US3632373A - Method for preparing silver halide layers having substantially uniform image contrast - Google Patents

Method for preparing silver halide layers having substantially uniform image contrast Download PDF

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US3632373A
US3632373A US717920A US3632373DA US3632373A US 3632373 A US3632373 A US 3632373A US 717920 A US717920 A US 717920A US 3632373D A US3632373D A US 3632373DA US 3632373 A US3632373 A US 3632373A
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coupler
group
couplers
pyrazolone
photographic
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Reid J O'connell
John H Van Campen
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Eastman Kodak Co
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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
    • G03C7/3225—Combination of couplers of different kinds, e.g. yellow and magenta couplers in a same layer or in different layers of the photographic material
    • 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

Definitions

  • One object of this invention is to provide novel photographic elements and processes.
  • Another object of this invention is to provide photographic silver halide emulsion layers which have essentially uniform contrast throughout.
  • a further object of this invention is to provide a novel method for preparing photographic silver halide emulsions containing color former, which emulsions provide substantially uniform contrast.
  • a photographic element comprising a support having coated thereon a photographic silver halide emulsion layer containing photographic image-forming coupler, the ratio of silver halide to photographic image-forming coupler varying in different areas of said layer, said emulsion layer containing a development inhibitor-releasing coupler, the ratio of development inhibitor-releasing coupler to photographic image-forming coupler being essentially constant throughout the layer. It has been found that such photographic layers exhibit substantially uniform contrast throughout. Similar photographic elements, which do not contain development inhibitor-releasing coupler, exhibit objectionably high variations in contrast from area to area in the layer.
  • the improvement in the method of preparing light-sensitive photographic coatings wherein a photographic image-forming coupler and a photographic silver halide emulsion are separately introduced into a mixing zone, admixed and coated onto a support, and the ratio of photographic image-forming coupler to silver halide varies during the coating operation, the improvement is provided which comprises introducing into said mixing zone a development inhibitor-releasing coupler and maintaining an essentially constant ratio of development inhibitor-releasing coupler to photographic image-forming coupler throughout the coating operation.
  • Such processes result in photographic layers which exhibit substantially uniform contrast throughout.
  • the process of this invention is conveniently carried out by separately metering a photographic emulsion (which can be separately sensitized) and the combination of photographic image-forming coupler and development inhibitor-releasing coupler (which can be incorporated in a hydrophilic colloid that can also contain other emulsion addenda); mixing the emulsion and coupler combination; and coating the mixture on a support, preferably substantially immediately after mixing as described by Collins et al., in US. Pat. No. 2,912,343.
  • a plurality of such emulsions can have the coupler combination incorporated therein and the resulting emulsion can be coated simultaneously, as described by Russell in US. Pat. No. 2,761,791, issued Sept. 4, 1956, which disclosure is incorporated herein by reference.
  • the present invention can be practiced with any photographic emulsion-coating process which tends to result in photographic silver halide emulsion layers having varying ratios of silver (or silver halide) to image-forming coupler in various areas of the element.
  • the invention is particularly useful in coating processes of the type wherein a silver halide emulsion (which silver halide emulsion can be spectrally sensitized) has photographic image-forming coupler admixed therewith just before the emulsion is coated onto a support.
  • Such processes are described in detail by Collins et al., in US. Pat. No. 2,912,343, issued Nov. 10, 1959, the disclosure of which is incorporated herein by reference.
  • the emulsion layer resulting therefrom to contain variations in the ratio of silver halide to photographic image-forming coupler.
  • variations in the ratio of silver to image-forming coupler occur despite elaborate and sophisticated controls on the flow rates of the silver halide emulsion and the photographic imageforming coupler.
  • photographic image-forming coupler is used herein as a word of art and includes organic compounds which react with oxidized primary aromatic amine-developing agents to form dye images.
  • the photographic image-forming couplers, as well as the development inhibitor-releasing couplers which are utilized in the practice of this invention can embody any photographic coupler radical.
