JP4988574B2 - マクロ孔質イオン交換樹脂 - Google Patents
マクロ孔質イオン交換樹脂 Download PDFInfo
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- JP4988574B2 JP4988574B2 JP2007527250A JP2007527250A JP4988574B2 JP 4988574 B2 JP4988574 B2 JP 4988574B2 JP 2007527250 A JP2007527250 A JP 2007527250A JP 2007527250 A JP2007527250 A JP 2007527250A JP 4988574 B2 JP4988574 B2 JP 4988574B2
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- Prior art keywords
- ion exchange
- exchange resin
- monomer
- monomers
- meth
- 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
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- 239000003456 ion exchange resin Substances 0.000 title claims description 173
- 229920003303 ion-exchange polymer Polymers 0.000 title claims description 173
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 title claims description 158
- 239000000178 monomer Substances 0.000 claims description 265
- 239000000203 mixture Substances 0.000 claims description 110
- 229910052757 nitrogen Inorganic materials 0.000 claims description 86
- 239000002245 particle Substances 0.000 claims description 51
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 38
- 238000004132 cross linking Methods 0.000 claims description 34
- 150000003839 salts Chemical class 0.000 claims description 20
- 239000007795 chemical reaction product Substances 0.000 claims description 16
- 239000002131 composite material Substances 0.000 claims description 15
- 239000011159 matrix material Substances 0.000 claims description 15
- 238000001914 filtration Methods 0.000 claims description 8
- 125000003277 amino group Chemical group 0.000 claims description 3
- KMBSSXSNDSJXCG-UHFFFAOYSA-N 1-[2-(2-hydroxyundecylamino)ethylamino]undecan-2-ol Chemical compound CCCCCCCCCC(O)CNCCNCC(O)CCCCCCCCC KMBSSXSNDSJXCG-UHFFFAOYSA-N 0.000 claims 1
- 125000000542 sulfonic acid group Chemical group 0.000 claims 1
- 238000000034 method Methods 0.000 description 48
- 239000002801 charged material Substances 0.000 description 25
- 239000000463 material Substances 0.000 description 25
- 239000008346 aqueous phase Substances 0.000 description 24
- 238000004587 chromatography analysis Methods 0.000 description 22
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 18
- 239000003729 cation exchange resin Substances 0.000 description 16
- -1 acryl Chemical group 0.000 description 15
- 239000003957 anion exchange resin Substances 0.000 description 15
- 229920001577 copolymer Polymers 0.000 description 14
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- 238000006116 polymerization reaction Methods 0.000 description 13
- 102000016943 Muramidase Human genes 0.000 description 12
- 108010014251 Muramidase Proteins 0.000 description 12
- 108010062010 N-Acetylmuramoyl-L-alanine Amidase Proteins 0.000 description 12
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- 102000004169 proteins and genes Human genes 0.000 description 11
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- 239000000872 buffer Substances 0.000 description 10
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 9
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- 238000000746 purification Methods 0.000 description 9
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 8
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
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- 108091003079 Bovine Serum Albumin Proteins 0.000 description 7
- 150000003254 radicals Chemical class 0.000 description 7
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
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- 239000012071 phase Substances 0.000 description 6
