CA2283292C - Hydrolytically stable resins for use in anion-exchange chromatography - Google Patents
Hydrolytically stable resins for use in anion-exchange chromatography Download PDFInfo
- Publication number
- CA2283292C CA2283292C CA002283292A CA2283292A CA2283292C CA 2283292 C CA2283292 C CA 2283292C CA 002283292 A CA002283292 A CA 002283292A CA 2283292 A CA2283292 A CA 2283292A CA 2283292 C CA2283292 C CA 2283292C
- Authority
- CA
- Canada
- Prior art keywords
- anion
- exchange
- group
- atoms
- linker
- 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 - Lifetime
Links
- 238000005571 anion exchange chromatography Methods 0.000 title claims description 24
- 229920005989 resin Polymers 0.000 title description 10
- 239000011347 resin Substances 0.000 title description 10
- 238000005349 anion exchange Methods 0.000 claims abstract description 107
- 239000000203 mixture Substances 0.000 claims abstract description 64
- 239000002245 particle Substances 0.000 claims abstract description 50
- 238000000034 method Methods 0.000 claims abstract description 44
- 229920003002 synthetic resin Polymers 0.000 claims abstract description 41
- 239000000057 synthetic resin Substances 0.000 claims abstract description 41
- 125000004429 atom Chemical group 0.000 claims abstract description 39
- 150000001875 compounds Chemical group 0.000 claims abstract description 39
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 26
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 23
- 150000002148 esters Chemical class 0.000 claims abstract description 10
- 125000003368 amide group Chemical group 0.000 claims abstract description 8
- 150000002576 ketones Chemical class 0.000 claims abstract description 7
- 229920000642 polymer Polymers 0.000 claims description 39
- 239000004816 latex Substances 0.000 claims description 31
- 229920000126 latex Polymers 0.000 claims description 31
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 31
- 239000000178 monomer Substances 0.000 claims description 27
- 125000004432 carbon atom Chemical group C* 0.000 claims description 20
- 239000003480 eluent Substances 0.000 claims description 19
- 150000001450 anions Chemical class 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 238000004587 chromatography analysis Methods 0.000 claims description 10
- 125000001424 substituent group Chemical group 0.000 claims description 9
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 239000001301 oxygen Substances 0.000 claims description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
- 125000004185 ester group Chemical group 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 229920006395 saturated elastomer Polymers 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 239000011593 sulfur Substances 0.000 claims description 4
- 125000004434 sulfur atom Chemical group 0.000 claims description 4
- 238000006467 substitution reaction Methods 0.000 claims description 3
- 150000001408 amides Chemical class 0.000 claims description 2
- 150000001721 carbon Chemical class 0.000 claims 2
- 230000003301 hydrolyzing effect Effects 0.000 abstract description 10
- 125000001453 quaternary ammonium group Chemical group 0.000 abstract description 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 abstract description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- 239000000243 solution Substances 0.000 description 27
- -1 compound glycidyl methacrylate Chemical class 0.000 description 19
- 125000005647 linker group Chemical group 0.000 description 19
- 230000005526 G1 to G0 transition Effects 0.000 description 18
- 239000002270 dispersing agent Substances 0.000 description 18
- 230000015572 biosynthetic process Effects 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 11
- 238000006116 polymerization reaction Methods 0.000 description 11
- 238000002360 preparation method Methods 0.000 description 11
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 10
- 150000002118 epoxides Chemical group 0.000 description 10
- 238000003786 synthesis reaction Methods 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 9
- 229920001577 copolymer Polymers 0.000 description 9
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 8
- 125000005843 halogen group Chemical group 0.000 description 8
- 125000005842 heteroatom Chemical group 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 8
- QWDCNUDLDABORJ-UHFFFAOYSA-N 2-(oxiran-2-ylmethoxy)ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCC1CO1 QWDCNUDLDABORJ-UHFFFAOYSA-N 0.000 description 7
- 239000002243 precursor Substances 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 5
- 230000007062 hydrolysis Effects 0.000 description 5
- 238000006460 hydrolysis reaction Methods 0.000 description 5
- 230000014759 maintenance of location Effects 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
- 150000003512 tertiary amines Chemical class 0.000 description 5
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 4
- XFCMNSHQOZQILR-UHFFFAOYSA-N 2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOC(=O)C(C)=C XFCMNSHQOZQILR-UHFFFAOYSA-N 0.000 description 4
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 238000005054 agglomeration Methods 0.000 description 4
- 230000002776 aggregation Effects 0.000 description 4
- 238000004132 cross linking Methods 0.000 description 4
- 239000002609 medium Substances 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- PTBAHIRKWPUZAM-UHFFFAOYSA-N 2-(oxiran-2-yl)ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCC1CO1 PTBAHIRKWPUZAM-UHFFFAOYSA-N 0.000 description 3
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 3
- 229920001732 Lignosulfonate Polymers 0.000 description 3
- 150000003863 ammonium salts Chemical group 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 3
- 239000003999 initiator Substances 0.000 description 3
- 235000019357 lignosulphonate Nutrition 0.000 description 3
- 230000007246 mechanism Effects 0.000 description 3
- MKOQAXOMCIQUJY-UHFFFAOYSA-N pent-4-enyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCC=C MKOQAXOMCIQUJY-UHFFFAOYSA-N 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- JEZHVHRYCXYZIJ-UHFFFAOYSA-N 1-(oxiran-2-yl)propan-2-yl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(C)CC1CO1 JEZHVHRYCXYZIJ-UHFFFAOYSA-N 0.000 description 2
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 2
- UAYUPCNOUDRHFB-UHFFFAOYSA-N 2-[2-(dimethylamino)ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CN(C)CCOCCOC(=O)C(C)=C UAYUPCNOUDRHFB-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 229920000084 Gum arabic Polymers 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 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
- 239000004372 Polyvinyl alcohol Substances 0.000 description 2
- 241000978776 Senegalia senegal Species 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000000205 acacia gum Substances 0.000 description 2
- 235000010489 acacia gum Nutrition 0.000 description 2
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 2
- 239000012736 aqueous medium Substances 0.000 description 2
- LXGTYUAXSYBVFR-UHFFFAOYSA-N but-3-enyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCC=C LXGTYUAXSYBVFR-UHFFFAOYSA-N 0.000 description 2
- 125000003636 chemical group Chemical group 0.000 description 2
- 238000013375 chromatographic separation Methods 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 238000006735 epoxidation reaction Methods 0.000 description 2
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Chemical compound CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 238000007306 functionalization reaction Methods 0.000 description 2
- 238000010348 incorporation Methods 0.000 description 2
- 230000002427 irreversible effect Effects 0.000 description 2
- 229920005610 lignin Polymers 0.000 description 2
- CRGZYKWWYNQGEC-UHFFFAOYSA-N magnesium;methanolate Chemical compound [Mg+2].[O-]C.[O-]C CRGZYKWWYNQGEC-UHFFFAOYSA-N 0.000 description 2
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- XFTBMMBBOQOUFS-UHFFFAOYSA-N pent-4-en-2-yl 2-methylprop-2-enoate Chemical compound C=CCC(C)OC(=O)C(C)=C XFTBMMBBOQOUFS-UHFFFAOYSA-N 0.000 description 2
- 229950000688 phenothiazine Drugs 0.000 description 2
- 229920002451 polyvinyl alcohol Polymers 0.000 description 2
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 2
- 239000012451 post-reaction mixture Substances 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 238000012552 review Methods 0.000 description 2
