CA2755923A1 - Membranes polymeres de polybenzoxazole et de polybenzothiazole reticules a haut rendement - Google Patents
Membranes polymeres de polybenzoxazole et de polybenzothiazole reticules a haut rendement Download PDFInfo
- Publication number
- CA2755923A1 CA2755923A1 CA2755923A CA2755923A CA2755923A1 CA 2755923 A1 CA2755923 A1 CA 2755923A1 CA 2755923 A CA2755923 A CA 2755923A CA 2755923 A CA2755923 A CA 2755923A CA 2755923 A1 CA2755923 A1 CA 2755923A1
- Authority
- CA
- Canada
- Prior art keywords
- membranes
- cross
- polymer
- membrane
- poly
- 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
- 229920005597 polymer membrane Polymers 0.000 title claims abstract description 153
- 229920002577 polybenzoxazole Polymers 0.000 title claims abstract description 127
- 239000012528 membrane Substances 0.000 claims abstract description 205
- 239000007789 gas Substances 0.000 claims abstract description 95
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 62
- 229920000642 polymer Polymers 0.000 claims abstract description 61
- 239000004642 Polyimide Substances 0.000 claims abstract description 59
- 229920001721 polyimide Polymers 0.000 claims abstract description 59
- 238000000034 method Methods 0.000 claims abstract description 46
- 239000007788 liquid Substances 0.000 claims abstract description 34
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 31
- 230000005855 radiation Effects 0.000 claims abstract description 27
- 125000000524 functional group Chemical group 0.000 claims abstract description 24
- 238000010438 heat treatment Methods 0.000 claims abstract description 21
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 16
- 150000003949 imides Chemical class 0.000 claims abstract description 16
- 238000004132 cross linking Methods 0.000 claims abstract description 15
- 230000002194 synthesizing effect Effects 0.000 claims abstract description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 105
- 239000000203 mixture Substances 0.000 claims description 43
- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 40
- 230000035699 permeability Effects 0.000 claims description 36
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 26
- 230000008569 process Effects 0.000 claims description 23
- 239000003345 natural gas Substances 0.000 claims description 21
- -1 polysiloxane Polymers 0.000 claims description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 15
- 238000006243 chemical reaction Methods 0.000 claims description 13
- 239000001569 carbon dioxide Substances 0.000 claims description 11
- 239000012188 paraffin wax Substances 0.000 claims description 10
- 239000000463 material Substances 0.000 claims description 8
- 239000012466 permeate Substances 0.000 claims description 8
- 229920001296 polysiloxane Polymers 0.000 claims description 8
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims description 7
- 150000001336 alkenes Chemical class 0.000 claims description 7
- 229910000037 hydrogen sulfide Inorganic materials 0.000 claims description 7
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
- 239000001301 oxygen Substances 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 239000004593 Epoxy Substances 0.000 claims description 4
- 239000004811 fluoropolymer Substances 0.000 claims description 4
- 239000001307 helium Substances 0.000 claims description 4
- 229910052734 helium Inorganic materials 0.000 claims description 4
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 claims description 4
- 229920002379 silicone rubber Polymers 0.000 claims description 4
- 239000004945 silicone rubber Substances 0.000 claims description 4
