JPH07261348A - Silver halide color photographic sensitive material - Google Patents

Abstract

PURPOSE:To obtain a silver halide color photographic sensitive material improved in the light resistance of a dye image and enhanced in image storage stability and color reproduction performance by incorporating a specified magenta coupler. CONSTITUTION:The photosensitive material contains at least one of the magenta couplers represented by the formula in which R1 is a tertiary alkyl; each of R2 and R4 and R5 is H or an alkyl; R3 is an alkyl; R6 is a substituent; R7 is an alkyl substituted alkyl, aryl or substituted aryl and their substituted groups do not include hydroxy, carboxy, or a carboxylic metal salt; L is a divalent a bonding group; each of l, m, and n is an integer of 1-10, 0-5, and 0-5, respectively; and X is H or a group to be released by reaction with the oxidation product of a color developing agent. This magenta coupler can be used together with another kind of coupler and optionally together with various image stabilizers.

Description

Detailed Description of the Invention

[0001]

FIELD OF THE INVENTION The present invention relates to a silver halide color photographic light-sensitive material excellent in image storability and color reproducibility.

[0002]

2. Description of the Related Art Conventionally, a combination of a yellow coupler, a magenta coupler and a cyan coupler is used in a color photographic paper which is directly provided for viewing. Many efforts have been made to date to improve the fastness of color dye images obtained from these couplers and to preserve and continue to utilize them for many years.

However, it is still not sufficient to meet the user's desire to prevent fading and discoloration of dye images in color photographs and to store high quality images semipermanently. In terms of storability in dark places such as albums, significant improvements have been made in recent years, as represented by "Konica Color 100 Years Print", and it has become possible to store photographic images for a long time that is satisfactory. On the other hand, the storage stability in the light (light resistance) under the condition of being exposed to light is still at an insufficient level, and improvement is desired. In particular, among the three color dyes of yellow, magenta, and cyan, the magenta dye has the weakest light resistance, and efforts have been made to improve it.

Further, the recently developed pyrazoloazole-based magenta coupler is different from the conventionally used 5-pyrazolone-based magenta coupler in that the coloring dye has no sub-absorption at around 430 nm, so that the color reproducibility is basically improved. It is known that the magenta dye obtained from the pyrazoloazole-based magenta coupler is inferior in light resistance to the magenta dye obtained from the 5-pyrazolone-based magenta coupler, though it is characterized by being advantageous to However, many improved techniques have been proposed. For example, JP-A-56-1
59644, 59-125732, 61-145552, 60-262159
No. 61-90155, JP-A-3-39956 and the like, and phenol or phenyl ether compounds, JP-A-61
-73152, 61-72246, 61-189539, 61-189540
Nos. 63-95439 and the like amine compounds, JP-A-61-140941, 61-145554, 61-158329, 62-
It is possible to use the metal complexes described in 183459 and the like, the clathrate compounds and heterocyclic compounds described in JP-A 2-100048 and the like. However, when these compounds are used, the color density of the coupler is lowered, color contamination occurs during storage over time, color contamination occurs due to coloring of the added compound itself, and an undesirable change in color tone is caused. Or, the dispersibility of the dispersion containing the coupler may deteriorate, and the stability over time may deteriorate. Further, although the above-mentioned improved technology shows a great effect in improving the light resistance, the light resistance of the magenta dye is nevertheless improved. Is currently inferior to the light resistance of yellow dyes and cyan dyes, and as a result, the color balance of the image is disrupted during the fading process, causing the colors of the photograph to shift toward yellow and cyan, causing unnatural discoloration. There is a problem that it ends up. Further, a technique for improving light resistance by substituting a branched alkyl group having a large steric hindrance in the pyrazolotriazole skeleton is proposed in JP-A-61-65245 and the like, but in this case, light resistance is improved. It was found that the absorption of the generated dye becomes broad, and problems such as a decrease in color development occur. Therefore, in order to improve the light resistance, the development of new technology is strongly demanded.

[0005]

SUMMARY OF THE INVENTION It is, therefore, a first object of the present invention to provide a silver halide color photographic light-sensitive material which has improved light resistance of dye images and excellent image storability. A second object of the present invention is to provide a silver halide color photographic light-sensitive material excellent in color reproducibility.

