US3676147A - Method of spectrally sensitizing photographic silver halide emulsions - Google Patents

Method of spectrally sensitizing photographic silver halide emulsions Download PDF

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US3676147A
US3676147A US880944A US3676147DA US3676147A US 3676147 A US3676147 A US 3676147A US 880944 A US880944 A US 880944A US 3676147D A US3676147D A US 3676147DA US 3676147 A US3676147 A US 3676147A
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dye
silver halide
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Simone J Boyer
Roger Caridi
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Eastman Kodak Co
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Eastman Kodak Co
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    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
    • G03C1/00—Photosensitive materials
    • G03C1/005—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein
    • G03C1/06—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein with non-macromolecular additives
    • G03C1/08—Sensitivity-increasing substances
    • G03C1/10—Organic substances
    • G03C1/102—Organic substances dyes other than methine dyes

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  • This invention relates to novel photographic processes and more particularly to novel processes for spectrally sensitizing photographic silver halide emulsions. It also relates to novel photographic materials and processes.
  • the conventional method of sensitizing light sensitive silver halide consists of dissolving the sensitizing dye in an appropriate organic solvent, such as methyl alcohol, ethyl alcohol, acetone, etc., and adding the resulting solution to a liquid photographic silver halide emulsion. While this general method has provided a commercially feasible means for incorporating sensitizing dyes into silver halide emulsions, it still requires considerable care and extra manipulative steps in adjusting the volume of solvent to quantities that are compatible with the particular emulsion and still produce the desired results. Also, it is well known that excessive solvent engenders disadvantageous diffusion or wandering of the sensitizing dyes in the emulsions.
  • an object of this invention to provide a new method for spectrally sensitizing light sensitive silver halide.
  • Another object of this invention is to provide novel dispersions of spectral sensitizing dye.
  • a process for spectrally sensitizing photographic silver halide which comprises: dispersing a substantially water-insoluble photographic spectral sensitizing dye into a water-soluble organic liquid without dissolving the dye; and, incorporating the dispersion into a liquid photographic silver halide emulsion.
  • novel dye dispersions comprise undissolved particles of a photographic spectral sensitizing dye in a water-soluble organic liquid.
  • compositions which comprise a hydrophilic colloid containing undissolved particles of photographic spectral sensitizing dye in a water-soluble organic liquid in which said dye is substantially insoluble.
  • Such composition can be either liquid or solid; either form is useful for spectrally sensitizing liquid photographic silver halide emulsions.
  • the dye dispersions of the invention are especially useful in coating processes which require low amounts of organic solvent.
  • the dye dispersions are stable and can be conveniently stored or transported.
  • compositions of dye in organic liquid can be prepared in any convenient manner. Ball milling the dye and organic liquid gives highly satisfactory results. Ad-
  • the liquid contains dye particles which have an average diameter of up to about 1.0 micron.
  • Organic liquids which can be used in the practice of this invention are water-soluble materials, and are liquids below about 30 C.
  • Organic liquids can be used which are not solvents for the photographic sensitizing dye that is being used.
  • Such organic liquids are oily materials. They should not have any adverse effects on the photographic emulsion in which they are incorporated.
  • organic liquids which are solvents for the dye.
  • Such organic liquids e.g., methanol, ethanol or isopropanol are used at sufficiently low levels, compared to the quantity of dye, that only very small amounts of dye are dissolved. Both types of liquids function to separate, or prevent agglomeration of the dye particles. Such separation is essential to eflective spectral sensitization.
  • Typical organic liquids that are not dye solvents which can be used in the invention are represented by the following formula:
  • R represents a hydrogen atom or a lower alkyl group containing 1 to 4 carbon atoms, e.g., methyl, ethyl, butyl, etc.; R represents a hydrogen atom or a methyl group; R represents a hydrogen atom, an alkyl group containing from 1 to 3 carbon atoms, e.g., methyl, ethyl, propyl or isopropyl, a hydroxymethyl group or an acetoxymethyl group; and R represents a divalent alkylene group containing from 1 to 4 carbon atoms, e.g., -CH a)s 2)2, 2)3 0T and wherein the sum of the carbon atoms in said R R and R is a positive integer of from 1 to 4.
