Silver halide photographic light-sensitive material

A silver halide photographic light-sensitive material and a process for preparing the same are disclosed wherein an oil-soluble photographic additive and, in particular, a cyan coupler is dissolved in an epoxy compound of the formula (I): ##STR1## wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4 each represents an alkyl group or substituted alkyl group containing 1 to 40 carbon atoms, an alkoxycarbonyl group or substituted alkoxycarbonyl group containing 1 to 40 carbon atoms, or a hydrogen atom, provided that R.sub.1, R.sub.2, R.sub.3 and R.sub.4 do not represent hydrogen atoms at the same time and that the sum of the number of carbon atoms of R.sub.1, R.sub.2, R.sub.3 and R.sub.4 is 8 to 60, and R.sub.1, R.sub.2, R.sub.3 and R.sub.4 may be the same or different and may combine to form a ring; or in an epoxy compound formed by linking two compounds of said formula (I) which may be the same or different through any of R.sub.1 to R.sub.4 or the ring formed by R.sub.1 to R.sub.4.

BACKGROUND OF THE INVENTION 
1. Field of the Invention 
The present invention relates to a silver halide photographic 
light-sensitive material and, more particularly, it relates to a silver 
halide photographic light-sensitive material containing oil-soluble 
photographic additives dispersed in a hydrophilic organic colloid layer 
using an epoxy compound or compounds. 
2. Description of the Prior Art 
Oil-soluble photographic additives (for example, oil-soluble couplers, 
antioxidants for preventing color fog or color mixing, fading-preventing 
agents (e.g., alkylhydroquinones, alkylphenols, chromans, coumarones, 
etc.), hardening agents, oil-soluble filter dyes, oil-soluble U.V. 
absorbing agents, DIR compounds (e.g., DIR hydroquinones, uncolored DIR 
compounds, etc.), developing agents, color developers, and DRR compounds 
(e.g., DDR couplers, etc.)) have heretofore been used by dissolving them 
in a suitable high-boiling organic solvent, dispersing the solution in a 
hydrophilic organic colloid, in particular, a gelatin solution, in the 
presence of a surface active agent and incorporating them into a 
hydrophilic organic colloid layer (e.g., a light-sensitive emulsion layer, 
a filter layer, a backing layer, an antihalation layer, an interlayer, a 
protective layer, etc.). As the high-boiling organic solvent, phthalic 
ester compounds and phosphoric ester compounds are particularly used. 
In particular, most of the solvents for photographic additives (e.g., 
oil-soluble incorporated type couplers) used in the manufacture of color 
and black-and-white photographic light-sensitive materials are of these 
types. Examples thereof are described in U.S. Pat. Nos. 2,322,027, 
2,533,514, 3,287,134, 3,748,141, 3,779,765, West German Pat. No. 
1,152,610, British Pat. No. 1,272,561, West German Patent Application 
(OLS) No. 2,629,842, etc. The high boiling solvents of phthalic ester 
compounds and phosphoric ester compounds have often been used for their 
coupler-dispersing ability, their affinity for the gelatin colloid layer, 
their influence on the stability of colored images, their influence on the 
hue of colored images, their chemical stability in a light-sensitive 
material, their inexpensiveness, their availability, etc. 
However, such high boiling organic solvents are not totally satisfactory 
from the standpoint of their ability to disperse oil-soluble photographic 
additives, their affinity for a hydrophilic organic colloid layer, their 
influence on photographic properties, their chemical stability in a 
light-sensitive material, and the like. For example, some high boiling 
organic solvents exert detrimental influences on the photographic 
properties (e.g., on the stability of the color images obtained by 
dispersing a photographic coupler, and on the development-processing of a 
coupler-containing light-sensitive material), although some exhibit good 
photographic additive dispersing property, and some have reverse 
properties. 
In particular, there have been no high boiling organic solvents for 
oil-soluble photographic additives which provide a good, fast cyan color 
image resistant to heat and humidity and show good dispersing property. 
SUMMARY OF THE INVENTION 
A principal object of the present invention is to provide a color 
light-sensitive material, wherein an oilsoluble cyan coupler is dispersed 
in a stable state in a hydrophilic colloid. 
Another object of the present invention is to provide color images with 
high fastness to heat and humidity. 
