EP0049399A2 - Procédé de fabrication de dispersions d'agents de copulation hydrophobes dans l'eau ainsi que l'utilisation de ces dispersions dans la fabrication de matériaux de reproduction sensibles à la lumière - Google Patents

Procédé de fabrication de dispersions d'agents de copulation hydrophobes dans l'eau ainsi que l'utilisation de ces dispersions dans la fabrication de matériaux de reproduction sensibles à la lumière Download PDF

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Publication number
EP0049399A2
EP0049399A2 EP81107366A EP81107366A EP0049399A2 EP 0049399 A2 EP0049399 A2 EP 0049399A2 EP 81107366 A EP81107366 A EP 81107366A EP 81107366 A EP81107366 A EP 81107366A EP 0049399 A2 EP0049399 A2 EP 0049399A2
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EP
European Patent Office
Prior art keywords
dispersions
water
acid
dispersion
coupler
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Granted
Application number
EP81107366A
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German (de)
English (en)
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EP0049399B1 (fr
EP0049399A3 (en
Inventor
Günter Dr. Helling
Helmut Dr. Reiff
Wolfgang Dr. Himmelmann
Günter Dr. Renner
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Agfa Gevaert AG
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Agfa Gevaert AG
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Publication date
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Publication of EP0049399A2 publication Critical patent/EP0049399A2/fr
Publication of EP0049399A3 publication Critical patent/EP0049399A3/de
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Publication of EP0049399B1 publication Critical patent/EP0049399B1/fr
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Classifications

    • 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
    • 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
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
    • G03C7/00—Multicolour photographic processes or agents therefor; Regeneration of such processing agents; Photosensitive materials for multicolour processes
    • G03C7/30—Colour processes using colour-coupling substances; Materials therefor; Preparing or processing such materials
    • G03C7/388—Processes for the incorporation in the emulsion of substances liberating photographically active agents or colour-coupling substances; Solvents therefor
    • G03C7/3882—Processes for the incorporation in the emulsion of substances liberating photographically active agents or colour-coupling substances; Solvents therefor characterised by the use of a specific polymer or latex

