JP5964292B2 - 薄膜複合材 - Google Patents
薄膜複合材 Download PDFInfo
- Publication number
- JP5964292B2 JP5964292B2 JP2013513129A JP2013513129A JP5964292B2 JP 5964292 B2 JP5964292 B2 JP 5964292B2 JP 2013513129 A JP2013513129 A JP 2013513129A JP 2013513129 A JP2013513129 A JP 2013513129A JP 5964292 B2 JP5964292 B2 JP 5964292B2
- Authority
- JP
- Japan
- Prior art keywords
- liquid phase
- thin film
- film composite
- manufacturing
- production method
- 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
- 239000010409 thin film Substances 0.000 title claims description 45
- 239000002131 composite material Substances 0.000 title claims description 41
- 150000001266 acyl halides Chemical class 0.000 claims description 48
- 150000001412 amines Chemical class 0.000 claims description 42
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 41
- 238000000034 method Methods 0.000 claims description 38
- 239000007791 liquid phase Substances 0.000 claims description 32
- 238000004519 manufacturing process Methods 0.000 claims description 30
- 239000002904 solvent Substances 0.000 claims description 30
- 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 claims description 18
- 239000002253 acid Substances 0.000 claims description 16
- 150000004820 halides Chemical group 0.000 claims description 14
- 125000003277 amino group Chemical group 0.000 claims description 13
- 238000000926 separation method Methods 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 11
- LZDKZFUFMNSQCJ-UHFFFAOYSA-N 1,2-diethoxyethane Chemical compound CCOCCOCC LZDKZFUFMNSQCJ-UHFFFAOYSA-N 0.000 claims description 7
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 claims description 7
- 238000010612 desalination reaction Methods 0.000 claims description 7
- 229940018564 m-phenylenediamine Drugs 0.000 claims description 6
- 229920002678 cellulose Polymers 0.000 claims description 5
- 239000001913 cellulose Substances 0.000 claims description 5
- 229920002301 cellulose acetate Polymers 0.000 claims description 5
- 125000000524 functional group Chemical group 0.000 claims description 5
- 239000012442 inert solvent Substances 0.000 claims description 5
- 125000003010 ionic group Chemical group 0.000 claims description 5
- JSYBAZQQYCNZJE-UHFFFAOYSA-N benzene-1,2,4-triamine Chemical compound NC1=CC=C(N)C(N)=C1 JSYBAZQQYCNZJE-UHFFFAOYSA-N 0.000 claims description 4
- 238000001728 nano-filtration Methods 0.000 claims description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 3
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 claims description 3
- 230000002209 hydrophobic effect Effects 0.000 claims description 3
- 239000004627 regenerated cellulose Substances 0.000 claims description 3
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 claims description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 claims 2
- 239000003350 kerosene Substances 0.000 claims 2
- RUOKPLVTMFHRJE-UHFFFAOYSA-N benzene-1,2,3-triamine Chemical compound NC1=CC=CC(N)=C1N RUOKPLVTMFHRJE-UHFFFAOYSA-N 0.000 claims 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims 1
- 238000000909 electrodialysis Methods 0.000 claims 1
- 239000000446 fuel Substances 0.000 claims 1
- 239000012528 membrane Substances 0.000 description 90
- 239000000243 solution Substances 0.000 description 26
- 238000001223 reverse osmosis Methods 0.000 description 19
- 238000012695 Interfacial polymerization Methods 0.000 description 17
- 150000003839 salts Chemical class 0.000 description 17
- 230000008569 process Effects 0.000 description 15
- 239000011148 porous material Substances 0.000 description 13
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 239000010408 film Substances 0.000 description 12
- 125000003118 aryl group Chemical group 0.000 description 11
- 238000006116 polymerization reaction Methods 0.000 description 10
- 230000003111 delayed effect Effects 0.000 description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- 239000012071 phase Substances 0.000 description 8
- 238000009792 diffusion process Methods 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 6
