EP0137218B1 - Matériau d'enregistrement électrophotographique et procédé de sa préparation - Google Patents

Matériau d'enregistrement électrophotographique et procédé de sa préparation Download PDF

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Publication number
EP0137218B1
EP0137218B1 EP84109609A EP84109609A EP0137218B1 EP 0137218 B1 EP0137218 B1 EP 0137218B1 EP 84109609 A EP84109609 A EP 84109609A EP 84109609 A EP84109609 A EP 84109609A EP 0137218 B1 EP0137218 B1 EP 0137218B1
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EP
European Patent Office
Prior art keywords
layer
recording material
photoconductor
support
dye
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Expired
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EP84109609A
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German (de)
English (en)
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EP0137218A1 (fr
Inventor
Karl-Friedrich Dr. Dössel
Jürgen Dr. Lingnau
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Hoechst AG
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Hoechst AG
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Publication of EP0137218A1 publication Critical patent/EP0137218A1/fr
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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
    • G03G5/14—Inert intermediate or cover layers for charge-receiving layers

Definitions

  • the present invention relates to an electrophotographic recording material composed of an electrically conductive layer support, optionally an insulating barrier layer and a photoconductive double layer made of organic photoconductor, binder, dye and conventional additives, and a process for the production thereof.
  • the material then consists of an electrically conductive layer support, a charge generation layer and a charge transport layer.
  • the layer generating the charge carrier can consist of a dispersed pigment. If an insulating binder is used with the dispersed pigment, a volume concentration of at least 25% pigment is required.
  • the ratio of the layer thicknesses of the charge transport layer to the layer generating the charge carrier is 2: 1 to 200: 1.
  • DS-OS 21 60 812 corresponding to US Pat. No. 4,026,704
  • cover layer consists of a binder and up to 50 percent by weight of photoconductor.
  • the layer thicknesses are given as 0.1 to 511 m for the underlayer and 5 to 20 ⁇ m for the top layer.
  • a three-layer photoreceptor is described in German Offenlegungsschrift No. 31 08 618 (corresponding to US Pat. No. 4,340,658), in which a pigment concentration of 50 to 95 percent by weight in the binder used is necessary.
  • a disadvantage of the known electrophotographic recording materials with binder, organic photoconductor, dye or pigment is their relatively unsatisfactory resolution, which is particularly evident when developing a latent image charged with negative polarity with a liquid developer. Individual lines with a line width of less than 60 ⁇ m are only depicted with reduced contrast and lines of less than 40 ⁇ m are no longer displayed at all. These loss of resolution also occur with correspondingly fine screen dots.
  • Another disadvantage is the relatively high content of photoconductor.
  • the photoconductive layers must contain the organic photoconductor in a total concentration of 40 to 50 percent by weight in order to achieve sufficient photosensitivity, which is noticeable in a considerable increase in the cost of the materials.
  • the photoconductive double layer comprises the primer and the top layer
  • the primer consists of a high-molecular substance which carries alkali-solubilizing groups as a highly insulating binder
  • the top layer consists of a high molecular weight, alkali-solubilizing group-carrying substance as a highly insulating binder in which at least one photoconductor in amounts of 25 to 60 percent by weight, based on the layer, and at least one dye dissolved or dispersed in a concentration of 0.5 to 20 percent by weight, based on the layer contains that a mixing zone of substances in the range of 1.5 to 2 ⁇ m, obtained by dissolving processes during manufacture, is present in the boundary region of both layers, and that the layer thicknesses of the primer and top layer are in the ratio of 3: 1 to 1: 10, preferably in a ratio of 2: 1 to 1: 3.
  • the recording material according to the invention is used for printing purposes, the high proportion of binder in the primer ensures rapid stripping. At the same time, the low proportion of photoconductors leads to better technical feasibility of the process.
  • the use of the dye in the top layer also prevents the particles from being embedded in the pores of the substrate surface. Even with low layer weights for the photoconductive double layer, the technically required charges can be achieved with the recording material according to the invention. This is especially true when materials are used as layer supports that previously had considerable difficulties with charging, such as copper surfaces.
  • FIGS. 1 and 2 The schematic structure of the electrophotographic recording material according to the invention is shown in FIGS. 1 and 2.
  • a material which consists of an electrically conductive substrate 1, the primer 2 and the top layer 3.
  • a metallized plastic film 1, 4 is provided as a layer support on which an insulating barrier layer 5 is applied.
  • the photoconductive double layer is located on this.
  • the layer support can be in the form of a drum, a flexible band or a plate.
