US3870525A - Process for producing photographic film having a magnetizable layer thereon and such a photographic film - Google Patents

Process for producing photographic film having a magnetizable layer thereon and such a photographic film Download PDF

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Publication number
US3870525A
US3870525A US354055A US35405573A US3870525A US 3870525 A US3870525 A US 3870525A US 354055 A US354055 A US 354055A US 35405573 A US35405573 A US 35405573A US 3870525 A US3870525 A US 3870525A
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United States
Prior art keywords
compound
layer
groups
dispersion
weight
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US354055A
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English (en)
Inventor
Nobuo Yamamoto
Hideo Kawaguchi
Katsuharu Furukawa
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Fujifilm Holdings Corp
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Fuji Photo Film Co Ltd
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Publication of US3870525A publication Critical patent/US3870525A/en
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Classifications

    • G—PHYSICS
    • G11—INFORMATION STORAGE
    • G11B—INFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
    • G11B5/00—Recording by magnetisation or demagnetisation of a record carrier; Reproducing by magnetic means; Record carriers therefor
    • G11B5/62—Record carriers characterised by the selection of the material
    • G11B5/633—Record carriers characterised by the selection of the material of cinematographic films or slides with integral magnetic track
    • 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
    • G03C1/91—Photosensitive materials characterised by the base or auxiliary layers characterised by subbing layers or subbing means
    • 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
    • G03C5/00—Photographic processes or agents therefor; Regeneration of such processing agents
    • G03C5/12—Cinematrographic processes of taking pictures or printing
    • G03C5/14—Cinematrographic processes of taking pictures or printing combined with sound-recording

