JP3289177B2 - New photographic coupler and silver halide color photographic light-sensitive material - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a photographic coupler used as a material for a silver halide color photographic light-sensitive material, and more particularly to a novel photographic coupler capable of forming a dye image having excellent fastness to heat, humidity and light. The present invention relates to a coupler for use.

[0002]

2. Description of the Related Art Conventionally, when a color photographic image material is generally obtained, a silver halide color photographic light-sensitive material (hereinafter, also simply referred to as a light-sensitive material) is exposed to light and then subjected to color development processing to obtain an exposed area. In the above, the oxidized aromatic primary amine color developing agent reacts with the dye-forming coupler to form a dye, and a color image is formed.In such a photographic method, a color reproduction method by a subtractive color method is used. Used
Thereby, yellow, magenta and cyan color images are formed.

Conventionally, photographic couplers used for forming the yellow image include, for example, acylacetanilide couplers, and magenta image forming couplers include, for example, pyrazolone and pyrazolobenzimidazole. Pyrazolotriazole or indazolone couplers are known, and as a coupler for cyan image formation, for example, phenol or naphthol couplers are generally used,
It is desired that the dye images obtained from these couplers do not discolor even if exposed to light for a long time or stored under high temperature and high humidity.

However, as a yellow image forming coupler, it has hitherto been widely used and studied.
Dyes formed from benzoylacetanilide-based and pivaloylacetanilide-based couplers are remarkably decomposed under high humidity, which is probably due to hydrolysis, and are not sufficiently fast to light. Examples of yellow couplers satisfying good color reproducibility and high color development and further improving light resistance are disclosed in, for example,
Yellow couplers having an alkoxy group at the 2-position of the anilide moiety and an acylamino group at the 5-position as described in No. 123047 can be mentioned. However, these couplers have inherently high pKa and are not at a completely satisfactory level in terms of color development. JP-B-49-17734,
JP-A-50-130442 and JP-A-50-139736
No. 61-115157, West German Patent 1,956,2
No. 81, JP-A-4-218042 and Research Disclosure 15737 describe acylacetamide type yellow couplers having a group in which the acyl moiety is substituted with a hetero atom. It is clear that the dyes obtained from these couplers are not at a satisfactory level in terms of light resistance, heat resistance and moisture resistance.

[0005]

Accordingly, in view of the above problems, a first object of the present invention is to provide a photographic coupler used as a material for a silver halide color photographic light-sensitive material. A second object is to provide a photographic coupler capable of forming a color image without discoloration due to heat, moisture and light. Another object of the present invention is to provide a silver halide color photographic light-sensitive material which forms a color image without discoloration caused by heat, moisture and light.

[0006]

The above object of the present invention is achieved by the following constitution.

1) A photographic coupler represented by the general formula [I].

[0008]

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In the formula, R and R ₁ represent a substituent, and m represents 0 or an integer of 1-3. When m is an integer of 2 or more, a plurality of Rs may be the same or different. X
Represents a hydrogen atom or a group which is released by a reaction with an oxidized form of a color developing agent.

2) A photographic coupler represented by the general formula [II].

[0011]

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In the formula, R 'and R ₁ ' represent a substituent;
m 'represents 0 or an integer of 1 to 3. When m 'is an integer of 2 or more, a plurality of R's may be the same or different. X 'represents a group which is released by a reaction with an oxidized form of the color developing agent.

3) A silver halide color photographic light-sensitive material having a silver halide emulsion layer containing at least one photographic coupler represented by the general formula [I] or [II].

Hereinafter, the present invention will be described more specifically. In the general formulas (I) and (II), the substituents represented by R, R ₁ , R ′ and R ₁ ′ are not particularly limited, but are typically aliphatic, aryl, anilino, acylamino, sulfone Examples include amide, alkylthio, arylthio, alkenyl, and cycloalkyl groups.In addition to these, a halogen atom and cycloalkenyl, alkynyl, heterocycle, sulfonyl, sulfinyl, phosphonyl,
Acyl, carbamoyl, sulfamoyl, cyano, alkoxy, heterocyclic oxy, siloxy, acyloxy, carbamoyloxy, amino, imide, ureido, sulfamoylamino, alkoxycarbonylamino, aryloxycarbonylamino, alkoxycarbonyl, aryloxycarbonyl, hydroxy, Examples include groups such as carboxy and heterocyclic thio, as well as spiro compound residues and bridged hydrocarbon compound residues.

