US3510297A - Process for producing negative transparencies - Google Patents

Process for producing negative transparencies Download PDF

Info

Publication number
US3510297A
US3510297A US547728A US3510297DA US3510297A US 3510297 A US3510297 A US 3510297A US 547728 A US547728 A US 547728A US 3510297D A US3510297D A US 3510297DA US 3510297 A US3510297 A US 3510297A
Authority
US
United States
Prior art keywords
transparent
areas
barrier material
diazo
light
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
US547728A
Other languages
English (en)
Inventor
Clifford E Herrick Jr
Ulo Vahtra
Meredith David Shattuck
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
International Business Machines Corp
Original Assignee
International Business Machines Corp
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by International Business Machines Corp filed Critical International Business Machines Corp
Application granted granted Critical
Publication of US3510297A publication Critical patent/US3510297A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G5/00—Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
    • G03G5/02—Charge-receiving layers
    • G03G5/04—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
    • G03G5/05—Organic bonding materials; Methods for coating a substrate with a photoconductive layer; Inert supplements for use in photoconductive layers
    • 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
    • G03C1/675—Compositions containing polyhalogenated compounds as photosensitive substances
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
    • G03C1/00—Photosensitive materials
    • G03C1/72—Photosensitive compositions not covered by the groups G03C1/005 - G03C1/705
    • G03C1/73—Photosensitive compositions not covered by the groups G03C1/005 - G03C1/705 containing organic compounds
    • G03C1/732—Leuco dyes
    • 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
    • G03C5/18—Diazo-type processes, e.g. thermal development, or agents therefor
    • 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
    • G03C5/60—Processes for obtaining vesicular images
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G13/00—Electrographic processes using a charge pattern
    • G03G13/22—Processes involving a combination of more than one step according to groups G03G13/02 - G03G13/20
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G5/00—Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
    • G03G5/02—Charge-receiving layers
    • G03G5/04—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
    • G03G5/06—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being organic
    • G03G5/0664—Dyes
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G5/00—Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
    • G03G5/02—Charge-receiving layers
    • G03G5/04—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
    • G03G5/06—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being organic
    • G03G5/0664—Dyes
    • G03G5/0675—Azo dyes
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G5/00—Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
    • G03G5/153—Charge-receiving layers combined with additional photo- or thermo-sensitive, but not photoconductive, layers, e.g. silver-salt layers
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G9/00—Developers
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G9/00—Developers
    • G03G9/08—Developers with toner particles