- 239000007790 solid phase Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000010557 suspension polymerization reaction Methods 0.000 description 2
- IGGDKDTUCAWDAN-UHFFFAOYSA-N 1-vinylnaphthalene Chemical compound C1=CC=C2C(C=C)=CC=CC2=C1 IGGDKDTUCAWDAN-UHFFFAOYSA-N 0.000 description 1
- YSAANLSYLSUVHB-UHFFFAOYSA-N 2-[2-(dimethylamino)ethoxy]ethanol Chemical compound CN(C)CCOCCO YSAANLSYLSUVHB-UHFFFAOYSA-N 0.000 description 1
- SBYMUDUGTIKLCR-UHFFFAOYSA-N 2-chloroethenylbenzene Chemical compound ClC=CC1=CC=CC=C1 SBYMUDUGTIKLCR-UHFFFAOYSA-N 0.000 description 1
- SFPNZPQIIAJXGL-UHFFFAOYSA-N 2-ethoxyethyl 2-methylprop-2-enoate Chemical compound CCOCCOC(=O)C(C)=C SFPNZPQIIAJXGL-UHFFFAOYSA-N 0.000 description 1
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical compound C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 description 1
- PYSRRFNXTXNWCD-UHFFFAOYSA-N 3-(2-phenylethenyl)furan-2,5-dione Chemical compound O=C1OC(=O)C(C=CC=2C=CC=CC=2)=C1 PYSRRFNXTXNWCD-UHFFFAOYSA-N 0.000 description 1
- HRSPJFPORLWKHP-UHFFFAOYSA-N 3-(oxiran-2-yl)propyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCC1CO1 HRSPJFPORLWKHP-UHFFFAOYSA-N 0.000 description 1
- ZSPTYLOMNJNZNG-UHFFFAOYSA-N 3-Buten-1-ol Chemical compound OCCC=C ZSPTYLOMNJNZNG-UHFFFAOYSA-N 0.000 description 1
- IWTYTFSSTWXZFU-UHFFFAOYSA-N 3-chloroprop-1-enylbenzene Chemical compound ClCC=CC1=CC=CC=C1 IWTYTFSSTWXZFU-UHFFFAOYSA-N 0.000 description 1
- DBCAQXHNJOFNGC-UHFFFAOYSA-N 4-bromo-1,1,1-trifluorobutane Chemical compound FC(F)(F)CCCBr DBCAQXHNJOFNGC-UHFFFAOYSA-N 0.000 description 1
- NUXLDNTZFXDNBA-UHFFFAOYSA-N 6-bromo-2-methyl-4h-1,4-benzoxazin-3-one Chemical compound C1=C(Br)C=C2NC(=O)C(C)OC2=C1 NUXLDNTZFXDNBA-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 239000004971 Cross linker Substances 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
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- 229920002845 Poly(methacrylic acid) Polymers 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- 229920000147 Styrene maleic anhydride Polymers 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
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- 238000013019 agitation Methods 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
- 238000005576 amination reaction Methods 0.000 description 1
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- 125000003118 aryl group Chemical group 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
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- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000013626 chemical specie Substances 0.000 description 1
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- 238000010276 construction Methods 0.000 description 1
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- 239000008367 deionised water Substances 0.000 description 1
- 230000002939 deleterious effect Effects 0.000 description 1
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- 238000005516 engineering process Methods 0.000 description 1
- YPFKALGSDMYUGV-UHFFFAOYSA-M ethyl-dimethyl-[2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethyl]azanium;bromide Chemical compound [Br-].CC[N+](C)(C)CCOCCOC(=O)C(C)=C YPFKALGSDMYUGV-UHFFFAOYSA-M 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
- 229920000578 graft copolymer Polymers 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 150000002431 hydrogen Chemical group 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 125000005395 methacrylic acid group Chemical group 0.000 description 1
- VHRYZQNGTZXDNX-UHFFFAOYSA-N methacryloyl chloride Chemical compound CC(=C)C(Cl)=O VHRYZQNGTZXDNX-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 229940111688 monobasic potassium phosphate Drugs 0.000 description 1
- 235000019796 monopotassium phosphate Nutrition 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- LQAVWYMTUMSFBE-UHFFFAOYSA-N pent-4-en-1-ol Chemical compound OCCCC=C LQAVWYMTUMSFBE-UHFFFAOYSA-N 0.000 description 1
- ZHZCYWWNFQUZOR-UHFFFAOYSA-N pent-4-en-2-ol Chemical compound CC(O)CC=C ZHZCYWWNFQUZOR-UHFFFAOYSA-N 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- GNSKLFRGEWLPPA-UHFFFAOYSA-M potassium dihydrogen phosphate Chemical compound [K+].OP(O)([O-])=O GNSKLFRGEWLPPA-UHFFFAOYSA-M 0.000 description 1
