DE60320285T2 - Peroxidhärtbare fluorelastomere - Google Patents
Peroxidhärtbare fluorelastomere Download PDFInfo
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- DE60320285T2 DE60320285T2 DE60320285T DE60320285T DE60320285T2 DE 60320285 T2 DE60320285 T2 DE 60320285T2 DE 60320285 T DE60320285 T DE 60320285T DE 60320285 T DE60320285 T DE 60320285T DE 60320285 T2 DE60320285 T2 DE 60320285T2
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- 239000000178 monomer Substances 0.000 claims description 172
- 229920001973 fluoroelastomer Polymers 0.000 claims description 97
- 239000000203 mixture Substances 0.000 claims description 88
- 238000006116 polymerization reaction Methods 0.000 claims description 38
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 claims description 38
- BQCIDUSAKPWEOX-UHFFFAOYSA-N 1,1-Difluoroethene Chemical group FC(F)=C BQCIDUSAKPWEOX-UHFFFAOYSA-N 0.000 claims description 32
- 239000003999 initiator Substances 0.000 claims description 28
- OUJSWWHXKJQNMJ-UHFFFAOYSA-N 3,3,4,4-tetrafluoro-4-iodobut-1-ene Chemical group FC(F)(I)C(F)(F)C=C OUJSWWHXKJQNMJ-UHFFFAOYSA-N 0.000 claims description 23
- 239000012986 chain transfer agent Substances 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 20
- 238000004132 cross linking Methods 0.000 claims description 19
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 16
- 229910052731 fluorine Inorganic materials 0.000 claims description 16
- 239000011737 fluorine Substances 0.000 claims description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 150000002170 ethers Chemical class 0.000 claims description 10
- 230000008569 process Effects 0.000 claims description 10
- 150000001336 alkenes Chemical class 0.000 claims description 7
- 239000006185 dispersion Substances 0.000 claims description 7
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 7
- 239000004094 surface-active agent Substances 0.000 claims description 6
- 239000012429 reaction media Substances 0.000 claims description 4
- 150000003254 radicals Chemical class 0.000 claims description 3
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 238000011068 loading method Methods 0.000 claims description 2
- 230000000379 polymerizing effect Effects 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- -1 perfluoro Chemical group 0.000 description 38
- 239000000243 solution Substances 0.000 description 37
- 229920000642 polymer Polymers 0.000 description 35
- 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 23
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 23
- 229910052740 iodine Inorganic materials 0.000 description 23
- 239000011630 iodine Substances 0.000 description 15
- HCDGVLDPFQMKDK-UHFFFAOYSA-N hexafluoropropylene Chemical group FC(F)=C(F)C(F)(F)F HCDGVLDPFQMKDK-UHFFFAOYSA-N 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 239000008367 deionised water Substances 0.000 description 9
- 229910021641 deionized water Inorganic materials 0.000 description 9
- 239000004816 latex Substances 0.000 description 8
- 229920000126 latex Polymers 0.000 description 8
- 150000001451 organic peroxides Chemical class 0.000 description 8
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium peroxydisulfate Substances [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 7
