JP5371770B2 - アミンオキシド界面活性剤で安定化された水性フルオロポリマー分散系および凝固フルオロポリマー樹脂の製造方法 - Google Patents
アミンオキシド界面活性剤で安定化された水性フルオロポリマー分散系および凝固フルオロポリマー樹脂の製造方法 Download PDFInfo
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- JP5371770B2 JP5371770B2 JP2009540261A JP2009540261A JP5371770B2 JP 5371770 B2 JP5371770 B2 JP 5371770B2 JP 2009540261 A JP2009540261 A JP 2009540261A JP 2009540261 A JP2009540261 A JP 2009540261A JP 5371770 B2 JP5371770 B2 JP 5371770B2
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- 239000006185 dispersion Substances 0.000 title claims description 180
- 229920002313 fluoropolymer Polymers 0.000 title claims description 130
- 239000004811 fluoropolymer Substances 0.000 title claims description 130
- 239000004094 surface-active agent Substances 0.000 title claims description 55
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- 125000004432 carbon atom Chemical group C* 0.000 claims description 42
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 38
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 23
- -1 N-oxylamino group Chemical group 0.000 claims description 22
- 125000004122 cyclic group Chemical group 0.000 claims description 21
- 229920006395 saturated elastomer Polymers 0.000 claims description 21
- 229910052736 halogen Inorganic materials 0.000 claims description 18
- JSPLKZUTYZBBKA-UHFFFAOYSA-N trioxidane Chemical group OOO JSPLKZUTYZBBKA-UHFFFAOYSA-N 0.000 claims description 18
- 125000005843 halogen group Chemical group 0.000 claims description 17
- 239000012445 acidic reagent Substances 0.000 claims description 16
- 125000000129 anionic group Chemical group 0.000 claims description 15
- 239000012736 aqueous medium Substances 0.000 claims description 13
- 239000000126 substance Substances 0.000 claims description 9
- 150000002367 halogens Chemical class 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
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- 229920000642 polymer Polymers 0.000 description 28
- 239000007787 solid Substances 0.000 description 26
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 23
- 239000000178 monomer Substances 0.000 description 21
- 238000005345 coagulation Methods 0.000 description 19
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- 125000000217 alkyl group Chemical group 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 239000003957 anion exchange resin Substances 0.000 description 13
- 230000015271 coagulation Effects 0.000 description 13
- 239000000499 gel Substances 0.000 description 11
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 10
- 238000005349 anion exchange Methods 0.000 description 9
- 239000003456 ion exchange resin Substances 0.000 description 9
- 229920003303 ion-exchange polymer Polymers 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 238000006116 polymerization reaction Methods 0.000 description 9
- 239000002253 acid Substances 0.000 description 8
- HCDGVLDPFQMKDK-UHFFFAOYSA-N hexafluoropropylene Chemical group FC(F)=C(F)C(F)(F)F HCDGVLDPFQMKDK-UHFFFAOYSA-N 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000003999 initiator Substances 0.000 description 7
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 6
- JNGWKQJZIUZUPR-UHFFFAOYSA-N [3-(dodecanoylamino)propyl](hydroxy)dimethylammonium Chemical compound CCCCCCCCCCCC(=O)NCCC[N+](C)(C)[O-] JNGWKQJZIUZUPR-UHFFFAOYSA-N 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 239000000155 melt Substances 0.000 description 6
- 229910017604 nitric acid Inorganic materials 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- UUAGAQFQZIEFAH-UHFFFAOYSA-N chlorotrifluoroethylene Chemical group FC(F)=C(F)Cl UUAGAQFQZIEFAH-UHFFFAOYSA-N 0.000 description 5
- 238000012674 dispersion polymerization Methods 0.000 description 5
- 229920001519 homopolymer Polymers 0.000 description 5
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- 238000012546 transfer Methods 0.000 description 5
