CA2472418A1 - Copolymers of tetrahydrofuran, ethylene oxide and an additional cyclic ether - Google Patents
Copolymers of tetrahydrofuran, ethylene oxide and an additional cyclic ether Download PDFInfo
- Publication number
- CA2472418A1 CA2472418A1 CA002472418A CA2472418A CA2472418A1 CA 2472418 A1 CA2472418 A1 CA 2472418A1 CA 002472418 A CA002472418 A CA 002472418A CA 2472418 A CA2472418 A CA 2472418A CA 2472418 A1 CA2472418 A1 CA 2472418A1
- Authority
- CA
- Canada
- Prior art keywords
- ethylene oxide
- tetrahydrofuran
- thf
- cyclic ether
- copolymer
- 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
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 title claims abstract description 110
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 title claims abstract description 79
- 229920001577 copolymer Polymers 0.000 title claims abstract description 37
- 150000004292 cyclic ethers Chemical class 0.000 title claims abstract description 31
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 title claims abstract description 12
- 230000000379 polymerizing effect Effects 0.000 claims abstract description 3
- 239000000470 constituent Substances 0.000 claims abstract 7
- 229920000642 polymer Polymers 0.000 claims description 42
- 239000004814 polyurethane Substances 0.000 claims description 22
- 229920002635 polyurethane Polymers 0.000 claims description 22
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 18
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 8
- UHHKSVZZTYJVEG-UHFFFAOYSA-N oxepane Chemical compound C1CCCOCC1 UHHKSVZZTYJVEG-UHFFFAOYSA-N 0.000 claims description 8
- 229920002334 Spandex Polymers 0.000 claims description 7
- 239000004759 spandex Substances 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical compound CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 claims description 5
- FZIIBDOXPQOKBP-UHFFFAOYSA-N 2-methyloxetane Chemical compound CC1CCO1 FZIIBDOXPQOKBP-UHFFFAOYSA-N 0.000 claims description 3
- RVGLUKRYMXEQAH-UHFFFAOYSA-N 3,3-dimethyloxetane Chemical compound CC1(C)COC1 RVGLUKRYMXEQAH-UHFFFAOYSA-N 0.000 claims description 3
- FVAHHPPJYLVIIC-UHFFFAOYSA-N 3,4-dimethyloxolane Chemical group CC1COCC1C FVAHHPPJYLVIIC-UHFFFAOYSA-N 0.000 claims description 3
- LJPCNSSTRWGCMZ-UHFFFAOYSA-N 3-methyloxolane Chemical compound CC1CCOC1 LJPCNSSTRWGCMZ-UHFFFAOYSA-N 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- FWICBZQTZDXXOL-UHFFFAOYSA-N oxecane Chemical compound C1CCCCOCCCC1 FWICBZQTZDXXOL-UHFFFAOYSA-N 0.000 claims description 3
- HZIVRQOIUMAXID-UHFFFAOYSA-N oxocane Chemical compound C1CCCOCCC1 HZIVRQOIUMAXID-UHFFFAOYSA-N 0.000 claims description 3
- YVQBOKCDPCUWSP-UHFFFAOYSA-N oxonane Chemical compound C1CCCCOCCC1 YVQBOKCDPCUWSP-UHFFFAOYSA-N 0.000 claims description 3
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 3
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 claims description 2
- 229920001228 polyisocyanate Polymers 0.000 claims description 2
- 239000005056 polyisocyanate Substances 0.000 claims description 2
- AIUUAKHKOQFCKF-UHFFFAOYSA-N 3-ethyloxolane Chemical compound CCC1CCOC1 AIUUAKHKOQFCKF-UHFFFAOYSA-N 0.000 claims 2
- 125000003566 oxetanyl group Chemical group 0.000 claims 1
- 230000007423 decrease Effects 0.000 abstract description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 26
- 239000000203 mixture Substances 0.000 description 20
- 239000007789 gas Substances 0.000 description 19
- 238000006116 polymerization reaction Methods 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 229910052757 nitrogen Inorganic materials 0.000 description 13
- 239000003054 catalyst Substances 0.000 description 12
- 238000007334 copolymerization reaction Methods 0.000 description 12
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 10
- 238000001914 filtration Methods 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 9
- -1 polytetramethylene Polymers 0.000 description 9