Definitions

  • the invention relates to a method for producing dispersions of hydrophobic substances with the aid of ionomeric polyaddition and / or polycondensation products, and to the use of such dispersions for producing light-sensitive recording layers.
  • DE-OS 1 812 578 From DE-OS 1 812 578 it is known to dissolve color couplers in an emulsion copolymer of styrene / butadiene, acrylonitrile / butadiene or vinyl chloride / vinylidene chloride and to add this solution to a photographic emulsion.
  • DE-OS 2 541 230 relates to a method for loading polymer particles, which are in the form of a polymer latex, with hydrophobic substances by mixing the latex with a solution of the hydrophobic substance in a water-miscible solvent.
  • DE-AS 2 54 1 274 synthetic latices are loaded with a hydrophobic substance by adding an aqueous latex to a solution of the hydrophobic substance in a water-miscible organic solvent or solvent mixture and then the organic solvent or solvent mixture removed from the latex.
  • DE-OS 2 835 856 describes the preparation of a latex loaded with a hydrophobic substance by mixing the substance dissolved in a water-miscible organic solvent with the latex. All these processes have in common that the hydrophobic substances are introduced into an aqueous polymer dispersion.
  • a disadvantage of this procedure is that the resulting loaded or impregnated dispersions lose stability due to the exposure to the hydrophobic substances, and either already during of B eladungsvons or form agglomerates and subsequently precipitating. As a result, the possible uses of the dispersions are considerably restricted. For example, an application of the dispersions in transparent layers, as are often used in reproduction technology, is ruled out because of the turbidity which the dispersions cause.
  • a photographic material which contains an anionic polyurethane in one or more of its gelatin layers, in which a water-insoluble optical brightener is contained.
  • the amount of the optical brightener which can be introduced into the gelatin layer with the aid of the polyurethane is limited to a maximum of 5% by weight.
  • polyurethanes are described in mixtures of high-boiling and low-boiling solvents for introducing photographic additives into photographic pouring solutions.
  • a disadvantage of the process is the additional loading of the photographic layers thus produced with the high-boiling solvents.
  • the ballast of high-boiling solvents hinders the formation of thin layers, as are required for recordings with high sharpness.
  • the precipitation dispersion process used here according to Angew. Macromol. Chem., 72 (1978), p. 115ff. requires considerable amounts of auxiliary solvents if it is to lead to reasonably fine-grain dispersions. This considerably limits the economic usability of the process.
  • the polyurethane latexes known from European patent application 0014 921 and loaded with hydrophobic compounds are produced by loading the finished polymer dispersion, the particle size of which is therefore already fixed.
  • a disadvantage of this procedure is that the particles are enlarged by the loading process. This gives dispersions which are coarser than the starting dispersions and which therefore tend to sediment and can cloud the photographic layers.
  • the object of the invention is to develop a method which enables the production of stable, fine-grained dispersions of hydrophobic substances in water with the least possible technical outlay.
  • the invention relates to a process for the preparation of dispersions of hydrophobic substances in water by loading an ionically modified polymer with the hydrophobic substance, which is characterized in that the hydrophobic substance together with an ionomeric polyaddition or condensation product in an organic, water-miscible Solvent with a boiling point less than 120 ° C or in a mixture, the organic solvent with water in a weight ratio of 50: 50 to 100: 0, preferably 75: 25 to 95: 5, the solution is mixed with water so that a solvent / Water mixture in a weight ratio of 10: 1 to 1:10 and then the organic solvent is removed.
  • the ionomeric polyaddition or polycondensation products used according to the invention contain 4 to 180 milliequivalents per 100 g of ionic groups or of groups which can be converted into ionic groups and / or 1 to 20% by weight of within a poly ether chain built-in alkylene oxide units of the formula -CH 2 -CH 2 -0-, where the polyether chain can be contained laterally or in the main chain.
  • ionomeric products which can be used according to the invention, hereinafter the term “ionomeric products” is to be used for this, include polyurethanes, polyesters, polyamides, polyureas, polycarbonates, polyacetals or polyethers.
  • ionomeric products which simultaneously belong to two or more types of polymer, such as, for example, polyester polyurethanes, polyether polyurethanes, polyester ureas, which contain 4 to 100 milliequivalents per 100 g of ionic groups or groups which can be converted into ionic groups and / or 1 to 20% by weight contain ethylene oxide units of the formula -CH 2 -CH 2 -O- built into a polyethylene chain, it being possible for the polyether chain to be contained laterally or in the main chain.
