EP0000582B1 - Elektrophotographisches Aufzeichnungsmaterial - Google Patents

Elektrophotographisches Aufzeichnungsmaterial Download PDF

Info

Publication number
EP0000582B1
EP0000582B1 EP78100507A EP78100507A EP0000582B1 EP 0000582 B1 EP0000582 B1 EP 0000582B1 EP 78100507 A EP78100507 A EP 78100507A EP 78100507 A EP78100507 A EP 78100507A EP 0000582 B1 EP0000582 B1 EP 0000582B1
Authority
EP
European Patent Office
Prior art keywords
layer
recording material
charge
weight
parts
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
Application number
EP78100507A
Other languages
German (de)
English (en)
French (fr)
Other versions
EP0000582A3 (en
EP0000582A2 (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
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 EP0000582A2 publication Critical patent/EP0000582A2/de
Publication of EP0000582A3 publication Critical patent/EP0000582A3/xx
Application granted granted Critical
Publication of EP0000582B1 publication Critical patent/EP0000582B1/de
Expired legal-status Critical Current

Links

Images

Classifications

    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G5/00—Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
    • G03G5/02—Charge-receiving layers
    • G03G5/04—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
    • G03G5/05—Organic bonding materials; Methods for coating a substrate with a photoconductive layer; Inert supplements for use in photoconductive layers
    • G03G5/0528—Macromolecular bonding materials
    • G03G5/0557—Macromolecular bonding materials obtained otherwise than by reactions only involving carbon-to-carbon unsatured bonds
    • G03G5/0585—Cellulose and derivatives
    • 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
    • G03G5/10—Bases for charge-receiving or other layers
    • G03G5/102—Bases for charge-receiving or other layers consisting of or comprising metals

