JPH0443697B2 - - Google Patents
Info
- Publication number
- JPH0443697B2 JPH0443697B2 JP61202661A JP20266186A JPH0443697B2 JP H0443697 B2 JPH0443697 B2 JP H0443697B2 JP 61202661 A JP61202661 A JP 61202661A JP 20266186 A JP20266186 A JP 20266186A JP H0443697 B2 JPH0443697 B2 JP H0443697B2
- Authority
- JP
- Japan
- Prior art keywords
- urea
- group
- imidazole
- adsorbent
- polymer
- 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
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 82
- 239000004202 carbamide Substances 0.000 claims description 81
- 239000003463 adsorbent Substances 0.000 claims description 55
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 49
- 125000002883 imidazolyl group Chemical group 0.000 claims description 44
- 229920000642 polymer Polymers 0.000 claims description 39
- 239000000178 monomer Substances 0.000 claims description 37
- 239000003431 cross linking reagent Substances 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 239000000470 constituent Substances 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000003827 glycol group Chemical group 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 31
- 238000001179 sorption measurement Methods 0.000 description 29
- ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 19
- -1 ethylene, propylene, 1-butene Chemical class 0.000 description 17
- 238000006116 polymerization reaction Methods 0.000 description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 14
- OSSNTDFYBPYIEC-UHFFFAOYSA-N 1-ethenylimidazole Chemical compound C=CN1C=CN=C1 OSSNTDFYBPYIEC-UHFFFAOYSA-N 0.000 description 11
- 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 10
- 210000003734 kidney Anatomy 0.000 description 10
- 238000000034 method Methods 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- OZAIFHULBGXAKX-VAWYXSNFSA-N AIBN Substances N#CC(C)(C)\N=N\C(C)(C)C#N OZAIFHULBGXAKX-VAWYXSNFSA-N 0.000 description 9
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 9
- 238000000862 absorption spectrum Methods 0.000 description 9
- 150000002334 glycols Chemical class 0.000 description 9
- 238000012360 testing method Methods 0.000 description 9
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 7
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 7
- 229920006037 cross link polymer Polymers 0.000 description 7
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- DBCAQXHNJOFNGC-UHFFFAOYSA-N 4-bromo-1,1,1-trifluorobutane Chemical compound FC(F)(F)CCCBr DBCAQXHNJOFNGC-UHFFFAOYSA-N 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 5
- 230000003247 decreasing effect Effects 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- 230000002522 swelling effect Effects 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 239000002245 particle Substances 0.000 description 4
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- MHQZDNQHLGFBRN-UHFFFAOYSA-N 5-ethenyl-1h-imidazole Chemical compound C=CC1=CNC=N1 MHQZDNQHLGFBRN-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 3
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 3
- 150000002430 hydrocarbons Chemical group 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 230000000379 polymerizing effect Effects 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- GRWFGVWFFZKLTI-IUCAKERBSA-N (-)-α-pinene Chemical compound CC1=CC[C@@H]2C(C)(C)[C@H]1C2 GRWFGVWFFZKLTI-IUCAKERBSA-N 0.000 description 2
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 2
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N 1-Heptene Chemical compound CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 2
- UZKWTJUDCOPSNM-UHFFFAOYSA-N 1-ethenoxybutane Chemical compound CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 2
- UAJRSHJHFRVGMG-UHFFFAOYSA-N 1-ethenyl-4-methoxybenzene Chemical compound COC1=CC=C(C=C)C=C1 UAJRSHJHFRVGMG-UHFFFAOYSA-N 0.000 description 2
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N 1-nonene Chemical compound CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 2
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 2
- JLIDVCMBCGBIEY-UHFFFAOYSA-N 1-penten-3-one Chemical compound CCC(=O)C=C JLIDVCMBCGBIEY-UHFFFAOYSA-N 0.000 description 2
- YYPNJNDODFVZLE-UHFFFAOYSA-N 3-methylbut-2-enoic acid Chemical compound CC(C)=CC(O)=O YYPNJNDODFVZLE-UHFFFAOYSA-N 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- IAQRGUVFOMOMEM-UHFFFAOYSA-N but-2-ene Chemical compound CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 2
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 2
