically 
inactive, substantially colorless compound. 
Further, it is preferred that antifungal agents such as those described in 
JP-A-63-271247, be added to the photographic materials of the present 
invention to prevent various molds and bacteria from breeding in the 
hydrophilic colloidal layers and deteriorating images. 
A white polyester support or a support provided with a white 
pigment-containing layer on the side coated with silver halide emulsion 
layers, may be used as supports for the photographic material of the 
present invention. Furthermore, in order to improve sharpness, an 
antihalation layer is preferably formed on the side coated with silver 
halide emulsion layers, or on the back surface, of the support. In 
particular, it is preferred that the transmission density be established 
within the range of 0.35 to 0.8 so that the display can be appreciated 
with both reflected light and transmitted light. 
The photographic materials of the present invention may be exposed to 
visible light or infrared light. Exposing methods may be either low 
illuminance exposure or high illumination exposure for a short time. In 
particular, in the latter case, a laser scanning exposing method in which 
the exposing time is shorter than 10.sup.-4 second is preferred. 
In exposing, the band stop filter described in U.S. Pat. No. 4,880,726 is 
preferably used, whereby optical color mixing is eliminated and color 
reproducibility is markedly improved. 
It is preferred that the color photographic materials of the present 
invention be subjected to color development, bleach-fixing and washing (or 
stabilizing), after exposure. The bleaching and fixing may be carried out 
separately, not using the single bath process as described above. 
Silver halide emulsions, other materials such as additives and photographic 
constituent layers such as layer arrangements applied to the photographic 
materials of the present invention, and processing methods and additives 
for processing applied to treat the photographic materials, which are 
preferably used, are described in the following patents shown in Table 1, 
particularly in European Patent 0,355,660A2 (JP-A-2-139544). 
TABLE 1 
______________________________________ 
Photographic 
Constituents, EP0, 
etc. JP-A-62-215272 
JP-A-2-33144 
355,660A2 
______________________________________ 
Silver Halide 
Page 10, upper 
Page 28, Page 45, line 
Emulsions 
right column, 
upper right 53 to page 
line 6 to page 
column, line 
47, line 3; 
12, lower left 
16 to page page 47, line 
column, line 5; 
29, lower 20 to line 22 
page 12, lower 
right column, 
right column, 
line 11; page 
line 4 from the 
30, line 2 to 
bottom to page 
line 5 
13, upper left 
column, line 17 
Solvents for 
Page 12, lower 
-- -- 
Silver left column, 
Halides line 6 to line 
14; page 13, 
upper left 
column, line 
3 from the 
bottom to page 
18, lower left 
column, the 
last line 
Chemical Page 12, lower 
Page 29, lower 
Page 47, line 
Sensitizers 
left column, 
right column, 
4 to line 9 
line 3 from line 12 to 
the bottom to 
the last line 
lower right 
column, line 
5 from the 
bottom; page 
18, lower right 
column, line 1, 
to page 22, 
upper right 
column, line 9 
from the bottom 
Spectral Page 22, upper 
Page 30, upper 
Page 47, line 
Sensitizers 
right column, 
left column, 
10 to line 15 
(Spectrally 
line 8 from the 
line 1 to line 
Sensitizing 
bottom to page 
13 
Methods) 38, the last 
line 
Emulsion Page 39, upper 
Page 30, upper 
Page 47, line 
Stabilizers 
left column, 
left column, 
16 to line 19 
line 1 to page 
line 14 to 
72, upper right 
upper right 
column, the column, line 1 
last line 
Development 
Page 72, lower 
-- -- 
Accelerators 
left column, 
line 1 to page 
91, upper right 
column, line 3 
Color Page 91, upper 
Page 3, upper 
Page 4, line 
Couplers right column, 
right column, 
15 to line 27; 
(Cyan, line 4 to page 
line 14 to page 5, line 
Magenta, 121, upper page 18, upper 
30 to page 28, 
Yellow left column, 
left column, 
the last line; 
Couplers) 
line 6 the last line; 
page 45, line 
page 30, upper 
29 to line 31; 
right column, 
page 47, line 
line 6 to page 
23 to page 63, 
35, lower line 50 
right column, 
line 11 
Color Page 121, upper 
-- -- 
Development 
left column, 
Increasing 
line 7 to page 
Agents 125, upper right 
column, line 1 
Ultraviolet 
Page 125, upper 
Page 37, lower 
Page 65, line 
Absorbers 
right column, 
right column, 
22 to line 31 
line 2 to page 
line 14 to 
127, lower left 
page 38, upper 
column, the left column, 
last line line 11 
Antifading 
Page 127, lower 
Page 36, upper 
Page 4, line 
Agents right column, 
right column, 
30 to page 5, 
(Image Stabi- 
line 1 to page 
line 12 to line 23; page 
lizers) 137, lower left 
page 37, upper 
29, line 1 to 
column, line 8 
left column, 
page 45, line 
line 19 25; page 45, 
line 33 to 
line 40; page 
65, line 2 to 
line 21 
High Boiling 
Page 137, lower 
Page 35, lower 
Page 64, line 
and/or Low 
left column, 
right column, 
1 to line 51 
Boiling line 9 to page 
line 14 to 
Organic 144, upper page 36, upper 
Solvents right column, 
left column, 
the last line 
line 4 from 
the bottom 
Dispersing 
Page 144, lower 
Page 27, lower 
Page 63, line 
Methods of 
left column, 
right column, 
51 to page 
Photographic 
line 1 to page 
line 10 to 64, line 56 
Additives 
146, upper page 28, upper 
right column, 
left column, 
line 7 the last line; 
page 35, lower 
right column, 
line 12 to page 
36, upper right 
column, line 7 
Hardeners 
Page 146, upper 
-- -- 
right column, 
line 8 to page 
155, lower left 
column, line 4 
Developing 
Page 155, lower 
-- -- 
Agent Pre- 
left column, 
cursors line 5 to lower 
right column, 
line 2 
Development 
Page 155, lower 
-- -- 
Restrainer- 
right column, 
Releasing 
line 3 to line 
Compounds 
9 
Supports Page 155, lower 
Page 38, upper 
Page 66, line 
right column, 
right column, 
29 to page 
line 19 to page 
line 18 to 67, line 13 
156, upper left 
page 39, upper 
column, line 14 
left column, 
line 3 
Photographic 
Page 156, upper 
Page 28, upper 
Page 45, line 
Material left column, 
right column, 
41 to line 52 
Layer line 15 to page 
line 1 to line 
Constitution 
156, lower 15 
right column, 
line 14 
Dyes Page 156, lower 
Page 38, upper 
Page 66, line 
right column, 
left column, 
18 to line 22 
line 15 to page 
line 12 to 
184, lower upper right 
right column, 
column, line 
the last line 
7 
Color Mixing 
Page 185, upper 
Page 36, upper 
Page 64, line 
Inhibitors 
left column, 
right column, 
57 to page 
