JP2020041166A - 金属錯体触媒、それを使用した重合方法、及びそのポリマー生成物 - Google Patents
金属錯体触媒、それを使用した重合方法、及びそのポリマー生成物 Download PDFInfo
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- JP2020041166A JP2020041166A JP2019229141A JP2019229141A JP2020041166A JP 2020041166 A JP2020041166 A JP 2020041166A JP 2019229141 A JP2019229141 A JP 2019229141A JP 2019229141 A JP2019229141 A JP 2019229141A JP 2020041166 A JP2020041166 A JP 2020041166A
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- 150000002484 inorganic compounds Chemical class 0.000 description 1
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- 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
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- 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
- IWCVDCOJSPWGRW-UHFFFAOYSA-M magnesium;benzene;chloride Chemical compound [Mg+2].[Cl-].C1=CC=[C-]C=C1 IWCVDCOJSPWGRW-UHFFFAOYSA-M 0.000 description 1
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- 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
- 238000000386 microscopy Methods 0.000 description 1
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- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- JXRJZEIFKKYMBS-UHFFFAOYSA-N octyl(phenyl)alumane Chemical compound C1(=CC=CC=C1)[AlH]CCCCCCCC JXRJZEIFKKYMBS-UHFFFAOYSA-N 0.000 description 1
- KMKBWZXSKDYZDZ-UHFFFAOYSA-M octyl(phenyl)alumanylium;chloride Chemical compound [Cl-].CCCCCCCC[Al+]C1=CC=CC=C1 KMKBWZXSKDYZDZ-UHFFFAOYSA-M 0.000 description 1
- SOEVKJXMZBAALG-UHFFFAOYSA-N octylalumane Chemical compound CCCCCCCC[AlH2] SOEVKJXMZBAALG-UHFFFAOYSA-N 0.000 description 1
- RBLGTYCOUOIUNY-UHFFFAOYSA-L octylaluminum(2+);dichloride Chemical compound CCCCCCCC[Al](Cl)Cl RBLGTYCOUOIUNY-UHFFFAOYSA-L 0.000 description 1
- 238000000643 oven drying Methods 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-O oxonium Chemical compound [OH3+] XLYOFNOQVPJJNP-UHFFFAOYSA-O 0.000 description 1
- 239000010690 paraffinic oil Substances 0.000 description 1
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- QDUCABQBSRSYCO-UHFFFAOYSA-N phenyl(propan-2-yl)alumane Chemical compound C1(=CC=CC=C1)[AlH]C(C)C QDUCABQBSRSYCO-UHFFFAOYSA-N 0.000 description 1
- CUIJJJLOSZSJRO-UHFFFAOYSA-M phenyl(propan-2-yl)alumanylium;chloride Chemical compound [Cl-].CC(C)[Al+]C1=CC=CC=C1 CUIJJJLOSZSJRO-UHFFFAOYSA-M 0.000 description 1
- ZKGDHJAHOGRQEP-UHFFFAOYSA-N phenyl(propyl)alumane Chemical compound C1(=CC=CC=C1)[AlH]CCC ZKGDHJAHOGRQEP-UHFFFAOYSA-N 0.000 description 1
- AAQNAPUTWYBWOV-UHFFFAOYSA-M phenyl(propyl)alumanylium;chloride Chemical compound [Cl-].CCC[Al+]C1=CC=CC=C1 AAQNAPUTWYBWOV-UHFFFAOYSA-M 0.000 description 1
