WO2018139768A1 - 고흡수성 수지의 제조 방법 - Google Patents
고흡수성 수지의 제조 방법 Download PDFInfo
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- WO2018139768A1 WO2018139768A1 PCT/KR2017/015485 KR2017015485W WO2018139768A1 WO 2018139768 A1 WO2018139768 A1 WO 2018139768A1 KR 2017015485 W KR2017015485 W KR 2017015485W WO 2018139768 A1 WO2018139768 A1 WO 2018139768A1
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- Prior art keywords
- meth
- polymer
- acrylate
- particles
- glycol
- Prior art date
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- 229920000247 superabsorbent polymer Polymers 0.000 title claims abstract description 71
- 238000000034 method Methods 0.000 title claims abstract description 55
- 238000010521 absorption reaction Methods 0.000 claims abstract description 33
- 239000002245 particle Substances 0.000 claims description 111
- 229920000642 polymer Polymers 0.000 claims description 98
- 239000000017 hydrogel Substances 0.000 claims description 64
- 239000000178 monomer Substances 0.000 claims description 51
- 239000003431 cross linking reagent Substances 0.000 claims description 45
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 40
- 239000011347 resin Substances 0.000 claims description 30
- 229920005989 resin Polymers 0.000 claims description 30
- 238000000227 grinding Methods 0.000 claims description 28
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 26
- 238000001035 drying Methods 0.000 claims description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 22
- 239000000203 mixture Substances 0.000 claims description 20
- 230000008569 process Effects 0.000 claims description 19
- 238000004519 manufacturing process Methods 0.000 claims description 17
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 15
- 238000005187 foaming Methods 0.000 claims description 14
- 239000004604 Blowing Agent Substances 0.000 claims description 13
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 13
- -1 nucleic acid diol Chemical class 0.000 claims description 13
- 239000011780 sodium chloride Substances 0.000 claims description 13
- 239000000243 solution Substances 0.000 claims description 12
- 239000007864 aqueous solution Substances 0.000 claims description 11
- 239000000499 gel Substances 0.000 claims description 11
- 239000002250 absorbent Substances 0.000 claims description 10
- 239000002504 physiological saline solution Substances 0.000 claims description 10
- 238000010298 pulverizing process Methods 0.000 claims description 10
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 9
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 9
- 238000004364 calculation method Methods 0.000 claims description 8
- 229920006037 cross link polymer Polymers 0.000 claims description 8
- 239000011148 porous material Substances 0.000 claims description 8
- 230000002745 absorbent Effects 0.000 claims description 7
- 229920001223 polyethylene glycol Polymers 0.000 claims description 7
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 claims description 6
- 239000007787 solid Substances 0.000 claims description 6
- MWRWFPQBGSZWNV-UHFFFAOYSA-N Dinitrosopentamethylenetetramine Chemical compound C1N2CN(N=O)CN1CN(N=O)C2 MWRWFPQBGSZWNV-UHFFFAOYSA-N 0.000 claims description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 5
- 239000002202 Polyethylene glycol Substances 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 4
- NBOCQTNZUPTTEI-UHFFFAOYSA-N 4-[4-(hydrazinesulfonyl)phenoxy]benzenesulfonohydrazide Chemical compound C1=CC(S(=O)(=O)NN)=CC=C1OC1=CC=C(S(=O)(=O)NN)C=C1 NBOCQTNZUPTTEI-UHFFFAOYSA-N 0.000 claims description 4
- ICGLPKIVTVWCFT-UHFFFAOYSA-N 4-methylbenzenesulfonohydrazide Chemical compound CC1=CC=C(S(=O)(=O)NN)C=C1 ICGLPKIVTVWCFT-UHFFFAOYSA-N 0.000 claims description 4
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 4
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 claims description 4
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 4
- GCSPRLPXTPMSTL-IBDNADADSA-N [(2s,3r,4s,5s,6r)-2-[(2s,3s,4s,5r)-3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[C@@]1([C@]2(CO)[C@H]([C@H](O)[C@@H](CO)O2)O)O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O GCSPRLPXTPMSTL-IBDNADADSA-N 0.000 claims description 4
- HNRMPXKDFBEGFZ-UHFFFAOYSA-N ethyl trimethyl methane Natural products CCC(C)(C)C HNRMPXKDFBEGFZ-UHFFFAOYSA-N 0.000 claims description 4
- 235000011187 glycerol Nutrition 0.000 claims description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 239000004156 Azodicarbonamide Substances 0.000 claims description 3
- ZPVGIKNDGJGLCO-VGAMQAOUSA-N [(2s,3r,4s,5s,6r)-2-[(2s,3s,4s,5r)-3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] hexadecanoate Chemical compound CCCCCCCCCCCCCCCC(=O)O[C@@]1([C@]2(CO)[C@H]([C@H](O)[C@@H](CO)O2)O)O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O ZPVGIKNDGJGLCO-VGAMQAOUSA-N 0.000 claims description 3
- XOZUGNYVDXMRKW-AATRIKPKSA-N azodicarbonamide Chemical compound NC(=O)\N=N\C(N)=O XOZUGNYVDXMRKW-AATRIKPKSA-N 0.000 claims description 3
- 235000019399 azodicarbonamide Nutrition 0.000 claims description 3
- NKWPZUCBCARRDP-UHFFFAOYSA-L calcium bicarbonate Chemical compound [Ca+2].OC([O-])=O.OC([O-])=O NKWPZUCBCARRDP-UHFFFAOYSA-L 0.000 claims description 3
- 229910000019 calcium carbonate Inorganic materials 0.000 claims description 3
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 claims description 3
- 239000001095 magnesium carbonate Substances 0.000 claims description 3
- 229910000021 magnesium carbonate Inorganic materials 0.000 claims description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 claims 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 claims description 2
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 claims description 2
- 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 claims description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 2
- 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 claims description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
- MJIFFWRTVONWNO-UHFFFAOYSA-N 3-oxopent-4-ene-1-sulfonic acid Chemical compound OS(=O)(=O)CCC(=O)C=C MJIFFWRTVONWNO-UHFFFAOYSA-N 0.000 claims description 2
- SVYPQURSUBDSIQ-UHFFFAOYSA-N 4-methyl-3-oxopent-4-ene-1-sulfonic acid Chemical compound CC(=C)C(=O)CCS(O)(=O)=O SVYPQURSUBDSIQ-UHFFFAOYSA-N 0.000 claims description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 2
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 claims 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 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 claims description 2
- 229910000020 calcium bicarbonate Inorganic materials 0.000 claims description 2
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 claims description 2
- 239000001530 fumaric acid Substances 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
- 229910000022 magnesium bicarbonate Inorganic materials 0.000 claims description 2
- 239000002370 magnesium bicarbonate Substances 0.000 claims description 2
- 235000014824 magnesium bicarbonate Nutrition 0.000 claims description 2
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 2
