JP5758810B2 - その場生成されるフッ素化イオノマーの分散した微粒子を使用する水性重合によって製造されるフッ素化イオノマー - Google Patents
その場生成されるフッ素化イオノマーの分散した微粒子を使用する水性重合によって製造されるフッ素化イオノマー Download PDFInfo
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- JP5758810B2 JP5758810B2 JP2011543672A JP2011543672A JP5758810B2 JP 5758810 B2 JP5758810 B2 JP 5758810B2 JP 2011543672 A JP2011543672 A JP 2011543672A JP 2011543672 A JP2011543672 A JP 2011543672A JP 5758810 B2 JP5758810 B2 JP 5758810B2
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- fluorinated
- polymerization
- ionomer
- fluorinated ionomer
- aqueous
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- 229920000554 ionomer Polymers 0.000 title claims description 159
- 238000006116 polymerization reaction Methods 0.000 title claims description 133
- 239000010419 fine particle Substances 0.000 title claims description 14
- 238000011065 in-situ storage Methods 0.000 title description 7
- 238000000034 method Methods 0.000 claims description 88
- 239000002245 particle Substances 0.000 claims description 59
- 239000006185 dispersion Substances 0.000 claims description 47
- 239000000178 monomer Substances 0.000 claims description 34
- 125000003010 ionic group Chemical group 0.000 claims description 29
- 239000003999 initiator Substances 0.000 claims description 26
- -1 sulfonamide anion Chemical class 0.000 claims description 24
- 229910052739 hydrogen Inorganic materials 0.000 claims description 21
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 19
- 239000001257 hydrogen Substances 0.000 claims description 16
- 125000004429 atom Chemical group 0.000 claims description 14
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 12
- 229910052783 alkali metal Inorganic materials 0.000 claims description 10
- 150000007942 carboxylates Chemical class 0.000 claims description 10
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 125000002947 alkylene group Chemical group 0.000 claims description 6
- 125000000129 anionic group Chemical group 0.000 claims description 6
- 230000000379 polymerizing effect Effects 0.000 claims description 6
- 229940124530 sulfonamide Drugs 0.000 claims description 5
- 239000007788 liquid Substances 0.000 claims description 4
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 3
- 239000004094 surface-active agent Substances 0.000 description 46
- 150000003839 salts Chemical class 0.000 description 40
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- 239000002609 medium Substances 0.000 description 30
- 239000002253 acid Substances 0.000 description 29
- 229920000642 polymer Polymers 0.000 description 28
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 27
- 229920002313 fluoropolymer Polymers 0.000 description 26
- 239000004811 fluoropolymer Substances 0.000 description 26
- 125000004432 carbon atom Chemical group C* 0.000 description 24
- 239000007787 solid Substances 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- 239000012736 aqueous medium Substances 0.000 description 13
- 150000001875 compounds Chemical class 0.000 description 13
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- 238000007792 addition Methods 0.000 description 11
- 229920001774 Perfluoroether Polymers 0.000 description 10
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 229910052731 fluorine Inorganic materials 0.000 description 9
- 150000002431 hydrogen Chemical class 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 239000003795 chemical substances by application Substances 0.000 description 8
- 238000002296 dynamic light scattering Methods 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 7
- 150000007513 acids Chemical class 0.000 description 7
