EP0402260A2 - Elektrophotographisches lichtempfindliches Element - Google Patents

Elektrophotographisches lichtempfindliches Element Download PDF

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Publication number
EP0402260A2
EP0402260A2 EP90401553A EP90401553A EP0402260A2 EP 0402260 A2 EP0402260 A2 EP 0402260A2 EP 90401553 A EP90401553 A EP 90401553A EP 90401553 A EP90401553 A EP 90401553A EP 0402260 A2 EP0402260 A2 EP 0402260A2
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EP
European Patent Office
Prior art keywords
polyether polyol
intermediate layer
photosensitive member
average molecular
layer
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
EP90401553A
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English (en)
French (fr)
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EP0402260A3 (de
EP0402260B1 (de
Inventor
Yuichi C/O Canon K.K. Hashimoto
Takashi C/O Canon K.K. Koyama
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.)
Canon Inc
Original Assignee
Canon Inc
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
Priority claimed from JP14621989A external-priority patent/JP2637557B2/ja
Priority claimed from JP15005889A external-priority patent/JP2608328B2/ja
Application filed by Canon Inc filed Critical Canon Inc
Publication of EP0402260A2 publication Critical patent/EP0402260A2/de
Publication of EP0402260A3 publication Critical patent/EP0402260A3/de
Application granted granted Critical
Publication of EP0402260B1 publication Critical patent/EP0402260B1/de
Anticipated expiration legal-status Critical
Expired - Lifetime 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
    • G03G5/142—Inert intermediate layers

