JPH11102051A - Silver halide color photographic sensitive material - Google Patents

Abstract

PROBLEM TO BE SOLVED: To enhance color developing performance and to improve the lightfastness of a magenta dye image by incorporating a specified magenta coupler in at least one of green-sensitive silver halide emulsion layers. SOLUTION: At least one of the green-sensitive silver halide emulsion layers included in the photographic constituent layers, which include blue-, green- and red-sensitive silver halide emulsion layers, formed on a support contains the magenta coupler represented by the formula in which R1 is a substituent; R2 is an optionally substituted alkyl or cycloalkyl or aryl group; J1 is a divalent bonding group; J2 is a trivalent bonding group; X is an H atom or a group to be released by reaction with the oxidation product of a color developing agent; and Z is a nonmetallic atomic group necessary to form an N-containing heterocycle. Consequently, a dye image to be formed is stable against heat and light.

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. More specifically, the present invention contains a novel pyrazoloazole type magenta coupler to provide excellent coloring properties, and furthermore to provide heat and light. The present invention relates to a silver halide color photographic light-sensitive material capable of obtaining a stable dye image with respect to light.

[0002]

2. Description of the Related Art In silver halide color photographic light-sensitive materials (hereinafter, also simply referred to as color photographic light-sensitive materials and light-sensitive materials), generally used couplers include yellow couplers composed of open-chain ketomethylene compounds, pyrazolone compounds, and pyrazolone compounds. Magenta couplers composed of zoloazole compounds, phenolic compounds, cyan couplers composed of naphthol compounds and the like are known. Conventionally,
5-Pyrazolone compounds are often used as magenta couplers.

Known pyrazolone magenta couplers include US Pat. Nos. 2,600,788 and 3,519,4.
No. 29, JP-A-49-111631, 57-358
No. 58, etc. However, the Theory of the Photographic Process (The Th
eory of the PhotographicP
process), Macmillan, 4th edition (1977), 3
56-358, Fine Chemicals, CMC Company, vol. 14, No. 8, pages 38-41, as summarized in the Photographic Society of Japan, 1985 Annual Meeting Abstracts, pp. 108-110. Dyes formed from pyrazolone magenta couplers have an undesirable side absorption, and improvement thereof is desired.

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 object of the present invention is attained by the following constitutions.

1. 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 comprising a magenta coupler represented by the following formula (M-1) in at least one of the emulsion layers.

[0012]

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In the formula, R ₁ represents a substituent, and R ₂ represents a substituted or unsubstituted alkyl group, cycloalkyl group or aryl group. J ₁ represents a divalent linking group, and J ₂ represents a trivalent linking group. X represents a hydrogen atom or a group capable of leaving by reaction with an oxidized form of a color developing agent, and Z represents a group of nonmetallic atoms necessary for forming a nitrogen-containing heterocyclic ring.

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 material comprising a magenta coupler represented by the following formula (M-2) in at least one of the emulsion layers.

[0015]

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In the formula, R ₁ represents a substituent, and R ₂ represents a substituted or unsubstituted alkyl group, cycloalkyl group or aryl group. J ₁ represents a divalent linking group; J ₃ represents an alkylene group having 2 carbon atoms between an oxygen atom and a hydroxyl group in the main chain;
Represents either a cycloalkylene group or an arylene group. X represents a hydrogen atom or a group capable of leaving by reaction with an oxidized form of a color developing agent. Z represents a nonmetallic atom group necessary for forming a nitrogen-containing heterocyclic ring.

3. 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 emulsion layers contains a magenta coupler represented by the following formula (M-3).

[0018]

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In the formula, R ₁ represents a substituent, and R ₂ represents a substituted or unsubstituted alkyl group, cycloalkyl group or aryl group. J ₁ represents a divalent linking group; J ₄ represents an alkylene group having 3 carbon atoms between an oxygen atom and a hydroxyl group in the main chain;
Represents either a cycloalkylene group or an arylene group. X represents a hydrogen atom or a group capable of leaving by reaction with an oxidized form of a color developing agent. Z represents a nonmetallic atom group necessary for forming a nitrogen-containing heterocyclic ring.

Hereinafter, the present invention will be described in detail.

In the present invention, the general formulas (M-1) to (M-
The magenta coupler represented by 3) will be described.

In the general formulas (M-1) to (M-3), the substituent represented by R ₁ is an alkyl group, an alkenyl group, an alkynyl group, an aryl group, a heterocyclic group, a halogen atom, an alkoxyl group. Group, aryloxy group, alkoxycarbonyl group, aryloxycarbonyl group, sulfonamide group, sulfamoyl group, ureido group, acyl group, carbamoyl group, amide group, sulfonyl group, amino group, cyano group, nitro group, sulfo group, carboxyl Group,
Examples include a hydroxyl group and the like, and these groups may be further substituted by the above substituents.

