JPH1031291A - Silver halide color photographic sensitive material - Google Patents

Abstract

PROBLEM TO BE SOLVED: To enhance color developing performance and to improve remarkably the lightfastness of a magenta dye image by incorporating at least one kind of specified coupler in at least one of green-sensitive silver halide emulsion layers. SOLUTION: The silver halide color photographic sensitive material has photographic constituent layers comprising blue-, green-, and red-sensitive silver halide emulsion layers on a support and at least one of the green-sensitive silver halide emulsion layers contains at least one of the couplers represented by the formula in which R1 is a substituent; R2 is an atom or an alkyl or aryl group; R3 is an alkyl, aryl, -COR4 , -CONHR4 , -NHCOR4 , -NHCO2 R4 , -NHCONHR4 , -NHR4 , -NH(R4 )2 , or the like; R4 is an optionally substituted alkyl or aryl group; and X1 is H atom or a group to be released by reaction with the oxidation product of a color developing agent.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a silver halide color photographic light-sensitive material containing a magenta coupler, and more particularly, to containing a novel pyrazolotriazole-based magenta coupler to provide excellent color reproducibility and coloring. Further, the present invention relates to a silver halide color photographic material capable of obtaining a dye image stable to heat and light.

[0002]

2. Description of the Related Art In a silver halide color photographic light-sensitive material, couplers generally used include a yellow coupler composed of an open-chain ketomethylene compound, a magenta coupler composed of a pyrazolone compound and a pyrazoloazole compound, a phenol compound and a naphthol compound. Cyan couplers composed of compounds are known.

Heretofore, 5-pyrazolone compounds have been frequently used as magenta couplers. Known pyrazolone magenta couplers include U.S. Pat.
Nos. 88 and 3,519,429, JP-A-49-111
No. 631, No. 57-35858 and the like.
However, the Theory of the Photographic Process (The Theory of the P
Photographic Process), Macmillan, 4th edition (1977), pp. 356-358, Fine Chemicals, CMC, vol. 14, No. 8, 38.
As described in the Abstracts of the Photographic Society of Japan, Annual Meeting of 1985, pp. 108-110, dyes formed from pyrazolone magenta couplers have undesirable side absorption, and improvement thereof is desired. ing.

As described in the above literature, a dye formed from a pyrazoloazole magenta coupler has no side absorption. The fact that this coupler is a good coupler is described in the above-mentioned documents in U.S. Pat. Nos. 3,725,067, 3,758,309 and 3,810,761.

However, the light fastness of azomethine dyes formed from these couplers is remarkably low, which significantly impairs the performance of color photographic light-sensitive materials, especially print-based color photographic light-sensitive materials.

[0006] Conventionally, studies have been made to improve the light fastness. For example, JP-A-59-12573
No. 2, 61-282845, 61-29239
And JP-A-61-279855 disclose a technique of using a phenolic compound or a phenyl ether compound in combination with a pyrazoloazole-based magenta coupler.
No. 6, No. 62-208048, No. 62-157031
And No. 63-163351 disclose a technique using an amine compound in combination.

Further, JP-A-63-24256 proposes a pyrazoloazole-based magenta coupler having an alkyloxyphenyloxy group.

However, even in the above technique, the light fastness of the magenta dye image is insufficient, and improvement thereof has been strongly desired.

[0009]

DISCLOSURE OF THE INVENTION The present invention has been made to solve the above problems, and an object of the present invention is to provide a halogen which is excellent in color development and has a markedly improved light fastness of a magenta dye image. An object of the present invention is to provide a silver halide color photographic material.

[0010]

The above objects of the present invention have been attained by the following constitutions.

(1) A silver halide color photographic light-sensitive material having a photographic component layer including a blue-sensitive silver halide emulsion layer, a green-sensitive silver halide emulsion layer and a red-sensitive silver halide emulsion layer on a support, A silver halide color photographic light-sensitive material characterized in that at least one of the green-sensitive silver halide emulsion layers contains at least one kind of coupler represented by the following general formula (I).

