JPS60194452A - Silver halide color photosensitive material - Google Patents

Abstract

PURPOSE:To prevent fog, to reduce an amt. of silver halide, etc., to be used in a photographic emulsion layer, and to enhance resistances to light, heat, etc., by using a specified coupler made of a pyrazolone deriv. as a magenta coupler. CONSTITUTION:An intended silver halide photosensitive material can be obtained by incorporating, in a photographic constituent layer formed on a support, a magenta coupler, such as formulae II and III, represented by general formula I in which Ar is aryl; R1 is alkyl or cycloalkyl; R2 is alkyl, aryl, or the like; R3 is halogen, alkyl, or the like; and (m) is 0-4. Said compd. can be synthesized by dibrominating the 4-position of the pyrazolone coupler and reacting it with mercaptan in an amt. of about 3mol per mol of the pyrazolone or the like method. Said coupler is used usually in an amt. of 0.007-0.7mol per mol of silver halide.

Description

DETAILED DESCRIPTION OF THE INVENTION (1) Background of the Invention Technical Field The present invention relates to a silver halide color photographic light-sensitive material containing a novel magenta dye-forming coupler.

Prior art and its problems As is well known, in subtractive color photography, an aromatic primary amine color developing agent produces oxidation products of the color developing agent by reducing exposed silver halide grains. A dye image is formed by oxidative coupling of yellow, cyan, and magenta dye forming couplers in a silver halide emulsion. In these cases, as a yellow coupler to form a yellow dye, a compound having an open-chain active methylene group is generally used, and as a magenta coupler to form a magenta dye, a pyrazolone type, pyrazolotriazole type, or pyrazolone type is used. Compounds such as nobenzimidazole and indacylon are used, and phenol and naphthol compounds are used as cyan couplers to form cyan color patches.

Each coupler is dissolved in a substantially water-insoluble high-boiling organic solvent.
Alternatively, it can be dissolved in a silver halide emulsion using an auxiliary solvent if necessary, or it can be dissolved in an alkaline aqueous solution and added to a silver halide emulsion. The former is called an oil droplet dispersion method, and the latter is called an alkaline dispersion method, and the former is generally considered to be superior to the latter in terms of light resistance, heat resistance, temperature resistance, color sharpness, etc. ing.

The basic properties required of each coupler are not only to form a dye, but also to have high solubility in high-boiling organic solvents or alkalis, as well as dispersibility and stability in silver halide photographic emulsions. The good thing is that the dye formed by it has fastness to light, heat, moisture, etc., has good spectral absorption characteristics, good transparency, and high color density. It is desired that the images produced have various characteristics such as excellent sharpness and graininess.

However, to the best of the knowledge of the present inventors, no conventionally known magenta coupler has yet been found that satisfies all of the above-mentioned required properties.

Various pyrazolone derivatives are known as magenta couplers, but these couplers have low coloring efficiency, and in the case of so-called four-equivalent couplers in which the coupling active site is unsubstituted, the ratio of coupler used for dye formation is about half. However, the remainder had the disadvantage of low color development efficiency, meaning that it was not useful for pigment formation.

As a method for improving this coloring efficiency, a so-called two-equivalent magenta coupler is known in which a substituent (leaving group) capable of splitting off during color development is introduced into the active position of a pyrazolone derivative. As these two-equivalent magenta couplers, for example, couplers having an acyloxy group as a leaving group are disclosed in U.S. Pat. No. 3,311,476, and couplers having an aryloxy group are disclosed in U.S. Pat. No. 3,419,391.
In U.S. Pat.
214.437 and 3. '253,924, 2
- Couplers having triazolyl groups are disclosed in U.S. Patent Nos. 3 and 6.
No. 17,291 and couplers having acylthio or thioacylthio groups are described in U.S. Pat. No. 4.032.346, respectively. However, when these two-equivalent magenta couplers are used, significant color fogging may occur, coupling activity may be low, or the couplers may be chemically unstable and turn into substances that cannot develop color over time. However, these methods have been associated with some disadvantages, such as a high level of difficulty in synthesis.

In addition, as disclosed in U.S. Pat. compounds were also known. However, many of these known thio-substituted pyrazolone compounds are so-called development inhibitor-releasing couplers (DIR).
The mercaptan produced as a result of the coupling reaction interacts with silver halide and has the function of delaying development.

In order to prevent the strong photographic effect of mercaptan, a thio-substituted pyrazolone coupler having a mercaptan compound having a diffusion-resistant group as a leaving group was published in Japanese Patent Publication No. 53-34044.
JP-A-54-80744 and JP-A-57-3585
However, these couplers do not have sufficient coupling activity and there are problems with the storage stability of the magenta dye produced, making it difficult to apply them to general color photographic materials.

Furthermore, JP-A-55-62454 describes a magenta coupler in which the 4-position of a pyrazolone derivative is substituted with R'-8- (R' represents a straight-chain or branched alkyl or aralkyl). In these couplers, the mercaptan compound that is released after coupling has virtually no development inhibitory effect, but the coupling activity of the puller is low, and the image storage stability, especially the light resistance, is poor. It had drawbacks such as.

6- Furthermore, JP-A No. 55-29805 discloses magenta in which the 4-position of a pyrazolone derivative is substituted with -8-OH- (, t, (-member 22) represents phthalimide, imidazole or benztriazole). couplers have been described, but these couplers do not have sufficient coupling activity;
Again, there is a problem with image preservation.

In addition, JP-A No. 57-4044 describes a bis-form magenta coupler with active point substitution components, but such magenta couplers have poor solubility in organic solvents, making them difficult to disperse and having poor color development. Inferior.

Furthermore, JP-A-57-17950 and JP-A-5
No. 8-205151 describes a magenta coupler in which the 3-position of 5-pyrazolone is substituted with an alkylamide group and the 4-position is substituted with a thioether group, but these couplers are chemically unstable and are susceptible to the presence of formalin. It has the disadvantage that if it is left in a place where it will be used before development, it will turn into a substance that does not develop color.

■ Purpose of the Invention The present invention has been made in view of the above-mentioned circumstances, and its first object is to provide a method that has sufficient reaction activity and that produces high yield without causing unnecessary fog or stain. The object of the present invention is to provide a silver halide color photographic material containing a novel two-equivalent magenta coupler that forms a dye.

A second object of the present invention is to provide a silver halide color photographic light-sensitive material in which the amount of silver halide in a photographic emulsion layer containing the novel two-equivalent magenta coupler and the amount of coupler used are reduced by using the novel two-equivalent magenta coupler. There is a particular thing.