Definitions

  • the invention relates to electrophotographic recording material comprising an electrically conductive layer support, optionally an insulating intermediate layer and a photoconductive layer comprising at least one charge carrier-producing and charge-transporting layer, binder and conventional additive-containing layer.
  • it relates to a recording material with a charge generation layer and charge transport layer.
  • Photoconductive layers are e.g. known from German Offenlegungsschriften 21 08 935, 21 08 938, 21 08 944, 21 08 958, 21 08 968, 21 08 984 and 21 08 992.
  • the mechanical properties are disadvantageous in that the polyvinylcarbazole used and mainly described in the form of a charge transport layer is not very flexible and, because of its large molecular weight and its chemical nature, is only slightly compatible or miscible with binders and resins.
  • the adhesion of such layer systems to the electrically conductive substrate is insufficient for practical purposes. The use of these materials is therefore limited to photoconductive arrangements that are not mechanically resilient.
  • an electrophotographic recording material comprising an electrically conductive layer support, optionally an insulating intermediate layer and a photoconductive layer with a charge-generating compound and charge-transporting compound, binder and conventional additives or a photoconductive layer consisting of a layer optionally containing a binder with charge carrier Compound and a layer with charge-transporting compound, binder and conventional additives and is characterized in that the recording material is worked with a 75 to 250, thick layer support as a photoconductor tape, and that it contains a cellulose nitrate as a binder, which has a viscosity of 400 ⁇ 25 cPoises at concentrations between 4 and 12 percent in 5% aqueous acetone according to DIN 53 179 (standard type 4-12), preferably between 4 and 9 percent (standard type 4-9).
  • electrophotographic recording material can be made available which, compared to materials with the previously known and customary binders and with great flexibility, has significantly improved photosensitivity and an extraordinarily low residual charge, both with continuous exposure and particularly with flash exposure.
  • the materials according to the invention allow the materials according to the invention to be used for mechanically strong photoconductor tapes which run in a relatively fast cyclic copying process, especially under flash exposure.
  • the recording material is repeatedly passed over rollers and tested in a bending stress test, usually 5000 times.
  • the photoconductive layer of the recording material according to the invention can be present in a single layer or as a photoconductive system in a multilayer.
  • the arrangement of the photoconductive layer in a simple layer has the advantage of a simpler method of manufacture in itself (FIG. 1).
  • the arrangement in separate charge carrier generating layer and charge transport layer has the advantage of the compact arrangement of the particles and the optimal charge carrier generation rate (FIGS. 2-4).
  • cellulose nitrates are often mentioned with the list of further cellulose esters and ethers (cf. US Pat. No. 3,152,895, column 2, lines 46 to 48; US Pat. No. 3 652 268, column 4, line 34; GB - A - 944 941, page 2, lines 104/105; CH - A - 564 797, column 2, lines 26 to 28).
  • the exceptional special position of cellulose nitrates in terms of flexibility and photo sensitivity properties is completely surprising.
  • Number 1 indicates the electrically conductive layer support
  • number 2 shows the charge generation layer
  • number 3 indicates the charge transport layer
  • number 4 indicates the adhesion-improving intermediate layer.
  • Section 5 shows layers which represent a charge generation layer in dispersion.
  • Numeral 6 shows a photoconductive layer consisting of charge-transporting compound, charge carrier-producing compound and binder, etc.
  • Aluminum foil preferably also transparent, aluminum-vapor-coated polyester foil or aluminum-clad polyester foil with a thickness of up to 300 ⁇ m, is preferably used as the electrically conductive layer carrier, but any other sufficiently conductive carrier material can also be used.
  • the layer support is a flexible endless belt and can also consist of nickel or steel etc. According to the invention, a layer support is used which is largely rigid transversely to the direction of travel and is flexible and dimensionally stable along the direction of travel. In addition to a band made of metal, which already fulfills these conditions very well at thicknesses of 100-200 ⁇ m, aluminum-vapor-coated polyester films of sufficient thickness are used, mainly in the range of 75-250 ⁇ m.
  • straps can be formed with layers as a layer carrier, which are necessary for use in high-speed copying machines.
  • the insulating intermediate layer 4 can consist of organic material or optionally also a thermally, anodically or chemically produced aluminum oxide intermediate layer, and in addition to promoting adhesion, it has the aim, for example, of reducing the charge carrier injection from the layer carrier into the photoconductive layer in the dark by its arrangement. On the other hand, it does not hinder the flow of charge during the exposure process.
  • Natural or synthetic resin binders can be used for the intermediate layer, such as, for example, polyamide resins, polyvinylphosphonic acid, polyurethanes or polyester resins. Its thickness can be up to 5 ⁇ m, while thicknesses of aluminum oxide layers mostly range from 0.01-1 ⁇ m.
  • Such inorganic or organic substances are used as charge-generating compounds, as have been known for this purpose up to now.
  • This subheading includes dyes or amorphous selenium e.g. in the form of vapor deposition layers.
  • the dyes used or inorganic substances to be mixed, e.g. Tellurium particularly determine the spectral sensitivity of the photoconductive layer.
  • the application of a homogeneous, densely packed dye layer as a charge carrier generating layer is known and is obtained by evaporating the dye onto the carrier in vacuo.
  • the dyes can be vaporized without decomposition under relatively favorable conditions (10- 3- 10- 5 Torr, 250-400 ° C heating temperature).
  • the temperature of the carrier is below 50 ° C.
  • An advantageous layer thickness range of the evaporated dye is between 0.005 and 2 ⁇ m, but is particularly preferred between 0.005 and 1 ⁇ m, since the adhesive strength and homogeneity of the evaporated dye are particularly favorable here.
  • the production of the charge carrier-producing layer with a uniform thickness can also be achieved by other coating techniques, for example by mechanically rubbing the finely powdered material into the electrically conductive layer carrier, by chemical deposition of a leuco base to be oxidized, by electrolytic or electrochemical processes or also by gun spray technique or by applying from a solution and drying the same.
  • homogeneous, well covering dye layers with thicknesses of the order of 0.1-3 ⁇ m by thickness are also possible by dispersing the dyes in a binder according to the invention and by coating the electrically conductive substrate (Layer 5 in Fig. 4).
  • the use of highly viscous cellulose nitrates is particularly advantageous, because during grinding a very good distribution of the pigments (small grain size) is achieved during the coating.
  • the ratio of charge generating substance to binder can vary within wide limits. Pre-coatings with a dye content of over 50% and a correspondingly high optical density are preferred. This achieves the use of dyes which are less thermally stable, such as azo or bisazo dyes, and which at the same time have an adhesion-promoting effect.
  • charge-transporting compounds are used as the photoconductor. These are primarily organic compounds that have an extensive n-electron system. These include both monomeric and polymeric aromatic or heterocyclic compounds.
  • the monomers used are in particular those which have at least one dialkylamino group or two alkoxy groups.
  • Heterocyclic compounds such as oxdiazole derivatives according to DE - B - 10 58 836, such as 2,5-bis (4'-diethylaminophenyl) oxdiazole-1,3,4, have proven particularly useful.
  • Suitable monomers are, for example, triphenylamine derivatives, more highly condensed aromatic compounds such as pyrene, benzo-fused heterocycles, and also pyrazoline or imidazole derivatives according to DE-C-10 60 714 and DE-C-11 06 599; this subheading also includes triazole, thiadiazole and oxazole derivatives, as are known from German patents 1060260, 12 99 296, 11 20 875.
  • Formaldehyde condensation products with various aromatics such as, for example, condensates of formaldehyde and 3-bromopyrene in accordance with DE-A-21 37 288 have proven themselves as polymers.
  • the charge transport layer has practically no photosensitivity in the visible range of approximately 420-750 nm. It preferably consists of a mixture of an electron donor compound as a charge-transporting compound in a mixture with a resin binder if the recording material is to be negatively charged. It is preferably transparent, but this is not necessarily the case if the electrically conductive substrate is transparent.
  • the charge transport layer has a high electrical resistance and prevents the discharge of electrostatic charge in the dark. When exposed, it transports the generated charges, whereby it is assumed that the polar (charged) excited state of the donor molecule is reduced and / or non-polar ground state is increased due to the increased polarity of the binder (electron-attracting nitro groups in the cellulose nitrate).
  • the added binder influences both the mechanical behavior, such as abrasion, flexibility, film formation, etc., and the electrophotographic properties, such as photosensitivity, residual charge, etc.
  • film-forming compounds such as polyester resins, polyvinyl chloride / polyvinyl acetate, have been used as binders.
  • Copolymers, styrene-maleic anhydride copolymers, silicone resins, reactive resins, DD lacquers, polycarbonates and acrylates or methacrylates etc. are used.
  • the viscosity is determined in Ubbelohde viscometers with different capillaries 1-111 at 25 ° C and a solids concentration of 10% (DIN 51 562). Then the viscosity of the binder batches in tetrahydrofuran is well above 50 cSt.
  • the mixing ratio of the charge transporting compound to the binder can vary.
  • Films with a high proportion of cellulose nitrates can also only be charged to a low degree on a conductive support; by adding charge-transporting compounds, however, charging can be done Gradually improve and stabilize with increasing content, ie dark discharge is reduced.
  • the preferred content of cellulose nitrate to charge transporting compound ranges from 20 to 60 parts by weight to 40 to 80 parts by weight. Too large a proportion of monomers adversely affects flexibility, so that in particularly preferred, flexible embodiments the ratio of cellulose nitrate to charge-transporting compound is between 30 to 50 parts by weight to 50 to 70 parts by weight.
  • the cellulose nitrate content lies in the lower range indicated.
  • the transport layers with monomers from charge-transporting compounds are amorphous according to X-ray goniometer measurements.
  • the respective requirements of the recording material according to the invention for use in a copying machine can be met within a wide range by different adjustment of the photoconductive layer with regard to the viscosity of the cellulose nitrate and with regard to the proportion of the charge-transporting compound.
  • the layer thickness of the photoconductive layer is in a range which corresponds to a layer weight of approximately 5 to 50 g / m 2 .
  • layer thicknesses in the range from 0.005 to 2 ⁇ m, preferably 0.005 to 1 ⁇ m or in the range from 2 to 20 ⁇ m, preferably 3 to 10 ⁇ m are suitable.
  • layer thicknesses in the range from 0.01 to 3 ⁇ m, preferably 0.1 to 1 ⁇ m, are suitable.
  • the specified limits can be extended upwards or downwards on a case-by-case basis.
  • Leveling agents such as silicone oils, wetting agents, in particular nonionic substances, plasticizers of different compositions, such as, for example, based on chlorinated hydrocarbons or based on phthalic acid esters are added to the photoconductive layer as customary additives. If necessary, sensitizers and / or acceptors can also be added to the charge transport layer, but only to the extent that the optical transparency of the charge transport layer is not significantly impaired.
  • the pigment dye N, N'-dimethyl-perylene-3,4,9,10-tetracarboxylic acid diimide is placed on an aluminum-vapor-coated polyester film of 75 .mu.m thick in a vacuum evaporation system at 10- 4- 10- 5 Torr within 2 minutes at approx . Evaporated at 280 ° C.
  • the distance between the evaporator source and the substrate is about 20 cm.
  • the homogeneously evaporated dye layer has a layer weight in the range of 100-200 mg / m 2 , the carrier being completely covered.
  • the cellulose nitrates are collodion wool, which are phlegmatized with 35 parts by weight of n-butanol or water.
  • the cover layer contains about 60 parts by weight of photoconductor TO and 40 parts by weight of cellulose nitrate.
  • the layer thickness is approx. 10 ⁇ m.
  • a high-viscosity, ester-soluble and a low-viscosity, alcohol-soluble collodion wool were used.
  • the photosensitivity is determined to:
  • a series of transport layers with differently viscous cellulose nitrates is applied to aluminum-vapor-coated polyester of 75 ⁇ m thickness with a dye layer vapor-deposited thereon as indicated in Example 1 under comparable conditions in 8-10 ⁇ m thickness.
  • the composition of the dried layers is a uniform 60 parts TO and 40 parts of the respective cellulose nitrate, which differs in its degree of viscosity and extends over a standard type range from 15 to 4 according to DIN 53 179.
  • a dye layer is applied to polyester film 75, 125 and 190 ⁇ m thick, made conductive by means of an evaporated aluminum layer, in accordance with Example 1.
  • a charge transport layer consisting of 65 parts by weight of TO and 35 parts by weight of highly viscous cellulose nitrate is applied in a layer thickness range of 7.0-9.5 g / m 2 in a uniform manner by coating and drying under the same conditions.
  • the material is either glued or welded into a loop and subjected to a bending stress test.
  • the flexible loop is often guided over roller diameters of different thicknesses. It is run 5000 times at a constant speed of rotation via a rubber drive roller of approx. 80 mm 0 and a replaceable steel roller with a diameter of 12, 18 or 25 mm as standard.
  • a rubber drive roller of approx. 80 mm 0
  • a replaceable steel roller with a diameter of 12, 18 or 25 mm as standard.
  • the photoconductor layer is exposed to an increased bending stress, so that hairline cracks can occur on the surface under this stress. This formation of hairline cracks is advantageously observed in the dark under oblique angles.
  • a charge transport layer composition comprising 50 parts by weight of TO, 25 parts by weight of polyester resin and 25 parts by weight of vinyl chloride / vinyl acetate copolymer is applied in a layer thickness of 9-10 g / m 2 to a dye layer according to Example 1 and subjected to the bending stress test. Thereafter, at 25 mm roller diameter and 5000 revolutions, none at all in the photoconductive layer on polyester film 75 ⁇ m thick, short hairline cracks with 125 ⁇ m thick and very strong and long hairline cracks on the 190 ⁇ m thick polyester film. In addition, with a roller diameter of 18 mm and a carrier thickness of 75, hairline cracks already occur.
  • Example 1 As indicated in Example 1, the following dyes and selenium are applied to aluminum-coated polyester film 75 ⁇ m thick in a layer thickness range of 100-200 mg / m 2 .
  • Coating and drying (except for the selenium layer, which was dried for 3 minutes at 85 ° C) is carried out under comparable conditions (see Example 1), the thickness of the charge transport layer is 8-10 ⁇ m, the TO / binder weight ratio is 1: 1.