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 7
- 239000000155 melt Substances 0.000 description 7
- 238000012546 transfer Methods 0.000 description 7
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 6
- 229910001870 ammonium persulfate Inorganic materials 0.000 description 6
- 229920001577 copolymer Polymers 0.000 description 6
- 239000011737 fluorine Substances 0.000 description 6
- 230000007062 hydrolysis Effects 0.000 description 6
- 238000006460 hydrolysis reaction Methods 0.000 description 6
- 238000005342 ion exchange Methods 0.000 description 6
- 229910052744 lithium Inorganic materials 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 229910052700 potassium Inorganic materials 0.000 description 6
- 239000000523 sample Substances 0.000 description 6
- 229910052708 sodium Inorganic materials 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
- 239000000460 chlorine Substances 0.000 description 5
- 239000012528 membrane Substances 0.000 description 5
- 230000006911 nucleation Effects 0.000 description 5
- 238000010899 nucleation Methods 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- OBTWBSRJZRCYQV-UHFFFAOYSA-N sulfuryl difluoride Chemical group FS(F)(=O)=O OBTWBSRJZRCYQV-UHFFFAOYSA-N 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- 229910019142 PO4 Inorganic materials 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 150000003863 ammonium salts Chemical class 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 239000012986 chain transfer agent Substances 0.000 description 4
- 238000009826 distribution Methods 0.000 description 4
- 125000001153 fluoro group Chemical group F* 0.000 description 4
- 239000000446 fuel Substances 0.000 description 4
- PGFXOWRDDHCDTE-UHFFFAOYSA-N hexafluoropropylene oxide Chemical compound FC(F)(F)C1(F)OC1(F)F PGFXOWRDDHCDTE-UHFFFAOYSA-N 0.000 description 4
- 235000021317 phosphate Nutrition 0.000 description 4
- 239000002243 precursor Substances 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
- 229920001169 thermoplastic Polymers 0.000 description 4
- 239000004416 thermosoftening plastic Substances 0.000 description 4
- KBCYAQVCCAOYEX-UHFFFAOYSA-N 1,1,1,2,3,3-hexafluoro-2-(1,1,2,2,2-pentafluoroethoxy)-3-(1,2,2-trifluoroethenoxy)propane Chemical compound FC(F)=C(F)OC(F)(F)C(F)(C(F)(F)F)OC(F)(F)C(F)(F)F KBCYAQVCCAOYEX-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical class OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 3
- 238000003843 chloralkali process Methods 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 238000007334 copolymerization reaction Methods 0.000 description 3
- 239000002270 dispersing agent Substances 0.000 description 3
- 238000012674 dispersion polymerization Methods 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- 238000010952 in-situ formation Methods 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 3
- JRKICGRDRMAZLK-UHFFFAOYSA-L persulfate group Chemical group S(=O)(=O)([O-])OOS(=O)(=O)[O-] JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 3
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- TXEYQDLBPFQVAA-UHFFFAOYSA-N tetrafluoromethane Chemical compound FC(F)(F)F TXEYQDLBPFQVAA-UHFFFAOYSA-N 0.000 description 3
- 238000013022 venting Methods 0.000 description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
- 239000000908 ammonium hydroxide Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- 230000015271 coagulation Effects 0.000 description 2
- 238000005345 coagulation Methods 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000009792 diffusion process Methods 0.000 description 2
- 238000006471 dimerization reaction Methods 0.000 description 2
