EP0275108B1 - Farbentwicklungsblatt für druckempfindliche Aufzeichnungen und Farbentwicklungsmittel hierfür - Google Patents

Farbentwicklungsblatt für druckempfindliche Aufzeichnungen und Farbentwicklungsmittel hierfür Download PDF

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Publication number
EP0275108B1
EP0275108B1 EP88100475A EP88100475A EP0275108B1 EP 0275108 B1 EP0275108 B1 EP 0275108B1 EP 88100475 A EP88100475 A EP 88100475A EP 88100475 A EP88100475 A EP 88100475A EP 0275108 B1 EP0275108 B1 EP 0275108B1
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EP
European Patent Office
Prior art keywords
acid
colour developing
metal salt
colour
aromatic carboxylic
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
EP88100475A
Other languages
German (de)
English (en)
French (fr)
Other versions
EP0275108A2 (de
EP0275108A3 (en
Inventor
Hiroaki Central Research Laboratory Umeda
Mamoru Central Research Laboratory Suzuki
Akira Hasegawa
Kunio Hata
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.)
Nippon Paper Industries Co Ltd
Original Assignee
Nippon Paper Industries Co Ltd
Jujo Paper Co Ltd
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
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Application filed by Nippon Paper Industries Co Ltd, Jujo Paper Co Ltd filed Critical Nippon Paper Industries Co Ltd
Publication of EP0275108A2 publication Critical patent/EP0275108A2/de
Publication of EP0275108A3 publication Critical patent/EP0275108A3/de
Application granted granted Critical
Publication of EP0275108B1 publication Critical patent/EP0275108B1/de
Anticipated expiration legal-status Critical
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Classifications

    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
    • B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
    • B41M5/00—Duplicating or marking methods; Sheet materials for use therein
    • B41M5/124—Duplicating or marking methods; Sheet materials for use therein using pressure to make a masked colour visible, e.g. to make a coloured support visible, to create an opaque or transparent pattern, or to form colour by uniting colour-forming components
    • B41M5/132—Chemical colour-forming components; Additives or binders therefor
    • B41M5/155—Colour-developing components, e.g. acidic compounds; Additives or binders therefor; Layers containing such colour-developing components, additives or binders
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S428/00—Stock material or miscellaneous articles
    • Y10S428/914—Transfer or decalcomania
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/27—Web or sheet containing structurally defined element or component, the element or component having a specified weight per unit area [e.g., gms/sq cm, lbs/sq ft, etc.]
    • Y10T428/273—Web or sheet containing structurally defined element or component, the element or component having a specified weight per unit area [e.g., gms/sq cm, lbs/sq ft, etc.] of coating
    • Y10T428/277—Cellulosic substrate

Definitions

  • the present invention relates to a color developing sheet and color developing agent for pressure-sensitive recording medium, in which the disadvantages which a polyvalent metal salt of an aromatic carboxylic acid still has as a color developing agent are eliminated.
  • Pressure sensitive recording sheets are known as carbonless copy papers. When using mechanical pressure or impact pressure when writing or typing on a typewriter, they produce a colored impression and thus allow the simultaneous production of several copies. A colored image is formed due to the color development reaction between an electron donating colorless dye and an electron accepting color developing agent.
  • Typical color developing agents are inorganic solid acids such as activated clay, attapulgite, etc. (described in USP 2712507); substituted phenols and diphenols (described in Japanese Patent Publication 9309/1965); p-subst. phenol-formaldehyde polymers (described in Japanese Patent Publication 20144/1967); Metal salts of aromatic carboxylic acids (described in Japanese Patent Publications 10856/1974 and 1327/1977, etc.); 2,2'-bis-phenol sulfone compounds (described in JP-OS 10 6313/1979 etc.).
  • inorganic solid acids such as activated clay, attapulgite, etc. (described in USP 2712507); substituted phenols and diphenols (described in Japanese Patent Publication 9309/1965); p-subst. phenol-formaldehyde polymers (described in Japanese Patent Publication 20144/1967); Metal salts of aromatic carboxylic acids (described in Japanese Patent Publications 108
  • EP-A-271 081 (prior art under Article 54 (3) EPC) describes color developing agents for pressure-sensitive recording sheets and recording sheets containing this agent.
  • the color developing agent contains a reaction product of a carboxylated terpene phenol resin, an aromatic carboxylic acid and a compound of a polyvalent metal. It can be used in admixture with an inorganic solid acid, a phenol formaldehyde novolak resin, a substituted phenol resin, a metal salt thereof or a metal salt of an aromatic carboxylic acid.
  • EP-A-218 810 (prior art under Article 54 (3) EPC for all contracting states except IT) describes a color developing agent for a pressure-sensitive recording sheet and a color developing sheet containing this agent.
  • the color developing agent contains a polyvalent metal salt of a carboxy-terpene phenol resin, which is obtainable by condensing a cyclic monoterpene with phenol in the presence of an acid catalyst, carboxylating the condensed product and then reacting this product with a polyvalent metal or metal salt.
  • the color developing agent can be used in admixture with an inorganic solid acid, a phenol formaldehyde novolak salt, a substituted phenolic resin, a metal salt thereof or a metal salt of an aromatic carboxylic acid.
  • polyvalent metal salts of an aromatic carboxylic acid such as 3,5-di ( ⁇ -methylbenzyl) salicylic acid zinc salt are commonly used because they give a color developing sheet with superior durability of the colored image to the effects of light, moisture, heat and plasticizer.
  • the color development sheet containing a polyvalent metal salt of an aromatic carboxylic acid has the disadvantages that the color development speed and final color development intensity are not satisfactory.
  • the invention has for its object to provide a color developing agent for pressure-sensitive recording sheets which is largely free from the above disadvantages, i.e. has a superior color development speed and an improved intensity of final color development ("final color development intensity").
  • the inventors surprisingly found after many studies that polyvalent metal salts of an aromatic carboxylic acid in combination with a polyvalent metal salt of a carboxylated terpene phenolic resin and / or a reaction product of a carboxylated terpene phenolic resin, an aromatic carboxylic acid and a compound of a polyvalent metal have a superior color development speed and an improved final color development intensity and that the great fastness is retained as an advantage of using a polyvalent metal salt of the aromatic carboxylic acid.
  • the invention therefore relates to the color developing agents defined in claims 1 and 2.
  • the metal salts of aromatic carboxylic acids used in this invention are those of the following carboxylic acids: 3-methyl-5-tert-butylsalicylic acid, 3,5-di-tert-butylsalicylic acid, 5-nonylsalicylic acid, 5-cyclohexylsalicylic acid, 3-cyclohexylsalicylic acid, 3,5-diamylsalicylic acid, 5-cumylsalicylic acid, 3-tert-butyl-5-butyl methylbenzylsalicylic acid or 3,5-di ( ⁇ -methylbenzyl) salicylic acid and as an additive a polyvalent metal salt of a carboxylated terpene phenol resin and / or a reaction product of a carboxylated terpene phenol resin, an aromatic carboxylic acid and a polyvalent metal compound.
  • Typical examples of the polyvalent metals of the metal salts of aromatic carboxylic acids are magnesium, aluminum, cadmium, calcium, titanium, zinc, nickel, cobalt, manganese, vanadium, etc .; Magnesium, aluminum and zinc are preferred; Zinc is most preferred.
  • the color developing agents of the present invention have better yellowing resistance depending on the tent and superior plasticizer resistance.
  • the carboxylated terpene phenol resin is prepared as described in EP-A-218 810 by the following procedure.
  • cyclic monoterpene and phenol is carried out in a suitable solvent, for example a petroleum product. in the presence of an acidic catalyst, for example aluminum trichloride, boron trifluoride, sulfuric acid, polyphosphoric acid, etc., to obtain a condensation product.
  • an acidic catalyst for example aluminum trichloride, boron trifluoride, sulfuric acid, polyphosphoric acid, etc.
  • Typical examples of the cyclic monoterpene are pinene, limonene, terpinolene, menthadiene, gum turpentine oil, which contains ⁇ -pinene as the main component, dipentene, which contains ⁇ -limonene as the main component, and so on.
  • Typical examples of the phenol are monophenols, e.g. carbolic acid, alkylphenol, alkoxyphenol, halogenated phenol, etc .; and polyhydric phenols, for example resorcinol, pyrocatechol etc.
  • suitable solvents are benzene, toluene, xylenes, n-hexane, n-heptane, halogenated solvents, for example dichloromethane, chloroform, trichloromethane, bromobenzene and the like.
  • the condensation product is made alkaline by adding alkali metal, alkali metal hydroxide or carbonate and is introduced at 140-180 ° C and 5-30 atm with introduction of carbon dioxide gas. treated in an autoclave (Kolbe-Schmitt reaction), the carboxy group being introduced into the condensation product.
  • the solvent is distilled away. After cooling to room temperature, the product is washed out to remove the unreacted compounds. The product is further extracted with a dilute basic aqueous solution and then neutralized, whereby the carboxylated terpene phenol resin is excreted. The resin obtained is filtered off and washed out in order to obtain the purified carboxylated terpene phenol resin.
  • the polyvalent metal salt of a carboxylated terpene phenol resin is prepared by reacting a carboxylated terpene phenol resin with a polyvalent metal oxide, hydroxide, chloride, carbonate, sulfate or the like in the presence of an inorganic ammonium salt with melting, or a carboxylated terpene phenol resin with alkali metal hydroxide in one Solvents such as water, alcohol, etc. dissolve, add and react with a polyvalent metal salt, or the like.
  • polyvalent metals examples include magnesium, aluminum, calcium, cadmium, titanium, zinc, nickel, cobalt, manganese, etc .; Magnesium, aluminum and zinc are preferred. Zinc is most preferred.
  • the reaction product between the above carboxylated Terpene phenolic resin, aromatic carboxylic acid and polyvalent metal compound is prepared by uniformly mixing the carboxylated terpene phenolic resin, aromatic carboxylic acid and polyvalent metal compound and then reacting with each other, or by mixing two of the above three ingredients and then with one other component can react.
  • Uniform mixing is achieved by dissolving these ingredients in a solvent with stirring, or melting with heating, or by using other methods.
  • solvents are alkaline aqueous solutions such as sodium hydroxide, potassium hydroxide, sodium carbonate, etc .; and organic solvents such as alcohol, acetone, etc .; and the mixture of them.
  • aromatic carboxylic acid (monocyclic or polycyclic) is one in which the carboxy group is bonded directly to the ring.
  • aromatic carboxylic acid are: benzoic acid, p-hydroxybenzoic acid, chlorobenzoic acid, bromobenzoic acid, nitrobenzoic acid, methoxybenzoic acid, ethoxybenzoic acid, Toluic acid, ethylbenzoic acid, pn-propylbenzoic acid, p-isopropylbenzoic acid, 3-methyl-4-hydroxybenzoic acid, 3-ethyl-4-hydroxybenzoic acid, 3-methoxy-4-hydroxybenzoic acid, p-tert-butylbenzoic acid, o-benzoylbenzoic acid, p -benzoic acid, p -benzoic acid, p -benzoic acid, p -benzoic acid, p -benzoic acid, p -benzoic acid, p -benz
  • carboxylic acids Of these carboxylic acids, the monocarboxylic acids are preferred.
  • Suitable polyvalent metal compounds are oxides, halides, carbonates, sulfates, nitrates, acetates, formats, oxalates, benzoates, acetylacetone salts and salicylates of magnesium, aluminum, Cadmium, calcium, titanium, zinc, nickel, cobalt, manganese, vanadium, etc .; Magnesium, aluminum and zinc compounds are preferred; Zinc compounds are most preferred.
  • the amount of the polyvalent metal salt of a terpene phenol resin and / or the reaction product of a carboxylated terpene phenol resin, an aromatic carboxylic acid and a compound of a polyvalent metal based on the metal salt of an aromatic carboxylic acid is not particularly limited, and is preferably at least 1% by weight, more preferably at least 30% by weight.
  • a color developing sheet is prepared by applying the coating slip obtained above as a simple layer on a substrate.
  • multi-layer coating methods can also be used, in which case a coating composition containing a color developing agent is first applied to a substrate and then another coating composition containing another color developing agent, and the like.
  • the color developing agents of the present invention are used in all fields related to pressure sensitive recording sheets.
  • Pressure sensitive recording sheets e.g. have a middle sheet, lower sheet, single recording sheet, etc., or in which the color developing agent of the present invention is coated on or mixed with the support material;
  • Test means for a leuco dye after dissolving in an organic solvent Spot printing ink mixed with a wax; pressure sensitive ink using the color developing agent and / or microcapsules containing the leuco dye.
  • the coating slip according to the invention is produced by mixing kaolin clay, calcium carbonate, treatment starch, polyvinyl alcohol, synthetic or natural latex etc. and imparting the mixture with suitable viscosity and spreadability. It is advantageous to use 10-70% by weight of color developing agent, based on the total solids in the coating slip. With less than 10% by weight of color developing agent, the color developing ability is insufficient, with more than 70% by weight of color developing agent, on the other hand, the surface properties of the color developing sheet deteriorate.
  • color development layer it is also advantageous to apply the color development layer to a support in a coating amount of at least 0.5 g / m2, preferably 1.0-10.0 g / m2.
  • the color developing agent of the present invention is suitable for many known dyes used in pressure sensitive recording sheets.
  • Triphenylmethane series dyes such as crystal violet lactone, malachite green lactone, 3-dimethylaminotriphenylmethanephthalide, etc .
  • Fluoran series dyes such as 3,6-dimethoxyfluorane, 3-N-cyclohexylamino-6-chlorofluorane, 3-diethylamino-6-methyl-7-chlorofluorane, 1,2-benzo-6-dimethylaminofluorane, 1,2-benzo- ( 2'-diethylamino) -6-diethylamino-fluoran, 3-diethylamino-7-dibenzylamino-fluoran, 3-diethylamino-6-methyl-7-dibenzylamino-fluoran, 3-diethylamino-5-methyl-7-dibenzylamino-fluoran, 3-diethylamino-7-anilino-fluoran, 3-diethy
  • the invention is illustrated by the following examples and comparative examples.
  • the method of manufacturing a transfer sheet in which microcapsules containing the pressure sensitive dye were coated on a sheet of fine paper, and the evaluation method of the color development sheet using the transfer sheet is as follows.
  • dilution water 90 parts was mixed with 90 parts of a 10% aqueous solution of ethylene-maleic anhydride copolymer (trade name EMA, manufactured by Monsanto Co.). 10 parts of urea and 1 part of resorcinol were dissolved in this mixed solution, then the pH of the solution was adjusted to 3.4.
  • EMA ethylene-maleic anhydride copolymer
  • an oil mixture of alkyl diphenylethane (trade name: Hisol SAS 296, manufactured by Nisseki Kogaku Co.) and diisopropylnaphthalene (trade name KMC-113, manufactured by Kureka Kogaku Co.) was prepared in a weight ratio of 1: 1.
  • the core substance to be encapsulated there were prepared: (a) an oil of a blue color developing pressure sensitive dye by dissolving 3% crystal violet lactone and 1% benzoyl leucomethylene blue in the above oil mixture; and (b) an oil of a black color developing pressure sensitive dye by dissolving 5% 3-diethylamino-6-methyl-7-anilinofluorane, 1% 3-diethylamino-6-methyl-7-diphenylmethylaminofluorane and 0.5% 3-diethylamino-6-methyl-7-chlorofluorane in the above oil mixture.
  • a coating composition 180 parts of capsule slurry, 35 parts of wheat starch and 85 parts of an 8% aqueous oxidized starch solution were mixed to prepare a coating composition.
  • the coating composition was applied in a coating amount of 4.5 g / m2 on a base paper of 45 g / m2 and dried. In this way, two transfer sheets, that is, (A) a transfer paper developing blue color, and (B) a transfer paper developing a black color.
  • a CB sheet in which a support is coated with a microcapsule containing pressure-sensitive dye and a color developing sheet in which a support is coated with a color developing agent are laid so that the coated surfaces of the sheets touch each other.
  • a color image is generated with the grid plate roll calender.
  • the reflectance of the sheet is measured with a Hunter reflectometer (D-type; from Toyo Seiki Co.) measured using an amber filter.
  • the color development speed (J1 or J2) is calculated from the reflectance I0 before the color development, the reflectance I1 of 10 seconds after the color development or the reflectance I2 of 24 hours after the color development.
  • J 2nd I. 0 - I 2nd I. 0 x 100 (%) Higher color development speed and intensity of final color development are desirable.
  • Terpene phenolic resin was made from ⁇ -pinene and carbolic acid. 60 parts of 3,5-di ( ⁇ -methylbenzyl) salicylic acid zinc salt, 40 parts of carboxylated terpene phenol resin, 3.5 parts of sodium polyacrylate and 150 parts of water were mixed with one another and dispersed to an average particle size of the solid constituents of 3 ⁇ m by means of a sanding machine to give such a suspension.
  • a coating composition of the following formulation was made using the above suspension.
  • suspension 40 parts Calcium carbonate 100 parts Styrene butadiene latex (concentration: 40%) 15 parts Oxidized starch 15 parts water 415 pieces
  • the coating mass was applied with a Meyer stick Paper of 50 g / m2 basis weight was applied so that the amount of coating composition applied after drying was 5.5 g / m2.
  • a reaction product was prepared from a carboxylated terpene phenolic resin (using gum turpentine and carbolic acid), salicylic acid and zinc chloride in place of the carboxylated terpene phenolic zinc salt of Example 1.
  • a color developing agent suspension, a coating material and a color developing sheet were prepared from the obtained reaction product as in Example 1.
  • a carboxylated terpene phenolic resin was produced from ⁇ -pinene and carbolic acid. 40 parts of 3,5- ( ⁇ -methylbenzyl) salicylic acid zinc salt, 55 parts of the carboxylated terpene phenol resin zinc salt obtained, 2.5 parts of sodium hexametaphosphate and 180 parts of water were sand-dispersed to an average particle size of 2.5 ⁇ m by a color developing agent suspension to form a color developing agent suspension to build. A coating composition and a color developing sheet were prepared from the obtained color developing agent suspension in the same manner as in Example 1.
  • a color developing sheet was prepared using 3,4-di-tert-butlysalicylic acid zinc salt in the same manner as in Comparative Example 1.
  • the color development sheet the color development layer of which contains a metal salt of an aromatic carboxylic acid in combination with a carboxylated terpene phenolic resin zinc salt and / or a reaction product of a carboxylated terpene phenolic resin, an aromatic carboxylic acid and a zinc compound, has a superior color development speed and an improved final color development intensity compared to a color developing sheet containing only a polyvalent metal salt of an aromatic carboxylic acid.
  • the invention exhibits both a superior color development rate (color development speed) and an improved final color development intensity while maintaining the superior fastness of the color image as an advantage of the color development sheet containing a metal salt of aromatic carboxylic acids as a color developing agent.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Color Printing (AREA)
EP88100475A 1987-01-16 1988-01-14 Farbentwicklungsblatt für druckempfindliche Aufzeichnungen und Farbentwicklungsmittel hierfür Expired - Lifetime EP0275108B1 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP7529/87 1987-01-16
JP62007529A JPS63176176A (ja) 1987-01-16 1987-01-16 感圧複写紙用顕色シ−ト

Publications (3)

Publication Number Publication Date
EP0275108A2 EP0275108A2 (de) 1988-07-20
EP0275108A3 EP0275108A3 (en) 1988-09-14
EP0275108B1 true EP0275108B1 (de) 1996-05-22

Family

ID=11668307

Family Applications (1)

Application Number Title Priority Date Filing Date
EP88100475A Expired - Lifetime EP0275108B1 (de) 1987-01-16 1988-01-14 Farbentwicklungsblatt für druckempfindliche Aufzeichnungen und Farbentwicklungsmittel hierfür

Country Status (5)

Country Link
US (1) US4833119A (enrdf_load_stackoverflow)
EP (1) EP0275108B1 (enrdf_load_stackoverflow)
JP (1) JPS63176176A (enrdf_load_stackoverflow)
CA (1) CA1285765C (enrdf_load_stackoverflow)
DE (1) DE3855303D1 (enrdf_load_stackoverflow)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE68919409T2 (de) * 1988-08-09 1995-06-22 Nippon Petrochemicals Co Ltd Druckempfindliches kopiermaterial.
JPH02243384A (ja) * 1989-03-17 1990-09-27 Sumitomo Durez Co Ltd 感圧記録紙用顕色剤
JPH02255375A (ja) * 1989-03-29 1990-10-16 Arakawa Chem Ind Co Ltd 感圧記録体用顕色剤、顕色剤の水性分散液およびその製造法
EP0459942B1 (de) * 1990-05-10 1995-02-22 Ciba-Geigy Ag Tinten
US5261953A (en) * 1990-05-10 1993-11-16 Ciba-Geigy Corporation Inks
US6124377A (en) * 1998-07-01 2000-09-26 Binney & Smith Inc. Marking system
KR100689578B1 (ko) * 2003-02-28 2007-03-02 마츠시타 덴끼 산교 가부시키가이샤 화장실장치
US7815723B2 (en) * 2006-04-19 2010-10-19 Crayola Llc Water-based ink system
US7727319B2 (en) * 2006-04-19 2010-06-01 Crayola Llc Water-based ink system
GB2586188B (en) 2013-11-25 2021-06-23 Crayola Llc Marking system

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Publication number Priority date Publication date Assignee Title
FR2315003A1 (fr) * 1975-06-18 1977-01-14 Laprade Bernard Dispositif de regulation du melange air-carburant des moteurs a combustion interne
FR2315004A1 (fr) * 1975-06-18 1977-01-14 Laprade Bernard Dispositif de regulation du melange air-carburant des moteurs a combustion interne
JPS60159540A (ja) * 1984-01-30 1985-08-21 Matsushita Electric Ind Co Ltd 換気装置
US4546365A (en) * 1984-05-23 1985-10-08 Appleton Papers Inc. Record member
US4540998A (en) * 1984-05-23 1985-09-10 Appleton Papers Inc. Record member
US4573063A (en) * 1984-05-23 1986-02-25 Appleton Papers Inc. Record member
US4620874A (en) * 1984-06-28 1986-11-04 Btl Specialty Resins Corporation Metal modified phenolic resin color developers
JPS6219486A (ja) * 1985-07-19 1987-01-28 Jujo Paper Co Ltd 感圧複写紙用顕色剤及び顕色シ−ト

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
PAPER MANUFG. CO., LTD) 20-07-1973 *

Also Published As

Publication number Publication date
CA1285765C (en) 1991-07-09
EP0275108A2 (de) 1988-07-20
JPS63176176A (ja) 1988-07-20
EP0275108A3 (en) 1988-09-14
DE3855303D1 (de) 1996-06-27
US4833119A (en) 1989-05-23
JPH0466195B2 (enrdf_load_stackoverflow) 1992-10-22

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