JPH04133053A - Silver halide color photographic sensitive material - Google Patents

Abstract

PURPOSE:To provide the above-mentioned material having higher color developability and higher light resistance by using a specific pyrazolotriazole magenta coupler. CONSTITUTION:Emulsion layers contg. the pyrazolotriazole magenta coupler which is substd. with an annular secondary amine in the coupling position and is expressed by general formula (I) or (II) are applied on a paper base laminated with polyethylene on both surface and further, an intermediate layer contg. a UV absorbent and a gelatin-contg. protective layer are applied thereon successively from the base side. This material is passed through an optical wedge and is subjected to color developing by a prescribed processing liquid, bleach fixing, washing and drying after exposing. The coupler itself acts as an antioxidizing of the azomethine dye formed by the coupler itself and, therefore, the deterioration in the light resistance is obviated and the high light resistance even in the low density part of a high residual coupler ration is attained.

Description

DETAILED DESCRIPTION OF THE INVENTION [Industrial Application Field] The present invention relates to a silver halide color photographic light-sensitive material containing a magenta coupler that forms a magenta dye image with high color development and improved light fastness. More specifically, the present invention relates to a silver halide color photographic light-sensitive material containing a pyrazolotriazole magenta coupler whose coupling position is substituted with a cyclic secondary amine.

Background of the Invention] Usually, in silver halide color photographic materials, exposed silver halide grains are reduced with an aromatic primary amine color developing agent, and the oxidized product of the color developing agent produced at this time is reduced. Each dye image can be obtained by coupling the colorant with couplers that form yellow, magenta, and cyan dyes.

Pyrazolone couplers have conventionally been used in practice to form the magenta dye, but these have the disadvantages of having undesirable side absorption and poor storage stability.

In order to improve the above drawbacks, various [H-pyrazolo[3,2-C]-5-h lyazole magenta couplers have been proposed. These include, for example, US Pat.
No. 25.087, British Patent No. 1,252.418, No. 1
, 334.515. All of the compounds described in these patents are superior to pyrazolone-based magenta couplers in terms of side absorption, and show little improvement in color development and light resistance of images. Research Disc+ -(Research Disc
The compound described in No. 12443 cannot be put to practical use at all in terms of color development. Japanese Patent Publication No. 58-42045
Although the IH-pyrazolo[3,2C]-5-) lyazole type macenta coupler described in the above issue has been significantly improved in terms of formalin resistance and color development, there has been little improvement in light resistance. .

Also, JP-A No. 59-99437, No. 59-125732
The couplers described in this issue also show continued improvement in terms of the light fastness of dye images. That is, in the latter case, the light resistance of the image is merely improved by the additive used in combination, and in the former case, the light resistance of the coupler of Compound Example 19 described in the specification is slightly improved, but it cannot be said to be sufficient. .

All of the pyrazolotriazole magenta couplers that have been put into practical use have the coupling position substituted with a chlorine atom. Although this 2-equivalent pyrazolotriazole coupler substituted with chlorine atoms does improve color development, the coupler remaining after color development greatly deteriorates the light resistance of magenta dye images, especially when the proportion of remaining coupler is large. It was found that the effect becomes more pronounced in low concentration areas.

As a 2-equivalent pyrazolotriazole magenta coupler having a leaving group other than a halogen atom, JP-A-59-994
37, 2-equivalent pyrazolotriazole magenta couplers in which the coupling position is substituted with nitrogen as described in JP-A-81-140241, JP-A-81-53644, JP-A-81-65243, JP-A-81-158048, 61
-156049, 81-180745, 81-
2-equivalent pyrazolotriazole magenta coupler in which the coupling position is substituted with oxygen as described in No. 182045 and No. 61177456, JP-A-61-15964
No. 6, No. 61-159647, No. 61-165757
No. 61-1898413, No. 62-56963 in which the coupling position is substituted with sulfur.
Equivalent pyrazolotriazole magenta couplers are known, but none of these have sufficient color development.
The light fastness of the dye image is also not at a satisfactory level.

The inventors of the present invention have carried out intensive research aimed at improving the above points, and as a result, they have discovered a pyrazolotriazole-based magenta coupler that has excellent light resistance for magenta dye images and also exhibits high color development. It was.

[Object of the Invention] Therefore, an object of the present invention is to provide a silver halide color photographic light-sensitive material in which a magenta dye image has good light fastness and high color development.

[Structure of the Invention] The object of the present invention is to provide a silver halide color photographic material having at least one silver halide emulsion layer on a support.
Or, it can be achieved by a silver halide color photographic light-sensitive material characterized by containing at least one magenta coupler represented by the general formula [II].

General formula [Il -Y General formula [I[] , -Y [wherein, R1 and R2 represent substituents, and Y is necessary to form a 5- to 7-membered non-aromatic heterocycle together with nitrogen] represents a group of nonmetallic atoms. ] Next, the present invention will be explained in detail.

First, the magenta couplers (hereinafter referred to as the couplers of the present invention) represented by the general formulas [Il and [II]] will be explained.

In general formula [Il and general formula [II], R1 and R
The substituent represented by 2 is not particularly limited, and typically includes alkyl, aryl, anilino, acylamino,
Sulfonamide, alkylthio, arylthio, alkenyl, cycloalkyl, heterocycle, etc., or other groups! ＼Rogen atoms and cycloalkenyl, alkynyl, sulfonyl, sulfinyl, sulfonyloquine, phosphonyl, acyl, carbamoyl, sulfamoyl, cyano, alkoxy, aryloxy, heterocyclicoxy, siloxy, acyloxy, carbamoyloxy, amino, alkylamino, imide, Examples include ureido, sulfamoylamino, alkoxycarbonylamino, aryloxycarbonylamino, alkoxycarbonyl, aryloxycarbonyl, heterocyclic thio, thioureido, carboxyl, hydroxy, mercapto, nitro, and sulfo groups.

The alkyl group is preferably one having 1 to 32 carbon atoms, and may be linear or branched.

Examples of the aryl group include a phenyl group and a naphthyl group.

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

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

Examples of the alkyl component and aryl component in the alkylthio group and arylthio group include the aforementioned alkyl groups and aryl groups.

The alkenyl group preferably has 2 to 32 carbon atoms, and the cycloalkyl group preferably has 3 to 12 carbon atoms, particularly 5 to 7 carbon atoms, and the alkenyl group may be linear or branched.

The cycloalkenyl group has 3 to 12 carbon atoms, especially 5
-7 is preferred.

Sulfonyl groups include alkylsulfonyl groups, arylsulfonyl groups, etc. Sulfinyl groups include alkylsulfinyl groups, arylsulfinyl groups, etc. Phosphonyl groups include alkylphosphonyl groups, alkoxyphosphonyl groups, aryloquinphosphonyl groups, and arylphosphonyl groups. Acyl groups include arylcarbonyl groups, arylcarbonyl groups, etc.; carbamoyl groups include alkylcarbamoyl groups, arylcarbamoyl groups, and sulfamoyl groups include alkylsulfamoyl groups;
Acyloxy groups such as arylsulfamoyl groups include alkylcarbonyloxy groups,
Arylcarbonyloxy group, etc.

Examples of sulfonyloxy groups include alkylsulfonyloxy groups and arylsulfonyloxy groups; examples of carbamoyluoquine groups include alkylcarbamoyloxy and arylcarbamoyluoquine groups; and ureido groups include sulfamoylamino groups such as alkylureido and arylureido groups. Examples of the heterocyclic group include an alkylsulfamoylamino group, an arylsulfamoylamino group, and a 5- to 7-membered heterocyclic group, specifically a 2-furyl group, a 2-thienyl group, a 2-pyrimidinyl group, 2-Benzothiazolyl group, 1-pyrrolyl group, 1-tetrazolyl group, etc.: The heterocyclic oxy group preferably has a 5- to 7-membered heterocycle, such as 3,4,5.6-titrahydropyranyl-2- Oxy group, 1-phenyltetrazole-5-
Oxy group, etc.; The heterocyclic thio group is preferably a 5- to 7-membered heterocyclic thio group, such as 2-pyridylthio group, 2-benzothiazolylthio group, 2,4-diphenoxy-1,3,5-triazole- 6-thio group, etc.; examples of siloquine group include trimethylsiloquine group, trimethylsiloquine group, dimethylbutylsiloxy group, etc.; examples of imide group include succinimide group, 3-heptadecylsuccinimide group, phthalimide group, cultarimide group The above-mentioned groups may further have a substituent such as a long-chain hydrocarbon group or a diffusion-resistant group such as a polymer residue.

As a 5- to 7-membered non-aromatic heterocyclic group represented by -NY in the general formula [Ill], R3 represents a substituent, R4 is a hydrogen atom, an alkyl group , represents an aryl group, an acyl group, a sulfonyl group, or a coupler residue, 1, j2k and m represent an integer from 0 to 8, and g represents an integer from 0 to 2. ] The substituent represented by R1 above has the same meaning as R4 and R2 described above, and preferable substituents include groups such as alkyl, aryl, halogen atom, carboxyl, alkoxycarbonyl, and aryloxycarbonyl. .

The alkyl group represented by R4 preferably has 32 to 32 carbon atoms, and may be linear or branched.

Examples of the aryl group include a phenyl group and a naphthyl group.

Examples of the acyl group include an acetyl group, a propionyl group, a pivaloyl group, a benzoyl group, and a chloroacetyl group.

Examples of the sulfonyl group include a methanesulfonyl group, a butanesulfonyl group, a t-butylsulfonyl group, and a benzenesulfonyl group.

Specific examples of the blank coupler residues below include (R1 and R7 are synonymous with R1 and R2 in general formula [1] and general formula [■).

In general formula [I] and general formula [n], the group is
Specifically, the following can be mentioned.

R4 above Hamae Jki R4 is synonymous with these complex The ring group may further have a substituent.

Among these, the preferred one Then, The following There are several examples.

These heterocyclic groups may have a substituent.

Specific examples of the coupler of the present invention are shown below, but the coupler of the present invention is not limited to these.゜10゜11゜C0C)13 12゜13゜6F113 CaL7(t) 14゜15゜H3 16゜20゜21゜23゜2H5 H3 CaHI 7 (1) CI(3 (CH2C CH3CN and.

Synthesis Example 1 Synthetic route for synthesis of Exemplified Compound 12> [(Intermediate 1 25° Intermediate 2 x/y = 45155 (Ratio of W) Exemplified Compound 12 <Synthesis of Intermediate 2> Intermediate 1 30.0sr and acetic acid After adding 300 ml of ethyl and stirring at room temperature, 12.21 r of N-bromosuccinimide (N B S ) was gradually added over about 30 minutes. After stirring for another 30 minutes, 0.4 g of N-bromosuccinimide was added. The reaction solution was stirred for 1 hour to complete the reaction.The reaction solution was washed twice with 300 ml of water and further dried over anhydrous magnesium sulfate, and the solvent ethyl acetate was distilled off under reduced pressure to obtain a pale yellow color. The oil was recrystallized from 3 times the amount of methanol to obtain Intermediate 23L, 2. as pale yellow crystals.

(It was confirmed to be Intermediate 2 by HNMR, FD mass spectrum, and IR spectrum.) Exemplified Compound 1
Synthesis of 2> Dissolve 26.0 g of the intermediate in 50 ml of sulfolane, add 20 ml of pyrrolidine, and heat at 90°C under a nitrogen stream.
10 (heated and stirred at 1'C for 2 hours. 100 ml of ethyl acetate was added to the reaction solution, washed three times with 50 ml of water, and then dried over anhydrous sodium sulfate.

The solvent ethyl acetate was distilled off under reduced pressure, and the resulting brown surface was purified by silica gel column chromatography, and further recrystallized with a 2/1 mixed solvent of ethyl acetate/hexane to give white crystals of Exemplified Compound 121. .2g was obtained.

(It was confirmed to be Exemplified Compound 12 by 'HNMR, FD mass spectrum, and IR spectrum.) Synthesis Example 2 Synthesis of Exemplified Compound 13 <Synthesis Route> Intermediate 2 Exemplified Compound 13 260 g of the above intermediate was dissolved in 30 ml of sulfolane. , further added 20 ml of morpholine, and heated at 120 mL under a nitrogen stream.
The mixture was heated and stirred at ℃ for 5 hours. Add 150% ethyl acetate to the reaction solution.
ml and washed with 200 ml of water, followed by washing three times with 200 ml of saline. After drying over anhydrous magnesium sulfate, ethyl acetate was distilled off under reduced pressure, and the resulting brown solid was purified by column chromatography. Further, 132.7 g of the exemplified compound as white crystals was obtained by recrystallizing with a mixed solvent of ethyl acetate/hexane = 3/1.

(It was confirmed to be Exemplified Compound 13 by HNMR, FD mass spectrum, and IR spectrum.) Synthesis Example 3 Synthesis of Exemplified Compound 14 <Synthesis Route> I (Intermediate 1 Intermediate 3 Intermediate 4 Intermediate 3 Synthesis> Intermediate 1 10.0g, acetic acid 120ml, concentrated hydrochloric acid 2
ml and stirred under water cooling to 10°C. An aqueous solution of 1.6 g of sodium nitrite (10 m of water)
1) was added dropwise and stirred for an hour. After adding Hml of saturated brine and neutralizing with sodium hydrogen carbonate, the precipitated solid was collected by filtration, and this solid was further recrystallized with acetonitrile to obtain 310.1 g of a white crystal intermediate.

(It was confirmed that it was Intermediate 3 by 'HNMRFD mass spectrum and IR spectrum.) <Synthesis of Intermediate 4> To 38.0 g of Intermediate, 1.20 ml of water and 255 g of sodium hydrosulfide were added, and the mixture was stirred at room temperature. :.

16 ml of pyridine was added dropwise thereto over about 30 minutes, and the mixture was further stirred at room temperature for 2 hours. 350 ml of saturated brine was added, the precipitated solid was collected by filtration, and this solid was further recrystallized with acetonitrile to obtain 449 g of an intermediate in the form of pale orange crystals.

(It was confirmed that it was Intermediate 4 by 'HNMRFD mass spectrum and IR spectrum.)
Synthesis> After heating and dissolving 450 g of the intermediate in 20 ml of n-butanol, 1.35 g of divinylsulfone was added, and the mixture was heated under reflux for 3 hours. After n-butanol was distilled off under reduced pressure, 141.7 g of the exemplified compound as white crystals was obtained by recrystallizing with Metazuru.

(It was confirmed to be Exemplified Compound 14 by 'HNMR, FD mass spectrum, and IR spectrum.) As described above, the coupler of the present invention is a pyrazolotriazole magenta compound substituted with a cyclic secondary amine at the coupling position. It is a coupler.

The reason why the light resistance is greatly improved when using this coupler is that the conventional pyrazolotriazole magenta coupler in which the coupling position is substituted with a chlorine atom, or the light resistance deteriorates due to the azomethine dye produced by color development processing. In contrast, the coupler of the present invention acts as an antioxidant for the azomethine dye that is produced by itself, and can achieve high light resistance even in low-concentration areas with a high proportion of residual coupler. can.

The techniques used for conventional couplers are similarly applicable to the couplers of the present invention.

The coupler of the present invention can be incorporated into a silver halide solvent layer in a photographic constituent layer using a conventionally known method, for example, using a high boiling point solvent such as dibutyl phthalate, tricresyl phosphate, dinonylphenol, butyl acetate, propionate, etc. After the coupler of the present invention is dissolved in a low boiling point solvent such as ethyl chloride alone or in a mixture thereof, it is mixed with an aqueous gelatin solution containing a surfactant, and then subjected to a high-speed rotary mixer, a colloid mill, or an ultrasonic disperser. It is possible to use a method in which the emulsion is emulsified and dispersed and then directly added to the emulsion, or the emulsion dispersion is set, cut into pieces, washed with water, and then added to the emulsion.

The amount of the coupler of the present invention added is usually in the range of i.o.times.10@-3 mol to 1.0 mol, preferably from 5.times.1Q-3 to 8.times.10@-' mole per mole of silver halide.

The couplers of the present invention may be used alone or in combination of two or more.

Furthermore, a magenta coupler other than the coupler of the present invention may be used in combination.

The silver halide emulsion used in the light-sensitive material of the present invention can be chemically sensitized by conventional methods, or can be optically sensitized to a desired wavelength range using a sensitizing dye.

Antifoggants, stabilizers, etc. can be added to the silver halide emulsion. It is advantageous to use ceratin as the inter for the emulsion.

