EP0412379B1 - Matériaux photographiques couleur à l'halogénure d'argent sensibles à la lumière - Google Patents

Matériaux photographiques couleur à l'halogénure d'argent sensibles à la lumière Download PDF

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EP0412379B1
EP0412379B1 EP90114522A EP90114522A EP0412379B1 EP 0412379 B1 EP0412379 B1 EP 0412379B1 EP 90114522 A EP90114522 A EP 90114522A EP 90114522 A EP90114522 A EP 90114522A EP 0412379 B1 EP0412379 B1 EP 0412379B1
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Prior art keywords
group
layer
dye
formula
silver halide
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German (de)
English (en)
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EP0412379A1 (fr
Inventor
Toru Harada
Toshiyuki Watanabe
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Fujifilm Holdings Corp
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Fuji Photo Film Co Ltd
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Priority claimed from JP20931489A external-priority patent/JPH0372340A/ja
Priority claimed from JP20931589A external-priority patent/JPH0372342A/ja
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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
    • G03C1/00—Photosensitive materials
    • G03C1/005—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein
    • G03C1/06—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein with non-macromolecular additives
    • G03C1/08—Sensitivity-increasing substances
    • G03C1/10—Organic substances
    • G03C1/12—Methine and polymethine dyes
    • 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
    • G03C1/00—Photosensitive materials
    • G03C1/76—Photosensitive materials characterised by the base or auxiliary layers
    • G03C1/825—Photosensitive materials characterised by the base or auxiliary layers characterised by antireflection means or visible-light filtering means, e.g. antihalation
    • G03C1/83—Organic dyestuffs therefor
    • G03C1/832—Methine or polymethine dyes

Definitions

  • This invention relates to silver halide color photographic light-sensitive materials which have a novel dye containing layer.
  • the dyes which are used for such purposes must satisfy various conditions. For example, they must have absorption spectral characteristics which are satisfactory for the intended use, they must have no adverse effects, such as fogging or desensitization on the photographic emulsion, they must not diffuse from the colored layer into other layers and they must have excellent storage stability and aging stability and remain unchanged in solution or in the silver halide color photographic light-sensitive material.
  • the layer which contains the above mentioned dyes functions as a filter layer or an anti-halation layer
  • An object of the present invention is to provide silver halide color photographic light-sensitive materials in which there is a dye layer which is stable in long term storage and which does not adversely affect photographic performance.
  • a second object of the present invention is to provide silver halide color photographic light-sensitive materials in which there is a filter effect, an anti-halation effect or sensitivity controlling effect of a light-sensitive emulsion.
  • a third object of the present invention is to provide silver halide color photographic light-sensitive materials which have excellent color reproduction properties.
  • a fourth object of the present invention is to obtain silver halide color photographic light-sensitive materials in which there are dyed layers in which specific layers are selectively dyed and the color is not spread into other layer.
  • R7 represents an alkyl group
  • R8 and R9 may be the same or different, each representing an alkyl group, and a five or six membered ring may be formed by R8 and R9
  • R10 represents a hydrogen atom, a halogen atom , an alkyl group, an alkoxy group, a hydroxyl group, an amino group, a carbamoyl group, a sulfamoyl group or an alkoxycarbonyl group; with the proviso that at least one of the groups R7, R8, R9 and R10 contains an alkyl chain which has at least four carbon atoms.
  • X and Y may be the same or different, each representing a cyano group, a carboxyl group, an alkylcarbonyl group, an arylcarbonyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, a carbamoyl group, a sulfonyl group or a sulfamoyl group. Furthermore, cases in which the combination of X and Y is (cyano group, arylcarbonyl group), (cyan group, alkylcarbonyl group) or (cyano group, sulfonyl group) are excluded.
  • R3 and R4 may be the same or different, each representing a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, a hydroxy group, a carboxyl group, an amino group, a carbamoyl group, a sulfamoyl group or an alkoxycarbonyl group.
  • R5 and R6 may be the same or different, each representing a hydrogen atom, an alkyl group or an aryl group, and R5 and R6 may form a five or six membered ring.
  • R3 and R5, or R4 and R6, may be joined together and form a five or six membered ring.
