JPS6261251B2 - - Google Patents

Description

[Detailed description of the invention]

The present invention relates to a silver halide color photographic light-sensitive material, and more particularly to a novel silver halide color photographic light-sensitive material which has a high maximum color image density and excellent image storage stability. Generally, silver halide photographic materials have high sensitivity and excellent image quality, and have thus far been used for various photographic purposes. However, since silver halide photographic materials require a large amount of silver, the shortage of silver resources and the resulting instability of raw material costs have become a serious problem in recent years, so it is possible to save on the amount of silver. Technology development is required. As one of the techniques to meet this demand, silver-saving silver halide photographic materials have been proposed, and several techniques have already been proposed. For example, Tokko Akira
As described in Japanese Patent Application No. 49-13576, by introducing a substituent into the active site of a color coupler, two atoms of silver were required to form one molecule of dye, whereas conventionally four atoms were required to form one molecule of dye. A technique is known that uses a so-called two-equivalent type coupler in which only 100% of silver is required. According to this method, the amount of silver used can be reduced to half of that when using a conventional so-called 4-equivalent coupler.
It is theoretically possible to reduce the amount of silver to
In recent years, this two-equivalent coupler has been widely used because it can reduce the amount to less than one-fold. On the other hand, after imagewise exposure, a silver halide photographic light-sensitive material containing a color coupler, regardless of whether it is a 2-equivalent type or a 4-equivalent type, is developed with a color developer containing an aromatic primary amine developing agent. Methods of forming dye images are already known. Among the color couplers used, yellow couplers generally have active methylene groups that serve to couple with the oxidation products of aromatic primary amine developing agents to form yellow dyes. The yellow coupler that is most commonly used in practice is of the α-acylacetanilide type, and in particular, the α-pivaloyl-2-chloroacetanilide type yellow coupler, which has a ballast component in its anilide moiety, has other structures. It has excellent storage stability, especially light resistance, compared to yellow couplers with . However, when used as a 4-equivalent type coupler, the color forming property is weak and it is impractical, so a technique for using it as a 2-equivalent type coupler was developed, and it has been put into practical use as an excellent coupler to this day. On the other hand, in terms of development processing, benzyl alcohol has been added to conventional color developing solutions to increase the color development efficiency in photosensitive materials, but benzyl alcohol has problems with environmental pollution, such as BOD.
There are problems such as increasing the (biological oxygen demand) value. Therefore, it is desired to develop a yellow coupler that has sufficient color development even when the amount of benzyl alcohol added is reduced or removed during color development processing. In a color development process in which the amount of benzyl alcohol added is reduced or eliminated, almost all conventionally known α-pivaloylacetanilide type 2-equivalent yellow couplers having a ballast component in the anilide part tend to have poor color development. . In many cases, even a slight change in the amount of high-boiling organic solvent has a large effect on the photographic properties. Among these, only when an alkylsulfamoyl group is introduced into the ballast component of the anilide part, color development is improved, although it cannot be said to be sufficient. However, new drawbacks arise as a result of this, such as an increase in fog density and color staining, and a significant deterioration in image storage stability (particularly light fastness). Therefore, the first object of the present invention is to reduce the amount of benzyl alcohol contained in a color developer (or agent) when developing a silver halide color photographic material to form a dye image. The color development properties were good and sufficient maximum density was obtained even when using high-boiling point solvents, and the photographic properties were not significantly affected by changes in the amount of high-boiling solvent, and stable color development was obtained. It is an object of the present invention to provide a novel yellow coupler with excellent light fastness of dye images. A second object of the present invention is to provide a silver halide color photographic light-sensitive material that uses a novel yellow coupler to form a desirable dye image with high color density and excellent image storage stability. . As