JP2015206058A - 高反応性イソブテンホモポリマー又はイソブテンコポリマーの製造方法 - Google Patents
高反応性イソブテンホモポリマー又はイソブテンコポリマーの製造方法 Download PDFInfo
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- JP2015206058A JP2015206058A JP2015163013A JP2015163013A JP2015206058A JP 2015206058 A JP2015206058 A JP 2015206058A JP 2015163013 A JP2015163013 A JP 2015163013A JP 2015163013 A JP2015163013 A JP 2015163013A JP 2015206058 A JP2015206058 A JP 2015206058A
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- Prior art keywords
- isobutene
- aluminum
- phenyl
- polymerization
- donor
- 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.)
- Granted
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- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 title claims abstract description 311
- 229920001577 copolymer Polymers 0.000 title claims abstract description 19
- 229920001519 homopolymer Polymers 0.000 title claims abstract description 18
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 11
- -1 aluminum alkylhalide Chemical class 0.000 claims abstract description 105
- 229910052782 aluminium Inorganic materials 0.000 claims abstract description 63
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims abstract description 61
- 229920002367 Polyisobutene Polymers 0.000 claims abstract description 54
- 239000000178 monomer Substances 0.000 claims abstract description 48
- 239000000203 mixture Substances 0.000 claims abstract description 42
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims abstract description 34
- 239000002685 polymerization catalyst Substances 0.000 claims abstract description 10
- 125000001033 ether group Chemical group 0.000 claims abstract description 4
- 150000002894 organic compounds Chemical class 0.000 claims abstract description 4
- 239000003999 initiator Substances 0.000 claims description 79
- 238000006116 polymerization reaction Methods 0.000 claims description 74
- 229920000642 polymer Polymers 0.000 claims description 38
- 238000000034 method Methods 0.000 claims description 33
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 30
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 21
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 20
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 16
- 150000001875 compounds Chemical class 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 12
- 150000002440 hydroxy compounds Chemical class 0.000 claims description 12
- 229910052799 carbon Inorganic materials 0.000 claims description 11
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 11
- BDCFWIDZNLCTMF-UHFFFAOYSA-N 2-phenylpropan-2-ol Chemical compound CC(C)(O)C1=CC=CC=C1 BDCFWIDZNLCTMF-UHFFFAOYSA-N 0.000 claims description 10
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 10
- 125000005843 halogen group Chemical group 0.000 claims description 9
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 9
- GTLWADFFABIGAE-UHFFFAOYSA-N 1-chloroethylbenzene Chemical compound CC(Cl)C1=CC=CC=C1 GTLWADFFABIGAE-UHFFFAOYSA-N 0.000 claims description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 8
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims description 8
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 8
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 8
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 7