- FUSUHKVFWTUUBE-UHFFFAOYSA-N buten-2-one Chemical compound CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 description 2
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 description 2
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- VHRYZQNGTZXDNX-UHFFFAOYSA-N methacryloyl chloride Chemical compound CC(=C)C(Cl)=O VHRYZQNGTZXDNX-UHFFFAOYSA-N 0.000 description 2
- JTHNLKXLWOXOQK-UHFFFAOYSA-N n-propyl vinyl ketone Natural products CCCC(=O)C=C JTHNLKXLWOXOQK-UHFFFAOYSA-N 0.000 description 2
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
- 150000002978 peroxides Chemical class 0.000 description 2
- 239000003505 polymerization initiator Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 239000012966 redox initiator Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 230000008961 swelling Effects 0.000 description 2
- 230000002195 synergetic effect Effects 0.000 description 2
- UAXOELSVPTZZQG-UHFFFAOYSA-N tiglic acid Natural products CC(C)=C(C)C(O)=O UAXOELSVPTZZQG-UHFFFAOYSA-N 0.000 description 2
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 2
- WTARULDDTDQWMU-RKDXNWHRSA-N (+)-β-pinene Chemical compound C1[C@H]2C(C)(C)[C@@H]1CCC2=C WTARULDDTDQWMU-RKDXNWHRSA-N 0.000 description 1
- WTARULDDTDQWMU-IUCAKERBSA-N (-)-Nopinene Natural products C1[C@@H]2C(C)(C)[C@H]1CCC2=C WTARULDDTDQWMU-IUCAKERBSA-N 0.000 description 1
- NIONDZDPPYHYKY-SNAWJCMRSA-N (2E)-hexenoic acid Chemical compound CCC\C=C\C(O)=O NIONDZDPPYHYKY-SNAWJCMRSA-N 0.000 description 1
- HMYXKHZCEYROAL-UHFFFAOYSA-N (4-chloro-2,3,5,6-tetrafluorophenyl)methanol Chemical compound OCC1=C(F)C(F)=C(Cl)C(F)=C1F HMYXKHZCEYROAL-UHFFFAOYSA-N 0.000 description 1
- ADLXTJMPCFOTOO-UHFFFAOYSA-N (E)-2-Nonenoic acid Natural products CCCCCCC=CC(O)=O ADLXTJMPCFOTOO-UHFFFAOYSA-N 0.000 description 1
- ADLXTJMPCFOTOO-BQYQJAHWSA-N (E)-non-2-enoic acid Chemical compound CCCCCC\C=C\C(O)=O ADLXTJMPCFOTOO-BQYQJAHWSA-N 0.000 description 1
- IICQZTQZQSBHBY-HWKANZROSA-N (e)-non-2-ene Chemical compound CCCCCC\C=C\C IICQZTQZQSBHBY-HWKANZROSA-N 0.000 description 1
- IBUCWFAQJINUGP-UHFFFAOYSA-N 1-(1h-imidazol-2-yl)-2-methylprop-2-en-1-one Chemical class CC(=C)C(=O)C1=NC=CN1 IBUCWFAQJINUGP-UHFFFAOYSA-N 0.000 description 1
- OHVLMTFVQDZYHP-UHFFFAOYSA-N 1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-2-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]ethanone Chemical compound N1N=NC=2CN(CCC=21)C(CN1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)=O OHVLMTFVQDZYHP-UHFFFAOYSA-N 0.000 description 1
- HMDQPBSDHHTRNI-UHFFFAOYSA-N 1-(chloromethyl)-3-ethenylbenzene Chemical compound ClCC1=CC=CC(C=C)=C1 HMDQPBSDHHTRNI-UHFFFAOYSA-N 0.000 description 1
- ZRZHXNCATOYMJH-UHFFFAOYSA-N 1-(chloromethyl)-4-ethenylbenzene Chemical compound ClCC1=CC=C(C=C)C=C1 ZRZHXNCATOYMJH-UHFFFAOYSA-N 0.000 description 1
- GXVWSABOPZBCGK-UHFFFAOYSA-N 1-butyl-5-ethenylimidazole Chemical compound CCCCN1C=NC=C1C=C GXVWSABOPZBCGK-UHFFFAOYSA-N 0.000 description 1
- BOVQCIDBZXNFEJ-UHFFFAOYSA-N 1-chloro-3-ethenylbenzene Chemical compound ClC1=CC=CC(C=C)=C1 BOVQCIDBZXNFEJ-UHFFFAOYSA-N 0.000 description 1
- KTZVZZJJVJQZHV-UHFFFAOYSA-N 1-chloro-4-ethenylbenzene Chemical compound ClC1=CC=C(C=C)C=C1 KTZVZZJJVJQZHV-UHFFFAOYSA-N 0.000 description 1
- OVGRCEFMXPHEBL-UHFFFAOYSA-N 1-ethenoxypropane Chemical compound CCCOC=C OVGRCEFMXPHEBL-UHFFFAOYSA-N 0.000 description 1
- VTPNYMSKBPZSTF-UHFFFAOYSA-N 1-ethenyl-2-ethylbenzene Chemical compound CCC1=CC=CC=C1C=C VTPNYMSKBPZSTF-UHFFFAOYSA-N 0.000 description 1
- NVZWEEGUWXZOKI-UHFFFAOYSA-N 1-ethenyl-2-methylbenzene Chemical compound CC1=CC=CC=C1C=C NVZWEEGUWXZOKI-UHFFFAOYSA-N 0.000 description 1
- VKVLTUQLNXVANB-UHFFFAOYSA-N 1-ethenyl-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1C=C VKVLTUQLNXVANB-UHFFFAOYSA-N 0.000 description 1
- XHUZSRRCICJJCN-UHFFFAOYSA-N 1-ethenyl-3-ethylbenzene Chemical compound CCC1=CC=CC(C=C)=C1 XHUZSRRCICJJCN-UHFFFAOYSA-N 0.000 description 1
- PECUPOXPPBBFLU-UHFFFAOYSA-N 1-ethenyl-3-methoxybenzene Chemical compound COC1=CC=CC(C=C)=C1 PECUPOXPPBBFLU-UHFFFAOYSA-N 0.000 description 1
- JZHGRUMIRATHIU-UHFFFAOYSA-N 1-ethenyl-3-methylbenzene Chemical compound CC1=CC=CC(C=C)=C1 JZHGRUMIRATHIU-UHFFFAOYSA-N 0.000 description 1
- WHFHDVDXYKOSKI-UHFFFAOYSA-N 1-ethenyl-4-ethylbenzene Chemical compound CCC1=CC=C(C=C)C=C1 WHFHDVDXYKOSKI-UHFFFAOYSA-N 0.000 description 1
- YFZHODLXYNDBSM-UHFFFAOYSA-N 1-ethenyl-4-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(C=C)C=C1 YFZHODLXYNDBSM-UHFFFAOYSA-N 0.000 description 1
- ATQUFXWBVZUTKO-UHFFFAOYSA-N 1-methylcyclopentene Chemical compound CC1=CCCC1 ATQUFXWBVZUTKO-UHFFFAOYSA-N 0.000 description 1