Definitions

  • the present invention relates to a process for producing photographic film having a magnetizable layer thereon and to such a film. More particularly, it relates to a process for providing on a movie film a sound track composed of a magnetic substance and to such a movie film.
  • a magnetizable layer has been applied to a movie film by applying a dispersion of a magnetizable substance to a development-processed movie film.
  • this process has the defect that since images are first recorded and then sound is recorded, images and sound cannot be recored at the same time. Therefore, with movie film having previously provided thereon a magnetizable layerit has been desired to remove the above-described defect, i.e.,-to enable one to record both images and sound at the same time.
  • an antihalation layer is provided as a backing ,layer on a movie film, which antihalation layer can be removed with ease in the alkali development processing of the film.
  • the present invention relates to a process for strongly adhering a magnetizable layer to an antihalation layer on a movie film, where the antihalation layer at the portion on which the magnetizable layer has been coated is rendered insoluble in the alkali development processing used for such movie films, and to movie films thus produced.
  • the magnetizable layer in provided a magnetizable layer on a lightsensitive movie film, can be strongly adhered to the antihalation layer to the extent that the magnetizable layer is not removed in the development processing by applying a dispersion of a magnetic substance onto the antihalation layer after adding to the dispersion a compound having at least 2 isocyanato groups or thioisocyanato groups, or by previously processing the portion of the antihalation layer where the magnetizable layer is to be coated with a solution containing such a compound.
  • Preferred compounds within this class have from 2 to 4 isocyanato groups or thioisocyanato groups. This is because at the present time it is difficult to commercially obtain compounds have more than 4 isocyanato groups or thioisocyanato groups at reasonable cost.
  • alkali soluble resins such as cellulose esters of dicarboxylic acids or vinyl copolymers containing maleic anhydride.
  • cellulose esters of dicarboxylic acids are cellulose acetate phthalate, cellulose acetate maleate, hydroxyalkyl alkyl cellulose tetrahydrophthalate, hydroxyalkyl alkyl cellulose hexahydrophthalate (alkyl moiety thereof having from I to 4 carbon atoms and including a methyl, ethyl, propyl or butyl), and the like.
  • vinyl copolymers containing maleic anhydride are maleic anhydride-styrene copolymers, maleic anhydride-styrene derivative c0- polymers, maleic anhydride-alkyl acrylate copolymers, maleic anhydride-alkyl methacrylate copolymers (alkyl moiety thereof having from 1 to 4 carbon atoms and including a methyl, ethyl, propyl and butyl groups), and the like.
  • styrene derivatives include methylstyrene and p-chlorostyrene.
  • the dispersion for use in forming the antihalation layer suitable comprises 0.1 2% by weight of amixture of carbon black and the above described binder (mixing ratio: 10 parts by weight l5 50 parts by weight), balance organic solvent.
  • the average particle size of the carbon black is preferably 20 30 mg.
  • the present invention is especially effective in the case wherein there is used, as the binder for the antihalation layer, a copolymer ofmaleic anhydride and styrene, a styrene derivative, an alkyl acrylate (alkyl moiety having 1 4 carbon atoms), an alkyl methacrylate (alkyl moiety having 1 4 carbon atoms) or the like, cellulose acetate phthalate, cellulose acetate maleate, hydroxyalkyl alkyl cellulose tetrahydrophthalate (alkyl moiety having I 4 carbon atoms), hydroxylakyl alkyl hexahydrophthalate (alkyl moiety having 1 4 carbon atoms), etc., with the copolymerization ratio of the vinyl copolymer containing meleic anhydride being 121, and preferred styrene derivatives including, for example, methylstyrene, pchlorostyrene, etc.
  • An antihalation layer to be provided on the surface of a photographic film opposite to the surface on which a light-sensitive silver halide emulsion layer is coated is designed to be alkali soluble.
  • the antihalation layer is provided in order to prevent diffused reflection of incident rays upon photographing.
  • the antihalation layer is designed so that it will be dissolved and removed in the step of photographic processing, particularly, development processing (the developer being alkaline). After such treatment, the film becomes transparent.
  • the antihalation layer is rendered alkali insoluble by adding a compound or compounds containing isocyanato groups or thioisocyanato groups to the magnetic recording layer, or, by processing before coating the magnetic recording layer, only the portion of the antihalation layer on which the magnetic recording layer is to be coated is rendered alkali insoluble.
  • the carboxyl groups are not in a salt form while contained in the antihalation layer, and are converted to a COOM (M alkali) type salt in alkali solution (i.e., upon development processing).
