CN1280588A - 异氰酸酯的三聚催化剂和方法 - Google Patents
异氰酸酯的三聚催化剂和方法 Download PDFInfo
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- CN1280588A CN1280588A CN98811699A CN98811699A CN1280588A CN 1280588 A CN1280588 A CN 1280588A CN 98811699 A CN98811699 A CN 98811699A CN 98811699 A CN98811699 A CN 98811699A CN 1280588 A CN1280588 A CN 1280588A
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- carbon atom
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- 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
- C08G18/38—Low-molecular-weight compounds having heteroatoms other than oxygen
- C08G18/3819—Low-molecular-weight compounds having heteroatoms other than oxygen having nitrogen
- C08G18/3842—Low-molecular-weight compounds having heteroatoms other than oxygen having nitrogen containing heterocyclic rings having at least one nitrogen atom in the ring
- C08G18/3848—Low-molecular-weight compounds having heteroatoms other than oxygen having nitrogen containing heterocyclic rings having at least one nitrogen atom in the ring containing two nitrogen atoms in the ring
-
- 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
- C08G18/02—Polymeric products of isocyanates or isothiocyanates of isocyanates or isothiocyanates only
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/0234—Nitrogen-, phosphorus-, arsenic- or antimony-containing compounds
- B01J31/0235—Nitrogen containing compounds
- B01J31/0239—Quaternary ammonium compounds
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/0234—Nitrogen-, phosphorus-, arsenic- or antimony-containing compounds
- B01J31/0235—Nitrogen containing compounds
- B01J31/0244—Nitrogen containing compounds with nitrogen contained as ring member in aromatic compounds or moieties, e.g. pyridine
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/0234—Nitrogen-, phosphorus-, arsenic- or antimony-containing compounds
- B01J31/0255—Phosphorus containing compounds
- B01J31/0267—Phosphines or phosphonium compounds, i.e. phosphorus bonded to at least one carbon atom, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, the other atoms bonded to phosphorus being either carbon or hydrogen
- B01J31/0268—Phosphonium compounds, i.e. phosphine with an additional hydrogen or carbon atom bonded to phosphorous so as to result in a formal positive charge on phosphorous
-
- 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
- C08G18/02—Polymeric products of isocyanates or isothiocyanates of isocyanates or isothiocyanates only
- C08G18/022—Polymeric products of isocyanates or isothiocyanates of isocyanates or isothiocyanates only the polymeric products containing isocyanurate groups
-
- 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
- C08G18/16—Catalysts
- C08G18/18—Catalysts containing secondary or tertiary amines or salts thereof
- C08G18/1875—Catalysts containing secondary or tertiary amines or salts thereof containing ammonium salts or mixtures of secondary of tertiary amines and acids
-
