EP0445953B1 - Mit kationischem Polymer modifizierter Füllstoff, Verfahren zu seiner Herstellung und seine Verwendung in der Papierherstellung - Google Patents

Mit kationischem Polymer modifizierter Füllstoff, Verfahren zu seiner Herstellung und seine Verwendung in der Papierherstellung Download PDF

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EP0445953B1
EP0445953B1 EP91301574A EP91301574A EP0445953B1 EP 0445953 B1 EP0445953 B1 EP 0445953B1 EP 91301574 A EP91301574 A EP 91301574A EP 91301574 A EP91301574 A EP 91301574A EP 0445953 B1 EP0445953 B1 EP 0445953B1
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Prior art keywords
filler
dimer
filler material
acid
cationic polymer
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EP0445953A1 (de
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Robert A. Gill
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Minerals Technologies Inc
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Minerals Technologies Inc
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    • D—TEXTILES; PAPER
    • D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
    • D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
    • D21H17/00—Non-fibrous material added to the pulp, characterised by its constitution; Paper-impregnating material characterised by its constitution
    • D21H17/63—Inorganic compounds
    • D21H17/67—Water-insoluble compounds, e.g. fillers, pigments
    • D21H17/675—Oxides, hydroxides or carbonates
    • D—TEXTILES; PAPER
    • D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
    • D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
    • D21H21/00—Non-fibrous material added to the pulp, characterised by its function, form or properties; Paper-impregnating or coating material, characterised by its function, form or properties
    • D—TEXTILES; PAPER
    • D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
    • D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
    • D21H17/00—Non-fibrous material added to the pulp, characterised by its constitution; Paper-impregnating material characterised by its constitution
    • D21H17/03—Non-macromolecular organic compounds
    • D21H17/05—Non-macromolecular organic compounds containing elements other than carbon and hydrogen only
    • D21H17/17—Ketenes, e.g. ketene dimers
    • D—TEXTILES; PAPER
    • D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
    • D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
    • D21H17/00—Non-fibrous material added to the pulp, characterised by its constitution; Paper-impregnating material characterised by its constitution
    • D21H17/20—Macromolecular organic compounds
    • D21H17/33—Synthetic macromolecular compounds
    • D21H17/46—Synthetic macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • D21H17/54—Synthetic macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen
    • D21H17/55—Polyamides; Polyaminoamides; Polyester-amides
    • D—TEXTILES; PAPER
    • D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
    • D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
    • D21H17/00—Non-fibrous material added to the pulp, characterised by its constitution; Paper-impregnating material characterised by its constitution
    • D21H17/63—Inorganic compounds
    • D21H17/67—Water-insoluble compounds, e.g. fillers, pigments
    • D21H17/68—Water-insoluble compounds, e.g. fillers, pigments siliceous, e.g. clays
    • D—TEXTILES; PAPER
    • D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
    • D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
    • D21H17/00—Non-fibrous material added to the pulp, characterised by its constitution; Paper-impregnating material characterised by its constitution
    • D21H17/63—Inorganic compounds
    • D21H17/67—Water-insoluble compounds, e.g. fillers, pigments
    • D21H17/69—Water-insoluble compounds, e.g. fillers, pigments modified, e.g. by association with other compositions prior to incorporation in the pulp or paper

