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
  • G03C1/04—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein with macromolecular additives; with layer-forming substances
  • G03C1/053—Polymers obtained by reactions involving only carbon-to-carbon unsaturated bonds, e.g. vinyl polymers
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
  • C08F8/00—Chemical modification by after-treatment
  • C08F8/12—Hydrolysis
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
  • C08F8/00—Chemical modification by after-treatment
  • C08F8/44—Preparation of metal salts or ammonium salts
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
  • C08F2810/00—Chemical modification of a polymer
  • C08F2810/50—Chemical modification of a polymer wherein the polymer is a copolymer and the modification is taking place only on one or more of the monomers present in minority

Definitions

• ABSTRACT A light-sensitive photographic silver halide material containing hompolymers or copolymers of 1,3- dihydroxy-2-methylene-propane or derivatives thereof which have an advantageous stabilising effect on the photographic properties of the silver halide emulsion layers.
• This invention relates to a photographic material which contains at least one silverhalide emulsion layer, the stability of which has been improved by the addition of homopolymers or copolymers of 1,3-dihydroxy- 2-methylenepropane or derivatives thereof.
• light-sensitive silver halide emulsions particularly those which have been chemically sensitised, have a tendency to fog, i.e. to form nuclei which are capable of developing without having been exposed to light.
• Fogging occurs inparticular if the emulsions are stored too long, especially if they are stored at elevated temperatures and atmospheric moisture levels or if they are developed for too long or at excessively high temperatures. It may also be caused by certain additives, by excessive ripening of the emulsions, etc.
• the tendency of photographic silver halide emulsions to fog can to a certain extent be suppressed by the addition of so-called stabilisers or anti-fogging agents.
• Substances which have this effect are, for example, heterocyclic mercapto compounds or inorganic or organic mercury compounds.
• a light-sensitive photographic material containing at least one silver halide emulsion layer which contains homopolymers or copolymers of 1,3-dihydroxy-2-methylenepropane and/or l,3-dicarbamoxy-2-methylenepropane or derivatives thereof.
• R represents hydrogen, a straight or branched chain alkyl group preferably containing 1 to 4 carbon atoms, a substituted or unsubstituted aryl group such as phenyl or tolyl, a cyanoalkyl group such as cyanomethyl, cycanoethyl or cyanopropyl, or the group --CONHR
• R represents hydrogen, a straight or branched chain alkyl group preferably containing from 1 to 6 carbon atoms, a cycloalkyl group such as cyclopentyl or cyclohexyl, a substituted or unsubstituted aryl group such as phenyl or tolyl or an alkoxy alkyl group such as methoxy methyl;
• Z represents acrylic, methacrylic, fumaric or maleic acid or their ammonium or alkali metal salts; acrylamide ormethacrylamide; an N-alkyl (preferably C acrylamide or methacrylamide; an N-hydroxyalkyl acrylamide or methacrylamide such as N-hydroxymethyl acrylamide or methacrylamide an N-oxoalkyl acrylamide or methacrylamide such as diacetone acrylamide; fumaric or maleic acid semiamide or their ammonium or alkali metal salts; a monohydroxyalkyl acrylate or methacrylate such as 2-hydroxyethyl methacrylate; a dihydroxyalkyl acrylate or methacrylate such as 2,2-dihydroxymethyl propyl methacrylate; a dialkylaminoalkyl acrylate or methacrylate such as 2-dimethylaminoethyl methacrylate; a sulfoalkyl carboxylate such as 2-sulfoethyl meth
• Y represents a polymerisab le group selected from styrene, acrylic acid ,esters such as methyl or ethyl acrylic acid estersand the compound in which R represents an alkyl group, for example a methyl group;
• polymerisation is carried out as a radical polymerisation by means of peroxides (e.g. benzoyl peroxide, di-tert.butyl peroxide, dilauryl peroxide, dicumyl peroxide, tert.butyl hydroperoxide, cumene hydroperoxide or diacetyl peroxide), percarboxylic acid esters (e.g. tert.butyl peracetate, perbenzoate, peroctoate, perpinalate or perisobutyrate), percarbonates (e. g. isopropyl peroxydicarbonate or ethylhexyl percarbonate), acyl sulphonyl peroxides (e.g.
