JP4519952B2 - 高分子量コポリマー - Google Patents
高分子量コポリマー Download PDFInfo
- Publication number
- JP4519952B2 JP4519952B2 JP32180896A JP32180896A JP4519952B2 JP 4519952 B2 JP4519952 B2 JP 4519952B2 JP 32180896 A JP32180896 A JP 32180896A JP 32180896 A JP32180896 A JP 32180896A JP 4519952 B2 JP4519952 B2 JP 4519952B2
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- group
- mol
- mmol
- hydrogen
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 229920001577 copolymer Polymers 0.000 title claims abstract description 48
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims abstract description 36
- 239000005977 Ethylene Substances 0.000 claims abstract description 36
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims abstract description 16
- 238000000034 method Methods 0.000 claims description 48
- 239000003054 catalyst Substances 0.000 claims description 36
- -1 dimethylsilanediyl group Chemical group 0.000 claims description 31
- 229920000642 polymer Polymers 0.000 claims description 31
- 239000001257 hydrogen Substances 0.000 claims description 24
- 229910052739 hydrogen Inorganic materials 0.000 claims description 24
- 125000003118 aryl group Chemical group 0.000 claims description 17
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 16
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
- 150000002431 hydrogen Chemical class 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 7
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 7
- 125000004429 atom Chemical group 0.000 claims description 6
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 229910052726 zirconium Inorganic materials 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- 230000000379 polymerizing effect Effects 0.000 claims 1
- 150000001336 alkenes Chemical class 0.000 abstract description 14
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 abstract description 11
- 125000000217 alkyl group Chemical group 0.000 abstract description 9
- 125000004432 carbon atom Chemical group C* 0.000 abstract description 9
- 101150068479 chrb gene Proteins 0.000 abstract 1
- 229920002959 polymer blend Polymers 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 135
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 85
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 70
- 239000000243 solution Substances 0.000 description 58
- 238000006116 polymerization reaction Methods 0.000 description 54
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 44
- 239000000203 mixture Substances 0.000 description 40
- 239000002904 solvent Substances 0.000 description 37
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 36
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 33
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 29
- 238000006243 chemical reaction Methods 0.000 description 29
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 26
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 26
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 26
- 238000005160 1H NMR spectroscopy Methods 0.000 description 24
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 24
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
- 238000010992 reflux Methods 0.000 description 21
- 239000000725 suspension Substances 0.000 description 21
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
- 229920006395 saturated elastomer Polymers 0.000 description 20
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 19
- 239000011541 reaction mixture Substances 0.000 description 19
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 18
- VPGLGRNSAYHXPY-UHFFFAOYSA-L zirconium(2+);dichloride Chemical compound Cl[Zr]Cl VPGLGRNSAYHXPY-UHFFFAOYSA-L 0.000 description 18