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 claims description 2
- 102000039446 nucleic acids Human genes 0.000 claims description 2
- 108020004707 nucleic acids Proteins 0.000 claims description 2
- 229920001451 polypropylene glycol Polymers 0.000 claims description 2
- 239000011736 potassium bicarbonate Substances 0.000 claims description 2
- 235000015497 potassium bicarbonate Nutrition 0.000 claims description 2
- 229910000028 potassium bicarbonate Inorganic materials 0.000 claims description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 2
- 235000011181 potassium carbonates Nutrition 0.000 claims description 2
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 claims description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 2
- 235000017550 sodium carbonate Nutrition 0.000 claims description 2
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 claims description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 2
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 claims description 2
- VPYJNCGUESNPMV-UHFFFAOYSA-N triallylamine Chemical compound C=CCN(CC=C)CC=C VPYJNCGUESNPMV-UHFFFAOYSA-N 0.000 claims description 2
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 claims description 2
- 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 claims 1
- KCXFHTAICRTXLI-UHFFFAOYSA-N propane-1-sulfonic acid Chemical compound CCCS(O)(=O)=O KCXFHTAICRTXLI-UHFFFAOYSA-N 0.000 claims 1
- 230000035699 permeability Effects 0.000 abstract description 10
- 238000006116 polymerization reaction Methods 0.000 description 19
- 238000004132 cross linking Methods 0.000 description 17
- 230000000704 physical effect Effects 0.000 description 16
- 239000003505 polymerization initiator Substances 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 10
- 230000000052 comparative effect Effects 0.000 description 10
- 230000004048 modification Effects 0.000 description 10
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- 239000000843 powder Substances 0.000 description 10
- 239000003999 initiator Substances 0.000 description 8
- 239000004583 superabsorbent polymers (SAPs) Substances 0.000 description 8
- 239000007788 liquid Substances 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000000463 material Substances 0.000 description 5
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- 239000004745 nonwoven fabric Substances 0.000 description 5
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- 238000012719 thermal polymerization Methods 0.000 description 5
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 230000002378 acidificating effect Effects 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000004386 diacrylate group Chemical group 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
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- 238000010438 heat treatment Methods 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 230000000877 morphologic effect Effects 0.000 description 3
- JRKICGRDRMAZLK-UHFFFAOYSA-L peroxydisulfate Chemical compound [O-]S(=O)(=O)OOS([O-])(=O)=O JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 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
- 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 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
- SMBRHGJEDJVDOB-UHFFFAOYSA-N 2-methylpropanimidamide;dihydrochloride Chemical compound Cl.Cl.CC(C)C(N)=N SMBRHGJEDJVDOB-UHFFFAOYSA-N 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-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
- 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
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 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
- 150000007513 acids Chemical class 0.000 description 2
- 238000004220 aggregation Methods 0.000 description 2
- 230000002776 aggregation Effects 0.000 description 2
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
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- 238000007796 conventional method Methods 0.000 description 2
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- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 2
- 238000011161 development Methods 0.000 description 2
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- 150000002009 diols Chemical class 0.000 description 2
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- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 2
- 239000002994 raw material Substances 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
- 239000000126 substance Substances 0.000 description 2
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 1
- PUFAFJLYWMNNEC-UHFFFAOYSA-N 2-[2-(2-hydroxyethoxy)ethoxy]ethanol;prop-2-enoic acid Chemical compound OC(=O)C=C.OCCOCCOCCO PUFAFJLYWMNNEC-UHFFFAOYSA-N 0.000 description 1
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-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
- 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
- AEYSASDBPHWTGR-UHFFFAOYSA-N 4-oxohex-5-ene-3-sulfonic acid Chemical compound CCC(S(O)(=O)=O)C(=O)C=C AEYSASDBPHWTGR-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
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- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
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- PODOEQVNFJSWIK-UHFFFAOYSA-N diphenylphosphoryl-(2,4,6-trimethoxyphenyl)methanone Chemical compound COC1=CC(OC)=CC(OC)=C1C(=O)P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 PODOEQVNFJSWIK-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C08J9/10—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent by a chemical blowing agent developing nitrogen, the blowing agent being a compound containing a nitrogen-to-nitrogen bond
- C08J9/104—Hydrazines; Hydrazides; Semicarbazides; Semicarbazones; Hydrazones; Derivatives thereof
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
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- C08F2/10—Aqueous solvent
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
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- C08F2800/20—Copolymer characterised by the proportions of the comonomers expressed as weight or mass percentages
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- C08J2205/022—Hydrogel, i.e. a gel containing an aqueous composition
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- C08J2300/00—Characterised by the use of unspecified polymers
- C08J2300/14—Water soluble or water swellable polymers, e.g. aqueous gels
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- C08J2333/04—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 esters
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- C08J2333/06—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 esters of esters containing only carbon, hydrogen, and oxygen, the oxygen atom being present only as part of the carboxyl radical
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- C08J3/24—Crosslinking, e.g. vulcanising, of macromolecules
Definitions
- the present invention relates to a method for producing a super absorbent polymer.