- 239000011347 resin Substances 0.000 description 6
- 229920005989 resin Polymers 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 239000007993 MOPS buffer Substances 0.000 description 5
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- 239000007864 aqueous solution Substances 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 238000005341 cation exchange Methods 0.000 description 5
- 229940023913 cation exchange resins Drugs 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 5
- 239000004810 polytetrafluoroethylene Substances 0.000 description 5
- 238000000926 separation method Methods 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- LCPVQAHEFVXVKT-UHFFFAOYSA-N 2-(2,4-difluorophenoxy)pyridin-3-amine Chemical compound NC1=CC=CN=C1OC1=CC=C(F)C=C1F LCPVQAHEFVXVKT-UHFFFAOYSA-N 0.000 description 4
- 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 4
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 4
- DVLFYONBTKHTER-UHFFFAOYSA-N 3-(N-morpholino)propanesulfonic acid Chemical compound OS(=O)(=O)CCCN1CCOCC1 DVLFYONBTKHTER-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 125000003010 ionic group Chemical group 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- CHQMHPLRPQMAMX-UHFFFAOYSA-L sodium persulfate Substances [Na+].[Na+].[O-]S(=O)(=O)OOS([O-])(=O)=O CHQMHPLRPQMAMX-UHFFFAOYSA-L 0.000 description 4
- 238000010557 suspension polymerization reaction Methods 0.000 description 4
- IRLPACMLTUPBCL-KQYNXXCUSA-N 5'-adenylyl sulfate Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](COP(O)(=O)OS(O)(=O)=O)[C@@H](O)[C@H]1O IRLPACMLTUPBCL-KQYNXXCUSA-N 0.000 description 3
- DXPPIEDUBFUSEZ-UHFFFAOYSA-N 6-methylheptyl prop-2-enoate Chemical compound CC(C)CCCCCOC(=O)C=C DXPPIEDUBFUSEZ-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium peroxydisulfate Substances [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 3
- VAZSKTXWXKYQJF-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)OOS([O-])=O VAZSKTXWXKYQJF-UHFFFAOYSA-N 0.000 description 3
- 229910001870 ammonium persulfate Inorganic materials 0.000 description 3
- 239000000337 buffer salt Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000006184 cosolvent Substances 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 229920001519 homopolymer Polymers 0.000 description 3
- 230000003993 interaction Effects 0.000 description 3
- JRKICGRDRMAZLK-UHFFFAOYSA-L persulfate group Chemical group S(=O)(=O)([O-])OOS(=O)(=O)[O-] JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 3
- 230000000379 polymerizing effect Effects 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000003381 stabilizer Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- WZCPGDMVLDDOOX-UHFFFAOYSA-N 2-methyl-2-(prop-2-enoylamino)propanamide Chemical compound NC(=O)C(C)(C)NC(=O)C=C WZCPGDMVLDDOOX-UHFFFAOYSA-N 0.000 description 2
- FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 229920000936 Agarose Polymers 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 108010041986 DNA Vaccines Proteins 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 102000004190 Enzymes Human genes 0.000 description 2
- 108090000790 Enzymes Proteins 0.000 description 2
- OWXMKDGYPWMGEB-UHFFFAOYSA-N HEPPS Chemical compound OCCN1CCN(CCCS(O)(=O)=O)CC1 OWXMKDGYPWMGEB-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000004147 Sorbitan trioleate Substances 0.000 description 2
- PRXRUNOAOLTIEF-ADSICKODSA-N Sorbitan trioleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@@H](OC(=O)CCCCCCC\C=C/CCCCCCCC)[C@H]1OC[C@H](O)[C@H]1OC(=O)CCCCCCC\C=C/CCCCCCCC PRXRUNOAOLTIEF-ADSICKODSA-N 0.000 description 2
