CN101775092A - 高异戊二烯丁基橡胶的生产方法 - Google Patents
高异戊二烯丁基橡胶的生产方法 Download PDFInfo
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- CN101775092A CN101775092A CN201010110172A CN201010110172A CN101775092A CN 101775092 A CN101775092 A CN 101775092A CN 201010110172 A CN201010110172 A CN 201010110172A CN 201010110172 A CN201010110172 A CN 201010110172A CN 101775092 A CN101775092 A CN 101775092A
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- polymkeric substance
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- repeating unit
- derived
- isoolefine
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- 229920005549 butyl rubber Polymers 0.000 title description 12
- 238000004519 manufacturing process Methods 0.000 title description 4
- 238000000034 method Methods 0.000 claims abstract description 47
- 239000000178 monomer Substances 0.000 claims abstract description 45
- 239000000126 substance Substances 0.000 claims abstract description 45
- -1 polyene hydrocarbon Chemical class 0.000 claims abstract description 37
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract description 32
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 32
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 23
- 238000007334 copolymerization reaction Methods 0.000 claims abstract description 14
- 241001441571 Hiodontidae Species 0.000 claims abstract description 9
- 150000002828 nitro derivatives Chemical class 0.000 claims abstract description 9
- 150000002736 metal compounds Chemical class 0.000 claims abstract description 6
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical group CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 claims description 47
- 238000006116 polymerization reaction Methods 0.000 claims description 26
- 239000000203 mixture Substances 0.000 claims description 16
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims description 15
- XZKRXPZXQLARHH-UHFFFAOYSA-N buta-1,3-dienylbenzene Chemical group C=CC=CC1=CC=CC=C1 XZKRXPZXQLARHH-UHFFFAOYSA-N 0.000 claims description 8
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 claims description 6
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 claims description 5
- NFWSQSCIDYBUOU-UHFFFAOYSA-N methylcyclopentadiene Chemical compound CC1=CC=CC1 NFWSQSCIDYBUOU-UHFFFAOYSA-N 0.000 claims description 3
- SBYMUDUGTIKLCR-UHFFFAOYSA-N 2-chloroethenylbenzene Chemical compound ClC=CC1=CC=CC=C1 SBYMUDUGTIKLCR-UHFFFAOYSA-N 0.000 claims description 2
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 claims description 2
- 230000009466 transformation Effects 0.000 abstract description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 5
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 28
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical group CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 13
- 229920001971 elastomer Polymers 0.000 description 11
- 239000000463 material Substances 0.000 description 11
- 229940050176 methyl chloride Drugs 0.000 description 11
- 229920000642 polymer Polymers 0.000 description 11
- 150000001875 compounds Chemical class 0.000 description 10
- 239000003054 catalyst Substances 0.000 description 9
- 125000001931 aliphatic group Chemical group 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 150000002500 ions Chemical class 0.000 description 5
- 239000002002 slurry Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- WTARULDDTDQWMU-RKDXNWHRSA-N (+)-β-pinene Chemical compound C1[C@H]2C(C)(C)[C@@H]1CCC2=C WTARULDDTDQWMU-RKDXNWHRSA-N 0.000 description 4
- WTARULDDTDQWMU-IUCAKERBSA-N (-)-Nopinene Natural products C1[C@@H]2C(C)(C)[C@H]1CCC2=C WTARULDDTDQWMU-IUCAKERBSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- VHOQXEIFYTTXJU-UHFFFAOYSA-N Isobutylene-isoprene copolymer Chemical group CC(C)=C.CC(=C)C=C VHOQXEIFYTTXJU-UHFFFAOYSA-N 0.000 description 4
- WTARULDDTDQWMU-UHFFFAOYSA-N Pseudopinene Natural products C1C2C(C)(C)C1CCC2=C WTARULDDTDQWMU-UHFFFAOYSA-N 0.000 description 4