Definitions

  • An electrophotographic process for producing negative transparencies comprising the steps of: forming an electrostatic charge pattern on a photo-sensitive member containing an essentially transparent photoconductive insulating layer and a component capable of responding to treatment with an agent to convert the member from transparent to opaque; developing the electrostatic charge pattern with an essentially transparent barrier material not convertible to opaque when said member is treated with said agent; and treating the photosensitive member with said agent so that, through the coaction of the component and the agent, the areas of the member not developed with said barrier material are converted from transparent to opaque, but the areas of the member developed with barrier material are prevented from such conversion because of the barrier material, thereby forming a negative transparency.
  • This invention relates to a method for producing photographic transparencies or translucencies and, more particularly, to electrostatic and electrophotographic methods especially suited for producing negative photographic transparencies or translucencies from either a negative or positive original.
  • electrophotography herein defined to include both electrophotographic and electrostatic methods, i.e. electrostatic images formed with and without an exposure step
  • electrophotography i.e. electrostatic images formed with and without an exposure step
  • greater field intensity, or sharp voltage contrast is present at the edges of an electrostatic image so that, when the electrostatic image is developed without a development electrode, the large image areas of continuous toning are highly developed at the edges and almost completely undeveloped in the central portions.
  • negative transparencies or translucencies which have many large image areas are unusable when developed by, for example, the cascade technique without a development electrode.
  • An imaging process for producing negative transparencies of limited resolution is known in which a uniform layer of charged powder on the surface of a conductive transparent material is removed by the electrostatic fields of an electrostatic image on a photoconductor.
  • the transfer of the powder occurs when the uniformly dusted transparent conductive plate is brought into contact with the electrostatic image and a DC. potential is applied between the two surfaces.
  • a DC. potential is applied between the two surfaces.
  • this process is capable of producing negative transparencies from positive originals, it is very cumbersome and results in low resolution transparencies. Further, it requires large amounts of toner, is susceptible to pinholes and uses a development electrode effect.
  • the developed image of unpigment toner on a photoconductor is transferred to an expendable transparent material having a pressure sensitive adhesive coating.
  • the adhesive properties of the coating are destroyed in the transferred image areas.
  • the adhesive sheet is next placed into contact with a second expendable material having a thin releasable layer of high opacity coated on a transparent sheet. After contact has been established, the two layers are separated and the opaque layer is transferred to the sheet in the non-image areas and remains on the first adhesive sheet in the image areas.
  • the first adhesive sheet becomes a negative transparency and the second adhesive sheet becomes a positive transparency. While this process provides high resolution negative transparencies and permits cascade toning, it should be readily apparent that the process requires a multitude of additional steps after the formation of the toner image on the photoconductor.
  • a more specific object of the present invention is to provide a new and improved process for producing electrophotographic negative transparencies in which large areas of continuous toning is not necessary.
  • a further object of the present invention is to provide a new and improved process for producing negative electrophotographic transparencies from the positive originals which requires essentially only one additional step beyond the steps of the electrophotographic process.
  • an electrostatic charge pattern on a photosensitive member containing an essentially transparent photoconductive insulating layer and component capable of responding to treatment with an agent to convert the member from transparent to opaque developing the electro static charge pattern with a transparent or translucent barrier material not convertible to opaque when said member is treated with said agent so that, if the material was opaque, a positive transparency would result, and treating the transparent layer with said agent so that the areas of said member not developed with said barrier material are converted from transparent to opaque, but the areas of the member developed with the barrier material are prevented fom such conversion because of the barrier material, thereby forming a negative transparency.
