US3736134A - Humidity resistant photoconductive compositions - Google Patents

Humidity resistant photoconductive compositions Download PDF

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US3736134A
US3736134A US00080567A US3736134DA US3736134A US 3736134 A US3736134 A US 3736134A US 00080567 A US00080567 A US 00080567A US 3736134D A US3736134D A US 3736134DA US 3736134 A US3736134 A US 3736134A
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titanium dioxide
photoconductive
oxide
carboxylic acid
electrographic
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US00080567A
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English (en)
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D W Gosselink
E D Horne
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3M Co
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Minnesota Mining and Manufacturing Co
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    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G5/00—Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
    • G03G5/02—Charge-receiving layers
    • G03G5/04—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
    • G03G5/05—Organic bonding materials; Methods for coating a substrate with a photoconductive layer; Inert supplements for use in photoconductive layers
    • G03G5/0503—Inert supplements
    • G03G5/0507—Inorganic compounds
    • 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
    • G03G5/0503—Inert supplements
    • G03G5/051—Organic non-macromolecular compounds
    • G03G5/0514—Organic non-macromolecular compounds not comprising cyclic groups
    • 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
    • G03G5/08—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being inorganic
    • G03G5/087—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being inorganic and being incorporated in an organic bonding material

Definitions

  • This invention relates to photoconductive compositions and more particularly, to photoconductive compositions having improved humidity resistance.
  • Photoconductive compositions are utilized in numerous electrographic processes both as intermediate and final receptor surfaces for the developer (ink) delineating the subject matter being reproduced.
  • the photoconductive surface must exhibit particular electrical properties depending upon the characteristics of the electrographic process. Humidity can and often does affect these electrical properties to the extent that a photoconductive surface suitable in a particular electrographic process at one humidity may be unsuitable at a different humidity. In general, it is at high relative humidities that the quality of reproduction deeriorates, often to the point that little or no image delination is obtained.
  • This invention relates to a composition and technique for improving humidity resistance at the source by providing an improved humidity resistant photoconductive composition.
  • Exemplary electrographic processes are the electrolytic electrophotographic process described in US. Pat. No. 3,010,883, the electrostatic electrophotographic processes such as is illustrated by US. Pat. No. 3,152,894, and the dynamic electrographic (electropowder) process described in US. application Ser. No. 668,183 and French Pat. No. 1,456,993.
  • the photoconductive composition of this invention has general applicability to electrographic processes operating on the above principles, it is particularly adapted as an intermediate for the production or multiple copies in the electropowder process.
  • a photoconductive sheet is used as a field electrode and is exposed to a light image to create a differentially electronically conductive pattern on the field electrode. While the differentially conductive pattern is present in the photoconductive sheet or field electrode, the surface of the field electrode is uniformly contacted with a conductive applicator containing electrically conductive developer or transfer medium while an electrical field is created by applying a direct current electrical potential between the field electrode and the applicator containing the conductive developer. An electrically conductive path is created between the surface of the field electrode and the applicator. Separation of the developer applicator from the field electrode surface at the end of the development stage is made while the electrical field is maintained.
  • the developer selectively deposits on the field electrode surface in an image-wise manner corresponding to the original light image, thus providing a visible reproduction.
  • No electrostatic pre- 3,736,134 Patented May 29, 1973 charging of the field electrode surface is either indicated or desirable.
  • the developer material may be retained on the field electrode surface or may be transferred to a separate receptor sheet and fixed thereon by chemical or physical means to provide the desired print.
  • a humidity resistant photoconductive sheet consisting essentially of a photoconductor, generally zinc oxide, an emulsifiable polyethylene binder, a water-insoluble fatty acid, and a waterinsoluble dispersant formed from a water-soluble lower alkyl silicone resin.
  • the water-insoluble fatty acids are said to contribute to the water resistance of the final coating.
  • the silicone resins form a water-insensitive coating around the photoconductive zinc oxide particles. It is recognized that silicones in general afford a measure of humidity protection.
  • Titanium dioxide has been found to undergo a gradual decrease in image density with increasing humidity as illustrated by the following data:
  • Image density Temp. F./Rel. humidity (maxi-mum) 72 40% 1.09 O.D.U. /80% 0.76 O.D.U. v80/61% 0.
  • the photoconductive titanium dioxide, inorganic oxide other than titanium dioxide, and carboxylic acid or salt thereof may be combined with a binder in the form of a coating on a substrate suitable for use in an electrographic process.
  • the characteristics of the substrate will depend on the electrographic process in which the photoconductive composition is to be employed. Belts, sheets, rollers, and drums are typical forms of substrates for photoconductive compositions.
  • the photoconductive composition takes the form of a surface coating on a dielectric film to provide an electrographic sheet or field electrode.
  • the electrographic sheet preferably includes an electronically conductive layer bonded to the underside of the dielectric layer, i.e., the face opposing that on which the photoconductive composition is coated.
  • an electrographic sheet 1 having a photoconductive image layer 3, a dielectric layer 5, and conductive layer 7 bonded to the dielectric layer 5.
  • the image layer formed from the photoconductive composition of this invention should upon light exposure provide a differentially conductive pattern wherein the conductive regions are at least twice as conductive as the nonconductive regions, preferably at least 10 times as conductive.
  • the relatively conductive regions of the image layer (containing the conductive pattern) should be as conductive as possible and at least have a maximum resistivity at the surface of 10 ohm-cm., preferably 10 ohm-cm.
  • the relatively nonconductive regions should generally have a minimum resistivity at the surface of 10 ohm-crn., although for special conditions, a resistivity of 10 or 10 ohm-cm. would be suitable.
  • resistivity values are measured under an electric field and for an applied time corresponding to that to be used in the electropowder process, and it is to be remembered that the conductive regions are at least twice as conductive as the nonconductive regions within the above over-all ranges, and the conductive regions are at least about 10 times as conductive as the dielectric layer.
  • the limits of transverse resistivity at the surface of both the nonconductive regions and the conductive regions of the electrode are between about 10" and 10 ohm-cm.
  • the base for the photoconductive surface coating comprises a dielectric layer alone or in combination with a conductive layer bonded to the undersurface of the dielectric layer.
  • the conductivity of the dielectric layer should be about 10 (ohm-cm.)- or lower, and preferably 10" or lower, a conductivity fulfilled by most good dielectric or insulating materials. It is preferred that the dielectric layer exhibit such conductivity independent of the ambient conditions, i.e., temperature and relative humidity. In any case, the conductivity of the dielectric layer should be at most about .1 the conductivity of the conductive layer when present.
  • polyesters such as those available commercially under the trade names Mylar and Scotchpar, polypropylene, polycarbonate, cellulose acetate, and polystyrene. Polyesters are preferred.
  • the conductive layer may be supporting or nonsupporting, for example, a thin vapor coated metal layer or a thicker conductive paper support. Generally, the conductive layer is bonded to the dielectric layer which bears the photoconductive surface layer.
  • the photoconductive composition may be applied directly to a conductive substrate.
  • the conductivity of this layer should be such that no more than a small voltage drop occurs across it when the developing current passes through it. Small in this sense is relative to the voltage drop in other parts of the circuit through which current passes.
  • the voltage drop across the conductive layer should be no more than about 4 of the development voltage.
  • the resistivity of the conductive layer should be less than about ohm-cm., depending upon processing conditions and thickness of the layer.
  • exemplary conductive materials include conductive paper, paper-metal foil laminates and foils, coatings or other forms of metals such as copper, iron, silver, and aluminum.
  • the conductive layer may be in the form of a plurality of plies of conductive material or a single layer made from a single material or a mixture of materials.
  • the titanium dioxide employed in the present invention is photoconductive.
  • the titanium dioxide is of the type described in commonly assigned US. application Ser. No. 867,738 which will enable the production of multiple copies per exposure of the electrographic sheet in the dynamic electrographic process.
  • This titanium dioxide is characterized as having a characteristic relaxation time of less than 9 minutes, and preferably less than 6 minutes. The determination of characteristic relaxation time is fully described in said application Ser. No. 867,738.
  • Employing titanium dioxide exhibiting such a characteristic relaxation time, in combination with the organic acids or salts thereof, has enabled the production of several copies of the original from a single exposure of the electrographic sheet.
  • carboxylic acids which will convert to the metal salt by reaction with the corresponding metal oxide may be employed.
  • carboxylic acids are aliphatic, cycloaliphatic, aromatic acids such as acetic, propionic, butanoic, hexanoic, octanoic, lauric, stearic, benzoic, oleic, cerotic, caproic, linoleic, abietic, rosin acids, dehydroabietic acid, 1- nap th c, Z- Ph AQi q-nitrcbenzc c d m-nitmbeuzoic acid.
  • the carboxylic acids having two or more atoms may be employed, preferably 2 to 30 carbon atoms, and most preferably 6 to 20 carbon atoms.
  • Exemplary salts are ammonium salts and metal salts. Examples of the latter include alkali metal, alkaline earth metal, aluminum, gallium, and zinc salts.
  • Preferred are the zinc salts of the above mentioned carboxylic acids, especially zinc abietate and zinc rosinate.
  • a metal oxide other than photoconductive titanium dioxide suitable metal oxides including barium oxide, calcium oxide, magnesium oxide, lead (II) oxide, lead (IV) oxide, mercuric oxide and zinc oxide.
  • the photoconductive titanium dioxide, carboxylic acid or salt thereof, and metal oxide as described herein may be disposed in an insulating binder, generally an insulating resin binder, to provide a coating for an electrographic sheet.
  • exemplary binders include chlorinated polyethylene, polyvinyl acetate, Lexan polycarbonate, polystyrene, styrene copolymers (e.g., styrene-butadiene copolymer, styrene-n-butyl acrylate copolymer, styrene-isoprene copolymer), acrylonitrile copolymers, polymethyl meth acrylate, polybutyl methacrylate, polyhexyl methacrylate, polydimethylaminoethyl methacrylate, polymethyl acrylate, polycyanoethyl acrylate copolymers, and polyvinylidenechloride polymers.
  • the binders have an acid number below 70, and most preferably below 40, and are free of emulsifying agents.
  • Preferred polymeric binders are polystyrene-butadiene copolymers, chlorinated polyethylene, polyvinyl acetate and Lexan polycarbonate.
  • the photoconductive composition may contain other additives.
  • One preferred additive is a class of materials known as dye sensitizers. Their concentration should preferably be below 3 10* most preferably .3 1'0" grads of dye per gram of titanium dioxide.
  • the carboxylic acid or salt thereof levels of about 185x10 preferably 3.7 l0- equivalents per square meter of titanium dioxide surface have proved suitable.
  • the amount of carboxylic acid or salt thereof may also be expressed in terms of an amount suflicient to provide at least one-half and preferably at least one monomolecular surface coverage of the photoconductive titanium dioxide.
  • the inorganic metal oxide should be present to the extent of at least one-half and preferably at least one chemical equivalent of the carboxylic acid or salt thereof.
  • the amount of inorganic metal oxide may also be expressed as at least .15 by weight based upon the combingd weight of titanium dioxide and inorganic metal oxi e.
  • the titanium dioxide should be present to the extent sufiicient to provide a developable image in the electrographic process. Generally, the titanium dioxide may be present to the extent of about 20 to about volume percent of the combined volume of titanium dioxide and insulating resin binder, preferably 40 to 60 percent, and most preferably 50-55%.
  • EXAMPLES 1-14 A smooth dispersion is prepared by ball milling for 16 hours 38 grams titanium dioxide, 12.6 grams chlorinated polyethylene binder (available under the trade name Tyrin QX 2243.25), ml. toluene, .025 gram of Rhodamine B dissolved in 5 ml. methylene chloride, and 2.85 10- chemical equivalents of the zinc salt of the carboxylic acid (3.7 10- equivalents per meter of titanium oxide), and 2.85 1() chemical equivalents of zinc oxide, as shown in Table 1.
  • Photoconductive copy sheets of each of these compositions are prepared by applying a uniform coating (about .7 mil thick dry) of the dispersion to a 1 mil thick film of polyethylene terephthalate (resistivity of 10 ohms/ square) having a thin vapor deposited aluminum coating (surface resistivity 5 ohms/ square) on the underside and drying at room temperature. These steps are conducted under safelight conditions.
  • the sheets are then processed according to the elec- Rhodamine B dye (0.5% by volume in methylene chloride), carboxylic acid or salt thereof and zinc oxide in the amounts shown in Table 3.
  • the sheets are processed according to the foregoing examples at the temperatures and humidities shown in Table 3, and the image density tropowder process described in US. application Ser. No. 5 values obtained. 668,183.
  • Process conditions are: 1500 volts, development voltage, 30 mil development gap, 15 mil doctor blade TABLE 3 gap, temperature and humidity as shown in Table 1. The L Dmax.
  • developer powder is a thermoplastic, electrically conduc- 10 Eq o tive, magnetically attractable powder ranging from 2-12
  • the electrographic sheets are ex- 23 Abietic acid ,333 ⁇ Q97 000 posed to a tungsten iodide light for the optimum ex- 24 Zincmsmate ⁇ g- X -a L02 L03 posures for each sheet.
  • the level at which the impro vement is seen gm aceette/Zn0 8-3; 8-32 g 8 varies with the composition, as can be observed from a: Z3 l ih ti r telirit ji: 1: 02 0188 ,4 the data.
  • the environmental conditions employed in the g" gm gutyr t n ggg 8- 0 8 8 tests are those which are encountered at various times 6 2 323832 0 0 0 of the year in nearly all countries.
  • the mag- Dispersions are prepared as in the foregoing examples nitude of the improvement increases. containing 38 grams titanium dioxide (characteristic re- Considerations other than humidity resistance may diclaxation time of 1.25 minutes), 12.6 grams of the binder tate limiting the quantity of carboxylic acid or salt and of Example 1, 180 m1. toluene, .025 gram of Rhodamine metal oxide.
  • One factor in particular is the effect of such B in 5 ml. methylene chloride, 2.85 10-3 equivalents 40 additives on light sensitivity.
  • Electrographic sheets 25 traihgitlcxirclgnlvdltcgiiastgamum dioxide available under the Electrographic sheets are prepared in accordance with zTmde name Tyrin (QX 2243-25)- the foregoing examples from 38 g. photoconductive tita- Photoconductive sheets are prepared and tested as in nium dioxide (trade name MSS40-5F), 12.6 g. of chlo- Examples 1-14, the optimum exposure and image density rinated polyethylene binder, 180 ml. toluene, 5 ml. at various conditions being shown in Table 4.
  • a photoconductive composition comprising photoconductive titanium dioxide disposed in an insulating binder, said titanium dioxide being present to the extent Na Quantity 5 of about 20 to about 80 volume percent of the combined Toluene --g-- 6617 volume of titanium dioxide and binder, a first additive Y P Q 7 trade m 521 of a carboxylic acid or metal salt thereof present to the Zinc foslllate Camp, UlllVfiZ extent of at least about 1.85 X equivalents per square trad nartl meter of titanium dioxide surface area, and a second 2 (Natlonal Lead, trade 10 additive of an inorganic metal oxide other than titanium name) g-- 1562 dioxide present to the extent of at least about one-half Rhodamine B -g-- of the equivalents thereof of said carboxylic acid or metal Methanol 9 salt thereof and less than 20% by weight based on the ZIIO trade As Shown 1n combined weight of titanium dioxide and inorganic metal table 5 15 oxide.
  • composition of claim 1 wherein said carboxylic through the homogenizer (Hate name Manton Gau1in acid or metal salt thereof 1s present to the extent of at S15) at 3000 p.s.i.
  • the dispersions thus prepared are alf' aboui equlYalents P Square ⁇ meter of lowed to cool to room temperature before coating titanium dioxide and said inorganic metal oxide other
  • the dispersions are then coated at a wet thickness than titanium oxide is present to the extent of about oneof 3 mils on the polyester Side of aluminum vapor coated half the chemlcal equivalents of said carboxyllc acid or 1 mil polyester film (dry coating thickness approxiately Salt thereof- 07 mil) Drying times of approximately .1 hour are 3.
  • the eleetrographie Sheets are imaged and developed in ficient to provide at least a monomolecular layer thereof the electropowder process at the humidities and temperaon 531d tltamum Q tures shown in Table 5.
  • the conditions for the electro- The composltlon of clam 1 Whemm Said carboxyhc Powder test machine acid or metal salt thereof has from 2 to about carbon atoms.
  • Electrographic sheets are prepared and tested as in Examples 1-14 using the following ingredients:
  • TiO (trade name 540-5K) -Jg-.. 36:1 8.
  • g 12.6 additive is at least one inorganic metal oxide selected from Toluene ml 180 the class consisting of barium oxide, calcium oxide, mag- Rh'odamine B (0.5% by vol. in OH CI .ml 5 nesium oxide, lead (II) oxide, lead (IV) oxide, mer- Zn rosinate As shown in curic oxide, and zinc oxide.
  • a photoconductive composition comprising an in- TABLE 6 Zn rosinate (equiv.lm. I.D. max.
  • T10 Exposure surface (i.e.s.) 72 F./42% so" F./57% 80 F./64% 80 F./76% 80 F./83% 80 F./90%
  • electrographic elements bearing a surface coating of the formulations of this invention are capable of improving both reusability of the elements and imaging life, i.e., the ability to achieve multiple copies per exposure of the electrographic element.
  • titanium dioxide having distributed therein photoconductive titanium dioxide, said titanium dioxide being present to theextent of about 20 to about by volume based on the combined volume of said titanium dioxide and insulating resin binder, a first additive of a carboxylic acid or metal salt the eof presen to the extent of at least about 1.85 X equivalents per square meter of titanium dioxide surface area, and a second additive of an inorganic metal oxide other than titanium dioxide present to the extent of at least about one-half of the equivalents thereof of said carboxylic acid or metal salt thereof and less than 20% by weight based on the combined weight of titanium dioxide and inorganic metal oxide.
  • composition of claim 9 wherein said carboxylic acid or metal salt thereof is present in an amount sufficient to provide at least a monomolecular layer thereof on said titanium dioxide.
  • An electrographic sheet having a surface layer comprising an insulating resin binder having distributed therein photoconductive titanium dioxide, said titanium dioxide being present to the extent of about 20 to about 80% by volume based on the combined volume of said titanium dioxide and insulating resin binder, a first additive of a carboxylic acid or metal salt thereof present to the extent of at least about 1.85 x 10" equivalents per square meter of titanium dioxide surface area, and a second additive of an inorganic metal oxide other than titanium dioxide, said surface layer being bonded to a dielectric layer present to the extent of at least about one-half of the equivalents thereof of said carboxylic acid or metal salt thereof and less than 20% by Weight based on the combined Weight of titanium dioxide and inorganic metal oxide.
  • said inorganic metal oxide is at least one member selected from the class consisting of barium oxide, calcium oxide, magnesium oxide, lead (II) oxide, lead (IV) oxide, mercuric oxide, and zinc oxide.
  • An electrographic sheet having a surface layer comprising an insulating resin binder having distributed there in photoconductive titanium dioxide, said titanium dioxide being present to the extent of about 20 to about 80% by volume based on the combined volume of said titanium dioxide and insulating resin binder, a first additive of a carboxylic acid or metal salt thereof present to the extent of at least about 185x10 equivalents per square meter of titanium dioxide surface area, and a second additive of an inorganic metal oxide other than titanium dioxide present to the extent of at least about one-half of the equivalents thereof of said carboxylic acid or metal salt thereof and less than 20% by weight based on the combined weight of titanium dioxide and inorganic metal oxide, said surface layer being bonded to a dielectric layer and a conductive layer bonded to the underside of said dielectric layer.
  • a photoconductive composition comprising photoconductive titanium dioxide disposed in an insulating binder, said titanium dioxide being itself present to the extent sufficient to provide a developable image in an electrographic process, a first additive of a carboxylic acid or metal salt thereof present to the extent of at least about 1.85 10 equivatents per square meter of titanium dioxide surface areas, and a second additive of an inorganic metal oxide other than titanium dioxide present to the extent of at least about one-half of the equivalents thereof of said carboxylic acid or metal salt thereof and less than 20% by weight based on the combined weight of titanium dioxide and inorganic metal oxide.
  • An electrographic sheet having a surface layer comprising photoconductive titanium dioxide disposed in an insulating resin binder, said titanium dioxide being itself present to the extent sufficient to provide a developable image in an electrographic process, said titanium dioxide being present to the extent of about 20 to about by volume based on the combined volume of said titanium dioxide and [insulating resin binder, a first additive of a carboxylic acid or metal salt thereof present to the extent of at least about 1.85 10- equivalents per square meter of titanium dioxide surface area, and a second additive of an inorganic metal oxide other than titanium dioxide present to the extent of at least about one-half of the equivalents thereof of said carboxylic acid or metal salt thereof and less than 20% by weight based on the combined Weight of titanium dioxide and inorganic metal oxide, said surface layer being bonded to a dielectric layer.

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  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Chemical & Material Sciences (AREA)
  • Inorganic Chemistry (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Photoreceptors In Electrophotography (AREA)
  • Light Receiving Elements (AREA)
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CA (1) CA944205A (enrdf_load_stackoverflow)
CH (1) CH586409A5 (enrdf_load_stackoverflow)
FR (1) FR2111302A5 (enrdf_load_stackoverflow)
GB (1) GB1344679A (enrdf_load_stackoverflow)
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Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3879201A (en) * 1972-12-18 1975-04-22 Xerox Corp Persistent photoconductive compositions
US3912511A (en) * 1970-05-18 1975-10-14 Xerox Corp Multicomponent organic coating of polyester, polyurethane and a humidity barrier thermoplastic resin
US3961954A (en) * 1972-12-27 1976-06-08 Xerox Corporation Acid sensitized charge transfer complexes and cyclic electrostatographic imaging
US4150986A (en) * 1976-09-17 1979-04-24 Ishihara Sangyo Kaisha, Ltd. Doped TiO2 electrophotographic photosensitive materials
US4264696A (en) * 1978-04-27 1981-04-28 Kasei Optonix, Ltd. Electrophotographic photoreceptor
US4282299A (en) * 1977-09-13 1981-08-04 Agfa-Gevaert N.V. Photoconductive recording material containing a zinc oxide particle and a metallic mercapto compound
US4769304A (en) * 1981-04-27 1988-09-06 Fuji Photo Film Co., Ltd. Photoconductive composition and electro-photographic light-sensitive material using said composition
US5612156A (en) * 1988-06-27 1997-03-18 Ishihara Sangyo Kaisha, Ltd. Electrophotographic photosensitive element and a process for manufacturing an offset printing master from the element
EP1205808A1 (en) 2000-11-08 2002-05-15 Ricoh Company, Ltd. Electrophotographic photoreceptor and image forming method and apparatus using the photoreceptor

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2858324B2 (ja) * 1989-08-22 1999-02-17 三菱化学株式会社 電子写真感光体

Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3912511A (en) * 1970-05-18 1975-10-14 Xerox Corp Multicomponent organic coating of polyester, polyurethane and a humidity barrier thermoplastic resin
US3879201A (en) * 1972-12-18 1975-04-22 Xerox Corp Persistent photoconductive compositions
US3961954A (en) * 1972-12-27 1976-06-08 Xerox Corporation Acid sensitized charge transfer complexes and cyclic electrostatographic imaging
US4150986A (en) * 1976-09-17 1979-04-24 Ishihara Sangyo Kaisha, Ltd. Doped TiO2 electrophotographic photosensitive materials
US4282299A (en) * 1977-09-13 1981-08-04 Agfa-Gevaert N.V. Photoconductive recording material containing a zinc oxide particle and a metallic mercapto compound
US4264696A (en) * 1978-04-27 1981-04-28 Kasei Optonix, Ltd. Electrophotographic photoreceptor
US4769304A (en) * 1981-04-27 1988-09-06 Fuji Photo Film Co., Ltd. Photoconductive composition and electro-photographic light-sensitive material using said composition
US5612156A (en) * 1988-06-27 1997-03-18 Ishihara Sangyo Kaisha, Ltd. Electrophotographic photosensitive element and a process for manufacturing an offset printing master from the element
EP1205808A1 (en) 2000-11-08 2002-05-15 Ricoh Company, Ltd. Electrophotographic photoreceptor and image forming method and apparatus using the photoreceptor
US20040126689A1 (en) * 2000-11-08 2004-07-01 Nozomu Tamoto Electrophotographic photoreceptor, and image forming method and apparatus using the photoreceptor
US6790572B2 (en) 2000-11-08 2004-09-14 Ricoh Company Limited Electrophotographic photoreceptor, and image forming method and apparatus using the photoreceptor
US20040197688A1 (en) * 2000-11-08 2004-10-07 Nozomu Tamoto Electrophotographic photoreceptor, and image forming method and apparatus using the photoreceptor
US6858362B2 (en) 2000-11-08 2005-02-22 Ricoh Company, Ltd. Electrophotographic photoreceptor, and image forming method and apparatus using the photoreceptor
US20050100804A1 (en) * 2000-11-08 2005-05-12 Nozomu Tamoto Electrophotographic photoreceptor, and image forming method and apparatus using the photoreceptor
US7282529B2 (en) 2000-11-08 2007-10-16 Ricoh Company Limited Coating liquid for an electrographic photoreceptor and a method of preparation using a ball mill

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JPS5149213B1 (enrdf_load_stackoverflow) 1976-12-25
IT944745B (it) 1973-04-20
CH586409A5 (enrdf_load_stackoverflow) 1977-03-31
GB1344679A (en) 1974-01-23
NL166801C (nl) 1981-09-15
DE2151690A1 (de) 1972-04-20
CA944205A (en) 1974-03-26
NL166801B (nl) 1981-04-15
JPS478485A (enrdf_load_stackoverflow) 1972-05-04
FR2111302A5 (enrdf_load_stackoverflow) 1972-06-02
NL7113612A (enrdf_load_stackoverflow) 1972-04-18
ZA716849B (en) 1972-06-28
DE2151690B2 (de) 1975-10-23
AU3450971A (en) 1973-04-19
AT318390B (de) 1974-10-10

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