  • Typical useful liquids embraced by Formula I above include glycerol, monoacetin, ethylene glycol, methylglycol, (monomethyl ether of ethylene glycol), ethyl glycol ether, propyl glycol ether, butyl glycol ether, 1,3-propylene glycol, 1,3-butylene glycol, 1,4-butylene glycol, 2,3-butylene glycol, isobutylene glycol (Z-methyl-1,2-propanediol), 2-methyl-2, 3-butanediol, 3-methyl-l,3-butanediol, 1,2-pentanediol, l, 4-pentanediol, 2,3-pentanediol, 1,5-pentanediol, etc.
  • Glycerol and methylglycol are the preferred solvents herein.
  • organic liquids which are solvents for spectral sensitizing dyes. Such liquids are used in sufiiciently small amounts, relative to the quantity of spectral sensitizing dye, that no substantial amounts of dye are dissolved. Preferably, such liquids have a dissolving power for the dyes of less than 10 grams of dye per liter of solvent at 20 C.
  • Useful organic liquids of this class include alcohols having from 1 to 4 carbon atoms, such as methanol, ethanol, n-propanol, iso-propanol, n-butanol, iso-butanol or tert butanol; acetone; and, dimethylformamide. Such solvents provide less tacky dye dispersions than similar dispersions made with relatively high boiling organic liquids.
  • a typical useful solvent mixture of this type is a mixture of methanol (which is a solvent for most sensitizing dyes) together with glycerol (which is a non-solvent for most sensitizing dyes).
  • a typical useful solvent mixture of this type is a mixture of methanol (which is a solvent for most sensitizing dyes) together with glycerol (which is a non-solvent for most sensitizing dyes).
  • an organic liquid mixture comprising about to 95 parts by weight solvent (e.g., methanol) and 20 to 5 parts by weight of a non-solvent liquid (e.g., glycerol) and preferably about parts by Weight solvent and 10 parts by weight non-solvent.
  • the spectral sensitizing dye is dispersed in the organic liquid without dissolving the dye.
  • the term without dissolving the dye means that no substantial amount of dye is dissolved. Preferably, less than about by weight of the total dye mixed with the liquid is dissolved. Essentially no dye is dissolved when the dye is insoluble in the organic liquid.
  • the solvent is used in such small concentrations relative to the total amount of dye that no substantial amount of dye is dissolved.
  • Typical solutions of sensitizing dye in organic solvent e.g., methanol, contain about 1 to 3 grams dye per liter of solvent. In accordance with this invention, preferably about 5 to 20 cc. of solvent are used per gram of dye.
  • This invention can be practiced with any of the photographic spectral sensitizing dyes.
  • the invention is especially useful with the dyes that are substantially insoluble in aqueous solutions, e.g., dyes which have a solubility in water (at 20 C.) of less than about 1%.
  • Typical dyes which can be used in the practice of this invention are described in the following patents, the disclosure of which are incorporated herein by reference.
  • I, II, III and V include not only the specified iodide and bromide salts, but also the chloride, sulfamate, thiocyanate, perchlorate, ptoluenesulfonate, methyl sulfate, etc. salts. Also, Dye N0. XI includes any of the alkali metal salts such as lithium, potassium, etc.
  • the weight proportions of the water-soluble liquid (which is a non-solvent for the dyes) to dye can vary over a wide range, such as from about :5 to 100 150, but preferably from about 100:10 to 100240, respectively.
  • Liquids which are dye solvents are advantageously used in weight proportions of about 5 to 20 parts solvent per each part by weight of dye.
  • dispersions of the invention containing a binder such as gelatin can vary widely in the proportions of dye to gelatin, but the best results for sensitizing purposes are obtained with compositions wherein the dye varies from 20 to 40%, based on the total weight of dye plus binder.
  • the dispersions of the dyes can also contain two or more dyes in each dispersion or dispersions containing a single dye can also be used in combinations of two or more such dispersions.
  • the concentration of dye incorporated into the emulsions by the method of the invention for optimum sensitivity varies depending on the dye and emulsion about from 0.20 to 4.0 grams of dye per mole of silver halide in the emulsion.
  • the dye dispersions of the invention can be readily incorporated into the emulsions by any suitable method such as mixing, mechanical blending, etc.
