JP2014501298A - 親水性フッ化ビニリデンポリマー - Google Patents
親水性フッ化ビニリデンポリマー Download PDFInfo
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- JP2014501298A JP2014501298A JP2013545177A JP2013545177A JP2014501298A JP 2014501298 A JP2014501298 A JP 2014501298A JP 2013545177 A JP2013545177 A JP 2013545177A JP 2013545177 A JP2013545177 A JP 2013545177A JP 2014501298 A JP2014501298 A JP 2014501298A
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- 229920000642 polymer Polymers 0.000 title claims abstract description 89
- BQCIDUSAKPWEOX-UHFFFAOYSA-N 1,1-Difluoroethene Chemical compound FC(F)=C BQCIDUSAKPWEOX-UHFFFAOYSA-N 0.000 title claims abstract description 41
- 239000000178 monomer Substances 0.000 claims abstract description 53
- 238000000034 method Methods 0.000 claims abstract description 52
- 150000004676 glycans Chemical class 0.000 claims abstract description 29
- 229920001282 polysaccharide Polymers 0.000 claims abstract description 29
- 239000005017 polysaccharide Substances 0.000 claims abstract description 29
- 239000007864 aqueous solution Substances 0.000 claims abstract description 19
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims abstract description 18
- 230000008569 process Effects 0.000 claims abstract description 14
- 229920002313 fluoropolymer Polymers 0.000 claims abstract description 8
- 150000002338 glycosides Chemical group 0.000 claims description 22
- 239000000203 mixture Substances 0.000 claims description 21
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 19
- 239000000725 suspension Substances 0.000 claims description 8
- 239000003381 stabilizer Substances 0.000 claims description 6
- 239000004215 Carbon black (E152) Chemical group 0.000 claims description 4
- 229920002678 cellulose Polymers 0.000 claims description 4
- 239000001913 cellulose Substances 0.000 claims description 4
- 229930195733 hydrocarbon Chemical group 0.000 claims description 4
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 3
- 150000002430 hydrocarbons Chemical group 0.000 claims description 2
- 229930182470 glycoside Natural products 0.000 claims 2
- 238000002360 preparation method Methods 0.000 abstract description 5
- 125000003563 glycoside group Chemical group 0.000 abstract 1
- 230000000379 polymerizing effect Effects 0.000 abstract 1
- 239000012528 membrane Substances 0.000 description 47
- 239000002904 solvent Substances 0.000 description 17
- -1 perfluoroalkyl vinyl ethers Chemical class 0.000 description 14
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- 239000011148 porous material Substances 0.000 description 11
- 229920002981 polyvinylidene fluoride Polymers 0.000 description 10
- 238000004519 manufacturing process Methods 0.000 description 8
- 239000004014 plasticizer Substances 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 238000005266 casting Methods 0.000 description 7
- 238000000605 extraction Methods 0.000 description 7
- 229920003091 Methocel™ Polymers 0.000 description 6
- 239000002033 PVDF binder Substances 0.000 description 6
- 230000005660 hydrophilic surface Effects 0.000 description 6
