WO1990011309A1 - Compositions elastomeres de polyurethane lineaire et utilisation de diisocyanates modifies pour preparer de telles compositions - Google Patents

Compositions elastomeres de polyurethane lineaire et utilisation de diisocyanates modifies pour preparer de telles compositions Download PDF

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Publication number
WO1990011309A1
WO1990011309A1 PCT/US1990/001477 US9001477W WO9011309A1 WO 1990011309 A1 WO1990011309 A1 WO 1990011309A1 US 9001477 W US9001477 W US 9001477W WO 9011309 A1 WO9011309 A1 WO 9011309A1
Authority
WO
WIPO (PCT)
Prior art keywords
polyol
component
composition
diisocyanate
extender
Prior art date
Application number
PCT/US1990/001477
Other languages
English (en)
Inventor
Bert A. Ross
John R. Damewood
Original Assignee
Reeves Brothers, Inc.
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
Priority claimed from US07/326,183 external-priority patent/US5013811A/en
Priority claimed from US07/326,865 external-priority patent/US5001208A/en
Application filed by Reeves Brothers, Inc. filed Critical Reeves Brothers, Inc.
Priority to KR1019910701135A priority Critical patent/KR920701290A/ko
Publication of WO1990011309A1 publication Critical patent/WO1990011309A1/fr

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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
    • C08G18/08—Processes
    • C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
    • 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
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/80—Masked polyisocyanates
    • C08G18/8003—Masked polyisocyanates masked with compounds having at least two groups containing active hydrogen
    • C08G18/8006—Masked polyisocyanates masked with compounds having at least two groups containing active hydrogen with compounds of C08G18/32
    • C08G18/8038—Masked polyisocyanates masked with compounds having at least two groups containing active hydrogen with compounds of C08G18/32 with compounds of C08G18/3225
    • 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
    • C08G18/08—Processes
    • C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
    • C08G18/12—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step using two or more compounds having active hydrogen in the first polymerisation step
    • 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
    • C08G18/4018—Mixtures of compounds of group C08G18/42 with compounds of group C08G18/48
    • 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
    • C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
    • C08G18/66—Compounds of groups C08G18/42, C08G18/48, or C08G18/52
    • C08G18/6603—Compounds of groups C08G18/42, C08G18/48, or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38
    • C08G18/6607—Compounds of groups C08G18/42, C08G18/48, or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/3203
    • 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
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
    • C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
    • C08G18/7657—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings
    • C08G18/7664—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings containing alkylene polyphenyl groups
    • C08G18/7671—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings containing alkylene polyphenyl groups containing only one alkylene bisphenyl group
    • 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
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/80—Masked polyisocyanates
    • C08G18/8003—Masked polyisocyanates masked with compounds having at least two groups containing active hydrogen
    • C08G18/8006—Masked polyisocyanates masked with compounds having at least two groups containing active hydrogen with compounds of C08G18/32
    • C08G18/8009—Masked polyisocyanates masked with compounds having at least two groups containing active hydrogen with compounds of C08G18/32 with compounds of C08G18/3203
    • C08G18/8012—Masked polyisocyanates masked with compounds having at least two groups containing active hydrogen with compounds of C08G18/32 with compounds of C08G18/3203 with diols

Definitions

  • polyurethane elastomers which are considered top of the line with respect to performance, include, for example, polytetramethylene glycol (polyether) polyurethanes and poly(butane adipates or hexane adipates) ester polyurethanes.
  • polyether polytetramethylene glycol
  • poly(butane adipates or hexane adipates) ester polyurethanes include, for example, polytetramethylene glycol (polyether) polyurethanes and poly(butane adipates or hexane adipates) ester polyurethanes.
  • polyether polytetramethylene glycol
  • polyurethanes exhibit good hydrolytic stability and low temperature properties but are generally poor for fuel resistance and oxidation resistance, while the polyester polyurethanes are tough with good abrasion resistance, oxidation resistance and fuel resistance, but not
  • Japanese Patent Specification Sho(61)-151235 discloses the preparation of aliphatic polycarbonate polyols from various mixtures of dialkyl carbonates and glycols.
  • MDI Diphenyl methane diisocyanate
  • a liquid MDI composition can be prepared, for example, by partially reacting solid MDI with a glycol, diol or other polyol. Generally, about 10 to 35% of the isocyanate groups are reacted with the polyol.
  • a number of U.S. patents illustrate this concept, including U.S. Patents 3,883,571, 4,115,429, 4,118,411, 4,229,347, 4,490,300, 4,490,301, 4,539,156, 4,539,157 and 4,539,158.
  • Such liquid diisocyanates are stated as being useful for forming polyurethanes for a wide variety of applications. None of these modified diisocyanate compositions have, however, been utilized to prepare linear thermoplastic polyurethane elastomers which have lower temperature
  • a linear thermoplastic polyurethane elastomer composition prepared from a polyol component, a diisocyanate compound, and first and second extender components.
  • the processing temperature of the polyurethane is lowered by initially reacting the diisocyanate compound with the first extender in a molar ratio of above 2:1 to form a modified diisocyanate component having a functionality of about 2 prior to reacting the modified diisocyanate component with the polyol and second extender components.
  • a linear thermoplastic polyurethane elastomer composition is formed which has lower temperature processing characteristics compared to similar compositions wherein the diisocyanate compound is not modified.
  • the polyol component may be a polyether polyol
  • the first extender component is generally a polyol or amine compound having a molecular weight of less than about 500.
  • the first extender component comprises a diol.
  • the second extender component is included for optimum results.
  • the diisocyanate compound is modified so that the modified diisocyanate component has an NCO content of between about 14 and 33%, and preferably between about 20 and 26%.
  • the most advantageous diisocyanate compound is one that
  • compound having a molecular weight between about 60 and 250 such as 1,4-butane diol, tripropylene glycol, dipropylene glycol, propylene glycol, ethylene glycol, 1,6-hexane diol, 1,3-butane diol, neopentyl glycol, ethylene diamine or mixtures thereof.
  • the present invention also relates to a linear
  • thermoplastic polyurethane elastomer compositions comprising a mixture of a polycarbonate polyol and a polyether polyol; a diisocyanate compound; and first and second extenders.
  • the diisocyanate compound is initially reacted with one of the extenders in a molar ratio of above 2:1 so as to form a modified diisocyanate component having a functionality of about 2 prior to reaction with the other components.
  • This modified diisocyanate component provides relatively low temperature processing properties to the composition, whereas the polyol mixture provides superior hydrolytic stability and low temperature flexibility to the
  • the first extender component is a polyol or amine compound having a molecular weight of less than about 500, such as a diol, while the diisocyanate compound
  • the first extender component is a polyol or amine compound having a molecular weight between about 60 and 250, such as 1,4-butane diol, tripropylene glycol, dipropylene glycol, propylene glycol, ethylene glycol, 1,6- hexane diol, 1,3-butane diol, neopentyl glycol, ethylene diamine or mixtures thereof.
  • the polyether polyol and polycarbonate polyol are present in a relative amount of between 2 : 1 to 1:8.
  • the first extender is 1,4-butanediol and the second extender is tripropylene glycol
  • the modified diisocyanate component has an NCO content of between about 14 and 33%, preferably between about 20 and 26%.
  • the overall NCO/OH ratio of the entire composition is between about 0.95 and 1.05/1.
  • One preferred embodiment of this invention relates to a polyurethane elastomer based on a mixture of polycarbonate and polyether polyols, a modified diisocyanate component formed by reacting a diisocyanate compound with a low molecular weight extender such as tripropylene glycol, and a second extender of 1,4-butanediol.
  • a diisocyanate compound with a low molecular weight extender such as tripropylene glycol
  • polyester polyurethanes This polymer also has elastomeric characteristics and other physical properties which render it suitable for use in coated fabric
  • polycarbonate polyol can be used in any relative amounts provided that each are present in the composition. It has been found convenient to use a polyether polyol:
  • Any diisocyanate compound is suitable with those based on 4,4'-diphenyl methane diisocyanate being preferred.
  • diisocyanate can also be used, if desired, but these
  • liquid MDI will be used to designate an essentially difunctional modified MDI component prepared from the reaction of a low molecular weight polyol with an MDI compound to form a modified diisocyanate composition which is liquid at room
  • any polyol component can be used for reaction with the liquid MDI component, including polyether, polyester, polycaprolactone,
  • polycarbonate or polybutadiane polyols or mixtures thereof are preferred polyol component.
  • a preferred polyol component is mixture of a polyether polyol and polycarbonate polyol.
  • isocyanates mentioned above can instead be used, if desired.
  • an isophorone diisocyanate can be used to achieve better results than MDI.
  • toluene diisocyanate (TDI) can be used, but it is less reactive than MDI.
  • TDI toluene diisocyanate
  • amine extenders rather than polyol or diol extenders, should be used.
  • One skilled in the art can select the best combination of ingredients for any particular formulation.
  • a three to five gram sample of polymer was finely chopped and used to determine the temperature at which the polymer would flow at a measurable rate and to determine the rate itself on a Kayness, Inc. extrusion plastometer Model D-0051.
  • a measurable rate was defined as greater than 0.15 grams per 10 minutes. Thus at temperatures below the flow temperature, neither fusion of the polymer nor flow greater than 0.15 grams is achieved.
  • the flow rate is defined as the number of grams extruded from the barrel of the
  • Each formulation contains 1,4-butane diol as an extender in an amount necessary to achieve the final NCO/OH ratio.

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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)
  • Polyurethanes Or Polyureas (AREA)

Abstract

Des élastomères de polyuréthane linéaires d'un composant polyol, au moins deux diluants, et un composé de diisocyanate sont préparés en faisant réagir le composé de diisocyanate avec l'un des diluants pour former un composant de diisocyanate modifié ayant une fonctionnalité d'environ 2 avant de faire réagir ce composant modifié avec les autres composants de l'élastomère. Un composant de polyol préféré comprend un mélange d'un polyol de polycarbonate et un polyol de polyéther. Ces nouveaux élastomères possèdent une combinaison unique de caractéristiques telles que la stabilité hydrolitique, la résistance et la flexibilité, et peuvent être traités à des températures plus basses que les températures de traitement d'élastomères préparés à partir de compositions semblables dans lesquelles le composé isocyanate n'est pas modifié.
PCT/US1990/001477 1989-03-20 1990-03-19 Compositions elastomeres de polyurethane lineaire et utilisation de diisocyanates modifies pour preparer de telles compositions WO1990011309A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
KR1019910701135A KR920701290A (ko) 1989-03-20 1990-03-19 선형 폴리우레탄 탄성중합체 조성물과 이것을 제조하기 위한 변형 디이소시아네이트의 용도

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US326,865 1989-03-20
US326,183 1989-03-20
US07/326,183 US5013811A (en) 1989-03-20 1989-03-20 Use of modified diisocyanates for preparing linear thermoplastic polyurethane elastomers having improved properties
US07/326,865 US5001208A (en) 1989-03-20 1989-03-20 Linear polyurethane elastomer compositions based on mixed polycarbonate and polyether polyols

Publications (1)

Publication Number Publication Date
WO1990011309A1 true WO1990011309A1 (fr) 1990-10-04

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PCT/US1990/001477 WO1990011309A1 (fr) 1989-03-20 1990-03-19 Compositions elastomeres de polyurethane lineaire et utilisation de diisocyanates modifies pour preparer de telles compositions

Country Status (6)

Country Link
EP (1) EP0464141A4 (fr)
JP (1) JPH04504138A (fr)
KR (1) KR920701290A (fr)
AU (1) AU642409B2 (fr)
CA (1) CA2047678A1 (fr)
WO (1) WO1990011309A1 (fr)

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0571833A2 (fr) * 1992-05-26 1993-12-01 Bayer Ag Elastomères de polyuréthanes thermoplastiquement façonnables et leur procédé de préparation
EP0654625A1 (fr) * 1993-11-23 1995-05-24 W.L. GORE & ASSOCIATES GmbH Joint plat pour réservoirs d'essence
KR20140054123A (ko) * 2011-07-25 2014-05-08 노보머, 인코포레이티드 폴리우레탄에 이용하기 위한 지방족 폴리카보네이트
WO2015090916A1 (fr) * 2013-12-17 2015-06-25 Carl Freudenberg Kg Polyuréthane thermoplastique pour applications d'étanchéité
AU2014265117B2 (en) * 2010-09-16 2016-05-26 Baker Hughes Incorporated Polymer foam cell morphology control and use in borehole filtration devices
US10047188B2 (en) 2012-11-07 2018-08-14 Saudi Aramco Technologies Company High strength polyurethane foam compositions and methods
CN112424250A (zh) * 2018-07-12 2021-02-26 巴斯夫欧洲公司 玻璃纤维增强的tpu
CN114891181A (zh) * 2022-05-26 2022-08-12 浙江华峰合成树脂有限公司 一种聚氨酯树脂及其镜面合成革
CN117229471A (zh) * 2023-11-15 2023-12-15 长春设备工艺研究所 聚氨酯弹性体的改性方法及其3d打印温度参数优化方法

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU664158B2 (en) * 1990-09-12 1995-11-09 Polymedica Industries, Inc Biostable polyurethane products
JP6341405B2 (ja) * 2013-10-22 2018-06-13 Dic株式会社 ウレタン組成物及びウレタンエラストマー成形品

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3904796A (en) * 1972-05-04 1975-09-09 Bayer Ag Process for the production of polyurethane coatings
US4306052A (en) * 1980-09-25 1981-12-15 The Upjohn Company Thermoplastic polyester polyurethanes
US4307004A (en) * 1979-02-17 1981-12-22 Firma Carl Freudenberg Polyurethane urea heat seal adhesive for the preparation of heat sealable padding material
US4683171A (en) * 1985-02-05 1987-07-28 Asahi Glass Company, Ltd. Laminate and method for its preparation
US4705721A (en) * 1985-02-26 1987-11-10 Saint-Gobain Vitrage Polyurethane-based adhesive coating or film, and use of same in laminated glass panes
US4791187A (en) * 1986-08-19 1988-12-13 Bayer Akteingesellschaft Linear polyurethane elastomers, and a process for the preparation thereof
US4868268A (en) * 1986-07-05 1989-09-19 Bayer Aktiengesellschaft Process for preparing polyurethanes from an organic diisocyanate ester

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DD115142A1 (fr) * 1974-06-04 1975-09-12
JPS57205469A (en) * 1981-06-10 1982-12-16 Toyo Ink Mfg Co Ltd Solventless polyurethane adhesive for dry laminate
JPS62158712A (ja) * 1985-12-30 1987-07-14 Toyo Tire & Rubber Co Ltd 発泡ポリウレタンエラストマ−の製造法

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3904796A (en) * 1972-05-04 1975-09-09 Bayer Ag Process for the production of polyurethane coatings
US4307004A (en) * 1979-02-17 1981-12-22 Firma Carl Freudenberg Polyurethane urea heat seal adhesive for the preparation of heat sealable padding material
US4306052A (en) * 1980-09-25 1981-12-15 The Upjohn Company Thermoplastic polyester polyurethanes
US4683171A (en) * 1985-02-05 1987-07-28 Asahi Glass Company, Ltd. Laminate and method for its preparation
US4705721A (en) * 1985-02-26 1987-11-10 Saint-Gobain Vitrage Polyurethane-based adhesive coating or film, and use of same in laminated glass panes
US4868268A (en) * 1986-07-05 1989-09-19 Bayer Aktiengesellschaft Process for preparing polyurethanes from an organic diisocyanate ester
US4791187A (en) * 1986-08-19 1988-12-13 Bayer Akteingesellschaft Linear polyurethane elastomers, and a process for the preparation thereof

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See also references of EP0464141A4 *

Cited By (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0571833A3 (fr) * 1992-05-26 1994-03-23 Bayer Ag
EP0571833A2 (fr) * 1992-05-26 1993-12-01 Bayer Ag Elastomères de polyuréthanes thermoplastiquement façonnables et leur procédé de préparation
EP0654625A1 (fr) * 1993-11-23 1995-05-24 W.L. GORE & ASSOCIATES GmbH Joint plat pour réservoirs d'essence
AU2014265117B2 (en) * 2010-09-16 2016-05-26 Baker Hughes Incorporated Polymer foam cell morphology control and use in borehole filtration devices
US10351654B2 (en) 2011-07-25 2019-07-16 Saudi Aramco Technologies Company Polymer compositions and methods
KR20140054123A (ko) * 2011-07-25 2014-05-08 노보머, 인코포레이티드 폴리우레탄에 이용하기 위한 지방족 폴리카보네이트
US10982036B2 (en) 2011-07-25 2021-04-20 Saudi Aramco Technologies Company Polymer compositions and methods
US11021564B2 (en) 2012-11-07 2021-06-01 Saudi Aramco Technologies Company High strength polyurethane foam compositions and methods
US10428173B2 (en) 2012-11-07 2019-10-01 Saudi Aramco Technologies Company High strength polyurethane foam compositions and methods
US10047188B2 (en) 2012-11-07 2018-08-14 Saudi Aramco Technologies Company High strength polyurethane foam compositions and methods
US10227443B2 (en) 2013-12-17 2019-03-12 Carl Freudenberg Kg Thermoplastic polyurethane for seal applications
WO2015090916A1 (fr) * 2013-12-17 2015-06-25 Carl Freudenberg Kg Polyuréthane thermoplastique pour applications d'étanchéité
CN112424250A (zh) * 2018-07-12 2021-02-26 巴斯夫欧洲公司 玻璃纤维增强的tpu
CN114891181A (zh) * 2022-05-26 2022-08-12 浙江华峰合成树脂有限公司 一种聚氨酯树脂及其镜面合成革
CN114891181B (zh) * 2022-05-26 2024-03-12 浙江华峰合成树脂有限公司 一种聚氨酯树脂及其镜面合成革
CN117229471A (zh) * 2023-11-15 2023-12-15 长春设备工艺研究所 聚氨酯弹性体的改性方法及其3d打印温度参数优化方法

Also Published As

Publication number Publication date
EP0464141A4 (en) 1992-05-20
KR920701290A (ko) 1992-08-11
EP0464141A1 (fr) 1992-01-08
AU5355190A (en) 1990-10-22
AU642409B2 (en) 1993-10-21
CA2047678A1 (fr) 1990-09-21
JPH04504138A (ja) 1992-07-23

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