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- 239000004952 Polyamide Substances 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 239000000178 monomer Substances 0.000 description 6
- 229920002647 polyamide Polymers 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 6
- 239000000376 reactant Substances 0.000 description 6
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 5
- 125000001931 aliphatic group Chemical group 0.000 description 5
- 238000007598 dipping method Methods 0.000 description 5
- 239000007789 gas Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 229920006254 polymer film Polymers 0.000 description 5
- 230000002787 reinforcement Effects 0.000 description 5
- MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical compound C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-N 0.000 description 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- -1 aromatic acyl halides Chemical class 0.000 description 4
- 230000004888 barrier function Effects 0.000 description 4
- 239000012530 fluid Substances 0.000 description 4
- 230000004907 flux Effects 0.000 description 4
- 238000001764 infiltration Methods 0.000 description 4
- 230000008595 infiltration Effects 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 4
- 241000894007 species Species 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- 125000000777 acyl halide group Chemical group 0.000 description 3
- 239000000010 aprotic solvent Substances 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- FDQSRULYDNDXQB-UHFFFAOYSA-N benzene-1,3-dicarbonyl chloride Chemical compound ClC(=O)C1=CC=CC(C(Cl)=O)=C1 FDQSRULYDNDXQB-UHFFFAOYSA-N 0.000 description 3
- 238000007385 chemical modification Methods 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 230000032798 delamination Effects 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 230000018109 developmental process Effects 0.000 description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 230000003204 osmotic effect Effects 0.000 description 3
- 230000035699 permeability Effects 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- LXEJRKJRKIFVNY-UHFFFAOYSA-N terephthaloyl chloride Chemical compound ClC(=O)C1=CC=C(C(Cl)=O)C=C1 LXEJRKJRKIFVNY-UHFFFAOYSA-N 0.000 description 3
- 150000003512 tertiary amines Chemical class 0.000 description 3
- 238000009736 wetting Methods 0.000 description 3
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 2
- UTMWFJSRHLYRPY-UHFFFAOYSA-N 3,3',5,5'-tetrachlorobiphenyl Chemical group ClC1=CC(Cl)=CC(C=2C=C(Cl)C=C(Cl)C=2)=C1 UTMWFJSRHLYRPY-UHFFFAOYSA-N 0.000 description 2
- QYAMZFPPWQRILI-UHFFFAOYSA-N 5-isocyanatobenzene-1,3-dicarbonyl chloride Chemical compound ClC(=O)C1=CC(N=C=O)=CC(C(Cl)=O)=C1 QYAMZFPPWQRILI-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- 208000029422 Hypernatremia Diseases 0.000 description 2
- 239000004697 Polyetherimide Substances 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 230000003487 anti-permeability effect Effects 0.000 description 2
- 239000004760 aramid Substances 0.000 description 2
- 229920003235 aromatic polyamide Polymers 0.000 description 2
- 239000000872 buffer Substances 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 238000005266 casting Methods 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 238000011033 desalting Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- 150000007524 organic acids Chemical group 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000012466 permeate Substances 0.000 description 2
- 229920002492 poly(sulfone) Polymers 0.000 description 2
- 229920001601 polyetherimide Polymers 0.000 description 2
- 229920005597 polymer membrane Polymers 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 125000001174 sulfone group Chemical group 0.000 description 2
- 229940086542 triethylamine Drugs 0.000 description 2
- ZLYYJUJDFKGVKB-OWOJBTEDSA-N (e)-but-2-enedioyl dichloride Chemical compound ClC(=O)\C=C\C(Cl)=O ZLYYJUJDFKGVKB-OWOJBTEDSA-N 0.000 description 1
- BOSAWIQFTJIYIS-UHFFFAOYSA-N 1,1,1-trichloro-2,2,2-trifluoroethane Chemical compound FC(F)(F)C(Cl)(Cl)Cl BOSAWIQFTJIYIS-UHFFFAOYSA-N 0.000 description 1
- BAHPQISAXRFLCL-UHFFFAOYSA-N 2,4-Diaminoanisole Chemical compound COC1=CC=C(N)C=C1N BAHPQISAXRFLCL-UHFFFAOYSA-N 0.000 description 1