Hereinafter, the present invention will be described in more detail. R,
The aliphatic groups represented by R ₁ , R ′ and R ₁ ′ may be linear or branched, and may be saturated or unsaturated. The aliphatic group may be substituted with another substituent, and the substituent is not particularly limited, but typically, aryl, anilino, acylamino, sulfonamide, alkylthio, arylthio, alkenyl, cycloalkyl Examples of each group include alkyl and the like.In addition, halogen atoms and cycloalkenyl, alkynyl, heterocycle, sulfonyl, sulfinyl, phosphonyl, acyl, carbamoyl, sulfamoyl, cyano, alkoxy, heterocycle oxy, siloxy, acyloxy, carbamoyloxy , Amino, alkylamino, imide, ureido, sulfamoylamino, alkoxycarbonylamino, aryloxycarbonylamino, alkoxycarbonyl, aryloxycarbonyl, hydroxy, carboxy, heterocyclic thio and other groups, A spiro compound residue Rabbi, bridged hydrocarbon compound residue and the like are also mentioned.

As the aryl group, a phenyl group, a 1-naphthyl group and a 2-naphthyl group are preferred.

Examples of the acylamino group include an alkylcarbonylamino group and an arylcarbonylamino group.

Examples of the sulfonamide group include an alkylsulfonylamino group and an arylsulfonylamino group.

Examples of the alkyl component and the aryl component in the alkylthio group and the arylthio group include linear and branched alkyl groups, phenyl groups, 1-naphthyl groups and 2-naphthyl groups, which are further substituted by other substituents. It may be.

The alkenyl group may have 2 to 3 carbon atoms.
2, the cycloalkyl group has 3 to 3 carbon atoms.
12, preferably 5 to 7, and the alkenyl group may be linear or branched.

The cycloalkenyl group is preferably one having 3 to 12 carbon atoms, particularly preferably 5 to 7 carbon atoms.

Examples of the sulfonyl group include an alkylsulfonyl group and an arylsulfonyl group. Examples of the sulfinyl group include an alkylsulfinyl group and an arylsulfinyl group. Examples of the phosphonyl group include an alkylphosphonyl group, an alkoxyphosphonyl group and an aryloxyphosphonyl group. Group,
Arylphosphonyl group, etc .; acyl group, alkylcarbonyl group, arylcarbonyl group, etc .; carbamoyl group, alkylcarbamoyl group, arylcarbamoyl group, etc .; sulfamoyl group, alkylsulfamoyl group, arylsulfamoyl group An acyloxy group such as an alkylcarbonyloxy group or an arylcarbonyloxy group; a carbamoyloxy group such as an alkylcarbamoyloxy group or an arylcarbamoyloxy group; a ureido group such as an alkylureido group or an arylureido group; Examples of the famoylamino group include an alkylsulfamoylamino group, an arylsulfamoylamino group, and the like;
2-membered groups are preferred, specifically, 2-furyl group, 2-thienyl group, 2-pyrimidyl group, 2-benzothiazolyl group and the like; As the heterocyclic oxy group, a 5- to 7-membered heterocyclic oxy group is preferred, 3,4,5,6-tetrahydropyranyl-2-oxy group, 1-phenyltetrazol-5-oxy group and the like; As the heterocyclic thio group, a 5- to 7-membered heterocyclic thio group is preferable. Pyridylthio group, 2-benzothiazolylthio group, 2,4-diphenoxy-1,3,5
-Triazine-6-thio group and the like; siloxy group as trimethylsiloxy group, triethylsiloxy group, dimethylbutylsiloxy group and the like; imide group as succinimide group, 3-heptadecylsuccinimide group, phthalimide group and glutar Imido group and the like; spiro compound residues such as spiro [3.3] heptane-1-yl and the like; bridged hydrocarbon compound residues as bicyclo [2.2.1] heptane-1-yl and tricyclo [ 3.3.1.1 ^37] decane-1-yl, 7,7-dimethyl - bicyclo [2.2.
1] Heptan-1-yl and the like.

