DE60320285T2 - Peroxidhärtbare fluorelastomere - Google Patents

Peroxidhärtbare fluorelastomere Download PDF

Info

Publication number: DE60320285T2
Authority: DE; Germany
Prior art keywords: reactor; monomer; amount; monomer mixture; weight
Prior art date: 2002-07-11
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired - Lifetime

Application number

DE60320285T

Other languages

German (de)

English (en)

Other versions

DE60320285D1 (de

Inventor

Donald Frederick Wilmington LYONS

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

DuPont Performance Elastomers LLC

Original Assignee

DuPont Dow Elastomers LLC

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2002-07-11

Filing date

2003-07-02

Publication date

2009-05-14

2003-07-02 Application filed by DuPont Dow Elastomers LLC filed Critical DuPont Dow Elastomers LLC

2008-05-21 Application granted granted Critical

2008-05-21 Publication of DE60320285D1 publication Critical patent/DE60320285D1/de

2009-05-14 Publication of DE60320285T2 publication Critical patent/DE60320285T2/de

2023-07-03 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

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
239000012298 atmosphere Substances 0.000 description 1
238000010923 batch production Methods 0.000 description 1
235000019400 benzoyl peroxide Nutrition 0.000 description 1
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
230000008859 change Effects 0.000 description 1
150000005827 chlorofluoro hydrocarbons Chemical class 0.000 description 1
239000004927 clay Substances 0.000 description 1
238000013329 compounding Methods 0.000 description 1
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
239000000706 filtrate Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
229920002313 fluoropolymer Polymers 0.000 description 1
239000004811 fluoropolymer Substances 0.000 description 1
238000009472 formulation Methods 0.000 description 1
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)

DE60320285T 2002-07-11 2003-07-02 Peroxidhärtbare fluorelastomere Expired - Lifetime DE60320285T2 (de)

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 (2)
EP (1)	EP1551889B1 (2)
JP (1)	JP4795685B2 (2)
KR (1)	KR101026908B1 (2)
CN (1)	CN1297578C (2)
DE (1)	DE60320285T2 (2)
TW (1)	TWI291965B (2)
WO (1)	WO2004007577A1 (2)

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KR20150031285A (ko)	2012-06-18	2015-03-23	바이엘 인텔렉쳐 프로퍼티 게엠베하	연신 공정을 위한 연신 프레임
WO2014062450A2 (en)	2012-10-17	2014-04-24	3M Innovative Properties Company	Method of making alpha, omega-diiodoperfluoroalkanes
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US9556298B2 (en)	2012-12-19	2017-01-31	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
KR102279977B1 (ko)	2014-03-06	2021-07-22	쓰리엠 이노베이티브 프로퍼티즈 컴파니	고도 플루오르화 엘라스토머
WO2017011379A1 (en)	2015-07-13	2017-01-19	3M Innovative Properties Company	Fluorinated block copolymers
SG11201803368SA (en)	2015-10-23	2018-05-30	3M Innovative Properties Co	Composition including amorphous fluoropolymer and fluoroplastic particles and methods of making the same
WO2017132706A1 (en)	2016-01-26	2017-08-03	E I Du Pont De Nemours And Company	Fluoroelastomer compounds
US20190161607A1 (en) *	2016-06-13	2019-05-30	Solvay Specialty Polymers Italy S.P.A.	Curable fluoroelastomer composition
WO2018136331A1 (en)	2017-01-18	2018-07-26	3M Innovative Properties Company	Fluorinated block copolymers
WO2018136332A1 (en) *	2017-01-18	2018-07-26	3M Innovative Properties Company	Fluorinated block copolymers derived from cure-site monomers
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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 KR KR1020057000431A patent/KR101026908B1/ko not_active Expired - Fee Related
- 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 DE DE60320285T patent/DE60320285T2/de not_active Expired - Lifetime
- 2003-07-02 WO PCT/US2003/021247 patent/WO2004007577A1/en not_active Ceased
- 2003-07-02 CN CNB038160153A patent/CN1297578C/zh not_active Expired - Lifetime
- 2003-09-25 US US10/671,130 patent/US20040092684A1/en not_active Abandoned

Also Published As

Publication number	Publication date
CN1665852A (zh)	2005-09-07
JP2005532465A (ja)	2005-10-27
DE60320285D1 (de)	2008-05-21
US6646077B1 (en)	2003-11-11
JP4795685B2 (ja)	2011-10-19
EP1551889A1 (en)	2005-07-13
WO2004007577A1 (en)	2004-01-22
KR101026908B1 (ko)	2011-04-04
TW200400977A (en)	2004-01-16
EP1551889B1 (en)	2008-04-09
KR20050025335A (ko)	2005-03-14
TWI291965B (en)	2008-01-01
CN1297578C (zh)	2007-01-31
US20040092684A1 (en)	2004-05-13

Legal Events

Date	Code	Title	Description
2009-04-30	8364	No opposition during term of opposition

Publication	Publication Date	Title
DE60320285T2 (de)	2009-05-14	Peroxidhärtbare fluorelastomere
DE3818349C2 (de)	1996-03-28	Verfahren zur Herstellung von mittels Peroxid vulkanisierbaren, Fluor enthaltenden Elastomeren
DE4203575B4 (de)	2005-03-24	Verfahren zur Herstellung von mittels Peroxid vulkanisierbaren, Fluor enthaltenden Elastomeren
DE69005519T2 (de)	1994-05-11	Mit Peroxid härtbare Fluorelastomere mit Brom- und Jod-Vernetzungspunkten und ihre Herstellung.
DE69212168T2 (de)	1996-12-19	Vernetzte fluoroelastomere zusammensetzungen
DE60203384T2 (de)	2006-04-20	Härtbare basenresistente fluoroelastomere
DE4244434B4 (de)	2006-02-09	Verfahren zur Herstellung von mittels Peroxid vulkanisierbaren, Fluor enthaltenden Elastomeren
DE3715210C2 (de)	1996-09-05	Fluor enthaltende Polymere und härtbare Zusammensetzungen, welche diese enthalten
DE60216889T3 (de)	2020-10-22	Vernetzbare Fluorelastomere
DE69003506T2 (de)	1994-02-17	Peroxidhärtbare Fluor- und Chlorfluorelastomere mit Brom und Jod als Härtungszentren und ihre Herstellung.
DE69013249T2 (de)	1995-02-23	Fluorelastomere mit verbesserter Verarbeitbarkeit und Verfahren zu ihrer Herstellung.
DE2612360C3 (de)	1979-04-19	Wärmehärtbare Masse auf Basis von Mischpolymerisaten
DE69013913T2 (de)	1995-03-09	Herstellung von cyanidhaltigen perfluorpolymeren mit iodatomen als vernetzungsstellen.
DE69013915T2 (de)	1995-03-09	Cyanidhaltige perfluorpolymere mit iodatomen als vernetzungsstellen.
DE69013912T2 (de)	1995-03-09	Bromhaltige perfluorpolymere mit iodatomen als vernetzungsstellen.
DE2940686C2 (2)	1990-06-28
DE60205841T2 (de)	2006-05-18	Perfluorelastomere
DE3587350T2 (de)	1993-12-16	Vulkanisierbare Zusammensetzung aus elastomerischen Vinylidenfluoridmischpolymerisaten.
DE3710818C2 (de)	1993-10-21	Verfahren zur Herstellung von mittels Peroxid vulkanisierbaren, Fluor enthaltenden Elastomeren
DE60201987T2 (de)	2006-03-02	Härtbare basenbeständige fluorelastomere
DE60128833T2 (de)	2008-02-07	Perfluoroelastomere mit niedriger glasübergangstemperatur und deren herstelungsverfahren
EP0929584B1 (de)	2001-05-09	Flüssig-fluorkautschuk
DE69210901T2 (de)	1996-10-10	Ionisch vulkanisierbare, fluorelastomere Copolymere
DE69716289T2 (de)	2003-06-26	Sulfonierte perfluorelastomer-zusammensetzungen mit verbesserter verarbeitbarkeit
DE3710819C2 (de)	1994-11-24	Verfahren zur Herstellung von mittels Peroxid vulkanisierbaren, Fluor enthaltenden Elastomeren