JP2005534750A - フルオロエラストマーの製造方法 - Google Patents
フルオロエラストマーの製造方法 Download PDFInfo
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- JP2005534750A JP2005534750A JP2004524923A JP2004524923A JP2005534750A JP 2005534750 A JP2005534750 A JP 2005534750A JP 2004524923 A JP2004524923 A JP 2004524923A JP 2004524923 A JP2004524923 A JP 2004524923A JP 2005534750 A JP2005534750 A JP 2005534750A
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- Prior art keywords
- fluoropolymer
- fluorinated
- liquid
- group
- cured
- Prior art date
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- 229920001973 fluoroelastomer Polymers 0.000 title claims description 51
- 238000004519 manufacturing process Methods 0.000 title claims description 15
- 239000000178 monomer Substances 0.000 claims abstract description 72
- 239000007788 liquid Substances 0.000 claims abstract description 63
- 239000004530 micro-emulsion Substances 0.000 claims abstract description 62
- 150000002430 hydrocarbons Chemical class 0.000 claims abstract description 25
- 150000003839 salts Chemical class 0.000 claims abstract description 25
- 239000002253 acid Substances 0.000 claims abstract description 23
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 19
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims abstract description 8
- 238000002156 mixing Methods 0.000 claims abstract description 6
- 229920002313 fluoropolymer Polymers 0.000 claims description 81
- 239000004811 fluoropolymer Substances 0.000 claims description 81
- 239000000203 mixture Substances 0.000 claims description 58
- 150000001875 compounds Chemical class 0.000 claims description 47
- 238000006116 polymerization reaction Methods 0.000 claims description 30
- 238000000034 method Methods 0.000 claims description 26
- 125000004432 carbon atom Chemical group C* 0.000 claims description 23
- 239000003999 initiator Substances 0.000 claims description 19
- 239000000460 chlorine Substances 0.000 claims description 17
- 229910052731 fluorine Inorganic materials 0.000 claims description 17
- 229910052801 chlorine Inorganic materials 0.000 claims description 16
- 238000007720 emulsion polymerization reaction Methods 0.000 claims description 16
- 150000001768 cations Chemical class 0.000 claims description 14
- 229910052794 bromium Inorganic materials 0.000 claims description 13
- 229910052740 iodine Inorganic materials 0.000 claims description 10
- 125000002560 nitrile group Chemical group 0.000 claims description 9
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 8
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 8
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 7
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 claims description 7
- 150000001336 alkenes Chemical class 0.000 claims description 7
- 229920005548 perfluoropolymer Polymers 0.000 claims description 7
- 150000003841 chloride salts Chemical class 0.000 claims description 6
- ZQBFAOFFOQMSGJ-UHFFFAOYSA-N hexafluorobenzene Chemical compound FC1=C(F)C(F)=C(F)C(F)=C1F ZQBFAOFFOQMSGJ-UHFFFAOYSA-N 0.000 claims description 6
- 239000011630 iodine Substances 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 150000003254 radicals Chemical class 0.000 claims description 5
- DOUHZFSGSXMPIE-UHFFFAOYSA-N hydroxidooxidosulfur(.) Chemical compound [O]SO DOUHZFSGSXMPIE-UHFFFAOYSA-N 0.000 claims description 4
- 238000002835 absorbance Methods 0.000 claims description 3
