KR20100099713A - 폴리(트라이메틸렌 글리콜 카보네이트 트라이메틸렌 글리콜 에테르) 다이올 조성물 및 이의 제조 방법 - Google Patents
폴리(트라이메틸렌 글리콜 카보네이트 트라이메틸렌 글리콜 에테르) 다이올 조성물 및 이의 제조 방법 Download PDFInfo
- Publication number
- KR20100099713A KR20100099713A KR1020107014391A KR20107014391A KR20100099713A KR 20100099713 A KR20100099713 A KR 20100099713A KR 1020107014391 A KR1020107014391 A KR 1020107014391A KR 20107014391 A KR20107014391 A KR 20107014391A KR 20100099713 A KR20100099713 A KR 20100099713A
- Authority
- KR
- South Korea
- Prior art keywords
- trimethylene glycol
- poly
- carbonate
- trimethylene
- glycol ether
- 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.)
- Withdrawn
Links
- -1 poly(trimethylene glycol carbonate trimethylene glycol Chemical compound 0.000 title claims abstract description 25
- 238000000034 method Methods 0.000 title claims abstract description 24
- 150000002009 diols Chemical class 0.000 title claims abstract description 23
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 title claims abstract description 23
- 239000000203 mixture Substances 0.000 title claims abstract description 9
- 239000002904 solvent Substances 0.000 claims abstract description 20
- 239000003456 ion exchange resin Substances 0.000 claims abstract description 12
- 229920003303 ion-exchange polymer Polymers 0.000 claims abstract description 12
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims abstract description 9
- 230000002378 acidificating effect Effects 0.000 claims abstract description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 35
- 239000003054 catalyst Substances 0.000 claims description 27
- YFHICDDUDORKJB-UHFFFAOYSA-N trimethylene carbonate Chemical compound O=C1OCCCO1 YFHICDDUDORKJB-UHFFFAOYSA-N 0.000 claims description 24
- 125000001424 substituent group Chemical group 0.000 claims description 16
- 125000004122 cyclic group Chemical group 0.000 claims description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 12
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 125000006737 (C6-C20) arylalkyl group Chemical group 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 claims description 4
- 229920001577 copolymer Polymers 0.000 claims description 4
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 229920000172 poly(styrenesulfonic acid) Polymers 0.000 claims 1
- 239000011973 solid acid Substances 0.000 claims 1
- 125000003944 tolyl group Chemical group 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 6
- 229920000557 Nafion® Polymers 0.000 description 24
- 239000000463 material Substances 0.000 description 18
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 14
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 11
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 11
- 229940035437 1,3-propanediol Drugs 0.000 description 11
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Chemical group C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 9
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 7
- 239000000376 reactant Substances 0.000 description 7
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical group C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 5
- 238000005481 NMR spectroscopy Methods 0.000 description 4
- 238000002835 absorbance Methods 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- PMPVIKIVABFJJI-UHFFFAOYSA-N Cyclobutane Chemical group C1CCC1 PMPVIKIVABFJJI-UHFFFAOYSA-N 0.000 description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical group C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 3
- WJTCGQSWYFHTAC-UHFFFAOYSA-N cyclooctane Chemical group C1CCCCCCC1 WJTCGQSWYFHTAC-UHFFFAOYSA-N 0.000 description 3
- 239000004914 cyclooctane Chemical group 0.000 description 3
- 229920000515 polycarbonate Polymers 0.000 description 3
- 239000004417 polycarbonate Substances 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 239000011550 stock solution Substances 0.000 description 3
- 102000004882 Lipase Human genes 0.000 description 2
- 108090001060 Lipase Proteins 0.000 description 2
- 239000004367 Lipase Substances 0.000 description 2
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- 238000002306 biochemical method Methods 0.000 description 2
- 239000000560 biocompatible material Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 235000019421 lipase Nutrition 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- 229920002635 polyurethane Polymers 0.000 description 2
- 239000004814 polyurethane Substances 0.000 description 2
- 238000010926 purge Methods 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- YHRUOJUYPBUZOS-UHFFFAOYSA-N 1,3-dichloropropane Chemical compound ClCCCCl YHRUOJUYPBUZOS-UHFFFAOYSA-N 0.000 description 1
- LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical compound C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000010538 cationic polymerization reaction Methods 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000000113 differential scanning calorimetry Methods 0.000 description 1
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 229920000554 ionomer Polymers 0.000 description 1
- 238000010667 large scale reaction Methods 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- VSPPONOIKZXUBJ-UHFFFAOYSA-N n,n-diethylethanamine;oxolane Chemical compound C1CCOC1.CCN(CC)CC VSPPONOIKZXUBJ-UHFFFAOYSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000003303 reheating Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000002076 thermal analysis method Methods 0.000 description 1
- 150000003606 tin compounds Chemical class 0.000 description 1
- 239000012780 transparent material 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
- C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
- C08G64/02—Aliphatic polycarbonates
- C08G64/0208—Aliphatic polycarbonates saturated
-
- 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
- C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
- C08G64/20—General preparatory processes
- C08G64/30—General preparatory processes using carbonates
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyesters Or Polycarbonates (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US99169407P | 2007-11-30 | 2007-11-30 | |
| US60/991,694 | 2007-11-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20100099713A true KR20100099713A (ko) | 2010-09-13 |
Family
ID=40351552
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020107014391A Withdrawn KR20100099713A (ko) | 2007-11-30 | 2008-11-25 | 폴리(트라이메틸렌 글리콜 카보네이트 트라이메틸렌 글리콜 에테르) 다이올 조성물 및 이의 제조 방법 |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US20090143624A1 (enExample) |
| EP (1) | EP2215143A1 (enExample) |
| JP (1) | JP2011505469A (enExample) |
| KR (1) | KR20100099713A (enExample) |
| CN (1) | CN101878246A (enExample) |
| AU (1) | AU2008329782A1 (enExample) |
| CA (1) | CA2704028A1 (enExample) |
| MX (1) | MX2010005760A (enExample) |
| TW (1) | TW200932781A (enExample) |
| WO (1) | WO2009070591A1 (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2008329778A1 (en) * | 2007-11-30 | 2009-06-04 | E. I. Du Pont De Nemours And Company | Solventless processes for the polymerization of a trimethylene carbonate to a poly(trimethylene glycol carbonate trimethylene glycol ether) diol |
| WO2009070578A1 (en) * | 2007-11-30 | 2009-06-04 | E. I. Du Pont De Nemours And Company | Copolymers comprising a trimethylene carbonate and poly(trimethylene ether) glycols |
| JP5455407B2 (ja) | 2009-03-25 | 2014-03-26 | 日本ゴア株式会社 | 触媒粒子を担持した延伸ポリテトラフルオロエチレン多孔質膜またはテープの製造方法およびオゾン除去用フィルタ |
| US9484568B2 (en) | 2010-10-20 | 2016-11-01 | Sintokogio, Ltd. | Method of manufacturing layered structure constituting all-solid-state battery, apparatus for manufacturing the same, and all-solid-state battery provided with layered structure |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3624053A (en) * | 1963-06-24 | 1971-11-30 | Du Pont | Trifluorovinyl sulfonic acid polymers |
| US3301824A (en) * | 1963-09-26 | 1967-01-31 | Union Carbide Corp | Polymers of cyclic carbonates |
| US3379693A (en) * | 1964-05-28 | 1968-04-23 | Union Carbide Corp | Carbonate compositions |
| US5124299A (en) * | 1989-08-02 | 1992-06-23 | E. I. Du Pont De Nemours And Company | Catalysis using blends of perfluorinated ion-exchange polymers with perfluorinated diluents |
| JPH0710920A (ja) * | 1992-12-01 | 1995-01-13 | Nippon Paint Co Ltd | 環状カーボネート化合物のアルコール性水酸基への開環付加方法 |
| US6451949B2 (en) * | 2000-02-29 | 2002-09-17 | Shell Oil Company | Method for production of poly (trimethylene carbonate) |
| WO2003016298A2 (en) * | 2001-08-17 | 2003-02-27 | Ucb, S.A. | Process for making a compound containing cyclic and linear carbonate groups |
| CA2703786A1 (en) * | 2007-11-30 | 2009-06-04 | E.I. Du Pont De Nemours And Company | Process to make a poly(trimethylene carbonate) glycol |
| AU2008329778A1 (en) * | 2007-11-30 | 2009-06-04 | E. I. Du Pont De Nemours And Company | Solventless processes for the polymerization of a trimethylene carbonate to a poly(trimethylene glycol carbonate trimethylene glycol ether) diol |
-
2008
- 2008-11-25 KR KR1020107014391A patent/KR20100099713A/ko not_active Withdrawn
- 2008-11-25 CN CN2008801183110A patent/CN101878246A/zh active Pending
- 2008-11-25 AU AU2008329782A patent/AU2008329782A1/en not_active Abandoned
- 2008-11-25 MX MX2010005760A patent/MX2010005760A/es unknown
- 2008-11-25 WO PCT/US2008/084704 patent/WO2009070591A1/en not_active Ceased
- 2008-11-25 JP JP2010536132A patent/JP2011505469A/ja not_active Abandoned
- 2008-11-25 US US12/277,655 patent/US20090143624A1/en not_active Abandoned
- 2008-11-25 EP EP08855519A patent/EP2215143A1/en not_active Withdrawn
- 2008-11-25 CA CA2704028A patent/CA2704028A1/en not_active Abandoned
- 2008-11-28 TW TW097146511A patent/TW200932781A/zh unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AU2008329782A1 (en) | 2009-06-04 |
| WO2009070591A1 (en) | 2009-06-04 |
| MX2010005760A (es) | 2010-06-11 |
| EP2215143A1 (en) | 2010-08-11 |
| CN101878246A (zh) | 2010-11-03 |
| CA2704028A1 (en) | 2009-06-04 |
| JP2011505469A (ja) | 2011-02-24 |
| TW200932781A (en) | 2009-08-01 |
| US20090143624A1 (en) | 2009-06-04 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PA0105 | International application |
Patent event date: 20100629 Patent event code: PA01051R01D Comment text: International Patent Application |
|
| PG1501 | Laying open of application | ||
| PC1203 | Withdrawal of no request for examination | ||
| WITN | Application deemed withdrawn, e.g. because no request for examination was filed or no examination fee was paid |