  • any electrophotographic process may be used in forming the electrostatic image.
  • the process disclosed in U.S. Patent 2,297,691 in which the photoconductive insulating layer is electrostatically charged in the dark and then the charged layer is exposed to a light image to form an electrostatic charge image.
  • a persistent internal polarization or persistent photoconductivity mode of electrophotography such as described in U.S. Patent 2,845,348 and in copending application, Ser. No. 474,977, filed July 26, 1965 could be used.
  • the charge transfer process of U.S. Patent 2,937,943 in which the electrostatic image formed on the photoconductor is transferred to a dielectric sheet, i.e.
  • organic photoconductors and organic dielectrics are both the small molecule and the polymeric photoconductors listed in copending application, Ser. No. 474,977 and US. 3,232,755.
  • a conductive substrate is to be used, it also must be transparent and may be a layer of polyethylene terephthalate coated with a thin layer of aluminum or copper, or may be a layer of NESA glass.
  • the photoconductive layer can be self-supporting or be carried on a non-conductive support if the dual corona charging technique of U.S. Patent 2,922,883 is employed.
  • a number of known electrophotographic development techniques may be used.
  • cascade development of US. Patent 2,618,551, liquid development of US. Patent 2,877,133 and magnetic brush development of US. Patent 2,874,063 are all suitable methods for developing the electrostatic image formed by one of the above electrophotographic processes.
  • the photosensitive member contains, in addition to the photocondu'ctive insulating layer, a component uniformly dispersed in the photoconductive layer or uniformly dispersed throughout a separate layer and capable of responding to an agent for converting the layer in which the component is present from transparent to opaque.
  • the separate layer is sufficiently insulating to support an electrostatic charge, i.e. having a resistivity greater than 10 ohm-cm.
  • the process of the present invention comprises:
  • the following table in general, shows the various photosensitive systems of the present invention and the relationship of the component and barrier material to the agent.
  • alkaline sensitive material such as:
  • diazo compound e.g. 2,5 diethoxy 4 morpholino benzene diazonium fluoborate
  • azo coupler e.g. 2-hydroxy-3-naphtoyl-o-anisidine
  • diazo compound e.g. p-dimethylamino benzene diazonium fiuoborate
  • light sensitive material such as:
  • aryl amine e.g. diphenylamine
  • halo substituted hydrocarbon e.g. carbon tetrabromide
  • triarylmethane dye cyanides e.g. 4,4',4" triamino-triphenyl acetonitrile
  • diazo compound e.g. p-dimethylamino benzene diazonium chloride zinc chloride
  • dye absorbing material such as:
  • alkaline material such as:
  • ultraviolet and visible light e.g. 3000 A.-4800 A.
  • ultraviolet light e.g. 2400 A. to about 3500 A.
  • ultraviolet light e.g. 3000 A.-4000 A.
  • (3) dye such as:
  • barrier material transparent alkaline absorbing, but not sensitive ma- In system (1) of Table I, the electrostatic image on the photosensitive member is developed with a barrier material comprising transparent alkaline absorbing or acidic material which serves as a barrier to an alkaline agent.
  • a number of solid organic acids may be employed as the barrier material and, for example, phenylacetic, malonic, and glycolic carboxylic acids as well as saturated fatty acids with melting points above 43 C. (see Table 15.1 in Fieser and Fieser, Organic Chemistry, 3rd edition) are a few specific acids which may be used.
  • the components of the photosensitive member is an alkaline sensitive substance such as a diazo compound which either is uniformly dispersed throughout the photoconductor layer or is dispersed in a layer overcoating the photoconductor.
  • the alkaline agent preferably is a gas, such as ammonia, and diffuses into the areas of the photosensitive member unprotected by the acidic barrier material to provide the necessary alkaline medium for a reaction between the diazo compound and the azo coupler to form the dye.
  • the alkaline absorbing or acidic barrier material preferably stearic acid
  • the ammonia is absorbed and neutralized so that an alkaline medium is not present for dye formation under these barrier areas. Hence, they remain transparent and a negative transparency results.
  • system 1)(b) of Table I may be employed in which the azo coupler is present with the alkaline agent rather than the diazo compound.
  • the alkaline agent now takes the form of a liquid solution and a semi-wet development step is necessary to form the dye in the areas not covered by the acidic barrier material.
  • the alkaline agent is sodium carbonate and the barrier material is the same as in the system (l)(a) as long as the solvent or solvents for the carbonate and azo coupler do not dissolve the barrier material.
  • sodium phosphate or sodium acetate may be substituted for sodium carbonate.
  • Suitable diazo compounds for both systems (1)(a) and (1) (b) are, as shown by the following formula, un-
  • diazobenzenes can be substituted diazobenzenes, and un-, mono-, di-, and poly-substituted diazo-p-aminobenzenes and diazo-o-aminobenzenes. Also, diazo mercaptobenzenes may be used.
  • diazo compounds examples include l-diazo- 4-ethoxybenzene, 1-diazo-2,S-diethoxybenzene, 4-diazo-2, S-dimethoxy-diphenyl, 1-diazo- 4-dimethylaminobenzene, l diazo-4-methylallylaminobenzene, -1-diazo4- l,3-oxazolidino)benzene, N,N'-bis (4-aminophenyl) piperazine, 9 (p diazophenyl) carbazole, 1 diazo 3 methyl- 4 dimethylaminobenzene, l diazo 2,5 diethoxy -4- dimethylaminobenzene, 1 diazo 4 ethylbenzyl 3- ethoxyaminobenzene, 1 diazo 4 morpholino 2,5- diethoxyaminobenzene, N-4 amino 3' ethoxyphenyl- (1') thiomorpholine and l diazo 4,5 di
  • Suitable couplers are monohydric phenols, catechol and its derivatives, hydroquinone derivatives, trihydroxybenzenes, hydroxy diphenyl derivatives, naphthols, dioxynaphthalene derivatives, diketo'nes, acetonitriles, cyanacetylamides, sulfonamides, alkylmalonamates, pyronones, hydroxy pyridones, 4-oxyquinolones, pyrazolones, and thiophene derivatives. Specific compounds within these classes are listed on pages 220-248 of Light Sensitive Systems by Jaromir Kosar.
  • the color of the resulting dye desired and, hence, the particular coupler selected. will depend on how the negative transparency is utilized. For example, if it is to serve as a master to expose an ultraviolet sensitive material with an ultraviolet light source then the dye should be yellow or sepia. If an incandescent light source is employed to expose a material sensitive to those wavelengths, through the negative master, the dye of the master should be blue or preferably black.
  • the barrier material deposited to develop the electrostatic image on the photosensitive member is a material which will absorb but not be sensitive to (i.e. become colored) the wavelengths of light serving as the agent, while the component of the photosensitive member is sensitive to such wavelengths of light and becomes colored when exposed.
  • the light sensitive material either can be disposed in a layer overcoating the photoconductive layer or be present in the photoconductive layer.
  • the halo substituted hydrocarbon preferably is carbon tetrabromide, but may be iodoform, n-bromosuccinimide, carbon tetrabromide, 2- chloroanthaquinone, tetrabromo o cresol, brominated polystyrene, tetrabromphenolphthalein, 1,2,3,4 tetrabrombutane, 1,2,3,4 tetrachlorobcnzene, carbon tetrachloride, tetrachlortetrahydronaphthalene, 1 chloro 4- nitrobenzene, hexachloroethane. Also, several of these halogenated compounds may be utilized as a mixture in the photosensitive member.
  • the wavelength of light, to which the system (2a) of Table I is sensitive, is dependent not only on the aryl amine, whose sensitivity normally is in the ultraviolet portion of the spectrum, but also the halogenated com pound and the complex formation between them.
  • halogenated methane compounds in which at least one hydrogen has been replaced by iodine are sensitive in the spectral range from 5100 A. and 5500- A.
  • the spectral range of bromated compounds is 3900 A.4000 A.
  • chlorinated derivatives are sensitive to radiation of 3000 A. Therefore, the usable portion of the spectrum ranges from 3000 A.5000 A.
  • the barrier material or light absorbing material must be selected so as to match the wavelength sensitivity of the aryl amine-halo compound or must broadly absorb 3000 A.5500 A.
  • the photosensitive member is sensitive to wavelengths of light within the range of 3300 A.
  • the barrier material may be one of the following light absorbers: l,3-di-2-thienyl-2-propen-l-one, Z-naphthalenediazocarboxamide, phenylsalicylate, 2,4-dibenzoylresorcinol, 4,4-oxalyldiresorcinol, butyl-3-umbelliferonecarboxylate, 2,3-bis (3,4-methylenedioxyphenyl) 5-penylpyrrole, 2,2'-dihydroxy-4,4-dimethoxybenzophenone and 2,2'4-trihydroxy 4-methoxy-benzophenone. Other com pounds which will absorb wavelengths of light within 3000 A.5500 A.
  • 2,4,6-trinitroanisole 2,4,6-trinitrophenol
  • 4-nitro-N,N-diethylaniline 2-nitrodiphenylamine
  • 4 nitrodiphenylamine 2,2,4 trinitrodiphenylamine
  • 2,4,6-trinitrodiphenylamine 4-nitrocatechol
  • the component or light sensitive material of the photosensitive member is a trarylmethane-dye cyanide which again either is dispersed throughout the photoconductve layer or present in an overcoated layer.
  • the agent is light, more specifically ultraviolet light
  • the barrier material is an ultraviolet light absorbing material.
  • triarylmethane-dye cyanides useful as the component or light sensitive material are 4,4,4"-triamino-triphenylacetonitrile, 4,4',4"-triamino 3-methyl-triphenylacetonilrile, Aurin cyanide, Ethyl Green cyanide, Xylene Blue VS cyanide, Light Green SF cyanide.
  • Acid Violet 6B cyanide Soluble Blue cyanide, 4,4-bis-dimethylamino- 2"-chloro-triphenylacetonitrile, Helvetia Green cyanide, Acid Fuchsine cyanide, N,N,N,N',N",N"-hexa 2-hydroxyethyl rosaniline cyanide, Acid Green l6-cyanide, Naphthalene Green V-cyanide.
  • These dye cyanides are sensitive to wavelengths of light in the range 2400 A. to 3500 A.
  • Materials which absorb in the 2400 A.3800 A. range and can serve as the barrier material are phenylsalicylate, 4-tert-butyl phenylsalicylate, S-chloro 2-hydroxybenzophenone, 2,4 dibenzoylresorcinol, 2 hydroxy 4- methoxy-benzophenone, 2,2'-dihydroxy 4,4'-dimethoxybenzophenone, and 2(2'-hydroxy-5-methylphenyl)benzotriazole.
  • the vesicular process such as described initially in US. 2,750,292 and subsequent vesicular patents, is used to render opaque the areas of the photosensitive member not covered with barrier material.
  • the member contains, in addition to the photoconductor, a gas generating material such as daizo compound of benzene or naphthalene.
  • Examples of specific gas generating materials are p-diazodimethylaniline zinc chloride, p-diazodiethylaniline zinc chloride; p-diazodiphenylamine sulfate, p-diazoethylhydroxyethylaniline zinc chloride, 1-diazo-2-oxynaphthalene-4-sulfonate, 4- benzoylamino 2,5-diethoxybenzene diazonium chloride, p-chlorobenzenesulfonate of 4-diazo-2-methoxy-l-cyclohexylaminobenzene, 7-dimethylamino 8-methoxy-3-oxodihydro 1,4-thiazine 6-diazonium fiuoroborate, l-dimethylamino 4-naphthalene diazonium fiuoroborate, 3- 0x0 7-dialkylaminobenzothiazine diazonium borofluorides,
  • a commercial electrophotographic toner may be used to develop the electrostatic image and is removed after the necessary exposure to generate the gas in the photosensitive member. After such exposure, the toner may be removed and the photosensitive member heated to form the vesicular structure and render the exposed area opaque. Depending on the particular gas generating material, the heating step may range from 80 to 150 C.
  • the agent is a dye and the component is the surface of the photosensitive member which is such that it readily absorbs the dye agent.
  • the barrier material does not absorb the dye and remains transparent.
  • the dye absorption-non absorption depends whether the substance being dyed contains polar or non-polar functional groups. That is, the dye contains polar groups and is attracted to the substance to be dyed if it also contains polar groups. Therefore, the photoconductor, if it is a polymer, or the polymeric binder for the photoconductor, should contain polar groups whereas the barrier material should not.
  • examples of polymeric binders are polyvinyl formal and polyvinyl butral while the examples of the barrier material are polystyrene and polyalkenes (polyethylene, polypropylene, etc.),
  • the photoconductor will be sufiiciently polar so that the binder and the barrier material can be the same polymer.
  • dyes which are useful are diand triphenylmethane dyes; such as Auramine 0 (Cl. 41000, Color Index, second edition), Malachite Green (C1. 4200), Para Rosaniline (CI. 42500), Methyl Violet (C.I. 42535), Aurine (CI. 43800), and Victoria Blue (CI. 44045); xanthene dyes; such as Rhodomine B (CI. 45170); acridine dyes, such as Acridine Orange (CI. 46005); and Thiazine dyes, such as Methylene Blue (C1. 52015).
  • Auramine 0 Cl. 41000, Color Index, second edition
  • Malachite Green C1. 4200
  • Para Rosaniline CI. 42500
  • Methyl Violet C.I. 42535
  • Aurine CI. 43800
  • Victoria Blue CI. 44045
  • xanthene dyes such as Rhodomine B (CI. 45170)
  • the barrier material can be formed into toner by grinding the material into fine particles and dispersing the particles with a carrier such as glass beads for cascade development, a dielectric liquid for liquid development and ferromagnetic particles for magnetic brush development.
  • the toner particles can be dissolved in a solution and the solution dispersed in a dielectric liquid immiscible with the solution to form an emulsion type liquid toner for liquid development.
  • the barrier material may not be fusable at low temperatures, i.e. between 60 C. and 120 C. or at least below the decomposition temperature of the component, or does not have the .proper electrostatic properties, i.e. triboelectric property.
  • a solid solution is formed and consists of the barrier material and a material with a low melting point and/or the proper triboelectric property, for example, polystyrene, butyl methacrylate-styrene copolymer and polymethylmethacrylate. This solid solution then is ground to fine particles to serve as a toner.
  • a photosensitive composition was prepared by the addition of 0.04 gram of 3,5-dinitrobenzoic acid to 7% solution of polyvinyl carbazole in dichloroethane. To this was added 0.07 gram of 2,5-diethoxy-4-morpholino-benzone diazonium borofluoride and 0.07 gram of Z-hydroxy- 3-naphthoyl-o-anisidine. The composition was coated on an aluminum coated polyethylene terephthalate substrate.
  • the latent electrostatic image was developed by immersion into trichlorotrifiuoroethane containing suspended finely powdered stearic acid. This resulted in a transparent film.
  • the film was suspended in an ammonia atmosphere and, where the ammonia was able to diffuse into the film, i.e. the undeveloped stearic acid areas, these areas formed a blue color to provide a negative film of the positive original.
  • the film was given a short ultraviolet exposure.
  • a photosensitive film was prepared by coating a polyvinyl carbazole photoconductive layer containing 0.25% Malachite Green oxalate and 4% 3,5-dinitrobenzoic acid on an aluminum coated polyethylene terephthalate substrate. On top of the photoconductive layer was coated a thin layer of polyvinyl pyrrolidone containing 10% of tris-[4-(2-hydroxyethyl)aminophenyl] acetonitrile trihydrochloride. The film was charged with positive corona of 7500 volts after heating for one minute at 100 C. The film was then exposed through a positive master to a 25 watt incandescent lamp at 30 centimeters for one second.
  • an ultraviolet light absorber consisting of finely powdered 2,2-dihydroxy-4,4'- dimethoxy benzophenone and isomers, and glass beads were cascaded over the film containing the electrostatic image. After a few seconds of heating to melt the ultraviolet light absorber, the film was exposed to General Electric UA-Z mercury are at 10 inches for five seconds to produce a negative image containing a dark blue background with light green image areas.
  • a photosensitive film was prepared by dissolving 2 grams of 1,3,S-triphenylpyrazoline and 0.1 gram of 3,5- dinitrobenzoic acid in 10 ml. of 1,2-dichloroethane. To this was mixed a ZO-gram solution of 10% polyvinyl formal in 60 parts of toluene and 40 parts of ethanol. The resulting mixture was coated on an aluminum coated polyethylene terephthalate substrate with a 5 mil gap on the doctor blade. The photosensitive film thus prepared was electrostatically charged with a corona unit at plus 7000 volts and exposed through a positive master to a 40 watt incandescent lamp at 12 inches for 5 seconds.
  • the electrostatic charge pattern was developed by cascading a developer mixture of carrier with 1% of finely divided low melting polystyrene as toner over the electrostatic image.
  • the polystyrene powder was attracted to the electrostatic image and was fused to the photosensitive film by heating at C. for about five seconds.
  • the background or undeveloped areas of the almost invisible image was converted to opaque by immersion of the film in a 3% solution Victoria Blue BO base in ethanol for 10 seconds. After immersion, the photoconductor was reheated for 5 seconds at 150 C. In the areas where the polystyrene was deposited the dye solution did not penetrate the film and remained transparent. In the areas not developed with styrene, the film was dyed a deep blue and resulted in a negative of the original positive image.
  • EXAMPLE IV A solution of 0.76 gram of polyvinyl carbazole, 40 mg. of 3,5-dinitrobenzoic acid and 3 mg. of Malachite Green oxalate in 10 ml. of 1,2-dichloroethane was prepared. Using a polyethylene terephthalate substrate containing a transparent film of aluminum, the prepared solution was coated on the substrate using a 7 mil gap on the doctor blade. The photoconductor was overcoated with a solution obtained by mixing 10 ml. of 15% solution vinylidene chloride-acrylonitrile copolymer in 2-butanone and a solution of 0.3 g. of p-dimethylamino benzene diazonium chloride zinc chloride in ml.
  • the overcoat was coated with 3 mil doctor blade gap.
  • the thus prepared film was electrostatically charged with a positive 7000 volt corona unit and then exposed through a positive master to a 40 watt incandescent lamp at 12 inches for two seconds.
  • the electrostatic charge image was developed with particles of 2,2-dihydroxy-4,4-dimethoxy benzophenone and fused. With the toner particles fused to the electrostatic image or the unexposed portions of the film, the film was exposed to a General Electric UA-2 mercury arc for 40 seconds. After this exposure, the film was heated by passing it through rollers at 115 C. In the areas where the film had been exposed to ultraviolet radiation of the mercury arc, a vesicular structure formed in the film. Thus, when the film was viewed with a projected light, a negative image of the positive original was obtained due to scattering of the light by the vesicular structure in the background areas.
  • said alkaline sensitive material is a diazo compound and an azo coupler compound
  • said alkaline material is selected from the group consisting of ammonia and ammonia-generating precursors
  • said alkaline absorbing material is an acidic compound.
  • diazo compound is 2,5-diethoxy-4-morpholino-benzene diazonium borofiuoride and said azo coupler is 2-hydroxy-3-naphthanolo-anisidine, said alkaline material is ammonia, and said acidic barrier material is finely powdered stearic acid.

Landscapes

  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Photoreceptors In Electrophotography (AREA)
  • Developing Agents For Electrophotography (AREA)
  • Dry Development In Electrophotography (AREA)
US547728A 1966-05-05 1966-05-05 Process for producing negative transparencies Expired - Lifetime US3510297A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US54772866A 1966-05-05 1966-05-05

Publications (1)

Publication Number Publication Date
US3510297A true US3510297A (en) 1970-05-05

Family

ID=24185893

Family Applications (1)

Application Number Title Priority Date Filing Date
US547728A Expired - Lifetime US3510297A (en) 1966-05-05 1966-05-05 Process for producing negative transparencies

Country Status (6)

Country Link
US (1) US3510297A (en:Method)
JP (1) JPS523299B1 (en:Method)
BE (1) BE695596A (en:Method)
DE (1) DE1572346C3 (en:Method)
FR (1) FR1517306A (en:Method)
GB (1) GB1155546A (en:Method)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4150985A (en) * 1974-12-13 1979-04-24 International Business Machines Corporation Image forming process involving phase change
US4291109A (en) * 1979-11-26 1981-09-22 Eastman Kodak Company Additive color imaging using a silverless recording element
US4871640A (en) * 1987-05-15 1989-10-03 Minolta Camera Kabushiki Kaisha Method for producing an original for use in an overhead projector

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3784743A (en) * 1972-08-23 1974-01-08 Bell Telephone Labor Inc Parallel data scrambler

Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2939787A (en) * 1957-03-01 1960-06-07 Rca Corp Exposure of photochemical compositions
US3038799A (en) * 1958-01-13 1962-06-12 Commw Of Australia Method of reversing the image in xerography
US3083117A (en) * 1957-06-14 1963-03-26 Schmiedel Ulrich Process of developing electrostatic images
US3104169A (en) * 1956-06-27 1963-09-17 Commw Of Australia Production of printing blocks, resists, transparencies, prints and the like by electro-deposition
US3113022A (en) * 1959-02-26 1963-12-03 Gevaert Photo Prod Nv Electrophotographic process
US3212890A (en) * 1955-09-30 1965-10-19 Minnesota Mining & Mfg Photoconductive element for use in electrophotography containing a heavy metal soap of a long chain fatty acid; and process for using same
US3226227A (en) * 1960-09-02 1965-12-28 Rca Corp Method of producing a solvent-resistant pattern using developed electrostatic image formation techniques
US3236639A (en) * 1959-09-04 1966-02-22 Azoplate Corp Two component partially removable electrophotographic developer powder and process for utilizing same
US3272644A (en) * 1963-07-31 1966-09-13 Dennison Mfg Co Development of latent electrostatic images with crystalline toners
US3313626A (en) * 1962-08-01 1967-04-11 Russeli H Whitney Process of making a lithographic printing plate

Patent Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3212890A (en) * 1955-09-30 1965-10-19 Minnesota Mining & Mfg Photoconductive element for use in electrophotography containing a heavy metal soap of a long chain fatty acid; and process for using same
US3104169A (en) * 1956-06-27 1963-09-17 Commw Of Australia Production of printing blocks, resists, transparencies, prints and the like by electro-deposition
US2939787A (en) * 1957-03-01 1960-06-07 Rca Corp Exposure of photochemical compositions
US3083117A (en) * 1957-06-14 1963-03-26 Schmiedel Ulrich Process of developing electrostatic images
US3038799A (en) * 1958-01-13 1962-06-12 Commw Of Australia Method of reversing the image in xerography
US3113022A (en) * 1959-02-26 1963-12-03 Gevaert Photo Prod Nv Electrophotographic process
US3236639A (en) * 1959-09-04 1966-02-22 Azoplate Corp Two component partially removable electrophotographic developer powder and process for utilizing same
US3226227A (en) * 1960-09-02 1965-12-28 Rca Corp Method of producing a solvent-resistant pattern using developed electrostatic image formation techniques
US3313626A (en) * 1962-08-01 1967-04-11 Russeli H Whitney Process of making a lithographic printing plate
US3272644A (en) * 1963-07-31 1966-09-13 Dennison Mfg Co Development of latent electrostatic images with crystalline toners

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4150985A (en) * 1974-12-13 1979-04-24 International Business Machines Corporation Image forming process involving phase change
US4291109A (en) * 1979-11-26 1981-09-22 Eastman Kodak Company Additive color imaging using a silverless recording element
US4871640A (en) * 1987-05-15 1989-10-03 Minolta Camera Kabushiki Kaisha Method for producing an original for use in an overhead projector

Also Published As

Publication number Publication date
DE1572346A1 (de) 1970-02-26
DE1572346C3 (de) 1975-03-20
BE695596A (en:Method) 1967-09-01
DE1572346B2 (de) 1974-08-01
FR1517306A (fr) 1968-03-15
JPS523299B1 (en:Method) 1977-01-27
GB1155546A (en) 1969-06-18

Similar Documents

Publication Publication Date Title
US3037861A (en) Electrophotographic reproduction material
US3383993A (en) Photoelectrophoretic imaging apparatus
US3799773A (en) Electrophotographic process employing a photochromic compound and transparent toner
US4146707A (en) Heterocyclic ethenyl or vinyl heterocyclic or aromatic compounds for migration imaging processes
US3556781A (en) Migration imaging process
US3525612A (en) Electrophotographic reproduction process employing a light sensitive material and a photoconductive material
US3206306A (en) Material for electrophotographic purposes
US3316088A (en) Process of electrophotography based on electrophotolytic reactions and element therefor
US3380823A (en) Photocopying method
US3681066A (en) Process whereby a diazo-containing material exhibits an imagewise change in triboelectric charging properties
US3510297A (en) Process for producing negative transparencies
US3448029A (en) Electrophoretic imaging process using 8,13-dioxodinaphtho - (2,1 - b; 2',3'-d) - furan-6-carboxamide pigments
US3615412A (en) Fluorene type compounds as organic photoconductors
US3458310A (en) Electrophotographic color printing
GB1223020A (en) Method of preparing dye-bearing matrixes
US3723110A (en) Electrophotographic process
US3627527A (en) Organic photoconductors sensitized by dyes which exhibit spectral absorption shifts on heating
US3912505A (en) Color imaging method employing a monolayer of beads
JPH03264978A (ja) ゼロプリンティング方法
US3677750A (en) Photoelectrosolographic imaging process
US3681064A (en) Photoelectrophoretic imaging process employing multicomponent electrically photosensitive particles
US3414409A (en) Particle transfer
US3585026A (en) Treatment of background areas of developed electrophotographic elements with carboxy substituted triarylamine photoconductors with an alkaline medium to reduce opacity
US4007042A (en) Migration imaging method
US3504969A (en) Imaging apparatus