JPS6254258A - Silver halide photographic sensitive material - Google Patents

Abstract

PURPOSE:To obtain the titled material having an excellent coloring property and a sufficient max. concentration and an excellent durability of a colored image by incorporating a specific coupler to the titled material. CONSTITUTION:The titled material contains the coupler shown by the formula wherein R2 is an alkyl, an aryl or a heterocyclic ring, Z is a hydrogen atom, a halogen atom or a group capable of substituting a benzene ring, X and Y are each a hydrogen atom or a group capable of substituting a benzene ring, B is s group capable of substituting a benzene ring, (n) is 0 or 1, R1 is an alkyl group such as a methyl, an ethyl, an isoprophyl, a tertiary butyl or a dodecyl group etc. the alkyl shown by R1 may be further substd. The substituent comprises for examples, a halogen atom, an aryl, an aryloxy, an alkylsulfonyl, an acrylamino, an alkoxy and a hydroxy groups etc.

Description

[Detailed Description of the Invention] [Industrial Application Field] The present invention relates to a silver halide photographic light-sensitive material, and more specifically, a silver halide photographic material that has excellent color development, no dye staining, excellent light resistance, and is inexpensive and easily synthesized. The present invention relates to a silver halide photographic light-sensitive material using an active site-substituted yellow coupler that can be used.

[Background of the Invention] Silver halide photographic materials have high photosensitivity and excellent image properties and have been widely used for a long time.However, due to the large amount of silver used, there has been a recent shortage of silver resources. The resulting rise in raw material costs has had a serious impact, and there is a demand for the development of technology that can save the amount of silver.

As one technique to meet this demand, silver-saving silver halide photographic materials have been proposed.

For example, as described in Japanese Patent Publication No. 49-13576, an M substituent was introduced into the active site of a color coupler. In contrast, a technique using a so-called 2-arm m-type coupler, which requires two atoms of silver, is known. According to this method, it is theoretically possible to reduce the amount of silver m used to one half of that when using a conventional so-called 4-hole type coupler, but in reality, compared to the 4-hole type coupler, it is possible to reduce the amount of silver m used. Due to the high utilization efficiency of silver, it is possible to reduce the amount of silver to less than 1/2, so in recent years, this 2-equal m-type coupler has been widely used.

On the other hand, after imagewise exposure of a silver halide photographic light-sensitive material containing a color coupler, regardless of whether it is a 2-way type or a 4-way type, it is developed with a color developing solution containing an aromatic primary amine developing agent. Methods for forming dye images are already known.

Among the color couplers used, yellow couplers generally have active methylene groups that serve to couple with the oxidation products of aromatic primary amine developing agents to form yellow dyes.

The most practically used yellow couplers are α-azila te1 to anilide j (T's b C), and among them, α-viva[1 yl- 2-chlorine 1-anilide-type yellow coupler (J,
Compared to other yellow couplers with the same structure, it has excellent C preservation properties, especially in terms of light resistance. However, when used as a 4-force type coupler, the color development is weak and it is not practical, so the 2-force type coupler mentioned above is used.
The technology was developed and it has been put into practical use as a coupler to this day.

On the other hand, in terms of development processing, benzyl alcohol has been added to the conventional color developer solution to increase the color development efficiency in the photosensitive material, but benzyl alcohol has environmental pollution problems such as B and O.

[], which has problems such as increasing the (biological oxygen demand) value. Therefore, it is desired to develop a yellow coupler that has sufficient color development even when the amount of benzyl alcohol added in the color development process is reduced.

