CN102438734B - 对映选择性复合膜的制备方法 - Google Patents
对映选择性复合膜的制备方法 Download PDFInfo
- Publication number
- CN102438734B CN102438734B CN201080022405.5A CN201080022405A CN102438734B CN 102438734 B CN102438734 B CN 102438734B CN 201080022405 A CN201080022405 A CN 201080022405A CN 102438734 B CN102438734 B CN 102438734B
- Authority
- CN
- China
- Prior art keywords
- film
- enantioselectivity
- composite membrane
- amino acid
- solution
- 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
- 239000012528 membrane Substances 0.000 title claims abstract description 66
- 239000002131 composite material Substances 0.000 title claims abstract description 53
- 238000000034 method Methods 0.000 title claims abstract description 40
- 238000002360 preparation method Methods 0.000 title claims abstract description 21
- 150000001413 amino acids Chemical class 0.000 claims abstract description 41
- 239000000203 mixture Substances 0.000 claims abstract description 40
- 238000000926 separation method Methods 0.000 claims abstract description 38
- 239000000243 solution Substances 0.000 claims description 41
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 33
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 31
- 239000007864 aqueous solution Substances 0.000 claims description 28
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 27
- 239000004475 Arginine Substances 0.000 claims description 19
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 claims description 19
- 238000000108 ultra-filtration Methods 0.000 claims description 19
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 15
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical class C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 claims description 15
- 150000001412 amines Chemical class 0.000 claims description 13
- -1 carboxylic acid halides Chemical class 0.000 claims description 12
- 239000011248 coating agent Substances 0.000 claims description 12
- 238000000576 coating method Methods 0.000 claims description 12
- 229920002492 poly(sulfone) Polymers 0.000 claims description 12
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 claims description 10
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 claims description 10
- 239000004472 Lysine Substances 0.000 claims description 10
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 10
- 229940018564 m-phenylenediamine Drugs 0.000 claims description 10
- 238000012360 testing method Methods 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- 229920000642 polymer Polymers 0.000 claims description 9
- 239000008367 deionised water Substances 0.000 claims description 8
- 229910021641 deionized water Inorganic materials 0.000 claims description 8
- 238000010438 heat treatment Methods 0.000 claims description 8
- 239000002033 PVDF binder Substances 0.000 claims description 4
- 239000004952 Polyamide Substances 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 238000004128 high performance liquid chromatography Methods 0.000 claims description 4
- 238000013507 mapping Methods 0.000 claims description 4
- 229920002647 polyamide Polymers 0.000 claims description 4
- 229920002981 polyvinylidene fluoride Polymers 0.000 claims description 4
- 150000003141 primary amines Chemical group 0.000 claims description 4
- 238000001223 reverse osmosis Methods 0.000 claims description 4
- 239000004695 Polyether sulfone Substances 0.000 claims description 3
- 239000007853 buffer solution Substances 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 238000001816 cooling Methods 0.000 claims description 3
- 238000005470 impregnation Methods 0.000 claims description 3
- 229920006393 polyether sulfone Polymers 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 230000006340 racemization Effects 0.000 claims description 2
- 238000009736 wetting Methods 0.000 claims description 2
- 230000003287 optical effect Effects 0.000 abstract description 10
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 abstract description 4
- 239000010408 film Substances 0.000 description 97
- 235000001014 amino acid Nutrition 0.000 description 33
