US4012259A
Expired / Lapsed
US
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Photographic silver halide emulsion and element and method of forming color photographic images
Assignee: Fujifilm Holdings Corp
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Filing: 1974-05-14
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Granted: 1977-03-15
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Expires: 1994-05-14
Abstract
Abstract A photographic silver halide emulsion containing a yellow color forming coupler, in which one hydrogen atom of an active methylene group is replaced by a 2,5-dioxo-1-imidazolidinyl group, in which a nitrogen atom at 3-position and a carbon atom at 4-position are connected to form a ring through a divalent aliphatic radical, a photographic element containing the emulsion and a method for forming color photographic images which comprises developing the image-exposed photographic silver halide emulsion with a primary aromatic amino developing agent. These yellow color forming couplers have a high coupling reactivity as well as no adverse effect on the bleaching of developed silver and thus they are suitable for use in rapid processing type color photographic materials.
Inventors
- 👤 Akio Okumura
- 👤 Akira Sato
- 👤 Seiji Ichijima
- 👤 Keisuke Shiba
- 👤 Kiyoshi Nakazyo
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-30 09:10
CPC Classifications
C; C07; C07D; C07D471/00; C07D471/02; C07D471/04; G; G03; G03C; G03C7/00; G03C7/30; G03C7/305; G03C7/30511; G03C7/30517; G03C7/30535
Claims Analysis
Total Claims: 37
Claim 1
Independent Claim
96 words
A method of forming color photographic images which comprises developing an image-exposed photographic silver halide emulsion layer with a primary aromatic amino developing agent in the presence of a yellow color forming coupler, said coupler having an open chain active methylene group bonded to two adjacent carbonyl groups, one of the hydrogen atoms of the active methylene group being substituted by a 2,5-dioxo-1-imidazolidinyl group, in which the nitrogen atom at the 3-position and the carbon atom at the 4-position are connected to form a ring through a divalent aliphatic group having 3 or 4 carbon atoms.
Claim 2
Independent Claim
96 words
A method of forming color photographic images which comprises developing an image-exposed photographic silver halide emulsion layer with a primary aromatic amino developing agent in the presence of a yellow color forming coupler, said coupler having an open chain active methylene group bonded to two adjacent carbonyl groups, one of the hydrogen atoms of the active methylene group being substituted by a 2,5-dioxo-1-imidazolidinyl group, in which the nitrogen atom at the 3-position and the carbon atom at the 4-position are connected to form a ring through a divalent aliphatic group having 3 or 4 carbon atoms.
Claim 3
Dependent Claim
70 words
The method of forming color photographic images as claimed in claim 1, wherein said yellow color forming coupler has the general formula (I): ##STR7##in which R represents a hydrogen atom or an alkyl group; Q represents an open chain active methylene group bonded to two adjacent carbonyl groups, one hydrogen atom of the open methylene group being eliminated; and X represents an alkylene group having 3 or 4 carbon atoms.
Claim 4
Dependent Claim
32 words
The method of forming color photographic images as claimed in claim 2, in which the open-chain methylene group represented by Q is a residue of an open-chained ketomethylene yellow color forming coupler.
Claim 5
Dependent Claim
25 words
The method of forming color photographic images as claimed in claim 2, in which said residue represented by Q is a residue of an α-acylacetamide.
Claim 6
Dependent Claim
139 words
The method of forming color photographic images as claimed in claim 2, wherein said yellow color forming coupler has the general formula (II): ##STR8##in which R represents a hydrogen atom or an alkyl group; R 1 represents an aliphatic group, an aromatic group or a heterocyclic group; R 2 represents an aromatic group or a heterocyclic group; and n represents 3 or 4, wherein R 1 , when it is said heterocyclic group, is bonded to the carbon atom of the shown carbonyl group of the acyl of said coupler through a carbon atom which forms a part of said heterocyclic group, and wherein R 2 , when it is said heterocyclic group, is bonded to the nitrogen atom of the shown amide group of said coupler through a carbon atom which forms a part of said heterocyclic group.
Claim 7
Dependent Claim
25 words
The method of forming color photographic images as claimed in claim 5, in which said aliphatic group represented by R 1 is a tert-butyl group.
