JP2021526582A - 高吸水性樹脂およびその製造方法 - Google Patents
高吸水性樹脂およびその製造方法 Download PDFInfo
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- JP2021526582A JP2021526582A JP2021518852A JP2021518852A JP2021526582A JP 2021526582 A JP2021526582 A JP 2021526582A JP 2021518852 A JP2021518852 A JP 2021518852A JP 2021518852 A JP2021518852 A JP 2021518852A JP 2021526582 A JP2021526582 A JP 2021526582A
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- JP
- Japan
- Prior art keywords
- absorbent resin
- highly water
- resilience value
- producing
- acrylic acid
- 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.)
- Granted
Links
- 229920005989 resin Polymers 0.000 title claims abstract description 137
- 239000011347 resin Substances 0.000 title claims abstract description 137
- 239000002250 absorbent Substances 0.000 title claims abstract description 107
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 29
- 238000010521 absorption reaction Methods 0.000 claims abstract description 36
- 229920000642 polymer Polymers 0.000 claims description 74
- 239000000178 monomer Substances 0.000 claims description 49
- 239000000017 hydrogel Substances 0.000 claims description 46
- 238000000034 method Methods 0.000 claims description 44
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 32
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 32
- 239000000843 powder Substances 0.000 claims description 32
- 238000004132 cross linking Methods 0.000 claims description 24
- 239000003431 cross linking reagent Substances 0.000 claims description 23
- 238000010298 pulverizing process Methods 0.000 claims description 23
- 239000000203 mixture Substances 0.000 claims description 22
- 238000001035 drying Methods 0.000 claims description 20
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 16
- -1 alkyl-aryl ether phosphate Chemical class 0.000 claims description 16
- 239000004088 foaming agent Substances 0.000 claims description 16
- 230000008569 process Effects 0.000 claims description 15
- 238000011084 recovery Methods 0.000 claims description 15
- 239000004094 surface-active agent Substances 0.000 claims description 15
- 239000003505 polymerization initiator Substances 0.000 claims description 14
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 12
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 12
- 229920001577 copolymer Polymers 0.000 claims description 12
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 12
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 8
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 claims description 6
- 230000002378 acidificating effect Effects 0.000 claims description 6
- 239000002504 physiological saline solution Substances 0.000 claims description 6
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 6
- 235000011181 potassium carbonates Nutrition 0.000 claims description 6
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims description 6
- 235000017557 sodium bicarbonate Nutrition 0.000 claims description 6
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 6
