JP5746150B2 - 気体分離膜 - Google Patents
気体分離膜 Download PDFInfo
- Publication number
- JP5746150B2 JP5746150B2 JP2012510660A JP2012510660A JP5746150B2 JP 5746150 B2 JP5746150 B2 JP 5746150B2 JP 2012510660 A JP2012510660 A JP 2012510660A JP 2012510660 A JP2012510660 A JP 2012510660A JP 5746150 B2 JP5746150 B2 JP 5746150B2
- Authority
- JP
- Japan
- Prior art keywords
- gas separation
- separation membrane
- aromatic
- linear
- polyimide
- 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.)
- Expired - Fee Related
Links
- 238000000926 separation method Methods 0.000 title claims description 72
- 239000012528 membrane Substances 0.000 title claims description 56
- 229920005575 poly(amic acid) Polymers 0.000 claims description 68
- 229920001721 polyimide Polymers 0.000 claims description 51
- 239000004642 Polyimide Substances 0.000 claims description 47
- 125000003118 aryl group Chemical group 0.000 claims description 42
- -1 alkoxy compound Chemical class 0.000 claims description 22
- 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 21
- 238000006243 chemical reaction Methods 0.000 claims description 20
- 125000006158 tetracarboxylic acid group Chemical group 0.000 claims description 19
- 229920002959 polymer blend Polymers 0.000 claims description 17
- 150000004703 alkoxides Chemical class 0.000 claims description 16
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 14
- 125000003545 alkoxy group Chemical group 0.000 claims description 13
- 125000003277 amino group Chemical group 0.000 claims description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
- 229910052710 silicon Inorganic materials 0.000 claims description 10
- 229910052719 titanium Inorganic materials 0.000 claims description 10
- 239000010936 titanium Substances 0.000 claims description 10
- 229910052782 aluminium Inorganic materials 0.000 claims description 9
- 229910052749 magnesium Inorganic materials 0.000 claims description 9
- 239000011777 magnesium Substances 0.000 claims description 9
- 229910052726 zirconium Inorganic materials 0.000 claims description 9
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 8
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 7
- 229920000592 inorganic polymer Polymers 0.000 claims description 7
- 239000010703 silicon Substances 0.000 claims description 7
- 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 claims description 6
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 6
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 6
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 claims description 6
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 6
- 150000004985 diamines Chemical class 0.000 claims description 5
- NLGOBIIKXFNGQR-UHFFFAOYSA-N 2-amino-4-[9-(3-amino-4-hydroxyphenyl)fluoren-9-yl]phenol Chemical compound C1=C(O)C(N)=CC(C2(C3=CC=CC=C3C3=CC=CC=C32)C=2C=C(N)C(O)=CC=2)=C1 NLGOBIIKXFNGQR-UHFFFAOYSA-N 0.000 claims description 4
- 239000007795 chemical reaction product Substances 0.000 claims description 3
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- 238000005470 impregnation Methods 0.000 claims 1
- 239000007789 gas Substances 0.000 description 68
- 239000000243 solution Substances 0.000 description 27
