JPWO2011122560A1 - 複合半透膜 - Google Patents
複合半透膜 Download PDFInfo
- Publication number
- JPWO2011122560A1 JPWO2011122560A1 JP2011526730A JP2011526730A JPWO2011122560A1 JP WO2011122560 A1 JPWO2011122560 A1 JP WO2011122560A1 JP 2011526730 A JP2011526730 A JP 2011526730A JP 2011526730 A JP2011526730 A JP 2011526730A JP WO2011122560 A1 JPWO2011122560 A1 JP WO2011122560A1
- Authority
- JP
- Japan
- Prior art keywords
- semipermeable membrane
- composite semipermeable
- group
- membrane
- acid
- 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
- 239000012528 membrane Substances 0.000 title claims abstract description 117
- 239000002131 composite material Substances 0.000 title claims abstract description 66
- 238000000926 separation method Methods 0.000 claims abstract description 42
- 230000002378 acidificating effect Effects 0.000 claims abstract description 26
- 239000002346 layers by function Substances 0.000 claims abstract description 18
- 229920000642 polymer Polymers 0.000 claims abstract description 10
- 150000001875 compounds Chemical class 0.000 claims description 30
- 125000000524 functional group Chemical group 0.000 claims description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- ABLZXFCXXLZCGV-UHFFFAOYSA-N phosphonic acid group Chemical group P(O)(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 125000000542 sulfonic acid group Chemical group 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- 230000000379 polymerizing effect Effects 0.000 claims description 4
- 239000000178 monomer Substances 0.000 claims description 3
- 150000001450 anions Chemical class 0.000 claims description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 25
- 150000002500 ions Chemical class 0.000 abstract description 18
- 238000004519 manufacturing process Methods 0.000 abstract description 10
- 239000007859 condensation product Substances 0.000 abstract description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract description 2
- 239000000460 chlorine Substances 0.000 abstract description 2
- 229910052801 chlorine Inorganic materials 0.000 abstract description 2
- 238000010612 desalination reaction Methods 0.000 abstract description 2
- 239000003651 drinking water Substances 0.000 abstract description 2
- 235000020188 drinking water Nutrition 0.000 abstract description 2
- 230000007774 longterm Effects 0.000 abstract description 2
- RAXXELZNTBOGNW-UHFFFAOYSA-N 1H-imidazole Chemical group C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 abstract 1
- 239000013535 sea water Substances 0.000 abstract 1
- 239000011248 coating agent Substances 0.000 description 20
- 238000000576 coating method Methods 0.000 description 20
- 150000003839 salts Chemical class 0.000 description 20
- 239000007788 liquid Substances 0.000 description 19
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 18
- 239000010408 film Substances 0.000 description 15
- 238000000034 method Methods 0.000 description 14
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 11
- 230000000052 comparative effect Effects 0.000 description 10
- 238000006116 polymerization reaction Methods 0.000 description 10
- 239000010410 layer Substances 0.000 description 9
- 239000000463 material Substances 0.000 description 9