- 229920000557 Nafion® Polymers 0.000 description 8
- 239000000178 monomer Substances 0.000 description 8
- 238000005481 NMR spectroscopy Methods 0.000 description 7
- 239000002253 acid Substances 0.000 description 7
- UQSQSQZYBQSBJZ-UHFFFAOYSA-N fluorosulfonic acid Chemical class OS(F)(=O)=O UQSQSQZYBQSBJZ-UHFFFAOYSA-N 0.000 description 7
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 6
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 6
- 235000011089 carbon dioxide Nutrition 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 5
- 150000002334 glycols Chemical class 0.000 description 5
- 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 5
- 239000011949 solid catalyst Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 238000004448 titration Methods 0.000 description 5
- 229920001519 homopolymer Polymers 0.000 description 4
- 229920000909 polytetrahydrofuran Polymers 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 3
- 239000004970 Chain extender Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 125000005442 diisocyanate group Chemical group 0.000 description 3
- 230000002209 hydrophobic effect Effects 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 230000035945 sensitivity Effects 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 2
- 239000005909 Kieselgur Substances 0.000 description 2
- 239000002841 Lewis acid Substances 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 239000003377 acid catalyst Substances 0.000 description 2
- VHRGRCVQAFMJIZ-UHFFFAOYSA-N cadaverine Chemical compound NCCCCCN VHRGRCVQAFMJIZ-UHFFFAOYSA-N 0.000 description 2
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 2
- 239000000920 calcium hydroxide Substances 0.000 description 2
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- 150000004985 diamines Chemical class 0.000 description 2
- 150000005690 diesters Chemical class 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 238000005227 gel permeation chromatography Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 229920003303 ion-exchange polymer Polymers 0.000 description 2
- 238000011068 loading method Methods 0.000 description 2
- AVFBYUADVDVJQL-UHFFFAOYSA-N phosphoric acid;trioxotungsten;hydrate Chemical compound 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.O=[W](=O)=O.OP(O)(O)=O AVFBYUADVDVJQL-UHFFFAOYSA-N 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 239000002685 polymerization catalyst Substances 0.000 description 2
- 229920003226 polyurethane urea Polymers 0.000 description 2
- 238000011175 product filtration Methods 0.000 description 2
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 2
- 150000003460 sulfonic acids Chemical class 0.000 description 2
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 2
- 238000001291 vacuum drying Methods 0.000 description 2
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 1
- PZVANPGBOPAOIK-UHFFFAOYSA-N (1,3,3-trimethylcyclohexyl)methanamine Chemical compound CC1(C)CCCC(C)(CN)C1 PZVANPGBOPAOIK-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 1
- 229940035437 1,3-propanediol Drugs 0.000 description 1
- BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 description 1
- KMKROLUYWRLWCT-UHFFFAOYSA-N 2,2-dimethylbutane-1,3-diamine Chemical compound CC(N)C(C)(C)CN KMKROLUYWRLWCT-UHFFFAOYSA-N 0.000 description 1
- WUKHWLIEBSRTRH-UHFFFAOYSA-N 2-(2,2,3,3,4,4,5,5,5-nonafluoropentyl)oxirane Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)CC1CO1 WUKHWLIEBSRTRH-UHFFFAOYSA-N 0.000 description 1
- JZUHIOJYCPIVLQ-UHFFFAOYSA-N 2-methylpentane-1,5-diamine Chemical compound NCC(C)CCCN JZUHIOJYCPIVLQ-UHFFFAOYSA-N 0.000 description 1
- QTKDDPSHNLZGRO-UHFFFAOYSA-N 4-methylcyclohexane-1,3-diamine Chemical compound CC1CCC(N)CC1N QTKDDPSHNLZGRO-UHFFFAOYSA-N 0.000 description 1
- 239000007848 Bronsted acid Substances 0.000 description 1
