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US4072525A Expired / Lapsed US ⏱️ 0.0 years remaining

Silver halide photographic material containing two-equivalent color coupler

Assignee: Fujifilm Holdings Corp
•
Filing: 1976-08-04
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Granted: 1978-02-07
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Expires: 1996-08-04
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Abstract

Abstract A photographic color coupler in which a hydrogen atom at the coupling position capable of coupling with an oxidation product of an aromatic primary amine developing agent is substituted with a group represented by the following general formula: ##STR1## wherein R and R', which may be the same or different, each represents an alkyl group, an alkenyl group, an aryl group, an alkoxy group, an alkylthio group, an aryloxy group, a hydroxy group, or an amino group, and R and R' can combine each other to form a ring; and X represents an oxygen atom or a sulfur atom. These photographic color couplers are a novel class of two-equivalent color forming couplers which are suitable for use in color photography. A color photographic light-sensitive material containing the above described photographic color coupler and a method of forming a color image comprising developing an exposed photographic light-sensitive material in the presence of the above described photographic color coupler are also disclosed.

Inventors

  • 👤 Kozo Inouye
  • 👤 Yukio Yokota
  • 👤 Kiyoshi Nakazyo

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-31 00:25
CPC Classifications
G; G03; G03C; G03C7/00; G03C7/30; G03C7/305; G03C7/30541; C; C07; C07F; C07F9/00; C07F9/02; C07F9/06; C07F9/08; C07F9/09; C07F9/091; C07F9/12; C07F9/16; C07F9/165; C07F9/18; C07F9/22; C07F9/24; C07F9/2404; C07F9/2408; C07F9/242; C07F9/28; C07F9/38; C07F9/40; C07F9/4071; C07F9/4084; C07F9/547; C07F9/645; C07F9/6503; C07F9/65031; C07F9/6564; C07F9/6571; C07F9/6574; C07F9/65742; C07F9/6581; C07F9/6584; C07F9/65842; C07F9/65844; C07F9/65848

