JP6227140B2 - 逆相重合法 - Google Patents
逆相重合法 Download PDFInfo
- Publication number
- JP6227140B2 JP6227140B2 JP2016530487A JP2016530487A JP6227140B2 JP 6227140 B2 JP6227140 B2 JP 6227140B2 JP 2016530487 A JP2016530487 A JP 2016530487A JP 2016530487 A JP2016530487 A JP 2016530487A JP 6227140 B2 JP6227140 B2 JP 6227140B2
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- JP
- Japan
- Prior art keywords
- aqueous liquid
- monomer
- beads
- aqueous
- polymer
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
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- 238000006116 polymerization reaction Methods 0.000 title claims description 97
- 239000000178 monomer Substances 0.000 claims description 289
- 239000007788 liquid Substances 0.000 claims description 257
- 239000011324 bead Substances 0.000 claims description 235
- 229920000642 polymer Polymers 0.000 claims description 165
- 238000000034 method Methods 0.000 claims description 118
- 239000000203 mixture Substances 0.000 claims description 82
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 57
- 230000008569 process Effects 0.000 claims description 40
- 239000012528 membrane Substances 0.000 claims description 36
- 238000001914 filtration Methods 0.000 claims description 35
- 230000002441 reversible effect Effects 0.000 claims description 33
- 238000004140 cleaning Methods 0.000 claims description 30
- 239000000725 suspension Substances 0.000 claims description 30
- 150000003839 salts Chemical class 0.000 claims description 28
- 238000010557 suspension polymerization reaction Methods 0.000 claims description 28
- 239000012535 impurity Substances 0.000 claims description 25
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 24
- 238000009295 crossflow filtration Methods 0.000 claims description 21
- 239000002245 particle Substances 0.000 claims description 21
- 239000007864 aqueous solution Substances 0.000 claims description 16
- 239000003381 stabilizer Substances 0.000 claims description 15
- 238000001704 evaporation Methods 0.000 claims description 13
- 230000008020 evaporation Effects 0.000 claims description 11
- 238000001125 extrusion Methods 0.000 claims description 11
- 230000000379 polymerizing effect Effects 0.000 claims description 10
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 9
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 8
- 239000000843 powder Substances 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 7
- 239000011148 porous material Substances 0.000 claims description 7
- 238000010170 biological method Methods 0.000 claims description 5
- 230000000977 initiatory effect Effects 0.000 claims description 5
- 239000000126 substance Substances 0.000 claims description 5
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 4
- 230000003197 catalytic effect Effects 0.000 claims description 4
- 238000000227 grinding Methods 0.000 claims description 4
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 claims description 4
- DPBJAVGHACCNRL-UHFFFAOYSA-N 2-(dimethylamino)ethyl prop-2-enoate Chemical compound CN(C)CCOC(=O)C=C DPBJAVGHACCNRL-UHFFFAOYSA-N 0.000 claims description 3
- 238000009833 condensation Methods 0.000 claims description 3
- 230000005494 condensation Effects 0.000 claims description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 3