[0006]

The above objects of the present invention are achieved by the following configurations.

A silver halide color photographic light-sensitive material containing at least one magenta coupler represented by the following general formula [I].

[0008]

[Chemical 2]

In the formula, R ₁ represents a tertiary alkyl group,
R ₂ , R ₄ and R ₅ represent a hydrogen atom or an alkyl group,
R ₃ represents an alkyl group. R ₆ represents a substituent, R ₇
Represents an alkyl group, a substituted alkyl group, an aryl group or a substituted aryl group, and the substituent does not include a hydroxyl group, a carboxy group or a metal salt thereof. L represents a divalent linking group, 1 represents an integer of 1 to 10, m represents an integer of 0 to 5, and n represents an integer of 0 to 5. X represents a hydrogen atom or a group which is released by a reaction with an oxidized product of a color developing agent.

The present invention will be specifically described below.

First, the magenta coupler represented by the general formula [I] of the present invention will be described.

In the above formula [I], R ₁ represents a tertiary alkyl group, preferably t-butyl group.

R ₂ , R ₄ and R ₅ represent a hydrogen atom or an alkyl group, and the alkyl group may be linear or branched, but is preferably a hydrogen atom or a methyl group.

The alkyl group represented by R ₃ is the same as R ₂ and R mentioned above.
It has the same meaning as ₄ , R ₅ , and preferably at least one of R ₂ and R ₃ is a methyl group.

The substituent represented by R ₆ is not particularly limited, but typical examples thereof include alkyl, aryl, anilino, acylamino, sulfonamide, alkylthio, arylthio, alkenyl and cycloalkyl groups. , Halogen atom and cycloalkenyl, alkynyl, heterocycle, sulfonyl, sulfinyl, phosphonyl, acyl, carbamoyl, sulfamoyl, cyano, alkoxy, aryloxy, heterocycleoxy, siloxy, acyloxy, carbamoyloxy, amino, alkylamino, Imido, ureido, sulfamoylamino, alkoxycarbonylamino, aryloxycarbonylamino, alkoxycarbonyl, aryloxycarbonyl, heterocyclic thio, and other groups, as well as spiro compound residues, bridged hydrocarbons Compound residue and the like are also mentioned.

The alkyl group represented by R ₆ preferably has 1 to 32 carbon atoms and may be linear or branched.

The aryl group represented by R ₆ is preferably a phenyl group.

The acylamino group represented by R ₆ is
Examples thereof include an alkylcarbonylamino group and an arylcarbonylamino group.

Examples of the sulfonamide group represented by R ₆ include an alkylsulfonylamino group and an arylsulfonylamino group.

The alkyl component and aryl component in the alkylthio group and the arylthio group represented by R ₆ are the same as the above R ₃
And an alkyl group and an aryl group represented by.

The alkenyl group represented by R ₆ is preferably one having 2 to 32 carbon atoms, and the cycloalkyl group is preferably one having 3 to 12 carbon atoms, particularly 5 to 7 carbon atoms. The alkenyl group is linear or branched. But it's okay.

The cycloalkenyl group represented by R ₆ is preferably one having 3 to 12 carbon atoms, particularly 5 to 7 carbon atoms.