Among these, for example, alkyl (for example, methyl group, ethyl group, t-butyl group, etc.), alkenyl, aryl, sulfonamide, halogen atom, heterocycle, sulfonyl, acyl, carbamoyl, sulfamoyl, cyano, Each group such as alkoxy, aryloxy, amino, alkoxycarbonyl, aryloxycarbonyl, and carboxyl is preferable, and an alkyl group is more preferable, and a t-butyl group is particularly preferable.

In the above formulas (M-1) to (M-3), J ₁ represents alkyl, cycloalkyl, alkenyl, aryl, acylamino, sulfonamide, alkylthio, arylthio, halogen atom, heterocyclic ring, sulfonyl, sulfinyl, A divalent group derived from each group of phosphonyl, acyl, carbamoyl, sulfamoyl, cyano, alkoxy, aryloxy, acyloxy, amino, alkylamino, ureido, alkoxycarbonyl, aryloxycarbonyl, carboxyl and the like, and these divalent groups Represents a divalent group that can be formed by combining them, and is preferably a substituted or unsubstituted ethylene group, and typical examples thereof include unsubstituted ethylene and 1,1-dimethylethylene.

In the general formula (M-1), J ₂ is 3
Represents a valent linking group.

In the above formulas (M-2) and (M-3), J ₃ and J ₄ represent an alkylene group, a cycloalkylene group or a cycloalkylene group having 2 or 3 carbon atoms between the oxygen atom and the hydroxyl group in the main chain. Represents an arylene group.

The following are typical examples of the groups represented by J ₃ and J ₄ , but J ₃ and J ₄ are not limited thereto.

[0028]

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In the above formulas (M-1) to (M-3), R ₂ represents a substituted or unsubstituted alkyl group, cycloalkyl group or aryl group.

The alkyl group represented by R ₂ is preferably an alkyl group having 1 to 32 carbon atoms, such as a methyl group, an ethyl group, a propyl group, an isopropyl group, a tert-butyl group, a hexyl group, an octyl group and a dodecyl group. , Hexadecyl group, 2-ethylhexyl group and the like.

When the alkyl group represented by R ₂ has a substituent, the substituent is represented by the general formula (M-1)
The same groups as those for R ₁ in (M-3) can be exemplified.

The cycloalkyl group represented by R ₂ is preferably a cycloalkyl group having 3 to 12 carbon atoms, for example, a cyclopropyl group, a cyclopentyl group, a cyclohexyl group, a 2-hexyl group.
Methylcyclopropyl group, adamantyl group and the like are mentioned as typical examples.

When the cycloalkyl group represented by R ₂ has a substituent, the substituent is represented by the general formula (M-
Examples include the same groups as R ₁ in 1) to (M-3).

The aryl group represented by R ₂ preferably has 6 to 14 carbon atoms, and typical examples thereof include a phenyl group, a 1-naphthyl group and a 2-naphthyl group.

When the aryl group represented by R ₂ has a substituent, the substituent is represented by the general formula (M-1)
The same groups as those for R ₁ in (M-3) can be exemplified.

In the general formulas (M-1) to (M-3), as the group capable of leaving by reaction with the oxidized form of the color developing agent represented by X, for example, a halogen atom (a chlorine atom, a bromine atom, Fluorine atom) and alkoxy, aryloxy, heterocyclic oxy, acyloxy, sulfonyloxy,
Alkoxycarbonyloxy, aryloxycarbonyloxy, alkyloxalyloxy, alkoxyoxalyloxy, alkylthio, arylthio, heterocyclic thio, alkyloxythiocarbonylthio, acylamino, sulfonamide, nitrogen-containing heterocyclic ring bonded with an N atom,
Alkyloxycarbonylamino, aryloxycarbonylamino, each group such as carboxyl,
Preferably it is a halogen atom, especially a chlorine atom.

In the general formulas (M-1) to (M-3), examples of the nitrogen-containing heterocyclic ring formed by Z include a pyrazole ring, an imidazole ring, a triazole ring, and a tetrazole ring. Preferred skeletons of the magenta couplers represented by formulas (M-1) to (M-3) are the following [I] and [II], and more preferably [I].

[0038]

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Hereinafter, the general formulas (M-1) to (M)
Representative specific examples of the magenta coupler represented by -3) are shown below, but the present invention is not limited thereto.

