US3929485A - Dispersion of silver halide developing agent with surface active polymers of maleic acid half esters - Google Patents

Dispersion of silver halide developing agent with surface active polymers of maleic acid half esters Download PDF

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US3929485A
US3929485A US492312A US49231274A US3929485A US 3929485 A US3929485 A US 3929485A US 492312 A US492312 A US 492312A US 49231274 A US49231274 A US 49231274A US 3929485 A US3929485 A US 3929485A
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sodium
silver halide
developing agent
halide developing
polyoxyethylene
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US492312A
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Masami Miyakawa
Masakazu Yoneyama
Nobuo Yamamoto
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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
    • G03C8/00—Diffusion transfer processes or agents therefor; Photosensitive materials for such processes
    • G03C8/32—Development processes or agents therefor
    • G03C8/36—Developers
    • 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
    • G03C2200/00—Details
    • G03C2200/47—Polymer

Definitions

  • ABSTRACT A dispersion comprising an hydrophilic organic colloid, fine droplets of silver halide developing agent dissolved in a substantially water-insoluble solvent, and a surface active polymer containing therein recurring units represented by the formula (I):
  • R is a hydrocarbon chain or fluorine substituted hydrocarbon chain containing 4 to 22 carbon atoms, or an aryl group
  • n is 0 or an integer of 1 to 40
  • M is a hydrogen atom or a cation.
  • the present invention relates to a dispersion of a silver halide developing agentin a hydrophilic organic colloid, which is contained in a color photographic element.
  • the dispersion is applicable particularly to the diffusion transfer color process.
  • a photographic element comprising a silver halide emulsion layer and a layer containing a dye developer which is diffusible in an alkaline solution (a dye which acts to develop silver halide), is exposed to form a latent image in the silver halide and is processed with an alkaline composition which can permeate the silver halide emulsion layer and the layer containing the dye developer, whereby the latent image is developed with the dye developer which is diffused with the alkali and at the same time, an oxidation product of the dye developer is produced and is rendered essentially non-diffusible in the hydrophilic colloidal layer.
  • a dye developer which is diffusible in an alkaline solution
  • the unoxidized dye developer is partially or entirely transferred to an image receiving element overlaid thereon through diffusion, thereby providing a positive dye image.
  • a dye former which provides a cyan transfer image is present in a red sensitive emulsion layer or in a colloidal layer adjacent the emulsion layer.
  • a dye former which provides a magenta transfer image is present in a green sensitive emulsion layer or in a colloidal layer adjacent the emulsion layer.
  • a dye former which provides a yellow transfer image is present in a blue sensitive layer or in a colloidal layer adjacent the emulsion layer.
  • a photosensitive element comprising the above described red sensitive layer, green sensitive layer, and blue sensitive layer is exposed and treated with an alkaline composition, whereby a multicolor positive image is transferred to a receiving element overlaid on the photosensitive element.
  • auxiliary developing agents are used to facilitate the development of the silver halide and the fixing of the dyes in the photosensitive element.
  • the auxiliary developing agents are colorless, waterinsoluble, and soluble and diffusible in an alkaline solution through a hydrophilic organic layer such as gelatin.
  • the colloidal particles of the dye developer or the auxiliary developing agent be as small as possible and thus that the surface thereof be as large as possible. The reason is that the dissolution, diffusion and permeation of the dye developer or the auxiliary developing agent in the alkaline solution at the developing step is effected through the interface between the dispersed particles and the gelatin gel.