- Super absorbent polymer is a synthetic polymer material that can absorb about 500 to 1000 times its own weight. It is a super absorbency material (SAM) and an absorbent gel material (AGM). ⁇ "Li ⁇ have c.
- Super absorbent polymers have been put into practical use as sanitary devices, and are now widely used in various fields such as hygiene products such as baby diapers, horticultural soil repair agents, civil engineering index materials, seedling sheets, and freshness retainers in food distribution. .
- these superabsorbent polymers are widely used in the field of sanitary products such as diapers and sanitary napkins.
- it is necessary to exhibit high absorption of moisture, and the absorbed moisture must not escape the external pressure.
- it is necessary to maintain good shape even in the state of absorbing water and expanding in volume (swelling), thereby showing excellent permeability.
- the proportion of the absorbent resin in the diaper tends to increase.
- the absorbent resin to combine the performance of the diaper's fiber material, and for this purpose, the absorbent resin must have a high absorption rate and high liquid absorption rate.
- the manufacturing process of the water absorbent resin generally a process of pulverizing a hydrous gel produced by polymerizing monomers of the water absorbent resin is required. Grinding of the hydrous gel is a necessary process for preparing the superabsorbent polymer in the form of powder or particles, which has a great influence on the properties of the superabsorbent polymer.
- Various studies have been conducted on this, and Japanese Patent Registration No.
- 3415036 discloses a manufacturing method of minimizing damage to hydrous gel during hydrogel grinding in order to reduce water-soluble components causing a decrease in absorption magnification.
- a high absorption magnification is possible by the above method, it is insufficient to obtain a level of absorption rate required for a recent diaper.
- Japanese Patent Registration No. 4866733 uses 0.2 mol% or more of an internal crosslinking agent to improve the fluid permeability and absorption rate of superabsorbent polymers, and the pore diameter of the porous plate of the screw extruder during hydrogel grinding. A method of controlling is disclosed.
- the present invention is to provide a method capable of producing a superabsorbent polymer having excellent absorption magnification, absorption rate and liquid permeability, and excellent in various physical properties required for the superabsorbent polymer.
- Crosslinking-polymerizing a monomer composition comprising a water-soluble ethylene-based unsaturated monomer having at least a portion of neutralized acidic groups in the presence of an internal crosslinking agent and a blowing agent to form a hydrogel polymer comprising a system 1 crosslinking polymer;
- the grinding of the hydrogel polymer is performed by pushing the hydrogel polymer into a porous plate having a plurality of holes by using a screw-type extruder mounted inside the cylindrical grinder, and having 20 to 35 (/ s) according to the following Formula 1 ) of the chopping rates: the manufacturing method of super-absorbent resin, is performed under the condition it is provided:
- ⁇ is the angular velocity of the screw in the screw extruder (2 ⁇ N / 60s), where ⁇ is the number of revolutions of the screw (rpm),
- first component may also be referred to as the second component, and similarly, the second component may be referred to as the first component.
- the term 'super absorbent polymer' means a base resin powder including a first crosslinked polymer of a water-soluble ethylenically unsaturated monomer having at least a part of a neutralized acid group; And a surface crosslinking layer formed on the base resin powder and including a second crosslinked polymer in which the first crosslinked polymer is further crosslinked through a surface crosslinking agent.
- the term 'foamed particles' refers to particles in which a concave portion formed by foaming occupies at least one third of the surface of a particle, as shown in FIG. 1A, and 'porous particles' refers to a surface as shown in FIG. 1B. It means a particle including three or more concave portions or pores having a depth of 10 or more.
- non-shear particles is a particle excluding the foamed particles and porous particles, as shown in Figure 1 (c) refers to the particles having a smooth surface as the shape deformation of the particles does not occur during the grinding process.
