US3912517A - Method of incorporating photographic ingredients into hydrophilic colloids - Google Patents

Method of incorporating photographic ingredients into hydrophilic colloids Download PDF

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US3912517A
US3912517A US450322A US45032274A US3912517A US 3912517 A US3912517 A US 3912517A US 450322 A US450322 A US 450322A US 45032274 A US45032274 A US 45032274A US 3912517 A US3912517 A US 3912517A
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water
surface active
ingredient
hydrophilic colloid
photographic
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Poucke Raphael Karel Van
Vugt Jaak Pieter Van
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Agfa Gevaert NV
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Agfa Gevaert NV
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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
    • G03C7/3885—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 solvent

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  • Daniel ABSTRACT A method is described of incorporating a substantially water-insoluble photographic ingredient into a photographic hydrophilic colloid layer by the steps of dissolving said ingredient in an organic solvent having a solubility in water of at most 25 by weight at 20C, admixing the organic solution thus obtained with water in the presence of a surface active agent but in the absence of a hydrophilic colloid, removing the said organic solvent forming thereby a dispersion of the said ingredient in water and incorporating the dispersion thus formed in the said hydrophilic colloid coating composition, characterized in that the said organic solution of photographic ingredient is admixed with water in the presence of an anionic surface active agent comprising in its molecule a hydrophobic hydrocarbon group of at least 8 C-atoms and a hydrophilic SO M or -OSO M group wherein M is hydrogen, an alkali metal atom, ammonium or organic ammonium and a non-ionic surface active hydroxy compound so that the l-lLB-index of the combination of surface active compounds is comprise
  • the present invention is concerned with a method of incorporating photographic ingredients into hydrophilic colloid compositions, more especially with a method of making stable dispersions in water of such ingredients from which they can be homogeneously distributed into hydrophilic colloid coating compositions for forming one of the water-permeable layers of a photographic silver halide element.
  • the method of the present invention is an improvement of the method of the British Pat. Specification 1,297,947 filed Mar. 20, 1969 by Gevaert-Agfa N.V. corresponding to US. pat. No. 3,658,546.
  • a photographic ingredient having a solubility in water at C of not more than 3 7r by weight is incorporated into a hydrophilic colloid coating composition for forming a waterpermeable colloid layer of a light-sensitive silver halide element, by a method which comprises dissolving said ingredient in a mainly water-immiscible organic solvent, admixing the solution thus obtained with water in the presence of a surface active agent but in the absence of a hydrophilic colloid, removing the said organic solvent forming thereby a dispersion of the said ingredient in water and incorporating the dispersion thus formed in the said hydrophilic colloid coating composition, wherein the said mainly water-immiscible solvent has a solubility in water of not more than by weight at 20C.
  • the dispersion of ingredient in water formed need not be added directly to the hydrophilic colloid coating composition of the layer into which the said component should be present e.g. a light-sensitive silver halide emulsion layer. It is possible to create stocks of the dispersion of the photographic ingredients in water and to take part of the preformed dispersion for addition to the hydrophilic colloid coating composition whenever needed.
  • the method of the British Patent Specification has several advantages over the dispersion techniques according to which the organic solution of the photographic ingredient is dispersed into an aqueous hydrophilic colloid medium, in particular aqueous gelatin, from which the solvent is removed and which can be admixed afterwards with a lightsensitive silver halide emulsion.
  • removal-of the solvent from the dispersion in water is much easier to effect than removal from the gelatin composition.
  • the dispersion of the photographic ingredients in water remains liquid and can be stored at room temperature whereas the gelatin compositions, even gelatin compositions comprising as low as 1 7c of gelatin, should be stored at temperatures below room temperature whereby they become solid and should be remelted at the stage of addition to the hydrophilic colloid coating composition.
