DE3842093A1 - Semipermeable membran aus polybenzoxazol zur trennung von gasen - Google Patents
Semipermeable membran aus polybenzoxazol zur trennung von gasenInfo
- Publication number
- DE3842093A1 DE3842093A1 DE3842093A DE3842093A DE3842093A1 DE 3842093 A1 DE3842093 A1 DE 3842093A1 DE 3842093 A DE3842093 A DE 3842093A DE 3842093 A DE3842093 A DE 3842093A DE 3842093 A1 DE3842093 A1 DE 3842093A1
- Authority
- DE
- Germany
- Prior art keywords
- gas
- general formula
- group
- membrane
- polybenzoxazole
- 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.)
- Withdrawn
Links
- 239000007789 gas Substances 0.000 title claims abstract description 74
- 239000012528 membrane Substances 0.000 title claims abstract description 52
- 229920002577 polybenzoxazole Polymers 0.000 title claims abstract description 28
- 238000000926 separation method Methods 0.000 title claims description 13
- 125000003118 aryl group Chemical group 0.000 claims abstract description 19
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 8
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims abstract description 5
- 229910002092 carbon dioxide Inorganic materials 0.000 claims abstract 2
- 239000001569 carbon dioxide Substances 0.000 claims abstract 2
- 239000000203 mixture Substances 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 16
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 13
- 230000035699 permeability Effects 0.000 claims description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 9
- 229910001873 dinitrogen Inorganic materials 0.000 claims description 5
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 4
- 229910001882 dioxygen Inorganic materials 0.000 claims description 4
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 claims description 3
- 125000004957 naphthylene group Chemical group 0.000 claims description 3
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract description 5
- 239000001301 oxygen Substances 0.000 abstract description 5
- 229910052760 oxygen Inorganic materials 0.000 abstract description 5
- OWQNOTOYTSUHNE-UHFFFAOYSA-N carbon dioxide methane Chemical compound C.C(=O)=O.C OWQNOTOYTSUHNE-UHFFFAOYSA-N 0.000 abstract 1
- 239000004952 Polyamide Substances 0.000 description 20
- 229920002647 polyamide Polymers 0.000 description 20
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 11
- 150000004984 aromatic diamines Chemical class 0.000 description 11
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 239000004760 aramid Substances 0.000 description 9
- 229920003235 aromatic polyamide Polymers 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 8
- 239000003960 organic solvent Substances 0.000 description 7
- 229920000642 polymer Polymers 0.000 description 7
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 6
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- -1 dicarboxylic acid diester Chemical class 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- 230000018044 dehydration Effects 0.000 description 3
- 238000006297 dehydration reaction Methods 0.000 description 3
- 239000011888 foil Substances 0.000 description 3
- 238000007363 ring formation reaction Methods 0.000 description 3
- 229920002050 silicone resin Polymers 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- WDAIEUUMGUXKIK-UHFFFAOYSA-N 5-[1,1,1,3,3,3-hexafluoro-2-[3-(trimethylsilylamino)-4-trimethylsilyloxyphenyl]propan-2-yl]-n-trimethylsilyl-2-trimethylsilyloxyaniline Chemical compound C1=C(O[Si](C)(C)C)C(N[Si](C)(C)C)=CC(C(C=2C=C(N[Si](C)(C)C)C(O[Si](C)(C)C)=CC=2)(C(F)(F)F)C(F)(F)F)=C1 WDAIEUUMGUXKIK-UHFFFAOYSA-N 0.000 description 2