R and R 'are preferably aliphatic,
Aryl, acylamino, sulfonamide, halogen atom, acyl, carbamoyl, sulfamoyl, alkoxy, acyloxy, carbamoyloxy, imide, ureido, sulfamoylamino, alkoxycarbonylamino, aryloxycarbonylamino, alkoxycarbonyl, aryloxycarbonyl, hydroxy Each group is mentioned.

More preferably, R ₁ and R ₁ 'are an aliphatic group, an aryl group, an aliphatic oxy group, an acylamino group, an imide group, a sulfonamide group, a sulfamoylamino group, an oxycarbonylamino group and a phosphonylamino. Each group of the group is mentioned.

Examples of the group capable of leaving by reacting with the oxidized form of the color developing agent represented by X and X 'include, for example, a halogen atom (a chlorine atom, a bromine atom, a bromine atom, etc.), alkoxy, aryloxy, hetero Ring oxy, acyloxy, sulfonyloxy, alkoxycarbonyloxy, aryloxycarbonyloxy, alkyloxalyloxy, alkoxyoxalyloxy, alkylthio, arylthio, heterocyclic thio, alkoxythiocarbonylthio, acylamino, sulfonamide, bonded with N atom Examples of the group include a nitrogen-containing heterocyclic ring, alkyloxycarbonylamino, aryloxycarbonylamino, and carboxyl, and preferably a halogen atom, particularly a chlorine atom, and alkoxy, aryloxy, alkylthio, and arylthio groups. .

Hereinafter, typical specific examples of the coupler of the present invention are shown, but the present invention is not limited thereto.

[0027]

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[0028]

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[0029]

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Next, a synthesis example of the compound represented by the general formula [I] will be shown.

[0031]

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Synthesis Example Synthesis of Exemplified Compound (I-3) (1) Synthesis of Intermediate-1 and Intermediate-2 25 g of pentadecylacetoimidate.HCl and 9.
After stirring 6 g of 3-aminoindazole in 1.2 l of chloroform at room temperature for 18 hours, the chloroform was distilled off to obtain Intermediate-1. The intermediate-1 was immediately dissolved in 800 ml of methanol without purification, 6.9 g of hydroxylamine.HCl and water saturated with 16.4 g of sodium acetate were added, and the mixture was stirred at room temperature for 0.5 hour. . After heating under reflux for another 2 hours, methanol was distilled off, and the residue was thoroughly washed with water.
Recrystallization from 0 gave 21 g of Intermediate-2 (88% yield). Melting point 95 [deg.] C. The structure of Intermediate-2 is represented by NMR, IR,
And mass spectra.

(2) Synthesis of Intermediate-3 9.5 g of p-toluenesulfonic acid chloride was added to 9.5 g of p-toluenesulfonic acid chloride at room temperature in 300 ml of ethyl acetate containing 5 ml of pyridine.
After 9.5 g of Intermediate-2 was suspended and stirred for 2 hours, the reaction solution was filtered and the solvent was distilled off without heating the filtrate to obtain Intermediate-3 in an unpurified state.

(3) Synthesis of Exemplified Compound (I-3) 600 ml of methanol containing 5 ml of pyridine was added to the above intermediate 3 in the unpurified state, and the mixture was allowed to stand at room temperature overnight and then heated under reflux for 3 hours. After that, methanol was distilled off.
A solid obtained by adding 150 ml of water and 150 ml of methylene chloride to the residue was collected by filtration, and recrystallized from ethanol to give 12 g of Exemplified Compound (I-3) (63% yield).
Obtained. Melting point 181 [deg.] C. The structure of the exemplary compound (I-3) is
Confirmed by NMR, IR, and mass spectrum. Exemplified compounds other than Exemplified Compound I-3 were also synthesized according to the above Synthesis Examples, starting from the corresponding raw materials. The coupler of the present invention is generally used in an amount of 1 per mol of silver halide.
× 10 ^-3 to 1 mol, preferably 1 × 10 ^-2 to 8 × 10 ^-1
It can be used in the molar range. Further, the photographic coupler of the present invention mainly shows yellow coloration. Therefore, it can be used in combination with other types of yellow couplers. The yellow coupler of the present invention can be used alone or in combination of two or more. Further, it can be used in combination with any known pivaloylacetanilide, benzoylacetanilide or malondiamide yellow coupler.