Claim 8
Dependent Claim
53 words
The method of forming color photographic images as claimed in claim 5, in which said aromatic group represented by R 1 is a phenyl group or a phenyl group substituted with an electron-donating group selected from the class consisting of an alkyl group, an alkoxy group, an aryloxy group, or an amino group.
Claim 9
Dependent Claim
49 words
The method of forming color photographic images as claimed in claim 5, in which said aromatic group represented by R 2 is a phenyl group in which one of the ortho positions is substituted by a halogen atom, an alkyl group, an alkoxy group or an N-substituted amino group.
Claim 10
Dependent Claim
118 words
The method of forming color photographic images as claimed in claim 2, wherein said yellow color forming coupler has the general formula (III): ##STR9##in which R represents a hydrogen atom or an alkyl group; Z represents a halogen atom, an alkyl group, an alkoxy group; and aryloxy group or an N-substituted amino group; Y 1 , Y 2 and Y 3 each represents a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, an aryl group, an aryloxy group, an alkoxycarbonyl group, a carbamoyl group, a sulfamoyl group, an alkylamino group, an arylamino group, an acylamino group, a carboxy group, a sulfo group, a cyano group or a hydroxy group; and n represents 3 or 4.
Claim 11
Dependent Claim
149 words
The method of forming color photographic images as claimed in claim 2, wherein said yellow color forming coupler has the general formula (IV) ##STR10##in which R represents a hydrogen atom or alkyl group; Z represents a halogen atom, an alkyl group, an alkoxy group, an aryloxy group or a substituted amino group; Y 1 , Y 2 and Y 3 each represents a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, an aryl group, an aryloxy group, an alkoxycarbonyl group, a carbamoyl group, a sulfamoyl group, an alkylamino group, an arylamino group, an acylamino group, a carboxy group, a sulfo group, a cyano group, or a hydroxy group; Y 4 , Y 5 , Y 6 and Y 7 each represents a hydrogen atom, an alkyl group, an alkoxy group, an aryloxy group, an amino group or an acylamino group; and n represents 3 or 4.
Claim 12
Dependent Claim
72 words
A photographic silver halide emulsion containing a yellow color forming coupler, said coupler having an open chain active methylene group bonded to two adjacent carbonyl groups, one of the hydrogen atoms in the methylene group being substituted by a 2,5-dioxo-1-imidazolidinyl group, in which the nitrogen atom at the 3-position and the carbon atom at the 4-position are connected to form a ring through an alkylene group having 3 or 4 carbon atoms.
Claim 13
Dependent Claim
72 words
A photographic silver halide emulsion containing a yellow color forming coupler, said coupler having an open chain active methylene group bonded to two adjacent carbonyl groups, one of the hydrogen atoms in the methylene group being substituted by a 2,5-dioxo-1-imidazolidinyl group, in which the nitrogen atom at the 3-position and the carbon atom at the 4-position are connected to form a ring through an alkylene group having 3 or 4 carbon atoms.
Claim 14
Dependent Claim
68 words
The photographic silver halide emulsion as claimed in claim 11, wherein said yellow color forming coupler has the general formula (I): ##STR11##in which R represents a hydrogen atom or an alkyl group; Q represents an open chain methylene group bonded to two adjacent carbonyl groups, one of the hydrogen atoms in the methylene group is eliminated; and X represents an alkylene group having 3 or 4 carbon atoms.
Claim 15
Dependent Claim
137 words
The photographic silver halide emulsion as claimed in claim 11, wherein said yellow color forming coupler has the general formula (II) ##STR12##in which R represents a hydrogen atom or an alkyl group; R 1 represents an aliphatic group, an aromatic group or a heterocyclic group; R 2 represents an aromatic group or a heterocyclic group; and n represents 3 or 4, wherein R 1 , when it is said heterocyclic group, is bonded to the carbon atom of the shown carbonyl group of the acyl of said coupler through a carbon atom which forms a part of said heterocyclic group, and wherein R 2 , when it is said heterocyclic group, is bonded to the nitrogen atom of the shown amide group of said coupler through a carbon atom which forms a part of said heterocyclic group.
Claim 16
Dependent Claim
23 words
The photographic silver halide emulsion as claimed in claim 13, in which said aliphatic group represented by R 1 is a tert-butyl group.
Claim 17
Dependent Claim
48 words
The photographic silver halide emulsion as claimed in claim 13, in which said aromatic group represented by R 1 is a phenyl group or a phenyl group substituted with an electron-donating group selected from the class consisting of an alkyl group, an alkoxy group, or an amino group.