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims description 6
- IUUULXXWNYKJSL-UHFFFAOYSA-N 4-methoxy-alpha-methylbenzyl alcohol Chemical compound COC1=CC=C(C(C)O)C=C1 IUUULXXWNYKJSL-UHFFFAOYSA-N 0.000 claims description 6
- 125000001931 aliphatic group Chemical group 0.000 claims description 6
- 150000001721 carbon Chemical group 0.000 claims description 6
- LEARFTRDZQQTDN-UHFFFAOYSA-N 2-[4-(2-hydroxypropan-2-yl)phenyl]propan-2-ol Chemical compound CC(C)(O)C1=CC=C(C(C)(C)O)C=C1 LEARFTRDZQQTDN-UHFFFAOYSA-N 0.000 claims description 5
- 238000007334 copolymerization reaction Methods 0.000 claims description 5
- WAPNOHKVXSQRPX-UHFFFAOYSA-N 1-phenylethanol Chemical compound CC(O)C1=CC=CC=C1 WAPNOHKVXSQRPX-UHFFFAOYSA-N 0.000 claims description 4
- 125000002723 alicyclic group Chemical group 0.000 claims description 4
- XPNGNIFUDRPBFJ-UHFFFAOYSA-N alpha-methylbenzylalcohol Natural products CC1=CC=CC=C1CO XPNGNIFUDRPBFJ-UHFFFAOYSA-N 0.000 claims description 4
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- 239000003701 inert diluent Substances 0.000 claims description 4
- 125000006736 (C6-C20) aryl group Chemical group 0.000 claims description 3
- KPJKMUJJFXZGAX-UHFFFAOYSA-N 2-chloropropan-2-ylbenzene Chemical compound CC(C)(Cl)C1=CC=CC=C1 KPJKMUJJFXZGAX-UHFFFAOYSA-N 0.000 claims description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 3
- 150000003222 pyridines Chemical class 0.000 claims description 3
- NBRKLOOSMBRFMH-UHFFFAOYSA-N tert-butyl chloride Chemical compound CC(C)(C)Cl NBRKLOOSMBRFMH-UHFFFAOYSA-N 0.000 claims description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 2
- 150000002148 esters Chemical group 0.000 claims description 2
- 150000002366 halogen compounds Chemical class 0.000 claims description 2
- 230000000379 polymerizing effect Effects 0.000 claims description 2
- 238000009826 distribution Methods 0.000 abstract description 5
- 150000007942 carboxylates Chemical group 0.000 abstract description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 162
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 80
- 238000006243 chemical reaction Methods 0.000 description 51
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 35
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 31
- 239000000243 solution Substances 0.000 description 27
- 239000002904 solvent Substances 0.000 description 18
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 16
- 239000003085 diluting agent Substances 0.000 description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 229930195733 hydrocarbon Natural products 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 10
- 239000004215 Carbon black (E152) Substances 0.000 description 9
- 125000004432 carbon atom Chemical group C* 0.000 description 9
- 150000002896 organic halogen compounds Chemical group 0.000 description 9
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 description 9
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 8
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 8
- 125000000524 functional group Chemical group 0.000 description 8
- 150000002431 hydrogen Chemical class 0.000 description 8
- 229920002554 vinyl polymer Polymers 0.000 description 8
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 7
