US2698797A - Mixed packet photographic emulsions using resin couplers - Google Patents

Mixed packet photographic emulsions using resin couplers Download PDF

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Publication number
US2698797A
US2698797A US345626A US34562653A US2698797A US 2698797 A US2698797 A US 2698797A US 345626 A US345626 A US 345626A US 34562653 A US34562653 A US 34562653A US 2698797 A US2698797 A US 2698797A
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resin
coupler
emulsion
solution
gelatin
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Godowsky Leopold
Louis M Minsk
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Eastman Kodak Co
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Eastman Kodak Co
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Priority to GB8535/54A priority patent/GB767028A/en
Priority to DEE8779A priority patent/DE1009023B/de
Priority to FR1105868D priority patent/FR1105868A/fr
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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
    • G03C7/388—Processes for the incorporation in the emulsion of substances liberating photographically active agents or colour-coupling substances; Solvents therefor
    • G03C7/3882—Processes for the incorporation in the emulsion of substances liberating photographically active agents or colour-coupling substances; Solvents therefor characterised by the use of a specific polymer or latex
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
    • G03C7/00—Multicolour photographic processes or agents therefor; Regeneration of such processing agents; Photosensitive materials for multicolour processes
    • G03C7/30—Colour processes using colour-coupling substances; Materials therefor; Preparing or processing such materials
    • G03C7/32—Colour coupling substances
    • G03C7/327—Macromolecular coupling substances
    • G03C7/3275—Polymers obtained by reactions involving only carbon-to-carbon unsaturated bonds, e.g. vinyl polymers