- the present inventors endeavored to produce a super absorbent polymer of excellent physical properties, as a result of introducing a foaming in the polymerization process as described below, when applying the appropriate shear force and compressive force in the grinding process, high absorption ratio, absorption rate which was difficult to achieve conventionally And it was confirmed that the super absorbent polymer which has fluid permeability can be manufactured.
- the superabsorbent polymer prepared by applying the foaming in the polymerization process and applying the appropriate shearing and compressing force in the pulverizing process, including the foamed particles and the porous particles at a high ratio has excellent CRC. , Pressure-absorbing capacity (AUP), physiological saline flow inducibility (SFC), and T-20 properties.
- AUP Pressure-absorbing capacity
- SFC physiological saline flow inducibility
- T-20 properties According to one embodiment of this invention,
- Pulverizing the hydrogel polymer is in the interior of the cylindrical grinder: throwing by using the mounting screw type extruder to push the hydrogel polymer to the perforated plate with a plurality of holes formed, according to the following equation 1 from 20 to 35 ( A process for preparing a super absorbent polymer, which is carried out under conditions of chopping index of / s), is provided:
- ⁇ is the angular velocity of the screw in the screw extruder (2 ⁇ X N / 60S), where ⁇ is the rotational speed of the screw (rpm),
- TSC is the solids content (%) of the hydrogel polymer introduced into the mill
- Step 1 is a step of preparing a hydrogel polymer, specifically, a monomer composition comprising a water-soluble ethylenically unsaturated monomer having at least a part of the neutralized acid group cross-polymerized in the presence of an internal crosslinking agent and a blowing agent to give a crosslinked polymer Forming a hydrogel containing a polymer.
- the water-soluble ethylenically unsaturated monomer may be any monomer conventionally used for preparing a super absorbent polymer.
- the water-soluble ethylenically unsaturated monomer may be a compound represented by the following formula (1):
- R 1 is an alkyl group having 2 to 5 carbon atoms containing an unsaturated bond
- M 1 is a hydrogen atom, a monovalent or divalent metal, an ammonium group or an organic amine salt.
- the water-soluble ethylenically unsaturated monomer may be at least one selected from the group consisting of acrylic acid,: methacrylic acid, and monovalent metal salts of these acids, ammonium salts and organic amine salts.
- acrylic acid or its salt is used as the water-soluble ethylenically unsaturated monomer, it is advantageous to obtain a superabsorbent polymer having improved water absorption.
- the monomers include maleic anhydride, fumaric acid, crotonic acid, itaconic acid, 2-acryloylethane sulfonic acid, 2-methacryloylethanesulfonic acid, 2- (meth) acryloylpropanesulfonic acid, or 2- ( Anionic monomers of meth) acrylamide-2-methyl propane sulfonic acid and salts thereof; (Meth) acrylamide, N-substituted (meth) acrylate, 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, mesopolyethylene glycol (meth) acrylate or polyethylene glycol ( Nonionic hydrophilic-containing monomers of meth) acrylate; And an amino group-containing unsaturated monomer of ( ⁇ , ⁇ ) -dimethylaminoethyl (meth) acrylate or ( ⁇ , ⁇ ) -dimethylaminopropyl (meth)
- the water-soluble ethylenically unsaturated monomer has an acidic group, at least a portion of the acidic group may be neutralized.
- those which have been partially neutralized with an alkali substance such as sodium hydroxide, potassium hydroxide, ammonium hydroxide and the like can be used.
- the degree of neutralization of the monomer may be 40 to 95 mol%, or 40 to 80 mol%, or 45 to 75 mol 0 /.
- the range of the degree of neutralization may vary depending on the final physical properties, but if the degree of neutralization is too high, it may be difficult for the polymerization to proceed smoothly due to precipitation of the thickened monomer.
- the monomer composition may include a polymerization initiator generally used in the preparation of a super absorbent polymer.
- a thermal polymerization initiator or a photopolymerization initiator may be used depending on the polymerization method.
- a thermal polymerization initiator since a certain amount of heat is generated by ultraviolet irradiation or the like, and a certain amount of heat is generated in accordance with the progress of the evaporation reaction, which is an exothermic reaction, a thermal polymerization initiator may be further included.
- photoinitiator for example, benzoin ether, dialkyl acetophenone, hydroxyl alkyl ketone, phenylglyoxylate, benzyldimethyl
- acylphosphine commercially available lucirin TPO, that is, 2,4,6-trimethyl-benzoyl-trimethyl phosphine oxide (2,4,6-trimethyl-benzoyl-trimethyl phosphine oxide) may be used. .
- thermopolymerization initiators are disclosed on page 115 of the Reinhold Schwalm book, "UV Coatings: Basics, Recent Developments and New Application (Elsevier, 2007)".
- a persulfate initiator an azo initiator, hydrogen peroxide, and ascorbic acid
- persulfate-based initiators include sodium persulfate (Na 2 S 2 O 8 ), potassium persulfate (Potassium persulfate; K 2 S 2 O 8 ), ammonium persulfate (NH 4 ) 2 S 2 0 8 ), and the like.
- azo-based initiators include 2,2-azobis- (2-amidinopropane) dihydrochloride (2,2-azobis (2-amidinopropane) dihydrochloride), 2,2-azobis- ( ⁇ , ⁇ -dimethylene) isobutyramidine dihydrochloride (2,2-azobis- (N, N-dimethylene) isobutyramidine dihydrochloride), 2-
- Such a polymerization initiator may be added at a concentration of about 0.001 to 1% by weight based on the monomer composition.
