EP0695968A2 - Réduction de la viscosité dans une composition photographique à l'état fondue - Google Patents

Réduction de la viscosité dans une composition photographique à l'état fondue Download PDF

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Publication number
EP0695968A2
EP0695968A2 EP95112023A EP95112023A EP0695968A2 EP 0695968 A2 EP0695968 A2 EP 0695968A2 EP 95112023 A EP95112023 A EP 95112023A EP 95112023 A EP95112023 A EP 95112023A EP 0695968 A2 EP0695968 A2 EP 0695968A2
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EP
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Prior art keywords
water
viscosity
cyclodextrin
solution
photographic
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Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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EP95112023A
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German (de)
English (en)
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EP0695968A3 (fr
Inventor
Ravi C/O Eastman Kodak Co. Sharma
Sharon Rose C/O Eastman Kodak Co. Girolmo
Gary William C/O Eastman Kodak Co. Visconte
Chris C/O Eastman Kodak Co. Gangemi
Edwin C/O Eastman Kodak Co. Garcia
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Eastman Kodak Co
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Eastman Kodak Co
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Publication of EP0695968A2 publication Critical patent/EP0695968A2/fr
Publication of EP0695968A3 publication Critical patent/EP0695968A3/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
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
    • G03C1/00—Photosensitive materials
    • G03C1/005—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein
    • G03C1/04—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein with macromolecular additives; with layer-forming substances

Definitions

  • This invention relates to a method for the preparation of a photographic element, and in particular to a method of controlling the viscosity of a photographic melt.
  • Photographic elements typically comprise a support having thereon at least one light-sensitive layer.
  • Color photographic elements typically comprise at least one layer sensitive to blue light, at least one layer sensitive to green light and at least one layer sensitive to red light.
  • a color photographic element also contains various other layers, such as subbing layers, interlayers, antihalation layers and the like. Each layer of a photographic element is applied, generally simultaneously with other layers, to an appropriate support in a coating process.
  • photographic coating compositions comprising emulsions, dispersions, and/or other photographic addenda for each layer are coated from aqueous solutions which contain a hydrophilic colloid, such as gelatin.
  • a hydrophilic colloid such as gelatin.
  • coating takes place at temperatures between about 35° to about 50°C.
  • the photographic emulsions and dispersions are prepared, chill-set and stored until needed for coating. At that time they are then heated to about 35° to about 50°C to melt the chill-set emulsion or dispersion to provide the fluid coating compositions which are frequently called “melts", "coating melts" or "photographic melts".
  • the second primary method is the curtain coating process.
  • photographic addenda such as masking couplers, oxidized developer scavengers, filter dyes, optical brighteners, ultraviolet radiation absorbers, dye transfer dyes, etc.
  • Such materials are usually fully water soluble, or are soluble to the extent of about 5-20% by weight, in water containing 5 to 20% by weight of a water miscible auxiliary solvent such as methanol, ethanol, propanol, isopropanol, acetone, methyl ethyl ketone, ethyl acetate, or the like.
  • a water miscible auxiliary solvent such as methanol, ethanol, propanol, isopropanol, acetone, methyl ethyl ketone, ethyl acetate, or the like.
  • Such materials behave also in a similar manner in the presence of a hydrophilic colloid.
  • amphiphilic addenda disclosed in the '435 patent are block oligomeric compounds comprising hydrophobic polyoxypropylene blocks (A) and hydrophilic polyoxyethylene blocks (B) joined in the manner of A-B-A, B-A-B, A-B, (A-B) n -G-(B-A), or (B-A) n -G-(A-B), where G is a connective organic moiety and n is between 1 and 3.
  • amphiphilic addenda examples include Ono et al. U.S. Patent No. 3,860,425 and in Visconte et al. US Patent 5,300,418.
  • An object of this invention is to reduce the high viscosity of photographic gelatin-containing melts, which contain an anionically charged, hydrophobic group-containing photographic addenda that are water soluble, or rendered water soluble by assistance of a water-miscible organic auxiliary solvent.
