DE669960T1 - Verbesserte hochtemperaturstabilitätaufweisende polyharnstoffpolymere sowie verfahren zu deren herstellung. - Google Patents
Verbesserte hochtemperaturstabilitätaufweisende polyharnstoffpolymere sowie verfahren zu deren herstellung.Info
- Publication number
- DE669960T1 DE669960T1 DE0669960T DE93925059T DE669960T1 DE 669960 T1 DE669960 T1 DE 669960T1 DE 0669960 T DE0669960 T DE 0669960T DE 93925059 T DE93925059 T DE 93925059T DE 669960 T1 DE669960 T1 DE 669960T1
- Authority
- DE
- Germany
- Prior art keywords
- polyurea
- polymers
- groups
- based liquid
- polyepoxide
- 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.)
- Pending
Links
- 229920000642 polymer Polymers 0.000 title claims abstract 13
- 238000000034 method Methods 0.000 title claims abstract 10
- 238000004519 manufacturing process Methods 0.000 title claims 2
- 229920002396 Polyurea Polymers 0.000 claims abstract 12
- 239000000203 mixture Substances 0.000 claims abstract 8
- 229920001228 polyisocyanate Polymers 0.000 claims abstract 8
- 239000005056 polyisocyanate Substances 0.000 claims abstract 8
- 238000009472 formulation Methods 0.000 claims abstract 4
- 229920000768 polyamine Polymers 0.000 claims abstract 4
- 229920000647 polyepoxide Polymers 0.000 claims abstract 4
- 238000011417 postcuring Methods 0.000 claims abstract 3
- 238000010438 heat treatment Methods 0.000 claims abstract 2
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 claims 4
- 239000007788 liquid Substances 0.000 claims 4
- VPKDCDLSJZCGKE-UHFFFAOYSA-N carbodiimide group Chemical group N=C=N VPKDCDLSJZCGKE-UHFFFAOYSA-N 0.000 claims 2
- OMXAWIAIGXKAQA-UHFFFAOYSA-N 1-(2-tert-butylphenyl)-2,2-dimethylpropane-1,1-diamine Chemical compound CC(C)(C)C1=CC=CC=C1C(N)(N)C(C)(C)C OMXAWIAIGXKAQA-UHFFFAOYSA-N 0.000 claims 1
- PISLZQACAJMAIO-UHFFFAOYSA-N 2,4-diethyl-6-methylbenzene-1,3-diamine Chemical compound CCC1=CC(C)=C(N)C(CC)=C1N PISLZQACAJMAIO-UHFFFAOYSA-N 0.000 claims 1
- 229930185605 Bisphenol Natural products 0.000 claims 1
- 239000004604 Blowing Agent Substances 0.000 claims 1
- 239000004606 Fillers/Extenders Substances 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 229920000538 Poly[(phenyl isocyanate)-co-formaldehyde] Polymers 0.000 claims 1
- 125000003277 amino group Chemical group 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 claims 1
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 claims 1
- 125000003700 epoxy group Chemical group 0.000 claims 1
- 239000000945 filler Substances 0.000 claims 1
- 239000003063 flame retardant Substances 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 239000004611 light stabiliser Substances 0.000 claims 1
- 239000000463 material Substances 0.000 claims 1
- -1 molding aids Substances 0.000 claims 1
- 238000000465 moulding Methods 0.000 claims 1
- 229920005862 polyol Polymers 0.000 claims 1
- 150000003077 polyols Chemical class 0.000 claims 1
- 238000010107 reaction injection moulding Methods 0.000 claims 1
- 230000003014 reinforcing effect Effects 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 239000000758 substrate Substances 0.000 claims 1
- 239000004094 surface-active agent Substances 0.000 claims 1
- MFVFDTCSVFBOTL-UHFFFAOYSA-N 1,3-diazetidine Chemical compound C1NCN1 MFVFDTCSVFBOTL-UHFFFAOYSA-N 0.000 abstract 1
- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical group O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 abstract 1
- 241000551547 Dione <red algae> Species 0.000 abstract 1
- 239000004593 Epoxy Substances 0.000 abstract 1
- 230000000704 physical effect Effects 0.000 abstract 1
Classifications
-
- 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
- C08G18/83—Chemically modified polymers
- C08G18/831—Chemically modified polymers by oxygen-containing compounds inclusive of carbonic acid halogenides, carboxylic acid halogenides and epoxy halides
-
- 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
- C08G18/30—Low-molecular-weight compounds
- C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
-
- 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
- C08G18/30—Low-molecular-weight compounds
- C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
- C08G18/3225—Polyamines
-
- 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
- C08G18/4009—Two or more macromolecular compounds not provided for in one single group of groups C08G18/42 - C08G18/64
- C08G18/4045—Mixtures of compounds of group C08G18/58 with other macromolecular compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
- C08L75/02—Polyureas
-
- 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
- C08G2120/00—Compositions for reaction injection moulding processes
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Polyurethanes Or Polyureas (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Epoxy Resins (AREA)
Claims (1)
- Europäische Patentanmeldung
Nr. 93 925 059.3
Dow Chemical Company-EU 12315P EP-WOPatentansprüche1. Verfahren zum Herstellen eines Polyharnstoffpolymers, umfassend das Mischen eines Polyisocyanats, eines Polyepoxids und eines Polyamins und Erhitzen des Gemischs, wobei das Verfahren einen ersten Schritt des Mischens einer Polyharnstofformulierung, umfassend:(A) ein Polyisocyanat,(B) ein Polyepoxid,(C) ein Polyaminbei einer Temperatur von weniger als 13O0C unter Reaktionsbedingungen, die ausreichend sind, um ein Polyharnstoffpolymer zu bilden und einen zweiten Schritt des Nachhärtens des Polyharnstoffpolymers bei einer Temperatur von größer als 15O0C aufweist,worin das Polyisocyanat ausgewählt ist aus der Gruppe, bestehend aus TDI, IVIDI, PMDI, auf TDI basierenden flüssigen Polyisocyanaten mit Uretonimingruppen, auf MDI basierenden flüssigen Polyisocyanaten mit Uretonimingruppen, auf TDI basierenden flüssigen Polyisocyanaten mit Carbodiimidgruppen, auf MDI basierenden flüssigen Polyisocyanaten mit Carbodiimidgruppen, MDI-Präpolymeren und Gemischen davon.2. Verfahren nach Anspruch 1, worin das Mischen im ersten Schritt mittels einer Reaktionsspritzgußvorrichtung durchgeführt wird.3.Verfahren nach Anspruch 2, worin das aromatische PolyaminDiethyltoluoldiamin oder di-tert-Butyltoluoldiamin ist.4. Verfahren nach Anspruch 3, worin das Polyepoxid ein Diglycidylether eines zweiwertigen Bisphenols ist.5. Verfahren nach Anspruch 4, worin diePolyharnstofformulierung auch eine Polyolbasis, ein aktiven Wasserstoff enthaltendes Material mit niederem Molekulargewicht oder Gemische davon umfaßt.Ö.Verfahren nach Anspruch 5, worin die Polyharnstofformulierung auch Treibmittel, Füllmittel, Verstärkungssubsträte, Formhilfsmittel, oberflächenaktive Mittel, Molekulargewichtextender, Ultraviolett-Licht-Stabilisatoren, Flammschutzmittel oder Gemische davon umfaßt.7. Verfahren nach Anspruch 1, worin das Verhältnis von Epoxidgruppen zu Amingruppen von 0,05 bis 1,50 ist.8. Polyharnstoffpolymer, umfassend ein nach dem Verfahren von Anspruch 1 hergestelltes Polymer.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US97956092A | 1992-11-20 | 1992-11-20 | |
PCT/US1993/010262 WO1994012573A1 (en) | 1992-11-20 | 1993-10-26 | Polyurea polymers having improved high temperature stability and method of making same |
Publications (1)
Publication Number | Publication Date |
---|---|
DE669960T1 true DE669960T1 (de) | 1996-02-29 |
Family
ID=25526962
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE0669960T Pending DE669960T1 (de) | 1992-11-20 | 1993-10-26 | Verbesserte hochtemperaturstabilitätaufweisende polyharnstoffpolymere sowie verfahren zu deren herstellung. |
DE69320827T Expired - Lifetime DE69320827T2 (de) | 1992-11-20 | 1993-10-26 | Verbesserte hochtemperaturstabilitätaufweisende polyharnstoffpolymere sowie verfahren zu deren herstellung |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE69320827T Expired - Lifetime DE69320827T2 (de) | 1992-11-20 | 1993-10-26 | Verbesserte hochtemperaturstabilitätaufweisende polyharnstoffpolymere sowie verfahren zu deren herstellung |
Country Status (10)
Country | Link |
---|---|
US (1) | US5525681A (de) |
EP (1) | EP0669960B1 (de) |
KR (1) | KR100300507B1 (de) |
AT (1) | ATE170540T1 (de) |
AU (1) | AU669409B2 (de) |
BR (1) | BR9307484A (de) |
CA (1) | CA2149888C (de) |
DE (2) | DE669960T1 (de) |
MX (1) | MX9307248A (de) |
WO (1) | WO1994012573A1 (de) |
Families Citing this family (23)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
ATE208706T1 (de) * | 1997-03-14 | 2001-11-15 | Dow Chemical Co | Nachhärtungsverfahren für reaktionseinspritzgeformte polyurethane |
AU4692799A (en) * | 1998-06-18 | 2000-01-05 | Mackinac Group, Inc., The | Method for damping noise, vibration and harshness of a substrate and compositiontherefor |
CA2393667C (en) * | 1999-12-10 | 2010-01-26 | The Dow Chemical Company | Blister-resistant molded polyurea polymer and method of making a blister-resistant molded polyurea polymer |
JP2004508998A (ja) * | 2000-09-11 | 2004-03-25 | ダウ グローバル テクノロジーズ インコーポレイティド | 補強部材により形成された、ランフラットタイヤ支持体及びフィラメント |
WO2002022378A2 (en) * | 2000-09-11 | 2002-03-21 | Dow Global Technologies Inc. | Method and device for preparing a tire support |
WO2002068131A1 (en) * | 2001-02-17 | 2002-09-06 | Hehr International Inc. | Polyamine-epoxide adduct and polyurea prepared therefrom |
US6765080B2 (en) | 2002-06-06 | 2004-07-20 | Bayer Corporation | High performance RIM elastomers and a process for their production |
US6861499B2 (en) * | 2003-02-24 | 2005-03-01 | Triton Systems, Inc. | Branched polyphosphonates that exhibit an advantageous combination of properties, and methods related thereto |
US20040167283A1 (en) * | 2003-02-24 | 2004-08-26 | Michael Vinciguerra | Linear polyphosphonates that exhibit an advantageous combination of properties, and methods related thereto |
KR101020164B1 (ko) | 2003-07-17 | 2011-03-08 | 허니웰 인터내셔날 인코포레이티드 | 진보된 마이크로전자적 응용을 위한 평탄화 막, 및 이를제조하기 위한 장치 및 방법 |
US7560525B2 (en) * | 2004-04-02 | 2009-07-14 | Frx Polymers, Llc | Crystalline polyphosphonates and methods related thereto |
US7569717B2 (en) * | 2005-07-19 | 2009-08-04 | Frx Polymers, Llc | Diaryl alkylphosphonates and method for preparing same |
US7645850B2 (en) * | 2005-08-11 | 2010-01-12 | Frx Polymers, Inc. | Poly(block-phosphonato-ester) and poly(block-phosphonato-carbonate) and methods of making same |
US7666932B2 (en) * | 2005-10-17 | 2010-02-23 | Frx Polymers, Inc. | Compositions comprising polyphosphonates and additives that exhibit an advantageous combination of properties, and methods related thereto |
WO2007079272A2 (en) * | 2005-10-18 | 2007-07-12 | Frx Polymers Llc | Diaryl alkylphosphonates and methods for preparing same |
US7838604B2 (en) * | 2005-12-01 | 2010-11-23 | Frx Polymers, Inc. | Method for the production of block copolycarbonate/phosphonates and compositions therefrom |
US7790907B2 (en) * | 2006-07-21 | 2010-09-07 | Basf Corporation | Method of producing a uretonimine-modified isocyanate composition |
US20080085987A1 (en) * | 2006-10-05 | 2008-04-10 | Thomas Savino | Method of producing a uretonimine-modified isocyanate composition |
JP4562753B2 (ja) * | 2007-06-28 | 2010-10-13 | 住化バイエルウレタン株式会社 | 屋内外施設用常温硬化性表面仕上げ材 |
US7928259B2 (en) * | 2008-02-12 | 2011-04-19 | Frx Polymers, Inc. | Diaryl alkylphosphonates and methods for preparing same |
US9487654B2 (en) | 2011-12-29 | 2016-11-08 | Certainteed Corporation | Foam, composition, and method |
JP6330196B2 (ja) * | 2012-10-24 | 2018-05-30 | コンパニー ゼネラール デ エタブリッスマン ミシュラン | 金属をゴムに接着させるための接着プライマーとして特に有用であるポリ尿素 |
JP2016510355A (ja) | 2013-01-22 | 2016-04-07 | エフアールエックス ポリマーズ、インク. | リン含有エポキシ化合物およびそれからなる組成物 |
Family Cites Families (28)
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US1436890A (en) * | 1920-07-19 | 1922-11-28 | B B Mfg And Drilling Company | Well-drilling apparatus |
US3494888A (en) * | 1966-08-30 | 1970-02-10 | Wilbur R Mcelroy | Resin compositions from polyepoxides and isocyanate polymers |
US3639338A (en) * | 1968-05-06 | 1972-02-01 | Gen Mills Inc | Reactive polyureas process of preparing same and use thereof in curing epoxy resins |
ZA708090B (en) * | 1969-12-30 | 1971-08-25 | Goodyear Tire & Rubber | Cured polyurethane compositions containing epoxy resins |
JPS538354B2 (de) * | 1974-02-15 | 1978-03-28 | ||
DE2446438C2 (de) * | 1974-09-28 | 1985-04-11 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von Oxazolidingruppen enthaltenden Urethanen und ihre Verwendung |
FR2351139A1 (fr) * | 1976-05-14 | 1977-12-09 | Hitachi Ltd | Composition de resines polymerisable, thermodurcissable |
US4218543A (en) * | 1976-05-21 | 1980-08-19 | Bayer Aktiengesellschaft | Rim process for the production of elastic moldings |
US4204051A (en) * | 1976-06-05 | 1980-05-20 | Bayer Aktiengesellschaft | Process for polyurethanes from ortho-ester-blocked polyols |
US4144211A (en) * | 1977-09-06 | 1979-03-13 | The Dow Chemical Company | Novel complexes of polyoxazolines or polyoxazines and halogens, interhalogens or pseudo-halogens and process for preparing same |
US4272618A (en) * | 1979-04-30 | 1981-06-09 | Texaco Development Corp. | Heat stable reaction injection molded elastomers |
US4225460A (en) * | 1979-06-28 | 1980-09-30 | Minnesota Mining And Manufacturing Company | Latent Lewis acid catalyst system and process |
US4237252A (en) * | 1979-06-28 | 1980-12-02 | Minnesota Mining And Manufacturing Company | Heat activatable one-part liquid resin systems |
US4374209A (en) * | 1980-10-01 | 1983-02-15 | Interchem International S.A. | Polymer-modified polyols useful in polyurethane manufacture |
DE3323122A1 (de) * | 1983-06-27 | 1985-05-23 | Siemens AG, 1000 Berlin und 8000 München | Verfahren zur herstellung von reaktionsharzformstoffen |
DE3323153A1 (de) * | 1983-06-27 | 1985-01-03 | Siemens AG, 1000 Berlin und 8000 München | Hitzehaertbare reaktionsharzmischungen |
US4542165A (en) * | 1983-09-08 | 1985-09-17 | Sanyo Chemical Industries, Ltd. | Polyurethane based on epoxy-containing polymer polyol and process for making the same |
DE3434270A1 (de) * | 1984-09-14 | 1986-03-20 | Siemens AG, 1000 Berlin und 8000 München | Heisshaertende reaktionsharzmischung zur impraegnierung von isolierungen elektrischer geraete und zur herstellung von formstoffen mit und ohne einlagen |
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US4814103A (en) * | 1988-02-18 | 1989-03-21 | Mobay Corporation | Color stable urethane prepolymer |
DE3836598A1 (de) * | 1988-10-27 | 1990-05-03 | Bayer Ag | Reaktivsysteme und ein verfahren zur herstellung von polyurethankunststoffen |
US4906772A (en) * | 1988-12-02 | 1990-03-06 | Amoco Corporation | Process for production of polycarboxylic aromatic acids |
US5106943A (en) * | 1989-10-04 | 1992-04-21 | Takeda Chemical Industries, Ltd. | Resin compositions, shaped articles, and methods for manufacture |
DE4104199A1 (de) * | 1991-02-12 | 1992-08-13 | Basf Ag | Verfahren zur herstellung von polyurethan-elastomeren und hierfuer geeignete mischungen aus polyoxybutylen-polyoxyalkylen-glykolen und glycidylverbindungen |
-
1993
- 1993-10-26 WO PCT/US1993/010262 patent/WO1994012573A1/en active IP Right Grant
- 1993-10-26 AT AT93925059T patent/ATE170540T1/de not_active IP Right Cessation
- 1993-10-26 DE DE0669960T patent/DE669960T1/de active Pending
- 1993-10-26 KR KR1019950702024A patent/KR100300507B1/ko not_active IP Right Cessation
- 1993-10-26 DE DE69320827T patent/DE69320827T2/de not_active Expired - Lifetime
- 1993-10-26 EP EP93925059A patent/EP0669960B1/de not_active Expired - Lifetime
- 1993-10-26 AU AU54513/94A patent/AU669409B2/en not_active Ceased
- 1993-10-26 CA CA002149888A patent/CA2149888C/en not_active Expired - Lifetime
- 1993-10-26 BR BR9307484A patent/BR9307484A/pt not_active IP Right Cessation
- 1993-11-19 MX MX9307248A patent/MX9307248A/es not_active IP Right Cessation
-
1995
- 1995-04-13 US US08/420,993 patent/US5525681A/en not_active Expired - Lifetime
Also Published As
Publication number | Publication date |
---|---|
JPH08503518A (ja) | 1996-04-16 |
EP0669960A1 (de) | 1995-09-06 |
CA2149888A1 (en) | 1994-06-09 |
KR100300507B1 (ko) | 2001-11-05 |
ATE170540T1 (de) | 1998-09-15 |
AU5451394A (en) | 1994-06-22 |
CA2149888C (en) | 2003-12-23 |
AU669409B2 (en) | 1996-06-06 |
BR9307484A (pt) | 1999-08-24 |
DE69320827T2 (de) | 1999-01-21 |
MX9307248A (es) | 1994-06-30 |
KR950704421A (ko) | 1995-11-20 |
US5525681A (en) | 1996-06-11 |
JP3537821B2 (ja) | 2004-06-14 |
DE69320827D1 (de) | 1998-10-08 |
EP0669960B1 (de) | 1998-09-02 |
WO1994012573A1 (en) | 1994-06-09 |
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