US3873324A - Spectrally sensitized silver halide photographic emulsion - Google Patents

Spectrally sensitized silver halide photographic emulsion Download PDF

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US3873324A
US3873324A US447114A US44711474A US3873324A US 3873324 A US3873324 A US 3873324A US 447114 A US447114 A US 447114A US 44711474 A US44711474 A US 44711474A US 3873324 A US3873324 A US 3873324A
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silver halide
halide photographic
photographic emulsion
methyl
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Masanao Hinata
Haruo Takei
Keisuke Shiba
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Fujifilm Holdings Corp
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Fuji Photo Film Co Ltd
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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
    • G03C1/28—Sensitivity-increasing substances together with supersensitising substances
    • G03C1/29—Sensitivity-increasing substances together with supersensitising substances the supersensitising mixture being solely composed of dyes ; Combination of dyes, even if the supersensitising effect is not explicitly disclosed

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  • Keisuke Shiba all of Kanagawa, Japan Assignee: Fuji Photo Film Co., Ltd.
  • a further object of the present invention is to selec- PHOTOGRAPHIC EMULSION tively find supersensitizing dyes which, when incorporated in one layer of a multi-layered light sensitive ma- BACKGROUND OF THE INVENTION terial to spectrally sensitize the layer selectively so as 1.
  • the present invention relates to asilver halide photovention, do not diffuse into adjacent layers to cause graphic emulsion which is spectrally sensitized in a spesensitization therein. cific wave-length region by supersensitization and, A still further object of the present invention is to more particularly, it is concerned with a silver halide find sensitizing dyes which are more selective, which photographic emulsion spectrally sensitized in a wavecause less color stain after development-processing and length region of from 580 nm to 640 nm. which cause less reduction in sensitivity even upon 2.
  • Description of the Prior Art storage after production of the light sensitive material Commonly used photographic light-sensitive materi- (spectrally sensitized by the dyes).
  • sensitizing dyes are being studied and selected wherein 2, represents the atoms necessary to form a for use.
  • Z repproducibility it is not preferable to impart high sensiresents the atoms necessary to form a benzoselenazole tivity too far in the longer wave length region, e.g., ring;
  • A represents a hydrogen atom or an alkyl group; longer than 660 nm (wave length of the sensitization R1 and R2 each represent an alkyl group or a substimaximum) or, conversely, to impart sensitivity only in tuted alkyl group, at least O Of 1 and 2 being a a too short wave length region, e.g., less than 580 nm d
  • a sulfo-substituted alkyl group represents an acid
  • X represents an acid
  • m represents 1 or 2 and, when the dye art. it has been difficult to selectively increase the sensif rms an in rnal alt t in -lik Structure), H1 ptivity in the wave length region ranging from 580 nm to resents l; a d at least One carbocyanine dye repre- 640 nm and the solution of this problem has been an Se ed y the general formula important subject in this art.
  • Z and Z each represent the atoms necessary provide a novel supersensitizing combination to selecto form a halogen-substituted benzimizadole nucleus; tively increase the sensitivity in the wave length region R, and R, each represents an alkyl group or a substiranging from 580 nm to 640 nm.
  • Another object of the present invention is to provide droxyalkyl group, a carboxy-substituted alkyl group or a supersensitizing combination which mitigates the rea sulfo-substituted alkyl group;
  • X represents an acid duction in sensitivity experienced in conventional comanion; and
  • n represents 1 or 2 and, when the dye forms binations of supersensitizing dyes.
  • an internal salt, n represents 1.
  • FIGS. 1 17 are spectrograms of photographic materials as described in the Examples and FIG. 18 showsthe per cent transmission curve of the filters used in the Examples.
  • substituents which can be present on the Z, or Z containing heterocyclic nucleus are a halogen atom (e.g., chlorine, fluorine, bromine), a lower alkyl group preferably having no more than 4 carbon atoms in the carbon chain (e.g., methyl, ethyl, etc.), an alkoxy group (e.g., methoxy, ethoxy, etc.), an alkoxycarbonyl group (eg, methoxycarbonyl, etc.), a trifluoromethyl group, a hydroxy group and a carboxy group.
