KR100564874B1 - 옥시테트라메틸렌글리콜 공중합체 및 그의 제조 방법 - Google Patents
옥시테트라메틸렌글리콜 공중합체 및 그의 제조 방법 Download PDFInfo
- Publication number
- KR100564874B1 KR100564874B1 KR20037009278A KR20037009278A KR100564874B1 KR 100564874 B1 KR100564874 B1 KR 100564874B1 KR 20037009278 A KR20037009278 A KR 20037009278A KR 20037009278 A KR20037009278 A KR 20037009278A KR 100564874 B1 KR100564874 B1 KR 100564874B1
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- KR
- South Korea
- Prior art keywords
- molecular weight
- glycol copolymer
- oxytetramethylene glycol
- reaction
- thf
- 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 - Lifetime
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- 229920001577 copolymer Polymers 0.000 title claims abstract description 359
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- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 title claims abstract description 290
- 238000002360 preparation method Methods 0.000 title abstract description 7
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims abstract description 601
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims abstract description 296
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 claims abstract description 219
- 238000007334 copolymerization reaction Methods 0.000 claims abstract description 152
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- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 8
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- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 6
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- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
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- 238000005160 1H NMR spectroscopy Methods 0.000 description 5
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 5
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- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 4
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- 239000000945 filler Substances 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- SXCBDZAEHILGLM-UHFFFAOYSA-N heptane-1,7-diol Chemical compound OCCCCCCCO SXCBDZAEHILGLM-UHFFFAOYSA-N 0.000 description 1
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 description 1
- AVIYEYCFMVPYST-UHFFFAOYSA-N hexane-1,3-diol Chemical compound CCCC(O)CCO AVIYEYCFMVPYST-UHFFFAOYSA-N 0.000 description 1
- QVTWBMUAJHVAIJ-UHFFFAOYSA-N hexane-1,4-diol Chemical compound CCC(O)CCCO QVTWBMUAJHVAIJ-UHFFFAOYSA-N 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- 238000001095 inductively coupled plasma mass spectrometry Methods 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- 230000009878 intermolecular interaction Effects 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- OEIJHBUUFURJLI-UHFFFAOYSA-N octane-1,8-diol Chemical compound OCCCCCCCCO OEIJHBUUFURJLI-UHFFFAOYSA-N 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920005749 polyurethane resin Polymers 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 238000005057 refrigeration Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 239000010421 standard material Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000002436 steel type Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
Images
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
- 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
- C08G65/30—Post-polymerisation treatment, e.g. recovery, purification, drying
-
- 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
- C08G65/04—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 only
- C08G65/06—Cyclic ethers having no atoms other than carbon and hydrogen outside the ring
- C08G65/16—Cyclic ethers having four or more ring atoms
- C08G65/20—Tetrahydrofuran
-
- 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
- C08G65/2603—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 oxygen
- C08G65/2606—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 oxygen containing hydroxyl groups
- C08G65/2609—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 oxygen containing hydroxyl groups containing aliphatic hydroxyl 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
- C08G65/2696—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 characterised by the process or apparatus used
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyethers (AREA)
- Polyesters Or Polycarbonates (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2001003899 | 2001-01-11 | ||
| JPJP-P-2001-00003899 | 2001-01-11 | ||
| JP2001003810 | 2001-01-11 | ||
| JPJP-P-2001-00003810 | 2001-01-11 | ||
| PCT/JP2001/003230 WO2002055586A1 (fr) | 2001-01-11 | 2001-04-16 | Copolymere d'oxytetramethylene glycol et son procede de production |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR20030068207A KR20030068207A (ko) | 2003-08-19 |
| KR100564874B1 true KR100564874B1 (ko) | 2006-03-30 |
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| EP (1) | EP1361243B1 (enExample) |
| JP (1) | JP4901061B2 (enExample) |
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| AT (1) | ATE489418T1 (enExample) |
| CA (1) | CA2433731C (enExample) |
| DE (1) | DE60143547D1 (enExample) |
| TW (1) | TWI296632B (enExample) |
| WO (1) | WO2002055586A1 (enExample) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| TWI296632B (enExample) * | 2001-01-11 | 2008-05-11 | Asahi Chemical Ind | |
| DE10259136A1 (de) * | 2002-12-18 | 2004-07-01 | Basf Ag | Verfahren zur Herstellung von Tetrahydrofuran-Copolymeren |
| DE10314648A1 (de) * | 2003-04-01 | 2004-10-14 | Basf Ag | Verfahren zur Herstellung von Tetrahydrofuran-Copolymeren |
| DE10314649A1 (de) * | 2003-04-01 | 2004-10-14 | Basf Ag | Verfahren zur Herstellung von Tetrahydrofuran-Copolymeren |
| TW201029967A (en) * | 2009-02-13 | 2010-08-16 | Nanya Plastics Corp | Method for preparing hindered phenol type antioxidant |
| CN111855864B (zh) * | 2020-08-17 | 2023-01-10 | 青岛科技大学 | 二甲环丙醚及新戊二醇的气相色谱分析方法 |
| CN113087893B (zh) * | 2021-03-23 | 2023-04-28 | 杭州三隆新材料有限公司 | 一种四氢呋喃共聚物及其制备方法 |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0158229B1 (en) * | 1984-03-28 | 1988-06-22 | Asahi Kasei Kogyo Kabushiki Kaisha | Process for producing polyether polyol, the produced polyether polyol and polyurethane |
| CA1268481A (en) * | 1984-11-13 | 1990-05-01 | Atsushi Aoshima | Process for purification of polyether |
| JPS61126134A (ja) | 1984-11-22 | 1986-06-13 | Asahi Chem Ind Co Ltd | ポリアルキレンエ−テルポリオ−ルを製造する方法 |
| DE3606479A1 (de) * | 1986-02-28 | 1987-09-03 | Basf Ag | Verfahren zur herstellung von polyoxibutylenpolyoxialkylenglykolen mit enger molekulargewichtsverteilung und vermindertem gehalt an oligomeren cyclischen ethern |
| JP4395203B2 (ja) | 1996-04-10 | 2010-01-06 | 旭化成せんい株式会社 | ポリエーテルジオールの製造方法 |
| JP3747961B2 (ja) * | 1996-04-24 | 2006-02-22 | 旭化成せんい株式会社 | ポリエーテルポリオール中のジオールの回収法 |
| JPH1087813A (ja) | 1996-09-12 | 1998-04-07 | Asahi Chem Ind Co Ltd | 共重合ポリエーテルポリオールの精製方法 |
| JP3932145B2 (ja) | 1996-09-20 | 2007-06-20 | 旭化成せんい株式会社 | 共重合ポリエーテルポリオールの製造方法 |
| JP2000044671A (ja) * | 1998-05-26 | 2000-02-15 | Asahi Chem Ind Co Ltd | ポリエ―テルグリコ―ルの分子量分布の制御方法 |
| WO1999061507A1 (fr) * | 1998-05-26 | 1999-12-02 | Asahi Kasei Kogyo Kabushiki Kaisha | Procede de regulation de la repartition des poids moleculaires du glycol de polyether |
| JP4194011B2 (ja) * | 1999-08-19 | 2008-12-10 | 旭化成せんい株式会社 | ポリテトラメチレングリコール組成物 |
| DE10103548A1 (de) * | 2000-01-28 | 2001-09-06 | Asahi Chemical Ind | Thermoplastische Elastomerzusammensetzung |
| TWI296632B (enExample) * | 2001-01-11 | 2008-05-11 | Asahi Chemical Ind |
-
2001
- 2001-04-16 TW TW090109216A patent/TWI296632B/zh not_active IP Right Cessation
- 2001-04-16 DE DE60143547T patent/DE60143547D1/de not_active Expired - Lifetime
- 2001-04-16 AT AT01919942T patent/ATE489418T1/de not_active IP Right Cessation
- 2001-04-16 WO PCT/JP2001/003230 patent/WO2002055586A1/ja not_active Ceased
- 2001-04-16 KR KR20037009278A patent/KR100564874B1/ko not_active Expired - Lifetime
- 2001-04-16 CN CNB018219284A patent/CN1272362C/zh not_active Expired - Lifetime
- 2001-04-16 EP EP01919942A patent/EP1361243B1/en not_active Expired - Lifetime
- 2001-04-16 US US10/250,859 patent/US7217783B2/en not_active Expired - Lifetime
- 2001-04-16 CA CA002433731A patent/CA2433731C/en not_active Expired - Fee Related
- 2001-04-16 JP JP2002556649A patent/JP4901061B2/ja not_active Expired - Lifetime
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2007
- 2007-04-02 US US11/730,523 patent/US7485696B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| US7485696B2 (en) | 2009-02-03 |
| WO2002055586A1 (fr) | 2002-07-18 |
| EP1361243A1 (en) | 2003-11-12 |
| US20040049007A1 (en) | 2004-03-11 |
| JPWO2002055586A1 (ja) | 2004-05-13 |
| CN1486337A (zh) | 2004-03-31 |
| CA2433731C (en) | 2009-11-10 |
| US7217783B2 (en) | 2007-05-15 |
| ATE489418T1 (de) | 2010-12-15 |
| KR20030068207A (ko) | 2003-08-19 |
| CA2433731A1 (en) | 2002-07-18 |
| CN1272362C (zh) | 2006-08-30 |
| EP1361243B1 (en) | 2010-11-24 |
| EP1361243A4 (en) | 2007-09-12 |
| JP4901061B2 (ja) | 2012-03-21 |
| US20070173631A1 (en) | 2007-07-26 |
| TWI296632B (enExample) | 2008-05-11 |
| DE60143547D1 (de) | 2011-01-05 |
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