- 239000011148 porous material Substances 0.000 description 9
- 239000007864 aqueous solution Substances 0.000 description 8
- -1 acryloyloxy group Chemical group 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 239000012466 permeate Substances 0.000 description 5
- 229920002492 poly(sulfone) Polymers 0.000 description 5
- 239000003505 polymerization initiator Substances 0.000 description 5
- 239000010409 thin film Substances 0.000 description 5
- 238000006482 condensation reaction Methods 0.000 description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 4
- XFTALRAZSCGSKN-UHFFFAOYSA-M sodium;4-ethenylbenzenesulfonate Chemical compound [Na+].[O-]S(=O)(=O)C1=CC=C(C=C)C=C1 XFTALRAZSCGSKN-UHFFFAOYSA-M 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
- IRQWEODKXLDORP-UHFFFAOYSA-N 4-ethenylbenzoic acid Chemical compound OC(=O)C1=CC=C(C=C)C=C1 IRQWEODKXLDORP-UHFFFAOYSA-N 0.000 description 3
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000012965 benzophenone Substances 0.000 description 3
- 238000007664 blowing Methods 0.000 description 3
- 230000004907 flux Effects 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 238000001223 reverse osmosis Methods 0.000 description 3
- OTKCEEWUXHVZQI-UHFFFAOYSA-N 1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(=O)CC1=CC=CC=C1 OTKCEEWUXHVZQI-UHFFFAOYSA-N 0.000 description 2
- XMLYCEVDHLAQEL-UHFFFAOYSA-N 2-hydroxy-2-methyl-1-phenylpropan-1-one Chemical compound CC(C)(O)C(=O)C1=CC=CC=C1 XMLYCEVDHLAQEL-UHFFFAOYSA-N 0.000 description 2
- LWRBVKNFOYUCNP-UHFFFAOYSA-N 2-methyl-1-(4-methylsulfanylphenyl)-2-morpholin-4-ylpropan-1-one Chemical compound C1=CC(SC)=CC=C1C(=O)C(C)(C)N1CCOCC1 LWRBVKNFOYUCNP-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- MAGFQRLKWCCTQJ-UHFFFAOYSA-N 4-ethenylbenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=C(C=C)C=C1 MAGFQRLKWCCTQJ-UHFFFAOYSA-N 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 244000028419 Styrax benzoin Species 0.000 description 2
- 235000000126 Styrax benzoin Nutrition 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- 235000008411 Sumatra benzointree Nutrition 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 2
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 125000002843 carboxylic acid group Chemical group 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- 230000007547 defect Effects 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 235000019382 gum benzoic Nutrition 0.000 description 2
- 150000002430 hydrocarbons Chemical group 0.000 description 2
- 230000001678 irradiating effect Effects 0.000 description 2
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 2
- 239000004745 nonwoven fabric Substances 0.000 description 2
- 230000003204 osmotic effect Effects 0.000 description 2
- 238000012856 packing Methods 0.000 description 2
- 230000035515 penetration Effects 0.000 description 2
- 230000035699 permeability Effects 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229920002647 polyamide Polymers 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 229920006267 polyester film Polymers 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- IREVRWRNACELSM-UHFFFAOYSA-J ruthenium(4+);tetrachloride Chemical compound Cl[Ru](Cl)(Cl)Cl IREVRWRNACELSM-UHFFFAOYSA-J 0.000 description 2