  • the surface chemical techniques surface active agents are generally used as an emulsifying agent.
  • the emulsifying agent is effective in not only preparing fine particles, but providing storage stability for the particles for a long period of time.
  • the dispersion is stored after cool-setting or removing the solvent of the developing agent by evaporation or washing for the purpose of preventing the recombination of colloidal particles and preventing the crystal growth of the developing agent. With this procedure, however, it is difficult to store the dispersion for a long period of time while maintaining a fine particle size and without causing a crystalization of the developing agent. It is particularly difficult to eliminate the crystalization in the developing agent dispersion layer after the layer is coated and dried.
  • the dye developer should be non-diffusible and should not form coarse crystal grains in the photosensitive element prior to the alkaline solution processing and during the alkaline solution processing and it should be diffusible in the hydrophilic colloid.
  • the introduction of various oleophilic substitutents in the dye developer will render the dye developer easily soluble in a water-insoluble solvent for dispersion, but diffusion of the resulting dye developer is difficult at the processing stage. Thus, it is generally impossible to introduce a highly oleophilic substituent. In general, therefore, the dye developer has a low degree of disperability in the water-insoluble solvent and coarse crystal grains tend to form in a dispersion thereof in an aqueous gelatin solution.
  • the emulsifying agent has excellent emulsifying and dispersing capability, but has low surface activity and low spreadability, the coating of the emulsion becomes difficult.
  • the techniques to sufficiently finely disperse 'th'edyedeveloper, to prevent the dye developer from becoming coarse-grained, and to provide the dye developer with high reactivity and diffusibility with the alka- 'line'solutii'yn for developing silver halide in the adjacent layer are quite specific and conventionally used emul- 'si fyingand dispersing techniques can not be applied to achiev' 'ethese results.
  • lt is an ob jec t of the present invention .to provide a dispersion wherein a compound capable of acting as a reductant for an exposed silver halide, such as a dye developer, and/or an auxiliary developing agent (which developing agen tf or developing agents are herein referred to-as a silver halidedeveloping agent), is contained in a hydrophilic organic colloid in the vform of fine colloidal particles without adversely affecting the photographic properties.
  • a compound capable of acting as a reductant for an exposed silver halide such as a dye developer, and/or an auxiliary developing agent (which developing agen tf or developing agents are herein referred to-as a silver halidedeveloping agent)
  • auxiliary developing agent which developing agen tf or developing agents are herein referred to-as a silver halidedeveloping agent
  • R is a hydrocarbon chain or fluorine substituted hydrocarbon chain containing 4 to 22 carbon atoms, or an aryl group; n is O or an integer of l to 40; and M is a hydrogenatom or a cation.
  • hydrocarbon chain orfluorinei substituted hydro carbon chain can be .a straight. or branched chain, or
  • hydrocarbon chains having 4 to 22 carbon atoms include n-butyl, sec-butyl-,- iso-butyl, tert-butyl, n-amyl, isoamyl, neopentyl, tert-amyl, n-hexyl, pinacolyl, n-heptyl, pentamethylethyl, n-octyl, iso-octyl, n-nonyl, ndecyl, n-dodecyl, n-tetradecyl, n-hexadecyl, n-pentadecyl, n-eicosyl, etc.
  • fluorine substituted hydrocarbon chains, having 4 to 22 carbon atoms include 3,3,4,4-tetrafluorobutyl, dodeca
  • aryl groups are unsubstituted aryl groups such as phenyl and 'naphthyl, and substituted aryl groups containing substituents such as alkyl, e.g., dodecyl; alkylamino, e.g., oleylamino; alkoxycarbonyl, e.g., octoxycarbonyl; acyloxy, e.g., octanoyloxy; acylamino, e.g., octanoylamino; alkylcarbamyl, eg, octylcarbamoyl; and the like.
  • These aryl groups suitably contain up to 22 carbon atoms, e.g., 6
