JP2005510593A5 - - Google Patents
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- JP2005510593A5 JP2005510593A5 JP2003547474A JP2003547474A JP2005510593A5 JP 2005510593 A5 JP2005510593 A5 JP 2005510593A5 JP 2003547474 A JP2003547474 A JP 2003547474A JP 2003547474 A JP2003547474 A JP 2003547474A JP 2005510593 A5 JP2005510593 A5 JP 2005510593A5
- Authority
- JP
- Japan
- Prior art keywords
- support
- post
- porous polymeric
- grafting
- polymeric polysaccharide
- 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
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- 150000001875 compounds Chemical class 0.000 claims description 60
- 150000004676 glycans Polymers 0.000 claims description 39
- 229920001282 polysaccharide Polymers 0.000 claims description 39
- 239000005017 polysaccharide Substances 0.000 claims description 39
- 150000004804 polysaccharides Polymers 0.000 claims description 39
- 229920000642 polymer Polymers 0.000 claims description 26
- 238000004587 chromatography analysis Methods 0.000 claims description 15
- 238000000926 separation method Methods 0.000 claims description 14
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 13
- 239000002245 particle Substances 0.000 claims description 11
- -1 hydroxyalkyl vinyl ether Chemical compound 0.000 claims description 10
- 239000003999 initiator Substances 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 230000027455 binding Effects 0.000 claims description 7
- 125000000524 functional group Chemical group 0.000 claims description 7
- 239000003446 ligand Substances 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
- 238000002715 modification method Methods 0.000 claims description 6
- MYMOFIZGZYHOMD-UHFFFAOYSA-N oxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 6
- 239000001301 oxygen Substances 0.000 claims description 6
- HMBNQNDUEFFFNZ-UHFFFAOYSA-N 4-ethenoxybutan-1-ol Chemical compound OCCCCOC=C HMBNQNDUEFFFNZ-UHFFFAOYSA-N 0.000 claims description 5
- 150000002118 epoxides Chemical class 0.000 claims description 5
- 238000005406 washing Methods 0.000 claims description 5
- 238000007348 radical reaction Methods 0.000 claims description 3
- 125000005670 ethenylalkyl group Chemical group 0.000 claims description 2
- 239000007791 liquid phase Substances 0.000 claims description 2
- 238000006011 modification reaction Methods 0.000 description 28
- QYKIQEUNHZKYBP-UHFFFAOYSA-N vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 24
- 229920002684 Sepharose Polymers 0.000 description 22
- 238000004191 hydrophobic interaction chromatography Methods 0.000 description 17
- 238000006116 polymerization reaction Methods 0.000 description 14
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 13
- 229920000936 Agarose Polymers 0.000 description 13
- UZKWTJUDCOPSNM-UHFFFAOYSA-N 1-ethenoxybutane Chemical compound CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 11
- 230000002209 hydrophobic Effects 0.000 description 11
- 239000000178 monomer Substances 0.000 description 11
- 235000018102 proteins Nutrition 0.000 description 10
- 108090000623 proteins and genes Proteins 0.000 description 10
- 102000004169 proteins and genes Human genes 0.000 description 10
- 239000000126 substance Substances 0.000 description 10
- 239000011159 matrix material Substances 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- 238000004366 reverse phase liquid chromatography Methods 0.000 description 9
- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 description 8
- 239000011148 porous material Substances 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 230000004048 modification Effects 0.000 description 6
- 238000010526 radical polymerization reaction Methods 0.000 description 6
- 229920002307 Dextran Polymers 0.000 description 5
- 239000011248 coating agent Substances 0.000 description 5
- 230000000875 corresponding Effects 0.000 description 5
- 239000000499 gel Substances 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 4