The methods and techniques used in conventional dye-forming couplers are similarly applied to the couplers of the present invention.

The photographic coupler of the present invention can be used as a material for forming a color photograph by any coloring method, and specific examples thereof include an external coloring method and an internal coloring method. When used as an external color developing method, the coupler of the present invention can be used by dissolving it in an aqueous alkali solution or an organic solvent (eg, alcohol) and adding it to a developing solution.

When the photographic coupler of the present invention is used as a material for forming a color photographic image by an internal color developing method, the photographic coupler of the present invention is contained in a photographic light-sensitive material.

Typically, a method of forming a silver halide color photographic light-sensitive material by incorporating the photographic coupler of the present invention into a silver halide emulsion and coating the emulsion on a support is preferably used. The photographic coupler of the present invention is used for silver halide color photographic light-sensitive materials such as negative and positive films and color printing paper.

The light-sensitive material using the photographic coupler of the present invention such as the color photographic paper may be of a single color or a multicolor. In a multicolor light-sensitive material, the coupler of the present invention may be contained in any layer, but is usually contained in a blue-sensitive silver halide emulsion layer. The multicolor light-sensitive material has a dye image-forming constituent unit having photosensitivity in each of three primary color regions of the spectrum. Each structural unit can be composed of a single layer or multiple emulsion layers sensitive to certain regions of the spectrum. The constituent layers of the light-sensitive material, including the layers of the image forming constituent units, can be arranged in various orders as known in the art. A typical multicolor light-sensitive material comprises a cyan dye image-forming unit comprising at least one red-sensitive silver halide emulsion layer containing at least one cyan coupler, and at least one green containing at least one magenta coupler. Magenta dye image-forming constitutional unit comprising a light-sensitive silver halide emulsion layer, and yellow dye image-forming constitutional unit comprising at least one blue-sensitive silver halide emulsion layer containing at least one yellow coupler (at least one yellow coupler) Is the yellow coupler of the present invention) on a support.

The light-sensitive material used in the present invention may have additional layers such as a filter layer, an intermediate layer, a protective layer, an undercoat layer and the like. The photographic coupler of the present invention can be incorporated into an emulsion by a conventionally known method. For example, the coupler of the present invention may be added to a high-boiling organic solvent having a boiling point of 175 ° C. or more, such as tricresyl phosphate or dibutyl phthalate, or a low-boiling solvent such as butyl acetate or butyl propionate alone or, if necessary, a mixture thereof. Is dissolved alone or in combination, then mixed with a gelatin aqueous solution containing a surfactant, and then emulsified by a high-speed rotary mixer or a colloid mill, and then added to silver halide to be used in the present invention. A silver emulsion can be prepared.

The silver halide composition preferably used in the photographic material using the photographic coupler of the present invention includes silver chloride, silver chlorobromide or silver chloroiodobromide. Further, a combination mixture such as a mixture of silver chloride and silver bromide may be used.
That is, when a silver halide emulsion is used for color printing paper, particularly fast developability is required. Therefore, the silver halide composition of the silver halide preferably contains a chlorine atom, and at least 1% of silver chloride. Is preferably silver chloride, silver chlorobromide or silver chloroiodobromide.

The silver halide emulsion is chemically sensitized by a conventional method. Also, it can be optically sensitized to a desired wavelength range. Silver halide emulsions are known as antifoggants or stabilizers in the photographic industry for the purpose of preventing fog during the production process, storage, or photographic processing of light-sensitive materials, and / or maintaining stable photographic performance. Can be added.

