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
• • 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
  • G03C1/067—Additives for high contrast images, other than hydrazine compounds

Definitions

• This invention relates to a novel light-sensitive silver halide photographic material used for formation of photographic images. More particularly, it relates to a novel light-sensitive silver halide photographic material which is capable of forming dot images of high contrast and has high usefulness in the filed of lithography.
• This kind of light-sensitive silver halide photographic emulsion is known as a lith type light-sensitive silver halide photographic material, which is generally used during the lithographic procedures to convert the variation in concentrations of continuous gradation in an original to the aggregation of dots having larger to smaller areas in proportion to the concentrations.
• the lith type light-sensitive silver halide photographic material is used, whereby dot images are formed by photographing an original through means of a cross line screen or a contact screen, and then carrying out development with use of a so-called lith developer, or a lith type developing solution, which has very low sulfite ion concentration and, in addition, contains only a hydroquinone developing agent.
• Such developing solution has inferior preservativity and is subject to autoxidation. Accordingly, in order for lithographers to obtain halftone negative and halftone positive immages always having high quality, it is required to control the developing solution to keep constant its degree of activity which may have decreased with lapse of time, thereby inevitably being accompanied with troublesome operations.
• Japanese Unexamined Patent Publication No. 106244/1981 discloses that the high contrast images can be obtained by using a hydrazine compound and incorporating into a developing solution an amino compound in an amount by which the development may be promoted.
• Japanese Patent Publications No. 17825/1984, No. 17818/1984, No. 17819/1984, No. 17820/1984, No. 17821/1984, No. 17826/1984, No. 17822/1984, etc. disclose light-sensitive silver halide photographic materials containing a tetrazolium compound.
• the tetrazolium compound disclosed in the latter arts which, however, has no drawback as in the former art, can not be said to be very satisfactory in the light of high contrastiness and dot quality.
• a light-sensitive silver halide photographic material having on a substrate at least one silver halide emulsion layer and at least one hydrophilic colloid layer, wherein a triphenyltetrazolium compound represented by the following General Formula (I) is incorporated in at least one of said silver halide emulsion layer and said hydrophilic colloid layer, whereupon this invention has been accomplished.
• a triphenyltetrazolium compound represented by the following General Formula (I) is incorporated in at least one of said silver halide emulsion layer and said hydrophilic colloid layer, whereupon this invention has been accomplished.
• R 1 , R 2 and R 3 each represent a hydrogen atom or a group showing a negative value in Hamett's sigma value ( ⁇ p ), and X ⁇ represents an anion; except that R 1 , R 2 and R3 are hydrogen atoms at the same time.
• a light-sensitive silver halide photographic material which is stable as being free from detorioration of its performance even during storage under high temperature and high humidity, can be obtained by providing a light-sensitive silver halide photographic material having on a substrate at least one silver halide emulsion layer and at least one hydrophilic colloid layer, wherein the silver halide grains contained in said silver halide emulsion layer are those formed in the presence of a water soluble rhodium salt used in an amount of 1 x 10 -7 to 5 x 10- 7 mole per mole of silver halide and, at the same time, at least one triphenyltetrazolium compound represented by the following General Formula (I)' is incorporated in said at least one hydrophilic colloid layer.
• the subsitutents R 1 , R 2 and R 3 in the phenyl groups of the triphenyltetrazolium compound represented by General Formula (I) or (I)' represent a hydrogen atom or a group showing a negative value in Hamett's sigma value (ap) which indicates an electron withdrawing degree, namely, an electron withdrawing group.
• Hamett's sigma value in the phenyl substitution is seen from a number of papers, for instance, a report by C. Hansch et al, disclosed in Journal of Medical Chemistry, vol. 20, page 304, 1977.
• R l , R 2 and R 3 is a hydrogen atom
• at least one of the remaining two substituents represents an alkyl group.
• both the two substituents are alkl groups, it is preferred that both of them are alkyl groups having the same carbon atoms, and it is further preferred that they are the same alkyl group.
• the tetrazolium compound used in this invention can be readily synthesized by a method dislcosed, for instance, in Chemical Reviews, Vol. 55, pp.335-483.