The emulsion layer and other hydrophilic colloid layers may be hardened or may contain a plasticizer or a dispersion (latefx) of a water-insoluble or sparingly soluble synthetic polymer.

In addition to the coupler of the present invention, other couplers may be used in the emulsion layer of the light-sensitive material of the present invention.

Furthermore, by coupling with a colored coupler having a color correction effect, a competitive coupler, and an oxidized form of a developing agent, a development accelerator, a bleach accelerator, a developer, a silver halide solvent,
Compounds that release photographically useful fragments such as toning agents, hardeners, fogging agents, antifoggants, chemical sensitizers, spectral sensitizers and desensitizers can be used.

The photosensitive material of the present invention can further be provided with auxiliary layers such as a filter layer, an antihalation layer, and an antiirradiation layer. These layers and/or the emulsion layer may contain dyes that are leached from the light-sensitive material or bleached during the development process.

The photosensitive material of the present invention includes a formalin scavenger-1 optical brightener, a matting agent, a lubricant, an image stabilizer, a surfactant,
Color antifoggants, development accelerators, development retardants and bleach accelerators can be added.

As a support, paper laminated with polyethylene, etc.
Polyethylene terephthalate film, baryta paper, cellulose triacetate, etc. can be used.

To obtain a dye image using a photosensitive material using the coupler of the present invention, commonly known color photographic processing can be performed after exposure.

[Example] Next, the present invention will be described in more detail with reference to Examples, but the present invention is not limited thereto.

Example 1 On a paper support laminated on both sides with polyethylene, the following layers were sequentially coated from the support side.

1st layer: emulsion layer macenta coupler M-1 3.7 mg/too
cd, silver chlorobromide emulsion (containing 85 mol% silver bromide) converted to silver is 3.5 mg/100 c4. Trioctyl phosphate was applied at a coating amount of 3.5 mg/100 c4 and seratin was applied at a coating amount of 12.0 mg/100 co.

Second layer, intermediate layer (ultraviolet absorber-containing layer) 2-(2-hydroxy-3-5ec-butyl-5-
4.8 m of t-butylphenyl)hencytriazole
g/100 an! , nobutyl phthalate 5.0
mg/1.00 c- and 12.0 mg of Seratin
The coating was applied so that the coating amount was /1 ooc♂.

Third layer/protective layer Ceratin was coated at a coating amount of 80 ♂/1o Oc♂.

The sample obtained as described above was designated as Sample 1.

Sample 2 was prepared in the same manner as Sample 1, except that the magenta coupler ~1-1 in Sample 1 was replaced with Comparative Coupler 1 in an equimolar amount.

Further, Sample 3 was prepared in the same manner as Sample 1 except that the magenta coupler M-1 in Sample 1 was replaced with Comparative Coupler 2 having an equimolar amount.

In addition, Samples 4, 5, 6 and 7 were prepared in the same manner as Sample 1 except that the magenta coupler M-1 of Sample 1 was replaced with couplers 12, 13, 14 and 15 of the present invention in equimolar amounts. did.

Below are the margins ~ 1-1 Comparative coupler 1 S After exposure through an optical wedge, processing was carried out in the following steps.

[Processing process] Processing temperature Processing time Color development 33°C 3 minutes 30 seconds Bleach fixing
Wash with water at 33℃ for 1 minute and 30 seconds 3
Dry for 3 minutes at 3℃ 50-80℃
The composition of each 2-minute treatment solution is as follows.

[Color developer] Benzyl alcohol 12ml Diethylene glycol 10ml Potassium carbonate 25, Sodium bromide
0.6g anhydrous sodium sulfite
2.0g Hydroxyamine sulfate 2.5g N-ethyl-N-β-methanesulfonamidoethyl-3-methyl-4-aminoaniline sulfate 4.5g Add water to make 1g, pH 10 with sodium hydroxide, Adjust to 2.

[Bleach-fix solution] Ammonium thiosulfate 120g Sodium metabisulfite 15g Anhydrous sodium sulfite 3g Ethylenecyaminetetraacetic acid ferric ammonium salt 65g Water was added to make 1g, and the pH was adjusted to 6.7 to 6.8.

The density of the samples 1 to 7 treated above was measured using a densitometer (model KD-7R manufactured by Konica Corporation), and the color development sensitivity s
o = 0.3 (relative value of sensitivity expressed as the reciprocal of the exposure amount that gives a density of 0.3 (specimen 1 is 100)), gradation γ
, the maximum concentration D max was calculated.

Furthermore, each of the above-mentioned treated samples was irradiated with 70,000 liters of light using a Socx xenon phase meter for 100 hours to examine the light fastness of the dye image. However, the evaluation of each item of light resistance of the dye image is as follows.

[Residual rate D-0,5] Percentage of dye remaining after light resistance test for initial density 0,5 [Residual rate D-1,0] Percentage of dye remaining after light resistance test for initial density 1.0 As is clear from Table 1 Sample 4.5 using the coupler of the present invention.
Samples 6 and 7 exhibited almost the same color development as comparative sample 1 using coupler N1-1 in which a chlorine atom was substituted at the coupling link position, and the light resistance was significantly improved compared to sample 1.
This effect is particularly noticeable in areas with low color development.

In comparison, Sample 2 using Comparative Coupler 1 had poor color development, and its light fastness could not even be evaluated satisfactorily. In No. 43, when a color development process was performed, the sample became a blue to bluish-purple color image instead of a magenta color image.

Example 2 85 mol of silver bromide used in Samples 1 to 7 of Example 1? Sample 20 was prepared in the same manner as Samples 1 to 7 except that the silver chlorobromide emulsion containing 6-containing silver chloride was replaced with a silver chlorobromide emulsion containing 995 mol% of silver chloride.
1 to 207 were created.

After exposing the sample obtained above through an optical wedge according to a conventional method,
The treatment was carried out in the following steps.

[Processing process] Color development, bleaching, fixing, stabilization, drying, drying, color developer, pure water, triethanolamine, N,N-diethylhydroxyamine, sodium bromide, potassium chloride, potassium sulfite, 1-hydroxyethylidene, time ℃ 45 seconds ℃ 45 seconds Air drying for 90 seconds Temperature 35.0±03 35.0±0.5 30-34°C Room temperature (25°C) 800 ml 0g g 02g g 0.3g 1.1-diphosphonic acid 1.0g Ethylenediaminetetraacetic acid [Og Catechol-35-disulfone Acid disodium salt 10g N-ethyl-N-β-methanesulfonamidoethyl-3-methyl-4-aminoaniline sulfate 4.5g optical brightener (4-4'-noaminostilhenesulfonic acid derivative) 1. Add 0g of potassium carbonate and 27g of water to bring the total amount to 1g, and adjust the pH to 10.10.

Bleach-fix solution Ferric ammonium dihydrate ethylenediaminetetraacetic acid 60g Ethylenediaminetetraacetic acid 3g Ammonium thiosulfate (70% aqueous solution) 100ml Ammonium sulfite (40% aqueous solution > 27.5+++1 Add water to 1
g, and adjust the pH to 8.2 with potassium carbonate or glacial acetic acid.

Stabilizing liquid 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 ethylenediaminetetraacetic acid 1.0 g ammonium hydroxide (20 % aqueous solution) 30g ammonium sulfite
3.0g Fluorescent brightener (4,4'-diaminostilbennephosphonic acid derivative) 15g Add water to make 1g, add sulfuric acid or potassium hydroxide to pH 7
, adjust to 0.

Example 1 for samples 201-207 treated above
A similar evaluation was made. The results are shown in Table 2.

Below is a sample 204 using the coupler of the present invention in the same way as in Example 1.
It was found that samples 207 to 207 exhibited almost the same color development as comparative sample 201, and the light resistance was significantly improved compared to sample 201. Sample 202 did not develop sufficient color, similar to sample 42 in the example, and sample 203 had a blue to bluish-purple color image.

Example 3 On a paper support double-sided laminated with polyethylene, the following layers were sequentially coated from the support side to prepare a multicolor silver halide photographic light-sensitive material, and Sample 301 was obtained.