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 17
- 239000012074 organic phase Substances 0.000 description 17
- 239000000047 product Substances 0.000 description 16
- 239000000741 silica gel Substances 0.000 description 16
- 229910002027 silica gel Inorganic materials 0.000 description 16
- 150000001875 compounds Chemical class 0.000 description 15
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 14
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 14
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 14
- 229910007928 ZrCl2 Inorganic materials 0.000 description 13
- 229910000077 silane Inorganic materials 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 229910052782 aluminium Inorganic materials 0.000 description 12
- 235000017557 sodium bicarbonate Nutrition 0.000 description 12
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 12
- 239000007787 solid Substances 0.000 description 12
- 238000003756 stirring Methods 0.000 description 12
- 229920001400 block copolymer Polymers 0.000 description 11
- 239000007789 gas Substances 0.000 description 11
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 10
- 230000000694 effects Effects 0.000 description 10
- 238000001914 filtration Methods 0.000 description 9
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 9
- 235000019341 magnesium sulphate Nutrition 0.000 description 9
- 239000000178 monomer Substances 0.000 description 9
- 239000000843 powder Substances 0.000 description 9
- XOJVVFBFDXDTEG-UHFFFAOYSA-N pristane Chemical compound CC(C)CCCC(C)CCCC(C)CCCC(C)C XOJVVFBFDXDTEG-UHFFFAOYSA-N 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- DUNKXUFBGCUVQW-UHFFFAOYSA-J zirconium tetrachloride Chemical compound Cl[Zr](Cl)(Cl)Cl DUNKXUFBGCUVQW-UHFFFAOYSA-J 0.000 description 9
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 8
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 8
- LIKFHECYJZWXFJ-UHFFFAOYSA-N dimethyldichlorosilane Chemical compound C[Si](C)(Cl)Cl LIKFHECYJZWXFJ-UHFFFAOYSA-N 0.000 description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 8
- 239000012442 inert solvent Substances 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- 238000002844 melting Methods 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 8
- 229920005604 random copolymer Polymers 0.000 description 8
- 239000011780 sodium chloride Substances 0.000 description 8
- 238000009835 boiling Methods 0.000 description 7
- 239000013078 crystal Substances 0.000 description 7
- 229920001519 homopolymer Polymers 0.000 description 7
- 150000002430 hydrocarbons Chemical group 0.000 description 7
- 238000001819 mass spectrum Methods 0.000 description 7
- 235000019260 propionic acid Nutrition 0.000 description 7
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 6
- OJVWBQRZCJLURF-UHFFFAOYSA-L C1=CC=C2C(C3=CC=CC4=C3C=C(C)C4[Zr](Cl)(Cl)(C3C4=C(C(=CC=C4)C=4C5=CC=CC=C5C=CC=4)C=C3C)=[Si](C)C)=CC=CC2=C1 Chemical compound C1=CC=C2C(C3=CC=CC4=C3C=C(C)C4[Zr](Cl)(Cl)(C3C4=C(C(=CC=C4)C=4C5=CC=CC=C5C=CC=4)C=C3C)=[Si](C)C)=CC=CC2=C1 OJVWBQRZCJLURF-UHFFFAOYSA-L 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 125000001931 aliphatic group Chemical group 0.000 description 6
- 229910052786 argon Inorganic materials 0.000 description 6
- 239000012230 colorless oil Substances 0.000 description 6
- 239000012043 crude product Substances 0.000 description 6
- UPQZOUHVTJNGFK-UHFFFAOYSA-N diethyl 2-methylpropanedioate Chemical compound CCOC(=O)C(C)C(=O)OCC UPQZOUHVTJNGFK-UHFFFAOYSA-N 0.000 description 6
- 229920001971 elastomer Polymers 0.000 description 6
