EP0488248A1
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Cyan image forming method and silver halide color photographic material containing cyan coupler
Assignee: Fujifilm Holdings Corp
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Filing: 1991-11-27
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Granted: —
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Expires: 2011-11-27
Abstract
Abstract A silver halide color photographic material comprising a support having thereon at least one light-sensitive silver halide emulsion layer containing at least one lH-pyrrolo[2,l-c][l,2,4]triazole cyan coupler represented by the following general formula (I) or (II): wherein R₁, R₂ and R₃ each represents a hydrogen atom or a substituent, provided that at least one of R₁ and R₂ is an electron withdrawing group which has a Hammett's substituent constant σp value of 0.15 or more; R₁ and R₂ may be bonded to form a ring; and X represents a hydrogen atom or a substituent capable of being released upon coupling with an oxidation product of an aromatic primary amine color developing agent; said coupler may form a bis-compound or or a polymer at R₁, R₂, R₃ or X; and a cyan image forming method comprising imagewise exposing a silver halide color photographic material comprising a support having thereon at least one light-sensitive silver halide emulsion layer and subjecting the exposed photographic material to color development with an aromatic primary amine color dveloping agent at the presence of the above-described lH-pyrrolo[2,l-c][l,2,4]triazole cyan coupler.
Inventors
- 👤 Makoto C/O Fuji Photo Film Co. Ltd. Suzuki
- 👤 Tadahisa C/O Fuji Photo Film Co. Ltd. Sato
- 👤 Kozo C/O Fuji Photo Film Co. Ltd. Sato
- 👤 Yoshio C/O Fuji Photo Film Co. Ltd. Ishii
Bibliographic Details
Application Number
—
Jurisdiction
EP
Data Source
google_patents
Last Synchronized
2026-11-04 08:07
CPC Classifications
G; G03; G03C; G03C7/00; G03C7/30; G03C7/305; G03C7/30511; G03C7/30517; G03C7/30529; G03C7/32; G03C7/36; G03C7/38; G03C7/381; G03C7/382; G03C7/3825; G03C7/383
Claims Analysis
Total Claims: 38
Claim 1
Independent Claim
126 words
A silver halide color photographic material comprising a support having thereon at least one light-sensitive silver halide emulsion layer containing at least one lH-pyrrolo[2,l-c][l,2,4]triazole cyan coupler represented by the following general formula (I) or (II): wherein R₁, R₂ and R₃ each represents a hydrogen atom or a substituent, provided that at least one of R₁ and R₂ is an electron withdrawing group which has a Hammett's substituent constant σp value of 0.15 or more; R₁ and R₂ may be bonded to form a ring; and X represents a hydrogen atom or a substituent capable of being released upon coupling with an oxidation product of an aromatic primary amine color developing agent; said coupler may form a bis-compound or a polymer at R₁, R₂, R₃ or X.
Claim 2
Dependent Claim
24 words
A silver halide color photographic material as claimed in Claim 1, wherein lH-pyrrolo[2,l-c][l,2,4]-triazole cyan coupler is contained in a red-sensitive silver halide emulsion layer.
Claim 3
Dependent Claim
22 words
A silver halide color photographic material as claimed in Claim 1, wherein a Hammett's substituent constant σp value is 0.20 or more.
Claim 4
Dependent Claim
22 words
A silver halide color photographic material as claimed in Claim 1, wherein a Hammett's substituent constant σp value is 0.30 or more.
Claim 5
Dependent Claim
22 words
A silver halide color photographic material as claimed in Claim 1, wherein a Hammett's substituent constant σp value is 0.60 or more.
Claim 6
Dependent Claim
22 words
A silver halide color photographic material as claimed in Claim 1, wherein a Hammett's substituent constant σp value is 1.0 or less.
Claim 7
Dependent Claim
32 words
A silver halide color photographic material as claimed in Claim 1, wherein at least R₁ is an electron withdrawing substituent which has a Hammett's substituent constant σp value of 0.15 or more.
Claim 8
Dependent Claim
47 words
A silver halide color photographic material as claimed in Claim 1, wherein at least one of R₁ and R₂ is an electron withdrawing substituent having a Hammett's substituent constant σp value of 0.15 or more and the other of R₁ and R₂ is an electron withdrawing substituent.
Claim 9
Dependent Claim
32 words
A silver halide color photographic material as claimed in Claim 1, wherein R₁ and R₂ each represents an electron withdrawing substituent having a Hammett's substituent constant σp value of 0.15 or more.
Claim 10
Dependent Claim
32 words
A silver halide color photographic material as claimed in Claim 1, wherein R₁ and R₂ each represents an electron withdrawing substituent having a Hammett's substituent constant σp value of 0.20 or more.