- KUIZKZHDMPERHR-UHFFFAOYSA-N 1-phenylprop-2-en-1-one Chemical compound C=CC(=O)C1=CC=CC=C1 KUIZKZHDMPERHR-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- OTTZHAVKAVGASB-HYXAFXHYSA-N 2-Heptene Chemical compound CCCC\C=C/C OTTZHAVKAVGASB-HYXAFXHYSA-N 0.000 description 1
- UIERETOOQGIECD-ARJAWSKDSA-M 2-Methyl-2-butenoic acid Natural products C\C=C(\C)C([O-])=O UIERETOOQGIECD-ARJAWSKDSA-M 0.000 description 1
- WYGWHHGCAGTUCH-UHFFFAOYSA-N 2-[(2-cyano-4-methylpentan-2-yl)diazenyl]-2,4-dimethylpentanenitrile Chemical compound CC(C)CC(C)(C#N)N=NC(C)(C#N)CC(C)C WYGWHHGCAGTUCH-UHFFFAOYSA-N 0.000 description 1
- CFVZILWIXKITDD-UHFFFAOYSA-N 2-acetyloxyprop-2-enoic acid Chemical compound CC(=O)OC(=C)C(O)=O CFVZILWIXKITDD-UHFFFAOYSA-N 0.000 description 1
- FEUFEGJTJIHPOF-UHFFFAOYSA-N 2-butyl acrylic acid Chemical compound CCCCC(=C)C(O)=O FEUFEGJTJIHPOF-UHFFFAOYSA-N 0.000 description 1
- ISRGONDNXBCDBM-UHFFFAOYSA-N 2-chlorostyrene Chemical compound ClC1=CC=CC=C1C=C ISRGONDNXBCDBM-UHFFFAOYSA-N 0.000 description 1
- PGYJSURPYAAOMM-UHFFFAOYSA-N 2-ethenoxy-2-methylpropane Chemical compound CC(C)(C)OC=C PGYJSURPYAAOMM-UHFFFAOYSA-N 0.000 description 1
- PIUJWWBOMGMSAY-UHFFFAOYSA-N 2-ethenoxybutane Chemical compound CCC(C)OC=C PIUJWWBOMGMSAY-UHFFFAOYSA-N 0.000 description 1
- PZBASOPBSCAZSR-UHFFFAOYSA-N 2-ethenyl-1-methylimidazole Chemical compound CN1C=CN=C1C=C PZBASOPBSCAZSR-UHFFFAOYSA-N 0.000 description 1
- MLMGJTAJUDSUKA-UHFFFAOYSA-N 2-ethenyl-1h-imidazole Chemical compound C=CC1=NC=CN1 MLMGJTAJUDSUKA-UHFFFAOYSA-N 0.000 description 1
- XUDBVJCTLZTSDC-UHFFFAOYSA-N 2-ethenylbenzoic acid Chemical compound OC(=O)C1=CC=CC=C1C=C XUDBVJCTLZTSDC-UHFFFAOYSA-N 0.000 description 1
- SLENVLASKTZHDW-UHFFFAOYSA-N 2-ethenylbenzonitrile Chemical compound C=CC1=CC=CC=C1C#N SLENVLASKTZHDW-UHFFFAOYSA-N 0.000 description 1
- RDQQZSMXQAMRFQ-UHFFFAOYSA-N 2-ethoxyethenyl acetate Chemical compound CCOC=COC(C)=O RDQQZSMXQAMRFQ-UHFFFAOYSA-N 0.000 description 1
- WROUWQQRXUBECT-UHFFFAOYSA-N 2-ethylacrylic acid Chemical compound CCC(=C)C(O)=O WROUWQQRXUBECT-UHFFFAOYSA-N 0.000 description 1
- NEYTTWNDEATJBU-UHFFFAOYSA-N 2-ethylpent-2-enoic acid Chemical compound CCC=C(CC)C(O)=O NEYTTWNDEATJBU-UHFFFAOYSA-N 0.000 description 1
- OTTZHAVKAVGASB-UHFFFAOYSA-N 2-heptene Natural products CCCCC=CC OTTZHAVKAVGASB-UHFFFAOYSA-N 0.000 description 1
- YURNCBVQZBJDAJ-UHFFFAOYSA-N 2-heptenoic acid Chemical compound CCCCC=CC(O)=O YURNCBVQZBJDAJ-UHFFFAOYSA-N 0.000 description 1
- IRUDSQHLKGNCGF-UHFFFAOYSA-N 2-methylhex-1-ene Chemical compound CCCCC(C)=C IRUDSQHLKGNCGF-UHFFFAOYSA-N 0.000 description 1
- PIAOLBVUVDXHHL-UHFFFAOYSA-N 2-nitroethenylbenzene Chemical compound [O-][N+](=O)C=CC1=CC=CC=C1 PIAOLBVUVDXHHL-UHFFFAOYSA-N 0.000 description 1
- ILPBINAXDRFYPL-UHFFFAOYSA-N 2-octene Chemical compound CCCCCC=CC ILPBINAXDRFYPL-UHFFFAOYSA-N 0.000 description 1
- WXBXVVIUZANZAU-UHFFFAOYSA-N 2E-decenoic acid Natural products CCCCCCCC=CC(O)=O WXBXVVIUZANZAU-UHFFFAOYSA-N 0.000 description 1
- IICQZTQZQSBHBY-UHFFFAOYSA-N 2t-nonene Natural products CCCCCCC=CC IICQZTQZQSBHBY-UHFFFAOYSA-N 0.000 description 1
- SGCFZIQBVRYXOZ-UHFFFAOYSA-N 3-but-3-enoyl-2-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=CC(C(=O)CC=C)=C1O SGCFZIQBVRYXOZ-UHFFFAOYSA-N 0.000 description 1
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Landscapes
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- External Artificial Organs (AREA)
Description
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çšãªæ°èŠé«ååå°¿çŽ åžçå€ã«é¢ãããDETAILED DESCRIPTION OF THE INVENTION [Industrial Field of Application] The present invention relates to a urea adsorbent, and particularly to a novel polymeric urea adsorbent useful for artificial kidneys.
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Artificial kidneys currently in use include dialysis-type, filtration-type, adsorption-type, and enzyme-immobilized artificial kidneys.
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ã§ãããã®ã¯éçºãããŠããªãã However, all of these have advantages and disadvantages, and no drug has been developed that is satisfactory for patients with chronic or acute renal failure.
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ããã For example, dialysis-type artificial kidneys are currently the most popular, but new dialysate is always required. In addition, these devices are generally large in size, resulting in the inconvenience that renal failure patients are confined in the hospital for long periods of time.
