JP2013544303A - シラン含有カルビノール末端化ポリマー - Google Patents
シラン含有カルビノール末端化ポリマー Download PDFInfo
- Publication number
- JP2013544303A JP2013544303A JP2013539207A JP2013539207A JP2013544303A JP 2013544303 A JP2013544303 A JP 2013544303A JP 2013539207 A JP2013539207 A JP 2013539207A JP 2013539207 A JP2013539207 A JP 2013539207A JP 2013544303 A JP2013544303 A JP 2013544303A
- Authority
- JP
- Japan
- Prior art keywords
- polymer
- group
- functionalized
- end groups
- oxa
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 229920000642 polymer Polymers 0.000 title claims abstract description 56
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 title claims abstract description 14
- 229910000077 silane Inorganic materials 0.000 title claims abstract description 14
- 229910052710 silicon Inorganic materials 0.000 claims abstract description 21
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 20
- 125000003118 aryl group Chemical group 0.000 claims abstract description 19
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 14
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 14
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 14
- 125000002877 alkyl aryl group Chemical group 0.000 claims abstract description 7
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 7
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 7
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 7
- 125000000962 organic group Chemical group 0.000 claims abstract description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 3
- 229920001971 elastomer Polymers 0.000 claims description 62
- 239000005060 rubber Substances 0.000 claims description 61
- 239000000203 mixture Substances 0.000 claims description 38
- 238000000034 method Methods 0.000 claims description 30
- 239000000945 filler Substances 0.000 claims description 21
- 239000003921 oil Substances 0.000 claims description 20
- 238000006116 polymerization reaction Methods 0.000 claims description 15
- 230000008569 process Effects 0.000 claims description 15
- 150000001875 compounds Chemical class 0.000 claims description 14
- 229920002554 vinyl polymer Polymers 0.000 claims description 11
- 230000009477 glass transition Effects 0.000 claims description 9
- 239000000178 monomer Substances 0.000 claims description 9
- 239000000376 reactant Substances 0.000 claims description 9
- 229920013730 reactive polymer Polymers 0.000 claims description 9
- 239000003153 chemical reaction reagent Substances 0.000 claims description 8
- 229920001577 copolymer Polymers 0.000 claims description 8
- 239000005062 Polybutadiene Substances 0.000 claims description 7
- 238000013016 damping Methods 0.000 claims description 7
- 150000001993 dienes Chemical class 0.000 claims description 7
- 229920002857 polybutadiene Polymers 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 229910052751 metal Inorganic materials 0.000 claims description 6
- 239000002184 metal Substances 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 239000007822 coupling agent Substances 0.000 claims description 5
- 229910052779 Neodymium Inorganic materials 0.000 claims description 4
- 229910052744 lithium Inorganic materials 0.000 claims description 4
- 229910052759 nickel Inorganic materials 0.000 claims description 4
- 229910052719 titanium Inorganic materials 0.000 claims description 4
- 229910052782 aluminium Inorganic materials 0.000 claims description 3
- 239000003963 antioxidant agent Substances 0.000 claims description 3
- 229910052742 iron Inorganic materials 0.000 claims description 3
- 229910052700 potassium Inorganic materials 0.000 claims description 3
- 229910052708 sodium Inorganic materials 0.000 claims description 3
- 241001441571 Hiodontidae Species 0.000 claims description 2
- 230000005540 biological transmission Effects 0.000 claims description 2
- 229910052791 calcium Inorganic materials 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 238000007334 copolymerization reaction Methods 0.000 claims description 2
- 229910052749 magnesium Inorganic materials 0.000 claims description 2
- 229920001195 polyisoprene Polymers 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 238000007789 sealing Methods 0.000 claims description 2
- 230000003078 antioxidant effect Effects 0.000 claims 1
- RTACIUYXLGWTAE-UHFFFAOYSA-N buta-1,3-diene;2-methylbuta-1,3-diene;styrene Chemical compound C=CC=C.CC(=C)C=C.C=CC1=CC=CC=C1 RTACIUYXLGWTAE-UHFFFAOYSA-N 0.000 claims 1
- 125000002897 diene group Chemical group 0.000 claims 1
- 229910052752 metalloid Inorganic materials 0.000 claims 1
- 150000002738 metalloids Chemical class 0.000 claims 1
- 238000000465 moulding Methods 0.000 claims 1
- 229920001897 terpolymer Polymers 0.000 claims 1
- 229910052718 tin Inorganic materials 0.000 claims 1
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 24
- 239000002904 solvent Substances 0.000 description 17
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 13
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 13
