JPS62297844A - Silver halide photographic sensitive material having novel cyan dye forming coupler - Google Patents

Abstract

PURPOSE:To obtain a silver halide photographic sensitive material contg. a cyan dye forming coupler which has good color formability and has the excellent fastness of the formed cyan dye to light and heat by incorporating the specific cyan dye forming coupler into at least one silver halide emulsion layer. CONSTITUTION:The cyan dye forming coupler expressed by the formula is incorporated into at least one silver halide emulsion layer formed on a base. In the formula, R<1> is an alkylene group, R<2> is an aryl group, R<3> is alkyl group of <=4 C, X is hydrogen atom or group which can be eliminated by coupling with the oxidant of a developing agent. The alkylene expressed by R<1> is preferably the group expressed by -CH(-R)- (-R is the alkyl group bonded to the side chain). The group which is expressed by X and can be eliminated is preferably a halogen atom, aryloxy group and more particularly preferably chlorine atom.

Description

DETAILED DESCRIPTION OF THE INVENTION (Field of Industrial Application) The present invention relates to a silver halide color photographic light-sensitive material containing a cyan coupler having good fastness to light and heat and good color development.

(Background of the Invention) In conventional silver halide photographic materials, exposed silver halide grains are reduced with an aromatic primary amine color developing agent, and the oxidation products of the color developing agent and the yellow , magenta and cyan dye forming couplers in a silver halide emulsion layer, a color dye image can be obtained.

The couplers commonly used to form the cyan dyes are phenols or naphthols.

However, several problems remain in the storage stability of color images obtained from conventionally used phenols and naphthols. For example, U.S. Patent 2,367.531
and:! The color images obtained with the 2-acylaminophenolic cyan couplers described in U.S. Pat. No. 423,730 generally have poor heat fastness;
29, and 2 described in specification 2.772.162.
, 5-diacylamine phenolic cyan colorants generally have poor light fastness, and 1-hydroxy-2-natutamido cyan colorants are generally insufficient in both light and heat fastness.

On the other hand, U.S. Patent No. 4.122.396 and JP-A-57
The 2,5-diacylaminophenol cyan coupler described in specifications such as No. 155538 and JP-A No. 57-157246 has better robustness than the general cyan coupler mentioned above, and also has higher boiling point organic Although it has features such as good solubility in solvents, it is still not at a fully satisfactory level and has the disadvantages of not being able to withstand long-term storage and being prone to crystallization when added to photographic emulsions.

Although various cyan dye-forming couplers are known in addition to the couplers mentioned above, a satisfactory cyan dye-forming coupler that has good color forming properties and poor fastness to light and heat has not yet been obtained. The reality is that this is not the case.

(Object of the Invention) Therefore, the object of the present invention is to provide a silver halide photographic photosensitive material containing a cyan dye-forming coupler, which has good color forming properties and has excellent fastness to light and heat of the cyan dye formed. The goal is to provide materials.

(Structure of the Invention) An object of the present invention is to provide a silver halide photographic material having at least one silver halide emulsion layer on a support, in which at least one of the silver halide emulsion layers has the following general formula [TJ The following margin is achieved by a silver halide photographic light-sensitive material containing a cyan dye-forming coupler represented by the general formula [I] (wherein R1 represents an alkylene group, R2 represents an aryl group, and R3 represents a carbon atom). (Represents an alkyl group of the number 4 or less, and X represents a hydrogen atom or a group that can be eliminated by coupling with an oxidized product of a developing crude drug.) (Specific constitution of the invention) In the general formula [I], The alkylene group represented by R1 may be linear or branched, and preferably has 1 to 20 carbon atoms. The alkylene group represented by R1 is particularly of the formula CH- (wherein R represents an alkyl group).

) is preferred. Examples of the alkyl group represented by R include ethyl group, propyl group,
Examples include butyl group, decyl group, dodecyl group, and the like.

Wear.

In the general formula [I], the group that can be eliminated by coupling with the oxidized product of the phenomenon agent represented by X is:
A halogen atom and an aryloxy group (for example, a p-methoxyphenoxy group, a p-octylphenoxy group, etc.) are preferred, a halogen atom is particularly preferred, and a chlorine atom is especially preferred.

Specific examples of the cyan dye-forming coupler represented by the general formula [I] according to the present invention (hereinafter referred to as the cyan coupler according to the present invention) are shown below, but the present invention is not limited thereto.

The following are blank exemplified compounds: CaH2 CH3 ctz&s In the general formula [I], examples of the aryl group represented by R2 include a phenyl group and a naphthyl group, with a phenyl group being preferred.

These aryl groups include those having substituents, and there may be two or more substituents. Examples of substituents include halogen atoms, alkyl groups, aryl groups, and I)
Examples include dissociative groups having a Ka of 6 to 12 and substituents containing these dissociative groups. Specifically, in addition to the above-mentioned halogen atoms and alkyl groups, examples include hydroxyl groups, sulfonyl groups, sulfonamide groups, etc. can be mentioned.

Here, examples of the halogen atom include a chlorine atom, a bromine atom, etc., and chlorine atoms are particularly preferred.

Examples of alkyl groups include methyl group, ethyl group, i
-propyl group, t-butyl group, [-pentyl group, pentadecyl group, etc., and these alkyl groups may further have a substituent.

Examples of the sulfonyl group include alkylsulfonyl groups such as a methylsulfonyl group, and arylsulfonyl groups such as a phenylsulfonyl group. Examples of sulfonamide groups include alkylsulfonamide groups such as butylsulfonylamino group and dodecylsulfonylamino group; 7-arylsulfonamide groups such as p-toluenesulfonamide group and dodecylbenzenesulfonamide group; dimethyl Examples include alkylaminosulfonamide groups such as aminosulfonamide groups.

In the general formula [I], the alkyl group having 4 or less carbon atoms represented by R3 includes, for example, a methyl group, an ethyl group, an n-propyl group, an n-butyl group, and the like.

In the general formula [I], the group that can be eliminated by coupling with the oxidized product of the developing agent represented by X is:
For example, a halogen atom (specifically, each atom such as chlorine, bromine, or fluorine), an aryloxy group, a carbamoyloxy group, a carbamoylmethoxy group, an acyloxy group, or a sulfone in which an oxygen atom or a nitrogen atom is directly bonded to the coupling position. Examples include amide group, succinimide group, etc. Synthesis Example 1 Synthesis of Exemplary Compound 4
-2,4-di-t-amylphenoxy)-isovaleramide]phenol 30o was added to g. 40
was dissolved in 15i12 of water and added to 1,401 g of methanol, and the mixture was added with stirring and stirred at subtemperature for 40 minutes. After the reaction was completed, the reaction solution was poured into ice water 6009 containing concentrated salt M 3 5 1Q, and a solid was precipitated.

