USH156H - Silver halide color light-sensitive material - Google Patents

Silver halide color light-sensitive material Download PDF

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Publication number
USH156H
USH156H US06/783,505 US78350585A USH156H US H156 H USH156 H US H156H US 78350585 A US78350585 A US 78350585A US H156 H USH156 H US H156H
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Prior art keywords
group
coupler
sensitive material
silver halide
silver
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US06/783,505
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Inventor
Takashi Ozawa
Tsumoru Hirano
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Fujifilm Holdings Corp
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Fuji Photo Film Co Ltd
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Assigned to FUJI PHOTO FILM CO., LTD. NO. 210, NAKANUMA, MINAMI ASHIGARA-SHI, KANAGAWA, JAPAN reassignment FUJI PHOTO FILM CO., LTD. NO. 210, NAKANUMA, MINAMI ASHIGARA-SHI, KANAGAWA, JAPAN ASSIGNMENT OF ASSIGNORS INTEREST. Assignors: HIRANO, TSUMORU, OZAWA, TAKASHI
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    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
    • G03C7/00—Multicolour photographic processes or agents therefor; Regeneration of such processing agents; Photosensitive materials for multicolour processes
    • G03C7/30—Colour processes using colour-coupling substances; Materials therefor; Preparing or processing such materials
    • G03C7/32—Colour coupling substances
    • G03C7/327—Macromolecular coupling substances
    • G03C7/3275—Polymers obtained by reactions involving only carbon-to-carbon unsaturated bonds, e.g. vinyl polymers
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
    • G03C7/00—Multicolour photographic processes or agents therefor; Regeneration of such processing agents; Photosensitive materials for multicolour processes
    • G03C7/30—Colour processes using colour-coupling substances; Materials therefor; Preparing or processing such materials
    • G03C7/32—Colour coupling substances
    • G03C7/36—Couplers containing compounds with active methylene groups
    • G03C7/38—Couplers containing compounds with active methylene groups in rings

Definitions

  • the present invention relates to a silver halide color light-sensitive material, and more particularly to a reversal color light-sensitive material which has excellent properties for a sensitization treatment.
  • the silver halide color light-sensitive materials typically resort to subtractive color reproduction using three primary colors.
  • the color image is formed by the combination of three dyes derived from a yellow color-forming coupler, a magenta color-forming coupler, and a cyan color-forming coupler.
  • magenta color-forming couplers nitrogen-containing heterocyclic compounds such as 5-pyrazolones are in general use. Such couplers have some disadvantages. Particularly, they are liable to restrain development. An emulsion layer containing such a coupler tends to be less sensitive and to yield a softer gradation than an emulsion layer of the same sensitivity and gradation containing a phenol-type coupler, naphthol-type coupler, and acetanilide-type coupler. Thus it is necessary to increase the sensitivity and gradation of the emulsion layer containing a magenta coupler and to control the amount of the emulsion to be applied in order to establish proper color balance. At a result, the magenta image tends to be inferior in graininess and sharpness to the other color images.
  • magenta image of poor graininess is fatal to the light-sensitive material.
  • the tendency toward low sensitivity is a disadvantage in sensitization treatment which is carried out in reversal color development as noted in Example 1 in order to raise the sensitivity by extending the usual development time of the first development or the black-and-white development.
  • the tendency toward low sensitivity destroys the color balance of yellow color-forming, magenta color-forming and cyan color-forming in the sensitization treatment.
  • reversal color light-sensitive materials containing such above-mentioned magenta couplers have poor properties for the sensitization treatment. This is a fatal drawback for reversal color light-sensitive materials, which must often undergo a sensitization treatment.
  • One object of this invention is to provide a color light-sensitive material having high sensitivity.
  • Another object of this invention is to provide a reversal color light-sensitive material which has excellent properties for a sensitization treatment.
  • Still another object of this invention is to provide a color light-sensitive material which is superior in graininess.
  • a silver halide color light-sensitive material which contains a polymer coupler having a number average molecular weight higher than 30,000 and having a polymeric unit derived from a monomeric magenta coupler represented by formula (I): ##STR2## wherein R 1 is hydrogen, chlorine, or a lower alkyl group having 1 to 4 carbon atoms; A is a phenylene group, a --CONH-- group, or a --COO-- group; B is an unsubstituted or substituted alkylene group which may be either linear or branched, an unsubstituted or substituted aralkylene group, or an unsubstituted or substituted phenylene group; Y is --OH--, --NH--, --S--, --SO--, --SO 2 --, --CONH--, --COO--, --NHCO--, or --NHCONH--; Q is a residue of a magenta color-forming couple
  • B is an unsubstituted or substitued alkylene group having 1 to 10 carbon atoms which may be either linear of branched, an unsubsituted or substituted aralkylene group, or an unsubstituted or substituted phenylene group.