Still a further object of the present invention is to provide a means for 
dispersing oil-soluble photographic additives in general into a 
hydrophilic colloid. 
A further object of the present invention is to provide a high boiling 
solvent for oil-soluble photographic additives including oil-soluble cyan 
couplers which can be used alone or in combination with the high boiling 
organic solvents conventionally used for this purpose. 
A still further object of the present invention is to provide a high 
boiling solvent with good dispersing ability which does not interfere with 
the formation of a fast image. 
These and other objects have been attained by dissolving a coupler capable 
of oxidatively coupling with a developing agent to form a cyan color image 
in an epoxy compound represented by general formula (I) or in an epoxy 
compound wherein two compounds of the formula (I) which may be the same or 
different are linked together at the R.sub.1 to R.sub.4 groups or the 
rings formed thereby, and dispersing it in a hydrophilic organic colloid: 
##STR2## 
In the above formula, R.sub.1, R.sub.2, R.sub.3 and R.sub.4 each represents 
a straight chain, branched chain or cyclic alkyl group having 1 to 40 
carbon atoms (for example, butyl, octyl, dodecyl, isostearyl, cyclohexyl, 
etc.); a substituted alkyl group containing 1 to 40 carbon atoms 
(including the substituents), wherein the alkyl moiety is a straight 
chain, branched chain or cyclic alkyl group and the substituent is an 
alkoxycarbonyl group having 2 to 23 carbon atoms (for example, 
butyloxycarbonyl, 2-ethylhexyloxycarbonyl, dodecyloxycarbonyl, 
hexadecyloxycarbonyl, cyclohexyloxycarbonyl, etc.), an alkylcarbonyloxy 
group having 2 to 23 carbon atoms (for example, acetoxy, pivaloyloxy, 
dodecylcarbonyloxy, hexadecylcarbonyloxy, etc.), an arylcarbonyloxy group 
having 7 to 23 carbon atoms (for example, benzoyloxy, p-methylbenzoyloxy, 
m-nitrobenzoyloxy, 2,4-dichlorobenzoyloxy, etc.), an alkoxy group having 1 
to 22 carbon atoms (for example, ethyloxy, 2-methoxyethoxy, dodecyloxy, 
etc.) or an aryloxy group having 6 to 22 carbon atoms (for example, 
phenoxy, p-methoxyphenoxy, 2,4-di-t-butylphenoxy, m-pentadecylphenoxy, 
etc.); an alkoxycarbonyl group containing 1 to 40 carbon atoms wherein the 
alkoxy moiety is a straight chain, branched chain or cyclic alkoxy group 
(for example, butyloxycarbonyl, 2-ethylhexyloxycarbonyl, decyloxycarbonyl, 
hexadecyloxycarbonyl, cyclohexyloxycarbonyl, etc.); a substituted 
alkoxycarbonyl group having 1 to 40 carbon atoms (including substituents) 
wherein the alkoxy moiety is a straight chain, branched chain or cyclic 
alkoxy group and the substituent is the same as described above for the 
alkyl group; or a hydrogen atom; provided that all of R.sub.1, R.sub.2, 
R.sub.3 and R.sub.4 do not represent hydrogen atoms at the same time and 
the sum of the number of carbon atoms of R.sub.1, R.sub.2, R.sub.3 and 
R.sub.4 is 8 to 60, preferably 8 to 45. Further, R.sub.1, R.sub.2, R.sub.3 
and R.sub.4 may be the same or different from each other and may form a 
ring. The ring may be a 5- or 6-membered ring (for example, cyclohexane, 
cycloheptane) and substituted with a carboxylic acid ester group (for 
example, a butyloxycarbonyl group, an octyloxycarbonyl group, a 
hexadecyloxycarbonyl group, etc.) or an alkyl group (for example, an ethyl 
group, etc.). The R groups forming the ring may be on the same or 
different carbon atoms. 
Of the compounds represented by the general formula (I), particularly 
preferable compounds are those represented by the general formula (II): 
##STR3## 
wherein R.sub.1, R.sub.2 and R.sub.3 are the same as defined in the 
general formula (I), provided that at least one of R.sub.1, R.sub.2 and 
R.sub.3 is an alkyl group substituted by an alkoxycarbonyl group, an 
aryloxycarbonyl group or an aryloxy group having 8 to 40 carbon atoms 
(including carbon atoms of the substituents) and the sum of the number of 
carbon atoms of R.sub.1, R.sub.2 and R.sub.3 is 8 to 60, preferably 8 to 
45. Further, R.sub.1 and R.sub.3 may combine to form a ring as defined 
above. 