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ãã Filtration-type artificial kidneys have a major drawback in that serum containing useful components is also discarded.
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ãã Enzyme-immobilized artificial kidneys have been in particular progress in development recently, but there is a problem with the inactivation of the enzyme activity during or after urease immobilization, and its performance also depends on the surrounding environment such as temperature and acidity. Easily influenced by the environment.
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ã§ããã Adsorption-type artificial kidneys are small, lightweight, and simple, but they use activated carbon as an adsorbent, and although they are effective for organic wastes, they are completely ineffective against urea, which is the largest component excreted in urine. It has no effect. Currently, the search for urea removal substances is the most important issue in adsorption artificial kidneys. For example, there are applications of oxidized starch (Kobunshi Ronshu, Vol. 39, p. 629), urea adsorbents made by reacting formaldehyde or glyoxal with a polymer having a hydrazide group (Japanese Patent Application Laid-open No. 1983-69489), etc. However, the reality is that it has not yet reached the stage of practical use.
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As a result of intensive studies on high-performance urinary adsorbents to solve the above-mentioned problems, the present inventor found that a polymer containing both carboxyl groups and imidazole groups is useful as a urea removal substance, and polyoxyalkylene glycol The inventors discovered that a polymer containing a derivative as a constituent component has a higher urea adsorption ability, leading to the present invention. That is, the present invention provides: (1) a carboxyl group and an imidazole group represented by general formula (1); (In the formula, R 1 represents hydrogen or a hydrocarbon group having 5 or less carbon atoms.) A polymer of ethylenically unsaturated monomers that contains as a constituent component and is crosslinked with a crosslinking agent as necessary. , a polymer urea adsorbent characterized in that the ratio of the number of carboxyl groups to the number of imidazole groups (carboxyl group/imidazole group) is from 0.1 to 8.0.
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å€ã«é¢ããã(2) Carboxyl group, imidazole group represented by general formula (1) (In the formula, R 1 represents hydrogen or a hydrocarbon group having 5 or less carbon atoms.), and General formula (2) [-(CH 2 -) o O-] n R 2 (2) (In the formula, n is Contains a polyoxyalkylene glycol derivative group represented by an integer of 2 to 5, m represents an integer of 3 or more, and R2 represents hydrogen or a methyl group as a constituent component, and can be crosslinked with a crosslinking agent as necessary. A polymer of ethylenically unsaturated monomers having a ratio of the number of carboxyl groups to imidazole groups (carboxyl group/imidazole group) of 0.1.
The present invention relates to a polymer urea adsorbent characterized in that it has a molecular weight of 8.0 to 8.0.
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ãã®æ¹æ³ã«ãããŠã補é ããããšãã§ããã The urea adsorbent of the present invention can be easily produced by the following method. That is, an ethylenically unsaturated monomer having a carboxyl group or a group convertible to a carboxyl group and an ethylenically unsaturated monomer having an imidazole group shown in general formula (1). It is produced by radical polymerization by mixing at a certain molar ratio or by adding other ethylenically unsaturated monomers. The manufacturing method is arbitrary and is not particularly limited, and it can be manufactured by any of the bulk polymerization method, solution polymerization method, emulsion polymerization method, and suspension polymerization method.
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3-vinylsalicylic acid, 4-vinylsalicylic acid,
Styrenic unsaturated monomers such as 5-vinylsalicylic acid, 3-vinylacetylsalicylic acid, 4-vinylacetylsalicylic acid, and 5-vinylacetylsalicylic acid; Examples include functional unsaturated monomers, which can be used singly or in combination of two or more.
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Acid imidides, acid hydrazides, acid inorganic salts, α-angiericalactone, α-methylene-γ-
Unsaturated lactones such as butyrolactone and 2(5H)-furanone, unsaturated nitriles such as acrylonitrile and methacrylonitrile, etc. can also be used.
After polymerization, any of them can be converted into carboxyl groups by hydrolysis treatment. It is also possible to introduce a carboxyl group by an oxidation reaction after polymerization, but this causes undesirable side reactions such as cleavage of the main chain and ring-opening reaction of the imidazole group.
This is not preferred in the present invention.
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çšããããšãã§ããã In the present invention, other ethylenically unsaturated monomers can also be used in the production of the polymer if necessary, and even if they are carboxylic acid derivatives, they need to be converted into carboxyl groups after polymerization. For example, ethylene, propylene, 1-butene, 2-butene, 1-hexene, 2
-ethyl-1-butene, 1-methylcyclopentene, 1-heptene, 2-heptene, 2-methyl-
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Olefinic unsaturated monomers such as 2-octene, 1-nonene, 1-butene, 2-nonene, 3-nonene, 1-phenyl-2-pentene, α-pinene, β-pinene, chloroethylene, promoethylene ,
Halogenated ethylenically unsaturated monomers such as 1,1-dichloroethylene, 1,2-dichloroethylene, trifluoroethylene, styrene, o-methylstyrene, m-methylstyrene, p-methylstyrene, o-ethylstyrene, m -ethyl styrene, p
-ethylstyrene, o-chlorostyrene, m-chlorostyrene, p-chlorostyrene, m-chloromethylstyrene, p-chloromethylstyrene, o
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Styrenic unsaturated monomers such as nitrostyrene, p-nitrostyrene, o-cyanostyrene, m-cyanostyrene, p-cyanostyrene, methyl vinyl ether, ethyl vinyl ether, n-propyl vinyl ether, i-propyl vinyl ether, n- Vinyl ether unsaturated monomers such as butyl vinyl ether, sec-butyl vinyl ether, t-butyl vinyl ether, phenyl vinyl ether, methyl vinyl ketone, acetoxy vinyl ketone, ethyl vinyl ketone, n-propyl vinyl ketone, i-propyl vinyl ketone, Vinyl ketone unsaturated monomers such as phenyl vinyl ketone,
Vinyl ester unsaturated monomers such as vinyl acetate, ethoxyvinyl acetate, vinyl propionate, vinyl butyrate, vinyl laurate, vinyl palmitate, vinyl stearate, methyl (meth)acrylate, ethyl (meth)acrylate, n-propyl (meth)acrylate, n-butyl (meth)acrylate, n-amyl (meth)acrylate, n-hexyl (meth)acrylate, octyl (meth)acrylate, nonyl (meth)acrylate , (meth)decyl acrylate, (meth)dodecyl acrylate, (meth)
(meth)acrylic acid ester monomers such as oleyl acrylate and glycidyl (meth)acrylate;
In addition, monomers such as maleic anhydride, acrylonitrile, and acrylamide can be used as required, and one or more of these monomers can be used.