- 230000009477 glass transition Effects 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
- MPCBCIIAQIDKTH-UHFFFAOYSA-N 7-[3,5-di(propan-2-yl)phenyl]-2-methyl-1h-indene Chemical compound CC(C)C1=CC(C(C)C)=CC(C=2C=3CC(C)=CC=3C=CC=2)=C1 MPCBCIIAQIDKTH-UHFFFAOYSA-N 0.000 description 5
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 5
- NDJMNNSJDIFFTH-UHFFFAOYSA-L [Cl-].[Cl-].CC1=CC(C(=CC=C2)C=3C=CC=CC=3)=C2C1[Zr+2]([SiH](C)C)C1C(C)=CC2=C1C=CC=C2C1=CC=CC=C1 Chemical compound [Cl-].[Cl-].CC1=CC(C(=CC=C2)C=3C=CC=CC=3)=C2C1[Zr+2]([SiH](C)C)C1C(C)=CC2=C1C=CC=C2C1=CC=CC=C1 NDJMNNSJDIFFTH-UHFFFAOYSA-L 0.000 description 5
- 239000008346 aqueous phase Substances 0.000 description 5
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 5
- 238000007334 copolymerization reaction Methods 0.000 description 5
- 150000001993 dienes Chemical class 0.000 description 5
- 238000005194 fractionation Methods 0.000 description 5
- 229930195733 hydrocarbon Natural products 0.000 description 5
- 239000003446 ligand Substances 0.000 description 5
- CPOFMOWDMVWCLF-UHFFFAOYSA-N methyl(oxo)alumane Chemical compound C[Al]=O CPOFMOWDMVWCLF-UHFFFAOYSA-N 0.000 description 5
- 239000003208 petroleum Substances 0.000 description 5
- 238000000746 purification Methods 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 5
- 229920001897 terpolymer Polymers 0.000 description 5
- MCULRUJILOGHCJ-UHFFFAOYSA-N triisobutylaluminium Chemical compound CC(C)C[Al](CC(C)C)CC(C)C MCULRUJILOGHCJ-UHFFFAOYSA-N 0.000 description 5
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 4
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 4
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 4
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 4
- WSSSPWUEQFSQQG-UHFFFAOYSA-N 4-methyl-1-pentene Chemical compound CC(C)CC=C WSSSPWUEQFSQQG-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- QRLWANGDYKYFOR-UHFFFAOYSA-N C(C)(C)C=1C=C2C=CCC2=C(C1)C1=CC=CC2=CC=CC=C12 Chemical compound C(C)(C)C=1C=C2C=CCC2=C(C1)C1=CC=CC2=CC=CC=C12 QRLWANGDYKYFOR-UHFFFAOYSA-N 0.000 description 4
- QBPATROIDJMBJY-UHFFFAOYSA-L CC1=Cc2c(cccc2-c2ccc3ccccc3c2)C1[Zr](Cl)(Cl)(C1C(C)=Cc2c1cccc2-c1ccc2ccccc2c1)=[Si](C)C Chemical compound CC1=Cc2c(cccc2-c2ccc3ccccc3c2)C1[Zr](Cl)(Cl)(C1C(C)=Cc2c1cccc2-c1ccc2ccccc2c1)=[Si](C)C QBPATROIDJMBJY-UHFFFAOYSA-L 0.000 description 4
- 239000004215 Carbon black (E152) Substances 0.000 description 4
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 4
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 4
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 4
- 229910006124 SOCl2 Inorganic materials 0.000 description 4
- 238000004587 chromatography analysis Methods 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 239000011777 magnesium Substances 0.000 description 4
- 229910052749 magnesium Inorganic materials 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 238000004806 packaging method and process Methods 0.000 description 4
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- OJOWICOBYCXEKR-KRXBUXKQSA-N (5e)-5-ethylidenebicyclo[2.2.1]hept-2-ene Chemical compound C1C2C(=C/C)/CC1C=C2 OJOWICOBYCXEKR-KRXBUXKQSA-N 0.000 description 3
- QSSXJPIWXQTSIX-UHFFFAOYSA-N 1-bromo-2-methylbenzene Chemical compound CC1=CC=CC=C1Br QSSXJPIWXQTSIX-UHFFFAOYSA-N 0.000 description 3
- NKFNCOZXYIKUMD-UHFFFAOYSA-N 2-methyl-7-phenyl-5-propan-2-yl-1h-indene Chemical compound C=1C(C(C)C)=CC=2C=C(C)CC=2C=1C1=CC=CC=C1 NKFNCOZXYIKUMD-UHFFFAOYSA-N 0.000 description 3