[0012]

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[Wherein, R ₁ represents a substituent, R ₂ represents a hydrogen atom, an alkyl group or an aryl group, and R ₃ represents an alkyl group, an aryl group, —CO ₂ R ₄ , —CONHR ₄ , and —N
_{HCOR 4, -NHCO 2 R 4,} -NHCONHR 4, -N
_{HR 4, -N (R 4)} 2, -OR 4, -SR 4, -SO 2 R 4
Or an -NHSO ₂ R _4, R ₄ represents an alkyl group or an aryl group. The alkyl group and the aryl group may have a substituent. X ₁ represents a hydrogen atom or a group capable of leaving by reaction with an oxidized form of a color developing agent. (2) In a silver halide color photographic light-sensitive material having a photographic component layer comprising a blue-sensitive silver halide emulsion layer, a green-sensitive silver halide emulsion layer and a red-sensitive silver halide emulsion layer on a support, A silver halide color photographic light-sensitive material, characterized in that at least one of the light-sensitive silver halide emulsion layers contains at least one coupler represented by the following formula (II).

[0014]

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[Wherein, R ₅ represents a substituent, and R ₆ , R ₇ ,
R ₈ and R _{9 each} represent a hydrogen atom, an alkyl group, an aryl group, -C
_{O 2 R 10, -CONHR 10,} -NHCOR 10, -NHC
_{ONHR 10, -NHCO 2 R 10,} -NHR 10, -N (R
₁₀ ) ₂ , -OR ₁₀ , -SR ₁₀ , -SO ₂ R ₁₀ or -NH
Represents SO ₂ R ₁₁ , R ₁₀ represents an alkyl group or an aryl group, and R ₁₁ represents an alkyl group. The alkyl group and the aryl group may have a substituent. X ₂ represents a hydrogen atom or a group capable of leaving by reaction with an oxidized form of a color developing agent. Hereinafter, the present invention will be described more specifically.

In the general formula (I), the substituent represented by R ₁ includes alkyl, cycloalkyl, alkenyl, aryl, acylamino, sulfonamide, alkylthio, arylthio, heterocycle, sulfonyl, sulfinyl, phosphonyl, acyl , Carbamoyl, sulfamoyl, alkoxy, aryloxy, heterocyclic oxy,
Acyloxy, carbamoyloxy, amino, alkylamino, anilino, imide, ureido, sulfamoylamino, alkoxycarbonylamino, aryloxycarbonylamino, alkoxycarbonyl, aryloxycarbonyl, carboxyl, each group such as a halogen atom, more preferably Preferred are alkyl groups, and among the alkyl groups, particularly preferred is a t-butyl group.

The alkyl group represented by R ₂ , R ₃ and R ₄ preferably has 1 to 32 carbon atoms and may be linear or branched.

The aryl group represented by R ₂ , R ₃ and R ₄ is preferably a phenyl group.

The alkyl group or the aryl group represented by R ₂ , R ₃ and R ₄ may have a substituent represented by R ₁ .

Examples of the group capable of leaving by reaction with an oxidized form of the color developing agent represented by X ₁ include, for example, a halogen atom (a chlorine atom, a bromine atom, a fluorine atom, etc.), alkoxy, aryloxy, heterocyclic oxy , Acyloxy, sulfonyloxy, alkoxycarbonyloxy,
Aryloxycarbonyloxy, alkyloxalyloxy, alkoxyoxalyloxy, alkylthio,
Examples include arylthio, heterocyclic thio, alkyloxythiocarbonylthio, acylamino, sulfonamide, nitrogen-containing heterocyclic ring bonded with an N atom, alkyloxycarbonylamino, aryloxycarbonylamino, and carboxyl, preferably halogen. Atoms, especially chlorine atoms.

In the general formula (II), examples of the substituent represented by R ₅ include alkyl, cycloalkyl, alkenyl, aryl, acylamino, sulfonamide, alkylthio, arylthio, heterocycle, sulfonyl, sulfinyl, phosphonyl, acyl , Carbamoyl, sulfamoyl, alkoxy, aryloxy, heterocyclic oxy,
Each group such as acyloxy, carbamoyloxy, amino, alkylamino, anilino, imide, ureido, sulfamoylamino, alkoxycarbonylamino, aryloxycarbonylamino, alkoxycarbonyl, aryloxycarbonyl, carboxyl, and halogen atom is preferable, and further more preferable. Is an alkyl group,
Among the alkyl groups, a t-butyl group is particularly preferred.

The alkyl group represented by R ₆ , R ₇ , R ₈ , R ₉ , R ₁₀ , and R ₁₁ preferably has 1 to 32 carbon atoms, and may be linear or branched.

The aryl group represented by R ₆ , R ₇ , R ₈ , R ₉ and R ₁₀ is preferably a phenyl group.

The alkyl group or the aryl group represented by R ₆ , R ₇ , R ₈ , R ₉ , R ₁₀ , and R ₁₁ can have a substituent represented by R ₅ .

The group capable of leaving by reaction with an oxidized form of the color developing agent represented by X ₂ includes, for example, a halogen atom (a chlorine atom, a bromine atom, a fluorine atom, etc.), alkoxy, aryloxy, heterocyclic oxy , Acyloxy, sulfonyloxy, alkoxycarbonyloxy, aryloxycarbonyloxy, alkyloxalyloxy, alkoxyoxalyloxy, alkylthio, arylthio, heterocyclic thio, alkyloxythiocarbonylthio, acylamino, sulfonamide, Examples include groups such as a nitrogen heterocycle, alkyloxycarbonylamino, aryloxycarbonylamino, and carboxyl, and a halogen atom, particularly a chlorine atom is preferred.

Hereinafter, typical specific examples of the magenta coupler represented by formula (I) or (II) of the present invention will be shown, but the present invention is not limited thereto.

[0027]

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[0028]

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[0029]

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[0030]

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[0031]

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[0032]

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[0033]

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[0034]

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[0035]

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[0036]

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[0037]

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[0038]

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The pyrazoloazole-based magenta coupler of the present invention can be obtained from the Journal of the Chemical Society (Journal of the Chemical Society).
alSociety), Perkin I
(1977), 2047-2052, U.S. Pat.
5,067, JP-A-59-99437, and JP-A-58-4
No. 2045, No. 59-162548, No. 59-171
No. 956, No. 60-33552, No. 60-43659
No., 60-172982, 60-190779
Nos. 61-189538 and 61-241754
Nos. 63-163351 and 62-157031
No., Synthesis, 1981, p. 40, 198
4 years 122 pages, 1984 894 pages, JP-A-49-5
No. 3574, British Patent 1,410,846, New Laboratory Chemistry Course 14-III, pp. 1585-1594 (197)
7), Maruzen, Helv. Chem. Acta. ,
36, 75 (1953); Am. Che
m. Soc. 72, 2762 (1950), O
rg. Synth. , Vol. II, p. 395 (1943), and can be easily synthesized by those skilled in the art.

The following is a typical synthesis example of the magenta coupler represented by formula (I) or (II) of the present invention.

Synthesis Example 1 << Synthesis of Exemplified Compound (I-1) >>

[0042]

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<Synthesis of Intermediate (II)> 24.4 g (0.10 mol) of α-hydroxymyristic acid (I) was added to 100
Dissolve in ethyl acetate and add 7.9 g (0.10 g)
Mol) of acetyl chloride, and the mixture was heated under reflux for 2 hours. After cooling the reaction solution, the solvent was distilled off under reduced pressure to obtain 27.0 g of the intermediate (II) (yield 97.8%).

<Synthesis of Intermediate (III)> Intermediate (II) 2
5.0 g (0.091 mol) was dissolved in 150 ml of toluene, and 17.9 g (0.15 mol) of thionyl chloride was added thereto, followed by heating under reflux for 3 hours. After the completion of the reaction, the solvent and excess thionyl chloride were distilled off under reduced pressure to obtain 26.7 g of a slightly brown solid intermediate (III) (yield 93.4%).

<Synthesis of Intermediate (V)> Intermediate (IV) 1
6.8 g (0.080 mol) were dissolved in 200 ml of acetonitrile, and 25.2 g of the intermediate (III) (0.
080 mol) and heated under reflux for 2 hours. After completion of the reaction, the solvent was distilled off under reduced pressure. Toluene 150 in residue
Then, 2 ml of sulfuric acid and 2 ml of sulfuric acid were added, and the mixture was heated under reflux for 2 hours while removing water produced by an ester tube. After completion of the reaction, the solvent was distilled off under reduced pressure, and 300 ml of ethyl acetate and 100 ml of a saturated aqueous solution of sodium hydrogen carbonate were added to the residue, and the ethyl acetate layer was separated and extracted. Further, the ethyl acetate layer was washed with water, dried over anhydrous magnesium sulfate, and ethyl acetate was distilled off under reduced pressure to obtain a pale yellow oily intermediate (V).
2.7 g was obtained (88.2% yield).

