JP5558824B2 - 吸水性樹脂の製造方法 - Google Patents
吸水性樹脂の製造方法 Download PDFInfo
- Publication number
- JP5558824B2 JP5558824B2 JP2009538002A JP2009538002A JP5558824B2 JP 5558824 B2 JP5558824 B2 JP 5558824B2 JP 2009538002 A JP2009538002 A JP 2009538002A JP 2009538002 A JP2009538002 A JP 2009538002A JP 5558824 B2 JP5558824 B2 JP 5558824B2
- Authority
- JP
- Japan
- Prior art keywords
- water
- absorbent resin
- group
- mass
- added
- 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.)
- Active
Links
- 239000011347 resin Substances 0.000 title claims description 114
- 229920005989 resin Polymers 0.000 title claims description 114
- 239000002250 absorbent Substances 0.000 title claims description 89
- 238000004519 manufacturing process Methods 0.000 title claims description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 title description 113
- 230000002745 absorbent Effects 0.000 title description 38
- -1 oxetane compound Chemical class 0.000 claims description 109
- 239000002243 precursor Substances 0.000 claims description 48
- 239000000178 monomer Substances 0.000 claims description 42
- 238000006243 chemical reaction Methods 0.000 claims description 41
- 238000004132 cross linking Methods 0.000 claims description 25
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 3
- 230000000379 polymerizing effect Effects 0.000 claims description 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 66
- 239000003431 cross linking reagent Substances 0.000 description 34
- 238000000034 method Methods 0.000 description 27
- 238000010521 absorption reaction Methods 0.000 description 26
- 239000007864 aqueous solution Substances 0.000 description 26
- 238000006116 polymerization reaction Methods 0.000 description 26
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 22
- 238000001035 drying Methods 0.000 description 20
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 239000000203 mixture Substances 0.000 description 14
- 239000002504 physiological saline solution Substances 0.000 description 14
- 239000000463 material Substances 0.000 description 13
- 238000003756 stirring Methods 0.000 description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 229910001873 dinitrogen Inorganic materials 0.000 description 12
- 238000010992 reflux Methods 0.000 description 12
- 235000014113 dietary fatty acids Nutrition 0.000 description 11
- 239000000194 fatty acid Substances 0.000 description 11
- 229930195729 fatty acid Natural products 0.000 description 11
- 229940098779 methanesulfonic acid Drugs 0.000 description 11
- 239000002904 solvent Substances 0.000 description 11
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 11
- 230000015572 biosynthetic process Effects 0.000 description 10
- 239000003921 oil Substances 0.000 description 10
- 239000007870 radical polymerization initiator Substances 0.000 description 10
- 238000003786 synthesis reaction Methods 0.000 description 10
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- HMPHJJBZKIZRHG-UHFFFAOYSA-N chloromethanesulfonic acid Chemical compound OS(=O)(=O)CCl HMPHJJBZKIZRHG-UHFFFAOYSA-N 0.000 description 8
