JP2015520267A - 新規なカルボジイミド含有組成物、その合成方法、及びその使用 - Google Patents
新規なカルボジイミド含有組成物、その合成方法、及びその使用 Download PDFInfo
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- JP2015520267A JP2015520267A JP2015515426A JP2015515426A JP2015520267A JP 2015520267 A JP2015520267 A JP 2015520267A JP 2015515426 A JP2015515426 A JP 2015515426A JP 2015515426 A JP2015515426 A JP 2015515426A JP 2015520267 A JP2015520267 A JP 2015520267A
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- polyol
- carbodiimide
- diisocyanate
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- 0 *c(cc1*)cc(*)c1N=C=Nc1c(*)cc(*)cc1* Chemical compound *c(cc1*)cc(*)c1N=C=Nc1c(*)cc(*)cc1* 0.000 description 2
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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
- C08G18/02—Polymeric products of isocyanates or isothiocyanates of isocyanates or isothiocyanates only
- C08G18/025—Polymeric products of isocyanates or isothiocyanates of isocyanates or isothiocyanates only the polymeric products containing carbodiimide groups
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- C—CHEMISTRY; METALLURGY
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- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/0838—Manufacture of polymers in the presence of non-reactive compounds
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- C—CHEMISTRY; METALLURGY
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- 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
- C08G18/095—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 oligomerisation to carbodiimide or uretone-imine 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
- C08G18/28—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
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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
- C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
-
- 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
- C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
- C08G18/4244—Polycondensates having carboxylic or carbonic ester groups in the main chain containing oxygen in the form of ether 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
- C08G18/28—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
- C08G18/6633—Compounds of group C08G18/42
- C08G18/6637—Compounds of group C08G18/42 with compounds of group C08G18/32 or polyamines of C08G18/38
- C08G18/664—Compounds of group C08G18/42 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/3203
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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
- C08G18/65—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
- C08G18/6633—Compounds of group C08G18/42
- C08G18/6637—Compounds of group C08G18/42 with compounds of group C08G18/32 or polyamines of C08G18/38
- C08G18/6648—Compounds of group C08G18/42 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/3225 or C08G18/3271 and/or polyamines of C08G18/38
- C08G18/6651—Compounds of group C08G18/42 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/3225 or C08G18/3271 and/or polyamines of C08G18/38 with compounds of group C08G18/3225 or polyamines of C08G18/38
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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
- C08G71/00—Macromolecular compounds obtained by reactions forming a ureide or urethane link, otherwise, than from isocyanate radicals in the main chain of the macromolecule
- C08G71/04—Polyurethanes
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/22—Compounds containing nitrogen bound to another nitrogen atom
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/29—Compounds containing one or more carbon-to-nitrogen double bonds
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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
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/50—Physical properties
- C08G2261/59—Stability
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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)
- Engineering & Computer Science (AREA)
- Manufacturing & Machinery (AREA)
- Polyurethanes Or Polyureas (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
Description
(式中、R1、R2、R4及びR6はそれぞれ独立にC3〜C6アルキルであり、R3及びR5はそれぞれ独立にC1〜C3アルキルである)
のカルボジイミド化によって合成することができる。
との比較試験を、Bayer MaterialScience AG社のDesmophen(登録商標) 2001 KSタイプであるポリエステルポリオール中で行った。
焼き出し及び窒素充填を行った500mlのフランジ容器に、窒素を流した状態で400gの2,4,6−トリイソプロピルフェニルイソシアネートを最初に入れ、140℃に加熱した。400mgの1−メチルホスホレンオキシドを添加した後、反応混合物を5時間以内に160℃に加熱した。その後、NCO含量が<1%(変換率>95%に相当)になるまで160℃で反応を継続した。このようにして得られた粗生成物を蒸留によって精製した。得られた生成物は25℃で700mPasの粘度を有する淡黄色の液体であった。
熱安定性を調べるために、Mettler Toledo社のTGA分析ユニット(TGA/SDTA851)を用いて熱重量分析を行った。この目的のため、それぞれの試料10〜15mgを、昇温30〜600℃、加熱速度10℃/minで、窒素下で分析した。5%重量が減少した温度(℃)を測定した[T(5%)]。
Claims (15)
- 前記R1〜R6ラジカルが分子内で同じものであることを特徴とする、請求項1に記載の組成物。
- 前記R1〜R6ラジカルがイソプロピルであることを特徴とする、請求項1又は2に記載の組成物。
- 前記カルボジイミドが室温で液体であることを特徴とする、請求項1〜3のいずれか1項に記載の組成物。
- 前記カルボジイミドが前記式(I)のカルボジイミドの複数の混合物であることを特徴とする、請求項1〜4のいずれか1項に記載の組成物。
- 前記ポリオールが、ポリエステルポリオール及び/又はポリエーテルエステルポリオールを含むことを特徴とする、請求項1〜5のいずれか1項に記載の組成物。
- 前記ポリオールが、30〜80℃の温度で液体のポリエーテルエステルポリオール及び/又はポリエステルポリオールを含むことを特徴とする、請求項5に記載の組成物。
- 少なくとも1種の触媒を含有することを特徴とする、請求項1〜7のいずれか1項に記載の組成物。
- モル質量が200g/mol未満の少なくとも1種のジアミン及び/又は短鎖ジオールも更に含有することを特徴とする、請求項1〜8のいずれか1項に記載の組成物。
- 前記ポリオールが最初に入れられ、前記式(I)の液体カルボジイミド又は式(I)の液体カルボジイミドの混合物が撹拌しながら又は計量して入れられることを特徴とする、請求項4に記載の組成物の合成方法。
- ポリオールと少なくとも1種の式(I)のカルボジイミドとからなる組成物に、80〜130℃の温度でジイソシアネートが撹拌しながら入れられることを特徴とする、請求項1に記載の組成物の合成方法。
- 前記触媒が最初に、モル質量が200g/mol未満の前記ジアミン及び/又は前記短鎖ジオールと予め混合され、ポリオールと好ましくは液体カルボジイミドである少なくとも1種の式(I)のカルボジイミドと前記ジイソシアネートとからなる組成物に40〜100℃の温度で撹拌しながら入れられ、ポリオールに対するジイソシアネートの比率が20〜50:100重量部、より好ましくは25〜35:100重量部であることを特徴とする、請求項9に記載の組成物の合成方法。
- 請求項1〜9のいずれか1項に記載の組成物の、熱可塑性ポリウレタン中での使用。
- 請求項1〜9のいずれか1項に記載の組成物の、PUエラストマー、接着剤、注型用樹脂、又はPUフォーム中での使用。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
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EP12170770 | 2012-06-05 | ||
EP12170770.7 | 2012-06-05 | ||
PCT/EP2013/056157 WO2013182329A1 (de) | 2012-06-05 | 2013-03-22 | Neuartige carbodiimid-haltige zusammensetzungen, ein verfahren zu deren herstellung und deren verwendung |
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JP2015520267A true JP2015520267A (ja) | 2015-07-16 |
JP6174687B2 JP6174687B2 (ja) | 2017-08-02 |
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JP2015515426A Active JP6174687B2 (ja) | 2012-06-05 | 2013-03-22 | 新規なカルボジイミド含有組成物、その合成方法、及びその使用 |
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US (1) | US9434807B2 (ja) |
EP (1) | EP2855573B1 (ja) |
JP (1) | JP6174687B2 (ja) |
KR (1) | KR101983430B1 (ja) |
CN (1) | CN104334624B (ja) |
BR (1) | BR112014030549B1 (ja) |
CA (1) | CA2875737C (ja) |
ES (1) | ES2584556T3 (ja) |
MX (1) | MX364423B (ja) |
RU (1) | RU2014153664A (ja) |
WO (1) | WO2013182329A1 (ja) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN111471282A (zh) * | 2019-01-23 | 2020-07-31 | 朗盛德国有限责任公司 | 包含聚对苯二甲酸乙二醇酯和至少一种单体碳二亚胺的组合物及其生产方法和用途 |
WO2020196055A1 (ja) * | 2019-03-22 | 2020-10-01 | 日清紡ケミカル株式会社 | 粉体ポリカルボジイミド化合物及びエステル系樹脂組成物 |
JP2021505687A (ja) * | 2017-12-20 | 2021-02-18 | ランクセス・ドイチュランド・ゲーエムベーハー | カルボジイミドの製造方法 |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
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EP3502091A1 (de) | 2017-12-20 | 2019-06-26 | LANXESS Deutschland GmbH | Verfahren zur herstellung von carbodiimiden |
CN108912014A (zh) * | 2018-06-22 | 2018-11-30 | 上海朗亿功能材料有限公司 | 一种液体型碳化二亚胺化合物制备方法与应用 |
CN115651156A (zh) * | 2022-11-07 | 2023-01-31 | 合肥安利聚氨酯新材料有限公司 | 无溶剂聚氨酯树脂及其制备方法和应用 |
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- 2013-03-22 ES ES13711683.6T patent/ES2584556T3/es active Active
- 2013-03-22 MX MX2014014973A patent/MX364423B/es active IP Right Grant
- 2013-03-22 KR KR1020157000007A patent/KR101983430B1/ko active IP Right Grant
- 2013-03-22 RU RU2014153664A patent/RU2014153664A/ru unknown
- 2013-03-22 EP EP13711683.6A patent/EP2855573B1/de active Active
- 2013-03-22 JP JP2015515426A patent/JP6174687B2/ja active Active
- 2013-03-22 CA CA2875737A patent/CA2875737C/en active Active
- 2013-03-22 US US14/405,337 patent/US9434807B2/en active Active
- 2013-03-22 WO PCT/EP2013/056157 patent/WO2013182329A1/de active Application Filing
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JP2008004691A (ja) * | 2006-06-21 | 2008-01-10 | Toppan Printing Co Ltd | 太陽電池裏面封止用シート |
CN102816087A (zh) * | 2011-06-10 | 2012-12-12 | 上海朗亿功能材料有限公司 | 一种胶黏剂用水解稳定剂的制备方法 |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2021505687A (ja) * | 2017-12-20 | 2021-02-18 | ランクセス・ドイチュランド・ゲーエムベーハー | カルボジイミドの製造方法 |
JP7052066B2 (ja) | 2017-12-20 | 2022-04-11 | ランクセス・ドイチュランド・ゲーエムベーハー | カルボジイミドの製造方法 |
CN111471282A (zh) * | 2019-01-23 | 2020-07-31 | 朗盛德国有限责任公司 | 包含聚对苯二甲酸乙二醇酯和至少一种单体碳二亚胺的组合物及其生产方法和用途 |
JP2020117698A (ja) * | 2019-01-23 | 2020-08-06 | ランクセス・ドイチュランド・ゲーエムベーハー | ポリエチレンテレフタレート(pet)を含む耐加水分解性組成物 |
WO2020196055A1 (ja) * | 2019-03-22 | 2020-10-01 | 日清紡ケミカル株式会社 | 粉体ポリカルボジイミド化合物及びエステル系樹脂組成物 |
Also Published As
Publication number | Publication date |
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CA2875737C (en) | 2019-09-24 |
US9434807B2 (en) | 2016-09-06 |
KR101983430B1 (ko) | 2019-05-28 |
WO2013182329A1 (de) | 2013-12-12 |
CN104334624A (zh) | 2015-02-04 |
US20150166714A1 (en) | 2015-06-18 |
BR112014030549A2 (pt) | 2017-06-27 |
EP2855573B1 (de) | 2016-05-18 |
BR112014030549B1 (pt) | 2020-11-03 |
ES2584556T3 (es) | 2016-09-28 |
CA2875737A1 (en) | 2013-12-12 |
EP2855573A1 (de) | 2015-04-08 |
JP6174687B2 (ja) | 2017-08-02 |
RU2014153664A (ru) | 2016-07-27 |
MX364423B (es) | 2019-04-25 |
KR20150023616A (ko) | 2015-03-05 |
MX2014014973A (es) | 2015-07-14 |
CN104334624B (zh) | 2016-08-17 |
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