Definitions

  • This invention relates to color photography and particularly to mixed packet photographic emulsions.
  • mixed grain photographic emulsions that is, photographic systems in which differently sensitized silver halide grains are incorporated in a single photographic emulsion layer and used to produce differently colored photographic images in the layer.
  • Mixed grain systems have a number of advantages, chief among which is the simplicity of coating a single emulsion layer rather than several layers. Other advantages are the improved definition obtained by having the differently sensitized particles juxtaposed in a single layer, and the simplification of processing which is generally obtained.
  • the system described in the Godowsky application requires a separate packet former and coupler; this is sometimes a disadvantage.
  • the resin couplers wh ch we propose to use havethe following recurring structure:
  • R is hydrogen or a phenyl, alkyl, alkoxy, car boxyalkyl or acyloxy radical, x and y are 0 or 1
  • R represents a color-forming group capable of reacting with the oxidation product of a primary aromatic amino developing agent on photographic development
  • R" is hydrogen or an alkyl radical, e. g., methyl or ethyl, said color-forming material containing an aryl group.
  • a solution of the sodium salt or other water-soluble salt of the resin-coupler 1s preferably first added to the silver halide emulsion, preferably a gelatino-silver chlorobromide emulsion, as shown in the three boxes at the top of the drawing and packets or discrete particles of emulsion and resin-coupler formed by adding to the combination of emulsion and resincoupler either (1) a water-soluble polymer or watersoluble salt of a polymer containing salt-forming acid groups, e. g. methyl-u-methacrylate-methacrylic acid, as shown in the left column of the drawing or (2) a solution of a precipitant for the resin coupler, preferably an alkaline earth metal salt, e. g. calcium acetate, as shown in the right column of the drawing.
  • a precipitant for the resin coupler preferably an alkaline earth metal salt, e. g. calcium acetate
  • the formation of packets is brought about by adding to the solution of silver halide emulsion and resin-coupler, a water solution of a watersoluble polymer or a water-soluble salt of a polymeric material containing salt-forming acid groups, such as the copolymer of methacrylic acid and methyl-a-methacrylate (Minsk, Weyerts and McDowell U. S. Patent 2,391,181), algin (alkali metal salt of polymeric-dmannuronic acid), carboxymethyl cellulose (Collins, Freeman and Anthonisen U. S. Patent 2,278,612), and cellulose sulfate (Belgian Patent 448,249), or the resincoupler may be added to a solution of the emulsion and water-soluble polymer or salt of the polymer.
  • a water solution of a watersoluble polymer or a water-soluble salt of a polymeric material containing salt-forming acid groups such as the copolymer of methacrylic acid and
  • the solution of silver halide emulsion and resin coupler and a solution of a polyvalent metal salt, a polyamine, a high molecular weight amine, or a high molecular weight quaternary salt, especially a solution of an alkaline earth metal salt, e. g., calcium, strontium or magnesium, are added slowly and simultaneously to a second solution of the alkaline earth metal salt.
  • the alkaline earth metal ion forms a salt with the acid group of the resin coupler, and packets or particles of resin-coupler salt, gelatin and silver halide are formed. Additional gelatin is ordinarily added to complete the emulsion or dispersion of sensitive color-forming particles.
  • Example 1 To 4.4 g. of a red-sensitive silver chlorobromide emulsion containing 80% by Weight silver chloride and having a gelatin content of 21.6 g. per mol of silver, there was added 44 cc. of water and the mixture stirred for 10 minutes at 40 C. To this emulsion, there was added 14 cc. of a 5% solution in water of the sodium s lt of the resin cou ler of Example 7 (pH about 7). This mixture was stirred for 20 minutes and 3 cc. of a -10% solution of the copolymer of methvl-a-methacrylate and methacrylic acid was added at pH 8. The solution was mixed for 25 minutes and 6 cc. of 10% magnesium sulfate solution was added to the mixture, stirred for 5 minutes more, and 25 cc. of 20% gelatin solution added.
  • Example 2 To 3.2 g. of a silver chlorobromide emulsion containing 2% by weight silver chloride and having a gelatin content of 21.0 g. per mol of silver, there was added 22 cc.
  • Example 3 To 4 g. of a green-sensitive gelatino-silver chlorobromide emulsion containing by weight silver chloride and having 8.7 g. of gelatin per mol of silver. there 9 was added 40 cc. of water and 3.3 g. of 20% phthalic anhydride gelatin (prepared by reacting 20 g. of phthalic anhydride with 100 g. of gelatin in the manner described in Example 1 of Yutzy and Frame U. S. Patent 2,525,753). To this emulsion there was added 7 cc. of a solution in water of the sodium salt of the resin coupler of Example 9. After stirring for 20 minutes, 2 cc.
  • a mixed packet emulsion of two colors was made as follows:
  • Example 4 To 1 part of the emulsion of Example 2, there were added 2 parts of the emulsion of Example 1 with addition of the usual spreading agent and emulsion hardener. This mixed emulsion was coated on 5 x 7 glass plates, exposed under a step tablet and processed in a developing solution of the following composition to form a negative colored image.
