JPH01110546A - Transparent elastomer composition - Google Patents
Transparent elastomer compositionInfo
- Publication number
- JPH01110546A JPH01110546A JP26685787A JP26685787A JPH01110546A JP H01110546 A JPH01110546 A JP H01110546A JP 26685787 A JP26685787 A JP 26685787A JP 26685787 A JP26685787 A JP 26685787A JP H01110546 A JPH01110546 A JP H01110546A
- Authority
- JP
- Japan
- Prior art keywords
- ethylene
- weight
- olefin
- parts
- polysiloxane
- 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.)
- Pending
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 26
- 229920001971 elastomer Polymers 0.000 title claims abstract description 17
- 239000000806 elastomer Substances 0.000 title claims abstract description 16
- -1 polysiloxane Polymers 0.000 claims abstract description 36
- 229920001296 polysiloxane Polymers 0.000 claims abstract description 23
- 229920001577 copolymer Polymers 0.000 claims abstract description 18
- 239000004711 α-olefin Substances 0.000 claims abstract description 16
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims abstract description 13
- 239000006087 Silane Coupling Agent Substances 0.000 claims abstract description 8
- 150000001451 organic peroxides Chemical class 0.000 claims abstract description 7
- 239000002245 particle Substances 0.000 claims abstract description 6
- 229910021485 fumed silica Inorganic materials 0.000 claims abstract description 5
- 229920000089 Cyclic olefin copolymer Polymers 0.000 claims description 7
- 239000005977 Ethylene Substances 0.000 abstract description 6
- 150000001993 dienes Chemical class 0.000 abstract description 6
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 abstract description 5
- 229910052801 chlorine Inorganic materials 0.000 abstract description 3
- 239000007822 coupling agent Substances 0.000 abstract description 2
- 239000011954 Ziegler–Natta catalyst Substances 0.000 abstract 1
- 229920000642 polymer Polymers 0.000 description 12
- 230000000704 physical effect Effects 0.000 description 11
- 150000001875 compounds Chemical class 0.000 description 10
- 238000006116 polymerization reaction Methods 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 8
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
- 150000003624 transition metals Chemical class 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- SCPYDCQAZCOKTP-UHFFFAOYSA-N silanol Chemical compound [SiH3]O SCPYDCQAZCOKTP-UHFFFAOYSA-N 0.000 description 4
- 239000000377 silicon dioxide Substances 0.000 description 4
- 229910052723 transition metal Inorganic materials 0.000 description 4
- UFEKKYNQUHJSEC-UHFFFAOYSA-N 2-(5-bicyclo[2.2.1]hept-2-enyl)ethyl-chloro-dimethylsilane Chemical compound C1C2C(CC[Si](C)(Cl)C)CC1C=C2 UFEKKYNQUHJSEC-UHFFFAOYSA-N 0.000 description 3
- XDLMVUHYZWKMMD-UHFFFAOYSA-N 3-trimethoxysilylpropyl 2-methylprop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C(C)=C XDLMVUHYZWKMMD-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000005340 laminated glass Substances 0.000 description 3
- 229910001629 magnesium chloride Inorganic materials 0.000 description 3
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 3
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 3
- 229910000077 silane Inorganic materials 0.000 description 3
- 229920002545 silicone oil Polymers 0.000 description 3
- WSSSPWUEQFSQQG-UHFFFAOYSA-N 4-methyl-1-pentene Chemical compound CC(C)CC=C WSSSPWUEQFSQQG-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 2
- 229910021551 Vanadium(III) chloride Inorganic materials 0.000 description 2
- 229910021552 Vanadium(IV) chloride Inorganic materials 0.000 description 2
- 125000005234 alkyl aluminium group Chemical group 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000007664 blowing Methods 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- IQYKECCCHDLEPX-UHFFFAOYSA-N chloro hypochlorite;magnesium Chemical compound [Mg].ClOCl IQYKECCCHDLEPX-UHFFFAOYSA-N 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- HQQADJVZYDDRJT-UHFFFAOYSA-N ethene;prop-1-ene Chemical group C=C.CC=C HQQADJVZYDDRJT-UHFFFAOYSA-N 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
- 125000002524 organometallic group Chemical group 0.000 description 2
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 2
- 239000004417 polycarbonate Substances 0.000 description 2
- 229920000515 polycarbonate Polymers 0.000 description 2
- 239000004926 polymethyl methacrylate Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000012744 reinforcing agent Substances 0.000 description 2
- 238000001226 reprecipitation Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 229910052719 titanium Inorganic materials 0.000 description 2
- 239000010936 titanium Substances 0.000 description 2
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 2
- YONPGGFAJWQGJC-UHFFFAOYSA-K titanium(iii) chloride Chemical compound Cl[Ti](Cl)Cl YONPGGFAJWQGJC-UHFFFAOYSA-K 0.000 description 2
- 229910052720 vanadium Inorganic materials 0.000 description 2
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 2
- JTJFQBNJBPPZRI-UHFFFAOYSA-J vanadium tetrachloride Chemical compound Cl[V](Cl)(Cl)Cl JTJFQBNJBPPZRI-UHFFFAOYSA-J 0.000 description 2
- HQYCOEXWFMFWLR-UHFFFAOYSA-K vanadium(iii) chloride Chemical compound [Cl-].[Cl-].[Cl-].[V+3] HQYCOEXWFMFWLR-UHFFFAOYSA-K 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- OJOWICOBYCXEKR-APPZFPTMSA-N (1S,4R)-5-ethylidenebicyclo[2.2.1]hept-2-ene Chemical compound CC=C1C[C@@H]2C[C@@H]1C=C2 OJOWICOBYCXEKR-APPZFPTMSA-N 0.000 description 1
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 1
- MFWFDRBPQDXFRC-LNTINUHCSA-N (z)-4-hydroxypent-3-en-2-one;vanadium Chemical compound [V].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O MFWFDRBPQDXFRC-LNTINUHCSA-N 0.000 description 1
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 1
- AFFLGGQVNFXPEV-UHFFFAOYSA-N 1-decene Chemical compound CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 1
- CRSBERNSMYQZNG-UHFFFAOYSA-N 1-dodecene Chemical compound CCCCCCCCCCC=C CRSBERNSMYQZNG-UHFFFAOYSA-N 0.000 description 1
