WO1998055528A1 - Verfahren zur herstellung von geschlossenzelligen polyurethan-hartschaumstoffen mit geringer wärmeleitfähigkeit - Google Patents

Verfahren zur herstellung von geschlossenzelligen polyurethan-hartschaumstoffen mit geringer wärmeleitfähigkeit Download PDF

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Publication number
WO1998055528A1
WO1998055528A1 PCT/EP1998/003039 EP9803039W WO9855528A1 WO 1998055528 A1 WO1998055528 A1 WO 1998055528A1 EP 9803039 W EP9803039 W EP 9803039W WO 9855528 A1 WO9855528 A1 WO 9855528A1
Authority
WO
WIPO (PCT)
Prior art keywords
rigid polyurethane
polyurethane foams
weight
production
propylene oxide
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.)
Ceased
Application number
PCT/EP1998/003039
Other languages
German (de)
English (en)
French (fr)
Inventor
Torsten Heinemann
Werner Dietrich
Walter Klän
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.)
Bayer AG
Original Assignee
Bayer AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Bayer AG filed Critical Bayer AG
Priority to US09/424,093 priority Critical patent/US6306920B1/en
Priority to DE59802846T priority patent/DE59802846D1/de
Priority to AU79150/98A priority patent/AU7915098A/en
Priority to JP50141099A priority patent/JP4761591B2/ja
Priority to BRPI9809930-2A priority patent/BR9809930B1/pt
Priority to DK98929365T priority patent/DK0991686T3/da
Priority to AT98929365T priority patent/ATE211749T1/de
Priority to EP98929365A priority patent/EP0991686B1/de
Priority to SI9830080T priority patent/SI0991686T1/xx
Priority to CA002292510A priority patent/CA2292510C/en
Priority to HK00108560.3A priority patent/HK1029355B/xx
Publication of WO1998055528A1 publication Critical patent/WO1998055528A1/de
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J9/00—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
    • C08J9/04—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent
    • C08J9/12—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent by a physical blowing agent
    • C08J9/14—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent by a physical blowing agent organic
    • C08J9/141—Hydrocarbons
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/48—Polyethers
    • C08G18/4804—Two or more polyethers of different physical or chemical nature
    • C08G18/482—Mixtures of polyethers containing at least one polyether containing nitrogen
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J9/00—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
    • C08J9/04—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent
    • C08J9/12—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent by a physical blowing agent
    • C08J9/14—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent by a physical blowing agent organic
    • C08J9/143—Halogen containing compounds
    • C08J9/144—Halogen containing compounds containing carbon, halogen and hydrogen only
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2110/00—Foam properties
    • C08G2110/0025—Foam properties rigid
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2110/00—Foam properties
    • C08G2110/0041—Foam properties having specified density
    • C08G2110/005—< 50kg/m3
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2205/00—Foams characterised by their properties
    • C08J2205/10—Rigid foams
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2375/00—Characterised by the use of polyureas or polyurethanes; Derivatives of such polymers
    • C08J2375/04—Polyurethanes