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 24
- 239000002253 acid Substances 0.000 description 24
- 230000035699 permeability Effects 0.000 description 24
- 239000000377 silicon dioxide Substances 0.000 description 14
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 13
- 229920000642 polymer Polymers 0.000 description 13
- 239000011259 mixed solution Substances 0.000 description 10
- 229910052809 inorganic oxide Inorganic materials 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- LFQCEHFDDXELDD-UHFFFAOYSA-N tetramethyl orthosilicate Chemical compound CO[Si](OC)(OC)OC LFQCEHFDDXELDD-UHFFFAOYSA-N 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- 150000004984 aromatic diamines Chemical class 0.000 description 6
- 239000002243 precursor Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 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 5
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 5
- 150000001491 aromatic compounds Chemical class 0.000 description 5
- 125000004429 atom Chemical group 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- BFXIKLCIZHOAAZ-UHFFFAOYSA-N methyltrimethoxysilane Chemical compound CO[Si](C)(OC)OC BFXIKLCIZHOAAZ-UHFFFAOYSA-N 0.000 description 5
- 239000012299 nitrogen atmosphere Substances 0.000 description 5
- 229920000728 polyester Polymers 0.000 description 5
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 239000001110 calcium chloride Substances 0.000 description 4
- 229910001628 calcium chloride Inorganic materials 0.000 description 4
- 239000001569 carbon dioxide Substances 0.000 description 4
- 229910002092 carbon dioxide Inorganic materials 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 229920006254 polymer film Polymers 0.000 description 4
- 229920005597 polymer membrane Polymers 0.000 description 4
- 150000003457 sulfones Chemical class 0.000 description 4
- 230000002194 synthesizing effect Effects 0.000 description 4
- MXPYJVUYLVNEBB-UHFFFAOYSA-N 2-[2-(2-carboxybenzoyl)oxycarbonylbenzoyl]oxycarbonylbenzoic acid Chemical compound OC(=O)C1=CC=CC=C1C(=O)OC(=O)C1=CC=CC=C1C(=O)OC(=O)C1=CC=CC=C1C(O)=O MXPYJVUYLVNEBB-UHFFFAOYSA-N 0.000 description 3
- JCRRFJIVUPSNTA-UHFFFAOYSA-N 4-[4-(4-aminophenoxy)phenoxy]aniline Chemical compound C1=CC(N)=CC=C1OC(C=C1)=CC=C1OC1=CC=C(N)C=C1 JCRRFJIVUPSNTA-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 150000002430 hydrocarbons Chemical group 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 238000006068 polycondensation reaction Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- 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 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- 125000004018 acid anhydride group Chemical group 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 238000005266 casting Methods 0.000 description 2
- 239000002131 composite material Substances 0.000 description 2
- 230000007423 decrease Effects 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
- 239000011521 glass Substances 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 239000012510 hollow fiber Substances 0.000 description 2
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 229910052814 silicon oxide Inorganic materials 0.000 description 2