  • halogen atom e.g., chlorine, fluorine, bromine
  • a lower alkyl group preferably having no more than 4 carbon atoms in the carbon chain e.g., methyl, ethyl, etc.
  • an alkoxy group e.g., methoxy, ethoxy, etc.
  • an alkoxycarbonyl group eg, methoxycarbon
  • the heterocyclic ring formed by Z includes, e.g., benzothiazole, 5-chlorobenzothiazole, 5- bromobenzothiazole, S-fluorobenzothiazole 5 methylbenzothiazole, 5-methoxybenzothiazole, 5-
  • l-methyl-5-chlorobenzimidazole e.g., l-methyl-5-chlorobenzimidazole, l-methyl-5- fluorobenzimidazole, l-methyl-5,6- dichlorobenzimidazole, I-ethyl-S- chlorobenzimidazole, I-ethyl-5-fluorobenzimidazole, l-methyl-S ,o-dichlorobenzimidazole, l-ethyl5 ,6- difluorobenzimidazole.
  • A represents, for example, a hydrogen atom, an alkyl group, preferably having up to 3 carbon atoms, e.g., a methyl group, and ethyl group, a propyl group, or the like.
  • R R R and R each represents an alkyl group such as an unsubstituted alkyl group (e.g., a methyl group, an ethyl group, a propyl group), a hydroxyalkyl group (e.g., a Z-hydroxyethyl group, a 3-hydroxypropyl group, etc.), a carboxy-substituted alkyl group (e.g., a Z-carboxyethyl group, a 3-carboxypropyl group, a 4- carboxybutyl group.
  • an unsubstituted alkyl group e.g., a methyl group, an ethyl group, a propyl group
  • a hydroxyalkyl group e.g., a Z-hydroxyethyl group, a 3-hydroxypropyl group, etc.
  • a carboxy-substituted alkyl group e.g., a Z-carboxyethyl group
  • a sulfo-substituted alkyl group e.g., a 2-sulfoethyl group, a 3-sulfopropyl group. a 3-sulfobutvl group. a 2I3-sulfopropoxvlethvl group, a 2-hydroxy-3-sulfopropyl group, a 3-sulfopropoxyethoxyethyl group, etc.
  • an acetoxyalkyl group e.g., acetoxyethyl, etc.
  • a cyanoalkyl group e.g., cyanopropyl, etc.
  • carbamoylalkyl group e.g., B-carbomoylethyl, etc.
  • a morpholinocarbanylalkyl group e.g., B-(4-morpholinocarbonyl)ethyl, etc.]
  • X each represents an acid anion commonly employed in cyanine dye salts, such as an iodide ion, a bromide ion, a chloride ion, a p-toluenesulfonate ion, a benzenesulfonate ion, an ethylsulfate ion, a perchlorate ion, a rhodanide ion, or the like.
  • cyanine dye salts such as an iodide ion, a bromide ion, a chloride ion, a p-toluenesulfonate ion, a benzenesulfonate ion, an ethylsulfate ion, a perchlorate ion, a rhodanide ion, or the like.
  • one of R and R is a hydroxyalkyl group, a carboxysubstituted alkyl group or a sulfo-substituted alkyl group and the other is a carbamoylalkyl group, an acetoxyalkyl group, a morpholinocarbonyl group. a cyanoalkyl group, a morpholinosulfonyl group. or an allyl group; or at least one of the nitrogen atoms at the 1- position ofthe dye of general formula (II) is substituted with an aryl group. an acetoxyalkyl group or an allyl group. Incidentally.
  • a chemical structural feature of the sensitizing dyes represented by the general formula (I) is that they are carbocyanine dyes wherein one or, preferably, two of the substitutents connected to the nitrogen atom or atoms in the nitrogen-containing heterocyclic nueleus or nuclei are hydroxyalkyl groups, carboxysubstituted alkyl groups or sulfo-substituted alkyl groups. These dyes show maximum sensitivity in the wave length region ranging from about 600 nm to about 670 nm. Furthermore, they have the feature that, when used in combination with the dye represented by the general formula (II), they increase the spectral sensitivity while maintaining the light sensitivity maximum at a wave length of from about 600 nm to about 630 nm.
