CN1293081A - 聚酰亚胺气体分离膜 - Google Patents
聚酰亚胺气体分离膜 Download PDFInfo
- Publication number
- CN1293081A CN1293081A CN00133354.2A CN00133354A CN1293081A CN 1293081 A CN1293081 A CN 1293081A CN 00133354 A CN00133354 A CN 00133354A CN 1293081 A CN1293081 A CN 1293081A
- Authority
- CN
- China
- Prior art keywords
- film
- polyamic acid
- polymer
- paas
- solvent
- 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.)
- Granted
Links
- 229920001721 polyimide Polymers 0.000 title claims abstract description 62
- 239000012528 membrane Substances 0.000 title claims abstract description 55
- 239000004642 Polyimide Substances 0.000 title claims abstract description 40
- 238000000926 separation method Methods 0.000 title abstract description 14
- 229920000642 polymer Polymers 0.000 claims abstract description 106
- 229920005575 poly(amic acid) Polymers 0.000 claims abstract description 68
- 239000002243 precursor Substances 0.000 claims abstract description 50
- 238000000034 method Methods 0.000 claims abstract description 38
- -1 ammonium cations Chemical group 0.000 claims abstract description 34
- 150000003839 salts Chemical class 0.000 claims abstract description 32
- 150000001412 amines Chemical group 0.000 claims abstract description 16
- 239000002904 solvent Substances 0.000 claims description 68
- 239000000203 mixture Substances 0.000 claims description 35
- 150000003512 tertiary amines Chemical class 0.000 claims description 33
- 239000003054 catalyst Substances 0.000 claims description 32
- 239000002131 composite material Substances 0.000 claims description 23
- 239000011248 coating agent Substances 0.000 claims description 21
- 238000000576 coating method Methods 0.000 claims description 21
- 238000010438 heat treatment Methods 0.000 claims description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 20
- 125000003118 aryl group Chemical group 0.000 claims description 14
- 239000000126 substance Substances 0.000 claims description 14
- 239000012024 dehydrating agents Substances 0.000 claims description 13
- 230000015572 biosynthetic process Effects 0.000 claims description 11
- 235000012489 doughnuts Nutrition 0.000 claims description 10
- 125000002723 alicyclic group Chemical group 0.000 claims description 8
- 238000001035 drying Methods 0.000 claims description 8
- 239000012530 fluid Substances 0.000 claims description 8
- 125000000623 heterocyclic group Chemical group 0.000 claims description 8
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 6
- 229920002492 poly(sulfone) Polymers 0.000 claims description 6
- 239000004952 Polyamide Substances 0.000 claims description 5
- 125000001931 aliphatic group Chemical group 0.000 claims description 5
- 229920002647 polyamide Polymers 0.000 claims description 5
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- 229920002873 Polyethylenimine Polymers 0.000 claims description 2
- 238000007654 immersion Methods 0.000 claims description 2
- 229920001601 polyetherimide Polymers 0.000 claims description 2
- 229920000098 polyolefin Polymers 0.000 claims description 2
- 150000001408 amides Chemical class 0.000 claims 1
- 150000001298 alcohols Chemical class 0.000 abstract 1
- 230000002708 enhancing effect Effects 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 47
- 239000007789 gas Substances 0.000 description 44
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 41
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 36