  • Example 1 The measurement conditions of Example 1 also apply, the light intensity (xenon XBO 150) of one measurement series being approximately 150 ⁇ W / cm 2 , another 80-85 ⁇ W / cm 2 and a charging range of 600-700 V being aimed for.
  • the residual charge is determined, which is established after 0.1 seconds.
  • a condensation product of 3-bromopyrene and formaldehyde produced according to DT-A-21 37 288 has proven itself well as a polymeric, charge-transporting compound.
  • the sensitivity can be significantly improved compared to known binders such as polyester resin.
  • a charge transport layer composed of 80 parts by weight of bromopyrene resin and 20 parts by weight of low-viscosity cellulose nitrate in a thickness of 6-7 ⁇ m is applied to a material coated in accordance with Example 1.
  • an analog material with a charge transport layer is produced from 80 parts by weight of bromopyrene resin and 20 parts by weight of polyester resin in a thickness of 6-7 ⁇ m.
  • the sensitivity measurement gives the following values:
  • a charge transport layer composed of equal parts by weight TO and high-viscosity and low-viscosity cellulose nitrate in a layer thickness of 9-10 g / m 2 is applied to 100 ⁇ m thick polyester film (optical quality).
  • the dye layer is evaporated according to Example 1 and then a charge transport layer composed of 65 parts by weight of TO and 35 parts by weight of highly viscous cellulose nitrate with a layer thickness of 8.1 g / m 2 ( 6.3 ⁇ m) layered and dried.
  • the material is checked for its dark discharge and flash sensitivity.
  • the dark decay of a photoconductor sample is measured in a Dyntest-90 device (paper analyzer) from ECE, G corden.
  • a measuring probe registers the charge (U o ) or the voltage drop ( ⁇ D ), which is recorded by a recorder. The voltage drop in the dark after 2 seconds is measured in the charging area of interest:
  • the discharge behavior during flash exposure is determined by mounting the sample on an aluminum plate, charging it and introducing it into the measuring station.
  • the photoconductor layer is exposed through a transparent charge probe using a xenon short-arc lamp (Strobotac 1538-A flash lamp, General Radio).
  • the charges measured with the charge probe are amplified and registered with a recorder.
  • Wavelength and light energy can be varied using interference and gray filters that can be inserted into the beam path. If the energy of the flash unit is sufficiently constant, the light energy is determined directly after removing the photoconductor sample from the beam path (UDT-80 X optometer, see also Example 1).
  • the sample After reaching a constant set charge the sample is exposed to a defined flash energy (constant flash duration 3 ⁇ s) and the remaining charge is determined after 1 second.
  • the residual charge U (V) is drawn as a function of the flash light energy E ( ⁇ J / cm 2 ) in Fig. 6 (curve 1).
  • the half-value energy (E 1/2 ) at which the photoconductor layer has discharged up to half the initial charge can be determined from these curves.
  • Tetrahydrofuran solutions with different TO contents in high-viscosity cellulose nitrate are spun onto a dye-coated material as described in Example 1.
  • the resulting layer thicknesses correspond to approximately 7-8 g / M 2 .
  • the measurement is carried out analogously to the measurement method given in Example 1 (light intensity approx. 90 uW / cm 2 , Xenon XBO 150):
  • a batch of equal parts by weight of desensitized, highly viscous cellulose nitrate and a perinone dye (C.I. 71 105) in tetrahydrofuran is intensively ground for 2 hours. After dispersing, the solution is diluted fourfold and the approximately 1% coating solution is coated on aluminum-vaporized 75 ⁇ m thick polyester film and dried.
  • the layer thickness of this pigment pre-coat corresponds to 255 and 50 mg / m 2 after drying, the composition pigment / cellulose nitrate 60/40.
  • a charge transport layer composed of 65 parts by weight of TO and 35 parts by weight of highly viscous cellulose nitrate is applied uniformly to the pigment precursors of different thicknesses with a layer weight of approximately 8 g / m 2 and dried.
  • the sensitivity is determined analogously to Example 1 (light intensity approx. 85 ⁇ W / cm 2 ; Xenon XBO 150).
  • a pigment precoat composed of 2 parts by weight of a polynuclear quinone (CI 59 300) and one part by weight of phlegmatized, highly viscous cellulose nitrate is dispersed analogously to Example 11 and precoated in a suitable layer in a different layer thickness.
  • a layer corresponding to a layer weight of approximately 7 g / m 2 and a composition of 90 parts by weight TO and 30 parts by weight low-viscosity cellulose nitrate is layered thereon.
  • a condensation product from the reaction of perylene-3,4,9,10-tetracarboxylic anhydride and o-phenylenediamine according to DT-A-23 14 051 is evaporated analogously to Example 1 on 190 ⁇ m thick aluminum-vapor-coated polyester film.
  • the layer weight of the homogeneous, blue-violet dye layer is 195 mg / m 2.
  • Layers of 65 parts by weight of TO and 35 parts by weight of cellulose nitrate (highly viscous) are layered on top.
  • a layer made for comparison with a vinyl chloride / vinyl acetate copolymer (PVC / PVAc) provides a relatively insensitive system on the same dye vapor deposition layer.
  • the photosensitivity is measured analogously to Example 1 (light intensity: 90 ⁇ W / cm 2 ; Xenon XBO 50):

Landscapes

  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Photoreceptors In Electrophotography (AREA)
EP78100507A 1977-07-29 1978-07-26 Elektrophotographisches Aufzeichnungsmaterial Expired EP0000582B1 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE2734288 1977-07-29
DE2734288A DE2734288C2 (de) 1977-07-29 1977-07-29 Elektrophotographisches Aufzeichnungsmaterial

Publications (3)

Publication Number Publication Date
EP0000582A2 EP0000582A2 (de) 1979-02-07
EP0000582A3 EP0000582A3 (en) 1979-02-21
EP0000582B1 true EP0000582B1 (de) 1981-06-17

Family

ID=6015172

Family Applications (1)

Application Number Title Priority Date Filing Date
EP78100507A Expired EP0000582B1 (de) 1977-07-29 1978-07-26 Elektrophotographisches Aufzeichnungsmaterial

Country Status (5)

Country Link
US (1) US4220697A (enrdf_load_stackoverflow)
EP (1) EP0000582B1 (enrdf_load_stackoverflow)
JP (1) JPS5426741A (enrdf_load_stackoverflow)
AU (1) AU516489B2 (enrdf_load_stackoverflow)
DE (2) DE2734288C2 (enrdf_load_stackoverflow)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5660443A (en) * 1979-10-23 1981-05-25 Copyer Co Ltd Lamination type electrophotographic receptor
JPS57152790U (enrdf_load_stackoverflow) * 1981-03-20 1982-09-25
DE3121563A1 (de) * 1981-05-30 1983-02-03 Hoechst Ag, 6000 Frankfurt Elektrophtographisches aufzeichnungsmaterial und verfahren zu seiner herstellung
JPS58152247A (ja) * 1982-03-05 1983-09-09 Mita Ind Co Ltd 電子写真用有機感光体
JPS61173486A (ja) * 1985-01-25 1986-08-05 三京冷暖株式会社 電気カ−ペツト等における発熱体の製法
DE3537979A1 (de) * 1985-10-25 1987-04-30 Hoechst Ag Elektrophotographisches aufzeichnungsmaterial
US5283144A (en) * 1992-09-02 1994-02-01 Xerox Corporation Purified photogenerating pigments
DE69524044T2 (de) 1994-12-22 2002-07-04 Ciba Speciality Chemicals Holding Inc., Basel Elektrophotographischer Photorezeptor
US5965670A (en) * 1997-12-24 1999-10-12 Ppg Industries Ohio, Inc. Curable-film forming compositions having improved mar and acid etch resistance
US6493063B1 (en) * 1999-06-24 2002-12-10 Advanced Micro Devices, Inc. Critical dimension control improvement method for step and scan photolithography

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3121006A (en) * 1957-06-26 1964-02-11 Xerox Corp Photo-active member for xerography
GB944941A (enrdf_load_stackoverflow) * 1958-11-17 1900-01-01
US3146688A (en) * 1961-05-01 1964-09-01 Xerox Corp Xerographic machine
US3152895A (en) * 1962-03-14 1964-10-13 T F Washburn Company Coating composition for the production of electrophotographic recording members
US3447957A (en) * 1964-08-19 1969-06-03 Xerox Corp Method of making a smooth surfaced adhesive binder xerographic plate
US3652268A (en) * 1970-03-16 1972-03-28 Dick Co Ab Barrier coated electrophotographic sheet suitable for liquid development
JPS4856434A (enrdf_load_stackoverflow) * 1971-11-16 1973-08-08
CH564797A5 (en) * 1971-11-16 1975-07-31 Gen Co Ltd Electrostatic recording carrier - for writing or printing
DE2242595C2 (de) * 1972-08-30 1982-06-09 Hoechst Ag, 6000 Frankfurt Elektrophotographisches Aufzeichnungsmaterial
DE2220408C3 (de) * 1972-04-26 1978-10-26 Hoechst Ag, 6000 Frankfurt Elektrophotographisches Aufzeichnungsmaterial und Verfahren zu seiner Herstellung

