DE102007060790A1 - Verfahren zur Herstellung von Kationenaustauschern - Google Patents
Verfahren zur Herstellung von Kationenaustauschern Download PDFInfo
- Publication number
- DE102007060790A1 DE102007060790A1 DE102007060790A DE102007060790A DE102007060790A1 DE 102007060790 A1 DE102007060790 A1 DE 102007060790A1 DE 102007060790 A DE102007060790 A DE 102007060790A DE 102007060790 A DE102007060790 A DE 102007060790A DE 102007060790 A1 DE102007060790 A1 DE 102007060790A1
- Authority
- DE
- Germany
- Prior art keywords
- vinyl
- cation exchanger
- water
- bead polymers
- cation exchangers
- 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.)
- Withdrawn
Links
- 150000001768 cations Chemical class 0.000 title claims description 66
- 238000002360 preparation method Methods 0.000 title claims description 29
- 238000000034 method Methods 0.000 title claims description 18
- 229920000642 polymer Polymers 0.000 claims abstract description 75
- 239000011324 bead Substances 0.000 claims abstract description 69
- 239000000178 monomer Substances 0.000 claims abstract description 24
- 238000006277 sulfonation reaction Methods 0.000 claims abstract description 18
- 239000004971 Cross linker Substances 0.000 claims abstract description 17
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 claims abstract description 15
- 229920001567 vinyl ester resin Polymers 0.000 claims abstract description 15
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 54
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 42
- 239000002245 particle Substances 0.000 claims description 17
- 239000002253 acid Substances 0.000 claims description 15
- 230000002378 acidificating effect Effects 0.000 claims description 15
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 11
- 229920002554 vinyl polymer Polymers 0.000 claims description 9
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 7
- 238000009826 distribution Methods 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 229910021642 ultra pure water Inorganic materials 0.000 claims description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 claims description 4
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 claims description 4
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 claims description 3
- 239000003054 catalyst Substances 0.000 claims description 3
- 229930091371 Fructose Natural products 0.000 claims description 2
- 239000005715 Fructose Substances 0.000 claims description 2
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 claims description 2
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 2
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 claims description 2
- 238000013375 chromatographic separation Methods 0.000 claims description 2
- 239000003651 drinking water Substances 0.000 claims description 2
- 235000020188 drinking water Nutrition 0.000 claims description 2
- 239000008103 glucose Substances 0.000 claims description 2
- 238000010557 suspension polymerization reaction Methods 0.000 claims description 2
- 239000012498 ultrapure water Substances 0.000 claims description 2
- 230000003647 oxidation Effects 0.000 abstract description 20
- 238000007254 oxidation reaction Methods 0.000 abstract description 20
- 230000003204 osmotic effect Effects 0.000 abstract description 11
- 125000002091 cationic group Chemical group 0.000 abstract 1
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 28
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 26
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 24
- 229920005989 resin Polymers 0.000 description 22