a result of various studies, the present inventors have found that an α-acylacetanilide coupler that reacts with the oxidation product of an aromatic primary amine developing agent to produce a yellow image is represented by the following general formula []. The above object could be achieved by using a silver halide color photographic light-sensitive material containing the compound in at least one of the constituent layers of the light-sensitive material. General formula [] (In the formula, A represents a residue obtained by removing one hydrogen atom from a carbon atom other than the active site substitution position of the α-acylacetanilide coupler, R ₁ is an optionally substituted alkyl group, an aryl group, an aralkyl group, a heterocyclic group, an alkyloxy group, an aryloxy group, a heterocyclic group; _R2 represents a hydrogen atom or an optionally substituted alkyl group, an aryl group, an aralkyl group, a heterocyclic group; ₁ and R ₂
may be a group of nonmetallic atoms necessary to form a substituted 5- or 6-membered ring. ) The α-acylacetanilide type coupler according to the present invention can be more preferably represented by the following general formula []. General formula [] (In the formula, R is a substituted or unsubstituted alkyl group, an aliphatic cyclic compound, or an aromatic cyclic compound, particularly preferably a tert-butyl group, a phenyl group, an o-methoxyphenyl group, or a p-methoxyphenyl group. ,Y
is a halogen atom, preferably a chlorine or fluorine atom, or a lower alkoxy group, particularly preferably a methyloxy group. Further, B is a group capable of substituting the benzene nucleus, such as halogen atoms such as chlorine and fluorine, methyl, ethyl, ethoxyethyl, tert-butyl,
Alkyl groups such as dodecyl, methoxy, ethoxy,
Alkoxy groups such as tert-butoxy and ethyloxyethoxy, aryloxy groups such as phenoxy and (3,5-diethoxycarbonyl)phenoxy, alkylthio groups such as ethylthio, hexylthio and benzylthio, arylthio groups such as phenylthio,
These include acylamide groups such as acetamide, benzamide, methanesulfonamide, and benzenesulfonamide, or carboxyl groups. R ₁ is methyl, ethyl, (2,4-di-tertamyl)phenoxymethyl, 1-(m-dodecyloxy)phenoxypropyl-1-yl, 3-(2',4'-di-tertamyl)
-amyl)phenoxypropyl-1-yl, 3-
Alkyl groups such as dodecyloxypropyl-1-yl, phenyl, naphthyl, p-hydroxyphenyl, p-dodecyloxyphenyl, m-carboxyphenyl, p-pivaloylamidophenyl, o
- Phenyl groups such as tetradecyloxyphenyl, m-butoxycarbonylphenyl, p-nitrophenyl, p-cyanophenyl, aralkyl groups such as benzyl, phenethyl, dodecylbenzyl, 2-
Heterocyclic groups such as furanyl and 2-thiophenyl, alkyloxy groups such as dodecyloxy, octadecyloxy, methoxyethyloxy, and dodecylthiopropyloxy, phenoxy, m-chlorophenoxy, 2,4-di-tert-amylphenoxy, p-
Aryloxy groups such as dodecyloxyphenoxy, m-octadecyloxyphenoxy, p-pivaloylamidophenoxy, 2-furanoxy, 2-
It represents a group represented by a heterocyclic oxy group such as thiophenoxy, 2-benzimidazolyloxy, 2-benzoxazolyloxy, etc., and R ₂ is a hydrogen atom or methyl, ethyl, methanesulfonamidoethyl, methanesulfonylethyl, etc. Alkyl group, phenyl, 2,4,6-trichlorophenyl, p-methoxyphenyl, dodecylphenyl,
Octadecylphenyl, m-chlorphenyl, o-
Aryl groups such as hydroxyphenyl, benzyl,
Aralkyl group such as dodecylbenzyl, furan-2
-yl, thiophen-3-yl, imidazoline,
Each represents a group represented by a heterocyclic group such as benzimidazolyl and oxazol-2-yl. Furthermore, R ₁ and R ₂ may be a group of nonmetallic atoms necessary to form a substituted 5- or 6-membered ring. X may be a hydrogen atom or any group that can be eliminated when it undergoes a coupling reaction with the oxidation product of the developing agent, but is preferably bonded via an oxygen atom, nitrogen atom, or sulfur atom. More specifically, it is a group selected from the various groups shown below. (a) -OCOR ₃ (In the formula, R ₃ represents an alkyl group, alkenyl group, phenyl group or terpenyl group which may have a substituent.) (b) -OCOR ₄ (In the formula, R ₄ is a substituted Represents an alkyl group, aryl group, or heterocyclic group that may have a group.) (c) (In the formula, Z ₁ represents a group of nonmetallic atoms necessary to form a saturated or unsaturated 4-, 5-, or 6-membered ring.) (d) (In the formula, Z ₂ represents a group of nonmetallic atoms necessary to form a saturated, unsaturated 4-, 5-, or 6-membered ring.) (e) (In the formula, Z ₃ represents a group of nonmetallic atoms necessary to form a saturated or unsaturated 4-, 5-, or 6-membered ring.) (f) -S-R ₅ (In the formula, R ₅ is represents an alkyl group, alkenyl group, aryl group, or heterocyclic group which may have a substituent.) Typical examples of these groups that can be eliminated during color development are described below. In addition, when the compound represented by the above general formula [] is a bis-type compound, it can preferably be represented by the following general formula []. General formula [] (In the formula, W is two molecules of α at the active point substitution position.
