EP0000581A2 - Matériau d'enregistrement électrophotographique - Google Patents

Matériau d'enregistrement électrophotographique Download PDF

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Publication number
EP0000581A2
EP0000581A2 EP78100506A EP78100506A EP0000581A2 EP 0000581 A2 EP0000581 A2 EP 0000581A2 EP 78100506 A EP78100506 A EP 78100506A EP 78100506 A EP78100506 A EP 78100506A EP 0000581 A2 EP0000581 A2 EP 0000581A2
Authority
EP
European Patent Office
Prior art keywords
recording material
layer
charge
cellulose
acyl ester
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
EP78100506A
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German (de)
English (en)
Other versions
EP0000581A3 (en
EP0000581B1 (fr
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 EP0000581A2 publication Critical patent/EP0000581A2/fr
Publication of EP0000581A3 publication Critical patent/EP0000581A3/xx
Application granted granted Critical
Publication of EP0000581B1 publication Critical patent/EP0000581B1/fr
Expired legal-status Critical Current

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    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G5/00—Recording-members for original recording by exposure, e.g. to light, to heat or 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 or 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.
  • the invention relates in particular to recording material, the photoconductive layer of which consists of a charge carrier generating layer and a charge transport layer.
  • Photoconductive layers are e.g. B. 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 known.
  • the mechanical properties are disadvantageous when the polyvinylcarbazole used and mainly described is not very flexible as a charge transport layer and, owing to its large molecular weight and its chemical nature, is only slightly compatible or miscible with binders and resins.
  • the adhesion of such layers to the electrically conductive substrate is insufficient for practical purposes.
  • the use of these materials is limited to photoconductor arrangements that are not mechanically resilient.
  • the solution to this problem is based on an electrophotographic recording material comprising an electrically conductive layer support, optionally an insulating intermediate layer and a photoconductive layer comprising at least one charge carrier-generating and charge-transporting layer, binder and conventional additives, and is characterized in that the recording material contains a 75 to 250 ⁇ m thick layer support worked as a photoconductor tape is so flexible that it repeatedly leads over rolls of at least 18 mm in diameter does not tend to hairline cracks and that it contains cellulose acyl esters as a binder an acetyl content of at most 30% and a viscosity above 15 poises, measured according to ASTM D 817-65, formulas A and D 1343-56.
  • the cellulose acyl ester preferably has an acetyl content of at most 15% with a viscosity of over 15, in particular over 50 poises.
  • the acyl groups preferably have two to four carbon atoms.
  • the viscosity is determined in accordance with ASTM D 817-65, formula A and D 1343-56 by dissolving 20 parts by weight of cellulose acyl ester in 8 parts by weight of ethanol (95% by volume) and 72 parts by weight of acetone using the ball drop method at 25 ° C.
  • electrophotographic recording material can be made available which, in comparison with materials with the previously known and customary binders, has the same good photosensitivity and a low residual charge, a great flexibility.
  • a recording material which contains a cellulose acetobutyrate with a maximum of 15% acetyl content and a viscosity in the range of 60-110 poises, measured according to ASTM D 817-65, formulas A and D 1343-56, has proven useful for particularly strong mechanical loads . Repeated guidance takes place via roles e.g. B. in the bending stress test and usually happens 5000 times.
  • the arrangement of a simple photoconductive layer has the advantage of being simple to manufacture (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 advice (FIGS. 2-4).
  • Numeral 1 indicates the electrically conductive layer support
  • number 2 shows the charge-generating layer
  • Number 3 indicates the charge transport layer
  • number 4 indicates the insulating intermediate layer.
  • Section 5 shows layers which represent a charge generation layer in dispersion.
  • dye is represented as a charge carrier generating compound and binder, etc..
  • Aluminum foil or also transparent polyester foil coated with aluminum or aluminum-clad polyester foil with a thickness of S 300 ⁇ m are preferably used as the electrically conductive layer support.
  • the layer support can be a flexible endless belt, e.g. B. made of nickel or steel.
  • a layer support is used which worked as a band, is largely rigid across the direction of travel and is flexible and dimensionally stable along the direction of travel.
  • aluminum-vapor-coated polyester films of sufficient thickness are used, mainly in the range of 75-250 ⁇ m. It has been shown that the greater thickness of this substrate is necessary for the rigidity. Accordingly, a correspondingly greater flexibility of the applied coating is required.
  • straps can be formed with layers as layer supports, which are used in high-speed copying machines.
  • 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.
  • the dyes used or inorganic substances to be mixed such as. B. Tellurium determine the spectral sensitivity of the photoconductive layer to a particular degree.
  • the application of a homogeneous, densely packed dye layer carrier-producing substance 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 evaporated without decomposition under relatively favorable conditions of 10 -3 to 10 -5 Torr and 250 to 400 ° C heating temperature.
  • the temperature of the carrier is below 50 ° C.
  • the production of the charge carrier-producing layer with a uniform thickness can also be achieved by other coating techniques, such as, for example, by mechanically rubbing the finely powdered dye into the electrically conductive layer support, by chemical deposition of a leucase base to be oxidized, by electrolytic or electrochemical processes , by gun spray technique or by applying from a solution and drying the same.
  • other coating techniques such as, for example, by mechanically rubbing the finely powdered dye into the electrically conductive layer support, by chemical deposition of a leucase base to be oxidized, by electrolytic or electrochemical processes , by gun spray technique or by applying from a solution and drying the same.
  • thin layers of inorganic substances which generate charge carriers and are produced by vapor deposition of selenium, doped selenium, cadmium sulfide etc. are also suitable.
  • charge transporting compounds are used as photoconductors. These are mostly organic compounds that are extensive -Electronic system own. These include both monomeric and polymeric aromatic carbocyclic and heterocyclic compounds.
  • Monomers which have at least one dialkylamino group are used in particular.
  • Heterocyclic compounds such as oxdiazole derivatives according to DT-AS 10 58 836, in particular 2,5-bis- (4'-diethylaminophonyl) -oxdiazole-1,3,4, have proven particularly useful.
  • Suitable monomers are, for example, triphenyl amine derivatives, more highly condensed aromatic carbocyclic compounds such as pyrene, benzo-fused heterocycles, and also pyrazoline or imidazole derivatives according to DT-PS 10 60 714 and DT-PS 11 06 599; this subheading also includes triazole, thiadiazole and oxazole derivatives, as are known from German patents 10 60 260, 12 99 296, 11 20 875.
  • polymers z. B more condensed aromatic compounds such as formaldehyde condensation products with various aromatics, such as condensates of formaldehyde and 3-bromopyrene according to DE-OS 21 37 288 particularly proven.
  • 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 photoconductor with a resin binder if the recording material is to be negatively charged. It is preferably transparent.
  • Electrophotographic recording material with these cellulose products as binders gives films with high elasticity.
  • the mixing ratio of the charge transporting compound to the binder can vary.
  • the preferred content of cellulose acyl ester for charge-transporting compound is in the range from 20 to 60 parts by weight to 80 to 40 parts by weight. Too large a proportion of monomers adversely affects flexibility, so that in particularly preferred, flexible forms of stirring, the ratio of cellulose acyl ester to charge-transporting compound is approximately 50:50 parts by weight.
  • the cellulose acyl ester content is in the range below 50%.
  • the charge transport layers with monomers such as 2,5-bis (4'-diethylaminophenyl) oxdiazole-1,3,4 are amorphous according to X-ray goniometer measurements.
  • 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 / um, preferably 0.005 to 1 / um and in the range of 2 to 20 / m, preferably 3 to 10 / um are suitable. If the charge-generating layer is in dispersion, layer thicknesses in the range of preferably 0.1-1 ⁇ m are suitable.
  • Leveling agents such as silicone oils, wetting agents, in particular nonionic substances, plasticizers of different compositions, such as, for example, those based on chlorinated hydrocarbons or based on phthalic acid esters are considered to be conventional 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.
  • Beäampfte aluminum on a polyester film of 75 / um thickness is the pigment N, N'-dimethyl-3,4,9,10-tetracarboxylic perylene in fun Vakuumbedamp- g sstrom at 10 -4 - 10 -5 Torr within Evaporated at about 230 ° C for 2 minutes.
  • the distance between the despair 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 electrically conductive substrate. is completely covered by this.
  • the respective layer thickness is 9-10 / um.
  • a charge transport layer is applied over it, which consists of equal parts by weight of 2,5-bis (4'-diethyl-. Aminophenyl) oxydiazole-1,3,4 and the respective cellulose acetobutyrate.
  • the layers applied from tetrahydrofuran solutions have layer weights in the range of 7-9 g / m 2 .
  • a charge transport layer composition comprising 50 parts by weight of photoconductor, 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 in accordance with Example 1 and subjected to the bending stress test.
  • a layer thickness 9-10 g / m 2
  • a dye layer in accordance with Example 1 and subjected to the bending stress test.
  • no, on the 125 m thick isolated short hair cracks and on the 190 um thick polyester film very strong and long hair cracks / / contact at 25 mm roller diameter and 5000 rounds in the photoconductive layer on polyester film of 75 / um thickness at all on.
  • occasional hairline cracks occur with a roller diameter of 18 mm and a carrier thickness of 75 ⁇ m.
  • a condensation product of 3-bromopyrene and formaldehyde in accordance with DT-OS 21 37 288 is used as a polymer charge-transport compound.
  • Example 1 Using the dye according to Example 1 gives a negative charge of 630 volts E 1/2 to 4.9 / uJ / cm 2 .
  • a polynuclear chincn as a dye Hostapermscharlach GO, CI 59 300
  • a cellulose acetobutyrate with a viscosity of about 75 poises and an acetyl group content of 13.5% a photosensitivity with negative charging to 430 volts becomes E 1/2 4.7 / uJ / cm 2 measured.
  • Example 1 On a dye layer, as described in Example 1, a solution of 50 parts by weight of 2,5-bis- (4'-diethylaminophenyl) oxdiazole-1,3,4 together with 40 parts by weight of a cellulose acetobutyrate with 13.5% acetyl groups and one Viscosity of about 75 poises and 10 parts by weight of a cellulose acetate with an acetyl group content of about 40% and a viscosity of 40 poises applied and dried to a layer thickness of 8-9 / um.

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  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Photoreceptors In Electrophotography (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
EP78100506A 1977-07-29 1978-07-26 Matériau d'enregistrement électrophotographique Expired EP0000581B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE2734289A DE2734289C2 (de) 1977-07-29 1977-07-29 Photoleiterband
DE2734289 1977-07-29

Publications (3)

Publication Number Publication Date
EP0000581A2 true EP0000581A2 (fr) 1979-02-07
EP0000581A3 EP0000581A3 (en) 1979-02-21
EP0000581B1 EP0000581B1 (fr) 1981-06-17

Family

ID=6015173

Family Applications (1)

Application Number Title Priority Date Filing Date
EP78100506A Expired EP0000581B1 (fr) 1977-07-29 1978-07-26 Matériau d'enregistrement électrophotographique

Country Status (5)

Country Link
US (1) US4224395A (fr)
EP (1) EP0000581B1 (fr)
JP (1) JPS5426742A (fr)
AU (1) AU519787B2 (fr)
DE (2) DE2734289C2 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5609001A (en) * 1992-03-09 1997-03-11 Enthalpy S.A. Modular insulating upholstery for closed chamber

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4584253A (en) * 1984-12-24 1986-04-22 Xerox Corporation Electrophotographic imaging system
JP4032353B2 (ja) * 2003-12-26 2008-01-16 セイコーエプソン株式会社 回路基板の製造方法、回路基板、電子機器、および電気光学装置
JP5718791B2 (ja) * 2011-11-08 2015-05-13 富士フイルム株式会社 電子写真感光体およびこれを用いた複写機、その感光層形成用ドープ

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2327808A (en) * 1941-08-08 1943-08-24 Eastman Kodak Co Photographic emulsion for spraying upon surfaces and its application
US2748022A (en) * 1952-08-08 1956-05-29 Eastman Kodak Co Cellulose ester photographic emulsions
US3155503A (en) * 1959-02-26 1964-11-03 Gevaert Photo Prod Nv Electrophotographic material
DE1278242B (de) * 1961-12-30 1968-09-19 Gevaert Photo Prod Nv Elektrophotographisches Aufzeichnungsmaterial
BE617032A (fr) * 1961-04-29
US3146688A (en) * 1961-05-01 1964-09-01 Xerox Corp Xerographic machine
US3331687A (en) * 1962-09-24 1967-07-18 Render Belipa G M B H Fa Electrophotographic material
US3652268A (en) * 1970-03-16 1972-03-28 Dick Co Ab Barrier coated electrophotographic sheet suitable for liquid development
BE763389A (fr) * 1971-02-24 1971-08-24 Xerox Corp Nouvelle plaque xerographique contenant des pigments photoinjecteurs dequinones polynucleaires,
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

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5609001A (en) * 1992-03-09 1997-03-11 Enthalpy S.A. Modular insulating upholstery for closed chamber

Also Published As

Publication number Publication date
DE2734289C2 (de) 1982-06-09
US4224395A (en) 1980-09-23
EP0000581A3 (en) 1979-02-21
AU519787B2 (en) 1981-12-24
DE2860771D1 (en) 1981-09-24
JPH0139097B2 (fr) 1989-08-18
JPS5426742A (en) 1979-02-28
EP0000581B1 (fr) 1981-06-17
DE2734289A1 (de) 1979-02-01
AU3772378A (en) 1980-01-10

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