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000004945 emulsification Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 230000002209 hydrophobic effect Effects 0.000 description 2
- 239000003014 ion exchange membrane Substances 0.000 description 2
- 238000010128 melt processing Methods 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000002667 nucleating agent Substances 0.000 description 2
- SNGREZUHAYWORS-UHFFFAOYSA-N perfluorooctanoic acid Chemical compound OC(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F SNGREZUHAYWORS-UHFFFAOYSA-N 0.000 description 2
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 150000008054 sulfonate salts Chemical group 0.000 description 2
- 125000000542 sulfonic acid group Chemical group 0.000 description 2
- 238000010998 test method Methods 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- HUPGRQWHZOWFPQ-UHFFFAOYSA-N 1,1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10-henicosafluorododecane Chemical compound CCC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F HUPGRQWHZOWFPQ-UHFFFAOYSA-N 0.000 description 1
- JILAKKYYZPDQBE-UHFFFAOYSA-N 1,1,2,2,3,3,4,4-octafluoro-1,4-diiodobutane Chemical compound FC(F)(I)C(F)(F)C(F)(F)C(F)(F)I JILAKKYYZPDQBE-UHFFFAOYSA-N 0.000 description 1
- BQCIDUSAKPWEOX-UHFFFAOYSA-N 1,1-Difluoroethene Chemical compound FC(F)=C BQCIDUSAKPWEOX-UHFFFAOYSA-N 0.000 description 1
- SUTQSIHGGHVXFK-UHFFFAOYSA-N 1,2,2-trifluoroethenylbenzene Chemical compound FC(F)=C(F)C1=CC=CC=C1 SUTQSIHGGHVXFK-UHFFFAOYSA-N 0.000 description 1
- AOSFMYBATFLTAQ-UHFFFAOYSA-N 1-amino-3-(benzimidazol-1-yl)propan-2-ol Chemical compound C1=CC=C2N(CC(O)CN)C=NC2=C1 AOSFMYBATFLTAQ-UHFFFAOYSA-N 0.000 description 1
- UVHZTXUBKSUXED-UHFFFAOYSA-N 2,3,3,3-tetrafluoro-2-(1,1,2,2,2-pentafluoroethoxy)propanoyl fluoride Chemical compound FC(=O)C(F)(C(F)(F)F)OC(F)(F)C(F)(F)F UVHZTXUBKSUXED-UHFFFAOYSA-N 0.000 description 1
- BCLQALQSEBVVAD-UHFFFAOYSA-N 2,3,3,3-tetrafluoro-2-(1,1,2,2,3,3,3-heptafluoropropoxy)propanoyl fluoride Chemical compound FC(=O)C(F)(C(F)(F)F)OC(F)(F)C(F)(F)C(F)(F)F BCLQALQSEBVVAD-UHFFFAOYSA-N 0.000 description 1
- SELFXCFVPOJKBE-UHFFFAOYSA-N 2-(1-ethenoxypropan-2-yloxy)ethanesulfonic acid Chemical compound C=COCC(C)OCCS(O)(=O)=O SELFXCFVPOJKBE-UHFFFAOYSA-N 0.000 description 1
- PYIMQPQWCZJYNU-UHFFFAOYSA-N 2-propoxypropanoyl fluoride Chemical class CCCOC(C)C(F)=O PYIMQPQWCZJYNU-UHFFFAOYSA-N 0.000 description 1
- JYVYMBONVRBAEJ-UHFFFAOYSA-N 4-methyloct-7-ene-1-sulfonic acid Chemical compound C=CCCC(C)CCCS(O)(=O)=O JYVYMBONVRBAEJ-UHFFFAOYSA-N 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 1
- 229920001410 Microfiber Polymers 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical group 0.000 description 1
- ORBBVPFDROYXQS-UHFFFAOYSA-N ammonium perfluorononanoate Chemical compound N.OC(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F ORBBVPFDROYXQS-UHFFFAOYSA-N 0.000 description 1
- 230000003698 anagen phase Effects 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 238000005311 autocorrelation function Methods 0.000 description 1
- YOALFLHFSFEMLP-UHFFFAOYSA-N azane;2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-pentadecafluorooctanoic acid Chemical compound [NH4+].[O-]C(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F YOALFLHFSFEMLP-UHFFFAOYSA-N 0.000 description 1
- HYGWNUKOUCZBND-UHFFFAOYSA-N azanide Chemical compound [NH2-] HYGWNUKOUCZBND-UHFFFAOYSA-N 0.000 description 1
- 238000010923 batch production Methods 0.000 description 1
- 235000021028 berry Nutrition 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 239000012159 carrier gas Substances 0.000 description 1