  • M are hydrogen ion, and cations, e.g alkali metal ions such as sodium ion, potassium ion and the like, ammonium ion, and trialkyl ammonium ion such as trimethyl ammonium ion, etc.
  • the surface active polymers containing the recurring unit represented by the above described formula include those copolymers produced from maleic anhydride or maleic acid half ester salts, and monomers copolymerizable therewith, such as ethylene,- styrene, methyl vinyl ether, methyl methacrylate, ethyl acrylate, acrylonitrile, acrylamide, vinyl acetate, vinyl chloride, and the like.
  • Thepolymer produced from maleic anhydride must be cleaved by alcohol decomposition.
  • the present invention is not limited tothe above described polymers only and all the polymers containing the above recurring unit can be used in the present invention. Polymers are suitable to achieve the objects of thisinvention as long as the amount of the repeating unit of the formula (I) is at least 10 percent by weight.
  • Compound 8 (molar ratio of x to y: 1:1)
  • Compound 9 (molar ratio of x to y: 3:1)
  • Compound 10 (molar ratio of x to y: 2:1)
  • Compound 11 (molar ratio of x to y: 1:1)
  • Compound 12 v(molar ratio of x to y: 1:1)
  • the copolymers can be easily produced in a conventional manner, e.g.,.*as disclosed in US. Pat; Nos. 3,549,605; 3,448,708; and 3,525,620.
  • the molecrange from about 250 to 100,000.
  • the molecular weight of the copolymers ranges from about 1,000 to- 20,000.
  • the amount of the surface active polymer added varies depending on the kind of silver halide developing agent and the solvent, and the amount of the silver halide developing agent and solvent, and the amount can range up to about 200% by weight.
  • the surface active polymer can be used alone or in combination with surface active agents with anionic and nonionic surface active agents being preferred.
  • Suitable surface active agents include the following examples. Aliphatic acid salts:
  • Alkylsulfonates zsodium dodecylsulfonate, sodium hexadecanesulfonate, sodium octadecanesulfonate, etc., Alkylarylsulfonates:
  • potassium octylbenzenesulfonate sodiumnonylbenzenesulfonate, sodium decylbenzenesulfonate, sodium undecylsulfonate, sodium dodecylbenzenesulfonate, sodium tridecylbenzenesulfonate, sodium dibutylnaphthalenesulfonate, sodium decylnaphthalenesulfonate,
  • ular weight of the copolymers is not limited and can 8 Alkyldiphenylether sulfonates:
  • polyoxyethylene lauryl ether polyoxyethylene oleyl ether, sodium polyoxyethylene lauryl ether sulfate,
  • polyoxyethylene sorbitan monolauric acid ester polyoxyethylene sorbitan inonostearic acid ester, polyoxyethylene monooleic acid ester, polyoxyethylene sorbitan monopalmitic acid ester, polyoxyethylene trioleic acid ester, etc.
  • the dye developers as used in the present invention are dye developers, which'are described in US. Pat.
  • the dye developers are characterized in that they are slightly soluble in water and non-diffusible under acidic and neutral conditions and they are diffusible under alkaline condition.
  • Representative examples of the dye developers include the-following compounds.
  • silver halide developing agents are generally I 2 I dissolved in a high boiling solvent (e.g., above 150C) CH and, if desired, an auxiliary solvent, and dispersed in an 5 about 1 to by weight, preferably about 10% by 011 weight, aqueous solution of a hydrophilic organic colloid such as gelatin, in the form of fine colloidal partil4'bls[(Y'HydrOqumOHyI'a'methYI)' cles, having a particle size of less than about 1 [1,, prefpropylamino]- 5,8,9,lO-tetrahydroxyanthracene erably less than 0.5 [1,.
  • a hydrophilic organic colloid such as gelatin
  • aparticle size of about 0.3 fluoroacetoxy-B-phenylethyl)phenylazo]-5- 20 M can be used hydroxypyrazole lactone
  • dea-[p-(2,5-Butyroyloxy-B-phenylethyl)-phenylaz0l-B- sired they can be used in combination with each other.
  • the high boiling solvent is an organic solvent Suitable auxiliary developing agents are described in which is used for dispersing the silver halide developing British Pat.
