JP2022531495A - 変性高シスポリブタジエンポリマー、関連方法及びゴム組成物 - Google Patents
変性高シスポリブタジエンポリマー、関連方法及びゴム組成物 Download PDFInfo
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- JP2022531495A JP2022531495A JP2021566136A JP2021566136A JP2022531495A JP 2022531495 A JP2022531495 A JP 2022531495A JP 2021566136 A JP2021566136 A JP 2021566136A JP 2021566136 A JP2021566136 A JP 2021566136A JP 2022531495 A JP2022531495 A JP 2022531495A
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- 229920000642 polymer Polymers 0.000 title claims abstract description 172
- 238000000034 method Methods 0.000 title claims abstract description 158
- 239000005063 High cis polybutadiene Substances 0.000 title claims abstract description 73
- 239000000203 mixture Substances 0.000 title claims description 136
- 229920001971 elastomer Polymers 0.000 title claims description 99
- 239000005060 rubber Substances 0.000 title claims description 91
- 150000001875 compounds Chemical class 0.000 claims abstract description 164
- 230000008569 process Effects 0.000 claims abstract description 132
- 239000003054 catalyst Substances 0.000 claims abstract description 76
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims abstract description 20
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 189
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 151
- -1 glycidoxy group Chemical group 0.000 claims description 113
- 229910052759 nickel Inorganic materials 0.000 claims description 103
- 239000000945 filler Substances 0.000 claims description 60
- 239000000377 silicon dioxide Substances 0.000 claims description 59
- 229910052747 lanthanoid Inorganic materials 0.000 claims description 43
- 150000002602 lanthanoids Chemical class 0.000 claims description 38
- 125000003118 aryl group Chemical group 0.000 claims description 37
- 230000003197 catalytic effect Effects 0.000 claims description 36
- 150000002601 lanthanoid compounds Chemical class 0.000 claims description 36
- 239000002168 alkylating agent Substances 0.000 claims description 34
- 229940100198 alkylating agent Drugs 0.000 claims description 34
- 229910052782 aluminium Inorganic materials 0.000 claims description 34
- 229910052736 halogen Inorganic materials 0.000 claims description 33
- 238000004073 vulcanization Methods 0.000 claims description 33
- 229920002857 polybutadiene Polymers 0.000 claims description 32
- 150000002367 halogens Chemical class 0.000 claims description 31
- 239000005062 Polybutadiene Substances 0.000 claims description 30
- 125000000217 alkyl group Chemical group 0.000 claims description 30
- 239000003795 chemical substances by application Substances 0.000 claims description 29
- 239000003381 stabilizer Substances 0.000 claims description 29
- 230000003014 reinforcing effect Effects 0.000 claims description 25
- 125000003545 alkoxy group Chemical group 0.000 claims description 24
- 229910052799 carbon Inorganic materials 0.000 claims description 23
- 125000004432 carbon atom Chemical group C* 0.000 claims description 23
- 238000004519 manufacturing process Methods 0.000 claims description 22
- 239000011737 fluorine Substances 0.000 claims description 21
- 229910052731 fluorine Inorganic materials 0.000 claims description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 20
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 20
- 239000010941 cobalt Substances 0.000 claims description 18
- 229910017052 cobalt Inorganic materials 0.000 claims description 18
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 18
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 16
- 239000004593 Epoxy Substances 0.000 claims description 15
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 15
- 244000043261 Hevea brasiliensis Species 0.000 claims description 14
- GJVFBWCTGUSGDD-UHFFFAOYSA-L pentamethonium bromide Chemical compound [Br-].[Br-].C[N+](C)(C)CCCCC[N+](C)(C)C GJVFBWCTGUSGDD-UHFFFAOYSA-L 0.000 claims description 14
- 239000012763 reinforcing filler Substances 0.000 claims description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
- 125000003700 epoxy group Chemical group 0.000 claims description 13
- 150000001721 carbon Chemical group 0.000 claims description 11
- 229920001194 natural rubber Polymers 0.000 claims description 11
- 150000002816 nickel compounds Chemical class 0.000 claims description 11
- 239000012936 vulcanization activator Substances 0.000 claims description 11
- 239000013032 Hydrocarbon resin Substances 0.000 claims description 10
- 229920006270 hydrocarbon resin Polymers 0.000 claims description 10
- 239000003112 inhibitor Substances 0.000 claims description 10
- 229920003052 natural elastomer Polymers 0.000 claims description 10
- 229920001195 polyisoprene Polymers 0.000 claims description 10