- 239000007800 oxidant agent Substances 0.000 claims description 3
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 3
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 2
- 230000001590 oxidative effect Effects 0.000 claims description 2
- UJMWVICAENGCRF-UHFFFAOYSA-N oxygen difluoride Chemical group FOF UJMWVICAENGCRF-UHFFFAOYSA-N 0.000 claims description 2
- 125000006551 perfluoro alkylene group Chemical group 0.000 claims description 2
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 claims 1
- 238000000944 Soxhlet extraction Methods 0.000 claims 1
- 239000006185 dispersion Substances 0.000 claims 1
- 238000003682 fluorination reaction Methods 0.000 claims 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims 1
- 238000001228 spectrum Methods 0.000 claims 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 abstract description 6
- 150000001335 aliphatic alkanes Chemical class 0.000 abstract 1
- -1 alkane sulfonic acids Chemical class 0.000 description 34
- 238000001723 curing Methods 0.000 description 31
- 150000002978 peroxides Chemical class 0.000 description 18
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 18
- 239000004094 surface-active agent Substances 0.000 description 17
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 16
- 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 15
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 15
- 229910052757 nitrogen Inorganic materials 0.000 description 15
- 150000002825 nitriles Chemical class 0.000 description 13
- 125000003118 aryl group Chemical group 0.000 description 12
- 125000000217 alkyl group Chemical group 0.000 description 11
- 239000011737 fluorine Substances 0.000 description 11
- 150000002500 ions Chemical class 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- 229910052736 halogen Inorganic materials 0.000 description 10
- 150000002367 halogens Chemical class 0.000 description 10
- 239000003795 chemical substances by application Substances 0.000 description 9
- 239000000839 emulsion Substances 0.000 description 9
- RRZIJNVZMJUGTK-UHFFFAOYSA-N 1,1,2-trifluoro-2-(1,2,2-trifluoroethenoxy)ethene Chemical compound FC(F)=C(F)OC(F)=C(F)F RRZIJNVZMJUGTK-UHFFFAOYSA-N 0.000 description 8
- BQCIDUSAKPWEOX-UHFFFAOYSA-N 1,1-Difluoroethene Chemical compound FC(F)=C BQCIDUSAKPWEOX-UHFFFAOYSA-N 0.000 description 8
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 8
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 8
- 150000001450 anions Chemical class 0.000 description 8
- 125000001153 fluoro group Chemical group F* 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
- 229910052739 hydrogen Inorganic materials 0.000 description 8
- 229920000642 polymer Polymers 0.000 description 8
- 239000011734 sodium Substances 0.000 description 8
- 125000003342 alkenyl group Chemical group 0.000 description 7
- 229910021529 ammonia Inorganic materials 0.000 description 7
- 229910052760 oxygen Inorganic materials 0.000 description 7
- 239000002243 precursor Substances 0.000 description 7
- 229920001971 elastomer Polymers 0.000 description 6
- 229930195733 hydrocarbon Natural products 0.000 description 6
- 229910052698 phosphorus Inorganic materials 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 229910052708 sodium Inorganic materials 0.000 description 6
- 229910052717 sulfur Inorganic materials 0.000 description 6
- 229910052783 alkali metal Inorganic materials 0.000 description 5