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ãªã³ãŒã«ã§ããã The radically polymerizable polyoxyalkylene glycol derivative represented by the general formula (3) used in the present invention is, for example, polyoxyethylene glycol mono(meth)acrylate, polyoxytrimethylene glycol (meth)acrylate, polyoxytetramethylene glycol mono (meth)acrylate, Ï-methoxypolyoxyethylene glycol mono(meth)acrylate, Ï-methoxypolyoxytrimethylene glycol mono(meth)acrylate, Ï-methoxypolyoxytetramethylene glycol mono(meth)acrylate, and general The radically polymerizable polyoxyalkylene glycol derivative represented by formula (4) is, for example, α-(p-
vinylbenzyloxy)-polyoxyethylene glycol, α-(p-vinylbenzyloxy)-polyoxytrimethylene glycol, α-(p-vinylbenzyloxy)-polytetramethylene glycol,
α-(p-vinylbenzyloxy)-Ï-methoxypolyoxyethylene glycol, α-(p-vinylbenzyloxy)-Ï-methoxypolyoxytrimethylene glycol, α-(p-vinylbenzyloxy)-Ï-methoxy It is polyoxytetramethylene glycol.
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ãçšããããšãã§ããã The radically polymerizable polyoxyalkylene glycol derivative represented by general formula (3) or (4) can be used simultaneously with other ethylenically unsaturated monomers, and if necessary, one or more types can be used. can be used.
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ã§ããªãã By introducing the polyoxyalkylene glycol derivative represented by the general formula (2) into the urea adsorbent of the present invention as a constituent component, it is possible to further exhibit urea adsorption ability due to the synergistic effect with the carboxyl group and imidazole group. can. The number average molecular weight of the radically polymerizable polyoxyalkylene glycol derivative represented by the general formula (3) or (4) used in the present invention is 120 or more, preferably 200 or more; No synergistic effects can be expected.
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ã³ç³»äžé£œååéäœãå¹æçã§ããã In the production of the polymeric urea adsorbent in the present invention, a crosslinking agent can also be used if necessary. As the crosslinking agent, for example, divinylbenzene, ethylene glycol (meth)acrylate, polyoxyethylene glycol (meth)acrylate, polydimethylsiloxane di(meth)acrylate, polyamide di(meth)acrylate, etc. can be used. The amount of the crosslinking agent to be used is 0.01% to 50% by weight based on the total weight, and if it is more than that, the lubricity of the produced urea adsorbent with respect to water will be significantly lowered, which is not preferable. Moreover, it is an absolute condition that the urea adsorbent of the present invention is insoluble in water, and therefore, in the case of a polymer that is soluble in water, it is necessary to use a crosslinking agent to make it insoluble.
Furthermore, even if a crosslinking agent is not used, insolubilization can be achieved by increasing the amount of other ethylenically unsaturated monomers, and olefinic unsaturated monomers and styrenic unsaturated monomers are particularly effective. be.
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ã«ã¯å°¿çŽ åžçèœã¯ä¹ããæå¹ã§ãªãã An example of manufacturing the urea adsorbent of the present invention will be shown. for example,
An example of the solution polymerization method is to dissolve equimolar amounts of methyl methacrylate, 1-vinylimidazole, acrylic acid, polyoxyethylene glycol monomethacrylate, and 1/10 molar equivalent of ethylene glycol dimethacrylate in a solvent, Polymerization is carried out using a polymerization initiator and stirring under a nitrogen stream. After the polymerization is completed, the mixture is poured into water to precipitate the polymer, followed by washing, drying, and pulverization to prepare a polymeric urea adhesive. The structure of the polymeric urea adsorbent is considered to be good, as the ratio of carboxyl groups to imidazole groups is considered to be 1 from the charging ratio, and the component represented by general formula (2) is 58% by weight of the total weight. It shows excellent urea adsorption function. In the present invention, the charged amount of an ethylenically unsaturated monomer having a carboxyl group or an ethylenically unsaturated monomer having a group convertible to a carboxyl group,
The charged amount of ethylenically unsaturated monomer having an imidazole group is 5% by weight of the total charged amount, respectively.
If either one is less than this, the urea adsorption ability is poor and is not effective.
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0.5ã§ãããæã奜ãŸããã¯r1ïŒïŒã§ããã The ratio of the number of carboxyl groups to the number of imidazole groups contained in the adsorbent in the present invention is r 1 =(number of carboxyl groups)/(number of imidazole groups), and is preferably r 1 =0.1 to 8. 1 = 2 to
0.5 and most preferably r 1 =1.
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ãæå¹ãªå°¿çŽ åžçèœã瀺ãã When r 1 =1, the urea adsorbent of the present invention exhibits the most effective urea adsorption ability.
r1ã0.1ããå°ããå Žåã«ããïŒãã倧ããå Ž
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ã§ããªãã By introducing the component represented by general formula (2) into this product, it becomes possible to further improve the urea adsorption ability. For this purpose, the component represented by general formula (2) must be at least 2% by weight or more than 70% by weight of the total weight.
It is as follows. If it is less than 2% by weight, the effect cannot be expected.
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ãã Moreover, the water absorption of the produced urea adsorbent increases to 70% by weight or more, causing inconvenience in handling.