- A divalent linking group necessary for binding an acylacetanilide coupler to form a bis-type coupler. ) Next, representative examples of the above divalent linking group are described below. Next, typical examples of the yellow coupler according to the present invention will be listed, but the present invention is not limited thereto. As is clear from the above specific compound example of the yellow coupler according to the present invention, the coupler used in the present invention has an acylamidosulfonyl group substituted for the benzene nucleus of the anilide part of the α-acylacetanilide coupler. The yellow coupler of the present invention having the above structure has particularly good color development and image quality compared to conventional yellow couplers having a carbonamide group, sulfonamide group, or sulfamoyl group in the benzene nucleus of the acetanilide moiety. It was found that it has extremely excellent properties in terms of storage stability. Such couplers according to the present invention can be easily and economically synthesized by various conventionally known methods. Examples of its synthesis are described below. Synthesis Example 1 [Synthesis of Exemplary Coupler 4] Synthesis of 2-chloro-5-chlorosulfonylnitrobenzene Chlorsulfonic acid was added in a 500 ml three-headed flask.
Add 200 ml, use an oil bath to bring the internal temperature to 30°C, and slowly add 78.5 g of o-chloronitrobenzene. After adding, raise the temperature to 100℃±5
Heat at ℃ for 3 hours. The reaction solution is added to ice water 1. benzene as it produces an oily substance.
The oil was extracted using 500 ml and washed with water. The benzene layer was separated and dried using anhydrous sodium sulfate, and the benzene was distilled off under reduced pressure. Adding 300 ml of n-hexane to the residue yields a white powder. mp58-59℃ Yield 85g. Synthesis of 2-chloro-5-benzylaminosulfonylnitrobenzene In flask 1, add 500 ml of acetonitrile,
25 ml of pyridine, 32 g of benzylamine, 75 g of 2-chloro-5-chlorosulfonylnitrobenzene
Add and boil for 2 hours using an oil bath. When the reaction solution is added to the water in step 2, an oily substance is produced,
Extract with 500 ml of ethyl acetate. The ethyl acetate layer is separated and dried using anhydrous sodium sulfate, and the ethyl acetate is distilled off under reduced pressure. The residue is recrystallized from a mixed solvent of alcohol-n-hexane. 70 g of the target product with a mp of 95 to 97°C was obtained. 2-chloro-5-[N-benzyl-(2,4-
Synthesis of di-tert-amylphenoxy)acetamidosulfonyl]nitrobenzene In flask 1, add 500 ml of acetonitrile,
20 ml of pyridine, 65 g of 2-chloro-5-benzylaminosulfonylnitrobenzene, (2,4-
Add 75 g of di-tert-amylphenoxy)acetyl chloride and boil for 3 hours using an oil bath. Add the reaction solution to water 2 in the same manner as above,
Extract with ethyl acetate. The residue obtained by distilling off the ethyl acetate is treated with activated carbon and crystallized from n-hexane. 58 g of the target product with a mp of 109 to 110°C was obtained. 2-chloro-5-[N-benzyl-(2,4-
Synthesis of di-tert-amylphenoxy)acetamidosulfonyl]aniline. 2-chloro-5-[N-benzyl-(2,4-di-tertamylphenoxy)acetamidosulfonyl]nitrobenzene obtained above
Hydrogenation is carried out by adding 56 g of tetrahydrofuran and 500 ml of Raney-nickel catalyst using 1 marker. The reaction ends when no more hydrogen is absorbed, the Raney-nickel catalyst is filtered off, and the tetrahydrofuran is distilled off under reduced pressure. Obtain 46g of candy. Synthesis of α-pivaloyl-2-chloro-5-[N-benzyl-(2,4-di-tert-amylphenoxy)acetamidosulfonyl]acetanilide. 2-chloro-5-[N-benzyl-(2,4-
40 g of di-tert-amylphenoxy)acetamidosulfonyl]aniline was mixed with 400 ml of xylene and ethyl α-pivaloyl acetate in a three-headed flask.