- concentration of the polymerization initiator is too low, the polymerization rate may be slow and a large amount of the remaining monomers may be extracted in the final product.
- concentration of the polymerization initiator is too high, it is not preferable because the polymer chain constituting the network is shortened, so that the content of the water-soluble component is high and the pressure absorption capacity is lowered.
- the polymerization of the monomer composition is carried out in the presence of a crosslinking agent ("internal crosslinking agent") in order to improve the physical properties of the resin by the polymerization of the water-soluble ethylenically unsaturated monomer.
- the crosslinking agent is for internal crosslinking of the hydrogel polymer, and may be used separately from the "surface crosslinking agent" to be described later.
- the internal crosslinking agent any compound may be used as long as it enables the introduction of a crosslink during polymerization of the water-soluble ethylene-based unsaturated monomer.
- the internal crosslinking agent is ⁇ , ⁇ '- methylenebisacrylamide, trimethyl propane tri (meth) acrylate, ethylene glycol di (meth) acrylate, polyethylene glycol di (meth) acrylate, Propylene glycol di (meth) acrylate, Polypropylene glycol di (meth) acrylate, Butanediol di (meth) acrylate, Butylene glycol di (meth) acrylate, Diethylene glycol di (meth) acrylate, Nucleic acid Dioldi (meth) acrylate Triethyleneglycol Di (meth) acrylate, Tripropyleneglycol Di (meth) acrylate, Tetraethyleneglycol Di (meth) acrylate, Dipentaerythrite Pentaacrylate, Glycerine Tri (meth ) Acrylate, pentaeryes alone or in combination of two or more polyfunctional crosslinking agents such as tetraacrylate, triallyl
- Such internal crosslinking agent is present in about 0.001 to 1 weight percent of the monomer composition. May be added at a concentration. That is, when the concentration of the internal crosslinking agent is too low, the absorption rate of the resin may be lowered and the gel strength may be weakened, which is not preferable. On the contrary, when the concentration of the internal crosslinking agent is too high, the absorptivity of the resin may be lowered, which may be undesirable as an absorber.
- crosslinking polymerization of the monomer composition is carried out in the presence of a blowing agent. The blowing agent may form pores by decomposition during the polymerization and crosslinking reaction of step 1.
- the blowing agent is sodium bicarbonate, sodium carbonate, potassium bicarbonate, potassium carbonate, calcium bicarbonate, calcium carbonate, calcium carbonate bicarbonate), magnesium bicarbonate, magnesium ⁇ ! "magnesium carbonate, ⁇
- the blowing agent is preferably present in the monomer composition in the amount of 1000 to 3000 ppm in order to achieve the foaming of the degree required in the present invention when performing step 1.
- the blowing agent is at least 1000 ppm, or at least 1100 ppm, or at least 1200 ppm in the monomer composition; And up to 3000 ppm, or up to 2500 ppm, and black up to 2000 ppm.
- the monomer composition may further include additives such as thickeners, plasticizers, storage stabilizers, and antioxidants as necessary. And such a monomer composition is the above-mentioned water-soluble ethyl
- Raw materials such as monomers, polymerization initiators, internal crosslinking agents and blowing agents are used.
- the solvent includes water, ethanol, ethylene glycol, diethylene glycol, triethylene glycol, 1,4-butanedi, propylene glycol, ethylene glycol monobutyl ether, propylene glycol monomethyl ether, propylene glycol monomethyl ether.
- Formation of the hydrogel polymer through the polymerization of the monomer composition may be carried out by a conventional polymerization method, the process is not particularly limited.
- the polymerization method is largely divided into thermal polymerization and photopolymerization according to the type of polymerization energy source.
- the process may be performed in a semi-unggi machine having a stirring shaft, such as a kneader, or, in the case of performing the light integration, may be performed in a reactor equipped with a movable conveyor belt.
- the hydrogel polymer may be obtained by adding the monomer composition to a reactor such as a kneader equipped with a stirring shaft and supplying hot air thereto or by heating and heating the reactor.
- the hydrogel polymer discharged to the reactor outlet depending on the shape of the stirring shaft provided in the reactor may be obtained in the particles of several millimeters to several centimeters.
- the resulting hydrogel polymer may be obtained in various forms according to the concentration and injection speed of the monomer composition to be injected, and a hydrogel polymer having a particle size of 2 to 50 mm (weight average) in general may be obtained.
- a hydrous gel polymer in a sheet form may be obtained.
- the thickness of the sheet may vary depending on the concentration and the injection speed of the monomer composition to be injected, in order to ensure the production rate, while the entire sheet is evenly polymerized, it is usually adjusted to a thickness of 0.5 to 10 cm desirable.
- the hydrogel polymer formed in this manner can exhibit a water content of about 40 to 80% by weight.
- the moisture content is a weight of water in the total weight of the hydrogel polymer, it may be a value obtained by subtracting the weight of the dry polymer from the weight of the hydrogel polymer. Specifically, it may be defined as a value calculated by measuring the weight loss due to evaporation of water in the polymer in the process of raising the temperature of the polymer through infrared heating.
- the drying conditions may be set to 20 minutes, including 5 minutes of the temperature rise step in such a way that the temperature is increased to about 180 ° C at room temperature and maintained at 18 CTC.