The sulfonyl group represented by R ₆ is an alkylsulfonyl group, an arylsulfonyl group, etc .; The sulfinyl group is an alkylsulfinyl group, an arylsulfinyl group, etc .; The phosphonyl group is an alkylphosphonyl group, an alkoxyphosphonyl group. Group, aryloxyphosphonyl group, arylphosphonyl group, etc .; acyl group, alkylcarbonyl group, arylcarbonyl group, etc .; carbamoyl group, alkylcarbamoyl group, arylcarbamoyl group, etc .; sulfamoyl group, alkylsulfayl group Moyl group, arylsulfamoyl group, etc .; Acyloxy group, alkylcarbonyloxy group, arylcarbonyloxy group, etc .; Carbamoyloxy group, alkylcarbamoyloxy group, arylcarbamoyl group An oxy group, etc .; an ureido group, an alkylureido group, an arylureido group, etc .; a sulfamoylamino group, an alkylsulfamoylamino group, an arylsulfamoylamino group, etc .; a heterocyclic group having 5 to 7 members Those which are preferable are specifically 2-
Furyl group, 2-thienyl group, 2-pyrimidinyl group, 2-benzothiazolyl group, etc .; As the heterocyclic oxy group, those having a 5- to 7-membered heterocycle are preferable, for example, 3,4,5,6-tetrahydropyranyl -2-oxy group, 1-phenyltetrazole-5-
Oxy group, etc .; As the heterocyclic thio group, a 5- to 7-membered heterocyclic thio group is preferable, and examples thereof include 2-pyridylthio group, 2-benzothiazolylthio group, 2,4-diphenoxy-1,3,5-triazole. -6-thio group; siloxy group such as trimethylsiloxy group, triethylsiloxy group, dimethylbutylsiloxy group, etc .; imide group such as succinimide group, 3-heptadecylsuccinimide group, phthalimide group, glutarimide group Etc .; as the spiro compound residue, spiro [3.
3] heptan-1-yl, etc .; bridged hydrocarbon compound residues include bicyclo [2.2.1] heptan-1-yl, tricyclo [3.
3.1.1 ³⁷ ) Decan-1-yl, 7,7-dimethyl-bicyclo (2.
2.1] Examples include heptan-1-yl and the like.

Each of the groups represented by R ₆ includes one having a substituent.

Examples of R ₇ include alkyl, substituted alkyl, aryl and substituted aryl groups. The alkyl group preferably has 1 to 32 carbon atoms and may be linear or branched. A phenyl group is preferred as the aryl group. Further, the alkyl or aryl group may have a substituent, and the substituent has the same meaning as R ₆ , but does not include a hydroxyl group, a carboxy group or a metal salt thereof.

The divalent linking group represented by L is not particularly limited, but examples thereof include an oxygen atom, acylamino, sulfonamide, sulfonyl, sulfinyl, acyl, carbamoyl, amino, ureido and acyloxy, and the like. Is an oxygen atom, acylamino, sulfonamide, acyloxy, or ureido group.

X represents a hydrogen atom or a leaving group. The leaving group is a group capable of leaving by a coupling reaction with an oxidized product of a color developing agent, and for example, a halogen atom, an alkoxy group, an aryloxy group, an acyloxy group, an arylthio group, an alkylthio group, a sulfonamide group, an acylamino group,

[0028]

[Chemical 3]

(Z is 5 to 6 selected from carbon atom, oxygen atom, nitrogen atom and sulfur atom together with nitrogen atom.
Represents the atomic group required to form a member ring. ) And the like.

Specific examples of the leaving group are shown below.

Halogen atom: atoms such as chlorine, bromine, fluorine, etc. Alkoxy group: ethoxy group, benzyloxy group, ethylcarbamoylmethoxy group, tetradecylcarbamoylmethoxy group, etc. Aryloxy group: phenoxy group, 4-methoxyphenoxy group, 4- Nitrophenoxy group, etc. Acyloxy group: Acetoxy group, myristoyloxy group, benzoyloxy group, etc. Arylthio group: Phenylthio group, 2-butoxy-5-octylphenylthio group, 2,5-dihexyloxyphenylthio group, etc. Alkylthio group: Methylthio group , Octylthio group, hexadecylthio group, benzylthio group, 2- (diethylamino)
Ethylthio group, ethoxycarbonylmethylthio group, ethoxyethylthio group, phenoxyethylthio group, etc.Sulfonamide group: methanesulfonamide group, benzenesulfonamide group, etc. Acylamino group: heptafluorobutanamide group, pentachlorophenylcarbonylamino group, etc.

[0032]

[Chemical 4]

Examples of the material represented by the following are the following:

[0034]

[Chemical 5]

The leaving group is preferably a halogen atom, and most preferably a chlorine atom.

Typical examples of the magenta coupler represented by formula (I) of the present invention are shown below, but the present invention is not limited thereto.

[0037]

[Chemical 6]

[0038]

[Chemical 7]

[0039]

[Chemical 8]

[0040]

[Chemical 9]

[0041]

[Chemical 10]

The synthesis examples of the magenta coupler represented by the general formula [I] of the present invention are shown below.

I) Synthetic route

[0044]

[Chemical 11]

II) Synthesis of Intermediate 1 To 20.1 g of m-nitrobenzaldehyde was added 12.8 g of sodium propionate and 51.9 g of propionic anhydride, and
Stir at ℃ for 8 hours.

