JP4249138B2 - ガス分離膜用のポリイミドブレンド - Google Patents
ガス分離膜用のポリイミドブレンド Download PDFInfo
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- JP4249138B2 JP4249138B2 JP2004570707A JP2004570707A JP4249138B2 JP 4249138 B2 JP4249138 B2 JP 4249138B2 JP 2004570707 A JP2004570707 A JP 2004570707A JP 2004570707 A JP2004570707 A JP 2004570707A JP 4249138 B2 JP4249138 B2 JP 4249138B2
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- chemical formula
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- 239000000203 mixture Substances 0.000 title claims abstract description 121
- 239000012528 membrane Substances 0.000 title claims abstract description 111
- 238000000926 separation method Methods 0.000 title claims description 42
- 239000004642 Polyimide Substances 0.000 title description 36
- 229920001721 polyimide Polymers 0.000 title description 36
- 239000000126 substance Substances 0.000 claims abstract description 70
- 229920000642 polymer Polymers 0.000 claims abstract description 48
- 238000000034 method Methods 0.000 claims abstract description 16
- 239000007789 gas Substances 0.000 claims description 87
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 18
- 239000012466 permeate Substances 0.000 claims description 17
- 239000012510 hollow fiber Substances 0.000 claims description 14
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 12
- 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 claims description 11
- GTDPSWPPOUPBNX-UHFFFAOYSA-N ac1mqpva Chemical compound CC12C(=O)OC(=O)C1(C)C1(C)C2(C)C(=O)OC1=O GTDPSWPPOUPBNX-UHFFFAOYSA-N 0.000 claims description 9
- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 9
- 239000001569 carbon dioxide Substances 0.000 claims description 9
- VLDPXPPHXDGHEW-UHFFFAOYSA-N 1-chloro-2-dichlorophosphoryloxybenzene Chemical compound ClC1=CC=CC=C1OP(Cl)(Cl)=O VLDPXPPHXDGHEW-UHFFFAOYSA-N 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 claims description 5
- 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 claims description 4
- -1 1- (trifluoromethyl) ethylidene Chemical group 0.000 claims description 3
- 238000006068 polycondensation reaction Methods 0.000 claims description 3
- LADVLFVCTCHOAI-UHFFFAOYSA-N isocyanic acid;toluene Chemical compound N=C=O.CC1=CC=CC=C1 LADVLFVCTCHOAI-UHFFFAOYSA-N 0.000 claims description 2
- 230000008569 process Effects 0.000 claims description 2
- 239000012465 retentate Substances 0.000 claims description 2
- 230000000295 complement effect Effects 0.000 claims 2
- ZVDSMYGTJDFNHN-UHFFFAOYSA-N 2,4,6-trimethylbenzene-1,3-diamine Chemical group CC1=CC(C)=C(N)C(C)=C1N ZVDSMYGTJDFNHN-UHFFFAOYSA-N 0.000 claims 1
- ZHBXLZQQVCDGPA-UHFFFAOYSA-N 5-[(1,3-dioxo-2-benzofuran-5-yl)sulfonyl]-2-benzofuran-1,3-dione Chemical compound C1=C2C(=O)OC(=O)C2=CC(S(=O)(=O)C=2C=C3C(=O)OC(C3=CC=2)=O)=C1 ZHBXLZQQVCDGPA-UHFFFAOYSA-N 0.000 claims 1
- 150000004982 aromatic amines Chemical class 0.000 claims 1
- WKDNYTOXBCRNPV-UHFFFAOYSA-N bpda Chemical compound C1=C2C(=O)OC(=O)C2=CC(C=2C=C3C(=O)OC(C3=CC=2)=O)=C1 WKDNYTOXBCRNPV-UHFFFAOYSA-N 0.000 claims 1
- 238000006482 condensation reaction Methods 0.000 claims 1
- 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 claims 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 claims 1
- 230000035699 permeability Effects 0.000 abstract description 29
- 239000000835 fiber Substances 0.000 description 27
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 24
- 239000010408 film Substances 0.000 description 24
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 239000000243 solution Substances 0.000 description 15
- 239000002904 solvent Substances 0.000 description 14
- 230000000052 comparative effect Effects 0.000 description 13
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 229920002959 polymer blend Polymers 0.000 description 10
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
