DE3818349C2 - Verfahren zur Herstellung von mittels Peroxid vulkanisierbaren, Fluor enthaltenden Elastomeren - Google Patents
Verfahren zur Herstellung von mittels Peroxid vulkanisierbaren, Fluor enthaltenden ElastomerenInfo
- Publication number
- DE3818349C2 DE3818349C2 DE3818349A DE3818349A DE3818349C2 DE 3818349 C2 DE3818349 C2 DE 3818349C2 DE 3818349 A DE3818349 A DE 3818349A DE 3818349 A DE3818349 A DE 3818349A DE 3818349 C2 DE3818349 C2 DE 3818349C2
- Authority
- DE
- Germany
- Prior art keywords
- fluorine
- bromo
- iodine
- bromine
- iodo
- Prior art date
- 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
Links
- 229910052731 fluorine Inorganic materials 0.000 title claims description 69
- 239000011737 fluorine Substances 0.000 title claims description 69
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 title claims description 68
- 229920001971 elastomer Polymers 0.000 title claims description 48
- 239000000806 elastomer Substances 0.000 title claims description 42
- 238000000034 method Methods 0.000 title claims description 23
- 230000008569 process Effects 0.000 title claims description 10
- 150000002978 peroxides Chemical class 0.000 title claims description 7
- 238000004519 manufacturing process Methods 0.000 title description 8
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 30
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 27
- 229910052794 bromium Inorganic materials 0.000 claims description 27
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 26
- 229910052740 iodine Inorganic materials 0.000 claims description 26
- 239000011630 iodine Substances 0.000 claims description 26
- 150000001875 compounds Chemical class 0.000 claims description 23
- 150000001336 alkenes Chemical class 0.000 claims description 20
- QZGNGBWAMYFUST-UHFFFAOYSA-N 2-bromo-1,1-difluoroethene Chemical group FC(F)=CBr QZGNGBWAMYFUST-UHFFFAOYSA-N 0.000 claims description 13
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 239000003505 polymerization initiator Substances 0.000 claims description 8
- 238000007334 copolymerization reaction Methods 0.000 claims description 5
- KYKAJFCTULSVSH-UHFFFAOYSA-N chloro(fluoro)methane Chemical group F[C]Cl KYKAJFCTULSVSH-UHFFFAOYSA-N 0.000 claims description 4
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical group FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 claims description 4
- 150000008280 chlorinated hydrocarbons Chemical group 0.000 claims description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- 238000007717 redox polymerization reaction Methods 0.000 claims 1
- 238000006116 polymerization reaction Methods 0.000 description 29
- -1 bromine compound Chemical class 0.000 description 20
- 229920001577 copolymer Polymers 0.000 description 19
- 238000004073 vulcanization Methods 0.000 description 16
- 239000000203 mixture Substances 0.000 description 14
- 238000010060 peroxide vulcanization Methods 0.000 description 12
- 229920000642 polymer Polymers 0.000 description 12
- 229920001897 terpolymer Polymers 0.000 description 11
- 230000000052 comparative effect Effects 0.000 description 10
- 150000001451 organic peroxides Chemical class 0.000 description 9