Specific examples of the epoxy compounds to be used in the present 
invention are illustrated below, which, however, are only illustrative and 
are not intended to limit the present invention. 
##STR4## 
As the cyan couplers to be used in the present invention, any so-called 
oil-soluble cyan coupler can be used. Examples thereof will be described 
below. 
As the cyan couplers, phenolic compounds, naphtholic compounds, etc., can 
be used. Specific examples thereof are oil-soluble couplers selected from 
those described in U.S. Pat. Nos. 2,369,929, 2,434,272, 2,474,293, 
2,521,908, 2,895,826, 3,034,892, 3,311,476, 3,458,315, 3,476,563, 
3,583,971, 3,591,383, 3,767,411, West German Patent Application (OLS) Nos. 
2,414,830, 2,454,329, Japanese Patent Application (OPI) NOs. 59838/73 (The 
term "OPI" as used herein refers to a "published unexamined Japanese 
patent application"), 26034/76, 5055/73, 146828/76, U.S. Pat. No. 
4,004,929, etc. 
Further, of the cyan color image-forming couplers, it is particularly 
advantageous to use those represented by the following general formula 
(III) since they are particularly remarkably improved in dye fastness. 
##STR5## 
In the above formula, R.sub.5 represents a straight chain, branched chain 
or cyclic alkyl group having 1 to 22 carbon atoms (for example, ethyl, 
butyl, dodecyl, isostearyl, cyclohexyl, etc.); a substituted alkyl group 
wherein the alkyl moiety is a straight chain, branched chain or cyclic 
alkyl group having 1 to 22 carbon atoms and the substituent is a halogen 
atom, an ether group, an acylamino group, a carbamoyl group, a sulfonamide 
group or a sulfamoyl group (for example, trichloromethyl, 
heptafluoropropyl, 1(2',4'-di-t-pentylphenoxy)propyl, 
4-decanoylaminophenoxymethyl, 1-(4-hexadecanesulfonylaminophenoxy)propyl, 
3-(m-pentadecylphenoxy)propyl, etc.); or a substituted or unsubstituted 
aryl group having 6 to 22 carbon atoms wherein the substituent may be a 
halogen atom or an aryloxy group (for example, phenyl, p-chlorophenyl, 
p-phenoxyphenyl, etc.). R.sub.6 represents a straight chain or branched 
chain alkyl group having 1 to 22 carbon atoms (for example, methyl, ethyl, 
isopropyl, t-butyl, pentadecyl, etc.); a substituted alkyl group wherein 
the alkyl moiety is a straight chain or branched chain alkyl group having 
1 to 22 carbon atoms and the substituent is a halogen atom, an ether group 
or a thioether group (for example, chloromethyl, ethoxymethyl, 
p-chlorophenylthiomethyl, etc.); an acylamino group represented by the 
formula R.sub.5 CONH- group (in this case, the R.sub.6 group and the 
R.sub.5 CONH- group may be the same or different from each other); or a 
hydrogen atom. It is necessary that at least one of R.sub.5 and R.sub.6 
represents a so-called ballast group containing 10 to 22 carbon atoms. X 
represents a group capable of being eliminated upon oxidative coupling 
with a developing agent (a so-called coupling-off group). The coupling-off 
group determines the equivalency of the coupler (that is, whether the 
coupler is two-equivalent coupler or fourequivalent coupler). Further, the 
coupling-off group can improve the reactivity of the coupler, inhibit 
development and accelerate bleaching. Representative examples of X include 
a hydrogen atom, a halogen atom, an alkoxy group, an aryloxy group, an 
arylazo group, a thioether group and a heterocyclic ring such as an 
oxazolyl, a diazolyl, a triazolyl or a tetrazolyl ring. The most preferred 
coupling-off groups for X are a hydrogen atom and a halogen atom (for 
example, chlorine, fluorine, bromine, etc.). Y represents a hydrogen atom 
or a halogen atom (for example, fluorine, chlorine, bromine, iodine, 
etc.). 
