EP0004944A2 - Matériau pour enregistrement électrophotographique - Google Patents

Matériau pour enregistrement électrophotographique Download PDF

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Publication number
EP0004944A2
EP0004944A2 EP79101123A EP79101123A EP0004944A2 EP 0004944 A2 EP0004944 A2 EP 0004944A2 EP 79101123 A EP79101123 A EP 79101123A EP 79101123 A EP79101123 A EP 79101123A EP 0004944 A2 EP0004944 A2 EP 0004944A2
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EP
European Patent Office
Prior art keywords
dye
yellow
recording material
photoconductive layer
mixture
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
EP79101123A
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German (de)
English (en)
Other versions
EP0004944B1 (fr
EP0004944A3 (en
Inventor
Erwin Dr. Lind
Franz Freimuth
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Hoechst AG
Original Assignee
Hoechst AG
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Publication date
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Application filed by Hoechst AG filed Critical Hoechst AG
Publication of EP0004944A2 publication Critical patent/EP0004944A2/fr
Publication of EP0004944A3 publication Critical patent/EP0004944A3/xx
Application granted granted Critical
Publication of EP0004944B1 publication Critical patent/EP0004944B1/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, 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
    • G03G5/09—Sensitisors or activators, e.g. dyestuffs

Definitions

  • the present invention relates to an electrophotographic recording material composed of an electrically conductive layer support, in particular suitable for the production of printing forms or printed circuits, and a panchromatically sensitized photoconductive layer composed of organic photoconductor, binder, sensitizing dye and conventional additives.
  • an electrophotographic recording material which is panchromatically sensitized, easy to produce and easy to handle and, with uniformly good sensitivity over the entire visible spectral range, enables the production of excellent reproductions.
  • an electrophotographic recording material comprising an electrically conductive layer support and a panchromatically sensitized photoconductive layer composed of organic photoconductor, binder, sensitizing dye and conventional additives, which is characterized in that the photoconductive layer as a sensitizing dye is a mixture of polymethine and triarylmethane dye with a respective absorption of the dye contains between about 400 and 550 nm or 550 and 720 nm.
  • the recording material according to the invention is particularly useful when the photoconductive layer has to be further treated after decoating by decoating the non-image parts, which is necessary in the production of printing forms and printed circuits.
  • Possible sensitizing dyes to be used according to the invention from the group of the polymethine dyes with an absorption between approximately 400 and 550 nm are: astrazone yellow 3G (CI 48 055), astrazone yellow 5G (CI 48 065), basic yellow 52 115 (CI 48 060), Astrazon Yellow GRL (CI Basic Yellow 29), Astrazon Yellow 7GLL (CI Basic Yellow 21), Astra Yellow R (CI Basic Yellow 44), Astrazon Orange G (CI 48 035), Astrazon Orange R (CI 48 040) and Astrazon Orange 3R (CI Basic Orange 27 ).
  • Sensitizing dye mixtures are preferably used which contain astrazone orange R as the polymethine dye and brilliant green, crystal violet or victoria blue B as the triarylmethane dye.
  • the mixing ratio of the sensitizing dyes to one another is variable and depends, for example, on the light source present in the copier, on the absorption region of the photoconductor used and on the type of the respective sensitizer.
  • the ratio can therefore fluctuate within wide limits.
  • the spectral range of the photoconductive layer can be adapted to the lamp type used in the copying machine.
  • the conventional halogen tungsten lamps taking into account the increasing emission of these lamps in the red spectral range, it is advantageous to have a photoconductor layer which has a higher one in the short-wave spectral range or increasing sensitivity.
  • the mixing ratio of the dyes is not critical, sensitizing mixtures containing about 25 to 90 percent by weight, based on the mixture, of polymethine dye are generally preferred.
  • the proportion by weight of sensitizing dye mixture in the photoconductive layer can also be different and depends essentially on the desired or required sensitivity.
  • the amount by weight of dye mixture will generally vary between about 0.5 and about 0.001% based on the photoconductor.
  • Monomers such as polymeric aromatic and heterocyclic compounds are suitable as organic photoconductors.
  • Particularly monomers are heterocyclic compounds such as oxdiazole derivatives, which are described in German Patent 10 58 836 are used. These include, in particular, 2,5-bis (p-diethylaminophenyl) oxdiazole-1,3,4.
  • Other suitable monomeric photoconductive compounds are, for example, triphenylamine derivatives, more highly condensed aromatic compounds such as anthracene, benzo-condensed heterocycles, pyrazoline or imidazole derivatives, including triazole and oxazole derivatives as disclosed in German patents 10 60 260 and 11 20 875.
  • suitable polymers are vinylaromatic polymers such as polyvinylanthracene, polyacenaphthylene or their copolymers. Poly-N-vinylcarbazole or copolymers of N-vinylcarbazole with an N-vinylcarbazole content of at least about 40% have proven particularly useful. Also suitable are formaldehyde condensation products with various aromatics such as. B. condensates of formaldehyde and 3-bromopyrene.
  • Natural or synthetic resins are suitable as binders with regard to flexibility, film properties and adhesive strength. These include in particular polyester resins such.
  • polyester resins such as B. Mixed polyester of iso- and terephthalic acid with glycol.