- 229920001577 copolymer Polymers 0.000 description 8
- 238000004821 distillation Methods 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- 239000003209 petroleum derivative Substances 0.000 description 8
- 230000000704 physical effect Effects 0.000 description 8
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 7
- 239000000706 filtrate Substances 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- 239000002245 particle Substances 0.000 description 7
- 229920000742 Cotton Polymers 0.000 description 6
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000004094 surface-active agent Substances 0.000 description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 5
- 239000004677 Nylon Substances 0.000 description 5
- 229910052783 alkali metal Inorganic materials 0.000 description 5
- ZIUHHBKFKCYYJD-UHFFFAOYSA-N n,n'-methylenebisacrylamide Chemical compound C=CC(=O)NCNC(=O)C=C ZIUHHBKFKCYYJD-UHFFFAOYSA-N 0.000 description 5
- 229920001778 nylon Polymers 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- 239000011780 sodium chloride Substances 0.000 description 5
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 4
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
- 239000002270 dispersing agent Substances 0.000 description 4
- 229920001971 elastomer Polymers 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- 238000006386 neutralization reaction Methods 0.000 description 4
- 230000003472 neutralizing effect Effects 0.000 description 4
- 239000005060 rubber Substances 0.000 description 4
- 239000002002 slurry Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- UNMJLQGKEDTEKJ-UHFFFAOYSA-N (3-ethyloxetan-3-yl)methanol Chemical compound CCC1(CO)COC1 UNMJLQGKEDTEKJ-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000004698 Polyethylene Substances 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- UCQFCFPECQILOL-UHFFFAOYSA-N diethyl hydrogen phosphate Chemical compound CCOP(O)(=O)OCC UCQFCFPECQILOL-UHFFFAOYSA-N 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 235000019441 ethanol Nutrition 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 3
- 150000002921 oxetanes Chemical class 0.000 description 3
- 229920000573 polyethylene Polymers 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 238000010558 suspension polymerization method Methods 0.000 description 3
- 238000010557 suspension polymerization reaction Methods 0.000 description 3
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- LCPVQAHEFVXVKT-UHFFFAOYSA-N 2-(2,4-difluorophenoxy)pyridin-3-amine Chemical compound NC1=CC=CN=C1OC1=CC=C(F)C=C1F LCPVQAHEFVXVKT-UHFFFAOYSA-N 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 2
- KKUKTXOBAWVSHC-UHFFFAOYSA-N Dimethylphosphate Chemical compound COP(O)(=O)OC KKUKTXOBAWVSHC-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000001856 Ethyl cellulose Substances 0.000 description 2
- ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 239000004716 Ethylene/acrylic acid copolymer Substances 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- 206010021639 Incontinence Diseases 0.000 description 2