  • a chemical structural feature of the sensitizing dyes represented by the general formula (II) is that they are imidazolocarbocyanines having a hydroxyalkyl group, a carboxy-substitutcd alkyl group or a suIfo-substituted alkyl group as the substituent connected to the nitrogen atom in the nitrogencontaining heterocyclic nucleus.
  • These dyes show maximum sensitivity in the wave length region ranging from about 570 to about 585 nm and scarcely cause color stain after development processing.
  • the supersensitizing action by the combined use of the dyes of the present invention strongly counteracts prevention of spectral sensitization due to presence of a color coupler.
  • the desensitization conventionally experienced in the combined use of a sensitizing dye and a coupler, is extremely small.
  • these dyes rarely diffuse into adjacent emulsion layers when applied to one light sensitive layer of a multi-layer light sensitive material. they never sensitize the adjacent layers (silver halide emulsion layers).
  • the supersensitizing technique in accordance with the present invention are useful for the production of ortho-pan type light sensitive emulsions, light sensitive emulsions for mult-layer coupler in the emulsion type color films, particularly, reversal color films and negative color films, for example, as disclosed in US. Pat. Nos. 2,698.794; 2,474.293; 2,600,788; 3,311,476; 3.458.315; 3,214,437 and 3,253,924.
  • sensitizing dyes which can be used in the present invention are illustrated below. However, the present invention is not limited to the dyes specifically described below.
  • the silver halide photographic emulsions which can be used in the present invention are those produced in a conventional manner and containing silver chloride, silver bromide, silver iodide, silver chlorobromide, silver chloroiodide, silver bromoiodide, silver chlorobromoiodide or mixed silver halide grains thereof, which are precipitated through a single jet method, a double jet method, or a combination of these methods followed by ripening.
  • a preferred silver halide is silver bromoiodide or silver chlorobromoiodide and a preferred mean diameter of the grains (measured by, e.g., a projected area method or a number average method) is from 0.04 micron to 2 microns.
  • a preferred mean diameter of the grains is from 0.04 micron to 2 microns.
  • Suitable examples of and the preparation thereof are disclosed in U.S. Pat. Nos. 3,217,157; 2,222,264; 3,320,069; 2,592,250; 3,206,313; and 3,367,778 and Belgian Pat. No. 704,255; U.S. Pat. NO.
  • the emulsion can contain a sulfur sensitizer such as allylthiocarbamide, thiourea, sodium thiosulfate or cystine; a noble metal sensitizer such as potassium chloroaurate, aurous thiosulfate, or potassium chloropalladate; a reduction sensitizer such as tin chloride, phenylhydrazine or reductone; and the like.
  • the emulsion can contain such a sensitizer as a polyoxyethylene derivative, a polyoxypropylene derivative, a quaternary ammonium group-containing derivative or the like.
  • the emulsion can contain an antifogging agent such as nitrobenzimidazole or ammonium chloroplatinate, and a stabilizing agent such as 4-hydroxy-6-methyl-l,3,3a,7-tetrazaindene.
  • an antifogging agent such as nitrobenzimidazole or ammonium chloroplatinate
  • a stabilizing agent such as 4-hydroxy-6-methyl-l,3,3a,7-tetrazaindene.
  • the emulsion can contain a hardener, such as formaldehyde, chrome alum, l-hydroxy-3,5- dichlorotriazine sodium salt, glyoxal, dichloroacrolein, etc., and a coating aid such as saponin, sodium alkylbenzenesulfonate, etc.
  • a hardener such as formaldehyde, chrome alum, l-hydroxy-3,5- dichlorotriazine sodium salt, glyoxal, dichloroacrolein, etc.
  • a coating aid such as saponin, sodium alkylbenzenesulfonate, etc.
  • hardeners are aldehyde series compounds such as formaldehyde, glutaraldehyde and halocarboxyaldehydes (e.g., mucochloric acid); ketones such as diacetyl and cyclopentanedione; active halogen-containing compounds such as bis(2-ch1oethyl urea), 2-hydroxy-4,6-dichloro-l ,3,5- triazine and those compounds as disclosed in U.S. Pat.
  • aldehyde series compounds such as formaldehyde, glutaraldehyde and halocarboxyaldehydes (e.g., mucochloric acid)
  • ketones such as diacetyl and cyclopentanedione
  • active halogen-containing compounds such as bis(2-ch1oethyl urea), 2-hydroxy-4,6-dichloro-l ,3,5- triazine and those compounds as disclosed in U.S. Pat
  • active olefin-containing compounds such as divinylsulfone, 5-acetyl-l,3- diacryloylhexahydro-l,3,5-triazine and those compounds as disclosed in U.S. Pat. Nos. 3,635,718; 2,232,763; 3,490,911 and 3,642,486 and British Pat. No. 994,869; N-methylol compounds such N-hydroxymethylphthalimide and those compounds as disclosed in Us Pat. Nos. 2,732,316 and 2,586,168; isocyanates as disclosed in U.S. Pat. Nos. 3,103,437; aziridines as disclosed in U.S. Pat. Nos.
  • dioxane derivatives such as dihydroxydioxane and dichlorodioxane and inorganic hardeners such as chrom alum and zirconium sulfate, precursors of the above-described materials such as addition compounds of an alkali metal bisulfite and an aldehyde, methylol derivatives of hydrazine, and primary aliphatic nitro alcohols and those compounds as disclosed in U.S. Pat. Nos. 3,288,775; 3,017,280 and 2,983,611 and British Pat. No. 1,167,207.
  • any of the known surface active agents as a coating aid can be employed and sepcifically, anionic surface active agents containing acidic groups such as a carboxylic acid group, a sulfonic acid group, a phosphoric acid group, a sulfate group, a phosphate group, etc., ampholytic surface active agents of carboxylic acid type, sulfonic acid type, sulfate type or phosphate type; nonionic surface active agents of the polyalkyleneoxide series or the polyglycerin series; and natural surface active agents such as saponin, are preferably used. Suitable such materials and the amounts thereof generally suitable for use are disclosed for example, in
  • the silver halide emulsion used in the present invention contains a color coupler and a dispersing agent therefor.
  • a cyan coupler is particularly preferred.
  • the phenolic couplers as described in U.S. Pat. No. 2,698,794 and the naphtholic couplers as describedin U.S. Pat. No. 2,474,293 are particularly useful.
  • the couplers described in US. Pat. No. 2,600,788, British Pat. No. 904,852 and Japanese Patent Publication Number 603 1/65 the a-naphtholic cyan couplers and the phenolic cyan couplers described in, e.g., U.S. Pat. Nos. 3,311,476; 3,458,315; 3,214,437 and 3,253,924 can be used.
  • the couplers represented by the following structural formulae can be used, all of which are known com- Nos. 3,288,775 and 2,732,303 and British Pat. Nos. pounds.
  • Photographic emulsions spectrally sensitized with the dye combinations of the present invention can contain various colloids alone or in combination as vehicles or binding agents.
  • Suitable hydrophilic materials include both naturally-occurring substances such as proteins, for example, gelatin, gelatin derivvtives suchas phthaloylated gelatin or malonoylated gelatin, cellulose derivatives such as hydroxyethyl cellulose or carboxy methyl cellulose, polysaccharides such as dextran, gum arabic and the like; and synthetic polymeric substances such as water soluble polyvinyl compounds, c.g., polyvinyl alcohol, poly(vinylpyrrolidone), acrylamide polymers, polystyrenesulfonic acid, or other synthetic polymeric compounds such as dispersed vinyl compounds in latex form, and particularly those which increase the dimensional stability of the photographic materials.
  • proteins for example, gelatin, gelatin derivvtives suchas phthaloylated gelatin or malonoylated gelatin, cellulose derivatives such as hydroxyethyl cellulose or carboxy methyl cellulose, polysaccharides such as dextran, gum arabic and
  • Suitable synthetic polymers include those described, for example, in US. Pat. Nos. 3,142,568; 3,193,386; 3,062,674; 3,220,844; 3,287,289 and 3,411,911. Particularly effective are those water insoluble polymers of alkyl acrylates and methacrylates, acrylic acid, sulfoalkyl acrylates or methacrylates, those which have cross linking sites which facilitate hardening or curing and those having recurring sulfobetaine units as described in Canadian Pat. No. 774,054.
  • the matting agent which can also be present in the emulsion there are preferably used silver halide grains of a suitable grain size; inorganic compounds such as silica, strontium barium sulfate, etc.; water-dispersable vinyl polymers such as polymethyl methacrylate, etc.
  • plasticizers which can be present in the emulsion are waxes such as liquid paraffin, higher fatty acid esters, etc.; polyfluorinated hydrocarbons or derivatives thereof;
  • silicones such as polyalkylpolysiloxane, polyarylpolysiloxane, polyalkylarylpolysiloxane or the alkylene oxide adduct derivatives thereof; and the like are preferably used.
  • the finished emulsion is applied to a suitable support such as baryta paper, a resin-coated paper, a synthetic paper, a triacetate film, a polyethylene terephthalate film, a gl'ass plate or other plastic bases.
  • a suitable support such as baryta paper, a resin-coated paper, a synthetic paper, a triacetate film, a polyethylene terephthalate film, a gl'ass plate or other plastic bases.
  • the sensitizing dyes of the general formula (1) and (11) used in the present invention are added as a solution prepared by dissolving the dyes in water or a water-miscible organic solvent such as methanol, ethanol, t yl. qsq vst2y isli OI sl e- Each of these dyes is used in the amount usually employed in supersensitization, c.g., 5 X 10 mol to l X 10 mol, preferably 1 X 10" mol to 1 X 10' mol, per 1 mol of silver.
  • a preferred molar ratio of the amount of the dye represented by the general formula (11) to that of the dye represented by the general formula (1) ranges from 1:10 to 10:], particularly 1:5 to 5:1 and more particularly 1:3 to 3:].
  • the dyes to be used in the present invention can be used for spectral sensitization according to German OLS Pat No. 2,104,284 and US. Pat. No. 3,649,286.
  • each emulsion portion was added 10 cc of a 0.1 by weight aqueous solution of 4-hydroxy-6-methyl- I,3,3a,7-tetrazaindene, 10 cc of a 1 by weight aqueous solution of I-hydroxy-3,5-dichlorotriazole sodium salt and 10 cc of a I by weight aqueous solution of soidum dodecylbenzenesulfonate, and stirred.
  • Each of the thus finished emulsion portions was applied to a cellulose triacetate film base in a dry thickness of 5 p. and then dried. Thus, light sensitive material samples were obtained. Each of these film samples was cut into. strips.
  • the spectral transmission curves of filter Sp-I, filter Sc-SO and filter 80-56 are shown in FIG. 18.
  • the spectrograms obtained are shown in FIGS. 1 to 10. From the values given in Table I and from the spectrograms. it can be seen thatthe effects of the combination of dyes of the present invention showing a supersensitizing action are excellent.
  • FIG. 2 I14 100 90 0.08 FIG. 2 4 (I -A) I (II-B) 4 (6) 2 570 370 92 0.10 FIG. 2-5 3 (I) I I24 53 86 0.07
  • FIG. 3 6 4 200 86 70 0.07 (I) I (II B) 4 328 I96 78 0.09
  • FIG. 3 7 4 (3 I 56 25 80 0.07 2 I10 46 0.09 4 I17 49 68 0.11 FIG.4-8 (I-A) l (3) v4 280 I60 7 0.10
  • FIG.5-I1 I 100 I00 88 0.07 FIG. 5 10 2 I68 146 70 0.07 4 250 230 60 0.07 (I-E) I (II-B) 4 400 250 92 0.10 FIG.5-I1
  • Each of the thus finished emulsion portions was applied to a cellulose triacetate film base in a dry thickness of p. followed by drying. Thus, light sensitive material samples were obtained.
  • Each of these film samples was cut into strips.
  • One of the strips was wedgewise exposed through a red filter Sc-56 using a sensitometer containing a light source of a color temperature of 5400K.
  • FIG. 10 1 4 405 358 92 0.08 FIG. 9 20 11 (I A) I (ll E1 4 432 280 96 0.08 FIG. l0 21 2 4 128 80 40 0.10 FIG. 10 22 100 0.07
  • N-Methyl-p-aminophenol 4.5 g 20 Hydroquinone 4.5 g 80 grams of a cyamne coupler, l-hydroxy-4- Sodium Sultite (anhydrous) 50 g maleimidO-Z-naphthamide, was completely dissolved in gg tgg g gg if g a mixed solution of [00 cc of tricresyl phosphate and Potassium Thiocyanate 2 g 50 cc of ethyl acetate. Furthermore, 2 g of sorbitan Wate'm make I I monolaurate was dissolved therein. The resulting solu- 25 The strip was then color development-processed at 24C for 15 minutes in a color developer having the following composition followed by washing, bleaching, washing, fixing and washing. Thus, a color positive image was obtained.
  • the one remaining strip was exposed using a grating spectrophotograph having a 2660K tungsten light source to obtain spcctrograms.
  • the thus obtained spectrograms are shown in FIGS. 11 to 17.
  • FIG. l4-3l 5 (l-E) I I00 007 FIG. 15-32 2 I40 0.07 (I-E) I (II-B) 4 I80 0.08 FlG.l5-33 2 4 200 0.08 6 (l-E) l (II-B) 4 (6) 2 250 0.08 7 (2) I 2 0.07
  • sensitizing dyes of the present invention having sensitizing action is useful for spectrally sensitizing a silver halide emulsion using for a red-sensitive layer in color light sensitive materials such as a color negative light sensitive material and a color reversal light sensitive material; a silver halide emulsion for use in a plate-making light sensitive material; and a silver halide emulsion for use in a light sensitive material for microsecond exposure, particularly, a CRT sensitive material, a light sensitive material for holography and a light sensitive material for use in a facsimile system.
  • color light sensitive materials such as a color negative light sensitive material and a color reversal light sensitive material
  • a silver halide emulsion for use in a plate-making light sensitive material
  • a silver halide emulsion for use in a light sensitive material for microsecond exposure particularly, a CRT sensitive material, a light sensitive material for holography and a light sensitive material for use in a facsi
  • a magenta or red outer filter above or adjacent to the red-sensitive silver halide emulsion layer obtained by the present invention so as to impart the effect of actually reducing the greensensitivity in contrast to the red-sensitivity.
  • Z forms a benzol5 selenazole ring which is unsubstituted or substituted with a methyl group, an ethyl group, a methoxy group, a phenyl group or a chloride atom at the 5-position;
  • R, and R each is a sulfosubstituted alkyl group, a carboxy-substituted alkyl group or a hydroxyalkyl group; and A is a methyl group.
  • a color light sensitive material comprising a support having thereon the silver halide photographic emulsion as described in claim I.
  • alkyl group for R, R is an unsubstituted alkyl group, a hydroxyalkyl group, a carboxy-substituted alkyl group, a sulfo-substituted alkyl group, an acetoxyalkyl group, a cyanoalkyl group, a carbamoylalkyl group, a morpholinocarbonyl group, an allyl group or a morpholinosulfonylalkyl group.
  • Z is a benzothiazole, 5- chlorobenzothiazole, S-bromobenzothiazole, 5- fluorobenzothiazole, SI-methylbenzothiazole, 51- methoxybenzothiazole, S-methylcarbonylbenzothiazole, S-methoxycarbonylbenzothiazole, S-carboxybenzothiazole, S-hydroxybenzothiazole, 5- trifluoromethylbenzothiazole, 5-cyanobenzothiazole, 5,-dimethylbenzothiazole, 5,6-dimethoxybenzothiazole, 5,6-dichlorobenzothiazole, ,B-naphthothiazole, benzoselenazole, 5-chlorobenzoselenazole, 5- bromoselenazole, 5-methylbenzoselenazole, 51- methoxybenzoselenazole or ,B-naph
  • 3carboxypropyl group a 4-carboxybutyl group, a 2- sulfoethyl group, a 3-sulfopropyl group, a 3-sulfobutyl group, a 2-[3-sulfopropoxy1ethyl group, a 2-hydroxy3- sulfopropyl group, a 3-sulfopropoxyethoxyethyl group, an acetoxyethyl group, a cyanopropyl group, a fi-carbamoylethyl group, a ,8-(4-morpholinocarbonyl)ethyl group, or a 6-(4-morpholinosulfonyl)butyl group.

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DE2615971A1 (de) * 1975-04-14 1976-10-28 Konishiroku Photo Ind Lichtempfindliches farbphotographisches silberhalogenid-aufzeichnungsmaterial
US4040839A (en) * 1975-05-19 1977-08-09 Fuji Photo Film Co., Ltd. Direct-positive process utilizing a supersensitized silver halide emulsion
US4138266A (en) * 1974-12-24 1979-02-06 Fuji Photo Film Co., Ltd. Method for spectrally sensitizing photographic light-sensitive emulsions
US4179296A (en) * 1975-12-29 1979-12-18 Fuji Photo Film Co., Ltd. Silver halide photographic emulsion
US4510235A (en) * 1983-04-28 1985-04-09 Fuji Photo Film Co., Ltd. Silver halide photographic emulsions

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JPH03107139A (ja) * 1989-09-20 1991-05-07 Konica Corp 色相再現性に優れたカラー写真感光材料
EP1624337A3 (en) * 2004-08-02 2006-04-19 Fuji Photo Film Co., Ltd. Silver halide holographic sensitive material and system for taking holographic images by using the same

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US3666480A (en) * 1969-10-29 1972-05-30 Fuji Photo Film Co Ltd Spectrally sensitized silver halide photographic emulsion
US3672898A (en) * 1969-09-29 1972-06-27 Eastman Kodak Co Multicolor silver halide photographic materials and processes
US3702251A (en) * 1967-12-07 1972-11-07 Konishiroku Photo Ind Light-sensitive silver halide photographic emulsion for microfilm use
US3799783A (en) * 1972-01-03 1974-03-26 Polaroid Corp Silver halide emulsion containing sensitizing dye combination

Patent Citations (4)

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Publication number Priority date Publication date Assignee Title
US3702251A (en) * 1967-12-07 1972-11-07 Konishiroku Photo Ind Light-sensitive silver halide photographic emulsion for microfilm use
US3672898A (en) * 1969-09-29 1972-06-27 Eastman Kodak Co Multicolor silver halide photographic materials and processes
US3666480A (en) * 1969-10-29 1972-05-30 Fuji Photo Film Co Ltd Spectrally sensitized silver halide photographic emulsion
US3799783A (en) * 1972-01-03 1974-03-26 Polaroid Corp Silver halide emulsion containing sensitizing dye combination

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4138266A (en) * 1974-12-24 1979-02-06 Fuji Photo Film Co., Ltd. Method for spectrally sensitizing photographic light-sensitive emulsions
DE2615971A1 (de) * 1975-04-14 1976-10-28 Konishiroku Photo Ind Lichtempfindliches farbphotographisches silberhalogenid-aufzeichnungsmaterial
US4040839A (en) * 1975-05-19 1977-08-09 Fuji Photo Film Co., Ltd. Direct-positive process utilizing a supersensitized silver halide emulsion
US4179296A (en) * 1975-12-29 1979-12-18 Fuji Photo Film Co., Ltd. Silver halide photographic emulsion
US4510235A (en) * 1983-04-28 1985-04-09 Fuji Photo Film Co., Ltd. Silver halide photographic emulsions

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FR2219443A1 (en, 2012) 1974-09-20
GB1413645A (en) 1975-11-12
DE2409620A1 (de) 1974-09-05
JPS49114419A (en, 2012) 1974-10-31

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