- ANRQGKOBLBYXFM-UHFFFAOYSA-M phenylmagnesium bromide Chemical compound Br[Mg]C1=CC=CC=C1 ANRQGKOBLBYXFM-UHFFFAOYSA-M 0.000 description 1
- 150000003003 phosphines Chemical class 0.000 description 1
- 125000004437 phosphorous atom Chemical group 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- DOIRQSBPFJWKBE-UHFFFAOYSA-N phthalic acid di-n-butyl ester Natural products CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 1
- 229910052615 phyllosilicate Inorganic materials 0.000 description 1
- 230000000704 physical effect Effects 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
- 229920002587 poly(1,3-butadiene) polymer Polymers 0.000 description 1
- 239000002685 polymerization catalyst Substances 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000005077 polysulfide Substances 0.000 description 1
- 229920001021 polysulfide Polymers 0.000 description 1
- 150000008117 polysulfides Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000012673 precipitation polymerization Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000011164 primary particle Substances 0.000 description 1
- 239000010734 process oil Substances 0.000 description 1
- ZYTJPPRBIGGXRO-UHFFFAOYSA-N propan-2-ylalumane Chemical compound C(C)(C)[AlH2] ZYTJPPRBIGGXRO-UHFFFAOYSA-N 0.000 description 1
- DXGIRFAFSFKYCF-UHFFFAOYSA-N propanehydrazide Chemical compound CCC(=O)NN DXGIRFAFSFKYCF-UHFFFAOYSA-N 0.000 description 1
- OBRKWFIGZSMARO-UHFFFAOYSA-N propylalumane Chemical compound [AlH2]CCC OBRKWFIGZSMARO-UHFFFAOYSA-N 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 150000004053 quinones Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000002787 reinforcement Effects 0.000 description 1
- 230000003014 reinforcing effect Effects 0.000 description 1
- 239000011342 resin composition Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910052706 scandium Inorganic materials 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000005372 silanol group Chemical group 0.000 description 1
- 229960004029 silicic acid Drugs 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 239000012798 spherical particle Substances 0.000 description 1
- 235000015096 spirit Nutrition 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 230000000707 stereoselective effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 125000005346 substituted cycloalkyl group Chemical group 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 238000010301 surface-oxidation reaction Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 1