<Synthesis of Intermediate (VI)> Acetic anhydride was added to 32.0 g (0.073 mol) of a crude product of Intermediate (V).
Then, the mixture was heated under reflux for 2 hours. Thereafter, heating was further continued while removing excess acetic anhydride, and after the distillation was completed, the reaction solution was cooled to room temperature. 100 ml of methanol and 25 ml of concentrated hydrochloric acid were added thereto, and the mixture was refluxed again for 2 hours. The reaction solution was cooled at room temperature, and the precipitated sulfur was separated by filtration. The filtrate was concentrated under reduced pressure, 200 ml of ethyl acetate was added, the mixture was neutralized with an aqueous sodium hydroxide solution, and the organic layer was extracted. The organic layer was washed with water and dried over anhydrous magnesium sulfate, and then ethyl acetate was distilled off under reduced pressure to obtain 21.7 g of a brown oily intermediate (VI) (yield: 82.2%).

<Synthesis of Exemplified Compound (I-1)> 21 g (0.058 mol) of the intermediate (VI) was dissolved in 150 ml of ethyl acetate and cooled to 5 ° C. The temperature of the reaction solution is 5-1
While maintaining the temperature at 0 ° C, 8.0 g (0.060 mol) of N-chlorosuccinimide was added little by little. After continuing stirring at 5 ° C. for 2 hours, the reaction solution was washed with water. After the organic layer was dispersed and extracted, dried over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure. The obtained crude product was recrystallized from a mixed solvent of ethyl acetate and hexane to give the target compound (I) as a white powder.
-1) was obtained (15.9 g, yield 69.1%).

Identification was carried out by MASS, NMR and IR spectra, and it was confirmed that each of the intermediates was Compound (I-1).

Synthesis Example 2 << Synthesis of Exemplified Compound II-1 >>

[0050]

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<Synthesis of Intermediate (II ′)> 31.4 g (0.10 mol) of α-hydroxymethylstearic acid (I ′) was dissolved in 150 ml of ethyl acetate, and 7.9 was added thereto.
g (0.10 mol) of acetyl chloride was added, and the mixture was heated under reflux for 3 hours. After cooling the reaction mixture, the solvent was distilled off under reduced pressure.
4.1 g of the intermediate (II ') was obtained (yield 95.8%).

<Synthesis of Intermediate (III ′)>
I ′) 32.0 g (0.09 mol) was dissolved in 200 ml of toluene, and 17.9 g (0.1%) of thionyl chloride was added thereto.
5 mol) and heated under reflux for 4 hours. After completion of the reaction, the solvent and excess thionyl chloride were distilled off under reduced pressure to obtain an intermediate (II
3 ′ g of I ′) was obtained (91.1% yield).

<Synthesis of Intermediate (V ′)> Intermediate (IV) 1
6.8 g (0.080 mol) was dissolved in 200 ml of acetonitrile, 30.0 g of the intermediate (III ') was added, and the mixture was heated under reflux for 3 hours. After completion of the reaction, the solvent was distilled off under reduced pressure. 150 ml of toluene and 2 ml of sulfuric acid are added to the residue, and water is removed by an ester tube while removing water.
Heated to reflux for an hour. After completion of the reaction, the solvent was distilled off under reduced pressure, and then 300 ml of ethyl acetate and 100 ml of a saturated aqueous sodium hydrogen carbonate solution were added and mixed. Thereafter, the ethyl acetate layer was separated, washed with water, and then dried over anhydrous magnesium sulfate. Thereafter, the solvent was distilled off under reduced pressure to obtain 31.6 g of a pale yellow oily intermediate (V ') (yield: 7).
8.0%).