- YQMLGDDBGRGBAW-UHFFFAOYSA-L CC1=Cc2c(cccc2-c2cc3ccccc3c3ccccc23)C1[Zr](Cl)(Cl)(C1C(C)=Cc2c1cccc2-c1cc2ccccc2c2ccccc12)=[Si](C)C Chemical compound CC1=Cc2c(cccc2-c2cc3ccccc3c3ccccc23)C1[Zr](Cl)(Cl)(C1C(C)=Cc2c1cccc2-c1cc2ccccc2c2ccccc12)=[Si](C)C YQMLGDDBGRGBAW-UHFFFAOYSA-L 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- CHUSCWNZYTZYRP-UHFFFAOYSA-L [Cl-].[Cl-].C[Si](=[Zr+2](C1C(=CC2=C(C=C(C=C12)C(C)C)C1=CC=CC=C1)C)C1C(=CC2=C(C=C(C=C12)C(C)C)C1=CC=CC=C1)C)C Chemical compound [Cl-].[Cl-].C[Si](=[Zr+2](C1C(=CC2=C(C=C(C=C12)C(C)C)C1=CC=CC=C1)C)C1C(=CC2=C(C=C(C=C12)C(C)C)C1=CC=CC=C1)C)C CHUSCWNZYTZYRP-UHFFFAOYSA-L 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 239000002283 diesel fuel Substances 0.000 description 3
- SMBQBQBNOXIFSF-UHFFFAOYSA-N dilithium Chemical class [Li][Li] SMBQBQBNOXIFSF-UHFFFAOYSA-N 0.000 description 3
- 238000009826 distribution Methods 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 235000013305 food Nutrition 0.000 description 3
- 238000000465 moulding Methods 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 125000000538 pentafluorophenyl group Chemical group FC1=C(F)C(F)=C(*)C(F)=C1F 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 229910052710 silicon Inorganic materials 0.000 description 3
- 239000010703 silicon Substances 0.000 description 3
- KEAYESYHFKHZAL-IGMARMGPSA-N sodium-23 atom Chemical compound [23Na] KEAYESYHFKHZAL-IGMARMGPSA-N 0.000 description 3
- VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 description 3
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 3
- VQSMDEGMFQYKRS-UHFFFAOYSA-N 1-(2-methyl-3h-inden-4-yl)naphthalene Chemical compound C1=CC=C2C(C=3C=CC=C4C=C(CC4=3)C)=CC=CC2=C1 VQSMDEGMFQYKRS-UHFFFAOYSA-N 0.000 description 2
- RGDQEELGYQIORT-UHFFFAOYSA-N 1-(2-methyl-6-propan-2-yl-3h-inden-4-yl)naphthalene Chemical compound C1=CC=C2C(C=3C=4CC(C)=CC=4C=C(C=3)C(C)C)=CC=CC2=C1 RGDQEELGYQIORT-UHFFFAOYSA-N 0.000 description 2
- DRFPSPRQWNZEMK-UHFFFAOYSA-N 1-(2-methylphenyl)naphthalene Chemical compound CC1=CC=CC=C1C1=CC=CC2=CC=CC=C12 DRFPSPRQWNZEMK-UHFFFAOYSA-N 0.000 description 2
- OSVDDXPBWUGMFB-UHFFFAOYSA-N 1-[2-(bromomethyl)phenyl]naphthalene Chemical compound BrCC1=CC=CC=C1C1=CC=CC2=CC=CC=C12 OSVDDXPBWUGMFB-UHFFFAOYSA-N 0.000 description 2
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 2
- CMHWKURALISWAN-UHFFFAOYSA-N 2-(2-methyl-3h-inden-4-yl)naphthalene Chemical compound C1=CC=CC2=CC(C=3C=CC=C4C=C(CC4=3)C)=CC=C21 CMHWKURALISWAN-UHFFFAOYSA-N 0.000 description 2
- FCVQDADWCGVNDK-UHFFFAOYSA-N 2-(2-methylphenyl)naphthalene Chemical compound CC1=CC=CC=C1C1=CC=C(C=CC=C2)C2=C1 FCVQDADWCGVNDK-UHFFFAOYSA-N 0.000 description 2
- GJVSHKYHUSYPAG-UHFFFAOYSA-N 2-[2-(bromomethyl)phenyl]naphthalene Chemical compound BrCC1=CC=CC=C1C1=CC=C(C=CC=C2)C2=C1 GJVSHKYHUSYPAG-UHFFFAOYSA-N 0.000 description 2
- SHFAECXTNMEMCW-UHFFFAOYSA-N 2-methyl-3-(2-naphthalen-1-ylphenyl)propanoic acid Chemical compound OC(=O)C(C)CC1=CC=CC=C1C1=CC=CC2=CC=CC=C12 SHFAECXTNMEMCW-UHFFFAOYSA-N 0.000 description 2
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- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F210/00—Copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
- C08F210/04—Monomers containing three or four carbon atoms
- C08F210/06—Propene
-
- 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
- C08F210/00—Copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
- C08F210/16—Copolymers of ethene with alpha-alkenes, e.g. EP rubbers
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F4/00—Polymerisation catalysts
- C08F4/42—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors
- C08F4/44—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides
- C08F4/60—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides together with refractory metals, iron group metals, platinum group metals, manganese, rhenium technetium or compounds thereof
- C08F4/619—Component covered by group C08F4/60 containing a transition metal-carbon bond
- C08F4/61912—Component covered by group C08F4/60 containing a transition metal-carbon bond in combination with an organoaluminium compound
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F4/00—Polymerisation catalysts
- C08F4/42—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors
- C08F4/44—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides
- C08F4/60—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides together with refractory metals, iron group metals, platinum group metals, manganese, rhenium technetium or compounds thereof
- C08F4/619—Component covered by group C08F4/60 containing a transition metal-carbon bond
- C08F4/61916—Component covered by group C08F4/60 containing a transition metal-carbon bond supported on a carrier, e.g. silica, MgCl2, polymer
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F4/00—Polymerisation catalysts
- C08F4/42—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors
- C08F4/44—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides
- C08F4/60—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides together with refractory metals, iron group metals, platinum group metals, manganese, rhenium technetium or compounds thereof
- C08F4/619—Component covered by group C08F4/60 containing a transition metal-carbon bond
- C08F4/6192—Component covered by group C08F4/60 containing a transition metal-carbon bond containing at least one cyclopentadienyl ring, condensed or not, e.g. an indenyl or a fluorenyl ring
- C08F4/61922—Component covered by group C08F4/60 containing a transition metal-carbon bond containing at least one cyclopentadienyl ring, condensed or not, e.g. an indenyl or a fluorenyl ring containing at least two cyclopentadienyl rings, fused or not
- C08F4/61927—Component covered by group C08F4/60 containing a transition metal-carbon bond containing at least one cyclopentadienyl ring, condensed or not, e.g. an indenyl or a fluorenyl ring containing at least two cyclopentadienyl rings, fused or not two cyclopentadienyl rings being mutually bridged
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S526/00—Synthetic resins or natural rubbers -- part of the class 520 series
- Y10S526/943—Polymerization with metallocene catalysts
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Manufacture Of Macromolecular Shaped Articles (AREA)
- Food Preservation Except Freezing, Refrigeration, And Drying (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19544828.6 | 1995-12-01 | ||
| DE19544828A DE19544828A1 (de) | 1995-12-01 | 1995-12-01 | Hochmolekulare Copolymere |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JPH09176222A JPH09176222A (ja) | 1997-07-08 |
| JPH09176222A5 JPH09176222A5 (enExample) | 2004-11-11 |
| JP4519952B2 true JP4519952B2 (ja) | 2010-08-04 |
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|---|---|---|---|
| JP32180896A Expired - Lifetime JP4519952B2 (ja) | 1995-12-01 | 1996-12-02 | 高分子量コポリマー |
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|---|---|
| US (1) | US6057408A (enExample) |
| EP (2) | EP1270614B1 (enExample) |
| JP (1) | JP4519952B2 (enExample) |
| AT (2) | ATE456589T1 (enExample) |
| BR (1) | BR9605779A (enExample) |
| CA (1) | CA2191661A1 (enExample) |
| DE (3) | DE19544828A1 (enExample) |
| ES (1) | ES2216031T3 (enExample) |
| NO (1) | NO310877B1 (enExample) |
| TW (1) | TW454021B (enExample) |
| ZA (1) | ZA9610051B (enExample) |
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| JP3176932B2 (ja) | 1995-10-18 | 2001-06-18 | チッソ株式会社 | オレフィン（共）重合体組成物とその製造方法及びオレフィン（共）重合用触媒とその製造方法 |
