CA2023218C - Process for the preparation of copolymers of conjugated dienes and vinyl aromatic compounds - Google Patents
Process for the preparation of copolymers of conjugated dienes and vinyl aromatic compounds Download PDFInfo
- Publication number
- CA2023218C CA2023218C CA002023218A CA2023218A CA2023218C CA 2023218 C CA2023218 C CA 2023218C CA 002023218 A CA002023218 A CA 002023218A CA 2023218 A CA2023218 A CA 2023218A CA 2023218 C CA2023218 C CA 2023218C
- Authority
- CA
- Canada
- Prior art keywords
- solvent
- weight
- copolymerization
- styrene
- cyclopentane
- 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 - Fee Related
Links
- 238000000034 method Methods 0.000 title claims abstract description 51
- -1 vinyl aromatic compounds Chemical class 0.000 title claims abstract description 28
- 229920002554 vinyl polymer Polymers 0.000 title claims abstract description 27
- 238000002360 preparation method Methods 0.000 title claims abstract description 14
- 229920001577 copolymer Polymers 0.000 title claims description 34
- 150000001993 dienes Chemical class 0.000 title abstract description 15
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims abstract description 54
- 239000002904 solvent Substances 0.000 claims abstract description 45
- 239000000178 monomer Substances 0.000 claims abstract description 36
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 claims abstract description 27
- 229920001400 block copolymer Polymers 0.000 claims abstract description 23
- 239000003999 initiator Substances 0.000 claims abstract description 23
- 238000006243 chemical reaction Methods 0.000 claims abstract description 21
- 229920005604 random copolymer Polymers 0.000 claims abstract description 14
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims abstract description 8
- 229910052744 lithium Inorganic materials 0.000 claims abstract description 8
- 238000001816 cooling Methods 0.000 claims abstract description 7
- 238000010992 reflux Methods 0.000 claims abstract description 5
- 239000012442 inert solvent Substances 0.000 claims abstract 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 58
- 238000006116 polymerization reaction Methods 0.000 claims description 48
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 44
- 239000000203 mixture Substances 0.000 claims description 41
- 238000007334 copolymerization reaction Methods 0.000 claims description 25
- 150000001875 compounds Chemical class 0.000 claims description 14
- QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 claims description 12
- 239000011541 reaction mixture Substances 0.000 claims description 7
- 125000001931 aliphatic group Chemical group 0.000 claims description 6
- AFABGHUZZDYHJO-UHFFFAOYSA-N dimethyl butane Natural products CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 claims description 6
- 150000001491 aromatic compounds Chemical class 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 229920000468 styrene butadiene styrene block copolymer Polymers 0.000 claims description 2
- 239000002174 Styrene-butadiene Substances 0.000 claims 1
- FACXGONDLDSNOE-UHFFFAOYSA-N buta-1,3-diene;styrene Chemical compound C=CC=C.C=CC1=CC=CC=C1.C=CC1=CC=CC=C1 FACXGONDLDSNOE-UHFFFAOYSA-N 0.000 claims 1
- MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical compound C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 claims 1