- 125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- XBFJAVXCNXDMBH-UHFFFAOYSA-N tetracyclo[6.2.1.1(3,6).0(2,7)]dodec-4-ene Chemical compound C1C(C23)C=CC1C3C1CC2CC1 XBFJAVXCNXDMBH-UHFFFAOYSA-N 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 125000004665 trialkylsilyl group Chemical group 0.000 description 1
- 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
- SQBBHCOIQXKPHL-UHFFFAOYSA-N tributylalumane Chemical compound CCCC[Al](CCCC)CCCC SQBBHCOIQXKPHL-UHFFFAOYSA-N 0.000 description 1
- ZIYNWDQDHKSRCE-UHFFFAOYSA-N tricyclohexylalumane Chemical compound C1CCCCC1[Al](C1CCCCC1)C1CCCCC1 ZIYNWDQDHKSRCE-UHFFFAOYSA-N 0.000 description 1
- VTHOKNTVYKTUPI-UHFFFAOYSA-N triethoxy-[3-(3-triethoxysilylpropyltetrasulfanyl)propyl]silane Chemical group CCO[Si](OCC)(OCC)CCCSSSSCCC[Si](OCC)(OCC)OCC VTHOKNTVYKTUPI-UHFFFAOYSA-N 0.000 description 1
- VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 description 1
- ORYGRKHDLWYTKX-UHFFFAOYSA-N trihexylalumane Chemical compound CCCCCC[Al](CCCCCC)CCCCCC ORYGRKHDLWYTKX-UHFFFAOYSA-N 0.000 description 1
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 1
- LFXVBWRMVZPLFK-UHFFFAOYSA-N trioctylalumane Chemical compound CCCCCCCC[Al](CCCCCCCC)CCCCCCCC LFXVBWRMVZPLFK-UHFFFAOYSA-N 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
- 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
- GIIXTFIYICRGMZ-UHFFFAOYSA-N tris(2,3-dimethylphenyl)phosphane Chemical compound CC1=CC=CC(P(C=2C(=C(C)C=CC=2)C)C=2C(=C(C)C=CC=2)C)=C1C GIIXTFIYICRGMZ-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
- COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 1
- WSITXTIRYQMZHM-UHFFFAOYSA-N tris(4-methylphenyl)alumane Chemical compound C1=CC(C)=CC=C1[Al](C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 WSITXTIRYQMZHM-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
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000004073 vulcanization Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
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- 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
- C08F236/06—Butadiene
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- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F17/00—Metallocenes
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- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/10—Compounds having one or more C—Si linkages containing nitrogen having a Si-N linkage
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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- C08F210/00—Copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
- C08F210/02—Ethene
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F297/00—Macromolecular compounds obtained by successively polymerising different monomer systems using a catalyst of the ionic or coordination type without deactivating the intermediate polymer