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- 229930006000 Sucrose Natural products 0.000 description 2
- SZYSLWCAWVWFLT-UTGHZIEOSA-N [(2s,3s,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)-2-[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxolan-2-yl]methyl octadecanoate Chemical compound O([C@@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)[C@]1(COC(=O)CCCCCCCCCCCCCCCCC)O[C@H](CO)[C@@H](O)[C@@H]1O SZYSLWCAWVWFLT-UTGHZIEOSA-N 0.000 description 2
- LXEKPEMOWBOYRF-UHFFFAOYSA-N [2-[(1-azaniumyl-1-imino-2-methylpropan-2-yl)diazenyl]-2-methylpropanimidoyl]azanium;dichloride Chemical compound Cl.Cl.NC(=N)C(C)(C)N=NC(C)(C)C(N)=N LXEKPEMOWBOYRF-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 150000005215 alkyl ethers Chemical class 0.000 description 2
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium peroxydisulfate Substances [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 2
- VAZSKTXWXKYQJF-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)OOS([O-])=O VAZSKTXWXKYQJF-UHFFFAOYSA-N 0.000 description 2
- 229910001870 ammonium persulfate Inorganic materials 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- 238000010533 azeotropic distillation Methods 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 239000004359 castor oil Substances 0.000 description 2
- 235000019438 castor oil Nutrition 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000012986 chain transfer agent Substances 0.000 description 2
- 230000018044 dehydration Effects 0.000 description 2
- 238000006297 dehydration reaction Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 2
- HQQADJVZYDDRJT-UHFFFAOYSA-N ethene;prop-1-ene Chemical group C=C.CC=C HQQADJVZYDDRJT-UHFFFAOYSA-N 0.000 description 2
- 229920001249 ethyl cellulose Polymers 0.000 description 2
- 235000019325 ethyl cellulose Nutrition 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 2
- 229920000578 graft copolymer Polymers 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical class C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
- GDOPTJXRTPNYNR-UHFFFAOYSA-N methylcyclopentane Chemical compound CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 229920001155 polypropylene Polymers 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 235000019260 propionic acid Nutrition 0.000 description 2
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 2
- CHQMHPLRPQMAMX-UHFFFAOYSA-L sodium persulfate Substances [Na+].[Na+].[O-]S(=O)(=O)OOS([O-])(=O)=O CHQMHPLRPQMAMX-UHFFFAOYSA-L 0.000 description 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
- 239000000600 sorbitol Substances 0.000 description 2
- 239000005720 sucrose Substances 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 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
- NLQMSBJFLQPLIJ-UHFFFAOYSA-N (3-methyloxetan-3-yl)methanol Chemical compound OCC1(C)COC1 NLQMSBJFLQPLIJ-UHFFFAOYSA-N 0.000 description 1
- SGTQXKBRULHMLI-UHFFFAOYSA-N (methyl-$l^{2}-phosphanyl)methane Chemical compound C[P]C SGTQXKBRULHMLI-UHFFFAOYSA-N 0.000 description 1
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical group CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 1
