US4439513A
Expired / Lapsed
US
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Color photographic light-sensitive material with naphthol redox dye releaser
Assignee: Fujifilm Holdings Corp
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Filing: 1982-12-28
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Granted: 1984-03-27
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Expires: 2002-12-28
Abstract
Abstract A color photographic light-sensitive material is disclosed. The material is comprised of a support having thereon a layer containing at least one kind of dye releasing 2-acylamino-1-naphthol derivative represented by the following general formula (I): R--L--D (I) wherein R represents a reducing group represented by the following general formula (II): ##STR1## wherein the substituents R 1 -R 8 are defined within the application; L represents a connecting group between R and D wherein specific examples of L are defined in the specification; and D represents a dye or a precursor of a dye. The dye releasing 2-acylamino-1-naphthol derivative of the present invention has a high dye releasing efficiency when it is oxidized. The derivative of the invention can release a dye having a good diffusibility and can provide a high dye transfer density and thus it is suitable to use as a coloring material in a color photographic light-sensitive material of diffusion transfer type. A method of forming a color image using the color photographic light-sensitive material is also disclosed.
Inventors
- 👤 Kozo Sato
- 👤 Shinsaku Fujita
- 👤 Hideki Naito
- 👤 Hiroshi Hara
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-04 08:21
CPC Classifications
G; G03; G03C; G03C8/00; G03C8/02; G03C8/08; G03C8/10
Claims Analysis
Total Claims: 28
Claim 1
Independent Claim
446 words
A silver halide color photographic light-sensitive material comprising a support having thereon a layer containing at least one kind of dye releasing 2-acylamino-1-naphthol derivative represented by the following general formula (I): R--L--D (I) wherein R represents a reducing group represented by the following general formula (II): ##STR27## wherein R 1 represents a hydrogen atom or an acyl group having 1 to 12 carbon atoms; R 2 to R 8 , which may be the same or different, each represents a hydrogen atom or a substituent selected from an alkyl group, a cycloalkyl group, an alkenyl group, an aryl group, an alkoxy group, an aryloxy group, an aralkyl group, an acylamino group, an alkylamino group, a dialkylamino group, an arylamino group, a diarylamino group, a halogen atom, an acyloxy group, a hydroxy group, a carboxy group, a cyano group, an acyl group, a carbamoyl group, a substituted carbamoyl group, a sulfamoyl group, a substituted sulfamoyl group, a sulfamoylamino group, a substituted sulfamoylamino group, a ureido group, a substituted ureido group, an alkylsulfonyl group, an arylsulfonyl group, an alkylsulfonylamino group, an arylsulfonylamino group, a sulfamoylamino group, a substituted sulfamoylamino group and a nitro group, and the alkyl moiety or the aryl moiety in the above described substituents may be further substituted with an alkoxy group, an aryloxy group, an acyloxy group, a halogen atom, a hydroxy group, a carboxy group, a cyano group, an acyl group, a sulfamoyl group, a substituted sulfamoyl group, a carbamoyl group, a substituted carbamoyl group, an acylamino group, a ureido group, a substituted ureido group, an alkylsulfonyl group, an arylsulfonyl group, an alkylsulfonylamino group or an arylsulfonylamino group, the groups represented by R 2 , R 3 , R 4 or R 5 may contain up to 12 carbon atoms, and groups represented by R 6 , R 7 or R 8 may contain up to 22 carbon atoms and at least one of them should contain not smaller than 8 carbon atoms; L represents a divalent connecting group between R and D selected from the group represented by the following formulae: ##STR28## wherein R, R', R" and R"', which may be the same or different, each represents a hydrogen atom or a substituent selected from a methyl group, an ethyl group, a hydroxymethyl group, a methoxymethyl group, a carboxymethyl group, a cyanomethyl group, a hydroxyethyl group, a methoxyethyl group, a carboxyethyl group and a cyanoethyl group; the benzene ring may be further substituted with an alkyl group, an alkoxy group, a halogen atom or a hydroxy group; and X represents --O--, --S--, ##STR29## (wherein R has the same meaning as defined above); and D represents a dye or a precursor of dye.