- 239000000463 material Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 0 C*CC1CC(C(C)C)=CC1 Chemical compound C*CC1CC(C(C)C)=CC1 0.000 description 6
- 239000002131 composite material Substances 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 150000004985 diamines Chemical class 0.000 description 5
- 230000009477 glass transition Effects 0.000 description 5
- 229920006254 polymer film Polymers 0.000 description 5
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 4
- 238000009833 condensation Methods 0.000 description 4
- 230000004907 flux Effects 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 4
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 3
- 239000004936 P-84 Substances 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 230000007547 defect Effects 0.000 description 3
- 125000005442 diisocyanate group Chemical group 0.000 description 3
- 229920005597 polymer membrane Polymers 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 230000002195 synergetic effect Effects 0.000 description 3
- 230000008901 benefit Effects 0.000 description 2
- 230000005540 biological transmission Effects 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000003345 natural gas Substances 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 238000009987 spinning Methods 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- CFKDJXPNRVRJBC-UHFFFAOYSA-N 1-phenyl-2,3-dihydroindene-1,2-diamine Chemical compound NC1CC2=CC=CC=C2C1(N)C1=CC=CC=C1 CFKDJXPNRVRJBC-UHFFFAOYSA-N 0.000 description 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- QHHKLPCQTTWFSS-UHFFFAOYSA-N 5-[2-(1,3-dioxo-2-benzofuran-5-yl)-1,1,1,3,3,3-hexafluoropropan-2-yl]-2-benzofuran-1,3-dione Chemical compound C1=C2C(=O)OC(=O)C2=CC(C(C=2C=C3C(=O)OC(=O)C3=CC=2)(C(F)(F)F)C(F)(F)F)=C1 QHHKLPCQTTWFSS-UHFFFAOYSA-N 0.000 description 1
- 206010000117 Abnormal behaviour Diseases 0.000 description 1
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 1
- 239000006057 Non-nutritive feed additive Substances 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
- 239000004952 Polyamide Substances 0.000 description 1
- FHKPLLOSJHHKNU-INIZCTEOSA-N [(3S)-3-[8-(1-ethyl-5-methylpyrazol-4-yl)-9-methylpurin-6-yl]oxypyrrolidin-1-yl]-(oxan-4-yl)methanone Chemical compound C(C)N1N=CC(=C1C)C=1N(C2=NC=NC(=C2N=1)O[C@@H]1CN(CC1)C(=O)C1CCOCC1)C FHKPLLOSJHHKNU-INIZCTEOSA-N 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000004984 aromatic diamines Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 229920005622 compatible polymer blend Polymers 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 230000009849 deactivation Effects 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 125000006159 dianhydride group Chemical group 0.000 description 1
- 238000000113 differential scanning calorimetry Methods 0.000 description 1
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 238000010035 extrusion spinning Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920005575 poly(amic acid) Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920006149 polyester-amide block copolymer Polymers 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000003017 thermal stabilizer Substances 0.000 description 1
- 229920005992 thermoplastic resin Polymers 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 238000000108 ultra-filtration Methods 0.000 description 1
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
-
- 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
- C08L79/08—Polyimides; Polyester-imides; Polyamide-imides; 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
- C08L2205/02—Polymer mixtures characterised by other features containing two or more polymers of the same C08L -group
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02C—CAPTURE, STORAGE, SEQUESTRATION OR DISPOSAL OF GREENHOUSE GASES [GHG]
- Y02C20/00—Capture or disposal of greenhouse gases
- Y02C20/40—Capture or disposal of greenhouse gases of CO2