  • the substituent groups described above may be further substituted with other substituent groups.
  • the aryl groups represented by R5 and R6, and the aryl moieties of the arylcarbonyl groups represented by X and Y and of the aryloxycarbonyl groups represented by X and Y are preferably phenyl groups or naphthyl groups. Furthermore, these may be substituted with alkyl groups (as described earlier), alkoxy groups (described hereinafter), halogen atoms, nitro groups, cyano groups, hydroxy groups, carboxyl groups, carbamoyl groups (described hereinafter) sulfo groups, sulfamoyl groups (described hereinafter), alkoxycarbonyl groups (described hereinafter) or amino groups, for example.
  • alkyl moieties of the alkoxy groups represented by R3 and R4 and of the alkoxycarbonyl groups represented by R3, R4, X and Y have the same meaning as those described earlier.
  • the carbamoyl groups represented by R3, R4, X and Y and the sulfamoyl groups represented by R3, R4, X and Y may be substituted with the aforementioned alkyl groups and aryl groups, for example.
  • the sulfonyl groups represented by X and Y may be substituted with the aforementioned alkyl groups and aryl groups, for example.
  • the amino groups represented by R3 and R4 may be substituted with alkyl groups (as described earlier), aryl groups (as described earlier), COR' or SO2R' (where R' is an alkyl group or an aryl group as described earlier), for example.
  • Fluorine, chlorine, bromine and iodine are cited as halogen atoms which can be represented by R3 and R4.
  • a five or six membered heterocyclic ring (for example, a piperidine ring or a morpholine ring) may be formed by R5 and R6.
  • R3 and R5, or R4 and R6, may be joined together to form a five or six membered ring.
  • n 0 or 1
  • m represents 1 to 5.
  • the dyes represented by formula (2) can be more preferably represented by formula (4) indicated below.
  • the dyes of formula (3) are most desirably dyes in which the alkyl group of R7 is branched.
  • X represents an alkylcarbonyl group (as described earlier) or an arylcarbonyl group (as described earlier).
  • R3 to R6 have the same meaning as described earlier.
  • Compounds 1 to 23 are indicated by showing the actual groups represented by R7, R8, R9 and R10 in formula (3).
  • the dye compounds used in the present invention can be prepared easily in the following way. Typical examples are cited below, but other compounds can be prepared in the same way. Refer to A. Weissberger, The Chemistry of Heterocyclic Compound , Vol. 7, pages 117 to 140 in connection with the synthesis of 5-isoxazolones.
  • the dyes of formula (3) and/or formula (2) are used in amounts of from 1 to 800 mg per square meter of light-sensitive material.
  • the dyes represented by formula (3) and/or formula (2) are used as filter dyes, anti-halation dyes or color correcting dyes, they can be used in any amount which is effective, but they are preferably used in such a way that the optical density is within the range from 0.05 to 3.0.
  • the addition may be made at any stage prior to coating.
  • the dyes of formula (3) can be more preferably used as anti-halation dyes or color correcting dyes. When the dyes are used for these purposes, they can be used in amounts of from 0.01 to 0.7 g, more preferably from 0.01 to 0.2 g, per square meter of light-sensitive material.
  • the dyes of formula (2) or formula (4) can be more preferably used as filter dyes. When the dyes are used for the purpose, they can be used in amounts of from 0.01 to 0.7 g, preferably 0.02 to 0.2 g, per square meter of light-sensitive material.
  • the dyes of the present invention can be dispersed using a variety of known methods in emulsion layers or other hydrophilic colloid layers (for example, intermediate layers, protective layers, anti-halation layers and filter layers).
  • the dyes of formula (2) or formula (4) can be more preferably added in a light-insensitive emulsion layer or layers provided further than a green-sensitive emulsion layer from the support.
  • the dyes of formula (3) can be more preferably added in a light-insensitive emulsion layer or layers provided between the support and a red-sensitive emulsion layer.
  • the mol ratio of the dye of formula (3) to the dye of formula (2) is preferably not more than 1.
  • hydrosols of oleophilic polymers as disclosed in JP-B-51-39835 for example can also be added to the hydrophilic colloidal dispersions obtained in the ways described above.