  • Typical useful photographic coupler radicals include the 5pyrazolone coupler radicals, the phenolic (including a-naphthol) coupler radicals, and the open-chain ketomethylene coupler radicals.
  • S-pyrazolone coupler radicals are customarily utilized for the formation of magenta dyes; phenolic coupler radicals are generally utilized for the formation of cyan color dyes; and, open-chain ketomethylene coupler radicals are generally utilized in the formation of yellow dyes.
  • the coupling position of such coupler radicals is also well known in the art.
  • the 5pyrazolone coupler radicals couple at the carbon atom in the 4-position thereof; the phenolic coupler radicals couple at the carbon atom in the 4-position (relative to the hydroxyl group); and, the open-chain ketomethylene coupler radicals couple at the carbon atom forming the methylene moiety (e.g.,
  • Formula I 0 be substituted); and, Y, can have a meaning given below for the image-forming and development inhibitor-releasing couplers utilized herein.
  • the image-forming and the development inhibitor-releasing couplers utilized in this invention can feature a 5-pyrazolone coupler radical having the following general formula:
  • R R and Y represent substituents of the type used in 5-pyrazolone couplers, for example, R can represent a value given for R R can represent a member selected from the group consisting of an alkyl group, a carbamyl group (which can be substituted), an amino group (which can be substituted with various groups such as one or two alkyl or aryl groups), an amido group, e.g., a benzamido group (which can be substituted), or an alkylamido group (which can besubstituted), and, Y can represent a value given below for the image forming and the development inhibitor-releasing couplers utilized herein.
  • photographic image-forming and development inhibitor-releasing couplers employed in the practice of this invention can utilize any suitable phenolic (including alphanaphtholic) coupler radicals, including those described in the structural formula below:
  • R R R R and Y can represent a substituent of the type used in phenolic couplers, for example, R and R each can represent a value given for R and in addition can represent a member selected from the group consisting of hydrogen, amino, carbonamido, sulfonamido, sulfamyl, carbamyl, halogen and alkoxy; R and R when taken together, can represent the carbon atoms necessary to complete a benzo group, which benzo group can be substituted with any of the groups given for R and R, and, when taken separately, R and R can each independently represent a value given for R and R and, Y represents a value given below for the imageforming and development inhibitor-releasing couplers utilized herein.
  • the image-forming couplers which can be utilized in the practice of this invention include the nondiffusible, openchain, S-pyrazolone and phenolic couplers referred to above, such as those couplers represented by Formula I, I] and ill above wherein Y, and Y each represents a group of the type used in colorless image forming couplers, such as hydrogen or a coupling off group, e.g., halogen, such as a chlorine or a fluorine atom; a thiocyano group; an acyloxy group, for example, an alkolyloxy group which can be substituted, or an aryloxy group which can be substituted, or a heterocycloyloxy group which can be substituted; a cyclooxy group including an aryloxy group, e.g., phenoxy, naphthoxy, or a heterocyclooxy group, such as a pyridinyloxy group, a tetrahydropyranyloxy group, a
  • the useful image-forming couplers include both the 4- equivalent and Z-equivalent nondiffusing couplers.
  • Typical useful 4-equivalent yellow dye-forming couplers which can be utilized in this invention include the following:
  • N-amyl-p benzoylacetaminobenzenesulfonate 2. N-(4-anisolyacetaminobenzenesulfonyl)-N-benzyl-mtoluidine 3. N-( 4-benzoylacetaminobenzenesulfonyl )-N-benzylaniline 4. m-(p-benzoylbenzoyl )acetaniiine 5. w-benzoyl-p-sec-amylacetaniline 6. N,N-di(m-benzoylacetyl )-p-phenylenediamine 7.
  • nonyl-p-benzoylacetaminobenzenesulfonate l l N-phenyl-N-(p-acetoacetaminophenyl)urea n-propyl-p-benzoylacetaminobenzenesulfonate acetoacetpiperidide l3.
  • the 2-equivalent yellow dye-forming couplers can be derived from corresponding parent 4-equivalent couplers by replacing one of the two hydrogens on the alpha-carbon (i.e., methylene) with any nonchromophoric coupling-oil group, in cluding coupling-off groups such as the al., atom, the chlorine atom, an acyloxy group, a cyclooxy group and a thiocyano group.
  • Typically useful Z-equivalent couplers include the alpha-fluoro couplers of US. Pat. No. 3,277,l55, the alpha chloro couplers of US. Pat. No.
  • Typical useful 2-equivalent yellow-forming openchain ketomethylene couplers include the following:
  • a-pivalyl-a-(4-sulfophenoxy-4-(N-methyl-N-octadecylsulfamyl)acetanilide potassium salt 14 a-[4-(4-hydroxyphenylsulfonyl)phenoxy]-a-pivaly
  • a-benzoyl-a-thiocyanoacetanilide Specific representative 4-equivalent magenta dye-forming couplers include can be used in this invention include the following:
  • the 2-equivalent S-pyrazolone couplers can be derived from the parent 4-equivalent S-pyrazolone couplers by replacing one of the hydrogens on the carbon in the 4-position of the pyrazolone ring with a nonchromophoric couplingoff group.
  • Examples of coupling-off groups which can be used in 2- equivalent magenta-forming S-pyrazolone couplers are the thiocyano group illustrated by the couplers in Loria U.S. Pat. No. 3,252,924 and the acyloxy group containing 2equivalent magenta-forming couplers of Loria U.S. Pat. No. 3,311,476.
  • Other useful coupling-off groups include acyloxy, aryloxy, alkoxy such as any of those shown in Whitmore et al., U.S. Pat. No. 3,227,550, the chlorine atom, the fluorine atom, and the sulfo group.
  • Typical 2equivalent magenta dye-forming couplers which can be used in this invention include the following:
  • 2-equivalent cyan-forming phenolic couplers can be used in the practice of this invention.
  • the 2-equivalent phenolic, couplers can be derived from the corresponding 4- equivalent phenolic couplers by substituting a nonchromophoric coupling-off group on the carbon in the 4- position of the phenolic or naphthoic ring.
  • the coupling-off groups include the acyloxy group illustrated by the 4-acyloxyphenols and 4acyloxynaphthols of Loria U.S. Pat. No. 3,31 1,476, issued Mar. 28, 1967, the cyclooxy group illustrated by the 4-cyclooxy naphthols of Loria U.S. patent application Ser. No. 483,807, filed Aug. 30, 1965, the thiocyano group illustrated by the 4-thiophenols and 4- thionaphthols of Loria U.S. Pat. No. 3,253,294, the cyclic imido groups as illustrated by the 4-cyclic imido derivatives of l-hydrogen-2-naphthamides of Loria U.S.
  • Typical 2-equivalent cyan-forming couplers which can be used in this invention include the following:
  • the concentration employed will depend on the characteristics of the dye formed by the coupler, and on the nature of the photographic emulsion in which it is incorporated.
  • the photographic image-forming coupler preferably is nondifi'usible, and colorless. It can be a coupler of the type which forms a diffusible dye image (which can be transferred to a suitable receiving sheet) or a type which forms nondiffusible dye images.
  • the invention is useful with all photographic incorporated image-forming couplers which form dye images by imagewise reaction with oxidized primary aromatic amine color-developing agent. Incorporated refers to silver halide emulsion layers containing photographic image-forming couplers at the time of exposure.
  • development inhibitor-releasing coupler is used herein as a word of art to refer to those photographic couplers which, upon reaction with oxidized primary aromatic amine color-developing agent, form dye and release a compound which inhibits development.
  • Development inhibitor-releasing (DlR) couplers which can be utilized herein can be represented by the general formula:
  • C represents a photographic coupler radical, preferably an open-chain ketomethylene, S-pyrazolone or phenolic (including alpha-naphtholic) coupler radicals, having said Z substituted in the coupling position of the coupler radical, Z representing an organic group which does not contain a chromophore, does not couple with oxidized primary aromatic amine color developer to form dye, does not inhibit development while attached to Cp, but is released from C on reaction with oxidized primary aromatic amine color develop ing agent, and either is or forms a compound which inhibits development.
  • Especially useful DIR couplers have formula I, ll or Ill above, wherein, Y Y and Y each are selected from:
  • a monothio group such as, ortho-nitro or ortho-amino substituted arylmonothio groups (such as, 2 -nitrophenyl and 2-aminophenyl), a carbon containing heterocyclic monothio group (generally having a 5 to 6-membered ring containing at least one heteronitrogen, oxygen or sulfur atom and preferably one to four heteronitrogen atoms) including heterocyclic radicals, such as, tetrazolyls, triazinyls, triazolyls, oxazolyls, oxadiazolyls, diazolyls, thiazyls, thiadiazolyls, benzoxazolyls, benzothiazolyls, pyrimidyls, pyridinyl, quinolinyls, etc., and in which the aryl-, heterocyclic moieties of the monothio group are either unsubstituted or substituted with various groups, such as nitro,
  • a 2-amidoarylazoxy group e.g., Z-acetamidophenylazoxy, 2-acetamido-4-rnethylphenylazoxy, 2-acetamido-4- chlorophenylazoxy, Z-palmitamidophenylazoxy, 4- methoxy-Z-palmitamidophenylazoxy, 4-chloro-2-pal mitamidopehnylazoxy, etc.
  • a Z-aryltriazolyl group e.g., 2-benzotriazolyl, 5-chloro-2- benzotriazolyl, 5-hydroxy-2-benzotriazolyl, 4,7-dinitro-2- benzotriazolyl, 5 -methyl-2-benzotriazolyl, 6-methoxy-2- benzotriazolyl, 4-carboxyethyl-4-sulfoethyl-2- benzotriazolyl, Z-naphthotriazolyl, 4-methyl-2 naphthotriazolyl, 5-chloro-Z-naphthotriazoyl 5-hydroxy- 2-naphthotriazolyl, 5-nitro-2 -naphthotriazolyl 5-sulfoethyl-2-naphthotriazolyl, 4-amino-2-naphthotriazolyl, benzo[ l,2-d:4,5-d]-bristriazolyl, etc.
  • the Z group (or Y Y and Y in the above formulas) l forms a diffusible mercaptan and (2), (3) and (4) form a diffusible aryltriazole upon reaction with oxidized color developing agent.
  • DIR couplers include the following:
  • Couplers 1 through 5, 11 through 27, 33 through 40 are described in Barr, U.S. Pat. No. 3,227,554.
  • Couplers 6, 7, 28 and 41 are prepared by methods similar to those disclosed in U.S. Pat. No. 3,148,06.
  • Couplers 8 through 10, 29 through 32 and 42 through 45 are described by Sawdey, U.S. Pat. application Ser. No. 674,090, filed Oct. 10, 1967.
  • the couplers referred to in the immediate paragraph are the DlR couplers listed above.
  • the most useful DIR couplers are those which have a monothio group in the coupling position (e.g., formula 1, II and 111 above in which Y,, Y and Y represent a monothio group).
  • Preferred DIR couplers have formula I, 11 or 111 above wherein Y Y and Y each represents a heterocyclic monothio radical in which the heterocyclic ring has from five to six atoms and at least one hetero atom selected from oxygen, sulfur and nitrogen, such as a hetero ring, containing from one to four hetero nitrogen atoms, e.g., a S-tetrazolylthio group.
  • a DIR coupler is selected which forms a dye of substantially the same color as the dye formed by the image-forming coupler.
  • the development inhibitor-releasing coupler is utilized at a concentration sufficient to effectively provide substantially uniform contrast in the emulsion layer.
  • concentration sufficient to effectively provide substantially uniform contrast in the emulsion layer.
  • the most useful concentration will depend upon how much variation there is in the ratio of silver halide to photographic image-forming coupler, as well as on the nature of the particular development inhibitor-releasing coupler selected. As a general guide, the most useful results are achieved using a ratio of from 2 to 25 parts by weight development inhibitor-releasing coupler per 100 parts by weight photographic image-forming coupler.
  • the photographic image-forming coupler and the development inhibitor-releasing coupler utilized in the photographic emulsions and processes of this invention preferably are nondiffusible.
  • nondiffusible as used herein has the meaning commonly applied to that term in color photography, and denotes materials which for all practical purposes do not migrate or wander through photographic hydrophilic colloid layers, such as gelatin, particularly during processing in aqueous alkaline solutions.
  • diffusible has the converse meaning.
  • the image-forming and the development inhibitor-releasing couplers utilized herein are ballasted. That is, the coupler contains an organic radical of such molecular size and configuration as to render the coupler nondiffusible in the element and when the element is processed in alkaline-developing solutions.
  • the organic ballasting radical is chosen so that it does not exercise any detrimental effects on the photographic material.
  • the image-forming and development inhibitor-releasing couplers utilized in this invention can be incorporated into the silver halide emulsion in any convenient manner.
  • the coupler can contain a solubilizing group, such as a sulfonic acid group or a carboxylic acid group, such the couplers soluble in alkaline solution.
  • a solubilizing group such as a sulfonic acid group or a carboxylic acid group
  • the couplers soluble in alkaline solution.
  • the couplers are incorporated into the emulsion by dissolving them in a suitable coupler solvent, for example, one of the color coupler solvents and utilizing one of the processes described in U.S. Pat. Nos. 2,322,027 and 2,801,171.
  • the photographic emulsions of this invention can contain a competing coupler, which can be introduced prior to coating the emulsion or during development thereof.
  • the competing coupler can be one which forms a leuco dye or a diffusible dye.
  • Typical useful competing couplers are described by Loria, Williams and Barr in British Pat. No. 1.038,33l; Wellar and Greet in U.S. Pat. No. 2,689,793, and U.S. Pat. No. 2,998,314.
  • Emulsion layers can be produced in accordance with this invention which contain colored couplers, e. g., those which contain an azo group in the coupling position.
  • couplers are well known in the photographic art.
  • Representative useful azo substituted couplers are described in the following U.S. Pat. Nos: 2,428,054, 2,449,966, 2,453,551 (open-chain ketomethylene couplers having an arylazo group in the coupling position; and couplers in which the arylazo group is replaced with an alkylazo or a heterocycloazo group in the coupling position are also useful); U.S. Pat. No.
  • blue radiation refers to radiation of from about 400 to 500 nm.
  • green refers to radiation of from about 500 to 600 nm.
  • red refers to radiation of from about 600 to 700 nm.
  • the cyan dyes formed by the colorless coupler has its major absorption between about 600 and 680 nm.; the magenta dye between about 500 and 580 nm.; and the yellow dye between about 400 and 480 nm.
  • a wide variety of organic hydrophilic-dispersing agents or substrates for the silver halide can be utilized.
  • Gelatin is preferred although other colloidal materials such as colloidal albumin, cellulose derivatives or synthetic resins such as polyvinyl alcohol can also be utilized.
  • silver halide emulsions can be coated on a wide variety of photographic supports.
  • Typical supports include cellulose nitrate film, cellulose acetate film, polyvinyl acetal film, polystyrene film, polyterephthalate film, polyethylene film,
  • polypropylene film polyethylene-coated paper, paper, glass and others.
  • the photographic silver halide emulsions and other layers on the present photographic elements can contain the addenda generally utilized in such elements including optical sensitizers, speed-increasing materials, antifoggants, coating aids, gelatin hardeners, plasticizers, ultraviolet absorbers and the like.
  • Coupler BA yellow dye-forming DIR-coupler of the type described in Weissberger et al. U.S. Pat. No. 3,265,506 Compound l3 Coupler CA magenta dyeforming coupler of the type described in Loria et al. US. Pat. No. 2,600,788 (Compound Coupler DA blue-absorbing magenta dye-forming coupler of the type described in Beavers U.S. Pat. No. 2,983,608 (Coupler l) Coupler EA magenta dye-forming DIR-coupler of the type described in Barr et al. US. Pat. No.
  • Coupler FA cyan dye-forming coupler of the type described in Weissberger et al. U.S. Pat. No. 2,474,293
  • Compound l Coupler G-A blue-green-absorbing cyan dye-forming coupler of the type described in Gledhill et al. U.S. Pat. No. 3,034,892
  • Coupler HA cyan dye-forming DIR-coupler of the type described in Barr et al. U.S. Pat. No.
  • Couplers are dissolved in organic solvents and dispersed in a gelatin solution as described in Fierke et al. U.S.
  • EXAMPLE 2 A photographic element of the type described above is prepared and coated in which the green-sensitive emulsion and the magenta dye-forming coupler dispersion are mixed just prior to coating as described in Collins et al. U.S. Pat. No.
  • a series of coatings are prepared in which the silver coverage/coupler coverage ratio is varied by varying the coupler dispersion flow rate and the nonDlR-coupler/DlR coupler ratio is varied by coating at a constant flow rate separate coupler dispersion having the appropriate ratios. Samples of each coating are exposed on an intensity scale sensitometer and processed through the Eastman Color Print Process, at 75 F. and a development time of 8 minutes with the following results.
  • said development inhibitor-releasing coupler has a monothio group in its coupling position which, upon reaction with oxidized primary aromatic amine color-developing agent, forms a diffusible mercaptan which inhibits development.
  • each of said couplers are selected from the group consisting of an open-chain ketomethylene coupler radical; a S-pyrazolone coupler radical; and, a phenolic coupler radical.
  • Coatings 4-8 demonstrate the good uniformity in contrast obtained in accordance with this invention.
  • each of said couplers has one of the following structural formulas:
  • EXAMPLE 3 Formula I 0 H
  • a photographic element of the type described above 15 R L prepared and coated in which the blue-sensitive emulsion and the yellow dye-forming coupler dispersion are mixed just prior 1 to coating as described in Collins et al. US. Pat. No. 2,912,343.
  • a series of coatings is prepared in which the silver coverage/coupler coverage ratio is varied by varying the coupler dispersion flow rate and the nonDlR-coupler/DlR-coupler ratio is varied by coating at a constant flow rate separate 1 n R coupler dispersion having the appropriate ratios.
  • Samples of Immula H T each coating were exposed on an intensity scale sensitometer Rs-N H l p and processed through the Eastman Co or rint Process, at cic F. and a development time of 8 minutes with the following ll results. 2
  • a method for avoiding substantial differences in image contrast within a photographic element said differences being attributable to uncontrolled variations in the ratio of incorporated image-forming coupler-to-silver halide in a photographic emulsion layer of said element, the improvement com prising introducing a development inhibitor-releasing coupler and at least one other coupler separately or in admixture at a controlled rate to effect an essentially constant ratio of development inhibitor-releasing coupler-toother coupler into a silver halide emulsion, admixing and coating the resulting composition onto a support.
  • a a member selected from the group consisting of hydrogen, halogen, a thiocyano group, an acyloxy group, an aryloxy group, a cyclooxy group, and, when said R and R represent the atoms to complete a benzo group, Y represents any of the foregoing groups given for Y and Y except aryloxy, and can in addition represent a cycloimido group, to complete said photographic image forming coupler; and,
  • a monothio group selected from an orthoamino substituted arylmonothio group; and, a heterocyclic radical containing at least one hetero atom selected from oxygen, sulfur and nitrogen, to complete said third coupler.

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US3839044A (en) * 1971-03-25 1974-10-01 Eastman Kodak Co Silver halide emulsions containing 2-equivalent color couplers
US3984245A (en) * 1973-10-09 1976-10-05 Fuji Photo Film Co., Ltd. Photographic sensitive materials
US3989529A (en) * 1974-10-29 1976-11-02 Gaf Corporation Hydrophilic coupler solutions
US4071365A (en) * 1975-09-16 1978-01-31 Mitsubishi Paper Mills, Ltd. Silver halide emulsion containing two-equivalent yellow dye-forming coupler
US4205990A (en) * 1975-08-02 1980-06-03 Konishiroku Photo Industry Co., Ltd. Process for forming a cyan dye image by the use of a 2-equivalent cyan coupler
US4226934A (en) * 1977-08-12 1980-10-07 Ciba-Geigy Ag Light sensitive photographic material containing development inhibitor releasing compounds
US4239851A (en) * 1978-02-02 1980-12-16 Fuji Photo Film Co., Ltd. Silver halide photographic light-sensitive material
US4286054A (en) * 1980-05-29 1981-08-25 Veb Filmfabrik Wolfen Light sensitive, color photographic silver halide compositions with DIR-couplers
US4315069A (en) * 1979-09-18 1982-02-09 Ciba Geigy Ag Color coupler combination
US4368255A (en) * 1980-07-16 1983-01-11 Ciba-Geigy Ag Method of processing monochrome silver halide material
US4387159A (en) * 1980-05-29 1983-06-07 Veb Filmfabrik Wolfen Light sensitive, color photographic silver halide compositions with DIR-couplers
EP0200206A2 (en) 1985-04-30 1986-11-05 Konica Corporation Silver halide photographic light-sensitive material

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JPS58217932A (ja) * 1982-06-11 1983-12-19 Fuji Photo Film Co Ltd ハロゲン化銀カラ−感光材料
FR3112334B1 (fr) 2020-07-10 2022-09-16 Ifollow Systemes de chargement et de déchargement de supports mobiles de collecte sur un robot autonome mobile pour la préparation de commande
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US2761791A (en) * 1955-02-23 1956-09-04 Eastman Kodak Co Method of multiple coating
US2912343A (en) * 1957-11-18 1959-11-10 Ilford Ltd Production of photographic material
US3148062A (en) * 1959-04-06 1964-09-08 Eastman Kodak Co Photographic elements and processes using splittable couplers

Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3839044A (en) * 1971-03-25 1974-10-01 Eastman Kodak Co Silver halide emulsions containing 2-equivalent color couplers
US3984245A (en) * 1973-10-09 1976-10-05 Fuji Photo Film Co., Ltd. Photographic sensitive materials
US3989529A (en) * 1974-10-29 1976-11-02 Gaf Corporation Hydrophilic coupler solutions
US4205990A (en) * 1975-08-02 1980-06-03 Konishiroku Photo Industry Co., Ltd. Process for forming a cyan dye image by the use of a 2-equivalent cyan coupler
US4071365A (en) * 1975-09-16 1978-01-31 Mitsubishi Paper Mills, Ltd. Silver halide emulsion containing two-equivalent yellow dye-forming coupler
US4226934A (en) * 1977-08-12 1980-10-07 Ciba-Geigy Ag Light sensitive photographic material containing development inhibitor releasing compounds
US4239851A (en) * 1978-02-02 1980-12-16 Fuji Photo Film Co., Ltd. Silver halide photographic light-sensitive material
US4315069A (en) * 1979-09-18 1982-02-09 Ciba Geigy Ag Color coupler combination
US4286054A (en) * 1980-05-29 1981-08-25 Veb Filmfabrik Wolfen Light sensitive, color photographic silver halide compositions with DIR-couplers
US4387159A (en) * 1980-05-29 1983-06-07 Veb Filmfabrik Wolfen Light sensitive, color photographic silver halide compositions with DIR-couplers
US4368255A (en) * 1980-07-16 1983-01-11 Ciba-Geigy Ag Method of processing monochrome silver halide material
EP0200206A2 (en) 1985-04-30 1986-11-05 Konica Corporation Silver halide photographic light-sensitive material
US4990437A (en) * 1985-04-30 1991-02-05 Konishiroku Photo Industry Co., Ltd. Silver halide photographic light-sensitive material

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Publication number Publication date
GB1269074A (en) 1972-03-29
BE730830A (enrdf_load_stackoverflow) 1969-09-01
FR2007360A1 (enrdf_load_stackoverflow) 1970-01-09

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