Definitions

  • This invention broadly relates to the field of surface treated inorganic compounds. More particularly, the invention relates to the provision of compositions suitable for use as a papermaking filler material wherein an inorganic base filler material is surface treated with a substance which enhances the performance of the filler in the papermaking process. The invention also relates to a method for improving the papermaking process, especially by reducing the requirement for sizing material and for improving the characteristics of paper produced according to the process.
  • internal sizing The purpose of internal sizing is to impart resistance to liquid penetration to the sheet. Internal sizing, along with sheet porosity (which is controlled at the size press), controls ink penetration in printing and writing papers, along with binder migration in coating basestock.
  • the sizing of alkaline papers with cellulose reactive sizing agents or "synthetic sizes" has been established for more than 30 years. Two synthetic sizes presently in commercial use, alkyl ketene dimer (AKD) and alkenyl succinic anhydride (ASA), impart sizing to the sheet by means of a chemical reaction (covalent bonding) with the hydroxyl groups of cellulose fiber.
  • US 2,865,743 discloses a sizing composition comprising silica particles with a ketene dimer deposited on the surface.
  • the composition is prepared by dispersing a ketene dimer or mixture of ketene dimers on a carrier comprising finely-divided amorphous silica to form a free-flowing powder in which the particles of silica contain a deposit or coating of the ketene dimer.
  • PCC precipitated calcium carbonate
  • Fig. 1 is a plot of Hercules size measurement versus filler content for handsheets containing modified and unmodified fillers.
  • Fig. 2 is a plot of water pick-up as measured by the Cobb size test versus filler content for handsheets containing modified and unmodified fillers.
  • Fig. 3 is a plot of Hercules size measurement versus filler content for handsheets containing modified filler at various levels of polymer treatment.
  • Fig. 4 is a plot of Hercules size measurement versus filler content for handsheets containing modified and unmodified fillers at different sizing levels.
  • Fig. 5 is a plot of sheet opacity versus filler content for handsheets containing modified and unmodified fillers.
  • Fig. 6 is a plot of sheet opacity versus sheet tensile strength for handsheets containing modified and unmodified fillers.
  • Fig. 7 is a plot of sheet brightness versus filler content for handsheets containing modified and unmodified fillers.
  • Fig. 8 is a plot of Hercules size measurement versus filler content for sheets containing modified and unmodified fillers made on a pilot papermachine.
  • Fig. 9 is a plot of water pick-up as measured by the Cobb size test versus filler content for sheets containing modified and unmodified fillers made on a pilot papermachine.
  • Fig. 10 is a plot of corrected sheet opacity versus filler content for sheets containing modified and ummodified fillers made on a pilot papermachine.
  • Fig. 11 shows comparative microscopic photographs illustrating distribution of filler material for sheets containing modified and unmodified fillers made on a pilot papermachine.
  • Fig. 12 represents a three-dimensional plot of Hercules size measurement versus treatment temperature and percent cationic polymer treatment level at an 8% filler level in the handsheets.
  • Fig. 13 represents a three-dimensional plot of Hercules size measurement versus treatment temperature and percent cationic polymer treatment level at an 16% filler level in the handsheets.
  • Fig. 14 represents a three-dimensional plot of Hercules size measurement versus treatment temperature and percent cationic polymer treatment level at an 24% filler level in the handsheets.
  • the cationic polymers found to be most effective for surface treating the papermaking filler materials are dimers of the general formula: where R is a hydrocarbon group selected from the group consisting of alkyl with at least 8 carbon atoms, cycloalkyl with at least 6 carbon atoms, aryl, aralkyl and alkaryl.
  • dimers are octyl-, decyl-, dodecyl-, tetradecyl-, hexadecyl-, octadecyl-, eikosyl-, dokosyl-, tetrakosyl-, phenyl-, benzyl-beta-naphthyl-, and cyclohexyl- dimer.
  • the polymer is made cationic as a result of treating the dimer with a polyamino-amide and/or polyamine polymer reacted with an epoxidized halohydrin compound, such as epichlorohydrin, thereby forming tertiary and quaternary amine groups on the dimer surface. It is preferred that the cationic charge on the dimer be derived primarily from quaternary amine groups.
