WO2006129773A1 - アミノシラン化合物、オレフィン類重合用触媒成分および触媒並びにこれを用いたオレフィン類重合体の製造方法 - Google Patents
アミノシラン化合物、オレフィン類重合用触媒成分および触媒並びにこれを用いたオレフィン類重合体の製造方法 Download PDFInfo
- Publication number
- WO2006129773A1 WO2006129773A1 PCT/JP2006/311038 JP2006311038W WO2006129773A1 WO 2006129773 A1 WO2006129773 A1 WO 2006129773A1 JP 2006311038 W JP2006311038 W JP 2006311038W WO 2006129773 A1 WO2006129773 A1 WO 2006129773A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- bis
- group
- polymerization
- methylamino
- silane
- Prior art date
Links
- 238000006116 polymerization reaction Methods 0.000 title claims abstract description 127
- 239000003054 catalyst Substances 0.000 title claims abstract description 73
- 150000001336 alkenes Chemical class 0.000 title claims abstract description 60
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 17
- 238000000034 method Methods 0.000 title abstract description 31
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 title abstract description 13
- 229920000098 polyolefin Polymers 0.000 title abstract description 7
- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical class [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 title abstract description 7
- -1 aminosilane compound Chemical class 0.000 claims abstract description 213
- 150000001875 compounds Chemical class 0.000 claims abstract description 55
- 239000011949 solid catalyst Substances 0.000 claims abstract description 47
- 239000011777 magnesium Substances 0.000 claims abstract description 30
- 229910052719 titanium Inorganic materials 0.000 claims abstract description 28
- 239000010936 titanium Substances 0.000 claims abstract description 27
- 229910052749 magnesium Inorganic materials 0.000 claims abstract description 17
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims abstract description 16
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims abstract description 16
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 7
- 150000002367 halogens Chemical class 0.000 claims abstract description 6
- 229910052782 aluminium Inorganic materials 0.000 claims abstract description 5
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 82
- 229920000642 polymer Polymers 0.000 claims description 42
- 125000000217 alkyl group Chemical group 0.000 claims description 41
- 239000002685 polymerization catalyst Substances 0.000 claims description 40
- RXVAWVPVNXHVFX-UHFFFAOYSA-N n-[dicyclopentyl(ethylamino)silyl]ethanamine Chemical compound C1CCCC1[Si](NCC)(NCC)C1CCCC1 RXVAWVPVNXHVFX-UHFFFAOYSA-N 0.000 claims description 28
- 125000004432 carbon atom Chemical group C* 0.000 claims description 27
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 21
- 125000003118 aryl group Chemical group 0.000 claims description 20
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 19
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 19
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
- 125000004122 cyclic group Chemical group 0.000 claims description 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- 150000002681 magnesium compounds Chemical class 0.000 claims description 10
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 7
- JTGAUXSVQKWNHO-UHFFFAOYSA-N ditert-butylsilicon Chemical compound CC(C)(C)[Si]C(C)(C)C JTGAUXSVQKWNHO-UHFFFAOYSA-N 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims description 6
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 6
- MZVVKQYKHJJXCB-UHFFFAOYSA-N n-[ethylamino-di(propan-2-yl)silyl]ethanamine Chemical compound CCN[Si](C(C)C)(C(C)C)NCC MZVVKQYKHJJXCB-UHFFFAOYSA-N 0.000 claims description 5
- 230000000379 polymerizing effect Effects 0.000 claims description 5
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims 1
- 125000006267 biphenyl group Chemical group 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 31
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract description 22
- 239000001257 hydrogen Substances 0.000 abstract description 21
- 230000003197 catalytic effect Effects 0.000 abstract description 10
- 229920000576 tactic polymer Polymers 0.000 abstract description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 189
- 239000000243 solution Substances 0.000 description 137
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 105
- 229910000077 silane Inorganic materials 0.000 description 101
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 98
- 239000007983 Tris buffer Substances 0.000 description 91
- 125000003282 alkyl amino group Chemical group 0.000 description 77
- 238000006243 chemical reaction Methods 0.000 description 64
- 230000015572 biosynthetic process Effects 0.000 description 56
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 54
- 229910052757 nitrogen Inorganic materials 0.000 description 46
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 42
- 239000007787 solid Substances 0.000 description 40
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 39
- 239000000047 product Substances 0.000 description 37
- 229910001873 dinitrogen Inorganic materials 0.000 description 35
- 238000002474 experimental method Methods 0.000 description 35
- 238000003756 stirring Methods 0.000 description 33
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 33
- 239000002904 solvent Substances 0.000 description 28
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 27
- 150000003839 salts Chemical class 0.000 description 26
- 239000002002 slurry Substances 0.000 description 26
- 238000000921 elemental analysis Methods 0.000 description 25
- 125000004888 n-propyl amino group Chemical group [H]N(*)C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 25
- 239000002253 acid Substances 0.000 description 22
- 238000003786 synthesis reaction Methods 0.000 description 22
- LXQCYGJKOIEWBN-UHFFFAOYSA-N pentylsilane Chemical compound CCCCC[SiH3] LXQCYGJKOIEWBN-UHFFFAOYSA-N 0.000 description 20
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 18
- 239000002245 particle Substances 0.000 description 18
- 150000002430 hydrocarbons Chemical class 0.000 description 17
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
- XNGIFLGASWRNHJ-UHFFFAOYSA-N o-dicarboxybenzene Natural products OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 16
- 235000001055 magnesium Nutrition 0.000 description 15
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 15
- 229910052799 carbon Inorganic materials 0.000 description 14
- 238000004821 distillation Methods 0.000 description 14
- 239000000203 mixture Substances 0.000 description 14
- 238000002360 preparation method Methods 0.000 description 14
- 150000001343 alkyl silanes Chemical class 0.000 description 13
- 239000007788 liquid Substances 0.000 description 13
- 238000009835 boiling Methods 0.000 description 12
- ZXPDYFSTVHQQOI-UHFFFAOYSA-N diethoxysilane Chemical compound CCO[SiH2]OCC ZXPDYFSTVHQQOI-UHFFFAOYSA-N 0.000 description 12
- 229920001296 polysiloxane Polymers 0.000 description 12
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 11
- 239000012298 atmosphere Substances 0.000 description 11
- 125000002619 bicyclic group Chemical group 0.000 description 11
- 125000004663 dialkyl amino group Chemical group 0.000 description 11
- 150000003377 silicon compounds Chemical class 0.000 description 11
- 239000012265 solid product Substances 0.000 description 11
- 239000000725 suspension Substances 0.000 description 11
- 239000011541 reaction mixture Substances 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- MGWAVDBGNNKXQV-UHFFFAOYSA-N diisobutyl phthalate Chemical compound CC(C)COC(=O)C1=CC=CC=C1C(=O)OCC(C)C MGWAVDBGNNKXQV-UHFFFAOYSA-N 0.000 description 9
- 238000009826 distribution Methods 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
- 235000019441 ethanol Nutrition 0.000 description 9
- 239000000155 melt Substances 0.000 description 9
- 229910052751 metal Inorganic materials 0.000 description 9
- 239000002184 metal Substances 0.000 description 9
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 9
- 238000005406 washing Methods 0.000 description 9
- 238000005119 centrifugation Methods 0.000 description 8
- 238000007334 copolymerization reaction Methods 0.000 description 8
- 239000011261 inert gas Substances 0.000 description 8
- 229910003002 lithium salt Inorganic materials 0.000 description 8
- 159000000002 lithium salts Chemical class 0.000 description 8
- UIUXUFNYAYAMOE-UHFFFAOYSA-N methylsilane Chemical compound [SiH3]C UIUXUFNYAYAMOE-UHFFFAOYSA-N 0.000 description 8
- 239000000843 powder Substances 0.000 description 8
- OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 description 7
- YWWFOSIVWXHIDF-UHFFFAOYSA-N n-[tris(methylamino)silyl]methanamine Chemical compound CN[Si](NC)(NC)NC YWWFOSIVWXHIDF-UHFFFAOYSA-N 0.000 description 7
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 7
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 6
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
- 238000005481 NMR spectroscopy Methods 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 6
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 6
- 150000004756 silanes Chemical class 0.000 description 6
- LFQCEHFDDXELDD-UHFFFAOYSA-N tetramethyl orthosilicate Chemical compound CO[Si](OC)(OC)OC LFQCEHFDDXELDD-UHFFFAOYSA-N 0.000 description 6
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 5
- 239000004215 Carbon black (E152) Substances 0.000 description 5
- 150000001408 amides Chemical class 0.000 description 5
- 125000006310 cycloalkyl amino group Chemical group 0.000 description 5
- MCPOBKGRILHVPP-UHFFFAOYSA-N dicyclopentylsilane Chemical compound C1CCCC1[SiH2]C1CCCC1 MCPOBKGRILHVPP-UHFFFAOYSA-N 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
- 229930195733 hydrocarbon Natural products 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 238000005259 measurement Methods 0.000 description 5
- 239000011259 mixed solution Substances 0.000 description 5
- 150000003141 primary amines Chemical class 0.000 description 5
- PSWKAZOCOHMXCW-UHFFFAOYSA-N tert-butyl-ethyl-dimethoxysilane Chemical compound CC[Si](OC)(OC)C(C)(C)C PSWKAZOCOHMXCW-UHFFFAOYSA-N 0.000 description 5
- ZWVDTRNPSDMWTB-UHFFFAOYSA-N 2-methylpropylsilane Chemical compound CC(C)C[SiH3] ZWVDTRNPSDMWTB-UHFFFAOYSA-N 0.000 description 4
- AZXKGUVDIORSED-UHFFFAOYSA-N 4-bromophthalic acid Chemical compound OC(=O)C1=CC=C(Br)C=C1C(O)=O AZXKGUVDIORSED-UHFFFAOYSA-N 0.000 description 4
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 4
- 239000005977 Ethylene Substances 0.000 description 4
- PXBCPOWAVFMNQD-UHFFFAOYSA-N N-silylethanamine Chemical compound CCN[SiH3] PXBCPOWAVFMNQD-UHFFFAOYSA-N 0.000 description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
- 238000012661 block copolymerization Methods 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 4
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 4
- 150000001354 dialkyl silanes Chemical class 0.000 description 4
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 4
- YQGOWXYZDLJBFL-UHFFFAOYSA-N dimethoxysilane Chemical compound CO[SiH2]OC YQGOWXYZDLJBFL-UHFFFAOYSA-N 0.000 description 4
- 229960001826 dimethylphthalate Drugs 0.000 description 4
- UBHZUDXTHNMNLD-UHFFFAOYSA-N dimethylsilane Chemical compound C[SiH2]C UBHZUDXTHNMNLD-UHFFFAOYSA-N 0.000 description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
- 239000000178 monomer Substances 0.000 description 4
- YYVGYULIMDRZMJ-UHFFFAOYSA-N propan-2-ylsilane Chemical compound CC(C)[SiH3] YYVGYULIMDRZMJ-UHFFFAOYSA-N 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 238000001308 synthesis method Methods 0.000 description 4
- KNSVRQSOPKYFJN-UHFFFAOYSA-N tert-butylsilicon Chemical compound CC(C)(C)[Si] KNSVRQSOPKYFJN-UHFFFAOYSA-N 0.000 description 4
- BTUUJXBKBIRHPP-UHFFFAOYSA-N 2-(3-methylbutoxycarbonyl)benzoic acid Chemical compound CC(C)CCOC(=O)C1=CC=CC=C1C(O)=O BTUUJXBKBIRHPP-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- AJIIPJIKASDPKD-UHFFFAOYSA-N C1CCCCC1[SiH2]C1CCCCC1 Chemical compound C1CCCCC1[SiH2]C1CCCCC1 AJIIPJIKASDPKD-UHFFFAOYSA-N 0.000 description 3
- DAEXGDSKPVNFGH-UHFFFAOYSA-N CO[Mg] Chemical compound CO[Mg] DAEXGDSKPVNFGH-UHFFFAOYSA-N 0.000 description 3
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- CFGPOQAHCQQVHW-UHFFFAOYSA-N N-silylpropan-1-amine Chemical compound CCCN[SiH3] CFGPOQAHCQQVHW-UHFFFAOYSA-N 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 150000003973 alkyl amines Chemical class 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- MQUBEBJFHBANKV-UHFFFAOYSA-N di(propan-2-yl)silicon Chemical compound CC(C)[Si]C(C)C MQUBEBJFHBANKV-UHFFFAOYSA-N 0.000 description 3
- VHPUZTHRFWIGAW-UHFFFAOYSA-N dimethoxy-di(propan-2-yl)silane Chemical compound CO[Si](OC)(C(C)C)C(C)C VHPUZTHRFWIGAW-UHFFFAOYSA-N 0.000 description 3
- KCWYOFZQRFCIIE-UHFFFAOYSA-N ethylsilane Chemical compound CC[SiH3] KCWYOFZQRFCIIE-UHFFFAOYSA-N 0.000 description 3
- 239000012456 homogeneous solution Substances 0.000 description 3
- 238000002329 infrared spectrum Methods 0.000 description 3
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- FPGPRAKRYDSZAW-UHFFFAOYSA-N monopentyl phthalate Chemical compound CCCCCOC(=O)C1=CC=CC=C1C(O)=O FPGPRAKRYDSZAW-UHFFFAOYSA-N 0.000 description 3
- SNEYFYICQMWMPF-UHFFFAOYSA-N n-[dicyclohexyl(methylamino)silyl]methanamine Chemical compound C1CCCCC1[Si](NC)(NC)C1CCCCC1 SNEYFYICQMWMPF-UHFFFAOYSA-N 0.000 description 3
- OMEWDINONHKQRQ-UHFFFAOYSA-N n-[dicyclopentyl(propylamino)silyl]propan-1-amine Chemical compound C1CCCC1[Si](NCCC)(NCCC)C1CCCC1 OMEWDINONHKQRQ-UHFFFAOYSA-N 0.000 description 3
- XJEJSMCUIKZVAW-UHFFFAOYSA-N n-silylmethanamine Chemical compound CN[SiH3] XJEJSMCUIKZVAW-UHFFFAOYSA-N 0.000 description 3
- KZUZCAUCLFNXCU-UHFFFAOYSA-N n-tert-butyl-2-methyl-n-trimethoxysilylpropan-2-amine Chemical compound CO[Si](OC)(OC)N(C(C)(C)C)C(C)(C)C KZUZCAUCLFNXCU-UHFFFAOYSA-N 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- YLYBTZIQSIBWLI-UHFFFAOYSA-N octyl acetate Chemical compound CCCCCCCCOC(C)=O YLYBTZIQSIBWLI-UHFFFAOYSA-N 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- JANBFCARANRIKJ-UHFFFAOYSA-N phthalic acid diisopentyl ester Natural products CC(C)CCOC(=O)C1=CC=CC=C1C(=O)OCCC(C)C JANBFCARANRIKJ-UHFFFAOYSA-N 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 150000003335 secondary amines Chemical class 0.000 description 3
- 239000006104 solid solution Substances 0.000 description 3
- REBPHVJMYRKOET-UHFFFAOYSA-N tert-butyl(ethyl)silane Chemical compound CC[SiH2]C(C)(C)C REBPHVJMYRKOET-UHFFFAOYSA-N 0.000 description 3
- UTADZBVVSYSYTG-UHFFFAOYSA-N tert-butyl(methyl)silane Chemical compound C[SiH2]C(C)(C)C UTADZBVVSYSYTG-UHFFFAOYSA-N 0.000 description 3
- 150000003609 titanium compounds Chemical class 0.000 description 3
- QQQSFSZALRVCSZ-UHFFFAOYSA-N triethoxysilane Chemical compound CCO[SiH](OCC)OCC QQQSFSZALRVCSZ-UHFFFAOYSA-N 0.000 description 3
- VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 description 3
- 238000005292 vacuum distillation Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- VUGMARFZKDASCX-UHFFFAOYSA-N 2-methyl-N-silylpropan-2-amine Chemical compound CC(C)(C)N[SiH3] VUGMARFZKDASCX-UHFFFAOYSA-N 0.000 description 2
- ZEYHEAKUIGZSGI-UHFFFAOYSA-N 4-methoxybenzoic acid Chemical compound COC1=CC=C(C(O)=O)C=C1 ZEYHEAKUIGZSGI-UHFFFAOYSA-N 0.000 description 2
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- GVRWMSWKQJZYMB-UHFFFAOYSA-N C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C34.C=CC Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C34.C=CC GVRWMSWKQJZYMB-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- 241000270722 Crocodylidae Species 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- XMSXQFUHVRWGNA-UHFFFAOYSA-N Decamethylcyclopentasiloxane Chemical compound C[Si]1(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O1 XMSXQFUHVRWGNA-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- NIQCNGHVCWTJSM-UHFFFAOYSA-N Dimethyl phthalate Chemical compound COC(=O)C1=CC=CC=C1C(=O)OC NIQCNGHVCWTJSM-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- NIPNSKYNPDTRPC-UHFFFAOYSA-N N-[2-oxo-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 NIPNSKYNPDTRPC-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- BTKXSYWWRGMQHR-UHFFFAOYSA-N [amino(diethoxy)silyl]oxyethane Chemical compound CCO[Si](N)(OCC)OCC BTKXSYWWRGMQHR-UHFFFAOYSA-N 0.000 description 2
- VTAFVPRBZJEEDR-UHFFFAOYSA-N acetylsilicon Chemical compound CC([Si])=O VTAFVPRBZJEEDR-UHFFFAOYSA-N 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 150000004996 alkyl benzenes Chemical class 0.000 description 2
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 230000001186 cumulative effect Effects 0.000 description 2
- 150000004292 cyclic ethers Chemical class 0.000 description 2
- WUOREHWHBFMWDG-UHFFFAOYSA-N cyclohexyl(cyclopentyl)silane Chemical compound C1CCCC1[SiH2]C1CCCCC1 WUOREHWHBFMWDG-UHFFFAOYSA-N 0.000 description 2
- TZKUEMHGRFBQIX-UHFFFAOYSA-N cyclohexylmethylsilane Chemical compound [SiH3]CC1CCCCC1 TZKUEMHGRFBQIX-UHFFFAOYSA-N 0.000 description 2
- UMQOSQJMIIITHA-UHFFFAOYSA-N cyclohexylsilane Chemical compound [SiH3]C1CCCCC1 UMQOSQJMIIITHA-UHFFFAOYSA-N 0.000 description 2
- LNNWVNGFPYWNQE-GMIGKAJZSA-N desomorphine Chemical compound C1C2=CC=C(O)C3=C2[C@]24CCN(C)[C@H]1[C@@H]2CCC[C@@H]4O3 LNNWVNGFPYWNQE-GMIGKAJZSA-N 0.000 description 2
- 150000001983 dialkylethers Chemical class 0.000 description 2
- JWCYDYZLEAQGJJ-UHFFFAOYSA-N dicyclopentyl(dimethoxy)silane Chemical compound C1CCCC1[Si](OC)(OC)C1CCCC1 JWCYDYZLEAQGJJ-UHFFFAOYSA-N 0.000 description 2
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- FLKPEMZONWLCSK-UHFFFAOYSA-N diethyl phthalate Chemical compound CCOC(=O)C1=CC=CC=C1C(=O)OCC FLKPEMZONWLCSK-UHFFFAOYSA-N 0.000 description 2
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 2
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000004205 dimethyl polysiloxane Substances 0.000 description 2
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 2
- MQHNKCZKNAJROC-UHFFFAOYSA-N dipropyl phthalate Chemical compound CCCOC(=O)C1=CC=CC=C1C(=O)OCCC MQHNKCZKNAJROC-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- MTZQAGJQAFMTAQ-UHFFFAOYSA-N ethyl benzoate Chemical compound CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 description 2
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 125000001245 hexylamino group Chemical group [H]N([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 2
- QGGUMTNPIYCTSF-UHFFFAOYSA-N hexylsilane Chemical compound CCCCCC[SiH3] QGGUMTNPIYCTSF-UHFFFAOYSA-N 0.000 description 2
- 238000001746 injection moulding Methods 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 239000012948 isocyanate Substances 0.000 description 2
- 150000002513 isocyanates Chemical class 0.000 description 2
- 150000002680 magnesium Chemical class 0.000 description 2
- QUXHCILOWRXCEO-UHFFFAOYSA-M magnesium;butane;chloride Chemical compound [Mg+2].[Cl-].CCC[CH2-] QUXHCILOWRXCEO-UHFFFAOYSA-M 0.000 description 2
- CRGZYKWWYNQGEC-UHFFFAOYSA-N magnesium;methanolate Chemical compound [Mg+2].[O-]C.[O-]C CRGZYKWWYNQGEC-UHFFFAOYSA-N 0.000 description 2
- TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 2
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 2
- MLOPFSAVPPFORP-UHFFFAOYSA-N n-[bis(dipropylamino)-(methylamino)silyl]-n-propylpropan-1-amine Chemical compound CCCN(CCC)[Si](NC)(N(CCC)CCC)N(CCC)CCC MLOPFSAVPPFORP-UHFFFAOYSA-N 0.000 description 2
- RDRGPASZKXBRKM-UHFFFAOYSA-N n-[bis(ethylamino)silyl]ethanamine Chemical compound CCN[SiH](NCC)NCC RDRGPASZKXBRKM-UHFFFAOYSA-N 0.000 description 2
- ZDRLPBVAYORIIQ-UHFFFAOYSA-N n-[cyclohexyl-bis(methylamino)silyl]methanamine Chemical compound CN[Si](NC)(NC)C1CCCCC1 ZDRLPBVAYORIIQ-UHFFFAOYSA-N 0.000 description 2
- HECCPDQWXXAFAP-UHFFFAOYSA-N n-[dicyclopentyl(methylamino)silyl]methanamine Chemical group C1CCCC1[Si](NC)(NC)C1CCCC1 HECCPDQWXXAFAP-UHFFFAOYSA-N 0.000 description 2
- HUDSDLIIKRMTIU-UHFFFAOYSA-N n-[ethyl-bis(methylamino)silyl]methanamine Chemical compound CC[Si](NC)(NC)NC HUDSDLIIKRMTIU-UHFFFAOYSA-N 0.000 description 2
- OSCCDXHPMYNADD-UHFFFAOYSA-N n-[methyl-bis(methylamino)silyl]methanamine Chemical compound CN[Si](C)(NC)NC OSCCDXHPMYNADD-UHFFFAOYSA-N 0.000 description 2
- XTXDZHNKTHWKAJ-UHFFFAOYSA-N n-[tert-butyl-ethyl-(methylamino)silyl]methanamine Chemical compound CC[Si](NC)(NC)C(C)(C)C XTXDZHNKTHWKAJ-UHFFFAOYSA-N 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- FTFOGZDTAFCTNN-UHFFFAOYSA-N n-butyl-n-[(dibutylamino)-bis(propylamino)silyl]butan-1-amine Chemical compound CCCCN(CCCC)[Si](NCCC)(NCCC)N(CCCC)CCCC FTFOGZDTAFCTNN-UHFFFAOYSA-N 0.000 description 2
- BQBJQKKUDVHKJZ-UHFFFAOYSA-N n-cyclohexyl-n-[tris(methylamino)silyl]cyclohexanamine Chemical compound C1CCCCC1N([Si](NC)(NC)NC)C1CCCCC1 BQBJQKKUDVHKJZ-UHFFFAOYSA-N 0.000 description 2
- VUTWNWNKVIKKAT-UHFFFAOYSA-N n-propan-2-yl-n-[tris(methylamino)silyl]propan-2-amine Chemical compound CN[Si](NC)(NC)N(C(C)C)C(C)C VUTWNWNKVIKKAT-UHFFFAOYSA-N 0.000 description 2
- LVPQHXFABFESGK-UHFFFAOYSA-N n-propan-2-yl-n-trimethoxysilylpropan-2-amine Chemical compound CO[Si](OC)(OC)N(C(C)C)C(C)C LVPQHXFABFESGK-UHFFFAOYSA-N 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 150000003961 organosilicon compounds Chemical class 0.000 description 2
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 2
- 125000004894 pentylamino group Chemical group C(CCCC)N* 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- 239000006187 pill Substances 0.000 description 2
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 229940090181 propyl acetate Drugs 0.000 description 2
- 125000006308 propyl amino group Chemical group 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- UIDUKLCLJMXFEO-UHFFFAOYSA-N propylsilane Chemical compound CCC[SiH3] UIDUKLCLJMXFEO-UHFFFAOYSA-N 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- NETBVGNWMHLXRP-UHFFFAOYSA-N tert-butyl-dimethoxy-methylsilane Chemical compound CO[Si](C)(OC)C(C)(C)C NETBVGNWMHLXRP-UHFFFAOYSA-N 0.000 description 2
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 2
- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 0.000 description 2
- ZQTYRTSKQFQYPQ-UHFFFAOYSA-N trisiloxane Chemical compound [SiH3]O[SiH2]O[SiH3] ZQTYRTSKQFQYPQ-UHFFFAOYSA-N 0.000 description 2
- DZGWFCGJZKJUFP-UHFFFAOYSA-N tyramine Chemical compound NCCC1=CC=C(O)C=C1 DZGWFCGJZKJUFP-UHFFFAOYSA-N 0.000 description 2
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 2
- UKRDPEFKFJNXQM-UHFFFAOYSA-N vinylsilane Chemical compound [SiH3]C=C UKRDPEFKFJNXQM-UHFFFAOYSA-N 0.000 description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- XAAPKTZIIJQVIB-UHFFFAOYSA-N 1,2,3,4,4a,5,6,7,8,8a-decahydronaphthalen-1-ylsilane Chemical compound C1(CCCC2CCCCC12)[SiH3] XAAPKTZIIJQVIB-UHFFFAOYSA-N 0.000 description 1
- UUAMLBIYJDPGFU-UHFFFAOYSA-N 1,3-dimethoxypropane Chemical compound COCCCOC UUAMLBIYJDPGFU-UHFFFAOYSA-N 0.000 description 1
- KZEVSDGEBAJOTK-UHFFFAOYSA-N 1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-2-[5-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]-1,3,4-oxadiazol-2-yl]ethanone Chemical compound N1N=NC=2CN(CCC=21)C(CC=1OC(=NN=1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)=O KZEVSDGEBAJOTK-UHFFFAOYSA-N 0.000 description 1
- YIWGJFPJRAEKMK-UHFFFAOYSA-N 1-(2H-benzotriazol-5-yl)-3-methyl-8-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carbonyl]-1,3,8-triazaspiro[4.5]decane-2,4-dione Chemical compound CN1C(=O)N(c2ccc3n[nH]nc3c2)C2(CCN(CC2)C(=O)c2cnc(NCc3cccc(OC(F)(F)F)c3)nc2)C1=O YIWGJFPJRAEKMK-UHFFFAOYSA-N 0.000 description 1
- FJLUATLTXUNBOT-UHFFFAOYSA-N 1-Hexadecylamine Chemical compound CCCCCCCCCCCCCCCCN FJLUATLTXUNBOT-UHFFFAOYSA-N 0.000 description 1
- HMUNWXXNJPVALC-UHFFFAOYSA-N 1-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)C(CN1CC2=C(CC1)NN=N2)=O HMUNWXXNJPVALC-UHFFFAOYSA-N 0.000 description 1
- HNAGHMKIPMKKBB-UHFFFAOYSA-N 1-benzylpyrrolidine-3-carboxamide Chemical compound C1C(C(=O)N)CCN1CC1=CC=CC=C1 HNAGHMKIPMKKBB-UHFFFAOYSA-N 0.000 description 1
- HWUKBLRCAWQFOL-UHFFFAOYSA-N 1-bromocyclohexa-3,5-diene-1,2-dicarboxylic acid Chemical compound OC(=O)C1C=CC=CC1(Br)C(O)=O HWUKBLRCAWQFOL-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- VFWCMGCRMGJXDK-UHFFFAOYSA-N 1-chlorobutane Chemical compound CCCCCl VFWCMGCRMGJXDK-UHFFFAOYSA-N 0.000 description 1
- GFLXBRUGMACJLQ-UHFFFAOYSA-N 1-isocyanatohexadecane Chemical compound CCCCCCCCCCCCCCCCN=C=O GFLXBRUGMACJLQ-UHFFFAOYSA-N 0.000 description 1
- HRJOMMSRROBCMQ-UHFFFAOYSA-N 1-o-methyl 2-o-(2-methylpropyl) benzene-1,2-dicarboxylate Chemical compound COC(=O)C1=CC=CC=C1C(=O)OCC(C)C HRJOMMSRROBCMQ-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- JODXKZAUFHEYGO-UHFFFAOYSA-N 2,3-dihydroxybutanedioyl dichloride Chemical compound ClC(=O)C(O)C(O)C(Cl)=O JODXKZAUFHEYGO-UHFFFAOYSA-N 0.000 description 1
- WZJUBBHODHNQPW-UHFFFAOYSA-N 2,4,6,8-tetramethyl-1,3,5,7,2$l^{3},4$l^{3},6$l^{3},8$l^{3}-tetraoxatetrasilocane Chemical compound C[Si]1O[Si](C)O[Si](C)O[Si](C)O1 WZJUBBHODHNQPW-UHFFFAOYSA-N 0.000 description 1
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 1
- LDXJRKWFNNFDSA-UHFFFAOYSA-N 2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]ethanone Chemical compound C1CN(CC2=NNN=C21)CC(=O)N3CCN(CC3)C4=CN=C(N=C4)NCC5=CC(=CC=C5)OC(F)(F)F LDXJRKWFNNFDSA-UHFFFAOYSA-N 0.000 description 1
- BLGXDBYELBCOFE-UHFFFAOYSA-N 2-(4-chlorophenoxy)carbonylbenzoic acid Chemical compound OC(=O)C1=CC=CC=C1C(=O)OC1=CC=C(Cl)C=C1 BLGXDBYELBCOFE-UHFFFAOYSA-N 0.000 description 1
- SXAMGRAIZSSWIH-UHFFFAOYSA-N 2-[3-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-1,2,4-oxadiazol-5-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1=NOC(=N1)CC(=O)N1CC2=C(CC1)NN=N2 SXAMGRAIZSSWIH-UHFFFAOYSA-N 0.000 description 1
- JQMFQLVAJGZSQS-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-N-(2-oxo-3H-1,3-benzoxazol-6-yl)acetamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)CC(=O)NC1=CC2=C(NC(O2)=O)C=C1 JQMFQLVAJGZSQS-UHFFFAOYSA-N 0.000 description 1
- IHCCLXNEEPMSIO-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperidin-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1CCN(CC1)CC(=O)N1CC2=C(CC1)NN=N2 IHCCLXNEEPMSIO-UHFFFAOYSA-N 0.000 description 1
- YJLUBHOZZTYQIP-UHFFFAOYSA-N 2-[5-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-1,3,4-oxadiazol-2-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1=NN=C(O1)CC(=O)N1CC2=C(CC1)NN=N2 YJLUBHOZZTYQIP-UHFFFAOYSA-N 0.000 description 1
- APLNAFMUEHKRLM-UHFFFAOYSA-N 2-[5-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-1,3,4-oxadiazol-2-yl]-1-(3,4,6,7-tetrahydroimidazo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1=NN=C(O1)CC(=O)N1CC2=C(CC1)N=CN2 APLNAFMUEHKRLM-UHFFFAOYSA-N 0.000 description 1
- APWRLAZEMYLHKZ-UHFFFAOYSA-N 2-amino-5,6-dimethyl-1h-pyrimidin-4-one Chemical class CC=1NC(N)=NC(=O)C=1C APWRLAZEMYLHKZ-UHFFFAOYSA-N 0.000 description 1
- VBZOUUJVGADJBK-UHFFFAOYSA-N 2-bromopropanedioic acid Chemical compound OC(=O)C(Br)C(O)=O VBZOUUJVGADJBK-UHFFFAOYSA-N 0.000 description 1
- VFYOBJVYPKBHAK-UHFFFAOYSA-N 2-methyl-n-(2-methylpropyl)-n-[tris(ethylamino)silyl]propan-1-amine Chemical compound CCN[Si](NCC)(NCC)N(CC(C)C)CC(C)C VFYOBJVYPKBHAK-UHFFFAOYSA-N 0.000 description 1
- RMHKUGQHNHEMRB-UHFFFAOYSA-N 2-methyl-n-[methyl-bis(methylamino)silyl]propan-1-amine Chemical compound CN[Si](C)(NC)NCC(C)C RMHKUGQHNHEMRB-UHFFFAOYSA-N 0.000 description 1
- OMMIAOPXHPUWSP-UHFFFAOYSA-N 2-methyl-n-[tris(propylamino)silyl]propan-2-amine Chemical compound CCCN[Si](NCCC)(NCCC)NC(C)(C)C OMMIAOPXHPUWSP-UHFFFAOYSA-N 0.000 description 1
- QIVBSAJFJWWGOS-UHFFFAOYSA-N 2-methyl-n-propyl-n-[tris(methylamino)silyl]propan-2-amine Chemical compound CCCN(C(C)(C)C)[Si](NC)(NC)NC QIVBSAJFJWWGOS-UHFFFAOYSA-N 0.000 description 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- ALKCLFLTXBBMMP-UHFFFAOYSA-N 3,7-dimethylocta-1,6-dien-3-yl hexanoate Chemical class CCCCCC(=O)OC(C)(C=C)CCC=C(C)C ALKCLFLTXBBMMP-UHFFFAOYSA-N 0.000 description 1
- YLZOPXRUQYQQID-UHFFFAOYSA-N 3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]propan-1-one Chemical compound N1N=NC=2CN(CCC=21)CCC(=O)N1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F YLZOPXRUQYQQID-UHFFFAOYSA-N 0.000 description 1
- SSUNPTAZLCAIDO-UHFFFAOYSA-N 3-[[amino(diethoxy)silyl]oxymethyl]-2,4-dimethylpentane Chemical compound C(C)(C)C(CO[Si](OCC)(OCC)N)C(C)C SSUNPTAZLCAIDO-UHFFFAOYSA-N 0.000 description 1
- OIGFNQRFPUUACU-UHFFFAOYSA-N 3-bromophthalic acid Chemical compound OC(=O)C1=CC=CC(Br)=C1C(O)=O OIGFNQRFPUUACU-UHFFFAOYSA-N 0.000 description 1
- KNIRLWRQSSLZCZ-UHFFFAOYSA-N 3-ethyloct-3-ene Chemical compound CCCCC=C(CC)CC KNIRLWRQSSLZCZ-UHFFFAOYSA-N 0.000 description 1
- GAIPRQZXSYSCRD-UHFFFAOYSA-N 4,5-dichloro-2-benzofuran-1,3-dione Chemical compound ClC1=CC=C2C(=O)OC(=O)C2=C1Cl GAIPRQZXSYSCRD-UHFFFAOYSA-N 0.000 description 1
- FDOQKGWUMUEJLX-UHFFFAOYSA-N 4,5-dichlorophthalic acid Chemical compound OC(=O)C1=CC(Cl)=C(Cl)C=C1C(O)=O FDOQKGWUMUEJLX-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
- DVIPPHSQIBKWSA-UHFFFAOYSA-N 4-chlorophthalic acid Chemical compound OC(=O)C1=CC=C(Cl)C=C1C(O)=O DVIPPHSQIBKWSA-UHFFFAOYSA-N 0.000 description 1
- CONKBQPVFMXDOV-QHCPKHFHSA-N 6-[(5S)-5-[[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]methyl]-2-oxo-1,3-oxazolidin-3-yl]-3H-1,3-benzoxazol-2-one Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)C[C@H]1CN(C(O1)=O)C1=CC2=C(NC(O2)=O)C=C1 CONKBQPVFMXDOV-QHCPKHFHSA-N 0.000 description 1
- WTFUTSCZYYCBAY-SXBRIOAWSA-N 6-[(E)-C-[[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]methyl]-N-hydroxycarbonimidoyl]-3H-1,3-benzoxazol-2-one Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)C/C(=N/O)/C1=CC2=C(NC(O2)=O)C=C1 WTFUTSCZYYCBAY-SXBRIOAWSA-N 0.000 description 1
- DFGKGUXTPFWHIX-UHFFFAOYSA-N 6-[2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]acetyl]-3H-1,3-benzoxazol-2-one Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)CC(=O)C1=CC2=C(NC(O2)=O)C=C1 DFGKGUXTPFWHIX-UHFFFAOYSA-N 0.000 description 1
- DEXFNLNNUZKHNO-UHFFFAOYSA-N 6-[3-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperidin-1-yl]-3-oxopropyl]-3H-1,3-benzoxazol-2-one Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1CCN(CC1)C(CCC1=CC2=C(NC(O2)=O)C=C1)=O DEXFNLNNUZKHNO-UHFFFAOYSA-N 0.000 description 1
- LLQHSBBZNDXTIV-UHFFFAOYSA-N 6-[5-[[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]methyl]-4,5-dihydro-1,2-oxazol-3-yl]-3H-1,3-benzoxazol-2-one Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)CC1CC(=NO1)C1=CC2=C(NC(O2)=O)C=C1 LLQHSBBZNDXTIV-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- GJCOSYZMQJWQCA-UHFFFAOYSA-N 9H-xanthene Chemical compound C1=CC=C2CC3=CC=CC=C3OC2=C1 GJCOSYZMQJWQCA-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- RKTLUMGUHVXROJ-UHFFFAOYSA-N C(C(C)(C)C)N[SiH3] Chemical compound C(C(C)(C)C)N[SiH3] RKTLUMGUHVXROJ-UHFFFAOYSA-N 0.000 description 1
- FFKLLXNOWVYKTJ-UHFFFAOYSA-N C(C)(C)N[SiH](CC(C)(C)C)C Chemical compound C(C)(C)N[SiH](CC(C)(C)C)C FFKLLXNOWVYKTJ-UHFFFAOYSA-N 0.000 description 1
- NHKMVVDYYXJUMW-UHFFFAOYSA-N C(C=1C(C(=O)OCCC(C)C)=CC=CC1)(=O)OCCC(C)C.C(C=1C(C(=O)O)=CC=CC1)(=O)O Chemical compound C(C=1C(C(=O)OCCC(C)C)=CC=CC1)(=O)OCCC(C)C.C(C=1C(C(=O)O)=CC=CC1)(=O)O NHKMVVDYYXJUMW-UHFFFAOYSA-N 0.000 description 1
- DVEYKVBKFNEEAE-UHFFFAOYSA-N CCCCOCCO[Mg] Chemical compound CCCCOCCO[Mg] DVEYKVBKFNEEAE-UHFFFAOYSA-N 0.000 description 1
- CRXSXWJRCZACOR-UHFFFAOYSA-N CCCN(CCC)[SiH2]N(CCC)CCC Chemical compound CCCN(CCC)[SiH2]N(CCC)CCC CRXSXWJRCZACOR-UHFFFAOYSA-N 0.000 description 1
- XIOSCRANHXMIII-UHFFFAOYSA-N CCC[SiH2]CCC Chemical compound CCC[SiH2]CCC XIOSCRANHXMIII-UHFFFAOYSA-N 0.000 description 1
- KNSKYZYNIRUQGR-UHFFFAOYSA-N CCN[SiH2]N(C)C Chemical compound CCN[SiH2]N(C)C KNSKYZYNIRUQGR-UHFFFAOYSA-N 0.000 description 1
- RHCFPFCOZGFTBO-UHFFFAOYSA-N CCN[Si] Chemical compound CCN[Si] RHCFPFCOZGFTBO-UHFFFAOYSA-N 0.000 description 1
- NTWOIGOPFDMZAE-UHFFFAOYSA-M CCO[Ti](Cl)(OCC)OCC Chemical compound CCO[Ti](Cl)(OCC)OCC NTWOIGOPFDMZAE-UHFFFAOYSA-M 0.000 description 1
- OBLQVTVXAHAZQM-UHFFFAOYSA-N CN(C)[Si](C1CCCC1)(C1CCCC1)N(C)C Chemical group CN(C)[Si](C1CCCC1)(C1CCCC1)N(C)C OBLQVTVXAHAZQM-UHFFFAOYSA-N 0.000 description 1
- MQMAVLOMMSLIKH-UHFFFAOYSA-N CN[SiH2]NC(C)CC Chemical compound CN[SiH2]NC(C)CC MQMAVLOMMSLIKH-UHFFFAOYSA-N 0.000 description 1
- GQQQOAXBLTWZMW-UHFFFAOYSA-N CN[SiH](C)NC Chemical compound CN[SiH](C)NC GQQQOAXBLTWZMW-UHFFFAOYSA-N 0.000 description 1
- SPEZDPAYHZREFR-UHFFFAOYSA-N CN[Si](CCCCCC)(NC)NC Chemical compound CN[Si](CCCCCC)(NC)NC SPEZDPAYHZREFR-UHFFFAOYSA-N 0.000 description 1
- WBNMKUZYQDORBN-UHFFFAOYSA-N C[SiH2]NC(C)(C)C Chemical compound C[SiH2]NC(C)(C)C WBNMKUZYQDORBN-UHFFFAOYSA-N 0.000 description 1
- FZEDHKJXDVFMGT-UHFFFAOYSA-N Cl(=O)O.C(C=1C(C(=O)O)=CC=CC1)(=O)O Chemical compound Cl(=O)O.C(C=1C(C(=O)O)=CC=CC1)(=O)O FZEDHKJXDVFMGT-UHFFFAOYSA-N 0.000 description 1
- 229940126062 Compound A Drugs 0.000 description 1
- KCXZNSGUUQJJTR-UHFFFAOYSA-N Di-n-hexyl phthalate Chemical group CCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCC KCXZNSGUUQJJTR-UHFFFAOYSA-N 0.000 description 1
- XTJFFFGAUHQWII-UHFFFAOYSA-N Dibutyl adipate Chemical class CCCCOC(=O)CCCCC(=O)OCCCC XTJFFFGAUHQWII-UHFFFAOYSA-N 0.000 description 1
- ZVFDTKUVRCTHQE-UHFFFAOYSA-N Diisodecyl phthalate Chemical compound CC(C)CCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC(C)C ZVFDTKUVRCTHQE-UHFFFAOYSA-N 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Chemical group 0.000 description 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 1
- 239000007818 Grignard reagent Substances 0.000 description 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 1
- 241000286819 Malo Species 0.000 description 1
- SLOMTDIORDREGP-UHFFFAOYSA-N N-(ethylaminosilyl)ethanamine Chemical compound CCN[SiH2]NCC SLOMTDIORDREGP-UHFFFAOYSA-N 0.000 description 1
- MKYBYDHXWVHEJW-UHFFFAOYSA-N N-[1-oxo-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propan-2-yl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(C(C)NC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 MKYBYDHXWVHEJW-UHFFFAOYSA-N 0.000 description 1
- NEAPKZHDYMQZCB-UHFFFAOYSA-N N-[2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]ethyl]-2-oxo-3H-1,3-benzoxazole-6-carboxamide Chemical compound C1CN(CCN1CCNC(=O)C2=CC3=C(C=C2)NC(=O)O3)C4=CN=C(N=C4)NC5CC6=CC=CC=C6C5 NEAPKZHDYMQZCB-UHFFFAOYSA-N 0.000 description 1
- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 1
- NNDPHUJPRUBQPI-UHFFFAOYSA-N N-[cyclohexylmethyl(methylamino)silyl]methanamine Chemical compound CN[SiH](CC1CCCCC1)NC NNDPHUJPRUBQPI-UHFFFAOYSA-N 0.000 description 1
- SFLARCZJKUXPCE-UHFFFAOYSA-N N-butan-2-yl-N-silylbutan-2-amine Chemical compound CCC(C)N([SiH3])C(C)CC SFLARCZJKUXPCE-UHFFFAOYSA-N 0.000 description 1
- BFZQHCKWTZGAST-UHFFFAOYSA-N N-butyl-N-[(dibutylamino)-bis(diethylamino)silyl]butan-1-amine Chemical compound C(C)N(CC)[Si](N(CCCC)CCCC)(N(CCCC)CCCC)N(CC)CC BFZQHCKWTZGAST-UHFFFAOYSA-N 0.000 description 1
- KNNJUXSJVYVZIQ-UHFFFAOYSA-N N-dicyclopentylsilylethanamine Chemical compound C1(CCCC1)[SiH](NCC)C1CCCC1 KNNJUXSJVYVZIQ-UHFFFAOYSA-N 0.000 description 1
- XFYAHDIKXXRQFP-UHFFFAOYSA-N N-ethyl-N-[ethyl-bis(methylamino)silyl]butan-2-amine Chemical compound CCC(C)N(CC)[Si](CC)(NC)NC XFYAHDIKXXRQFP-UHFFFAOYSA-N 0.000 description 1
- VOMWUYKLAZENRC-UHFFFAOYSA-N N-ethyl-N-[methyl-bis(methylamino)silyl]cyclopentanamine Chemical compound CN[Si](C)(NC)N(CC)C1CCCC1 VOMWUYKLAZENRC-UHFFFAOYSA-N 0.000 description 1
- TYJPDWUPMHZTDX-UHFFFAOYSA-N N-ethyl-N-silylbutan-2-amine Chemical compound CCC(C)N([SiH3])CC TYJPDWUPMHZTDX-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 241000233855 Orchidaceae Species 0.000 description 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
- 241000555745 Sciuridae Species 0.000 description 1
- BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical compound CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 description 1
- FHKPLLOSJHHKNU-INIZCTEOSA-N [(3S)-3-[8-(1-ethyl-5-methylpyrazol-4-yl)-9-methylpurin-6-yl]oxypyrrolidin-1-yl]-(oxan-4-yl)methanone Chemical compound C(C)N1N=CC(=C1C)C=1N(C2=NC=NC(=C2N=1)O[C@@H]1CN(CC1)C(=O)C1CCOCC1)C FHKPLLOSJHHKNU-INIZCTEOSA-N 0.000 description 1
- JAWMENYCRQKKJY-UHFFFAOYSA-N [3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-ylmethyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-en-8-yl]-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]methanone Chemical compound N1N=NC=2CN(CCC=21)CC1=NOC2(C1)CCN(CC2)C(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F JAWMENYCRQKKJY-UHFFFAOYSA-N 0.000 description 1
- QSMLJCIHMPUAQG-UHFFFAOYSA-L [Cl-].[Cl-].CCCO[Ti+2]OCCC Chemical compound [Cl-].[Cl-].CCCO[Ti+2]OCCC QSMLJCIHMPUAQG-UHFFFAOYSA-L 0.000 description 1
- GKQZBJMXIUKBGB-UHFFFAOYSA-K [Cl-].[Cl-].[Cl-].CCCO[Ti+3] Chemical compound [Cl-].[Cl-].[Cl-].CCCO[Ti+3] GKQZBJMXIUKBGB-UHFFFAOYSA-K 0.000 description 1
- CARRLWRDCUHXCK-UHFFFAOYSA-N [SiH3]NC1CCCCC1 Chemical class [SiH3]NC1CCCCC1 CARRLWRDCUHXCK-UHFFFAOYSA-N 0.000 description 1
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
- UGAPHEBNTGUMBB-UHFFFAOYSA-N acetic acid;ethyl acetate Chemical compound CC(O)=O.CCOC(C)=O UGAPHEBNTGUMBB-UHFFFAOYSA-N 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- VRAIHTAYLFXSJJ-UHFFFAOYSA-N alumane Chemical compound [AlH3].[AlH3] VRAIHTAYLFXSJJ-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
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- UWAXDPWQPGZNIO-UHFFFAOYSA-N benzylsilane Chemical compound [SiH3]CC1=CC=CC=C1 UWAXDPWQPGZNIO-UHFFFAOYSA-N 0.000 description 1
- QTNGGWXXJCIPMQ-UHFFFAOYSA-N bis(1,2,3,4,4a,5,6,7,8,8a-decahydronaphthalen-1-yl)silane Chemical compound C1(CCCC2CCCCC12)[SiH2]C1CCCC2CCCCC12 QTNGGWXXJCIPMQ-UHFFFAOYSA-N 0.000 description 1
- GAHSOBODSWGWHR-UHFFFAOYSA-N bis(2,2-dimethylpropyl) benzene-1,2-dicarboxylate Chemical compound CC(C)(C)COC(=O)C1=CC=CC=C1C(=O)OCC(C)(C)C GAHSOBODSWGWHR-UHFFFAOYSA-N 0.000 description 1
- ZFMQKOWCDKKBIF-UHFFFAOYSA-N bis(3,5-difluorophenyl)phosphane Chemical class FC1=CC(F)=CC(PC=2C=C(F)C=C(F)C=2)=C1 ZFMQKOWCDKKBIF-UHFFFAOYSA-N 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- FPCJKVGGYOAWIZ-UHFFFAOYSA-N butan-1-ol;titanium Chemical compound [Ti].CCCCO.CCCCO.CCCCO.CCCCO FPCJKVGGYOAWIZ-UHFFFAOYSA-N 0.000 description 1
- APKYUQFPWXLNFH-UHFFFAOYSA-M butan-1-olate titanium(4+) chloride Chemical compound [Cl-].CCCCO[Ti+](OCCCC)OCCCC APKYUQFPWXLNFH-UHFFFAOYSA-M 0.000 description 1
- DEFMLLQRTVNBOF-UHFFFAOYSA-K butan-1-olate;trichlorotitanium(1+) Chemical compound [Cl-].[Cl-].[Cl-].CCCCO[Ti+3] DEFMLLQRTVNBOF-UHFFFAOYSA-K 0.000 description 1
- VBLDUBUUQYXSCG-UHFFFAOYSA-N butan-2-ylsilane Chemical compound CCC(C)[SiH3] VBLDUBUUQYXSCG-UHFFFAOYSA-N 0.000 description 1
- OBNCKNCVKJNDBV-UHFFFAOYSA-N butanoic acid ethyl ester Natural products CCCC(=O)OCC OBNCKNCVKJNDBV-UHFFFAOYSA-N 0.000 description 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- SUMZPAWBCNVYFN-UHFFFAOYSA-N chloro(pentyl)silane Chemical compound CCCCC[SiH2]Cl SUMZPAWBCNVYFN-UHFFFAOYSA-N 0.000 description 1
- KWWYVKCQIGZPRL-UHFFFAOYSA-N chloroethene;hex-1-ene Chemical compound ClC=C.CCCCC=C KWWYVKCQIGZPRL-UHFFFAOYSA-N 0.000 description 1
- 238000004581 coalescence Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- XUCKQPJKYWZURJ-UHFFFAOYSA-N cyclohexyl(dimethoxy)silane Chemical compound CO[SiH](OC)C1CCCCC1 XUCKQPJKYWZURJ-UHFFFAOYSA-N 0.000 description 1
- LFUPEVWLMBKKAW-UHFFFAOYSA-N cyclohexyl(methyl)silane Chemical compound C[SiH2]C1CCCCC1 LFUPEVWLMBKKAW-UHFFFAOYSA-N 0.000 description 1
- SJJCABYOVIHNPZ-UHFFFAOYSA-N cyclohexyl-dimethoxy-methylsilane Chemical compound CO[Si](C)(OC)C1CCCCC1 SJJCABYOVIHNPZ-UHFFFAOYSA-N 0.000 description 1
- QEPVYYOIYSITJK-UHFFFAOYSA-N cyclohexyl-ethyl-dimethoxysilane Chemical compound CC[Si](OC)(OC)C1CCCCC1 QEPVYYOIYSITJK-UHFFFAOYSA-N 0.000 description 1
- LOXHQCGRQKIWOF-UHFFFAOYSA-N cyclohexyloxysilane Chemical compound [SiH3]OC1CCCCC1 LOXHQCGRQKIWOF-UHFFFAOYSA-N 0.000 description 1
- 125000006312 cyclopentyl amino group Chemical group [H]N(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- SSIWGPHRXRSVCD-UHFFFAOYSA-N cyclopentyl(propan-2-yl)silane Chemical compound CC(C)[SiH2]C1CCCC1 SSIWGPHRXRSVCD-UHFFFAOYSA-N 0.000 description 1
- IRRVTIDUSZWLNF-UHFFFAOYSA-N cyclopentylsilane Chemical compound [SiH3]C1CCCC1 IRRVTIDUSZWLNF-UHFFFAOYSA-N 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- DEHCLLRUWOGPJR-UHFFFAOYSA-N di(propan-2-yl)silane Chemical compound CC(C)[SiH2]C(C)C DEHCLLRUWOGPJR-UHFFFAOYSA-N 0.000 description 1
- JBSLOWBPDRZSMB-FPLPWBNLSA-N dibutyl (z)-but-2-enedioate Chemical compound CCCCOC(=O)\C=C/C(=O)OCCCC JBSLOWBPDRZSMB-FPLPWBNLSA-N 0.000 description 1
- 229940100539 dibutyl adipate Drugs 0.000 description 1
- YPENMAABQGWRBR-UHFFFAOYSA-N dibutyl(dimethoxy)silane Chemical compound CCCC[Si](OC)(OC)CCCC YPENMAABQGWRBR-UHFFFAOYSA-N 0.000 description 1
- BVXJCKRUWQUGHP-UHFFFAOYSA-N dibutylsilicon Chemical compound CCCC[Si]CCCC BVXJCKRUWQUGHP-UHFFFAOYSA-N 0.000 description 1
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 229940043279 diisopropylamine Drugs 0.000 description 1
- JVUVKQDVTIIMOD-UHFFFAOYSA-N dimethoxy(dipropyl)silane Chemical compound CCC[Si](OC)(OC)CCC JVUVKQDVTIIMOD-UHFFFAOYSA-N 0.000 description 1
- WOUUFVMQNDKHSY-UHFFFAOYSA-N dimethoxy(methyl)silane Chemical compound CO[SiH](C)OC WOUUFVMQNDKHSY-UHFFFAOYSA-N 0.000 description 1
- DWYGLGYVAMEOSL-UHFFFAOYSA-N dimethoxy(pentyl)silane Chemical compound CCCCC[SiH](OC)OC DWYGLGYVAMEOSL-UHFFFAOYSA-N 0.000 description 1
- FBSAITBEAPNWJG-UHFFFAOYSA-N dimethyl phthalate Natural products CC(=O)OC1=CC=CC=C1OC(C)=O FBSAITBEAPNWJG-UHFFFAOYSA-N 0.000 description 1
- 229910001882 dioxygen Inorganic materials 0.000 description 1
- POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 1
- OANIYCQMEVXZCJ-UHFFFAOYSA-N ditert-butyl(dimethoxy)silane Chemical compound CO[Si](OC)(C(C)(C)C)C(C)(C)C OANIYCQMEVXZCJ-UHFFFAOYSA-N 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- PJJHAYWKTHVZBL-UHFFFAOYSA-N ethyl(heptyl)silane Chemical compound CCCCCCC[SiH2]CC PJJHAYWKTHVZBL-UHFFFAOYSA-N 0.000 description 1
- MYCYHDWZOIIDRI-UHFFFAOYSA-N ethyl-dimethoxy-pentylsilane Chemical compound CCCCC[Si](CC)(OC)OC MYCYHDWZOIIDRI-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 229940014144 folate Drugs 0.000 description 1
- OVBPIULPVIDEAO-LBPRGKRZSA-N folic acid Chemical compound C=1N=C2NC(N)=NC(=O)C2=NC=1CNC1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 OVBPIULPVIDEAO-LBPRGKRZSA-N 0.000 description 1
- 235000019152 folic acid Nutrition 0.000 description 1
- 239000011724 folic acid Substances 0.000 description 1
- 235000019256 formaldehyde Nutrition 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 238000012685 gas phase polymerization Methods 0.000 description 1
- 150000004795 grignard reagents Chemical class 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- MFHGKNBDYCLVST-UHFFFAOYSA-N heptylsilane Chemical compound CCCCCCC[SiH3] MFHGKNBDYCLVST-UHFFFAOYSA-N 0.000 description 1
- GXNDYZPMZKJDSS-UHFFFAOYSA-N hex-1-ene Chemical compound CCCCC=C.CCCCC=C GXNDYZPMZKJDSS-UHFFFAOYSA-N 0.000 description 1
- WNLRTRBMVRJNCN-UHFFFAOYSA-N hexanedioic acid Natural products OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 1
- ISBXAFPBXLGRIP-UHFFFAOYSA-N hexyl(methyl)silicon Chemical compound CCCCCC[Si]C ISBXAFPBXLGRIP-UHFFFAOYSA-N 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- UWNADWZGEHDQAB-UHFFFAOYSA-N i-Pr2C2H4i-Pr2 Natural products CC(C)CCC(C)C UWNADWZGEHDQAB-UHFFFAOYSA-N 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 125000006316 iso-butyl amino group Chemical group [H]N(*)C([H])([H])C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 150000002642 lithium compounds Chemical class 0.000 description 1
- XDKQUSKHRIUJEO-UHFFFAOYSA-N magnesium;ethanolate Chemical compound [Mg+2].CC[O-].CC[O-] XDKQUSKHRIUJEO-UHFFFAOYSA-N 0.000 description 1
- WNJYXPXGUGOGBO-UHFFFAOYSA-N magnesium;propan-1-olate Chemical compound CCCO[Mg]OCCC WNJYXPXGUGOGBO-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- OKENUZUGNVCOMC-UHFFFAOYSA-K methanolate titanium(4+) trichloride Chemical compound [Cl-].[Cl-].[Cl-].CO[Ti+3] OKENUZUGNVCOMC-UHFFFAOYSA-K 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 1
- DDIZAANNODHTRB-UHFFFAOYSA-N methyl p-anisate Chemical compound COC(=O)C1=CC=C(OC)C=C1 DDIZAANNODHTRB-UHFFFAOYSA-N 0.000 description 1
- CTDFLUCDXSXGEC-UHFFFAOYSA-N methyl(dipentyl)silane Chemical compound CCCCC[SiH](C)CCCCC CTDFLUCDXSXGEC-UHFFFAOYSA-N 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 description 1
- XOSNGXNHDRYFEF-UHFFFAOYSA-N monohexyl phthalate Chemical compound CCCCCCOC(=O)C1=CC=CC=C1C(O)=O XOSNGXNHDRYFEF-UHFFFAOYSA-N 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- WZWZGEZPNHWKRW-UHFFFAOYSA-N n-(methylaminosilyl)methanamine Chemical compound CN[SiH2]NC WZWZGEZPNHWKRW-UHFFFAOYSA-N 0.000 description 1
- PFMNNAQDZLLZPJ-UHFFFAOYSA-N n-[(cyclohexylamino)-bis(ethylamino)silyl]cyclohexanamine Chemical compound C1CCCCC1N[Si](NCC)(NCC)NC1CCCCC1 PFMNNAQDZLLZPJ-UHFFFAOYSA-N 0.000 description 1
- AFHJJYWJKOGXFZ-UHFFFAOYSA-N n-[(cyclohexylamino)-bis(methylamino)silyl]cyclohexanamine Chemical compound C1CCCCC1N[Si](NC)(NC)NC1CCCCC1 AFHJJYWJKOGXFZ-UHFFFAOYSA-N 0.000 description 1
- JPNGYZGKOZEBPI-UHFFFAOYSA-N n-[(cyclopentylamino)-bis(ethylamino)silyl]cyclopentanamine Chemical compound C1CCCC1N[Si](NCC)(NCC)NC1CCCC1 JPNGYZGKOZEBPI-UHFFFAOYSA-N 0.000 description 1
- MSKGZDDMSVRAFP-UHFFFAOYSA-N n-[(cyclopentylamino)-bis(methylamino)silyl]cyclopentanamine Chemical compound C1CCCC1N[Si](NC)(NC)NC1CCCC1 MSKGZDDMSVRAFP-UHFFFAOYSA-N 0.000 description 1
- FEXGOLTVDOCOCN-UHFFFAOYSA-N n-[(cyclopentylamino)-bis(propylamino)silyl]cyclopentanamine Chemical class C1CCCC1N[Si](NCCC)(NCCC)NC1CCCC1 FEXGOLTVDOCOCN-UHFFFAOYSA-N 0.000 description 1
- RWKZXHAHLHRAIH-UHFFFAOYSA-N n-[(dipropylamino)-diethoxysilyl]-n-propylpropan-1-amine Chemical compound CCCN(CCC)[Si](OCC)(OCC)N(CCC)CCC RWKZXHAHLHRAIH-UHFFFAOYSA-N 0.000 description 1
- FMCWWGDYEUHPRS-UHFFFAOYSA-N n-[bis(1,2,3,4,4a,5,6,7,8,8a-decahydronaphthalen-1-yl)-(methylamino)silyl]methanamine Chemical compound C1CCC2CCCCC2C1[Si](NC)(NC)C1C2CCCCC2CCC1 FMCWWGDYEUHPRS-UHFFFAOYSA-N 0.000 description 1
- DOPURELLWBWOIJ-UHFFFAOYSA-N n-[bis(1,2,3,4,4a,5,6,7,8,8a-decahydronaphthalen-1-yl)-(propan-2-ylamino)silyl]propan-2-amine Chemical class C1CCC2CCCCC2C1[Si](NC(C)C)(NC(C)C)C1C2CCCCC2CCC1 DOPURELLWBWOIJ-UHFFFAOYSA-N 0.000 description 1
- XGPVTLUSMKTZFN-UHFFFAOYSA-N n-[bis(2,2-dimethylpropyl)-(propan-2-ylamino)silyl]propan-2-amine Chemical compound CC(C)N[Si](CC(C)(C)C)(CC(C)(C)C)NC(C)C XGPVTLUSMKTZFN-UHFFFAOYSA-N 0.000 description 1
- OBJRAENCQHRXAI-UHFFFAOYSA-N n-[bis(2-methylpropyl)-(propylamino)silyl]propan-1-amine Chemical compound CCCN[Si](CC(C)C)(CC(C)C)NCCC OBJRAENCQHRXAI-UHFFFAOYSA-N 0.000 description 1
- WPNPLWLFOJHXFW-UHFFFAOYSA-N n-[bis(butan-2-ylamino)-ethylsilyl]butan-2-amine Chemical compound CCC(C)N[Si](CC)(NC(C)CC)NC(C)CC WPNPLWLFOJHXFW-UHFFFAOYSA-N 0.000 description 1
- QKAFVOMQWANZFT-UHFFFAOYSA-N n-[bis(butylamino)-propan-2-ylsilyl]butan-1-amine Chemical compound CCCCN[Si](NCCCC)(NCCCC)C(C)C QKAFVOMQWANZFT-UHFFFAOYSA-N 0.000 description 1
- FFBNRSXCPRRDBX-UHFFFAOYSA-N n-[bis(cyclopentylamino)-(methylamino)silyl]cyclopentanamine Chemical compound C1CCCC1N[Si](NC1CCCC1)(NC)NC1CCCC1 FFBNRSXCPRRDBX-UHFFFAOYSA-N 0.000 description 1
- OLOIUDZHGQISEM-UHFFFAOYSA-N n-[bis(cyclopentylamino)-ethylsilyl]cyclopentanamine Chemical compound C1CCCC1N[Si](NC1CCCC1)(CC)NC1CCCC1 OLOIUDZHGQISEM-UHFFFAOYSA-N 0.000 description 1
- UYFGBHQAIBGRBR-UHFFFAOYSA-N n-[bis(cyclopentylamino)-propan-2-ylsilyl]cyclopentanamine Chemical compound C1CCCC1N[Si](NC1CCCC1)(C(C)C)NC1CCCC1 UYFGBHQAIBGRBR-UHFFFAOYSA-N 0.000 description 1
- CMLZPUMZQYLAID-UHFFFAOYSA-N n-[bis(dibutylamino)-(methylamino)silyl]-n-butylbutan-1-amine Chemical compound CCCCN(CCCC)[Si](NC)(N(CCCC)CCCC)N(CCCC)CCCC CMLZPUMZQYLAID-UHFFFAOYSA-N 0.000 description 1
- BZMDKFZYAKOPAZ-UHFFFAOYSA-N n-[bis(diethylamino)-(methylamino)silyl]-n-ethylethanamine Chemical compound CCN(CC)[Si](NC)(N(CC)CC)N(CC)CC BZMDKFZYAKOPAZ-UHFFFAOYSA-N 0.000 description 1
- QOQPQDVXMIVQDF-UHFFFAOYSA-N n-[bis(dimethylamino)-methoxysilyl]-n-methylmethanamine Chemical compound CO[Si](N(C)C)(N(C)C)N(C)C QOQPQDVXMIVQDF-UHFFFAOYSA-N 0.000 description 1
- BXUHWAPDLTXJLX-UHFFFAOYSA-N n-[bis(dipropylamino)-(propylamino)silyl]propan-1-amine Chemical compound CCCN[Si](NCCC)(N(CCC)CCC)N(CCC)CCC BXUHWAPDLTXJLX-UHFFFAOYSA-N 0.000 description 1
- ODVDDQFBQGTLIA-UHFFFAOYSA-N n-[bis(ethenyl)-(ethylamino)silyl]ethanamine Chemical compound CCN[Si](C=C)(C=C)NCC ODVDDQFBQGTLIA-UHFFFAOYSA-N 0.000 description 1
- GWOPLFQULNLCQB-UHFFFAOYSA-N n-[bis(ethenyl)-(methylamino)silyl]methanamine Chemical compound CN[Si](NC)(C=C)C=C GWOPLFQULNLCQB-UHFFFAOYSA-N 0.000 description 1
- VUHOGGWHQQMNLA-UHFFFAOYSA-N n-[bis(ethylamino)-(methylamino)silyl]ethanamine Chemical compound CCN[Si](NC)(NCC)NCC VUHOGGWHQQMNLA-UHFFFAOYSA-N 0.000 description 1
- XNPLSBORJGBACM-UHFFFAOYSA-N n-[bis(ethylamino)-(propylamino)silyl]propan-1-amine Chemical compound CCCN[Si](NCC)(NCC)NCCC XNPLSBORJGBACM-UHFFFAOYSA-N 0.000 description 1
- WBRWEYCGDXVTSR-UHFFFAOYSA-N n-[bis(ethylamino)-methylsilyl]ethanamine Chemical compound CCN[Si](C)(NCC)NCC WBRWEYCGDXVTSR-UHFFFAOYSA-N 0.000 description 1
- NIAPCAWYRDQYQU-UHFFFAOYSA-N n-[bis(ethylamino)-propylsilyl]ethanamine Chemical compound CCC[Si](NCC)(NCC)NCC NIAPCAWYRDQYQU-UHFFFAOYSA-N 0.000 description 1
- PUECIUOSPLBMOK-UHFFFAOYSA-N n-[bis(methylamino)-(propylamino)silyl]propan-1-amine Chemical compound CCCN[Si](NC)(NC)NCCC PUECIUOSPLBMOK-UHFFFAOYSA-N 0.000 description 1
- CEXQTVZDFRXEPC-UHFFFAOYSA-N n-[bis(methylamino)-propylsilyl]methanamine Chemical compound CCC[Si](NC)(NC)NC CEXQTVZDFRXEPC-UHFFFAOYSA-N 0.000 description 1
- ADEHLICTSGPCBH-UHFFFAOYSA-N n-[bis(tert-butylamino)-(propylamino)silyl]-2-methylpropan-2-amine Chemical compound CCCN[Si](NC(C)(C)C)(NC(C)(C)C)NC(C)(C)C ADEHLICTSGPCBH-UHFFFAOYSA-N 0.000 description 1
- LSDCHMLWMHMEQC-UHFFFAOYSA-N n-[butan-2-yl-bis(methylamino)silyl]-2-methylpropan-2-amine Chemical compound CCC(C)[Si](NC)(NC)NC(C)(C)C LSDCHMLWMHMEQC-UHFFFAOYSA-N 0.000 description 1
- RPXSFIJTZUJLPZ-UHFFFAOYSA-N n-[butan-2-yl-ethyl-(ethylamino)silyl]ethanamine Chemical compound CCN[Si](CC)(NCC)C(C)CC RPXSFIJTZUJLPZ-UHFFFAOYSA-N 0.000 description 1
- WMJDERSEMQITGZ-UHFFFAOYSA-N n-[butan-2-yl-methyl-(methylamino)silyl]methanamine Chemical compound CCC(C)[Si](C)(NC)NC WMJDERSEMQITGZ-UHFFFAOYSA-N 0.000 description 1
- SBCPHTKZAVZXSU-UHFFFAOYSA-N n-[butan-2-yl-methyl-(propan-2-ylamino)silyl]propan-2-amine Chemical compound CCC(C)[Si](C)(NC(C)C)NC(C)C SBCPHTKZAVZXSU-UHFFFAOYSA-N 0.000 description 1
- DVOXRMWWRYOOKW-UHFFFAOYSA-N n-[butyl-bis(methylamino)silyl]-2-methylpropan-1-amine Chemical compound CCCC[Si](NC)(NC)NCC(C)C DVOXRMWWRYOOKW-UHFFFAOYSA-N 0.000 description 1
- VXEACTXZCNNLAU-UHFFFAOYSA-N n-[butyl-bis(methylamino)silyl]-2-methylpropan-2-amine Chemical compound CCCC[Si](NC)(NC)NC(C)(C)C VXEACTXZCNNLAU-UHFFFAOYSA-N 0.000 description 1
- RJILRZXYMVSTLO-UHFFFAOYSA-N n-[butyl-bis(methylamino)silyl]methanamine Chemical compound CCCC[Si](NC)(NC)NC RJILRZXYMVSTLO-UHFFFAOYSA-N 0.000 description 1
- CSUOBDUVAYARMM-UHFFFAOYSA-N n-[butylamino-bis(ethylamino)silyl]butan-1-amine Chemical compound CCCCN[Si](NCC)(NCC)NCCCC CSUOBDUVAYARMM-UHFFFAOYSA-N 0.000 description 1
- BCOZYAGHMVIQEV-UHFFFAOYSA-N n-[cyclohexyl-bis(methylamino)silyl]-2-methylpropan-1-amine Chemical compound CC(C)CN[Si](NC)(NC)C1CCCCC1 BCOZYAGHMVIQEV-UHFFFAOYSA-N 0.000 description 1
- MTNAQMHADVULOM-UHFFFAOYSA-N n-[cyclohexyl-bis(propan-2-ylamino)silyl]propan-2-amine Chemical compound CC(C)N[Si](NC(C)C)(NC(C)C)C1CCCCC1 MTNAQMHADVULOM-UHFFFAOYSA-N 0.000 description 1
- VLGQXZNPGOBPLE-UHFFFAOYSA-N n-[cyclohexyl-methyl-(methylamino)silyl]methanamine Chemical compound CN[Si](C)(NC)C1CCCCC1 VLGQXZNPGOBPLE-UHFFFAOYSA-N 0.000 description 1
- LKILVFFIJZZIIZ-UHFFFAOYSA-N n-[cyclopentyl-bis(methylamino)silyl]-2-methylpropan-2-amine Chemical compound CC(C)(C)N[Si](NC)(NC)C1CCCC1 LKILVFFIJZZIIZ-UHFFFAOYSA-N 0.000 description 1
- QZRIKCMFKVVRHE-UHFFFAOYSA-N n-[cyclopentyl-methyl-(methylamino)silyl]methanamine Chemical compound CN[Si](C)(NC)C1CCCC1 QZRIKCMFKVVRHE-UHFFFAOYSA-N 0.000 description 1
- IGUISAYAGSILJH-UHFFFAOYSA-N n-[di(butan-2-yl)-(methylamino)silyl]methanamine Chemical compound CCC(C)[Si](NC)(NC)C(C)CC IGUISAYAGSILJH-UHFFFAOYSA-N 0.000 description 1
- IISPWTRMASASRK-UHFFFAOYSA-N n-[di(butan-2-yl)-(propylamino)silyl]propan-1-amine Chemical compound CCCN[Si](C(C)CC)(C(C)CC)NCCC IISPWTRMASASRK-UHFFFAOYSA-N 0.000 description 1
- CTTRVCJAERXZEH-UHFFFAOYSA-N n-[di(isoquinolin-1-yl)-(methylamino)silyl]propan-1-amine Chemical compound C1=CC=C2C([Si](NC)(C=3C4=CC=CC=C4C=CN=3)NCCC)=NC=CC2=C1 CTTRVCJAERXZEH-UHFFFAOYSA-N 0.000 description 1
- JJJSUGHCNIDTET-UHFFFAOYSA-N n-[dibenzyl-(propan-2-ylamino)silyl]propan-2-amine Chemical compound C=1C=CC=CC=1C[Si](NC(C)C)(NC(C)C)CC1=CC=CC=C1 JJJSUGHCNIDTET-UHFFFAOYSA-N 0.000 description 1
- DXMDRXMOKDKVAP-UHFFFAOYSA-N n-[dibutyl(propylamino)silyl]propan-1-amine Chemical compound CCCC[Si](CCCC)(NCCC)NCCC DXMDRXMOKDKVAP-UHFFFAOYSA-N 0.000 description 1
- FBAARQPAKSSLKI-UHFFFAOYSA-N n-[dicyclohexyl(propylamino)silyl]propan-1-amine Chemical compound C1CCCCC1[Si](NCCC)(NCCC)C1CCCCC1 FBAARQPAKSSLKI-UHFFFAOYSA-N 0.000 description 1
- JVOJYDJGTRRTKS-UHFFFAOYSA-N n-[dicyclohexyl-(propan-2-ylamino)silyl]propan-2-amine Chemical compound C1CCCCC1[Si](NC(C)C)(NC(C)C)C1CCCCC1 JVOJYDJGTRRTKS-UHFFFAOYSA-N 0.000 description 1
- ZAWZXRGLXVKVTF-UHFFFAOYSA-N n-[dicyclopentyl(methylamino)silyl]propan-1-amine Chemical compound C1CCCC1[Si](NC)(NCCC)C1CCCC1 ZAWZXRGLXVKVTF-UHFFFAOYSA-N 0.000 description 1
- SWOCMXXRGFDCOP-UHFFFAOYSA-N n-[diethoxy(propyl)silyl]-n-propan-2-ylpropan-2-amine Chemical compound CCC[Si](OCC)(OCC)N(C(C)C)C(C)C SWOCMXXRGFDCOP-UHFFFAOYSA-N 0.000 description 1
- WNPFBMPYQWFHOJ-UHFFFAOYSA-N n-[diethyl(methylamino)silyl]methanamine Chemical compound CC[Si](CC)(NC)NC WNPFBMPYQWFHOJ-UHFFFAOYSA-N 0.000 description 1
- INRSGFWUIBYFGX-UHFFFAOYSA-N n-[dimethyl(methylamino)silyl]methanamine Chemical compound CN[Si](C)(C)NC INRSGFWUIBYFGX-UHFFFAOYSA-N 0.000 description 1
- VOFDOUONNKTMRU-UHFFFAOYSA-N n-[dimethyl(propylamino)silyl]propan-1-amine Chemical compound CCCN[Si](C)(C)NCCC VOFDOUONNKTMRU-UHFFFAOYSA-N 0.000 description 1
- UJQCWMZDDOWCCD-UHFFFAOYSA-N n-[dimethylamino-methyl-(methylamino)silyl]methanamine Chemical compound CN[Si](C)(NC)N(C)C UJQCWMZDDOWCCD-UHFFFAOYSA-N 0.000 description 1
- AITIKUVVPMCSPG-UHFFFAOYSA-N n-[diphenyl-(propan-2-ylamino)silyl]propan-2-amine Chemical compound C=1C=CC=CC=1[Si](NC(C)C)(NC(C)C)C1=CC=CC=C1 AITIKUVVPMCSPG-UHFFFAOYSA-N 0.000 description 1
- JUUUXMQFQCQITF-UHFFFAOYSA-N n-[ditert-butyl(methylamino)silyl]methanamine Chemical compound CN[Si](NC)(C(C)(C)C)C(C)(C)C JUUUXMQFQCQITF-UHFFFAOYSA-N 0.000 description 1
- NMTAMKZOXOXJQJ-UHFFFAOYSA-N n-[ethyl-(ethylamino)-methylsilyl]ethanamine Chemical compound CCN[Si](C)(CC)NCC NMTAMKZOXOXJQJ-UHFFFAOYSA-N 0.000 description 1
- PAHMPBMANCIYCT-UHFFFAOYSA-N n-[ethyl-bis(methylamino)silyl]-2-methylpropan-2-amine Chemical compound CC[Si](NC)(NC)NC(C)(C)C PAHMPBMANCIYCT-UHFFFAOYSA-N 0.000 description 1
- XUXWCSPEXIQQIV-UHFFFAOYSA-N n-[ethyl-bis(methylamino)silyl]-n-methylbutan-1-amine Chemical compound CCCCN(C)[Si](CC)(NC)NC XUXWCSPEXIQQIV-UHFFFAOYSA-N 0.000 description 1
- IXIKKCKHXYGOAD-UHFFFAOYSA-N n-[ethyl-bis(methylamino)silyl]-n-methylcyclopentanamine Chemical compound CC[Si](NC)(NC)N(C)C1CCCC1 IXIKKCKHXYGOAD-UHFFFAOYSA-N 0.000 description 1
- HDEBPOSKOKVGBE-UHFFFAOYSA-N n-[ethyl-bis(methylamino)silyl]-n-propylpropan-1-amine Chemical compound CCCN(CCC)[Si](CC)(NC)NC HDEBPOSKOKVGBE-UHFFFAOYSA-N 0.000 description 1
- AWFDOFHAOJOTPS-UHFFFAOYSA-N n-[ethyl-methyl-(methylamino)silyl]methanamine Chemical compound CC[Si](C)(NC)NC AWFDOFHAOJOTPS-UHFFFAOYSA-N 0.000 description 1
- NGAVXENYOVMGDJ-UHFFFAOYSA-N n-[ethylamino(dimethyl)silyl]ethanamine Chemical compound CCN[Si](C)(C)NCC NGAVXENYOVMGDJ-UHFFFAOYSA-N 0.000 description 1
- DCYZIKSTWSCJJV-UHFFFAOYSA-N n-[ethylamino-bis(2-methylpropyl)silyl]ethanamine Chemical compound CCN[Si](CC(C)C)(CC(C)C)NCC DCYZIKSTWSCJJV-UHFFFAOYSA-N 0.000 description 1
- QGMVMHHWDYZAHD-UHFFFAOYSA-N n-[ethylamino-bis(methylamino)silyl]ethanamine Chemical compound CCN[Si](NC)(NC)NCC QGMVMHHWDYZAHD-UHFFFAOYSA-N 0.000 description 1
- PEXMKRNOXXXMLY-UHFFFAOYSA-N n-[methyl-(methylamino)-phenylsilyl]methanamine Chemical compound CN[Si](C)(NC)C1=CC=CC=C1 PEXMKRNOXXXMLY-UHFFFAOYSA-N 0.000 description 1
- ZTCGNJUJJTYQCZ-UHFFFAOYSA-N n-[methyl-bis(methylamino)silyl]-n-propylpropan-1-amine Chemical compound CCCN(CCC)[Si](C)(NC)NC ZTCGNJUJJTYQCZ-UHFFFAOYSA-N 0.000 description 1
- VVKLYRZRWCHXCG-UHFFFAOYSA-N n-[methylamino-bis(2-methylpropyl)silyl]methanamine Chemical compound CC(C)C[Si](NC)(CC(C)C)NC VVKLYRZRWCHXCG-UHFFFAOYSA-N 0.000 description 1
- OLMNIMMBZCBGPU-UHFFFAOYSA-N n-[methylamino-bis(propylamino)silyl]propan-1-amine Chemical compound CCCN[Si](NC)(NCCC)NCCC OLMNIMMBZCBGPU-UHFFFAOYSA-N 0.000 description 1
- NQIGLKUFXMMKCL-UHFFFAOYSA-N n-[methylamino-di(propan-2-yl)silyl]methanamine Chemical compound CN[Si](NC)(C(C)C)C(C)C NQIGLKUFXMMKCL-UHFFFAOYSA-N 0.000 description 1
- TUQCDTFVGVCAMH-UHFFFAOYSA-N n-[propyl-bis(propylamino)silyl]propan-1-amine Chemical compound CCCN[Si](CCC)(NCCC)NCCC TUQCDTFVGVCAMH-UHFFFAOYSA-N 0.000 description 1
- RBLLDZXUILVBNA-UHFFFAOYSA-N n-[tris(dimethylamino)silyl]methanamine Chemical compound CN[Si](N(C)C)(N(C)C)N(C)C RBLLDZXUILVBNA-UHFFFAOYSA-N 0.000 description 1
- ZKEHBPZHLCBLTE-UHFFFAOYSA-N n-[tris(dimethylamino)silyl]propan-1-amine Chemical compound CCCN[Si](N(C)C)(N(C)C)N(C)C ZKEHBPZHLCBLTE-UHFFFAOYSA-N 0.000 description 1
- JWJYZMSZUGCIHO-UHFFFAOYSA-N n-[tris(ethylamino)silyl]ethanamine Chemical compound CCN[Si](NCC)(NCC)NCC JWJYZMSZUGCIHO-UHFFFAOYSA-N 0.000 description 1
- FBEYTISXUBWWSZ-UHFFFAOYSA-N n-[tris(ethylamino)silyl]propan-1-amine Chemical compound CCCN[Si](NCC)(NCC)NCC FBEYTISXUBWWSZ-UHFFFAOYSA-N 0.000 description 1
- CCGPNQNPVXLPEP-UHFFFAOYSA-N n-[tris(methylamino)silyl]ethanamine Chemical compound CCN[Si](NC)(NC)NC CCGPNQNPVXLPEP-UHFFFAOYSA-N 0.000 description 1
- UMHFNGOXBUYFSH-UHFFFAOYSA-N n-[tris(methylamino)silyl]propan-1-amine Chemical compound CCCN[Si](NC)(NC)NC UMHFNGOXBUYFSH-UHFFFAOYSA-N 0.000 description 1
- FYVBLNSNANWPEN-UHFFFAOYSA-N n-[tris(propylamino)silyl]butan-1-amine Chemical compound CCCCN[Si](NCCC)(NCCC)NCCC FYVBLNSNANWPEN-UHFFFAOYSA-N 0.000 description 1
- VWWBNDHSUOTMTO-UHFFFAOYSA-N n-[tris(propylamino)silyl]cyclohexanamine Chemical compound CCCN[Si](NCCC)(NCCC)NC1CCCCC1 VWWBNDHSUOTMTO-UHFFFAOYSA-N 0.000 description 1
- JAKFTCMEIAFVLU-UHFFFAOYSA-N n-[tris(propylamino)silyl]propan-1-amine Chemical compound CCCN[Si](NCCC)(NCCC)NCCC JAKFTCMEIAFVLU-UHFFFAOYSA-N 0.000 description 1
- NIUXEDDHUNBBSQ-UHFFFAOYSA-N n-butyl-n-[(dibutylamino)-bis(ethylamino)silyl]butan-1-amine Chemical compound CCCCN(CCCC)[Si](NCC)(NCC)N(CCCC)CCCC NIUXEDDHUNBBSQ-UHFFFAOYSA-N 0.000 description 1
- UKPVTBVQTUXZMW-UHFFFAOYSA-N n-butyl-n-[(dibutylamino)-bis(methylamino)silyl]butan-1-amine Chemical compound CCCCN(CCCC)[Si](NC)(NC)N(CCCC)CCCC UKPVTBVQTUXZMW-UHFFFAOYSA-N 0.000 description 1
- SIYKROHRYPZQGF-UHFFFAOYSA-N n-butyl-n-[(dibutylamino)-diethoxysilyl]butan-1-amine Chemical compound CCCCN(CCCC)[Si](OCC)(OCC)N(CCCC)CCCC SIYKROHRYPZQGF-UHFFFAOYSA-N 0.000 description 1
- XMGZCLRFISWIAY-UHFFFAOYSA-N n-butyl-n-trimethoxysilylbutan-1-amine Chemical compound CCCCN([Si](OC)(OC)OC)CCCC XMGZCLRFISWIAY-UHFFFAOYSA-N 0.000 description 1
- RNXPQMYKWBUNQD-UHFFFAOYSA-N n-cyclohexyl-n-[(dicyclohexylamino)-bis(methylamino)silyl]cyclohexanamine Chemical compound C1CCCCC1N(C1CCCCC1)[Si](NC)(NC)N(C1CCCCC1)C1CCCCC1 RNXPQMYKWBUNQD-UHFFFAOYSA-N 0.000 description 1
- WOKGGFROYHOMPS-UHFFFAOYSA-N n-cyclohexyl-n-[(dicyclohexylamino)-bis(propylamino)silyl]cyclohexanamine Chemical class C1CCCCC1N(C1CCCCC1)[Si](NCCC)(NCCC)N(C1CCCCC1)C1CCCCC1 WOKGGFROYHOMPS-UHFFFAOYSA-N 0.000 description 1
- IOUUQWASUFSYAR-UHFFFAOYSA-N n-cyclohexyl-n-[tris(propylamino)silyl]cyclohexanamine Chemical compound C1CCCCC1N([Si](NCCC)(NCCC)NCCC)C1CCCCC1 IOUUQWASUFSYAR-UHFFFAOYSA-N 0.000 description 1
- XBTJQYWDPSYMNE-UHFFFAOYSA-N n-cyclohexyl-n-trimethoxysilylcyclohexanamine Chemical compound C1CCCCC1N([Si](OC)(OC)OC)C1CCCCC1 XBTJQYWDPSYMNE-UHFFFAOYSA-N 0.000 description 1
- IKJOZPXHKARMFM-UHFFFAOYSA-N n-cyclopentyl-n-[(dicyclopentylamino)-bis(ethylamino)silyl]cyclopentanamine Chemical compound C1CCCC1N(C1CCCC1)[Si](NCC)(NCC)N(C1CCCC1)C1CCCC1 IKJOZPXHKARMFM-UHFFFAOYSA-N 0.000 description 1
- JKRMKDOWEPAYFK-UHFFFAOYSA-N n-cyclopentyl-n-[(dicyclopentylamino)-bis(methylamino)silyl]cyclopentanamine Chemical compound C1CCCC1N(C1CCCC1)[Si](NC)(NC)N(C1CCCC1)C1CCCC1 JKRMKDOWEPAYFK-UHFFFAOYSA-N 0.000 description 1
- SGLGTQYWDWTBOA-UHFFFAOYSA-N n-cyclopentyl-n-[(dicyclopentylamino)-bis(propylamino)silyl]cyclopentanamine Chemical class C1CCCC1N(C1CCCC1)[Si](NCCC)(NCCC)N(C1CCCC1)C1CCCC1 SGLGTQYWDWTBOA-UHFFFAOYSA-N 0.000 description 1
- QMRUGGSZLNAJEO-UHFFFAOYSA-N n-cyclopentyl-n-[(dicyclopentylamino)-dimethoxysilyl]cyclopentanamine Chemical compound C1CCCC1N(C1CCCC1)[Si](OC)(OC)N(C1CCCC1)C1CCCC1 QMRUGGSZLNAJEO-UHFFFAOYSA-N 0.000 description 1
- WYPFENZEVIAUFX-UHFFFAOYSA-N n-ethyl-n-[ethyl-bis(methylamino)silyl]cyclohexanamine Chemical compound CC[Si](NC)(NC)N(CC)C1CCCCC1 WYPFENZEVIAUFX-UHFFFAOYSA-N 0.000 description 1
- FFFWXXHMTSGVEW-UHFFFAOYSA-N n-ethyl-n-[ethyl-bis(methylamino)silyl]cyclopentanamine Chemical compound CC[Si](NC)(NC)N(CC)C1CCCC1 FFFWXXHMTSGVEW-UHFFFAOYSA-N 0.000 description 1
- VWHUCVGURFQYHW-UHFFFAOYSA-N n-ethyl-n-[methyl-bis(methylamino)silyl]butan-2-amine Chemical compound CCC(C)N(CC)[Si](C)(NC)NC VWHUCVGURFQYHW-UHFFFAOYSA-N 0.000 description 1
- BFJXBVJCRWAHAL-UHFFFAOYSA-N n-ethyl-n-[tris(methylamino)silyl]ethanamine Chemical class CCN(CC)[Si](NC)(NC)NC BFJXBVJCRWAHAL-UHFFFAOYSA-N 0.000 description 1
- PIERHESCIKKKCI-UHFFFAOYSA-N n-methyl-n-[methyl-bis(methylamino)silyl]butan-1-amine Chemical compound CCCCN(C)[Si](C)(NC)NC PIERHESCIKKKCI-UHFFFAOYSA-N 0.000 description 1
- YCTDHYWASSEQNY-UHFFFAOYSA-N n-methyl-n-[methyl-bis(methylamino)silyl]cyclohexanamine Chemical compound CN[Si](C)(NC)N(C)C1CCCCC1 YCTDHYWASSEQNY-UHFFFAOYSA-N 0.000 description 1
- LCZOTJBYXHMHQS-UHFFFAOYSA-N n-methyl-n-[methyl-bis(methylamino)silyl]propan-1-amine Chemical compound CCCN(C)[Si](C)(NC)NC LCZOTJBYXHMHQS-UHFFFAOYSA-N 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- HYWMHUHLWCJXBR-UHFFFAOYSA-N n-propan-2-yl-n-[tris(ethylamino)silyl]propan-2-amine Chemical compound CCN[Si](NCC)(NCC)N(C(C)C)C(C)C HYWMHUHLWCJXBR-UHFFFAOYSA-N 0.000 description 1
- PRRAJAJGOZGWFT-UHFFFAOYSA-N n-propyl-n-trimethoxysilylpropan-1-amine Chemical compound CCCN(CCC)[Si](OC)(OC)OC PRRAJAJGOZGWFT-UHFFFAOYSA-N 0.000 description 1
- OMWJVPJRPZHTED-UHFFFAOYSA-N n-tert-butyl-2-methyl-n-[tris(ethylamino)silyl]propan-2-amine Chemical compound CCN[Si](NCC)(NCC)N(C(C)(C)C)C(C)(C)C OMWJVPJRPZHTED-UHFFFAOYSA-N 0.000 description 1
- CATWEXRJGNBIJD-UHFFFAOYSA-N n-tert-butyl-2-methylpropan-2-amine Chemical compound CC(C)(C)NC(C)(C)C CATWEXRJGNBIJD-UHFFFAOYSA-N 0.000 description 1
- VEQFZRHYRCKMEQ-UHFFFAOYSA-N n-tert-butyl-n-[(ditert-butylamino)-bis(methylamino)silyl]-2-methylpropan-2-amine Chemical compound CC(C)(C)N(C(C)(C)C)[Si](NC)(NC)N(C(C)(C)C)C(C)(C)C VEQFZRHYRCKMEQ-UHFFFAOYSA-N 0.000 description 1
- PLVGKAORDVCZIC-UHFFFAOYSA-N n-tris(dipropylamino)silylpropan-1-amine Chemical compound CCCN[Si](N(CCC)CCC)(N(CCC)CCC)N(CCC)CCC PLVGKAORDVCZIC-UHFFFAOYSA-N 0.000 description 1
- QFLHGGCNMCCJKI-UHFFFAOYSA-N n-tris(hexylamino)silylhexan-1-amine Chemical compound CCCCCCN[Si](NCCCCCC)(NCCCCCC)NCCCCCC QFLHGGCNMCCJKI-UHFFFAOYSA-N 0.000 description 1
- KYZRKVYSFGRLHP-UHFFFAOYSA-N n-tris[di(propan-2-yl)amino]silylpropan-1-amine Chemical compound CCCN[Si](N(C(C)C)C(C)C)(N(C(C)C)C(C)C)N(C(C)C)C(C)C KYZRKVYSFGRLHP-UHFFFAOYSA-N 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 1
- 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
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- PARWUHTVGZSQPD-UHFFFAOYSA-N phenylsilane Chemical compound [SiH3]C1=CC=CC=C1 PARWUHTVGZSQPD-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Substances OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 1
- 229920002120 photoresistant polymer Polymers 0.000 description 1
- 125000005498 phthalate group Chemical class 0.000 description 1
- 150000003021 phthalic acid derivatives Chemical class 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 150000004032 porphyrins Chemical class 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 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
- 238000000926 separation method Methods 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000005049 silicon tetrachloride Substances 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000012756 surface treatment agent Substances 0.000 description 1
- LXEJRKJRKIFVNY-UHFFFAOYSA-N terephthaloyl chloride Chemical compound ClC(=O)C1=CC=C(C(Cl)=O)C=C1 LXEJRKJRKIFVNY-UHFFFAOYSA-N 0.000 description 1
- PUGUQINMNYINPK-UHFFFAOYSA-N tert-butyl 4-(2-chloroacetyl)piperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCN(C(=O)CCl)CC1 PUGUQINMNYINPK-UHFFFAOYSA-N 0.000 description 1
- LOWQVRVWHXEMTR-UHFFFAOYSA-N tert-butyl(2-methylpropyl)silane Chemical compound CC(C)C[SiH2]C(C)(C)C LOWQVRVWHXEMTR-UHFFFAOYSA-N 0.000 description 1
- UFHILTCGAOPTOV-UHFFFAOYSA-N tetrakis(ethenyl)silane Chemical compound C=C[Si](C=C)(C=C)C=C UFHILTCGAOPTOV-UHFFFAOYSA-N 0.000 description 1
- 229920002725 thermoplastic elastomer Polymers 0.000 description 1
- UBZYKBZMAMTNKW-UHFFFAOYSA-J titanium tetrabromide Chemical compound Br[Ti](Br)(Br)Br UBZYKBZMAMTNKW-UHFFFAOYSA-J 0.000 description 1
- NLLZTRMHNHVXJJ-UHFFFAOYSA-J titanium tetraiodide Chemical compound I[Ti](I)(I)I NLLZTRMHNHVXJJ-UHFFFAOYSA-J 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 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
- PKRKCDBTXBGLKV-UHFFFAOYSA-N tris(ethenyl)-methylsilane Chemical compound C=C[Si](C)(C=C)C=C PKRKCDBTXBGLKV-UHFFFAOYSA-N 0.000 description 1
- 229960003732 tyramine Drugs 0.000 description 1
- 125000002948 undecyl 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])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- 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
-
- 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
- C08F10/00—Homopolymers and copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
-
- 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
- C08F110/00—Homopolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
- C08F110/04—Monomers containing three or four carbon atoms
- C08F110/06—Propene
Definitions
- the present invention proposes a novel aminosilane compound, in particular, a novel organic silicon compound which does not contain any one S 1 -OR bond, which has been essential as a conventional catalyst component for polymerization of olefins,
- the present invention relates to a catalyst component and a catalyst for polymerization of olefins used, and a method for producing a polymer of olefins using the same.
- a method has been proposed which specifically polymerizes olefins having a carbon number of 3 or more using a catalyst comprising a combination with an organic silicon compound having a sulfur-containing S i-O-C bond.
- these methods are not necessarily sufficient to obtain high stereoregular polymers in high yield, and further improvement has been desired.
- Patent Document 3 Japanese Patent Application Laid-Open No. 6-3010
- a process for the polymerization of propylene pyrene has been proposed.
- Patent Document 4 Japanese Patent Application Laid-Open No. H01-35406
- titanium tetrachloride is brought into contact with a suspension formed of methoxymagnesium and alkylbenzene, and then chlorite phthalate is produced.
- a solid product is obtained by adding and reacting to obtain a solid product, which is further prepared by contacting the solid product with titanium tetrachloride in the presence of alkylbenzene, an organoaluminum compound and an organosilicon compound.
- a catalyst for propylene pyrene comprising the same and a process for polymerizing propylene in the presence of the catalyst have been proposed.
- polymers obtained by using the above-mentioned catalyst are used in various applications such as containers and films as well as molded articles such as automobiles or home appliances. These are melted and pelletized from the polymer powder obtained by polymerization, and then molded by various molding machines, particularly when injection molding is used to produce large-sized molded articles.
- a high melt melt rate one rate, MFR
- MFR one rate
- an olefin based thermoplastic elastomer 1 (hereinafter referred to as “TPO”) Production of a copolymer only necessary for production b, b
- TPO olefin based thermoplastic elastomer 1
- the melt flow rate at the homopolymerization stage may be required to have a value of 200 or more in order to keep the size large and to make the injection molding squeaky, so the melt flow rate is increased while maintaining the high stereoregularity of the polymer.
- the melt flow rate is largely dependent on the molecular weight of the polymer. It is common practice in the art to add hydrogen as a molecular weight regulator for the resulting polymer during the polymerization of propylene. At this time, when producing a low molecular weight polymer, that is, usually adding a large amount of hydrogen to produce a polymer with a high melt flow rate, it is particularly important for the pressure resistance of the reactor for the pressure resistance of the reactor because of its safety. There is a limit, and the amount of hydrogen that can be added is also limited. '
- Patent Document 5 discloses a compound represented by S i (OR 1 ) 3 (NR 2 R 3 ) as a catalyst component for the polymerization of olephenes. It is disclosed that a polymer having high melt flow rate and high stereoregularity can be produced by using the compound as mentioned above, and some effects are listed.
- Patent Document 1 Japanese Patent Application Laid-Open No. 5 7 6 3 3 10 0 (Claims)
- an object of the present invention is to highly maintain the stereoregularity and the yield of the polymer, and to add a high melt flow rate by adding a small amount of hydrogen.
- An aminosilane compound suitable as a catalyst component for polymerization of olefins having good hydrogen response, a catalyst component for polymerization and a catalyst, and a method for producing a polymer of olefin using the same is an aminosilane compound suitable as a catalyst component for polymerization of olefins having good hydrogen response, a catalyst component for polymerization and a catalyst, and a method for producing a polymer of olefin using the same . Disclosure of the invention
- R 1 is a linear or branched alkyl group having 3 to 5 carbon atoms or a cyclic pentyl group, which may be the same or different, and R 2 is a methyl group or an ethyl group).
- the present invention provides an aminosilane compound. Further, the present invention provides the following general formula (2) ′; R 3 n S i (NR 4 R 5 ) 4 _ n (2)
- R 3 represents a linear or branched alkyl group having 1 to 20 carbon atoms, a cycloalkyl group and derivatives thereof, a Biel group, a falyl group, or a aralkyl group, which may be the same or different
- R 4 Is a hydrogen atom, a straight chain having 1 to 2 carbon atoms, a branched alkyl group, a cycloalkyl group or a derivative thereof, a buryl group, an aryl group, or an aryl group, which may be the same or different
- R 5 is a linear or branched alkyl group having 1 to 20 carbon atoms, a cycloalkyl group and derivatives thereof, a bluyl group, a falyl group or a falarky group, which may be the same or different
- R 4 and R 5 are N may be bonded to form a ring
- n is an integer of 0 or 1 to 3
- R 3 represents a linear or branched alkyl group having 1 to 20 carbon atoms, a cycloalkyl group or a derivative thereof, a bule group, an aryl group or an aryl group, which may be the same or different;
- 4 is a hydrogen atom, a linear or branched alkyl group having 1 to 2 carbon atoms 0, cycloalkyl groups and their induction body, Bulle group, Ariru group, a Ararukiru group, the same or different may be
- R 5 is A linear or branched alkyl group having 1 to 20 carbon atoms, a cycloalkyl group and derivatives thereof, a vinyl group, a aryl group, and a aralkyl group, which may be the same or different, and R 4 and R 5 are bonded together A ring may be formed, n is an integer of 0 or 1 to 3, and at least one of NR 4 R 5 groups is a secondary amino group.
- Orefin class It provides a polymerization catalyst. Further, the present invention relates to an olefene as described above, wherein The present invention provides a method for producing a olefins polymer, which comprises polymerizing an olefin.
- novel aminosilane compound of the present invention and the specific aminosilane compound when used as a catalyst component for polymerization of olefins, can maintain a higher degree of polymer stereoregularity and yield than conventional catalysts, and add a small amount of hydrogen
- the effect of obtaining high melt flow rate (hereinafter simply referred to as “hydrogen response”) is obtained. Therefore, due to the ability to reduce the amount of hydrogen used during polymerization and the high activity of the catalyst, it can provide general-purpose polyolefin at low cost, and is useful in the production of polymers with high functionality. There is expected.
- FIG. 1 is a flow chart showing the steps of preparing the catalyst component and polymerization catalyst of the present invention.
- novel aminosilane compounds of the present invention are compounds represented by the above-mentioned general formula (1), and such compounds include bis (ethylamino) dicyclic pentylsilane, bis (ethylamino) diisoproylsilane, Bis (methylamino) di t-peptylsilane is mentioned.
- a primary amino compound such as methylamine or ethylamine is prepared in a flask together with a solvent under an atmosphere of inert gas.
- the solvent may, for example, be a cyclic ether, a dialkyl ether, or toluene or a mixture of these.
- the solution prepared in the flask is cooled to 150 ° C. to 10 ° C., and while stirring, using a dropping funnel, under an atmosphere of inert gas, the primary amino acid is removed.
- a compound and an equimolar amount of a solution of a commercially available Glyar reagent in ether or a primary amino compound and a solution of an equimolar amount of an alkyllithium in a hydrocarbon solution are dropped into a cooled solution of the above-mentioned first class of amino compound solution.
- a dialkoxydialkylsilane compound (hereinafter referred to as DADAS compound) is dissolved in a solvent, taken as a solution in a flask with stirring under an atmosphere of inert gas, and cooled to a temperature of 50 ° C. to 10 ° C. .
- a solvent for dissolving the D A D A S compound cyclic ether, dialkyl ether, toluene and the like can be mentioned.
- the above-prepared slurry of the primary amine metal salt is dropped under an inert gas atmosphere.
- the amount of the primary amine metal salt is adjusted to be adjusted to 2 times the molar amount of the D A D A S compound.
- the temperature is gradually raised, and the reaction is carried out at a temperature of at least 40 ° C for several hours.
- the solid component formed of the metal alkoxide is separated from the solution by filtration or centrifugation under an inert gas atmosphere, the solid component is washed again, and the washing solution is added to the solution portion.
- the solvent portion of the solution portion is distilled off under an inert gas atmosphere under normal pressure or reduced pressure, and the reaction main product is purified by distillation under reduced pressure.
- the reaction solvent may be a hydrocarbon solvent such as cyclohexane, heptane, hexane or the like and a mixed solvent with the above solvent, in addition to those described above.
- the resulting aminosilane compound can be identified by a known analytical method to determine its structure.
- This aminosilane compound is a compound in which the N atom is directly bonded to the Si atom.
- 1 3 is a straight or branched aralkyl Kill group or a cycloalkyl group of from 1 to 1 2 carbon atoms, which may be identical or different
- R 4 is a hydrogen atom
- R 5 is It is a linear or branched alkyl group having 1 to 3 carbon atoms.
- the derivative of cycloalkyl is a cycloalkyl group having a substituent, specifically, alkyl substituted cyclopentyl group, alkyl substituted cyclohexyl group, alkyl substituted cycloheptyl group It can be mentioned.
- aminosilane compound represented by the above general formula (2) examples include (alkylamino) trialkylsilane, (alkylamino) dialkyl ring alkylsilane, (alkyl amino) alkyldialkyl port alkylsilane, (alkylamino) tricycloalkylsilane, (Alkylamino) (dialkylamino) dialkylsilane and (alkylamino) (dialkiamino) di-alkyl alkylsilane, bis (alkylamino) dialkylsilane, bis (alkylamino) alkyl-alkyl alkylsilane, bis (alkylamino) dialkyl-alkylsilane, bis (alkylamino) ⁇ ⁇ ⁇ ⁇ ⁇ ) (Dialkylamino) alkylsilane or bis (alkylamino) (dialkylamino) cycloalkylsilane, di (alkylamino
- bis (alkylamino) dicyclopentylsilane bis (alkylamino) diisopropylsilane, bis (alkylamino) dit-butylsilane, bis (alkylamino) t-butylethylsilane, bis (alkylamino) t-l-ptylmethylsilane, bis (alkylamino) Alkylamino) dicyclohexylsilane, bis (alkylamino) cyclohexylmethylsilane, bis (alkylamino) bis (decahydronaphthyl) silane, bis (hanolequinoleamino) cyclopentinolecyclohexanolesilane, bis (perhydroisoquinolino) (Alkylamino) alkylsilane, bis (perhydroquinolino) (alkylamino) alkylsilane, di (alkylamino
- (sec-butyl ethylamino) silane tris (methyl amino) (sec-butyl iso- propyl amino) silane, tris (ethyl amino) (methyl amino) silane, tris (ethyl amino) (n-propyl amino) silane, tris (Ethylamino) Silane, Tris (Ethylamino) (n-Peptylamino) Silane, Tris (Ethylamino) ( S ec- butylamino) Silane, Trith (Ethylamino) (T-Peptylamino) Silane, Tris (Ethylamino) ) (Neo-pentylamino) silane, tris (ethylamino) silane, tris (ethylamino) (di-iso-propylamino) silane, tris (ethylamino) (di-isobutylamino) silane, tris (e
- (Ethylamino) silane tris (dimethylamino) (n-propylamino) silane, tris (getylamino:) (n-propylamino) silane, Tris (di-n-propylamino) (n-propylamino) silane, tris (di-iso-propylamino) (n-propylamino) silane, tris (di-n_ glutamino) (n-propylamino) silane, tris (di-iso) —Peptiguanamino) (n-Propylamino) silane, Tris (t-Butylamino) (n-Propylamino) silane, Tris (Cyclopentylamino) (n-Pyroamino) Silane, Tris (Cyclohexylamino) (n-Propylamino) And the like.
- the compound represented by the above general formula (2) can be easily synthesized by a known synthesis method such as a chlorine / exchange method, a method using an organic lithium compound, a method using a Grignard reagent, or a combination thereof. It is.
- a known synthesis method such as a chlorine / exchange method, a method using an organic lithium compound, a method using a Grignard reagent, or a combination thereof.
- the aminosilane compounds of the present invention as an example of the synthesis method of bis (alkylamino) dibasic pentylsilane, dibasic pentyldi / lycoxysilane and L i salt of alkylamine of 2 times mole or M g salt of alkylamine are exemplified. It is a reaction.
- ether compounds such as THF and diethyl ether
- aromatic compounds such as toluene
- saturated hydrocarbon compounds such as pentane, hexane, heptane, and cyclohexane
- R 3 is alkylamine
- the amount of the primary amine metal salt depends on the number of alkoxy groups in the (alkoxy) ⁇ (alkyl) 4 - ⁇ silane compound, ie, ⁇ the primary amine metal salts (alkoxy) [pi (alkyl) 4 - to 1-4 times the molar amount of ⁇ silane compound may be carried out while adjusting.
- the catalyst for polymerization of olefins of the present invention is formed using the aminosilane compound represented by the above general formula (2) as an essential component.
- Preferred compounds and specific examples of the general formula (2) forming the catalyst for olefins polymerization of the present invention are the same as the description of the general formula (2) in the catalyst component for olefins polymerization.
- the solvent for polymerization of olefins of the present invention is represented by the above general formula (2)
- R 6 represents an alkyl group having 1 to 4 carbon atoms
- Q represents a hydrogen atom or a halogen atom
- p is a real number of 0 and p ⁇ 3
- the solid catalyst component (A) contains magnesium, titanium, halogen and an electron donating compound, but (a And magnesium compounds; (b) tetravalent titanium halogen compounds; and (c) electron donor compounds.
- examples of magnesium compounds include di-mo- lated magnesium, dialkylmagnesium, /, ligni-ano-le-quinole magnesium, di-olecoxy-magnesium, di- Among these magnesium compounds, dihalogenated magnesium, a mixture of dihalogenated magnesium and dialkoxymagnesium, and dialkoxy may be mentioned.
- Magnesium is preferred, and dialkoxymagnesium is particularly preferred, and specifically, dimethoxymagnesium, diethoxymagnesium, dipropoxymagnesium, dimethoxymagnesium, ethoxymethoxymagnesium, ethoxypropoxymagnesia And butoxyethoxy magnesium etc., with methoxy magnesium being particularly preferred.
- dialkoxy magnesiums may be obtained by reacting metal magnesium with an alcohol in the presence of organic metal containing hydrogen.
- the above dialkoxy danesum may be used alone or in combination of two or more. It can also be used.
- dialkoxymagnesium is granular or powdery, and the shape may be amorphous or spherical.
- dialkoxymagnesium is used, a polymer powder having a better particle shape and a narrow particle size distribution is obtained, the handling operability of the formed polymer powder at the time of the polymerization operation is improved, and the formed polymer powder is produced. This solves the problems such as filter clogging in the polymer separator due to the fine powder contained in '
- the above-mentioned spherical dialkoxymagnesium need not necessarily be truly spherical, and may be elliptical or potato-shaped. Specifically, the shape of the particles is such that the ratio (L / W) of the major axis diameter L to the minor axis diameter W is 3 or less, preferably 1 to 2, more preferably 1 to 1.5. is there.
- the average particle diameter of the above dialkoxymagnesium may be 1 to 200 ⁇ . Preferably, it is 5 to 150 ⁇ . In the case of spherical dialkoxy magnesium, the average particle size is 1 to 100 / ⁇ , preferably 5 to 50 ⁇ m, and more preferably 10 to 40 ⁇ .
- the particle size it is preferable to use one having less fine powder and coarse powder and having a narrow particle size distribution. Specifically, particles of 5 / m or less are 20% or less, preferably 10% or less. On the other hand, particles of 100 ⁇ or more are 10% or less, preferably 5% or less. Further, the particle size distribution is expressed by D 90 / D 10 (where, D 90 is a particle size at 90% in cumulative particle size, and D 10 is a particle size at 10% in cumulative particle size). It is 3 or less, preferably 2 or less.
- the method for producing the spherical dialkoxymagnesium as described above is disclosed, for example, in Japanese Patent Application Laid-Open No. 5 8 4 12 3, JP-A 6 2 5 6 3 3, and Japanese Patent Application Laid-Open No. 3-74 34 1 Japanese Patent Laid-Open Publication No. Hei 4 3 6 8 3 9 1 Japanese Patent Laid-Open Publication No. Hei 8-7 3 No. 3 88.
- component (b) used for the preparation of the component (A) in the present invention has a general formula
- R 7 represents an alkyl group having 1 to 4 carbon atoms
- X represents a halogen atom
- n is an integer of 0 ⁇ n ⁇ 4
- titanium tetrahalides such as titanium tetrachloride, titanium tetrabromide, titanium tetraiodide, etc. as titanium halides, mettitanium trichloride as alkoxytitanium halides, methoxytitanium trichloride, etc.
- titanium tetrahalides such as titanium tetrachloride, titanium tetrabromide, titanium tetraiodide, etc.
- titanium halides mettitanium trichloride as alkoxytitanium halides, methoxytitanium trichloride, etc.
- Propoxy titanium trichloride, n-butoxy titanium trichloride, dimethyl titanium titanium dioxide, diethyl titanium titanium dioxide, dipropoxy titanium dichloride, di-n-butoxy titanium dioxide Examples thereof include trimethytitanium chloride, triethoxytitanium chloride, tripropoxytitanium chloride,
- the electron-donating compound (hereinafter sometimes simply referred to as “component (c)”) used in the preparation of the solid catalyst component (A) in the present invention is an organic compound containing an oxygen atom or a nitrogen atom.
- component (c) used in the preparation of the solid catalyst component (A) in the present invention is an organic compound containing an oxygen atom or a nitrogen atom.
- component (c) for example, alcohols, phenols, ethers, esters, ketones, acid halides, aldehydes, amines, amines, amides, nitriles, isocyanates, Si 1 0
- Organic silicon compounds containing _C bond or Si—N—C bond are listed.
- alcohols such as methanol, ethanol, n-propanol, 2-ethylhexanol, phenols such as phenol and cresol, dimethyl ether, getinole ether, dipropyl ether, dibutynore atenole , Diamino no etenore, diphenino lea tenore, 9, 9 bis (methyoxymethyl) fluorene, 2-isopropyl bis 2-isobenzyl, 1, 3-ethers such as 3-dimethyl propane, methyl formate, acetic acid Ethyl acetate, propyl acetate, propyl acetate, octyl acetate, cyclohexethyl acetate, ethyl propionate, ethyl butyrate, ethyl benzoate, benzoate pill, putyl benzoate, otatyl benzoate, octyl acetate hexy
- Silicon compounds bis (alkyl Ruamino) Dialkoxysilane, bis (sic alkylamino) dialkoxysilane, alkyl (alkylamino) dialkoxysilane, dialkylamino trialkoxysilane, sicmouth alkylamino trialkoxysilane, etc.
- the organic silicon compound to contain can be mentioned.
- esters, particularly aromatic dicarboxylic acid diesters are preferably used, and phthalic acid diesters and phthalic acid diester derivatives are particularly preferable.
- phthalates include dimethyl phthalate, jetyl phthalate, di-n-propyl phthalate, di-isopropinoleate phthalate, di-n-butyrene phthalate, di-isobutyl phthalate, isobutyl methyl phthalate, phthalate Acid methyl isopyrol pylic acid, ethyl phthalate (n-propinole), phthalic acid ethyl (n-butyl), phthalic acid ethyl (isobutyl), phthalic acid di-n-pentyl, phthalic acid diisopentyl phthalate, dineopentyl phthalate, phthalic acid Dihexyl, Phthalate di-n-Hepteole, Phthalate di-n-Octyl / Le, Phthalate bis (2, 2-dimethylhexyl), Phthalate bis (2-ethylhexyl), Phthalate di-
- one or two hydrogen atoms of the benzene ring to which two ester groups of the above phthalic acid diester are bonded is an alkyl group having 1 to 5 carbon atoms, or a chlorine atom, a bromine atom or the like. What is substituted by halogen atoms, such as a fluorine atom, is mentioned.
- the solid catalyst component prepared using the phthalic acid ester derivative as the electron donor compound can further improve the hydrogen flow to a greater effect on the melt flow rate, that is, the hydrogen response can be further improved. The same amount or a small amount can improve the melt flow rate of the polymer.
- 4-bromophthalenoic acid dineopentinole 4-bromophthalic acid It is also preferable to use two or more of the above-mentioned esters in combination, and the total carbon number of the alkyl groups of the esters used in that case is compared with that of the other esters. When the difference is 4 or more, it is desirable to combine the esters. .
- the aminosilane compound represented by the general formula (2) can also be used as the electron donor compound (c) (internal donor) of the solid catalyst component (A).
- Preferred compounds and specific examples of the aminosilane compound represented by the general formula (2) used as an internal donor are the same as those described in the general formula (2) in the catalyst component for polymerization of olefins.
- the above (a), (b), and (c) are brought into contact in the presence of the hydrocarbon compound (d) (hereinafter sometimes simply referred to as "component (d)").
- component (d) the hydrocarbon compound (d)
- the preferred embodiment is a method of preparing the component (A) by the following method. Specifically, as the component (d), the boiling point of toluene, xylene, ethyl benzene, diethyl hexene, hexene hexene, etc. is 50 Hydrocarbon compounds at a temperature of 150 ° C. are preferably used. These may be used alone or in combination of two or more.
- a suspension is formed from the component (a), the component (c) and the hydrocarbon compound (d) having a boiling point of 50 to 150 e C. And the suspension formed from the component (b) and the component (d) '
- a preparation method can be mentioned by contacting with a solution and then reacting.
- polysiloxane (hereinafter sometimes simply referred to as "component (e)"), and to use a polysiloxane.
- component (e) a polysiloxane
- Polysiloxane is a polymer having a siloxane bond (one S i -O bond) in the main chain, but is also generically called silicone oil, and its viscosity at 25 ° C. is 0.02 to 10 cm 2 / s. It is a liquid or viscous chain-like, partially hydrogenated, cyclic or modified polysiloxane having a temperature of 2 to 1000 centistokes.
- linear polysiloxane dimethylpolysiloxane and methylphenylpolysiloxane
- partially hydrogenated polysiloxane methylhydogenpolysiloxane having a hydrogenation rate of 10 to 80%
- cyclic polysiloxane Hexamethylsecto trisiloxane, otatamethylcyclotetrasiloxane, decamethylsectopentanesiloxane, 2,4,6-trimethylsuccinic trisiloxane, 2,4,6,8-tetramethylcyclotetrasiloxane, and as modified polysiloxanes
- modified polysiloxanes examples thereof include higher aliphatic acid group-substituted dimethylsiloxane, epoxy group-substituted dimethylsiloxane, and polyoxyalkylene group-substituted dimethylsiloxane.
- decamethylcyclopentasiloxane and dimethylpolysiloxane are preferable, and decamethylcyclopentasiloxane is particularly preferable.
- the above components (a), (b) and (c), and if necessary, the component (d) or the component (e) are brought into contact to form the component (A).
- the preparation method of component (A) is described.
- the mug Nesium compound (a) is suspended in alcohol, halogen hydrocarbon solvent, tetravalent titanium halogen compound (b) or hydrocarbon compound (d), and electron donor compound (c) such as phthalic acid diester and Z Or a method of obtaining component (A) by contacting tetravalent titanium halogen compound (b).
- a spherical magnesium compound by using a spherical magnesium compound, it is possible to obtain a component (A) which is spherical and has a sharp particle size distribution, and without using a spherical magnesium compound, for example, a solution or By forming particles by spraying and drying the suspension by the so-called Spray-dry method, it is possible to obtain a component (A) which is similarly spherical and has a sharp particle size distribution.
- the contact of each component is carried out while stirring in a container equipped with a stirrer under an inert gas atmosphere and under the condition where water and the like are removed.
- the contact temperature is the temperature at the time of contact of each component at the time of contact of each component, and may be the same temperature as the reaction temperature or a different temperature.
- the contact temperature may be a relatively low temperature range around room temperature when simply contacting and stirring and mixing, or dispersing or suspending and modifying it, but the reaction may be carried out after contact and the product
- the temperature range of 40 ° to 130 ° C. is preferred.
- reaction temperature is less than 40 ° C., the reaction does not proceed sufficiently, resulting in insufficient performance of the prepared solid catalyst component, and if it exceeds 130 ° C., evaporation of the used solvent is caused. Becomes prominent, and it becomes difficult to control the reaction.
- the reaction time is 1 minute or more, preferably 10 minutes or more, and more preferably 30 minutes or more.
- the component (a) is suspended in the component (d), then the component (b) is brought into contact and then the component (c) and the component (d) are brought into contact.
- a method of preparing the component (A) by reaction, or suspending the component (a) in the component (d) and then bringing the component (c) into contact, followed by contacting the component (b), the reaction Component (A) by Methods of preparing can be mentioned. Also the ingredients thus prepared
- the performance of the final solid catalyst component can be improved by contacting component (b), or component (b) and component (c) with (A) again or multiple times. At this time, it is desirable to carry out in the presence of the hydrocarbon compound (d).
- a suspension is formed from the component (a), the component (c) and the hydrocarbon compound (d) having a boiling point of 50 to 150 ° C. And the component (d) is brought into contact with the suspension and then reacted to give a preparation method.
- component (A) in the present invention As a preferable preparation method of component (A) in the present invention, the following methods can be mentioned.
- a suspension is formed from the component (a), the component (c) and the hydrocarbon hydride compound (d) having a boiling point of 50 to 150 ° C.
- a mixed solution is formed from the component (c) and the hydrocarbon hydride compound (d) having a boiling point of 50 to 150 ° C., and the above suspension is added to the mixed solution. Thereafter, the temperature of the resulting mixed solution is raised for reaction treatment (first reaction treatment). After completion of the reaction, the obtained solid substance is washed with a liquid hydrocarbon compound at room temperature, and the solid substance after washing is used as a solid product.
- dialkoxymagnesium (a) is suspended in a hydrocarbon compound (d) having a boiling point of 50 to 150 ° C.
- the suspension is brought into contact with a tetravalent titanium halogen compound (b) and then subjected to a reaction treatment.
- a reaction treatment Before or after bringing the turbid solution into contact with the tetravalent titanium halogen compound (b), one or two or more kinds of the electron donor compound (c) such as phthalic acid diester, etc.
- the reaction is carried out by bringing the component (e) into contact, if necessary, by contacting at ° C. to obtain a solid product (1).
- the solid product (1) is washed with a liquid hydrocarbon compound at room temperature (intermediate washing), and then the tetravalent titanium halide (b) is again added to the solid product in the presence of the hydrocarbon compound.
- the reaction is carried out by contacting in ° C to obtain a solid product (2). If necessary, the intermediate washing and reaction may be repeated several more times.
- the solid product (2) is decanted and washed with a liquid hydrocarbon compound at room temperature to obtain a solid catalyst component (A).
- the ratio of the amount of each component used in preparation of the solid catalyst component (A) can not be generally determined because it varies depending on the preparation method, but for example, a tetravalent titanium halide compound (1 mole of magnesium compound (a) b) power SO. 5 to 100 mol, preferably 0.5 to 50 mol, more preferably 1 to 10 mol, and the electron donor compound (c) is 0.1 to 10 mol, The amount is preferably 0.1 to 1 mole, more preferably 0.2 to 0.2 mole, and the hydrocarbon compound (d) force SO.
- the molar ratio of the polysiloxane (e) is from 0.01 to 1: 100 g, preferably from 0.5 to 80 g, more preferably from 1 to 100 mol. 50 g.
- the content of titanium, magnesium, halogen atoms, and electron donor compounds in the solid catalyst component (A) in the present invention is not particularly limited, but preferably 0.5 to 8 wt% of titanium, preferably 1.0 to 8.0 by weight 0/0, more preferably from 2.0 to 8.0 weight 0/0 magnesium 1 0-7 0 %, More preferably 10 to 50% by weight, particularly preferably 15 to 40% by weight, still more preferably 15 to 25% by weight, 20 to 90% by weight of halogen atoms, more preferably 30 to 50% by weight 85% by weight, particularly preferably 4 ° to 80% by weight, and still more preferably 45 to 75% by weight, and the total amount of electron donating compounds is 0.5 to 30% by weight, more preferably a total of 1 to 25 % By weight, particularly preferably a total of 2 to 20% by weight.
- the organic aluminum compound (B) (hereinafter sometimes simply referred to as “component (B)”) used to form the catalyst for olefin polymerization of the present invention is represented by the above general formula (3)
- the compound is not particularly limited as long as it is a compound, but R 6 is preferably a ethyl group or isoptyl group, Q is preferably a hydrogen atom, a chlorine atom or a bromine atom, and p is preferably 2 or 3. Is particularly preferred.
- Specific examples of such organic aluminum compounds (B) include triethyl aluminum, jetyl aluminum hydroxide, triisopropyl alcohol, jetyl aluminum bromide and jet aluminum aluminum hydride 1 Species or two or more species can be used.
- triethylaluminum and triisobutylaluminum are used.
- an aminosilane compound represented by the above general formula (2) is there.
- Preferred compounds and specific examples of the general formula (2) used as the component (C) are the same as those described for the general formula (2) in the catalyst component for olefins polymerization.
- an organic silicon compound other than the above-mentioned aminosilane compound hereinafter may be simply referred to as “component (D)
- component (D) an organic silicon compound other than the above-mentioned aminosilane compound
- an organic silicon compound (D) As such an organic silicon compound (D), the following general formula 'R 8 q S i (OR 9 ) 4 q (wherein, R 8 is hydrogen) Or an alkyl group having 1 to 20 carbon atoms, an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group, a phenyl group, a bulyl group, an aryl group, an aryl group, an alkylamino group, a cycloalkylamino group, and a polycyclic amino group, and may be the same or different.
- R 9 represents a linear or branched alkyl group having 1 to 20 carbon atoms, a cycloalkyl group, a vinyl group, a aryl group, or a aralkyl group, which may be the same or different, and q is an integer of 1 to 3 It is. It is 1 type, or 2 or more types of organic key compounds represented by 2.).
- organic silicon compound (D) examples include di-n-propyldimethoxysilane, diisopropyldimethoxysilane, di-n-butyldimethoxysilane, di-n-butyl jetoxysilane, t-butyl ester.
- olefins include ethylene, propylene, 1-butene, 1-pentene, 4-methyl- 11-pentene, vinyl chloride hexene and the like, and these olefins can be used alone or in combination of two or more.
- ethylene, propylene and 1-butene are preferably used.
- propylene is particularly preferred.
- copolymerization with other olefins can be carried out.
- the olefin to be copolymerized is ethylene, 1-butene, 1-pentene, 4-methinole 1-pentene, bininolecyclohexane, etc. These olefins can be used alone or in combination of two or more. Among these, ethylene and 1-butene are preferably used.
- copolymerization of propylene and other olefins random copolymerization in which propylene and a small amount of ethylene are polymerized in one step as a comonomer, and the first step
- a so-called propylene-ethylene block in which propylene is homopolymerized in a first polymerization tank, and propylene and ethylene are copolymerized in a second stage (second polymerization tank) or multiple stages (multistage polymerization tank). Copolymerization is representative. Also in such random copolymerization and block copolymerization, the above components
- the catalyst of the present invention comprising (A), component (B) and component (C) is effective and not only good in catalytic activity, stereoregularity and Z or hydrogen response, but also copolymerization characteristics and properties. The properties of the copolymer are also good.
- the above-mentioned component (D) may be mixed and used, or the component (C) and the component (D) may be separately used in a multistage polymerization tank of block copolymerization. It can also be done.
- known electron donor compounds such as alcohols, oxygen gas or ketone are polymerized.
- the alcohol include ethyl alcohol, isopropyl alcohol and the like, and the amount used is 0.01 to 10 mol, preferably 0.1 to 2 mol, per 1 mol of the component (B).
- each component is optional as long as it does not affect the effects of the present invention, and is not particularly limited.
- the component (B) is usually a titanium atom in the component (A). Hit,:! It is used in the range of 200 to 200 mol, preferably 50 to 1 000 mol.
- Component (C) is used in the range of 0.000 to 10 mol, preferably 0.01 to 2 mol, particularly preferably 0.:! To 0.5 mol, per 1 mol of component (B).
- component (D) is used in combination, the content per mole of component (B) is from 0.000 to 2:10 mol, preferably from 0.1 to 2 mol, particularly preferably from 0.1 to 0.5 mol. Or 0.1 to 10 moles, preferably 0.0 :!
- each component is a compound (B) is charged into the polymerization system, and then the force of bringing the aminosilane compound (C) into contact, the component (C) and the component (C) mixed beforehand D) Force to contact D) Alternatively, the component (C) and the component (D) are brought into contact in any order to obtain the solid catalyst component (A). It is desirable to make contact.
- the organic aluminum compound (B) is first charged into the polymerization system, while the component (A) is brought into contact with the component (C) or the component (C) and the component (D) in advance, and the components are brought into contact with each other. It is also a preferred embodiment to charge (A), component (C) or component (C) and component (D) into the polymerization system and form a catalyst to form a catalyst.
- the hydrogen response of the catalyst and the crystallinity of the produced polymer are further improved by previously treating the component (A) with the component (B) or the component (C) and the component (D).
- the polymerization method in the present invention can be carried out in the presence or absence of an organic solvent, and olefin monomers such as propylene can be used for polymerization in any state of gas and liquid.
- the polymerization temperature is 200 ° C. or less, preferably 150 ° C. or less
- the polymerization pressure is 1 OMP a or less, preferably 6 MP a or less.
- both continuous polymerization method and batch polymerization method are possible.
- the polymerization reaction may be carried out in one stage, or may be carried out in two or more stages.
- the polymerization of olefin using the catalyst formed from the component (A), the component (B) and the component (C) in the present invention also referred to as "main polymerization"
- monomers similar to the main polymerization such as olefins or styrene, can be used.
- the component (A), the component (B) and the component Z or the component (C) are brought into contact with each other in the presence of olefins, and per 1 g of the component (A):!
- component (B) and / or the component (C) are further brought into contact to form a catalyst.
- component (D) is used in combination, component (A), component (B) and component (D) are brought into contact with each other in the presence of orephins during the prepolymerization, and component (C) is used in the main polymerization. You can also.
- the contact sequence of each component and the monomer is optional, it is preferable to first load the component (B) in the prepolymerization system set to an inert gas atmosphere or a gas atmosphere for polymerization such as propylene.
- olefin such as propylene and / or one or more other olefins make contact.
- the prepolymerization temperature is optional and is not particularly limited, but is preferably in the range of 10 ° C to 70 ° C, more preferably in the range of 15 ° C to 50 ° C.
- the organic silicon compound of the present invention can also be used as a conductor insulating film material, a surface treatment agent such as a printed wiring base material, a photoresist material, or an intermediate material thereof.
- a THF solution of ethylamine is separated into a flask fully purged with nitrogen gas under a nitrogen stream, cooled to a temperature of 10 ° C. to 0 ° C., and stirred, using a dropping funnel to obtain a commercial solution.
- the hexane solution of butyllithium was gradually added dropwise equimolar to ethylamine. After the end of commerce, gradually raise the temperature, The mixture was reacted at 50 ° C. for 2 hours to prepare a lithium salt slurry of ethylamine. Then, take it into a flask that has been fully purged with nitrogen gas.
- a THF solution of ethylamine is separated into a flask fully purged with nitrogen gas, cooled to a temperature of 10 ° C. to 0 ° C., and while stirring, using a dropping funnel, a commercially available butyllithium solution is obtained.
- the hexane solution was equimolar to ethylamine and gradually added dropwise. After completion of the dropwise addition, the temperature was gradually raised, and reaction was carried out at 50 ° C. for 2 hours to prepare a lithium salt slurry of acetylamine.
- Dicyclohexyl dimethic acid instead of t-peptyl dimethyxsilane
- a bis (methylamino) dicyclohexylsilane was obtained by the same method as in Example 2 except that a silane was used.
- the result is 66. 03% (66. 0 7%), H is 1 1. 86% (1 1. 88%), and N is 1 1. 00% (1 1. 0 1%). (The numbers in parentheses are theoretical quantities). +.
- the compound was synthesized in the same manner as in Example 2 except that t-butylethyldimethoxysilane was used instead of t-butylethyldimethoxysilane and bis (methylamino) cyclohexylmethylsilane was obtained.
- the elemental analysis result C 57. 9 1% (58. 00%), H was 1 1. 68% (1 1. 9 0%), N was 1 5. 00% (1 5. 03%) (numbers in parentheses) Is a theoretical quantity).
- the reaction mixture was filtered, and the amount of Dalynia reagent produced in the resulting ether solution was determined by acid-algorithm titration. As a result, the yield was 20%, and the concentration was 0.04 mol Z 100 m 1.
- a flask sufficiently purged with nitrogen add 5 Oml of a toluene solution containing 0.02 mol of tetramethoxysilane, and cool to 100 ° C while stirring.
- one reagent having a decahydonaphthyl group synthesized above was added dropwise. After completion of the addition, the temperature was gradually raised and reacted at 80 ° C. for 2 hours.
- Ethylamine is used in place of methylamine and t-butylethyldimethoxysilane is used in place of pentyldimethoxysilane.
- the compound was synthesized in the same manner as in Example 2 except that used, to obtain bis (ethyamino) cyclohexylcyclopentylsilane. Elemental analysis result, C 6
- a round-bottomed flask equipped with a stirrer and having a volume of 2000 ml and sufficiently replaced with nitrogen gas was charged with 150 g of methoxymagnesium and 50 ml of toluene and suspended.
- the suspension is then pre-charged in a round bottom flask, equipped with a stirrer and fully purged with nitrogen gas, in a round bottom flask with a volume of 200 ml and titanium tetrachloride 300 m. It was added to the solution of 1.
- the suspension was then allowed to react at 5 ° C. for 1 hour. Thereafter, 2.5 ml of 1 n-butyl phthalate was added, and the mixture was heated to 100 ° C., and then reacted for 2 hours while stirring. After the reaction, the product
- the catalyst activity indicating the amount (F) of polymer produced per hour of polymerization time per 1 g of the solid catalyst component was calculated by the following equation.
- Catalyst activity product polymer (F) gZ solid catalyst component gZl time
- H I (H) g / (G) g X 1 0 0
- MI melt index
- the molecular weight distribution of the polymer was determined by measurement using a cross-fractionation chromatograph (CFC) (CFCT-150 B, manufactured by Mitsubishi Chemical Corporation) under the following conditions.
- CFC cross-fractionation chromatograph
- Measuring range 0 ° C to 1 40 ° C
- Example 9 The experiment was carried out in the same manner as in Example 9 except that the bis (methylamino) t-butylethylsilane obtained in Example 2 was used instead of di-bis (ethylamino) dicyclopentylsilane. It is shown in Table 4.
- Example 4 The experiment was conducted in the same manner as in Example 9 except that the bis (methylamino) t-butylmethylsilane obtained in Example 4 was used instead of bis (ethylamino) dipentyl port pentylsilane. The obtained results are shown in Table 4.
- Example 9 The experiment was performed in the same manner as in Example 9 except that the bis (methylamino) dicyclohexylsilane obtained in Example 5 was used instead of the bis (ethylamino) dicyclopentylsilane. Also, the molecular weight distribution of the polymer was measured. The obtained results are shown in Table 4.
- Example 9 The experiment was carried out in the same manner as in Example 9 except that the bis (methylamino) cyclic hexylmethylsilane obtained in Example 6 was used instead of bis (ethylamino) dicyclopentylsilane. The obtained results are shown in Table 4.
- Example 7 Obtained in Example 7 in place of bis (ethylamino) dicyclopentylsilane
- the experiment was carried out in the same manner as in Example 9 except for using bis (methylamino) bis (decahydonaphthyl) silane.
- the obtained results are shown in Table 4.
- Example 9 The experiment was conducted in the same manner as in Example 9 except that the bis (ethinoleamino) cyclohexylenocyclopentisilane obtained in Example 8 was used instead of bis (ethylamino) dicyclopentylsilane.
- the obtained results are shown in Table 4. '
- a round-bottomed flask equipped with a stirrer and fully purged with nitrogen and having a volume of 5 O Oml is charged with 4.76 g of anhydrous magnesium chloride, 25 ml of decane and 23.4 ml of 2-ethylhexyl alcohol. The mixture was allowed to react at 130.degree. C. for 2 hours to give a homogeneous solution. Then, 1.1 g of phthalic anhydride was added to the homogeneous solution and reacted at 130 ° C. for 1 hour. The solution is then loaded into a 500 ml round bottom flask, equipped with a stirrer and fully purged with nitrogen gas, and in 200 ml of titanium tetrachloride kept at 120.degree.
- the whole amount was dropped over 1 hour.
- the mixed solution was heated to 110 ° C. for 4 hours, and then 2.68 ml of diisobutyl phthalate was added and allowed to react for 2 hours.
- the liquid portion is removed by filtration, and the remaining solid component is washed with decane and hexane at 11.degree. C. until no free titanium compound is detected, filtered and dried to give a powdery solid.
- the catalyst component was obtained.
- the titanium content in this solid catalyst component was measured to be 3.1% by weight.
- a polymerization catalyst was formed and polymerized in the same manner as in Example 9 except that the solid catalyst component obtained above was used. The obtained results are shown in Table 4.
- a solid catalyst component is prepared and polymerized in the same manner as in Example 9 except that a polymerization catalyst is formed and polymerized using tris (methylamino) t-butylsilane instead of bis (ethylamino) dicyclopentanolesilane. Catalyst formation and polymerization were carried out. The results are shown in Table 5.
- a solid catalyst component was prepared in the same manner as in Example 9, except that formation of a polymerization catalyst and polymerization were carried out using bis (methylamino) di t-butylsilane instead of bis (ethylamino) dicyclopentylsilane. Catalyst formation and polymerization were carried out. The results are shown in Table 5.
- a solid catalyst component was prepared in the same manner as in Example 9 except that the formation and polymerization of a polymerization catalyst were carried out using bis (methylamino) dihydroxy pentylsilane instead of bis (ethinoleamino) dicyclopentinolesilane. Preparation and formation of a polymerization catalyst and polymerization were carried out. The results are shown in Table 5.
- a solid catalyst component was prepared in the same manner as in Example 9 except that a polymerization catalyst was formed and polymerized using bis (ethylamino) t-butylisotylsilane instead of bis (ethylamino) dicyclopentylsilane. And the formation and polymerization of a polymerization catalyst. The results are shown in Table 5.
- a solid was prepared in the same manner as in Example 9, except that the formation of a polymerization catalyst and polymerization were carried out using bis (methylamino) di-4-methyoxyphenylsilane instead of bis (ethinoleamino) dicyclopentinolesilane.
- a catalyst component was prepared, and formation and polymerization of a polymerization catalyst were carried out. The results are shown in Table 5.
- a solid catalyst component was prepared in the same manner as in Example 9 except that formation of a polymerization catalyst and polymerization were carried out using bis (methylamino) texylmethylsilane instead of bis (ethinoleamino) dicyclopentysilane. Catalyst formation and polymerization were carried out. The results are shown in Table 5.
- a solid catalyst component was prepared in the same manner as in Example 9, except that formation of a polymerization catalyst and polymerization were carried out using bis (methylamino) didecahydonaphthylsilane instead of bis (ethylamino) dipentyl port pentylsilane. Formation of polymerization catalyst and polymerization were carried out. The results are shown in Table 5.
- a solid catalyst component was prepared in the same manner as in Example 9 except that formation of a polymerization catalyst and polymerization were carried out using tris (methylamino) cyclohexylsilane instead of bis (ethylamino) dicyclopentylsilane. Catalytic Formation and polymerization were performed. The results are shown in Table 5.
- a solid catalyst component was prepared and polymerized in the same manner as in Example 9 except that formation of a polymerization catalyst and polymerization were carried out using bis (getyamino) dimethyxsilane in place of bis (ethino reamino). Catalyst formation and polymerization. The obtained results are shown in Table 4.
- a solid catalyst component was prepared in the same manner as in Example 9 except that formation of a polymerization catalyst and polymerization were carried out using diisopropyl aminotriethoxysilane instead of bis (ethinoleamino) dicyclopentinolesilane, and a catalyst for polymerization was prepared. Formation and polymerization. The obtained results are shown in Table 4.
- a solid catalyst component was prepared in the same manner as in Example 9, except that tris (dimethylamino) methoxysilane was used instead of bis (ethylamino) dipentyl port pentylsilane to form a polymerization catalyst and carry out polymerization, The formation and polymerization of a polymerization catalyst were carried out. The obtained results are shown in Table 4.
- a solid catalyst component was prepared in the same manner as in Example 9 except that cyclohexylmethyldimethoxysilane was used instead of bis (ethinoleamino) dicyclopentylsilane, and the polymerization time was 1 hour and 2 hours, and a polymerization catalyst was used. Formation and polymerization were performed. The obtained results are shown in Table 4. (Example 2 9)
- a solid catalyst component was prepared in the same manner as in Example 9 except that bis (methylamino) dicyclopentylsilane synthesized in Example 2 was used instead of bis (ethylamino) dicyclopentylsilane, and a polymerization catalyst was prepared. Formation and polymerization were performed. The results obtained are shown in Table 4.
- the resulting toluene solution is concentrated under reduced pressure at 50 ° C. to a volume of about 1 ⁇ 4 and then 150 ml of dehydrated and deoxygenated n-heptane are added, 10 ° The mixture was cooled to C and left to stand overnight for recrystallization. The precipitated needle crystals were separated by filtration and dried under a nitrogen gas atmosphere to obtain tetrakis (methylamino) silane. From the weight of crystals, the yield in one recrystallization was 50%. A second recrystallization was carried out from the residue, and the obtained crystals added up to a yield of 55%.
- the products were identified from elemental analysis of C, H and N. As a result, it was 32. 23% (32. 40%), H was 106. 7% (10. 88%), and N was 37. 70% (37. 78%). The numbers in parentheses are theoretical quantities).
- a solution of 50 ml of a toluene solution containing 0.2 mol of t-butylamine was collected into a flask sufficiently purged with nitrogen gas, and cooled to 1 ° C. with stirring.
- a 60 ml THF solution containing 0.2 mol of BuMg C 1 was slowly dropped using a dropping funnel. After the addition was completed, the temperature was gradually raised and reacted at 40 ° C. for 2 hours to complete.
- 5 Om 1 of a toluene solution containing 0.1 mol of tetramethoxysilane was collected in a flask purged thoroughly with nitrogen gas, and cooled to 1 ° C. with stirring.
- a solution of 50 ml of a toluene solution containing 0.1 mol of ethylamine was collected into a flask sufficiently purged with nitrogen gas, and cooled to 1 ° C. with stirring.
- To this cooled solution was slowly added dropwise using a dropping funnel a 600 ml solution of T HF containing 0.1 mol of BuMg C 1. After completion of the dropwise addition, the temperature was gradually raised and reacted at 20 ° C. for 2 hours to complete.
- 5 Oml of a toluene solution containing 0.5 mol of bis (t-butylamino) dimethysilane was collected into a flask sufficiently purged with nitrogen gas, and cooled to -10 ° C under stirring. .
- the slurry of the mixture of Mg salts of ethylamine obtained in the above reaction was gradually added to a toluene solution containing bis (t-butylamino) dimethysilane with a dropping funnel. After completion of the addition, the reaction was completed at 50 ° C. for 4 hours.
- the solid produced by the reaction was centrifuged under a stream of nitrogen. Furthermore. The solid is washed twice with 2 '0 ml of toluene and added to the solution Eh. The solvent was distilled off from the solution under reduced pressure, and the solution was concentrated and then heated under reduced pressure to refine the 3 ⁇ 4 product bis (t-peptylamino) bis (gety lamino) silane by distillation.
- the solid produced by the reaction was centrifuged under a stream of nitrogen. Further, the solid was washed twice with 2 Om 1 of toluene and added to the solution. The solvent was distilled off from the solution under reduced pressure, and the solution was concentrated and then heated under reduced pressure to distill and purify the main product bis (perhydroquinolino) bis (ethylamino) silane.
- the products were identified from elemental analysis of C, H and N. as a result, . Is 6 7. 20% (6 7. 2 9%), H is 1 1. 30% (1 1. 2 9%), N is 1 4. 2 5% (1 4. 2 7%) (The numbers in parentheses are theoretical quantities).
- Toluene solution containing 0.5 mol of di-t-butylamine 80 m 1 Take a three-necked flask purged thoroughly with nitrogen gas under a stream of nitrogen, and stir for 10 minutes. It cooled to C. 50 ml of a THF solution containing 0.5 mol of BuMg C 1 are slowly dropped into the toluene solution containing dit-peptylamine described above using a dropping funnel. After completion of the dropwise addition, the temperature was raised to react at 40 ° C. for 2 hours. In this way, a slurry of M g salt of di-t-peptylamine was obtained.
- Example 36 A synthesis procedure similar to that of Example 36 was used to obtain 0.1 N Mg-containing slurry of di-t-peptylamine. Next, a 50 ml of toluene solution containing 0.50 moles of tetramethoxysilane is separated into three flasks sufficiently purged with nitrogen gas under a stream of nitrogen and cooled to 10 ° C. with stirring. did. Next, 100 ml of a slurry of the above M g salt of 0.1 g of dit-butynoamine is gradually added dropwise to the toluene solution using a dropping funnel. After completion of the addition, the reaction was carried out at 60.degree. C. for 4 hours.
- a toluene solution containing 0.04 mol of bis (di t-butylamino) dimethysilane is thoroughly purged with nitrogen gas into a three-necked flask under a nitrogen stream, and cooled to 1 o ° c with stirring. did.
- 80 m 1 of the above slurry of 0.8 g of M g salt of methylamine is gradually dropped using a dropping funnel. After completion of the dropwise addition, the temperature was gradually raised and reacted at 70 ° C. for 5 hours. After completion of the reaction, the solid was separated by centrifugation under a nitrogen stream. The solid was further washed twice with 20 ml of toluene and added to the solution portion.
- the Mg salt slurry of t-butyl ethyl amine thus obtained was used as a toluene solution of tetrakis (methylamino) silane obtained according to the method of Example 3 (0.5 mol / 50 ml) 50 m l was separated and dropped into flasks cooled to 10 ° C. After completion of the dropwise addition, the reaction was carried out at 50 ° C. for 2 hours. The resulting reaction mixture was concentrated to about 1/2 volume at room temperature under reduced pressure, and then centrifuged under a stream of nitrogen to separate solid and liquid. Similarly, the solid was washed twice with 15 ml of toluene.
- Example 44 The experiment was carried out in the same manner as in Example 9 except that the tetrakis (methylamino) silane obtained in Example 3 was replaced with bis (ethylamino) dicyclopentylsilane. The obtained results are shown in Table 6. (Example 44)
- Example 43 The same procedure as in Example 43 was carried out except that the amount of hydrogen gas was changed to 4 liters and the amount was changed to 1 liter in the formation of the polymerization catalyst and the polymerization. The obtained results are shown in Table 6.
- Example 9 except that bis (t-butylamino) bis (getilamino) silane 0.13 mm o 1 obtained in Example 34 was used instead of bis (ethylamino) dipentyl port pentylsilane 0-26 mm o 1 The same experiment was conducted. The obtained results are shown in Table 6.
- the bis (perhydroquino lino) bis (gethylamino) silane obtained in Example 3 was used in place of bis (ethylamino) dicyclyl opening penzolesilane 0-26 mm 0 1 except that 0.13 mm 0 1 was used.
- the experiment was performed in the same manner as in Example 9. The obtained results are shown in Table 6.
- Example 9 except that tris (ethylamino) di t-butylaminosilane 0.13 mm o 1 obtained in Example 3 6 was used instead of bis (ethylamino) dipentyl port pentylsilane 0-26 mm o 1 The experiment was performed in the same manner as The obtained results are shown in Table 6.
- Example 6 except using bis (di t-butylamino) bis (methylamino) silane 0.13 mm o 1 obtained in Example 3 7 instead of bis (ethylamino) dicyclopentylsilane 0.26 mm ol The experiment was conducted in the same manner as in 9. The obtained results are shown in Table 6.
- Example 9 is the same as Example 9 except using the tris (ethylamino) (getilamino) silane 0.13 mmo 1 obtained in Example 3 9 in place of bis (ethinoleamino) dicyclic mouthpiece / lesylan 0.26 mmo 1. The experiment was performed similarly. The obtained results are shown in Table 6.
- Example 7 was repeated except that bis (ethyamino) bis (getilamino) silane obtained in Example 40 was used instead of 0.26 mmol of bis (ethynoreamino) dicyclopentinolesilane. The experiment was conducted similarly. The obtained results are shown in Table 6.
- Example 6 The experiment was conducted in the same manner as in Example 9 except that the tris (methylamino) (t-butylethyamino) silane obtained in Example 41 was used in place of bis (ethylamino) dicyclopentylsilane. The obtained results are shown in Table 6.
- Example 5 The experiment was conducted in the same manner as in Example 9 except that the tris (methylamino) diiso-propylaminosilane obtained in Example 42 was used instead of bis (ethylamino) dicyclopentylsilane. The obtained results are shown in Table 6. (Example 5 4)
- Example 5 5 The experiment was conducted in the same manner as in Example 17 except that the tetrakis (methylamino) silane obtained in Example 33 was used in place of bis (ethylamino) dicyclopentylsilane. The obtained results are shown in Table 6. (Example 5 5)
- Example 6 The experiment was carried out in the same manner as in Example 18 except that the tetrakis (methylamino) silane obtained in Example 3 was used instead of bis (ethylamino) dipentyl port pentylsilane. The obtained results are shown in Table 6.
- Example 6 1 The polymerization of propylene under the same conditions was carried out under the same conditions as in Example 9, except that tris (ethyamino) (perhydroisoquinolino) silane was used instead of bis (ethylamino) dicyclopentylsilane. .
- the polymerization results are shown in Table 7.
- Example 7 2 The experiment was conducted in the same manner as in Example 9 except that (methylamino) (n-propylamino) (t_peptylamino) ethylsilane was used instead of bis (ethylamino) dicyclopentylsilane.
- the polymerization results are shown in Table 8. (Example 7 2)
- a polymerization catalyst was formed and polymerization was carried out in the same manner as in Example 9 except that 2,2-di (isobutyl) _1,3-dimethoxypropane was used instead of di-n-butyl phthalate. went.
- the results are shown in Table 4.
- a polymerization catalyst was formed and polymerization was carried out in the same manner as in Example 9, except that diethyl 2,3-n-propylsuccinate was used in place of di-n-butyrene phthalate. The results are shown in Table 4. 4 table
- novel aminosilane compound and the specific aminosilane compound of the present invention can maintain higher stereoregularity and yield of the polymer than conventional catalysts when used as a catalyst component for polymerization of olefins, and hydrogen Excellent response can be obtained. Therefore, it is possible to provide general-purpose polyolefin at a low cost and to use it in the production of polymers with high functionality that are capable of providing general-purpose polyolefin at low cost due to the ability to reduce the amount of hydrogen used during polymerization and high catalyst activity. There is expected.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
Abstract
Description
Claims
Priority Applications (7)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP06766423A EP1908767B1 (en) | 2005-05-31 | 2006-05-26 | Aminosilane compounds, catalyst components and catalysts for olefin polymerization, and process for production of olefin polymers with the same |
ES06766423T ES2389665T3 (es) | 2005-05-31 | 2006-05-26 | Compuestos aminosilánicos, componentes catalíticos y catalizadores para la polimerización de olefinas, y procedimiento para la producción de polímeros olefínicos con los mismos |
KR1020077030831A KR101234427B1 (ko) | 2005-05-31 | 2006-05-26 | 아미노실란 화합물, 올레핀류 중합용 촉매 성분 및 촉매 및이것을 이용한 올레핀류 중합체의 제조 방법 |
JP2007519075A JP5158856B2 (ja) | 2005-05-31 | 2006-05-26 | アミノシラン化合物、オレフィン類重合用触媒成分および触媒並びにこれを用いたオレフィン類重合体の製造方法 |
BRPI0611189A BRPI0611189B1 (pt) | 2005-05-31 | 2006-05-26 | catalisador para a polimerização de olefinas, e, processo para a produção de um polímero de olefina |
US11/916,039 US20100190942A1 (en) | 2005-05-31 | 2006-05-26 | Aminosilane compounds, catalyst components and catalysts for olefin polymerization, and process for production of olefin polymers with the same |
US13/289,728 US8648001B2 (en) | 2005-05-31 | 2011-11-04 | Aminosilane compounds, catalyst components and catalysts for olefin polymerization, and process for production of olefin polymers with the same |
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2005158826 | 2005-05-31 | ||
JP2005-158826 | 2005-05-31 | ||
JP2005158823 | 2005-05-31 | ||
JP2005-158823 | 2005-05-31 |
Related Child Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US11/916,039 A-371-Of-International US20100190942A1 (en) | 2005-05-31 | 2006-05-26 | Aminosilane compounds, catalyst components and catalysts for olefin polymerization, and process for production of olefin polymers with the same |
US13/289,728 Division US8648001B2 (en) | 2005-05-31 | 2011-11-04 | Aminosilane compounds, catalyst components and catalysts for olefin polymerization, and process for production of olefin polymers with the same |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2006129773A1 true WO2006129773A1 (ja) | 2006-12-07 |
Family
ID=37481701
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/JP2006/311038 WO2006129773A1 (ja) | 2005-05-31 | 2006-05-26 | アミノシラン化合物、オレフィン類重合用触媒成分および触媒並びにこれを用いたオレフィン類重合体の製造方法 |
Country Status (9)
Country | Link |
---|---|
US (2) | US20100190942A1 (ja) |
EP (1) | EP1908767B1 (ja) |
JP (1) | JP5158856B2 (ja) |
KR (1) | KR101234427B1 (ja) |
BR (1) | BRPI0611189B1 (ja) |
ES (1) | ES2389665T3 (ja) |
SG (1) | SG162730A1 (ja) |
TW (1) | TWI388579B (ja) |
WO (1) | WO2006129773A1 (ja) |
Cited By (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2008050883A1 (fr) * | 2006-10-27 | 2008-05-02 | Toho Catalyst Co., Ltd. | Procede destine a produire un copolymere bloc d'ethylene-propylene |
JP2008280472A (ja) * | 2007-05-14 | 2008-11-20 | Toho Titanium Co Ltd | オレフィン類重合用触媒及びこれを用いたオレフィン類重合体の製造方法 |
WO2008150099A2 (en) * | 2007-06-05 | 2008-12-11 | Lg Chem, Ltd. | Optically anisotropic compound and resin composition comprising the same |
WO2010106888A1 (ja) | 2009-03-17 | 2010-09-23 | 東邦チタニウム株式会社 | オレフィン類重合用固体触媒成分および触媒並びにこれを用いたオレフィン類重合体の製造方法 |
JP2011256120A (ja) * | 2010-06-07 | 2011-12-22 | Toho Titanium Co Ltd | オルガノアミノシラン化合物の製造方法 |
EP2620440A1 (en) | 2012-01-27 | 2013-07-31 | Air Products And Chemicals, Inc. | Volatile monoamino-dialkoxysilanes and their use for creating silicon-containing films |
JPWO2013027560A1 (ja) * | 2011-08-25 | 2015-03-19 | 東邦チタニウム株式会社 | オレフィン類重合用固体触媒成分の製造方法、オレフィン類重合用触媒およびオレフィン類重合体の製造方法 |
EP3056500A1 (en) | 2015-02-13 | 2016-08-17 | Air Products And Chemicals, Inc. | Bisaminoalkoxysilane compounds and methods for using same to deposit silicon-containing films |
WO2018207642A1 (ja) | 2017-05-10 | 2018-11-15 | 東邦チタニウム株式会社 | オレフィン類重合用触媒、オレフィン類重合体の製造方法およびプロピレン-α-オレフィン共重合体 |
EP4212557A2 (en) | 2022-01-14 | 2023-07-19 | Sumitomo Chemical Company, Limited | Heterophasic propylene polymerization material and olefin polymer |
Families Citing this family (23)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US8580993B2 (en) * | 2008-11-12 | 2013-11-12 | Air Products And Chemicals, Inc. | Amino vinylsilane precursors for stressed SiN films |
US8889235B2 (en) * | 2009-05-13 | 2014-11-18 | Air Products And Chemicals, Inc. | Dielectric barrier deposition using nitrogen containing precursor |
CN102781969B (zh) | 2009-12-31 | 2015-06-24 | 株式会社普利司通 | 氨基硅烷引发剂及由其制备的官能化聚合物 |
CN102453057B (zh) * | 2010-10-25 | 2014-08-06 | 中国石油化工股份有限公司 | 一种外给电子体化合物 |
CN102453045B (zh) * | 2010-10-25 | 2014-07-09 | 中国石油化工股份有限公司 | 一种含有杯芳烃基团的化合物及其制备方法 |
ES2530075T3 (es) | 2010-12-30 | 2015-02-26 | Bridgestone Corporation | Iniciadores de aminosilano y polímeros funcionalizados preparados a partir de los mismos |
MY162215A (en) * | 2011-01-19 | 2017-05-31 | China Petroleum & Chem Corp | Solid catalyst component and catalyst for olefin polymerization |
US9677178B2 (en) | 2012-01-27 | 2017-06-13 | Versum Materials Us, Llc | Alkoxyaminosilane compounds and applications thereof |
US9670294B2 (en) | 2012-07-18 | 2017-06-06 | Toho Titanium Co., Ltd. | Method for producing solid catalyst component for use in polymerization of olefin, catalyst for use in polymerization of olefin, and method for producing olefin polymer |
KR102060849B1 (ko) | 2013-02-27 | 2019-12-30 | 도호 티타늄 가부시키가이샤 | 올레핀류 중합용 고체 촉매 성분의 제조 방법, 올레핀류 중합용 촉매 및 올레핀류 중합체의 제조 방법 |
SG11201501881YA (en) | 2013-02-27 | 2015-09-29 | Toho Titanium Co Ltd | Solid catalyst component for polymerizing olefins, catalyst for polymerizing olefins, and production method for polymerized olefins |
KR102060850B1 (ko) | 2013-02-27 | 2020-02-11 | 도호 티타늄 가부시키가이샤 | 올레핀류 중합용 고체 촉매 성분의 제조 방법, 올레핀류 중합용 촉매 및 올레핀류 중합체의 제조 방법 |
CN103172653A (zh) * | 2013-04-16 | 2013-06-26 | 上海宏锐新材料科技有限公司 | 三(二甲胺基)硅烷的制备方法 |
US9593184B2 (en) | 2014-10-28 | 2017-03-14 | Formosa Plastics Corporation, Usa | Oxalic acid diamides as modifiers for polyolefin catalysts |
EP3255067B1 (en) * | 2015-01-30 | 2021-02-24 | Toho Titanium Co., Ltd. | Production method for olefin-polymerization catalyst and production method for olefin polymer |
US9777084B2 (en) | 2016-02-19 | 2017-10-03 | Formosa Plastics Corporation, Usa | Catalyst system for olefin polymerization and method for producing olefin polymer |
US11427660B2 (en) | 2016-08-17 | 2022-08-30 | Formosa Plastics Corporation, Usa | Organosilicon compounds as electron donors for olefin polymerization catalysts and methods of making and using same |
US9815920B1 (en) | 2016-10-14 | 2017-11-14 | Formosa Plastics Corporation, Usa | Olefin polymerization catalyst components and process for the production of olefin polymers therewith |
US11735413B2 (en) * | 2016-11-01 | 2023-08-22 | Versum Materials Us, Llc | Precursors and flowable CVD methods for making low-k films to fill surface features |
US10124324B1 (en) | 2017-05-09 | 2018-11-13 | Formosa Plastics Corporation, Usa | Olefin polymerization catalyst components and process for the production of olefin polymers therewith |
US10822438B2 (en) * | 2017-05-09 | 2020-11-03 | Formosa Plastics Corporation | Catalyst system for enhanced stereo-specificity of olefin polymerization and method for producing olefin polymer |
CN111295399B (zh) | 2017-11-06 | 2022-09-06 | 埃克森美孚化学专利公司 | 基于丙烯的抗冲共聚物及生产方法和设备 |
TWI762127B (zh) * | 2020-12-29 | 2022-04-21 | 臺灣塑膠工業股份有限公司 | 聚丙烯與其製作方法及熔噴纖維布 |
Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS633010A (ja) | 1986-06-24 | 1988-01-08 | Toho Titanium Co Ltd | オレフイン類重合用触媒 |
JPH01315406A (ja) | 1987-12-26 | 1989-12-20 | Toho Titanium Co Ltd | オレフイン類重合用固体触媒成分及び触媒 |
EP0578470A2 (en) | 1992-07-06 | 1994-01-12 | Nippon Oil Co. Ltd. | Process for preparing polyolefins |
JPH08157533A (ja) * | 1994-12-09 | 1996-06-18 | Sumitomo Chem Co Ltd | 環状オレフィン系共重合体の製造法 |
JP2003231711A (ja) | 2002-02-08 | 2003-08-19 | Asahi Denka Kogyo Kk | ポリオレフィン樹脂の安定化方法 |
WO2004016662A1 (ja) * | 2002-08-19 | 2004-02-26 | Ube Industries, Ltd. | α−オレフィンの重合又は共重合に用いられるα−オレフィンの重合又は重合用触媒、その触媒成分及びその触媒を用いたα−オレフィン重合方法 |
Family Cites Families (23)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3431222A (en) * | 1967-06-22 | 1969-03-04 | Monsanto Co | High temperature resistant polymeric cyclosilazanes |
FR2193864B1 (ja) * | 1972-07-31 | 1974-12-27 | Rhone Poulenc Sa | |
IT1209255B (it) | 1980-08-13 | 1989-07-16 | Montedison Spa | Catalizzatori per la polimerizzazione di olefine. |
US5494872A (en) | 1992-04-03 | 1996-02-27 | Toho Titanium Company, Ltd. | Catalyst and solid catalyst component for preparing polyolefins with broad molecular weight distribution |
JP3273211B2 (ja) * | 1993-04-26 | 2002-04-08 | 日石三菱株式会社 | ポリオレフィンの製造方法 |
JPH07292029A (ja) | 1994-04-28 | 1995-11-07 | Toho Titanium Co Ltd | オレフィン類重合用触媒および重合方法 |
US5684173A (en) | 1994-04-28 | 1997-11-04 | Toho Titanium Co., Ltd. | Organosilicon compound and ziegler-natta catalyst containing the same |
US5965478A (en) | 1995-02-13 | 1999-10-12 | Toho Titanium Co., Ltd. | Solid catalyst component and catalyst for polymerization of olefins |
EP0790257B1 (en) | 1995-09-01 | 2001-11-14 | Toho Titanium Co., Ltd. | Solid catalytic component and catalyst for polymerizing olefins |
JPH1112316A (ja) | 1997-06-26 | 1999-01-19 | Toho Titanium Co Ltd | オレフィン類重合用固体触媒成分及び触媒 |
TW396168B (en) | 1997-08-28 | 2000-07-01 | Toho Titanium K K | Solid catalyst component and catalyst for polymerization of olefins |
JP4970653B2 (ja) | 1998-12-25 | 2012-07-11 | 東邦チタニウム株式会社 | プロピレン重合用固体触媒成分及び触媒 |
WO2001081434A1 (fr) | 2000-04-24 | 2001-11-01 | Toho Titanium Co., Ltd. | Composant catalytique solide et catalyseur de polymerisation d'olefines |
WO2001081292A1 (fr) | 2000-04-24 | 2001-11-01 | Toho Titanium Co., Ltd. | Derives de diester phtalique et donneurs d'electrons |
WO2002028915A1 (fr) | 2000-09-29 | 2002-04-11 | Toho Titanium Co., Ltd. | Catalyseur de polymerisation d'olefines |
KR100575514B1 (ko) | 2001-03-30 | 2006-05-03 | 도호 캐털리스트 가부시키가이샤 | 올레핀 중합용 고체 촉매 성분 및 촉매, 및 프로필렌 블록공중합체 |
TWI253451B (en) | 2002-08-29 | 2006-04-21 | Toho Catalyst Co Ltd | Solid catalyst component, catalyst for polymerization of olefins, and polymerizing method of olefins |
JP2005320362A (ja) | 2004-05-06 | 2005-11-17 | Toho Catalyst Co Ltd | オレフィン類重合用触媒およびオレフィン類の重合方法 |
EP1790667A4 (en) | 2004-05-18 | 2011-05-18 | Toho Titanium Co Ltd | CATALYST FOR THE POLYMERIZATION OF OLEFINES AND METHOD FOR POLYMERIZING OLEFINES |
BRPI0518990A2 (pt) | 2004-12-13 | 2008-12-16 | Toho Catalyst Co Ltd | componente de catalisador sàlido, catalisador para a polimerizaÇço de olefinas, e, processo para produzir um polÍmero ou copolÍmero de olefina |
KR101314339B1 (ko) | 2005-08-08 | 2013-10-04 | 도호 티타늄 가부시키가이샤 | 올레핀류 중합용 촉매 성분 및 촉매 및 이것을 이용한올레핀류 중합체의 제조 방법 |
EP1921093A4 (en) | 2005-08-31 | 2011-07-13 | Toho Titanium Co Ltd | SOLID CATALYST COMPONENTS FOR THE OLEIN POLYMERIZATION, CATALYST AND PROCESS FOR THE PREPARATION OF OLEFIN POLYMERS THEREWITH |
JP5543430B2 (ja) | 2009-03-17 | 2014-07-09 | 東邦チタニウム株式会社 | オレフィン類重合用固体触媒成分および触媒並びにこれを用いたオレフィン類重合体の製造方法 |
-
2006
- 2006-05-26 EP EP06766423A patent/EP1908767B1/en active Active
- 2006-05-26 US US11/916,039 patent/US20100190942A1/en not_active Abandoned
- 2006-05-26 JP JP2007519075A patent/JP5158856B2/ja active Active
- 2006-05-26 KR KR1020077030831A patent/KR101234427B1/ko active IP Right Grant
- 2006-05-26 SG SG201003741-4A patent/SG162730A1/en unknown
- 2006-05-26 BR BRPI0611189A patent/BRPI0611189B1/pt active IP Right Grant
- 2006-05-26 WO PCT/JP2006/311038 patent/WO2006129773A1/ja active Application Filing
- 2006-05-26 ES ES06766423T patent/ES2389665T3/es active Active
- 2006-05-30 TW TW095119143A patent/TWI388579B/zh active
-
2011
- 2011-11-04 US US13/289,728 patent/US8648001B2/en active Active
Patent Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS633010A (ja) | 1986-06-24 | 1988-01-08 | Toho Titanium Co Ltd | オレフイン類重合用触媒 |
JPH01315406A (ja) | 1987-12-26 | 1989-12-20 | Toho Titanium Co Ltd | オレフイン類重合用固体触媒成分及び触媒 |
EP0578470A2 (en) | 1992-07-06 | 1994-01-12 | Nippon Oil Co. Ltd. | Process for preparing polyolefins |
JPH08157533A (ja) * | 1994-12-09 | 1996-06-18 | Sumitomo Chem Co Ltd | 環状オレフィン系共重合体の製造法 |
JP2003231711A (ja) | 2002-02-08 | 2003-08-19 | Asahi Denka Kogyo Kk | ポリオレフィン樹脂の安定化方法 |
WO2004016662A1 (ja) * | 2002-08-19 | 2004-02-26 | Ube Industries, Ltd. | α−オレフィンの重合又は共重合に用いられるα−オレフィンの重合又は重合用触媒、その触媒成分及びその触媒を用いたα−オレフィン重合方法 |
Non-Patent Citations (7)
Title |
---|
E. A. SEMENOVA ET AL., BULL. ACAD. SCI. USSR, CHEM. SCI., vol. 11, 1962, pages 1945 |
H.-J. RAKEBRANDT, U. KLINGENBIEL, Z. ANORG. ALLG. CHEM., vol. 623, 1997, pages 1264 |
M. L. FERREIRA ET AL., MACROMOL. CHEM. PHYS., vol. 202, 2001, pages 830 |
P. G. BELELLI ET AL., CURR. TRENDS POLYM. SCI., vol. 5, 2000, pages 79 |
R. HERBST-IRMER, PHOSPHOROUS, SULFUR AND SILICON, vol. 112, 1996, pages 185 |
RAKEBRANDT H.J. ET AL.: "Diamino-di-tert-butylsilanes. Building blocks for cyclic (SiN)2, (SiNBN)2, (SiN2Sn), and spirocyclic (SiN2)2Si, (SiN2Sn)2S compounds", ZEITSCHRIFT FUER ANORGANISCHE UND ALLGEMEINE CHEMIE, vol. 623, no. 8, 1997, pages 1264 - 1268, XP003002674 * |
See also references of EP1908767A4 |
Cited By (24)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP5235673B2 (ja) * | 2006-10-27 | 2013-07-10 | 東邦チタニウム株式会社 | エチレン・プロピレンブロック共重合体の製造方法 |
WO2008050883A1 (fr) * | 2006-10-27 | 2008-05-02 | Toho Catalyst Co., Ltd. | Procede destine a produire un copolymere bloc d'ethylene-propylene |
JP2008280472A (ja) * | 2007-05-14 | 2008-11-20 | Toho Titanium Co Ltd | オレフィン類重合用触媒及びこれを用いたオレフィン類重合体の製造方法 |
JP2014159399A (ja) * | 2007-06-05 | 2014-09-04 | Lg Chem Ltd | 光学異方性化合物及びこれを含む樹脂組成物 |
JP2010528110A (ja) * | 2007-06-05 | 2010-08-19 | エルジー・ケム・リミテッド | 光学異方性化合物及びこれを含む樹脂組成物 |
KR100993451B1 (ko) | 2007-06-05 | 2010-11-09 | 주식회사 엘지화학 | 광학 이방성 화합물 및 이를 포함하는 수지 조성물 |
WO2008150099A3 (en) * | 2007-06-05 | 2009-01-29 | Lg Chemical Ltd | Optically anisotropic compound and resin composition comprising the same |
WO2008150099A2 (en) * | 2007-06-05 | 2008-12-11 | Lg Chem, Ltd. | Optically anisotropic compound and resin composition comprising the same |
US8883952B2 (en) | 2007-06-05 | 2014-11-11 | Lg Chem, Ltd. | Optically anisotropic compound and resin composition comprising the same |
WO2010106888A1 (ja) | 2009-03-17 | 2010-09-23 | 東邦チタニウム株式会社 | オレフィン類重合用固体触媒成分および触媒並びにこれを用いたオレフィン類重合体の製造方法 |
US8426537B2 (en) | 2009-03-17 | 2013-04-23 | Toho Titanium Co., Ltd. | Solid catalyst component and catalyst for polymerization of olefins, and process for production of olefin polymers using same |
KR20160106205A (ko) | 2009-03-17 | 2016-09-09 | 도호 티타늄 가부시키가이샤 | 올레핀류 중합용 고체 촉매 성분 및 촉매 및 이를 이용한 올레핀류 중합체의 제조 방법 |
JP5543430B2 (ja) * | 2009-03-17 | 2014-07-09 | 東邦チタニウム株式会社 | オレフィン類重合用固体触媒成分および触媒並びにこれを用いたオレフィン類重合体の製造方法 |
JP2011256120A (ja) * | 2010-06-07 | 2011-12-22 | Toho Titanium Co Ltd | オルガノアミノシラン化合物の製造方法 |
JPWO2013027560A1 (ja) * | 2011-08-25 | 2015-03-19 | 東邦チタニウム株式会社 | オレフィン類重合用固体触媒成分の製造方法、オレフィン類重合用触媒およびオレフィン類重合体の製造方法 |
EP2620440A1 (en) | 2012-01-27 | 2013-07-31 | Air Products And Chemicals, Inc. | Volatile monoamino-dialkoxysilanes and their use for creating silicon-containing films |
EP3339311A1 (en) | 2012-01-27 | 2018-06-27 | Versum Materials US, LLC | Volatile monoamino-dialkoxysilanes and their use for creating silicon-containing films |
EP3056500A1 (en) | 2015-02-13 | 2016-08-17 | Air Products And Chemicals, Inc. | Bisaminoalkoxysilane compounds and methods for using same to deposit silicon-containing films |
US10421766B2 (en) | 2015-02-13 | 2019-09-24 | Versum Materials Us, Llc | Bisaminoalkoxysilane compounds and methods for using same to deposit silicon-containing films |
WO2018207642A1 (ja) | 2017-05-10 | 2018-11-15 | 東邦チタニウム株式会社 | オレフィン類重合用触媒、オレフィン類重合体の製造方法およびプロピレン-α-オレフィン共重合体 |
KR20190140484A (ko) | 2017-05-10 | 2019-12-19 | 도호 티타늄 가부시키가이샤 | 올레핀류 중합용 촉매, 올레핀류 중합체의 제조 방법 및 프로필렌-α-올레핀 공중합체 |
JPWO2018207642A1 (ja) * | 2017-05-10 | 2020-03-12 | 東邦チタニウム株式会社 | オレフィン類重合用触媒、オレフィン類重合体の製造方法およびプロピレン−α−オレフィン共重合体 |
JP7145149B2 (ja) | 2017-05-10 | 2022-09-30 | 東邦チタニウム株式会社 | オレフィン類重合用触媒、オレフィン類重合体の製造方法およびプロピレン-α-オレフィン共重合体 |
EP4212557A2 (en) | 2022-01-14 | 2023-07-19 | Sumitomo Chemical Company, Limited | Heterophasic propylene polymerization material and olefin polymer |
Also Published As
Publication number | Publication date |
---|---|
EP1908767A4 (en) | 2010-09-01 |
KR20080017412A (ko) | 2008-02-26 |
JP5158856B2 (ja) | 2013-03-06 |
US8648001B2 (en) | 2014-02-11 |
TW200704656A (en) | 2007-02-01 |
US20100190942A1 (en) | 2010-07-29 |
JPWO2006129773A1 (ja) | 2009-01-08 |
EP1908767B1 (en) | 2012-06-13 |
US20120053310A1 (en) | 2012-03-01 |
KR101234427B1 (ko) | 2013-02-18 |
BRPI0611189B1 (pt) | 2017-06-06 |
BRPI0611189A2 (pt) | 2012-10-30 |
ES2389665T3 (es) | 2012-10-30 |
EP1908767A1 (en) | 2008-04-09 |
TWI388579B (zh) | 2013-03-11 |
SG162730A1 (en) | 2010-07-29 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
WO2006129773A1 (ja) | アミノシラン化合物、オレフィン類重合用触媒成分および触媒並びにこれを用いたオレフィン類重合体の製造方法 | |
JP5348888B2 (ja) | オレフィン類重合用触媒成分および触媒並びにこれを用いたオレフィン類重合体の製造方法 | |
JP5543430B2 (ja) | オレフィン類重合用固体触媒成分および触媒並びにこれを用いたオレフィン類重合体の製造方法 | |
JP5797661B2 (ja) | オレフィン類重合用触媒およびオレフィン類重合体の製造方法 | |
US20050227856A1 (en) | Solid catalyst component for olefin polymerization and catalyst | |
JP5623760B2 (ja) | オレフィン類重合用固体触媒成分および触媒並びにこれを用いたオレフィン類重合体の製造方法 | |
JP4749726B2 (ja) | オレフィン類重合用固体触媒成分の製造方法 | |
WO2006064718A1 (ja) | オレフィン類重合用固体触媒成分および触媒並びにこれを用いたオレフィン類重合体又は共重合体の製造方法 | |
JP2010030925A (ja) | アルコキシマグネシウムの合成方法、オレフィン類重合用固体触媒成分および触媒 | |
JP2006169283A (ja) | オレフィン類重合用固体触媒成分および触媒並びにこれを用いたオレフィン類重合体又は共重合体の製造方法 | |
JP5235673B2 (ja) | エチレン・プロピレンブロック共重合体の製造方法 | |
JP2007224097A (ja) | オレフィン類重合用触媒及びこれを用いたオレフィン類重合体の製造方法 | |
JP5968888B2 (ja) | オレフィン類重合用固体触媒成分の製造方法、オレフィン類重合用触媒およびオレフィン類重合体の製造方法 | |
JP4947622B2 (ja) | オレフィン類重合用触媒及びこれを用いたオレフィン類重合体の製造方法 | |
JP2009102478A (ja) | アルコキシマグネシウムの合成方法、オレフィン類重合用固体触媒成分の製造方法および触媒 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
121 | Ep: the epo has been informed by wipo that ep was designated in this application | ||
WWE | Wipo information: entry into national phase |
Ref document number: 2007519075 Country of ref document: JP |
|
NENP | Non-entry into the national phase |
Ref country code: DE |
|
WWE | Wipo information: entry into national phase |
Ref document number: 2006766423 Country of ref document: EP |
|
WWE | Wipo information: entry into national phase |
Ref document number: 1020077030831 Country of ref document: KR |
|
NENP | Non-entry into the national phase |
Ref country code: RU |
|
WWE | Wipo information: entry into national phase |
Ref document number: 11916039 Country of ref document: US |
|
ENP | Entry into the national phase |
Ref document number: PI0611189 Country of ref document: BR Kind code of ref document: A2 Effective date: 20071129 |