EP0161648A1 - Matériau d'enregistrement électrophotographique - Google Patents

Matériau d'enregistrement électrophotographique Download PDF

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Publication number
EP0161648A1
EP0161648A1 EP85105785A EP85105785A EP0161648A1 EP 0161648 A1 EP0161648 A1 EP 0161648A1 EP 85105785 A EP85105785 A EP 85105785A EP 85105785 A EP85105785 A EP 85105785A EP 0161648 A1 EP0161648 A1 EP 0161648A1
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EP
European Patent Office
Prior art keywords
layer
recording material
organic
material according
weight
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
EP85105785A
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German (de)
English (en)
Other versions
EP0161648B2 (fr
EP0161648B1 (fr
Inventor
Jürgen Dr. Dipl.-Chem. Lingnau
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Hoechst AG
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Hoechst AG
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Application filed by Hoechst AG filed Critical Hoechst AG
Priority to AT85105785T priority Critical patent/ATE29603T1/de
Publication of EP0161648A1 publication Critical patent/EP0161648A1/fr
Application granted granted Critical
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Publication of EP0161648B2 publication Critical patent/EP0161648B2/fr
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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
    • G03G5/06—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being organic
    • G03G5/0601—Acyclic or carbocyclic compounds
    • G03G5/0609—Acyclic or carbocyclic compounds containing oxygen
    • 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
    • G03G5/06—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being organic
    • G03G5/0622—Heterocyclic compounds
    • G03G5/0644—Heterocyclic compounds containing two or more hetero rings
    • G03G5/0646—Heterocyclic compounds containing two or more hetero rings in the same ring system
    • G03G5/0657—Heterocyclic compounds containing two or more hetero rings in the same ring system containing seven relevant rings