- 239000000284 extract Substances 0.000 description 12
- -1 4-butylphenyllithium Chemical compound 0.000 description 11
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 10
- 239000006229 carbon black Substances 0.000 description 10
- 238000005096 rolling process Methods 0.000 description 10
- 239000000243 solution Substances 0.000 description 9
- 229920003048 styrene butadiene rubber Polymers 0.000 description 9
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 8
- 238000005859 coupling reaction Methods 0.000 description 7
- 238000004566 IR spectroscopy Methods 0.000 description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 6
- 230000008878 coupling Effects 0.000 description 6
- 238000010168 coupling process Methods 0.000 description 6
- 239000011593 sulfur Substances 0.000 description 6
- 229920006318 anionic polymer Polymers 0.000 description 5
- 230000008901 benefit Effects 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 239000000377 silicon dioxide Substances 0.000 description 5
- 238000004073 vulcanization Methods 0.000 description 5
- FZLHAQMQWDDWFI-UHFFFAOYSA-N 2-[2-(oxolan-2-yl)propan-2-yl]oxolane Chemical compound C1CCOC1C(C)(C)C1CCCO1 FZLHAQMQWDDWFI-UHFFFAOYSA-N 0.000 description 4
- 239000004606 Fillers/Extenders Substances 0.000 description 4
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 4
- 229910002808 Si–O–Si Inorganic materials 0.000 description 4
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 4
- 238000007306 functionalization reaction Methods 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 239000003505 polymerization initiator Substances 0.000 description 4
- 150000004756 silanes Chemical class 0.000 description 4
- 238000003860 storage Methods 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- 229920000459 Nitrile rubber Polymers 0.000 description 3
- 229910008051 Si-OH Inorganic materials 0.000 description 3
- 229910006358 Si—OH Inorganic materials 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000000129 anionic group Chemical group 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- 239000012967 coordination catalyst Substances 0.000 description 3
- 238000007730 finishing process Methods 0.000 description 3
- 229910044991 metal oxide Inorganic materials 0.000 description 3
- 150000004706 metal oxides Chemical class 0.000 description 3
- 230000000704 physical effect Effects 0.000 description 3
- 239000002685 polymerization catalyst Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000005987 sulfurization reaction Methods 0.000 description 3
- 238000003786 synthesis reaction 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
- KVNYFPKFSJIPBJ-UHFFFAOYSA-N 1,2-diethylbenzene Chemical compound CCC1=CC=CC=C1CC KVNYFPKFSJIPBJ-UHFFFAOYSA-N 0.000 description 2
- QRMPKOFEUHIBNM-UHFFFAOYSA-N 1,4-dimethylcyclohexane Chemical compound CC1CCC(C)CC1 QRMPKOFEUHIBNM-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
- VVBLNCFGVYUYGU-UHFFFAOYSA-N 4,4'-Bis(dimethylamino)benzophenone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)C1=CC=C(N(C)C)C=C1 VVBLNCFGVYUYGU-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- 229920002943 EPDM rubber Polymers 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- 244000043261 Hevea brasiliensis Species 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical class CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- 239000006057 Non-nutritive feed additive Substances 0.000 description 2
- 229920006978 SSBR Polymers 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
- 150000001298 alcohols Chemical class 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000011109 contamination Methods 0.000 description 2
- 230000001419 dependent effect Effects 0.000 description 2
- 229920003244 diene elastomer Polymers 0.000 description 2
- IIEWJVIFRVWJOD-UHFFFAOYSA-N ethylcyclohexane Chemical compound CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 239000003365 glass fiber Substances 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- AFRJJFRNGGLMDW-UHFFFAOYSA-N lithium amide Chemical class [Li+].[NH2-] AFRJJFRNGGLMDW-UHFFFAOYSA-N 0.000 description 2
- WGOPGODQLGJZGL-UHFFFAOYSA-N lithium;butane Chemical compound [Li+].CC[CH-]C WGOPGODQLGJZGL-UHFFFAOYSA-N 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
- 229920003052 natural elastomer Polymers 0.000 description 2
- 229920001194 natural rubber Polymers 0.000 description 2
- 150000002900 organolithium compounds Chemical class 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- 230000021715 photosynthesis, light harvesting Effects 0.000 description 2
- 239000011164 primary particle Substances 0.000 description 2
- ODLMAHJVESYWTB-UHFFFAOYSA-N propylbenzene Chemical compound CCCC1=CC=CC=C1 ODLMAHJVESYWTB-UHFFFAOYSA-N 0.000 description 2
- 150000003335 secondary amines Chemical class 0.000 description 2
- 150000004760 silicates Chemical class 0.000 description 2