- ITQTTZVARXURQS-UHFFFAOYSA-N beta-methylpyridine Natural products CC1=CC=CN=C1 ITQTTZVARXURQS-UHFFFAOYSA-N 0.000 description 7
- 239000003054 catalyst Substances 0.000 description 7
- 239000000460 chlorine Substances 0.000 description 7
- 229910052801 chlorine Inorganic materials 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 6
- BSKHPKMHTQYZBB-UHFFFAOYSA-N alpha-methylpyridine Natural products CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 6
- JVLSPCMZGXWITQ-UHFFFAOYSA-N cumene;2-phenylpropan-2-ol Chemical compound CC(C)C1=CC=CC=C1.CC(C)(O)C1=CC=CC=C1 JVLSPCMZGXWITQ-UHFFFAOYSA-N 0.000 description 6
- 125000004093 cyano group Chemical group *C#N 0.000 description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 6
- GBJYYVBFTCPLPK-UHFFFAOYSA-N C1(=CC=CC=C1)C(C)C.C1(=CC=CC=C1)CC(C)O Chemical compound C1(=CC=CC=C1)C(C)C.C1(=CC=CC=C1)CC(C)O GBJYYVBFTCPLPK-UHFFFAOYSA-N 0.000 description 5
- 229920001400 block copolymer Polymers 0.000 description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 5
- 150000008282 halocarbons Chemical class 0.000 description 5
- 150000002367 halogens Chemical group 0.000 description 5
- 125000005842 heteroatom Chemical group 0.000 description 5
- 150000002430 hydrocarbons Chemical class 0.000 description 5
- 238000011065 in-situ storage Methods 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- FKNQCJSGGFJEIZ-UHFFFAOYSA-N 4-methylpyridine Chemical compound CC1=CC=NC=C1 FKNQCJSGGFJEIZ-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- 229910015900 BF3 Inorganic materials 0.000 description 4
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 4
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 4
- 150000002170 ethers Chemical class 0.000 description 4
- 229910052731 fluorine Inorganic materials 0.000 description 4
- 239000011737 fluorine Substances 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 230000000977 initiatory effect Effects 0.000 description 4
- 239000002808 molecular sieve Substances 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 4
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-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
- 150000001298 alcohols Chemical class 0.000 description 3
- 150000001340 alkali metals Chemical class 0.000 description 3
- VTYYLEPIZMXCLO-UHFFFAOYSA-L calcium carbonate Substances [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 3
- 125000002091 cationic group Chemical group 0.000 description 3
- IAQRGUVFOMOMEM-ARJAWSKDSA-N cis-but-2-ene Chemical compound C\C=C/C IAQRGUVFOMOMEM-ARJAWSKDSA-N 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- 125000004185 ester group Chemical group 0.000 description 3
- 125000002573 ethenylidene group Chemical group [*]=C=C([H])[H] 0.000 description 3
- 235000019439 ethyl acetate Nutrition 0.000 description 3
- 229940052308 general anesthetics halogenated hydrocarbons Drugs 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 229920002521 macromolecule Polymers 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 3
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000004430 oxygen atom Chemical group O* 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 230000009257 reactivity Effects 0.000 description 3
- IAQRGUVFOMOMEM-ONEGZZNKSA-N trans-but-2-ene Chemical compound C\C=C\C IAQRGUVFOMOMEM-ONEGZZNKSA-N 0.000 description 3