- 230000002776 aggregation Effects 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- 239000011324 bead Substances 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
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- 238000003795 desorption Methods 0.000 description 2
- ZQMIGQNCOMNODD-UHFFFAOYSA-N diacetyl peroxide Chemical compound CC(=O)OOC(C)=O ZQMIGQNCOMNODD-UHFFFAOYSA-N 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 229940088598 enzyme Drugs 0.000 description 2
- IMBKASBLAKCLEM-UHFFFAOYSA-L ferrous ammonium sulfate (anhydrous) Chemical compound [NH4+].[NH4+].[Fe+2].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O IMBKASBLAKCLEM-UHFFFAOYSA-L 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 2
- 239000008240 homogeneous mixture Substances 0.000 description 2
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 150000002432 hydroperoxides Chemical class 0.000 description 2
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- 108700021021 mRNA Vaccine Proteins 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
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- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
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- 238000010998 test method Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
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- SQTUYFKNCCBFRR-UHFFFAOYSA-N (2,4-dimethoxyphenyl)boronic acid Chemical compound COC1=CC=C(B(O)O)C(OC)=C1 SQTUYFKNCCBFRR-UHFFFAOYSA-N 0.000 description 1
- NIBPGNKODUOZIW-UHFFFAOYSA-M (2-hydroxy-3-prop-2-enoyloxypropyl)-trimethylazanium;chloride Chemical compound [Cl-].C[N+](C)(C)CC(O)COC(=O)C=C NIBPGNKODUOZIW-UHFFFAOYSA-M 0.000 description 1
- UILJLCFPJOIGLP-BYPYZUCNSA-N (2s)-2-(prop-2-enoylamino)butanedioic acid Chemical compound OC(=O)C[C@@H](C(O)=O)NC(=O)C=C UILJLCFPJOIGLP-BYPYZUCNSA-N 0.000 description 1
- KKSNTCYLMGYFFB-UHFFFAOYSA-N (prop-2-enoylamino)methanesulfonic acid Chemical compound OS(=O)(=O)CNC(=O)C=C KKSNTCYLMGYFFB-UHFFFAOYSA-N 0.000 description 1
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- ZORQXIQZAOLNGE-UHFFFAOYSA-N 1,1-difluorocyclohexane Chemical compound FC1(F)CCCCC1 ZORQXIQZAOLNGE-UHFFFAOYSA-N 0.000 description 1
- PQUXFUBNSYCQAL-UHFFFAOYSA-N 1-(2,3-difluorophenyl)ethanone Chemical compound CC(=O)C1=CC=CC(F)=C1F PQUXFUBNSYCQAL-UHFFFAOYSA-N 0.000 description 1
- QRIMLDXJAPZHJE-UHFFFAOYSA-N 2,3-dihydroxypropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(O)CO QRIMLDXJAPZHJE-UHFFFAOYSA-N 0.000 description 1
- OWPUOLBODXJOKH-UHFFFAOYSA-N 2,3-dihydroxypropyl prop-2-enoate Chemical compound OCC(O)COC(=O)C=C OWPUOLBODXJOKH-UHFFFAOYSA-N 0.000 description 1
- IEJPPSMHUUQABK-UHFFFAOYSA-N 2,4-diphenyl-4h-1,3-oxazol-5-one Chemical class O=C1OC(C=2C=CC=CC=2)=NC1C1=CC=CC=C1 IEJPPSMHUUQABK-UHFFFAOYSA-N 0.000 description 1
- SXGZJKUKBWWHRA-UHFFFAOYSA-N 2-(N-morpholiniumyl)ethanesulfonate Chemical compound [O-]S(=O)(=O)CC[NH+]1CCOCC1 SXGZJKUKBWWHRA-UHFFFAOYSA-N 0.000 description 1
- JKNCOURZONDCGV-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-methylprop-2-enoate Chemical compound CN(C)CCOC(=O)C(C)=C JKNCOURZONDCGV-UHFFFAOYSA-N 0.000 description 1
- DPBJAVGHACCNRL-UHFFFAOYSA-N 2-(dimethylamino)ethyl prop-2-enoate Chemical compound CN(C)CCOC(=O)C=C DPBJAVGHACCNRL-UHFFFAOYSA-N 0.000 description 1
- UVDYBBRVDUKNFV-UHFFFAOYSA-N 2-(prop-2-enoylamino)ethanesulfonic acid Chemical compound OS(=O)(=O)CCNC(=O)C=C UVDYBBRVDUKNFV-UHFFFAOYSA-N 0.000 description 1
- BBFOOZAYBHFYLK-UHFFFAOYSA-N 2-(prop-2-enoylamino)ethylphosphonic acid Chemical compound OP(O)(=O)CCNC(=O)C=C BBFOOZAYBHFYLK-UHFFFAOYSA-N 0.000 description 1