- KZTYYGOKRVBIMI-UHFFFAOYSA-N S-phenyl benzenesulfonothioate Natural products C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 claims description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 claims description 2
- 239000011248 coating agent Substances 0.000 claims description 2
- 238000000576 coating method Methods 0.000 claims description 2
- 238000010382 chemical cross-linking Methods 0.000 claims 1
- 238000000926 separation method Methods 0.000 abstract description 63
- 229930195733 hydrocarbon Natural products 0.000 description 23
- 150000002430 hydrocarbons Chemical class 0.000 description 23
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 21
- 239000004215 Carbon black (E152) Substances 0.000 description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 15
- 239000002808 molecular sieve Substances 0.000 description 15
- 238000002360 preparation method Methods 0.000 description 15
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 15
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 14
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 14
- 238000012360 testing method Methods 0.000 description 14
- 239000002904 solvent Substances 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 229920002301 cellulose acetate Polymers 0.000 description 12
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 12
- 238000011084 recovery Methods 0.000 description 12
- 230000015572 biosynthetic process Effects 0.000 description 11
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 10
- 125000003118 aryl group Chemical group 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- 239000001294 propane Substances 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 10
- 239000000126 substance Substances 0.000 description 9
- 239000011521 glass Substances 0.000 description 8
- 101100243025 Arabidopsis thaliana PCO2 gene Proteins 0.000 description 7
- 230000004907 flux Effects 0.000 description 7
- 101100378191 Caenorhabditis elegans aco-2 gene Proteins 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 6
- 229910052753 mercury Inorganic materials 0.000 description 6
- 238000005373 pervaporation Methods 0.000 description 6
- 239000002861 polymer material Substances 0.000 description 6
- YYAVXASAKUOZJJ-UHFFFAOYSA-N 4-(4-butylcyclohexyl)benzonitrile Chemical compound C1CC(CCCC)CCC1C1=CC=C(C#N)C=C1 YYAVXASAKUOZJJ-UHFFFAOYSA-N 0.000 description 5
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 5
- 229910052786 argon Inorganic materials 0.000 description 5
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 5
- 238000005266 casting Methods 0.000 description 5
- 230000007423 decrease Effects 0.000 description 5
- 238000009792 diffusion process Methods 0.000 description 5
- 230000001965 increasing effect Effects 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 150000002894 organic compounds Chemical class 0.000 description 5
- 229920005575 poly(amic acid) Polymers 0.000 description 5
- 201000003034 pontocerebellar hypoplasia type 4 Diseases 0.000 description 5
- 238000004088 simulation Methods 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000000356 contaminant Substances 0.000 description 4
- 239000000835 fiber Substances 0.000 description 4
- 239000003502 gasoline Substances 0.000 description 4
- 239000012510 hollow fiber Substances 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 238000007654 immersion Methods 0.000 description 4
- 239000010453 quartz Substances 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 230000008961 swelling Effects 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- QQGYZOYWNCKGEK-UHFFFAOYSA-N 5-[(1,3-dioxo-2-benzofuran-5-yl)oxy]-2-benzofuran-1,3-dione Chemical compound C1=C2C(=O)OC(=O)C2=CC(OC=2C=C3C(=O)OC(C3=CC=2)=O)=C1 QQGYZOYWNCKGEK-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000003463 adsorbent Substances 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 239000012024 dehydrating agents Substances 0.000 description 3
- 238000010612 desalination reaction Methods 0.000 description 3
- 238000006477 desulfuration reaction Methods 0.000 description 3
- 230000023556 desulfurization Effects 0.000 description 3
- 239000002283 diesel fuel Substances 0.000 description 3
- 229920002521 macromolecule Polymers 0.000 description 3
- 230000007246 mechanism Effects 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 239000002798 polar solvent Substances 0.000 description 3
- 229920002480 polybenzimidazole Polymers 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 230000008707 rearrangement Effects 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- 230000002829 reductive effect Effects 0.000 description 3
- 238000001223 reverse osmosis Methods 0.000 description 3
- 230000002459 sustained effect Effects 0.000 description 3
- 239000010409 thin film Substances 0.000 description 3
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 2
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 2
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 239000002131 composite material Substances 0.000 description 2
- 230000006835 compression Effects 0.000 description 2
- 238000007906 compression Methods 0.000 description 2
- 230000018044 dehydration Effects 0.000 description 2
- 238000006297 dehydration reaction Methods 0.000 description 2
- 239000002019 doping agent Substances 0.000 description 2
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- 238000000855 fermentation Methods 0.000 description 2
- 230000004151 fermentation Effects 0.000 description 2
- 238000004231 fluid catalytic cracking Methods 0.000 description 2
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 239000002609 medium Substances 0.000 description 2
- 229910052751 metal Chemical class 0.000 description 2
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- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 239000012855 volatile organic compound Substances 0.000 description 2
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- MSTZGVRUOMBULC-UHFFFAOYSA-N 2-amino-4-[2-(3-amino-4-hydroxyphenyl)-1,1,1,3,3,3-hexafluoropropan-2-yl]phenol Chemical compound C1=C(O)C(N)=CC(C(C=2C=C(N)C(O)=CC=2)(C(F)(F)F)C(F)(F)F)=C1 MSTZGVRUOMBULC-UHFFFAOYSA-N 0.000 description 1
- USFQPQJCAAGKCS-UHFFFAOYSA-N 3-ethoxyhexane Chemical compound CCCC(CC)OCC USFQPQJCAAGKCS-UHFFFAOYSA-N 0.000 description 1
- VQVIHDPBMFABCQ-UHFFFAOYSA-N 5-(1,3-dioxo-2-benzofuran-5-carbonyl)-2-benzofuran-1,3-dione Chemical compound C1=C2C(=O)OC(=O)C2=CC(C(C=2C=C3C(=O)OC(=O)C3=CC=2)=O)=C1 VQVIHDPBMFABCQ-UHFFFAOYSA-N 0.000 description 1
- 101100007418 Caenorhabditis elegans cox-5A gene Proteins 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- MHABMANUFPZXEB-UHFFFAOYSA-N O-demethyl-aloesaponarin I Natural products O=C1C2=CC=CC(O)=C2C(=O)C2=C1C=C(O)C(C(O)=O)=C2C MHABMANUFPZXEB-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 1
- FOIXSVOLVBLSDH-UHFFFAOYSA-N Silver ion Chemical compound [Ag+] FOIXSVOLVBLSDH-UHFFFAOYSA-N 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical group ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- NVJHHSJKESILSZ-UHFFFAOYSA-N [Co].N1C(C=C2N=C(C=C3NC(=C4)C=C3)C=C2)=CC=C1C=C1C=CC4=N1 Chemical class [Co].N1C(C=C2N=C(C=C3NC(=C4)C=C3)C=C2)=CC=C1C=C1C=CC4=N1 NVJHHSJKESILSZ-UHFFFAOYSA-N 0.000 description 1
- CDXSJGDDABYYJV-UHFFFAOYSA-N acetic acid;ethanol Chemical compound CCO.CC(O)=O CDXSJGDDABYYJV-UHFFFAOYSA-N 0.000 description 1
- OKMHHBICYZAXBE-UHFFFAOYSA-N acetic acid;ethanol;ethyl acetate Chemical compound CCO.CC(O)=O.CCOC(C)=O OKMHHBICYZAXBE-UHFFFAOYSA-N 0.000 description 1
- 238000007605 air drying Methods 0.000 description 1
- 238000004887 air purification Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 230000003466 anti-cipated effect Effects 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- RPRPDTXKGSIXMD-UHFFFAOYSA-N butyl hexanoate Chemical compound CCCCCC(=O)OCCCC RPRPDTXKGSIXMD-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- UBAZGMLMVVQSCD-UHFFFAOYSA-N carbon dioxide;molecular oxygen Chemical compound O=O.O=C=O UBAZGMLMVVQSCD-UHFFFAOYSA-N 0.000 description 1
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- 238000006555 catalytic reaction Methods 0.000 description 1
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- 229910010293 ceramic material Inorganic materials 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- UXTMROKLAAOEQO-UHFFFAOYSA-N chloroform;ethanol Chemical compound CCO.ClC(Cl)Cl UXTMROKLAAOEQO-UHFFFAOYSA-N 0.000 description 1
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 1
- 229920000891 common polymer Polymers 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
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- 238000006356 dehydrogenation reaction Methods 0.000 description 1
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- 238000001514 detection method Methods 0.000 description 1
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- 150000004985 diamines Chemical class 0.000 description 1
- 125000006159 dianhydride group Chemical group 0.000 description 1
- 150000002012 dioxanes Chemical class 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
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- PSLIMVZEAPALCD-UHFFFAOYSA-N ethanol;ethoxyethane Chemical compound CCO.CCOCC PSLIMVZEAPALCD-UHFFFAOYSA-N 0.000 description 1
- LJQKCYFTNDAAPC-UHFFFAOYSA-N ethanol;ethyl acetate Chemical compound CCO.CCOC(C)=O LJQKCYFTNDAAPC-UHFFFAOYSA-N 0.000 description 1
- ONANCCRCSFDCRE-UHFFFAOYSA-N ethanol;methanol;propan-2-ol Chemical compound OC.CCO.CC(C)O ONANCCRCSFDCRE-UHFFFAOYSA-N 0.000 description 1
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- 239000003208 petroleum Substances 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
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- 238000006068 polycondensation reaction Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- AIISZVRFZVBASR-UHFFFAOYSA-N propan-1-ol;propyl acetate Chemical compound CCCO.CCCOC(C)=O AIISZVRFZVBASR-UHFFFAOYSA-N 0.000 description 1
- SAALQYKUFCIMHR-UHFFFAOYSA-N propan-2-ol;2-propan-2-yloxypropane Chemical compound CC(C)O.CC(C)OC(C)C SAALQYKUFCIMHR-UHFFFAOYSA-N 0.000 description 1
- AAZYNPCMLRQUHI-UHFFFAOYSA-N propan-2-one;2-propan-2-yloxypropane Chemical compound CC(C)=O.CC(C)OC(C)C AAZYNPCMLRQUHI-UHFFFAOYSA-N 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 238000011160 research Methods 0.000 description 1
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- 230000000717 retained effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
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- 238000001179 sorption measurement Methods 0.000 description 1
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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
- C08G75/00—Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule
- C08G75/32—Polythiazoles; Polythiadiazoles
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
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- B01D67/0081—After-treatment of organic or inorganic membranes
- B01D67/0083—Thermal after-treatment
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- B01D71/06—Organic material
- B01D71/66—Polymers having sulfur in the main chain, with or without nitrogen, oxygen or carbon only
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/1042—Copolyimides derived from at least two different tetracarboxylic compounds or two different diamino compounds
-
- 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
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/22—Polybenzoxazoles
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- C08J5/20—Manufacture of shaped structures of ion-exchange resins
- C08J5/22—Films, membranes or diaphragms
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
- C08J7/08—Heat treatment
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L79/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen or carbon only, not provided for in groups C08L61/00 - C08L77/00
- C08L79/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
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- B—PERFORMING OPERATIONS; TRANSPORTING
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- B01D—SEPARATION
- B01D2323/00—Details relating to membrane preparation
- B01D2323/30—Cross-linking
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D2323/00—Details relating to membrane preparation
- B01D2323/34—Use of radiation
- B01D2323/345—UV-treatment
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2379/00—Characterised by the use of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen, or carbon only, not provided for in groups C08J2361/00 - C08J2377/00
- C08J2379/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
-
- 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
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- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
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- Manufacturing & Machinery (AREA)
- Thermal Sciences (AREA)
- Inorganic Chemistry (AREA)
- Plasma & Fusion (AREA)
- Materials Engineering (AREA)
- Separation Using Semi-Permeable Membranes (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US12/412,629 US8127936B2 (en) | 2009-03-27 | 2009-03-27 | High performance cross-linked polybenzoxazole and polybenzothiazole polymer membranes |
| US12/412,633 US8127937B2 (en) | 2009-03-27 | 2009-03-27 | High performance cross-linked polybenzoxazole and polybenzothiazole polymer membranes |
| US12/412,629 | 2009-03-27 | ||
| US12/412,633 | 2009-03-27 | ||
| PCT/US2010/024855 WO2010110975A2 (fr) | 2009-03-27 | 2010-02-22 | Membranes polymères de polybenzoxazole et de polybenzothiazole réticulés à haut rendement |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2755923A1 true CA2755923A1 (fr) | 2010-09-30 |
Family
ID=42781743
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2755923A Abandoned CA2755923A1 (fr) | 2009-03-27 | 2010-02-22 | Membranes polymeres de polybenzoxazole et de polybenzothiazole reticules a haut rendement |
Country Status (9)
| Country | Link |
|---|---|
| EP (1) | EP2411130A4 (fr) |
| JP (1) | JP5607721B2 (fr) |
| KR (1) | KR101392124B1 (fr) |
| CN (1) | CN102448593A (fr) |
| AU (1) | AU2010229241B2 (fr) |
| BR (1) | BRPI1013695A2 (fr) |
| CA (1) | CA2755923A1 (fr) |
| MY (1) | MY157509A (fr) |
| WO (1) | WO2010110975A2 (fr) |
Families Citing this family (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7810652B2 (en) * | 2009-09-25 | 2010-10-12 | Uop Llc | Method to improve the selectivity of polybenzoxazole membranes |
| JP5747730B2 (ja) * | 2010-08-11 | 2015-07-15 | 宇部興産株式会社 | ポリイミドガス分離膜、及びガス分離方法 |
| US8614288B2 (en) * | 2011-06-17 | 2013-12-24 | Uop Llc | Polyimide gas separation membranes |
| JP5749608B2 (ja) * | 2011-09-02 | 2015-07-15 | 株式会社ダイセル | 相分離構造体及び有機半導体 |
| CN102560894A (zh) * | 2011-11-17 | 2012-07-11 | 江西先材纳米纤维科技有限公司 | 聚苯并二噁唑纳米纤维非织造布的制备方法及其应用 |
| US9321017B2 (en) | 2012-01-24 | 2016-04-26 | Nagoya Industrial Science Research Institute | Gas-separation membrane |
| CN102728237A (zh) * | 2012-06-20 | 2012-10-17 | 中国科学技术大学 | 均相阴离子交换膜及其制备方法 |
| JP6037804B2 (ja) * | 2012-12-03 | 2016-12-07 | 富士フイルム株式会社 | ガス分離膜 |
| JP6388125B2 (ja) * | 2013-01-16 | 2018-09-12 | 日産化学株式会社 | ディスプレイ基板用樹脂薄膜の製造方法及びディスプレイ基板用樹脂薄膜形成用組成物 |
| US20140255636A1 (en) * | 2013-03-06 | 2014-09-11 | Saudi Basic Industries Corporation | Polymeric Membranes |
| US9440197B2 (en) | 2013-07-01 | 2016-09-13 | ICUF-HYU (Industry-University Cooperation Foundation Hanyang University) | Crosslinked thermally rearranged poly(benzoxazole-co-imide), gas separation membranes comprising the same and preparation method thereof |
| KR101466918B1 (ko) | 2013-07-01 | 2014-12-04 | 한양대학교 산학협력단 | 가교구조를 갖는 열전환 폴리(벤즈옥사졸-이미드) 공중합체를 포함하는 배연가스 분리용 막 및 그 제조방법 |
| US9211508B2 (en) * | 2013-09-27 | 2015-12-15 | Uop Llc | Polybenzoxazole membranes from self-cross-linkable aromatic polyimide membranes |
| AU2014324439B2 (en) * | 2013-09-30 | 2017-10-26 | Air Liquide Advanced Technologies U.S., Llc | Asymmetric modified carbon molecular sieve hollow fiber membranes having improved permeance |
| WO2015072694A1 (fr) * | 2013-11-15 | 2015-05-21 | 한양대학교 산학협력단 | Membrane de séparation de gaz de carneau comprenant un copolymère poly(benzoxazole-imide) thermiquement réarrangé ayant une structure réticulée, et son procédé de préparation |
| KR101599898B1 (ko) | 2013-11-15 | 2016-03-04 | 한양대학교 산학협력단 | 기체분리용 가교구조를 갖는 열전환 폴리(벤즈옥사졸-이미드) 막의 제조방법 및 그에 의하여 제조된 기체분리막 |
| US10035109B2 (en) | 2013-11-15 | 2018-07-31 | Iucf-Hyu (Industry-University Cooperation Foundation Hanyang University) | Crosslinked, thermally rearranged poly(benzoxazole-co-imide), gas separation membranes comprising the same and preparation method thereof |
| WO2015095044A1 (fr) | 2013-12-16 | 2015-06-25 | Sabic Global Technologies B.V. | Membranes polymères traitées à matrice mixte |
| TW201600535A (zh) * | 2014-05-28 | 2016-01-01 | Ajinomoto Kk | 聚醚酮化合物 |
| US9308488B1 (en) * | 2014-09-26 | 2016-04-12 | Uop Llc | High permeability polyimide membranes: gas selectivity enhancement through UV treatment |
| KR101726657B1 (ko) | 2014-10-13 | 2017-04-14 | 한국화학연구원 | 피리딘 포함 고 내열 폴리벤즈옥사졸 화합물, 이를 포함하는 유기절연체 필름 조성물 및 이를 이용한 박막 트랜지스터 |
| WO2016137151A1 (fr) * | 2015-02-25 | 2016-09-01 | 한양대학교 산학협력단 | Membrane capillaire de séparation de gaz constituée d'un copolymère de poly(benzoxazole-imide) réarrangé thermiquement, et son procédé de préparation |
| KR20160103810A (ko) | 2015-02-25 | 2016-09-02 | 한양대학교 산학협력단 | 배연가스 분리용 가교구조의 열전환 폴리(벤즈옥사졸-이미드) 공중합체 중공사막 및 그 제조방법 |
| KR101972999B1 (ko) | 2015-02-25 | 2019-04-26 | 한양대학교 산학협력단 | 가교구조의 열전환 폴리(벤즈옥사졸-이미드) 공중합체 중공사 기체분리막 및 그 제조방법 |
| WO2016136404A1 (fr) * | 2015-02-27 | 2016-09-01 | 富士フイルム株式会社 | Membrane de séparation de gaz, module de séparation de gaz, dispositif de séparation de gaz et procédé de séparation de gaz |
| MY186035A (en) * | 2015-11-20 | 2021-06-15 | Uop Llc | High selectivity copolyimide membranes for separations |