  • compositions of the invention consisting essentially of organic liquid and dye can be added directly to liquid photographic silver halide emulsions to obtain good spectral sensitization.
  • the composition of the invention can be dispersed in a hydrophilic colloid.
  • the dispersion of dye-organic liquid in hydrophilic colloid can be used in liquid or solid form to sensitize liquid silver halide emulsions.
  • the hydrophilic colloid used with the dye-organic liquid can be any colloid which is compatible with the photographic emulsions, such as any of the hydrophilic colloids referred to below. Gelatin is especially useful.
  • the colloid is preferably free from silver halide, or, the mixture comprises a substantial amount of dye which is unadsorbed on any silver halide present in the colloid.
  • the light sensitive silver halide can be dispersed in any hydrophilic colloid (binder) that is satisfactory for dispersing silver halides, for example, gelatin, albumin, agar-agar, gum arabic, alginic acid, polyvinyl alcohol, polyvinyl pyrrolidone, cellulose ethers, partially hydrolyzed cellulose acetate, and the like.
  • the hydrophilic colloid can also contain dispersed polymerized vinyl compounds, such as those disclosed in U.S. Pats.
  • 3,142,568; 3,193,386; 3,062,674 and 3,220,844 and include the water insoluble polymers of alkyl acrylates and methacrylates, acrylic acid, sulfoalkyl acrylates or methacrylates and the like.
  • silver bromoiodide emulsions While the examples herein are illustrated with silver bromoiodide emulsions, it will be apparent that other silver halide emulsions such as silver chloride, silver bromide, silver chlorobromide, silver chlorobromoiodide, etc. can also be efliciently sensitized in like manner with the novel dye dispersions of the invention.
  • the emulsions prepared in accordance with the invention may be coated on any suitable photographic support such as cellulose acetate, cellulose acetate butyrate, polyesters such as poly(ethylene terephthalate), polyethylene,
  • the photographic emulsions prepared in accordance with the novel method of this invention may contain such addenda as chemical sensitizers, e.g., sulfur sensitizers (e.g., allyl thiocarbamate, thiourea, allylisothiocyanate, cystine, etc.), various gold compounds (e.g., potassium chloroaurate, auric trichloride, etc. (see Baldsiefen, U.S. Pat. No. 2,540,085, issued Feb. 6, 1951; Damschroder, U.S. Pat. No. 2,597,856, issued May 27, 1952 and Yutzy et a1.
  • chemical sensitizers e.g., sulfur sensitizers (e.g., allyl thiocarbamate, thiourea, allylisothiocyanate, cystine, etc.)
  • gold compounds e.g., potassium chloroaurate, auric trichloride, etc.
  • the silver halide emulsions of the invention can be hardened with any suitable hardener, including aldehyde hardeners such as formaldehyde, and mucochloric acid, aziridine hardeners, hardeners which are derivatives of dioxane, oxypolysaccharides such as oxy starch or oxy plant gums, and the like.
  • aldehyde hardeners such as formaldehyde, and mucochloric acid
  • aziridine hardeners hardeners which are derivatives of dioxane, oxypolysaccharides such as oxy starch or oxy plant gums, and the like.
  • the emulsion layers can also contain additional additives, particularly those known to be beneficial in photographic emulsions, including, for example, lubricating materials, stabilizers, speed increasing materials, absorbing dyes, plasticizers, and the like. These photographic emulsions can also contain in some cases additional spectral sensitizing dyes. Furthermore, these emulsions can contain color forming couplers or can be developed in solutions containing couplers or other color generating materials.
  • the useful color formers are the monomeric and polymeric color formers, e.g., pyrazolone color formers, as well as phenolic, heterocyclic and open chain couplers having a reactive methylene group.
  • the color forming couplers can be incorporated into the photographic silver halide emulsion using any suitable technique, e.g., techniques of the type shown in Jelley et al. U.S. Pat. 2,322,027, issued June 15, 1943, Fierke et al. U.S. Pat. 2,801,171, issued July 30, 1957, Fisher U.S. Pats. 1,055,155 and 1,102,028, issued Mar. 4, 1913 and June 30, 1914, respectively, and Wilmanns U.S. Pat. 2,186,849, issued Jan. 9, 1940. They can also be developed using incorporated developers such as polyhydroxybenzenes, aminophenols, 3 pyrazolidones, and the like.