Definitions

  • Rigid polyurethane foams are used due to their low thermal conductivity in the insulation of refrigerators and freezers, industrial plants, tank farms, pipelines, in shipbuilding and in the construction industry.
  • a comprehensive overview of the production of rigid polyurethane foams and their use can be found in the Plastics Manual, Volume 7 (Polyurethane), 2nd edition 1983, published by Dr. Günter Oertel (Carl Hanser Verlag, Kunststoff).
  • the thermal conductivity of a largely closed-cell rigid polyurethane foam is largely dependent on the type of blowing agent or cell gas used.
  • the fully halogenated chlorofluorocarbons (CFCs) had proven particularly suitable for this, in particular trichlorofluoromethane (Rl 1), which has a particularly low thermal conductivity. These substances are chemically inert and non-toxic.
  • fully halogenated chlorofluorocarbons enter the stratosphere due to their high stability, where their chlorine content contributes to the depletion of the ozone present there (Molina, Rowland, ⁇ ature 249 (1974) 810).
  • hydrofluoroalkanes such as e.g. R 141b (dichlorofluoroethane) to be used as a blowing agent (US Pat. No. 5,272,183).
  • the polyol formulation must be modified in order to
  • the object of the present invention was therefore to find a process for the production of closed-cell rigid polyurethane foams with low thermal conductivity, in which even when using different blowing agent systems
  • Cyclopentane / i-butane mixtures, cyclopentane / i-pentane mixtures, R 141 b, R 245 fa can be foamed and always give rigid polyurethane foams with a similarly low thermal conductivity and excellent property profile, which are particularly suitable for insulating refrigerators and freezers. This is particularly advantageous for the processor of such formulations, since in the case of one
  • Propellant change e.g. For legal reasons, no special adjustment of machine parameters and no change in storage is required, so that a propellant can be changed quickly and inexpensively
  • the invention relates to a method for producing closed-cell
  • Rigid polyurethane foams with low thermal conductivity made of polyols and polyisocyanates as well as blowing agents and optionally foam auxiliaries, thereby characterized in that the rigid polyurethane foam is obtained by reacting
  • blowing agents from the group of the alkanes, cycloalkanes, hydrofluorochlorohydrocarbons, hydrofluorocarbons and
  • auxiliaries and / or additives with B. an optionally modified polyisocyanate with an NCO content of 20 to 48 wt .-%.
  • Polyol formulations used in accordance with the invention contain one, at least two compounds which have isocyanate-reactive hydrogen atoms and have a molecular weight of 300 to 800 g / mol. They are obtained by polyaddition of alkylene oxides such as ethylene oxide, propylene oxide, butylene oxide, dodecyl oxide or styrene oxide, preferably propylene oxide or ethylene oxide onto starter compounds. Polyhydric alcohols such as sucrose and sorbitol and mixtures of these alcohols with water, glycerol, propylene glycol, ethylene glycol or diethylene glycol are used as starter compounds. By means of these polyols to be used according to the invention, the mechanical properties of the rigid polyurethane foams usually required in practice can be achieved.
  • Polyol formulations used according to the invention further contain at least one, at least two compounds containing hydrogen atoms which are reactive toward isocyanates and have a molecular weight of 300 to 800 g / mol, which are obtained by polyaddition of alkylene oxides such as ethylene oxide, propylene oxide, butylene oxide, dodecyl oxide or styrene oxide, preferably propylene oxide or ethylene oxide to aromatic mono-, di- or polyamines such as aniline, phenylenediamines, toluenediamines (2,3-toluenediamine, 3,4-toluenediamine, 2,4-toluenediamine, 2,5-toluenediamine, 2,6-toluenediamine or mixtures of the isomers mentioned), 2,2'-diaminodiphenylmethane, 2,4'-diaminodiphenylmethane, 4,4'-diaminodiphenylmethane or mixtures of
  • Polyol formulations used according to the invention further contain at least one, at least two compounds containing hydrogen atoms which are reactive toward isocyanates and have a molecular weight of 200 to 800 g / mol, which are obtained by polyaddition of alkylene oxides such as ethylene oxide, propylene oxide, butylene oxide, dodecyl oxide or styrene oxide, preferably propylene oxide or ethylene oxide onto aromatic compounds
  • Mono-, di- or polyamines such as ethylenediamine, oligomers of ethyl lendiamines (for example diethylenetriamine, triethylenenteramine or pentaethylene-hexamine), ethanolamine, diethanolamine, triethanolamine, N-methyl- or N-ethyl-diethanolamine, 1,3-propylenediamine, 1,3- or 1,4-butylenediamine, 1,2 -, 1,3-, 1,4-, 1,5-, 1,6-hexamethylene diamine.
  • Polyol formulations used according to the invention further contain one, at least two compounds having hydrogen atoms which are reactive toward isocyanates and have a molecular weight of 500 to 1500 g / mol. They are obtained by polyaddition of alkylene oxides such as ethylene oxide, propylene oxide, butylene oxide, dodecyl oxide or styrene oxide, preferably propylene oxide or ethylene oxide onto starter compounds such as water, propylene glycol, ethylene glycol or diethylene glycol.
  • alkylene oxides such as ethylene oxide, propylene oxide, butylene oxide, dodecyl oxide or styrene oxide, preferably propylene oxide or ethylene oxide onto starter compounds such as water, propylene glycol, ethylene glycol or diethylene glycol.
  • the catalysts customary in polyurethane chemistry can be used in the process according to the invention.
  • examples of such catalysts are: triethylene diamine, N, N-dimethylcyclohexylamine, tetramethylene diamine, 1-methyl-4-dimethylaminoethylpiperazine, triethylamine, tributylamine, dimethylbenzylamine, N, N ', N "tris (dimethylaminopropyl) hexahydrotriazine, Dimethylaminopropylformamide, N, N, N ', N'-tetramethylethylene diamine, N, N, N', N 'tetramethylbutane diamine, tetramethylhexanediamine, pentamethyldiethylenetriamine, tetramethyldiaminoethyl ether, dimethylpiperazine, 1,2-dimethylimidazole, l-aza , 3,0) octane, bis (
  • the polyol formulations used in the process according to the invention contain 0.5 to 7.0 parts by weight, preferably 1.0 to 3.0 parts by weight of water per 100 parts by weight
  • blowing agents from the group of the alkanes, in particular having 4 to 5 carbon atoms such as, for example, i-pentane, n-pentane, n-butane, isobutane, 2,2-dimethylbutane, or cycloalkanes, in particular cyclopentane or cyclohexane, or hydrofluorochlorine - Hydrocarbons, preferably R 141b (dichlorofluoroethane) or hydrofluorocarbons, preferably R 245fa, and mixtures of the blowing agents mentioned.
  • n 2 to 4 preferably 2
  • Q is an aliphatic hydrocarbon radical with 2 to 18, preferably 6 to 10,
  • Carbon atoms a cycloaliphatic hydrocarbon radical having 4 to 15, preferably 5 to 10, carbon atoms, an aromatic hydrocarbon radical having 8 to 15, preferably 8 to 13, carbon atoms, e.g. such polyisocyanates as described in DE-OS 28 32 253, pages 10 to 11.
  • the technically easily accessible polyisocyanates for. B. the 2,4- and 2,6-tolylene diisocyanate and any mixtures of these isomers (“TDI”), polyphenylpolymethylene polyisocyanates such as those produced by aniline-formaldehyde condensation and subsequent phosgenation (“crude MDI”) and carbodiimide groups, urethane groups, Polyisocyanates containing allophanate groups, isocyanurate groups, urea groups or biuret groups
  • Modified polyisocyanates in particular modified polyisocyanates, which differ from Derive 2,4- and 2,6-tolylene diisocyanate or from 4,4'- and / or 2,4'-diphenylmethane diisocyanate.
  • Prepolymers of the isocyanates mentioned and organic compounds with at least one hydroxyl group such as 1 to 4 hydroxyl-containing polyol or polyester components with a molecular weight of 60 to 1,400, can also be used.
  • Paraffins or fatty alcohols or dimethylpolysiloxanes as well as pigments or dyes, furthermore stabilizers against aging and weather influences, plasticizers and substances having a fististatic and bacteriostatic effect as well as fillers such as barium sulfate, diatomaceous earth, soot or sludge chalk can also be used.
  • the foam production is carried out in closed molds.
  • the reaction mixture is introduced into a mold.
  • Metal e.g. Aluminum
  • plastic e.g. Epoxy resin
  • the foamable reaction mixture foams in the mold and forms the shaped body.
  • the foam molding can be carried out so that the molded part has a cell structure on its surface. But it can also be carried out so that the molded part has a compact skin and a cellular core. According to the invention, one proceeds in the former case so much in the form
  • Foamable reaction mixture enters that the foam formed just fills the mold.
  • the way of working in the latter case is that there is more foamable reaction mixture is introduced into the mold than is necessary to fill the interior of the mold with foam.
  • “over-charging” is used.
  • Such a procedure is known, for example, from US Pat. Nos. 3,178,490 and 3,182,104
  • the method according to the invention is preferably used for the foaming of cavities in refrigerators and freezers.
  • foams can also be produced by block foaming or by the double transport method known per se
  • the rigid foams obtainable according to the invention are used, for example, in construction and for the insulation of district heating pipes and containers
  • the invention also relates to the use of the rigid foams produced according to the invention as an intermediate layer for composite elements and for foaming cavities in the Kuhlmobelhaus
  • Polyol A polypropylene oxide / ethylene oxide polyether with a molecular weight of 550 based
  • Polyol B polypropylene oxide / ethylene oxide polyether of molecular weight 560 based on a mixture of 2,3- and 3,4-toluenediamine
  • Polyol C polypropylene oxide polyether with a molecular weight of 540 based on ethylene diamine
  • Polyol D polypropylene oxide polyether with a molecular weight of 900 based on propylene glycol
  • the mixture of polyethers A - D becomes a mixture according to the invention
  • Silicone stabilizer commercially available silicone stabilizer from Goldschmidt AG, Essen
  • Examples 1 to 5 show that when the polyol formulation according to the invention is foamed with customary blowing agents, rigid foams with excellent practical properties are always obtained; this with a core density which is recognizable to the person skilled in the art.

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Polyurethanes Or Polyureas (AREA)
  • Manufacture Of Porous Articles, And Recovery And Treatment Of Waste Products (AREA)
PCT/EP1998/003039 1997-06-03 1998-05-22 Verfahren zur herstellung von geschlossenzelligen polyurethan-hartschaumstoffen mit geringer wärmeleitfähigkeit Ceased WO1998055528A1 (de)

Priority Applications (11)

Application Number Priority Date Filing Date Title
US09/424,093 US6306920B1 (en) 1997-06-03 1998-05-22 Method for producing closed-cell rigid polyurethane foams having low thermal conductivity
DE59802846T DE59802846D1 (de) 1997-06-03 1998-05-22 Verfahren zur herstellung von geschlossenzelligen polyurethan-hartschaumstoffen mit geringer wärmeleitfähigkeit
AU79150/98A AU7915098A (en) 1997-06-03 1998-05-22 Method for producing closed-cell rigid polyurethane foams having low thermal conductivity
JP50141099A JP4761591B2 (ja) 1997-06-03 1998-05-22 低熱伝導率を有する独立気泡ポリウレタン硬質フォームの製造方法
BRPI9809930-2A BR9809930B1 (pt) 1997-06-03 1998-05-22 processo para a preparaÇço de espumas rÍgidas de poliuretano de cÉlulas fechadas com baixa condutibilidade tÉrmica a partir de poliàis e poliisocianatos, bem como de agentes de esponjamento e, eventualmente, de auxiliares de esponjamento.
DK98929365T DK0991686T3 (da) 1997-06-03 1998-05-22 Fremgangsmåde til fremstilling af hårde polyurethanskumstoffer med lukkede celler og med lav varmeledningsevne
AT98929365T ATE211749T1 (de) 1997-06-03 1998-05-22 Verfahren zur herstellung von geschlossenzelligen polyurethan-hartschaumstoffen mit geringer wärmeleitfähigkeit
EP98929365A EP0991686B1 (de) 1997-06-03 1998-05-22 Verfahren zur herstellung von geschlossenzelligen polyurethan-hartschaumstoffen mit geringer wärmeleitfähigkeit
SI9830080T SI0991686T1 (en) 1997-06-03 1998-05-22 Method for producing closed-cell rigid polyurethane foams having low thermal conductivity
CA002292510A CA2292510C (en) 1997-06-03 1998-05-22 Method for producing closed-cell rigid polyurethane foams having low thermal conductivity
HK00108560.3A HK1029355B (en) 1997-06-03 1998-05-22 Method for producing closed-cell rigid polyurethane foams having low thermal conductivity

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19723193.4 1997-06-03
DE19723193A DE19723193A1 (de) 1997-06-03 1997-06-03 Verfahren zur Herstellung von geschlossenzelligen Polyurethan-Hartschaumstoffen mit geringer Wärmeleitfähigkeit

Publications (1)

Publication Number Publication Date
WO1998055528A1 true WO1998055528A1 (de) 1998-12-10

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PCT/EP1998/003039 Ceased WO1998055528A1 (de) 1997-06-03 1998-05-22 Verfahren zur herstellung von geschlossenzelligen polyurethan-hartschaumstoffen mit geringer wärmeleitfähigkeit

Country Status (16)

Country Link
US (1) US6306920B1 (enExample)
EP (1) EP0991686B1 (enExample)
JP (1) JP4761591B2 (enExample)
CN (1) CN1138804C (enExample)
AT (1) ATE211749T1 (enExample)
AU (1) AU7915098A (enExample)
BR (1) BR9809930B1 (enExample)
CA (1) CA2292510C (enExample)
DE (2) DE19723193A1 (enExample)
DK (1) DK0991686T3 (enExample)
ES (1) ES2171029T3 (enExample)
PT (1) PT991686E (enExample)
RU (1) RU2222549C2 (enExample)
SI (1) SI0991686T1 (enExample)
TR (1) TR199903017T2 (enExample)
WO (1) WO1998055528A1 (enExample)

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CN116731381A (zh) * 2023-05-16 2023-09-12 四川大学 一种含二氧化碳加合物的液态发泡剂

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US6846850B2 (en) * 2003-01-22 2005-01-25 Bayer Materialscience Llc Rigid polyurethane foams with improved properties
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US20050148677A1 (en) * 2003-12-30 2005-07-07 Elsken Kevin J. Low K-factor rigid foam systems
JP4736503B2 (ja) * 2004-03-31 2011-07-27 旭硝子株式会社 硬質発泡合成樹脂の製造方法
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EP3190133B1 (en) 2005-11-14 2024-10-23 Dow Global Technologies Llc Method of molding rigid polyurethane foams with enhanced thermal conductivity
JP5189254B2 (ja) * 2006-06-13 2013-04-24 アキレス株式会社 発泡樹脂断熱材
KR101522038B1 (ko) * 2007-01-12 2015-05-20 바스프 에스이 폴리우레탄 경질 발포체
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ES2672975T3 (es) * 2007-01-30 2018-06-19 Dow Global Technologies Llc Polioles iniciados con amina y espuma rígida de poliuretano obtenida a partir de ellos
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CN101357979B (zh) * 2008-08-20 2011-06-29 江苏科技大学 一种耐低温lng保温材料及其制备方法
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AT508870B1 (de) * 2009-09-16 2015-11-15 Alutechnik Matauschek Gmbh Isolierteil
CN103459451B (zh) * 2011-04-07 2015-06-10 巴斯夫欧洲公司 制备pu硬质泡沫材料的方法
WO2013017554A1 (de) * 2011-08-01 2013-02-07 Basf Se Hfo/wassergetriebene hartschaum-systeme
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CN107163219A (zh) * 2017-05-19 2017-09-15 美的集团股份有限公司 聚氨酯泡沫的发泡配方、制备方法和聚氨酯泡沫保温材料
CN107903366B (zh) * 2017-11-14 2019-08-30 美的集团股份有限公司 用于聚氨酯发泡的催化剂、聚氨酯发泡组合物及其发泡方法与应用
WO2019194966A1 (en) * 2018-04-03 2019-10-10 Dow Global Technologies Llc Foam formulations
US10640600B2 (en) * 2018-04-24 2020-05-05 Covestro Llc Rigid polyurethane foams suitable for use as panel insulation
CN113748150A (zh) * 2019-04-29 2021-12-03 科思创有限公司 适合用作板隔热材料的硬质聚氨酯泡沫
CN110305282A (zh) * 2019-07-04 2019-10-08 长虹美菱股份有限公司 一种负压发泡冰箱的隔热层配方及发泡工艺
US11685140B2 (en) * 2020-06-05 2023-06-27 Johns Manville Non-wicking underlayment board
US11773586B2 (en) * 2020-06-05 2023-10-03 Johns Manville Non-wicking underlayment board

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US6306920B1 (en) 2001-10-23
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DK0991686T3 (da) 2002-04-22
ATE211749T1 (de) 2002-01-15
JP2002502455A (ja) 2002-01-22
DE59802846D1 (de) 2002-02-28
BR9809930A (pt) 2000-08-01
TR199903017T2 (xx) 2000-05-22
DE19723193A1 (de) 1998-12-10
BR9809930B1 (pt) 2008-11-18
JP4761591B2 (ja) 2011-08-31
CA2292510A1 (en) 1998-12-10
RU2222549C2 (ru) 2004-01-27
SI0991686T1 (en) 2002-04-30
EP0991686A1 (de) 2000-04-12
EP0991686B1 (de) 2002-01-09
ES2171029T3 (es) 2002-08-16
AU7915098A (en) 1998-12-21
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PT991686E (pt) 2002-06-28

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