  • Ionomeric products as used in the present invention are known as such and e.g. in Angewandte macromolecular Chemistry, 26 (1972), pages 45 to 106; Angewandte Chemie 82 (1970), pages 53 ff; J. Oil. Col. Chem. Assoc. 53 (1970), page 363. Further descriptions of suitable ionomeric products can be found in DE-OSs 2 637 690, 2 642 973, 2 651 505, 2 651 506, 2 659 617, 2 729 245, 2 730514, 2 732 131, 2 734 576 and 2 811 148.
  • Ionomeric products with anionic groups are preferred. Ionomeric products which are particularly suitable for the process of the invention are described in DE-PS 1 472 746. These ionomeric products are based on polyurethanes, which consist of compounds with several reactive hydrogen atoms with one Molecular weight of 300 to 10,000, polyisocyanates and optionally chain extenders with reactive hydrogen atoms can be obtained.
  • isocyanate groups still present in them are reacted with a compound having at least one active hydrogen atom and at least one salt-like group or one capable of salt formation. If compounds with groups capable of salt formation are used, the resulting anionic polyurethanes are then at least partially converted into the salt form in a manner known per se.
  • salt-like group means the following groupings: 4 to 180 milliequivalents per 100 g of ionic groups or groups which can be converted into ionic groups are used.
  • the starting components for the preparation of the anionic polyurethanes are, for example, the compounds described below:
  • connections are essentially linear and have a molecular weight of about 300 to 10,000, preferably 500 to 4000.
  • the compounds known per se have terminal hydroxyl and amino groups.
  • Polyhydroxyl compounds such as polyesters, polyacetals, polyethers, polyamides and polyesteramides are preferred.
  • the hydroxyl number of these compounds therefore corresponds to approximately 370 to 10, in particular 225 to 28.
  • polyethers e.g. the polymerization products of ethylene oxide, propylene oxide, tetrahydrofuran, butylene oxide and their mixed or graft polymerization products, and also the condensates obtained by condensation of polyhydric alcohols or mixtures thereof and the products obtained by alkoxylation of polyhydric alcohols.
  • polyacetals e.g. the compounds that can be prepared from hexanediol and formaldehyde are questionable.
  • the predominantly linear condensates obtained from polyvalent saturated carboxylic acids and polyvalent saturated alcohols, amino alcohols, diamines and their mixtures are suitable as polyesters, polyester amides and polyamides.
  • Polyhydroxyl compounds already containing urethane or urea groups and also modified natural polyols such as castor oil or carbohydrates can also be used.
  • aromatic and aliphatic diisocyanates are suitable as polyisocyanates, e.g. 1,5-naphthylene diisocyanate, 4,4'-diphenylmethane diisocyanate, 4,4'-diphenyldimethylmethane diisocyanate, di- and tetraalkyldiphenylmethane diisocyanate, 4,4'-dibenzyl diisocyanate, 1,3-phenylene diisocyanate, 1,4-phenylene diisocyanate, the isomers of tolylene diisocyanate, if appropriate in a mixture, preferably the aliphatic diisocyanates, butane-1,4-diisocyanate, hexane-1,6-diisocyanate, dicyclohexylmethane diisocyanate, cyclohexane-1,4-diisocyanate and isophorone diisocyanate.
  • inorganic bases basic reacting or base releasing compounds such as monovalent metal hydroxides, carbonates and oxides such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate.
  • organic bases such as tert. Amines, e.g. Trimethylamine, triethylamine, dimethylamine ethanol, dimethylamine propanol, ammonia and the like.
  • the amount of the polyisocyanates is preferably selected so that all groups which are reactive with isocyanate groups react.
  • the reaction is optionally carried out with the use of solvents, low-boiling solvents with a boiling point below 120 ° C., such as, for example, acetone, ethanol, methanol, tert-butanol, methyl ethyl ketone, acetonitrile, tetrahydrofuran, dioxane, which are suitable, if appropriate may contain proportionate water.
  • solvents low-boiling solvents with a boiling point below 120 ° C.
  • solvents low-boiling solvents with a boiling point below 120 ° C.
  • solvents low-boiling solvents with a boiling point below 120 ° C.
  • water can optionally be used without the addition of organic solvents.
  • the predominantly linear, high molecular weight anionic polyurethanes are generally obtained as clear to slightly opalescent solutions in the polar solvents mentioned. Their solids content is about 5 to 50% by weight of ionic polyurethane.
  • NCO prepolymer is prepared from 75 g (0.356 mol) of a polyester of adipic acid and 1,4-butanediol (dewatered) and 95 g (0.546 mol) of 2,4-tolylene diisocyanate at 75 to 85 ° C in 1.5 hours (1 , 78% NCO). It is dissolved hot in 1060 g of tetrahydrofuran and a solution of 53 g (0.13 mol) of an aqueous solution of the sodium salt of N-sulfonatoethylethylenediamine in 100 ml of water is added at 50.degree. - After 5 minutes, another 500 g of tetrahydrofuran is added because of the sharp increase in viscosity.