- VAZSKTXWXKYQJF-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)OOS([O-])=O VAZSKTXWXKYQJF-UHFFFAOYSA-N 0.000 description 7
- 229910001870 ammonium persulfate Inorganic materials 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 7
- 229920001971 elastomer Polymers 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- JOQDDLBOAIKFQX-UHFFFAOYSA-N 1,1,2,2,3,3,4,4,5,5,6,6-dodecafluoro-1,6-diiodohexane Chemical compound FC(F)(I)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)I JOQDDLBOAIKFQX-UHFFFAOYSA-N 0.000 description 6
- JILAKKYYZPDQBE-UHFFFAOYSA-N 1,1,2,2,3,3,4,4-octafluoro-1,4-diiodobutane Chemical compound FC(F)(I)C(F)(F)C(F)(F)C(F)(F)I JILAKKYYZPDQBE-UHFFFAOYSA-N 0.000 description 6
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 150000002978 peroxides Chemical class 0.000 description 6
- DMWVYCCGCQPJEA-UHFFFAOYSA-N 2,5-bis(tert-butylperoxy)-2,5-dimethylhexane Chemical compound CC(C)(C)OOC(C)(C)CCC(C)(C)OOC(C)(C)C DMWVYCCGCQPJEA-UHFFFAOYSA-N 0.000 description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 5
- 229910052760 oxygen Inorganic materials 0.000 description 5
- 239000001301 oxygen Substances 0.000 description 5
- 230000000704 physical effect Effects 0.000 description 5
- 239000003505 polymerization initiator Substances 0.000 description 5
- 238000001556 precipitation Methods 0.000 description 5
- 238000012546 transfer Methods 0.000 description 5
- SRDQTCUHAMDAMG-UHFFFAOYSA-N 1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8-hexadecafluoro-1,8-diiodooctane Chemical compound FC(F)(I)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)I SRDQTCUHAMDAMG-UHFFFAOYSA-N 0.000 description 4
- 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 4
- UUAGAQFQZIEFAH-UHFFFAOYSA-N chlorotrifluoroethylene Chemical group FC(F)=C(F)Cl UUAGAQFQZIEFAH-UHFFFAOYSA-N 0.000 description 4
- 238000007906 compression Methods 0.000 description 4
- 230000006835 compression Effects 0.000 description 4
- PYLIXCKOHOHGKQ-UHFFFAOYSA-L disodium;hydrogen phosphate;heptahydrate Chemical compound O.O.O.O.O.O.O.[Na+].[Na+].OP([O-])([O-])=O PYLIXCKOHOHGKQ-UHFFFAOYSA-L 0.000 description 4
- 239000000945 filler Substances 0.000 description 4
- 239000004615 ingredient Substances 0.000 description 4
- 238000000465 moulding Methods 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 238000004073 vulcanization Methods 0.000 description 4
- 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
- QBEWJJSQJWLVAI-UHFFFAOYSA-N 1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10-icosafluoro-1,10-diiododecane Chemical compound FC(F)(I)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)I QBEWJJSQJWLVAI-UHFFFAOYSA-N 0.000 description 3
- YKTNISGZEGZHIS-UHFFFAOYSA-N 2-$l^{1}-oxidanyloxy-2-methylpropane Chemical group CC(C)(C)O[O] YKTNISGZEGZHIS-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- 238000007720 emulsion polymerization reaction Methods 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- XUCNUKMRBVNAPB-UHFFFAOYSA-N fluoroethene Chemical compound FC=C XUCNUKMRBVNAPB-UHFFFAOYSA-N 0.000 description 3
- GRLPQNLYRHEGIJ-UHFFFAOYSA-J potassium aluminium sulfate Chemical compound [Al+3].[K+].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O GRLPQNLYRHEGIJ-UHFFFAOYSA-J 0.000 description 3
- 238000000518 rheometry Methods 0.000 description 3
- 238000010998 test method Methods 0.000 description 3
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- 239000006057 Non-nutritive feed additive Substances 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 230000032683 aging Effects 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- DIZPMCHEQGEION-UHFFFAOYSA-H aluminium sulfate (anhydrous) Chemical compound [Al+3].[Al+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O DIZPMCHEQGEION-UHFFFAOYSA-H 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- 239000003638 chemical reducing agent Substances 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 230000009477 glass transition Effects 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229910000000 metal hydroxide Inorganic materials 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- 239000006174 pH buffer Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
- 239000004071 soot Substances 0.000 description 2
- KDGNCLDCOVTOCS-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy propan-2-yl carbonate Chemical compound CC(C)OC(=O)OOC(C)(C)C KDGNCLDCOVTOCS-UHFFFAOYSA-N 0.000 description 1
- RIPYNJLMMFGZSX-UHFFFAOYSA-N (5-benzoylperoxy-2,5-dimethylhexan-2-yl) benzenecarboperoxoate Chemical compound C=1C=CC=CC=1C(=O)OOC(C)(C)CCC(C)(C)OOC(=O)C1=CC=CC=C1 RIPYNJLMMFGZSX-UHFFFAOYSA-N 0.000 description 1
- DMUPYMORYHFFCT-UPHRSURJSA-N (z)-1,2,3,3,3-pentafluoroprop-1-ene Chemical compound F\C=C(/F)C(F)(F)F DMUPYMORYHFFCT-UPHRSURJSA-N 0.000 description 1
- BLKRGXCGFRXRNQ-SNAWJCMRSA-N (z)-3-carbonoperoxoyl-4,4-dimethylpent-2-enoic acid Chemical compound OC(=O)/C=C(C(C)(C)C)\C(=O)OO BLKRGXCGFRXRNQ-SNAWJCMRSA-N 0.000 description 1
- WIEYKFZUVTYEIY-UHFFFAOYSA-N 1,1,2,2,3,3-hexafluoro-1,3-diiodopropane Chemical compound FC(F)(I)C(F)(F)C(F)(F)I WIEYKFZUVTYEIY-UHFFFAOYSA-N 0.000 description 1
- NALFRYPTRXKZPN-UHFFFAOYSA-N 1,1-bis(tert-butylperoxy)-3,3,5-trimethylcyclohexane Chemical compound CC1CC(C)(C)CC(OOC(C)(C)C)(OOC(C)(C)C)C1 NALFRYPTRXKZPN-UHFFFAOYSA-N 0.000 description 1
- HSLFISVKRDQEBY-UHFFFAOYSA-N 1,1-bis(tert-butylperoxy)cyclohexane Chemical compound CC(C)(C)OOC1(OOC(C)(C)C)CCCCC1 HSLFISVKRDQEBY-UHFFFAOYSA-N 0.000 description 1
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- MPJPKEMZYOAIRN-UHFFFAOYSA-N 1,3,5-tris(2-methylprop-2-enyl)-1,3,5-triazinane-2,4,6-trione Chemical compound CC(=C)CN1C(=O)N(CC(C)=C)C(=O)N(CC(C)=C)C1=O MPJPKEMZYOAIRN-UHFFFAOYSA-N 0.000 description 1
- 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 1
- IPJGAEWUPXWFPL-UHFFFAOYSA-N 1-[3-(2,5-dioxopyrrol-1-yl)phenyl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1=CC=CC(N2C(C=CC2=O)=O)=C1 IPJGAEWUPXWFPL-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
- CWJHMZONBMHMEI-UHFFFAOYSA-N 1-tert-butylperoxy-3-propan-2-ylbenzene Chemical compound CC(C)C1=CC=CC(OOC(C)(C)C)=C1 CWJHMZONBMHMEI-UHFFFAOYSA-N 0.000 description 1
- ZPGMWBFCBUKITA-UHFFFAOYSA-N 2,2,3-trichloro-1,1,1,3,4,4,4-heptafluorobutane Chemical compound FC(F)(F)C(F)(Cl)C(Cl)(Cl)C(F)(F)F ZPGMWBFCBUKITA-UHFFFAOYSA-N 0.000 description 1
- JPOUDZAPLMMUES-UHFFFAOYSA-N 2,2-bis(tert-butylperoxy)octane Chemical compound CCCCCCC(C)(OOC(C)(C)C)OOC(C)(C)C JPOUDZAPLMMUES-UHFFFAOYSA-N 0.000 description 1
- BJELTSYBAHKXRW-UHFFFAOYSA-N 2,4,6-triallyloxy-1,3,5-triazine Chemical compound C=CCOC1=NC(OCC=C)=NC(OCC=C)=N1 BJELTSYBAHKXRW-UHFFFAOYSA-N 0.000 description 1
- KRDXTHSSNCTAGY-UHFFFAOYSA-N 2-cyclohexylpyrrolidine Chemical compound C1CCNC1C1CCCCC1 KRDXTHSSNCTAGY-UHFFFAOYSA-N 0.000 description 1
- QLKDMIUEWFNEPV-UHFFFAOYSA-N 4,5,6,7-Tetrachloro-2-trifluoromethylbenzimidazole Chemical compound ClC1=C(Cl)C(Cl)=C2NC(C(F)(F)F)=NC2=C1Cl QLKDMIUEWFNEPV-UHFFFAOYSA-N 0.000 description 1
- IXIMRXNEIJHZCJ-UHFFFAOYSA-N 4-propoxy-1-(4-propoxybut-1-enoxy)but-1-ene Chemical compound C(CC)OCCC=COC=CCCOCCC IXIMRXNEIJHZCJ-UHFFFAOYSA-N 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 239000004971 Cross linker Substances 0.000 description 1
- 239000004641 Diallyl-phthalate Substances 0.000 description 1
- UAUDZVJPLUQNMU-UHFFFAOYSA-N Erucasaeureamid Natural products CCCCCCCCC=CCCCCCCCCCCCC(N)=O UAUDZVJPLUQNMU-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
- 239000005909 Kieselgur Substances 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- 239000008351 acetate buffer Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 235000011126 aluminium potassium sulphate Nutrition 0.000 description 1
- CEGOLXSVJUTHNZ-UHFFFAOYSA-K aluminium tristearate Chemical compound [Al+3].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CEGOLXSVJUTHNZ-UHFFFAOYSA-K 0.000 description 1
- 229940063655 aluminum stearate Drugs 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
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- 238000010923 batch production Methods 0.000 description 1
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- 230000005540 biological transmission Effects 0.000 description 1
- QUDWYFHPNIMBFC-UHFFFAOYSA-N bis(prop-2-enyl) benzene-1,2-dicarboxylate Chemical compound C=CCOC(=O)C1=CC=CC=C1C(=O)OCC=C QUDWYFHPNIMBFC-UHFFFAOYSA-N 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- WUKWITHWXAAZEY-UHFFFAOYSA-L calcium difluoride Chemical compound [F-].[F-].[Ca+2] WUKWITHWXAAZEY-UHFFFAOYSA-L 0.000 description 1
- 229910001634 calcium fluoride Inorganic materials 0.000 description 1
- 239000000378 calcium silicate Substances 0.000 description 1
- 229910052918 calcium silicate Inorganic materials 0.000 description 1
- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
- 239000008116 calcium stearate Substances 0.000 description 1
- 235000013539 calcium stearate Nutrition 0.000 description 1
- OYACROKNLOSFPA-UHFFFAOYSA-N calcium;dioxido(oxo)silane Chemical compound [Ca+2].[O-][Si]([O-])=O OYACROKNLOSFPA-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
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- 239000004927 clay Substances 0.000 description 1
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- 238000011109 contamination Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229920006037 cross link polymer Polymers 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 230000002939 deleterious effect Effects 0.000 description 1
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- 238000000113 differential scanning calorimetry Methods 0.000 description 1
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 1
- 229910000397 disodium phosphate Inorganic materials 0.000 description 1
- 235000019800 disodium phosphate Nutrition 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000806 elastomer Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- UAUDZVJPLUQNMU-KTKRTIGZSA-N erucamide Chemical compound CCCCCCCC\C=C/CCCCCCCCCCCC(N)=O UAUDZVJPLUQNMU-KTKRTIGZSA-N 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 238000002270 exclusion chromatography Methods 0.000 description 1
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- 238000001914 filtration Methods 0.000 description 1
- 229920002313 fluoropolymer Polymers 0.000 description 1
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- 239000008246 gaseous mixture Substances 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 239000004519 grease Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- YOBAEOGBNPPUQV-UHFFFAOYSA-N iron;trihydrate Chemical compound O.O.O.[Fe].[Fe] YOBAEOGBNPPUQV-UHFFFAOYSA-N 0.000 description 1
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000010907 mechanical stirring Methods 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 150000004692 metal hydroxides Chemical class 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- BLYOHBPLFYXHQA-UHFFFAOYSA-N n,n-bis(prop-2-enyl)prop-2-enamide Chemical compound C=CCN(CC=C)C(=O)C=C BLYOHBPLFYXHQA-UHFFFAOYSA-N 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- DYUWTXWIYMHBQS-UHFFFAOYSA-N n-prop-2-enylprop-2-en-1-amine Chemical compound C=CCNCC=C DYUWTXWIYMHBQS-UHFFFAOYSA-N 0.000 description 1
- 230000006855 networking Effects 0.000 description 1
- 238000009828 non-uniform distribution Methods 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 125000006551 perfluoro alkylene group Chemical group 0.000 description 1
- 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 1
- 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 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229940050271 potassium alum Drugs 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 238000010058 rubber compounding Methods 0.000 description 1
- 239000003566 sealing material Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- RYYKJJJTJZKILX-UHFFFAOYSA-M sodium octadecanoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCC([O-])=O RYYKJJJTJZKILX-UHFFFAOYSA-M 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- MHSKRLJMQQNJNC-UHFFFAOYSA-N terephthalamide Chemical compound NC(=O)C1=CC=C(C(N)=O)C=C1 MHSKRLJMQQNJNC-UHFFFAOYSA-N 0.000 description 1
- PNWOTXLVRDKNJA-UHFFFAOYSA-N tert-butylperoxybenzene Chemical compound CC(C)(C)OOC1=CC=CC=C1 PNWOTXLVRDKNJA-UHFFFAOYSA-N 0.000 description 1
- TXEYQDLBPFQVAA-UHFFFAOYSA-N tetrafluoromethane Chemical compound FC(F)(F)F TXEYQDLBPFQVAA-UHFFFAOYSA-N 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 235000010215 titanium dioxide Nutrition 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
- 229940070710 valerate Drugs 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000010456 wollastonite Substances 0.000 description 1
- 229910052882 wollastonite Inorganic materials 0.000 description 1
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 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
- C08F214/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen
- C08F214/18—Monomers containing fluorine
- C08F214/22—Vinylidene fluoride
-
- 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
- C08F214/26—Tetrafluoroethene
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)
- Compositions Of Macromolecular Compounds (AREA)
- Processes Of Treating Macromolecular Substances (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US193435 | 1998-11-17 | ||
| US10/193,435 US6646077B1 (en) | 2002-07-11 | 2002-07-11 | Peroxide curable fluoroelastomers |
| PCT/US2003/021247 WO2004007577A1 (en) | 2002-07-11 | 2003-07-02 | Peroxide curable fluoroelastomers |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE60320285D1 DE60320285D1 (de) | 2008-05-21 |
| DE60320285T2 true DE60320285T2 (de) | 2009-05-14 |
Family
ID=29400912
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE60320285T Expired - Lifetime DE60320285T2 (de) | 2002-07-11 | 2003-07-02 | Peroxidhärtbare fluorelastomere |
Country Status (8)
| Country | Link |
|---|---|
| US (2) | US6646077B1 (enExample) |
| EP (1) | EP1551889B1 (enExample) |
| JP (1) | JP4795685B2 (enExample) |
| KR (1) | KR101026908B1 (enExample) |
| CN (1) | CN1297578C (enExample) |
| DE (1) | DE60320285T2 (enExample) |
| TW (1) | TWI291965B (enExample) |
| WO (1) | WO2004007577A1 (enExample) |
Families Citing this family (42)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2005104992A (ja) | 2003-01-24 | 2005-04-21 | Daikin Ind Ltd | 加硫可能な含フッ素エラストマーの製造方法 |
| EP1751843B1 (en) * | 2003-08-29 | 2012-09-19 | SRI International | Electroactive polymer pre-strain |
| ATE413418T1 (de) * | 2004-09-09 | 2008-11-15 | 3M Innovative Properties Co | Fluoropolymer zur herstellung von einem fluoroelastomer |
| US7943685B2 (en) * | 2005-04-13 | 2011-05-17 | R.T. Vanderbilt Company, Inc. | Composition and method for curing latex compounds |
| US8932706B2 (en) | 2005-10-27 | 2015-01-13 | Multi-Color Corporation | Laminate with a heat-activatable expandable layer |
| CN100420701C (zh) * | 2005-12-23 | 2008-09-24 | 上海三爱富新材料股份有限公司 | 氟弹性体及其制备方法 |
| WO2009006318A1 (en) | 2007-06-29 | 2009-01-08 | Artificial Muscle, Inc. | Electroactive polymer transducers for sensory feedback applications |
| KR101530105B1 (ko) * | 2007-09-14 | 2015-06-18 | 쓰리엠 이노베이티브 프로퍼티즈 캄파니 | 초저점도 요오드 함유 무정형 플루오로중합체 |
| US20090227726A1 (en) * | 2008-03-04 | 2009-09-10 | Dupont Performance Elastomers L.L.C. | Peroxide curable fluoroelastomer compositions and articles made therefrom |
| CN103131106A (zh) | 2008-03-27 | 2013-06-05 | 大金工业株式会社 | 过氧化物交联类含氟弹性体组合物 |
| US20090292094A1 (en) * | 2008-05-21 | 2009-11-26 | E. I. Dupont De Nemours And Company | Fluoropolymer Composition |
| US20090291283A1 (en) * | 2008-05-21 | 2009-11-26 | E.I. Dupont De Nemours And Company | Fluoropolymer films |
| US8153198B2 (en) * | 2008-05-21 | 2012-04-10 | E I Du Pont De Nemours And Company | Fluoropolymer solutions, coatings and coated articles |
| TWI482784B (zh) * | 2009-02-13 | 2015-05-01 | Solvay Solexis Spa | 全氟彈性體 |
| EP2373704A4 (en) * | 2009-03-05 | 2012-10-17 | Daikin Ind Ltd | FLUOROELASTOMER, CURABLE COMPOSITION, AND CURED RUBBER ARTICLE |
| EP2239793A1 (de) | 2009-04-11 | 2010-10-13 | Bayer MaterialScience AG | Elektrisch schaltbarer Polymerfilmaufbau und dessen Verwendung |
| US9553254B2 (en) | 2011-03-01 | 2017-01-24 | Parker-Hannifin Corporation | Automated manufacturing processes for producing deformable polymer devices and films |
| KR20140019801A (ko) | 2011-03-22 | 2014-02-17 | 바이엘 인텔렉쳐 프로퍼티 게엠베하 | 전기활성 중합체 작동기 렌티큘라 시스템 |
| US20130053519A1 (en) * | 2011-08-31 | 2013-02-28 | E. I. Du Pont De Nemours And Company | Acid resistant fluoroelastomer compositions |
| US20130158154A1 (en) * | 2011-12-15 | 2013-06-20 | E.I.Du Pont De Nemours And Company | Coagent for free radical curing fluoroelastomers |
| CN102558719B (zh) * | 2011-12-29 | 2014-07-02 | 中昊晨光化工研究院 | 一种耐低温含氟弹性体及其制备方法 |
| US9876160B2 (en) | 2012-03-21 | 2018-01-23 | Parker-Hannifin Corporation | Roll-to-roll manufacturing processes for producing self-healing electroactive polymer devices |
| US9761790B2 (en) | 2012-06-18 | 2017-09-12 | Parker-Hannifin Corporation | Stretch frame for stretching process |
| EP2909162B1 (en) | 2012-10-17 | 2016-09-21 | 3M Innovative Properties Company | Method of making alpha, omega-diiodoperfluoroalkanes |
| US9590193B2 (en) | 2012-10-24 | 2017-03-07 | Parker-Hannifin Corporation | Polymer diode |
| EP2935356B1 (en) | 2012-12-19 | 2016-10-05 | 3M Innovative Properties Company | Method of making fluoropolymers with a polyiodide, compositions and articles thereof |
| CN103342772B (zh) | 2013-07-12 | 2015-08-05 | 中昊晨光化工研究院有限公司 | 一种可用过氧化物硫化的含氟弹性体的制备方法 |
| CN103755856A (zh) * | 2013-12-16 | 2014-04-30 | 江苏梅兰化工有限公司 | 一种用于过氧化物硫化氟弹性体的生产方法 |
| CN103709306A (zh) * | 2013-12-30 | 2014-04-09 | 江苏梅兰化工有限公司 | 一种过氧化物硫化氟橡胶的纳米乳液及其聚合方法 |
| CN106103572B (zh) | 2014-03-06 | 2019-09-27 | 3M创新有限公司 | 高度氟化弹性体 |
| JP6987740B2 (ja) | 2015-07-13 | 2022-01-05 | スリーエム イノベイティブ プロパティズ カンパニー | フッ素化ブロックコポリマー |
| EP3365389A4 (en) | 2015-10-23 | 2019-05-29 | 3M Innovative Properties Company | COMPOSITION WITH AMORPHIC FLUOROPOLYMER AND FLUOROON PLASTIC PARTICLES AND METHOD FOR THE PRODUCTION THEREOF |
| EP3408320A1 (en) | 2016-01-26 | 2018-12-05 | E. I. du Pont de Nemours and Company | Fluoroelastomer compounds |
| CN109476875A (zh) * | 2016-06-13 | 2019-03-15 | 索尔维特殊聚合物意大利有限公司 | 可固化的氟弹性体组合物 |
| WO2018136332A1 (en) * | 2017-01-18 | 2018-07-26 | 3M Innovative Properties Company | Fluorinated block copolymers derived from cure-site monomers |
| US11267922B2 (en) | 2017-01-18 | 2022-03-08 | 3M Innovative Properties Company | Fluorinated block copolymers derived from nitrile cure-site monomers |
| EP3571247A4 (en) | 2017-01-18 | 2020-11-11 | 3M Innovative Properties Company | FLUORINE SEQUENCED COPOLYMERS |
| WO2018225789A1 (ja) * | 2017-06-06 | 2018-12-13 | 日本ゼオン株式会社 | ゴム架橋物およびその製造方法 |
| WO2019111824A1 (ja) * | 2017-12-06 | 2019-06-13 | Ａｇｃ株式会社 | 含フッ素弾性共重合体及び含フッ素弾性共重合体の製造方法 |
| CN111057178B (zh) * | 2019-12-31 | 2022-03-29 | 山东华夏神舟新材料有限公司 | 低压变含氟弹性体的制备方法 |
| WO2024110375A1 (en) | 2022-11-22 | 2024-05-30 | Dupont Specialty Products Operations Sarl | Perfluoroelastomer compounds |
| CN120535393A (zh) * | 2024-02-26 | 2025-08-26 | 六安屹珹新材料科技有限公司 | 含烯烃的硫化点单体、其制备方法和氟聚合物弹性体 |
Family Cites Families (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3839305A (en) * | 1970-12-14 | 1974-10-01 | Du Pont | Method of making vinylidene fluoride copolymers |
| JPS53125491A (en) | 1977-04-08 | 1978-11-01 | Daikin Ind Ltd | Fluorine-containing polymer easily curable and its curable composition |
| CA1248286A (en) | 1984-08-09 | 1989-01-03 | Paul G. Bekiarian | Improved fluoropolymer |
| JPS6155238A (ja) * | 1984-08-27 | 1986-03-19 | 敷島紡績株式会社 | ル−ムワインダ−残糸木管糸端引き出し方法 |
| US4529759A (en) | 1984-12-07 | 1985-07-16 | E. I. Du Pont De Nemours And Company | Peroxide-curable brominated or iodinated fluoroelastomer composition containing an N,N,N',N'-tetrasubstituted 1,8-diaminonaphthalene |
| US4694045A (en) | 1985-12-11 | 1987-09-15 | E. I. Du Pont De Nemours And Company | Base resistant fluoroelastomers |
| DE3677076D1 (de) * | 1985-07-12 | 1991-02-28 | Du Pont | Fluorelastomere. |
| US5384374A (en) * | 1991-01-11 | 1995-01-24 | Minnesota Mining And Manufacturing Company | Curing fluorocarbon elastomers |
| JPH04288305A (ja) | 1991-03-15 | 1992-10-13 | Nippon Mektron Ltd | パーオキサイド加硫可能な含フッ素エラストマ−の製造方法 |
| US5214106A (en) | 1991-05-22 | 1993-05-25 | E. I. Du Pont De Nemours And Company | Cured fluoroelastomer compositions |
| JP3259317B2 (ja) | 1992-02-14 | 2002-02-25 | 日本メクトロン株式会社 | パ−オキサイド加硫可能な含フッ素エラストマ−の製造方法 |
| IT1265461B1 (it) | 1993-12-29 | 1996-11-22 | Ausimont Spa | Fluoroelastomeri comprendenti unita' monomeriche derivanti da una bis-olefina |
| IT1269514B (it) * | 1994-05-18 | 1997-04-01 | Ausimont Spa | Fluoroelastomeri vulcanizzabili per via perossidica,particolarmente adatti per la fabbricazione di o-ring |
| JP3327016B2 (ja) * | 1994-12-06 | 2002-09-24 | ダイキン工業株式会社 | 低温シール性に優れたフッ素ゴム共重合体及びその硬化用組成物 |
| WO1997024381A1 (en) * | 1995-12-28 | 1997-07-10 | Daikin Industries, Ltd. | Fluorine-containing elastic copolymers, curable composition containing the same and sealant made therefrom |
| EP0845482B1 (en) | 1996-11-29 | 2000-02-02 | Nippon Mektron, Ltd. | Process for producing fluorine-containing elastomer |
| US6191208B1 (en) * | 1998-05-20 | 2001-02-20 | Dupont Dow Elastomers L.L.S. | Thermally stable perfluoroelastomer composition |
| US6277937B1 (en) * | 2000-02-17 | 2001-08-21 | Dupont Dow Elastomers, L.L.C. | Process for producing fluorelastomers |
| US6774164B2 (en) * | 2000-09-22 | 2004-08-10 | Dupont Dow Elastomers L.L.C. | Process for producing fluoroelastomers with fluorinated anionic surfactants |
-
2002
- 2002-07-11 US US10/193,435 patent/US6646077B1/en not_active Expired - Lifetime
-
2003
- 2003-06-24 TW TW092117145A patent/TWI291965B/zh not_active IP Right Cessation
- 2003-07-02 JP JP2004521548A patent/JP4795685B2/ja not_active Expired - Lifetime
- 2003-07-02 EP EP03751786A patent/EP1551889B1/en not_active Expired - Lifetime
- 2003-07-02 CN CNB038160153A patent/CN1297578C/zh not_active Expired - Lifetime
- 2003-07-02 DE DE60320285T patent/DE60320285T2/de not_active Expired - Lifetime
- 2003-07-02 KR KR1020057000431A patent/KR101026908B1/ko not_active Expired - Fee Related
- 2003-07-02 WO PCT/US2003/021247 patent/WO2004007577A1/en not_active Ceased
- 2003-09-25 US US10/671,130 patent/US20040092684A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| JP4795685B2 (ja) | 2011-10-19 |
| WO2004007577A1 (en) | 2004-01-22 |
| TW200400977A (en) | 2004-01-16 |
| EP1551889A1 (en) | 2005-07-13 |
| KR20050025335A (ko) | 2005-03-14 |
| CN1297578C (zh) | 2007-01-31 |
| US20040092684A1 (en) | 2004-05-13 |
| CN1665852A (zh) | 2005-09-07 |
| TWI291965B (en) | 2008-01-01 |
| DE60320285D1 (de) | 2008-05-21 |
| EP1551889B1 (en) | 2008-04-09 |
| KR101026908B1 (ko) | 2011-04-04 |
| US6646077B1 (en) | 2003-11-11 |
| JP2005532465A (ja) | 2005-10-27 |
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