In the case of a color development process in which the amount of benzyl alcohol added is avoided, α-Viva [1yl-2-ri■ Corua I? 1~
Almost all of the anilide-type 2-equivalent yellow couplers have poor color development, and in many cases even slight changes in the high boiling point solvent have a large effect on photographic properties. 5 of them
When an alkoxycarbonyl group, an unsubstituted alkylsulfonamide group, or an arylsulfonamide group is introduced into the ballast component at the position, the color development (maximum density) is improved, although it cannot be said to be sufficient. but,
Problems associated with this include an increase in fog density and color staining, and further problems such as significantly inferior storage stability (especially light resistance) when an alkoxycarbonyl group or an N-unsubstituted alkylsulfonamide group or arylsulfonamide group is introduced, respectively. Alternatively, there are problems such as the raw materials are expensive, unsuitable for industrial mass synthesis, or difficult to purify.

[Objective of the Invention] The present invention solves the above-mentioned problems of the conventional art. An object of the present invention is to provide an excellent silver oxide photographic sensitizer 1.

Structure of the Invention] The above object of the present invention is achieved by providing a silver halide photographic photosensitive material containing a coupler represented by the following general formula [1].

General formula [I] (wherein R1 represents an alkyl group, a Schif[1al:1nyl group, or an aryl group, I-N- or -NR3
R4 -Co-J- [R3 represents an alkyl group, aryl group or heterocyclic group, R4 represents a hydrogen atom or a group having the same meaning as R3 above, J represents a divalent bonding group and represents 1゜co ,
R2 represents an alkyl group, an aryl group, or a heterocyclic group, Z represents a hydrogen atom, a halogen atom, or a pen (represents a group that can be substituted on a non-ring), and X and Y represent a hydrogen atom or a group that can be substituted on a benzene ring. , [3 represents a 2r group that can be substituted on the benzene ring, and 0 represents O or 1. ) [Specific structure of the invention] In the general formula [R1, R1'r is represented by Al4
Examples of the -ru group include a methyl group, a delta group, an isopropyl group, a [-butyl group, and a dodecyl M group. These alkyl groups represented by R1 can further have a substituent, and examples of the substituent include a halogen atom, an aryl group, an aryloxy group, an anobarynylsulfonyl group, an acylamino group, an alkoxy group, and a hydroxy group. etc.

The aryl group represented by R1 includes, for example, a phenyl group, and this aryl group can further have a substituent. Examples of the substituent include an alkyl group, a halogen atom, an alkoxy group, and an amide group.

The alkyl group represented by RZ in the general formula [T] is a linear or branched alkyl group having 1 to 30 carbon atoms, such as a methyl group, an ethyl group, an isopropyl group, a [-butyl group, an octyl group, Examples include a dodecyl group, a -[i]yl group, and a 1-lya=1-antyl group.

This argyl group can further have a substituent, and examples of the substituent include a halogen atom, an aryl group, an aryloxy group, an alkylsulfonyl group, an acylamino group, an alkoxy group, and a human[1xy group. Examples of alkyl groups having such substituents include:
Examples include γ-(2,4-di[-amylphenoxy)propyl group, β-(dodecylsulfonyl)ethyl group, phenoxymethyl group, me-1-xyethyl group, and benzyl group. The above alkyl group also includes a cycloalkyl group.

Examples of the aryl group represented by R1 include a phenyl group. This aryl group further has an @ substituent J
Examples of substituents include alkoxy groups,
Examples of aryl groups having a substituent include halogen atoms, alkyl groups, and amide groups. Examples include 4-di-t-amylphenoxy)butyrylamino)phenyl group, 0-chloro[1-phenyl group, P-1-lyl group, and mesityl (1-helimethylphenyl) group.

Examples of the heterocyclic group represented by R2 include furyl group,
Examples include a pyranyl group, a dienyl group, a pyridyl group, and a 21]-pyrrolyl group.

Among the alkyl group, aryl group, or heterocyclic group represented by R2, an alkyl group or an aryl group is particularly preferred. Furthermore, among the alkyl groups, dodecyl group, or γ-(
Among the 2,4-di-t-amylphenoxy)propyl group and the aryl group, a dodecyloxyphenyl group is particularly preferred.