Claim 11
Dependent Claim
35 words
A silver halide color photographic material as claimed in Claim 5, wherein the sum of the Hammett's substituent constant σp values of the electron withdrawing substituents represented by R₁ and R₂ is 0.60 or more.
Claim 12
Dependent Claim
35 words
A silver halide color photographic material as claimed in Claim 1, wherein the sum of the Hammett's substituent constant σp values of the electron withdrawing substituents represented by R₁ and R₂ is 1.8 or less.
Claim 13
Dependent Claim
228 words
A silver halide color photographic material as claimed in Claim 1, wherein the substituent represented by R₁, R₂ or R₃ is selected from the group consisting of a halogen atom, an alkyl group, an aryl group, a heterocyclic group, a cyano group, a hydroxy group, a nitro group, a carboxy group, a sulfo group, an amino group, an alkoxy group, an aryloxy group, an acylamino group, an alkylamino group, an anilino group, a ureido group, a sulfamoylamino group, an alkylthio group, an arylthio group, an alkoxycarbonylamino group, an alkyl- or aryl-sulfonamido group, a carbamoyl group, a sulfamoyl group, an alkyl- or aryl-sulfonyl group, an alkyl- or aryl-sulfonyloxy group, an alkoxycarbonyl group, a heterocyclic oxy group, an alkyl- or aryl-azo group, an alkyl- or aryl-oxysulfonyl group, an acyloxy group, a carbamoyloxy group, a silyloxy group, an aryloxycarbonylamino group, an imido group, a seleno-cyanate group, a heterocyclic thio group, an alkyl- or aryl-sulfinyl group, a phosphinyl group, a phosphonyl group, a phosphono group, an aryloxycarbonyl group, an acyl group, an acylthio group, an azolyl group, an isocyanate, a thiocyanate group and an alkyl- or aryl-thiocarbonyl group; these groups may be further substituted with at least one of these substituents; R₁ and R₂ may be bonded to form a ring, and at least one of R₁ and R₂ is selected from these groups having a σp value of 0.15 or more.
Claim 14
Dependent Claim
151 words
A silver halide color photographic material as claimed in Claim 13, wherein the electron withdrawing substituent having a Hammett's substituent constant σp value of 0.15 or more is an acyl group, an acyloxy group, a carbamoyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, a cyano group, a nitro group, a dialkylphosphono group, a diarylphosphono group, a diarylphosphinyl group, an alkylsulfinyl group, an arylsulfinyl group, an alkylsulfonyl group, an arylsulfonyl group, an alkylthio group, an arylthio group, an alkyl-or aryl-oxysulfonyl group, an acylthio group, a sulfamoyl group, an isocyanate group, a thiocyanate group, an alkyl- or aryl-thiocarbonyl group, a halogenated alkyl group, a halogenated alkoxy group, a halogenated aryloxy group, a halogenated alkylamino group, a halogenated alkylthio group, a substituted aryl group, a heterocyclic group, a chlorine atom, a bromine atom, an alkyl- or aryl-azo group or a selenocyanate group; these substituents may further have at least one substituent defined for R₃.
Claim 15
Dependent Claim
158 words
A silver halide color photographic material as claimed in Claim 13, wherein the electron withdrawing substituent having a Hammett's substituent constant σp value of 0.20 or more is an acyl group, an acyloxy group, a carbamoyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, a cyano group, a nitro group, a dialkylphosphono group, a diarylphosphono group, a diarylphosphinyl group, an alkylsulfinyl group, an arylsulfinyl group, an alkylsulfonyl group, an arylsulfonyl group, an alkyloxysulfonyl group, an aryloxysulfonyl group, an acylthio group, a sulfamoyl group, a thiocyanate group, an alkyl- or aryl-thiocarbonyl group, a halogenated alkyl group, a halogenated alkoxy group, a halogenated aryloxy group, a halogenated alkylamino group, a halogenated alkylthio group, an aryl group substituted with other electron withdrawing group having the σp value of not less than 0.20, a heterocyclic group, a chlorine atom, a bromine atom, an alkyl- or aryl-azo group or a selenocyanate group; these substituents may further have at least one substituent defined for R₃.
Claim 16
Dependent Claim
120 words
A silver halide color photographic material as claimed in Claim 13, wherein the electron withdrawing substituent having a Hammett's substituent constant σp value of 0.30 or more is an acyl group, an acyloxy group, a carbamoyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, a cyano group, a nitro group, an alkylsulfinyl group, an arylsulfinyl group, an alkylsulfonyl group, an arylsulfonyl group, a sulfamoyl group, a halogenated alkyl group, a halogenated alkoxy group, a halogenated aryloxy group, a halogenated alkylthio group, an aryl group substituted with two or more other electron withdrawing substituents each having a Hammett's substituent constant σp value of 0.15 or more or a heterocyclic group; these substituents may further have at least one substituent defined for R₃.