  • a clear polyurethane-polyurea solution is obtained with the following characteristic data:
  • a solution adjusted to 30% solids by dilution with acetone has a viscosity of 3000 cp.
  • hydrophobic substances which can be processed in accordance with the invention include e.g. hydrophobic UV absorbers, filter dyes, color couplers, sensitizers, color developer compounds, silver halide developer compounds, compounds releasing or releasing hydrophobic dyes, optical brighteners, antioxidants, silver halide solvents, radiation-curable compounds, photoinitiators or mixtures of such substances.
  • Suitable water-miscible organic solvents for the process of the invention are those which are able to dissolve both the ionomeric products and the hydrophobic substances.
  • examples of such solvents are acetone, tetrahydrofuran, dioxane, isopropanol, methanol, ethanol, methyl ethyl ketone, acetonitrile.
  • the amounts of hydrophobic substances used for the process of the invention are generally 2 to 200% by weight of hydrophobic substance per 100% by weight of ionomeric product. Weight ratios of hydrophobic substance to ionomeric product of 1:20 to 1: 1 are preferred.
  • water is allowed to flow into a solution of the water-insoluble hydrophobic substance and the ionomeric product in a water-miscible low-boiling solvent or solvent / water mixture with stirring.
  • the solvent is separated from the resulting dispersion by distillation or by other suitable separation processes such as dialysis or ultrafiltration.
  • the method of the invention is excellently suitable for incorporating color couplers into color photographic recording materials.
  • the silver halide emulsions mixed with the color couplers can advantageously be cast into thin color photographic layers in which the color couplers can react with oxidized color developer compounds, for example consisting of primary aromatic amines, to form dyes.
  • oxidized color developer compounds for example consisting of primary aromatic amines
  • Examples of color couplers which can be incorporated into photographic recording layers by the process of the invention come from the group of R -dicarbonyl compounds, ⁇ -ketoacetonitriles, 5-pyrazolones, pyrazolobenzimidazoles, indazolones, phenols or naphthols.
  • hydrophobic color couplers are particularly suitable for incorporation into color photographic layers by the process of the invention.
  • the method of the invention enables the production of stable dispersions of hydrophobic substances in water without the simultaneous use of wetting agents and energy-intensive dispersing devices.
  • the dispersions show a surprisingly high sedimentation stability and are therefore ideally storable, a property that e.g. proves to be a valuable advantage in the production process of recording layers.
  • the lightfastness of the image dyes of color photographic recording layers which contain the dispersions prepared by the process according to the invention is significantly improved. Due to the lack of the wetting agent and high-boiling solvents in the dispersions of the invention, it is also possible to keep the binder content of color photographic recording layers low, because the dispersions can be used without the use of protective colloids, e.g. Gelatin, stable.
  • the process of the invention differs from known processes for the production of aqueous dispersions of hydrophobic substances, in particular in that it does not start from polymer dispersions, but rather from solutions of the ionomer products described above, from which the particles containing the hydrophobic substances are reconstructed.
  • the loaded particles obtained from such solutions are smaller than the particles formed by known processes by loading polymer dispersions.
  • the use of the dispersion produced by the process of the invention is accordingly associated with a number of advantages: the dispersions can be stored without the risk of sedimentation, they there is no clouding of the photographic layers and the embedded hydrophobic substances, because of the large surface area of the particles, are more accessible in the photographic layer structure.
  • the dispersion is prepared based on the method described in DD-PS 1 38 831 by stirring a solution of polyurethane and coupler in water and evaporating the solvent. It is a precipitation dispersion.
  • water is metered into a solution of polyurethane and coupler and the solvent is evaporated off. In this case, the dispersion is formed by reversing the phase (see Dispersion 1).
  • the precipitation dispersion process is therefore unsuitable for the production of finely divided dispersions.
  • the procedure was as described for dispersion 1. However, the color coupler M 2 was used. The dispersion obtained had a solids content of 23.2%.
