NO309380B1 - Katalysatorbestanddel og katalysatorer for polymerisering av olefiner, samt fremgangsmåte for polymerisering av olefiner - Google Patents

Katalysatorbestanddel og katalysatorer for polymerisering av olefiner, samt fremgangsmåte for polymerisering av olefiner Download PDF

Info

Publication number: NO309380B1
Authority: NO; Norway
Prior art keywords: bis; methoxymethyl; radicals; equal; carbon atoms
Prior art date: 1995-02-21

Application number

NO960669A

Other languages

English (en)

Norwegian (no)

Other versions

NO960669D0 (no

NO960669L (no

Inventor

Giampiero Morini

Enrico Albizzati

Giulio Balbontin

Giovanni Baruzzi

Antonio Cristofori

Original Assignee

Montell North America Inc

Priority date (The priority date 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 date listed.)

1995-02-21

Filing date

1996-02-20

Publication date

2001-01-22

1995-02-21 Priority claimed from ITMI950317 external-priority patent/IT1274251B/it

1995-02-21 Priority claimed from IT95MI000318 external-priority patent/IT1274252B/it

1996-02-20 Application filed by Montell North America Inc filed Critical Montell North America Inc

1996-02-20 Publication of NO960669D0 publication Critical patent/NO960669D0/no

1996-08-22 Publication of NO960669L publication Critical patent/NO960669L/no

2001-01-22 Publication of NO309380B1 publication Critical patent/NO309380B1/no

Links

239000003054 catalyst Substances 0.000 title claims description 89
238000006116 polymerization reaction Methods 0.000 title claims description 29
150000001336 alkenes Chemical class 0.000 title claims description 26
238000000034 method Methods 0.000 title claims description 17
-1 magnesium halide Chemical class 0.000 claims description 147
150000001875 compounds Chemical class 0.000 claims description 58
239000011949 solid catalyst Substances 0.000 claims description 53
125000004432 carbon atom Chemical group C* 0.000 claims description 48
150000003254 radicals Chemical class 0.000 claims description 43
125000004122 cyclic group Chemical group 0.000 claims description 38
229910052736 halogen Inorganic materials 0.000 claims description 28
XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 claims description 27
229910052739 hydrogen Inorganic materials 0.000 claims description 26
239000001257 hydrogen Substances 0.000 claims description 26
229910003074 TiCl4 Inorganic materials 0.000 claims description 25
125000001424 substituent group Chemical group 0.000 claims description 25
150000002367 halogens Chemical class 0.000 claims description 24
TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 claims description 23
229910052757 nitrogen Inorganic materials 0.000 claims description 23
238000006243 chemical reaction Methods 0.000 claims description 22
125000004433 nitrogen atom Chemical group N* 0.000 claims description 22
125000005842 heteroatom Chemical group 0.000 claims description 21
229910052799 carbon Inorganic materials 0.000 claims description 20
125000003710 aryl alkyl group Chemical group 0.000 claims description 19
125000003118 aryl group Chemical group 0.000 claims description 19
239000011777 magnesium Substances 0.000 claims description 19
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 18
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 18
