TWI500694B - 可熔融加工之共聚醚醯胺彈性體及其製法 - Google Patents
可熔融加工之共聚醚醯胺彈性體及其製法 Download PDFInfo
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- TWI500694B TWI500694B TW100106362A TW100106362A TWI500694B TW I500694 B TWI500694 B TW I500694B TW 100106362 A TW100106362 A TW 100106362A TW 100106362 A TW100106362 A TW 100106362A TW I500694 B TWI500694 B TW I500694B
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- Taiwan
- Prior art keywords
- diisocyanate
- terminated
- caprolactam
- monomer
- elastomer
- Prior art date
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- 229920001971 elastomer Polymers 0.000 title claims description 70
- 239000000806 elastomer Substances 0.000 title claims description 70
- 238000000034 method Methods 0.000 title claims description 29
- 125000005442 diisocyanate group Chemical group 0.000 claims description 93
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 claims description 66
- 239000000178 monomer Substances 0.000 claims description 60
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- -1 poly(tetrahydrofuran) Polymers 0.000 claims description 28
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- 238000010438 heat treatment Methods 0.000 description 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
- GPCIDUIBGGUBJG-UHFFFAOYSA-N hexanedioic acid;hexane-1,1-diol Chemical compound CCCCCC(O)O.OC(=O)CCCCC(O)=O GPCIDUIBGGUBJG-UHFFFAOYSA-N 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- YOBAEOGBNPPUQV-UHFFFAOYSA-N iron;trihydrate Chemical compound O.O.O.[Fe].[Fe] YOBAEOGBNPPUQV-UHFFFAOYSA-N 0.000 description 1
- LADVLFVCTCHOAI-UHFFFAOYSA-N isocyanic acid;toluene Chemical compound N=C=O.CC1=CC=CC=C1 LADVLFVCTCHOAI-UHFFFAOYSA-N 0.000 description 1
- 239000011968 lewis acid catalyst Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 229960005336 magnesium citrate Drugs 0.000 description 1
- 235000002538 magnesium citrate Nutrition 0.000 description 1
- 239000004337 magnesium citrate Substances 0.000 description 1
- 229940091250 magnesium supplement Drugs 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- KBOPZPXVLCULAV-UHFFFAOYSA-N mesalamine Chemical compound NC1=CC=C(O)C(C(O)=O)=C1 KBOPZPXVLCULAV-UHFFFAOYSA-N 0.000 description 1
- 229960004963 mesalazine Drugs 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 229910003455 mixed metal oxide Inorganic materials 0.000 description 1
- 238000003541 multi-stage reaction Methods 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-N o-dicarboxybenzene Natural products OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000003605 opacifier Substances 0.000 description 1
- 239000012860 organic pigment Substances 0.000 description 1
- BMMGVYCKOGBVEV-UHFFFAOYSA-N oxo(oxoceriooxy)cerium Chemical compound [Ce]=O.O=[Ce]=O BMMGVYCKOGBVEV-UHFFFAOYSA-N 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- VSIIXMUUUJUKCM-UHFFFAOYSA-D pentacalcium;fluoride;triphosphate Chemical compound [F-].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O VSIIXMUUUJUKCM-UHFFFAOYSA-D 0.000 description 1
- LPXCHPSTROLSJX-UHFFFAOYSA-N pentanimidamide Chemical compound CCCCC(N)=N LPXCHPSTROLSJX-UHFFFAOYSA-N 0.000 description 1
- 239000002530 phenolic antioxidant Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 239000003504 photosensitizing agent Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 1
- 229940080818 propionamide Drugs 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- FIWQZURFGYXCEO-UHFFFAOYSA-M sodium;decanoate Chemical compound [Na+].CCCCCCCCCC([O-])=O FIWQZURFGYXCEO-UHFFFAOYSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 229920006345 thermoplastic polyamide Polymers 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 150000007944 thiolates Chemical class 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- PLSARIKBYIPYPF-UHFFFAOYSA-H trimagnesium dicitrate Chemical compound [Mg+2].[Mg+2].[Mg+2].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O.[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O PLSARIKBYIPYPF-UHFFFAOYSA-H 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
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
- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
- C08G69/40—Polyamides 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
- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
- C08G18/4854—Polyethers containing oxyalkylene groups having four carbon atoms in the alkylene 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
- C08G18/8061—Masked polyisocyanates masked with compounds having only one group containing active hydrogen
- C08G18/807—Masked polyisocyanates masked with compounds having only one group containing active hydrogen with nitrogen containing compounds
- C08G18/8074—Lactams
-
- 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
- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
- C08G69/02—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids
- C08G69/08—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from amino-carboxylic acids
- C08G69/14—Lactams
-
- 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
- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
- C08G69/02—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids
- C08G69/08—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from amino-carboxylic acids
- C08G69/14—Lactams
- C08G69/16—Preparatory processes
- C08G69/18—Anionic polymerisation
-
- 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
- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
- C08G69/02—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids
- C08G69/08—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from amino-carboxylic acids
- C08G69/14—Lactams
- C08G69/16—Preparatory processes
- C08G69/18—Anionic polymerisation
- C08G69/20—Anionic polymerisation characterised by the catalysts used
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L77/00—Compositions of polyamides obtained by reactions forming a carboxylic amide link in the main chain; Compositions of derivatives of such polymers
- C08L77/02—Polyamides derived from omega-amino carboxylic acids or from lactams thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyamides (AREA)
- Polyurethanes Or Polyureas (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US30907610P | 2010-03-01 | 2010-03-01 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| TW201137034A TW201137034A (en) | 2011-11-01 |
| TWI500694B true TWI500694B (zh) | 2015-09-21 |
Family
ID=43972726
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW100106362A TWI500694B (zh) | 2010-03-01 | 2011-02-25 | 可熔融加工之共聚醚醯胺彈性體及其製法 |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US8722794B2 (OSRAM) |
| EP (1) | EP2542603B1 (OSRAM) |
| JP (2) | JP6084465B2 (OSRAM) |
| CN (1) | CN102781991B (OSRAM) |
| CA (1) | CA2790565C (OSRAM) |
| ES (1) | ES2844323T3 (OSRAM) |
| HU (1) | HUE053245T2 (OSRAM) |
| TW (1) | TWI500694B (OSRAM) |
| WO (1) | WO2011109211A1 (OSRAM) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9139752B2 (en) * | 2011-09-28 | 2015-09-22 | Basf Se | Process for producing polyamides via anionic polymerization |
| CN104497570A (zh) * | 2014-12-17 | 2015-04-08 | 江门市优巨新材料有限公司 | 一种耐高温无卤阻燃尼龙复合材料及其制备方法 |
| US10875962B2 (en) * | 2016-03-08 | 2020-12-29 | Invista North America S.A.R.L. | Polyamide copolymer and method of making the same |
| CN107936255B (zh) * | 2017-11-01 | 2021-03-02 | 中纺院（天津）科技发展有限公司 | 一种连续生产聚醚酰胺的方法 |
| CN112210076B (zh) * | 2019-07-11 | 2023-08-15 | 中国石油化工股份有限公司 | 一种连续化生产聚醚酰胺弹性体的方法及装置 |
| EP4004084B1 (de) | 2019-07-31 | 2023-09-06 | Basf Se | Neue blockcopolymere |
| CN112724660B (zh) * | 2020-12-28 | 2023-06-13 | 晋江市创达鞋业有限公司 | 轻量抗疲劳peba鞋底及其成型工艺 |
| CN114196193B (zh) * | 2021-11-19 | 2024-02-23 | 美瑞新材料股份有限公司 | 一种基于阴离子聚合制备尼龙弹性体的连续生产方法 |
| CN116120563B (zh) * | 2023-01-03 | 2024-06-25 | 万华化学集团股份有限公司 | 一种基于动态双硫键的热适应性聚醚酰胺弹性体材料及其制备方法 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4540516A (en) * | 1983-08-20 | 1985-09-10 | Stamicarbon B.V., Licensing Subsidiary Of Dsm | Process for the preparation of an N-substituted carbamoyl-lactam compound |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3993709A (en) | 1974-06-24 | 1976-11-23 | Monsanto Company | Polyester initiated anionic catalyzed polymerization of lactam |
| JPS59157121A (ja) * | 1983-02-25 | 1984-09-06 | Kanebo Ltd | 強化ポリアミドシ−トの製造法 |
| DE3469360D1 (en) | 1983-08-20 | 1988-03-24 | Stamicarbon | Process for the preparation of an n-substituted carbamoyllactam compound |
| NL8302928A (nl) * | 1983-08-20 | 1985-03-18 | Stamicarbon | N-gesubstitueerde carbamoyl-lactam verbinding. |
| NL8400006A (nl) * | 1984-01-03 | 1985-08-01 | Stamicarbon | Werkwijze voor de condensatie van imide en alkohol. |
| NL8400411A (nl) * | 1984-02-09 | 1985-09-02 | Stamicarbon | Werkwijze voor het bereiden van een nylonblokcopolymeercompositie. |
| KR870001407B1 (ko) * | 1984-03-22 | 1987-07-30 | 스태미카본 베· 뷔 | N-치환된 카로바모일-락탐 화합물의 제조방법 |
| US4614615A (en) * | 1984-03-22 | 1986-09-30 | Kaneyoshi Ashida | Process for preparing an N-substituted carbamoyl-lactam compound |
| US4626385A (en) * | 1984-03-22 | 1986-12-02 | Kaneyoshi Ashida | N-substituted carbamoyl-lactam |
| US4673722A (en) | 1985-12-23 | 1987-06-16 | General Motors Corporation | High impact nylon/polyurea copolymer |
| NL8702950A (nl) * | 1987-12-08 | 1989-07-03 | Stamicarbon | Werkwijze voor het bereiden van een nylonblokcopolymeer. |
| NL8801914A (nl) | 1988-07-30 | 1990-02-16 | Stamicarbon | Omzettingsprodukten van met lactam geblokkeerde diisocyanaten en daarvan afgeleide polylactamblokcopolymeren. |
| DE4203297A1 (de) * | 1992-01-31 | 1993-08-05 | Fischer Karl Ind Gmbh | Verfahren zur herstellung von polyurethan- und/oder polyurethanharnstoff-elastomer |
| JPH06116385A (ja) * | 1992-10-02 | 1994-04-26 | Toray Ind Inc | 中空成形品の製造方法 |
| BE1006638A3 (nl) * | 1993-01-27 | 1994-11-03 | Dsm Nv | Werkwijze voor het bereiden van een nylonblokcopolymeer. |
| JPH0732390A (ja) * | 1993-07-15 | 1995-02-03 | Toray Ind Inc | 中空成形品の製造方法 |
| JP3838622B2 (ja) * | 2001-04-05 | 2006-10-25 | 日本ポリペンコ株式会社 | ポリアミドエラストマー成形体及びその製造方法 |
| JP2005336354A (ja) * | 2004-05-27 | 2005-12-08 | Nippon Polypenco Ltd | ポリアミドエラストマー成形体及びその製造方法。 |
-
2011
- 2011-02-24 ES ES11707743T patent/ES2844323T3/es active Active
- 2011-02-24 JP JP2012556110A patent/JP6084465B2/ja active Active
- 2011-02-24 US US13/034,014 patent/US8722794B2/en active Active
- 2011-02-24 CA CA2790565A patent/CA2790565C/en not_active Expired - Fee Related
- 2011-02-24 CN CN201180011676.5A patent/CN102781991B/zh active Active
- 2011-02-24 EP EP11707743.8A patent/EP2542603B1/en active Active
- 2011-02-24 HU HUE11707743A patent/HUE053245T2/hu unknown
- 2011-02-24 WO PCT/US2011/026018 patent/WO2011109211A1/en not_active Ceased
- 2011-02-25 TW TW100106362A patent/TWI500694B/zh active
-
2016
- 2016-06-15 JP JP2016118660A patent/JP2016164282A/ja not_active Withdrawn
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4540516A (en) * | 1983-08-20 | 1985-09-10 | Stamicarbon B.V., Licensing Subsidiary Of Dsm | Process for the preparation of an N-substituted carbamoyl-lactam compound |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2011109211A1 (en) | 2011-09-09 |
| JP2013521373A (ja) | 2013-06-10 |
| HUE053245T2 (hu) | 2021-06-28 |
| EP2542603A1 (en) | 2013-01-09 |
| JP6084465B2 (ja) | 2017-02-22 |
| ES2844323T3 (es) | 2021-07-21 |
| CA2790565A1 (en) | 2011-09-09 |
| TW201137034A (en) | 2011-11-01 |
| CA2790565C (en) | 2018-04-03 |
| US20110213076A1 (en) | 2011-09-01 |
| EP2542603B1 (en) | 2020-11-18 |
| JP2016164282A (ja) | 2016-09-08 |
| CN102781991B (zh) | 2015-07-29 |
| CN102781991A (zh) | 2012-11-14 |
| US8722794B2 (en) | 2014-05-13 |
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