- 238000002360 preparation method Methods 0.000 description 28
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 15
- 150000002500 ions Chemical class 0.000 description 14
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 12
- 239000000835 fiber Substances 0.000 description 12
- 229960003540 oxyquinoline Drugs 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- 238000005266 casting Methods 0.000 description 11
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- 239000000463 material Substances 0.000 description 10
- 238000012545 processing Methods 0.000 description 10
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 8
- 229910052799 carbon Inorganic materials 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 8
- 230000035699 permeability Effects 0.000 description 8
- PTMBWNZJOQBTBK-UHFFFAOYSA-N pyridin-4-ylmethanol Chemical compound OCC1=CC=NC=C1 PTMBWNZJOQBTBK-UHFFFAOYSA-N 0.000 description 8
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 7
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 7
- 239000002253 acid Substances 0.000 description 7
- 150000001721 carbon Chemical group 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 125000000962 organic group Chemical group 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 238000007796 conventional method Methods 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000003960 organic solvent Substances 0.000 description 6
- 238000001556 precipitation Methods 0.000 description 6
- 230000008569 process Effects 0.000 description 6
- 239000000376 reactant Substances 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
- 239000012973 diazabicyclooctane Substances 0.000 description 5
- 238000001704 evaporation Methods 0.000 description 5
- 150000003949 imides Chemical class 0.000 description 5
- 238000001764 infiltration Methods 0.000 description 5
- 230000008595 infiltration Effects 0.000 description 5
- 229920006254 polymer film Polymers 0.000 description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 5
- FZENGILVLUJGJX-NSCUHMNNSA-N (E)-acetaldehyde oxime Chemical compound C\C=N\O FZENGILVLUJGJX-NSCUHMNNSA-N 0.000 description 4
- ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 description 4
- CUYKNJBYIJFRCU-UHFFFAOYSA-N 3-aminopyridine Chemical compound NC1=CC=CN=C1 CUYKNJBYIJFRCU-UHFFFAOYSA-N 0.000 description 4
- NXDMHKQJWIMEEE-UHFFFAOYSA-N 4-(4-aminophenoxy)aniline;furo[3,4-f][2]benzofuran-1,3,5,7-tetrone Chemical compound C1=CC(N)=CC=C1OC1=CC=C(N)C=C1.C1=C2C(=O)OC(=O)C2=CC2=C1C(=O)OC2=O NXDMHKQJWIMEEE-UHFFFAOYSA-N 0.000 description 4
- 229940090248 4-hydroxybenzoic acid Drugs 0.000 description 4
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 4
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 150000008064 anhydrides Chemical class 0.000 description 4
- 150000004982 aromatic amines Chemical class 0.000 description 4
- 230000004888 barrier function Effects 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- WZJYKHNJTSNBHV-UHFFFAOYSA-N benzo[h]quinoline Chemical compound C1=CN=C2C3=CC=CC=C3C=CC2=C1 WZJYKHNJTSNBHV-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000009792 diffusion process Methods 0.000 description 4
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 4
- 150000002460 imidazoles Chemical class 0.000 description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
- YWFWDNVOPHGWMX-UHFFFAOYSA-N n,n-dimethyldodecan-1-amine Chemical compound CCCCCCCCCCCCN(C)C YWFWDNVOPHGWMX-UHFFFAOYSA-N 0.000 description 4