Claim 17
Dependent Claim
51 words
A silver halide color photographic material as claimed in Claim 13, wherein the electron withdrawing substituent having a Hammett's substituent constant σp value of 0.60 or more is a cyano group, a nitro group or an alkylsulfonyl group which may be further substituted with at least one substituent defined for R₃.
Claim 18
Dependent Claim
45 words
A silver halide color photographic material as claimed in Claim 13, wherein the heterocyclic moiety in the substituents is a 5- to 7-membered heterocyclic moiety containing at least one of N, O and S atoms and may be condensed with a phenyl or naphthyl group.
Claim 19
Dependent Claim
34 words
A silver halide color photographic material as claimed in Claim 1, wherein the lH-pyrrolo[2,l-c][l,2,4]-triazole cyan coupler is contained in an amount of 1 x 10⁻³ to 1 mol per mol of light-sensitive silver halide.
Claim 20
Dependent Claim
36 words
A silver halide color photographic material as claimed in Claim 1, wherein the lH-pyrrolo[2,l-c][l,2,4]-triazole cyan coupler is capable of forming a cyan dye having a maximum wavelength in the range of from 600 to 700 nm.
Claim 21
Dependent Claim
152 words
A cyan image forming method comprising imagewise exposing a silver halide color photographic material comprising a support having thereon at least one light-sensitive silver halide emulsion layer and subjecting the exposed photographic material to color development with an aromatic primary amine color dveloping agent at the presence of an lH-pyrrolo[2,l-c][l,2,4]triazole cyan coupler represented by the general formula (I) or (II): wherein R₁, R₂ and R₃ each represents a hydrogen atom or a substituent, provided that at least one of R₁ and R₂ is an electron withdrawing group which has a Hammett's substituent constant σp value of 0.15 or more; R₁ and R₂ may be bonded to form a ring; and X represents a hydrogen atom or a substituent capable of being released upon coupling with an oxidation product of an aromatic primary amine color developing agent; said coupler may form a bis-compound or or a polymer at R₁, R₂, R₃ or X.
Claim 22
Dependent Claim
30 words
A cyan image forming method as claimed in Claim 21, wherein the lH-pyrrolo[2,l-c][l,2,4]triazole cyan coupler is incorporated in a color developing solution containing the aromatic primary amine color developing agent.
Claim 23
Dependent Claim
38 words
A cyan image forming method as claimed in Claim 22, wherein the lH-pyrrolo[2,l-c][l,2,4]triazole cyan coupler is incorporated in a color developing solution in an amount of from 0.0005 to 0.05 mol per liter of the color developing solution.
Claim 24
Dependent Claim
23 words
A cyan image forming method as claimed in Claim 21, wherein lH-pyrrolo[2,l-c][l,2,4]triazole cyan coupler is contained in the light-sensitive silver halide emulsion layer.
Claim 25
Dependent Claim
21 words
A cyan image forming method as claimed in Claim 21, wherein a Hammett's substituent constant σp value is 0.20 or more.
Claim 26
Dependent Claim
21 words
A cyan image forming method as claimed in Claim 21, wherein a Hammett's substituent constant σp value is 0.30 or more.
Claim 27
Dependent Claim
21 words
A cyan image forming method as claimed in Claim 21, wherein a Hammett's substituent constant σp value is 0.60 or more.
Claim 28
Dependent Claim
31 words
A cyan image forming method as claimed in Claim 21, wherein at least R₁ is an electron withdrawing substituent which has a Hammett's substituent constant σp value of 0.15 or more.
Claim 29
Dependent Claim
46 words
A cyan image forming method as claimed in Claim 21, wherein at least one of R₁ and R₂ is an electron withdrawing substituent having a Hammett's substituent constant σp value of 0.15 or more and the other of R₁ and R₂ is an electron withdrawing substituent.
Claim 30
Dependent Claim
31 words
A cyan image forming method as claimed in Claim 21, wherein R₁ and R₂ each represents an electron withdrawing substituent having a Hammett's substituent constant σp value of 0.15 or more.
Claim 31
Dependent Claim
31 words
A cyan image forming method as claimed in Claim 21, wherein R₁ and R₂ each represents an electron withdrawing substituent having a Hammett's substituent constant σp value of 0.20 or more.
Claim 32
Dependent Claim
34 words
A cyan image forming method as claimed in Claim 27, wherein the sum of the Hammett's substituent constant σp values of the electron withdrawing substituents represented by R₁ and R₂ is 0.60 or more.
Claim 33
Dependent Claim
226 words
A cyan image forming method as claimed in Claim 21, wherein the substituent represented by R₁, R₂ or R₃ is selected from the group consisting of a halogen atom, an alkyl group, an aryl group, a heterocyclic group, a cyano group, a hydroxy group, a nitro group, a carboxy group, a sulfo group, an amino group, an alkoxy group, an aryloxy group, an acylamino group, an alkylamino group, an anilino group, a ureido group, a sulfamoylamino group, an alkylthio group, an arylthio group, an alkoxycarbonylamino group, an alkyl- or arylsulfonamido group, a carbamoyl group, a sulfamoyl group, an alkyl- or aryl-sulfonyl group, an alkyl- or arylsulfonyloxy group, an alkoxycarbonyl group, a heterocyclic oxy group, an alkyl- or aryl-azo group, an alkyl-or aryl-oxysulfonyl group, an acyloxy group, a carbamoyloxy group, a silyloxy group, an aryloxycarbonylamino group, an imido group, a selenocyanate group, a heterocyclic thio group, an alkyl- or arylsulfinyl group, a phosphinyl group, a phosphonyl group, a phosphono group, an aryloxycarbonyl group, an acyl group, an acylthio group, an azolyl group, an isocyanate, a thiocyanate group and an alkyl- or arylthiocarbonyl group; these groups may be further substituted with at least one of these substituents; R₁ and R₂ may be bonded to form a ring; and at least one of R₁ and R₂ is selected from these groups having a σp value of 0.15 or more.
Claim 34
Dependent Claim
151 words
A cyan image forming method as claimed in Claim 33, wherein the electron withdrawing substituent having a Hammett's substituent constant σp value of 0.15 or more is an acyl group, an acyloxy group, a carbamoyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, a cyano group, a nitro group, a dialkylphosphono group, a diarylphosphono group, a diarylphosphinyl group, an alkylsulfinyl group, an arylsulfinyl group, an alkylsulfonyl group, an arylsulfonyl group, an alkylthio group, an arylthio group, an alkyl- or aryl-oxysulfonyl group, an acylthio group, a sulfamoyl group, an iso-cyanate group, a thiocyanate group, an alkyl- or arylthiocarbonyl group, a halogenated alkyl group, a halogenated alkoxy group, a halogenated aryloxy group, a halogenated alkylamino group, a halogenated alkylthio group, a substituted aryl group, a heterocyclic group, a chlorine atom, a bromine atom, an alkyl- or aryl-azo group or a selenocyanate group; these substituents may further have at least one substituent defined for R₃.
Claim 35
Dependent Claim
157 words
A cyan image forming method as claimed in Claim 33, wherein the electron withdrawing substituent having a Hammett's substituent constant σp value of 0.20 or more is an acyl group, an acyloxy group, a carbamoyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, a cyano group, a nitro group, a dialkylphosphono group, a diarylphosphono group, a diarylphosphinyl group, an alkylsulfinyl group, an arylsulfinyl group, an alkylsulfonyl group, an arylsulfonyl group, an alkyloxysulfonyl group, an aryloxysulfonyl group, an acylthio group, a sulfamoyl group, a thiocyanate group, an alky-or aryl-thiocarbonyl group, a halogenated alkyl group, a halogenated alkoxy group, a halogenated aryloxy group, a halogenated alkylamino group, a halogenated alkylthio group, an aryl group substituted with other electron withdrawing group having the σp value of not less than 0.20, and a heterocyclic group, a chlorine atom, a bromine atom, an alkyl- or aryl-azo group or a selenocyanate group; these substituents may further have at least one substituent defined for R₃.
Claim 36
Dependent Claim
119 words
A cyan image forming method as claimed in Claim 33, wherein the electron withdrawing substituent having a Hammett's substituent constant σp value of 0.30 or more is an acyl group, an acyloxy group, a carbamoyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, a cyano group, a nitro group, an alkylsulfinyl group, an arylsulfinyl group, an alkylsulfonyl group, an arylsulfonyl group, a sulfamoyl group, a halogenated alkyl group, a halogenated alkoxy group, a halogenated aryloxy group, a halogenated alkylthio group, an aryl group substituted with two or more other electron withdrawing substituents each having a Hammett's substituent constant σp value of 0.15 or more or a heterocyclic group; these substituents may further have at least one substituent defined for R₃.
Claim 37
Dependent Claim
62 words
A cyan image forming method as claimed in Claim 33, wherein the electron withdrawing substituent having a Hammett's substituent constant σp value of 0.60 or more are having a Hammett's substituent constant σp value of 0.60 or more are a cyano group, a nitro group and an alkylsulfonyl group which may be further substituted with at least one substituent defined for R₃.
Claim 38
Dependent Claim
35 words
A cyan image forming method as claimed in Claim 21, wherein the lH-pyrrolo[2,l-c][l,2,4]-triazole cyan coupler is capable of forming a cyan dye having a maximum wavelength in the range of from 600 to 700 nm.
References Cited (Backward Citations)
EP0119741A2
Cited
EP0342637A2
Cited
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