  • the dispersions of photographic ingredients in water can comprise markedly higher concentrations of ingredient than the preformed gelatin dispersions.
  • preformed dispersions in gelatin when preformed dispersions in gelatin are made an extra amount of gelatin is added to the hydrophilic colloid coating composition which increases the coating thickness or in the case of colour couplers conversely decreases the dye density which can be obtained for a given coating thickness.
  • phenolic compounds should be added to the preformed gelatin dispersions in order to protect the gelatin against degeneration.
  • the stability of the dispersions of the photographic ingredients is not always sufficient either during storing of the aqueous dispersions or after addition to the hydrophilic colloid coating composition.
  • the dimensions of the dispersed particles are sometimes not sufficiently small which may give rise to undesirable turbidity of the coated layers.
  • the dispersing agent causes undesirable foaming or poses difficulties on coating the hydrophilic colloid coating composition e.g. as regards uniformity of coating thickness.
  • an anionic surface active agent especially a surface active agent comprising in its molecular structure a hydrophobic hydrocarbon group of at least 8 C- atoms, preferably from about 8 to about 24 C-atoms and a hydrophilic SO M or OSO M group wherein M is hydrogen, an alkali metal atom, ammonium or organic ammonium, together with a non-ionic surface active agent, especially a non-ionic surface active hydroxy compound.
  • Non-ionic surface active agents cannot be used alone in the method of the British specification because it is not possible to form dispersions in water of sufficiently small particle size and because they give rise to repellency spotsin the coated layers.
  • the present invention provides a method of incorporating a photographic ingredient having a solubility in water at 20C of not more than 3 72 by weight into a hydrophilic colloid coating composition for forming a water-permeable colloid layer of a light-sensitive silver halide element, which comprises in accordance with the British Patent Specification the steps of dissolving said ingredient in an organic solvent having a solubility in water of at most 25 by weight at 20C, admixing the organic solution thus obtained with water in the presence of a surface active agent, removing the said organic solvent forming thereby a dispersion of the said ingredient in water, and incorporating the dispersion thus formed in the said hydrophilic colloid coating composition with the modification that the said organic solution of photographic ingredient is admixed with water in the presence of an anionic surface active agent comprising in its molecule a hydrophobic hydrocarbon group of at least 8 C-atoms and a hydrophilic -SO M or OSO;;M group wherein M is hydrogen, an alkali metal atom,
  • the method of the present invention is useful for incorporating photographic ingredients having a solubility in water at 20C of at most 3 by weight and thus is particularly concerned with photographic ingredients that comprise a ballasting hydrophobic group of at least 8 C-atoms and that do not contain strongly watersolubilizing groups such as carboxy and sulpho groups.
  • These ingredients are for example photographic couplers as used in colour photography which upon colour development couple with the oxidation products of aromatic primary amino colour developing agents, maskforming compounds as used in colour photography which oxidatively couple with a colour coupler in an oxidizing bleaching bath as described for example in UK. Pat. No. 880.862 filed Dec. 31, 1956 and 975,932 filed Nov.
  • dyes which include spectrally sensitizing dyes and light-screening dyes e.g. antihalation and filter dyes, emulsion stabilizing agents and anti-oxidation agents, developing agents including tanning developing agents and developing agent precursor compounds and other photographically active ingredients.
  • the anionic surface active agents of use according to the present invention comprise a hydrophobic hydrocarbon group of at least 8 C- atoms, preferably from about 8 to about 24 C-atoms, and a hydrophilic -SO;,M or OSO M group wherein M is hydrogen, an alkali metal atom, ammonium or organic ammonium.
  • anionic surface active agents are well known in the art and include the following non-limitative groups of compounds 1.
  • X stands for alkylene, aralkylene or arylene