- ZTWTYVWXUKTLCP-UHFFFAOYSA-N vinylphosphonic acid Chemical compound OP(O)(=O)C=C ZTWTYVWXUKTLCP-UHFFFAOYSA-N 0.000 description 2
- NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical compound OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 description 2
- ZZCNGCMJBJERQI-UHFFFAOYSA-N (1-prop-2-enoylpiperidin-4-yl) dihydrogen phosphate Chemical compound OP(O)(=O)OC1CCN(C(=O)C=C)CC1 ZZCNGCMJBJERQI-UHFFFAOYSA-N 0.000 description 1
- HJIAMFHSAAEUKR-UHFFFAOYSA-N (2-hydroxyphenyl)-phenylmethanone Chemical compound OC1=CC=CC=C1C(=O)C1=CC=CC=C1 HJIAMFHSAAEUKR-UHFFFAOYSA-N 0.000 description 1
- IJAOUFAMBRPHSJ-UHFFFAOYSA-N (4-ethenylphenyl)methylphosphonic acid Chemical compound OP(O)(=O)CC1=CC=C(C=C)C=C1 IJAOUFAMBRPHSJ-UHFFFAOYSA-N 0.000 description 1
- CJBYXOUKKQTXPF-UHFFFAOYSA-N (4-ethenylphenyl)phosphonic acid Chemical compound OP(O)(=O)C1=CC=C(C=C)C=C1 CJBYXOUKKQTXPF-UHFFFAOYSA-N 0.000 description 1
- MSAHTMIQULFMRG-UHFFFAOYSA-N 1,2-diphenyl-2-propan-2-yloxyethanone Chemical compound C=1C=CC=CC=1C(OC(C)C)C(=O)C1=CC=CC=C1 MSAHTMIQULFMRG-UHFFFAOYSA-N 0.000 description 1
- DKEGCUDAFWNSSO-UHFFFAOYSA-N 1,8-dibromooctane Chemical compound BrCCCCCCCCBr DKEGCUDAFWNSSO-UHFFFAOYSA-N 0.000 description 1
- MLKIVXXYTZKNMI-UHFFFAOYSA-N 1-(4-dodecylphenyl)-2-hydroxy-2-methylpropan-1-one Chemical compound CCCCCCCCCCCCC1=CC=C(C(=O)C(C)(C)O)C=C1 MLKIVXXYTZKNMI-UHFFFAOYSA-N 0.000 description 1
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 1
- YENKRZXDJWBUIY-UHFFFAOYSA-N 1-phosphonooxypropan-2-yl 2-methylprop-2-enoate Chemical compound OP(=O)(O)OCC(C)OC(=O)C(C)=C YENKRZXDJWBUIY-UHFFFAOYSA-N 0.000 description 1
- CFKBCVIYTWDYRP-UHFFFAOYSA-N 10-phosphonooxydecyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCCCCCCCCOP(O)(O)=O CFKBCVIYTWDYRP-UHFFFAOYSA-N 0.000 description 1
- PIZHFBODNLEQBL-UHFFFAOYSA-N 2,2-diethoxy-1-phenylethanone Chemical compound CCOC(OCC)C(=O)C1=CC=CC=C1 PIZHFBODNLEQBL-UHFFFAOYSA-N 0.000 description 1
- KWVGIHKZDCUPEU-UHFFFAOYSA-N 2,2-dimethoxy-2-phenylacetophenone Chemical compound C=1C=CC=CC=1C(OC)(OC)C(=O)C1=CC=CC=C1 KWVGIHKZDCUPEU-UHFFFAOYSA-N 0.000 description 1
- UHWLJHBFRWUMNP-UHFFFAOYSA-N 2-(2-methylprop-2-enoylamino)ethylphosphonic acid Chemical compound CC(=C)C(=O)NCCP(O)(O)=O UHWLJHBFRWUMNP-UHFFFAOYSA-N 0.000 description 1
- OKKJMXCNNZVCPO-UHFFFAOYSA-N 2-(2-methylprop-2-enoyloxy)ethylphosphonic acid Chemical compound CC(=C)C(=O)OCCP(O)(O)=O OKKJMXCNNZVCPO-UHFFFAOYSA-N 0.000 description 1
- XXEYEDZRUQKMLI-UHFFFAOYSA-N 2-(2-phosphonoethoxymethyl)prop-2-enoic acid Chemical compound OC(=O)C(=C)COCCP(O)(O)=O XXEYEDZRUQKMLI-UHFFFAOYSA-N 0.000 description 1
- IEQWWMKDFZUMMU-UHFFFAOYSA-N 2-(2-prop-2-enoyloxyethyl)butanedioic acid Chemical compound OC(=O)CC(C(O)=O)CCOC(=O)C=C IEQWWMKDFZUMMU-UHFFFAOYSA-N 0.000 description 1
- PUBNJSZGANKUGX-UHFFFAOYSA-N 2-(dimethylamino)-2-[(4-methylphenyl)methyl]-1-(4-morpholin-4-ylphenyl)butan-1-one Chemical compound C=1C=C(N2CCOCC2)C=CC=1C(=O)C(CC)(N(C)C)CC1=CC=C(C)C=C1 PUBNJSZGANKUGX-UHFFFAOYSA-N 0.000 description 1
- AAMTXHVZOHPPQR-UHFFFAOYSA-N 2-(hydroxymethyl)prop-2-enoic acid Chemical compound OCC(=C)C(O)=O AAMTXHVZOHPPQR-UHFFFAOYSA-N 0.000 description 1
- GPLACOONWGSIIP-UHFFFAOYSA-N 2-(n-[2-hydroxy-3-(2-methylprop-2-enoyloxy)propyl]anilino)acetic acid Chemical compound CC(=C)C(=O)OCC(O)CN(CC(O)=O)C1=CC=CC=C1 GPLACOONWGSIIP-UHFFFAOYSA-N 0.000 description 1