The obtained solid was collected by filtration, washed with water, and dried.

Recrystallization from acetonitrile yielded 22.3 g'R of Exemplified Compound 4 as a white powder.

Melting point: 178.0-1810°C Synthesis Example 2 Synthesis of Exemplified Compound 10
- (4-acetoxy3-t-butylphenoxy) myristic acid amide] 340 g of phenol was added to 8 g of caustic soda.
．． 40() was dissolved in 15i of water and added with 1401g of methanol, and stirred for 20 minutes at the lowest temperature.After the reaction was completed, the reaction solution was added to 6009g of ice water containing mfMM35d.
Upon entry, a viscous solid precipitated out. Next, ethyl acetate 5001I2 was added for extraction, the aqueous layer was removed, and the mixture was washed twice with 600ml of saturated saline. After dehydrating the ethyl acetate layer by adding anhydrous magnesium sulfate, the magnesium sulfate was removed by filtration, and the ethyl acetate was condensed 3i3. When the residual candy-like substance was recrystallized from 601 g of acetonitrile, 20
．． 6 g of Exemplified Compound 10 was obtained.

Melting point: 119-121°C Synthesis Example 3 Synthesis of Exemplified Compound 15 Exemplified Compound 15 was obtained in the same manner as in Synthesis Example 2 except that ethanol was used instead of methanol.

Melting point: 130-133° C. The methods and techniques used in conventional cyan dye-forming couplers can be similarly applied to the cyan coupler according to the present invention. Typically, the cyan coupler according to the present invention is blended into a silver halide emulsion, and the silver halide photographic light-sensitive material of the present invention is formed by coating this emulsion onto a support.

The silver halide photographic light-sensitive material of the present invention can be a monochromatic or multicolor silver halide photographic light-sensitive material. In multicolor silver halide photographic materials, the cyan coupler according to the present invention is usually contained in the red-sensitive silver halide emulsion layer, but it may also be contained in the non-sensitized emulsion layer. Multicolor silver halide photographic materials have dye image-forming units that are sensitive to each of the three primary color regions of the spectrum.

Each constituent layer can consist of a single or multiple emulsion layer sensitive to a certain region of the spectrum. The constituent layers of the silver halide photographic material, including the layers of image-forming constituent units, can be arranged in various orders as known in the art. A typical multicolor silver halide photographic light-sensitive material consists of a cyan dye image-forming unit consisting of at least one red-sensitive silver halide emulsion layer containing at least one cyan dye-forming coupler (at least one cyan dye-forming coupler). one is a cyan coupler according to the invention), a magenta dye image-forming composition comprising at least one green-sensitive silver halide emulsion layer containing at least one magenta dye-forming coupler;
It consists of a yellow dye image-forming structural unit supported on a support, comprising at least one blue-sensitive silver halide emulsion layer containing at least one yellow dye-forming coupler. Silver halide photographic materials have additional,
For example, it can have a filter layer, an intermediate layer, a 1L undercoat layer, etc.

In order to incorporate the cyan coupler according to the present invention into an emulsion, a conventionally known method may be followed. For example, the present invention can be applied to a high boiling point solvent such as tricresyl phosphate or dibutyl phthalate having a boiling point of 175°C or higher, or a low boiling point solvent such as butyl acetate or butyl propionate, each alone or as a mixture thereof as necessary. After dissolving the cyan coupler according to the invention alone or in combination, it is mixed with an aqueous gelatin solution containing a surfactant, and then added to the emulsified halogenated compound using a high-speed rotary mixer or a colloid mill. A silver halide emulsion for use can be prepared.

When the shear coupler according to the present invention is added to the silver halide emulsion used in the present invention, it is usually 0.07 to 0.7 mol per 1 mol of silver halide, preferably 0.01r.
It is added in an amount of ~0.4 mol.

Silver halide compositions preferably used in the present invention include silver chloride, silver chlorobromide, and silver chloroiodobromide. Further, it may be a combination mixture such as a mixture of silver chloride and silver bromide. That is, when the silver halide emulsion according to the present invention is used in color photographic paper, particularly fast developability is required, so it is preferable that the halogen composition of the silver halide contains chlorine atoms, and at least 1% of the chlorine atoms. Particularly preferred are silver chloride, silver chlorobromide, or silver chloroiodobromide containing silver chloride.

The silver halide used in the present invention may be a monodisperse emulsion in which the average grain size is distributed over a wide range, but a substantially monodisperse emulsion is preferred.

In the present invention, the above-mentioned substantially monodisperse silver halide grains are those in which most of the silver halide grains appear to have the same shape and uniform grain size when the emulsion is observed using an electron microscope, and are as follows: It has a particle size distribution as defined by the formula:

That is, when the standard deviation S of the particle size distribution is divided by the average particle size r, it is 0.15 or less.

In addition, the crystals of these silver halide grains may be normal crystals, twin crystals, or other crystals, and have (1,0,0) planes and (1,1
, 1) Any surface ratio can be used.

Further, the crystal structure of these silver halide grains may be uniform from the inside to the outside, or may have a layered structure (core-shell type) in which the inside and outside are different. Further, these silver halides may be of a type that forms a latent image mainly on the surface or of a type that forms a latent image inside the grain. In addition, tabular silver halide grains (Japanese Patent Application 1983-
170070) can also be used.

The substantially monodisperse silver halide grains preferably used in the present invention may be obtained by any conventional preparation method such as an acid method, a neutral method, or an ammonia method.

Alternatively, for example, seed particles may be produced using an acidic method, and then grown using an ammonia method, which has a high growth rate, to grow to a predetermined size. When growing silver halide grains, the amount of DHll) A (1, etc.) in the reaction vessel is controlled, and an amount commensurate with the growth rate of silver halide grains as described in JP-A No. 54-48521 is controlled. It is preferable to simultaneously implant and mix silver ions and halide ions.

Preferably, the silver halide grains according to the present invention are prepared as described above. A composition containing the silver halide grains is referred to herein as a silver halide emulsion.