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US43027502P | 2002-12-02 | 2002-12-02 | |
| US10/642,407 US7018445B2 (en) | 2002-12-02 | 2003-08-15 | Polyimide blends for gas separation membranes |
| PCT/IB2003/004769 WO2004050223A2 (en) | 2002-12-02 | 2003-10-27 | Polyimide blends for gas separation membranes |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2006507939A JP2006507939A (ja) | 2006-03-09 |
| JP4249138B2 true JP4249138B2 (ja) | 2009-04-02 |
Family
ID=32474562
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2004570707A Expired - Lifetime JP4249138B2 (ja) | 2002-12-02 | 2003-10-27 | ガス分離膜用のポリイミドブレンド |
Country Status (8)
Families Citing this family (53)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2435538A1 (en) * | 2003-07-18 | 2005-01-18 | Universite Laval | Solvent resistant asymmetric integrally skinned membranes |
| US7527673B2 (en) * | 2004-03-26 | 2009-05-05 | L'air Liquide, Societe Anonyme A Directoire Et Conseil De Surveillance Pour L'etude Et L'exploitation Des Procedes Georges Claude | Polyimide based mixed matrix composite membranes |
| US20050230305A1 (en) * | 2004-03-26 | 2005-10-20 | Kulkarni Sudhir S | Novel method for forming a mixed matrix composite membrane using washed molecular sieve particles |
| US20050268782A1 (en) * | 2004-03-26 | 2005-12-08 | Kulkarni Sudhir S | Novel polyimide based mixed matrix membranes |
| US7476636B2 (en) * | 2004-12-03 | 2009-01-13 | L'air Liquide, Societe Anonyme A Directoire Et Conseil De Surveillance Pour L'etude Et L'exploration Des Procedes Georges Claude | Method of making mixed matrix membranes using electrostatically stabilized suspensions |
| US7393383B2 (en) * | 2005-01-14 | 2008-07-01 | L'air Liquide, Societe Anonyme A Directoire Et Conseil De Surveillance Pour L'etude Et L'exploitation Des Procedes Georges Claude | Separation membrane made from blends of polyimide with polyamide or polyimide-amide polymers |
| JP5119596B2 (ja) * | 2005-01-21 | 2013-01-16 | 宇部興産株式会社 | 多成分ポリイミドからなるポリイミド非対称膜の製造方法 |
| US8101009B2 (en) * | 2005-03-02 | 2012-01-24 | L'air Liquide Societe Anonyme Pour L'etude Et L'exploitation Des Procedes Georges Claude | Separation membrane by controlled annealing of polyimide polymers |
| US7422623B2 (en) * | 2005-03-02 | 2008-09-09 | L'air Liquide, Societe Anonyme A Directoire Et Conseil De Surveillance Pour L'etude Et L'exploitation Des Procedes Georges Claude | Separation membrane by controlled annealing of polyimide polymers |
| US7485173B1 (en) | 2005-12-15 | 2009-02-03 | Uop Llc | Cross-linkable and cross-linked mixed matrix membranes and methods of making the same |
| US7897207B2 (en) * | 2006-03-10 | 2011-03-01 | Uop Llc | Nano-molecular sieve-polymer mixed matrix membranes with significantly improved gas separation performance |
| US20070209505A1 (en) * | 2006-03-10 | 2007-09-13 | Chunqing Liu | High Flux Mixed Matrix Membranes for Separations |
| US8083833B2 (en) * | 2006-03-10 | 2011-12-27 | Uop Llc | Flexible template-directed microporous partially pyrolyzed polymeric membranes |
| US7846496B2 (en) * | 2006-03-10 | 2010-12-07 | Uop Llc | Mixed matrix membranes incorporating surface-functionalized molecular sieve nanoparticles and methods for making the same |
| US7637983B1 (en) | 2006-06-30 | 2009-12-29 | Uop Llc | Metal organic framework—polymer mixed matrix membranes |
| US7803214B2 (en) * | 2006-07-21 | 2010-09-28 | Ube Industries, Ltd. | Asymmetric hollow-fiber gas separation membrane, gas separation method and gas separation membrane module |
| CN101495548B (zh) * | 2006-07-23 | 2012-01-25 | 宇部兴产株式会社 | 由多成分聚酰亚胺形成的聚酰亚胺膜及其制造方法 |
| US7758751B1 (en) | 2006-11-29 | 2010-07-20 | Uop Llc | UV-cross-linked membranes from polymers of intrinsic microporosity for liquid separations |
| US20080142440A1 (en) * | 2006-12-18 | 2008-06-19 | Chunqing Liu | Liquid Separations Using High Performance Mixed Matrix Membranes |