- 102000004877 Insulin Human genes 0.000 description 4
- 108090001061 Insulin Proteins 0.000 description 4
- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- 239000000377 silicon dioxide Substances 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 238000007792 addition Methods 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 150000001768 cations Chemical class 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 150000003983 crown ethers Chemical group 0.000 description 3
- 238000001212 derivatisation Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 125000001165 hydrophobic group Chemical group 0.000 description 3
- 230000003993 interaction Effects 0.000 description 3
- 238000004255 ion exchange chromatography Methods 0.000 description 3
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000003440 styrenes Chemical class 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- COXCGWKSEPPDAA-UHFFFAOYSA-N 2,4-dimethylpentanenitrile Chemical compound CC(C)CC(C)C#N COXCGWKSEPPDAA-UHFFFAOYSA-N 0.000 description 2
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- LSWYGACWGAICNM-UHFFFAOYSA-N 2-(prop-2-enoxymethyl)oxirane Chemical group C=CCOCC1CO1 LSWYGACWGAICNM-UHFFFAOYSA-N 0.000 description 2
- OZAIFHULBGXAKX-VAWYXSNFSA-N Azobisisobutyronitrile Chemical compound N#CC(C)(C)\N=N\C(C)(C)C#N OZAIFHULBGXAKX-VAWYXSNFSA-N 0.000 description 2
- 102100016653 LALBA Human genes 0.000 description 2
- 101700017573 LALBA Proteins 0.000 description 2
- FPYJFEHAWHCUMM-UHFFFAOYSA-N Maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 2
- 102000036913 Myoglobin Human genes 0.000 description 2
- 108010062374 Myoglobin Proteins 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 238000005937 allylation reaction Methods 0.000 description 2
- 239000011324 bead Substances 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N butadiene Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 239000012504 chromatography matrix Substances 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- KZMGYPLQYOPHEL-UHFFFAOYSA-N ethoxyethane;trifluoroborane Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- CTKINSOISVBQLD-UHFFFAOYSA-N glycidol Chemical compound OCC1CO1 CTKINSOISVBQLD-UHFFFAOYSA-N 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- 125000003010 ionic group Chemical group 0.000 description 2
- 125000005647 linker group Chemical group 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 229920001059 synthetic polymer Polymers 0.000 description 2
- 229920000208 temperature-responsive polymer Polymers 0.000 description 2
- 235000021241 α-lactalbumin Nutrition 0.000 description 2
- OZCMOJQQLBXBKI-UHFFFAOYSA-N 1-ethenoxy-2-methylpropane Chemical compound CC(C)COC=C OZCMOJQQLBXBKI-UHFFFAOYSA-N 0.000 description 1
- QJJDJWUCRAPCOL-UHFFFAOYSA-N 1-ethenoxyoctadecane Chemical compound CCCCCCCCCCCCCCCCCCOC=C QJJDJWUCRAPCOL-UHFFFAOYSA-N 0.000 description 1
- WYGWHHGCAGTUCH-UHFFFAOYSA-N 2-[(2-cyano-4-methylpentan-2-yl)diazenyl]-2,4-dimethylpentanenitrile Chemical compound CC(C)CC(C)(C#N)N=NC(C)(C#N)CC(C)C WYGWHHGCAGTUCH-UHFFFAOYSA-N 0.000 description 1
- PGYJSURPYAAOMM-UHFFFAOYSA-N 2-ethenoxy-2-methylpropane Chemical compound CC(C)(C)OC=C PGYJSURPYAAOMM-UHFFFAOYSA-N 0.000 description 1
- VUIWJRYTWUGOOF-UHFFFAOYSA-N 2-ethenoxyethanol Chemical compound OCCOC=C VUIWJRYTWUGOOF-UHFFFAOYSA-N 0.000 description 1
- JJRDRFZYKKFYMO-UHFFFAOYSA-N 2-methyl-2-(2-methylbutan-2-ylperoxy)butane Chemical compound CCC(C)(C)OOC(C)(C)CC JJRDRFZYKKFYMO-UHFFFAOYSA-N 0.000 description 1
- MXRGSJAOLKBZLU-UHFFFAOYSA-N 3-ethenylazepan-2-one Chemical compound C=CC1CCCCNC1=O MXRGSJAOLKBZLU-UHFFFAOYSA-N 0.000 description 1
- QZPSOSOOLFHYRR-UHFFFAOYSA-N 3-hydroxypropyl prop-2-enoate Chemical compound OCCCOC(=O)C=C QZPSOSOOLFHYRR-UHFFFAOYSA-N 0.000 description 1
