ZA200504411B - Emulsifier free aqueous emulsion polymerization toproduce copolymers of a fluorinated olefin and hy drocarbon olefin. - Google Patents
Emulsifier free aqueous emulsion polymerization toproduce copolymers of a fluorinated olefin and hy drocarbon olefin. Download PDFInfo
- Publication number
- ZA200504411B ZA200504411B ZA200504411A ZA200504411A ZA200504411B ZA 200504411 B ZA200504411 B ZA 200504411B ZA 200504411 A ZA200504411 A ZA 200504411A ZA 200504411 A ZA200504411 A ZA 200504411A ZA 200504411 B ZA200504411 B ZA 200504411B
- Authority
- ZA
- South Africa
- Prior art keywords
- fluorinated
- olefin
- process according
- polymerization
- copolymer
- Prior art date
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- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 title claims description 72
- 150000001336 alkenes Chemical class 0.000 title claims description 40
- 229920001577 copolymer Polymers 0.000 title claims description 35
- 238000007720 emulsion polymerization reaction Methods 0.000 title claims description 18
- 239000003995 emulsifying agent Substances 0.000 title claims description 11
- 229920002313 fluoropolymer Polymers 0.000 claims description 55
- 239000004811 fluoropolymer Substances 0.000 claims description 55
- 238000006116 polymerization reaction Methods 0.000 claims description 50
- -1 hydrocarbon olefin Chemical class 0.000 claims description 46
- 239000002245 particle Substances 0.000 claims description 40
- 229930195733 hydrocarbon Natural products 0.000 claims description 39
- 239000007788 liquid Substances 0.000 claims description 36
- 239000004215 Carbon black (E152) Substances 0.000 claims description 35
- 239000000178 monomer Substances 0.000 claims description 32
- 238000000034 method Methods 0.000 claims description 29
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 claims description 14
- 238000007334 copolymerization reaction Methods 0.000 claims description 13
- 238000011065 in-situ storage Methods 0.000 claims description 8
- 239000003999 initiator Substances 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 8
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 claims description 5
- JRKICGRDRMAZLK-UHFFFAOYSA-L peroxydisulfate Chemical compound [O-]S(=O)(=O)OOS([O-])(=O)=O JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 claims description 5
- BQCIDUSAKPWEOX-UHFFFAOYSA-N 1,1-Difluoroethene Chemical compound FC(F)=C BQCIDUSAKPWEOX-UHFFFAOYSA-N 0.000 claims description 4
- 239000000443 aerosol Substances 0.000 claims description 4
- 150000002978 peroxides Chemical class 0.000 claims description 4
- 238000002844 melting Methods 0.000 claims description 2
- 230000008018 melting Effects 0.000 claims description 2
- 230000000379 polymerizing effect Effects 0.000 claims description 2
- 239000004094 surface-active agent Substances 0.000 description 18
- 150000001875 compounds Chemical class 0.000 description 16
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 11
- 150000002430 hydrocarbons Chemical class 0.000 description 9
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 7
- 239000005977 Ethylene Substances 0.000 description 7
- 125000004432 carbon atom Chemical group C* 0.000 description 7
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 7
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 7
- 229910052794 bromium Inorganic materials 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 229910052736 halogen Inorganic materials 0.000 description 6
- 150000002367 halogens Chemical class 0.000 description 6
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 5
- 229910052801 chlorine Inorganic materials 0.000 description 5
- 229910052731 fluorine Inorganic materials 0.000 description 5
- 229910052740 iodine Inorganic materials 0.000 description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- 239000003638 chemical reducing agent Substances 0.000 description 4
- UUAGAQFQZIEFAH-UHFFFAOYSA-N chlorotrifluoroethylene Chemical group FC(F)=C(F)Cl UUAGAQFQZIEFAH-UHFFFAOYSA-N 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- 239000011737 fluorine Substances 0.000 description 4
- 125000001153 fluoro group Chemical group F* 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
- 230000000977 initiatory effect Effects 0.000 description 4
- 239000011630 iodine Substances 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 3
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium peroxydisulfate Substances [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 3
- VAZSKTXWXKYQJF-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)OOS([O-])=O VAZSKTXWXKYQJF-UHFFFAOYSA-N 0.000 description 3
- 229910001870 ammonium persulfate Inorganic materials 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 239000012986 chain transfer agent Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 3
- 150000002825 nitriles Chemical class 0.000 description 3
- 239000007800 oxidant agent Substances 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 3
- RRZIJNVZMJUGTK-UHFFFAOYSA-N 1,1,2-trifluoro-2-(1,2,2-trifluoroethenoxy)ethene Chemical class FC(F)=C(F)OC(F)=C(F)F RRZIJNVZMJUGTK-UHFFFAOYSA-N 0.000 description 2
- 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 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 description 2
- 229920006125 amorphous polymer Polymers 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000001723 curing Methods 0.000 description 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
- 150000001983 dialkylethers Chemical class 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- ZQBFAOFFOQMSGJ-UHFFFAOYSA-N hexafluorobenzene Chemical compound FC1=C(F)C(F)=C(F)C(F)=C1F ZQBFAOFFOQMSGJ-UHFFFAOYSA-N 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 239000011572 manganese Substances 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 125000002560 nitrile group Chemical group 0.000 description 2
- FYJQJMIEZVMYSD-UHFFFAOYSA-N perfluoro-2-butyltetrahydrofuran Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C1(F)OC(F)(F)C(F)(F)C1(F)F FYJQJMIEZVMYSD-UHFFFAOYSA-N 0.000 description 2
- RVZRBWKZFJCCIB-UHFFFAOYSA-N perfluorotributylamine Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)N(C(F)(F)C(F)(F)C(F)(F)C(F)(F)F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F RVZRBWKZFJCCIB-UHFFFAOYSA-N 0.000 description 2
- AQZYBQIAUSKCCS-UHFFFAOYSA-N perfluorotripentylamine Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)N(C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F AQZYBQIAUSKCCS-UHFFFAOYSA-N 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
- 239000011593 sulfur Chemical group 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 238000010557 suspension polymerization reaction Methods 0.000 description 2
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 2
- 125000005270 trialkylamine group Chemical group 0.000 description 2
- AXFFGMPNSZVEDX-UHFFFAOYSA-N 1,1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,12,12,13,13,14,14,15,15,16,16,17,17,18,18,19,19,20,20,21,21,22,22,23,23,24,24,24-pentacontafluorotetracosane 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)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)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F AXFFGMPNSZVEDX-UHFFFAOYSA-N 0.000 description 1
- OKIYQFLILPKULA-UHFFFAOYSA-N 1,1,1,2,2,3,3,4,4-nonafluoro-4-methoxybutane Chemical compound COC(F)(F)C(F)(F)C(F)(F)C(F)(F)F OKIYQFLILPKULA-UHFFFAOYSA-N 0.000 description 1
- LWRNQOBXRHWPGE-UHFFFAOYSA-N 1,1,2,2,3,3,4,4,4a,5,5,6,6,7,7,8,8a-heptadecafluoro-8-(trifluoromethyl)naphthalene Chemical compound FC1(F)C(F)(F)C(F)(F)C(F)(F)C2(F)C(C(F)(F)F)(F)C(F)(F)C(F)(F)C(F)(F)C21F LWRNQOBXRHWPGE-UHFFFAOYSA-N 0.000 description 1
- NZXAVWBNLOQPGY-UHFFFAOYSA-N 1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8-hexadecafluoro-4a,8a-bis(trifluoromethyl)naphthalene Chemical compound FC(F)(F)C12C(F)(F)C(F)(F)C(F)(F)C(F)(F)C1(C(F)(F)F)C(F)(F)C(F)(F)C(F)(F)C2(F)F NZXAVWBNLOQPGY-UHFFFAOYSA-N 0.000 description 1
- QIROQPWSJUXOJC-UHFFFAOYSA-N 1,1,2,2,3,3,4,4,5,5,6-undecafluoro-6-(trifluoromethyl)cyclohexane Chemical compound FC(F)(F)C1(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C1(F)F QIROQPWSJUXOJC-UHFFFAOYSA-N 0.000 description 1
- BZPCMSSQHRAJCC-UHFFFAOYSA-N 1,2,3,3,4,4,5,5,5-nonafluoro-1-(1,2,3,3,4,4,5,5,5-nonafluoropent-1-enoxy)pent-1-ene Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)=C(F)OC(F)=C(F)C(F)(F)C(F)(F)C(F)(F)F BZPCMSSQHRAJCC-UHFFFAOYSA-N 0.000 description 1
- OMNCMLIVRODHHP-UHFFFAOYSA-N 1,2,3,3,4,4,5,5-octafluoro-1-[1,2,3,3,4,4,5,5-octafluoro-5-(trifluoromethoxy)pent-1-enoxy]-5-(trifluoromethoxy)pent-1-ene Chemical compound FC(OC(F)=C(F)C(F)(F)C(F)(F)C(F)(F)OC(F)(F)F)=C(F)C(F)(F)C(F)(F)C(F)(F)OC(F)(F)F OMNCMLIVRODHHP-UHFFFAOYSA-N 0.000 description 1
- JDCMOHAFGDQQJX-UHFFFAOYSA-N 1,2,3,4,5,6,7,8-octafluoronaphthalene Chemical compound FC1=C(F)C(F)=C(F)C2=C(F)C(F)=C(F)C(F)=C21 JDCMOHAFGDQQJX-UHFFFAOYSA-N 0.000 description 1
- USPWUOFNOTUBAD-UHFFFAOYSA-N 1,2,3,4,5-pentafluoro-6-(trifluoromethyl)benzene Chemical compound FC1=C(F)C(F)=C(C(F)(F)F)C(F)=C1F USPWUOFNOTUBAD-UHFFFAOYSA-N 0.000 description 1
- AYCANDRGVPTASA-UHFFFAOYSA-N 1-bromo-1,2,2-trifluoroethene Chemical group FC(F)=C(F)Br AYCANDRGVPTASA-UHFFFAOYSA-N 0.000 description 1
- DFUYAWQUODQGFF-UHFFFAOYSA-N 1-ethoxy-1,1,2,2,3,3,4,4,4-nonafluorobutane Chemical compound CCOC(F)(F)C(F)(F)C(F)(F)C(F)(F)F DFUYAWQUODQGFF-UHFFFAOYSA-N 0.000 description 1
- LYIPDZSLYLDLCU-UHFFFAOYSA-N 2,2,3,3-tetrafluoro-3-[1,1,1,2,3,3-hexafluoro-3-(1,2,2-trifluoroethenoxy)propan-2-yl]oxypropanenitrile Chemical compound FC(F)=C(F)OC(F)(F)C(F)(C(F)(F)F)OC(F)(F)C(F)(F)C#N LYIPDZSLYLDLCU-UHFFFAOYSA-N 0.000 description 1
- LCPVQAHEFVXVKT-UHFFFAOYSA-N 2-(2,4-difluorophenoxy)pyridin-3-amine Chemical compound NC1=CC=CN=C1OC1=CC=C(F)C=C1F LCPVQAHEFVXVKT-UHFFFAOYSA-N 0.000 description 1
- QZGNGBWAMYFUST-UHFFFAOYSA-N 2-bromo-1,1-difluoroethene Chemical group FC(F)=CBr QZGNGBWAMYFUST-UHFFFAOYSA-N 0.000 description 1
- GVCWGFZDSIWLMO-UHFFFAOYSA-N 4-bromo-3,3,4,4-tetrafluorobut-1-ene Chemical compound FC(F)(Br)C(F)(F)C=C GVCWGFZDSIWLMO-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- SXWUSKUNDTYYNV-UHFFFAOYSA-N FC(=C(C(C(C(F)(F)F)(OC(C(C(F)(F)F)(F)F)(F)F)F)(F)F)F)OC(=C(F)C(C(C(F)(F)F)(F)OC(C(C(F)(F)F)(F)F)(F)F)(F)F)F Chemical compound FC(=C(C(C(C(F)(F)F)(OC(C(C(F)(F)F)(F)F)(F)F)F)(F)F)F)OC(=C(F)C(C(C(F)(F)F)(F)OC(C(C(F)(F)F)(F)F)(F)F)(F)F)F SXWUSKUNDTYYNV-UHFFFAOYSA-N 0.000 description 1
- GHSBRBCKXUSPAS-UHFFFAOYSA-N FC(=C(C(C(OC(F)(F)F)(F)F)(F)F)F)OC(=C(F)C(C(F)(F)OC(F)(F)F)(F)F)F Chemical compound FC(=C(C(C(OC(F)(F)F)(F)F)(F)F)F)OC(=C(F)C(C(F)(F)OC(F)(F)F)(F)F)F GHSBRBCKXUSPAS-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 1
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000007824 aliphatic compounds Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 239000003957 anion exchange resin Substances 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 125000004429 atom Chemical group 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
- 150000001555 benzenes Chemical class 0.000 description 1
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- 125000001246 bromo group Chemical group Br* 0.000 description 1
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- 150000001721 carbon Chemical group 0.000 description 1
- 150000001734 carboxylic acid salts Chemical class 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 125000004966 cyanoalkyl group Chemical group 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
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- 238000002296 dynamic light scattering Methods 0.000 description 1
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- 230000007613 environmental effect Effects 0.000 description 1
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- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical group FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
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- 125000002346 iodo group Chemical group I* 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- RGVLTEMOWXGQOS-UHFFFAOYSA-L manganese(2+);oxalate Chemical compound [Mn+2].[O-]C(=O)C([O-])=O RGVLTEMOWXGQOS-UHFFFAOYSA-L 0.000 description 1
- AHSBSUVHXDIAEY-UHFFFAOYSA-K manganese(iii) acetate Chemical compound [Mn+3].CC([O-])=O.CC([O-])=O.CC([O-])=O AHSBSUVHXDIAEY-UHFFFAOYSA-K 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
- QLOAVXSYZAJECW-UHFFFAOYSA-N methane;molecular fluorine Chemical compound C.FF QLOAVXSYZAJECW-UHFFFAOYSA-N 0.000 description 1
- 239000004530 micro-emulsion Substances 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Chemical group 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 150000002976 peresters Chemical class 0.000 description 1
- 229950011087 perflunafene Drugs 0.000 description 1
- 125000006551 perfluoro alkylene group Chemical group 0.000 description 1
- LOQGSOTUHASIHI-UHFFFAOYSA-N perfluoro-1,3-dimethylcyclohexane Chemical compound FC(F)(F)C1(F)C(F)(F)C(F)(F)C(F)(F)C(F)(C(F)(F)F)C1(F)F LOQGSOTUHASIHI-UHFFFAOYSA-N 0.000 description 1
- UWEYRJFJVCLAGH-IJWZVTFUSA-N perfluorodecalin Chemical compound FC1(F)C(F)(F)C(F)(F)C(F)(F)[C@@]2(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)[C@@]21F UWEYRJFJVCLAGH-IJWZVTFUSA-N 0.000 description 1
- QKENRHXGDUPTEM-UHFFFAOYSA-N perfluorophenanthrene Chemical compound FC1(F)C(F)(F)C(F)(F)C(F)(F)C2(F)C3(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C3(F)C(F)(F)C(F)(F)C21F QKENRHXGDUPTEM-UHFFFAOYSA-N 0.000 description 1
- JAJLKEVKNDUJBG-UHFFFAOYSA-N perfluorotripropylamine Chemical compound FC(F)(F)C(F)(F)C(F)(F)N(C(F)(F)C(F)(F)C(F)(F)F)C(F)(F)C(F)(F)C(F)(F)F JAJLKEVKNDUJBG-UHFFFAOYSA-N 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229920002493 poly(chlorotrifluoroethylene) Polymers 0.000 description 1
- DJEHXEMURTVAOE-UHFFFAOYSA-M potassium bisulfite Chemical compound [K+].OS([O-])=O DJEHXEMURTVAOE-UHFFFAOYSA-M 0.000 description 1
- 229940099427 potassium bisulfite Drugs 0.000 description 1
- 235000010259 potassium hydrogen sulphite Nutrition 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
- 239000001294 propane Substances 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000006479 redox reaction Methods 0.000 description 1
- XWGJFPHUCFXLBL-UHFFFAOYSA-M rongalite Chemical compound [Na+].OCS([O-])=O XWGJFPHUCFXLBL-UHFFFAOYSA-M 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- CHQMHPLRPQMAMX-UHFFFAOYSA-L sodium persulfate Substances [Na+].[Na+].[O-]S(=O)(=O)OOS([O-])(=O)=O CHQMHPLRPQMAMX-UHFFFAOYSA-L 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical class [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- 150000004764 thiosulfuric acid derivatives Chemical class 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 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
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Polymerisation Methods In General (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US42277002P | 2002-10-31 | 2002-10-31 |
Publications (1)
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|---|---|
| ZA200504411B true ZA200504411B (en) | 2006-02-22 |
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| Country | Link |
|---|---|
| US (1) | US7064170B2 (enExample) |
| EP (1) | EP1556426B1 (enExample) |
| JP (1) | JP2006504844A (enExample) |
| CN (1) | CN100354324C (enExample) |
| AT (1) | ATE430169T1 (enExample) |
| AU (1) | AU2003291646A1 (enExample) |
| DE (1) | DE60327452D1 (enExample) |
| RU (1) | RU2342403C2 (enExample) |
| WO (1) | WO2004041878A1 (enExample) |
| ZA (1) | ZA200504411B (enExample) |
Families Citing this family (47)
| Publication number | Priority date | Publication date | Assignee | Title |
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| US7125941B2 (en) * | 2001-03-26 | 2006-10-24 | 3M Innovative Properties Company | Aqueous emulsion polymerization process for producing fluoropolymers |
| JP4624646B2 (ja) * | 2001-05-02 | 2011-02-02 | スリーエム イノベイティブ プロパティズ カンパニー | フルオロポリマーを製造するための連鎖移動剤としてのエーテルの存在下での水性乳化重合 |
| US7279522B2 (en) | 2001-09-05 | 2007-10-09 | 3M Innovative Properties Company | Fluoropolymer dispersions containing no or little low molecular weight fluorinated surfactant |
| JP2006504844A (ja) * | 2002-10-31 | 2006-02-09 | スリーエム イノベイティブ プロパティズ カンパニー | フッ化オレフィンと炭化水素オレフィンとのコポリマーを製造するための、乳化剤非含有水性乳化重合 |
| ATE502062T1 (de) | 2003-10-24 | 2011-04-15 | 3M Innovative Properties Co | Wässrige dispersionen von polytetrafluorethylenteilchen |
| EP1533325B1 (en) | 2003-11-17 | 2011-10-19 | 3M Innovative Properties Company | Aqueous dispersions of polytetrafluoroethylene having a low amount of fluorinated surfactant |
| PL1570917T3 (pl) * | 2004-03-01 | 2009-10-30 | 3M Innovative Properties Co | Sposób powlekania substratu dyspersją fluoropolimeru |
| US7691932B2 (en) | 2004-09-27 | 2010-04-06 | 3M Innovative Properties Company | Method of making a composition and nanocomposites therefrom |
| US20060270780A1 (en) * | 2005-05-25 | 2006-11-30 | Ping Xu | High purity perfluoroelastomer composites and a processes to produce the same |
| US7488781B2 (en) * | 2005-05-25 | 2009-02-10 | Gore Enterprise Holdings, Inc. | High purity transparent perfluoroelastomer parts and a process to produce the same |
| GB2427170A (en) * | 2005-06-17 | 2006-12-20 | 3M Innovative Properties Co | Fluoropolymer film having glass microspheres |
| GB0525978D0 (en) * | 2005-12-21 | 2006-02-01 | 3M Innovative Properties Co | Fluorinated Surfactants For Making Fluoropolymers |
| US20070015937A1 (en) * | 2005-07-15 | 2007-01-18 | 3M Innovative Properties Company | Process for recovery of fluorinated carboxylic acid surfactants from exhaust gas |
| GB0514387D0 (en) * | 2005-07-15 | 2005-08-17 | 3M Innovative Properties Co | Aqueous emulsion polymerization of fluorinated monomers using a perfluoropolyether surfactant |
| GB0523853D0 (en) | 2005-11-24 | 2006-01-04 | 3M Innovative Properties Co | Fluorinated surfactants for use in making a fluoropolymer |
| GB0514398D0 (en) * | 2005-07-15 | 2005-08-17 | 3M Innovative Properties Co | Aqueous emulsion polymerization of fluorinated monomers using a fluorinated surfactant |
| US20080015304A1 (en) | 2006-07-13 | 2008-01-17 | Klaus Hintzer | Aqueous emulsion polymerization process for producing fluoropolymers |
| GB2430437A (en) * | 2005-09-27 | 2007-03-28 | 3M Innovative Properties Co | Method of making a fluoropolymer |
| US7728087B2 (en) | 2005-12-23 | 2010-06-01 | 3M Innovative Properties Company | Fluoropolymer dispersion and method for making the same |
| EP2017292B1 (en) | 2006-05-10 | 2011-09-07 | Daikin Industries, Ltd. | Process for production of fluorine-containing polymers |
| US7754795B2 (en) * | 2006-05-25 | 2010-07-13 | 3M Innovative Properties Company | Coating composition |
| US20070276103A1 (en) * | 2006-05-25 | 2007-11-29 | 3M Innovative Properties Company | Fluorinated Surfactants |
| US8119750B2 (en) * | 2006-07-13 | 2012-02-21 | 3M Innovative Properties Company | Explosion taming surfactants for the production of perfluoropolymers |
| BRPI0807109A2 (pt) * | 2007-02-16 | 2014-05-06 | 3M Innovative Properties Co | Sistema e processo para a remoção de fluoroquiímicos da água |
| 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 |
| KR20100017848A (ko) * | 2007-05-23 | 2010-02-16 | 쓰리엠 이노베이티브 프로퍼티즈 컴파니 | 플루오르화 계면활성제의 수성 조성물 및 그의 사용 방법 |
| CN101679569A (zh) * | 2007-06-06 | 2010-03-24 | 3M创新有限公司 | 氟化醚组合物以及使用该组合物的方法 |
| JP5532532B2 (ja) * | 2007-06-25 | 2014-06-25 | ダイキン工業株式会社 | 低分子量ポリテトラフルオロエチレン水性分散液及びその製造方法 |
| GB0712191D0 (en) * | 2007-06-25 | 2007-08-01 | 3M Innovative Properties Co | Process for removing fluorinated compounds for an aqueous phase originating from the preparation of fluoropolymers |
| US9650479B2 (en) | 2007-10-04 | 2017-05-16 | W. L. Gore & Associates, Inc. | Dense articles formed from tetrafluoroethylene core shell copolymers and methods of making the same |
| US9040646B2 (en) | 2007-10-04 | 2015-05-26 | W. L. Gore & Associates, Inc. | Expandable TFE copolymers, methods of making, and porous, expanded articles thereof |
| US8637144B2 (en) * | 2007-10-04 | 2014-01-28 | W. L. Gore & Associates, Inc. | Expandable TFE copolymers, method of making, and porous, expended articles thereof |
| WO2010009191A2 (en) * | 2008-07-18 | 2010-01-21 | 3M Innovative Properties Company | Fluorinated ether compounds and methods of using the same |
| US20110232530A1 (en) * | 2008-11-25 | 2011-09-29 | Dams Rudolf J | Fluorinated ether urethanes and methods of using the same |
| US8629089B2 (en) | 2008-12-18 | 2014-01-14 | 3M Innovative Properties Company | Method of contacting hydrocarbon-bearing formations with fluorinated ether compositions |
| JP5407643B2 (ja) * | 2009-07-31 | 2014-02-05 | 旭硝子株式会社 | 含フッ素共重合体の製造方法 |
| WO2012064846A1 (en) | 2010-11-09 | 2012-05-18 | E. I. Du Pont De Nemours And Company | Nucleation in aqueous polymerization of fluoromonomer |
| JP6030562B2 (ja) | 2010-11-09 | 2016-11-24 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニーＥ．Ｉ．Ｄｕ Ｐｏｎｔ Ｄｅ Ｎｅｍｏｕｒｓ Ａｎｄ Ｃｏｍｐａｎｙ | 水性分散体フルオロモノマーの重合における炭化水素含有界面活性剤のテロゲン性挙動の低下 |
| CN103201300B (zh) | 2010-11-09 | 2016-11-09 | 纳幕尔杜邦公司 | 使用烃表面活性剂的含氟单体的含水聚合 |
| WO2012150253A1 (en) * | 2011-05-03 | 2012-11-08 | Solvay Specialty Polymers Italy S.P.A. | Method for manufacturing fluoroelastomers |
| CA2839389C (en) | 2011-07-15 | 2020-09-01 | Solvay Specialty Polymers Italy S.P.A. | Aqueous vinylidene fluoride polymer latex |
| WO2014115679A1 (ja) * | 2013-01-23 | 2014-07-31 | ダイキン工業株式会社 | 含フッ素エーテルの回収方法 |
| EP3074430B1 (en) | 2013-11-26 | 2019-02-20 | The Chemours Company FC, LLC | Employing polyalkylene oxides for nucleation in aqueous polymerization of fluoromonomer |
| US9644054B2 (en) | 2014-12-19 | 2017-05-09 | W. L. Gore & Associates, Inc. | Dense articles formed from tetrafluoroethylene core shell copolymers and methods of making the same |
| CN110494516B (zh) * | 2017-04-11 | 2022-11-04 | 索尔维特殊聚合物意大利有限公司 | 用于制造氟聚合物的方法 |
| CN110078855B (zh) * | 2019-04-22 | 2020-07-14 | 中昊晨光化工研究院有限公司 | 一种含氟聚合物及其制备方法 |
| CN116178598A (zh) * | 2022-06-20 | 2023-05-30 | 福建海德福新材料有限公司 | 一种四氟乙烯基聚合物树脂及其制备方法 |
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| JP2006504844A (ja) * | 2002-10-31 | 2006-02-09 | スリーエム イノベイティブ プロパティズ カンパニー | フッ化オレフィンと炭化水素オレフィンとのコポリマーを製造するための、乳化剤非含有水性乳化重合 |
-
2003
- 2003-10-21 JP JP2004550055A patent/JP2006504844A/ja active Pending
- 2003-10-21 CN CNB2003801022455A patent/CN100354324C/zh not_active Expired - Fee Related
- 2003-10-21 AU AU2003291646A patent/AU2003291646A1/en not_active Abandoned
- 2003-10-21 US US10/690,088 patent/US7064170B2/en not_active Expired - Fee Related
- 2003-10-21 WO PCT/US2003/033233 patent/WO2004041878A1/en not_active Ceased
- 2003-10-21 RU RU2005111865/04A patent/RU2342403C2/ru not_active IP Right Cessation
- 2003-10-21 DE DE60327452T patent/DE60327452D1/de not_active Expired - Fee Related
- 2003-10-21 EP EP03768534A patent/EP1556426B1/en not_active Expired - Lifetime
- 2003-10-21 AT AT03768534T patent/ATE430169T1/de not_active IP Right Cessation
-
2005
- 2005-05-30 ZA ZA200504411A patent/ZA200504411B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CN1708519A (zh) | 2005-12-14 |
| RU2005111865A (ru) | 2005-10-27 |
| US7064170B2 (en) | 2006-06-20 |
| DE60327452D1 (de) | 2009-06-10 |
| ATE430169T1 (de) | 2009-05-15 |
| CN100354324C (zh) | 2007-12-12 |
| AU2003291646A1 (en) | 2004-06-07 |
| US20040087703A1 (en) | 2004-05-06 |
| JP2006504844A (ja) | 2006-02-09 |
| RU2342403C2 (ru) | 2008-12-27 |
| WO2004041878A1 (en) | 2004-05-21 |
| EP1556426A1 (en) | 2005-07-27 |
| EP1556426B1 (en) | 2009-04-29 |
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