- VOZKAJLKRJDJLL-UHFFFAOYSA-N 2,4-diaminotoluene Chemical compound CC1=CC=C(N)C=C1N VOZKAJLKRJDJLL-UHFFFAOYSA-N 0.000 description 1
- NSMWYRLQHIXVAP-UHFFFAOYSA-N 2,5-dimethylpiperazine Chemical compound CC1CNC(C)CN1 NSMWYRLQHIXVAP-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- ZMCHBSMFKQYNKA-UHFFFAOYSA-N 2-aminobenzenesulfonic acid Chemical compound NC1=CC=CC=C1S(O)(=O)=O ZMCHBSMFKQYNKA-UHFFFAOYSA-N 0.000 description 1
- JJSRGUCTMZWMHY-UHFFFAOYSA-N 2-aminobenzenesulfonic acid;4-aminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1.NC1=CC=CC=C1S(O)(=O)=O JJSRGUCTMZWMHY-UHFFFAOYSA-N 0.000 description 1
- JDTUPLBMGDDPJS-UHFFFAOYSA-N 2-methoxy-2-phenylethanol Chemical compound COC(CO)C1=CC=CC=C1 JDTUPLBMGDDPJS-UHFFFAOYSA-N 0.000 description 1
- CGCRIQNPIBHVCQ-UHFFFAOYSA-N 2-methylidenebutanedioyl dichloride Chemical compound ClC(=O)CC(=C)C(Cl)=O CGCRIQNPIBHVCQ-UHFFFAOYSA-N 0.000 description 1
- JOMNTHCQHJPVAZ-UHFFFAOYSA-N 2-methylpiperazine Chemical compound CC1CNCCN1 JOMNTHCQHJPVAZ-UHFFFAOYSA-N 0.000 description 1
- ZAJAQTYSTDTMCU-UHFFFAOYSA-N 3-aminobenzenesulfonic acid Chemical compound NC1=CC=CC(S(O)(=O)=O)=C1 ZAJAQTYSTDTMCU-UHFFFAOYSA-N 0.000 description 1
- ABSXMLODUTXQDJ-UHFFFAOYSA-N 4-(4-sulfophenyl)benzenesulfonic acid Chemical compound C1=CC(S(=O)(=O)O)=CC=C1C1=CC=C(S(O)(=O)=O)C=C1 ABSXMLODUTXQDJ-UHFFFAOYSA-N 0.000 description 1
- HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 description 1
- KPPQQLYIXMUBRE-UHFFFAOYSA-N 4-phenylcyclohexa-2,4-diene-1,1-dicarbonyl chloride Chemical compound C1=CC(C(=O)Cl)(C(Cl)=O)CC=C1C1=CC=CC=C1 KPPQQLYIXMUBRE-UHFFFAOYSA-N 0.000 description 1
- LGDFHDKSYGVKDC-UHFFFAOYSA-N 8-hydroxyquinoline-5-sulfonic acid Chemical compound C1=CN=C2C(O)=CC=C(S(O)(=O)=O)C2=C1 LGDFHDKSYGVKDC-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- XOBKSJJDNFUZPF-UHFFFAOYSA-N Methoxyethane Chemical compound CCOC XOBKSJJDNFUZPF-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- GKXVJHDEWHKBFH-UHFFFAOYSA-N [2-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=CC=C1CN GKXVJHDEWHKBFH-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- PWAXUOGZOSVGBO-UHFFFAOYSA-N adipoyl chloride Chemical compound ClC(=O)CCCCC(Cl)=O PWAXUOGZOSVGBO-UHFFFAOYSA-N 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 239000012300 argon atmosphere Substances 0.000 description 1
- MIAUJDCQDVWHEV-UHFFFAOYSA-N benzene-1,2-disulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1S(O)(=O)=O MIAUJDCQDVWHEV-UHFFFAOYSA-N 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
- WRUAHXANJKHFIL-UHFFFAOYSA-N benzene-1,3-disulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC(S(O)(=O)=O)=C1 WRUAHXANJKHFIL-UHFFFAOYSA-N 0.000 description 1
- OATNQHYJXLHTEW-UHFFFAOYSA-N benzene-1,4-disulfonic acid Chemical compound OS(=O)(=O)C1=CC=C(S(O)(=O)=O)C=C1 OATNQHYJXLHTEW-UHFFFAOYSA-N 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 239000006172 buffering agent Substances 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 238000002144 chemical decomposition reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 229920006037 cross link polymer Polymers 0.000 description 1
- SUSAGCZZQKACKE-UHFFFAOYSA-N cyclobutane-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCC1C(O)=O SUSAGCZZQKACKE-UHFFFAOYSA-N 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 238000012377 drug delivery Methods 0.000 description 1
- 238000005538 encapsulation Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000012527 feed solution Substances 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000009292 forward osmosis Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
- 230000005660 hydrophilic surface Effects 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 238000002715 modification method Methods 0.000 description 1
- 238000006011 modification reaction Methods 0.000 description 1
- VIUHYPPHBQZSPF-UHFFFAOYSA-N naphthalene-1,4-dicarbonyl chloride Chemical compound C1=CC=C2C(C(=O)Cl)=CC=C(C(Cl)=O)C2=C1 VIUHYPPHBQZSPF-UHFFFAOYSA-N 0.000 description 1