[0040]

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[0041]

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[0042]

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[0043]

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[0044] 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
3574, British Patent 1,410,846, New Experimental Chemistry Course 14-III, pp. 1585 to 1594 (197
7), Maruzen, Helv. Chem. Acta. , 36
Volume, 75 (1953); Am. Chem. So
c. 72, 2762 (1950); Org. Sy
nth. , 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 of the present invention.

Synthesis Example 1 << Synthesis of Exemplified Compound MC-1 >>

[0047]

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To 27.0 g of the compound [A], 300 ml of dehydrated dimethylformamide was added, 5 ml of sodium hydride was added, and the mixture was heated to 80 ° C. 25 g of compound [B] was added, and after 5 hours, the reaction was completed.
8 ml of an 8% aqueous ammonia solution was added. After completion of the reaction, ethyl acetate was added to remove the aqueous layer, and then the solvent, ethyl acetate, was distilled off under reduced pressure.
1) 2.59 g was obtained.

Identification was performed by MASS and NMR spectra, and it was confirmed that the compound was Exemplified Compound MC-1.

Synthesis Example 2 << Synthesis of Exemplified Compound MC-9 >>

[0051]

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Compound [D] was added to 33.1 g of Compound [C].
17.5 g and 300 ml of dimethylformamide and 2
10 ml of an 8% methanol solution of sodium methylate was added, and the mixture was heated at 100 ° C. for 2 hours. After completion of the reaction, the reaction mixture was cooled, poured into water, and the obtained solid was washed with nitrile / water to obtain 18.7 g of compound [E] as a white solid.

8.4 g of the obtained compound [E] and 1.5 g of palladium carbon were added to 50 ml of ethanol and hydrogenated under normal pressure. After completion of the reaction, palladium carbon was filtered off, and the filtrate was concentrated. By recrystallizing the obtained residue from nitrile, 6.22 g of compound (F) was obtained.

To 1.96 g of the compound (F) obtained above, 10 ml of ethyl acetate and 1.2 ml of pyridine were added. 1.69 g of compound (G) is slowly added thereto,
Stir at room temperature for 5 hours. After completion of the reaction, the aqueous layer was removed, and the obtained organic layer was washed successively with dilute aqueous hydrochloric acid, dilute aqueous sodium hydrogen carbonate solution and brine. Ethyl acetate as a solvent was distilled off under reduced pressure, and the obtained residue was purified by column chromatography to obtain 2.74 g of a pale yellow oily exemplary compound (MC-9).

Identification was carried out by MASS and NMR spectra, and it was confirmed that the compound was Exemplified Compound MC-9.

The magenta couplers of the present invention represented by formulas (M-1) to (M-3) are represented by the following formula [AO-I]
And / or an image stabilizer represented by the general formula [AO-II].

[0057]

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In the formula, R ₁₂₁ represents a hydrogen atom, an alkyl group, an aryl group, a heterocyclic group or the following residue.

[0059]

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Here, R _121a , R _121b and R _121c each represent a monovalent organic group. R ₁₂₂ , R ₁₂₃ , R ₁₂₄ , R
Each of ₁₂₅ and R ₁₂₆ represents a hydrogen atom, a halogen atom, or a group that can be substituted on a benzene ring. Also, R _{121 to} R
₁₂₆ may combine with each other to form a 5- to 6-membered ring.

[0061]

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In the formula, R ₁₃₁ represents an aliphatic group or an aromatic group, and Y represents a nonmetallic atom group necessary for forming a 5- to 7-membered ring together with a nitrogen atom.

In the general formula [AO-I], R ₁₂₁
Alkyl group, an aryl group represented by, as the heterocyclic group, in the general formula (M-1) ~ (M -3), the alkyl group represented by R ₂ or the like, the groups described as the aryl group, a heterocyclic Examples of the group include a pyrazole group, a 2-imidazolyl group, a 3-pyridyl group, a 2-furyl group and the like. As the R ₁₂₁ a, R ₁₂₁ b, a monovalent organic group represented by R ₁₂₁ c, an alkyl group, an aryl group, an alkoxy group, an aryloxy group, a halogen atom. R ₁₂₁ is preferably a hydrogen atom or an alkyl group. R _{122 to} R ₁₂₆
As a group that can be substituted on the benzene ring represented by the above formula, when the alkyl group, aryl group, or the like represented by R ₂ or the like in the general formulas (M-1) to (M-3) is further substituted And the groups described as the substituents. R ₁₂₂ , R
_{As 123} , R ₁₂₅ and R ₁₂₆ , a hydrogen atom, a hydroxy group,
Preferred are an alkyl group, an aryl group, an alkoxy group, an aryloxy group and an acylamino group, and R ₁₂₄ is preferably an alkyl group, a hydroxy group, an aryl group, an alkoxy group and an aryloxy group. The R ₁₂₁ and R ₁₂₂ may form a closed ring and 5- or 6-membered ring together, R ₁₂₄ at that time
Is preferably a hydroxy group, an alkoxy group, or an aryloxy group. R ₁₂₁ and R ₁₂₂ may be closed to form a methylenedioxy ring. Furthermore, R ₁₂₃ and R ₁₂₄ may be closed to form a 5-membered hydrocarbon ring.
₁₂₁ is preferably an alkyl group, an aryl group, or a heterocyclic group.