These silver halide emulsions are composed of active gelatin: sulfur sensitizers such as allylthiocarbamide, thiourea, cystine, etc.: selenium sensitizers, dual reduction sensitizers such as stannous salts, thiourea dioxide, Polyamines, etc.: Noble metal sensitizers, such as gold sensitizers, specifically potassium aurithiocyanate, potassium chloroaurate, 2-aurothio-3-
Sensitizers such as methylbenzothiazolium chloride or water-soluble salts such as ruthenium, palladium, platinum, rhodium, iridium, etc., specifically ammonium chlorovaladate, potassium chloroaurate and sodium chlorovaladate (these Depending on the size of l, these substances act as sensitizers or fog suppressants. It may also be chemically sensitized (for example, in combination with a sensitizer).

The silver halide emulsion according to the present invention is chemically ripened by adding a sulfur-containing compound, and before, during, or after this chemical ripening, a nitrogen-containing emulsion having at least one hydroxytetrazaindene and mercapto group is produced. It may also contain at least one type of terocyclic compound.

The silver halide used in the present invention is prepared by adding a sensitizing dye of 5 x 104 to 3 x 10-3 mol per 1 mol of silver halide to impart photosensitivity to the desired wavelength range. It may be optically sensitized.

Various sensitizing dyes can be used, including cyanine dyes, merocyanine dyes, monocyanine dyes, composite merocyanine dyes, holopolar cyanine dyes, hemicyanine dyes, steryl dyes, and hemioxanol dyes. Can be done.

Particularly useful dyes include cyanine dyes, merocyanine dyes,
and a complex merocyanine pigment. Any of the nuclei commonly used for cyanine dyes can be used as the basic heterocyclic nucleus for these dyes. That is, pyrroline nucleus, oxazoline nucleus, thiazoline nucleus, virol nucleus, oxazole nucleus, thiazole nucleus, selenazole nucleus, imidazole nucleus, tetrazole nucleus, pyridine nucleus, and a nucleus in which an alicyclic hydrocarbon ring is fused to these nuclei: and these. A nucleus in which an aromatic hydrocarbon ring is fused to the nucleus, that is, an indolenine nucleus,
Benzindolenine nucleus, indole nucleus, benzoxazole nucleus, naphthoxazole nucleus, benzothiazole nucleus,
These include naphthothiazole nucleus, benzoselenazole nucleus, benzimidazole nucleus, and quinoline nucleus. These nuclei may be substituted on carbon atoms.

Merocyanine dyes or composite merocyanine dyes include a pyrazolin-5-one nucleus, a thiohydantoin nucleus, and a 2-thioxazolidine-2 nucleus having a ketomethylene structure.
, 4-dione, thiazolidine-2,4-dione, rhodanine, and thiobarbic acid nuclei can be used.

Useful sensitizing dyes used in blue-sensitive silver halide emulsion layers include, for example, West German Patent No. 929.080, US Pat. No. 2,231,658, US Pat.
, 503, No. 776, No. 2,519,001, No. 2
, No. 912,329, No. 3, No. 656.959, No. 3
．． No. 672.897, No. 3,694,217, No. 1
Examples include those described in Japanese Patent No. 1,025,349, British Patent No. 4,046,572, British Patent No. 1,242.588, Japanese Patent Publication No. 44-14030, Japanese Patent Publication No. 52-24844, and the like. Further, useful sensitizing dyes used in green-sensitive silver halide emulsions include, for example, U.S. Pat. No. 1.939.
No. 201, No. 2,072.908, No. 2.739.
No. 149, No. 2,945,763, British Patent No. 505
．． Representative examples thereof include cyanine dyes, merocyanine dyes, and composite cyanine dyes as described in No. 979 and the like.

Furthermore, useful sensitizing dyes used in red-sensitive silver halide emulsions include, for example, U.S. Pat.
Typical examples thereof include cyanine dyes, merocyanine dyes, and composite cyanine dyes as described in Japanese Patent No. 2.454, No. 629, No. 2,776.280, and the like. Furthermore, U.S. Patent Nos. 2,213,995, 2,493,748, 2,519,001,
Cyanine dyes, merocyanine dyes or composite cyanine dyes such as those described in German Patent No. 929.080 can be advantageously used in green-sensitive silver halide emulsions or red-sensitive halogen emulsions.

These sensitizing dyes may be used alone or in combination. Combinations of sensitizing dyes are often used, especially for the purpose of supersensitization. Typical examples are Special Publications No. 43-4932, No. 43-4933, and No. 43-4933.
No. 43-4936, No. 44-32753, No. 45-2
No. 5831, No. 45-26474, No. 46-1162
No. 7, No. 46-18107, No. 47-8741,
No. 47-11114, No. 47-25379, No. 47
-37443, 48-28293, 48-38
No. 406, No. 48-38407, No. 48-38408
No. 48-41203, No. 48-41204, No. 49-6207, No. 50-40662, No. 53-1
2.375, 54-34535, 55-156
No. 9, JP-A No. 50-33220, JP-A No. 50-33828
No. 50-38526, No. 51-107127,
51-115820, 51-+35528, 51-151527, 52-23931,
No. 52-51932, No. 52-10491.6, No. 52-104917, No. 52-109925, No. 5
No. 2-110.618, No. 54-80118, No. 56
-257?8, 571483, 58-1075
No. 3, No. 58-91445, No. 58-153926, No. 59-114533, No. 59-116645,
fiil 59-116647M, US '5 Q8 rF
2.688.545, 2.977.229, 2.688.545, 2.977.229,
No. 3,397,060, No. 3,506,443, No. 3,578,447, No. 3.672.89111,
It is described in 3.679.428, 3.769.301, 3,814,609, and 3,837°862.

Dyes that do not themselves have a spectral sensitizing effect, or substances that do not substantially absorb visible light and exhibit supersensitization, which are used with sensitizing dyes, include: (1) aromatic acid formaldehyde; Condensates (e.g., U.S. Pat.
, 437,510), cadmium salts, azaindene compounds, aminostilbene compounds substituted with nitrogen-containing heterocyclic groups (e.g., U.S. Pat. No. 2,933,39
No. 0, No. 3,635,721), etc. U.S. Patent Nos. 3,615,613 and 3,615,64
No. 1, No. 3,617.295, No. 3,635°721
The combinations described in this issue are particularly useful.

Antifoggants and stabilizers can be added to the silver halide photographic material of the present invention for the purpose of preventing fog during storage over time and during engraving.

As an antifoggant and stabilizer, US time i 2,713
．． 541. %, No. 2,743,180, No. 2.743
．． Pentazaindenes described in US Pat. No. 181, US Pat. No. 2,716,062, US Pat. No. 2,444,607, US Pat.
No. 2,835,581, No. 2.852.375, Research Disclosure (Research [)
1sclosure) Tetrazaindenes described in No. 14851, triazaindenes described in U.S. Pat.
Azaindenes such as polymerized azaindenes described in US Pat. No. 1142; thiazolium salts described in US Pat. 3,148,067
Byrylium salts described in the No. 1987-406
Quaternary onium salts such as phosphonium salts described in No. 65: U.S. Patent Nos. 2,403,927 and 3,266.8
No. 97, No. 3.708.303, Japanese Unexamined Patent Publication No. 1983-135
Mercaptotetrazoles, mercaptotriazoles, and mercaptodiazoles described in No. 835 and No. 59-71047, mercaptothiazoles described in U.S. Pat. No. 2,824,001, and U.S. Pat.
, mercaptobenzthiazoles and mercaptobenzimidazoles described in U.S. Patent No. 987, US Pat.
Mercapto-substituted heterocyclic compounds such as mercaptooxadiazoles described in U.S. Pat. No. 3.491 and mercaptothiadiazoles described in U.S. Pat. No. 3.364.028: U.S. Pat. 43-1
Catechols described in No. 0256, Special Publication No. 56-4
Resorcinols described in No. 4413 and Japanese Patent Publication No. 43
- Polyhydroxybenzenes such as gallic acid esters described in No. 4133; Tetrazoles described in West German Patent No. 1,189°380; US vI Patent No. 3, 157.5
Triazoles described in No. 09, U.S. Pat. No. 2.70
Benztriazoles described in U.S. Pat. No. 4.721, urazoles described in U.S. Pat. No. 3,287.135,
Azoles such as pyrazoles described in U.S. Pat. No. 3.106.467, indazoles described in U.S. Pat. No. 2.271.229, and polymerized benztriazoles described in JP-A-59-90844. and pyrimidines described in U.S. Pat. No. 3,161,515,
Heterocyclic compounds such as 3-pyrazolidones described in U.S. Pat. No. 2,751,297 and polymerized pyrrolidones or polyvinyl pyrrolidones described in U.S. Pat. -130929,
Various inhibitor precursors described in US Pat. No. 59-137945, No. 140445, British Patent No. 1.356,142, US Pat. Sulfinic acid and sulfonic acid derivatives described in US Pat. No. 047.393: US Patent 2.
566, No. 266, No. 2.839,405, No. 2,
There are inorganic salts described in No. 488.709 and No. 2,728,663.

It is advantageous to use gelatin as the binder (or protective colloid) for the silver halide emulsion according to the invention, but gelatin derivatives, graft polymers of gelatin and other polymers, other proteins, sugar derivatives, and cellulose may also be used. Existing aqueous colloids such as synthetic hydrophilic polymeric materials such as derivatives, monopolymers, or copolymers can also be used.

When gelatin is used as a binder (or protective colloid) for the silver halide emulsion according to the present invention, the jelly strength of gelatin is not limited, but the jelly strength is 250 g.
It is preferable that it is above (@ measured by the baggy method).

The silver halide photosensitive material ♀ photographic emulsion layer and other hydrophilic colloid layers according to the present invention are produced by using one or more hardeners that crosslink binder (or protective colloid) molecules and increase the printing strength. ii! It can be membraned. The hardening agent can be added to the processing solution to harden the photosensitive material to such an extent that it is not necessary to add the hardening agent, but it is also possible to add the hardening agent to the processing solution.

A plasticizer may be added to the silver halide emulsion layer and/or the hydrophilic colloid layer of the halogen 1 photosensitive material according to the present invention for the purpose of increasing flexibility.

The photographic emulsion layer of the silver halide light-sensitive material of the present invention and the hydrophilic colloid layer may contain a dispersion (latex) of a water-insoluble or sparingly soluble synthetic polymer for the purpose of improving one-method stability. can.

The emulsion layer of the light-sensitive material of the present invention undergoes a coupling reaction with an oxidized form of an aromatic primary amine developer (for example, p-phenylenediamine derivatives, aminophenol derivatives, etc.) during color development processing to form a dye. A dye-forming coupler is used.

The dye-forming couplers are typically selected for each emulsion layer such that a dye is formed that absorbs light in the light-sensitive spectrum of the emulsion layer, with a yellow dye-forming coupler for the blue-sensitive emulsion layer and a dye for the green-sensitive emulsion layer. A magenta dye-forming coupler is used in the sensitive emulsion layer and a cyan dye-forming coupler is used in the red-sensitive emulsion layer. However, depending on the purpose, silver halide color photographic materials may be produced using different combinations from the above.

It is desirable that these dye-forming couplers have a group called a ballast group in the molecule, which is carbon'118 or more and makes the coupler non-diffusive.
Either the 4-equivalence type, in which 4 molecules of silver ions need to be reduced to form a molecular dye, or the 2-equivalence type, in which only 2 molecules of silver ions need to be reduced, may be used.

Dye-forming couplers can be combined with oxidized developing agents to produce development accelerators, bleaching accelerators, developing agents, silver halide solvents, toning agents, hardeners, fogging agents, antifogging agents,
Compounds that release photographically useful fragments such as chemical sensitizers, spectral sensitizers, and desensitizers can be included. Colored couplers that have a color correction effect on these dye-forming couplers, or DiR couplers that release development inhibitors during development and improve image sharpness and image graininess, impair the effects of the present invention. They may be used together within the range. In this case, it is preferable that the dye formed from the DIR coupler is of the same type as the dye formed from the dye-forming coupler used in the same emulsion layer, but if the color turbidity is not noticeable, a different type of dye may be used. It may also be one that forms a pigment. Instead of the DIR coupler, a DIR compound that is used with or in combination with the coupler to undergo a coupling reaction with the oxidized form of the developing agent to produce a colorless compound and at the same time release a development inhibitor may be used within a range that does not impair the effects of the present invention. It's okay.

DIR couplers and DIR compounds that may be used in combination include:
In some cases, the inhibitor is directly bonded to the coupling position, and in others, the suppressor is bonded to the coupling position via a divalent group, and an intramolecular nucleophilic reaction within the group separated by the coupling reaction or an intramolecular Included are those bound in such a way that the inhibitor is released by an electron transfer reaction or the like (referred to as timing DIR couplers and timing DIR compounds). Also, depending on the purpose, inhibitors that can be dispersed after release and those that are not so dispersible can be used alone or in combination. A colorless coupler that undergoes a coupling reaction with an oxidized form of an aromatic primary amine developer but does not form a dye may also be used in combination with a dye-forming coupler.

As the yellow dye-forming coupler (yellow coupler) used in the present invention, various acylacetanilide couplers can be preferably used. Among these, benzoylacetanilide and pivaloylacetanilide compounds are advantageous. Specific examples of yellow couplers that can be used include British Patent No. 1,077.874 and Japanese Patent Publication No. 1977.
-40757, W 47-1031, 47-2
No. 6133, No. 48-94432, No. 50-8765
No. 0, No. 51-3631, No. 52-115219,
No. 54-99433, No. 54-133329, No. 5
G-30127, U.S. Patent No. 2,875,057, U.S. Patent No. 3.253.924, U.S. Patent No. 3.265.506,
3.408.194, 3,551,155, 3,551.156, 3.664.841, 3.725.072, 3.730,722, 3, 891,4.15, 3.900,483, 3.929.484, 3.933°500,
3.973.968, 3.990.896, 4,012,259, 4,022゜620@,
4,029,508, 4.057,432, 4, 106.942, 4.133.958, 4,269,936, 4.286.053, 4, No. 304,845, No. 4,314,023, No. 4
, No. 336, 327, No. 4.356.258, No. 4.
386'.

No. 155, No. 4.401.752, etc.

As the magenta dye-forming coupler (magenta coupler), various 5-razolone couplers, lazolopenzimidazole couplers, pyrazoloazole couplers such as pyrazolotriazole, and open-chain acylacetonitrile couplers are preferably used. Can be done. Specific examples of magenta couplers that can be advantageously used are disclosed in Japanese Patent Application No. 58-1.
No. 64882, No. 58-167326, No. 58-20
No. 6321, No. 5g-214863, No. 58-217
No. 339, No. 59-24653, Special Publication No. 40-603
No. 1, No. 40-6035, No. 45-40757,
47-27411, 49-37854, JP-A-50-13041, 51-26541, 51-
No. 37646, No. 51-105820, No. 52-42
No. 121, No. 53-123129, No. 53-12
No. 5835, No. 53-129035, No. 54-485
No. 40, No. 56-29236, No. 56-75648, No. 57-17950, No. 57-35858, No. 5
No. 7-146251, No. 59-99437, British Patent No. 1,252°418, U.S. Patent No. 2,600.78
No. 8, No. 3.005.712, No. 3.062.653
No. 3,127,269, No. 3,214゜437, No. 3.253.924, No. 3,311,476,
3.419,391, 3,519,429,
No. 3,558,319, No. 3.582.322,
3.615.506, 3.658.5471,
3.705.896, 3.725.067, 3.758゜309, 3,823,156, 3
．． No. 834□908, No. 3, No. 891.445, No. 3
．． No. 907.571, No. 3.926.631, No. 3,
No. 928,044, No. 3,935,015, No. 3.9
60.571, 4.076, 533, 4.13
3.686, 4,237゜217, 4,241
, No. 168, No. 4.264.723, No. 4.301,
No. 235, No. 4,310,623, etc.

As a cyan dye-forming coupler (cyan coupler),
In addition to the cyan coupler according to the present invention, various naphthol couplers and phenol couplers can be used in combination. Specific examples of cyan couplers that can be advantageously used include British Patent Nos. 1,038,331 and 1,543,040;
JP 48-36894, JP 9-11st 2, JP 48-59838, JP 50-137137, JP 51-. No. 1-46828, No. 53-405226, No. 54-115230, No. 56-29235,
No. 56-104333, No. 56-126833, No. 57-133650, No. 57-155538,
No. 57-204545, No. 58-118643, No. 59-31953, No. 59-31954, No. 59-
No. 59656, No. 59-124341, No. 59-16
6956N, U.S. Pat. No. 2.369.929, 2.
No. 423.730, No. 2,434,272, No. 2.4
No. 74.293, No. 2.698.794, No. 2,77
No. 2,162, No. 2,801,171, No. 2,895
No. 826, No. 3.253.924, No. 3,311,
No. 476, No. 3, No. 458.315, No. 3.476,
No. 563, No. 3.591, 383, No. 3.737.
No. 316, No. 3.758.308, No. 3.7-6-7
．． No. 41', No. 3.772.002, No. 3.790.
No. 384, No. 3.880゜661, No. 3.926.6
No. 34, No. 4.004.929, No. 4, 009.03
No. 5, No. 4.012.258, No. 4.052.2
No. 12, No. 4,1211.396, No. 4.134.7
No. 66, No. 4,138,258, No. 4,146,39
No. 6, No. 4.149.886, No. 4,178°183
No. 4.205.990, No. 4.254,212, No. 4.264,722, No. 4.288.532, No. 4.296.199, No. 4.296.200, 4.299.914, 4.333.999,
These are described in No. 4,334,011, No. 4,386.155, No. 4,401°752@, No. 4,427,767, etc.

As a colored coupler, for example, British Patent No. 937.
No. 621, No. 1.035.959, No. 1,255
, No. 111, JP-A-48-22028, JP-A No. 52-42
No. 121, Special Publication No. 38-22335, No. 44-201
No. 6, No. 44-15754, U.S. Patent No. 2.449.
No. 96-6, No. 2,521,908, No. 2,543
, No. 691, No. 2,801,111, No. 2.983
．． No. 608, No. 3,005.712, No. 3.034
．． No. 892, No. 3.061.432, No. 3,419°391, No. 3.476, No. 560, No. 3.476, 5
No. 63, No. 3.481,741, No. 3,519,4
No. 29, No. 3.583.971, No. 3,622,3
No. 28, No. 3,684,514, No. 4.004.92
No. 9, No. 4.070.191, No. 4,138,258
No. A, No. 138゜264, No. 4.163.670
No. 4.292. aoo issue, 4.369, 24a
You can use those listed in the No.

As a DIR coupler, for example, British Patent No. 953,1
No. 154, U.S. Patent No. 3.227.554, U.S. Patent No. 3,6
15゜506, same, 3,617,291, same 3.7
0i, No. 783, No. 3, No. 933.500, No. 4.
No. 095.984, No. 4.149.886, No. 4
．． No. 286.054, same tl, No. 359,521, special! Compounds described in 51-90932, 56-116029, 57-151944, etc., and U.S. Pat. , 58-162949
No. 58-205150, No. 59-195643, No. 59-206834, No. 59-206836,
Timing DIR couplers described in Japanese Patent No. 59-210440, Japanese Patent No. 60-7429, etc. can be preferably used.

DIR compounds include, for example, U.S. Pat. No. 3,632;
No. 345, No. 3.928.041, No. 3.938
．． No. 996, No. 3, No. 958.993, No. 3,961
, No. 959, 4.046.574@, C052,
No. 213, No. 4,171,223, No. 4.186.0
No. 12, JP-A No. 52-65433, JP-A No. 52-1303
Compounds described in No. 27, No. 57-128335, etc. can be preferably used.

As colorless couplers, U.S. Patent No. 2,998,314, British Patent No. 1,284,649, West German Patent No. 1,1613,76 are used for tone adjustment, color turbidity, and fog prevention.
A so-called Weiss coupler described in No. 9 can be used.

Anionic surfactants are used as dispersion aids when a hydrophobic compound is dissolved in a low boiling point solvent alone or in combination with a high boiling point solvent and dispersed in water using mechanical or ultrasonic waves.
Nonionic surfactants and cationic surfactants can be used.

Between the emulsion layers of the light-sensitive material of the present invention (same color sensitivity, Naruto and/or
or between different color-sensitive layers), color fog prevention agents are used to prevent color turbidity, deterioration of sharpness, and conspicuous graininess due to migration of oxidized form of the main agent or electron transfer agent. can be used.

The color fog preventive agent may be contained in the emulsion layer itself, or
An interlayer may be provided between adjacent emulsion layers and contained in the interlayer.

The silver halide photosensitive material of the present invention can contain an image stabilizer that prevents deterioration of dye images.

The protective layer of the photosensitive material of the present invention, the hydrophilic colloid layer such as the intermediate layer, contains an ultraviolet absorber in order to prevent fogging due to discharge caused by charging of the photosensitive material due to friction, etc., and to prevent image deterioration due to UV light. May contain.

Compounds that change the developability such as development accelerators and development retardants, and bleaching accelerators can be added to the silver halide emulsion layer and/or other hydrophilic colloid layer of the halogenated @photosensitive material of the present invention. Compounds that can be preferably used as development accelerators are listed in Research Disclosure v-(Rese
A compound described in Section XXI B-D of Arch D1closure No. 17643, and the development retardant is:
This is a compound described in Section XXI, Section E of No. 17643. A black and white developing agent and/or its precursor may be used to accelerate development or for other purposes.

The photographic emulsion layer of the silver halide photographic light-sensitive material of the present invention contains polyalkylene oxide or mF2 forms thereof such as ethers, esters, and amines, thioether compounds, and thiomorpholines for the purpose of increasing sensitivity, increasing contrast, or promoting development. , quaternary ammonium compounds, urethane derivatives, urea derivatives, imidazole derivatives, and the like.

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

A matting agent is added to the silver halide emulsion layer and/or other hydrophilic colloid layer of the silver halide photosensitive material of the present invention for the purpose of reducing the gloss of the photosensitive material, improving the ease of writing, and preventing the photosensitive materials from scratching each other. Can be added.

Halogenation of the present invention! ! A lubricant can be added to the photosensitive material to reduce its sliding friction.

Halogenated l! of the present invention! An antistatic agent can be added to the photosensitive material for the purpose of preventing static electricity. The antistatic agent may be used as an antistatic agent on the side of the support on which the emulsion is not laminated.
It may be used in a hydrophilic colloid layer outside the emulsion layer on the side where the emulsion layer is laminated with respect to the emulsion layer and/or the support.

The photographic emulsion layer and/or other hydrophilic colloid layer of the silver halide light-sensitive material of the present invention includes coating properties improvement, antistatic property, sliding property improvement, emulsification dispersion, adhesion prevention, photographic properties (development acceleration, film hardening, etc.). , sensitization, etc.), various surfactants can be used.

Supports used in the silver halide photosensitive material of the present invention include paper laminated with α-olefin polymers (e.g., polyethylene, polypropylene, ethylene/butene copolymer), flexible reflective supports such as synthetic paper, and acetic acid. Included are flexible supports made of semi-synthetic or synthetic polymer films such as cellulose, cellulose nitrate, polystyrene, polyvinyl chloride, polyethylene terephthalate, polycarbonate, polyamide, etc., provided with a reflective layer, glass, metal, ceramics, and the like.

The photosensitive material of the present invention can be used directly or after subjecting the support surface to corona discharge, ultraviolet irradiation, flame treatment, etc., as necessary, or to improve the adhesion, antistatic property, dimensional stability, abrasion resistance, etc. of the support surface. It may be applied through one or more subbing layers to improve hardness, antihalation, frictional properties, and/or other properties.

When coating the silver halide photosensitive material of the present invention during production, a thickener may be used to improve coating properties. or,
For example, in the case of a hardening agent, which is so reactive that it will cause gelation before coating if added to the coating solution in advance, it is preferable to mix it using a static mixer or the like immediately before coating.

In preparing the silver halide photosensitive material of the present invention, the silver halide emulsion layer and other water-based colloid layers were prepared in accordance with Research Disclosure (Research D).
1sclosure) It can be applied by the method described in Section A of No. 17643, XV, and dried by the method described in Section B of the same.

The light-sensitive material of the present invention can be exposed using electromagnetic waves of spectrum J to which the emulsion layer constituting the light-sensitive material of the present invention is sensitive. Light sources include natural light (sunlight), tungsten electric lamps, fluorescent lamps, mercury lamps, xenon arc lamps, carbon arc lamps, xenon flash lamps, shadow tube flying spots, various laser lights, light emitting diode lights, electron beams,
Any light emitted from a phosphor excited by Xil, γ rays, α rays, etc. can be used.

Exposure time ranges from 0.1 seconds to 1 second, which is normally used in printers.
Of course, exposure times shorter than 1 millisecond can be used, such as exposures of 100 nanoseconds to 1 millisecond using a cathode ray tube or xenon flash lamp, and exposure times longer than 1 second are also possible. The exposure may be performed continuously or intermittently.

Various color developments can be used for the development of the photosensitive material of the present invention. Alternatively, a color image may be formed by an inversion method. When the reversal method is used, a black and white negative development step is performed, and a fixing step is performed without white exposure or treatment with a bath containing a fogging agent, followed by color development.

(The processing step of providing white light exposure or the step of processing with a fogging agent may be the same as the color development processing step.) In the present invention, the color development processing step is a step of forming a color image; Specifically, it is a process of forming a color image through a coupling reaction between an oxidized color developing agent and a color coupler.

Therefore, in the color development processing process, it is usually necessary to incorporate a color development agent into the color development solution, but it is necessary to incorporate the color development agent into the color photographic material, and use a color development agent containing the color development agent or a color development agent containing the color development agent. It also includes treatment with an alkaline solution (activator solution). The coloring agent contained in the color developer is aromatic 1v! It is an L-amine color developing agent, and includes aminophenol derivatives and p-phenylenediamine derivatives. These color-producing agents can be used as organic acids and salts of salts, such as hydrochloric acid,! III salt, p-toluenesulfonate, sulfite, oxalate, benzenesulfonate, etc. can be used.

These compounds generally have a concentration of about 0.0.
Concentration of 1 g to 309 ml, more preferably color developer 1
2 is used at a concentration of about 1 g to about 150 g. o,
If the amount added is less than ig, sufficient color density cannot be obtained.

Further, the processing solution temperature of the color developing bath is 10°C to 65°C, more preferably 25°C to 45°C, and most preferably 30°C to
Processed at 40°C.

Examples of the above amine phenol developer include 0-amine phenol, p-amine phenol, 5-amino-phenol,
Included are 2-oxy-toluene, 2-amino-3-oxy-toluene, 2-oxy-3-amino-1,4-dimethyl-benzene, and the like.

A particularly useful primary aromatic amine color developer is N-N'
-Dialkyl-p-phenylenediamine type compound, and the alkyl group and phenyl group may be substituted or unsubstituted. Among them, particularly useful examples include N-N'-dimethyl-p-phenylenediamine hydrochloride, N-methyl-p-phenylenediamine [[, N,N'-dimethyl-p-phenylenediamine hydrochloride, 2- Amino-5-(N-ethyl-N-dodecylamino)-toluene, N-ethyl-N-β-methanesulfonamidoethyl-3-methyl-4-aminoaniline @acid, N-ethyl-N-β- Hydroxyethylaminoaniline, 4-amino-3-methyl-N,N'-diethylaniline, 4-amino-N-(2-methoxyethyl)-N-ethyl-3-methylaniline-1)-)-luenesulfonate etc. can be mentioned.

In addition, the above coloring agent may be used alone or at 2g! The above may be used in combination. Furthermore, the above color developing agents may be incorporated into color photographic materials.

For example, a method of incorporating a color developing agent in the form of a metal salt as described in U.S. Patent No. 3,719,492,
342.559 and Research Disclosure (R
search Q 1 closure ) 1
976 No. 15159, a method of incorporating coloring agent into ship salt, JP-A-58
-135429 and No. 58-24137, etc., or a method of incorporating it as a color developing agent precursor as shown in U.S. Pat. . In this case, use alkaline solution (activator solution) instead of color developer for silver halide color photographic light-sensitive materials! l! X-processing is also possible, and bleach-fixing is performed immediately after the alkali solution treatment. The color developing solution used in the present invention may contain alkaline agents commonly used in developing solutions, such as sodium hydroxide, potassium hydroxide, ammonium hydroxide, sodium carbonate, potassium carbonate, fiA Ft sodium, sodium metaborate, or borax. and various additives such as benzyl alcohol,
It may contain an alkali metal halide such as potassium bromide or potassium chloride, a development regulator such as citradinic acid, and a preservative such as hydroxylamine or sulfite. In addition, various antifoaming agents and surfactants, as well as organic solvents such as methanol, dimethylformamide or dimethyl sulfoxide, and the like can be appropriately contained.

The pH of the color developing solution used in the present invention is usually 7 or more,
Preferably about 9-13, more preferably 95-110
It is.

In addition, the color developing solution used in the present invention may contain antioxidants such as diethylhydroxyamine, tetronic acid, tetronimide, 2-anilinoethanol, dihydroxyacetone, aromatic secondary alcohol, hydroxamic acid, pentose, or hexose, pyrogallol-1,
3-dimethyl ether etc. may be contained.

Various chelating agents can be used as metal ion sequestering agents in the color developing solution used in the present invention. For example, as the chelating agent, an amine polycarbonate such as ethylene/diaminetetraacetic acid, diethylenetriaminopentaacetic acid, etc.
Containing phosphonic acids such as 1-hydroxyethylidene-1,1'-diphosphonic acid, aminotri(methylenephosphonic acid)
or aminopolyphosphonic acid such as ethylenediaminetetraphosphoric acid, oxycarboxylic acid such as citric acid or gluconic acid, phosphonocarboxylic acid such as 2-phosphonobutane-1,2,4-tricarboxylic acid, polyphosphoric acid such as tripolyphosphoric acid or hexametaphosphoric acid. etc., polyhydroxy compounds, etc.

(Effects of the Invention) The halogenated forged photographic light-sensitive material of the present invention has good coloring properties by containing the cyan coupler 3 of the present invention, and furthermore, the formed cyan image is resistant to light and heat. It has excellent robustness.

[Examples] Specific examples of the present invention will be described below, but the embodiments of the present invention are not limited thereto.

Example 1 Silver halide color photographic light-sensitive material samples No. 61 to No. 6 were prepared by sequentially coating the following layers on a paper support laminated on both sides with polyethylene from the support side.

B1...-1,29/f gelatin, 0.32 (
Blue-sensitive silver chlorobromide emulsion of 1/f (in terms of silver, the same applies hereinafter) (
layer containing 0.8 h/l' of yellow coupler (Y-1) dissolved in 0.50 g/f of dioctyl phthalate (silver chloride content 98 mol%).

Layer 2...0.70 g/v' gelatin, 810
/f irradiation dyed Fl (AI-1) and 4mt
Intermediate layer consisting of (AI-2) of r/f.

Layer 3...-1.25 CI/l' gelatin, 0.
200/f green-sensitive silver chlorobromide emulsion (silver chloride content 97
mol%), 0,30 (0,62 g/12 magenta coupler (M-
A layer containing 1).

Layer 4: Intermediate layer made of gelatin of 1.201 J/f.

F! J 5--...--1, 20M t'' gelatin, 0.30Cl/117) red-sensitive silver chlorobromide emulsion (arsenic salt content 96 mol%), 0.200/f dioctyl phthalate A layer containing a dissolved cyan coupler shown in Table-1 of 0.45 (J/f).

Layer 6 --- 1.00+7/r gelatin and 0.
0 dissolved in dioctyl phthalate of 20(]/v'
, a layer containing 30 g/f of ultraviolet absorber (UV-1).

Layer 7: A layer containing gelatin of 0.50 (1/f).

Margin below (Y-1) t (M-1) c.

t Comparative coupler t (Coupler described in JP-A-59-166956) (AI
-1) (AI-2) (UV-1) CsHo(t) Note that sodium 2,4-dichloro-6-hydroxy-s-triazine was added as a hardening agent in layers 2.4 and 7.
Each was added in an amount of 0.017 g per 1 g of gelatin.

Each of the above photosensitive material samples Nos. 61 to 6 was exposed through an optical wedge and then processed in the following steps.

Processing steps (35°C) Color development: 45 seconds bleach-fixing 45 seconds stabilization 1 minute 30 seconds drying 60-80°C 2 minutes The composition of each processing solution is as follows.

[Color developer pure water 800i, c triethanolamine 11.12N, N-
Diethylhydroxylamine (85% aqueous solution) 61!2 Potassium chloride 2.3g Potassium sulfite 0.3g Potassium carbonate
30 Sodium cutitrapolyphosphate 2.0Q N-ethyl-N-β-methanesulfonamidoethyl-3-ethyl-4-amine aniline sulfate 529 Add pure water to make 12, 20% potassium hydroxide or 10% dilute sulfuric acid Adjust to p) (= 10.1.

[Bleach-fix solution] Pure water 8001g Iron (III) ethylenediaminetetraacetate Ammonium 65゜Sodium acetate 5g Ammonium thiogate 60 (1 Sodium hydrogen sulfite 109 Sodium metabisulfite 2 g Sodium chloride
Add 10 g of pure water to make 12, and adjust to DH = 5.6 with V8 sulfuric acid.

[Stabilizing liquid] 5-chloro-2-methyl-4-isothiazolin-3-one 1.0 gl-human O-oxyethylidene-1.1-diphosphonic acid 2. Add OO pure water to make 12, and make DH= with sulfuric acid or water M1 Hypotassium.
Adjust to 7.0.

Sensitometry was performed on each sample after the above treatment, and the maximum density (Dm') and sensitivity (S) of the red-sensitive emulsion layer were measured.
) was sought.

Furthermore, each of the above-mentioned treated samples was irradiated with a xenon fade meter for 5 days to examine the light resistance of the cyan image.

In addition, each of the above-mentioned processed samples was stored for 2 weeks under high temperature and high humidity at 80''C and 90% RH to examine the storage stability of the cyan image.

The results are shown in Table 1 below.

As is clear from Table 1 above, samples No. 4, 5 and 6 of the present invention using the cyan coupler according to the present invention are different from sample No. 1 using a conventionally known cyan coupler.
Compared to No. 2 and No. 3, it is superior in all aspects of sensitivity, maximum density, light resistance, and image storage stability.

Patent applicant: Roku Konishi Photo Industry Co., Ltd. Procedural amendment August 11, 1985 Commissioner of the Patent Office Mr. Michibe Uga Ro1, Description of the case 1986 Patent #R No. 141780 No. 2, Name of the invention Novel cyan dye Silver halide photographic light-sensitive material containing a forming coupler 3, relationship with the amended person case Patent applicant address 1-26-2 Nishi-Shinjuku, Shinjuku-ku, Tokyo Name (1)
27) Benko Konishiroku Photo Industry Co., Ltd. Representative Director
Keio 4, Agent 102 Address: Kudan-Rosaka Building, 4-1-1 Kudankita, Chiyoda-ku, Tokyo Telephone: 263-9524 (1) Listed at the end of page 5 of Akira ``... Dodecyl groups etc. Insert the following sentence between "." and "Kiru," in the first line of page 6.

(b) In the above general formula [I], the aryl group represented by R2 includes a phenyl group, a naphthyl group, etc., but a phenyl group is preferable.

These aryl groups include those having substituents, and there may be two or more substituents. Examples of substituents include halogen atoms, alkyl groups, aryl N, and pK
Examples include dissociative groups in which a is 6 to 12 and substituents containing these dissociative groups. Specifically, in addition to the above-mentioned halogen atoms and alkyl groups, for example, hydroxyl groups, sulfonyl groups, sulfonamide groups, etc. can be mentioned.

Here, examples of the halogen atom include a chlorine atom, a bromine atom, etc., and a chlorine atom is particularly preferred. Examples of alkyl groups include methyl group, ethyl group, i-
Examples include propyl group, t-butyl group, t-pentyl group, pentadecyl group, etc., and these alkyl groups may further have a substituent.

Examples of the sulfonyl group include alkylsulfonyl groups such as a methylsulfonyl group, and arylsulfonyl groups such as a phenylsulfonyl group. Examples of the sulfonamide group include alkylsulfonamide groups such as butylsulfonylamine group and dodecylsulfonylamino group, arylsulfonamide groups such as benzenesulfonamide group, p-toluenesulfonamide group, and dodecylbenzenesulfonamide group, dimethyl Examples include alkylaminosulfonamide groups such as aminosulfonamide groups.

In the general formula [I], the alkyl group having 4 or less carbon atoms represented by R3 includes, for example, a methyl group, an ethyl group, an n-propyl group, an n-butyl group, and the like.

In the general formula [I], examples of the group capable of performing JIHI by coupling with an oxidized product of a developing agent represented by X include a halogen atom (specifically, each atom such as chlorine, bromine, and fluorine), an oxygen atom, Alternatively, examples include aryloxy groups, carbamoyloxy groups, carbamoylmethoxy groups, acyloxy groups, sulfonamide groups, succinimide groups, etc. in which a nitrogen atom is directly bonded to the coupling position.(2) Specification No. 13 Page 1st line to specification 14th
On the last line of the page, "In the general formula [I],...
``...by mentioning imide groups, etc.'' is deleted.

Two more

Claims (1)

[Scope of Claims] In a silver halide photographic material having at least one silver halide emulsion layer on a support, at least one of the silver halide emulsion layers is a cyan compound represented by the following general formula [I]. A silver halide photographic material containing a dye-forming coupler. General formula [I] ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (In the formula, R^1 represents an alkylene group, R^2 represents an aryl group, and R^3 represents an alkyl group having 4 or less carbon atoms. and X represents a hydrogen atom or a group that can be separated by coupling with an oxidized form of a developing agent.)