Claim 2
Dependent Claim
446 words
A silver halide color photographic light-sensitive material comprising a support having thereon a layer containing at least one kind of dye releasing 2-acylamino-1-naphthol derivative represented by the following general formula (I): R--L--D (I) wherein R represents a reducing group represented by the following general formula (II): ##STR27## wherein R 1 represents a hydrogen atom or an acyl group having 1 to 12 carbon atoms; R 2 to R 8 , which may be the same or different, each represents a hydrogen atom or a substituent selected from an alkyl group, a cycloalkyl group, an alkenyl group, an aryl group, an alkoxy group, an aryloxy group, an aralkyl group, an acylamino group, an alkylamino group, a dialkylamino group, an arylamino group, a diarylamino group, a halogen atom, an acyloxy group, a hydroxy group, a carboxy group, a cyano group, an acyl group, a carbamoyl group, a substituted carbamoyl group, a sulfamoyl group, a substituted sulfamoyl group, a sulfamoylamino group, a substituted sulfamoylamino group, a ureido group, a substituted ureido group, an alkylsulfonyl group, an arylsulfonyl group, an alkylsulfonylamino group, an arylsulfonylamino group, a sulfamoylamino group, a substituted sulfamoylamino group and a nitro group, and the alkyl moiety or the aryl moiety in the above described substituents may be further substituted with an alkoxy group, an aryloxy group, an acyloxy group, a halogen atom, a hydroxy group, a carboxy group, a cyano group, an acyl group, a sulfamoyl group, a substituted sulfamoyl group, a carbamoyl group, a substituted carbamoyl group, an acylamino group, a ureido group, a substituted ureido group, an alkylsulfonyl group, an arylsulfonyl group, an alkylsulfonylamino group or an arylsulfonylamino group, the groups represented by R 2 , R 3 , R 4 or R 5 may contain up to 12 carbon atoms, and groups represented by R 6 , R 7 or R 8 may contain up to 22 carbon atoms and at least one of them should contain not smaller than 8 carbon atoms; L represents a divalent connecting group between R and D selected from the group represented by the following formulae: ##STR28## wherein R, R', R" and R"', which may be the same or different, each represents a hydrogen atom or a substituent selected from a methyl group, an ethyl group, a hydroxymethyl group, a methoxymethyl group, a carboxymethyl group, a cyanomethyl group, a hydroxyethyl group, a methoxyethyl group, a carboxyethyl group and a cyanoethyl group; the benzene ring may be further substituted with an alkyl group, an alkoxy group, a halogen atom or a hydroxy group; and X represents --O--, --S--, ##STR29## (wherein R has the same meaning as defined above); and D represents a dye or a precursor of dye.
Claim 3
Dependent Claim
50 words
A color photographic light-sensitive material as claimed in claim 1, wherein the reducing group represented by R has an oxidation reduction potential to a saturated calomel electrode of 1.2 v or less measuring the polarographic half wave potential using acetonitrile as a solvent and sodium perchlorate as a supporting electrolyte.
Claim 4
Dependent Claim
21 words
A color photographic light-sensitive material as claimed in claim 1, wherein the reducing group represented by R contains a ballast group.
Claim 5
Dependent Claim
24 words
A color photographic light-sensitive material as claimed in claim 3, wherein the ballast group is a hydrophobic group containing 10 or more carbon atoms.
Claim 6
Dependent Claim
47 words
A color photographic light-sensitive material as claimed in claim 1, wherein the divalent connecting group represented by L is a group which bonds to the reducing group represented by R through an oxygen atom and contains a total number of carbon atoms of not more than 12.