  • Silicone resins such as three-dimensionally cross-linked phenylmethyl siloxanes or so-called reactive resins, as are known under the name DD lacquers, have also proven to be suitable.
  • Copolymers of styrene and maleic anhydride, but also polycarbonate resins, can also be used well.
  • the proportion by weight of binder to photoconductor in the photoconductive layer is different and will generally be greater in the presence of monomeric photoconductors, sometimes over 50%, preferably in a ratio of about 1: 1, than in the presence of polymeric photoconductors, where the binder can also be entirely absent .
  • plastic foils or plates plastic foils that have been made conductive on the surface or to prevent the penetration of solvents are used as layer support materials for the panchromatically sensitized photoconductor layers.
  • Plastic films made superficially conductive are used when an electrophotographic film material is to be produced using the panchromatically sensitized layer. If the material sensitized according to the invention is used in the field of office copying, paper is used as the carrier material.
  • metallic substrates in particular aluminum
  • the aluminum foils used are expediently roughened mechanically or electrochemically on the surface and, in special cases, anodized.
  • the electrophotographic recording material can, as conventional additives, flow control agents and plasticizers in the photoconductive layer and / or between the support and the layer ; Adhesion promoter included.
  • a panchromatic layer is first produced, as described in DE-OS 14 47 907 under Example 2.
  • 2 g of 2,5-bis (p-diethylaminophenyl) -1,3,4-oxdiazole and 2 g of a copolymer of styrene and maleic anhydride are dissolved in 40 g of methyl glycol.
  • a solution of 3 mg acridine yellow G (CI 46 025), 2 mg acridine orange (CI 46 005), 1 mg rhodamine B extra (CI 45 170) and 1 mg brilliant green (C, I, 42 040) is added to the solution in 3 ml of methanol too.
  • the total solution is applied to an aluminum foil and then the solvent is evaporated.
  • a panchromatic layer is obtained in this way. If one now determines the energy required to discharge the layer charged to -400 V in the dark to -50 V, the following values are obtained: at 487 nm 139 ⁇ J / cm 2 , at 505 nm 177 ⁇ J / cm 2 , at 532 nm 172 ⁇ J / cm 2 , at 552 nm 165 ⁇ J / cm 2 and at 650 nm 195 ⁇ J / cm 2 .
  • the comparison layer is obtained if 5 mg of astrazone orange R (CI 48 040) and 1 mg brilliant green (CI 42 040) are added to the solution of photoconductor and binder described above instead of the four dyes mentioned, a composition which corresponds to the material for curve 3 in the attached figure.
  • the 2 2 energy required to discharge the layer charged to -400 V in the dark to -50 V is 45 ⁇ J / cm 2 at 487 nm and 41 ⁇ J / cm 2 at 505 nm. at 532 nm 62 ⁇ J / cm 2 , at 552 nm 168 ⁇ J / cm 2 and at 2 650 nm 156 ⁇ J / cm 2 .
  • the solution is applied to an electrochemically roughened and anodized aluminum foil which was aftertreated in accordance with DE-OS 16 21 478 with polyvinylphosphonic acid. After the solvent has evaporated, a photoconductor layer which is sensitive in the spectral range from 400 to 700 nm is obtained, with the aid of which a printing form for offset printing is produced in the following way.
  • the layer is charged in the dark with a corona to -430 volts and exposed in a repro camera at aperture 14 for ten seconds, using 10 MH lamps of 600 W each as the light source.
  • the latent charge image is developed with a dry toner using a magnetic roller.
  • the toner image is fixed by the action of heat.
  • a panchromatic photoconductor layer for the production of a printing form for small offset printing is obtained if a solution of 5 g of 2,5-bis (p-diethylaminophenyl) -1,3,4-oxdiazole and 5 g of a copolymer of styrene and maleic anhydride are combined in one Mixture of 62 g of methylglycol, 15 g of butyl acetate (85%) and 13 g of butanone, 250 mg of astra yellow (CI Basic Yellow 44) and 50 mg of victoria pure blue (CI 42 595) are added, and this solution onto a mechanically roughened 100 ⁇ thick aluminum foil so that after evaporation of the solvent an approximately 5 micron thick layer is formed.
  • the layer is charged to -400 V in the dark and exposed in a repro camera for 20 seconds at aperture 11, 8 light bulbs of 500 watts each being used as the light source.
  • the latent charge image formed is developed with a liquid developer as described in British Patent No. 1,465,926.
  • 1.5 g of a high vacuum bitumen with a softening point of 130-140 ° is dispersed in a solution of 6.5 g of a pentaerythritol resin ester in 1000 ml of an isoparaffin with a boiling range between 185 and 210 °.
  • the photoconductor layer is removed at the non-image areas, using a solution whose preparation is described in Example 1.
  • a printing plate for small offset printing with a print run stability of 60,000 to 80,000 copies is obtained.
  • panchromatically sensitive layer for an electrophotographic film material 21 g of polyvinyl carbazole are dissolved in a mixture of 15 g of toluene, 75 g of tetrahydrofuran and 75 g of dimethylformamide. 21 mg of crystal violet (C.I. 42 555) and 7 mg of astrazon orange R (C.I. 48 040) are added to the solution and applied to a polyester film made superficially conductive by vaporization with indium tin oxide. After the solvents have evaporated, a panchromatic film material is obtained which can be used as an electrophotographic duplicating film.
  • crystal violet C.I. 42 555
  • astrazon orange R C.I. 48 040
  • the film is charged in the dark to a surface potential of -400 V and exposed in contact under a film negative, the exposure time for a 100 watt lamp at a distance of 65 cm being 10 seconds.
  • the charge image is developed with a commercially available developer, the developer particles of which are negatively charged. The result is a high-contrast film positive with good resolution.