- 239000010703 silicon Substances 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000012453 solvate Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 229920003051 synthetic elastomer Polymers 0.000 description 2
- 239000005061 synthetic rubber Substances 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- AHAREKHAZNPPMI-AATRIKPKSA-N (3e)-hexa-1,3-diene Chemical compound CC\C=C\C=C AHAREKHAZNPPMI-AATRIKPKSA-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
- WVAFEFUPWRPQSY-UHFFFAOYSA-N 1,2,3-tris(ethenyl)benzene Chemical compound C=CC1=CC=CC(C=C)=C1C=C WVAFEFUPWRPQSY-UHFFFAOYSA-N 0.000 description 1
- WWOFGTSYQPBRHF-UHFFFAOYSA-N 1,2,4-tris(chloromethyl)benzene Chemical compound ClCC1=CC=C(CCl)C(CCl)=C1 WWOFGTSYQPBRHF-UHFFFAOYSA-N 0.000 description 1
- QLLUAUADIMPKIH-UHFFFAOYSA-N 1,2-bis(ethenyl)naphthalene Chemical compound C1=CC=CC2=C(C=C)C(C=C)=CC=C21 QLLUAUADIMPKIH-UHFFFAOYSA-N 0.000 description 1
- LZDKZFUFMNSQCJ-UHFFFAOYSA-N 1,2-diethoxyethane Chemical compound CCOCCOCC LZDKZFUFMNSQCJ-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- UWFRVQVNYNPBEF-UHFFFAOYSA-N 1-(2,4-dimethylphenyl)propan-1-one Chemical compound CCC(=O)C1=CC=C(C)C=C1C UWFRVQVNYNPBEF-UHFFFAOYSA-N 0.000 description 1
- GDXHBFHOEYVPED-UHFFFAOYSA-N 1-(2-butoxyethoxy)butane Chemical compound CCCCOCCOCCCC GDXHBFHOEYVPED-UHFFFAOYSA-N 0.000 description 1
- UYMQPNRUQXPLCY-UHFFFAOYSA-N 1-(2-piperidin-1-ylethyl)piperidine Chemical compound C1CCCCN1CCN1CCCCC1 UYMQPNRUQXPLCY-UHFFFAOYSA-N 0.000 description 1
- HBIXFRSMLXSLQI-UHFFFAOYSA-N 1-(2-pyrrolidin-1-ylethyl)pyrrolidine Chemical compound C1CCCN1CCN1CCCC1 HBIXFRSMLXSLQI-UHFFFAOYSA-N 0.000 description 1
- KZVBBTZJMSWGTK-UHFFFAOYSA-N 1-[2-(2-butoxyethoxy)ethoxy]butane Chemical compound CCCCOCCOCCOCCCC KZVBBTZJMSWGTK-UHFFFAOYSA-N 0.000 description 1
- AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- NVZWEEGUWXZOKI-UHFFFAOYSA-N 1-ethenyl-2-methylbenzene Chemical compound CC1=CC=CC=C1C=C NVZWEEGUWXZOKI-UHFFFAOYSA-N 0.000 description 1
- JZHGRUMIRATHIU-UHFFFAOYSA-N 1-ethenyl-3-methylbenzene Chemical compound CC1=CC=CC(C=C)=C1 JZHGRUMIRATHIU-UHFFFAOYSA-N 0.000 description 1
- RRQYJINTUHWNHW-UHFFFAOYSA-N 1-ethoxy-2-(2-ethoxyethoxy)ethane Chemical compound CCOCCOCCOCC RRQYJINTUHWNHW-UHFFFAOYSA-N 0.000 description 1
- QEDJMOONZLUIMC-UHFFFAOYSA-N 1-tert-butyl-4-ethenylbenzene Chemical compound CC(C)(C)C1=CC=C(C=C)C=C1 QEDJMOONZLUIMC-UHFFFAOYSA-N 0.000 description 1
- GGPLWEZGITVTJX-UHFFFAOYSA-N 2,2,4-trimethyl-1,4,2-oxazasilinane Chemical compound CN1CCO[Si](C)(C)C1 GGPLWEZGITVTJX-UHFFFAOYSA-N 0.000 description 1
- CWUHERHJSPPFHQ-UHFFFAOYSA-N 2,2-dimethyloxasilinane Chemical compound C[Si]1(C)CCCCO1 CWUHERHJSPPFHQ-UHFFFAOYSA-N 0.000 description 1
- NUNQKTCKURIZQX-UHFFFAOYSA-N 2-(2-ethoxyethoxy)-2-methylpropane Chemical compound CCOCCOC(C)(C)C NUNQKTCKURIZQX-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- VUFKMYLDDDNUJS-UHFFFAOYSA-N 2-(ethoxymethyl)oxolane Chemical compound CCOCC1CCCO1 VUFKMYLDDDNUJS-UHFFFAOYSA-N 0.000 description 1
- YCRFDHHKONBVBR-UHFFFAOYSA-N 2-(hexoxymethyl)oxolane Chemical compound CCCCCCOCC1CCCO1 YCRFDHHKONBVBR-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- KWGJJEBPCVMBIG-UHFFFAOYSA-N 2-methyl-2-[2-[(2-methylpropan-2-yl)oxy]ethoxy]propane Chemical compound CC(C)(C)OCCOC(C)(C)C KWGJJEBPCVMBIG-UHFFFAOYSA-N 0.000 description 1
- RJMRCNBBTPROCR-UHFFFAOYSA-N 2-methyl-2-[2-[2-[(2-methylpropan-2-yl)oxy]ethoxy]ethoxy]propane Chemical compound CC(C)(C)OCCOCCOC(C)(C)C RJMRCNBBTPROCR-UHFFFAOYSA-N 0.000 description 1
- GAODDBNJCKQQDY-UHFFFAOYSA-N 2-methyl-4,6-bis(octylsulfanylmethyl)phenol Chemical compound CCCCCCCCSCC1=CC(C)=C(O)C(CSCCCCCCCC)=C1 GAODDBNJCKQQDY-UHFFFAOYSA-N 0.000 description 1
- QRQKCMFVJWNKQI-UHFFFAOYSA-N 4-(2-morpholin-4-ylethyl)morpholine Chemical compound C1COCCN1CCN1CCOCC1 QRQKCMFVJWNKQI-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
- HVCNXQOWACZAFN-UHFFFAOYSA-N 4-ethylmorpholine Chemical compound CCN1CCOCC1 HVCNXQOWACZAFN-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- ZATOFRITFRPYBT-UHFFFAOYSA-N C1=CC=C2C([Li])=CC=CC2=C1 Chemical compound C1=CC=C2C([Li])=CC=CC2=C1 ZATOFRITFRPYBT-UHFFFAOYSA-N 0.000 description 1
- RIYPCBRPUKZHBO-UHFFFAOYSA-N CC[Si+]1(CC)OCCCC1 Chemical compound CC[Si+]1(CC)OCCCC1 RIYPCBRPUKZHBO-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- VHOQXEIFYTTXJU-UHFFFAOYSA-N Isobutylene-isoprene copolymer Chemical compound CC(C)=C.CC(=C)C=C VHOQXEIFYTTXJU-UHFFFAOYSA-N 0.000 description 1
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 1
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 1
- ZWXPDGCFMMFNRW-UHFFFAOYSA-N N-methylcaprolactam Chemical compound CN1CCCCCC1=O ZWXPDGCFMMFNRW-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical class CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 229910018540 Si C Inorganic materials 0.000 description 1
- 229910018557 Si O Inorganic materials 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 1
- 239000011954 Ziegler–Natta catalyst Substances 0.000 description 1