- GQEZCXVZFLOKMC-UHFFFAOYSA-N 1-hexadecene Chemical compound CCCCCCCCCCCCCCC=C GQEZCXVZFLOKMC-UHFFFAOYSA-N 0.000 description 1
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 1
- MMNYUQOHNAGUBO-UHFFFAOYSA-N 1-tert-butylperoxyhex-1-yne Chemical compound CCCCC#COOC(C)(C)C MMNYUQOHNAGUBO-UHFFFAOYSA-N 0.000 description 1
- NOSXUFXBUISMPR-UHFFFAOYSA-N 1-tert-butylperoxyhexane Chemical compound CCCCCCOOC(C)(C)C NOSXUFXBUISMPR-UHFFFAOYSA-N 0.000 description 1
- HFDVRLIODXPAHB-UHFFFAOYSA-N 1-tetradecene Chemical compound CCCCCCCCCCCCC=C HFDVRLIODXPAHB-UHFFFAOYSA-N 0.000 description 1
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 1
- NOGVLXYGHGMTAQ-UHFFFAOYSA-N 2-(2-bicyclo[2.2.1]hept-5-enyl)butyl-chloro-dimethylsilane Chemical compound C12C=CC(C(C1)C(C[Si](Cl)(C)C)CC)C2 NOGVLXYGHGMTAQ-UHFFFAOYSA-N 0.000 description 1
- IQQQQAFEBIVWIY-UHFFFAOYSA-N 2-(2-bicyclo[2.2.1]hept-5-enyl)butyl-dichloro-methylsilane Chemical compound C12C=CC(C(C1)C(C[Si](Cl)(Cl)C)CC)C2 IQQQQAFEBIVWIY-UHFFFAOYSA-N 0.000 description 1
- CJDXXXGJGKORHQ-UHFFFAOYSA-N 2-(2-bicyclo[2.2.1]hept-5-enyl)propyl-chloro-dimethylsilane Chemical compound C12C=CC(C(C1)C(C[Si](Cl)(C)C)C)C2 CJDXXXGJGKORHQ-UHFFFAOYSA-N 0.000 description 1
- FRFKHKROYSRRFR-UHFFFAOYSA-N 2-(2-bicyclo[2.2.1]hept-5-enyl)propyl-dichloro-methylsilane Chemical compound C12C=CC(C(C1)C(C[Si](Cl)(Cl)C)C)C2 FRFKHKROYSRRFR-UHFFFAOYSA-N 0.000 description 1
- 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 1
- OJUABKSVDKOEHL-UHFFFAOYSA-N 2-(5-bicyclo[2.2.1]hept-2-enyl)ethyl-dichloro-methylsilane Chemical compound C1C2C(CC[Si](Cl)(Cl)C)CC1C=C2 OJUABKSVDKOEHL-UHFFFAOYSA-N 0.000 description 1
- RYPKRALMXUUNKS-UHFFFAOYSA-N 2-Hexene Natural products CCCC=CC RYPKRALMXUUNKS-UHFFFAOYSA-N 0.000 description 1
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 1
- YVSMQHYREUQGRX-UHFFFAOYSA-N 2-ethyloxaluminane Chemical compound CC[Al]1CCCCO1 YVSMQHYREUQGRX-UHFFFAOYSA-N 0.000 description 1
- CMAOLVNGLTWICC-UHFFFAOYSA-N 2-fluoro-5-methylbenzonitrile Chemical compound CC1=CC=C(F)C(C#N)=C1 CMAOLVNGLTWICC-UHFFFAOYSA-N 0.000 description 1
- LQIIEHBULBHJKX-UHFFFAOYSA-N 2-methylpropylalumane Chemical compound CC(C)C[AlH2] LQIIEHBULBHJKX-UHFFFAOYSA-N 0.000 description 1
- OXYZDRAJMHGSMW-UHFFFAOYSA-N 3-chloropropyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)CCCCl OXYZDRAJMHGSMW-UHFFFAOYSA-N 0.000 description 1
- YHQXBTXEYZIYOV-UHFFFAOYSA-N 3-methylbut-1-ene Chemical compound CC(C)C=C YHQXBTXEYZIYOV-UHFFFAOYSA-N 0.000 description 1
- SJECZPVISLOESU-UHFFFAOYSA-N 3-trimethoxysilylpropan-1-amine Chemical compound CO[Si](OC)(OC)CCCN SJECZPVISLOESU-UHFFFAOYSA-N 0.000 description 1
- UUEWCQRISZBELL-UHFFFAOYSA-N 3-trimethoxysilylpropane-1-thiol Chemical compound CO[Si](OC)(OC)CCCS UUEWCQRISZBELL-UHFFFAOYSA-N 0.000 description 1
- UGVVIPAIDGTTNN-UHFFFAOYSA-N C[Zr]C Chemical compound C[Zr]C UGVVIPAIDGTTNN-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 229920000181 Ethylene propylene rubber Polymers 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 1
- WGPDMSKUJGQDQG-UHFFFAOYSA-I [V+5].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O.CCCCCCCC([O-])=O.CCCCCCCC([O-])=O.CCCCCCCC([O-])=O Chemical compound [V+5].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O.CCCCCCCC([O-])=O.CCCCCCCC([O-])=O.CCCCCCCC([O-])=O WGPDMSKUJGQDQG-UHFFFAOYSA-I 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 238000005452 bending Methods 0.000 description 1
- SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 1
- IMYWWHFTFYFRAL-UHFFFAOYSA-N but-3-enyl-chloro-dimethylsilane Chemical compound C[Si](C)(Cl)CCC=C IMYWWHFTFYFRAL-UHFFFAOYSA-N 0.000 description 1
- QYDLCVNCOWIUET-UHFFFAOYSA-N but-3-enyl-dichloro-methylsilane Chemical compound C[Si](Cl)(Cl)CCC=C QYDLCVNCOWIUET-UHFFFAOYSA-N 0.000 description 1
- FPCJKVGGYOAWIZ-UHFFFAOYSA-N butan-1-ol;titanium Chemical compound [Ti].CCCCO.CCCCO.CCCCO.CCCCO FPCJKVGGYOAWIZ-UHFFFAOYSA-N 0.000 description 1
- GQVCNZBQZKXBMX-UHFFFAOYSA-N butan-2-one;toluene Chemical compound CCC(C)=O.CC1=CC=CC=C1 GQVCNZBQZKXBMX-UHFFFAOYSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- LKRBKNPREDAJJQ-UHFFFAOYSA-M chloro-di(propan-2-yl)alumane Chemical compound [Cl-].CC(C)[Al+]C(C)C LKRBKNPREDAJJQ-UHFFFAOYSA-M 0.000 description 1
- HLLCZAYJBZAXFU-UHFFFAOYSA-N chloro-dimethyl-oct-7-enylsilane Chemical compound C[Si](C)(Cl)CCCCCCC=C HLLCZAYJBZAXFU-UHFFFAOYSA-N 0.000 description 1
- KOHUASMRQIYLCF-UHFFFAOYSA-N chloro-dimethyl-pent-4-enylsilane Chemical compound C[Si](C)(Cl)CCCC=C KOHUASMRQIYLCF-UHFFFAOYSA-N 0.000 description 1
- ZFKBNMAYPWZKKK-UHFFFAOYSA-N chloro-hept-6-enyl-dimethylsilane Chemical compound C[Si](C)(Cl)CCCCCC=C ZFKBNMAYPWZKKK-UHFFFAOYSA-N 0.000 description 1
- NQKBNSIOLMRTDL-UHFFFAOYSA-N chloro-hex-5-enyl-dimethylsilane Chemical compound C[Si](C)(Cl)CCCCC=C NQKBNSIOLMRTDL-UHFFFAOYSA-N 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 230000015271 coagulation Effects 0.000 description 1
- 238000005345 coagulation Methods 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 238000007872 degassing Methods 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
- KTQYJQFGNYHXMB-UHFFFAOYSA-N dichloro(methyl)silicon Chemical compound C[Si](Cl)Cl KTQYJQFGNYHXMB-UHFFFAOYSA-N 0.000 description 1
- RHCGQKZOXUVLMR-UHFFFAOYSA-N dichloro-(5-methyl-1-bicyclo[2.2.1]hept-2-enyl)silane Chemical compound CC1C2C=CC(C1)(C2)[SiH](Cl)Cl RHCGQKZOXUVLMR-UHFFFAOYSA-N 0.000 description 1
- XQOLMPJRVURWFY-UHFFFAOYSA-N dichloro-hex-5-enyl-methylsilane Chemical compound C[Si](Cl)(Cl)CCCCC=C XQOLMPJRVURWFY-UHFFFAOYSA-N 0.000 description 1
- KUGFVFZVBCBQNO-UHFFFAOYSA-N dichloro-methyl-oct-7-enylsilane Chemical compound C[Si](Cl)(Cl)CCCCCCC=C KUGFVFZVBCBQNO-UHFFFAOYSA-N 0.000 description 1
- KSQLXUBJOGRPPS-UHFFFAOYSA-N dichloro-methyl-pent-4-enylsilane Chemical compound C[Si](Cl)(Cl)CCCC=C KSQLXUBJOGRPPS-UHFFFAOYSA-N 0.000 description 1
- HJXBDPDUCXORKZ-UHFFFAOYSA-N diethylalumane Chemical compound CC[AlH]CC HJXBDPDUCXORKZ-UHFFFAOYSA-N 0.000 description 1
- YNLAOSYQHBDIKW-UHFFFAOYSA-M diethylaluminium chloride Chemical compound CC[Al](Cl)CC YNLAOSYQHBDIKW-UHFFFAOYSA-M 0.000 description 1
- ZMXPNWBFRPIZFV-UHFFFAOYSA-M dipropylalumanylium;chloride Chemical compound [Cl-].CCC[Al+]CCC ZMXPNWBFRPIZFV-UHFFFAOYSA-M 0.000 description 1
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- RMTCVMQBBYEAPC-UHFFFAOYSA-K ethanolate;titanium(4+);trichloride Chemical compound [Cl-].[Cl-].[Cl-].CCO[Ti+3] RMTCVMQBBYEAPC-UHFFFAOYSA-K 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- GCPCLEKQVMKXJM-UHFFFAOYSA-N ethoxy(diethyl)alumane Chemical compound CCO[Al](CC)CC GCPCLEKQVMKXJM-UHFFFAOYSA-N 0.000 description 1
- MNFTYNIMQNJVJI-UHFFFAOYSA-N ethoxy(dipropyl)alumane Chemical compound CC[O-].CCC[Al+]CCC MNFTYNIMQNJVJI-UHFFFAOYSA-N 0.000 description 1
- UAIZDWNSWGTKFZ-UHFFFAOYSA-L ethylaluminum(2+);dichloride Chemical compound CC[Al](Cl)Cl UAIZDWNSWGTKFZ-UHFFFAOYSA-L 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- DPUXQWOMYBMHRN-UHFFFAOYSA-N hexa-2,3-diene Chemical compound CCC=C=CC DPUXQWOMYBMHRN-UHFFFAOYSA-N 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000011229 interlayer Substances 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910001510 metal chloride Inorganic materials 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N methyl ethyl ketone Substances CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 1
- CPOFMOWDMVWCLF-UHFFFAOYSA-N methyl(oxo)alumane Chemical compound C[Al]=O CPOFMOWDMVWCLF-UHFFFAOYSA-N 0.000 description 1
- NRQNMMBQPIGPTB-UHFFFAOYSA-N methylaluminum Chemical compound [CH3].[Al] NRQNMMBQPIGPTB-UHFFFAOYSA-N 0.000 description 1
- YSTQWZZQKCCBAY-UHFFFAOYSA-L methylaluminum(2+);dichloride Chemical compound C[Al](Cl)Cl YSTQWZZQKCCBAY-UHFFFAOYSA-L 0.000 description 1
- 239000005048 methyldichlorosilane Substances 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- CCCMONHAUSKTEQ-UHFFFAOYSA-N octadec-1-ene Chemical compound CCCCCCCCCCCCCCCCC=C CCCMONHAUSKTEQ-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000003014 reinforcing effect Effects 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 150000003609 titanium compounds Chemical class 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- SQBBHCOIQXKPHL-UHFFFAOYSA-N tributylalumane Chemical compound CCCC[Al](CCCC)CCCC SQBBHCOIQXKPHL-UHFFFAOYSA-N 0.000 description 1
- VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 description 1
- MCULRUJILOGHCJ-UHFFFAOYSA-N triisobutylaluminium Chemical compound CC(C)C[Al](CC(C)C)CC(C)C MCULRUJILOGHCJ-UHFFFAOYSA-N 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 1
- VSRBKQFNFZQRBM-UHFFFAOYSA-N tuaminoheptane Chemical compound CCCCCC(C)N VSRBKQFNFZQRBM-UHFFFAOYSA-N 0.000 description 1
- 229960003986 tuaminoheptane Drugs 0.000 description 1
- JBIQAPKSNFTACH-UHFFFAOYSA-K vanadium oxytrichloride Chemical compound Cl[V](Cl)(Cl)=O JBIQAPKSNFTACH-UHFFFAOYSA-K 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 238000004073 vulcanization Methods 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
- VPGLGRNSAYHXPY-UHFFFAOYSA-L zirconium(2+);dichloride Chemical compound Cl[Zr]Cl VPGLGRNSAYHXPY-UHFFFAOYSA-L 0.000 description 1
Landscapes
- Compositions Of Macromolecular Compounds (AREA)
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は透明エラストマー組成物に関し、さらに詳しく
は耐熱性に優れた透明なエチレン−α−オレフィン系エ
ラストマー組成物に関する。DETAILED DESCRIPTION OF THE INVENTION [Field of Industrial Application] The present invention relates to a transparent elastomer composition, and more particularly to a transparent ethylene-α-olefin elastomer composition having excellent heat resistance.
従来、ポリカーボネート、ポリメタクリル酸メチル、ポ
リ−4−メチルペンテン−1、エチレンプロピレン(ま
たはエチレンプロピレンジエン)共重合体(EP (D
)M) 、エチレンブテン−1(またはエチレンブテン
−1ジエン)共重合体(EB (D)M)などのエラス
トマーには、ある程度の光透過性が有ることが知られて
いる。ポリカーボネート、ポリメタクリル酸メチル、ポ
リ−4−メチルペンテン−1などは、プラスチックとし
てガラスの代替えに使用されているが、可撓性を満たす
ことができない。一方、EP (D)MおよびEB (
D)Mは、非架橋状態では機械的強度に劣り、また架橋
状態でも補強剤を添加しないと機械的強度を満足しない
。しかし、補強剤を添加すると不透明となってしまい、
透明性が要求される合わせガラスなどに用いることがで
きなかった。Conventionally, polycarbonate, polymethyl methacrylate, poly-4-methylpentene-1, ethylene propylene (or ethylene propylene diene) copolymer (EP (D
) M), ethylene butene-1 (or ethylene butene-1 diene) copolymer (EB (D)M) and other elastomers are known to have a certain degree of light transparency. Polycarbonate, polymethyl methacrylate, poly-4-methylpentene-1, and the like are used as plastics to replace glass, but they cannot satisfy the flexibility requirements. On the other hand, EP (D)M and EB (
D) M has poor mechanical strength in a non-crosslinked state, and even in a crosslinked state it does not satisfy the mechanical strength unless a reinforcing agent is added. However, when a reinforcing agent is added, it becomes opaque.
It could not be used in laminated glass that requires transparency.
本発明の目的は、前記従来技術の欠点を除去し、使用に
耐えうる機械的強度を保持した可撓性および耐熱性に優
れた透明エラストマー組成物を提供することにある。An object of the present invention is to provide a transparent elastomer composition that eliminates the drawbacks of the prior art and has excellent flexibility and heat resistance while maintaining mechanical strength that can withstand use.
本発明者らは、前記技術的課題を解決するため、鋭意研
究した結果、(a)分子中にポリシロキサン成分を含む
エチレン−α−オレフィン共重合体および/または分子
中にポリシロキサン成分を含むエチレン−α−オレフィ
ン−非共役ジエン共重合体、(bl平均粒径が25ミリ
ミクロン以下の煙霧質シリカ、(C)シランカップリン
グ剤、および(d)有機パーオキサイドを特定の割合で
配合することにより光学的に透明で優れた耐熱性を示す
エラストマー組成物が得られることを見出し、本発明に
到達した。In order to solve the above-mentioned technical problem, the present inventors conducted extensive research and found that (a) an ethylene-α-olefin copolymer containing a polysiloxane component in the molecule and/or an ethylene-α-olefin copolymer containing a polysiloxane component in the molecule; Ethylene-α-olefin-nonconjugated diene copolymer, (fumed silica with a BL average particle size of 25 millimicrons or less), (C) a silane coupling agent, and (d) an organic peroxide are blended in a specific ratio. The inventors have discovered that an elastomer composition that is optically transparent and exhibits excellent heat resistance can be obtained by this method, and the present invention has been achieved.
すなわち、本発明は、(a1分子中にポリシロキサン成
分を含むエチレン−α−オレフィン共重合体および/ま
たは分子中にポリシロキサン成分を含むエチレン−α−
オレフィン−非共役ジエン共重合体100重量部と、(
bl平均粒径が25ミリミクロン以下の煙霧質シリカ1
0〜80重量部と、(c)シランカップリング剤0.1
〜10重量部と、(dl有fiバーオキサイド1〜5重
量部とを含有することを特徴とする。That is, the present invention provides (an ethylene-α-olefin copolymer containing a polysiloxane component in the a1 molecule and/or an ethylene-α-olefin copolymer containing a polysiloxane component in the molecule)
100 parts by weight of an olefin-nonconjugated diene copolymer and (
Atomized silica 1 with an average particle size of 25 millimicrons or less
0 to 80 parts by weight, and (c) 0.1 silane coupling agent.
-10 parts by weight, and 1 to 5 parts by weight of (dl-fi peroxide).
本発明に用いられる(a1分子中にポリシロキサン成分
を含むエチレン−α−オレフィン共重合体および/また
は分子中にポリシロキサン成分を含むエチレン−α−オ
レフィン−非共役ジエン共重合体は、例えば次に示す2
つの方法で、遷移金属成分と有機全屈成分との組み合わ
せからなる公知のチグラーナソタ触媒を用いて重合する
ことにより得ることができる。The ethylene-α-olefin copolymer containing a polysiloxane component in the a1 molecule and/or the ethylene-α-olefin-nonconjugated diene copolymer containing a polysiloxane component in the molecule used in the present invention (a1) is, for example, 2 shown in
It can be obtained by polymerization using a known Zigrana Sota catalyst consisting of a combination of a transition metal component and an organic total component.
(1)エチレンと、α−オレフィン(またはα−オレフ
ィンと非共役ジエン)と、少なくとも1つの5i−X(
ただし、Xは塩素原子または臭素原子)結合をもつ不飽
和シラン化合物とを共重合して得られる共重合体に、水
酸基を有するポリシロキサンを反応させる方法。(1) Ethylene, an α-olefin (or an α-olefin and a non-conjugated diene), and at least one 5i-X (
(X is a chlorine atom or a bromine atom) A method in which a copolymer obtained by copolymerizing an unsaturated silane compound with a bond is reacted with a polysiloxane having a hydroxyl group.
(2)少なくとも1つの5i−X(ただし、Xは塩素原
子または臭素原子)結合をもつ不飽和シラン化合物と水
酸基を有するポリシロキサンを反応させて得られた反応
生成物と、エチレンと、α−オレフィン(またはα−オ
レフィンと非共役ジエン)とを共重合する方法。(2) A reaction product obtained by reacting an unsaturated silane compound having at least one 5i-X (where X is a chlorine or bromine atom) bond with a polysiloxane having a hydroxyl group, ethylene, and α- A method of copolymerizing olefins (or α-olefins and nonconjugated dienes).
前記α−オレフィンとしては、炭素数3〜2゜のα−オ
レフィンが用いられ、例えばプロピレン、ブテン−1、
ペンテン−1,3−メチルブテン−1、ヘキセン−1,
4−メチルペンテン−1,4゜4−ジメチルペンテン−
1、オクテン−1、ノネン−1、デセン−1、ウンデセ
ン−11ドデセン=1、テトラデセン−1、ヘキサデセ
ン−1、オクタデセン−1、エイコセン−1などが挙げ
られるが、これらのうらプロピレン−1およびブテン−
1が好ましい。As the α-olefin, an α-olefin having a carbon number of 3 to 2° is used, such as propylene, butene-1,
pentene-1,3-methylbutene-1, hexene-1,
4-Methylpentene-1,4゜4-dimethylpentene-
1, octene-1, nonene-1, decene-1, undecene-11, dodecene-1, tetradecene-1, hexadecene-1, octadecene-1, eicosene-1, etc. −
1 is preferred.
また非共役ジエンとしては、例えば5−エチリデン−2
−ノルボルネン、■、4−へキサジエン、ジシクロペン
タジェンなどを用いることができる。Further, as the non-conjugated diene, for example, 5-ethylidene-2
-Norbornene, (1), 4-hexadiene, dicyclopentadiene, etc. can be used.
前記少なくとも1つの5i−X結合をもつ不飽和シラン
化合物としては、例えば−数式■(式中、nは1〜3の
整数、mは0〜12の整数、R1は炭素e!i、1〜6
のアルキル基、R2およびR3は互いに同一もしくは異
なり水素原子および/または炭素数1〜6のアルキル基
を示す)で表されるシラン化合物および一数式■
CH2=CH−+CH2)工S i Xk R43−k
(II)(式中、kは1〜3の整数、lは2〜12
の整数、R4は炭素数1〜6のアルキル基を示す)で表
されるシラン化合物を例示することができる。The unsaturated silane compound having at least one 5i-X bond may be, for example, represented by the following formula: 6
, R2 and R3 are the same or different from each other and represent a hydrogen atom and/or an alkyl group having 1 to 6 carbon atoms) and a silane compound represented by the formula ■ CH2=CH-+CH2) Engineering S i Xk R43- k
(II) (wherein k is an integer of 1 to 3, l is 2 to 12
and R4 represents an alkyl group having 1 to 6 carbon atoms.
−数式■で表されるシラン化合物として、例えば5−メ
チルジクロルシリルノルボルネン、5−ジメチルクロル
シリルノルボルネン、2−(5−ノルボルネニル)エチ
ルメチルジクロルシラン、2−(5−ノルボルネニル)
エチルジメチルクロルシラン、2− (5−ノルボルネ
ニル)プロピルメチルジクロルシラン、2− (5−ノ
ルボルネニル)プロピルジメチルクロルシラン、2−
(5−ノルボルネニル)ブチルメチルジクロルシラン、
2−(5−ノルボルネニル)ブチルジメチルクロルシラ
ンなどが挙げられる。- As a silane compound represented by the formula (■), for example, 5-methyldichlorosilylnorbornene, 5-dimethylchlorosilylnorbornene, 2-(5-norbornenyl)ethylmethyldichlorosilane, 2-(5-norbornenyl)
Ethyldimethylchlorosilane, 2- (5-norbornenyl)propylmethyldichlorosilane, 2- (5-norbornenyl)propyldimethylchlorosilane, 2-
(5-norbornenyl)butylmethyldichlorosilane,
Examples include 2-(5-norbornenyl)butyldimethylchlorosilane.
また−数式■で表されるシラン化合物として、例えば(
3−ブテニル)ジメチルクロルシラン、(4−ペンテニ
ル)ジメチルクロルシラン、(5〜へキセニル)ジメチ
ルクロルシラン、(6−ヘプテニル)ジメチルクロルシ
ラン、(7−オクテニル)ジメチルクロルシラン、(3
−ブテニル)メチルジクロルシラン、(4−ペンテニル
)メチルジクロルシラン、(5−へキセニル)メチルジ
クロルシラン、(6−へブテニル)メチルジクロルシラ
ン、(7−オクテニル)メチルジクロルシランなどが挙
げられる。In addition, as a silane compound represented by the formula ■, for example (
3-butenyl)dimethylchlorosilane, (4-pentenyl)dimethylchlorosilane, (5-hexenyl)dimethylchlorosilane, (6-heptenyl)dimethylchlorosilane, (7-octenyl)dimethylchlorosilane, (3
-butenyl)methyldichlorosilane, (4-pentenyl)methyldichlorosilane, (5-hexenyl)methyldichlorosilane, (6-hebutenyl)methyldichlorosilane, (7-octenyl)methyldichlorosilane, etc. can be mentioned.
これらのシラン化合物は1種または2種以上併用して用
いることができる。These silane compounds can be used alone or in combination of two or more.
前記水酸基を有するポリシロキサンとしては、例えば一
般弐■
(ヱ(中、o、rはOまたは1の整数、p、qは1〜1
00,000の整数、Rジ、R6、R13、RI4は互
いに同一もしくは異なり水素原子および/または炭素数
1〜5のアルキル基、R?、R8、R9、R10、R1
1、R12は互いに同一もしくは異なり炭素数1〜6の
アルキル基、フェニル基またはビニル基を示す)で表さ
れる化合物が用いられる。As the polysiloxane having a hydroxyl group, for example, general 2
An integer of 00,000, Rdi, R6, R13, and RI4 are the same or different from each other and are a hydrogen atom and/or an alkyl group having 1 to 5 carbon atoms, R? , R8, R9, R10, R1
1 and R12 are the same or different and represent an alkyl group having 1 to 6 carbon atoms, a phenyl group, or a vinyl group.
一般弐■で表される化合物としては、市販の水酸基変性
シリコーンオイルが使用でき、例えばポリジフェニル、
シロキサン末端シラノール、ポリジメチルシロキサン末
端シラノール、ポリジメチルジフェニルシロキサン末端
シラノール、ポリジメチルメチルビニルシロキサン末端
シラノール、ポリジメチルポリシロキサン末端カルビノ
ールなどが挙げられる。As the compound represented by general 2, commercially available hydroxyl-modified silicone oils can be used, such as polydiphenyl,
Examples include siloxane-terminated silanol, polydimethylsiloxane-terminated silanol, polydimethyldiphenylsiloxane-terminated silanol, polydimethylmethylvinylsiloxane-terminated silanol, and polydimethylpolysiloxane-terminated carbinol.
前記遷移金属成分としては、例えばチタン、ジルコニウ
ム、バナジウム、クロム等の化合物、特に好ましくはチ
タン、バナジウムの化合物が用いられる。これらの遷移
金属成分は、MgCl2等の金属塩化物、シリカ、アル
ミナなどにより担持されたもの、また担持の際に電子供
与性化合物を使用したものなどを用いることもできる。As the transition metal component, for example, compounds such as titanium, zirconium, vanadium, and chromium are used, and compounds of titanium and vanadium are particularly preferably used. These transition metal components may be supported by metal chlorides such as MgCl2, silica, alumina, etc., or may be supported using electron-donating compounds.
例えば次の遷移金属成分が例示される。For example, the following transition metal components are exemplified.
(イ)三塩化チタン、四塩化チタンおよびその組成物(
例えばTiCff3 ・AlC13)(ロ)四塩化チタ
ン、三塩化エトキシチタン、三塩化チタン、テトラブト
キシチタン等のチタン化合物を各種担体に、場合により
有機酸エステル、水、アミン類、アミド類、エーテル類
、アルコール類等の電子供与性化合物とともに担持させ
た担持触媒成分
ここで担体とはシリカ、アルミナ、シリカ・アルミナ、
チタニア、マグネシア、塩化マグネシウムおよびその組
成物(例えば塩化マグネシウムとルイス酸とからなる組
成物等)、オキシ塩化マグネシウム、オキシ塩化マグネ
シウムとアルキルアルミニウムジクロリドとの反応生成
物などが挙げられる。(a) Titanium trichloride, titanium tetrachloride and their compositions (
For example, TiCff3 ・AlC13) (b) Titanium compounds such as titanium tetrachloride, ethoxytitanium trichloride, titanium trichloride, and tetrabutoxytitanium are used as carriers, and optionally organic acid esters, water, amines, amides, ethers, etc. A supported catalyst component supported together with an electron-donating compound such as an alcohol. Here, the support is silica, alumina, silica/alumina,
Examples include titania, magnesia, magnesium chloride and compositions thereof (for example, compositions consisting of magnesium chloride and a Lewis acid), magnesium oxychloride, and reaction products of magnesium oxychloride and alkyl aluminum dichloride.
(ハ)オキシ三塩化バナジウム、四塩化バナジウム、三
塩化バナジウム、バナジウムアセチルアセトナート、ハ
ナジールアセチルアセトナート、バナジウムオクタネー
トおよびその組成物(ニ)三塩化バナジウム、四塩化バ
ナジウムを各種担体に場合により有機酸エステル、水、
アミン類、アミド類、エーテル類、アルコール類等の電
子供与性化合物とともに担持させた担持触媒成分(ホ)
ビスシクロペンタジェニルジメチルジルコニウム、ビス
シクロペンタジェニルジルコニウムジクロライドおよび
その組成物
また有機金属成分としては、例えばアルミニウム、マグ
ネシウム、リチウム等の金属のアルキル化合物またはハ
ロアルキル化合物が用いられ、これらのうち特に有機ア
ルミニウム化合物が好ましい。(c) Vanadium oxytrichloride, vanadium tetrachloride, vanadium trichloride, vanadium acetylacetonate, hanadyl acetylacetonate, vanadium octanate and their compositions (d) Vanadium trichloride, vanadium tetrachloride optionally in various carriers. organic acid ester, water,
Supported catalyst component (e) supported together with electron-donating compounds such as amines, amides, ethers, alcohols, etc.
Biscyclopentagenyl dimethyl zirconium, biscyclopentagenyl zirconium dichloride and its compositions.As the organometallic component, for example, alkyl compounds or haloalkyl compounds of metals such as aluminum, magnesium, lithium, etc. are used, and among these, especially organic Aluminum compounds are preferred.
有機アルミニウム化合物としては、例えばトリメチルア
ルミニウム、トリエチルアルミニウム、トリイソブチル
アルミニウム、トリノルマルブチルアルミニウム等のト
リアルキルアルミニウム、ジエチルアルミニウムクロラ
イド、ジ−n−プロピルアルミニウムクロライド、ジイ
ソプロピルアルミニウムクロライド等のジアルキルアル
ミニウムクロライド、メチルアルミニウムセスキクロラ
イド、エチルアルミニウムセスキクロライド、n−プロ
ビルアルミニウムセスキクロライド、イソブチルアルミ
ニウムセスキクロライド等のアルキルアルミニウムセス
キクロライド、ジエチルアルミニウムヒドリド、ジイソ
ブチルアルミニウムヒドリド等のジアルキルアルミニウ
ムヒドリド、メチルアルミニウムジクロライド、エチル
アルミニウムジクロライド、イソプロピルアルミニウム
ジクロライド等のアルキルアルミニウムジクロライド、
ジエチルアルミニウムエトキシド、ジノルマルプロピル
アルミニウムエトキシド等のジアルキルアルミニウムア
ルコキシド、メチルアルミノキサン、エチルアルミノキ
サン等の環状有機アルミニウムなどが用いられる。これ
らの有機アルミニウム化合物は2種以上を併用すること
もでき、また電子供与性化合物と併用することもできる
。Examples of organoaluminum compounds include trialkylaluminum such as trimethylaluminum, triethylaluminum, triisobutylaluminum, tri-n-butylaluminum, dialkylaluminum chloride such as diethylaluminum chloride, di-n-propylaluminum chloride, diisopropylaluminum chloride, and methylaluminum. Sesquichloride, ethylaluminum sesquichloride, n-probylaluminum sesquichloride, alkylaluminum sesquichloride such as isobutylaluminum sesquichloride, dialkylaluminum hydride such as diethylaluminum hydride, diisobutylaluminum hydride, methylaluminum dichloride, ethylaluminum dichloride, isopropylaluminum Alkylaluminum dichloride such as dichloride,
Dialkyl aluminum alkoxides such as diethylaluminum ethoxide and di-n-propyl aluminum ethoxide, and cyclic organoaluminums such as methylaluminoxane and ethylaluminoxane are used. Two or more of these organoaluminum compounds can be used in combination, or they can also be used in combination with an electron-donating compound.
前記遷移全屈成分と有機金属成分の組成比には特に制約
がないが、通常遷移金属原子1モルに対してを0.1〜
5000モル、好ましくは0.5〜2000モル、特に
好ましくは1〜500モルの割合で用いられる。There is no particular restriction on the composition ratio of the transition total bending component and the organometallic component, but it is usually 0.1 to 1 mole of transition metal atom.
It is used in a proportion of 5000 mol, preferably 0.5 to 2000 mol, particularly preferably 1 to 500 mol.
本発明による共重合体の重合の条件は、重合温度が一8
0〜200℃、特に10〜150’c、重合圧力がO〜
150kg/cnl−G、特に0〜50kg/cd−G
、、重合時間が0.1〜3時間、特に0.2〜2時間が
好ましい。The conditions for polymerization of the copolymer according to the present invention are as follows:
0-200°C, especially 10-150'c, polymerization pressure O~
150kg/cnl-G, especially 0-50kg/cd-G
The polymerization time is preferably 0.1 to 3 hours, particularly 0.2 to 2 hours.
重合方法としては特に制限はなく、n−へキサン、n−
へブタン、n−オクタン等の不活性溶媒を用いる溶液正
合法、実質的に溶媒を加えず七ツマー自身が溶媒の役割
を果たすスラリ重合法などが用いられる。また共重合の
分子量調節剤として水素および/またはアルキル亜鉛化
合物を用いることもできる。There are no particular restrictions on the polymerization method, and n-hexane, n-
A solution polymerization method using an inert solvent such as hebutane or n-octane, a slurry polymerization method in which the heptamine itself acts as a solvent without adding any solvent, and the like are used. Further, hydrogen and/or an alkylzinc compound can also be used as a molecular weight regulator for copolymerization.
本発明における分子中にポリシロキサン成分を含むエチ
レン−α−オレフィン共重合体および分子中にポリシロ
キサン成分を含むエチレン−α−オレフィン−非共役ジ
エン共重合体中のエチレンとα−オレフィンは、得られ
るエラストマー組成物の透明性の点から、重量比で17
3〜3の範囲が好ましい。非共役ジエンの含量は、特に
制約はない。ムーニー粘度(M L 1+4100℃)
は、加工性の点から5〜100が好ましい。またポリシ
ロキサンは、前記共重合体中に0.5〜20重量%の範
囲で含まれるのが好ましく、特に好ましくは1〜1oi
ut部の範囲である。ポリシロキサン含量が0.5[t
%未満では得られるエラストマー組成物の耐熱性が劣る
場合があり、また20重量%を超えると透明性が劣る場
合があり好ましくない。Ethylene and α-olefin in the ethylene-α-olefin copolymer containing a polysiloxane component in the molecule and the ethylene-α-olefin-nonconjugated diene copolymer containing a polysiloxane component in the molecule in the present invention are From the viewpoint of transparency of the elastomer composition, the weight ratio is 17.
The range of 3 to 3 is preferable. The content of non-conjugated diene is not particularly limited. Mooney viscosity (M L 1+4100℃)
is preferably 5 to 100 from the viewpoint of workability. Further, polysiloxane is preferably contained in the copolymer in an amount of 0.5 to 20% by weight, particularly preferably 1 to 1 oi
This is the range of the ut section. Polysiloxane content is 0.5 [t
If it is less than 20% by weight, the resulting elastomer composition may have poor heat resistance, and if it exceeds 20% by weight, transparency may be poor, which is not preferred.
本発明に用いられる(′b)平均粒径が25ミリミクロ
ン以下の煙霧質シリカとしては、例えばカポシルMS−
7、カポシルS−17(キャボソト(Cabot)社製
)、R−972(デグッサ(Degussa)社製)な
どが挙げられる。平均粒径が25ミリミクロンを超える
と得られたニジストマー組成物の透明性が損なわれる。Examples of the fumed silica ('b) having an average particle size of 25 millimicrons or less used in the present invention include Kaposil MS-
7, Caposil S-17 (manufactured by Cabot), R-972 (manufactured by Degussa), and the like. When the average particle size exceeds 25 millimicrons, the transparency of the resulting nidistomer composition is impaired.
これらの使用量は、前記共重合体100重量部に対して
10〜80重量部である。使用量が10重量部未満では
十分な補強効果が得られずエラストマー組成物の機械的
強度が劣る。また80重量部を超えると過充基となり得
られたエラストマー組成物の機械的強度が劣る。The amount used is 10 to 80 parts by weight based on 100 parts by weight of the copolymer. If the amount used is less than 10 parts by weight, a sufficient reinforcing effect will not be obtained and the mechanical strength of the elastomer composition will be poor. Moreover, if it exceeds 80 parts by weight, the resulting elastomer composition becomes overfilled and has poor mechanical strength.
本発明に用いられる(C)シランカップリング剤として
は、メトキシ基、エトキシ基を持ったアルコキシシラン
カップリング剤が特に有効であり、例えばビ互ルトリエ
トキシシラン、γ−クロロプロピルトリメトキシシラン
、γ−クロロプロピルメチルジェトキシシラン、γ−ア
ミノプロピルトリエトキシシラン、N−(β−アミノエ
チル)〜γ−アミノプロピルトリメトキシシラン、N−
(β−アミノエチル)−r−アミノプロピルメチルジメ
トキシシラン、γ−メルカプトプロピルトリメトキシシ
ラン、γ−グリシドキシプロピルトリメトキシシラン、
T−グリシドキシプロビルメチルジメトキシシラン、γ
−メタクリロキシプロピルトリメトキシシラン、T−メ
タクリロキシプロピルメチルジメトキシシランなどが挙
げられる。これらのうちγ−メタクリロキシプロピルト
リメトキシシランが好ましい。As the silane coupling agent (C) used in the present invention, alkoxysilane coupling agents having a methoxy group or an ethoxy group are particularly effective, such as bi-altriethoxysilane, γ-chloropropyltrimethoxysilane, -chloropropylmethyljethoxysilane, γ-aminopropyltriethoxysilane, N-(β-aminoethyl) to γ-aminopropyltrimethoxysilane, N-
(β-aminoethyl)-r-aminopropylmethyldimethoxysilane, γ-mercaptopropyltrimethoxysilane, γ-glycidoxypropyltrimethoxysilane,
T-glycidoxypropylmethyldimethoxysilane, γ
-methacryloxypropyltrimethoxysilane, T-methacryloxypropylmethyldimethoxysilane, and the like. Among these, γ-methacryloxypropyltrimethoxysilane is preferred.
シランカップリング剤の使用量は、前記共重合体100
重量部に対して0.1〜10重量部である。The amount of silane coupling agent used is 100% of the above copolymer.
The amount is 0.1 to 10 parts by weight.
使用量が0.1重量部未満では十分な耐熱性向上効果が
得られず、また10重量部を超えると常態物性が悪くな
る。耐熱性向上の面から2重量部以上であることが好ま
しい。If the amount used is less than 0.1 parts by weight, a sufficient effect of improving heat resistance cannot be obtained, and if it exceeds 10 parts by weight, the normal physical properties will deteriorate. From the viewpoint of improving heat resistance, the amount is preferably 2 parts by weight or more.
本発明に用いられる(dl有機パーオキサイドとしては
、例えばジクミルパーオキサイド、1,1−ビス(む−
ブチルパーオキシ)3,3.5−トリメチルシクロヘキ
サン、2.5−ジメチル−2゜5−ジ(t−ブチルパー
オキシ)ヘキサン、2.゛5−ジメチルー2.5−ジ(
t−ブチルパーオキシ)ヘキシン、ジーt−プチルパオ
キサイドなどが挙げられる。The dl organic peroxide used in the present invention includes, for example, dicumyl peroxide, 1,1-bis(mu-
butylperoxy)3,3.5-trimethylcyclohexane, 2.5-dimethyl-2°5-di(t-butylperoxy)hexane, 2.゛5-dimethyl-2,5-di(
(t-butylperoxy)hexyne, di-t-butyl peroxide, and the like.
有機パーオキサイドの使用量は前記共重合体100重量
部に対して1〜5重量部である。使用量が1重量部未満
では、機械的強度が低下し、5重量部を超えると架橋密
度が高くなりすぎ、伸びが低下する。The amount of organic peroxide used is 1 to 5 parts by weight based on 100 parts by weight of the copolymer. If the amount used is less than 1 part by weight, mechanical strength will decrease, and if it exceeds 5 parts by weight, the crosslinking density will become too high and elongation will decrease.
本発明のエラストマー組成物の製造に際しては、その透
明性を損なわない範囲で、酸化防止剤、架橋助剤、軟化
剤を配合することが可能であり、通常のゴム用混練り機
、例えばバンバリーミキサ−、ニーダーブレンダー、イ
ンターミキサー、2本ロール機などを用いることができ
る。When producing the elastomer composition of the present invention, it is possible to blend an antioxidant, a crosslinking aid, and a softener within a range that does not impair its transparency. -, a kneader blender, an intermixer, a two-roll machine, etc. can be used.
本発明のエラストマーはその透明性を利用して、合わせ
ガラス内層に特に有用である。The elastomers of the present invention are particularly useful in laminated glass inner layers because of their transparency.
以下、本発明を実施例により詳細に説明する。 Hereinafter, the present invention will be explained in detail with reference to Examples.
なお、実施例中の部および%は特に断らない限り重量部
および重量%を表す。In addition, parts and % in the examples represent parts by weight and % by weight unless otherwise specified.
本実施例中の物性試験はJIS K6301に準じて
行ない、またヘイズの測定はスガ試験機社製5M−3型
(HGM−2に併用)により測定した。Physical property tests in this example were carried out in accordance with JIS K6301, and haze was measured using Suga Test Instruments Model 5M-3 (used in conjunction with HGM-2).
実施例I
A)分子中にポリシロキサン成分を含むエチレンプロピ
レン共重合体の合成
予め窒素置換した31セパラブルフラスコに脱水精製し
たn−ヘキサン21を仕込み、エチレン/プロピレン/
水素=515/2 (モル比)の混合ガスを20℃で
10分間予備溶解したのち、AllEtll誌Cl 1
.!s 5ミリモルを加えた。別に2−(5−ノルボル
ネニル)エチルジメチルクロルシラン2モルに対して両
末端水酸基変性シリコーンオイル(東芝シリコーン社製
、分子量2200)1モルを窒素雰囲気下25℃にて5
時間攪拌後、脱気して生成物Aを得た。この生成物A1
.25ミリモルおよびVOCN30.5ミリモルを前記
セパラブルフラスコに順次仕込み、20℃にて混合ガス
を吹き込みながら30分間重合させた。30分後反応溶
液にイソプロピルアルコール5mlを仕込み重合反応を
停止したのちメタノール凝固し、次いで生成ポリマーを
100℃の熱ロールにて乾燥した。生成ポリマーの収量
は31g、ムーニー粘度(M L 1+4100℃)は
45.0、プロピレン含量は35.0%、l・ルエンー
メチルエチルケトンによる再沈$i!製後のポリシロキ
サン含量は4.8%であった。Example I A) Synthesis of ethylene propylene copolymer containing a polysiloxane component in the molecule Dehydrated and purified n-hexane 21 was charged into a 31 separable flask that had been purged with nitrogen in advance, and ethylene/propylene/
After preliminarily melting a mixed gas of hydrogen = 515/2 (molar ratio) at 20°C for 10 minutes, AllEtll magazine Cl 1
.. ! s 5 mmol was added. Separately, 1 mol of silicone oil modified with hydroxyl groups at both ends (manufactured by Toshiba Silicone Co., Ltd., molecular weight 2200) was added to 2 mol of 2-(5-norbornenyl)ethyldimethylchlorosilane at 25°C under a nitrogen atmosphere for 50 minutes.
After stirring for an hour, product A was obtained by degassing. This product A1
.. 25 mmol and 30.5 mmol of VOCN were sequentially charged into the separable flask, and polymerized for 30 minutes at 20° C. while blowing mixed gas. After 30 minutes, 5 ml of isopropyl alcohol was added to the reaction solution to stop the polymerization reaction, followed by coagulation with methanol, and then the resulting polymer was dried with a heated roll at 100°C. The yield of the produced polymer was 31 g, the Mooney viscosity (M L 1+4100°C) was 45.0, the propylene content was 35.0%, and the reprecipitation with l.luene-methyl ethyl ketone was $i! The polysiloxane content after manufacture was 4.8%.
B)物性試験
得られた生成ポリマーを使用し、第1表に示す配合処方
によりロール機にて混練りしたのち、シーテイングし、
160℃で35分プレス加硫した。B) Physical property test Using the resulting polymer, kneading it in a roll machine according to the formulation shown in Table 1, then sheeting it,
Press vulcanization was performed at 160°C for 35 minutes.
得られた2龍厚シートについてヘイズおよび物性試験を
実施した。その結果を第2表に示すが、優れた透明性、
機械的強度および耐熱性を示した。Haze and physical property tests were conducted on the obtained 2 Dragon thick sheet. The results are shown in Table 2. Excellent transparency,
It showed mechanical strength and heat resistance.
比較例1
実施例1において、ポリマーとして日本合□成ゴム社製
のエチレンプロピレンゴムJSREPIIを用いた以外
は実施例1と同様にして物性を測定した。その結果を第
2表に示すが、透明性は優れているが、耐熱性に劣った
。Comparative Example 1 Physical properties were measured in the same manner as in Example 1 except that ethylene propylene rubber JSREP II manufactured by Nippon Gosei Rubber Co., Ltd. was used as the polymer. The results are shown in Table 2, and the transparency was excellent, but the heat resistance was poor.
第1表
町・・・煙霧質カーボン、キャポフト社製ネ2・・・シ
ランカップリング剤、日本ユニカー社製ネ3・・・有機
パーオキサイド、日本油脂社製実施例2
A)分子中にポリシロキサン成分を含むエチレンプロピ
レン共重合体の合成
予め窒素置換した31セパラブルフラスコに脱水精製し
たn−ヘキサン2Nを仕込み、エチレン/プロピレン/
水素=515/4 (モル比)の混合ガスを20℃で1
0分間溶解させたのち、AβBtu、ジCJ l、$
5ミリモルを加えた。次いで2−(5−ノルボルネニル
)エチルジメチルクロルシラン1.25ミリモルおよび
VOCg30.5ミリモルを順次仕込み、20℃にて混
合ガスを吹き込みながら30分間重合させた。30分反
応後、七ツマーパージをしながら両末端水酸基変性シリ
コーンオイル(東芝シリコーン社製、分子量2200)
1、25 ミリモルを仕込み、25°Cにて30分攪拌
したのち、2−エチルヘキシルアルコール5 m lを
仕込んで重合反応を停止した。次いでメタノール凝固し
、100℃熱ロールにて生成ポリマーを乾燥した。Table 1 Town: Fumigated carbon, manufactured by Capoft Co., Ltd. 2: Silane coupling agent, manufactured by Nippon Unicar Co., Ltd. 3: Organic peroxide, manufactured by Nippon Oil & Fats Co., Ltd. Example 2 A) Polymer in the molecule Synthesis of ethylene propylene copolymer containing siloxane component 2N dehydrated n-hexane was charged into a 31 separable flask which had been purged with nitrogen.
Hydrogen = 515/4 (molar ratio) mixed gas at 20℃
After 0 min of dissolution, AβBtu, diCJl, $
5 mmol was added. Next, 1.25 mmol of 2-(5-norbornenyl)ethyldimethylchlorosilane and 30.5 mmol of VOCg were sequentially charged, and polymerization was carried out at 20° C. for 30 minutes while blowing a mixed gas. After 30 minutes of reaction, add silicone oil modified with hydroxyl groups at both ends (manufactured by Toshiba Silicone Co., Ltd., molecular weight 2200) while purging.
After charging 1.25 mmol and stirring at 25°C for 30 minutes, 5 ml of 2-ethylhexyl alcohol was charged to stop the polymerization reaction. Next, methanol was coagulated, and the resulting polymer was dried with a 100° C. hot roll.
生成ポリマーの収量は89g、ムーニー粘度(M L
1+< 100℃)は51.0.プロピレン含量は42
.0%、トルエン−メチルエチルケトン再沈精製後のポ
リシロキサン含量は1.90%であった。The yield of the produced polymer was 89 g, and the Mooney viscosity (M L
1+<100℃) is 51.0. Propylene content is 42
.. The polysiloxane content after toluene-methyl ethyl ketone reprecipitation purification was 1.90%.
B)物性試験
得られたポリマーを用いて実施例IB)と同じ方法で物
性の評価をした。その結果を第2表に示すが、優れた透
明性、機械的強度および耐熱性を示した。B) Physical property test Using the obtained polymer, the physical properties were evaluated in the same manner as in Example IB). The results are shown in Table 2, and showed excellent transparency, mechanical strength and heat resistance.
実施例3
実施例1において、カポシルMS−7の量を70部に代
えた以外は実施例1と同じ方法でポリマーを合成し、そ
の組成物の物性を評価した。その結果を第2表に示すが
、優れた透明性、機械的強度および耐熱性を示した。Example 3 A polymer was synthesized in the same manner as in Example 1 except that the amount of Kaposyl MS-7 was changed to 70 parts, and the physical properties of the composition were evaluated. The results are shown in Table 2, and showed excellent transparency, mechanical strength and heat resistance.
実施例4
実施例1において、A−174の量を5部に代えた以外
は実施例1と同じ方法でポリマーを合成し、その組成物
の物性を評価した。その結果を第2表に示すが、優れた
透明性、機械的強度および耐熱性を示した。Example 4 A polymer was synthesized in the same manner as in Example 1 except that the amount of A-174 was changed to 5 parts, and the physical properties of the composition were evaluated. The results are shown in Table 2, and showed excellent transparency, mechanical strength and heat resistance.
比較例2
実施例1において、カポシルMS−7の量を120部に
代えた以外は実施例1と同じ方法でポリマーを合成し、
その組成物の物性を評価した。その結果を第2表に示す
が、透明性および耐熱性は優れているが、機械的強度お
よびロール巻付性に劣った。Comparative Example 2 A polymer was synthesized in the same manner as in Example 1 except that the amount of Kaposyl MS-7 was changed to 120 parts,
The physical properties of the composition were evaluated. The results are shown in Table 2, and the transparency and heat resistance were excellent, but the mechanical strength and rollability were poor.
比較例3
実施例1において、カポシルMS−7の量を5部に代え
た以外は実施例1と同じ方法でポリマーを合成し、その
組成物の物性を評価した。その結果を第2表に示すが、
透明性と耐熱性が優れるが、機械的強度が大幅に劣った
。Comparative Example 3 A polymer was synthesized in the same manner as in Example 1 except that the amount of Kaposyl MS-7 was changed to 5 parts, and the physical properties of the composition were evaluated. The results are shown in Table 2.
Although it had excellent transparency and heat resistance, its mechanical strength was significantly inferior.
本発明の透明エラストマー組成物によれば、透明であり
、耐熱性を持った柔軟なエラストマーシートを得ること
ができる。これらは合わせガラス中間層材、バイザー等
に有用である。According to the transparent elastomer composition of the present invention, a transparent, heat-resistant and flexible elastomer sheet can be obtained. These are useful for laminated glass interlayer materials, visors, etc.
代理人 弁理士 川 北 武 長Agent: Patent Attorney Kawakita Takecho
Claims (1)
ン−α−オレフィン共重合体および/または分子中にポ
リシロキサン成分を含むエチレン−α−オレフィン−非
共役ジエン共重合体100重量部と、(b)平均粒径が
25ミリミクロン以下の煙霧質シリカ10〜80重量部
と、(c)シランカップリング剤0.1〜10重量部と
、(d)有機パーオキサイド1〜5重量部とを含有する
ことを特徴とする透明エラストマー組成物。(1) (a) 100 parts by weight of an ethylene-α-olefin copolymer containing a polysiloxane component in the molecule and/or an ethylene-α-olefin-nonconjugated diene copolymer containing a polysiloxane component in the molecule; (b) 10 to 80 parts by weight of fumed silica having an average particle size of 25 mm or less; (c) 0.1 to 10 parts by weight of a silane coupling agent; and (d) 1 to 5 parts by weight of organic peroxide. A transparent elastomer composition comprising:
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP26685787A JPH01110546A (en) | 1987-10-22 | 1987-10-22 | Transparent elastomer composition |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP26685787A JPH01110546A (en) | 1987-10-22 | 1987-10-22 | Transparent elastomer composition |
Publications (1)
Publication Number | Publication Date |
---|---|
JPH01110546A true JPH01110546A (en) | 1989-04-27 |
Family
ID=17436625
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP26685787A Pending JPH01110546A (en) | 1987-10-22 | 1987-10-22 | Transparent elastomer composition |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPH01110546A (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0388005A2 (en) * | 1989-02-24 | 1990-09-19 | Loctite Corporation | Selective monohydrosilation of vinyl and ethynyl functional norbornenes and curable products produced thereby |
CN112225852A (en) * | 2020-09-28 | 2021-01-15 | 浙江大学 | Polysiloxane functionalized ethylene-norbornene copolymer and preparation method thereof |
-
1987
- 1987-10-22 JP JP26685787A patent/JPH01110546A/en active Pending
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0388005A2 (en) * | 1989-02-24 | 1990-09-19 | Loctite Corporation | Selective monohydrosilation of vinyl and ethynyl functional norbornenes and curable products produced thereby |
JPH02248430A (en) * | 1989-02-24 | 1990-10-04 | Loctite Corp | Preparation of silicone having norbornene functional group and curable composition thereby obtained |
CN112225852A (en) * | 2020-09-28 | 2021-01-15 | 浙江大学 | Polysiloxane functionalized ethylene-norbornene copolymer and preparation method thereof |
CN112225852B (en) * | 2020-09-28 | 2021-10-08 | 浙江大学 | Polysiloxane functionalized ethylene-norbornene copolymer and preparation method thereof |
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