  • Gelatin is a typical hydrophilic colloid, but any of the other known hydrophilic colloids which are used for photographic purposes can be used.
  • Silver bromide, silver iodobromide, silver iodochlorobromide, silver chlorobromide or silver chloride can be used for the silver halide emulsion which is used in the present invention.
  • the use of silver bromide, silver chlorobromide, silver iodobromide or silver iodochlorobromide is preferred.
  • the silver halide grains in the photographic emulsion layer may have a regular crystalline form, such asa cubic or octahedral form, an irregular crystalline form, such as a spherical or tabular form, or a crystalline form which is a composite of these crystalline forms. Use can also be made of mixtures of grains which have various crystalline forms.
  • the silver halide grains may be such that the interior and surface layer consist of different phases or they may be comprised of a uniform phase. Furthermore, the silver halide grains may be of the type with which the latent image is formed principally on the surface of the grains (for example, a negative type emulsion) or they may be of the type with which the latent image is formed principally within the grains (for example, internal latent image type emulsions and pre-fogged direct reversal type emulsions).
  • the silver halide emulsions used in the present invention may be such that tabular grains of thickness not more than 0.5 microns, and preferably not more than 0.3 microns, and of diameter preferably at least 0.6 microns and of which the average aspect ratio is at least 5 account for at least 50% of the total projected area. Furthermore, they may be monodisperse emulsions such that grains of grain size within the average grain size ⁇ 40% account for at least 95% by number of all of the grains.
  • the photographic emulsions used in the present invention can be prepared, for example, using the methods disclosed in P. Glafkides, Chimie et Physique Photographique , published by Paul Montel, (1966), in G.F. Duffin, Photographic Emulsion Chemistry , published by Focal Press, (1966), and in V.L. Zelikmann et al., Making and Coating Photographic Emulsion , published by Focal Press, (1964).
  • silver halide solvents for example, ammonia, potassium thiocyanate, ammonium thiocyanate, thioether compounds (for example, those disclosed in U.S. Patents 3,271,157, 3,574,628, 3,704,130, 4,297,439 and 4,276,374), thione compounds (for example, those disclosed in U.S. Patent 4,284,717, JP-A-53-144319 and JP-A-53-82408), and amine compounds (for example, those disclosed in JP-A-54-100717) can be used to control grain growth during the formation of the silver halide grains.
  • ammonia, potassium thiocyanate, ammonium thiocyanate, thioether compounds for example, those disclosed in U.S. Patents 3,271,157, 3,574,628, 3,704,130, 4,297,439 and 4,276,374
  • thione compounds for example, those disclosed in U.S. Patent 4,284,717, JP-A-53-144319
  • Cadmium salts, zinc salts, thallium salts, iridium salts or complex salts thereof, rhodium salts or complex salts thereof, and iron salts or complex salts thereof, for example, may be present during the formation or physical ripening of the silver halide grains.
  • the silver halide emulsions are normally subjected to chemical sensitization.
  • the methods described, for example, in H. Frieser, Die Unen der Photographischen Too mit Silberhalogeniden, pages 675 to 734, published by Akademische Verlagsgeseleschaft, (1968) can be used for this purpose.
  • Sulfur sensitization methods using active gelatin or compounds which contain sulfur which can react with silver for example, thiosulfate, thioureas, mercapto compounds, rhodanines
  • reduction sensitization methods using reducing substances for example, stannous salts, amines, hydrazine derivatives, formamidinesulfinic acids, silane compounds
  • noble metal sensitization methods using noble metal compounds for example, complex salts of the metals of group VIII of the periodic table, such as Pt, Ir or Pd, as well as gold
  • Various compounds can be included in the emulsions used in the present invention with a view to preventing the occurrence of fogging during the manufacturing, storage or photographic processing of the light-sensitive materials or with a view to stabilizing photographic performance.