  • Y stands for oxygen or sulphur
  • A is alkylene, substituted alkylene e.g. alkylene substituted by hydroxyl, or aralkylene.
  • R represents a branched-chain or straight-chain aliphatic group as defined for R derived from a carboxylic acid e.g. capric, lauric, myristic, palmitic, stearic, behenic and oleic acid.
  • sodium hydroabietyl sulphate 17.
  • sodium isohexadecyl sulphonate 18.
  • ethoxylated alcohols include ethoxylated alcohols and phenols e.g. the reaction product of an alcohol or phenol with more than one mole, preferably 3 to 50 moles of ethylene oxide.
  • Suitable alcohols which may be ethoxylated are C -C aliphatic alcohols, oleyl alcohols, oxo alcohols, the so-called Ziegler alcohols, ether alcohols, secondary alcohols, alkyl phenols, alkylated-B-naphthol, complex phenols derived from condensatin of a simple phenol with an aldehyde or ketone e.g. phenol with an alkyl cyclohexanone, etc.
  • non-ionic surface active compounds are esters from branched-chain or straight-chain fatty acids comprising at least 12 C-atoms e.g. lauric acid, myristic acid, palmitic acid, stearic acid and oleic acid, and polyhydroxy compounds e.g. ethylene glycol, propylene glycol, glycerol, diethylene glycol, polyethylene glycol, pentaerythritol, hexitol anhydrides e.g. sorbitan, isosorbitol, mannitan and isomannitol, polyoxyethylene derivatives of hexitolanhydrides, etc.
  • lauric acid e.g. lauric acid, myristic acid, palmitic acid, stearic acid and oleic acid
  • polyhydroxy compounds e.g. ethylene glycol, propylene glycol, glycerol, diethylene glycol, polyethylene glycol, pentaerythritol, hexito
  • Preferred non-ionic surface active agents for use according to the present invention are ethoxylated alkyl phenols having from 3 to 50 recurring ethylene oxide units e.g. ethoxylated phenols carrying one or more C -C linear or branched alkyl substituents such as isooctyl phenol, nonylphenol and isononylphenol and esters of hexitol anhydrides or polyethylene oxide derivatives thereof obtained by esterification of 1 or 2 hydroxy] groups of the hexitolanhydride with branched-chain or straight-chain C, C fatty acids, e.g. sorbitan monostearate, sorbitan monolaurate and polyoxyethylene sorbitan monostearate.
  • C fatty acids e.g. sorbitan monostearate, sorbitan monolaurate and polyoxyethylene sorbitan monostearate.
  • the dispersion into water of the organic solution of the ingredient may be assisted by the use of high speed stirrers, homogenizers (single or double stage homogenizers), colloid mills and ultrasonic wave generators.
  • the anionic as well as the non-ionic surface active agents employed in making the dispersions in water according to the present invention may be present in the water into which the organic solution of the photographic ingredient is dispersed.
  • the non-ionic surface active agent is used at the stage of dissolving the photographic ingredient in the sparingly water-soluble organic solvent whereas the anionic surface active agent is used at the stage of dispersing the organic solution in the water.
  • the amount of dispersing agents or wetting agents used in making the dispersions in water of photographic ingredients according to the method of the present invention may vary within very wide limits; it is generally comprised between 1 and 20 by weight relative to the weight of ingredient to be dispersed.
  • the ratio of anionic to non-ionic surface active agent is such that a HLB-index comprised between about 8 and about 18'is obtained.
  • the organic solvents from which the photographic ingredients are dispersed in water have a solubility in water of at most 25 by weight at room-temperature (20C). Solvents having a solubility in water comprised between 2 and by weight at room-temperature are preferred. Moreover, said solvents preferably are lowboiling solvents i.e. solvents having a boiling point of at most 130C and a sufficiently high vapour pressure so that they can still be removed readily from the aqueous dispersion by applying a vacuum of 500 to 10 mm Hg at a temperature of 25 to 80C.
  • Suitable mainly water-immiscible solvents for use according to the present invention are methylene chloride, ethyl formate, n-butyl formate, ethyl acetate, n-propyl acetate, isopropyl acetate, butyl acetate, methyl propionate, ethyl propionate, diethyl carbonate, carbon tetrachloride, sym.tetrachloroethane, 1,1,2-trichloroethane, 1,2-dichloropropane, chloroform, n-butyl alcohol, diethyl ketone, methyl npropyl ketone, diisopropyl ether, cyclohexane, methyl cyclohexane, benzene, toluene and nitromethane.
