US3265497A - Electrophotographic material - Google Patents

Electrophotographic material Download PDF

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Publication number
US3265497A
US3265497A US191389A US19138962A US3265497A US 3265497 A US3265497 A US 3265497A US 191389 A US191389 A US 191389A US 19138962 A US19138962 A US 19138962A US 3265497 A US3265497 A US 3265497A
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Prior art keywords
electrophotographic
layer
image
instance
ketone
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Kosche Horst
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Renker Belipa Fa GmbH
RENKER-BELIPA G M B H Firma
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Renker Belipa Fa GmbH
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    • 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
    • G03G5/0666—Dyes containing a methine or polymethine group
    • G03G5/0668—Dyes containing a methine or polymethine group containing only one methine or polymethine group
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
    • C07C205/45—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by at least one doubly—bound oxygen atom, not being part of a —CHO group
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
    • C07C49/84—Ketones containing a keto group bound to a six-membered aromatic ring containing ether groups, groups, groups, or groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/72—Nitrogen atoms
    • C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/12—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D215/14—Radicals substituted by oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/54—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings condensed with carbocyclic rings or ring systems
    • C07D231/56—Benzopyrazoles; Hydrogenated benzopyrazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
    • C07D333/22—Radicals substituted by doubly bound hetero atoms, or by two hetero atoms other than halogen singly bound to the same carbon atom
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
    • C09B1/16—Amino-anthraquinones
    • C09B1/20—Preparation from starting materials already containing the anthracene nucleus
    • C09B1/22—Dyes with unsubstituted amino groups
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
    • C09D175/04—Polyurethanes
    • 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
    • G03G5/0601—Acyclic or carbocyclic compounds
    • G03G5/0609—Acyclic or carbocyclic compounds containing oxygen
    • 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
    • G03G5/0601—Acyclic or carbocyclic compounds
    • G03G5/0618—Acyclic or carbocyclic compounds containing oxygen and nitrogen
    • 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
    • G03G5/0601—Acyclic or carbocyclic compounds
    • G03G5/062—Acyclic or carbocyclic compounds containing non-metal elements other than hydrogen, halogen, oxygen or nitrogen
    • 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
    • G03G5/0666—Dyes containing a methine or polymethine group
    • G03G5/0672—Dyes containing a methine or polymethine group containing two or more methine or polymethine groups
    • 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
    • G03G5/0666—Dyes containing a methine or polymethine group
    • G03G5/0672—Dyes containing a methine or polymethine group containing two or more methine or polymethine groups
    • G03G5/0674—Dyes containing a methine or polymethine group containing two or more methine or polymethine groups containing hetero rings
    • 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
    • G03G5/10—Bases for charge-receiving or other layers
    • 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
    • G03G5/10—Bases for charge-receiving or other layers
    • G03G5/101—Paper bases
    • 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
    • G03G5/10—Bases for charge-receiving or other layers
    • G03G5/102—Bases for charge-receiving or other layers consisting of or comprising metals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/02—Ortho- or ortho- and peri-condensed systems
    • C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
    • C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
    • C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
    • C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
    • C07C2603/18—Fluorenes; Hydrogenated fluorenes

Definitions

  • electrophotography By the term electrophotography are understood reproducing or recording processes in which latent electric charge patterns are developed.
  • the electrophotographic material is in the form of a backing to which a photoconductive layer is applied, with or without the interposition of auxiliary layers and/ or electrical bar'- rier layers.
  • the phot-oconductive layer is very photosensitive when charged electrically. If the charged electrophotographic material is exposed, a latent charge pattern is produced, the electrostatic charge being reduced or eliminated at those parts of the electrophotographic layer which have been exposed to the light or radiation but remaining at non-irradiated parts.
  • the latent charge pattern can be developed by means of appropriate liquid or solid triboelectric developer systems.
  • the photosensitive photocondu-ctive layer of this electrophotographic material is produced by using special substances which can be called photoconductors without any limitation as to the mechanism of their action.
  • photoconductors for use in electrophotographic layers, such as oxides, sulphides, selenides or arsenides of zinc, lead, cadmium, antimony, tin, and arsenic sulphide, lead chloride, sulphur, anthracene and pyrazoline derivatives, according to Federal German patent specification 1,060,714, 1,3,4-triazole substances according to Federal German patent specification 1,060,260, azomethines according to Federal German patent specification 1,060,712, and poly-nuclear aromatic compounds according to Federal German patent specification 1,060,- 259.
  • these photoconductors are used in combination with a bonding agent of an insulating nature with or without an addition of substances which increase the water-repellant character of the whole.
  • a bonding agent of an insulating nature with or without an addition of substances which increase the water-repellant character of the whole.
  • Ar and Ar denote an aromatic or heterocyclic cyclic system having free electron pairs, such as, for instance, benzene, naphthalene, diphenyl, anthracene, anthraquinone, polynuclear organic cyclic systems such as chrysene, perylene, fluorene or the like or pyridine, thiophene, coumarone, acridine, quinoline, imidazole, pyrazole, indole, pyrimidine or the like;
  • X denotes one or more substituents adhering to the aromatic or heterocyclic ring system, such as H, halogen,
  • phenyl allyl, ethylene which can comprise other substituents, such as -OH, NH OR, NHR, Cl, CN, -SH, COOH, COOR or the like;
  • Y denotes an oxygen or sulphur atom;
  • Ac denotes an acid radical,
  • an organic carboxylic acid such as formyl, acetyl, or benzoyl
  • dior poly-carboxylic acids such as malonic acid, oxalic acid, maleic acid, succinic acid, adipic acid, phthalic acid or terephthalic acid, trimesic acid, tartaric acid, citric acid or their substitution products to be reacted repeatedly with substances having the general Formulae L111; 11 denotes a whole number from 2 to 3; and n denotes a whole number from 1 to 3.
  • the Ar and Ar grouping and the X substituents can be so disposed that symmetrical and asymmetrical compounds are produced which can comprise the X substituents in different ways and a number of times.
  • Ar and Ar
  • ketones having the general Formula I and com may or may not belong to the same cyclic system.
  • Symmetric and asymmetric compounds are suitable as electrophotographically active substances.
  • tertiary aromatic amines having a free p-position and the reaction product is broken down with acids to the ketone.
  • tertiary amines are, for instance, dimethyl aniline, dicthylaniline, ethyl-(B-ox'yethyl)aniline, phenylmorpholine, ethyl-(B-acet-oxyethyl)aniline, u-dimethylaminonaphthaline, phenylpiperidine N acetate, N- methyl-diphenylamine and so on.
  • Substances having the general Formula II are, of course, prepared by condensation of aromatic or heterocyclic methyl ketones with unsaturated aldehydes.
  • Substances having formula III are prepared eitherin the case of symmetrical compoundsby condensation of 2 mol of the aldehyde with 1 mol of acetone, with the action of alkaline or acid condensation agents, orin the case of asymmetrical compounds-by condensation of styrylmethyl-ketones and aldehydes.
  • X substituents which can react with the aldehyde, such substituents are, with advantage, masked before the reaction is performed. 7
  • photoconductors which correspond to the general Formulae I-III and which are reactable with epoxies or isocyanates are reacted, to produce self-adhesive photoconductors, with isocyanate-and/or epoxygroup-containing compounds, with or without an addition of other participants in the condensation which are not photoconductors, to provide electrophotographically active resin-like substances with marked adhesion on metals, ceramic products, papers, plastics, glasses and fabric materials.
  • the following compounds were prepared in accordance with the general Formulae I-III, the number denoting the structural formula:
  • the photoconductors according to the invention differ in their spectral sensitivity.
  • Compound 22 is sensitive only to the spectrum of incandescent light, While with others it is convenient to add sensitisers to adapt the photoconductive layer to the spectral range of desired light sources. As a rule, this increases the photosensitivity.
  • sensitisers there can be used, for instance, the sensitisers conventional in silver halide photography. They can be used in a proportion of from 0.2 to 3% referred to the compounds having the general Formulae I-III.
  • the sensitisers disclosed by French patent specification 1,288,292 are suitable.
  • the photoconductors which correspond to the general Formulae I-III and which comprise X substituents and which can react with epoxies and/or isocyanates, more particularly such photoconductors as have active hydrogen atoms, are, after reaction with isocyanates and/or epoxies, reacted to form self-adhesive photoconductors.
  • Highly photosensitive photoconductive layers can be prepared from these selfadhesive photoconductors without the use of bonding agents. Such layers do not have any of the grain structure of the photoconductor.
  • Photoconductive layers can also the prepared by compounds corresponding to the general Formulae I-III or the self-adhesive photoconductors prepared from such compounds being used in a mixture or in solutions with bonding agents. Other photoconductors, such as zinc oxide, can be added.
  • the bonding agents can be natural and synthetic resins, with or without an addition of plasticisers. A number of bonding agents are disclosed in French patent specification 1,288,392. The bonding agents can either be dissolved in solvents or used as aqueous dispersions, depending upon their properties, in combination with one or more electrophotographically active compounds of the general Formulae I-IH, with or without an addition of sensitising dyes, to produce the photoconductive layer. Bonding agents which in combination with solvents dissolve the photoconductors are convenient.
  • the proportion of electrophotographically active substances corresponding to Formulae I-III to bonding agents can vary within wide limits, and the charging time and photosensitivity can be varied by such proportion being varied; the same can also be used to control the ability to store latent electrostatic charge patterns fora prolonged time.
  • the photosensitivity of the photoconductive layer also depends upon its thickness. A thickness of from 0.002 to 0.1 mm., more particularly from 0.004 to 0.008 mm., is very satisfactory. Above a critical thickness of the layer or emulsion, the image is reversed from positive to negative. This eifect is technically useful for the preparation of reversal material.
  • the preparation which forms the photoconductive layer is applied to an appropriate backing material by some form of conventional treatment, such as lacquering, centrifuging, spraying, electrostatic spraying, printing, coating with coating rollers and scraping oft with doctor devices, dipping, reeling, pressing with grooved dyes, or in the form of a foil, with subsequent lining, or by means of an extruder.
  • some form of conventional treatment such as lacquering, centrifuging, spraying, electrostatic spraying, printing, coating with coating rollers and scraping oft with doctor devices, dipping, reeling, pressing with grooved dyes, or in the form of a foil, with subsequent lining, or by means of an extruder.
  • the preparation can be embedded in the form of a thin continuous layer in the backing material.
  • a very wide variety of substances can be used as backing material for electr-ophotographic materials.
  • Backing materials which are not so conductive electrically as is the photoconductive layer are very useful.
  • metal plates or foils including those which have undergone changes in surface composition by electrical or chemical treatment, papers, fabric fleeces, electrically conductive plastics and foils, electrically conductive ceramic products and so on have proved satisfactory ,as backing materials.
  • Papers or foils which have been vapour coated with metals, supports which have been connected to metal foils, papers or fibre fleeces which have been rendered conductive by an addition of electrolytes or of moisture stabilisers, or such supports as have electron-conductive substances, such as powdered metal, carbon black or graphite embedded in them, are particularly suitable. Also suitable are plastics containing metals or metal compounds, carbon or a large proportion of electrolyte. Non-conductive backings can be provided with a conductive layer of lacquer on their surface. A very wide variety of combinations is therefore possible.
  • auxiliary layer which forms a smooth and closed surface.
  • This auxiliary or intermediate layer can be so devised as, if required, to increase and equ-alise the conductivity of the backing material and to improve the adhesion and anchorage of the electrophotographic layer on the backing.
  • the substances used for the intermediate layer are substances which are dissolved or changed little, if at all, by the preparation which leads to the electrophotographic layer. Organic water-soluble colloids have proved very useful for these purposes.
  • Such substances are, for instance, cellulose ethers, such as methyl celluloses and cellulose glycol acids, including those which have been partly reacted with ethylene oxide or propylene oxide, starch ethers, casein, polyuronides, the salts or amides thereof, ethylene or propylene oxide reaction products, natural colloids, such as Irish moss, starches, including broken-down starches, gelatin, lichenin, agar-agar, tragacanth, hydrate celluloses, .and synthetic resins, such as polyvinyl alcohol, polymethacrylic acid and its acetals, methyl hydantoin resins, maleinate-polyacrylic acid resins or others which contain free carboxyl groups and are Water-soluble in their salt form.
  • cellulose ethers such as methyl celluloses and cellulose glycol acids, including those which have been partly reacted with ethylene oxide or propylene oxide, starch ethers, casein, polyuronides, the salts or amide
  • a further increase in the electrical conductivity of the emulsions can be provided by an addition of soots, metal powders or electrolytes and moisture stabilisers, such as sorbitol, polyglycol ethers, broken-down starches or hygroscopic metal salts.
  • Photoconductive emulsions prepared by the process according to the invention are also of use in the preparation of printing plates such as are used, for instance, for offset printing.
  • the photoconductive layer is produced from compounds having the general Formulae I-III, preferably in their form as self-adhesive photoconductors, possibly in combination with bonding agents or other photoconductors, such as zinc oxide.
  • Particu larly good electrophotographic emulsions for printing can be prepared from the self-adhesive photoconductor type reaction products of those compounds according to Formulae I-III comprising substituents which can react with isocyanates and/or epoxies to form resin-like substances.
  • the solubility of the electrophotographic emulsions can be varied within wide limits by using appropriate compounds which contain isocyanate and/or epoxy groups and by reaction with other substances which are not photoconductors.
  • the preparation forming the photoconductive layer is applied by appropriate applicators, preferably mechanically, to this backing material which has been pretreated to make it stick and/or to make it take up water or which has been provided with hydrophilic intermediate layers, whereafter the photoconductive layer or emulsion is dried.
  • the electrophotographic emulsion should be such that the self-adhesive photoconductors, using compounds having the general Formulae IIII, or the electrophotographically active substances having the general Formulae I-III and also the bonding agent are soluble in conventional solvents or in water, whereas the toner used to produce the image must not be attacked. by the same solvents.
  • the bonding agent is hydrophilic, so that the non-de-emulsified developed printing plate can be used for printing immediately after wetting.
  • the process for preparing printing plates can also be used, of course, to prepare etched engravings, for instance, in the preparation of impression rollers or stereo blocks, and in the preparation of printed circuits.
  • the toner in a form resistant to .acid and in a fused-in state, then serves as masking agent, while the photoconductive layer not required for image production is removed before etching by conventional etching agents, preferably from the metallic support.
  • Example 1 20 g. of phenyl-ot-thienyl-ketone in accordance with Formula 11 are dissolved with slight heating in cc. of ethyl acetate, and there is added to this mixture a solution of 40 g. of a copolymer of vinyl chloride and vinyl acetate (commercial product known as Vinylite VAGH) in 30 cc. of ethyl acetate and 50 cc. of butyl acetate. To produce the photoconductive emulsion, the solution just described is applied in a centrifuge to an electrochemically polished and eloxated aluminium foil. The colourless electrophotographic plate is charged to -7 kv.
  • a copolymer of vinyl chloride and vinyl acetate commercial product known as Vinylite VAGH
  • the positive electrode being formed as a baseplate on which the electrophotographic material is supported.
  • the negative electrode is in the form of thin tungsten wires which are from about 0.02 to 0.1 mm. thick and which are at a distance of from 10 to 15 mm. from the electrophotographic plate and at a distance of 15 mm. from one another. This arrangement is conventionally used to charge the electrophotographic material. If the tungsten wires are made positive in the baseplate negative, the electrophotographic plate is charged positively.
  • the charged electrophotographic material is exposed below an original with a high-pressure mercury vapour lamp for 20 seconds, then developed by means of a tribo electric system comprising a toner and glass balls, the toner being made of plastics, colouring agents and/or soots.
  • a tribo electric system comprising a toner and glass balls, the toner being made of plastics, colouring agents and/or soots.
  • the toner known commercially as the Graph-O- Fax-Toner No. 39/50, of the P. A. Hunt Company, and glass balls are used, a positive original gives a positive image which can be fixed by being heated to C. or by the action of solvent vapours.
  • the electrophotographic material can be used for image transfer in an electric field to other, preferably sheet-like substances, such as paper, plastics foil or the like.
  • Ade- .qua-te sensitivity for working with incandescent light can tising colouring agents to the coating solution, referred to the photoconductor, such as Rhodamin B (Schultz-Earhstofitabellen, Leipzig 1931, No. 864) or brilliant green (Schultz-Farbstotftabellen, Stuttgart 1931, No. 760).
  • Example 2 2 g. of 4-dimethylamino-4'-aminobenzophenone in accordance with Formula 8 are dissolved in l cc. of methylethyl ketone and 10 cc. of dimethyl formamide and added to a solution consisting of 4 g. of a colophonymaleic acid resin, for instance, the commercial product known as Alresat 3l3c, and l g. of ethyl cellulose, for instance, the commercial product known as ethyl cellulose N200, dissolved in 40 cc. of aceto-ethyl.
  • a colophonymaleic acid resin for instance, the commercial product known as Alresat 3l3c
  • l g. of ethyl cellulose for instance, the commercial product known as ethyl cellulose N200, dissolved in 40 cc. of aceto-ethyl.
  • the produced and still unfixed and, for instance, positively charged powder image is covered with a sheet of paper, with a waxed paper or with resin-impregnated paper or with a plastics foil and is so introduced into an electric field produced by a voltage of from 2 to 6 kv. at a spacing of 20 mm. that the negative electrode is associated with the back of the sheet of paper.
  • The, for instance, positively charged toner is therefore transferred to the sheet material in laterally inverted ztorm and can be fixed by heating and/or solvent vapours.
  • Contact copies on a transparent material can be used as intermediate originals for other photocopies, for instance, photoprints, for projection purposes and so on.
  • Example 4 '31 g. of 2-oxy-4-diethylaminobenzophenone-carboxylic acid (2) according to Formula 20, and 0.3 g. of Rhodamin B, are dissolved with heating in 100 cc. of cyclohexanone. There are added to the cooled solution 47 g.
  • reaction product which contains three free isocyanate groups in the molecule and which has been prepared from 1 mol of 1- trimethylol pnopane and 3 mol of toluylene-2,4-diisocyanate and/ or toluylene-Z,6-diisocyanate (commercial product known under the trade mark of Desmodur L), 75% by weight in an ethyl acetate, dissolved in 100 cc. of cyclohexanone.
  • the mixture is condensed at 151 C. with reflux boiling lfOI 20 minutes, the viscosity increasing considerably.
  • the condensation gives the reaction product dissolved in cyclohexanone limited compatibility with acetone.
  • reaction product is mixed with acetone in the proportion of 1, the self-adhesive photoconductor separates out.
  • the reaction should be so controlled that no threeadimensional cross-linking occurs.
  • 25 g. of the reaction solution are mixed with 25 cc. of methyl ethyl ketone and 35 cc. of dioxane and, after filtration, used to prepare the electrophotographic layer, an electrochemically polished aluminium foil being so coated in a centri- (fuge that a layer thickness of about 0.006 mm. dry is produced.
  • the coated plate is dried by ultra-red radiation on the centrifuge, then baked at 130 C. for 5 minutes.
  • a lustrous very strong electrophotognaphic layer which sticks fast mechanically to the backing is produced. It is charged electrostatically at 7 k v. for 3 seconds, exposed below an original with ultra-violet fluorescent tubes for 1 second, then developed using glass balls and a direct toner.
  • a high-contrast electrophotographic image is produced.
  • Another method of producing an image is for the electrophotographic plate just described to be exposed when charged through a microfilm, and for a time of 25 seconds, in an enlarger having a 150 Watt cine-projection lamp, with an aperture ratio of 1:5.6 with a distance of 30 cm. between the lens and the plate.
  • a high-contrast electrophotographic image is yielded after development.
  • the still unfixed electrophotographic recordings can be transferred in an electric field to other substances, preferably in sheet form, as described in Example 1.
  • Example 5 145 g. of 4-N-ethyl-(fi-oxyetbyl)-aminobenzophenone according to Formula 14 are reacted with 300 g. of ethylene glycol diglyoide ether at 170 C. in a nitrogen atmosphere for 30 minutes, whereafter 190 g. of ethylene glycol diglycide ether boiling at from 142-167" C./ 3 torr. are distilled oil in a vacuum produced by an oil pump. The resin which remains as residue is dissolved hot in 500 cc. of cyclohexanone and to this solution there are added 200 g.
  • a modified isocyanate (the commercial product called Desmodur L) in a proportion of 75 by weight in ethyl acetate, and condensation is eifected at C. (usually for 5 minutes) until the solution is still compatible with methyl ethyl ketone and no gelatinisation occurs.
  • 100 cc. of the cooled reaction solution thus prepared are diluted with 200 cc. of methyl ethyl ketone.
  • This solution is applied in a uniform thickness of 0.008 mm. to a highly lustrous aluminium foil.
  • the photoconductive layer formed is dried in an air stream first at C. and then for a short time at C.
  • the electrophotognaphic material formed when charged as set forth in Example 1 to 7 kv. and exposed under a positive original with a highpressure mercury vapour lamp or a pulse discharge tube, yields upon development a high-contrast positive reproduction which can also be used for image transfer.
  • Example 6 77 g. of 4-dimethylamino-4-amino-benzophenone according to Formula 8 are dissolved in 300 cc. of cyclohexanone, 88 g. of a modified triisocy-anate (commercial product called Desmodur L) in a proportion of 75 by weight in ethyl acetate, dissolved in 200 cc. of cyclohexanone, are added and condensing with reflux boiling is effected at from to 152 C. for 30 minutes. To prepare the electrophotographic material, a plastics-impregnated smooth-surfaced glass fibre fleece which has had aluminium vapour coated onto it smooth side is used as backing material. A solution consisting of 50 cc.
  • Example 7 105 g. of 4-[methyl-(fi-hydroxyethyl)-arnino]-cinnam ⁇ al 2' hydroxy 4 dimethylamino-acetophenone corresponding to Formula 26 are dissolved in 300 cc. of cyclohexanone, and 88 g. of a modified triisocyanate (commercial product called Desmodur L), in a proportion of 75% by weight in ethyl acetate, are added and reacted at 150 C. for 20 minutes. 100 cc. of the reaction solution are mixed with 50 cc. of methyl ethyl ketone and with 50 cc.
  • Desmodur L a modified triisocyanate
  • the electrophotographic material is charged up to 6 kv. and exposed under a positive original with a high-pressure mercury vapour lamp or an arc lamp or ultra-violet fluorescent tubes.
  • a toner having a particle size of from to 50 1.1. and glass balls a high-contrast positive image of the original is produced which can be fixed by heating and/ or solvent vapours.
  • the unfixed image on the electrophotographic plate is brought into intimate contact with sheet material and so introduced into an electric field that, for instance, the negative electrode is disposed behind the sheet material. If the electric field is strong enough, for instance, of 6 kv./ 20 mm., printing is elfected by the field strength alone. By intermediate changes of a field of differing field strength and direction, varying quantities of toner can be. transferred and a number of copies can be prepared from one image on the electrophotographic plate. The transfer image is fixed like the electrophotographic plate.
  • the backing material is a copper foil which has a smooth front but a spongy back and which is connected on the back to a resilient high-melting plastic or to rubber.
  • the dissolved self-adhesive photoconductor is applied to the front of this backing material and dried in an air stream at 100 C. to remove the solvents, whereafter the front is given a brief radiant heat treatment at 120 C.
  • This solution of self-adhesive photoconductor is applied by applicator comprising dispensing rollers onto an aluminium-vapour-coated cellulose paper having a density of g./m. dried in a Warm air stream, then given brief afterheating at C.
  • the self-adhesive photoconductor is very photosensitive.
  • the substance When charged up in a coronary discharge arrangement to -7 kv., then exposed below a positive original with ultra-violet cold light tubes for 3 seconds, the substance, after development with glass powder and a direct toner, provides a high-contrast positive image which is fixed by heating or by solvent vapours.
  • liquid developers comprising a dispersion of dye particles with an addition of soluble or dispsersed plastics in a liquid medium.
  • development can be effected if the liquid phase of the developer is such that the electrophotographic emulsion is not dissolved.
  • the photoconductive emulsions prepared from self-adhesive photoconductors are of the kind which still contain reactable isocyanate and/or epoxy groups and are given three-dimensional cross-linking during the production of the electrophotographic emulsion.
  • small quantities of polyamines, polycarboxylic acids or polyalcohols are added to the preparation which will subsequently lead to the electrophotographic layer, and cross-linking is effected during drying by the use of heat.
  • Example 10 15 g. of a chlorinated diphenyl resin, for instance, the commercial product called Clophenharz W, and 3 g. of a broken-down natural rubber, for instance, the commercial product known as Cyclosit, are heated to 150 C. to produce a homogeneous melt. 5 g. of tetramethyl-4,4'- diaminobenzophenone in accordance with formula 1 are dissolved in the melt, whereafter the same is used, at a temperature of from to C., to coat heat-stable backing materials for electrophotography, for instance, by the melt being applied to aluminium sheet which has been heated to 140 C.
  • a chlorinated diphenyl resin for instance, the commercial product called Clophenharz W
  • 3 g. of a broken-down natural rubber for instance, the commercial product known as Cyclosit
  • Emulsion thicknesses of from 0.005 to 0.01 mm. are very useful to provide short exposure times and a substantially colourless emulsion.
  • the electrophotographic material is charged up to 7 kv. and exposed below a positive original with ultra-violet fluorescent tubes for 15 seconds. After development as set forth in Example 1, a high-contrast positive electrophotographic image results which is fixed by heating or by solvent vapours or which can be used for transfer to other materials in an electric field.
  • High sensitivity to incandescent light can be provided by an addition of 0.2 g. of Rose bengale (Schultz- Farbstoiftabellen 1931, No. 889) 0.05 g. of Pinaflavol (Schultz-Farbstoiftabellen 1931, No. 925 and 0.05 g. of Pinacyanol (Schultz-Farbstofitabellen 1931, No. 924).
  • the electrophotographic layer is applied from the melt to the backing material by means of pressing tools which ensure a thin and uniform thickness of the emulsion.
  • the material is ready for use immediately after cooling.
  • Example 11 dissolved in 20 cc. of methyl ethyl ketone, are added.
  • a 60 g./m. cellulose paper is coated with a preparation to inhibit penetration of the electrophotographic layer and with a conductivity-promoting protective layer.
  • the latter layer is prepared, for instance, by application of a solution consisting of:
  • the preparation leading to the photoconductive layer is applied to the backing material which has been thus prepared, and is dried in a stream of warm air at 120 C.
  • the electrophotographic material can be used for image production as set forth in Example 1. When the material is charged negatively, placed under a positive original and exposed with a high-pressure mercury vapour lamp and developed, a positive image is provided.
  • the preparation just described for the production of the electrophotographic emulsion can also be used in the preparation of printing forms. To this end, it is applied to a backing material which has a hydrophilic surface, for instance, in the form of a colloidal layer, or which is in the form of an electrically or chemically pretreated metal foil, and the whole is dried in a warm air stream.
  • the electrophotographic material is ready for use after drying and can be cleaned by being washed with Water and/or detergents.
  • the electrophotographic plate is briefly charged at 7 kv., then placed below a positive original and irradiated with short-wave light either by the direct contact method or with the interposition of a microfilm in the projection method.
  • a positive image is provided after development with a toner which is insoluble in alcohol and is suitable more particularly to receive printing ink, and with glass balls.
  • the toner is melted into the photoconductive layer.
  • the electrophotographic plate is converted into a printing form, that area of the photoconductive emulsion which has not been used for the image being removed.
  • the form after being wiped over with 30% phosphoric acid and possibly being given a further short melting-in treatment, is inked on an offset printing press with a simultaneous supply of water and printing ink. The form gives a large run with exact reproduction of the print.
  • Example 12 87.5 g. of a modified triisocyanate, formed by reacting 3 mol of 2,4-toluylene diisocyanate and 1 mol trimethylolpropane containing three free isocyanate groups (for instance, the commercial product called Desmodur L), 75% by weight in ethylacetate, 28 g. of n-dodecanol and 57.5 g. of 4 [methyl (/3-hydroxyethyl)-amino]-cinnamal-4-diphenyl-acetophenone in accordance with the Formula 23, are dissolved in 200 cc. of cyclohexanone and reacted at 140 C.
  • a modified triisocyanate formed by reacting 3 mol of 2,4-toluylene diisocyanate and 1 mol trimethylolpropane containing three free isocyanate groups (for instance, the commercial product called Desmodur L), 75% by weight in ethylacetate, 28 g. of n-d
  • reaction product is diluted with 400 cc. of ethyl amyl ketone, and 1 g. of Rhodamin 3 B (No. 867), 0.3 g. of Orthochrom T (No. 923), and 0.3 g. of naphthacyanol (No. 926) are added, the numbers which follow the sensitisers referring to the SchultZ-Farbstolftabellen, vol. 1, 1931.
  • the solution just described is so applied mechanically to a paper-lined aluminium foil, and so dried in a warm air stream at 125 C., that the thickness of the emulsion is from 0.005-002 mm. A firmly adhering highly photosensitive photoconductive layer is produced.
  • the aluminium foil of the electrophotographic material is connected to the positive side of the charging device and charged to a negative corona of kv.
  • the material is exposed, through a film bearing a positive image, in an enlarger comprising a 250-watt incandescent lamp at an steps of the process.
  • the powder image can be fixed by known steps, such as by being heated to 120 C.
  • the photoconductive emulsion is charged with a positive corona of 10 kv., exposed through a negative original and developed with a reversal toner, for instance, the commercial product known as Xerox-Toner SCl3, and glass balls, a positive image of the negative original is provided.
  • Example I 10 g. of tetramethyl-4,4-diaminothiobenzophenone in accordance with Formula 2, and 0.3 g. of Rhodamin 3 B, corresponding to the Schultz-Farbstofitabellen 1931, No. 867, are dissolved in 40 g. of a chlorinated diphenyl resin, for instance, the commercial product known as Clophen Harz W, which has been heated to 120 C. This melt is used in the preparation of electrophotographic material in the manner set forth in Example 10.
  • a chlorinated diphenyl resin for instance, the commercial product known as Clophen Harz W, which has been heated to 120 C. This melt is used in the preparation of electrophotographic material in the manner set forth in Example 10.
  • Example 14 30 g. of 4,4'-bis-dimethylamino-di-benzylidene acetone in accordance with Formula 27, and 87.5 g. of the reaction product prepared from 3 mol of toluylene-2,4 (or 2,6)-diisocyanate and 1 mol of trimethylolpropane (for instance, the commercial product known as Desmodur L), by weight in ethyl acetate, are dissolved hot in 150 cc. of cyclohexanone and 300 cc. of 'ethylamyl ketone. A solution of 20 g. of hexane-diol-l,6 in cc.
  • the applied and still solvent-containing photoconductive emulsion or layer is dried in a warm air stream and after-heated at 140 C. for a further 5 minutes.
  • a firmly adhering photoconductive layer of a deep orange-reddish colour is produced which is very sensitive to incandescent light and to longwave ultra-violet light.
  • the electrophotographic material is charged to -6 kv. for a short time, then exposed for 5 seconds through a microfilm in an enlarger having a 250 watt cineprojection lamp, through a lens having an aperture ratio of 1:4.5, with a distance of 30 cm.
  • the picture thus prepared can be used for image transfer in an electric field or by pressing, for instance, on paper or plastics foils. Fixing is by heating and/0r solvent vapours.
  • Example 15 2 g. of 4,4'-dimethoxy-thiobenzophenone in accordance with Formula 6, 4 g. of a ketone or aldehyde resin, for instance, the synthetic resin known commercially as AP, and l g. of 65% collodion wool, wetted with ethanol, are dissolved in 4 cc. of ethanol, 60 cc. of acetone and 20 cc. of butyl acetate. The' solution is used to coat a 0.3 mm. thick aluminium foil in a centrifuge, the coating being uniform, whereafter drying is effected in an air stream at C.
  • the electrophotographic material has a high metallic lustre and a slight blue tinge. When the material is charged to 7 kv. and exposed with a highpressure mercury vapour lamp below a positive original, a high-contrast positive electrophotographic image of high storage capacity is produced.
  • Example 16 g. of 2-oxy-4-diethylamino-benzophenone-carboxylic acid (2)-methyl ester in accordance with Formula 21, 0.2 g. of Rhodamin B (Schultz-Forbstofftabellen No. 864), and 17.5 g. of a modified isocyanate having three reactable isocyanate groups in the molecule, for instance, the commercial product known as Desmodur L, are dissolved in 45 cc. of cyclohexanone and condensed with reflux boiling for 30 minutes. The solution is cooled to room temperature, then 5.6 g. of di-(2-ethylh'exyl)-amine dissolved in cc. of cyclohexanone are added and the mixture is reacted at 100 C. for 10 minutes.
  • Rhodamin B Schotz-Forbstofftabellen No. 864
  • the photoconductive emulsion produced from this selfadhesive photoconductor is readily soluble in lower aliphatic alcohols and is very sensitive to incandescent light. It is very useful for producing electrophotographic material for use in printing forms, more particularly for offset printing.
  • the solution of self-adhesive photoconductor preferably in a very dilute condition, is applied to a print support and dried.
  • print supports there are suitable papers which have'been pretreated with a colloidal emulsion, aluminium foils which- Example 17 43.75 g. of triisocyanate modified in accordance with Example 12, 75 by weight in ethylacetate, and 32 g. of 2,4-di-hydroxy benzophenone are dissolved in 100 cc.
  • 1 part by volume of the solution of self-adhesive photoconductor is diluted with 2 parts by volume of methyl ethyl ketone and so applied to a bright eloxated aluminium plate, to produce the photoconductive emulsion, and dried, that the emulsion thickness is 0.01 mm.
  • the hard substantially colourless photoconductive emulsion sticks satisfactorily to the backing material and has a high storage capacity for the electric charge. If the emulsion is charged with a negative corona to 10 kv.
  • R is selected from the group consisting of an aliphatic residue of 1-l2 carbon atoms, phenyl, naphthyl, diphenyl, polar substituted phenyl, naphthyl, and diphenyl,
  • polar substituents are selected from the group consisting of OH, SH, -NH NHCHg, NHC H Cl, -CN or COOH;
  • Ar and Ar are each selected from the group consisting of mononuclear rings having aromatic properties, two mononuclear rings having aromatic properties connected to one another by a single carbon atom, and two ortho condensed mononuclear rings having aromatic properties, and wherein n is any whole number selected from 1, 2 and 3 and n is whole numbers from Zero to 3.
  • R is selected from the group consisting of an aliphatic residue of 112carbon atoms, phenyl, naphthyl, di-v phenyl, polar substituted phenyl, naphthyl, and diphenyl,
  • polar substituents are selected from the group consisting of OH, SH, -NH NHCH NHC H Cl, CN or COOH;
  • Ar and Ar are each selected from the group consisting of mononuclear rings having aromatic properties, two mononuclear rings having aromatic properties connected to one another by a single carbon atom, and two ortho condensed mononuclear rings having aromatic properties, and wherein n is any whole number selected from the group consisting of 1, 2 and 3 and n is any integer from zero to 3.
  • An electrophotographic material comprising a carrier and an electrophotographic layer thereon containing.
  • a low molecular weight nonpolymeric compound selected from the group consisting of ketones and thioketones having the formula t it.
  • Z is selected from the group consisting of O and S.
  • An electrophotographic material comprising a carrier and an electrophotographic layer thereon containing a mixture of the reaction product of claim 5 and zinc oxide.
  • An electrophotographic material comprising a carrier and an electrophotographic layer thereon containing a mixture of the reaction product of claim 6 and zinc oxide.
  • An electrophotographic material comprising a carrier and an electrophotographic layer thereon containing a low molecular weight nonpolymeric compound selected from the group consisting of ketones and thioketones having the formula wherein X and X are each selected from the group consisting of NHR, NR OR, SR, COOR, CONHR, CONR -SO NHR and SO NR and wherein R is selected from the group consisting of phenyl, naphthyl, and diphenyl, each substituted by polar substituents selected from the group consisting of OH, SH, NH NHCH -NHC H COOH, CN, and Cl, and wherein Z is selected from the group consisting of O and S; and wherein n is any whole number selected from the group consisting of 1, 2 and 3 and n is any integer from zero to 3.
  • An electrophotographic material comprising a carrier and an electrophotographic layer thereon containing a material selected from the group consisting of:

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Cited By (12)

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US3352670A (en) * 1964-02-14 1967-11-14 Minnesota Mining & Mfg Supersensitizers for optically sensitized photoconductive layers
US3387973A (en) * 1961-12-29 1968-06-11 Eastman Kodak Co Photoconductive substances having triphenylamine moieties for electrophotography
US3493369A (en) * 1964-04-03 1970-02-03 Appleton Coated Paper Co Low electrical resistance varnish coatings on an insulating base
US3526501A (en) * 1967-02-03 1970-09-01 Eastman Kodak Co 4-diarylamino-substituted chalcone containing photoconductive compositions for use in electrophotography
US3533787A (en) * 1967-07-31 1970-10-13 Eastman Kodak Co Photoconductive elements containing polymeric binders of nuclear substituted vinyl haloarylates
US3652269A (en) * 1968-08-27 1972-03-28 Eastman Kodak Co Photoconductive elements containing halogenated polyethylene binders
US3873312A (en) * 1973-05-04 1975-03-25 Eastman Kodak Co Photoconductive composition and elements containing a styryl amino group containing photoconductor
US3873311A (en) * 1973-05-04 1975-03-25 Eastman Kodak Co Aggregate photoconductive compositions and elements containing a styryl amino group containing photoconductor
US3994724A (en) * 1969-07-23 1976-11-30 Scott Paper Company Photoconductor elements containing substituted aniline photoconductor compounds
US4287336A (en) * 1978-09-22 1981-09-01 Ciba-Geigy Corporation Chromogenic propenylenesulfone compounds
US5486441A (en) * 1993-04-28 1996-01-23 Takasago International Corporation Electrophotographic photoreceptor containing 1,4-bis(4,4-diphenyl-1,3-butadienyl)benzene derivative
JP2000319628A (ja) * 1999-04-20 2000-11-21 Basf Ag 光安定性ｕｖフィルターとしてのアミノ置換されたヒドロキシベンゾフェノンの使用、該化合物を含有する光保護剤及びアミノ置換されたヒドロキシベンゾフェノン

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DE2734289C2 (de) * 1977-07-29 1982-06-09 Hoechst Ag, 6000 Frankfurt Photoleiterband
JP2817822B2 (ja) * 1992-05-14 1998-10-30 富士電機株式会社 電子写真用感光体

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US2710274A (en) * 1952-03-26 1955-06-07 Kuehl Georg Walter Multi-layer glass sheet
DE1060713B (de) * 1956-11-21 1959-07-02 Kalle & Co Ag Material fuer die elektrophotographische Reproduktion
DE1105713B (de) * 1959-04-08 1961-04-27 Kalle Ag Material fuer elektrophotographische Reproduktion
US3025160A (en) * 1957-06-08 1962-03-13 Agfa Ag Electrostatic printing
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US2710274A (en) * 1952-03-26 1955-06-07 Kuehl Georg Walter Multi-layer glass sheet
BE562336A (fr) * 1956-11-14
DE1060259B (de) * 1956-11-14 1959-06-25 Agfa Ag Verfahren zur Herstellung von photoleitfaehigen Schichten fuer elektrophotographische Verfahren
DE1060713B (de) * 1956-11-21 1959-07-02 Kalle & Co Ag Material fuer die elektrophotographische Reproduktion
US3025160A (en) * 1957-06-08 1962-03-13 Agfa Ag Electrostatic printing
US3155503A (en) * 1959-02-26 1964-11-03 Gevaert Photo Prod Nv Electrophotographic material
DE1105713B (de) * 1959-04-08 1961-04-27 Kalle Ag Material fuer elektrophotographische Reproduktion

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3387973A (en) * 1961-12-29 1968-06-11 Eastman Kodak Co Photoconductive substances having triphenylamine moieties for electrophotography
US3352670A (en) * 1964-02-14 1967-11-14 Minnesota Mining & Mfg Supersensitizers for optically sensitized photoconductive layers
US3493369A (en) * 1964-04-03 1970-02-03 Appleton Coated Paper Co Low electrical resistance varnish coatings on an insulating base
US3526501A (en) * 1967-02-03 1970-09-01 Eastman Kodak Co 4-diarylamino-substituted chalcone containing photoconductive compositions for use in electrophotography
US3533787A (en) * 1967-07-31 1970-10-13 Eastman Kodak Co Photoconductive elements containing polymeric binders of nuclear substituted vinyl haloarylates
US3652269A (en) * 1968-08-27 1972-03-28 Eastman Kodak Co Photoconductive elements containing halogenated polyethylene binders
US3994724A (en) * 1969-07-23 1976-11-30 Scott Paper Company Photoconductor elements containing substituted aniline photoconductor compounds
US3873312A (en) * 1973-05-04 1975-03-25 Eastman Kodak Co Photoconductive composition and elements containing a styryl amino group containing photoconductor
US3873311A (en) * 1973-05-04 1975-03-25 Eastman Kodak Co Aggregate photoconductive compositions and elements containing a styryl amino group containing photoconductor
US4287336A (en) * 1978-09-22 1981-09-01 Ciba-Geigy Corporation Chromogenic propenylenesulfone compounds
US5486441A (en) * 1993-04-28 1996-01-23 Takasago International Corporation Electrophotographic photoreceptor containing 1,4-bis(4,4-diphenyl-1,3-butadienyl)benzene derivative
JP2000319628A (ja) * 1999-04-20 2000-11-21 Basf Ag 光安定性ｕｖフィルターとしてのアミノ置換されたヒドロキシベンゾフェノンの使用、該化合物を含有する光保護剤及びアミノ置換されたヒドロキシベンゾフェノン

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