JPH0426099B2 - - Google Patents

Description

[Detailed description of the invention]

I. BACKGROUND OF THE INVENTION TECHNICAL FIELD The present invention relates to a silver halide color photographic light-sensitive material that exhibits high sensitivity, high color density, and provides magenta dye images with improved storage stability. Prior art and its problems Usually, in silver halide color photographic light-sensitive materials, exposed silver halide grains are reduced with an aromatic primary amine color developing agent, and the color developing agent produced at this time is oxidized. Dye images can be obtained by coupling the body with couplers that form yellow, magenta and cyan dyes. The coupler that has been practically used to form the magenta dye is the pyrazolone type magenta coupler, but this coupler has low maximum color density and sensitivity, has unfavorable side absorption, and has poor storage stability. In particular, it had the disadvantage of poor formalin resistance, resulting in significant changes in color tone and a marked decline in color development. Many proposals have been made in the past to improve these drawbacks. For example, the
No. 30895 includes IH that does not have undesirable side absorptions.
-Pyrazolone[3,2-C]-S-triazole type magenta couplers have been disclosed, but the maximum color density and sensitivity, as well as formalin resistance, have hardly been improved. Further, Japanese Patent Publication No. 16058/1983 discloses a screw type pyrazolone type magenta coupler. Although this coupler shows some improvement in sensitivity and formalin resistance, the maximum color density is insufficient. Furthermore, in JP-A No. 56-135841, IH-
Pyrazolo[3,2-C]-S-triazole type magenta couplers are disclosed. Although this coupler has somewhat improved formalin resistance, maximum color density and sensitivity are inadequate. In addition, JP-A-58-42045 discloses a ballast group containing a hydroxyphenylenesulfonyl group at the end as a ballast group of a coupler for the purpose of improving the maximum color density. However, it is still insufficient. OBJECTS OF THE INVENTION The first object of the present invention is to provide a silver halide color photographic light-sensitive material that exhibits high maximum color density and sensitivity in a magenta color layer and excellent formalin resistance. Second aspect of the present invention
The object of the present invention is to provide a silver halide color photographic material that does not exhibit undesirable side absorption in the magenta coloring layer. A third object of the present invention is to provide a silver halide color photographic light-sensitive material in which a photographic magenta coupler has excellent dispersion stability. A fourth object of the present invention is to provide a silver halide color photographic light-sensitive material that provides excellent dye images using a photographic magenta coupler having these excellent properties. Structure of the Invention The object of the present invention is to provide a silver halide color photographic material having at least one silver halide emulsion layer on a support, in which at least one of the silver halide emulsion layers has the following general formula []. This is achieved by a silver halide color photographic material containing at least one of the magenta couplers shown below. General formula [] [In the formula, R ₁ represents an alkyl group or an aryl group, R ₂ represents a monovalent group, and R ₃ represents an alkylene group, a phenylene group, or at least one alkylene group and at least one phenylene group directly bonded. represents a divalent organic group, R ₄ represents an alkyl group, alkenyl group, aryl group, or heterocyclic group, Z represents a group that can be separated by a coupling reaction with an oxidized color developing agent, and l represents a group from 1 to represents an integer of 5, and m represents an integer of 0 to 4, respectively. ] Detailed Description of the Invention In the above general formula, R ₁ represents an alkyl group or an aryl group, preferably an alkyl group. The alkyl group preferably has 1 to 8 carbon atoms, more preferably 1 to 4 carbon atoms.
Examples of the alkyl group include a methyl group, an ethyl group, an ethoxyethyl group, and a t-butyl group. These alkyl groups may have a substituent. The aryl group represented by R ₁ is preferably
It is a phenyl group, and this phenyl group may have a substituent, such as p-methoxyphenyl group, m-chlorophenyl group, p-(t)-butylphenyl group, etc. R ₂ is a halogen atom (chloro group, etc.), an alkoxy group (methoxy group, t-butoxy group, etc.), an alkyl group (methyl group, ethyl group, methoxyethyl group, benzyl group, etc.), nitro group, cyano group, etc. Represents a valence group. R ₃ represents an alkylene group, a phenylene group, or a divalent organic group in which at least one alkylene group and at least one phenylene group are directly bonded, preferably an alkylene group. The alkylene group preferably has 1 to 20 carbon atoms, such as methylene group, 1,1-ethylene group, 1,3-propylene group, 1,1-dodecylene group, 1,1-tridedylene group, -methyl-2-
Examples include alkylene groups such as ethylene group. The phenylene group represented by R ₃ may have a substituent, and examples thereof include 4-methyl-O-phenylene, 3-chloro-m-phenylene, and 3-methoxy-p-phenylene. Further, examples of the divalent organic group represented by R ₃ in which at least one alkylene group and at least one phenylene group are directly bonded include an alkylenephenylene group, a phenylenealkylene group, an alkylenephenylenealkylene group, and a phenylenealkylene group. Examples include phenylene group. This alkylene group and/or phenylene group may have a substituent. Specifically, the divalent organic group is:

【formula】

【formula】

【formula】

【formula】

[Formula] etc. R ₄ represents an alkyl group, an alkenyl group, an aryl group, or a heterocyclic group, and is preferably an alkyl group or an aryl group. The alkyl group is preferably an alkyl group having 1 to 20 carbon atoms, such as a methyl group, an ethyl group,
Examples include iso-propyl group, n-butyl group, n-hexyl group, cyclohexyl group, n-nonyl group, n-dodecyl group, n-octadecyl group, benzyl group, phenethyl group, and the like. The aryl group is preferably a phenyl group, and the phenyl group may have a substituent. Examples of the substituent include a halogen atom, an alkyl group, an alkoxy group, a carboxy group,
Examples include an alkylamino group, a sulfonamide group, and an alkyloxycarbonyl group. Specifically, m-chlorophenyl group, p-carboxyphenyl group, p-dimethylaminosulfonamidophenyl group, p-tolyl group, 3,5-dimethylphenyl group, p-tert-butylphenyl group, p- n-
dodecylphenyl group, p-methoxyphenyl group,
P-tert-butoxyphenyl group, p-n-dodecyloxyphenyl group, p-n-tetradecyloxyphenyl group, 2-tert-butyl-5-dodecylphenyl group, 2-n-butyloxy-5-tert −
Examples include octylphenyl group, m-dodecyloxycarbonylphenyl group, O-ethoxycarbonylphenyl group, and the like. Examples of the alkenyl group represented by R ₄ include a propenyl group and a butenyl group. Examples of the heterocyclic group represented by R ₄ include a thiazole group, a thiadiazole group, a benzoxazole group, and a tetrazole group, which may have a substituent. Specific examples include thiazol-2-yl group, 5-methylthiadiazol-2-yl group, benzoxazol-2-yl group, and 1-methyltetrazol-5-yl group. The group represented by Z which can be separated by the coupling reaction of the oxidized color developing agent means a group conventionally known as a so-called split-off group of a two-equivalent coupler, and does not contain a hydrogen atom. Specifically, halogen atoms (e.g., chlorine atom, fluorine atom, etc.), aryloxy groups (e.g., phenoxy group, p-methoxyphenoxy group, p-butanesulfonamide phenoxy group, p-tert -butylcarboamidophenoxy group, etc.), arylthio group (e.g., phenylthio group), heterocyclic thio group (e.g., 1-ethyltetrazole-5-thioyl group), etc., but halogen atoms are preferred, particularly preferred. is a chloro atom. l represents an integer from 1 to 5, particularly preferably an integer from 1 to 3. m represents an integer from 0 to 4, particularly preferably 0. In this case, the -NHCOR ₃ SO ₂ R ₄ group in the general formula [] is preferably a ballast group sufficient to impart diffusion resistance to the photographic magenta coupler represented by the general formula. In addition, -NHCOR ₃ SO ₂ R ₄ groups are

[Formula] Although the phenyl group can be bonded to any position relative to the bonding position of the group, it is preferably bonded to the p-position. In addition, in this -NHCOR ₃ SO ₂ R ₄ group, when R ₃ is an alkylene group, R ₄ may be any of an alkyl group, an alkenyl group, an aryl group, or a heterocyclic group, but a substituent is not included. The total number of carbon atoms included is preferably from 8 to 30, particularly preferably from 12 to 25. Also, when R ₃ is phenylene, R ₄
is preferably an alkyl group or a phenyl group, and as a substituent of the phenyl group, an alkyl group,
It is preferably selected from alkoxy groups, alkoxycarbonyl groups, etc., and the number of carbon atoms represented by the alkyl group, alkoxy group, and alkoxycarbonyl group as a substituent of the alkyl group or phenyl group is preferably 8 to 30, Particularly preferably from 8 to 20. Typical specific examples of magenta couplers in the present invention will be described below, but the present invention is not limited thereto.

【table】

【table】

【table】

【table】

【table】

[Table] A typical method for synthesizing the magenta coupler of the present invention is described below. A specific synthesis example of the magenta coupler of the present invention will be described below. Synthesis Example 1 (Synthesis of Exemplary Coupler 3) Dissolve 4.5 g of anhydrous sodium acetate in 150 cc of acetic acid and prepare 6-methyl-3-[3-(P-aminophenyl)-propyl]-IH-pyrazole[3,2] at room temperature. -C]
12.7 g of -S-triazole was added, and then 22.1 g of α-benzylsulfonyltetradecanoyl chloride was added little by little while stirring. After reacting for 5 hours, the reaction solution was added to water to produce an oil. This oil was then extracted using ethyl acetate, washed with water, the oil layer was separated, dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified using silica gel column chromatography and crystallized using ethyl acetate and n-hexane to obtain 16.7 g of white powder. 15.0g of the obtained white powder was added to 150cc of chloroform.
Add to the liquid and dissolve uniformly, then heat to 10℃±5℃ using ice water.
While cooling, a solution of 3.6 g of sulfuryl chloride in 50 cc of chloroform was slowly added dropwise. After dropping the mixture over 1 hour, the reaction was continued for another 1 hour at the same temperature. The reaction solution was added to water, washed with water, and the chloroform layer was separated, dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified using silica gel column chromatography and then recrystallized from acetonitrile. 5.5 g of white powder with a melting point of 75-79°C was obtained. The structure is
Determined using NMR and MASS. Synthesis Example 2 (Synthesis of Exemplary Coupler 9) Dissolve 4.5 g of anhydrous sodium acetate in 150 cc of acetic acid and prepare 6-methyl-3-[3-(p-aminophenyl)-propyl]-IH-pyrazole[3,2] at room temperature. -C]
12.7 g of -S-triazole was added, and then α-(p-dodecyloxyphenylsulfonyl)
23.6 g of butanoyl chloride was added in small portions. After reacting for 5 hours, the reaction solution was added to water to obtain an oily product. This oily product was extracted using ethyl acetate, washed with water, the oil layer was separated, dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified using silica gel column chromatography to obtain an oily substance.
20.0g was obtained. 15.0 g of the obtained oil was added to 150 cc of chloroform and dissolved uniformly, and a solution of 3.4 g of surifuryl chloride in 50 cc of chloroform was added dropwise over 1 hour while cooling the mixture to 10° C.±3° C. using ice water. After further reaction for 1 hour at the same temperature, the reaction solution was added to water, washed with water, the chloroform layer was separated, dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified using silica gel column chromatography to obtain 4.4 g of a colorless caramel. The structure was determined using NMR and MASS. A silver halide color photographic light-sensitive material prepared using the coupler according to the present invention (hereinafter referred to as the coupler of the present invention) may contain a conventionally used dye-forming coupler. As the yellow dye-forming coupler, a known closed ketomethylene coupler can be used. Among these, pivaloylacetanilide couplers or benzoylacetanilide couplers are useful. Specific examples of yellow dye-forming couplers that can be used can be found in U.S. patents.
No. 2875057, UK Patent No. 1077874, US Patent
No. 3408194, Japanese Patent Application Publication No. 1973-123342, Japanese Patent Application Publication No. 1973
-87650, JP 54-133329, JP 46-19031, JP 48-29432, JP 48-66834, JP 48-66835,
JP-A-48-94432, JP-A-50-28834, JP-A-54-99433, JP-A-55-70841, JP-A-56-74249, JP-A-45-19956
No. 51-102636, JP-A-56-
It is described in Publication No. 87041, etc. As the cyan dye-forming coupler, phenol compounds, naphthol compounds, etc. can be used. Specific examples of these compounds include US Patent Nos. 2369929, 2474293, 2772162, and
No. 2895826, British Patent No. 1038331, Special Publication No. 1977-
No. 36894, Japanese Patent Application Publication No. 47-21139, US Patent
No. 3737316, Japanese Unexamined Patent Publication No. 48-74844, US Patent
No. 3880661, No. 4124396, No. 4333999, JP-A-Sho
Publication No. 55-21094, No. 50-112038, No. 50-
Publication No. 117422, Publication No. 52-18315, Publication No. 54-
Publication No. 115230, Publication No. 55-163537, Publication No. 57-
Publication No. 136650, Publication No. 57-155538, Publication No. 57-
Publication No. 204545, Publication No. 55-32071, Publication No. 55-
Publication No. 108662, Publication No. 56-1938, Publication No. 56-27147
Examples include those described in Japanese Patent Publication No. 56-80045, Japanese Publication No. 56-104333, and the like. Furthermore, as the magenta dye-forming coupler, the couplers of the present invention may be used alone or in combination of two or more. Furthermore, conventionally known pyrazolone compounds, indazolone compounds, cyanoacetyl compounds, pyrazolinobenzimidazole compounds, pyrazolotriazole compounds, etc. may be used in combination as appropriate. However, at least one coupler of the invention is used. To use the magenta couplers of the present invention, the methods used for conventional magenta dye-forming couplers are similarly applicable. Typically, a magenta coupler is blended into a silver halide emulsion, and this emulsion is coated on a base to form a silver halide color photographic light-sensitive material. This silver halide color photographic light-sensitive material may be monochromatic or multicolored. In multicolor silver halide color photographic materials, the magenta coupler of the present invention is usually contained in a green-sensitive emulsion, but it may also be contained in a non-sensitized emulsion or an emulsion sensitive to the tertiary dye region of the spectrum other than green. It's okay. Each structural unit forming a dye image in the present invention consists of a single emulsion layer or multiple emulsion layers that are sensitive to a certain region of the spectrum. The layers necessary for the silver halide color photographic light-sensitive material, including the layers of the image-forming structural units described above, can be arranged in various orders as known in the art. A typical multicolor silver halide color photographic light-sensitive material contains a cyan dye image-forming unit consisting of at least one red-sensitive silver halide emulsion containing at least one cyan dye-forming coupler, and at least one magenta dye-forming coupler. a magenta dye image-forming unit consisting of at least one green-sensitive silver halide emulsion layer containing at least one yellow dye-forming coupler, provided that at least one of the magenta dye-forming couplers is a magenta coupler of the present invention; A yellow dye image-forming structural unit consisting of at least one blue-sensitive silver halide emulsion layer is supported on a support. The silver halide color photographic material of the present invention may have additional layers in addition to the above-mentioned layers, such as a filter layer, an intermediate layer, a protective layer, and an undercoat layer. In order to incorporate the magenta coupler according to the present invention and each coupler according to the present invention into a silver halide photosensitive material, a conventionally known method may be followed. For example, the magenta coupler of the present invention or the coupler according to the present invention is dissolved in a mixture of a known high-boiling point solvent and a low-boiling point solvent such as butyl acetate or butyl propionate, and then mixed with an aqueous gelatin solution containing a surfactant. The emulsifier may be emulsified using a high-speed rotary mixer, colloid mill or ultrasonic disperser, and then added to the silver halide emulsion. Known high-boiling point solvents include phthalate esters (e.g. dibutyl phthalate, dioctyl phthalate, etc.), phosphoric acid esters (tricresyl phosphate, trioctyl phosphate, etc.), N
-Substituted acid amides (N,N-diethyllaurinamide, etc.) and the like are included. The silver halide color photographic light-sensitive material according to the present invention contains a phenolic compound (hereinafter referred to as the phenolic compound of the present invention) that is non-color-forming and has diffusion resistance.
It is preferable to use them together. In that case, the phenolic compound of the present invention is preferably contained in the same layer as the silver halide emulsion layer containing the magenta coupler of the present invention. The phenolic compound of the present invention is non-chromic,
Preferably, it should be a diffusion-resistant solvent, and for example, conventionally known phenolic high-boiling organic solvents used for coupler dispersion can be used. In the present invention, the phenolic compound of the present invention includes a phenolic compound that has a melting point of 50°C or less and is solid at room temperature (25°C), or a phenolic compound that is liquid at room temperature and has a boiling point higher than 200°C at normal pressure (1 atm). is included. Furthermore, the phenolic compound of the present invention preferably has a group for imparting diffusion resistance. The phenolic compound of the present invention preferably has
It is a phenol compound represented by the following general formula []. General formula []

[Color developer composition]

4-amino-3-methyl-N-ethyl-N-
(β-hydroxyethyl)-aniline sulfate
4.75g Anhydrous sodium sulfite 4.25g Hydroxyamine 1/2 sulfate 2.0g Anhydrous potassium carbonate 37.5g Sodium bromide 1.3g Nitrilotriacetic acid trisodium salt (monohydrate)
2.5g Potassium hydroxide 1.0g Add water to make 1, and use potassium hydroxide to
Adjust to PH10.0. [Bleach solution composition] Ethylenediaminetetraacetic acid iron ammonium salt
100.0g Ethylenediaminetetraacetic acid diammonium salt
10.0g Ammonium bromide 150.0g Glacial acetic acid 10.0ml Add water to make 1, and adjust the pH using ammonia water.
Adjust to 6.0. [Fixer composition] Ammonium thiosulfate (50% aqueous solution) 162ml Anhydrous sodium sulfite 12.4g Add water to make 1, and adjust to PH6.5 using acetic acid. [Stabilizing liquid composition] Formalin (37% aqueous solution) 5.0ml Konidax (manufactured by Konishiroku Photo Industry Co., Ltd.)
Add 7.5ml water to make 1.

[Table] Color density of formalin-untreated samples
As shown in Table 1, comparative coupler 1 has a structure similar to the coupler of the present invention and shows good results in terms of sensitivity, maximum concentration, and formalin resistance, but to the extent desired by the inventors. However, it was still insufficient. Comparative coupler 2 has a structure more similar to the coupler of the present invention than comparative coupler 1, and is a coupler in which the 6th position of the pyrazolotriazole core is hydrogen, but it has extremely high specific sensitivity, maximum concentration, and formalin resistance. It was at a low level. Comparative coupler 3 is a compound in which the 1st position of comparative coupler 2 is substituted with the active site of a compound having an active methylene group, and is a compound with improved formalin resistance. However, although a slight improvement was observed in the specific sensitivity and maximum density of Comparative Coupler 3, both were at low levels, and although an improvement was observed in formalin resistance, it was still insufficient.
Comparative coupler 4 is a compound in which the 6th position of comparative coupler 3 is replaced with a chlorine atom, and is a compound with improved specific sensitivity, maximum concentration, and formalin resistance.
Both were still insufficient. In contrast, Samples 5, 6 and 7 containing the magenta coupler of the present invention were fully satisfactory in terms of specific sensitivity, maximum concentration and formalin resistance. The results in Table 1 show that in Comparative Couplers 2, 3, and 4, which have the same group as the diffusion-resistant group of the present invention, in order to satisfy all of the sensitivity, maximum concentration, and formalin resistance, it is necessary to use the pyrazolotriazole matrix. It is necessary that the 1st position of the nucleus is hydrogen, and that the 6th position is substituted with a group capable of coupling with the oxidized product of the color developing agent, such as a chlorine atom. Furthermore, although Comparative Coupler 1 satisfied the above-mentioned requirements, the results obtained were still unsatisfactory. It is understood from this that the effects of the present invention are completely surprising. Example 2 A magenta coupler of the present invention and a comparative coupler were prepared in the same manner as in Example 1, and Samples 8 to 14 were prepared and processed in the same manner as in Example 1. The results are shown in Table 2.

【table】

As shown in Table 2, comparative coupler 5 is:
Although it is a coupler that has been in practical use for a long time,
This coupler has low sensitivity and maximum density, and also has poor storage stability, especially formalin resistance. Comparative coupler 6 had improved sensitivity but poor maximum density and formalin resistance. Comparative coupler 7 showed improvement in maximum density and formalin resistance, but was still insufficient in sensitivity. Comparative coupler 8 is a coupler developed by the present inventors, and although it shows improvements in sensitivity, maximum density, and formalin resistance, it is not satisfactory to the present inventors. As shown in Table 2, the magenta coupler of the present invention was superior to both the conventionally known magenta coupler and Comparative Coupler 8 in sensitivity and maximum density, and also exhibited high formalin resistance. It will be appreciated that the effects of the present invention are also completely unexpected and surprising. As shown in Examples 1 and 2, the magenta coupler of the present invention is a material that exhibits high sensitivity and high color density, and also exhibits stable color development even when stored, especially in the presence of formalin. Therefore, by a conventionally known method, an open-chain active methylene yellow coupler was added to a blue-sensitive silver halide emulsion, the magenta coupler of the present invention was added to a green-sensitive silver halide emulsion, and a phenol or naphthol-based cyan coupler was added to the blue-sensitive silver halide emulsion. By adding each of these to a red-sensitive silver halide emulsion and further using various additives as appropriate and coating them on a transparent support, we succeeded in obtaining a completely new silver halide color photographic light-sensitive material with stable color balance. Example 3 0.1 mol of each of the magenta couplers of the present invention shown in Table 3 and the following comparative couplers were taken per 1 mol of silver, and the same weight of tricresyl phosphate and the phenolic compound of the present invention as the couplers were added. An appropriate amount of ethyl acetate was added to the coupler in an amount three times the weight of the coupler, and the mixture was heated to 60°C to completely dissolve the coupler. This solution was mixed with a 5% aqueous solution of Alkanol B (alkylnaphthalene sulfonate, manufactured by Dupont).
Mix with 1200ml of 5% gelatin aqueous solution containing 120ml,
An emulsion was obtained by emulsification and dispersion using an ultrasonic dispersion liquid. Thereafter, this dispersion was added to 4 kg of green-sensitive silver iodobromide emulsion (containing 5 mol% silver iodide), and a 2% solution of 1,2-bis(vinylsulfonyl)ethane (water: methanol) was added as a hardener. = 1:1) was added, coated on a subbed transparent polyester base, and dried to prepare samples 15 to 37. (Amount of silver coated
20 mg/100 cm ² ) The sample thus obtained was subjected to wedge exposure according to a conventional method and then developed. Table 3 shows the results. The processing steps, color developing solution composition, bleaching solution composition, fixing solution composition, and stabilizing solution composition were the same as in Example 1.

[Table] Comparative couplers 5, 6, 7 and 8 are the same as those described in Example 2. As is clear from Table 3, although Comparative Coupler 5 is a coupler that has been used in practical use, it showed poor results in terms of sensitivity, maximum density, and formalin resistance. Furthermore, some improvement can be seen even when used together with the phenolic compound of the present invention, but it is not to the extent expected by the present inventors. On the other hand, comparative coupler 6 has improved sensitivity, but the maximum color density and
Both formalin resistance values are low, and even when the phenol compound of the present invention is added, little effect is observed. Comparative coupler 7 showed significant improvements in maximum color density and formalin resistance, but had low sensitivity and little effect even when used in combination with the phenolic compound of the present invention. Furthermore, Comparative Coupler 8 showed improvements in sensitivity, maximum color density, and formalin resistance, but was ultimately insufficient to the extent expected by the inventors. On the other hand, the magenta coupler of the present invention has performance equivalent to or higher than the maximum color density and formalin resistance shown by Comparative Couplers 7 and 8 by appropriately using the phenolic compound of the present invention, and We have successfully developed a silver halide color photographic material that has significantly improved sensitivity and also forms a magenta dye with good spectral absorption characteristics. Example 4 0.1 mol of each of the magenta couplers of the present invention as shown in Table 4 was taken per 1 mol of silver, and 2,4-di-tert-amylphenol of the same weight as the coupler and 3 times the weight of the coupler were added. of ethyl acetate was added and heated to 60°C to completely dissolve. This solution was mixed with 1200 ml of a 5% aqueous gelatin solution containing 120 ml of a 5% aqueous solution of Alkanol B (alkylnaphthalene sulfonate, manufactured by Dupont) and emulsified and dispersed using an ultrasonic disperser to obtain an emulsion. after that,
This dispersion was added to 4 kg of green-sensitive silver iodobromide emulsion (containing 5 mol% silver iodide), and a 2% solution of 1,2-bis(vinylsulfonyl)ethane (water:
120 ml of methanol (1:1) was added, coated and dried on a subbed transparent polyester base, and the coated silver amount was adjusted to 10 mg/100 cm ² . For comparison, sample 15 used in Example 3,
17, 21, and 19 were used. The sample thus obtained was subjected to wedge exposure according to a conventional method, and then developed in the same manner as in Example 3.

【table】

[Table] Represents each lufenol.
As shown in Table 4, the system using the coupler of the present invention and the phenolic compound of the present invention has sensitivity and maximum color development equivalent to or higher than that of the comparative coupler, despite having half the amount of silver. It shows the concentration. This suggests that the combination of the coupler of the present invention and the phenolic compound of the present invention has high utilization efficiency for silver halide, and it is possible to reduce the amount of silver and thereby thin the film and apply it to other layers. It is understood that this material can fully satisfy the objectives of the present invention, such as improved sharpness. As shown in Examples 3 and 4, the combined use of the magenta coupler of the present invention and the phenolic compound of the present invention provides high sensitivity and
Because it exhibits high color density and stable color development even when stored, especially in the presence of formalin, the closed-active methylene yellow coupler was blue-sensitive halogenated using a conventionally known method. The magenta coupler and phenolic compound of the present invention are added to a green-sensitive silver halide emulsion, and the phenol or naphthol-based cyan coupler is added to a red-sensitive silver halide emulsion to a silver emulsion, and various additives are used as appropriate to transfer them onto a transparent support. Through coating, we succeeded in obtaining a completely new silver halide color photographic material with stable color balance.

Claims (1)

[Scope of Claims] 1. A silver halide color photographic light-sensitive material having at least one silver halide emulsion layer on a support, wherein at least one of the silver halide emulsion layers contains a magenta compound represented by the following general formula []. A silver halide color photographic material containing at least one coupler. General formula [I] [In the formula, R ₁ represents an alkyl group or an aryl group, R ₂ represents a monovalent group, and R ₃ represents an alkylene group, a phenylene group, or 2 in which at least one alkylene group and at least one phenylene group are directly bonded. represents a valent group, R ₄ is an alkyl group,
represents an alkenyl group, an aryl group, or a heterocyclic group, Z represents a group that can be separated by a coupling reaction with a conjugated color developing agent, l represents an integer from 1 to 5, and m represents an integer from 0 to 4. respectively. ]