EP0004944B1 - Material für elektrophotographische Reproduktion - Google Patents

Material für elektrophotographische Reproduktion Download PDF

Info

Publication number
EP0004944B1
EP0004944B1 EP79101123A EP79101123A EP0004944B1 EP 0004944 B1 EP0004944 B1 EP 0004944B1 EP 79101123 A EP79101123 A EP 79101123A EP 79101123 A EP79101123 A EP 79101123A EP 0004944 B1 EP0004944 B1 EP 0004944B1
Authority
EP
European Patent Office
Prior art keywords
yellow
astrazon
orange
dye
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.)
Expired
Application number
EP79101123A
Other languages
German (de)
English (en)
French (fr)
Other versions
EP0004944A2 (de
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
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
Family has litigation
First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=6037636&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=EP0004944(B1) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Application filed by Hoechst AG filed Critical Hoechst AG
Publication of EP0004944A2 publication Critical patent/EP0004944A2/de
Publication of EP0004944A3 publication Critical patent/EP0004944A3/xx
Application granted granted Critical
Publication of EP0004944B1 publication Critical patent/EP0004944B1/de
Expired legal-status Critical Current

Links

Images

Classifications

    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G5/00—Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
    • G03G5/02—Charge-receiving layers
    • G03G5/04—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
    • G03G5/09—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 composed of an electrically conductive layer support which is particularly suitable for the production of printing forms or printed circuits and a panchromatically sensitized photoconductive layer composed of organic photoconductor, binder, sensitizing dye from a mixture of water-soluble polymethine and triaryl methane dye and customary additives, which characterized in that the photoconductive layer as polymethine dye astrazone orange R (CI 48 040), astrazone orange G (CI 48 035), astrazone yellow 3G (CI 48055), astrazone yellow 5G (CI 48065), basic yellow 52115 (CI 48 060), astrazone yellow GRL (CI Basic Yellow 29), Astrazongelb 7GLL (CI Basic Yellow 21), Astragelb R (CI Basic Yellow 44) or Astrazonorange 3R (CI Basic Orange 27) and as triarylmethane dye malachite green (CI 42 000), brilliant green (CI 42 040) , Acid violet 6BN (CI 42 552), crystal violet (C.
  • the photoconductive layer
  • 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.
  • the amount of dyes to be used also decreases depending on the type of photoconductor used. Since the sensitizer dyes are generally salts whose addition to the photoconductor layer causes a certain dark conductivity, the use of a smaller amount very often brings about improved electrophotographic properties of the layer. Panchromatic sensitization in itself has advantages in that the light provided by the light sources used in reproduction technology is better utilized. In practice, this means shorter exposure times and thus time and energy savings. It is also possible, because of the improved properties, to reduce the proportion of photoconductor in the photoconductive layer.
  • the recording material in the photoconductive layer preferably contains astrazone orange R as the sensitizing dye and brilliant green or crystal violet or victoria blue B.
  • 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 by a certain mixture. When using 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 or increasing sensitivity in the short-wave spectral range.
  • 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 5 and about 0.001% based on the photoconductor.
  • Monomers such as polymeric aromatic and heterocyclic compounds are suitable as organic photoconductors.
  • Particularly heterocyclic compounds such as oxdiazole derivatives, which are mentioned in German patent 1,058,836, are used as monomers. These include, in particular, 2,5-bis (p-diethylaminaphenyl) axdiazal-1,3,4.
  • Other suitable monomeric photoconductive compounds are, for example, triphenylamine derivatives, more highly condensed aromatic compounds such as anthracene, benzo-fused heterocycles, pyrazoline or imidazole derivatives, including triazole and oxazole derivatives as disclosed in German Patents 1,060,260 and 1,120,875 .
  • 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 made superficially conductive or specially made conductive foils against the penetration of solvents are suitable 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 layer supports 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 contain leveling agents and plasticizers as conventional additives in the photoconductive layer and / or adhesion promoters between the layer support and the layer.
  • a panchromatic layer is first produced, as described in DE-OS 1 447 907 under Example 2. To do this, dissolve 2 g
  • the comparison layer is obtained if 5 mg of astrazone orange R (C. 1. 48 040) and 1 mg of 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 energy required to discharge the layer charged to -400 V in the dark to -50 V is 45 ⁇ J / cm 2 at 487 nm, 41 ⁇ J / cm 2 at 505 nm, 62 ⁇ J / cm 2 at 532 nm, and 168 at 552 nm ⁇ J / cm 2 and at 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 1621 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 resulting latent charge pattern 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 -400V 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 resulting latent charge image is developed with a liquid developer as described in British Patent No. 1465 926.
  • a liquid developer as described in British Patent No. 1465 926.
  • 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 circulation stability of 60,000 to 80,000 copies is obtained.
  • panchromatically sensitive layer for an electrophotograph
  • the film material is dissolved in 21 g of polyvinyl carbazole in a mixture of 150 g of toluene, 75 g of tetrahydrofuran and 75 g of dimethylformamide.
  • 21 mg of crystal violet (CI 42 555) and 7 mg of astrazone orange R (CI 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.
  • 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 Material für elektrophotographische Reproduktion Expired EP0004944B1 (de)