229910052717 sulfur Inorganic materials 0.000 claims description 18
229910052710 silicon Inorganic materials 0.000 claims description 17
125000000753 cycloalkyl group Chemical group 0.000 claims description 16
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 16
229910052749 magnesium Inorganic materials 0.000 claims description 16
229910052760 oxygen Inorganic materials 0.000 claims description 16
239000000460 chlorine Substances 0.000 claims description 15
229910052801 chlorine Inorganic materials 0.000 claims description 15
229910052731 fluorine Inorganic materials 0.000 claims description 15
239000010936 titanium Substances 0.000 claims description 14
125000000217 alkyl group Chemical group 0.000 claims description 13
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
239000007787 solid Substances 0.000 claims description 12
150000003609 titanium compounds Chemical class 0.000 claims description 11
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 10
239000004215 Carbon black (E152) Substances 0.000 claims description 10
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 10
229930195733 hydrocarbon Natural products 0.000 claims description 10
239000000203 mixture Substances 0.000 claims description 10
150000001721 carbon Chemical group 0.000 claims description 9
239000002904 solvent Substances 0.000 claims description 9
ZWINORFLMHROGF-UHFFFAOYSA-N 9,9-bis(methoxymethyl)fluorene Chemical compound C1=CC=C2C(COC)(COC)C3=CC=CC=C3C2=C1 ZWINORFLMHROGF-UHFFFAOYSA-N 0.000 claims description 8
239000007789 gas Substances 0.000 claims description 8
239000012071 phase Substances 0.000 claims description 8
125000006651 (C3-C20) cycloalkyl group Chemical group 0.000 claims description 7
150000004820 halides Chemical class 0.000 claims description 7
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 6
XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 6
239000007791 liquid phase Substances 0.000 claims description 6
239000001301 oxygen Substances 0.000 claims description 6
229910052698 phosphorus Inorganic materials 0.000 claims description 6
229920006395 saturated elastomer Polymers 0.000 claims description 6
150000005840 aryl radicals Chemical group 0.000 claims description 5
150000002431 hydrogen Chemical class 0.000 claims description 5
125000003367 polycyclic group Chemical group 0.000 claims description 5
125000004434 sulfur atom Chemical group 0.000 claims description 5
RKMGAJGJIURJSJ-UHFFFAOYSA-N 2,2,6,6-tetramethylpiperidine Chemical group CC1(C)CCCC(C)(C)N1 RKMGAJGJIURJSJ-UHFFFAOYSA-N 0.000 claims description 4
150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 4
125000001033 ether group Chemical group 0.000 claims description 4
125000004430 oxygen atom Chemical group O* 0.000 claims description 4
OTIJMHPVYPMCPU-UHFFFAOYSA-N 1,1-bis(methoxymethyl)-2,3-dimethylindene Chemical compound C1=CC=C2C(COC)(COC)C(C)=C(C)C2=C1 OTIJMHPVYPMCPU-UHFFFAOYSA-N 0.000 claims description 3
HHGPZISECHQRLO-UHFFFAOYSA-N 1,1-bis(methoxymethyl)-2-methyl-4-phenylindene Chemical compound COCC1(COC)C(C)=CC2=C1C=CC=C2C1=CC=CC=C1 HHGPZISECHQRLO-UHFFFAOYSA-N 0.000 claims description 3
FXWFWIIEIAUQHQ-UHFFFAOYSA-N 1,1-bis(methoxymethyl)-2-phenylindene Chemical compound C=1C2=CC=CC=C2C(COC)(COC)C=1C1=CC=CC=C1 FXWFWIIEIAUQHQ-UHFFFAOYSA-N 0.000 claims description 3