| SG67392A1 (en) * | 1996-05-27 | 1999-09-21 | Sumitomo Chemical Co | Propylene/ethylene-alpha-olefin block copolymer and process for producing the same |
| US6303696B1 (en) * | 1997-04-11 | 2001-10-16 | Chisso Corporation | Propylene (co)polymer composition using metallocene catalyst |
| US6818585B2 (en) * | 1998-12-30 | 2004-11-16 | Univation Technologies, Llc | Catalyst compounds, catalyst systems thereof and their use in a polymerization process |
| CA2398529A1 (en) | 2000-02-08 | 2001-08-16 | Exxonmobil Chemical Patents Inc. | Method of preparing group 14 bridged biscyclopentadienyl ligands |
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| US6380122B1 (en) | 2000-06-30 | 2002-04-30 | Exxonmobil Chemical Patents Inc. | Metallocene compositions |
| US6376409B1 (en) | 2000-06-30 | 2002-04-23 | Exxonmobil Chemical Patents Inc. | Metallocene compositions |
| US6376413B1 (en) | 2000-06-30 | 2002-04-23 | Exxonmobil Chemical Patents Inc. | Metallocene compositions |
| US6380123B1 (en) | 2000-06-30 | 2002-04-30 | Exxonmobil Chemical Patents Inc. | Metallocene compositions |
| US6380330B1 (en) | 2000-06-30 | 2002-04-30 | Exxonmobil Chemical Patents Inc. | Metallocene compositions |
| WO2002002576A1 (en) * | 2000-06-30 | 2002-01-10 | Exxonmobil Chemical Patents Inc. | Bridged bis (indenyl) metallocene compounds |
| US6380331B1 (en) | 2000-06-30 | 2002-04-30 | Exxonmobil Chemical Patents Inc. | Metallocene compositions |
| US6376412B1 (en) | 2000-06-30 | 2002-04-23 | Exxonmobil Chemical Patents Inc. | Metallocene compositions |
| US6380120B1 (en) | 2000-06-30 | 2002-04-30 | Exxonmobil Chemical Patents Inc. | Metallocene compositions |
| US6376627B1 (en) | 2000-06-30 | 2002-04-23 | Exxonmobil Chemical Patents Inc. | Metallocene compositions |
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| US6376408B1 (en) | 2000-06-30 | 2002-04-23 | Exxonmobil Chemical Patents Inc. | Metallocene compositions |
| US6414095B1 (en) | 2000-06-30 | 2002-07-02 | Exxon Mobil Chemical Patents Inc. | Metallocene compositions |
| US6376411B1 (en) | 2000-06-30 | 2002-04-23 | Exxonmobil Chemical Patents Inc. | Metallocene compositions |
| US6376410B1 (en) | 2000-06-30 | 2002-04-23 | Exxonmobil Chemical Patents Inc. | Metallocene compositions |
| US6380121B1 (en) | 2000-06-30 | 2002-04-30 | Exxonmobil Chemical Patents Inc. | Metallocene compositions |
| US7122498B2 (en) | 2000-06-30 | 2006-10-17 | Exxonmobil Chemical Patents Inc. | Metallocenes and catalyst compositions derived therefrom |
| US6376407B1 (en) | 2000-06-30 | 2002-04-23 | Exxonmobil Chemical Patents Inc. | Metallocene compositions |
| US6380124B1 (en) | 2000-06-30 | 2002-04-30 | Exxonmobil Chemical Patents Inc. | Metallocene compositions |
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| ATE445650T1 (de) * | 2004-05-04 | 2009-10-15 | Basell Polyolefine Gmbh | Verfahren zur herstellung von ataktischen 1- butenpolymeren |
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| US7169864B2 (en) * | 2004-12-01 | 2007-01-30 | Novolen Technology Holdings, C.V. | Metallocene catalysts, their synthesis and their use for the polymerization of olefins |
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| TW200745003A (en) | 2005-10-06 | 2007-12-16 | Astrazeneca Ab | Novel compounds |
| JP2009530341A (ja) * | 2006-03-17 | 2009-08-27 | バーゼル・ポリオレフィン・ゲーエムベーハー | メタロセン化合物類 |
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| EP2495037B1 (en) | 2011-03-02 | 2020-08-19 | Borealis AG | High throughput reactor assembly for polymerization of olefins |
| ES2817776T3 (es) | 2011-03-02 | 2021-04-08 | Borealis Ag | Un procedimiento para la producción de polímeros |