- XCPQUQHBVVXMRQ-UHFFFAOYSA-N alpha-Fenchene Natural products C1CC2C(=C)CC1C2(C)C XCPQUQHBVVXMRQ-UHFFFAOYSA-N 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 229930006722 beta-pinene Natural products 0.000 description 4
- LCWMKIHBLJLORW-UHFFFAOYSA-N gamma-carene Natural products C1CC(=C)CC2C(C)(C)C21 LCWMKIHBLJLORW-UHFFFAOYSA-N 0.000 description 4
- 239000008187 granular material Substances 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 229910052723 transition metal Inorganic materials 0.000 description 4
- 150000003624 transition metals Chemical class 0.000 description 4
- AIDLAEPHWROGFI-UHFFFAOYSA-N 2-methylbenzene-1,3-dicarboxylic acid Chemical compound CC1=C(C(O)=O)C=CC=C1C(O)=O AIDLAEPHWROGFI-UHFFFAOYSA-N 0.000 description 3
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- 125000003118 aryl group Chemical class 0.000 description 3
- 230000031709 bromination Effects 0.000 description 3
- 238000005893 bromination reaction Methods 0.000 description 3
- 150000001721 carbon Chemical group 0.000 description 3
- 238000005660 chlorination reaction Methods 0.000 description 3
- 238000010924 continuous production Methods 0.000 description 3
- 150000001993 dienes Chemical class 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 229920005555 halobutyl Polymers 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000005987 sulfurization reaction Methods 0.000 description 3
- ZJQIXGGEADDPQB-UHFFFAOYSA-N 1,2-bis(ethenyl)-3,4-dimethylbenzene Chemical compound CC1=CC=C(C=C)C(C=C)=C1C ZJQIXGGEADDPQB-UHFFFAOYSA-N 0.000 description 2
- WAEOXIOXMKNFLQ-UHFFFAOYSA-N 1-methyl-4-prop-2-enylbenzene Chemical group CC1=CC=C(CC=C)C=C1 WAEOXIOXMKNFLQ-UHFFFAOYSA-N 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- BKOOMYPCSUNDGP-UHFFFAOYSA-N 2-methylbut-2-ene Chemical compound CC=C(C)C BKOOMYPCSUNDGP-UHFFFAOYSA-N 0.000 description 2
- WSSSPWUEQFSQQG-UHFFFAOYSA-N 4-methyl-1-pentene Chemical compound CC(C)CC=C WSSSPWUEQFSQQG-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 2
- 235000021355 Stearic acid Nutrition 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- MPMBRWOOISTHJV-UHFFFAOYSA-N but-1-enylbenzene Chemical compound CCC=CC1=CC=CC=C1 MPMBRWOOISTHJV-UHFFFAOYSA-N 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000001879 gelation Methods 0.000 description 2
- 239000003292 glue Substances 0.000 description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 2
- SSDSCDGVMJFTEQ-UHFFFAOYSA-N octadecyl 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 SSDSCDGVMJFTEQ-UHFFFAOYSA-N 0.000 description 2
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- DBSDMAPJGHBWAL-UHFFFAOYSA-N penta-1,4-dien-3-ylbenzene Chemical compound C=CC(C=C)C1=CC=CC=C1 DBSDMAPJGHBWAL-UHFFFAOYSA-N 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 238000005096 rolling process Methods 0.000 description 2
- 239000008117 stearic acid Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 229920003048 styrene butadiene rubber Polymers 0.000 description 2
- 125000003944 tolyl group Chemical group 0.000 description 2
- 230000005068 transpiration Effects 0.000 description 2
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 description 2
- 125000005023 xylyl group Chemical group 0.000 description 2
- 150000003755 zirconium compounds Chemical class 0.000 description 2
- APPOKADJQUIAHP-GGWOSOGESA-N (2e,4e)-hexa-2,4-diene Chemical compound C\C=C\C=C\C APPOKADJQUIAHP-GGWOSOGESA-N 0.000 description 1
- AFVDZBIIBXWASR-AATRIKPKSA-N (E)-1,3,5-hexatriene Chemical compound C=C\C=C\C=C AFVDZBIIBXWASR-AATRIKPKSA-N 0.000 description 1
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical group C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 description 1
- JLSUFZZPRVNDIW-UHFFFAOYSA-N 1-ethenylcyclohexa-1,3-diene Chemical compound C=CC1=CC=CCC1 JLSUFZZPRVNDIW-UHFFFAOYSA-N 0.000 description 1