Claim 18
Dependent Claim
47 words
The photographic silver halide emulsion as claimed in claim 13, in which said aromatic group represented by R 2 is a phenyl group in which one of the ortho positions is substituted by a halogen atom, an alkyl group, an alkoxy group or an N-substituted amino group.
Claim 19
Dependent Claim
116 words
The photographic silver halide emulsion as claimed in claim 11, wherein said yellow color forming coupler has the general formula (III): ##STR13##in which R represents a hydrogen atom or an alkyl group; Z represents a halogen atom, an alkyl group, an alkoxy group; an aryloxy group, or an N-substituted amino group; Y 1 , Y 2 and Y 3 each represents a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, an aryl group, an aryloxy group, an alkoxycarbonyl group, a carbamoyl group, a sulfamoyl group, an alkylamino group, an arylamino group, an acylamino group, a carboxy group, a sulfo group, a cyano group or a hydroxy group; and n represents 3 or 4.
Claim 20
Dependent Claim
148 words
The photographic silver halide emulsion as claimed in claim 11, wherein said yellow color forming coupler has the general formula (IV): ##STR14##in which R represents a hydrogen atom or an alkyl group; Z represents a halogen atom, an alkyl group, an alkoxy group, an aryloxy group or a substituted amino group; Y 1 , Y 2 and Y 3 each represents a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, an aryl group, an aryloxy group, an alkoxycarbonyl group, a carbamoyl group, a sulfamoyl group, an alkylamino group, an arylamino group, an acylamino group, a carboxy group, a sulfo group, a cyano group, or a hydroxy group; Y 4 , Y 5 , Y 6 and Y 7 each represents a hydrogen atom, an alkyl group, an alkoxy group, an aryloxy group, an amino group or an acylamino group; and n represents 3 or 4.
Claim 21
Dependent Claim
18 words
The photographic silver halide emulsion as claimed in claim 11, wherein said yellow color forming coupler is α-pivaloyl-α-(2,5-dioxo-3,4-trimethylene-1-imidazolidinyl)-2'-chloro-5'-[γ-(2,4-di-tert-amylphenoxy)butyramido]acetanilide.
Claim 22
Dependent Claim
18 words
The photographic silver halide emulsion as claimed in claim 11, wherein said yellow color forming coupler is α-pivaloyl-α-(2,5-dioxo-3,4-trimethylene-1-imidazolidinyl)-2'-chloro-5'-[α-(2,4-di-tert-amylphenoxy)butyramido]acetanilide.
Claim 23
Dependent Claim
18 words
The photographic silver halide emulsion as claimed in claim 11, wherein said yellow color forming coupler is α-(4-methoxybenzoyl)-α-(2,5-dioxo-3,4-trimethylene-1-imidazolidinyl)-2'-chloro-5'-[α-(2,4-di-tert-amylphenoxy)butyramido]acetanilide.
Claim 24
Dependent Claim
18 words
The photographic silver halide emulsion as claimed in claim 11, wherein said yellow color forming coupler is α-(2-methylbenzoyl)-α-(2,5-dioxo-3,4-trimethylene-1-imidazolidinyl)-2'-chloro-5'-hexadecyloxycarbonylacetanilide.
Claim 25
Dependent Claim
19 words
A photographic light-sensitive material which comprises a support having thereon the silver halide emulsion as claimed in claim 12.
Claim 26
Dependent Claim
69 words
The photographic light-sensitive material as claimed in claim 23, wherein said yellow color forming coupler has the general formula (I): ##STR15##in which R represents a hydrogen atom or an alkyl group; Q represents an open chain methylene group bonded to two adjacent carbonyl groups in which one hydrogen atom attached to an active methylene group is eliminated; and X represents an alkylene group having 3 or 4 carbon atoms.
Claim 27
Dependent Claim
136 words
The photographic light-sensitive material as claimed in claim 23, wherein said yellow color forming coupler has the general formula (II): ##STR16##in which R represents a hydrogen atom or an alkyl group; R 1 represents an aliphatic group, an aromatic group or a heterocyclic group; R 2 represents an aromatic group or a heterocyclic group; and n represents 3 or 4, wherein R 1 , when it is said heterocyclic group, is bonded to the carbon atom of the shown carbonyl group of the acyl of said coupler through a carbon atom which forms a part of said heterocyclic group, and wherein R 2 , when it is said heterocyclic group, is bonded to the nitrogen atom of the shown amide group of said coupler through a carbon atom which forms a part of said heterocyclic group.