Applications Claiming Priority (2)

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

Publications (3)

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

Family

ID=6037636

Family Applications (1)

Application Number Title Priority Date Filing Date
EP79101123A Expired EP0004944B1 (de) 1978-04-21 1979-04-12 Material für elektrophotographische Reproduktion

Country Status (8)

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

Families Citing this family (12)

* 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
DE3509147A1 (de) * 1985-03-14 1986-09-18 Hoechst Ag, 6230 Frankfurt Elektrophotographisches aufzeichnungsmaterial
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
WO2002072714A1 (de) * 2001-03-10 2002-09-19 Covion Organic Semiconductors Gmbh Lösung und dispersionen organischer halbleiter

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE538610A (sv) * 1954-06-02
US3238149A (en) * 1961-07-10 1966-03-01 Method for improxvlnxg the the photocondug thqe response of dye sensitized zinc ox de
NL137097C (sv) * 1962-02-17
FR1375297A (fr) * 1962-09-21 1964-10-16 Kalle Ag Couches sensibles pour électrophotographie et leur procédé de préparation
DE1447907A1 (de) * 1964-01-11 1968-12-05 Kalle Ag Elektrophotographischer Mehrfarbendruck
US3512966A (en) * 1965-07-26 1970-05-19 Ibm Process of electrophotographic recording employing persistent organic photoconductive compositions
JPS492638B1 (sv) * 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
AU507694B2 (en) * 1975-06-14 1980-02-21 Hoechst Aktiengesellschaft Electrophotographic reproduction

Non-Patent Citations (1)

* 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 *

Also Published As

Publication number Publication date
BR7902457A (pt) 1979-10-30
JPS54145538A (en) 1979-11-13
JPS6251462B2 (sv) 1987-10-30
ZA791899B (en) 1980-04-30
AT392852B (de) 1991-06-25
US4252880A (en) 1981-02-24
EP0004944A2 (de) 1979-10-31
DE2964691D1 (en) 1983-03-17
EP0004944A3 (en) 1979-11-14
CA1123254A (en) 1982-05-11
DE2817428A1 (de) 1979-10-31
ATA296779A (de) 1990-11-15

Similar Documents

Publication Publication Date Title
DE2941509C2 (de) Elektrophotographisches Aufzeichnungsmaterial
DE2954414C2 (sv)
DE3347905C2 (sv)
EP0004944B1 (de) Material für elektrophotographische Reproduktion
EP0001599A1 (de) Elektrophotographisches Aufzeichnungsmaterial und dessen Verwendung in einem Kopierverfahren
DE1058836B (de) Material fuer elektrophotographische Reproduktion
DE1622364B2 (de) Elektrophotographisches aufzeichnungsmaterial
DE2009346A1 (de) Elektrophotographisches Aufzeichnungsmaterial
DE1522644B2 (de) Verwendung persistenter organischer photoleiter in einem elektrophotographischen aufzeichnungsverfahren
DE2160812C2 (de) Elektrophotographisches Aufzeichnungsmaterial
EP0201725B1 (de) Elektrophotographisches Aufzeichnungsmaterial
EP0093329B1 (de) Elektrographische Aufzeichnungsmaterialien mit speziellen Ladungsträger transportierenden Verbindungen
EP0131215B1 (de) Elektrophotographische Aufzeichnungsmaterialien mit verbesserter Photoempfindlichkeit
DE1943386B2 (de) Elektrophotographisches aufzeichnungsmaterial
EP0093330A1 (de) Elektrographische Aufzeichnungsmaterialien mit speziellen Ladungsträger transportierenden Verbindungen
DE1921246B2 (de) Elektrophotographisches aufzeichnungsmaterial
EP0152047B1 (de) Elektrophotographisches Aufzeichnungsmaterial
DE1797137A1 (de) Elektrophotographisches Aufzeichnungsmaterial
EP0194624B1 (de) Elektrophotographisches Aufzeichnungsmaterial
DE2016395B2 (de) Elektrophotographisches Aufzeichnungsmaterial
DE2059540B2 (de) Elektrophotographisches Aufzeichnungsmaterial mit einer photoleitfänigen Schicht
DE2726116A1 (de) Material zur herstellung von druckformen
DE2126660A1 (de) Elektrophotographisches Aufzeichnungsmaterial
DE1959181C3 (de) Elektrophotographisches Aufzeichnungsmaterial
DE3148760C2 (de) Elektrophotographisches Aufzeichnungsmaterial

Legal Events

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

Free format text: ORIGINAL CODE: 0009012

PUAL Search report despatched

Free format text: ORIGINAL CODE: 0009013

AK Designated contracting states

Designated state(s): BE CH DE FR GB IT NL SE

AK Designated contracting states

Designated state(s): BE CH DE FR GB IT NL SE

17P Request for examination filed
ITF It: translation for a ep patent filed
GRAA (expected) grant

Free format text: ORIGINAL CODE: 0009210

AK Designated contracting states

Designated state(s): BE CH DE FR GB IT NL SE

REF Corresponds to:

Ref document number: 2964691

Country of ref document: DE

Date of ref document: 19830317

ET Fr: translation filed
PLBI Opposition filed

Free format text: ORIGINAL CODE: 0009260

26 Opposition filed

Opponent name: BASF AKTIENGESELLSCHAFT

Effective date: 19831105

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

Ref country code: SE

Payment date: 19840331

Year of fee payment: 6

PLBN Opposition rejected

Free format text: ORIGINAL CODE: 0009273

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

Free format text: STATUS: OPPOSITION REJECTED

27O Opposition rejected

Effective date: 19850920

NLR2 Nl: decision of opposition
PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: SE

Effective date: 19860413

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

Ref country code: BE

Payment date: 19890413

Year of fee payment: 11

ITTA It: last paid annual fee
PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: CH

Payment date: 19890626

Year of fee payment: 11

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

Ref country code: CH

Effective date: 19900430

Ref country code: BE

Effective date: 19900430

BERE Be: lapsed

Owner name: HOECHST A.G.

Effective date: 19900430

REG Reference to a national code

Ref country code: CH

Ref legal event code: PL

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

Ref country code: FR

Payment date: 19920306

Year of fee payment: 14

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

Ref country code: NL

Payment date: 19920430

Year of fee payment: 14

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

Ref country code: GB

Payment date: 19930319

Year of fee payment: 15

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

Ref country code: NL

Effective date: 19931101

NLV4 Nl: lapsed or anulled due to non-payment of the annual fee
PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: FR

Effective date: 19931229

REG Reference to a national code

Ref country code: FR

Ref legal event code: ST

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

Ref country code: GB

Effective date: 19940412

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

Ref country code: DE

Payment date: 19940616

Year of fee payment: 16

GBPC Gb: european patent ceased through non-payment of renewal fee

Effective date: 19940412

EUG Se: european patent has lapsed

Ref document number: 79101123.2

Effective date: 19870224

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

Ref country code: DE

Effective date: 19960201