EP0137217B1 - 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
EP0137217B1
EP0137217B1 EP84109608A EP84109608A EP0137217B1 EP 0137217 B1 EP0137217 B1 EP 0137217B1 EP 84109608 A EP84109608 A EP 84109608A EP 84109608 A EP84109608 A EP 84109608A EP 0137217 B1 EP0137217 B1 EP 0137217B1
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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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EP84109608A
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German (de)
English (en)
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EP0137217A1 (fr
Inventor
Karl-Friedrich Dr. Dipl.-Chem. Dössel
Jürgen Dr. Dipl.-Chem. Lingnau
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Hoechst AG
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Hoechst AG
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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
    • G03G5/043—Photoconductive layers characterised by having two or more layers or characterised by their composite structure
    • G03G5/047—Photoconductive layers characterised by having two or more layers or characterised by their composite structure characterised by the charge-generation layers or charge transport 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 consisting of a charge carrier-generating and a charge transport layer, consisting 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.
  • a three-layer photoreceptor is described in German Offenlegungsschrift No. 31 08 618 (corresponding to US Pat. No. 4,340,655), 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 l are no longer displayed at all with only reduced contrast and lines with a line width of less than 40 ⁇ m. These loss of resolution also occur with correspondingly fine vice points.
  • 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 charge carrier-producing layer consists of a highly insulating binder consisting of a compound containing high molecular weight, alkali-solubilizing groups, containing 0.5 to 20 percent by weight of dye are contained on the layer, dissolved or dispersed
  • the charge transport layer consists of a highly insulating binder composed of a high-molecular compound containing alkali-solubilizing compound, in which at least one photoconductor is dissolved in amounts of 25 to 60 percent by weight, based on the layer, and the dye or dispersed in a concentration of at most 5 percent by weight, based on the layer, that a mixing zone of substances in the range from 1.5 to 2 ⁇ m, obtained by dissolving processes during production, is present in the boundary region of the two layers, and that the layer thicknesses of the charge-generating layer and charge transport layer are in a ratio of 3: 1 to 1:10, preferably
  • recording materials can be made available which are able to meet high demands and enable high resolution with a relatively low photoconductor concentration, based on the total layer.
  • the recording material according to the invention is used for printing purposes, the high proportion of binder in the charge-generating layer ensures rapid stripping.
  • the low proportion of photoconductors leads to better technical feasibility of the process.
  • the use of relatively low dye concentrations in the layer generating the charge carrier also prevents the particles from being embedded in the pores of the surface of the layer support. 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.
  • FIG. 1 shows a material which consists of an electrically conductive layer support 1, the charge generation layer 2 and the charge transport 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 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 barrier layer has the task of reducing or preventing the charge carrier injection from the electrically conductive layer support into the charge generation layer in the dark. On the other hand, however, it must not hinder the charge flow during the exposure process.
  • the adhesion of the following layers to the layer support is favorably influenced by the barrier layer.
  • 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 111 m, that of a metal oxide layer in the order 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.
  • Layer 2 contains at least one dye as the charge carrier-generating layer.
  • the dye can be either dissolved or dispersed in the layer in the layer.
  • the connections are known. This subheading includes, in particular, dyes from the class of the perylene-3,4,9,10-tetracarboxylic acid derivatives according to DE-PS 22 37 539, corresponding to US Pat. No. 3 871 882, of the metal-containing phthalocyanines according to, for example, DE-OS 32 45 637, the perinones according to DE-AS 22 39 923, corresponding to GB-PS 1 416 603, and / or the fused quinones according to DE-AS 22 37 678, corresponding to US-PS 4 315 981.
  • Possible soluble dyes are: rhodamine dyes, cyanine dyes and / or triarylmethane dyes.
  • the preferred colorants are N, N'-dimethylperylene-3,4,9,10-tetracarboxylic acid diimide (C.1. 71 130), copper-containing phthalocyanine (C.1. 74 160), Hostapermorange GR (C.1. 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.
  • Suitable compounds in the charge transport layer 3 which serve to transport the charge are, in particular, those which have an extensive n-electron system. 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 highly insulating binder for the charge generation layer and for the charge transport layer can be the same or different.
  • natural and synthetic resins are suitable as such, which can be dissolved or swelled by customary solvents or solvent mixtures during the production of the layers.
  • polyester resins which are mixed polyesters of 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 patent application, file number P 32 10 577.0 and copolymers of acrylic or methacrylic acid have proven particularly useful.
  • 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 of the charge carriers generating layer and the charge transport 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 approximately 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 thickness of the photoconductive double layer are in the range between about 4 to 50 li 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 which are GESAM t layer thicknesses in the range of 6 to 50 l im.
  • 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 layer generating the charge carrier is applied and dried or dried, and then the coating solution or dispersion of the charge transport layer is covered with a layer and dried while dissolving the first layer.
  • 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 in stages in the range from room temperature to 130 ° C. in time intervals of 5 to 30 seconds.
  • a mixing zone of the substances results in a thickness of about 1.5 to 2 ⁇ m, which in particular favors the generation of charge carriers.
  • Solvents or solvent mixtures with boiling temperatures are used for the coating solution, which allow drying in the technically customary range and those which have good solution properties for photoconductors and binders and which are to a certain extent 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 coating was dried.
  • the liquid top layer was dried for about 10 seconds at room temperature, then for 30 seconds at 60 ° C. and then for about 120 seconds at 110 ° C. Under these conditions, the layer generating the charge carrier was dissolved and a targeted mixing zone was achieved. The request of the charge transport layer was like this adjusted that the total layer weight was 6 g / m 2 , which corresponds to a thickness of 6 li m.
  • the E 1/2 values refer to exposure with halogen lamps when using heat protection filters.
  • the printing plate obtained after imaging, development with a commercially available liquid developer, fixation and stripping in accordance with the information in DE-AS 11 17 391 produced a print run of well over 100,000 with good tonal value reproduction; in the K field of the PMS wedge, the 20 l were reproduced in the line.
  • the dispersion was applied to a printing plate support according to Example 1 so that a layer weight of g / m 2 was reached after drying.
  • the composition of the layer corresponded to the combination of 3 g / m 2 of the charge carrier-generating layer and 3 g / m 2 of the charge transport layer from Example 1.
  • the sensitivity (E 1/2 ) - 1 is significantly reduced compared to the layer from Example 1, and the resolution of the images produced on this material is significantly worse than on the material according to example 1. in the K field of the PMS wedge was achieved not playing the 40 li mexcellentm.
  • Example 1 The coatings of Example 1 were repeated, except that a copper-clad polyimide film, as used for the production of flexible printed circuit boards in electronics, was used instead of the printing plate support mentioned there.
  • the double layers with layers of 0.5, 1.0 and 1.5 g / m 2 of charge carriers could not yet be charged to over -500 V. These layers were therefore not suitable for practical use.
  • the coatings with layers in the range of 2 g / m 2 to 4.5 g / m 2 resulted in charges of over -500 V. After charging, exposure and development with a liquid developer, high-resolution toner images could be obtained. These foils could then be processed into high-quality flexible printed circuit boards by stripping and etching away the non-image areas.
  • the ratio of the layer thicknesses of the layer generating the charge carrier to the charge transport layer between 2: 1 and 1: 3 is technically particularly favorable.
  • Example 2 The coating of Example 2 was repeated, except that a copper-clad polyimide film from Example 3 was used instead of the aluminum printing plate 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 poisoning occurs on a copper surface. The problem of the lack of chargeability of thin layers (6 g / m 2 ) also occurred when coating solutions with other photoconductors, such as oxazole, pyrazoline and hydrazone compounds, on copper-containing materials. A similar, if not so pronounced loss of chargeability also resulted when coating on iron- or nickel-containing materials. It has been recognized that this loss of charge can be avoided by introducing a photoconductor-free, charge carrier-generating layer in contact with corresponding metal surfaces.
  • Example 3 show that in the coating technique described here, when the charge-generating layer is detached, a mixing zone between the two layers of about 1.5 to 2 ⁇ m thick is formed.
  • 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 dry layer weight of this double layer recording material was 6 g / m 2.
  • This layer was dried for about 30 seconds at 60 ° C. and then for about 120 seconds at 100 ° C.
  • the double layer was then transferred to a bare aluminum foil in a laminator at 120 ° C.
  • the electrophotographic recording material thus produced had a high charge acceptance (table) and an excellent spectral sensitivity in the range from 400 to 800 nm with positive charging.
  • Example 6 The procedure was as in Example 6, except that the order of the coatings was reversed and carried out without dissolving and that the coating was carried out directly on an aluminum foil.
  • the material obtained in this way therefore corresponded to the material from Example 6 in the layer structure - aluminum carrier, charge transport layer with binder / photoconductor and charge carrier-generating layer from binder / pigment.
  • This material had less than half the sensitivity of the material according to the invention according to Example 6. It is believed that this is due to the insufficient formation of a mixing zone between the layers. While in example 6 the easily diffusible photoconductor is already in solution and can therefore easily penetrate into the swollen or dissolved pre-layer, in this example, besides the swelling of the pre-layer, the photoconductor must also be removed with subsequent Diffusion into the layer generating charge carriers take place. This is not possible within a reasonable period of time.
  • Example 2 The procedure was as in Example 1, with the difference that instead of 4% N, N'-dimethylperylene-3,4,9,1 0-tetracarboxylic acid diimide 5% Hostapermorange GR (CI 71 105) was used and that the layer weight of Charge generation layer 1.5 g / m 2 and that of the charge transport layer was 4.5 g / m 2 .
  • Hostapermorange GR CI 71 105
  • Example 8 The procedure was as in Example 8, with the difference that instead of the binder in the charge-generating layer, a mixture of 80% binder and 20% 2,5-bis (4'-dimethylaminophenyl) -1,3,4-oxdiazole has been used.
  • This layer arrangement corresponds to the recording material described in DE-OS 21 60 812.
  • the table shows that the addition of the photoconductor leads to a slight reduction in sensitivity and at the same time a marked reduction in the stripping speed.
  • Example 2 The procedure was as in Example 1, with the difference that Hostapermscharlach GO (C.I. 59 300) was used instead of N, N'-dimethy) pery) en-3,4,9,10-tetracarboxylic acid diimide.
  • Hostapermscharlach GO C.I. 59 300
  • Example 2 The procedure was as in Example 1, with the difference that instead of 2,5-bis (4'-dimethylamino-phenyl) -1,3,4-oxdiazole p-methoxy-benzaldehyde-diphenylhydrazone according to DE-OS 29 19 791 was used. Charging and sensitivity of the recording materials described in Examples 8, 9, 10, 11 and 12 are included in the table.
  • the coating was dried and had a dry layer weight of 3 g / m 2 .
  • Example 2 The drying was carried out as described in Example 1.
  • the dry layer weight of this double layer was approximately 6 g / m 2 .
  • the recording material thus produced could be charged to -800 V, showed good sensitivity and, after charging, imagewise exposure, development with a liquid developer and decoating, gave rise to printing plates of high resolution.
  • the dry layer weight was approx. 6 g / m 2 .
  • the recording material produced in this way showed only a comparable sensitivity, despite the fact that the photoconductor content in the total layer was twice as high as in Example 13.
  • Example 13 If the plate described here is treated with an aqueous alkaline stripper in accordance with the specifications in DE-AS 11 17 391 in a commercial stripping device, the layer can only be removed slowly due to its high proportion of insoluble photoconductor. The disk throughput is low. The Material of Example 13 according to the invention can be stripped three times as quickly due to its lower proportion of photoconductor.
  • Example 13 a recording material consisting of a charge-generating layer (1.5 g / m 2 ) made of 38% 2,5-bis (4'-dimethylaminophenyl) -1,3,4-oxdiazole, 57% of a copolymer was from styrene and maleic anhydride and 5% rhodamine B and a charge transport layer (10 g / m 2 ) from 50% 2,5-bis (4'-dimethylaminophenyl) -1,3,4-oxdiazole and 50% of a copolymer of styrene and Maleic anhydride produced.
  • This material largely corresponds to that described in DE-OS 21 60 812, Example 3. Under the measurement conditions used in all examples (halogen lamp with heat protection filters), this double layer had a sensitivity (E 1/2 ) - 1 of (79 ⁇ J / cm 2 ) -1 .

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  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Photoreceptors In Electrophotography (AREA)
  • Light Receiving Elements (AREA)

Claims (16)

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 consistant en une couche productrice de porteurs de charge et une couche de transfert de charge, double couche constituée de photoconducteur organique, liant, colorant et additifs usuels, caractérisé en ce que la couche productrice de porteurs de charge est constituée d'un liant hautement isolant à base d'un composé à haut poids moléculaire, contenant des groupes solubilisateurs dans les alcalis, lequel liant contient, dissous ou dipersés, 0,5 à 20 % en poids de colorant, par rapport à la couche, en ce que la couche de transfert de charge est constituée d'un liant hautement isolant à base d'un composé à haut poids moléculaire, contenant 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 le colorant dissous ou dispersé à une concentration d'au plus 5 % 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 um, obtenue par des processus de dissolution partielle lors de la fabrication, et en ce que les épaisseurs de couche de la couche productrice de porteurs de charge et de la couche de transfert de charge sont dans un rapport allant de 3:1 à 1:10.
2. Matériau de reproduction selon la revendication 1, 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.
3. Matériau de reproduction selon la revendication 1, caractérisé en ce que le colorant est choisi parmi des dérivés de l'acide pérylène-3,4,9,10-tétracarboxylique, les phtalocyanines metallifères, les perinones, les quinones condensées, les colorants rhodamine, les colorants cyanine et/ou les colorants triarylméthane.
4. Matériau de reproduction selon la revendication 3, caractérisé en ce que sont présents en tant que colorant le diimide de l'acide N,N'-diméthyl-pérylène-3,4,9,10-tétracarboxylique (C.1. 71 130), la phtalocyanine métallifère (C.I. 74 160), l'orangé Hostaperm GR (C.1. 71 105) et/ou l'écarlate Hostaperm GO (C.I. 59 300).
5. Matériau de reproduction selon la revendication 3, 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).
6. 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.
7. Matériau de reproduction selon la revendication 6, caractérisé en ce que le support de couche est de l'aluminium grainé électrochimiquement et anodisé.
8. Matériau de reproduction selon la revendication 6, caractérisé en ce que le support de couche est une feuille de polyimide doublée de cuivre.
9. Matériau de reproduction selon la revendication 1, caractérisé en ce que le photoconducteur est choisi parmi des oxadiazoles, oxazoles, pyrazolines, triazoles, imidazoles, hydrazones.
10. Matériau de reproduction selon la revendication 9, caractérisé en ce que le photoconducteur est le 2,5-bis-(4'-diméthylaminophényl)-1,3,4-oxadiazole.
11. Matériau de reproduction selon la revendication 9, caractérisé en ce que le photoconducteur est la p-methoxybenzaldéhyde- diphénylhydrazone.
12. Matériau de reproduction selon la revendication 9, caracterisé en ce que le photoconducteur est la 1,5-diphényl-3-p-méthoxyphényl-pyrazoline.
13. Matériau de reproduction selon la revendication 1, caractérisé en ce que les épaisseurs de couche de la couche productrice de porteurs de charge et de la couche de transfert de charge sont dans un rapport allant de 2:1 à 1:3.
14. 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 sulfonyluréthanne et/ou un copolymère de l'acide acrylique et/ou de l'acide méthacrylique.
15. Procédé pour la fabrication du matériau de reproduction électrophotographique selon la revendication 1, dans lequel on applique la double couche photoconductrice sur le support de couche conducteur de l'électricité, caractérisé en ce que l'on applique la solution ou dispersion de revêtement pour la couche productrice de porteurs de charge et on la sèche ou sèche partiellement, et on applique ensuite sur celle-ci la solution ou dispersion de revêtement pour la couche de transfert de charge et on la sèche avec dissolution partielle de la première couche.
16. Procédé selon la revendication 15, caractérisé en ce que le séchage des couches appliquées est effectué graduellement dans la gamme allant de la température ambiante à 130°C et par intervalles de 5 à 30 secondes.
EP84109608A 1983-08-16 1984-08-13 Matériau d'enregistrement électrophotographique et procédé de sa préparation Expired EP0137217B1 (fr)

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DE19833329442 DE3329442A1 (de) 1983-08-16 1983-08-16 Elektrophotographisches aufzeichnungsmaterial und verfahren zu seiner herstellung
DE3329442 1983-08-16

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EP0137217A1 EP0137217A1 (fr) 1985-04-17
EP0137217B1 true EP0137217B1 (fr) 1987-09-23

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US (1) US4652507A (fr)
EP (1) EP0137217B1 (fr)
JP (1) JPS6076748A (fr)
AU (1) AU3195884A (fr)
DE (2) DE3329442A1 (fr)

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DE3417951A1 (de) * 1984-05-15 1985-11-21 Hoechst Ag, 6230 Frankfurt Elektrophotographisches aufzeichnungsmaterial
DE3506436A1 (de) * 1985-02-23 1986-08-28 Hoechst Ag, 6230 Frankfurt Neue sulfonhaltige styrolderivate, verfahren zu deren herstellung und deren verwendung
JPH0727265B2 (ja) * 1986-11-04 1995-03-29 ミノルタ株式会社 積層型感光体
JPH0727263B2 (ja) * 1986-11-04 1995-03-29 ミノルタ株式会社 積層型感光体
JP2516223B2 (ja) * 1987-08-31 1996-07-24 三田工業株式会社 有機感光体
JPH03113454A (ja) * 1989-09-27 1991-05-14 Mita Ind Co Ltd 電子写真用有機感光体の製造方法
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JPS6076748A (ja) 1985-05-01
US4652507A (en) 1987-03-24
AU3195884A (en) 1985-02-21
DE3466440D1 (en) 1987-10-29
DE3329442A1 (de) 1985-03-21
EP0137217A1 (fr) 1985-04-17

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