Claim 7
Dependent Claim
55 words
A color photographic light-sensitive material as claimed in claim 1, wherein the dye portion represented by D is selected from the group of dyes consisting of an azo dye, an azomethine dye, an anthraquinone dye, a naphthoquinone dye, a styryl dye, a quinophthalone dye, an indigoid dye, a carbonium ion dye or a phthalocyanine dye.
Claim 8
Dependent Claim
285 words
A color photographic light-sensitive material as claimed in claim 6, wherein the dye included in the dye portion represented by D is selected from the group of dyes having the following general formulae: ##STR30## wherein R 11 to R 16 , which may be the same or different, each represents a hydrogen atom or a substituent selected from the group consisting of an alkyl group having 1 to 12 carbon atoms, a cycloalkyl group having 5 to 12 carbon atoms, an aralkyl group having 7 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, an aryloxy group having 6 to 12 carbon atoms, an aryl group having 6 to 12 carbon atoms, an acylamino group having 1 to 22 carbon atoms, an acyl group having 1 to 12 carbon atoms, a cyano group, a hydroxy group, an alkylsulfonylamino group having 1 to 12 carbon atoms, an arylsulfonylamino group having 6 to 12 carbon atoms, an alkylsulfonyl group having 1 to 12 carbon atoms, a hydroxyalkyl group having 1 to 12 carbon atoms, a cyanoalkyl group having 2 to 12 carbon atoms, an alkoxycarbonylalkyl group having 3 to 12 carbon atoms, an alkoxyalkyl group having 2 to 12 carbon atoms, an aryloxyalkyl group having 7 to 12 carbon atoms, a nitro group, a halogen atom, a sulfamoyl group, an N-substituted sulfamoyl group having 1 to 12 carbon atoms, a carbamoyl group, an N-substituted carbamoyl group having 1 to 12 carbon atoms, an acyloxyalkyl group having 2 to 12 carbon atoms, an amino group, a substituted amino group having 1 to 12 carbon atoms, an alkylthio group having 1 to 12 carbon atoms, and an arylthio group having 6 to 12 carbon atoms.
Claim 9
Dependent Claim
30 words
A color photographic light-sensitive material as claimed in claim 1, wherein the dye portion represented by D does not contain a group which hinders tinting of an image receiving sheet.
Claim 10
Dependent Claim
37 words
A color photographic light-sensitive material as claimed in claim 1, wherein the light-sensitive silver halide is selected from the group consisting of silver chloride, silver chlorobromide, silver chloroiodide, silver bromide, silver iodobromide, silver chloroiodobromide or silver iodide.
Claim 11
Dependent Claim
57 words
A color photographic light-sensitive material as claimed in claim 1, wherein the color photographic light-sensitive material comprises a transparent support having thereon an image receiving layer, a substantially opaque light reflective layer, a layer containing at least one kind of the dye releasing 2-acylamino-1-naphthol derivative represented by the general formula (I), a light-sensitive silver halide emulsion layer.
Claim 12
Dependent Claim
23 words
A color photographic light-sensitive material as claimed in claim 1, wherein the color photographic light-sensitive material is a heat-developable color photographic light-sensitive material.
Claim 13
Dependent Claim
23 words
A color photographic light-sensitive material as claimed in claim 1, wherein the color photographic light-sensitive material is a heat-developable color photographic light-sensitive material.
Claim 14
Dependent Claim
28 words
A color photographic light-sensitive material as claimed in claim 1, further comprising a layer containing a light-sensitive silver halide, an organic silver salt oxidizing agent, and a binder.
Claim 15
Dependent Claim
21 words
A color photographic light-sensitive material as claimed in claim 1, wherein the color photographic light-sensitive material further contains a reducing agent.
Claim 16
Dependent Claim
37 words
A color photographic light-sensitive material as claimed in claim 1, wherein an amount of the dye releasing compound represented by the general formula (I) is from 0.01 mol to 10 mols per mol of silver contained therein.