The alkyl groups represented by R3 or R4 include straight chain or branched alkyl groups having 1 to 30 carbon atoms (these alkyl groups may have an unsaturated bond), such as methyl group, ethyl group, etc. group, isopropyl group, 1-butyl 1
Examples include a 11-ocdyl group, a dodecyl group, an eicosyl group, a 1- to 2-aryan diyl group, an allyl group, and a propargyl group.

This alkyl group can further have a substitution 1λ,
Examples of substituents include halogen atoms, aryl groups, aryloxy groups, alkylsulfonyl groups, acylamino groups, alkoxy groups, and hydroxy groups. Examples of alkyl groups having such substituents include ,
Examples include T-(2,4-di-1-amylphenoxy)p-1]pyl group, β-(dodecylsulfonyl)ethyl group, phenoxymethyl group, mehexyethyl group, and benzyl group. The above alkyl group also includes a cycloalkyl group.

The aryl group represented by R3 or Rc+'r is,
For example, phenyl group etc. can be mentioned. This aryl group can further have a substituent, and examples of the device 1@ group include an alkoxy group, a [1gen atom, an alkyl group, and an amide group. Examples include P-methoxyphenyl group, dodecyloxyphenyl group, P-(γ-(2,4-di[
-amylphTnoxy)butyrylamino)phenyl group, 0
-ri1-10 phenyl group, P-1~lyl group, mesidel (
trimederphenyl) group, etc.

Examples of the heterocyclic group represented by R3 or R include furyl group, pyranyl group, di1yl group, pyridyl group, 2H-
Examples include pyrrolyl group.

Among the alkyl groups, aryl groups, and heterocyclic groups represented by R3 or R1+, alkyl groups are particularly preferred. Among the alkyl groups, methyl, ethyl, benzyl and the like are particularly preferred.

Examples of the divalent bonding group represented by J include ethylene group, propylene group, 1-rimethylene group, 1-ethyl 1-
Examples thereof include a rimedylene group, a 1-heptyltrimedylene group, a dimethylmethylene group, a 1,1'-dimethylmethylene group, a phenyleneoxymonodimethylmethylene group, and the like.

Incidentally, -L-8ox -R2 is preferably at a position para to the chlorine atom at the 2-position of the anilide.

In the general formula [I], examples of groups that can be substituted on the benzene ring represented by B include halogen atoms, alkyl groups, alkoxy groups, aryloxy groups, acyloxy groups, acylamino groups, carbamoyl groups, and alkylsulfonamides. group, an arylsulfonamide group, a sulfamoyl group, or an imide group.

In the general formula [I], examples of the halogen atom represented by Z include a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, and the like.

In the general formula [I], examples of the group that can be substituted on the benzene ring represented by Z include an alkoxy group, an aryloxy group, an acyloxy group, and an alkoxy group is preferred, with a methoxy group being particularly preferred.

In the general formula [I], 7 is preferably a halogen atom, especially a chlorine atom.

In the general formula [I], examples of groups that can be substituted on the benzene ring represented by X and Y include nitro group, cyan group, carboxy group, sulfo group, alkoxycarbonyl group, carbamoyl group, acyl group, alkylsulfonyl group. group, arylsulfonyl group, alkoxysulfonyl group, sulfamoyl group, alkyl group, alkoxy group, halogen atom, and the like.

Typical specific examples of phenoxy groups substituted with X and Y are shown below.

Margin (a) 0C14H29 Hereinafter, typical examples of the yellow coupler represented by the above general formula [■] will be shown, but the present invention is not limited to these.

G (9) ct C.N. (→ ct (13ct (1pct J 0 → Ct OOH Below is a synthesis example of the above coupler.