- FHBXQJDYHHJCIF-UHFFFAOYSA-N (2,3-diaminophenyl)-phenylmethanone Chemical compound NC1=CC=CC(C(=O)C=2C=CC=CC=2)=C1N FHBXQJDYHHJCIF-UHFFFAOYSA-N 0.000 description 1
- YLIKHLYLPLTUTL-UHFFFAOYSA-N (3-aminophenyl)-(2,4-diaminophenyl)methanone Chemical compound NC1=C(C(=O)C2=CC(=CC=C2)N)C=CC(=C1)N YLIKHLYLPLTUTL-UHFFFAOYSA-N 0.000 description 1
- IGUXFXNMXMXLCK-UHFFFAOYSA-N (3-aminophenyl)-(3,4-diaminophenyl)methanone Chemical compound NC1=CC=CC(C(=O)C=2C=C(N)C(N)=CC=2)=C1 IGUXFXNMXMXLCK-UHFFFAOYSA-N 0.000 description 1
- PGHVMIHPOANRPS-UHFFFAOYSA-N (3-aminophenyl)-(3,5-diaminophenyl)methanone Chemical compound NC1=CC=CC(C(=O)C=2C=C(N)C=C(N)C=2)=C1 PGHVMIHPOANRPS-UHFFFAOYSA-N 0.000 description 1
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 1
- NPSMSOMZCHVSSW-UHFFFAOYSA-N (4-aminophenyl)-(2,4-diaminophenyl)methanone Chemical compound C1=CC(N)=CC=C1C(=O)C1=CC=C(N)C=C1N NPSMSOMZCHVSSW-UHFFFAOYSA-N 0.000 description 1
- JPMLZYOQEMXUTO-UHFFFAOYSA-N (ethoxy-methyl-pentan-2-yloxysilyl)formic acid Chemical compound C(CC)C(C)O[Si](OCC)(C(=O)O)C JPMLZYOQEMXUTO-UHFFFAOYSA-N 0.000 description 1
- 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
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 1
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- CWFXFZKQVWETGV-UHFFFAOYSA-N 2-[3,5-bis(2-aminophenoxy)phenoxy]aniline Chemical compound NC1=CC=CC=C1OC1=CC(OC=2C(=CC=CC=2)N)=CC(OC=2C(=CC=CC=2)N)=C1 CWFXFZKQVWETGV-UHFFFAOYSA-N 0.000 description 1
- QDMXRSFKPPVBDW-UHFFFAOYSA-N 2-[9-(2-aminophenyl)fluoren-9-yl]aniline Chemical compound NC1=CC=CC=C1C1(C=2C(=CC=CC=2)N)C2=CC=CC=C2C2=CC=CC=C21 QDMXRSFKPPVBDW-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
- NHIVDJVBQZKDFC-UHFFFAOYSA-N 2-amino-5-(3-amino-4-hydroxyphenyl)phenol Chemical group C1=C(O)C(N)=CC=C1C1=CC=C(O)C(N)=C1 NHIVDJVBQZKDFC-UHFFFAOYSA-N 0.000 description 1
- RCYNJDVUURMJOZ-UHFFFAOYSA-N 2-amino-5-[(4-amino-3-hydroxyphenyl)methyl]phenol Chemical compound C1=C(O)C(N)=CC=C1CC1=CC=C(N)C(O)=C1 RCYNJDVUURMJOZ-UHFFFAOYSA-N 0.000 description 1
- BORGTKLSMLPLHK-UHFFFAOYSA-N 2-amino-5-[1-(4-amino-3-hydroxyphenyl)ethyl]phenol Chemical compound C=1C=C(N)C(O)=CC=1C(C)C1=CC=C(N)C(O)=C1 BORGTKLSMLPLHK-UHFFFAOYSA-N 0.000 description 1
- JDFAWEKPFLGRAK-UHFFFAOYSA-N 2-amino-5-[2-(4-amino-3-hydroxyphenyl)propan-2-yl]phenol Chemical compound C=1C=C(N)C(O)=CC=1C(C)(C)C1=CC=C(N)C(O)=C1 JDFAWEKPFLGRAK-UHFFFAOYSA-N 0.000 description 1
- ISPYQTSUDJAMAB-UHFFFAOYSA-N 2-chlorophenol Chemical compound OC1=CC=CC=C1Cl ISPYQTSUDJAMAB-UHFFFAOYSA-N 0.000 description 1
- JQCLDNFNUWSZSH-UHFFFAOYSA-N 2-methoxysilyl-3,4-dimethylbenzoic acid Chemical compound CC1=C(C(=C(C(=O)O)C=C1)[SiH2]OC)C JQCLDNFNUWSZSH-UHFFFAOYSA-N 0.000 description 1
- HSTOKWSFWGCZMH-UHFFFAOYSA-N 3,3'-diaminobenzidine Chemical compound C1=C(N)C(N)=CC=C1C1=CC=C(N)C(N)=C1 HSTOKWSFWGCZMH-UHFFFAOYSA-N 0.000 description 1
- YHMDIRXBIAWCFD-UHFFFAOYSA-N 3-(2-propylphenoxy)phthalic acid Chemical compound CCCC1=CC=CC=C1OC1=CC=CC(C(O)=O)=C1C(O)=O YHMDIRXBIAWCFD-UHFFFAOYSA-N 0.000 description 1
- GXDMUOPCQNLBCZ-UHFFFAOYSA-N 3-(3-triethoxysilylpropyl)oxolane-2,5-dione Chemical compound CCO[Si](OCC)(OCC)CCCC1CC(=O)OC1=O GXDMUOPCQNLBCZ-UHFFFAOYSA-N 0.000 description 1