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 229910002091 carbon monoxide Inorganic materials 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 229920002301 cellulose acetate Polymers 0.000 description 2
- 150000001991 dicarboxylic acids Chemical class 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 229920001721 polyimide Polymers 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 235000012239 silicon dioxide Nutrition 0.000 description 2
- 238000010183 spectrum analysis Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- NSGXIBWMJZWTPY-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropane Chemical compound FC(F)(F)CC(F)(F)F NSGXIBWMJZWTPY-UHFFFAOYSA-N 0.000 description 1
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
- UTYHQSKRFPHMQQ-UHFFFAOYSA-N 2-amino-4-(3-amino-4-hydroxyphenoxy)phenol Chemical compound C1=C(O)C(N)=CC(OC=2C=C(N)C(O)=CC=2)=C1 UTYHQSKRFPHMQQ-UHFFFAOYSA-N 0.000 description 1
- PZSYWQSQWUHYRT-UHFFFAOYSA-N 2-amino-4-(3-amino-4-hydroxyphenyl)sulfanylphenol Chemical compound C1=C(O)C(N)=CC(SC=2C=C(N)C(O)=CC=2)=C1 PZSYWQSQWUHYRT-UHFFFAOYSA-N 0.000 description 1
- KECOIASOKMSRFT-UHFFFAOYSA-N 2-amino-4-(3-amino-4-hydroxyphenyl)sulfonylphenol Chemical compound C1=C(O)C(N)=CC(S(=O)(=O)C=2C=C(N)C(O)=CC=2)=C1 KECOIASOKMSRFT-UHFFFAOYSA-N 0.000 description 1
- KCFVSHSJPIVGCG-UHFFFAOYSA-N 2-amino-4-[(3-amino-4-hydroxyphenyl)methyl]phenol Chemical compound C1=C(O)C(N)=CC(CC=2C=C(N)C(O)=CC=2)=C1 KCFVSHSJPIVGCG-UHFFFAOYSA-N 0.000 description 1
- QHAHSDNQGXMQRI-UHFFFAOYSA-N 2-amino-4-[1-(3-amino-4-hydroxyphenyl)-1-phenylethyl]phenol Chemical compound C=1C=C(O)C(N)=CC=1C(C=1C=C(N)C(O)=CC=1)(C)C1=CC=CC=C1 QHAHSDNQGXMQRI-UHFFFAOYSA-N 0.000 description 1
- KGRCUVXWCDKABN-UHFFFAOYSA-N 2-amino-4-[1-(3-amino-4-hydroxyphenyl)-2,2,2-trifluoro-1-phenylethyl]phenol Chemical compound C1=C(O)C(N)=CC(C(C=2C=CC=CC=2)(C=2C=C(N)C(O)=CC=2)C(F)(F)F)=C1 KGRCUVXWCDKABN-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
- UKLPHTBVFJDWQM-UHFFFAOYSA-N 2-amino-4-[2-(3-amino-4-hydroxyphenyl)-1,1,1-trifluoropropan-2-yl]phenol Chemical compound C=1C=C(O)C(N)=CC=1C(C(F)(F)F)(C)C1=CC=C(O)C(N)=C1 UKLPHTBVFJDWQM-UHFFFAOYSA-N 0.000 description 1
- UHIDYCYNRPVZCK-UHFFFAOYSA-N 2-amino-4-[2-(3-amino-4-hydroxyphenyl)propan-2-yl]phenol Chemical compound C=1C=C(O)C(N)=CC=1C(C)(C)C1=CC=C(O)C(N)=C1 UHIDYCYNRPVZCK-UHFFFAOYSA-N 0.000 description 1
- ZGDMDBHLKNQPSD-UHFFFAOYSA-N 2-amino-5-(4-amino-3-hydroxyphenyl)phenol Chemical group C1=C(O)C(N)=CC=C1C1=CC=C(N)C(O)=C1 ZGDMDBHLKNQPSD-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
- DPYROBMRMXHROQ-UHFFFAOYSA-N 4,6-diaminobenzene-1,3-diol Chemical compound NC1=CC(N)=C(O)C=C1O DPYROBMRMXHROQ-UHFFFAOYSA-N 0.000 description 1
- AXBVYKSPLWLLPG-UHFFFAOYSA-N 4-(4-carbonochloridoyl-2,3,5-trifluorophenyl)-2,3,6-trifluoro-5-propan-2-ylidenecyclohexa-1,3-diene-1-carbonyl chloride Chemical compound CC(C)=C1C(F)C(C(Cl)=O)=C(F)C(F)=C1C1=CC(F)=C(C(Cl)=O)C(F)=C1F AXBVYKSPLWLLPG-UHFFFAOYSA-N 0.000 description 1
- LFEWXDOYPCWFHR-UHFFFAOYSA-N 4-(4-carboxybenzoyl)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C(=O)C1=CC=C(C(O)=O)C=C1 LFEWXDOYPCWFHR-UHFFFAOYSA-N 0.000 description 1
- VTDMBRAUHKUOON-UHFFFAOYSA-N 4-[(4-carboxyphenyl)methyl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1CC1=CC=C(C(O)=O)C=C1 VTDMBRAUHKUOON-UHFFFAOYSA-N 0.000 description 1
- 239000004642 Polyimide Substances 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- AEWGGPYHSLODJJ-UHFFFAOYSA-N bis(3-amino-4-hydroxyphenyl)methanone Chemical compound C1=C(O)C(N)=CC(C(=O)C=2C=C(N)C(O)=CC=2)=C1 AEWGGPYHSLODJJ-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 235000011089 carbon dioxide Nutrition 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