Add to 15g of the mixture and boil for 1 hour using an oil bath. Thereafter, xylene is slowly distilled off at normal pressure, xylene is added so that the amount of xylene in the container becomes 300 ml, and reaction is carried out for 8 hours. After that, xylene was completely distilled off under reduced pressure, and the residue was purified using column chromatography to obtain a candy-like target product.
Obtained 26g. α-pivaloyl-α-(1-phenyl-2-
benzyl-3,5-dioxo-1,2,4-triazolidin-4-yl)-2-chloro-5-
Synthesis of [N-benzyl-(2,4-di-tert-amylphenoxy)acetamidosulfonyl]anilanilide. α-pivaloyl-2-chloro-5-[N-benzyl-(2,4-di-tert-
amylphenoxy)acetamidosulfonyl]
Dissolve 26 g of acetanilide in 200 ml of chloroform in a 500 ml flask, and dissolve 6 g of sulfuryl chloride in chloroform while stirring at room temperature.
Slowly drop the solution added to 50 ml using a branched separating funnel. After the dropwise addition was completed, the reaction was continued for an additional 30 minutes, and then chloroform was distilled off under reduced pressure. The residue was dissolved in 200 ml of ethyl acetate, and 3 g of anhydrous potassium carbonate and 1-phenyl-2-benzyl-
Add 12 g of 3,5-dioxo-1,2,4-triazolidine and boil for 3 hours using an oil bath.
Add 200 ml of water to the reaction solution and perform extraction. The ethyl acetate layer is separated, washed with water, dried over anhydrous sodium sulfate, and ethyl acetate is distilled off under reduced pressure. The residue was purified using column chromatography to obtain 28 g of the desired exemplified coupler (4) in the form of a candy. The structure is proton-NMR, FD-MASS,
Confirmed using elemental analysis. Elemental analysis value (%) C H N Cl S Calculated value 66.13 6.28 7.28 3.68 3.33 Actual value 65.96 6.19 7.35 3.73 3.25 Synthesis example 2 [Synthesis of exemplary coupler 5] α-pivaloyl-α-(1-phenyl 2-benzyl-3・5-dioxo-1,2,4-triazolidin-4-yl)-2-chloro-5-[N
Synthesis of -ethyl-α-ethyl-α-(3-dodecyloxyphenoxy)acetamidosulfonyl]acetanilide. α-pivaloyl-2-chloro-5-[N-ethyl-N-
{α-(m-dodecyloxy)phenoxy}propion]amidesulfonylacetanilide 35
Put 300g of chloroform into a 500ml flask and add 300ml of chloroform.
ml of sulfuryl chloride, and while stirring at room temperature, add 8 g of sulfuryl chloride to 50 ml of chloroform.
Slowly add the solution added to the solution dropwise using a side-equipped separatory funnel. After the dropwise addition was completed, the reaction was continued for an additional 30 minutes, and then chloroform was distilled off under reduced pressure. Dissolve the residue in 300ml of ethyl acetate and add 4g of anhydrous potassium carbonate.
and 16 g of 1-phenyl-2-benzyl-3,5-dioxo-1,2,4-triazolidine were added and boiled for 3 hours using an oil bath. water in reaction solution
Add 300ml, extract, wash with water, and separate the ethyl acetate layer. The mixture was dried over anhydrous sodium sulfate, ethyl acetate was distilled off under reduced pressure, and the residue was purified using column chromatography to obtain 26 g of the target Exemplary Coupler 5 in the form of a candy. The structure was confirmed using proton-NMR and FD-MASS elemental analysis. Elemental analysis value (%) C H N Cl S Calculated value 64.21 6.84 7.20 3.65 3.30 Actual value 64.09 6.77 7.41 3.71 3.19 When the above coupler according to the present invention is contained in a silver halide photosensitive material, the general Generally, it is used in the range of about 0.07 to 0.7 mol, preferably 0.1 mol to 0.4 mol, but when used as a DIR coupler or for the purpose of improving the properties of other couplers used in combination, Generally about 1 mole of silver halide
It is used in a range of 0.01 to 0.1 mol, preferably about 0.03 to 0.07 mol. When the coupler of the present invention is incorporated into a light-sensitive material, known high-boiling organic solvents such as dibutyl phthalate and ethyl acetate can be used as the coupler solvent. The coupler according to the present invention can be used in various ways depending on the purpose, and exhibits excellent characteristics in each use. The silver halide color photographic light-sensitive material of the present invention can be used, for example, as a silver halide light-sensitive material for a diffusion transfer system, a general negative light-sensitive material, a general reversal light-sensitive material, a general positive light-sensitive material, a direct positive light-sensitive material, and the like. The silver halide used in these various types of silver halide photosensitive materials may be any silver halide such as silver chloride, silver iodide, silver iodobromide, silver chlorobromide, silver chloroiodobromide, etc. These silver halides can be produced by various methods such as a neutral method and an ammonia method depending on the type of light-sensitive material. These silver halides include active gelatin, sulfur sensitizers (such as allylthiocarbamide, thiourea, cystine, etc.)
Selenium sensitizers, reduction sensitizers (e.g. stannous salts,
Chemically sensitized using a noble metal sensitizer (for example, a water-soluble salt of gold, ruthenium, rhodium, indium, etc.) alone or in combination as appropriate. Furthermore, this silver halide can be optically sensitized to a desired wavelength range, such as a zeromethine dye,
Optical sensitization can be carried out using optical sensitizers such as cyanine dyes such as monomethine dyes, dimethine dyes, trimethine dyes, or merocyanine dyes, alone or in combination. As the support for the photosensitive material, known film or sheet materials such as paper, laminated paper, glass, cellulose acetate, polyester, and polycarbonate can be used. The photographic light-sensitive material of the present invention is composed of at least a support and a photosensitive layer provided thereon, but as mentioned above, various layer structures can be adopted depending on the purpose, and generally, It consists of several layers or more. The yellow coupler according to the present invention can be used in appropriate combinations, and can also be used in combination with other two.
Couplers that can be used in combination with the equivalent coupler and the 4-equivalent coupler, each having a different hue of the color-forming dye, are contained in the photosensitive layer for an appropriate photosensitive wavelength range. Further, in the silver halide color photographic light-sensitive material according to the present invention, the photosensitive layer for a certain photosensitive wavelength range may be composed of two or more layers, and furthermore, these photosensitive layers may be used in combinations of different sensitivities. Furthermore, the couplers incorporated in each layer may include couplers that form dyes of the same color but belong to different types, such as a 2-equivalent coupler and a 4-equivalent coupler. This aspect is generally carried out for the purpose of further improving resolution or sensitivity. Furthermore, as described above, the coupler of the present invention can be used in combination with other 2-equivalent type couplers or 4-equivalent type couplers. (a coupler with a split-off group having an azo group as a bonding group), or a so-called DIR coupler (a type of coupler that releases a development inhibitor during color development; for example, a coupler with a split-off group having a thio group as a bonding group at the active site of the coupler) ), etc. In addition, photographic materials may contain various photographic additives in the photosensitive layer and/or other constituent layers (for example, intermediate layer, subbing layer, filter layer, protective layer, image-receiving layer, etc.) depending on the purpose. Examples of such photographic additives include stabilizers, sensitizers, film property improvers, hardeners, spreading agents, coupler solvents, and substantially colorless compounds that release development inhibitors during color development. There are so-called DIR compounds that produce Various photographic additives may be used alone or in combination. On the other hand, the color developing solution for color developing the photosensitive material after exposure has a color developing agent as a main component as described above, but the color developing agent used in the present invention is an aromatic primary amine, and in particular, P-phenylenediamine type products are typical, and specifically, for example, diethyl-P-phenylenediamine hydrochloride, monomethyl-P-phenylenediamine hydrochloride, dimethyl-P-phenylenediamine hydrochloride 2 -Amino-5-diethylaminotoluene hydrochloride 2-amino-5-(N-ethyl-N-dodecylamino)-toluene, N-ethyl-N-β-methanesulfonamidoethyl-3-methyl-4-aminoaniline sulfate salt, N-ethyl-N-β-methanesulfonamidoethyl-4-aminoaniline, 4-
Examples include N-ethyl-N-β-hydroxyethylaminoaniline. These color developing agents may be used alone or in combination of two or more, and if desired, may be used in combination with a black and white developing agent such as hydroquinone.Furthermore, the color developing solution is generally an alkaline agent such as sodium hydroxide, It contains ammonium hydroxide, sodium carbonate, etc., and may further contain various additives, such as an alkali metal halide such as potassium bromide, or a development regulator such as citradinic acid. This color developer is pre-contained in the image-receiving material in some types of diffusion transfer methods, for example, but in such technology, the color developer and the alkaline agent are separated, and only the alkaline agent is used. It is also possible to use a method of containing a color developing agent or a color developing agent, and processing with the other solution at the time of development. The coupler according to the present invention reacts with the oxidation product of the color developing agent produced when silver halide is developed with such a color developer to form a dye, and depending on the type of coupler, may also react with other dyes. form. After color development processing, when silver halide or developed silver in a light-sensitive material is removed from the system, a bleach-fix solution is generally used, but the fixing component is a halogenated solution such as sodium thiosulfate or ammonium thiosulfate. A silver solvent is used, and the bleaching ingredients are red blood salt, ethylenediaminetetra, and diacetic acid.
Iron ammonium or sodium salt is used. The structure of the present invention is as described above, and the coupler capable of reacting with the oxidation product of the aromatic primary amine developing agent according to the present invention is preferably represented by the general formulas [] and []. Due to this special structure, the dye formation speed is fast and there is no fog or fog on the photosensitive layer.
It does not cause color staining, has good dispersibility in constituent layers of photosensitive materials such as photosensitive layers, and can be dispersed at high concentrations. The dye obtained from this coupler is
It has excellent durability against light, heat, and humidity, exhibits sharp absorption without unnecessary light absorption, and has excellent light absorption properties. Furthermore, when the coupler according to the present invention is contained in a silver halide photographic light-sensitive material, the photosensitive layer can be made thinner, and the resolution and sharpness of color images are improved. Since the light transmission properties are improved, the photographic sensitivity is also improved. Furthermore, even if the amount of benzyl alcohol is reduced, there is no need to increase the amount of coupler or silver in the photosensitive layer, and therefore each photosensitive layer can be made thinner, making it suitable for high-temperature and rapid processing. It has various advantages such as being able to obtain silver photosensitive materials. EXAMPLES Hereinafter, the present invention will be explained in more detail with reference to Examples, but the embodiments of the present invention are not limited thereby. Example 1 1.5 x 10 ^-1 mole (per mole of silver halide) of the couplers according to the invention as shown in Table 1 (indicated by the numbers of the exemplary couplers above) and the comparative couplers described below
were heated and dissolved in the same grams of dibutyl phthalate and twice the amount of ethyl acetate, and 5% sodium dodecylbenzenesulfonate was added.