  • xili ry substantially water-insoluble and preferably has a boildeveloping agents are phenylhydroquinone,2-hydroxyi poinlt hi h than b t 150C, Th hi h b iling phetilzyIhyldrocl liliircilonq phenoiiylltiycggotc lumone, hth4- solvent is normally a liquid or a low melting solid at me yp eny y roquinone, 1 y roxynap aroom temperature.
  • the following can be 2-(4-aminophenethyl)-5-methylhydroquinone, 4- aminophenethylhydroquinone, 2,5-dimethoxyhydroquinone, 2,S-dibutoxyhydroquinone, m-xylohydroquinone, brornohydroquinone, 3,6-dichlorohyused: phosphoric acid esters such as triethyl phosphate, tri-n-butyl phosphate, triphenyl phosphate, tricresyl phosphate, tri-p-tert-butylphenyl phosphate, tri-2- ethylhexyl phosphate, and the like; phthalic acid esters such as methyl phthalate, ethyl phthalate, n-butyl phthalate, 2-ethylbutyl phthalate, n-propyl phthalate,
  • the auxiliary solvent is effective in that when used in combination with the high boiling solvent, the solubility of the dye developer and the auxiliary developing agent is increased and the grain size of the dispersion is reduced.
  • the auxiliary solvent can be removed from the dispersion containing the high boiling solvent by airdrying or washing. 1
  • auxiliary solvents are esters such as fl-ethoxyethyl acetate, fi-butoxy-B-ethoxyethyl acetate, tetrahydrofurfuryl adipate, ethyleneglycol monoacetate, methoxy triglycol acetate, ethyleneglycol monomethyl ether acetate, methyl acetate, ethyl acetate, propyl acetate, butyl acetate, isopropyl acetate, ethyl propyonate, and the like; alcohols such as diacetone alcohol, ethylene ,glycol, diethylene glycol,
  • ketones such as methyl isobutyl ketone, methyl isopropyl ketone, acetonylacetone, cyclohexanone, 2-methylcyclohexanone, ;3-rnethylcyclohexanone, 4-methylcyclohexanone, and the like
  • ethers such as diethylene glycol monobutyl ether, ethylene glycol monobutyl ether, diethylene glycol monoethyl ether, ethylene glycol monomethyl ether and the like; carbon tetrachloride and chloroform; etc.
  • the ratio of the silver halide developing agent to the binder is preferably in the range of about 2:1 to 1:2.
  • the dispersion of the present invention can contain, if desired, other additives.
  • the stability of the dispersion can be increased.
  • Suitable examples thereof include polyvinyl acetate, polyvinyl butyral, polyvinyl chloride, polyvinyl propionate, polymethyl acrylate, polyethyl acrylate, polybutyl acrylate, polypropyl acrylate, polymethylmethacrylate, polyethylmethacrylate, polybutylmethacrylate, polypropylmethacrylate, etc.
  • a viscosity increasing agent the stability of the dispersion can be increased.
  • a hardening agent such as' formaldehyde, mucochloric acid, 2- hydroxyl-4,6-dichloro-s-triazine sodium salt, etc., can be added to harden the coated layer.
  • the silver halide developing agent of the present invention is rendered free from the separation of the silver halide developing agent and coarse-graining of the fine liquid particles of the water-insoluble solvent in which the silver halide developing agent is contained, for a long period of time, and thus it is quite stable.
  • the dispersion of the present invention can be employed in the photographic elements disclosed in U.S.
  • EXAMPLE 1 To a mixture of 15 ml of N,N-diethyl lauryl amide and 22 ml of cyclohexanone was added 10 g of yellow dye developer: 1-phenyl-3-N-n-hexylcarbamoyl-4-p- (2-hydroquinonylethyl)phenylazo-S-pyrazolone.
  • a 20% cyclohexanone solution of Compound 2 having an average molecular weight of about 4000 (in the amounts shown in Table 1) as the emulsifying agent and 2 ml of a 20% methanol solution of Span 20 (sorbitan monolauric acid ester produced by Atlas Powder Co.) were added and completely dissolved in the vicinity of about C.
  • the solution so prepared was added to g of a 10% aqueous solution of gelatin at about 80C and stirred moderately.
  • the resulting solution was dispersed with a colloid mill.
  • the dispersion so prepared was cool-set and stored.
  • the average grain size was about 0.3 to 0.4 u.
  • the emulsion was coated on a gelatin undercoated cellulose triacetate base in a thickness of about 3 p, and on the resulting layer a gelatin aqueous solution having the following composition was coated to provide a dry thickness of about 1 ,u,.