- NZZGQZMNFCTNAM-UHFFFAOYSA-N naphthalene-2,6-dicarbonyl chloride Chemical compound C1=C(C(Cl)=O)C=CC2=CC(C(=O)Cl)=CC=C21 NZZGQZMNFCTNAM-UHFFFAOYSA-N 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- YVOFTMXWTWHRBH-UHFFFAOYSA-N pentanedioyl dichloride Chemical compound ClC(=O)CCCC(Cl)=O YVOFTMXWTWHRBH-UHFFFAOYSA-N 0.000 description 1
- 238000005498 polishing Methods 0.000 description 1
- 238000010248 power generation Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 150000003141 primary amines Chemical group 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000003586 protic polar solvent Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- GWHOGODUVLQCEB-UHFFFAOYSA-N pyridine-2,6-dicarbonyl chloride Chemical compound ClC(=O)C1=CC=CC(C(Cl)=O)=N1 GWHOGODUVLQCEB-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 238000009738 saturating Methods 0.000 description 1
- 239000013535 sea water Substances 0.000 description 1
- 150000003335 secondary amines Chemical group 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical class [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical class ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 238000006557 surface reaction Methods 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- MBYLVOKEDDQJDY-UHFFFAOYSA-N tris(2-aminoethyl)amine Chemical compound NCCN(CCN)CCN MBYLVOKEDDQJDY-UHFFFAOYSA-N 0.000 description 1
- 238000000108 ultra-filtration Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Images
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D1/00—Processes for applying liquids or other fluent materials
- B05D1/36—Successively applying liquids or other fluent materials, e.g. without intermediate treatment
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D69/00—Semi-permeable membranes for separation processes or apparatus characterised by their form, structure or properties; Manufacturing processes specially adapted therefor
- B01D69/12—Composite membranes; Ultra-thin membranes
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D69/00—Semi-permeable membranes for separation processes or apparatus characterised by their form, structure or properties; Manufacturing processes specially adapted therefor
- B01D69/12—Composite membranes; Ultra-thin membranes
- B01D69/1213—Laminated layers
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D69/00—Semi-permeable membranes for separation processes or apparatus characterised by their form, structure or properties; Manufacturing processes specially adapted therefor
- B01D69/12—Composite membranes; Ultra-thin membranes
- B01D69/125—In situ manufacturing by polymerisation, polycondensation, cross-linking or chemical reaction
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D69/00—Semi-permeable membranes for separation processes or apparatus characterised by their form, structure or properties; Manufacturing processes specially adapted therefor
- B01D69/12—Composite membranes; Ultra-thin membranes
- B01D69/125—In situ manufacturing by polymerisation, polycondensation, cross-linking or chemical reaction
- B01D69/1251—In situ manufacturing by polymerisation, polycondensation, cross-linking or chemical reaction by interfacial polymerisation
-
- 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
- B01D71/56—Polyamides, e.g. polyester-amides
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M8/00—Fuel cells; Manufacture thereof
- H01M8/10—Fuel cells with solid electrolytes
- H01M8/1009—Fuel cells with solid electrolytes with one of the reactants being liquid, solid or liquid-charged
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M8/00—Fuel cells; Manufacture thereof
- H01M8/10—Fuel cells with solid electrolytes
- H01M8/1016—Fuel cells with solid electrolytes characterised by the electrolyte material
- H01M8/1018—Polymeric electrolyte materials
- H01M8/1039—Polymeric electrolyte materials halogenated, e.g. sulfonated polyvinylidene fluorides
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M8/00—Fuel cells; Manufacture thereof
- H01M8/10—Fuel cells with solid electrolytes
- H01M8/1016—Fuel cells with solid electrolytes characterised by the electrolyte material
- H01M8/1018—Polymeric electrolyte materials
- H01M8/1069—Polymeric electrolyte materials characterised by the manufacturing processes
