US3893861A - Silver halide photosensitive material - Google Patents

Silver halide photosensitive material Download PDF

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Publication number
US3893861A
US3893861A US400237A US40023773A US3893861A US 3893861 A US3893861 A US 3893861A US 400237 A US400237 A US 400237A US 40023773 A US40023773 A US 40023773A US 3893861 A US3893861 A US 3893861A
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United States
Prior art keywords
photosensitive material
silver halide
halide photosensitive
layer
polymer
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Expired - Lifetime
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US400237A
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English (en)
Inventor
Motoo Kogure
Yasuji Muroi
Kiyoyuki Miura
Motoo Watanabe
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Konica Minolta Inc
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Konica Minolta Inc
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    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
    • G03C1/00—Photosensitive materials
    • G03C1/76—Photosensitive materials characterised by the base or auxiliary layers
    • G03C1/7614—Cover layers; Backing layers; Base or auxiliary layers characterised by means for lubricating, for rendering anti-abrasive or for preventing adhesion
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
    • Y10S430/151—Matting or other surface reflectivity altering material

Definitions

  • This invention relates to a silver halide photosensitive material, More particularly, the invention relates to a silver halide photosensitive material having a specific kind of an outermost layer.
  • silver halide photosensitive materials are kept in the wound or lapped state in storage or use.
  • the front surface of one photosensitive material has a contact with the back surface of another photosensitive material.
  • the surface of photosensitive material has a contact with other material such as an interposition paper or a sensitizing paper for Roentgen photography, and there is frequently observed a phenomenon that a part or all of a structural layer of the photosensitive material such as a front surface layer or back surface layer of the photosensitive material is peeled by adhesion or sticking. This phenomenon is called sticking. This sticking phenomenon tends to occur frequently under high temperature and high hu midity conditions, and it results in serious damages to photosensitive materials.
  • a silver halide photosensitive material having an outermost layer comprising a polymer containing units of a monomer having a guanidylimino or guanidinoamino group in the side chain or an outermost layer comprising said polymer as a main constituent. This invention is based on the finding that this photosensitive material has a very high sticking-preventive effect.
  • R is a hydrogen atom or a lower alkyl group
  • CH fa CONHCH CH N -CCOCH2NH- R is a hydrogen atom or a lower alkyl group
  • R is a hydrogen atom, or a lower alkyl group, a phenyl group or a substituted phenyl group
  • R is a hydrogen or halogen atom or a lower alkyl group
  • X is an anion
  • M indicates a copolymerizable monomer
  • m and n indicate the mole percentages of the copolymerizable monomer components, respectively, the sum of m and n being I00 m being within a range of from about 20 to 100 and n being within a range
  • acrylates such as methyl methacylate, iethyl acrylate, ethyl acrylate, diacetone acrylate, dicetone methacrylate, 2-chloroethylacrylate, 2- hloroethyl methacrylate, chloromethyl acrylate, chlo omethyl methacrylate, glycidyl acrylate and glycidyl rethacrylate; acrylamides such as acrylamide, N- ihenylacrylamide, N-alkylacrylamides, diacetoneside chain and methods for the synthesis of these polymers are disclosed in Journal of Organic Chemistry, 23, 1117 (1958). Journal of Polymer Science, 32, 83 (1958) and French Pat. No. 2,079,149. US. Pat. No. 2.882,l56 and German Pat. No. 2,113,381.
  • n is about 30, n, is about 35, and m is about 35.
  • vinyl acetate type monomers in which the sum of :1 and n corresponds to n, m is such as vinyl acetate and vinyl chloroacetate; vinyl ethers such as methylvinylether; unsaturated acids such 2 CH f about 60, n is about 20, and :1. is about 20.
  • nitriles such as acrylonitrile and in which m is about 50 and n is about 50.
  • n corresponds to n
  • m is preferred that a layer of the polymer is formed by apabout 35, u is about 60, and n is about 5.
  • the polypolymer is generally applied in the form of an aqueous mer is used as the front surface layer or back surface l ti or a organi ol ent lution, preferably in layer of the silver halide photosensitive material or as th f f an organic Solvent l i A i l i both the front surface layer and the back surface layer.
  • organic solvent there can be In case the polymer is applied to the so called front surmentioned methanol, ethanol, propanol, acetone, etc.
  • the polymer may be applied to either or both such as ethylene glycol, ethylene glycol monomethyl ier. dioxane, etc.
  • the outer most layer composed of the above- :ntioned polymer or comprising it as a main constitut is formed on a silver halide photosensitive material. 2 stickingpreventive effect attained is especially ominent in the case of a photosensitive material of 2 type which has an anti-halation layer.
  • This anti-halation layer is colored so as to prevent so lled halation, and it generally contains as a coloring mponent carbon black or an alkali-soluble dye and a binder constituent a water-soluble or alkali-soluble sin. Because of characteristics required of this layer at the layer should be decolored or removed at the velopment step this layer should be selected so that has a good compatibility with a layer formed on the 1c of the photosensitive layer.