  • many compounds can be employed which are known as anti-foggants or stabilizers, such as azoles, for example, benzothiazolium salts, nitroindazoles, triazoles, benzotriazoles and benzimidazoles (especially nitro or halogen substituted derivatives); heterocyclic mercapto compounds, for example, mercaptothiazoles, mercaptobenzothiazoles, mercaptobenzimidazoles, mercaptothiadiazoles, mercaptotetrazoles (especially 1-phenyl-5-mercaptotetrazole) and mercaptopyrimidines; heterocyclic mercapto compounds as described above but which have water solubilizing groups such as carboxyl groups and sulfo groups;
  • Ultraviolet absorbers such as benzothiazoles may be used jointly in the light-sensitive materials of the present invention, and typical examples have been disclosed, for example, in Research Disclosure, No. 24239 (June, 1984).
  • Color couplers such as cyan couplers, magenta couplers and yellow couplers can be included in the silver halide photographic emulsions used in the present invention.
  • compounds which can form colors by oxidative coupling with the primary aromatic amine developing agents for example, phenylenediamine derivatives and aminophenol derivatives
  • the primary aromatic amine developing agents for example, phenylenediamine derivatives and aminophenol derivatives
  • Patent 3,725,067 or the pyrazolo[5,1-b][1,2,4]triazoles disclosed in European Patent 119,860 can be used as magenta couplers, and acylacetamide couplers (for example, benzoylacetanilides and pivaloylacetanilides), for example, can be used as yellow couplers and naphthol couplers and phenol couplers, for example, can be used as cyan couplers, but couplers which are fast to humidity and temperature are preferably used, and typical examples include the phenol based couplers disclosed, for example, in U.S. patent 3,772,002, the 2,5-diacylaminophenol based couplers disclosed, for example, in U.S.
  • Patent 4,463,086, JP-A-59-166956 and JP-A-58-133293 the phenol based couplers which have a phenylureido group in the 2-position and an acylamino group in the 5-position disclosed, for example, in U.S. Patent 4,333,999, and moreover the 5-position substituted naphthol based couplers and polymer couplers thereof disclosed in JP-A-60-237448, and Japanese Patent Application Nos. 59-264277 and 59-268135 (coresponding to JP-A-61-153640 and JP-A-61-145557, respectively).
  • These couplers are preferably fast to difusion, having hydrophobic groups, known as ballast groups, within the molecule.
  • the couplers may be of the four equivalent type or two equivalent type with respect to silver ion. Furthermore, colored couplers which have a color correcting effect and couplers which release development inhibitors during the course of development (so-called DIR couplers) can also be used.
  • colorless compound forming DIR coupling compounds of which the products of the coupling reaction are colorless but which release development inhibitors can also be used instead of DIR couplers.
  • Poly(alkylene oxides) or ether, ester or amide derivatives thereof, thioether compounds, thiomorpholines, quaternary ammonium salt compounds, urethane derivatives, urea derivatives, imidazole derivatives and 3-pyrazolidones, for example, can be included in the photographic emulsions used in the present invention with a view to increasing sensitivity, increasing contrast or accelerating development.
  • Known water soluble dyes for example, oxonol dyes, hemi-oxonol dyes and merocyanine dyes
  • oxonol dyes, hemi-oxonol dyes and merocyanine dyes can also be used jointly as filter dyes or anti-irradiation dyes, or for other purposes, in the silver halide photographic emulsions used in the present invention.
  • known cyanine dyes, merocyanine dyes and hemi-cyanine dyes can be used jointly as spectrally sensitizing dyes.
  • Various surfactants may be included in the photographic emulsions used in the present invention for a variety of purposes, for example, as coating aids or anti-static agents, for improving slip properties, for emulsification and dispersion purposes, for the prevention of sticking or for improving photographic performance (for example, for accelerating development, increasing contrast or increasing sensitivity).
  • the finished emulsion is coated on a suitable support, for example, on baryta paper, resin coated paper, synthetic paper, triacetate film, poly(ethylene terephthalate) film or some other plastic film, or on a glass plate.
  • the silver halide color photographic light-sensitive materials of the present invention may be, for example, color negative films, color photographic light-sensitive materials for photomechanical process (for example, lith films or lith duplicating films), light-sensitive materials for cathode ray tube display purposes (for example, light-sensitive materials for X-ray recording purposes and materials for direct and indirect photographic purposes using a screen), light-sensitive materials for use in silver salt diffusion transfer processes, light-sensitive materials for use in color diffusion transfer processes, light-sensitive materials for use in dye transfer processes (imbibition transfer processes), emulsions for use in a silver dye bleach process, light-sensitive materials as used for recording print-out images, light development type printing (Direct print image) light-sensitive materials, light-sensitive materials for heat development purposes and light-sensitive materials for use with physical development.