- GJKGAPPUXSSCFI-UHFFFAOYSA-N 2-Hydroxy-4'-(2-hydroxyethoxy)-2-methylpropiophenone Chemical compound CC(C)(O)C(=O)C1=CC=C(OCCO)C=C1 GJKGAPPUXSSCFI-UHFFFAOYSA-N 0.000 description 1
- AZCYBBHXCQYWTO-UHFFFAOYSA-N 2-[(2-chloro-6-fluorophenyl)methoxy]benzaldehyde Chemical compound FC1=CC=CC(Cl)=C1COC1=CC=CC=C1C=O AZCYBBHXCQYWTO-UHFFFAOYSA-N 0.000 description 1
- JDKSTARXLKKYPS-UHFFFAOYSA-N 2-[10-(2-methylprop-2-enoyloxy)decyl]propanedioic acid Chemical compound CC(=C)C(=O)OCCCCCCCCCCC(C(O)=O)C(O)=O JDKSTARXLKKYPS-UHFFFAOYSA-N 0.000 description 1
- LBNDGEZENJUBCO-UHFFFAOYSA-N 2-[2-(2-methylprop-2-enoyloxy)ethyl]butanedioic acid Chemical compound CC(=C)C(=O)OCCC(C(O)=O)CC(O)=O LBNDGEZENJUBCO-UHFFFAOYSA-N 0.000 description 1
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 1
- FGTYTUFKXYPTML-UHFFFAOYSA-N 2-benzoylbenzoic acid Chemical compound OC(=O)C1=CC=CC=C1C(=O)C1=CC=CC=C1 FGTYTUFKXYPTML-UHFFFAOYSA-N 0.000 description 1
- ZCDADJXRUCOCJE-UHFFFAOYSA-N 2-chlorothioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(Cl)=CC=C3SC2=C1 ZCDADJXRUCOCJE-UHFFFAOYSA-N 0.000 description 1
- VMSBGXAJJLPWKV-UHFFFAOYSA-N 2-ethenylbenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1C=C VMSBGXAJJLPWKV-UHFFFAOYSA-N 0.000 description 1
- XUDBVJCTLZTSDC-UHFFFAOYSA-N 2-ethenylbenzoic acid Chemical compound OC(=O)C1=CC=CC=C1C=C XUDBVJCTLZTSDC-UHFFFAOYSA-N 0.000 description 1
- KMNCBSZOIQAUFX-UHFFFAOYSA-N 2-ethoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OCC)C(=O)C1=CC=CC=C1 KMNCBSZOIQAUFX-UHFFFAOYSA-N 0.000 description 1
- FJXHGUOSFCDKJT-UHFFFAOYSA-N 2-ethyl-4-methoxypentanoic acid Chemical compound C(C)C(C(=O)O)CC(C)OC FJXHGUOSFCDKJT-UHFFFAOYSA-N 0.000 description 1
- PCKZAVNWRLEHIP-UHFFFAOYSA-N 2-hydroxy-1-[4-[[4-(2-hydroxy-2-methylpropanoyl)phenyl]methyl]phenyl]-2-methylpropan-1-one Chemical compound C1=CC(C(=O)C(C)(O)C)=CC=C1CC1=CC=C(C(=O)C(C)(C)O)C=C1 PCKZAVNWRLEHIP-UHFFFAOYSA-N 0.000 description 1
- BQZJOQXSCSZQPS-UHFFFAOYSA-N 2-methoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OC)C(=O)C1=CC=CC=C1 BQZJOQXSCSZQPS-UHFFFAOYSA-N 0.000 description 1
- MCIIDRLDHRQKPH-UHFFFAOYSA-N 2-methyl-3-phenylpropanoic acid Chemical compound OC(=O)C(C)CC1=CC=CC=C1 MCIIDRLDHRQKPH-UHFFFAOYSA-N 0.000 description 1
- MYISVPVWAQRUTL-UHFFFAOYSA-N 2-methylthioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(C)=CC=C3SC2=C1 MYISVPVWAQRUTL-UHFFFAOYSA-N 0.000 description 1
- MWDGNKGKLOBESZ-UHFFFAOYSA-N 2-oxooctanal Chemical compound CCCCCCC(=O)C=O MWDGNKGKLOBESZ-UHFFFAOYSA-N 0.000 description 1
- SEILKFZTLVMHRR-UHFFFAOYSA-N 2-phosphonooxyethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOP(O)(O)=O SEILKFZTLVMHRR-UHFFFAOYSA-N 0.000 description 1
- XDXCRCUBZYXJFW-UHFFFAOYSA-M 3-(3-ethenylimidazol-1-ium-1-yl)propyl-trimethoxysilane;chloride Chemical group [Cl-].CO[Si](OC)(OC)CCC[N+]=1C=CN(C=C)C=1 XDXCRCUBZYXJFW-UHFFFAOYSA-M 0.000 description 1
- RUEMJMLXCZVLPB-UHFFFAOYSA-M 3-[3-[(4-ethenylphenyl)methyl]imidazol-3-ium-1-yl]propyl-trimethoxysilane;chloride Chemical group [Cl-].CO[Si](OC)(OC)CCCN1C=C[N+](CC=2C=CC(C=C)=CC=2)=C1 RUEMJMLXCZVLPB-UHFFFAOYSA-M 0.000 description 1
- OXYZDRAJMHGSMW-UHFFFAOYSA-N 3-chloropropyl(trimethoxy)silane Chemical group CO[Si](OC)(OC)CCCCl OXYZDRAJMHGSMW-UHFFFAOYSA-N 0.000 description 1
- ATBDZSAENDYQDW-UHFFFAOYSA-N 3-ethenylbenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC(C=C)=C1 ATBDZSAENDYQDW-UHFFFAOYSA-N 0.000 description 1
- VWXZFDWVWMQRQR-UHFFFAOYSA-N 3-ethenylbenzoic acid Chemical compound OC(=O)C1=CC=CC(C=C)=C1 VWXZFDWVWMQRQR-UHFFFAOYSA-N 0.000 description 1
- MKTOIPPVFPJEQO-UHFFFAOYSA-N 4-(3-carboxypropanoylperoxy)-4-oxobutanoic acid Chemical compound OC(=O)CCC(=O)OOC(=O)CCC(O)=O MKTOIPPVFPJEQO-UHFFFAOYSA-N 0.000 description 1
- OXEZLYIDQPBCBB-UHFFFAOYSA-N 4-(3-piperidin-4-ylpropyl)piperidine Chemical compound C1CNCCC1CCCC1CCNCC1 OXEZLYIDQPBCBB-UHFFFAOYSA-N 0.000 description 1
- LUOHHCFFFGGPPJ-UHFFFAOYSA-M 5-[3-(3-trimethoxysilylpropyl)imidazol-3-ium-1-yl]pent-1-en-3-one;chloride Chemical group [Cl-].CO[Si](OC)(OC)CCC[N+]=1C=CN(CCC(=O)C=C)C=1 LUOHHCFFFGGPPJ-UHFFFAOYSA-M 0.000 description 1
- PIEJYLBGEXCEPO-UHFFFAOYSA-N 7-cyanooctanoic acid Chemical compound N#CC(C)CCCCCC(O)=O PIEJYLBGEXCEPO-UHFFFAOYSA-N 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical group NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- AGQZVSNXFMEEPJ-UHFFFAOYSA-N C1(=CC=CC=C1)C(=O)C1(C(C(CCC1)(C(C)(C)O)C1=CC=C(C=C1)OCCO)=O)O Chemical compound C1(=CC=CC=C1)C(=O)C1(C(C(CCC1)(C(C)(C)O)C1=CC=C(C=C1)OCCO)=O)O AGQZVSNXFMEEPJ-UHFFFAOYSA-N 0.000 description 1
- ZGFPUTOTEJOSAY-UHFFFAOYSA-N FC1=C([Ti])C(F)=CC=C1N1C=CC=C1 Chemical compound FC1=C([Ti])C(F)=CC=C1N1C=CC=C1 ZGFPUTOTEJOSAY-UHFFFAOYSA-N 0.000 description 1
- BQMUDSHSOGAUBC-UHFFFAOYSA-N P(=O)(OCCOC(C(=C)C)=O)(O)O.P(=O)(OCC(C)OC(C(=C)C)=O)(O)O Chemical compound P(=O)(OCCOC(C(=C)C)=O)(O)O.P(=O)(OCC(C)OC(C(=C)C)=O)(O)O BQMUDSHSOGAUBC-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- GULGRQIYDXNGCN-UHFFFAOYSA-N [4-methyl-4-(2-methylprop-2-enoylamino)cyclohexa-1,5-dien-1-yl]phosphonic acid Chemical compound CC(=C)C(=O)NC1(C)CC=C(P(O)(O)=O)C=C1 GULGRQIYDXNGCN-UHFFFAOYSA-N 0.000 description 1
- GUCYFKSBFREPBC-UHFFFAOYSA-N [phenyl-(2,4,6-trimethylbenzoyl)phosphoryl]-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C(=O)C1=C(C)C=C(C)C=C1C GUCYFKSBFREPBC-UHFFFAOYSA-N 0.000 description 1
- 230000001133 acceleration Effects 0.000 description 1
- 150000008062 acetophenones Chemical class 0.000 description 1
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- ARCGXLSVLAOJQL-UHFFFAOYSA-N anhydrous trimellitic acid Natural products OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 1
- 239000004760 aramid Substances 0.000 description 1
- 229920003235 aromatic polyamide Polymers 0.000 description 1
- UWCPYKQBIPYOLX-UHFFFAOYSA-N benzene-1,3,5-tricarbonyl chloride Chemical compound ClC(=O)C1=CC(C(Cl)=O)=CC(C(Cl)=O)=C1 UWCPYKQBIPYOLX-UHFFFAOYSA-N 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
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- 230000015572 biosynthetic process Effects 0.000 description 1
- MQDJYUACMFCOFT-UHFFFAOYSA-N bis[2-(1-hydroxycyclohexyl)phenyl]methanone Chemical compound C=1C=CC=C(C(=O)C=2C(=CC=CC=2)C2(O)CCCCC2)C=1C1(O)CCCCC1 MQDJYUACMFCOFT-UHFFFAOYSA-N 0.000 description 1
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- 238000003618 dip coating Methods 0.000 description 1
- 238000010494 dissociation reaction Methods 0.000 description 1