  • this anti-halation yer generally contains as main ingredients a dye or lgment and a water-soluble or alkali-soluble highlolecular substance.
  • water-soluble or alkalilluble substance there can be mentioned, for in ance, condensates of formaldehyde with aromatic irboxylic acids disclosed in U.S. Pat. No. 2,089,764, erman Pat. No. 584,622 and British Pat. Specification 0. 1,142,688, such as phenoxyacetic acidlrmaldehyde resins and salicylic acid-formaldehyde :sins; polyvinyl alcohol-acid anhydride reaction prod- :ts disclosed in U.S. Pat. No. 2,131,747, U.S. Pat. No. 271,234, U.S. Pat. No. 2,319,080 and U.S. Pat. No.
  • 1631/71, 2783/71 and 593/72 such as copolymers of at least one vinyl monomer selected from vinyl chloride, vinyl butyl ether, vinyl ethyl ether, styrene, acrylonitrile, nitrostyrene, vinyl acetate and ethylene and maleic anhydride, copolymers of said vinyl monomer and a semiester of fumaric acid or maleic acid with an alkyl alcohol; a lactone resin of said vinyl monomer and a glycolic acid, copolymers of at least one vinyl monomer selected from vinyl acetate, alkyl acrylates, alkyl methacrylates and styrene with a copolymerizable unsaturated acid such as acrylic acid, rnethacrylic acid and crotonic acid, and copolymers of vinyl acetate with an aryloxyacetic acid; polyvinyl substituted acetals having a carboxylic acid or sulfonic acid in the side chain, such as
  • the light-shielding substance of the antihalation layer there can be used, for instance, pigments such as carbon black, Prussian Blue, titanium white, zinc oxide and organic lake pigments, and various dyes disclosed in U.S. Pat, No. 2,150,695, U.S. Pat. No. 2,278,457, U.S. Pat. No. 2,282,890, U.S. Pat. No. 2,462,527, U.S. Pat. No. 2,984,568, U.S. Pat. No. 3,018,177, U.S. Pat. No. 3,364,029, British Pat. Specification No. 790,023, Japanese Pat. Publication No. 1716/64, Japanese Pat. Publication No. 8835/70, French Pat. No.
  • the anti halation layer comprising as the main constituents such watersoluble or alkali-soluble highmolecular substance as mentioned above and such dye or pigment as mentioned above is prepared, for instance, by a customary method comprising coating a coating liquid, which is prepared in the manner described below, directly or indirectly on the entire surface of a support on which a suitable undercoating has been formed in advance according to need, and drying the coated surface.
  • a coating liquid which is prepared in the manner described below, directly or indirectly on the entire surface of a support on which a suitable undercoating has been formed in advance according to need, and drying the coated surface.
  • carbon black is used as the light-shielding substance
  • the coating liquid is prepared, for instance, by a method such as disclosed in US. Pat. No.
  • 2,327,828 namely a method comprising mixing an alkali-soluble high-molecular substance and carbon black with a solvent for said highmolecular substance, dispersing the solids sufficiently in the liquid and diluting a viscous dispersion of carbon black with a suitable solvent.
  • a dye is used as the light shielding substance. a highmolecular substance is dissolved and diluted and a suitable amount of the dye is added to the resulting dilution to form a coating liquid.
  • alcohols such as methanol, ethanol, propanol, butanol, amyl alcohol, diacetone alcohol, ethylene glycol, ethylene glycol monomethyl ether, ethylene glycol monoethyl cther, ethylene glycol monoacetate, ethylene glycol monopropionate, ethylene glycol monobutyrate, diethylene glycol, diethylene glycol monomethyl ether and diethylene glycol monoethyl ether; ethers such as dioxane ethylene glycol dimethyl ether, ethylene glycol diethyl ether and anisole; ketones such as acetone, ethylmethylketone, isobutylmethylketone and cyclohexanone; esters such as methyl acetate, ethyl acetate, butyl acetate and methyl propionate; halogenated hydrocarbons such
  • a certain additive such as a surface active agent is added to an anti-halation layerforming coating liquid.
  • a surface active agent there can be mentioned those disclosed in US. Pat. No. 2.271.234, US. Pat. No. 2,333,809, U.S. Pat. No. 2,278,457, U.S. Pat. No. 2,80l,l9l, US. Pat. No. 2,976,160, British Pat. No. 536,680, Japanese Pat. Publication No. l3499/68, Japanese Pat. Publication No. 14503/67 and Japanese Pat. Publication No. 33466/70.
  • higher fatty acid esters of glycerin higher fatty acid esters of sorbito
  • higher fatty acid esters of polyoxyethylene sorbitol fatty acid esters of polyoxyethylene
  • aliphatic alcohol ethers of polyoxyethylene alkyl phenyl ethers of polyoxyethylene
  • alkyl sulfuric acid ester salts polyoxyethylene alkyl alkyl ether sulfuric acid ester salts
  • alkyl sulfosuccinic acid salts alkyl sulfosuccinic acid salts
  • N-acylsarcosine salts alkyl (polyoxyethylene) phosphoric acid esters, fatty acid esters, etc.
  • This invention has been detailed as regards a silver halide photosensitive material of the type including an anti-halation layer, but in this invention the silver halide photosensitive material to be used is not limited to this type and this invention can be applied to any other silver halide photosensitive material.
  • a silver halide photosensitive material having silver halide photosensitive layers on both the surfaces of a support or a silver halide photosensitive ma terial being free of an anti-halation layer but having a silver halide photosensitive layer on the one surface of a support
  • sticking occurs when the photosensitive material is kept in the lapperd state especially under high temperature and high humidity conditions.
  • this invention is applied to such silver halide photosensitive materials, occurrence of sticking can be completely prevented with no bad influences to photographic characteristics.