  • Example 1 Amount of Compound 2 Days until Crystals of the Yellow Dye Developer Separated EX M EXAMPLE6 The procedureiof Example 1 was repeated using 10 g of magenta dye developer: 2-p-(2 magenta dye developerz'. 2-p-(2-hydroquinonylethyl)- hydroquinonylethyl)-phenylazo-4-isopropoxy-l -naphphenylazo-4-isopropoxy-l-naphthol. I thol was added to 60 ml of 2-methylcyclohexanone. To
  • Example 1 was cp using ya cozted on the layer as prepared above m a thickness vof I ggig ii t '(hydroqumonylpropyl)ammq The resulting sample was stored under the conditions 1 Y fi i T 51 I l of 50C and 80% RH and the days until Crystal of the e ts o l f Y m a e dye developer separated, were measured.
  • Example 1 The procedure'of Example 1 was repeated using T bl 6 magenta' dye developer: l-acetoxy-2-p-( 2- y qu y y )-p y p p yph-' Amount of Aerosol or Days until Crystals of the Ma enta 1 Dye Developer Separate thale ne.
  • Example 2 The results are shown in Table 4. r s (days) I V I Z 1. o 4 Within 1 Table 4 0.8 Within 1 Amount of Compound 2 Days unt l Crystals of the'Magenta Dye Developer Separated 40 (grams) I V COMPARISON EXAMPLE 2 8:; i Moreth'afi V The procedure of Example 2 was repeated except 1.2 More than 10 that p-nonylphenoxypropylsulfonic acid sodium salt was used as the'emulsifying agent and dispersed in a l0% gelatin aqueous solution and that magenta dye developer; 2-p-(2-hydroquinonylethyl)-phenylazo-4- EXAMPLE 5 isopropoxy l-naphthol, was used. The procedure of Example 2 was repeated except The results obtained are shown in Table 7.
  • a silver halide developing agent dispersion which comprises a hydrophilic organic colloid having 'dispersed therein fine droplets of a silver halide developing agent dissolved in av substantially water-insoluble solvent, and at least one surface active polymer selected from the group consisting of the compounds represented by the following formulae (ll) and (Ill):
  • R is a hydrocarbon chain or a fluorine substituted hydrocarbon chain containing 4 to 22 carbon atoms or an aryl group, n is O or an integer of l to 40, and M is a hydrogen atom or a cation; and wherein the molar ratio of x to y ranges from 3:1 to 9:1.
  • the surface active agent is selected fromthe
  • the silver halide developing agent dispersion according to claim 1, wherein the hydrophilic organic colloid is selected from the group consisting of phthalated gelatin, polyvinyl alcohol, polyvinyl pyrrolidone, polyacrylamide, sodium polyacrylate, polyvinyl- 2-methyldiazole, acrylamide/l -vinyl-2- methylimidazole copolymers, acrylamide/imidazole copolymers, acrylamide/l -vinyl-2-methylimidazole/acrylic acid copolymers, nitrocarboxymethylcellulose, N-vinylpyrrolidone-acrylic acid copolymers, N-vinylpyrrolidone-acrylic acid-methylacrylate copolymers, vinylphthalimide-acrylic acid copolymers, cellulose acetate hydrogen phthalate, poly-N-methylmethacrylamide, dimethyl-aminoethylmethacrylateacrylic acid copolymers, dimethylamino-ethylme
  • the high boiling solvent is selected from the group consisting of phosphoric acid esters, phthalic acid esters, aliphatic dibasic acid esters, aliphatic monobasic acid esters, amides, imides, alcohols, ethers, ketones.
  • the high boiling solvent is selected from the group consisting of triethyl phosphate, tri-n-butyl phosphate, triphenyl phosphate, tricresyl phosphate, tri-p-tertbutylphenyl phosphate, tri- 2-ethylhexyl phosphate, methyl phthalate, ethyl phthalate, n-butyl phthalate, 2 ethylbutyl phthalate, n-propyl phthalate, n-amyl phthalate, isoamyl phthalate, n-octyl phthalate, fl-methoxyethyl phthalate, ditetrahydrofurfuryl phthalate, ditetrahydrofurfuryladipate, noctyladipate, Z-ethylhexyladipate, n-hexyladipate, 2- ethyl
  • the oleophilic polymer is selected from the group consisting of polyvinyl acetate, polyvinyl butyral, polyvinyl chloride, polyvinyl propionate, polymethyl acrylate, polyethyl acrylate, polybutyl acrylate, polypropyl acrylate, polymethylmethacrylate, polyethylmethacrylat'e, polybutylmethacrylate and polypropylmethacrylate.
  • 35 The silver halide developing agent dispersion according to claim 2, wherein a solution of the silver halide developing agent in a high boiling solvent is dispersed in an about 1 to 20% by weight aqueous solution of the hydrophilic organic colloid.