1st layer: Blue-sensitive silver halide emulsion layer α-pivaloyl-α-(2,4
,-dioxo-1-benzylimidazolidin-3-yl)-2-chloro-5-[γ-(2°4-di-t-amylphenoquine)butyramide]acetanilide at 6.8
mg/too c4, blue sensitive silver chloride bromide emulsion (silver chloride 9
95 mol%) converted to silver is 3.2 a+g /
100 cd, 3.5 mg/1 dibutyl phthalate
0Qcj and gelatin at 13.5tn1z/Ioo
The coating was applied so as to have a coating amount of cd.

2nd layer Intermediate layer 2.5-di-t-octylhydroquinone 0.5m
g/100cd, 0.5mg dibutyl phthalate
/100c and Seratin 9,0mg/100
It was coated so that it was cm.

3rd layer, green-sensitive silver halide emulsion layer magenta coupler M-2 at 3.7 mg/100c4;
Green-sensitive silver chlorobromide emulsion (containing 995 mol% silver chloride) in terms of silver: 2.5 mg/100 cJ, dibutyl phthalate: 3.0 mg/10ocd, dye image stabilizer A
2,5 tng/100cJ and gelatin at 12.
The coating was applied so that offlg/1.0OcJ.

4th layer Intermediate layer 0.6 m of 2-(2-hydroxy-35-sheet-t-butylphenyl)benzotriazole as an ultraviolet absorber
g / 100 cd, dibutyl phthalate 6゜n+
g/1ooc, 0.5 mg/100 cd of 2,5-di-t-octihydroquinone and 12. g/100 cd of gelatin.
It was coated so that it was 0 mg/l (10 cm).

Fifth layer, red-sensitive silver halide emulsion layer containing 2-Ea-C,2,4- as a cyan coupler.
Pentylphenol)butanamide]-46cyclo-5-ethylphenol 4.2a+g/l 00 cd
, red-sensitive silver chlorobromide emulsion (containing 99.5 mol% silver chloride) in terms of silver: 3.0 mg/100cd, tricresyl phosphate at 3.5 mg/100 c-, and gelatin at [1.5 mg/1] It was coated so that it became .00 cd.

6th layer: Protective layer Gelatin was coated at a concentration of 8.0 mg/10Oc-.

Samples 302 to 308 were prepared in the same manner as Sample 301, except that the magenta coupler used in the third layer of Sample 301 was replaced with a coupler of the present invention shown in Table 3 having an equimolar amount.

The sample obtained above was exposed to green light through an optical wedge in a conventional manner, and then treated in the same manner as in Example 2.

Each treated sample was evaluated in the same manner as in Example 1. (
The light resistance evaluation was carried out after 400 hours of irradiation using a 70,000 lux xenon phatemeter. The results are shown in Table 3.

Color Image Stabilizer A ~1 As is clear from Table 3 below, Samples 302 to 308 using the couplers of the present invention exhibited almost the same coloring properties as Comparative Sample 301, and also had very good light resistance. It shows.

[Effects of the Invention] According to the silver halide photographic material containing the magenta coupler of the present invention, it is possible to achieve both high color development and high light fastness.

Claims (2)

[Claims] (1) In a silver halide color photographic light-sensitive material having at least one silver halide emulsion layer on a support, magenta represented by the general formula [I] or the general formula [II] is contained in the silver halide emulsion layer. A silver halide color photographic material containing at least one coupler. General formula [I] ▲There are mathematical formulas, chemical formulas, tables, etc.▼ General formula [II] ▲There are mathematical formulas, chemical formulas, tables, etc.▼ [In the formula, R_1 and R_2 represent substituents, and Y is 5 to 7 along with nitrogen Represents a group of nonmetallic atoms necessary to form a non-aromatic heterocyclic ring. ] (2) In general formula [I] and general formula [II], a 5- to 7-membered non-aromatic heterocyclic group represented by ▲ has a mathematical formula, chemical formula, table, etc. There is▼,
▲There are mathematical formulas, chemical formulas, tables, etc.▼, ▲There are mathematical formulas, chemical formulas, tables, etc.▼, ▲Mathematical formulas, chemical formulas,
There are tables, etc.▼ [In the formula, R_3 represents a substituent, R_4 represents a hydrogen atom, an alkyl group, an aryl group, an acyl group, a sulfonyl group, or a coupler residue, and i, j, k, and m are 0 to 8. , and l represents an integer from 0 to 2. ] The silver halide color photographic light-sensitive material according to claim (1).