  • the polymer containing units of a monomer having a guanidylimino or guanidylamino group in the side chain is applied in an amount of about 0.001 to about I g per m of the photosensitive material.
  • a layer of such polymer is formed as an outermost layer of a photosensitive material by employing a solution of the polymer in aqueous liquid or an organic solvent such as mentioned above by means of coating or the like at a suitable stage of the photosensitive material manufacturing process.
  • the sticking-preventive effect of the polymer is not greatiy influenced by the average molecular weight thereof, but it is preferred that the polymer has an average molecular weight of about 5,000 to about 100,000.
  • An aqueous solution or organic solvent solution of the polymer may include various additives in addition to the polymer.
  • amphoteric, non-ionic or cationic polymers miscible with said polymer such as gelatin, non-ionic, cationic or amphoteric surface active agents, amphoteric, non-ionic or cationic antistatic agents, matting agents such as starch, colloidal silica, powdery silica and polymer beads, and lubricants can be optionally used according to need.
  • a silver halide photosensitive material to be used in this invention is formed by applying at least one layer of a silver halide photosensitive emulsion to one or both surfaces of a suitable support such as paper, resin laminated paper, glass, acetyl cellulose film, polyester film, polyamide film, polystyrene film and the like.
  • a suitable support such as paper, resin laminated paper, glass, acetyl cellulose film, polyester film, polyamide film, polystyrene film and the like.
  • Emulsions prepared by dispersing a suitable silver halide such as silver chloride, silver bromide, silver iodide, silver chlorobromide, silver iodobromide, silver chloroiodobromide and the like into a hydrophilic protective colloid are generally used as the silver halide emulsion.
  • hydrophilic protective colloid there can be used various substances such, for example, as gelatin, colloidal albumin, casein, cellulose derivatives, polyvinyl alcohol and polyacrylamides disclosed in US. Pat. No. 2,541,74l.
  • This emulsion can be chemically sensitized with use of a chemical sensitizer such, for example, as activated gelatin; sulfur compounds; noble metals (such as gold, rhodium, palladium iridium and platinurn), typical instances of which are ammonium chloropalladate, potassium chloroplatinate and sodium chloropalladite, and most preferably gold salts such as potassium chloroaurate, potassium auric thiocyanate, potassium chloroaurate, auric trichloride and 2- aurosulfobenzothiazole metochloride; and reducingg agents.
  • a chemical sensitizer such, for example, as activated gelatin; sulfur compounds; noble metals (such as gold, rhodium, palladium iridium and
  • this emulsion can be optically sensitized with optical sensitizer such as cyanine dyes, merocyanine dyes and the like, and it can be stabilized with such stabilizers as triazoles, azaindenes, quaternary benzothiazolium compounds and cadmium com pounds.
  • This emulsion may further comprise a sensitizer of the quaternary ammonium salt type or polyethylene glycol type, and in some case, it may comprise a plasticizer such as glycerin, hydroxyalkanes, ethylene bis-glycol esters, bis-succinates and acid amides, of the acrylic acid series.
  • this emulsion may comprise various photographic additives such as film-hardening agents, e.g., formaldehyde, chromalum, glyoxal and mucobromic acid; surfactants. e.g., saponin, lauryl and oleyl ethers of polyethylene glycol and sulfated polyethylene glycol ethers; anti-foggants; color coupler such as pyrazolone type magenta couplers, phenol type cyane couplers, yellow couplers and so called masking couplers (these couplers may be of either the protected type or Fisher dispersion type); and dispersing agents for color coupler, e.g., protecting solvents.
  • film-hardening agents e.g., formaldehyde, chromalum, glyoxal and mucobromic acid
  • surfactants e.g., saponin, lauryl and oleyl ethers of polyethylene glycol and sulfated
  • a protective layer is generally formed on this silver halide emulsion layer, and when two or more silver halide emulsion layers are formed, an intermediate layer or filter layer can be formed between the silver halide emulsion layers. Further, this silver halide emulsion layer may be composed of a layer of a high sensitivity and a layer of a low sensitivity.
  • any of silver halide photosensitive materials for the high resolution photography can be used in this invention.
  • the microcopy and for the ordinary photography can be used in this invention.
  • the above-mentioned polymer is applied as a front surface layer or back surface layer to one or both surfaces of such silver halide photosensitive material according to this invention, occurrence of sticking is prevented, and when such photosensitive material is allowed to stand under high temperature and high humidity conditions, there is no fear of occurrence of sticking.
  • the defects involved in silvler halide photosensitive materials formed by conventional sticking-preventing methods can be overcome.
  • EXAMPLE 1 An anti-halation layer comprising a carbon black dispersed lauryl alcohol-modified maleic anhydride vinyl acetate copolymer was formed on one surface of an undercoated polyethylene terephthalate film.
  • the resulting photosensitive material was cut into a width of H3 mm and 30 m of the photosensitive mate rial was wound on one reel.
  • the wound photosensitive material was allowed to stand at a temperature of 50C. and a relative humidity of 80% for 5 hours, transfer of the antihalation layer to the photosensitive layer by the sticking phenomenon was not observed at all. After the development treatment it was confirmed that the photographic characteristics were not adversely affected by provision of the above polymer layer.