- 239000011347 resin Substances 0.000 description 22
- 239000000203 mixture Substances 0.000 description 21
- 239000000243 solution Substances 0.000 description 16
- 239000008367 deionised water Substances 0.000 description 11
- 238000006116 polymerization reaction Methods 0.000 description 11
- 229910021641 deionized water Inorganic materials 0.000 description 10
- SAMJGBVVQUEMGC-UHFFFAOYSA-N 1-ethenoxy-2-(2-ethenoxyethoxy)ethane Chemical compound C=COCCOCCOC=C SAMJGBVVQUEMGC-UHFFFAOYSA-N 0.000 description 9
- 239000003361 porogen Substances 0.000 description 9
- 235000011121 sodium hydroxide Nutrition 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
- 239000008346 aqueous phase Substances 0.000 description 8
- 238000001816 cooling Methods 0.000 description 8
- 239000003999 initiator Substances 0.000 description 8
- 230000008961 swelling Effects 0.000 description 8
- 229920001479 Hydroxyethyl methyl cellulose Polymers 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 7
- 239000011521 glass Substances 0.000 description 7
- 239000003112 inhibitor Substances 0.000 description 7
- 239000012074 organic phase Substances 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- ZXHDVRATSGZISC-UHFFFAOYSA-N 1,2-bis(ethenoxy)ethane Chemical compound C=COCCOC=C ZXHDVRATSGZISC-UHFFFAOYSA-N 0.000 description 5
- 238000013459 approach Methods 0.000 description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- -1 isopropenyl alcohol Chemical compound 0.000 description 5
- 229910052760 oxygen Inorganic materials 0.000 description 5
- 239000001301 oxygen Substances 0.000 description 5
- WYKYCHHWIJXDAO-UHFFFAOYSA-N tert-butyl 2-ethylhexaneperoxoate Chemical compound CCCCC(CC)C(=O)OOC(C)(C)C WYKYCHHWIJXDAO-UHFFFAOYSA-N 0.000 description 5
- 229960000834 vinyl ether Drugs 0.000 description 5
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 4
- 108010010803 Gelatin Proteins 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 4
- 235000019400 benzoyl peroxide Nutrition 0.000 description 4
- MPMBRWOOISTHJV-UHFFFAOYSA-N but-1-enylbenzene Chemical compound CCC=CC1=CC=CC=C1 MPMBRWOOISTHJV-UHFFFAOYSA-N 0.000 description 4
- 229920001577 copolymer Polymers 0.000 description 4
- DGLRDKLJZLEJCY-UHFFFAOYSA-L disodium hydrogenphosphate dodecahydrate Chemical compound O.O.O.O.O.O.O.O.O.O.O.O.[Na+].[Na+].OP([O-])([O-])=O DGLRDKLJZLEJCY-UHFFFAOYSA-L 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 229940052303 ethers for general anesthesia Drugs 0.000 description 4
- 239000012634 fragment Substances 0.000 description 4
- 229920000159 gelatin Polymers 0.000 description 4
- 239000008273 gelatin Substances 0.000 description 4
- 235000019322 gelatine Nutrition 0.000 description 4
- 235000011852 gelatine desserts Nutrition 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- MWZJGRDWJVHRDV-UHFFFAOYSA-N 1,4-bis(ethenoxy)butane Chemical compound C=COCCCCOC=C MWZJGRDWJVHRDV-UHFFFAOYSA-N 0.000 description 3
- VUIWJRYTWUGOOF-UHFFFAOYSA-N 2-ethenoxyethanol Chemical compound OCCOC=C VUIWJRYTWUGOOF-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- IMROMDMJAWUWLK-UHFFFAOYSA-N Ethenol Chemical compound OC=C IMROMDMJAWUWLK-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
- 239000003963 antioxidant agent Substances 0.000 description 3
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 3
- 239000004327 boric acid Substances 0.000 description 3
- 230000003247 decreasing effect Effects 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 238000010348 incorporation Methods 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 239000011049 pearl Substances 0.000 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 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
