EP0066215A2 - Matériau d'enregistrement électrophotographique et procédé pour sa production - Google Patents

Matériau d'enregistrement électrophotographique et procédé pour sa production Download PDF

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Publication number
EP0066215A2
EP0066215A2 EP82104453A EP82104453A EP0066215A2 EP 0066215 A2 EP0066215 A2 EP 0066215A2 EP 82104453 A EP82104453 A EP 82104453A EP 82104453 A EP82104453 A EP 82104453A EP 0066215 A2 EP0066215 A2 EP 0066215A2
Authority
EP
European Patent Office
Prior art keywords
protective layer
recording material
layer
material according
acrylated
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
EP82104453A
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German (de)
English (en)
Other versions
EP0066215B1 (fr
EP0066215A3 (en
Inventor
Wolfgang Dr. Dipl.-Chem. Wiedemann
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Hoechst AG
Original Assignee
Hoechst AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Hoechst AG filed Critical Hoechst AG
Publication of EP0066215A2 publication Critical patent/EP0066215A2/fr
Publication of EP0066215A3 publication Critical patent/EP0066215A3/de
Application granted granted Critical
Publication of EP0066215B1 publication Critical patent/EP0066215B1/fr
Expired legal-status Critical Current

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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
    • G03G5/147—Cover layers
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
    • Y10S430/001—Electric or magnetic imagery, e.g., xerography, electrography, magnetography, etc. Process, composition, or product
    • Y10S430/10—Donor-acceptor complex photoconductor
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
    • Y10S430/162—Protective or antiabrasion layer

Definitions

  • the invention relates to an electrophotographic recording material composed of an electrically conductive layer support, optionally an insulating intermediate layer, a photoconductive system composed of at least one layer of organic materials with a charge-generating compound and charge-transporting compound and a radiation-hardened transparent protective layer, and a process for its production.
  • photoconductor layers with an additional cover layer.
  • electrophotographic recording materials European patent application No. 0 046 958 which have a photoconductor layer based on organic or inorganic substances on an electrically conductive support, over which a protective layer made of radiation-hardened, crosslinked polyester is arranged.
  • Disadvantages of these recording materials are that they consist, for example, as a photoconductor layer of less flexible layers containing selenium or selenium, in which a hardening action by UV radiation can even cause an undesirable gradual change in modification, or that photoconductor layers are used which are generally less sensitive photoconductor systems represent and be affected by the applied top layer in their photoconductor properties.
  • a recording material which has a protective layer made of a surface-abrasion-resistant binder made of polyurethane resin, polycarbonate resin, Phenoxy resin, polyacrylate or methacrylate resin or a wide variety of polyisocyanate and hydroxyl-containing acrylate or epoxy resins.
  • the binders used are both non-crosslinking, thermally postcrosslinking or self-crosslinking.
  • the protective layers are applied to the photoconductor layer by coating, dipping or, if appropriate, by electrostatic spraying with subsequent drying and, if appropriate, curing. This requires solvents which on the one hand dissolve the substances to be applied well, but which do not attack or dissolve the substances in the respective photoconductor layer.
  • the photoconductor layer located under the protective layer is dissolved to different extents and the photoconductor properties can be adversely affected thereby.
  • an electrophotographic recording material comprising an electrically conductive substrate, optionally an insulating intermediate layer, a photoconductive system composed of at least one layer of organic materials with a charge-generating compound and charge-transporting compound and a radiation-hardened, transparent protective layer, which is characterized in that the protective layer applied to the surface of the photoconductive system with the aid of a removable intermediate carrier consists of acrylated binder which is hardened by irradiation with ultraviolet light.
  • the protective layer preferably contains acrylated polyurethane, acrylated polyester or acrylated epoxy resin as the acrylated binder. Acrylated polyurethane is very particularly preferred.
  • the protective layer also contains reactive thinner and photoinitiator and is 0.1 to 10 ⁇ m thick.
  • the recording material according to the invention is produced by applying to the surface of the photoconductive system a protective layer located on an intermediate support and consisting of acrylated binder, hardening the protective layer by irradiation with ultraviolet light and removing the intermediate support.
  • the application is preferably done by Lami kidneys at 40 - 80 ° C and under roller pressure.
  • the intermediate carrier can be removed after the UV radiation or at a later time, for example only shortly before use of the electrophotographic recording material.
  • FIGS. 1 to 5 The recording material according to the invention and the method for producing the same are shown schematically by the attached FIGS. 1 to 5.
  • the photoconductive system 2 can in principle be present on the layer support 1 as a single layer, as is indicated in FIG. 1b.
  • Position 3 indicates the protective layer according to the invention, which is located on the intermediate carrier 4 (FIG. 1 a).
  • FIG. 2 indicates the lamination process, for example between two rollers 5, bringing together the electrophotographic recording material 1, 2 and that on the intermediate carrier 4 located protective layer 3 takes place.
  • FIG. 3 shows the irradiation 6 with ultraviolet light of the material provided with the protective layer and intermediate carrier.
  • FIG. 4 shows the removal of the intermediate carrier 4 from the recording material produced according to the invention.
  • FIG. 5 shows electrophotographic recording material produced in accordance with the invention in drum form with an intermediate carrier, which has a tab 7 for pulling off the intermediate carrier 4.
  • Suitable surface-abrasion-resistant, curable acrylated binders for the protective layer 3, which also prevent filming by toner, are, according to the invention, acrylated polymers, for example such modified urethanes, furthermore acrylated polyesters, epoxies and oil-based oligomers.
  • the acrylate functionality justifies the favorable reactivity under UV radiation.
  • Acrylated polyurethanes are particularly characterized by their high resistance to abrasion and chemicals.
  • UV-crosslinking organic prepolymers, in particular reactive resins based on an acrylated polyurethane for example VPS 1748, from Degussa
  • Prepolymers for example acrylated polyesters or epoxides with isocyanates, can also be used as reactive resins.
  • the viscosity values can be significantly reduced in order to achieve protective layers in the thickness range from 0.1 to 10 ⁇ m, preferably 0.1 to 5 ⁇ m.
  • Suitable monomers n- or isobutyl acrylate, 2-ethylhexyl acrylate, N-vinylpyrrolidone, isodecyl acrylate and phenoxyethyl acrylate are suitable as diluents.
  • Formulations with crosslinking agents such as 1,4-butanediol, 1,6-hexanediol diacrylate or especially trimethylolpropane or pentaerythritol tri (tetra) acrylate (TMPTA or PETA) are preferred.
  • Photoinitiators such as benzoin ether derivatives, thioxanthones and their derivatives, and also benzophenones, for example Michler's ketone and acetophenone derivatives, are used to trigger the curing process in ultraviolet light.
  • benzoin ether derivatives thioxanthones and their derivatives
  • benzophenones for example Michler's ketone and acetophenone derivatives
  • Photoinitiators such as benzoin ether derivatives, thioxanthones and their derivatives, and also benzophenones, for example Michler's ketone and acetophenone derivatives, are used to trigger the curing process in ultraviolet light.
  • Benzildimethylketals, 2-hydroxy-2-methyl-1-phenylpropan-1-one, substituted ⁇ -haloacetophenone have proven to be particularly advantageous.
  • Tertiary alkanolamines can be used as additives to the UV hardeners. They improve the resistance of
  • High-pressure mercury lamps for example, are used as the radiation source for the curing process by UV radiation. Those with an electrical output of 100 W / cm lighting length have proven particularly useful.
  • the curable acrylated binders described for the protective layer 3 are outstandingly suitable because of their homogeneous film formation and flexibility, their abrasion behavior, their low toner filming behavior and the possibilities for application. The influence on the photosensitivity of the recording material is slight.
  • All foils and carrier materials transparent to UV light are suitable as intermediate carriers 4.
  • the thickness of the intermediate carrier can vary within wide limits and is not critical. However, it must meet the condition that the intermediate carrier can be easily removed in one piece without tearing, as is indicated in FIG. 4. Accordingly, thicknesses in the range of about 50 to 100 pm are preferred.
  • a preferred embodiment consists in that the protective layer has a thickness of up to approximately 5 ⁇ m a UV-permeable intermediate carrier made of polyester is applied and then laminated onto the photoconductive system in a laminator under pressure and heating to 40 to 80 ° C., preferably to 50 to 60 ° C. and in vacuo.
  • This process can also be designed continuously in an arrangement of the photoconductive system as a double layer in such a way that the layers of the photoconductive system and protective layer are each applied, for example, by flow application and, after drying, the two layers are laminated together under pressure. Curing with ultraviolet light and, if necessary, stripping off the intermediate carrier can follow continuously.
  • a special application of this method for drum coatings is given by covering the inside of a polyester tubular film as an intermediate carrier with the protective layer 3, shrinking this tubular film onto the photoconductor drum and then curing it by means of UV radiation, and then stripping the tubular film as an intermediate carrier or at a later time .
  • the protective layer for UV light is optically transparent.
  • the coherent layer produced on a photoconductive system from organic materials has a uniform thickness of 0.1-10, preferably 0.5-5.0 ⁇ m.
  • the film surface turns out to be smooth, which is necessary for optimal cleaning.
  • the adhesion between the protective layer and the photoconductive system is also high enough to withstand mechanical influences, for example from the cleaning brush to keep.
  • the abrasion and the surface filming are significantly reduced compared to a photoconductor system whose protective layer was applied by coating.
  • the protective layer behaves triboelectrically like the photoconductive system.
  • the protective layer does not stick and no component sweats out of the photoconductive system.
  • the protective layer can also serve to prevent crystallization effects which can arise from contact with the photoconductive surface.
  • the electrical conductivity of the protective layer is such that the chargeability of the photoconductive system is not affected.
  • the materials mentioned allow the protective layer to be electrically permeable, so that charges can flow off from the surface when exposed to light, possibly down to a slight residual voltage.
  • the electrostatic charge image remains completely intact after exposure until image development, which is necessary, since otherwise the resolution of the copy decreases.
  • the specific resistance of the protective layer is not significantly changed by the moisture in the environment.
  • aluminum foil optionally transparent, aluminum-vapor-coated or laminated polyester foil, are used as electrically conductive layer supports, but any other layer support made sufficiently conductive can be used.
  • An insulating intermediate layer can also be provided between the electrically conductive layer support and the photoconductive system.
  • the insulating intermediate layer can be produced by a thermally, anodically or chemically produced aluminum oxide intermediate layer. It can also consist of organic materials. For example, different natural or synthetic resin binders are used that adhere well to a metal or aluminum surface and dissolve little when the other layers are subsequently applied, such as polyamide resins, polyvinylphosphonic acid, polyurethanes, polyester resins or specifically alkali-soluble binders, such as Example styrene-maleic anhydride copolymers.
  • the thickness of such organic intermediate layers can be up to 5 ⁇ m, and that of the aluminum oxide layer is mostly in the range from 0.01 to 1 ⁇ m.
  • the added binder influences both the mechanical behavior such as flexibility, film formation etc. and to a certain extent that electrophotographic behavior such as photosensitivity, residual charge and cyclic behavior.
  • Film-forming compounds such as polyester resins, polyvinyl chloride / polyvinyl acetate copolymers, styrene / maleic anhydride copolymers, polycarbonates, silicone resins, polyurethanes, epoxy resins, acrylates, polyvinyl acetals, polystyrenes, cellulose derivatives such as cellulose acetobutyrates etc. are used as binders.
  • Post-crosslinking binder systems such as DD lacquers, polyisocyanate-crosslinkable acrylate resins, melamine resins, unsaturated polyester resins etc. are also successfully used.
  • additives such as leveling agents such as silicone oils, wetting agents, in particular nonionic substances, plasticizers of different compositions such as Example based on chlorinated hydrocarbons or based on phthalic acid esters. If necessary, sensitizers and / or acceptors can also be added.
  • an electrophotographic recording material consisting of the order of the layers of an electrically conductive substrate made of a 125 ⁇ m thick polyester film, on which a 12 ⁇ m thick layer of aluminum is laminated, an applied 0.2 ⁇ m thick dye layer made of N, N'-dimethylperylimide ( CI 71 130) as a charge-generating layer and an 8 ⁇ m thick charge-transporting layer made from a mixture of 2,5-bis (4'-diethylaminophenyl) -oxdiazole-1,3,4 and cellulose nitrate of standard type 7E according to DIN 53 179 im Weight ratio of 65:35, a UV-curable protective layer is applied.
  • N, N'-dimethylperylimide CI 71 130
  • 8 ⁇ m thick charge-transporting layer made from a mixture of 2,5-bis (4'-diethylaminophenyl) -oxdiazole-1,3,4 and cellulose nitrate of standard type 7E according to DIN 53
  • a polyester film of very good flatness and transparency with a thickness of 75 ⁇ m is used as the carrier with a mixture of 50 parts by weight of an acrylated polyurethane (VPS 1748, Degussa) with a viscosity (25 ° C) of approx.
  • VPS 1748, Degussa an acrylated polyurethane with a viscosity (25 ° C) of approx.
  • the composite is then cured by UV exposure with a high-pressure mercury lamp (100 W / cm) within 15 seconds at a distance of 25 cm on a rotating drum. Thereafter, the carrier serving as the protective layer polyester film is partially stripped and the P hotoekeit and the abrasion resistance measured with and without a protective layer under the same conditions described as follows.
  • Photosensitivity To determine the light discharge curves, the test sample moves on a rotating plate through a charging device to an exposure station, where it is continuously exposed to a xenon lamp. A heat absorption glass and a neutral filter with 15% transparency are connected upstream of the xenon lamp.
  • the light intensity in the measuring plane is in the range of 40 - 60 ⁇ W / cm 2 ; it is measured immediately after determining the light decay curve with an optometer.
  • the charge level (U) and the photo-induced light decay curve are recorded by an electrometer using a transparent probe.
  • the photoconductor layer is characterized by the charge level (U) and the time (T l / 2 ) after which the half te of charging (U o / 2) is reached.
  • the product of T l / 2 and the measured light intensity I ( ⁇ W / cm 2 ) is the half-value energy E l / 2 (uJ / cm 2 ).
  • the residual charge (U R ) after 0.1 sec, determined from the above bright discharge curves, is a further measure of the discharge of the photoconductor layer.
  • Abrasion behavior The abrasion of both materials is measured on a standard abrasion device (Taber Abraser Type 352) under the following conditions:
  • the abrasion in g / m 2 is the quotient of the gravimetrically determined abrasion in mg and the abrasion area.
  • the table also shows values for a recording material 2 which was produced and measured under the same conditions as described, with the difference that the dye was N, N-di (3-methoxypropyl) perylimide.
  • a photoconductive system made of 100 ⁇ m thick aluminum foil as a layer support, a dye layer thereon with N.N'-dimethylperylimide corresponding to a thickness of 0.2 g / m 2 and a charge transport layer made from 50 parts by weight of 2,5-bis (4'-diethylaminophenyl ) -oxdiazole-1,3,4, 25 parts by weight of polyester resin and 25 parts by weight of polyvinyl chloride / polyvinyl acetate copolymer with a thickness of approximately 10 g / m 2 is coated with a UV-curable protective layer with a thickness of 2 ⁇ m.
  • the protective layer is composed of 80 parts by weight of reactive resin, 15 parts by weight of reactive diluent and 5 parts by weight photoinitiator, analogous to that previously Gegan g enes attempt is applied to a plane polyethylene film and this composite laminated on the photoconductive system. It is then cured with UV light under the conditions given in Example 1 and the polyethylene film is removed. The photosensitivity and abrasion behavior are determined in accordance with Example 1.
  • the conditions for applying the protective layer with a thickness of 2-3 ⁇ m, its composition and the determination of photosensitivity and abrasion are the same as described in Example 1.
  • a magnetic brush device with a two-component toner mixture is used for development, for cleaning the Pho on the surface of the remaining toner, the layer is guided past a rotating brush. It shows that under the same copying conditions the copy quality is the same with and without a protective layer.

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  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Photoreceptors In Electrophotography (AREA)
EP82104453A 1981-05-30 1982-05-21 Matériau d'enregistrement électrophotographique et procédé pour sa production Expired EP0066215B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19813121563 DE3121563A1 (de) 1981-05-30 1981-05-30 Elektrophtographisches aufzeichnungsmaterial und verfahren zu seiner herstellung
DE3121563 1981-05-30

Publications (3)

Publication Number Publication Date
EP0066215A2 true EP0066215A2 (fr) 1982-12-08
EP0066215A3 EP0066215A3 (en) 1983-03-16
EP0066215B1 EP0066215B1 (fr) 1986-01-02

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EP82104453A Expired EP0066215B1 (fr) 1981-05-30 1982-05-21 Matériau d'enregistrement électrophotographique et procédé pour sa production

Country Status (5)

Country Link
US (1) US4472491A (fr)
EP (1) EP0066215B1 (fr)
JP (1) JPS57207258A (fr)
AU (1) AU546825B2 (fr)
DE (2) DE3121563A1 (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0157241A1 (fr) * 1984-03-17 1985-10-09 Hoechst Aktiengesellschaft Matériau d'enregistrement photo-sensible et son utilisation dans un procédé pour la production d'une plaque d'impression ou d'un circuit imprimé
EP0353603A2 (fr) * 1988-08-01 1990-02-07 Hughes Aircraft Company Hologramme à feuille mince
EP0564655A1 (fr) * 1991-09-30 1993-10-13 Idemitsu Petrochemical Co. Ltd. Photorecepteur electrophotographique

Families Citing this family (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS58149048A (ja) * 1982-03-02 1983-09-05 Sony Corp 昇華性染料の転写によるカラーハードコピー印画紙の形成方法
JP2595635B2 (ja) * 1988-03-24 1997-04-02 富士電機株式会社 電子写真用感光体
JP2537660B2 (ja) * 1988-05-28 1996-09-25 豊田合成株式会社 合成樹脂製燃料タンクの製造方法
US4921773A (en) * 1988-12-30 1990-05-01 Xerox Corporation Process for preparing an electrophotographic imaging member
US5096796A (en) * 1990-05-31 1992-03-17 Xerox Corporation Blocking and overcoating layers for electroreceptors
US5190608A (en) * 1990-12-27 1993-03-02 Xerox Corporation Laminated belt
US5549999A (en) * 1990-12-27 1996-08-27 Xerox Corporation Process for coating belt seams
US5582949A (en) * 1990-12-27 1996-12-10 Xerox Corporation Process for improving belts
US5501940A (en) * 1993-05-20 1996-03-26 Polaroid Corporation Process for protecting a binary image with a siloxane durable layer that is not removable by hexane, isopropanol or water
US5547534A (en) * 1993-09-09 1996-08-20 Polaroid Corporation Protected image, and process for the production thereof
US5512126A (en) * 1994-03-11 1996-04-30 Polaroid Corporation Optical laminator
CA2269566C (fr) * 1998-04-21 2003-01-21 Nec Corporation Photorecepteur pour l'electrophotographie et methode de fabrication de ce dernier
US6869741B2 (en) 2001-08-29 2005-03-22 Samsung Electronics Co., Ltd. Electrophotographic photoreceptors with novel overcoats
JP4208513B2 (ja) * 2002-07-25 2009-01-14 キヤノン株式会社 画像形成装置
US20070196625A1 (en) * 2006-02-21 2007-08-23 Anderson Daryl E Method and apparatus for secure object labeling

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2651535A1 (de) * 1975-11-11 1977-06-08 Ricoh Kk Elektrophotographischer lichtempfindlicher teil
EP0006356A1 (fr) * 1978-06-16 1980-01-09 EASTMAN KODAK COMPANY (a New Jersey corporation) Support électrophotographique avec une couche protectrice améliorée

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2297691A (en) * 1939-04-04 1942-10-06 Chester F Carlson Electrophotography
JPS5818B2 (ja) * 1977-06-06 1983-01-05 キヤノン株式会社 像保持部材
DE2734288C2 (de) * 1977-07-29 1982-06-03 Hoechst Ag, 6000 Frankfurt Elektrophotographisches Aufzeichnungsmaterial
US4251612A (en) * 1978-05-12 1981-02-17 Xerox Corporation Dielectric overcoated photoresponsive imaging member

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2651535A1 (de) * 1975-11-11 1977-06-08 Ricoh Kk Elektrophotographischer lichtempfindlicher teil
EP0006356A1 (fr) * 1978-06-16 1980-01-09 EASTMAN KODAK COMPANY (a New Jersey corporation) Support électrophotographique avec une couche protectrice améliorée

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0157241A1 (fr) * 1984-03-17 1985-10-09 Hoechst Aktiengesellschaft Matériau d'enregistrement photo-sensible et son utilisation dans un procédé pour la production d'une plaque d'impression ou d'un circuit imprimé
EP0353603A2 (fr) * 1988-08-01 1990-02-07 Hughes Aircraft Company Hologramme à feuille mince
EP0353603A3 (fr) * 1988-08-01 1991-09-25 Hughes Aircraft Company Hologramme à feuille mince
EP0564655A1 (fr) * 1991-09-30 1993-10-13 Idemitsu Petrochemical Co. Ltd. Photorecepteur electrophotographique
EP0564655A4 (fr) * 1991-09-30 1995-06-07 Idemitsu Petrochemical Co

Also Published As

Publication number Publication date
AU8428682A (en) 1982-12-09
JPS57207258A (en) 1982-12-18
DE3121563A1 (de) 1983-02-03
EP0066215B1 (fr) 1986-01-02
US4472491A (en) 1984-09-18
DE3268250D1 (en) 1986-02-13
EP0066215A3 (en) 1983-03-16
AU546825B2 (en) 1985-09-19

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