Synthesis Example-1 (Synthesis of Exemplary Coupler (1)) α, -ri 1]
ru-α-Viva1]yl-2-ly[1-5-(β-dodecylsul-small-α-propanamide)ace1-anilide 6
, OgdoP-(I)-benzyloxyphenylsulfonyl) phenol 3.4q and acetone 1oon+i 1
．． 5 (j) Carbonic acid power 1 shim and distant current for 10 hours. After separating the insoluble matter and distilling off the acetone, add ethyl acetate and wash with dilute hydrochloric acid. After washing with water, ethyl acetate is distilled off. The product was purified by column chromatography for 11 Il to obtain 7.9 g of exemplified coupler (1).The obtained compound was confirmed by elemental analysis.

Synthesis Example-2 (Synthesis of Exemplary Coupler (16)) α-ri[''
7.2 g of α-pivaloyl-2-chloro-5-(N-benzyl-P-dodecylΔxybenzenesulfonamide)-acetanilide and 3.4 q of P-(1)-benzyloxyphenylsulfonyl)phenol were acetanilide. 1 hen 1
Fast flow for 8 hours with 1.50 potassium carbonate in 00 mβ. After filtering out the insoluble matter and distilling off the azene, add vinegar l! 11]
Add chill and wash with dilute hydrochloric acid.

After washing nine times with water, ethyl acetate was distilled off, and the mixture was separated and purified by column chromatography to obtain an 8,7σ exemplary coupler (16). Is the obtained compound confirmed by elemental analysis? １ノ lζ
.

The results of elemental analysis of the above-mentioned exemplary couplers are shown below.1-0 or less margin 1) The above-mentioned yellow couplers of the present invention can be used alone or in combination of two or more.

The yellow coupler of the present invention includes, for example, dibdelphthalate,
It has a boiling point of 175°C or higher, such as tricresyl phosphinyl 1-2, and is useful as a so-called protique 1-dispersion type coupler, which is used by dissolving it in a high-boiling organic solvent that is difficult to miscible with water. 112. Without using high boiling point organic solvents, substantially water-insoluble low boiling point organic solvents such as ethyl acetate and butyl acetate, or methanol, ethanol, methyl sesolv, methyl isobutyl kene, etc. It can also be used by dissolving only in a water-soluble low-boiling organic solvent. The yellow coupler of the present invention can also be used as a coupler for the so-called diffusion transfer method, in which a photosensitive element having a photosensitive layer is brought into contact with a processing sheet for the purpose of blocking light, etc. to form a transferred image on the image receiving layer of the image receiving element. It can also be used.

Moreover, the yellow coupler of the present invention is disclosed in Japanese Patent Publication No. 49-2658.
No. 5, U.S. Patent No. 3,486,890, Research Disclosure 1- (Reserct+[)
1sclousurc) No. 12044, same +
It can also be used in the dye image forming method described in No. 284 f1 and the like.

Moreover, both the yellow coupler of the present invention and the aromatic primary amine developing agent are contained in the photosensitive material 1! By imagewise exposure, processing with an alkali bath black and white 11 developing solution, or heat treatment, it is possible to perform color development and form a dye image with good gradation.

The color developing agent used in the present invention is an aromatic primary amine compound, and is a p-aminophenol or p-aminophenol compound.
Typical examples include phenylenediamine-based compounds, such as p-aminophenol, diethyl-〇-phenylenediamine hydrochloride, monomethyl-p-phenylenediamine salt M salt, dimethyl-〇-phenylenediamine salt M salt, 2-amino-5-diethylamino]helene hydrochloride,
2-amino-5-(N-ethyl-N-dodecylamino)
-1~luene, N-ethyl-N-β-methanesulfonamidoethyl-3-methyl-4-aminoaniline sulfur M salt,
N-ethyl-N-β-methanesulfonamidoethyl-4
-aminoaniline, 4-N-edyl-N-β-hydroxyethylaminoaniline, N-ethyl-N-β-meth1~
xy”nityl-3-methyl-4-aminoaniline, p-
Toluenesulfonate, N-ethyl-1'l [2-(
2-Methoxyethoxy)ethyl 1-3-methyl-4-aminoaniline, pt-luenesulfone 9m, N-ethyl-N-(2-[2-(2-methoxyethoxy)ethoxy1ethyl)-3-methyl -4-aminoaniline, p-
Examples include toluene sulfonate.