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- FDLQZKYLHJJBHD-UHFFFAOYSA-N [3-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=CC(CN)=C1 FDLQZKYLHJJBHD-UHFFFAOYSA-N 0.000 description 1
- HGFORHZGWTZQPS-UHFFFAOYSA-N [4-[(2-isocyanatophenyl)methyl]phenyl] cyanate Chemical compound O=C=NC1=CC=CC=C1CC1=CC=C(OC#N)C=C1 HGFORHZGWTZQPS-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- RGTXVXDNHPWPHH-UHFFFAOYSA-N butane-1,3-diamine Chemical compound CC(N)CCN RGTXVXDNHPWPHH-UHFFFAOYSA-N 0.000 description 1
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- GEQHKFFSPGPGLN-UHFFFAOYSA-N cyclohexane-1,3-diamine Chemical compound NC1CCCC(N)C1 GEQHKFFSPGPGLN-UHFFFAOYSA-N 0.000 description 1
- VKIRRGRTJUUZHS-UHFFFAOYSA-N cyclohexane-1,4-diamine Chemical compound NC1CCC(N)CC1 VKIRRGRTJUUZHS-UHFFFAOYSA-N 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- KORSJDCBLAPZEQ-UHFFFAOYSA-N dicyclohexylmethane-4,4'-diisocyanate Chemical compound C1CC(N=C=O)CCC1CC1CCC(N=C=O)CC1 KORSJDCBLAPZEQ-UHFFFAOYSA-N 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 150000002009 diols Chemical group 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- WTSXICLFTPPDTL-UHFFFAOYSA-N pentane-1,3-diamine Chemical compound CCC(N)CCN WTSXICLFTPPDTL-UHFFFAOYSA-N 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- 229920003225 polyurethane elastomer Polymers 0.000 description 1
- 229920006306 polyurethane fiber Polymers 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 1
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000001577 simple distillation Methods 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 239000003930 superacid Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 150000007984 tetrahydrofuranes Chemical class 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- 239000010457 zeolite 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
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
- C08G18/4854—Polyethers containing oxyalkylene groups having four carbon atoms in the alkylene group
-
- 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
- C08G65/18—Oxetanes
-
- 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
- C08G65/22—Cyclic ethers having at least one atom other than carbon and hydrogen outside the ring
- C08G65/223—Cyclic ethers having at least one atom other than carbon and hydrogen outside the ring containing halogens
- C08G65/226—Cyclic ethers having at least one atom other than carbon and hydrogen outside the ring containing halogens containing fluorine
-
- D—TEXTILES; PAPER
- D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
- D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
- D01F6/00—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof
- D01F6/58—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from homopolycondensation products
- D01F6/70—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from homopolycondensation products from polyurethanes
-
- 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)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Polyethers (AREA)
- Artificial Filaments (AREA)
- Polyurethanes Or Polyureas (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US34738502P | 2002-01-10 | 2002-01-10 | |
| US60/347,385 | 2002-01-10 | ||
| PCT/US2003/001330 WO2003059989A1 (en) | 2002-01-10 | 2003-01-09 | Copolymers of tetrahydrofuran, ethylene oxide and an additional cyclic ether |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2472418A1 true CA2472418A1 (en) | 2003-07-24 |
Family
ID=23363486
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002472418A Abandoned CA2472418A1 (en) | 2002-01-10 | 2003-01-09 | Copolymers of tetrahydrofuran, ethylene oxide and an additional cyclic ether |
Country Status (13)
| Country | Link |
|---|---|
| US (2) | US6989432B2 (https=) |
| EP (1) | EP1463771B1 (https=) |
| JP (1) | JP4296095B2 (https=) |
| KR (1) | KR100943119B1 (https=) |
| CN (1) | CN1293120C (https=) |
| AT (1) | ATE370178T1 (https=) |
| AU (1) | AU2003235677A1 (https=) |
| BR (1) | BR0307153A (https=) |
| CA (1) | CA2472418A1 (https=) |
| DE (1) | DE60315592T2 (https=) |
| ES (1) | ES2291637T3 (https=) |
| TW (1) | TWI300078B (https=) |
| WO (1) | WO2003059989A1 (https=) |
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| US20020178118A1 (en) * | 2001-05-25 | 2002-11-28 | Hamilton Thomas E. | Transaction based packet switched data service on a wireless network |
| US6989432B2 (en) * | 2002-01-10 | 2006-01-24 | Invista North America S.A.R.L. | Copolymers of tetrahydrofuran, ethylene oxide and an additional cyclic ether |
| US20060014918A1 (en) * | 2003-05-09 | 2006-01-19 | Acushnet Company | Compositions for use in golf balls |
| CA2606080A1 (en) * | 2005-05-09 | 2006-11-16 | Invista Technologies S.A.R.L. | Spandex from poly (tetramethylene-co-ethyleneether) glycols having high ethyleneether content |
| US8765901B2 (en) | 2005-05-09 | 2014-07-01 | Invista North America S.ár.l. | Spandex compositions for high speed spinning |
| US20090029802A1 (en) * | 2005-09-14 | 2009-01-29 | Murali Rajagopalan | Polyurea and polyurethane compositions for golf equipment |
| WO2007061446A1 (en) * | 2005-11-22 | 2007-05-31 | Invista Technologies S.A.R.L. | Spandex from high molecular weight poly (tetramethylene-co-ethyleneether) glycols |
| US20070117949A1 (en) * | 2005-11-22 | 2007-05-24 | Palmer Charles F Jr | Spandex from poly(tetramethylene-co-ethyleneether) glycols having low ethyleneether content |
| CN101313002B (zh) * | 2005-11-22 | 2012-12-26 | 因维斯塔技术有限公司 | 获自与聚合二醇共混的聚(四亚甲基-共聚-亚乙基醚)二醇的弹力纤维 |
| US7893181B2 (en) * | 2006-07-11 | 2011-02-22 | Fina Technology, Inc. | Bimodal film resin and products made therefrom |
| CN102170917B (zh) * | 2008-08-06 | 2015-09-02 | 英威达技术有限公司 | 物品和制造弹性复合结构的方法 |
| ES2578632T3 (es) * | 2009-04-15 | 2016-07-28 | Invista Technologies S.À.R.L. | Mejora de la Miscibilidad de compuestos inmiscibles de otro modo |
| US8551192B2 (en) | 2009-04-15 | 2013-10-08 | Invista North America S.A.R.L. | Miscibility of otherwise immiscible compounds |
| WO2010120291A1 (en) * | 2009-04-15 | 2010-10-21 | Invista Technologies S.A R.L. | Copolyether glycol manufacturing process |
| JP5572694B2 (ja) * | 2009-04-15 | 2014-08-13 | インヴィスタ テクノロジーズ エスアエルエル | 改良されたコポリエーテルグリコールの製法 |
| US8167490B2 (en) | 2009-04-22 | 2012-05-01 | Reynolds Consumer Products Inc. | Multilayer stretchy drawstring |
| JP5654018B2 (ja) * | 2009-08-24 | 2015-01-14 | インヴィスタ テクノロジーズ エスアエルエル | 改善されたポリエーテルグリコールの製造法 |
| JP5986070B2 (ja) | 2010-04-29 | 2016-09-06 | ダウ グローバル テクノロジーズ エルエルシー | 混成ポリエステル−ポリエーテルポリオール |
| BR112013025054B1 (pt) | 2011-03-31 | 2020-03-17 | Dow Global Technologies Llc | Método para produzir um poliéter poliol de cadeia curta |
| US20140213677A1 (en) * | 2011-10-14 | 2014-07-31 | Dow Global Technologies Llc | Hybrid polyester-polyether polyols for improved demold expansion in polyurethane rigid foams |
| US20140323772A1 (en) * | 2013-04-25 | 2014-10-30 | Invista North America S.A R.L. | Polyether glycol manufacturing process |
| JP6957911B2 (ja) * | 2017-03-15 | 2021-11-02 | 三菱ケミカル株式会社 | ポリエーテルポリオールの製造方法 |
| JP7083825B2 (ja) * | 2017-05-30 | 2022-06-13 | 保土谷化学工業株式会社 | バイオポリエーテルポリオールの製造方法、バイオポリエーテルポリオール及びバイオポリウレタン樹脂 |
| CN110220986B (zh) * | 2019-05-27 | 2021-08-24 | 浙江巨化技术中心有限公司 | 一种全氟磺酸相对分子质量及分布的分析方法 |
| PL3770199T3 (pl) * | 2019-07-26 | 2025-03-24 | Henkel Ag & Co. Kgaa | Polieteropoliol o niskiej zawartości oligomerów cyklicznych |
| JP7539631B2 (ja) * | 2020-03-11 | 2024-08-26 | 保土谷化学工業株式会社 | 高透湿性ポリウレタン樹脂 |
| CN111848898B (zh) * | 2020-07-31 | 2021-12-07 | 浙江大学 | 一种含杂原子聚合物的制备方法 |
| US11859082B2 (en) * | 2020-12-31 | 2024-01-02 | Rohm And Haas Electronic Materials Llc | Polymers useful as surface leveling agents |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL110981C (https=) | 1957-03-08 | |||
| US3636132A (en) | 1969-07-19 | 1972-01-18 | Takeo Saegusa | Block copolymers of tetrahydrofuran and 3 3-bis(chloromethyl) oxetane |
| US3804812A (en) * | 1972-11-03 | 1974-04-16 | American Cyanamid Co | Process for preparing a segmented linear polyurethane polymer |
| US4163115A (en) | 1976-03-31 | 1979-07-31 | E. I. Du Pont De Nemours And Company | Preparation of esters of poly-(tetramethylene ether) glycol |
| US4153786A (en) | 1977-03-30 | 1979-05-08 | E. I. Du Pont De Nemours And Company | Method for preparing ester end-capped copolyether glycols |
| US4139567A (en) | 1977-03-30 | 1979-02-13 | E. I. Du Pont De Nemours And Company | Method for preparing copolyether glycols |
| US4211854A (en) | 1978-08-21 | 1980-07-08 | E. I. Du Pont De Nemours And Company | Block polymers of poly(tetramethylene oxide) and tetrahydrofuran/alkylene oxide copolymers |
| CA1216597A (en) * | 1983-05-23 | 1987-01-13 | Atsushi Aoshima | Process for producing polyetherglycol |
| US4658065A (en) | 1984-03-28 | 1987-04-14 | Asahi Kasei Kogyo Kabushiki Kaisha | Process for producing polyether polyol and a product |
| JP3717186B2 (ja) * | 1995-06-23 | 2005-11-16 | 旭化成せんい株式会社 | ポリウレタン弾性繊維及びその製造方法 |
| US5684179A (en) | 1995-12-14 | 1997-11-04 | E. I. Du Pont De Nemours And Company | Method for recovering diacetate esters of polytetramethylene ethers |
| TW343201B (en) | 1995-12-14 | 1998-10-21 | Du Pont | Improved method for manufacturing diacetate esters of polytetramethylene ethers |
| US5981686A (en) * | 1998-03-26 | 1999-11-09 | E. I. Du Pont De Nemours And Company | Spandex made with 1,3-diaminopentane |
| US6355846B1 (en) * | 2000-10-17 | 2002-03-12 | E. I. Du Pont De Nemours And Company | Narrowing of poly (tetramethylene ether) glycol |
| US6989432B2 (en) * | 2002-01-10 | 2006-01-24 | Invista North America S.A.R.L. | Copolymers of tetrahydrofuran, ethylene oxide and an additional cyclic ether |
| US20040211854A1 (en) * | 2003-04-23 | 2004-10-28 | Stephen Stamm | Buckle retainer for a tape cartridge |
-
2003
- 2003-01-08 US US10/338,396 patent/US6989432B2/en not_active Expired - Fee Related
- 2003-01-09 CN CNB038021587A patent/CN1293120C/zh not_active Expired - Fee Related
- 2003-01-09 JP JP2003560085A patent/JP4296095B2/ja not_active Expired - Fee Related
- 2003-01-09 KR KR1020047010660A patent/KR100943119B1/ko not_active Expired - Fee Related
- 2003-01-09 WO PCT/US2003/001330 patent/WO2003059989A1/en not_active Ceased
- 2003-01-09 EP EP03729686A patent/EP1463771B1/en not_active Expired - Lifetime
- 2003-01-09 BR BR0307153-7A patent/BR0307153A/pt not_active IP Right Cessation
- 2003-01-09 DE DE60315592T patent/DE60315592T2/de not_active Expired - Lifetime
- 2003-01-09 AU AU2003235677A patent/AU2003235677A1/en not_active Abandoned
- 2003-01-09 AT AT03729686T patent/ATE370178T1/de not_active IP Right Cessation
- 2003-01-09 CA CA002472418A patent/CA2472418A1/en not_active Abandoned
- 2003-01-09 ES ES03729686T patent/ES2291637T3/es not_active Expired - Lifetime
- 2003-01-10 TW TW092100501A patent/TWI300078B/zh not_active IP Right Cessation
-
2005
- 2005-12-02 US US11/292,456 patent/US20060084786A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| KR100943119B1 (ko) | 2010-02-18 |
| WO2003059989A1 (en) | 2003-07-24 |
| US6989432B2 (en) | 2006-01-24 |
| CN1615329A (zh) | 2005-05-11 |
| US20030166821A1 (en) | 2003-09-04 |
| ES2291637T3 (es) | 2008-03-01 |
| AU2003235677A1 (en) | 2003-07-30 |
| TW200307706A (en) | 2003-12-16 |
| JP4296095B2 (ja) | 2009-07-15 |
| ATE370178T1 (de) | 2007-09-15 |
| BR0307153A (pt) | 2004-12-07 |
| EP1463771B1 (en) | 2007-08-15 |
| EP1463771A1 (en) | 2004-10-06 |
| DE60315592T2 (de) | 2008-05-08 |
| KR20040105700A (ko) | 2004-12-16 |
| DE60315592D1 (de) | 2007-09-27 |
| JP2005532419A (ja) | 2005-10-27 |
| TWI300078B (en) | 2008-08-21 |
| CN1293120C (zh) | 2007-01-03 |
| US20060084786A1 (en) | 2006-04-20 |
| HK1078098A1 (en) | 2006-03-03 |
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