Claims Analysis

Total Claims: 30
Claim 1
Independent Claim 117 words
A method for forming color images which comprises developing a silver halide photographic light-sensitive material in the presence of a photographic color coupler in which a hydrogen atom at the coupling position capable of coupling with an oxidation product of an aromatic primary amine developing agent is substituted with the group represented by the following general formula: ##STR27## wherein R and R', which may be the same or different, each represents an alkyl group, an alkenyl group, an aryl group, an alkoxy group, an alkylthio group, an aryloxy group, a hydroxy group or an amino group; R and R' can combine each other to form a ring, and X represents an oxygen atom or a sulfur atom.
Claim 2
Independent Claim 117 words
A method for forming color images which comprises developing a silver halide photographic light-sensitive material in the presence of a photographic color coupler in which a hydrogen atom at the coupling position capable of coupling with an oxidation product of an aromatic primary amine developing agent is substituted with the group represented by the following general formula: ##STR27## wherein R and R', which may be the same or different, each represents an alkyl group, an alkenyl group, an aryl group, an alkoxy group, an alkylthio group, an aryloxy group, a hydroxy group or an amino group; R and R' can combine each other to form a ring, and X represents an oxygen atom or a sulfur atom.
Claim 3
Dependent Claim 75 words
The method as claimed in claim 1, wherein said coupler is represented by the following general formula (I): ##STR28## wherein A represents an image forming coupler residue containing a naphthol nucleus, a phenol nucleus, a 5-pyrazolone nucleus, a pyrazolobenzimidazole nucleus, a malondiamide nucleus or a cyanoacetanilide nucleus; the group ##STR29## is bonded to the coupling position of the coupler residue; and R, R' and X each has the same meaning as defined in claim 1.
Claim 4
Dependent Claim 127 words
The method as claimed in claim 1, wherein said coupler is represented by the following general formula (II): ##STR30## wherein A 1 represents a cyan image forming coupler residue containing a phenol nucleus or an α-naphthol nucleus, a magenta image forming coupler residue containing a 5-pyrazolone nucleus or a pyrazolobenzimidazole nucleus or a yellow image forming coupler residue containing a pivaloylacetanilide nucleus or a benzoylacetanilide nucleus; R, R' and X each has the same meaning as defined in claim 1; and R 1 represents a hydrogen atom, a halogen atom, a nitro group, a cyano group, a hydroxy group, a sulfo group, a carboxy group, an alkyl group, an alkoxy group, an aryloxy group, an acylamino group, a carbamoyl group, an oxycarbonyl group or a sulfamoyl group.
Claim 5
Dependent Claim 86 words
The method as claimed in claim 3, wherein said coupler is represented by general formula (XII): ##STR31## wherein R, R', R and X each has the same meaning as R, R', R 1 and X in general formula (II), R 3 , R 4 and R 5 each represents a hydrogen atom, a halogen atom, an alkyl group, an aryl group, an alkoxy group, an alkylthio group, a heterocyclic group, an amino group, a carbonamido group, a sulfonamido group, a sulfamoyl group or a carbamoyl group.
Claim 6
Dependent Claim 179 words
The method as claimed in claim 3, wherein said coupler is represented by general formula (XIII): ##STR32## wherein R, R' and X each has the same meaning as R, R' and X in general formula (II), R 2 represents a hydrogen atom, an alkyl group having 30 or less carbon atoms, or a carbamoyl group represented by general formulae (VII) and (VIII) described below, R 3 , R 4 , R 5 , R 6 and R 7 each represents a hydrogen atom, a halogen atom, an alkyl group, an aryl group, an alkoxy group, an alkylthio group, a heterocyclic group, an amino group, a carbonamido group, a sulfonamido group, a sulfamoyl group or a carbamoyl group, and W represents the non-metallic atomic group necessary to form a 5-membered or 6-membered ring; ##STR33## wherein Z represents a straight or branched chain alkyl group having 1 to 32 carbon atoms, a cycloalkyl group or an aryl group, and wherein Y and Y' can have the same meaning as Z, or can be represented by the formulae --OZ, --NH--Z or ##STR34##
Claim 7
Dependent Claim 60 words
The method as claimed in claim 3, wherein said coupler is represented by general formula (XIV): ##STR35## wherein R, R' and X each has the same meaning as R, R' and X in general formula (II), R 8 represents an alkyl group, an alkoxy group, a ureido group, or a substituted amino group, and R 9 represents an alkyl group.
Claim 8
Dependent Claim 65 words