The specific examples of the compounds represented by the general formula [AO-I] are shown below.

[0065]

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[0066]

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In addition to the specific examples described above, the above-mentioned general formula [AO-
Specific examples of the compounds represented by the formula (I)
Exemplified compounds A-1 to A-28 described on pages 11 to 13 of JP-A-262159 and Exemplified compounds PH-1 described on pages 8 to 10 of JP-A-61-145552.
PH-29, from page 6 of JP-A-1-306846
Exemplified compounds B-1 to B-21, 2-
Exemplified Compounds I-1 to I-13, I'-1 to I'-8, and II-1 to 958 described on pages 10 to 18 of JP-A-958
II-12, II'-1 to II'-21, III-8 to III-1
4, IV-1 to IV-24, V-13 to V-17, 3-3
Exemplary compounds II-1 to II-33 described on pages 10 to 11 of JP-A-9956 can be exemplified.

Next, in the general formula [AO-II],
R131 represents an aliphatic group or an aromatic group, preferably an alkyl group, an aryl group, or a heterocyclic group, and most preferably an aryl group. Examples of the heterocyclic ring formed by Y together with the nitrogen atom include a piperidine ring, a piperazine ring, a morpholine ring, a thiomorpholine ring, a thiomorpholine-1,1-dione ring, a pyrrolidine ring and the like.

Specific examples of the compound represented by the general formula [AO-II] are shown below.

[0070]

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In addition to the specific examples described above, the above-mentioned general formula [AO-
Illustrative examples of the compound represented by the formula [II]
Illustrative compounds B-1 to B-65 described on pages 8 to 11 of JP-A-67543, and illustrative compounds (1) to (12) described on pages 4 to 7 of JP-A-63-95439.
0) and the like.

The formula [AO-I] and the formula [AO
-II] is used in an amount of 5 to 400 mol% with respect to the magenta coupler represented by formulas (M-1) to (M-3) of the present invention. Is more preferable, and more preferably 10 to 250 mol%.

The magenta couplers of the present invention represented by formulas (M-1) to (M-3) and the image stabilizer are preferably used in the same layer, but adjacent to the layer where the coupler is present. An image stabilizer may be used in the layer to be formed.

The magenta couplers of the present invention represented by formulas (M-1) to (M-3) are generally used in an amount of 1 × 10 ^-3 mol to 8 × 10 ^-1 mol, preferably 1 × 10 ^-3 mol per silver halide.
It can be used in the range of 10 ⁻² mol to 8 × 10 ⁻¹ mol.

The magenta couplers represented by formulas (M-1) to (M-3) of the present invention can be used in combination with other types of magenta couplers.

In order to incorporate the magenta couplers represented by formulas (M-1) to (M-3) of the present invention, a conventional method, for example, a known method such as dibutyl phthalate or tricresyl phosphate, is used. Magenta couplers represented by formulas (M-1) to (M-3) may be used alone or in combination with a mixture of a boiling solvent and a low-boiling solvent such as butyl acetate or ethyl acetate, or a solvent containing only a low-boiling solvent. After mixing and dissolving with a gelatin aqueous solution containing a surfactant, and then emulsifying and dispersing using a high-speed rotary mixer or a colloid mill or an ultrasonic disperser, a method of directly adding to the emulsion is adopted. be able to. Alternatively, the emulsified dispersion may be set, then cut into pieces, washed with water, and then added to the emulsion.

The magenta couplers represented by formulas (M-1) to (M-3) of the present invention can be separately dispersed in a high-boiling solvent and the above-mentioned dispersion method and added to a silver halide emulsion. Preferably, a method in which both compounds are simultaneously dissolved, dispersed, and added to the emulsion is preferred.

The amount of the high boiling point solvent to be added is preferably 0.01 to 10 g, more preferably 0 to 10 g, based on 1 g of the magenta coupler represented by formulas (M-1) to (M-3) of the present invention. 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.

