JPH0278428A - 複合半透膜およびその製造方法 - Google Patents
複合半透膜およびその製造方法Info
- Publication number
- JPH0278428A JPH0278428A JP63265068A JP26506888A JPH0278428A JP H0278428 A JPH0278428 A JP H0278428A JP 63265068 A JP63265068 A JP 63265068A JP 26506888 A JP26506888 A JP 26506888A JP H0278428 A JPH0278428 A JP H0278428A
- Authority
- JP
- Japan
- Prior art keywords
- weight
- ethylenediamine
- piperazine
- membrane
- polyamide
- 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 92
- 238000004519 manufacturing process Methods 0.000 title claims description 13
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims abstract description 80
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims abstract description 38
- 239000004952 Polyamide Substances 0.000 claims abstract description 31
- 229920002647 polyamide Polymers 0.000 claims abstract description 31
- 239000002253 acid Substances 0.000 claims abstract description 23
- 150000004820 halides Chemical class 0.000 claims abstract description 23
- 125000001624 naphthyl group Chemical group 0.000 claims abstract description 6
- 229920006037 cross link polymer Polymers 0.000 claims abstract description 5
- 238000006068 polycondensation reaction Methods 0.000 claims abstract description 5
- 239000000126 substance Substances 0.000 claims abstract description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 52
- 239000002131 composite material Substances 0.000 claims description 23
- 239000000243 solution Substances 0.000 claims description 23
- 239000007864 aqueous solution Substances 0.000 claims description 22
- 150000003839 salts Chemical class 0.000 claims description 14
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 10
- 125000003916 ethylene diamine group Chemical group 0.000 claims description 6
- 125000004193 piperazinyl group Chemical group 0.000 claims description 6
- 239000011780 sodium chloride Substances 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 230000008030 elimination Effects 0.000 claims description 2
- 238000003379 elimination reaction Methods 0.000 claims description 2
- 230000001747 exhibiting effect Effects 0.000 claims description 2
- 239000011248 coating agent Substances 0.000 abstract description 3
- 238000000576 coating method Methods 0.000 abstract description 3
- 230000001588 bifunctional effect Effects 0.000 abstract description 2
- 239000003344 environmental pollutant Substances 0.000 abstract description 2
- 231100000719 pollutant Toxicity 0.000 abstract description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- 239000000203 mixture Substances 0.000 description 19
- 238000012360 testing method Methods 0.000 description 19
- 238000010612 desalination reaction Methods 0.000 description 17
- 238000001223 reverse osmosis Methods 0.000 description 17
- 235000002639 sodium chloride Nutrition 0.000 description 17
- 150000001412 amines Chemical class 0.000 description 15
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- 239000010408 film Substances 0.000 description 11
- ZIWRUEGECALFST-UHFFFAOYSA-M sodium 4-(4-dodecoxysulfonylphenoxy)benzenesulfonate Chemical compound [Na+].CCCCCCCCCCCCOS(=O)(=O)c1ccc(Oc2ccc(cc2)S([O-])(=O)=O)cc1 ZIWRUEGECALFST-UHFFFAOYSA-M 0.000 description 11
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 9
- 239000000460 chlorine Substances 0.000 description 9
- 229910052801 chlorine Inorganic materials 0.000 description 9
- 239000001488 sodium phosphate Substances 0.000 description 9