- ZYNPYKGTNSXKPI-UHFFFAOYSA-N 1-bromo-1,1,2,2-tetrafluoro-2-iodoethane Chemical compound FC(F)(Br)C(F)(F)I ZYNPYKGTNSXKPI-UHFFFAOYSA-N 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- BQCIDUSAKPWEOX-UHFFFAOYSA-N 1,1-Difluoroethene Chemical compound FC(F)=C BQCIDUSAKPWEOX-UHFFFAOYSA-N 0.000 description 7
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- 239000007789 gas Substances 0.000 description 7
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 7
- 239000000178 monomer Substances 0.000 description 6
- 239000005060 rubber Substances 0.000 description 6
- 238000004132 cross linking Methods 0.000 description 5
- 239000008367 deionised water Substances 0.000 description 5
- 229910021641 deionized water Inorganic materials 0.000 description 5
- 125000002573 ethenylidene group Chemical group [*]=C=C([H])[H] 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 125000001246 bromo group Chemical group Br* 0.000 description 4
- 239000012986 chain transfer agent Substances 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 150000002497 iodine compounds Chemical class 0.000 description 4
- 230000006855 networking Effects 0.000 description 4
- 230000000704 physical effect Effects 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- BLTXWCKMNMYXEA-UHFFFAOYSA-N 1,1,2-trifluoro-2-(trifluoromethoxy)ethene Chemical compound FC(F)=C(F)OC(F)(F)F BLTXWCKMNMYXEA-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 3
- 150000001993 dienes Chemical class 0.000 description 3
- HCDGVLDPFQMKDK-UHFFFAOYSA-N hexafluoropropylene Chemical compound FC(F)=C(F)C(F)(F)F HCDGVLDPFQMKDK-UHFFFAOYSA-N 0.000 description 3
- 150000002430 hydrocarbons Chemical group 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 238000007789 sealing Methods 0.000 description 3
- KHXKESCWFMPTFT-UHFFFAOYSA-N 1,1,1,2,2,3,3-heptafluoro-3-(1,2,2-trifluoroethenoxy)propane Chemical compound FC(F)=C(F)OC(F)(F)C(F)(F)C(F)(F)F KHXKESCWFMPTFT-UHFFFAOYSA-N 0.000 description 2
- ZTBODMIILURWSD-UHFFFAOYSA-N 1-(2-bromoethyl)-4-(2-iodoethyl)benzene Chemical compound BrCCC1=CC=C(CCI)C=C1 ZTBODMIILURWSD-UHFFFAOYSA-N 0.000 description 2
- 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 2
- LEJBBGNFPAFPKQ-UHFFFAOYSA-N 2-(2-prop-2-enoyloxyethoxy)ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOC(=O)C=C LEJBBGNFPAFPKQ-UHFFFAOYSA-N 0.000 description 2
- IVIVPNPSOKZKJQ-UHFFFAOYSA-N 2-bromo-1-chloro-1-iodoethane Chemical compound ClC(I)CBr IVIVPNPSOKZKJQ-UHFFFAOYSA-N 0.000 description 2
- KUDUQBURMYMBIJ-UHFFFAOYSA-N 2-prop-2-enoyloxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC(=O)C=C KUDUQBURMYMBIJ-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium peroxydisulfate Substances [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 2
- VAZSKTXWXKYQJF-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)OOS([O-])=O VAZSKTXWXKYQJF-UHFFFAOYSA-N 0.000 description 2
- 229910001870 ammonium persulfate Inorganic materials 0.000 description 2
- 150000001491 aromatic compounds Chemical class 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
- 239000006229 carbon black Substances 0.000 description 2
- 239000003638 chemical reducing agent Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000003431 cross linking reagent Substances 0.000 description 2
- HQWPLXHWEZZGKY-UHFFFAOYSA-N diethylzinc Chemical compound CC[Zn]CC HQWPLXHWEZZGKY-UHFFFAOYSA-N 0.000 description 2
- 229910001873 dinitrogen Inorganic materials 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 238000007720 emulsion polymerization reaction Methods 0.000 description 2
- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 description 2
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 150000002902 organometallic compounds Chemical class 0.000 description 2
- 229920000768 polyamine Polymers 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 238000010557 suspension polymerization reaction Methods 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- LALRXNPLTWZJIJ-UHFFFAOYSA-N triethylborane Chemical compound CCB(CC)CC LALRXNPLTWZJIJ-UHFFFAOYSA-N 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- OSXLRDYJNUYAQG-UHFFFAOYSA-N (1-bromo-1,2,2-trifluoro-2-iodoethyl)benzene Chemical compound FC(F)(I)C(F)(Br)C1=CC=CC=C1 OSXLRDYJNUYAQG-UHFFFAOYSA-N 0.000 description 1
- WRXCBRHBHGNNQA-UHFFFAOYSA-N (2,4-dichlorobenzoyl) 2,4-dichlorobenzenecarboperoxoate Chemical compound ClC1=CC(Cl)=CC=C1C(=O)OOC(=O)C1=CC=C(Cl)C=C1Cl WRXCBRHBHGNNQA-UHFFFAOYSA-N 0.000 description 1
- WSRKYYKHNUTYFT-UHFFFAOYSA-N (2-bromo-1,2,2-trifluoro-1-iodoethyl)benzene Chemical compound FC(F)(Br)C(F)(I)C1=CC=CC=C1 WSRKYYKHNUTYFT-UHFFFAOYSA-N 0.000 description 1
- 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
- GWTYBAOENKSFAY-UHFFFAOYSA-N 1,1,1,2,2-pentafluoro-2-(1,2,2-trifluoroethenoxy)ethane Chemical compound FC(F)=C(F)OC(F)(F)C(F)(F)F GWTYBAOENKSFAY-UHFFFAOYSA-N 0.000 description 1
- BOSAWIQFTJIYIS-UHFFFAOYSA-N 1,1,1-trichloro-2,2,2-trifluoroethane Chemical compound FC(F)(F)C(Cl)(Cl)Cl BOSAWIQFTJIYIS-UHFFFAOYSA-N 0.000 description 1
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
- RKIMETXDACNTIE-UHFFFAOYSA-N 1,1,2,2,3,3,4,4,5,5,6,6-dodecafluorocyclohexane Chemical compound FC1(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C1(F)F RKIMETXDACNTIE-UHFFFAOYSA-N 0.000 description 1
- RBTROQHBNLSUTL-UHFFFAOYSA-N 1,1,2,2,3,4-hexafluoro-3,4-bis(trifluoromethyl)cyclobutane Chemical compound FC(F)(F)C1(F)C(F)(F)C(F)(F)C1(F)C(F)(F)F RBTROQHBNLSUTL-UHFFFAOYSA-N 0.000 description 1
- UGCSPKPEHQEOSR-UHFFFAOYSA-N 1,1,2,2-tetrachloro-1,2-difluoroethane Chemical compound FC(Cl)(Cl)C(F)(Cl)Cl UGCSPKPEHQEOSR-UHFFFAOYSA-N 0.000 description 1
- AEGUVNHLYAZFAU-UHFFFAOYSA-N 1,1,2,3,3,4,4,5,5,6,6,7,8,8-tetradecafluoroocta-1,7-diene Chemical compound FC(F)=C(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)=C(F)F AEGUVNHLYAZFAU-UHFFFAOYSA-N 0.000 description 1
- KJXCOHSPZKKOBK-UHFFFAOYSA-N 1,1,2,3,3,4,5,5-octafluoropenta-1,4-diene Chemical compound FC(F)=C(F)C(F)(F)C(F)=C(F)F KJXCOHSPZKKOBK-UHFFFAOYSA-N 0.000 description 1
- FRCZRYZUJVSGKJ-UHFFFAOYSA-N 1,1,2,3,3-pentafluoropenta-1,4-diene Chemical compound FC(F)=C(F)C(F)(F)C=C FRCZRYZUJVSGKJ-UHFFFAOYSA-N 0.000 description 1
- NDMMKOCNFSTXRU-UHFFFAOYSA-N 1,1,2,3,3-pentafluoroprop-1-ene Chemical compound FC(F)C(F)=C(F)F NDMMKOCNFSTXRU-UHFFFAOYSA-N 0.000 description 1
- LGPPATCNSOSOQH-UHFFFAOYSA-N 1,1,2,3,4,4-hexafluorobuta-1,3-diene Chemical compound FC(F)=C(F)C(F)=C(F)F LGPPATCNSOSOQH-UHFFFAOYSA-N 0.000 description 1
- AJDIZQLSFPQPEY-UHFFFAOYSA-N 1,1,2-Trichlorotrifluoroethane Chemical compound FC(F)(Cl)C(F)(Cl)Cl AJDIZQLSFPQPEY-UHFFFAOYSA-N 0.000 description 1
- 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 1
- FWTUDISDSYABRU-UHFFFAOYSA-N 1,1,2-trifluorobuta-1,3-diene Chemical compound FC(F)=C(F)C=C FWTUDISDSYABRU-UHFFFAOYSA-N 0.000 description 1
- MIZLGWKEZAPEFJ-UHFFFAOYSA-N 1,1,2-trifluoroethene Chemical group FC=C(F)F MIZLGWKEZAPEFJ-UHFFFAOYSA-N 0.000 description 1
- QWSXJTYKCBAUTM-UHFFFAOYSA-N 1,1,2-trifluoropenta-1,4-diene Chemical compound FC(F)=C(F)CC=C QWSXJTYKCBAUTM-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
- MHDBWTRDEVNJDK-UHFFFAOYSA-N 1,1-dibromo-1,2,2-trifluoro-2-iodoethane Chemical compound FC(F)(I)C(F)(Br)Br MHDBWTRDEVNJDK-UHFFFAOYSA-N 0.000 description 1
- BAMUEXIPKSRTBS-UHFFFAOYSA-N 1,1-dichloro-1,2,2,2-tetrafluoroethane Chemical compound FC(F)(F)C(F)(Cl)Cl BAMUEXIPKSRTBS-UHFFFAOYSA-N 0.000 description 1
- XHGMOUXCWNPJHF-UHFFFAOYSA-N 1,1-difluoroethene;1,1,2,3,3,3-hexafluoroprop-1-ene;1,1,2,2-tetrafluoroethene Chemical group FC(F)=C.FC(F)=C(F)F.FC(F)=C(F)C(F)(F)F XHGMOUXCWNPJHF-UHFFFAOYSA-N 0.000 description 1
- SUTQSIHGGHVXFK-UHFFFAOYSA-N 1,2,2-trifluoroethenylbenzene Chemical compound FC(F)=C(F)C1=CC=CC=C1 SUTQSIHGGHVXFK-UHFFFAOYSA-N 0.000 description 1
- QVHWOZCZUNPZPW-UHFFFAOYSA-N 1,2,3,3,4,4-hexafluorocyclobutene Chemical compound FC1=C(F)C(F)(F)C1(F)F QVHWOZCZUNPZPW-UHFFFAOYSA-N 0.000 description 1
- GZQZKLFXWPAMFW-UHFFFAOYSA-N 1,2,3,4,5-pentafluoro-6-(1,2,2-trifluoroethenyl)benzene Chemical compound FC(F)=C(F)C1=C(F)C(F)=C(F)C(F)=C1F GZQZKLFXWPAMFW-UHFFFAOYSA-N 0.000 description 1
- YUBJHLYGOOZDRN-UHFFFAOYSA-N 1,2-dibromo-1,1,2-trifluoro-2-iodoethane Chemical compound FC(F)(Br)C(F)(Br)I YUBJHLYGOOZDRN-UHFFFAOYSA-N 0.000 description 1
- GQALTFRDRVDZAA-UHFFFAOYSA-N 1,2-dibromo-1,1,3,3,3-pentafluoro-2-iodopropane Chemical compound FC(F)(F)C(Br)(I)C(F)(F)Br GQALTFRDRVDZAA-UHFFFAOYSA-N 0.000 description 1
- DDMOUSALMHHKOS-UHFFFAOYSA-N 1,2-dichloro-1,1,2,2-tetrafluoroethane Chemical compound FC(F)(Cl)C(F)(F)Cl DDMOUSALMHHKOS-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
- AGCYCCSWNZZDCU-UHFFFAOYSA-N 1,3-bis(2-bromoethyl)-5-(2-iodoethyl)benzene Chemical compound BrCCC1=CC(CCBr)=CC(CCI)=C1 AGCYCCSWNZZDCU-UHFFFAOYSA-N 0.000 description 1
- HXYLVCDOWOUDAK-UHFFFAOYSA-N 1,3-bis(3-bromopropyl)-5-(2-iodoethyl)benzene Chemical compound BrCCCC1=CC(CCI)=CC(CCCBr)=C1 HXYLVCDOWOUDAK-UHFFFAOYSA-N 0.000 description 1
- XJSBXWPCISSOBG-UHFFFAOYSA-N 1,3-bis(3-bromopropyl)-5-(3-iodopropyl)benzene Chemical compound BrCCCC1=CC(CCCBr)=CC(CCCI)=C1 XJSBXWPCISSOBG-UHFFFAOYSA-N 0.000 description 1
- HWPARQYJJSWATJ-UHFFFAOYSA-N 1,3-dibromo-1,1,2,2,3,4,4-heptafluoro-4-iodobutane Chemical compound FC(F)(Br)C(F)(F)C(F)(Br)C(F)(F)I HWPARQYJJSWATJ-UHFFFAOYSA-N 0.000 description 1
- VSKRZGAHPADTKN-UHFFFAOYSA-N 1,3-dibromo-1,1,2,3,3-pentafluoro-2-iodopropane Chemical compound FC(F)(Br)C(F)(I)C(F)(F)Br VSKRZGAHPADTKN-UHFFFAOYSA-N 0.000 description 1
- MBNNVKRXNPVGOV-UHFFFAOYSA-N 1,3-dibromo-2,4,6-trifluoro-5-iodobenzene Chemical group FC1=C(Br)C(F)=C(I)C(F)=C1Br MBNNVKRXNPVGOV-UHFFFAOYSA-N 0.000 description 1
- NDAPWCGKOQXUMO-UHFFFAOYSA-N 1,3-dibromo-5-(2-iodoethyl)benzene Chemical compound BrC1=CC(Br)=CC(CCI)=C1 NDAPWCGKOQXUMO-UHFFFAOYSA-N 0.000 description 1
- CLAWBDDASOAHCP-UHFFFAOYSA-N 1,3-dibromo-5-(3-iodopropyl)benzene Chemical compound BrC1=CC(Br)=CC(CCCI)=C1 CLAWBDDASOAHCP-UHFFFAOYSA-N 0.000 description 1
- KARUMYWDGQTPFL-UHFFFAOYSA-N 1,3-dibromo-5-iodobenzene Chemical compound BrC1=CC(Br)=CC(I)=C1 KARUMYWDGQTPFL-UHFFFAOYSA-N 0.000 description 1
- GWQOYRSARAWVTC-UHFFFAOYSA-N 1,4-bis(2-tert-butylperoxypropan-2-yl)benzene Chemical compound CC(C)(C)OOC(C)(C)C1=CC=C(C(C)(C)OOC(C)(C)C)C=C1 GWQOYRSARAWVTC-UHFFFAOYSA-N 0.000 description 1
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- DLDJOUCIGKCPJB-UHFFFAOYSA-N 1,4-dibromo-1,1,2,2-tetrafluoro-3-iodobutane Chemical compound FC(F)(Br)C(F)(F)C(I)CBr DLDJOUCIGKCPJB-UHFFFAOYSA-N 0.000 description 1
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- 235000010265 sodium sulphite Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 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
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- DHCDFWKWKRSZHF-UHFFFAOYSA-L thiosulfate(2-) Chemical compound [O-]S([S-])(=O)=O DHCDFWKWKRSZHF-UHFFFAOYSA-L 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-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
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F214/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen
- C08F214/18—Monomers containing fluorine
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Paints Or Removers (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Processes Of Treating Macromolecular Substances (AREA)
- Polymerisation Methods In General (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62140420A JPS63304009A (ja) | 1987-06-04 | 1987-06-04 | 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 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE3818349A1 DE3818349A1 (de) | 1988-12-22 |
| DE3818349C2 true DE3818349C2 (de) | 1996-03-28 |
Family
ID=15268296
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE3818349A Expired - Lifetime DE3818349C2 (de) | 1987-06-04 | 1988-05-30 | Verfahren zur Herstellung von mittels Peroxid vulkanisierbaren, Fluor enthaltenden Elastomeren |
Country Status (3)
Families Citing this family (106)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH02245046A (ja) * | 1989-03-17 | 1990-09-28 | Nok Corp | ゴム組成物 |
| US5077359A (en) * | 1989-10-26 | 1991-12-31 | E. I. Du Pont De Nemours And Company | Peroxide-curable fluoroelastomers and chlorofluoroelastomers having bromine and iodine curesites and the preparation |
| 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 |
| FR2676067B1 (fr) * | 1991-05-02 | 1993-07-23 | Atochem | Composition a base de 1,1,1,3,3-pentafluorobutane et de methanol, pour le nettoyage et/ou le sechage de surfaces solides. |
| FR2676066B1 (fr) * | 1991-05-02 | 1993-07-23 | Atochem | Composition a base de 1,1-dichloro-1-fluoroethane, de 1,1,1,3,3-pentafluorobutane et de methanol, pour le nettoyage et/ou le sechage de surfaces solides. |
| 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 |
| WO1993023469A1 (en) * | 1992-05-11 | 1993-11-25 | Asahi Kasei Kogyo Kabushiki Kaisha | Fluoroelastomer composition and molding produced therefrom |
| IT1264125B1 (it) * | 1993-03-30 | 1996-09-16 | Ausimont Spa | Fluoroelastomeri dotati di elevata resistenza ai solventi polari ed alle basi |
| IT1265461B1 (it) * | 1993-12-29 | 1996-11-22 | Ausimont Spa | Fluoroelastomeri comprendenti unita' monomeriche derivanti da una bis-olefina |
| IT1273608B (it) * | 1995-04-28 | 1997-07-08 | Ausimont Spa | Fluoroelastomeri sostanzialmente privi di terminali polari e relativo processo di preparazione |
| IT1276979B1 (it) * | 1995-10-20 | 1997-11-03 | Ausimont Spa | Composizioni fluoroelastomeriche |
| IT1276980B1 (it) * | 1995-10-20 | 1997-11-03 | Ausimont Spa | Composizioni fluoroelastomeriche |
| DE19542501A1 (de) * | 1995-11-15 | 1997-05-22 | Bayer Ag | Peroxidisch vernetzbare Fluorkautschuke, ein Verfahren zu deren Herstellung und deren Verwendung |
| US5898054A (en) * | 1996-11-29 | 1999-04-27 | Nippon Mektron, Limited | Process for producing fluorine-containing elastomer |
| JP3758323B2 (ja) * | 1997-07-18 | 2006-03-22 | ユニマテック株式会社 | 含フッ素エラストマーの製造法 |
| IT1301780B1 (it) | 1998-06-23 | 2000-07-07 | Ausimont Spa | Fluoroelastomeri vulcanizzabili per via perossidica |
| IT1308628B1 (it) * | 1999-02-23 | 2002-01-09 | Ausimont Spa | Composizioni fluoroelastomeriche. |
| IT1308627B1 (it) | 1999-02-23 | 2002-01-09 | Ausimont Spa | Composizioni fluoroelastomeriche. |
| US7534845B2 (en) | 2000-04-21 | 2009-05-19 | Solvay Solexis S.P.A. | Fluorovinyl ethers and polymers obtainable therefrom |
| IT1318488B1 (it) * | 2000-04-21 | 2003-08-25 | Ausimont Spa | Fluorovinileteri e polimeri da essi ottenibili. |
| IT1318487B1 (it) * | 2000-04-21 | 2003-08-25 | Ausimont Spa | Fluoroelastomeri. |
| JP2002037818A (ja) * | 2000-05-18 | 2002-02-06 | Nippon Mektron Ltd | 含フッ素共重合体とその製造方法 |
| IT1318594B1 (it) | 2000-06-23 | 2003-08-27 | Ausimont Spa | Processo di polimerizzazione di monomeri solfonici. |
| IT1318593B1 (it) | 2000-06-23 | 2003-08-27 | Ausimont Spa | Ionomeri fluorurati. |
| ITMI20010383A1 (it) * | 2001-02-26 | 2002-08-26 | Ausimont Spa | Membrane idrofiliche porose |
| ITMI20010384A1 (it) * | 2001-02-26 | 2002-08-26 | Ausimont Spa | Membrane idrofiliche porose |
| ITMI20011061A1 (it) * | 2001-05-22 | 2002-11-22 | Ausimont Spa | Composizioni fluoroelastomeriche |
| ITMI20011062A1 (it) * | 2001-05-22 | 2002-11-22 | Ausimont Spa | Composizioni fluoroelastomeriche |
| ITMI20011059A1 (it) * | 2001-05-22 | 2002-11-22 | Ausimont Spa | Composizioni fluoroelastomeriche |
| ITMI20011060A1 (it) * | 2001-05-22 | 2002-11-22 | Ausimont Spa | Composizioni fluoroelastomeriche |
| ITMI20011745A1 (it) * | 2001-08-09 | 2003-02-09 | Ausimont Spa | Processo per impregnare supporti |
| ITMI20012165A1 (it) | 2001-10-18 | 2003-04-18 | Ausimont Spa | Perfluoroelastomeri |
| ITMI20012164A1 (it) * | 2001-10-18 | 2003-04-18 | Ausimont Spa | Fluoroelastomeri |
| ITMI20012744A1 (it) | 2001-12-21 | 2003-06-21 | Ausimont Spa | Processo di polimerizzazione di monomeri solfonici |
| EP1537154A1 (en) * | 2002-09-12 | 2005-06-08 | 3M Innovative Properties Company | Fluoroelastomers with improved permeation resistance and method for making the same |
| JP4610856B2 (ja) | 2003-02-06 | 2011-01-12 | Ｎｏｋ株式会社 | フッ素ゴム系シール材用組成物及びフッ素ゴム系シール材 |
| EP1733232A1 (en) * | 2004-03-23 | 2006-12-20 | Quidel Corporation | Hybrid phase lateral flow assay |
| ITMI20040789A1 (it) * | 2004-04-22 | 2004-07-22 | Solvay Solexis Spa | Membrane fluorurate |
| ITMI20041251A1 (it) * | 2004-06-22 | 2004-09-22 | Solvay Solexis Spa | Gel di perfluoroelastomeri |
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| ITMI20041571A1 (it) * | 2004-07-30 | 2004-10-30 | Solvay Solexis Spa | Perfluoroelastomeri |
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| ITMI20052509A1 (it) * | 2005-12-28 | 2007-06-29 | Solvay Solexis Spa | Assemblati per dispositivi elettrochimici |
| US8242210B2 (en) | 2007-08-29 | 2012-08-14 | Solvay Solexis S.P.A. | (Per)fluoroelastomeric compositions |
| CN101835810B (zh) * | 2007-09-14 | 2013-04-03 | 3M创新有限公司 | 含碘的超低粘度无定形含氟聚合物 |
| WO2009065895A1 (en) * | 2007-11-22 | 2009-05-28 | Solvay Solexis S.P.A. | Vulcanisable fluoroelastomeric compositions |
| EP2065441A1 (en) | 2007-11-30 | 2009-06-03 | Solvay Solexis S.p.A. | Fluoroelastomer composition |
| US8263708B2 (en) * | 2008-12-05 | 2012-09-11 | Solvay Solexis S.P.A. | Vulcanized (per) fluoroelastomer sealing articles |
| EP2194094A1 (en) | 2008-12-08 | 2010-06-09 | Solvay Solexis S.p.A. | (Per)fluoroelastomer composition |
| TWI496796B (zh) | 2009-02-13 | 2015-08-21 | Solvay Solexis Spa | 全氟彈性體 |
| TWI482784B (zh) | 2009-02-13 | 2015-05-01 | Solvay Solexis Spa | 全氟彈性體 |
| US9359480B2 (en) | 2009-04-06 | 2016-06-07 | Entegris, Inc. | Non-dewetting porous membranes |
| CN102471427B (zh) | 2009-07-16 | 2014-12-10 | 大金工业株式会社 | 含氟嵌段共聚物的制造方法 |
| CN102770468B (zh) | 2009-12-18 | 2016-08-10 | 索尔维特殊聚合物意大利有限公司 | 用于生产氟弹性体的方法 |
| WO2012007374A1 (en) | 2010-07-14 | 2012-01-19 | Solvay Solexis S.P.A. | Fluoroelastomer composition |
| TWI523900B (zh) | 2010-07-20 | 2016-03-01 | 首威索勒希斯股份有限公司 | 氟彈性體組合物 |
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| EP2655441B1 (en) | 2010-12-20 | 2015-11-18 | Solvay Specialty Polymers Italy S.p.A. | Low viscosity fluoroelastomers |
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| KR20170084290A (ko) | 2014-11-20 | 2017-07-19 | 솔베이 스페셜티 폴리머스 이태리 에스.피.에이. | 다층 엘라스토머 물품 및 이의 제조 방법 |
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| JP2018522113A (ja) * | 2015-07-13 | 2018-08-09 | スリーエム イノベイティブ プロパティズ カンパニー | ヨウ素末端基を有するフッ素化熱硬化性プラスチック |
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| CN108603001B (zh) | 2015-12-14 | 2021-03-12 | 索尔维特殊聚合物意大利有限公司 | 氟弹性体组合物 |
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| US20200291147A1 (en) | 2016-03-11 | 2020-09-17 | Solvay Specialty Polymers Italy S.P.A. | Polyunsaturated compound for curing fluoroelastomer compositions |
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| EP3484953B1 (en) | 2016-07-18 | 2020-04-15 | Solvay Specialty Polymers Italy S.p.A. | Fluoroelastomer composition |
| JP2019524497A (ja) | 2016-07-26 | 2019-09-05 | ソルベイ スペシャルティ ポリマーズ イタリー エス．ピー．エー． | 燃料ホース |
| WO2018019754A1 (en) | 2016-07-28 | 2018-02-01 | Solvay Specialty Polymers Italy S.P.A. | Electric circuit including a flexible conductor |
| KR102387250B1 (ko) | 2016-10-27 | 2022-04-19 | 솔베이 스페셜티 폴리머스 이태리 에스.피.에이. | 플루오로엘라스토머 조성물 |
| US11208540B2 (en) * | 2017-03-31 | 2021-12-28 | Solvay Specialty Polymers Italy S.P.A. | Method of making cured parts |
| EP3601427B1 (en) * | 2017-03-31 | 2023-05-10 | Solvay Specialty Polymers Italy S.p.A. | Fluoroelastomer composition |
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| CN111801383A (zh) | 2018-02-12 | 2020-10-20 | 索尔维特殊聚合物意大利有限公司 | 氟弹性体可固化的组合物 |
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| CN110760026B (zh) * | 2018-07-26 | 2021-06-22 | 中昊晨光化工研究院有限公司 | 一种四丙氟橡胶的合成方法及其四丙氟橡胶 |
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| US20220017736A1 (en) | 2018-12-19 | 2022-01-20 | Solvay Specialty Polymers Italy S.P.A. | Curable composition |
| WO2021099336A1 (en) | 2019-11-22 | 2021-05-27 | Solvay Specialty Polymers Italy S.P.A. | Method for improving coefficient of friction in cured fluororubber parts |
| WO2021123114A1 (en) | 2019-12-18 | 2021-06-24 | Solvay Specialty Polymers Italy S.P.A. | Base-resistant fluoroelastomer composition |
| EP4173727A4 (en) * | 2020-06-25 | 2024-05-29 | Agc Inc. | Paint and method for producing paint, and painted article and method for producing painted article |
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| US20250059308A1 (en) | 2021-12-17 | 2025-02-20 | Solvay Specialty Polymers Italy S.P.A. | Method for the emulsion polymerization of fluoromonomer |
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| WO2024115069A1 (en) | 2022-11-30 | 2024-06-06 | Solvay Specialty Polymers Italy S.P.A. | Method for manufacturing fluoroelastomers in aqueous emulsion without using fluorinated surfactants |
| WO2024120805A1 (en) | 2022-12-05 | 2024-06-13 | Solvay Specialty Polymers Italy S.P.A. | Composition (c) for manufacturing aqueous dispersion comprising particles of a fluorinated polymer (f) |
| WO2024165313A1 (en) | 2023-02-06 | 2024-08-15 | Solvay Specialty Polymers Italy S.P.A. | Method for manufacturing fluoroelastomers |
| WO2024200225A1 (en) | 2023-03-27 | 2024-10-03 | Solvay Specialty Polymers Italy S.P.A. | Curable fluoroelastomer composition |
| CN118725177A (zh) * | 2023-03-30 | 2024-10-01 | 大金工业株式会社 | 含氟弹性体的制造方法和含氟弹性体 |
| EP4556496A1 (en) | 2024-12-02 | 2025-05-21 | SOLVAY SPECIALTY POLYMERS ITALY S.p.A. | Method for manufacturing fluoroelastomers |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4035565A (en) * | 1975-03-27 | 1977-07-12 | E. I. Du Pont De Nemours And Company | Fluoropolymer containing a small amount of bromine-containing olefin units |
| JPS53125491A (en) * | 1977-04-08 | 1978-11-01 | Daikin Ind Ltd | Fluorine-containing polymer easily curable and its curable composition |
| JPS5920310A (ja) * | 1982-07-27 | 1984-02-02 | Daikin Ind Ltd | 含フッ素ポリマー硬化用組成物 |
| US4564662A (en) * | 1984-02-23 | 1986-01-14 | Minnesota Mining And Manufacturing Company | Fluorocarbon elastomer |
| CA1248286A (en) * | 1984-08-09 | 1989-01-03 | Paul G. Bekiarian | Improved fluoropolymer |
| US4748223A (en) * | 1986-04-01 | 1988-05-31 | Nippon Mektron Limited | Process for producing peroxide-vulcanizable, fluorine-containing elastomer |
-
1987
- 1987-06-04 JP JP62140420A patent/JPS63304009A/ja active Granted
-
1988
- 1988-05-17 US US07/194,941 patent/US4943622A/en not_active Expired - Lifetime
- 1988-05-30 DE DE3818349A patent/DE3818349C2/de not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPS63304009A (ja) | 1988-12-12 |
| JPH0157126B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1989-12-04 |
| US4943622A (en) | 1990-07-24 |
| DE3818349A1 (de) | 1988-12-22 |
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