• peroxides e.g. benzoyl peroxide, di-tert.butyl peroxide, dilauryl peroxide, dicumyl peroxide, tert.butyl hydroperoxide, cumene hydroper
• acetyl cyclohexane sulphonyl peroxide or azo compounds. It is carried out in emulsion or in the absence of a solvent and the molecular weights of the polymers determined by osmometric methods of measurement may be from 500 to 3,000. These starting materials are soluble in most organic solvents such as acetone, ether, alcohol, benzene, dioxane, dimethylformamide, dimethylsulphoxide, ethyl acetate, or petroleum ether.
• the polymeric acetate is saponified by acid or alkaline saponification.
• a preferred saponification method for example, poly-l,3-diacetoxy-Z-methylenepropane is dissolved in alcohol and converted into the desired poly-1,3-dihydroxy-2-methylenepropane by the addition of a alcoholic sodium or potassium hydroxide solution at a temperature of between and C.
• a alcoholic sodium or potassium hydroxide solution at a temperature of between and C.
• Zemplens alcoholysis method which is known from the chemistry of sugars may be employed, using catalytic quantities of an alkali metal alcoholate. In both cases, the polyalcohol remains in solution and the solution is therefore evaporated to dryness.
• the methanolic or aqueous solution of poly-1,3-dihydroxy- Z-methylenepropane may be treated with ion exchangers.
• the residue obtained after removal of the alcohol used for saponification is then taken up again in a solvent such as dimethylformamide which will not dissolve alkali metal acetates, so that the product can then again be isolated by suction filtration of the salt and evaporation of the solution.
• an alcoholic alkali metal hydroxide is 4 added to the poly-l,3-diacetoxy-Z-methylenepropane dissolved in alcohol/ester to precipitate the poly-1,3- dihydroxy-Z-methylenepropane which is immediately ready for use after removal of the solvent and drying.
• Polyethers of formula I can be obtained by reacting the polymeric alcohol with alkylating agents such as diazomethane, dialkyl sulphate or p-toluene sulphonic acid esters or by the addition of acrylonitrile. According to another method of preparing such ethers, the reaction is preceded by the polymerisation of 1,3- dichloro-2-methylenepropane which can be obtained by reacting l,3-dihydroxy-Z-methylenepropane with thionyl chloride or phosgene. The polymer is then reacted with alcoholates.
• alkylating agents such as diazomethane, dialkyl sulphate or p-toluene sulphonic acid esters or by the addition of acrylonitrile.
• the reaction is preceded by the polymerisation of 1,3- dichloro-2-methylenepropane which can be obtained by reacting l,3-dihydroxy-Z-methylenepropane with thionyl
• polymers of formula II in which R is not CONHR copolymers are first prepared from mixtures of 5 99.5 mols-% of l,3-diacetoxy-2-methylenepropane and 0.5 mols-% of monomers which contain hydrophilic groups such as acrylic or methacrylic acid, itaconic acid, fumaric acid, maleic acid anhydride, acrylamides or methacrylamides, itaconic, fumaric or maleic acid amides or their N-substituted derivatives such as N-alkyl-, N-hydroxyalkylor N-oxoalkylamides, for example N-methyl-(meth) acrylamide, N- acid semiamide, N-hydroxymethyl(meth) acrylamide or diacetone acrylamide; or also N-vinyl pyrrolidone or N-vinyl caprolactam.
• hydrophilic groups such as acrylic or methacrylic acid, itaconic acid, fumaric acid, maleic acid anhydride,
• the copolymers are subsequently saponified with an alcoholic alkali metal alcoholate by Zernplens method or with alcoholic alkali metal hydroxide.
• an alcoholic alkali metal alcoholate by Zernplens method or with alcoholic alkali metal hydroxide.
• a sulpho group may subsequently be introduced by reaction with alkane sultones.