line 1 to page 
line 8 to line 
65, line 1 
188, lower 11 
right column, 
line 3 
Gradation 
Page 188, lower 
-- -- 
Modifiers 
right column, 
line 4 to line 
8 
Stain Page 188, lower 
Page 37, upper 
Page 65, line 
Inhibitors 
right column, 
left column, 
32 to page 
line 9 to page 
the last line 
66, line 17 
193, lower to lower right 
right column, 
column, line 
line 10 13 
Surfactants 
Page 201, lower 
Page 18, upper 
-- 
left column, 
right column, 
line 1 to page 
line 1 to page 
210, upper 24, lower 
right column, 
right column, 
the last line 
the last line; 
page 27, lower 
left column, 
line 10 from 
the bottom to 
lower right 
column, line 9 
Fluorine- 
Page 210, lower 
Page 25, upper 
-- 
Containing 
right column, 
left column, 
Compounds 
line 1 to page 
line 1 to page 
(Antistatic 
222, lower left 
27, lower 
Agents, Coat- 
column, line 5 
right column, 
ing Aids, line 9 
Lubricants, 
Adhesion 
Inhibitors) 
Binders Page 222, lower 
Page 38, upper 
Page 66, line 
(Hydrophilic 
left column, 
right column, 
23 to line 28 
Colloids) 
line 6 to page 
line 8 to line 
225, upper left 
18 
column, the 
last line 
Tackifiers 
Page 225, upper 
-- -- 
right column, 
line 1 to page 
227, upper 
right column, 
line 2 
Antistatic 
Page 227, upper 
-- -- 
Agents right column, 
line 3 to page 
230, upper left 
column, line 1 
Polymer Page 230, upper 
-- -- 
Latices left column, 
line 2 to page 
239, the last 
line 
Matting Page 240, upper 
-- -- 
Agents left column, 
line 1 to upper 
right column, 
the last line 
______________________________________ 
Note: The cited portions of JP-A-62-215272 include the contents of the 
amendment dated Mar. 16, 1987 which is given in the end of the 
publication. In addition, of the above-described color couplers, as yellow 
couplers, so-called short wave type yellow couplers are also preferably 
used, and are described in JP-A-63-231451, JP-A-63-123047, JP-A-63-241547, 
JP-A-l-173499, JP-A-1-213648 and JP-A-1-250944. 
Cyan couplers preferably used include the diphenylimidazole cyan couplers 
described in JP-A-2-33144, the 3-hydroxypyridine cyan couplers described 
in European Patent 0,333,185A2 including the coupler made 2-equivalent by 
giving a chlorine eliminatable group to a 4-equivalent coupler of coupler 
(42), and couplers (6) and (9), which are particularly preferred, and the 
cyclic active methylene cyan couplers described in JP-A-64-32260 including 
couplers (3), (8) and (34) which are particularly preferred. 
As a method for processing the silver halide color photographic materials 
using the high silver chloride emulsions containing at least 90 mol % of 
silver chloride, the method described on page 27, upper left column, to 
page 34, upper right column, of JP-A-2-207250 is preferably applied. 
The present invention will be further illustrated in greater detail with 
reference to the following examples, which are, however, not to be 
construed as limiting the invention. 
The structures of high boiling organic solvents used in the following 
examples, other than those compounds represented by general formulae (S-1) 
to (S-5), are as follows: 
##STR167## 
EXAMPLE 1 
Using a triacetyl cellulose support having an under coat, monolayer 
photographic material 101 for evaluation having the following layer 
constitution, was prepared. 
Preparation of Emulsion Layer Coating Solution 
To 1.85 mmol of a coupler, 10 cc of ethyl acetate and 40% by weight (to the 
coupler) of trioctyl phosphate (a high boiling organic solvent, 
hereinafter also referred to as "an oil"), were added to dissolve the 
coupler. The resulting solution was dispersed by emulsification in 33 g of 
a 14% aqueous solution of gelatin containing 3 cc of a 10% solution of 
sodium dodecylbenzenesulfonate. On the other hand, a silver chlorobromide 
emulsion (silver bromide: 70 mol %) was sulfur sensitized and mixed -with 
the above-described emulsified product to prepare a coating solution so as 
to give the following composition. As a hardener, sodium salt of 
1-oxy-3,5-dichloro-s-triazine was used. 
Layer Constitution 
The layer constitution of the sample used in this experiment is shown 
below. Numerals indicate coated weights (g/m.sup.2). 
Support 
Triacetyl Cellulose Support 
______________________________________ 
Emulsion Layer 
Silver Chlorobromide (described above) 
4.0 mmol 
Coupler (see Table 2) 1.0 mmol 
Solvent (see Table 2) (40% by weight 
of coupler) 
Gelatin 5.2 g 
Protective Layer 
Gelatin 1.3 g 
Acrylic Modified Copolymer of Polyvinyl 
0.17 g 
Alcohol (degree of modification: 17%) 
Liquid Paraffin 0.03 g 
______________________________________ 
The above-described photographic material was subjected to imagewise 
exposure using an optical wedge, and thereafter processed according to the 
following processing stages. 
______________________________________ 
Processing Stages 
Temperature 
Time 
Processing Stage (.degree.C.) 
(min) 
______________________________________ 
Color Development 
33 2 
Bleach-Fixing 33 1.5 
Washing 33 3 
______________________________________ 
Composition of Processing Solutions 
Color Developing Solution 
Distilled Water 800 ml 
Triethanolamine 8.1 g 
Diethylhydroxylamine 4.2 g 
Potassium Bromide 0.6 g 
Sodium Hydrogencarbonate 3.9 g 
Sodium Sulfite 0.13 g 
N-Ethyl-N-(.beta.-methanesulfonamido- 
5.0 g 
ethyl)-3-methyl-4-aminoaniline 
Sulfate 
Potassium Carbonate 18.7 g 
Water to make 1000 ml 
pH 10.25 
Bleach-Fixing Solution 
Distilled Water 400 ml 
Ammonium Thiosulfate (700 g/liter) 
150 ml 
Sodium Sulfate 18.0 g 
Ethylenediaminetetraacetic Acid 
55.0 g 
(III) Ammonium 
Sodium Ethylenediaminetetraacetate 
5.0 g 
Water to make 1000 ml 
pH 6.7 
______________________________________ 
Then, samples 102 to 165 were prepared in the same manner as with sample 
101 with the exception that couplers were changed so as to become 
equimolar to sample 101, and the kinds and the amounts of oils used (the 
weight ratios of the oils to the couplers) were changed as shown in Table 
2. These samples were exposed, followed by processing, in the same manner 
as the above-described sample 101. 
For the processed samples, the yellow color forming density was measured 
through a blue color filter to prepare sensitometry curves. The maximum 
color forming density (Dmax) was read from these curves. The Dmax value 
mainly depends on the molecular extinction coefficient and coupling 
activity of the yellow coupler. Accordingly, a coupler showing an increase 
in this value can be said to be an excellent coupler high in color forming 
property. 