Claim 28
Dependent Claim
115 words
The photographic light-sensitive material as claimed in claim 23, wherein said yellow color forming coupler has the general formula (III): ##STR17##in which R represents a hydrogen atom or an alkyl group; Z represents a halogen atom, an alkyl group, an alkoxy group; an aryloxy group or an N-substituted amino group; Y 1 , Y 2 and Y 3 each represents a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, an aryl group, an aryloxy group, an alkoxycarbonyl group, a carbamoyl group, a sulfamoyl group, an alkylamino group, an arylamino group, an acylamino group, a carboxy group, a sulfo group, a cyano group or a hydroxy group; and n represents 3 or 4.
Claim 29
Dependent Claim
148 words
The photographic light-sensitive material as claimed in claim 23, wherein said yellow color forming coupler has the general formula (IV): ##STR18## in which R represents a hydrogen atom or an alkyl group; Z represents a halogen atom, an alkyl group, a alkoxy group, an aryloxy group or a substituted amino group; Y 1 , Y 2 and Y 3 each represents a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, an aryl group, an aryloxy group, an alkoxycarbonyl group, a carbamoyl group, a sulfamoyl group, an alkylamino group, an arylamino group, an acylamino group, a carboxy group, a sulfo group, a cyano group, or a hydroxy group; Y 4 , Y 5 , Y 6 and Y 7 each represents a hydrogen atom, an alkyl group, an alkoxy group, an aryloxy group, an amino group or an acylamino group; and n represents 3 or 4.
Claim 30
Dependent Claim
76 words
The method of forming color photographic images as claimed in claim 5, wherein said heterocyclic group is selected from the class consisting of a heterocyclic group of the thiophane series, the furan series, the pyran series, the chromene series, the pyrrole series, the pyrazole series, the pyridine series, the pyrazine series, the pyrimidine series, the pyridazine series, the indolizinyl series, the thiazole series, the imidazole series, the oxazole series, a 1,3,5-triazine series, and the oxazine series.
Claim 31
Dependent Claim
69 words
The photographic silver halide emulsion as claimed in claim 13, wherein said heterocyclic group is selected from heterocyclic groups of the thiophane series, the furan series, the pyran series, the chromene series, the pyrrole series, the pyrazole series, the pyridine series, the pyrazine series, the pyrimidine series, the pyridazine series, the indolizinyl series, the thiazole series, the imidazole series, the oxazole series, a 1,3,5-triazine series, and the oxazine series.
Claim 32
Dependent Claim
68 words
The photographic light-sensitive material as claimed in claim 25, wherein said heterocyclic group is selected from heterocyclic groups of the thiophane series, the furan series, the pyran series, the chromene series, the pyrrole series, the pyrazole series, the pyridine series, the pyrazine series, the pyrimidine series, the pyridazine series, the indolizinyl series, the thiazole series, the imidazole series, the oxazole series, a 1,3,5-triazine series, and the oxazine series.
Claim 33
Dependent Claim
24 words
The photographic silver halide emulsion as claimed in claim 12, in which said residue represented by Q is a residue of an α -acylacetamide.
Claim 34
Dependent Claim
23 words
The photographic light-sensitive material as claimed in claim 24, in which said residue represented by Q is a residue of an α -acylacetamide.
Claim 35
Dependent Claim
24 words
The method of claim 4, wherein said alkylene group is represented by the formula (CH 2 ) n wherein n represents 3 or 4.
Claim 36
Dependent Claim
29 words
The photographic silver halide emulsion as claimed in claim 31, wherein said alkylene group is represented by the formula (CH 2 ) n wherein n represents 3 or 4.
Claim 37
Dependent Claim
29 words
The photographic silver halide emulsion as claimed in claim 32, wherein said alkylene group is represented by the formula (CH 2 ) n wherein n represents 3 or 4.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1980-03-14 | 1980-09-13 | 1981-03-15 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-03-14 | 1984-09-13 | 1985-03-15 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-03-14 | 1988-09-13 | 1989-03-15 | $7700.00 | Window Closed / Lapsed |