  • the layer support is suitable for the production of printing forms and printed circuits and consists, for example, of an aluminum, zinc, magnesium, copper, iron, nickel or a multi-metal plate.
  • Metallized, for example metal-coated, plastic films, such as aluminum-coated polyester films, or copper-clad polyimide films and plates are also suitable.
  • the surface refinement consists of mechanical or electrochemical roughening and, if appropriate, subsequent anodization and treatment with polyvinylphosphonic acid in accordance with DE-OS 16 21 478, corresponding to US Pat. No. 4,153,461.
  • the barrier layer obtained in this way is designated by position 5 in FIG.
  • a thermally, anodically or chemically generated metal oxide layer for example made of aluminum oxide, can serve as the barrier layer.
  • the function of the barrier layer is to separate the charge carrier injection from the electrically conductive one To lower or prevent layer supports in the dark in the layer producing charge carriers. On the other hand, however, it must not hinder the charge flow during the exposure process.
  • the barrier layer has a favorable influence on the adhesion of the following layers to the layer support.
  • Various natural or synthetic resin binders can be used for organic barrier layers that adhere well to a metal or aluminum surface and do not experience any detachment or detachment when the further layers are subsequently applied.
  • the thickness of the organic barrier layer is in the range of 1 ⁇ m, that of a metal oxide layer in the range of 10 to 10 3 nanometers.
  • the photoconductive double layer 2, 3 can also first be applied to an intermediate carrier (not shown), from which it is applied as a so-called dry resist to the layer carrier 1 or 1.4 transmitted subsequently or later. This can be done, for example, by lamination.
  • Plastic films such as those made of polyester, in particular of polyethylene terephthalate, have proven particularly useful as intermediate carriers. The polarity of the charging of laminated layers allows the use of positively controlled dry or liquid developers in the manufacture of printed circuits.
  • Layer 2 consists of a highly insulating binder or mixture of binders.
  • natural and synthetic resins are suitable as binders, which can be dissolved or swelled by customary solvents or solvent mixtures during the production of the layers.
  • These include polyester resins, which are mixed polyesters made from iso- and terephthalic acid with glycols. Silicone resins have also proven to be suitable. Polycarbonate resins can be used well. Binders which are soluble in aqueous or alcoholic solvent systems, optionally with the addition of acid or alkali, are particularly preferred for the production of printing forms and printed circuits. Aromatic or aliphatic, easily flammable solvents are excluded for physiological and safety reasons.
  • Suitable resin binders are high-molecular substances that carry alkali-solubilizing groups. Examples are acid anhydride, carboxyl, carboxamide, phenol, sulfonic acid, sulfonamide or sulfonimide groups. Resin binders with high acid numbers are preferably used. Copolymers with anhydride groups can be used with good success, since the lack of free acid groups means that the dark conductivity is low, despite good alkali solubility. Copolymers of styrene and maleic anhydride, sulfonyl urethanes according to German Offenlegungsschrift No. 32 10 577, and copolymers of acrylic or methacrylic acid have proven particularly useful.
  • the layer In order to enable the coating quality to be checked when applying the primer, it has proven advantageous to dye the layer with small amounts of a dye, up to about 0.5 percent by weight, based on the layer. Both the sensitizing dyes used in the top layer and dyes without sensitizing properties can be used as dyes.
  • the preferred colorants are N, N'-dimethylperylene-3,4,9,10-tetracarboxylic acid diimide (CI 71 130), copper-containing phthalocyanine (C.1. 74 160), Hostapermorange GR (CI 71 105) and / or Hostapermscharlach GO ( CI 59 300) used.
  • Soluble dyes such as rhodamine B (C.I. 45 170), astrazone orange R (C.I. 48 040) and / or brilliant green (C.I. 42 040) are preferably used.
  • Layer 3 also contains at least one photoconductive organic compound.
  • Compounds which have an extensive n-electron system are particularly suitable. These include monomeric heterocyclic compounds which are substituted by dialkyl-substituted amino groups or alkoxy groups. Heterocyclic compounds such as oxdiazole derivatives, which are mentioned in German patent 10 58 836, corresponding to US Pat. No. 3,189,447, have proven particularly useful. This subheading also includes triphenylamine derivatives, oxazole, pyrazoline, triazole and imidazole derivatives, as described, for example, in DE-PS 11 20 875.10 60 260.10 60 714 (corresponding to US Pat. Nos.
  • Hydrazone compounds such as those mentioned, for example, in DE-OS 29 19 791, corresponding to US Pat. No. 4,278,747, can also be used.
  • 2,5-Bis- (4'-dimethylaminophenyl) -1,3,4-oxdiazole, p-methoxybenzaldehyde diphenylhydrazone and / or 1,5-diphenyl-3-p-methoxyphenylpyrazoline are preferably used.
  • the compounds described for the primer are used as binders.
  • the layers contain substances that are added to the coating solution and thereby improve the surface structure and flexibility.
  • these can be, for example, plasticizers, such as triphenyl phosphate, or leveling agents, such as silicone oils.