The method as claimed in claim 3, wherein said coupler is represented by general formula (XV): ##STR36## wherein R, R' and X each has the same meaning as R, R' and X in general formula (II), R 10 represents an alkyl group, an alkoxy group, a ureido group, or a substituted amino group, and Q represents the atomic group necessary to form a heterocyclic ring.
Claim 9
Dependent Claim 215 words
The method as claimed in claim 3, wherein said coupler is represented by general formula (XVI): ##STR37## wherein R, R' and X each has the same meaning as R, R' and X in general formula (II), R 11 represents a hydrogen atom, a halogen atom, a nitro group, a cyano group, a hydroxy group, a sulfo group, a carboxy group, an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, an aryloxy group, an acylamino group as represented by general formulae (III) to (VI) below, a carbamoyl group as represented by general formulae (VII) or (VIII) below, an oxycarbonyl group as represented by general formula (IX) below or a sulfamoyl group as represented by general formulae (X) or (XI) below; and R 12 , R 13 , R 14 and R 15 each represents a group as defined for R 11 ; ______________________________________ NHCOZ (III) NHSO.sub.2 Z (IV) ##STR38## (V) NHCONHZ (VI) CONHZ (VII) ##STR39## (VIII) COOZ (IX) SO.sub.2NHZ (X) ##STR40## (XI) ______________________________________ wherein Z represents a straight or branched chain alkyl group having 1 to 32 carbon atoms, a cycloalkyl group or an aryl group; and Y and Y' can each have the same meaning as Z and in addition can be --OZ, --NH--Z or ##STR41##
Claim 10
Dependent Claim 239 words
The method as claimed in claim 3, wherein said coupler is represented by general formula (XVII): ##STR42## wherein R, R' and X each has the same meaning as R, R' and X in general formula (II), R 11 represents a hydrogen atom, a halogen atom, a nitro group, a cyano group, a hydroxy group, a sulfo group, a carboxy group, an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, an aryloxy group, an acylamino group as represented by general formulae (III) to (VI) below, a carbamoyl group as represented by general formulae (VII) or (VIII) below, an oxycarbonyl group as represented by general formula (IX) below or a sulfamoyl group as represented by general formulae (X) or (XI) below; and R 12 , R 13 , R 14 and R 15 each represents a group as defined for R 11 ; ______________________________________ NHCOZ (III) NHSO.sub.2 Z (IV) ##STR43## (V) NHCONHZ (VI) CONHZ (VII) ##STR44## (VIII) COOZ (IX) SO.sub.2NHZ (X) ##STR45## (XI) ______________________________________ wherein Z represents a straight or branched chain alkyl group having 1 to 32 carbon atoms, a cyaloalkyl group or an aryl group; and Y and Y' can each have the same meaning as Z and in addition can be --OZ, --NH--Z or ##STR46## and R 16 , R 17 , R 18 , R 19 R 20 each represents a group as defined for R 11 .
Claim 11
Dependent Claim 25 words
The method as claimed in claim 3, wherein said coupler is selected from the cyan dye forming two-equivalent couplers represented by the following formulae: ##STR47##
Claim 12
Dependent Claim 26 words
The method as claimed in claim 3, wherein said coupler is selected from the magenta dye image forming two-equivalent couplers as represented by the formulae: ##STR48##
Claim 13
Dependent Claim 26 words
The method as claimed in claim 3, wherein said coupler is selected from the yellow dye image forming two-equivalent couplers as represented by the formulae: ##STR49##
Claim 14
Dependent Claim 104 words
A photographic silver halide emulsion containing a photographic color coupler in which a hydrogen atom at the coupling position capable of coupling with an oxidation product of an aromatic primary amine developing agent is substituted with the group represented by the following general formula: ##STR50## wherein R and R', which may be the same or different, each represents an alkyl group, an alkenyl group, an aryl group, an alkoxy group, an alkylthio group, an aryloxy group, a hydroxy group or an amino group; R and R' can combine each other to form a ring, and X represents an oxygen atom or a sulfur atom.
Claim 15
Dependent Claim 104 words
A photographic silver halide emulsion containing a photographic color coupler in which a hydrogen atom at the coupling position capable of coupling with an oxidation product of an aromatic primary amine developing agent is substituted with the group represented by the following general formula: ##STR50## wherein R and R', which may be the same or different, each represents an alkyl group, an alkenyl group, an aryl group, an alkoxy group, an alkylthio group, an aryloxy group, a hydroxy group or an amino group; R and R' can combine each other to form a ring, and X represents an oxygen atom or a sulfur atom.