As the cyan couplers used in accordance with the present invention there 
are, for example, also those described in U.S. Pat. Nos. 2,367,531, 
2,423,452, 3,222,176, 3,647,452, 3,652,286, 3,737,318, 3,758,308, 
3,779,763, 3,864,366, 3,998,642, 4,009,035, etc. 
Specific examples of the cyan couplers to be used in the present invention 
will be illustrated below, which are offered only for illustration. The 
present invention is not limited to these uses alone. 
##STR6## 
The epoxy compounds to be used in the present invention are characterized 
by their boiling point which are higher than 200.degree. C. under 
atmospheric pressure. 
The epoxy compounds of the general formula (I) to be used in the present 
invention can generally be obtained by oxidizing an olefinic double bond 
with hydrogen peroxide as described in T. W. Findlay et al., J. Amer. 
Chem. Soc., 67, 412 (1945); R. J. Gall et al., Ind. Eng. Chem., 47, 147 
(1955); U.S. Pat. No. 2,485,160; F. P. Greenspan et al., J. Amer. Oil 
Chem. Soc., 33, 391 (1956); and R. M. Brice et al., Ind. Eng. Chem., 50, 
868, 871 and 873 (1958). In general, such epoxy compounds are commercially 
available as plasticizers for polymers and show particularly excellent 
properties when used as a high boiling organic solvent in photographic 
lightsensitive materials. Examples of commercially available epoxy 
compounds are: Unox 201 (Compound 12) and Unox 269 (Compound 17) which are 
products of Union Carbide Corp.; Sansosizer E-4030 (Compound 1) and 
Sansosizer EPE (Compound 11) which are products of New Japan Chemical Co., 
Ltd.; and Newsizer 540 (Compound 1), Newsizer 560 (Compound 2) and 
Newsizer 580 (Compound 4) which are products of Nippon Oils & Fats Co., 
Ltd. 
The epoxy compounds of the general formula (I) may be used independently as 
a high boiling organic solvent by dissolving therein the oil-soluble 
photographic additives or may be used in combination with other known high 
boiling organic solvents. 
The amount (weight ratio) of epoxy compounds represented by the general 
formula (I) to be used is about 0.05 to 20, preferably about 0.1 to 10, 
based on the amount of epoxy compound to the amount of oil-soluble 
photographic additive and/or cyan coupler. 
As the oil-soluble photographic additives other than the cyan coupler which 
can be advantageously mixed in accordance with the present invention, 
there are all photographic additives which have so far been dispersed in a 
hydrophilic organic colloid layer using known high boiling organic 
solvents. As the typical oil-soluble photographic additives, there are 
illustrated: oil-soluble photographic yellow couplers, oil-soluble 
photographic magenta couplers, antioxidants and color fade-preventing 
agents capable of preventing color fog or fading of colored images (e.g., 
alkylhydroquinones, alkylphenols, chromans, coumarones, phosphites, etc.), 
hardeners, oil-soluble filter dyes capable of selectively absorbing 
visible light or ultraviolet rays, oil-soluble ultraviolet ray-absorbing 
agents, fluorescent brightening agents, DIR compounds (e.g., DIR 
hydroquinones, DIR coupling compounds, etc.), developing agents, DIR 
couplers, DRR compounds, color developers, etc. 
As stated above, the high boiling epoxy compound solvents to be used in the 
present invention can exhibit the same properties as a conventional high 
boiling organic solvents when used alone and, in addition, they can be 
used together with other known high boiling solvents for photographic 
additives. As such known high boiling organic solvents, there are 
illustrated, for example, those described in U.S. Pat. Nos. 2,322,037, 
2,533,514, 2,835,579, Japanese Patent Publication No. 23233/71, U.S. Pat. 
No. 3,287,134, British Pat. No. 958,441, Belgian Pat. No. 768,585, British 
Pat. Nos. 1,222,753 and 1,501,233, U.S. Pat. No. 3,936,303, Japanese 
Patent Application (OPI) Nos. 26037/76 and 82078/75, U.S. Pat. Nos. 
2,353,262, 2,852,383, 3,554,755, 3,676,137, 3,767,142, 3,700,454, 
3,748,141, 3,837,863 and 4,004,928, German Patent Applicatio (OLS) No. 
