CN1215100C - 异氰酸酯的缩合催化剂,包括该催化剂的组合物,使用方法,和所得组合物 - Google Patents
异氰酸酯的缩合催化剂,包括该催化剂的组合物,使用方法,和所得组合物 Download PDFInfo
- Publication number
- CN1215100C CN1215100C CNB018215599A CN01821559A CN1215100C CN 1215100 C CN1215100 C CN 1215100C CN B018215599 A CNB018215599 A CN B018215599A CN 01821559 A CN01821559 A CN 01821559A CN 1215100 C CN1215100 C CN 1215100C
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- CN
- China
- Prior art keywords
- compound
- group
- isocyanate
- salt
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- 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.)
- Expired - Fee Related
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
- C07D251/40—Nitrogen atoms
- C07D251/42—One nitrogen atom
- C07D251/46—One nitrogen atom with oxygen or sulfur atoms attached to the two other ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D229/00—Heterocyclic compounds containing rings of less than five members having two nitrogen atoms as the only ring hetero atoms
-
- 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
-
- 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
- C08G18/09—Processes comprising oligomerisation of isocyanates or isothiocyanates involving reaction of a part of the isocyanate or isothiocyanate groups with each other in the reaction mixture
-
- 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
- C08G18/22—Catalysts containing metal compounds
- C08G18/24—Catalysts containing metal compounds of tin
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Polyurethanes Or Polyureas (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
产物/组分 | 实施例1 | 实施例2 | 实施例3 | 实施例4 | 实施例5 | 实施例6 | 实施例7 | 实施例8 | 实施例9 |
IPDI(%) | 39.3 | 91.5 | 53.0 | 45.4 | 49.1 | 67.8 | 73.7 | - | 28.0 |
HDI | 76.4 | ||||||||
催化剂(1) | K,HMDZ(0.1) | K,HMDZ(0.04) | K,HMDZ(0.04) | K,HMDZ(0.03) | K,HMDZ(0.03) | Li,HMDZ(0.5) | Li,HMDZ(0.4) | K,HMDZ(0.04) | Li8(Me)3SiO(5) |
温度 | 60℃ | 60℃ | 60℃ | 120℃ | 150℃ | 60℃ | 60℃ | 90℃ | 60℃ |
氩气喷射 | 无 | 无 | 有 | 有 | 有 | 无 | 无 | 有 | 无 |
三聚体+二聚体(%) | 33.1 | 5.6 | 27.7 | 33.9 | 33.8 | 20.1 | 16.4 | - | 37.9 |
双-三聚体(%) | 15.9 | 2.1 | 12.4 | 13.7 | 11.8 | 8.6 | 7.0 | - | 20.9 |
重质产物(三-三聚体)(%) | 11.7 | 0.8 | 6.9 | 7.0 | 5.2 | 3.5 | 2.9 | - | 13.2 |
产物/组分 | 相对于异氰酸酯重量的wt% |
IPDI(%) | 76.8% |
IPDI三甲基甲硅烷基脲 | 2.0% |
真二聚体(单脲丁啶二酮) | 痕量 |
未确认的脲或二脲 | |
三聚体(+氮尿嘧啶+缩二脲) | 15.9% |
重质产物 | 5.4% |
产物/组分 | 相对于异氰酸酯重量的wt% |
IPDI(%) | 74.5% |
IPDI三甲基甲硅烷基脲 | 4.7%* |
IUT** | 16.3% |
双-IUT | 4.3% |
催化剂 | 质量% | 溶剂 | 粗产物的外观 | 所发现的三聚体谱带,cm-1 |
Y(N(SiMe3)2)3 | 1% | 无 | 灰白色膏状物和不透明固体 | 16901464.5 |
Y(N(SiMe3)2)3 | 1% | 有 | 灰白色膏状物 | 16861466.5 |
金属中心 | RM的外观 | 三聚体谱带,cm-1 | 所存在的实体(GPC/FTIR分析) | ||||
Y | 灰白色膏状物 | 16861466.5 | 重质产物 | 三-三聚体 | 双-三聚体 | 三聚体 | HDI |
Nd | 灰白色膏状物 | 1689.51463.5 | 重质产物 | 三-三聚体 | 双-三聚体 | 三聚体 | HDI |
Sm | 黄色膏状物 | 16891463.5 | 重质产物 | 三-三聚体 | 双-三聚体 | 三聚体 | HDI |
催化剂质量% | RM的外观 | 三聚体谱带,cm-1 | 所存在的实体和它们的量(GPC/FTIR分析) | DC | ||||
1% | 灰白色膏状物 | 16861466.5 | 重质产物 | 三-三聚体 | 双-三聚体 | 三聚体 | HDI | |
0.2% | 黄色粘性液体 | 1686.51465 | 重质产物1.2% | 三-三聚体0.9% | 双-三聚体2.9% | 三聚体+缩二脲12.3% | HDI40.5% | Ov:31%T+B:21% |
0.1% | 黄色粘性液体 | 16861460 | 双-三聚体0.7% | 三聚体+缩二脲6.3% | HDI83.3% | Ov:8%T+B:7% |
T,℃ | RM的外观 | 三聚体谱带,cm-1 | 所存在的实体和它们的量(GPC/FTIR分析) | DC | ||||
60 | 黄色粘性液体 | 1686.51465 | 双-三聚体0.7% | 三聚体+缩二脲6.3% | HDI83.3% | Ov:8%T+B:7% | ||
100 | 黄色粘性液体 | 16891464.5 | 重质产物0.8% | 三-三聚体0.4% | 双-三聚体2.1% | 三聚体13% | HDI64.3% | Ov:25%T:20% |
催化剂 | 质量% | 粗产物的外观 | 所发现的三聚体谱带,cm-1 |
Sm(Siam)3PhCN | 1% | 不透明膏状物 | 1688.51464 |
NaSiam | 1% | 不透明固体 | 16861465.5 |
LiSiam | 1% | 不透明固体 | 16891465 |
金属中心 | RM的外观 | 三聚体谱带,cm | 所存在的实体(GPC/FTIR分析) | ||||
Sm | 不透明膏状物 | 1688.51464 | 重质产物 | 三-三聚体 | 双-三聚体 | 三聚体 | HDI |
Yb | 不透明膏状物 | 1688.51463 | 重质产物 | 三-三聚体 | 双-三聚体 | 三聚体 | HDI |
Y | 灰白色膏状物 | 1688.51463 | 重质产物 | 三-三聚体 | 双-三聚体 | 三聚体 | HDI |
催化剂质量% | RM的外观 | 三聚体谱带,cm-1 | 所存在的实体和它们的量(GPC/FTIR分析) | DC | ||||
1% | 灰白色膏状物 | 1688.51463 | 重质产物 | 三-三聚体 | 双-三聚体 | 三聚体 | HDI | |
0.2% | 黄色粘性液体 | 16861460 | 重质产物2.7% | 三-三聚体1.7% | 双-三聚体4.3% | 三聚体+缩二脲13.4% | HDI41.3% | Ov:35%T+B:21% |
催化剂 | RM的外观 | 三聚体谱带,cm-1 | 所存在的实体和它们的量(GPC/FTIR分析) | ||||
Y(N(SiMe3)2)3(1质量%) | 淡黄色液体 | 不非常明显 | 重质产物 | 缩二脲-三聚体 | 脲 | 氨基甲酸酯 | IPDI |
NaN(SiMe3)2(1质量%) | 淡黄色膏状物 | 16921446.5 | 重质产物 | 三-三聚体 | 双-三聚体 | 三聚体 | IPDI |
金属中心 | RM的外观 | 三聚体谱带,cm-1 | 所存在的实体和它们的量(GPC/FTIR分析) | DC | |||
Y | 淡黄色不太粘的液体 | 弱 | 三聚体+缩二脲 | 脲 | 氨基甲酸酯 | IPDI | |
Sm | 淡黄色不太粘的液体 | 弱 | 三聚体+缩二脲1.5% | 脲4.3% | 二聚体0.4% | IPDI76% | Ov:0.1% |
T,℃ | RM的外观 | 三聚体谱带,cm-1 | 所存在的实体和它们的量(GPC/FTIR分析) | DC | |||
60 | 黄色不太粘的液体 | 弱 | 缩二脲+三聚体 | 脲 | 氨基甲酸酯 | IPDI | |
100 | 黄色不太粘的液体 | 有 | 缩二脲+三聚体2.2% | 脲5% | 氨基甲酸酯 | IPDI53% | Ov:14%T+B:4% |
催化剂 | 质量% | 粗产物的外观 | 所发现的三聚体谱带,cm-1 |
Sm(Siam)3PhCN | 1% | 黄色不太粘的液体 | 不显著 |
NaSiam | 1% | 黄色膏状物 | 16901445 |
质量% | RM的外观 | 所存在的实体(GPC/FTIR分析) | |||
1% | 黄色不太粘的液体 | 缩二脲 | 脲 | 氨基甲酸酯 | IPDI |
5% | 淡黄色不太粘的液体 | 缩二脲+三聚体 | 脲 | 氨基甲酸酯 | IPDI |
Claims (41)
Applications Claiming Priority (8)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR00/17323 | 2000-12-29 | ||
FR00/17317 | 2000-12-29 | ||
FR00/17315 | 2000-12-29 | ||
FR0017323A FR2818976B1 (fr) | 2000-12-29 | 2000-12-29 | Procede de (cyclo) condensation au moyen d'un sel de silazane d'erbium |
FR0017315A FR2818973B1 (fr) | 2000-12-29 | 2000-12-29 | Nouveau procede de (cyclo) condensation d'isocyanates au moyen d'un sel de silazane d'etain |
FR0017317A FR2818975B1 (fr) | 2000-12-29 | 2000-12-29 | Nouveau procede de (cyclo) condensation, notamment de (cyclo) trimerisation catalytique d'isocyanates |
FR0116723A FR2833864A1 (fr) | 2001-12-21 | 2001-12-21 | Catalyseur de condensation pour isocyanate, composition en contenant, procede d'utilisation, et compositions obtenues |
FR01/16723 | 2001-12-21 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN1484660A CN1484660A (zh) | 2004-03-24 |
CN1215100C true CN1215100C (zh) | 2005-08-17 |
Family
ID=27445927
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CNB018215599A Expired - Fee Related CN1215100C (zh) | 2000-12-29 | 2001-12-28 | 异氰酸酯的缩合催化剂,包括该催化剂的组合物,使用方法,和所得组合物 |
Country Status (8)
Country | Link |
---|---|
US (1) | US6946538B2 (zh) |
EP (1) | EP1358238B1 (zh) |
CN (1) | CN1215100C (zh) |
AT (1) | ATE463522T1 (zh) |
BR (1) | BR0116559A (zh) |
CA (1) | CA2432960A1 (zh) |
DE (1) | DE60141771D1 (zh) |
WO (1) | WO2002053614A1 (zh) |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2818974B1 (fr) * | 2000-12-29 | 2003-10-24 | Rhodia Chimie Sa | (cyclo) condensation de composes isocyanates |
JP7029295B2 (ja) * | 2015-04-21 | 2022-03-03 | コベストロ、ドイチュラント、アクチエンゲゼルシャフト | 高い熱安定性を有するポリイソシアヌレートプラスチック |
EP3085718B1 (de) * | 2015-04-21 | 2024-04-17 | Covestro Deutschland AG | Polyisocyanuratkunststoff enthaltend siloxangruppen und verfahren zu dessen herstellung |
EP3715396A1 (de) * | 2019-03-26 | 2020-09-30 | PolyU GmbH | Zusammensetzung und verfahren zur herstellung silylierter polymere und deren verwendung |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4003859A (en) | 1974-01-30 | 1977-01-18 | The Upjohn Company | Novel process for trimerizing polyisocyanates |
FR2572402B1 (fr) | 1984-10-30 | 1988-03-11 | Rhone Poulenc Spec Chim | Procede de preparation de polyisocyanates polyisocyanurates par cyclotrimerisation catalytique de polyisocyanates |
GB2203159B (en) * | 1987-04-03 | 1990-12-12 | Asahi Chemical Ind | An isocyanurate polyisocyanate and its use as a curing agent for a two-component polyurethane composition |
US5017695A (en) * | 1987-12-03 | 1991-05-21 | Rhone-Poulenc, Inc. | Ceric hydrocarbyl silyloxides and process for their preparation |
-
2001
- 2001-12-28 AT AT01989673T patent/ATE463522T1/de not_active IP Right Cessation
- 2001-12-28 BR BR0116559-3A patent/BR0116559A/pt active Pending
- 2001-12-28 US US10/450,261 patent/US6946538B2/en not_active Expired - Lifetime
- 2001-12-28 WO PCT/FR2001/004228 patent/WO2002053614A1/fr not_active Application Discontinuation
- 2001-12-28 DE DE60141771T patent/DE60141771D1/de not_active Expired - Lifetime
- 2001-12-28 EP EP01989673A patent/EP1358238B1/fr not_active Expired - Lifetime
- 2001-12-28 CN CNB018215599A patent/CN1215100C/zh not_active Expired - Fee Related
- 2001-12-28 CA CA002432960A patent/CA2432960A1/fr not_active Abandoned
Also Published As
Publication number | Publication date |
---|---|
ATE463522T1 (de) | 2010-04-15 |
CA2432960A1 (fr) | 2002-07-11 |
WO2002053614A1 (fr) | 2002-07-11 |
US6946538B2 (en) | 2005-09-20 |
US20040024212A1 (en) | 2004-02-05 |
EP1358238A1 (fr) | 2003-11-05 |
EP1358238B1 (fr) | 2010-04-07 |
DE60141771D1 (de) | 2010-05-20 |
BR0116559A (pt) | 2004-02-17 |
CN1484660A (zh) | 2004-03-24 |
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