US2710801A - Non-diffusing polymeric reducing agents for photographic color emulsions - Google Patents

Non-diffusing polymeric reducing agents for photographic color emulsions Download PDF

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US2710801A
US2710801A US282490A US28249052A US2710801A US 2710801 A US2710801 A US 2710801A US 282490 A US282490 A US 282490A US 28249052 A US28249052 A US 28249052A US 2710801 A US2710801 A US 2710801A
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Prior art keywords
color
emulsion
stain
solution
diffusing
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US282490A
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English (en)
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Louis M Minsk
William O Kenyon
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Eastman Kodak Co
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Eastman Kodak Co
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Priority to BE549815D priority Critical patent/BE549815A/xx
Priority to BE519219D priority patent/BE519219A/xx
Priority to US282490A priority patent/US2710801A/en
Application filed by Eastman Kodak Co filed Critical Eastman Kodak Co
Priority to FR1098016D priority patent/FR1098016A/fr
Priority to GB10358/53A priority patent/GB738683A/en
Application granted granted Critical
Publication of US2710801A publication Critical patent/US2710801A/en
Priority to US525366A priority patent/US2816028A/en
Priority to FR1163009D priority patent/FR1163009A/fr
Priority to GB23400/56A priority patent/GB825421A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • 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
    • G03C7/392—Additives
    • G03C7/396—Macromolecular additives
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F16/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an alcohol, ether, aldehydo, ketonic, acetal or ketal radical
    • C08F16/02—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an alcohol, ether, aldehydo, ketonic, acetal or ketal radical by an alcohol radical
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F8/00—Chemical modification by after-treatment
    • 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
    • G03C1/04—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein with macromolecular additives; with layer-forming substances
    • 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
    • G03C1/04—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein with macromolecular additives; with layer-forming substances
    • G03C1/053—Polymers obtained by reactions involving only carbon-to-carbon unsaturated bonds, e.g. vinyl polymers

