HU213523B - Process for producing crosslinked copolymers predominantly comprising units formed from methacrylic anhydride and process using said copolymers for adsorption, ion exchange or affinity chromatography and adsorbing of proteins - Google Patents
Process for producing crosslinked copolymers predominantly comprising units formed from methacrylic anhydride and process using said copolymers for adsorption, ion exchange or affinity chromatography and adsorbing of proteins Download PDFInfo
- Publication number
- HU213523B HU213523B HU9301586A HU9301586A HU213523B HU 213523 B HU213523 B HU 213523B HU 9301586 A HU9301586 A HU 9301586A HU 9301586 A HU9301586 A HU 9301586A HU 213523 B HU213523 B HU 213523B
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- HU
- Hungary
- Prior art keywords
- beads
- functional groups
- process according
- copolymer
- initiator
- Prior art date
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- 238000000034 method Methods 0.000 title claims abstract description 71
- 229920001577 copolymer Polymers 0.000 title claims abstract description 70
- DCUFMVPCXCSVNP-UHFFFAOYSA-N methacrylic anhydride Chemical compound CC(=C)C(=O)OC(=O)C(C)=C DCUFMVPCXCSVNP-UHFFFAOYSA-N 0.000 title claims abstract description 28
- 238000001042 affinity chromatography Methods 0.000 title claims abstract description 6
- 102000004169 proteins and genes Human genes 0.000 title claims description 14
- 108090000623 proteins and genes Proteins 0.000 title claims description 14
- 238000005377 adsorption chromatography Methods 0.000 title claims description 4
- 238000004255 ion exchange chromatography Methods 0.000 title claims description 4
- 239000011324 bead Substances 0.000 claims abstract description 90
- 239000002253 acid Substances 0.000 claims abstract description 14
- 238000002360 preparation method Methods 0.000 claims abstract description 14
- 239000000178 monomer Substances 0.000 claims description 76
- 239000003999 initiator Substances 0.000 claims description 26
- 239000000203 mixture Substances 0.000 claims description 21
- 238000004132 cross linking Methods 0.000 claims description 18
- 238000006116 polymerization reaction Methods 0.000 claims description 17
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 claims description 16
- 239000002245 particle Substances 0.000 claims description 16
- -1 polyethylene Polymers 0.000 claims description 14
- 239000011148 porous material Substances 0.000 claims description 14
- 239000003361 porogen Substances 0.000 claims description 12
- 239000007900 aqueous suspension Substances 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 125000000524 functional group Chemical group 0.000 claims description 9
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 claims description 8
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 claims description 8
- 125000001931 aliphatic group Chemical group 0.000 claims description 8
- NOBYOEQUFMGXBP-UHFFFAOYSA-N (4-tert-butylcyclohexyl) (4-tert-butylcyclohexyl)oxycarbonyloxy carbonate Chemical compound C1CC(C(C)(C)C)CCC1OC(=O)OOC(=O)OC1CCC(C(C)(C)C)CC1 NOBYOEQUFMGXBP-UHFFFAOYSA-N 0.000 claims description 7
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 7
- 150000003863 ammonium salts Chemical group 0.000 claims description 7
- 229940057404 di-(4-tert-butylcyclohexyl)peroxydicarbonate Drugs 0.000 claims description 7
- 150000002148 esters Chemical class 0.000 claims description 7
- 239000007788 liquid Substances 0.000 claims description 7
- 150000003254 radicals Chemical class 0.000 claims description 7
- KUDUQBURMYMBIJ-UHFFFAOYSA-N 2-prop-2-enoyloxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC(=O)C=C KUDUQBURMYMBIJ-UHFFFAOYSA-N 0.000 claims description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- 150000001732 carboxylic acid derivatives Chemical group 0.000 claims description 6
- 150000002978 peroxides Chemical group 0.000 claims description 6