2,538,889, Japanese Patent Application (OPI) No. 27921/76, Japanese Patent 
Publication Nos. 28693/77 and 29461/74, U.S. Pat. Nos. 3,936,303 and 
3,748,141 etc. As the high boiling organic solvents which can be used more 
preferably, there are illustrated esters (e.g., phthalic acid esters, 
phosphoric acid esters, citric acid esters, benzoic acid esters, fatty 
acid esters, carbonic acid esters, etc.), amides (e.g., fatty acid amides, 
sulfonamides, etc.), ethers (e.g., allyl ethers, etc.), alcohols, 
paraffins, etc. Particularly preferable high boiling organic solvents are, 
for example, phthalic esters (e.g., dibutyl phthalate, dihexyl phthalate, 
diheptyl phthalate, dioctyl phthalate, dinonyl phthalate, didecyl 
phthalate, butylphthalylbutyl glycolate, dibutyl monochlorophthalate, 
etc.), phosphoric acid esters (e.g., tricresyl phosphate, trixylenyl 
phosphate, tris(isopropylphenyl) phosphate, tributyl phosphate, trihexyl 
phosphate, trioctyl phosphate, trinonyl phosphate, tridecyl phosphate, 
trioleyl phosphate, tris(butoxyethyl) phosphate, tris(chloroethyl) 
phosphate, tris(dichloropropyl) phosphate, etc.), citric acid esters 
(e.g., o-acetyltriethyl(or butyl, hexyl, octyl, nonyl or decyl) citrate, 
etc.), benzoic acid esters (e.g., butyl (or hexyl, heptyl, oxtyl, nonyl, 
decyl, dodecyl, tridecyl, tetradecyl, hexadecyl, octadecyl, oleyl, etc.) 
benzoate, pentyl o-methylbenzoate, decyl p-methylbenzoate, octyl 
o-chlorobenzoate, lauryl p-chlorobenzoate, propyl 2,4-dichlorobenzoate, 
octyl 2,4-dichlorobenzoate, stearyl 2,4-dichlorobenzoate, oleyl 
2,4-dichlorobenzoate, octyl p-methoxybenzoate, etc.), fatty acid esters 
(e.g., hexadecyl myristate, dibutoxyethyl succinate, dioctyl adipate, 
dioctyl azelate, decamethylene-1,10-diol diacetate, triacetin, tributyrin, 
benzyl caprate, pentaerythritol tetracapronate, isosorbide dicaprylate, 
etc.), amides (e.g., N,N-dimethyllauroamide, N,N-diethylcaprylamide, 
N-butylbenzenesulfonamide, etc.), trioctyl trimellitate, chlorinated 
paraffin, etc. 
The epoxy compounds of the present invention may be used together with 
substantially water-insoluble low boiling auxiliary solvents (e.g., methyl 
acetate, ethyl acetate, butyl acetate, etc.), or water-soluble organic 
auxiliary solvents (e.g., methyl isobutyl ketone, .beta.-ethoxyethyl 
acetate, methyl carbitol, methyl cellosolve, dipropylene glycol 
dimethylformamide, dioxane, etc.). Such low boiling auxiliary solvents are 
described in, for example, U.S. Pat. Nos. 2,801,170, 2,801,171, 2,949,360 
and 3,835,579. These auxiliary solvents may be removed by washing with 
water as described in U.S. Pat. Nos. 2,801,171, 2,949,360 and 3,396,027, 
or may be removed by vaporizing as described in U.S. Pat. Nos. 2,322,027, 
2,801,171, West German Patent Application (OLS) No. 2,045,464, etc. 
The epoxy compounds of the present invention are used alone or in 
combinations of two or more compounds, and photographic additives such as 
couplers, antioxidants, filter dyes, etc., are dissolved therein, followed 
by dispersing the solution in an aqueous solution of hydrophilic colloid 
(in particular, gelatin). In this case, it is particularly preferable to 
use a single epoxy compound or a mixture of epoxy compounds in further 
combination with an auxiliary solvent. 
The method of dispersion is described in, for example, U.S. Pat. Nos. 
2,304,939, 2,322,027, 2,801,170, 2,801,171, 2,949,360, etc. 