- 230000005593 dissociations Effects 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000010894 electron beam technology Methods 0.000 description 1
- 238000000635 electron micrograph Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000012527 feed solution Substances 0.000 description 1
- 238000000445 field-emission scanning electron microscopy Methods 0.000 description 1
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- 150000004820 halides Chemical class 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 150000004693 imidazolium salts Chemical group 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 230000009878 intermolecular interaction Effects 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 1
- 238000001471 micro-filtration Methods 0.000 description 1
- 238000001728 nano-filtration Methods 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 229920000620 organic polymer Polymers 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
- LYXOWKPVTCPORE-UHFFFAOYSA-N phenyl-(4-phenylphenyl)methanone Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1C(=O)C1=CC=CC=C1 LYXOWKPVTCPORE-UHFFFAOYSA-N 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical group O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229920006149 polyester-amide block copolymer Polymers 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- UIIIBRHUICCMAI-UHFFFAOYSA-N prop-2-ene-1-sulfonic acid Chemical compound OS(=O)(=O)CC=C UIIIBRHUICCMAI-UHFFFAOYSA-N 0.000 description 1
- RZKYDQNMAUSEDZ-UHFFFAOYSA-N prop-2-enylphosphonic acid Chemical compound OP(O)(=O)CC=C RZKYDQNMAUSEDZ-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 150000003377 silicon compounds Chemical class 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 125000000626 sulfinic acid group Chemical group 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- VBCHPEHFLCAQHA-UHFFFAOYSA-M trimethoxy-[3-(3-methylimidazol-3-ium-1-yl)propyl]silane;chloride Chemical group [Cl-].CO[Si](OC)(OC)CCCN1C=C[N+](C)=C1 VBCHPEHFLCAQHA-UHFFFAOYSA-M 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 229910000406 trisodium phosphate Inorganic materials 0.000 description 1
- 235000019801 trisodium phosphate Nutrition 0.000 description 1
- 238000000108 ultra-filtration Methods 0.000 description 1
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
Classifications
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- 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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- B01D65/022—Membrane sterilisation
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- B01D69/10—Supported membranes; Membrane supports
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- B01D71/76—Macromolecular material not specifically provided for in a single one of groups B01D71/08 - B01D71/74
- B01D71/78—Graft polymers
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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
- C08G77/04—Polysiloxanes
- C08G77/22—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
- C08G77/26—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen nitrogen-containing groups
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- C—CHEMISTRY; METALLURGY
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- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