Definitions

  • This invention relates to color photography and particularly to a method for preventing the formation of color fog or stain in photographic emulsions.
  • color-forming or coupler compounds combine with the development product of aromatic amino photographic developers to produce dyes.
  • the color formers or couplers may be added directly to the emulsion layers or may be incorporated in the developing solution as described in Fischer U. S. Patent 1,102,028, granted June 30, 1914, or they may be incorporated in a waterper'meable medium which is insoluble in the carrier for the sensitive silver salt as described in Marines and Godowsky U. S. Patent 2,304,940, December 15, 1942, and Jelley and Vittum U. S. Patent 2,322,027 granted June 15, 1943. Y
  • a difficulty frequently encountered in these processes is the formation of color f'og or stain.
  • dye fog is frequently formed in the emulsion layer. This is because the developing agent has been oxidized to some extent by the action of the air and the oxidized developer tends .to couple with the color-forming compound at places in the photographic material where no silver image is produced. It is well known that in these processes the dye should be formed only where the silver halide is -reduced to metallic silver, thereby oxidizing the developing agent to a form which couples with the color former. Once the developing agent is oxidized, it couples immediately with the color former whether a photographic image is present or not.
  • a further object is to provide suitable non-diiiusing re- United States Patent-O the use of these simple reducing agents for preventing or ice ducing agents for incorporation in color photographic materials.
  • a further object is to provide a color forming photographicemulsion having non-diffusing couplers and non-diffusing stain or fog inhibitors incorporated therein.
  • Compounds having this structure include polyvinyl polymers comprising units such as the following: 1 -'cHr-cn- 0111+ on OH -OH HO HO Vinyl hydroquinonemethacrylic acid interpolymer 4 CH2-CH CH- coon dooH H 1 Vinyl hydroouinonemalelc acid inter-polymer 5 -GHCHCH -QH- "Vinyl bydroqiiii1one-pqne'thyl styrene inter-polymer- "vin y i byerif innbile:sa-uniretn i styrene nitrpoiimer' Vinyl hydroquinonevinyl naphthalene interpolymer 9 CH2CHCH2CH c o 0.11. -on
  • EXAMPLE 1 Polyvinyl gentisal Fifty-five and five-tenths grams of aqueous polyvinyl alcohol gel (17.28% solids) and 40.5 cc. of distilled water were heated on a steam bath with mechanical stirring in a three-necked flask equipped with stirrer, reflux condenser, and an inlet for dry nitrogen. Dry nitrogen was passed over the reaction mixture. When a smooth dope was obtained, 3 grams of gentisaldehyde followed by a solution of 12 cc. of concentrated hydrochloric acid diluted to cc. with distilled water, were added. Precipitation of a cake occurred. Heating and stirring under nitrogen was continued for 4 hours during which time redoping occurred to yield a smooth dope.
  • the dope was poured in a fine stream into 3 liters of absolute ethyl alcohol, and the fibrous precipitate was extracted with ethyl alcohol in a Soxhlet extractor for 44 hours.
  • the product was dried in a vacuum desiccator under constant water pump vacuum. Yield, 7 grams.
  • EXAMPLE 2 Polyacrylyl ascorbic acid Eight grams of polyacrylic anhydride were suspended in 100 ml. of dry pyridine. To this was added 0.86 cc. of distilled water, and the reaction mixture was refluxed for 20 minutes. Four grams of ascorbic acid were added and refluxing was continued for 30 minutes. A smooth dope, only slightly discolored, was obtained. Five cc. of distilled water were added and refluxing continued for another 3 minutes. The dope was poured into 1 liter of t-butyl alcohol and the precipitate obtained washed with fresh t-butyl alcohol.
  • the product was given three reprecipitations from pyridine (100 cc.) into t-butyl alcohol (1 liter), with additional washing with fresh t-butyl alcohol on the suction funnel after each precipitation. After the last precipitation, washing and filtering as dry as possible on the funnel, the solid was dispersed in 100 cc. of distilled water. The air above the dope was displaced by nitrogen, and the sample was stored in an ice chest until used.
  • EXAMPLE 4 Salt of ethylene diamine and 2,5-dihydrxy-p-benzene diacetic acid To a stirred solution of 9.0 g. (0.025 mole) of 2,5-dihydroxy-p-benzene diacetic acid in 400 cc. of absolute ethanol there was added slowly with stirring 2.6 g. (0.044 mole) of ethylene diamine dissolved in 200 cc. of absolute ethanol. The reaction mixture was then heated at 50 for one hour, cooled, and the salt filtered with suction. After drying at 60 in vacuo, it melted at 203 to 204. The yield was almost quantitative.
  • Polyamide from the salt of ethylene diamine and 2,5dihydraxy-p-benzenediacetic acid One gram of the salt of 2,5-dihydroxy-p-benzenediacetic acid with ethylene diamine was heated in a 20-mm. Pyrex test tube at 0.3 mm. at 190 to 195 until most of the white salt had fused hour). The reaction tube was cooled, the solid ground up, and extracted with water, and finally with alcohol. The purified solid was then dried in vacuo. Polyamides prepared in this manner at temperatures from 190-220 with reaction times from to 2 hours were insoluble in water, alcohol, and acetone, but soluble in dilute alkali.
  • EXAMPLE 5 Salt of ethylene glycol bisQS-aminoethyl) ether and 2,5-dihyar0xy-p-benzenediacetic acid
  • a solution of 13.0 g. (0.08 mole) of ethylene glycol bis (B-aminoethyl) ether and 300 cc. of absolute ethanol was added with stirring to a solution of 18.3 g. (0.081 mole) of 2,S-dihydroxy-p-benzenediacetic acid in 500 cc. of absolute alcohol and the mixture allowed to stand at 50 for one hour. salt filtered and dried in vacuo at 60, M. P. 217-218". The yield was 21 g. of salt (68 per cent yield). Additional salt was obtained from the mother liquors by evaporation.
  • our polymeric stain inhibitors may be either water-soluble or oil-soluble, and therefore may be incorporated either directly in a gelatin emulsion, or first incorporated in a water-insoluble solvent.
  • Water solubility is preferably, but not necessarily obtained by the presence of the saltforming -COOH groups included in the molecule; bases other than sodium hydroxide or other caustic alkali, for example, sodium carbonate or bicarbonate, may be used to effect solution.
  • Oil solubility is enhanced by having in the molecule, alkyl, aryl or ester groups.
  • EXAMPLE 6 Polyvinyl hydroquinone 2.56 g. of the magenta coupler 1-[4(2"-sulfobenzamido)phenyl]-3-stearamido-5-pyrazolone was dissolved in a mixture of 12 cc. of ethanol and 6 cc. of 20% aqueous sodium hydroxide. The solution was diluted with cc. of water and 2.5% citric acid solution added to bring the pH of the solution to 6.5, after which the volume of the neutralized solution was brought to 200 cc. To this solution was then added a solution of 0.16 g. of the antistain agent polyvinyl hydroquinone in 16 cc. of 50% ethanol. The resulting solution was mixed with 200 cc. of a melted silver halide gelatin emulsion and coated. This coating showed markedly lower stain densities than were obtained with a similar coating without the antistain agent.
  • acetaminobenzenesulfonyl) N('y-phenylpropyl)p toluidine and 0.2 gram of the polymeric anti-stain agent was dissolved in 15 cc. of di-n-butylphthalate by heating to C.
  • the hot solution was poured with stirring into a solution prepared by mixing 60 cc. of 10% gelatin, 25
  • the hot mixture was then passed several times through a colloid mill to obtain a uniform fine dispersion which was mixed with 150 cc. of a melted sensitive AgBr gelatin emulsion and coated on a transparent film support. After drying and exposure, color processing produced a bright yellow dye image which had distinctly lower yellow stain in the unexposed areas than was obtained with a similar coating from which the polymeric anti-stain agent was omitted.
  • EXAMPLE 9 Copolymer of vinyl hydroquinone and 3,4-dimelhyl styrene A solution was prepared by heating to C. a mixture of 6 grams of the coupler 3-(benzoylacetamino)3- (4-tert-amylphenoxy) benzanilide, 0.6 gram of the polymeric anti-stain agent and 15 cc. of quinitol di-Z-ethylhexoate. The hot solution was poured with stirring into 150 cc. of an aqueous solution containing 8 grams of gelatin and 0.8 gram of Alkanol B. The mixture was passed several times through a colloid mill and then added to 140 cc.
  • EXAMPLE 10 Copolymer of vinyl hydroquinone and butyl methacrylate
  • a solution of 4.6 grams of the coupler Z-(diamylphenoxyacetamino)-4,6-dichloro-S-methylphenol and 0.65 gram of the polymeric anti-stain agent in 10 cc. of di-nbutylphthalate was prepared by heating a mixture of the components to 150 C. The hot solution was poured with stirring into 160 cc. of an aqueous solution of 5.5 grams of gelatin and 0.7 gram of Alkanol B. The resulting mixture was recycled through a colloid mill for five minutes, and the resulting fine dispersion was mixed v with 140 cc. of a melted sensitive AgBr gelatin emulsion.
  • EXAMPLE 12 Polyvinyl gentisal A mixture of grams of the coupler l-hydroxy-2- [a-(2,4-diamylphenoxy)-n-butyl]-naphthamide and 0.5 gram of the polymeric anti-stain agent was dissolved in 30 cc. of tri-cresylphosphate by heating to 140 C. The hot solution was poured with stirring into a solution prepared by mixing 115 cc. of 10% gelatin, 35 cc. of 5% Alkanol B and 200 cc. of water. The whole mixture was then passed several times through a colloid mill. The resulting fine dispersion was mixed with 315 cc. of a melted sensitive AgBr gelatin emulsion and coated.
  • EXAMPLE l3 Condensation product of gentisaldehyde and the copolymer of amino styrene and maleic acid 3.2 grams of the coupler l-[4'-(2-sulfobenzamido)- phenyl]-3-stearamidmS-pyrazolone was dissolved in a mixture of 15 cc. of ethyl alcohol and 7.5 cc. of NaOH. The resulting solution was diluted with 200 cc. of water and the pH adjusted to 6.5 by the addition of 5% citric acid solution. This solution was then mixed with 250 cc.
  • EXAMPLE 14 Polyamide from ethylene glycol bis-(fl-amirzoethyl) ether and 2,5-dihydr0xy-p-benzene diacetic acid 20 grams of the coupler 1-phenyl-3- ⁇ 3'-[2"-(2"',4'- di-tert. amylphenoxy)-5"-(3", 5"-dicarbornethoxyphenylcarbamylvaleramido) benzamido]-benzamido ⁇ -5- pyrazolone was dissolved in a mixture of cc. of ethyl alcohol and 45 cc. of 25% NaOH. This solution was diluted to 600 cc.
  • EXAMPLE 15 Condensation product of gentisaldehyde and the copolymat of aminostyrene and maleic acidc0upler in solvent dispersion
  • Five grams of the coupler Z-(diamylphenoxyacetamino)-4,6-dichloro-S-methylphenol was dissolved in 15 grams of di-n-butylphthalate by heating to 150 C.
  • the hot solution was poured with stirring into cc. of an aqueous solution of 5 grams of gelatin and 0.7 gram of Alkanol B.
  • the resulting mixture was passed five times through a colloid mill, then mixed with 50 cc.
  • Our compounds are employed in amounts of from 0.5% to 20% of the amount of coupler used in the emulsion although more or less of the non-diffusing stain inhibitors may be employed.
  • Vehicles other than gelatin may be used in our emulsions, e. g., polyvinyl alcohol, casein and its derivatives, gelatin derivatives, water-permeable cellulose derivatives, polyacrylamides and polyvinyl acetals, or mixtures of these with gelatin.
  • Our agents can be used in single layer or multi-laycr emulsion coatings or in mixed grain systems of the type described in Mannes and Godowsky U. S. Patent 2,388,859 and Fierke and Chechak U. S. Patent 2,490,749.
  • Our stain inhibitors are particularly useful with paper materials where it is important to reduce the minimum or fog densities. This applied both to negative developing paper and to reversal paper. Our stain inhibitors may, of course, also be used with transparency materials.
  • a color-forming photographic emulsion having reduced fogging tendency comprising a silver halide emulsion having incorporated therein a non-diifusing color coupler and, as an inhibitor of color stain, a non-diffusing polymeric compound having as part of its molecule recurring units containing at least two hydroxyl groups, two of which hydroxyl groups are part of the structure:
  • a color-forming photographic emulsion having reduced fogging tendency comprising a silver halide emulsion having incorporated therein a non-difiusing color coupler and, as an inhibitor of color stain, a non-diffusing polymeric compound comprising a polymeric hydrocarbon chain having attached thereto recurring units containing two or more hydroxyl groups, two of which groups are part of the structure:
  • a color-forming photographic emulsion having reduced fogging tendency comprising a silver halide emulsion having incorporated therein a non-diffusing color coupler and as an inhibitor of color stain, a non-dilfusing polyvinyl hydroquinone.
  • a color-forming photographic emulsion having reduced fogging tendency comprising a silver halide emulsion having incorporated therein a non-difiusing color coupler and as an inhibitor of color stain, a non-diffusing copolymer of vinyl hydroquinone and styrene.
  • a color-forming photographic emulsion having reduced fogging tendency comprising a silver halide emulsion having incorporated therein a non-diffusing color coupler and as an inhibitor of color stain, a non-diffusing polyvinyl gentisal.
  • a color-forming photographic emulsion having reduced fogging tendency comprising a silver halide emulsion having incorporated therein a non-diifusing color coupler and as an inhibitor of color stain, a non-diffusing polyacrylyl ascorbic acid.
  • a color-forming photographic emulsion having reduced fogging tendency comprising a silver halide emu1- sion having incorporated therein a non-diffusing color coupler and as an inhibitor of color stain, a non-diffusing polymer containing hydroquinone units.
  • a color-forming photographic emulsion having reduced fogging tendency comprising a silver halide emulsion having incorporated therein a non-difiusing color coupler and as an inhibitor of color stain, a non-diffusing interpolymer of vinyl hydroquinone and another polymerizable compound.

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  • Chemical & Material Sciences (AREA)
  • Physics & Mathematics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • General Chemical & Material Sciences (AREA)
  • Silver Salt Photography Or Processing Solution Therefor (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
US282490A 1952-04-15 1952-04-15 Non-diffusing polymeric reducing agents for photographic color emulsions Expired - Lifetime US2710801A (en)

Priority Applications (8)

Application Number Priority Date Filing Date Title
BE549815D BE549815A (d) 1952-04-15
BE519219D BE519219A (d) 1952-04-15
US282490A US2710801A (en) 1952-04-15 1952-04-15 Non-diffusing polymeric reducing agents for photographic color emulsions
GB10358/53A GB738683A (en) 1952-04-15 1953-04-15 Improvements in colour photography
FR1098016D FR1098016A (fr) 1952-04-15 1953-04-15 Perfectionnements à la photographie en couleurs
US525366A US2816028A (en) 1952-04-15 1955-07-29 Polymeric gentisamide antistain agents for color photography
FR1163009D FR1163009A (fr) 1952-04-15 1956-07-28 Nouvelle émulsion photosensible pour la photographie en couleurs et produits photographiques comprenant une telle émulsion
GB23400/56A GB825421A (en) 1952-04-15 1956-07-30 Improved antistain agents for colour photography

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US282490A US2710801A (en) 1952-04-15 1952-04-15 Non-diffusing polymeric reducing agents for photographic color emulsions
US525366A US2816028A (en) 1952-04-15 1955-07-29 Polymeric gentisamide antistain agents for color photography

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US525366A Expired - Lifetime US2816028A (en) 1952-04-15 1955-07-29 Polymeric gentisamide antistain agents for color photography

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Cited By (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2931271A (en) * 1955-08-03 1960-04-05 Polaroid Corp Sheet stock for dichroic dye light-polarizing means and process of preparation
US2933474A (en) * 1958-10-02 1960-04-19 Du Pont Vinyl or allyl salicylate-ethylene copolymers and chelates thereof
US3186970A (en) * 1961-07-31 1965-06-01 Polaroid Corp Preparation of polyhydroxyaryl partial acetals of polyvinyl alcohol
US3267073A (en) * 1962-09-04 1966-08-16 Rohm & Haas Hydrophilic redox vinyl polymers containing quinone groups
US3459548A (en) * 1967-07-24 1969-08-05 Polaroid Corp Scavengers for oxidized developing agent
US3996160A (en) * 1975-02-24 1976-12-07 Dynapol Corporation Hydroquinonoid ortho-alkylation polymers and the process of their production
US4065435A (en) * 1973-12-21 1977-12-27 Fuji Photo Film Co., Ltd. Water-soluble polymers and process for producing the same
DE3126322A1 (de) * 1980-07-04 1982-05-06 Fuji Photo Film Co., Ltd., Minami-Ashigara, Kanagawa Farbphotographisches empfindliches material
DE3142592A1 (de) * 1980-10-27 1982-07-15 Fuji Photo Film Co., Ltd., Minami-Ashigara, Kanagawa Farbphotographisches, lichtempfindliches silberhalogenidelement
US4412050A (en) * 1981-01-05 1983-10-25 Polaroid Corporation Linear polymers from blocked vinyl biphenyl compounds
EP0147854A2 (en) 1983-12-29 1985-07-10 Fuji Photo Film Co., Ltd. Silver halide photographic light-sensitive materials
EP0209118A2 (en) 1985-07-17 1987-01-21 Konica Corporation Silver halide photographic material
US4983506A (en) * 1987-10-14 1991-01-08 Fuji Photo Film Co., Ltd. Silver halide photographic material
USH1092H (en) 1989-06-08 1992-08-04 Akira Kobayashi Silver halide photographic light-sensitive material
EP0532192A1 (en) * 1991-09-12 1993-03-17 Minnesota Mining And Manufacturing Company Silver halide imaging materials
US5434041A (en) * 1993-04-02 1995-07-18 Eastman Kodak Company Photographic elements containing particular color couplers in combination with hydroquinone type stabilizers
EP0800113A2 (en) 1996-04-05 1997-10-08 Fuji Photo Film Co., Ltd. Silver halide color photographic light-sensitive material
US6479198B2 (en) * 2000-02-01 2002-11-12 Fuji Photo Film Co., Ltd. Silver halide light-sensitive material containing tanning developing agent

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4264766A (en) * 1877-09-19 1981-04-28 Hoffmann-La Roche Inc. Immunological diagnostic reagents
US4366238A (en) * 1981-06-25 1982-12-28 Fuji Photo Film Co., Ltd. Silver halide photographic materials
DE4338105A1 (de) * 1993-11-08 1995-05-11 Agfa Gevaert Ag Farbfotografisches Aufzeichnungsmaterial
JP3468432B2 (ja) * 1994-08-17 2003-11-17 富士写真フイルム株式会社 ハロゲン化銀写真感光材料
US5871894A (en) * 1995-10-16 1999-02-16 Fuji Photo Film Co., Ltd. Silver halide color photographic light-sensitive material

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2268630A (en) * 1937-01-21 1942-01-06 Gen Aniline & Film Corp Color photography
US2360290A (en) * 1941-07-31 1944-10-10 Eastman Kodak Co Preventing formation of color fog in emulsions
US2418613A (en) * 1945-07-30 1947-04-08 Eastman Kodak Co Fog inhibitors for photographic emulsions

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2268630A (en) * 1937-01-21 1942-01-06 Gen Aniline & Film Corp Color photography
US2360290A (en) * 1941-07-31 1944-10-10 Eastman Kodak Co Preventing formation of color fog in emulsions
US2418613A (en) * 1945-07-30 1947-04-08 Eastman Kodak Co Fog inhibitors for photographic emulsions

Cited By (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2931271A (en) * 1955-08-03 1960-04-05 Polaroid Corp Sheet stock for dichroic dye light-polarizing means and process of preparation
US2933474A (en) * 1958-10-02 1960-04-19 Du Pont Vinyl or allyl salicylate-ethylene copolymers and chelates thereof
US3186970A (en) * 1961-07-31 1965-06-01 Polaroid Corp Preparation of polyhydroxyaryl partial acetals of polyvinyl alcohol
US3267073A (en) * 1962-09-04 1966-08-16 Rohm & Haas Hydrophilic redox vinyl polymers containing quinone groups
US3459548A (en) * 1967-07-24 1969-08-05 Polaroid Corp Scavengers for oxidized developing agent
US4065435A (en) * 1973-12-21 1977-12-27 Fuji Photo Film Co., Ltd. Water-soluble polymers and process for producing the same
US3996160A (en) * 1975-02-24 1976-12-07 Dynapol Corporation Hydroquinonoid ortho-alkylation polymers and the process of their production
US4345016A (en) * 1980-07-04 1982-08-17 Fuji Photo Film Co., Ltd. Color photographic sensitive material
DE3126322A1 (de) * 1980-07-04 1982-05-06 Fuji Photo Film Co., Ltd., Minami-Ashigara, Kanagawa Farbphotographisches empfindliches material
US4358534A (en) * 1980-10-27 1982-11-09 Fuji Photo Film Co., Ltd. Silver halide color photographic light-sensitive element
DE3142592A1 (de) * 1980-10-27 1982-07-15 Fuji Photo Film Co., Ltd., Minami-Ashigara, Kanagawa Farbphotographisches, lichtempfindliches silberhalogenidelement
US4412050A (en) * 1981-01-05 1983-10-25 Polaroid Corporation Linear polymers from blocked vinyl biphenyl compounds
EP0147854A2 (en) 1983-12-29 1985-07-10 Fuji Photo Film Co., Ltd. Silver halide photographic light-sensitive materials
EP0209118A2 (en) 1985-07-17 1987-01-21 Konica Corporation Silver halide photographic material
US4983506A (en) * 1987-10-14 1991-01-08 Fuji Photo Film Co., Ltd. Silver halide photographic material
USH1092H (en) 1989-06-08 1992-08-04 Akira Kobayashi Silver halide photographic light-sensitive material
EP0532192A1 (en) * 1991-09-12 1993-03-17 Minnesota Mining And Manufacturing Company Silver halide imaging materials
US5800974A (en) * 1991-09-12 1998-09-01 Imation Corp. Silver halide imaging materials
US5434041A (en) * 1993-04-02 1995-07-18 Eastman Kodak Company Photographic elements containing particular color couplers in combination with hydroquinone type stabilizers
EP0800113A2 (en) 1996-04-05 1997-10-08 Fuji Photo Film Co., Ltd. Silver halide color photographic light-sensitive material
US6479198B2 (en) * 2000-02-01 2002-11-12 Fuji Photo Film Co., Ltd. Silver halide light-sensitive material containing tanning developing agent

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GB738683A (en) 1955-10-19
BE519219A (d)
FR1163009A (fr) 1958-09-22
FR1098016A (fr) 1955-07-15
US2816028A (en) 1957-12-10
BE549815A (d)
GB825421A (en) 1959-12-16

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