- 229920000536 2-Acrylamido-2-methylpropane sulfonic acid Polymers 0.000 description 1
- XHZPRMZZQOIPDS-UHFFFAOYSA-N 2-Methyl-2-[(1-oxo-2-propenyl)amino]-1-propanesulfonic acid Chemical compound OS(=O)(=O)CC(C)(C)NC(=O)C=C XHZPRMZZQOIPDS-UHFFFAOYSA-N 0.000 description 1
- ZTJNPDLOIVDEEL-UHFFFAOYSA-N 2-acetyloxyethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOC(C)=O ZTJNPDLOIVDEEL-UHFFFAOYSA-N 0.000 description 1
- UFIOPCXETLAGLR-UHFFFAOYSA-N 2-acetyloxyethyl prop-2-enoate Chemical compound CC(=O)OCCOC(=O)C=C UFIOPCXETLAGLR-UHFFFAOYSA-N 0.000 description 1
- VSZWLDAGOXQHNB-UHFFFAOYSA-M 2-aminoethyl(trimethyl)azanium;chloride Chemical class [Cl-].C[N+](C)(C)CCN VSZWLDAGOXQHNB-UHFFFAOYSA-M 0.000 description 1
- NEYTXADIGVEHQD-UHFFFAOYSA-N 2-hydroxy-2-(prop-2-enoylamino)acetic acid Chemical compound OC(=O)C(O)NC(=O)C=C NEYTXADIGVEHQD-UHFFFAOYSA-N 0.000 description 1
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 1
- TURITJIWSQEMDB-UHFFFAOYSA-N 2-methyl-n-[(2-methylprop-2-enoylamino)methyl]prop-2-enamide Chemical compound CC(=C)C(=O)NCNC(=O)C(C)=C TURITJIWSQEMDB-UHFFFAOYSA-N 0.000 description 1
- JDABGIQPZLWDFW-UHFFFAOYSA-N 2-methyl-n-[2-(2-methylprop-2-enoylamino)propyl]prop-2-enamide Chemical compound CC(=C)C(=O)NC(C)CNC(=O)C(C)=C JDABGIQPZLWDFW-UHFFFAOYSA-N 0.000 description 1
- YBKWKURHPIBUEM-UHFFFAOYSA-N 2-methyl-n-[6-(2-methylprop-2-enoylamino)hexyl]prop-2-enamide Chemical compound CC(=C)C(=O)NCCCCCCNC(=O)C(C)=C YBKWKURHPIBUEM-UHFFFAOYSA-N 0.000 description 1
- GTJOHISYCKPIMT-UHFFFAOYSA-N 2-methylundecane Chemical compound CCCCCCCCCC(C)C GTJOHISYCKPIMT-UHFFFAOYSA-N 0.000 description 1
- CEXQWAAGPPNOQF-UHFFFAOYSA-N 2-phenoxyethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOC1=CC=CC=C1 CEXQWAAGPPNOQF-UHFFFAOYSA-N 0.000 description 1
- ZQLCWFXMXMFGNE-UHFFFAOYSA-N 3-(2-methylprop-2-enoylamino)propylphosphonic acid Chemical compound CC(=C)C(=O)NCCCP(O)(O)=O ZQLCWFXMXMFGNE-UHFFFAOYSA-N 0.000 description 1
- SBWOBTUYQXLKSS-UHFFFAOYSA-N 3-(2-methylprop-2-enoyloxy)propanoic acid Chemical compound CC(=C)C(=O)OCCC(O)=O SBWOBTUYQXLKSS-UHFFFAOYSA-N 0.000 description 1
- WWJCRUKUIQRCGP-UHFFFAOYSA-N 3-(dimethylamino)propyl 2-methylprop-2-enoate Chemical compound CN(C)CCCOC(=O)C(C)=C WWJCRUKUIQRCGP-UHFFFAOYSA-N 0.000 description 1
- UFQHFMGRRVQFNA-UHFFFAOYSA-N 3-(dimethylamino)propyl prop-2-enoate Chemical compound CN(C)CCCOC(=O)C=C UFQHFMGRRVQFNA-UHFFFAOYSA-N 0.000 description 1
- YVAQHFNMILVVNE-UHFFFAOYSA-N 3-(prop-2-enoylamino)propanoic acid Chemical compound OC(=O)CCNC(=O)C=C YVAQHFNMILVVNE-UHFFFAOYSA-N 0.000 description 1
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- UZNHKBFIBYXPDV-UHFFFAOYSA-N trimethyl-[3-(2-methylprop-2-enoylamino)propyl]azanium;chloride Chemical compound [Cl-].CC(=C)C(=O)NCCC[N+](C)(C)C UZNHKBFIBYXPDV-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J39/00—Cation exchange; Use of material as cation exchangers; Treatment of material for improving the cation exchange properties
- B01J39/08—Use of material as cation exchangers; Treatment of material for improving the cation exchange properties
- B01J39/16—Organic material
- B01J39/18—Macromolecular compounds
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J39/00—Cation exchange; Use of material as cation exchangers; Treatment of material for improving the cation exchange properties
- B01J39/08—Use of material as cation exchangers; Treatment of material for improving the cation exchange properties
- B01J39/16—Organic material
- B01J39/18—Macromolecular compounds
- B01J39/20—Macromolecular compounds obtained by reactions only involving unsaturated carbon-to-carbon bonds