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ã³ãŸã€ã«âãžã¡ãã«ã¢ããªã³çããããããã A polymerization initiator is used in producing the urea adsorbent, but there is no particular limitation, and any of azo compounds, peroxides, redox initiators, etc. can be used. For example, azo compounds include α,α'-azobisisobutyronitrile, 2,2'-azobis-(2,4-dimethylvaleronitrile), and peroxides include:
dibenzoyl peroxide, lauroyl peroxide, di-t-butyl peroxide, dicumyl peroxide, t-butyl hydroperoxide,
Examples include diisopropyl peroxide carbonate, and redox initiators include hydrogen peroxide-Fe 2+ salt, persulfate-sodium bisulfite,
Examples include cumene hydroperoxide-Fe 2+ salt, benzoyl peroxide-dimethylaniline, and the like.
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ã®ã±ãã³ç³»æº¶å€ã䜿çšãããã The solvent used in the solution polymerization method is not limited in any way as long as it can dissolve the monomer and does not inhibit polymerization, such as N,
Amide solvents such as N'-dimethylformamide and N,N'-dimethylacetamide, aromatic hydrocarbons such as benzene, toluene and xylene, ester solvents such as methyl acetate, ethyl acetate, propyl acetate and butyl acetate, methanol , ethanol, isopropyl alcohol, n-propyl alcohol,
Alcohol solvents such as n-butanol, isobutanol, sec-butanol and t-butanol, and ketone solvents such as acetone, methyl ethyl ketone and diethyl ketone are used.
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100äžã奜ãŸããã¯5000ä¹è³10äžã§ããã In order to obtain spherical polymer particles, suspension polymerization or emulsion polymerization can be used. In these cases, polymerization can be carried out using water as a solvent and a dispersion stabilizer or surfactant. It is possible.
(Japanese Unexamined Patent Publication No. 1983-55009, Japanese Patent Application No. 171760) The molecular weight of the polymer of the adsorbent of the present invention is 3000 to 3000.
1 million, preferably 5,000 to 100,000.
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ççã®åŠçåŸå°¿çŽ åžçå€ãšããŠäœ¿çšããŠãããã The urea adsorbent produced as described above can be used as an adsorbent as is,
If necessary, it may be used as a urea adsorbent after carrying out a surface modification reaction, coating with heparin or albumin, plasma treatment, or the like.
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The polymer urea adsorbent of the present invention has a high urea adsorption capacity (100 mg/dl), and by adding 0.5 g of the urea adsorbent to 50 ml of urea aqueous solution and soaking it for 2 hours, the urea concentration can be reduced to 25 mg. /dl), which can be applied to adsorption-type artificial kidneys and sensors.
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EXAMPLES Hereinafter, the present invention will be specifically explained with reference to Examples, but the present invention is not limited to these Examples.
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ããèšæœ€åºŠã¯è¯å¥œã§ãããExample 1 Acrylic acid 7.5g, 1-vinylimidazole 9.4g
g, 2 g of ethylene glycol methacrylate,
α,αâ²-Azopisisobutyronitrile (AIBN)
0.1 g was dissolved in 100 ml of N,N'-dimethylformaldehyde (DMF) and polymerized at 110° C. for 2 hours under a nitrogen stream. Thereafter, a small amount of AIBN was added, and DMF was distilled off under reduced pressure and heating to complete the polymerization reaction. The polymerization residue was placed in the water from step 1 and stirred at room temperature for 1 hour, and then the polymerization product was separated using a centrifuge, which was further washed twice with water, twice with methanol, and once with acetone. , 50â under reduced pressure
I let it dry for a day. After drying, grind to an average particle size of approx.
100Ό particles were obtained. The composition of the polymer was determined by infrared absorption spectrum to show carboxyl groups (3300 to 300
cm -1 , 1750cm -1 ) and imidazole group (1550,
1490, 1325 cm -1 ) was confirmed, and the ratio of the number of carboxyl groups to the number of imidazole groups is considered to be 1 from the amount charged. The carboxyl groups and imidazole groups interact weakly within the polymer, but are arranged randomly in consideration of the absorption range of the infrared absorption spectrum. Further, the polymer is a crosslinked polymer and is insoluble in all solvents, but has a good degree of swelling in water.
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ããå°¿çŽ åžçéã以äžã®åŠãã«ããŠæž¬å®ããã The polymer particles were used as they were as a urea adsorbent, and the amount of urea adsorbed was measured as follows.
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Colorimetric determination was carried out at 480 nm using a 150-20 spectrophotometer. ) As a result, it was found that the urea concentration had decreased to 30mg urea/dl. For comparison, when activated carbon was used instead of the adsorbent, the amount decreased to only 95 mg urea/dl.
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ãŠããäºå®ãåãã€ãã It has thus been found that the ratio of the number of carboxyl groups to the number of imidazole groups is 1, and that a polymer composed only of both has a very high urea adsorption function.
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Ultraviolet/visible absorption spectrum is 150 manufactured by Hitachi, Ltd.
Measurements were made using a -20 type ultraviolet/visible spectrophotometer.
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ãå°¿çŽ åžçèœãæããŠããäºå®ãåãã€ããExample 2 10 g of 1-vinylimidazole and 11.0 g of methacrylic acid chloride were added to 50 ml of toluene and stirred at room temperature for 1 hour to form a white precipitate. This white precipitate is a methacryloyl imidazole salt, which is a 1:1 salt of methacryloyl group and 1-vinylimidazole. The imidazole salt was filtered and dissolved in 100 ml of DMF, to which were added 1 g of divinylbenzene and 0.1 g of AIBN, and polymerization was carried out at 110° C. for 2 hours. Thereafter, a small amount of AIBN was added, and DMF was distilled off under reduced pressure and heating to complete the polymerization reaction. The polymerization residue was placed in water from Step 1 and stirred at room temperature for 5 hours, and then neutralized by adding sodium hydrogen carbonate until no carbon dioxide was released. At this point, the carboxyl group and imidazole group were liberated, and the presence of the carboxyl group and imidazole group was confirmed by infrared absorption spectrum. Thereafter, separation, purification, drying, and powder frame were performed in the same manner as in Example 1 to obtain a urea adsorbent. The polymer contains carboxyl groups and imidazole groups, and the ratio is thought to be 1 based on the charging ratio.It is also a polymer crosslinked with divinylbenzene, and is insoluble in all solvents, but has a high degree of swelling in water. is in good condition.