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  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Silver Salt Photography Or Processing Solution Therefor (AREA)
  • Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
US492312A 1973-07-26 1974-07-26 Dispersion of silver halide developing agent with surface active polymers of maleic acid half esters Expired - Lifetime US3929485A (en)

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4123330A (en) * 1975-10-16 1978-10-31 Konishiroku Photo Industry Co., Ltd. Color diffusion transfer process using benzyl alcohol and derivatives thereof
US4181527A (en) * 1977-03-31 1980-01-01 Fuji Photo Film Co., Ltd. Photographic material comprising organic solvent gelling agent
US4242444A (en) * 1977-07-04 1980-12-30 Konishiroku Photo Industry Co., Ltd. Process for the preparation of light-sensitive silver halide photographic material
US5422233A (en) * 1994-05-17 1995-06-06 Polaroid Corporation Photographic processing compositions including hydrophobically modified thickening agent

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0239363B1 (en) 1986-03-25 1992-10-28 Konica Corporation Light-sensitive silver halide photographic material feasible for high speed processing

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US2322027A (en) * 1940-02-24 1943-06-15 Eastman Kodak Co Color photography
US3121011A (en) * 1959-05-25 1964-02-11 Polaroid Corp Photographic products and processes
US3518088A (en) * 1965-12-17 1970-06-30 Eastman Kodak Co Developing agent dispersions
US3589902A (en) * 1965-12-22 1971-06-29 Agfa Gevaert Ag Photographic developer concentrate
US3647437A (en) * 1970-12-18 1972-03-07 Polaroid Corp Photographic products, processes and compositions
US3765897A (en) * 1970-10-09 1973-10-16 Agfa Gevaert Ag Process of incorporating additives into photographic emulsions
US3785824A (en) * 1971-09-24 1974-01-15 Minnesota Mining & Mfg Photographic aqueous dispersion concentrates

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BE543746A (en)) * 1955-08-11
US3359108A (en) * 1964-04-02 1967-12-19 Eastman Kodak Co Photographic emulsion having a low modulus of elasticity and process for its manufacture
DE1812578A1 (de) * 1968-10-04 1970-06-25 Wolfen Filmfab Veb Verfahren zur Herstellung von halogensilberhaltigen farbenfotografischen Materialien
DE1957467A1 (de) * 1969-11-15 1971-05-27 Heinz Reber Spanner fuer Betonschalungen
JPS5017637A (en)) * 1973-06-14 1975-02-25

Patent Citations (7)

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Publication number Priority date Publication date Assignee Title
US2322027A (en) * 1940-02-24 1943-06-15 Eastman Kodak Co Color photography
US3121011A (en) * 1959-05-25 1964-02-11 Polaroid Corp Photographic products and processes
US3518088A (en) * 1965-12-17 1970-06-30 Eastman Kodak Co Developing agent dispersions
US3589902A (en) * 1965-12-22 1971-06-29 Agfa Gevaert Ag Photographic developer concentrate
US3765897A (en) * 1970-10-09 1973-10-16 Agfa Gevaert Ag Process of incorporating additives into photographic emulsions
US3647437A (en) * 1970-12-18 1972-03-07 Polaroid Corp Photographic products, processes and compositions
US3785824A (en) * 1971-09-24 1974-01-15 Minnesota Mining & Mfg Photographic aqueous dispersion concentrates

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4123330A (en) * 1975-10-16 1978-10-31 Konishiroku Photo Industry Co., Ltd. Color diffusion transfer process using benzyl alcohol and derivatives thereof
US4181527A (en) * 1977-03-31 1980-01-01 Fuji Photo Film Co., Ltd. Photographic material comprising organic solvent gelling agent
US4242444A (en) * 1977-07-04 1980-12-30 Konishiroku Photo Industry Co., Ltd. Process for the preparation of light-sensitive silver halide photographic material
US5422233A (en) * 1994-05-17 1995-06-06 Polaroid Corporation Photographic processing compositions including hydrophobically modified thickening agent

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JPS5034233A (en)) 1975-04-02
DE2436185A1 (de) 1975-02-06

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