- GVEUEBXMTMZVSD-UHFFFAOYSA-N 3,3,4,4,5,5,6,6,6-nonafluorohex-1-ene Chemical group FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C=C GVEUEBXMTMZVSD-UHFFFAOYSA-N 0.000 description 4
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 235000011114 ammonium hydroxide Nutrition 0.000 description 4
- 239000011324 bead Substances 0.000 description 4
- 239000000945 filler Substances 0.000 description 4
- 229910052731 fluorine Inorganic materials 0.000 description 4
- 125000001153 fluoro group Chemical group F* 0.000 description 4
- 230000005484 gravity Effects 0.000 description 4
- 239000000314 lubricant Substances 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 239000002736 nonionic surfactant Substances 0.000 description 4
- 239000000049 pigment Substances 0.000 description 4
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- 238000012545 processing Methods 0.000 description 4
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- 230000008023 solidification Effects 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 4
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 3
- 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 3
- 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 3
- BQCIDUSAKPWEOX-UHFFFAOYSA-N 1,1-Difluoroethene Chemical compound FC(F)=C BQCIDUSAKPWEOX-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 229910001347 Stellite Inorganic materials 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 239000000908 ammonium hydroxide Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
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- 238000001035 drying Methods 0.000 description 3
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- 229910052500 inorganic mineral Inorganic materials 0.000 description 3
- 239000011707 mineral Substances 0.000 description 3
- 238000002156 mixing Methods 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
- 229920003217 poly(methylsilsesquioxane) Polymers 0.000 description 3
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 3
- 125000001453 quaternary ammonium group Chemical group 0.000 description 3
- 150000003839 salts Chemical group 0.000 description 3
- 230000006641 stabilisation Effects 0.000 description 3
- 238000011105 stabilization Methods 0.000 description 3
- YSYRISKCBOPJRG-UHFFFAOYSA-N 4,5-difluoro-2,2-bis(trifluoromethyl)-1,3-dioxole Chemical compound FC1=C(F)OC(C(F)(F)F)(C(F)(F)F)O1 YSYRISKCBOPJRG-UHFFFAOYSA-N 0.000 description 2
- MKTOIPPVFPJEQO-UHFFFAOYSA-N 4-(3-carboxypropanoylperoxy)-4-oxobutanoic acid Chemical compound OC(=O)CCC(=O)OOC(=O)CCC(O)=O MKTOIPPVFPJEQO-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-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
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000004677 Nylon Substances 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 238000013019 agitation Methods 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 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
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 229920001429 chelating resin Polymers 0.000 description 2
- AHICWQREWHDHHF-UHFFFAOYSA-N chromium;cobalt;iron;manganese;methane;molybdenum;nickel;silicon;tungsten Chemical compound C.[Si].[Cr].[Mn].[Fe].[Co].[Ni].[Mo].[W] AHICWQREWHDHHF-UHFFFAOYSA-N 0.000 description 2
- 230000001112 coagulating effect Effects 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 230000007797 corrosion Effects 0.000 description 2
- 238000005260 corrosion Methods 0.000 description 2
- 238000010828 elution Methods 0.000 description 2
- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- XUCNUKMRBVNAPB-UHFFFAOYSA-N fluoroethene Chemical compound FC=C XUCNUKMRBVNAPB-UHFFFAOYSA-N 0.000 description 2
- 239000008240 homogeneous mixture Substances 0.000 description 2
- 230000002209 hydrophobic effect Effects 0.000 description 2
- 238000005342 ion exchange Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000005259 measurement 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
- 229920001778 nylon Polymers 0.000 description 2
- 239000012188 paraffin wax Substances 0.000 description 2
- 229920002493 poly(chlorotrifluoroethylene) Polymers 0.000 description 2
- 239000005023 polychlorotrifluoroethylene (PCTFE) polymer Substances 0.000 description 2
- 230000002028 premature Effects 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- MKWYFZFMAMBPQK-UHFFFAOYSA-J sodium feredetate Chemical compound [Na+].[Fe+3].[O-]C(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O MKWYFZFMAMBPQK-UHFFFAOYSA-J 0.000 description 2
- 238000001179 sorption measurement Methods 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 239000001384 succinic acid Substances 0.000 description 2
- 238000010998 test method Methods 0.000 description 2
- MIZLGWKEZAPEFJ-UHFFFAOYSA-N 1,1,2-trifluoroethene Chemical group FC=C(F)F MIZLGWKEZAPEFJ-UHFFFAOYSA-N 0.000 description 1
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-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
- JMGNVALALWCTLC-UHFFFAOYSA-N 1-fluoro-2-(2-fluoroethenoxy)ethene Chemical compound FC=COC=CF JMGNVALALWCTLC-UHFFFAOYSA-N 0.000 description 1
- QMIWYOZFFSLIAK-UHFFFAOYSA-N 3,3,3-trifluoro-2-(trifluoromethyl)prop-1-ene Chemical group FC(F)(F)C(=C)C(F)(F)F QMIWYOZFFSLIAK-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- FGEGZNORXGGFML-UHFFFAOYSA-N C(C)C=COF Chemical compound C(C)C=COF FGEGZNORXGGFML-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- UNPLRYRWJLTVAE-UHFFFAOYSA-N Cloperastine hydrochloride Chemical compound Cl.C1=CC(Cl)=CC=C1C(C=1C=CC=CC=1)OCCN1CCCCC1 UNPLRYRWJLTVAE-UHFFFAOYSA-N 0.000 description 1
- 206010053567 Coagulopathies Diseases 0.000 description 1
- 229920001780 ECTFE Polymers 0.000 description 1
- VTLYFUHAOXGGBS-UHFFFAOYSA-N Fe3+ Chemical compound [Fe+3] VTLYFUHAOXGGBS-UHFFFAOYSA-N 0.000 description 1
- 241000300617 Isotes Species 0.000 description 1
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical group CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical group [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000274 adsorptive effect Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910001870 ammonium persulfate Inorganic materials 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 229910052786 argon Inorganic materials 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
- HDDMREWZGLZQMX-UHFFFAOYSA-N azanium;carbonofluoridate Chemical class [NH4+].[O-]C(F)=O HDDMREWZGLZQMX-UHFFFAOYSA-N 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 235000021028 berry Nutrition 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000012159 carrier gas Substances 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- QABCGOSYZHCPGN-UHFFFAOYSA-N chloro(dimethyl)silicon Chemical compound C[Si](C)Cl QABCGOSYZHCPGN-UHFFFAOYSA-N 0.000 description 1
- 230000035602 clotting Effects 0.000 description 1
- 239000008199 coating composition Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000000498 cooling water Substances 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 238000007720 emulsion polymerization reaction Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 229920000840 ethylene tetrafluoroethylene copolymer Polymers 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000003682 fluorination reaction Methods 0.000 description 1
- 125000003709 fluoroalkyl group Chemical group 0.000 description 1
- 230000014509 gene expression Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 230000016507 interphase Effects 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- FOKCKXCUQFKNLD-UHFFFAOYSA-N pent-1-enyl hypofluorite Chemical compound C(CC)C=COF FOKCKXCUQFKNLD-UHFFFAOYSA-N 0.000 description 1
- 125000005010 perfluoroalkyl group Chemical group 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
- YVBBRRALBYAZBM-UHFFFAOYSA-N perfluorooctane Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F YVBBRRALBYAZBM-UHFFFAOYSA-N 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 238000005185 salting out Methods 0.000 description 1
- 150000003335 secondary amines Chemical class 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
- 239000000243 solution Substances 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 230000003797 telogen phase Effects 0.000 description 1
- 150000003512 tertiary amines Chemical group 0.000 description 1
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical group CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
- 238000000108 ultra-filtration Methods 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/32—Compounds containing nitrogen bound to oxygen
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Processes Of Treating Macromolecular Substances (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US87275006P | 2006-12-04 | 2006-12-04 | |
| US60/872,750 | 2006-12-04 | ||
| PCT/US2007/024835 WO2008070079A1 (en) | 2006-12-04 | 2007-12-04 | Aqueous fluoropolymer dispersion stabilized with amine oxide surfactant and process for making coagulated fluoropolymer resin |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2010511777A JP2010511777A (ja) | 2010-04-15 |
| JP2010511777A5 JP2010511777A5 (OSRAM) | 2011-01-13 |
| JP5371770B2 true JP5371770B2 (ja) | 2013-12-18 |
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| JP2009540261A Active JP5371770B2 (ja) | 2006-12-04 | 2007-12-04 | アミンオキシド界面活性剤で安定化された水性フルオロポリマー分散系および凝固フルオロポリマー樹脂の製造方法 |
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| EP (1) | EP2094784B1 (OSRAM) |
| JP (1) | JP5371770B2 (OSRAM) |
| CN (1) | CN101541883B (OSRAM) |
| AT (1) | ATE530603T1 (OSRAM) |
| WO (1) | WO2008070079A1 (OSRAM) |
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|---|---|---|---|---|
| US20080264864A1 (en) | 2007-04-27 | 2008-10-30 | 3M Innovative Properties Company | PROCESS FOR REMOVING FLUORINATED EMULSIFIER FROM FLUOROPOLMER DISPERSIONS USING AN ANION-EXCHANGE RESIN AND A pH-DEPENDENT SURFACTANT AND FLUOROPOLYMER DISPERSIONS CONTAINING A pH-DEPENDENT SURFACTANT |
| WO2012067936A2 (en) | 2010-11-18 | 2012-05-24 | 3M Innovative Properties Company | Method of coagulating an amorphous fluoropolymer latex |
| CN103865081B (zh) * | 2014-03-19 | 2016-01-27 | 四川大学 | 高分子量聚四氟乙烯微粉的制备方法 |
| CN104744710B (zh) * | 2015-03-20 | 2017-04-05 | 巨化集团技术中心 | 一种提高含氟聚合物粘结性的方法 |
| JP6680891B2 (ja) | 2016-01-21 | 2020-04-15 | スリーエム イノベイティブ プロパティズ カンパニー | フルオロエラストマーの積層プロセス |
| TW201908107A (zh) | 2017-07-19 | 2019-03-01 | 美商3M新設資產公司 | 氟聚合物的加成性加工 |
| TW201908426A (zh) | 2017-07-19 | 2019-03-01 | 美商3M新設資產公司 | 藉由加成性加工製造聚合物物品及聚合物複合物之方法以及聚合物及複合物品 |
| MX2020007901A (es) | 2018-01-26 | 2020-09-07 | Uwm Res Foundation Inc | Revestimiento compuesto hibrido en 3d. |
| US20220134254A1 (en) * | 2020-08-12 | 2022-05-05 | Resintech, Inc. | Processes and systems for removing per- and polyfluoroalkyl substances from fluids, such as potable water, using dimethylethanolamine resin |
| CN113527724B (zh) * | 2021-07-21 | 2023-12-08 | 常熟理工学院 | 一种粒径可控的含氟聚合物乳液凝聚方法 |
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| US2559752A (en) | 1951-03-06 | 1951-07-10 | Du Pont | Aqueous colloidal dispersions of polymers |
| US3037953A (en) | 1961-04-26 | 1962-06-05 | Du Pont | Concentration of aqueous colloidal dispersions of polytetrafluoroethylene |
| US3215741A (en) | 1963-01-08 | 1965-11-02 | Du Pont | Process for preparing maine oxides |
| US3283007A (en) | 1963-06-28 | 1966-11-01 | Du Pont | Production of amine oxides |
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| US3882153A (en) | 1969-09-12 | 1975-05-06 | Kureha Chemical Ind Co Ltd | Method for recovering fluorinated carboxylic acid |
| DE2903981A1 (de) | 1979-02-02 | 1980-08-07 | Hoechst Ag | Rueckgewinnung fluorierter emulgatorsaeuren aus basischen anionenaustauschern |
| DE2908001C2 (de) | 1979-03-01 | 1981-02-19 | Hoechst Ag, 6000 Frankfurt | Verfahren zur Herstellung konzentrierter Dispersionen von Fluorpolymeren |
| US4380618A (en) | 1981-08-21 | 1983-04-19 | E. I. Du Pont De Nemours And Company | Batch polymerization process |
| US4576869A (en) | 1984-06-18 | 1986-03-18 | E. I. Du Pont De Nemours And Company | Tetrafluoroethylene fine powder and preparation thereof |
| DE3545152A1 (de) | 1985-12-19 | 1987-06-25 | Hoechst Ag | Verfahren zur herestellung von fluessigen, hochkonzentrierten aminoxiden und diese enthaltende faserpraeparationsmittel |
| US5219186A (en) * | 1990-02-06 | 1993-06-15 | Sierracin Corporation | Tube union |
| DE4026097A1 (de) | 1990-08-17 | 1992-02-20 | Hoechst Ag | Waessrige dispersionen von fluorhaltigen polymeren |
| DE4124134A1 (de) | 1991-07-20 | 1993-01-21 | Hoechst Ag | Konzentrierte, waessrige dispersionen von tetrafluorethylen-polymeren, verfahren zu deren herstellung und deren verwendung |
| US5272186A (en) | 1992-05-01 | 1993-12-21 | E. I. Du Pont De Nemours And Company | Concentration of fluoropolymer dispersions using acrylic polymers of high acid content |
| JP3346090B2 (ja) | 1995-03-31 | 2002-11-18 | 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組成物及びその用途 |
| US5844029A (en) * | 1995-09-25 | 1998-12-01 | General Electric Company | Polymer compositions containing hydrocarbon amine oxide and hydrocarbon amine oxide stabilizer compositions |
| US5998521A (en) | 1996-11-04 | 1999-12-07 | 3M Innovative Properties Company | Aqueous fluoropolymer compositions and method of preparing the same |
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| JPH1149817A (ja) * | 1997-07-30 | 1999-02-23 | Asahi Glass Co Ltd | アルコキシカルボニル基含有含フッ素ポリマーの凝集方法 |
| KR20010021601A (ko) * | 1997-08-01 | 2001-03-15 | 이노우에 노리유끼 | 폴리테트라플루오로에틸렌 입상분말의 제법 |
| JP3721772B2 (ja) | 1998-03-06 | 2005-11-30 | ユニマテック株式会社 | 撥水撥油剤 |
| US6177533B1 (en) | 1998-11-13 | 2001-01-23 | E. I. Du Pont De Nemours And Company | Polytetrafluoroethylene resin |
| DE19857111A1 (de) | 1998-12-11 | 2000-06-15 | Dyneon Gmbh | Wäßrige Dispersionen von Fluorpolymeren |
| JP2000212549A (ja) | 1999-01-25 | 2000-08-02 | Asahi Glass Co Ltd | 撥水撥油剤組成物およびその製造方法 |
| CN1205682C (zh) | 2000-04-07 | 2005-06-08 | 大金工业株式会社 | 电极用添加剂 |
| DE10035930A1 (de) * | 2000-07-21 | 2002-01-31 | Clariant Gmbh | Feinemulsionen |
| US6703068B2 (en) * | 2001-12-19 | 2004-03-09 | 3M Innovative Properties Company | Amine oxide coating compositions |
| US6465041B1 (en) | 2001-12-19 | 2002-10-15 | 3M Innovative Properties Company | Method of making gas diffusion layers for electrochemical cells |
| US6956078B2 (en) | 2002-01-04 | 2005-10-18 | E.I. Du Pont De Nemours And Company | Concentrated fluoropolymer dispersions |
| US6838078B2 (en) * | 2002-01-16 | 2005-01-04 | 3M Innovative Properties Company | Film-forming compositions and methods |
| EP1645572A4 (en) * | 2003-07-03 | 2009-05-06 | Daikin Ind Ltd | METHOD FOR CLEANING MATERIAL TO TREATMENT AND METHOD FOR PRODUCING COAGULATED MATERIAL |
| FR2873125B1 (fr) * | 2004-07-16 | 2008-09-05 | Arkema Sa | Melange maitre a base de polymere fluore et son utilisation pour l'extrusion des polyolefines |
| KR20070092728A (ko) * | 2004-12-07 | 2007-09-13 | 다우 글로벌 테크놀로지스 인크. | 플루오로중합체 가공 보조제 및 촉매 중화제를 포함하는중합체 |
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|---|---|
| EP2094784B1 (en) | 2011-10-26 |
| EP2094784A1 (en) | 2009-09-02 |
| US20110207905A1 (en) | 2011-08-25 |
| US20080132623A1 (en) | 2008-06-05 |
| JP2010511777A (ja) | 2010-04-15 |
| ATE530603T1 (de) | 2011-11-15 |
| US7956112B2 (en) | 2011-06-07 |
| US7956120B2 (en) | 2011-06-07 |
| CN101541883A (zh) | 2009-09-23 |
| CN101541883B (zh) | 2013-09-25 |
| US8097673B2 (en) | 2012-01-17 |
| WO2008070079A1 (en) | 2008-06-12 |
| US20100113680A1 (en) | 2010-05-06 |
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