  • One aspect of this invention comprises an aqueous photographic coating composition
  • an aqueous photographic coating composition comprising an aqueous solution comprising gelatin and an anionically charged, hydrophobic group-containing compound that is (a) soluble in water or a mixture of water and a water-miscible organic solvent, and (b) which confers an undesirably high viscosity to aqueous gelatin solutions, wherein the composition further comprises a cyclodextrin in an amount sufficient to reduce the viscosity of the solution.
  • Another aspect of this invention comprises a photographic element comprising a support having thereon a layer comprising:
  • Another aspect of this invention is a method of reducing the viscosity of an aqueous gelatin solution containing an anionically charged, hydrophobic group-containing compound that is (a) soluble in water or a mixture of water and a water-miscible organic solvent, and (b) which confers an undesirably high viscosity to aqueous gelatin solutions, which method comprises adding to said solution a cyclodextrin in an amount sufficient to reduce the viscosity of the solution.
  • a further aspect of this invention is a method of reducing the viscosity of an aqueous gelatin solution containing an anionically charged, hydrophobic group-containing compound that is (a) soluble in water or a mixture of water and a water-miscible organic solvent, and (b) which confers an undesirably high viscosity to aqueous gelatin solutions, which method comprises adding to said solution a cyclodextrin in an amount sufficient to reduce the viscosity of the solution without reducing in the surface tension of the composition.
  • This invention enables one to adjust the viscosity of a photographic coating composition without using undesirably large amounts of water to dilute the composition or adding a nonionic surfactant, including sugar based surfactants, as taught by the prior art, which may reduce the surface tension of the composition and/or cause undesired sensitometric changes in the resulting photographic element.
  • Fig. 1 illustrates the physical configuration of a cyclodextrin molecule.
  • Fig. 2 is a graph showing the surface tension of an aqueous solution of the anionically charged, hydrophobic group-containing compound, SC-1, obtained as described in the examples provided below.
  • Fig. 3 is a graph showing shows the effect of adding ⁇ -cyclodextrin to an aqueous solution of SC-1, obtained as described in the examples provided below.
  • the invention is generally accomplished by providing a melt for coating of a layer of a photographic element and which contains a hydrophilic colloid and an anionically charged, hydrophobic group-containing compound that is (a) soluble in water or a mixture of water and a water-miscible organic solvent, and (b) which confers an undesirably high viscosity to aqueous gelatin solutions, and adding to the solution an amount of a cyclodextrin effective to reduce the viscosity of the solution.
  • Illustrative hydrophilic colloids include water-soluble polymers, gelatin, gelatin derivatives, cellulose esters, casein, agar, sodium alginate, starch, polyvinyl alcohol, polyacrylic acid copolymers and maleic anhydride copolymers and mixtures thereof.
  • the cellulose esters include hydroxyl propyl cellulose, carboxymethyl cellulose and hydroxyethyl cellulose.
  • the latex polymers include vinyl chloride copolymers, vinylidene chloride copolymers, acrylic ester copolymers, vinyl acetate copolymers and butadiene copolymers. Among them, gelatin is most preferred.
  • the amount of hydrophilic colloid in the solution is preferably about 2 to about 20 wt.%, based on the weight of the solution.
  • Illustrative anionically charged, anhydrophobic group-containing addenda include sodium dodecyl sulfate, sodium octyl sulfate, sodium decyl sulfate, sodium tetradecyl sulfate, sodium or potassium salt of octadecyl hydroquinone sulfate, or a compound of the formula:
  • the anionically charged hydrophobic group-containing compound is preferably present in the solution in an amount of from about 0.1 to about 10 wt.%, based on the weight of the solution.
  • the viscosity of the aqueous hydrophilic colloid solution is decreased by addition of a cyclodextrin.
  • Cyclodextrins are torus shaped cyclic oligosaccharides formed by the linking of 6, 7 or 8 glucopyranose units by a, (1-4) linkages (called ⁇ -, ⁇ - and ⁇ -cyclodextrin respectively). Cyclodextrins have the following structural formula: wherein n is as defined below.
  • a cyclodextrin molecule is shown as torus, 1, having a cavity 2, which has a diameter d.
  • Cyclodextrins can be thought of as "molecular buckets" as they are toroidal-shaped, rigid structures with a well-defined cavity as illustrated in Fig. 1.
  • cyclodextrins Due to the hydrophobic nature of the cavity, cyclodextrins are known to form various inclusion complexes in aqueous solutions and solid state with apolar (hydrophobic) molecules which fit into cyclodextrin's cavity without teh formation of a covalent bond. Further, polar compounds and certain inorganic ions have also been found to bind with cyclodextrin. (Takisawa, N.; Shirahama, K.; Tanaka, I. Colloid and Polymer Science 271(1993)499-503; Bender, K. L.; Komiyama, M. in Cyclodextrin Chemistry , Springer-Verlag, Berlin.; Saenger, W., Angew Chem. Int. Ed.
  • the cyclodextrin is added in an amount effective to reduce the viscosity of the melt.
  • the cyclodextrin is added to the melt preferably in an amount sufficient to provide a mole ratio of cyclodextrin to anionically charged, hydrophobic group-containing addenda of 1 to about 6, more preferably 1 to about 4 and most preferably about 3 to about 4.
  • the cyclodextrin is generally added after the photographic emulsion or dispersion has been heated to form a coating melt.
  • the viscosity of one layer of a multiple layer coating depends of the viscosities of the adjacent layers.
  • the photographic composition or melt of the invention can be used in any of the ways and in any of the combinations known in the art.
  • the invention materials are coated as a layer on a support to form part of a photographic element.
  • the photographic elements can be single color elements or multicolor elements.
  • Multicolor elements contain image dye-forming units sensitive to each of the three primary regions of the spectrum. Each unit can comprise a single emulsion layer or multiple emulsion layers sensitive to a given region of the spectrum.
  • the layers of the element, including the layers of the image-forming units can be arranged in various orders as known in the art.
  • the emulsions sensitive to each of the three primary regions of the spectrum can be disposed as a single segmented layer.
  • a typical multicolor photographic element comprises a support bearing a cyan dye image-forming unit comprised of at least one red-sensitive silver halide emulsion layer having associated therewith at least one cyan dye-forming coupler, a magenta dye image-forming unit comprising at least one green-sensitive silver halide emulsion layer having associated therewith at least one magenta dye-forming coupler, and a yellow dye image-forming unit comprising at least one blue-sensitive silver halide emulsion layer having associated therewith at least one yellow dye-forming coupler.
  • the element can contain additional layers, such as filter layers, interlayers, overcoat layers, subbing layers, and the like.
  • the photographic element can be used in conjunction with an applied magnetic layer as described in Research Disclosure , November 1992, Item 34390 published by Kenneth Mason Publications, Ltd., Dudley Annex, 12a North Street, Emsworth; Hampshire P010 7DQ, ENGLAND.
  • the silver halide emulsions employed in the elements of this invention can be either negative-working or positive-working. Suitable emulsions and their preparation as well as methods of chemical and spectral sensitization are described in Sections I through IV. Color materials and development modifiers are described in Sections V and XXI. Vehicles are described in Section IX, and various additives such as brighteners, antifoggants, stabilisers, light absorbing and scattering materials, hardeners, coating aids, plasticizers, lubricants and matting agents are described , for example, in Sections V, VI, VIII, X, XI, XII, and XVI. Manufacturing methods are described in Sections XIV and XV, other layers and supports in Sections XIII and XVII, processing methods and agents in Sections XIX and XX, and exposure alternatives in Section XVIII.
  • Coupling-off groups are well known in the art. Such groups can determine the chemical equivalency of a coupler, i.e., whether it is a 2-equivalent or a 4-equivalent coupler, or modify the reactivity of the coupler. Such groups can advantageously affect the layer in which the coupler is coated, or other layers in the photographic recording material, by performing, after release from the coupler, functions such as dye formation, dye hue adjustment, development acceleration or inhibition, bleach acceleration or inhibition, electron transfer facilitation, color correction and the like.
  • the presence of hydrogen at the coupling site provides a 4-equivalent coupler, and the presence of another coupling-off group usually provides a 2-equivalent coupler.
  • Representative classes of such coupling-off groups include, for example, chloro, alkoxy, aryloxy, hetero-oxy, sulfonyloxy, acyloxy, acyl, heterocyclyl, sulfonamido, mercaptotetrazole, benzothiazole, mercaptopropionic acid, phosphonyloxy, arylthio, and arylazo.
  • Image dye-forming couplers may be included in the element such as couplers that form cyan dyes upon reaction with oxidized color developing agents which are described in such representative patents and publications as: U.S. Pat. Nos. 2,772,162, 2,895,826, 3,002,836, 3,034,892, 2,474,293, 2,423,730, 2,367,531, 3,041,236, 4,883,746 and "Farbkuppler-eine LiteratureUbersicht,” published in Agfa Mitannonen, Band III, pp. 156-175 (1961).
  • couplers are phenols and naphthols that form cyan dyes on reaction with oxidized color developing agent.
  • Couplers that form magenta dyes upon reaction with oxidized color developing agent are described in such representative patents and publications as: U.S. Pat. Nos. 2,600,788, 2,369,489, 2,343,703, 2,311,082, 3,152,896, 3,519,429, 3,062,653, 2,908,573 and "Farbkuppler-eine LiteratureUbersicht,” published in Agfa Mitannonen, Band III, pp. 126-156 (1961).
  • couplers are pyrazolones, pyrazolotriazoles, or pyrazolobenzimidazoles that form magenta dyes upon reaction with oxidized color developing agents.
  • Couplers that form yellow dyes upon reaction with oxidized and color developing agent are described in such representative patents and publications as: U.S. Pat. Nos. 2,875,057, 2,407,210, 3,265,506, 2,298,443, 3,048,194, 3,447,928 and "Farbkuppler-eine LiteratureUbersicht,” published in Agfa Mitannonen, Band III, pp. 112-126 (1961).
  • Such couplers are typically open chain ketomethylene compounds.
  • couplers any of which may contain known ballasts or coupling-off groups such as those described in U.S. Patent 4,301,235; U.S. Patent 4,853,319 and U.S. Patent 4,351,897.
  • the coupler may also be used in association with "wrong" colored couplers (e.g. to adjust levels of interlayer correction) and, in color negative applications, with masking couplers such as those described in EP 213.490; Japanese Published Application 58-172,647; U.S. Patent 2,983,608; German Application DE 2,706,117C; U.K. Patent 1,530,272; Japanese Application A-113935; U.S. Patents 4,070,191 and 4,273,861; and German Application DE 2,643,965.
  • the masking couplers may be shifted or blocked.
  • the photographic element may also contain materials that accelerate or otherwise modify the processing steps e.g. of bleaching or fixing to improve the quality of the image.
  • Bleach accelerator releasing couplers such as those described in EP 193,389; EP 301,477; U.S. 4,163,669; U.S. 4,865,956; and U.S. 4,923,784, may be useful.
  • Also contemplated is use of the compositions in association with nucleating agents, development accelerators or their precursors (UK Patent 2,097,140; U.K. Patent 2,131,188); electron transfer agents (U.S. 4,859,578; U.S.
  • antifogging and anti color-mixing agents such as derivatives of hydroquinones; aminophenols, amines, gallic acid; catechol; ascorbic acid; hydrazides; sulfonamidophenols; and non color-forming couplers.
  • the materials of the invention may replace or supplement the materials of an element comprising a support bearing the following layers from top to bottom:
  • the photographic elemtns may comprise a support bearing the following layers from top to bottom:
  • the photographic element may comprise a support bearing the following layers from top to bottom:
  • the invention materials may also be used in combination with filter dye layers comprising colloidal silver sol or yellow, cyan, and/or magenta filter dyes, either as oil-in-water dispersions, latex dispersions or as solid particle dispersions. Additionally, they may be used with "smearing" couplers (e.g. as described in U.S. 4,366,237; EP 96,570; U.S. 4,420,556; and U.S. 4,543,323.) Also, the compositions may be blocked or coated in protected form as described, for example, in Japanese Application 61/258,249 or U.S. 5,019,492.
  • the photographic element may also contain image-modifying compounds such as "Developer Inhibitor-Releasing” compounds (DIR's).
  • DIR's useful in conjunction with the compositions of the invention are known in the art and examples are described in U.S. Patent Nos.
  • the concepts of the present invention may be employed to obtain reflection color prints as described in Research Disclosure , November 1979, Item 18716, available from Kenneth Mason Publications, Ltd, Dudley Annex, 12a North Street, Emsworth, Hampshire P0101 7DQ, England.
  • Materials of the invention may be coated on pH adjusted support as described in U.S. 4,917,994; with epoxy solvents (EP 0 164 961); with nickel complex stabilizers (U.S. 4,346,165; U.S. 4,540,653 and U.S. 4,906,559 for example); with ballasted chelating agents such as those in U.S.
  • the average useful ECD of photographic emulsions can range up to about 10 microns, although in practice emulsion ECD's seldom exceed about 4 microns. Since both photographic speed and granularity increase with increasing ECD's, it is generally preferred to employ the smallest tabular grain ECD's compatible with achieving aim speed requirements.
  • Emulsion tabularity increases markedly with reductions in tabular grain thickness. It is generally preferred that aim tabular grain projected areas be satisfied by thin (t ⁇ 0.2 micron) tabular grains. To achieve the lowest levels of granularity it is preferred that aim tabular grain projected areas be satisfied with ultrathin (t ⁇ 0.06 micron) tabular grains. Tabular grain thicknesses typically range down to about 0.02 micron. However, still lower tabular grain thicknesses are contemplated. For example, Daubendiek et al U.S. Patent 4,672,027 reports a 3 mole percent iodide tabular grain silver bromoiodide emulsion having a grain thickness of 0.017 micron.
  • tabular grains of less than the specified thickness account for at least 50 percent of the total grain projected area of the emulsion.
  • tabular grains satisfying the stated thickness criterion account for the highest conveniently attainable percentage of the total grain projected area of the emulsion.
  • tabular grains satisfying the stated thickness criteria above account for at least 70 percent of the total grain projected area.
  • tabular grains satisfying the thickness criteria above account for at least 90 percent of total grain projected area.
  • Suitable tabular grain emulsions can be selected from among a variety of conventional teachings, such as those of the following: Research Disclosure, Item 22534, January 1983, published by Kenneth Mason Publications, Ltd., Emsworth, Hampshire P010 7DD, England; U.S. Patent Nos.
  • the emulsions can be surface-sensitive emulsions, i.e., emulsions that form latent images primarily on the surfaces of the silver halide grains, or the emulsions can form internal latent images predominantly in the interior of the silver halide grains.
  • the emulsions can be negative-working emulsions, such as surface-sensitive emulsions or unfogged internal latent image-forming emulsions, or direct-positive emulsions of the unfogged, internal latent image-forming type, which are positive-working when development is conducted with uniform light exposure or in the presence of a nucleating agent.
  • Photographic elements can be exposed to actinic radiation, typically in the visible region of the spectrum, to form a latent image and can then be processed to form a visible dye image.
  • Processing to form a visible dye image includes the step of contacting the element with a color developing agent to reduce developable silver halide and oxidize the color developing agent. Oxidized color developing agent in turn reacts with the coupler to yield a dye.
  • the processing step described above provides a negative image.
  • the described elements can be processed in the known C-41 color process as described in The British Journal of Photography Annual of 1988, pages 191-198. Where applicable, the element may be processed in accordance with color print processes such a the RA-4 process of Eastman Kodak Company as described in the British Journal of Photography Annual of 1988, Pp 198-199.
  • the color development step can be preceded by development with a non-chromogenic developing agent to develop exposed silver halide, but not form dye, and followed by uniformly fogging the element to render unexposed silver halide developable.
  • a direct positive emulsion can be employed to obtain a positive image.
  • Preferred color developing agents are p-phenylenediamines such as: 4-amino-N,N-diethylaniline hydrochloride, 4-amino-3-methyl-N,N-diethylaniline hydrochloride, 4-amino-3-methyl-N-ethyl-N-( ⁇ -(methanesulfonamido) ethyl)aniline sesquisulfate hydrate, 4-amino-3-methyl-N-ethyl-N-( ⁇ -hydroxyethyl)aniline sulfate, 4-amino-3- ⁇ -(methanesulfonamido)ethyl-N,N-diethylaniline hydrochloride and 4-amino-N-ethyl-N-(2-methoxyethyl)-m-toluidine di-p-toluene sulfonic acid.
  • Development is usually followed by the conventional steps of bleaching, fixing, or bleach-fixing, to remove silver or silver halide, washing, and drying.
  • any reference to a substituent by the identification of a group containing a substitutable hydrogen e.g. alkyl, amine, aryl, alkoxy, heterocyclic, etc.
  • a substitutable hydrogen e.g. alkyl, amine, aryl, alkoxy, heterocyclic, etc.
  • the substituent will have less than 30 carbon atoms and typically less than 20 carbon atoms.
  • Example 1 illustrates the reduction of viscosities of a coating melts by the addition of cyclodextrins.
  • Example 1 is a melt that has no SC-1, and shows the aqueous gelatin solution containing 10.1 wt.% gelatin has a viscosity of 23.1 cP RBT (Rolling Ball Time). Incorporation of SC-1 (0.21 wt %, based on the weight of the solution) in the melt raises the viscosity to 44.5 cP. However, it is seen that the addition of the compound ⁇ -cyclodextrin hydrate (commercially available from Aldrich Chemical Company) to the melt in progressively greater amounts, reduces the viscosity of the melts (Example 3, 4 and 5) to virtually the value of that of the melt that has no (SC-1).
  • SC-1 Rolling Ball Time
  • Fig. 3 it can be seen that the addition of increasing amounts of SC-1 to an aqueous solution of ⁇ -cyclodextrin (10 ⁇ 3 M), results in a drop in surface tension only after the molar amount of SC-1 approaches the number of moles of ⁇ -cyclodextrin. Assuming a 1:1 type association, the binding constant is about 990 M ⁇ 1.

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EP95112023A 1994-08-01 1995-07-31 Réduction de la viscosité dans une composition photographique à l'état fondue Withdrawn EP0695968A3 (fr)

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US28397894A 1994-08-01 1994-08-01
US283978 1994-08-01

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2332952A (en) * 1997-12-30 1999-07-07 Eastman Kodak Co Reduced viscosity gelatin mixture used in a process for making a direct dispersion of a photographically useful material
US6203973B1 (en) 1999-03-25 2001-03-20 Eastman Kodak Company Polymer latexes with core-shell morphology
CN109331784A (zh) * 2018-11-12 2019-02-15 中国石油大学(华东) 一种用于脱除水中有机污染物的一取代β-环糊精衍生物及其制备与使用方法

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GB2332952A (en) * 1997-12-30 1999-07-07 Eastman Kodak Co Reduced viscosity gelatin mixture used in a process for making a direct dispersion of a photographically useful material
US5998120A (en) * 1997-12-30 1999-12-07 Eastman Kodak Company Process for making a direct dispersion of a photographically useful material
GB2332952B (en) * 1997-12-30 2001-08-22 Eastman Kodak Co Process for making a direct dispersion of a photographically useful material
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CN109331784A (zh) * 2018-11-12 2019-02-15 中国石油大学(华东) 一种用于脱除水中有机污染物的一取代β-环糊精衍生物及其制备与使用方法
CN109331784B (zh) * 2018-11-12 2021-06-11 中国石油大学(华东) 一种用于脱除水中有机污染物的一取代β-环糊精衍生物及其制备与使用方法

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JPH08101477A (ja) 1996-04-16

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