- UWRKLSNNNKRXSF-UHFFFAOYSA-N 3-[2,3-bis(3-aminophenyl)phenyl]aniline Chemical compound NC1=CC=CC(C=2C(=C(C=3C=C(N)C=CC=3)C=CC=2)C=2C=C(N)C=CC=2)=C1 UWRKLSNNNKRXSF-UHFFFAOYSA-N 0.000 description 1
- JHYZHLNKNMVBSP-UHFFFAOYSA-N 3-[3,5-bis(3-aminophenoxy)phenoxy]aniline Chemical compound NC1=CC=CC(OC=2C=C(OC=3C=C(N)C=CC=3)C=C(OC=3C=C(N)C=CC=3)C=2)=C1 JHYZHLNKNMVBSP-UHFFFAOYSA-N 0.000 description 1
- GPXCORHXFPYJEH-UHFFFAOYSA-N 3-[[3-aminopropyl(dimethyl)silyl]oxy-dimethylsilyl]propan-1-amine Chemical compound NCCC[Si](C)(C)O[Si](C)(C)CCCN GPXCORHXFPYJEH-UHFFFAOYSA-N 0.000 description 1
- HXLAEGYMDGUSBD-UHFFFAOYSA-N 3-[diethoxy(methyl)silyl]propan-1-amine Chemical compound CCO[Si](C)(OCC)CCCN HXLAEGYMDGUSBD-UHFFFAOYSA-N 0.000 description 1
- JLIMOJXOVUKDJX-UHFFFAOYSA-N 3-[methoxy(dimethyl)silyl]aniline Chemical compound CO[Si](C)(C)C1=CC=CC(N)=C1 JLIMOJXOVUKDJX-UHFFFAOYSA-N 0.000 description 1
- HORNXRXVQWOLPJ-UHFFFAOYSA-N 3-chlorophenol Chemical compound OC1=CC=CC(Cl)=C1 HORNXRXVQWOLPJ-UHFFFAOYSA-N 0.000 description 1
- SJECZPVISLOESU-UHFFFAOYSA-N 3-trimethoxysilylpropan-1-amine Chemical compound CO[Si](OC)(OC)CCCN SJECZPVISLOESU-UHFFFAOYSA-N 0.000 description 1
- XTEBLARUAVEBRF-UHFFFAOYSA-N 4-(1,1,1,3,3,3-hexafluoropropan-2-yl)aniline Chemical compound NC1=CC=C(C(C(F)(F)F)C(F)(F)F)C=C1 XTEBLARUAVEBRF-UHFFFAOYSA-N 0.000 description 1
- JKETWUADWJKEKN-UHFFFAOYSA-N 4-(3,4-diaminophenyl)sulfonylbenzene-1,2-diamine Chemical compound C1=C(N)C(N)=CC=C1S(=O)(=O)C1=CC=C(N)C(N)=C1 JKETWUADWJKEKN-UHFFFAOYSA-N 0.000 description 1
- HOSGAMZDLWSREP-UHFFFAOYSA-N 4-(3-aminophenyl)benzene-1,2-diamine Chemical group NC1=CC=CC(C=2C=C(N)C(N)=CC=2)=C1 HOSGAMZDLWSREP-UHFFFAOYSA-N 0.000 description 1
- KDSSYYNSKCBPGC-UHFFFAOYSA-N 4-(3-aminophenyl)benzene-1,3-diamine Chemical group NC1=CC(N)=CC=C1C1=CC=CC(N)=C1 KDSSYYNSKCBPGC-UHFFFAOYSA-N 0.000 description 1
- MPKIJEUTPZPJFP-UHFFFAOYSA-N 4-(4-aminophenoxy)benzene-1,2-diamine Chemical compound C1=CC(N)=CC=C1OC1=CC=C(N)C(N)=C1 MPKIJEUTPZPJFP-UHFFFAOYSA-N 0.000 description 1
- RVYIVHUVZXDTGN-UHFFFAOYSA-N 4-(4-aminophenyl)benzene-1,2-diamine Chemical group C1=CC(N)=CC=C1C1=CC=C(N)C(N)=C1 RVYIVHUVZXDTGN-UHFFFAOYSA-N 0.000 description 1
- GMJHZZCVWDJKFB-UHFFFAOYSA-N 4-(4-aminophenyl)benzene-1,3-diamine Chemical group C1=CC(N)=CC=C1C1=CC=C(N)C=C1N GMJHZZCVWDJKFB-UHFFFAOYSA-N 0.000 description 1
- AUTXJLFNORABNE-UHFFFAOYSA-N 4-(4-aminophenyl)sulfanylbenzene-1,2-diamine Chemical compound C1=CC(N)=CC=C1SC1=CC=C(N)C(N)=C1 AUTXJLFNORABNE-UHFFFAOYSA-N 0.000 description 1
- LMCLQTHHLNHUPN-UHFFFAOYSA-N 4-(4-aminophenyl)sulfonylbenzene-1,2-diamine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C(N)=C1 LMCLQTHHLNHUPN-UHFFFAOYSA-N 0.000 description 1
- HLBLWEWZXPIGSM-UHFFFAOYSA-N 4-Aminophenyl ether Chemical compound C1=CC(N)=CC=C1OC1=CC=C(N)C=C1 HLBLWEWZXPIGSM-UHFFFAOYSA-N 0.000 description 1
- SYBFZFROLBNDDF-UHFFFAOYSA-N 4-[2,3-bis(4-aminophenyl)phenyl]aniline Chemical compound C1=CC(N)=CC=C1C1=CC=CC(C=2C=CC(N)=CC=2)=C1C1=CC=C(N)C=C1 SYBFZFROLBNDDF-UHFFFAOYSA-N 0.000 description 1
- RVIDWCHHVDGTMP-UHFFFAOYSA-N 4-[2-(3-aminophenyl)-1,1,1,3,3,3-hexafluoropropan-2-yl]benzene-1,2-diamine Chemical compound NC=1C=C(C=CC1N)C(C(F)(F)F)(C(F)(F)F)C1=CC(=CC=C1)N RVIDWCHHVDGTMP-UHFFFAOYSA-N 0.000 description 1