• l,3-diacetoxy-Z-methylene propane and acrylonitrile are copolymerised in a molar ratio of 0.3 l7 99.7 83 in an aqueous suspension with the aid of a redox system such as potassium persulphate/sodium metabisulphite as described in German Pat. Specification No. 2,047,249 and the product is then hydrolysed, a high-molecular weight, water-soluble copolymer is obtained which also contains carboxyl or carboxylate and primary hydroxyl groups as well as containing additional amide groups, depending on the conditions under which the reactions are carried out.
• a redox system such as potassium persulphate/sodium metabisulphite
• polymers are comparable in their molecular weights with terpolymers of formula III which are obtained by the alkaline saponification of copolymers, e.g. from styrene, l,3-diacetoxy-Z-methylenepropane and maleic acid anhydride.
• terpolymers of formula III which are obtained by the alkaline saponification of copolymers, e.g. from styrene, l,3-diacetoxy-Z-methylenepropane and maleic acid anhydride.
• These starting materials are preferably used in a molar ratio of styrene 1,3- diacetoxy-2-methylenepropane maleic acid anhydride l:l:2 because the best yields and molecular weights are then obtained.
• the carboxylate functions formed by saponification render the products water-soluble but the water insoluble acids may be prepared from them, and these may then be converted into amides while the remaining acid may be neutralised with an alkali in order to obtain again the required solubility in water.
• the terpolymers of formula III have relative viscosities of up to 4.0 and hence the highest molecular weights, followed by the copolymers of formula II 1.3; in the case of the acrylonitrile copolymers mentioned above also 4) while the uni-l,3-diacetoxy-2-methylenepropanes (approximately 1.08) are low-molecular weight compounds a fact which is also confirmed by osmometric determinations.
• the derived homopolymers of formula I are found to have degrees of polymerisation of from 3 to 20.
• 1,3- dihydroxy-2-methylenepropane can be obtained by the hydrolysis of 1,3 -diacetoxy-Z-methylenepropane which can in turn be obtained from isobutene, acetic acid and oxygen by methods which have already been described.
• the addition of the isocyanates is carried out in the absence of solvents or in inert solvents such as benzene, ethyl acetate, chloroform, methylene chloride, or carbon tetrachloride, at room temperature or at boiling point.
• the dicarbamates separate in the cold and can immediately be isolated in an analytically pure form by suction filtration.
• l,3-dicarbamoxy-2-methylenepropane as well as 1,3-di-N,N-methylcarbamoxy-2-methylenepropane or l,3-di-N,N-ethyl-carbamoxy-2-methylenepropane are polymerised, preferably solvent-free, with peroxides (benzoyl peroxide, di-tertbutyl peroxide, dilauroyl peroxide, dicumyl peroxide, tert.butyl hydroperoxide, cumene hydroperoxide or diacetyl peroxide); percarboxylic acid esters (tert.-butyl peracetate, perbenzoate, peroctoate, perpivalate or perisobutyrate); percarbonates (isopropyl peroxydicarbonate or ethylhexyl percarbonate); acyl sulphonyl peroxides (ace
• the method selected for copolymerising the dicarbamates to polymers of formula 11 is either that of solventfree polymerisation or polymerisation in solvents which may be water, alcohols, ketones, esters, aromatic solvents, N-monoalkylated or dialkylated cyclic lactams, carboxylic acid amides such as N-methyl pyrrolidone, dimethylformamide, dimethyl sulphoxide, glycol carbonate, butyrolactone, etc..
• solvents which may be water, alcohols, ketones, esters, aromatic solvents, N-monoalkylated or dialkylated cyclic lactams, carboxylic acid amides such as N-methyl pyrrolidone, dimethylformamide, dimethyl sulphoxide, glycol carbonate, butyrolactone, etc.
• solvents which may be water, alcohols, ketones, esters, aromatic solvents, N-monoalkylated or dialkylated cyclic lactams, carboxy
• the following may be used as comonomers for 1,3-dicarbamoxy-2-methylenepropane or 1,3- di-N,N-alkylcarbamoxy-2-methylenepropane: Acrylic and methacrylic acid, acrylamide and methacrylamide, N-hydroxyalkyl acrylamide or methacrylamide, e.g.