Landscapes

  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Photoreceptors In Electrophotography (AREA)
EP79101123A 1978-04-21 1979-04-12 Matériau pour enregistrement électrophotographique Expired EP0004944B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19782817428 DE2817428A1 (de) 1978-04-21 1978-04-21 Material fuer elektrophotographische reproduktion
DE2817428 1978-04-21

Publications (3)

Publication Number Publication Date
EP0004944A2 true EP0004944A2 (fr) 1979-10-31
EP0004944A3 EP0004944A3 (en) 1979-11-14
EP0004944B1 EP0004944B1 (fr) 1983-02-09

Family

ID=6037636

Family Applications (1)

Application Number Title Priority Date Filing Date
EP79101123A Expired EP0004944B1 (fr) 1978-04-21 1979-04-12 Matériau pour enregistrement électrophotographique

Country Status (8)

Country Link
US (1) US4252880A (fr)
EP (1) EP0004944B1 (fr)
JP (1) JPS54145538A (fr)
AT (1) AT392852B (fr)
BR (1) BR7902457A (fr)
CA (1) CA1123254A (fr)
DE (2) DE2817428A1 (fr)
ZA (1) ZA791899B (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0194624A2 (fr) * 1985-03-14 1986-09-17 Hoechst Aktiengesellschaft Matériau d'enregistrement électrophotographique

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2949826A1 (de) * 1979-12-12 1981-06-19 Hoechst Ag, 6230 Frankfurt Material fuer elektrophotographische reproduktion
JPS57147656A (en) * 1981-03-09 1982-09-11 Fuji Photo Film Co Ltd Electrophotographic sensitive printing plate material
DE3210576A1 (de) * 1982-03-23 1983-10-06 Hoechst Ag Elektrophotographisches aufzeichnungsmaterial
JPS60118847A (ja) * 1983-11-30 1985-06-26 Dainippon Printing Co Ltd 画像形成材料及び画像形成方法
DE3560654D1 (en) * 1984-02-18 1987-10-22 Basf Ag Photosensitive recording material
DE3506436A1 (de) * 1985-02-23 1986-08-28 Hoechst Ag, 6230 Frankfurt Neue sulfonhaltige styrolderivate, verfahren zu deren herstellung und deren verwendung
DE3513747A1 (de) * 1985-04-17 1986-10-23 Hoechst Ag, 6230 Frankfurt Elektrophotographisches aufzeichnungsmaterial
DE3541534A1 (de) * 1985-11-25 1987-05-27 Hoechst Ag Positiv arbeitendes strahlungsempfindliches gemisch
JPH02216160A (ja) * 1989-02-17 1990-08-29 Iwatsu Electric Co Ltd 電子写真感光体
DE3938708A1 (de) * 1989-11-17 1991-05-23 Berolina Schriftbild Verfahren zur behandlung eines fotoleiters
KR20080110928A (ko) * 2001-03-10 2008-12-19 메르크 파텐트 게엠베하 유기 반도체 용액 및 분산액