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 5
- 230000000379 polymerizing effect Effects 0.000 claims description 5
- 230000008961 swelling Effects 0.000 claims description 5
- 229910019142 PO4 Inorganic materials 0.000 claims description 4
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 claims description 4
- 239000010452 phosphate Substances 0.000 claims description 4
- 239000011780 sodium chloride Substances 0.000 claims description 4
- 229910000019 calcium carbonate Inorganic materials 0.000 claims description 3
- 238000011068 loading method Methods 0.000 claims description 3
- 239000011734 sodium Substances 0.000 claims description 3
- JGTNAGYHADQMCM-UHFFFAOYSA-M 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F JGTNAGYHADQMCM-UHFFFAOYSA-M 0.000 claims description 2
- YFSUTJLHUFNCNZ-UHFFFAOYSA-M 1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-heptadecafluorooctane-1-sulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F YFSUTJLHUFNCNZ-UHFFFAOYSA-M 0.000 claims description 2
- 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 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 2
- BTBJBAZGXNKLQC-UHFFFAOYSA-N ammonium lauryl sulfate Chemical compound [NH4+].CCCCCCCCCCCCOS([O-])(=O)=O BTBJBAZGXNKLQC-UHFFFAOYSA-N 0.000 claims description 2
- 229940063953 ammonium lauryl sulfate Drugs 0.000 claims description 2
- NKWPZUCBCARRDP-UHFFFAOYSA-L calcium bicarbonate Chemical compound [Ca+2].OC([O-])=O.OC([O-])=O NKWPZUCBCARRDP-UHFFFAOYSA-L 0.000 claims description 2
- 229910000020 calcium bicarbonate Inorganic materials 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 235000019329 dioctyl sodium sulphosuccinate Nutrition 0.000 claims description 2
- YHAIUSTWZPMYGG-UHFFFAOYSA-L disodium;2,2-dioctyl-3-sulfobutanedioate Chemical compound [Na+].[Na+].CCCCCCCCC(C([O-])=O)(C(C([O-])=O)S(O)(=O)=O)CCCCCCCC YHAIUSTWZPMYGG-UHFFFAOYSA-L 0.000 claims description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 2
- QWDJLDTYWNBUKE-UHFFFAOYSA-L magnesium bicarbonate Chemical compound [Mg+2].OC([O-])=O.OC([O-])=O QWDJLDTYWNBUKE-UHFFFAOYSA-L 0.000 claims description 2
- 239000002370 magnesium bicarbonate Substances 0.000 claims description 2
- 229910000022 magnesium bicarbonate Inorganic materials 0.000 claims description 2
- 235000014824 magnesium bicarbonate Nutrition 0.000 claims description 2
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 claims description 2
- 239000001095 magnesium carbonate Substances 0.000 claims description 2
- 229910000021 magnesium carbonate Inorganic materials 0.000 claims description 2
- 235000015497 potassium bicarbonate Nutrition 0.000 claims description 2
- 229910000028 potassium bicarbonate Inorganic materials 0.000 claims description 2
- 239000011736 potassium bicarbonate Substances 0.000 claims description 2
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 claims description 2
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- 229940083575 sodium dodecyl sulfate Drugs 0.000 claims description 2
- 229940057950 sodium laureth sulfate Drugs 0.000 claims description 2