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 9
- 229910000406 trisodium phosphate Inorganic materials 0.000 description 9
- 235000019801 trisodium phosphate Nutrition 0.000 description 9
- 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 8
- 238000000034 method Methods 0.000 description 8
- -1 trimesic acid halide Chemical class 0.000 description 8
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 6
- 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 6
- 230000035699 permeability Effects 0.000 description 5
- 229920002492 poly(sulfone) Polymers 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 4
- 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 4
- 230000000052 comparative effect Effects 0.000 description 4
- 239000000470 constituent Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000011148 porous material Substances 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000005520 cutting process Methods 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000010409 thin film Substances 0.000 description 3
- 239000002351 wastewater Substances 0.000 description 3
- 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 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 238000012696 Interfacial polycondensation Methods 0.000 description 2
- 239000005708 Sodium hypochlorite Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 230000006866 deterioration Effects 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 230000007717 exclusion Effects 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 239000004065 semiconductor Substances 0.000 description 2
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 2
- 229910021642 ultra pure water Inorganic materials 0.000 description 2
- 239000012498 ultrapure water Substances 0.000 description 2
- KGRVJHAUYBGFFP-UHFFFAOYSA-N 2,2'-Methylenebis(4-methyl-6-tert-butylphenol) Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O KGRVJHAUYBGFFP-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
- 239000004472 Lysine Substances 0.000 description 1
- 239000000020 Nitrocellulose Substances 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- FJWGYAHXMCUOOM-QHOUIDNNSA-N [(2s,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6s)-4,5-dinitrooxy-2-(nitrooxymethyl)-6-[(2r,3r,4s,5r,6s)-4,5,6-trinitrooxy-2-(nitrooxymethyl)oxan-3-yl]oxyoxan-3-yl]oxy-3,5-dinitrooxy-6-(nitrooxymethyl)oxan-4-yl] nitrate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](O[N+]([O-])=O)[C@H]1O[N+]([O-])=O)O[C@H]1[C@@H]([C@@H](O[N+]([O-])=O)[C@H](O[N+]([O-])=O)[C@@H](CO[N+]([O-])=O)O1)O[N+]([O-])=O)CO[N+](=O)[O-])[C@@H]1[C@@H](CO[N+]([O-])=O)O[C@@H](O[N+]([O-])=O)[C@H](O[N+]([O-])=O)[C@H]1O[N+]([O-])=O FJWGYAHXMCUOOM-QHOUIDNNSA-N 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- KKEYFWRCBNTPAC-UHFFFAOYSA-N benzene-dicarboxylic acid Natural products OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- 238000005345 coagulation Methods 0.000 description 1
- 230000015271 coagulation Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000004070 electrodeposition Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 229920001220 nitrocellulos Polymers 0.000 description 1
- 239000005416 organic matter Substances 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- WEYVCQFUGFRXOM-UHFFFAOYSA-N perazine Chemical compound C1CN(C)CCN1CCCN1C2=CC=CC=C2SC2=CC=CC=C21 WEYVCQFUGFRXOM-UHFFFAOYSA-N 0.000 description 1
- 229960002195 perazine Drugs 0.000 description 1