- GETTZEONDQJALK-UHFFFAOYSA-N (trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC=C1 GETTZEONDQJALK-UHFFFAOYSA-N 0.000 description 2
- VFWCMGCRMGJXDK-UHFFFAOYSA-N 1-chlorobutane Chemical compound CCCCCl VFWCMGCRMGJXDK-UHFFFAOYSA-N 0.000 description 2
- BWZVCCNYKMEVEX-UHFFFAOYSA-N 2,4,6-Trimethylpyridine Chemical compound CC1=CC(C)=NC(C)=C1 BWZVCCNYKMEVEX-UHFFFAOYSA-N 0.000 description 2
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 2
- AUWDOZOUJWEPBA-UHFFFAOYSA-N 2-(4-methoxyphenyl)ethanol Chemical compound COC1=CC=C(CCO)C=C1 AUWDOZOUJWEPBA-UHFFFAOYSA-N 0.000 description 2
- FZXRXKLUIMKDEL-UHFFFAOYSA-N 2-Methylpropyl propanoate Chemical compound CCC(=O)OCC(C)C FZXRXKLUIMKDEL-UHFFFAOYSA-N 0.000 description 2
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 2
- SZNYYWIUQFZLLT-UHFFFAOYSA-N 2-methyl-1-(2-methylpropoxy)propane Chemical compound CC(C)COCC(C)C SZNYYWIUQFZLLT-UHFFFAOYSA-N 0.000 description 2
- WWUVJRULCWHUSA-UHFFFAOYSA-N 2-methyl-1-pentene Chemical compound CCCC(C)=C WWUVJRULCWHUSA-UHFFFAOYSA-N 0.000 description 2
- MHNNAWXXUZQSNM-UHFFFAOYSA-N 2-methylbut-1-ene Chemical compound CCC(C)=C MHNNAWXXUZQSNM-UHFFFAOYSA-N 0.000 description 2
- KDSNLYIMUZNERS-UHFFFAOYSA-N 2-methylpropanamine Chemical compound CC(C)CN KDSNLYIMUZNERS-UHFFFAOYSA-N 0.000 description 2
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 2
- VAJVDSVGBWFCLW-UHFFFAOYSA-N 3-Phenyl-1-propanol Chemical compound OCCCC1=CC=CC=C1 VAJVDSVGBWFCLW-UHFFFAOYSA-N 0.000 description 2
- JVZRCNQLWOELDU-UHFFFAOYSA-N 4-Phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=NC=C1 JVZRCNQLWOELDU-UHFFFAOYSA-N 0.000 description 2
- GDWRKZLROIFUML-UHFFFAOYSA-N 4-phenylbutan-2-ol Chemical compound CC(O)CCC1=CC=CC=C1 GDWRKZLROIFUML-UHFFFAOYSA-N 0.000 description 2
- PZASAAIJIFDWSB-CKPDSHCKSA-N 8-[(1S)-1-[8-(trifluoromethyl)-7-[4-(trifluoromethyl)cyclohexyl]oxynaphthalen-2-yl]ethyl]-8-azabicyclo[3.2.1]octane-3-carboxylic acid Chemical compound FC(F)(F)C=1C2=CC([C@@H](N3C4CCC3CC(C4)C(O)=O)C)=CC=C2C=CC=1OC1CCC(C(F)(F)F)CC1 PZASAAIJIFDWSB-CKPDSHCKSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical class ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 2
- FFOPEPMHKILNIT-UHFFFAOYSA-N Isopropyl butyrate Chemical compound CCCC(=O)OC(C)C FFOPEPMHKILNIT-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000003463 adsorbent Substances 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- VQGHOUODWALEFC-UHFFFAOYSA-N alpha-Phenylpyridine Natural products C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 2
- QVQLCTNNEUAWMS-UHFFFAOYSA-N barium oxide Chemical compound [Ba]=O QVQLCTNNEUAWMS-UHFFFAOYSA-N 0.000 description 2
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- OWUTVCVPEOXXHD-UHFFFAOYSA-N trimethoxy(prop-1-enyl)silane Chemical compound CO[Si](OC)(OC)C=CC OWUTVCVPEOXXHD-UHFFFAOYSA-N 0.000 description 1
- PZJJKWKADRNWSW-UHFFFAOYSA-N trimethoxysilicon Chemical group CO[Si](OC)OC PZJJKWKADRNWSW-UHFFFAOYSA-N 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- LZTRCELOJRDYMQ-UHFFFAOYSA-N triphenylmethanol Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(O)C1=CC=CC=C1 LZTRCELOJRDYMQ-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
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Abstract