The silver halide color photographic light-sensitive material using the photographic coupler of the present invention includes a color fogging inhibitor, a dye image stabilizer, an ultraviolet absorber, which are usually used in light-sensitive materials.
An antistatic agent, a matting agent, a surfactant and the like can be used. These are discussed, for example, in Research Disclosure,
176, pages 22 to 31 (December 1978) can be referred to.

The silver halide color photographic material using the photographic coupler of the present invention can form an image by performing a color development process known in the art.

The silver halide color photographic light-sensitive material using the photographic coupler of the present invention contains a color developing agent in the hydrophilic colloid layer as the color developing agent itself or as a precursor thereof, and is provided with an alkaline activating bath. It can also be processed.

The silver halide color photographic light-sensitive material using the photographic coupler of the present invention is subjected to bleaching and fixing after color development. The bleaching process may be performed simultaneously with the fixing process.

After the fixing process, a washing process is usually performed. Further, a stabilization treatment may be performed as an alternative to the water washing treatment, or both may be used in combination.

[0048]

EXAMPLES The present invention will be described in detail below with reference to examples, but embodiments of the present invention are not limited thereto.

Example 1 The following layers were sequentially coated on a paper support laminated on both sides with polyethylene from the support side, and a blue-sensitive color light-sensitive material sample 1 was prepared. In the following examples, the amount of the compound added is represented per 1 m ² unless otherwise specified (silver halide is a silver equivalent value).

First layer: emulsion layer 2.4 g of gelatin, blue-sensitive silver chlorobromide emulsion (silver chloride 99.
The following coupler (a) 17.4 × dissolved in 0.5 g of 0.5 g of dioctyl phthalate) and 1.0 g of dioctyl phthalate
A blue-sensitive emulsion layer consisting of 10 ^-4 mol.

[0051]

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Second layer: protective layer A protective layer containing 0.50 g of gelatin. In addition, 2,4-dichloro-6-hydroxy-s-triazine sodium salt was added as a hardening agent so as to be 0.017 g per 1 g of gelatin.

Next, except that the comparative coupler (a) used in the sample 1 was replaced with the photographic coupler according to the present invention (the amount added was the same molar amount as the comparative coupler (a)) shown below, Samples 2 to 8 of the present invention were prepared.

Each sample contains a hardener, an activator, an antifungal agent (2-
Methylisothiazol-3-one and 5-chloro-2-
A mixture of methylisothiazol-3-one) was added.

Each of the samples 1 to 8 obtained above was subjected to wedge exposure according to a conventional method, and then subjected to development processing in the next step.

The processing conditions are as follows.

Processing Step Temperature Time Color Development 35.0 ± 0.3 ° C. 45 seconds Bleaching Fix 35.0 ± 0.5 ° C. 45 seconds Stabilization 30-34 ° C. 90 seconds Drying 60-80 ° C. 60 seconds [Color developing solution] Pure water 800 ml Triethanolamine 10 g N, N-diethylhydroxylamine 5.0 g Potassium bromide 0.02 g Potassium chloride 2.0 g Potassium sulfite 0.3 g 1-hydroxyethylidene-1,1-diphosphonic acid 1 1.0 g Ethylenediaminetetraacetic acid 1.0 g Catechol-3,5-diphosphonic acid disodium 1.0 g Diethylene glycol 10 g N-ethyl-N-β-methanesulfonamidoethyl-3-methyl-4-aminoaniline sulfate 4.5 g Fluorescent whitening agent (4,4'-diaminostilbene disulfonic acid derivative) 1.0 g Potassium carbonate The total volume of 1l was added to 7g water, adjusted to PH10.10.

[Bleaching and Fixing Solution] Ethylenediaminetetraacetic acid ferric ammonium dihydrate 60 g Ethylenediaminetetraacetic acid 3.0 g Ammonium thiosulfate (70% solution) 100 ml Ammonium sulfite (40% solution) 27.5 ml And adjust the pH to 5.7 with potassium carbonate or glacial acetic acid.