- MYECVPCGFLCGQX-UHFFFAOYSA-N 2-[(1-amino-2-methyl-1-phenyliminopropan-2-yl)diazenyl]-2-methyl-n'-phenylpropanimidamide;dihydrochloride Chemical compound Cl.Cl.C=1C=CC=CC=1NC(=N)C(C)(C)N=NC(C)(C)C(=N)NC1=CC=CC=C1 MYECVPCGFLCGQX-UHFFFAOYSA-N 0.000 description 1
- AEZBIUBWOJAYOA-UHFFFAOYSA-N 2-[2-[2-[2-[1-(2-hydroxyethyl)-4,5-dihydroimidazol-2-yl]propan-2-yldiazenyl]propan-2-yl]-4,5-dihydroimidazol-1-yl]ethanol Chemical compound N=1CCN(CCO)C=1C(C)(C)N=NC(C)(C)C1=NCCN1CCO AEZBIUBWOJAYOA-UHFFFAOYSA-N 0.000 description 1
- KRDXTHSSNCTAGY-UHFFFAOYSA-N 2-cyclohexylpyrrolidine Chemical compound C1CCNC1C1CCCCC1 KRDXTHSSNCTAGY-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- AUZRCMMVHXRSGT-UHFFFAOYSA-N 2-methylpropane-1-sulfonic acid;prop-2-enamide Chemical compound NC(=O)C=C.CC(C)CS(O)(=O)=O AUZRCMMVHXRSGT-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
- VFXXTYGQYWRHJP-UHFFFAOYSA-N 4,4'-azobis(4-cyanopentanoic acid) Chemical compound OC(=O)CCC(C)(C#N)N=NC(C)(CCC(O)=O)C#N VFXXTYGQYWRHJP-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 229940126062 Compound A Drugs 0.000 description 1
- 239000004641 Diallyl-phthalate Substances 0.000 description 1
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 description 1
- 208000010201 Exanthema Diseases 0.000 description 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 1
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 1
- 241000257303 Hymenoptera Species 0.000 description 1
- 239000002211 L-ascorbic acid Substances 0.000 description 1
- 235000000069 L-ascorbic acid Nutrition 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
- 239000005062 Polybutadiene Substances 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 229920001214 Polysorbate 60 Polymers 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 108010009736 Protein Hydrolysates Proteins 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- MZVQCMJNVPIDEA-UHFFFAOYSA-N [CH2]CN(CC)CC Chemical group [CH2]CN(CC)CC MZVQCMJNVPIDEA-UHFFFAOYSA-N 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000003926 acrylamides Chemical class 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 150000001346 alkyl aryl ethers Chemical class 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 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 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- KQDDQXNVESLJNO-UHFFFAOYSA-N chloromethanesulfonyl chloride Chemical compound ClCS(Cl)(=O)=O KQDDQXNVESLJNO-UHFFFAOYSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 201000005884 exanthem Diseases 0.000 description 1
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 239000012770 industrial material Substances 0.000 description 1
- FPNCFEPWJLGURZ-UHFFFAOYSA-L iron(2+);sulfite Chemical compound [Fe+2].[O-]S([O-])=O FPNCFEPWJLGURZ-UHFFFAOYSA-L 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 125000005641 methacryl group Chemical group 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- WVFLGSMUPMVNTQ-UHFFFAOYSA-N n-(2-hydroxyethyl)-2-[[1-(2-hydroxyethylamino)-2-methyl-1-oxopropan-2-yl]diazenyl]-2-methylpropanamide Chemical compound OCCNC(=O)C(C)(C)N=NC(C)(C)C(=O)NCCO WVFLGSMUPMVNTQ-UHFFFAOYSA-N 0.000 description 1