As the dispersing aids, usually employed are anionic surface active agents 
(e.g., sodium alkylbenzenesulfonate, sodium dioctylsulfosuccinate, sodium 
dodecylsulfate, sodium alkylnaphthalenesulfonate, Fischer type couplers, 
etc.), amphoteric surface active agents (e.g., 
N-tetradecyl-N,N-dipolyethylene-.alpha.-betaine, etc.) and nonionic 
surface active agents (e.g., sorbitan monolaurate, etc.). 
The hydrophilic organic colloid layer in accordance with the present 
invention is a photographic layer using, as a binder, a hydrophilic 
organic colloid (for example, gelatin (very often used), cellulose 
derivatives, alginates, hydrophilic synthetic polymers (e.g., polyvinyl 
alcohol, polyvinyl pyrrolidone, polystyrenesulfonic acid, styrenesulfonic 
acid copolymers, maleic acid copolymers, acrylic acid copolymers, 
methacrylic acid copolymers, itaconic acid copolymers, etc.), modified 
gelatin (e.g., phthaloylated gelatin, etc.), and the like; these 
hydrophilic organic colloids other than gelatin are used alone or in 
combination of two or more, but they are usually used in combination with 
gelatin). To such hydrophilic organic colloid layers are added, in some 
cases, a polymer latex (e.g., polymethyl methacrylate latex, polyethyl 
acrylate latex, etc.) in order to improve the physical properties of the 
photographic layers and make the emulsion particles finer. 
As the hydrophilic organic colloid layer, there are illustrated silver 
halide photographic light-sensitive layers and non-light-sensitive 
photographic auxiliary layers (e.g., a protective layer, interlayer, 
filter layer, anti-irradiation layer, antihalation layer, backing layer, 
development stain-preventing layer, barrier layer, etc.).

The present invention will now be illustrated in more detail by reference 
to the following Examples. Unless otherwise indicated, all parts, 
percents, ratios, etc., are by weight. 
EXAMPLE 1 
A solution prepared by heating 19.1 g of cyan coupler, 
2-[.alpha.-(2,4-di-t-amylphenoxy)butanamido]-4,6-dichloro-5-methylphenol, 
19 g of Compound 10 of the present invention and 40 ml of ethyl acetate to 
70.degree. C. was added to 250 ml of an aqueous solution containing 25 g 
of gelatin and 1.5 g of sodium dodecylbenzenesulfonate, and stirred. Then, 
the mixture was passed 5 times, after pre-heating, through a colloid mill. 
As a result, the coupler was finely emulsified and dispersed together with 
the solvent. 
The emulsion dispersion was added to 1.0 kg of a photographic emulsion 
containing 54 g of silver bromoiodide emulsion and 60 g of gelatin and, 
after adding 30 ml of a 5% acetone solution of triethylenephosphamide as a 
hardener, the pH of the mixture was adjusted to 6.0, followed by coating 
on a cellulose triacetate film base in a dry thickness of 7.0.mu.. Thus, 
there was prepared Sample A. 
In the same manner as described above except using Compounds 1, 3 or 11 in 
place of Compound 10 in the same amount, there were prepared film Samples 
B, C and D. For the purpose of comparison, film Sample E was prepared in 
the same manner as above except using dibutyl phthalate (DBP) in place of 
Compound 10 in the same amount. 
These samples were subjected to stepwise exposure for sensitometry, then 
the following processings were carried out. 
______________________________________ 
Color Development Processing Step 
______________________________________ 
1. Color Development 
30.degree. C. 
4 min 
2. Bleach-Fixing " 2 min 
3. Washing with Water 
" 2 min 
4. Stabilizing Bath 
" 2 min 
______________________________________ 
Compositions of the respective processing solutions in the color 
development steps are as follows: 
______________________________________ 
Color Developer 
Sodium Metaborate 25 g 
Sodium Sulfite 2 g 
Hydroxylamine (sulfate) 2 g 
Potassium Bromide 0.5 g 
6-Nitrobenzimidazole (borate) 
0.02 g 
Sodium Hydroxide 4 g 
Benzyl Alcohol 15.8 ml 
Diethylene Glycol 20 ml 
4-(N-Ethyl-N-.beta.-methanesulfonamidoethyl)- 
8 g 
amino-2-methylaniline Sesquisulfate 
Water to make 1 l 
(pH: 10.2) 
Bleach-Fixing Solution 
Fe (II) Ethylenediaminetetraacetate 
45 g 
Ammonium Thiocyanate 10 g 
Sodium Sulfite 10 g 
Ammonium Thiosulfate (60 wt % aq. soln.) 