The reaction solution is poured into ice water and the crystals are collected by filtration, dissolved in ethyl acetate, neutralized with an aqueous sodium hydrogen carbonate solution, washed with water and dried, and then the solvent is distilled off under reduced pressure. Recrystallization from ethyl acetate gave Intermediate 1: 21.5 g. (Structure is ¹
It was confirmed by 1 HNMR spectrum, IR spectrum and FD mass spectrum. ) III) Synthesis of Intermediate 4 Intermediate 1: 17.0 g of toluene 100 ml, thionyl chloride 10.
After adding 9 ml and refluxing for 5 hours, excess thionyl chloride and toluene were distilled off under reduced pressure.

This acid chloride (intermediate 2): 18.3 g and intermediate 3: 14.0 g were suspended in 300 ml of acetonitrile,
Heated to reflux.

The reaction product gradually dissolves, but crystals are precipitated again. The crystals were collected by filtration, added with toluene and heated, and then hot filtered to obtain 4: 20.6 g of an intermediate. (Structure is ¹ HNM
It was confirmed by R spectrum, IR spectrum and FD mass spectrum. ) IV) Synthesis of intermediate 5 To 17.9 g of intermediate 4: 100 ml of acetic anhydride was added and heated under reflux for 4 hours, and then excess acetic anhydride was distilled off under normal pressure (about 85 ml).
Then, the reaction solution is cooled to room temperature. Methanol 110
ml and c.HCl (10 ml) are added, the mixture is heated under reflux for 2 hours, sulfur is removed by hot filtration, and the solvent is distilled off under reduced pressure. The mixture was suspended in ethyl acetate, heated, and filtered to give Intermediate 5: 13.0 g. (The structure is ¹ H NMR spectrum, I
It was confirmed by R spectrum and FD mass spectrum. ) V) Synthesis of Intermediate 6 12.0 g of Intermediate 5 was dissolved in 200 ml of THF, 4.0 g of palladium carbon was added and hydrogenated. After completion of the reaction, palladium carbon was collected by filtration, and the solvent was distilled off under reduced pressure to obtain Intermediate 6: 9.8 g. (The structure is ¹ H NMR spectrum,
It was confirmed by IR spectrum and FD mass spectrum. ) VI) Synthesis of Intermediate 8 50 ml of ethyl acetate and 1.1 ml of triethylamine (TEA) were added to 6: 2.0 g of intermediate, and an ethyl acetate solution of 7: 2.28 g of intermediate 7 was slowly added dropwise over 20 minutes, and the mixture was kept for 3 hours. It was stirred. After completion of the reaction, the reaction mixture was neutralized, washed with water and dried, and the solvent was distilled off under reduced pressure to obtain 3.9 g of a brown oil. This is ethyl acetate:
Column chromatography was performed with n-hexane = 1: 3 to obtain 8: 3.1 g of the intermediate. (The structure was confirmed by ¹ H NMR spectrum, IR spectrum and FD mass spectrum.) VII) Synthesis of M-3 Intermediate 8: 2.9 g was dissolved in 50 ml of chloroform and cooled to 5 ° C. N-chlorosuccinimide (NCS) 0.8
Add 4 g gradually. After completion of the reaction, the product was washed with water, dried and the solvent was distilled off under reduced pressure to obtain 4.0 g of a crude product. This was subjected to column chromatography with ethyl acetate: n-hexane = 1: 4 to obtain M-3: 3.0 g. (The structure was confirmed by ¹ H NMR spectrum, IR spectrum and FD mass spectrum.) The magenta coupler used in the present invention is preferably contained in the silver halide emulsion.
For example, a conventionally known method may be followed. For example, the boiling point of tricresyl phosphate, dibutyl phthalate, etc. is 175
° C or higher high-boiling organic solvent or ethyl acetate, after each of the low-boiling solvents such as butyl propionate alone or as a mixture thereof, the magenta coupler of the present invention alone or in combination, after dissolving, It can be added to a silver halide emulsion after being mixed with an aqueous gelatin solution containing a surfactant and then emulsified with a high speed rotary mixer or a colloid mill.

The coupler of the present invention can be used usually in the range of ¹ mol of silver halide, 1 × 10 ^-3 to 1 mol, and preferably 1 × 10 ^-2 to 8 × 10 ^-1 mol.