Then, in order to evaluate the color image fastness of the above-described 
samples against light, the samples were irradiated with Xe light of 
100,000 luxes (by an intermittent irradiation process of 3-hour 
irradiation/1-hour putting out lights) for 14 days, and then the density 
was measured again. The density of residual color images at Dmax portions 
was determined by percentage as evaluated values, which are shown in Table 
2. 
TABLE 2 
__________________________________________________________________________ 
Fading 
Color Form- 
Xe, 14 days 
Oil ing Property 
(residual rate) 
Sample 
Coupler 
Kind 
Amount 
(Dmax) (%) Remark 
__________________________________________________________________________ 
101 ExY-1 
S-110 
0.4 1.28 74 Comparison 
102 ExY-1 
S-110 
0.6 1.43 67 Comparison 
103 ExY-1 
S-110 
1.0 1.51 53 Comparison 
104 ExY-1 
S-102 
0.4 1.27 83 Comparison 
105 ExY-1 
S-102 
0.6 1.48 79 Comparison 
106 ExY-1 
S-102 
1.0 1.52 74 Comparison 
107 ExY-1 
S-201 
0.4 1.46 80 Comparison 
108 ExY-1 
S-201 
0.6 1.51 73 Comparison 
109 ExY-1 
S-201 
1.0 1.53 62 Comparison 
110 ExY-1 
S-502 
0.4 1.35 75 Comparison 
111 ExY-1 
S-502 
0.6 1.42 69 Comparison 
112 ExY-1 
S-502 
1.0 1.50 56 Comparison 
113 (2) S-110 
0.4 1.94 41 Comparison 
114 (2) S-110 
0.6 1.97 75 Invention 
115 (2) S-110 
0.8 1.99 82 Invention 
116 (2) S-110 
1.0 2.00 87 Invention 
117 (2) S-110 
2.0 2.01 91 Invention 
118 (2) S-102 
0.4 1.93 35 Comparison 
119 (2) S-102 
0.6 1.97 71 Invention 
120 (2) S-102 
0.8 2.02 78 Invention 
121 (2) S-102 
1.0 2.04 83 Invention 
122 (2) S-102 
2.0 2.03 86 Invention 
123 (2) S-201 
0.4 1.97 32 Comparison 
124 (2) S-201 
0.6 2.02 67 Invention 
125 (2) S-201 
0.8 2.04 74 Invention 
126 (2) S-201 
1.0 2.04 79 Invention 
127 (2) S-201 
2.0 2.03 83 Invention 
128 (2) S-502 
0.4 1.96 34 Comparison 
129 (2) S-502 
0.6 1.98 69 Invention 
130 (2) S-502 
0.8 1.99 75 Invention 
131 (2) S-502 
1.0 2.00 81 Invention 
132 (2) S-502 
2.0 2.00 85 Invention 
133 (2) S-407 
0.4 1.92 35 Comparison 
134 (2) S-407 
0.6 1.95 70 Invention 
135 (2) S-407 
1.0 1.96 76 Invention 
136 (2) S-301 
0.4 1.94 32 Comparison 
137 (2) S-301 
0.6 1.98 68 Invention 
138 (2) S-301 
1.0 1.99 75 Invention 
139 (1) S-111 
0.4 2.08 37 Comparison 
140 (1) S-111 
0.6 2.09 72 Invention 
141 (1) S-111 
1.0 2.10 84 Invention 
142 (1) S-104 
0.4 2.12 32 Comparison 
143 (1) S-104 
0.6 2.13 69 Invention 
144 (1) S-104 
1.0 2.13 76 Invention 
145 (1) S-205 
0.4 2.14 30 Comparison 
146 (1) S-205 
0.6 2.14 66 Invention 
147 (1) S-205 
1.0 2.14 73 Invention 
148 (29) S-111 
0.4 2.16 46 Comparison 
149 (29) S-111 
1.0 2.18 90 Invention 
150 (16) S-111 
0.4 2.04 43 Comparison 
151 (16) S-111 
1.0 2.07 88 Invention 
152 (25) S-111 
0.4 1.93 45 Comparison 
153 (25) S-111 
1.0 1.95 89 Invention 
154 (8) S-111 
0.4 2.04 48 Comparison 
155 (8) S-111 
1.0 2.06 91 Invention 
156 (37) S-111 
0.4 1.96 28 Comparison 
157 (37) S-111 
1.0 2.02 70 Invention 
158 (2) S-601 
0.4 1.84 43 Comparison 
159 (2) S-601 
1.0 1.87 73 Invention 
160 (2) S-602 
0.4 1.88 18 Comparison 
161 (2) S-602 
1.0 1.90 57 Invention 
162 (2) S-125 
0.4 1.98 35 Comparison 
163 (2) S-125 
1.0 2.04 80 Invention 
164 (2) S-130 
0.4 2.01 39 Comparison 
165 (2) S-130 
1.0 2.05 78 Invention 
__________________________________________________________________________ 
ExY-1 
##STR168## 
##STR169## 
The results shown in Table 2 reveal that coupler Ex-Y for comparison 
has a tendency to be improved in color forming property as the amounts of 
the high boiling organic solvents used increase, but the light fastness 
decreases. Thus, the conventional acylacetanilide-type couplers including 
the pivaloyl-type yellow couplers tend to be improved in light fastness 
In contrast, the results shown in Table 2 reveal that the couplers of the 
present invention exhibit color forming density as high as 1.4 to 1.5 
times that of ExY-1, regardless of the amounts of the high boiling organic 
solvents used. 
Further, the color image fastness against light is significantly improved 
when the amounts of the high boiling organic solvents used (the weight 
ratios of the solvents to the couplers) are 0.6 or more. This fact can not 
be anticipated at all from the light fading behavior of the 
acylacetanilide-type yellow couplers described above. 
As is described above, when the high boiling organic solvents are used in 
weight ratios to the couplers of 0.6 or more with the yellow couplers of 
the present invention, it becomes possible to realize the high color 
forming property and the excellent light fastness at the same time. 
EXAMPLE 2 
Using a triacetyl cellulose support having an under coat, monolayer 
photographic material 201 was prepared for evaluation having the following 
layer constitution. 