- QQVIHTHCMHWDBS-UHFFFAOYSA-N perisophthalic acid Natural products OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 230000001568 sexual effect Effects 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- HIEHAIZHJZLEPQ-UHFFFAOYSA-M sodium;naphthalene-1-sulfonate Chemical compound [Na+].C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1 HIEHAIZHJZLEPQ-UHFFFAOYSA-M 0.000 description 1
- LXEJRKJRKIFVNY-UHFFFAOYSA-N terephthaloyl chloride Chemical compound ClC(=O)C1=CC=C(C(Cl)=O)C=C1 LXEJRKJRKIFVNY-UHFFFAOYSA-N 0.000 description 1
- QMKYBPDZANOJGF-UHFFFAOYSA-N trimesic acid Natural products OC(=O)C1=CC(C(O)=O)=CC(C(O)=O)=C1 QMKYBPDZANOJGF-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000009941 weaving Methods 0.000 description 1
Landscapes
- Separation Using Semi-Permeable Membranes (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63265068A JPH0278428A (ja) | 1988-06-07 | 1988-10-20 | 複合半透膜およびその製造方法 |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63-140081 | 1988-06-07 | ||
| JP14008188 | 1988-06-07 | ||
| JP63265068A JPH0278428A (ja) | 1988-06-07 | 1988-10-20 | 複合半透膜およびその製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH0278428A true JPH0278428A (ja) | 1990-03-19 |
| JPH0565213B2 JPH0565213B2 (enrdf_load_stackoverflow) | 1993-09-17 |
Family
ID=15260519
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP63265068A Granted JPH0278428A (ja) | 1988-06-07 | 1988-10-20 | 複合半透膜およびその製造方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0278428A (enrdf_load_stackoverflow) |
Cited By (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0465649A4 (en) * | 1990-01-26 | 1992-07-01 | Toray Industries, Inc. | Composite semipermeable membrane and production thereof |
| WO2006038503A1 (ja) * | 2004-10-04 | 2006-04-13 | Nitto Denko Corporation | 複合逆浸透膜の製造方法 |
| EP2014350A2 (en) | 2001-03-19 | 2009-01-14 | Nitto Denko Corporation | Water-treating method |
| WO2011078131A1 (ja) | 2009-12-22 | 2011-06-30 | 東レ株式会社 | 半透膜およびその製造方法 |
| WO2011105278A1 (ja) | 2010-02-23 | 2011-09-01 | 東レ株式会社 | 複合半透膜およびその製造方法 |
| WO2012020680A1 (ja) | 2010-08-11 | 2012-02-16 | 東レ株式会社 | 分離膜エレメントおよび複合半透膜の製造方法 |
| WO2012090862A1 (ja) | 2010-12-28 | 2012-07-05 | 東レ株式会社 | 複合半透膜 |
| WO2012137635A1 (ja) | 2011-04-01 | 2012-10-11 | 東レ株式会社 | 複合半透膜、複合半透膜エレメントおよび複合半透膜の製造方法 |
| WO2013108788A1 (ja) | 2012-01-16 | 2013-07-25 | 東レ株式会社 | 複合半透膜およびその製造方法 |
| US8518310B2 (en) | 2006-10-10 | 2013-08-27 | Nitto Denko Corporation | Process for producing a dried composite semipermeable membrane |
| WO2013129610A1 (ja) | 2012-02-29 | 2013-09-06 | 東レ株式会社 | 複合半透膜 |
| WO2014003141A1 (ja) | 2012-06-27 | 2014-01-03 | 東レ株式会社 | 複合半透膜 |
| KR20140005918A (ko) * | 2010-12-20 | 2014-01-15 | 제너럴 일렉트릭 캄파니 | 계면 중합에 의한 폴리설폰아마이드 막 |
| WO2014050701A1 (ja) | 2012-09-26 | 2014-04-03 | 東レ株式会社 | 複合半透膜 |
| WO2014133130A1 (ja) | 2013-02-28 | 2014-09-04 | 東レ株式会社 | 複合半透膜およびその製造方法 |
| US8851297B2 (en) | 2006-10-10 | 2014-10-07 | Nitto Denko Corporation | Composite semipermeable membrane and process for producing the same |
| JP2017023957A (ja) * | 2015-07-24 | 2017-02-02 | 日東電工株式会社 | 複合分離膜及び分離膜エレメント |
| WO2017111140A1 (ja) | 2015-12-25 | 2017-06-29 | 東レ株式会社 | 複合半透膜 |
| WO2018143297A1 (ja) | 2017-01-31 | 2018-08-09 | 東レ株式会社 | 複合半透膜及び複合半透膜の製造方法 |
| WO2018221684A1 (ja) | 2017-06-01 | 2018-12-06 | 東レ株式会社 | ガス分離膜、ガス分離膜エレメント、ガス分離装置及びガス分離方法 |
| WO2019131786A1 (ja) | 2017-12-26 | 2019-07-04 | 東レ株式会社 | ガス分離膜、ガス分離膜エレメント及びガス分離方法 |