- 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 5
- 239000003054 catalyst Substances 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 238000004898 kneading Methods 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 4
- 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 4
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical group [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 4
- 229910001870 ammonium persulfate Inorganic materials 0.000 description 4
- 125000003710 aryl alkyl group Chemical group 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
- CEIPQQODRKXDSB-UHFFFAOYSA-N ethyl 3-(6-hydroxynaphthalen-2-yl)-1H-indazole-5-carboximidate dihydrochloride Chemical compound Cl.Cl.C1=C(O)C=CC2=CC(C3=NNC4=CC=C(C=C43)C(=N)OCC)=CC=C21 CEIPQQODRKXDSB-UHFFFAOYSA-N 0.000 description 4
- 239000000446 fuel Substances 0.000 description 4
- 125000005842 heteroatom Chemical group 0.000 description 4
- 150000007522 mineralic acids Chemical class 0.000 description 4
- 150000004010 onium ions Chemical class 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 239000002245 particle Substances 0.000 description 4
- 239000011574 phosphorus Substances 0.000 description 4
- 229910052700 potassium Inorganic materials 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 239000011593 sulfur Substances 0.000 description 4
- VQFBJCOENMVGJC-UHFFFAOYSA-L 2,2,3,3,4,4,5,5-octafluorohexanedioate;tetrabutylphosphanium Chemical compound CCCC[P+](CCCC)(CCCC)CCCC.CCCC[P+](CCCC)(CCCC)CCCC.[O-]C(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C([O-])=O VQFBJCOENMVGJC-UHFFFAOYSA-L 0.000 description 3
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- 239000002879 Lewis base Substances 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
- 150000007513 acids Chemical class 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 150000001340 alkali metals Chemical group 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 150000001721 carbon Chemical group 0.000 description 3
- 150000001735 carboxylic acids Chemical class 0.000 description 3
- UUAGAQFQZIEFAH-UHFFFAOYSA-N chlorotrifluoroethylene Chemical group FC(F)=C(F)Cl UUAGAQFQZIEFAH-UHFFFAOYSA-N 0.000 description 3
- 238000007334 copolymerization reaction Methods 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- 125000004093 cyano group Chemical group *C#N 0.000 description 3
- 125000000392 cycloalkenyl group Chemical group 0.000 description 3
- 125000000753 cycloalkyl group Chemical group 0.000 description 3
- 239000000806 elastomer Substances 0.000 description 3
- 238000010556 emulsion polymerization method Methods 0.000 description 3
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 3
- 150000007527 lewis bases Chemical class 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000002609 medium Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 150000007524 organic acids Chemical class 0.000 description 3
- 150000001451 organic peroxides Chemical class 0.000 description 3
- 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 3
- 125000005385 peroxodisulfate group Chemical group 0.000 description 3
- 150000004965 peroxy acids Chemical class 0.000 description 3
- 238000012545 processing Methods 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 239000000523 sample Substances 0.000 description 3
- TXEIIPDJKFWEEC-UHFFFAOYSA-N tafamidis Chemical compound O1C2=CC(C(=O)O)=CC=C2N=C1C1=CC(Cl)=CC(Cl)=C1 TXEIIPDJKFWEEC-UHFFFAOYSA-N 0.000 description 3
