TW200932781A - Compositions of and processes for producing a poly (trimethylene glycol carbonate trimethylene glycol ether) diol - Google Patents
Compositions of and processes for producing a poly (trimethylene glycol carbonate trimethylene glycol ether) diol Download PDFInfo
- Publication number
- TW200932781A TW200932781A TW097146511A TW97146511A TW200932781A TW 200932781 A TW200932781 A TW 200932781A TW 097146511 A TW097146511 A TW 097146511A TW 97146511 A TW97146511 A TW 97146511A TW 200932781 A TW200932781 A TW 200932781A
- Authority
- TW
- Taiwan
- Prior art keywords
- propylene glycol
- poly
- carbonate
- group
- substituent
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 29
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 title claims abstract description 19
- 150000002009 diols Chemical class 0.000 title claims abstract description 15
- -1 poly (trimethylene glycol carbonate trimethylene glycol Chemical compound 0.000 title claims abstract description 12
- 239000000203 mixture Substances 0.000 title claims abstract description 9
- 239000002904 solvent Substances 0.000 claims abstract description 21
- 239000003456 ion exchange resin Substances 0.000 claims abstract description 9
- 229920003303 ion-exchange polymer Polymers 0.000 claims abstract description 9
- 230000002378 acidificating effect Effects 0.000 claims abstract description 8
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 29
- 239000003054 catalyst Substances 0.000 claims description 25
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 16
- 125000001424 substituent group Chemical group 0.000 claims description 16
- YBQPOMCDZYHDOD-UHFFFAOYSA-N C(C(C)O)O.C(O)(O)=O.C(C(C)O)O Chemical compound C(C(C)O)O.C(O)(O)=O.C(C(C)O)O YBQPOMCDZYHDOD-UHFFFAOYSA-N 0.000 claims description 15
- FOWDZVNRQHPXDO-UHFFFAOYSA-N propyl hydrogen carbonate Chemical compound CCCOC(O)=O FOWDZVNRQHPXDO-UHFFFAOYSA-N 0.000 claims description 15
- 125000004122 cyclic group Chemical group 0.000 claims 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 description 8
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 8
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 8
- 229920000642 polymer Polymers 0.000 claims description 7
- 239000000126 substance Substances 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 5
- 229920001577 copolymer Polymers 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims 2
- SELFXCFVPOJKBE-UHFFFAOYSA-N 2-(1-ethenoxypropan-2-yloxy)ethanesulfonic acid Chemical compound C=COCC(C)OCCS(O)(=O)=O SELFXCFVPOJKBE-UHFFFAOYSA-N 0.000 claims 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims 1
- ZWAQXZANTMWYAH-UHFFFAOYSA-N hept-6-enyl hydrogen sulfate Chemical compound O(CCCCCC=C)S(=O)(=O)O ZWAQXZANTMWYAH-UHFFFAOYSA-N 0.000 claims 1
- 238000005342 ion exchange Methods 0.000 claims 1
- 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
- 229920000557 Nafion® Polymers 0.000 description 27
- 238000006243 chemical reaction Methods 0.000 description 22
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 18
- 239000000463 material Substances 0.000 description 14
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Chemical group C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 7
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 7
- 229940035437 1,3-propanediol Drugs 0.000 description 7
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 7
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical group C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 238000005481 NMR spectroscopy Methods 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 239000000376 reactant Substances 0.000 description 5
- 238000001816 cooling Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 229920000515 polycarbonate Polymers 0.000 description 4
- 239000004417 polycarbonate Substances 0.000 description 4
- 238000000425 proton nuclear magnetic resonance spectrum Methods 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
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 238000004458 analytical method Methods 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
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 3
- VUPKGFBOKBGHFZ-UHFFFAOYSA-N dipropyl carbonate Chemical compound CCCOC(=O)OCCC VUPKGFBOKBGHFZ-UHFFFAOYSA-N 0.000 description 3
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 3
- ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical compound CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 description 3
- 239000011550 stock solution Substances 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 238000002306 biochemical method Methods 0.000 description 2
- 239000012620 biological material Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N n-butylhexane Natural products CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 1
- KNDAEDDIIQYRHY-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-3-(piperazin-1-ylmethyl)pyrazol-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C=1C(=NN(C=1)CC(=O)N1CC2=C(CC1)NN=N2)CN1CCNCC1 KNDAEDDIIQYRHY-UHFFFAOYSA-N 0.000 description 1
- DITDKJOHAAZUGD-UHFFFAOYSA-N 4-methyl-1,3-dioxolan-2-one;propane-1,2-diol Chemical compound CC(O)CO.CC1COC(=O)O1 DITDKJOHAAZUGD-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- RCIDUZQFFZBART-UHFFFAOYSA-N [He].[C] Chemical compound [He].[C] RCIDUZQFFZBART-UHFFFAOYSA-N 0.000 description 1
- NIXUOOJQLWGESL-UHFFFAOYSA-K [Ru](Cl)(Cl)Cl.[C] Chemical compound [Ru](Cl)(Cl)Cl.[C] NIXUOOJQLWGESL-UHFFFAOYSA-K 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000010538 cationic polymerization reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000009841 combustion method Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000012691 depolymerization reaction Methods 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
- 235000019439 ethyl acetate Nutrition 0.000 description 1
- OJCSPXHYDFONPU-UHFFFAOYSA-N etoac etoac Chemical compound CCOC(C)=O.CCOC(C)=O OJCSPXHYDFONPU-UHFFFAOYSA-N 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 229920000554 ionomer Polymers 0.000 description 1
- 150000002500 ions Chemical class 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
- 238000002156 mixing Methods 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- LLJLNFPEIFZYIW-UHFFFAOYSA-N propane-1,2-diol;prop-2-enoic acid Chemical compound CC(O)CO.CC(O)CO.OC(=O)C=C LLJLNFPEIFZYIW-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000003303 reheating Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000002076 thermal analysis method Methods 0.000 description 1
- 239000006200 vaporizer Substances 0.000 description 1
- 230000004580 weight loss Effects 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 (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US99169407P | 2007-11-30 | 2007-11-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TW200932781A true TW200932781A (en) | 2009-08-01 |
Family
ID=40351552
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW097146511A TW200932781A (en) | 2007-11-30 | 2008-11-28 | Compositions of and processes for producing a poly (trimethylene glycol carbonate trimethylene glycol ether) diol |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US20090143624A1 (https=) |
| EP (1) | EP2215143A1 (https=) |
| JP (1) | JP2011505469A (https=) |
| KR (1) | KR20100099713A (https=) |
| CN (1) | CN101878246A (https=) |
| AU (1) | AU2008329782A1 (https=) |
| CA (1) | CA2704028A1 (https=) |
| MX (1) | MX2010005760A (https=) |
| TW (1) | TW200932781A (https=) |
| WO (1) | WO2009070591A1 (https=) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BRPI0817142A2 (pt) * | 2007-11-30 | 2015-03-31 | Du Pont | "composição, processo para preparar um copolímero, elastrômero termoplástico, copolímero e produtos acabado" |
| 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 |
| 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 |
| KR101850950B1 (ko) | 2010-10-20 | 2018-04-20 | 신토고교 가부시키가이샤 | 전고체 전지를 구성하는 층 구조체의 제조 방법, 제조 장치 및 그 층 구조체를 구비한 전고체 전지 |
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) |
| AU2002333333A1 (en) * | 2001-08-17 | 2003-03-03 | Ucb, S.A. | Process for making a compound containing cyclic and linear carbonate groups |
| ES2380173T3 (es) * | 2007-11-30 | 2012-05-09 | E. I. Du Pont De Nemours And Company | Procedimiento para hacer un glicol de poli(carbonato de trimetileno) |
| 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 MX MX2010005760A patent/MX2010005760A/es unknown
- 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 AU AU2008329782A patent/AU2008329782A1/en not_active Abandoned
- 2008-11-25 CN CN2008801183110A patent/CN101878246A/zh active Pending
- 2008-11-25 WO PCT/US2008/084704 patent/WO2009070591A1/en not_active Ceased
- 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 |
|---|---|
| EP2215143A1 (en) | 2010-08-11 |
| MX2010005760A (es) | 2010-06-11 |
| CA2704028A1 (en) | 2009-06-04 |
| KR20100099713A (ko) | 2010-09-13 |
| CN101878246A (zh) | 2010-11-03 |
| US20090143624A1 (en) | 2009-06-04 |
| WO2009070591A1 (en) | 2009-06-04 |
| JP2011505469A (ja) | 2011-02-24 |
| AU2008329782A1 (en) | 2009-06-04 |
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