EP0201725B1 - Matériel d'enregistrement pour l'électrophotographie - Google Patents

Matériel d'enregistrement pour l'électrophotographie Download PDF

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Publication number
EP0201725B1
EP0201725B1 EP86104860A EP86104860A EP0201725B1 EP 0201725 B1 EP0201725 B1 EP 0201725B1 EP 86104860 A EP86104860 A EP 86104860A EP 86104860 A EP86104860 A EP 86104860A EP 0201725 B1 EP0201725 B1 EP 0201725B1
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EP
European Patent Office
Prior art keywords
recording material
photoconductive layer
photoconductor
layer contains
sensitizing dye
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 - Lifetime
Application number
EP86104860A
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German (de)
English (en)
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EP0201725A3 (en
EP0201725A2 (fr
Inventor
Werner Dr. Dipl.-Chem. Franke
Richard Brahm
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Hoechst AG
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Hoechst AG
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Publication date
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Publication of EP0201725A3 publication Critical patent/EP0201725A3/de
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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
    • G03G5/06—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being organic
    • G03G5/0664—Dyes
    • G03G5/0666—Dyes containing a methine or polymethine group
    • G03G5/0668—Dyes containing a methine or polymethine group containing only one methine or polymethine group
    • G03G5/067—Dyes containing a methine or polymethine group containing only one methine or polymethine group containing hetero rings