Definitions

  • the present invention relates to an electrophotographic photosensitive member. More particularly, it relates to an electrophotographic photosensitive member comprising an intermediate layer provided between a conductive support and a photosensitive layer.
  • the stabilities at dark portion potential and light portion potential are important in order to form a good image having a constant image density and also free of defects in the course of the repetition of charging and exposure.
  • an intermediate layer having the functions of, e.g., improving the injection of charge from a support to a photosensitive layer, improving the adhesion between a support and a photosensitive layer, and improving coating performance for a photosensitive layer is provided between a support and a photosensitive layer.
  • the so-called function-separated photosensitive member comprising a photosensitive layer having a laminated structure formed of a charge generation layer and a charge transport layer.
  • the charge generation layer is usually provided as a very thin layer with a thickness of, for example, about 0.5 ⁇ m, and its film thickness non-uniformity is closely related with the sensitivity non-uniformity of a photosensitive member.
  • the cause of the film thickness non-uniformity may be named defects, scratches or stains on the surface of a photosensitive member.
  • the intermediate layer is considered to be of very high necessity.
  • a charge generation layer containing a charge-generating material in a high concentration is positioned on an intermediate layer in contact therewith.
  • Such systems can reduce characteristics variations due to temperature and humidity, but are comprised of a resin part having a high resistivity and a powder part having a very high conductivity which are present together. Hence, charge tends to be non-uniformly injected from the support side into a photosensitive layer. This may result in a lowering of potential in the case of the printer of a reverse development system, bringing about the problem that faulty black dots or fogged images tend to be formed.
  • An object of the present invention is to provide an electrophotographic photosensitive member capable of providing potential characteristics and images that are stable to all environmental conditions of from the low temperature and low humidity to the high temperature and high humidity.
  • Another object of the present invention is to provide an electrophotographic photosensitive member that can suppress light portion potential from increasing and dark portion potential from varying even when it is repeatedly used.
  • Still another object of the present invention is to provide en electrophotographic photosensitive member that can provide a defect-free, good image by the formation of an intermediate layer capable of well covering up defects present on a support.
  • an electrophotographic photosensitive member which comprises a conductive support, a photosensitive layer and an intermediate layer interposed therebetween, characterized in that said intermediate layer comprises a material derived from an isocyanate compound and a plurality of kinds of polyether polyol compounds, the polyether polyol compounds meeting at least one of the following requirements i) and ii):
  • the polyether polyurethane used in the present invention is a polymer formed by polymerization or copolymerization of a polyether polyol compound with an isocyanate compound.
  • the polyether polyol compounds used in the present invention may preferably comprise plural kinds of compounds having different weight average molecular weights.
  • Use of the polyether polyol component satisfying this condition makes it possible, in particular, to suppress resistance from increasing under conditions of a low temperature and low humidity, compared with an instance in which a single polyol compound is used, so that a smooth coating film can be formed on a support. It also makes it possible to obtain a sufficient barrier function even under conditions of high temperature and high humidity, so that a decrease in dark portion potential can be made smaller.
  • the polyether polyol compounds in which the ratio of a weight average molecular weight of at least one polyether polyol compound to a weight average molecular weight of at least one polyether polyol compound is in a value of not less than 1.3 is preferred in view of the stability of potential.
  • the polyether polyol compounds used in the present invention may also preferably contain at least one polyether polyol compound having different functionality from that in at least one other polyether polyol.
  • use of the polyether polyol compound satisfying this condition makes the cross-linking of polyurethane chains irregular, so that the flexibility of an intermediate layer coating film can be improved.
  • an increase in resistance of the intermediate layer can be suppressed even under conditions of low temperature and low humidity.
  • the polyether polyol compound used in the present invention includes poly(oxyalkylene) glycols such as poly(oxypropylene) glycol, poly(oxypropylene) poly(oxyethylene) glycol, poly(oxybutylene) glycol, and poly(oxytetramethylene) glycol; poly(oxyalkylene) triols such as poly(oxyethylene) triol, poly(oxypropylene) triol, poly(oxypropylene) poly(oxyethylene) triol, and poly(oxybutylene) triol; and poly(oxyalkylene) polyols such as poly(oxypropylene) polyol and poly(oxypropylene) poly(oxyethylene) polyol formed using ethylene diamine, pentaerythritol, sorbitol, sucrose, starch or the like as an initiator.
  • poly(oxyalkylene) glycols such as poly(oxypropylene) glycol, poly(oxypropylene) poly(oxyethylene) glycol, poly(oxybutylene) glycol,
  • the isocyanate compound used in the present invention includes aromatic isocyanate compounds such as tolylene diisocyanate, methaxylylene diisocyanate, diphenylmethane diisocyanate, and polymethylene polyphenylene isocyanate; hydrogenated products of the above isocyanates; aliphatic isocyanate compounds such as hexamethylene diisocyanate; and block isocyanate compounds in which isocyanate groups of the above isocyanate compound are blocked with a phenol, a ketoxime, an aromatic secondary amine, a tertiary alcohol, an amide, a lactam, a heterocyclic compound or a sulfite.
  • aromatic isocyanate compounds such as tolylene diisocyanate, methaxylylene diisocyanate, diphenylmethane diisocyanate, and polymethylene polyphenylene isocyanate
  • hydrogenated products of the above isocyanates aliphatic isocyanate
  • the above isocyanate compound may also be used in the form of a dimer to a pentamer.
  • a catalyst to accelerate the reaction for producing the polyether polyurethane by polymerization of the above polyether polyol compound with isocyanate compound it is possible to use naphthenates such as cobalt naphthenate, and magnesium naphthenate; tin oxides such as dibutyltin dilaurate, dimethyltin dilaurate, and stannous chloride; and amine compounds such as triethylenediamine, N-methylmorpholine, and N,N,N′,N′-tetramethylpolymethylenediamine.
  • the catalyst may preferably be added in an amount of from 0.001 to 5 % by weight based on the polymer.
  • the isocyanate groups (NCO group) and hydroxy groups (OH group) in a polymer material should be appropriately in a molar ratio of: 1.0 ⁇ NCO group/OH group ⁇ 2.0.
  • a molar ratio lower than 1.0 may make poor the sensitivity of a photosensitive member and also tends to cause a lowering of barrier properties of the intermediate layer under conditions of high temperature and high humidity.
  • a molar ratio larger than 2.0 tends to result in a lowering of adhesion properties of a coating film.
  • At least one polyether polyol compound having a higher weight average molecular weight and at least one other polyether polyol compound having a lower weight average molecular weight may each preferably be in an amount of not less than 20 % by weight, the weight average molecular weight ratio of the higher one to the lower one being 1.3 or more.
  • the compounds having different functionality may each preferaly be in an amount of not less than 5% by weight.
  • the conductive material used in the intermediate layer of the present invention includes metal powders, scaly metal powders and metal short fibers of aluminum, copper, nickel or silver; conductive metal oxides such as antimony oxide, indium oxide, and tin oxide; polymeric conductive materials such as polyvinyl, polyaniline, polythiophene, and polymeric electrolyte; carbon fiber, carbon black, and graphite powder; organic or inorganic electrolytes and metal complexes; and conductive powders whose particle surfaces are coated with any of these conductive materials.
  • the conductive material and the resin may be mixed in a ratio of from about 5:1 to 1:5, and preferably from 4:1 to 1:3. This mixing ratio may be determined taking account of the resistivity, surface properties, coating suitability, etc. of the intermediate layer.
  • the conductive material comprises a powder
  • it may be used in the form of a mixture prepared by a conventional method using a ball mill, a roll mill, a sand mill or the like.
  • a surface active agent, a silane coupling agent, a titanate coupling agent, a silicone oil, a silicone leveling agent and so forth may also be added as other additives.
  • the intermediate layer of the present invention may be formed by a method in which the polymer obtained from a polyol compound and an isocyanate compound and the conductive material are dissolved or dispersed in a suitable solvent, and then the solution or dispersion is coated and dried.
  • it may be formed by a method in which a mixture of a polyol compound and an isocyanate compound which are unreacted or a prepolymer of a polyol compound and isocyanate compound which have been partially reacted is dissolved or dispersed in a suitable solvent together with the conductive material, and thereafter the solution or dispersion is coated and reacted to cure.
  • the thickness of the intermediate layer of the present invention is set taking account of defects such as scratches and dents on the surface of a photosensitive member. It may be commonly set in the range of from about 0.1 to about 50 ⁇ m, and preferably from 1 to 30 ⁇ m.
  • the intermediate layer can be formed by coating methods such as dip coating, spray coating, and roll coating.
  • a second intermediate layer mainly composed of a resin may also be optionally provided on the above intermediate layer for the purpose of, e.g., controlling barrier properties.
  • the resin material used in the second intermediate layer includes polyamides, polyurethanes, polyureas, polyesters, and phenol resins.
  • the second intermediate layer may preferably have a thickness of from 0.1 ⁇ m to 5 ⁇ m, and can be formed by coating in the same manner as in the first-­mentioned intermediate layer.
  • the photosensitive layer may be of either laminated structure functionally separated into a charge generation layer and a charge transport layer, or single layer structure.
  • the charge generation layer can be formed by dispersing an organic charge-generating material including azo pigments such as Sudan Red and Direct Blue, quinone pigments such as pyrenequinone and anthanthrone, quinocyanine pigments, perylene pigments, indigo pigments such as indigo and thioindigo, azulenium salt pigments, and phthalocyanine pigments such as copper phthalocyanine and titanyl oxophthalocyanine, in a binder resin such as polyvinyl formal, polyvinyl butyral, polycarbonate, polystyrene, polyvinyl acetate, acrylic resins, polyvinyl pyrrolidone, ethyl cellulose, or cellulose acetate, and coating the resulting dispersion on the first-mentioned intermediate layer.
  • a charge generation layer may have a film thickness of not more than 5 ⁇ m, and preferably from 0.05 ⁇ m to 2
  • the charge transport layer may be formed using a coating solution obtained by optionally dissolving an organic charge-transporting material including polycyclic aromatic compounds with the structure having biphenylene, anthracene, pyrene, phenanthrene or the like at a main chain or a side chain, nitrogen-­containing cyclic compounds such as indole, carbazole, oxadiazole and pyrazoline, hydrazone compounds, and styryl compounds, in a resin having film-forming properties.
  • an organic charge-transporting material including polycyclic aromatic compounds with the structure having biphenylene, anthracene, pyrene, phenanthrene or the like at a main chain or a side chain, nitrogen-­containing cyclic compounds such as indole, carbazole, oxadiazole and pyrazoline, hydrazone compounds, and styryl compounds, in a resin having film-forming properties.
  • the resin having such film-forming properties includes polyesters, polycarbonate, polymethacrylate, and polystyrene.
  • the charge transport layer may have a thickness of from 5 ⁇ m to 40 ⁇ m, and preferably from 10 ⁇ m to 30 ⁇ m.
  • the photosensitive member of the laminate structure type may have the structure in which the charge generation layer is laminated on the charge transport layer.
  • the photosensitive member of the single layer type it can be formed by incorporating into the resin the charge-generating material and charge-transporting material as described above.
  • a layer of an organic photoconductive polymer such as polyvinyl carbazole or polyvinyl anthracene, a selenium-­deposited layer, a selenium-tellurium-deposited layer, or an amorphous silicone layer may also be used as the photosensitive layer.
  • the conductive support used in the present invention may be comprised of any supports so long as they are conductive, and include, for example, those comprising a metal such as aluminum, copper, molybdenum, chromium, nickel, or brass, molded or formed into drums or sheets, those comprising a plastic film laminated thereon with foil of a metal such as aluminum or copper, those comprising a plastic film on which aluminum, indium oxide, tin oxide or the like has been deposited, or metals, plastic films, papers or the like comprising a conductive layer provided by coating a conductive material alone or together with a suitable binder resin.
  • a metal such as aluminum, copper, molybdenum, chromium, nickel, or brass
  • the electrophotographic photosensitive member of the present invention can be applied generally in electrophotographic apparatus such as copying machines, laser beam printers, LED printers, LCD printers (or liquid crystal shutter printers) and micro-reader printers. It can also be widely used in apparatus for display, recording, personal printing, lithography, facsimile and so forth in which electrophotography is applied.
  • Fig. 1 schematically illustrates an example of the constitution of a transfer electrophotographic apparatus in which a drum photosensitive member according to the present invention is used.
  • the numeral 1 denotes a drum photosensitive member serving as an image supporting member, which is rotated around a shaft 1a at a given peripheral speed in the direction shown by arrow.
  • the photosensitive member 1 is uniformly charged on its periphery, with positive or negative given potential by the operation of a charging means 2, and then photoimagewise exposed to light L (slit exposure, laser beam scanning exposure, etc.) at an exposure area 3 by the operation of an image exposure means (not shown).
  • electrostatic latent images corresponding to the exposure images are successively formed on the periphery of the photosensitive member.
  • the electrostatic latent images thus formed are subsequently developed with toner by the operation of a developing means 4.
  • the resulting toner-­developed images are then successively transferred by the operation of a transfer means 5, to the surface of a transfer medium P fed from a paper feed section (not shown) to the part between the photosensitive member 1 and the transfer means 5 in the manner synchronized with the rotation of the photosensitive member 1.
  • the transfer medium P on which the images have been transferred is separated from the surface of the photosensitive member and led through an image-fixing means 8, where the images are fixed and then delivered to the outside as a transcript (a copy).
  • the surface of the photosensitive member 1 after the transfer of images is subjected to removal of the toner remaining after the transfer, using a cleaning means 6.
  • the photosensitive member is cleaned on its surface and then repeatedly used for the formation of images.
  • the charging means 2 for giving uniform charge on the photosensitive member 1 include corona chargers, which are commonly put into wide use. As the transfer means 5, corona transfer units are also commonly put into wide use.
  • the electrophotographic apparatus may be constituted of a combination of plural components joined as one apparatus unit from among the constituents such as the above photosensitive member, developing means and cleaning means so that the unit can be freely mounted on or detached from the body of the apparatus.
  • the photosensitive member 1 and the cleaning means 6 may be joined into one apparatus unit so that the unit can be freely mounted or detached using a guide means such as a rail provided in the body of the apparatus.
  • the above apparatus unit may be so constituted as to be joined together with the charge means and/or the developing means.
  • optical image exposure to light L is performed by reading of light reflected from, or transmitted through, an original, or the original itself, conversion of the light read to a signal, scanning of a laser beam according to the signal, driving of a light-emitting diode array, driving of a liquid crystal shutter array, etc.
  • Fig. 2 illustrates an example thereof in the form of a block diagram.
  • a controller 11 controls an image reading part 10 and a printer 19. The whole of the controller 11 is controlled by CPU 17. Image data outputted from the image reading part is sent to the other facsimile station through a transmitting circuit. Data received from the other station is sent to a printer 19 through a receiving circuit 12. Given image data are stored in an image memory 16. A printer controller 18 controls the printer 19.
  • the numeral 14 denotes a telephone.
  • An image received from a circuit 15 (image information from a remote terminal connected through the circuit) is demodulated in the receiving circuit 12, and then successively stored in an image memory 16 after the image information is decoded by the CPU 17. Then, when images for at least one page have been stored in the memory 16, the image recording for that page is carried out.
  • the CPU 17 reads out the image information for one page from the memory 16 and sends the decoded image information for one page to the printer controller 18.
  • the CPU 17 receives image information for next page in the course of the recording by the printer.
  • the above coating solution was applied by dip coating to a 60 mm (diameter) x 260 mm aluminum cylinder, followed by drying at 140°C for 30 minutes. A conductive layer with a film thickness of 20 ⁇ m was thus formed.
  • trisazo pigment of the following structural formula 5 parts of polymethyl methacrylate (number average molecular weight: 11,000) and 60 parts of cyclohexanone were dispersed by means of a sand mill in which glass beads of 0.5 mm in diameter were used, and then 120 parts of MEK was added. A dispersion was thus prepared. This dispersion was applied by dip coating to the above intermediate layer, followed by drying at 80°C for 20 minutes. A charge generation layer with a coating weight of 0.15 g/m2 was thus formed.
  • Photosensitive members thus prepared were each fitted to a laser beam printer (LBP-CX, manufactured by Canon Inc.), and electrophotographic performance was evaluated under environmental conditions of normal temperature and normal humidity (23°C, 55 % RH) and also under conditions of high temperature and high humidity (33°C, 90 % RH).
  • LBP-CX laser beam printer
  • Intermediate resin layer (C) Poly(oxypropylene) glycol (hydroxyl value: 267.1 mg ⁇ KOH/g; weight average molecular weight: 420) 1.1 parts Poly(oxypropylene) glycol (hydroxyl value: 133.6 mg ⁇ KOH/g; weight average molecular weight: 840) 2.2 parts Dibutyltin dilaurate 0.02 part MEK 80 parts
  • Intermediate resin layer (E) Poly(oxypropylene) polyol formed using pentaerythritol as an initiator (hydroxyl value: 118.1 mg ⁇ KOH/g; weight average molecular weight: 1,900) 4.8 parts Poly(oxypropylene) polyol formed using pentaerythritol as an initiator (hydroxyl value: 78.7 mg ⁇ KOH/g; weight average molecular weight: 2,850) 9.6 parts Triethylenediamine 0.3 part Isobutyl acetate 100 parts
  • Intermediate resin layer (I) Poly(oxypropylene) triol (hydroxyl value: 70.1 mg ⁇ KOH/g; weight average molecular weight: 2,400) 6.1 parts Poly(oxypropylene) triol (hydroxyl value: 39.0 mg ⁇ KOH/g; weight average molecular weight: 4,320) 9.1 parts Triethylenediamine 0.15 part MEK 100 parts
  • Each of the resulting solutions was applied by dip coating to a conductive support, a 30 mm (diameter) x 260 mm aluminum cylinder, followed by drying at 120°C for 60 minutes. An intermediate layer with a film thickness of 0.8 ⁇ m was thus formed.
  • disazo pigment of the following structural formula 6 parts of polyvinyl butyral resin (degree of butyralation: 70 %; number average molecular weight: 24,000) and 60 parts of cyclohexanone were dispersed by means of a sand mill in which glass beads of 1 mm in diameter were used.
  • 100 parts of methyl ethyl ketone was added, and then the dispersion was applied by dip coating to the above intermediate layer, followed by drying at 100°C for 10 minutes.
  • a charge generation layer with a coating weight of 0.15 g/m2 was thus formed.
  • Photosensitive members thus prepared were each fitted to a small-size copying machine (FC-5, manufactured by Canon Inc.), and electrophotographic performance was evaluated under environmental conditions of normal temperature and normal humidity (23°C, 55 % RH) and also under conditions of high temperature and high humidity (33°C, 90 % RH).
  • the photosensitive member having the intermediate layer (I) of the present invention caused no increase in light portion potential (Vl), and very stable images were obtained.
  • the photosensitive member having the intermediate layer (J) containing the polyol compounds in a ratio of weight average molecular weights of 1:1.2 caused fog because of a serious increase in light portion potential (Vl).
  • the intermediate layers (I) and (J) each had an appearance of a smooth coating film.
  • Intermediate resin layer (M) Poly(oxypropylene) polyol formed using sorbitol as an initiator (hydroxyl value: 623.3 mg ⁇ KOH/g; weight average molecular weight: 360) 2 parts Poly(oxypropylene) polyol formed using sorbitol as an initiator (hydroxyl value: 284.1 mg ⁇ KOH/g; weight average molecular weight: 790) 4 parts Dibutyltin dilaurate 0.02 part MEK 100 parts
  • Example 1 was repeated to prepare photosensitive members, except that the intermediate resin layers were replaced with the following two and the intermediate layer coating solutions were prepared without use of the ketoxime blocked compound of hexamethylene isocyanate.
  • each intermediate layer had a film thickness of 1.1.
  • the charge generation layer had a coating weight of 0.15 g/m2.
  • the charge transport layer had a film thickness of 20 ⁇ m.
  • Intermediate resin layer (Q) Poly(oxypropylene) glycol formed using bisphenol A as initiator (hydroxyl value: 300 mg ⁇ KOH/g) 0.71 parts Tetrafunctional poly(oxypropylene) polyol formed using ethylenediamine as an initiator (hydroxyl value: 760 mg ⁇ KOH/g) 0.28 part Ketoxime blocked compound mainly composed of hexamethylene diisocyanate (effective NCO group: 11.6 % by weight) 1.2 parts Dibutyltin dilaurate 0.01 part
  • Example 8 was repeated to prepare photosensitive members, except for using these coating solutions.
  • Example 8 was repeated to prepare photosensitive members, except for using a coating solution obtained by dissolving each of the above compositions in 100 parts of isobutyl acetate. Evaluation was also made in the same way.
  • the photosensitive member having the intermediate layer (T) caused a serious increase in light portion potential (Vl), bringing about a lowering of image density.
  • Intermediate resin layer (U) Poly(oxypropylene) triol (hydroxyl value: 120 mg ⁇ KOH/g) 2.0 parts Hexafunctional poly(oxypropylene) polyol formed using sorbitol as an initiator (hydroxyl value: 555 mg ⁇ KOH/g) 1.7 parts meta-Xylene diisocyanate 2.0 parts Dibutyltin dilaurate 0.02 part
  • Example 8 was repeated to prepare photosensitive members, except for using these coating solutions. Evaluation was also made in the same way.
  • Intermediate resin layer (W) Tetrafunctional poly(oxypropylene) polyol formed using ethylenediamine as an initiator (hydroxyl value: 510 mg ⁇ KOH/g) 0.5 part Octafunctional poly(oxypropylene) polyol formed using sucrose as an initiator (hydroxyl value: 440 mg ⁇ KOH/g) 2.2 parts meta-Xylene diisocyanate 3.6 parts Dimethyltin dilaurate 0.01 part
  • Example 5 was repeated to prepare photosensitive members, except for using no tolylene diisocyanate.
  • the intermediate layers each had an appearance of a smooth coating film.
  • Example 12 was repeated to prepare a photosensitive member, except for using a coating solution obtained by dissolving the above composition in 100 parts of isobutyl acetate. Evaluation was also made in the same way.

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  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Photoreceptors In Electrophotography (AREA)
EP19900401553 1989-06-08 1990-06-07 Elektrophotographisches lichtempfindliches Element Expired - Lifetime EP0402260B1 (de)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
JP14621989A JP2637557B2 (ja) 1989-06-08 1989-06-08 電子写真感光体
JP146219/89 1989-06-08
JP15005889A JP2608328B2 (ja) 1989-06-12 1989-06-12 電子写真感光体
JP150058/89 1989-06-12

Publications (3)

Publication Number Publication Date
EP0402260A2 true EP0402260A2 (de) 1990-12-12
EP0402260A3 EP0402260A3 (de) 1991-02-06
EP0402260B1 EP0402260B1 (de) 1995-08-23

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EP19900401553 Expired - Lifetime EP0402260B1 (de) 1989-06-08 1990-06-07 Elektrophotographisches lichtempfindliches Element

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EP (1) EP0402260B1 (de)
DE (1) DE69021783T2 (de)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0490622A1 (de) * 1990-12-07 1992-06-17 Canon Kabushiki Kaisha Elektrophotographisches, photoempfindliches Element und Gerät mit einem solchen Element
EP0498626A1 (de) * 1991-02-04 1992-08-12 Canon Kabushiki Kaisha Lichtempfindliches elektrophotographisches Element und Gerät mit einem solchen Element
WO1998050238A1 (de) * 1997-05-03 1998-11-12 Technoplast Beschichtungsgesellschaft Mbh Leitfähige bedruckte bahnen aus kunststoff

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2325676A1 (de) * 1973-05-21 1973-12-06 Ricoh Kk Elektrophotographisches kopiermaterial
JPS62266553A (ja) * 1986-05-14 1987-11-19 Konika Corp 感光体
JPS63187253A (ja) * 1987-01-30 1988-08-02 Canon Inc 電子写真感光体

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2325676A1 (de) * 1973-05-21 1973-12-06 Ricoh Kk Elektrophotographisches kopiermaterial
JPS62266553A (ja) * 1986-05-14 1987-11-19 Konika Corp 感光体
JPS63187253A (ja) * 1987-01-30 1988-08-02 Canon Inc 電子写真感光体

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
PATENT ABSTRACTS OF JAPAN vol. 12, no. 147 (P-698)(2994) 07 May 1988, & JP-A-62 266553 (KONISHIROKU PHOTO IND. CO. LTD.) 19 November 1987, *
PATENT ABSTRACTS OF JAPAN vol. 12, no. 468 (P-797)(3315) 08 December 1988, & JP-A-63 187253 (CANON INC) 02 August 1988, *

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0490622A1 (de) * 1990-12-07 1992-06-17 Canon Kabushiki Kaisha Elektrophotographisches, photoempfindliches Element und Gerät mit einem solchen Element
US5294508A (en) * 1990-12-07 1994-03-15 Canon Kabushiki Kaisha Electrophotographic photosensitive member with polyether polyols-polyisocyanate intermediate layer and apparatus
EP0498626A1 (de) * 1991-02-04 1992-08-12 Canon Kabushiki Kaisha Lichtempfindliches elektrophotographisches Element und Gerät mit einem solchen Element
US5296322A (en) * 1991-02-04 1994-03-22 Canon Kabushiki Kaisha Electrophotographic photosensitive member and apparatus using same
WO1998050238A1 (de) * 1997-05-03 1998-11-12 Technoplast Beschichtungsgesellschaft Mbh Leitfähige bedruckte bahnen aus kunststoff
US6368709B1 (en) 1997-05-03 2002-04-09 Technoplast Beschichtungsgesellschaft Mbh Conductive printed plastic strips
US6720030B2 (en) * 1997-05-03 2004-04-13 Technoplast Beschichtungsgesellschaft Electrically conducting printed webs of plastic

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Publication number Publication date
EP0402260A3 (de) 1991-02-06
DE69021783D1 (de) 1995-09-28
EP0402260B1 (de) 1995-08-23
DE69021783T2 (de) 1996-02-22

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