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M8/00—Fuel cells; Manufacture thereof
- H01M8/10—Fuel cells with solid electrolytes
- H01M8/1016—Fuel cells with solid electrolytes characterised by the electrolyte material
- H01M8/1018—Polymeric electrolyte materials
- H01M8/1069—Polymeric electrolyte materials characterised by the manufacturing processes
- H01M8/1072—Polymeric electrolyte materials characterised by the manufacturing processes by chemical reactions, e.g. insitu polymerisation or insitu crosslinking
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D2325/00—Details relating to properties of membranes
- B01D2325/14—Membrane materials having negatively charged functional groups
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A20/00—Water conservation; Efficient water supply; Efficient water use
- Y02A20/124—Water desalination
- Y02A20/131—Reverse-osmosis
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E60/00—Enabling technologies; Technologies with a potential or indirect contribution to GHG emissions mitigation
- Y02E60/30—Hydrogen technology
- Y02E60/50—Fuel cells
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P70/00—Climate change mitigation technologies in the production process for final industrial or consumer products
- Y02P70/50—Manufacturing or production processes characterised by the final manufactured product
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/249921—Web or sheet containing structurally defined element or component
- Y10T428/249953—Composite having voids in a component [e.g., porous, cellular, etc.]
- Y10T428/249981—Plural void-containing components
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Manufacturing & Machinery (AREA)
- General Chemical & Material Sciences (AREA)
- Sustainable Energy (AREA)
- Sustainable Development (AREA)
- Life Sciences & Earth Sciences (AREA)
- Electrochemistry (AREA)
- Separation Using Semi-Permeable Membranes (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Manufacture Of Macromolecular Shaped Articles (AREA)
- Manufacture Of Porous Articles, And Recovery And Treatment Of Waste Products (AREA)
Description
選択層が元の位置に形成されるので上面障壁層及び底面多孔性其の化学的性質及び性能が独立的に研究されることができて、また全体メンブレインの性能を最大化するように最適化されることができるという点で、複合材メンブレインは単一材料の非対称メンブレインに比べて、利点を持つ。薄膜複合材逆浸透(TFC RO)メンブレインは他の類型の逆浸透(RO)メンブレインに比べて高い流量及び高い選択性という適合性を提供することから、市場における優位性をもつこととなった。現在、大部分の商用薄膜複合材逆浸透(TFC RO)メンブレインはポリアミド薄膜に基づく。
好ましい実施形態で、多孔性ポリスルホン支持体はm-フェニレンディアミン水溶液でコーティングされる。コーティングされた支持体から過剰のm-フェニレンディアミン溶液の除去後、このコーティングされた支持体はフレオン(FREON;trichlorotrifluoroethane)に溶解された塩化トリメソイルクロリド(TMC)で被覆される。
A)ポリスルホン多孔性支持体を提供するステップ、
B)前記支持体が水性溶液を備えるアミンによって、基本的に充填されるように水性溶液を備えるアミンをコーティング、浸漬または提供するステップ、
C)溶液を備えるハロゲン化物として、水溶性ではないハロゲン化物溶液をアミン含有支持体に塗布するステップ。
1つの様態から見れば、本発明は薄膜複合材の製造工程を提供するものであり、その方法は、下記工程:
(I)不活性溶媒内に2以上の酸ハロゲン化物基を持つ少なくとも1つの多官能性ハロゲン化アシルを備える第1液状を多孔性支持体の一面または両面に塗布するステップ;及びその後
(II)少なくとも2つのアミン官能基を持つ少なくとも1つの多官能性アミンを備える第2液状で前記多孔性支持体の一面または両面に接触させて、薄膜複合材を形成するステップ;及び
(III)前記形成された複合材を親水性または疎水性の不活性溶媒内でハロゲン化アシルの第3溶液と任意に反応させるステップとを含む。
本明細書で薄膜複合材という用語は多官能性ハロゲン化アシルと多官能性アミノ化合物の界面重合反応によって形成される薄膜が上面に支持されている多孔性支持体の調合体を定義するために使われる。形成される膜はこの化合物の速い反応速度及びこの化合物の形成された膜を通した遅い拡散速度によって本質的に非常に薄い。
本発明で使用される多孔性支持体は微細多孔性支持体なのが好ましい。一般的にこの支持体は十分な速度で透過水(Permeate)の通過を許す気孔サイズを持つ重合体材料で形成される。 しかし、多孔性支持体は気孔のサイズが大きすぎて、メンブレインがその使い先の圧力に耐えられない程度で大きいサイズの気孔を持ってはいけない。作動圧力は選択される工程に依存して、例をあげれば、圧力遅延浸透(PRO)でメンブレインは逆浸透でより大きい気孔を持つことができる。気孔が大きすぎると、薄膜はその高い圧力によって破裂される。実際面で、圧力遅延浸透(PRO)工程のための支持体メンブレインは逆浸透(RO)のためのメンブレインよりだいぶ大きい気孔を持つことができる。また、気孔が大きすぎると、溶媒は気孔の構造内で固定化(immobilized)されない。支持体の気孔のサイズは一般的に1ないし100nmの範囲である。
支持体構造は、不活性溶媒、好ましくは非プロトン性溶媒に少なくとも一つの多官能性ハロゲン化アシルの溶液を含む第1液相によって湿潤される。ここで使用している湿潤という用語は第一液相を適用することを意味するために、それは圧力かけずに、前記液相が支持体の細孔に入ることを意味する。好ましくは、第一の液相が 支持体の細孔に完全に入る、すなわち支持体の細孔を飽和させるように適用される。使用されえる溶媒はジメチルスルホキシド(DMSO)、ジメチルホルムアミド(DMF)、ジメチルエーテル、ジーエチルエーテル、エチルメチルーエーテルと前述したタイプの溶媒の混合物である。
ハロゲン化アシルが応用されてから、多官能性アミンが好ましくは溶媒に応用される。使用され得る溶媒はジメチルスルホキシド(DMSO), ジメチルホルムアミド (DMF), ジメチル・エーテル, ジエチルエーテル、ならびに 水 及び、前述したタイプの溶媒の混合物である。本発明の好ましい第2溶媒は特にジエチレングリコールジメチルエーテル(Diglyme) とエチレングリコールジエチルエーテル(EGDME)とによって例示されるようにグリコールからなるメチルエテールと水である。
逆のプロセスにより、浸透プロセスにおいてより高い水フラックスとより高い塩の保持( 塩類貯留(salt retention))を与えるシステムを非常に簡単に操作することができる。
材料