• the tetrazolium compound of this invention may preferably be used in an amount ranging from about 1 mg to about 10 g, preferably from about 10 mg to about 2 g, and more preferably from about 10 mg to about 1 g, per mole of the silver halide contained in the light-sensitive silver halide photographic material of this invention.
• the light-sensitive silver halide photographic material comprises a substrate and at least one silver halide emulsion layer and at least one hydrophilic colloid layer provided by coating on the substrate.
• This silver halide emulsion layer may be either directly coated on the substrate or coated thereon by interposing a hydrophilic colloid layer containing no silver halide emulsion, and the hydrophilic colloid layer may be either coated on the silver halide emulsion layer or coated as a protective layer between the substrate and the silver halide emulsion layer.
• the silver halide emulsion layers when provided in plurality, may comprise silver halide emulsion layers each having different sensitivity, e.g., high sensitivity and low sensitivity.
• the tetrazolium compound of this invention in the silver halide emulsion layer and/or the hydrophilic colloid layer, there may be employed a method in which the tetrazolium compound is added by dissolving it in a suitable aqueous and organic solvent; a method in which the compound is added by dissolving it in a suitable aqueous and organic solvent and then mixing in a matrix of a hydrophilic colloids such as gelatin or gelatin derivatives, or after dispersing it in a latex. Any of these method may be employed in this invention.
• the tetrazolium compound used in this invention can attain preferable image properties when used singularly. Also, this tetrazolium compound does not adversely affect the image properties even when two or more kinds of the compound are used in combination at an appropreate proportion. Further, the tetrazolium compound of this invention and the other tetrazolium compounds outside this invention may also be used in combination at an appropreate proportion.
• the tetrazolium compound according to this invention may be incorporated into a silver halide emulsion layer.
• it is incorporated into a hydrophilic colloid layer directly adjacent to a hydrophilic colloid layer containing a silver halide emulsion, or into an adjacent hydrophilic colloid layer by interposing an intermediate layer.
• anion may include, for example, acid radicals of inorganic acids such as perchloric acids, acid radicals of organic acids such as sulfonic acids and carboxylic acids, and anion type activators.
• lower alkylbenzenesulfonate anions such as p-toluensulfonate anion, p-dodecylbenzenesulfonate anions, alkylnaphtha- lenesulfonate anions, laurylsulfate anions, tetraphenyl- borates, dialkylsulfosuccinate anions such as di-2-ethylhexylsulfosuccinate anion, polyether alcohol sulfuric acid ester anions such as cetylpolyethenoxysulfate anion, stearate anion, polyacrylate anion, etc.
• lower alkylbenzenesulfonate anions such as p-toluensulfonate anion, p-dodecylbenzenesulfonate anions, alkylnaphtha- lenesulfonate anions, laurylsulfate anions, t
• These anions may be previously mixed with the tetrazolium compound of this invention and thereafter added to a hydrophilic colloid layer. Alternatively, they may be added singularly to a silver halide emulsion layer or a hydrophilic colloid layer containing or not containing the tetrazolium compound of this invention.
• the amount of adding the water soluble rhodium salt may be 1.0 x 10- 7 to 5.0 x 10- 7 mole per one mole of silver halide.
• the water soluble rhodium salt is in less than 1.0 x 10- 7 mole, the stability under high temperature and high humidity which is an aim in this invention will become insufficient.
• the desensitizing effect by the watersoluble rhodium salt to the silver halide will increase as well known to a person skilled in the art, thereby making it difficult to obtain desired sensitivity.
• the silver halide used in the light-sensitive silver halide photographic material of this invention is preferably silver chlorobromide having the AgCl/AgBr ratio of 100/0 to 2/98, particularly preferably the one having the AgCl/AgBr ratio of 90/10 to 50/50.
• the silver halide grains are preferably of monodispersed type, having a mean grain size of from 0.15 ⁇ m to 0.40 ⁇ m and a grain size distribution coefficient, represented by (standard deviation in grain size distribution)/(mean grain size), of 15 % or less.
• the silver halide emulsion layer according to this invention may be prepared in the following manner.