  • COOM M alkali
  • the antihalation layer becomes alkali soluble and is delaminated from the film. Therefore, carboxyl groups are not in a salt form before treating with an alkali solution.
  • the amount may be less since the isocyanato or thioisocyanato compound penetrates rapidly together with the solvent.
  • the compound is preferably added to the dispersion of magnetic substance in an amount of 0.05% to 7% by weight, based on the total weight of the magnetic dispersion by weight).
  • the processing in the case of processing the antihalation layer prior to providing the magnetizable layer, it is desirable to conduct the processing with a solution containing 0.05% 10% (by weight) of the compound, based on the total weight of the coating solution by weight).
  • the dried thickness of the magentic layer is about 7 to about 13 microns.
  • the amount of compound in g/cm can be calculated from both the amount added to the magnetic dispersion and the thickness described above.
  • the antihalation layer is processed with a soluabout l5 to about 45 wt
  • ferromagnetic powder(s) preferably 40 wt.7r
  • binder about 5 toabout 20 wt.%
  • the ferromagnetic powder can be yFe O y-Fe- 0 containing Co, Fe O Fe O, containing Co, CrO CO-Ni-Fe alloys or mixtures thereof, e.g., as described in Japanese Pat. Nos. 14090/69; 18372/70; 22062/72; 22513/72; 28466/71; 38755/71; 4286/72; 12422/72; 17284/72; 18509/72; 18573/72; and the like.
  • thermoplastic resin thermosetting resin, (or reaction-type resin) or mixtures thereof are used.
  • thermoplastic resins those having a softening point of less than 150C, a mean molecular weight of about 10,000 to about 200,000 and a eopolymerization degree of about 400 to about 500, such as vinyl chloride-vinyl acetate copolymers, vinyl chloridevinylidene chloride copolymers, vinyl chlorideacrylonitrile copolymers, acrylate-acrylonitrile copolymers, acrylate-vinylidene chloride copolymers, acrylate-styrene copolymers, methacrylate-acrylonitrile copolymers, methacrylate-vinylidene chloride copolymers, methacrylate-styrene copolymers, urethane elastomcrs, nylon-silicone resins, nitrocellulose-polyamide resins, polyvinyl fluorides, vinylidene chlorideacrylonitrile copolymers, butadiene-acrylonitrile copolymers, poly
  • thermosetting resin or reaction-type resin used preferably has a molecular weight of less than about 200,000 in the state of a coating solution and, upon heating after coating and drying, the molecular weight becomes infinite clue to the reaction of condensation, addition etc.
  • these resins those which are not softened or melted before the thermal condensation are preferred.
  • phenol resins epoxy resins, polyurethane thermosettingtype resins, urea resins, melamine resins, alkyd resins, silicone resins, acrylic reactive resins, epoxy-polyamide resins, nitrocellulosemelamine resins, a mixture of a high molecular weight polyester resin and an isocyanate prepolymer, a mixture of a methacrylate copolymer and a diisocyanate prepolymer, a mixture of polyester polyol and a polyisocyanate, urea-formaldehyde resins, a mixture of a low molecular weight glycol/high molecular weight diol/triphenylmethane-isocyanate, polyamide resins and mixtures thereof.
  • Such resins are illustrated in Japanese Pat. Nos. 8103/64; 9779/65; 7192/66; 8016/66; l4275/66; 18179/67; l208l/68; 28023/69; l450l/70; 24902/70; 13103/71; 22065/72; 22066/72; 22067/72; 22072/72; 22073/72; 28045/72; 28048/72; 28922/72; and the like.
  • the magnetic recording layer is formed by dissolving the above-described composition in an organic solvent and applying the resulting coating solution to the antihalation layer.
  • organic solvent used upon-coating there can be employed ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, etc., alcohols such as methanol, ethanol, propanol, butanol, etc.; esters such as methyl acetate, ethyl acetate, butyl acetate, propyl acetate, amyl acetate, ethyl lactate, glycol acetate, monoethyl ether, etc.; ether; glycol ethers such as glycol dimethyl ether, glycol monoethyl ether, dioxane, etc.; aromatic hydrocarbons such as benzene, toluene, xylene, etc.; chlorinated hydrocarbons such as methylene chloride, ethylene
  • any of the solvents used to form the magnetic layer can also be used as solvents in the case where the com pound having at least two isocyanato or thioisocyanato groups is directly applied to the antihalation layer.
  • the preferred solvents used there are ketones, e.g., acetone, methyl ethyl ketone, cyelohexanone, etc., esters, e.g., methyl acetate, ethyl acetate, propyl acetate, butyl acetate, amyl acetate, etc., chlorinated hydrocarbons, e.g., methylene chloride, ethylene chloride, trichloroethane, etc., dioxane, tetrahydrofuran, morpholine, dimethylformamide, methyl cellosolve acetate, aromatic hydrocarbon such as benzene, toluene and xylene and the like, used alone or in suitable combinations.
  • the solvent used can vary depending upon the binder for the the dispersion of the magnetic recording layer, the binder for the antihalation layer and the isocyanato or thiosocyanato compounds. However, a proper solvent can be selected with ease by a person skilled in the art the following points in mind:
