JP5366829B2 - cisおよび/またはtrans−オルト−シクロヘキサンジアミン開始ポリオールとそれから作製された硬質ポリウレタンフォーム - Google Patents
cisおよび/またはtrans−オルト−シクロヘキサンジアミン開始ポリオールとそれから作製された硬質ポリウレタンフォーム Download PDFInfo
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- JP5366829B2 JP5366829B2 JP2009548405A JP2009548405A JP5366829B2 JP 5366829 B2 JP5366829 B2 JP 5366829B2 JP 2009548405 A JP2009548405 A JP 2009548405A JP 2009548405 A JP2009548405 A JP 2009548405A JP 5366829 B2 JP5366829 B2 JP 5366829B2
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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
- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
- C08G18/50—Polyethers having heteroatoms other than oxygen
-
- 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
- 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
-
- 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
- C08G18/50—Polyethers having heteroatoms other than oxygen
- C08G18/5021—Polyethers having heteroatoms other than oxygen having nitrogen
- C08G18/5024—Polyethers having heteroatoms other than oxygen having nitrogen containing primary and/or secondary amino groups
- C08G18/5027—Polyethers having heteroatoms other than oxygen having nitrogen containing primary and/or secondary amino groups directly linked to carbocyclic 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
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/26—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
-
- 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
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/26—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
- C08G65/2618—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing nitrogen
- C08G65/2621—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing nitrogen containing amine groups
- C08G65/2624—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing nitrogen containing amine groups containing aliphatic amine groups
-
- 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
- C08J9/22—After-treatment of expandable particles; Forming foamed products
-
- 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
Landscapes
- 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Description
a)少なくとも
1)75から560のヒドロキシル当量を有する本発明の第1の態様によるアミン開始ポリオール、またはそのポリオールと少なくとも1種類のその他のポリオールとの混合物であって、但しそのような混合物は、第1の態様のアミン開始ポリオールを少なくとも5重量%含有している混合物と、
2)少なくとも1種類の炭化水素、ハイドロフルオロカーボン、ハイドロクロロフルオロカーボン、フルオロカーボン、ジアルキルエーテル、またはフッ素置換ジアルキルエーテル物理発泡剤と、
3)少なくとも1種類のポリイソシアネートと
を含有する反応混合物を形成するステップと、
b)前記反応混合物が膨張し、硬化して硬質ポリウレタンフォームを形成するような条件下に、前記反応混合物を置くステップと
を含む、硬質ポリウレタンフォームを調製するための方法でもある。
(式中、各Rは独立に、水素またはC1〜C4アルキルである)。各Rは、好ましくは水素またはメチルである。各Rは、最も好ましくは水素であり、この場合、開始剤化合物は1,2−ジアミノシクロヘキサンになる。前述の構造に対応する2種または開始剤化合物の混合物を、使用することができる。
Rは、上記構造Iに関する場合と同じ意味を、構造IIおよびIIIで有する。オルト−シクロヘキサンジアミン化合物は、本質的に全てcis−異性体でよく、即ちオルト−シクロヘキサンジアミンの90%以上、好ましくは95%以上が、cis−異性体の形で存在する。あるいは、オルト−シクロヘキサンジアミン化合物は、本質的に全てtrans−異性体でよく、即ちオルト−シクロヘキサンジアミンの90%以上、好ましくは95%以上、さらにより好ましくは98%以上が、trans−異性体の形で存在する。本質的に全てtrans−異性体を含有する混合物から調製されたポリオールは、cis−およびtrans−オルト−シクロヘキサンジアミンの混合物を使用して作製されたその他の点では同様のポリオールよりも、著しく高い粘度を有する傾向があることが分かった。コストの観点から、そして低粘度生成物が所望される場合には、cis−およびtrans−オルト−シクロヘキサンジアミンの混合物を使用する方が都合が良い場合もある。混合物は、オルト−シクロヘキサンジアミンの全重量に対して10から90%のcis−異性体、好ましくは20から80%、特に20から50%のcis−異性体を含有することができる。
Claims (5)
- a)少なくとも、
1)少なくとも1種類のC2〜C4アルキレンオキシドと、少なくとも1種類のオルトシクロヘキサンジアミン開始剤化合物との反応生成物であり、3.3から4.0の平均官能価、および75から560のヒドロキシル当量を有する、アミン開始ポリオール、または該アミン開始ポリオールと少なくとも1種類のその他のポリオールとの混合物であって、前記アミン開始ポリオールを少なくとも5重量%含有することを条件とする混合物、
2)少なくとも1種類の発泡剤、および
3)少なくとも1種類のポリイソシアネート
を含有する反応混合物を形成するステップと、
b)前記反応混合物を、前記反応混合物が膨張し、硬化して硬質ポリウレタンフォームを形成するような条件下に置くステップと
を含む、硬質ポリウレタンフォームを調製するための方法。 - 前記反応混合物が前記発泡剤以外の成分として水を含む、請求項1に記載の方法。
- オルトシクロヘキサンジアミン化合物が、下記の構造によって表される、請求項1または2に記載の方法。
(式中、各Rは独立に、水素またはC1〜C4アルキルである) - 前記オルトシクロヘキサンジアミン化合物が、前記オルトシクロヘキサンジアミン化合物の重量に対して90から100%のtrans−オルトシクロヘキサンジアミン異性体および0から10%のcis−オルトシクロヘキサンジアミン異性体を含有する、請求項3に記載の方法。
- 前記オルトシクロヘキサンジアミン化合物が、前記シクロヘキサンジアミン化合物の総重量に対して98から100%のtrans−1,2−シクロヘキサジアミンおよび0から2%のcis−1,2−シクロヘキサンジアミンを含有する、請求項4に記載の方法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US89833407P | 2007-01-30 | 2007-01-30 | |
US60/898,334 | 2007-01-30 | ||
PCT/US2008/052396 WO2008094963A1 (en) | 2007-01-30 | 2008-01-30 | Cis and/or trans-ortho-cyclohexanediamine-initiated polyols and rigid polyurethane foam made therefrom |
Publications (3)
Publication Number | Publication Date |
---|---|
JP2010516818A JP2010516818A (ja) | 2010-05-20 |
JP2010516818A5 JP2010516818A5 (ja) | 2011-03-17 |
JP5366829B2 true JP5366829B2 (ja) | 2013-12-11 |
Family
ID=39415228
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2009548405A Active JP5366829B2 (ja) | 2007-01-30 | 2008-01-30 | cisおよび/またはtrans−オルト−シクロヘキサンジアミン開始ポリオールとそれから作製された硬質ポリウレタンフォーム |
Country Status (10)
Country | Link |
---|---|
US (1) | US8318826B2 (ja) |
EP (1) | EP2115027B1 (ja) |
JP (1) | JP5366829B2 (ja) |
KR (1) | KR101476468B1 (ja) |
CN (1) | CN101641386A (ja) |
ES (1) | ES2699625T3 (ja) |
MX (1) | MX2009008156A (ja) |
RU (1) | RU2467025C2 (ja) |
TR (1) | TR201821164T4 (ja) |
WO (2) | WO2008094238A1 (ja) |
Families Citing this family (20)
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US8193257B2 (en) | 2007-01-30 | 2012-06-05 | Dow Global Technologies Llc | Amine-initiated polyols and rigid polyurethane foam made therefrom |
WO2010009189A1 (en) * | 2008-07-16 | 2010-01-21 | Dow Global Technologies Inc. | Hydrogenation of aromatic polyols |
US20110124759A1 (en) * | 2008-07-30 | 2011-05-26 | Birch Adrian J | Polyol blends containing ortho-cyclohexanediamine-initiated polyols for rigid polyurethane foams |
CN102164978A (zh) * | 2008-07-30 | 2011-08-24 | 陶氏环球技术有限责任公司 | 基于邻-环己烷二胺引发的多元醇的硬质聚氨酯泡沫体系统 |
ITMI20081867A1 (it) * | 2008-10-22 | 2010-04-22 | Dow Global Technologies Inc | Processo per lapreparazione di schiume poliuretaniche rigide a celle chiuse |
US20110201707A1 (en) | 2008-11-10 | 2011-08-18 | Dow Global Technologies Llc | Isocyanate trimerisation catalyst system, a precursor formulation, a process for trimerising isocyanates, rigid polyisocyanurate/polyurethane foams made therefrom, and a process for making such foams |
MX2011010059A (es) * | 2009-03-24 | 2011-10-11 | Dow Global Technologies Llc | Produccion de espumas de poliuretano rigido y uso de las mismas. |
JP2013504656A (ja) * | 2009-09-09 | 2013-02-07 | アーケマ・インコーポレイテッド | ハロゲン化オレフィン発泡剤を使用した、改良されたポリウレタン発泡プロセス、およびフォームの性質 |
DE102009042971A1 (de) * | 2009-09-24 | 2011-09-15 | Clariant International Ltd. | Alkoxylierte cyclische Diamine und deren Verwendung als Emulsionsspalter |
CN102666627B (zh) * | 2009-09-29 | 2013-12-18 | 陶氏环球技术有限责任公司 | 包含1,3-和/或1,4-二(氨基甲基)环己烷-引发的多元醇以及亚甲基二(环己胺)-引发的多元醇和环己烷二胺-引发的至少一种多元醇的多元醇混合物、以及由其制得的聚氨酯 |
EP2386585B1 (en) | 2010-04-21 | 2017-03-22 | Dow Global Technologies LLC | Foam insulation unit |
US8673998B2 (en) | 2010-09-22 | 2014-03-18 | Bridgestone Corporation | Polymer compositions with improved cold flow |
WO2012040174A1 (en) * | 2010-09-24 | 2012-03-29 | Dow Global Technologies Llc | Non-aromatic based antioxidants for lubricants |
WO2012094514A1 (en) * | 2011-01-06 | 2012-07-12 | Bloom Energy Corporation | Sofc hot box components |
RU2579576C2 (ru) * | 2013-12-26 | 2016-04-10 | Лариса Владимировна Лучкина | Композиции для получения жестких пенополиуретанов теплоизоляционного назначения |
JP6287290B2 (ja) * | 2014-02-07 | 2018-03-07 | 東レ・ファインケミカル株式会社 | trans−1,2−ジアミノシクロヘキサンの製造方法 |
CN104262603A (zh) * | 2014-10-10 | 2015-01-07 | 天津工业大学 | 一种以聚醚胺为起始剂的聚醚破乳剂及其制备方法 |
CN108026247B (zh) | 2015-09-29 | 2022-03-25 | 陶氏环球技术有限责任公司 | 基于甲苯二异氰酸酯缩二脲的聚氨酯泡沫预聚物 |
TWI793073B (zh) | 2016-05-10 | 2023-02-21 | 美商陶氏全球科技有限責任公司 | 包括胺引發的多元醇的雙組分無溶劑黏著劑組合物 |
WO2021105336A1 (en) * | 2019-11-29 | 2021-06-03 | Basf Se | Compositions comprising polymer and enzyme |
Family Cites Families (14)
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US4595743A (en) * | 1985-01-22 | 1986-06-17 | The Dow Chemical Company | High modulus polyurea elastomers prepared with amine-initiated polyols |
US5114988A (en) * | 1989-10-23 | 1992-05-19 | Basf Corporation | Polyether polyols having reduced unsaturation and polyurethane foams prepared therefrom |
GB9022194D0 (en) | 1990-10-12 | 1990-11-28 | Ici Plc | Method for preparing polyurea-polyurethane flexible foams |
DE4200558A1 (de) * | 1992-01-11 | 1993-07-15 | Basf Ag | Verfahren zur herstellung von polyurethan-hartschaeumen sowie treibmittelmischung hierfuer |
CA2132595C (en) * | 1993-09-22 | 1999-03-16 | Thomas L. Fishback | Polyol composition having good flow and water blown rigid polyurethane foams made thereby having good dimensional stability |
US5426127A (en) * | 1994-09-26 | 1995-06-20 | Miles Inc. | Rigid foams with improved insulation and physical properties |
US5840212A (en) * | 1996-10-23 | 1998-11-24 | Bayer Corporation | Rigid foams with improved insulation properties and a process for the production of such foams |
IT1289472B1 (it) * | 1996-12-19 | 1998-10-15 | Manni S P A | Procedimento ed apparecchiatura per la schiumatura sottovuoto di pannelli isolanti,con insufflaggio di gas inerte |
DE19723193A1 (de) * | 1997-06-03 | 1998-12-10 | Bayer Ag | Verfahren zur Herstellung von geschlossenzelligen Polyurethan-Hartschaumstoffen mit geringer Wärmeleitfähigkeit |
CZ297662B6 (cs) * | 2001-05-21 | 2007-02-28 | Huntsman International Llc | Velmi mekký polyurethanový elastomer |
JP4132758B2 (ja) * | 2001-09-06 | 2008-08-13 | サンアプロ株式会社 | 新規アミジン化合物、その製造法、および使用法 |
US6562880B1 (en) * | 2002-04-17 | 2003-05-13 | Bayer Corporation | Polyurethane or polyisocyanurate foams blown with hydrofluorocarbons and carbon atoms |
KR101398244B1 (ko) * | 2005-11-14 | 2014-05-22 | 다우 글로벌 테크놀로지스 엘엘씨 | 향상된 열 전도성을 갖는 강성 폴리우레탄 발포체의 성형방법 |
US8193257B2 (en) * | 2007-01-30 | 2012-06-05 | Dow Global Technologies Llc | Amine-initiated polyols and rigid polyurethane foam made therefrom |
-
2007
- 2007-12-11 WO PCT/US2007/025290 patent/WO2008094238A1/en active Application Filing
-
2008
- 2008-01-30 EP EP08728511.0A patent/EP2115027B1/en active Active
- 2008-01-30 WO PCT/US2008/052396 patent/WO2008094963A1/en active Application Filing
- 2008-01-30 US US12/524,350 patent/US8318826B2/en active Active
- 2008-01-30 MX MX2009008156A patent/MX2009008156A/es active IP Right Grant
- 2008-01-30 ES ES08728511T patent/ES2699625T3/es active Active
- 2008-01-30 RU RU2009132507/04A patent/RU2467025C2/ru active
- 2008-01-30 JP JP2009548405A patent/JP5366829B2/ja active Active
- 2008-01-30 KR KR1020097017952A patent/KR101476468B1/ko active IP Right Grant
- 2008-01-30 TR TR2018/21164T patent/TR201821164T4/tr unknown
- 2008-01-30 CN CN200880009657A patent/CN101641386A/zh active Pending
Also Published As
Publication number | Publication date |
---|---|
WO2008094238A1 (en) | 2008-08-07 |
RU2009132507A (ru) | 2011-03-10 |
RU2467025C2 (ru) | 2012-11-20 |
JP2010516818A (ja) | 2010-05-20 |
MX2009008156A (es) | 2009-10-08 |
KR20090112736A (ko) | 2009-10-28 |
WO2008094963A1 (en) | 2008-08-07 |
CN101641386A (zh) | 2010-02-03 |
US20100298458A1 (en) | 2010-11-25 |
ES2699625T3 (es) | 2019-02-12 |
KR101476468B1 (ko) | 2014-12-24 |
US8318826B2 (en) | 2012-11-27 |
TR201821164T4 (tr) | 2019-01-21 |
EP2115027B1 (en) | 2018-10-03 |
EP2115027A1 (en) | 2009-11-11 |
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