The magenta coupler of the present invention can also be used in combination with other types of couplers.

The couplers of this invention can be used in combination with various image stabilizers. Preferable image stabilizers include phenol compounds, phenyl ether compounds, amine compounds, chelate compounds, and the like. Exemplified compounds GG described on pages 133 to 137 of JP-A No. 62-215272. -1 to GG-54, the exemplified compounds (a-1) to (a- described in JP-A-4-95952, pages 23 to 29)
8), (b-1) to (b-6), (c-1) to (c-
7), IIIa-1 to IIIa-15, IV-1 to IV-22, V-1
To V-10 and VI-1 to VI-5, JP-A-60-262159, No. 11 to
Exemplified Compounds A-1 to A-28 and 61-145 described on page 13
Exemplary compounds PH-1 to P described in No. 552, pages 8 to 10
H-29, exemplary compounds B-1 to B-21 described on pages 6 to 7 of JP-A-1-306846, and exemplary compounds I-1 to I described on pages 10 to 18 of 2-958. -13, I'-1 to I'-8, II-
1 to II-12, II'-1 to II'-21, III-8 to III-14,
IV-1 to IV-24, V-13 to V-17, No. 3-39956 No. 10-11
Exemplified compounds II-1 to II-33 described on page, JP-A 2-16
7543, compounds B-1 to B-65 described on pages 8 to 11;
Exemplified compounds (1) to (120) described on pages 4 to 7 of JP-A-63-95439 may be mentioned.

The amount of the image stabilizer used in combination with the coupler of the present invention is preferably 5 to 400 mol%, and more preferably 10 to 10 mol% based on the pyrazoloazole-based magenta coupler of the present invention. It is 250 mol.

The pyrazoloazole-based magenta coupler of the present invention and the image stabilizer are preferably used in the same layer, but the image stabilizer is used in a layer adjacent to the layer in which the coupler is present. Good.

The silver halide composition preferably used in the present invention is silver chloride, silver chlorobromide or silver chloroiodobromide. Further, it may be a combination mixture such as a mixture of silver chloride and silver bromide.

The silver halide emulsion used in the present invention contains, as silver halide, silver bromide, silver iodobromide, silver iodochloride,
Any of silver chlorobromide, silver chloroiodobromide, silver chloride, and the like used in ordinary silver halide emulsions can be used.

The silver halide grain may be a grain having a uniform silver halide composition distribution within the grain, or a core / shell grain having a different silver halide composition between the inside of the grain and the surface layer.

The silver halide grain may be a grain in which a latent image is mainly formed on the surface, or may be a grain in which a latent image is mainly formed inside the grain.

The silver halide grains may have a regular crystal form such as a cube, octahedron or tetradecahedron,
It may have an irregular crystal shape such as a sphere or a plate. In these grains, any ratio of {100} plane to {111} plane can be used. Further, it may have a composite form of these crystal forms, and particles of various crystal forms may be mixed.

The grain size of silver halide grains is preferably 0.05 to 30 μm, more preferably 0.1 to 20 μm.

The silver halide emulsion having any grain size distribution can be used. An emulsion having a wide grain size distribution (referred to as a polydisperse emulsion) may be used, or an emulsion having a narrow grain size distribution (referred to as a monodisperse emulsion) may be used alone or in combination of several kinds. Further, a polydisperse emulsion and a monodisperse emulsion may be mixed and used. The coupler used in the present invention includes a development inhibitor, a development accelerator, a bleaching accelerator, a developer, a silver halide solvent, a toning agent by coupling with a colored coupler having an effect of color correction and an oxidation product of a developing agent. Included are compounds that release photographically useful fragments such as agents, hardeners, antifoggants, antifoggants, chemical sensitizers, spectral sensitizers and desensitizers. Of these, a so-called DIR compound which releases a development inhibitor with development and improves the sharpness of images and the graininess of images may be used.

In this DIR compound, the one in which the inhibitor is directly bonded to the coupling position and the one in which the inhibitor is bonded to the coupling position via the divalent group, are A compound (referred to as a timing DIR compound) that is bound so as to release the inhibitor by an intramolecular nucleophilic reaction or an intramolecular electron transfer reaction is included. Further, as the inhibitor, one that is diffusible after withdrawal and one that is not so diffusible can be used alone or in combination depending on the application.

