JPH0451149A - Silver halide color photographic sensitive material - Google Patents

Abstract

PURPOSE:To obtain high coupling reactivity and high dye absorption densities by incorporating specific cyan dye forming couplers into the above photosensitive material. CONSTITUTION:The silver halide color photographic sensitive material having silver halide emulsion layers on the base contains at least one kind of the cyan dye forming couplers expressed by formula I or II. In the formulas I, II, R<1> denotes an alkyl group; R<2> is synonym with R<1> or denotes a hydrogen atom, etc.; Q denotes the nonmetal atom necessary for forming an alicyclic or heterocyclic ring consisting of a single ring to 4 rings respectively including 4 to 7C in the rings; Ar denotes an aryl group, etc.; Z denotes a hydrogen atom or the group which can be eliminated by the coupling reaction with the oxidant of an arom. primary amine developing agent. The high coupling reactivity of the cyan couplers and the high color developing densities of the images are obtd.

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 novel phenolic cyan dye-forming coupler.

(Prior art) When a silver halide photographic light-sensitive material is exposed to light and then subjected to color development, an oxidized aromatic-grade amine developer and a dye-forming coupler (hereinafter referred to as coupler) react to form a color image. rub Generally, in this method, a subtractive color reproduction method is used, and in order to reproduce blue, green, and red, images of yellow, magenta, and cyan, which are complementary colors, are formed, respectively. Phenol derivatives or naphthol derivatives are often used as couplers to form cyan-colored images. In color photography, color-forming couplers are added to the developer, or added to the light-sensitive photographic emulsion layer, or It is incorporated in other color image forming layers and forms a non-diffusible dye by reacting with the oxidized product of the color developer formed by development.

The reaction between the coupler and the color developing agent takes place at the active site of the coupler, and a coupler having a hydrogen atom at the active site is a 4-equivalent coupler, i.e. stoichiometrically requires 4 moles of development to form 1 mole of dye. It requires silver halide with a nucleus.

On the other hand, those having a group that can leave as an anion at the active site are 2-equivalent couplers, that is, couplers that stoichiometrically require only 2 moles of silver halide having a development nucleus to form 1 mole of dye. Therefore, compared to a 4-equivalent coupler, the amount of silver halide in the photosensitive layer can be generally reduced and the film thickness can be made thinner, making it possible to shorten the processing time of the photosensitive material and further improving the sharpness of the color image formed. improves.

By the way, among cyan couplers, naphthol type couplers are used because the absorption of the generated dye image is at a sufficiently long wavelength and there is little overlap with the absorption of the magenta dye image, and the coupling reactivity with the oxidized form of the color developer is low. Since it can be selected up to high prices, it has been widely used for photographic purposes, mainly color negative films. However, dye images obtained from naphthol-type couplers tend to be reduced and faded by divalent iron ions that accumulate in tired bleach or bleach-fix baths (referred to as reductive fading), and their heat fastness is poor. , improvements were strongly desired.

On the other hand, U.S. Patent No. 4,333.999 describes a p-cyanophenylureido group at the 2-position and a ballast group at the 5-position (
A phenol type cyan coupler having a carbonamide group which is a diffusion resistance imparting group) is disclosed. These couplers undergo a bathochromic shift when the dyes associate in the film, giving dye images with excellent hue, and are also excellent in fastness, so they are widely used as couplers to replace the naphthol-type cyan couplers. It's starting to happen.

Also, Japanese Patent Publication No. 63-11656 and Japanese Patent Publication No. 63-16
No. 1451 discloses a phenolic cyan coupler having a substituted aryl ureido group at the 2-position and a substituted or unsubstituted (substituted α-sulfonyl)alkanoylamino group at the 5-position.

According to the specification, these couplers provide high coupling reactivity and good absorption with narrow half-width.

However, these couplers often have poor emulsion stability and color increase under thermal conditions (color increase refers to a phenomenon in which color density increases with the passage of time after development processing). I have problems such as.

(Problems to be Solved by the Invention) In recent years, high performance has continued to be demanded of photographic materials. Therefore, higher coupling reactivity and higher dye absorption density are required for the conventional couplers as well.

There is also a strong desire to improve the stability of emulsions and to solve the problems of suppressing staining and color increase under thermal conditions when these couplers are used.

Therefore, an object of the present invention is to provide a silver halide color photographic light-sensitive material containing a cyan coupler that provides high coupling reactivity and high dye absorption density, has excellent emulsion stability, and exhibits little color increase under thermal conditions. It is in.

(Means for Solving the Problems) As a result of extensive research in order to achieve the above-mentioned problems, the present inventors have found that the problems can be achieved in the following silver halide color photographic light-sensitive materials.

In a silver halide color photographic light-sensitive material having a small number of silver halide emulsion layers on a support, at least one cyan dye-forming coupler represented by the following general formula (I-a) or (I-b) is used. A silver halide color photographic material characterized by containing.

General formula (I-a) General formula (I-b) (wherein, R1 represents an alkyl group, alkenyl group, cycloalkyl group, aryl group, heterocyclic group, alkoxy group, aryloxy group, or amino group, R2 is the same as R', or represents a hydrogen atom, an acyl group, or an alkoxycarbonyl group, and Q is a monocyclic ring containing 4 to 7 atoms in the ring together with the carbon atom to which R' So□- is bonded. A nonmetallic atom necessary to form an alicyclic or heterocyclic ring consisting of a ring, A nonmetallic atom necessary to form an alicyclic or heterocyclic ring consisting of ~4 rings, Ar represents an aryl group or a heterocyclic group,
Z represents a hydrogen atom or a group capable of being separated by a coupling reaction with an oxidized product of an aromatic primary amine developer. ) In the present invention, the groups R'-R", Q, X and Ar are not only unsubstituted (but also include those having substituents).

The cyan coupler represented by general formula (I) will be explained in detail below. In the general formula (I), R' is a linear or branched alkyl group having a total number of carbon atoms (hereinafter referred to as C number) of 1 to 36 (more preferably 6 to 24), C
A linear or branched alkenyl group having 2 to 36 carbon atoms (more preferably 6 to 24 carbon atoms), a 3 to 12-membered cycloalkyl group having 3 to 36 carbon atoms (more preferably 6 to 24 carbon atoms), and a 3- to 12-membered cycloalkyl group having 6 to 36 carbon atoms.
~36 (more preferably 6 to 24) aryl group, C1 to 36 (more preferably 1 to 24) heterocyclic group, C
an alkoxy group having 1 to 36 carbon atoms (more preferably 1 to 24), an aryloxy group having 6 to 36 carbon atoms (more preferably 6 to 24 carbon atoms), or an aryloxy group having 1 to 36 carbon atoms (more preferably 1 to 24 carbon atoms);
), and these represent substituents (e.g. halogen atoms, hydroxyl groups, carboxyl groups, sulfo groups,
Cyano group, nitro group, amino group, alkyl group, alkenyl group, alkynyl group, cycloalkyl group, aryl group,
Alkoxy group, aryloxy group, alkylthio group, arylthio group, alkylsulfonyl group, arylsulfonyl group, acyl group, acyloxy group, alkoxycarbonyl group, aryloxycarbonyl group, carbonamide group, sulfonamide group, carbamoyl group, sulfamoyl group, It may be substituted with a ureido group, an alkoxycarbonylamino group, a sulfamoylamino group, an alkoxysulfonyl group, an imido group, a carbonyl group, or a heterocyclic group (hereinafter referred to as substituent group A).