  • a mixed packet emulsion may also be made using the resin couplers of our invention, by precipitating the resin coupler and silver halide gelatin packet with heavy metal salt, without using the water-soluble polymers, such as methyl-u-methacrylate and methacrylic acid copolymer. This is illustrated by the following examples:
  • Example 5 To 30 cc. of a 4% solution of resin coupler prepared by the reaction of vinyl acetate-maleic anhydride interpolymer and 1-hydroxy-4-cl1loro-2- ⁇ 3-aminoethyl naphthamide as described in Example 12, there was added sulficient dilute acetic acid to adjust the pH to 7 to 7.5. To this solution, there was added with stirring at 40 C., 3.5 g. of a red-sensitive gelatino-silver chlorobromide emulsion containing an 80% by weight silver chloride. This solution of silver halide emulsion and coupler, and 32 cc. of a 1% solution of calcium acetate were added slowly and simultaneously to 56 cc. of a 0.1% solution of calcium acetate over a period of /2 hour. Packets of emulsion and coupler formed during this addition, the
  • Example 6 A dispersion of a green-sensitive magenta-forming emulsion was formed similarly to Example 5, using as the resin coupler, 15 cc. of a 4% solution of a resin coupler prepared from styrene-maleic anhydride interpolymer and l-p-aminophenol-3-butyramido-5-benzoxypyrazole as described in Example 14, and 2 g. of a green-sensitive gelatino-silver chlorobromide emulsion containing 80% by weight silver chloride. This solution and 16 cc. of a 2% solution of calcium acetate were added slowly and with stirring to 28 cc. of a 0.2% solution of calcium acetate to form the green-sensitive packet emulsion.
  • a mixed emulsion 7.5 g. of each of the redsensitive and green-sensitive emulsions were mixed with 7.5 g. of 10% bone gelatin solution to which was added a dioctyl hydroquinone dispersion equal to 100 mg. of dioctyl hydroquinone.
  • the mixed emulsion was coated at a rate of 12 cc. per 5 x 7 inch plate, dried, exposed through a color test chart, developed with the developing solution of Example 4, bleached and fixed in the usual manner.
  • the packet emulsion may be used as a single layer emulsion on the usual photographic support, or one or more packet emulsions may be used as one of the layers of a multilayer photographic coating, for example, in a multilayer photographic material having superposed red-sensitive, green-sensitive and blue-sensitive silver halide emulsions.
  • the resin couplers which we use may also be incorporated directly in a silver halide emulsion without the 4 formation of packets, in the manner suggested by Fisher U. S. Patent 1,102,028.
  • Typical polymers which may be used in forming the resin couplers used according to our invention, and methods by which the polymers may be prepared, are as follows:
  • 292 g. of acrylic anhydride 2920 cc. of dry 1,4 dioxane, and 1.46 g. of benzoyl peroxide.
  • the reaction mixture was heated on a steam bath for four hours during which time it turned to a white thick slurry.
  • the precipitate was filtered on to a Buchner funnel, washed quickly with 1,4 dioxane and dried over calcium chloride in a vacuum desiccator under a constantly applied vacuum.
  • the resin couplers which we use are made by reacting these or similar polymers with couplers containing an amino radical.
  • the preparation of suitable polymeric couplers is described below.
  • resin couplers capable of forming cyan dye images on color development may be prepared from 2- aminophenol and polyacrylic anhydride, 2-aminophenol and styrene-maleic anhydride polymers, 2-amino-4,6- dichloro-S-methyl phenol and styrene-maleic anhydride interpolymers, and S-amino-l-naphthol and vinyl acetateialeic anhydride interpolymers.
  • Example 8 Polymeric coupler having the recurring structure
  • Two hundred grams of p-aminoa-benzoylacetanilide, washed in by 100 cc. of dry acetone were added and the reaction mixture heated on a steam bath for one hour with stirring, after which time a second viscous phase had separated.
  • the reaction mixture was poured into 16 liters of distilled water containing 500 cc. of concentrated hydrochloric acid, with vigorous stirring and the gummy precipitate was stirred until it had turned friable.
  • the product was filtered onto a Buchner funnel, Washed with water and given two reprecitations from acetone into 16 liters of distilled water containing 500 cc. of concentrated hydrochloric acid. After the second precipitation, it was washed chloride free and dried over r night in a vacuum desiccator over calcium chloride with constant Water pump vacuum. The product was dissolved in 900 cc. of acetone boiled with 150 grams of decolorizing carbon (Norite) and filtered. The filtrate was diluted with 9:1 acetone-distilled water (400 cc.
  • the precipitate was redissolved in 3 liters of distilled water by the addition of 10% aqueous sodium hydroxide, with stirring. Precipitation was then caused by acidification to Congo red with concentrated hydrochloric acid. The precipitate was filtered as above and washed until the filtrate was free from chloride. Resolution in dilute sodium hydroxide and reprecitation as above was repeated again washing until the filtrate Was chloride free. The product was then dried in a desiccator over calcium chloride with constant water pump vacuum. Yield: 58 grams.
  • Example 10 Polymeric coupler having the recurring structure
  • a 3-necked flask equipped with a nitrogen inlet, a mechanical stirrer, and a reflux condenser protected from moisture by a calcium chloride tube, were placed 6.3 g. of polyacrylic anhydride, 20 g. of 2-amino-4,6- dichloro-5-methylphenol, and 100 cc. of dry acetone.
  • the reaction mixture was heated on a steam bath with stirring while the air in the flask was displaced by dry nitrogen. In a short time an orange-brown dope was obtained. After one hour of heating, the dope was poured in a fine stream into 2 liters of distilled water containing cc. of concentrated hydrochloric acid.
  • the friable precipitate obtained was Washed with distilled water and reprecipitated twice from 150 cc. of acetone into 2 liters of distilled water containing 50 cc. of concentrated hydrochloric acid. It was then washed free from chloride with distilled water and dried in a vacuum desiccator under constant water pump vacuum. The yield was 11.2 g.
  • Example 1 Polymeric coupler having the recurring structure OH OH1CHOHCH 1 (1.10 JJONH- Twenty grams of styrene-maleic anhydride interpolymer were dispersed under dry nitrogen in 200 cc. of dry acetone in a three-necked flask equipped with a mechanical stirrer, reflux condenser protected from moisture by a calcium chloride tube, and a nitrogen inlet. To the dope was added 25 g. of o-aminophenol. The reaction was heated on a steam bath under dry nitrogen. After twenty minutes, 100 cc.
  • Example 12 Polymeric coupler having the recurring structure 30 ('JONHCHzCHzNHC ln a 3-necked flask equipped with a reflux condenser protected from moisture by a calcium chloride tube and a mechanical stirrer, 322 g. of vinyl acetate-maleic anhydride interpolymer were dispersed in 2100 cc. of dry acetone. When doping was complete, 470 g. of l-hydroxy-4-chloro-2(fi-aminoethyl)naphthamide were added followed by 1120 cc. of dry acetone and 150 cc. of dry pyridine. The reaction mixture was heated with stirring on a steam bath. In 5 minutes it grew cloudy.
  • Example 13 Polymeric coupler having the recurring structure CH:CHCHCH
  • a styrene-malcic anhydride interpolymer were dispersed in 1600 cc. of dry acetone in an all-glass reflux outfit equipped with a mechanical stirrer and a reflux condenser protected from moisture by a calcium chloride tube.
  • To the dope was added 220 g. of benzoylaceto-p-aminoanilide followed by 400 cc. of dry pyridine.
  • the smooth dope obtained was heated on a steam bath with stirring for two hours during which time a soft second phase appeared.
  • One hundred cc. of distilled water were added and with continued stirring a smooth dope was again obtained.
  • the product was dried in the air to remove ether and twice slurried for twenty minutes with 8-liter portions of distilled water, each containing 200 cc. of concentrated hydrochloric acid, filtering by suction after each and washing on the funnel with distilled water.
  • the product was stirred for 10 minutes with 8 liters of distilled water, filtered, further washed on the funnel with distilled water, and dried at 40 C. in an air oven.
  • the yield was 173 g. containing 8.35% of nitrogen.
  • This polymer coupler dissolve with warming in diluted potassium carbonate solution during which time the benzoxyl group hydrolyzes off.
  • resin couplers capable of forming a magenta image upon coupling are the pyrazolyl styrene-maleic acid interpolymers described in Laakso and Allen U. S. Patent 2,646,421.
  • a light-sensitive photographic emulsion comprising a mixture of hydrophilic, water-permeable colloid, silver halide sensitive to at least one region but less than all re ions of the visible spectrum, and a water-insoluble nondilfusing resin-coupler compound selected from those compounds having the recurring structure where R is selected from the class consisting of hydrogen, phenyl, alkyl, alkoxy, carboxyalkyl and acyloxy radicals, x and y are selected from the class consisting of 0 and l, R represents a color-forming group including an aryl group, capable of reacting with the oxidation product of a primary aromatic amino developing agent on photographic development, and R is selected from the class consisting of hydrogen and an alkyl radical, and the waterinsoluble salts of said compounds, and at least one separate mixture of hydrophilic water-permeable colloid.
  • silver halide sensitive to a region of the visible spectrum different from that to which said first-mentioned silver halide is sensitive, and non-diffusing resin coupler having the formula stated above but having a color-forming group differing in chemical structure from said first-mentioned color-forming group and yielding a different dve with said developing agent.
  • a light-sensitive mixed packet photographic emulsion comprising packets or discrete particles of gelatin, silver halide sensitive to at least one region but less than all regions of the visible spectrum, and a salt of a nondiffusing resin-coupler compound of the recurring structure to ()H ins-R where R represents an o-hydroxy-substituted phenyl radical, and a separate setof packets or discrete particles of gelatin, silver halide sensitive to a region of the visible spectrum dilferent from that to which said first-mentioned silver halide is sensitive, and a salt of a non-difi'using resin coupler having the composition $11 ATH-QNHR where R represents the residue of a benzoylacetyl group.
  • R is selected from the class consisting of phenyl, carboxyalkyl and acyloxy radicals, x and y are selected from the class consisting of 0 and l, R represents a colorforming group including an aryl group, capable of reacting with the oxidation product of a primary aromatic amino developing agent, and R is selected from the class consisting of hydrogen and an alkyl radical, to form a solution of said resin-coupler in said emulsion, and mixing said solution with a packet-forming compound selected from the class consisting of methylmethacrylate-methacrylic acid copolymer, algin, carboxymethyl cellulose, cellulose sulfate, and alkaline earth metal salts, to form a dispersion of particles of gelatin, silver halide and resincoupler combination, in a gelatin matrix or continuous phase of gelatin.
  • the method of claim 4, which comprises additionally forming in the same way as said dispersion, at least one other dispersion of particles of gelatin, silver halide and resin-coupler combination in gelatin matrix, said lastmentioned silver halide being sensitive to a region of the visible spectrum different from that to which said firstmentioned silver halide is sensitive, and said last-mentioned resin-coupler combination being different in structure from said first-mentioned resin-coupler combination, and mixing said dispersions of particles with a hydrophilic colloid solution.
  • the method of making a packet photographic emulsion which comprises mixing with a gelatino-silver halide emulsion a watersoluble salt of a resin-coupler compound of the recurring structure where R is selected from the class consisting of phenyl, carboxyalkyl and acyloxy radicals, x and y are selected from the class consisting of 0 and 1, and R represents a color-forming group including an aryl group, capable of reacting with the oxidation product of a primary aromatic amino developing agent, to form a solution of said resin coupler in said emulsion, and mixing said emulsion with a water-soluble salt of methylmethacrylate-methacrylic acid copolymer to form a dispersion of particles of gelatin, silver halide and resin-coupler combination, in a gelatin matrix or continuous phase of gelatin.
  • the method of claim 6, which comprises additionally forming in the same way as said dispersion, at least one other dispersion of particles of gelatin, silver halide and resin-coupler combination in gelatin matrix, said lastmentioned silver halide being sensitive to a region of the visible spectrum different from that to which said firstmentioned silver halide is sensitive, and said last-mentioned resin-coupler combination being different in structure from said first-mentioned resin-coupler combination, and mixing said dispersions of particles with a hydrophilic colloid solution.
  • a packet photographic emulsion which comprises mixing with a gelatino-silver halide emulsion a water-soluble salt of a resin-coupler compound of the recurring structure where R is selected from the class consisting of phenyl, carboxyalkyl and acyloxy radicals, x and y are selected from the class consisting of O and 1, and R represents a color-forming group including an aryl group, capable of reacting with the oxidation product of a primary aromatic amino developing agent, to form a solution of said resin coupler in said emulsion, and then adding said solution and a solution of a calcium salt, slowly and with stirring to another solution of said calcium salt to form a dispersion of particles of gelatin, silver halide ad calcium salt of said resin coupler, in a gelatin matrix or continuous phase of gelatin.
  • the method of claim 8, which comprises additionally forming in the same way as said dispersion, at least one other dispersion of particles of gelatin, silver halide and resin-coupler combination in gelatin matrix, said lastmentioned silver halide being sensitive to a region of the visible spectrum different from that to which said firstmentioned silver halide is sensitive, and said last-mentioned resin-coupler combination being different in structure from said first-mentioned resin-coupler combination, and mixing said dispersions of particles with a hydrophilic colloid solution.
  • the method of making a mixed packet photographic emulsion which comprises mixing with a redsensitive gelatino silver halide emulsion the sodium salt of a resin coupler compound of the recurring structure where R represents an o-hydroxy-substituted phenyl radical, to form a solution of said resin coupler in said emulsion, mixing said solution with a solution of a watersoluble salt of methylmethacrylate-mcthacrylic acid copolymer to form a dispersion of particles of gelatin, redsensitive silver halide and resin-coupler combination in a gelatin matrix or continuous phase of gelatin, and forming in the same way as said first-mentioned dispersion a second dispersion of particles of gelatin, blue-sensitive silver halide and resin-coupler compound of the composition cmoHoH-cH where R represents the residue of a benzoyl acetyl group, in a gelatin matrix or continuous phase of gelatin, and mixing said dispersions of particles.
  • a light-sensitive photographic emulsion comprising packets or discrete particles of gelatin, silver halide and salt of a non-diffusing resin-coupler compound of the recurring structure where R is selected from the class consisting of phenyl, carboxyalkyl and acyloxy radicals, x and y are selected from the class consisting of 0 and 1, R represents a colorforming group including an aryl group, capable of reacting with the oxidation product of a primary aromatic amino developing agent, and R is selected from the class consisting of hydrogen and an alkyl radical, said packets or discrete particles being dispersed in a matrix or continuous phase of hydrophilic water-permeable colloid.
  • a light-sensitive photographic emulsion comprising packets or discrete particles of gelatin, silver halide and salt of a non-diffusing resin-coupler compound of the recurring structure O CO- in M W where R represents the residue of a benzoyl acetyl group.

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  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
US345626A 1953-03-30 1953-03-30 Mixed packet photographic emulsions using resin couplers Expired - Lifetime US2698797A (en)

Priority Applications (5)

Application Number Priority Date Filing Date Title
BE527703D BE527703A (it) 1953-03-30
US345626A US2698797A (en) 1953-03-30 1953-03-30 Mixed packet photographic emulsions using resin couplers
GB8535/54A GB767028A (en) 1953-03-30 1954-03-24 Method of making photographic emulsions for colour photography
DEE8779A DE1009023B (de) 1953-03-30 1954-03-27 Verfahren zur Herstellung einer farbenphotographischen Mischemulsion
FR1105868D FR1105868A (fr) 1953-03-30 1954-03-30 Procédé de préparation de produits photosensibles et nouveaux produits obtenus

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BE (1) BE527703A (it)
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FR (1) FR1105868A (it)
GB (1) GB767028A (it)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4119463A (en) * 1975-04-24 1978-10-10 Mitsubishi Paper Mills, Ltd. Photographic binder comprising isobutylene-maleic anhydride copolymer
US5399480A (en) * 1993-09-14 1995-03-21 Eastman Kodak Company Attachment of gelatin-grafted polymer particles to pre-precipitated silver halide grains
US5441865A (en) * 1993-01-07 1995-08-15 Eastman Kodak Company Gelatin-grafted-polymer particles as peptizer for silver halide emulsions

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2422680A (en) * 1944-06-01 1947-06-24 Du Pont Process for preparing hydrophilic color-former silver halide dispersions
US2463794A (en) * 1944-08-30 1949-03-08 Du Pont Preparation of colloid color former silver halide dispersions

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
None *

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4119463A (en) * 1975-04-24 1978-10-10 Mitsubishi Paper Mills, Ltd. Photographic binder comprising isobutylene-maleic anhydride copolymer
US5441865A (en) * 1993-01-07 1995-08-15 Eastman Kodak Company Gelatin-grafted-polymer particles as peptizer for silver halide emulsions
US5503972A (en) * 1993-01-07 1996-04-02 Eastman Kodak Company Gelatin-grafted-polymer particles as peptizer for silver halide emulsions
US5399480A (en) * 1993-09-14 1995-03-21 Eastman Kodak Company Attachment of gelatin-grafted polymer particles to pre-precipitated silver halide grains
US5741633A (en) * 1993-09-14 1998-04-21 Eastman Kodak Company Attachment of gelatin-grafted polymer particles to pre-precipitated silver halide grains

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DE1009023B (de) 1957-05-23
BE527703A (it)
FR1105868A (fr) 1955-12-08

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