- 229910052751 metal Inorganic materials 0.000 claims description 9
- 239000002184 metal Substances 0.000 claims description 9
- 238000010791 quenching Methods 0.000 claims description 9
- 230000000171 quenching effect Effects 0.000 claims description 9
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 8
- 150000001299 aldehydes Chemical class 0.000 claims description 8
- 239000000806 elastomer Substances 0.000 claims description 8
- 150000002148 esters Chemical class 0.000 claims description 8
- 150000002576 ketones Chemical class 0.000 claims description 8
- 150000008065 acid anhydrides Chemical class 0.000 claims description 7
- 239000006235 reinforcing carbon black Substances 0.000 claims description 7
- 238000001256 steam distillation Methods 0.000 claims description 7
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 claims description 6
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 claims description 6
- 150000001869 cobalt compounds Chemical class 0.000 claims description 6
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 5
- 239000011777 magnesium Substances 0.000 claims description 5
- 229910052749 magnesium Inorganic materials 0.000 claims description 5
- 229920003048 styrene butadiene rubber Polymers 0.000 claims description 5
- 125000006546 (C4-C10) cycloalkyl group Chemical group 0.000 claims description 4
- 239000002174 Styrene-butadiene Substances 0.000 claims description 4
- MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical compound C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000011115 styrene butadiene Substances 0.000 claims description 4
- 235000021355 Stearic acid Nutrition 0.000 claims description 3
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims description 3
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 claims description 3
- 239000008117 stearic acid Substances 0.000 claims description 3
- 150000003752 zinc compounds Chemical class 0.000 claims description 3
- 239000011787 zinc oxide Substances 0.000 claims description 3
- 229920001169 thermoplastic Polymers 0.000 claims description 2
- 239000004416 thermosoftening plastic Substances 0.000 claims description 2
- 229920000647 polyepoxide Polymers 0.000 claims 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 238000002955 isolation Methods 0.000 claims 1
- 239000000178 monomer Substances 0.000 abstract description 25
- 229910052779 Neodymium Inorganic materials 0.000 description 73
- QEFYFXOXNSNQGX-UHFFFAOYSA-N neodymium atom Chemical compound [Nd] QEFYFXOXNSNQGX-UHFFFAOYSA-N 0.000 description 67
- 125000001183 hydrocarbyl group Chemical group 0.000 description 30
- 238000002156 mixing Methods 0.000 description 28
- 239000002904 solvent Substances 0.000 description 26
- 239000003960 organic solvent Substances 0.000 description 24
- 239000003921 oil Substances 0.000 description 22
- 235000019198 oils Nutrition 0.000 description 22
- ACVYVLVWPXVTIT-UHFFFAOYSA-M phosphinate Chemical compound [O-][PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-M 0.000 description 21
- 239000006229 carbon black Substances 0.000 description 19
- 235000019241 carbon black Nutrition 0.000 description 19
- 238000006116 polymerization reaction Methods 0.000 description 19
- 229910052717 sulfur Inorganic materials 0.000 description 17
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
- 150000001298 alcohols Chemical class 0.000 description 14
- 239000007822 coupling agent Substances 0.000 description 14
- 239000000243 solution Substances 0.000 description 14
- 239000011593 sulfur Substances 0.000 description 14
- 229930195733 hydrocarbon Natural products 0.000 description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- 125000000392 cycloalkenyl group Chemical group 0.000 description 12
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 11
- 239000004594 Masterbatch (MB) Substances 0.000 description 10
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 10
- YNLAOSYQHBDIKW-UHFFFAOYSA-M diethylaluminium chloride Chemical compound CC[Al](Cl)CC YNLAOSYQHBDIKW-UHFFFAOYSA-M 0.000 description 10
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 9
- 239000004215 Carbon black (E152) Substances 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 229910052801 chlorine Inorganic materials 0.000 description 9
- 239000000470 constituent Substances 0.000 description 9
- AFABGHUZZDYHJO-UHFFFAOYSA-N dimethyl butane Natural products CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 9
- 125000005843 halogen group Chemical group 0.000 description 9
- 239000000463 material Substances 0.000 description 9
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- 125000000962 organic group Chemical group 0.000 description 9
- 241001441571 Hiodontidae Species 0.000 description 8
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 8
- 239000000460 chlorine Substances 0.000 description 8
- 125000005842 heteroatom Chemical group 0.000 description 8
- 229920005989 resin Polymers 0.000 description 8
- 239000011347 resin Substances 0.000 description 8
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 7
- 229910019142 PO4 Inorganic materials 0.000 description 7
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 7
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 7
- 125000004429 atom Chemical group 0.000 description 7
- 150000001993 dienes Chemical class 0.000 description 7
- 238000005227 gel permeation chromatography Methods 0.000 description 7
- 150000004820 halides Chemical class 0.000 description 7
- QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 description 7
- 150000002681 magnesium compounds Chemical class 0.000 description 7
- 238000005259 measurement Methods 0.000 description 7
- 239000002245 particle Substances 0.000 description 7
- 239000003208 petroleum Substances 0.000 description 7
- 235000021317 phosphate Nutrition 0.000 description 7
- 125000004437 phosphorous atom Chemical group 0.000 description 7
- LQIIEHBULBHJKX-UHFFFAOYSA-N 2-methylpropylalumane Chemical class CC(C)C[AlH2] LQIIEHBULBHJKX-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 125000003342 alkenyl group Chemical group 0.000 description 6
- 125000000304 alkynyl group Chemical group 0.000 description 6
- 125000003710 aryl alkyl group Chemical group 0.000 description 6
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 6
- 150000007942 carboxylates Chemical group 0.000 description 6
- 125000000753 cycloalkyl group Chemical group 0.000 description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
- 125000004430 oxygen atom Chemical group O* 0.000 description 6
- 125000003107 substituted aryl group Chemical group 0.000 description 6
- 125000005346 substituted cycloalkyl group Chemical group 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- LFXVBWRMVZPLFK-UHFFFAOYSA-N trioctylalumane Chemical compound CCCCCCCC[Al](CCCCCCCC)CCCCCCCC LFXVBWRMVZPLFK-UHFFFAOYSA-N 0.000 description 6
- OBETXYAYXDNJHR-UHFFFAOYSA-N 2-Ethylhexanoic acid Chemical compound CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 5
- GBQYMXVQHATSCC-UHFFFAOYSA-N 3-triethoxysilylpropanenitrile Chemical compound CCO[Si](OCC)(OCC)CCC#N GBQYMXVQHATSCC-UHFFFAOYSA-N 0.000 description 5
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 5
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 5
- 230000032683 aging Effects 0.000 description 5
- SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- MGDOJPNDRJNJBK-UHFFFAOYSA-N ethylaluminum Chemical compound [Al].C[CH2] MGDOJPNDRJNJBK-UHFFFAOYSA-N 0.000 description 5
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 5
- 150000002430 hydrocarbons Chemical class 0.000 description 5
- CPOFMOWDMVWCLF-UHFFFAOYSA-N methyl(oxo)alumane Chemical compound C[Al]=O CPOFMOWDMVWCLF-UHFFFAOYSA-N 0.000 description 5
- NRQNMMBQPIGPTB-UHFFFAOYSA-N methylaluminum Chemical compound [CH3].[Al] NRQNMMBQPIGPTB-UHFFFAOYSA-N 0.000 description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 description 5
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 5
- 150000002901 organomagnesium compounds Chemical class 0.000 description 5
- 230000003647 oxidation Effects 0.000 description 5
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- 239000000126 substance Substances 0.000 description 5
- 125000004434 sulfur atom Chemical group 0.000 description 5
- QQQSFSZALRVCSZ-UHFFFAOYSA-N triethoxysilane Chemical compound CCO[SiH](OCC)OCC QQQSFSZALRVCSZ-UHFFFAOYSA-N 0.000 description 5
- KVNYFPKFSJIPBJ-UHFFFAOYSA-N 1,2-diethylbenzene Chemical compound CCC1=CC=CC=C1CC KVNYFPKFSJIPBJ-UHFFFAOYSA-N 0.000 description 4
- ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 2,3-dimethylbutane Chemical compound CC(C)C(C)C ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 0.000 description 4
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 4
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- 239000002879 Lewis base Substances 0.000 description 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- VEQPNABPJHWNSG-UHFFFAOYSA-N Nickel(2+) Chemical compound [Ni+2] VEQPNABPJHWNSG-UHFFFAOYSA-N 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- 150000004703 alkoxides Chemical group 0.000 description 4
- 125000005234 alkyl aluminium group Chemical group 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 150000001868 cobalt Chemical class 0.000 description 4
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 4
- ZXPDYFSTVHQQOI-UHFFFAOYSA-N diethoxysilane Chemical compound CCO[SiH2]OCC ZXPDYFSTVHQQOI-UHFFFAOYSA-N 0.000 description 4
- ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- 150000007527 lewis bases Chemical class 0.000 description 4
- 229910001512 metal fluoride Inorganic materials 0.000 description 4
- 229910001507 metal halide Inorganic materials 0.000 description 4
- 150000005309 metal halides Chemical class 0.000 description 4
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 4
- GDOPTJXRTPNYNR-UHFFFAOYSA-N methylcyclopentane Chemical compound CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 description 4
- BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 4
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 4
- 125000001117 oleyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 4
- 239000010452 phosphate Substances 0.000 description 4
- 230000000379 polymerizing effect Effects 0.000 description 4
- 239000012991 xanthate Substances 0.000 description 4
- BHHYHSUAOQUXJK-UHFFFAOYSA-L zinc fluoride Chemical compound F[Zn]F BHHYHSUAOQUXJK-UHFFFAOYSA-L 0.000 description 4
- OWRCNXZUPFZXOS-UHFFFAOYSA-N 1,3-diphenylguanidine Chemical compound C=1C=CC=CC=1NC(=N)NC1=CC=CC=C1 OWRCNXZUPFZXOS-UHFFFAOYSA-N 0.000 description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 229910015900 BF3 Inorganic materials 0.000 description 3
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 3
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 3
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical class OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 3
- 238000004220 aggregation Methods 0.000 description 3
- 230000002776 aggregation Effects 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminum chloride Substances Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 3
- 125000000129 anionic group Chemical group 0.000 description 3
- 150000001450 anions Chemical class 0.000 description 3
- 229910052796 boron Inorganic materials 0.000 description 3
- SHZIWNPUGXLXDT-UHFFFAOYSA-N caproic acid ethyl ester Natural products CCCCCC(=O)OCC SHZIWNPUGXLXDT-UHFFFAOYSA-N 0.000 description 3
- 239000006231 channel black Substances 0.000 description 3
- 229920006026 co-polymeric resin Polymers 0.000 description 3
- OTARVPUIYXHRRB-UHFFFAOYSA-N diethoxy-methyl-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](C)(OCC)CCCOCC1CO1 OTARVPUIYXHRRB-UHFFFAOYSA-N 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- UAIZDWNSWGTKFZ-UHFFFAOYSA-L ethylaluminum(2+);dichloride Chemical compound CC[Al](Cl)Cl UAIZDWNSWGTKFZ-UHFFFAOYSA-L 0.000 description 3
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical class CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 3
- 229920001519 homopolymer Polymers 0.000 description 3
- 125000000743 hydrocarbylene group Chemical group 0.000 description 3
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 3
- 230000006872 improvement Effects 0.000 description 3
- 239000003999 initiator Substances 0.000 description 3
- 230000003993 interaction Effects 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- 239000011630 iodine Substances 0.000 description 3
- RLAWWYSOJDYHDC-BZSNNMDCSA-N lisinopril Chemical compound C([C@H](N[C@@H](CCCCN)C(=O)N1[C@@H](CCC1)C(O)=O)C(O)=O)CC1=CC=CC=C1 RLAWWYSOJDYHDC-BZSNNMDCSA-N 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
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- CGIHOAGHLXZIJX-UHFFFAOYSA-L dioctyl phosphate;nickel(2+) Chemical compound [Ni+2].CCCCCCCCOP([O-])(=O)OCCCCCCCC.CCCCCCCCOP([O-])(=O)OCCCCCCCC CGIHOAGHLXZIJX-UHFFFAOYSA-L 0.000 description 1
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- FNEMAUGFKGRJAJ-UHFFFAOYSA-H dioxido-oxo-phenyl-lambda5-phosphane neodymium(3+) Chemical compound [Nd+3].C1(=CC=CC=C1)P([O-])([O-])=O.C1(=CC=CC=C1)P([O-])([O-])=O.C1(=CC=CC=C1)P([O-])([O-])=O.[Nd+3] FNEMAUGFKGRJAJ-UHFFFAOYSA-H 0.000 description 1
- FCULJJOWPNXTTG-UHFFFAOYSA-L dipentyl phosphate;nickel(2+) Chemical compound [Ni+2].CCCCCOP([O-])(=O)OCCCCC.CCCCCOP([O-])(=O)OCCCCC FCULJJOWPNXTTG-UHFFFAOYSA-L 0.000 description 1
- BUHQQXGTFKPOJT-UHFFFAOYSA-K diphenyl phosphate;neodymium(3+) Chemical compound [Nd+3].C=1C=CC=CC=1OP(=O)([O-])OC1=CC=CC=C1.C=1C=CC=CC=1OP(=O)([O-])OC1=CC=CC=C1.C=1C=CC=CC=1OP(=O)([O-])OC1=CC=CC=C1 BUHQQXGTFKPOJT-UHFFFAOYSA-K 0.000 description 1
- RIARDECMAOPYBG-UHFFFAOYSA-L diphenyl phosphate;nickel(2+) Chemical compound [Ni+2].C=1C=CC=CC=1OP(=O)([O-])OC1=CC=CC=C1.C=1C=CC=CC=1OP(=O)([O-])OC1=CC=CC=C1 RIARDECMAOPYBG-UHFFFAOYSA-L 0.000 description 1
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- REMDLFHXTIFOIT-UHFFFAOYSA-K ethoxymethanedithioate neodymium(3+) Chemical compound [Nd+3].CCOC([S-])=S.CCOC([S-])=S.CCOC([S-])=S REMDLFHXTIFOIT-UHFFFAOYSA-K 0.000 description 1
- FHLLXKWLZMOECC-UHFFFAOYSA-N ethoxymethanedithioic acid;nickel Chemical compound [Ni].CCOC(S)=S FHLLXKWLZMOECC-UHFFFAOYSA-N 0.000 description 1
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- CSJWBNAOYWNTBI-UHFFFAOYSA-N ethyl-dimethoxy-[2-(oxiran-2-ylmethoxy)ethyl]silane Chemical compound CC[Si](OC)(OC)CCOCC1CO1 CSJWBNAOYWNTBI-UHFFFAOYSA-N 0.000 description 1
- YYDBOMXUCPLLSK-UHFFFAOYSA-N ethyl-dimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CC[Si](OC)(OC)CCCOCC1CO1 YYDBOMXUCPLLSK-UHFFFAOYSA-N 0.000 description 1
- BBIDBFWZMCTRNP-UHFFFAOYSA-N ethylalumane Chemical class CC[AlH2] BBIDBFWZMCTRNP-UHFFFAOYSA-N 0.000 description 1
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- OGPBJKLSAFTDLK-UHFFFAOYSA-N europium atom Chemical compound [Eu] OGPBJKLSAFTDLK-UHFFFAOYSA-N 0.000 description 1
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- 230000002349 favourable effect Effects 0.000 description 1
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- UPWPDUACHOATKO-UHFFFAOYSA-K gallium trichloride Chemical compound Cl[Ga](Cl)Cl UPWPDUACHOATKO-UHFFFAOYSA-K 0.000 description 1
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- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
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- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
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- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
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- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
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- 239000011261 inert gas Substances 0.000 description 1
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- PDJAZCSYYQODQF-UHFFFAOYSA-N iodine monofluoride Chemical compound IF PDJAZCSYYQODQF-UHFFFAOYSA-N 0.000 description 1
- VJUJMLSNVYZCDT-UHFFFAOYSA-N iodine trifluoride Chemical compound FI(F)F VJUJMLSNVYZCDT-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
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- 239000003446 ligand Substances 0.000 description 1
- 239000000944 linseed oil Substances 0.000 description 1
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- 239000007788 liquid Substances 0.000 description 1
- OHSVLFRHMCKCQY-UHFFFAOYSA-N lutetium atom Chemical compound [Lu] OHSVLFRHMCKCQY-UHFFFAOYSA-N 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
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- WRYKIHMRDIOPSI-UHFFFAOYSA-N magnesium;benzene Chemical compound [Mg+2].C1=CC=[C-]C=C1.C1=CC=[C-]C=C1 WRYKIHMRDIOPSI-UHFFFAOYSA-N 0.000 description 1
- KJJBSBKRXUVBMX-UHFFFAOYSA-N magnesium;butane Chemical compound [Mg+2].CCC[CH2-].CCC[CH2-] KJJBSBKRXUVBMX-UHFFFAOYSA-N 0.000 description 1
- VXWPONVCMVLXBW-UHFFFAOYSA-M magnesium;carbanide;iodide Chemical compound [CH3-].[Mg+2].[I-] VXWPONVCMVLXBW-UHFFFAOYSA-M 0.000 description 1
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- LZFCBBSYZJPPIV-UHFFFAOYSA-M magnesium;hexane;bromide Chemical compound [Mg+2].[Br-].CCCCC[CH2-] LZFCBBSYZJPPIV-UHFFFAOYSA-M 0.000 description 1
- GBRJQTLHXWRDOV-UHFFFAOYSA-M magnesium;hexane;chloride Chemical compound [Mg+2].[Cl-].CCCCC[CH2-] GBRJQTLHXWRDOV-UHFFFAOYSA-M 0.000 description 1
- WCFJMDWWJOCLSJ-UHFFFAOYSA-N magnesium;methanidylbenzene Chemical compound [Mg+2].[CH2-]C1=CC=CC=C1.[CH2-]C1=CC=CC=C1 WCFJMDWWJOCLSJ-UHFFFAOYSA-N 0.000 description 1
- QGEFGPVWRJCFQP-UHFFFAOYSA-M magnesium;methanidylbenzene;bromide Chemical compound [Mg+2].[Br-].[CH2-]C1=CC=CC=C1 QGEFGPVWRJCFQP-UHFFFAOYSA-M 0.000 description 1
- DQZLQYHGCKLKGU-UHFFFAOYSA-N magnesium;propane Chemical compound [Mg+2].C[CH-]C.C[CH-]C DQZLQYHGCKLKGU-UHFFFAOYSA-N 0.000 description 1
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- QQHNGZNHRRLNKI-UHFFFAOYSA-N methyl carbonobromidate Chemical compound COC(Br)=O QQHNGZNHRRLNKI-UHFFFAOYSA-N 0.000 description 1
- YGJMWVCEUNWDOU-UHFFFAOYSA-N methyl carbonofluoridate Chemical compound COC(F)=O YGJMWVCEUNWDOU-UHFFFAOYSA-N 0.000 description 1
- XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 1
- 239000005055 methyl trichlorosilane Substances 0.000 description 1
- XBKBZMOLSULOEA-UHFFFAOYSA-L methylaluminum(2+);dibromide Chemical compound C[Al](Br)Br XBKBZMOLSULOEA-UHFFFAOYSA-L 0.000 description 1
- FCUCJXXFUVRUTR-UHFFFAOYSA-L methylaluminum(2+);diphenoxide Chemical compound [Al+2]C.[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1 FCUCJXXFUVRUTR-UHFFFAOYSA-L 0.000 description 1
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- IDIGCVOPRGKSDP-UHFFFAOYSA-K neodymium(3+) phenylmethoxymethanedithioate Chemical compound [Nd+3].[S-]C(=S)OCc1ccccc1.[S-]C(=S)OCc1ccccc1.[S-]C(=S)OCc1ccccc1 IDIGCVOPRGKSDP-UHFFFAOYSA-K 0.000 description 1
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- HCOLBMWNEVUKDB-UHFFFAOYSA-K neodymium(3+) trithiocyanate Chemical compound [Nd+3].[S-]C#N.[S-]C#N.[S-]C#N HCOLBMWNEVUKDB-UHFFFAOYSA-K 0.000 description 1