• dialkylaminoalkyl acrylates or methacrylates such as 2-dimethylaminoethyl methacrylate, vinyl pyridines, vinyl imidazoles, and sulphoalkyl acrylates or methacrylates, e.g. 2-sulphoethyl methacrylate.
• the preparation of the copolymers of dicarbamates and maleic acid semiesters or amides may also be carried out by subsequently reacting the copolymers of dicarbamates and maleic acid anhydride with alcohols or amines. Furthermore, the free acidic or amino functions of the copolymers may be converted into the salt form.
• the quantities used are 05-90 mols-% of comonomer and 99.5 mols-% of dicarbamate.
• the relative viscosities of the copolymers obtained (1 part by weight/ 100 parts by volume of solvent) are from 1.05 to 3.0.
• polymerised monomer is then evaporated off at 12 mm. 0.39 mol are obtained at this stage. No more volatile constituents are then isolated under a high vacuum at 120 130C.
• the polymer which remains behind is a clear, pale, highly viscous thermoplastic mass which is soluble in all organic solvents such as acetone, ether, alcohols, benzene, dioxane, dimethylformamide, dimethylsulphoxide, ethyl acetate, or petroleum ether.
• 0.0343 mol of di-tert.butyl peroxide is added to 2.48 mol of the dicarbamate which is then heated to C for 20 hours under an atmosphere of nitrogen with stirring. After the addition of a further portion of 0.0343 mol of the peroxide, stirring is continued at the same temperature for another 8 hours. When cold, the mass is crushed and stirred with ethyl acetate for 1 hour at room temperature. The supernatant ester is then decanted off and the residue dried. Yield: 1.78 mol 360 parts by weight (72 a (1 part by weight/ 100 parts by volume of dimethylforrnamide): 1.05; Molecular weight (methanol): 670.
• the polymer is soluble in cold water but partly separates as an oil when heated and redissolves on cooling.
• the yield is 975 parts by weight (97.5 a (1 part by weight/100 parts by volume of dimethylformamide): 1.23.
• Elementary analysis shows that the copolymer contains 76.7 mols-% of N-vinyl pyrrolidone. Its melting range is 170 200C.
• An infra-red spectrum shows the ester band at 1,750 cm and the cyclic amide function at 1,670 cm.
• the copolymer is then dissolved in 2,200 parts by volume of anhydrous methanol with stirring and 60 parts by volume of a 10 sodium methylate solution are intro Jerusalem.
• the reaction mixture is left to stand at room temperature for 12 hours and then evaporated to dryness under vacuum. A syrup remained from which the remaining quantities of methanol are removed by drying at elevated temperature.
• diacetoxy-2-methylenepropane are heated to C and 0.00343 mol of di-tert.-bu'tyl peroxide are added. After a reaction time of 2 hours, another 0.00343 mol of the peroxide are added and this is repeated after 4 hours.
• the total polymerisation time is 8 hours at 130 C.
• the viscous mass is taken up in benzene and precipitated with petroleum ether. By working up and drying the product in this way, 125 parts by weight (83.5 are isolated. It has a relative viscosity of a 1.08 (1 part by weight/100 parts by volume of dimethylformamide) and contains 41.8 mol-% of N-vinyl pyrrolidone. Alcoholysis is carried out as already described.
• styrene 0.5 mol of styrene, 0.5 mol of 1,3-diacetoxy-2- methylenepropane and 1 mol of maleic acid anhydride are dissolved in 900 parts by volume of benzene by heating and stirring. Polymerisation is initiated at boiling point by the addition of 0.0115 mol of tert.butyl peroctoate. The reaction mixture is boiled under reflux for 7 hours and the precipitated polymer is then suction-filtered, washed and dried.
• polyvi nyl alcohol is incompatible with gelatine when added in quantities of more than 5
• the basic unit CHEOH cn on is very similar to the basic vinyl alcohol unit and from a formal point of view constitutes a dimer of the vinyl alcohol, the two polymers differ in their properties. It was not foreseeable that they would also differ from each other in photographic respects.