  • a polymer material of this type is manufactured by and is commercially available from Hercules, Inc., Wilmington, DE, under the tradename Hercon.
  • filler materials such as titanium dioxide, talc and silica/silicate pigments, which if used untreated have a detrimental effect on sizing, are utilizable when treated with a cationic polymer material of the aforesaid type according to the present invention.
  • the temperature at which the filler material is treated with the cationic polymer is also a significant parameter in determining the extent to which the sizing demand of the polymer-treated filler is reduced.
  • treatment of the aqueous slurry containing the filler material with the cationic polymer is done at a temperature of from about 5 to 70°C.
  • the preferred treatment temperature range is from about 20 to 30°C, and the most preferred treatment temperature is at about 25°C.
  • the pH of the aqueous slurry containing the filler material has an effect on treatment.
  • the slurry should not be at a pH greater than 10 at the time of the treatment.
  • the filler material treated with the cationic polymer should also subsequently be stored at a pH not greater than 10 to prevent decomposition of the cationic polymer coating which occurs at pH's greater than about 10.
  • Comparative Formax Noble and Wood handsheets (60 g/m2 or 40 lbs./3300 ft2) were prepared from a furnish consisting of 75% bleached hardwood and 25% bleached softwood Kraft pulps beaten to 400 Canadian Standard Freeness (CSF) at pH 7.0 in distilled water. A high molecular weight, medium charge density, cationic polyacrylamide (PAM) retention aid was used at 0.05%. Synthetic sizing agents (AKD or ASA) were added at levels from 0.10% to 0.30%. Several fillers were used, including various polymer-modified PCC fillers to test the effect of the polymer treatment against unmodified PCC and fine ground limestone (FGL).
  • the fillers were added to the furnish at 20% solids to achieve 8%, 16%, 24% and 40% filler in the finished sheets.
  • a blank, containing no filler was prepared and tested. Distilled water was used throughout the handsheet process.
  • the sheets were conditioned at 50% RH and 23°C and tested for grammage, percent filler, HST, Cobb size, opacity, brightness, caliper, tensile, and porosity. Scattering coefficients were determined using the appropriate reflectance values and Kubelka-Munk equations. Elemental mapping of the filler distribution in the sheet, both in the XY plane and in the Z-directional plane, was performed using a scanning electron microscope (SEM) with elemental analysis capabilities.
  • SEM scanning electron microscope
  • a secondary benefit derived from the modified fillers was an increase of one-half point in opacity without a subsequent loss in tensile strength or sheet brightness (Figs. 5, 6, and 7).
  • the increased opacity without loss of strength or brightness appears to be predominately due to the substantial increase in the cationic charge of the modified filler particles.
  • Increasing the cationic charge on the particles makes them adsorb more uniformly on the fiber surface and less between fiber crossings.
  • Scanning electron micrographs revealed better distribution of the filler in the sheet for the modified PCC fillers which supports improved optical performance.
  • Table II shows the relationship between the filler's specific surface area and polymer treatment level on sizing values.
  • a vacuum drainage jar apparatus was used to measure the retention and drainage characteristics of the fillers under conditions similar to an actual high-speed paper-machine.
  • the furnish was the same as used in Example 1 with the retention aid level evaluated at 0.05%.
  • the fillers were added so that a content of 16% +/- 1.0% would be retained in the final pad.
  • the stock (0.5% consistency) was agitated in a three vane jar at 750 rpm. Automatic control placed the contents of the jar under a vacuum of 10 kPa during initial drainage followed by 5 seconds of high vacuum (50 kPa).
  • the pad which formed was weighed and then dried and reweighed to yield percent sheet dryness values (these numbers predict the ease at which water is removed from the sheet). Percent filler retention was calculated from the amount of calcium carbonate in the fiber pad via X-ray fluorescence and the known amount added to the stock.
  • Improved papermachine runnability can be measured in many ways. Improved drainage on the wire along with increased sheet dryness off the couch provides the paper-maker with the opportunity to increase machine speed (increase production rate) and/or decrease steam consumption at the dryers (increased profitability). Improved filler retention without the need to use excessive amounts of retention aid enhances sheet quality which includes formation. This also leads to better runnability and economics from a cleaner wet end system. Retention and drainage results, shown in Table III, using a vacuum drainage jar revealed improved first pass filler retention for the modified PCC fillers.
  • Sheet dryness values were also improved over the untreated PCC filler, indicating better drainage.
  • the experiments were conducted under precise and well-controlled conditions in the laboratory, however these results are transferable to a papermachine leading to better wet end control with improved runnability, as is shown in Examples 3 and 4, following.
  • a pilot machine run was conducted utilizing a pilot scale papermachine.
  • a 60 g/m2 (40 lbs./3300 ft2) sheet was produced using the same furnish composition as in Examples 1 and 2.
  • the same cationic retention aid was utilized at 0.0125% and an AKD sizing agent was added at 0.15%.
  • Various calcium carbonate fillers i.e., untreated commercial PCC, untreated commercial FGL, 0.5 and 1.0 percent by weight cationic polymer-modified PCC's) were added to achieve levels of 8%, 16%, and 24% filler in the sheet.
  • the fillers were characterized with respect to particle size by gravity sedimentation analysis using a Micromeritics Sedigraph 5000D. Specific surface area was determined by the use of BET nitrogen adsorption analysis. Dry brightness was measured using a Hunter LabScan. Particle charge (zeta potential) was determined using doppler laser light scattering technique from a Coulter DELSA 440. Filler properties are listed in Table IV.
  • a mill trial was conducted utilizing a Fourdrinier papermachine running at 610 m/min (2000 fpm).
  • a 60 g/m (40 lbs/3300 ft) high opacity sheet was run with and without a modified PCC filler as part of the furnish composition.
  • the modified PCC filler was treated with 1.5 percent by weight of cationic polymer.
  • An anionic retention aid was utilized along with an ASA sizing agent. Both additives were held constant throughout the trial.
  • Handbox and white-water tray samples were obtained throughout the trial and analyzed for first pass filler retention and total retention.
  • the samples showed a minimum loss of sizing compared to typical commercially filled sheets.
  • the surface coefficient of friction of the sheets was also evaluated.
  • the surface coefficient of friction of the sheets is an important measure of the runnability of the paper through high-speed reprographic equipment.
  • the results of this evaluation are shown in Table VIII.
  • the polymer-modified PCC-filled sheets showed a better coefficient of friction of the sheet surface than the unmodified sheets.
  • a handsheet study was performed to evaluate the effect of filler treatment temperature, that is, the temperature at which the cationic polymer is applied to the filler material, on reduction in the sizing demand in the handsheets utilizing the cationic polymer-treated filler.
  • Treatment was at temperatures in the range of from 25-65°C.
  • Treatment was performed at levels of from 0 to 1.25 weight percent of cationic polymer.
  • the cationic polymer used was an alkyl ketene dimer, Hercon-85 (Hercules, Inc., Wilmington, DE).
  • the filler was a precipitated calcium carbonate (PCC) (Albacar HO, Pfizer, Inc., New York).
  • Filler loading in the handsheets was at several levels, of from 8 to 24 weight percent of treated filler.
  • Comparative Formax (Noble and Wood) handsheets (60 g/m2 or 40 lbs./3300 ft2) were prepared from a furnish blend consisting of 75% bleached hardwood and 25% bleached softwood Kraft pulps beaten to a consistency of 0.3125% and a Canadian Standard Freeness (CSF) of 400 ⁇ 25 at pH 7.0 in distilled water. Additional wet end additives included an alkyl ketene dimer size (Hercon-75, Hercules, Inc., Wilmington, DE) in an amount of 0.25 wt.
  • CSF Canadian Standard Freeness
  • Paper properties tested include size, opacity, pigment scattering coefficient and sheet brightness. Size was tested by the Hercules Size Test. Reported values are in seconds. Opacity was tested by the TAPPI test. Reported values are Corrected opacity, %. Sheet brightness was tested by the TAPPI test. Reported values are Brightness, %. The results are reported in Table X.