| US20080143014A1 (en) * | 2006-12-18 | 2008-06-19 | Man-Wing Tang | Asymmetric Gas Separation Membranes with Superior Capabilities for Gas Separation |
| US7998246B2 (en) | 2006-12-18 | 2011-08-16 | Uop Llc | Gas separations using high performance mixed matrix membranes |
| US7815712B2 (en) * | 2006-12-18 | 2010-10-19 | Uop Llc | Method of making high performance mixed matrix membranes using suspensions containing polymers and polymer stabilized molecular sieves |
| US7875758B2 (en) | 2007-01-08 | 2011-01-25 | L'air Liquide, Societe Anonyme Pour L'etude Et L'exploitation Des Procedes George Claude | Systems and methods for the separation of propylene and propane |
| US20080296527A1 (en) * | 2007-06-01 | 2008-12-04 | Chunqing Liu | Uv cross-linked polymer functionalized molecular sieve/polymer mixed matrix membranes |
| US20080300336A1 (en) * | 2007-06-01 | 2008-12-04 | Chunqing Liu | Uv cross-linked polymer functionalized molecular sieve/polymer mixed matrix membranes |
| US20080295691A1 (en) * | 2007-06-01 | 2008-12-04 | Chunqing Liu | Uv cross-linked polymer functionalized molecular sieve/polymer mixed matrix membranes |
| CN101910314A (zh) * | 2007-11-05 | 2010-12-08 | Co2Crc技术股份有限公司 | 气体分离膜及其制备方法 |
| US8337598B2 (en) | 2008-09-05 | 2012-12-25 | Honeywell International Inc. | Photo-crosslinked gas selective membranes as part of thin film composite hollow fiber membranes |
| US7950529B2 (en) * | 2008-09-30 | 2011-05-31 | L'air Liquide Societe Anonyme Pour L'etude Et L'exploitation Des Procedes Georges Claude | Separation membrane made from blends of polyimides with polyimidazoles |
| JP5627198B2 (ja) * | 2009-05-27 | 2014-11-19 | 日東電工株式会社 | プロトン伝導性高分子電解質膜とそれを用いた膜−電極接合体および高分子電解質型燃料電池 |
| US20120123079A1 (en) | 2009-07-23 | 2012-05-17 | Evonik Fibres Gmbh | Polyimide membranes made of polymerization solutions |
| US20110077446A1 (en) | 2009-09-30 | 2011-03-31 | American Air Liquide, Inc. | Membrane Separation of a Mixture of Close Boiling Hydrocarbon Components |
| US20110138999A1 (en) * | 2009-12-15 | 2011-06-16 | Uop Llc | Metal organic framework polymer mixed matrix membranes |
| WO2011129769A1 (en) | 2010-04-12 | 2011-10-20 | National University Of Singapore | Polyimide membranes and their preparation |
| US8366804B2 (en) * | 2010-05-28 | 2013-02-05 | Uop Llc | High permeance polyimide membranes for air separation |
| EP2624935A1 (en) | 2010-10-06 | 2013-08-14 | L'Air Liquide Société Anonyme pour l'Etude et l'Exploitation des Procédés Georges Claude | Carbon dioxide removal process |
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| CN112870983B (zh) * | 2021-01-14 | 2022-05-24 | 清华大学 | 一种用于从有机溶剂中解吸co2的聚酰亚胺膜的制备方法 |
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-
2003
- 2003-08-15 US US10/642,407 patent/US7018445B2/en not_active Expired - Lifetime
- 2003-10-27 CA CA2500346A patent/CA2500346C/en not_active Expired - Lifetime
- 2003-10-27 EP EP03769717A patent/EP1567250B1/en not_active Expired - Lifetime
- 2003-10-27 WO PCT/IB2003/004769 patent/WO2004050223A2/en active Application Filing
- 2003-10-27 DE DE60327461T patent/DE60327461D1/de not_active Expired - Lifetime
- 2003-10-27 AU AU2003278411A patent/AU2003278411A1/en not_active Abandoned
- 2003-10-27 JP JP2004570707A patent/JP4249138B2/ja not_active Expired - Lifetime
- 2003-10-27 AT AT03769717T patent/ATE429971T1/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| CA2500346C (en) | 2012-07-17 |
| JP2006507939A (ja) | 2006-03-09 |
| CA2500346A1 (en) | 2004-06-17 |
| AU2003278411A8 (en) | 2004-06-23 |
| ATE429971T1 (de) | 2009-05-15 |
| US20040107830A1 (en) | 2004-06-10 |
| EP1567250A2 (en) | 2005-08-31 |
| WO2004050223A3 (en) | 2005-04-28 |
| US7018445B2 (en) | 2006-03-28 |
| DE60327461D1 (de) | 2009-06-10 |
| AU2003278411A1 (en) | 2004-06-23 |
| WO2004050223A2 (en) | 2004-06-17 |
| EP1567250B1 (en) | 2009-04-29 |
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