CA2704744A1 - Preparation of polytrimethylene ether glycol or copolymers thereof - Google Patents
Preparation of polytrimethylene ether glycol or copolymers thereof Download PDFInfo
- Publication number
- CA2704744A1 CA2704744A1 CA2704744A CA2704744A CA2704744A1 CA 2704744 A1 CA2704744 A1 CA 2704744A1 CA 2704744 A CA2704744 A CA 2704744A CA 2704744 A CA2704744 A CA 2704744A CA 2704744 A1 CA2704744 A1 CA 2704744A1
- Authority
- CA
- Canada
- Prior art keywords
- temperature
- reaction
- acid
- propanediol
- molecular weight
- 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.)
- Abandoned
Links
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 title claims abstract description 61
- -1 polytrimethylene Polymers 0.000 title claims abstract description 61
- 229920001577 copolymer Polymers 0.000 title claims abstract description 20
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 title claims description 71
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 title claims description 28
- 238000002360 preparation method Methods 0.000 title description 2
- 238000006243 chemical reaction Methods 0.000 claims abstract description 92
- 238000006068 polycondensation reaction Methods 0.000 claims abstract description 40
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 claims description 57
- 229920000166 polytrimethylene carbonate Polymers 0.000 claims description 57
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 claims description 55
- 239000003054 catalyst Substances 0.000 claims description 49
- 239000007795 chemical reaction product Substances 0.000 claims description 47
- 238000000034 method Methods 0.000 claims description 37
- 230000035484 reaction time Effects 0.000 claims description 36
- 150000002009 diols Chemical class 0.000 claims description 29
- 239000011541 reaction mixture Substances 0.000 claims description 28
- 241001550224 Apha Species 0.000 claims description 26
- 239000000376 reactant Substances 0.000 claims description 20
- KZWJWYFPLXRYIL-UHFFFAOYSA-N 1,1,2,2-tetrafluoroethanesulfonic acid Chemical compound OS(=O)(=O)C(F)(F)C(F)F KZWJWYFPLXRYIL-UHFFFAOYSA-N 0.000 claims description 19
- 239000000203 mixture Substances 0.000 claims description 16
- 238000006116 polymerization reaction Methods 0.000 claims description 13
- DMOBTBZPQXBGRE-UHFFFAOYSA-N 1,1,2,3,3,3-hexafluoropropane-1-sulfonic acid Chemical class OS(=O)(=O)C(F)(F)C(F)C(F)(F)F DMOBTBZPQXBGRE-UHFFFAOYSA-N 0.000 claims description 12
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 12
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 10
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 9
- 229920003303 ion-exchange polymer Polymers 0.000 claims description 9
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 6
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 claims description 6
- GHLKSLMMWAKNBM-UHFFFAOYSA-N dodecane-1,12-diol Chemical compound OCCCCCCCCCCCCO GHLKSLMMWAKNBM-UHFFFAOYSA-N 0.000 claims description 6
- JGTNAGYHADQMCM-UHFFFAOYSA-N perfluorobutanesulfonic acid Chemical compound OS(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F JGTNAGYHADQMCM-UHFFFAOYSA-N 0.000 claims description 6
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 claims description 6
- 239000000539 dimer Substances 0.000 claims description 5
- 239000000377 silicon dioxide Substances 0.000 claims description 5
- 239000013638 trimer Substances 0.000 claims description 5
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 4
- UQSQSQZYBQSBJZ-UHFFFAOYSA-N fluorosulfonic acid Chemical compound OS(F)(=O)=O UQSQSQZYBQSBJZ-UHFFFAOYSA-N 0.000 claims description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 4
- QWGRWMMWNDWRQN-UHFFFAOYSA-N 2-methylpropane-1,3-diol Chemical compound OCC(C)CO QWGRWMMWNDWRQN-UHFFFAOYSA-N 0.000 claims description 3
- 150000007513 acids Chemical class 0.000 claims description 3
- 239000012298 atmosphere Substances 0.000 claims description 3
- FOTKYAAJKYLFFN-UHFFFAOYSA-N decane-1,10-diol Chemical compound OCCCCCCCCCCO FOTKYAAJKYLFFN-UHFFFAOYSA-N 0.000 claims description 3
- SXCBDZAEHILGLM-UHFFFAOYSA-N heptane-1,7-diol Chemical compound OCCCCCCCO SXCBDZAEHILGLM-UHFFFAOYSA-N 0.000 claims description 3
- 238000005342 ion exchange Methods 0.000 claims description 3
- 239000003456 ion exchange resin Substances 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Chemical class 0.000 claims description 3
- 150000007522 mineralic acids Chemical class 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- 239000011973 solid acid Substances 0.000 claims description 3
- 150000003460 sulfonic acids Chemical class 0.000 claims description 3
- 239000010457 zeolite Substances 0.000 claims description 3
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 claims description 2
- 229940092714 benzenesulfonic acid Drugs 0.000 claims description 2
- NYENCOMLZDQKNH-UHFFFAOYSA-K bis(trifluoromethylsulfonyloxy)bismuthanyl trifluoromethanesulfonate Chemical compound [Bi+3].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F NYENCOMLZDQKNH-UHFFFAOYSA-K 0.000 claims description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 2
- WGJJZRVGLPOKQT-UHFFFAOYSA-K lanthanum(3+);trifluoromethanesulfonate Chemical compound [La+3].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F WGJJZRVGLPOKQT-UHFFFAOYSA-K 0.000 claims description 2
- 229940098779 methanesulfonic acid Drugs 0.000 claims description 2
- WYRSPTDNOIZOGA-UHFFFAOYSA-K neodymium(3+);trifluoromethanesulfonate Chemical compound [Nd+3].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F WYRSPTDNOIZOGA-UHFFFAOYSA-K 0.000 claims description 2
- QUADBKCRXGFGAX-UHFFFAOYSA-N octane-1,7-diol Chemical compound CC(O)CCCCCCO QUADBKCRXGFGAX-UHFFFAOYSA-N 0.000 claims description 2
- DHRLEVQXOMLTIM-UHFFFAOYSA-N phosphoric acid;trioxomolybdenum Chemical compound O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.OP(O)(O)=O DHRLEVQXOMLTIM-UHFFFAOYSA-N 0.000 claims description 2
- IYDGMDWEHDFVQI-UHFFFAOYSA-N phosphoric acid;trioxotungsten Chemical compound O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.OP(O)(O)=O IYDGMDWEHDFVQI-UHFFFAOYSA-N 0.000 claims description 2
- HZXJVDYQRYYYOR-UHFFFAOYSA-K scandium(iii) trifluoromethanesulfonate Chemical compound [Sc+3].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F HZXJVDYQRYYYOR-UHFFFAOYSA-K 0.000 claims description 2
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 claims description 2
- AHZJKOKFZJYCLG-UHFFFAOYSA-K trifluoromethanesulfonate;ytterbium(3+) Chemical compound [Yb+3].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F AHZJKOKFZJYCLG-UHFFFAOYSA-K 0.000 claims description 2
- JPJIEXKLJOWQQK-UHFFFAOYSA-K trifluoromethanesulfonate;yttrium(3+) Chemical compound [Y+3].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F JPJIEXKLJOWQQK-UHFFFAOYSA-K 0.000 claims description 2
- WJPWYVWFKYPSJS-UHFFFAOYSA-J trifluoromethanesulfonate;zirconium(4+) Chemical compound [Zr+4].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F WJPWYVWFKYPSJS-UHFFFAOYSA-J 0.000 claims description 2
- VMPVEPPRYRXYNP-UHFFFAOYSA-I antimony(5+);pentachloride Chemical compound Cl[Sb](Cl)(Cl)(Cl)Cl VMPVEPPRYRXYNP-UHFFFAOYSA-I 0.000 claims 1
- 239000003377 acid catalyst Substances 0.000 abstract description 9
- 238000004519 manufacturing process Methods 0.000 abstract description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 63
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 34
- 229920000642 polymer Polymers 0.000 description 25
- 229910001873 dinitrogen Inorganic materials 0.000 description 21
- 229910052757 nitrogen Inorganic materials 0.000 description 21
- 239000000047 product Substances 0.000 description 20
- 238000010438 heat treatment Methods 0.000 description 17
- 230000015572 biosynthetic process Effects 0.000 description 14
- 230000000052 comparative effect Effects 0.000 description 13
- 239000012456 homogeneous solution Substances 0.000 description 12
- 238000003786 synthesis reaction Methods 0.000 description 11
- 239000011521 glass Substances 0.000 description 10
- 239000000178 monomer Substances 0.000 description 9
- 238000011068 loading method Methods 0.000 description 8
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 6
- 239000007789 gas Substances 0.000 description 6
- 125000002843 carboxylic acid group Chemical group 0.000 description 5
- 239000006185 dispersion Substances 0.000 description 4
- 239000002638 heterogeneous catalyst Substances 0.000 description 4
- 239000002815 homogeneous catalyst Substances 0.000 description 4
- 210000003739 neck Anatomy 0.000 description 4
- 125000000542 sulfonic acid group Chemical group 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000000835 fiber Substances 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000004753 textile Substances 0.000 description 3
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- 239000004721 Polyphenylene oxide Substances 0.000 description 2
- 238000013019 agitation Methods 0.000 description 2
- 238000005341 cation exchange Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- 229920000570 polyether Polymers 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000003930 superacid Substances 0.000 description 2
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- YZUPZGFPHUVJKC-UHFFFAOYSA-N 1-bromo-2-methoxyethane Chemical compound COCCBr YZUPZGFPHUVJKC-UHFFFAOYSA-N 0.000 description 1
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical class OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 1
- 239000007848 Bronsted acid Substances 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- 229920000557 Nafion® Polymers 0.000 description 1
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 1
- CLBRCZAHAHECKY-UHFFFAOYSA-N [Co].[Pt] Chemical compound [Co].[Pt] CLBRCZAHAHECKY-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052787 antimony Inorganic materials 0.000 description 1
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000013626 chemical specie Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 125000005442 diisocyanate group Chemical group 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000011152 fibreglass Substances 0.000 description 1
- XUCNUKMRBVNAPB-UHFFFAOYSA-N fluoroethene Chemical compound FC=C XUCNUKMRBVNAPB-UHFFFAOYSA-N 0.000 description 1
- 239000013529 heat transfer fluid Substances 0.000 description 1
- HCDGVLDPFQMKDK-UHFFFAOYSA-N hexafluoropropylene Chemical group FC(F)=C(F)C(F)(F)F HCDGVLDPFQMKDK-UHFFFAOYSA-N 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000004816 latex Substances 0.000 description 1
- 229920000126 latex Polymers 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- QNDPUZFBWUBSNH-UHFFFAOYSA-I magic acid Chemical compound OS(F)(=O)=O.F[Sb](F)(F)(F)F QNDPUZFBWUBSNH-UHFFFAOYSA-I 0.000 description 1
- OHZZTXYKLXZFSZ-UHFFFAOYSA-I manganese(3+) 5,10,15-tris(1-methylpyridin-1-ium-4-yl)-20-(1-methylpyridin-4-ylidene)porphyrin-22-ide pentachloride Chemical compound [Cl-].[Cl-].[Cl-].[Cl-].[Cl-].[Mn+3].C1=CN(C)C=CC1=C1C(C=C2)=NC2=C(C=2C=C[N+](C)=CC=2)C([N-]2)=CC=C2C(C=2C=C[N+](C)=CC=2)=C(C=C2)N=C2C(C=2C=C[N+](C)=CC=2)=C2N=C1C=C2 OHZZTXYKLXZFSZ-UHFFFAOYSA-I 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- QLOAVXSYZAJECW-UHFFFAOYSA-N methane;molecular fluorine Chemical group C.FF QLOAVXSYZAJECW-UHFFFAOYSA-N 0.000 description 1
- OEIJHBUUFURJLI-UHFFFAOYSA-N octane-1,8-diol Chemical compound OCCCCCCCCO OEIJHBUUFURJLI-UHFFFAOYSA-N 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical compound CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 229910052761 rare earth metal Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- OBTWBSRJZRCYQV-UHFFFAOYSA-N sulfuryl difluoride Chemical group FS(F)(=O)=O OBTWBSRJZRCYQV-UHFFFAOYSA-N 0.000 description 1
- TXEYQDLBPFQVAA-UHFFFAOYSA-N tetrafluoromethane Chemical group FC(F)(F)F TXEYQDLBPFQVAA-UHFFFAOYSA-N 0.000 description 1
- 239000003017 thermal stabilizer Substances 0.000 description 1
- 229920002725 thermoplastic elastomer Polymers 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
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/34—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2205/00—Polymer mixtures characterised by other features
- C08L2205/05—Polymer mixtures characterised by other features containing polymer components which can react with one another
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyethers (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US98439807P | 2007-11-01 | 2007-11-01 | |
| US60/984,398 | 2007-11-01 | ||
| PCT/US2008/081997 WO2009059140A2 (en) | 2007-11-01 | 2008-10-31 | Preparation of polytrimethylene ether glycol |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2704744A1 true CA2704744A1 (en) | 2009-05-07 |
Family
ID=40565261
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2704744A Abandoned CA2704744A1 (en) | 2007-11-01 | 2008-10-31 | Preparation of polytrimethylene ether glycol or copolymers thereof |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US8148491B2 (enExample) |
| EP (1) | EP2215146A2 (enExample) |
| JP (1) | JP2011503261A (enExample) |
| KR (1) | KR20100105556A (enExample) |
| CN (1) | CN101842412A (enExample) |
| AU (1) | AU2008318469A1 (enExample) |
| BR (1) | BRPI0817160A2 (enExample) |
| CA (1) | CA2704744A1 (enExample) |
| MX (1) | MX2010004725A (enExample) |
| TW (1) | TW200938565A (enExample) |
| WO (1) | WO2009059140A2 (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101942084B (zh) * | 2010-09-25 | 2012-01-25 | 浙江大学 | 用三氟甲磺酸稀土金属化合物催化合成聚四氢呋喃的方法 |
| US8247526B2 (en) * | 2010-12-20 | 2012-08-21 | E I Du Pont De Nemours And Company | Process for the preparation of polyalkylene ether glycol |
| CN116144008A (zh) * | 2021-11-23 | 2023-05-23 | 中昊晨光化工研究院有限公司 | 一种稳定剂及其在制备含氟聚合物中的应用 |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2520733A (en) * | 1946-08-26 | 1950-08-29 | Shell Dev | Polymers of trimethylene glycol |
| US3282875A (en) * | 1964-07-22 | 1966-11-01 | Du Pont | Fluorocarbon vinyl ether polymers |
| US3326985A (en) * | 1964-12-29 | 1967-06-20 | Shell Oil Co | Polytrimethylene glycol |
| US3366610A (en) * | 1965-05-14 | 1968-01-30 | Du Pont | Perhalogenated epoxy olefin monomers and polymers |
| US4329435A (en) * | 1979-05-31 | 1982-05-11 | Asahi Kasei Kogyo Kabushiki Kaisha | Novel fluorinated copolymer with tridihydro fluorosulfonyl fluoride pendant groups and preparation thereof |
| US4358545A (en) * | 1980-06-11 | 1982-11-09 | The Dow Chemical Company | Sulfonic acid electrolytic cell having flourinated polymer membrane with hydration product less than 22,000 |
| US4330654A (en) * | 1980-06-11 | 1982-05-18 | The Dow Chemical Company | Novel polymers having acid functionality |
| US4433082A (en) * | 1981-05-01 | 1984-02-21 | E. I. Du Pont De Nemours And Company | Process for making liquid composition of perfluorinated ion exchange polymer, and product thereof |
| US4610762A (en) * | 1985-05-31 | 1986-09-09 | The Dow Chemical Company | Method for forming polymer films having bubble release surfaces |
| US5094995A (en) * | 1989-08-02 | 1992-03-10 | E. I. Du Pont De Nemours And Company | Supported perfluorinated ion-exchange polymers |
| US5824622A (en) * | 1994-01-12 | 1998-10-20 | E. I. Du Pont De Nemours And Company | Porous microcomposite of perfluorinated ion-exchange polymer and metal oxide, a network of silica, or a network of metal oxide and silica derived via a sol-gel process |
| WO2001044348A1 (en) * | 1999-12-17 | 2001-06-21 | E.I. Du Pont De Nemours And Company | Production of polytrimethylene ether glycol and copolymers thereof |
| EP1237835B1 (en) * | 1999-12-17 | 2006-09-20 | E.I. Du Pont De Nemours And Company | Continuous process for the preparation of polytrimethylene ether glycol |
| EP1940761B1 (en) * | 2005-09-22 | 2009-05-06 | E.I. Du Pont De Nemours And Company | Preparation of polytrimethylene ether glycol and copolymers thereof |
-
2008
- 2008-10-31 CN CN200880114161A patent/CN101842412A/zh active Pending
- 2008-10-31 WO PCT/US2008/081997 patent/WO2009059140A2/en not_active Ceased
- 2008-10-31 US US12/262,626 patent/US8148491B2/en not_active Expired - Fee Related
- 2008-10-31 EP EP08844960A patent/EP2215146A2/en not_active Withdrawn
- 2008-10-31 KR KR1020107011915A patent/KR20100105556A/ko not_active Withdrawn
- 2008-10-31 JP JP2010532280A patent/JP2011503261A/ja not_active Abandoned
- 2008-10-31 AU AU2008318469A patent/AU2008318469A1/en not_active Abandoned
- 2008-10-31 BR BRPI0817160 patent/BRPI0817160A2/pt not_active IP Right Cessation
- 2008-10-31 CA CA2704744A patent/CA2704744A1/en not_active Abandoned
- 2008-10-31 MX MX2010004725A patent/MX2010004725A/es unknown
- 2008-11-03 TW TW097142450A patent/TW200938565A/zh unknown
Also Published As
| Publication number | Publication date |
|---|---|
| KR20100105556A (ko) | 2010-09-29 |
| BRPI0817160A2 (pt) | 2015-03-31 |
| EP2215146A2 (en) | 2010-08-11 |
| JP2011503261A (ja) | 2011-01-27 |
| WO2009059140A3 (en) | 2009-06-18 |
| US8148491B2 (en) | 2012-04-03 |
| MX2010004725A (es) | 2010-05-20 |
| CN101842412A (zh) | 2010-09-22 |
| TW200938565A (en) | 2009-09-16 |
| AU2008318469A1 (en) | 2009-05-07 |
| US20090118465A1 (en) | 2009-05-07 |
| WO2009059140A2 (en) | 2009-05-07 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |
Effective date: 20131031 |