<Synthesis of Intermediate (VI ′)> Intermediate (V ′)
30.4 g (0.060 mol) of acetic anhydride
After adding 00 ml, the mixture was heated under reflux for 2 hours. Thereafter, heating was further continued while distilling off excess acetic anhydride.
The reaction was cooled to room temperature. 10 to the cooled reaction mixture
0 ml of methanol and 20 ml of concentrated hydrochloric acid were added, and the mixture was refluxed again for 2 hours. The reaction solution was cooled at room temperature, and the precipitated sulfur was separated by filtration. After the filtrate was concentrated under reduced pressure, 200 ml of ethyl acetate was added and neutralized with an aqueous sodium hydroxide solution. After washing the organic layer with water and drying over anhydrous magnesium sulfate, ethyl acetate was distilled off under reduced pressure to obtain 19.4 g of a brown oily intermediate (VI ') (yield: 74.8%).

<Synthesis of Exemplified Compound (II-1)> 18 g (0.042 mol) of the intermediate (VI ') was dissolved in 100 ml of ethyl acetate and cooled to 5 ° C. The temperature of the reaction solution
While maintaining the temperature at 10 ° C., 5.6 g (0.042 mol) of N-
Chlorosuccinimide was added in small portions. After stirring at 5 ° C. for 3 hours, the reaction solution was washed with water. The organic layer was separated, dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The obtained crude product was recrystallized from a mixed solvent of ethyl acetate and hexane to give the target compound (II-
12.7 g of 1) was obtained (yield: 64.7%).

Identification was carried out by MASS, NMR and IR spectra, and it was confirmed that each of the intermediates was exemplified compound (II-1).

The general formula (I) or the general formula (II) of the present invention
(Hereinafter, also referred to as the magenta coupler of the present invention) can be used in combination with other types of magenta couplers.

In order to incorporate the magenta coupler of the present invention, a conventional method, for example, a mixed solution of a known high-boiling solvent such as dibutyl phthalate or tricresyl phosphate and a low-boiling solvent such as butyl acetate or ethyl acetate is used. Alternatively, after dissolving the magenta coupler of the present invention alone or in combination in a solvent having only a low boiling point solvent,
A method of mixing with a gelatin aqueous solution containing a surfactant, emulsifying and dispersing using a high-speed rotating mixer, a colloid mill or an ultrasonic dispersing machine, and then directly adding the resulting emulsion to the emulsion can be adopted. Alternatively, the emulsified dispersion may be set, then cut into pieces, washed with water, and then added to the emulsion. The magenta coupler of the present invention may be separately dispersed in a high-boiling solvent and the dispersion method and added to the silver halide emulsion, but a method in which both compounds are simultaneously dissolved, dispersed, and added to the emulsion is preferable. .

The amount of the high boiling point solvent to be added is preferably from 0.01 to 10 based on 1 g of the magenta coupler of the present invention.
g, more preferably in the range of 0.1 to 3.0 g.

As the silver halide emulsion used in the light-sensitive material of the present invention, any conventional silver halide emulsion can be used. The emulsion can be chemically sensitized by a conventional method, and can be optically sensitized to a desired wavelength region by using a sensitizing dye. Antifoggants,
Stabilizers and the like can be added. It is advantageous to use gelatin as a binder for the emulsion.

The emulsion layer and other hydrophilic colloid layers can be hardened, and can contain a plasticizer and a dispersion (latex) of a water-insoluble or hardly soluble synthetic polymer. A coupler is used in an emulsion layer of a color photographic light-sensitive material.

Further, a development accelerator, a bleaching accelerator, a developer, a silver halide solvent, a toning agent, and a coupling reaction with a colored coupler, a competing coupler, and an oxidized form of a developing agent having a color correcting effect. Compounds that release photographically useful fragments such as hardeners, foggants, antifoggants, chemical sensitizers, spectral sensitizers and desensitizers can be used.

In the photographic material of the present invention, an image stabilizer and an ultraviolet absorber can be used for the purpose of preventing deterioration of the dye image.

As the support, paper laminated with polyethylene or the like, polyethylene terephthalate film, baryta paper, cellulose triacetate or the like can be used.

In order to obtain a dye image using the light-sensitive material of the present invention, generally known color photographic processing can be performed after exposure.

[0066]

Next, the present invention will be described based on examples, but embodiments of the present invention are not limited to these examples.

Example 1 On a support obtained by laminating polyethylene on one side of a paper support and polyethylene containing titanium oxide on the other side, titanium oxide was applied to each layer having the structure shown in Tables 1 and 2 below. The sample was applied on the side of the polyethylene layer to be prepared, whereby a multilayer color photographic material sample 101 was prepared.

[0068]

[Table 1]

[0069]

[Table 2]

The coating solution was prepared as follows. First layer coating solution Yellow coupler (EY-1) 26.7 g, dye image stabilizer (ST-1) 10.0 g, dye image stabilizer (ST-2) 6.67 g, stain inhibitor (HQ-) 1)
0.67 g and 6.67 g of high boiling point organic solvent (DNP)
Add 60 cc of ethyl acetate to the mixture and dissolve it.
10% containing 7 cc of surfactant (SU-2) aqueous solution
A 220 μg aqueous gelatin solution was emulsified and dispersed using an ultrasonic homogenizer to prepare a yellow coupler dispersion.

This dispersion was mixed with a blue-sensitive silver halide emulsion (containing 8.67 g of silver) shown below, and an anti-irradiation dye (AIY-1) was further added to prepare a coating solution for the first layer.

The coating solutions for the second to seventh layers were prepared in the same manner as the coating solution for the first layer. (HH-1) was added to the second and fourth layers as a hardener, and (HH-2) was added to the seventh layer. Surfactants (SU-1), (SU-
3) was added to adjust the surface tension.

The structural formulas of the compounds used in each of the above-mentioned layers are shown below.

[0074]

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[0075]

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[0076]

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[0077]

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[0078]

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The silver halide emulsions used for the first, third and fifth layers are as follows.

Blue-sensitive silver halide emulsion (Em-B) Monodispersed cubic silver chlorobromide emulsion having an average particle size of 0.85 μm, a coefficient of variation of 0.07, and a silver chloride content of 99.5 mol%. Sodium thiosulfate 0 0.8 mg / mol AgX chloroauric acid 0.5 mg / mol AgX stabilizer STAB-1 6 × 10 ⁻⁴ mol / mol AgX sensitizing dye BS-1 4 × 10 ⁻⁴ mol / mol AgX sensitizing dye BS-2 1 × 10 ⁻⁴ mol / mol AgX green-sensitive silver halide emulsion (Em-G) Monodispersed cubic silver chlorobromide having an average particle size of 0.43 μm, a coefficient of variation = 0.08, and a silver chloride content of 99.5 mol%. Emulsion Sodium thiosulfate 1.5 mg / mol AgX Chloroic acid 1.0 mg / mol AgX Stabilizer STAB-1 6 × 10 ^-4 mol / mol AgX Sensitizing dye GS-1 4 × 10 ^-4 mol / mol AgX Red sensitivity Silver halide emulsion (Em- ) Monodisperse cubic silver chlorobromide emulsion having an average particle size of 0.50 µm, a coefficient of variation of 0.08, and a silver chloride content of 99.5 mol% Sodium thiosulfate 1.8 mg / mol AgX chloroauric acid 2.0 mg / mol AgX stabilizer STAB-1 6 × 10 ⁻⁴ mol / mol AgX sensitizing dye RS-1 1 × 10 ⁻⁴ mol / mol AgX

[0081]

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Next, the coupler EM-
Samples 102 to 119 were produced in the same manner as in Sample 101 except that 1 was replaced with the coupler of the present invention or a comparative coupler shown in Table 3 below in an equimolar amount to the amount of coupler EM-1 added.

Each of the samples thus prepared was subjected to wedge exposure with green light according to a conventional method, and then processed according to the following processing steps.

Processing Step Temperature Time Color Development 35.0 ± 0.3 ° C. 45 seconds Bleaching and Fixing 35.0 ± 0.5 ° C. 45 seconds Stabilization 30-34 ° C. 90 seconds Drying 60-80 ° C. 60 seconds The composition of each processing solution is shown below. The replenishment amount of each processing solution is 80 cc per m ^{2 of the} color photographic light-sensitive material.

Color developing solution Tank solution Replenisher Pure water 800 cc 800 cc Triethanolamine 10 g 18 g N, N-diethylhydroxylamine 5 g 9 g Potassium chloride 2.4 g -1-Hydroxyethylidene-1,1-diphosphonic acid 1.0 g 1. 8 g N-ethyl-N-β-methanesulfonamidoethyl-3-methyl-4-aminoaniline sulfate 5.4 g 8.2 g Fluorescent whitening agent (4,4′-diaminostilbene disulfonic acid derivative) 1.0 g 1 8.8 g Potassium carbonate 27 g 27 g Water was added to make the total volume 1000 cc. The pH of the tank solution was 10.10, and the pH of the replenisher was 10.
Adjust to 60.