| US10919002B2 (en) * | 2018-08-28 | 2021-02-16 | Saudi Arabian Oil Company | Fluorinated polytriazole membrane materials for gas separation technology |
| KR102055343B1 (ko) | 2019-04-19 | 2019-12-12 | 한양대학교 산학협력단 | 가교구조의 열전환 폴리(벤즈옥사졸-이미드) 공중합체 중공사 기체분리막 및 그 제조방법 |
| KR102236277B1 (ko) | 2020-03-11 | 2021-04-02 | 한국화학연구원 | H2o 안정성을 가지는 물의 선택적 분리를 위한 고온 고분자 분리막 및 이를 이용한 반응-분리 하이브리드 시스템 |
| CN112439319B (zh) * | 2020-11-16 | 2022-10-14 | 中蓝晨光化工有限公司 | 一种耐溶剂型pbo纳滤膜及其制备方法 |
| KR20230124319A (ko) | 2022-02-18 | 2023-08-25 | 한국화학연구원 | 반응 수율 향상을 위한 열적 재배열된 고온용 고분자 분리막 및 상기 분리막을 이용한 반응-분리 하이브리드 시스템 |
| KR20240016829A (ko) | 2022-07-29 | 2024-02-06 | 한국화학연구원 | 수성가스 전환 반응 억제를 통한 경질 올레핀의 생산 효율을 증가시키는 피셔-트롭쉬 반응용 반응-분리 하이브리드 시스템 |
| KR20240016830A (ko) | 2022-07-29 | 2024-02-06 | 한국화학연구원 | 물로 인한 촉매 피독을 방지하는 반응-분리 하이브리드 시스템 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4717393A (en) * | 1986-10-27 | 1988-01-05 | E. I. Du Pont De Nemours And Company | Polyimide gas separation membranes |
| JP2984716B2 (ja) * | 1990-08-31 | 1999-11-29 | ダイセル化学工業株式会社 | 芳香族系分離膜 |
| JP2900184B2 (ja) * | 1990-08-31 | 1999-06-02 | ダイセル化学工業株式会社 | 芳香族系共重合分離膜 |
| US5837032A (en) * | 1991-01-30 | 1998-11-17 | The Cynara Company | Gas separations utilizing glassy polymer membranes at sub-ambient temperatures |
| US5409524A (en) * | 1992-12-01 | 1995-04-25 | The Dow Chemical Company | Membranes having improved selectivity and recovery, and process for making same |
| ATE167081T1 (de) * | 1992-12-01 | 1998-06-15 | Mg Generon Inc | Membran mit verbesserter selektivität und rückgewinnung und verfahren zu deren herstellung |
| US6896717B2 (en) * | 2002-07-05 | 2005-05-24 | Membrane Technology And Research, Inc. | Gas separation using coated membranes |
| JP2004231875A (ja) | 2003-01-31 | 2004-08-19 | Toyobo Co Ltd | ポリベンゾオキサゾールフィルムおよびその製造方法 |
| KR100782959B1 (ko) * | 2005-01-25 | 2007-12-11 | 한양대학교 산학협력단 | 다공성 유기 고분자, 이의 제조방법 및 이를 이용한 기체 분리막 |
| US8561812B2 (en) * | 2009-03-27 | 2013-10-22 | Uop Llc | Blend polymer membranes comprising thermally rearranged polymers derived from aromatic polyimides containing ortho-positioned functional groups |
| US7810652B2 (en) * | 2009-09-25 | 2010-10-12 | Uop Llc | Method to improve the selectivity of polybenzoxazole membranes |
-
2010
- 2010-02-22 JP JP2012502061A patent/JP5607721B2/ja not_active Expired - Fee Related
- 2010-02-22 AU AU2010229241A patent/AU2010229241B2/en not_active Ceased
- 2010-02-22 BR BRPI1013695A patent/BRPI1013695A2/pt not_active IP Right Cessation
- 2010-02-22 KR KR1020117024855A patent/KR101392124B1/ko active IP Right Grant
- 2010-02-22 EP EP10756536.8A patent/EP2411130A4/fr not_active Withdrawn
- 2010-02-22 CN CN2010800229646A patent/CN102448593A/zh active Pending
- 2010-02-22 CA CA2755923A patent/CA2755923A1/fr not_active Abandoned
- 2010-02-22 MY MYPI2011004425A patent/MY157509A/en unknown
- 2010-02-22 WO PCT/US2010/024855 patent/WO2010110975A2/fr active Application Filing
Also Published As
| Publication number | Publication date |
|---|---|
| KR101392124B1 (ko) | 2014-05-07 |
| MY157509A (en) | 2016-06-15 |
| WO2010110975A2 (fr) | 2010-09-30 |
| AU2010229241A1 (en) | 2011-10-06 |
| BRPI1013695A2 (pt) | 2016-04-26 |
| CN102448593A (zh) | 2012-05-09 |
| JP5607721B2 (ja) | 2014-10-15 |
| KR20110130503A (ko) | 2011-12-05 |
| WO2010110975A3 (fr) | 2011-02-17 |
| EP2411130A2 (fr) | 2012-02-01 |
| AU2010229241B2 (en) | 2014-09-18 |
| JP2012521871A (ja) | 2012-09-20 |
| EP2411130A4 (fr) | 2015-09-02 |
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| EEER | Examination request | ||
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