  • color negative films for example, color photographic light-sensitive materials for photomechanical process (for example, lith films or lith duplicating films), light-sensitive materials for cathode ray tube display purposes (for example, light-sensitive materials for X-
  • any of the various known light sources such as natural light (daylight), tungsten lamps, florescent lamps, mercury lamps, xenon arc lamps, carbon arc lamps, xenon flash lamps and the flying spot of a cathode ray tube can be used for making an exposure.
  • the exposure time is normally from 1/1000 second to 1 second made using a camera, but of course exposures of duration less than 1/1000 second, for example, exposures of from 10 ⁇ 4 to 10 ⁇ 6 second made using-a xenon strobe lamp or a cathode ray tube, can be used, and exposures of longer duration than 1 second can also be used.
  • the spectral composition of the light which is used to make the exposure can be adjusted, as required, using colored filters.
  • Laser light can also be used for making the exposure.
  • exposures can also be made using the light released by phosphors which have been excited by means of electron beams, X-rays, ⁇ -rays or ⁇ -rays, for example.
  • All of the known methods of processing and the known processing baths can be used for the development processing of light-sensitive materials which have been formed in accordance with the present invention.
  • the photographic processing may involve either processing in which a silver image is formed (black-and-white photographic processing) or processing in which a dye image is formed (color photographic processing), depending on the intended purpose.
  • a processing temperature of from 18°C to 50°C is generally selected, but temperatures below 18°C or above 50°C can be used.
  • the silver halide color photographic light-sensitive materials of the present invention have a dye layer which has an excellent filtering effect, anti-halation effect or light-sensitive emulsion sensitivity controlling effect.
  • the dye layer in a silver halide color photographic light-sensitive material of the present invention contains a dye which has the appropriate spectral absorption, which dyes a specific layer selectively and which does not diffuse into other layers.
  • the silver halide color photographic light-sensitive materials of the present invention have excellent ageing stability and excellent color reproduction.
  • Sample 101 a multi-layer color light-sensitive material comprising an undercoated cellulose triacetate film support having thereon the layers of which the compositions are indicated below, was prepared.
  • the coated amounts shown are the weight of silver in units of g/m in the case of silver halides and colloidal silver, the weight in units of g/m in the case of couplers, additive and gelatin, and the number of mol per mol of silver halide in the same layer in the case of the sensitizing dyes.
  • Fine grain silver bromide as silver Corresponding sphere diameter 0.07 ⁇ m) 0.15 Gelatin 1.0 ExC-4 0.03 Cpd-2 0.2
  • Silver iodobromide emulsion as silver (AgI 8.5 mol%, high internal AgI type, corresponding sphere diameter 1.0 ⁇ m, coefficient of variation of the corresponding sphere diameter 25%, tabular grains, diameter/thickness ratio 3.0) 0.55 Gelatin 0.7 ExS-1 3 ⁇ 10 ⁇ 4 mol ExS-2 1 ⁇ 10 ⁇ 4 mol ExS-3 0.3 ⁇ 10 ⁇ 4 mol ExC-1 0.10 ExC-2 0.05 ExC-4 0.025 Solv-1 0.20
  • Silver iodobromide emulsion as silver (AgI 11.3 mol%, high internal AgI type, corresponding sphere diameter 1.4 ⁇ m, coefficient of variation of the corresponding sphere diameter 28%, tabular grains, diameter/thickness ratio 6.0) 1.29 Gelatin 0.6 ExS-1 2 ⁇ 10 ⁇ 4 mol ExS-2 0.6 ⁇ 10 ⁇ 4 mol ExS-3 0.2 ⁇ 10 ⁇ 4 mol ExC-2 0.08 ExC-4 0.01 ExC-5 0.06 Solv-1 0.12 Solv-2 0.12
  • Silver iodobromide emulsion as silver (AgI 11.3 mol%, high internal AgI type, corresponding sphere diameter 1.4 ⁇ m, coefficient of variation of the corresponding sphere diameter 28%, tabular grains, diameter/thickness ratio 6.0) 1.3 Gelatin 0.8 ExS-5 2 ⁇ 10 ⁇ 4 mol ExS-6 0.8 ⁇ 10 ⁇ 4 mol ExS-7 0.8 ⁇ 10 ⁇ 4 mol ExM-3 0.01 ExM-4 0.04 ExC-4 0.005 Cpd-5 0.01 Solv-1 0.2
  • Silver iodobromide emulsion as Silver (AgI 10 mol%, high internal AgI type, corresponding sphere diameter 0.7 ⁇ m, coefficient of variation of the corresponding sphere diameter 14%, tetradecahedral grains)
  • Silver iodobromide emulsion as silver (AgI 4.0 mol%, high internal AgI type, corresponding sphere diameter 0.4 ⁇ m, coefficient of variation of the corresponding sphere diameter 22%, tetradecahedral grains)
  • Gelatin 1.0 ExS-8 3 ⁇ 10 ⁇ 4 mol ExY-1 0.6 ExY-2 0.02 Solv-1 0.15
  • Silver iodobromide emulsion as silver (AgI 19.0 mol%, high internal AgI type, corresponding sphere diameter 1.0 ⁇ m, coefficient of variation of the corresponding sphere diameter 16%, tetradecahedral grains) 0.19 Gelatin 0.3 ExS-8 2 ⁇ 10 ⁇ 4 mol ExY-1 0.22 Solv-1 0.07
  • Silver iodobromide emulsion as silver (AgI 14.0 mol%, high internal AgI type, corresponding sphere diameter 1.7 ⁇ m, coefficient of variation of the corresponding sphere diameter 28%, tabular grains, diameter/thickness ratio 5.0) 1.4 Gelatin 0.5 ExS-9 1.5 ⁇ 10 ⁇ 4 mol ExY-1 0.2 Solv-1 0.07
  • B-1 total 0.20 g/m
  • 1,2-benzisothiazolin-3-one average about 200 ppm with respect to the gelatin
  • n-butyl p-hydroxybenzoate 1,000 ppm with respect to the gelatin
  • 2-phenoxyethanol 10,000 ppm with respect to the gelatin
  • Samples 102 to 112 were prepared in the same way as sample 101 except that Cpd-1 in the first layer of sample 101 was replaced with Cpd-6, Cpd-7 and Cpd-8 indicated below, and compounds 1, 14, 17, 20 and 21 used in this present invention.
  • the samples 101 to 112 obtained in this way were given a wedge exposure using white light and processed at 38°C in the way indicated below.
  • composition of the processing bath used in each process was as indicated below:
  • the photographic sensitivities of the green-sensitive layers were assessed by measuring the densities of the processed samples so obtained.
  • samples 101 to 112 were stored for 10 days under conditions of 25°C, 60% RH or 50°C, 70% RH and then subjected to the aforementioned bleaching and subsequent processes without being exposed and density measurements were made to assess the changes in density.
  • Table 1 Sample Relative Green Sensitivity* ⁇ D B ** Dye Relationship with the Invention 101 100 0.05 Cpd-1 Comparative Example 102 93 0.10 Cpd-6 Comparative Example 103 93 0.15 Cpd-7 Comparative Example 104 63 0.18 Cpd-8 Comparative Example 105 107 0.01 1 Invention 109 107 0.01 14 Invention 110 107 0.01 17 Invention 111 107 0 20 Invention 112 107 0 21 Invention *: Relative sensitivity taking the sensitivity for sample 101 to be 100 **: (Yellow density on aging at 25°C, 60% RH)-(Yellow density on aging at 50°C, 70% RH)
  • the compounds used in this present invention have excellent oil solubility and there is no migration of the dye during processing or during the long term storage of the light-sensitive material.
  • Sample 201 a multi-layer color light-sensitive material comprising a similar support to that used in Example 1 having thereon layers of which the compositions are indicated below, was prepared.
  • the coated amounts are indicated in the same way as in Example 1.
  • Example 1 Same as the tenth layer in Example 1.
  • B-1 1,2-benzisothiazolin-3-one, n-butyl p-hydroxybenzoate and 2-phenoxyethanol were added to each layer in the same way as in Example 1.
  • sample 202 was prepared in the same way as sample 201 except that the eleventh layer of sample 201 was modified in the way indicated below, 0.05 g/m of Cpd-10 was added to the first layer of sample 201 and the amount of Solv-l in the first layer of sample 201 was changed from 0.01 g/m to 0.10 g/m.
  • sample 203 was prepared in the same way as sample 202 except that Cpd-9 in the eleventh layer of sample 202 and Cpd-10 in the first layer of sample 202 were replaced by compound 44 and Cpd-11, respectively.
  • samples 205 and 206 were prepared in the same way as sample 203 except that Cpd-11 in the first layer of sample 203 was replaced by compound 32 and compound 5 employed in the present invention, respectively.
  • samples 207 and 208 were prepared in the same way as sample 203 except that compound 44 in the eleventh layer of sample 203 was changed to compound 39, and Cpd-11 in the first layer of sample 203 was changed to compound 1 or compound 37, respectively.
  • Samples 201 to 208 obtained in this way were exposed and processed in the same way as described in Example 1.
  • a Macbeth chart was photographed using samples 201, 202 and 207 prepared in Example 2 and, after processing in the way described in Example 2, the images were printed onto color paper using an auto-printer.

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Claims (9)

  1. Matériau photosensible photographique couleur à l'halogénure d'argent qui comprend au moins un colorant qui est insoluble dans l'eau et qui est représenté par la formule (3) :
    Figure imgb0094
     où R⁷ représente un groupe alkyle ; R⁸ et R⁹ peuvent être identiques ou différents, chacun représentant un groupe alkyle, et un cycle de cinq ou six maillons peut être formé par R⁸ et R⁹ ; R¹⁰ représente un atome d'hydrogène, un atome d'halogène, un groupe alkyle, un groupe alcoxy, un groupe hydroxyle, un groupe amino, un groupe carbamoyle, un groupe sulfamoyle ou un groupe alcoxycarbonyle ; à la condition qu'au moins l'un des groupes R⁷, R⁸, R⁹ et R¹⁰ contient une chaîne alkyle qui a au moins 4 atomes de carbone.
  2. Matériau photosensible photographique couleur à l'halogénure d'argent selon la revendication 1, qui contient en outre au moins un colorant qui est insoluble dans l'eau et est représenté par la formule (2) :
    Figure imgb0095
     où X et Y peuvent être identiques ou différents, chacun représentant un groupe cyano, un groupe carboxyle, un groupe alkylcarbonyle, un groupe arylcarbonyle, un groupe alcoxycarbonyle, un groupe aryloxycarbonyle, un groupe carbamoyle, un groupe sulfonyle ou un groupe sulfamoyle, à la condition que sont exclus les cas où les combinaisons suivantes de X et Y sont réalisées (groupe cyano, groupe arylcarbonyle), (groupe cyano, groupe alkylcarbonyle) ou (groupe cyano, groupe sulfonyle); R³ et R⁴ peuvent être identiques ou différents, chacun représentant un atome d'hydrogène, un atome d'halogène, un groupe alkyle, un groupe alcoxy, un groupe hydroxy, un groupe carboxyle, un groupe amino, un groupe carbamoyle, un groupe sulfamoyle ou un groupe alcoxycarbonyle ; R⁵ et R⁶ peuvent être identiques ou différents, chacun représentant un atome d'hydrogène, un groupe alkyle ou un groupe aryle, et R⁵ et R⁶ peuvent former un cycle à 5 ou 6 maillons; et R³ ou R⁵, ou R⁴ et R⁶ peuvent être reliés pour former un cycle de 5 ou 6 maillons.
  3. Matériau photosensible photographique couleur à l'halogénure d'argent selon la revendication 2, où le rapport molaire du colorant de formule (3) au colorant de formule (2) ne dépasse pas 1 quand le colorant de formule (3) est utilisé comme colorant de correction de couleur.
  4. Matériau photosensible photographique couleur à l'halogénure d'argent selon la revendication 2, où ledit colorant qui est représenté par la formule (2) est représenté par la formule (4) :
    Figure imgb0096
     où X représente un groupe alkylcarbonyle, un groupe arylcarbonyle et R³ à R⁶ ont la signification donnée à la revendication 2.
  5. Matériau photosensible photographique couleur à l'halogénure d'argent selon la revendication 1 ou 2, où ledit colorant qui est représenté par la formule (3) est utilisé en une quantité de 0,01 à 0,7 g/m de matériau photosensible.
  6. Matériau photosensible photographique couleur à l'halogénure d'argent selon la revendication 2, où ledit colorant qui est représenté par la formule (2) est utilisé en une quantité comprise entre 0,01 et 0,7 g/m de matériau photosensible.
  7. Matériau photosensible photographique couleur à l'halogénure d'argent selon la revendication 1 ou 2, où ledit colorant qui est représenté par la formule (3) est ajouté dans une ou des couches d'émulsion insensibles à la lumière formées entre le support et la couche d'émulsion sensible au rouge.
  8. Matériau photosensible photographique couleur à l'halogénure d'argent selon la revendication 2, où ledit colorant qui est représenté par la formule (2) est ajouté dans une ou des couches d'émulsion insensibles à la lumière fournies en plus de la couche d'émulsion sensible au vert depuis le support et ledit colorant qui est représenté par la formule (3) est ajouté dans une ou des couches d'émulsion insensibles à la lumière fournies entre le support et une couche d'émulsion sensible au rouge.
  9. Matériau photosensible photographique couleur à l'halogénure d'argent selon la revendication 2, où R⁷ représente un groupe ayant 4 atomes de carbone ou plus.
EP90114522A 1989-08-11 1990-07-27 Matériaux photographiques couleur à l'halogénure d'argent sensibles à la lumière Expired - Lifetime EP0412379B1 (fr)

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JP209315/89 1989-08-11
JP209314/89 1989-08-11
JP20931489A JPH0372340A (ja) 1989-08-11 1989-08-11 ハロゲン化銀写真感光材料
JP20931589A JPH0372342A (ja) 1989-08-11 1989-08-11 ハロゲン化銀写真感光材料

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EP0412379B1 true EP0412379B1 (fr) 1996-05-15

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US5776667A (en) * 1996-01-12 1998-07-07 Agfa Ag Color photographic recording material having a yellow filter layer which contains an arylidene dye of isoxazolone as the yellow filter dye
JP3999304B2 (ja) * 1996-09-03 2007-10-31 富士フイルム株式会社 アリーリデン化合物およびハロゲン化銀写真感光材料
JP2009263517A (ja) * 2008-04-25 2009-11-12 Fujifilm Corp アリーリデンイソオキサゾロン色素、着色組成物、感熱転写記録用インクシートおよび感熱転写記録方法
JP5878356B2 (ja) 2011-09-30 2016-03-08 富士フイルム株式会社 着色組成物、および画像表示構造

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0274723A1 (fr) * 1986-12-23 1988-07-20 EASTMAN KODAK COMPANY (a New Jersey corporation) Colorant filtre pour élément photographique
EP0401709A2 (fr) * 1989-06-05 1990-12-12 Fuji Photo Film Co., Ltd. Matériel photographique sensible aux rayons X

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DD131177A1 (de) * 1977-05-24 1978-06-07 Reinhard Stolle Verfahren zur herstellung alpha-substituierter cinnamylidenfarbstoffe
JPH01154149A (ja) * 1987-12-11 1989-06-16 Fuji Photo Film Co Ltd ハロゲン化銀写真感光材料

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0274723A1 (fr) * 1986-12-23 1988-07-20 EASTMAN KODAK COMPANY (a New Jersey corporation) Colorant filtre pour élément photographique
EP0401709A2 (fr) * 1989-06-05 1990-12-12 Fuji Photo Film Co., Ltd. Matériel photographique sensible aux rayons X

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DE69026990T2 (de) 1996-11-14
DE69026990D1 (de) 1996-06-20

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