The present invention is also applicable to various color photographic materials, such as silver halide color photographic materials sensitive to electromagnetic energy such as ultraviolet light, visible light, infrared light, X-rays, γ-rays, and microwaves.

The above color developing agents may be used alone or in combination of two or more, and in the present invention, various components normally added to color developing solutions, such as alkaline agents such as sodium hydroxide, sodium carbonate, and potassium carbonate; Contains metal sulfites, alkali metal bisulfites, alkali metal thiocyanates, alkali metal halides, benzyl alcohol, thickening agents such as water softeners, and development control agents such as citradinic acid. can. The pH1ilJ of this color developer is usually above 71s,
The maximum temperature is generally between about 10 and about 13F.

The color developer used in the present invention can be used in combination with a black and white developer. The black-and-white developer is a so-called black-and-white first developer used in the processing of commonly known silver halide color photographic light-sensitive materials, or a black-and-white developer used in the processing of black-and-white photographic photosensitive materials, and is generally a black-and-white developer. Various well-known additives can be included. A typical additive is 1-phenyl-
Developing agents such as 3-pyrazolidones, methanol and hydroquinone, preservatives such as sulfites, accelerators consisting of alkalis such as boric acid hydroxide, thorium carbonate, potassium carbonate, potassium bromide. 2-methylbenzdeazole, inorganic or organic inhibitors such as methylbenzdeazole, water softeners such as polyphosphates,
Examples include surface overdevelopment inhibitors consisting of trace amounts of iodine and mercapto compounds.

In the present invention, after development with a color developer,
Any treatment can be performed, including bleaching, fixing, bleach-fixing, stabilization, washing with water, and stopping.

Bleach agents added to bleach or bleach-fix solutions include:
Preferred are metal complex salts of aminopolycarboxylic acids and/or metal complex salts of polycarboxylic acids, such as iron (IF) complex salts of ethylenediaminetetraacetic acid.

Further, the color development treatment may be performed two or more times, such as the first and second times.

Conventionally known methods can be used to incorporate the yellow coupler of the present invention into a silver halide photographic emulsion of a color photographic light-sensitive material. For example, as described above (when using the protect dispersion method, a high boiling point organic solvent with a boiling point of 175°C or higher such as tricresyl phosphate or dibutyl phthalate or a low boiling point organic solvent such as ethyl acetate or butyl propionate may be used alone or in a mixed solvent such as ethyl acetate or butyl propionate). After dissolving in 100 ml, it is mixed with an aqueous gelatin solution containing a surfactant, and then emulsified and dispersed in a high-speed rotating Millimeter or = 11" Idmil, and then directly added to a silver halide photographic emulsion.
The emulsified dispersion can be coated on a support and dried, or the emulsified dispersion can be dried, cut into pieces, the low boiling point solvent removed by washing with water, etc., the emulsion can be added to the emulsion, and the emulsion can be coated on a support and dried. Bye. In this case, it is generally preferable to add 10 to 300 g of the yellow coupler of the present invention per mole of silver halide, but it goes without saying that this may be varied depending on the purpose of application.

The silver halide photographic material to which the present invention is applied may be any material regardless of type or purpose. For example, it can be particularly advantageously used in multilayer negative color photographic materials, color print photographic materials, or JY color photographic materials for reversal color processing. and,
The silver halides used at this time include, for example, silver chloride, silver bromide, silver iodide, silver chlorobromide, silver iodobromide, silver chloroiodobromide, etc.
These silver halide emulsions are prepared by any known method. The silver halide emulsion may be, for example, a so-called conversion emulsion, a Lippmann emulsion, a covered silver twin emulsion, or one that has been optically or chemically fogged, depending on the type and use of the photographic material. -C is selected as appropriate. Also, the type of silver halide,
Silver halide content m and mixing ratio, average grain size,
Similarly, the size distribution and the like are appropriately selected depending on the type and use of the photographic material.