【解決手段】ポリイソブテン鎖末端あたり末端ビニリデン二重結合含有量少なくとも50mol%及び多分散度好ましくは1.05から3.5未満を有する高反応性イソブテンホモポリマー又はイソブテンコポリマーの製造であって、イソブテン又はイソブテン含有モノマー混合物を、ドナーとして、少なくとも1のエーテル官能性又はカルボン酸エステル官能性を有する有機化合物を含有する、重合触媒として作用するアルミニウム三ハロゲン化物ドナー錯体又はアルミニウムアルキルハロゲン化物ドナー錯体、特にアルミニウム三塩化物ドナー錯体の存在下で重合させる製造。
【選択図】なし
Description
本発明は、ポリイソブテン鎖末端あたり末端ビニリデン二重結合含有量少なくとも50mol%を有する高反応性イソブテンホモポリマー又はイソブテンコポリマーの新規製造方法に関する。さらに、本発明は新規イソブテンポリマーに関する。
C1〜C8−アルキル基は、1〜8個の炭素原子を有する鎖状又は分枝状のアルキル基である。その例は、メチル、エチル、n−プロピル、イソプロピル、n−ブチル、2−ブチル、イソブチル、t−ブチル、ペンチル、1−メチルブチル、2−メチルブチル、3−メチルブチル、2,2−ジメチルプロピル、1−エチルプロピル、n−ヘキシル、1,1−ジメチルプロピル、1,2−ジメチルプロピル、1−メチルペンチル、2−メチルペンチル、3−メチルペンチル、4−メチルペンチル、1,1−ジメチルブチル、1,2−ジメチルブチル、1,3−ジメチルブチル、2,2−ジメチルブチル、2,3−ジメチルブチル、3,3−ジメチルブチル、1−エチルブチル、2−エチルブチル、1,1,2−トリメチルプロピル、1,2,2−トリメチルプロピル、1−エチル−1−メチルプロピル、1−エチル−2−メチルプロピル、n−ヘプチル、n−オクチル及びこれらの構造異性体、例えば2−エチルヘキシルである。この種のC1〜C8−アルキル基は、少ない程度で、ヘテロ原子、例えば酸素、窒素又はハロゲン原子、例えば塩素、及び/又は非プロトン性官能基、例えばカルボキシルエステル基、シアノ基又はニトロ基を含有することもできる。
R10、R11及びR12は、相互に独立して水素、C1〜C20−アルキル、C5〜C8−シクロアルキル、C6〜C20−アリール、C7〜C20−アルキルアリール又はフェニル、その際、芳香族核はさらに1又は複数のC1〜C4−アルキル基又はC1〜C4−アルコキシ基又は一般式II
その際、可変部R10、R11又はR12の最高で1つは水素を意味し、かつ、可変部R10、R11又はR12の少なくとも1はフェニルであり、これはさらに1又は複数のC1〜C4−アルキル基又はC1〜C4−アルコキシ基又は一般式IIの原子団を置換基として有することができる、かつ
nは9〜4500、好ましくは9〜180、特に9〜100、とりわけ12〜50の数である]
のイソブテンポリマーは、本発明の主題でもある。
純粋なイソブテン1.43g(25.5mmol)をジクロロメタン20ml及びn−ヘキサン5mlからの混合物中で−20℃で、三塩化アルミニウム及びジ−n−ブチルエーテル(モル比1:1)からの錯体(ジクロロメタン中の1モーラー溶液の形)0.62mmolを用いて30分間の間71%の変換率で、数平均モル質量Mn2095、多分散度(PDI)2.27及び末端ビニリデン二重結合含有量91モル%を有するポリイソブテンへと重合した。
純粋なイソブテン1.43g(25.5mmol)をジクロロメタン20ml及びn−ヘキサン5mlからの混合物中で−20℃で、三塩化アルミニウム及び酢酸エチルエステル(モル比1:1)からの錯体(ジクロロメタン中の1モーラー溶液の形)0.62mmolを用いて30分間の間17%の変換率で、数平均分子量Mn1930、多分散度(PDI)1.45及び末端ビニリデン二重結合含有量88mol%を有するポリイソブテンへと重合した。
純粋なイソブテン1.43g(25.5mmol)をジクロロメタン20ml及びn−ヘキサン5mlからの混合物中で−40℃で、三塩化アルミニウム及びジ−n−ブチルエーテル(モル比1:1)からの錯体(ジクロロメタン中の1モーラー溶液の形)0.62mmolを用いて、開始剤としての2−フェニル−2−プロパノール(クメン)0.5mmolの存在下で30分間の間62%の変換率で、数平均分子量Mn1515、多分散度(PDI)1.45及び末端ビニリデン二重結合含有量90mol%を有するポリイソブテンへと重合した。クメンにより開始したポリマー鎖の割合(leff)は70%であった。
純粋なイソブテン1.43g(25.5mmol)をジクロロメタン20ml及びn−ヘキサン5mlからの混合物中で−40℃で、三塩化アルミニウム及びジ−n−ブチルエーテル(モル比1:1)からの錯体(ジクロロメタン中の1モーラー溶液の形)1.24mmolを用いて、開始剤としての2−フェニル−2−プロパノール(クメン)1.0mmolの存在下で30分間の間76%の変換率で、数平均分子量Mn1180、多分散度(PDI)1.21及び末端ビニリデン二重結合含有量88mol%を有するポリイソブテンへと重合した。クメンにより開始したポリマー鎖の割合(leff)は90%であった。
純粋なイソブテン1.43g(25.5mmol)をジクロロメタン20ml及びn−ヘキサン5mlからの混合物中で−60℃で、三塩化アルミニウム及びジ−n−ブチルエーテル(モル比1:1)からの錯体(ジクロロメタン中の1モーラー溶液の形)0.62mmolを用いて、開始剤としての2−フェニル−2−プロパノール(クメン)0.5mmolの存在下で31分間の間91%の変換率で、数平均分子量Mn2275、多分散度(PDI)1.83及び末端ビニリデン二重結合含有量85mol%を有するポリイソブテンへと重合した。クメンにより開始したポリマー鎖の割合(leff)は90%であった。
純粋なイソブテン1.43g(25.5mmol)をジクロロメタン15ml及びn−ヘキサン10mlからの混合物中で−60℃で、三塩化アルミニウム及びジ−n−ブチルエーテル(モル比1:1)からの錯体(ジクロロメタン中の1モーラー溶液の形)0.36mmolを用いて、開始剤としての2−フェニル−2−プロパノール(クメン)0.29mmolの存在下で120分間の間56%の変換率で、数平均分子量Mn2690、多分散度(PDI)1.91及び末端ビニリデン二重結合含有量89mol%を有するポリイソブテンへと重合した。クメンにより開始したポリマー鎖の割合(leff)は88%であった。
純粋なイソブテン1.43g(25.5mmol)をジクロロメタン15ml及びn−ヘキサン10mlからの混合物中で−60℃で、三塩化アルミニウム及びジ−n−ブチルエーテル(モル比1:1)からの錯体(ジクロロメタン中の1モーラー溶液の形)0.36mmolを用いて、開始剤としての2−フェニル−2−プロパノール(クメン)0.09mmolの存在下で30分間の間47%の変換率で、数平均分子量Mn3510、多分散度(PDI)2.17及び末端ビニリデン二重結合含有量95mol%を有するポリイソブテンへと重合した。クメンにより開始したポリマー鎖の割合(leff)は37%であった。
実施例7aを繰り返し、その際、反応期間を4倍にした:120分後に、62%の変換率で、数平均分子量Mn3360、多分散度(PDI)1.93及び末端ビニリデン二重結合含有量91mol%を有するポリイソブテンが得られた。クメンにより開始したポリマー鎖の割合(leff)は23%であった。