Also Published As

Publication number Publication date
DE2734288A1 (de) 1979-02-01
DE2734288C2 (de) 1982-06-03
AU516489B2 (en) 1981-06-04
JPS5426741A (en) 1979-02-28
EP0000582A3 (en) 1979-02-21
JPH0139096B2 (enrdf_load_stackoverflow) 1989-08-18
DE2860772D1 (en) 1981-09-24
EP0000582A2 (de) 1979-02-07
US4220697A (en) 1980-09-02
AU3772478A (en) 1980-01-10

Similar Documents

Publication Publication Date Title
EP0046959B2 (de) Elektrophotographisches Aufzeichnungsmaterial
DE2353639C2 (de) Elektrophotographisches Aufzeichnungsmaterial
DE3046240C2 (enrdf_load_stackoverflow)
DE2737516C3 (de) Elektrophotographisches Aufzeichnungsmaterial
EP0061089B1 (de) Elektrophotographisches Aufzeichnungsmaterial
DE3526249A1 (de) Elektrophotographisches aufzeichnungsmaterial
DE2037450B2 (de) Verfahren zur Herstellung eines elektrofotografischen Aufzeichnungsmaterials
EP0000582B1 (de) Elektrophotographisches Aufzeichnungsmaterial
DE2241406A1 (de) Elektrophotographisches aufzeichnungsmaterial
DE3026653A1 (de) Elektrophotographisches element
DE2810466C2 (de) Elektrofotografisches Aufzeichnungsmaterial
EP0040402B1 (de) Elektrophotographisches Aufzeichnungsmaterial
EP0000581B1 (de) Elektrophotographisches Aufzeichnungsmaterial
EP0113437B1 (de) Elektrophotographisches Aufzeichnungsmaterial
DE2237679A1 (de) Elektrophotographisches aufzeichnungsmaterial
DE3236477A1 (de) Elektrophotographisches aufzeichnungsmaterial
DE2822762C2 (de) Elektrophotographisches Aufzeichnungsmaterial
DE3040047C2 (de) Elektrophotografisches Aufzeichnungsmaterial
EP0220604B1 (de) Elektrophotographisches Aufzeichnungsmaterial
DE2744171C2 (de) Elektrofotografisches Aufzeichungsmaterial
DE10160279A1 (de) Verfahren zur Herstellung eines lichtempfindlichen Baukörpers für die Elektrophotographie
DE2059540B2 (de) Elektrophotographisches Aufzeichnungsmaterial mit einer photoleitfänigen Schicht
EP0218981B1 (de) Elektrophotographisches Aufzeichnungsmaterial
EP0231835B1 (de) Elektrophotographisches Aufzeichnungsmaterial
DE2747144C3 (de) Elektrofotografisches Aufzeichnungsmaterial

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

PUAL Search report despatched

Free format text: ORIGINAL CODE: 0009013

AK Designated contracting states

Designated state(s): DE FR GB NL

AK Designated contracting states

Designated state(s): DE FR GB NL

17P Request for examination filed
GRAA (expected) grant

Free format text: ORIGINAL CODE: 0009210

AK Designated contracting states

Designated state(s): DE FR GB NL

REF Corresponds to:

Ref document number: 2860772

Country of ref document: DE

Date of ref document: 19810924

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: FR

Payment date: 19920611

Year of fee payment: 15

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: GB

Payment date: 19920615

Year of fee payment: 15

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: NL

Payment date: 19920731

Year of fee payment: 15

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: DE

Payment date: 19920921

Year of fee payment: 15

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: GB

Effective date: 19930726

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: NL

Effective date: 19940201

NLV4 Nl: lapsed or anulled due to non-payment of the annual fee
GBPC Gb: european patent ceased through non-payment of renewal fee

Effective date: 19930726

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: FR

Effective date: 19940331

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: DE

Effective date: 19940401

REG Reference to a national code

Ref country code: FR

Ref legal event code: ST

PLBE No opposition filed within time limit

Free format text: ORIGINAL CODE: 0009261

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: NO OPPOSITION FILED WITHIN TIME LIMIT