  • the border area between the primer and the top layer there is a mixing zone of substances of both layers. It is obtained essentially by the fact that when the second layer is applied, layer components, in particular photoconductors, get into the layer applied first by diffusion.
  • the mixing zone is about 1.5 to 2 ⁇ m, which can be determined, for example, by the fact that photoconductor components do not diffuse so deeply that so-called poisoning phenomena can be recognized by the layer support, as long as the layer thickness of the layer initially applied is chosen to be over 2 ⁇ m.
  • the total layer thicknesses of the photoconductive double layer lie in the range between approximately 4 to 50 ⁇ m. In the case of use for printing plates, the total layer thickness is preferably in the range from 4 to 10 ⁇ m. When used for printed circuits, the total layer thicknesses are in the range from 6 to 50 ⁇ m.
  • the present invention also relates to a method for producing the electrophotographic recording material according to the invention, in which the photoconductive double layer is applied to the electrically conductive support.
  • the process is characterized in that the coating solution or dispersion of the primer is applied and dried or dried, and then the coating solution or dispersion of the top layer is covered and dried while the previous layer is dissolved.
  • the drying of the double layer is preferably carried out in stages in relation to duration and temperature.
  • the duration of the individual steps is in the range of about 10 seconds to a few minutes.
  • the drying temperature is in the range from room temperature to 130 ° C.
  • a method has proven particularly useful in which the applied solutions or dispersions are dried gradually in the range from room temperature to 130 ° C. in time intervals of 5 to 30 seconds.
  • Solvents or solvent mixtures with boiling temperatures are used for the coating solution, which enable drying in the technically customary range and those which have good solution properties for photoconductors and binders and which are somewhat environmentally friendly. These include lower alcohols, lower ketones and ethers or also esters. Examples include: tetrahydrofuran, acetone, methyl glycol and butyl acetate. It has been found that fast-drying coating solutions or dispersions advantageously contain tetrahydrofuran as the solvent.
  • the process of dissolving the layer applied first takes place at a relatively low temperature. This is followed by drying, preferably in stages in the temperature range from 80 to 120 ° C.
  • the coatings are applied in a customary manner, for example by knife or spray application.
  • the application is preferably made with a flow machine.
  • the layers are dried, for example, in drying channels, the various drying stages being determined by the temperature of the individual areas, by the running speed of the material and by the prevailing air throughput.
  • the invention is illustrated by the following examples and comparative examples.
  • the liquid top layer was dried at room temperature for about 20 seconds, then at 60 ° C. for 30 seconds and then at 110 ° C. for about 120 seconds. Under these conditions, the primer was loosened and a targeted mixing zone between the two layers was achieved.
  • the top layer was adjusted so that the total layer weight of the double layer was 6 g / m 2 , which corresponds to a thickness of about 6 ⁇ m.
  • the double layers produced in this way are distinguished by a high sensitivity to light with positive charging and by a very good resolution. Corresponding information can be found in the table.
  • the E 1 ⁇ 2 values refer to exposure with halogen lamps when using heat protection filters.
  • Example 2 The procedure was as in Example 1, with the difference that a mixture of 50% binder and 50% 2,5-bis (4'-dimethylaminophenyl) -1,3,4-oxdiazole was used in the primer instead of the pure binder .
  • the recording material obtained in this way has, in spite of a significantly increased photoconductor content, an insignificantly higher sensitivity compared to Example 1 with a significantly impaired removal properties.
  • the layer was applied to anodized aluminum printing plate supports, as in Example 1, so that a layer weight of 6 g / m 2 was achieved after drying.
  • composition of the layer corresponds to the combination of 3 g / m 2 of primer and 3 g / m 2 of top layer in Example 1.
  • the photosensitivity is reduced compared to the double layer from Example 1, and the resolution of the images produced on this layer is significantly worse than on the double layer in Example 1.
  • the 40 ⁇ m lines were not reproduced.
  • Example 1 The coatings of Example 1 were repeated, except that instead of the anodized aluminum carrier, a copper-clad polyimide film, as used for the production of flexible printed circuit boards in electronics, was used.
  • the double layers with 0.5, 1.0 and 1.5 g / m 2 primer could not yet be charged to the technically desired +500 V. These layers were therefore not very suitable for practical use.
  • the coatings with primers in the range from 2 g / m 2 to 4.5 g / m 2 led to charges of over +500 V. In this way, toner images with high resolution could be obtained. These films could then be processed into high-quality, flexible printed circuit boards by stripping the areas not covered by toner and etching away the metal areas underneath.
  • the ratio of the layer thicknesses of the primer to the top layer is in the favorable range between 1: 2 and 3: 1.