Preparation of Emulsion Layer Coating Solution 
To 1.85 mmol of a coupler, 10 cc of ethyl acetate, and 40% by weight (to 
the coupler) of tricresyl phosphate (a high boiling organic solvent), were 
added to dissolve the coupler. The resulting solution was dispersed by 
emulsification in 33 g of a 14% aqueous solution of gelatin containing 3 
cc of a 10% solution of sodium dodecylbenzene-sulfonate. On the other 
hand, a silver chlorobromide emulsion was prepared; cubic, a 3:7 mixture 
(silver molar ratio) of a large-sized emulsion having a mean grain size of 
0.88 .mu.m and a small-sized emulsion having a mean grain size of 0.70 
.mu.m, coefficients of variation in grain size distribution for the 
respective emulsions being 0.08 and 0.10, each emulsion comprising silver 
halide grains in which 0.3 mol % of silver bromide is localized on part of 
the surface of each grain and the remainder is silver chloride. Each of 
blue sensitizing dyes A and B shown below was added to this emulsion in an 
amount of 2.0.times.10.sup.-4 mol per mol of silver for the large-sized 
emulsion, and in an amount of 2.5.times.10.sup.-4 mol per mol of silver 
for the small-sized emulsion. Chemical sensitization of this emulsion was 
carried out by adding a sulfur sensitizing agent and a gold sensitizing 
agent. This emulsion and the above-described emulsified product were mixed 
with each other to prepare a coating solution so as to give the following 
composition. As a hardener, sodium salt of 1-oxy-3,5-dichloro-s-triazine 
was used. 
Layer Constitution 
The layer constitution of the sample used in this experiment is shown 
below. Numerals indicate coated weights (g/m.sup.2). 
Support 
Triacetyl Cellulose Support 
______________________________________ 
Emulsion Layer 
Silver Chlorobromide (described above) 
3.0 mmol 
Coupler (see Table 3) 1.0 mmol 
Solvent (see Table 3) (40% by weight 
of coupler) 
Gelatin 5.5 g 
Protective Layer 
Gelatin 1.5 g 
Acrylic Modified Copolymer of Polyvinyl 
0.15 g 
Alcohol (degree of modification: 17%) 
Liquid Paraffin 0.03 g 
______________________________________ 
Blue-Sensitive Emulsion Layer 
Sensitizing Dye A 
##STR170## 
and 
Sensitizing Dye B 
##STR171## 
ExY-2 
##STR172## 
##STR173## 
The above-described photographic material was subjected to exposure 
through an optical wedge, and thereafter processed according to the 
following stages. 
______________________________________ 
Processing Stages 
Temperature 
Time 
Processing Stage (.degree.C.) 
(sec) 
______________________________________ 
Color Development 
35 45 
Bleaching-Fixing 35 45 
Stabilizing (1) 35 20 
Stabilizing (2) 35 20 
Stabilizing (3) 35 20 
Stabilizing (4) 35 20 
Drying 80 60 
______________________________________ 
Four-tank countercurrent system from stabilizing (4) to stabilizing (1) 
was employed. 
The composition of each processing solution was as follows: 
______________________________________ 
Color Developing Solution 
Water 800 ml 
1-Hydroxyethylidene-1,1-diphosphonic 
0.8 ml 
Acid (60%) 
Triethanolamine 8.0 g 
Sodium Chloride 1.4 g 
Potassium Bromide 0.03 g 
N,N-Diethylhydroxylamine 4.6 g 
Potassium Carbonate 27 g 
Sodium Sulfite 0.1 g 
N-Ethyl-N-(.beta.-methanesulfonamidoethyl)- 
4.5 g 
3-methyl-4-aminoaniline 3/2 Sulfate 
Monohydrate 
Lithium Sulfate (anhydrous) 
2.7 g 
Fluorescent Brightener 2.0 g 
(4,4'-diaminostilbene type) 
Water to make 1000 ml 
pH (by adding potassium hydroxide) 
10.25 
Bleach-Fixing Solution 
Water 400 ml 
Ammonium Thiosulfate (700 g/liter) 
100 ml 
Sodium Sulfite 18 g 
Ethylenediaminetetraacetic Acid 
55 g 
Fe(III) Ammonium 
Disodium Ethylenediaminetetraacetate 
3 g 
Glacial Acetic Acid 9 g 
Water to make 1000 ml 
pH 5.4 
Stabilizing Solution 
Benzoisothiazoline-3-one 0.02 g 
Polyvinylpyrrolidone 0.05 g 
Water to make 1000 ml 
pH 7.0 
______________________________________ 
Then, samples 202 to 269 were prepared in the same manner as sample 201, 
with the exception that the types of couplers, and the types and amounts 
of high boiling organic solvents (the weight ratios of the solvents to the 
couplers) were changed as shown in Table 3. When the couplers of the 
present invention were used, the total amounts applied were reduced to 70% 
by weight of that of sample 201. These samples were also exposed, followed 
by processing, in the same manner as with the above-described sample 201. 
For the processed samples, the yellow color forming density and the magenta 
component density in yellow were measured through a blue color filter and 
a green color filter, respectively, to prepare respective sensitometry 
curves. The magenta component at a yellow color forming density of 1.5, 
which is determined by the following equation from these curves, was taken 
as a measure for indicating hue, D.sub.G /D.sub.B. 
Magenta Component=100.times.Magenta Density/Yellow Color Forming Density 
The magenta component on yellow color forming is decreased, as this value 
is lowered. A lowered value shows that hue is excellent. 
The color image fastness against light was evaluated the same manner as 
with Example 1, with the proviso that the residual rate was indicated by a 
value at an initial density of 1.5. 
TABLE 3 
__________________________________________________________________________ 
High Boiling Organic Solvent 
Fading 
Sample 
Coupler 
Kind 
Dielectric Const. 
