JPS62131259A - Silver halide photographic sensitive material - Google Patents

Abstract

PURPOSE:To obtain the silver halide color photosensitive material having a reduced yellow stain which is formed by light, heat and humidity by using jointly an epoxy compd. with a 3-anilino type 5-pyrazolone coupler having a specific structure. CONSTITUTION:The magenta color image forming coupler shown by formula I and the epoxy compd. which is hard to dissolve to water and is shown by formula II are incorporated to the silver halide color photographic sensitive material. In formula I, Ar is phenyl having one halogen atom, etc., Y is an alkoxy group, R1 is an acylamino group not contg. a hydroxyphenyl group, (m) is an integer of 1-4, Z is hydrogen atom or a group capable of cleaving by coupling with an oxidative product of the aromatic primary amine. In formula II, R2-R5 are each hydrogen atom or an aliphatic group, etc., R2-R5 are not all hydrogen at the same time, the total carbon numbers are 8-60. Thus, the titled material having a high durability against light, heat or humidity, and capable of effectively depressing the generation of the yellow stain without using the stabilizer of the color image is obtd.

Description

Detailed Description of the Invention (Field of Industrial Application) The present invention relates to a silver halide color photographic light-sensitive material containing a 3-anili/-5-pyrazolone type magenta coupler and an epoxy compound that is sparingly soluble in water. More specifically, the present invention relates to a silver halide color photographic light-sensitive material in which yellow stain generated when exposed to light, heat, and humidity is reduced.

(Prior art) When a silver halide color photographic light-sensitive material is color-developed, an oxidized aromatic primary amine color developing agent and a coupler react with each other to produce indophenol, indoaniline, indamine, azomethine, phenoxyphenol, etc. It is well known that sazine, phenazine and similar pigments are produced to form color images. Among these, 5-pyrazolone, cyanoacetophenone, intasolone, pyrazolobenzimidazole, and pyrazolotriazole couplers are known for forming magenta images.

Among these, dyes formed from 5-pyrazolone couplers have excellent fastness to heat and light, but the couplers themselves are susceptible to heat, light, and humidity and are easily decomposed. This tendency was known to be large in couplers.

Various studies have been conducted to reduce the yellow stain that occurs when exposed to heat, light, and humidity.

It is known from US Pat. No. 4,239,851 to introduce epoxy compounds into photographic systems. However, although the US patent specification describes in detail its effectiveness for cyan color images, it does not mention any application examples for magenta couplers.
An example of a terminal epoxy compound is reported in No. 0,657, and it is stated that when used in combination with a magenta coupler, it is effective in reducing the yellow stain caused by magenta coupler due to heat, light, and humidity.

(Problems to be Solved by the Invention) However, according to the examples described in the above-mentioned US patent specification, the silver halide photographic light-sensitive material requires the use of an anilino-type magenta coupler together with a color image stabilizer.
Furthermore, in order to stabilize the anilino-type magenta coupler without using a color image stabilizer in combination, it is necessary to contain a color image stabilizing functional group in place of the color image stabilizer in the molecule of the anilino-type magenta coupler.

Therefore there is no need for color image stabilizers, light or heat.

Contains an anilino-type magenta coupler that does not easily produce yellow stain even when exposed to humidity. The development of new silver halide color photographic materials is desired.

(First Step to Solve the Problem) The present inventors have conducted intensive research to develop a silver halide color photographic light-sensitive material that uses pyrazolone couplers and reduces yellow stain generated by light, heat, and humidity. As a result of repeated research, it was discovered that the object could be achieved by using an epoxy compound in combination with a 3-anilino type 5-pyrazolone coupler having a specific structure, and based on this knowledge, the present invention was accomplished.

That is, the present invention provides a silver halide color photographic photosensitive material containing a magenta image-forming coupler represented by the following general formula [I] and a sparingly water-soluble epoxy compound represented by the following general formula (11). It provides materials.

General formula [I] A" (However, Ar represents a phenyl group having at least one halogen atom, alkyl group, alkoxy group, cyan group, or alkoxycarbonyl group, Y represents an alkoxy group or a halogen atom, R1 represents an acylamino group, sulfonamido group, alkoxycarbonyl group, carbamoyl group, sulfamoyl group, isido group, halogen atom, alkoxy group, alkyl group, or alkylthio group that does not have a hydroxyphenyl group, and 1m is 1 to 4
and Z represents a hydrogen atom or a group that leaves after coupling with an oxidation product of an aromatic primary amine. General formula (II) R5 each represents a hydrogen atom, an aliphatic group, an aliphatic oxycarbonyl group, an aromatic oxycarbonyl group, or a carbamoyl group, provided that R, R,, R4 and R are all hydrogen atoms at the same time. There is no such thing, and the total number of carbons is 8
~60. ).

Ryu and R3 or R4 and R5, each 5 to 7
The compounds of general formula [I] and general formula (11) will be explained in more detail.

In the general formula (I), Ar is at least one halogen atom (e.g., chlorine atom, fluorine atom, bromine atom, etc.), an alkyl group (e.g., methyl, (, ethyl, dodecyl, ':4), Alkoxy group (e.g. methoxy group, ethoxy 7, ti, octyloxy group, etc.), cyano group or alkoxycarbonyl) & (e.g. me)+
represents a phenyl group having a dicarbonyl group, ethoxycarbonyl group, dodecyloxycarbonyl group, etc.), and Y
is an alkoxy group (e.g., methoxy group, butyloxy group, dodecyloxy group, etc.) or a halogen atom (e.g., fluorine atom, chlorine atom, bromine atom).

), R represents an acylamino group having no hydroxyphenyl group (e.g., acetamido group, pivaloylamino group, tetradecanamide group, α-(2,4-di-tert-amylphenoxy)butyramide group, etc.),
Sulfonamide groups (e.g. methanesulfonamide group, octane sulfonamide group, 4-dodecyloxybenzenesulfonamide group, 2-butoxy-5-t-octylbenzenesulfonamide group, etc.), alkoxycarbonyl groups (e.g. ethoxy carbonyl group.

Tetradecyloxycarbonyl group, 2-(2,4-di-tert-amylphenoxy)ethoxycarbonyl group 1
), carbamoyl group (e.g., N-methylcalyl group, N-(2-dodecyloxyethyl)cal/<moyl group, N-(3-(2,4-di-tert-amylphenoxy)propyl)carbamoyl group, N -methyl-N-octylcarbamoyl group, etc.), sulfamoyl group (e.g., N-ethylsulfamoyl group, N-F
T'silsulfamoyl group, N,N-didodecylsulfamoyl group, N.

N-diethylaminosulfamoyl group, etc.), imide group (e.g., N-succinimide group, N-(3-octadecenylsuccinimide group, l-dodecyl-3-hydantoyl group.W), halogen atom (e.g., chlorine atom, bromine atom, etc.), alkoxy groups (e.g. methoxy group, dodecyloxino, etc.), alkyl groups (e.g. methyl group, t-butyl group, t-octyl group, pentadecyl group, etc.).

etc.), or an alkylthio group (e.g., ethylthio group,
2 represents a hydrogen atom or a halogen atom (e.g., chlorine atom, bromine atom, iodine atom, etc.), a carboxyl group, or a group linked with an oxygen atom (e.g., an acetoxy group); , propanoyloxy group, benzoyloxy group, 2,4-dichlorobenzoyloxy group, ethoxyoxaloyloxy group, pyruvinyloxygen, cinnamoyloxy group, phenoxy, '!.4-cya/phenoxyl group.

4-methanesulfonamidophenoxy group, 4-methanesulfonylphenoxy group, α-naphthoxinov, 3-pentadecylphenoxy group, benzyloxycarbonyloxy group, ethoxy group, 2-cyanoethoxy group, benzyloxy group, 2-phenethyloxy group, 2-phenoxyethoxy group, 5-phenyltetrazolyloxy group, 2-benzothiazolyloxy group, etc.), groups linked through nitrogen atoms (
For example, benzenesulfonamide group, N-ethyltoluenesulfonamide group, pebtafluorobutanamide group,
2,3,4,5.6-pentafluorobenzamide group,
Octanesulfonamide group, P-cyanophenyl ureate group, N,N-diethylsulfamoylamino group, l-
Piperidyl group, 5,5-dimethyl-2,4-dioxo-
3-oxasolidinyl group, l-benzyl-ethoxy-3
-hydantoinyl/, %, 2N-1,1-dioxo-3
(2H)-xo1,2-benzisothiazolyl group,
2-oxo-1,2-dihydro-1-pyridinyl group, imidazolyl group, pyrazolyl group, 3゜5-diethyl-1,
2,4-) riazol-1-yl, 5- or 6-promobenztriazol-1-yl, 5-methyl-1,
2,3,4-) lyazol-1-yl group, benzimidazolyl group, 3-benzyl-1-hydantoinyl 1.1-
benzyl-5-hexadecyloxy-3-hydantoynyl group, 5-methyl-1-tetrazolyl group, etc.), arylazo group (e.g., 4-methoxyphenylazo group, 4
-pivaloylaminophenylazo group, 2-naphthylazo group, 3-methyl-4-hydroxyphenylazo group, etc.)
, a group linked by a sulfur atom (e.g., phenylthio group,
2-carboxyphenylthio group, 2-methoxy-5-t
-Octylphenylthio group, 4-methanesulfonylphenylthio group, 4-octanesulfonamidophenylthio group, 2-butoxyphenylthiono A, ? -(2-hexanesulfonylethyl)-5-tert-octylphenylthio group, benzylthionon, ? -cyanoethylthio group, 1-ethoxycarbonyltridecylthio group, 5-phenyl-2゜3.4.5-tetrazolylthio group, 2-penzothiazurylthio group, 2-dodecylthio-5-thiophenylthio group, 2-phenyl-3-doa'sil-1,2,
4-) represents a riazolyl-5-thio group (1, etc.).

In general formula (11), R2, R3, R4 and R5
is a hydrogen atom, an aliphatic group, an aliphatic oxycarbonyl group (e.g., dodecyloxycarbonyl group, allyloxycarbonyl group, etc.), an aromatic oxycarbonyl group (e.g., phenoxycarbonyl group, etc.), or a carbamoyl group (e.g., tetradecylcarbamoyl group), respectively. Moylno A, etc.), but R7, R8, R9 and Rlo are not all hydrogen atoms at the same time,
The total number of carbon atoms is 8-60. These groups may have a substituent.

In general formula (m), R7 and R8 are or R and R9
may form a 5- to 7-membered ring.

In the general formula [I], the substituent for A is particularly preferably a halogen atom, Y is particularly preferably a chlorine atom, and R1 is particularly preferably an acylamino group or imido group having no hydroxyphenyl group. Z is preferably a group linked through a hydrogen atom or a sulfur atom, and particularly preferably a hydrogen atom.

In general formula (II), R, , R3, R4. R5
It is preferable that at least one of them is hydrogen, and 2
More preferably, it is hydrogen.

In general formula (II), R2'R3'R4
' At least one of R5 is substituted with an ester group, an amide group, or an aryl or alkyl ether group.
4 7, 1. J-11 tr-4
4, 1 = 1-4t h-L
1. %3- represented by general formula [I] according to the present invention
7 Nilino 5-pyrasolone type magenta coupler is disclosed in U.S. Pat. Nos. 3,684,514 and 3,935.

It can be synthesized by the method described in No. 015, No. 4,351,897, etc., and examples of compounds are shown below, but the compound is not limited thereto.

/′ C.L. α rJ.

t (+-8) CL (+-10) l Ct The compound of general formula (II) according to the present invention is disclosed in U.S. Pat.
．． It can be synthesized by the method described in No. 239,851 and No. 4,540,654, and examples of the compound are shown below, but the compound is not limited thereto.

(It-1) (n-2) (It-3) (■-4) (n-5) 2H5 2H5 (It-6) (n-7) (■-8) (It-9) (It- 10) (+1-11) (II-12) (n-13) (II-14) (U-15) (Il-16) (n-17) ([-tS) (It-19) 74,: The photographic emulsion layer of the Su゛Product゜1 light-sensitive material used in the invention contains silver bromide, silver iodobromide, silver iodo-11 bromide, silver m-bromide and 31! Any silver halide may be used. Preferred silver halides for direct viewing materials such as colorants are silver chloroiodobromide and silver iodochloride containing 7 mol% or less of silver iodide. or silver iodobromide or chlorobromide. Preferred for photographic materials is silver iodobromide containing from about 2 mol % to about 25 mol % silver iodide.