- C08L83/04—Polysiloxanes
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- B01D2321/34—Details relating to membrane cleaning, regeneration, sterilization or to the prevention of fouling by radiation
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Abstract
Description
(II)酸性基がカルボキシル基、スルホン酸基、およびホスホン酸基のうちから選ばれる、少なくとも1種であることを特徴とする、(I)に記載の複合半透膜。
Flux(m/d)=(一日の透過液量)/(膜面積) ・・・式(4)
実施例1
21cm×15cmのポリエステル不織布(通気度0.5〜1cc/cm2/sec)上にポリスルホンの15.3重量%ジメチルホルムアミド(DMF)溶液を200μmの厚みで室温(25℃)でキャストし、ただちに純水中に浸漬して5分間放置することによって微多孔性支持膜を作製した。
塗液Aをp−スチレンスルホン酸ナトリウム1.5重量部、1−アリル−3−(3−トリメトキシシリルプロピル)イミダゾリウムクロリド3.5重量部、2,2−ジメトキシ−1,2−ジフェニルエタン−1−オン0.15重量部、65%イソプロピルアルコール水溶液94.76重量部からなる塗液Bに代え、172nmの紫外線が照射できるウシオ電機社製エキシマランプUER20−172を用い、照射窓と微多孔性支持膜の距離を1cmに設定し紫外線を10分間照射する工程を365nmの紫外線が照射できるハリソン東芝ライティング社製UV照射装置TOSCURE752を用い、照射強度を20mW/cm2に設定し、紫外線を30分間照射する工程に代える以外は実施例1と同様にして複合半透膜を作製した。また、このようにして得られた複合半透膜を実施例1と同様にして評価を行い、表1に示す性能が得られた。
実施例1で使用した1−アリル−3−(3−トリメトキシシリルプロピル)イミダゾリウムクロリドを1−(2−アクリロイルエチル)−3−(3−トリメトキシシリルプロピル)イミダゾリウムクロリドに代える以外は実施例1と同様にして複合半透膜を作製した。また、このようにして得られた複合半透膜を実施例1と同様にして評価を行い、表1に示す性能が得られた。
実施例1で使用した1−アリル−3−(3−トリメトキシシリルプロピル)イミダゾリウムクロリドを1−(4−ビニルベンジル)−3−(3−トリメトキシシリルプロピル)イミダゾリウムクロリドに代える以外は実施例1と同様にして複合半透膜を作製した。また、このようにして得られた複合半透膜を実施例1と同様にして評価を行い、表1に示す性能が得られた。
実施例1で使用した1−アリル−3−(3−トリメトキシシリルプロピル)イミダゾリウムクロリドを1−ビニル−3−(3−トリメトキシシリルプロピル)イミダゾリウムクロリドに代える以外は実施例1と同様にして複合半透膜を作製した。また、このようにして得られた複合半透膜を実施例1と同様にして評価を行い、表1に示す性能が得られた。
実施例1で使用した塗液Aをアクリル酸0.8重量部、1−アリル−3−(3−トリメトキシシリルプロピル)イミダゾリウムクロリド3.0重量部、2,2−ジメトキシ−1,2−ジフェニルエタン−1−オン0.14重量部、65%イソプロピルアルコール水溶液96.06重量部からなる塗液Cに代える以外は実施例1と同様にして複合半透膜を作製した。また、このようにして得られた複合半透膜を実施例1と同様にして評価を行い、表1に示す性能が得られた。
実施例1で使用した塗液Aをp-ビニル安息香酸1.0重量部、1−アリル−3−(3−トリメトキシシリルプロピル)イミダゾリウムクロリド3.0重量部、2,2−ジメトキシ−1,2−ジフェニルエタン−1−オン0.14重量部、65%イソプロピルアルコール水溶液95.86重量部からなる塗液Cに代える以外は実施例1と同様にして複合半透膜を作製した。また、このようにして得られた複合半透膜を実施例1と同様にして評価を行い、表1に示す性能が得られた。
実施例1と同様の方法にて作製した微多孔性支持膜上に、ピペラジン0.8重量%、1,3−ビス(4−ピペリジル)プロパン0.2重量%、界面活性剤(日本乳化剤(株)製、ニューコール271A)0.5重量%、リン酸三ナトリウム1.0重量%を含有した水溶液を塗布し、エアーナイフで液切りした後、120℃の温風で40秒間風乾した。その後、トリメシン酸クロライドの0.3重量%デカン溶液を塗布し、その後、100℃の熱風で5分間熱処理し、反応を進行させてから、炭酸ナトリウム5.0重量%とドデシル硫酸ナトリウム0.1重量%からなるアルカリ水溶液を塗布して反応を停止させ、複合半透膜を得た。また、このようにして得られた複合半透膜を実施例1と同様にして評価を行い、表1に示す性能が得られた。
1−アリル−3−(3−トリメトキシシリルプロピル)イミダゾリウムクロリドを3−メチル−1−(3−トリメトキシシリルプロピル)イミダゾリウムクロリドに代える以外は実施例1と同様にして複合半透膜を作製した。また、このようにして得られた複合半透膜を実施例1と同様にして評価を行い、表1に示す性能が得られた。
1−アリル−3−(3−トリメトキシシリルプロピル)イミダゾリウムクロリドを3−クロロプロピルトリメトキシシランに代える以外は実施例1と同様にして複合半透膜を作製した。また、このようにして得られた複合半透膜を実施例1と同様にして評価を行い、表1に示す性能が得られた。
実施例1における反応液中に、1−アリル−3−(3−トリメトキシシリルプロピル)イミダゾリウムクロリドを含まず、p−スチレンスルホン酸ナトリウムを5重量%とする以外は実施例1と同様にして複合半透膜を作製した。得られた複合半透膜を実施例1と同様にして評価を行い、表1に示す結果が得られた。
実施例1における反応液中に、p−スチレンスルホン酸ナトリウムを含まず、1−アリル−3−(3−トリメトキシシリルプロピル)イミダゾリウムクロリドを5重量%とする以外は実施例1と同様にして複合半透膜を作製した。得られた複合半透膜を実施例1と同様にして評価を行い、表1に示す結果が得られた。
Claims (3)
- 酸性基がカルボキシル基、スルホン酸基、およびホスホン酸基のうちから選ばれる、少なくとも1種であることを特徴とする、請求項1に記載の複合半透膜。
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EP (1) | EP2554249B1 (ja) |
JP (1) | JP5776550B2 (ja) |
KR (1) | KR101744207B1 (ja) |
CN (1) | CN102834167B (ja) |
AU (1) | AU2011235748A1 (ja) |
SG (1) | SG183809A1 (ja) |
WO (1) | WO2011122560A1 (ja) |
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KR101746868B1 (ko) * | 2009-03-31 | 2017-06-14 | 도레이 카부시키가이샤 | 복합 반투막 및 그의 제조 방법 |