  • oil-former which is a water-immiscible organic crystalloidal solvent having a boiling point above 175C e.g. tricresyl phosphate, tributyl phthalate,'dibu tyl phthalate, diisooctyl phthalate, tributyl citrate, dibutyl sebacate, N,N'-dimethyl palmitamide, etc. and which is left in the dispersion after removal of the waterimmiscible low-boiling organic solvent referred to hereinbefore.
  • oil-formers are well known in the art for use in dispersing photographic ingredients e.g. colour couplers in photographic hydrophilic colloid coating compositions.
  • the water-miscible solvents are readily removed from the aqueous dispersion together with the waterimmiscible solvents, unless they have too low a vapourpressure to be removed with the water-immiscible solvents, in which case they are left in the dispersion of component in waterfrom which they are incorporated into the hydrophilic colloid composition for forming a layer of a photographic material.
  • the water-miscible solvents left in this hydrophilic colloid composition can be removed therefrom unless this is deemed unnecessary because they will have no disadvantageous effect on the physical or photographic properties by washing the chilled and thereby gelled colloid composition.
  • water-miscible solvents that are suitable for use in conjunction with the substantially waterimmiscible solvents are methanol, ethanol, isopropyl alcohol, dimethyl sulphoxide, tetrahydrofuran, N-methyl-2-pyrrolidone, dioxan, dimethyl formamide, dimethoxyethane, formamide, ethylene glycol, acetonitrile, acetone, butyrolactone, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, diacetone alcohol and tetrahydrothiophene-l,1-dioxide.
  • the removal of the sparingly'water-miscible solvent from the aqueous dispersion may be achieved for instance by evaporation, if necessary, e.g. for accelerating the removal, by applying reduced pressure and/or moderate heating.
  • the said dispersion After removal of the sparingly water-miscible solvent from the aqueous dispersion, the said dispersion can be incorporated directly into the colloid coating composition of the layer into which the photographic ingredient is intended to be present. However, it is also possible to create stocks of the concentrated dispersions of the ingredient in water and to use parts of these stocks whenever required.
  • the hydrophilic colloid coating composition into which the aqueous dispersion of photographic ingredient is incorporated usually comprises gelatin as hydrophilic colloid although other hydrophilic colloidal materials or mixtures of them can be used too e.g. colloidal albumin, zein, casein, a cellulose derivative such as carboxymethyl cellulose, a synthetic hydrophilic colloid such as polyvinyl alcohol, poly-N-vinyl pyrrolidone, etc.
  • the said colloid coating compositions for forming a layer of a photographic material may of course contain in additioni to the colloid carrier all sorts of other ingredients e.g. light-sensitive silver halide and other silver halide emulsion ingredients.
  • the amount of stored dispersion to be added to the colloid coating composition of the photographic layer is such that the ingredient is present in the resulting layer in the desired concentration. This amount is naturally dependent on the concentration of said ingredient in said dispersion. In accordance with the present invention it was found possible in some instances to make stable dispersions of ingredients in water comprising up to 30 of said ingredient.
  • the HLB-value of the combination of surface active agents used was 14.
  • the ethyl acetate was removed in a thin-film evaporator under reduce pressure of 400 mm Hg at 55C leaving a stable dispersion of the colour coupler in water.
  • the dispersion of colour coupler in water was admixed by gentle stirring with a conventional gelatino red-sensitized silver halide emulsion ready for coating so as to disperse the colour coupler homogeneously throughout the emulsion.
  • Example 2 Example 1 was repeated with the only difference that now 0.9 g of SPAN 20 (trade name) and 3.5 ml of the 10 aqueous solution of TERGITOL 4 (trade name) was used.
  • the HLB-value of the combination of surface active agents used was 17.
  • EXAMPLE 3 10 g of the colour coupler of example 1 were dissolved in 30 ml of ethyl acetate comprising 1 g of HOS- TAPAL W (trade name of Farbwerke Hoechst, Frankfurt, W.GErmany for a polyoxyethylene ether of nonylphenol.)
  • the solution was dispersed by means of a high pressure homogenizer in 100 ml of water heated .to 55C and comprising 2 ml of a 10 7( aqueous solution of the sodium salt of oleyl methyl taurine.
  • the HLB-value of the combination of surface active agents was 8.