R' is preferably linear, branched, or a substituent (alkoxy group, alkylthio group, aryloxy group, arylthio group, alkylsulfonyl group, arylsulfonyl group, aryl group, alkoxycarbonyl group, epoxy group, cyano group, or a halogen atom) [e.g. n-octyl, n-decyl, n-dodecyl,
n-hexabcyl, 2-ethylhexyl, 3,5.5-
Trimethylhexyl, 2-ethyl-4-methylpentyl, 2-hexyldecyl, 2-hebutylundecyl, 2-
Octyldodecyl, 2,4.6-1-dimethylheptyl, 2,4,6.8-tetramethylnonyl, benzyl, 2
-Phenethyl, 3-(O-octylphenoxy)propyl, 3-(2,4-di-t-pentylphenoxy)propyl, 2-(4-biphenyloxy)ethyl, 3-dodecyloxypropyl, 2-dodecylthio Ethyl, 9゜IO-epoxyoctadecyl, dodecyloxycarbonylmethyl, 2-(2-naphthyloxy)ethyl 1, unsubstituted or substituted (e.g. halogen atom, aryl group,
an unsubstituted or substituted group (halogen atom, alkyl group, cycloalkyl group, aryl group, alkoxy group or aryloxy group)
cycloalkyl group [e.g. cyclopentyl, cyclohexyl, 3,5-dimethylcyclohexyl, 4-
t-Butylcyclohexylco, unsubstituted or substituted (
Aryl groups (e.g., phenyl, 4-dodecyloxyphenyl, 4-
biphenylyl, 4-dodecanesulfonamidophenyl,
4-t-octylphenyl, 3-pentadecylphenyl], unsubstituted or hetero having a substituent (halogen atom, alkyl group, alkoxy group, alkoxycarbonyl group, aryl group, carbonamide group, alkylthio group or sulfonamide group) cyclic group [e.g., 2-pyridyl,
2-benzothiazolyl, 5-tetrazolyl], unsubstituted or substituted groups (alkoxy group, alkylthio group, aryloxy group, arylthio group, alkylsulfonyl group,
an alkoxy group having an arylsulfonyl group, an aryl group, an alkoxycarbonyl group, an epoxy group, a cyano group, or a halogen atom [e.g., n-octyloxy, n
-decyloxy, n-dodecyloxy, n-hexadecyloxy, 2-ethylhexyloxy, 3.5.5-trimethylhexyloxy, 2-ethyl-4-methylpentyloxy, 2-hexyldecyloxy, 2- Butylundecyloxy, 2-octyldodecyloxy, 2,
4.6-trimethylhebutyloxy, 2,4,6.8-
Tetramethylnonyloxy, benzyloxy, 2-phenethyloxy, 3-(t-octylphenoxy)propoxy, 3-(2,4-di-t-pentylphenoxy)
propoxy, 2-(4-biphenyloxy)ethoxy,
3-dodecyloxypropoxy, 2-dodecylthioethoxy, 9.10-epoxyoctadecyloxy, dodecyloxycarbonylmethoxy, 2-(2-naphthyloxy)ethoxy], unsubstituted or substituted (halogen atom, alkyl group, alkoxy group) , alkoxycarbonyl group, aryl group, carbonamide group, alkylthio group or sulfonamide group) [e.g. phenoxy, 4-dodecyloxyphenoxy, 4-phenylphenoxy, 4-dodecanesulfonamidophenoxy, 4-t- octylphenoxy, 3-pentadecylphenoxy] or unsubstituted or substituted groups (alkoxy group, alkylthio group, aryloxy group, arylthio group, alkylsulfonyl group, arylsulfonyl group, aryl group, alkoxycarbonyl group, epoxy group, cyano group or an amino group having a halogen atom [e.g.
To n-octylamino, di-n-octylamino, n-decylamino, n-dodecylamino, n-hexadecylamino, 2-ethylhexylamino, di-2-ethylhexylamino, 3,5.5-1-dimethyl xylamino, 2-ethyl-4-methylpentylamino, 2-hexyldecylamino, 2-hebutylundecylamino, 2-
Octyldodecylamino, 2.4.6-trimethylhebutylamino, 2゜4.6.8-tetramethylnonylamino, pendylamino, dibendylamino, 2-phenethylamino, 3-(t-octylphenoxy)propylamino, 3- (2,4-di-t-pentylphenoxy)
Propylamino, 2-(4-biphenyloxy)ethylamino, 3-dodecyloxypropylamino, 2-dodecylthioethylamino, 9゜10-epoxyoctadecylamino, dodecyloxycarbonylmethylamino, 2
-(2-naphthyloxy)ethylamino, phenylamino, diphenylamino, 4-dodecyloxyphenylamino, 4-phenylphenylamino 1,4-dodecanesulfonamidophenylamino, 4-t-octylphenylamino, 3-pentadecyl phenylamino],
Particularly preferably, the linear, branched or substituted alkyl group, unsubstituted or substituted aryl group,
It is an alkoxy group, an aryloxy group or an amino group.

- In formula (I), R2 has the same definition as R1, and also has a hydrogen atom, a C number of 2 to 36 (more preferably 2 to 2
4) acyl group or C number 2 to 36 (more preferably 2
~24) represents an alkoxycarbonyl group, which may be substituted with substituent group A, and R'' may be different from or the same as R1.

R1 preferably has the same meaning as R1, and also includes a hydrogen atom, an unsubstituted or substituent group (e.g., a halogen atom, an alkyl group, a cycloalkyl group, an alkenyl group, an aryl group, a heterocyclic group, an alkoxy group, an aryloxy group, an alkylthio group) , arylthio group, alkoxycarbonyl group or aryloxycarbonyl group) [e.g., acetyl, pivaloyl, trifluoroacetyl],
or an alkoxycarbonyl group that is unsubstituted or has a substituent (halogen atom, alkyl group, alkoxy group, aryl group, cycloalkyl group, alkenyl group or alkylthio group) [e.g. methoxycarbonyl, t-butoxycarbonyl, trifluoromethoxycarbonyl] Particularly preferred are a hydrogen atom, the aforementioned linear, branched or substituted alkyl group, or an unsubstituted or substituted aryl group.