These silver halides include active gelatin: sulfur sensitizers, such as allylthiocarbamide, thiourea, cystine, etc.; selenium sensitizers: reduction sensitizers, such as stannous salts, polyamines, etc.; noble metal sensitizers, such as gold. Sensitizers specifically include potassium aurithiocyanate, potassium chloroole-1~,
Sensitizers such as 2-oresulbobenzothiazole methochloride or water-soluble salts such as ruthenium, rhodium, iridium, etc., specifically ammonium chlorovaladate, potassium chlorobratinate, sodium chlorobratinate, etc. These substances act as sensitizers or fog suppressants depending on the amount. and a selenium sensitizer, etc.) may be chemically sensitized.

Furthermore, this silver halide can be optically sensitized to a desired wavelength range, such as cellomethine dye, monomethine dye,
Optical sensitization can be carried out using optical sensitizers such as cyanine dyes such as dimethine dyes and trimethine dyes or merocyanine dyes alone or in combination (for example, supercolor sensitization).

This silver halide is dispersed in a suitable protective colloid to constitute a photosensitive layer, but as a protective colloid used in the composition of the photosensitive layer and other constituent layers such as an intermediate layer and a protective 4L filter layer, , alkaline-treated gelatin is common, and there are other synthetic resins such as acid-treated gelatin, derivative gelatin, colloidal albumin, cellulose derivatives, and polyvinyl compounds (e.g., polyvinyl alcohol), which can be used alone or in combination. However, acetyl cellulose having an acedel content of about 19 to 26%, water-soluble ethano-cyamine cell 1]-suacetate, etc. can also be used in combination.

The silver halide photographic material r1 according to the present invention may contain other color couplers together with the yellow coupler of the present invention in order to form a multicolor image. Other useful couplers include, for example, 5-pyrazolone magenta couplers, phenolic or nano-1-1-1 cyan couplers, and the like. In addition to these couplers, it is also possible to use azo-type colored couplers, ozazone-type compounds, development-diffusive dye-releasing couplers, etc. for auto-masking. Further, at this time, it is desirable to use a desired colorless coupler, which is colorless before color development, together with the above-mentioned masking coupler. Furthermore, various couplers such as so-called combining couplers, DIR couplers, F3AR (31each accelerat
or Releasing) couplers.

In the present invention, as a magenta coupler that can be used in combination with the yellow coupler of the present invention, C can be exemplified by compounds of the biran[1-one type, pyran-1-co-1-heliazole type, birazolinobenzimitazole type, and intazo[1-one type]. .

Examples of cyan couplers that can be used in combination with the yellow coupler of the present invention include phenolic compounds, active point -0-aryl-substituted naph]--al compounds, nano-1-al compounds, and the like.

The silver halide emulsion containing the yellow coupler of the present invention prepared as described above is layered on a support together with a subbing layer, an intermediate layer, a filter layer, a curl prevention layer, a protective layer, etc. as required. By doing so, a silver halide η true photosensitive material applicable to the present invention is prepared. Supports C that can be used at this time include paper, laminate 1-paper (for example, a laminate of polyethylene and paper), glass, cellulose, acetate-j-, cellulose 1-late, polyconistyl, polycarbonate. Examples include films or sheets of substrates such as polyamide, polymethinone, and polyolefin. The adhesion of the support to each constituent layer has been improved! Various surface treatments such as hydrophilic treatment can be performed for the purpose of, for example, /7 conversion treatment, ]f-1 treatment, subbing treatment, and res [- conversion treatment ■! Processing such as the following is performed.

The silver monogenide photographic photosensitive plate according to the present invention basically consists of at least a support and a photosensitive layer provided thereon, but as described above, it can be placed in various positions depending on the purpose. Generally, it is composed of several layers or more, with layers suitable for A layer containing silver halide of high sensitivity and a layer containing silver halide of relatively low sensitivity
It is constructed by layering a layer containing silver germide.
3J: Yes.

Further, the silver halide photographic light-sensitive material according to the present invention has a photosensitive layer and/or other constituent layers (for example, an intermediate layer, a subbing layer,
(filter layer, protective layer, image-receiving layer, etc.) may contain various photographic additives depending on the purpose. Examples of such photographic additives include stabilizers (mercury compounds, triazoles, azainzolones, quaternary benzothiazolium, zinc or cadmium salts, etc.), quaternary ammonium salts, polyamides, non-glycols, etc. Tfi sensitizers: substances such as glycerin, 4i-dihydroxyalkanes such as 1,5-pentadiol, esters of bisgrinyl acid, bis-1 hexydiethylene glycol, , amides of acrylic acids, emulsified dispersions of small aggregates, etc. Hardeners such as formaldehyde, mucochromic acid,
Halogen-substituted fatty acids such as mu]bu[1]muic acid, compounds containing acid anhydride groups, dicarboxylic acid chlorides, disulfonic acid silyl[]rides, vinylesters of methanesulfonic acid, aldehyde groups containing 2 to 3 carbon atoms by minute+1lIi
Dialdehydes used in bisulfite, thulium conductors, bisaziridine, tyrenimines, etc.: Extending agents such as 1 naponine, lauryl or oleyl monoether of polyethylene glycol, sulfated and alkylated polyethylene glycols. Salts, etc.: Coating aids, such as sulfosuccinates, etc. Two organic solvents, such as coupler solvents (high-boiling organic solvents and/or low-boiling organic solvents, specifically dibdeltstalate, ]] ~ Likuresil Small Sulfur x-l-1
7' Ketone methanol, earth tanol, -U tyrene l? Russorzo et al. 〉 ・The so-called 1) which releases a color development inhibitor and produces a substantially colorless compound during color development.
IR compound, its fine antistatic agent, foaming agent, ultraviolet absorber 1, fluorescent whitening agent, anti-slip +L agent, Pine 1~ agent, C I
Various anti-irradiation agents and anti-irradiation agents are used for 1) Dt and Dt, respectively.

The durability of the yellow image can be further improved by containing an ultraviolet absorber in the silver halide photographic material containing the yellow coupler of the present invention.

[Example 1] Next, the present invention will be explained in more detail with reference to Examples, but the embodiments of the present invention are not limited to these.

Example-1 As shown in Table 1, 3,0 x 10'-2 moles of each of the yellow couplers of the present invention (indicated by the numbers of the above-mentioned exemplary couplers) 63 and the following comparative couplers were added to 1 of the yellow couplers of 41. Jib delfta 1 no 1- corresponding to the weight of /2
and 7IOml of ethyl acetate, and heated to 50°C to completely dissolve]. This solution was mixed with 10ml of a 10% aqueous solution of alkanol-8 (alkylnaphthalene sulfone-1~, equipped with DuPont, the same applies hereinafter) and geladine 5.
% aqueous solution 2oom,,! The mixture was mixed and passed through a colloid mill several times to emulsify and create a dispersion. Add this dispersion to gelatin
The mixture was added to silver bromide emulsion 1OOOMJ7, coated on polyethylene laminate 1 on paper, and dried to prepare Sample 1 of silver bromide color photographic sensitivity. This sample was wedge exposed in the usual manner and processed according to the following steps and processing solution formulation.

Color 'Jd & 3 minutes 30 seconds bleach fixing 1 minute 30 seconds washing with water 2 minutes 0 seconds
Stabilization 1 minute 0 seconds "Color photographic developer" Benzyl alcohol 1.
Sodium bromide 1.40g Potassium bromide 0.50g Boric acid (Na2 B4077” 101-120) 3
9,40 QN-ethyl-11-[2-(methanesulfonamidoethyl)] -]3-methyl~4-aminoaniline sulfur 11Q salt 450 g Add water to make 111, botrium hydroxide 0 -1
Adjusted to 10.3.

[Bleach-fix solution] Ethylenediaminetetraacetate iron ammonium 61. oLJ ethylenediaminetetraacetate-2-ammonium 5. OQ Chio II
i! ammonium acid 124.5 (1
Metajuya 1iiiIII Sodium Sodium 13.3
Add 0M sodium sulfite 2.70 water to make 1f2, adjust the river to 6.5 and make 1.

[Stabilizing liquid 1 Wood vinegar M (trihydrate salt > 20 ml)
800 mJ2 of l' pure water was added, and FJF+ was prepared using acetic acid solution (3.5 to 4.0) using acetic acid solution (~rim trihydrate), and then finished to 1v.

Table 1 does not show the results of the dye image developed in the above article (1).

Table 1 (margin below) *Sensitivity is expressed as relative sensitivity with the sensitivity of sample No. 4 as 100.

The following margin comparison coupler (A) C4 CHs (Japanese Patent Application Laid-open No. 4.8-66835 (,
From the results in Table 1, the sensitivity of the present invention is It can be seen that a high and sufficient maximum concentration can be obtained.

Example-2 The following sample was created by performing the same operation as in Example-1,
Visual processing was performed.

In order to examine the light resistance of the 1q dye image, it was irradiated with a xenon fade meter for 100 hours, and the density after exposure at an initial density of 1.0 is shown in Table 2 as the dye residual rate.

From the results shown in Table 2 for Coupler, it can be seen that the dye images obtained in the present invention have excellent light resistance.

Margin Example-3 The amount of dibutylphta 1 note was changed as shown in Table 3 using the example coupler (1) and comparative coupler (D).
Except for the above, a sample of a silver hagenide color photographic light-sensitive material was prepared in the same manner as in Example 1, and the same treatment was carried out.

The results are shown in Table 3, and it can be seen that the yellow coupler of the present invention has excellent solubility and dispersion stability, and has stable color development without being significantly affected by changes in the amount of high boiling point solvent on photographic properties.

Table 3 Example-4 The amount of dibutyl phthalate was varied as shown in Table 4 using the illustrative coupler (5) and the comparative coupler (C). The same processing was carried out using the same silver halide color photographic light-sensitive material as in Example 1, except that the darkness of the benzyl alcohol added to the liquid was changed to s, om, ((usually used).

As shown in Table 4, the results show that the yellow coupler of the present invention has the same solubility and dispersion stability as in Example 3, and exhibits stable color development without any significant effect on photographic properties due to changes in the amount of high-boiling solvent. I understand that.

Below margin Table 4

Claims (1)

[Scope of Claims] A silver halide photographic material characterized by containing a coupler represented by the following general formula [I]. General formula [I] ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (In the formula, R_1 represents an alkyl group, cycloalkyl group, or aryl group, and L is ▲There are mathematical formulas, chemical formulas, tables, etc.▼ or ▲Mathematical formulas, chemical formulas) There are tables, etc. ▼-CO-
J-[R_3 represents an alkyl group, aryl group or heterocyclic group, R_4 represents a hydrogen atom or a group having the same meaning as R_3 above, and J represents a divalent bonding group. ], R
_2 represents an alkyl group, an aryl group, or a heterocyclic group, Z represents a hydrogen atom, a halogen atom, or a group that can be substituted on a benzene ring, X and Y represent a hydrogen atom or a group that can be substituted on a benzene ring, and B represents a group that can be substituted on the benzene ring, and n represents 0 or 1. )