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  • Chemical & Material Sciences (AREA)
  • Inorganic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Dispersion Chemistry (AREA)
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Claims (6)

  1. Zusammensetzung, umfassend einen Füllstoff zur Papierherstellung, ausgewählt aus der Gruppe, bestehend aus feingemahlenem, natürlichem Calciumcarbonat aus Kalkstein, gefälltem Calciumcarbonat-, Ton-, Titandioxid-, Talc-, Silica/Silicat-Pigmenten sowie Kombinationen davon, welcher Füllstoff oberflächenbehandelt wurde mit etwa 0,1 bis etwa 10,0 Gewichtsprozent eines kationischen Polymers, bezogen auf die Trockenmasse des Füllstoffes, wobei das kationische Polymer ein Dimer der allgemeinen Formel ist:
    Figure imgb0015
     worin R eine Kohlenwasserstoffgrupppe ist, ausgewählt aus der Gruppe, bestehend aus Alkyl mit mindestens 8 Kohlenstoffatomen, Cycloalkyl mit mindestens 6 Kohlenstoffatomen, Aryl, Aralkyl und Alkaryl, und das Dimer kationisch gemacht wurde durch Behandlung mit mindestens einem Polyamin-Amid und einem Polyamin-Polymer, umgesetzt mit einer epoxidierten Halohydrin-Verbindung unter Bildung von tertiären und quaternären Amingruppen auf der Dimer-Oberfläche.
  2. Zusammensetzung nach Anspruch 1, bei welcher das Dimer ausgewählt wird aus der Gruppe, bestehend aus Octyl-, Decyl, Dodecyl-, Tetradecyl-, Hexadecyl-, Octadecyl-, Eicosyl-, Docosyl-, Tetracosyl-, Phenyl, Benzyl-beta-naphthyl und Cyclohexyl-Dimere; aus Montansäuren, Napthensäure, delta-9,10-Decylensäure, delta-9,10-Dodecylensäure, Palmitoleinsäure, Oleinsäure, Ricinolsäure, Linoleat, Linolsäure und Oleostearinsäure, hergestellte Dimere; und hergestellte Dimere aus natürlichen Fettsäuregemischen, wie sie aus Kokosnußöl, Babassuöl, Palmkernöl, Palmöl. Olivenöl, Erdnußöl, Rapsöl, Rinderfett und Schweinefett erhalten werden, sowie Mischungen der vorgenannten.
  3. Zusammensetzung nach Anspruch 1, bei welcher das epoxidierte Halohydrin Epichlohydrin ist.
  4. Verfahren zur Herstellung eines mit einem kationischen Polymer oberflächenbehandelten Füllstoffes zur Papierherstellung, welches verfahren umfaßt: Zusetzen von etwa 0,1 bis etwa 10,0 Gewichtsprozent eines kationischen Polymers, welches ein Dimer der allgemeinen Formel ist: worin R eine Kohlenwasserstoffgrupppe ist, ausgewählt aus der Gruppe, bestehend aus Alkyl mit mindestens 8 Kohlenstoffatomen, Cycloalkyl mit mindestens 6 Kohlenstoffatomen, Aryl, Aralkyl und Alkaryl, und das Dimer kationisch gemacht wurde durch Behandlung mit mindestens einem Polyamin-Amid und einem Polyamin-Polymer, umgesetzt mit einer epoxidierten Halohydrin-Verbindung unter Bildung von tertiären und quaternären Amingruppen auf der Dimer-Oberfläche; zu einer etwa 1 % bis etwa 76 % Feststoffe enthaltenden Füllstoff-Aufschlämmung, indem die Aufschlämmung unter Rühren bei einer Temperatur von etwa 5 °C bis etwa 70 °C und bei einem pH-Wert von weniger als etwa 10 gehalten wird, um das Füllstoffverhalten zu verbessern.
  5. Verfahren nach Anspruch 4, bei welchem die Menge des zur Aufschlämmung zugesetzten Polymers in direkter Beziehung zur Oberfläche des Füllstoffes steht.
  6. Verfahren zum Verbessern der Papierherstellung, indem mindestens eines der Ergebnisse zum Reduzieren der erforderlichen Leimungsmenge erzielt wird, Aufrechthalten des Leimungsgehaltes über die Zeit, Verbessern der Handhabungseigenschaften einer erzeugten Papierbahn, einschließlich Wasserabgabe, Verbessern der physikalischen Eigenschaften des resultierenden Papiers, einschließend Füllstoffretention, Füllstoffverteilung, Zugfestigkeit und Oberflächenreibungskoeffizient, sowie Verbessern der optischen Eigenschaften des resultierenden Papiers, einschließend Weißgrad, Opazität und Pigment-Streukoeffizient, welches Verfahren umfaßt: Zusetzen zu einem Eintrag für die Papierherstellung von etwa 5 % bis etwa 50 Gewichtsprozent Füllstoff, der oberflächenbehandelt wurde mit etwa 0,1 bis etwa 10,0 Gewichtsprozent eines kationischen Polymers, bezogen auf die Trockenmasse des Füllstoffes, wobei das kationische Polymer ein Dimer der allgemeinen Formel ist:
    Figure imgb0017
     worin R eine Kohlenwasserstoffgrupppe ist, ausgewählt aus der Gruppe, bestehend aus Alkyl mit mindestens 8 Kohlenstoffatomen, Cycloalkyl mit mindestens 6 Kohlenstoffatomen, Aryl, Aralkyl und Alkaryl, das kationisch gemacht wurde durch Behandlung mit mindestens einem Polyamin-Amid und einem Polyamin-Polymer, umgesetzt mit einer epoxidierten Halohydrin-Verbindung unter Bildung von tertiären und quaternären Amingruppen auf der Dimer-Oberfläche.
EP91301574A 1990-03-08 1991-02-27 Mit kationischem Polymer modifizierter Füllstoff, Verfahren zu seiner Herstellung und seine Verwendung in der Papierherstellung Expired - Lifetime EP0445953B1 (de)

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EP (1) EP0445953B1 (de)
JP (1) JP2528557B2 (de)
KR (1) KR940001536B1 (de)
AU (1) AU632403B2 (de)
BR (1) BR9100933A (de)
CA (1) CA2037525C (de)
DE (1) DE69112239T2 (de)
ES (1) ES2078436T3 (de)
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HK (1) HK1007778A1 (de)

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CN102660150B (zh) * 2012-04-28 2014-02-26 华南理工大学 一种改性碳酸钙填料及其制备方法与在湿强纸中的应用
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FR3001236B1 (fr) 2013-01-22 2015-06-26 Emin Leydier Composition aqueuse, pour la fabrication de supports fibreux en feuille a proprietes de resistance mecanique ameliorees, procede, utilisation, supports fibreux et articles manufactures associes
EP3018176B1 (de) 2014-11-07 2018-04-25 Omya International AG Verfahren zur herstellung von ausgeflockten füllstoffpartikeln
EP3018175B1 (de) 2014-11-07 2019-02-06 Omya International AG Verfahren zur Herstellung von ausgeflockten Füllstoffpartikeln
KR102608657B1 (ko) * 2021-06-07 2023-12-05 태경산업 주식회사 탈크를 포함하는 제지의 필러용 또는 코팅용 소재 및 이의 제조 방법

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Also Published As

Publication number Publication date
ES2078436T3 (es) 1995-12-16
FI911147A0 (fi) 1991-03-07
EP0445953A1 (de) 1991-09-11
FI102198B (fi) 1998-10-30
DE69112239T2 (de) 1996-05-02
AU632403B2 (en) 1992-12-24
AU7272791A (en) 1991-10-31
FI102198B1 (fi) 1998-10-30
HK1007778A1 (en) 1999-04-23
JP2528557B2 (ja) 1996-08-28
BR9100933A (pt) 1991-11-05
CA2037525C (en) 1995-10-31
CA2037525A1 (en) 1991-09-09
JPH05247886A (ja) 1993-09-24
DE69112239D1 (de) 1995-09-28
FI911147A (fi) 1991-09-09
KR910017026A (ko) 1991-11-05
KR940001536B1 (ko) 1994-02-23

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