EP0046959B2 - Elektrophotographisches Aufzeichnungsmaterial - Google Patents

Elektrophotographisches Aufzeichnungsmaterial Download PDF

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Publication number
EP0046959B2
EP0046959B2 EP81106554A EP81106554A EP0046959B2 EP 0046959 B2 EP0046959 B2 EP 0046959B2 EP 81106554 A EP81106554 A EP 81106554A EP 81106554 A EP81106554 A EP 81106554A EP 0046959 B2 EP0046959 B2 EP 0046959B2
Authority
EP
European Patent Office
Prior art keywords
layer
recording material
binder
polyisocyanate
hydroxyl groups
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.)
Expired - Lifetime
Application number
EP81106554A
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German (de)
English (en)
French (fr)
Other versions
EP0046959A3 (en
EP0046959B1 (de
EP0046959A2 (de
Inventor
Wolfgang Dr. 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
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Filing date
Publication date
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Application filed by Hoechst AG filed Critical Hoechst AG
Publication of EP0046959A2 publication Critical patent/EP0046959A2/de
Publication of EP0046959A3 publication Critical patent/EP0046959A3/de
Application granted granted Critical
Publication of EP0046959B1 publication Critical patent/EP0046959B1/de
Publication of EP0046959B2 publication Critical patent/EP0046959B2/de
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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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
    • G03G5/14—Inert intermediate or cover layers for charge-receiving layers
    • G03G5/147—Cover layers
    • G03G5/14708—Cover layers comprising organic material
    • G03G5/14713—Macromolecular material
    • G03G5/14747—Macromolecular material obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • G03G5/14769—Other polycondensates comprising nitrogen atoms with or without oxygen atoms in the main chain
    • 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
    • G03G5/14708—Cover layers comprising organic material
    • G03G5/14713—Macromolecular material
    • G03G5/14717—Macromolecular material obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • G03G5/14734—Polymers comprising at least one carboxyl radical, e.g. polyacrylic acid, polycrotonic acid, polymaleic acid; Derivatives thereof, e.g. their esters, salts, anhydrides, nitriles, amides
    • 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
    • G03G5/14708—Cover layers comprising organic material
    • G03G5/14713—Macromolecular material
    • G03G5/14747—Macromolecular material obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • G03G5/14752—Polyesters
    • 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
    • G03G5/14708—Cover layers comprising organic material
    • G03G5/14713—Macromolecular material
    • G03G5/14747—Macromolecular material obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • G03G5/14756—Polycarbonates
    • 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
    • G03G5/14708—Cover layers comprising organic material
    • G03G5/14713—Macromolecular material
    • G03G5/14747—Macromolecular material obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • G03G5/1476—Other polycondensates comprising oxygen atoms in the main chain; Phenol resins
    • 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
    • G03G5/14708—Cover layers comprising organic material
    • G03G5/14713—Macromolecular material
    • G03G5/14791—Macromolecular compounds characterised by their structure, e.g. block polymers, reticulated polymers, or by their chemical properties, e.g. by molecular weight or acidity

Definitions

  • the invention relates to an electrophotographic recording material composed of an electrically conductive layer support, optionally an insulating intermediate layer and a photoconductive layer system consisting of organic materials consisting of a layer optionally containing a binder with a charge-generating compound and a layer with charge-transporting compound which has a monomeric aromatic or heterocyclic compound is at least one dialkylamino group or two alkoxy groups, and a protective transparent cover layer in a thickness of 0.5 to 10 pm.
  • Photoconductive layer comprising at least one layer with a charge-generating and charge-transporting compound
  • highly sensitive, organic photoconductor layers (DE-B-23 14 051) are used on conductive carrier films or tapes due to their high elasticity.
  • very highly sensitive photoconductor systems according to, for example, DE-A-27 34 288 can be used as endless belts because of their great flexibility, which can be guided over deflecting rollers with a relatively small diameter.
  • cover layers on mono- or multiple photoconductor layers with inorganic or preferably organic photoconductor consist of a very specific combination of crosslinking agent with crosslinkable polymer or copolymer in a weight ratio of 1 to 9 .
  • crosslinking agents e.g. Prepolymers containing melamine formaldehyde and imino groups and, as crosslinkable polymers, those which have ⁇ , ⁇ -ethylenically unsaturated carboxylic acid or partial ester configurations. From this it can be seen that only these agents provide the physical properties which are essential and advantageous for a cover layer on a photoconductive layer.
  • the photoconductive multilayer is three layers of different thicknesses of different organic material. A top layer is applied to this, which is 20 pm thick and normally more than about 10 pm thick.
  • an electrophotographic recording material mentioned in claim 1 which is characterized in that the top layer consists of a surface abrasion-resistant organic binder made of phenoxy resin, purely acrylic resin, preferably of an aqueous dispersion of polyisocyanate and hydroxyl group-containing polyester or ether Polyisocyanate and hydroxyl group-containing acrylic or epoxy resin, or of polyisocyanate prepolymer or polyisocyanates with temporarily blocked isocyanate groups and that the top layer is 0.5 to 15.5 ⁇ m thick.
  • the top layer consists of a surface abrasion-resistant organic binder made of phenoxy resin, purely acrylic resin, preferably of an aqueous dispersion of polyisocyanate and hydroxyl group-containing polyester or ether Polyisocyanate and hydroxyl group-containing acrylic or epoxy resin, or of polyisocyanate prepolymer or polyisocyanates with temporarily blocked isocyanate groups and that the top layer is 0.5 to 15.5 ⁇ m thick.
  • electrophotographic recording materials can be made available which, with almost the same photosensitivity, significantly improve the abrasion resistance and the service life.
  • the abrasion-resistant top layer can be applied by coating, dipping or also (electrostatic) spraying with subsequent drying and optionally hardening.
  • the multi-layer arrangements can be used more profitably not only on flexible conductive substrates, but also on drums.
  • the photoconductive layer can be in the form of a single layer, as indicated in position 6 in FIG. 1. It can also be in the form of a double-layer arrangement which consists of a layer 2 containing charge carrier-producing compounds, as shown in FIGS. 2 and 3, and a layer containing charge-transporting compounds under the respective position 3, which is generally preferred .
  • the conductive layer support is indicated with 1 in each case.
  • An insulating intermediate layer is indicated at position 4.
  • Position 5 shows a layer of charge generating compounds in dispersion.
  • Position 7 indicates the protective cover layer according to the invention.
  • aluminum foil optionally transparent, aluminum vapor-coated or laminated polyester foil, is used as the conductive layer support, but any other layer support made sufficiently conductive can be used.
  • 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 pm, that of the aluminum oxide layer is largely in the range of 0.01-1 pm.
  • Chem. Soc. Japan 25,411-413 / 1952 can be prepared from perylene-3,4,9,10-tetracarboxylic anhydride and o-phenylenediamine or 1,8-diaminophthalene, according to DE-A-2 314 051.
  • Dyes according to DE-A-2 246 255, 2 353 639 and 2 356 370 can also be used, for example.
  • the application of a homogeneous, densely packed layer 2 is preferably obtained by vacuum deposition.
  • An advantageous layer thickness range of layer 2 is between 0.005 and 3 ⁇ m, since the adhesive strength and homogeneity of the vapor-deposited compound are particularly favorable here.
  • homogeneous, well-covering dye layers with thicknesses of the order of 0.1-3 ⁇ m can also be obtained by grinding the dye with a binder, in particular with highly viscous cellulose nitrates and / or crosslinking binder systems, for example polyisocyanate crosslinkable systems Acrylic resins, lacquers based on polyisocyanates and hydroxyl-containing polyester or ether, and by subsequently applying these dye dispersions 5 to the layer support, as can be seen from FIG. 4.
  • Compounds which have an extensive n-electron system are particularly suitable as the charge transport material in layers 3 and 6. These include, in particular, monomeric aromatic or heterocyclic compounds, such as those which have at least one dialkylamino group or two alkoxy groups.
  • Oxdiazole derivatives which are mentioned in German Patent 1,058,836, have proven particularly useful. These include in particular 2,5-bis (p-diethylaminophenyl) oxidiazole-1,3,4.
  • Suitable monomeric electron donor compounds are, for example, triphenylamine derivatives, more highly condensed aromatic compounds such as pyrene, benzo-condensed heterocycles, and also pyrazoline or imidazole derivatives (DE-B-10 60 714, 11 06 599), which also include triazole, thiadiazole and especially oxazole derivatives, for example 2-phenyl-4- (2-chlorophenyl) -5- (4-diethylamino) oxazole, as are disclosed in German patents 1,060,260,1,299,296,120,875.
  • the charge transport layer 3 has practically no photosensitivity in the visible range (420-750 nm). It preferably consists of a mixture of an electron donor compound with a resin binder if negative charging is to be carried out.
  • Layer 3 is preferably transparent. However, it is also possible that it does not need to be transparent, for example in the case of a transparent, conductive layer support. It has a high electrical resistance ( ⁇ 10120) and prevents the discharge of electrostatic charge in the dark. When exposed, it transports the charges generated in the organic dye layer.
  • the added binder influences both the mechanical behavior such as abrasion, flexibility, film formation etc. and to a certain extent the 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 (for example Desmophen / Desmodur @ , Bayer AG), polyisocyanate-crosslinkable acrylate resins, melamine resins, unsaturated polyester resins etc. are also successfully used.
  • the mixing ratio of the charge transporting compound to the binder can vary. However, the requirement for maximum photosensitivity, i.e. the largest possible proportion of charge-transporting compound and after crystallization to be avoided and increase in flexibility, i.e. as large a proportion of binders as possible, relatively certain limits.
  • a mixing ratio of about 1: 1 parts by weight has generally been found to be preferred, but ratios between 4: 1 to 1: 2 are also suitable.
  • the thicknesses of layers 3 and 6 are preferably between about 3 and 20 pm.
  • Leveling agents such as silicone oils, wetting agents, in particular nonionic substances, are the usual additives.
  • micronized organic powders of up to approximately 30% by weight, preferably 10% by weight, have also proven to be advantageous. To a certain extent, this improves the abrasion resistance and significantly improves the rougher, matt surface, in particular the adhesion promoter for the subsequent top layer.
  • Preferred organic powders can be: micronized polypropylene waxes, polyethylene waxes, polyamide waxes or polytetrafluoroethylene and polyvinylidene fluoride powders.
  • Both non-crosslinking and postcrosslinking and self-crosslinking binders are suitable as surface abrasion-resistant organic binders for the top layer.
  • Phenoxy resin is mentioned as the non-crosslinking, organic binder.
  • Suitable postcrosslinking binders are: two-component systems made from crosslinking with aliphatic and / or aromatic polyisocyanate resin. Hydroxyl group-containing, saturated or unsaturated polyisocyanate resin-crosslinking, hydroxyl group-containing, saturated or unsaturated polyester or ether or polyisocyanate-crosslinking hydroxyl group-containing acrylic or epoxy resins, one-component systems made of air-drying polyurethane resin (polyurethane alkyd resin), or temporarily blocked isocyanate-curing polyisocyanates with er -Groups.
  • Pure acrylic resins preferably aqueous dispersions, are suitable as self-crosslinking, optionally thermosetting binders.
  • the cover layer consists of a self-crosslinking polyisocyanate and the photoconductive layer contains a compound with hydroxyl groups.
  • the organic binders mentioned for the protective cover layer 7 are outstandingly suitable because of their homogeneous film formation and flexibility, their abrasion behavior and the application possibilities. The influence on the photosensitivity of the recording material is negligible.
  • the protective cover layer is optically transparent in a thin arrangement.
  • the continuous layer produced on an organic photoconductor system in a double layer arrangement has a uniform thickness of about 0.5-10 ⁇ m, preferably of 0.5-5.0 ⁇ m.
  • the film surface turns out to be smooth, which is necessary for optimal cleaning.
  • the adhesion between the cover layer and the photoconductor system is also high enough to withstand mechanical influences, for example from the cleaning brush.
  • the abrasion is significantly improved compared to the photoconductor system to be coated. It is essential that the cover layer behaves triboelectrically like the photoconductor layer. At 40 ⁇ 50 ° C as the storage temperature, the cover layer does not stick and no component exudes from the photoconductor layer.
  • the cover layer also serves to prevent crystallization effects which can arise from contact with the photoconductor surface.
  • the electrical conductivity of the cover layer is low enough not to influence the charge acceptance of the photoconductor.
  • the materials mentioned allow the cover 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 until after exposure completely preserved for image development, which is necessary, otherwise the resolution of the copy decreases.
  • the specific electrical resistance is not changed by moisture in the environment.
  • the film surface is free of hydrophilic components so that the surface resistance is not changed by the climate.
  • the preferred application systems are coatings on a coating machine, preferably by means of flow application on, for example, photoconductor tapes, and spray technologies, optionally also electrostatically for applying the top layer on drums.
  • a coating machine preferably by means of flow application on, for example, photoconductor tapes, and spray technologies, optionally also electrostatically for applying the top layer on drums.
  • a particular embodiment of the recording material according to the invention consists in dispersing additives of micronized organic powders in the photoconductive layer; this significantly improves adhesion and abrasion properties.
  • photoconductive layers are coated with, for example, hydroxyl-containing binders, in particular with cellulose esters such as cellulose nitrates, with a polyfunctional aromatic / aliphatic polyisocyanate or polyisocyanate prepolymer, thereby producing an adhesion-promoting transition zone of curing between the photoconductive layer / cover layer.
  • hydroxyl-containing binders in particular with cellulose esters such as cellulose nitrates
  • a polyfunctional aromatic / aliphatic polyisocyanate or polyisocyanate prepolymer thereby producing an adhesion-promoting transition zone of curing between the photoconductive layer / cover layer.
  • the residual charge (U R ) after 0.1 sec, determined from the above bright discharge curves, is a further measure of the discharge of a photoconductor layer.
  • the abrasion of both materials is measured on a standard abrasion device (Taber Abrasser 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 thickness of this protective cover layer is about 0.5 pm after drying; with constant photosensitivity, the applied, glossy layer improves abrasion and increases the fatigue strength.
  • a photoconductive system produced in accordance with Example 2 is tested in a dry toner copier with regard to its surface properties and its photosensitivity.
  • a magnetic brush device with a two-component toner mixture is used for development; the layer is guided past a rotating brush to clean the residual toner from the photoconductor surface. It shows that under the same copying conditions the copy quality is the same with and without the top layer.
  • strong surface films are already visible on the photoconductor layer without a protective cover layer and the surface is matte, on the other hand only minor surface films are visible on one with a cover layer and the surface is still shiny.
  • micronized polyethylene wax (PE) or micronized polytetrafluoroethylene (PTEE) can also be dispersed into a charge transport layer composed of 65 parts of To and 35 parts of cellulose nitrate.
  • PE polyethylene wax
  • PTEE micronized polytetrafluoroethylene
  • Photosensitivity and abrasion are determined according to the information in Example 1.
  • micronized powder additives especially in combination with cover layers, result in a significant reduction in abrasion.

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  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • General Physics & Mathematics (AREA)
  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Photoreceptors In Electrophotography (AREA)
EP81106554A 1980-08-30 1981-08-24 Elektrophotographisches Aufzeichnungsmaterial Expired - Lifetime EP0046959B2 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19803032774 DE3032774A1 (de) 1980-08-30 1980-08-30 Elektrophotographisches aufzeichnungsmaterial
DE3032774 1980-08-30

Publications (4)

Publication Number Publication Date
EP0046959A2 EP0046959A2 (de) 1982-03-10
EP0046959A3 EP0046959A3 (en) 1982-07-28
EP0046959B1 EP0046959B1 (de) 1985-10-02
EP0046959B2 true EP0046959B2 (de) 1990-12-19

Family

ID=6110782

Family Applications (1)

Application Number Title Priority Date Filing Date
EP81106554A Expired - Lifetime EP0046959B2 (de) 1980-08-30 1981-08-24 Elektrophotographisches Aufzeichnungsmaterial

Country Status (5)

Country Link
US (1) US4390609A (enrdf_load_stackoverflow)
EP (1) EP0046959B2 (enrdf_load_stackoverflow)
JP (1) JPS5789764A (enrdf_load_stackoverflow)
AU (1) AU540031B2 (enrdf_load_stackoverflow)
DE (2) DE3032774A1 (enrdf_load_stackoverflow)

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JPS5337430A (en) * 1976-09-20 1978-04-06 Canon Inc Electrophotographic light sensitive element
JPS543538A (en) * 1977-06-10 1979-01-11 Canon Inc Electrophotographic photoreceptor
US4251612A (en) * 1978-05-12 1981-02-17 Xerox Corporation Dielectric overcoated photoresponsive imaging member

Also Published As

Publication number Publication date
JPS5789764A (en) 1982-06-04
EP0046959A3 (en) 1982-07-28
AU540031B2 (en) 1984-10-25
DE3172532D1 (en) 1985-11-07
EP0046959B1 (de) 1985-10-02
EP0046959A2 (de) 1982-03-10
DE3032774A1 (de) 1982-05-06
JPH0363064B2 (enrdf_load_stackoverflow) 1991-09-27
US4390609A (en) 1983-06-28
AU7426581A (en) 1982-03-11

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