  • Example 1 of DE-OS 2 541 274 a latex was produced and loaded with the color coupler Y 6 in the manner described.
  • the weight ratio of color coupler to polymer was 1: 1.
  • the particle sizes were 240 nm and 210 nm, respectively.
  • Dispersions 2, 3 and 4 of DD-PS 138 831 as dispersions A, B and C were reworked with the couplers described by their formulas.
  • the polymer (VI) was a polyaddition product composed of 218.5 g of adipic acid-hexanediol-neopentylglycol polyester (OH number 63), 55 g of 1,6-hexane diisocyanate and 27.8 g of sodium 1,2-diaminoethane-N-propanesulfonate used.
  • This mixture is stirred at 50 ° C in 100 ml of water with a low-speed laboratory stirrer, the low-boiling organic solvent is removed by vacuum distillation and stabilized by 100 ml of a 5% aqueous gelatin solution.
  • This mixture is stirred at 50 ° C in 100 ml of a 5% aqueous gelatin solution (phthaloyl gelatin).
  • a 5% aqueous gelatin solution phthaloyl gelatin.
  • the gelatin / polymer / coupler phase is flocculated by changing the pH and the low-boiling organic solvent is thus removed.
  • the dispersions produced in the manner described sedimented and the non-sedimented portions had a particle size of approximately 1 ⁇ m. Mixing the dispersions with gelatin produced cloudy layers.
  • Example A was repeated. Instead of coupler Y 5, coupler M 2 was used. The dispersion obtained had a particle size of 28 nm.
  • Example A was repeated. Instead of coupler Y 5, coupler C 1 was used. The dispersion obtained had a particle size of 34 nm.
  • Dispersions 1 to 15 were admixed with samples of a silver halide gelatin emulsion which had been sensitized to blue, green or red in accordance with the color coupler introduced.
  • the silver halide gelatin emulsion used consisted of 75 g of silver bromide (3 mol% iodide) and 72 g of gelatin based on 1 kg of emulsion.
  • the emulsions prepared in this way were applied to cellulose triacetate layer supports provided with an adhesive layer and dried.
  • the sensitivity of the color photographic layers which contain dispersions prepared in accordance with the invention is up to 4 DIN higher than that of the comparison layers.
  • the color couplers contained in the samples according to the invention - with only minor deviations - coupled with steeper gamma.
  • the color couplers prove to be particularly reactive.
  • the data relating to the absorption of the dyes are in no way affected by the use of the dispersions of the invention.
  • the dispersions ⁇ , 2b and 3 and the comparative dispersions 8, 9b and 10 were mixed in a silver halide gelatin emulsion of the composition described in Example 1.
  • the ready-to-pour emulsions thus obtained were then applied to cellulose triacetate substrates provided with adhesive layers.
  • Table 2 shows the outstanding fine-grain nature of samples 1, 2b, 3 according to the invention in comparison with the corresponding comparison samples 8, 9b and 10, respectively.
  • the quotient Q the absolute value of which is proportional to the influence of citracin acid, was also found to be significantly lower in the samples according to the invention. This is related to the already mentioned high reactivity of the color couplers dispersed in the manner according to the invention.
  • Dispersions 1, 2a, 6, 7 and 15 according to the invention, as well as comparative dispersions 8, 9a, 13 and 14, were mixed in with the silver halide gelatin emulsions sensitized accordingly to the couplers and the Pour emulsions onto a baritized paper base. The samples were then exposed as described in Example 1 and processed in the following baths.
  • UV protective film which contains a hydroxybenztriazole as the absorbing substance
  • a photographic emulsion layer consisting ilberbromidemulsion from a S, a dispersion according to the invention or atechnologiesemulgat, gelatin and a curing agent prepared and dried. After drying, the layer contained 20% by volume of AgBr and 30% by volume of the dispersion according to the invention or of the comparison emulsifier. 36 mm wide strips of this material were adjusted for 3 days in a climate of 20% RH at 23 ° C. The measurement was made using the drop hammer method in this climate. The test specimens are placed in loops with the emulsion layer on the outside and the energy that leads to the breakage of the film is determined. Around 100 breaking attempts were carried out, at least half of which are said to break.
  • the measured fracture energy values B of the layers which contain the dispersion according to the invention are compared with the fracture energy values obtained with the comparison emulsifiers.
  • the increase in the breaking strength of the layers with the dispersions according to the invention was calculated in% using the following formula.
  • Example A was repeated. Instead of coupler Y 5, coupler M 2 was used. The dispersion obtained had a particle size of 28 nm.
  • Example A was repeated. Instead of coupler Y 5, coupler C 1 was used. The dispersion obtained had a particle size of 34 nm.