- RWPGFSMJFRPDDP-UHFFFAOYSA-L potassium metabisulfite Chemical compound [K+].[K+].[O-]S(=O)S([O-])(=O)=O RWPGFSMJFRPDDP-UHFFFAOYSA-L 0.000 description 1
- 229940043349 potassium metabisulfite Drugs 0.000 description 1
- 235000010263 potassium metabisulphite Nutrition 0.000 description 1
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 238000007348 radical reaction Methods 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 229940117958 vinyl acetate Drugs 0.000 description 1
- 239000011800 void material Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/44—Preparation of metal salts or ammonium salts
Landscapes
- Chemical & Material Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Treatment Of Liquids With Adsorbents In General (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
- Manufacture Of Macromolecular Shaped Articles (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/805,858 | 1997-03-03 | ||
| US08/805,858 US5936003A (en) | 1997-03-03 | 1997-03-03 | Hydrolytically stable resins for use in anion-exchange chromatography |
| PCT/US1998/004101 WO1998039367A1 (en) | 1997-03-03 | 1998-03-03 | Hydrolytically stable resins for use in anion-exchange chromatography |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2283292A1 CA2283292A1 (en) | 1998-09-11 |
| CA2283292C true CA2283292C (en) | 2008-10-14 |
Family
ID=25192705
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002283292A Expired - Lifetime CA2283292C (en) | 1997-03-03 | 1998-03-03 | Hydrolytically stable resins for use in anion-exchange chromatography |
Country Status (8)
| Country | Link |
|---|---|
| US (2) | US5936003A (enExample) |
| EP (1) | EP0964878B1 (enExample) |
| JP (1) | JP4253714B2 (enExample) |
| AT (1) | ATE373021T1 (enExample) |
| AU (1) | AU739151B2 (enExample) |
| CA (1) | CA2283292C (enExample) |
| DE (1) | DE69838418T2 (enExample) |
| WO (1) | WO1998039367A1 (enExample) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6077421A (en) * | 1996-07-18 | 2000-06-20 | The United States Of America As Represented By The Secretary Of The Navy | Metal complexing |
| US6881761B2 (en) * | 2000-05-29 | 2005-04-19 | Showa Denko K.K. | Porous polymer particle, anion exchanger, producing method thereof, column for ion chromatography, and method for measuring anions |
| JP4651178B2 (ja) * | 2000-10-23 | 2011-03-16 | 三菱レイヨン株式会社 | ２−グリシジルオキシエチル（メタ）アクリレートの製造方法 |
| US20020194901A1 (en) * | 2000-12-19 | 2002-12-26 | Showa Denko K.K. | Porous polymer particle, alkali-resistant anion exchanger, producing method thereof, column for ion chromatography, and method for measuring anions |
| US20030066336A1 (en) * | 2000-12-19 | 2003-04-10 | Showa Denko K.K. | Method for measuring anions |
| CN100512951C (zh) * | 2004-07-09 | 2009-07-15 | 株式会社阿库泰克 | 铟吸附剂以及铟分离方法 |
| US20070034572A1 (en) * | 2005-08-09 | 2007-02-15 | The Procter & Gamble Company | Low pressure anion chromatographic apparatus and method having two or more eluents |
| US9314712B2 (en) * | 2008-05-09 | 2016-04-19 | Dionex Corporation | Functionalized substrates with ion-exchange properties |
| EP2571591B1 (en) | 2010-05-19 | 2017-08-02 | Dionex Corporation | Functionalized substrates with aromatic stacking properties |
| WO2012112553A1 (en) | 2011-02-14 | 2012-08-23 | Dionex Corporation | Nanometer size chemical modified materials and uses |
| US9310344B2 (en) | 2013-06-14 | 2016-04-12 | Dionex Corporation | HILIC/anion-exchange/cation-exchange multimodal media |
| EP2745904B1 (en) | 2012-12-21 | 2015-12-16 | Dionex Corporation | HILIC/Anion-Exchange/Cation-Exchange Multimodal Media |
| US9169331B2 (en) | 2012-12-21 | 2015-10-27 | Dionex Corporation | Separation of glycans by mixed-mode liquid chromatography |
| US10641751B2 (en) | 2015-06-19 | 2020-05-05 | Dionex Corporation | Ion exchange chromatography column, method, and system thereof |
| US10118171B2 (en) * | 2015-07-30 | 2018-11-06 | Dionex Corporation | Ion-exchange composition comprising a complex of support particles, dispersant, and electrostatically bound layering particles |
| US10379090B2 (en) | 2016-06-17 | 2019-08-13 | Dionex Corporation | Charge reversible ion exchange resins, chromatography column, method, and system thereof |
| US10814319B2 (en) | 2016-09-30 | 2020-10-27 | Board Of Regents, University Of Texas System | Functionalized polyolefin capillaries for open tubular ion chromatography |
Family Cites Families (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB835550A (en) * | 1955-03-21 | 1960-05-25 | Rohm & Haas | Quaternary ammonium copolymers and methods of producing them |
| US3001975A (en) * | 1957-04-05 | 1961-09-26 | Rohm & Haas | Monoepoxidation of esters, monomers, and polymers thereof |
| US3228920A (en) * | 1960-05-12 | 1966-01-11 | Metal Recovery Systems | Chelating resins and method of preparation |
| CS187563B1 (en) * | 1974-02-08 | 1979-02-28 | Petr Strop | Method of preparation of the hydrophilic homogeneous or macroporous annexes |
| US4082564A (en) * | 1975-09-09 | 1978-04-04 | Rohm And Haas Company | Sugar decolorizing quaternary ammonium acrylamide resins |
| SE405549B (sv) * | 1975-10-09 | 1978-12-18 | Pharmacia Fine Chemicals Ab | Forfarande for isolering av albumin ur plasmaprodukter genom kromatografisk fraktionering |
| US4118316A (en) * | 1976-10-13 | 1978-10-03 | Calgon Corporation | Quaternized siliceous supports for gel permeation chromatography |
| IT1123619B (it) * | 1976-11-11 | 1986-04-30 | Anic Spa | Processo per la produzione di polimeri contenenti gruppi amminici liberi o salificati e gruppi ammonici quaternari,e prodotti relativi |
| EP0187281B1 (en) * | 1985-01-07 | 1993-06-23 | Rhone-Poulenc Specialty Chemicals Co. | Novel carboxylate polymers and processes for their preparation and use |
| DE3543348A1 (de) * | 1985-12-07 | 1987-06-11 | Bayer Ag | Perlfoermige vernetzte, epoxy- und basische aminogruppen aufweisende mischpolymerisate, verfahren zu ihrer herstellung und ihre verwendung |
| NL8701915A (nl) * | 1987-08-14 | 1989-03-01 | Waander Riethorst | Adsorbensmateriaal en toepassing daarvan voor het isoleren van stollingsfaktoren. |
| US5230885A (en) * | 1987-12-23 | 1993-07-27 | Smith Kline & French Laboratories Limited | Polystyrene anion exchange polymer pharmaceutical composition |
| GB8829088D0 (en) * | 1988-12-13 | 1989-01-25 | Smith Kline French Lab | Compounds |
| GB8911719D0 (en) * | 1989-05-22 | 1989-07-05 | Smith Kline French Lab | Compounds |
| SE8902315D0 (sv) * | 1989-06-27 | 1989-06-27 | Pharmacia Ab | Anjonbytare |
| US5250602A (en) * | 1990-01-31 | 1993-10-05 | Mitsui-Cyanamid, Ltd. | Polymer emulsion and method for preparing the same |
| US5350523A (en) * | 1990-02-28 | 1994-09-27 | Mitsubishi Kasei Corporation | Anion exchange method |
| US5137925A (en) * | 1991-03-11 | 1992-08-11 | Ionics, Incorporated | Aliphatic anion exchange polymeric membranes having improved resistance to fouling |
| US5372719A (en) * | 1992-03-30 | 1994-12-13 | Perseptive Biosystems, Inc. | Molecular imaging |
| US5503933A (en) * | 1994-02-25 | 1996-04-02 | Purdue Research Foundation | Covalently bonded coatings |
-
1997
- 1997-03-03 US US08/805,858 patent/US5936003A/en not_active Expired - Lifetime
-
1998
- 1998-01-30 US US09/016,578 patent/US5925253A/en not_active Expired - Lifetime
- 1998-03-03 DE DE69838418T patent/DE69838418T2/de not_active Expired - Lifetime
- 1998-03-03 JP JP53868498A patent/JP4253714B2/ja not_active Expired - Lifetime
- 1998-03-03 AT AT98910133T patent/ATE373021T1/de not_active IP Right Cessation
- 1998-03-03 AU AU64448/98A patent/AU739151B2/en not_active Expired
- 1998-03-03 WO PCT/US1998/004101 patent/WO1998039367A1/en not_active Ceased
- 1998-03-03 EP EP98910133A patent/EP0964878B1/en not_active Expired - Lifetime
- 1998-03-03 CA CA002283292A patent/CA2283292C/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| EP0964878A4 (en) | 2004-12-22 |
| WO1998039367A1 (en) | 1998-09-11 |
| US5936003A (en) | 1999-08-10 |
| EP0964878A1 (en) | 1999-12-22 |
| JP2001511256A (ja) | 2001-08-07 |
| DE69838418T2 (de) | 2008-06-12 |
| CA2283292A1 (en) | 1998-09-11 |
| DE69838418D1 (de) | 2007-10-25 |
| EP0964878B1 (en) | 2007-09-12 |
| JP4253714B2 (ja) | 2009-04-15 |
| AU739151B2 (en) | 2001-10-04 |
| US5925253A (en) | 1999-07-20 |
| AU6444898A (en) | 1998-09-22 |
| ATE373021T1 (de) | 2007-09-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKEX | Expiry |
Effective date: 20180305 |