- LTNHKXMJAOIVIX-UHFFFAOYSA-N 4-[2-(3-aminophenyl)propan-2-yl]benzene-1,2-diamine Chemical compound NC=1C=C(C=CC1N)C(C)(C)C1=CC(=CC=C1)N LTNHKXMJAOIVIX-UHFFFAOYSA-N 0.000 description 1
- RYYUUQPLFHRZOY-UHFFFAOYSA-N 4-[2-(4-aminophenoxy)phenoxy]aniline Chemical compound C1=CC(N)=CC=C1OC1=CC=CC=C1OC1=CC=C(N)C=C1 RYYUUQPLFHRZOY-UHFFFAOYSA-N 0.000 description 1
- GBOYBJSUOVZGSB-UHFFFAOYSA-N 4-[2-(4-aminophenyl)-1,1,1,3,3,3-hexafluoropropan-2-yl]benzene-1,2-diamine Chemical compound NC1=C(N)C=C(C(C(F)(F)F)(C2=CC=C(N)C=C2)C(F)(F)F)C=C1 GBOYBJSUOVZGSB-UHFFFAOYSA-N 0.000 description 1
- XGOVGCHNHXMWEH-UHFFFAOYSA-N 4-[2-(4-aminophenyl)-1,1,1,3,3,3-hexafluoropropan-2-yl]benzene-1,3-diamine Chemical compound NC1=CC(N)=C(C(C(F)(F)F)(C2=CC=C(N)C=C2)C(F)(F)F)C=C1 XGOVGCHNHXMWEH-UHFFFAOYSA-N 0.000 description 1
- LWKJREOYDSVPDF-UHFFFAOYSA-N 4-[2-(4-aminophenyl)propan-2-yl]benzene-1,2-diamine Chemical compound NC1=C(N)C=C(C(C)(C2=CC=C(N)C=C2)C)C=C1 LWKJREOYDSVPDF-UHFFFAOYSA-N 0.000 description 1
- BETSGYKQTIDAQB-UHFFFAOYSA-N 4-[2-(4-aminophenyl)propan-2-yl]benzene-1,3-diamine Chemical compound CC(C1=CC=C(N)C=C1N)(C)C1=CC=C(N)C=C1 BETSGYKQTIDAQB-UHFFFAOYSA-N 0.000 description 1
- YPGXCJNQPKHBLH-UHFFFAOYSA-N 4-[2-[2-[2-(4-aminophenoxy)phenyl]-1,1,1,3,3,3-hexafluoropropan-2-yl]phenoxy]aniline Chemical compound C1=CC(N)=CC=C1OC1=CC=CC=C1C(C(F)(F)F)(C(F)(F)F)C1=CC=CC=C1OC1=CC=C(N)C=C1 YPGXCJNQPKHBLH-UHFFFAOYSA-N 0.000 description 1
- AJYDKROUZBIMLE-UHFFFAOYSA-N 4-[2-[2-[2-(4-aminophenoxy)phenyl]propan-2-yl]phenoxy]aniline Chemical compound C=1C=CC=C(OC=2C=CC(N)=CC=2)C=1C(C)(C)C1=CC=CC=C1OC1=CC=C(N)C=C1 AJYDKROUZBIMLE-UHFFFAOYSA-N 0.000 description 1
- UTDAGHZGKXPRQI-UHFFFAOYSA-N 4-[4-[4-(4-aminophenoxy)phenyl]sulfonylphenoxy]aniline Chemical compound C1=CC(N)=CC=C1OC1=CC=C(S(=O)(=O)C=2C=CC(OC=3C=CC(N)=CC=3)=CC=2)C=C1 UTDAGHZGKXPRQI-UHFFFAOYSA-N 0.000 description 1
- GBHRFRGWXUDXOE-UHFFFAOYSA-N 4-[[1,3-bis(4-aminophenoxy)-2,4-dihydrotriazin-5-yl]oxy]aniline Chemical compound C1=CC(N)=CC=C1ON1NN(OC=2C=CC(N)=CC=2)C=C(OC=2C=CC(N)=CC=2)C1 GBHRFRGWXUDXOE-UHFFFAOYSA-N 0.000 description 1
- SNLFYGIUTYKKOE-UHFFFAOYSA-N 4-n,4-n-bis(4-aminophenyl)benzene-1,4-diamine Chemical compound C1=CC(N)=CC=C1N(C=1C=CC(N)=CC=1)C1=CC=C(N)C=C1 SNLFYGIUTYKKOE-UHFFFAOYSA-N 0.000 description 1
- CNODSORTHKVDEM-UHFFFAOYSA-N 4-trimethoxysilylaniline Chemical compound CO[Si](OC)(OC)C1=CC=C(N)C=C1 CNODSORTHKVDEM-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
- FKEFNFCYNXARPG-UHFFFAOYSA-N 5-(3-aminophenyl)benzene-1,3-diamine Chemical group NC1=CC=CC(C=2C=C(N)C=C(N)C=2)=C1 FKEFNFCYNXARPG-UHFFFAOYSA-N 0.000 description 1
- ZVBBGWMHPIVCDQ-UHFFFAOYSA-N 5-(4-aminophenyl)benzene-1,3-diamine Chemical group C1=CC(N)=CC=C1C1=CC(N)=CC(N)=C1 ZVBBGWMHPIVCDQ-UHFFFAOYSA-N 0.000 description 1
- JEGPYJCAPBYKCM-UHFFFAOYSA-N 5-[2,3-bis(3,5-diaminophenoxy)phenoxy]benzene-1,3-diamine Chemical compound NC1=CC(N)=CC(OC=2C(=C(OC=3C=C(N)C=C(N)C=3)C=CC=2)OC=2C=C(N)C=C(N)C=2)=C1 JEGPYJCAPBYKCM-UHFFFAOYSA-N 0.000 description 1