- 239000003999 initiator Substances 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 238000006116 polymerization reaction Methods 0.000 description 6
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical class OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 5
- 229920003086 cellulose ether Polymers 0.000 description 5
- 125000001033 ether group Chemical group 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 150000003254 radicals Chemical class 0.000 description 5
- BLTXWCKMNMYXEA-UHFFFAOYSA-N 1,1,2-trifluoro-2-(trifluoromethoxy)ethene Chemical compound FC(F)=C(F)OC(F)(F)F BLTXWCKMNMYXEA-UHFFFAOYSA-N 0.000 description 4
- MIZLGWKEZAPEFJ-UHFFFAOYSA-N 1,1,2-trifluoroethene Chemical group FC=C(F)F MIZLGWKEZAPEFJ-UHFFFAOYSA-N 0.000 description 4
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- UUAGAQFQZIEFAH-UHFFFAOYSA-N chlorotrifluoroethylene Chemical group FC(F)=C(F)Cl UUAGAQFQZIEFAH-UHFFFAOYSA-N 0.000 description 4
- HCDGVLDPFQMKDK-UHFFFAOYSA-N hexafluoropropylene Chemical group FC(F)=C(F)C(F)(F)F HCDGVLDPFQMKDK-UHFFFAOYSA-N 0.000 description 4
- 239000012510 hollow fiber Substances 0.000 description 4
- 238000002386 leaching Methods 0.000 description 4
- 229920000728 polyester Polymers 0.000 description 4
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 4
- 150000008505 β-D-glucopyranosides Chemical class 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 230000003993 interaction Effects 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 238000001556 precipitation Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 229920001169 thermoplastic Polymers 0.000 description 3
- 238000000108 ultra-filtration Methods 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- BEQKKZICTDFVMG-UHFFFAOYSA-N 1,2,3,4,6-pentaoxepane-5,7-dione Chemical compound O=C1OOOOC(=O)O1 BEQKKZICTDFVMG-UHFFFAOYSA-N 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- GWZMWHWAWHPNHN-UHFFFAOYSA-N 2-hydroxypropyl prop-2-enoate Chemical compound CC(O)COC(=O)C=C GWZMWHWAWHPNHN-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- NIQCNGHVCWTJSM-UHFFFAOYSA-N Dimethyl phthalate Chemical compound COC(=O)C1=CC=CC=C1C(=O)OC NIQCNGHVCWTJSM-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- ZFOZVQLOBQUTQQ-UHFFFAOYSA-N Tributyl citrate Chemical compound CCCCOC(=O)CC(O)(C(=O)OCCCC)CC(=O)OCCCC ZFOZVQLOBQUTQQ-UHFFFAOYSA-N 0.000 description 2
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 239000012736 aqueous medium Substances 0.000 description 2
- 229940067597 azelate Drugs 0.000 description 2
- BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000001125 extrusion Methods 0.000 description 2
- 125000003709 fluoroalkyl group Chemical group 0.000 description 2
- 230000004907 flux Effects 0.000 description 2
- 150000008131 glucosides Chemical group 0.000 description 2
- 229920001519 homopolymer Polymers 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000012633 leachable Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000001471 micro-filtration Methods 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 238000000465 moulding Methods 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