Definitions

  • the present invention relates to an electrophotographic recording material consisting of an electrically conductive support and at least one photoconductive layer containing organic photoconductor, sensitizing dye, binder and conventional additives.
  • photoconductors for electrophotographic reproduction which are sensitive to radiation down to the short-wave visible part of the spectrum and whose radiation sensitivity in the visible part of the spectrum can be expanded by adding one or more sensitizing dyes which transmit longer-wave energy to transmit the energy Are capable of light on the photoconductor.
  • sensitizing dyes which transmit longer-wave energy to transmit the energy Are capable of light on the photoconductor. This includes dyes from a wide variety of compound classes.
  • panchromatic sensitizations have advantages in that the light sources used in reproduction technology with a high proportion of red are better used. In practice, this means shorter exposure times and thus time and energy savings. One can, also because of the improved Sensitivities, reduce the proportion of photoconductor in the photoconductive layer.
  • the disadvantage of such a continuous sensitization is that the material cannot be processed under physiologically favorable, bright darkroom light.
  • the present invention was based on the object of electrophotographic recording material with organic photoconductor into the near infrared using a sensitizer whose sensitization maximum is longer than about 620 nm, especially for light sources which emit in the near infrared or / and in the border region of the visible region to infrared. sensitize in such a way that it is also possible to process the recording material in bright darkroom light, for example yellow or green light, without damage.
  • n 2 or 3
  • X ⁇ mean a monovalent anion.
  • chloride, bromide or iodide are suitable as anions.
  • the photoconductive layer preferably contains a cyanine dye with a sensitization maximum between 650 and 840 nm. These include in particular the penta- and the heptamethine cyanine.
  • the curve shows corresponding sensitization spectrograms, which are obtained by exposure to a high-pressure xenon lamp through an interference filter with a linear stepless gray wedge.
  • FIGS. 2 and 3 show that the sensitization of the dyes is also significantly longer-wavelength than their absorption in ethanol.
  • the sensitization according to the invention it is possible to provide a recording material which is dark chamber-safe for green and / or yellow light and which has a sensitization with a maximum in the range between 650 and 840 nm and, because of its sensitization reaching into the infrared, good utilization of the Allows light emission from light sources that emit mainly or selectively in the near infrared or into the near infrared, such as III / V LED diodes, lasers or incandescent lamps.
  • the residual color of the photoconductive layer is also significantly less than when using appropriate triphenylmethane dyes.
  • the sensitizing dyes according to the invention are prepared by the procedures customary in the chemistry of the sensitizing dyes for silver halide emulsions and known to the person skilled in the art (A. Claisen, B. 36, 3667 (1903) or GB-PS 354.826).
  • the concentration of the sensitizing dye according to the invention depends on the photoconductor used in the individual case, the desired effect and also on the sensitizing dyes used themselves. Usually from about 0.05 to about 3 percent by weight, based on the weight of the photoconductor, is added.
  • the photoconductive layer with charge-generating compound and charge-transporting compound can be in either a single or a double layer arrangement.
  • the single-layer arrangement is preferred.
  • Oxazole derivatives such as 2-vinyl-4- (2'-chlorophenyl) -5- (4'-diethylaminophenyl) oxazole, described in DE-PS 10 60 260 (corresponding to US Pat. No. 3,112,197) or 11 20 875 (corresponding to US Pat. No. 3,257,203), or 2-phenyl-4- (2'-chlorophenyl) -5- (4'-diethylaminophenyl) oxazole or also oxdiazole derivatives, such as 2,5-bis (4'-diethylaminophenyl ) -1,3,4-oxdiazole, described in DE-PS 10 58 836 (corresponding to US-PS 3,189,447) used. Hydrazone or pyrazoline derivatives can also be used, such as p-methoxy-benzaldehyde diphenyl hydrazone or 3-methoxyphenyl-1,5-diphenyl-pyrazoline.
  • polyester resins such as mixed polyesters of iso- and terephthalic acid with glycol, or silicone resins, such as three-dimensionally cross-linked phenylmethylsiloxanes, or so-called reaction resins, as are known under the name DD lacquers, are suitable.
  • Polycarbonate resins can also be used well.
  • Recording materials for the production of printing forms are particularly suitable for binders which are soluble in aqueous or alcoholic solvent systems, if appropriate with the addition of acid or alkali.
  • Alkali-soluble binders are preferably used.
  • Suitable binders are then high-molecular substances which carry alkali-solubilizing groups, such as acid anhydride, carboxyl, phenol, sulfonic acid, sulfonamide or sulfonimide groups.
  • Copolymers with anhydride groups can be used with particularly good success, since the lack of free acid groups means that the dark conductivity of the photoconductive layer is low despite good alkali solubility.
  • the preferred alkali-soluble binders include styrene / maleic anhydride copolymers, acrylic or methacrylic acid-containing copolymers, such as hexyl methacrylate / methacrylic acid / styrene copolymer, or phenolic resin alone or in a mixture.
  • the supports of the recording material can be flat or cylindrical and, in a known manner, consist of a metal plate, a metal foil, of metallized papers or of papers or foils which are coated with an electrically conductive plastic or other conductive inorganic or organic substances.
  • the layer support is preferably formed from a metal base or a metallized film.
  • toner images can be produced on the recording material according to the invention, but it is also possible to transfer either the charge image produced or the toner image to an image-receiving material.
  • the electrophotographic recording material can contain leveling agents and plasticizers and / or adhesion promoters as conventional additives in the photoconductive layer and / or between the support and photoconductive layer.
  • a printing plate for offset printing was produced from this recording material in the following manner.
  • the photoconductive layer was charged to -430 V in the dark using a corona.
  • the exposure was carried out with a repro camera at aperture 14 for ten seconds, using 10 MH lamps of 600 W power each as the light source.
  • the resulting latent charge image was developed with a commercially available dry toner using a magnetic roller and the toner image was fixed by heat.
  • the layer was charged to about -450 V with a corona and exposed in a repro camera with 8 autophot lamps of 500 watts each for 250 seconds.
  • the assembly of a printed circuit on a signature with red markings and orientation lines served as a template. The markings on the copied film were not reproduced due to the light sensitivity of the photoconductor layer in this spectral range.
  • 7.5 g of a copolymer of styrene and maleic anhydride were added to a solution of 75 mg of the sensitizing dye of the formula 1 in 90 g of a solvent mixture consisting of 140 g of tetrahydrofuran, 40 g of butyl acetate and 90 g of methyl glycol (SCRIPSET R 540, Monsanto, USA) slowly added with stirring at room temperature, stirred for 15 minutes. Then 15 g of the photoconductor 2,5-bis- (4'-diethylaminophenyl) -1,3,4-oxdiazole were added.
  • the coating solution was then spun onto a surface-brushed aluminum support to a dry layer weight of about 5 g / m 2 and further processed in the usual manner as described in Example 1.
  • the material could be processed in green darkroom light.
  • the solutions were poured onto brushed aluminum sheets, so that after drying layers of a thickness of approx. 6 g / m2.
  • the photoconductor layers in the dark were negatively charged under a corona and exposed through a spectral filter.

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  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Photoreceptors In Electrophotography (AREA)

Claims (14)

  1. Matériel d'enregistrement électrophotographique, comprenant un support de couche conducteur de l'électricité et au moins une couche photoconductrice comportant un photoconducteur organique, un colorant de sensibilisation, un liant et des additifs courants, caractérisé en ce que la couche photoconductrice renferme, comme colorant de sensibilisation, au moins un composé de formule générale
    Figure imgb0005
     dans laquelle n = 2 ou 3 et X⁻ représente un anion monovalent.
  2. Matériel d'enregistrement selon la revendication 1, caractérisé en ce que la couche photoconductrice renferme un colorant cyanine présentant un maximum de sensibilisation entre 650 et 840 nm.
  3. Matériel d'enregistrement selon la revendication 1 ou 2, caractérisé en ce que la couche photoconductrice renferme, comme colorant de sensibilisation, de la pentaméthinecyanine.
  4. Matériel d'enregistrement selon la revendication 1 ou 2, caractérise en ce que la couche photoconductrice renferme, comme colorant de sensibilisation, de l'heptaméthinecyanine.
  5. Matériel d'enregistrement selon la revendication 1, caractérisé en ce que la couche photoconductrice renferme un mélange de colorants de sensibilisation ayant la formule générale de la revendication 1.
  6. Matériel d'enregistrement selon l'une des revendications 1 à 5, caractérisé en ce que le photoconducteur organique est choisi dans le groupe formé par les dérivés de l'oxazole, de l'oxadiazole, de l'hydrazone ou de la pyrazoline,
  7. Matériel d'enregistrement selon la revendication 6, caractérisé en ce que le photoconducteur est le 2,5-bis-(4'-diéthylaminophényl)-1,3,4-oxadiazole.
  8. Matériel d'enregistrement selon la revendication 6, caractérisé en ce que le photoconducteur est le 2-vinyl-4-(2'-chlorophényl)-5-(4'-diéthylaminophényl)- oxazole.
  9. Matériel d'enregistrement selon la revendication 6, caractérisé en ce que le photoconducteur est le 2-phényl-4-(2'-chlorophényl)-5-(4'-diéthylaminophényl)-oxazole.
  10. Matériel d'enregistrement selon la revendication 6, caractérisé en ce que le photoconducteur est la 3-méthoxyphényl-1,5-diphénylpyrazoline.
  11. Matériel d'enregistrement selon la revendication 6, caractérisé en ce que le photoconducteur est la diphénylhydrazone de p-méthoxybenzaldéhyde.
  12. Matériel d'enregistrement selon la revendication 1, pour la fabrication de plaques d'impression comportant une base métallique ou un film métallisé comme support de couche.
  13. Matériel d'enregistrement selon l'une des revendications 1 à 12, caractérisé en ce que la couche photoconductrice renferme un liant soluble dans une base alcaline.
  14. Matériel d'enregistrement selon la revendication 13, caractérisé en ce que la couche photoconductrice renferme, comme liant soluble dans une base alcaline, un copolymère styrène-anhydride d'acide maléique, un copolymère renfermant de l'acide acrylique ou méthacrylique, ou une résine phénolique seule ou en mélange.
EP86104860A 1985-04-17 1986-04-09 Matériel d'enregistrement pour l'électrophotographie Expired - Lifetime EP0201725B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19853513747 DE3513747A1 (de) 1985-04-17 1985-04-17 Elektrophotographisches aufzeichnungsmaterial
DE3513747 1985-04-17

Publications (3)

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EP0201725A2 EP0201725A2 (fr) 1986-11-20
EP0201725A3 EP0201725A3 (en) 1988-08-03
EP0201725B1 true EP0201725B1 (fr) 1992-03-18

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EP86104860A Expired - Lifetime EP0201725B1 (fr) 1985-04-17 1986-04-09 Matériel d'enregistrement pour l'électrophotographie

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US (1) US4681827A (fr)
EP (1) EP0201725B1 (fr)
JP (1) JPS61241764A (fr)
DE (2) DE3513747A1 (fr)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0823707B2 (ja) * 1987-04-22 1996-03-06 富士写真フイルム株式会社 スキヤンニング露光工程を含む画像形成方法
GB8712151D0 (en) * 1987-05-22 1987-06-24 Minnesota Mining & Mfg Dyes
JP2589376B2 (ja) * 1989-06-13 1997-03-12 三田工業株式会社 感光性トナー
WO1992011581A1 (fr) * 1990-12-21 1992-07-09 Eastman Kodak Company Imagerie photo-electrographique au moyen de colorants de sensibilisation a l'infrarouge proche
US5256510A (en) * 1990-12-21 1993-10-26 Eastman Kodak Company Photoelectrographic imaging with near-infrared sensitizing dyes
US5288582A (en) * 1991-07-29 1994-02-22 Eastman Kodak Company Photoelectrographic method for printing
US5240800A (en) * 1991-07-29 1993-08-31 Eastman Kodak Company Near-infrared radiation sensitive photoelectrographic master and imaging method
JPH0566597A (ja) * 1991-09-09 1993-03-19 Oji Paper Co Ltd レーザー光用電子写真平版印刷版材料
US5403686A (en) * 1993-09-27 1995-04-04 Eastman Kodak Company Electrophotographic element and imaging method exhibiting reduced incidence of laser interference patterns

Family Cites Families (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB354826A (en) * 1930-05-15 1931-08-17 Frances Mary Hamer Improvements in or relating to the manufacture of dyes
NL99369C (fr) * 1956-06-04
LU35237A1 (fr) * 1956-06-27
NL242505A (fr) * 1958-08-20
DE1447907A1 (de) * 1964-01-11 1968-12-05 Kalle Ag Elektrophotographischer Mehrfarbendruck
ZA6807938B (fr) * 1967-12-04
GB1282423A (en) * 1968-12-16 1972-07-19 Agfa Gevaert Spectral sensitization of photoconductive compositions
DE2214055A1 (de) * 1972-03-23 1973-09-27 Agfa Gevaert Ag Sensibilisierte elektrophotographische schichten
US4066453A (en) * 1973-05-02 1978-01-03 Hoechst Aktiengesellschaft Process for the preparation of printing forms
DE2353639C2 (de) * 1973-10-26 1983-08-04 Hoechst Ag, 6230 Frankfurt Elektrophotographisches Aufzeichnungsmaterial
AU507694B2 (en) * 1975-06-14 1980-02-21 Hoechst Aktiengesellschaft Electrophotographic reproduction
JPS54121741A (en) * 1978-03-14 1979-09-21 Fuji Xerox Co Ltd Photosensitive material for electrophotography
DE2817428A1 (de) * 1978-04-21 1979-10-31 Hoechst Ag Material fuer elektrophotographische reproduktion
US4418135A (en) * 1982-09-22 1983-11-29 Allied Corporation Thermally-stable, infrared-sensitive zinc oxide electrophotographic compositions element and process
ZA839316B (en) * 1982-12-16 1984-08-29 Vickers Plc Photoconductive compositions
JPS59216146A (ja) * 1983-05-24 1984-12-06 Sony Corp 電子写真用感光材料

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Publication number Publication date
JPS61241764A (ja) 1986-10-28
DE3513747A1 (de) 1986-10-23
DE3684357D1 (de) 1992-04-23
US4681827A (en) 1987-07-21
EP0201725A3 (en) 1988-08-03
EP0201725A2 (fr) 1986-11-20

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