An antifoggant, a stabilizer and the like can be added to the silver halide emulsion. 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 light-sensitive material of the present invention, an image stabilizer and an ultraviolet absorber can be used for the purpose of preventing deterioration of a 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, a generally known color photographic processing can be performed after exposure.

[0086]

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 in which polyethylene was laminated on one side of a paper support and polyethylene containing titanium oxide was laminated on the other side, titanium oxide was used for 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.

[0088]

[Table 1]

[0089]

[Table 2]

The coating solution was prepared as follows.

First layer coating solution 26.7 g of yellow coupler (EY-1), 10.0 g of dye image stabilizer (ST-1), dye image stabilizer (S
T-2) 6.67 g, stain inhibitor (HQ-1) 0.
60 cc of ethyl acetate was added to and dissolved in 67 g of 6.67 g of a high boiling point organic solvent (DNP), and the solution was dissolved in 220 cc of a 10% aqueous gelatin solution containing 7 cc of a 20% aqueous surfactant (SU-2) solution using an ultrasonic homogenizer. This was emulsified and dispersed to prepare a yellow coupler dispersion.

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

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.

[0095]

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[0096]

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[0097]

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[0098]

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[0099]

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The silver halide emulsions used for the first, third and fifth layers are as follows. The chemical sensitizer, stabilizer and sensitizing dye used in each emulsion are also shown below.

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-14 4 × 10 ^-4 mol / mol AgX sensitizing dye BS-21 × 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 Chloroauric 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 R) 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 / Molar AgX stabilizer STAB-1 6 × 10 ^-4 mol / mol AgX sensitizing dye RS-1 1 × 10 ^-4 mol / mol AgX

[0102]

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Next, the same procedure as in Sample 101 was carried out except that the magenta coupler EM-1 in the third layer of Sample 101 was replaced with the magenta coupler of the present invention shown in Table 3 below in an equimolar amount to the amount of magenta coupler EM-1 added. Thus, Samples 102 to 110 were produced.

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 brightener (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 diaminetetraacetate dihydrate 60 g Ethylenediaminetetraacetic 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 was added to make the total amount 1000 cc, and sulfuric acid or water was added. 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.

[0113]

[Table 3]

As is clear from Table 3, Samples 102 to 110 using the magenta coupler of the present invention are superior in both color development and light resistance as compared with Sample 101 using the comparative magenta coupler. .

[0115]

As demonstrated in the examples, the silver halide color photographic light-sensitive material according to the present invention has an excellent effect in that it has excellent color-forming properties, and further has a remarkably improved light fastness of a magenta dye image.

 ──────────────────────────────────────────────────続 き Continuing on the front page (72) Inventor Takashi Suzuki 1 Konica Corporation, Sakura-cho, Hino-shi, Tokyo

Claims (3)

[Claims] 1. 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 material comprising a magenta coupler represented by the following formula (M-1) in at least one of the green-sensitive silver halide emulsion layers. Embedded image [In the formula, R ₁ represents a substituent, and R ₂ represents a substituted or unsubstituted alkyl group, cycloalkyl group or aryl group. J ₁ represents a divalent linking group, and J ₂ represents a trivalent linking group. X represents a hydrogen atom or a group capable of leaving by reaction with an oxidized form of a color developing agent, and Z represents a group of nonmetallic atoms necessary for forming a nitrogen-containing heterocyclic ring. ] 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 comprising a magenta coupler represented by the following formula (M-2) in at least one layer of a green-sensitive silver halide emulsion layer. Embedded image [In the formula, R ₁ represents a substituent, and R ₂ represents a substituted or unsubstituted alkyl group, cycloalkyl group or aryl group. J ₁ represents a divalent linking group, and J ₃ represents any one of an alkylene group, a cycloalkylene group and an arylene group having 2 carbon atoms between the oxygen atom and the hydroxyl group in the main chain. X represents a hydrogen atom or a group capable of leaving by reaction with an oxidized form of a color developing agent. Z represents a nonmetallic atom group necessary for forming a nitrogen-containing heterocyclic ring. ] 3. 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 material comprising a magenta coupler represented by the following formula (M-3) in at least one layer of a green-sensitive silver halide emulsion layer. Embedded image [In the formula, R ₁ represents a substituent, and R ₂ represents a substituted or unsubstituted alkyl group, cycloalkyl group or aryl group. J ₁ represents a divalent linking group, and J ₄ represents any one of an alkylene group, a cycloalkylene group and an arylene group having 3 carbon atoms between the oxygen atom and the hydroxyl group in the main chain. X represents a hydrogen atom or a group capable of leaving by reaction with an oxidized form of a color developing agent. Z represents a nonmetallic atom group necessary for forming a nitrogen-containing heterocyclic ring. ]