- 125000005429 oxyalkyl group Chemical group 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 238000011282 treatment Methods 0.000 description 2
- KDGNCLDCOVTOCS-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy propan-2-yl carbonate Chemical compound CC(C)OC(=O)OOC(C)(C)C KDGNCLDCOVTOCS-UHFFFAOYSA-N 0.000 description 1
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 description 1
- RQHGZNBWBKINOY-PLNGDYQASA-N (z)-4-tert-butylperoxy-4-oxobut-2-enoic acid Chemical compound CC(C)(C)OOC(=O)\C=C/C(O)=O RQHGZNBWBKINOY-PLNGDYQASA-N 0.000 description 1
- KHXKESCWFMPTFT-UHFFFAOYSA-N 1,1,1,2,2,3,3-heptafluoro-3-(1,2,2-trifluoroethenoxy)propane Chemical compound FC(F)=C(F)OC(F)(F)C(F)(F)C(F)(F)F KHXKESCWFMPTFT-UHFFFAOYSA-N 0.000 description 1
- HSLFISVKRDQEBY-UHFFFAOYSA-N 1,1-bis(tert-butylperoxy)cyclohexane Chemical compound CC(C)(C)OOC1(OOC(C)(C)C)CCCCC1 HSLFISVKRDQEBY-UHFFFAOYSA-N 0.000 description 1
- 229940058015 1,3-butylene glycol Drugs 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- GOAHRBQLKIZLKG-UHFFFAOYSA-N 1-tert-butylperoxybutane Chemical compound CCCCOOC(C)(C)C GOAHRBQLKIZLKG-UHFFFAOYSA-N 0.000 description 1
- BSXJTDJJVULBTQ-UHFFFAOYSA-N 2,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9,9-heptadecafluorononan-1-ol Chemical compound OCC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F BSXJTDJJVULBTQ-UHFFFAOYSA-N 0.000 description 1
- HFNSTEOEZJBXIF-UHFFFAOYSA-N 2,2,4,5-tetrafluoro-1,3-dioxole Chemical compound FC1=C(F)OC(F)(F)O1 HFNSTEOEZJBXIF-UHFFFAOYSA-N 0.000 description 1
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 1
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 description 1
- WYGWHHGCAGTUCH-UHFFFAOYSA-N 2-[(2-cyano-4-methylpentan-2-yl)diazenyl]-2,4-dimethylpentanenitrile Chemical compound CC(C)CC(C)(C#N)N=NC(C)(C#N)CC(C)C WYGWHHGCAGTUCH-UHFFFAOYSA-N 0.000 description 1
- IIMCDFSTCOSVLK-UHFFFAOYSA-N 2-[(tert-butyldiazenyl)methyl]butanenitrile Chemical compound CCC(C#N)CN=NC(C)(C)C IIMCDFSTCOSVLK-UHFFFAOYSA-N 0.000 description 1
- JJRDRFZYKKFYMO-UHFFFAOYSA-N 2-methyl-2-(2-methylbutan-2-ylperoxy)butane Chemical compound CCC(C)(C)OOC(C)(C)CC JJRDRFZYKKFYMO-UHFFFAOYSA-N 0.000 description 1
- GTJOHISYCKPIMT-UHFFFAOYSA-N 2-methylundecane Chemical compound CCCCCCCCCC(C)C GTJOHISYCKPIMT-UHFFFAOYSA-N 0.000 description 1
- RTANHMOFHGSZQO-UHFFFAOYSA-N 4-methoxy-2,4-dimethylpentanenitrile Chemical compound COC(C)(C)CC(C)C#N RTANHMOFHGSZQO-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- WWXUGNUFCNYMFK-UHFFFAOYSA-N Acetyl citrate Chemical compound CC(=O)OC(=O)CC(O)(C(O)=O)CC(O)=O WWXUGNUFCNYMFK-UHFFFAOYSA-N 0.000 description 1
- QZCLKYGREBVARF-UHFFFAOYSA-N Acetyl tributyl citrate Chemical compound CCCCOC(=O)CC(C(=O)OCCCC)(OC(C)=O)CC(=O)OCCCC QZCLKYGREBVARF-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 239000004804 Butyryltrihexylcitrate Substances 0.000 description 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 1
- ZVFDTKUVRCTHQE-UHFFFAOYSA-N Diisodecyl phthalate Chemical compound CC(C)CCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC(C)C ZVFDTKUVRCTHQE-UHFFFAOYSA-N 0.000 description 1