• the silver halide emulsion in the silver halide emulsion layer may be prepared by a method of preparing a silver halide photographic emulsion by adding in an aqueous solution of hydrophilic colloid an aqueous solution of a water soluble silver salt and an aqueous solution of a water soluble halide in accordance with a double jet method, wherein said aqueous solution of a water soluble silver salt and said aqueous solution of a water soluble halide are added at an addition rate such that the rate of growth of silver halide grains in said aqueous solution of hydrophilic colloid does not exceed the critical growth rate, and EAg value of said aqueous solution of hydrophilic colloid is kept at substantially constant value set within the range of from 140 mV to 200 mV during a period corresponding to one-thirtieth (1/30) to one-f
• the rate of growth of silver halide grains does not exceed the critical growth rate means that the supersaturated concentration at which new nuclei of silver halide grains are generated is not ocurred in a solution.
• the critical growth rate herein mentioned can be determined by actually forming crystals in an actual system while varying the rate of addition of various silver ions and halogen ions, and making sampling from a reaction vessel to confirm the presence or absence of the generation of new nuclei by an electron microscopic observation.
• the EAg value is a concept well known to a person skilled in the art, designating a silver potential which is indicated by a value measured with use of a metal silver electrode and a double junction type saturated Ag/Cl reference electrode.
• EAg value is disclosed in Japanese Unexamined Patent Publication No. 197534/1982.
• the silver halide used in this invention may be sensitized by use of various kinds of chemical sensitizers.
• the sensitizers may include, for example, active gelatins, sulfur sensitizers (such as sodium thiosulfate, arylthiocarbamide, thiourea and arylisothiacyanate), selenium sensitizers (such as N,N-dimethylselenourea and selenourea), reduction sensitizers (such as triethylenetetramine and stannic chloride) and various noble metal sensitizers typically exemplified by potassium chloroorite, potassium orithiocyanate, potassium chloroorate, 2-orosulfobenzothiazol methylchloride, ammonium chloropalladate, potassium chloroplatinate, sodium chloropalladite, etc. Each of them may be used singularly or in combination of two or more kinds. When gold sensitizers are used, ammonium thiocyanate may be used as an auxiliary.
• the silver halide emulsion used in this invention may be subjected to optical sensitization with use of one or more of sensitizing dyes to impart sensitivity to each of the desired light-sensitive wavelength region.
• the sensitizing dyes to be used may include various ones, and the optical sensitizing dyes advantageously usable in this invention may inlclude cyanines, merocyanines, trinulear or tetranuclear merocyanines, trinuclear or tetranuclear cyanines, styryls, holopolar cyanines, hemicyanines, oxonols, hemioxonols, etc.
• optical sensitizing dyes are preferably those which contain in a part of the structure a basic radical such as thiazoline and thiazole or a nucleus such as rhodanine, thiohydanto- in, oxazolidinedione, berbituric acid, thioberbituric acid and pyrazolone, as a nitrogen-containing heterocyclic nucleus.
• a basic radical such as thiazoline and thiazole
• nucleus such as rhodanine, thiohydanto- in, oxazolidinedione, berbituric acid, thioberbituric acid and pyrazolone
• Such nucleus may undergo alkyl, hydroxyalkyl, halogen, phenyl, cyano or alkoxy substitution.
• these optical sensitizing dyes may have undergone condensation with a carbocyclic ring or a heterocyclic ring.
• the silver halide emulsion used in this invention may be stabilized by use of the compounds disclosed, for instance, in U.S. Patents No. 2,444,607, No. 2,716,062 and No. 3,512,982, West German Patent Publications No. 1,189,380, No. 2,058,626 and No. 2,118,411, Japanese Patent Publication No. 4133/1968, U.S. Patent No. 3,342,569, Japanese Patent Publication No. 4417/1972 No. 4417/1972, West German Patent Publication No. 2,149,789, Japanese Patent Publications No. 2825/1964 and No.
• hydrophilic colloid particularly advantageously usable in this invention is gelatin.
• Hydrophilic colloids other than gelatin may include, for example, colloidal albumin, agar, gum arabic, alginic acid, hydrolyzed cellulose acetate, acrylamide, imidized polyamide, polyvinyl alcohol, hydrolyzed polyvinyl acetate, gelatin derivatives such as phenylcarbamyl gelatin, acylated gelatin and phthalated gelatin as disclosed in U. S . Patents No. 2,614,928 and No.
• graft polymers obtained by attaching to gelatin a copolymerizable monomer having an ethylene group, such as styrene acrylate, acrylate, methacrylic acid and methacrylate, as disclosed in U.S. Patents No. 2,548,520 and No. 2,831,767.
• hydrophilic colloids may be applied to a layer containing no silver halide, for example, an antihalation layer, a protective layer, an intermediate layer, etc.
• the substrate, or support material, used in this invention typically includes, for example, a baryta paper, a polyethylene-coated paper, a polypropylene synthetic paper, a glass plate, cellulose acetate, cellulose nitrate, a polyester film such as polyethyleneterephthalate, a polyamide film, a polypropylene film, a polycarbonate film, a polystyrene film, etc.
• These substrates are each selected optionally depending on the intended use of the light-sensitive silver halide photographic material.
• the light-sensitive material according to this invention has, on the support material as mentioned above, at least one layer selected from the group of silver halide emulsion layer and hydrophilic colloid layer, wherein the tetrazolium compound of this invention is incorporated in said at least one layer.
• the hydrophilic colloid layer is coated as a protective layer on the silver halide emulsion layer to have a desired film thickness, preferably of from 0.1 to 10 ⁇ m, particularly preferably from 0.8 to 2 ⁇ m.
• various kind of photographic additives for example, a gelatin plasticizer, a hardening agent, a surface active agent, an image stabilizing agent, a ultraviolet absorbent, an antistain agent, a pH adjuster, an antioxidant, an antistatic agent, a thickner, a graininess improver, a dyestuff, a moldant, a whitening agent, a development rate regulator, a matt agent, etc., so far as the effect of the invention is not impaired.
• a gelatin plasticizer for example, a hardening agent, a surface active agent, an image stabilizing agent, a ultraviolet absorbent, an antistain agent, a pH adjuster, an antioxidant, an antistatic agent, a thickner, a graininess improver, a dyestuff, a moldant, a whitening agent, a development rate regulator, a matt agent, etc.
• those which are particularly preferably usable in this invention are, as the thickner or the plasticizer, the substances disclosed, for instance, in U.S. Patent No. 2,960,404, Japanese Patent Publication No. 4939/1968, West German Patent Publication No. 1,904,604, Japanese Unexamined Patent Publication No. 63715/1973, Japanese Patent Publication No. 15462/1970, Belgium Patent No. 762,833, U.S. Patent No. 3,767,410 and Belgium Patent No.
• the hardening agent may include an aldehyde type, an epoxy type, an ethyleneimine type, an active halogen type, a vinylsulfone type, an isocyanate type, a sulfonate type, a carbodiimide type, a mucochloric acid type and an acyloyl type hardening agents;
• the ultraviolet absorbent may include the compounds disclosed, for instance, in U.S. Patent No. 3,253,921 and British Patent No.
• 1,309,349 in particular, 2-(2'-hydroxy-5-tertiary butyl phenyl)benzotriazole, 2-(2-hydroxy-3,5-di-tertiary butyl phenyl)- benzotriazole, 2-(2-hydroxy-3-tertiary butyl-5-butyl phenyl)-5-chlorobenzotriazole, 2-(2-hydroxy-3,5-di- tertiary butyl phenyl)-5-chlorobenzotriazole, etc;
• the dyestuff may include the compounds disclosed, for instance, in U.S. Patent No. 2,072,908, West German Patent No. 107,990, U.S. Patent No. 3,048,487 and U.S.
• the light-sensitive silver halide photographic material containing the tetrazolium compound of this invention in the silver halide emulsion layer and/or the hydrophilic colloid layer can be developed in the presence of a compound represented by General Formula (II) below.
• R 1 represents a nitro group at the 5- or 6 -position
• R 2 represents a hydrogen atom or a lower alkyl group having 1 to 5 carbon atoms
• M represents a hydrogen atom, an alkali metal atom, an alkaline earth metal atom or a cation such as ammonium ion.
• the compound represented by General Formula (II) may include, for example, 5-nitroindazole, 6-nitroindazole, etc., to which, however, this invention is by no means limited.
• the compound represented by General Formula (II) may be added to a developing solution by dissolving it in an organic solvent such as diethylene glycol, triethylene glycol, ethanol, diethanolamine and triethanolamine, an alkali such as sodium hydroxide, an acid such as acetic acid, or may be added directly without such a procedure.
• organic solvent such as diethylene glycol, triethylene glycol, ethanol, diethanolamine and triethanolamine, an alkali such as sodium hydroxide, an acid such as acetic acid, or may be added directly without such a procedure.
• the compound represented by General Formula (II) may be contained in the concentration within the range of from about 1 mg to 1000 mg, preferably from about 50 mg to 300 mg, per one liter of the developing solution.
• This developing agent may be used in combination with the above-mentioned compound represented by General Formula (II).
• sulfite such as potassium sulfite and ammonium sulfite may be used as a preservative. Even if it is used, the effect of this invention will not be damaged, and this can be said to be one of the features of this invention. Hydroxylamines and hydrazide compounds may also be used as the preservative.
• alkali hydroxide alkali carbonate or amine which is usually used in a black and white developing solution
• an inorganic development restrainer such as potassium bromide and an organice development restrainer such as benzotriazole
• agent of capturing metal ions such as ethylenetetradiamine (IV) acetic acid, a development accelarator such as methanol, ethanol, benzylalcohol, polyalkyleneoxide, a surface active agent such as sodium alkylarylsulfonate, natural saponin, saccarides and an alkyl ester of the above compound, a hardening agent such as glutaraldehyde, formalin and glyoxal, and an ion strength regulator such as sodium sulfate.
• an inorganic development restrainer such as potassium bromide and an organice development restrainer such as benzotriazole
• agent of capturing metal ions such as ethylenetetradiamine (IV) acetic acid
• the developing solution used in this invention may further contain alkanol amines and glycols as organic solvents.
• the alkanol amines include, for example, monoethanol amine, diethanol amine and triethanol amine, and preferably used is triethanol amine. These alkanol amines may be used in an amount of 5 to 500 g, preferably 20 to 200 g, per one liter of the developing solution.
• the above glycols include ethylene glycol, diethylene glycol, propylene glycol, triethylene glycol, 1,4-butandiol, 1,5-pentandiol, etc., and preferably used is diethylen glycol.
• the glycols may be used in an amount of 5 to 500 g, preferably 20 to 200 g, per one liter of the developing solution.
• These organic solvents may be used singularly or in combination.
• the light-sensitive silver halide photographic material according to this invention can achieve sensitivity characteristics very excellent in the storage stability by processing with use of the developing agent containing such a development restrainer as mentioned above.
• the developing agent to be composed according to the above-mentioned has the pH value of 9 to 12, but a preferable pH value is 10 to 11 in the light of the preservability and the photographic characteristics.
• the light-sensitive silver halide photographic material according to this invention may be processed under various conditions.
• the processing temperature for instance, is preferably 50 0 C or lower, particularly preferably, 30°C or lower.
• the development may be completed in 3 minutes in general, particularly preferably in 2 minutes to often bring about desired results.
• optionally employable processing steps other than the development are, for example, water wahing, stopping, stabilizing, fixing, and further optionally, prehardening, neutralization, etc., which may be omitted accordingly.
• these processing steps may be carried out in either the so-called development by hand such as dish development and frame development or the mechanical development such as roller development and hanger auto development.
• Silver chlorobromide emulsions were prepared by use of the following solutions, Solution A, Solution B and Solution C.
• Solution B and Solution C were added by a double jet method using a mixing stirrer disclosed in Japanese Unexamined Patent Publications No. 92523/1982 and No. 92524/1982.
• EAg value was changed from 160 mV to the EAg value of 120 mV after 5 minutes from the beginning of the addition by using 3 ml/lit. of an aqueous solution of sodium chloride. Thereafter this value was maintained until the mixing was completed.
• the EAg was controlled by using 3 moles/lit. aqueous solution of sodium chloride.
• used were a silver metal electrode and a double junksion type saturated Ag/AgCl reference electrode (To constitute the electrode was used a double juncsion disclosed in Japanese Unexamined Patent Publication No. 197534/1982.).
• the system was controlled by use of a 3 % aqueous solution of nitrous acid to keep constant the pH value therein at 3.0.
• the emulsion was subjected to gold sulfur sensitization, and as a stabilizer 6-methyl-4-hydroxy-1,3,3a,7-tetrazaindene was added thereto. Further added as a sensitizing dye was 1-(8-hydroxyethyl)-3-phenyl-5-[(3-y-sulfopropyl-a-benzoxazolidine)-ethylidene]thio- hydantoin in an amount of 150 mg per one mole of Ag (hereinafter ".../Ag 1 mole").
• the thus optically sensitized emulsion were divided into 20 fractions, to each of which was added a substituted triphenyltetrazolium chloride as shown in Table 2 at the addition rate of 700 mg/Ag 1 mole, to which further added were sodium triisopropylnaphthalenesulfonate in 600 mg/Ag 1 mole, saponin in 3.5 g/Ag 1 mole and a styrene/maleic acid copolymer in 2 g/Ag 1 mole, and then the emulsions were each applied on a polyethyleneterephthalate film by coating to have the thickness of Ag 4.0 g/m 2 .
• a gelatin layer (gelatin 1.2 g/m 2 ) containing diethylsuccinate sulfonic acid (10 mg/m 2 ) as a spreading agent and formalin (25 mg/m2) as a hardening agent was overlapped by coating, and then dried to obtain samples (Samples 1 to 20).
• Sample Nos. 1 to 10 are samples according to this invention, each containing a tetrazolium salt having the substituent of which the ⁇ p value is negative. In Sample No. 11, there is no substituent.
• composition of developing solution :
• the above were dissolved in 500 ml of pure water in the order of Composition A and Composition B to make up one liter.
• the dot quality was evaluated by a five stage indication system in which a dot being small in fringe was indicated as 5 when the state of fringe (or fading) observed at the periphery of dots was visually judged as to the so-called 50 % dots which are equal in the dot portion area and the clear portion area. Namely, “5" means to be excellent and “1" means to be very poor. When the 50 % dot quality is not more than "3", such value can not in general be made acceptable.
• the light-sensitive silver halide photographic material according to this invention containing the tetrazolium compound having the electron donative substituent can achieve very high contrast and high dot quality, and has properties particularly excellent for the lithography.
• Solution B and Solution C After completion of the addition of Solution B and Solution C, the emulsion was subjected to Ostwald ripening, followed by desalting and water washing by a conventional method. Thereafter, 600 ml of an aqueous solution of ossein gelatin (containing 30 g of ossein gelatin) were added for dispersion with stirring at 55°C for 30 minutes to prepare 750 cc of the emulsion.
• EAg value used were a silver metal electrode and a double junction type saturated Ag/AgCl reference electrode (To constitute the electrode was used a double junction disclosed in Japanese Unexamined Patent Publication No. 197534/1982.).
• a gelatin layer containing 30 mg/m 2 of sodium 1-decyl-2-(3-isopentyl)succinate-2-sulfonate as a spreading agent and 25 mg/m 2 of formalin as a hardening agent was overlapped by coating so as to have the gelatin amount of 1.2 g/m 2 ).
• the sensitivity was calculated from the amount of exposure required for forming 95 % dot concentration, and indicated by a relative sensitivity when the sensitivity of Sample No. 1 is regarded as 100.

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• 1985
  • 1985-10-28 EP EP85307784A patent/EP0181728A3/en not_active Withdrawn
  • 1985-11-12 KR KR1019850008435A patent/KR860004333A/ko not_active Application Discontinuation
  • 1985-11-13 CN CN198585108256A patent/CN85108256A/zh active Pending

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