  • EXAMPLE 1 1.350 g. of Dye No. I are milled for 6 hours in a ballmill with 6 cc. of methylglycol to give a dye dispersion wherein the dye particles have an average diameter less than about 1 micron. To this dispersion 18 g. of a gelatin solution are then added. The mixture is homogenized in a ball-mill for 15 minutes. The mixture is then air dried, formed into flakes so as to be readily bottled and stored at room temperature in a brown glass bottle. A suitable sample of the mixture is used to determine the dye content of the mixture. In the present example, the dye concentration is 31.5% by weight.
  • Each of these two emulsions is kept at 40 C. for 20 minutes and then each is coated onto a separate cellulose acetate film support.
  • the coated samples are sensitometrically tested by successive exposures of each sample to white light and through Wratten Filters No. 25 which transmits light at wavelengths longer than about 590 nm., No. 47 which transmits light in the region of about from 350 to 530 nm., and No. 58 which transmits light in the region of about from 470 to 615 nm., followed by development for about 6 minutes at room temperature in Kodak D-19 developer which has the following composition:
  • EXAMPLE 13 The photographic tests carried out in this example are similar to those described in above Example 12, except that the preparation of the milled dyes dispersed in gelatin were made 3 months before.
  • EXAMPLE 14 A negative silver halide emulsion similar to that described in above Example 12 is optically sensitized with the dye mixture:
  • EXAMPLE 15 A mixture of Dye Nos. I, II an III, in the proportions given in above Example 12, is milled with 10 cc. of methyl glycol until the dye particles have an average diameter less than about 1 micron. The resulting dye paste is dispersed in 12 g. of a 15% aqueous gelatin solution, dried and then used to sensitize a photographic silver halide emulsion, as described in Example 12. The sensitivity of this emulsion is substantially the same as that of the emulsion prepared in Example 12 by method (a), except that the speed loss in white light as compared to the control is 0.08 log E.
  • EXAMPLE 16 This example is identical with that of Example 15, except that the mixture of dyes is milled with 12 cc. of glycerol and taken up with 20 g. of a 10% aqueous gelatin solution.
  • the sensitometric results of this example are identical with those of above Example 15.
  • EXAMPLE 17 The mixture of dyes described in Example 14 is milled with 10 cc. of methylglycol, taken up with 30 g. of 10% gelatin solution and dried. The dry mixture is used for optically sensitizing a photographic emulsion by the method described in Example 12.
  • the emulsion sensitized with the solid mixture shows a speed loss of 0.10 log E as compared to the control (method a), in white light.
  • EXAMPLE 18 This example and results thereof are identical with those of Example 17, except that the dye mixture is milled with 15 cc. of glycerin.
  • EXAMPLE 19 500 mg. of Dye II are milled for 24 hours in a ballmill in the presence of cc. of methanol. Less than 5% by Weight of the total amount of dye is dissolved in methanol. 50 cc. of a aqueous gelatin solution are then added and the mixture is effected in the same ballmill at 40 C. for 2 hours.
  • This mixture is coated on unsubbed poly(ethylene terephthalate) support, in the form of a film having a thickness of 30,11. to 40 After drying, the film which adheres to the support due to the effect of electrostatic charges is readily stripped from the base. It is broken into flakes by being passed through a grate under the action of compressed air. It is then readily weighed, titrated and stored.
  • the mixture which contains about 8% by weight of dye, is used to spectrally sensitize an emulsion as described in Example 12.
  • the spectral sensitometric results obtained, as in Example 12, are identical with those obtained by conventional spectral sensitization methods (i.e., when the dye is dissolved in an aqueous solution of methanol and added to the emulsion).
  • EXAMPLE 20 The procedure of Example 19 is repeated except that the 5 cc. of methanol are replaced with 5 cc. of a 90:10 methanol-glycerin mixture. Identical sensitometric results are obtained.
  • any other of the dyes mentioned in Table 1 above, as well as still other known cyanine sensitizing dyes that are Waterinsoluble, can be substituted in the procedures of the above examples to give generally similar useful results.