- 238000005341 cation exchange Methods 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000003093 cationic surfactant Substances 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 229910001902 chlorine oxide Inorganic materials 0.000 description 1
- QABCGOSYZHCPGN-UHFFFAOYSA-N chloro(dimethyl)silicon Chemical compound C[Si](C)Cl QABCGOSYZHCPGN-UHFFFAOYSA-N 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000000113 differential scanning calorimetry Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000002612 dispersion medium Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005868 electrolysis reaction Methods 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000005188 flotation Methods 0.000 description 1
- 238000003682 fluorination reaction Methods 0.000 description 1
- UODYGZNFOZNALS-UHFFFAOYSA-N fluoro 2-ethenoxyethanesulfonate Chemical compound FOS(=O)(=O)CCOC=C UODYGZNFOZNALS-UHFFFAOYSA-N 0.000 description 1
- 125000003709 fluoroalkyl group Chemical group 0.000 description 1
- XUCNUKMRBVNAPB-UHFFFAOYSA-N fluoroethene Chemical compound FC=C XUCNUKMRBVNAPB-UHFFFAOYSA-N 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000012010 growth Effects 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- HCDGVLDPFQMKDK-UHFFFAOYSA-N hexafluoropropylene Chemical group FC(F)=C(F)C(F)(F)F HCDGVLDPFQMKDK-UHFFFAOYSA-N 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 150000004966 inorganic peroxy acids Chemical class 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 239000003658 microfiber Substances 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- GSWAOPJLTADLTN-UHFFFAOYSA-N oxidanimine Chemical compound [O-][NH3+] GSWAOPJLTADLTN-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- ZWBAMYVPMDSJGQ-UHFFFAOYSA-N perfluoroheptanoic acid Chemical compound OC(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F ZWBAMYVPMDSJGQ-UHFFFAOYSA-N 0.000 description 1
- UZUFPBIDKMEQEQ-UHFFFAOYSA-N perfluorononanoic acid Chemical compound OC(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F UZUFPBIDKMEQEQ-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000005518 polymer electrolyte Substances 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
- 229940001584 sodium metabisulfite Drugs 0.000 description 1
- 235000010262 sodium metabisulphite Nutrition 0.000 description 1
- 239000011973 solid acid Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000010257 thawing Methods 0.000 description 1
- 125000005208 trialkylammonium group Chemical group 0.000 description 1
- 239000011882 ultra-fine particle Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- 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
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US14012208P | 2008-12-23 | 2008-12-23 | |
| US61/140,122 | 2008-12-23 | ||
| PCT/US2009/069377 WO2010075497A1 (en) | 2008-12-23 | 2009-12-23 | Fluorinated ionomer produced by aqueous polymerization using dispersed particulate of fluorinated ionomer produced in situ |
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| JP2012513535A JP2012513535A (ja) | 2012-06-14 |
| JP2012513535A5 JP2012513535A5 (https=) | 2013-02-07 |
| JP5758810B2 true JP5758810B2 (ja) | 2015-08-05 |
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| US (1) | US8436054B2 (https=) |
| EP (1) | EP2367860B1 (https=) |
| JP (1) | JP5758810B2 (https=) |
| CN (1) | CN102264776B (https=) |
| WO (1) | WO2010075497A1 (https=) |
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| WO2014084400A1 (ja) * | 2012-11-30 | 2014-06-05 | ダイキン工業株式会社 | ポリテトラフルオロエチレン水性分散液の製造方法 |
| JP6308949B2 (ja) | 2012-11-30 | 2018-04-11 | ダイキン工業株式会社 | フルオロポリマー水性分散液の製造方法 |
| CN104812780B (zh) * | 2012-11-30 | 2021-10-22 | 大金工业株式会社 | 聚四氟乙烯水性分散液和聚四氟乙烯细粉 |