- MPKWOMQKNIDCKY-UHFFFAOYSA-K neodymium(3+);2-nonylphenolate Chemical compound [Nd+3].CCCCCCCCCC1=CC=CC=C1[O-].CCCCCCCCCC1=CC=CC=C1[O-].CCCCCCCCCC1=CC=CC=C1[O-] MPKWOMQKNIDCKY-UHFFFAOYSA-K 0.000 description 1
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- HZHUIQPXRWTHNF-UHFFFAOYSA-N neodymium(3+);propan-2-olate Chemical compound [Nd+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] HZHUIQPXRWTHNF-UHFFFAOYSA-N 0.000 description 1
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- AARCLZBTVAUMJK-UHFFFAOYSA-K neodymium(3+);triformate Chemical compound [Nd+3].[O-]C=O.[O-]C=O.[O-]C=O AARCLZBTVAUMJK-UHFFFAOYSA-K 0.000 description 1
- TZNZEEADHYGQQO-UHFFFAOYSA-K neodymium(3+);triphenoxide Chemical compound [Nd+3].[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1 TZNZEEADHYGQQO-UHFFFAOYSA-K 0.000 description 1
- ATINCSYRHURBSP-UHFFFAOYSA-K neodymium(iii) chloride Chemical compound Cl[Nd](Cl)Cl ATINCSYRHURBSP-UHFFFAOYSA-K 0.000 description 1
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- JRUBGUVYQMKOMK-UHFFFAOYSA-N nickel(2+) diazide Chemical compound [Ni+2].[N-]=[N+]=[N-].[N-]=[N+]=[N-] JRUBGUVYQMKOMK-UHFFFAOYSA-N 0.000 description 1
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- CHPLEWYRKUFKQP-UHFFFAOYSA-N nickel(2+);1,2,3,5,5-pentamethylcyclopenta-1,3-diene Chemical compound [Ni+2].CC1=[C-]C(C)(C)C(C)=C1C.CC1=[C-]C(C)(C)C(C)=C1C CHPLEWYRKUFKQP-UHFFFAOYSA-N 0.000 description 1
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- JMWUYEFBFUCSAK-UHFFFAOYSA-L nickel(2+);octadecanoate Chemical compound [Ni+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O JMWUYEFBFUCSAK-UHFFFAOYSA-L 0.000 description 1
- DOLZKNFSRCEOFV-UHFFFAOYSA-L nickel(2+);oxalate Chemical compound [Ni+2].[O-]C(=O)C([O-])=O DOLZKNFSRCEOFV-UHFFFAOYSA-L 0.000 description 1
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- FLESAADTDNKLFJ-UHFFFAOYSA-N nickel;pentane-2,4-dione Chemical compound [Ni].CC(=O)CC(C)=O FLESAADTDNKLFJ-UHFFFAOYSA-N 0.000 description 1
- CKKFIFWNJHNWFE-UHFFFAOYSA-N nickel;pyridine-2-carboxylic acid Chemical compound [Ni].OC(=O)C1=CC=CC=N1 CKKFIFWNJHNWFE-UHFFFAOYSA-N 0.000 description 1
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- WIKDURKPSJEWGB-UHFFFAOYSA-N phenylmethoxymethanedithioic acid Chemical compound SC(=S)OCC1=CC=CC=C1 WIKDURKPSJEWGB-UHFFFAOYSA-N 0.000 description 1
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- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
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- VTQZBGAODFEJOW-UHFFFAOYSA-N selenium tetrabromide Chemical compound Br[Se](Br)(Br)Br VTQZBGAODFEJOW-UHFFFAOYSA-N 0.000 description 1
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- MCWWHQMTJNSXPX-UHFFFAOYSA-N tribenzylalumane Chemical compound C=1C=CC=CC=1C[Al](CC=1C=CC=CC=1)CC1=CC=CC=C1 MCWWHQMTJNSXPX-UHFFFAOYSA-N 0.000 description 1
- JKNHZOAONLKYQL-UHFFFAOYSA-K tribromoindigane Chemical compound Br[In](Br)Br JKNHZOAONLKYQL-UHFFFAOYSA-K 0.000 description 1
- DFNPRTKVCGZMMC-UHFFFAOYSA-M tributyl(fluoro)stannane Chemical compound CCCC[Sn](F)(CCCC)CCCC DFNPRTKVCGZMMC-UHFFFAOYSA-M 0.000 description 1
- FVRKTAOFDKFAMI-UHFFFAOYSA-M tributylstannanylium;bromide Chemical compound [Br-].CCCC[Sn+](CCCC)CCCC FVRKTAOFDKFAMI-UHFFFAOYSA-M 0.000 description 1
- ORVMIVQULIKXCP-UHFFFAOYSA-N trichloro(phenyl)silane Chemical compound Cl[Si](Cl)(Cl)C1=CC=CC=C1 ORVMIVQULIKXCP-UHFFFAOYSA-N 0.000 description 1
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- ZIYNWDQDHKSRCE-UHFFFAOYSA-N tricyclohexylalumane Chemical compound C1CCCCC1[Al](C1CCCCC1)C1CCCCC1 ZIYNWDQDHKSRCE-UHFFFAOYSA-N 0.000 description 1
- XBEXIHMRFRFRAM-UHFFFAOYSA-N tridodecylalumane Chemical compound CCCCCCCCCCCC[Al](CCCCCCCCCCCC)CCCCCCCCCCCC XBEXIHMRFRFRAM-UHFFFAOYSA-N 0.000 description 1
- FBBATURSCRIBHN-UHFFFAOYSA-N triethoxy-[3-(3-triethoxysilylpropyldisulfanyl)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCSSCCC[Si](OCC)(OCC)OCC FBBATURSCRIBHN-UHFFFAOYSA-N 0.000 description 1
- JXUKBNICSRJFAP-UHFFFAOYSA-N triethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCOCC1CO1 JXUKBNICSRJFAP-UHFFFAOYSA-N 0.000 description 1
- VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 description 1
- KQPIFPBKXYBDGV-UHFFFAOYSA-M triethylstannanylium;bromide Chemical compound CC[Sn](Br)(CC)CC KQPIFPBKXYBDGV-UHFFFAOYSA-M 0.000 description 1
- DFUIOHBANYCFQQ-UHFFFAOYSA-M triethylstannanylium;fluoride Chemical compound CC[Sn](F)(CC)CC DFUIOHBANYCFQQ-UHFFFAOYSA-M 0.000 description 1
- BHOCBLDBJFCBQS-UHFFFAOYSA-N trifluoro(methyl)silane Chemical compound C[Si](F)(F)F BHOCBLDBJFCBQS-UHFFFAOYSA-N 0.000 description 1
- KGWNTHHPMKEAIK-UHFFFAOYSA-N trifluoro(phenyl)silane Chemical compound F[Si](F)(F)C1=CC=CC=C1 KGWNTHHPMKEAIK-UHFFFAOYSA-N 0.000 description 1
- XRADHEAKQRNYQQ-UHFFFAOYSA-K trifluoroneodymium Chemical compound F[Nd](F)F XRADHEAKQRNYQQ-UHFFFAOYSA-K 0.000 description 1
- ORYGRKHDLWYTKX-UHFFFAOYSA-N trihexylalumane Chemical compound CCCCCC[Al](CCCCCC)CCCCCC ORYGRKHDLWYTKX-UHFFFAOYSA-N 0.000 description 1
- RMUKCGUDVKEQPL-UHFFFAOYSA-K triiodoindigane Chemical compound I[In](I)I RMUKCGUDVKEQPL-UHFFFAOYSA-K 0.000 description 1
- MCULRUJILOGHCJ-UHFFFAOYSA-N triisobutylaluminium Chemical compound CC(C)C[Al](CC(C)C)CC(C)C MCULRUJILOGHCJ-UHFFFAOYSA-N 0.000 description 1
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 1
- 239000005051 trimethylchlorosilane Substances 0.000 description 1
- MZGUIAFRJWSYJJ-UHFFFAOYSA-M trimethylstannanylium;bromide Chemical compound C[Sn](C)(C)Br MZGUIAFRJWSYJJ-UHFFFAOYSA-M 0.000 description 1
- YYPUUFWMUHDIRL-UHFFFAOYSA-M trimethylstannanylium;fluoride Chemical compound C[Sn](C)(C)F YYPUUFWMUHDIRL-UHFFFAOYSA-M 0.000 description 1
- JOJQVUCWSDRWJE-UHFFFAOYSA-N tripentylalumane Chemical compound CCCCC[Al](CCCCC)CCCCC JOJQVUCWSDRWJE-UHFFFAOYSA-N 0.000 description 1
- JQPMDTQDAXRDGS-UHFFFAOYSA-N triphenylalumane Chemical compound C1=CC=CC=C1[Al](C=1C=CC=CC=1)C1=CC=CC=C1 JQPMDTQDAXRDGS-UHFFFAOYSA-N 0.000 description 1
- JBWKIWSBJXDJDT-UHFFFAOYSA-N triphenylmethyl chloride Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(Cl)C1=CC=CC=C1 JBWKIWSBJXDJDT-UHFFFAOYSA-N 0.000 description 1
- CNWZYDSEVLFSMS-UHFFFAOYSA-N tripropylalumane Chemical compound CCC[Al](CCC)CCC CNWZYDSEVLFSMS-UHFFFAOYSA-N 0.000 description 1
- QDHQENQYSFSSQA-UHFFFAOYSA-N tris(1-methylcyclopentyl)alumane Chemical compound C1CCCC1(C)[Al](C1(C)CCCC1)C1(C)CCCC1 QDHQENQYSFSSQA-UHFFFAOYSA-N 0.000 description 1
- MYWRONRUDLXRGX-UHFFFAOYSA-N tris(2,2-dimethylpropyl)alumane Chemical compound CC(C)(C)C[Al](CC(C)(C)C)CC(C)(C)C MYWRONRUDLXRGX-UHFFFAOYSA-N 0.000 description 1
- ZHRAFNQICZNWIK-UHFFFAOYSA-N tris(2,6-dimethylphenyl)alumane Chemical compound CC1=CC=CC(C)=C1[Al](C=1C(=CC=CC=1C)C)C1=C(C)C=CC=C1C ZHRAFNQICZNWIK-UHFFFAOYSA-N 0.000 description 1
- FHAOCGKAMRAFMM-UHFFFAOYSA-N tris(2-ethylhexyl)alumane Chemical compound CCCCC(CC)C[Al](CC(CC)CCCC)CC(CC)CCCC FHAOCGKAMRAFMM-UHFFFAOYSA-N 0.000 description 1
- KBMBVTRWEAAZEY-UHFFFAOYSA-N trisulfane Chemical compound SSS KBMBVTRWEAAZEY-UHFFFAOYSA-N 0.000 description 1
- RTAKQLTYPVIOBZ-UHFFFAOYSA-N tritert-butylalumane Chemical compound CC(C)(C)[Al](C(C)(C)C)C(C)(C)C RTAKQLTYPVIOBZ-UHFFFAOYSA-N 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- VNDYJBBGRKZCSX-UHFFFAOYSA-L zinc bromide Chemical compound Br[Zn]Br VNDYJBBGRKZCSX-UHFFFAOYSA-L 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- BOXSVZNGTQTENJ-UHFFFAOYSA-L zinc dibutyldithiocarbamate Chemical compound [Zn+2].CCCCN(C([S-])=S)CCCC.CCCCN(C([S-])=S)CCCC BOXSVZNGTQTENJ-UHFFFAOYSA-L 0.000 description 1
- UAYWVJHJZHQCIE-UHFFFAOYSA-L zinc iodide Chemical compound I[Zn]I UAYWVJHJZHQCIE-UHFFFAOYSA-L 0.000 description 1
Classifications
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F4/00—Polymerisation catalysts
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- C08F4/44—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides
- C08F4/54—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides together with other compounds thereof
- C08F4/545—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides together with other compounds thereof rare earths being present, e.g. triethylaluminium + neodymium octanoate
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Abstract
Description
定義
変性高シスポリブタジエンポリマーの調製方法
触媒系
ランタニド系触媒系
ニッケル系触媒系
コバルト系触媒系
R5 pAlXq
式中、R5はC2~C12アルキル基であり、Xはハロゲンであり、p+qは3である。
官能性化合物
安定化剤
R2 nSi(OR3)4-n
式中、R2は、C1~C20アルキル、C4~C10シクロアルキル、又はC5~C20芳香族基からなる群から選択され、好ましくは、C1~C10アルキル、C4~C6シクロアルキル、又はC6~C14芳香族基、より好ましくはC1~C6アルキル、C4~C6シクロアルキル、又はC6芳香族基からなる群から選択され、R3はR2と同じであっても異なっていてもよく、C1~C20アルキル、C4~C10シクロアルキル、又はC5~C20芳香族基から選択され、好ましくは、C1~C10アルキル、C4~C6シクロアルキル、又はC6~C14芳香族基、より好ましくはC1~C6アルキル、C4~C6シクロアルキル、又はC6芳香族基から選択され、nは1~3、好ましくは2~3、より好ましくは3の整数である。第1の実施形態のプロセスの特定の実施形態では、式(II)の安定化剤は、前述の好ましい基又は値から選択されるR2、R3及びnを有する。第1の実施形態のプロセスの他の実施形態では、式(II)の安定化剤は、前述のより好ましい基又は値から選択されるR2、R3及びnを有する。第1の実施形態のプロセスの特に好ましい実施形態では、安定化剤トリアルコキシ(アルキル)シラン(すなわち、上記のように、nは3であり、R2はアルキルである)は、オクチルトリエトキシシランが特に好ましい。安定化剤が利用される第1の実施形態の実施形態では、(C)の後であるが(D)の前に、すなわち、変性高シスポリブタジエンを単離する前に添加される。安定化剤の使用は、変性高シスポリブタジエンポリマーを組み込んだタイヤトレッドにおいて、改善されたスノー又は氷上性能をもたらす、変性高シスポリブタジエンポリマーの製造に有益であり得る。当業者には理解されるように、タイヤトレッドへの組み込み時のゴム組成物のスノー又は氷上性能は、ゴム組成物の-20℃におけるG’の値を測定することによって予測することができ、より高い値は好ましい性能を示す。
急冷剤
R4COOH
式中、R4はHから選択され、C1~C18アルキル、好ましくはHからなる群、及びC1~C10アルキルからなる群から選択され、より好ましくはC2~C7アルキルからなる群から選択される。第1の実施形態の特定の好ましい実施形態では、急冷剤は、2-エチルヘキサン酸又は酢酸、より好ましくは2-エチルヘキサン酸を含み、特定のそのような実施形態では、急冷剤は、2-エチルヘキサン酸からなる。