| ES2605429T3 (es) | 2011-06-15 | 2017-03-14 | Borealis Ag | Mezcla del reactor in situ de un polipropileno nucleado catalizado por Ziegler-Natta y un polipropileno catalizado por metaloceno |
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| EP2573091A1 (en) | 2011-09-23 | 2013-03-27 | Lummus Novolen Technology Gmbh | Process for recycling of free ligand from their corresponding metallocene complexes |
| US9382359B2 (en) | 2012-08-29 | 2016-07-05 | Borealis Ag | Reactor assembly and method for polymerization of olefins |
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| EP3124567A1 (en) | 2015-07-30 | 2017-02-01 | Borealis AG | Polypropylene based hot-melt adhesive composition |
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| US11807655B2 (en) | 2016-12-29 | 2023-11-07 | Borealis Ag | Catalysts |
| JP7027988B2 (ja) | 2017-04-27 | 2022-03-02 | 住友化学株式会社 | プロピレン重合体組成物 |
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| US20210277290A1 (en) | 2018-08-06 | 2021-09-09 | Borealis Ag | Propylene random copolymer based hot melt adhesive composition |
| EP3608364A1 (en) | 2018-08-06 | 2020-02-12 | Borealis AG | Multimodal propylene random copolymer based composition suitable as hot melt adhesive composition |
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| WO2021083309A1 (zh) | 2019-10-30 | 2021-05-06 | 中国石油化工股份有限公司 | 一种茂金属化合物及其制备方法和应用 |
| TW202309112A (zh) | 2021-04-25 | 2023-03-01 | 大陸商中國石油化工科技開發有限公司 | 丙烯基共聚物、其製備方法和用途和包含其的聚丙烯組合物 |
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| JPS59204646A (ja) * | 1983-05-09 | 1984-11-20 | Japan Synthetic Rubber Co Ltd | ポリプロピレン樹脂組成物 |
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-
1995
- 1995-12-01 DE DE19544828A patent/DE19544828A1/de not_active Ceased
-
1996
- 1996-11-26 DE DE59611505T patent/DE59611505D1/de not_active Expired - Lifetime
- 1996-11-26 AT AT02019624T patent/ATE456589T1/de not_active IP Right Cessation
- 1996-11-26 DE DE59610907T patent/DE59610907D1/de not_active Expired - Lifetime
- 1996-11-26 AT AT96118856T patent/ATE258940T1/de not_active IP Right Cessation
- 1996-11-26 ES ES96118856T patent/ES2216031T3/es not_active Expired - Lifetime
- 1996-11-26 EP EP02019624A patent/EP1270614B1/de not_active Expired - Lifetime
- 1996-11-26 EP EP96118856A patent/EP0776913B1/de not_active Expired - Lifetime
- 1996-11-28 TW TW085114702A patent/TW454021B/zh not_active IP Right Cessation
- 1996-11-29 ZA ZA9610051A patent/ZA9610051B/xx unknown
- 1996-11-29 CA CA002191661A patent/CA2191661A1/en not_active Abandoned
- 1996-11-29 NO NO19965106A patent/NO310877B1/no not_active IP Right Cessation
- 1996-12-02 BR BR9605779A patent/BR9605779A/pt active Search and Examination
- 1996-12-02 JP JP32180896A patent/JP4519952B2/ja not_active Expired - Lifetime
-
1998
- 1998-04-13 US US09/058,828 patent/US6057408A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| DE19544828A1 (de) | 1997-06-05 |
| EP0776913A3 (de) | 1998-09-02 |
| NO965106D0 (no) | 1996-11-29 |
| NO965106L (no) | 1997-06-02 |
| EP1270614A3 (de) | 2004-12-22 |
| EP0776913B1 (de) | 2004-02-04 |
| ES2216031T3 (es) | 2004-10-16 |
| NO310877B1 (no) | 2001-09-10 |
| ATE456589T1 (de) | 2010-02-15 |
| EP1270614A2 (de) | 2003-01-02 |
| CA2191661A1 (en) | 1997-06-02 |
| ZA9610051B (en) | 1997-06-01 |
| EP0776913A2 (de) | 1997-06-04 |
| DE59611505D1 (de) | 2010-03-18 |
| EP1270614B1 (de) | 2010-01-27 |
| TW454021B (en) | 2001-09-11 |
| ATE258940T1 (de) | 2004-02-15 |
| BR9605779A (pt) | 1998-08-25 |
| DE59610907D1 (de) | 2004-03-11 |
| JPH09176222A (ja) | 1997-07-08 |
| US6057408A (en) | 2000-05-02 |
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