  • any other of the mentioned water-soluble dihydroxyalkanes or lower monoalkyl ether derivatives thereof which are non-solvents for the sensitizing dyes glycerol, monoacetin, ethylene glycol, methylglycol, ethyl glycol ether, propyl glycol ether, butyl glycol ether, 1,3-propylene glycol, 1,3-butylene glycol, 1,4-butylene glycol, 2,3-butylene glycol, isobutylene glycol, 2-methyl-2,3-butanediol, 3- methyl-1,3-butanediol, 1,2-pentanediol, 1,4-pentanediol, 2,3-pentaned
  • a process for spectrally sensitizing photographic silver halide which comprises: dispersing a substantially water-insoluble photographic spectral sensitizing dye in a water-soluble organic liquid which is a non-solvent for said dye; and, incorporating said dispersion into a liquid photographic silver halide emulsion, said organic liquid having the following formula:
  • R represents a member selected from the group consisting of a hydrogen atom and an alkyl group containing from 1 to 4 carbon atoms
  • R represents a member selected from the group consisting of a hydrogen atom and a methyl group
  • R represents a member selected from the group consisting of a hydrogen atom, an alkyl group containing from 1 to 3 carbon atoms, a hydroxy-alkyl group of from 1 to 3 carbon atoms and an acetoxymethyl group
  • R represents a divalent alkylene group containing from '1 to 4 carbon atoms, the sum of the carbon atoms in said R R and R being from 1 to 4.
  • the process for spectrally sensitizing silver halide which comprises: dispersing a substantially water-insoluble photographic spectral sensitizing dye in an organic liquid selected from the group consisting of glycerol, monoacetin, ethylene glycol, methylglycol, ethyl glycol ether, propyl glycol ether, butyl glycol ether, 1,3-propylene glycol, 1,3-butylene glycol, 1,4-butylene glycol, 2,3- butylene glycol, isobutylene glycol, 2-methyl-2,3-butanediol, 3-methyl-1,3butanediol, 1,2-pentanediol, 1,4-pentanediol, 2,3-pentanediol, and 1,5-pentanediol; and, incorporating said dispersion into a liquid photographic silver halide emulsion to spectrally sensitize the silver halide.
  • an organic liquid selected from
  • the dispersion of dye in organic liquid is mixed with an aqueous solution of a hydrophilic colloid to form a homogenous mixture and said mixture is incorporated into the light-sensitive silver halide emulsion.
  • a process for spectrally sensitizing photographic silver halide which comprises: dispersing in methylglycol a photographic spectral sensitizing dye selected from the group consisting of 1'ethyl-2-methylthia-4'-cyanine salt;
  • a process for spectrally sensitizing photographic silver halide which comprises: dispersing in glycerol a photographic spectral sensitizing dye selected from the group consisting of 1'-ethyl-2-methylthia-4'-cyanine salt;
  • a process for spectrally sensitizing photographic silver halide which comprises: dispersing a substantially water-insoluble photographic spectral sensitizing dye in a water-soluble organic liquid mixture without dissolving the dye, said organic liquid mixture comprising about to parts by weight of an organic liquid selected from the group consisting of an alcohol having from 1 to 4 carbon atoms, acetone and dimethylformamide, and, about 20 to 5 parts by weight of an organic liquid having the following formula:
  • R represents a member selected from the group consisting of a hydrogen atom and an alkyl group containing from 1 to 4 carbon atoms
  • R represents a member selected from the group consisting of a hydrogen atom and a methyl group
  • R represents a member selected from the group consisting of a hydrogen atom, an alkyl group containing from 1 to 3 carbon atoms, a hydroxyalkyl group of from 1 to 3 carbon atoms and an acetoxymethyl group
  • R represents a divalent alkylene group containing from 1 to 4 carbon atoms, the sum of the carbon atoms in said R R and R being from 1 to 4; and, incorporating said dispersion into a liquid photographic silver halide emulsion to spectrally sensitize the silver halide.
  • a process as defined in claim 9 wherein said organic liquid mixture comprises about 80 to 95 parts by weight methanol and about 20 to 5 parts by weight glycerol.