[Stabilizing Solution] 5-chloro-2-methyl-4-isothiazolin-3-one 0.2 g 1,2-benzisothiazolin-3-one 0.3 g ethylene glycol 1.0 g 1-hydroxyethylidene- 1,1-diphosphonic acid 2.0 g O-phenylphenol sodium 1.0 g ethylenediaminetetraacetic acid 1.0 g ammonium hydroxide (20% aqueous solution) 3.0 g fluorescent brightener (4,4'-diaminostilbene disulfonic acid derivative) Add 1.5 g water to make the total volume 1 liter, and adjust the pH to 7.0 with sulfuric acid or potassium hydroxide.

The density of each of the samples 1 to 8 thus treated was measured using a densitometer (model KD-7, manufactured by Konica Corporation).
(C, 60% RH) atmosphere for 20 days to examine the heat resistance and moisture resistance of the dye image. The results are shown below. Here, the heat resistance / moisture resistance is represented by the percentage of the dye remaining after the heat resistance / humidity test with respect to the initial concentration of 1.0. Further, each sample was exposed to sunlight for 4 weeks, and the light fastness of the dye image was examined from the dye remaining rate after the light fastness test at an initial density of 1.0.

Dye Residual Rate (%) Sample No. Coupler used Heat / moisture resistance / light resistance 1 Comparison (a) 84 78 2 Invention (I-3) 91 85 3 Invention (I-4) 90 884 Invention (I-5) 92 895 Invention ( I-6) 87 91 6 The present invention (I-7) 88 90 7 The present invention (II-1) 89 878 The present invention (II-2) 9288 As is clear from the above results, the coupler of the present invention is Compared to the sample using the comparative coupler, the sample used had significantly improved light fastness and excellent heat and humidity resistance, indicating that a robust dye image was formed.

Example 2 On a subbed triacetyl cellulose film support, the following layers were sequentially coated from the support side, and a blue-sensitive color reversal light-sensitive material containing the following coupler (samples 9 to 14) )created.

First layer: emulsion layer 2.9 g of gelatin, 0.55 g of a blue-sensitive silver chlorobromide emulsion (containing 96 mol% of silver chloride) and 1.5 of dibutyl phthalate
A blue-sensitive emulsion layer comprising 22.5 × 10 ^-4 mol of the following coupler dissolved in g.

Second layer: protective layer A protective layer containing 0.5 g of gelatin. In addition, as a hardening agent,
4-Dichloro-6-hydroxy-s-triazine sodium salt was added at 0.017 g / g of gelatin.

Each of the samples obtained above was subjected to wedge exposure according to a conventional method, and then subjected to development processing in the following step.

[Reversal processing step] Processing step Temperature Time First development 38 ° C 6 minutes Rinse 38 ° C 2 minutes Inversion 38 ° C 2 minutes Color development 38 ° C 6 minutes Adjustment 38 ° C 2 minutes Bleaching 38 ° C 6 minutes Constant Attached 38 ° C for 4 minutes Rinse with water 38 ° C for 4 minutes Stable Room temperature 1 minute Drying The composition of the treatment liquid is as follows.