Bleaching / fixing solution (tank solution and replenisher are the same) Ferric ammonium ammonium diamine tetraacetate dihydrate 60 g Ethylene diamine tetraacetic acid 3 g Ammonium thiosulfate (70% aqueous solution) 100 cc Ammonium sulfite (40% aqueous solution) 27.5 cc water In addition, the total amount is adjusted to 1000 cc, and the pH is adjusted to 5.7 with potassium carbonate or glacial acetic acid.

Stabilizing solution (the tank solution and the replenishing solution are the same) 5-chloro-2-methyl-4-isothiazolin-3-one 1.0 g ethylene glycol 1.0 g 1-hydroxyethylidene-1,1-diphosphonic acid 2 1.0 g Ethylenediaminetetraacetic acid 1.0 g Ammonium hydroxide (20% aqueous solution) 3.0 g Optical brightener (4,4'-diaminostilbene disulfonic acid derivative) 1.5 g Water is added to make the total amount 1000 cc, and sulfuric acid or water Adjust the pH to 7.0 with potassium oxide.

The following evaluation was performed using the sample after the continuous treatment.

<< Dmax >> The maximum color density was measured.

<< Light Resistance >> The obtained sample was irradiated with a xenon fade meter for 10 days, and the residual ratio (%) of the dye image at an initial density of 1.0 was determined.

Table 3 shows the results.

[0092]

[Table 3]

As is clear from Table 3, samples 101 to 1
19, Samples 102 to 102 using the coupler of the present invention
119 showed good color development and a very large improvement in light resistance as compared with Sample 101 using the comparative coupler.

[0094]

As demonstrated in the Examples, the silver halide color photographic light-sensitive material according to the present invention has excellent color-forming properties, and the light fastness of a magenta dye image is remarkably improved, so that an excellent image can be obtained.

Claims (2)

[Claims] 1. A silver halide color photographic light-sensitive material comprising a support having thereon a photographic component layer comprising a blue-sensitive silver halide emulsion layer, a green-sensitive silver halide emulsion layer and a red-sensitive silver halide emulsion layer. A silver halide color photographic light-sensitive material, characterized in that at least one green-sensitive silver halide emulsion layer contains at least one coupler represented by the following formula (I). Embedded image [Wherein, R ₁ represents a substituent, R ₂ represents a hydrogen atom, an alkyl group or an aryl group, and R ₃ represents an alkyl group, an aryl group, -CO ₂ R ₄ , -CONHR ₄ , -NHCOR ₄ ,-
_{NHCO 2 R 4, -NHCONHR 4,} -NHR 4, -N
(R ₄ ) ₂ , —OR ₄ , —SR ₄ , —SO ₂ R _4, or —NH
Represents SO ₂ R ₄ , wherein R ₄ represents an alkyl group or an aryl group. The alkyl group and the aryl group may have a substituent. X ₁ represents a hydrogen atom or a group capable of leaving by reaction with an oxidized form of a color developing agent. ] 2. A silver halide color photographic light-sensitive material having a photographic component layer comprising a blue-sensitive silver halide emulsion layer, a green-sensitive silver halide emulsion layer and a red-sensitive silver halide emulsion layer on a support. A silver halide color photographic light-sensitive material, characterized in that at least one green-sensitive silver halide emulsion layer contains at least one coupler represented by the following formula (II). Embedded image [Wherein, R ₅ represents a substituent, and R ₆ , R ₇ , R ₈ , and R ₉ are
Hydrogen atom, an alkyl group, an aryl group, -CO ₂ R _10, -
CONHR ₁₀ , —NHCOR ₁₀ , —NHCONHR ₁₀ ,
_{-NHCO 2 R 10, -NHR 10,} -N (R 10) 2, -OR
_10, -SR _10, represents -SO ₂ R ₁₀ or -NHSO ₂ R _11, R ₁₀ represents an alkyl group or an aryl group, R ₁₁ represents an alkyl group. The alkyl group and the aryl group may have a substituent. X ₂ represents a hydrogen atom or a group capable of leaving by reaction with an oxidized form of a color developing agent. ]