| JP6225683B2 (ja) * | 2013-05-17 | 2017-11-08 | ダイキン工業株式会社 | フルオロポリマー水性分散液の製造方法 |
| WO2016175502A1 (ko) * | 2015-04-28 | 2016-11-03 | 단국대학교 천안캠퍼스 산학협력단 | 과불소계 이오노머 나노입자 분산액 및 이의 제조방법 |
| JP6974784B2 (ja) | 2018-03-01 | 2021-12-01 | ダイキン工業株式会社 | フルオロポリマーの製造方法 |
| JPWO2019181435A1 (ja) * | 2018-03-22 | 2021-03-18 | 富士フイルム株式会社 | ろ過装置、精製装置、薬液の製造方法 |
| CN117417612A (zh) | 2018-11-19 | 2024-01-19 | 大金工业株式会社 | 组合物和拉伸体 |
| JP7174272B2 (ja) | 2018-11-19 | 2022-11-17 | ダイキン工業株式会社 | 変性ポリテトラフルオロエチレンの製造方法及び組成物 |
| EP3960713A4 (en) | 2019-04-26 | 2023-01-18 | Daikin Industries, Ltd. | Water treatment method and composition |
| CN113728014B (zh) | 2019-04-26 | 2024-07-26 | 大金工业株式会社 | 含氟聚合物水性分散液的制造方法、排水的处理方法和含氟聚合物水性分散液 |
| CN114269840A (zh) | 2019-09-05 | 2022-04-01 | 大金工业株式会社 | 组合物及其制造方法 |
| EP4026856A4 (en) | 2019-09-05 | 2023-09-27 | Daikin Industries, Ltd. | METHOD FOR MANUFACTURING PERFLUOROELASTOMER, AND COMPOSITION |
| CN114651018A (zh) | 2019-11-19 | 2022-06-21 | 大金工业株式会社 | 含氟聚合物的制造方法、聚四氟乙烯的制造方法、全氟弹性体的制造方法和组合物 |
| WO2022107891A1 (ja) | 2020-11-19 | 2022-05-27 | ダイキン工業株式会社 | 含フッ素エラストマー水性分散液の製造方法および組成物 |
| JP7549257B2 (ja) | 2020-11-19 | 2024-09-11 | ダイキン工業株式会社 | パーフルオロエラストマー水性分散液の製造方法、組成物、架橋性組成物および架橋物 |
| WO2022107894A1 (ja) | 2020-11-19 | 2022-05-27 | ダイキン工業株式会社 | ポリテトラフルオロエチレンの製造方法およびポリテトラフルオロエチレンを含有する組成物 |
| EP4306553A4 (en) | 2021-03-10 | 2025-04-30 | Daikin Industries, Ltd. | COATING COMPOSITION, COATING FILM, COATED PRODUCT AND COATED ARTICLE |
| EP4342921A4 (en) | 2021-05-19 | 2025-04-23 | Daikin Industries, Ltd. | Process for producing a fluoropolymer, process for producing polytetrafluoroethylene and composition |
| EP4353759A4 (en) | 2021-06-11 | 2025-06-18 | Daikin Industries, Ltd. | Manufacturing process for aqueous fluorinated elastomer dispersion, composition and aqueous dispersion |
| WO2023277139A1 (ja) | 2021-06-30 | 2023-01-05 | ダイキン工業株式会社 | フルオロポリマー組成物の製造方法およびフルオロポリマー組成物 |
| EP4365211A4 (en) | 2021-06-30 | 2025-07-16 | Daikin Ind Ltd | METHOD FOR PRODUCING A COMPOSITION CONTAINING A HIGH-PURITY FLUOROPOLYMER, AND COMPOSITION CONTAINING A HIGH-PURITY FLUOROPOLYMER |
| JP7791483B2 (ja) | 2022-03-23 | 2025-12-24 | ダイキン工業株式会社 | フルオロポリマーの製造方法および組成物 |
| WO2023210818A1 (ja) | 2022-04-28 | 2023-11-02 | ダイキン工業株式会社 | フッ素ゴムを含有する組成物 |
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| CN119072500A (zh) | 2022-04-28 | 2024-12-03 | 大金工业株式会社 | 含有氟树脂的组合物的制造方法和含有氟树脂的组合物 |
| JP7492186B1 (ja) | 2023-01-18 | 2024-05-29 | ダイキン工業株式会社 | 電気化学デバイス用合剤、電気化学デバイス用合剤シート、電極、及び、電気化学デバイス |
| JP7653042B2 (ja) | 2023-01-18 | 2025-03-28 | ダイキン工業株式会社 | テトラフルオロエチレン系ポリマー組成物、電気化学デバイス用バインダー、電極合剤、電極、及び、二次電池 |
| CN121712810A (zh) | 2023-08-14 | 2026-03-20 | 大金工业株式会社 | 含氟聚合物水性分散液的制造方法和含氟聚合物水性分散液 |
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-
2009
- 2009-12-18 US US12/641,393 patent/US8436054B2/en not_active Expired - Fee Related
- 2009-12-23 WO PCT/US2009/069377 patent/WO2010075497A1/en not_active Ceased
- 2009-12-23 CN CN200980152389.9A patent/CN102264776B/zh not_active Expired - Fee Related
- 2009-12-23 JP JP2011543672A patent/JP5758810B2/ja not_active Expired - Fee Related
- 2009-12-23 EP EP09796264.1A patent/EP2367860B1/en not_active Not-in-force
Also Published As
| Publication number | Publication date |
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| CN102264776B (zh) | 2014-04-30 |
| CN102264776A (zh) | 2011-11-30 |
| JP2012513535A (ja) | 2012-06-14 |
| EP2367860A1 (en) | 2011-09-28 |
| US20100160465A1 (en) | 2010-06-24 |
| EP2367860B1 (en) | 2016-04-27 |
| WO2010075497A1 (en) | 2010-07-01 |
| US8436054B2 (en) | 2013-05-07 |
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