- C08F297/06—Macromolecular compounds obtained by successively polymerising different monomer systems using a catalyst of the ionic or coordination type without deactivating the intermediate polymer using a catalyst of the coordination type
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- 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
- C08F4/00—Polymerisation catalysts
- C08F4/42—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors
- 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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- 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
- C08F4/00—Polymerisation catalysts
- C08F4/42—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors
- 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
- C08F4/60—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 refractory metals, iron group metals, platinum group metals, manganese, rhenium technetium or compounds thereof
- C08F4/62—Refractory metals or compounds thereof
- C08F4/639—Component covered by group C08F4/62 containing a transition metal-carbon bond
- C08F4/6392—Component covered by group C08F4/62 containing a transition metal-carbon bond containing at least one cyclopentadienyl ring, condensed or not, e.g. an indenyl or a fluorenyl ring
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- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L9/00—Compositions of homopolymers or copolymers of conjugated diene hydrocarbons
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- C08F2800/00—Copolymer characterised by the proportions of the comonomers expressed
- C08F2800/10—Copolymer characterised by the proportions of the comonomers expressed as molar percentages
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- C08F2810/00—Chemical modification of a polymer
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- Crystallography & Structural Chemistry (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Polymerization Catalysts (AREA)
Abstract
Description
本出願は2014年5月31日出願の米国特許仮出願第62/006,119号及び2015年3月20日出願の米国特許仮出願第62/136,302号の利益を主張し、これらの開示は参照により本明細書に組み込まれる。
式中、Mは第3族金属原子を表し、Lは中性ルイス塩基を表し、zは0及び3を含む0〜3の整数であり、mは1又は2であり、ただしm=2のときシリル基はインデニル配位子の1位及び3位にあり、nは1又は2であり、各R1は独立してH、ハロゲン原子、C1〜C20アルキル基、C5〜C8シクロアルキル基、アラルキル基、アルコキシ基、シロキシ基、ニトロ基、スルホネート基、又は−(CH2)yR3基であり、ここでyは0又は1であり、R3は置換若しくは非置換アリール基であり、R2はX型モノアニオン性配位子である。L基及びR2基は、それぞれが結合しているM原子と共に任意に結合して環状部分を提供することができる。代替的に又は追加的に、2つのR1基は結合して、置換又は非置換ヒドロカルビレン基を形成することができ、Si原子と一緒になって環状部分を形成することができる。
「ポリマー」とは1つ以上のモノマーの重合生成物を意味し、ホモポリマー、コポリマー、ターポリマー、テトラポリマーなどを含む。
「マー」及び「マー単位」は両方とも、1つの反応分子から生成されるポリマーの一部を意味する(例えばエチレンマーは一般式−CH2CH2−を有する)。