  • the solvent should dissolve the binder for the magnetic recording layer
  • the solvent should dissolve the isocyanato or thioisocyanato compound
  • the solvent should dissolve or swell the binder for antihalation layer
  • the solvent should be selected considering a boiling point, etc., suitable for the coating or drying process.
  • All movie film in the Examples comprised standard gelatino silver halide light sensitive emulsions for use in color photography coated on the side of the support opposite the antihalation layer and magnetic recording layer.
  • EXAMPLE 1 and dried at 100C for 10 minutes to form an antihalation layer.
  • the polycondensation ester had the following composition.
  • a polyester was formed by adding an ester exchange reaction catalyst to a mixture of 1 mol. of dimethyl terephthalate, 1.7 moles of ethylene glycol, and 0.8 mol of triethylene glycol.
  • the cellulose ester was cellulose triacetate.
  • the mixture for subbing layer has the following composition. Into a mixed solvent of 52 parts of ethylene dichloride, 8 parts of methylene chloride, 20 parts of methanol, 20 parts of tetrachloroethane and 20 parts of phenol were dissolved 0.2 part of the above-prepared polyester and 0.2 part of the cellulose triacetate, and the coating solution was applied to the surface of the polyethylene terephthalate film at 80C. and dried for 6 minutes at 100C. The procedure is in accordance with Example 1 of U.S. Pat. No. 3,492,122.
  • Nitrocellulose M.W. ca 70000-80000
  • Ferromagnetic 'y-Fe O average particle size: 08 X 0.1 -X 0.1 micron
  • Dibutyl phthalate Ethyl acetate Butyl acetate Cellosolve acetate 10
  • Compound (1V) 0.5
  • EXAMPLE 2 A solution having the following composition was applied to the antihalation layer of a light-sensitive movie 5 film as in Example 1 having the same antihalation layer as in Example 1, and dried at C for 3 minutes.
  • sulting magnetizable layer (ca 8 10p. thick) was alkali-processed as in Example 1 and used in a projector equipped for magnetically recording and reproducing sound and projecting repeatedly 200 times, no damage 40 was observed in the magnetizable layer.
  • EXAMPLE 3 An antihalation layer was formed on a light-sensitive movie film for color photography comprising a cellulose triacetate support by applying a solution having composition (A) and drying the same. Then, a dispersion of a magnetic substance containing different compounds having isocyanato groups or thioisocyanato groups as shown by composition (B) was applied and dried at 40C for 3 minutes.
  • the results obtained by subjecting the resulting films toalkali development processing as in Example 1 were as follows.
  • a process for producing a photographic film having thereon a magnetic recording layer by applying a dispersion of a magnetic substance to an antihalation layer of a llght-sensitive film for cinema. wherein the dispersion contains a compound or compounds, having at least two isocyanato groups or thioisoeyanato groups capable of rendering said antihalation layer alkali insoluble, thereby rendering said antihalation layer alkali insoluble.
  • said dispersion of magnetic substance comprises from about 15 to about 45% by weight of ferromagnetic powder, from about 5 to about 20% by weight of binder, and from about 35 to about 80% by weight of solvent.
  • Compound 0 CN H NC 0 represents a hydrogen atom or wherein the floating NCX group is located at the 0am: or p-position to R, X represents 0 or S, and R repre sents a hydrogen atom or a methyl group,
  • the dried thickness of said processing solution is from about one-tenth to about one-fiftieth of the dried thickness of said magnetic recording layer.
  • a motion picture film having a magnetic recording layer coated on the antihalation layer coating on the film support at the the opposite side of the light sensitive photographic layer, said magnetic recording layer comprising a compound having at least two or more isocyanato groups or thioisoeyanato groups capable of and thereby rendering said antihalation layer alkali insoluble.
  • said magnetic recording layer is coated from a dispersion of the magnetic substance, which comprises from about 15 to about 45% by weight of ferro magnetic powder, from about 5 to about 20% by weight of binder, and from about 35 to about by weight of solvent.
  • a motion picture film claimed in claim 14 wherein said compound has from 2 to 4 isocyanato groups or thioisocyanato groups.
  • a motion picture film claimed in claim 15 wherein said compound is selected from the group consisting of Compounds (1) t0 (XI) below:
  • NCX I NCX wherein the floating NCX group is located at the 0-, mor p-position to R, X represents 0 or S, and R represents a hydrogen atom or a methyl group,
  • said dispersion of magnetic substance comprises from about l5 to about 45% by weight of ferromagnetic powder, from about 5 to about by weight of binder, and from about to about 80% by weight of solvent.
  • NCX Compound (VI) wherein the floating NCX group is located at the o-, mor p-position to R, X represents 0 or S, and R represents a hydrogen atom or a methyl group,

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  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Paints Or Removers (AREA)
  • Manufacturing Of Magnetic Record Carriers (AREA)
  • Magnetic Record Carriers (AREA)
US354055A 1972-04-24 1973-04-24 Process for producing photographic film having a magnetizable layer thereon and such a photographic film Expired - Lifetime US3870525A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP47041123A JPS5128223B2 (enrdf_load_stackoverflow) 1972-04-24 1972-04-24

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US3870525A true US3870525A (en) 1975-03-11

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US (1) US3870525A (enrdf_load_stackoverflow)
JP (1) JPS5128223B2 (enrdf_load_stackoverflow)
DE (1) DE2320657C2 (enrdf_load_stackoverflow)
GB (1) GB1408656A (enrdf_load_stackoverflow)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3999992A (en) * 1971-01-25 1976-12-28 Agfa-Gevaert N.V. Photosensitive element with antihalation layer and magnetic recording strips containing in-benzene disulfofluoride to crosslink antihalation layer
US5254449A (en) * 1990-02-01 1993-10-19 Eastman Kodak Company Photographic element containing thinb transparent magnetic recording layer and method for the preparation thereof
US5254446A (en) * 1990-05-29 1993-10-19 Fuji Photo Film Co., Ltd. Silver halide color negative photosensitive material

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5461717U (enrdf_load_stackoverflow) * 1977-10-03 1979-04-28
JPS575419U (enrdf_load_stackoverflow) * 1980-06-10 1982-01-12

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3649541A (en) * 1969-07-10 1972-03-14 Du Pont Magnetic recording elements containing stabilized chromium dioxide a polyurethane binder and an isocyanate hardening agent
US3689317A (en) * 1968-02-12 1972-09-05 Fuji Photo Film Co Ltd Magnetic recording medium
US3704167A (en) * 1970-06-11 1972-11-28 Fuji Photo Film Co Ltd Process for manufacturing photographic film having a magnetic recording stripe
US3773539A (en) * 1970-03-26 1973-11-20 Konishiroku Photo Ind Method of preparing light-sensitive photographic material with manganese dioxide layer

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1209320B (de) * 1962-08-17 1966-01-20 Eastman Kodak Co Kinefilm mit Tonstreifen
DE2023072A1 (de) * 1970-05-12 1971-12-02 Agfa Gevaert Ag Magnetisches Aufzeichnungsmedium

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3689317A (en) * 1968-02-12 1972-09-05 Fuji Photo Film Co Ltd Magnetic recording medium
US3649541A (en) * 1969-07-10 1972-03-14 Du Pont Magnetic recording elements containing stabilized chromium dioxide a polyurethane binder and an isocyanate hardening agent
US3773539A (en) * 1970-03-26 1973-11-20 Konishiroku Photo Ind Method of preparing light-sensitive photographic material with manganese dioxide layer
US3704167A (en) * 1970-06-11 1972-11-28 Fuji Photo Film Co Ltd Process for manufacturing photographic film having a magnetic recording stripe

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3999992A (en) * 1971-01-25 1976-12-28 Agfa-Gevaert N.V. Photosensitive element with antihalation layer and magnetic recording strips containing in-benzene disulfofluoride to crosslink antihalation layer
US5254449A (en) * 1990-02-01 1993-10-19 Eastman Kodak Company Photographic element containing thinb transparent magnetic recording layer and method for the preparation thereof
US5254446A (en) * 1990-05-29 1993-10-19 Fuji Photo Film Co., Ltd. Silver halide color negative photosensitive material

Also Published As

Publication number Publication date
DE2320657A1 (de) 1973-11-08
JPS494503A (enrdf_load_stackoverflow) 1974-01-16
JPS5128223B2 (enrdf_load_stackoverflow) 1976-08-18
GB1408656A (en) 1975-10-01
DE2320657C2 (de) 1984-01-12

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