- FMRLDPWIRHBCCC-UHFFFAOYSA-L Zinc carbonate Chemical compound [Zn+2].[O-]C([O-])=O FMRLDPWIRHBCCC-UHFFFAOYSA-L 0.000 description 1
- XZKRXPZXQLARHH-XVNBXDOJSA-N [(1e)-buta-1,3-dienyl]benzene Chemical compound C=C\C=C\C1=CC=CC=C1 XZKRXPZXQLARHH-XVNBXDOJSA-N 0.000 description 1
- WXZIKFXSSPSWSR-UHFFFAOYSA-N [Li]CCCCC Chemical compound [Li]CCCCC WXZIKFXSSPSWSR-UHFFFAOYSA-N 0.000 description 1
- CPNOVDWZRIYWQV-UHFFFAOYSA-N [Li]CCCCCCCC Chemical compound [Li]CCCCCCCC CPNOVDWZRIYWQV-UHFFFAOYSA-N 0.000 description 1
- SHJXVDAAVHAKFB-UHFFFAOYSA-N [Li]CCCCCCCCCC Chemical compound [Li]CCCCCCCCCC SHJXVDAAVHAKFB-UHFFFAOYSA-N 0.000 description 1
- GERQLUSJPHOXMA-UHFFFAOYSA-N [Li]CCCCCCOC1CCCCO1 Chemical compound [Li]CCCCCCOC1CCCCO1 GERQLUSJPHOXMA-UHFFFAOYSA-N 0.000 description 1
- BZEZSORUWZUMNU-UHFFFAOYSA-N [Li]CCCC[Li] Chemical compound [Li]CCCC[Li] BZEZSORUWZUMNU-UHFFFAOYSA-N 0.000 description 1
- SDENQAIPKIPKCA-UHFFFAOYSA-N [Li]CCCO[Si](C)(C)C(C)(C)C Chemical compound [Li]CCCO[Si](C)(C)C(C)(C)C SDENQAIPKIPKCA-UHFFFAOYSA-N 0.000 description 1
- 238000005299 abrasion Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 150000001266 acyl halides Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 229910052915 alkaline earth metal silicate Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- NTXGQCSETZTARF-UHFFFAOYSA-N buta-1,3-diene;prop-2-enenitrile Chemical compound C=CC=C.C=CC#N NTXGQCSETZTARF-UHFFFAOYSA-N 0.000 description 1
- 235000013844 butane Nutrition 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 1
- 239000000292 calcium oxide Substances 0.000 description 1
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 1
- 239000000378 calcium silicate Substances 0.000 description 1
- 229910052918 calcium silicate Inorganic materials 0.000 description 1
- OYACROKNLOSFPA-UHFFFAOYSA-N calcium;dioxido(oxo)silane Chemical compound [Ca+2].[O-][Si]([O-])=O OYACROKNLOSFPA-UHFFFAOYSA-N 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- LEKSIJZGSFETSJ-UHFFFAOYSA-N cyclohexane;lithium Chemical compound [Li]C1CCCCC1 LEKSIJZGSFETSJ-UHFFFAOYSA-N 0.000 description 1
- RJGHQTVXGKYATR-UHFFFAOYSA-L dibutyl(dichloro)stannane Chemical compound CCCC[Sn](Cl)(Cl)CCCC RJGHQTVXGKYATR-UHFFFAOYSA-L 0.000 description 1
- 229940019778 diethylene glycol diethyl ether Drugs 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- SMBQBQBNOXIFSF-UHFFFAOYSA-N dilithium Chemical compound [Li][Li] SMBQBQBNOXIFSF-UHFFFAOYSA-N 0.000 description 1
- LIKFHECYJZWXFJ-UHFFFAOYSA-N dimethyldichlorosilane Chemical compound C[Si](C)(Cl)Cl LIKFHECYJZWXFJ-UHFFFAOYSA-N 0.000 description 1
- POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 1
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000000806 elastomer Substances 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- 238000007720 emulsion polymerization reaction Methods 0.000 description 1
- BLHLJVCOVBYQQS-UHFFFAOYSA-N ethyllithium Chemical compound [Li]CC BLHLJVCOVBYQQS-UHFFFAOYSA-N 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 239000004088 foaming agent Substances 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 239000012760 heat stabilizer Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 1
- 231100000086 high toxicity Toxicity 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 229920006168 hydrated nitrile rubber Polymers 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000003993 interaction 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
- 239000004611 light stabiliser Substances 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- CETVQRFGPOGIQJ-UHFFFAOYSA-N lithium;hexane Chemical compound [Li+].CCCCC[CH2-] CETVQRFGPOGIQJ-UHFFFAOYSA-N 0.000 description 1
- DWNRISLZVCBTRN-UHFFFAOYSA-N lithium;piperidin-1-ide Chemical compound [Li]N1CCCCC1 DWNRISLZVCBTRN-UHFFFAOYSA-N 0.000 description 1
- SZAVVKVUMPLRRS-UHFFFAOYSA-N lithium;propane Chemical compound [Li+].C[CH-]C SZAVVKVUMPLRRS-UHFFFAOYSA-N 0.000 description 1
- FJDQVJUXXNIHNB-UHFFFAOYSA-N lithium;pyrrolidin-1-ide Chemical compound [Li+].C1CC[N-]C1 FJDQVJUXXNIHNB-UHFFFAOYSA-N 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- HCWCAKKEBCNQJP-UHFFFAOYSA-N magnesium orthosilicate Chemical compound [Mg+2].[Mg+2].[O-][Si]([O-])([O-])[O-] HCWCAKKEBCNQJP-UHFFFAOYSA-N 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- 239000000391 magnesium silicate Substances 0.000 description 1
- 229910052919 magnesium silicate Inorganic materials 0.000 description 1
- 235000019792 magnesium silicate Nutrition 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 229910000000 metal hydroxide Inorganic materials 0.000 description 1
- 150000004692 metal hydroxides Chemical class 0.000 description 1
- 239000005055 methyl trichlorosilane Substances 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 description 1
- JLUFWMXJHAVVNN-UHFFFAOYSA-N methyltrichlorosilane Chemical compound C[Si](Cl)(Cl)Cl JLUFWMXJHAVVNN-UHFFFAOYSA-N 0.000 description 1
- 239000011325 microbead Substances 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical class CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 description 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Natural products CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920001084 poly(chloroprene) Polymers 0.000 description 1
- 239000011591 potassium Substances 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
- 238000011084 recovery Methods 0.000 description 1
- 238000010058 rubber compounding Methods 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 229910010271 silicon carbide Inorganic materials 0.000 description 1
- LIVNPJMFVYWSIS-UHFFFAOYSA-N silicon monoxide Inorganic materials [Si-]#[O+] LIVNPJMFVYWSIS-UHFFFAOYSA-N 0.000 description 1
- 239000005049 silicon tetrachloride Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000011667 zinc carbonate Substances 0.000 description 1
- 229910000010 zinc carbonate Inorganic materials 0.000 description 1
- 235000004416 zinc carbonate Nutrition 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 229910052726 zirconium Inorganic materials 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
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B60—VEHICLES IN GENERAL
- B60C—VEHICLE TYRES; TYRE INFLATION; TYRE CHANGING; CONNECTING VALVES TO INFLATABLE ELASTIC BODIES IN GENERAL; DEVICES OR ARRANGEMENTS RELATED TO TYRES
- B60C1/00—Tyres characterised by the chemical composition or the physical arrangement or mixture of the composition
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08C—TREATMENT OR CHEMICAL MODIFICATION OF RUBBERS
- C08C19/00—Chemical modification of rubber
- C08C19/25—Incorporating silicon atoms into the molecule
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08C—TREATMENT OR CHEMICAL MODIFICATION OF RUBBERS
- C08C19/00—Chemical modification of rubber
- C08C19/30—Addition of a reagent which reacts with a hetero atom or a group containing hetero atoms of the macromolecule
- C08C19/42—Addition of a reagent which reacts with a hetero atom or a group containing hetero atoms of the macromolecule reacting with metals or metal-containing groups
- C08C19/44—Addition of a reagent which reacts with a hetero atom or a group containing hetero atoms of the macromolecule reacting with metals or metal-containing groups of polymers containing metal atoms exclusively at one or both ends of the skeleton
-
- 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
- C08F2/00—Processes of polymerisation
- C08F2/38—Polymerisation using regulators, e.g. chain terminating agents, e.g. telomerisation
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L15/00—Compositions of rubber derivatives
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/34—Silicon-containing compounds
- C08K3/36—Silica
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/54—Silicon-containing compounds
- C08K5/541—Silicon-containing compounds containing oxygen
- C08K5/5415—Silicon-containing compounds containing oxygen containing at least one Si—O bond
- C08K5/5419—Silicon-containing compounds containing oxygen containing at least one Si—O bond containing at least one Si—C bond
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/54—Silicon-containing compounds
- C08K5/548—Silicon-containing compounds containing sulfur
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L9/00—Compositions of homopolymers or copolymers of conjugated diene hydrocarbons
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Mechanical Engineering (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Silicon Polymers (AREA)
- Polyesters Or Polycarbonates (AREA)
Abstract
Description
R1、R2、R3、R4は、同一であるかまたは異なっており、H、アルキル基、シクロアルキル基、アリール基、アルカリル基、およびアラルキル基であるが、ここでそれらには、ヘテロ原子たとえばO、N、S、Siが含まれていてもよく、
Aは、CおよびHに加えて、ヘテロ原子たとえばO、N、S、Siを含んでいてよい、二価の有機基である。]
R1、R2、R3、R4は、同一であるかまたは異なっており、H、アルキル基、シクロアルキル基、アリール基、アルカリル基、およびアラルキル基であるが、ここでそれらには、ヘテロ原子たとえばO、N、S、Siが含まれていてもよく、
Aは、CおよびHに加えて、ヘテロ原子たとえばO、N、S、Siを含んでいてよい、二価の有機基であり、
nは、1〜4の整数であり、
Mは、原子価1〜4の金属または半金属、好ましくは、Li、Na、K、Mg、Ca、Fe、Co、Ni、Al、Nd、Ti、Si、Snである。]
R1、R2、R3、R4は、同一であるかまたは異なっており、H、アルキル基、シクロアルキル基、アリール基、アルカリル基、およびアラルキル基であるが、ここでそれらには、ヘテロ原子たとえばO、N、S、Siが含まれていてもよく、
Aは、CおよびHに加えて、ヘテロ原子たとえばO、N、S、Siを含んでいてよい、二価の有機基である。]
2,2−ジメチル−1−オキサ−2−シラシクロヘキサン
BR:ポリブタジエン
ABR:ブタジエン/アクリル酸C1〜C4−アルキル・コポリマー
IR:ポリイソプレン
ESBR:スチレン−ブタジエンコポリマー(乳化重合で製造され、スチレン含量が1〜60重量%、好ましくは20〜50重量%のもの)
SSBR:スチレン−ブタジエンコポリマー(溶液重合で製造され、スチレン含量が1〜60重量%、好ましくは15〜45重量%のもの)
IIR:イソブチレン−イソプレンコポリマー
NBR:ブタジエン−アクリロニトリルコポリマー(アクリロニトリル含量が、5〜60重量%、好ましくは10〜40重量%のもの)
HNBR:部分水素化または完全水素化NBRゴム
EPDM:エチレン−プロピレン−ジエンターポリマー
ならびに前記ゴムの混合物。自動車用タイヤを製造するために興味のある材料は、特に、天然ゴム、ガラス転移温度が−60℃よりも高いESBRおよびSSBR、高cis含量(>90%)を有するポリブタジエンゴム(Ni、Co、Ti、またはNdをベースとする触媒を使用して製造されたもの)、さらには80%までのビニル含量を有するポリブタジエンゴム、ならびにそれらの混合物である。
・ 微粒子シリカ、たとえばシリケートの溶液からの沈降法またはハロゲン化ケイ素の火炎加水分解法で製造され、比表面積(BET表面積)が5〜1000m2/g、好ましくは20〜400m2/gであり、一次粒径が10〜400nmであるもの。それらのシリカは、適切であるならば、他の金属の酸化物たとえばAl酸化物、Mg酸化物、Ca酸化物、Ba酸化物、Zn酸化物、Zr酸化物、またはTi酸化物との混合酸化物の形態をとることもできる;
・ 合成シリケート、たとえばケイ酸アルミニウム、またはアルカリ土類金属シリケート、たとえば、ケイ酸マグネシウムもしくはケイ酸カルシウムで、BET表面積が20〜400m2/gで、一次粒径が10〜400nmのもの;
・ 天然シリケート、たとえばカオリン、およびその他各種の天然のシリカの形態のもの;
・ ガラス繊維およびガラス繊維製品(マット、ストランド)、またはガラスマイクロビーズ;
・ 金属酸化物たとえば、酸化亜鉛、酸化カルシウム、酸化マグネシウム、または酸化アルミニウム;
・ 金属炭酸塩たとえば、炭酸マグネシウム、炭酸カルシウム、または炭酸亜鉛;
・ 金属水酸化物たとえば、水酸化アルミニウムまたは水酸化マグネシウム;
・ 金属硫酸塩たとえば、硫酸カルシウムまたは硫酸バリウム;
・ カーボンブラック:ここで使用されるカーボンブラックは、火炎法、チャンネル法、ファーネス法、ガス法、加熱法、アセチレン法、またはアーク法によって調製されたものであって、それらのBET表面積が9〜200m2/gであり、例を挙げれば、SAF、ISAF−LS、ISAF−HM、ISAF−LM、ISAF−HS、CF、SCF、HAF−LS、HAF、HAF−HS、FF−HS、SPF、XCF、FEF−LS、FEF、FEF−HS、GPF−HS、GPF、APF、SRF−LS、SRF−LM、SRF−HS、SRF−HM、およびMTカーボンブラック、またはASTMに従って下記のように分類されるカーボンブラック:N110、N219、N220、N231、N234、N242、N294、N326、N327、N330、N332、N339、N347、N351、N356、N358、N375、N472、N539、N550、N568、N650、N660、N754、N762、N765、N774、N787、およびN990カーボンブラックである;
・ ゴムゲル、特にBR、ESBRおよび/またはポリクロロプレンをベースとした、5〜1000nmの粒径を有するもの。
以下のものを、不活性環境とした20Lの反応器に仕込んだ:8.5kgのヘキサン、1125gの1,3−ブタジエン、375gのスチレン、28mmolの2,2−ビス(2−テトラヒドロフリル)プロパン、さらには10mmolのブチルリチウム。その内容物を加熱して70℃とした。その混合物を、撹拌しながら70℃で1時間かけて重合させた。次いでそのゴム溶液を取り出し、3gのIrganox(登録商標)1520(2,4−ビス(オクチルチオメチル)−6−メチルフェノール)を添加することによって安定化させ、水蒸気ストリッピングによって溶媒を除去した。真空中65℃で、そのゴム片を乾燥させた。
以下のものを、不活性環境とした20Lの反応器に仕込んだ:8.5kgのヘキサン、1125gの1,3−ブタジエン、375gのスチレン、28mmolの2,2−ビス(2−テトラヒドロフリル)プロパン、さらには10mmolのブチルリチウム。その内容物を加熱して70℃とした。その混合物を、撹拌しながら70℃で1時間かけて重合させた。次いで、11mmol(1.43g)の2,2−ジメチル−1−オキサ−2−シラシクロヘキサンを添加し、反応器の内容物をさらに20分間70℃に加熱した。次いでそのゴム溶液を取り出し、3gのIrganox(登録商標)1520を添加することによって安定化させ、水蒸気ストリッピングによって溶媒を除去した。真空中65℃で、そのゴム片を乾燥させた。
以下のものを、不活性環境とした20Lの反応器に仕込んだ:8.5kgのヘキサン、1125gの1,3−ブタジエン、375gのスチレン、28mmolの2,2−ビス(2−テトラヒドロフリル)プロパン、さらには10.5mmolのブチルリチウム。その内容物を加熱して70℃とした。その混合物を、撹拌しながら70℃で1時間かけて重合させた。次いで、11.6mmol(1.69g)の2,2,4−トリメチル−1−オキサ−4−アザ−2−シラシクロヘキサンを添加し、その反応器の内容物をさらに20分間70℃に加熱した。次いでそのゴム溶液を取り出し、3gのIrganox(登録商標)1520を添加することによって安定化させ、水蒸気ストリッピングによって溶媒を除去した。真空中65℃で、そのゴム片を乾燥させた。
タイヤトレッドゴム組成物を製造したが、それには、比較例としての例1からのスチレン−ブタジエンコポリマー(ゴム組成物2a)、さらには、実施例1bおよび1cからの本発明のシラン含有カルビノール末端化スチレン−ブタジエンコポリマー(ゴム組成物2bおよび2c)が含まれる。表1にそれらの構成成分を列記した。ゴム組成物(硫黄および加硫促進剤なし)は、1.5Lのニーダー中で製造した。次いで、構成成分の硫黄および加硫促進剤を、40℃でロール上で混ぜ込んだ。
表1に記載の例2a〜cのタイヤトレッドゴム組成物を、160℃で20分かけて加硫させた。それらに相当する加硫物の物性を、表2の例3a〜cとして列記した。
Claims (23)
- 前記ポリマーの前記末端基が、式(II)の金属塩の形態で存在していることを特徴とする、請求項1に記載の、末端基によって官能化されたポリマー
R1、R2、R3、R4は、同一であるかまたは異なっており、H、アルキル基、シクロアルキル基、アリール基、アルカリル基、およびアラルキル基であるが、ここでそれらには、ヘテロ原子たとえばO、N、S、Siが含まれていてもよく、
Aは、CおよびHに加えて、ヘテロ原子たとえばO、N、S、Siを含んでいてよい、二価の有機基であり、
nは、1〜4の整数であり、
Mは、原子価1〜4の金属または半金属、好ましくは、Li、Na、K、Mg、Ca、Fe、Co、Ni、Al、Nd、Ti、Si、Snである]。 - 前記ポリマーが、ジエンポリマーであるか、またはジエンをビニル芳香族モノマーと共重合させることを介して得ることが可能なジエンコポリマーであることを特徴とする、請求項1または2に記載の、末端基によって官能化されたポリマー。
- 前記ジエンポリマーが、ポリブタジエン、ポリイソプレン、ブタジエン−イソプレンコポリマー、ブタジエン−スチレンコポリマー、イソプレン−スチレンコポリマー、またはブタジエン−イソプレン−スチレンターポリマーであることを特徴とする、請求項3に記載の、末端基によって官能化されたポリマー。
- 官能化反応剤として、1種または複数の1−オキサ−2−シラシクロアルカンが使用されることを特徴とする、請求項4に記載の、末端基によって官能化されたポリマー。
- 前記ポリマーの平均モル質量(数平均)が、10 000〜2 000 000g/mol、好ましくは100 000〜1 000 000g/molであることを特徴とする、請求項6に記載の、末端基によって官能化されたポリマー。
- 前記ポリマーのガラス転移温度が、−110℃〜+20℃、好ましくは110℃〜0℃であることを特徴とする、請求項7に記載の、末端基によって官能化されたポリマー。
- 前記ポリマーのムーニー粘度[ML 1+4(100℃)]が、10〜200、好ましくは30〜150ムーニー単位であることを特徴とする、請求項8に記載の、末端基によって官能化されたポリマー。
- 請求項1または2に記載の、末端基によって官能化されたポリマーを製造するための官能化反応剤としての、1−オキサ−2−シラシクロアルカンの使用。
- 反応性のポリマー鎖末端を有するポリマーに対して、1種または複数の1−オキサ−2−シラシクロアルカン(官能化反応剤)を添加することを特徴とする、末端基によって官能化されたポリマーを製造するための方法。
- 重合プロセスの完了後に、前記官能化反応剤の添加を実施することを特徴とする、請求項11に記載の方法。
- 過剰の官能化反応剤を使用することを特徴とする、請求項11に記載の方法。
- 化学量論量または準化学量論量の官能化反応剤を使用することを特徴とする、請求項11に記載の方法。
- 官能化反応剤の量が、反応性のポリマー鎖末端を有するポリマーの量を基準にして、0.005〜2重量%、好ましくは0.01〜1重量%であることを特徴とする、請求項13または14のいずれかに記載の方法。
- 前記反応性のポリマー鎖末端との反応のために、カップリング剤を使用することを特徴とする、請求項11〜15のいずれか一項に記載の方法。
- 加硫可能なゴム組成物を製造するための、請求項1〜9のいずれか一項に記載の、末端基によって官能化されたポリマーの使用。
- 抗酸化剤、オイル、充填剤、ゴム、および/またはゴム助剤を含むことを特徴とする、請求項17に記載の加硫可能なゴム組成物。
- 式(I)または(II)の末端基を有する、末端基によって官能化されたポリマーを含む、加硫可能なゴム組成物。
- タイヤ、特にタイヤトレッドを製造するための、請求項19に記載の加硫可能なゴム組成物の使用。
- 成形物、特にケーブル外装、ホース、伝動ベルト、コンベア用ベルト、ロール被覆、靴底、シーリング、および制振要素を製造するための、請求項19に記載の加硫可能なゴム組成物の使用。
- 請求項20に従って得ることが可能な、タイヤ。
- 請求項21に従って得ることが可能な、成形物。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP10191342.4 | 2010-11-16 | ||
EP10191342A EP2452951A1 (de) | 2010-11-16 | 2010-11-16 | Silanhaltige carbinolterminierte Polymere |
PCT/EP2011/069913 WO2012065908A1 (de) | 2010-11-16 | 2011-11-11 | Silanhaltige carbinolterminierte polymere |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2013544303A true JP2013544303A (ja) | 2013-12-12 |
JP5845278B2 JP5845278B2 (ja) | 2016-01-20 |
Family
ID=43608120
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2013539207A Active JP5845278B2 (ja) | 2010-11-16 | 2011-11-11 | シラン含有カルビノール末端化ポリマー |
Country Status (15)
Country | Link |
---|---|
US (1) | US9587059B2 (ja) |
EP (3) | EP2452951A1 (ja) |
JP (1) | JP5845278B2 (ja) |
KR (2) | KR101716539B1 (ja) |
CN (1) | CN103221433B (ja) |
BR (1) | BR112013012201B1 (ja) |
ES (1) | ES2780204T3 (ja) |
HU (1) | HUE048869T2 (ja) |
MX (1) | MX352977B (ja) |
MY (1) | MY181369A (ja) |
PL (1) | PL3056520T3 (ja) |
RU (1) | RU2591254C2 (ja) |
SA (1) | SA111320917B1 (ja) |
TW (1) | TWI518097B (ja) |
WO (1) | WO2012065908A1 (ja) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2016194018A (ja) * | 2015-04-01 | 2016-11-17 | 東洋ゴム工業株式会社 | ゴム組成物の製造方法 |
JP2022509159A (ja) * | 2018-11-23 | 2022-01-20 | パブリック・ジョイント・ストック・カンパニー・“シブール・ホールディング” | ポリマー組成物及びその調製方法 |
Families Citing this family (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP2662392A1 (de) * | 2012-05-09 | 2013-11-13 | LANXESS Deutschland GmbH | Allylaminhaltige, carbinolterminierte Polymere |
EP2662406A1 (de) * | 2012-05-09 | 2013-11-13 | LANXESS Deutschland GmbH | Aminhaltige, carbinolterminierte Polymere |
EP2796485A1 (de) | 2013-04-24 | 2014-10-29 | LANXESS Deutschland GmbH | Cold Flow reduzierte Polymere mit gutem Verarbeitungsverhalten |
EP2796471A1 (de) * | 2013-04-24 | 2014-10-29 | LANXESS Deutschland GmbH | Silanhaltige carboxyterminierte Polymere |
EP2865540A1 (de) | 2013-10-24 | 2015-04-29 | LANXESS Deutschland GmbH | Kautschukzusammensetzung |
ES2775499T3 (es) * | 2015-05-13 | 2020-07-27 | Evonik Operations Gmbh | Mejora de la resistencia a la rodadura de neumáticos de caucho diénico mediante polibutadienos modificados con silano |
EP3366709A1 (en) * | 2017-02-24 | 2018-08-29 | ARLANXEO Deutschland GmbH | In-chain phosphine- and phosphonium- containing diene-polymers |
JP6959751B2 (ja) | 2017-03-31 | 2021-11-05 | 株式会社クレハ | フッ化ビニリデン共重合体粒子及びその利用 |
RU2680501C1 (ru) * | 2017-12-12 | 2019-02-21 | Публичное акционерное общество "СИБУР Холдинг" | Способ получения функционализированных сополимеров на основе сопряженных диенов, сополимеры, полученные этим способом, резиновые смеси на основе данных сополимеров |
RU2675525C1 (ru) * | 2017-12-12 | 2018-12-19 | Публичное акционерное общество "СИБУР Холдинг" | Сополимеры сопряженных диенов и винилароматических мономеров и способ их получения. Резиновые смеси на основе указанных сополимеров |
US11208518B2 (en) | 2018-12-11 | 2021-12-28 | The Goodyear Tire & Rubber Company | Functionalized polymer, rubber composition and pneumatic tire |
WO2023021004A1 (en) | 2021-08-17 | 2023-02-23 | Arlanxeo Deutschland Gmbh | Functionalized polymers |
WO2023104784A1 (en) | 2021-12-07 | 2023-06-15 | Arlanxeo Deutschland Gmbh | Diene rubbers prepared with unsaturated siloxane-based coupling agents |
WO2023152146A1 (en) | 2022-02-11 | 2023-08-17 | Arlanxeo Deutschland Gmbh | Modified diene rubbers |
WO2023247719A1 (en) | 2022-06-23 | 2023-12-28 | Arlanxeo Deutschland Gmbh | Alpha-omega-functionalized polymers |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH0718077A (ja) * | 1993-06-14 | 1995-01-20 | Dow Corning Corp | カルビノール・官能シロキサンの製造法 |
JPH0859739A (ja) * | 1994-08-25 | 1996-03-05 | Bridgestone Corp | アルコキシシラン変性重合体及びそれを用いた接着剤組成物 |
WO2003048216A1 (fr) * | 2001-12-03 | 2003-06-12 | Bridgestone Corporation | Procede de production de polymere modifie, polymere modifie obtenu par ce procede et composition de caoutchouc |
JP2003171418A (ja) * | 2001-09-27 | 2003-06-20 | Jsr Corp | 共役ジオレフィン(共)重合ゴム、該(共)重合ゴムの製造方法、ゴム組成物およびタイヤ |
JP2009513761A (ja) * | 2005-10-27 | 2009-04-02 | ウァッカー ケミー アーゲー | ポリエステルポリシロキサン共重合体およびその製造方法 |
Family Cites Families (18)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3244664A (en) | 1960-10-24 | 1966-04-05 | Phillips Petroleum Co | Silicon-containing polymers |
GB1597500A (en) | 1977-12-29 | 1981-09-09 | Shell Int Research | Polymers |
US4417029A (en) | 1981-08-03 | 1983-11-22 | Atlantic Richfield Company | Derivatization of star-block copolymers |
SU1165682A1 (ru) * | 1984-03-21 | 1985-07-07 | Уфимский Нефтяной Институт | Способ получени 2,2-диэтил-1,3-диокса-2-силациклогексанов |
US4616069A (en) | 1984-10-26 | 1986-10-07 | Nippon Zeon Co., Ltd. | Process for making diene polymer rubbers |
US4618650A (en) | 1985-09-04 | 1986-10-21 | The Goodyear Tire & Rubber Company | Siloxane containing network polymer |
FR2740778A1 (fr) | 1995-11-07 | 1997-05-09 | Michelin & Cie | Composition de caoutchouc a base de silice et de polymere dienique fonctionalise ayant une fonction silanol terminale |
JP3622803B2 (ja) | 1995-11-28 | 2005-02-23 | 日本ゼオン株式会社 | ゴム組成物 |
US5659056A (en) | 1996-04-10 | 1997-08-19 | Bridgestone Corporation | Stabilization of siloxane terminated polymers |
US6008295A (en) | 1997-07-11 | 1999-12-28 | Bridgestone Corporation | Diene polymers and copolymers incorporating partial coupling and terminals formed from hydrocarboxysilane compounds |
US6384117B1 (en) | 1997-07-11 | 2002-05-07 | Bridgestone Corporation | Processability of silica-filled rubber stocks |
US6255404B1 (en) | 1999-07-26 | 2001-07-03 | Bridgestone Corporation | Method to control increase in viscosity during aging of siloxane modified polymers |
US6279632B1 (en) | 1999-11-24 | 2001-08-28 | Bridgestone Corporation | Method to control increase in viscosity during aging of siloxane modified polymers |
TWI385182B (zh) | 2004-03-15 | 2013-02-11 | Jsr Corp | Conjugated diene (co) poly rubber and method for producing the same |
JP4963786B2 (ja) | 2004-11-26 | 2012-06-27 | 株式会社ブリヂストン | 変性天然ゴムラテックス及びその製造方法、変性天然ゴム及びその製造方法、並びにゴム組成物及びタイヤ |