US8757396B2 (en) * | 2010-05-24 | 2014-06-24 | Dow Global Technologies Llc | Composite membrane with coating comprising polyalkylene oxide and oxy-substituted phenyl compounds |
WO2013066941A1 (en) * | 2011-10-31 | 2013-05-10 | The Board Of Trustees Of The University Of Arkansas | Catalytic membranes and applications thereof |
JP6206043B2 (ja) * | 2013-09-30 | 2017-10-04 | 東レ株式会社 | 複合半透膜およびその製造方法 |
CN104927079B (zh) * | 2015-07-10 | 2018-03-02 | 常州大学 | 一种碱性阴离子交换膜的制备方法 |
Family Cites Families (19)
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JPS6064601A (ja) * | 1983-09-17 | 1985-04-13 | Agency Of Ind Science & Technol | 気体選択透過膜 |
JPH01180208A (ja) | 1988-01-11 | 1989-07-18 | Toray Ind Inc | 複合半透膜の製造方法およびその膜 |
JPH0664601A (ja) | 1992-11-14 | 1994-03-08 | Tokyo Shokai:Kk | 錠剤分包機の錠剤供給装置 |
JP4022639B2 (ja) * | 1998-04-28 | 2007-12-19 | 東ソー株式会社 | 有機・無機ハイブリッド材料及びその製造方法 |
DE10021104A1 (de) * | 2000-05-02 | 2001-11-08 | Univ Stuttgart | Organisch-anorganische Membranen |
JP3513097B2 (ja) | 2000-09-29 | 2004-03-31 | 株式会社東芝 | プロトン伝導性膜およびそれを用いた燃料電池 |
DE10061959A1 (de) | 2000-12-13 | 2002-06-20 | Creavis Tech & Innovation Gmbh | Kationen-/protonenleitende, mit einer ionischen Flüssigkeit infiltrierte keramische Membran, Verfahren zu deren Herstellung und die Verwendung der Membran |
DE10163518A1 (de) * | 2001-12-21 | 2003-07-10 | Fraunhofer Ges Forschung | Protonenleitfähige Membranen/Schichten und Verfahren zu deren Herstellung |
CA2477863A1 (en) * | 2002-03-06 | 2003-09-12 | Pemeas Gmbh | Mixtures comprising vinyl-containing sulphonic acid, polymer electrolyte membranes comprising polyvinylsulphonic acid and their use in fuel cells |
JP2004025610A (ja) * | 2002-06-25 | 2004-01-29 | Toray Ind Inc | 積層フィルムおよびその製造方法 |
FR2850301B1 (fr) | 2003-01-23 | 2007-10-19 | Commissariat Energie Atomique | Materiau hybride organique-inorganique comprenant une phase minerale mesoporeuse et une phase organique, membrane et pile a combustible |
JP4175174B2 (ja) * | 2003-05-15 | 2008-11-05 | 東レ株式会社 | コンポジット材料及びその製造方法 |
JP2005144211A (ja) | 2003-11-11 | 2005-06-09 | Toray Ind Inc | 複合半透膜及びその製造方法ならびに流体分離素子の処理方法 |
JP2006244920A (ja) * | 2005-03-04 | 2006-09-14 | Fujitsu Ltd | 固体電解質組成物および高分子型燃料電池 |
CA2693896C (en) * | 2007-07-19 | 2016-02-09 | Shell Internationale Research Maatschappij B.V. | Water processing systems and methods |
EP2327469A4 (en) | 2008-09-12 | 2015-09-16 | Toray Industries | Semi-transparent composite film and method for its production |
KR101746868B1 (ko) * | 2009-03-31 | 2017-06-14 | 도레이 카부시키가이샤 | 복합 반투막 및 그의 제조 방법 |
KR101923014B1 (ko) * | 2010-12-07 | 2018-11-28 | 도레이 카부시키가이샤 | 복합 반투막 및 그 제조 방법 |
WO2012075574A1 (en) * | 2010-12-09 | 2012-06-14 | Queen's University At Kingston | Azolium ionomer derivatives of halogenated polymers |
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US8672143B2 (en) | 2014-03-18 |
SG183809A1 (en) | 2012-10-30 |
JP5776550B2 (ja) | 2015-09-09 |
US20130032530A1 (en) | 2013-02-07 |
KR101744207B1 (ko) | 2017-06-07 |
WO2011122560A1 (ja) | 2011-10-06 |
CN102834167B (zh) | 2014-11-05 |
KR20130038195A (ko) | 2013-04-17 |
EP2554249B1 (en) | 2016-02-10 |
EP2554249A4 (en) | 2013-12-04 |
CN102834167A (zh) | 2012-12-19 |
AU2011235748A1 (en) | 2012-09-27 |
EP2554249A1 (en) | 2013-02-06 |
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