アルドリッチからMDA(1)、PDA(2)と TMC(3)を、メルク社 からカンファースルホン酸(CSA)とトリエチルアミン(TEA)を用いた。分解を低減するために使用した後にMDAとTMCの瓶をアルゴンガスで詰めている。溶媒として使用されるエチレングリコールジエチルエーテルを無水A1203のカラム上で乾燥させ、活性化モレキュラーシーブ(4Å)上で保存した。アルファ・ラバルから再生セルロースアセテート(RCA)は、すべての実施例において多孔質支持体として使用した。
RCAの膜は(>12時間)一晩エチレングリコールジエチルエーテル(EGDE)に浸漬した。膜はEGDEでTMCの溶液中で一定時間(30秒〜120秒)に浸漬した。メンブレン上の過剰の溶媒をティッシュペーパーやゴムローラーを用いて除去した。膜は、一定時間(30分〜90分)をアルゴン雰囲気下または減圧下で乾燥させた。 MDA(またはPDA)の溶液を、水のCSAおよびTEAを調製し、膜は90秒〜30秒浸漬した。過剰の溶媒をティッシュペーパーやゴムローラーにより除去し、膜は、c-ヘキサンでTMCの溶液中に浸漬した。膜は、乾燥させ(30分〜1時間)とストレージのために水に浸した空気だった。
Claims (19)
- 薄膜複合材の製造方法であって、
(I)親水性多孔性支持体に第1液相を付与し、及び、その後に、
(II)第2液体相を前記親水性多孔性支持体に接触させることを含んでなり、
前記第1液相が、不活性親水性溶媒に、2つ以上の酸ハロゲン化物基を有する少なくとも1つの多官能性ハロゲン化アシルを含んでなるものであり、
前記第2液体相が、少なくとも2つのアミン官能基を有する少なくとも1つの多官能性アミンを含んでなるものである、薄膜複合材の製造方法。 - 前記第1液相および前記第2液相が、混和性である、請求項1に記載の製造方法。
- 前記第1液相および前記第2液相に用いられている溶媒が同一である、請求項1に記載の製造方法。
- 前記支持体が、セルロース支持体である、請求項1に記載の製造方法。
- 前記セルロース支持体が、セルロースアセテートまたは再生セルロースアセテートである、請求項4に記載の製造方法。
- 前記ステップ(I)におけるハロゲン化アシルのうちの少なくとも1つが少なくとも3つの官能基を有するものである、請求項1に記載の製造方法。
- 前記ステップ(II)におけるアミンのうちの少なくとも1つが少なくとも3つの官能基を有するものである、請求項1に記載の製造方法。
- (III)形成された薄膜を第3液相により後処理し、前記薄膜複合材を形成してなることをさらに含んでなり、
前記第3液相が、親水性又は疎水性である不活性溶媒に、2つ以上の酸ハロゲン化物基を有する少なくとも1つの多官能性ハロゲン化アシルを含んでなるものである、請求項1に記載の製造方法。 - 前記ステップ(I)及び前記ステップ(III)におけるハロゲン化アシルのうちの少なくとも1つが、又は、前記ステップ(II)におけるアミンのうちの少なくとも1つが、少なくとも3つの官能基を有するものである、請求項8に記載の製造方法。
- 前記親水性多孔性支持体が、該表面において、−OH、−NH2及び/又は−NHから選択されたプロトン性基を有する場合、親水性多孔性支持体とハロゲン化アシルとの反応が、共有結合を形成するものである、請求項1〜9の何れか一項に記載の製造方法。
- 前記多官能性ハロゲン化アシルが、少なくとも2つの酸ハロゲン化物基を有するものであり、及び/又は、
塩化トリメソイルクロリド、シクロヘキサン−I−1,3,5−トリカルボニルクロリドと3,3,5,5−テトラ塩化ビフェニルからなる群から選択されるものである、請求項1〜10の何れか一項に記載の製造方法。 - 前記多官能性アミンが、少なくとも2つのアミン官能基を有するものであり、及び/又は、
m−フェニレンジアミン、p−フェニレンジアミン、1,3,5−トリアミノベンゼンと1,3,4−トリアミノベンゼンからなる群から選択されてなるものである、請求項1〜11の何れか一項に記載の製造方法。 - 前記第1液相及び/又は第2液相及び/又は第3液相が、ジグライム、エチレングリコールジエチルエーテル又はエチレングリコールジエチルエーテルを含んでなる、請求項1〜12の何れか一項に記載の製造方法。
- 前記第2液相が、水、アルカン又は灯油である、請求項1〜13の何れか一項に記載の製造方法。
- 前記第3液相が、アルカン又は灯油である、請求項6に記載の製造方法。
- イオン性基が、前記薄膜複合材の表面に存在してなる、請求項1〜15の何れか一項に記載の製造方法。
- 浸透方法、ガス分離、ナノフィルトレーション、逆電気透析と及び/又は燃料電池における、請求項1〜16の何れか一項に記載の製造方法により得られた、薄膜複合材の使用。
- 請求項1〜16の何れか一項に記載の製造方法により得られた薄膜複合材を介して水を通過させることを含んでなる、淡水化方法。
- 請求項1〜16の何れか一項に記載の製造方法により得られた薄膜複合材を介して水を通過させることを含んでなる、電力生産のための水の加圧方法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
NO20100814A NO335286B1 (no) | 2010-06-04 | 2010-06-04 | Tynnfilmkompositter |
NO20100814 | 2010-06-04 | ||
PCT/NO2011/000162 WO2011152735A1 (en) | 2010-06-04 | 2011-05-31 | Thin film composites |
Publications (3)
Publication Number | Publication Date |
---|---|
JP2013528488A JP2013528488A (ja) | 2013-07-11 |
JP2013528488A5 JP2013528488A5 (ja) | 2014-07-17 |
JP5964292B2 true JP5964292B2 (ja) | 2016-08-03 |
Family
ID=45066947
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2013513129A Expired - Fee Related JP5964292B2 (ja) | 2010-06-04 | 2011-05-31 | 薄膜複合材 |
Country Status (6)
Country | Link |
---|---|
US (1) | US20130089727A1 (ja) |
EP (1) | EP2576027B1 (ja) |
JP (1) | JP5964292B2 (ja) |
CA (1) | CA2801638C (ja) |
NO (1) | NO335286B1 (ja) |
WO (1) | WO2011152735A1 (ja) |
Families Citing this family (24)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP6018790B2 (ja) * | 2011-07-22 | 2016-11-02 | 三星電子株式会社Samsung Electronics Co.,Ltd. | 分離膜、この製造方法および分離膜を含む水処理装置 |
WO2013032586A1 (en) | 2011-08-31 | 2013-03-07 | Dow Global Technologies Llc | Composite polyamide membrane derived from monomer including amine-reactive and phosphorous-containing functional groups |
WO2013048764A1 (en) | 2011-09-29 | 2013-04-04 | Dow Global Technologies Llc | Method for preparing high purity mono-hydrolyzed acyl halide compound |
WO2013103666A1 (en) | 2012-01-06 | 2013-07-11 | Dow Global Technologies Llc | Composite polyamide membrane |
EP2874733A1 (en) | 2012-07-19 | 2015-05-27 | Dow Global Technologies LLC | Composite polyamide membrane with increased carboxylic acid functionality |
WO2014109947A1 (en) | 2013-01-14 | 2014-07-17 | Dow Global Technologies Llc | Composite polyamide membrane comprising substituted benzamide monomer |
WO2014109946A1 (en) | 2013-01-14 | 2014-07-17 | Dow Global Technologies Llc | Composite polyamide membrane |
US9289729B2 (en) | 2013-03-16 | 2016-03-22 | Dow Global Technologies Llc | Composite polyamide membrane derived from carboxylic acid containing acyl halide monomer |
