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)
| Country | Link |
|---|---|
| US (1) | US4943622A (enExample) |
| JP (1) | JPS63304009A (enExample) |
| DE (1) | DE3818349C2 (enExample) |
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 |
| US5374484A (en) * | 1992-05-11 | 1994-12-20 | Asahi Kasei Kogyo Kabushiki Kaisha | Fluorine-containing elastomer composition and molded articles made 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 |
| DE69701251T2 (de) * | 1996-11-29 | 2000-06-21 | Nippon Mektron, Ltd. | Verfahren zur Herstellung eines Fluor-haltigen Elastomers |
| 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 |
| IT1308627B1 (it) * | 1999-02-23 | 2002-01-09 | Ausimont Spa | Composizioni fluoroelastomeriche. |
| IT1308628B1 (it) * | 1999-02-23 | 2002-01-09 | Ausimont Spa | Composizioni fluoroelastomeriche. |
| IT1318487B1 (it) * | 2000-04-21 | 2003-08-25 | Ausimont Spa | Fluoroelastomeri. |
| IT1318488B1 (it) * | 2000-04-21 | 2003-08-25 | Ausimont Spa | Fluorovinileteri e polimeri da essi ottenibili. |
| US7534845B2 (en) | 2000-04-21 | 2009-05-19 | Solvay Solexis S.P.A. | Fluorovinyl ethers and polymers obtainable therefrom |
| 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. |
| ITMI20010384A1 (it) * | 2001-02-26 | 2002-08-26 | Ausimont Spa | Membrane idrofiliche porose |
| ITMI20010383A1 (it) * | 2001-02-26 | 2002-08-26 | Ausimont Spa | Membrane idrofiliche porose |
| ITMI20011059A1 (it) * | 2001-05-22 | 2002-11-22 | Ausimont Spa | Composizioni fluoroelastomeriche |
| ITMI20011061A1 (it) * | 2001-05-22 | 2002-11-22 | Ausimont Spa | Composizioni fluoroelastomeriche |
| ITMI20011062A1 (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 |
| ITMI20012164A1 (it) * | 2001-10-18 | 2003-04-18 | Ausimont Spa | Fluoroelastomeri |
| ITMI20012165A1 (it) | 2001-10-18 | 2003-04-18 | Ausimont Spa | Perfluoroelastomeri |
| ITMI20012744A1 (it) | 2001-12-21 | 2003-06-21 | Ausimont Spa | Processo di polimerizzazione di monomeri solfonici |
| KR101022727B1 (ko) * | 2002-09-12 | 2011-03-22 | 쓰리엠 이노베이티브 프로퍼티즈 캄파니 | 내투과성이 향상된 플루오로엘라스토머 및 이의 제조 방법 |
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| JP2007530946A (ja) * | 2004-03-23 | 2007-11-01 | クイデル コーポレイション | ハイブリッド相ラテラルフロー・アッセイ |
| 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 |
| ITMI20041573A1 (it) * | 2004-07-30 | 2006-01-31 | Solvay Solexis Spa | Fluoroelastomeri |
| ITMI20052508A1 (it) | 2005-12-28 | 2007-06-29 | Solvay Solexis Spa | Processo per ottenere ccm con subgasket |
| ITMI20052509A1 (it) * | 2005-12-28 | 2007-06-29 | Solvay Solexis Spa | Assemblati per dispositivi elettrochimici |
| WO2009027213A1 (en) | 2007-08-29 | 2009-03-05 | 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 |
| ATE541894T1 (de) * | 2007-11-22 | 2012-02-15 | Solvay Solexis Spa | Vulkanisierbare fluorelastomerzusammensetzungen |
| EP2065441A1 (en) * | 2007-11-30 | 2009-06-03 | Solvay Solexis S.p.A. | Fluoroelastomer composition |
| JP5524233B2 (ja) * | 2008-12-05 | 2014-06-18 | ソルヴェイ・スペシャルティ・ポリマーズ・イタリー・エッセ・ピ・ア | 加硫（パー）フルオロエラストマーシール物品 |
| EP2194094A1 (en) | 2008-12-08 | 2010-06-09 | Solvay Solexis S.p.A. | (Per)fluoroelastomer composition |
| TWI482784B (zh) | 2009-02-13 | 2015-05-01 | Solvay Solexis Spa | 全氟彈性體 |
| TWI496796B (zh) | 2009-02-13 | 2015-08-21 | Solvay Solexis Spa | 全氟彈性體 |
| SG10201405601YA (en) | 2009-04-06 | 2014-10-30 | Entegris Inc | Non-dewetting porous membranes |
| US9127111B2 (en) | 2009-07-16 | 2015-09-08 | Daikin Industries, Ltd. | Process for production of fluorine-containing block copolymer |
| EP2513172B1 (en) | 2009-12-18 | 2014-02-26 | Solvay Specialty Polymers Italy S.p.A. | Method for manufacturing fluoroelastomers |
| 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 |
| JP5940549B2 (ja) | 2010-10-15 | 2016-06-29 | 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． | フルオロエラストマー |
| WO2012084587A1 (en) | 2010-12-20 | 2012-06-28 | Solvay Specialty Polymers Italy S.P.A. | Low viscosity fluoroelastomers |
| WO2012150253A1 (en) | 2011-05-03 | 2012-11-08 | Solvay Specialty Polymers Italy S.P.A. | Method for manufacturing fluoroelastomers |
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| CN103874716B (zh) | 2011-08-17 | 2017-04-05 | 索尔维特殊聚合物意大利有限公司 | 研磨方法 |
| US20160369021A1 (en) | 2013-06-28 | 2016-12-22 | Solvay Specialty Polymers Italy S.P.A. | Fluoroelastomers |
| US10377843B2 (en) | 2014-05-12 | 2019-08-13 | Solvay Specialty Polymers Italy S.P.A. | Method for the controlled polymerization of fluoromonomers |
| EP3172252B1 (en) | 2014-07-22 | 2020-09-30 | Solvay Specialty Polymers Italy S.p.A. | Perfluoroelastomer composition |
| US10513593B2 (en) | 2014-10-31 | 2019-12-24 | Solvay Specialty Polymers Italy S.P.A. | Fluoroelastomer composition |
| US20170306496A1 (en) | 2014-11-20 | 2017-10-26 | Solvay Specialty Polymers Italy S.P.A. | Multi-layered elastomer article and method for making the same |
| US11220588B2 (en) | 2015-05-29 | 2022-01-11 | Solvay Specialty Polymers Italy S.P.A. | Fluoroelastomer composition |
| 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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| US10882935B2 (en) | 2015-12-14 | 2021-01-05 | Solvay Specialty Polymers Italy S.P.A. | Method of manufacturing fluoroelastomers |
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| KR20180125155A (ko) | 2016-03-11 | 2018-11-22 | 솔베이 스페셜티 폴리머스 이태리 에스.피.에이. | 플루오로엘라스토머 조성물의 경화를 위한 다중불포화 화합물 |
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| JP2019517622A (ja) | 2016-06-13 | 2019-06-24 | 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． | 硬化性フルオロエラストマー組成物 |
| EP3484953B1 (en) | 2016-07-18 | 2020-04-15 | Solvay Specialty Polymers Italy S.p.A. | Fluoroelastomer composition |
| US20190162333A1 (en) | 2016-07-26 | 2019-05-30 | Solvay Specialty Polymers Italy S.P.A. | Fuel hose |
| WO2018019754A1 (en) | 2016-07-28 | 2018-02-01 | Solvay Specialty Polymers Italy S.P.A. | Electric circuit including a flexible conductor |
| JP7210440B2 (ja) | 2016-10-27 | 2023-01-23 | 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． | フルオロエラストマー組成物 |
| EP3601426B1 (en) * | 2017-03-31 | 2023-05-24 | Solvay Specialty Polymers Italy S.p.A. | Method of making cured parts |
| KR102552336B1 (ko) * | 2017-03-31 | 2023-07-07 | 솔베이 스페셜티 폴리머스 이태리 에스.피.에이. | 플루오로엘라스토머 조성물 |
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| WO2018219790A1 (en) | 2017-05-30 | 2018-12-06 | Solvay Specialty Polymers Italy S.P.A. | Shielded cables |
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| WO2019137920A1 (en) | 2018-01-10 | 2019-07-18 | Solvay Specialty Polymers Italy S.P.A. | Fluoroelastomer curable composition |
| JP7345484B2 (ja) | 2018-02-09 | 2023-09-15 | 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． | フルオロエラストマー硬化性組成物 |
| 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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| WO2020127108A1 (en) | 2018-12-19 | 2020-06-25 | Solvay Specialty Polymers Italy S.P.A. | Curable composition |
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| JPWO2021261450A1 (enExample) * | 2020-06-25 | 2021-12-30 | ||
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| WO2023247225A1 (en) | 2022-06-23 | 2023-12-28 | Solvay Specialty Polymers Italy S.P.A. | Process for manufacturing aqueous dispersion comprising particles of a fluorinated polymer (f) |
| CN120677185A (zh) | 2022-11-30 | 2025-09-19 | 世索科特殊聚合物意大利有限公司 | 用于在水性乳液中在不使用氟化表面活性剂的情况下制造含氟弹性体的方法 |
| 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 |
|---|---|
| JPH0157126B2 (enExample) | 1989-12-04 |
| US4943622A (en) | 1990-07-24 |
| JPS63304009A (ja) | 1988-12-12 |
| DE3818349A1 (de) | 1988-12-22 |
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