  • a photosensitive material was prepared in the same manner as above except that an outermost layer of the compound l was not formed, and it was tested in the same manner as above. It was found that sticking occurred at several parts.
  • EXAMPLE 2 An anti-halation layer comprising a carbon black dispersed hydroxypropyl cellulose phthalate and methyl cellulose phthalate was formed on one surface of an acetyl cellulose film, and 21 methanol aqueous solution (lzl) containing 0.5% of the exemplified compound (5) (average molecular weight about 20,000; m about 50; n about 50) and a small amount of polyethylene glycol lauryl ether was coated on the antihalation layer in an amount of 20 cc per in of the film and dried.
  • An ordinary color silver halide photosensitive emulsion was coated on the other undercoated surface of the film and a protective gelatin layer was formed on the photosensitive layer according to a customary method to obtain a photosensitive material.
  • the formed photosensitive material was wound in such a manner that the front surface was contacted with the back surface and it was allowed to stand in this state at a temperature of 50C. and a relative humidity of 80% for 5 hours. No sticking was observed between th anti-halation layer and the photosensitive layer. Further, even when the above photosensitive material was allowed to stand still at a temperature of 30C. and a relative humidity of for 6 months, no trouble was brought about.
  • EXAMPLE 3 A silver halide emulsion for the Roentgen photography was coated on both undercoated surfaces of a polyethylene terephthalate film and dried. A protective gelatin layer was formed on either of the photosensitive layers. Then, a water-methanol solution l:l) containing 0.5 weight of the exemplified compound (9) (average molecular weight about 8,000; m about n about 20) and 0.2 weight of a 4-nonylphenolformalin resin (degree of polymerization of about 50) added with 30 moles of ethylene oxide was coated on both the surfaces of the above photosensitive material in an amount of IS cc per m of the film, and dried to obtain a photosensitive material for the Roentgen photography according to this invention.
  • a water-methanol solution l:l containing 0.5 weight of the exemplified compound (9) (average molecular weight about 8,000; m about n about 20) and 0.2 weight of a 4-nonylphenolformalin resin (degree of
  • the obtained photosensitive material was inserted between two sheets of a sensitizing paper having a cellulose estertreated surface and allowed to stand still at a temperature of 50C. and a relative humidity of 80% for 1 day. Then, it was put into a cassette and packed therein by application of a pressure. Then, the packed photosensitive material was allowed to stand still for 1 day, and it was taken from the cassette and covered with a lead plate. Then, it was exposed to X-rays and developed.
  • the undercoating solution was coated on one surface of a biaxially stretched polyethylene terephthalate film having a thickness of I00 u at a rate of m/min in a thickness of 15 u by means of a roll coater. Then, the drying was conducted at 95C. for 1 minute and 30 seconds.
  • An undercoating solution prepared in the same manner as above except that 0.02 g of bis-hexylene ethyleneimino ureide was further added was coated on the other surface of the film in the same manner as above.
  • a silver halide emulsion for the electronic recording was formed on the formed undercoating to form a photosensitive material.
  • the photosensitive material was cut into a width of 8.75 mm and 50 m of the photosensitive material was wound on one reel.
  • the wound photosensitive material was allowed to stand still at a temperature of 40C. and a relative humidity of 85% for 1 day. No sticking was observed and the photographic characterristics were not degraded at all.
  • a photosensitive material for formation of cut film comprising a cellulose triacetate film having a thick ness of 200 [1-, a layer of a silver halide emulsion forth monochromatic photography formed on one surface 0 the film and a gelatin layer formed on the other surfacl was prepared, and 2% aqueous solution containing 0. g of the exemplified compound 13) (average molecu lar weight about 6,000; m about 35; n, about 20 n about 45) and 0.1 g of gelatin was coated on th gelatin layer of the above photosensitive material anc dried.
  • cut films of a size of [00 mm 125 mrr were cut from the above photosensitive materials, anc about l0 of such cut films were lapped in such a manner that the front surface of one cut film was contacted with the back surface of another cut film.
  • a glass plate was placed on the lapped cut films and a load of 5 Kg was imposed on the glass sheet. In this state, the cut films were allowed to stand still at a temperature of C. and a relative humidity of for 5 hours.
  • a silver halide photosensitive material which comprises at least one of the outermost layers containing, as the major component, a polymer which has monomer units having a guanidinoimino or gaunidinoamino group in the side chain.
  • a silver halide photosensitive material according to claim I wherein the amount of said polymer is 0.001 to lg per m" of the photosensitive material.
  • a silver halide photosensitive material which comprises at least one of the outermost layers containing, as the major component, a polymer represented by the following formula:
  • m and :1 indicate the mole percentages of the copolymerizable monomer components respectively, the sum of m and n being m being within a range of from about to l0()% and n being within a range of about 80 to 0%.