ZZPVNMUQOQQUHU-UHFFFAOYSA-N 1,1-bis(methoxymethyl)-4,7-dimethylindene Chemical compound CC1=CC=C(C)C2=C1C(COC)(COC)C=C2 ZZPVNMUQOQQUHU-UHFFFAOYSA-N 0.000 claims description 3
JEENAIJBWUBGSW-UHFFFAOYSA-N 1,1-bis(methoxymethyl)-7-(3,3,3-trifluoropropyl)indene Chemical compound C1=CC(CCC(F)(F)F)=C2C(COC)(COC)C=CC2=C1 JEENAIJBWUBGSW-UHFFFAOYSA-N 0.000 claims description 3
ZOIKOBDBSUJRNE-UHFFFAOYSA-N 1,1-bis(methoxymethyl)-7-methylindene Chemical compound C1=CC(C)=C2C(COC)(COC)C=CC2=C1 ZOIKOBDBSUJRNE-UHFFFAOYSA-N 0.000 claims description 3
UQGOQZUZKNXSTQ-UHFFFAOYSA-N 1,1-bis(methoxymethyl)-7-phenylindene Chemical compound C=12C(COC)(COC)C=CC2=CC=CC=1C1=CC=CC=C1 UQGOQZUZKNXSTQ-UHFFFAOYSA-N 0.000 claims description 3
VJTYHGPEEHLNGJ-UHFFFAOYSA-N 1,1-bis(methoxymethyl)-7-propan-2-ylindene Chemical compound C1=CC(C(C)C)=C2C(COC)(COC)C=CC2=C1 VJTYHGPEEHLNGJ-UHFFFAOYSA-N 0.000 claims description 3
ILXXAZBXJLMEQM-UHFFFAOYSA-N 1,1-bis(methoxymethyl)indene Chemical compound C1=CC=C2C(COC)(COC)C=CC2=C1 ILXXAZBXJLMEQM-UHFFFAOYSA-N 0.000 claims description 3
SCTKUNIIBPPKNV-UHFFFAOYSA-N 1,8-dichloro-9,9-bis(methoxymethyl)fluorene Chemical compound C12=CC=CC(Cl)=C2C(COC)(COC)C2=C1C=CC=C2Cl SCTKUNIIBPPKNV-UHFFFAOYSA-N 0.000 claims description 3
PEKQXDFNLCXEIG-UHFFFAOYSA-N 1,8-difluoro-9,9-bis(methoxymethyl)fluorene Chemical compound C12=CC=CC(F)=C2C(COC)(COC)C2=C1C=CC=C2F PEKQXDFNLCXEIG-UHFFFAOYSA-N 0.000 claims description 3
ZFAIPBMPKVESPU-UHFFFAOYSA-N 2,3,4,5,6,7-hexafluoro-9,9-bis(methoxymethyl)fluorene Chemical compound C1=C(F)C(F)=C(F)C2=C1C(COC)(COC)C1=CC(F)=C(F)C(F)=C12 ZFAIPBMPKVESPU-UHFFFAOYSA-N 0.000 claims description 3
LDAYPNRUDRHPCA-UHFFFAOYSA-N 2,7-dicyclopentyl-9,9-bis(methoxymethyl)fluorene Chemical compound C1=C2C(COC)(COC)C3=CC(C4CCCC4)=CC=C3C2=CC=C1C1CCCC1 LDAYPNRUDRHPCA-UHFFFAOYSA-N 0.000 claims description 3
UURZCHPNAPLYER-UHFFFAOYSA-N 4-tert-butyl-9,9-bis(methoxymethyl)fluorene Chemical compound C1=CC=C(C(C)(C)C)C2=C1C(COC)(COC)C1=CC=CC=C12 UURZCHPNAPLYER-UHFFFAOYSA-N 0.000 claims description 3
NUPABKVXQKZAHY-UHFFFAOYSA-N 5,5-bis(methoxymethyl)-1,2,3,4-tetramethylcyclopenta-1,3-diene Chemical compound COCC1(COC)C(C)=C(C)C(C)=C1C NUPABKVXQKZAHY-UHFFFAOYSA-N 0.000 claims description 3
DNQBFNSYXQGWEA-UHFFFAOYSA-N 5,5-bis(methoxymethyl)cyclopenta-1,3-diene Chemical compound COCC1(COC)C=CC=C1 DNQBFNSYXQGWEA-UHFFFAOYSA-N 0.000 claims description 3
TYYSEGNSDSKJDW-UHFFFAOYSA-N 7-cyclohexyl-1,1-bis(methoxymethyl)indene Chemical compound C=12C(COC)(COC)C=CC2=CC=CC=1C1CCCCC1 TYYSEGNSDSKJDW-UHFFFAOYSA-N 0.000 claims description 3
OEGBIJMAWUHNFV-UHFFFAOYSA-N 7-cyclopentyl-1,1-bis(methoxymethyl)indene Chemical compound C=12C(COC)(COC)C=CC2=CC=CC=1C1CCCC1 OEGBIJMAWUHNFV-UHFFFAOYSA-N 0.000 claims description 3
XBHBMIOEDQWGPY-UHFFFAOYSA-N 7-tert-butyl-1,1-bis(methoxymethyl)indene Chemical compound C1=CC(C(C)(C)C)=C2C(COC)(COC)C=CC2=C1 XBHBMIOEDQWGPY-UHFFFAOYSA-N 0.000 claims description 3
UMMOCVFWWKDPNL-UHFFFAOYSA-N 9,9-bis(methoxymethyl)-1,2,3,4,5,6,7,8-octahydrofluorene Chemical compound C1CCCC2=C1C(COC)(COC)C1=C2CCCC1 UMMOCVFWWKDPNL-UHFFFAOYSA-N 0.000 claims description 3
MGQOPBZMDMTUQK-UHFFFAOYSA-N 9,9-bis(methoxymethyl)-1,2,3,4-tetrahydrofluorene Chemical compound C12=CC=CC=C2C(COC)(COC)C2=C1CCCC2 MGQOPBZMDMTUQK-UHFFFAOYSA-N 0.000 claims description 3
BJBJQWLYAGUTIO-UHFFFAOYSA-N 9,9-bis(methoxymethyl)-2,3,6,7-tetramethylfluorene Chemical compound CC1=C(C)C=C2C(COC)(COC)C3=CC(C)=C(C)C=C3C2=C1 BJBJQWLYAGUTIO-UHFFFAOYSA-N 0.000 claims description 3
PQRUIZPAUUOIPY-UHFFFAOYSA-N 9,9-bis(methoxymethyl)-2,7-di(propan-2-yl)fluorene Chemical compound C1=C(C(C)C)C=C2C(COC)(COC)C3=CC(C(C)C)=CC=C3C2=C1 PQRUIZPAUUOIPY-UHFFFAOYSA-N 0.000 claims description 3
UVZNCPVTOYWJAQ-UHFFFAOYSA-N 9,9-bis(methoxymethyl)xanthene Chemical group C1=CC=C2C(COC)(COC)C3=CC=CC=C3OC2=C1 UVZNCPVTOYWJAQ-UHFFFAOYSA-N 0.000 claims description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 3
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
JSDWVMORIKLNNU-UHFFFAOYSA-N [3,3-bis(methoxymethyl)-2,4,5-triphenylcyclopenta-1,4-dien-1-yl]benzene Chemical compound COCC1(COC)C(C=2C=CC=CC=2)=C(C=2C=CC=CC=2)C(C=2C=CC=CC=2)=C1C1=CC=CC=C1 JSDWVMORIKLNNU-UHFFFAOYSA-N 0.000 claims description 3
DFBNDURJLQVNJX-UHFFFAOYSA-N [3,3-bis(methoxymethyl)inden-4-yl]-trimethylsilane Chemical compound C1=CC([Si](C)(C)C)=C2C(COC)(COC)C=CC2=C1 DFBNDURJLQVNJX-UHFFFAOYSA-N 0.000 claims description 3
150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 3
125000004429 atom Chemical group 0.000 claims description 3
150000001993 dienes Chemical class 0.000 claims description 3
150000003377 silicon compounds Chemical class 0.000 claims description 3
239000011593 sulfur Substances 0.000 claims description 3
UFMBYFXYRLFVPN-UHFFFAOYSA-N 1,1-bis[methoxy(phenyl)methyl]indene Chemical compound C1=CC2=CC=CC=C2C1(C(OC)C=1C=CC=CC=1)C(OC)C1=CC=CC=C1 UFMBYFXYRLFVPN-UHFFFAOYSA-N 0.000 claims description 2
POWUJINVZSHIGY-UHFFFAOYSA-N 2,6-di(propan-2-yl)piperidine Chemical group CC(C)C1CCCC(C(C)C)N1 POWUJINVZSHIGY-UHFFFAOYSA-N 0.000 claims description 2
OQYGKBOREGNKLC-UHFFFAOYSA-N 7-tert-butyl-1,1-bis(methoxymethyl)-2-methylindene Chemical compound C1=CC(C(C)(C)C)=C2C(COC)(COC)C(C)=CC2=C1 OQYGKBOREGNKLC-UHFFFAOYSA-N 0.000 claims description 2
MHOBTJZEFPKMLE-UHFFFAOYSA-N 9,9-bis(methoxymethyl)-2,3,6,7-tetramethylxanthene Chemical compound CC1=C(C)C=C2C(COC)(COC)C3=CC(C)=C(C)C=C3OC2=C1 MHOBTJZEFPKMLE-UHFFFAOYSA-N 0.000 claims description 2
QBVOFHFIKBUUMY-UHFFFAOYSA-N 9,9-bis[methoxy(phenyl)methyl]fluorene Chemical compound C12=CC=CC=C2C2=CC=CC=C2C1(C(OC)C=1C=CC=CC=1)C(OC)C1=CC=CC=C1 QBVOFHFIKBUUMY-UHFFFAOYSA-N 0.000 claims description 2
FBGWXZDLLURWAM-UHFFFAOYSA-N 9-(ethoxymethyl)-9-(methoxymethyl)fluorene Chemical compound C1=CC=C2C(COCC)(COC)C3=CC=CC=C3C2=C1 FBGWXZDLLURWAM-UHFFFAOYSA-N 0.000 claims description 2
239000002879 Lewis base Substances 0.000 claims description 2
229910052785 arsenic Inorganic materials 0.000 claims description 2
150000001733 carboxylic acid esters Chemical group 0.000 claims description 2
238000000605 extraction Methods 0.000 claims description 2
150000007527 lewis bases Chemical class 0.000 claims description 2
238000006467 substitution reaction Methods 0.000 claims description 2
229910052718 tin Inorganic materials 0.000 claims description 2
RMXREGKBZYAVSC-UHFFFAOYSA-N 1,1-bis(methoxymethyl)-7-(trifluoromethyl)indene Chemical compound C1=CC(C(F)(F)F)=C2C(COC)(COC)C=CC2=C1 RMXREGKBZYAVSC-UHFFFAOYSA-N 0.000 claims 2
LRFVTYWOQMYALW-UHFFFAOYSA-N 9H-xanthine Chemical compound O=C1NC(=O)NC2=C1NC=N2 LRFVTYWOQMYALW-UHFFFAOYSA-N 0.000 claims 2
125000004965 chloroalkyl group Chemical group 0.000 claims 2
LLVWLCAZSOLOTF-UHFFFAOYSA-N 1-methyl-4-[1,4,4-tris(4-methylphenyl)buta-1,3-dienyl]benzene Chemical compound C1=CC(C)=CC=C1C(C=1C=CC(C)=CC=1)=CC=C(C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 LLVWLCAZSOLOTF-UHFFFAOYSA-N 0.000 claims 1
WFLVIOIMYKVGLP-UHFFFAOYSA-N 9-(methoxymethyl)-9-(pentoxymethyl)fluorene Chemical compound C1=CC=C2C(COCCCCC)(COC)C3=CC=CC=C3C2=C1 WFLVIOIMYKVGLP-UHFFFAOYSA-N 0.000 claims 1
XNGIFLGASWRNHJ-UHFFFAOYSA-N o-dicarboxybenzene Natural products OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 claims 1
229940075420 xanthine Drugs 0.000 claims 1
229920001155 polypropylene Polymers 0.000 description 40
239000004743 Polypropylene Substances 0.000 description 38
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 34
IMNFDUFMRHMDMM-UHFFFAOYSA-N anhydrous n-heptane Natural products CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 20
230000000052 comparative effect Effects 0.000 description 18
229920000642 polymer Polymers 0.000 description 18
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
238000003756 stirring Methods 0.000 description 15
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 14
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 14
229910052782 aluminium Inorganic materials 0.000 description 13
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 13
BHPDSAAGSUWVMP-UHFFFAOYSA-N 3,3-bis(methoxymethyl)-2,6-dimethylheptane Chemical compound COCC(C(C)C)(COC)CCC(C)C BHPDSAAGSUWVMP-UHFFFAOYSA-N 0.000 description 10
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 10
150000002170 ethers Chemical class 0.000 description 9
229910001629 magnesium chloride Inorganic materials 0.000 description 9
239000000047 product Substances 0.000 description 9
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 9
238000001914 filtration Methods 0.000 description 8
150000002430 hydrocarbons Chemical class 0.000 description 8
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VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 7
239000005977 Ethylene Substances 0.000 description 7
239000000178 monomer Substances 0.000 description 7
239000000725 suspension Substances 0.000 description 7
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
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229920001577 copolymer Polymers 0.000 description 6
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 6
230000000694 effects Effects 0.000 description 6
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 6
PVWCLOAAEFMTLH-UHFFFAOYSA-N 4,4-bis(methoxymethyl)-2,6-dimethylheptane Chemical compound COCC(COC)(CC(C)C)CC(C)C PVWCLOAAEFMTLH-UHFFFAOYSA-N 0.000 description 5
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 5
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
239000011737 fluorine Substances 0.000 description 5
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 5
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
UWNADWZGEHDQAB-UHFFFAOYSA-N 2,5-dimethylhexane Chemical group CC(C)CCC(C)C UWNADWZGEHDQAB-UHFFFAOYSA-N 0.000 description 4
MGWAVDBGNNKXQV-UHFFFAOYSA-N diisobutyl phthalate Chemical compound CC(C)COC(=O)C1=CC=CC=C1C(=O)OCC(C)C MGWAVDBGNNKXQV-UHFFFAOYSA-N 0.000 description 4
239000011521 glass Substances 0.000 description 4
238000004519 manufacturing process Methods 0.000 description 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
238000002360 preparation method Methods 0.000 description 4
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
239000012265 solid product Substances 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
HBMODDNTUPGVFW-UHFFFAOYSA-N (1,3-dimethoxy-2-phenylpropan-2-yl)benzene Chemical compound C=1C=CC=CC=1C(COC)(COC)C1=CC=CC=C1 HBMODDNTUPGVFW-UHFFFAOYSA-N 0.000 description 3
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 3
125000004135 2-norbornyl group Chemical group [H]C1([H])C([H])([H])C2([H])C([H])([H])C1([H])C([H])([H])C2([H])* 0.000 description 3
FJZBADSJNSFVDO-UHFFFAOYSA-N 3,3-bis(methoxymethyl)-2,4-dimethylpentane Chemical compound COCC(C(C)C)(C(C)C)COC FJZBADSJNSFVDO-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
229910010062 TiCl3 Inorganic materials 0.000 description 3
230000004888 barrier function Effects 0.000 description 3
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
JWCYDYZLEAQGJJ-UHFFFAOYSA-N dicyclopentyl(dimethoxy)silane Chemical compound C1CCCC1[Si](OC)(OC)C1CCCC1 JWCYDYZLEAQGJJ-UHFFFAOYSA-N 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
125000005843 halogen group Chemical group 0.000 description 3
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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 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical class OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
239000004698 Polyethylene Substances 0.000 description 1
VDZDYDLIDXQASZ-UHFFFAOYSA-N [1-cyclohexyl-3-methoxy-2-(methoxymethyl)propan-2-yl]cyclohexane Chemical compound C1CCCCC1C(COC)(COC)CC1CCCCC1 VDZDYDLIDXQASZ-UHFFFAOYSA-N 0.000 description 1
XMYDKOZNENQEHO-UHFFFAOYSA-N [1-methoxy-2-(methoxymethyl)-3-methylbutan-2-yl]cyclopentane Chemical compound COCC(COC)(C(C)C)C1CCCC1 XMYDKOZNENQEHO-UHFFFAOYSA-N 0.000 description 1
HLXKHZZBHUAIQI-UHFFFAOYSA-N [2,2-bis(methoxymethyl)-3-methylbutyl]cyclohexane Chemical compound COCC(COC)(C(C)C)CC1CCCCC1 HLXKHZZBHUAIQI-UHFFFAOYSA-N 0.000 description 1
ZVGIBQMBZHWERX-UHFFFAOYSA-N [2-(cyclohexylmethyl)-3-methoxy-2-(methoxymethyl)propyl]cyclohexane Chemical compound C1CCCCC1CC(COC)(COC)CC1CCCCC1 ZVGIBQMBZHWERX-UHFFFAOYSA-N 0.000 description 1
RORSEGNGPOMSSV-UHFFFAOYSA-N [3,3-bis(methoxymethyl)-5-phenylpentyl]benzene Chemical compound C=1C=CC=CC=1CCC(COC)(COC)CCC1=CC=CC=C1 RORSEGNGPOMSSV-UHFFFAOYSA-N 0.000 description 1
WVEZHRZEAFZJOI-UHFFFAOYSA-N [3-methoxy-2-(methoxymethyl)-1-phenylpropyl]benzene Chemical compound C=1C=CC=CC=1C(C(COC)COC)C1=CC=CC=C1 WVEZHRZEAFZJOI-UHFFFAOYSA-N 0.000 description 1
ZOUNQYODSPCWEH-UHFFFAOYSA-N [4-methoxy-3-(methoxymethyl)-2-methylbutan-2-yl]benzene Chemical compound COCC(COC)C(C)(C)C1=CC=CC=C1 ZOUNQYODSPCWEH-UHFFFAOYSA-N 0.000 description 1
JXQCBJLNEGKSCN-UHFFFAOYSA-N [4-methoxy-3-(methoxymethyl)butyl]benzene Chemical compound COCC(COC)CCC1=CC=CC=C1 JXQCBJLNEGKSCN-UHFFFAOYSA-N 0.000 description 1
AWLBWJXVYGYRNY-UHFFFAOYSA-N [4-methoxy-3-(methoxymethyl)butyl]cyclohexane Chemical compound COCC(COC)CCC1CCCCC1 AWLBWJXVYGYRNY-UHFFFAOYSA-N 0.000 description 1
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
230000004913 activation Effects 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
230000029936 alkylation Effects 0.000 description 1
238000005804 alkylation reaction Methods 0.000 description 1
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
150000001502 aryl halides Chemical class 0.000 description 1
238000006254 arylation reaction Methods 0.000 description 1
239000002585 base Substances 0.000 description 1
UXXXZMDJQLPQPH-UHFFFAOYSA-N bis(2-methylpropyl) carbonate Chemical compound CC(C)COC(=O)OCC(C)C UXXXZMDJQLPQPH-UHFFFAOYSA-N 0.000 description 1
125000006226 butoxyethyl group Chemical group 0.000 description 1
239000003990 capacitor Substances 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
101150102523 cdc12 gene Proteins 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
229940099352 cholate Drugs 0.000 description 1
ROORDVPLFPIABK-UHFFFAOYSA-N diphenyl carbonate Chemical compound C=1C=CC=CC=1OC(=O)OC1=CC=CC=C1 ROORDVPLFPIABK-UHFFFAOYSA-N 0.000 description 1
DWNAQMUDCDVSLT-UHFFFAOYSA-N diphenyl phthalate Chemical compound C=1C=CC=C(C(=O)OC=2C=CC=CC=2)C=1C(=O)OC1=CC=CC=C1 DWNAQMUDCDVSLT-UHFFFAOYSA-N 0.000 description 1
125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
238000004821 distillation Methods 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
NWPWRAWAUYIELB-UHFFFAOYSA-N ethyl 4-methylbenzoate Chemical compound CCOC(=O)C1=CC=C(C)C=C1 NWPWRAWAUYIELB-UHFFFAOYSA-N 0.000 description 1
YCNSGSUGQPDYTK-UHFFFAOYSA-N ethyl phenyl carbonate Chemical compound CCOC(=O)OC1=CC=CC=C1 YCNSGSUGQPDYTK-UHFFFAOYSA-N 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
238000004817 gas chromatography Methods 0.000 description 1
238000003987 high-resolution gas chromatography Methods 0.000 description 1
238000010813 internal standard method Methods 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
150000002596 lactones Chemical class 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
239000002480 mineral oil Substances 0.000 description 1
235000010446 mineral oil Nutrition 0.000 description 1
TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
239000002245 particle Substances 0.000 description 1
125000004437 phosphorous atom Chemical group 0.000 description 1
125000005936 piperidyl group Chemical group 0.000 description 1
150000004291 polyenes Chemical class 0.000 description 1
229920000570 polyether Polymers 0.000 description 1
229920000573 polyethylene Polymers 0.000 description 1
229920001384 propylene homopolymer Polymers 0.000 description 1
125000000719 pyrrolidinyl group Chemical group 0.000 description 1
238000004445 quantitative analysis Methods 0.000 description 1
238000004062 sedimentation Methods 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
239000005049 silicon tetrachloride Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical group [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
239000012798 spherical particle Substances 0.000 description 1
150000003900 succinic acid esters Chemical class 0.000 description 1
CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 description 1
239000008096 xylene 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
- 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
- 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

Landscapes

Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Materials Engineering (AREA)
Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)

NO960669A 1995-02-21 1996-02-20 Katalysatorbestanddel og katalysatorer for polymerisering av olefiner, samt fremgangsmåte for polymerisering av olefiner NO309380B1 (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
ITMI950317 IT1274251B (it)	1995-02-21	1995-02-21	Componenti e catalizzatori per la polimerizzazione delle olefine
IT95MI000318 IT1274252B (it)	1995-02-21	1995-02-21	Catalizzatori per la polimerizzazione delle olefine

Publications (3)

Publication Number	Publication Date
NO960669D0 NO960669D0 (no)	1996-02-20
NO960669L NO960669L (no)	1996-08-22
NO309380B1 true NO309380B1 (no)	2001-01-22

Family

ID=26331244

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO960669A NO309380B1 (no)	1995-02-21	1996-02-20	Katalysatorbestanddel og katalysatorer for polymerisering av olefiner, samt fremgangsmåte for polymerisering av olefiner

Country Status (19)

Country	Link
EP (1)	EP0728769B1 (2)
JP (1)	JP3904117B2 (2)
KR (1)	KR100424925B1 (2)
CN (1)	CN1090194C (2)
AR (1)	AR000994A1 (2)
AT (1)	ATE169937T1 (2)
AU (1)	AU699522B2 (2)
BR (1)	BR9600767A (2)
CA (1)	CA2169401C (2)
DE (1)	DE69600532T2 (2)
ES (1)	ES2121446T3 (2)
FI (1)	FI119643B (2)
HU (1)	HU221228B1 (2)
IL (1)	IL117114A (2)
IN (1)	IN186169B (2)
MY (1)	MY115716A (2)
NO (1)	NO309380B1 (2)
RU (1)	RU2156260C2 (2)
UA (1)	UA60290C2 (2)

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- 1996-02-20 IN IN316CA1996 patent/IN186169B/en unknown
- 1996-02-21 DE DE69600532T patent/DE69600532T2/de not_active Expired - Lifetime
- 1996-02-21 KR KR1019960004091A patent/KR100424925B1/ko not_active Expired - Fee Related
- 1996-02-21 ES ES96102584T patent/ES2121446T3/es not_active Expired - Lifetime
- 1996-02-21 FI FI960786A patent/FI119643B/fi not_active IP Right Cessation
- 1996-02-21 JP JP03409196A patent/JP3904117B2/ja not_active Expired - Fee Related
- 1996-02-21 AT AT96102584T patent/ATE169937T1/de active
- 1996-02-21 AR ARP960101455A patent/AR000994A1/es unknown
- 1996-02-21 EP EP96102584A patent/EP0728769B1/en not_active Expired - Lifetime

Also Published As

Publication number	Publication date
EP0728769A1 (en)	1996-08-28
ES2121446T3 (es)	1998-11-16
HUP9600390A2 (en)	1997-04-28
RU2156260C2 (ru)	2000-09-20
IL117114A0 (en)	1996-07-23
CA2169401C (en)	2007-04-10
HU221228B1 (en)	2002-08-28
KR100424925B1 (ko)	2004-06-26
HUP9600390A3 (en)	2000-03-28
JPH0920803A (ja)	1997-01-21
HK1010379A1 (en)	1999-06-17
AU4559496A (en)	1996-08-29
CA2169401A1 (en)	1996-08-22
FI119643B (fi)	2009-01-30
MX9600627A (es)	1997-07-31
CN1090194C (zh)	2002-09-04
BR9600767A (pt)	1997-12-23
CN1143651A (zh)	1997-02-26
FI960786L (fi)	1996-08-22
FI960786A0 (fi)	1996-02-21
JP3904117B2 (ja)	2007-04-11
AR000994A1 (es)	1997-08-27
AU699522B2 (en)	1998-12-03
ATE169937T1 (de)	1998-09-15
DE69600532T2 (de)	1999-03-18
MY115716A (en)	2003-08-30
KR960031489A (ko)	1996-09-17
HU9600390D0 (en)	1996-04-29
DE69600532D1 (de)	1998-09-24
UA60290C2 (uk)	2003-10-15
NO960669D0 (no)	1996-02-20
IN186169B (2)	2001-06-30
EP0728769B1 (en)	1998-08-19
IL117114A (en)	2000-02-17
NO960669L (no)	1996-08-22

Legal Events

Date	Code	Title	Description
2010-09-27	MM1K	Lapsed by not paying the annual fees

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