- GTJOHISYCKPIMT-UHFFFAOYSA-N 2-methylundecane Chemical compound CCCCCCCCCC(C)C GTJOHISYCKPIMT-UHFFFAOYSA-N 0.000 description 2
- WVYWICLMDOOCFB-UHFFFAOYSA-N 4-methyl-2-pentanol Chemical compound CC(C)CC(C)O WVYWICLMDOOCFB-UHFFFAOYSA-N 0.000 description 2
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- SGVYKUFIHHTIFL-UHFFFAOYSA-N Isobutylhexyl Natural products CCCCCCCC(C)C SGVYKUFIHHTIFL-UHFFFAOYSA-N 0.000 description 2
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 2
- HETCEOQFVDFGSY-UHFFFAOYSA-N Isopropenyl acetate Chemical compound CC(=C)OC(C)=O HETCEOQFVDFGSY-UHFFFAOYSA-N 0.000 description 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 206010041662 Splinter Diseases 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 150000001491 aromatic compounds Chemical class 0.000 description 2
- 238000000889 atomisation Methods 0.000 description 2
- KBPLFHHGFOOTCA-UHFFFAOYSA-N caprylic alcohol Natural products CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- 238000005341 cation exchange Methods 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- 230000007547 defect Effects 0.000 description 2
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 description 2
- VKPSKYDESGTTFR-UHFFFAOYSA-N isododecane Natural products CC(C)(C)CC(C)CC(C)(C)C VKPSKYDESGTTFR-UHFFFAOYSA-N 0.000 description 2
- 238000002386 leaching Methods 0.000 description 2
- QYZFTMMPKCOTAN-UHFFFAOYSA-N n-[2-(2-hydroxyethylamino)ethyl]-2-[[1-[2-(2-hydroxyethylamino)ethylamino]-2-methyl-1-oxopropan-2-yl]diazenyl]-2-methylpropanamide Chemical compound OCCNCCNC(=O)C(C)(C)N=NC(C)(C)C(=O)NCCNCCO QYZFTMMPKCOTAN-UHFFFAOYSA-N 0.000 description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- 229920000172 poly(styrenesulfonic acid) Polymers 0.000 description 2
- 239000011148 porous material Substances 0.000 description 2
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 2
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- CHQMHPLRPQMAMX-UHFFFAOYSA-L sodium persulfate Chemical compound [Na+].[Na+].[O-]S(=O)(=O)OOS([O-])(=O)=O CHQMHPLRPQMAMX-UHFFFAOYSA-L 0.000 description 2
- 238000013112 stability test Methods 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000000542 sulfonic acid group Chemical group 0.000 description 2
- 230000000007 visual effect Effects 0.000 description 2
- HGXJDMCMYLEZMJ-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy 2,2-dimethylpropaneperoxoate Chemical compound CC(C)(C)OOOC(=O)C(C)(C)C HGXJDMCMYLEZMJ-UHFFFAOYSA-N 0.000 description 1
- BUHVIAUBTBOHAG-FOYDDCNASA-N (2r,3r,4s,5r)-2-[6-[[2-(3,5-dimethoxyphenyl)-2-(2-methylphenyl)ethyl]amino]purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol Chemical compound COC1=CC(OC)=CC(C(CNC=2C=3N=CN(C=3N=CN=2)[C@H]2[C@@H]([C@H](O)[C@@H](CO)O2)O)C=2C(=CC=CC=2)C)=C1 BUHVIAUBTBOHAG-FOYDDCNASA-N 0.000 description 1
- OXYKVVLTXXXVRT-UHFFFAOYSA-N (4-chlorobenzoyl) 4-chlorobenzenecarboperoxoate Chemical compound C1=CC(Cl)=CC=C1C(=O)OOC(=O)C1=CC=C(Cl)C=C1 OXYKVVLTXXXVRT-UHFFFAOYSA-N 0.000 description 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- KNKRKFALVUDBJE-UHFFFAOYSA-N 1,2-dichloropropane Chemical compound CC(Cl)CCl KNKRKFALVUDBJE-UHFFFAOYSA-N 0.000 description 1
- QTYUSOHYEPOHLV-FNORWQNLSA-N 1,3-Octadiene Chemical compound CCCC\C=C\C=C QTYUSOHYEPOHLV-FNORWQNLSA-N 0.000 description 1
- LGJCFVYMIJLQJO-UHFFFAOYSA-N 1-dodecylperoxydodecane Chemical compound CCCCCCCCCCCCOOCCCCCCCCCCCC LGJCFVYMIJLQJO-UHFFFAOYSA-N 0.000 description 1
- FPSURBCYSCOZSE-UHFFFAOYSA-N 1-ethenoxybutan-1-ol Chemical compound CCCC(O)OC=C FPSURBCYSCOZSE-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
- MDPFMNDCSZZZIZ-UHFFFAOYSA-N 2,2,4,4,7,7,9,9-octamethyldecane-3,8-dione Chemical compound CC(C)(C)C(=O)C(C)(C)CCC(C)(C)C(=O)C(C)(C)C MDPFMNDCSZZZIZ-UHFFFAOYSA-N 0.000 description 1
- BJELTSYBAHKXRW-UHFFFAOYSA-N 2,4,6-triallyloxy-1,3,5-triazine Chemical compound C=CCOC1=NC(OCC=C)=NC(OCC=C)=N1 BJELTSYBAHKXRW-UHFFFAOYSA-N 0.000 description 1
- OHVNEQDNPSQOOT-UHFFFAOYSA-N 2,5-dimethylhexan-2-yl 7,7-dimethyloctaneperoxoate Chemical compound CC(C)CCC(C)(C)OOC(=O)CCCCCC(C)(C)C OHVNEQDNPSQOOT-UHFFFAOYSA-N 0.000 description 1
- 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 1
- WULAHPYSGCVQHM-UHFFFAOYSA-N 2-(2-ethenoxyethoxy)ethanol Chemical compound OCCOCCOC=C WULAHPYSGCVQHM-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
- QMYCJCOPYOPWTI-UHFFFAOYSA-N 2-[(1-amino-1-imino-2-methylpropan-2-yl)diazenyl]-2-methylpropanimidamide;hydron;chloride Chemical compound Cl.NC(=N)C(C)(C)N=NC(C)(C)C(N)=N QMYCJCOPYOPWTI-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
- FSGHEPDRMHVUCQ-UHFFFAOYSA-N 2-ethoxyprop-1-ene Chemical compound CCOC(C)=C FSGHEPDRMHVUCQ-UHFFFAOYSA-N 0.000 description 1
- YOWQWFMSQCOSBA-UHFFFAOYSA-N 2-methoxypropene Chemical compound COC(C)=C YOWQWFMSQCOSBA-UHFFFAOYSA-N 0.000 description 1
- RAWISQFSQWIXCW-UHFFFAOYSA-N 2-methylbutan-2-yl 2,2-dimethyloctaneperoxoate Chemical compound CCCCCCC(C)(C)C(=O)OOC(C)(C)CC RAWISQFSQWIXCW-UHFFFAOYSA-N 0.000 description 1
- AQKYLAIZOGOPAW-UHFFFAOYSA-N 2-methylbutan-2-yl 2,2-dimethylpropaneperoxoate Chemical compound CCC(C)(C)OOC(=O)C(C)(C)C AQKYLAIZOGOPAW-UHFFFAOYSA-N 0.000 description 1
- IFXDUNDBQDXPQZ-UHFFFAOYSA-N 2-methylbutan-2-yl 2-ethylhexaneperoxoate Chemical compound CCCCC(CC)C(=O)OOC(C)(C)CC IFXDUNDBQDXPQZ-UHFFFAOYSA-N 0.000 description 1
- DXIJHCSGLOHNES-UHFFFAOYSA-N 3,3-dimethylbut-1-enylbenzene Chemical compound CC(C)(C)C=CC1=CC=CC=C1 DXIJHCSGLOHNES-UHFFFAOYSA-N 0.000 description 1
- XYFRHHAYSXIKGH-UHFFFAOYSA-N 3-(5-methoxy-2-methoxycarbonyl-1h-indol-3-yl)prop-2-enoic acid Chemical compound C1=C(OC)C=C2C(C=CC(O)=O)=C(C(=O)OC)NC2=C1 XYFRHHAYSXIKGH-UHFFFAOYSA-N 0.000 description 1
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- IWTYTFSSTWXZFU-UHFFFAOYSA-N 3-chloroprop-1-enylbenzene Chemical compound ClCC=CC1=CC=CC=C1 IWTYTFSSTWXZFU-UHFFFAOYSA-N 0.000 description 1
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- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 1
- 239000012935 ammoniumperoxodisulfate Substances 0.000 description 1
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- PIPBVABVQJZSAB-UHFFFAOYSA-N bis(ethenyl) benzene-1,2-dicarboxylate Chemical compound C=COC(=O)C1=CC=CC=C1C(=O)OC=C PIPBVABVQJZSAB-UHFFFAOYSA-N 0.000 description 1
- 150000001642 boronic acid derivatives Chemical class 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 239000007853 buffer solution Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
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- 229920003086 cellulose ether Polymers 0.000 description 1
- ZCDOYSPFYFSLEW-UHFFFAOYSA-N chromate(2-) Chemical class [O-][Cr]([O-])(=O)=O ZCDOYSPFYFSLEW-UHFFFAOYSA-N 0.000 description 1
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- BLCKNMAZFRMCJJ-UHFFFAOYSA-N cyclohexyl cyclohexyloxycarbonyloxy carbonate Chemical compound C1CCCCC1OC(=O)OOC(=O)OC1CCCCC1 BLCKNMAZFRMCJJ-UHFFFAOYSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 239000007857 degradation product Substances 0.000 description 1
- FVCOIAYSJZGECG-UHFFFAOYSA-N diethylhydroxylamine Chemical compound CCN(O)CC FVCOIAYSJZGECG-UHFFFAOYSA-N 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000012674 dispersion polymerization Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000003628 erosive effect Effects 0.000 description 1
- LPUZTLKYAOOFDX-QXMHVHEDSA-N ethenyl (z)-octadec-9-enoate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC=C LPUZTLKYAOOFDX-QXMHVHEDSA-N 0.000 description 1
- MEGHWIAOTJPCHQ-UHFFFAOYSA-N ethenyl butanoate Chemical compound CCCC(=O)OC=C MEGHWIAOTJPCHQ-UHFFFAOYSA-N 0.000 description 1
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- GFJVXXWOPWLRNU-UHFFFAOYSA-N ethenyl formate Chemical compound C=COC=O GFJVXXWOPWLRNU-UHFFFAOYSA-N 0.000 description 1
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- 238000011156 evaluation Methods 0.000 description 1
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- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
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- 229920000609 methyl cellulose Polymers 0.000 description 1
- XJRBAMWJDBPFIM-UHFFFAOYSA-N methyl vinyl ether Chemical compound COC=C XJRBAMWJDBPFIM-UHFFFAOYSA-N 0.000 description 1
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- 229910017464 nitrogen compound Inorganic materials 0.000 description 1
- 150000002830 nitrogen compounds Chemical class 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 1
- DBSDMAPJGHBWAL-UHFFFAOYSA-N penta-1,4-dien-3-ylbenzene Chemical compound C=CC(C=C)C1=CC=CC=C1 DBSDMAPJGHBWAL-UHFFFAOYSA-N 0.000 description 1
- 125000005385 peroxodisulfate group Chemical group 0.000 description 1
- 125000000864 peroxy group Chemical group O(O*)* 0.000 description 1
- JAMNHZBIQDNHMM-UHFFFAOYSA-N pivalonitrile Chemical compound CC(C)(C)C#N JAMNHZBIQDNHMM-UHFFFAOYSA-N 0.000 description 1
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- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
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- 235000010289 potassium nitrite Nutrition 0.000 description 1
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- 235000010288 sodium nitrite Nutrition 0.000 description 1
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- 235000011152 sodium sulphate Nutrition 0.000 description 1
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- 239000008107 starch Substances 0.000 description 1
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- 239000001117 sulphuric acid Substances 0.000 description 1
- PFBLRDXPNUJYJM-UHFFFAOYSA-N tert-butyl 2-methylpropaneperoxoate Chemical compound CC(C)C(=O)OOC(C)(C)C PFBLRDXPNUJYJM-UHFFFAOYSA-N 0.000 description 1
- NMOALOSNPWTWRH-UHFFFAOYSA-N tert-butyl 7,7-dimethyloctaneperoxoate Chemical compound CC(C)(C)CCCCCC(=O)OOC(C)(C)C NMOALOSNPWTWRH-UHFFFAOYSA-N 0.000 description 1
- VEQHTYHLJYNSTG-UHFFFAOYSA-N tert-butyl 9-tert-butylperoxy-9-oxononanoate Chemical compound CC(C)(C)OOC(=O)CCCCCCCC(=O)OC(C)(C)C VEQHTYHLJYNSTG-UHFFFAOYSA-N 0.000 description 1
- BWSZXUOMATYHHI-UHFFFAOYSA-N tert-butyl octaneperoxoate Chemical compound CCCCCCCC(=O)OOC(C)(C)C BWSZXUOMATYHHI-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- 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
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/06—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing polymers
- B01J31/08—Ion-exchange resins
- B01J31/10—Ion-exchange resins sulfonated
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/11—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms
- C07C37/20—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms using aldehydes or ketones
-
- 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
- C08F8/34—Introducing sulfur atoms or sulfur-containing groups
- C08F8/36—Sulfonation; Sulfation
-
- C—CHEMISTRY; METALLURGY
- C13—SUGAR INDUSTRY
- C13B—PRODUCTION OF SUCROSE; APPARATUS SPECIALLY ADAPTED THEREFOR
- C13B20/00—Purification of sugar juices
- C13B20/14—Purification of sugar juices using ion-exchange materials
- C13B20/148—Purification of sugar juices using ion-exchange materials for fractionating, adsorption or ion exclusion processes combined with elution or desorption of a sugar fraction
-
- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F1/00—Treatment of water, waste water, or sewage
- C02F1/42—Treatment of water, waste water, or sewage by ion-exchange
- C02F2001/425—Treatment of water, waste water, or sewage by ion-exchange using cation exchangers
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Analytical Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Manufacture Of Macromolecular Shaped Articles (AREA)
- Treatment Of Water By Ion Exchange (AREA)
Priority Applications (10)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102007060790A DE102007060790A1 (de) | 2007-12-18 | 2007-12-18 | Verfahren zur Herstellung von Kationenaustauschern |
| EP11155485A EP2340889A1 (de) | 2007-12-18 | 2008-12-04 | Verfahren zur Herstellung von Kationenaustauschern |
| EP08170635.0A EP2077158B1 (de) | 2007-12-18 | 2008-12-04 | Starksaure kationenaustauscher, verfahren zur herstellung solcher kationenaustauscher sowie verwendungen davon |
| US12/334,570 US20090156798A1 (en) | 2007-12-18 | 2008-12-15 | Process for producing cation exchangers |
| UAA200814560A UA102810C2 (ru) | 2007-12-18 | 2008-12-17 | Сильнокислое катионообменное вещество и способ его получения |
| JP2008321361A JP5714207B2 (ja) | 2007-12-18 | 2008-12-17 | 陽イオン交換体の製造方法 |
| RU2008149767/05A RU2494812C2 (ru) | 2007-12-18 | 2008-12-17 | Сильнокислый катионообменник, способ его производства и применение |
| CN2008101835898A CN101462083B (zh) | 2007-12-18 | 2008-12-18 | 生产阳离子交换剂的方法 |
| US13/268,122 US8207284B2 (en) | 2007-12-18 | 2011-10-07 | Process for producing cation exchangers |
| US13/482,272 US8362182B2 (en) | 2007-12-18 | 2012-05-29 | Process for producing cation exchangers |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102007060790A DE102007060790A1 (de) | 2007-12-18 | 2007-12-18 | Verfahren zur Herstellung von Kationenaustauschern |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE102007060790A1 true DE102007060790A1 (de) | 2009-06-25 |
Family
ID=40491006
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE102007060790A Withdrawn DE102007060790A1 (de) | 2007-12-18 | 2007-12-18 | Verfahren zur Herstellung von Kationenaustauschern |
Country Status (7)
| Country | Link |
|---|---|
| US (3) | US20090156798A1 (https=) |
| EP (2) | EP2340889A1 (https=) |
| JP (1) | JP5714207B2 (https=) |
| CN (1) | CN101462083B (https=) |
| DE (1) | DE102007060790A1 (https=) |
| RU (1) | RU2494812C2 (https=) |
| UA (1) | UA102810C2 (https=) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BR112014014291A2 (pt) * | 2011-12-28 | 2017-06-13 | Dow Global Technologies Llc | processo para preparar um catalisador |
| TWI494296B (zh) * | 2011-12-28 | 2015-08-01 | Rohm & Haas | 經處理、促進之離子交換樹脂觸媒之用途 |
| CA2859445C (en) * | 2011-12-28 | 2020-06-02 | Rohm And Haas Company | Strong acid catalyst composition |
| US20150353660A1 (en) * | 2014-06-05 | 2015-12-10 | Lanxess Deutschland Gmbh | Process for preparing catalysts |
| CN104496064B (zh) * | 2014-11-21 | 2016-08-24 | 广东源盛生态环保科技有限公司 | 一种利用水压控制垃圾渗滤液定向收集的方法 |
| CN105949355B (zh) * | 2016-07-06 | 2018-01-19 | 凯瑞环保科技股份有限公司 | 一种用于阳离子交换树脂生产的工艺装置及方法 |
| US10481928B2 (en) * | 2016-12-14 | 2019-11-19 | International Business Machines Corporation | Providing user interface language options |
| CN109663618B (zh) * | 2018-12-27 | 2021-10-26 | 无锡市中舶远航环保科技有限公司 | 一种高效的污水处理用离子交换树脂的制备方法 |
| CN111111791A (zh) * | 2020-01-06 | 2020-05-08 | 凯瑞环保科技股份有限公司 | 一种甲基磺酸型阳离子交换树脂及其制备方法 |
Citations (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0046535A2 (de) | 1980-08-22 | 1982-03-03 | Bayer Ag | Verfahren zur Herstellung von Perlpolymerisaten einheitlicher Teilchengrösse |
| DE3230559A1 (de) | 1981-08-21 | 1983-03-03 | Mitsubishi Chemical Industries, Ltd., Tokyo | Verfahren zur herstellung von kationenaustauschharzen |
| EP0101943A2 (en) | 1982-08-02 | 1984-03-07 | The Dow Chemical Company | Ion exchange resins |
| US4500652A (en) | 1981-08-21 | 1985-02-19 | Mitsubishi Chemical Industries, Limited | Process for producing cation exchange resins without swelling during sulphonation process |
| EP0366258A1 (en) | 1988-09-23 | 1990-05-02 | The Dow Chemical Company | Process for preparing cation exchange resins having improved stability and cation exchange resins prepared therefrom |
| EP0617714A1 (en) | 1991-12-19 | 1994-10-05 | Dow Chemical Co | POROES VACCINATED COPOLYMERS AND ION EXCHANGE RESINS MADE THEREOF. |
| EP0868444B1 (de) | 1995-12-21 | 1999-09-22 | IAB Ionenaustauscher GmbH Bitterfeld | Verfahren zur herstellung stark saurer kationenaustauscher |
| EP1000659A1 (de) | 1998-11-16 | 2000-05-17 | Bayer Aktiengesellschaft | Verfahren zur Herstellung von monodispersen gelförmigen Kationenaustauschern |
| DE10122896A1 (de) | 2001-05-11 | 2002-11-14 | Bayer Ag | Verfahren zur Herstellung von monodispersen gelförmigen Kationenaustauschern |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL6905520A (https=) * | 1969-04-10 | 1970-10-13 | ||
| US4419245A (en) * | 1982-06-30 | 1983-12-06 | Rohm And Haas Company | Copolymer process and product therefrom consisting of crosslinked seed bead swollen by styrene monomer |
| US5281631A (en) * | 1991-12-20 | 1994-01-25 | Arch Development Corp. | Phosphonic acid based ion exchange resins |
| JPH0881513A (ja) * | 1994-09-13 | 1996-03-26 | Mitsubishi Chem Corp | 球状架橋重合体の製造方法 |
| DE19644227A1 (de) * | 1996-10-24 | 1998-04-30 | Bayer Ag | Verfahren zur Herstellung ausblutarmer Kationenaustauscher |
| US5804606A (en) * | 1997-04-21 | 1998-09-08 | Rohm & Haas Company | Chelating resins |
| DE10105103A1 (de) * | 2001-02-05 | 2002-08-08 | Bayer Ag | Verfahren zur Herstellung von gelförmigen Kationenaustauschern |
| DE10121163A1 (de) * | 2001-04-30 | 2002-10-31 | Bayer Ag | Verfahren zur Herstellung heterodisperser Chelatharze |
| US6784213B2 (en) * | 2001-06-22 | 2004-08-31 | Rohm And Haas Company | Method for preparation of strong acid cation exchange resins |
| US6750259B2 (en) * | 2002-07-08 | 2004-06-15 | Bayer Aktiengesellschaft | Process for preparing gel-type cation exchangers |
| DE10237601A1 (de) * | 2002-08-16 | 2004-02-26 | Bayer Ag | Verfahren zur Herstellung von monodispersen gelförmigen Ionenaustauschern |
| DE102004006116A1 (de) * | 2004-02-06 | 2005-08-25 | Bayer Chemicals Ag | Verfahren zur Herstellung von monodispersen porenhaltigen Ionenaustauschern |
| DE102005035616A1 (de) * | 2005-07-29 | 2007-02-08 | Lanxess Deutschland Gmbh | Monodisperse Kationenaustauscher |
| RU2283062C1 (ru) * | 2005-09-28 | 2006-09-10 | Меликсет Литвинович Меликян | Способ реставрации бокового зуба при полном отсутствии коронковой части с перфорацией вертикально перемещенного корня в области бифуркации или трифуркации и с разрушением межкорневой перегородки |
| DE102006020874A1 (de) * | 2006-05-05 | 2007-11-08 | Lanxess Deutschland Gmbh | Verfahren zum Entfernen von Lösungsmitteln aus Perlpolymerisaten |
-
2007
- 2007-12-18 DE DE102007060790A patent/DE102007060790A1/de not_active Withdrawn
-
2008
- 2008-12-04 EP EP11155485A patent/EP2340889A1/de not_active Withdrawn
- 2008-12-04 EP EP08170635.0A patent/EP2077158B1/de active Active
- 2008-12-15 US US12/334,570 patent/US20090156798A1/en not_active Abandoned
- 2008-12-17 RU RU2008149767/05A patent/RU2494812C2/ru active
- 2008-12-17 JP JP2008321361A patent/JP5714207B2/ja active Active
- 2008-12-17 UA UAA200814560A patent/UA102810C2/ru unknown
- 2008-12-18 CN CN2008101835898A patent/CN101462083B/zh active Active
-
2011
- 2011-10-07 US US13/268,122 patent/US8207284B2/en active Active
-
2012
- 2012-05-29 US US13/482,272 patent/US8362182B2/en active Active
Patent Citations (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0046535A2 (de) | 1980-08-22 | 1982-03-03 | Bayer Ag | Verfahren zur Herstellung von Perlpolymerisaten einheitlicher Teilchengrösse |
| DE3230559A1 (de) | 1981-08-21 | 1983-03-03 | Mitsubishi Chemical Industries, Ltd., Tokyo | Verfahren zur herstellung von kationenaustauschharzen |
| US4500652A (en) | 1981-08-21 | 1985-02-19 | Mitsubishi Chemical Industries, Limited | Process for producing cation exchange resins without swelling during sulphonation process |
| EP0101943A2 (en) | 1982-08-02 | 1984-03-07 | The Dow Chemical Company | Ion exchange resins |
| EP0366258A1 (en) | 1988-09-23 | 1990-05-02 | The Dow Chemical Company | Process for preparing cation exchange resins having improved stability and cation exchange resins prepared therefrom |
| EP0617714A1 (en) | 1991-12-19 | 1994-10-05 | Dow Chemical Co | POROES VACCINATED COPOLYMERS AND ION EXCHANGE RESINS MADE THEREOF. |
| EP0868444B1 (de) | 1995-12-21 | 1999-09-22 | IAB Ionenaustauscher GmbH Bitterfeld | Verfahren zur herstellung stark saurer kationenaustauscher |
| EP1000659A1 (de) | 1998-11-16 | 2000-05-17 | Bayer Aktiengesellschaft | Verfahren zur Herstellung von monodispersen gelförmigen Kationenaustauschern |
| DE10122896A1 (de) | 2001-05-11 | 2002-11-14 | Bayer Ag | Verfahren zur Herstellung von monodispersen gelförmigen Kationenaustauschern |
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| Title |
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| http://www.gatewayequipment.com/whitepapers/resistivity_instru_futureUPWsystems.pdf |
Also Published As
| Publication number | Publication date |
|---|---|
| RU2494812C2 (ru) | 2013-10-10 |
| US8207284B2 (en) | 2012-06-26 |
| EP2077158A3 (de) | 2010-12-08 |
| UA102810C2 (ru) | 2013-08-27 |
| US8362182B2 (en) | 2013-01-29 |
| EP2077158B1 (de) | 2017-05-31 |
| RU2008149767A (ru) | 2010-06-27 |
| JP5714207B2 (ja) | 2015-05-07 |
| JP2009149887A (ja) | 2009-07-09 |
| CN101462083B (zh) | 2013-04-10 |
| US20120238649A1 (en) | 2012-09-20 |
| CN101462083A (zh) | 2009-06-24 |
| US20120029100A1 (en) | 2012-02-02 |
| EP2340889A1 (de) | 2011-07-06 |
| EP2077158A2 (de) | 2009-07-08 |
| US20090156798A1 (en) | 2009-06-18 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| R119 | Application deemed withdrawn, or ip right lapsed, due to non-payment of renewal fee | ||
| R119 | Application deemed withdrawn, or ip right lapsed, due to non-payment of renewal fee |
Effective date: 20140701 |