Amount 
Hue (DG/DB) 
(residual rate) 
Remark 
__________________________________________________________________________ 
201 ExY-1 
S-102 
7.33 0.4 7.2 70 Comparison 
202 ExY-1 
S-102 
7.33 1.0 7.0 59 Comparison 
203 ExY-1 
S-124 
5.08 0.4 6.9 65 Comparison 
204 ExY-1 
S-124 
5.08 1.0 6.7 48 Comparison 
205 ExY-1 
S-110 
4.80 0.4 6.7 58 Comparison 
206 ExY-1 
S-110 
4.80 1.0 6.3 42 Comparison 
207 ExY-1 
S-111 
4.46 0.4 6.7 69 Comparison 
208 ExY-1 
S-111 
4.46 1.0 6.4 60 Comparison 
209 ExY-1 
S-201 
6.45 0.4 7.0 62 Comparison 
210 ExY-1 
S-201 
6.45 1.0 6.8 45 Comparison 
211 ExY-1 
S-203 
5.18 0.4 6.9 65 Comparison 
212 ExY-1 
S-203 
5.18 1.0 6.6 61 Comparison 
213 ExY-2 
S-102 
7.33 0.4 5.1 55 Comparison 
214 ExY-2 
S-102 
7.33 1.0 4.8 40 Comparison 
215 ExY-2 
S-110 
4.80 0.4 4.7 50 Comparison 
216 ExY-2 
S-110 
4.80 1.0 4.4 36 Comparison 
217 ExY-2 
S-201 
6.45 0.4 4.9 52 Comparison 
218 ExY-2 
S-201 
6.45 1.0 4.7 39 Comparison 
219 (1) S-110 
4.80 0.4 5.7 30 Comparison 
220 (1) S-110 
4.80 0.6 4.5 59 Invention 
221 (1) S-110 
4.80 0.8 4.0 72 Invention 
222 (1) S-110 
4.80 1.0 3.7 80 Invention 
223 (1) S-110 
4.80 1.5 3.5 84 Invention 
224 (1) S-110 
4.80 2.0 3.3 87 Invention 
225 (1) S-201 
6.45 0.4 6.3 25 Comparison 
226 (1) S-201 
6.45 0.6 5.8 53 Invention 
227 (1) S-201 
6.45 0.8 5.5 62 Invention 
228 (1) S-201 
6.45 1.0 5.3 70 Invention 
229 (1) S-201 
6.45 2.0 5.0 78 Invention 
230 (1) S-601 
13.45 0.4 7.4 42 Comparison 
231 (1) S-601 
13.45 0.6 7.2 62 Invention 
232 (1) S-601 
13.45 1.0 6.9 70 Invention 
233 (1) S-601 
13.45 2.0 6.7 73 Invention 
234 (1) S-602 
2.06 0.4 6.9 22 Comparison 
235 (1) S-602 
2.06 0.6 5.6 48 Invention 
236 (1) S-602 
2.06 1.0 5.2 57 Invention 
237 (1) S-603 
10.6 0.4 7.2 47 Comparison 
238 (1) S-603 
10.6 0.6 7.0 65 Invention 
239 (1) S-603 
10.6 1.0 6.8 71 Invention 
240 (2) S-101 
7.68 0.4 6.6 29 Comparison 
241 (2) S-101 
7.68 1.0 5.8 78 Invention 
242 (2) S-102 
7.33 0.4 6.4 31 Comparison 
243 (2) S-102 
7.33 1.0 5.6 82 Invention 
244 (2) S-104 
6.64 0.4 6.3 37 Comparison 
245 (2) S-104 
6.64 1.0 5.4 86 Invention 
246 (2) S-124 
5.08 0.4 6.2 35 Comparison 
247 (2) S-124 
5.08 1.0 5.0 84 Invention 
248 (2) S-109 
5.86 0.4 6.2 32 Comparison 
249 (2) S-109 
5.86 1.0 4.5 81 Invention 
250 (2) S-110 
4.80 0.4 5.8 35 Comparison 
251 (2) S-110 
4.80 1.0 4.0 86 Invention 
252 (2) S-111 
4.46 0.4 5.9 37 Comparison 
253 (2) S-111 
4.46 1.0 4.1 89 Invention 
254 (2) S-112 
3.87 0.4 5.8 38 Comparison 
255 (2) S-112 
3.87 1.0 4.0 85 Invention 
256 (2) S-201 
6.45 0.4 6.6 28 Comparison 
257 (2) S-201 
6.45 1.0 5.8 75 Invention 
258 (2) S-209 
6.45 0.4 6.7 32 Comparison 
259 (2) S-209 
6.45 1.0 5.8 80 Invention 
260 (2) S-203 
5.18 0.4 6.2 30 Comparison 
261 (2) S-203 
5.18 1.0 5.0 77 Invention 
262 (2) S-206 
4.17 0.4 6.1 33 Comparison 
263 (2) S-206 
4.17 1.0 4.7 79 Invention 
264 (2) S-301 
4.49 0.4 6.1 30 Comparison 
265 (2) S-301 
4.49 1.0 4.6 76 Invention 
266 (2) S-502 
3.96 0.4 6.0 31 Comparison 
267 (2) S-502 
3.96 1.0 4.2 75 Invention 
268 (2) S-407 
3.84 0.4 6.0 33 Comparison 
269 (2) S-407 
3.84 1.0 4.2 74 Invention 
__________________________________________________________________________ 
The results shown in Table 3 reveal that coupler ExY-1 for comparison has a 
high D.sub.G /D.sub.B value and has undesirable hue. This value does not 
largely vary, even if the amounts of the high boiling organic solvents are 
changed. 
On the other hand, the results shown in Table 3 reveal that coupler ExY-2 
for comparison shows a relatively low D.sub.G /D.sub.B value, even when 
the amounts of the high boiling organic solvents used are small, and is 
superior to coupler ExY-1 in hue. However, even this coupler did not show 
the tendency of the hue to be further largely improved by increasing the 
amounts of the high boiling organic solvents. 
Further, the results reveal that ExY-2 is inferior to ExY-1 in light 
fastness. Furthermore, it was observed that the couplers were both 
deteriorated in light fastness by increasing the amount of the high 
boiling organic solvent. 
In contrast, with respect to the yellow couplers of the present invention, 
a greater effect of improving the hue (a drop in D.sub.G /D.sub.B value) 
was observed by increasing the amounts of the high boiling organic 
solvents used. This tendency is pronounced at the high boiling organic 
solvents having a dielectric constant of 6.0 or less (for example, S-110, 
S-124, S-ill, S-203 and S-206). 
Further, this tendency is particularly pronounced with alkyl phosphates 
(for example, S-110 and S-111), which can be said to be the high boiling 
organic solvents preferable to improve the hue of the couplers of the 
present invention. 
Furthermore, for any of the high boiling organic solvents, an improvement 
in light fastness is observed by increasing the amounts of the high 
boiling organic solvents used. Of the high boiling organic solvents, the 
solvents represented by general formulae (S-1) to (S-5) are highly 
effective. 
EXAMPLE 3 
A paper support, both sides of which were laminated with polyethylene, was 
subjected to corona discharge treatment and then provided with a gelatin 
underlayer containing sodium dodecylbenzenesulfonate. Various photographic 
constituent layers were further applied thereto. Thus, a multilayer color 
photographic paper sample 300 having the following layer constitution was 
prepared. Coating solutions were prepared as follows: 
Preparation of Coating Solution for First Layer 
132.0 g of yellow coupler (ExY), 15.0 g of color image stabilizer (Cpd-1), 
7.5 g of color image stabilizer (Cpd-2) and 16.0 g of color image 
stabilizer (Cpd-3), were dissolved in 25 g of solvent (Solv-1), 25 g of 
solvent (Solv-2) and 180 cc of ethyl acetate. The resulting solution was 
emulsified and dispersed in 1000 g of a 10% aqueous solution of gelatin 
containing 60 cc of 10% sodium dodecylbenzenesulfonate and 10 g of citric 
acid, to prepare an emulsified dispersion A. This emulsified dispersion A 
and the silver chlorobromide emulsion prepared in Example 2 were mixed 
with each other to prepare a coating solution for a first layer so as to 
have the composition shown below. The amount of emulsion applied indicates 
a coated weight converted to silver. 
Coating solutions for the second to seventh layers were prepared in the 
same manner as to the coating solution for the first layer. As a gelatin 
hardener for each layer, the sodium salt of 1-oxy-3,5-dichloro-s-triazine 
was used. 
Cpd-14 and Cpd-15 were added to each layer to total amounts of 25.0 
mg/m.sup.2 and 50.0 mg/m.sup.2, respectively. 
In silver chlorobromide emulsions of other respective light-sensitive 
emulsion layers, the following color sensitizing dyes were used. 
##STR174## 
4.0.times.10.sup.-4 mol per mol of silver halide for a large-sized 
emulsion, and 5.6'10.sup.-4 mol per mol of silver halide for a small-sized 
emulsion. 
##STR175## 
7.0.times.10.sup.-5 mol per mol of silver halide for a large-sized 
emulsion, and 1.0.times.10.sup.-4 mol per mol of silver halide for a 
small-sized emulsion. 
##STR176## 
0.9.times.10.sup.-4 mol per mol of silver halide for a large-sized 
emulsion, and 1.1.times.10.sup.-4 mol per mol of silver halide for a 
small-sized emulsion. 
The following compound was further added in an amount of 
2.6.times.10.sup.-3 mol per mol of silver halide: 
##STR177## 
Further, 1-(5-methylureidophenyl)-5-mercaptotetrazole was added to the 
blue-sensitive emulsion layer, the green-sensitive emulsion layer and the 
red-sensitive emulsion layer in amounts of 8.5.times.10.sup.-5 mol, 
7.7.times.10.sup.-4 mol and 2.5.times.10.sup.-4 mol per mol of silver 
halide, respectively. 
Furthermore, 4-hydroxy-6-methyl-l,3,3a,7-tetraazaindene was added to the 
blue-sensitive emulsion layer and the green-sensitive emulsion layer in 
amounts of 1.times.10.sup.-4 mol and 2.times.10.sup.-4 mol per mol of 
silver halide, respectively. 
The following dyes were added to the emulsion layers for prevention of 
irradiation. The numerical values in parentheses indicate coated weights. 
##STR178## 
Layer Constitution 
The composition of each layer is hereinafter shown. The numerals indicate 
coated weights (g/m.sup.2). For the silver halide emulsions, the numerals 
indicate coated weights converted to silver. 
Support 
The support was paper laminated with polyethylene (polyethylene on the side 
of the first layer containing a white pigment (TiO.sub.2) and a bluing dye 
(ultramarine)). 
______________________________________ 
First Layer (Blue-Sensitive Emulsion Layer) 
Silver Chlorobromide Emulsion 
0.27 
Described Above 
Gelatin 1.36 
Yellow Coupler (ExY) 0.68 
Color Image Stabilizer (Cpd-1) 
0.08 
Color Image Stabilizer (Cpd-2) 
0.04 
Color Image Stabilizer (Cpd-3) 
0.08 
Solvent (Solv-1) 0.13 
Solvent (Solv-2) 0.13 
Second Layer (Color Mixing Preventing Layer) 
Gelatin 1.00 
Color Mixing Inhibitor (Cpd-4) 
0.08 
Solvent (Solv-7) 0.03 
Solvent (Solv-2) 0.25 
Solvent (Solv-3) 0.25 
Third Layer (Green-Sensitive Emulsion Layer) 
Silver Chlorobromide Emulsion 
0.13 
Cubic, a 1:3 mixture (Ag molar ratio) of 
a large-sized emulsion having a mean grain 
size of 0.55 .mu.m and a small-sized emulsion 
having a mean grain size of 0.39 .mu.m, 
coefficients of variation in grain 
size distribution being 0.1 and 0.08, 
respectively, each emulsion containing 
silver halide in which 0.8 mol % of AgBr 
is localized on part of the surface of 
each grain and the remainder being silver 
chloride. 
Gelatin 1.45 
Magenta Coupler (ExM) 0.16 
Color Image Stabilizer (Cpd-5) 
0.15 
Color Image Stabilizer (Cpd-2) 
0.03 
Color Image Stabilizer (Cpd-6) 
0.01 
Color Image Stabilizer (Cpd-7) 
0.01 
Color Image Stabilizer (Cpd-8) 
0.08 
Solvent (Solv-3) 0.50 
Solvent (Solv-4) 0.15 
Solvent (Solv-5) 0.15 
Fourth Layer (Color Mixing Preventing Layer) 
Gelatin 0.70 
Color Mixing Inhibitor (Cpd-4) 
0.05 
Solvent (Solv-7) 0.02 
Solvent (Solv-2) 0.18 
Solvent (Solv-3) 0.18 
Fifth Layer (Red-Sensitive Emulsion Layer) 
Silver Chlorobromide Emulsion 
0.20 
Cubic, a 1:4 mixture (Ag molar ratio) of 
a large-sized emulsion having a mean grain 
size of 0.50 .mu.m and a small-sized emulsion 
having a mean grain size of 0.41 .mu.m, 
coefficients of variation in grain 
size distribution being 0.09 and 0.11, 
respectively, each emulsion containing 
silver halide in which 0.8 mol % of AgBr 
is localized on part of the surface of 
each grain and the remainder being silver 
chloride. 
Gelatin 0.85 
Cyan Coupler (ExC) 0.33 
Ultraviolet Light Absorber (UV-2) 
0.18 
Color Image Stabilizer (Cpd-9) 
0.01 
Color Image Stabilizer (Cpd-10) 
0.01 
Color Image Stabilizer (Cpd-11) 
0.01 
Solvent (Solv-6) 0.22 
Color Image Stabilizer (Cpd-8) 
0.01 
Color Image Stabilizer (Cpd-6) 
0.01 
Solvent (Solv-1) 0.01 
Color Image Stabilizer (Cpd-1) 
0.33 
Sixth Layer (Ultraviolet Light Absorbing Layer) 
Gelatin 0.55 
Ultraviolet Light Absorber (UV-1) 
0.38 
Color Image Stabilizer (Cpd-12) 
0.15 
Color Image Stabilizer (Cpd-5) 
0.02 
Seventh Layer (Protective Layer) 
Gelatin 1.13 
Acrylic Modified Copolymer of Polyvinyl 
0.05 
Alcohol (degree of modification: 17%) 
Liquid paraffin 0.02 
Color Image Stabilizer (Cpd-13) 
0.01 
______________________________________ 
##STR179## 
The above-described photographic material 300 was subjected to imagewise 
exposure using an optical wedge for three-color separation sensitometry. 
Then, continuous processing (running test) was carried out according to 
the following processing stages using a paper processor until the 
replenishment rate of the processing solutions reached twice the tank 
capacity of color development. 
______________________________________ 
Replenish-* 
Tank 
Processing 
Temperature 
Time ment Rate 
Capacity 
Stage (.degree.C.) 
(sec) (ml) (liter) 
______________________________________ 
Color 35 45 161 10 
Development 
Bleach-Fixing 
35 45 218 10 
Rinsing (1) 
35 30 -- 5 
Rinsing (2) 
35 30 -- 5 
Rinsing (3) 
35 30 360 5 
Drying 80 60 
______________________________________ 
*Replenishment rate per m.sup.2 of lightsensitive material 
Three-tank countercurrent system from rinsing (3) to rinsing (1) was 
employed. 
The composition of each processing solution was as follows: 
______________________________________ 
Tank Re- 
Solution 
plenisher 
______________________________________ 
Color Developing Solution 
Water 800 ml 800 ml 
Ethylenediaminetetraacetic 
3.0 g 3.0 g 
Acid 
Disodium 4,5-Dihydroxy- 
0.5 g 0.5 g 
benzene-1,3-disulfonate 
Triethanolamine 12.0 g 12.0 g 
Potassium Chloride 2.5 g -- 
Potassium Bromide 0.01 g -- 
Potassium Carbonate 27.0 g 27.0 g 
Fluorescent Brightener 1.0 g 2.5 g 
(WHITEX 4, Sumitomo Chemical 
Co., Ltd.) 
Sodium Sulfite 0.1 g 0.2 g 
Disodium-N,N-bis(sulfonate- 
5.0 g 8.0 g 
ethyl) hydroxylamine 
N-Ethyl-N-(.beta.-methanesulfon- 
5.0 g 7.1 g 
amidoethyl)-3-methyl-4- 
aminoaniline.3/2 Sulfate. 
Monohydrate 
Water to make 1000 ml 1000 ml 
pH (25.degree. C., with potassium 
10.05 10.45 
hydroxide and sulfuric acid) 
Bleach-Fixing Solution (tank solution and 
replenisher being the same) 
Water 600 ml 
Ammonium Thiosulfate (700 g/liter) 
100 ml 
Ammonium Sulfite 40 g 
Ethylenediaminetetraacetic Acid 
55 g 
Fe(III) Ammonium 
Iron Ethylenediaminetetraacetate 
5 g 
Ammonium Bromide 40 g 
Nitric Acid (67%) 30 g 
Water to make 1000 ml 
pH (25.degree. C., with acetic acid and 
5.8 
aqueous ammonia) 
Rinsing Solution (tank solution and 
replenisher being the same) 
Chlorinated Sodium Isocyanurate 
0.02 g 
Deionized Water (electric conduc- 
1000 ml 
tivity: 5 .mu.s/cm or less) 
pH 6.5 
______________________________________ 
Then, samples 301 to 385 were prepared in the same manner as with sample 
300, with the exception that couplers, polymers (the amounts used are 
indicated by the percentages by weight to the couplers), and high boiling 
organic solvents (the amounts used are indicated by the weight ratios to 
the couplers) shown in Table 4 were substituted for yellow coupler (ExY), 
color image stabilizer (Cpd-1) and solvent (Solv-2), respectively. 
Three sheets of each sample were exposed using an optical wedge for 
three-color separation sensitometry, followed by processing using 
processing solutions brought to a running state by use of the 
above-described sample 300. After processing, the yellow color forming 
density was measured for each sample through a blue color filter to 
prepare a sensitometry curve. 
The yellow color forming density (Dmax) of each sample at exposure at which 
sample 300 gives a density of 2.20 (corresponding to the maximum color 
forming density), was read from the sensitometry curve, and the average 
values of three sheets are shown in Table 4 as evaluated values. 
Then, one of the above-described sheets was irradiated with Xe light of 
100,000 luxes (by intermittent irradiation of 3 hours in light/1 hour in 
the dark) for 28 days, and then the yellow density was measured again to 
determine the residual rate of color images. For the residual rate of 
color images, the residual rate at an initial density of 1.5 was indicated 
by percentage as an evaluated value of light fastness. 
Further, another one of the above-described sheets was stored at 80.degree. 
C. at a relative humidity of 70% for 28 days, and subsequently the 
residual rate of color images was determined in the same manner as 
described above as an evaluated value of dark fastness. 
These evaluated values are shown in Table 4. 
TABLE 4 
__________________________________________________________________________ 
Color 
Light Fading 
Dark Fading 
High Boiling Forming 
Xe 80.degree. C., 70% 
Solvent Polymer Property 
28 days 
28 days 
Sample 
Coupler 
Kind 
Amount 
Kind 
Amount (%) 
Dmax (%) (%) Remark 
__________________________________________________________________________ 
301 ExY-1 
S-201 
0.4 -- -- 2.17 65 60 Comparison 
302 ExY-1 
S-201 
0.6 -- -- 2.22 61 62 Comparison 
303 ExY-1 
S-201 
1.0 -- -- 2.29 57 65 Comparison 
304 ExY-1 
S-201 
0.4 P-17 
10 2.08 76 62 Comparison 
305 ExY-1 
S-201 
0.4 P-17 
20 1.68 80 63 Comparison 
306 ExY-1 
S-201 
0.6 P-17 
10 2.14 71 64 Comparison 
307 ExY-1 
S-201 
0.6 P-17 
20 1.75 75 64 Comparison 
308 ExY-1 
S-201 
1.0 P-17 
10 2.21 67 67 Comparison 
309 ExY-1 
S-201 
1.0 P-17 
20 2.08 71 68 Comparison 
310 ExY-1 
S-201 
1.0 P-17 
30 1.92 74 68 Comparison 
311 ExY-1 
S-201 
1.0 P-17 
50 1.74 78 69 Comparison 
312 ExY-2 
S-110 
0.4 -- -- 2.04 65 65 Comparison 
313 ExY-2 
S-110 
1.0 -- -- 2.32 52 68 Comparison 
314 ExY-2 
S-110 
0.4 P-17 
10 1.87 73 68 Comparison 
315 ExY-2 
S-110 
0.4 P-17 
20 1.58 77 69 Comparison 
316 ExY-2 
S-110 
1.0 P-17 
10 2.24 64 70 Comparison 
317 ExY-2 
S-110 
1.0 P-17 
20 1.73 68 71 Comparison 
318 (2) S-201 
0.4 -- -- 2.25 48 87 Comparison 
319 (2) S-201 
0.6 -- -- 2.27 67 90 Invention 
320 (2) S-201 
1.0 -- -- 2.28 75 92 Invention 
321 (2) S-201 
0.4 P-17 
10 2.24 55 89 Comparison 
322 (2) S-201 
0.4 P-17 
20 2.24 57 89 Comparison 
323 (2) S-201 
0.4 P-17 
50 2.17 60 90 Comparison 
324 (2) S-201 
0.6 P-17 
10 2.26 74 92 Invention 
325 (2) S-201 
0.6 P-17 
20 2.25 83 92 Invention 
326 (2) S-201 
0.6 P-17 
50 2.21 88 93 Invention 
327 (2) S-201 
1.0 P-17 
20 2.27 88 94 Invention 
328 (2) S-201 
1.0 P-17 
50 2.27 90 95 Invention 
329 (2) S-201 
1.0 P-17 
100 2.24 92 96 Invention 
330 (2) S-201 
0.4 P-2 
20 2.24 56 89 Comparison 
331 (2) S-201 
1.0 P-2 
20 2.26 85 94 Invention 
332 (2) S-201 
0.4 P-70 
20 2.23 54 87 Comparison 
333 (2) S-201 
1.0 P-70 
20 2.25 82 92 Invention 
334 (2) S-110 
0.4 -- -- 2.23 55 90 Comparison 
335 (2) S-110 
0.6 -- -- 2.25 72 92 Invention 
336 (2) S-110 
1.0 -- -- 2.25 81 93 Invention 
337 (2) S-110 
0.4 P-17 
10 2.23 62 92 Comparison 
338 (2) S-110 
0.4 P-17 
20 2.23 64 93 Comparison 
339 (2) S-110 
0.4 P-17 
50 2.21 66 94 Comparison 
340 (2) S-110 
1.0 P-17 
20 2.25 86 94 Invention 
341 (2) S-110 
1.0 P-17 
50 2.25 90 95 Invention 
342 (2) S-110 
1.0 P-17 
100 2.24 95 97 Invention 
343 (2) S-102 
0.4 -- -- 2.25 53 88 Comparison 
344 (2) S-102 
0.6 -- -- 2.27 70 91 Invention 
345 (2) S-102 
1.0 2.28 78 92 Invention 
346 (2) S-102 
0.4 P-67 
10 2.25 59 90 Comparison 
347 (2) S-102 
0.4 P-67 
20 2.24 62 91 Comparison 
348 (2) S-102 
0.4 P-67 
50 2.22 64 91 Comparison 
349 (2) S-102 
1.0 P-67 
20 2.28 82 93 Invention 
350 (2) S-102 
1.0 P-67 
50 2.27 88 93 Invention 
351 (2) S-102 
1.0 P-67 
100 2.25 94 94 Invention 
352 (1) S-111 
0.4 -- -- 2.19 49 88 Comparison 
353 (1) S-111 
0.6 -- -- 2.21 68 90 Invention 
354 (1) S-111 
1.0 -- -- 2.22 79 91 Invention 
355 (1) S-111 
0.4 P-17 
20 2.18 56 89 Comparison 
356 (1) S-111 
0.6 P-17 
20 2.20 75 90 Invention 
357 (1) S-111 
1.0 P-17 
20 2.22 86 92 Invention 
358 (1) S-203 
0.4 -- -- 2.21 50 90 Comparison 
359 (1) S-203 
0.6 -- -- 2.23 69 93 Invention 
360 (1) S-203 
1.0 -- -- 2.24 81 95 Invention 
361 (1) S-203 
0.4 P-67 
20 2.20 58 93 Comparison 
362 (1) S-203 
0.6 P-67 
20 2.23 78 95 Invention 
363 (1) S-203 
1.0 P-67 
20 2.24 89 97 Invention 
364 (1) S-203 
1.0 P-67 
50 2.21 92 98 Invention 
365 (29) S-110 
0.4 -- -- 2.24 45 85 Comparison 
366 (29) S-110 
0.6 -- -- 2.27 68 90 Invention 
367 (29) S-110 
1.0 -- -- 2.28 80 92 Invention 
368 (29) S-110 
0.4 P-17 
20 2.20 52 89 Comparison 
369 (29) S-110 
0.6 P-17 
20 2.25 74 92 Invention 
370 (29) S-110 
1.0 P-17 
20 2.27 86 94 Invention 
371 (29) S-110 
1.0 P-17 
50 2.24 91 96 Invention 
372 (8) S-110 
0.4 -- -- 2.18 43 88 Comparison 
373 (8) S-110 
0.6 -- -- 2.20 69 90 Invention 
374 (8) S-110 
1.0 -- -- 2.21 82 90 Invention 
375 (8) S-110 
0.4 P-17 
20 2.16 53 91 Comparison 
376 (8) S-110 
0.6 P-17 
20 2.20 75 93 Invention 
377 (8) S-110 
1.0 P-17 
20 2.21 84 94 Invention 
378 (8) S-110 
2.0 P-17 
100 2.21 93 96 Invention 
379 (15) S-110 
0.4 -- -- 2.08 35 91 Comparison 
380 (15) S-110 
0.6 -- -- 2.14 62 93 Invention 
381 (15) S-110 
1.0 -- -- 2.18 85 94 Invention 
382 (15) S-110 
0.4 P-17 
20 2.01 48 92 Comparison 
383 (15) S-110 
0.6 P-17 
20 2.10 75 95 Invention 
384 (15) S-110 
1.0 P-17 
20 2.17 91 95 Invention 
385 (15) S-110 
2.0 P-17 
50 2.16 94 96 Invention 
__________________________________________________________________________ 
The results shown in Table 4 reveal that the yellow couplers of the present 
invention are significantly improved in light fastness when the high 
boiling organic solvents are used in weight ratios to the couplers of 0.6 
or more, as shown in Examples 1 and 2. 
Even when each of the polymers is added to coupler ExY-1 for comparison, 
the light fastness is improved. However, although this effect increases 
with increasing the amount of the polymer added, a reduction in color 
forming property is induced at the same time. Accordingly, when the 
couplers for comparison are used, the amount of the polymer which can be 
added for an improvement in light fading has a limitation. 
On the other hand, the light fastness is also improved by adding the 
polymers to the couplers of the present invention. When the high boiling 
organic solvents are used in amounts to the couplers of less than 0.6, the 
level of the light fastness of the coupler for comparison is not reached. 
However, when the high boiling organic solvents are used in weight ratios 
to the couplers of 0.6 or more, a light fastness equivalent to or higher 
than that of the coupler for comparison is attained. Further increases in 
the amounts of the polymers cause the realization of a higher light 
fastness without lowering the color forming property. 
Further, the same samples as described above were processed by use of the 
above-described processing stages, and running processing was continued 
until the replenishment rate of the developing solution reached 5 times 
the tank capacity, followed by evaluations in the same manner as to those 
described above. The results thereof revealed that the samples of the 
present invention had a lower drop in the maximum color forming density 
than the samples for comparison. This shows that the samples of the 
present invention are excellent because of little processing dependency. 
Furthermore, the results shown in Table 4 reveal that significant 
improvements in color image fastness in the dark also become possible by 
using the yellow couplers of the present invention. 
EXAMPLE 4 
Samples were prepared in the same manner as with Example 3, with the 
exception that HP-5, BP-14 or BP-15 was substituted for color image 
stabilizer (Cpd-2) in the blue-sensitive emulsion layer of each sample of 
Example 3. These samples were also evaluated in the same manner as with 
Example 3. 
Also in this case, the couplers of the present invention were confirmed to 
show a particularly high light fastness when the high boiling organic 
solvents were used in weight ratios to the couplers of 0.6 or more. 
As has been described in the foregoing Examples 1 to 4, it becomes possible 
to provide the photographic materials excellent in color reproducibility, 
color forming property, color image fastness and processing dependency by 
using the couplers of the present invention with the high boiling organic 
solvents which are used in weight ratios to the couplers of 0.6 or more. 
In particular, the color image fastness can be more improved by using the 
polymers in amounts of 20% by weight or more based on the couplers. 
While the invention has been described in detail and with reference to 
specific embodiments thereof, it will be apparent to one skilled in the 
art that various changes and modifications can be made therein without 
departing from the spirit and scope thereof.