US9051417B2 (en) | 2013-03-16 | 2015-06-09 | Dow Global Technologies Llc | Method for solubilizing carboxylic acid-containing compound in hydrocarbon solvent |
CN105163837B (zh) | 2013-05-03 | 2017-05-10 | 陶氏环球技术有限责任公司 | 衍生自脂肪族非环状叔胺化合物的复合聚酰胺膜 |
US9452391B1 (en) | 2013-12-02 | 2016-09-27 | Dow Global Technologies Llc | Composite polyamide membrane treated with dihyroxyaryl compounds and nitrous acid |
ES2659569T3 (es) | 2013-12-02 | 2018-03-16 | Dow Global Technologies Llc | Método para formar una membrana de poliamida compuesta con tratamiento posterior de ácido nitroso |
KR102273550B1 (ko) | 2014-01-09 | 2021-07-07 | 다우 글로벌 테크놀로지스 엘엘씨 | 아조 함량 및 높은 산 함량을 갖는 복합 폴리아미드 막 |
EP3092062B1 (en) | 2014-01-09 | 2018-05-30 | Dow Global Technologies LLC | Composite polyamide membrane having preferred azo content |
CN105873666B (zh) | 2014-01-09 | 2019-11-01 | 陶氏环球技术有限责任公司 | 具有高酸含量和低偶氮含量的复合聚酰胺膜 |
CN106257977B (zh) | 2014-04-28 | 2019-10-29 | 陶氏环球技术有限责任公司 | 用亚硝酸后处理的复合聚酰胺膜 |
WO2015175258A1 (en) | 2014-05-14 | 2015-11-19 | Dow Global Technologies Llc | Composite polyamide membrane post-treated with nitrous acid |
WO2018164585A1 (en) | 2017-03-09 | 2018-09-13 | Nilsen Tom Nils | Hydrophilic tfc membranes and a process for the preparation of such membranes |
NO20170560A1 (en) * | 2017-04-05 | 2018-10-08 | Nilsen Tom Nils | TFC membranes and a process for the preparation of such membranes |
CN112448008B (zh) * | 2019-08-28 | 2022-07-26 | 中国科学院大连化学物理研究所 | 一种具有超薄功能层的液流电池用复合膜及其制备与应用 |
US11613614B2 (en) * | 2020-03-19 | 2023-03-28 | 86 Solar Inc. | Lazarev reactor 1 : production of films of two-dimensional polymers |
CN113401961B (zh) * | 2021-05-20 | 2023-06-23 | 陈鹏 | 一种可光谱调控的水处理用黑色素材料及其制备方法 |
KR102612070B1 (ko) * | 2021-07-28 | 2023-12-07 | 인천대학교 산학협력단 | 폴리아미드 층이 코팅된 나피온 복합체 분리막 및 이의 제조방법 |
CN115090124B (zh) * | 2022-07-01 | 2023-09-05 | 浙江理工大学 | 一种界面聚合反应生成双电荷层复合膜的制备方法及应用 |
Family Cites Families (20)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4039440A (en) | 1972-09-19 | 1977-08-02 | The United States Of America As Represented By The Secretary Of The Interior | Reverse osmosis membrane |
US3906250A (en) | 1973-07-03 | 1975-09-16 | Univ Ben Gurion | Method and apparatus for generating power utilizing pressure-retarded-osmosis |
IL51541A (en) | 1977-02-25 | 1979-05-31 | Univ Ben Gurion | Method and apparatus for generating power utilizing pressuure retarded osmosis |
US4277344A (en) | 1979-02-22 | 1981-07-07 | Filmtec Corporation | Interfacially synthesized reverse osmosis membrane |
US4606943A (en) * | 1983-03-18 | 1986-08-19 | Culligan International Company | Method for preparation of semipermeable composite membrane |
EP0313354A1 (en) * | 1987-10-23 | 1989-04-26 | Pci Membrane Systems Limited | Reverse osmosis membranes and process for their production |
US5049167A (en) | 1989-12-13 | 1991-09-17 | Membrane Technology & Research, Inc. | Multilayer interfacial composite membrane |
JP2885878B2 (ja) * | 1990-05-14 | 1999-04-26 | 株式会社トクヤマ | 分離膜 |
US5234598A (en) * | 1992-05-13 | 1993-08-10 | Allied-Signal Inc. | Thin-film composite membrane |
JPH07178327A (ja) * | 1993-11-12 | 1995-07-18 | Nitto Denko Corp | 複合半透膜及びその製造方法 |
US5614099A (en) * | 1994-12-22 | 1997-03-25 | Nitto Denko Corporation | Highly permeable composite reverse osmosis membrane, method of producing the same, and method of using the same |
US5582725A (en) * | 1995-05-19 | 1996-12-10 | Bend Research, Inc. | Chlorine-resistant composite membranes with high organic rejection |
JP4176846B2 (ja) * | 1996-01-24 | 2008-11-05 | 日東電工株式会社 | 高透過性複合逆浸透膜の製造方法 |
US6048383A (en) * | 1998-10-08 | 2000-04-11 | International Fuel Cells, L.L.C. | Mass transfer composite membrane for a fuel cell power plant |
US6337018B1 (en) * | 2000-04-17 | 2002-01-08 | The Dow Chemical Company | Composite membrane and method for making the same |
US7279097B2 (en) * | 2003-06-18 | 2007-10-09 | Toray Industries, Inc. | Composite semipermeable membrane, and production process thereof |
JP3935114B2 (ja) | 2003-06-20 | 2007-06-20 | 本田技研工業株式会社 | 車両用パワープラントのマウント装置 |
KR100716210B1 (ko) * | 2005-09-20 | 2007-05-10 | 웅진코웨이주식회사 | 폴리아미드 역삼투 복합막 제조방법 및 이로부터 제조된폴리아미드 역삼투 복합막 |