- DZPCYXCBXGQBRN-UHFFFAOYSA-N 2,5-Dimethyl-2,4-hexadiene Chemical compound CC(C)=CC=C(C)C DZPCYXCBXGQBRN-UHFFFAOYSA-N 0.000 description 1
- RCJMVGJKROQDCB-UHFFFAOYSA-N 2-methylpenta-1,3-diene Chemical compound CC=CC(C)=C RCJMVGJKROQDCB-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
- INYHZQLKOKTDAI-UHFFFAOYSA-N 5-ethenylbicyclo[2.2.1]hept-2-ene Chemical compound C1C2C(C=C)CC1C=C2 INYHZQLKOKTDAI-UHFFFAOYSA-N 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- 229920002943 EPDM rubber Polymers 0.000 description 1
- 229920002449 FKM Polymers 0.000 description 1
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 1
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 1
- 229920000459 Nitrile rubber Polymers 0.000 description 1
- AYDQIZKZTQHYIY-UHFFFAOYSA-N OC(=O)C1(C)CC(C(O)=O)=CC=C1 Chemical compound OC(=O)C1(C)CC(C(O)=O)=CC=C1 AYDQIZKZTQHYIY-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 1
- 238000006887 Ullmann reaction Methods 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000004411 aluminium Substances 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- IMJGQTCMUZMLRZ-UHFFFAOYSA-N buta-1,3-dien-2-ylbenzene Chemical compound C=CC(=C)C1=CC=CC=C1 IMJGQTCMUZMLRZ-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical compound [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 238000013016 damping Methods 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- YNLAOSYQHBDIKW-UHFFFAOYSA-M diethylaluminium chloride Chemical compound CC[Al](Cl)CC YNLAOSYQHBDIKW-UHFFFAOYSA-M 0.000 description 1
- UAIZDWNSWGTKFZ-UHFFFAOYSA-L ethylaluminum(2+);dichloride Chemical compound CC[Al](Cl)Cl UAIZDWNSWGTKFZ-UHFFFAOYSA-L 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 229910052733 gallium Inorganic materials 0.000 description 1
- 150000002363 hafnium compounds Chemical class 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 125000004968 halobutyl group Chemical group 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229920006168 hydrated nitrile rubber Polymers 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000002779 inactivation Effects 0.000 description 1
- 125000003454 indenyl group Chemical class C1(C=CC2=CC=CC=C12)* 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052752 metalloid Inorganic materials 0.000 description 1
- 150000002738 metalloids Chemical class 0.000 description 1
- CPOFMOWDMVWCLF-UHFFFAOYSA-N methyl(oxo)alumane Chemical compound C[Al]=O CPOFMOWDMVWCLF-UHFFFAOYSA-N 0.000 description 1
- SJYNFBVQFBRSIB-UHFFFAOYSA-N norbornadiene Chemical compound C1=CC2C=CC1C2 SJYNFBVQFBRSIB-UHFFFAOYSA-N 0.000 description 1
- 125000005574 norbornylene group Chemical group 0.000 description 1
- 239000012038 nucleophile Substances 0.000 description 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Natural products CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000000979 retarding effect Effects 0.000 description 1
- 238000010517 secondary reaction Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000004646 sulfenyl group Chemical group S(*)* 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- JTJFQBNJBPPZRI-UHFFFAOYSA-J vanadium tetrachloride Chemical class Cl[V](Cl)(Cl)Cl JTJFQBNJBPPZRI-UHFFFAOYSA-J 0.000 description 1
- 238000004073 vulcanization Methods 0.000 description 1
- 239000003643 water by type Substances 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
- C08F210/00—Copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
- C08F210/04—Monomers containing three or four carbon atoms
- C08F210/08—Butenes
- C08F210/10—Isobutene
- C08F210/12—Isobutene with conjugated diolefins, e.g. butyl rubber
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)
- Polymerization Catalysts (AREA)
- Polymerisation Methods In General (AREA)
- Graft Or Block Polymers (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA2418884A CA2418884C (en) | 2003-02-14 | 2003-02-14 | Process for production of high-isoprene butyl rubber |
| CA2418884 | 2003-02-14 |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN200410028455.0A Division CN1526745B (zh) | 2003-02-14 | 2004-02-13 | 高异戊二烯丁基橡胶的生产方法 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
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| EP (1) | EP1449859B1 (https=) |
| JP (2) | JP5081369B2 (https=) |
| CN (2) | CN101775092A (https=) |
| CA (1) | CA2418884C (https=) |
| RU (1) | RU2333224C2 (https=) |
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| CN106536618A (zh) * | 2014-04-30 | 2017-03-22 | 阿朗新科新加坡私人有限公司 | 高不饱和多峰聚异烯烃组合物及其制备方法 |
| CN117264336A (zh) * | 2023-10-24 | 2023-12-22 | 安徽中马橡塑科技有限公司 | 一种医用低渗透预灌封胶塞及其制备方法 |
Families Citing this family (37)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2458741A1 (en) * | 2004-02-23 | 2005-08-23 | Rui Resendes | Peroxide curable butyl formulations containing high-isoprene butyl rubber |
| US20090299000A1 (en) * | 2005-08-26 | 2009-12-03 | Rui Resendes | Peroxide curable rubber compound containing high multiolefin halobutyl ionomers |
| WO2007022643A1 (en) * | 2005-08-26 | 2007-03-01 | Lanxess Inc. | Peroxide curable rubber compound containing high multiolefin halobutyl ionomers |
| US20090182095A1 (en) * | 2005-08-26 | 2009-07-16 | Lanxess Inc. | Process for production of peroxide curable high multiolefin halobutyl ionomers |
| CA2578583C (en) * | 2006-03-14 | 2014-06-03 | Lanxess Inc. | Butyl ionomer having improved surface adhesion |
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| CA2696102C (en) * | 2007-08-31 | 2012-09-11 | Exxonmobil Chemical Patents Inc. | Method for reducing depositions in polymerization vessels |
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| MX2011008524A (es) | 2009-02-13 | 2011-09-08 | Lanxess Inc | Ionomeros de butilo reciclados y procesos de reciclado. |
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| US9796794B2 (en) | 2012-12-20 | 2017-10-24 | LANXSS, Inc. | Ionomer comprising pendant vinyl groups and processes for preparing same |
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| EP3015521A1 (en) | 2014-10-29 | 2016-05-04 | Lanxess Inc. | Hot melt adhesives with butyl ionomer |
| EP2966097A1 (en) | 2014-07-07 | 2016-01-13 | Lanxess Inc. | Ultrafiltration of polyisoolefin copolymers |
| US10044570B2 (en) * | 2014-08-22 | 2018-08-07 | Vmware, Inc. | Policy management system with proactive and reactive monitoring and enforcement |
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| KR20170056569A (ko) * | 2014-09-10 | 2017-05-23 | 스미또모 가가꾸 가부시끼가이샤 | 공액 디엔 중합체 및 공액 디엔 중합체 조성물 |
| EP3072909A1 (en) | 2015-03-25 | 2016-09-28 | Lanxess Inc. | Halogenated polyisoolefins with reduced halogenated oligomers |
| EP3178889A1 (en) | 2015-12-11 | 2017-06-14 | Lanxess Inc. | Elastomeric coatings |
| EP3231820A1 (en) | 2016-04-15 | 2017-10-18 | ARLANXEO Canada Inc. | Polymer compositions having a halo-containing polymer with a multi-functional phosphine linkage |
| EP3694894B1 (en) * | 2017-10-14 | 2025-05-21 | TPC Group LLC | Isobutylene copolymers, method for making isobutylene copolymers and isobutylene copolymer products |
| EP3807081A1 (en) * | 2018-06-13 | 2021-04-21 | ARLANXEO Deutschland GmbH | Sealing compounds for self-sealing tyres |
| CN118946597A (zh) * | 2022-03-28 | 2024-11-12 | 旭化成株式会社 | 多官能乙烯基芳香族共聚物 |
| CN116253824A (zh) * | 2023-02-20 | 2023-06-13 | 北京化工大学 | 一种α-蒎烯烃裂解物及其衍生物、异丁烯与二烯烃的三元共聚物及其制备方法 |
Family Cites Families (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2356128A (en) * | 1939-10-20 | 1944-08-22 | Jasco Inc | Mixed olefinic polymerization process and product |
| NL170646B (nl) * | 1951-06-30 | Western Electric Co | Werkwijze voor het in een vlak oppervlak van een voorwerp vormen van verdiepte delen. | |
| US2781334A (en) * | 1952-05-01 | 1957-02-12 | Exxon Research Engineering Co | Divinyl aromatic modified isoolefinmultiolefin copolymers |
| US3099644A (en) * | 1959-10-06 | 1963-07-30 | Exxon Research Engineering Co | Continuous chlorination and bromination of butyl rubber |