- BUGISVZCMXHOHO-UHFFFAOYSA-N n-[1,3-dihydroxy-2-(hydroxymethyl)propan-2-yl]-2-[[1-[[1,3-dihydroxy-2-(hydroxymethyl)propan-2-yl]amino]-2-methyl-1-oxopropan-2-yl]diazenyl]-2-methylpropanamide Chemical compound OCC(CO)(CO)NC(=O)C(C)(C)N=NC(C)(C)C(=O)NC(CO)(CO)CO BUGISVZCMXHOHO-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000010534 nucleophilic substitution reaction Methods 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 125000003566 oxetanyl group Chemical group 0.000 description 1
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- JRKICGRDRMAZLK-UHFFFAOYSA-L persulfate group Chemical group S(=O)(=O)([O-])OOS(=O)(=O)[O-] JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 1
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical class O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical class OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 239000005056 polyisocyanate Substances 0.000 description 1
- 229920001228 polyisocyanate Polymers 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229940051841 polyoxyethylene ether Drugs 0.000 description 1
- 229920000056 polyoxyethylene ether Polymers 0.000 description 1
- 229920002503 polyoxyethylene-polyoxypropylene Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 206010037844 rash Diseases 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000007717 redox polymerization reaction Methods 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 150000003333 secondary alcohols Chemical class 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 229940079827 sodium hydrogen sulfite Drugs 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000012798 spherical particle Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 229920001897 terpolymer Polymers 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
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Images
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
- 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
- B01J20/265—Synthetic macromolecular compounds modified or post-treated polymers
- B01J20/267—Cross-linked polymers
-
- 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
-
- 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
- C08J3/00—Processes of treating or compounding macromolecular substances
- C08J3/24—Crosslinking, e.g. vulcanising, of macromolecules
- C08J3/245—Differential crosslinking of one polymer with one crosslinking type, e.g. surface crosslinking
-
- 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)
- Absorbent Articles And Supports Therefor (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Processes Of Treating Macromolecular Substances (AREA)
Description
1 ビュレット部
10 ビュレット
11 空気導入管
12 コック
13 コック
14 ゴム栓
2 導管
3 測定台
4 測定部
40 円筒
41 ナイロンメッシュ
42 重り
5 吸水性樹脂
吸水性樹脂2.0gを、綿袋(メンブロード60番、横100mm×縦200mm)中に計り取り、500mL容のビーカー中に入れた。綿袋に生理食塩水(0.9質量%塩化ナトリウム水溶液、以下同様)500gを一度に注ぎ込み、吸水性樹脂のママコが発生しないように生理食塩水を分散させた。綿袋の上部を輪ゴムで縛り、1時間放置して、吸水性樹脂を十分に膨潤させた。遠心力が167Gとなるよう設定した脱水機(国産遠心機株式会社製、品番:H−122)を用いて綿袋を1分間脱水し、脱水後の膨潤ゲルを含んだ綿袋の質量Wa(g)を測定した。吸水性樹脂を添加せずに同様の操作を行い、綿袋の湿潤時空質量Wb(g)を測定し、次式により保水能を求めた。
生理食塩水保水能(g/g)=[Wa−Wb](g)/吸水性樹脂の質量(g)
吸水性樹脂の2.07kPa荷重下での生理食塩水吸水能は、図1に機略構成を示した測定装置Xを用いて測定した。
荷重下での生理食塩水吸水能(mL/g)=Wc(mL)÷0.10(g)
500mL容のビーカーに、生理食塩水500±0.1gを量り取り、マグネチックスターラーバー(8mmφ×30mmのリング無し)を投入し、マグネチックスターラー(iuchi社製、品番:HS−30D)の上に配置した。引き続きマグネチックスターラーバーを600r/minで回転するように調整し、さらに、マグネチックスターラーバーの回転により生ずる渦の底部は、マグネチックスターラーバーの上部近くになるように調整した。
水可溶分(質量%)=〔[(Wd−We)×(500/80)]/2〕×100
JIS標準篩を上から、目開き850μmの篩、目開き600μmの篩、目開き425μmの篩、目開き300μmの篩、目開き150μmの篩、目開き75μmの篩および受け皿の順に組み合わせ、一番上の篩に吸水性樹脂約100gを入れ、ロータップ式振盪器を用いて、20分間振盪させた。
吸水性樹脂(吸水性樹脂前駆体)2.0gを、あらかじめ恒量(Wf(g))としたアルミホイールケース(8号)にとり精秤した(Wg(g))。上記サンプルを、内温を105℃に設定した熱風乾燥機(ADVANTEC社製)で2時間乾燥させた後、デシケーター中で放冷して、乾燥後の質量(Wh(g))を測定した。以下の式から、吸水性樹脂(吸水性樹脂前駆体)の乾燥減量(水分率)を算出した。
乾燥減量(水分率)(質量%)=[(Wg−Wf)−(Wh−Wf)]
÷(Wg−Wf)×100
温度計、撹拌機、還流冷却器、滴下ロートおよび窒素ガス導入管を備えた1リットル容の四つ口フラスコに、3−エチル−3−ヒドロキシメチルオキセタン44.1g(0.38モル)、トリエチルアミン44.6g(0.44モル)およびトルエン220gを仕込み、窒素ガス雰囲気下で内温が5℃になるまで、氷水浴で外部から冷却した。次いで、メタンスルホニルクロライド45.8g(0.4モル)を内温が10℃を超えないように滴下した後、室温に戻し、さらに2時間撹拌して反応させた。反応後、生成したトリエチルアミン塩酸塩をろ別し、少量のトルエンで洗浄し、反応ろ液を得た。この反応ろ液に、イオン交換水114gを添加、30分間攪拌した。反応液を分液ロートに移して分液した後、得られた有機層を、水浴温度85℃、減圧度75mmHgにて濃縮し、目的のメタンスルホン酸((3−エチルオキセタン−3−イル)メチル)を66.4g得た(0.34モル、収率:90%、純度85%)。なお、前記純度はガスクロマトグラフィーにより得られたチャートのピーク面積比より求めた。
温度計、撹拌機、還流冷却器、滴下ロートおよび窒素ガス導入管を備えた1リットル容の四つ口フラスコに、3−エチル−3−ヒドロキシメチルオキセタン44.1g(0.38モル)、トリエチルアミン44.6g(0.44モル)およびトルエン220gを仕込み、窒素ガス雰囲気下で内温が5℃になるまで、氷水浴で外部から冷却した。次いで、クロロメチルスルホニルクロライド59.6g(0.4モル)を内温が10℃を超えないように滴下した後、室温に戻し、さらに2時間撹拌して反応させた。反応後、生成したトリエチルアミン塩酸塩をろ別し、少量のトルエンで洗浄し、反応ろ液を得た。この反応ろ液に、イオン交換水114gを添加、30分間攪拌した。反応液を分液ロートに移して分液した後、得られた有機層を、水浴温度85℃、減圧度75mmHgにて濃縮し、目的のクロロメタンスルホン酸((3−エチルオキセタン−3−イル)メチル)を68.0g得た(0.30モル、収率:78%、純度74%)。なお、前記純度はガスクロマトグラフィーにより得られたチャートのピーク面積比より求めた。
還流冷却器、滴下ロート、窒素ガス導入管ならびに攪拌機および撹拌羽根を備えた内径110mm、2L容の丸底円筒型セパラブルフラスコを準備した。このフラスコにn−ヘプタン340gをとり、HLB3のショ糖ステアリン酸エステル(三菱化学フーズ(株)、リョートーシュガーエステルS−370)0.92gおよび無水マレイン酸変性エチレン・プロピレン共重合体(三井化学(株)、ハイワックス1105A)0.92gを添加し、撹拌しつつ80℃まで昇温して界面活性剤を溶解した後、50℃まで冷却した。
還流冷却器、滴下ロート、窒素ガス導入管ならびに攪拌機および撹拌羽根を備えた内径110mm、2L容の丸底円筒型セパラブルフラスコに、製造例1で得られた吸水性樹脂前駆体(A1)50g(前駆体を得るために使用した水溶性エチレン性不飽和単量体の理論量:0.52モル)およびn−ヘプタン80gを入れた。内温を80℃まで昇温した後、水8.0gを添加して同温度で10分間保持した(吸水性樹脂前駆体の水分率:19.9質量%)。
還流冷却器、滴下ロート、窒素ガス導入管ならびに攪拌機および撹拌羽根を備えた内径110mm、2L容の丸底円筒型セパラブルフラスコに、製造例1で得られた吸水性樹脂前駆体(A1)50g(前駆体を得るために使用した水溶性エチレン性不飽和単量体の理論量:0.52モル)およびn−ヘプタン80gを入れた。内温を80℃まで昇温した後、水8.0gを添加して同温度で10分間保持した(吸水性樹脂前駆体の水分率:19.9質量%)。
還流冷却器、滴下ロート、窒素ガス導入管ならびに攪拌機および撹拌羽根を備えた内径110mm、2L容の丸底円筒型セパラブルフラスコに、製造例1で得られた吸水性樹脂前駆体(A1)50g(前駆体を得るために使用した水溶性エチレン性不飽和単量体の理論量:0.52モル)およびn−ヘプタン80gを入れた。内温を80℃まで昇温した後、水3.5gを添加して同温度で10分間保持した(吸水性樹脂前駆体の水分率:13.2質量%)。
還流冷却器、滴下ロート、窒素ガス導入管ならびに攪拌機および撹拌羽根を備えた内径110mm、2L容の丸底円筒型セパラブルフラスコを準備した。このフラスコにn−ヘプタン340gをとり、HLB3のショ糖ステアリン酸エステル(三菱化学フーズ(株)、リョートーシュガーエステルS−370)0.92gおよび無水マレイン酸変性エチレン・プロピレン共重合体(三井化学(株)、ハイワックス1105A)0.92gを添加し、撹拌しつつ80℃まで昇温して界面活性剤を溶解した後、50℃まで冷却した。
製造例1で得られた吸水性樹脂前駆体(A1)について物性を上記の方法で測定し、結果を表1に示した。
還流冷却器、滴下ロート、窒素ガス導入管ならびに攪拌機および撹拌羽根を備えた内径110mm、2L容の丸底円筒型セパラブルフラスコに、製造例1で得られた吸水性樹脂前駆体(A1)50g(前駆体を得るために使用した水溶性エチレン性不飽和単量体の理論量:0.52モル)およびn−ヘプタン80gを入れた。
還流冷却器、滴下ロート、窒素ガス導入管ならびに攪拌機および撹拌羽根を備えた内径110mm、2L容の丸底円筒型セパラブルフラスコに、製造例1で得られた吸水性樹脂前駆体(A1)50g(前駆体を得るために使用した水溶性エチレン性不飽和単量体の理論量:0.52モル)およびn−ヘプタン80gを入れた。