Silver halide grains in photographic emulsions are so-called ray 1 grains, which have regular crystal structures such as cubes, octahedrons, and tetradecahedrons.
It may be a particle with an irregular crystal shape such as a spherical shape, a crystal defect such as a twin plane, or a composite shape thereof.

The grain size of the silver halide may be fine grains of about 0.1 micron or less, large grains with a projected area diameter of about 10 microns, monodisperse emulsion with a narrow distribution, or polydisperse emulsion with a wide distribution. The /% silver lodenide photographic emulsion that can be used in the invention can be prepared by a known method, for example, Research Disclosure (RD), No. 1764.
3 (December 1978), 22-23L” 1. Emulsion preparation and
18716 (1979)
(November 2013), 648.

The silver halide α emulsion used in the present invention may be a mixture of separately formed silver halide H emulsions.

The emulsion consists of the above-mentioned regular grains.
It can be obtained by controlling IlA8 and l11-( during particle formation.
pl+ic 5science and Engineering
ring) No. 68, pp. 159-165 (1962): Journal of 7t Graphic Science (Jo
urnal ofPl+oLoFirapbic 5
science), vol. 12, pp. 242-251 (19
04), U.S. Patent No. 3,655,394 and Fukoku Patent No. 1,413,748.

Monodisperse IL agents include silver halide grains with an average grain diameter greater than about 0.1 micron, at least about 95% by weight of which is within ±40% of the average grain diameter. -L cutting is typical. Average particle diameter is approximately 0.25
-2 microns and having at least about 95% by weight or at least about 95% by number of silver halide grains within the range of average grain diameter ±20% can be used in the present invention. A method for producing such an emulsion is described in U.S. Pat. Nos. 3 and 5.
No. 74,628, No. 3,655.394 and British Patent No. tpJ1,413.748.

Tabular grains having aspect ratios of about 5 or more can also be used in the present invention. Tabular grains are described in CuLo [, Photographic Science and Engineering]
e and Engineering)+tlIJ
14, pp. 248-257 (1970); U.S. Patent Nos. 4,434,226, 4,414,310, 4,433.048, ? , 439,520 and British Patent No. 2,112,157, etc., 1sIl can be easily produced. When tabular grains are used, improvement of color sensitization efficiency by sensitizing dye,
Advantages and disadvantages, such as improved graininess and increased sharpness, are detailed in US Pat. No. 4,434,226, cited above.

These emulsion grains may have a uniform crystal structure, or may have a halogen composition with different internal and external components, and may have a layered structure.
No. 6, U.S. Patent No. 3,505.068, Im4,44
No. 4,877 Oyohi! It is disclosed in U.S. No. 58-248409 and the like. Further, silver halides having different compositions may be bonded by epitaxial bonding, or compounds other than silver halide such as silver oxide or lead oxide may be bonded.

Even if a mixture of grains of various crystal forms is used, the emulsion of the present invention is usually one that has been subjected to physical ripening, chemical ripening, and spectral sensitization. The additives used in this process are listed in Research Disk a-no+-No. 17.
643 and No. 18716, and the relevant parts are summarized in the table below.

Known photographic additives that can be used in the present invention are also listed in the above two Research Disclosures, and their locations are shown in the table below.

7・″ /′ , /7′ x′ /′ , / 1 Japanese sensitizer 2:1 !T Page 648 right column 2 Sensitivity 1. 1 reduction Same as above 3 Spectral sensitizer, 2:1 = page 24 648T;X Right column - Super sensitizer Page 649 Right column 4 Brightener
24i 5 Anti-wrinkle removal 24-25i Page 649 Right column and stabilizer 6 Light absorber, 7 Pages 25-26 649 Right column - Ilter dye 650 Left column Ultraviolet absorption remover 7 Stain inhibitor Page 25 Column Ij Page 650 Left to right column 8
Dye image stabilizer page 25 9 Hardener page 26 page 651 left column 10 binder 26T; c Same as above X1 plasticizer, lubricant page 27 650 right column 12 coating aid, table
Pages 26-27 Same as above Surface activator 13 Statink prevention Page 27 Same as above Stop scraping Various color couplers can be used in the present invention, specific examples of which can be found in the above-mentioned Research Dischrono +
(l?D) No. 17643, ■-C-G, the zero dye-forming power puller provides the three primary colors (i.e., yellow, agenta and cyan) in subtractive color development through color development. Specific examples of 4-equivalent or 2-equivalent couplers in which the coupler is mold-resistant and diffusion-resistant are mentioned above.
In addition to the couplers described in the patents D17643, ■-C and item 0, the following can be preferably used in the present invention.

A representative example of the yellow coupler that can be used in the present invention is a hydrophobic acylacetamide coupler having a Balan F group. A specific example is U.S. Pat.
No. 407,210, US Pat. No. 2,875.057, and US Pat. No. 194, No. 3.447,928
No. 3,933,501 and No. 4,022,
620, etc., or Japanese Patent Publication No. 5B-10739, U.S. Patent t.
ItJ4,401,752, ItJ4,326.024
No., RD18053 (April 1979), British Patent No. 1
．． No. 425,020, West German Application Publication rW1 No. 2,219.
917, Pt52.2G1.361, Pt2.3
Typical examples include the nitrogen atom separation type yellow couplers described in Japanese Patent No. 29,587 and No. 2,433.812. The a-pivaloyl acetanilide coupler has excellent color fastness, particularly light fastness, while the a-benzoyl 7cetanilide coupler provides a high color density.

Cyan couplers that can be used in the present invention include hydrophobic and diffusion-resistant 7-toll and 7-enol couplers, such as the 7-enol couplers described in U.S. Pat. No. 2,474,293.
Tall couplers, preferably U.S. Pat. No. 4,052,
No. 212, No. 4,146.396, No. 4,228
Typical examples include the ex-atom-eliminating type two-equivalent 7 toll P couplers described in , No. 233 and No. 4,296,200. Further, specific examples of 7-el couplers are disclosed in U.S. Patent Nos. 2,369,929 and 2,8.
No. 01.171, No. 2,772,162, No. 2.
No. 895,826, etc.

Couplers that can form cyan dyes that are stable against humidity and temperature are preferably used in the present invention, and typical examples thereof include the 7 ether branch described in U.S. Pat. No. 3,772,002. 7-ethyl cyan coupler having a dimethyl or higher alkyl group at the meta-position, U.S. Patent No. 2,7
No. 72,162, No. 3,758,308, PIS
No. 4,126.396, No. 4,334,011, No. 4,327.173, West German Patent Publication No. 3,329,
No. 729 and European ffl patent no. 121.305? ytGrL3hf2.5-noacylami/substituted 7e7-
couplers and U.S. Pat. No. 3,446,622;
PIS No. 4,333.999, PIS No. 4,451,55
9 and fpJ4.427.767, etc., and 7-er/-el couplers having a mi/group at the 2-position.

Patent application No. 59-93605. The cyan couplers described in 59-204277 and 59-268135 in which the 5-position of the 7-tole is substituted with a sulfonamide group, amide group, etc. also have excellent fastness of colored images, and are preferably used in the present invention. can.

In order to correct unnecessary absorption of chromophores, it is preferable to use a colored coupler in color photosensitive materials for photographing to perform masking, as disclosed in U.S. Pat. Yellow colored magenta coupler described in US Patent tPJ4,004.92
No. 9, No. 4,138.258 and British Patent No. 1.
Typical examples include the magenta-colored cyan coupler described in No. 146.368. Other colored couplers are described in RD 17643.1-6 above.

Couplers that release photographically useful residues upon coupling can also be preferably used in the present invention.
The patented couplers described in Section 3.-F are useful.

The color photographic material according to the present invention includes the above-mentioned RD, N
o, 17643 28-29g 1 hour, No. 187
16-651 left column to right column can be used for development processing.

The color photographic material of the present invention is usually subjected to a water washing treatment or a stabilization treatment after development, bleach-fixing or fixing treatment.

In the washing process, two or more tanks are generally flushed with water to save water. A representative example of the stabilization treatment is a multistage countercurrent stabilization treatment as described in JP-A-57-8543 instead of the water washing step. In the case of this process, 2 to 9
A tank countercurrent column is required. Various compounds are added to this stabilizing bath for the purpose of stabilizing images. For example, membrane LIH
Various buffers (for example, pH 3 to 8)
For example, borate, metaborate, borax, phosphate,
Typical examples include carbonates, potassium hydroxide, sodium hydroxide, aqueous ammonia/carboxylic acids, nocarboxylic acids, polycarboxylic acids, etc.) and formalin. Other water softening nI as required
! <gw phosphoric acid, aminopolycarboxylic acid, organic phosphoric acid,
(amino/polyphosphonic acid, phospho/carboxylic acid, etc.), fungicides (benzisothiazolinone, isothiazolone, 4-
Various additives such as surfactants, optical brighteners, hardeners, etc.), surfactants, optical brighteners, hardeners, etc. may be used, and target compounds of the same or +A class may be used. You may use two or more types together.

In addition, the membrane after treatment, ammonium chloride as an H adjuster,
It is preferable to add various ammonium salts such as ammonium nitrate, ammonium sulfate, ammonium phosphate, heptammonium sulfite, and ammonium periosulfate.

The present invention can be applied to various color photosensitive materials. Typical examples of the present invention include color box film for general use or movies, color reversal film for slides or television, color vapor, color box film, and color reversal paper. Research Disclosure 17123 (197
It can also be applied to black-and-white light-sensitive materials using a mixture of three color couplers as described in J.

(Effects of the Invention) The silver halide photographic light-sensitive material of the present invention has the advantage that it has high fastness to light, heat, and humidity without using a one-color image stabilizer, and can effectively reduce the occurrence of yellow stain. It has a great effect. Further, by taking advantage of this property, silver halide photographic materials can be made thinner.

(Example) Next, the present invention will be explained in more detail based on examples.

Example 1 After coating a coating solution having the composition shown in Table 1 on a polyethylene (PET) support, gelatin (1500
mg/rn') was prepared (sample $4A-
1-A-13).

12.3 g of magenta (I-1) shown in Table 1 was heated and dissolved in 11.3 g of epoxy compound (IT-9) and 20 m of ethyl sulfate, and 10 g of gelatin and 1.0 g of sodium dodecylbenzenesulfonate were dissolved. It was added to 100 g of an aqueous solution containing the above ingredients and emulsified and dispersed. The entire amount of this emulsion was added to 235 g of a photographic emulsion containing 25 g of silver chlorobromide, and 31 coats of coating solution 4j were applied. 2,4-dichloro-6-hydroxys-triazine-sodium 1'11 was used as a hardening agent and coated on the support, and gelatin ctooomg was further added as a protective layer.
/m') was coated and dried to obtain a test sample 1-1. Other samples were prepared in a similar manner.

These samples 1 were exposed to red light through a continuous wedge and then developed using the following processing steps.

2-', C, /'/' Pressing process 1 Temperature Time Developer solution
33°C 3 minutes 30 seconds Internal fixer 33°
C1 minute 30 seconds water washing 28-35°C 3 minutes The formulation of the treatment solution used is as follows.

Benzyl alcohol 15m diethylene glycol 8m ethylenediaminetetravinegar disodium JII 5g Sodium sulfite 2g hydroxylcyamine sulfate 3g 4-Amino-N-ethyl-N- (β-methanesulfonamidoethyl)-m-toluidine φ2/ 3 Add sulfate/monohydrate 5g water and adjust the pH to 1000+nQ 10,20 Ethylenediaminetetraacetic acid ψ Disodium salt 2g ethylenecyaminetetraacetic acid #ferric kll 40g Sodium sulfite 5g 1,000 neoammonium sulfate 70g Add water 1
000m pH 6, 80km adjustment After each test sample 4 at 100℃ 21! Interval preservation and 7
The sample was stored at 0° C. and 70% RH for 10 days and irradiated with light for 8 days using a xenon fading tester (100,000 lux) to perform a discoloration test. Reconnaissance color stain density (DB) generated in unexposed areas
) was measured using a Macbeth RD-514 model C degree meter.

The results are shown in Table II.

Comparative coupler (1) From the results in Table II, it can be seen that in the silver halide photographic material according to the combination 1 of the present invention, the increase in yellow density due to heat, light, and humidity is suppressed to 1 1 J 1 pt. In other words, epoxy compounds are generally effective in increasing the yellow density of 3-anilino-5-viraturon couplers, but
Among them, it is found that the coupler of the present invention having no hydroxyphenyl group is particularly effective. Furthermore, it can be seen that among the epoxy compounds, terminal epoxy compounds have a greater effect of suppressing yellow density.

Example 2 A color photographic material was prepared by coating the first layer (lowest layer) to the seventh layer (top layer) on double-sided polyethylene laminated paper as described in Tables M and II.

(Sample B-E) The coating liquid for the first layer was prepared as follows. That is, 100 g of the yellow coupler shown in Table M was mixed with 100 g of dibutyl phthalate (DBP), and this solution was emulsified and dispersed in 800 g of a 10% aqueous gelatin solution containing 80 ml of a 1% aqueous solution of sodium dodecylbenzenesulfonate.
Next, the total value of this emulsified dispersion was converted into a blue-sensitive silver chlorobromide emulsion (Br8
0%) (contains 66.7 g of Ag) to prepare a coating solution. Other layers are also QIn by the same method.
A liquid was prepared. As a hardening agent for each layer, 2°4-dichloro-6-hydroxy-s-triazine sodium salt was used.

The following spectral sensitizers were used for each emulsion.

S-sensitive emulsion layer, 3.3'-G (γ-sulfopropyl)
- Selenacyanine sodium salt (2 xio' mol per 1 mol of silver halide) Green-sensitive emulsion layer; Con sodium 11! (Silver halide 1 Mo A-red sensitive emulsion layer, 3.3'-di(γ-sulfopropyl)
-9-Methyl-thiacycarpo cyanin sodium kit (2.5 x 10''4 mol per mol of silver halide) The following dye was used as the anti-irradiation 11 dye in each emulsion layer.

Green-sensitive emulsion layer Red-sensitive emulsion layer SOJ S05 In the table, TNP is trinonyl phosphate, DBP is dibutyl phthalate, and TOP is tris (2-ethylhexyl).
Phosphe-1., TCP represents trinonyl phosphate, and the chemical structures of the compounds (tree a) to (zero g) are as follows.

(*a) Cyan coupler (wood a') Cyan coupler (wood b) Anti-fading agent (*C) Anti-fading agent (umbrella d) Yellow coupler (umbrella e) Anti-fading agent book f Ultraviolet absorber (1:5: *g Ultraviolet absorber C4M9 (t) (1:3:3 mixture) Development was carried out in the same manner as in Example 1.

After the development process, each sample was stored at 100° C. for 2 hours, and a discoloration/fading test was conducted. After the test, each sample was adjusted to a pre-test concentration of 1.0.
C degree was measured using a Macbeth RD-514 type densitometer at the location. The results are shown in Table-■.

Table V The results in Table V show that the combination of the coupler of the present invention and the epoxy compound is effective in reducing the color stain density and has excellent fastness under light irradiation.

Patent applicant: Fuji Photo Film Co., Ltd. 7-, -m-
1,.

Claims (1)

[Scope of Claims] A silver halide color characterized by containing a magenta image-forming coupler represented by the following general formula [I] and a sparingly water-soluble epoxy compound represented by the following general formula [II] Photographic material. General formula [I] ▲ Numerical formulas, chemical formulas, tables, etc. group or a halogen atom, R_1 is an acylamino group that does not have a hydroxyphenyl group, a sulfonamide group, an alkoxycarbonyl group, a carbamoyl group, a sulfamoyl group, an imide group, a halogen atom, an alkoxy group,
represents an alkyl group or an alkylthio group, m is 1 to
represents an integer of 4, and Z represents a hydrogen atom or a group that leaves after coupling with an oxidation product of an aromatic primary amine. ) General formula [II] ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (However, R_2, R_3, R_4 and R_5 are hydrogen atoms, aliphatic groups, aliphatic oxycarbonyl groups,
represents an aromatic oxycarbonyl group or a carbamoyl group (however, R_2, R_3, R_4 and R_5 are not all hydrogen atoms at the same time, and the total number of carbon atoms is 8 to 60), R_2 and R_3 or R_4
and R_5 may each form a 5- to 7-membered ring. )