「コポリマー」は、2つの反応物質、通常はモノマーから生成されるマー単位を含んだポリマーを意味し、ランダム、ブロック、セグメント化、グラフトなどのコポリマーを含む。
「インターポリマー」は、少なくとも2つの反応物質、通常はモノマーから生成されるマー単位を含んだポリマーを意味し、コポリマー、ターポリマー、テトラポリマーなどを含む。
「置換」は、当該基の意図した目的を阻害しないヘテロ原子又は官能基(例えば、ヒドロカルビル基)を含むことを意味する。
「ポリエン」は、最長部分又はその鎖に少なくとも2つの二重結合が存在する分子、通常はモノマーを意味し、具体的にはジエン、トリエンなどを含む。
「ポリジエン」は、1つ以上のジエンのマー単位を含むポリマーを意味する。
「ランタノイド金属」とは、原子番号57及び71を含む57〜71の任意の元素を意味する。
「第3族金属」とは、Sc、Y又はランタノイド系金属を意味する。
「phr」とは、ゴム100重量部(pbw)当たりの重量部(pbw)を意味する。
「ラジカル」は、反応の結果、任意の原子が得られるか又は失われるかに関わらず、別の分子と反応した後に残る分子の一部を意味する。
「中性ルイス塩基」とは、一対の利用可能な電子を含む非イオン性化合物(又はラジカル)を意味する。
「アリール」とは、フェニル又は多環式芳香族ラジカルを意味する。
「アラルキル」とは、アリール置換基、例えばベンジル基を含有するアルキルラジカルを意味する。
「非配位アニオン」は、例えば立体障害により触媒系の活性中心と配位結合を形成しない立体的に嵩高なアニオンを意味する。
「非配位アニオン前駆体」は、反応条件下で非配位アニオンを形成することが可能な化合物を意味する。
「末端」とは、ポリマー鎖の端部を意味する。
「末端活性の」とは、リビング末端又は擬似リビング末端を有するポリマーを意味する。
「末端部分」は、末端に位置する基又は官能基を意味する。
トリメチルアルミニウム、トリエチルアルミニウム、トリイソブチルアルミニウム(TIBA)、トリ−n−プロピルアルミニウム、トリイソプロピルアルミニウム、トリ−n−ブチルアルミニウム、トリ−t−ブチルアルミニウム、トリ−n−ペンチルアルミニウム、トリネオペンチルアルミニウム、トリ−n−ヘキシルアルミニウム、トリ−n−オクチルアルミニウム、トリス(2−エチルヘキシル)アルミニウム、トリシクロヘキシルアルミニウム、トリス(1−メチルシクロペンチル)アルミニウム、トリフェニルアルミニウム、トリ−p−トリルアルミニウム、トリス(2,6−ジメチルフェニル)アルミニウム、トリベンジルアルミニウム、ジエチルフェニルアルミニウム、ジエチル−p−トリルアルミニウム、ジエチルベンジルアルミニウム、エチルジフェニルアルミニウム、エチルジ−p−トリルアルミニウム、及びエチルジベンジルアルミニウムなどのトリヒドロカルビルアルミニウム;
ジエチルアルミニウムヒドリド、ジ−n−プロピルアルミニウムヒドリド、ジイソプロピルアルミニウムヒドリド、ジ−n−ブチルアルミニウムヒドリド、ジイソブチルアルミニウムヒドリド(DIBAH)、ジ−n−オクチルアルミニウムヒドリド、ジフェニルアルミニウムヒドリド、ジ−p−トリルアルミニウムヒドリド、ジベンジルアルミニウムヒドリド、フェニルエチルアルミニウムヒドリド、フェニル−n−プロピルアルミニウムヒドリド、フェニルイソプロピルアルミニウムヒドリド、フェニル−n−ブチルアルミニウムヒドリド、フェニルイソブチルアルミニウムヒドリド、フェニル−n−オクチルアルミニウムヒドリド、p−トリルエチルアルミニウムヒドリド、p−トリル−n−プロピルアルミニウムヒドリド、p−トリイソプロピルアルミニウムヒドリド、p−トリル−n−ブチルアルミニウムヒドリド、p−トリイソブチルアルミニウムヒドリド、p−トリル−n−オクチルアルミニウムヒドリド、ベンジルエチルアルミニウムヒドリド、ベンジル−n−プロピルアルミニウムヒドリド、ベンジルイソプロピルアルミニウムヒドリド、ベンジル−n−ブチルアルミニウムヒドリド、ベンジルイソブチルアルミニウムヒドリド、及びベンジル−n−オクチルアルミニウムヒドリドなどのジヒドロカルビルアルミニウムヒドリド;
エチルアルミニウムジヒドリド、n−プロピルアルミニウムジヒドリド、イソプロピルアルミニウムジヒドリド、n−ブチルアルミニウムジヒドリド、イソブチルアルミニウムジヒドリド、及びn−オクチルアルミニウムジヒドリドなどのヒドロカルビルアルミニウムジヒドリド;
ジヒドロカルビルアルミニウムカルボキシレート;
ヒドロカルビルアルミニウムビス(カルボキシレート);
ジヒドロカルビルアルミニウムアルコキシド;
ヒドロカルビルアルミニウムジアルコキシド;
ジエチルアルミニウムクロリド(DEAC)、ジ−n−プロピルアルミニウムクロリド、ジイソプロピルアルミニウムクロリド、ジ−n−ブチルアルミニウムクロリド、ジイソブチルアルミニウムクロリド、ジ−n−オクチルアルミニウムクロリド、ジフェニルアルミニウムクロリド、ジ−p−トリルアルミニウムクロリド、ジベンジルアルミニウムクロリド、フェニルエチルアルミニウムクロリド、フェニル−n−プロピルアルミニウムクロリド、フェニルイソプロピルアルミニウムクロリド、フェニル−n−ブチルアルミニウムクロリド、フェニルイソブチルアルミニウムクロリド、フェニル−n−オクチルアルミニウムクロリド、p−トリルエチルアルミニウムクロリド、p−トリル−n−プロピルアルミニウムクロリド、p−トリイソプロピルアルミニウムクロリド、p−トリル−n−ブチルアルミニウムクロリド、p−トリイソブチルアルミニウムクロリド、p−トリル−n−オクチルアルミニウムクロリド、ベンジルエチルアルミニウムクロリド、ベンジル−n−プロピルアルミニウムクロリド、ベンジルイソプロピルアルミニウムクロリド、ベンジル−n−ブチルアルミニウムクロリド、ベンジルイソブチルアルミニウムクロリド、及びベンジル−n−オクチルアルミニウムクロリドなどのジヒドロカルビルアルミニウムハライド;