急冷剤が利用される第1の実施形態の実施形態では、プロセスにおいて利用される量は変化し得る。第1の実施形態の特定の実施形態では、急冷剤は、0.1:1~10:1(例えば、0.1:1、0.5:1、1:1、2:1、3:1、4:1、5:1、6:1、7:1、8:1、9:1又は10:1)、好ましくは0.1:1~5:1(例えば、0.1:1、0.5:1、1:1、2:1、3:1、4:1又は5:1)、より好ましくは0.5:1~2:1(例えば、0.5:1、1:1、1.5:1又は2:1)のモル比で使用され、急冷剤のモル、式(II)の安定化剤のモルに基づくモル比である。
変性高シスポリブタジエンポリマーの特性
変性高シスポリブタジエンポリマー含有タイヤ成分
他のゴム
充填剤
可塑剤
硬化パッケージ
他の成分
ゴム組成物の調製方法
一般的な重合手順
2安定化剤のモル比:ネオジム
3シス-1,4結合測定について上述したように、FTIRによって測定
4官能化化合物は、式(I)によらない
2安定化剤のモル比:ネオジム
3シス-1,4結合測定について上述したように、FTIRによって測定
4官能化化合物は、式(I)によらない
2ビス(トリエトキシシリルプロピル)ジスルフィド
3TBBS及びDPG
Claims (20)
- 変性高シスポリブタジエンポリマーを調製するためのプロセスであって、
A.触媒系を提供することであって、
a.ランタニド系触媒系であって、(i)ランタニド化合物、(ii)アルキル化剤、及び(iii)ハロゲン源を含むランタニド系触媒系であって、(iii)(i)、(ii)、又は(i)及び(ii)の両方によって任意に提供されてもよい、ランタニド系触媒系と、
b.ニッケル系触媒系であって、(i)任意選択的にアルコールと組み合わせたニッケル化合物、(ii)有機アルミニウム、有機マグネシウム、有機亜鉛化合物、又はこれらの組み合わせと、(iii)フッ素含有化合物又はこれらの錯体と、を含むニッケル系触媒系と、
c.(i)コバルト化合物、(ii)有機ハロゲン化アルミニウム、及び(iii)任意に水を含むコバルト系触媒系と、を含む、ことと、
B.(A)の触媒系を使用して、1,3-ブタジエンを重合させて、リビング末端を有するポリマー鎖を生成することと、
C.(B)からの前記リビング末端ポリマー鎖を、以下の式(I)を有する官能化化合物と反応させることであって、
R1は、C1~C20、好ましくはC1~C10、より好ましくはC1~C3のヒドロカルビレンから選択され、上記のそれぞれは、1つの不飽和炭素-炭素結合を任意に含有し、
各R’は、C1~C20アルコキシ、好ましくはC1~C10アルコキシ、より好ましくはC1~C6アルコキシ、最も好ましくはC1又はC2のアルコキシから選択され、
R’’は、C1~C20のアルキル又はC6~C20のアリール、好ましくはC1~C10のアルキル又はC6~C14のアリール、より好ましくはC1~C6のアルキル又はC6のアリールから選択され、
それにより、少なくとも92%、好ましくは少なくとも94%のシス1,4-結合含量を有する変性高シスポリブタジエンを生成する、ことと、
D.(C)の変性高シスポリブタジエンを単離して、最終変性高シスポリブタジエンを生成することであって、
100℃で20~100、好ましくは30~80の初期ムーニー粘度ML1+4であり、
100℃で120以下、好ましくは105以下の熟成ムーニー粘度ML1+4であり、
前記単離は、好ましくは、水蒸気蒸留によって行われる、ことと、を含む、プロセス。 - 前記官能化化合物が、モル比が官能化化合物の前記モル、前記触媒系の一次金属のモルを基準として100:1~0.5:1、好ましくは50:1~1:1、より好ましくは30:1~2:1の前記モル比で使用される、請求項1に記載のプロセス。
- 式(I)のXがエポキシ基であり、好ましくは、前記エポキシ環中に2~4個の炭素原子を有するエポキシ基である、請求項1又は2に記載のプロセス。
- 式(I)のXがグリシドキシ基である、請求項3に記載のプロセス。
- 式(I)のXがシアノ基である、請求項1又は2に記載のプロセス。
- (D)の前に、(C)の前記変性高シスポリブタジエンを、以下の式(II)の安定化剤と反応させることであって、
R2 nSi(OR3)4-n
式中、R2は、C1~C20アルキル、C4~C10シクロアルキル、又はC5~C20芳香族基からなる群から選択され、好ましくは、C1~C10アルキル、C4~C6シクロアルキル、又はC6~C14芳香族基、より好ましくはC1~C6アルキル、C4~C6シクロアルキル、又はC6芳香族基からなる群から選択され、
式中、R3はR2と同じであっても異なっていてもよく、C1~C20アルキル、C4~C10シクロアルキル、又はC5~C20芳香族基から選択され、好ましくは、C1~C10アルキル、C4~C6シクロアルキル、又はC6~C14芳香族基、より好ましくはC1~C6アルキル、C4~C6シクロアルキル、又はC6芳香族基からなる群から選択され、
nは1~3の整数である、ことを更に含む、請求項1~5のいずれか一項に記載のプロセス。 - 前記安定化剤が、安定化剤の前記モル、官能化化合物のモルを基準として、モル比が0.01:1~10:1、好ましくは0.1:1~5:1、より好ましくは0.5:1~2:1の前記モル比で使用される、請求項6に記載のプロセス。
- 前記安定化剤が、以下の式(III)の急冷剤と共に使用され、
R4COOH
式中、R4はH及びC1~C18アルキルからなる群から選択され、好ましくはH及びC1~C10アルキルからなる群から選択され、より好ましくはC2~C8アルキルからなる群から選択される、請求項6又は7に記載のプロセス。 - 式(III)の前記急冷剤が、モル比が急冷剤の前記モル、安定化剤のモルに基づいて前記モル比が0.1:1~10:1、好ましくは0.1:1~5:1、より好ましくは0.5:1~2:1で使用される、請求項8に記載のプロセス。
- 前記触媒系が、ランタニド系触媒系(a)である、請求項1~9のいずれか一項に記載のプロセス。
- 前記ポリブタジエンが、以下のうちの少なくとも1つを満たし、
a.150,000~2,000,000グラム/モル、好ましくは250,000~1,000,000グラム/モル、より好ましくは300,000~800,000グラム/モルのMwを有する、
b.80,000~800,000グラム/モル、好ましくは90,000~500,000グラム/モル、より好ましくは150,000~400,000グラム/モルのMnを有する、
c.1.5~4、好ましくは1.8~3.8、又は1.8~2.5のMw/Mnを有し、又は
d.100℃で40~70の初期ムーニー粘度ML1+4を有する、請求項1~10のいずれか一項に記載のプロセス。 - 請求項1~11のいずれか一項に記載のプロセスから得られる変性高シスポリブタジエンポリマー。
- 変性高シスポリブタジエンポリマーであって、
以下の式(I)を有する官能化化合物の残基に結合したポリマー鎖を有し、
R1は、C1~C20、好ましくはC1~C10、より好ましくはC1~C3のヒドロカルビレンから選択され、上記のそれぞれは、1つの不飽和炭素-炭素結合を任意に含有し、
各R’は、C1~C20アルコキシ、好ましくはC1~C10アルコキシ、より好ましくはC1~C6アルコキシ、最も好ましくはC1又はC2のアルコキシから選択され、
R’’は、C1~C20のアルキル又はC6~C20のアリール、好ましくはC1~C10のアルキル又はC6~C14のアリール、より好ましくはC1~C6のアルキル又はC6のアリールから選択され、
各ポリマー鎖が、前記X基を介して前記官能化化合物の前記残基に結合され、前記ポリマーが、
100℃で20~100、好ましくは30~80の初期ムーニー粘度ML1+4であり、
100Cで120以下、好ましくは105以下の熟成ムーニー粘度ML1+4である、変性高シスポリブタジエンポリマー。 - 以下のうちの少なくとも1つを満たす、請求項13に記載の高シス変性ポリブタジエンポリマーであって、
a.150,000~2,000,000グラム/モル、好ましくは250,000~1,000,000グラム/モル、より好ましくは300,000~800,000グラム/モルのMwを有し、
b.80,000~800,000グラム/モル、好ましくは90,000~500,000グラム/モル、より好ましくは150,000~400,000グラム/モルのMnを有し、
c.1.5~4、好ましくは1.8~3.8、又は1.8~2.5のMw/Mnを有し、又は
d.100℃で40~70の初期ムーニー粘度ML1+4を有する、請求項13に記載の高シス変性ポリブタジエンポリマー。 - (a)~(d)のそれぞれが満たされる、請求項14に記載の高シス変性ポリブタジエンポリマー。
- 式(I)のXがエポキシ基である、請求項13~15のいずれか一項に記載の高シス変性ポリブタジエンポリマー。
- 式(I)のXがグリシドキシ基であり、前記ポリマー鎖が、前記エポキシ基から炭素原子に結合している、請求項16に記載の高シス変性ポリブタジエンポリマー。
- 式(I)のXがシアノ基である、請求項13~15のいずれか一項に記載の高シス変性ポリブタジエンポリマー。
- ゴム組成物を含むタイヤ成分であって、
a.エラストマー成分であって、
i.10~100phr、好ましくは20~80phrの、請求項13~18のいずれか一項に記載の高シス変性ポリブタジエンポリマー又は請求項1~12のいずれか一項に記載のプロセスから得られる前記高シス変性ポリブタジエンポリマーと、
ii.0~90phrの、未変性ポリブタジエン、スチレン-ブタジエン、天然ゴム、ポリイソプレンからなる群から選択される少なくとも1つの追加のポリマーと、を含む、エラストマー成分と、
b.補強充填剤成分であって、
i.10~200phr、好ましくは30~200phr、より好ましくは50~150phrの補強シリカ充填剤と、
ii.0~50phrの補強カーボンブラック充填剤であって、前記補強カーボンブラック充填剤が、補強シリカ充填剤の重量の20%以下、好ましくは補強シリカ充填剤の重量の10%以下の量で存在する、補強カーボンブラック充填剤と、を含む、補強充填剤成分と、
c.可塑化成分であって、
i.0~50phr、好ましくは0~30phr、より好ましくは0~15phrの少なくとも1種の可塑化油と、
ii.0~60phr、好ましくは5~60phr、より好ましくは10~50phrの、少なくとも30℃のTgを有する少なくとも1つの炭化水素樹脂と、を含む、可塑化成分と、
d.硬化パッケージ(好ましくは、少なくとも1つの加硫剤;少なくとも1つの加硫促進剤;及び任意選択で加硫活性剤(例えば、酸化亜鉛、ステアリン酸など)、加硫抑制剤、及び/又は焦げ付き防止剤、より好ましくは、前述のそれぞれの少なくとも1つを含む)と、を含む、タイヤ成分。 - トレッドである、請求項19に記載のタイヤ成分。
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