A colorless coupler (also referred to as a competing coupler) which undergoes a coupling reaction with an oxidized product of an aromatic primary amine developer but does not form a dye can be used in combination with the dye-forming coupler.

Examples of yellow couplers preferably used in the present invention include known acylacetanilide type couplers. Among these, benzoylacetanilide compounds and pivaloylacetanilide compounds can be advantageously used.

The cyan couplers preferably used in the present invention include phenol or naphthol couplers.

Between the emulsion layers of the light-sensitive material (the same color-sensitive layer and / or different color-sensitive layers), the oxidant of the developing agent or the electron transfer agent moves to cause color turbidity or deterioration of sharpness. Also, a color antifoggant can be used to prevent the graininess from being conspicuous.

An image stabilizer which prevents deterioration of a dye image can be used in the light-sensitive material of the present invention. Compounds which can be preferably used are those described in Item VII J of RD17643.

The hydrophilic colloid layers such as the protective layer and the intermediate layer of the light-sensitive material contain an ultraviolet ray inhibitor in order to prevent fogging due to discharge caused by charging of the light-sensitive material due to friction and the like and to prevent deterioration of the image by ultraviolet rays. You can leave.

A formalin scavenger can be used in the light-sensitive material in order to prevent deterioration of the magenta dye-forming coupler and the like due to formalin during storage of the light-sensitive material.

The present invention can be preferably applied to color negative films, color papers, color reversal films and the like.

[0070]

EXAMPLES The present invention will now be described based on examples, but the embodiments of the present invention are not limited thereto.

Example 1 On a support having polyethylene laminated 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 constitution shown in Tables 1 and 2 below. By coating on the side of the contained polyethylene layer, a multilayer silver halide color photographic light-sensitive material sample 101 was prepared.

[0072]

[Table 1]

[0073]

[Table 2]

The coating liquid was prepared as follows.

First layer coating liquid 26.7 g of yellow coupler (EY-1), 10.0 g of dye image stabilizer (ST-1), dye image stabilizer (ST-2)
Ethyl acetate (60 cc.) Was added to 6.67 g, stain inhibitor (HQ-1) (0.67 g) and high boiling organic solvent (DNP) (6.67 g) to dissolve, and this solution was added with 20% surfactant (SU-2) aqueous solution (7 cc.). 220 cc. Of 10% gelatin aqueous solution contained 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 irradiation preventing 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. Also, as a hardener, the second layer and the fourth layer
(HH-1) was added to the layer and (HH-2) was added to the seventh layer. As the coating aid, surfactants (SU-1), (S
U-3) was added to adjust the surface tension.

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

[0079]

[Chemical 12]

[0080]

[Chemical 13]

[0081]

[Chemical 14]

[0082]

[Chemical 15]

[0083]

[Chemical 16]

Blue-sensitive silver halide emulsion (Em-B) Average grain size 0.85 μm, coefficient of variation = 0.07, silver chloride content 99.5
Mol% monodisperse cubic silver chlorobromide emulsion sodium thiosulfate 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 × 10 ^-4 mol / mol AgX sensitizing dye BS-2 1 × 10 ^-4 mol / mol AgX green-sensitive silver halide emulsion (Em-G) average grain size 0.43 μm, variation coefficient = 0.08, silver chloride content 99.5 mol % Monodisperse cubic silver chlorobromide 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-sensitive silver halide emulsion (Em-R) Monodispersed cubic silver chlorobromide emulsion with average particle size 0.50 μm, coefficient of variation = 0.08, silver chloride content 99.5 mol% Sodium thiosulfate 1.8 mg / mol AgX chloroauric acid 2.0 mg / mol AgX Stabilizing agent STAB-1 6 × 10 ^-4 mol / mol AgX sensitizing dye RS-1 1 × 10 ^-4 mol / mol AgX Dynamic factor is calculated by the following equation 1.

[0085]

[Equation 1]

Here, ri represents the particle size of each particle, and ni represents the number thereof. The grain size means the diameter of a spherical silver halide grain, and the diameter of a cubic image or a grain having a shape other than spherical when the projected image is converted into a circular image having the same area.

The structural formulas of the compounds used in each monodisperse cubic emulsion are shown below.