- 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
- C08G18/16—Catalysts
- C08G18/18—Catalysts containing secondary or tertiary amines or salts thereof
- C08G18/20—Heterocyclic amines; Salts thereof
- C08G18/2009—Heterocyclic amines; Salts thereof containing one heterocyclic ring
- C08G18/2027—Heterocyclic amines; Salts thereof containing one heterocyclic ring having two nitrogen atoms in the ring
-
- 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
- C08L75/04—Polyurethanes
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/30—Addition reactions at carbon centres, i.e. to either C-C or C-X multiple bonds
- B01J2231/34—Other additions, e.g. Monsanto-type carbonylations, addition to 1,2-C=X or 1,2-C-X triplebonds, additions to 1,4-C=C-C=X or 1,4-C=-C-X triple bonds with X, e.g. O, S, NH/N
- B01J2231/341—1,2-additions, e.g. aldol or Knoevenagel condensations
-
- 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
- C08G2115/00—Oligomerisation
- C08G2115/02—Oligomerisation to isocyanurate groups
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- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Polyurethanes Or Polyureas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Abstract
Description
实施例 | 催化剂 | [cata*]wt% | 反应温度(℃) | DC IPDI(%) |
1 | 胆碱碳酸氢盐 | 0.07 | 85 | 10 |
2 | 胆碱碳酸氢盐 | 0.2 | 60 | 40 |
3 | 胆碱氢氧化物 | 0.07 | 85 | 40 |
4 | 胆碱亚硫酸氢盐 | 0.07 | 85 | 0 |
5 | 胆碱酒石酸氢盐 | 0.2 | 80 | 0 |
实施例 | 催化剂 | 助催化剂 | [cata]wt% | [cocata]mmol/100g | 反应温度℃ | DC%IPDI | APHA色度 |
6 | 胆碱碳酸氢盐 | 咪唑 | 0.05 | 4 | 80 | 70 | 70 |
7 | 胆碱碳酸氢盐 | 咪唑 | 0.028 | 4 | 80 | 60 | 60 |
8 | 胆碱碳酸氢盐 | 无 | 0.2 | 0 | 80 | 50 | 140 |
9 | 胆碱碳酸氢盐 | 无 | 0.15 | 0 | 80 | 32 | 140 |
Claims (25)
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR97/13856 | 1997-11-04 | ||
FR97/13855 | 1997-11-04 | ||
FR9713855A FR2770532B1 (fr) | 1997-11-04 | 1997-11-04 | Catalyseur de trimerisation d'isocyanates, a base d'un hydrogenocarbonate |
FR9713856A FR2770533B1 (fr) | 1997-11-04 | 1997-11-04 | Utilisation d'imidazole en tant que co-catalyseur de la trimerisation d'isocyanates |
Publications (2)
Publication Number | Publication Date |
---|---|
CN1280588A true CN1280588A (zh) | 2001-01-17 |
CN1184248C CN1184248C (zh) | 2005-01-12 |
Family
ID=26233919
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CNB988116995A Expired - Fee Related CN1184248C (zh) | 1997-11-04 | 1998-11-04 | 异氰酸酯的三聚催化剂和方法 |
Country Status (12)
Country | Link |
---|---|
US (2) | US6635761B1 (zh) |
EP (2) | EP1375545B1 (zh) |
JP (1) | JP4342723B2 (zh) |
KR (1) | KR100549652B1 (zh) |
CN (1) | CN1184248C (zh) |
AT (1) | ATE251648T1 (zh) |
AU (1) | AU1159699A (zh) |
BR (1) | BR9813932A (zh) |
CA (1) | CA2307747A1 (zh) |
DE (1) | DE69818857T2 (zh) |
WO (1) | WO1999023128A1 (zh) |
ZA (1) | ZA9810038B (zh) |
Cited By (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1302038C (zh) * | 2001-05-14 | 2007-02-28 | 拜尔公司 | 制备具有脲二酮、异氰脲酸酯和亚氨代噁二嗪二酮结构的脂族多异氰酸酯的方法 |
CN105032490A (zh) * | 2015-07-17 | 2015-11-11 | 华南理工大学 | 一种复配催化剂及在制备混合二异氰酸酯三聚体中的应用 |
CN105829375A (zh) * | 2013-12-19 | 2016-08-03 | 东曹株式会社 | 脲基甲酸酯-异氰脲酸酯化催化剂、多异氰酸酯组合物和该组合物的制造方法以及双组分型涂料组合物 |
CN106902872A (zh) * | 2017-03-29 | 2017-06-30 | 万华化学集团股份有限公司 | 一种异氰酸酯聚合催化剂及其制备方法,及其用于制备聚异氰酸酯的方法 |
CN107021920A (zh) * | 2016-08-12 | 2017-08-08 | 万华化学集团股份有限公司 | 一种异氰酸酯聚合催化剂及其制备方法,及其用于制备聚异氰酸酯的方法 |
CN107531875A (zh) * | 2015-04-21 | 2018-01-02 | 科思创德国股份有限公司 | 用于生产具有功能化表面的聚异氰脲酸酯塑料的方法 |
CN107868226A (zh) * | 2017-12-07 | 2018-04-03 | 万华化学集团股份有限公司 | 一种窄分布二异氰酸酯三聚体的制备方法 |
CN108822276A (zh) * | 2018-05-29 | 2018-11-16 | 武汉理工大学 | 一种pvc/pet复合膜胶黏剂的制备方法 |
CN110760055A (zh) * | 2019-10-29 | 2020-02-07 | 万华化学(宁波)有限公司 | 一种多异氰酸酯组合物及制备方法 |
CN111465632A (zh) * | 2017-12-21 | 2020-07-28 | 科思创德国股份有限公司 | 制备含异氰脲酸酯基团的异氰酸酯混合物的方法 |
CN112250835A (zh) * | 2020-09-14 | 2021-01-22 | 万华化学(宁波)有限公司 | 一种制备无色多异氰酸酯组合物的方法 |
Families Citing this family (39)
Publication number | Priority date | Publication date | Assignee | Title |
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ZA9810038B (en) * | 1997-11-04 | 2000-05-03 | Rhodia Chimie Sa | A catalyst and a method for the trimerization of isocyanates. |
FR2804112B1 (fr) * | 2000-01-20 | 2004-04-30 | Rhodia Chimie Sa | Procede d'obtention de cyclotrimeres d'isocyanate(s) ramifie(s) faiblement colore(s) et composition en decoulant |
CN100341860C (zh) | 2000-01-20 | 2007-10-10 | 罗狄亚化学公司 | 制备轻度着色的支化多异氰酸酯的方法及所得到的组合物 |
FR2808528B1 (fr) * | 2000-05-04 | 2004-05-21 | Rhodia Chimie Sa | Procede d'obtention de polyisocyanate(s) ramifie(s) faiblement colore(s), et composition en decoulant |
FR2818974B1 (fr) * | 2000-12-29 | 2003-10-24 | Rhodia Chimie Sa | (cyclo) condensation de composes isocyanates |
DE10123416A1 (de) * | 2001-05-14 | 2002-11-21 | Bayer Ag | Verfahren zur Herstellung von Polyisocyanaten |
DE10131525A1 (de) * | 2001-07-02 | 2003-01-16 | Degussa | Verfahren zur Herstellung von geruchsarmen und lagerstabilen monomerhaltigen Polyisocyanuraten aus Isophorondiisocyanat |
WO2005009601A2 (en) * | 2003-07-24 | 2005-02-03 | Huntsman Petrochemical Corporation | Low-odor catalyst for isocyanate-derived foams and elastomers |
FR2929612B1 (fr) * | 2008-04-03 | 2011-02-04 | Rhodia Operations | Procede d'oligomerisation des isocyanates en continu |
CN102272181A (zh) * | 2008-11-10 | 2011-12-07 | 陶氏环球技术有限责任公司 | 异氰酸酯三聚催化剂体系,前体制剂,使异氰酸酯三聚的方法,由其制备的硬质聚异氰脲酸酯/聚氨酯泡沫体,和制备这种泡沫体的方法 |
WO2013079614A2 (de) * | 2011-11-30 | 2013-06-06 | Bayer Intellectual Property Gmbh | Verfahren zur kontinuierlichen isocyanatmodifizierung |
EP2847246B1 (en) * | 2012-05-08 | 2016-04-20 | Basf Se | Preparation of polyisocyanates having isocyanurate groups and their use |
CN107531876B (zh) | 2015-04-21 | 2021-02-09 | 科思创德国股份有限公司 | 具有高热稳定性的聚异氰脲酸酯塑料 |
CA2980669C (en) | 2015-04-21 | 2023-09-19 | Covestro Deutschland Ag | Polyisocyanurate polymers and process for the production of polyisocyanurate polymers |
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EP3286240A1 (en) | 2015-04-21 | 2018-02-28 | Covestro Deutschland AG | Solids based on polyisocvanurate polymers produced under adiabatic conditions |
EP3085719A1 (de) | 2015-04-21 | 2016-10-26 | Covestro Deutschland AG | Hydrophob modifizierter polyisocyanuratkunststoff und verfahren zu dessen herstellung |
US9815739B2 (en) | 2015-10-30 | 2017-11-14 | Covestro Llc | Polyisocyanurate based cement for wellbore fluid loss prevention |
ES2823248T3 (es) | 2016-10-18 | 2021-05-06 | Covestro Intellectual Property Gmbh & Co Kg | Revestimientos duros con alta estabilidad química y mecánica |
US20210388153A1 (en) | 2016-10-18 | 2021-12-16 | Covestro Deutschland Ag | Coating of wires with catalytically crosslinked blocked polyisocyanates |
JP2019536849A (ja) | 2016-10-18 | 2019-12-19 | コベストロ、ドイチュラント、アクチエンゲゼルシャフトCovestro Deutschland Ag | ブロックトポリイソシアネートの触媒架橋によるプラスチックの製造 |
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EP3381962A1 (de) | 2017-03-29 | 2018-10-03 | Covestro Deutschland AG | Erzeugung von polyisocyanuratschichten durch getrennte auftragung von isocyanatkomponenten und katalysatoren |
EP3421516A1 (de) | 2017-06-28 | 2019-01-02 | Covestro Deutschland AG | Gefärbte kunststoffe basierend auf vernetzten polyisocyanaten |
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WO2020016119A1 (de) | 2018-07-16 | 2020-01-23 | Covestro Deutschland Ag | Verfahren zur oligomerisierung von isocyanaten mit polyedrischen silsesquioxan-katalysatoren |
WO2020079160A1 (de) | 2018-10-19 | 2020-04-23 | Covestro Deutschland Ag | Wasserfrei härtende klebstoffe auf polyisocyanatbasis |
CN113286836B (zh) | 2019-01-22 | 2024-02-13 | 科思创知识产权两合公司 | 基于双重固化的氨基甲酸酯和异氰脲酸酯聚合物的复合材料 |
WO2020174009A1 (de) | 2019-02-27 | 2020-09-03 | Covestro Intellectual Property Gmbh & Co. Kg | Polyisocyanuratwerkstoffe als elektrovergussmassen |
EP3763792A1 (de) | 2019-07-11 | 2021-01-13 | Covestro Deutschland AG | Verfahren zur herstellung von isocyanuraten aus uretdionen |
US20230211530A1 (en) | 2020-07-02 | 2023-07-06 | Covestro Deutschland Ag | Coatings from polyisocyanurate coatings (rim) and their use in injection molding processes |
EP4314102A1 (en) | 2021-03-29 | 2024-02-07 | Covestro Deutschland AG | Polyisocyanurate-prepregs and fiber composite components produced therefrom |
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Family Cites Families (11)
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US3980594A (en) * | 1975-04-23 | 1976-09-14 | The General Tire & Rubber Company | Trimerization of aromatic isocyanates catalyzed by certain ammonium salts |
US4040992A (en) * | 1975-07-29 | 1977-08-09 | Air Products And Chemicals, Inc. | Catalysis of organic isocyanate reactions |
DE2806731A1 (de) * | 1978-02-17 | 1979-08-23 | Bayer Ag | Verfahren zur herstellung von isocyanuratgruppen aufweisenden polyisocyanaten |
JPS57111310A (en) * | 1980-12-26 | 1982-07-10 | Achilles Corp | Production of rigid foam |
US4542214A (en) * | 1982-03-04 | 1985-09-17 | Air Products And Chemicals, Inc. | Carbamate and carbonate salts of tertiary amines |
JP2770329B2 (ja) * | 1988-07-22 | 1998-07-02 | 大日本インキ化学工業株式会社 | ポリイソシアネートの製造方法 |
DE4005762A1 (de) * | 1990-02-23 | 1991-08-29 | Bayer Ag | Trimerisierungskatalysatoren, ein verfahren zu ihrer herstellung und ihre verwendung bei der herstellung von isocyanuratgruppen aufweisenden polyisocyanaten |
JP3044261B2 (ja) | 1990-04-11 | 2000-05-22 | 東ソー株式会社 | 通気性に優れた軟質ポリウレタンフォ−ムの製造法 |
CA2052908A1 (en) * | 1990-11-06 | 1992-05-07 | Charles M. Milliren | System for the production of toluene diisocyanate based flexible foams and the flexible foams produced therefrom |
DE4405055A1 (de) * | 1994-02-17 | 1995-08-24 | Basf Ag | Verfahren zur Herstellung von Isocyanuratgruppen aufweisenden Polyisocyanaten und ihre Verwendung |
ZA9810038B (en) * | 1997-11-04 | 2000-05-03 | Rhodia Chimie Sa | A catalyst and a method for the trimerization of isocyanates. |
-
1998
- 1998-11-03 ZA ZA9810038A patent/ZA9810038B/xx unknown
- 1998-11-04 EP EP03020852.4A patent/EP1375545B1/fr not_active Expired - Lifetime
- 1998-11-04 AU AU11596/99A patent/AU1159699A/en not_active Abandoned
- 1998-11-04 KR KR1020007004756A patent/KR100549652B1/ko not_active IP Right Cessation
- 1998-11-04 DE DE69818857T patent/DE69818857T2/de not_active Expired - Lifetime
- 1998-11-04 US US09/530,607 patent/US6635761B1/en not_active Expired - Lifetime
- 1998-11-04 EP EP98954515A patent/EP1027380B1/fr not_active Expired - Lifetime
- 1998-11-04 AT AT98954515T patent/ATE251648T1/de not_active IP Right Cessation
- 1998-11-04 CA CA002307747A patent/CA2307747A1/fr not_active Abandoned
- 1998-11-04 BR BR9813932-0A patent/BR9813932A/pt not_active IP Right Cessation
- 1998-11-04 WO PCT/FR1998/002359 patent/WO1999023128A1/fr active IP Right Grant
- 1998-11-04 CN CNB988116995A patent/CN1184248C/zh not_active Expired - Fee Related
- 1998-11-04 JP JP2000518997A patent/JP4342723B2/ja not_active Expired - Fee Related
-
2003
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CN1302038C (zh) * | 2001-05-14 | 2007-02-28 | 拜尔公司 | 制备具有脲二酮、异氰脲酸酯和亚氨代噁二嗪二酮结构的脂族多异氰酸酯的方法 |
CN105829375A (zh) * | 2013-12-19 | 2016-08-03 | 东曹株式会社 | 脲基甲酸酯-异氰脲酸酯化催化剂、多异氰酸酯组合物和该组合物的制造方法以及双组分型涂料组合物 |
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Also Published As
Publication number | Publication date |
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WO1999023128A1 (fr) | 1999-05-14 |
US6635761B1 (en) | 2003-10-21 |
CN1184248C (zh) | 2005-01-12 |
DE69818857D1 (de) | 2003-11-13 |
CA2307747A1 (fr) | 1999-05-14 |
DE69818857T2 (de) | 2004-08-19 |
ATE251648T1 (de) | 2003-10-15 |
AU1159699A (en) | 1999-05-24 |
ZA9810038B (en) | 2000-05-03 |
US7091341B2 (en) | 2006-08-15 |
JP2001521952A (ja) | 2001-11-13 |
EP1375545A1 (fr) | 2004-01-02 |
BR9813932A (pt) | 2000-09-19 |
KR100549652B1 (ko) | 2006-02-08 |
EP1375545B1 (fr) | 2016-06-29 |
KR20010031693A (ko) | 2001-04-16 |
EP1027380B1 (fr) | 2003-10-08 |
US20050080259A1 (en) | 2005-04-14 |
JP4342723B2 (ja) | 2009-10-14 |
EP1027380A1 (fr) | 2000-08-16 |
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