純粋なイソブテン2.97g(53.0mmol)をジクロロメタン66ml中で−15℃で、三塩化アルミニウム及びジ−n−ブチルエーテル(モル比1:1)からの錯体(ジクロロメタン中の1モーラー溶液の形)2.15mmolを用いて、開始剤としての2−フェニル−2−プロパノール(クメン)1.0mmolの存在下で60分間の間40%の変換率で、数平均分子量Mn1675、多分散度(PDI)1.75及び末端ビニリデン二重結合含有量96mol%を有するポリイソブテンへと重合した。
純粋なイソブテン3.09g(55.0mmol)をジクロロメタン66ml中で−60℃で、三塩化アルミニウム及びジ−n−ブチルエーテル(モル比1:1)からの錯体(ジクロロメタン中の1モーラー溶液の形)1.80mmolを用いて、開始剤としての2−フェニル−2−プロパノール(クメン)1.0mmolの存在下で60分間の間99%の変換率で、数平均分子量Mn1700、多分散度(PDI)1.82及び末端ビニリデン二重結合含有量96mol%を有するポリイソブテンへと重合した。
純粋なイソブテン1.43g(25.5mmol)をジクロロメタン20ml及びn−ヘキサン5mlからの混合物中で−20℃で、三塩化アルミニウム及びジ−n−ブチルエーテル(モル比1:0.8)からの錯体(ジクロロメタン中の1モーラー溶液の形)0.62mmolを用いて、開始剤としての2−フェニル−2−プロパノール(クメン)0.5mmolの存在下で30分間の間44%の変換率で、数平均分子量Mn1550、多分散度(PDI)1.74及び末端ビニリデン二重結合含有量87mol%を有するポリイソブテンへと重合した。クメンにより開始したポリマー鎖の割合(leff)は56%であった。
「ラフィネート1」(純粋なイソブテン2.97g(53.0mmol)を含有)7.43gをジクロロメタン66ml中で−30℃で、三塩化アルミニウム及びジ−n−ブチルエーテル(モル比1:1)からの錯体(ジクロロメタン中の1モーラー溶液の形)2.15mmolを用いて、開始剤としての2−フェニル−2−プロパノール(クメン)1.0mmolの存在下で60分間の間30%の変換率で、数平均分子量Mn1720、多分散度(PDI)2.04及び末端ビニリデン二重結合含有量93mol%を有するポリイソブテンへと重合した。
純粋なイソブテン2.97g(53.0mmol)をジクロロメタン66ml中で−60℃で、三塩化アルミニウム及びジ−n−ブチルエーテル(モル比1:1)からの錯体(ジクロロメタン中の1モーラー溶液の形)1.43mmolを用いて、開始剤としての2−フェニル−2−プロパノール(クメン)1.0mmolの存在下で60分間の間100%の変換率で、数平均分子量Mn6005、多分散度(PDI)2.26及び末端ビニリデン二重結合含有量94mol%を有するポリイソブテンへと重合した。
純粋なイソブテン2.97g(53.0mmol)をジクロロメタン66ml中で−60℃で、三フッ化ホウ素及びメタノール(モル比1:1)からの錯体1.34mmolを用いて、60分間の間43%の変換率で、数平均分子量Mn4850、多分散度(PDI)4.05及び末端ビニリデン二重結合含有量62.5mol%のみを有するポリイソブテンへと重合した。
純粋なイソブテン1.43g(25.5mmol)をジクロロメタン20ml及びn−ヘキサン5mlからの混合物中で−40℃で、三塩化アルミニウム及びジ−n−ブチルエーテル(モル比1:1)からの錯体(ジクロロメタン中の1モーラー溶液の形)0.62mmolを用いて、開始剤としての1−フェニル−1−クロロエタン0.5mmolの存在下で30分間の間77%の変換率で、数平均分子量Mn2170、多分散度(PDI)1.99及び末端ビニリデン二重結合含有量88mol%を有するポリイソブテンへと重合した。1−フェニル−1−クロロエタンにより開始したポリマー鎖の割合(leff)は4%であった。
純粋なイソブテン1.43g(25.5mmol)をジクロロメタン20ml及びn−ヘキサン5mlからの混合物中で−20℃で、三塩化アルミニウム及びジ−n−ブチルエーテル(モル比1:1)からの錯体(ジクロロメタン中の1モーラー溶液の形)0.62mmolを用いて、開始剤としての1−(p−メトキシフェニル)エタノール0.5mmolの存在下で10分間の間26%の変換率で、数平均分子量Mn960、多分散度(PDI)1.05及び末端ビニリデン二重結合含有量88mol%を有するポリイソブテンへと重合した。
純粋なイソブテン1.43g(25.5mmol)をジクロロメタン15ml及びn−ヘキサン10mlからの混合物中で−60℃で、三塩化アルミニウム及びジ−n−ブチルエーテル(モル比1:1)からの錯体(ジクロロメタン中の1モーラー溶液の形)0.36mmolを用いて、開始剤としての2−フェニル−2−プロパノール(クメン)0.09mmol及び窒素含有塩基性化合物としてのピリジン0.0125molの存在下で30分間の間44%の変換率で、数平均分子量Mn2580、多分散度(PDI)1.86及び末端ビニリデン二重結合含有量90mol%を有するポリイソブテンへと重合した。クメンにより開始したポリマー鎖の割合(leff)は36%であった。
実施例15aを繰り返し、その際、反応期間を4倍にした:120分後に、53%の変換率で、数平均分子量Mn2490、多分散度(PDI)1.84及び末端ビニリデン二重結合含有量91mol%を有するポリイソブテンが得られた。クメンにより開始したポリマー鎖の割合(leff)は26%であった。
純粋なイソブテン1.43g(25.5mmol)をジクロロメタン15ml及びn−ヘキサン10mlからの混合物中で−20℃で、三塩化アルミニウム及びジ−n−ブチルエーテル(モル比1:1)からの錯体(ジクロロメタン中の1モーラー溶液の形)0.36mmolを用いて、開始剤としての2−フェニル−2−プロパノール(クメン)0.09mmol及び窒素含有塩基性化合物としてのピリジン0.0125molの存在下で120分間の間21%の変換率で、数平均分子量Mn1445、多分散度(PDI)1.69及び末端ビニリデン二重結合含有量94mol%を有するポリイソブテンへと重合した。クメンにより開始したポリマー鎖の割合(leff)は27%であった。
純粋なイソブテン1.43g(25.5mmol)をジクロロメタン20ml及びn−ヘキサン5mlからの混合物中で−40℃で、三塩化アルミニウム及びジ−n−ブチルエーテル(モル比1:1)からの錯体(ジクロロメタン中の1モーラー溶液の形)0.62mmolを用いて、開始剤としての2−フェニル−2−プロパノール(クメン)0.5mmol及び窒素含有塩基性化合物としてのピリジン0.0125molの存在下で30分間の間51%の変換率で、数平均分子量Mn1270、多分散度(PDI)1.17及び末端ビニリデン二重結合含有量91mol%を有するポリイソブテンへと重合した。クメンにより開始したポリマー鎖の割合(leff)は48%であった。
純粋なイソブテン1.43g(2.25mmol)をジクロロメタン20ml及びn−ヘキサン5mlからの混合物中で−20℃で、三塩化アルミニウム及びジ−n−ブチルエーテル(モル比1:1)からの錯体(ジクロロメタン中の1モーラー溶液の形)0.62mmolを用いて、開始剤としての1−フェニル−1−クロロエタン0.5mmolの存在下で3分間の間37%の変換率で、数平均分子量Mn3270、多分散度(PDI)1.76及び末端ビニリデン二重結合含有量97mol%を有するポリイソブテンへと重合した。
純粋なイソブテン1.43g(25.5mmol)をジクロロメタン20ml及びn−ヘキサン5mlからの混合物中で−20℃で、三塩化アルミニウム及びジ−n−ブチルエーテル(モル比1:1)からの錯体(ジクロロメタン中の1モーラー溶液の形)0.62mmolを用いて、開始剤としての1,4−ビス(1−ヒドロキシ−1−メチルエチル)ベンゼン0.25mmolの存在下で3分間の間36%の変換率で、数平均分子量Mn2750、多分散度(PDI)1.99及び末端ビニリデン二重結合含有量94mol%を有するポリイソブテンへと重合した。
純粋なイソブテン1.43g(25.5mmol)をジクロロメタン15ml及びn−ヘキサン10mlからの混合物中で−60℃で、三塩化アルミニウム及びジ−n−ブチルエーテル(モル比1:1)からの錯体(ジクロロメタン中の1モーラー溶液の形)0.36mmolを用いて120分間の間46%の変換率で、数平均分子量Mn7895、多分散度(PDI)2.23及び末端ビニリデン二重結合含有量94mol%を有するポリイソブテンへと重合した。
純粋なイソブテン1.43g(25.5mmol)をジクロロメタン25ml中で−20℃で、三塩化アルミニウム及びジ−n−ブチルエーテル(モル比1:1)からの錯体(ジクロロメタン中の1モーラー溶液の形)0.62mmolを用いて、開始剤としての水0.07mmolの存在下で3分間の間65%の変換率で、数平均分子量Mn2500、多分散度(PDI)1.92及び末端ビニリデン二重結合含有量92mol%を有するポリイソブテンへと重合した。
純粋なイソブテン1.43g(25.5mmol)をトルエン25ml中で−20℃で、三塩化アルミニウム及びジ−n−ブチルエーテル(モル比1:1)からの錯体(ジクロロメタン中の1モーラー溶液の形)0.62mmolを用いて、開始剤としての2−フェニル−2−プロパノール(クメン)0.5mmolの存在下で10分間の間19%の変換率で、数平均分子量Mn1030、多分散度(PDI)2.65及び末端ビニリデン二重結合含有量89mol%を有するポリイソブテンへと重合した。クメンにより開始したポリマー鎖の割合は98%(leff)であった。
純粋なイソブテン1.43g(25.5mmol)をトルエン15ml及びトリフルオロメチルベンゼン10mlからの混合物中で−20℃で、三塩化アルミニウム及びジ−n−ブチルエーテル(モル比1:1)からの錯体(ジクロロメタン中の1モーラー溶液の形)0.62mmolを用いて、開始剤としての2−フェニル−2−プロパノール(クメン)0.5mmolの存在下で3分間の間24%の変換率で、数平均分子量Mn1095、多分散度(PDI)1.93及び末端ビニリデン二重結合含有量78mol%を有するポリイソブテンへと重合した。クメンにより開始したポリマー鎖の割合(leff)は94%であった。
純粋なイソブテン3.00g(53mmol)をジクロロメタン50ml中で−60℃で、三塩化アルミニウム及びジ−n−ブチルエーテル(モル比1:1)からの錯体(ジクロロメタン中の1モーラー溶液の形)187.2mgを用いて、開始剤としての2−フェニル−2−プロパノール(クメン)24.5mgの存在下で120分間の間23%の変換率で、数平均分子量Mn3210、多分散度(PDI)1.90及び末端ビニリデン二重結合含有量>99mol%を有するポリイソブテンへと重合した。
純粋なイソブテン3.00g(53mmol)をジクロロメタン50ml中で−60℃で、三塩化アルミニウム及びジ−n−ブチルエーテル(モル比1:1)からの錯体(ジクロロメタン中の1モーラー溶液の形)1140mgを用いて、開始剤としての2−フェニル−2−プロパノール(クメン)24.5mgの存在下で120分間の間100%の変換率で、数平均分子量Mn4220、多分散度(PDI)2.05及び末端ビニリデン二重結合含有量>99mol%を有するポリイソブテンへと重合した。
「ラフィネート1」(純粋なイソブテン3.00g(53mmol)を含有する)7.50gをジクロロメタン50ml中で−60℃で、三塩化アルミニウム及びジ−n−ブチルエーテル(モル比1:1)からの錯体(ジクロロメタン中の1モーラー溶液の形)566.8mgを用いて、開始剤としての2−フェニル−2−プロパノール(クメン)24.5mgの存在下で60分間の間80%の変換率で、数平均分子量Mn4770、多分散度(PDI)2.67及び末端ビニリデン二重結合含有量96mol%を有するポリイソブテンへと重合した。
「ラフィネート1」(純粋なイソブテン27.7g(494mmol)を含有する)69.25gをオートクレーブ中で、in situでモル比1:1で製造した、三塩化アルミニウム及びジ−n−ブチルエーテルからの錯体6.54gを用いて、開始剤としての水0.43g(23.8mmol)の存在下で溶媒無しに0℃で60分間の間76%の変換率で、数平均分子量Mn965、多分散度(PDI)2.86及び末端ビニリデン二重結合含有量76mol%を有するポリイソブテンへと重合した。
「ラフィネート1」(純粋なイソブテン29.1g(519mmol)を含有する)72.75gをオートクレーブ中で、in situでモル比1:1で製造した、三塩化アルミニウム及びジ−n−ブチルエーテルからの錯体6.79gを用いて、開始剤としての水0.46g(25.4mmol)の存在下で溶媒無しに+20℃で60分間の間69%の変換率で、数平均分子量Mn800、多分散度(PDI)2.69及び末端ビニリデン二重結合含有量70mol%を有するポリイソブテンへと重合した。
「ラフィネート1」(純粋なイソブテン22.7g(405mmol)を含有する)56.75gをオートクレーブ中で、in situでモル比1:1で製造した、三塩化アルミニウム及びジ−n−ブチルエーテルからの錯体6.57gを用いて溶媒無しに、+20℃で60分間の間93%の変換率で、数平均分子量Mn1000、多分散度(PDI)2.90及び末端ビニリデン二重結合含有量76mol%を有するポリイソブテンへと重合した。
「ラフィネート1」(純粋なイソブテン24.9g(444mmol)を含有する)62.25gをオートクレーブ中で、in situでモル比1:1で製造した、三塩化アルミニウム及びジ−n−ブチルエーテルからの錯体6.56gを用いて溶媒無しに、0℃で60分間の間88%の変換率で、数平均分子量Mn1375、多分散度(PDI)2.94及び末端ビニリデン二重結合含有量69mol%を有するポリイソブテンへと重合した。
Claims (14)
- ポリイソブテン鎖末端あたり末端ビニリデン二重結合含有量少なくとも50mol%を有する高反応性イソブテンホモポリマー又はイソブテンコポリマーの製造方法において、イソブテン又はイソブテン含有モノマー混合物を、ドナーとして、少なくとも1のエーテル官能性又はカルボン酸エステル官能性を有する有機化合物を含有する、重合触媒として作用するアルミニウム三ハロゲン化物ドナー錯体又はアルミニウムアルキルハロゲン化物ドナー錯体の存在下で重合させることを特徴とする製造方法。
- イソブテン又はイソブテン含有モノマー混合物を、重合触媒として作用するアルミニウム三塩化物ドナー錯体の存在下で重合することを特徴とする請求項1記載の方法。
- ドナーとして、一般式R1−O−R2(式中、可変部R1及びR2は、相互に独立してC1〜C20−アルキル基、C5〜C8−シクロアルキル基、C6〜C20−アリール基又はC7〜C20−アリールアルキル基である)のジヒドロカルビルエーテルを含有するアルミニウム三ハロゲン化物ドナー錯体又はアルミニウムアルキルハロゲン化物ドナー錯体を使用することを特徴とする請求項1又は2記載の方法。
- ドナーとして、一般式R3−COOR4(式中、可変部R3及びR4は、相互に独立してC1〜C20−アルキル基、C5〜C8−シクロアルキル基、C6〜C20−アリール基又はC7〜C20−アリールアルキル基である)のカルボン酸ヒドロカルビルエステルを含有するアルミニウム三ハロゲン化物ドナー錯体又はアルミニウムアルキルハロゲン化物ドナー錯体を使用することを特徴とする請求項1又は2記載の方法。
- ドナー化合物が3〜16個の全炭素数を有する、アルミニウム三ハロゲン化物ドナー錯体又はアルミニウムアルキルハロゲン化物ドナー錯体を使用することを特徴とする請求項1から4のいずれか1項記載の方法。
- 重合を、1又は複数のヒドロキシル基がそれぞれ1のsp3混成した炭素原子に結合している有機ヒドロキシ化合物、1又は複数のハロゲン原子がそれぞれ1のsp3混成した炭素原子に結合している有機ハロゲン化合物、及び、水から選択されている、一官能性又は多官能性開始剤の併用下で実施することを特徴とする請求項1から5のいずれか1項記載の方法。
- 開始剤が、水、メタノール、エタノール、1−フェニルエタノール、1−(p−メトキシフェニル)エタノール、n−プロパノール、イソプロパノール、2−フェニル−2−プロパノール、n−ブタノール、イソブタノール、sec−ブタノール、tert−ブタノール、1−フェニル−1−クロロエタン、2−フェニル−2−クロロプロパン、tert−ブチルクロリド及び1,3−又は1,4−ビス(1−ヒドロキシ−1−メチルエチル)ベンゼンから選択されていることを特徴とする請求項6記載の方法。
- 重合を、それぞれ、イソブテンの単独重合の場合には使用されるイソブテンモノマー1molに対して、又は、イソブテンの共重合の場合には使用される重合可能なモノマー全量の1molに対して、0.01〜10mmolの窒素含有塩基性化合物の存在下で実施することを特徴とする請求項1から7のいずれか1項記載の方法。
- 窒素含有塩基性化合物としてピリジン又はピリジン誘導体を使用することを特徴とする請求項8記載の方法。
- 数平均分子量Mn500〜250000を有する高反応性イソブテンホモポリマー又はイソブテンコポリマーの製造をするための、請求項1から9のいずれか1項記載の方法。
- 多分散度1.05から3.5未満を有する高反応性イソブテンホモポリマー又はイソブテンコポリマーを製造するための、請求項1から10のいずれか1項記載の方法。
- 重合を−60℃〜−15℃の温度で実施することを特徴とする請求項1から11のいずれか1項記載の方法。
- 重合を、不活性希釈剤としての、ハロゲン化脂肪族炭化水素中で、又は、ハロゲン化脂肪族炭化水素からの混合物中で、又は、少なくとも1のハロゲン化脂肪族炭化水素と少なくとも1の脂肪族、脂環式又は芳香族炭化水素とからの混合物中で実施することを特徴とする請求項1から12のいずれか1項記載の方法。
- 一般式I
R10、R11及びR12は、相互に独立して水素、C1〜C20−アルキル、C5〜C8−シクロアルキル、C6〜C20−アリール、C7〜C20−アルキルアリール又はフェニル、その際、芳香族核はさらに1又は複数のC1〜C4−アルキル基又はC1〜C4−アルコキシ基又は一般式II
その際、可変部R10、R11又はR12の最高で1つが水素を意味し、かつ、可変部R10、R11又はR12の少なくとも1がフェニルであり、これはさらに1又は複数のC1〜C4−アルキル基又はC1〜C4−アルコキシ基又は一般式IIの原子団を置換基として有することができる、かつ
nは9〜4500の数である]
のイソブテンポリマー。
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SG10201500721PA (en) * | 2010-02-17 | 2015-04-29 | Basf Se | Method for producing highly reactive isobutene homo or copolymers |
US9562117B2 (en) | 2010-11-30 | 2017-02-07 | Basf Se | Preparation of derivatives of isobutene copolymers |
US9296841B2 (en) * | 2010-11-30 | 2016-03-29 | Basf Se | Preparation of isobutene homo- or copolymer derivatives |
US8697820B2 (en) | 2011-08-11 | 2014-04-15 | Basf Se | Process for preparing high-reactivity isobutene homo- or copolymers |
US9458262B2 (en) | 2011-10-21 | 2016-10-04 | Basf Se | Process for preparing isobutene homopolymers or copolymers |
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US9156924B2 (en) * | 2013-03-12 | 2015-10-13 | University Of Massachusetts | Polymerization initiating system and method to produce highly reactive olefin functional polymers |
US9631038B2 (en) * | 2013-10-11 | 2017-04-25 | University Of Massachusetts | Polymerization initiating system and method to produce highly reactive olefin functional polymers |
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AR080195A1 (es) | 2012-03-21 |
CN107033265A (zh) | 2017-08-11 |
WO2011101281A1 (de) | 2011-08-25 |
RU2012139361A (ru) | 2014-03-27 |
KR101797789B1 (ko) | 2017-11-15 |
CN102762610A (zh) | 2012-10-31 |
SG182759A1 (en) | 2012-09-27 |
KR20130008551A (ko) | 2013-01-22 |
CA2789843A1 (en) | 2011-08-25 |
BR112012020302A2 (pt) | 2020-07-28 |
JP5798130B2 (ja) | 2015-10-21 |
SG10201500721PA (en) | 2015-04-29 |
BR112012020302B1 (pt) | 2021-08-17 |
JP2013519766A (ja) | 2013-05-30 |
MY156799A (en) | 2016-03-31 |
EP2536768B1 (de) | 2015-04-08 |
RU2555400C2 (ru) | 2015-07-10 |
EP2536768A1 (de) | 2012-12-26 |
JP6099708B2 (ja) | 2017-03-22 |
CA2789843C (en) | 2018-07-10 |
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