In general formula (I), Q is R' So, a monocyclic ring containing 4 to 7 ring atoms, together with the carbon atom to which - is bonded.
Represents a nonmetallic atom necessary to form an alicyclic or heterocyclic ring consisting of 4 rings, and the ring may have an unsaturated bond or be substituted with the above substituent group A. good.

Q is preferably sufficient carbon, oxygen, sulfur or nitrogen atoms to form a 5-, 6- or 7-membered ring together with the carbon atom to which R' So, - is attached.

Particularly preferably, Q is a cyclohexyl ring, a cyclopentyl ring, a cyclobutyl ring, a cyclohebutyl ring, a γ-lactone ring, a δ-
Forms a lactone ring, γ-lactam ring, δ-lactam ring, piperidine ring, pyrrolidine ring, tetrahydrofuran ring, tetrahydroxane ring, thiolane ring, thiane ring, piperidine ring, sulfolane ring, morpholine ring or 1,3-dithiane ring sufficient carbon, oxygen, sulfur or nitrogen atoms to

In general formula (I), X is a monocyclic ring each containing 4 to 7 ring atoms together with the carbon atom to which R8 is bonded and 808.
Represents a nonmetallic atom necessary to form an alicyclic or heterocyclic ring consisting of 4 rings, and the ring may have an unsaturated bond or be substituted with the above substituent group A. good.

X is preferably sufficient carbon, oxygen, sulfur or nitrogen atoms to form a 4-, 5-, 6- or 7-membered ring with the carbon atom to which R2 is attached and 802 .

X is particularly preferably carbon, oxygen, sulfur or nitrogen atoms sufficient to form a 5-, 6- or 7-membered ring together with the carbon atom to which R8 is bonded and So snow.

In the general formula (I), Ar preferably has 6 to 36 carbon atoms,
More preferably, it represents an aryl group of 6 to 15, and may be substituted with a substituent selected from the above substituent group A, or may be a fused ring. Here, as a preferable substituent, a halogen atom (F, CX, Br, engineering), cyano group, nitro group, acyl group (e.g. acetyl, benzoyl), alkyl group (e.g. methyl, t-butyl, trifluoromethyl, trichloromethyl), alkoxy group (e.g. methoxy, ethoxy, butoxy, trifluoromethoxy), alkylsulfonyl groups (e.g. methylsulfonyl, propylsulfonyl, butylsulfonyl, benzylsulfonyl)
, arylsulfonyl groups (e.g. phenylsulfonyl,
(ri-)-lylsulfonyl, p-chlorophenylsulfonyl), alkoxycarbonyl groups (e.g. methoxycarbonyl, butoxycarbonyl), sulfonamide groups (e.g. methanesulfonamide, trifluoromethanesulfonamide, toluenesulfonamide), carbamoyl groups (
e.g. N,N-dimethylcarbamoyl, N-phenylcarbamoyl) or sulfamoyl groups (e.g. N,N-
diethylsulfamoyl, N-phenylsulfamoyl). Ar is preferably a phenyl group having at least one substituent selected from a halogen atom, a cyano group, a sulfonamide group, an alkylsulfonyl group, an arylsulfonyl group, and a trifluoromethyl group, and more preferably 4-cyanophenyl. , 4-cyano-
3-halogenophenyl, 3-cyano-4-halogenophenyl, 4-alkylsulfonylphenyl, 4-alkylsulfonyl-3-halogenophenyl, 4-alkylsulfonyl-3-alkoxyphenyl, 3-alkoxy-4
-alkylsulfonylphenyl, 3,4-dihalogenophenyl, 4-halogenophenyl, 3.4.5-trihalogenophenyl, -3,4-dicyanophenyl, 3-cyano-4,5-dihalogenophenyl, 4- Trifluoromethylphenyl or 3-sulfonamidophenyl, particularly preferably 4-cyanophenyl, 3-cyano-4
-halogenophenyl, 4-cyano-3-halogenophenyl, 3,4-dicyanophenyl or 4-alkylsulfonylphenyl.

In the general formula (T), 2 represents a hydrogen atom or a coupling-off group (including H deatomization; the same applies hereinafter); a preferred example of a coupling-off group, a halogen atom, -
OR", -SR"-0CR", -0SO,R",
-NHCOR" general formula (If) A C6-30 arylazo group, a C1-30 heterocyclic group (e.g. succinimide , phthalimide, hydantoinyl, pyrazolyl, 2-benzotriazolyl), etc. Here, R1 is an alkyl group having 1 to 36 carbon atoms, an alkenyl group having 2 to 36 carbon atoms, or an alkenyl group having 3 to 3 carbon atoms.
6 cycloalkyl group, C6-36 aryl group, or C2-36 heterocyclic group, these groups may be substituted with a substituent selected from Group A, and Z further represents Preferably a hydrogen atom, a halogen atom, an alkoxy group, an aryloxy group or an alkylthio group, particularly preferably a hydrogen atom, a chlorine atom, and the following general formula (II)
or a group represented by the following general formula (m).

(In the formula, R4 is a halogen atom, a cyano group, a nitro group, an alkyl group, an alkoxy group, an alkylthio group, an alkylsulfonyl group, an arylsulfonyl group, a carbonamide group, a sulfonamide group, an alkoxycarbonyl group, a carbamoyl group, a sulfamoyl group, or carboxyl group,
m represents an integer from 0 to 5. Here, when m is plural, R4
may be the same or different, ) General formula (III) 1] -P-, R7 and R8 are each a hydroxyl group, an alkyl group, an aryl group, an alkoxy group, an alkenyloxy group, an aryloxy group or a substituted or An unsubstituted amino group, n represents an integer of 1 to 6. Here, when n is plural, (C) may be the same or different. ) In the general formula (n), R4 is preferably a halogen atom, an alkyl group (e.g. methyl, t-butyl, t-octyl, pentadecyl), an alkoxy group (e.g. methoxy,
n-butoxy, n-octyloxy, benzyloxy,
methoxyethoxy), carbonamide groups (e.g. acetamide, 3-carboxypropanamide) or sulfonamide groups (e.g. methanesulfonamide, toluenesulfonamide, p-dodecyloxybenzenesulfonamide), particularly preferably alkyl or alkoxy groups. It is. m is preferably an integer of 0 to 2, more preferably O or 1.

In general formula (III), when R5 and/or R6 represent a monovalent group, preferably an alkyl group (e.g. methyl, ethyl, n-butyl, ethoxycarbonylmethyl, benzyl, n-decyl, n-dodecyl), Aryl groups (e.g. phenyl, 4-chlorophenyl, 4-methoxyphenyl), acyl groups (e.g. acetyl, decanoyl,
benzoyl, pivaloyl) or carbamoyl group (e.g. N-ethylcarbamoyl, N-phenylcarbamoyl), and R' and R6 are more preferably a hydrogen atom,
It is an alkyl group or an aryl group. General formula (II)
In, R7 is preferably an alkyl group, an alkoxy group,
It is an alkenyloxy group, an aryloxy group, or a substituted or unsubstituted amino group, and more preferably an alkoxy group or a substituted or unsubstituted amine group.

In general formula (III), n preferably represents an integer of 1 to 3, more preferably 1.

Specific examples of R1 in general formula (1) are shown below.

CI(3, C2H5* C3H7(n, -C4H9(5), C5H,, (nl, C6Hl3(nl+ H2 C4Hgft) -C8H,7 wholesale, CloH21(nl+ C12825-- Cl4H29 wholesale, Cl6H33(5), Cl8H37( 6)) CH2(CF2CF2)2H CH2 C4Hg(tl NHCH3 -NHC2H5 NHC3H7 round, 10CH2(CF2CF2)2H H2 C4H9ftl CH3 CH3 NHCH2cH2CHCH2C4H9(tl, N HC
HC16R21 (nl, specific examples of R2 in general formula (I) are shown below.

-H.

CH3 C2H3 -C3H7(c)1 -C4H8 wholesale, C3H11(rj% -C6H13(nl　1 C8HI70, -C10H21■1 CI2H2S■1 C14lC14H2% -C16H33 (5), Cl8H37■1 NHCH2(CF2CF2)2H H2 C4H9ftl In general formula (I) below, ■ H3 less than General 2 m) K May X Below is the general formula (1) An example of Z in is shown.

0CCII.

0SO□C113 Below is the general formula (1) An example of Ar in is shown.

10CII□CHzOC1!3 -OCH,C00CH3 0(JIzCHzCOOClh OCtlCOOCl(3 CHl OCIbCOOI+ 0C11□C11fSo□C11゜0CIlzCONIICHzCIIzOH-O CII□
C0NHCII□CH,0C)13-OCJICOOC
ZIIS OC82C1+□011 CHzCOOCdls OCtlzCHzSCIlzCOOIIOC11□CI
l□Nll5OzCII: +5CH2COO11 -5CII□CIl□C00H -5CHCOO11 -3CII□cozo++ CI+3 Note that when 2 is a coupling-off group, it is preferable that it does not contain a photographically useful group (e.g. development inhibitor residue, dye residue) .

Specific examples of the cyan coupler represented by the general formula (I) are shown below, but the invention is not limited thereto.

Cl1zC1l□C00I+ 0CHzCOOCallq C,, H23CONHsha SO21 0C112COOC4119 \ , CHζ CH2CH2 CH3 H3 H2 / , - The cyan coupler of the present invention represented by formula (I) can be synthesized by various synthetic routes. , below are representative This shows a synthetic route.

Carboxylic acid a is reacted with bromine to induce a-bromo acid bromide b. At this time, the reaction proceeds smoothly if red phosphorus or chlorosulfonic acid is used as a catalyst. The reaction temperature is usually 0 to 100"C, preferably 30 to 100C.

When b is reacted with ethanol, ethyl ester C is instantly formed.
generate.

Compound d can be obtained by reacting C with a mercaptan in the presence of a base. Although the reaction solvent does not need to be used, it may be used. As a solvent, methanol,
Solvents such as ethanol, isopropyl alcohol, ethyl acetate, acetonitrile, toluene, tetrahydrofuran, dioxane, N,N-dimethylformamide, N,N-dimethylacetamide, methylene chloride, and chloroform may be used. When the following induction from d to e is carried out all at once in the reaction system, the reaction solvent is preferably methanol, ethanol, isopropyl alcohol, or the like. In reactions C to d, a base may be used. As the base, potassium carbonate, sodium carbonate, sodium hydroxide, potassium hydroxide, pyridine, p-dimethylaminopyridine,
Examples include DABCO (diazabicyclooctane), triethylamine, N-methylmorpholine, DBU (diazabicycloundecene), and DBN (diazabicyclononene). The reaction temperature is -50 to 250°C, preferably 0 to 200°C.

It is common to use an aqueous solution of an inorganic base such as a lithium aqueous solution, a potassium hydroxide aqueous solution, or a sodium carbonate aqueous solution. As a reaction solvent, water, methanol, ethanol,
A water-miscible solvent such as isopropyl alcohol, tetrahydrofuran, etc. is chosen. Reaction temperature is usually -20~100℃
, preferably 0 to 90°C.

Induction from b to C can be carried out using hydrogen peroxide, sodium metaperiodate, m-chloroperbenzoic acid, monoperoxyphthalic acid magnesium salt hexahydrate, performic acid, peracetic acid, trifluoroperacetic acid, permanganese. Acid salts, chromic acid, ruthenium tetroxide, ozone, anodic oxidation, hydrogen peroxide/sodium tungstate, etc. are used. As the solvent, acetic acid, methylene chloride, chloroform, carbon tetrachloride, methanol, ethanol, impropatol, t-butanol, etc. are used. The reaction temperature is usually -30 to 200°C, preferably -20 to 80°C.

f to g can be induced using thionyl chloride, phosphorus oxychloride, phosphorus pentachloride, oxalyl chloride, etc. without solvent or
Methylene chloride, chloroform, carbon tetrachloride, dichloroethane, toluene, N,N-dimethylformamide, N,
The reaction is carried out in a solvent such as N-dimethylacetamide. The reaction temperature is usually -20 to 150°C, preferably -10 to 80°C.

Compounds are disclosed in U.S. Patent No. 4,333,999 and JP-A-6
No. 0-35731, No. 61-2757, No. 61-42
It can be synthesized by the synthesis methods described in No. 658 and Japanese Patent Application Laid-Open No. 63-208562.

The reaction between g and h can be carried out without a solvent or with acetonitrile, ethyl acetate, tetrahydrofuran, dioxane, N,N-dimethylformamide, N,N-dimethylacetamide, N
, N'-dimethylimidacylin-2-one, etc., at a temperature range of usually -20 to 150°C, preferably -10 to 80°C. At this time, a weak base such as pyridine, imidazole, N,N-dimethylaniline, etc. may be used. - The cyan coupler expressed by formula (I) is f and h
It can also be synthesized by direct dehydration condensation reaction with N,N'-dicyclohexyl sulfodiimide, carbonyldiimidazole, etc. as the condensing agent.

Synthesis Example 1 Synthesis of Exemplified Compound 31 Cyclohexylcarboxylic acid (36.5g) under a nitrogen stream.

0.285mol), red phosphorus (0.88g, 0.0
bromine (95.8g, 0.599mol)
) was added dropwise at room temperature over 1 hour, and heated at 60°C for 3 hours. After cooling, it is added to a stirred ethanol (500 m[I) solution at 0°C and stirred for 15 minutes. When the solvent was distilled off under reduced pressure, ethyl α-bromocyclohexanecarboxylate (
61.9 g, 88%) was obtained. This ethanol (
Hexadecyl mercaptan (68.0 g) was added to a 300 TIlil solution under a nitrogen stream.

0.2640101), sodium hydroxide (lo, 6
20 ml of an aqueous solution of 0.265 mol) was added thereto, and the mixture was heated under reflux for 3 hours. After cooling, add tetrahydrofuran (100
ml), sodium hydroxide (21.2g, 0.5
30 mol) and stirred for 2 hours.

Add dilute hydrochloric acid and extract three times with ethyl acetate to obtain α-hexadecylthiocyclohexanecarboxylic acid (45.4 g,
45%) is obtained. This carboxylic acid (38.4 g.

Sodium tungstate (1 g) was added to acetic acid (500 d) solution of 0.10 mol), and 35% hydrogen peroxide solution (2
2.6cc.

0.22 mol) was added dropwise over 1 hour. The reaction was carried out at 70°C for 2 hours, and after cooling, water was added and the mixture was extracted three times with ethyl acetate. The organic layer is washed with an aqueous sodium hydrogen carbonate solution, dilute hydrochloric acid, water and saturated brine, and dried over anhydrous sodium sulfate.

The solvent was distilled off under reduced pressure to obtain α-hexadecanesulfonylcyclohexanecarboxylic acid (36.0 g, 87%).

To a methylene chloride solution of this carboxylic acid (1 g, Og, 0.043 mol) was added N,N-dimethylformamide (lcc) and oxalyl chloride (9 cc) at room temperature.
Add and stir for 1 hour. The solvent was distilled off under reduced pressure to obtain a crude product of α-hexadecanesulfonylcyclohexanecarboxylic acid chloride.

5-Amino-2-(3-(4-cyanophenyl)ureido)phenol (11.5 g, 0.04
3 mol) of N,N-dimethylacetamide (200T
The above crude product of carboxylic acid chloride is added dropwise to the solution (rlil) at room temperature over 10 minutes, and the mixture is stirred for 2 hours. After cooling, add water and extract twice with ethyl acetate. organic layer to 0
．． Wash with 1N diluted hydrochloric acid, water, and saturated saline, and dry with anhydrous sodium sulfate.

The solvent was distilled off under reduced pressure, and the residue was diluted with hexane:ethyl acetate=3
When recrystallized from 0:1, Exemplified Compound 31 (19.0 g,
66%) was obtained.

In the present invention, the coupler solvents listed below can be used, but for cyan couplers, phthalate esters 8 (e.g. dibutyl phthalate, di-2-ethylhexyl phthalate, didodecylphthalate, ethyl phthalyl ethyl glycolate) etc.), fatty acid esters (e.g. 2-ethylhexyl tetradecanoate, di-2-ethylhexyl adipate, di-2-ethylhexyl sebacate, 2-ethylhexyl, 9.1O-epoxystearate), benzoic acid esters (e.g. -ethylhexylbenzoate, dedosylbenzoate, hexadecyl-4-hydroxybenzoate, etc.), phenols (e.g., 2.4-di-t-pentylphenol, 2.
High boiling point organic solvents such as 4-dinonylphenol, 2,4-didodecylphenol, etc.) and chlorinated paraffins (for example, paraffins with a chlorine content of 40 to 70% by weight) are preferred.

The cyan coupler of the present invention can be used in any layer, including a photosensitive emulsion layer, a non-photosensitive emulsion layer, and an intermediate layer.
It is preferably added to the light-sensitive emulsion layer, and more preferably added to the red-sensitive emulsion layer.

The cyan coupler of the present invention may be used alone as a cyan coupler, or may be used in combination with other cyan couplers. Preferred cyan couplers that can be used in combination include 1-naphthol type cyan coupler and 5-amido-1-naphthol type cyan coupler (US Pat. No. 690
899, described in JP-A-64-78252), 2-ureidophenol type cyan coupler (JP-A-64-20)
No. 44).

The coupler of the present invention can be used, for example, in color paper, color reversal paper, color positive film, color negative film,
Color reversal film, color can be directly applied to positive photosensitive materials. Application to color negative film is particularly preferred.

The cyan coupler of the present invention can be added to the photosensitive material in any amount, but the preferred amount is 0.00000000000000000000000 per 1 photosensitive material.
01 to 5 mmol, more preferably 0
．． In the range of 0.01 to 2 mmol. When used in a photosensitive emulsion layer, the amount used is preferably in the range of 0.001 to 1.0 mol, more preferably in the range of 0.002 to 1.0 mol, per 1 mol of photosensitive silver halide. be.

(Example) Next, the present invention will be specifically explained with reference to Examples, but the present invention is not limited thereto.

Example 1 A photosensitive material that develops a monochromatic color was prepared, consisting of two layers, an emulsion layer and a protective layer, on an undercoated cellulose triacetate support. The emulsion layer coating solution was prepared as follows.

Emulsion layer coating solution preparation 0.03 mol of coupler (see Table 1) and 10 g of dibutyl phthalate to 30 ml of ethyl acetate! was added and dissolved, and this solution was emulsified and dispersed in 185 cc of a 10% aqueous gelatin solution containing 8 cc of 10% sodium dodecylbenzenesulfonate. To this was added 300 g of a 10% gelatin solution in which silver iodobromide (24 g in terms of silver) was dispersed to prepare an emulsion layer coating solution.

Silver halide color light-sensitive materials (samples 101 to 111) were prepared using the above coating solution. Each sample was coated within 3 hours after preparing the coating solution (A), and (B) was coated after the coating solution had been stored at 10°C for 3 days.
A type was created for each sample. These are sample 101 (
A) and sample 101(B).

The composition of each sample is shown below. The numerical value represents the amount of coating per square meter (unit: duram). Note that for silver halide, values are shown in terms of silver.

Further, couplers are expressed in moles per square meter.

(Emulsion layer) Silver iodobromide emulsion (silver iodide 2 mol%, average grain size 0.3 μm) Silver 0.8 Gelatin 1.6 Couvlar (first
(See table) 0.001 dibutyl phthalate
0.33 (protective layer) Gelatin 0.9 Polymethyl methacrylate particles (diameter 1.5 μm) 0.41-oxy-3
,5-dichloro-s-1-riazine sodium 0.04 The light-sensitive materials thus prepared (samples 101 to 111) were exposed using a continuous density wedge, and then subjected to the following color development process.

Color development processing Color development 3 minutes 15 seconds Bleaching 6 minutes 30 seconds Fixation 4 minutes 20 seconds Wash with water 5 minutes Stable 1 minute The composition of the treatment liquid used in each step was as follows.

Color developer Diethylenetriaminepentaacetic acid 1.0g 1-Hydroxyethylidene-1,1-diphosphonic acid 2.0g Sodium sulfite 4.0g Potassium carbonate Potassium bromide Potassium iodide Hydroxylamine sulfate 4-(N-ethyl-N-β- Hydroxyethylamino) Add 2-methylaniline sulfate to pH Bleach solution 1.3-diaminopropanetetraacetic acid ferric ammonium salt Ammonia water Ammonium bromide Ammonium nitrate Add water to pH Fixer Ethylenediaminetetraacetic acid 0g 0g 3mg 0g 4 , 5g 1, C1! 10,0 105゜3゜150゜10゜1゜4゜0g ml 0g 0g Oρ Disodium salt 1.0g Sodium sulfite 4.0g Ammonium thiosulfate aqueous solution (70%) 175.0ml Sodium bisulfite 4.6g Add water hand
pH 6.6 at 1.0 Add 2.0 m of stabilized formalin (40%) [J polyoxyethylene-p-monononylphenyl ether (average degree of polymerization: 10) 0.3 g of water
1. Sample (A) that developed cyan color in the Of2 color development process (IOIA~111A
), the gamma value (the slope of the straight line connecting the points of density 0.5 and density 1.0 on the sensitometry curve) and D
max (maximum color density) was measured. The stability of the emulsion was evaluated by the ratio of D max of the corresponding (A) and (B) samples (
(R value shown below) (the closer the R value is to 1.0, the more preferable it is).

Next, in order to evaluate the color increase over time, the colored sample (A) was left at 80°C and 70% for 3 days, and then D m
ax was measured and the following A value was determined (the closer the A value is to 1.0, the better).

tnax These values (gamma value, Dmax, R value, A value) are
Shown in the table. Note that the gamma value and D max are for sample 101.
It is expressed as a relative value when the value at A is set to 1.

Comparative coupler A Described in U.S. Patent No. 4,333,999 Table 1 shows that when the coupler of the present invention is used, both the gamma value and D max are higher than when the comparative coupler A is used, and the coupling activity and color development are It can be seen that the concentration is high. In addition, when the coupler of the present invention is used, it can be seen that there is no problem of a decrease in D max due to aging of the emulsion when refrigerated or an increase in D max due to aging of the coloring sample when heated, unlike when using comparative coupler B. .

Described in JP-A-63-161451 Example 2 On a subbed cellulose triacetate film support,
Samples 201 to 210, which are multilayer color light-sensitive materials, were prepared by applying layers having the compositions shown below.

(Photosensitive layer composition) The number corresponding to each component indicates the coating amount expressed in g/rd unit, and for silver halide, it indicates the coating amount in terms of silver.However, for aggravating dyes, the halogenated amount in the same layer The amount of coating per mole of silver is shown in moles.

1st layer (antihalation N) black colloidal silver silver o, 18 gelatin 1.40 2nd layer (intermediate F 2.5-di-L-pentadecylhydroquinone 0.1SEX-
10,070 E (See table) Eχ-10 B5-1 Gelatin 2, OX 10-3 0.060 0.080 0.10 0.10 0.020 1.04 Silver 0.25 Silver 0.25 6.9X10 bow 1.8X10- ' 3, lX10-'' 0.64 mmol O,020 0,070 0,050 0,070 0,060 0,87 4th layer (second red emulsion layer) Emulsion G Enhanced dye I Enhanced dye ■ Enhanced dye ■ Cyan Coupler (see Table 2) EX-3 EX-10 l-3 Gelatin No. 5N (third red emulsion layer) Emulsion enhancing dye I Sensitizing dye ■ Enhancing dye m x-2 EX-3 EX-, II Silver 1.00 5, lX10-'1.4X10-'2.3X10-' 0.75 mmol O,050 0,015 0,070 o, os.

O,070 1,30 Limit 1.30 5.4XIO-S 1.4X10-' 2.4X10-' 0.097 0.010 0.080 8th Fj (second green emulsion layer) Emulsion C Exacerbating pigment■ Exacerbating pigment■ Exacerbating pigment■ EX-6 EX-7 EX-8 B5-1 B5-3 gelatin 9th layer (3rd green emulsion layer) Emulsion E Exacerbating pigment■ Fa8 dye■ Exacerbating pigment■ EX-1 EX-11 EX-13 B5-1 Silver 0.45 2, lX10-' 7.0X10-' 2.6xlO-' 0.094 0.026 0.018 0.16 B, 0X10-” 0.50 Silver 1.20 3.5xlO-' 8.0X10-' 3.0X10-' 0.025 0.10 0.015 0.25 B5-1 B5-2 gelatin 6th N (middle layer) EX-5 B5-1 gelatin 7th Fj (1st green emulsion layer) Emulsion A Emulsion B Exacerbating pigment■ Sensitizing dye\l Exacerbating pigment■ EX-1 EX-6 EX-7 EX-8 B5-1 B5-3 gelatin 0.22 0.10 1.63 0.040 0.020 0.80 S 艮 0.15 Silver 0415 3, OX 10-5 1.0X10-' 3.8X10-' 0.021 0°26 0.030 0.025 0.10 0.010 0.63 B5-2 gelatin 1st ON (yellow filter layer) yellow colloidal silver EX-5 BS-1 gelatin 117th! (1st Seiyu Emulsion Pi) Emulsion A Emulsion B Emulsion F Exacerbating pigment■ EX-8 EX-9 B5-1 gelatin 12th layer (second blue emulsion N) Emulsion G Exacerbation pigment ~1 EX-9 0,10 1,54 Silver o,os.

O,080 0,030 0,95 Silver o, os.

Silver 0.070 Silver 0.070 3.5X10-' 0.042 0.72 0.28 1.10 Silver 0.45 2, lX10-' 0.15 Eχ-10 HBS-] Gelatin 13th layer (3rd Blue emulsion Fi) Emulsion H Sensitizing dye■ B-2 (diameter 1.7μm) 7,0X10-' 0.050 0°78 Silver 0.77 2.2X10-' 0.20 0.070 0.69! I! 0.20 0.11 0.17 5.0X10-2 1.00 0.40 5.0X10-" 0.10 0.10 S -10,20 Gelatin 1.20 Furthermore,
W-1, W-2,
w-3, B-4, B-5, F-1, F-2, F-3, F
-4, F-5, F-6, F-7, F-8, F-9, F-
10, F-11, F-12, F-13, and iron salt, lead salt, gold salt, platinum salt, iridium salt, and rhodium salt.

X-1 Shi1 Eχ-2 H ■ X-3 H EX-4 EX-5 EX-6 EX-10 EX-12 I CJ50SOze EX-7 EX-8 EX-9 EX-13 (t) CJq Shil U B5-1 Tricresyl phosphinate BS Di-n-butyl phthalate aggravating dye■ Aggravating dye■ Sensitizing dye■ Aggravating dye■ Sensitizing dye■ Sensitizing dye■ Sensitizing dye■ CH,=CH-5o! -CH2-C0NH-(IJhC
H2=CH-3Q, -(:B2-CONH precept H2B-2 2-4 Color photographic materials as above (samples 201-210
) was exposed to red light and then processed as described below.

Processing method engineering color development bleaching bleach fixing Washing with water (1) Washing with water (2) stable drying 38℃ 38℃ 38℃ 35℃ 35℃ 38℃ 55℃ 3 minutes 15 seconds 1 minute 00 seconds 3 minutes 15 seconds 40 seconds 1 minute 00 seconds 40 seconds 1 minute 15 seconds Next, the composition of the treatment liquid will be described.

(Color developer) Diethylenetriaminepentaacetic acid 1-hydroxyethylidene-1,1-diphosphonic acid Sodium sulfite Potassium carbonate (unit: g) 1.0 3, 0 4, 0 30.0 Potassium bromide Potassium iodide Hydroxylamine sulfate 4 -[N-ethyl-N-β-hydroxyethylamino]- Add 2-methylaniline sulfate to pH (bleach solution) Ethylenediaminetetraacetic acid ferric ammonium dihydrate Ethylenediaminetetraacetic acid disodium salt Ammonium bromide Ammonium nitrate Ammonia Water (27%) Add water 1,4 1.5mg 2,4 4.5 1,0℃ 10.05 (unit: g) 120.0 10.0 100.0 10,0 15.0mt 1.0β pH 6.3 (Bleach-fix solution) (Unit g) Ethylenediaminetetraacetic acid ferric ammonium dihydrate 50.0 Ethylenediaminetetraacetic acid disodium salt 5.0 Sodium sulfite 12.0 Ammonium thiosulfate aqueous solution (70%) 240.0ml Ammonia Water (27%") Add 6.0 d of water to 1.0 r2 pH 7.2 (Washing liquid) Tap water was exchanged with H-type strongly acidic cation exchange resin (Amberlite IR-120B manufactured by Rohm and Haas) and OH-type anion exchange. Water was passed through a mixed bed column filled with resin (Amberlite IR-400) to reduce the concentration of calcium and magnesium ions to 3 mg/71 or less, and then sodium incyanurate dichloride 20 mg/42 and sodium sulfate 0. 15g/n was added.The pH of this liquid
is in the range of 6.5 to 7°5.

(Stabilizing solution) (Unit: g) Formalin (37%) 2.0 ml Polyoxyethylene-p-monononylphenyl ether (average degree of polymerization 10) 0.3 Ethylenediaminetetraacetic acid disodium salt 0.05 Add water
1.02pH5.0~8.0 Samples developed by color development (201~210
) was measured. In Table 2, the density of each sample was measured at an exposure dose that gave a density of 1.0 for sample 201.

Table 2 (Note) Comparative coupler A is the same as that used in Example 1.

The results in Table 2 show that when the coupler of the present invention is used, high color density can be obtained even in color light-sensitive materials having a multilayer structure.

Example 3 Multilayer color photographic paper samples 301 to 310 having the layer structure shown below were prepared on a paper support laminated on both sides with polyethylene. The coating solution was prepared as follows.

-Layer coating liquid! Iil yellow coupler (ExY) 19.1 g, color image stabilizer (Cpd-1) 4.4 g and color image stabilizer (C
pd-7) Add and dissolve 27.2 cc of ethyl acetate and 8.2 g of solvent (Solv-3) to 0.7 g, and dissolve this solution in 8 c of 10% sodium dodecylbenzenesulfonate.
The mixture was emulsified and dispersed in 185 cc of a 10% aqueous gelatin solution containing c. On the other hand, silver chlorobromide emulsion C is cubic, with an average grain size of 0.
The coefficient of variation of the particle size distribution of 88- and 0.70-3:7 mixed proboscis (silver molar ratio) is 0.08 and 0.70.
10. Each emulsion contains 0.2 mol% of silver bromide locally on the grain surface], and 2.0 x 10-'' mol of each of the following venereal sensitizing dyes are added per mol of silver for large-sized emulsions. , and 2.5X for small size emulsions, respectively.
A 10-' mole addition followed by sulfur enrichment was prepared.

A first coating liquid was prepared by mixing and melting the emulsified bone 11 and this emulsion to have the composition shown below.

The coating solutions for the second to seventh layers were also prepared in the same manner as the coating solution for the -Nth layer. As a gelatin hardening agent for each layer,! -Oxy-315-dichloro-8-triazine sodium salt was used.

The following spectral enhancing dyes were used in each layer.

Blue-sensitive emulsion layer Green-sensitive emulsion layer (per mole of silver halide, 4.0 x 10-' moles for large size emulsions, 5.6 for small size emulsions)
X 10-' mol) and SOz' 5(hN)I (C,)Is).

(per mole of halogenated EM, 2.0X10-' moles each for large size emulsions and 2.5.X10-' moles each for small size emulsions) )) (per mole of silver halide, 7.0X10-' moles for large emulsions and 1 mole for small emulsions)
．． 0XIO-' moles) red-sensitive emulsion layered i/mole, 5xio-' moles, 7.7X
10-' moles, 2.5 X 10-' moles were added.

The following dyes were added to the emulsion layer to prevent irradiation.

(per mole of silver halide, 0.9X10-' mole for large emulsions and 1 mole for small emulsions)
．． To the red-sensitive emulsion layer, 2.6 x 10-' moles of the following compound was added per mole of the northern limit of halogen.

In addition, 1-(5-methylureidophenyl)-5-mercaptotetrazole was added to each of the blue-sensitive emulsion layer, green-sensitive emulsion layer, and red-sensitive emulsion layer (layer structure) The composition of each layer is shown below. The numbers are coating ffi (g/rr
The silver halide emulsion represented by r) represents the coated amount in terms of silver.