- 239000003505 polymerization initiator Substances 0.000 claims description 6
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 claims description 6
- NUIZZJWNNGJSGL-UHFFFAOYSA-N 2-phenylpropan-2-yl 2,2-dimethyloctaneperoxoate Chemical compound CCCCCCC(C)(C)C(=O)OOC(C)(C)c1ccccc1 NUIZZJWNNGJSGL-UHFFFAOYSA-N 0.000 claims description 5
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 claims description 5
- 238000000354 decomposition reaction Methods 0.000 claims description 5
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetraline Natural products C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 claims description 5
- OVBFMEVBMNZIBR-UHFFFAOYSA-N -2-Methylpentanoic acid Natural products CCCC(C)C(O)=O OVBFMEVBMNZIBR-UHFFFAOYSA-N 0.000 claims description 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 4
- 150000001408 amides Chemical class 0.000 claims description 4
- 239000007864 aqueous solution Substances 0.000 claims description 4
- ZQMIGQNCOMNODD-UHFFFAOYSA-N diacetyl peroxide Chemical compound CC(=O)OOC(C)=O ZQMIGQNCOMNODD-UHFFFAOYSA-N 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- KHAHWKLZGBIAKT-UHFFFAOYSA-N 4-(4-methylpyrimidin-2-yl)benzaldehyde Chemical compound CC1=CC=NC(C=2C=CC(C=O)=CC=2)=N1 KHAHWKLZGBIAKT-UHFFFAOYSA-N 0.000 claims description 3
- DBCAQXHNJOFNGC-UHFFFAOYSA-N 4-bromo-1,1,1-trifluorobutane Chemical compound FC(F)(F)CCCBr DBCAQXHNJOFNGC-UHFFFAOYSA-N 0.000 claims description 3
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 3
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 claims description 3
- 239000004698 Polyethylene Substances 0.000 claims description 3
- ZPOLOEWJWXZUSP-AATRIKPKSA-N bis(prop-2-enyl) (e)-but-2-enedioate Chemical compound C=CCOC(=O)\C=C\C(=O)OCC=C ZPOLOEWJWXZUSP-AATRIKPKSA-N 0.000 claims description 3
- ZPOLOEWJWXZUSP-WAYWQWQTSA-N bis(prop-2-enyl) (z)-but-2-enedioate Chemical compound C=CCOC(=O)\C=C/C(=O)OCC=C ZPOLOEWJWXZUSP-WAYWQWQTSA-N 0.000 claims description 3
- HABAXTXIECRCKH-UHFFFAOYSA-N bis(prop-2-enyl) butanedioate Chemical compound C=CCOC(=O)CCC(=O)OCC=C HABAXTXIECRCKH-UHFFFAOYSA-N 0.000 claims description 3
- JKJWYKGYGWOAHT-UHFFFAOYSA-N bis(prop-2-enyl) carbonate Chemical compound C=CCOC(=O)OCC=C JKJWYKGYGWOAHT-UHFFFAOYSA-N 0.000 claims description 3
- FPODCVUTIPDRTE-UHFFFAOYSA-N bis(prop-2-enyl) hexanedioate Chemical compound C=CCOC(=O)CCCCC(=O)OCC=C FPODCVUTIPDRTE-UHFFFAOYSA-N 0.000 claims description 3
- BKXRKRANFLFTFU-UHFFFAOYSA-N bis(prop-2-enyl) oxalate Chemical compound C=CCOC(=O)C(=O)OCC=C BKXRKRANFLFTFU-UHFFFAOYSA-N 0.000 claims description 3
- AOESAXAWXYJFNC-UHFFFAOYSA-N bis(prop-2-enyl) propanedioate Chemical compound C=CCOC(=O)CC(=O)OCC=C AOESAXAWXYJFNC-UHFFFAOYSA-N 0.000 claims description 3
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 claims description 3
- HJWBBBADPXPUPA-UHFFFAOYSA-N ethyl 3-(4-chlorophenyl)-5-methyl-1,2-oxazole-4-carboxylate Chemical compound CCOC(=O)C1=C(C)ON=C1C1=CC=C(Cl)C=C1 HJWBBBADPXPUPA-UHFFFAOYSA-N 0.000 claims description 3
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- 150000002825 nitriles Chemical class 0.000 claims description 3
- 229920000573 polyethylene Polymers 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- QTECDUFMBMSHKR-UHFFFAOYSA-N prop-2-enyl prop-2-enoate Chemical compound C=CCOC(=O)C=C QTECDUFMBMSHKR-UHFFFAOYSA-N 0.000 claims description 3
- 239000000376 reactant Substances 0.000 claims description 3
- 239000008096 xylene Substances 0.000 claims description 3
- WVAFEFUPWRPQSY-UHFFFAOYSA-N 1,2,3-tris(ethenyl)benzene Chemical compound C=CC1=CC=CC(C=C)=C1C=C WVAFEFUPWRPQSY-UHFFFAOYSA-N 0.000 claims description 2
- ZJQIXGGEADDPQB-UHFFFAOYSA-N 1,2-bis(ethenyl)-3,4-dimethylbenzene Chemical group CC1=CC=C(C=C)C(C=C)=C1C ZJQIXGGEADDPQB-UHFFFAOYSA-N 0.000 claims description 2
- YKKDJUGGSDWUKX-UHFFFAOYSA-N 1,2-bis(ethenyl)-3-ethylbenzene Chemical compound CCC1=CC=CC(C=C)=C1C=C YKKDJUGGSDWUKX-UHFFFAOYSA-N 0.000 claims description 2
