CA1094743A - Continuous solution polymerization of a conjugated diene with a monovinylaromatic compound using alkoxysilicon treating agents in the first reactor means of a reactor series - Google Patents
Continuous solution polymerization of a conjugated diene with a monovinylaromatic compound using alkoxysilicon treating agents in the first reactor means of a reactor seriesInfo
- Publication number
- CA1094743A CA1094743A CA276,888A CA276888A CA1094743A CA 1094743 A CA1094743 A CA 1094743A CA 276888 A CA276888 A CA 276888A CA 1094743 A CA1094743 A CA 1094743A
- Authority
- CA
- Canada
- Prior art keywords
- process according
- polymerization
- alkoxysilicon
- compound
- conjugated diene
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 56
- 150000001993 dienes Chemical class 0.000 title claims abstract description 41
- 238000010528 free radical solution polymerization reaction Methods 0.000 title claims abstract description 6
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 53
- 229920001577 copolymer Polymers 0.000 claims abstract description 5
- 238000000034 method Methods 0.000 claims description 38
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 34
- 239000003795 chemical substances by application Substances 0.000 claims description 32
- 239000000178 monomer Substances 0.000 claims description 31
- 239000003999 initiator Substances 0.000 claims description 30
- 239000000203 mixture Substances 0.000 claims description 24
- 239000003085 diluting agent Substances 0.000 claims description 19
- 229930195733 hydrocarbon Natural products 0.000 claims description 19
- 150000002430 hydrocarbons Chemical class 0.000 claims description 18
- -1 alkali metal salt Chemical class 0.000 claims description 17
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 claims description 16
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 16
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 15
- 125000001979 organolithium group Chemical group 0.000 claims description 15
- 239000004215 Carbon black (E152) Substances 0.000 claims description 13
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 13
- 229910052744 lithium Inorganic materials 0.000 claims description 13
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 claims description 12
- 150000001491 aromatic compounds Chemical class 0.000 claims description 10
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 claims description 8
- BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical group CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 claims description 8
- 229920005604 random copolymer Polymers 0.000 claims description 8
- 229910052783 alkali metal Inorganic materials 0.000 claims description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- 125000004429 atom Chemical group 0.000 claims description 6
- 229910052700 potassium Inorganic materials 0.000 claims description 6
- VXEGSRKPIUDPQT-UHFFFAOYSA-N 4-[4-(4-methoxyphenyl)piperazin-1-yl]aniline Chemical compound C1=CC(OC)=CC=C1N1CCN(C=2C=CC(N)=CC=2)CC1 VXEGSRKPIUDPQT-UHFFFAOYSA-N 0.000 claims description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 5
- 150000002900 organolithium compounds Chemical class 0.000 claims description 5
- 239000005049 silicon tetrachloride Substances 0.000 claims description 5
- SDJHPPZKZZWAKF-UHFFFAOYSA-N 2,3-dimethylbuta-1,3-diene Chemical compound CC(=C)C(C)=C SDJHPPZKZZWAKF-UHFFFAOYSA-N 0.000 claims description 4
- 150000001340 alkali metals Chemical class 0.000 claims description 4
- 238000007334 copolymerization reaction Methods 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- ZRLVQFQTCMUIRM-UHFFFAOYSA-N potassium;2-methylbutan-2-olate Chemical group [K+].CCC(C)(C)[O-] ZRLVQFQTCMUIRM-UHFFFAOYSA-N 0.000 claims description 4
- 239000011541 reaction mixture Substances 0.000 claims description 4
- 229910052710 silicon Inorganic materials 0.000 claims description 4
- 239000010703 silicon Substances 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 3
- 239000006085 branching agent Substances 0.000 claims description 3
- WGOPGODQLGJZGL-UHFFFAOYSA-N lithium;butane Chemical compound [Li+].CC[CH-]C WGOPGODQLGJZGL-UHFFFAOYSA-N 0.000 claims description 3
- SZAVVKVUMPLRRS-UHFFFAOYSA-N lithium;propane Chemical compound [Li+].C[CH-]C SZAVVKVUMPLRRS-UHFFFAOYSA-N 0.000 claims description 3
- 150000002894 organic compounds Chemical class 0.000 claims description 3
- NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 claims description 3
- 150000005846 sugar alcohols Polymers 0.000 claims description 3
- 150000003568 thioethers Chemical class 0.000 claims description 3
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical group C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 claims description 2
- VDNSZPNSUQRUMS-UHFFFAOYSA-N 1-cyclohexyl-4-ethenylbenzene Chemical compound C1=CC(C=C)=CC=C1C1CCCCC1 VDNSZPNSUQRUMS-UHFFFAOYSA-N 0.000 claims description 2
- WJNKJKGZKFOLOJ-UHFFFAOYSA-N 1-dodecyl-4-ethenylbenzene Chemical compound CCCCCCCCCCCCC1=CC=C(C=C)C=C1 WJNKJKGZKFOLOJ-UHFFFAOYSA-N 0.000 claims description 2
- JZHGRUMIRATHIU-UHFFFAOYSA-N 1-ethenyl-3-methylbenzene Chemical compound CC1=CC=CC(C=C)=C1 JZHGRUMIRATHIU-UHFFFAOYSA-N 0.000 claims description 2
- RRRXUCMQOPNVAT-UHFFFAOYSA-N 1-ethenyl-4-(4-methylphenyl)benzene Chemical compound C1=CC(C)=CC=C1C1=CC=C(C=C)C=C1 RRRXUCMQOPNVAT-UHFFFAOYSA-N 0.000 claims description 2
- JHTICDZLXFNVKL-UHFFFAOYSA-N 1-ethenyl-4-(4-phenylbutyl)benzene Chemical compound C1=CC(C=C)=CC=C1CCCCC1=CC=CC=C1 JHTICDZLXFNVKL-UHFFFAOYSA-N 0.000 claims description 2
- VVTGQMLRTKFKAM-UHFFFAOYSA-N 1-ethenyl-4-propylbenzene Chemical compound CCCC1=CC=C(C=C)C=C1 VVTGQMLRTKFKAM-UHFFFAOYSA-N 0.000 claims description 2
- DXFURPHVJQITAC-UHFFFAOYSA-N 4-benzyl-1-ethenyl-2-ethylbenzene Chemical compound C1=C(C=C)C(CC)=CC(CC=2C=CC=CC=2)=C1 DXFURPHVJQITAC-UHFFFAOYSA-N 0.000 claims description 2
- UGWOAPBVIGCNOV-UHFFFAOYSA-N 5-ethenyldec-5-ene Chemical compound CCCCC=C(C=C)CCCC UGWOAPBVIGCNOV-UHFFFAOYSA-N 0.000 claims description 2
- LNCNKWLTFCQSHO-UHFFFAOYSA-N C1=CC([Li])=CC=C1C1=CC=C([Li])C=C1 Chemical group C1=CC([Li])=CC=C1C1=CC=C([Li])C=C1 LNCNKWLTFCQSHO-UHFFFAOYSA-N 0.000 claims description 2
- SSFGWDHVAMCZMG-UHFFFAOYSA-N C1=CC=C2C([Li])=CC=C([Li])C2=C1 Chemical compound C1=CC=C2C([Li])=CC=C([Li])C2=C1 SSFGWDHVAMCZMG-UHFFFAOYSA-N 0.000 claims description 2
- VIXXKNNHPJPCOF-UHFFFAOYSA-N C=1C=CC=CC=1C([Li])C([Li])CCCCCCC1=CC=CC=C1 Chemical compound C=1C=CC=CC=1C([Li])C([Li])CCCCCCC1=CC=CC=C1 VIXXKNNHPJPCOF-UHFFFAOYSA-N 0.000 claims description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 2
- PYWOMDDOXZOOJZ-UHFFFAOYSA-N [Li]C1=CC=C([Li])C=C1 Chemical compound [Li]C1=CC=C([Li])C=C1 PYWOMDDOXZOOJZ-UHFFFAOYSA-N 0.000 claims description 2
- LURCBQOZOZIVCW-UHFFFAOYSA-N [Li]C1CC([Li])C([Li])C([Li])C1 Chemical compound [Li]C1CC([Li])C([Li])C([Li])C1 LURCBQOZOZIVCW-UHFFFAOYSA-N 0.000 claims description 2
- NTHIUKNPTBFSFZ-UHFFFAOYSA-N [Li]C1CC([Li])CC([Li])C1 Chemical compound [Li]C1CC([Li])CC([Li])C1 NTHIUKNPTBFSFZ-UHFFFAOYSA-N 0.000 claims description 2
- CEAYJLIWHKSKBI-UHFFFAOYSA-N [Li]C1CCC([Li])CC1 Chemical compound [Li]C1CCC([Li])CC1 CEAYJLIWHKSKBI-UHFFFAOYSA-N 0.000 claims description 2
- NTVIBFNHMURTMP-UHFFFAOYSA-N [Li]CC=CC[Li] Chemical compound [Li]CC=CC[Li] NTVIBFNHMURTMP-UHFFFAOYSA-N 0.000 claims description 2
- LKSSGADQJSOVHJ-UHFFFAOYSA-N [Li]CCC([Li])CC([Li])CCC([Li])CC Chemical compound [Li]CCC([Li])CC([Li])CCC([Li])CC LKSSGADQJSOVHJ-UHFFFAOYSA-N 0.000 claims description 2
- CYDIPADNXIGHGM-UHFFFAOYSA-N [Li]CCC([Li])CC[Li] Chemical compound [Li]CCC([Li])CC[Li] CYDIPADNXIGHGM-UHFFFAOYSA-N 0.000 claims description 2
- XJPQDUFPQWLTMJ-UHFFFAOYSA-N [Li]CCC=CCCCC([Li])CC Chemical compound [Li]CCC=CCCCC([Li])CC XJPQDUFPQWLTMJ-UHFFFAOYSA-N 0.000 claims description 2
- GRHMSLMCDLEHPK-UHFFFAOYSA-N [Li]CCCCCCCCCCC([Li])CCCCC([Li])CCCC[Li] Chemical compound [Li]CCCCCCCCCCC([Li])CCCCC([Li])CCCC[Li] GRHMSLMCDLEHPK-UHFFFAOYSA-N 0.000 claims description 2
- FNRUENJVQDCBQZ-UHFFFAOYSA-N [Li]CCCCCCCCCCCCCCCCCCCC[Li] Chemical compound [Li]CCCCCCCCCCCCCCCCCCCC[Li] FNRUENJVQDCBQZ-UHFFFAOYSA-N 0.000 claims description 2
- BZEZSORUWZUMNU-UHFFFAOYSA-N [Li]CCCC[Li] Chemical compound [Li]CCCC[Li] BZEZSORUWZUMNU-UHFFFAOYSA-N 0.000 claims description 2
- RNUIRRIRPXUDDA-UHFFFAOYSA-N [Li]c1c2ccccc2c([Li])c2ccccc12 Chemical compound [Li]c1c2ccccc2c([Li])c2ccccc12 RNUIRRIRPXUDDA-UHFFFAOYSA-N 0.000 claims description 2
- OKIWDOKGIBLCLR-UHFFFAOYSA-N bis(phenylmethoxy)-dipropylsilane Chemical compound C=1C=CC=CC=1CO[Si](CCC)(CCC)OCC1=CC=CC=C1 OKIWDOKGIBLCLR-UHFFFAOYSA-N 0.000 claims description 2
- IMJGQTCMUZMLRZ-UHFFFAOYSA-N buta-1,3-dien-2-ylbenzene Chemical compound C=CC(=C)C1=CC=CC=C1 IMJGQTCMUZMLRZ-UHFFFAOYSA-N 0.000 claims description 2
- 150000005690 diesters Chemical class 0.000 claims description 2
- JJQZDUKDJDQPMQ-UHFFFAOYSA-N dimethoxy(dimethyl)silane Chemical group CO[Si](C)(C)OC JJQZDUKDJDQPMQ-UHFFFAOYSA-N 0.000 claims description 2
- SCPWMSBAGXEGPW-UHFFFAOYSA-N dodecyl(trimethoxy)silane Chemical compound CCCCCCCCCCCC[Si](OC)(OC)OC SCPWMSBAGXEGPW-UHFFFAOYSA-N 0.000 claims description 2
- 229910052732 germanium Inorganic materials 0.000 claims description 2
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 claims description 2
- WTTUTKBXMMXKBQ-UHFFFAOYSA-N lithium;stilbene Chemical compound C=1C=CC=CC=1C([Li])C([Li])C1=CC=CC=C1 WTTUTKBXMMXKBQ-UHFFFAOYSA-N 0.000 claims description 2
- DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 claims description 2
- PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Natural products CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 claims description 2
- JCVQKRGIASEUKR-UHFFFAOYSA-N triethoxy(phenyl)silane Chemical compound CCO[Si](OCC)(OCC)C1=CC=CC=C1 JCVQKRGIASEUKR-UHFFFAOYSA-N 0.000 claims description 2
- AKYUXYJGXHZKLL-UHFFFAOYSA-N triethoxy(triethoxysilyl)silane Chemical group CCO[Si](OCC)(OCC)[Si](OCC)(OCC)OCC AKYUXYJGXHZKLL-UHFFFAOYSA-N 0.000 claims description 2
- PADYPAQRESYCQZ-UHFFFAOYSA-N triethoxy-(4-methylphenyl)silane Chemical compound CCO[Si](OCC)(OCC)C1=CC=C(C)C=C1 PADYPAQRESYCQZ-UHFFFAOYSA-N 0.000 claims description 2
- GYTROFMCUJZKNA-UHFFFAOYSA-N triethyl triethoxysilyl silicate Chemical group CCO[Si](OCC)(OCC)O[Si](OCC)(OCC)OCC GYTROFMCUJZKNA-UHFFFAOYSA-N 0.000 claims description 2
- PZPGRFITIJYNEJ-UHFFFAOYSA-N disilane Chemical compound [SiH3][SiH3] PZPGRFITIJYNEJ-UHFFFAOYSA-N 0.000 claims 3
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical compound [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 claims 3
- WHKQKJYDBPVOLB-UHFFFAOYSA-N 1-ethenylnaphthalene;2-ethenylnaphthalene Chemical compound C1=CC=CC2=CC(C=C)=CC=C21.C1=CC=C2C(C=C)=CC=CC2=C1 WHKQKJYDBPVOLB-UHFFFAOYSA-N 0.000 claims 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims 1
- ZEDXYOJKIFJKHK-UHFFFAOYSA-N [Li]CCCCC1=CC=CC=C1 Chemical compound [Li]CCCCC1=CC=CC=C1 ZEDXYOJKIFJKHK-UHFFFAOYSA-N 0.000 claims 1
- QWFRFVPEFDDMQD-UHFFFAOYSA-N [Li]CCCCCCCCCC[Li] Chemical compound [Li]CCCCCCCCCC[Li] QWFRFVPEFDDMQD-UHFFFAOYSA-N 0.000 claims 1
- ATGKAFZFOALBOF-UHFFFAOYSA-N cyclohexyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)C1CCCCC1 ATGKAFZFOALBOF-UHFFFAOYSA-N 0.000 claims 1
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 claims 1
- 230000000379 polymerizing effect Effects 0.000 claims 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims 1
- 229920000642 polymer Polymers 0.000 description 23
- 229920001971 elastomer Polymers 0.000 description 20
- 239000005060 rubber Substances 0.000 description 16
- 230000008878 coupling Effects 0.000 description 15
- 238000010168 coupling process Methods 0.000 description 15
- 238000005859 coupling reaction Methods 0.000 description 15
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical class CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 10
- 159000000001 potassium salts Chemical class 0.000 description 8
- 239000000047 product Substances 0.000 description 7
- 239000007822 coupling agent Substances 0.000 description 6
- 229940116441 divinylbenzene Drugs 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 239000000654 additive Substances 0.000 description 5
- 230000000996 additive effect Effects 0.000 description 4
- 235000019441 ethanol Nutrition 0.000 description 4
- 239000004615 ingredient Substances 0.000 description 4
- 239000011591 potassium Substances 0.000 description 4
- 238000012545 processing Methods 0.000 description 4
- MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical class CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 3
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical class CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000003963 antioxidant agent Substances 0.000 description 3
- 230000003078 antioxidant effect Effects 0.000 description 3
- 238000013329 compounding Methods 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 235000019198 oils Nutrition 0.000 description 3
- 150000003463 sulfur Chemical class 0.000 description 3
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- 229920002554 vinyl polymer Polymers 0.000 description 3
- 239000003039 volatile agent Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- DQFAIOJURQGXBT-UHFFFAOYSA-N 1,2,4-tris(ethenyl)benzene Chemical compound C=CC1=CC=C(C=C)C(C=C)=C1 DQFAIOJURQGXBT-UHFFFAOYSA-N 0.000 description 2
- FWFAJEYKHANIJP-UHFFFAOYSA-N 1,3,5-tris(ethenyl)naphthalene Chemical compound C1=CC=C(C=C)C2=CC(C=C)=CC(C=C)=C21 FWFAJEYKHANIJP-UHFFFAOYSA-N 0.000 description 2
- TUDTVAXRTPHZAJ-UHFFFAOYSA-N 1,3-bis(ethenyl)naphthalene Chemical compound C1=CC=CC2=CC(C=C)=CC(C=C)=C21 TUDTVAXRTPHZAJ-UHFFFAOYSA-N 0.000 description 2
- SUNMBRGCANLOEG-UHFFFAOYSA-N 1,3-dichloroacetone Chemical compound ClCC(=O)CCl SUNMBRGCANLOEG-UHFFFAOYSA-N 0.000 description 2
- FTUDIUREWUBVKL-UHFFFAOYSA-N 1,8-bis(ethenyl)naphthalene Chemical compound C1=CC(C=C)=C2C(C=C)=CC=CC2=C1 FTUDIUREWUBVKL-UHFFFAOYSA-N 0.000 description 2
- JVXPEVSEOVECRV-UHFFFAOYSA-N 2,4-bis(ethenyl)-1-phenylbenzene Chemical group C=CC1=CC(C=C)=CC=C1C1=CC=CC=C1 JVXPEVSEOVECRV-UHFFFAOYSA-N 0.000 description 2
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- OPFTUNCRGUEPRZ-QLFBSQMISA-N Cyclohexane Natural products CC(=C)[C@@H]1CC[C@@](C)(C=C)[C@H](C(C)=C)C1 OPFTUNCRGUEPRZ-QLFBSQMISA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical class CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- 235000021355 Stearic acid Nutrition 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- IAQRGUVFOMOMEM-ARJAWSKDSA-N cis-but-2-ene Chemical compound C\C=C/C IAQRGUVFOMOMEM-ARJAWSKDSA-N 0.000 description 2
- 230000002844 continuous effect Effects 0.000 description 2
- JBDSSBMEKXHSJF-UHFFFAOYSA-N cyclopentanecarboxylic acid Chemical class OC(=O)C1CCCC1 JBDSSBMEKXHSJF-UHFFFAOYSA-N 0.000 description 2
- 238000010908 decantation Methods 0.000 description 2
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical class CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
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- IUJLOAKJZQBENM-UHFFFAOYSA-N n-(1,3-benzothiazol-2-ylsulfanyl)-2-methylpropan-2-amine Chemical compound C1=CC=C2SC(SNC(C)(C)C)=NC2=C1 IUJLOAKJZQBENM-UHFFFAOYSA-N 0.000 description 1
- VHGRZFUFHFADPY-UHFFFAOYSA-N n-(3,5-diethyloctyl)-3,5-diethyloctan-1-amine Chemical class CCCC(CC)CC(CC)CCNCCC(CC)CC(CC)CCC VHGRZFUFHFADPY-UHFFFAOYSA-N 0.000 description 1
- ROZPNEGZBIUWBX-UHFFFAOYSA-N n-[bis(diethylamino)phosphoryl]-n-ethylethanamine Chemical compound CCN(CC)P(=O)(N(CC)CC)N(CC)CC ROZPNEGZBIUWBX-UHFFFAOYSA-N 0.000 description 1
- WAQPJHNWYPETBC-UHFFFAOYSA-N n-bis(dipropylamino)phosphoryl-n-propylpropan-1-amine Chemical compound CCCN(CCC)P(=O)(N(CCC)CCC)N(CCC)CCC WAQPJHNWYPETBC-UHFFFAOYSA-N 0.000 description 1
- 229920003052 natural elastomer Polymers 0.000 description 1
- 229920001194 natural rubber Polymers 0.000 description 1
- 210000005036 nerve Anatomy 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229960002446 octanoic acid Drugs 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical class CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 229960002969 oleic acid Drugs 0.000 description 1
- 235000021313 oleic acid Nutrition 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical class O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000005086 pumping Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 229940079877 pyrogallol Drugs 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 239000012744 reinforcing agent Substances 0.000 description 1
- 150000003298 rubidium compounds Chemical class 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- AIFMYMZGQVTROK-UHFFFAOYSA-N silicon tetrabromide Chemical compound Br[Si](Br)(Br)Br AIFMYMZGQVTROK-UHFFFAOYSA-N 0.000 description 1
- JHGCXUUFRJCMON-UHFFFAOYSA-J silicon(4+);tetraiodide Chemical compound [Si+4].[I-].[I-].[I-].[I-] JHGCXUUFRJCMON-UHFFFAOYSA-J 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 229960004274 stearic acid Drugs 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 150000004763 sulfides Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229920003051 synthetic elastomer Polymers 0.000 description 1
- XKXIQBVKMABYQJ-UHFFFAOYSA-N tert-butyl hydrogen carbonate Chemical class CC(C)(C)OC(O)=O XKXIQBVKMABYQJ-UHFFFAOYSA-N 0.000 description 1
- WMXCDAVJEZZYLT-UHFFFAOYSA-N tert-butylthiol Chemical compound CC(C)(C)S WMXCDAVJEZZYLT-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- UFHILTCGAOPTOV-UHFFFAOYSA-N tetrakis(ethenyl)silane Chemical compound C=C[Si](C=C)(C=C)C=C UFHILTCGAOPTOV-UHFFFAOYSA-N 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- ZOYFEXPFPVDYIS-UHFFFAOYSA-N trichloro(ethyl)silane Chemical compound CC[Si](Cl)(Cl)Cl ZOYFEXPFPVDYIS-UHFFFAOYSA-N 0.000 description 1
- ZDHXKXAHOVTTAH-UHFFFAOYSA-N trichlorosilane Chemical compound Cl[SiH](Cl)Cl ZDHXKXAHOVTTAH-UHFFFAOYSA-N 0.000 description 1
- 239000005052 trichlorosilane Substances 0.000 description 1
- KXGOWZRHSOJOLF-UHFFFAOYSA-N triethyl benzene-1,3,5-tricarboxylate Chemical compound CCOC(=O)C1=CC(C(=O)OCC)=CC(C(=O)OCC)=C1 KXGOWZRHSOJOLF-UHFFFAOYSA-N 0.000 description 1
- 239000001069 triethyl citrate Substances 0.000 description 1
- VMYFZRTXGLUXMZ-UHFFFAOYSA-N triethyl citrate Natural products CCOC(=O)C(O)(C(=O)OCC)C(=O)OCC VMYFZRTXGLUXMZ-UHFFFAOYSA-N 0.000 description 1
- 235000013769 triethyl citrate Nutrition 0.000 description 1
- LPJGAKAQBFCVTJ-UHFFFAOYSA-N tris(2-decyl-3-ethylaziridin-1-yl)-sulfanylidene-$l^{5}-phosphane Chemical compound CCCCCCCCCCC1C(CC)N1P(=S)(N1C(C1CC)CCCCCCCCCC)N1C(CCCCCCCCCC)C1CC LPJGAKAQBFCVTJ-UHFFFAOYSA-N 0.000 description 1
- PKRKCDBTXBGLKV-UHFFFAOYSA-N tris(ethenyl)-methylsilane Chemical compound C=C[Si](C)(C=C)C=C PKRKCDBTXBGLKV-UHFFFAOYSA-N 0.000 description 1
- FUJPAQRDHMJPBB-UHFFFAOYSA-N tris(ethenyl)-phenylsilane Chemical compound C=C[Si](C=C)(C=C)C1=CC=CC=C1 FUJPAQRDHMJPBB-UHFFFAOYSA-N 0.000 description 1
- OZHUWVSXUOMDDU-UHFFFAOYSA-N tris(ethenyl)phosphane Chemical compound C=CP(C=C)C=C OZHUWVSXUOMDDU-UHFFFAOYSA-N 0.000 description 1
- VSRBKQFNFZQRBM-UHFFFAOYSA-N tuaminoheptane Chemical class CCCCCC(C)N VSRBKQFNFZQRBM-UHFFFAOYSA-N 0.000 description 1
- 229920006163 vinyl copolymer Polymers 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000011787 zinc oxide 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
- C08F236/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds
- C08F236/02—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds
- C08F236/04—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds conjugated
- C08F236/10—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds conjugated with vinyl-aromatic monomers
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)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/722,253 US4137391A (en) | 1976-09-10 | 1976-09-10 | Continuous solution polymerization of a conjugated diene with a monovinylaromatic compound using alkoxysilicon treating agents in the first reactor means of a reactor series |
| US722,253 | 1976-09-10 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1094743A true CA1094743A (en) | 1981-01-27 |
Family
ID=24901082
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA276,888A Expired CA1094743A (en) | 1976-09-10 | 1977-04-25 | Continuous solution polymerization of a conjugated diene with a monovinylaromatic compound using alkoxysilicon treating agents in the first reactor means of a reactor series |
Country Status (11)
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4311803A (en) * | 1979-05-01 | 1982-01-19 | Phillips Petroleum Company | Continuous solution polymerization process |
| US4379891A (en) * | 1981-06-15 | 1983-04-12 | Shell Oil Company | Multifunctional coupling agent |
| US5191021A (en) * | 1988-06-29 | 1993-03-02 | The Goodyear Tire & Rubber Company | Tire with tread containing styrene, isoprene, butadiene terpolymer rubber |
| US5047483A (en) * | 1988-06-29 | 1991-09-10 | The Goodyear Tire & Rubber Company | Pneumatic tire with tread of styrene, isoprene, butadiene rubber |
| US5254653A (en) * | 1989-12-28 | 1993-10-19 | The Goodyear Tire & Rubber Company | Terpolymer rubber of styrene, isoprene and butadiene |
| US5159020A (en) * | 1989-12-28 | 1992-10-27 | The Goodyear Tire & Rubber Company | Tire with tread comprising styrene, isoprene, butadiene terpolymer rubber |
| US5266649A (en) * | 1992-06-01 | 1993-11-30 | Shell Oil Company | Color stable coupled diene polymers and hot melt adhesives containing them |
| JP3319639B2 (ja) | 1992-12-24 | 2002-09-03 | 株式会社ブリヂストン | 共役ジエン系重合体の製造方法、スチレン−ブタジエン系重合体及びそのゴム組成物 |
| US5552493A (en) * | 1995-05-30 | 1996-09-03 | Shell Oil Company | Method for producing asymmetric radial polymers |
| TW580503B (en) * | 1997-09-10 | 2004-03-21 | Fmc Corp | Process for improving stability of living polymerization chain ends |
| US6493573B1 (en) * | 1999-10-28 | 2002-12-10 | Winchester Development Associates | Method and system for navigating a catheter probe in the presence of field-influencing objects |
| JP5097803B2 (ja) * | 2010-04-05 | 2012-12-12 | 住友ゴム工業株式会社 | タイヤ用ゴム組成物及び空気入りタイヤ |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3244664A (en) * | 1960-10-24 | 1966-04-05 | Phillips Petroleum Co | Silicon-containing polymers |
| US3198774A (en) * | 1961-11-14 | 1965-08-03 | Phillips Petroleum Co | Continuous process for the preparation of block copolymers |
| US3356763A (en) * | 1962-04-09 | 1967-12-05 | Phillips Petroleum Co | Continuous process for producing block copolymers of dienes and vinyl aromatic hydrocarbons |
| BE638995A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1962-07-16 | |||
| US3281383A (en) * | 1962-08-09 | 1966-10-25 | Phillips Petroleum Co | Branched polymers prepared from monolithium-terminated polymers and compounds having at least three reactive sites |
| US3297793A (en) * | 1962-12-21 | 1967-01-10 | Phillips Petroleum Co | Continuous process for producing block copolymers of dienes and vinyl aromatic compounds |
| US3294768A (en) * | 1963-11-14 | 1966-12-27 | Phillips Petroleum Co | Preparation of conjugated diene polymers |
| US3439064A (en) * | 1965-01-11 | 1969-04-15 | Exxon Research Engineering Co | Laminating varnish consisting of low viscosity,curable block copolymer |
| US3427264A (en) * | 1966-02-07 | 1969-02-11 | Exxon Research Engineering Co | Metal-filled plastics comprising a styrene polymer and an elastomer |
| US3681304A (en) * | 1970-07-29 | 1972-08-01 | Firestone Tire & Rubber Co | Process for the polymerization of conjugated dienes |
| BE788122A (fr) * | 1971-09-07 | 1973-02-28 | Phillips Petroleum Co | Composés lithiés multifonctionnels d'amorcage de polymérisation. |
| BE790972A (fr) * | 1971-11-04 | 1973-05-07 | Phillips Petroleum Co | Addition d'un agent de couplage durant des polymérisations amorcées par un composé organolithié |
| US3787377A (en) * | 1971-12-16 | 1974-01-22 | Firestone Tire & Rubber Co | Continuous process of copolymerizing butadiene and styrene |
| FR2295972A1 (fr) * | 1974-12-23 | 1976-07-23 | Michelin & Cie | Polymerisation ou copolymerisation en solution d'un ou plusieurs dienes conjugues avec eventuellement un ou plusieurs composes vinylaromatiques |
-
1976
- 1976-09-10 US US05/722,253 patent/US4137391A/en not_active Expired - Lifetime
-
1977
- 1977-04-25 CA CA276,888A patent/CA1094743A/en not_active Expired
- 1977-09-01 AU AU28470/77A patent/AU507329B2/en not_active Expired
- 1977-09-05 GB GB36975/77A patent/GB1586615A/en not_active Expired
- 1977-09-08 DE DE19772740496 patent/DE2740496A1/de not_active Ceased
- 1977-09-09 ES ES462246A patent/ES462246A1/es not_active Expired
- 1977-09-09 JP JP10872877A patent/JPS5335787A/ja active Granted
- 1977-09-09 MX MX170522A patent/MX145566A/es unknown
- 1977-09-09 FR FR7727406A patent/FR2364233A1/fr active Granted
- 1977-09-09 NL NL7709940.A patent/NL164294C/xx active
- 1977-09-12 BE BE180827A patent/BE858604A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BE858604A (fr) | 1978-03-13 |
| AU507329B2 (en) | 1980-02-14 |
| AU2847077A (en) | 1979-03-08 |
| DE2740496A1 (de) | 1978-03-16 |
| FR2364233B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1981-07-24 |
| NL7709940A (nl) | 1978-03-14 |
| JPS546274B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1979-03-27 |
| US4137391A (en) | 1979-01-30 |
| ES462246A1 (es) | 1978-06-01 |
| MX145566A (es) | 1982-03-08 |
| JPS5335787A (en) | 1978-04-03 |
| NL164294C (nl) | 1980-12-15 |
| GB1586615A (en) | 1981-03-25 |
| FR2364233A1 (fr) | 1978-04-07 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry | ||
| MKEX | Expiry |
Effective date: 19980127 |