- 229920006030 multiblock copolymer Polymers 0.000 claims 1
- 239000011115 styrene butadiene Substances 0.000 claims 1
- 229920003048 styrene butadiene rubber Polymers 0.000 claims 1
- 229920000428 triblock copolymer Polymers 0.000 claims 1
- 238000005859 coupling reaction Methods 0.000 description 36
- 238000010168 coupling process Methods 0.000 description 31
- 230000008878 coupling Effects 0.000 description 30
- 229920000642 polymer Polymers 0.000 description 20
- WGOPGODQLGJZGL-UHFFFAOYSA-N lithium;butane Chemical compound [Li+].CC[CH-]C WGOPGODQLGJZGL-UHFFFAOYSA-N 0.000 description 17
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 16
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 15
- VIZORQUEIQEFRT-UHFFFAOYSA-N Diethyl adipate Chemical compound CCOC(=O)CCCCC(=O)OCC VIZORQUEIQEFRT-UHFFFAOYSA-N 0.000 description 10
- 239000003085 diluting agent Substances 0.000 description 10
- 239000003795 chemical substances by application Substances 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 8
- 239000004793 Polystyrene Substances 0.000 description 7
- 238000009826 distribution Methods 0.000 description 7
- 229920002223 polystyrene Polymers 0.000 description 7
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 6
- 239000007822 coupling agent Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 238000004073 vulcanization Methods 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 206010011878 Deafness Diseases 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000004568 cement Substances 0.000 description 3
- 238000011084 recovery Methods 0.000 description 3
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- SDJHPPZKZZWAKF-UHFFFAOYSA-N 2,3-dimethylbuta-1,3-diene Chemical compound CC(=C)C(C)=C SDJHPPZKZZWAKF-UHFFFAOYSA-N 0.000 description 2
- RCJMVGJKROQDCB-UHFFFAOYSA-N 2-methylpenta-1,3-diene Chemical compound CC=CC(C)=C RCJMVGJKROQDCB-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 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 description 2
- CEKMWTQZICDDCU-UHFFFAOYSA-N [Li]CC[Li] Chemical compound [Li]CC[Li] CEKMWTQZICDDCU-UHFFFAOYSA-N 0.000 description 2
- PDNLMVORQDXJOD-UHFFFAOYSA-N [Li]C[Li] Chemical compound [Li]C[Li] PDNLMVORQDXJOD-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000003213 activating effect Effects 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 238000012661 block copolymerization Methods 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 230000015271 coagulation Effects 0.000 description 2
- 238000005345 coagulation Methods 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 238000000265 homogenisation Methods 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- WDDLHZXDSVMNRK-UHFFFAOYSA-N lithium;3-methanidylheptane Chemical compound [Li+].CCCCC([CH2-])CC WDDLHZXDSVMNRK-UHFFFAOYSA-N 0.000 description 2
- SZAVVKVUMPLRRS-UHFFFAOYSA-N lithium;propane Chemical compound [Li+].C[CH-]C SZAVVKVUMPLRRS-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 description 2
- 239000002574 poison Substances 0.000 description 2
- 231100000614 poison Toxicity 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000005049 silicon tetrachloride Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- PCCCQOGUVCNYOI-FNORWQNLSA-N (3e)-2,3-dimethylpenta-1,3-diene Chemical compound C\C=C(/C)C(C)=C PCCCQOGUVCNYOI-FNORWQNLSA-N 0.000 description 1