- 235000001968 nicotinic acid Nutrition 0.000 description 4
- 239000011664 nicotinic acid Substances 0.000 description 4
- 229920003223 poly(pyromellitimide-1,4-diphenyl ether) Polymers 0.000 description 4
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 4
- 238000009987 spinning Methods 0.000 description 4
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 4
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 239000004721 Polyphenylene oxide Substances 0.000 description 3
- 230000000996 additive effect Effects 0.000 description 3
- 239000000010 aprotic solvent Substances 0.000 description 3
- 239000012298 atmosphere Substances 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 230000018044 dehydration Effects 0.000 description 3
- 238000006297 dehydration reaction Methods 0.000 description 3
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical group C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 238000006386 neutralization reaction Methods 0.000 description 3
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000011877 solvent mixture Substances 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 3
- 238000001291 vacuum drying Methods 0.000 description 3
- SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 description 2
- DXVHUJPVSOQHQT-UHFFFAOYSA-N 1-oxido-3H-pyridin-1-ium-4-one Chemical compound [N+]=1(C=CC(CC=1)=O)[O-] DXVHUJPVSOQHQT-UHFFFAOYSA-N 0.000 description 2
- YMEZKRMAPQIBQH-UHFFFAOYSA-N 1-oxidopyridin-1-ium-3-ol Chemical class OC1=CC=C[N+]([O-])=C1 YMEZKRMAPQIBQH-UHFFFAOYSA-N 0.000 description 2
- AAQTWLBJPNLKHT-UHFFFAOYSA-N 1H-perimidine Chemical compound N1C=NC2=CC=CC3=CC=CC1=C32 AAQTWLBJPNLKHT-UHFFFAOYSA-N 0.000 description 2
- PDQRQJVPEFGVRK-UHFFFAOYSA-N 2,1,3-benzothiadiazole Chemical compound C1=CC=CC2=NSN=C21 PDQRQJVPEFGVRK-UHFFFAOYSA-N 0.000 description 2
- SNTWKPAKVQFCCF-UHFFFAOYSA-N 2,3-dihydro-1h-triazole Chemical compound N1NC=CN1 SNTWKPAKVQFCCF-UHFFFAOYSA-N 0.000 description 2
- CSDSSGBPEUDDEE-UHFFFAOYSA-N 2-formylpyridine Chemical compound O=CC1=CC=CC=N1 CSDSSGBPEUDDEE-UHFFFAOYSA-N 0.000 description 2
- YPWSASPSYAWQRK-UHFFFAOYSA-N 2-pyridin-3-ylethanol Chemical compound OCCC1=CC=CN=C1 YPWSASPSYAWQRK-UHFFFAOYSA-N 0.000 description 2
- DWPYQDGDWBKJQL-UHFFFAOYSA-N 2-pyridin-4-ylethanol Chemical compound OCCC1=CC=NC=C1 DWPYQDGDWBKJQL-UHFFFAOYSA-N 0.000 description 2
- RMHQDKYZXJVCME-UHFFFAOYSA-N 2-pyridin-4-ylpyridine Chemical group N1=CC=CC=C1C1=CC=NC=C1 RMHQDKYZXJVCME-UHFFFAOYSA-N 0.000 description 2
- WPTCSQBWLUUYDV-UHFFFAOYSA-N 2-quinolin-2-ylquinoline Chemical compound C1=CC=CC2=NC(C3=NC4=CC=CC=C4C=C3)=CC=C21 WPTCSQBWLUUYDV-UHFFFAOYSA-N 0.000 description 2
- QLILRKBRWXALIE-UHFFFAOYSA-N 3-nitropyridine Chemical compound [O-][N+](=O)C1=CC=CN=C1 QLILRKBRWXALIE-UHFFFAOYSA-N 0.000 description 2
- MVQVNTPHUGQQHK-UHFFFAOYSA-N 3-pyridinemethanol Chemical compound OCC1=CC=CN=C1 MVQVNTPHUGQQHK-UHFFFAOYSA-N 0.000 description 2
- GRFNBEZIAWKNCO-UHFFFAOYSA-N 3-pyridinol Chemical compound OC1=CC=CN=C1 GRFNBEZIAWKNCO-UHFFFAOYSA-N 0.000 description 2
- HCCNHYWZYYIOFM-UHFFFAOYSA-N 3h-benzo[e]benzimidazole Chemical class C1=CC=C2C(N=CN3)=C3C=CC2=C1 HCCNHYWZYYIOFM-UHFFFAOYSA-N 0.000 description 2
- MWVTWFVJZLCBMC-UHFFFAOYSA-N 4,4'-bipyridine Chemical group C1=NC=CC(C=2C=CN=CC=2)=C1 MWVTWFVJZLCBMC-UHFFFAOYSA-N 0.000 description 2
- NUKYPUAOHBNCPY-UHFFFAOYSA-N 4-aminopyridine Chemical compound NC1=CC=NC=C1 NUKYPUAOHBNCPY-UHFFFAOYSA-N 0.000 description 2
- GCNTZFIIOFTKIY-UHFFFAOYSA-N 4-hydroxypyridine Chemical compound OC1=CC=NC=C1 GCNTZFIIOFTKIY-UHFFFAOYSA-N 0.000 description 2
- LPULCTXGGDJCTO-UHFFFAOYSA-N 6-methylheptan-1-amine Chemical compound CC(C)CCCCCN LPULCTXGGDJCTO-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 2
- MTFJSAGADRTKCI-UHFFFAOYSA-N N-(pyridin-2-ylmethylidene)hydroxylamine Chemical compound ON=CC1=CC=CC=N1 MTFJSAGADRTKCI-UHFFFAOYSA-N 0.000 description 2
- GQLSEYOOXBRDFZ-UHFFFAOYSA-N N-formylnornicotine Natural products O=CN1CCCC1C1=CC=CN=C1 GQLSEYOOXBRDFZ-UHFFFAOYSA-N 0.000 description 2
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- SIOXPEMLGUPBBT-UHFFFAOYSA-N Picolinic acid Natural products OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 description 2
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 2
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 2
- 150000008065 acid anhydrides Chemical class 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000004760 aramid Substances 0.000 description 2
- 229920003235 aromatic polyamide Polymers 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- DMMLYDCVMZEUMT-UHFFFAOYSA-N benzo[h]cinnoline Chemical compound C1=NN=C2C3=CC=CC=C3C=CC2=C1 DMMLYDCVMZEUMT-UHFFFAOYSA-N 0.000 description 2
- FZICDBOJOMQACG-UHFFFAOYSA-N benzo[h]isoquinoline Chemical compound C1=NC=C2C3=CC=CC=C3C=CC2=C1 FZICDBOJOMQACG-UHFFFAOYSA-N 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- 150000001854 cinnolines Chemical class 0.000 description 2
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 2
- 230000002950 deficient Effects 0.000 description 2
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 229960004979 fampridine Drugs 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 239000006260 foam Substances 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- ANSXAPJVJOKRDJ-UHFFFAOYSA-N furo[3,4-f][2]benzofuran-1,3,5,7-tetrone Chemical compound C1=C2C(=O)OC(=O)C2=CC2=C1C(=O)OC2=O ANSXAPJVJOKRDJ-UHFFFAOYSA-N 0.000 description 2
- WEANOYWKRLELRV-UHFFFAOYSA-N hexadecyl-dimethyl-propan-2-ylazanium Chemical compound CCCCCCCCCCCCCCCC[N+](C)(C)C(C)C WEANOYWKRLELRV-UHFFFAOYSA-N 0.000 description 2
- 150000001261 hydroxy acids Chemical group 0.000 description 2
- TWBYWOBDOCUKOW-UHFFFAOYSA-M isonicotinate Chemical compound [O-]C(=O)C1=CC=NC=C1 TWBYWOBDOCUKOW-UHFFFAOYSA-M 0.000 description 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- CRVGTESFCCXCTH-UHFFFAOYSA-N methyl diethanolamine Chemical compound OCCN(C)CCO CRVGTESFCCXCTH-UHFFFAOYSA-N 0.000 description 2
- WTXHURQURAIMNT-UHFFFAOYSA-N n,n-diethylpyrazine-2-carboxamide Chemical compound CCN(CC)C(=O)C1=CN=CC=N1 WTXHURQURAIMNT-UHFFFAOYSA-N 0.000 description 2
- QMHNQZGXPNCMCO-UHFFFAOYSA-N n,n-dimethylhexan-1-amine Chemical compound CCCCCCN(C)C QMHNQZGXPNCMCO-UHFFFAOYSA-N 0.000 description 2
- AGPFOBMNLCROLG-UHFFFAOYSA-N n,n-dimethylpyrazine-2-carboxamide Chemical compound CN(C)C(=O)C1=CN=CC=N1 AGPFOBMNLCROLG-UHFFFAOYSA-N 0.000 description 2
- 150000005054 naphthyridines Chemical class 0.000 description 2
- 239000003345 natural gas Substances 0.000 description 2
- 235000005152 nicotinamide Nutrition 0.000 description 2
- 239000011570 nicotinamide Substances 0.000 description 2
- 229960003966 nicotinamide Drugs 0.000 description 2
- 229960002715 nicotine Drugs 0.000 description 2
- SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 description 2
- 229960003512 nicotinic acid Drugs 0.000 description 2
- 229960003226 nikethamide Drugs 0.000 description 2
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Images
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D71/00—Semi-permeable membranes for separation processes or apparatus characterised by the material; Manufacturing processes specially adapted therefor
- B01D71/06—Organic material
- B01D71/58—Other polymers having nitrogen in the main chain, with or without oxygen or carbon only
- B01D71/62—Polycondensates having nitrogen-containing heterocyclic rings in the main chain
- B01D71/64—Polyimides; Polyamide-imides; Polyester-imides; Polyamide acids or similar polyimide precursors
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D53/00—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols
- B01D53/22—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols by diffusion
- B01D53/228—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols by diffusion characterised by specific membranes
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D69/00—Semi-permeable membranes for separation processes or apparatus characterised by their form, structure or properties; Manufacturing processes specially adapted therefor
- B01D69/12—Composite membranes; Ultra-thin membranes
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D71/00—Semi-permeable membranes for separation processes or apparatus characterised by the material; Manufacturing processes specially adapted therefor
- B01D71/06—Organic material
- B01D71/76—Macromolecular material not specifically provided for in a single one of groups B01D71/08 - B01D71/74
- B01D71/82—Macromolecular material not specifically provided for in a single one of groups B01D71/08 - B01D71/74 characterised by the presence of specified groups, e.g. introduced by chemical after-treatment
-
- 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
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Analytical Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Separation Using Semi-Permeable Membranes (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
Abstract
Description
Claims (10)
Applications Claiming Priority (6)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US09/404724 | 1999-09-24 | ||
US09/404,724 US6497747B1 (en) | 1999-09-24 | 1999-09-24 | Production and use of improved polyimide separation membranes |
US09/404,724 | 1999-09-24 | ||
US09/661902 | 2000-09-14 | ||
US09/661,902 | 2000-09-14 | ||
US09/661,902 US6790263B1 (en) | 1999-09-24 | 2000-09-14 | Polymide gas separation membranes |
Publications (2)
Publication Number | Publication Date |
---|---|
CN1293081A true CN1293081A (zh) | 2001-05-02 |
CN1278763C CN1278763C (zh) | 2006-10-11 |
Family
ID=27018746
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN00133354.2A Expired - Fee Related CN1278763C (zh) | 1999-09-24 | 2000-09-22 | 聚酰亚胺气体分离膜 |
Country Status (2)
Country | Link |
---|---|
EP (1) | EP1086973A3 (zh) |
CN (1) | CN1278763C (zh) |
Cited By (7)
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CN101925398A (zh) * | 2008-02-05 | 2010-12-22 | 宇部兴产株式会社 | 聚酰亚胺气体分离膜和气体分离方法 |
CN101676321B (zh) * | 2008-09-18 | 2011-10-12 | 比亚迪股份有限公司 | 一种聚酰亚胺膜的制备方法 |
CN103531812A (zh) * | 2013-09-26 | 2014-01-22 | 东莞新能源科技有限公司 | 锂离子二次电池及其负极片 |
CN106637472A (zh) * | 2016-11-29 | 2017-05-10 | 江西师范大学 | 电纺法制备聚酰亚胺微米纤维的方法 |
CN106669433A (zh) * | 2016-12-29 | 2017-05-17 | 浙江海洋大学 | 一种用于浮顶油罐二次密封的油气分离膜 |
WO2019165597A1 (en) * | 2018-02-28 | 2019-09-06 | Evonik (Shanghai) Investment Management Co., Ltd. | Functionalized polyimides and membranes for gas separations |