- 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
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 2
- 239000011976 maleic acid Substances 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
- NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical compound OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 claims description 2
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims 4
- JKNCOURZONDCGV-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-methylprop-2-enoate Chemical compound CN(C)CCOC(=O)C(C)=C JKNCOURZONDCGV-UHFFFAOYSA-N 0.000 claims 1
- AIIITCMZOKMJIM-UHFFFAOYSA-N 2-(prop-2-enoylamino)propane-2-sulfonic acid Chemical compound OS(=O)(=O)C(C)(C)NC(=O)C=C AIIITCMZOKMJIM-UHFFFAOYSA-N 0.000 claims 1
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 claims 1
- ZWAPMFBHEQZLGK-UHFFFAOYSA-N 5-(dimethylamino)-2-methylidenepentanamide Chemical compound CN(C)CCCC(=C)C(N)=O ZWAPMFBHEQZLGK-UHFFFAOYSA-N 0.000 claims 1
- UIIIBRHUICCMAI-UHFFFAOYSA-N prop-2-ene-1-sulfonic acid Chemical compound OS(=O)(=O)CC=C UIIIBRHUICCMAI-UHFFFAOYSA-N 0.000 claims 1
- -1 azo compound Chemical class 0.000 description 36
- 229910052757 nitrogen Inorganic materials 0.000 description 34
- 239000001257 hydrogen Substances 0.000 description 28
- 229910052739 hydrogen Inorganic materials 0.000 description 28
- 239000003999 initiator Substances 0.000 description 23
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 20
- 239000000463 material Substances 0.000 description 17
- 125000000217 alkyl group Chemical group 0.000 description 16
- 150000002431 hydrogen Chemical class 0.000 description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 13
- 238000005406 washing Methods 0.000 description 13
- 229910052783 alkali metal Inorganic materials 0.000 description 12
- 239000000047 product Substances 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 10
- 239000012141 concentrate Substances 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 8
- 239000003431 cross linking reagent Substances 0.000 description 8
- 239000010408 film Substances 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 8
- 125000003710 aryl alkyl group Chemical group 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 150000002148 esters Chemical class 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 6
- 125000003342 alkenyl group Chemical group 0.000 description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 6
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 6
- 239000011521 glass Substances 0.000 description 6
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 6
- 238000001471 micro-filtration Methods 0.000 description 6
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 230000003068 static effect Effects 0.000 description 6
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
- 238000000108 ultra-filtration Methods 0.000 description 6
- 229920003169 water-soluble polymer Polymers 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 5
- 150000001340 alkali metals Chemical class 0.000 description 5
- 150000001408 amides Chemical class 0.000 description 5
- 125000002091 cationic group Chemical group 0.000 description 5
- 239000003518 caustics Substances 0.000 description 5
- 239000003638 chemical reducing agent Substances 0.000 description 5
- 238000004581 coalescence Methods 0.000 description 5
- 238000007872 degassing Methods 0.000 description 5
- 238000009826 distribution Methods 0.000 description 5
- 230000007935 neutral effect Effects 0.000 description 5
- 239000007800 oxidant agent Substances 0.000 description 5
- 150000002978 peroxides Chemical class 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- 238000012719 thermal polymerization Methods 0.000 description 5
- 238000012546 transfer Methods 0.000 description 5
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 4
- 239000005977 Ethylene Substances 0.000 description 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 4
- 125000000129 anionic group Chemical group 0.000 description 4
- 150000001450 anions Chemical class 0.000 description 4
- 230000001174 ascending effect Effects 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
- 150000001768 cations Chemical class 0.000 description 4
- 238000005119 centrifugation Methods 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 239000000084 colloidal system Substances 0.000 description 4
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 239000012530 fluid Substances 0.000 description 4
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 239000012466 permeate Substances 0.000 description 4
- JRKICGRDRMAZLK-UHFFFAOYSA-L peroxydisulfate Chemical compound [O-]S(=O)(=O)OOS([O-])(=O)=O JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 4
- 238000011045 prefiltration Methods 0.000 description 4
- 230000001681 protective effect Effects 0.000 description 4
- 230000005855 radiation Effects 0.000 description 4
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 4
- 239000002562 thickening agent Substances 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000013019 agitation Methods 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 239000000919 ceramic Substances 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- IMBKASBLAKCLEM-UHFFFAOYSA-L ferrous ammonium sulfate (anhydrous) Chemical compound [NH4+].[NH4+].[Fe+2].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O IMBKASBLAKCLEM-UHFFFAOYSA-L 0.000 description 3
- 239000010419 fine particle Substances 0.000 description 3
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 229940050176 methyl chloride Drugs 0.000 description 3
- 239000004530 micro-emulsion Substances 0.000 description 3
- ZQXSMRAEXCEDJD-UHFFFAOYSA-N n-ethenylformamide Chemical compound C=CNC=O ZQXSMRAEXCEDJD-UHFFFAOYSA-N 0.000 description 3
- 238000001728 nano-filtration Methods 0.000 description 3
- 229920002401 polyacrylamide Polymers 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 230000010349 pulsation Effects 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000010409 thin film Substances 0.000 description 3
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2,2'-azo-bis-isobutyronitrile Substances N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 2
- 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 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 2
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 2
- 229910000851 Alloy steel Inorganic materials 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
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
- 239000004971 Cross linker Substances 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 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
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 239000002033 PVDF binder Substances 0.000 description 2
- 239000004695 Polyether sulfone Substances 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 2
- 238000009825 accumulation Methods 0.000 description 2
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- 239000012670 alkaline solution Substances 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
- 238000013459 approach Methods 0.000 description 2
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 229940073608 benzyl chloride Drugs 0.000 description 2
- CADWTSSKOVRVJC-UHFFFAOYSA-N benzyl(dimethyl)azanium;chloride Chemical compound [Cl-].C[NH+](C)CC1=CC=CC=C1 CADWTSSKOVRVJC-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- SXDBWCPKPHAZSM-UHFFFAOYSA-M bromate Chemical class [O-]Br(=O)=O SXDBWCPKPHAZSM-UHFFFAOYSA-M 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 229910010293 ceramic material Inorganic materials 0.000 description 2
- 239000000701 coagulant Substances 0.000 description 2
- 238000004891 communication Methods 0.000 description 2
- 238000010924 continuous production Methods 0.000 description 2
- 238000005260 corrosion Methods 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- PFKRTWCFCOUBHS-UHFFFAOYSA-N dimethyl(octadecyl)azanium;chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCC[NH+](C)C PFKRTWCFCOUBHS-UHFFFAOYSA-N 0.000 description 2
- DLFDEDJIVYYWTB-UHFFFAOYSA-N dodecyl(dimethyl)azanium;bromide Chemical compound Br.CCCCCCCCCCCCN(C)C DLFDEDJIVYYWTB-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 230000005484 gravity Effects 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 230000014759 maintenance of location Effects 0.000 description 2
- 238000003801 milling Methods 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- NULGSOGHGHDGBH-UHFFFAOYSA-N n,n-dimethyl-1-phenylmethanamine;hydrobromide Chemical compound [Br-].C[NH+](C)CC1=CC=CC=C1 NULGSOGHGHDGBH-UHFFFAOYSA-N 0.000 description 2
- QYZFTMMPKCOTAN-UHFFFAOYSA-N n-[2-(2-hydroxyethylamino)ethyl]-2-[[1-[2-(2-hydroxyethylamino)ethylamino]-2-methyl-1-oxopropan-2-yl]diazenyl]-2-methylpropanamide Chemical compound OCCNCCNC(=O)C(C)(C)N=NC(C)(C)C(=O)NCCNCCO QYZFTMMPKCOTAN-UHFFFAOYSA-N 0.000 description 2
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
- HMZGPNHSPWNGEP-UHFFFAOYSA-N octadecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)C(C)=C HMZGPNHSPWNGEP-UHFFFAOYSA-N 0.000 description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
- 229920000371 poly(diallyldimethylammonium chloride) polymer Polymers 0.000 description 2
- 229920002492 poly(sulfone) Polymers 0.000 description 2
- 229920006393 polyether sulfone Polymers 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 2
- 239000004810 polytetrafluoroethylene Substances 0.000 description 2
- 229920002981 polyvinylidene fluoride Polymers 0.000 description 2
- XXQBEVHPUKOQEO-UHFFFAOYSA-N potassium superoxide Chemical compound [K+].[K+].[O-][O-] XXQBEVHPUKOQEO-UHFFFAOYSA-N 0.000 description 2
- 238000005086 pumping Methods 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 239000012966 redox initiator Substances 0.000 description 2
- 230000002829 reductive effect Effects 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical group [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical class [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 2
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 2
- 150000003568 thioethers Chemical class 0.000 description 2
- 150000004764 thiosulfuric acid derivatives Chemical class 0.000 description 2
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Images
Classifications
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Description
容器(1)中に前記非水性液体を準備すること、
前記非水性液体中の前記水性モノマーまたはモノマーブレンドからのモノマービーズの懸濁液を形成すること、
重合を開始することにより重合中ビーズを形成すること、
非水性液体中の前記ポリマービーズの懸濁液を前記容器から取り出すこと、および、水溶性または水膨潤性ポリマービーズを前記懸濁液から回収すること、その際、前記非水性液体は粒子を含有する不純物を含むものとする、
および、次いで前記懸濁液からの前記非水性液体を清浄化段階へと移すこと
を含み、その際、前記清浄化段階によって逆相懸濁重合法における使用に適した清浄化された非水性液体を提供し、ここで、前記清浄化段階は、少なくとも1つのろ過ステップにおいて前記非水性液体から粒子を除去することを含むものとする。
非水性液体の収容に適した容器(1)、
前記非水性液体中の水性モノマービーズの懸濁液を形成するための手段、
前記非水性液体中の前記ポリマービーズの懸濁液を前記容器から取り出すための手段、
水溶性または水膨潤性ポリマービーズを前記懸濁液から回収するための手段、
少なくとも1つのろ過ステップにより前記非水性液体を清浄化するための手段であって、それにより、前記清浄化された非水性液体が逆相重合法における使用に適したものとなる、前記手段。
i)100nm未満、好ましくは50nm未満、さらに好ましくは1〜45nm、最も好ましくは1nm〜40nmの範囲内、例えば10nm〜40nmの範囲内の平均孔径;
または
ii)150,000Da未満、好ましくは60,000Da未満、例えば5,000Da〜60,000Daの分画分子量(MWCO)。
R1、R2およびR3は、同一であるかまたは異なり、かつ、水素、C1〜2−アルキル、カルボキシ、またはカルボキシで置換されたC1〜2−アルキルである]
のカルボン酸またはその塩、
式
のアミド、ビニル誘導体またはジアリルアンモニウム誘導体であることができる。
式
R1、R2およびR3は、同一であるかまたは異なり、かつ、水素、またはメチル、またはカルボキシ、またはカルボキシで置換されたメチルである]
のカルボン酸またはその塩、式
のエステル、式
のアミド。
式
R1は、水素またはメチルであり、かつR2およびR3は共に水素である]
のカルボン酸またはその塩、式
のエステル、式
のアミド。
アクリル酸またはその塩、式
のエステル、アクリルアミド、および式
のアミド。
アクリル酸またはその塩、および式
のエステル。
アクリル酸またはその塩、および式
のエステル。
R1、R2、R3、R4、R5、R6は、独立して、水素、または1〜4個の炭素を含むアルキル鎖であることができ、
Qは、1〜8個の炭素を含むアルキル鎖であることができ、
R7は、6〜30個の炭素を含むアルキルまたはアルケニルまたはアリールアルキル鎖であることができ、
Xは、塩化物イオン、臭化物イオン、ヨウ化物イオン、フッ化物イオンを含む群から選択されるハロゲン化物イオンであるか、または負の電荷を有する対イオンであることができる]。
kおよびlは、独立して、0〜100の範囲内に含まれる2つの正の実数であり、かつk+l>3であり、
R1は、水素であるか、または1〜4個の炭素を含むアルキル鎖であってよく、
R2は、1〜30個の炭素を含むアルキル、アルケニルまたはアリールアルキル鎖であってよく、
Qは、OまたはNR4であってよく、ここで、R4は、H、アルキル、シクロアルキル、ヘテロシクロアルキル、アリールまたはヘタリールから選択され、
R3は、Hであるか、または1〜30個の炭素を含むアルキル基であるか、または3〜30個の炭素を含むアルケニル基であるか、または6〜30個の炭素を含むアリールアルキル鎖であってよく、
好ましくは、R1は水素原子またはメチル基のいずれかであり、
好ましくは、kは、3〜50の範囲内に含まれる実数であり、これによって水への溶解性がもたらされ、
好ましくは、lは0〜30の範囲内に含まれる実数である。
kは、0〜100の範囲内に含まれる正の実数であり、
R1は、水素であるか、または1〜4個の炭素を含むアルキル鎖であることができ、
R2は、1〜30個の炭素を含むアルキル、アルケニルまたはアリールアルキル鎖であることができ、
Qは、OまたはNR4であってよく、ここで、R4は、水素であるか、または1〜4個の炭素を含むアルキル基であってよく、
R3は、Hであるか、または1〜30個の炭素を含むアルキル基であるか、または3〜30個の炭素を含むアルケニル基であるか、または6〜30個の炭素を含むアリールアルキル鎖であってよく、
好ましくは、R1は水素原子またはメチル基のいずれかであり、
好ましくは、kは、3〜50の範囲内に含まれる実数であり、これによって水への溶解性がもたらされ、
好ましくは、lは0〜30の範囲内に含まれる実数である]
により定義されうる。
kおよびlおよびmは、独立して、0〜100の範囲内に含まれる3つの正の実数であり、かつk+l+m>3であり、
R1は、水素であるか、または1〜4個の炭素を含むアルキル鎖であってよく、
R2は、−(CnH2n)−、または−O−(CnH2n)−、または−C(O)−O−CnH2n)−、または−C(O)−NR7−CnH2n)−のいずれかであってよく、ここで、R7は、水素であるか、または1〜4個の炭素を含むアルキルであってよい。R2の4つの異なる全ての構造において、nは1〜6の整数である。
R3、R4、R5は、独立して、Hであるか、または1〜30個の炭素を含むアルキル基であるか、または6〜30個の炭素を含むアリールアルキル基である。
R6は、Hであるか、または1〜30個の炭素を含むアルキル基であるか、または3〜30個の炭素を含むアルケニル基であるか、または6〜30個の炭素を含むアリールアルキル鎖であることができる。
好ましくは、R1は、水素原子またはメチル基のいずれかである。
式(VI)に関する好ましいR3、R4またはR5基の例は、水素、メチル、エチル、ブチル、ペンチル、ヘキシル、ドデシル、ヘキサデシル、オクタデシルまたはベンジルである。
水性モノマーの逆相懸濁重合を、非水性液体としてのExxsol D40中で行う。水性モノマー相は、水性モノマー、好ましくはアクリルアミド、ジメチルアミノエチルアクリレートのメチルクロリド四級塩からなっていた。安定剤(分散相に対して0.1質量%;メチルメタクリレート、ステアリルメタクリレート、アクリル酸およびメタクリル酸からのコポリマー)を、この連続相に添加し、かつ、この分散されたモノマー溶液中に、開始剤− 2,2’−アゾビス(2−メチルプロピオンアミジン)二塩酸− を混入する。重合後、固体ポリマーを連続相(Exxsol D40)から分離し、これを引き続きクロスフローろ過装置に通してろ過する。
Claims (16)
- 水溶性エチレン性不飽和モノマーまたはモノマーブレンドを含む水溶液の水性モノマービーズを形成すること、および前記モノマーまたはモノマーブレンドを重合することにより、非水性液体中に懸濁されたポリマービーズを形成すること、ポリマービーズを回収すること、および前記非水性液体を清浄化することを含む、ポリマービーズを製造するための逆相懸濁重合法であって、前記方法は、以下:
容器(1)中に前記非水性液体を準備すること、
前記非水性液体中の前記水性モノマーまたはモノマーブレンドからのモノマービーズの懸濁液を形成すること、
重合を開始することにより重合中ビーズを形成すること、
非水性液体中の前記ポリマービーズの懸濁液を前記容器から取り出すこと、および、水溶性または水膨潤性ポリマービーズを前記懸濁液から回収すること、その際、前記非水性液体は粒子を含有する不純物を含むものとする、
および、次いで前記懸濁液からの前記非水性液体を清浄化段階へと移すこと
を含み、その際、前記清浄化段階によって逆相懸濁重合法における使用に適した清浄化された非水性液体を提供し、ここで、前記清浄化段階は、少なくとも1つのろ過ステップにおいて前記非水性液体から粒子を除去することを含むものとし、
ここで、前記清浄化段階はクロスフローろ過ステップを含み、これによって澄明化された非水性液体の流れと濃縮非水性液体の流れとが生成され、その際、前記澄明化された非水性液体は、前記クロスフローろ過ステップの前の前記非水性液体よりも低い粒子濃度を有し、濃縮非水性液体の流れは、前記クロスフローろ過ステップの前の前記非水性液体よりも高い粒子濃度を有する、前記方法。 - 前記清浄化された非水性液体を前記逆相懸濁重合法に再循環させる、請求項1に記載の方法。
- 連続的である、請求項1または2に記載の方法。
- 前記非水性液体を前記容器中にボリューム(2)として準備し、その際、前記ボリュームは少なくとも1つのポリマービーズ排出点(3)と少なくとも1つのモノマー供給点(4)との間に延在するものとし、
かつ、前記水性モノマーまたはモノマーブレンドをオリフィスを通して押出すことによりモノマービーズを形成し、前記モノマービーズを前記ポリマービーズ排出点に向かって流動させ、前記水性モノマービーズの重合を開始し、それによって重合中ビーズを形成し、
その際、前記重合中ビーズは、該重合中ビーズが前記ポリマービーズ排出点に到達した時にはポリマービーズになっているものとする、請求項1から3までのいずれか1項に記載の方法。 - 前記ポリマービーズ排出点で前記容器から取り出された前記ポリマービーズを後重合段階に供する、請求項4に記載の方法。
- 前記ろ過ステップが、以下のいずれか一方:
i)100nm未満、好ましくは50nm未満の平均孔径;または
ii)150,000Da未満、好ましくは60,000Da未満の分画分子量(MWCO)
を有する膜またはろ過媒体の使用を含む、請求項1から5までのいずれか1項に記載の方法。 - 並列する2つ以上の容器(1)中で行う、請求項1から6までのいずれか1項に記載の方法。
- そのように形成されたポリマービーズを粉砕することによりポリマー粉末を生成する、請求項1から7までのいずれか1項に記載の方法。
- 前記濃縮非水性液体の流れを蒸発ステップおよび凝縮ステップに供することにより、凝縮された非水性液体の流れを生成し、
その際、前記清浄化段階はさらに、前記澄明化された非水性液体の流れと前記凝縮された非水性液体の流れとを合一し、かつ前記清浄化された非水性液体を形成することを含む、請求項1から8までのいずれか1項に記載の方法。 - 前記蒸発ステップがワイプトフィルム式蒸発を含む、請求項9に記載の方法。
- 両親媒性安定剤が前記非水性液体中に含まれる、請求項1から10までのいずれか1項に記載の方法。
- 水溶性エチレン性不飽和モノマーまたはモノマーブレンドが、アクリルアミド、メタクリルアミド、N−ビニルピロリドン、2−ヒドロキシエチルアクリレート、アクリル酸(またはその塩)、メタクリル酸(またはその塩)、イタコン酸(またはその塩)、マレイン酸(またはその塩)、2−アクリルアミド−2−プロパンスルホン酸(またはその塩)、ビニルスルホン酸(またはその塩)、アリルスルホン酸(またはその塩)、ジメチルアミノエチルアクリレート(またはその酸塩、またはその第四級アンモニウム塩)、ジメチルアミノエチルメタクリレート(またはその酸塩、またはその第四級アンモニウム塩)、ジメチルアミノプロピルアクリルアミド(またはその酸塩、またはその第四級アンモニウム塩)、ジメチルアミノプロピルメタクリルアミド(またはその酸塩、またはその第四級アンモニウム塩)、および上記のもののいずれかの組み合わせからなる群から選択される少なくとも1種のモノマーを含む、請求項1から11までのいずれか1項に記載の方法。
- 少なくとも1種のモノマーが、化学的触媒法、生物学的触媒法または生物学的方法により製造されたものである、請求項12に記載の方法。
- 前記アクリルアミドが、生物学的触媒法または生物学的方法により製造されたものである、請求項12または13に記載の方法。
- 水溶性エチレン性不飽和モノマーまたはモノマーブレンドを含む水溶液からポリマービーズを製造するための逆相懸濁重合法に適した装置であって、以下:
非水性液体の収容に適した容器(1)、
前記非水性液体中の水性モノマービーズの懸濁液を形成するための手段、
前記非水性液体中の前記ポリマービーズの懸濁液を前記容器から取り出すための手段、
水溶性または水膨潤性ポリマービーズを前記懸濁液から回収するための手段、
少なくとも1つのろ過ステップにより前記非水性液体を清浄化するための手段であって、それにより、前記清浄化された非水性液体が逆相重合法における使用に適したものとなる、前記手段
を含み、ここで、前記清浄化するための手段はクロスフローろ過ユニットを含み、これによって澄明化された非水性液体の流れと濃縮非水性液体の流れとが生成され、その際、前記澄明化された非水性液体は、前記クロスフローろ過ユニットより前の前記非水性液体よりも低い粒子濃度を有し、濃縮非水性液体の流れは、前記クロスフローろ過ユニットより前の前記非水性液体よりも高い粒子濃度を有する、前記装置。 - 以下:
モノマー供給点(4)とポリマービーズ排出点(3)との間に非水性液体のボリューム(2)を収容するのに好適な前記容器(1)、
前記水性モノマーまたはモノマーブレンドの押出しに好適な複数のオリフィス(5)、および
前記水性モノマーまたはモノマーブレンドを、前記オリフィスを通して押出し、それによりモノマービーズを形成するための手段
を含む、請求項15に記載の装置。
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