Claim 17
Dependent Claim
31 words
A color photographic light-sensitive material as claimed in claim 15, wherein an amount of the dye releasing compound is from 0.01 mol to 1 mol per mol of silver contained therein.
Claim 18
Dependent Claim
38 words
A color photographic light-sensitive material as claimed in claim 13, wherein the organic silver salt oxidizing agent is a silver salt of an aliphatic or aromatic carboxylic acid or a silver salt of a nitrogen containing heterocyclic compound.
Claim 19
Dependent Claim
22 words
A color photographic light-sensitive material as claimed in claim 13, wherein the color photographic light-sensitive material further contains a dye releasing accelerator.
Claim 20
Dependent Claim
34 words
A color photographic light-sensitive material as claimed in claim 18, wherein the dye releasing accelerator is a compound which nucleophilically attacks an oxidized product of the dye releasing compound to release a diffusible dye.
Claim 21
Dependent Claim
33 words
A color photographic light-sensitive material as claimed in claim 18, wherein the dye releasing accelerator is selected from the group consisting of a base, a base releasing agent and a water releasing compound.
Claim 22
Dependent Claim
15 words
A color photographic light-sensitive material as claimed in claim 13, wherein the binder is gelatin.
Claim 23
Independent Claim
478 words
A method of forming a color image comprising: (1) imagewise exposing a silver halide color photographic light-sensitive material comprising a support having thereon a layer containing at least one kind of dye releasing 2-acylamino-1-naphthol derivative represented by the following general formula (I): R--L--D (I) wherein R represents a reducing group represented by the following general formula (II): ##STR31## wherein R 1 represents a hydrogen atom or an acyl group having 1 to 12 carbon atoms; R 2 to R 8 , which may be the same or different, each represents a hydrogen atom or a substituent selected from an alkyl group, a cycloalkyl group, an alkenyl group, an aryl group, an alkoxy group, an aryloxy group, an aralkyl group, an acylamino group, an alkylamino group, a dialkylamino group, an arylamino group, a diarylamino group, a halogen atom, an acyloxy group, a hydroxy group, a carboxy group, a cyano group, an acyl group, a carbonyl group, a substituted carbamoyl group, a sulfamoyl group, a substituted sulfamoyl group, a sulfamoylamino group, a substituted sulfamoylamino group, a ureido group, a substituted ureido group, an alkylsulfonyl group, an arylsulfonyl group, an alkylsulfonylamino group, an arylsulfonylamino group, a sulfamoylamino group, a substituted sulfamoylamino group and a nitro group, and the alkyl moiety or the aryl moiety in the above described substituents may be further substituted with an alkoxy group, an aryloxy group, an acyloxy group, a halogen atom, a hydroxy group, a carboxy group, a cyano group, an acyl group, a sulfamoyl group, a substituted sulfamoyl group, a carbamoyl group, a substituted carbamoyl group, an acylamino group, a ureido group, a substituted ureido group, an alkylsulfonyl group, an arylsulfonyl group, an alkylsulfonylamino group or an arylsulfonylamino group; the groups represented by R 2 , R 3 , R 4 or R 5 may contain up to 12 carbon atoms, and groups represented by R 6 , R 7 or R 8 may contain up to 22 carbon atoms and at least one of them should contain not smaller than 8 carbon atoms; L represents a divalent connecting group between R and D selected from the group represented by the following formulae: ##STR32## wherein R, R', R" and R"', which may be the same or different, each represents a hydrogen atom or a substituent selected from a methyl group, an ethyl group, a hydroxymethyl group, a methoxymethyl group, a carboxymethyl group, a cyanomethyl group, a hydroxyethyl group, a methoxyethyl group, a carboxyethyl group and a cyanoethyl group; the benzene ring may be further substituted with an alkyl group, an alkoxy group, a halogen atom or a hydroxy group; and X represents --O--, --S--, ##STR33## (wherein R has the same meaning as defined above); and D represents a dye or a precursor of dye, (2) developing the exposed photographic material to release a diffusible dye and diffusing the diffusible dye into a dye receiving layer.
Claim 24
Independent Claim
478 words
A method of forming a color image comprising: (1) imagewise exposing a silver halide color photographic light-sensitive material comprising a support having thereon a layer containing at least one kind of dye releasing 2-acylamino-1-naphthol derivative represented by the following general formula (I): R--L--D (I) wherein R represents a reducing group represented by the following general formula (II): ##STR31## wherein R 1 represents a hydrogen atom or an acyl group having 1 to 12 carbon atoms; R 2 to R 8 , which may be the same or different, each represents a hydrogen atom or a substituent selected from an alkyl group, a cycloalkyl group, an alkenyl group, an aryl group, an alkoxy group, an aryloxy group, an aralkyl group, an acylamino group, an alkylamino group, a dialkylamino group, an arylamino group, a diarylamino group, a halogen atom, an acyloxy group, a hydroxy group, a carboxy group, a cyano group, an acyl group, a carbonyl group, a substituted carbamoyl group, a sulfamoyl group, a substituted sulfamoyl group, a sulfamoylamino group, a substituted sulfamoylamino group, a ureido group, a substituted ureido group, an alkylsulfonyl group, an arylsulfonyl group, an alkylsulfonylamino group, an arylsulfonylamino group, a sulfamoylamino group, a substituted sulfamoylamino group and a nitro group, and the alkyl moiety or the aryl moiety in the above described substituents may be further substituted with an alkoxy group, an aryloxy group, an acyloxy group, a halogen atom, a hydroxy group, a carboxy group, a cyano group, an acyl group, a sulfamoyl group, a substituted sulfamoyl group, a carbamoyl group, a substituted carbamoyl group, an acylamino group, a ureido group, a substituted ureido group, an alkylsulfonyl group, an arylsulfonyl group, an alkylsulfonylamino group or an arylsulfonylamino group; the groups represented by R 2 , R 3 , R 4 or R 5 may contain up to 12 carbon atoms, and groups represented by R 6 , R 7 or R 8 may contain up to 22 carbon atoms and at least one of them should contain not smaller than 8 carbon atoms; L represents a divalent connecting group between R and D selected from the group represented by the following formulae: ##STR32## wherein R, R', R" and R"', which may be the same or different, each represents a hydrogen atom or a substituent selected from a methyl group, an ethyl group, a hydroxymethyl group, a methoxymethyl group, a carboxymethyl group, a cyanomethyl group, a hydroxyethyl group, a methoxyethyl group, a carboxyethyl group and a cyanoethyl group; the benzene ring may be further substituted with an alkyl group, an alkoxy group, a halogen atom or a hydroxy group; and X represents --O--, --S--, ##STR33## (wherein R has the same meaning as defined above); and D represents a dye or a precursor of dye, (2) developing the exposed photographic material to release a diffusible dye and diffusing the diffusible dye into a dye receiving layer.
Claim 25
Dependent Claim
23 words
A method of forming a color image as claimed in claim 22, wherein the development is carried out using an alkaline processing solution.
Claim 26
Dependent Claim
20 words
A method of forming a color image as claimed in claim 22, wherein the development is carried out by heating.
Claim 27
Dependent Claim
26 words
A method of forming a color image as claimed in claim 22, wherein the diffusible dye is transferred into an image receiving layer containing a mordant.
Claim 28
Dependent Claim
25 words
A method of forming a color image as claimed in claim 22, wherein the diffusible dye is transferred into a support which is dye acceptable.
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) | 1987-03-27 | 1987-09-26 | 1988-03-27 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1991-03-27 | 1991-09-26 | 1992-03-27 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1995-03-27 | 1995-09-26 | 1996-03-27 | $7700.00 | Window Closed / Lapsed |