  • This example also shows that in the coating technique described there is a mixing zone between the primer and the top layer of at least 1.5 ⁇ m in thickness, which is of crucial importance for the electrophotographic behavior of the double layer according to the invention.
  • Example 2 The coating of Example 2 was repeated, except that a copper-clad polyimide film as in Example 4 was used instead of the anodized aluminum support.
  • the electrophotographic recording material thus produced could only be charged to less than +100 V and was therefore unsuitable for practical use. It is believed that when the solution of the photoconductor comes into contact with the copper surface, "poisoning" of the photoconductor occurs.
  • a polyester film 75 1 1m thick was used as an intermediate carrier with a solution of
  • the top layer was dried for about 30 seconds at 60 ° C. and then for about 120 seconds at 100 ° C. A targeted mixing zone between the two layers was achieved under these conditions.
  • the dry layer weight of the double layer was 6 g / m 2 .
  • the double layer was then transferred to a copper-clad epoxy circuit board in a laminator at 120 ° C.
  • the electrophotographic recording material thus produced had high charging and excellent photosensitivity. It was charged negatively, exposed imagewise, treated with a liquid developer and the resulting toner image was fixed at 160 ° C. by heating. The toner image showed a very good resolution. The image areas not covered by the toner were removed with an aqueous alkaline stripper as described in DE-OS 28 17 428. corresponding to US Pat. No. 4,252,880, Example 1, and the exposed copper surfaces were then etched away. This gave a high-quality printed circuit board.
  • the light sensitivity of the recording material described is so great that exposure to a laser with low output is also possible.
  • a polyester film 75 1 1m thick was used as an intermediate carrier with a solution of
  • the coating was dried, the solution application being adjusted to a dry layer weight of 3 g / m 2 .
  • This layer was dried for about 30 seconds at 60 ° C. and then for about 120 seconds at 100 ° C. A targeted mixing zone between the two layers was achieved under these conditions.
  • the total dry layer weight was 6 g / m 2 .
  • the double layer was then transferred in a laminator at 120 ° C from the intermediate carrier to a bare aluminum foil.
  • the electrophotographic recording material thus produced had a high charge (table) and an excellent panchromatic sensitivity to negative charge
  • Example 7 The procedure was as in Example 7, except that the order of the coatings was reversed and that the coating was carried out directly on a bare aluminum foil 75 1 1m thick.
  • the material obtained in this way therefore corresponded to the recording material from Example 7 in terms of the layer structure - aluminum support, top layer and primer.
  • the material described here had less than half the photosensitivity of the material according to the invention from Example 7. This is due to the insufficient formation of a mixing zone between Top coat and primer. While in example 7 the easily diffusible photoconductor is in solution and can therefore easily penetrate into the swollen or dissolved primer, in this example the photoconductor must also be detached with subsequent diffusion in addition to the swelling of the primer. This is not possible in reasonable periods.
  • Example 2 The procedure was as given in Example 1, with the difference that instead of the anodized aluminum support, an aluminum-vapor-coated polyester film, instead of the N, N'-dimethylperylene-3,4,9,10-tetracarboxylic acid diimide Hostapermorange GR (Cl 71 105), and instead of 2,5-bis- (4'-dimethylaminophenyl) -1,3,4-oxdiazole 1,3-diphenyl-5-p-methoxy-phenyl-pyrazoline and instead of the copolymer of styrene and maleic anhydride, a copolymer of styrene, Methacrylic acid and hexyl methacrylate, monomer ratio 10:30:60 was used.
  • Hostapermorange GR Cl 71 105
  • Example 9 The procedure was as in Example 9, with the difference that instead of the Hostapermorange GR Hostapermscharlach GO (C.I. 59 300) and p-methoxybenzaldehyde-diphenylhydrazone was used as the photoconductor.
  • Hostapermorange GR Hostapermscharlach GO (C.I. 59 300) and p-methoxybenzaldehyde-diphenylhydrazone was used as the photoconductor.
  • the measured data for charging and sensitivity are shown in the table.
  • the coating was dried and had a dry layer weight of 3 g / m 2 .
  • Example 2 Drying was carried out in stages, as described in Example 1.
  • the l dry coating weight amounted to about 6 g / m 2.
  • the recording material thus produced was charged to +800 V, showed a good light sensitivity and led after imagewise exposure and toning with a liquid developer to images of very high resolution.
  • a printing plate produced from this after fixing and stripping gave a print run of over 100,000 with good tonal value reproduction.
  • the dry layer weight was again approx. 6 g / m 2 .
  • the recording material produced in this way could be charged to +700 V and showed, despite a doubled photoconductor component compared to Example 11 Complete layer only a comparable light sensitivity.
  • Example 11 If the printing plate described here is treated with an aqueous alkaline stripper in a commercial stripping device, the layer can only be stripped slowly because of its high proportion of insoluble photoconductor. The disk throughput is low. The recording material of Example 11 according to the invention can be stripped three times as quickly.

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  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Photoreceptors In Electrophotography (AREA)

Claims (17)

1. Matériau de reproduction électrophotographique composé d'un support de couche conducteur de l'électricité, éventuellement d'une couche d'arrêt isolante, et d'une double couche photoconductrice constituée de photoconducteur organique, liant, colorant et additifs usuels, caractérisé en ce que la double couche photoconductrice comprend une première couche et une couche de recouvrement, en ce que la première couche est composée, en tant que liant hautement isolant, d'une substance à haut poids moléculaire, portant des groupes solubilisateurs dans les alcalis, en ce que la couche de recouvrement est composée, en tant que liant hautement isolant, d'une substance à haut poids poids moléculair, portant des groupes solubilisateurs dans les alcalis, liant qui contient au moins un photoconducteur en quantités de 25 à 60 % en poids, par rapport à la couche, et au moins un colorant dissous ou dispersé à une concentration de 0,5 à 20 % en poids, par rapport à la couche, en ce que, à l'interface des deux couches, est présente une zone de mélange des substances dans la plage de 1,5 à 2 lim, obtenue par des processus de dissolution partielle lors de la fabrication, et en ce que les épaisseurs de la première couche et de la couche de recouvrement sont dans un rapport allant de 3:1 à 1:10.
2. Matériau de reproduction selon la revendication 1, caractérisé en ce que la première couche contient jusqu'à 0,5 % en poids, par rapport à la couche, de colorant dissous ou dispersé.
3. Materiau de reproduction selon les revendications 1 ou 2, caractérisé en ce qu'il a été obtenu par transfert de la double couche photoconductrice, à partir d'un support intermédiaire, sur le support de couche conducteur de l'électricité, éventuellement muni d'une couche d'arrêt.
4. Materiau de reproduction selon la revendication 1, caractérisé en ce que le colorant de la couche de recouvrement est choisi parmi des dérivés de l'acide pérylène-3,4,9-10-tétracarboxylique, les phtalocyanines métallifères, les périnones, les quinones condensées, les colorants rhodamine, les colorants cyanine et/ou les colorants triarylméthane.
5. Matériau de reproduction selon la revendication 4, caractérisé en ce que sont présents en tant que colorant le diimide de l'acide N,N'-diméthyl-pérylène-3,4,9,10-tétra- carboxylique (C.1. 71 130), la phtalocyanine métallifère (C.1. 74160), l'orangé Hostaperm GR (C.1. 71 105) et/ou l'écarlate Hostaperm GO (C.1. 59 300).
6. Matériau de reproduction selon la revendication 4, caractérisé en ce que sont présents en tant que colorant la rhodamine B (C.I. 45 170), l'orangé d'astrazone R (C.I. 48 040) et/ou le vert brillant (C.I. 42 040).
7. Matériau de reproduction selon la revendication 1, caractérisé en ce que le support de couche est métallique ou est constitué d'une feuille de matière plastique métallisée.
8. Matériau de reproduction selon la revendication 7, caractérisé en ce que le support de couche est de l'aluminium grainé électrochimiquement et anodisé.
9. Matériau de reproduction selon la revendication 7, caractérisé en ce que le support de couche est une feuille de polyimide doublée de cuivre.
10. Matériau de reproduction selon la revendication 1, caractérisé en ce que le photoconducteur est choisi parmi les oxadiazoles, oxazoles, pyrazolines, triazoles, imidazoles, hydrazones.
11. Matériau de reproduction selon la revendication 10, caractérisé en ce que le photoconducteur est le 2,5-bis-(4'-diméthylaminophényl)-1,3,4-oxadiazole.
12. Matériau d'enregistrement selon la revendication 10, caractérisé en ce que le photoconducteur est la p-méthoxybenzaldéhyde- diphénylhydrazone.
13. Matériau de reproduction selon la revendication 10, caractérisé en ce que le photoconducteur est la 1,5-diphényl-3-p-méthoxyphenyl-pyrazoline.
14. Matériau de reproduction selon la revendication 1, caractérisé en ce que les épaisseurs de couche de la première couche et de la couche de recouvrement sont dans un rapport allant de 2:1 à 1:3.
15. Matériau de reproduction selon la revendication 1, caractérisé en ce que le liant hautement isolant est un copolymère de styrène et d'anhydride maléique, un sulfonyl-uréthanne et/ou un copolymère de l'acide acrylique et/ou de l'acide méthacrylique.
16. Procedé pour la fabrication du matériau de reproduction électrophotographique selon la revendication 1, dans lequel on applique la double couche photoconductrice sur le support conducteur de l'électricité, caractérisé en ce que l'on applique la solution ou dispersion de revêtement pour la première couche et on la sèche ou sèche partiellement, et on applique ensuite sur celle-ci la solution ou dispersion de revêtement pour la couche de recouvrement et on la sèche avec dissolution partielle de la couche précédente.
17. Procédé selon la revendication 16, caractérisé en ce que le séchage des solutions ou disperions appliquées est effectué dans la gamme allant de la température ambiante à 130°C, et par intervalles de 5 à 30 secondes. i
EP84109609A 1983-08-16 1984-08-13 Matériau d'enregistrement électrophotographique et procédé de sa préparation Expired EP0137218B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19833329441 DE3329441A1 (de) 1983-08-16 1983-08-16 Elektrophotographisches aufzeichnungsmaterial und verfahren zu seiner herstellung
DE3329441 1983-08-16

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EP0137218A1 EP0137218A1 (fr) 1985-04-17
EP0137218B1 true EP0137218B1 (fr) 1987-09-23

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Publication number Priority date Publication date Assignee Title
DE19510526A1 (de) * 1995-03-23 1996-09-26 Hoechst Ag Elektrophotographisches Aufzeichnungsmaterial für die Herstellung von Druckplatten

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Publication number Priority date Publication date Assignee Title
US3814600A (en) * 1970-06-30 1974-06-04 Eastman Kodak Co Electrophotographic element
DE2237539C3 (de) * 1972-07-31 1981-05-21 Hoechst Ag, 6000 Frankfurt Elektrophotographisches Aufzeichnungsmaterial
JPS5389434A (en) * 1977-01-17 1978-08-07 Mita Industrial Co Ltd Stacked photosensitive body for electrophotography
JPS6035057B2 (ja) * 1979-07-13 1985-08-12 株式会社リコー 電子写真用感光体
JPS56125748A (en) * 1980-03-08 1981-10-02 Mita Ind Co Ltd Laminated photoreceptor
JPS57124739A (en) * 1981-01-27 1982-08-03 Ricoh Co Ltd Composite electrophotographic receptor
DE3110960A1 (de) * 1981-03-20 1982-09-30 Basf Ag, 6700 Ludwigshafen Elektrophotographisches aufzeichnungsmaterial
JPS58102239A (ja) * 1981-12-14 1983-06-17 Fuji Photo Film Co Ltd 光導電性組成物およびそれを用いた電子写真感光材料

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DE3466441D1 (en) 1987-10-29
EP0137218A1 (fr) 1985-04-17
US4654283A (en) 1987-03-31

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