  • the alkylene group includes, for example, methylene, methylmethylene, dimethylmethylene, dimethylene, trimethylene, tetramethylene, pentamethylene, hexamethylene, and decylmethylene.
  • the aralkylene group includes, for example, benzilidene.
  • the phenylene group includes, for example, p-phenylene, m-phenylene, and methylphenylene.
  • the substituent of the alkylene, aralkylene, or phenylene group represented by B can include an aryl group (e.g., a phenyl group), a nitro group, a hydroxyl group, a cyano group, a sulfo group, an alkoxy group (e.g., a methoxy group), an aryloxy group (e.g., a phenoxy group), an acyloxy group (e.g., an acetoxy group) an acylamino group (e.g., an acetylamino group), a sulfonamido group (e.g., a methanesulfonamido group), a sulfamoyl group (e.g., a methylsulfamoyl group), a halogen atom (e.g., a fluorine atom, a chlorine atom, and a bormine atom), a carboxy
  • the residue of the magenta color-forming coupler represented by Q is preferably of pyrazolone type, pyrazolotriazole type, or imidazopyrazole type. Examples of useful residues are represented as follows. ##STR3##
  • the pyrazolo[1,5-b][1,2,4]triazole residue represented by formula (7) is excellent because of less side-absorption of yellow color of the resulting dye and high light fastness.
  • R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and R 8 each represents a hydrogen atom, a hydroxyl group, an unsubstituted or substituted alkyl group (preferably having from 1 to 20 carbon atoms, such as a methyl group, a propyl group, a t-butyl groups, a trifluoromethyl group, and a tridecyl group), an aryl group (preferably having from 6 to 20 carbon atoms, such as a phenyl group, a 4-t-butylphenyl group, a 2,4-di-t-aminophenyl group, and a 4-methoxyphenyl group), a heterocyclic group (e.g., a 2-furyl group, a 2-thienyl group, a 2-pyrimidinyl group, and a 2-benzothiazolyl group), an alkylamino group (preferably having from 1 to 20 carbon
  • X denotes a hydrogen atom or an elimination group bonded to the coupling position through an oxygen atom, a nitrogen atom, or a sulfur atom.
  • X is bonded to the coupling position through an oxygen atom, a nitrogen atom, or a sulfur atom
  • such an atom is bonded to an alkyl group, an aryl group, an alkylsulfonyl group, an arylsulfonyl group, an alkylcarbonyl group, an arylcarbonyl group, or a heterocyclic group.
  • said alkyl group, aryl group, and heterocyclic group may have a substituent.
  • substituents include, for example, an alkyl group (e.g., a methyl group and an ethyl group), an alkoxy group (e.g., a methoxy group and an ethoxy group), an aryloxy group (e.g., a phenyloxy group), an alkoxycarbonyl group (e.g., a methoxycarbonyl group), an acylamino group (e.g., an acetylamino group), a carbamoyl group, an alkylcarbamoyl group (e.g., a methylcarbamoyl group and an ethylcarbamoyl group), a dialkylcarbamoyl group (e.g., a dimethylcarbamoyl group), an arylcarbamoyl group (e.g., a phenylcarbamoyl group), an alkylsulfonyl group (e.
  • substituents are a halogen atom, an alkyl group, an alkoxy group, an alkoxycarbonyl group, and a cyano group.
  • the group bonded to a nitrogen atom includes any group that contains the nitrogen atom and forms a five- or six-membered ring and that can be an elimination group (e.g., an imidazolyl group, a pyrazolyl group, a triazolyl group, and a tetrazolyl group).
  • those in which the 1-phenyl group thereof has chlorine atoms at the 2-, 4- and 6-positions thereof give a most excellent graininess, and therefore, they are more preferable than those in which the 1-phenyl group thereof has chlorine atoms at the 2- and 5-positions thereof.
  • the polymer coupler preferably has a number average molecular weight higher than 45,000 and more preferably higher than 80,000, but lower than 1,000,000 and more preferably lower than 500,000.
  • the polymer coupler is used in an amount of from 2 ⁇ 10 -3 mol to 5 ⁇ 10 -1 mol, and preferably more than 1 ⁇ 10 -2 mol, as a color-forming unit, per mol of silver.
  • the polymer coupler of the present invention may be a homopolymer of the monomeric coupler represented by formula (I) or a copolymer between monomer coupler (I) and an ethylenically unsaturated monomeric coupler which does not couple with an oxidation product of an aromatic primary amine developer (and therefore forms no color).
  • two or more monomeric coupler included within formula (I) may be used as monomeric coupler (I).
  • esters or amides drived from acrylic acid, ⁇ -chloroacrylic acid, ⁇ -alkyl acrylic acids e.g.
  • methacrylic acid etc.
  • methacrylic acid etc.