[0088]

[Chemical 17]

Next, the third layer coupler EM-1 of Sample 101 was used.
Was replaced with an equimolar amount of the comparative coupler shown in Table 3 below or the coupler of the present invention to prepare samples 102 to 115.

The magenta coupler E used for the comparative sample
Structural formulas of M-2 and EM-3 are shown together with EM-1 described above.

The sample thus produced was wedge-exposed with green light according to a conventional method, and then treated according to the following treatment steps.

Processing process Temperature Time Color development 35.0 ± 0.3 ° C 45 seconds Bleach fixing 35.0 ± 0.5 ° C 45 seconds Stabilization 30-34 ° C 90 seconds Dry 60-80 ° C 60 seconds The composition of each processing solution is as follows. Show.

The replenishing amount of each processing solution is 80 cc. Per 1 m ^{2 of} silver halide color photographic light-sensitive material.

Color developer tank solution Replenisher Pure water 800cc. 800cc. Triethanolamine 10g 18g N, N-diethylhydroxylamine 5g 9g Potassium chloride 2.4g 1-Hydroxyethylidene-1,1-diphosphonic acid 1.0g 1.8g N -Ethyl-N-β-methanesulfonamidoethyl-3-methyl-4-aminoaniline sulfate 5.4g 8.2g Optical brightener (4,4'-diaminostilbenesulfonic acid derivative) 1.0g 1.8g Potassium carbonate 27g 27g Add water to make the total volume 1000 cc.
Is adjusted to 10.10 and the pH of the replenisher is adjusted to 10.60.

Bleach-fixing solution (tank solution and replenisher are the same) Ethylenediaminetetraacetic acid ammonium ferric dihydrate 60g Ethylenediaminetetraacetic acid 3g Ammonium thiosulfate (70% aqueous solution) 100cc. Ammonium sulfite (40% aqueous solution) 27.5cc. Water To 1000 cc. And adjust the pH to 5.7 with potassium carbonate or glacial acetic acid.

Stabilizing solution (tank solution and replenisher 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 2.0 g ethylenediamine Tetraacetic acid 1.0 g Ammonium hydroxide (20% aqueous solution) 3.0 g Optical brightener (4,4'-diaminostilbene sulfonic acid derivative) 1.5 g Add water to bring the total volume to 1000 cc. And adjust the pH with sulfuric acid or potassium hydroxide. Adjust to 7.0.

The following evaluations were 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 of 70,000 lux for 320 hours, and the residual ratio (%) of the dye image at the initial density of 1.0 was determined.

<Λmax> The maximum absorption wavelength was measured.

<Abs 600> Absorbance of the wedge at 600 nm (the absorbance at λmax is 1.0
And) was measured.

The results are shown in Tables 3 and 4.

[0103]

[Table 3]

As is clear from Table 3, the samples 104 to 115 using the magenta coupler of the present invention are superior in both color development and light resistance to the comparative samples 101 to 103.

[0105]

[Table 4]

As is clear from Table 4, the samples 104 to 115 using the magenta coupler of the present invention have a reduced absorbance at 600 nm (sharp absorption) as compared with the comparative samples 101 to 103, and color reproduction. The nature is improving.

[0107]

According to the present invention, firstly, it is possible to provide a silver halide color photographic light-sensitive material in which the light resistance of a dye image is improved and the image storability is excellent. Secondly, a silver halide color photographic light-sensitive material excellent in color reproducibility can be provided.

Claims (1)

[Claims] 1. A silver halide color photographic light-sensitive material comprising at least one magenta coupler represented by the following general formula [I]. [Chemical 1] [In the formula, R ₁ represents a tertiary alkyl group, and R ₂ , R ₄ , R ₅
Represents a hydrogen atom or an alkyl group, and R ₃ represents an alkyl group. R ₆ represents a substituent, R ₇ is an alkyl group,
It represents a substituted alkyl group, an aryl group or a substituted aryl group, and the substituent does not include a hydroxyl group, a carboxy group or a metal salt thereof. L represents a divalent linking group, 1 represents an integer of 1 to 10, m represents an integer of 0 to 5, and n represents an integer of 0 to 5. X represents a hydrogen atom or a group which is released by a reaction with an oxidized product of a color developing agent. ]