WO2006076629A1 (en) * | 2005-01-14 | 2006-07-20 | Bridgestone Corporation | Functionalized polymers and improved tires therefrom |
US7868081B2 (en) * | 2005-03-04 | 2011-01-11 | Bridgestone Corporation | Rubber composition and tire using same |
DE102008052057A1 (de) | 2008-10-16 | 2010-04-22 | Lanxess Deutschland Gmbh | Funktionalisierte Dienkautschuke |
-
2010
- 2010-11-16 EP EP10191342A patent/EP2452951A1/de not_active Withdrawn
-
2011
- 2011-11-11 EP EP16156292.1A patent/EP3056520B1/de active Active
- 2011-11-11 MX MX2013005449A patent/MX352977B/es active IP Right Grant
- 2011-11-11 BR BR112013012201A patent/BR112013012201B1/pt not_active IP Right Cessation
- 2011-11-11 HU HUE16156292A patent/HUE048869T2/hu unknown
- 2011-11-11 KR KR1020137015332A patent/KR101716539B1/ko active IP Right Grant
- 2011-11-11 KR KR1020157018780A patent/KR20150088901A/ko not_active Application Discontinuation
- 2011-11-11 MY MYPI2013700785A patent/MY181369A/en unknown
- 2011-11-11 CN CN201180055296.1A patent/CN103221433B/zh active Active
- 2011-11-11 US US13/885,073 patent/US9587059B2/en active Active
- 2011-11-11 ES ES16156292T patent/ES2780204T3/es active Active
- 2011-11-11 EP EP11784467.0A patent/EP2640753A1/de not_active Withdrawn
- 2011-11-11 PL PL16156292T patent/PL3056520T3/pl unknown
- 2011-11-11 WO PCT/EP2011/069913 patent/WO2012065908A1/de active Application Filing
- 2011-11-11 RU RU2013127128/05A patent/RU2591254C2/ru active
- 2011-11-11 JP JP2013539207A patent/JP5845278B2/ja active Active
- 2011-11-15 TW TW100141517A patent/TWI518097B/zh not_active IP Right Cessation
- 2011-11-16 SA SA111320917A patent/SA111320917B1/ar unknown
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH0718077A (ja) * | 1993-06-14 | 1995-01-20 | Dow Corning Corp | カルビノール・官能シロキサンの製造法 |
JPH0859739A (ja) * | 1994-08-25 | 1996-03-05 | Bridgestone Corp | アルコキシシラン変性重合体及びそれを用いた接着剤組成物 |
JP2003171418A (ja) * | 2001-09-27 | 2003-06-20 | Jsr Corp | 共役ジオレフィン(共)重合ゴム、該(共)重合ゴムの製造方法、ゴム組成物およびタイヤ |
WO2003048216A1 (fr) * | 2001-12-03 | 2003-06-12 | Bridgestone Corporation | Procede de production de polymere modifie, polymere modifie obtenu par ce procede et composition de caoutchouc |
JP2009513761A (ja) * | 2005-10-27 | 2009-04-02 | ウァッカー ケミー アーゲー | ポリエステルポリシロキサン共重合体およびその製造方法 |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2016194018A (ja) * | 2015-04-01 | 2016-11-17 | 東洋ゴム工業株式会社 | ゴム組成物の製造方法 |
JP2022509159A (ja) * | 2018-11-23 | 2022-01-20 | パブリック・ジョイント・ストック・カンパニー・“シブール・ホールディング” | ポリマー組成物及びその調製方法 |
JP7212162B2 (ja) | 2018-11-23 | 2023-01-24 | パブリック・ジョイント・ストック・カンパニー・“シブール・ホールディング” | ポリマー組成物及びその調製方法 |
Also Published As
Publication number | Publication date |
---|---|
KR20150088901A (ko) | 2015-08-03 |
EP2452951A1 (de) | 2012-05-16 |
CN103221433A (zh) | 2013-07-24 |
BR112013012201B1 (pt) | 2020-01-21 |
MX352977B (es) | 2017-12-15 |
EP3056520B1 (de) | 2020-02-19 |
KR101716539B1 (ko) | 2017-03-14 |
TWI518097B (zh) | 2016-01-21 |
SA111320917B1 (ar) | 2015-01-22 |
EP3056520A1 (de) | 2016-08-17 |
US20130281605A1 (en) | 2013-10-24 |
ES2780204T3 (es) | 2020-08-24 |
WO2012065908A1 (de) | 2012-05-24 |
TW201241009A (en) | 2012-10-16 |
BR112013012201A2 (pt) | 2019-07-02 |
RU2013127128A (ru) | 2014-12-27 |
MY181369A (en) | 2020-12-21 |
JP5845278B2 (ja) | 2016-01-20 |
HUE048869T2 (hu) | 2020-08-28 |
EP2640753A1 (de) | 2013-09-25 |
CN103221433B (zh) | 2015-04-29 |
RU2591254C2 (ru) | 2016-07-20 |
US9587059B2 (en) | 2017-03-07 |
PL3056520T3 (pl) | 2020-07-13 |
KR20130109186A (ko) | 2013-10-07 |
MX2013005449A (es) | 2013-07-05 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP5845278B2 (ja) | シラン含有カルビノール末端化ポリマー | |
JP6306688B2 (ja) | シラン含有カルボキシル末端化ポリマー | |
JP6215310B2 (ja) | アミン含有カルビノール末端ポリマー | |
US10421825B2 (en) | Methanol-terminated polymers containing ether | |
JP6321630B2 (ja) | アリルアミン含有カルビノール末端ポリマー | |
JP2016518493A (ja) | 良好な加工特性を有する、コールドフローが抑制されたポリマー | |
JP5769812B2 (ja) | トリアルキルシリルオキシ末端化ポリマー |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20140808 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20140818 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20141118 |
|
A02 | Decision of refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A02 Effective date: 20150525 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20150918 |
|
A911 | Transfer to examiner for re-examination before appeal (zenchi) |
Free format text: JAPANESE INTERMEDIATE CODE: A911 Effective date: 20150930 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20151026 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20151120 |
|
R150 | Certificate of patent or registration of utility model |
Ref document number: 5845278 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
S111 | Request for change of ownership or part of ownership |
Free format text: JAPANESE INTERMEDIATE CODE: R313113 |
|
R350 | Written notification of registration of transfer |
Free format text: JAPANESE INTERMEDIATE CODE: R350 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |