JP4901061B2 - オキシテトラメチレングリコール共重合体及びその製造方法 - Google Patents
オキシテトラメチレングリコール共重合体及びその製造方法 Download PDFInfo
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- JP4901061B2 JP4901061B2 JP2002556649A JP2002556649A JP4901061B2 JP 4901061 B2 JP4901061 B2 JP 4901061B2 JP 2002556649 A JP2002556649 A JP 2002556649A JP 2002556649 A JP2002556649 A JP 2002556649A JP 4901061 B2 JP4901061 B2 JP 4901061B2
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- Japan
- Prior art keywords
- molecular weight
- glycol copolymer
- reaction
- thf
- oxytetramethylene glycol
- 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 336
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 title claims abstract description 267
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 title claims abstract description 260
- 238000000034 method Methods 0.000 title claims abstract description 124
- 230000008569 process Effects 0.000 title description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims abstract description 591
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims abstract description 287
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 claims abstract description 220
- 238000007334 copolymerization reaction Methods 0.000 claims abstract description 146
- 150000002009 diols Chemical class 0.000 claims abstract description 133
- 239000011541 reaction mixture Substances 0.000 claims abstract description 105
- 238000009826 distribution Methods 0.000 claims abstract description 43
- 238000004519 manufacturing process Methods 0.000 claims abstract description 27
- 239000003054 catalyst Substances 0.000 claims description 170
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 146
- 238000006243 chemical reaction Methods 0.000 claims description 144
- 239000012071 phase Substances 0.000 claims description 138
- 239000012074 organic phase Substances 0.000 claims description 110
- 229930195734 saturated hydrocarbon Natural products 0.000 claims description 85
- 238000000746 purification Methods 0.000 claims description 54
- 238000006116 polymerization reaction Methods 0.000 claims description 52
- 239000011964 heteropoly acid Substances 0.000 claims description 46
- 229920000642 polymer Polymers 0.000 claims description 41
- 230000005484 gravity Effects 0.000 claims description 24
- 238000010533 azeotropic distillation Methods 0.000 claims description 13
- 239000006227 byproduct Substances 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 238000001944 continuous distillation Methods 0.000 claims description 7
- 239000003377 acid catalyst Substances 0.000 claims description 6
- 229940117969 neopentyl glycol Drugs 0.000 claims 10
- 238000004821 distillation Methods 0.000 description 93
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 61
- 239000000243 solution Substances 0.000 description 60
- 239000000203 mixture Substances 0.000 description 43
- 239000002994 raw material Substances 0.000 description 39
- 239000007788 liquid Substances 0.000 description 29
- 238000003756 stirring Methods 0.000 description 27
- 239000002253 acid Substances 0.000 description 26
- 230000009477 glass transition Effects 0.000 description 25
- -1 oxytetramethylene glycol Chemical compound 0.000 description 25
- 238000005227 gel permeation chromatography Methods 0.000 description 20
- 238000000199 molecular distillation Methods 0.000 description 20
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 18
- 239000000178 monomer Substances 0.000 description 18
- 230000008018 melting Effects 0.000 description 17
- 238000002844 melting Methods 0.000 description 17
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- 230000000694 effects Effects 0.000 description 16
- 239000000047 product Substances 0.000 description 15
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 14
- 239000003463 adsorbent Substances 0.000 description 14
- 230000000704 physical effect Effects 0.000 description 13
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
- 238000009835 boiling Methods 0.000 description 12
- 229920001519 homopolymer Polymers 0.000 description 12
- 230000005494 condensation Effects 0.000 description 11
- 239000000706 filtrate Substances 0.000 description 11
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 11
- 239000007787 solid Substances 0.000 description 11
- 229910052721 tungsten Inorganic materials 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 238000004458 analytical method Methods 0.000 description 10
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- 229920006158 high molecular weight polymer Polymers 0.000 description 10
- 239000007791 liquid phase Substances 0.000 description 10
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- CMPGARWFYBADJI-UHFFFAOYSA-L tungstic acid Chemical compound O[W](O)(=O)=O CMPGARWFYBADJI-UHFFFAOYSA-L 0.000 description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
- 235000002597 Solanum melongena Nutrition 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 9
- 238000004817 gas chromatography Methods 0.000 description 8
- 150000007522 mineralic acids Chemical class 0.000 description 8
- VLAPMBHFAWRUQP-UHFFFAOYSA-L molybdic acid Chemical compound O[Mo](O)(=O)=O VLAPMBHFAWRUQP-UHFFFAOYSA-L 0.000 description 8
- 238000011282 treatment Methods 0.000 description 8
- 239000010937 tungsten Substances 0.000 description 8
- 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
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 7
- 210000004177 elastic tissue Anatomy 0.000 description 7
- 238000005194 fractionation Methods 0.000 description 7
- 239000001301 oxygen Substances 0.000 description 7
- 229910052760 oxygen Inorganic materials 0.000 description 7
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 7
- 239000002244 precipitate Substances 0.000 description 7
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 7
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 229910052785 arsenic Inorganic materials 0.000 description 6
- 239000012298 atmosphere Substances 0.000 description 6
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 6
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 6
- 239000000920 calcium hydroxide Substances 0.000 description 6
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 6
- 239000012295 chemical reaction liquid Substances 0.000 description 6
- 239000003480 eluent Substances 0.000 description 6
- 238000002347 injection Methods 0.000 description 6
- 239000007924 injection Substances 0.000 description 6
- 238000010552 living cationic polymerization reaction Methods 0.000 description 6
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 6
- 238000005191 phase separation Methods 0.000 description 6
- 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
- 238000000926 separation method Methods 0.000 description 6
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 5
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 5
- 230000008859 change Effects 0.000 description 5
- 238000000354 decomposition reaction Methods 0.000 description 5
- 230000007423 decrease Effects 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 238000003860 storage Methods 0.000 description 5
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 4
- LAIUFBWHERIJIH-UHFFFAOYSA-N 3-Methylheptane Chemical compound CCCCC(C)CC LAIUFBWHERIJIH-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 241001550224 Apha Species 0.000 description 4
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 description 4
- 238000011088 calibration curve Methods 0.000 description 4
- 239000010941 cobalt Substances 0.000 description 4
- 229910017052 cobalt Inorganic materials 0.000 description 4
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 4
- DMEGYFMYUHOHGS-UHFFFAOYSA-N cycloheptane Chemical compound C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 4
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 4
- 238000003795 desorption Methods 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 150000002430 hydrocarbons Chemical group 0.000 description 4
- 230000014759 maintenance of location Effects 0.000 description 4
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 4
- GDOPTJXRTPNYNR-UHFFFAOYSA-N methylcyclopentane Chemical compound CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 description 4
- 239000011259 mixed solution Substances 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 4
- 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 description 4
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- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
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- 229910052736 halogen Inorganic materials 0.000 description 3
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- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
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- 229910052710 silicon Inorganic materials 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- UNVGBIALRHLALK-UHFFFAOYSA-N 1,5-Hexanediol Chemical compound CC(O)CCCCO UNVGBIALRHLALK-UHFFFAOYSA-N 0.000 description 2
- MWCBGWLCXSUTHK-UHFFFAOYSA-N 2-methylbutane-1,4-diol Chemical compound OCC(C)CCO MWCBGWLCXSUTHK-UHFFFAOYSA-N 0.000 description 2
- LJPCNSSTRWGCMZ-UHFFFAOYSA-N 3-methyloxolane Chemical compound CC1CCOC1 LJPCNSSTRWGCMZ-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- 229910052684 Cerium Inorganic materials 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
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- 125000004435 hydrogen atom Chemical group [H]* 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
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- OEIJHBUUFURJLI-UHFFFAOYSA-N octane-1,8-diol Chemical compound OCCCCCCCCO OEIJHBUUFURJLI-UHFFFAOYSA-N 0.000 description 1
- 238000012643 polycondensation polymerization Methods 0.000 description 1
- 229920006254 polymer film Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920005749 polyurethane resin Polymers 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000005086 pumping Methods 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 238000004064 recycling 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
- 239000000126 substance Substances 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 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)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2002556649A JP4901061B2 (ja) | 2001-01-11 | 2001-04-16 | オキシテトラメチレングリコール共重合体及びその製造方法 |
Applications Claiming Priority (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2001003899 | 2001-01-11 | ||
| JP2001003899 | 2001-01-11 | ||
| JP2001003810 | 2001-01-11 | ||
| JP2001003810 | 2001-01-11 | ||
| PCT/JP2001/003230 WO2002055586A1 (fr) | 2001-01-11 | 2001-04-16 | Copolymere d'oxytetramethylene glycol et son procede de production |
| JP2002556649A JP4901061B2 (ja) | 2001-01-11 | 2001-04-16 | オキシテトラメチレングリコール共重合体及びその製造方法 |
Publications (2)
| Publication Number | Publication Date |
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| JPWO2002055586A1 JPWO2002055586A1 (ja) | 2004-05-13 |
| JP4901061B2 true JP4901061B2 (ja) | 2012-03-21 |
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| JP2002556649A Expired - Lifetime JP4901061B2 (ja) | 2001-01-11 | 2001-04-16 | オキシテトラメチレングリコール共重合体及びその製造方法 |
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| EP (1) | EP1361243B1 (enExample) |
| JP (1) | JP4901061B2 (enExample) |
| KR (1) | KR100564874B1 (enExample) |
| CN (1) | CN1272362C (enExample) |
| AT (1) | ATE489418T1 (enExample) |
| CA (1) | CA2433731C (enExample) |
| DE (1) | DE60143547D1 (enExample) |
| TW (1) | TWI296632B (enExample) |
| WO (1) | WO2002055586A1 (enExample) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| JPH09291147A (ja) * | 1996-04-24 | 1997-11-11 | Asahi Chem Ind Co Ltd | ポリエーテルポリオールの精製法、及び該ポリエーテルポリオール中のジオールの回収法 |
| JPH1025340A (ja) * | 1996-04-10 | 1998-01-27 | Asahi Chem Ind Co Ltd | ポリエーテルジオールの製造方法 |
| 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 |
| JPH1087811A (ja) * | 1996-09-20 | 1998-04-07 | Asahi Chem Ind Co Ltd | 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 |
Family Cites Families (7)
| 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 |
| 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 |
| 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
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Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| JPH1025340A (ja) * | 1996-04-10 | 1998-01-27 | Asahi Chem Ind Co Ltd | ポリエーテルジオールの製造方法 |
| JPH09291147A (ja) * | 1996-04-24 | 1997-11-11 | Asahi Chem Ind Co Ltd | ポリエーテルポリオールの精製法、及び該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 |
| JPH1087811A (ja) * | 1996-09-20 | 1998-04-07 | Asahi Chem Ind Co Ltd | 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 |
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 |
| US20070173631A1 (en) | 2007-07-26 |
| TWI296632B (enExample) | 2008-05-11 |
| DE60143547D1 (de) | 2011-01-05 |
| KR100564874B1 (ko) | 2006-03-30 |
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