- 125000005270 trialkylamine group Chemical group 0.000 description 3
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 description 2
- TWIYDBQRYCWOAU-UHFFFAOYSA-N 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfinic acid Chemical compound OS(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F TWIYDBQRYCWOAU-UHFFFAOYSA-N 0.000 description 2
- KOMNUTZXSVSERR-UHFFFAOYSA-N 1,3,5-tris(prop-2-enyl)-1,3,5-triazinane-2,4,6-trione Chemical compound C=CCN1C(=O)N(CC=C)C(=O)N(CC=C)C1=O KOMNUTZXSVSERR-UHFFFAOYSA-N 0.000 description 2
- SGUVLZREKBPKCE-UHFFFAOYSA-N 1,5-diazabicyclo[4.3.0]-non-5-ene Chemical compound C1CCN=C2CCCN21 SGUVLZREKBPKCE-UHFFFAOYSA-N 0.000 description 2
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 2
- 229930185605 Bisphenol Natural products 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
- 229920006169 Perfluoroelastomer Polymers 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical class OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 150000001342 alkaline earth metals Chemical group 0.000 description 2
- 150000004703 alkoxides Chemical class 0.000 description 2
- 125000002877 alkyl aryl group Chemical group 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- XQJHRCVXRAJIDY-UHFFFAOYSA-N aminophosphine Chemical compound PN XQJHRCVXRAJIDY-UHFFFAOYSA-N 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 229910052787 antimony Inorganic materials 0.000 description 2
- 229910052785 arsenic Inorganic materials 0.000 description 2
- 235000019400 benzoyl peroxide Nutrition 0.000 description 2
- 150000001649 bromium compounds Chemical class 0.000 description 2
- 125000001246 bromo group Chemical group Br* 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000006229 carbon black Substances 0.000 description 2
- 150000001805 chlorine compounds Chemical class 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 2
- ZQMIGQNCOMNODD-UHFFFAOYSA-N diacetyl peroxide Chemical compound CC(=O)OOC(C)=O ZQMIGQNCOMNODD-UHFFFAOYSA-N 0.000 description 2
- 230000001804 emulsifying effect Effects 0.000 description 2
- 125000003709 fluoroalkyl group Chemical group 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 150000004679 hydroxides Chemical class 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- 230000000977 initiatory effect Effects 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- CVMIVKAWUQZOBP-UHFFFAOYSA-L manganic acid Chemical class O[Mn](O)(=O)=O CVMIVKAWUQZOBP-UHFFFAOYSA-L 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000011368 organic material Substances 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 2
- 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 2
- JRKICGRDRMAZLK-UHFFFAOYSA-L persulfate group Chemical group S(=O)(=O)([O-])OOS(=O)(=O)[O-] JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 2
- 150000004714 phosphonium salts Chemical class 0.000 description 2
- 238000011417 postcuring Methods 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 2
- 238000000518 rheometry Methods 0.000 description 2
- 239000004065 semiconductor Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 125000005497 tetraalkylphosphonium group Chemical group 0.000 description 2
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 2
- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 description 2
- VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 description 2