| US4031300A (en) * | 1974-04-01 | 1977-06-21 | Exxon Research And Engineering Company | High molecular weight, high unsaturation isobutylene-cyclopentadiene copolymers |
| US4171414A (en) | 1977-08-25 | 1979-10-16 | Exxon Research & Engineering Co. | Catalyst composition for an improved polymerization process of isoolefins and multiolefins |
| US4269955A (en) * | 1977-08-25 | 1981-05-26 | Exxon Research & Engineering Company | Catalyst composition polymerization of isoolefins and multiolefins |
| US4215022A (en) * | 1978-10-16 | 1980-07-29 | Exxon Research & Engineering Co. | Isobutylene cyclodiolefin copolymers and terpolymers |
| JPH0627127B2 (ja) * | 1985-02-13 | 1994-04-13 | 日本ゼオン株式会社 | 炭化水素樹脂の製造方法 |
| CA1283997C (en) * | 1986-12-12 | 1991-05-07 | Frank Joung-Yei Chen | Fixed bed process for polymerizing liquid butenes |
| US5194538A (en) * | 1992-07-15 | 1993-03-16 | Polysar Corporation | Preparation of butyl rubber with bimodal molecular weight distribution |
| CA2200688A1 (en) * | 1995-07-27 | 1997-02-13 | Chang Sun Chu | The process for preparing isobutene-cyclodiene copolymers |
| DE19627529A1 (de) | 1996-07-09 | 1998-01-15 | Bayer Ag | Neue, vanadiumhaltige Initiatorsysteme für die (Co)polymerisation von Isoolefinen |
| CA2257701A1 (en) | 1998-12-31 | 2000-06-30 | Bayer Inc. | Improved cationic polymerization process and catalyst system therefor |
| DE10004048A1 (de) * | 2000-01-31 | 2001-08-02 | Bayer Ag | Hochmolekulare gelfreie Isobutencopolymere mit hohen Doppelbindungsgehalten |
| US6605680B1 (en) * | 2000-04-07 | 2003-08-12 | Eastman Chemical Resins, Inc. | Low color, aromatic modified C5 hydrocarbon resins |
| CA2316741A1 (en) | 2000-08-24 | 2002-02-24 | Bayer Inc. | Improved processability butyl rubber and process for production thereof |
| DE10042118A1 (de) * | 2000-08-28 | 2002-03-14 | Bayer Ag | Verfahren zur Herstellung von Isoolefincopolymeren |
| CA2413611C (en) * | 2002-12-05 | 2012-11-13 | Bayer Inc. | Process for production of high-isoprene butyl rubber |
-
2003
- 2003-02-14 CA CA2418884A patent/CA2418884C/en not_active Expired - Lifetime
-
2004
- 2004-02-06 EP EP04002665.0A patent/EP1449859B1/en not_active Expired - Lifetime
- 2004-02-11 US US10/776,761 patent/US7282548B2/en not_active Expired - Lifetime
- 2004-02-13 CN CN201010110172A patent/CN101775092A/zh active Pending
- 2004-02-13 RU RU2004104108/04A patent/RU2333224C2/ru active
- 2004-02-13 CN CN200410028455.0A patent/CN1526745B/zh not_active Expired - Fee Related
- 2004-02-16 JP JP2004037892A patent/JP5081369B2/ja not_active Expired - Fee Related
-
2007
- 2007-08-31 US US11/897,828 patent/US7446151B2/en not_active Expired - Lifetime
-
2008
- 2008-09-23 US US12/235,861 patent/US20090018289A1/en not_active Abandoned
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2011
- 2011-06-01 JP JP2011123544A patent/JP5613624B2/ja not_active Expired - Fee Related
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106536618A (zh) * | 2014-04-30 | 2017-03-22 | 阿朗新科新加坡私人有限公司 | 高不饱和多峰聚异烯烃组合物及其制备方法 |
| CN106536618B (zh) * | 2014-04-30 | 2019-04-16 | 阿朗新科新加坡私人有限公司 | 高不饱和多峰聚异烯烃组合物及其制备方法 |
| CN117264336A (zh) * | 2023-10-24 | 2023-12-22 | 安徽中马橡塑科技有限公司 | 一种医用低渗透预灌封胶塞及其制备方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| CA2418884A1 (en) | 2004-08-14 |
| CA2418884C (en) | 2010-07-20 |
| JP5081369B2 (ja) | 2012-11-28 |
| CN1526745A (zh) | 2004-09-08 |
| JP2004244638A (ja) | 2004-09-02 |
| US20070299229A1 (en) | 2007-12-27 |
| EP1449859A1 (en) | 2004-08-25 |
| CN1526745B (zh) | 2010-12-08 |
| US7282548B2 (en) | 2007-10-16 |
| EP1449859B1 (en) | 2014-04-09 |
| HK1069406A1 (en) | 2005-05-20 |
| US20090018289A1 (en) | 2009-01-15 |
| US20050043440A1 (en) | 2005-02-24 |
| JP5613624B2 (ja) | 2014-10-29 |
| RU2333224C2 (ru) | 2008-09-10 |
| RU2004104108A (ru) | 2005-07-27 |
| US7446151B2 (en) | 2008-11-04 |
| JP2011168796A (ja) | 2011-09-01 |
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