DE19544828A1 - Hochmolekulare Copolymere - Google Patents
Hochmolekulare CopolymereInfo
- Publication number
- DE19544828A1 DE19544828A1 DE19544828A DE19544828A DE19544828A1 DE 19544828 A1 DE19544828 A1 DE 19544828A1 DE 19544828 A DE19544828 A DE 19544828A DE 19544828 A DE19544828 A DE 19544828A DE 19544828 A1 DE19544828 A1 DE 19544828A1
- Authority
- DE
- Germany
- Prior art keywords
- group
- methyl
- hydrogen
- radicals
- mol
- 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.)
- Ceased
Links
- 229920001577 copolymer Polymers 0.000 title claims abstract description 60
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims abstract description 38
- 239000005977 Ethylene Substances 0.000 claims abstract description 38
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims abstract description 21
- 150000001336 alkenes Chemical class 0.000 claims abstract description 18
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 13
- 238000006116 polymerization reaction Methods 0.000 claims description 49
- 239000003054 catalyst Substances 0.000 claims description 47
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 37
- 229920000642 polymer Polymers 0.000 claims description 34
- 125000003118 aryl group Chemical group 0.000 claims description 32
- 239000001257 hydrogen Substances 0.000 claims description 31
- 229910052739 hydrogen Inorganic materials 0.000 claims description 31
- 238000000034 method Methods 0.000 claims description 29
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 24
- 150000001875 compounds Chemical class 0.000 claims description 16
- 238000004519 manufacturing process Methods 0.000 claims description 15
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 14
- 229920001400 block copolymer Polymers 0.000 claims description 12
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 12
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 11
- 229920006301 statistical copolymer Polymers 0.000 claims description 11
- 125000004429 atom Chemical group 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 8
- 125000001931 aliphatic group Chemical group 0.000 claims description 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 8
- 229920001971 elastomer Polymers 0.000 claims description 7
- 239000005060 rubber Substances 0.000 claims description 7
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 claims description 6
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 claims description 6
- WSSSPWUEQFSQQG-UHFFFAOYSA-N 4-methyl-1-pentene Chemical compound CC(C)CC=C WSSSPWUEQFSQQG-UHFFFAOYSA-N 0.000 claims description 6
- 150000001993 dienes Chemical class 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
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 claims description 6
- 150000002431 hydrogen Chemical class 0.000 claims description 5
- 229910052751 metal Inorganic materials 0.000 claims description 5
- 239000002184 metal Substances 0.000 claims description 5
- 229910052710 silicon Inorganic materials 0.000 claims description 5
- 239000010703 silicon Substances 0.000 claims description 5
- OJOWICOBYCXEKR-KRXBUXKQSA-N (5e)-5-ethylidenebicyclo[2.2.1]hept-2-ene Chemical compound C1C2C(=C/C)/CC1C=C2 OJOWICOBYCXEKR-KRXBUXKQSA-N 0.000 claims description 4
- 238000000465 moulding Methods 0.000 claims description 4
- 238000004806 packaging method and process Methods 0.000 claims description 4
- 125000000538 pentafluorophenyl group Chemical group FC1=C(F)C(F)=C(*)C(F)=C1F 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 229910052723 transition metal Inorganic materials 0.000 claims description 4
- 150000003624 transition metals Chemical class 0.000 claims description 4
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 3
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 3
- 125000006725 C1-C10 alkenyl group Chemical group 0.000 claims description 3
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 229910052732 germanium Inorganic materials 0.000 claims description 3
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- 229910052726 zirconium Inorganic materials 0.000 claims description 3
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 108010063256 HTLV-1 protease Proteins 0.000 claims description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 230000009477 glass transition Effects 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 238000001746 injection moulding Methods 0.000 claims description 2
- 230000000737 periodic effect Effects 0.000 claims description 2
- 229910052718 tin Inorganic materials 0.000 claims description 2
- 239000000956 alloy Substances 0.000 claims 1
- 229910045601 alloy Inorganic materials 0.000 claims 1
- 230000000379 polymerizing effect Effects 0.000 claims 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 abstract description 9
- 125000000217 alkyl group Chemical group 0.000 abstract description 2
- 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 147
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 81
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 79
- 239000000243 solution Substances 0.000 description 57
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 48
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 44
- -1 C1-C10 Chemical group 0.000 description 37
- 239000002904 solvent Substances 0.000 description 36
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical class [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 35
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 32
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 31
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 30
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 28
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 27
- 238000005160 1H NMR spectroscopy Methods 0.000 description 24
- 150000003254 radicals Chemical class 0.000 description 24
- 239000000725 suspension Substances 0.000 description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 22
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 20
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 20
- 239000000203 mixture Substances 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
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 18
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 18
- 239000012074 organic phase Substances 0.000 description 17
- 238000010992 reflux Methods 0.000 description 17
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 15
- 229910000077 silane Inorganic materials 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
- 238000006243 chemical reaction Methods 0.000 description 13
- 239000000741 silica gel Substances 0.000 description 13
- 229910002027 silica gel Inorganic materials 0.000 description 13
- 239000007787 solid Substances 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 229910007928 ZrCl2 Inorganic materials 0.000 description 12
- VPGLGRNSAYHXPY-UHFFFAOYSA-L zirconium(2+);dichloride Chemical compound Cl[Zr]Cl VPGLGRNSAYHXPY-UHFFFAOYSA-L 0.000 description 12
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 10
- 229910052782 aluminium Inorganic materials 0.000 description 10
- 229910052786 argon Inorganic materials 0.000 description 10
- 239000013078 crystal Substances 0.000 description 10
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 10
- 230000000694 effects Effects 0.000 description 10
- 239000007789 gas Substances 0.000 description 9
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 9
- 235000019341 magnesium sulphate Nutrition 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 239000011734 sodium Substances 0.000 description 9
- 239000012279 sodium borohydride Substances 0.000 description 9
- 229910000033 sodium borohydride Inorganic materials 0.000 description 9
- 239000011780 sodium chloride Substances 0.000 description 9
- DUNKXUFBGCUVQW-UHFFFAOYSA-J zirconium tetrachloride Chemical compound Cl[Zr](Cl)(Cl)Cl DUNKXUFBGCUVQW-UHFFFAOYSA-J 0.000 description 9
- 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 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
- 239000012442 inert solvent Substances 0.000 description 8
- 238000002844 melting Methods 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- 239000000178 monomer Substances 0.000 description 8
- 239000000843 powder Substances 0.000 description 8
- 229910052708 sodium Inorganic materials 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 7
- 238000001914 filtration Methods 0.000 description 7
- 229920001519 homopolymer Polymers 0.000 description 7
- 229930195733 hydrocarbon Natural products 0.000 description 7
- 238000001819 mass spectrum Methods 0.000 description 7
- XOJVVFBFDXDTEG-UHFFFAOYSA-N pristane Chemical compound CC(C)CCCC(C)CCCC(C)CCCC(C)C XOJVVFBFDXDTEG-UHFFFAOYSA-N 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- 239000004215 Carbon black (E152) Substances 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 6
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 239000012230 colorless oil Substances 0.000 description 6
- 238000007334 copolymerization reaction Methods 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
- 239000003921 oil Substances 0.000 description 6
- 239000000377 silicon dioxide Substances 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- 229920001897 terpolymer Polymers 0.000 description 6
- 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 5
- 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 5
- 229910006124 SOCl2 Inorganic materials 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
- 238000005194 fractionation Methods 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- 150000002430 hydrocarbons Chemical class 0.000 description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
- 239000003446 ligand Substances 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 239000012071 phase Substances 0.000 description 5
- 235000019260 propionic acid Nutrition 0.000 description 5
- 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 5
- 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 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
- 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
- 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
- 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 4
- 239000008346 aqueous phase Substances 0.000 description 4
- 239000012876 carrier material Substances 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
- 239000002244 precipitate Substances 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 4
- 239000000375 suspending agent Substances 0.000 description 4
- MCULRUJILOGHCJ-UHFFFAOYSA-N triisobutylaluminium Chemical compound CC(C)C[Al](CC(C)C)CC(C)C MCULRUJILOGHCJ-UHFFFAOYSA-N 0.000 description 4
- QSSXJPIWXQTSIX-UHFFFAOYSA-N 1-bromo-2-methylbenzene Chemical compound CC1=CC=CC=C1Br QSSXJPIWXQTSIX-UHFFFAOYSA-N 0.000 description 3
- YXNLSABUBHHJCY-UHFFFAOYSA-N 2-methyl-3-(2-naphthalen-2-ylphenyl)propanoic acid Chemical compound OC(=O)C(C)CC1=CC=CC=C1C1=CC=C(C=CC=C2)C2=C1 YXNLSABUBHHJCY-UHFFFAOYSA-N 0.000 description 3
- VHIKUGITLWELJA-UHFFFAOYSA-N 2-methyl-3-(2-phenylphenyl)propanoic acid Chemical compound OC(=O)C(C)CC1=CC=CC=C1C1=CC=CC=C1 VHIKUGITLWELJA-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
- 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 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 229910052681 coesite Inorganic materials 0.000 description 3
- 229910052906 cristobalite Inorganic materials 0.000 description 3
- 239000002283 diesel fuel Substances 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 239000000499 gel Substances 0.000 description 3
- CPOFMOWDMVWCLF-UHFFFAOYSA-N methyl(oxo)alumane Chemical compound C[Al]=O CPOFMOWDMVWCLF-UHFFFAOYSA-N 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 238000005086 pumping Methods 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 235000012239 silicon dioxide Nutrition 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 229910052682 stishovite Inorganic materials 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 229910052905 tridymite Inorganic materials 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
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- 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
- 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
- GCBUNTNONFEZPX-UHFFFAOYSA-N 2-methyl-4-naphthalen-1-yl-2,3-dihydroinden-1-one Chemical compound C1=CC=C2C(C3=CC=CC4=C3CC(C4=O)C)=CC=CC2=C1 GCBUNTNONFEZPX-UHFFFAOYSA-N 0.000 description 2
- LPQUJIFWQOFRMH-UHFFFAOYSA-N 2-methyl-4-naphthalen-2-yl-2,3-dihydroinden-1-one Chemical compound C1=CC=CC2=CC(C3=CC=CC4=C3CC(C4=O)C)=CC=C21 LPQUJIFWQOFRMH-UHFFFAOYSA-N 0.000 description 2
- IVYCZGYSZDAEPE-UHFFFAOYSA-N 2-methyl-4-phenyl-2,3-dihydroinden-1-one Chemical compound O=C1C(C)CC2=C1C=CC=C2C1=CC=CC=C1 IVYCZGYSZDAEPE-UHFFFAOYSA-N 0.000 description 2
- JQCCMEDYANGBOG-UHFFFAOYSA-N 2-methyl-7-phenyl-1h-indene Chemical compound C=12CC(C)=CC2=CC=CC=1C1=CC=CC=C1 JQCCMEDYANGBOG-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical class [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 238000003747 Grignard reaction Methods 0.000 description 2
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 239000002253 acid Substances 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- AOJDZKCUAATBGE-UHFFFAOYSA-N bromomethane Chemical compound Br[CH2] AOJDZKCUAATBGE-UHFFFAOYSA-N 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- FOMJJCKPIDFDCV-UHFFFAOYSA-N dimethyl-bis(2-methyl-4-naphthalen-1-yl-1h-inden-1-yl)silane Chemical compound C1=CC=C2C(C3=CC=CC4=C3C=C(C)C4[Si](C)(C)C3C4=C(C(=CC=C4)C=4C5=CC=CC=C5C=CC=4)C=C3C)=CC=CC2=C1 FOMJJCKPIDFDCV-UHFFFAOYSA-N 0.000 description 2
- DIOSZEHGGMTBQZ-UHFFFAOYSA-N dimethyl-bis(2-methyl-4-naphthalen-2-yl-1h-inden-1-yl)silane Chemical compound C1=CC=CC2=CC(C3=CC=CC4=C3C=C(C)C4[Si](C)(C)C3C4=C(C(=CC=C4)C=4C=C5C=CC=CC5=CC=4)C=C3C)=CC=C21 DIOSZEHGGMTBQZ-UHFFFAOYSA-N 0.000 description 2
- OZIJRVRERJTEGQ-UHFFFAOYSA-N dimethyl-bis(2-methyl-4-phenyl-1h-inden-1-yl)silane Chemical compound CC1=CC(C(=CC=C2)C=3C=CC=CC=3)=C2C1[Si](C)(C)C1C(C)=CC2=C1C=CC=C2C1=CC=CC=C1 OZIJRVRERJTEGQ-UHFFFAOYSA-N 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 238000010348 incorporation Methods 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 229920001580 isotactic polymer Polymers 0.000 description 2
- 239000012968 metallocene catalyst Substances 0.000 description 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
- ZBRJXVVKPBZPAN-UHFFFAOYSA-L nickel(2+);triphenylphosphane;dichloride Chemical compound [Cl-].[Cl-].[Ni+2].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 ZBRJXVVKPBZPAN-UHFFFAOYSA-L 0.000 description 2
- 239000002574 poison Substances 0.000 description 2
- 231100000614 poison Toxicity 0.000 description 2
- 230000037048 polymerization activity Effects 0.000 description 2
- 229920000098 polyolefin Polymers 0.000 description 2
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 2
- 229910000105 potassium hydride Inorganic materials 0.000 description 2
- 238000003825 pressing Methods 0.000 description 2
- 230000002040 relaxant effect Effects 0.000 description 2
- 238000007789 sealing Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 229960002317 succinimide Drugs 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- PRBHEGAFLDMLAL-GQCTYLIASA-N (4e)-hexa-1,4-diene Chemical compound C\C=C\CC=C PRBHEGAFLDMLAL-GQCTYLIASA-N 0.000 description 1
- NCMKHUPNOTVWSU-UHFFFAOYSA-N 1-(bromomethyl)-2-phenyl-4-propan-2-ylbenzene Chemical compound CC(C)C1=CC=C(CBr)C(C=2C=CC=CC=2)=C1 NCMKHUPNOTVWSU-UHFFFAOYSA-N 0.000 description 1
- SEXZHJJUKFXNDY-UHFFFAOYSA-N 1-(bromomethyl)-2-phenylbenzene Chemical compound BrCC1=CC=CC=C1C1=CC=CC=C1 SEXZHJJUKFXNDY-UHFFFAOYSA-N 0.000 description 1
- RWZKCIIBYMJJQM-UHFFFAOYSA-N 1-[2-(bromomethyl)-5-propan-2-ylphenyl]naphthalene Chemical compound CC(C)C1=CC=C(CBr)C(C=2C3=CC=CC=C3C=CC=2)=C1 RWZKCIIBYMJJQM-UHFFFAOYSA-N 0.000 description 1
- XSNBKMRTBFQOMX-UHFFFAOYSA-N 1-[2-(bromomethyl)phenyl]-3,5-di(propan-2-yl)benzene Chemical compound CC(C)C1=CC(C(C)C)=CC(C=2C(=CC=CC=2)CBr)=C1 XSNBKMRTBFQOMX-UHFFFAOYSA-N 0.000 description 1
- DLKQHBOKULLWDQ-UHFFFAOYSA-N 1-bromonaphthalene Chemical compound C1=CC=C2C(Br)=CC=CC2=C1 DLKQHBOKULLWDQ-UHFFFAOYSA-N 0.000 description 1
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 1
- APSMUYYLXZULMS-UHFFFAOYSA-N 2-bromonaphthalene Chemical compound C1=CC=CC2=CC(Br)=CC=C21 APSMUYYLXZULMS-UHFFFAOYSA-N 0.000 description 1
- XWPHBDBCETUDSK-UHFFFAOYSA-N 2-methyl-3-(2-phenyl-4-propan-2-ylphenyl)propanoic acid Chemical compound CC(C)C1=CC=C(CC(C)C(O)=O)C(C=2C=CC=CC=2)=C1 XWPHBDBCETUDSK-UHFFFAOYSA-N 0.000 description 1
- FTJPRZYEXZXIBP-UHFFFAOYSA-N 2-methyl-4-naphthalen-1-yl-6-propan-2-yl-2,3-dihydroinden-1-one Chemical compound C1=CC=C2C(C=3C=4CC(C)C(=O)C=4C=C(C=3)C(C)C)=CC=CC2=C1 FTJPRZYEXZXIBP-UHFFFAOYSA-N 0.000 description 1
- OBDQAOAQIAWAJT-UHFFFAOYSA-N 2-methyl-4-phenyl-6-propan-2-yl-2,3-dihydroinden-1-one Chemical compound C=1C(C(C)C)=CC=2C(=O)C(C)CC=2C=1C1=CC=CC=C1 OBDQAOAQIAWAJT-UHFFFAOYSA-N 0.000 description 1
- OCLCRYNZYRSURW-UHFFFAOYSA-N 2-phenyl-2,3-dihydroinden-1-one Chemical class C1C2=CC=CC=C2C(=O)C1C1=CC=CC=C1 OCLCRYNZYRSURW-UHFFFAOYSA-N 0.000 description 1
- KGRICMXGIPJLHQ-UHFFFAOYSA-N 4-[3,5-di(propan-2-yl)phenyl]-2-methyl-2,3-dihydroinden-1-one Chemical compound CC(C)C1=CC(C(C)C)=CC(C=2C=3CC(C)C(=O)C=3C=CC=2)=C1 KGRICMXGIPJLHQ-UHFFFAOYSA-N 0.000 description 1
- UQRONKZLYKUEMO-UHFFFAOYSA-N 4-methyl-1-(2,4,6-trimethylphenyl)pent-4-en-2-one Chemical group CC(=C)CC(=O)Cc1c(C)cc(C)cc1C UQRONKZLYKUEMO-UHFFFAOYSA-N 0.000 description 1
- WOMLTCOPRFPVBR-UHFFFAOYSA-N 7-phenyl-1h-indene Chemical class C=12CC=CC2=CC=CC=1C1=CC=CC=C1 WOMLTCOPRFPVBR-UHFFFAOYSA-N 0.000 description 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
- FAPWLJJCFHVFSJ-UHFFFAOYSA-N 9-[2-(bromomethyl)phenyl]phenanthrene Chemical compound BrCC1=CC=CC=C1C1=CC2=CC=CC=C2C2=CC=CC=C12 FAPWLJJCFHVFSJ-UHFFFAOYSA-N 0.000 description 1
- ONJXMLOOLFUVAT-UHFFFAOYSA-N C(=CC(C)=C)[AlH2] Chemical compound C(=CC(C)=C)[AlH2] ONJXMLOOLFUVAT-UHFFFAOYSA-N 0.000 description 1
- 125000004399 C1-C4 alkenyl group Chemical group 0.000 description 1
- FLFNHHSXSLXYQB-UHFFFAOYSA-L CC1=CC(C(=CC=C2)C=3C=CC=CC=3)=C2C1[Zr](Cl)(Cl)(=[Si](C)C)C1C(C)=CC2=C1C=CC=C2C1=CC=CC=C1 Chemical compound CC1=CC(C(=CC=C2)C=3C=CC=CC=3)=C2C1[Zr](Cl)(Cl)(=[Si](C)C)C1C(C)=CC2=C1C=CC=C2C1=CC=CC=C1 FLFNHHSXSLXYQB-UHFFFAOYSA-L 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 229920000089 Cyclic olefin copolymer Polymers 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 1
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 1
- 229910000799 K alloy Inorganic materials 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical class OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 229910000528 Na alloy Inorganic materials 0.000 description 1
- FIKDKWMGFNSEMI-UHFFFAOYSA-L [Cl-].[Cl-].C1=CC=C2C(C3=CC=CC4=C3C=C(C4[Zr+2])C)=CC=CC2=C1 Chemical compound [Cl-].[Cl-].C1=CC=C2C(C3=CC=CC4=C3C=C(C4[Zr+2])C)=CC=CC2=C1 FIKDKWMGFNSEMI-UHFFFAOYSA-L 0.000 description 1
- QSZGOMRHQRFORD-UHFFFAOYSA-L [Cl-].[Cl-].C=C.C1=CC2=CC=CC=C2C1[Zr+2]C1C2=CC=CC=C2C=C1 Chemical compound [Cl-].[Cl-].C=C.C1=CC2=CC=CC=C2C1[Zr+2]C1C2=CC=CC=C2C=C1 QSZGOMRHQRFORD-UHFFFAOYSA-L 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- JYNZIOFUHBJABQ-UHFFFAOYSA-N allyl-{6-[3-(4-bromo-phenyl)-benzofuran-6-yloxy]-hexyl-}-methyl-amin Chemical group C=1OC2=CC(OCCCCCCN(C)CC=C)=CC=C2C=1C1=CC=C(Br)C=C1 JYNZIOFUHBJABQ-UHFFFAOYSA-N 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- 229920001585 atactic polymer Polymers 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 238000000071 blow moulding Methods 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 239000003426 co-catalyst Substances 0.000 description 1
- 229910000365 copper sulfate Inorganic materials 0.000 description 1
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000006735 deficit Effects 0.000 description 1
- 238000007872 degassing Methods 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000001212 derivatisation Methods 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- LRBPFPZTIZSOGG-UHFFFAOYSA-N dimethyl 2-methylpropanedioate Chemical compound COC(=O)C(C)C(=O)OC LRBPFPZTIZSOGG-UHFFFAOYSA-N 0.000 description 1
- LLMQUBBRGMQZLP-UHFFFAOYSA-N dimethyl-bis(2-methyl-4-phenanthren-9-yl-1h-inden-1-yl)silane Chemical compound C1=CC=C2C(C3=CC=CC4=C3C=C(C)C4[Si](C)(C)C3C4=C(C(=CC=C4)C=4C5=CC=CC=C5C5=CC=CC=C5C=4)C=C3C)=CC3=CC=CC=C3C2=C1 LLMQUBBRGMQZLP-UHFFFAOYSA-N 0.000 description 1
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 1
- GMNSEICSYCVTHZ-UHFFFAOYSA-N dimethylalumanyloxy(dimethyl)alumane Chemical compound C[Al](C)O[Al](C)C GMNSEICSYCVTHZ-UHFFFAOYSA-N 0.000 description 1
- 229910001882 dioxygen Inorganic materials 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- DQYBDCGIPTYXML-UHFFFAOYSA-N ethoxyethane;hydrate Chemical compound O.CCOCC DQYBDCGIPTYXML-UHFFFAOYSA-N 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 229910052731 fluorine Chemical group 0.000 description 1
- 239000011737 fluorine Chemical group 0.000 description 1
- 125000003709 fluoroalkyl group Chemical group 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 1
- 238000012685 gas phase polymerization Methods 0.000 description 1
- 238000005227 gel permeation chromatography Methods 0.000 description 1
- 229910052735 hafnium Inorganic materials 0.000 description 1
- VBJZVLUMGGDVMO-UHFFFAOYSA-N hafnium atom Chemical compound [Hf] VBJZVLUMGGDVMO-UHFFFAOYSA-N 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- LWNVXJAKLXPMAL-UHFFFAOYSA-N hexane tris(2-methylpropyl)alumane Chemical compound C(C(C)C)[Al](CC(C)C)CC(C)C.CCCCCC LWNVXJAKLXPMAL-UHFFFAOYSA-N 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000009434 installation Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 229910001629 magnesium chloride Inorganic materials 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- SJYNFBVQFBRSIB-UHFFFAOYSA-N norbornadiene Chemical compound C1=CC2C=CC1C2 SJYNFBVQFBRSIB-UHFFFAOYSA-N 0.000 description 1
- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 239000002685 polymerization catalyst Substances 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000007873 sieving Methods 0.000 description 1
- 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
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 239000010414 supernatant solution Substances 0.000 description 1
- 238000010557 suspension polymerization reaction Methods 0.000 description 1
- 238000003856 thermoforming Methods 0.000 description 1
- 230000036962 time dependent Effects 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 150000003623 transition metal compounds Chemical class 0.000 description 1
- LFXVBWRMVZPLFK-UHFFFAOYSA-N trioctylalumane Chemical compound CCCCCCCC[Al](CCCCCCCC)CCCCCCCC LFXVBWRMVZPLFK-UHFFFAOYSA-N 0.000 description 1
- 238000013022 venting Methods 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
- 229910052845 zircon Inorganic materials 0.000 description 1
- GFQYVLUOOAAOGM-UHFFFAOYSA-N zirconium(iv) silicate Chemical compound [Zr+4].[O-][Si]([O-])([O-])[O-] GFQYVLUOOAAOGM-UHFFFAOYSA-N 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- 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)
- Food Preservation Except Freezing, Refrigeration, And Drying (AREA)
- Manufacture Of Macromolecular Shaped Articles (AREA)
Priority Applications (16)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19544828A DE19544828A1 (de) | 1995-12-01 | 1995-12-01 | Hochmolekulare Copolymere |
| AT96118856T ATE258940T1 (de) | 1995-12-01 | 1996-11-26 | Hochmolekulare copolymere |
| ES96118856T ES2216031T3 (es) | 1995-12-01 | 1996-11-26 | Copolimeros de elevado peso molecular. |
| AT02019624T ATE456589T1 (de) | 1995-12-01 | 1996-11-26 | Copolymere enthaltend propyleneinheiten und alpha-olefin comonomer |
| DE59611505T DE59611505D1 (de) | 1995-12-01 | 1996-11-26 | Copolymere enthaltend Propyleneinheiten und Alpha-Olefin Comonomer |
| EP96118856A EP0776913B1 (de) | 1995-12-01 | 1996-11-26 | Hochmolekulare Copolymere |
| DE59610907T DE59610907D1 (de) | 1995-12-01 | 1996-11-26 | Hochmolekulare Copolymere |
| EP02019624A EP1270614B1 (de) | 1995-12-01 | 1996-11-26 | Copolymere enthaltend Propyleneinheiten und Alpha-Olefin Comonomer |
| TW085114702A TW454021B (en) | 1995-12-01 | 1996-11-28 | High molecular weight copolymers |
| NO19965106A NO310877B1 (no) | 1995-12-01 | 1996-11-29 | Katalysatorkomponent for fremstilling av en höymolekyl¶r kopolymer, kopolymerer og deres anvendelse |
| CA002191661A CA2191661A1 (en) | 1995-12-01 | 1996-11-29 | High molecular weight copolymers |
| ZA9610051A ZA9610051B (en) | 1995-12-01 | 1996-11-29 | High molecular weight copolymers |
| JP32180896A JP4519952B2 (ja) | 1995-12-01 | 1996-12-02 | 高分子量コポリマー |
| BR9605779A BR9605779A (pt) | 1995-12-01 | 1996-12-02 | Copolímeros de peso molecular elevado |
| US09/058,828 US6057408A (en) | 1995-12-01 | 1998-04-13 | High molecular weight copolymers of propylene and olefins having 2 or 4 to 32 carbon atoms |
| US09/534,588 US6787618B1 (en) | 1995-12-01 | 2000-03-27 | Metallocene compound and high molecular weight copolymers of propylene and olefins having two or four to thirty-two carbon atoms |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19544828A DE19544828A1 (de) | 1995-12-01 | 1995-12-01 | Hochmolekulare Copolymere |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE19544828A1 true DE19544828A1 (de) | 1997-06-05 |
Family
ID=7778922
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19544828A Ceased DE19544828A1 (de) | 1995-12-01 | 1995-12-01 | Hochmolekulare Copolymere |
| DE59611505T Expired - Lifetime DE59611505D1 (de) | 1995-12-01 | 1996-11-26 | Copolymere enthaltend Propyleneinheiten und Alpha-Olefin Comonomer |
| DE59610907T Expired - Lifetime DE59610907D1 (de) | 1995-12-01 | 1996-11-26 | Hochmolekulare Copolymere |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE59611505T Expired - Lifetime DE59611505D1 (de) | 1995-12-01 | 1996-11-26 | Copolymere enthaltend Propyleneinheiten und Alpha-Olefin Comonomer |
| DE59610907T Expired - Lifetime DE59610907D1 (de) | 1995-12-01 | 1996-11-26 | Hochmolekulare Copolymere |
Country Status (11)
| Country | Link |
|---|---|
| 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) |
Families Citing this family (96)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| US6399723B1 (en) | 2000-06-30 | 2002-06-04 | Exxonmobil Chemical Patents Inc. | Metallocene compositions |
| 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 |
| US6870016B1 (en) | 2000-06-30 | 2005-03-22 | Exxonmobil Chemical Patents Inc. | Polymerization process and polymer composition |
| 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 |
| US6380334B1 (en) | 2000-06-30 | 2002-04-30 | Exxonmobil Chemical Patents Inc. | Metallocene compositions |
| JP2003128720A (ja) | 2001-10-19 | 2003-05-08 | Sunallomer Ltd | オレフィン重合用固体助触媒成分、オレフィン重合用触媒およびイオン含有化合物 |
| US20050182266A1 (en) * | 2002-06-12 | 2005-08-18 | Schulte Jorg L. | Transition metal componds their preparation and their use in catalyst systems for the polymerization and copolymerization of olefins |
| US20080153997A1 (en) * | 2006-12-20 | 2008-06-26 | Exxonmobil Research And Engineering | Polymer production at supercritical conditions |
| US8008412B2 (en) * | 2002-09-20 | 2011-08-30 | Exxonmobil Chemical Patents Inc. | Polymer production at supersolution conditions |
| US8058371B2 (en) * | 2002-09-20 | 2011-11-15 | Exxonmobil Chemical Patents Inc. | Super-solution homogeneous propylene polymerization |
| KR100579843B1 (ko) * | 2003-04-01 | 2006-05-12 | 주식회사 엘지화학 | 혼성 담지 메탈로센 촉매 및 그의 제조방법과 이를 이용한폴리올레핀의 제조방법 |
| JP2007505947A (ja) * | 2003-05-28 | 2007-03-15 | バーゼル、ポリオレフィン、ゲゼルシャフト、ミット、ベシュレンクテル、ハフツング | 特定の置換パターンを有する有機遷移金属化合物、ビスシクロペンタジエニル配位子組成物、触媒組成物、及ポリオレフィンの製造法 |
| SA04250253B1 (ar) | 2003-08-21 | 2009-11-10 | استرازينيكا ايه بي | احماض فينوكسي اسيتيك مستبدلة باعتبارها مركبات صيدلانية لعلاج الامراض التنفسية مثل الربو ومرض الانسداد الرئوي المزمن |
| DE10358082A1 (de) | 2003-12-10 | 2005-07-14 | Basell Polyolefine Gmbh | Organübergangsmetallverbindung, Bscyclopentadienyligandsystem, Katalysatorsystem und Hertellung von Polyolefinen |
| ATE445650T1 (de) * | 2004-05-04 | 2009-10-15 | Basell Polyolefine Gmbh | Verfahren zur herstellung von ataktischen 1- butenpolymeren |
| DE602005010255D1 (de) * | 2004-07-08 | 2008-11-20 | Exxonmobil Chem Patents Inc | Katalysator system für die olefinpolymerisation und verfahren zu seiner verwendung |
| GB0418830D0 (en) | 2004-08-24 | 2004-09-22 | Astrazeneca Ab | Novel compounds |
| GB0422057D0 (en) * | 2004-10-05 | 2004-11-03 | Astrazeneca Ab | Novel compounds |
| 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 |
| US7232869B2 (en) * | 2005-05-17 | 2007-06-19 | Novolen Technology Holdings, C.V. | Catalyst composition for olefin polymerization |
| RU2415206C2 (ru) * | 2005-08-19 | 2011-03-27 | Дау Глобал Текнолоджиз, Инк. | Слои из нетканого материала, изготовленного раздувом расплава полимера на основе пропилена, и композитные структуры |
| 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 |
| US7834205B2 (en) | 2006-04-12 | 2010-11-16 | Basell Polyolifine GmbH | Metallocene compounds |
| US8242237B2 (en) | 2006-12-20 | 2012-08-14 | Exxonmobil Chemical Patents Inc. | Phase separator and monomer recycle for supercritical polymerization process |
| US8318875B2 (en) * | 2008-01-18 | 2012-11-27 | Exxonmobil Chemical Patents Inc. | Super-solution homogeneous propylene polymerization and polypropylenes made therefrom |
| ES2424958T3 (es) | 2009-11-13 | 2013-10-10 | Borealis Ag | Proceso para polimerización de olefinas |
| US8603933B2 (en) | 2009-11-13 | 2013-12-10 | Borealis Ag | Process for recovering a transition metal compound |
| WO2011058089A1 (en) | 2009-11-13 | 2011-05-19 | Borealis Ag | Process for producing a polymerization catalyst |
| EP2322568B1 (en) | 2009-11-13 | 2013-05-15 | Borealis AG | Process for producing an olefin polymerization catalyst |
| EP2330136B1 (en) | 2009-12-07 | 2013-08-28 | Borealis AG | Process for the preparation of an unsupported, solid metallocene catalyst system and its use in polymerization of olefins |
| 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 |
| KR101966085B1 (ko) | 2011-07-08 | 2019-04-05 | 보레알리스 아게 | 촉매 |
| US8445620B2 (en) | 2011-08-04 | 2013-05-21 | Exxonmobil Research And Engineering Company | Elastic propylene-alpha-olefin copolymer compositions and processes to produce them |
| 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 |
| EP2745926A1 (en) | 2012-12-21 | 2014-06-25 | Borealis AG | Gas phase polymerization and reactor assembly comprising a fluidized bed reactor and an external moving bed reactor |
| EP2745927A1 (en) | 2012-12-21 | 2014-06-25 | Borealis AG | Fluidized bed reactor with internal moving bed reaction unit |
| ES2645256T3 (es) | 2012-12-21 | 2017-12-04 | Borealis Ag | Catalizadores |
| EP2935296B1 (en) | 2012-12-21 | 2017-11-15 | Borealis AG | Catalyst |
| ES2674576T3 (es) | 2012-12-21 | 2018-07-02 | Borealis Ag | Catalizador |
| EP2759554A1 (en) * | 2013-01-23 | 2014-07-30 | Total Research & Technology Feluy | Process for producing olefin / 3-methyl-1-butene copolymers |
| WO2015009470A1 (en) | 2013-07-17 | 2015-01-22 | Exxonmobil Chemical Patents Inc. | Metallocenes and catalyst compositions derived therefrom |
| US9938364B2 (en) | 2013-07-17 | 2018-04-10 | Exxonmobil Chemical Patents Inc. | Substituted metallocene catalysts |
| SG10201802959WA (en) | 2013-07-17 | 2018-05-30 | Exxonmobil Chemical Patents Inc | Cyclopropyl substituted metallocene catalysts |
| US9644047B2 (en) | 2013-07-17 | 2017-05-09 | Exxonmobil Chemical Patents Inc. | Metallocenes and catalyst compositions derived therefrom |
| US9458260B2 (en) | 2013-07-17 | 2016-10-04 | Exxonmobil Chemical Patents Inc. | Process using substituted metallocene catalysts and products therefrom |
| EP3023450B1 (en) | 2014-11-21 | 2017-07-19 | Borealis AG | Process for producing pellets of soft copolymers |
| EP3124567A1 (en) | 2015-07-30 | 2017-02-01 | Borealis AG | Polypropylene based hot-melt adhesive composition |
| EP3178853B1 (en) | 2015-12-07 | 2018-07-25 | Borealis AG | Process for polymerising alpha-olefin monomers |
| EP3243622B1 (en) | 2016-05-13 | 2020-09-09 | Borealis AG | Process for hydraulic conveying of polyolefin pellets |
| JP7037562B2 (ja) | 2016-11-18 | 2022-03-16 | ボレアリス エージー | 触媒 |
| KR102534541B1 (ko) | 2016-12-15 | 2023-05-18 | 보레알리스 아게 | 고온 용액 중합 공정으로 폴리에틸렌 공중합체를 제조하기 위한 촉매 시스템 |
| CN110337455B (zh) | 2016-12-15 | 2022-05-24 | 博里利斯股份公司 | 在高温溶液聚合法中生产聚乙烯共聚物的新催化剂体系 |
| 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 |
| EP3768735B1 (en) | 2018-03-19 | 2021-12-29 | Borealis AG | Catalysts for olefin polymerization |
| CN112424241B (zh) | 2018-06-28 | 2023-06-06 | 博里利斯股份公司 | 催化剂 |
| 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 |
| EP3887406B1 (en) | 2018-11-30 | 2024-07-17 | Borealis AG | Washing process |
| 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 |
| EP4144435A1 (en) | 2021-09-01 | 2023-03-08 | Borealis AG | Gas phase polymerization process with improved gas recycling |
| EP4389776A1 (en) | 2022-12-20 | 2024-06-26 | Borealis AG | Process |
| EP4389783A1 (en) | 2022-12-20 | 2024-06-26 | Borealis AG | Catalyst transition process |
| EP4638529A1 (en) | 2022-12-23 | 2025-10-29 | Borealis AG | Process for producing a high-flow polypropylene homopolymer |
| WO2024133046A1 (en) | 2022-12-23 | 2024-06-27 | Borealis Ag | Process for producing a polypropylene copolymer |
| EP4638528A1 (en) | 2022-12-23 | 2025-10-29 | Borealis AG | Process for producing a polypropylene homo- or copolymer |
| WO2024240540A1 (en) | 2023-05-23 | 2024-11-28 | Borealis Ag | Process for producing pellets of polyolefins, and pellets so produced |
| WO2025003435A1 (en) | 2023-06-30 | 2025-01-02 | Borealis Ag | Process |
| WO2025219533A1 (en) | 2024-04-18 | 2025-10-23 | Borealis Gmbh | Process for the preparation of a propylene homopolymer |
| WO2025219537A1 (en) | 2024-04-18 | 2025-10-23 | Borealis Gmbh | Process for propylene polymerization with optimized prepolymerization conditions |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0576970A1 (de) * | 1992-06-27 | 1994-01-05 | Hoechst Aktiengesellschaft | Metallocene mit arylsubstituierten Indenylderivaten als Liganden, Verfahren zu ihrer Herstellung und ihre Verwendung als Katalysatoren |
| EP0629632A2 (en) * | 1993-06-07 | 1994-12-21 | Mitsui Petrochemical Industries, Ltd. | Novel transition metal compound for use as a polymerization catalyst |
| DE4333128A1 (de) * | 1993-09-29 | 1995-03-30 | Hoechst Ag | Verfahren zur Herstellung von Polyolefinen |
| EP0646604A1 (de) * | 1993-10-01 | 1995-04-05 | Hoechst Aktiengesellschaft | Verfahren zur Olefinpolymerisation |
| EP0654476A1 (de) * | 1993-11-24 | 1995-05-24 | Hoechst Aktiengesellschaft | Metallocene, Verfahren zu ihrer Herstellung und ihrer Verwendung als Katalysatoren |
| DE4340018A1 (de) * | 1993-11-24 | 1995-06-01 | Hoechst Ag | Metallocene, Verfahren zu ihrer Herstellung und ihre Verwendung als Katalysatoren |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| DE3769528D1 (de) * | 1986-06-30 | 1991-05-29 | Rexene Prod Co | Propylenpolymere und ihre herstellung. |
| CA1327673C (en) * | 1988-06-16 | 1994-03-08 | Sigmund Floyd | Process for production of high molecular weight epdm elastomers using a metallocene-alumoxane catalyst system |
| JP3402473B2 (ja) * | 1991-08-20 | 2003-05-06 | 日本ポリケム株式会社 | オレフィン重合用触媒 |
| EP0584609B1 (de) * | 1992-08-15 | 1999-03-10 | TARGOR GmbH | Verfahren zur Herstellung von Polyolefinen |
| DE69431222T2 (de) * | 1993-06-07 | 2003-04-17 | Mitsui Chemicals, Inc. | Übergangsmetallverbindung, und diese enthaltender Polymerisationkatalysator |
| US5414027A (en) * | 1993-07-15 | 1995-05-09 | Himont Incorporated | High melt strength, propylene polymer, process for making it, and use thereof |
| JP3423378B2 (ja) * | 1993-11-12 | 2003-07-07 | 三井化学株式会社 | 新規な遷移金属化合物および該遷移金属化合物からなるオレフィン重合用触媒成分、該オレフィン重合用触媒成分を含むオレフィン重合用触媒ならびにオレフィンの重合方法 |
| FI945958L (fi) * | 1993-12-21 | 1995-06-22 | Hoechst Ag | Menetelmä polyolefiinien valmistamiseksi |
| DE4344688A1 (de) * | 1993-12-27 | 1995-06-29 | Hoechst Ag | Metallocenverbindung |
| WO1996020225A2 (en) * | 1994-12-20 | 1996-07-04 | Montell Technology Company B.V. | Reactor blend polypropylene, process for the preparation thereof and process for preparing metallocene ligands |
| TW383314B (en) * | 1994-12-20 | 2000-03-01 | Mitsui Petrochemical Ind | Ethylene-alpha-olefin-nonconjugated polyene random copolymer, rubber composition, and process for preparing the random copolymer |
-
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
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0576970A1 (de) * | 1992-06-27 | 1994-01-05 | Hoechst Aktiengesellschaft | Metallocene mit arylsubstituierten Indenylderivaten als Liganden, Verfahren zu ihrer Herstellung und ihre Verwendung als Katalysatoren |
| EP0629632A2 (en) * | 1993-06-07 | 1994-12-21 | Mitsui Petrochemical Industries, Ltd. | Novel transition metal compound for use as a polymerization catalyst |
| DE4333128A1 (de) * | 1993-09-29 | 1995-03-30 | Hoechst Ag | Verfahren zur Herstellung von Polyolefinen |
| EP0646604A1 (de) * | 1993-10-01 | 1995-04-05 | Hoechst Aktiengesellschaft | Verfahren zur Olefinpolymerisation |
| DE4333569A1 (de) * | 1993-10-01 | 1995-04-06 | Hoechst Ag | Verfahren zur Olefinpolymerisation |
| EP0654476A1 (de) * | 1993-11-24 | 1995-05-24 | Hoechst Aktiengesellschaft | Metallocene, Verfahren zu ihrer Herstellung und ihrer Verwendung als Katalysatoren |
| DE4340018A1 (de) * | 1993-11-24 | 1995-06-01 | Hoechst Ag | Metallocene, Verfahren zu ihrer Herstellung und ihre Verwendung als Katalysatoren |
Also Published As
| Publication number | Publication date |
|---|---|
| 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 |
| JP4519952B2 (ja) | 2010-08-04 |
| DE59610907D1 (de) | 2004-03-11 |
| JPH09176222A (ja) | 1997-07-08 |
| US6057408A (en) | 2000-05-02 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0776913B1 (de) | Hochmolekulare Copolymere | |
| EP0576970B1 (de) | Metallocene mit arylsubstituierten Indenylderivaten als Liganden, Verfahren zu ihrer Herstellung und ihre Verwendung als Katalysatoren | |
| DE69617543T3 (de) | Metallocenverbindungen, verfahren zu ihrer herstellung und ihre verwendung in katalysatoren für die olefinpolymerisierung | |
| DE69315471T2 (de) | Katalysator für die Olefinpolymerisation, Verfahren zu seiner Herstellung und seine Verwendung | |
| EP0942938B1 (de) | Geträgertes katalysatorsystem, verfahren zu seiner herstellung und seine verwendung zur polymerisation von olefinen | |
| EP0530647B1 (de) | Metallocene, diese enthaltende Katalysatoren und Verfahren zur Herstellung eines Olefinpolymers unter Verwendung dieser Katalysatoren | |
| EP0659756B1 (de) | Metallocenverbindung | |
| EP0659757B1 (de) | Metallocenverbindung | |
| EP1054911B1 (de) | Katalysatorsystem, verfahren zu seiner herstellung und seine verwendung zur polymerisation von olefinen | |
| EP0661300B1 (de) | Verfahren zur Herstellung von Polyolefinen | |
| DE69631902T2 (de) | Metallocene mit offen-pentodienyl, deren vorläufer und diese enthaltende polymerisationskatalysatoren | |
| EP0654476B1 (de) | Metallocene, Verfahren zu ihrer Herstellung und ihrer Verwendung als Katalysatoren | |
| EP0743317B1 (de) | Metallocene mit einem heterocyclischen Ring und Katalysatoren, die sie enthalten | |
| EP1082363A1 (de) | Organometallverbindung, katalysatorsystem enthaltend diese organometallverbindung und seine verwendung | |
| EP0836608B1 (de) | Metallocene mit silylsubstituierten brücken und deren einsatz für die olefinpolymerisation | |
| EP0984973B1 (de) | Stereorigide metallocenverbindung | |
| EP1000073B1 (de) | Verfahren zur herstellung von metallocenen | |
| EP0557718B1 (de) | Katalysator für die Olefinpolymerisation, Verfahren zu seiner Herstellung und seine Verwendung | |
| EP0749985B1 (de) | Stereorigide Metallocenverbindung | |
| EP1003757B1 (de) | Verfahren zur herstellung von metallocenen | |
| EP0837068A2 (de) | Stereorigide Metallocenverbindung | |
| DE19962905A1 (de) | Übergangsmetallverbindung, Ligandensystem, Katalysatorsystem und seine Verwendung zur Polymerisation und Copolymerisation von Olefinen | |
| EP0868441A2 (de) | Übergangsmetallverbindung | |
| DE19642432A1 (de) | Stereorigide Metallocenverbindung | |
| DE19719104A1 (de) | Stereorigide Metallocenverbindung |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OP8 | Request for examination as to paragraph 44 patent law | ||
| 8127 | New person/name/address of the applicant |
Owner name: TARGOR GMBH, 55116 MAINZ, DE |
|
| 8131 | Rejection |