エチルアルミニウムジクロリド、n−プロピルアルミニウムジクロリド、イソプロピルアルミニウムジクロリド、n−ブチルアルミニウムジクロリド、イソブチルアルミニウムジクロリド、及びn−オクチルアルミニウムジクロリドなどのヒドロカルビルアルミニウムジハライド;
ジヒドロカルビルアルミニウムアリールオキシド;及び
ヒドロカルビルアルミニウムジアリールオキシドが、挙げられる。
アルキル化剤対式(I)の錯体は約1:1〜約1000:1、一般的には約2:1〜約500:1、通常は約5:1〜約200:1、
アルミノキサン対式(I)の錯体、特にアルミノキサンのアルミニウム原子当量対錯体の第3族原子当量は約5:1〜約1000:1、一般的には約10:1〜約700:1、通常は約20:1〜約500:1、
有機アルミニウム化合物対式(I)の錯体は約1:1〜約200:1、一般的には約2:1〜約150:1、通常は約5:1〜約100:1、及び
非配位性アニオン又は前駆体剤対式(I)の錯体は約1:2〜約20:1、一般的には約3:4〜約10:1、通常は約1:1〜約6:1である。
(1)その場で。触媒成分を、モノマー及び溶媒を含有する溶液(又は単にバルクモノマー)に添加する。添加は、段階的に又は同時に起こってもよい。後者の場合、アルキル化剤を好ましくは最初に添加して、式(I)の錯体が続いて加えられる。
(2)予混合。共役ジエンモノマーに導入する前に、成分を一般的には約−20℃〜約80℃の温度で重合系外で混合してもよい。
(3)モノマー(複数可)の存在下で予形成。触媒成分を少量の共役ジエンモノマー(複数可)の存在下で約−20℃〜約80℃の温度で混合する。モノマーの量は式(I)の錯体のモル当たり、約1〜約500モル、一般的には約5〜約250モル、通常は約10〜約100モルの範囲であり得る。得られる触媒組成物は、重合されるモノマーの残りに添加される。
(4)2段階処理。
(a)アルキル化剤を約−20℃〜約80℃の温度で、モノマーの不存在下で又は少量のモノマー(複数可)の存在下で式(I)の錯体と混合する。
(b)前述の混合物及び残留成分を、重合されるモノマー(複数可)の残りに段階的又は同時に添加する。
1−tert−ブチルジメチルシリルインデン、1,3−ビス(トリメチルシリル)インデン及び1,3−ビス(tert−ブチルジメチルシリル)インデン:A.Davison et al,J.Organomet.Chem.,23(2),pp.407〜26(1970)and C.A.Bradley et al,Organometallics,23,pp.5332〜46(2004)、
ガドリニウム(III)トリス[N,N−ビス(トリメチルシリル)アミド]:D.C.Bradley et al.,J.Chem.Soc.,Chem.Commun.pp.349〜50(1972)、
ジ(オクタデシル)メチルアンモニウムテトラキス(ペンタフルオロフェニル)ボレート:米国特許第5,919,983号(Rosenら)。
Ar流下で冷却したオーブン乾燥した500mLのシュレンク管に200mLの乾燥THFを、続いて1.64g(14.1mmol)のインデンを加えた。この溶液を−78℃で冷却して、n−ブチルリチウムの1.55Mヘキサン溶液9.29mLを約5分間かけて滴下した。内容物をこの温度で約10分間攪拌した。
Ar流下で冷却したオーブン乾燥した500mLのシュレンク管に200mLの乾燥THFを、続いて3.0g(25.8mmol)のインデンを加えた。この溶液を−78℃で冷却して、n−ブチルリチウムの1.55Mヘキサン溶液16.9mLを約5分間かけて滴下した。内容物をこの温度で約10分間攪拌した。
Ar下で、実施例1aで調製された化合物(0.627g、1.5mmol)の15mLヘキサン溶液を、1.00g(1.6mmol)のGd(III){N[Si(CH3)3]2}3のヘキサン溶液(以下「Gd[N(TMS)2]3」とする)15mLに滴加した。この混合物を一晩80℃で撹拌し(約14時間)、その間、黄色溶液が形成された。
Ar下で、ヘキサン中の実施例1bで調製された化合物(1.22g、4.6mmol)及び1.50g(2.35mmol)のGd[N(TMS)2]3の30mL溶液を、2.22mLの1,1,3,3−テトラメチルジシラザン(1.25g、12.5mmol)にゆっくりと添加した。少量の白色沈殿物が速やかに形成された。
Ar下で、ヘキサン中の1−tert−ブチルジメチルシリルインデン(1.415g、6.1mmol)及び2.00g(3.1mmol)のGd[N(TMS)2]3の30mL溶液を、2.22mLの1,1,3,3−テトラメチルジシラザン(1.67g、12.5mmol)にゆっくりと添加した。少量の白色沈殿物が速やかに形成された。
2.116g(6.1mmol)の1,3−ビス(tert−ブチルジメチルシリル)インデンが1−tert−ブチルジメチルシリルインデンの代わりに使われたこと以外は、実施例2cの反応を繰り返した。
1.600g(6.1mmol)の1,3−ビス(トリメチルシリル)インデンが1,3−ビス(tert−ブチルジメチルシリル)インデンの代わりに使われたこと以外は、実施例2dのプロセスを繰り返した。回収された生成物は、2.46g(約99%収率)の黄色油状物であった。
上述と類似の手順を用いて、以下の追加の錯体も調製された。
以下に記載する以外は、次の手順を各重合に用いた。
(1)トルエンを溶媒として使用する場合、固体N,N−ジメチル−アニリニウムテトラ(ペンタフルオロフェニル)ボレート(DEATPFPB)の種々の量、又は
(2)ヘキサンを溶媒として使用する場合、シクロヘキサン中のジ(オクタデシル)メチルアンモニウムテトラキス(ペンタフルオロフェニル)ボレートの0.0326M溶液の種々の量。
後述の場合を除いて、実施例3〜7の方法を基本的に繰り返した。
実施例3〜7の方法を基本的に繰り返した。
実施例3〜7の方法を基本的に繰り返した。
実施例3〜7の方法を再度基本的に繰り返した。
Claims (22)
- ポリエン及びα−オレフィンマーの混合物を重合するのに有用な触媒組成物であって、前記組成物が次の一般式によって定義される錯体を含み、
式中、
Mは第3族金属原子を表し、
Lは中性ルイス塩基を表し、
zは0及び3を含む0〜3の整数であり、
mは1又は2であり、ただしmが2のときシリル基はインデニル配位子の1位及び3位にあり、
nは1又は2であり、
各R1は独立してH、ハロゲン原子、C1〜C20アルキル基、C5〜C8シクロアルキル基、アラルキル基、アルコキシ基、シロキシ基、ニトロ基、スルホネート基、又は−(CH2)yR3基であり、ここでyは0又は1であり、R3は置換若しくは非置換アリール基であり、
R2はX型モノアニオン性配位子であり、
任意に以下の
(1)zが0でないとき、L基及びR2基は、それぞれが結合している前記M原子と共に、結合して環状部分を提供することができる、並びに
(2)2つのR1基が結合して、置換又は非置換ヒドロカルビレン基を形成することができ、Si原子と一緒になって環状部分を形成することができる、のうちの1つ又は両方が当てはまり得る、触媒組成物。 - 前記錯体のzが0である、請求項1に記載の触媒組成物。
- 前記錯体のMがランタノイド金属原子である、請求項1に記載の触媒組成物。
- 前記錯体のmが1であり、前記シリル基が前記インデニル配位子の1位で結合している、請求項1に記載の触媒組成物。
- 前記錯体の少なくとも1つのR1が−(CH2)yR3である、請求項1に記載の触媒組成物。
- yが1である、請求項5に記載の触媒組成物。
- アルキル化剤及び非配位性アニオン又は非配位性アニオン前駆体のうちの少なくとも1つを含む触媒活性化剤を更に含む、請求項1に記載の触媒組成物。
- ポリマーを提供する方法であって、前記方法が1つ以上のエチレン性不飽和炭化水素に請求項1〜7のいずれか一項に記載の触媒組成物を接触させることと、前記ポリマーをそこから形成させることと、を含み、前記方法が末端官能基を前記ポリマーに提供するため任意に前記ポリマーを官能化剤と反応させることを更に含む、方法。
- 前記1つ以上のエチレン性不飽和炭化水素が少なくとも1つの共役ジエン化合物を含む、請求項8に記載の方法。
- 前記1つ以上のエチレン性不飽和炭化水素が少なくとも1つのα−オレフィンを更に含む、請求項9に記載の方法。
- 前記共役ジエンマーの少なくとも1/2が1,4−シス配置に組み込まれている、請求項10に記載の方法。
- 前記ポリマーが共役ジエンマーの少なくとも1つのブロックと、ランダムに分布した共役ジエン及びα−オレフィンマーの少なくとも1つのブロックと、を含む、請求項11に記載の方法。
- ポリエンマー及び40〜75モル%のエチレンマーを含むインターポリマーであって、複数の前記エチレンマーがランダムに分布している、インターポリマー。
- 少なくとも1つのブロックのポリエンマーを含み、前記ポリエンマーの25〜99モル%が任意にランダムに分布している、請求項13に記載のインターポリマー。
- 前記ポリエンマーがジエンマーを含み、以下、
その13C核磁気共鳴分光学法のプロットが32.1ppm及び32.2ppmの1つ以上にピークを含む、及び
そのプロトン核磁気共鳴分光法分のプロットが1.85〜2.02ppmの間にピークを含む、のうちの少なくとも1つが前記インターポリマーについて当てはまる、請求項14に記載のインターポリマー。 - 前記ポリエンマーの0モル%より大きく10モル%までがビニル−1,2配置に組み込まれている、請求項13に記載のインターポリマー。
- 組成物であって、
a)1つ以上のC5〜C10アルカンの少なくとも50重量%を含む、又は任意に1つ以上のC5〜C10アルカンからなる溶媒系と、
b)ポリエンマー及び少なくとも10モル%のエチレンマーを含むインターポリマーであって、複数の前記エチレンマーが前記インターポリマーに任意にランダムに分布している、インターポリマーと、を含む、組成物。 - 前記インターポリマーが少なくとも33モル%のエチレンマーを含む、請求項17に記載の組成物。
- 前記インターポリマーが少なくとも50モル%のエチレンマーを含む、請求項18に記載の組成物。
- 前記インターポリマーがランダムに分布しているエチレンマーを含み、前記インターポリマーがポリエンマーの少なくとも1つのブロックを更に含み、前記ポリエンマーが任意に少なくとも1つの種類のジエンマーを含む、請求項17に記載の組成物。
- 前記ポリエンマーの25〜99モル%がランダムに分布している、請求項20に記載の組成物。
- 前記ポリエンマーの0モル%より大きく10モル%までがビニル−1,2配置に組み込まれている、請求項17に記載の組成物。
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RU2723019C2 (ru) | 2020-06-08 |
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JP2017516911A (ja) | 2017-06-22 |
JP6673596B2 (ja) | 2020-03-25 |
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US20170114170A1 (en) | 2017-04-27 |
CN106660819B (zh) | 2019-06-28 |
BR112016027987B1 (pt) | 2022-04-19 |
CN110283280B (zh) | 2022-11-04 |
JP7187432B2 (ja) | 2022-12-12 |
US11124591B2 (en) | 2021-09-21 |
RU2016147087A3 (ja) | 2018-12-11 |
EP3148938A1 (en) | 2017-04-05 |
US10457765B2 (en) | 2019-10-29 |
EP3148938A4 (en) | 2018-05-30 |
US20200031974A1 (en) | 2020-01-30 |
RU2019115933A3 (ja) | 2019-08-12 |
CN110283280A (zh) | 2019-09-27 |
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