- SXHLENDCVBIJFO-UHFFFAOYSA-M sodium;2-[2-(2-dodecoxyethoxy)ethoxy]ethyl sulfate Chemical compound [Na+].CCCCCCCCCCCCOCCOCCOCCOS([O-])(=O)=O SXHLENDCVBIJFO-UHFFFAOYSA-M 0.000 claims description 2
- 239000000243 solution Substances 0.000 description 28
- 239000002245 particle Substances 0.000 description 25
- 238000006116 polymerization reaction Methods 0.000 description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
- 239000002585 base Substances 0.000 description 20
- 239000000499 gel Substances 0.000 description 20
- 230000000052 comparative effect Effects 0.000 description 17
- 239000011259 mixed solution Substances 0.000 description 16
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 15
- 230000000704 physical effect Effects 0.000 description 15
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 13
- 238000006243 chemical reaction Methods 0.000 description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 12
- 239000007788 liquid Substances 0.000 description 11
- 239000003999 initiator Substances 0.000 description 10
- 238000006386 neutralization reaction Methods 0.000 description 10
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 9
- 239000000463 material Substances 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 238000012719 thermal polymerization Methods 0.000 description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Natural products CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 7
- 238000005187 foaming Methods 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000011521 glass Substances 0.000 description 6
- 229920001223 polyethylene glycol Polymers 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 239000002202 Polyethylene glycol Substances 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- XLLIQLLCWZCATF-UHFFFAOYSA-N 2-methoxyethyl acetate Chemical compound COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 4
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 4
- 229910002016 Aerosil® 200 Inorganic materials 0.000 description 4
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 description 4
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 4
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 4
- 235000011187 glycerol Nutrition 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 239000011148 porous material Substances 0.000 description 4
- 235000011121 sodium hydroxide Nutrition 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 229920000247 superabsorbent polymer Polymers 0.000 description 4
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 239000003945 anionic surfactant Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 230000018109 developmental process Effects 0.000 description 3
- 125000004386 diacrylate group Chemical group 0.000 description 3
- 238000010586 diagram Methods 0.000 description 3
- 230000006872 improvement Effects 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 239000002736 nonionic surfactant Substances 0.000 description 3
- 229920001451 polypropylene glycol Polymers 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- ZORQXIQZAOLNGE-UHFFFAOYSA-N 1,1-difluorocyclohexane Polymers FC1(F)CCCCC1 ZORQXIQZAOLNGE-UHFFFAOYSA-N 0.000 description 2
- UWFRVQVNYNPBEF-UHFFFAOYSA-N 1-(2,4-dimethylphenyl)propan-1-one Chemical compound CCC(=O)C1=CC=C(C)C=C1C UWFRVQVNYNPBEF-UHFFFAOYSA-N 0.000 description 2
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-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
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 2
- AOBIOSPNXBMOAT-UHFFFAOYSA-N 2-[2-(oxiran-2-ylmethoxy)ethoxymethyl]oxirane Chemical compound C1OC1COCCOCC1CO1 AOBIOSPNXBMOAT-UHFFFAOYSA-N 0.000 description 2
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 2
- AMIJXNFLZXFHJA-UHFFFAOYSA-N 2-dimethylphosphoryl-1-(2,4,6-trimethylphenyl)ethanone Chemical compound CC1=C(C(=O)CP(C)(C)=O)C(=CC(=C1)C)C AMIJXNFLZXFHJA-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
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- NWGKJDSIEKMTRX-AAZCQSIUSA-N Sorbitan monooleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O NWGKJDSIEKMTRX-AAZCQSIUSA-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
- 230000002745 absorbent Effects 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 229910001870 ammonium persulfate Inorganic materials 0.000 description 2
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 2
- 229930188620 butyrolactone Natural products 0.000 description 2
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 2
- 238000007865 diluting Methods 0.000 description 2
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- 238000009826 distribution Methods 0.000 description 2
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- 238000010438 heat treatment Methods 0.000 description 2
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 2
- 230000035699 permeability Effects 0.000 description 2
- JRKICGRDRMAZLK-UHFFFAOYSA-L peroxydisulfate Chemical compound [O-]S(=O)(=O)OOS([O-])(=O)=O JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 2
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 2
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
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- CHQMHPLRPQMAMX-UHFFFAOYSA-L sodium persulfate Substances [Na+].[Na+].[O-]S(=O)(=O)OOS([O-])(=O)=O CHQMHPLRPQMAMX-UHFFFAOYSA-L 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
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- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 1
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 description 1
- MYWOJODOMFBVCB-UHFFFAOYSA-N 1,2,6-trimethylphenanthrene Chemical compound CC1=CC=C2C3=CC(C)=CC=C3C=CC2=C1C MYWOJODOMFBVCB-UHFFFAOYSA-N 0.000 description 1
- AZCYBBHXCQYWTO-UHFFFAOYSA-N 2-[(2-chloro-6-fluorophenyl)methoxy]benzaldehyde Chemical compound FC1=CC=CC(Cl)=C1COC1=CC=CC=C1C=O AZCYBBHXCQYWTO-UHFFFAOYSA-N 0.000 description 1
- HDPLHDGYGLENEI-UHFFFAOYSA-N 2-[1-(oxiran-2-ylmethoxy)propan-2-yloxymethyl]oxirane Chemical compound C1OC1COC(C)COCC1CO1 HDPLHDGYGLENEI-UHFFFAOYSA-N 0.000 description 1
- LCZVSXRMYJUNFX-UHFFFAOYSA-N 2-[2-(2-hydroxypropoxy)propoxy]propan-1-ol Chemical compound CC(O)COC(C)COC(C)CO LCZVSXRMYJUNFX-UHFFFAOYSA-N 0.000 description 1
- FDSUVTROAWLVJA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol;prop-2-enoic acid Chemical compound OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OCC(CO)(CO)COCC(CO)(CO)CO FDSUVTROAWLVJA-UHFFFAOYSA-N 0.000 description 1
- CKSAKVMRQYOFBC-UHFFFAOYSA-N 2-cyanopropan-2-yliminourea Chemical compound N#CC(C)(C)N=NC(N)=O CKSAKVMRQYOFBC-UHFFFAOYSA-N 0.000 description 1
- CFYOKDXIYDYSPV-UHFFFAOYSA-N 2-ethyl-2-(hydroxymethyl)propane-1,3-diol;hexane-1,1-diol Chemical compound CCCCCC(O)O.CCC(CO)(CO)CO CFYOKDXIYDYSPV-UHFFFAOYSA-N 0.000 description 1
- NLGDWWCZQDIASO-UHFFFAOYSA-N 2-hydroxy-1-(7-oxabicyclo[4.1.0]hepta-1,3,5-trien-2-yl)-2-phenylethanone Chemical compound OC(C(=O)c1cccc2Oc12)c1ccccc1 NLGDWWCZQDIASO-UHFFFAOYSA-N 0.000 description 1
- SMBRHGJEDJVDOB-UHFFFAOYSA-N 2-methylpropanimidamide;dihydrochloride Chemical compound Cl.Cl.CC(C)C(N)=N SMBRHGJEDJVDOB-UHFFFAOYSA-N 0.000 description 1
- BPAZNZINLQSFMN-UHFFFAOYSA-N 2-propan-2-yl-4,5-dihydro-1h-imidazole;dihydrochloride Chemical compound Cl.Cl.CC(C)C1=NCCN1 BPAZNZINLQSFMN-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Natural products OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- 244000025254 Cannabis sativa Species 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 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 1
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- Compositions Of Macromolecular Compounds (AREA)
Abstract
Description
本出願は、2019年1月17日付韓国特許出願第10−2019−0006228号および2020年1月16日付韓国特許出願第10−2020−0006215号に基づいた優先権の利益を主張し、当該韓国特許出願の文献に開示された全ての内容は本明細書の一部として組み含まれる。
下記式1で計算される高吸水性樹脂の回復率(Recovery rate)が85%以上である、高吸水性樹脂を提供する:
回復率(%)=4次レジリエンス値(resilience value)/1次レジリエンス値(resilience value)×100
1次レジリエンス値は、高吸水性樹脂2gを無加圧下で1時間生理食塩水(0.9wt% NaCl)200mLに膨潤させた後、DMA(Dynamic mechanical analysis)測定装置にローディングして常温(25℃)および0.72psi下で5分間加圧した後、加圧を解除して10分間定置させた後に測定される高吸水性樹脂のモジュラス(modulus、単位:kPa)であり、
4次レジリエンス値は、前記1次レジリエンス値を測定した後、再び加圧してレジリエンス値を測定する過程を同一にさらに3回繰り返して4回目に測定される高吸水性樹脂のモジュラス(modulus、単位:kPa)である。
少なくとも一部が中和された酸性基を有するアクリル酸系単量体、発泡剤、内部架橋剤および重合開始剤を含む単量体組成物を重合して含水ゲル重合体を形成する段階;
前記含水ゲル重合体を、直列に配列された2個以上のホールプレート(hole plate)を含むチョッパー(chopper)を通過させてチョッピングする段階;
前記チョッピングした含水ゲル重合体を乾燥、粉砕および分級してベース樹脂を形成する段階;および
表面架橋剤の存在下で、前記ベース樹脂粉末の表面を追加架橋して表面架橋層を形成する段階;
を含む、高吸水性樹脂の製造方法を提供する。
回復率(%)=4次レジリエンス値(resilience value)/1次レジリエンス値(resilience value)×100
1次レジリエンス値は、高吸水性樹脂2gを無加圧下で1時間生理食塩水(0.9wt% NaCl)200mLに膨潤させた後、DMA(Dynamic mechanical analysis)測定装置にローディングして常温(25℃)および0.72psi下で5分間加圧した後、加圧を解除して10分間定置させた後に測定される高吸水性樹脂のモジュラス(modulus、単位:kPa)であり、
4次レジリエンス値は、前記1次レジリエンス値を測定した後、再び加圧してレジリエンス値を測定する過程を同一にさらに3回繰り返して4回目に測定される高吸水性樹脂のモジュラス(modulus、単位:kPa)である。
R1−COOM1
R1は不飽和結合を含む炭素数2乃至5のアルキル基であり、
M1は水素原子、1価または2価金属、アンモニウム基または有機アミン塩である。
実施例1
アクリル酸に0.5重量%に希釈されたIRGACURE819開始剤8.6g(単量体に対して80ppmw)とアクリル酸に20重量%に希釈されたポリエチレングリコールジアクリレート(PEGDA、Mw=400)12.3gを混合した溶液(A溶液)を製造した。
実施例1で、ホールプレート3個を含むチョッパー(各ホールプレートのホールの平均直径は順に18mm、14mm、12mm)を利用したことを除き、実施例1と同様な方法で高吸水性樹脂を製造した。
実施例1で、C溶液に界面活性剤としてドデシル硫酸ナトリウム(sodium dodecylsulfate)を前記アクリル酸の総重量に対して100ppmwになるように追加したことを除き、実施例1と同様の方法で高吸水性樹脂を製造した。
実施例2で、C溶液に界面活性剤としてドデシル硫酸ナトリウム(sodium dodecylsulfate)を前記アクリル酸の総重量に対して100ppmwになるように追加したことを除き、実施例2と同様の方法で高吸水性樹脂を製造した。
アクリル酸に0.5重量%に希釈されたIRGACURE819開始剤8.6g(単量体に対して80ppmw)とアクリル酸に20重量%に希釈されたポリエチレングリコールジアクリレート(PEGDA、Mw=400)12.3gを混合した溶液(A溶液)を製造した。
アクリル酸に0.5重量%に希釈されたIRGACURE819開始剤8.6g(単量体に対して80ppmw)とアクリル酸に20重量%に希釈されたポリエチレングリコールジアクリレート(PEGDA、Mw=400)12.3gを混合した溶液(A溶液)を製造した。
比較例2のチョッピング段階で、図3に示されたようなチョッパー(並列に連結された2個のチョッパー、各チョッパーのホールプレートのホールの平均直径は順に18mm、14mm)を利用してチョッピングすることによって前記裁断されたシートを粉(crumb)で製造した。製造された粉(crumb)の平均粒子大きさ(直径)は0.4mmであった。
比較例2のチョッピング段階で、図3に示されたものと類似する並列チョッパー(ただし、並列に連結された3個のチョッパー、各チョッパーのホールプレートのホールの平均直径は順に18mm、14mm、12mm)を利用してチョッピングすることによって前記裁断されたシートを粉(crumb)で製造した。製造された粉(crumb)の平均粒子大きさ(直径)は0.3mmであった。
比較例1のチョッピング段階で、図1に示されたものと類似するチョッパー(ただし、ホールプレート2個を含み、各ホールプレートのホールの平均直径は順に14mm、12mm)を利用してチョッピングすることによって前記裁断されたシートを粉(crumb)で製造した。製造された粉(crumb)の平均粒子大きさ(直径)は0.3mmであった。
韓国公開特許出願第2018−0076272号の実施例2により高吸水性樹脂を製造した。
前記実施例および比較例で製造した高吸水性樹脂の物性を以下の方法で評価し、その結果を表1に示した。
高吸水性樹脂2gを無加圧下で1時間生理食塩水(0.9wt% NaCl)200mLに膨潤させた後、DMA(Dynamic mechanical analysis)測定装置(機器名:Dynamic mechanical analysisQ800、製造会社:TA instrument)にローディングして常温(25℃)および0.72psi下で5分間加圧した後、加圧を解除して10分間定置させた後、高吸水性樹脂のモジュラス(modulus、単位:kPa)を測定して1次レジリエンス値を求めた。
回復率(%)=4次レジリエンス値(resilience value)/1次レジリエンス値(resilience value)×100
実施例および比較例の高吸水性樹脂の吸収速度は、国際公開第1987/003208号に記載された方法に準じて秒単位で測定された。
Claims (11)
- 下記式1で計算される高吸水性樹脂の回復率(Recovery rate)が85%以上である、高吸水性樹脂:
[式1]
回復率(%)=4次レジリエンス値(resilience value)/1次レジリエンス値(resilience value)×100
式1で、
1次レジリエンス値は、高吸水性樹脂2gを無加圧下で1時間生理食塩水(0.9wt% NaCl)200mLに膨潤させた後、DMA(Dynamic mechanical analysis)測定装置にローディングして常温(25℃)および0.72psi下で5分間加圧した後、加圧を解除して10分間定置させた後に測定される高吸水性樹脂のモジュラス(modulus、単位:kPa)であり、
4次レジリエンス値は、前記1次レジリエンス値を測定した後、再び加圧してレジリエンス値を測定する過程を同一にさらに3回繰り返して4回目に測定される高吸水性樹脂のモジュラス(modulus、単位:kPa)である。 - 前記1次レジリエンス値が90kPa以上である、請求項1に記載の高吸水性樹脂。
- ボルテックス(vortex)測定方法により測定した吸収速度が40秒以下である、請求項1または2に記載の高吸水性樹脂。
- 少なくとも一部が中和された酸性基を有するアクリル酸系単量体、発泡剤、内部架橋剤および重合開始剤を含む単量体組成物を重合して含水ゲル重合体を形成する段階;
前記含水ゲル重合体を、直列に配列された2個以上のホールプレート(hole plate)を含むチョッパー(chopper)を通過させてチョッピングする段階;
前記チョッピングした含水ゲル重合体を乾燥、粉砕および分級してベース樹脂を形成する段階;および
表面架橋剤の存在下で、前記ベース樹脂粉末の表面を追加架橋して表面架橋層を形成する段階
を含む、高吸水性樹脂の製造方法。 - 前記ホールプレートの平均直径は、チョッパー入口から遠くなるほどより小さい、請求項4に記載の高吸水性樹脂の製造方法。
- 前記発泡剤は、重炭酸ナトリウム(sodium bicarbonate)、炭酸ナトリウム(sodium carbonate)、重炭酸カリウム(potassium bicarbonate)、炭酸カリウム(potassium carbonate)、重炭酸カルシウム(calcium bicarbonate)、炭酸カルシウム(calcium carbonate)、重炭酸マグネシウム(magnesium bicarbonate)および炭酸マグネシウム(magnesium carbonate)からなる群より選択された1種以上を含む、請求項4または5に記載の高吸水性樹脂の製造方法。
- 前記発泡剤は、前記アクリル酸単量体の総重量に対して500ppmw以下で含まれる、請求項4から6のいずれか一項に記載の高吸水性樹脂の製造方法。
- 前記単量体組成物は、界面活性剤をさらに含む、請求項4から7のいずれか一項に記載の高吸水性樹脂の製造方法。
- 前記界面活性剤は、ドデシル硫酸ナトリウム、ラウリル硫酸アンモニウム、ラウレス硫酸ナトリウム、スルホコハク酸ジオクチルナトリウム、ペルフルオロオクタンスルホネート、ペルフルオロブタンスルホネート、アルキル−アリールエーテルホスフェート、アルキルエーテルホスフェート、ミレス硫酸ナトリウムおよびカルボキシレート塩からなる群より選択された1種以上を含む、請求項8に記載の高吸水性樹脂の製造方法。
- 前記チョッピングする段階で、ポリカルボン酸系共重合体をさらに投入してチョッピングする、請求項4から9のいずれか一項に記載の高吸水性樹脂の製造方法。
- 前記ポリカルボン酸系共重合体は、アルコキシポリアルキレングリコールモノ(メタ)アクリル酸エステル系単量体および(メタ)アクリル酸エステル系単量体からなる群より選択された1種以上を含む、請求項10に記載の高吸水性樹脂の製造方法。
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