  • a process for spectrally sensitizing silver halide which comprises: dispersing, in about 5 cc. of an organic liquid mixture comprising 9 parts by weight methanol and 1 part by weight glycerol, about .5 gram of 3-ethyl-5-[(3- ethyl 2(3H) benzothiazolylidene)isopropylidene] 2- thio-2,4-oxazolidinedione.
  • a mixture comprising a hydrophilic colloid and a dispersion of a photographic spectral sensitizing dye in a water-soluble organic liquid in which the dye is insoluble, said organic liquid having the following formula:
  • R represents a member selected from the group consisting of a hydrogen atom and an alkyl group containing from 1 to 4 carbon atoms
  • R represents a member selected from the group consisting of a hydrogen atom and a methyl group
  • R represents a member selected from the group consisting of a hydrogen atom, an alkyl group containing from 1 to 3 carbon atoms, a hydroxyalkyl group of from 1 to 3 carbon atoms and an acetoxymethyl group
  • R represents a divalent alkylene group containing from 1 to 4 carbon atoms, the sum of the carbon atoms in said R R and R being from 1 to 4.
  • a mixture comprising a hydrophilic colloid and a dispersion as defined in claim 12 wherein said organic liquid is selected from the group consisting of glycerol, monoacetin, ethylene glycol, methylglycol, ethyl glycol ether propyl glycol ether, butyl glycol ether, 1,3-propylene glycol, 1,3-butylene glycol, 1,4 butylene glycol, 2,3-butylene glycol, isobutylene glycol, 2-methyl-2,3-butanediol, 3- methyl 1,3-butanediol, 1,2-pentanediol, 1,4-pentanediol, 2,3-pentanediol and 1,5-pentanediol.
  • said organic liquid is selected from the group consisting of glycerol, monoacetin, ethylene glycol, methylglycol, ethyl glycol ether propyl glycol ether, butyl

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US880944A 1968-12-24 1969-11-28 Method of spectrally sensitizing photographic silver halide emulsions Expired - Lifetime US3676147A (en)

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Cited By (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3769011A (en) * 1972-01-26 1973-10-30 Eastman Kodak Co Photoconductive compositions and elements containing methine dye in j-aggregate state
US4004928A (en) * 1974-08-28 1977-01-25 Mitsubishi Paper Mills, Ltd. Color photographic material
US4006025A (en) * 1975-06-06 1977-02-01 Polaroid Corporation Process for dispersing sensitizing dyes
US4140530A (en) * 1977-02-18 1979-02-20 Ciba-Geigy Ag Preparation of photographic material
US4146399A (en) * 1977-02-18 1979-03-27 Ciba-Geigy Ag Preparation of photographic material
US4193801A (en) * 1976-07-29 1980-03-18 Ciba-Geigy Aktiengesellschaft Process for producing photographic silver halide material
EP0124795A2 (en) 1983-04-11 1984-11-14 Fuji Photo Film Co., Ltd. Silver halide photographic emulsion
US5238797A (en) * 1991-08-26 1993-08-24 Konica Corporation Silver halide color photographic light-sensitive material containing a 1-pentahalogenophenyl-substituted 5-pyrazolone colored magenta coupler
US5302506A (en) * 1991-06-26 1994-04-12 Konica Corporation Silver halide photographic materials
US5360695A (en) * 1993-01-26 1994-11-01 Eastman Kodak Company Aqueous developable dye diffusion transfer elements containing solid particle thermal solvent dispersions
US5401623A (en) * 1992-10-05 1995-03-28 Eastman Kodak Company Reactivity control in microcrystalline coupler dispersions
US5460937A (en) * 1993-10-20 1995-10-24 Eastman Kodak Company Process for incorporating a hydrophobic compound into an aqueous medium
US5512414A (en) * 1993-09-23 1996-04-30 Eastman Kodak Company Solid particle coupler dispersions for color diffusion transfer elements
US5580711A (en) * 1993-03-02 1996-12-03 Konica Corporation Silver halide photographic light-sensitive material