- step 2 the hydrogel polymer prepared in step 1
- the hydrogel polymer may be ground to reduce its size (ie, to increase the surface area) to increase the efficiency of subsequent drying.
- the shape of the hydrogel polymer may be controlled by adjusting the grinding conditions, thereby improving physical properties of the super absorbent polymer.
- the pulverizer used is not limited in configuration, but specifically, a vertical pulverizer, a turbo cutter, a turbo grinder, a rotary cutter mill, a cutting machine Any one selected from the group of grinding machines consisting of a cutter mill, a disc mill, a shred crusher, a crusher, a chopper, and a disc cutter It may include, but is not limited to the above-described example.
- the shear gel and the compressive force acts on the hydrogel polymer in the present invention is characterized by controlling such grinding conditions. The shear force is associated with the force acting when the hydrogel polymer is pushed into the grinder, and the compressive force is associated with the force acting as the hydrogel polymer passes through the grinder.
- the step of pulverizing the hydrogel polymer by pushing the hydrogel polymer to the porous plate formed with a plurality of holes using a screw-type extruder mounted inside the cylindrical grinder, 20 to 20 according to the formula It is performed under the condition of a chopping index of 35 (/ s).
- ⁇ is the angular velocity of the screw in the screw extruder (2 ⁇ X N / 60s), where ⁇ is the rotational speed of the screw (rpm),
- TSC is the solids content (%) of the hydrogel polymer introduced into the mill
- A is the aperture ratio of the porous plate ( ⁇ 2 X n IR 2 ), where r is the The radius of the holes formed in the porous plate (mm), n is the number of holes formed in the porous plate, and R is the radius of the porous plate (mm).
- the grinding of step 2 is at least 20 (/ s), or at least 21 (/ s), or at least 22 (/ s), or at least 23 (/ s), or at least 24 (/ s); And less than 35 (/ s), or less than 32.5 (/ s), or less than 31 (/ s), and less than 30.5 (/ s), or less than 30.1 (/ s).
- the grinding is preferably performed under the condition of chopping index of 20 (/ s) or more.
- the choke index applied in step 2 is high, the absorption rate under pressure may be improved, but there may be a problem that the balance between absorption and permeability deteriorates. Therefore, the grinding
- the grinding produces hydrogel polymer particles of various shapes.
- the particles formed by the pulverization may include 'foamed particles', wherein the concave portions by foaming occupy 1/3 or more of the particle surface as shown in FIG. 'Porous particles' which are particles including three or more concave portions or pores having a depth of 10 m or more on the surface as shown in FIG. 1 (b); As the particles excluding the expanded particles and the porous particles, as shown in (c) of FIG.
- the proportion of the expanded particles in the milled hydrogel polymer according to step 2 is 10% or more, or 10 To 20%, or 10 to 15%.
- the ratio of the sum of the expanded particles and the porous particles is 50% or more of the total particle number, Alternatively 50 to 70%, Or 55-70%.
- the superabsorbent polymer of the Example prepared under the conditions of the chopping index together with the foaming, while satisfying the ratio and physical properties for each particle type required in the present invention, the superabsorbent of the comparative example not The resin does not satisfy the ratio and physical properties of the particle types required in the present invention.
- the proportion of the foamed particles may appear to be 10% or more of the total number of particles
- the foamed particles cannot be satisfied when the conditions of the chopping index are not satisfied in the grinding.
- the proportion of the sum of the porous particles falls below 50% of the total particle number.
- Grinding of the hydrogel polymer may be performed so that the particle diameter of the hydrogel polymer is 0.1 mm to 10 mm.
- the hydrogel polymer is preferably pulverized into particles of 10 mm or less.
- the hydrogel polymer is preferably pulverized into particles of 0.1 mm or more.
- the pulverization of the hydrogel polymer may be a phenomenon in which the hydrogel polymer adheres to the surface of the pulverizer because the hydrogel polymer is performed at a high water content.
- Step 3 is a step of drying the hydrogel polymer pulverized in the step 2.
- the drying is 120 to 250 ° C, preferably 140 to 200 ° C, more Preferably it may be carried out under a temperature of 150 to 19C C.
- the drying temperature may be defined as the temperature of the heat medium supplied for drying or the temperature inside the drying reactor including the heat medium and the polymer in the drying process. If the drying temperature is low and the drying time is long, the process efficiency is lowered. In order to prevent this, the drying temperature is preferably 120 ° C. or more.
- the drying temperature is higher than necessary, the surface of the hydrogel polymer may be excessively dried to increase the generation of fine powder in the subsequent grinding step, and the physical properties of the final resin may be lowered. It is preferred that it is 250 ° C or less.
- the drying time in the drying step is not particularly limited, but may be adjusted to 20 to 90 minutes under the drying temperature in consideration of process efficiency and the physical properties of the resin.
- the drying may be performed using a conventional medium.
- the drying may be performed by supplying hot air to the pulverized hydrogel polymer, infrared irradiation, microwave irradiation, or ultraviolet irradiation.
- such drying is preferably carried out by a dry polymer increases so as to have a water content of about 0.1 to 10 parts by weight 0 /. That is, the moisture content of the dried polymer
- Step 4 is a step of pulverizing the polymer dried in step 3, to optimize the surface area.
- the milling may be performed such that the particle diameter of the milled polymer is 150 to 850 m.
- the grinder that can be used at this time is a pin mill, hammer mill, Screw mills, rail mills, disc mills, jog mills and the like can be used.
- the step of selectively classifying particles having a particle size of 1 50 to 850 from the polymer particles obtained through the grinding step may be further performed.
- the fine particles having a particle size of less than 150 im can be assembled with a solvent (for example, water) that can be used in step 1 to prepare a fine powder reassembly.
- the fine powder reassembly may be added to the hydrogel polymer of step 2 described above. Specifically, the addition of the fine powder reassembly may be performed immediately before, during or after the grinding of step 2.
- Step 5 is surface modification of the polymer pulverized in step 4.
- the surface modification induces a crosslinking reaction on the surface of the pulverized polymer in the presence of a second crosslinking agent (surface crosslinking agent), and through the surface modification, a surface modification layer (surface crosslinking layer) is formed on the surface of the pulverized polymer particles. Is formed.
- the surface modification can be carried out by a conventional method of increasing the crosslinking density of the surface of the polymer particles, for example, a method of mixing and crosslinking the pulverized polymer with a solution containing a second crosslinking agent (surface crosslinking agent). It can be performed as.
- the second crosslinking agent is preferably a compound capable of reacting with the functional group of the polymer, and preferably an alkylene carbonate having 2 to 5 carbon atoms. More preferably, ethylene carbonate can be used as the second crosslinking agent.
- porous silica or clay may be further included.
- an acidic compound, a polymer, or the like may be further added in order to adjust the penetration rate and depth of the second crosslinking agent.
- the content of the second crosslinking agent may be appropriately adjusted according to the type or reaction conditions of the crosslinking agent, and preferably, the amount may be adjusted to 0.001 to 5 parts by weight based on 100 parts by weight of the pulverized polymer.
- the content of the second crosslinking agent is too low, surface modification may not be performed properly and the physical properties of the final resin may be lowered.
- an excessive amount of the second crosslinking agent is used, the absorbency of the resin may be rather negligible due to excessive surface crosslinking reaction, which is not preferable.
- the surface modification step the method of mixing the Crab 2 cross-linking agent and the pulverized polymer in a semi-permanent mixture, the method of spraying a second cross-linking agent to the pulverized polymer, the pulverized polymer and the second cross-linking agent in a mixer that is continuously operated It can be carried out by conventional methods, such as the method of supplying continuously and mixing.
- water may be additionally added when the second crosslinking agent is added. As such, when the second crosslinking agent and water are added together, even dispersion of the second crosslinking agent can be induced, aggregation of polymer particles can be prevented, and penetration depth of the second crosslinking agent into the polymer particles can be further optimized.
- the content of water added with the second crosslinking agent may be adjusted to 0.5 to 10 parts by weight based on 100 parts by weight of the pulverized polymer.
- the surface modification step may be performed under a temperature of 100 to 250 ° C.
- the surface modification may be performed for 1 minute to 120 minutes, preferably 1 minute to 100 minutes, more preferably 10 minutes to 80 minutes. That is, the surface modification step may be performed under the above-described conditions in order to induce a minimum surface crosslinking reaction and to prevent deterioration of physical properties due to damage of the polymer particles during excessive reaction.
- a super absorbent polymer prepared according to the above-described method.
- the super absorbent polymer may include a base resin powder including a system 1 cross-linked polymer of a water-soluble ethylenically unsaturated monomer having at least a part of neutralized acid groups; And a surface crosslinking layer formed on the base resin powder, the first crosslinking polymer comprising a second crosslinking polymer further crosslinked via a surface crosslinking agent.
- the super absorbent polymer is obtained as particles having a particle diameter of 150 to 850.
- the superabsorbent polymer as prepared by the method described above, has an excellent absorption ratio, absorption rate, and liquid permeability, which are centrifugal water retention capacity (CRC), pressure absorption capacity (AUP), and physiological saline flow induction ( SFC), T-20 and the like can be expressed in physical properties.
- the superabsorbent polymer has a centrifugal water retention capacity (CRC) of 30 g / g for physiological saline (0.9 weight 0 / ° sodium chloride aqueous solution) for 26 minutes, preferably 26.5 g / g or more, or 27 g / g or more, or 27.4 g / g or more.
- the CRC is not limited to the upper limit because the value is excellent, for example, the CRC of the super absorbent polymer is 30 g / g or less, or 29.5 g / g or less, or 29 g / g or less, or 28.5 g / or less than g.
- the CRC of the superabsorbent polymer may be measured according to the European Disposables and Nonwovens Association (EDANA) standard EDANA WSP 241 .3, and may be calculated according to Formula A described in Test Examples herein.
- the superabsorbent polymer has a pressurized absorption capacity (AUP) of at least 21 g / g for 1 hour under 0.7 psi in physiological saline solution (0.9 wt% aqueous sodium chloride solution), preferably 22 g / g or more, or 23 g / g. Or 23.4 g / g or more.
- the AUP of the superabsorbent polymer may be 29 g / g or less, or 28 g / g or less, or 27 g / g or less.
- the AUP of the superabsorbent polymer may be measured according to the method of the European Disposables and Nonwovens Association standard EDANA WSP 242.3, and may be calculated according to the formula B described in the test examples herein.