A urea adsorption test was conducted using the adsorbent. As a result, it was found that the urea concentration had decreased to 30 mg urea/dl. In this way, it has been found that a urea adsorbent obtained by first synthesizing a salt from methacrylic acid chloride and 1-vinylimidazole and then polymerizing it also has a very high urea adsorption capacity.
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ãšãåãããExample 3 1-vinylimidazole 10g, acrylic acid 7.9g
g, 20 g of polyoxyethylene glycol monomethacrylate (Blenmar PE350, number average molecular weight 400, manufactured by NOF Corporation), 2 g of ethylene glycol dimethacrylate, and 0.1 g of AIBN were dissolved in 100 ml of DMF, and a urea adsorbent was added in the same manner as in Example 1. It was adjusted. According to the infrared absorption spectrum, the adsorbent contains carboxyl groups, imidazole groups, and hydroxyl groups (3500 to 3300
cm -1 ) was confirmed, and the ratio of carboxyl groups to imidazole groups was 1 depending on the preparation ratio.
It is a polymer in which the polyoxyethylene glycol derivative is present at 50% by weight of the total weight. Furthermore, it is a crosslinked polymer and is insoluble in all solvents, but
The water swelling property is good and better than that of Example 1. When a urea adsorption test was conducted using the adsorbent in the same manner as in Example 1, it was found that the adsorption amount was reduced to 25 mg urea/dl. Thus, it can be seen that when a polyoxyethylene glycol derivative is contained, the urea adsorption ability is improved.
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å€ã¯é«ãåžçèœã瀺ãããšãåããExample 4 2 g of methacrylic acid, 2 g of 4-vinylimidazole, polyoxyethylene glycol monomethacrylate (Blemmer PE350, number average molecular weight 400,
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A urea adsorbent was prepared by dissolving it in DMF and using the same method as in Example 1. By infrared absorption spectrum,
The adsorbent contains a carboxyl group, an imidazole group,
It was confirmed that hydroxyl groups and hydroxyl groups were contained, and it was further confirmed that a free -NH group (3210 cmp -1 , sharp absorption) was present. This polymer is a polymer in which the ratio of carboxyl groups to imidazole groups is 1 depending on the charging ratio, and the polyoxyethylene glycol derivative is present in an amount of 50% by weight of the total weight. Furthermore, it is a crosslinked polymer and is insoluble in all solvents, but has good swelling properties in water. When a urea adsorption test was carried out using the adsorbent in the same manner as in Example 1, it was found that the urea adsorption was reduced to 37 mg urea/dl. Thus, it can be seen that even when 4-vinylimidazole is used as the unsaturated monomer having an imidazole group, the urea absorbent of the present invention exhibits high adsorption capacity.
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A urea adsorbent was prepared by dissolving in 100 ml of DMF and using the same method as in Example 1. Infrared absorption spectra revealed that the adsorbent contains carboxyl groups, imidazole groups, and methyl methacrylate polymerization residues (C=O, 1735 cm
-1 ), and it is a polymer composed of carboxyl groups, imidazole groups, and methyl methacrylate polymer residues in a 1:1:1 ratio depending on the charging ratio. The polymer is a crosslinked polymer and is insoluble in all solvents, but has good swelling properties in water. When a urea adsorption test was conducted using the adsorbent in the same manner as in Example 1, 35
It was found that the concentration had decreased to mg urea/dl.
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é«ãåžçèœã瀺ãããšãåãã In addition, using 3.2 g of vinyl acetate instead of the above methyl methacrylate, a polymer in which the number of carboxyl groups, the number of imidazole groups, and the number of vinyl acetate polymerization residues were in a 1:1:1 ratio was synthesized by the same method. A urea adsorbent was prepared. When a urea adsorption test was conducted using the adsorbent in the same manner as in Example 1, it was found that the adsorption amount was reduced to 38 mg urea/dl. Thus, it can be seen that the urea adsorbent of the present invention exhibits high adsorption capacity even when other ethylenically unsaturated monomer polymerization residues are present in addition to carboxyl groups and imidazole groups.
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ãããŠãå°¿çŽ åžçèœã¯åªããŠããããšãåããExample 6 30 g of styrene, 9.4 g of 1-vinylimidazole,
A urea adsorbent was prepared in the same manner as in Example 1 by dissolving 7.5 g of acrylic acid and 0.1 g of AIBN in 100 ml of DMF.
The adsorbent is a non-crosslinked polymer and is soluble in solvents such as DMF and dimethylacetamide, but is soluble in water,
It is a polymer that is insoluble in methanol and ethanol. Further, the number average molecular weight of the adsorbent is about 12,000, and the presence of carboxyl groups and imidazole groups was confirmed by infrared absorption spectrum, and their absence is considered to be 1 based on the charging ratio. When a urea adsorption test was carried out using the adsorbent in the same manner as in Example 1, it was found that the adsorption amount had decreased to 41 mg urea/dl. The adsorbent used in this example is a non-crosslinked polymer whose main component is polystyrene, which has a higher swelling property in water than a crosslinked polymer, and also has excellent urea adsorption ability. I understand.
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ã¿ã§ãããComparative example 1-vinylimidazole 10g, ethylene glycol dimethacrylate 1g, AIBN 0.03g
It was dissolved in 50 ml of DMF and polymerized in the same manner as in Example 1 to prepare a urea adsorbent. When a urea adsorption test was conducted using the adsorbent in the same manner as in Example 1,
The urea concentration remained 100 mg urea/dl even after the test, and no change was observed. It was found that the polymer had no carboxyl groups, only imidazole groups, and had no urea adsorption ability at all. Further, although this polymer is insoluble in all polymers, it also has poor swelling property in water and is not suitable as a urea adsorbent. Also, above 1-
A urea adsorbent was prepared by polymerizing in the same manner as in Example 1 using 10 g of acrylic acid instead of vinyl imidazole. When a urea adsorption test was carried out using the adsorbent in the same manner as in Example 1, it was found that it had very high hygroscopicity and was difficult to handle, and that the urea concentration could only be reduced to 60 mg urea/dl. Divided. This polymer has no imidazole group and only carboxyl groups.