Claim 16
Dependent Claim 19 words
A photographic light-sensitive material comprising a support having thereon the photographic silver halide emulsion as claimed in claim 13.
Claim 17
Dependent Claim 135 words
A photographic light-sensitive material comprising a support having thereon a blue-sensitive silver halide emulsion layer, a green-sensitive silver halide emulsion layer and a red-sensitive silver halide emulsion layer, and at least one of the emulsion layers contains a photographic color coupler in which a hydrogen atom at the coupling position capable of coupling with an oxidation product of an aromatic primary amine developing agent is substituted with the group represented by the following general formula: ##STR51## wherein R and R', which may be the same or different, each represents an alkyl group, an alkenyl group, an aryl group, an alkoxy group, an alkylthio group, an aryloxy group, a hydroxy group or an amino group; R and R' can combine each other to form a ring, and X represents an oxygen atom or a sulfur atom.
Claim 18
Dependent Claim 135 words
A photographic light-sensitive material comprising a support having thereon a blue-sensitive silver halide emulsion layer, a green-sensitive silver halide emulsion layer and a red-sensitive silver halide emulsion layer, and at least one of the emulsion layers contains a photographic color coupler in which a hydrogen atom at the coupling position capable of coupling with an oxidation product of an aromatic primary amine developing agent is substituted with the group represented by the following general formula: ##STR51## wherein R and R', which may be the same or different, each represents an alkyl group, an alkenyl group, an aryl group, an alkoxy group, an alkylthio group, an aryloxy group, a hydroxy group or an amino group; R and R' can combine each other to form a ring, and X represents an oxygen atom or a sulfur atom.
Claim 19
Dependent Claim 30 words
A method of forming color images which comprises developing the photographic light-sensitive material as claimed in claim 14 with an aqueous alkaline solution containing a primary aromatic amine developing agent.
Claim 20
Dependent Claim 75 words
The method as claimed in claim 16, wherein said coupler is represented by the following general formula (I): ##STR52## wherein A represents an image forming coupler residue containing a naphthol nucleus, a phenol nucleus, a 5-pyrazolone nucleus, a pyrazolobenzimidazole nucleus, a malondiamide nucleus or a cyanoacetanilide nucleus; the group ##STR53## is bonded to the coupling position of the coupler residue; and R, R' and X each has the same meaning as defined in claim 1.
Claim 21
Dependent Claim 127 words
The method as claimed in claim 16, wherein said coupler is represented by the following general formula (II): ##STR54## wherein A 1 represents a cyan image forming coupler residue containing a phenol nucleus or an α-naphthol nucleus, a magenta image forming coupler residue containing a 5-pyrazolone nucleus or a pyrazolobenzimidazole nucleus or a yellow image forming coupler residue containing a pivaloylacetanilide nucleus or a benzoylacetanilide nucleus; R, R' and X each has the same meaning as defined in claim 1; and R 1 represents a hydrogen atom, a halogen atom, a nitro group, a cyano group, a hydroxy group, a sulfo group, a carboxy group, an alkyl group, an alkoxy group, an aryloxy group, an acylamino group, a carbamoyl group, an oxycarbonyl group or a sulfamoyl group.
Claim 22
Dependent Claim 86 words
The method as claimed in claim 18, wherein said coupler is represented by general formula (XII): ##STR55## wherein R, R', R and X each has the same meaning as R, R', R 1 and X in general formula (II), R 3 , R 4 and R 5 each represents a hydrogen atom, a halogen atom, an alkyl group, an aryl group, an alkoxy group, an alkylthio group, a heterocyclic group, an amino group, a carbonamido group, a sulfonamido group, a sulfamoyl group or a carbomoyl group.
Claim 23
Dependent Claim 177 words
The method as claimed in claim 18, wherein said coupler is represented by general formula (XIII): ##STR56## wherein R, R' and X each has the same meaning as R, R' and X in general formula (II), R 2 represents a hydrogen atom, an alkyl group having 30 or less carbon atoms, or a carbamoyl group represented by general formulae (VII) and (VIII) described below, R 3 , R 4 , R 5 , and R 7 each represents a hydrogen atom, a halogen atom, an alkyl group, an aryl group, an alkoxy group, an alkylthio group, a heterocyclic group, an amino group, a carbonamido group, a sulfonamido group, a sulfamoyl group or a carbamoyl group, and W represents the non-metallic atomic group necessary to form a 5-membered or 6-membered ring; ##STR57## wherein Z represents a straight or branched chain alkyl group having 1 to 32 carbon atoms, a cycloalkyl group or an aryl group, and wherein Y and Y' can have the same meaning as Z, or can be represented by the formulae --OZ, --NH-Z or ##STR58##
Claim 24
Dependent Claim 60 words
The method as claimed in claim 18, wherein said coupler is represented by general formula (XIV): ##STR59## wherein R, R' and X each has the same meaning as R, R' and X in general formula (II), R 8 represents an alkyl group, an alkoxy group, a ureido group, or a substituted amino group, and R 9 represents an alkyl group.
Claim 25
Dependent Claim 65 words
The method as claimed in claim 18, wherein said coupler is represented by general formula (XV): ##STR60## wherein R, R' and X each has the same meaning as R, R' and X in general formula (II), R 10 represents an alkyl group, an alkoxy group, a ureido group, or a substituted amino group, and Q represents the atomic group necessary to form a heterocyclic ring.
Claim 26
Dependent Claim 214 words
The method as claimed in claim 18, wherein said coupler is represented by general formula (XVI): ##STR61## wherein R, R' and X each has the same meaning as R, R' and X in general formula (II), R 11 represents a hydrogen atom, a halogen atom, a nitro group, a cyano group, a hydroxy group, a sulfo group, a carboxy group, an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, an aryloxy group, an acylamino group as represented by general formulae (III) to (VI) below, a carbamoyl group as represented by general formulae (VII) or (VIII) below, an oxycarbonyl group as represented by general formula (IX) below or a sulfamoyl group as represented by general formulae (X) or (XI) below; and R 12 , R 13 , R 14 and R 15 each represents a group as defined for R 11; ______________________________________ NHCOZ (III) NHSO.sub.2 Z (IV) ##STR62## (V) NHCONHZ (VI) CONHZ (VII) ##STR63## (VIII) COOZ (IX) SO.sub.2NHZ (X) ##STR64## (XI) ______________________________________ wherein Z represents a straight or branched chain alkyl group having 1 to 32 carbon atoms, a cycloalkyl group or an aryl group; and Y and Y' can each have the same meaning as Z and in addition can be --OZ, --NH--Z or ##STR65##
Claim 27
Dependent Claim 239 words
The method as claimed in claim 18, wherein said coupler is represented by general formula (XVII): ##STR66## wherein R, R' and X each has the same meaning as R, R' and X in general formula (II), R 11 represents a hydrogen atom, a halogen atom, a nitro group, a cyano group, a hydroxy group, a sulfo group, a carboxy group, an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, an aryloxy group, an acylamino group as represented by general formulae (III) to (VI) below, a carbamoyl group as represented by general formulae (VII) or (VIII) below, an oxycarbonyl group as represented by general formula (IX) below or a sulfamoyl group as represented by general formulae (X) or (XI) below; and R 12 , R 13 , R 14 and R 15 each represents a group as defined for R 11; ______________________________________ NHCOZ (III) NHSO.sub.2 Z (IV) ##STR67## (V) NHCONHZ (VI) CONHZ (VII) ##STR68## (VIII) COOZ (IX) SO.sub.2NHZ (X) ##STR69## (XI) ______________________________________ wherein Z represents a straight or branched chain alkyl group having 1 to 32 carbon atoms, a cyoloalkyl group or an aryl group; and Y and Y' can each have the same meaning as Z and in addition can be --OZ, --NH--Z or ##STR70## and R 16 , R 17 , R 18 , R 19 and R 20 each represents a group as defined for R 11 .
Claim 28
Dependent Claim 25 words
The method as claimed in claim 18, wherein said coupler is selected from the cyan dye forming two-equivalent couplers represented by the following formulae: ##STR71##
Claim 29
Dependent Claim 26 words
The method as claimed in claim 18, wherein said coupler is selected from the magenta dye image forming two-equivalent couplers as represented by the formulae: ##STR72##
Claim 30
Dependent Claim 26 words
The method as claimed in claim 18, wherein said coupler is selected from the yellow dye image forming two-equivalent couplers as represented by the formulae: ##STR73##

References Cited (Backward Citations)

US3770446A Cited
US3884700A Cited
US3984432A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1981-02-06 1981-08-08 1982-02-07 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1985-02-06 1985-08-08 1986-02-07 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1989-02-06 1989-08-08 1990-02-07 $7700.00 Window Closed / Lapsed

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