CN112961348A (zh) * | 2021-03-17 | 2021-06-15 | 中国科学院宁波材料技术与工程研究所 | 一种高断裂伸长率的聚酰亚胺膜的制备方法 |
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Publication number | Priority date | Publication date | Assignee | Title |
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EP1095695A3 (en) * | 1999-09-24 | 2001-11-21 | Praxair Technology, Inc. | Novel polyimide amic acid salts and polyimide membranes formed therefrom |
US6497747B1 (en) * | 1999-09-24 | 2002-12-24 | Praxair Technology, Inc. | Production and use of improved polyimide separation membranes |
DE102006034601B3 (de) * | 2006-07-26 | 2008-02-07 | Schmidt, Klaus, Prof. Dr. | Rückhaltung von Edelgasen im Atemgas bei beatmeten Patienten mit Hilfe von Membranseparation |
WO2014094139A1 (en) | 2012-12-22 | 2014-06-26 | Dmf Medical Incorporated | An anesthetic circuit having a hollow fiber membrane |
CN107124886A (zh) * | 2014-12-31 | 2017-09-01 | 沙特基础工业全球技术有限公司 | 形成聚酰亚胺的组合物、制备方法及由其制备的制品 |
CN110604175B (zh) * | 2019-10-28 | 2022-04-12 | 中国农业科学院农产品加工研究所 | 抑制粮食中黄曲霉生长及毒素产生的方法 |
KR102621031B1 (ko) * | 2021-06-29 | 2024-01-05 | 한국화학연구원 | 폴리아믹산 수용액 조성물 |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5348569A (en) * | 1993-06-30 | 1994-09-20 | Praxair Technology, Inc. | Modified poly(phenylene oxide) based membranes for enhanced fluid separation |
DE69622088T2 (de) * | 1995-06-06 | 2003-03-06 | Ube Industries, Ltd. | Aromatische Polyimid und Gastrennung |
US5725633A (en) * | 1995-06-30 | 1998-03-10 | Praxair Technology, Inc. | Sulfonated polyimide gas separation membranes |
US5618334A (en) * | 1995-06-30 | 1997-04-08 | Praxair Technology, Inc. | Sulfonated polyimide gas separation membranes |
EP1095695A3 (en) * | 1999-09-24 | 2001-11-21 | Praxair Technology, Inc. | Novel polyimide amic acid salts and polyimide membranes formed therefrom |
US6497747B1 (en) * | 1999-09-24 | 2002-12-24 | Praxair Technology, Inc. | Production and use of improved polyimide separation membranes |
-
2000
- 2000-09-22 CN CN00133354.2A patent/CN1278763C/zh not_active Expired - Fee Related
- 2000-09-22 EP EP00120771A patent/EP1086973A3/en not_active Withdrawn
Cited By (12)
Publication number | Priority date | Publication date | Assignee | Title |
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CN101925398A (zh) * | 2008-02-05 | 2010-12-22 | 宇部兴产株式会社 | 聚酰亚胺气体分离膜和气体分离方法 |
US8394176B2 (en) | 2008-02-05 | 2013-03-12 | Ube Industries, Ltd. | Polyimide gas separation membrane and gas separation method |
CN101925398B (zh) * | 2008-02-05 | 2013-06-26 | 宇部兴产株式会社 | 聚酰亚胺气体分离膜和气体分离方法 |
CN101676321B (zh) * | 2008-09-18 | 2011-10-12 | 比亚迪股份有限公司 | 一种聚酰亚胺膜的制备方法 |
CN103531812A (zh) * | 2013-09-26 | 2014-01-22 | 东莞新能源科技有限公司 | 锂离子二次电池及其负极片 |
CN103531812B (zh) * | 2013-09-26 | 2018-02-27 | 东莞新能源科技有限公司 | 锂离子二次电池及其负极片 |
CN106637472A (zh) * | 2016-11-29 | 2017-05-10 | 江西师范大学 | 电纺法制备聚酰亚胺微米纤维的方法 |
CN106669433A (zh) * | 2016-12-29 | 2017-05-17 | 浙江海洋大学 | 一种用于浮顶油罐二次密封的油气分离膜 |
WO2019165597A1 (en) * | 2018-02-28 | 2019-09-06 | Evonik (Shanghai) Investment Management Co., Ltd. | Functionalized polyimides and membranes for gas separations |
CN111918712A (zh) * | 2018-02-28 | 2020-11-10 | 赢创(上海)投资管理有限公司 | 官能化聚酰亚胺和气体分离用膜 |
CN112961348A (zh) * | 2021-03-17 | 2021-06-15 | 中国科学院宁波材料技术与工程研究所 | 一种高断裂伸长率的聚酰亚胺膜的制备方法 |
CN112961348B (zh) * | 2021-03-17 | 2022-08-05 | 中国科学院宁波材料技术与工程研究所 | 一种高断裂伸长率的聚酰亚胺膜的制备方法 |
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