[First developer] Sodium tetrapolyphosphate 2.0 g Sodium sulfite 20.0 g Hydroquinone monosulfonate 30.0 g Sodium carbonate (monohydrate) 30.0 g 1-phenyl-4-methyl-4-hydroxymethyl- 3-Pyrazolidone 2.0 g Potassium bromide 2.5 g Potassium thiocyanate 1.2 g Potassium iodide (0.1% solution) 2 ml Add water 1000 ml [Inverting solution] Nitrilotrimethylene phosphonic acid hexasodium salt 3.0 g Stannous chloride (dihydrate) 1.0 g p-Amino phenol 0.1 g Sodium hydroxide 5.0 g Glacial acetic acid 15 ml Add water 1000 ml [Color developing solution] Sodium tetrapolyphosphate 2.0 g Sodium sulfite 7.0 g Sodium triphosphate (12-hydrate) 36.0 g potassium bromide 1.0 g Potassium iodide (0.1% solution) 90 ml Sodium hydroxide 3.0 g Citrazinic acid 1.5 g N-ethyl-N-β-methanesulfonamidoethyl-3-methyl-4-aminoaniline sulfate 11 1.0 g Ethylenediamine 3.0 g Water was added and 1000 ml [Prepared solution] Sodium sulfite 12.0 g Sodium ethylenediaminetetraacetate (dihydrate) 8.0 g Thioglycerin 0.4 ml Glacial acetic acid 3 ml Water was added and 1000 ml [bleach solution] Sodium ethylenediaminetetraacetate (dihydrate) 2.0 g Iron (III) ammonium ethylenediaminetetraacetate (dihydrate) 120.0 g Potassium bromide 100.0 g Add water 1000 ml [Constant liquid] Ammonium thiosulfate 80.0 g Sulfurous acid Sodium 5.0g Sodium bisulfite 5.0g 1000 ml [stabilizing solution] Formalin (37% by weight) 5 ml Konidax (manufactured by Konica Corporation) 5 ml 1000 ml with water added For each of the samples treated above, the light resistance of the dye image was measured in the same manner as in Example 1. Heat and moisture resistance were examined. The results are shown below.

Sample No. Coupler Heat / moisture resistance / light resistance 9 Comparison (a) 82 79 10 Invention (I-9) 90 89 11 Invention (I-10) 88 88 12 Invention (I-16) 91 86 13 Invention ( II-3) 89 90 14 The present invention (II-4) 88 87 As is clear from the above, any of the samples using the coupler of the present invention has a higher dye residual ratio than the sample using the comparative coupler. It can be seen that they are excellent in heat and humidity resistance and light resistance and are robust.

Example 3 On a transparent polyethylene terephthalate film support,
The photothermographic layer comprising a support 1 m ² per following components was coated to create a photothermographic material.

Silver Benztriazole 1.0 g Gelatin 6.5 g Reducing agent ¹⁾ 1.5 g Coupler (I-2) of the present invention 2.0 g Silver iodobromide (in terms of silver) 0.65 g Polyvinylpyrrolidone 1.5 g Benztriazole 0.04 g Inhibitor ²⁾ 0.002 g Hot solvent ³⁾ 7.5 g

[0071]

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After imagewise exposure of the above photosensitive material, it was superposed on an image receiving material obtained by coating polyvinyl chloride on a photographic baryta paper and thermally developed at 150 ° C. for 1 minute. A yellow transfer image was obtained.

[0073]

The photographic coupler according to the present invention can be used as a material for a silver halide color photographic light-sensitive material, and an excellent color image free from a change in hue due to heat, moisture and light can be obtained. It is also effective as a dye-providing substance for photothermographic materials. Further, a silver halide color photographic light-sensitive material capable of forming a color image free from discoloration due to heat, moisture and light was obtained.

Continuation of front page (56) References JP-A-3-240053 (JP, A) JP-A-4-156454 (JP, A) JP-A-2-166446 (JP, A) JP-A-5-100376 (JP) , A) JP-A-8-211579 (JP, A) (58) Fields investigated (Int. Cl. ⁷ , DB name) G03C 7/38 REGISTRY (STN) CAPPLUS (STN)

Claims (3)

(57) [Claims] 1. A photographic coupler represented by the general formula [I]. Embedded image In the formula, R and R ₁ represent a substituent, and m is 0 or 1 to
Represents an integer of 3. When m is an integer of 2 or more, a plurality of Rs may be the same or different. X represents a hydrogen atom or a group which is released by a reaction with an oxidized form of a color developing agent. 2. A photographic coupler represented by the general formula [II]. Embedded image Wherein, R 'and R _1' represents a substituent, m 'is an integer of 0 or 1-3. When m 'is an integer of 2 or more, a plurality of R's may be the same or different. X 'represents a group which is released by a reaction with an oxidized form of the color developing agent. 3. A silver halide color photographic light-sensitive material comprising a silver halide emulsion layer containing at least one photographic coupler represented by the general formula [I] or [II].