A third object of the present invention is to provide a silver halide color photographic material that uses a new two-equivalent magenta coupler and has a robust dye image with excellent light resistance, heat resistance, and moisture resistance.

A fourth object of the present invention is to provide a silver halide color photographic material in which the active site substitution component of the coupler is eliminated during color development and does not react with silver halide to cause any adverse effects.

A fifth object of the present invention is to provide a silver halide color photographic light-sensitive material which has excellent storage stability and does not develop abnormal color during development even if it is left in a place where formalin exists before development.

■Specific structure of the invention As a result of research on various magenta couplers, the present inventors have developed a silver halide color photographic photosensitive material having at least one photographic constituent layer containing a magenta coupler represented by the following general formula on a support. The inventors have discovered that the above object can be achieved by using a material, and have completed the present invention.

In the general formula, the turtle represents an alkyl group or a cycloalkyl group, the turtle represents an alkyl group, an aryl group, or a heterocyclic group, and the bird represents a halogen atom, an alkyl group, an alkoxy group, an alkylthio group, an acylami 9-7 group. , represents an alkoxycarbonyl group, an alkylaminocarbonyl group or a dialkylaminocarbonyl group,
m represents an integer of θ to 4, n represents an integer of 1 to 2, and the nail represents an aryl group.

In the present invention, the alkyl group represented by the bird in the general formula is a straight-chain or branched alkyl group, preferably a straight-chain or branched alkyl group having 1 to 8 carbon atoms (e.g., methyl group, ethyl group). , propyl group, isopropyl group,
butyl group, isobutyl group, t-butyl group, amyl group, isoamyl group, hexyl group, octyl group, etc.). Among these, particularly preferred are i-subbutyl group and t-butyl group. This alkyl group can have a substituent,
Examples of substituents include hydroxyl group, hydroxycarbonyl group, cyano group, aryl group (e.g., phenyl group, tolyl group, etc.), alkyloxycarbonyl group (e.g., ethoxycarbonyl group, hexadecyloxycarbonyl group, etc.), aryloxycarbonyl group. groups (e.g., phenoxycarbonyl group, tolyloxycarbonyl group, naphthyloxycarbonyl group, etc.), alkylsulfonamide groups (e.g., methanesulfonamide group, etc.), acylamino groups (e.g.,
acetamide group, benzamide group, etc.), alkoxy group (
For example, methoxy group, benzyloxy group, etc.), aryloxy group (e.g. phenoxy group, etc.), sulfonyl group (
For example, a methanesulfonyl group, etc.) can be mentioned.

The cycloalkyl group represented by R in the above general formula is preferably a cycloalkyl group having 5 to 6 carbon atoms,
Examples include cyclopentyl group, cyclohexyl group, and the like. Among the alkyl groups and cycloalkyl groups represented by turtles, alkyl groups are preferred.

The alkyl group represented by the bird in the above general formula is a straight chain or branched alkyl group, preferably having 1 to 3 carbon atoms.
2 straight-chain or branched alkyl groups (e.g. methyl group,
(ethyl group, propyl group, octyl group, dodecyl group, hexadecyl group, etc.). These alkyl groups can have a substituent, and examples of this substituent include the same substituents as those described above when bird is an alkyl group.

The aryl group represented by the bird in the above general formula is, for example, a phenyl group, a naphthyl group, etc., and preferably a phenyl group. This aryl group can have a substituent, and examples of the substituent include a halogen atom (for example, a chlorine atom, a bromine atom, etc.), a hydroxyl group, a nitro group, a cyan group, a hydroxycarbonyl group, an alkyl group (direct A chain or branched alkyl group, such as a methyl group, ethyl group, propyl group, butyl group, amyl group, octyl group,
decyl group, dodecyl group, hexadecyl group, octadecyl group, etc.), alkoxy group (e.g., methoxy group, ethoxy group, propoxy group, butoxy group, pentyloxy group, octyloxy group, decyloxy group, dodecyloxy group, etc.), alkyl carbonyl Amino group (e.g., undecylcarbonylamino 7 group, dodecylcarbonylamino group, etc.)
, arylcarbonylamino group (e.g., naphthoylamide 7 group, toluoyl amino group, benzoylamino group, etc.)
, an alkylsulfonamide group (e.g., dodecylsulfonamide group, etc.), an arylsulfonamide group (e.g.,
(benzenesulfonamide group, etc.), alkylaminosulfonamide group (e.g., dimethylaminosulfonamide group, etc.), arylaminosulfonamide group (e.g., anilinosulfonamide group, etc.), alkylcarbamoyl group (e.g., hexadecylcarbamoyl group, etc.) (e.g., phenylcarbamoyl group, etc.), arylcarbamoyl group (e.g., phenylcarbamoyl group, etc.)
, sulfonyl group (e.g., methylsulfonyl group, n-dodecylsulfonyl group, etc.), alkyloxycarbonyl group (e.g., dodecyloxycarbonyl group, etc.), aryloxycarbonyl group (e.g., phenoxycarbonyl group, etc.), alkylsulfamoyl group (eg, N-methylsulfamoyl group, N,N-dimethylsulfamoyl group, etc.), arylsulfamoyl group (eg, phenylsulfamoyl group, etc.), and the like.

The heterocyclic group represented by the general formula ``bird'' is a 5-membered or 6-membered heterocyclic group.
For example, a 5-membered ring group and a 13-membered group include a chenyl group, a pyrrolyl group, a furyl group, a thiazolyl group, an imidazolyl group, a pyrazolyl group, a succinimide group, a triazolyl group, a tetrazolyl group, etc. Examples of the ring group include a pyridyl group, a pyrimidinyl group, a triazinyl group, a thiadiazinyl group, and a dithiazinyl group. These heterocyclic groups may further form a condensed ring with a benzene ring, and include, for example, a purinyl group, an imidazolyl group, a quinolyl group, an indolyl group, a phthalimide group, and the like.

When these heterocyclic groups have a substituent, examples of the substituent include the same substituents as the above-mentioned substituents when the bird is an aryl group.

The bird of the above general formula includes a halogen atom (e.g., chlorine, bromine, fluorine, etc.), an alkyl group (e.g., methyl group, ethyl group, propyl group, butyl group, t-butyl group, octyl group, t-octyl group, dodecyl group, hexadecyl group, etc.),
Alkoxy groups (e.g., methoxy, ethoxy, propyloxy, 180-propyloxy, butyloxy, 1-14-butyloxy, etc.), alkylthio groups (e.g., methylthio, ethylthio, butylthio, octylthio, etc.) ), acylamino group (e.g., acetamide group, ethanamide group, butanamide group, butoxycarbonyl group,
octyloxycarbonyl group, dodecyloxycarbonyl group, etc.), alkylaminocarbonyl group (e.g., ethylcarbamoyl group, propylcarbamoyl group, butylcarbamoyl group, octylcarbamoyl group, dodecylcarbamoyl group, etc.), dialkylaminocarbonyl group (e.g., N, N-dimethylcarbamoyl group, etc.).