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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Silver Salt Photography Or Processing Solution Therefor (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
US400237A 1972-09-28 1973-09-24 Silver halide photosensitive material Expired - Lifetime US3893861A (en)

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Application Number Priority Date Filing Date Title
JP47096592A JPS52372B2 (enrdf_load_stackoverflow) 1972-09-28 1972-09-28

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US (1) US3893861A (enrdf_load_stackoverflow)
JP (1) JPS52372B2 (enrdf_load_stackoverflow)
BR (1) BR7307599D0 (enrdf_load_stackoverflow)
DE (1) DE2348636A1 (enrdf_load_stackoverflow)
GB (1) GB1440644A (enrdf_load_stackoverflow)

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2882156A (en) * 1955-12-19 1959-04-14 Eastman Kodak Co Basic mordants derived from the reaction of carbonyl containing polymers and aminoguanidine and their use

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2882156A (en) * 1955-12-19 1959-04-14 Eastman Kodak Co Basic mordants derived from the reaction of carbonyl containing polymers and aminoguanidine and their use

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Publication number Publication date
GB1440644A (en) 1976-06-23
BR7307599D0 (pt) 1974-09-05
DE2348636A1 (de) 1974-04-11
JPS52372B2 (enrdf_load_stackoverflow) 1977-01-07
JPS4955321A (enrdf_load_stackoverflow) 1974-05-29

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Owner name: KONICA CORPORATION, JAPAN

Free format text: RELEASED BY SECURED PARTY;ASSIGNOR:KONISAIROKU PHOTO INDUSTRY CO., LTD.;REEL/FRAME:005159/0302

Effective date: 19871021