- RBHJBMIOOPYDBQ-UHFFFAOYSA-N carbon dioxide;propan-2-one Chemical compound O=C=O.CC(C)=O RBHJBMIOOPYDBQ-UHFFFAOYSA-N 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- 239000012024 dehydrating agents Substances 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- 238000000578 dry spinning Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 238000002074 melt spinning Methods 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- SGFZGUPEVMQHJJ-UHFFFAOYSA-N n-trimethylsilyl-5-[2-[3-(trimethylsilylamino)-4-trimethylsilyloxyphenyl]propan-2-yl]-2-trimethylsilyloxyaniline Chemical compound C=1C=C(O[Si](C)(C)C)C(N[Si](C)(C)C)=CC=1C(C)(C)C1=CC=C(O[Si](C)(C)C)C(N[Si](C)(C)C)=C1 SGFZGUPEVMQHJJ-UHFFFAOYSA-N 0.000 description 1
- MQGJVRLGBLAEMX-UHFFFAOYSA-N naphthalene-1,6-dicarbonyl chloride Chemical compound ClC(=O)C1=CC=CC2=CC(C(=O)Cl)=CC=C21 MQGJVRLGBLAEMX-UHFFFAOYSA-N 0.000 description 1
- RXOHFPCZGPKIRD-UHFFFAOYSA-N naphthalene-2,6-dicarboxylic acid Chemical compound C1=C(C(O)=O)C=CC2=CC(C(=O)O)=CC=C21 RXOHFPCZGPKIRD-UHFFFAOYSA-N 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 238000005504 petroleum refining Methods 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920002492 poly(sulfone) Polymers 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 238000002166 wet spinning 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (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)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62316014A JPH01159024A (ja) | 1987-12-16 | 1987-12-16 | 気体分離膜 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE3842093A1 true DE3842093A1 (de) | 1989-06-29 |
Family
ID=18072290
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE3842093A Withdrawn DE3842093A1 (de) | 1987-12-16 | 1988-12-14 | Semipermeable membran aus polybenzoxazol zur trennung von gasen |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JPH01159024A (enExample) |
| DE (1) | DE3842093A1 (enExample) |
| FR (1) | FR2624756A1 (enExample) |
| GB (1) | GB2211193B (enExample) |
| IT (1) | IT1228033B (enExample) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5034026A (en) * | 1990-04-20 | 1991-07-23 | The Dow Chemical Company | Polybenzazole polymers containing indan moieties |
| EP0525113A4 (en) * | 1990-04-20 | 1993-04-21 | The Dow Chemical Company | Porous polybenzoxazole and polybenzothiazole membranes |
| US5837032A (en) * | 1991-01-30 | 1998-11-17 | The Cynara Company | Gas separations utilizing glassy polymer membranes at sub-ambient temperatures |
| US5352272A (en) * | 1991-01-30 | 1994-10-04 | The Dow Chemical Company | Gas separations utilizing glassy polymer membranes at sub-ambient temperatures |
| JP3247953B2 (ja) * | 1992-09-30 | 2002-01-21 | 独立行政法人産業技術総合研究所 | 含水ゲル状気体分離膜 |
| US7465782B2 (en) * | 2005-07-13 | 2008-12-16 | E.I Du Pont De Nemours & Company | Method for making polybenzobisoxazole containing fiber |
| KR100932765B1 (ko) | 2008-02-28 | 2009-12-21 | 한양대학교 산학협력단 | 폴리이미드-폴리벤조옥사졸 공중합체, 이의 제조방법, 및이를 포함하는 기체 분리막 |
| KR100966176B1 (ko) * | 2008-03-12 | 2010-06-25 | 한양대학교 산학협력단 | 열전환 반응을 이용한 벤조옥사졸계 고분자의 제조방법, 이로써 얻어진 벤조옥사졸계 고분자, 및 이를 포함하는 기체 분리막 |
| US8083834B2 (en) * | 2008-05-07 | 2011-12-27 | Uop Llc | High permeability membrane operated at elevated temperature for upgrading natural gas |
| CN102099513B (zh) * | 2008-05-19 | 2012-12-12 | 汉阳大学校产学协力团 | 中空纤维、用于形成中空纤维的掺杂溶液组合物和使用所述掺杂溶液组合物制备中空纤维的方法 |
| WO2009142434A2 (ko) * | 2008-05-19 | 2009-11-26 | 한양대학교 산학협력단 | 중공사, 중공사 형성용 도프 용액 조성물 및 이를 이용한 중공사의 제조방법 |
| US8536299B2 (en) * | 2008-12-08 | 2013-09-17 | University Of Dayton | Rigid-rod copolymer compositions and the polymeric fibers fabricated from those compositions for enhanced flame resistance |
| US8127937B2 (en) * | 2009-03-27 | 2012-03-06 | Uop Llc | High performance cross-linked polybenzoxazole and polybenzothiazole polymer membranes |
| 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 |
| US8132678B2 (en) * | 2009-03-27 | 2012-03-13 | Uop Llc | Polybenzoxazole polymer-based mixed matrix membranes |
| US8613362B2 (en) * | 2009-03-27 | 2013-12-24 | Uop Llc | Polymer membranes derived from aromatic polyimide membranes |
| US8132677B2 (en) * | 2009-03-27 | 2012-03-13 | Uop Llc | Polymer membranes prepared from aromatic polyimide membranes by thermal treating and UV crosslinking |
| US8127936B2 (en) * | 2009-03-27 | 2012-03-06 | Uop Llc | High performance cross-linked polybenzoxazole and polybenzothiazole polymer membranes |
| US8459469B2 (en) | 2009-06-25 | 2013-06-11 | Uop Llc | Polybenzoxazole membranes prepared from aromatic polyamide membranes |
| US7810652B2 (en) * | 2009-09-25 | 2010-10-12 | Uop Llc | Method to improve the selectivity of polybenzoxazole membranes |
| WO2013111732A1 (ja) * | 2012-01-24 | 2013-08-01 | 公益財団法人名古屋産業科学研究所 | 気体分離膜 |
| JP6037804B2 (ja) | 2012-12-03 | 2016-12-07 | 富士フイルム株式会社 | ガス分離膜 |
| CN115970522A (zh) * | 2022-08-18 | 2023-04-18 | 齐齐哈尔大学 | 一种硅烷化热重排聚苯并恶唑气体分离膜材料的制备方法 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1059474A (en) * | 1963-06-14 | 1967-02-22 | Toyo Rayon Co Ltd | Polybenzoxazoles and process for their preparation |
| US3332907A (en) * | 1963-06-17 | 1967-07-25 | Du Pont | Oxy aromatic polyamides and process for preparation |
| US3306876A (en) * | 1965-02-09 | 1967-02-28 | Gen Electric | Heat-fusible polybenzoxazoles |
| DE1595723A1 (de) * | 1965-02-09 | 1970-04-30 | Gen Electric | Verfahren zur Herstellung von stickstoffhaltigen Polymeren |
| FR2193634A1 (en) * | 1972-07-20 | 1974-02-22 | Du Pont | Polyimide semi-permeable membranes |
| GB1499608A (en) * | 1976-11-01 | 1978-02-01 | Korshak V | Polybenzoxazoles |
| JPS5715819A (en) * | 1980-07-01 | 1982-01-27 | Ube Ind Ltd | Gas separating material |
| GB2188936B (en) * | 1986-03-06 | 1988-12-21 | Central Glass Co Ltd | Aromatic polyamides and polybenoxazoles having diphenylhexafluoropropane units |
| JPS62226987A (ja) * | 1986-03-27 | 1987-10-05 | Central Glass Co Ltd | 芳香族ジアミンおよびその製造法 |
| GB2191496A (en) * | 1986-05-30 | 1987-12-16 | Central Glass Co Ltd | Method of preparing aromatic polyamides and polybenzoxazoles |
-
1987
- 1987-12-16 JP JP62316014A patent/JPH01159024A/ja active Granted
-
1988
- 1988-12-14 DE DE3842093A patent/DE3842093A1/de not_active Withdrawn
- 1988-12-14 GB GB8829152A patent/GB2211193B/en not_active Expired - Fee Related
- 1988-12-15 FR FR8816565A patent/FR2624756A1/fr active Pending
- 1988-12-16 IT IT8822960A patent/IT1228033B/it active
Non-Patent Citations (1)
| Title |
|---|
| Macromolecules, Vol. 10, No. 5, 1977, 881-888 * |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2624756A1 (fr) | 1989-06-23 |
| JPH01159024A (ja) | 1989-06-22 |
| IT1228033B (it) | 1991-05-27 |
| GB2211193B (en) | 1990-12-19 |
| JPH0477610B2 (enExample) | 1992-12-08 |
| GB8829152D0 (en) | 1989-01-25 |
| IT8822960A0 (it) | 1988-12-16 |
| GB2211193A (en) | 1989-06-28 |
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| OP8 | Request for examination as to paragraph 44 patent law | ||
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