  • the dispersion was admixed by gentle stirring with a conventional gelatino red-sensitized silver halide emulsion ready for coating so as to disperse the colour coupler homogeneously throughout the emulsion.
  • EXAMPLE 4 10 g of the colour coupler of example 1 were dissolved in 30 ml of ethyl acetate comprising 0.9 g of SPAN 20 (trade name) and 10 g of tricresyl phosphate. The solution was dispersed by means of a high pressure homogenizer in 100 ml -of water heated to 55C and comprising 10 ml of a 5 aqueous solution of sodium isohexadecyl sulphate.
  • the HLB value of the combination of surface active agents was 18.
  • the stable dispersion was homogeneously mixed with a red sensitized gelatino silver halide emulsion ready for coating.
  • EXAMPLE 5 10 g of the cyan-forming colour coupler with formula
  • EXAMPLE 6 10 g of the yellow-forming colour coupler with formula 2)is a S m --NHCOCH,CO
  • the solution was dispersed in ml of water comprising 8 ml of a 5 aqueous solution of sodium isohexadecyl sulphate.
  • the HLB value of the combination of surface active agents was 18.
  • the stable dispersion obtained was mixed homogeneously with a blue-sensitive gelatino silver halide emulsion ready for coating.
  • EXAMPLE 7 10 g of the cyan-forming colour coupler with formula Chemical Industries Inc., Wilmington, Del., USA for a polyethylene sorbitan monostearate) were dissolved in 30 ml of ethyl acetate.
  • the solution was dispersed at 55C in 100 ml of water comprising 4ml of a 20 aqueous solution of MER- SOLAT H (trade name of Wegriken Bayer A.G., Leverkusen, W.Germany for an alkane sulphonate made by sulphochlorination and subsequent saponification of a mixture of saturated branched-chain as well as straight-chain hydrocarbons averaging 14 C-atoms obtained by hydrogenation of the so-called Kogasins, which are the hydrocarbon mixtures distilling in the range of 230-320C formed according to the Fisher- Tropsch hydrocarbon synthesis).
  • the HLB value of the combination of surface active agents was 13.
  • the stable aqueous dispersion was mixed by gentle stirring with a conventional red-sensitized silver halide emulsion.
  • the solution was dispersed by means of an Ultrasonic Emulsator based on the Pohlman whistle principle in 100 ml of water comprising 3.75 ml of a 10 aqueous solution of sodium .isotetradecyl sulphate.
  • the HLB value of the combination of surface active agents was 18. l
  • aqueous dispersions of colour couplers prepared as described in the above examples showed high stability and could be stored for weeks.
  • the stability of the dispersions was markedly better than that of dispersions prepared according to the method of the British patent specification wherein an anionic surface active compound was used alone.
  • a method of incorporating a photographic ingredient having a solubility in water at 20C of not more than 3 by weight into a hydrophilic colloid coating composition for forming a water-permeable colloid layer of a light-sensitive silver halide element which comprises the steps of dissolving said ingredient in an organic solvent having a solubility in water of at most 25 by weight at 20C, admixing the organic solution thus obtained with water in the presence of a surface active agent but in the absence of a hydrophilic colloid, removing said organic solvent forming thereby a dispersion of said ingredient in water and incorporating the dispersion thus formed in said hydrophilic colloid coating composition, the improvement which comprises admixing.
  • said organic solution of photographic ingredient with water in the presence of an anionic surface active agent comprising in its molecule a hydrophobic hydrocarbon group of at least 8 C-atoms and a hydrophilic -SO M or OSO ,M group wherein M is hydrogen, an alkali metal atom, ammonium or organic ammonium and a non-ionic surface active hydroxy compound in said proportions that the combined HBL- index of said surface active compounds is comprised between about 8 and about l8.
  • organic solution comprises in addition to said organic solvent a water-immiscible organic crystalloidal solvent having a boiling point above C.
  • non-ionic surface active agent is anethoxylated phenol carrying one or more linear or branched-chain C -C alkyl groups and comprising from 3 to 50 recurring ethylene oxide units.
  • nonionic surface active agent is an ester of a hexitolanhydride or polyoxyethylene ether thereof obtained by esterification of l or 2 hydroxyl groups of the hexitol anhydride with branched-chain or straight-chain C, C fatty acids 9.
  • hydrophilic colloid is gelatin.
  • hydrophilic colloid coating composition is a gelatino silver halide emulsion.

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  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Colloid Chemistry (AREA)
  • Silver Salt Photography Or Processing Solution Therefor (AREA)
  • Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
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Cited By (25)

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US4006025A (en) * 1975-06-06 1977-02-01 Polaroid Corporation Process for dispersing sensitizing dyes
US4073983A (en) * 1975-04-25 1978-02-14 United Chemical Corporation Method and composition for decreasing water resistance to movement
US4080209A (en) * 1975-07-03 1978-03-21 Fuji Photo Film Co., Ltd. Photographic light-sensitive material
US4105453A (en) * 1976-03-29 1978-08-08 Konishiroku Photo Industry Co., Ltd. Colored light-sensitive silver halide photographic material with coating additive
US4192683A (en) * 1975-12-17 1980-03-11 Konishiroku Photo Industry Co., Ltd. Photographic light-sensitive material
US4385110A (en) * 1975-05-02 1983-05-24 Fuji Photo Film Co., Ltd. Process for preparing color photographic light-sensitive materials
US4464464A (en) * 1981-07-30 1984-08-07 Agfa-Gevaert Aktiengesellschaft Color photographic recording material
US4624903A (en) * 1984-11-23 1986-11-25 Eastman Kodak Company Dispersions of water-insoluble photographic addenda with petroleum sulfonate
US4766061A (en) * 1985-11-21 1988-08-23 Eastman Kodak Company Photographic coupler dispersions
US4957857A (en) * 1988-12-23 1990-09-18 Eastman Kodak Company Stabilization of precipitated dispersions of hydrophobic couplers
US4970139A (en) * 1989-10-02 1990-11-13 Eastman Kodak Company Methods of preparation of precipitated coupler dispersions with increased photographic activity
US4988610A (en) * 1988-07-26 1991-01-29 Eastman Kodak Company Hydrophilic colloid compositions for photographic materials
US5015564A (en) * 1988-12-23 1991-05-14 Eastman Kodak Company Stabilizatin of precipitated dispersions of hydrophobic couplers, surfactants and polymers
US5051350A (en) * 1988-07-12 1991-09-24 Fuji Photo Film Co., Ltd. Process for preparing a silver halide emulsion
US5087554A (en) * 1990-06-27 1992-02-11 Eastman Kodak Company Stabilization of precipitated dispersions of hydrophobic couplers
US5089380A (en) * 1989-10-02 1992-02-18 Eastman Kodak Company Methods of preparation of precipitated coupler dispersions with increased photographic activity
US5104776A (en) * 1989-11-29 1992-04-14 Eastman Kodak Company Increased photographic activity precipitated coupler dispersions prepared by coprecipitation with liquid carboxylic acids
US5158863A (en) * 1989-01-17 1992-10-27 Eastman Kodak Company Methods of forming stable dispersions of photographic materials
US5182189A (en) * 1989-11-29 1993-01-26 Eastman Kodak Company Increased photographic activity precipitated coupler dispersions prepared by coprecipitation with liquid carboxylic acids
US5256527A (en) * 1990-06-27 1993-10-26 Eastman Kodak Company Stabilization of precipitated dispersions of hydrophobic couplers
US5356768A (en) * 1990-10-29 1994-10-18 Minnesota Mining And Manufacturing Company Light-sensitive silver halide color photographic elements containing surfactants with a combined HLB greater than 20
US5468598A (en) * 1994-04-18 1995-11-21 Eastman Kodak Company Solid particle dispersions for imaging systems
US5549845A (en) * 1990-07-26 1996-08-27 Eastman Kodak Company Dispersions and emulsions comprising a fatty acid ester to reduce viscosity
US5610002A (en) * 1992-11-12 1997-03-11 Eastman Kodak Company Photographic composition containing a thickening agent
US5657931A (en) * 1994-04-18 1997-08-19 Eastman Kodak Company Stable aqueous solid particle dispersions

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JPS5348734A (en) * 1976-10-15 1978-05-02 Mitsubishi Paper Mills Ltd Multiilayer color silver halide photographic material
IT1224317B (it) * 1988-05-10 1990-10-04 Minnesota Mining & Mfg Elemento fotografico sensibile alla luce non basato sull'argento e procedimento per incorporare composizioni idrofobein composizioni colloidali idrofile
US5013640A (en) * 1989-06-15 1991-05-07 Eastman Kodak Company Preparation of low viscosity small-particle photographic dispersions in gelatin

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US3658546A (en) * 1969-03-20 1972-04-25 Agfa Gevaert Nv Method of incorporating photographic ingredients into photographic colloid compositions
US3676141A (en) * 1968-08-22 1972-07-11 Fuji Photo Film Co Ltd Process for the preparation of color-photographic sensitive materials using nonionic and anionic surface active agents

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US2870012A (en) * 1955-12-23 1959-01-20 Eastman Kodak Co Microdispersions of photographic color couplers
GB1346426A (en) * 1970-08-13 1974-02-13 Agfa Gevaert Incorporating photographic compounds into hydrophilic colloids

Patent Citations (2)

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Publication number Priority date Publication date Assignee Title
US3676141A (en) * 1968-08-22 1972-07-11 Fuji Photo Film Co Ltd Process for the preparation of color-photographic sensitive materials using nonionic and anionic surface active agents
US3658546A (en) * 1969-03-20 1972-04-25 Agfa Gevaert Nv Method of incorporating photographic ingredients into photographic colloid compositions

Cited By (26)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4073983A (en) * 1975-04-25 1978-02-14 United Chemical Corporation Method and composition for decreasing water resistance to movement
US4385110A (en) * 1975-05-02 1983-05-24 Fuji Photo Film Co., Ltd. Process for preparing color photographic light-sensitive materials
US4006025A (en) * 1975-06-06 1977-02-01 Polaroid Corporation Process for dispersing sensitizing dyes
US4080209A (en) * 1975-07-03 1978-03-21 Fuji Photo Film Co., Ltd. Photographic light-sensitive material
US4192683A (en) * 1975-12-17 1980-03-11 Konishiroku Photo Industry Co., Ltd. Photographic light-sensitive material
US4105453A (en) * 1976-03-29 1978-08-08 Konishiroku Photo Industry Co., Ltd. Colored light-sensitive silver halide photographic material with coating additive
US4464464A (en) * 1981-07-30 1984-08-07 Agfa-Gevaert Aktiengesellschaft Color photographic recording material
US4624903A (en) * 1984-11-23 1986-11-25 Eastman Kodak Company Dispersions of water-insoluble photographic addenda with petroleum sulfonate
US4716099A (en) * 1984-11-23 1987-12-29 Eastman Kodak Company Dispersions of water-insoluble photographic addenda using petroleum sulfonate
US4766061A (en) * 1985-11-21 1988-08-23 Eastman Kodak Company Photographic coupler dispersions
US5051350A (en) * 1988-07-12 1991-09-24 Fuji Photo Film Co., Ltd. Process for preparing a silver halide emulsion
US4988610A (en) * 1988-07-26 1991-01-29 Eastman Kodak Company Hydrophilic colloid compositions for photographic materials
US5015564A (en) * 1988-12-23 1991-05-14 Eastman Kodak Company Stabilizatin of precipitated dispersions of hydrophobic couplers, surfactants and polymers
US4957857A (en) * 1988-12-23 1990-09-18 Eastman Kodak Company Stabilization of precipitated dispersions of hydrophobic couplers
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US4970139A (en) * 1989-10-02 1990-11-13 Eastman Kodak Company Methods of preparation of precipitated coupler dispersions with increased photographic activity
US5089380A (en) * 1989-10-02 1992-02-18 Eastman Kodak Company Methods of preparation of precipitated coupler dispersions with increased photographic activity
US5182189A (en) * 1989-11-29 1993-01-26 Eastman Kodak Company Increased photographic activity precipitated coupler dispersions prepared by coprecipitation with liquid carboxylic acids
US5104776A (en) * 1989-11-29 1992-04-14 Eastman Kodak Company Increased photographic activity precipitated coupler dispersions prepared by coprecipitation with liquid carboxylic acids
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Also Published As

Publication number Publication date
FR2237220A2 (enrdf_load_stackoverflow) 1975-02-07
BE812173R (nl) 1974-09-12
GB1460894A (en) 1977-01-06
DE2412428A1 (de) 1974-10-03
CH578193A5 (enrdf_load_stackoverflow) 1976-07-30
CA1020387A (en) 1977-11-08
JPS49128725A (enrdf_load_stackoverflow) 1974-12-10
FR2237220B2 (enrdf_load_stackoverflow) 1977-03-04

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