還流冷却器、滴下ロート、窒素ガス導入管ならびに攪拌機および撹拌羽根を備えた内径110mm、2L容の丸底円筒型セパラブルフラスコに、製造例1で得られた吸水性樹脂前駆体(A1)50g(前駆体を得るために使用した水溶性エチレン性不飽和単量体の理論量:0.52モル)およびn−ヘプタン80gを入れた。
Claims (2)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2009538002A JP5558824B2 (ja) | 2007-10-24 | 2008-09-09 | 吸水性樹脂の製造方法 |
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2007275961 | 2007-10-24 | ||
JP2007275961 | 2007-10-24 | ||
JP2009538002A JP5558824B2 (ja) | 2007-10-24 | 2008-09-09 | 吸水性樹脂の製造方法 |
PCT/JP2008/066249 WO2009054197A1 (ja) | 2007-10-24 | 2008-09-09 | 吸水性樹脂の製造方法およびそれにより得られる吸水性樹脂 |
Publications (2)
Publication Number | Publication Date |
---|---|
JPWO2009054197A1 JPWO2009054197A1 (ja) | 2011-03-03 |
JP5558824B2 true JP5558824B2 (ja) | 2014-07-23 |
Family
ID=40579304
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2009538002A Active JP5558824B2 (ja) | 2007-10-24 | 2008-09-09 | 吸水性樹脂の製造方法 |
Country Status (7)
Country | Link |
---|---|
US (1) | US20100256308A1 (ja) |
EP (1) | EP2204388B1 (ja) |
JP (1) | JP5558824B2 (ja) |
KR (1) | KR101523799B1 (ja) |
CN (1) | CN101835814B (ja) |
ES (1) | ES2398736T3 (ja) |
WO (1) | WO2009054197A1 (ja) |
Families Citing this family (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US9221030B2 (en) | 2011-03-28 | 2015-12-29 | Sumitomo Seika Chemicals Co., Ltd. | Method for producing water-absorbent resin |
CN103764685B (zh) * | 2011-08-30 | 2015-12-02 | 住友精化株式会社 | 吸水性树脂的制造方法、以及由其得到的吸水性树脂 |
KR20140134219A (ko) | 2013-05-13 | 2014-11-21 | 주식회사 엘지화학 | 고흡수성 수지 및 이의 제조 방법 |
US11491463B2 (en) | 2018-01-09 | 2022-11-08 | Basf Se | Superabsorber mixtures |
JP7342035B2 (ja) | 2018-02-06 | 2023-09-11 | ビーエーエスエフ ソシエタス・ヨーロピア | 超吸収体粒子を空気輸送する方法 |
JPWO2020218163A1 (ja) * | 2019-04-23 | 2020-10-29 |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2002194239A (ja) * | 2000-10-20 | 2002-07-10 | Nippon Shokubai Co Ltd | 吸水剤、および吸水剤の製造方法 |
JP2003313446A (ja) * | 2002-04-18 | 2003-11-06 | Nippon Shokubai Co Ltd | 架橋構造を有する高吸水性樹脂を主成分とする吸水剤、およびその製造方法、並びにこれを用いた衛生材料 |
Family Cites Families (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP3434028B2 (ja) | 1994-07-20 | 2003-08-04 | 株式会社日本触媒 | 吸水性樹脂の改質方法、吸水剤および吸水性樹脂組成物 |
US6015864A (en) * | 1996-11-12 | 2000-01-18 | Akzo Nobel Nv | Thermosetting powder coating composition |
IL141849A0 (en) * | 1998-09-28 | 2002-03-10 | Carlsberg As | Peg-based macromonomers, chemically inert polymers prepared therefrom and the use of these polymers for organic synthesis and enzyme reactions |
EP0999238B1 (en) * | 1998-11-05 | 2008-07-09 | Nippon Shokubai Co., Ltd. | Water-absorbing agent and production process therefor |
JP4860019B2 (ja) | 1998-11-05 | 2012-01-25 | 株式会社日本触媒 | 吸水剤とその製造方法および用途 |
JP4168530B2 (ja) * | 1999-05-07 | 2008-10-22 | 宇部興産株式会社 | コーティング用紫外線硬化性組成物およびそれから得られるコーティング材ならびにその製造方法 |
US6809158B2 (en) * | 2000-10-20 | 2004-10-26 | Nippon Shokubai Co., Ltd. | Water-absorbing agent and process for producing the same |
US6753434B1 (en) * | 2003-05-06 | 2004-06-22 | National Starch And Chemical Investment Holding Corporation | Oxetane compounds containing cinnamyl functionality |
CN100436486C (zh) * | 2003-12-25 | 2008-11-26 | 住友精化株式会社 | 吸水性树脂的制备方法 |