- CLMCBAHAKWATHO-UHFFFAOYSA-N 5-[2,3-bis(3,5-diaminophenyl)phenyl]benzene-1,3-diamine Chemical compound NC1=CC(N)=CC(C=2C(=C(C=3C=C(N)C=C(N)C=3)C=CC=2)C=2C=C(N)C=C(N)C=2)=C1 CLMCBAHAKWATHO-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- HVZQORSFCXMXQQ-UHFFFAOYSA-N NC1=C(C=CC(=C1)N)C(C(F)(F)F)(C(F)(F)F)C1=CC(=CC=C1)N Chemical compound NC1=C(C=CC(=C1)N)C(C(F)(F)F)(C(F)(F)F)C1=CC(=CC=C1)N HVZQORSFCXMXQQ-UHFFFAOYSA-N 0.000 description 1
- UFMHSJDAUMVZJN-UHFFFAOYSA-N NC1=C(C=CC(=C1)N)C(C)(C)C1=CC(=CC=C1)N Chemical compound NC1=C(C=CC(=C1)N)C(C)(C)C1=CC(=CC=C1)N UFMHSJDAUMVZJN-UHFFFAOYSA-N 0.000 description 1
- PJNOQSFRMFLLKX-UHFFFAOYSA-N NC=1C=C(C(=O)C2=CC=C(C=C2)N)C=C(C1)N Chemical compound NC=1C=C(C(=O)C2=CC=C(C=C2)N)C=C(C1)N PJNOQSFRMFLLKX-UHFFFAOYSA-N 0.000 description 1
- XSABGUPFVXPSPR-UHFFFAOYSA-N NC=1C=C(C=C(C1)N)C(C(F)(F)F)(C(F)(F)F)C1=CC(=CC=C1)N Chemical compound NC=1C=C(C=C(C1)N)C(C(F)(F)F)(C(F)(F)F)C1=CC(=CC=C1)N XSABGUPFVXPSPR-UHFFFAOYSA-N 0.000 description 1
- FGYXWDZGUZCMBI-UHFFFAOYSA-N NC=1C=C(C=C(C1)N)C(C(F)(F)F)(C(F)(F)F)C1=CC=C(C=C1)N Chemical compound NC=1C=C(C=C(C1)N)C(C(F)(F)F)(C(F)(F)F)C1=CC=C(C=C1)N FGYXWDZGUZCMBI-UHFFFAOYSA-N 0.000 description 1
- FXVAHGPIWRSSJT-UHFFFAOYSA-N NC=1C=C(C=C(C1)N)C(C)(C)C1=CC(=CC=C1)N Chemical compound NC=1C=C(C=C(C1)N)C(C)(C)C1=CC(=CC=C1)N FXVAHGPIWRSSJT-UHFFFAOYSA-N 0.000 description 1
- XVWIOQNXGDUPOJ-UHFFFAOYSA-N NC=1C=C(C=C(C1)N)C(C)(C)C1=CC=C(C=C1)N Chemical compound NC=1C=C(C=C(C1)N)C(C)(C)C1=CC=C(C=C1)N XVWIOQNXGDUPOJ-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 229910004298 SiO 2 Inorganic materials 0.000 description 1
- BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical compound CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 description 1
- SAUFCSXDXOZOJB-UHFFFAOYSA-N [butoxy(dimethoxy)silyl]formic acid Chemical compound C(CC)CO[Si](OC)(OC)C(=O)O SAUFCSXDXOZOJB-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- SMZOGRDCAXLAAR-UHFFFAOYSA-N aluminium isopropoxide Chemical compound [Al+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] SMZOGRDCAXLAAR-UHFFFAOYSA-N 0.000 description 1
- JPUHCPXFQIXLMW-UHFFFAOYSA-N aluminium triethoxide Chemical compound CCO[Al](OCC)OCC JPUHCPXFQIXLMW-UHFFFAOYSA-N 0.000 description 1
- XIWMTQIUUWJNRP-UHFFFAOYSA-N amidol Chemical compound NC1=CC=C(O)C(N)=C1 XIWMTQIUUWJNRP-UHFFFAOYSA-N 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- RPHKINMPYFJSCF-UHFFFAOYSA-N benzene-1,3,5-triamine Chemical compound NC1=CC(N)=CC(N)=C1 RPHKINMPYFJSCF-UHFFFAOYSA-N 0.000 description 1
- QLRMWXKBIDRYEQ-UHFFFAOYSA-N bis(4-amino-3-hydroxyphenyl)methanone Chemical compound C1=C(O)C(N)=CC=C1C(=O)C1=CC=C(N)C(O)=C1 QLRMWXKBIDRYEQ-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000007416 differential thermogravimetric analysis Methods 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- ZZTCPWRAHWXWCH-UHFFFAOYSA-N diphenylmethanediamine Chemical compound C=1C=CC=CC=1C(N)(N)C1=CC=CC=C1 ZZTCPWRAHWXWCH-UHFFFAOYSA-N 0.000 description 1
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- XGZNHFPFJRZBBT-UHFFFAOYSA-N ethanol;titanium Chemical compound [Ti].CCO.CCO.CCO.CCO XGZNHFPFJRZBBT-UHFFFAOYSA-N 0.000 description 1
- UARGAUQGVANXCB-UHFFFAOYSA-N ethanol;zirconium Chemical compound [Zr].CCO.CCO.CCO.CCO UARGAUQGVANXCB-UHFFFAOYSA-N 0.000 description 1
- 239000004210 ether based solvent Substances 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- XDKQUSKHRIUJEO-UHFFFAOYSA-N magnesium;ethanolate Chemical compound [Mg+2].CC[O-].CC[O-] XDKQUSKHRIUJEO-UHFFFAOYSA-N 0.000 description 1
- CRGZYKWWYNQGEC-UHFFFAOYSA-N magnesium;methanolate Chemical compound [Mg+2].[O-]C.[O-]C CRGZYKWWYNQGEC-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- ZEIWWVGGEOHESL-UHFFFAOYSA-N methanol;titanium Chemical compound [Ti].OC.OC.OC.OC ZEIWWVGGEOHESL-UHFFFAOYSA-N 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- HBELKEREKFGFNM-UHFFFAOYSA-N n'-[[4-(2-trimethoxysilylethyl)phenyl]methyl]ethane-1,2-diamine Chemical compound CO[Si](OC)(OC)CCC1=CC=C(CNCCN)C=C1 HBELKEREKFGFNM-UHFFFAOYSA-N 0.000 description 1
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- SOQBVABWOPYFQZ-UHFFFAOYSA-N oxygen(2-);titanium(4+) Chemical group [O-2].[O-2].[Ti+4] SOQBVABWOPYFQZ-UHFFFAOYSA-N 0.000 description 1
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 238000007655 standard test method Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 description 1
- UAEJRRZPRZCUBE-UHFFFAOYSA-N trimethoxyalumane Chemical compound [Al+3].[O-]C.[O-]C.[O-]C UAEJRRZPRZCUBE-UHFFFAOYSA-N 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
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- 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
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D67/00—Processes specially adapted for manufacturing semi-permeable membranes for separation processes or apparatus
- B01D67/0039—Inorganic membrane manufacture
- B01D67/0048—Inorganic membrane manufacture by sol-gel transition
-
- 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
- B01D71/00—Semi-permeable membranes for separation processes or apparatus characterised by the material; Manufacturing processes specially adapted therefor
- B01D71/06—Organic material
- B01D71/70—Polymers having silicon in the main chain, with or without sulfur, nitrogen, oxygen or carbon only
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- 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
- C08G73/1003—Preparatory processes
- C08G73/1007—Preparatory processes from tetracarboxylic acids or derivatives and diamines
- C08G73/101—Preparatory processes from tetracarboxylic acids or derivatives and diamines containing chain terminating or branching agents
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- 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
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/42—Block-or graft-polymers containing polysiloxane sequences
- C08G77/452—Block-or graft-polymers containing polysiloxane sequences containing nitrogen-containing sequences
- C08G77/455—Block-or graft-polymers containing polysiloxane sequences containing nitrogen-containing sequences containing polyamide, polyesteramide or polyimide sequences
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- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D2325/00—Details relating to properties of membranes
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- General Chemical & Material Sciences (AREA)
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- Separation Using Semi-Permeable Membranes (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Silicon Polymers (AREA)
Description
R1 mM(OR2)n・・・式
R1 、R2 :炭化水素基
M:Si、Mg、Al、Zr又はTiの何れかの原子
m:0又は正の整数
n:正の整数
m+n:原子Mの原子価
R1 mM(OR2)n・・・式(1)
R1 、R2 :炭化水素基
M:Si、Mg、Al、Zr又はTiの何れかの原子
m:0又は正の整数
n:正の整数
m+n:原子Mの原子価
撹拌機、窒素導入管及び塩化カルシウム管を備えた300mLの三つ口フラスコに1,3,5−トリス(アミノフェノキシ)ベンゼン[TAPOB]:7.2g(18mmol)を仕込み、ジメチルアセトアミド(DMAc):30mLを加えて溶解した。この溶液を撹拌しながら、54mLのDMAcに溶解した4,4’−(ヘキサフルオロイソプロピリデン)ジフタル酸二無水物[6FDA]:6.4g(14.4mmol)を徐々に加えた後、25℃で3時間撹拌した。
撹拌機、窒素導入管及び塩化カルシウム管を備えた300mLの三つ口フラスコに6FDA:32.0g(72mmol)を仕込み、DMAc:156mLを加えて溶解した。この溶液を撹拌しながら、3,3’−ジヒドロキシベンジジン(HAB):15.3g(71.28mmol)を徐々に加え、25℃で3時間撹拌し、直鎖ヒドロキシポリアミド酸(6FDA−HAB)を合成した。尚、反応溶液のポリマー濃度は26.8重量%、回転粘度は100000cP以上であった。
撹拌機、窒素導入管及び塩化カルシウム管を備えた300mLの三つ口フラスコに6FDA:32.0g(72mmol)を仕込み、DMAc:141mLを加えて溶解した。この溶液を撹拌しながら、9,9−ビス(3−アミノ−4−ヒドロキシフェニル)フルオレン[BAHF]:13.6g(35.64mmol)、及び1,4−ビス(4−アミノフェノキシ)ベンゼン[TPEQ]:10.4g(35.64mmol)を徐々に加え、25℃で3時間撹拌し、直鎖ヒドロキシポリアミド酸II(6FDA−BAHF/TPEQ)を合成した。尚、反応溶液のポリマー濃度は28.4重量%、回転粘度は100000cP以上であった。
撹拌機、窒素導入管及び塩化カルシウム管を備えた300mLの三つ口フラスコに6FDA:32.0g(72mmol)を仕込み、DMAc:156mLを加えて溶解した。この溶液を撹拌しながら、1,4−ビス(4−アミノフェノキシ)ベンゼン[TPEQ]:20.8g(71.28mmol)を徐々に加え、25℃で3時間撹拌し、直鎖ポリアミド酸(6FDA−TPEQ)を合成した。尚、反応溶液のポリマー濃度は26.5重量%、回転粘度は100000cP以上であった。
4種類のポリアミド酸のDMAc溶液を、各ポリアミド酸がそれぞれ下記表1に示す組成となるような割合において、混合した。尚、得られた混合溶液の回転粘度を表1に示す。
多分岐ポリアミド酸、直鎖ヒドロキシポリアミド酸I、直鎖ポリアミド酸、及び直鎖ヒドロキシポリアミド酸IIの各DMAc溶液を、単独でポリエステルシート上にキャストし、85℃で2時間、乾燥した後に剥がし取り、更に窒素雰囲気下にて100℃で1時間、200℃で1時間、300℃で1時間、加熱処理を施すことにより、ポリイミドフィルムを得た。
多分岐ポリアミド酸のDMAc溶液及び直鎖ポリアミド酸のDMAc溶液を、多分岐ポリアミド酸:直鎖ポリアミド酸=33:67(重量比)の割合において混合した。この混合溶液のポリマー濃度は21.3重量%、回転粘度は8580cPであった。得られた混合溶液をポリエステルシート上にキャストし、85℃で2時間、乾燥した後に剥がし取り、更に窒素雰囲気下にて100℃で1時間、200℃で1時間、300℃で1時間、加熱処理を施すことにより、ポリイミドフィルムを得た。
比較例5で得られた混合溶液に、テトラメトキシシラン(TMOS)及びイオン交換水を適量加え、室温で24時間撹拌した。この溶液をポリエステルシート上にキャストし、85℃で2時間、乾燥した後に剥がし取り、更に窒素雰囲気下にて100℃で1時間、200℃で1時間、300℃で1時間、加熱処理を施すことにより、ポリイミド−シリカハイブリッドフィルムを得た。得られたポリイミド−シリカハイブリッドフィルムについてTG−DTA測定を行なったところ、シリカ換算で10重量%のシリカが含まれていた。
直鎖ヒドロキシポリアミド酸のDMAc溶液及び直鎖ポリアミド酸のDMAc溶液を、直鎖ヒドロキシポリアミド酸:直鎖ポリアミド酸=50:50(重量比)の割合において混合した。この混合溶液のポリマー濃度は24.8重量%、回転粘度は100000cP以上であった(表1)。得られた混合溶液をポリエステルシート上にキャストし、85℃で2時間、乾燥した後に剥がし取り、更に窒素雰囲気下にて100℃で1時間、200℃で1時間、300℃で1時間、加熱処理を施すことにより、ポリイミドフィルムを得た。
lnX=φAlnXA+φBlnXB+φClnXC+・・・
X:ポリマーブレンドの気体透過係数(理論値)又は気体分離係数(理論値)
φi :ポリマーiの体積分率
Xi :ポリマーiの気体透過係数又は気体分離係数
Claims (6)
- 直鎖ヒドロキシポリイミド及び多分岐ポリイミドを含むポリマーブレンドからなる気体分離膜。
- 前記直鎖ヒドロキシポリイミドが、芳香族テトラカルボン酸二無水物と、少なくとも芳香族ヒドロキシジアミンを含むジアミン成分とを反応せしめて得られるものである請求項1に記載の気体分離膜。
- 前記芳香族ヒドロキシジアミンが、3,3’−ジヒドロキシベンジジン又は9,9−ビス(3−アミノ−4−ヒドロキシフェニル)フルオレンである請求項1又は請求項2に記載の気体分離膜。
- 前記多分岐ポリイミドが、芳香族テトラカルボン酸二無水物と、芳香族トリアミンと、末端にアミノ基或いはカルボキシル基を有する、ケイ素、マグネシウム、アルミニウム、ジルコニウム又はチタンのアルコキシ化合物若しくはそれらの誘導体とを反応せしめて得られる、複数の末端のうちの少なくとも一部に水酸基又はアルコキシ基を有する多分岐ポリアミド酸を、イミド化せしめてなるものである請求項1〜請求項3の何れか1項に記載の気体分離膜。
- 前記多分岐ポリイミドが、芳香族テトラカルボン酸二無水物と、芳香族トリアミンと、末端にアミノ基或いはカルボキシル基を有する、ケイ素、マグネシウム、アルミニウム、ジルコニウム又はチタンのアルコキシ化合物若しくはそれらの誘導体とを反応せしめて得られる、複数の末端のうちの少なくとも一部に水酸基又はアルコキシ基を有する多分岐ポリアミド酸と、下記式で表わされるアルコキシドの少なくとも一種以上とを、水の存在下、ゾル−ゲル反応せしめ、得られた反応物をイミド化せしめてなる有機−無機ポリマーハイブリッドである請求項1〜請求項3の何れか1項に記載の気体分離膜。
R1 mM(OR2)n・・・式
R1 、R2 :炭化水素基
M:Si、Mg、Al、Zr又はTiの何れかの原子
m:0又は正の整数
n:正の整数
m+n:原子Mの原子価 - 前記ポリマーブレンドが直鎖ポリイミドを含むものである請求項1〜請求項5の何れか1項に記載の気体分離膜。
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