| WO2019168137A1 (ja) | 2018-02-28 | 2019-09-06 | 東レ株式会社 | 複合半透膜および複合半透膜エレメント |
| WO2019168138A1 (ja) | 2018-02-28 | 2019-09-06 | 東レ株式会社 | 複合半透膜および複合半透膜エレメント |
| WO2021085599A1 (ja) | 2019-10-31 | 2021-05-06 | 東レ株式会社 | 複合半透膜 |
| CN117177806A (zh) * | 2021-04-22 | 2023-12-05 | 东丽株式会社 | 复合半透膜 |
-
1988
- 1988-10-20 JP JP63265068A patent/JPH0278428A/ja active Granted
Cited By (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0465649A4 (en) * | 1990-01-26 | 1992-07-01 | Toray Industries, Inc. | Composite semipermeable membrane and production thereof |
| EP2014350A2 (en) | 2001-03-19 | 2009-01-14 | Nitto Denko Corporation | Water-treating method |
| WO2006038503A1 (ja) * | 2004-10-04 | 2006-04-13 | Nitto Denko Corporation | 複合逆浸透膜の製造方法 |
| JP2006130497A (ja) * | 2004-10-04 | 2006-05-25 | Nitto Denko Corp | 複合逆浸透膜の製造方法 |
| KR100885591B1 (ko) * | 2004-10-04 | 2009-02-24 | 닛토덴코 가부시키가이샤 | 복합 역침투막의 제조 방법 |
| US8851297B2 (en) | 2006-10-10 | 2014-10-07 | Nitto Denko Corporation | Composite semipermeable membrane and process for producing the same |
| US8518310B2 (en) | 2006-10-10 | 2013-08-27 | Nitto Denko Corporation | Process for producing a dried composite semipermeable membrane |
| WO2011078131A1 (ja) | 2009-12-22 | 2011-06-30 | 東レ株式会社 | 半透膜およびその製造方法 |
| WO2011105278A1 (ja) | 2010-02-23 | 2011-09-01 | 東レ株式会社 | 複合半透膜およびその製造方法 |
| WO2012020680A1 (ja) | 2010-08-11 | 2012-02-16 | 東レ株式会社 | 分離膜エレメントおよび複合半透膜の製造方法 |
| KR20140005918A (ko) * | 2010-12-20 | 2014-01-15 | 제너럴 일렉트릭 캄파니 | 계면 중합에 의한 폴리설폰아마이드 막 |
| JP2014501294A (ja) * | 2010-12-20 | 2014-01-20 | ゼネラル・エレクトリック・カンパニイ | 変性スルホンアミドポリマーマトリクス |
| WO2012090862A1 (ja) | 2010-12-28 | 2012-07-05 | 東レ株式会社 | 複合半透膜 |
| WO2012137635A1 (ja) | 2011-04-01 | 2012-10-11 | 東レ株式会社 | 複合半透膜、複合半透膜エレメントおよび複合半透膜の製造方法 |
| WO2013108788A1 (ja) | 2012-01-16 | 2013-07-25 | 東レ株式会社 | 複合半透膜およびその製造方法 |
| WO2013129610A1 (ja) | 2012-02-29 | 2013-09-06 | 東レ株式会社 | 複合半透膜 |
| WO2014003141A1 (ja) | 2012-06-27 | 2014-01-03 | 東レ株式会社 | 複合半透膜 |
| US10974205B2 (en) | 2012-06-27 | 2021-04-13 | Toray Industries, Inc. | Composite semipermeable membrane |
| WO2014050701A1 (ja) | 2012-09-26 | 2014-04-03 | 東レ株式会社 | 複合半透膜 |
| US9827536B2 (en) | 2012-09-26 | 2017-11-28 | Toray Industries, Inc. | Composite semipermeable membrane |
| WO2014133130A1 (ja) | 2013-02-28 | 2014-09-04 | 東レ株式会社 | 複合半透膜およびその製造方法 |
| JP2017023957A (ja) * | 2015-07-24 | 2017-02-02 | 日東電工株式会社 | 複合分離膜及び分離膜エレメント |
| WO2017111140A1 (ja) | 2015-12-25 | 2017-06-29 | 東レ株式会社 | 複合半透膜 |
| WO2018143297A1 (ja) | 2017-01-31 | 2018-08-09 | 東レ株式会社 | 複合半透膜及び複合半透膜の製造方法 |
| WO2018221684A1 (ja) | 2017-06-01 | 2018-12-06 | 東レ株式会社 | ガス分離膜、ガス分離膜エレメント、ガス分離装置及びガス分離方法 |
| WO2019131786A1 (ja) | 2017-12-26 | 2019-07-04 | 東レ株式会社 | ガス分離膜、ガス分離膜エレメント及びガス分離方法 |
| WO2019168137A1 (ja) | 2018-02-28 | 2019-09-06 | 東レ株式会社 | 複合半透膜および複合半透膜エレメント |
| WO2019168138A1 (ja) | 2018-02-28 | 2019-09-06 | 東レ株式会社 | 複合半透膜および複合半透膜エレメント |
| WO2021085599A1 (ja) | 2019-10-31 | 2021-05-06 | 東レ株式会社 | 複合半透膜 |
| KR20220069097A (ko) | 2019-10-31 | 2022-05-26 | 도레이 카부시키가이샤 | 복합 반투막 |
| US12318738B2 (en) | 2019-10-31 | 2025-06-03 | Toray Industries, Inc. | Composite semi-permeable membrane |
| CN117177806A (zh) * | 2021-04-22 | 2023-12-05 | 东丽株式会社 | 复合半透膜 |
| US12138595B2 (en) | 2021-04-22 | 2024-11-12 | Toray Industries, Inc. | Composite semipermeable membrane |
Also Published As
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| JPH0565213B2 (enrdf_load_stackoverflow) | 1993-09-17 |
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