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  • Chemical & Material Sciences (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Polyurethanes Or Polyureas (AREA)
  • Silver Salt Photography Or Processing Solution Therefor (AREA)
  • Processes Of Treating Macromolecular Substances (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
EP81107366A 1980-09-30 1981-09-17 Procédé de fabrication de dispersions d'agents de copulation hydrophobes dans l'eau ainsi que l'utilisation de ces dispersions dans la fabrication de matériaux de reproduction sensibles à la lumière Expired EP0049399B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19803036846 DE3036846A1 (de) 1980-09-30 1980-09-30 Verfahren zur herstellung von dispersionen hydrophober substanzen in wasser
DE3036846 1980-09-30

Publications (3)

Publication Number Publication Date
EP0049399A2 true EP0049399A2 (fr) 1982-04-14
EP0049399A3 EP0049399A3 (en) 1982-11-24
EP0049399B1 EP0049399B1 (fr) 1986-09-10

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EP81107366A Expired EP0049399B1 (fr) 1980-09-30 1981-09-17 Procédé de fabrication de dispersions d'agents de copulation hydrophobes dans l'eau ainsi que l'utilisation de ces dispersions dans la fabrication de matériaux de reproduction sensibles à la lumière

Country Status (5)

Country Link
US (1) US4388403A (fr)
EP (1) EP0049399B1 (fr)
JP (1) JPS5787429A (fr)
CA (1) CA1163891A (fr)
DE (2) DE3036846A1 (fr)

Cited By (7)

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EP0130115A2 (fr) * 1983-06-20 1985-01-02 EASTMAN KODAK COMPANY (a New Jersey corporation) Compositions de latex de polycarbonate
EP0185248A2 (fr) * 1984-12-15 1986-06-25 Agfa-Gevaert AG Produits de polyaddition ou polycondensation, la dispersion aqueuse dérivant de ceux-ci ainsi qu'un matériau d'enregistrement photographique contenant un composant photographique en forme de ces produits polymères
EP0205075A2 (fr) * 1985-06-11 1986-12-17 Agfa-Gevaert AG Matériau d'enregistrement photographique couleur et méthode pour préparer des images photographiques en couleurs
EP0282814A2 (fr) * 1987-03-14 1988-09-21 Agfa-Gevaert AG Matériau d'enregistrement photographique couleur pour le procédé de diffusion transfert
EP0361322A2 (fr) * 1988-09-26 1990-04-04 Eastman Kodak Company Procédé pour la précipitation des dispersions colloidales stables de composantes dégradables en base pour systèmes photographiques en absence de stabilisateurs polymères stériques
DE102007020523A1 (de) 2007-05-02 2008-11-06 Helling, Günter, Dr. Metallsalz-Nanogel enthaltende Polymere
EP2690127A1 (fr) * 2012-07-27 2014-01-29 nolax AG Procédé de fabrication d'une dispersion polymère et son utilisation

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US4401787A (en) * 1981-07-07 1983-08-30 Eastman Kodak Company Latex compositions for water resistant coating applications
EP0250658B1 (fr) * 1986-07-04 1989-09-06 Agfa-Gevaert N.V. Matériau récepteur d'images de colorant
US4851327A (en) 1986-07-17 1989-07-25 Fuji Photo Film Co., Ltd. Photographic color photosensitive material with two layer reflective support
IT1199806B (it) * 1986-12-18 1989-01-05 Minnesota Mining & Mfg Processo per la formazione di immagini fotografiche a colori stabili
DE3768246D1 (de) * 1987-01-16 1991-04-04 Agfa Gevaert Nv Bildempfangsmaterial zur verwendung in diffusionsuebertragungs-umkehrverfahren.
DE3778545D1 (de) * 1987-09-29 1992-05-27 Agfa Gevaert Nv Farbstoffbildempfangsmaterial.
JP2630410B2 (ja) * 1988-01-12 1997-07-16 富士写真フイルム株式会社 ハロゲン化銀カラー感光材料
GB8820547D0 (en) * 1988-08-31 1988-09-28 Vickers Plc Improvements in/relating to polymeric compounds
US4957857A (en) * 1988-12-23 1990-09-18 Eastman Kodak Company Stabilization of precipitated dispersions of hydrophobic couplers
US5015564A (en) * 1988-12-23 1991-05-14 Eastman Kodak Company Stabilizatin of precipitated dispersions of hydrophobic couplers, surfactants and polymers
JP2813746B2 (ja) * 1989-05-16 1998-10-22 富士写真フイルム株式会社 ハロゲン化銀写真感光材料
US5013640A (en) * 1989-06-15 1991-05-07 Eastman Kodak Company Preparation of low viscosity small-particle photographic dispersions in gelatin
DE69029828T2 (de) * 1989-09-05 1997-07-31 Eastman Kodak Co Photographische gelbe Kuppler, Verfahren zur ihrer Herstellung und Zwischenprodukte dafür
US5089380A (en) * 1989-10-02 1992-02-18 Eastman Kodak Company Methods of preparation of precipitated coupler dispersions with increased photographic activity
US5087554A (en) * 1990-06-27 1992-02-11 Eastman Kodak Company Stabilization of precipitated dispersions of hydrophobic couplers
US5256527A (en) * 1990-06-27 1993-10-26 Eastman Kodak Company Stabilization of precipitated dispersions of hydrophobic couplers
US5173398A (en) * 1990-10-31 1992-12-22 Konica Corporation Silver halide color photographic light-sensitive material
EP0490416B1 (fr) * 1990-11-30 1996-05-15 Agfa-Gevaert N.V. Matériau récepteur d'images comprenant du polycarbonate ou du polypropylène substraté
US5624467A (en) * 1991-12-20 1997-04-29 Eastman Kodak Company Microprecipitation process for dispersing photographic filter dyes
US5582960A (en) * 1995-02-17 1996-12-10 Eastman Kodak Company Photographic print material
US5594047A (en) * 1995-02-17 1997-01-14 Eastman Kodak Company Method for forming photographic dispersions comprising loaded latex polymers
US5770352A (en) * 1996-04-18 1998-06-23 Eastman Kodak Company High activity photographic dispersions with ultra low levels of permanent solvent
US5830632A (en) * 1996-10-31 1998-11-03 Eastman Kodak Company Photographic element containing dispersions of high dye-yield couplers having improved photographic activity
CN105093804A (zh) * 2014-12-16 2015-11-25 铜陵翔宇商贸有限公司 胶片用停显液及其制备方法
DE102015008388A1 (de) 2015-06-29 2016-12-29 WAE Marketing GbR (vertr. Gesellsch. Herr Oliver Westerbeek, 51069 Köln) Verwendung einer polymeren Zubereitung zur Beschichtung von Handschuhen

Citations (5)

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DE1597467A1 (de) * 1967-07-22 1970-04-09 Agfa Gevaert Ag Optische Aufheller enthaltendes photographisches Material
DE2651506A1 (de) * 1976-11-11 1978-05-24 Bayer Ag Verfahren zur herstellung von in wasser dispergierbaren polyurethanen
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US4199363A (en) * 1974-09-17 1980-04-22 Eastman Kodak Company Processes for achieving uniform, efficient distribution of hydrophobic materials through hydrophilic colloid layers and loaded latex compositions

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JPS5931688B2 (ja) * 1977-05-10 1984-08-03 富士写真フイルム株式会社 写真用添加剤の分散方法
JPS5599947A (en) * 1979-01-24 1980-07-30 Toray Ind Inc Aqueous disperison of polyester, and its preparation
JPS5599950A (en) * 1979-01-24 1980-07-30 Toray Ind Inc Aqueous dispersion of polyester
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US4247627A (en) * 1979-10-10 1981-01-27 Eastman Kodak Company Photographic elements having hydrophilic colloid layers containing hydrophobic ultraviolet absorbers uniformly loaded in latex polymer particles

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CH461265A (de) * 1965-03-17 1968-08-15 Agfa Gevaert Ag Photographisches Material mit mindestens einer gelatinehaltigen Schicht
DE1597467A1 (de) * 1967-07-22 1970-04-09 Agfa Gevaert Ag Optische Aufheller enthaltendes photographisches Material
US4199363A (en) * 1974-09-17 1980-04-22 Eastman Kodak Company Processes for achieving uniform, efficient distribution of hydrophobic materials through hydrophilic colloid layers and loaded latex compositions
DE2651506A1 (de) * 1976-11-11 1978-05-24 Bayer Ag Verfahren zur herstellung von in wasser dispergierbaren polyurethanen
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Cited By (12)

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EP0130115A2 (fr) * 1983-06-20 1985-01-02 EASTMAN KODAK COMPANY (a New Jersey corporation) Compositions de latex de polycarbonate
EP0130115A3 (en) * 1983-06-20 1987-01-07 Eastman Kodak Company Polycarbonate latex compositions
EP0185248A2 (fr) * 1984-12-15 1986-06-25 Agfa-Gevaert AG Produits de polyaddition ou polycondensation, la dispersion aqueuse dérivant de ceux-ci ainsi qu'un matériau d'enregistrement photographique contenant un composant photographique en forme de ces produits polymères
EP0185248A3 (en) * 1984-12-15 1988-02-03 Agfa-Gevaert Ag Polyaddition or polycondensation products, their aqueous dispersions as well as a photographic recording material containing a photographic compound in the form of such polymeric products
EP0205075A2 (fr) * 1985-06-11 1986-12-17 Agfa-Gevaert AG Matériau d'enregistrement photographique couleur et méthode pour préparer des images photographiques en couleurs
EP0205075A3 (en) * 1985-06-11 1988-12-21 Agfa-Gevaert Ag Colour-photographic recording material and method for making colour-photographic images
EP0282814A2 (fr) * 1987-03-14 1988-09-21 Agfa-Gevaert AG Matériau d'enregistrement photographique couleur pour le procédé de diffusion transfert
EP0282814A3 (en) * 1987-03-14 1989-09-06 Agfa-Gevaert Ag Colour photographic recording material for the diffusion transfer process
EP0361322A2 (fr) * 1988-09-26 1990-04-04 Eastman Kodak Company Procédé pour la précipitation des dispersions colloidales stables de composantes dégradables en base pour systèmes photographiques en absence de stabilisateurs polymères stériques
EP0361322A3 (fr) * 1988-09-26 1992-02-26 Eastman Kodak Company Procédé pour la précipitation des dispersions colloidales stables de composantes dégradables en base pour systèmes photographiques en absence de stabilisateurs polymères stériques
DE102007020523A1 (de) 2007-05-02 2008-11-06 Helling, Günter, Dr. Metallsalz-Nanogel enthaltende Polymere
EP2690127A1 (fr) * 2012-07-27 2014-01-29 nolax AG Procédé de fabrication d'une dispersion polymère et son utilisation

Also Published As

Publication number Publication date
JPS5787429A (en) 1982-05-31
EP0049399B1 (fr) 1986-09-10
JPH0315730B2 (fr) 1991-03-01
US4388403A (en) 1983-06-14
CA1163891A (fr) 1984-03-20
DE3175302D1 (en) 1986-10-16
EP0049399A3 (en) 1982-11-24
DE3036846A1 (de) 1982-05-27

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