• Polyvinyl alcohol is inert in photographic emulsions.
• the polymers to be used according to the invention have the advantage over many of the known stabilisers that they have an excellent stabilising effect on the photographic properties such as sensitivity, gradation and clarity and if anything improve the graininess of the emulsions. 1f the compounds are added to the emulsion before chemical after-ripening, greater sensitivity can be obtained for the same amount of fogging.
• the polymers to be used according to the invention may be added to the usual photographic layers, that is to say tolayers used in general for photographic materials such as light-sensitive silver halide emulsion layers, protective layers, filter layers, antihalation layers, back coatings, baryta layers or, in general, any photographic auxiliary layers.
• the light-sensitive emulsion layers to which the polymers may be added may be, for example, layers which are based on emulsions which have not been sensitised or on orthochromatic, panchromatic or infraredemul- 'sions, X-ray emulsions or other s'pectrally sensitised emulsions.
• the layersused for various black-and-white and colour photographic processes are also suitable.
• the polymers have been found to be particularly advantag eous for use in photographic layer combinations used for carrying out colour photographic processes, for example those which containemulsion layers with colour couplers or emulsion layers which are to be treated with solutions which contain colour couplers.
• These compounds may be added to the light-sensitive silver halide emulsions at any stage of the preparation of the emulsions but they are preferably added as casting additive before the stage of after-ripening.
• the quantity added may vary within wide limits but quantities of 50 g per mol of silver halide have generally been found to be sufficient. Particularly good results are obtained if the emulsions contain from 20 30 g of the compounds according to the invention per mol of silver halide.
• the compounds according to the invention are advantageously added in the form of solutions.
• Water is a suitable solvent for this purpose.
• the usual silver halide emulsions are suitable for this invention.
• the silver halide contained in these emulsions may be silver chloride, silver bromide or mixtures thereof, which may have a small silver iodide content of up to mols
• the binder used for the photographic layers is preferably gelatine although this may be partly or completely replaced by other natural or synthetic binder.
• suitable natural binders Alginic acid and its derivatives such as salts, esters or amides; cellulose derivatives such as carboxymethyl cellulose; hydroalkyl celluloses such as hydroxyethyl cellulose; starch or derivatives thereof such as ethers or esters or carrageenates.
• Suitable synthetic binders are, for example, polyvinyl alcohol, partly saponified polyvinyl acetate, and polyvinyl pyrrolidone.
• the emulsions may also be chemically sensitised, e.g. by adding sulphur compounds such as allyl isothiocyanate, allyl thiourea, and sodium thiosulfate at the chemical ripening stage.
• Reducing agents may also be used as chemical sensitisers, e.g. the tin compounds described in Belgian Pat. Specifications Nos. 493,464 and 568,687 or polyamines such as diethylenetriamine or aminomethyl sulphinic acid derivatives, e.g. according to Belgian Pat. Specification No. 547,323.
• Noble metals such as gold, platinum, palladium, iridium, ruthenium or rhodium and compounds of these metals are also suitable chemical sensitisers. This method of chemical sensitisation has been described in the article by R. Koslowsky, Z. Wiss. Phot. 46, 65 72 (1951).
• the emulsions may also be sensitised with polyalkylene oxide derivatives, e.g. with a polyethylene oxide which has a molecular weight of between 1000 and 20,000, or with condensation products of alkylene oxides and aliphatic alcohols, glycols, cyclic dehydration products of hexitols, with alkyl-substituted phenols, aliphatic carboxylic acids, aliphatic amines, aliphatic diamines and amides.
• the condensation products should have a molecular weight of at least 700 and preferably more than 1000.
• the emulsions may also be optically sensitised, e.g. with the usual polymethine dyes such as neutrocyanines, basic or acid carbocyanines, rhodacyanines, hemicyanines, styryl dyes, and oxonoles.
• Sensitisers of this kind have been described in the work by vF.M. Hamer The'Cyanine Dyes and related Compounds (1964).
• the emulsions may contain other known stabilisers, e.g. homopolar or salt-type compounds of mercury which contain aromatic or heterocyclic rings such as mercaptotriazoles, simple mercury salts, sulphonium mercury double salts and other mercury compounds.
• suitable stabilisers include azaindenes, particularly tetraor pentaaza'indenes and especially those which are substituted with hydroxyl or amino groups. Compounds of this kind. have been described in the article by Birr, Z. Wiss. Phot. 47, 2 58 (1952).
• Other suitable stabilisers are, among others, heterocyclic mercapto compounds, e.g. phenyl mercaptotetrazole, quaternary benzothiazole derivatives, and benzotriazole.
• the emulsions may be hardened in the usual manner, for example with formaldehyde or halogenated aldehydes which contain a carboxyl group such as mucobromic acid, diketones, methane sulphonic acid esters, and dialdehydes.
• formaldehyde or halogenated aldehydes which contain a carboxyl group such as mucobromic acid, diketones, methane sulphonic acid esters, and dialdehydes.
• the emulsions may also contain colour couplers in the form of solutions or dispersions.
• EXAMPLE 1 A maximum sensitivity silver iodobromide gelatine emulsion containing 6 mols-% of silver iodide was prepared in the usual manner by running the silver nitrate solution at intervals into a solution which contained gelatine in addition to potassium bromide and iodide. The emulsion was flocculated in known manner with ammonium sulfate and freed from the soluble salts. The flocculate was redispersed in warm water, ripening gelatin which contains sulfur was added and the dispersion was ripened to optimum sensitivity in the presence of gold(I) thiocyanate complexes and sodium thiosulfate. The finished emulsion contained 54 g of silver per kg in the form of silver halide.
• a highly sensitive silver iodobromide gelatine emulsion containing 5 mols-% of silver iodide was prepared as described in Example 1. 30
• the pH of the layer is about 6.5-7.
• Hardening bath 0.3 g of sodium hydroxide 0.5 g of sodium hexametaphosphate 9.04 g of soda 20 ml of 37 formalin water up to l l.
• a cyan dye was formed in the exposed areas and the orange red masking dye was preserved in the unexposed areas. Sensitometric determination shows that excellent masking of the material is obtained in the blue and green ranges of measurement.
• the sensitivity of sample B is l.5 higher than that of A.
• a light-sensitive photographic material containing at least one silver halide emulsion layer, said emulsion layer containing at least one compound of the formulae:
• R represents H, alkyl, aryl, cyanoalkyl or -CO- NHR
• R represents H, alkyl, cyc'loalkyl, aryl or alkoxy alkyl
• Z represents acrylic, methacrylic, fumaric or maleic acid groups, optionally in a salt form, an N-alkyl-, N-hydroxyalkylor N-oxoalkyl acrylamide or methacrylamide group, furmaric or maleic acid semiamide optionally in a salt form, monoor dihydroxyalkyl acrylate or methacrylate, sulphoalkyl acrylate or methacrylate, or vinyl-pyrrolidone, -caprolactam, -piperidine or -imidazole,
• Y polymerisable group selected from styrene
• Light-sensitive photographic material according to claim 1 characterised in that it contains poly-1,3- diacetoxy-2-methylenepropane.
• Light-sensitive photographic material according to claim 1 characterised in that it contains poly-1 ,3-diN,- N'-methyl-carbamoxy-2-methylenepropane.
• Light-sensitive photographic material characterised in that it contains a copolymer of the formula wherein 35 mols-% and m 65 mols-%.
• Light-sensitive photographic material characterised in that it contains a polymer of the formula OONu CO-NH wherein n 5 80 mols-%, m 10 50 mols-% and p 10 45 mols-%.

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• 1973
  • 1973-06-27 DE DE2332562A patent/DE2332562A1/de active Pending
• 1974
  • 1974-06-19 BE BE1006031A patent/BE816540A/nl unknown
  • 1974-06-20 US US481187A patent/US3926635A/en not_active Expired - Lifetime
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  • 1974-06-26 CA CA203,456A patent/CA1021982A/en not_active Expired
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  • 1974-06-27 FR FR7422495A patent/FR2235390B1/fr not_active Expired

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