1000 ml of a 5% gelatin solution containing 120 ml was added and emulsified and dispersed using a colloid mill. This dispersion was mixed into a gelatin silver iodobromide emulsion (silver iodide 6
silver halide color photographic material was prepared by coating and drying on a film base. The coating thickness of this sample was 6 μm, and the amount of coated silver was 3.5 g/m ² . These samples were wedge exposed in the usual way,
The following processing was performed. Processing process (38℃) Processing time Color development 3 minutes 15 seconds Bleach 6 minutes 30 seconds Water washing 3 minutes 15 seconds Fixation 6 minutes 30 seconds Water washing 3 minutes 15 seconds Stabilizing bath 1 minute 30 seconds Used in each processing step The composition of the treatment liquid was as follows. [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 and adjust to 1 using potassium hydroxide to pH
Adjust to 10.0. [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 adjust to 1 and use ammonia water to pH
Adjust to 6.0. [Fixer composition] Ammonium thiosulfate (50% aqueous solution) 162 ml Anhydrous sodium sulfite 12.4 g Add water to 1 and adjust the pH to 6.5 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. Development processing was carried out under the above conditions. The results of measuring each density of the obtained color image using a pD-7R densitometer (manufactured by Konishiroku Photo Industry Co., Ltd.) are
Shown in the table. In addition, in order to examine the light fastness and humidity fastness of the obtained color images, after 100 hours of exposure using a xenon fade meter, the images were placed in a constant temperature and humidity chamber at 260°C and 80% relative humidity, and the initial concentration after 2 weeks was measured. The stability of each coupler was investigated using the density after the test at 1.0 as the dye residual rate. As is clear from Table 1, the sample containing the yellow coupler according to the present invention is a yellow coupler having a carbonamide type lipophilic component [Comparative couplers (A) and (B)]
It has particularly excellent color development compared to samples containing
Yellow coupler with sulfonamide or sulfamoyl type lipophilic component [Comparative couplers (C) and (D)]
It is clearly seen that the color development properties and especially the image storage properties are very superior compared to the samples containing . Note that the sensitivity is expressed as a relative sensitivity when sample 1 is taken as 100.

【table】

[Color photographic developer]

Benzyl alcohol 1.0ml Sodium hexametaphosphate 3.00g Anhydrous sodium sulfite 1.85g Sodium bromide 1.40g Potassium bromide 0.50g Boric acid (Na ₂ B ₄ O ₇・10H ₂ O) 39.10 g N-ethyl-N-[2-( Methanesulfonamidoethyl)]-3-methyl-4-aminoaniline sulfate
Add 4.50g water to make up to 1, and add sodium hydroxide.
Adjusted to PH10.3. [White-marking fixer] Ethylenediaminetetraacetate iron ammonium
61.0g 2-ammonium ethylenediaminetetraacetate
5.0g Ammonium thiosulfate 124.5g Sodium metabisulfite 13.3g Sodium sulfite 2.7g Water was added to bring the mixture to 1, and the pH was adjusted to 6.5. [Stabilizing liquid] 20 ml of glacial acetic acid (trihydrate) 800 ml of pure water was added, and the pH was adjusted to 3.5 to 4.0 using sodium acetate trihydrate, and then finished to 1. In order to examine the light fastness of the dye image obtained by developing under the above conditions, each coupler was exposed using a xenon fademeter for 100 hours, and the density after exposure at an initial density of 1.0 was taken as the dye residual rate. Stability was investigated. The dye images of the couplers according to the invention obtained by processing in the above manner are as shown in Table 2, compared to the samples containing comparative couplers (A), (B), (C), and (D), respectively. It can be clearly seen that the color development property when treated with a reduced amount of benzyl alcohol is significantly superior to that of the conventionally widely used carbonamide type yellow coupler, and the light resistance is also very excellent. Note that the sensitivity is expressed as a relative sensitivity when Sample No. 10 is set as 100.

【table】

【table】

【table】

Claims (1)

[Scope of Claims] 1. An α-acylacetanilide coupler that reacts with the oxidation product of an aromatic primary amine developing agent to produce a yellow image is contained in at least one of the constituent layers of the light-sensitive material. A silver halide color photographic light-sensitive material, characterized in that the silver halide color photographic light-sensitive material contains a compound represented by the following general formula [] as the α-acylacetanilide type coupler. General formula [] (In the formula, A represents a residue obtained by removing one hydrogen atom from a carbon atom other than the active site substitution position of the α-acylacetanilide coupler, R ₁ is an optionally substituted alkyl group, an aryl group, Aralkyl group, heterocyclic group, alkyloxy group, aryloxy group, heterocyclicoxy group, _R2 represents a hydrogen atom or an optionally substituted alkyl group, aryl group, aralkyl group, heterocyclic group. ₁ and R ₂
may be a group of nonmetallic atoms necessary to form a substituted 5- or 6-membered ring. )