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/28—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof characterised by their form or physical properties
- B01J20/28054—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof characterised by their form or physical properties characterised by their surface properties or porosity
- B01J20/28078—Pore diameter
- B01J20/28085—Pore diameter being more than 50 nm, i.e. macropores
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J39/00—Cation exchange; Use of material as cation exchangers; Treatment of material for improving the cation exchange properties
- B01J39/08—Use of material as cation exchangers; Treatment of material for improving the cation exchange properties
- B01J39/16—Organic material
- B01J39/18—Macromolecular compounds
- B01J39/22—Cellulose or wood; Derivatives thereof
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J39/00—Cation exchange; Use of material as cation exchangers; Treatment of material for improving the cation exchange properties
- B01J39/26—Cation exchangers for chromatographic processes
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J41/00—Anion exchange; Use of material as anion exchangers; Treatment of material for improving the anion exchange properties
- B01J41/08—Use of material as anion exchangers; Treatment of material for improving the anion exchange properties
- B01J41/12—Macromolecular compounds
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J41/00—Anion exchange; Use of material as anion exchangers; Treatment of material for improving the anion exchange properties
- B01J41/08—Use of material as anion exchangers; Treatment of material for improving the anion exchange properties
- B01J41/12—Macromolecular compounds
- B01J41/14—Macromolecular compounds obtained by reactions only involving unsaturated carbon-to-carbon bonds
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J41/00—Anion exchange; Use of material as anion exchangers; Treatment of material for improving the anion exchange properties
- B01J41/20—Anion exchangers for chromatographic processes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/20—Manufacture of shaped structures of ion-exchange resins
-
- 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
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S526/00—Synthetic resins or natural rubbers -- part of the class 520 series
- Y10S526/909—Polymerization characterized by particle size of 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.]
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Analytical Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Nanotechnology (AREA)
- Manufacturing & Machinery (AREA)
- Materials Engineering (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
- Treatment Of Liquids With Adsorbents In General (AREA)
- Filtering Materials (AREA)
- Peptides Or Proteins (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10/849,700 US7098253B2 (en) | 2004-05-20 | 2004-05-20 | Macroporous ion exchange resins |
| US10/849,700 | 2004-05-20 | ||
| PCT/US2005/014469 WO2005115618A1 (en) | 2004-05-20 | 2005-04-27 | Macroporous ion exchange resins |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2008500172A JP2008500172A (ja) | 2008-01-10 |
| JP2008500172A5 JP2008500172A5 (enExample) | 2008-06-19 |
| JP4988574B2 true JP4988574B2 (ja) | 2012-08-01 |
Family
ID=34967600
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2007527250A Expired - Fee Related JP4988574B2 (ja) | 2004-05-20 | 2005-04-27 | マクロ孔質イオン交換樹脂 |
Country Status (6)
| Country | Link |
|---|---|
| US (2) | US7098253B2 (enExample) |
| EP (1) | EP1750839A1 (enExample) |