Support polyethylene laminate paper [white Bnl'4 (Too
, ) and a bluish dye (ulmarine)] Layer (IW for blue) Said silver chlorobromide emulsion 0.30 Gelatin 1.86 Yellow coupler (ExY) 0.82 Color image stabilizer (Cpd-1) 0.19 Solvent (Solv-3) 0.3
Five-color image stabilizer (Cpd-7) 0
．． 06 Fifth layer (color mixing prevention N) Gelatin 0.99 Color mixing prevention rule (Cpd-5) 0.08 Solvent (Solv-1) 0.1
674 solvent (Solv-4)
0.08 Fifth layer (green sensitive layer) Silver chlorobromide emulsion (cubic, 1:3 mixture of one with an average grain size of 0.55 grain size and one with an average grain size of 0.39 grains (Ag molar ratio) 0 grain size The coefficient of variation of the distribution is 0.10 and 0.08,
(Each emulsion contained 0.8 mol% of AgBr locally on the grain surface) 0.12 Gelatin
1.24 Magenta coupler (Ex unit) 0.20 Color image stabilizer (Cpd-2
) 0.03 color image stabilizer (Cpd
-3) 0.15 color image stabilizer (C
pd-4) 0.02 color image stabilizer (Cpd-9) 0.02 solvent (
Solv-2) 0.40 Fourth N (ultraviolet absorption layer) Gelatin 1.58 Ultraviolet absorption cutting (υV-1) 0.47 Color mixture prevention agent (Cpd-5) 0.0
5 Solvent (Solv-5) 0
．． 24 Fifth layer (Red Anger N) Silver chlorobromide emulsion (cubic, average grain size 0.58tlI)
1=4 mixture of n and 0.45 groups (Ag
Molar ratio] The coefficient of variation of the particle size distribution is 0.09 and 0.
11. Each emulsion contained 0.6 mol% of AgBr locally on a part of the grain surface) 0.23 gelatin
1.55 cyan coupler (
(See Table 3) 0.3+am+o1 color image stabilizer (Cpd-6) 0.17 color image stabilizer (Cpd-7) color image stabilizer (Cpd-8) solvent (Solv-6) 6th N (ultraviolet absorption N) Gelatin ultraviolet absorber (υv-1) Color mixing prevention agent (Cpd-5) Solvent (Sol Sea 5) Seventh N (protective layer) Gelatin polyvinyl alcohol scum (denaturation degree 17%) Liquid paraffin 0.40 0 .04 0.15 0.53 0.16 0.02 0.08 1.33 Lyle modified copolymer 0.17 0.03 (ExY) Yellow coupler (Cpd-1) 1 with color image stabilizer: ] Mixture (molar ratio) (Ext) 1:l mixture (molar ratio) of Mazenk Couvlar (Cpd-2) Color image stabilizer (Cpd-3) Color image stabilizer (Cpd-4) Color image stabilizer (Cpd-5) Color mixing inhibitor (Cpd-6) Color image stabilizer caoq(t) 2 mixture (weight ratio) of c, nq(t) (Cpd-7) Color image stabilizer 4CII□-CIlh- CON)Ic-11* (n) A 2:1 mixture (volume ratio) of a 1:1 mixture (Solv-1) with an average molecular weight of 60.000 (Solv-2) (Solv-3) (Solv-4) (Cpd) Color Image stabilizer (υv-1) ultraviolet absorption, 4:2:4 mixture (weight ratio) of agent 1 (t) (Solv-5)?Container C00CsH+t (CHz)s C00Call+t (Solv-6)?Container First , each sample (301 to 310) was exposed to red light. After the exposure, the sample was processed continuously using a paper processing machine until twice the capacity of the color developing tank was replenished in the next processing step. (running test) was conducted.

Processing process: Color development: 35°C, 45 seconds, 161m, 1171L Bleach: 30
~35°C 45 seconds 215 ml 17 Poor rinse■
30~35"C20 seconds -102 rinse■ 30~3
5°C 20 seconds -102 rinse■ 30~35°C20
seconds 350m1 101 drying 70~80°C
The 60-second, 11-replenishment type was a 3-tank, 7-way system with 1 n of oxidizing material (per rinsing ■→■).The composition of each treatment solution was as follows.

Yo J1 Mupi 1 dish light hill water 800 tn
l 800 mQ ethylenediamine-N,N.

N,N-tetramethylenephosboxylic acid 1.5 g 2.0 g
Triethanolamine Sodium chloride Potassium carbonate N-ethyl-N-(β-methanesulfonamidoethyl)-3-methyl-4 Aminoaniline sulfate N,N-bis(carboxymethyl)hydrazine Optical brightener (WHITEX 4B 8. 0 g 1.4 g 5.0 g 5.5 g Add water 1000zz!pl+
(25”C) 10.051 Soystick 1 blood (tank fluid and replenishment fluid are the same) Ammonium hydrothiosulfate (70%) Sodium sulfite Iron ethylenediaminetetraacetate (I [I) Disodium ammonium ethylenediaminetetraacetate 12.0 g 000 mN 10.45 400 m2 00 mN 7 g 5 g 5 g Ammonium bromide 40 g Add water 1000 mlp)I
(25°0 6.0 non-emulsion (tank fluid and refill fluid are the same) Ion exchange water (calcium and magnesium are each 3 points)
P11 or below) Samples developed by color development (301-310
) was measured. Table 3 shows the density of each sample at the exposure dose that gave a reflection density of 1.0 in sample 301.

Table 3 (Note) Comparison coupler A Same as shown in Example 1.

The results in Table 3 show that when the coupler of the present invention is used, high color density can be obtained even in reflective color light-sensitive materials having a multilayer structure.

(Effects of the Invention) From the above results, the silver halide color photographic light-sensitive material of the present invention has a high coupling reactivity of cyan coupler and 1
An excellent effect is achieved in that the color density of the image is high. Further, the silver halide color photographic light-sensitive material of the present invention exhibits excellent effects in that the cyan coupler dispersion undergoes little deterioration due to storage and there is no problem of color increase in colored images.

(Procedures from Zheng Shue) July 29, 1991

Claims (1)

[Scope of Claims] A silver halide color photographic light-sensitive material having at least one silver halide emulsion layer on a support, at least one cyan compound represented by the following general formula (I-a) or (I-b). A silver halide color photographic material characterized by containing a dye-forming coupler. General formula (I-a) ▲There are mathematical formulas, chemical formulas, tables, etc.▼ ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (In the formula, R^1 is an alkyl group, an alkenyl group, a cycloalkyl group, an aryl group, a heterocycle group, alkoxy group, aryloxy group or amino group, and R^2 is R^
1 or a hydrogen atom, an acyl group, or an alkoxycarbonyl group, Q is a monocyclic ring containing 4 to 7 atoms in the ring together with the carbon atom to which R^1SO_1- is bonded ~
X is the nonmetallic atom necessary to form an alicyclic or heterocyclic ring consisting of four rings, and
Along with O_2, a monocyclic ring each containing 4 to 7 atoms in the ring ~
Ar represents a nonmetallic atom necessary to form an alicyclic or heterocyclic ring consisting of four rings, Ar represents an aryl group or a heterocyclic group, and Z represents a hydrogen atom or an aromatic primary amine developer. Represents a group that can be separated by a coupling reaction with an oxidant. )