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 18
- 239000007788 liquid Substances 0.000 description 14
- 238000001764 infiltration Methods 0.000 description 11
- 238000005516 engineering process Methods 0.000 description 10
- 230000008595 infiltration Effects 0.000 description 9
- 239000003814 drug Substances 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 238000007605 air drying Methods 0.000 description 6
- 239000003153 chemical reaction reagent Substances 0.000 description 6
- 230000004907 flux Effects 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 238000004483 ATR-FTIR spectroscopy Methods 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 229940079593 drug Drugs 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 238000001228 spectrum Methods 0.000 description 5
- UEJJHQNACJXSKW-UHFFFAOYSA-N 2-(2,6-dioxopiperidin-3-yl)-1H-isoindole-1,3(2H)-dione Chemical compound O=C1C2=CC=CC=C2C(=O)N1C1CCC(=O)NC1=O UEJJHQNACJXSKW-UHFFFAOYSA-N 0.000 description 4
- 230000005526 G1 to G0 transition Effects 0.000 description 4
- 238000000502 dialysis Methods 0.000 description 4
- 239000012530 fluid Substances 0.000 description 4
- 229920006254 polymer film Polymers 0.000 description 4
- AQHHHDLHHXJYJD-UHFFFAOYSA-N propranolol Chemical compound C1=CC=C2C(OCC(O)CNC(C)C)=CC=CC2=C1 AQHHHDLHHXJYJD-UHFFFAOYSA-N 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 238000010408 sweeping Methods 0.000 description 4
- 229960003433 thalidomide Drugs 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 150000003949 imides Chemical group 0.000 description 3
- SGTNSNPWRIOYBX-MHZLTWQESA-N (S)-verapamil Chemical compound C1=C(OC)C(OC)=CC=C1CCN(C)CCC[C@](C#N)(C(C)C)C1=CC=C(OC)C(OC)=C1 SGTNSNPWRIOYBX-MHZLTWQESA-N 0.000 description 2
- KDXKERNSBIXSRK-RXMQYKEDSA-N D-lysine Chemical compound NCCCC[C@@H](N)C(O)=O KDXKERNSBIXSRK-RXMQYKEDSA-N 0.000 description 2
- 238000012695 Interfacial polymerization Methods 0.000 description 2
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 150000001263 acyl chlorides Chemical class 0.000 description 2
- 239000003463 adsorbent Substances 0.000 description 2
- 239000003905 agrochemical Substances 0.000 description 2
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 2
- 238000013459 approach Methods 0.000 description 2
- 230000033228 biological regulation Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- 239000012069 chiral reagent Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 230000007547 defect Effects 0.000 description 2
- 238000007598 dipping method Methods 0.000 description 2
- 238000005194 fractionation Methods 0.000 description 2
- 150000004676 glycans Chemical class 0.000 description 2
- 238000010406 interfacial reaction Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 238000001728 nano-filtration Methods 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 229920001197 polyacetylene Polymers 0.000 description 2
- 229920001282 polysaccharide Polymers 0.000 description 2
- 239000005017 polysaccharide Substances 0.000 description 2
- 229960003712 propranolol Drugs 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- 229940127291 Calcium channel antagonist Drugs 0.000 description 1
- QNAYBMKLOCPYGJ-UWTATZPHSA-N D-alanine Chemical compound C[C@@H](N)C(O)=O QNAYBMKLOCPYGJ-UWTATZPHSA-N 0.000 description 1
- ODKSFYDXXFIFQN-SCSAIBSYSA-N D-arginine Chemical compound OC(=O)[C@H](N)CCCNC(N)=N ODKSFYDXXFIFQN-SCSAIBSYSA-N 0.000 description 1
- 238000012696 Interfacial polycondensation Methods 0.000 description 1
- 108010038807 Oligopeptides Proteins 0.000 description 1
- 102000015636 Oligopeptides Human genes 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 208000031320 Teratogenesis Diseases 0.000 description 1
- 125000000777 acyl halide group Chemical group 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 235000004279 alanine Nutrition 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
- 239000004760 aramid Substances 0.000 description 1
- 229920003235 aromatic polyamide Polymers 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 238000010923 batch production Methods 0.000 description 1