- the superabsorbent polymer has a flow inducibility (SFC, 1 Cr 7 cm 3 "s / g) of physiological saline (0.685 weight 0 /. Sodium chloride aqueous solution) of 35 or more, preferably 37 or more. The higher the better, there is no limit to the upper limit, for example, the SFC of the super absorbent polymer may be 100 or less, 90 or less, or 80 or less.
- the SFC can be measured and calculated according to methods well known to those skilled in the art, for example, as disclosed in columns 54 to 59 of US Pat. No. 5562646.
- the super-absorbent resin, and water-absorbing resin 1 g of 0.9 wt. 0 /. Sodium chloride and 0.01 wt. 0 /.
- T-20 190 represents the time required to absorb the alcohol eteuk salicylate aqueous solution of 20 g of a carbon number of 12 to 14 Seconds or less, preferably 180 seconds or less, or 170 seconds or less. The smaller the T-20 is, the better it is, so there is no limit to the lower limit.
- the T-20 of the superabsorbent polymer may be 80 seconds or more, 90 seconds or more, 100 seconds or more, or 110 seconds or more.
- T-20 of the superabsorbent polymer was prepared by dissolving 9 g of sodium chloride and 0.1 g of Lorodac (main component: linear ethoxylated alcohol having 12 to 14 carbon atoms, CAS # 68439-50-9) in 1 L of distilled water. Can be calculated and measured as the time (in seconds) for 1 g of superabsorbent resin to absorb 20 g of this aqueous solution.
- Lorodac main component: linear ethoxylated alcohol having 12 to 14 carbon atoms, CAS # 68439-50-9
- the manufacturing method of the superabsorbent polymer according to the present invention makes it possible to provide a superabsorbent polymer having excellent absorption ratio, absorption rate and liquid permeability.
- a super absorbent polymer can be suitably used as a hygiene material such as a diaper, in particular an ultra-thin hygiene material.
- FIG. 1 is foamed particles [FIG. 1 (a)], wherein the recessed portion due to foaming in the superabsorbent polymer particles prepared according to Example 1 of the present invention occupies at least 1/3 of the surface of the particle.
- Porous particles that are particles containing three or more concave portions or pores of fm or more [FIG. 1 (b)] and non-shear particles that are particles having a smooth surface due to no morphological deformation of the particles during the grinding process [FIG. )] Is a SEM image.
- the superabsorbent polymer manufacturing apparatus includes a continuous manufacturing apparatus comprising a polymerization process, a hydrogel grinding process, a drying process, a grinding process, a classification process, a surface crosslinking process, a engraving process, a classification process, and a transportation process connecting each process. Used.
- the hydrogel polymer pulverized in step 2 was dried in a drier capable of transferring air volume up and down.
- the hot water at 180 ° C. was flowed downwardly upwards for 15 minutes, and then flows upwards and downwards for 15 minutes, so that the water-containing gel dried product was uniform. Dried. '
- the dried polymer in step 3 was pulverized with a grinder and then classified to obtain a base resin having a size of 150 to 850 urn.
- Superabsorbent resin particles were observed with a scanning electron microscope (SEM), and foamed particles, in which the concave portion occupied at least one third of the particle surface by total particle evaporation (classified as porous particles when the ratio was less than 1/3)
- SEM scanning electron microscope
- the ratio of the non-shear particles which are particles having a smooth surface because no morphological deformation of the particles, and particles having three or more recesses or pores having a depth of 10 / m or more and three or more pores, were calculated.
- the centrifugal water retention capacity was measured by the no-load absorption factor in accordance with the European Disposables and Nonwovens Association (EDANA) standard EDANA WSP 241.3.
- the superabsorbent resin W 0 (g, about 0.2g) after the insert uniformly in the envelope of the nonwoven fabric is sealed (seal), it was submerged in the saline solution of sodium chloride solution of 0.9 weight 0 /. To room temperature. After 30 minutes, the envelope was centrifuged and drained at 250 G for 3 minutes, and then the mass W 2 (g) of the envelope was measured. In addition, the mass ⁇ Z g) at that time was measured after performing the same operation without using a super absorbent polymer. Using each mass thus obtained, CRC (g / g) was calculated according to the following formula A to confirm the water holding capacity.
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US16/086,244 US11712678B2 (en) | 2017-01-24 | 2017-12-26 | Preparation method of super absorbent polymer |
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WO2022196763A1 (ja) | 2021-03-18 | 2022-09-22 | 株式会社日本触媒 | 吸水性樹脂の製造方法 |
WO2022197991A1 (en) | 2021-03-18 | 2022-09-22 | The Procter & Gamble Company | Method for producing absorbent articles comprising water-absorbing resin |
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CN108779265A (zh) | 2018-11-09 |
EP3406655A4 (en) | 2019-06-19 |
KR102086058B1 (ko) | 2020-03-06 |
EP3406655A1 (en) | 2018-11-28 |
CN108779265B (zh) | 2021-01-08 |
US11712678B2 (en) | 2023-08-01 |
JP6728396B2 (ja) | 2020-07-22 |
KR20180087049A (ko) | 2018-08-01 |
JP2019518821A (ja) | 2019-07-04 |
US20200164344A1 (en) | 2020-05-28 |
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