EP0161648B2 - Matériau d'enregistrement électrophotographique - Google Patents

Matériau d'enregistrement électrophotographique Download PDF

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Publication number
EP0161648B2
EP0161648B2 EP85105785A EP85105785A EP0161648B2 EP 0161648 B2 EP0161648 B2 EP 0161648B2 EP 85105785 A EP85105785 A EP 85105785A EP 85105785 A EP85105785 A EP 85105785A EP 0161648 B2 EP0161648 B2 EP 0161648B2
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EP
European Patent Office
Prior art keywords
layer
recording material
organic
weight
type conducting
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EP85105785A
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German (de)
English (en)
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EP0161648B1 (fr
EP0161648A1 (fr
Inventor
Jürgen Dr. Dipl.-Chem. Lingnau
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Hoechst AG
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Hoechst AG
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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
    • G03G5/06—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
    • G03G5/0622—Heterocyclic compounds
    • G03G5/0644—Heterocyclic compounds containing two or more hetero rings
    • G03G5/0646—Heterocyclic compounds containing two or more hetero rings in the same ring system
    • G03G5/0657—Heterocyclic compounds containing two or more hetero rings in the same ring system containing seven relevant rings

Definitions

  • the invention relates to an electrophotographic recording material consisting of an electrically conductive layer support, optionally an insulating barrier layer and a photoconductive layer, the photoconductive layer containing at least one organic, n-conductive pigment, at least one electronically inert binder and photoconductor containing carbonyl groups.
  • the recording material is suitable for repeated or single use in copiers, as a printing form or as a printed circuit.
  • Color pigments that generate charge carriers include perinones (DE-OS 2 239 923, corresponding to GB-PS 1 416 603, DE-OS 2 108 958, corresponding to US-PS 3 879 200), perylenetetracarboxylic acid diimides (DE-OS 2 237 539, correspondingly US-PS 3 871 882, DE-OS 2 108 992, corresponding to US-PS 3 904 407) and condensed quinones (DE-OS 2 237 678, corresponding to US-PS 4 315 981, DE-OS 2 108 935, corresponding to US -PS 3 877 935) is used.
  • perinones DE-OS 2 239 923, corresponding to GB-PS 1 416 603, DE-OS 2 108 958, corresponding to US-PS 3 879 200
  • perylenetetracarboxylic acid diimides DE-OS 237 539, correspondingly US-PS 3 871 882, DE-OS 2 108 992,
  • a double-layer structure with a lower layer which generates charge carriers and has a low layer thickness with a high color pigment concentration and a relatively thick charge transport layer composed of inert binder and organic p-conducting photoconductor.
  • layer arrangements are specified in which the sensitizing color pigment and the p-type photoconductor are applied together in one layer on the electrically conductive layer support.
  • the concentration of the color pigment is only 0.1 to 5% by volume of the photoactive layer.
  • organic p-conducting photoconductor - aromatic or heterocyclic compounds - must be present in the layer in a concentration of at least 25 percent by volume in order to achieve sensibilities which can be used in practice.
  • Electronically inert polymers such as polystyrene, polyacrylate, cellulose nitrate, polyvinyl acetate, chlorinated rubber and the like are described as binders. v. a.
  • Electrophotographic layers consist of a photoconductive pigment and an electronically inert binder.
  • Zinc oxide for example in US Pat. No. 3,121,006, cadmium sulfide, for example in US Pat. No. 3,238,150, and a number of other inorganic compounds are described as photoconductive pigments.
  • the charge transport in these layers is achieved by a high concentration of the photoconductive pigment. With such a layer structure, a pigment concentration of over 50 percent by volume is required in order to enable particle contact of the photoconductive particles.
  • DE-OS 3 227 475 corresponding to US Pat. No.
  • part of the inorganic pigment can also be replaced by organic, photoconductive pigments, the pigments such as CI Pigment Red 168 and CI Pigment Orange 43 having proven themselves equally well Represent derivatives of naphthalene tetracarboxylic acid diimides.
  • the total amount of photoconductor in the layer required for practical use is between 20 and 80 percent by weight.
  • binders - because of their use for electrophotographic offset printing plates - alkaline stripping or dispersing polymers are claimed.
  • monolayers for positive charging can also be produced from Cu-phthalocyanine in s-form (JP-AS 0/38543).
  • the resulting ⁇ complex shows good sensitivity with poly-N-vinylcarbazole as a binder / p-type photoconductor (50:50).
  • photoconductors with a double layer arrangement are used.
  • this arrangement has the disadvantage that its manufacture in two coatings Application steps are carried out, which is more complex than the production of a monolayer material.
  • a disadvantage of double-layer arrangements is that they have an unfavorable residual charge behavior.
  • monolayers based on zinc oxide can be used for cyclic image reproduction, which have low residual charge potentials. Because of the large proportion of zinc oxide, however, layers of this type show a relatively low mechanical stability and a relatively poor charge acceptance.
  • Double-layer photoconductors with a roughly equal pre-coat of pigment and binder and top coat of p-conductive photoconductor and binder according to German patent application, file number P 33 29 442.9, can be used for the electrophotographic production of offset printing plates, but are significantly less sensitive than the first and from Manufacturing costs also unfavorable, monolayer photoconductor with dissolved sensitizing dyes (DE-OS 2 526 720, corresponding to US Pat.
  • No. 4,063,948 show similar sensitivities, but are, in contrast to the pigment layers, sensitive to pre-exposure, i.e. H. their charge acceptance is significantly impaired by prior exposure.
  • Monolayers with low concentrations of sensitizing pigment show poorer image reproduction in addition to significantly lower photosensitivity than the double layers.
  • all the layer arrangements described have in common undesired, relatively large residual potentials after the end of the exposure, which increase drastically with increasing layer thickness and lead to difficulties in making the latent charge image visible.
  • Another object of the invention was to make the recording material applicable for the production of printing forms and printed circuits (printed circuit boards) by using suitable binders and low concentration of the p-type photoconductor.
  • the photoconductive layer is the organic n-conductive pigment selected from a compound of the class of the trans-perinones, the perylene-tetracarboxylic acid diimides or the condensed one Quinones, in a concentration between 10 and 50 percent by weight, based on the layer weight, and as photoconductor exclusively organic p-type photoconductor in a concentration up to 20 percent by weight, based on the layer weight.
  • the recording material in the photoconductive layer contains the organic n-type pigment in a concentration between 15 and 30 percent by weight and the organic p-type photoconductor in a concentration of 2 to 8 percent by weight, based on the layer weight.
  • concentrations of 20-30 percent by weight for the organic, n-type pigment and of 2-5 percent by weight for the organic, p-type photoconductor have proven successful.
  • the organic p-type photoconductor can be present in the layer in a homogeneously distributed form, but it can also be present in a gradient distribution by diffusion into the layer or else in a step-like distribution by double-layer arrangement.
  • Pigments of the following general formulas 1 to IV can be used as the n-conducting pigment.
  • pigments are referred to in a number of publications as photoconductive, which means, however, that photoconductivity is regularly understood in cooperation with other photoconductors.
  • the color pigments play the role of the sensitizer, which forms charge carriers in cooperation with the p-type photoconductor. In accordance with this role, pigments are used either in very thin layers that generate charge carriers or, in the case of homogeneous distribution, in relatively low concentrations.
  • UP-PS 3 879 200 and US-PS 3 904 407 can only achieve good electrophotographic properties in these cases.
  • a star becomes part of the photoconductive layers according to the invention Ker trap effect observed in the initial phase of the discharge, which leads to an S-shaped discharge profile instead of the approximately exponential discharge characteristic which is otherwise exponential in organic photoconductor systems (e.g. DE-PS 2 237 539).
  • This S-shaped discharge characteristic provides particularly high voltage contrasts in the range of medium exposure energies and can therefore be used to produce charge and toner images of particularly hard gradation and particularly high resolution.
  • the utilization of the n-conductivity of pigments used according to the invention requires a minimum pigment concentration, which is to be set at about 10 percent by weight, based on the layer weight. Excessively high pigment concentrations lead to a deterioration in the charge acceptance, so that approximately 50% by weight of pigment is to be regarded as the upper limit. Pigment concentrations between 15 and 30 percent by weight have proven particularly successful. At these pigment concentrations, especially in the higher range, when the alkali-soluble binders according to the invention are used, the decoating ability of the photoconductive layer for use in electrophotographic imageable printing forms and the like also remains. Like. Guaranteed.
  • n-type pigments When using n-type pigments according to the invention, an increase in sensitivity was found if p-type photoconductors were added to the layer to a small extent.
  • Compounds which are usually used in electrophotographic layers are suitable as such. Examples are oxdiazoles, oxazoles, aromatic amines, triphenylmethanes, hydrazones, but also polymeric compounds, such as polyvinyl carbazole, as described, for example, in German patents 10 58 836, 10 60 260, 11 20 875, 11 97 325 and 10 68 115 and 11 11 935 emerge.
  • the concentration of the p-type photoconductor should not exceed 20 percent by weight, based on the layer weight. Concentrations between 2 and 8 percent by weight have proven particularly useful.
  • the p-conductivity of the photoconductor only contributes to the generation of charge carriers and to the removal of the positive charge carriers in the upper region of the photoconductive layer.
  • the addition of p-type photoconductor can therefore also be restricted to these upper zones, which has proven to be advantageous particularly in the case of thicker layers in an arrangement in the upper region.
  • a targeted addition of the p-type photoconductor into the upper zones can either be achieved by a double-layer structure or by post-treatment of the finished layer which does not contain the p-type photoconductor with corresponding solutions of the photoconductor which are applied without a binder.
  • Such electronically inert binders containing carbonyl groups are used which are soluble or dispersible in aqueous alkaline solution.
  • Copolymers of methacrylic acid esters and methacrylic acid, optionally with other monomers such as acrylic acid, styrene, are preferably used for this purpose.
  • binders whose glass transition temperature is significantly lower have proven suitable for use as an electrophotographic dry resist. Only in such a case can a complete transfer of the photoconductive layer be achieved with a lamination layer. Copolymers of the monomers acrylic acid, longer-chain acrylic or methacrylic acid esters, optionally in combination with other monomers such as methacrylic acid, styrene, have proven particularly useful as binders. There are no restrictions on the glass transition temperature of the binder for use as a liquid resist.
  • the thickness of the photoconductive layer depends primarily on the intended use. In order to ensure sufficient charge acceptance, it should not be less than about 3 g / m 2 . When used as a liquid resist or for the production of electrophotographic printing plates, it is expediently between approximately 5 and 30 g / m 2 , for photoconductor tapes or drums in copiers between approximately 10 and 20 g / m 2 and for laminatable material between approximately 20 and 50 g / m 2 . A sharp increase in the residual potential with the layer weight cannot be observed.
  • the coating with the photoconductive layer is carried out in the usual way from the solution, for example by doctor or spray application.
  • the application is made with a flow machine.
  • the layer is dried, for example, in drying channels.
  • the recording material according to the invention can also be produced for the application of the dry resists by applying the photoconductive layer to the electrically conductive layer support by lamination under heat and pressure from an intermediate support, for example a polyethylene terephthalate film. Because of the relatively low proportion of p-type photoconductor, the recording material according to the invention can be used in the form of a layer support and a coating solution as a liquid resist. In this case, it is up to the user to apply the coating using a wipe-on process.
  • Such a small layer thickness serves as an insulating barrier layer.
  • polymers which bring about better adhesion of the photoconductive layer to the carrier material, for example UV or thermally curable systems.
  • these can also be insulating metal oxide layers, for example aluminum oxide, which bring about hydrophilization of the carrier surface.
  • the layer thickness of the insulating barrier layer should not exceed 4 g / m 2 .
  • Metals can be used as the electrically conductive layer supports, but plastic supports metallized by vapor deposition or lamination can also be used. In addition, plastics with a conductive coating made of polymeric binders and conductive materials such as metal powders or graphite dust can be used.
  • a conductive coating made of polymeric binders and conductive materials such as metal powders or graphite dust can be used.
  • plates made of roughened and anodized aluminum are preferably used as layer supports.
  • the preferred support is copper or has a copper surface such as copper clad polyamide film.
  • the layer contains substances which are added to the coating solution as conventional additives, which may be up to 5% by weight in the photoconductive layer. They improve the surface structure and the flexibility of the layer. These can be, for example, plasticizers, such as triphenyl phosphate, or leveling agents, such as silicone oils.
  • the invention is illustrated by the following examples and comparative examples, without being limited thereto.
  • the layer obtained after drying is dark red and matt.
  • Hostapermorange GR Pigment Orange 43, CI 71 105, formula were introduced into 200 g of tetrahydrofuran in a solution of 10 g of polybutyl methacrylate ( R Plexigum P 676, Röhm GmbH) and dispersed by milling in a ball mill for 2 hours
  • Addition of 3 g of 2,5-bis- (4-diethylaminophenyl) -oxdiazole-1,3,4 and 32 g of polymethyl methacrylate ( R Plexigum M 345) in 340 g of tetrahydrofuran made the layer with a layer weight of 6 g / m 2 Aluminum-coated polyethylene terephthalate film applied and dried.
  • Example 2 The procedure was as in Example 2, with the difference that, instead of the oxdiazole mentioned, 1,5-diphenyl-3-p-methoxyphenylpyrazoline according to DE-AS 10 60 714, corresponding to US Pat. No. 3, 180, 729, and instead a terpolymer of styrene, hexyl methacrylate and methacrylic acid in a molar ratio of 10:60:30 was used for the polybutyl methacrylate and the polymethyl methacrylate.
  • the coating was carried out on roughened and anodized aluminum support material in a layer thickness of about 6 g / m 2 .
  • the layer was treated with a dry developer after charging and imagewise exposure. After fixing, it was possible to remove the base coat with a commercially available decoating solution.
  • the resulting offset printing plate showed a high resolution and, in a printing test, gave good printing qualities up to a print run of well over 100,000.
  • Example 3 The procedure was as in Example 3, with the difference that instead of pyrazoline, 4-methoxybenzaldehyde diphenylhydrazone (DE-OS 32 46 036) and instead of Hostapermorange GR as dye N, N '- (3-methoxypropyi) peryienetetracarboxylic acid 3,4,9,10-diimide ( R Paliogen-black, BASF AG) was used.
  • Example 2 The procedure was as in Example 1, with the difference that the layer was applied to the layer support with a layer thickness of 20 g / m 2 .
  • Example 3 The procedure was as in Example 3, with the difference that copper-clad polyimide film was used instead of the anodized aluminum support.
  • the coated film obtained in this way could be stripped perfectly after the imaging and fixing of the toner image at the areas not covered by toner.
  • High-quality, flexible printed circuit boards were obtained by etching away the metal areas underneath.
  • a layer of 25% by weight of Hostapermorange GR and 75% by weight of the terpolymer from Example 3 with a layer weight of 3 g / m 2 was first applied to anodized aluminum supports.
  • a top coat of 25% by weight of Hostapermorange GR, 20% by weight of 2,5-bis- (4-diethylaminophenyl) -oxdiazole-1,3,4 and 55% by weight of the terpolymer was coated on this underlayer with a layer weight of 3 g / m 2 applied.
  • a primer (undercoat) of 6 g / m 2 was applied to an anodized aluminum support.
  • the dried layer was then treated with a solution of 5% by weight of 2,5-bis (4-diethylaminophenyl) oxdiazole-1,3,4 in tetrahydrofuran and dried again.
  • Analogous results can be achieved by treating the still wet primer with an oxdiazole solution (wet-on-wet coating).
  • Example 2 The procedure was as in Example 2, with the difference that a polyester ( R Dynapol L206, Dynamit Nobel AG) was used instead of the methacrylates.
  • the material thus obtained had high flexibility with good adhesion of the layer to the support. Even when used in cyclic copiers, it showed no change in the electrophotographic properties with the number of charging and exposure cycles.
  • Example 2 The procedure was as in Example 2, with the difference that a polyurethane ( R Desmolac 2100, Bayer AG) was used instead of the terpolymer.
  • a polyurethane R Desmolac 2100, Bayer AG
  • Example 2 The procedure was as in Example 2, with the difference that polyvinylcarbazole ( R Luvikan. BASF AG) was used as the photoconductor and N, N'-dimethyiperyiene-3,4,9,10-tetracarboxylic acid diimide was used as the pigment.
  • polyvinylcarbazole R Luvikan. BASF AG
  • N, N'-dimethyiperyiene-3,4,9,10-tetracarboxylic acid diimide was used as the pigment.
  • Example 2 The procedure was as in Example 2, with the difference that Hostapermscharlach GO (Formula IV, C.I. 59300) was used as pigment.
  • Hostapermscharlach GO Form IV, C.I. 59300
  • a charge transport layer from the following solution was applied to this charge-generating layer, dry layer weight likewise 3 g / m 2 : 50 g of a copolymer of styrene and maleic anhydride and 50 g of 2,5-bis (4-diethylamino-phenyl) oxdiazole -1.3.4 were dissolved in 700 g of tetrahydrofuran and 250 g of butyl acetate with the addition of 0.1 g of silicone oil.
  • a monolayer with a layer weight of 6 g / m 2 from the following dispersion was applied to a roughened and anodized aluminum printing plate support: 6.25 g of Hostapermorange GR and 4.2 g of the terpolymer from Example 3 were in 50 g of tetrahydrofuran by milling in a ball mill for 2 hours dispersed or dissolved and then added to a solution of 50 g of 2,5-bis (4-diethylaminophenyl) -oxdiazole-1,3,4, 40 g of the terpolymer from Example 3 and 0.1 g of silicone oil in 850 g of tetrahydrofuran .
  • This example corresponds to a sensitive monolayer formulation described in U.S. Patent 3,879,200.
  • Example 3 The procedure was as in Example 3, with the difference that instead of the methacrylate terpolymer, a likewise aqueous-alkaline decoatable sulfonyl urethane (prepared according to DE-OS 32 10 577, Example 1) was used.
  • Example 2 The procedure was as in Example 2, with the difference. that cellulose nitrate with a degree of nitration of 12.2% was used instead of the methacrylates.
  • Example 3 The procedure was as in Example 3, with the difference that instead of the trans-Perinon Hostapermorange GR, the analog cis compound Permanent red TG01 from Hoechst AG (C.I. 71110) was used.
  • E1 ⁇ 2, E1 ⁇ 4, and E1 ⁇ 8 mean the exposure energies that have to be applied at a light intensity of 3 / wW / cm 2 in order to achieve a discharge from -400 V to -200 V, -100 V and -50 V, respectively.

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  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Health & Medical Sciences (AREA)
  • Emergency Medicine (AREA)
  • Photoreceptors In Electrophotography (AREA)
  • Light Receiving Elements (AREA)
  • Hybrid Cells (AREA)
  • Steroid Compounds (AREA)

Claims (13)

1. Matériau de reproduction électrophotographique, composé d'un support de couches conducteur de l'électricité, éventuellement d'une couche d'arrêt isolante, et d'une couche photoconductrice, la couche photoconductrice contenant au moins un pigment organique conducteur de type n, au moins un liant électroniquement inerte contenant des groupes carbonyle, et un photoconducteur, caractérisé en ce que la couche photoconductrice contient le pigment organique conducteur de type n, choisi parmi les trans- périnones, les diimides d'acide pérylène-tétracarboxylique ou les quinones condensées, à une concentration comprise entre 10 et 50% en poids, par rapport au poids de la couche, et en tant que photoconducteur, un photoconducteur exclusivement organique conducteur de type p, à une concentration allant jusqu'à 20 % en poids, par rapport au poids de la couche.
2. Matériau de reproduction selon la revendication 1, caractérisé en ce que le pigment organique conducteur de type n est présent à une concentration comprise entre 15 et 30% en poids, et le photoconducteur organique conducteur de type p est présent à une concentration allant de 2 à 8% en poids, par rapport au poids de la couche.
3. Matériau de reproduction selon la revendication 1 ou 2, caractérisé en ce que le pigment organique conducteur de type n est l'orangé Hostaperm GR (C.I. 71105).
4. Matériau de reproduction selon la revendication 1 ou 2, caractérisé en ce que le pigment organique conducteur de type n est le diimide de l'acide N,N'-diméthylpérylène-3,4,9,10-tétracarboxylique (C.I. 71130).
5. Matériau de reproduction selon la revendication 1 ou 2, caractérisé en ce que le pigment organique conducteur de type n est le diimide de l'acide N,N'-bis-(méthoxypropyl)- pérylène-3,4,9,10-tétracarboxylique.
6. Matériau de reproduction selon la revendication 1, caractérisé en ce que leliant électroniquement inerte, contenant des groupes carbonyle, est soluble ou dispersable dans une solution aqueuse alcaline.
7. Matériau de reproduction selon la revendication 6, caractérisé en ce que le liant électroniquement inerte, contenant des groupes carbonyle, est un copolymère de méthacrylates et acide méthacrylique, éventuellement avec d'autres monomères tels qu'acide acrylique et styrène.
8. Matériau de reproduction selon la revendication 7, caractérisé en ce que le liant électroniquement inerte, contenant des groupes carbonyle, a une température de transition vitreuse supérieure à 40°C.
9. Matériau de reproduction selon la revendication 1, caractérisé en ce que le support de couches conducteur de l'électricité est constitué d'aluminium.
10. Matériau de reproduction selon la revendication 1, caractérisé en ce que le support de couches conducteur de l'électricité est constitué de cuivre ou comporte une surface de cuivre.
11. Matériau de reproduction selon la revendication 1, caractérisé en ce que la couche photoconductrice a été appliquée sur le support de couches conducteur de l'électricité par pelliculage à chaud et sous pression, à partir d'un support intermédiaire.
12. Matériau de reproduction selon la revendication 1, caractérisé en ce que la couche photoconductrice est composée d'une couche inférieure qui contient un pigment organique conducteur de type n et un liant électroniquement inerte, et d'une couche de recouvrement qui contient un pigment organique conducteur de type n, un liant électroniquement inerte et un photoconducteur organique, conducteur de type p.
13. Matériau de reproduction selon la revendication 12, caractérisé en ce que la couche inférieure et la couche de recouvrement sont présentes en un rapport des poids de couche compris entre 10:1 et 1:10.
EP85105785A 1984-05-15 1985-05-10 Matériau d'enregistrement électrophotographique Expired - Lifetime EP0161648B2 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AT85105785T ATE29603T1 (de) 1984-05-15 1985-05-10 Elektrophotographisches aufzeichnungsmaterial.

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE3417951 1984-05-15
DE19843417951 DE3417951A1 (de) 1984-05-15 1984-05-15 Elektrophotographisches aufzeichnungsmaterial

Publications (3)

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EP0161648A1 EP0161648A1 (fr) 1985-11-21
EP0161648B1 EP0161648B1 (fr) 1987-09-09
EP0161648B2 true EP0161648B2 (fr) 1993-11-03

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EP85105785A Expired - Lifetime EP0161648B2 (fr) 1984-05-15 1985-05-10 Matériau d'enregistrement électrophotographique

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US (1) US4668600A (fr)
EP (1) EP0161648B2 (fr)
JP (1) JPS60254142A (fr)
AT (1) ATE29603T1 (fr)
AU (1) AU574626B2 (fr)
BR (1) BR8502270A (fr)
CA (1) CA1259517A (fr)
DE (2) DE3417951A1 (fr)
ES (1) ES8607576A1 (fr)
FI (1) FI851884L (fr)
ZA (1) ZA853586B (fr)

Families Citing this family (18)

* Cited by examiner, † Cited by third party
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DE3532346A1 (de) * 1985-09-11 1987-03-12 Hoechst Ag Verfahren zum herstellen von druckformen
JP2729616B2 (ja) * 1986-10-17 1998-03-18 富士ゼロックス株式会社 電子写真感光体
US4999272A (en) * 1988-08-31 1991-03-12 Canon Kabushiki Kaisha Electrophotographic analog and digital imaging and developing using magnetic toner
US5145759A (en) * 1989-04-21 1992-09-08 Agfa-Gevaert, N.V. Electrophotographic recording material
US5273853A (en) * 1989-06-13 1993-12-28 Mita Industrial Co., Ltd. Black photoconductive toner having sensitivity to light in the wavelength range of semiconductor lasers
JPH03146957A (ja) * 1989-11-02 1991-06-21 Iwatsu Electric Co Ltd 電子写真製版用印刷版
JP2717584B2 (ja) * 1989-11-17 1998-02-18 富士写真フイルム株式会社 電子写真式製版用印刷原版
US5069992A (en) * 1989-11-17 1991-12-03 Fuji Photo Film Co., Ltd. Electrophotographic printing plate precursor containing alkali-soluble polyurethane resin as binder resin
EP0430235B1 (fr) * 1989-11-30 1996-02-21 Mita Industrial Co. Ltd. Elément photosensible électrophotographique
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Also Published As

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CA1259517A (fr) 1989-09-19
ES543034A0 (es) 1986-06-01
ES8607576A1 (es) 1986-06-01
EP0161648B1 (fr) 1987-09-09
EP0161648A1 (fr) 1985-11-21
ZA853586B (en) 1985-12-24
FI851884L (fi) 1985-11-16
AU4251385A (en) 1985-11-21
FI851884A0 (fi) 1985-05-13
DE3560608D1 (en) 1987-10-15
US4668600A (en) 1987-05-26
AU574626B2 (en) 1988-07-07
JPS60254142A (ja) 1985-12-14
DE3417951A1 (de) 1985-11-21
BR8502270A (pt) 1986-01-14
ATE29603T1 (de) 1987-09-15

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