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1125235A (fr) * 1954-06-02 1956-10-26 Rca Corp Procédé pour étendre la sensibilité spectrale de matières photoconductrices
FR1375297A (fr) * 1962-09-21 1964-10-16 Kalle Ag Couches sensibles pour électrophotographie et leur procédé de préparation
US3238149A (en) * 1961-07-10 1966-03-01 Method for improxvlnxg the the photocondug thqe response of dye sensitized zinc ox de
FR1488489A (fr) * 1965-07-26 1967-07-13 Ibm Procédé de reproduction électro-photographique
CH450170A (de) * 1964-01-11 1968-01-15 Kalle Ag Elektrophotographisches Mehrfarbendruckverfahren
DE1928703A1 (de) * 1968-06-06 1969-12-11 Agfa Gevaert Ag Photokonduktive Aufnahmematerialien
DE2526720A1 (de) * 1975-06-14 1976-12-16 Hoechst Ag Material fuer elektrophotographische reproduktion

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NL288684A (fr) * 1962-02-17
JPS492638B1 (fr) * 1970-11-17 1974-01-22
US4025340A (en) * 1971-11-10 1977-05-24 Fuji Photo Film Co., Ltd. Process for toning electrophotographic photosensitive material

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1125235A (fr) * 1954-06-02 1956-10-26 Rca Corp Procédé pour étendre la sensibilité spectrale de matières photoconductrices
US3238149A (en) * 1961-07-10 1966-03-01 Method for improxvlnxg the the photocondug thqe response of dye sensitized zinc ox de
FR1375297A (fr) * 1962-09-21 1964-10-16 Kalle Ag Couches sensibles pour électrophotographie et leur procédé de préparation
CH450170A (de) * 1964-01-11 1968-01-15 Kalle Ag Elektrophotographisches Mehrfarbendruckverfahren
FR1488489A (fr) * 1965-07-26 1967-07-13 Ibm Procédé de reproduction électro-photographique
DE1928703A1 (de) * 1968-06-06 1969-12-11 Agfa Gevaert Ag Photokonduktive Aufnahmematerialien
DE2526720A1 (de) * 1975-06-14 1976-12-16 Hoechst Ag Material fuer elektrophotographische reproduktion

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
RESEARCH DISCLOSURES - PRODUCT LICENSING INDEX, No. 99, Juli 1972, abstract 9913 HAMPSHIRE (UK) "Supersensitization of spectrally sensitized p-type photoconductive systems", Seiten 54-55 *
RESEARCH DISCLOSURES - PRODUCT LICENSING INDEX, Nr. 99, Juli 1972 Abstract 9912 Hampshire (UK) "Supersensitization of spectrally sensitized organic photoconductive formulations", Seiten 39-40. *
RESEARCH DISCLOSURES - PRODUCT LICENSING INDEX, Nr. 99, Juli 1972, Abstract 9913 Hampshire (UK) "Supersensitization of spectrally sensitized p-type photoconductive systems", Seiten 54-55. *

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0194624A2 (fr) * 1985-03-14 1986-09-17 Hoechst Aktiengesellschaft Matériau d'enregistrement électrophotographique
EP0194624A3 (en) * 1985-03-14 1988-08-03 Hoechst Aktiengesellschaft Electrophotographic recording material

Also Published As

Publication number Publication date
AT392852B (de) 1991-06-25
EP0004944B1 (fr) 1983-02-09
EP0004944A3 (en) 1979-11-14
ZA791899B (en) 1980-04-30
ATA296779A (de) 1990-11-15
JPS54145538A (en) 1979-11-13
CA1123254A (fr) 1982-05-11
DE2817428A1 (de) 1979-10-31
BR7902457A (pt) 1979-10-30
US4252880A (en) 1981-02-24
JPS6251462B2 (fr) 1987-10-30
DE2964691D1 (en) 1983-03-17

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