US8196754B2 (en) * | 2007-01-17 | 2012-06-12 | The Ohio States University Research Foundation | Water permeable membranes and methods of making water permeable membranes |
US9010547B2 (en) * | 2007-05-26 | 2015-04-21 | The Research Foundation Of State University Of New York | High flux fluid separation membranes comprising a cellulose or cellulose derivative layer |
-
2010
- 2010-06-04 NO NO20100814A patent/NO335286B1/no not_active IP Right Cessation
-
2011
- 2011-05-31 WO PCT/NO2011/000162 patent/WO2011152735A1/en active Application Filing
- 2011-05-31 US US13/701,520 patent/US20130089727A1/en not_active Abandoned
- 2011-05-31 JP JP2013513129A patent/JP5964292B2/ja not_active Expired - Fee Related
- 2011-05-31 EP EP11790058.9A patent/EP2576027B1/en active Active
- 2011-05-31 CA CA2801638A patent/CA2801638C/en not_active Expired - Fee Related
Also Published As
Publication number | Publication date |
---|---|
EP2576027A1 (en) | 2013-04-10 |
EP2576027B1 (en) | 2020-08-26 |
EP2576027A4 (en) | 2016-10-05 |
JP2013528488A (ja) | 2013-07-11 |
CA2801638C (en) | 2020-03-24 |
NO335286B1 (no) | 2014-11-03 |
NO20100814A1 (no) | 2011-12-05 |
WO2011152735A1 (en) | 2011-12-08 |
CA2801638A1 (en) | 2011-12-08 |
US20130089727A1 (en) | 2013-04-11 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP5964292B2 (ja) | 薄膜複合材 | |
US8196754B2 (en) | Water permeable membranes and methods of making water permeable membranes | |
KR102155533B1 (ko) | 복합 반투막 및 그 제조 방법 | |
Yu et al. | Performance enhancement in interfacially synthesized thin-film composite polyamide-urethane reverse osmosis membrane for seawater desalination | |
US8733558B2 (en) | Composite membrane with coating comprising polyalkylene oxide and biguanide-type compounds | |
US10898857B2 (en) | Membranes with alternative selective layers | |
US8646617B2 (en) | Reverse osmosis membrane having good antifouling properties and method of manufacturing the same | |
EP1806174B1 (en) | Process for producing semipermeable composite membrane | |
JP2016531738A (ja) | 耐久性に優れたポリアミド系水処理分離膜およびその製造方法 | |
US20230060093A1 (en) | High-flux water permeable membranes | |
JP2005505406A (ja) | 複合ナノ濾過膜および逆浸透膜ならびにこれを生成するための方法 | |
JPH0810595A (ja) | 複合逆浸透膜 | |
KR101114668B1 (ko) | 폴리아마이드 역삼투 분리막의 제조방법 및 그에 의해 제조된 폴리아마이드 역삼투 분리막 | |
CN110841494A (zh) | 一种两性复合正渗透膜及其制备方法和应用 | |
KR20060051998A (ko) | 역삼투막 및 그의 제조 방법 | |
JP5877855B2 (ja) | 有機単量体間の架橋を利用した多層薄膜基盤の逆浸透分離膜及びその製造方法 | |
KR20170061662A (ko) | 복합 반투막 및 그 제조 방법, 및 스파이럴형 분리막 엘리먼트 | |
Trivedi et al. | Alkyl amine functional dextran macromonomer‐based thin film composite loose nanofiltration membranes for separation of charged and neutral solutes | |
WO2007084921A2 (en) | Water permeable membranes and methods of making water permeable membranes | |
NO20170560A1 (en) | TFC membranes and a process for the preparation of such membranes | |
KR102045108B1 (ko) | 역삼투막 및 그 제조방법 | |
JPH0910565A (ja) | 半透性複合膜 | |
JP2007125544A5 (ja) | ||
JP2002095940A (ja) | 複合逆浸透膜とその製造方法及びその使用方法 | |
KR101716045B1 (ko) | 투과유량 특성이 우수한 폴리아미드계 수처리 분리막의 제조 방법 및 상기 제조 방법으로 제조된 수처리 분리막 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20140602 |
|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20140602 |
|
A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20150219 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20150303 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20150601 |
|
A02 | Decision of refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A02 Effective date: 20151104 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20160304 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A821 Effective date: 20160414 |
|
A911 | Transfer to examiner for re-examination before appeal (zenchi) |
Free format text: JAPANESE INTERMEDIATE CODE: A911 Effective date: 20160516 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20160531 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20160629 |
|
R150 | Certificate of patent or registration of utility model |
Ref document number: 5964292 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
LAPS | Cancellation because of no payment of annual fees |