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ãã These facts indicate that polymers containing only carboxyl groups or only imidazole groups are unsuitable as urea adsorbents in the present invention.
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The polymer urea adsorbent of the present invention contains both a carboxyl group and an imidazole group,
It has a high-performance urea function and can be applied to all fields that require urea adsorption and separation, and is particularly applicable to adsorption-type artificial kidneys and sensors.
Claims (1)
ãŸãŒã«åº ïŒåŒäžãR1ã¯æ°ŽçŽ ãŸãã¯ççŽ æ°ïŒä»¥äžã®çåæ°Ž
çŽ åºãè¡šããïŒ ãæ§ææåãšããŠå«æããå¿ èŠã«å¿ããŠæ¶æ©å€ã«
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0.1ä¹è³0.8ã§ããããšãç¹åŸŽãšããé«ååå°¿çŽ åž
çå€ã ïŒ ã«ã«ããã·ã«åºã äžè¬åŒ(1)ã§ç€ºãããã€ãããŸãŒã«åº ïŒåŒäžãR1ã¯æ°ŽçŽ ãŸãã¯ççŽ æ°ïŒä»¥äžã®çåæ°Ž
çŽ åºãè¡šããïŒãåã³ äžè¬åŒ(2) ãâïŒCH2âïŒoâãnR2 (2) ïŒåŒäžïœã¯ïŒä¹è³ïŒã®æŽæ°ãïœã¯ïŒä»¥äžã®æŽæ°ã
è¡šããR2ã¯æ°ŽçŽ ãŸãã¯ã¡ãã«åºãè¡šããïŒã§ç€ºã
ããããªãªãã·ã¢ã«ãã¬ã³ã°ãªã³ãŒã«èªå°äœåº ãæ§ææåãšããŠå«æããå¿ èŠã«å¿ããŠæ¶æ©å€ã«
ããæ¶æ©ãããšãã¬ã³æ§äžé£œååéäœã®éåäœã§
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æ°ãšã®æ¯ïŒã«ã«ããã·ã«åºïŒã€ãããŸãŒã«åºïŒ
ãã0.1ä¹è³8.0ã§ããããšãç¹åŸŽãšããé«ååå°¿
çŽ åžçå€ã[Claims] 1. Carboxyl group and imidazole group represented by general formula (1) (In the formula, R 1 represents hydrogen or a hydrocarbon group having 5 or less carbon atoms.) A polymer of ethylenically unsaturated monomers that contains as a constituent component and is crosslinked with a crosslinking agent as necessary. , the ratio of the number of carboxyl groups to the number of imidazole groups (carboxyl group/imidazole group) is
A polymer urea adsorbent characterized by having a molecular weight of 0.1 to 0.8. 2 carboxyl group, imidazole group represented by general formula (1) (In the formula, R 1 represents hydrogen or a hydrocarbon group having 5 or less carbon atoms.), and General formula (2) [-(CH 2 -) o O-] n R 2 (2) (In the formula, n is Contains a polyoxyalkylene glycol derivative group represented by an integer of 2 to 5, m represents an integer of 3 or more, and R2 represents hydrogen or a methyl group as a constituent component, and can be crosslinked with a crosslinking agent as necessary. A polymer of ethylenically unsaturated monomers, the ratio of the number of carboxyl groups to the number of imidazole groups (carboxyl group/imidazole group)
is from 0.1 to 8.0.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61202661A JPS6359353A (en) | 1986-08-30 | 1986-08-30 | High-molecular urea adsorbent |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61202661A JPS6359353A (en) | 1986-08-30 | 1986-08-30 | High-molecular urea adsorbent |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6359353A JPS6359353A (en) | 1988-03-15 |
| JPH0443697B2 true JPH0443697B2 (en) | 1992-07-17 |
Family
ID=16461047
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP61202661A Granted JPS6359353A (en) | 1986-08-30 | 1986-08-30 | High-molecular urea adsorbent |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6359353A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2013528103A (en) * | 2010-06-07 | 2013-07-08 | ãã¬ãŒããŠã¹ ã¡ãã£ã«ã« ã±ã¢ ããŒã«ãã£ã³ã°ã¹ ã€ã³ã³ãŒãã¬ã€ããã | Urea adsorbent |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6861473B2 (en) | 2003-02-28 | 2005-03-01 | Baxter International Inc. | Macromolecular ketoaldehydes |
| JP5233146B2 (en) * | 2007-03-30 | 2013-07-10 | æ ç°å·¥æ¥æ ªåŒäŒç€Ÿ | ORGANIC UREA COMPOUND ADSORBENT, ORGANIC UREA COMPOUND ADSORBING DEVICE, AND ORGANIC UREA COMPOUND TREATMENT METHOD |
| US8220643B2 (en) * | 2008-06-06 | 2012-07-17 | Fresenius Medical Care Holdings, Inc. | Urea sorbent |
| US20120032093A1 (en) | 2010-08-03 | 2012-02-09 | Kemira Chemicals Inc. | Tagged scale inhibitor compositions and methods of inhibiting scale |
-
1986
- 1986-08-30 JP JP61202661A patent/JPS6359353A/en active Granted
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2013528103A (en) * | 2010-06-07 | 2013-07-08 | ãã¬ãŒããŠã¹ ã¡ãã£ã«ã« ã±ã¢ ããŒã«ãã£ã³ã°ã¹ ã€ã³ã³ãŒãã¬ã€ããã | Urea adsorbent |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6359353A (en) | 1988-03-15 |
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