US5582957A (en) * 1995-03-28 1996-12-10 Eastman Kodak Company Resuspension optimization for photographic nanosuspensions
US5609998A (en) * 1994-12-29 1997-03-11 Eastman Kodak Company Process for dispersing concentrated aqueous slurries
EP0762193A1 (en) * 1995-08-31 1997-03-12 Eastman Kodak Company Nonaqueous solid particle dye dispersions
US5723255A (en) * 1995-06-07 1998-03-03 Eastman Kodak Company Nanoparticulate thermal solvents
US5994041A (en) * 1985-04-06 1999-11-30 Eastman Kodak Company Process for buffering concentrated aqueous slurries

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JP3508081B2 (ja) 1995-10-30 2004-03-22 コニカミノルタホールディングス株式会社 ハロゲン化銀写真感光材料用固体処理剤および処理方法

Cited By (23)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3769011A (en) * 1972-01-26 1973-10-30 Eastman Kodak Co Photoconductive compositions and elements containing methine dye in j-aggregate state
US4004928A (en) * 1974-08-28 1977-01-25 Mitsubishi Paper Mills, Ltd. Color photographic material
US4006025A (en) * 1975-06-06 1977-02-01 Polaroid Corporation Process for dispersing sensitizing dyes
US4193801A (en) * 1976-07-29 1980-03-18 Ciba-Geigy Aktiengesellschaft Process for producing photographic silver halide material
US4140530A (en) * 1977-02-18 1979-02-20 Ciba-Geigy Ag Preparation of photographic material
US4146399A (en) * 1977-02-18 1979-03-27 Ciba-Geigy Ag Preparation of photographic material
EP0124795A2 (en) 1983-04-11 1984-11-14 Fuji Photo Film Co., Ltd. Silver halide photographic emulsion
US5994041A (en) * 1985-04-06 1999-11-30 Eastman Kodak Company Process for buffering concentrated aqueous slurries
US5302506A (en) * 1991-06-26 1994-04-12 Konica Corporation Silver halide photographic materials
US5238797A (en) * 1991-08-26 1993-08-24 Konica Corporation Silver halide color photographic light-sensitive material containing a 1-pentahalogenophenyl-substituted 5-pyrazolone colored magenta coupler
US5401623A (en) * 1992-10-05 1995-03-28 Eastman Kodak Company Reactivity control in microcrystalline coupler dispersions
US5434036A (en) * 1992-10-05 1995-07-18 Eastman Kodak Company Process for forming microcrystalline coupler dispersions
US5494775A (en) * 1993-01-26 1996-02-27 Eastman Kodak Company Heat image separation with solid particle thermal solvent dispersions
US5360695A (en) * 1993-01-26 1994-11-01 Eastman Kodak Company Aqueous developable dye diffusion transfer elements containing solid particle thermal solvent dispersions
US5580711A (en) * 1993-03-02 1996-12-03 Konica Corporation Silver halide photographic light-sensitive material
US5512414A (en) * 1993-09-23 1996-04-30 Eastman Kodak Company Solid particle coupler dispersions for color diffusion transfer elements
US5460937A (en) * 1993-10-20 1995-10-24 Eastman Kodak Company Process for incorporating a hydrophobic compound into an aqueous medium
US5609998A (en) * 1994-12-29 1997-03-11 Eastman Kodak Company Process for dispersing concentrated aqueous slurries
US5750321A (en) * 1994-12-29 1998-05-12 Eastman Kodak Company Process for buffering concentrated aqueous slurries
US5582957A (en) * 1995-03-28 1996-12-10 Eastman Kodak Company Resuspension optimization for photographic nanosuspensions
US5723255A (en) * 1995-06-07 1998-03-03 Eastman Kodak Company Nanoparticulate thermal solvents
EP0762193A1 (en) * 1995-08-31 1997-03-12 Eastman Kodak Company Nonaqueous solid particle dye dispersions
US5709983A (en) * 1995-08-31 1998-01-20 Eastman Kodak Company Nonaqueous solid particle dye dispersions

Also Published As

Publication number Publication date
GB1271329A (en) 1972-04-19
BE742612A (enrdf_load_stackoverflow) 1970-05-14
CA942565A (en) 1974-02-26
DE1964169A1 (de) 1970-07-09
FR1602224A (enrdf_load_stackoverflow) 1970-10-26
BR6915565D0 (pt) 1973-01-18

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