Definitions

  • the invention relates to an electrophotographic recording material consisting of an electrically conductive support, optionally an insulating barrier layer and a photoconductive layer.
  • the recording material is suitable for repeated or single use in copiers, as a printing form or as a printed circuit.
  • Color pigments which generate charge carriers include perinones (DE-OS 22 39 923, corresponding to GB-PS 1.416.603, DE-OS 21 08 958, corresponding to US Pat. No. 3,879,200), perylenetetracarboxylic acid diimides (DE-OS 22 37 539, corresponding to US Pat. PS 3,871,882, DE-OS 21 08 992, corresponding to US-PS 3,904,407) and condensed quinones (DE-OS 22 37 678, corresponding to US-PS 4,315,981, DE-OS 21 08 935, corresponding to US-PS 3,877,935) are used.
  • the systems described ge together is a double-layer structure with a lower layer, which generates charge carriers and has a low layer thickness with a high concentration of color pigment, and a relatively thick charge transport layer made of inert binder and organic p-conducting photoconductor.
  • layer arrangements are specified in which the sensitizing color pigment and the p-type photoconductor are applied together in one layer on the electrically conductive layer support.
  • the concentration of the color pigment is only 0.1 to 5 percent by volume of the photoactive layer.
  • organic p-conducting photoconductor - aromatic or heterocyclic compounds - must be present in the layer in a concentration of at least 25 percent by volume in order to achieve sensibilities which can be used in practice.
  • Electronically inert polymers such as polystyrene, polyacrylate, cellulose nitrate, polyvinyl acetate, chlorinated rubber and many others are described as binders
  • Electrophotographic layers consist of a photoconductive pigment and an electronically inert binder.
  • Zinc oxide for example in US Pat. No. 3,121,006, cadmium sulfide, for example in US Pat. No. 3,238,150, and a number of other inorganic compounds are described as photoconductive pigments.
  • the charge transport in these layers is due to a high concentration of the photoconductor capable pigments. With such a layer structure, a pigment concentration of over 50 percent by volume is required in order to enable particle contact of the photoconductive particles.
  • DE-OS 32 27 475 corresponding to US Pat. No.
  • part of the inorganic pigment can also be replaced by organic, photoconductive pigments, the pigments such as CI Pigment Red 168 and CI Pigment Orange 43 having proven themselves equally well, the derivatives of Represent naphthalene tetracarboxylic acid diimides.
  • the total amount of photoconductor in the layer required for practical use is between 20 and 80 percent by weight.
  • monolayers for positive charging can also be produced from Cu phthalocyanine in e-form (JP-AS 50/38543).
  • the resulting ⁇ complex shows good sensitivity with poly-N-vinylcarbazole as a binder / p-type photoconductor (50:50).
  • photoconductors with a double layer arrangement are used.
  • this arrangement has the disadvantage that it is produced in two coating application steps, which is more complex than the production of a monolayer material. It is also disadvantageous in the case of double-layer arrangements that they have an unfavorable residual charge behavior.
  • monolayers based on zinc oxide can be used for cyclic image reproduction, which have low residual charge potentials. Due to the large proportion of zinc oxide, however, layers of this type show a relatively low mechanical stability and a relatively poor charge acceptance.
  • Double-layer photoconductors with a roughly equal pre-coat of pigment and binder and top coat of p-conductive photoconductor and binder according to German patent application, file number P 33 29 442.9, can be used for the electrophotographic production of offset printing plates, but are significantly less sensitive than the first and from Manufacturing costs also unfavorable.
  • Monolayer photoconductors with dissolved sensitizing dyes (DE-OS 25 26 720, corresponding to US Pat.
  • the present invention was therefore based on the object of providing an electrophotographic recording material which can be produced simply and inexpensively, has great photosensitivity and large voltage contrasts with good negative charge acceptance and leads to low residual potentials after exposure. At the same time, the mechanical properties should enable use on a flexible substrate or a lamination step.
  • Another object of the invention was to make the recording material applicable for the production of printing forms and printed circuits (printed circuit boards) by using suitable binders and low concentration of the p-type photoconductor.
  • the photoconductive layer has at least one electronic, n-conductive pigment in a concentration of between 10 and 50 percent by weight, based on the layer weight, at least one electronically contains inert carbonyl group-containing binder and organic p-type photoconductor in a concentration from zero to 20 percent by weight, based on the layer weight.
  • the recording material in the photoconductive layer contains the organic n-type pigment in a concentration between 15 and 30 percent by weight and the organic p-type photoconductor in a concentration of 2 to 8 percent by weight, based on the layer weight.
  • concentrations of 20-30 percent by weight for the organic, n-type pigment and of 2-5 percent by weight for the organic, p-type photoconductor have proven successful.
  • the organic p-type photoconductor can be present in the layer in a homogeneously distributed form, but it can also be present in a gradient distribution by diffusion into the layer or else in a step-like distribution by double-layer arrangement.
  • Pigments of the following general formulas I to IV can be used as the n-conducting pigment.
  • pigments are referred to in a number of publications as photoconductive, which means, however, that photoconductivity is regularly understood in cooperation with other photoconductors.
  • the color pigments play the role of the sensitizer, which forms charge carriers in cooperation with the p-type photoconductor.
  • pigments are used either in very thin layers that generate charge carriers or, in the case of homogeneous distribution, in a relatively low concentration. As described above, according to US Pat. No. 3,879,200 and US Pat. No. 3,904,407, good electrophotographic properties can only be achieved in these cases.
  • the utilization of the n-conductivity of pigments used according to the invention requires a minimum pigment concentration, which is to be set at about 10 percent by weight, based on the layer weight. Excessively high pigment concentrations lead to a deterioration in the charge acceptance, so that approximately 50% by weight of pigment is to be regarded as the upper limit. Pigment concentrations between 15 and 30 percent by weight have proven particularly successful. At these pigment concentrations, especially in the higher range, when the alkali-soluble binders according to the invention are used, the decoating ability of the photoconductive layer for use in electrophotographic imageable printing forms and the like also remains. Like. Guaranteed.
  • n-type pigments When using n-type pigments according to the invention, an increase in sensitivity was found if p-type photoconductors were added to the layer to a small extent.
  • Compounds which are usually used in electrophotographic layers are suitable as such. Examples are oxdiazoles, oxazoles, aromatic amines, triphenylmethanes, hydrazones, but also polymeric compounds, such as polyvinyl carbazole, as described, for example, in German patents 10 58 836, 10 60 260, 11 20 875, 11 97 325 and 10 68 115 and 11 11 935 emerge.
  • the concentration of the p-type photoconductor should not exceed 20 percent by weight, based on the layer weight. Concentrations between 2 and 8 percent by weight have proven particularly useful.
  • the p-conductivity of the photoconductor only contributes to the generation of charge carriers and to the removal of the positive charge carriers in the upper region of the photoconductive layer.
  • the addition of p-type photoconductor can therefore also be restricted to these upper zones, which has proven to be advantageous particularly in the case of thicker layers in an arrangement in the upper region.
  • a targeted addition of the p-type photoconductor into the upper zones can either be achieved by means of a double-layer structure achieve or by post-treatment of the finished layer not containing the p-type photoconductor with appropriate solutions of the photoconductor which are applied without a binder.
  • Such electronically inert binders containing carbonyl groups are used which are soluble or dispersible in aqueous alkaline solution.
  • Copolymers of methacrylic acid esters and methacrylic acid, optionally with other monomers such as acrylic acid, styrene, are preferably used for this purpose.
  • binders whose glass transition temperature is significantly lower have proven suitable for use as an electrophotographic dry resist. Only in such a case can a complete transfer of the photoconductive layer be achieved with a lamination layer. Copolymers of the monomers acrylic acid, longer-chain acrylic or methacrylic acid esters, optionally in combination with other monomers such as methacrylic acid, styrene, have proven particularly useful as binders. There are no restrictions on the glass transition temperature of the binder for use as a liquid resist.
  • the thickness of the photoconductive layer depends primarily on the intended use. In order to ensure sufficient charge acceptance, it should not be less than about 3 g / m 2 .
  • it is expediently between about 5 and 30 g / m 2 , for photoconductor tapes or drums in copiers between about 10 and 20 g / m 2 and for laminatable material between about 20 and 50 g / m 2 . A sharp increase in the residual potential with the layer weight cannot be observed.
  • the coating with the photoconductive layer is carried out in the usual way from the solution, for example by doctor or spray application.
  • the application is preferably made with a flow machine.
  • the layer is dried, for example, in drying channels.
  • the recording material according to the invention can also be produced for the application of the dry resists by applying the photoconductive layer to the electrically conductive layer support by lamination under heat and pressure from an intermediate support, for example a polyethylene terephthalate film. Because of the relatively low proportion of p-type photoconductor, the recording material according to the invention can be used in the form of a layer support and a coating solution as a liquid resist. In this case, it is up to the user to apply the coating using a wipe-on process.
  • Such a small layer thickness serves as an insulating barrier layer.
  • polymers can be used which bring about better adhesion of the photoconductive layer to the carrier material, for example UV or thermally curable systems. It can happen but also act as insulating metal oxide layers, for example aluminum oxide, which bring about hydrophilization of the carrier surface.
  • the layer thickness of the insulating barrier layer should not exceed 4 g / m 2 .
  • Metals can be used as the electrically conductive layer supports, but plastic supports metallized by vapor deposition or lamination can also be used. In addition, plastics with a conductive coating made of polymeric binders and conductive materials such as metal powders or graphite dust can be used.
  • a conductive coating made of polymeric binders and conductive materials such as metal powders or graphite dust can be used.
  • plates made of roughened and anodized aluminum are preferably used as layer supports.
  • the preferred support is copper or has a copper surface such as copper clad polyamide film.
  • the layer contains substances which are added to the coating solution as conventional additives, which may be up to 5% by weight in the photoconductive layer. They improve the surface structure and the flexibility of the layer. These can be, for example, plasticizers, such as triphenyl phosphate, or leveling agents, such as silicone oils.
  • the layer obtained after drying is dark red and matt.
  • Hostapermorange GR Pigment Orange 43, CI 71 105, Formula I
  • a solution of 10 g of polybutyl methacrylate R Plexigum P 676, Röhm GmbH
  • Example 2 The procedure was as in Example 2, with the difference that instead of the oxdiazole mentioned 1,5-diphenyl-3-p-methoxyphenyl-pyrazoline according to DE-AS 10 60 714, corresponding to US Pat. No. 3,180,729, and instead of the polybutyl methacrylate and Polymethyl methacrylate a terpolymer of styrene, hexyl methacrylate and methacrylic acid in a molar ratio of 10:60:30 was used.
  • the coating was carried out on roughened and anodized aluminum support material in a layer thickness of about 6 g / m 2 .
  • the layer was treated with a dry developer after charging and imagewise exposure. After fixing, it was possible to remove the base coat with a commercially available decoating solution.
  • the offset printing plate obtained showed a high resolution and, in a printing test, gave good printing qualities up to a print run of well over 100,000.
  • Example 3 The procedure was as in Example 3, with the difference that instead of the pyrazoline, 4-methoxy benzaldehyde-diphenylhydrazone (DE-OS 32 46 036) and instead of Hostapermorange GR as dye N, N '- (3-methoxypropyl) perylene-tetracarboxylic acid-3,4,9,10-diimide ( R Paliogen-schwarz, BASF AG) has been used.
  • Example 2 The procedure was as in Example 1, with the difference that the layer was applied to the substrate with a layer thickness of 20 g / m 2 .
  • Example 3 The procedure was as in Example 3, with the difference that instead of the anodized aluminum support copper-clad polyimide film was used.
  • the coated film obtained in this way could be stripped perfectly after the imaging and fixing of the toner image at the areas not covered by toner.
  • High-quality, flexible printed circuit boards were obtained by etching away the metal areas underneath.
  • a layer of 25% by weight of Hostapermorange GR and 75% by weight of the terpolymer from Example 3 with a layer weight of 3 g / m 2 was first applied to anodized aluminum supports.
  • a top coat of 25% by weight of Hostapermorange GR, 20% by weight of 2,5-bis- (4-diethylaminophenyl) -oxdiazole-1,3,4 and 55% by weight of the terpolymer was coated on this underlayer with a layer weight of 3 g / m 2 applied.
  • a primer (undercoat) of 6 g / m 2 was applied to an anodized aluminum support.
  • the dried layer was then treated with a solution of 5% by weight of 2,5-bis (4-diethylaminophenyl) oxodiazole-1,3,4 in tetrahydrofuran and dried again.
  • Analogous results can be achieved by treating the still wet primer with an oxdiazole solution (wet-on-wet coating).
  • the material thus obtained had a high degree of flexibility with good adhesion of the layer to the support. Even when used in cyclic copiers, it showed no change in the electrophotographic properties with the number of charging and exposure cycles.
  • Example 2 The procedure was as in Example 2, with the difference that a polyurethane ( R Desmolac 2100, Bayer AG) was used instead of the terpolymer.
  • a polyurethane R Desmolac 2100, Bayer AG
  • Example 2 The procedure was as in Example 2, with the difference that Hostapermscharlach GO (Formula IV, C.I. 59 300) was used as pigment.
  • Hostapermscharlach GO Form IV, C.I. 59 300
  • a charge transport layer from the following solution was applied to this charge carrier-generating layer, dry layer weight likewise 3 g / m 2 : 50 g of a copolymer of styrene and maleic anhydride and 50 g of 2,5-bis (4-diethylaminophenyl) oxdiazole-1 , 3,4 were dissolved in 700 g of tetrahydrofuran and 250 g of butyl acetate with the addition of 0.1 g of silicone oil.
  • a monolayer with a layer weight of 6 g / m 2 from the following dispersion was applied to a roughened and anodized aluminum printing plate support: 6.25 g of Hostapermorange GR and 4.2 g of the terpolymer from Example 3 were in 50 g of tetrahydrofuran by grinding in a ball mill for 2 hours dispersed or dissolved and then added to a solution of 50 g of 2,5-bis (4-diethylaminophenyl) -oxdiazole-1,3,4, 40 g of the terpolymer from Example 3 and 0.1 g of silicone oil in 850 g of tetrahydrofuran .
  • This example corresponds to a sensitive monolayer formulation described in US Pat. No. 3,879,200.
  • Example 3 The procedure was as in Example 3, with the difference that instead of the methacrylate terpolymer, a likewise aqueous-alkaline decoatable sulfonyl urethane (prepared according to DE-OS 32 10 577, Example 1) was used.
  • Example 2 The procedure was as in Example 2, with the difference that cellulose nitrate with a degree of nitration of 12.2% was used instead of the methacrylates.
  • Example 3 The procedure was as in Example 3, with the difference that instead of the trans-Perinon Hostapermorange GR, the analog cis compound Permanent-red TG01 from Hoechst AG (C.I. 71.110) was used.
  • E l / 2 , E l / 4 , and E l / 8 mean the exposure energies that have to be applied at a light intensity of 3 / uW / cm 2 in order to discharge from -400 V to -200 V, -100 V or -50 V to reach.

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  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Health & Medical Sciences (AREA)
  • Emergency Medicine (AREA)
  • Photoreceptors In Electrophotography (AREA)
  • Hybrid Cells (AREA)
  • Light Receiving Elements (AREA)
  • Steroid Compounds (AREA)
EP85105785A 1984-05-15 1985-05-10 Matériau d'enregistrement électrophotographique Expired - Lifetime EP0161648B2 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AT85105785T ATE29603T1 (de) 1984-05-15 1985-05-10 Elektrophotographisches aufzeichnungsmaterial.

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19843417951 DE3417951A1 (de) 1984-05-15 1984-05-15 Elektrophotographisches aufzeichnungsmaterial
DE3417951 1984-05-15

Publications (3)

Publication Number Publication Date
EP0161648A1 true EP0161648A1 (fr) 1985-11-21
EP0161648B1 EP0161648B1 (fr) 1987-09-09
EP0161648B2 EP0161648B2 (fr) 1993-11-03

Family

ID=6235859

Family Applications (1)

Application Number Title Priority Date Filing Date
EP85105785A Expired - Lifetime EP0161648B2 (fr) 1984-05-15 1985-05-10 Matériau d'enregistrement électrophotographique

Country Status (11)

Country Link
US (1) US4668600A (fr)
EP (1) EP0161648B2 (fr)
JP (1) JPS60254142A (fr)
AT (1) ATE29603T1 (fr)
AU (1) AU574626B2 (fr)
BR (1) BR8502270A (fr)
CA (1) CA1259517A (fr)
DE (2) DE3417951A1 (fr)
ES (1) ES8607576A1 (fr)
FI (1) FI851884L (fr)
ZA (1) ZA853586B (fr)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0214596A2 (fr) * 1985-09-11 1987-03-18 Hoechst Aktiengesellschaft Procédé de fabrication de plaques d'impression
EP0356993A2 (fr) * 1988-08-31 1990-03-07 Canon Kabushiki Kaisha Procédé de formation d'images
EP0393787A2 (fr) * 1989-04-21 1990-10-24 Agfa-Gevaert N.V. Matériau enregistreur électrophotographique
EP0430235A2 (fr) * 1989-11-30 1991-06-05 Mita Industrial Co. Ltd. Elément photosensible électrophotographique

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JP2729616B2 (ja) * 1986-10-17 1998-03-18 富士ゼロックス株式会社 電子写真感光体
US5273853A (en) * 1989-06-13 1993-12-28 Mita Industrial Co., Ltd. Black photoconductive toner having sensitivity to light in the wavelength range of semiconductor lasers
JPH03146957A (ja) * 1989-11-02 1991-06-21 Iwatsu Electric Co Ltd 電子写真製版用印刷版
US5069992A (en) * 1989-11-17 1991-12-03 Fuji Photo Film Co., Ltd. Electrophotographic printing plate precursor containing alkali-soluble polyurethane resin as binder resin
JP2717584B2 (ja) * 1989-11-17 1998-02-18 富士写真フイルム株式会社 電子写真式製版用印刷原版
US5225307A (en) * 1992-01-31 1993-07-06 Xerox Corporation Processes for the preparation of photogenerating compositions
JP2944296B2 (ja) 1992-04-06 1999-08-30 富士写真フイルム株式会社 感光性平版印刷版の製造方法
US5266429A (en) * 1992-12-21 1993-11-30 Eastman Kodak Company Polyester-imides in electrophotographic elements
US5900342A (en) * 1996-04-26 1999-05-04 Eastman Kodak Company Photoconductive element having an outermost layer of a fluorinated diamond-like carbon and method of making the same
US6593046B2 (en) 2000-05-19 2003-07-15 Heidelberger Druckmaschinen Ag Photoconductive elements having a polymeric barrier layer
US6294301B1 (en) 2000-05-19 2001-09-25 Nexpress Solutions Llc Polymer and photoconductive element having a polymeric barrier layer
US6866977B2 (en) 2000-05-19 2005-03-15 Eastman Kodak Company Photoconductive elements having a polymeric barrier layer
US6194110B1 (en) * 2000-07-13 2001-02-27 Xerox Corporation Imaging members
US7270927B2 (en) * 2004-11-15 2007-09-18 Xerox Corporation Non-halogenated polymeric binder

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DE3026653A1 (de) * 1979-07-13 1981-01-15 Ricoh Kk Elektrophotographisches element
DE3110960A1 (de) * 1981-03-20 1982-09-30 Basf Ag, 6700 Ludwigshafen Elektrophotographisches aufzeichnungsmaterial
DE3227475A1 (de) * 1981-08-03 1983-02-17 Polychrome Corp., 10702 Yonkers, N.Y. In waessrigen mitteln loesliche oder dispergierbare, photoleitende masse

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0214596A2 (fr) * 1985-09-11 1987-03-18 Hoechst Aktiengesellschaft Procédé de fabrication de plaques d'impression
EP0214596A3 (fr) * 1985-09-11 1990-02-07 Hoechst Aktiengesellschaft Procédé de fabrication de plaques d'impression
EP0356993A2 (fr) * 1988-08-31 1990-03-07 Canon Kabushiki Kaisha Procédé de formation d'images
EP0356993A3 (fr) * 1988-08-31 1991-03-20 Canon Kabushiki Kaisha Procédé de formation d'images
EP0393787A2 (fr) * 1989-04-21 1990-10-24 Agfa-Gevaert N.V. Matériau enregistreur électrophotographique
EP0393787A3 (en) * 1989-04-21 1990-11-07 Agfa-Gevaert Naamloze Vennootschap Electrophotographic recording material
EP0430235A2 (fr) * 1989-11-30 1991-06-05 Mita Industrial Co. Ltd. Elément photosensible électrophotographique
EP0430235A3 (en) * 1989-11-30 1991-10-16 Mita Industrial Co. Ltd. Electrophotographic photosensitive element

Also Published As

Publication number Publication date
EP0161648B2 (fr) 1993-11-03
FI851884A0 (fi) 1985-05-13
BR8502270A (pt) 1986-01-14
ES8607576A1 (es) 1986-06-01
CA1259517A (fr) 1989-09-19
ZA853586B (en) 1985-12-24
AU574626B2 (en) 1988-07-07
FI851884L (fi) 1985-11-16
ES543034A0 (es) 1986-06-01
ATE29603T1 (de) 1987-09-15
DE3560608D1 (en) 1987-10-15
US4668600A (en) 1987-05-26
EP0161648B1 (fr) 1987-09-09
AU4251385A (en) 1985-11-21
DE3417951A1 (de) 1985-11-21
JPS60254142A (ja) 1985-12-14

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