100 ml 
Sodium Ethylenediaminetetraacetate 
5 g 
Water to make 1 l 
(pH: 6.9) 
Stabilizing Bath 
Tartaric Acid 10 g 
Zinc Sulfate 10 g 
Sodium Metaborate 20 g 
Water to make 1 l 
______________________________________ 
Moist heat stability tests were conducted on the thus-developed film 
samples. The fastness of the samples after 1 week at 100.degree. C. and 
the fastness after 6 weeks at 60.degree. C. and 75% RH are indicated in 
Table 1 in terms of % reduced density based on the initial density. 
TABLE 1 
______________________________________ 
100.degree. C., 1 Week 
60.degree. C., 75% RH, 6 Weeks 
D.sub.0.5 
D.sub.1.5 
D.sub.0.5 
D.sub.1.5 
Sample 
Compound (%) (%) (%) (%) 
______________________________________ 
A 10 34 38 7 9 
B 1 41 42 12 16 
C 3 38 42 11 14 
D 11 35 40 8 11 
E DBP 60 65 19 21 
______________________________________ 
The greater the reduction in density, the poorer is the fastness. 
As is clear from Table 1, Sample E wherein the coupler was dispersed using 
DBP suffered serious fading of color images under humidity, whereas 
Samples A to D of the present invention suffered remarkably less color 
fading. 
EXAMPLE 2 
Sample F was prepared in the same manner as in Example 1 except for using 
9.5 g of Compound 10 and 9.5 g of DBP in place of 19 g of Compound 10, and 
a humidity test was conducted simultaneously with Sample E of Example 1 in 
the same manner as in Example 1 to obtain the results shown in Table 2 
below. 
TABLE 2 
______________________________________ 
100.degree. C., 1 Week 
60.degree. C., 75% RH, 6 Weeks 
D.sub.0.5 
D.sub.1.5 
D.sub.0.5 
D.sub.1.5 
Sample 
Compound (%) (%) (%) (%) 
______________________________________ 
F 10 + DBP 45 48 10 14 
E DBP 62 68 18 21 
______________________________________ 
The above results show that the epoxy compound of the present invention can 
remarkably improve resistance to moist heat fading even when used together 
with another high boiling organic solvent. 
EXAMPLE 3 
On a paper support laminated with polyethylene on both sides were coated 
the following first layer (lowermost layer) to the sixth layer (uppermost 
layer) to prepare a multilayer color light-sensitive material (Sample G). 
In the table "mg/m.sup.2 " represents the coated amount. 
______________________________________ 
6th layer Gelatin: 1,500 mg/m.sup.2 
(protective 
layer): 
Silver chlorobromide 
5th layer (red- 
emulsion (AgBr: 
50 mol %; 
sensitive layer): 
silver: 300 mg/m.sup.2) 
Gelatin: 1,500 mg/m.sup.2 
Cyan coupler (*1): 
500 mg/m.sup.2 
Coupler solvent (*2): 
250 mg/m.sup.2 
4th layer (UV ray- 
Gelatin: 1,200 mg/m.sup.2 
absorbing layer): 
UV ray-absorbing 1,000 mg/m.sup.2 
agent (*3): 
Solvent for UV absorbing 
250 mg/m.sup.2 
agent (*2): 
Silver chlorobromide 
3rd layer (green- 
emulsion (AgBr: 
50 mol %; 
sensitive layer): 
Ag: 450 mg/m.sup.2) 
Gelatin: 1,500 mg/m.sup.2 
Magenta coupler (*4): 
400 mg/m.sup.2 
Coupler solvent (*5): 
200 mg/m.sup.2 
2nd layer: Gelatin: 1,000 mg/m.sup.2 
Silver bromochloride 
1st layer (blue- 
emulsion (AgBr: 
80 mol %; 
sensitive layer): 
Ag: 450 mg/m.sup.2) 
Gelatin: 1,500 mg/m.sup.2 
Yellow coupler (*6): 
500 mg/m.sup.2 
Coupler solvent (*7): 
500 mg/m.sup.2 
Support: Polyethylene laminated 
paper 
*1 Cyan coupler: 
2-[.alpha.-(2,4-di-t-amylphenoxy) 
butanamido]-4, 
6-dichloro-5-methylphenol 
*2 Coupler solvent: 
di-n-butyl phthalate 
*3 UV ray-absorbing 
agent: 
2-(2-hydroxy-3-sec-butyl-5- 
t-butyl- 
phenyl)benzotriazole 
*4 Magenta coupler: 
1-(2,4,6-trichlorophenyl)-3- 
[2-chloro-5-tetradecana- 
mido]anilino-2-pyrazolin- 
5-one 
*5 Coupler solvent: 
o-cresyl phosphate 
*6 Yellow coupler: 
.alpha.-pivaloyl-.alpha.-[2,4-dioxo-5, 
5'-dimethyl- 
oxazolidin-3-yl]- 
2-chloro-5-[.alpha.-2,4-di-t- 
.alpha.-2,4-di-t- 
amylphenoxy)butanamido] 
acetanilide o-dioctylbutyl 
*7 Coupler solvent: 
phosphate 
______________________________________ 
Sample H was prepared wherein the coupler solvent in the 5th layer of 
above-described Sample G was replaced by Compound 10 of the present 
invention. In Sample H, too, the ratio of the weight of cyan coupler to 
the coupler solvent was adjusted to 2:1 which was the same as with 
comparative Sample G. 
Each sample was exposed for 1/2 second to blue light, green light and red 
light through a continuous wedge, then subjected to the following 
processings: 
______________________________________ 
Temperature 
Step Time (.degree.C.) 
______________________________________ 
1. Color Development 
3 min 30 sec 
33 
2. Bleach-Fixing 1 min 30 sec 
33 
3. Washing with Water 
2 min 33 
4. Drying 
Composition of the Developer 
Benzyl Alcohol 15 ml 
Sodium Sulfite 5 g 
Potassium Bromide 0.5 g 
Hydroxylamine Sulfate 2.0 g 
Sodium Carbonate 30.0 g 
Sodium Nitrilotriacetate 2.0 g 
4-Amino-3-methyl-N-(.beta.-methane- 
5.0 g 
sulfonamido)-ethylaniline 
Water to make 1,000 ml 
(pH: 10.1) 
Composition of 
Bleach-Fixing Solution 
Ammonium Thiosulfate 105 g 
Sodium Sulfite 2 g 
EDTA Disodium Salt 40 g 
Sodium Carbonate (H.sub.2 O) 5 g 
Water to make 1,000 ml 
(pH: 7.0) 
______________________________________ 
When the resulting samples were left for 1 week in a dark room at 
100.degree. C., and when left for 6 weeks in a dark room at 60.degree. C. 
and 75% RH, reductions in cyan color image density based on the initial 
density thereof were as tabulated in Table 3. (The greater the values, the 
poorer is the fastness.) 
TABLE 3 
______________________________________ 
100.degree. C., 1 Week 
60.degree. C., 75% RH, 6 Weeks 
D.sub.0.5 
D.sub.1.5 
D.sub.0.5 
D.sub.1.5 
Sample 
Compound (%) (%) (%) (%) 
______________________________________ 
G* DBP 61 65 19 22 
H** 10 40 42 7 8 
______________________________________ 
*comparative example 
**present invention 
It is seen from the above results that, when used in a stratum structure 
system, the epoxy compound of the present invention provides good 
photographic properties and enables one to form color images with good 
moist heat stability. Similar results were obtained when Compound 1, 3 or 
11 was used in place of Compound 10. 
EXAMPLE 4 
When the same tests as described in Example 1 were conducted using Cyan 
Coupler 2 
(2-[.alpha.-(2,4-di-t-amylphenoxy)-acetamido]-4,6-dichloro-5-methylphenol) 
and Cyan Coupler 3 (2-tetradecanamido-4-chloro-5-methylphenol), the 
following results were obtained with respect to density reduction ratio. 
TABLE 4 
______________________________________ 
Density Reduction after 
1 Week at 100.degree. C. 
D.sub.0.5 D.sub.1.5 
Sample Compounds Used 
(%) (%) 
______________________________________ 
I* Coupler 2, 
Compound 10 39 41 
J** Coupler 2, 
DBP 68 69 
K* Coupler 3, 
Compound 10 34 31 
L** Coupler 3, 
DBP 40 38 
______________________________________ 
*present invention 
**comparative example 
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.