- KYIKRXIYLAGAKQ-UHFFFAOYSA-N ABCN Chemical compound C1CCCCC1(C#N)N=NC1(C#N)CCCCC1 KYIKRXIYLAGAKQ-UHFFFAOYSA-N 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- BHELZAPQIKSEDF-UHFFFAOYSA-N Allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 1
- OSDWBNJEKMUWAV-UHFFFAOYSA-N Allyl chloride Chemical compound ClCC=C OSDWBNJEKMUWAV-UHFFFAOYSA-N 0.000 description 1
- 241001312219 Amorphophallus konjac Species 0.000 description 1
- 235000001206 Amorphophallus rivieri Nutrition 0.000 description 1
- 229940113118 Carrageenan Drugs 0.000 description 1
- 229920001661 Chitosan Polymers 0.000 description 1
- 239000004971 Cross linker Substances 0.000 description 1
- ZQMIGQNCOMNODD-UHFFFAOYSA-N Diacetyl peroxide Chemical compound CC(=O)OOC(C)=O ZQMIGQNCOMNODD-UHFFFAOYSA-N 0.000 description 1
- 229920002148 Gellan gum Polymers 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Incidol Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- 229920002752 Konjac Polymers 0.000 description 1
- YIVJZNGAASQVEM-UHFFFAOYSA-N Lauroyl peroxide Chemical compound CCCCCCCCCCCC(=O)OOC(=O)CCCCCCCCCCC YIVJZNGAASQVEM-UHFFFAOYSA-N 0.000 description 1
- FQPSGWSUVKBHSU-UHFFFAOYSA-N Methacrylamide Chemical group CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 1
- XJRBAMWJDBPFIM-UHFFFAOYSA-N Methyl vinyl ether Chemical compound COC=C XJRBAMWJDBPFIM-UHFFFAOYSA-N 0.000 description 1
- ZIUHHBKFKCYYJD-UHFFFAOYSA-N N,N'-Methylenebisacrylamide Chemical compound C=CC(=O)NCNC(=O)C=C ZIUHHBKFKCYYJD-UHFFFAOYSA-N 0.000 description 1
- 102000005891 Pancreatic ribonucleases Human genes 0.000 description 1
- 108020002230 Pancreatic ribonucleases Proteins 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 102000006382 Ribonucleases Human genes 0.000 description 1
- 108010083644 Ribonucleases Proteins 0.000 description 1
- OKKRPWIIYQTPQF-UHFFFAOYSA-N Trimethylolpropane trimethacrylate Chemical compound CC(=C)C(=O)OCC(CC)(COC(=O)C(C)=C)COC(=O)C(C)=C OKKRPWIIYQTPQF-UHFFFAOYSA-N 0.000 description 1
- WYGWHHGCAGTUCH-ISLYRVAYSA-N V-65 Substances CC(C)CC(C)(C#N)\N=N\C(C)(C#N)CC(C)C WYGWHHGCAGTUCH-ISLYRVAYSA-N 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- 150000003926 acrylamides Chemical group 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 238000001042 affinity chromatography Methods 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 229940072056 alginate Drugs 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 108010027597 alpha-chymotrypsin Proteins 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 230000001588 bifunctional Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 125000004432 carbon atoms Chemical group C* 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 125000003262 carboxylic acid ester group Chemical group [H]C([H])([*:2])OC(=O)C([H])([H])[*:1] 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 239000000679 carrageenan Substances 0.000 description 1
- 235000010418 carrageenan Nutrition 0.000 description 1
- 229920001525 carrageenan Polymers 0.000 description 1
- 238000005341 cation exchange Methods 0.000 description 1
- 239000003729 cation exchange resin Substances 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 238000010538 cationic polymerization reaction Methods 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 238000003889 chemical engineering Methods 0.000 description 1
- 239000012539 chromatography resin Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000011557 critical solution Substances 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 101700065061 ctrA Proteins 0.000 description 1
- AVQDUZVGWWQPHP-UHFFFAOYSA-N cyclohexane;ethenoxyethene;methanol Chemical compound OC.OC.C=COC=C.C1CCCCC1 AVQDUZVGWWQPHP-UHFFFAOYSA-N 0.000 description 1
- 230000001419 dependent Effects 0.000 description 1
- 238000010511 deprotection reaction Methods 0.000 description 1
- 238000010894 electron beam technology Methods 0.000 description 1
- GKIPXFAANLTWBM-UHFFFAOYSA-N epibromohydrin Chemical compound BrCC1CO1 GKIPXFAANLTWBM-UHFFFAOYSA-N 0.000 description 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- VGIYPVFBQRUBDD-UHFFFAOYSA-N ethenoxycyclohexane Chemical compound C=COC1CCCCC1 VGIYPVFBQRUBDD-UHFFFAOYSA-N 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000001595 flow curve Methods 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 238000005755 formation reaction Methods 0.000 description 1
- 229920001002 functional polymer Polymers 0.000 description 1
- 238000001879 gelation Methods 0.000 description 1
- 229920000578 graft polymer Polymers 0.000 description 1
- 150000004820 halides Chemical group 0.000 description 1
- 125000005842 heteroatoms Chemical group 0.000 description 1
- 230000005660 hydrophilic surface Effects 0.000 description 1
- 229920001600 hydrophobic polymer Polymers 0.000 description 1
- 230000005661 hydrophobic surface Effects 0.000 description 1
- 230000000977 initiatory Effects 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000000252 konjac Substances 0.000 description 1
- 235000010485 konjac Nutrition 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atoms Chemical group N* 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N oxane Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 125000001918 phosphonic acid ester group Chemical group 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000002952 polymeric resin Substances 0.000 description 1
- 239000002685 polymerization catalyst Substances 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 238000004237 preparative chromatography Methods 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000007717 redox polymerization reaction Methods 0.000 description 1
- 230000002441 reversible Effects 0.000 description 1
- 125000002130 sulfonic acid ester group Chemical group 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000010557 suspension polymerization reaction Methods 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 230000004584 weight gain Effects 0.000 description 1
- 235000019786 weight gain Nutrition 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE0103968 | 2001-11-26 | ||
| SE0103968-4 | 2001-11-26 | ||
| SE0202075-8 | 2002-06-28 | ||
| SE0202075A SE0202075D0 (sv) | 2002-06-28 | 2002-06-28 | Post-modification of a porous support |
| PCT/SE2002/002173 WO2003046027A1 (en) | 2001-11-26 | 2002-11-26 | Post-modification of a porous support |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2005510593A JP2005510593A (ja) | 2005-04-21 |
| JP2005510593A5 true JP2005510593A5 (US06265458-20010724-C00056.png) | 2009-04-16 |
| JP5280604B2 JP5280604B2 (ja) | 2013-09-04 |
Family
ID=26655605
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003547474A Expired - Fee Related JP5280604B2 (ja) | 2001-11-26 | 2002-11-26 | 多孔性支持体の後修飾 |
Country Status (7)
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8147562B2 (en) * | 2002-09-23 | 2012-04-03 | The General Hospital Corporation | Three dimensional construct for the design and fabrication of physiological fluidic networks |
| SE0302509D0 (sv) | 2003-09-19 | 2003-09-19 | Amersham Biosciences Ab | Matrix for separation of polyethers and method of separation |
| WO2005078028A1 (en) * | 2004-02-05 | 2005-08-25 | Millipore Corporation | Method of forming polysaccharide structures |
| US7687619B2 (en) * | 2004-02-05 | 2010-03-30 | Millipore Corporation | Room temperature stable agarose solutions |
| FR2884253B1 (fr) * | 2005-04-08 | 2007-06-22 | Univ Lille Sciences Tech | Materiaux monolithiques fonctionnalisables |
| EP1967644A1 (en) * | 2007-03-07 | 2008-09-10 | Jacobs University Bremen gGmbH | Composite microfibre |
| EP2285485B1 (de) * | 2008-05-30 | 2014-04-23 | Merck Patent GmbH | Ce(iv) initiierte pfropfpolymerisation auf nicht hydroxylgruppenhaltigen polymeren |
| WO2010126087A1 (ja) * | 2009-04-30 | 2010-11-04 | ダイセル化学工業株式会社 | 光学異性体用分離剤 |
| JP5672892B2 (ja) * | 2009-09-18 | 2015-02-18 | 学校法人東京理科大学 | リガンド固定化用共重合体及び該共重合体によるリガンドの固定化方法 |
| JP5474881B2 (ja) * | 2010-07-28 | 2014-04-16 | ローム アンド ハース カンパニー | 向上したクロマトグラフィー媒体の製造方法および使用方法 |
| SG185590A1 (en) * | 2010-07-29 | 2012-12-28 | Emd Millipore Corp | Grafting method to improve chromatography media performance |
| WO2014069474A1 (ja) | 2012-10-30 | 2014-05-08 | 株式会社クラレ | 多孔質グラフト共重合体粒子、その製造方法及びそれを用いた吸着材 |
| JP6576335B2 (ja) | 2013-10-03 | 2019-09-18 | スリーエム イノベイティブ プロパティズ カンパニー | 結合能力が向上したリガンド官能化基材 |
| US20160243526A1 (en) * | 2013-10-10 | 2016-08-25 | Ge Healthcare Bio-Sciences Ab | Method for production of a chromatography material |
| JP6733166B2 (ja) * | 2015-12-11 | 2020-07-29 | 日立化成株式会社 | 分離材用の多孔質ポリマ粒子の製造方法、分離材用の多孔質ポリマ粒子、及びカラム |
| JP6913901B2 (ja) * | 2017-01-12 | 2021-08-04 | 国立大学法人福井大学 | コア−シェル型高分子微粒子、粒子分散液及び前記微粒子の製造方法 |
| JP6939021B2 (ja) * | 2017-03-30 | 2021-09-22 | 昭和電工マテリアルズ株式会社 | 分離材及びカラム |
| CN115044068A (zh) * | 2022-03-24 | 2022-09-13 | 苏州星谱生物科技有限公司 | 一种高强度琼脂糖微球的制备方法 |
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| JPS5243499B2 (US06265458-20010724-C00056.png) * | 1973-08-31 | 1977-10-31 | ||
| SE420838B (sv) * | 1975-12-12 | 1981-11-02 | Pharmacia Fine Chemicals Ab | Dextranderivatgel i partikelform for separationsendamal |
| SE417431B (sv) * | 1975-12-12 | 1981-03-16 | Pharmacia Fine Chemicals Ab | Dextranderivatgel for elektroforetisk separation |
| US4079025A (en) * | 1976-04-27 | 1978-03-14 | A. E. Staley Manufacturing Company | Copolymerized starch composition |
| JPS55123610A (en) * | 1979-03-17 | 1980-09-24 | Nichiden Kagaku Kk | Modified starch and its preparation |
| US4540742A (en) * | 1982-11-12 | 1985-09-10 | The B. F. Goodrich Company | Graft copolymers and process for their preparation |
| JPS6058415A (ja) * | 1983-09-10 | 1985-04-04 | Nippon Paint Co Ltd | グラフト共重合体樹脂の製造法 |
| DE3811042A1 (de) * | 1988-03-31 | 1989-10-19 | Merck Patent Gmbh | Ionenaustauscher |
| US6022902A (en) | 1989-10-31 | 2000-02-08 | The United States Of America As Represented By The Administrator Of The National Aeronautics And Space Administration | Porous article with surface functionality and method for preparing same |
| JPH05170845A (ja) * | 1991-12-20 | 1993-07-09 | Nippon Paint Co Ltd | 有機ポリマー微粒子およびその製法 |
| JPH08502534A (ja) * | 1992-10-21 | 1996-03-19 | コーネル リサーチ ファウンデーション、インコーポレーテッド | 多孔物質の細孔サイズ選択的修飾法 |
| SE9303790D0 (sv) * | 1993-11-17 | 1993-11-17 | Pharmacia Lkb Biotech | A method for separation and synthetic polymers that can be used as separation media in the method |
| JP3446274B2 (ja) * | 1993-12-21 | 2003-09-16 | 三菱化学株式会社 | 分離剤の製造方法 |
| TW307775B (en) * | 1994-02-15 | 1997-06-11 | Novartis Erfind Verwalt Gmbh | Unsaturated carbohydrate derivatives, polymers thereof and their use |
| US5503933A (en) * | 1994-02-25 | 1996-04-02 | Purdue Research Foundation | Covalently bonded coatings |
| US5929214A (en) | 1997-02-28 | 1999-07-27 | Cornell Research Foundation, Inc. | Thermally responsive polymer monoliths |
| US5865994A (en) | 1997-03-13 | 1999-02-02 | Dionex Corporation | Bifunctional crown ether-based cation-exchange stationary phase for liquid chromatography |
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| TW594416B (en) * | 2001-05-08 | 2004-06-21 | Shipley Co Llc | Photoimageable composition |
| EP1448684A1 (en) * | 2001-11-26 | 2004-08-25 | Amersham Biosciences AB | Post-modification of a porous support |
-
2002
- 2002-11-26 JP JP2003547474A patent/JP5280604B2/ja not_active Expired - Fee Related
- 2002-11-26 AU AU2002353736A patent/AU2002353736B2/en not_active Ceased
- 2002-11-26 AT AT02789112T patent/ATE512175T1/de not_active IP Right Cessation
- 2002-11-26 WO PCT/SE2002/002173 patent/WO2003046027A1/en active Application Filing
- 2002-11-26 US US10/496,762 patent/US7048858B2/en not_active Expired - Lifetime
- 2002-11-26 EP EP02789112A patent/EP1448638B8/en not_active Expired - Lifetime
- 2002-11-26 CA CA002464302A patent/CA2464302A1/en not_active Abandoned
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