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- BXYHVFRRNNWPMB-UHFFFAOYSA-N tetramethylphosphanium Chemical compound C[P+](C)(C)C BXYHVFRRNNWPMB-UHFFFAOYSA-N 0.000 description 1
- GJSGYPDDPQRWPK-UHFFFAOYSA-N tetrapentylammonium Chemical compound CCCCC[N+](CCCCC)(CCCCC)CCCCC GJSGYPDDPQRWPK-UHFFFAOYSA-N 0.000 description 1
- IUVXCVGGLRYGFE-UHFFFAOYSA-N tetraphenyl-lambda5-arsane hydrochloride Chemical compound C1=CC=C(C=C1)[AsH](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC=C4.Cl IUVXCVGGLRYGFE-UHFFFAOYSA-N 0.000 description 1
- USFPINLPPFWTJW-UHFFFAOYSA-N tetraphenylphosphonium Chemical compound C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 USFPINLPPFWTJW-UHFFFAOYSA-N 0.000 description 1
- OSBSFAARYOCBHB-UHFFFAOYSA-N tetrapropylammonium Chemical compound CCC[N+](CCC)(CCC)CCC OSBSFAARYOCBHB-UHFFFAOYSA-N 0.000 description 1
- 125000004149 thio group Chemical group *S* 0.000 description 1
- DHCDFWKWKRSZHF-UHFFFAOYSA-L thiosulfate(2-) Chemical compound [O-]S([S-])(=O)=O DHCDFWKWKRSZHF-UHFFFAOYSA-L 0.000 description 1
- BTMIENSZKMNLRR-UHFFFAOYSA-N tributyl(2-methoxypropyl)phosphanium Chemical compound CCCC[P+](CCCC)(CCCC)CC(C)OC BTMIENSZKMNLRR-UHFFFAOYSA-N 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- ZNEOHLHCKGUAEB-UHFFFAOYSA-N trimethylphenylammonium Chemical compound C[N+](C)(C)C1=CC=CC=C1 ZNEOHLHCKGUAEB-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- GRPURDFRFHUDSP-UHFFFAOYSA-N tris(prop-2-enyl) benzene-1,2,4-tricarboxylate Chemical compound C=CCOC(=O)C1=CC=C(C(=O)OCC=C)C(C(=O)OCC=C)=C1 GRPURDFRFHUDSP-UHFFFAOYSA-N 0.000 description 1
- KJWHEZXBZQXVSA-UHFFFAOYSA-N tris(prop-2-enyl) phosphite Chemical compound C=CCOP(OCC=C)OCC=C KJWHEZXBZQXVSA-UHFFFAOYSA-N 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
- 238000004073 vulcanization Methods 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
- C08F16/00—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 an alcohol, ether, aldehydo, ketonic, acetal or ketal radical
- C08F16/12—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 an alcohol, ether, aldehydo, ketonic, acetal or ketal radical by an ether radical
- C08F16/14—Monomers containing only one unsaturated aliphatic radical
- C08F16/28—Monomers containing nitrogen
-
- 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
-
- 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
- C08F16/00—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 an alcohol, ether, aldehydo, ketonic, acetal or ketal radical
- C08F16/12—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 an alcohol, ether, aldehydo, ketonic, acetal or ketal radical by an ether radical
- C08F16/14—Monomers containing only one unsaturated aliphatic radical
- C08F16/24—Monomers containing halogen
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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Manufacture Of Macromolecular Shaped Articles (AREA)
- Polymerisation Methods In General (AREA)
- Processes Of Treating Macromolecular Substances (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US39924502P | 2002-07-29 | 2002-07-29 | |
| PCT/US2003/023498 WO2004011508A1 (en) | 2002-07-29 | 2003-07-25 | Process for making a fluoroelastomer |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010141955A Division JP2010202888A (ja) | 2002-07-29 | 2010-06-22 | フルオロエラストマーの製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2005534750A true JP2005534750A (ja) | 2005-11-17 |
| JP2005534750A5 JP2005534750A5 (enExample) | 2008-12-25 |
Family
ID=31188561
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2004524923A Ceased JP2005534750A (ja) | 2002-07-29 | 2003-07-25 | フルオロエラストマーの製造方法 |
| JP2010141955A Withdrawn JP2010202888A (ja) | 2002-07-29 | 2010-06-22 | フルオロエラストマーの製造方法 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010141955A Withdrawn JP2010202888A (ja) | 2002-07-29 | 2010-06-22 | フルオロエラストマーの製造方法 |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US7094839B2 (enExample) |
| EP (1) | EP1525233B1 (enExample) |
| JP (2) | JP2005534750A (enExample) |
| KR (1) | KR20050033622A (enExample) |
| CN (1) | CN1315887C (enExample) |
| AT (1) | ATE494312T1 (enExample) |
| AU (1) | AU2003256910A1 (enExample) |
| DE (1) | DE60335627D1 (enExample) |
| RU (1) | RU2005101204A (enExample) |
| WO (1) | WO2004011508A1 (enExample) |
| ZA (1) | ZA200501649B (enExample) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2009500459A (ja) * | 2005-05-25 | 2009-01-08 | ゴア エンタープライズ ホールディングス，インコーポレイティド | 高純度パーフルオロエラストマー複合材およびその製造方法 |
| JP2009185233A (ja) * | 2008-02-08 | 2009-08-20 | Daikin Ind Ltd | シアノ基含有含フッ素エラストマーの製造方法 |
| JP2011514414A (ja) * | 2008-02-29 | 2011-05-06 | スリーエム イノベイティブ プロパティズ カンパニー | 低カルボニル末端基率を有するペルフルオロエラストマー |
| WO2013027851A1 (ja) * | 2011-08-25 | 2013-02-28 | ダイキン工業株式会社 | 全フッ素化飽和炭化水素及び含フッ素界面活性剤を含む組成物 |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7691932B2 (en) | 2004-09-27 | 2010-04-06 | 3M Innovative Properties Company | Method of making a composition and nanocomposites therefrom |
| US7214740B2 (en) * | 2005-05-03 | 2007-05-08 | 3M Innovative Properties Company | Fluorinated ionomers with reduced amounts of carbonyl end groups |
| US7488781B2 (en) * | 2005-05-25 | 2009-02-10 | Gore Enterprise Holdings, Inc. | High purity transparent perfluoroelastomer parts and a process to produce the same |
| US20070100062A1 (en) * | 2005-10-28 | 2007-05-03 | Lyons Donald F | Process for the manufacture of fluoroelastomers having bromine or lodine atom cure sites |
| US20070206364A1 (en) * | 2006-03-02 | 2007-09-06 | Saint-Gobain Performance Plastics Corporation | Methods of forming a flexible circuit board |
| US7754810B2 (en) * | 2007-11-09 | 2010-07-13 | Dupont Performance Elastomers | Process for producing fluoropolymers |
| US20090124755A1 (en) * | 2007-11-09 | 2009-05-14 | Dupont Performance Elastomers L.L.C. | Process for producing fluoropolymers |
| CN101274969B (zh) * | 2007-11-20 | 2010-12-29 | 山东东岳神舟新材料有限公司 | 一种含氟聚合物的微乳液聚合方法 |
| US7977426B2 (en) * | 2008-11-13 | 2011-07-12 | E. I. Du Pont De Nemours And Company | Fluoroalkyl ether sulfonate surfactants |
| TWI482784B (zh) * | 2009-02-13 | 2015-05-01 | Solvay Solexis Spa | 全氟彈性體 |
| GB201007043D0 (en) | 2010-04-28 | 2010-06-09 | 3M Innovative Properties Co | Process for producing ptfe and articles thereof |
| JP5986102B2 (ja) * | 2010-12-17 | 2016-09-06 | スリーエム イノベイティブ プロパティズ カンパニー | マイクロエマルジョン及びマイクロエマルジョンを用いて作製されたフルオロポリマー |
| JP6510411B2 (ja) * | 2012-10-02 | 2019-05-08 | スリーエム イノベイティブ プロパティズ カンパニー | 低いガラス転移温度を有するフルオロポリエーテル系エラストマー |
| CN104356276B (zh) * | 2014-11-06 | 2016-09-07 | 浙江孚诺林化工新材料有限公司 | 一种采用氟醚磺酸盐制备26型氟橡胶的制备方法 |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH03221510A (ja) * | 1989-10-26 | 1991-09-30 | E I Du Pont De Nemours & Co | 臭素およびヨウ素硬化部位を持つペルオキシド―硬化性フルオロエラストマーおよびその製造法 |
| JPH07316234A (ja) * | 1994-05-18 | 1995-12-05 | Ausimont Spa | Ｏリングの製造に特に適した新規の過酸化物硬化性のフッ化エラストマー |
| JPH08301940A (ja) * | 1995-04-28 | 1996-11-19 | Ausimont Spa | 極性末端基が存在しないフルオロエラストマーとその製法 |
| WO1999050319A1 (en) * | 1998-03-25 | 1999-10-07 | Daikin Industries, Ltd. | Method of reducing metal content in fluoroelastomer |
| WO2000022002A1 (en) * | 1998-10-13 | 2000-04-20 | Daikin Industries, Ltd. | Process for producing fluoropolymer |
Family Cites Families (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2793202A (en) * | 1954-05-27 | 1957-05-21 | Kellogg M W Co | Polymerization of trifluorobromoethylene |
| US3345317A (en) * | 1963-04-04 | 1967-10-03 | Thiokol Chemical Corp | Emulsion polymerization of tetrafluoroethylene using trifluorotrichloroethane as emulsion stabilizer |
| US4025481A (en) * | 1971-01-28 | 1977-05-24 | Produits Chimiques Ugine Kuhlmann | Method for the preparation of aqueous dispersions of polytetrafluoroethylene with halogenated hydrocarbon as stabilizing agent |
| US3752787A (en) * | 1972-01-28 | 1973-08-14 | Du Pont | Fluoroelastomer composition containing a triarylphosphorane vulcanization accelerator |
| DK553478A (da) * | 1977-12-14 | 1979-06-15 | Montedison Spa | Vulkaniserbare blandinger paa basis af vinylidenfluoridelastomere samt fremgangsmaade til vulkanisering af saadanne blandinger |
| JPS6165841A (ja) | 1984-09-08 | 1986-04-04 | Daikin Ind Ltd | ポリフルオロアルケニルエ−テルおよびその共重合体 |
| IT1204903B (it) * | 1986-06-26 | 1989-03-10 | Ausimont Spa | Processo di polimerizzazione in dispersione acquosa di monomeri florati |
| US4983697A (en) * | 1989-05-19 | 1991-01-08 | E. I. Du Pont De Nemours And Company | Preparation of cyano-containing perfluoropolymers having iodine curesites |
| US4972038A (en) * | 1989-05-19 | 1990-11-20 | E. I. Du Pont De Nemours And Company | Cyano-containing perfluoropolymers having iodine curesites |
| US5266650A (en) * | 1990-10-11 | 1993-11-30 | Minnesota Mining And Manufacturing Company | Curing fluorocarbon elastomers |
| US5182342A (en) * | 1992-02-28 | 1993-01-26 | E. I. Du Pont De Nemours And Company | Hydrofluorocarbon solvents for fluoromonomer polymerization |
| US5285002A (en) * | 1993-03-23 | 1994-02-08 | Minnesota Mining And Manufacturing Company | Fluorine-containing polymers and preparation and use thereof |
| IT1265461B1 (it) | 1993-12-29 | 1996-11-22 | Ausimont Spa | Fluoroelastomeri comprendenti unita' monomeriche derivanti da una bis-olefina |
| US5447993A (en) * | 1994-04-19 | 1995-09-05 | E. I. Du Pont De Nemours And Company | Perfluoroelastomer curing |
| WO1996022315A1 (en) | 1995-01-18 | 1996-07-25 | W.L. Gore & Associates, Inc. | Microemulsion polymerization systems for fluoromonomers |
| JP3223776B2 (ja) * | 1995-03-31 | 2001-10-29 | 日本メクトロン株式会社 | 含フッ素エラストマー組成物 |
| JP3082626B2 (ja) * | 1995-07-19 | 2000-08-28 | 日本メクトロン株式会社 | 含フッ素エラストマー組成物 |
| IT1276979B1 (it) | 1995-10-20 | 1997-11-03 | Ausimont Spa | Composizioni fluoroelastomeriche |
| US5677389A (en) * | 1996-11-25 | 1997-10-14 | E. I. Du Pont De Nemours | Perfluoroelastomer composition having enhanced curing performance |
| US5877264A (en) * | 1996-11-25 | 1999-03-02 | E. I. Du Pont De Nemours And Company | Fast-curing perfluoroelastomer composition |
| US6281296B1 (en) | 1998-08-10 | 2001-08-28 | Dupont Dow Elastomers L.L.C. | Curable perfluoroelastomer composition |
| US6429258B1 (en) * | 1999-05-20 | 2002-08-06 | E. I. Du Pont De Nemours & Company | Polymerization of fluoromonomers |
| DE19964004A1 (de) | 1999-12-30 | 2001-07-12 | Dyneon Gmbh | Verfahren zur Polymerisation fluorierter Monomerer mit höheren Siedepunkten und geringer Wasserlöslichkeit |
| IT1317847B1 (it) | 2000-02-22 | 2003-07-15 | Ausimont Spa | Processo per la preparazione di dispersioni acquose di fluoropolimeri. |
| IT1318594B1 (it) * | 2000-06-23 | 2003-08-27 | Ausimont Spa | Processo di polimerizzazione di monomeri solfonici. |
| US6730760B2 (en) * | 2001-01-31 | 2004-05-04 | 3M Innovative Properties Company | Perfluoroelastomers having a low glass transition temperature and method of making them |
| US6737489B2 (en) * | 2001-05-21 | 2004-05-18 | 3M Innovative Properties Company | Polymers containing perfluorovinyl ethers and applications for such polymers |
-
2003
- 2003-07-25 JP JP2004524923A patent/JP2005534750A/ja not_active Ceased
- 2003-07-25 WO PCT/US2003/023498 patent/WO2004011508A1/en not_active Ceased
- 2003-07-25 RU RU2005101204/04A patent/RU2005101204A/ru not_active Application Discontinuation
- 2003-07-25 KR KR1020057001546A patent/KR20050033622A/ko not_active Withdrawn
- 2003-07-25 AT AT03771946T patent/ATE494312T1/de not_active IP Right Cessation
- 2003-07-25 EP EP03771946A patent/EP1525233B1/en not_active Expired - Lifetime
- 2003-07-25 CN CNB038183072A patent/CN1315887C/zh not_active Expired - Fee Related
- 2003-07-25 AU AU2003256910A patent/AU2003256910A1/en not_active Abandoned
- 2003-07-25 DE DE60335627T patent/DE60335627D1/de not_active Expired - Lifetime
- 2003-07-25 US US10/627,149 patent/US7094839B2/en not_active Expired - Fee Related
-
2005
- 2005-02-24 ZA ZA200501649A patent/ZA200501649B/xx unknown
-
2010
- 2010-06-22 JP JP2010141955A patent/JP2010202888A/ja not_active Withdrawn
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH03221510A (ja) * | 1989-10-26 | 1991-09-30 | E I Du Pont De Nemours & Co | 臭素およびヨウ素硬化部位を持つペルオキシド―硬化性フルオロエラストマーおよびその製造法 |
| JPH07316234A (ja) * | 1994-05-18 | 1995-12-05 | Ausimont Spa | Ｏリングの製造に特に適した新規の過酸化物硬化性のフッ化エラストマー |
| JPH08301940A (ja) * | 1995-04-28 | 1996-11-19 | Ausimont Spa | 極性末端基が存在しないフルオロエラストマーとその製法 |
| WO1999050319A1 (en) * | 1998-03-25 | 1999-10-07 | Daikin Industries, Ltd. | Method of reducing metal content in fluoroelastomer |
| WO2000022002A1 (en) * | 1998-10-13 | 2000-04-20 | Daikin Industries, Ltd. | Process for producing fluoropolymer |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2009500459A (ja) * | 2005-05-25 | 2009-01-08 | ゴア エンタープライズ ホールディングス，インコーポレイティド | 高純度パーフルオロエラストマー複合材およびその製造方法 |
| JP2009185233A (ja) * | 2008-02-08 | 2009-08-20 | Daikin Ind Ltd | シアノ基含有含フッ素エラストマーの製造方法 |
| JP2011514414A (ja) * | 2008-02-29 | 2011-05-06 | スリーエム イノベイティブ プロパティズ カンパニー | 低カルボニル末端基率を有するペルフルオロエラストマー |
| WO2013027851A1 (ja) * | 2011-08-25 | 2013-02-28 | ダイキン工業株式会社 | 全フッ素化飽和炭化水素及び含フッ素界面活性剤を含む組成物 |
| JP2013060591A (ja) * | 2011-08-25 | 2013-04-04 | Daikin Industries Ltd | 全フッ素化飽和炭化水素及び含フッ素界面活性剤を含む組成物 |
Also Published As
| Publication number | Publication date |
|---|---|
| DE60335627D1 (de) | 2011-02-17 |
| WO2004011508A1 (en) | 2004-02-05 |
| KR20050033622A (ko) | 2005-04-12 |
| US7094839B2 (en) | 2006-08-22 |
| AU2003256910A1 (en) | 2004-02-16 |
| ATE494312T1 (de) | 2011-01-15 |
| CN1315887C (zh) | 2007-05-16 |
| EP1525233B1 (en) | 2011-01-05 |
| CN1671754A (zh) | 2005-09-21 |
| US20040167290A1 (en) | 2004-08-26 |
| RU2005101204A (ru) | 2005-08-10 |
| EP1525233A1 (en) | 2005-04-27 |
| JP2010202888A (ja) | 2010-09-16 |
| ZA200501649B (en) | 2005-09-05 |
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