AU2005285763A1 (en) * | 2004-09-24 | 2006-03-30 | Nippon Shokubai Co., Ltd. | Particulate water-absorbing agent containing water-absorbent resin as a main component |
JP5014607B2 (ja) * | 2004-09-24 | 2012-08-29 | 株式会社日本触媒 | 吸水性樹脂を主成分とする粒子状吸水剤 |
WO2006088115A1 (en) * | 2005-02-15 | 2006-08-24 | Nippon Shokubai Co., Ltd. | Water absorbing agent, water absorbing article and method for production of water absorbing agent |
JP4965865B2 (ja) * | 2005-02-15 | 2012-07-04 | 株式会社日本触媒 | 吸水剤、吸収性物品及び吸水剤の製造方法 |
JP2007099845A (ja) * | 2005-09-30 | 2007-04-19 | Procter & Gamble Co | 水性液吸収剤およびその製法 |
-
2008
- 2008-09-09 WO PCT/JP2008/066249 patent/WO2009054197A1/ja active Application Filing
- 2008-09-09 JP JP2009538002A patent/JP5558824B2/ja active Active
- 2008-09-09 CN CN200880112898.4A patent/CN101835814B/zh active Active
- 2008-09-09 ES ES08843156T patent/ES2398736T3/es active Active
- 2008-09-09 US US12/738,847 patent/US20100256308A1/en not_active Abandoned
- 2008-09-09 KR KR1020107010923A patent/KR101523799B1/ko active IP Right Grant
- 2008-09-09 EP EP08843156A patent/EP2204388B1/en active Active
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2002194239A (ja) * | 2000-10-20 | 2002-07-10 | Nippon Shokubai Co Ltd | 吸水剤、および吸水剤の製造方法 |
JP2003313446A (ja) * | 2002-04-18 | 2003-11-06 | Nippon Shokubai Co Ltd | 架橋構造を有する高吸水性樹脂を主成分とする吸水剤、およびその製造方法、並びにこれを用いた衛生材料 |
Also Published As
Publication number | Publication date |
---|---|
CN101835814B (zh) | 2015-09-09 |
EP2204388B1 (en) | 2012-11-21 |
US20100256308A1 (en) | 2010-10-07 |
KR20100087167A (ko) | 2010-08-03 |
JPWO2009054197A1 (ja) | 2011-03-03 |
ES2398736T3 (es) | 2013-03-21 |
KR101523799B1 (ko) | 2015-05-28 |
WO2009054197A1 (ja) | 2009-04-30 |
CN101835814A (zh) | 2010-09-15 |
EP2204388A4 (en) | 2010-11-03 |
EP2204388A1 (en) | 2010-07-07 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP5238502B2 (ja) | 吸水性樹脂の製造方法 | |
JP5099899B2 (ja) | 吸水性樹脂の製造方法 | |
JP5558824B2 (ja) | 吸水性樹脂の製造方法 | |
JP5719078B1 (ja) | 吸水性樹脂の製造方法 | |
JP5183918B2 (ja) | 吸水性樹脂の製造方法 | |
JP6567503B2 (ja) | 吸水性樹脂粒子の製造方法 | |
US8940845B2 (en) | Method for producing water-absorbing resin | |
JP6993878B2 (ja) | 吸水性樹脂および吸水剤 | |
TWI627189B (zh) | 吸水性樹脂粒子的製造方法 | |
JP4884009B2 (ja) | 吸水性樹脂の製造方法 | |
JP5191105B2 (ja) | 吸水性樹脂粒子の製造方法およびそれによって得られる吸水性樹脂粒子 | |
JPWO2004101628A1 (ja) | 吸水性樹脂の製造方法 | |
JP5336066B2 (ja) | 吸水性樹脂粒子の製造方法 | |
JP5551438B2 (ja) | 吸水性樹脂の製造方法およびそれにより得られる吸水性樹脂 | |
JPWO2005012369A1 (ja) | 吸水性樹脂の製造方法 | |
JP4976679B2 (ja) | 吸水性樹脂およびその製造方法 | |
WO2006068067A1 (ja) | 吸水性樹脂粒子の製造方法 | |
JP2002284805A (ja) | 高吸水性ポリマーの製造方法 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20110822 |
|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20110822 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20130902 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20131031 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20140528 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20140605 |
|
R150 | Certificate of patent or registration of utility model |
Ref document number: 5558824 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |