JPS6353855B2 - - Google Patents
Info
- Publication number
- JPS6353855B2 JPS6353855B2 JP59044065A JP4406584A JPS6353855B2 JP S6353855 B2 JPS6353855 B2 JP S6353855B2 JP 59044065 A JP59044065 A JP 59044065A JP 4406584 A JP4406584 A JP 4406584A JP S6353855 B2 JPS6353855 B2 JP S6353855B2
- Authority
- JP
- Japan
- Prior art keywords
- crosslinked polymer
- production example
- group
- adsorbent
- optically active
- 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
Links
- 229920006037 cross link polymer Polymers 0.000 claims description 87
- 239000002253 acid Substances 0.000 claims description 36
- 239000003463 adsorbent Substances 0.000 claims description 34
- 239000000470 constituent Substances 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000000962 organic group Chemical group 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 description 56
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 32
- 239000000243 solution Substances 0.000 description 31
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 30
- 238000000034 method Methods 0.000 description 30
- 239000000203 mixture Substances 0.000 description 30
- 125000003277 amino group Chemical group 0.000 description 27
- -1 poly(triphenylmethyl methacrylate) Polymers 0.000 description 25
- 229940024606 amino acid Drugs 0.000 description 24
- 235000001014 amino acid Nutrition 0.000 description 23
- 150000001413 amino acids Chemical class 0.000 description 22
- 229910052757 nitrogen Inorganic materials 0.000 description 19
- 238000006243 chemical reaction Methods 0.000 description 18
- 238000006116 polymerization reaction Methods 0.000 description 17
- 239000002904 solvent Substances 0.000 description 17
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
- 229920001577 copolymer Polymers 0.000 description 15
- 239000000178 monomer Substances 0.000 description 15
- 238000001179 sorption measurement Methods 0.000 description 14
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- 230000003287 optical effect Effects 0.000 description 12
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 11
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- 125000000524 functional group Chemical group 0.000 description 10
- 239000003960 organic solvent Substances 0.000 description 10
- 229920000835 poly(gamma-benzyl-L-glutamate) polymer Polymers 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000003999 initiator Substances 0.000 description 9
- 229920001308 poly(aminoacid) Polymers 0.000 description 9
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 9
- 238000000921 elemental analysis Methods 0.000 description 8
- 229910052739 hydrogen Inorganic materials 0.000 description 8
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
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- UQDJGEHQDNVPGU-UHFFFAOYSA-N serine phosphoethanolamine Chemical compound [NH3+]CCOP([O-])(=O)OCC([NH3+])C([O-])=O UQDJGEHQDNVPGU-UHFFFAOYSA-N 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 6
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 6
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- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 6
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 description 5
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- 229910001431 copper ion Inorganic materials 0.000 description 5
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- 239000003085 diluting agent Substances 0.000 description 5
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 5
- 229920002451 polyvinyl alcohol Polymers 0.000 description 5
- 238000010557 suspension polymerization reaction Methods 0.000 description 5
- IWTYTFSSTWXZFU-UHFFFAOYSA-N 3-chloroprop-1-enylbenzene Chemical compound ClCC=CC1=CC=CC=C1 IWTYTFSSTWXZFU-UHFFFAOYSA-N 0.000 description 4
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 4
- VGALFAWDSNRXJK-VIFPVBQESA-N L-aspartic acid beta-benzyl ester Chemical compound OC(=O)[C@@H](N)CC(=O)OCC1=CC=CC=C1 VGALFAWDSNRXJK-VIFPVBQESA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 150000001408 amides Chemical group 0.000 description 4
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 4
- 238000004587 chromatography analysis Methods 0.000 description 4
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 4
- IWYDHOAUDWTVEP-UHFFFAOYSA-N mandelic acid Chemical compound OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
- 102000004190 Enzymes Human genes 0.000 description 3
- 108090000790 Enzymes Proteins 0.000 description 3
- ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical compound CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 description 3
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 description 3
- KZSNJWFQEVHDMF-BYPYZUCNSA-N L-valine Chemical compound CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 description 3
- ROHFNLRQFUQHCH-UHFFFAOYSA-N Leucine Natural products CC(C)CC(N)C(O)=O ROHFNLRQFUQHCH-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- KZSNJWFQEVHDMF-UHFFFAOYSA-N Valine Natural products CC(C)C(N)C(O)=O KZSNJWFQEVHDMF-UHFFFAOYSA-N 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 239000000084 colloidal system Substances 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 239000003480 eluent Substances 0.000 description 3
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 230000002209 hydrophobic effect Effects 0.000 description 3
- 238000002329 infrared spectrum Methods 0.000 description 3
- 238000011068 loading method Methods 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 description 3
- 230000001681 protective effect Effects 0.000 description 3
- 235000018102 proteins Nutrition 0.000 description 3
- 102000004169 proteins and genes Human genes 0.000 description 3
- 108090000623 proteins and genes Proteins 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 239000004474 valine Substances 0.000 description 3
- VSJVTIUBGGZOSC-VUWPPUDQSA-N (2s)-2,5-diamino-6-oxo-6-phenylmethoxyhexanoic acid Chemical compound OC(=O)[C@@H](N)CCC(N)C(=O)OCC1=CC=CC=C1 VSJVTIUBGGZOSC-VUWPPUDQSA-N 0.000 description 2
- ATCFYQUZTYQTJN-AXDSSHIGSA-N (2s)-2-amino-4-benzylpentanedioic acid Chemical compound OC(=O)[C@@H](N)CC(C(O)=O)CC1=CC=CC=C1 ATCFYQUZTYQTJN-AXDSSHIGSA-N 0.000 description 2
- BGGHCRNCRWQABU-JTQLQIEISA-N (2s)-2-amino-5-oxo-5-phenylmethoxypentanoic acid Chemical compound OC(=O)[C@@H](N)CCC(=O)OCC1=CC=CC=C1 BGGHCRNCRWQABU-JTQLQIEISA-N 0.000 description 2
- QBFQXAKABOKEHT-JTQLQIEISA-N (2s)-3-(4-acetyloxyphenyl)-2-azaniumylpropanoate Chemical compound CC(=O)OC1=CC=C(C[C@H](N)C(O)=O)C=C1 QBFQXAKABOKEHT-JTQLQIEISA-N 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
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- DBCAQXHNJOFNGC-UHFFFAOYSA-N 4-bromo-1,1,1-trifluorobutane Chemical compound FC(F)(F)CCCBr DBCAQXHNJOFNGC-UHFFFAOYSA-N 0.000 description 2
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- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 2
- 101100189558 Arabidopsis thaliana BOA gene Proteins 0.000 description 2
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
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- 238000012360 testing method Methods 0.000 description 2
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- RQEUFEKYXDPUSK-ZETCQYMHSA-N (1S)-1-phenylethanamine Chemical compound C[C@H](N)C1=CC=CC=C1 RQEUFEKYXDPUSK-ZETCQYMHSA-N 0.000 description 1
- QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 description 1
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Landscapes
- Peptides Or Proteins (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
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Claims (1)
- ãç¹èš±è«æ±ã®ç¯å²ã ïŒ äžè¬åŒã ïŒåŒäžãïœã¯ïŒä»¥äžã®æŽæ°ã§ãããã¯ææ©åºã
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Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4406584A JPS60193538A (ja) | 1984-03-09 | 1984-03-09 | åžçå€ |
| US06/708,935 US4694044A (en) | 1984-03-09 | 1985-03-06 | Adsorbent |
| EP19850102587 EP0154343B1 (en) | 1984-03-09 | 1985-03-07 | Adsorbent |
| DE8585102587T DE3583248D1 (de) | 1984-03-09 | 1985-03-07 | Adsorbentmittel. |
| US07/026,970 US4747956A (en) | 1984-03-09 | 1987-03-17 | Method of adsorbing subtances |
| US07/152,444 US4785021A (en) | 1984-03-09 | 1988-02-05 | Adsorbent and method of preparation |
| JP18529990A JPH03267148A (ja) | 1984-03-09 | 1990-07-16 | å åŠæŽ»æ§ç©è³ªã®åå²çšåžçå€ |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4406584A JPS60193538A (ja) | 1984-03-09 | 1984-03-09 | åžçå€ |
Related Child Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2185300A Division JPH06197B2 (ja) | 1990-07-16 | 1990-07-16 | åžçå€ |
| JP18529990A Division JPH03267148A (ja) | 1984-03-09 | 1990-07-16 | å åŠæŽ»æ§ç©è³ªã®åå²çšåžçå€ |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS60193538A JPS60193538A (ja) | 1985-10-02 |
| JPS6353855B2 true JPS6353855B2 (ja) | 1988-10-25 |
Family
ID=12681221
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP4406584A Granted JPS60193538A (ja) | 1984-03-09 | 1984-03-09 | åžçå€ |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS60193538A (ja) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS60193929A (ja) * | 1984-03-13 | 1985-10-02 | Daicel Chem Ind Ltd | åé¢å€ |
| JPH0651797B2 (ja) * | 1985-11-20 | 1994-07-06 | å¿ äž å¹³å±± | ããªã¢ããé žã®æ¶æ©çç¶ç²åãšãã®è£œé æ¹æ³ |
| JP6154807B2 (ja) | 2012-05-23 | 2017-06-28 | æ ªåŒäŒç€Ÿãã€ã»ã« | åé¢å€ |
| CN109569532B (zh) | 2012-12-06 | 2021-12-14 | æ ªåŒäŒç€Ÿå€§èµç | å犻å |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS529233A (en) * | 1975-07-08 | 1977-01-24 | Connell James | Wheel cover assembly |
| JPS529479A (en) * | 1975-07-07 | 1977-01-25 | Haaku Inc | Torque measuring device for gear train |
| JPS529478A (en) * | 1975-07-05 | 1977-01-25 | Danfoss As | Circuit system for detecting physical ouantity such as flow rate of flowing medium by supersonic method |
-
1984
- 1984-03-09 JP JP4406584A patent/JPS60193538A/ja active Granted
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS529478A (en) * | 1975-07-05 | 1977-01-25 | Danfoss As | Circuit system for detecting physical ouantity such as flow rate of flowing medium by supersonic method |
| JPS529479A (en) * | 1975-07-07 | 1977-01-25 | Haaku Inc | Torque measuring device for gear train |
| JPS529233A (en) * | 1975-07-08 | 1977-01-24 | Connell James | Wheel cover assembly |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS60193538A (ja) | 1985-10-02 |
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