  • the like e.g., ethyl acrylate, n-propyl acrylate, n-butyl acrylate, t-butyl acrylate, iso-butyl acrylate, 2-ethylhexyl acrylate, cyclohexyl acrylate, methyl methacrylate, ethyl methacrylate, n-butyl methacrylate, n-butylacrylamide, t-butylacrylamide, diacetoneacrylamide and n-butylmethacrylamide), vinyl esters (e.g., vinyl acetate and vinyl propionate), styrene and the like.
  • acrylates and metahcrylates are preferably used.
  • the non-color forming ethyleneically unsaturated monomer used here may be used together with two kinds or more.
  • the combinations of ethyl acrylate and n-butyl acrylate, n-butyl acrylate and styrene, and methyl methacrylate and diacetoneacrylamide may be used.
  • the ethylenically unsaturated monomer which is used to copolymerize with the monomeric coupler represented by the above-described general formula (I) can be selected so that the copolymer to be formed possesses good physical properties and/or chemical properties, for example, solubility, compatibility with a binder such as gelatin in a photographic colloid composition, flexibility, heat stability, etc., as well known in the field of polymer color couplers.
  • the polymer coupler used in this invention is oleophilic and, in particular, preferably used in a latex form.
  • the free redical polymerization of the ethylenically unsaturated monomer is initiated with the addition to the monomer molecule of a free radical which is formed by thermal decomposition of a chemical polymerization initiator or a physical action, e.g., irradiation of ultraviolet rays or other high energy radiations, high frequencies, etc.
  • main chemical polymerization initiators examples include azobis type polymerization initiators (e.g., dimethyl 2,2'-azobisisobutyrate, diethyl 2,2'-azobisisobutyrate, 2,2'-azobisisobutyronitrile, 2,2'-azobis-(2,4-dimethylvalenonitrile), etc.), benzoyl peroxide, chlorobenzoyl peroxide and other compounds.
  • azobis type polymerization initiators e.g., dimethyl 2,2'-azobisisobutyrate, diethyl 2,2'-azobisisobutyrate, 2,2'-azobisisobutyronitrile, 2,2'-azobis-(2,4-dimethylvalenonitrile), etc.
  • benzoyl peroxide chlorobenzoyl peroxide and other compounds.
  • Organic solvents which can be used in polymerization of the oleophilic polymer couplers are preferably those which can usually be admixed with monomers to be used without limitation, are good solvent for the oleophilic polymer coupler formed, do not react with initiators to be used and do not interrupt usual actions in free radical addition polymerization.
  • organic solvent examples include aromatic hydrocarbons (e.g., benzene, toluene, etc.), hydrocarbons (e.g., n-hexane, etc.), alchohols (e.g., methanol, ethanol, n-propanol, isopropanol, tertbutanol, etc.), ketones (e.g., acetone, methyl ethyl ketone, etc.), cyclic ethers (e.g., tetrahydrofuran, dioxane, etc.), esters (e.g., ethyl acetate, etc.), chlorinated hydrocarbons (e.g., methylene chloride, chloroform, etc.), amides (e.g., dimethylformamide, dimethylacetamide, etc.), sulfoxides (e.g., dimethyl sulfoxide, etc.), nitriles (e.g., acet
  • the organic solvent used for dissolving the oleophilic polymer coupler is removed from the mixture before coating the dispersed solution or at vaporization during drying of the coated dispersed solution, although the latter is rather unpreferable.
  • a method in which the solvent is removed by washing a gelatin noodle with water is applied when the solvent is water-soluble to some extent or a spray drying method, a vacuum purging method or a steam purging method can be employed for removing the solvent.
  • removable organic solvents examples include esters (such as lower alkyl esters), lower alkyl ethers, ketones, halogenated hydrocarbons (e.g., methylene chloride, trichloroethylene or hydrocarbon fluoride), alcohols (e.g., alcohols between n-butyl alcohol and octyl alcohol), and combinations thereof.
  • esters such as lower alkyl esters
  • lower alkyl ethers such as ketones
  • halogenated hydrocarbons e.g., methylene chloride, trichloroethylene or hydrocarbon fluoride
  • alcohols e.g., alcohols between n-butyl alcohol and octyl alcohol
  • any type agents may be used, but an ionic surfactant, in particular, anionic type surfactant, is suitable.
  • the amphoteric type surfactant such as N-alkylaminopropionic acid salts and N-alkyliminodipropionic acid salts may be also used.
  • a permanent solvent i.e., a water non-miscible organic solvent having a high boiling point (200° C. or more), may be added.
  • the concentration of the permanent solvent is preferably low.
  • the ratio of the color forming portion corresponding to the general formula (I) in the oleophilic polymer coupler is usually from 5 to 80% by weight. Particularly, a ratio from 20 to 70% by weight is preferred in view of color reproducibility, color forming property and stability.
  • an equivalent molecular weight that is, a gram number of the polymer containing 1 mol of the monomeric coupler, is preferably from about 250 to 4,000, but it is not limited thereto.
  • the average molecular weight was measured by the gel permeation chromatography (GPC) under the following conditions.
  • TSK gel (a trade mark for cross-linked polystyrene, made by Toyo Soda Manufacturing Co., Ltd.);
  • G2000H8 1 unit; (Molecular weight of exclusion limit: 10,000); (Column dimensions: 7.51 mm(D) ⁇ 600 mm(L))
  • G4000H8 1 unit; (Molecular weight of exclusion unit: 400,000); (Column dimensions: 7.51 mm(D) ⁇ 600 mm(L))
  • UV-8 Model II made by Toyo Soda Manufacturing Co., Ltd.
  • a calibration curve was prepared by using TSK standard polystyrene.
  • Copolymer coupler composed of 1-(2,4,6-trichlorophenyl)-3-methacrylamido-2-pyrazolin-5-one (C-1) and butyl acrylate:
  • this copolymer contains 52.0% of monomeric coupler (C-1). GPC gave a number average molecular weight of 105,000.
  • Copolymer coupler composed of 1-(2,4,6-trichlorophenyl)-3-methacrylamido-2-pyrazolin-5-one (C-1) and butyl acrylate:
  • Copolymer coupler composed of 1-(2,4,6-trichlorophenyl)-3-methacrylamido-2-pyrazolin-5-one (C-1) and butyl acrylate.
  • the effect of this invention is to overcome the disadvantage of the conventional magenta coupler by using certain magenta couplers having high molecular weight.
  • the nucleus is a nitrogen-containing heterocyclic ring, and this heterocyclic ring tends to be adsorbed to the surface of silver halide. This adsorption delays the development of silver halide, and hence lowers the sensitivity.
  • the polymer coupler according to the present invention having a high molecular weight is inhibited to be adsorbed to silver halide, and thus the silver halide exhibits its inherent sensitivity.
  • the polymer coupler should have a number average molecular weight higher than 30,000.
  • a conventional polymer coupler having a number average molecular weight of about 10,000 still has a tendency to lower the sensitivity of emulsion.
  • the photographic light-sensitive material produced according to this invention may contain a conventional magenta coupler of low molecular weight in addition to the magenta polymer coupler.
  • magenta couplers include 5-pyrazolone coupler, pyrazolobenzimidazole coupler, cyanoacetylcoumarone coupler, and open chain acylacetonitrile coupler.
  • the photographic light-sensitive material produced according to this invention may contain a yellow coupler and a cyan coupler in addition to the magenta coupler.
  • the yellow coupler includes acylacetamide coupler (e.g., benzoylacetanilide and pivaloylacetanilide).
  • the cyan coupler includes naphthol coupler and phenol coupler. These couplers should preferably be of a nondiffusible type which has a hydrophobic group, also preferred to as a ballast group, in the molecule
  • the coupler may be 4-equivalent or 2-equivalent with respect to the silver ion.
  • the coupler may be one which has a color correction effect or one which releases the development inhibitor as development proceeds (i.e., a so-called DIR coupler).
  • the photographic light-sensitive material of this invention may contain, in addition to a DIR coupler, a non-color developing DIR coupling compound which forms a colorless coupling reaction product and releases a development inhibitor.
  • the photographic emulsion used in this invention may be produced by the processes described in Chimie et Physique Photographique, by P. Glafkides (published by Paul Montel, 1967), Photographic Emulsion Chemistry, by G. F. Duffin (published by The Focal Press, 1966), and Making and Coating Photographic Emulsions, by V. L. Zelikman et al. (published by The Focal Press, 1964). In other words, it may be produced by acidic process, neutral process, or ammoniacal process.
  • the reaction of soluble silver salt and soluble halogen salt may be accomplished by a single jet method, a double jet method, or a combination thereof. According to another process (so-called reverse mixing), the grains are formed in the presence of excess silver ions.
  • the formation or physical ripening of silver halide grains may be accomplished in the presence of a cadmium salt, a zinc salt, a lead salt, a thallium salt, an iridium salt or a complex thereof, a rhodium salt or a complex thereof, or an iron salt or a complex thereof.
  • the silver halide grains in the photographic emulsion may be regular crystals such as cubic and octahedral, or irregular crystals such as spherical and tabular (having a length/thickness ratio greater than 5, or even greater than 8), or crystals of complex forms. A mixture of grains of various crystal forms is also acceptable.
  • the silver halide grains may be composed of the internal layer and external layer which are different from each other, or may be composed of a uniform phase. They may be such that the latent image is formed mainly on the surface thereof, or may be such that the latent image is formed mainly inside the grain.
  • the light-sensitive material of this invention may contain a color antifoggant such as a hydroquinone derivative, an aminophenol derivative, a gallic acid derivative, and an ascorbic acid derivative.
  • a color antifoggant such as a hydroquinone derivative, an aminophenol derivative, a gallic acid derivative, and an ascorbic acid derivative.
  • the light-sensitive material of this invention may contain in the hydrophilic colloid layer a water-soluble dye as a filter dye, or for the prevention of irradiation and other purposes.
  • a water-soluble dye as a filter dye, or for the prevention of irradiation and other purposes.
  • a water-soluble dye examples include an oxonol dye, a hemioxonol dye, a stryryl dye, a merocyanine dye, a cyanine dye, and an azo dye.
  • an oxonol dye, a hemioxonol dye, and a merocyanine dye are useful among them.
  • the photographic emulsion of this invention may be incorporated with various compounds in order to prevent the photographic fog that might occur in the production or preservation of the light-sensitive material or in the photographic processing, or in order to stabilize the photographic performance.
  • these compounds include known antifoggants and stabilizers, for example, azoles such as benzothiazolium salts, nitroindazoles, triazoles, benzotriazoles, and benzimidazoles (particularly nitro- or halogen-substituted ones); heterocyclic mercapto compounds such as mercaptothiazoles, mercaptobenzothiazoles, mercaptobenzimidazoles, mercaptothiadiazoles, mercaptotetrazoles (particularly 2-phenyl-5-mercaptotetrazole), and mercaptopyrimidines; those among the above-mentioned heterocyclic mercapto compounds which have a water-soluble group such as a carboxyl group and a sulfone group;
  • the photographic emulsion layer of the light-sensitive material of this invention may contain, for the purpose of sensitivity increase, contrast increase, and development acceleration, polyalkylene oxides or derivatives thereof such as ethers, esters, and amines, thioether compounds, thiomorpholines, quaternary ammonium salts, urethane derivatives, urea derivatives, imidazole derivatives, and 3-pyrazolidones.
  • polyalkylene oxides or derivatives thereof such as ethers, esters, and amines, thioether compounds, thiomorpholines, quaternary ammonium salts, urethane derivatives, urea derivatives, imidazole derivatives, and 3-pyrazolidones.
  • Sample A of multilayered film was prepared by coating emulsion layers and auxiliary layers, in the order mentioned below, on a triacetyl cellulose support.
  • the 1st layer Slow-speed red sensitive emulsion layer
  • An emulsion was prepared by dissolving 100 g of a cyan coupler (2-(heptafluorobutylamide)-5-[2'-(2",4"-di-t-aminophenoxy)butylamide]-phenol) in 100 cc of tricresyl phosphate and 100 cc of ethyl acetate, and mixing with high speed agitation the resulting solution with 1 kg of 10% aqueous solution of gelatin.
  • a cyan coupler (2-(heptafluorobutylamide)-5-[2'-(2",4"-di-t-aminophenoxy)butylamide]-phenol
  • 500 g of the emulsion was mixed with 1 kg of slow-speed red sensitive silver iodobromide emulsion (containing 70 g of silver and 60 g of gelatin and 6 mol % of iodine; having a grain size distribution such that 81% of the total number of silver halide grains falls under ⁇ 40% of the average grain size).
  • the resulting emulsion was applied to the support so that the dry layer thereof was 2 ⁇ m thick (silver quantity: 0.5 g/m 2 ).
  • the 2nd layer Medium-speed red sensitive layer
  • An emulsion was prepared by dissolving 100 g of a cyan coupler (2-(heptafluorobutylamide)-5-[2'-(2",4"-di-t-aminophenoxy)butylamide]-phenol) in 100 cc of tricresyl phosphate and 100 cc of ethyl acetate, and mixing with high speed agitation the resulting solution with 1 kg of 10% aqueous solution of gelatin.
  • a cyan coupler (2-(heptafluorobutylamide)-5-[2'-(2",4"-di-t-aminophenoxy)butylamide]-phenol
  • the emulsion 1000 g was mixed with 1 kg of medium-speed red sensitive silver iodobromide emulsion (containing 70 g of silver and 60 g of gelatin and 6 mol % of iodine; having a grain size distribution of 76% measured as mentioned above for the 1st layer).
  • the resulting emulsion was applied so that the dry layer thereof was 1 ⁇ m thick (silver quantity: 0.4 g/m 2 )
  • the 3rd layer High-speed red sensitive layer
  • An emulsion was prepared by dissolving 100 g of a cyan coupler (2-(heptafluorobutylamide)-5-[2'-(2",4"-di-t-aminophenoxy)butylamide]-phenol) in 100 cc of tricresyl phosphate and 100 cc of ethyl acetate, and mixing with high speed agitation the resulting solution with 1 kg of 10% aqueous solution of gelatin.
  • a cyan coupler (2-(heptafluorobutylamide)-5-[2'-(2",4"-di-t-aminophenoxy)butylamide]-phenol
  • the 4th layer Interlayer
  • An emulsion was prepared by dissolving 2,5-di-t-octylhydroquinone in 100 cc of dibutyl phthalate and 100 cc of ethyl acetate, and mixing with high speed agitation the resulting solution with 1 kg of 10% aqueous solution of gelatin. 1 kg of the emulsion was mixed with 1 kg of 10% aqueous solution of gelatin. The resulting emulsion was applied so that the dry layer thereof was 1 ⁇ m thick.
  • the 5th layer Slow-speed green sensitive emulsion layer
  • An emulsion was prepared in the same way as for the 1st layer, except that the cyan coupler was replaced by a magenta coupler (1-(2,4,6-trichlorophenyl)-3-[3-(2,4-di-t-amylphenoxyacetamide)benzamide]-5-pyrazolone).
  • 500 g of the emulsion was mixed with 1 kg of slow-speed green sensitive silver iodobromide emulsion (containing 70 g of silver and 60 g of gelatin and 5.2 mol % of iodine; having a grain size distribution of 81% measured as mentioned above).
  • the resulting emulsion was applied so that the dry layer thereof was 2.0 ⁇ m thick (silver quantity: 0.7 g/m 2 )
  • the 6th layer Medium-speed green sensitive emulsion layer
  • An emulsion was prepared in the same way as for the 1st layer, except that the cyan coupler was replaced by a magenta coupler (1-(2,4,6-trichlorophenyl)-3-[3-(2,4-di-t-amylphenoxyacetamide)behzamide]-5-pyrazolone).
  • 1000 g of the emulsion was mixed with 1 kg of high-speed green sensitive silver iodobromide emulsion (containing 70 g of silver and 60 g of gelatin and 5.2 mol % of iodine; having a grain size distribution of 75% measured as mentioned above).
  • the resulting emulsion was applied so that the dry layer thereof was 1 ⁇ m thick (silver quantity: 0.35 g/m 2 ).
  • the 7th layer High-speed green sensitive emulsion layer
  • An emulsion was prepared in the same way as for the 1st layer, except that the cyan coupler was replaced by a magenta coupler (1-(2,4,6-trichlorophenyl)-3-[3-(2,4-di-t-amylphenoxyacetamide)benzamide]-5-pyrazolone).
  • 1000 g of the emulsion was mixed with 1 kg of high-speed green sensitive silver iodobromide emulsion (containing 70 g of silver and 60 g of gelatin and 5.2 mol % of iodine; having a grain size distribution of 75% measured as mentioned above).
  • the resulting emulsion was applied so that the dry layer thereof was 1 ⁇ m thick (silver quantity: 0.35 g/m 2 ).
  • the 8th layer Interlayer
  • the 9th layer Yellow filter layer
  • An emulsion containing yellow colloidal silver was applied so that the dry layer thereof was 1 ⁇ m thick.
  • the 10th layer Slow-speed blue sensitive emulsion layer
  • An emulsion was prepared in the same way as for the 1st layer, except that the cyan coupler was replaced by a yellow coupler ( ⁇ -(pivaloyl)- ⁇ -(1-benzyl-5-ethoxy-3-hydantoinyl)-2-chloro-5-dodecyloxycarbonyl-acetanilide).
  • 1000 g of the emulsion was mixed with 1 kg of slow-speed blue sensitive silver iodobromide emulsion (containing 70 g of silver and 60 g of gelatin and 5.5 mol % of iodine; having a grain size distribution of 77% measured as mentioned above).
  • the resulting emulsion was applied so that the dry layer thereof was 2.0 ⁇ m thick (silver quantity: 0.6 g/m 2 ).
  • the 11th layer Medium-speed blue sensitive emulsion layer
  • An emulsion was prepared in the same way as for the lst layer, except that the cyan coupler was replaced by a yellow coupler ( ⁇ -(pivaloyl)- ⁇ -(1-benzyl-5-ethoxy-3-hydantoinyl)-2-chloro-5-dodecyloxycarbonyl-acetanilide).
  • 1000 g of the emulsion was mixed with 1 kg of high-speed blue sensitive silver iodobromide emulsion (containing 70 g of silver and 60 g of gelatin and 5.5 mol % of iodine; having a grain size distribution of 72% measured as mentioned above).
  • the resulting emulsion was applied so that the dry layer thereof was 1.0 ⁇ m thick (silver quantity: 0.5 g/m 2 ).
  • the 12th layer High-speed blue sensitive emulsion layer
  • An emulsion was prepared in the same way as for the 1st layer, except that the cyan coupler was replaced by a yellow coupler ( ⁇ -(pivaloyl)- ⁇ -(1-benzyl-5-ethoxy-3- hydantoinyl)-2-chloro-5-dodecyloxycarbonyl-acetanilide).
  • 1000 g of the emulsion was mixed with 1 kg of high-speed blue sensitive silver iodobromide emulsion (containing 70 g of silver and 60 g of gelatin and 5.5 mol % of iodine; having a grain size distribution of 72% measured as mentioned above).
  • the resulting emulsion was applied so that the dry layer was 1.0 ⁇ m thick (silver quantity: 0.5 g/m 2 ).
  • the 13th layer The second protective layer
  • the 14th layer The first protective layer
  • a 10% gelatin aqueous solution containing an emulsion of fine grains (grain size: 0.15 ⁇ m, 1 mol % silver iodobromide) which is not chemically sensitized was applied so that the dry layer thereof was 1 ⁇ m thick (silver quantity: 0.3 g/m 2 ).
  • polymer coupler latexes (a), (b), (c), (d), and (e) were prepared from polymer coupler (A) (for comparison), and polymer couplers (II), (I), (III), and (X) of this invention, respectively, in the following way.
  • Each polymer coupler (20 g in the case of polymer coupler (A) for comparison, and an equimolar amount to the 20 g of polymer coupler (A) in the case of polymer couplers of this invention in terms of color forming unit moiety) was dissolved with heating in 60 ml of ethyl acetate, and the resulting solution was added to 300 ml of aqueous solution containing 15 g of gelatin and 1.2 g of sodium laurylsulfate, followed by dispersion by a colloid mill. Finally, the ethyl acetate was removed under reduced pressure.
  • samples B, C, D, E, and F were prepared, respectively, in the same way as for sample A.
  • Each latex was used in an equimolar amount of the magenta coupler in terms of coupler unit.
  • the samples A to F were exposed to light and underwent the reversal color process.
  • the first development was performed for 6 minutes for standard processing; and in the second experiment, the first development was performed for 10 minutes for sensitization processing.
  • Sample (1) of multilayered color light-sensitive material was prepared by forming the following layers on a polyethylene terephthalate film support.
  • the 1st layer Antihalation layer
  • a gelatin layer containing black colloidal silver is provided.
  • the 2nd layer Interlayer
  • the 3rd layer Slow-sensitive red sensitive emulsion layer
  • the 4th layer High-speed red sensitive emulsion layer
  • the 5th layer Interlayer
  • the 6th layer Slow-speed green sensitive emulsion layer
  • the 7th layer High-speed green sensitive emulsion layer
  • the 8th layer Yellow filter layer
  • the 9th layer Slow-speed blue sensitive emulsion layer
  • the 10th layer High-speed blue sensitive emulsion layer Silver iodobromide emulsion
  • the 11th layer The first protective layer
  • a gelatin layer of an emulsion containing silver iodobromide (silver iodide: 1 mol %, average grain size: 0.07 ⁇ m, silver quantity: 0.5 g/m 2 ) and ultravilot absorber UV-1.
  • the 12th layer The second protective layer
  • a gelatin layer containing polymethyl methacrylate grains (about 1.5 ⁇ m in diameter).
  • gelatin hardener H-1 and surface active agent were added to each layer.
  • polymer coupler latexes (a), (b), (c), (d), and (e) were prepared from polymer couple (A) (for comparison), and polymer couplers (II), (I), (III), and (X) of this invention, respectively, in the following way.
  • Each polymer coupler (20 g in the case of polymer coupler (A) for comparison, and an equimolar amount to the 20 g of polymer coupler (A) in the case of polymer coupler of this invention in terms of color forming unit moiety) was dissolved with heating in 60 ml of ethyl acetate, and the resulting solution was added to 300 ml of aqueous solution containing 15 g of gelatin and 1.2 g of sodium laurylsulfate, followed by dispersion by a colloid mill. Finally, the ethyl acetate was removed under reduced pressure.
  • samples (2), (3), (4), (5), and (6) were prepared, respectively, in an analogous manner as for sample (1).
  • Each latex was used in an equimolar amount of the magenta coupler of sample (1) in terms of coupler unit.
  • the samples (1) to (6) were exposed to light and underwent the color negative process.
  • the color development was performed for 3 minutes and 15 seconds for standard processing; and in the second experiment, the color development was performed for 6 minutes and 20 seconds for sensitization processing.
  • the development was performed as follows at 38° C.
  • composition of the processing solution used for the processing solution used for the processing solution.
  • the coupler couplers, gelatin hardener, ultraviolet absorber, and sensitizing dyes used are as follows. ##STR5##
  • polymer coupler (B) The resulting polymer is hereinafter referred to as "polymer coupler (B)".
  • GPC gave a number average molecular weight of 12,500.
  • Test samples were prepared in the same manner as in Example 1. After development, the sensitivity of the magenta image was measured, and the difference ( ⁇ S) between the sensitivity (*1) in sensitization processing and the sensitivity in standard processing was obtained. The results are shown in the following Table 4.
  • Test samples were prepared in the same manner as in Example 1. After development, the sensitivity of the magenta image was measured, and the difference ( ⁇ S) between the sensitivity (*1) in sensitization processing and the sensitivity in standard processing was obtained. The results are shown in the following Table 5.

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  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Silver Salt Photography Or Processing Solution Therefor (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
US06/783,505 1983-07-20 1985-10-03 Silver halide color light-sensitive material Abandoned USH156H (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP58132135A JPS6023856A (ja) 1983-07-20 1983-07-20 ハロゲン化銀カラ−感光材料
JP58-132135 1983-07-20

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US (1) USH156H (de)
EP (1) EP0133262A3 (de)
JP (1) JPS6023856A (de)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6365334B1 (en) * 1993-10-22 2002-04-02 Eastman Kodak Company Photographic elements containing aryloxypyrazolone couplers and sulfur containing stabilizers
US20100063654A1 (en) * 2008-09-08 2010-03-11 L-3 Communications Corporation Locator Beacon Disposed Internal to an Enclosure of a Flight Data Recorder and Method Therefor

Families Citing this family (9)

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JPS6050534A (ja) * 1983-08-30 1985-03-20 Konishiroku Photo Ind Co Ltd ハロゲン化銀カラ−写真感光材料
JPH03135549A (ja) * 1984-04-17 1991-06-10 Konica Corp ハロゲン化銀カラー写真感光材料
JPH0642059B2 (ja) * 1984-04-17 1994-06-01 コニカ株式会社 ハロゲン化銀カラ−写真感光材料
JPH03135550A (ja) * 1984-04-17 1991-06-10 Konica Corp ハロゲン化銀カラー写真感光材料
JPS6142652A (ja) * 1984-08-07 1986-03-01 Fuji Photo Film Co Ltd ハロゲン化銀写真感光材料
JPH0812388B2 (ja) * 1985-04-22 1996-02-07 コニカ株式会社 ハロゲン化銀カラー写真感光材料
US4745048A (en) * 1985-06-07 1988-05-17 Fuji Photo Film Co., Ltd. Silver halide color photographic material and method of processing the same using an improved desilvering accelerator
DE3873942T2 (de) * 1987-03-20 1993-07-01 Fuji Photo Film Co Ltd Silberhalogenidhaltiges photographisches farbmaterial.
EP0583832A1 (de) * 1992-08-19 1994-02-23 Eastman Kodak Company Farbphotographische Materialien, die 5-Pyrazolon-Polymerkuppler und Lösungsmittel enthalten

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US4409320A (en) 1981-05-08 1983-10-11 Fuji Photo Film Co., Ltd. Silver halide color photographic light-sensitive material
US4411987A (en) 1981-11-06 1983-10-25 Fuji Photo Film Co., Ltd. Silver halide color photographic light-sensitive material
US4435503A (en) 1981-07-13 1984-03-06 Fuji Photo Film Co., Ltd. Silver halide color photographic light-sensitive material
US4436808A (en) 1982-02-25 1984-03-13 Fuji Photo Film Co., Ltd. Silver halide color photographic light-sensitive material
US4474870A (en) 1982-01-11 1984-10-02 Fuji Photo Film Company Limited Silver halide color photographic light-sensitive material
US4540654A (en) 1983-03-18 1985-09-10 Fuji Photo Film Co., Ltd. Method of forming color image comprising heterocyclic magenta dye-forming coupler

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US3163625A (en) * 1960-04-13 1964-12-29 Du Pont Color-forming monomers and polymers of acrylic acid amides of 3-aminopyrazolone
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US4409320A (en) 1981-05-08 1983-10-11 Fuji Photo Film Co., Ltd. Silver halide color photographic light-sensitive material
US4435503A (en) 1981-07-13 1984-03-06 Fuji Photo Film Co., Ltd. Silver halide color photographic light-sensitive material
US4411987A (en) 1981-11-06 1983-10-25 Fuji Photo Film Co., Ltd. Silver halide color photographic light-sensitive material
US4474870A (en) 1982-01-11 1984-10-02 Fuji Photo Film Company Limited Silver halide color photographic light-sensitive material
US4436808A (en) 1982-02-25 1984-03-13 Fuji Photo Film Co., Ltd. Silver halide color photographic light-sensitive material
US4540654A (en) 1983-03-18 1985-09-10 Fuji Photo Film Co., Ltd. Method of forming color image comprising heterocyclic magenta dye-forming coupler

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6365334B1 (en) * 1993-10-22 2002-04-02 Eastman Kodak Company Photographic elements containing aryloxypyrazolone couplers and sulfur containing stabilizers
US20100063654A1 (en) * 2008-09-08 2010-03-11 L-3 Communications Corporation Locator Beacon Disposed Internal to an Enclosure of a Flight Data Recorder and Method Therefor

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Publication number Publication date
EP0133262A3 (en) 1985-12-11
JPS6023856A (ja) 1985-02-06
EP0133262A2 (de) 1985-02-20

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