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical compound C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 description 1
- APQIUTYORBAGEZ-UHFFFAOYSA-N 1,1-dibromoethane Chemical compound CC(Br)Br APQIUTYORBAGEZ-UHFFFAOYSA-N 0.000 description 1
- 238000011925 1,2-addition Methods 0.000 description 1
- CORMBJOFDGICKF-UHFFFAOYSA-N 1,3,5-trimethoxy 2-vinyl benzene Natural products COC1=CC(OC)=C(C=C)C(OC)=C1 CORMBJOFDGICKF-UHFFFAOYSA-N 0.000 description 1
- HVOKBODBWQEEGI-UHFFFAOYSA-N 1-ethenyl-3,5-diethylbenzene Chemical compound CCC1=CC(CC)=CC(C=C)=C1 HVOKBODBWQEEGI-UHFFFAOYSA-N 0.000 description 1
- XSHXURIGVYRXAD-UHFFFAOYSA-N 1-ethenyl-3,5-diphenylbenzene Chemical compound C=1C(C=C)=CC(C=2C=CC=CC=2)=CC=1C1=CC=CC=C1 XSHXURIGVYRXAD-UHFFFAOYSA-N 0.000 description 1
- VVTGQMLRTKFKAM-UHFFFAOYSA-N 1-ethenyl-4-propylbenzene Chemical compound CCCC1=CC=C(C=C)C=C1 VVTGQMLRTKFKAM-UHFFFAOYSA-N 0.000 description 1
- IGGDKDTUCAWDAN-UHFFFAOYSA-N 1-vinylnaphthalene Chemical compound C1=CC=C2C(C=C)=CC=CC2=C1 IGGDKDTUCAWDAN-UHFFFAOYSA-N 0.000 description 1
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 1
- PDELBHCVXBSVPJ-UHFFFAOYSA-N 2-ethenyl-1,3,5-trimethylbenzene Chemical compound CC1=CC(C)=C(C=C)C(C)=C1 PDELBHCVXBSVPJ-UHFFFAOYSA-N 0.000 description 1
- MHKLKWCYGIBEQF-UHFFFAOYSA-N 4-(1,3-benzothiazol-2-ylsulfanyl)morpholine Chemical compound C1COCCN1SC1=NC2=CC=CC=C2S1 MHKLKWCYGIBEQF-UHFFFAOYSA-N 0.000 description 1
- HLBZWYXLQJQBKU-UHFFFAOYSA-N 4-(morpholin-4-yldisulfanyl)morpholine Chemical compound C1COCCN1SSN1CCOCC1 HLBZWYXLQJQBKU-UHFFFAOYSA-N 0.000 description 1
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 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 1
- AQUURBLHMACBRN-UHFFFAOYSA-N C1(=CC=CC=C1)C=1C=CC=C2C=CC=C(C12)C=C.C(C)C=1C=C(C2=CC=CC=C2C1)C=C Chemical compound C1(=CC=CC=C1)C=1C=CC=C2C=CC=C(C12)C=C.C(C)C=1C=C(C2=CC=CC=C2C1)C=C AQUURBLHMACBRN-UHFFFAOYSA-N 0.000 description 1
- WKNIPOZMZRSXGI-UHFFFAOYSA-N C1=CC=C2C([Li])=CC=CC2=C1[Li] Chemical compound C1=CC=C2C([Li])=CC=CC2=C1[Li] WKNIPOZMZRSXGI-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- UDSFAEKRVUSQDD-UHFFFAOYSA-N Dimethyl adipate Chemical compound COC(=O)CCCCC(=O)OC UDSFAEKRVUSQDD-UHFFFAOYSA-N 0.000 description 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
- 239000004606 Fillers/Extenders Substances 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
- 244000046052 Phaseolus vulgaris Species 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000005864 Sulphur Substances 0.000 description 1
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- VOTZHAZMXFYESM-UHFFFAOYSA-N [Li]C1=CC=CC([Li])=C1 Chemical compound [Li]C1=CC=CC([Li])=C1 VOTZHAZMXFYESM-UHFFFAOYSA-N 0.000 description 1
- QQDSVXYDUMVTSQ-UHFFFAOYSA-N [Li]CCCCC[Li] Chemical compound [Li]CCCCC[Li] QQDSVXYDUMVTSQ-UHFFFAOYSA-N 0.000 description 1
- TVKQVMQEOOKKMN-UHFFFAOYSA-N [Li]CCC[Li] Chemical compound [Li]CCC[Li] TVKQVMQEOOKKMN-UHFFFAOYSA-N 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000010539 anionic addition polymerization reaction Methods 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 229910052570 clay Inorganic materials 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- 125000005442 diisocyanate group Chemical group 0.000 description 1
- 238000010981 drying operation Methods 0.000 description 1
- 210000005069 ears Anatomy 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 229940093499 ethyl acetate Drugs 0.000 description 1
- 235000019439 ethyl acetate Nutrition 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 239000011256 inorganic filler Substances 0.000 description 1
- 229910003475 inorganic filler Inorganic materials 0.000 description 1
- 230000002452 interceptive effect Effects 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 150000002642 lithium compounds Chemical class 0.000 description 1
- 235000015250 liver sausages Nutrition 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000001979 organolithium group Chemical group 0.000 description 1
- HDBWAWNLGGMZRQ-UHFFFAOYSA-N p-Vinylbiphenyl Chemical compound C1=CC(C=C)=CC=C1C1=CC=CC=C1 HDBWAWNLGGMZRQ-UHFFFAOYSA-N 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- FCJSHPDYVMKCHI-UHFFFAOYSA-N phenyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OC1=CC=CC=C1 FCJSHPDYVMKCHI-UHFFFAOYSA-N 0.000 description 1
- PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Natural products CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 description 1
- 239000011414 polymer cement Substances 0.000 description 1
- 229920000346 polystyrene-polyisoprene block-polystyrene Polymers 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 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
- C08F297/00—Macromolecular compounds obtained by successively polymerising different monomer systems using a catalyst of the ionic or coordination type without deactivating the intermediate polymer
- C08F297/02—Macromolecular compounds obtained by successively polymerising different monomer systems using a catalyst of the ionic or coordination type without deactivating the intermediate polymer using a catalyst of the anionic type
- C08F297/04—Macromolecular compounds obtained by successively polymerising different monomer systems using a catalyst of the ionic or coordination type without deactivating the intermediate polymer using a catalyst of the anionic type polymerising vinyl aromatic monomers and conjugated dienes
-
- 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)
- Inorganic Chemistry (AREA)
- Graft Or Block Polymers (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 |
|---|---|---|---|
| GB8918702.5 | 1989-08-16 | ||
| GB898918702A GB8918702D0 (en) | 1989-08-16 | 1989-08-16 | Process for the preparation of random solution copolymers of conjugated dienes and vinyl aromatic compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2023218A1 CA2023218A1 (en) | 1991-02-17 |
| CA2023218C true CA2023218C (en) | 2001-02-20 |
Family
ID=10661721
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002023218A Expired - Fee Related CA2023218C (en) | 1989-08-16 | 1990-08-14 | Process for the preparation of copolymers of conjugated dienes and vinyl aromatic compounds |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US5336737A (en:Method) |
| EP (1) | EP0413403B1 (en:Method) |
| JP (1) | JP3281366B2 (en:Method) |
| CA (1) | CA2023218C (en:Method) |
| DE (1) | DE69033196T2 (en:Method) |
| GB (1) | GB8918702D0 (en:Method) |
| IN (1) | IN180176B (en:Method) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6313216B1 (en) * | 2000-09-01 | 2001-11-06 | The Goodyear Tire & Rubber Company | Synthesis of styrene-isoprene rubber |
| US6759454B2 (en) * | 2002-02-07 | 2004-07-06 | Kraton Polymers U.S. Llc | Polymer modified bitumen compositions |
| US20030181584A1 (en) * | 2002-02-07 | 2003-09-25 | Kraton Polymers U.S. Llc | Elastomeric articles prepared from controlled distribution block copolymers |
| JP2007506842A (ja) | 2003-09-23 | 2007-03-22 | デイス−アナリティック コーポレーション | 新規なブロックコポリマー及びその製造方法 |
| US7737218B2 (en) * | 2006-12-29 | 2010-06-15 | Bridgestone Corporation | Method for generating free radical capable polymers using tin or silicon halide compounds |
| US8030410B2 (en) * | 2006-12-29 | 2011-10-04 | Bridgestone Corporation | Method for generating free radical capable polymers using carbonyl-containing compounds |
| JP5037174B2 (ja) * | 2007-03-02 | 2012-09-26 | 日本曹達株式会社 | 共役ジエン系スターポリマー及びその製造方法 |
| CN102272176A (zh) * | 2008-12-02 | 2011-12-07 | 雅宝公司 | 支化和星形支化的苯乙烯聚合物、调聚物和加合物，其合成、其溴化及其用途 |
| WO2011132395A1 (ja) * | 2010-04-21 | 2011-10-27 | 日本曹達株式会社 | スターポリマー及びその製法 |
| US8946365B2 (en) | 2012-01-18 | 2015-02-03 | Eastman Chemical Company | Low molecular weight polystyrene resin and methods of making and using the same |
| US9127132B2 (en) | 2013-10-08 | 2015-09-08 | Katon Polymers U.S. LLC | Process for coagulating sulfonated block copolymers |
| CN104628918B (zh) * | 2013-11-12 | 2017-07-25 | 中国石油化工股份有限公司 | 一种共轭二烯烃聚合物及其制备方法 |
| KR102518564B1 (ko) | 2014-09-04 | 2023-04-05 | 주식회사 쿠라레 | 아니온 중합체의 제조 방법 |
Family Cites Families (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE637376A (en:Method) * | 1958-05-23 | |||
| US3294768A (en) * | 1963-11-14 | 1966-12-27 | Phillips Petroleum Co | Preparation of conjugated diene polymers |
| GB1066667A (en) * | 1964-06-08 | 1967-04-26 | Phillips Petroleum Co | Preparation of random copolymers |
| US3390207A (en) * | 1964-10-28 | 1968-06-25 | Shell Oil Co | Method of making block copolymers of dienes and vinyl aryl compounds |
| NL135608C (en:Method) * | 1966-11-28 | |||
| GB1146450A (en) * | 1966-12-09 | 1969-03-26 | Asahi Chemical Ind | Process for producing random copolymers |
| ES368488A1 (es) * | 1968-06-20 | 1971-05-01 | Shell Int Research | Procedimiento para preparar copolimeros al azar de estirenoy butadieno. |
| NL145567B (nl) * | 1970-04-16 | 1975-04-15 | Shell Int Research | Werkwijze voor de niet-continue copolymerisatie van geconjugeerde dienen met ten hoogste 5 c-atomen en vinylaromatische verbindingen. |
| NL164050C (nl) * | 1972-05-31 | 1980-11-17 | Shell Int Research | Werkwijze voor het bereiden van polymeren met een verbrede molecuulgewichtsdistributie uit levende homo- of copolymeren van geconjugeerde dienen. |
| GB1400497A (en) * | 1972-08-01 | 1975-07-16 | Shell Int Research | Polymerisation of conjugated dienes |
| CH562098A5 (en:Method) * | 1973-02-27 | 1975-05-30 | Steiger Engineering Ag | |
| US3953543A (en) * | 1973-12-26 | 1976-04-27 | The Firestone Tire & Rubber Company | Polymerization process and polymer produced thereby |
| DE2504659C3 (de) * | 1975-02-05 | 1988-02-11 | Hüls AG, 4370 Marl | Verfahren zum geregelten Abführen der Reaktionswärme bei Polymerisationsreaktionen in Dispersion bzw. Lösung |
| GB2071117B (en) * | 1980-03-07 | 1984-05-10 | Dunlop Ltd | Elastomers and tyres containing them |
| US4358401A (en) * | 1980-03-31 | 1982-11-09 | New England Nuclear Corporation | Liquid emulsion scintillators which solidify for facile disposal |
| JPS57100112A (en) * | 1980-12-16 | 1982-06-22 | Asahi Chem Ind Co Ltd | Perfectly random styrene-butadiene copolymer rubber |
| GB8316052D0 (en) * | 1983-06-13 | 1983-07-20 | Shell Int Research | Elastomeric copolymers |
| GB8407629D0 (en) * | 1984-03-23 | 1984-05-02 | Shell Int Research | Preparation of polymers |
| GB2200123B (en) * | 1986-12-02 | 1990-06-13 | Shell Int Research | Elastomers and tyres containing them |
| GB8724437D0 (en) * | 1987-10-19 | 1987-11-25 | Shell Int Research | Elastomeric compositions |
-
1989
- 1989-08-16 GB GB898918702A patent/GB8918702D0/en active Pending
-
1990
- 1990-08-13 IN IN813DE1990 patent/IN180176B/en unknown
- 1990-08-14 CA CA002023218A patent/CA2023218C/en not_active Expired - Fee Related
- 1990-08-14 JP JP21488690A patent/JP3281366B2/ja not_active Expired - Fee Related
- 1990-08-15 DE DE69033196T patent/DE69033196T2/de not_active Expired - Fee Related
- 1990-08-15 EP EP90202213A patent/EP0413403B1/en not_active Expired - Lifetime
- 1990-08-15 US US07/567,843 patent/US5336737A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| EP0413403A1 (en) | 1991-02-20 |
| IN180176B (en:Method) | 1998-01-17 |
| DE69033196D1 (de) | 1999-08-12 |
| US5336737A (en) | 1994-08-09 |
| EP0413403B1 (en) | 1999-07-07 |
| GB8918702D0 (en) | 1989-09-27 |
| JP3281366B2 (ja) | 2002-05-13 |
| JPH0388803A (ja) | 1991-04-15 |
| CA2023218A1 (en) | 1991-02-17 |
| DE69033196T2 (de) | 2000-01-27 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| AU605370B2 (en) | Elastomeric compositions, process for the preparation thereof and tyres containing them | |
| JP2628822B2 (ja) | 連続漸減ポリマー類およびコポリマー類の製造方法およびそれを用いて製造した製品 | |
| CA2023218C (en) | Process for the preparation of copolymers of conjugated dienes and vinyl aromatic compounds | |
| US5891947A (en) | In-situ anionic continuous dispersion polymerization process | |
| CN101563398B (zh) | 支化聚合物及其合成和使用方法 | |
| EP0691991A1 (en) | METHOD FOR PRODUCING A BLOCK COPOLYMER COMPOSITION AND BLOCK COPOLYMER COMPOSITION | |
| CN109206568B (zh) | 一种含1,2结构均匀分布丁二烯嵌段的sbs及其氢化物和制备及应用方法 | |
| JP2005509066A (ja) | 線状のブロック共重合体及びその製造方法 | |
| CA1335468C (en) | Process for the preparation of polymers based on conjugated dienes and optionally monovinylaromatic compounds | |
| CN108235707A (zh) | 沥青改性剂和包含该沥青改性剂的沥青组合物 | |
| US3560593A (en) | Production of block copolymers | |
| EP3143057B1 (en) | Branched broad mwd conjugated diene polymer | |
| CN109415457A (zh) | 制备官能化聚合物的方法 | |
| JP3877836B2 (ja) | テトラヒドロピラニルメタノールのアルキルエーテルの存在下での共役ジエンとビニルアレーンのアニオン共重合 | |
| US5061758A (en) | Unsaturated, elastomeric, asymmetrically, coupled block copolymers, a dual batch process for its manufacture and their use for the production of type components | |
| JPH0345098B2 (en:Method) | ||
| US4232137A (en) | Cooling an alpha-methylstyrene polymerization mass | |
| CN109749011B (zh) | 三元无规共聚物和三元无规共聚物组合物及其应用以及阴离子聚合方法 | |
| CN103214621A (zh) | 立构规整共轭二烯烃/苯乙烯共聚物及其制备方法 | |
| JPS63297410A (ja) | スチレン・ブタジエン共重合体の製造方法 | |
| CN109749010B (zh) | 无规共聚物和无规共聚物组合物及其应用以及阴离子聚合方法 | |
| US3734898A (en) | Process for the preparing of random copolymers of conjugated dienes and vinyl aromatic hydrocarbons | |
| CN113956412A (zh) | 氢化苯乙烯类热塑性弹性体及其制备方法 | |
| US4102849A (en) | Oil-extended hydrogenated diblock copolymer | |
| CN114539492B (zh) | 单乙烯基芳烃-共轭二烯烃嵌段共聚物及其制备方法和充油橡胶及应用 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |