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US4310619A Expired / Lapsed US ⏱️ 0.0 years remaining

Color photographic material and process incorporating a novel magenta coupler

Assignee: Fujifilm Holdings Corp
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Filing: 1980-03-03
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Granted: 1982-01-12
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Expires: 2000-03-03
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Abstract

Abstract A color photographic material and a method of forming a color photographic image which utilizes a 5-pyrazolone magenta coupler shown by the following general formula (I): ##STR1## wherein R represents an acylamino group, an anilino group or a ureido group; R 1 , R 2 and R 3 , which may be the same or different, each represents a hydrogen atom, a halogen atom, an alkyl group, an alkenyl group, a cycloalkyl group, an aralkyl group, an alkoxy group, an aryloxy group, a carboxy group, an aryl group or a heterocyclic group (which groups may be substituted) and R.sub. and R 2 may combine to form a 2-indazolyl group, provided that R 1 , R 2 and R 3 are not hydrogen atoms at the same time; and Ar represents a phenyl group which may be substituted with one or more halogen atoms, alkyl groups, alkoxy groups or cyano groups. These 5-pyrazolone magenta couplers are two-equivalent magenta couplers and particularly suitable for providing silver halide color photographic light-sensitive materials having high sensitivity.

Inventors

  • 👤 Seiji Ichijima
  • 👤 Yoshiharu Yabuki
  • 👤 Toshiyuki Watanabe
  • 👤 Nobuo Furutachi

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-31 20:44
CPC Classifications
G; G03; G03C; G03C7/00; G03C7/30; G03C7/32; G03C7/36; G03C7/38; G03C7/384

Claims Analysis

Total Claims: 27
Claim 1
Independent Claim 145 words
A color photographic light-sensitive material comprising a support having thereon at least one emulsion layer containing a 5-pyrazolone magenta coupler represented by the formula (I): ##STR8## wherein R represents an acylamino group, an anilino group or a ureido group; R 1 , R 2 and R 3 , which may be the same or different, each represents a hydrogen atom, a halogen atom, an alkyl group, an alkenyl group, a cycloalkyl group, an aralkyl group, an alkoxy group, an aryloxy group, a carboxy group, an aryl group or a heterocyclic group and R 1 and R 2 may combine to form a 2-indazolyl group, provided that R 1 , R 2 and R 3 are not hydrogen atoms at the same time; and Ar represents a phenyl group which may be substituted with one or more halogen atoms, alkyl groups, alkoxy groups or cyano groups.
Claim 2
Dependent Claim 145 words
A color photographic light-sensitive material comprising a support having thereon at least one emulsion layer containing a 5-pyrazolone magenta coupler represented by the formula (I): ##STR8## wherein R represents an acylamino group, an anilino group or a ureido group; R 1 , R 2 and R 3 , which may be the same or different, each represents a hydrogen atom, a halogen atom, an alkyl group, an alkenyl group, a cycloalkyl group, an aralkyl group, an alkoxy group, an aryloxy group, a carboxy group, an aryl group or a heterocyclic group and R 1 and R 2 may combine to form a 2-indazolyl group, provided that R 1 , R 2 and R 3 are not hydrogen atoms at the same time; and Ar represents a phenyl group which may be substituted with one or more halogen atoms, alkyl groups, alkoxy groups or cyano groups.
Claim 3
Dependent Claim 39 words
The light-sensitive material of claim 1, wherein R represents an acylamino group selected from the group consisting of an acetamido group, a benzamido group, a 3-[α-(2,4-di-tert-amylphenoxy)butyramido]benzamido group, a 3-[α(2,4-di-tert-amylphenoxy)acetamido]benzamido a 3-[α-(3-pentadecylphenoxy)butyramido]benzamido group, an α-(2,4-di-tert-amylphenoxy)butyramido group, and an α-(3-pentadecylphenoxy)butyramido group.
Claim 4
Dependent Claim 46 words
The light-sensitive material of claim 1, wherein R represents an anilino group selected from the group consisting of an anilino group, a 2-chloroanilino group, a 2,4-dichloroanilino group, a 2-chloro-5-tetradecanamidoanilino group, a 2-chloro-5-(2-octadecenylsuccinimido)anilino group, a 2-chloro-5-[α-(3-tert-butyl-4-hydroxy)tetradecanamido]anilino group, a 2-chloro-5-tetradecyloxycarbonylanilino group, a 2-chloro-5-(N-tetradecylsulfamoyl)anilino group, and a 2,4-dichloro-5-tetradecyloxyanilino group.
Claim 5
Dependent Claim 34 words
The light-sensitive material of claim 1, wherein R represents a ureido group selected from the group consisting of a 3-[(2,4-di-tert-amylphenoxy)acetamido]phenylurido group, a phenylureido group, a methylureido group, an octadecylureido group, and a 3-tetradecanamidophenylureido group.
Claim 6
Dependent Claim 97 words
The light-sensitive material of claim 1, wherein the 4-position of said 5-pyrazolone ring is substituted by a moiety of the formula (II): ##STR9## wherein R 1 , R 2 and R 3 in the formula (II), which may be the same or different, each represents a hydrogen atom, a halogen atom, an alkyl group, an alkenyl group, a cycloalkyl group, an aralkyl group, an alkoxy group, an aryloxy group, a carboxy group, an aryl group or a heterocyclic group provided that R 1 , R 2 and R 3 are not hydrogen atoms at the same time.
Claim 7
Dependent Claim 77 words
The light-sensitive material of claim 1, wherein the 4-position of said 5-pyrazolone ring is substituted by a moiety represented by the formula (III): ##STR10## wherein R 5 , R 6 , R 7 and R 8 which may be the same or different, each represents a hydrogen atom, an alkyl group, an alkenyl group, a cycloalkyl group or an aralkyl group and R 3 in the formula (III) is as defined for R 3 in claim 1.
Claim 8
Dependent Claim 19 words
The light-sensitive material of claim 1, wherein said 5-pyrazolone magenta coupler is present in a silver halide emulsion layer.
Claim 9
Dependent Claim 15 words
The light-sensitive material of claim 7, wherein said emulsion layer is a green-sensitive emulsion layer.
Claim 10
Dependent Claim 50 words
The light-sensitive material of claim 8 comprising a support having thereon at least one blue-sensitive silver halide emulsion layer containing a yellow color forming coupler, said green-sensitive silver halide emulsion layer containing said magenta color forming coupler and a red-sensitive silver halide emulsion layer containing a cyan color forming coupler.
Claim 11
Dependent Claim 13 words
The light-sensitive material of claim 9, wherein said color forming couplers are non-diffusible.
Claim 12
Dependent Claim 42 words
The light-sensitive material of claim 5, wherein said moiety represented by the formula (II) is selected from the group consisting of 3,5-dimethylpyrazolyl, 4-methylpyrazolyl, 4-chloropyrazolyl, 3-methyl-5-chloropyrazolyl, 4-t-butylpyrazolyl, 4-benzylpyrazolyl, 4-methoxypyrazolyl, 4-octyloxypyrazolyl, 4-carboxypyrazolyl, 4-phenylpyrazolyl, 4-octylpyrazolyl, 4-(2-thiazolyl)pyrazolyl, 4-carboxymethylpyrazolyl, 4-ethyloxycarbonylmethylpyrazolyl, 3,5-dichloropyrazolyl, 4-bromopyrazolyl, 4-ethylpyrazolyl, 3-chloropyrazolyl, 4-n-butylpyrazolyl and 4-n-hexadecylpyrazolyl.
Claim 13
Dependent Claim 18 words
The light-sensitive material of claim 1, wherein said magenta coupler is a complex coupler of the formula (I).
Claim 14
Dependent Claim 16 words
The light-sensitive material of claim 1, wherein Ar or R contains 8 or more carbon atoms.
Claim 15
Dependent Claim 15 words
The light-sensitive material of claim 1, wherein Ar or R contains a water solubilitizing group.
Claim 16
Dependent Claim 36 words
The light-sensitive material of claim 7, wherein said silver halide emulsion layer containing said magenta coupler of the formula (I) contains silver halide in an amount of about 1×10 -3 to 3×10 -1 mol/m 2 .
Claim 17
Dependent Claim 30 words
The light-sensitive material of claim 15, wherein said coupler of the formula (I) is present in an amount of about 2×10 -1 to 5×10 -1 mol per mol of silver.
Claim 18
Dependent Claim 158 words
A process for forming a color photographic image which comprises processing a silver halide color photographic light-sensitive material in the presence of a 5-pyrazolone magenta coupler represented by the following formula (I): ##STR11## wherein R represents an acylamino group, an anilino group or a ureido group; R 1 , R 2 and R 3 , which may be the same or different, each represents a hydrogen atom, a halogen atom, an alkyl group, an alkenyl group, a cycloalkyl group, an aralkyl group, an alkoxy group, an aryloxy group, a carboxy group, an aryl group or a heterocyclic group wherein said group may be substituted and R 1 and R 2 may combine to form a 2-imidazolyl group, provided that R 1 , R 2 and R 3 are not hydrogen atoms at the same time; and Ar represents a phenyl group which may be substituted with one or more halogen atoms, alkyl groups, alkoxy groups or cyano groups.
Claim 19
Dependent Claim 158 words
A process for forming a color photographic image which comprises processing a silver halide color photographic light-sensitive material in the presence of a 5-pyrazolone magenta coupler represented by the following formula (I): ##STR11## wherein R represents an acylamino group, an anilino group or a ureido group; R 1 , R 2 and R 3 , which may be the same or different, each represents a hydrogen atom, a halogen atom, an alkyl group, an alkenyl group, a cycloalkyl group, an aralkyl group, an alkoxy group, an aryloxy group, a carboxy group, an aryl group or a heterocyclic group wherein said group may be substituted and R 1 and R 2 may combine to form a 2-imidazolyl group, provided that R 1 , R 2 and R 3 are not hydrogen atoms at the same time; and Ar represents a phenyl group which may be substituted with one or more halogen atoms, alkyl groups, alkoxy groups or cyano groups.
Claim 20
Dependent Claim 97 words
The process of claim 17, wherein said group connected to the 4-position of the pyrazolone ring is represented by the formula (II): ##STR12## wherein R 1 , R 2 and R 3 in the formula (II), which may be the same or different, each represents a hydrogen atom, a halogen atom, an alkyl group, an alkenyl group, a cycloalkyl group, an aralkyl group, an alkoxy group, an aryloxy group, a carboxy group, an aryl group or a heterocyclic group, provided that R 1 , R 2 and R 3 are not hydrogen atoms at the same group.
Claim 21
Dependent Claim 77 words
The process of claim 17, wherein said group connected to the 4-position of the pyrazolone ring is represented by the formula (III): ##STR13## wherein R 5 , R 6 , R 7 and R 8 , which may be the same or different, each represents a hydrogen atom, an alkyl group, an alkenyl group, a cycloalkyl group or an aralkyl group and R 3 in the formula (III) is as defined for R 3 in claim 17.
Claim 22
Dependent Claim 19 words
The process of claim 17, wherein said 5-pyrazolone magenta coupler is present in a silver halide color photographic material.
Claim 23
Dependent Claim 16 words
The process of claim 17, wherein said 5-pyrazolone magenta coupler is present in a color developer.
Claim 24
Dependent Claim 15 words
The process of claim 17 which comprises blixing said color photographic material after color development.
Claim 25
Dependent Claim 13 words
The process of claim 17, wherein said process is a diffusion transfer process.
Claim 26
Dependent Claim 178 words
The light-sensitive material of claim 1, wherein R 1 to R 3 may bear one or more substituents selected from the group consisting of a halogen atom, a nitro group, a cyano group, a thiocyano group, an aryl group, an alkoxy group, an aryloxy group, a carboxy group, an alkylcarbonyl group, an arylcarbonyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, a sulfo group, an acyloxy group, a sulfamoyl group, a carbamoyl group, an acylamino group, a diacylamino group, a ureido group, a thioureido group, a urethane group, a thiourethane group, a sulfonamide group, a heterocyclic group, an arylsulfonyloxy group, an alkylsulfonyloxy group, an arylsulfonyl group, an alkylsulfonyl group, an arylthio group, an alkylthio group, an alkylsulfinyl group, an arylsulfinyl group, an alkylamino group, a dialkylamino group, an anilino group, an N-alkylanilino group, an N-arylanilino group, an N-acylanilino group, a hydroxy group, a mercapto group and when R 1 to R 3 represent an aryl group or a heterocyclic group, they may be further substituted by an alkyl group, an alkenyl group, a cycloalkyl group, or an aralkyl group.
Claim 27
Dependent Claim 179 words
The process of claim 17, wherein R 1 to R 3 may be substituted by one or more substituents selected from the group consisting of a halogen atom, a nitro group, a cyano group, a thiocyano group, an aryl group, an alkoxy group, an aryloxy group, a carboxy group, an alkylcarbonyl group, an arylcarbonyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, a sulfo group, an acyloxy group, a sulfamoyl group, a carbamoyl group, an acylamino group, a diacylamino group, a ureido group, a thioureido group, a urethane group, a thiourethane group, a sulfonamido group, a heterocyclic group, an arylsulfonyloxy group, an alkylsulfonyloxy group, an arylsulfonyl group, an akylsulfonyl group, an arylthio group, an alkylthio group, an alkylsulfinyl group, an arylsulfinyl group, an alkylamino group, a dialkylamino group, an anilino group, an N-alkylanilino group, an N-arylanilino group, an N-acylanilino group, a hydroxy group, a mercapto group and when R 1 to R 3 represent an aryl group or a heterocyclic group, they may be further substituted by an alkyl group, an alkenyl group, a cycloalkyl group or an aralkyl group.

References Cited (Backward Citations)

US3990899A Cited
US4049458A Cited
DE2536191A1 Cited
US4076533A Cited
US4133686A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1985-01-11 1985-07-13 1986-01-12 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1989-01-11 1989-07-13 1990-01-12 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1993-01-11 1993-07-13 1994-01-12 $7700.00 Window Closed / Lapsed

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