- 238000005452 bending Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000000480 calcium channel blocker Substances 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 230000000747 cardiac effect Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000005557 chiral recognition Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 230000001112 coagulating effect Effects 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- SGTNSNPWRIOYBX-HHHXNRCGSA-N dexverapamil Chemical compound C1=C(OC)C(OC)=CC=C1CCN(C)CCC[C@@](C#N)(C(C)C)C1=CC=C(OC)C(OC)=C1 SGTNSNPWRIOYBX-HHHXNRCGSA-N 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 238000011010 flushing procedure Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 229910052732 germanium Inorganic materials 0.000 description 1
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- WFKAJVHLWXSISD-UHFFFAOYSA-N isobutyramide Chemical compound CC(C)C(N)=O WFKAJVHLWXSISD-UHFFFAOYSA-N 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 235000018977 lysine Nutrition 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229920000344 molecularly imprinted polymer Polymers 0.000 description 1
- QRYWJFOBXFDERP-UHFFFAOYSA-N n-[(2-amino-6-methylpyridin-3-yl)methyl]-3,4,5-trimethoxybenzamide Chemical compound COC1=C(OC)C(OC)=CC(C(=O)NCC=2C(=NC(C)=CC=2)N)=C1 QRYWJFOBXFDERP-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 230000035935 pregnancy Effects 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 235000018102 proteins Nutrition 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000003087 receptor blocking agent Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
Images
Classifications
-
- 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
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D61/00—Processes of separation using semi-permeable membranes, e.g. dialysis, osmosis or ultrafiltration; Apparatus, accessories or auxiliary operations specially adapted therefor
- B01D61/007—Separation by stereostructure, steric separation
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D67/00—Processes specially adapted for manufacturing semi-permeable membranes for separation processes or apparatus
- B01D67/0002—Organic membrane manufacture
-
- 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
- B01D69/02—Semi-permeable membranes for separation processes or apparatus characterised by their form, structure or properties; Manufacturing processes specially adapted therefor characterised by their properties
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/30—Preparation of optical isomers
- C07C227/34—Preparation of optical isomers by separation of optical isomers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C277/00—Preparation of guanidine or its derivatives, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
- C07C277/06—Purification or separation of guanidine
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Analytical Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Water Supply & Treatment (AREA)
- Manufacturing & Machinery (AREA)
- Separation Using Semi-Permeable Membranes (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN629/DEL/2009 | 2009-03-27 | ||
| IN629DE2009 | 2009-03-27 | ||
| PCT/IN2010/000188 WO2010109490A1 (en) | 2009-03-27 | 2010-03-25 | A method for preparation of enantioselective composite membrane |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN102438734A CN102438734A (zh) | 2012-05-02 |
| CN102438734B true CN102438734B (zh) | 2014-05-28 |
Family
ID=42237004
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201080022405.5A Expired - Fee Related CN102438734B (zh) | 2009-03-27 | 2010-03-25 | 对映选择性复合膜的制备方法 |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JP5619867B2 (ko) |
| KR (1) | KR101573968B1 (ko) |
| CN (1) | CN102438734B (ko) |
| DE (1) | DE112010001374T5 (ko) |
| WO (1) | WO2010109490A1 (ko) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102179185A (zh) * | 2011-03-29 | 2011-09-14 | 北京化工大学 | 一种手性拆分固膜的制备方法 |
| US20150005530A1 (en) * | 2012-02-06 | 2015-01-01 | Council Scientific & Industrial Research | L-enantiomers selective membrane for optical resolution of alpha-amino acids and process for the preparation thereof |
| CN103357279B (zh) * | 2013-07-30 | 2015-09-30 | 云南师范大学 | 替考拉宁手性复合膜及其在d,l-对羟基苯甘氨酸外消旋体拆分中的应用 |
| CN104437110B (zh) | 2014-12-15 | 2016-09-28 | 湖南澳维环保科技有限公司 | 一种大通量聚酰胺复合膜 |
| CN107921378A (zh) | 2015-07-31 | 2018-04-17 | 东丽株式会社 | 分离膜、分离膜元件、净水器及分离膜的制造方法 |
| CZ2019178A3 (cs) * | 2019-03-24 | 2020-10-14 | Ústav Chemických Procesů Av Čr, V. V. I. | Kompozitní chirální membrána, způsob její přípravy a způsob obohacování směsí enantiomerů |
| CN110339724B (zh) * | 2019-06-26 | 2021-08-03 | 四川大学 | 一种具有盐浓度响应性复合聚酰胺膜及其制备方法和用途 |
| KR102646731B1 (ko) * | 2021-06-24 | 2024-03-12 | 이화여자대학교 산학협력단 | 블록 공중합체를 이용한 키랄성 나노구조체의 제조 방법 |
| KR20240056167A (ko) | 2022-10-21 | 2024-04-30 | 경희대학교 산학협력단 | 키랄 결정성 물질의 거울상 이성질체 분리 방법 |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2233248A (en) * | 1989-06-07 | 1991-01-09 | Aligena Ag | Enantiomer enrichment by membrane processes |
| US6270640B1 (en) * | 1998-04-29 | 2001-08-07 | Board Of Supervisors Of Louisiana State University And Agricultural And Mechanical College | Polymerized oligopeptide-surfactant chiral micelles |
| CN1772356A (zh) * | 2005-11-02 | 2006-05-17 | 华东理工大学 | 一种手性分子印迹纤维复合膜及其制备方法和应用 |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4277344A (en) | 1979-02-22 | 1981-07-07 | Filmtec Corporation | Interfacially synthesized reverse osmosis membrane |
| JPS60193930A (ja) * | 1984-03-13 | 1985-10-02 | Daicel Chem Ind Ltd | 分離剤 |
| JPH0651789B2 (ja) * | 1985-03-20 | 1994-07-06 | 正木 長谷川 | 光学活性ポリアミド |
| JP2547216B2 (ja) * | 1987-07-08 | 1996-10-23 | ダイセル化学工業株式会社 | 分離剤 |
| US5080795A (en) | 1990-05-23 | 1992-01-14 | Research Corporation Technologies, Inc. | Supported chiral liquid membrane for the separation of enantiomers |
| JP2898723B2 (ja) * | 1990-08-31 | 1999-06-02 | ダイセル化学工業株式会社 | 光学分割分離膜 |
| US5205934A (en) | 1991-08-30 | 1993-04-27 | Membrane Products Kiryat Weitzman Ltd. | Silicone-derived solvent stable membranes |
| JP3170724B2 (ja) * | 1992-03-11 | 2001-05-28 | 味の素株式会社 | 洗浄剤組成物 |
| US5277811A (en) * | 1992-04-14 | 1994-01-11 | Millipore Corporation | Process for forming porous polymeric product from a nonporous polymeric composition and product |
| JPH115753A (ja) * | 1997-06-17 | 1999-01-12 | Nippon Kayaku Co Ltd | 光学分割剤及びそれを用いる光学分割法 |
| BE1012622A3 (fr) | 1999-04-21 | 2001-01-09 | Solvay | Procede pour la separation d'enantiomeres et reactif enantiopur. |
| DE60035603T2 (de) | 1999-09-17 | 2008-05-21 | Mip Technologies Ab | Neue molekular geprägte und auf einen festen träger gepfropfte polymere |
| US6485650B1 (en) | 2000-08-28 | 2002-11-26 | Facilichem, Inc. | Liquid membrane separation of enantiomers |
| JP2007253109A (ja) * | 2006-03-24 | 2007-10-04 | Nitto Denko Corp | 乾燥複合半透膜の製造方法 |
| JP2009091535A (ja) * | 2007-10-10 | 2009-04-30 | Plascoat Kk | 光学活性ポリマー |
-
2010
- 2010-03-25 CN CN201080022405.5A patent/CN102438734B/zh not_active Expired - Fee Related
- 2010-03-25 DE DE112010001374T patent/DE112010001374T5/de not_active Ceased
- 2010-03-25 WO PCT/IN2010/000188 patent/WO2010109490A1/en active Application Filing
- 2010-03-25 KR KR1020117025333A patent/KR101573968B1/ko not_active IP Right Cessation
- 2010-03-25 JP JP2012501507A patent/JP5619867B2/ja not_active Expired - Fee Related
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2233248A (en) * | 1989-06-07 | 1991-01-09 | Aligena Ag | Enantiomer enrichment by membrane processes |
| US6270640B1 (en) * | 1998-04-29 | 2001-08-07 | Board Of Supervisors Of Louisiana State University And Agricultural And Mechanical College | Polymerized oligopeptide-surfactant chiral micelles |
| CN1772356A (zh) * | 2005-11-02 | 2006-05-17 | 华东理工大学 | 一种手性分子印迹纤维复合膜及其制备方法和应用 |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2012521869A (ja) | 2012-09-20 |
| KR101573968B1 (ko) | 2015-12-02 |
| DE112010001374T5 (de) | 2012-07-26 |
| JP5619867B2 (ja) | 2014-11-05 |
| KR20120012801A (ko) | 2012-02-10 |
| WO2010109490A1 (en) | 2010-09-30 |
| CN102438734A (zh) | 2012-05-02 |
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