| JP (1) | JP4988574B2 (enExample) |
| KR (1) | KR20070015430A (enExample) |
| CN (1) | CN100577292C (enExample) |
| WO (1) | WO2005115618A1 (enExample) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7098253B2 (en) * | 2004-05-20 | 2006-08-29 | 3M Innovative Properties Company | Macroporous ion exchange resins |
| EP1807197A1 (en) * | 2004-10-01 | 2007-07-18 | 3M Innovative Properties Company | Composite filtration article |
| US7645312B2 (en) * | 2004-10-15 | 2010-01-12 | 3M Innovative Properties Company | Pleated multi-layer filter media and cartridge |
| DE102005020689B3 (de) * | 2005-05-03 | 2006-07-06 | Siemens Ag | Verfahren zur Herstellung einer Isolierplatte |
| US7674835B2 (en) * | 2005-12-21 | 2010-03-09 | 3M Innovative Properties Company | Method of making macroporous anion exchange resins |
| US7683100B2 (en) * | 2005-12-21 | 2010-03-23 | 3M Innovative Properties Company | Method of making macroporous cation exchange resins |
| US7674836B2 (en) * | 2006-07-28 | 2010-03-09 | 3M Innovative Properties Company | Method of making macroporous cation exchange resins |
| CN101678318B (zh) * | 2007-05-25 | 2013-09-25 | 默克专利股份公司 | 用于阳离子交换色谱法的接枝共聚物 |
| US8710111B2 (en) | 2007-11-09 | 2014-04-29 | 3M Innovative Properties Company | Porous polymeric resins |
| US8367198B2 (en) * | 2007-12-19 | 2013-02-05 | 3M Innovative Properties Company | Precisely-shaped porous particles |
| US20110006007A1 (en) * | 2008-02-12 | 2011-01-13 | Gokhan Kuruc | Composite polymeric filtration media |
| JP5867868B2 (ja) * | 2009-10-08 | 2016-02-24 | ジーイー・ヘルスケア・リミテッド | マルチストリーム高速液体クロマトグラフィーモジュール |
| GB0921951D0 (en) * | 2009-12-16 | 2010-02-03 | Fujifilm Mfg Europe Bv | Curable compositions and membranes |
| GB0921949D0 (en) | 2009-12-16 | 2010-02-03 | Fujifilm Mfg Europe Bv | Curable compositions and membranes |
| US9056316B2 (en) | 2010-06-25 | 2015-06-16 | 3M Innovative Properties Company | Semi-interpenetrating polymer network |
| CN105911183B (zh) * | 2011-02-10 | 2019-03-22 | 积水医疗株式会社 | 离子交换色谱法用填充剂以及核酸链的分离检测方法 |
| WO2012154314A1 (en) | 2011-03-31 | 2012-11-15 | 3M Innovative Properties Company | Method and device for indicating moisture based on bis (glyoxime) -transition metal complexes |
| GB201112382D0 (en) | 2011-07-19 | 2011-08-31 | Fujifilm Mfg Europe Bv | Curable compositions and membranes |
| WO2013147934A1 (en) | 2012-03-27 | 2013-10-03 | 3M Innovative Properties Company | Bis(glyoxime)-transition metal colorimetric moisture indicators |
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| WO2014078512A1 (en) | 2012-11-14 | 2014-05-22 | 3M Innovative Properties Company | Adjustable colorimetric moisture indicators |
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| WO2014150048A1 (en) | 2013-03-15 | 2014-09-25 | 3M Innovative Properties Company | Post-steam sterilization moisture-indicating articles |
| KR102092941B1 (ko) | 2013-06-12 | 2020-03-24 | 삼성전자주식회사 | 전기 흡착 탈이온 장치 및 이를 사용한 유체 처리 방법 |
| KR20160065093A (ko) * | 2013-08-23 | 2016-06-08 | 베링거 인겔하임 에르체파우 게엠베하 운트 코 카게 | 세포 파쇄 및/또는 생체분자 회수를 위한 미세입자 |
| JP6353057B2 (ja) * | 2013-09-17 | 2018-07-04 | ゼネラル・エレクトリック・カンパニイ | イオン交換ポリマー及びイオン交換ポリマーの製造方法 |
| CN105593276B (zh) | 2013-10-03 | 2020-03-27 | 3M创新有限公司 | 具有增强的结合容量的配体官能化基材 |
| KR102212322B1 (ko) | 2013-12-24 | 2021-02-03 | 삼성전자주식회사 | 전기 흡착 탈이온 전극, 그 제조 방법 및 이를 포함한 전기흡착 탈이온 장치 |
| WO2018048696A1 (en) | 2016-09-09 | 2018-03-15 | 3M Innovative Properties Company | Functionalized copolymers and use thereof |
| CN109689674A (zh) * | 2016-09-09 | 2019-04-26 | 3M创新有限公司 | 从生物溶液中的单体蛋白质分离聚集蛋白质的方法 |
| JP7308828B2 (ja) | 2017-11-16 | 2023-07-14 | スリーエム イノベイティブ プロパティズ カンパニー | 機能性粒子を含むポリマーマトリックス複合体及びその製造方法 |
| CN111357061B (zh) | 2017-11-16 | 2022-04-12 | 3M创新有限公司 | 包含介电粒子的聚合物基质复合材料及其制备方法 |
| US10927228B2 (en) | 2017-11-16 | 2021-02-23 | 3M Innovative Properties Company | Polymer matrix composites comprising intumescent particles and methods of making the same |
| US10913834B2 (en) | 2017-11-16 | 2021-02-09 | 3M Innovative Properties Company | Polymer matrix composites comprising indicator particles and methods of making the same |
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| US10737259B2 (en) | 2018-08-31 | 2020-08-11 | Pall Corporation | Salt tolerant anion exchange medium |
| US11045773B2 (en) | 2018-08-31 | 2021-06-29 | Pall Corporation | Salt tolerant porous medium |
| US12196727B2 (en) * | 2019-01-11 | 2025-01-14 | Eth Zurich | Device and method for detecting an analyte |
| WO2020159669A1 (en) | 2019-01-31 | 2020-08-06 | Dow Global Technologies Llc | Purification process for polyether-carbonate polyols |
| WO2021105843A1 (en) | 2019-11-25 | 2021-06-03 | 3M Innovative Properties Company | Biotin-containing monomers and articles formed therefrom |
| EP4136070B1 (en) | 2020-04-14 | 2024-05-29 | Solventum Intellectual Properties Company | Monomers, polymers, and articles for biomaterial capture |
| CN120418232A (zh) | 2022-12-21 | 2025-08-01 | 舒万诺知识产权公司 | 作为用于合成用于离子交换制品的聚合物的单体的杂环丙烯酸衍生物 |
| CN117003939B (zh) * | 2023-08-11 | 2024-12-03 | 中国铁工投资建设集团有限公司 | 一种吸附六价铬的弱碱性凝胶离子交换树脂及其制备方法 |
| CN117680108A (zh) * | 2023-12-11 | 2024-03-12 | 健帆生物科技集团股份有限公司 | 一种dna免疫吸附剂及其制备方法 |
| CN119613604B (zh) * | 2025-01-06 | 2025-11-18 | 山东星顺新材料有限公司 | 一种含磺酸结构羟甲基自交联型阳离子交换树脂及其制备方法和应用 |
| CN120205239B (zh) * | 2025-05-22 | 2025-08-12 | 西安蓝深新材料科技股份有限公司 | 一种离子交换树脂及其制备方法和应用 |
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| DE10033583A1 (de) | 2000-07-11 | 2002-01-24 | Bayer Ag | Superparamagnetische Perlpolymerisate |
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| FR2824734B1 (fr) * | 2001-05-16 | 2003-06-27 | Oreal | Composition pulverulente pour la decoloration des fibres keratiniques humaines |
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| FI20011575A0 (fi) * | 2001-07-26 | 2001-07-26 | Fortum Oyj | Polttoainekomponentit ja niiden selektiiviset valmistusmenetelmät |
| US7098253B2 (en) * | 2004-05-20 | 2006-08-29 | 3M Innovative Properties Company | Macroporous ion exchange resins |
| US7683100B2 (en) * | 2005-12-21 | 2010-03-23 | 3M Innovative Properties Company | Method of making macroporous cation exchange resins |
| US7674835B2 (en) * | 2005-12-21 | 2010-03-09 | 3M Innovative Properties Company | Method of making macroporous anion exchange resins |
-
2004
- 2004-05-20 US US10/849,700 patent/US7098253B2/en not_active Expired - Fee Related
-
2005
- 2005-02-17 US US11/059,858 patent/US7582684B2/en not_active Expired - Fee Related
- 2005-04-27 KR KR1020067024136A patent/KR20070015430A/ko not_active Withdrawn
- 2005-04-27 EP EP20050741114 patent/EP1750839A1/en not_active Withdrawn
- 2005-04-27 JP JP2007527250A patent/JP4988574B2/ja not_active Expired - Fee Related
- 2005-04-27 WO PCT/US2005/014469 patent/WO2005115618A1/en not_active Ceased
- 2005-04-27 CN CN200580016042A patent/CN100577292C/zh not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| US20050261384A1 (en) | 2005-11-24 |
| CN1956785A (zh) | 2007-05-02 |
| EP1750839A1 (en) | 2007-02-14 |
| JP2008500172A (ja) | 2008-01-10 |
| US20050261385A1 (en) | 2005-11-24 |
| US7582684B2 (en) | 2009-09-01 |
| WO2005115618A1 (en) | 2005-12-08 |
| KR20070015430A (ko) | 2007-02-02 |
| CN100577292C (zh) | 2010-01-06 |
| US7098253B2 (en) | 2006-08-29 |
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