- SGVYKUFIHHTIFL-UHFFFAOYSA-N Isobutylhexyl Natural products CCCCCCCC(C)C SGVYKUFIHHTIFL-UHFFFAOYSA-N 0.000 description 1
- YIVJZNGAASQVEM-UHFFFAOYSA-N Lauroyl peroxide Chemical compound CCCCCCCCCCCC(=O)OOC(=O)CCCCCCCCCCC YIVJZNGAASQVEM-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
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- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- DOOTYTYQINUNNV-UHFFFAOYSA-N Triethyl citrate Chemical compound CCOC(=O)CC(O)(C(=O)OCC)CC(=O)OCC DOOTYTYQINUNNV-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- CSCPPACGZOOCGX-WFGJKAKNSA-N acetone d6 Chemical compound [2H]C([2H])([2H])C(=O)C([2H])([2H])[2H] CSCPPACGZOOCGX-WFGJKAKNSA-N 0.000 description 1
- JEAIVVDKUUARLF-UHFFFAOYSA-N acetyloxycarbonylperoxycarbonyl acetate Chemical compound CC(=O)OC(=O)OOC(=O)OC(C)=O JEAIVVDKUUARLF-UHFFFAOYSA-N 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
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- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 235000019437 butane-1,3-diol Nutrition 0.000 description 1
- KKPMZLPPEXRJOM-UHFFFAOYSA-N butane-1,3-diol;hexanedioic acid Chemical compound CC(O)CCO.OC(=O)CCCCC(O)=O KKPMZLPPEXRJOM-UHFFFAOYSA-N 0.000 description 1
- 150000001719 carbohydrate derivatives Chemical class 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
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- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical class OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 1
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- JQGRPPCZXQJUAF-UHFFFAOYSA-N decanedioic acid;propane-1,2-diol Chemical compound CC(O)CO.OC(=O)CCCCCCCCC(O)=O JQGRPPCZXQJUAF-UHFFFAOYSA-N 0.000 description 1
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- HBGGXOJOCNVPFY-UHFFFAOYSA-N diisononyl phthalate Chemical compound CC(C)CCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCC(C)C HBGGXOJOCNVPFY-UHFFFAOYSA-N 0.000 description 1
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- CWINGZLCRSDKCL-UHFFFAOYSA-N ethoxycarbonyloxy ethyl carbonate Chemical compound CCOC(=O)OOC(=O)OCC CWINGZLCRSDKCL-UHFFFAOYSA-N 0.000 description 1
- DUDCYUDPBRJVLG-UHFFFAOYSA-N ethoxyethane methyl 2-methylprop-2-enoate Chemical compound CCOCC.COC(=O)C(C)=C DUDCYUDPBRJVLG-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
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- 125000001153 fluoro group Chemical group F* 0.000 description 1
- XUCNUKMRBVNAPB-UHFFFAOYSA-N fluoroethene Chemical compound FC=C XUCNUKMRBVNAPB-UHFFFAOYSA-N 0.000 description 1
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- 238000001631 haemodialysis Methods 0.000 description 1
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- 230000000322 hemodialysis Effects 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- MEBJLVMIIRFIJS-UHFFFAOYSA-N hexanedioic acid;propane-1,2-diol Chemical compound CC(O)CO.OC(=O)CCCCC(O)=O MEBJLVMIIRFIJS-UHFFFAOYSA-N 0.000 description 1
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- 125000001400 nonyl 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])[H] 0.000 description 1
- SRSFOMHQIATOFV-UHFFFAOYSA-N octanoyl octaneperoxoate Chemical compound CCCCCCCC(=O)OOC(=O)CCCCCCC SRSFOMHQIATOFV-UHFFFAOYSA-N 0.000 description 1
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- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- RYVMUASDIZQXAA-UHFFFAOYSA-N pyranoside Natural products O1C2(OCC(C)C(OC3C(C(O)C(O)C(CO)O3)O)C2)C(C)C(C2(CCC3C4(C)CC5O)C)C1CC2C3CC=C4CC5OC(C(C1O)O)OC(CO)C1OC(C1OC2C(C(OC3C(C(O)C(O)C(CO)O3)O)C(O)C(CO)O2)O)OC(CO)C(O)C1OC1OCC(O)C(O)C1O RYVMUASDIZQXAA-UHFFFAOYSA-N 0.000 description 1
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- 238000000926 separation method Methods 0.000 description 1
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- SWAXTRYEYUTSAP-UHFFFAOYSA-N tert-butyl ethaneperoxoate Chemical compound CC(=O)OOC(C)(C)C SWAXTRYEYUTSAP-UHFFFAOYSA-N 0.000 description 1
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- APVVRLGIFCYZHJ-UHFFFAOYSA-N trioctyl 2-hydroxypropane-1,2,3-tricarboxylate Chemical compound CCCCCCCCOC(=O)CC(O)(C(=O)OCCCCCCCC)CC(=O)OCCCCCCCC APVVRLGIFCYZHJ-UHFFFAOYSA-N 0.000 description 1
- 238000001132 ultrasonic dispersion Methods 0.000 description 1
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Classifications
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F259/00—Macromolecular compounds obtained by polymerising monomers on to polymers of halogen containing monomers as defined in group C08F14/00
- C08F259/08—Macromolecular compounds obtained by polymerising monomers on to polymers of halogen containing monomers as defined in group C08F14/00 on to polymers containing fluorine
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F14/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen
- C08F14/18—Monomers containing fluorine
- C08F14/22—Vinylidene fluoride
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- B01D—SEPARATION
- B01D71/00—Semi-permeable membranes for separation processes or apparatus characterised by the material; Manufacturing processes specially adapted therefor
- B01D71/06—Organic material
- B01D71/30—Polyalkenyl halides
- B01D71/32—Polyalkenyl halides containing fluorine atoms
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D71/00—Semi-permeable membranes for separation processes or apparatus characterised by the material; Manufacturing processes specially adapted therefor
- B01D71/06—Organic material
- B01D71/76—Macromolecular material not specifically provided for in a single one of groups B01D71/08 - B01D71/74
- B01D71/78—Graft polymers
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- C—CHEMISTRY; METALLURGY
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- C08F214/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen
- C08F214/18—Monomers containing fluorine
- C08F214/22—Vinylidene fluoride
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- C08F251/00—Macromolecular compounds obtained by polymerising monomers on to polysaccharides or derivatives thereof
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- C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
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- C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
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Abstract
Description
−フッ化ビニリデン(VDF)、
−任意選択で、1種以上の他のフッ素化モノマー[モノマー(F)]、および
−任意選択で、1種以上の(メタ)アクリルモノマー[モノマー(MA)]
を、少なくとも1種の多糖類誘導体[誘導体(P)]の存在下で重合させる工程を含み、前記多糖類誘導体は、2重量%の濃度の水溶液中20℃でASTM D445に従って測定して、15mPa×s未満の動的粘度を有する方法を提供することによって、
ならびに次に、上に定義されたとおりの新規なポリマー(F)を提供することによってもたらされる。
(i)C2〜C8フルオロオレフィン、例えば、トリフルオロエチレン(TrFE)、テトラフルオロエチレン(TFE)およびヘキサフルオロプロピレン(HFP);
(ii)式CH2=CH−Rf0(式中、Rf0は、C2〜C6パーフルオロアルキル基である)のパーフルオロアルキルエチレン;
(iii)クロロ−および/またはブロモ−および/またはヨード−C2〜C6フルオロオレフィン、例えば、クロロトリフルオロエチレン(CTFE);
(iv)式CF2=CFORf1(式中、Rf1は、C1〜C6パーフルオロアルキル基である)のパーフルオロアルキルビニルエーテル、例えば、パーフルオロメチルビニルエーテル(PMVE)およびパーフルオロプロピルビニルエーテル(PPVE);
(v)式CF2=CFOX0(式中、X0は、1個以上のエーテル基を有するC1〜C12オキシアルキル基またはC1〜C12(パー)フルオロオキシアルキル基、例えば、パーフルオロ−2−プロポキシ−プロピル基である)の(パー)フルオロオキシアルキルビニルエーテル;
(vi)式CF2=CFOCF2ORf2(式中、Rf2は、C1〜C6(パー)フルオロアルキル基、例えば、−CF3、−C2F5、−C3F7、または1個以上のエーテル基を有するC1〜C6(パー)フルオロオキシアルキル基、例えば、−C2F5−O−CF3である)の(パー)フルオロアルキルビニルエーテル;
(vii)式CF2=CFOY0(式中、Y0は、C1〜C12アルキル基または(パー)フルオロアルキル基、1個以上のエーテル基を有するC1〜C12オキシアルキル基およびC1〜C12(パー)フルオロオキシアルキル基から選択され、Y0は、カルボン酸またはスルホン酸基をその酸、酸ハロゲン化物または塩の形態で含む)の官能性(パー)フルオロオキシアルキルビニルエーテル;
(viii)フルオロジオキソール、特にパーフルオロジオキソール;
(ix)フッ化ビニル
が含まれる。
−R1、R2およびR3は、互いに等しいかまたは異なり、水素原子およびC1〜C3炭化水素基から独立して選択され;
−ROHは、水素原子、または少なくとも1個のヒドロキシル基を含むC1〜C5炭化水素部分を表す)
に従う。
−R’1およびR’2は、互いに等しいかまたは異なり、水素原子およびC1〜C3炭化水素基から独立して選択され、好ましくはR’1およびR’2は、水素原子であり;
−R’3は、水素原子であり、
−R’OHは、水素原子、または少なくとも1個のヒドロキシル基を含むC1〜C5炭化水素部分を表す)
に従う。
−式:
−式:
−式:
−およびそれらの混合物
から選択される。
−フッ化ビニリデン(VDF)に由来する繰り返し単位、任意選択で、上に定義されたとおりの1種以上の他のフッ素化モノマー[モノマー(F)]に由来する繰り返し単位、および任意選択で、上に定義されたとおりの1種以上の(メタ)アクリルモノマー[モノマー(MA)]に由来する繰り返し単位を含む主鎖、ならびに
−前記主鎖にグラフト化された少なくとも1つの側鎖であって、前記グラフト化側鎖は、上に定義されたとおりの1個以上のグリコシド繰り返し単位を含む側鎖
を含む。
−VDFに由来する繰り返し単位、任意選択で、上に定義されたとおりの1種以上の他のフッ素化モノマー[モノマー(F)]に由来する繰り返し単位、および任意選択で、上に定義されたとおりの1種以上の(メタ)アクリルモノマー[モノマー(MA)]に由来する繰り返し単位を含む主鎖、ならびに
−前記主鎖にグラフト化された少なくとも1つの側鎖であって、前記グラフト化側鎖は、β−グリコシド結合によって互いに連結された上に記載されたとおりの式(III−b)の1個以上のβ−D−グルコピラノシドを含む側鎖
を含む。
−VDFに由来する繰り返し単位、任意選択で、上に定義されたとおりの1種以上の他のフッ素化モノマー[モノマー(F)]に由来する繰り返し単位、および任意選択で、上に定義されたとおりの1種以上の(メタ)アクリルモノマー[モノマー(MA)]に由来する繰り返し単位を含む主鎖、ならびに
−前記主鎖にグラフト化された少なくとも1つの側鎖であって、前記グラフト化側鎖は、ポリマー(F)の主鎖におけるVDF繰り返し単位の水素原子の全量に対して、上に記載されたとおりの式(III−b)の1つ以上のβ−D−グルコピラノシドの水素原子を少なくとも65ppm含み、前記β−D−グルコピラノシドは、β−グリコシド結合によって互いに連結されている側鎖
を含む。
ポリマー中のグラフト化グリコシド繰り返し単位の量は、1H−NMR技術によって決定した。予めエタノールで洗浄し、乾燥させた約20mgのポリマー粉末を、0.6mlのヘキサジュウテロアセトン(hexadeuteroacetone)中に溶解させ、次いで、NMR分光計で分析した。1H−NMRスペクトルにより、約3.5〜3.6ppmにおけるグリコシド繰り返し単位の−OCH3および−CH−に関連するシグナル、ならびに約2.5および3ppmにおけるVDF繰り返し単位の−CH2−部分に関連するシグナルが明らかになった。グラフト化グリコシド繰り返し単位に属する水素含有量(ppm単位)は、ポリマーの主鎖中のVDF繰り返し単位の水素含有量に対して決定した(以下の表2を参照)。
4gのポリマー粉末を、ビーカーグラス中40mlの脱塩水中に磁気撹拌によって1分間分散させた。超音波分散1分後、懸濁液を一晩静置して、2相に分離させた。この2相を分離させ、乾燥させ、秤量した。これらの乾燥した2相の重量割合を、測定した(以下の表2参照)。本発明のポリマー(F)が、前記ポリマー(F)の1個以上の側鎖中の低レベルのグラフト化グリコシド単位においてさえも、満足な親水性表面特性を示すために、ビーカーの底部における乾燥相の重量割合が、乾燥した2相の合計重量に対して少なくとも50重量%であることが必須である。
ポリマー(F)の製造
880rpmの速度で回転するインペラーを備えた4リットルの反応器中に、その後に2050gの脱塩水、以下の表1に詳述したとおりの量のMETHOCEL(商標)K3セルロースエーテル、および任意選択で、METHOCEL(商標)K100を導入した。次いで、反応器を、その温度を14℃に維持しながら、繰り返して、排気しそして窒素(1バール)でバージした。次いで、24.5gのジエチルカーボネート/kgの供給VDF、tert−アミルパーピバレートラジカル開始剤のイソドデカン中75重量%溶液の1g/kgの供給VDF、および1346gのVDFを反応器に導入した。次いで、52℃の設定点温度が達成されるまで、反応器を徐々に加熱し、これは、120バールの圧力に相当した。水を供給することによって、圧力を重合実験全体の間120バールに等しく一定に保った。VDFの約80〜90%の変換後、大気圧に達するまで懸濁液を脱気することによって重合を止めた。次いで、ポリマーをろ過により収集し、脱塩水で洗浄し、50℃でオーブン乾燥させた。ジメチルホルムアミド中25℃で0.15l/gの固有粘度および約100〜120μm(D50)の粒径を有するポリマーが得られた。
VDFホモポリマーの製造
本発明による実施例1〜実施例3に詳述したものと同じ手順に従ったが、2重量%の濃度の水溶液中20℃でASTM D445に従って測定して、15mPa×s未満の動的粘度を有する多糖類誘導体は用いることはしなかった(以下の表1参照)。
Claims (10)
- 1個以上のグリコシド繰り返し単位を含む少なくとも1つのグラフト化側鎖を含むグラフト化フッ素化ポリマー[ポリマー(F)]の製造方法であって、前記方法は、
−フッ化ビニリデン(VDF)、
−任意選択で、1種以上の他のフッ素化モノマー[モノマー(F)]、および
−任意選択で、1種以上の(メタ)アクリルモノマー[モノマー(MA)]
を、少なくとも1種の多糖類誘導体[誘導体(P)]の存在下で重合させる工程を含み、前記多糖類誘導体は、2重量%の濃度の水溶液中20℃でASTM D445に従って測定して、多くとも12mPa×sの動的粘度を有する、方法。 - 前記多糖類誘導体が、グリコシド結合によって互いに連結されたD−グルコピラノシドから選択されるグリコシド単位を繰り返し単位として含む、請求項1に記載の方法。
- 前記多糖類誘導体が、2重量%の濃度の水溶液中20℃でASTM D445に従って測定して、2〜10mPa×sの間に含まれる動的粘度を有する、請求項1〜3のいずれか一項に記載の方法。
- 1種以上の懸濁液安定剤が用いられる、請求項1〜4のいずれか一項に記載の方法。
- −フッ化ビニリデン(VDF)に由来する繰り返し単位、任意選択で、1種以上の他のフッ素化モノマー[モノマー(F)]に由来する繰り返し単位、および任意選択で、1種以上の(メタ)アクリルモノマー[モノマー(MA)]に由来する繰り返し単位を含む主鎖、ならびに
−前記主鎖にグラフト化された少なくとも1つの側鎖であって、1個以上のグリコシド繰り返し単位を含む側鎖
を含むフッ素化ポリマー[ポリマー(F)]。 - 前記ポリマー(F)の主鎖中のVDF繰り返し単位の水素原子の全量に対して、ポリマー(F)の少なくとも1つのグラフト化側鎖中の1個以上のグリコシド繰り返し単位の水素原子を少なくとも40ppm、好ましくは少なくとも50ppm、より好ましくは少なくとも60ppm含む、請求項6に記載のポリマー。
- 少なくとも1つの側鎖が、β−グリコシド結合によって互いに連結された1つ以上の請求項3に定義された式(III−b)のβ−D−グルコピラノシドを含む、請求項6または7に記載のポリマー。
- 前記請求項6〜8のいずれか一項に記載のポリマーおよび少なくとも1種のVDFポリマーを含む組成物。
- 前記請求項6〜8のいずれか一項に記載のポリマーまたは請求項9に記載の組成物を含む親水性膜。
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PCT/EP2011/072508 WO2012084580A1 (en) | 2010-12-22 | 2011-12-13 | Hydrophilic vinylidene fluoride polymers |
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JP2017527678A (ja) * | 2014-09-17 | 2017-09-21 | ソルベイ スペシャルティ ポリマーズ イタリー エス.ピー.エー. | フッ化ビニリデンポリマー |
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AU2013361727B9 (en) * | 2012-12-21 | 2017-11-09 | Solvay Specialty Polymers Italy S.P.A. | Hydrophilic fluoropolymer |
CN108939939B (zh) * | 2014-07-08 | 2021-02-09 | 天津工业大学 | 一种抗凝血改性pvdf平板分离膜 |
KR101772808B1 (ko) * | 2016-03-18 | 2017-08-30 | 연세대학교 산학협력단 | Tsv 테스트 및 분석 회로 및 테스트 방법 |
US11312803B2 (en) * | 2016-12-22 | 2022-04-26 | Solvay Specialty Polymers Italy S.P.A. | Vinylidene fluoride polymer |
CN108823676A (zh) * | 2018-05-25 | 2018-11-16 | 上海城市水资源开发利用国家工程中心有限公司 | 一种基于静电纺丝技术制备超亲水pvdf复合纳米纤维的方法 |
WO2022229361A1 (en) * | 2021-04-29 | 2022-11-03 | Solvay Specialty Polymers Italy S.P.A. | Pvdf fine powders |
WO2023117971A1 (en) | 2021-12-23 | 2023-06-29 | Solvay Specialty Polymers Italy S.P.A. | Method for the purification of vinylidene fluoride polymers |
US11643486B1 (en) * | 2022-06-08 | 2023-05-09 | Arkema Inc. | Non-linear vinylidene fluoride copolymers |
CN114989344B (zh) * | 2022-06-14 | 2023-09-19 | 万华化学集团股份有限公司 | 一种偏氟乙烯共聚物及其制备方法和在锂离子电池中的应用 |
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EP2655452B1 (en) | 2017-02-22 |
KR20140000308A (ko) | 2014-01-02 |
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