The alkyl group, alkoxy group, alkylthio group, acylamino group, alkoxycarbonyl group, alkylaminocarbonyl group, and dialkylaminocarbonyl group represented by the above general formula may have a substituent. Examples of the substituent include the same substituents as those described above when the name in the general formula is an alkyl group.

m in the general formula represents an integer of θ to 4, preferably 1 to 2. Further, n represents an integer of 1 to 2.

The horse in the above general formula is bonded to the phenyl group via the -80,N)I- group, and when n is 1, the bonding position is the phenylthio group bonded to the 4-position of the pyrazolone ring. It can be at any position relative to the sulfur atom, preferably at the meta position. Further, when n is 2, preferably it is the ortho position and the meta position.

The position where R in the above general formula is bonded to the phenyl group is any position relative to the sulfur atom of the phenylthio group bonded to the 4-position of the pyrazolone ring.

The above Rt80fNH group and bird are mutually ortho, meta,
It may be in any para position, preferably in the para position.

The aryl group represented by red in the above general formula is, for example, a phenyl group, a naphthyl group, etc., and preferably a phenyl group. This aryl group can have a substituent, and examples of the substituent include a halogen atom (e.g., fluorine atom, chlorine atom, bromine atom, etc.), a hydroxyl group, a nitro group, a cyano group, an alkyl group (e.g., methyl group, trifluoromethyl group, butyl group, cyanomethyl group, etc.), aryl group (e.g., phenyl group, tolyl group, naphthyl group, etc.), alkyloxy group (e.g., methoxy group, benzyloxy group, etc.), aryloxy group ( For example, phenoxy group, etc.), hydroxycarbonyl group, alkyloxycarbonyl group (e.g., ethoxycarbonyl group, etc.), aryloxycarbonyl group (e.g., phenoxycarbonyl group, etc.), alkylsulfonyl group (e.g., methylsulfonyl group, ethylsulfonyl group, etc.) , propylsulfonyl group, dodecylsulfonyl group, etc.), arylsulfonyl group (
(e.g., phenylsulfonyl group, etc.), alkylacyloxy group (e.g., acetyloxy group, cyclohexylcarbonyloxy group, etc.), arylacyloxy group (e.g., benzoyloxy group, etc.), alkylami7 group (e.g., ethylamino group, dimethyl amino group, jetanolamino group, etc.)
, arylamino group (e.g., anilino group, etc.), alkylcarbamoyl group (e.g., ethylcarbamoyl group, etc.)
, arylcarbamoyl group (e.g., phenylcarbamoyl group, etc.), alkanamide group (e.g., acetamide group, etc.), arylacylamino group (e.g., benzamide group, etc.), alkylsulfonamide group (e.g., methylsulfonamide group, ethylsulfonamide group, etc.) group), arylsulfonamide group (e.g., benzenesulfonamide group, etc.), alkylsulfamoyl group (e.g., N-methylsulfamoyl group, N,N-dimethylsulfamoyl group, etc.), arylsulfamoyl group (For example, phenylsulfamoyl group, etc.). Preferred among these substituents is a halogen atom.

When the aryl group represented by Ar has a substituent,
This substituent may have one or more, preferably one or two, and these substituents may be the same or different.

=18- In the case where Mr in the above general formula has a substituent, when there is one substituent, this substituent can be placed at any position relative to the nitrogen atom at position 1 of the pyrazolone ring to which the aryl group is bonded. , preferably at the 2- or 4-position. Furthermore, when the aryl group represented by ^r, for example, the phenyl group, has two substituents, the positional relationship between these two substituents may be in the ortho, meta, or para positions, but It is preferable that the substituent is bonded to the 2-position relative to the nitrogen atom of the pyrazolone ring.

Typical specific examples of the magenta coupler of the present invention represented by the above general formula are shown below, but the present invention is not limited thereto.

Exemplary Compound 11 20- 21- -26- -27- The magenta coupler of the present invention represented by the above general formula is:
It can be synthesized by applying conventionally known methods.

In particular, the following synthetic methods are available for introducing a thio group as a leaving group into the 4-position of pyrazolone. That is, according to the method for synthesizing a DIR magenta coupler having an arylthio group or a heterocyclic 29-thio group as a leaving group described in U.S. Pat. A method of reacting phenyl chloride with an equivalent pyrazolone coupler having an active methylene group, as described in JP-A-49-62464, the 4-position of the pyrazolone coupler is dibrominated and about 3
Method for reacting with twice the molar amount of mercaptan, Research Disclosure
ure) 13806 (1975), in which bromine is added dropwise in the presence of a 14-equivalent pyrazolone coupler and a mercaptan.

Typical synthesis examples of the magenta coupler represented by the above general formula of the present invention will be described below, but the present invention is not limited thereto.

Synthesis Example 1 Synthesis of Exemplary Coupler (7) 1-(2,3-dichlorophenyl)-3-isobutanamide-5-pyrazolone 311i and 5-(4-dodecyloxybenzenesulfonamide)-2-ethoxyphenylmercaptan 49Ii were combined with dimethyl Formamide (DMF
)20011j, and bromine 16F was added dropwise thereto. After dropping, the mixture was heated to 70°0 and reacted for 2 hours. The reaction solution was poured into 1 liter of ice water to precipitate a solid. The solid was filtered, washed with water, and then recrystallized from toluene to give the illustrative coupler (
7) Obtained 321. The FD mass spectrum of the obtained coupler is M/e = 806 (M+), and the melting point is 125.
~129°C.

Synthesis Example 2 Synthesis of exemplified coupler 1-(2,3-dichlorophenyl)-3-isobutanamido-5-pyrazolone 31g and 2-dodecyloxy-5
-Methanesulfonamidophenylmercaptan 36Ii
@Dissolved in 200m of DMF and added 161 bromine to it! was dripped. After dropping, the mixture was heated to 70°0 and reacted for 2 hours. The reaction solution was poured into 1 liter of ice water to precipitate a solid. The solid was filtered, washed with water, and then recrystallized from toluene to obtain 41 g of the exemplary coupler. The FD mass spectrum of the obtained coupler is M/e = 667 (M+), and the melting point is 1
It was 03-107°0.

In order to produce silver halide color photographic materials,
The magenta couplers of the present invention may be used alone or in combination of two or more. Furthermore, the magenta coupler of the present invention and a conventionally known magenta coupler can be used in combination.

Incorporation of the magenta coupler of the present invention into a photographic constituent layer of a silver halide color photographic light-sensitive material is carried out according to a conventionally known method. That is, the coupler of the present invention may be dibutyl phthalate, dioctyl phthalate, triphenyl phosphate, tricresyl phosphate, dioctyl butyl phosphate, N,N-diethyl caprylamide,
High boiling point organic solvents that are immiscible with water such as N,N-diethyl laurylamide and N,N-dibutyl laurylamide, or low boiling point organic solvents such as ethyl acetate and butyl acetate, or methanol, ethanol, acetone, dioxane, tetrahydrofuran, etc. or in a high-boiling water-immiscible organic solvent and/or a low-boiling organic solvent and/or a water-soluble organic solvent. .

Although the timing of addition to the photographic emulsion is arbitrary, it is usually preferable to add it to the emulsion after the second ripening is completed.

As used herein, the term "layer structure" refers to light-sensitive layers and non-light-sensitive layers such as interlayers, subbing layers, antihalation layers, protective layers, and filter layers of silver halide emulsions. The magenta coupler of the present invention is contained in at least one of the photographic constituent layers constituting the photosensitive layer and the non-photosensitive layer, but is preferably contained in the photosensitive layer consisting of a silver halide emulsion layer.

When the coupler of the present invention is contained in a silver halide emulsion layer, the content is usually 0.000.
0.007 to 0.7 mol, preferably 0.01 to 0.1 mol. Further, when the coupler of the present invention is contained in the non-photosensitive layer, the content is 0.00 per 1111' of gelatin.
1 to 10 mmol, preferably 0.1 to 0.01 mmol.

It is advantageous to use surfactants to help finely disperse the coupler solution or dispersion in the hydrophilic colloid used in the photographic emulsion.

After the coupler is dissolved in a suitable organic solvent, it is mixed with an aqueous gelatin solution containing a surfactant, then emulsified and dispersed in a high-speed rotary mixer or colloid mill, and then added directly into the silver halide emulsion, or After setting the dispersion liquid, it may be chopped, and after removing the low boiling point organic solvent by means such as washing with water, it may be added to the silver halide emulsion. The magenta coupler of the present invention can also be added by the Fischer dispersion method.

Examples of the surfactant that can be used in the present invention include alkylbenzene sulfonates, alkylnaphthalene sulfonates, alkyl sulfonates, alkyl sulfates, alkyl phosphates, sulfosuccinates, and sulfoalkyl polyesters. Anionic surfactants such as oxyethylene alkylphenyl ethers, nonionic surfactants such as steroidal saponins, alkylene oxide derivatives and glycidol derivatives, amino acids, aminoalkylsulfonic acids, alkyl betaines, etc. Amphoteric surfactants and cationic surfactants such as quaternary ammonium monosalts can be used. Specific examples of these surfactants can be found in “Surfactant Handbook” (Sangyo Tosho, 19
1966) and [Emulsifier/Emulsifier, Research/Technical Data Collection]
(Science Panronsha, 1978).

Other known magenta couplers may be used in the silver halide color photographic material using the magenta coupler according to the present invention, if necessary. Specific examples of such known magenta couplers include pyrazolone-based, pyrazolotriazole-based, pyrazolinobenzimidazole-based, and indasilone-based couplers. Such a magenta coupler is disclosed in U.S. Pat. No. 2,600,7
No. 88, No. 2,983,608, No. 3,062,65
No. 3, No. 3,127,269, No. 3,311,476
No. 3,419,391, No. 3,519.429, No. 3,558,319, No. 3,582,322,
No. 3,615,506, No. 3,834,908, No. 3,891,445, West German Patent No. 1,810.464, West German Patent Application (OL8) No. 2,408,665, No. 2
, 417°945, 2,418,959, 2,
No. 424,467, Japanese Patent Publication No. 40-6031, Japanese Patent Publication No. 5
No. 1-20826, No. 52-58922, No. 49-1
No. 29538, No. 49-74027, No. 50-159
No. 336, No. 52-42121, No. 49-74028
No. 50-60233, No. 51-26541, No. 53-55122, and Japanese Patent Application No. 110943/1983.

Among these magenta couplers, colored magenta couplers include compounds in which the active site of a colorless magenta coupler is arylazo-substituted or heteroarylazo-substituted.
No. 608, No. 2,455,170, No. 2.725,2
No. 92, No. 3,005,712, No. 3,519,42
No. 9, No. 2,688,539, British Patent No. 800,2
No. 62, No. 1,044,778, Belgian Patent No. 67
Examples include compounds described in No. 6.691 and the like.

The silver halide color photographic light-sensitive material applied to the present invention may contain other dye-forming couplers 36--, such as yellow couplers and cyan couplers, in addition to the magenta coupler of the present invention in order to form multicolor images. can. Yellow couplers that can be used together with the magenta coupler of the present invention include benzoylacetanilide-type and pivaloylacetanilide-type yellow couplers, and 2 in which the carbon atom at the coupling position is further substituted with a substituent that can be separated during the coupling reaction. Mention may be made of equivalent yellow couplers.

A specific example of a yellow coupler that can be used in the present invention is U.S. Pat.
87 Milk No. 057, No. 3,265,506, No. 3,40
8.194, 3,551,155, 3,582
, No. 322, No. 3,725,072, No. 3,891,
No. 445, West German Patent No. 1,547,868, West German Application No. 2,219,917, No. 2,261,161, No. 2,414,006, British Patent No. 1,425,020, Japanese Patent Publication No. No.-10783, JP-A-47-26133
No. 48-73147, No. 51-102636,
No. 50-6341, No. 50-123342, No. 50
-130442, 51-21827, 50-8
No. 7650, No. 52-82424, No. 52-1152
No. 19, No. 58-95346, etc.

In addition, cyan couplers include phenol or naphthol derivatives, and colored cyan couplers include arylazo-substituted phenoxy groups directly or via an alkoxy group at the coupling position of colorless cyan couplers. Mention may be made of substituted compounds.

Examples of such cyan couplers include, for example, U.S. Pat. No. 2,423,730, U.S. Pat.
Same No. 3,476,563.

No. 3,737,326, No. 3,758,308, No. 3,893゜044, JP-A-47-3
No. 7,425 1% 1972-10.135, JP 1977-1987
No. 0-25,228, JP-A-50-112.038,
JP-A-50-117,422 and JP-A-50-13
This includes those described in Publication No. 0,441, etc. Also, as a colored cyan coupler as a masking coupler, for example, U.S. Patent No. 2.521,908
No. 3,034,892, British Patent No. 1.255
, No. 111, JP-A-48-22028, and the like.

Furthermore, U.S. Patent No. 3,476,563 and Japanese Patent Application Laid-open No. 1987-1
Colored cyan couplers of the type in which the dye flows out into the processing bath by reaction with the oxidation product of a color developing agent, such as those described in No. 0135 and No. 50-123341, can also be used.

The above-mentioned yellow and cyan couplers other than the magenta couplers of the present invention are generally used in an amount of 0.0% per mole of silver halide in the emulsion layer.
007 mol-0, fumol, preferably 0.01 mol to 0
．． Use 1 mole.

Furthermore, for the purpose of improving the sharpness, graininess, etc. of color images, so-called competing couplers, development inhibitor-releasing couplers (so-called DIR couplers), or developing agents that do not form a dye by reaction with an oxidized form of a developing agent are used. It is also possible to use inhibitor-releasing substances. These may be used alone or in combination of two or more.

Moreover, the magenta coupler of the present invention is disclosed in Japanese Patent Publication No. 49-265
No. 85, U.S. Patent No. 3,486,890, Research Disc.
It can also be used in the dye image forming methods described in US Pat. That is,
The magenta coupler of the present invention and the aromatic primary amine developing agent are both contained in a light-sensitive material, and after imagewise exposure, color development is carried out by processing with an alkaline bath, black and white developer, or heat treatment, A dye image with uniform gradation can be obtained.

The silver halide color photographic light-sensitive material applied to the present invention basically consists of a support and a light-sensitive emulsion layer, but depending on the type of silver halide color photographic light-sensitive material, a subbing layer, an intermediate layer, Generally, photographic constituent layers consisting of non-photosensitive layers such as a filter layer, an antihalation layer, an anticurl layer, a backing layer, and a pupil retaining layer are appropriately combined and layered. In addition, the photosensitive layers constituting the photographic constituent layers include, for example, layers containing relatively high-sensitivity silver halide that are spectrally sensitized to the same wavelength range or different wavelength ranges, and relatively low-sensitivity silver halide layers. A plurality of layers containing layers may be stacked. This multiple layer may be composed of three layers each having a different sensitivity, and further,
A non-photosensitive layer may be provided between these photosensitive layers.

The photographic constituent layer containing the coupler of the present invention contains a reducing agent = 40- or an antioxidant, such as sulfite (sodium sulfite, potassium sulfite, etc.), bisulfite (sodium bisulfite, potassium bisulfite, etc.), hydroxylamine. (Hydroxylamine, N-methylhydroxylamine, N
- phenylhydroxylamine, etc.), sulfinic acids (
sodium phenylsulfinate, etc.), hydrazines (
N, W-dimethylhydrazine, etc.), reductones (ascorbic acid, etc.), aromatic hydrocarbons having one or more hydroxyl groups (p-aminephenol, gallic acid, catechol, pyrogallol, resorcinol, 2゜3-dihydroxynaphthalene) etc.), which is preferable in order to fully exhibit the effects of the present invention.

In order to further increase the stability of the dye image formed,
Alkyl-substituted hydroxynes and their alkoxy derivatives, bishydroxynes, polymeric hydroquinones, etc. may be contained singly or in combination in the photographic constituent layer containing the coupler of the present invention or in a layer adjacent thereto.

Furthermore, p-alco-41-oxyphenols, 6-chromanol, 6,6'-dihydroxy-2,2'-spirochroman and their alkoxy or acyloxy derivatives can also be used.

The silver halide color photographic light-sensitive material according to the present invention contains benzotriazoles, triazines, benzophenone compounds, or acrylonitrile as an ultraviolet absorber in its photographic constituent layers (for example, protective layer, intermediate layer, emulsion layer, back layer, etc.). It may contain a system compound.

To form a photosensitive material, silver halide is dispersed in a suitable protective colloid to constitute a photosensitive layer, which and other non-photosensitive layers such as intermediate layers, protective layers, filter layers, etc. Protective colloids used in photographic constituent layers include alkali-treated gelatin, low-acid-treated gelatin, derivative gelatin, colloidal albumin, cellulose derivatives, and synthetic resins such as polyvinyl alcohol and polyvinylpyrrolidone. Used alone or in combination.

The silver halide color photographic light-sensitive material according to the present invention is produced by coating it on a support that has good flatness and exhibits little dimensional change during the production process or processing.

In this case, the support may be a plastic film, plastic laminated paper, baryta paper, synthetic paper, or even a hard material such as a glass plate, metal, or ceramic.

These supports can be subjected to various surface treatments such as hydrophilic treatment for the purpose of improving adhesion with the photographic emulsion layer, such as saponification treatment, corona discharge treatment, subbing treatment, and setting treatment. Processing such as the following is performed.

The silver halide emulsion used in the silver halide color photographic light-sensitive material according to the present invention is usually prepared by combining a water-soluble complex salt (for example, silver nitrate) solution and a water-soluble halide salt (for example, potassium bromide) solution with a water-soluble polymer such as gelatin. It is made by mixing in the presence of a solution.

The silver halide may be any halogen compound used in ordinary silver halide photographic materials such as silver chloride, needle bromide, silver iodide, silver chlorobromide, silver iodobromide, silver chloroiodobromide, etc. Silver can be used.

These silver halide emulsions are prepared according to known and conventional methods (for example, single or double jet method, controlled double jet method, etc.). Furthermore, two or more types of silver halide photographic emulsions formed separately may be mixed.

Furthermore, even if the crystal structure of silver halide grains is uniform inside, there are also grains with a layered structure with different interior and exterior layers, so-called conversion emulsions, Lippmann emulsions, covered grain emulsions, or grains that have been optically or It may also be chemically fogged.

Further, either a type in which a latent image is mainly formed on the surface or an internal latent image type in which a latent image is formed inside the particle may be used. These photographic emulsions are produced using the generally accepted ammonia method,
It can be prepared by various methods such as a neutral method and an acidic method. Further, the type of silver halide, content and mixing ratio of silver halide, average grain size, size distribution, etc. are appropriately selected depending on the type and use of the photographic light-sensitive material.

The above silver halide emulsion can be 44-sensitized with a chemical sensitizer. Chemical sensitizers include noble metal sensitizers (potassium aurithiocyanate, ammonium chlorovaladate, potassium chloroplatinate, etc.), sulfur sensitizers (allylthiocarbamide, thiourea, cystine, etc.), and selenium sensitizers (active and inactive). They are broadly classified into four types: active selenium compounds, etc.) and reduction sensitizers (stannic salts, polyamines, etc.). Silver halide emulsions can be chemically sensitized using these sensitizers alone or in combination as appropriate.

Furthermore, the photographic emulsion according to the present invention may contain cyanine,
Spectral sensitization or superchromatic sensitization can be performed by using cyanine dyes such as merocyanine and carbocyanine alone or in combination, or by using them in combination with styryl dye or the like.

These color sensitization techniques have been known for a long time, and the selection of the combination of dyes is determined arbitrarily depending on the wavelength range to be sensitized, sensitivity, etc., and the purpose and use of the silver halide color photographic light-sensitive material. Is possible.

The above silver halide emulsion contains silver halide color 45--1-phenyl-5 to prevent a decrease in sensitivity and the occurrence of fog during the manufacturing process, storage, or processing of photographic light-sensitive materials.
-mercaptotetrazole, 3-methylbenzothiazole, 4-hydroxy-6-methyl-1,3,3a,7-
Various compounds such as heterocyclic compounds such as tetrazaindene, mercapto compounds, metal salts, etc. can be added.

Hardening of the emulsion is carried out according to conventional methods. The hardeners used are conventional photographic hardeners, such as aldehyde compounds such as formaldehyde, glyoxal, and glutaraldehyde, and rust conductor compounds such as their acetals or sodium bisulfite adducts, as well as methanesulfonic acid esters. Compounds, mucochloric acid, mucohalogenated compounds, epoxy compounds, aziridine compounds, active halogen compounds, maleic acid imide compounds, active vinyl compounds, carbonimide compounds (isoxazole compounds, N-methylol compounds) , isocyanate-based compounds, or inorganic hardeners such as chromium ammonium and zirconium sulfate.

A surfactant may be added alone or in combination to the above silver halide emulsion. They are coating aids, emulsifying and dispersing agents,
It is used for sensitization, improvement of photographic properties, prevention of static electricity, prevention of adhesion, etc. These surfactants include natural surfactants such as saponin, alkylene oxide type, glycerin type,
Nonionic surfactants such as glycidol, higher alkylamines, quaternary ammonium salts, pyridine, other heterocycles, cationic surfactants such as phosphonium or sulfonium, carboxylic acids, sulfonic acids, phosphoric acids, sulfuric acids They are divided into anionic surfactants containing acidic groups such as ester groups and phosphoric acid ester groups, and amphoteric surfactants such as amino acids, aminosulfonic acids, and sulfuric acid or phosphoric acid esters of amino/alcohols.

The formation of color photographic images of the present invention is realized in various forms of light-sensitive materials. One method is to process a light-sensitive material having a silver halide emulsion layer containing a diffusion-resistant coupler on a support with an alkaline developer containing an aromatic primary amine color developer to make it water-insoluble or resistant. This method leaves a diffusible dye in the emulsion layer. In another form, a light-sensitive material having a silver halide emulsion layer in combination with a diffusion-resistant coupler on a support is processed with an alkaline developer containing an aromatic primary amine color developing agent into an aqueous medium. A soluble and diffusible dye is formed and transferred to an image-receiving layer consisting of another hydrophilic colloid.

That is, it is a diffusion transfer color type.

The silver halide color photographic light-sensitive material of the present invention includes all kinds of silver halide color photographic light-sensitive materials such as color negative films, color positive films, color reversal films, and color papers.

An embodiment of the silver halide color photographic light-sensitive material according to the present invention includes a green-sensitive silver halide emulsion layer containing the magenta coupler of the present invention, a blue-sensitive silver halide emulsion layer containing a yellow coupler, and a cyan coupler. There is a multilayer, multicolor silver halide photographic material having a red-sensitive silver halide emulsion layer on a support. Known blue-sensitive copper halide emulsions, green-sensitive silver halide emulsions, and red-sensitive silver halide emulsions in such light-sensitive materials can be appropriately used.

After exposure of the silver halide color photographic material according to the present invention, a color image can be obtained by a commonly used color development method. The basic steps in the negative-positive method include color development, bleaching, and fixing steps. The basic steps in the reversal method include development with a first developer, followed by exposure to white light or treatment with a bath containing a fogging agent, color development, bleaching, and fixing steps.

Each of these basic steps may be performed independently, or two or more steps may be performed in a single treatment using a processing liquid that has these functions. For example, one-bath color processing methods containing a color developing agent, a ferric salt bleaching component and a thiosulfate fixing component, or iron ethylenediaminetetraacetate.
There is a one-bath bleach-fixing method containing a complex salt bleaching component and a thiosulfate fixing component.

49- Furthermore, each step can be divided into two or more processes as necessary, or a combination of processes such as color development, first fixing, and bleach-fixing is also possible. Incidentally, in the development process, the above-mentioned various processes such as a pre-hardening bath, a neutralization tower, an image stabilizing bath, and water washing are combined as necessary. Processing temperature is 8°a
Although it may be less than 18゛O in many cases. The range of 20°0 to 60°0 is particularly frequently used.

A temperature of about 30°C to 60°C is suitable for rapid processing. Note that it is not necessary that the set temperatures for the series of treatment steps be the same.

The color developing solution is an alkaline aqueous solution containing a developing agent and having a pH of 8 or more, preferably 9 to 12. The above-mentioned developing agent refers to a compound having a -grade amino group on an aromatic ring and capable of developing exposed silver halide, or a precursor for forming such a compound. Preferred are p-phenylene diamines, for example 4-amino-N1
．． N-diethylaniline, 3-methyl-4-amino-N
, IN-diethylaniline, 4-amino-N-ethyl-
N-fi-hydroxyethylaniline, 3-methyl-4
-amino-N-ethyl-N-p-hydroxyethylaniline, 3-methyl-4-amino-N-ethyl-N-fi
-Methanesulfonamidoethylaniline-N-β-methoxyethylaniline, 3-β-methanesulfonamidoethyl-4-amino-N. , N-diethylaniline, 3-methoxy-4-amino-N-ethyl-N
-fi-hydroxyethylaniline, 3-methoxy-4
-amino-N-ethyl-N-11methoxyethylaniline, 3-acetamido-4-amino-N,,,N-
Diethylaniline, 4-amino-N,N-dimethylaniline, N-ethyl-N-#-C I-(II-methoxyethoxy)ethoxy]ethyl-3-methyl-4-aminoaniline, N-ethyl-N-fi- (β-methoxyethoxy)ethyl-3-methyl-4-aminoaniline,
These salts include sulfates, hydrochlorides, sulfites, p-toluenesulfonates, and the like.

Various additives are added to the color developing solution as necessary. Main examples include alkaline agents (e.g. alkali metal and ammonium hydroxides, carbonates, phosphates, etc.), pH adjusting or buffering agents (e.g. weak acids and bases such as acetic acid and boric acid, and their salts). , development accelerators (for example, pyridinium compounds, cationic compounds, potassium nitrate, sodium nitrate, polyethylene glycol condensates and their derivatives, nonionic compounds such as polythioethers,
Polymer compounds with sulfide esters, lysine, organic amines such as ethanolamine, benzyl alcohol, hydrazines, etc.), antifoggants (such as alkali bromides, alkali iodides, nitrobenzimidazoles, mercaptobenzimidazole, 5-
Methylbenzotriazole, 1-phenyl-5-mercaptotetrazole, compounds for quick processing liquids, thiosulfonyl compounds, phenazine N oxides, benzothiazolium nitrobenzoate derivatives, etc.), stain or sludge inhibitors, genus 1 effects Accelerators, preservatives (e.g. sulfites,
acid sulfites, hydroxylamine hydrochloride, form sulfide, alkano-52-ylamine sulfite adducts, etc.).

A silver halide color photographic light-sensitive material containing the coupler of the present invention can be subjected to color development processing without impairing its practicality even in the presence of a competing coupler such as citradinic acid.

After the color development process, the silver halide color photographic light-sensitive material according to the present invention can be subjected to a bleaching process in a conventional manner.

This treatment may be done simultaneously with fixing or separately. This processing solution can also be used as a bleach-fixing bath by adding a fixing agent if necessary.

Various compounds are used as bleaching agents, among which red blood salts; dichromate; iron (2), cobalt (2)
, polyvalent metal compounds such as copper alloys, in particular complex salts of these polyvalent metal cations and organic acids, such as aminopolycarboxylic acids such as ethylenediaminetetraacetic acid, nitrilotriacetic acid, diaminopropaturatetraacetic acid, citric acid, tartaric acid,
Metal complexes such as malic acid, peracids such as alkyl peracids, persulfates, permanganates, hydrogen peroxide, hypochlorites such as chlorine, bromine, saran powder, etc.
- or a suitable combination is common. Furthermore, various additives including a bleaching accelerator can also be added to this processing solution.

After the color development process, conventional photographic processing is carried out, such as a stop solution containing an organic acid, a stop fix solution containing an organic acid and a fixing component such as hypo or ammonium thiosulfate, a fixing solution containing a fixing component such as hypo or ammonium thiosulfate, Bleach solutions containing ferric salts of aminopolycarboxylic acids and alkali halides as main components, bleach-fix solutions containing ferric salts of aminopolycarboxylic acids and fixing components such as hypo or ammonium thiosulfate, and other stabilizing solutions. It is sufficient to carry out an appropriate combination of treatments selected from treatments using treatment liquids such as the above, washing with water and drying, and the like.

The coupler according to the present invention has a silver halide content in the emulsion that is several times smaller than that of ordinary silver halide light-sensitive materials.
It can also be used in photosensitive materials with a low silver content, ranging from 1/100 to 1/100.

For color photosensitive materials with a reduced amount of silver halide in this way, there is a development processing method in which the developed silver produced by color development is subjected to halide bleaching, and then color development is performed again to increase the amount of produced dye, peroxide, cobalt, etc. A sufficient dye image can be obtained by applying a development method using color intensification using complex salts or sodium chlorite.

The halogenated color silver photographic light-sensitive material of the present invention may contain the above color developing agent in the hydrophilic colloid layer, either as the color developing agent itself or as its precursor. A color developing agent precursor is a compound that can form a color developing agent under alkaline conditions;
Examples include Schiff-Pace type precursors with aromatic aldehyde derivatives, polyvalent metal ion complex precursors, phthalic acid imide derivative precursors, phosphoric acid amide derivative precursors, sugar amine reactant precursors, and urethane type precursors. Precursors for these aromatic primary amine color developing agents are described, for example, in U.S. Pat.
No. 42,599, No. 2,507,114, No. 2.
No. 695.234, No. 3,719,492, British Patent No. 803,783, JP-A-53-13562
No. 8, Publications No. 54-79035, Research Disclosure Magazine No. 15159, No. 12146, No. 1
No. 3924.

These aromatic primary amine color developing agents or their precursors need to be added in amounts that will provide sufficient color development during development. This amount varies depending on the type of photosensitive material, but it is generally photosensitive silver halide 1
Between 0.1 and 5 moles per mole, preferably 0.5
It is used in a range of mol to 3 mol. These color developing agents or their precursors can be used alone or in combination. In order to incorporate the above compound into a photographic light-sensitive material, it can be dissolved in a suitable solvent such as water, methanol, ethanol, acetone, etc., and added. It can be added as an emulsified dispersion using a boiling point organic solvent or as a 56-impregnated latex polymer as described in Research Disclosure No. 14850.

(2) Specific Examples of the Invention Next, the present invention will be concretely explained based on practical examples, but the embodiments of the present invention are not limited thereby.

Example 1 Exemplary couplers (1), (71,0υ, 01) and the following comparative couplers ((trans) to (G) each containing 2 x 10-'' moles of tricresyl phosphate) 15@t and ethyl acetate 3
Alkanol B
(Alkylnaphthalene sulfonate, manufactured by DuPont) 1
．． The mixture was mixed with 300 g of a 5% gelatin aqueous solution and emulsified and dispersed in a colloid mill. A photographic emulsion 1 containing a dispersion of this coupler, 0.2 mol of green-sensitive silver iodobromide (6 mol % silver iodide, 94 mol % silver bromide) and 40.9 mol gelatin
- and 20% solution of 1,2-bis(vinylsulfonyl)ethane was added as a hardening agent, and the mixture was coated on a cellulose triacetate film base and dried. A gelatine protective layer was applied on this layer to prepare silver halide color photographic photosensitive material samples (1) to afJ. The amount of silver applied to each sample at this time was 21/d. After each of these samples was wedge exposed using a conventional method, the samples were processed using the following processing steps and the processing liquid composition shown below.

[Processing process (38°0)] Color development 3 minutes 15 seconds Bleaching 6 minutes 30 seconds Washing with water 3 minutes 15 seconds Fixing 6 minutes 30 seconds Washing with water 3 minutes! 5 seconds stabilizing bath 1 minute 30 seconds [Color developer composition] 4-amino-3-methyl-N-ethyl-N-(/1-hydroxyethyl)-aniline sulfate 4,75jl anhydrous sodium sulfite 4,2511 hydroxylamine /
//! Sulfate 2. OIi Anhydrous Potassium Carbonate 37.5
N Sodium bromide 1.3I Nitrilotriacetic acid trisodium salt (monohydrate) 2.5
II Potassium Hydroxide 1. O# Add water to 11 and use potassium hydroxide to pH 10.
, adjust to 0.

[Bleach solution composition]

Ethylenediaminetetraacetic acid ammonium salt 100
, OIi Ethylenediaminetetraacetic acid diammonium salt 10.0 g Ammonium bromide iso, ofI Glacial acetic acid 10. - Add water to 11 and adjust pH to 6.0 using aqueous ammonia.

[Fixer composition]

Ammonium thiosulfate 175. ON Anhydrous sodium sulfite 8.6I Sodium metasulfite 2.3y Add water to make 1j, and adjust to pH 6.0 using acetic acid.

[Stabilizing liquid composition]

Formalin (37% aqueous solution) 1.5aj Konidax (manufactured by Konishiroku Photo Industry Co., Ltd.) r, 5- Add water and 1
Set to 1.

The magenta dye image obtained above was measured using a densitometer (FD-
7R (manufactured by Konishiroku Photo Industry Co., Ltd.) using green light, the color development sensitivity (expressed as a relative value when the sensitivity in sample an is set to 100), capri, and maximum density were calculated, and the results were summarized in the following table. It is shown in Table 1.

Table 1-160 - From the results shown in Table 1 above, samples (1), (2), (3), and (4) using the couplers of the present invention are compared to samples (5) to 2 using the comparative couplers. It can be seen that it has higher color development sensitivity and maximum density than I, and also shows improved color development performance with no increase in fog.

Comparative coupler ((trans)(U.S. Patent No. 3.227.554)
Comparative coupler (B) (Special Publication No. 1983-3
4044) (2 61- Comparative coupler (C) (compound described in JP-A No. 54-89744) Comparative coupler ■) (compound described in JP-A-55-29805) Comparative coupler country) (JP-A-55-29805) Showa 55-624
Compound described in No. 5) t Comparative coupler (F) (compound described in JP-A-57-4044) Comparative coupler (G1 (compound described in JP-A-57-3585)) Example 2 Prepared in Example 1 A durability test was conducted using the dye image samples of Samples +11 to Q0.That is, after the durability test, the above samples were left at 80°C and 40% R, H for 2 weeks.Also, the light resistance test The sample was treated with a xenon fade meter (6KW) for 100 hours.Furthermore, the moisture resistance test was conducted at 60℃, 80%R, H
, the sample was left for 4 weeks.

These samples were measured using green light, and the dye residual rate M was calculated.

Here, the dye residual rate is expressed as a percentage of the density after the durability test in the exposed area where the dye density before the durability test is 1.0. In addition, regarding heat resistance and light resistance, the area with a density of 1.0 was simultaneously measured using blue light, and the yellow staining rate (maximum) (density after durability test / density before durability test ×
1oo) was calculated.

The results obtained are shown in Table 2.

Margin below 64- Table 2 From the results shown in Table 2, samples (11, +21, (3) and (4)) using the coupler of the present invention are different from samples (5) to I using the comparative coupler. In comparison, the occurrence of yellow staining is small, so it can be seen that the coupler according to the present invention is an excellent coupler that is stable in terms of durability and does not easily cause a decrease in image density even during storage.

65- Example 3 After applying the samples +11 to an created in Example 1, the samples were left unexposed in a sealed container containing 1% formaldehyde aqueous solution in a dark room for 3 days without contact with the solution. did. These samples and an untreated sample for comparison were exposed and developed in the same manner as in Example 1, the sensitivity and maximum density were measured, and the Polmarin resistance (T) (treated sample/untreated sample xioo) was calculated. The results obtained are shown in Table 3.

From the results shown in Table 3 in the margin below, samples (1) to (4) using the couplers of the present invention are different from samples (5) to (4) using the comparative couplers.
(Compared to ID, this coupler is less susceptible to negative effects such as decreased sensitivity and decreased maximum concentration due to formalin, and has excellent properties for preserving raw samples.)

Example 4 5 X 10-'' moles each of exemplified couplers (4), (8), α→, (a) and the following comparative couplers (6), (I) were added to tricresyl phosphate 4 and ethyl acetate 12 m
1. Heat and dissolve this solution in the mixture of alkanol B (
Alkylnaphthalene sulfonate (manufactured by DuPont) 1.
The mixture was mixed with 70 mg of a 5% gelatin aqueous solution containing 511, and emulsified and dispersed using a colloid mill. A dispersion of this coupler was mixed with 1 part of a photographic emulsion containing 0.2 mol of green-sensitive silver iodobromide (6 mol% silver iodide, 94 mol% silver bromide) and 30.9 mols of gelatin, and used as a hardening agent. A 2% solution of 1,2-bis(vinylsulfonyl)ethane 201 was added, coated on a cellulose triacetate film base, and dried. A gelatin protective layer was coated on this layer to prepare a sample sample (L7) of a silver halide color photographic light-sensitive material. The amount of silver applied to each sample at this time was If//wl. These samples were each subjected to wedge exposure using a conventional method, and then subjected to the same treatment using the treatment solution used in Example 1. The magenta dye image obtained through this process 68- was measured with a densitometer (PD-7).
The color development sensitivity (displayed as a relative value when the sensitivity in the sample αη is set to 100), fog, and maximum density were calculated, and the results were used in the fourth column. Shown in the table.

From the results shown in Table 4, samples α, Hl (14 and H) using the couplers of the present invention have high color development sensitivity with a low silver content compared to samples (+1 and (1m) using the comparative couplers. 69-, it can be seen that it has the highest density and improved coloring performance with low fog.

Comparative coupler (9) (compound described in JP-A-57-17950) Comparative coupler (■) (JP-A-58-20515
Compound described in No. 1) Example 5 The six sample axes prepared in Example 4 were treated with formalin in the same manner as in Example 3, the formalin resistance axis was calculated, and the obtained results are shown in Table 5. show.

Table 5 From the results shown in Table 5, samples a-0I using the coupler of the present invention are samples 0-1 using the comparative coupler.

(Compared to I'h, it can be seen that it is less susceptible to the adverse effects of formalin and has excellent preservation of raw samples.

Patent applicant Konishiroku Photo Industry Co., Ltd.

Claims (1)

[Scope of Claims] A silver halide color photographic light-sensitive material comprising, on a support, at least one photographic constituent layer containing a magenta coupler represented by the following general formula. In the general formula, R1 represents an alkyl group or a cycloalkyl group, R1 represents an alkyl group, an aryl group, or a heterocyclic group, and R1 represents a halogen atom, an alkyl group, an alkoxy group, an alkylthio group, an acylamino group, or an alkoxycarbonyl group. m represents an integer of 0 to 4, n represents an integer of 1 to 2, and Ar represents an aryl group.