- QLLUAUADIMPKIH-UHFFFAOYSA-N 1,2-bis(ethenyl)naphthalene Chemical class C1=CC=CC2=C(C=C)C(C=C)=CC=C21 QLLUAUADIMPKIH-UHFFFAOYSA-N 0.000 claims description 2
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 claims description 2
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 claims description 2
- WFUGQJXVXHBTEM-UHFFFAOYSA-N 2-hydroperoxy-2-(2-hydroperoxybutan-2-ylperoxy)butane Chemical compound CCC(C)(OO)OOC(C)(CC)OO WFUGQJXVXHBTEM-UHFFFAOYSA-N 0.000 claims description 2
- WVYWICLMDOOCFB-UHFFFAOYSA-N 4-methyl-2-pentanol Chemical compound CC(C)CC(C)O WVYWICLMDOOCFB-UHFFFAOYSA-N 0.000 claims description 2
- 239000004342 Benzoyl peroxide Substances 0.000 claims description 2
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical group C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 claims description 2
- 239000004641 Diallyl-phthalate Substances 0.000 claims description 2
- ZRYCZAWRXHAAPZ-UHFFFAOYSA-N alpha,alpha-dimethyl valeric acid Chemical compound CCCC(C)(C)C(O)=O ZRYCZAWRXHAAPZ-UHFFFAOYSA-N 0.000 claims description 2
- 235000019400 benzoyl peroxide Nutrition 0.000 claims description 2
- QUDWYFHPNIMBFC-UHFFFAOYSA-N bis(prop-2-enyl) benzene-1,2-dicarboxylate Chemical compound C=CCOC(=O)C1=CC=CC=C1C(=O)OCC=C QUDWYFHPNIMBFC-UHFFFAOYSA-N 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- XJOBOFWTZOKMOH-UHFFFAOYSA-N decanoyl decaneperoxoate Chemical compound CCCCCCCCCC(=O)OOC(=O)CCCCCCCCC XJOBOFWTZOKMOH-UHFFFAOYSA-N 0.000 claims description 2
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- QZYRMODBFHTNHF-UHFFFAOYSA-N ditert-butyl benzene-1,2-dicarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1C(=O)OOC(C)(C)C QZYRMODBFHTNHF-UHFFFAOYSA-N 0.000 claims description 2
- 150000002576 ketones Chemical class 0.000 claims description 2
- DBSDMAPJGHBWAL-UHFFFAOYSA-N penta-1,4-dien-3-ylbenzene Chemical class C=CC(C=C)C1=CC=CC=C1 DBSDMAPJGHBWAL-UHFFFAOYSA-N 0.000 claims description 2
- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 claims description 2
- UAXOELSVPTZZQG-UHFFFAOYSA-N tiglic acid Natural products CC(C)=C(C)C(O)=O UAXOELSVPTZZQG-UHFFFAOYSA-N 0.000 claims description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims 2
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical group C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 claims 2
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 229920000642 polymer Polymers 0.000 abstract description 19
- 150000008064 anhydrides Chemical group 0.000 abstract description 14
- 239000000463 material Substances 0.000 abstract description 4
- 239000003456 ion exchange resin Substances 0.000 abstract description 3
- 229920003303 ion-exchange polymer Polymers 0.000 abstract description 3
- 239000002243 precursor Substances 0.000 abstract description 2
- 239000011347 resin Substances 0.000 description 25
- 229920005989 resin Polymers 0.000 description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- 102100030497 Cytochrome c Human genes 0.000 description 17
- 108010075031 Cytochromes c Proteins 0.000 description 17
- 239000011541 reaction mixture Substances 0.000 description 17
- 239000000243 solution Substances 0.000 description 16
- 239000012071 phase Substances 0.000 description 13
- UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- 150000001412 amines Chemical class 0.000 description 10
- 239000008367 deionised water Substances 0.000 description 10
- 229910021641 deionized water Inorganic materials 0.000 description 10
- 239000000523 sample Substances 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000012508 resin bead Substances 0.000 description 9
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
- 239000008346 aqueous phase Substances 0.000 description 8
- 229940043265 methyl isobutyl ketone Drugs 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 229960005322 streptomycin Drugs 0.000 description 6
- 239000004971 Cross linker Substances 0.000 description 5
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 5
- 230000002378 acidificating effect Effects 0.000 description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 5
- 125000002843 carboxylic acid group Chemical group 0.000 description 5
- 239000003208 petroleum Substances 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 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 4
- 239000008351 acetate buffer Substances 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000002002 slurry Substances 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 238000010557 suspension polymerization reaction Methods 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 3
- 238000002835 absorbance Methods 0.000 description 3
- 239000003463 adsorbent Substances 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 238000009826 distribution Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 238000005342 ion exchange Methods 0.000 description 3
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- AGGKEGLBGGJEBZ-UHFFFAOYSA-N tetramethylenedisulfotetramine Chemical compound C1N(S2(=O)=O)CN3S(=O)(=O)N1CN2C3 AGGKEGLBGGJEBZ-UHFFFAOYSA-N 0.000 description 3
- NXVGUNGPINUNQN-UHFFFAOYSA-N 2-phenylpropan-2-yl 7,7-dimethyloctaneperoxoate Chemical compound CC(C)(C)CCCCCC(=O)OOC(C)(C)C1=CC=CC=C1 NXVGUNGPINUNQN-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 108010006654 Bleomycin Proteins 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group 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 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- 208000025865 Ulcer Diseases 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 229960001561 bleomycin Drugs 0.000 description 2
- MPMBRWOOISTHJV-UHFFFAOYSA-N but-1-enylbenzene Chemical compound CCC=CC1=CC=CC=C1 MPMBRWOOISTHJV-UHFFFAOYSA-N 0.000 description 2
- 238000005341 cation exchange Methods 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 238000007306 functionalization reaction Methods 0.000 description 2
- 230000002209 hydrophobic effect Effects 0.000 description 2
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 125000005397 methacrylic acid ester group Chemical group 0.000 description 2
- 229940078552 o-xylene Drugs 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 238000006053 organic reaction Methods 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 239000006228 supernatant Substances 0.000 description 2
- 150000003573 thiols Chemical class 0.000 description 2
- 231100000397 ulcer Toxicity 0.000 description 2
- BEQKKZICTDFVMG-UHFFFAOYSA-N 1,2,3,4,6-pentaoxepane-5,7-dione Chemical compound O=C1OOOOC(=O)O1 BEQKKZICTDFVMG-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- PITQFWWNUHMYIC-UHFFFAOYSA-N 1-tert-butyl-4-(4-tert-butylcyclohexyl)peroxycyclohexane Chemical group C1CC(C(C)(C)C)CCC1OOC1CCC(C(C)(C)C)CC1 PITQFWWNUHMYIC-UHFFFAOYSA-N 0.000 description 1
- IGGDKDTUCAWDAN-UHFFFAOYSA-N 1-vinylnaphthalene Chemical compound C1=CC=C2C(C=C)=CC=CC2=C1 IGGDKDTUCAWDAN-UHFFFAOYSA-N 0.000 description 1
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 1
- FCMUPMSEVHVOSE-UHFFFAOYSA-N 2,3-bis(ethenyl)pyridine Chemical compound C=CC1=CC=CN=C1C=C FCMUPMSEVHVOSE-UHFFFAOYSA-N 0.000 description 1
- WEEMDRWIKYCTQM-UHFFFAOYSA-N 2,6-dimethoxybenzenecarbothioamide Chemical compound COC1=CC=CC(OC)=C1C(N)=S WEEMDRWIKYCTQM-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 1
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical class ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
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- HBJUDHILVBLZJL-UHFFFAOYSA-L [Na+].[Na+].O=C.[O-]S(=O)S([O-])=O Chemical compound [Na+].[Na+].O=C.[O-]S(=O)S([O-])=O HBJUDHILVBLZJL-UHFFFAOYSA-L 0.000 description 1
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- 150000001875 compounds Chemical class 0.000 description 1
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- 239000007771 core particle Substances 0.000 description 1
- 229920006037 cross link polymer Polymers 0.000 description 1
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- 125000000753 cycloalkyl group Chemical group 0.000 description 1
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- ZFTFAPZRGNKQPU-UHFFFAOYSA-N dicarbonic acid Chemical compound OC(=O)OC(O)=O ZFTFAPZRGNKQPU-UHFFFAOYSA-N 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
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- 238000001035 drying Methods 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 238000007720 emulsion polymerization reaction Methods 0.000 description 1
- GFJVXXWOPWLRNU-UHFFFAOYSA-N ethenyl formate Chemical compound C=COC=O GFJVXXWOPWLRNU-UHFFFAOYSA-N 0.000 description 1
- 125000005670 ethenylalkyl group Chemical group 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 229940083124 ganglion-blocking antiadrenergic secondary and tertiary amines Drugs 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 150000002432 hydroperoxides Chemical class 0.000 description 1
- 125000001165 hydrophobic group Chemical group 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
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- 238000010348 incorporation Methods 0.000 description 1
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- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- 230000005865 ionizing radiation Effects 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
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- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 1
- 125000005395 methacrylic acid group Chemical class 0.000 description 1
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- ZIUHHBKFKCYYJD-UHFFFAOYSA-N n,n'-methylenebisacrylamide Chemical compound C=CC(=O)NCNC(=O)C=C ZIUHHBKFKCYYJD-UHFFFAOYSA-N 0.000 description 1
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- UCUUFSAXZMGPGH-UHFFFAOYSA-N penta-1,4-dien-3-one Chemical compound C=CC(=O)C=C UCUUFSAXZMGPGH-UHFFFAOYSA-N 0.000 description 1
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- 238000005191 phase separation Methods 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 125000003884 phenylalkyl group Chemical group 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000012673 precipitation polymerization Methods 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000012966 redox initiator Substances 0.000 description 1
- 238000009938 salting Methods 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
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- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
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- 239000011593 sulfur Substances 0.000 description 1
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- 229960001124 trientine Drugs 0.000 description 1
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Classifications
-
- 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
- C08J9/00—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
- C08J9/16—Making expandable particles
- C08J9/20—Making expandable particles by suspension polymerisation in the presence of the blowing agent
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D15/00—Separating processes involving the treatment of liquids with solid sorbents; Apparatus therefor
- B01D15/08—Selective adsorption, e.g. chromatography
- B01D15/26—Selective adsorption, e.g. chromatography characterised by the separation mechanism
- B01D15/38—Selective adsorption, e.g. chromatography characterised by the separation mechanism involving specific interaction not covered by one or more of groups B01D15/265 and B01D15/30 - B01D15/36, e.g. affinity, ligand exchange or chiral chromatography
- B01D15/3804—Affinity chromatography
- B01D15/3809—Affinity chromatography of the antigen-antibody type, e.g. protein A, G or L chromatography
-
- 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
- B01J20/22—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising organic material
- B01J20/26—Synthetic 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
- B01J43/00—Amphoteric ion-exchange, i.e. using ion-exchangers having cationic and anionic groups; Use of material as amphoteric ion-exchangers; Treatment of material for improving their amphoteric ion-exchange properties
-
- 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
- C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
- C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
- C08F20/08—Anhydrides
-
- 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
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/08—Anhydrides
-
- 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
- C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
- C08F222/10—Esters
- C08F222/1006—Esters of polyhydric alcohols or polyhydric phenols
-
- 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
- C08F8/12—Hydrolysis
-
- 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
-
- 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
- C08F2800/00—Copolymer characterised by the proportions of the comonomers expressed
- C08F2800/20—Copolymer characterised by the proportions of the comonomers expressed as weight or mass percentages
-
- 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
- C08F2810/00—Chemical modification of a polymer
- C08F2810/20—Chemical modification of a polymer leading to a crosslinking, either explicitly or inherently
-
- 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
- C08J2333/00—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Derivatives of such polymers
- C08J2333/02—Homopolymers or copolymers of acids; Metal or ammonium salts thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- General Chemical & Material Sciences (AREA)
- Analytical Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Immunology (AREA)
- Molecular Biology (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Processes Of Treating Macromolecular Substances (AREA)
- Polymerisation Methods In General (AREA)
- Other Resins Obtained By Reactions Not Involving Carbon-To-Carbon Unsaturated Bonds (AREA)
- Polyamides (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US89138192A | 1992-05-29 | 1992-05-29 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| HU9301586D0 HU9301586D0 (en) | 1993-09-28 |
| HUT66373A HUT66373A (en) | 1994-11-28 |
| HU213523B true HU213523B (en) | 1997-07-28 |
Family
ID=25398095
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU9301586A HU213523B (en) | 1992-05-29 | 1993-05-28 | Process for producing crosslinked copolymers predominantly comprising units formed from methacrylic anhydride and process using said copolymers for adsorption, ion exchange or affinity chromatography and adsorbing of proteins |
Country Status (18)
| Country | Link |
|---|---|
| US (2) | US5539071A (enExample) |
| EP (1) | EP0572115B1 (enExample) |
| JP (1) | JP3594629B2 (enExample) |
| KR (1) | KR100286528B1 (enExample) |
| CN (1) | CN1042434C (enExample) |
| AT (1) | ATE163657T1 (enExample) |
| AU (1) | AU3710093A (enExample) |
| BR (1) | BR9302022A (enExample) |
| CA (1) | CA2096492A1 (enExample) |
| CZ (1) | CZ102393A3 (enExample) |
| DE (1) | DE69317154T2 (enExample) |
| HU (1) | HU213523B (enExample) |
| MX (1) | MX9302873A (enExample) |
| NO (1) | NO931883L (enExample) |
| NZ (1) | NZ247458A (enExample) |
| SK (1) | SK52493A3 (enExample) |
| TW (1) | TW222283B (enExample) |
| ZA (1) | ZA933060B (enExample) |
Families Citing this family (34)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6107429A (en) * | 1994-10-24 | 2000-08-22 | Amcol International Corporation | Process for producing an oil and water adsorbent polymer capable of entrapping solid particles and liquids and the product thereof |
| US5837790A (en) | 1994-10-24 | 1998-11-17 | Amcol International Corporation | Precipitation polymerization process for producing an oil adsorbent polymer capable of entrapping solid particles and liquids and the product thereof |
| US5830967A (en) * | 1994-10-24 | 1998-11-03 | Amcol International Corporation | Process for producing an oil and water adsorbent polymer capable of entrapping solid particles and liquids and the product thereof |
| US5712358A (en) * | 1995-06-07 | 1998-01-27 | Amcol International Corporation | Process for producing an oil sorbent copolymer and the product thereof |
| IT1282651B1 (it) * | 1996-02-19 | 1998-03-31 | Atohaas Holding Cv | Processo per la preparazione di perle di polimeri a base acrilica |
| US6228340B1 (en) | 1997-08-25 | 2001-05-08 | The Regents Of The University Of California | Method for the production of macroporous ceramics |
| US6274687B1 (en) * | 1997-09-04 | 2001-08-14 | Daiso Co., Ltd. | Powder of agglomerated fine particles of crosslinked allyl copolymer |
| FR2781232B1 (fr) * | 1998-07-15 | 2000-09-08 | Centre Nat Rech Scient | Polymere reactif utilisable pour la separation et l'adsorption de substances organiques, et materiau le contenant |
| DE19907023A1 (de) * | 1999-02-19 | 2000-08-24 | Bayer Ag | Verfahren zur Isolierung von Nucleinsäuren |
| GB9918437D0 (en) * | 1999-08-05 | 1999-10-06 | Anglo American Platinum Corp | Separation of platinium group metals |
| DE50205698D1 (de) * | 2002-10-22 | 2006-04-13 | Metrohm Ag Herisau | Verfahren zur Herstellung von porösen Polymerteilchen auf Acrylat- und/oder Methacrylatbasis |
| US6752853B2 (en) * | 2002-10-31 | 2004-06-22 | Samsung Electronics Co., Ltd. | Article and method for elimination of hydrocarbon emissions from printer exhaust |
| CN1689695B (zh) * | 2004-04-30 | 2010-06-23 | 北京九强生物技术有限公司 | 层析颗粒介质的制备方法 |
| US8377091B2 (en) | 2006-06-15 | 2013-02-19 | Microvention, Inc. | Embolization device constructed from expansile polymer |
| EP2424775B1 (en) * | 2009-04-30 | 2016-02-10 | Technip France | Spar mooring line sharing method and system |
| KR101898466B1 (ko) | 2011-11-11 | 2018-09-13 | 롬 앤드 하스 캄파니 | 폴리메타크릴산 무수물 텔로머 |
| US9499642B2 (en) * | 2011-11-11 | 2016-11-22 | Rohm And Haas Company | Small particle size hypophosphite telomers of unsaturated carboxylic acids |
| EP2778183B1 (en) | 2013-03-15 | 2015-04-29 | Rohm and Haas Company | Polymethacrylic acid anhydride telomers |
| CN110433326A (zh) | 2014-04-29 | 2019-11-12 | 微仙美国有限公司 | 包含活性剂的聚合物 |
| TW201625754A (zh) * | 2014-11-21 | 2016-07-16 | 艾倫塔斯有限公司 | 單一成份、儲存穩定、可硬化之聚矽氧組成物 |
| WO2016201250A1 (en) * | 2015-06-11 | 2016-12-15 | Microvention, Inc. | Expansile device for implantation |
| AR112849A1 (es) | 2016-11-14 | 2019-12-26 | Lilac Solutions Inc | Extracción de litio con partículas para intercambio iónico recubiertas |
| EP3661619A4 (en) | 2017-08-02 | 2021-05-05 | Lilac Solutions, Inc. | LITHIUM EXTRACTION WITH POROUS ION EXCHANGE BEADS |
| CN111182953A (zh) | 2017-08-02 | 2020-05-19 | 锂莱克解决方案公司 | 用于锂提取的离子交换系统 |
| US11865531B2 (en) | 2018-02-28 | 2024-01-09 | Lilac Solutions, Inc. | Ion exchange reactor with particle traps for lithium extraction |
| US20200055022A1 (en) * | 2018-08-14 | 2020-02-20 | 1441413 Alberta Inc. DBA EPT | Highly porous coolant conditioning and remediation media |
| JP2023514803A (ja) | 2020-01-09 | 2023-04-11 | ライラック ソリューションズ，インク． | 望ましくない金属を分離するための方法 |
| EP4162087A4 (en) | 2020-06-09 | 2024-11-06 | Lilac Solutions, Inc. | LITHIUM EXTRACTION IN THE PRESENCE OF SCALANTS |
| EP4247759A1 (en) | 2020-11-20 | 2023-09-27 | Lilac Solutions, Inc. | Lithium production with volatile acid |
| JP7516243B2 (ja) * | 2020-12-25 | 2024-07-16 | 株式会社カネカ | ポリ（３－ヒドロキシアルカノエート）系発泡粒子およびポリ（３－ヒドロキシアルカノエート）系発泡成形体 |
| JP7646352B2 (ja) * | 2020-12-25 | 2025-03-17 | 株式会社カネカ | ポリ（３－ヒドロキシアルカノエート）系発泡粒子およびポリ（３－ヒドロキシアルカノエート）系発泡成形体 |
| AR125722A1 (es) | 2021-04-23 | 2023-08-09 | Lilac Solutions Inc | Dispositivos de intercambio iónico para la extracción de litio |
| CA3245668A1 (en) | 2022-03-28 | 2023-10-05 | Lilac Solutions Inc | DEVICES FOR THE EFFICIENT USE OF SORBANTS IN LITHIUM EXTRACTION |
| WO2023192623A2 (en) | 2022-04-01 | 2023-10-05 | Lilac Solutions, Inc. | Extraction of lithium with chemical additives |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2324935A (en) * | 1938-05-20 | 1943-07-20 | Rohm & Haas | Process for polymerizing derivatives of methacrylic acid |
| US2308581A (en) * | 1939-05-05 | 1943-01-19 | Du Pont | Copolymerized substances containing methacrylic anhydride |
| GB781400A (en) * | 1954-09-13 | 1957-08-21 | Roehm & Haas Gmbh | Improvements in or relating to ion-exchange resins |
| NL98224C (enExample) * | 1955-12-27 | |||
| SE328716B (enExample) * | 1961-12-15 | 1970-09-21 | Rio Rad Lab | |
| FR1603393A (enExample) * | 1967-12-27 | 1971-04-13 | ||
| US4221871A (en) * | 1970-12-16 | 1980-09-09 | Rohm And Haas Company | Reticular crosslinked monovinylidene N-heterocyclic copolymer |
| DE2215687C3 (de) * | 1972-03-30 | 1980-12-11 | Bayer Ag, 5090 Leverkusen | Neue wasserunlösliche Proteinpräparate |
| US4070348A (en) * | 1973-07-25 | 1978-01-24 | Rohm Gmbh | Water-swellable, bead copolymer |
| US4229547A (en) * | 1979-03-19 | 1980-10-21 | The B. F. Goodrich Company | Method of preparing spherical porous bead-type polymers |
| JPS59225064A (ja) * | 1983-06-03 | 1984-12-18 | ユニチカ株式会社 | 生理活性物質固定化用担体 |
| PT80975B (pt) * | 1984-08-17 | 1987-11-11 | Shinetsu Chemical Co | Processo para a preparacao de um polimero de vinilo |
-
1993
- 1993-04-21 DE DE69317154T patent/DE69317154T2/de not_active Expired - Lifetime
- 1993-04-21 EP EP93303125A patent/EP0572115B1/en not_active Expired - Lifetime
- 1993-04-21 AT AT93303125T patent/ATE163657T1/de not_active IP Right Cessation
- 1993-04-21 NZ NZ247458A patent/NZ247458A/en unknown
- 1993-04-23 AU AU37100/93A patent/AU3710093A/en not_active Abandoned
- 1993-04-23 TW TW082103119A patent/TW222283B/zh active
- 1993-04-30 ZA ZA933060A patent/ZA933060B/xx unknown
- 1993-05-18 CA CA002096492A patent/CA2096492A1/en not_active Abandoned
- 1993-05-18 MX MX9302873A patent/MX9302873A/es not_active IP Right Cessation
- 1993-05-20 BR BR9302022A patent/BR9302022A/pt not_active Application Discontinuation
- 1993-05-24 SK SK524-93A patent/SK52493A3/sk unknown
- 1993-05-25 NO NO931883A patent/NO931883L/no unknown
- 1993-05-27 KR KR1019930009366A patent/KR100286528B1/ko not_active Expired - Fee Related
- 1993-05-28 CZ CZ931023A patent/CZ102393A3/cs unknown
- 1993-05-28 CN CN93106493A patent/CN1042434C/zh not_active Expired - Fee Related
- 1993-05-28 JP JP12733293A patent/JP3594629B2/ja not_active Expired - Fee Related
- 1993-05-28 HU HU9301586A patent/HU213523B/hu not_active IP Right Cessation
-
1995
- 1995-06-06 US US08/467,674 patent/US5539071A/en not_active Expired - Lifetime
- 1995-06-06 US US08/467,675 patent/US5639861A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| ATE163657T1 (de) | 1998-03-15 |
| US5639861A (en) | 1997-06-17 |
| NO931883L (no) | 1993-11-30 |
| DE69317154D1 (de) | 1998-04-09 |
| TW222283B (enExample) | 1994-04-11 |
| EP0572115A2 (en) | 1993-12-01 |
| CN1079229A (zh) | 1993-12-08 |
| HU9301586D0 (en) | 1993-09-28 |
| BR9302022A (pt) | 1993-12-07 |
| DE69317154T2 (de) | 1998-11-12 |
| EP0572115A3 (enExample) | 1994-03-16 |
| CZ102393A3 (en) | 1993-12-15 |
| ZA933060B (en) | 1993-11-29 |
| EP0572115B1 (en) | 1998-03-04 |
| CN1042434C (zh) | 1999-03-10 |
| US5539071A (en) | 1996-07-23 |
| KR100286528B1 (ko) | 2001-04-16 |
| SK52493A3 (en) | 1993-12-08 |
| MX9302873A (es) | 1993-11-01 |
| HUT66373A (en) | 1994-11-28 |
| AU3710093A (en) | 1993-12-02 |
| NO931883D0 (no) | 1993-05-25 |
| NZ247458A (en) | 1994-09-27 |
| KR930023390A (ko) | 1993-12-18 |
| JPH0649139A (ja) | 1994-02-22 |
| CA2096492A1 (en) | 1993-11-30 |
| JP3594629B2 (ja) | 2004-12-02 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| HMM4 | Cancellation of final prot. due to non-payment of fee |