NO311978B1 - Fremgangsmåte for fremstilling av stabiliserte olefinpolymerer - Google Patents
Fremgangsmåte for fremstilling av stabiliserte olefinpolymerer Download PDFInfo
- Publication number
- NO311978B1 NO311978B1 NO19962762A NO962762A NO311978B1 NO 311978 B1 NO311978 B1 NO 311978B1 NO 19962762 A NO19962762 A NO 19962762A NO 962762 A NO962762 A NO 962762A NO 311978 B1 NO311978 B1 NO 311978B1
- Authority
- NO
- Norway
- Prior art keywords
- stands
- alkyl
- formula
- carbon atoms
- group
- Prior art date
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- 238000000034 method Methods 0.000 title claims description 28
- 229920000098 polyolefin Polymers 0.000 title claims description 8
- 230000008569 process Effects 0.000 title claims description 7
- 238000002360 preparation method Methods 0.000 title description 4
- 238000006243 chemical reaction Methods 0.000 claims abstract description 17
- 229920000642 polymer Polymers 0.000 claims abstract description 17
- 150000001412 amines Chemical class 0.000 claims abstract description 14
- 239000012968 metallocene catalyst Substances 0.000 claims abstract description 5
- 230000007704 transition Effects 0.000 claims abstract description 5
- -1 phosphorus(III) compound Chemical class 0.000 claims description 108
- 150000001875 compounds Chemical class 0.000 claims description 74
- 125000004432 carbon atom Chemical group C* 0.000 claims description 60
- 125000000217 alkyl group Chemical group 0.000 claims description 53
- 239000001257 hydrogen Substances 0.000 claims description 48
- 229910052739 hydrogen Inorganic materials 0.000 claims description 48
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 44
- 150000002431 hydrogen Chemical class 0.000 claims description 31
- 229910052751 metal Inorganic materials 0.000 claims description 30
- 239000002184 metal Substances 0.000 claims description 30
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 30
- 238000006116 polymerization reaction Methods 0.000 claims description 21
- 125000001424 substituent group Chemical group 0.000 claims description 19
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 17
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 17
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 16
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 12
- 125000002947 alkylene group Chemical group 0.000 claims description 11
- 238000004519 manufacturing process Methods 0.000 claims description 10
- GDVKFRBCXAPAQJ-UHFFFAOYSA-A dialuminum;hexamagnesium;carbonate;hexadecahydroxide Chemical compound [OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Al+3].[Al+3].[O-]C([O-])=O GDVKFRBCXAPAQJ-UHFFFAOYSA-A 0.000 claims description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- 239000010457 zeolite Substances 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 150000002367 halogens Chemical class 0.000 claims description 8
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 7
- 229910001701 hydrotalcite Inorganic materials 0.000 claims description 7
- 229960001545 hydrotalcite Drugs 0.000 claims description 7
- 239000000344 soap Substances 0.000 claims description 7
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 5
- RKMGAJGJIURJSJ-UHFFFAOYSA-N 2,2,6,6-Tetramethylpiperidine Substances CC1(C)CCCC(C)(C)N1 RKMGAJGJIURJSJ-UHFFFAOYSA-N 0.000 claims description 5
- 229910021536 Zeolite Inorganic materials 0.000 claims description 5
- 150000004649 carbonic acid derivatives Chemical class 0.000 claims description 5
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims description 5
- 229910044991 metal oxide Inorganic materials 0.000 claims description 5
- 150000004706 metal oxides Chemical class 0.000 claims description 5
- 125000001624 naphthyl group Chemical group 0.000 claims description 5
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
- GVJHHUAWPYXKBD-UHFFFAOYSA-N d-alpha-tocopherol Natural products OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 239000011737 fluorine Substances 0.000 claims description 4
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 4
- 230000007306 turnover Effects 0.000 claims description 4
- 125000000732 arylene group Chemical group 0.000 claims description 3
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 3
- 125000006686 (C1-C24) alkyl group Chemical group 0.000 claims description 2
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 2
- LZKGFGLOQNSMBS-UHFFFAOYSA-N 4,5,6-trichlorotriazine Chemical compound ClC1=NN=NC(Cl)=C1Cl LZKGFGLOQNSMBS-UHFFFAOYSA-N 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- 125000004965 chloroalkyl group Chemical group 0.000 claims description 2
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 2
- 229930003799 tocopherol Natural products 0.000 claims description 2
- 235000010384 tocopherol Nutrition 0.000 claims description 2
- 229960001295 tocopherol Drugs 0.000 claims description 2
- 239000011732 tocopherol Substances 0.000 claims description 2
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 claims description 2
- 239000007983 Tris buffer Substances 0.000 claims 1
- 150000001336 alkenes Chemical class 0.000 abstract description 11
- 239000000654 additive Substances 0.000 abstract description 8
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 abstract description 2
- 230000000996 additive effect Effects 0.000 abstract 1
- 208000012839 conversion disease Diseases 0.000 abstract 1
- 150000001450 anions Chemical class 0.000 description 29
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- 239000003054 catalyst Substances 0.000 description 24
- 125000003118 aryl group Chemical group 0.000 description 16
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 16
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
- 239000002253 acid Substances 0.000 description 13
- 125000005843 halogen group Chemical group 0.000 description 13
- 239000000203 mixture Substances 0.000 description 13
- 229910052757 nitrogen Inorganic materials 0.000 description 13
- 229910052726 zirconium Inorganic materials 0.000 description 13
- 239000010936 titanium Substances 0.000 description 12
- 125000001931 aliphatic group Chemical group 0.000 description 11
- 230000000737 periodic effect Effects 0.000 description 11
- 229910052782 aluminium Inorganic materials 0.000 description 10
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 239000003446 ligand Substances 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- 229910052719 titanium Inorganic materials 0.000 description 9
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 8
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 8
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 8
- 125000004429 atom Chemical group 0.000 description 8
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 description 8
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 8
- 150000003839 salts Chemical class 0.000 description 8
- 239000003381 stabilizer Substances 0.000 description 8
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 7
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 7
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 7
- 150000002430 hydrocarbons Chemical class 0.000 description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 7
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 7
- 150000002989 phenols Chemical class 0.000 description 7
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 7
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 6
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 6
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 6
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 6
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- 150000001768 cations Chemical class 0.000 description 6
- 239000011651 chromium Substances 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 239000011777 magnesium Substances 0.000 description 6
- 229910052698 phosphorus Inorganic materials 0.000 description 6
- 239000011148 porous material Substances 0.000 description 6
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 239000002841 Lewis acid Substances 0.000 description 5
- 239000004698 Polyethylene Substances 0.000 description 5
- 229910052804 chromium Inorganic materials 0.000 description 5
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 5
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 5
- 150000007517 lewis acids Chemical class 0.000 description 5
- 229910052718 tin Inorganic materials 0.000 description 5
- FYGHSUNMUKGBRK-UHFFFAOYSA-N 1,2,3-trimethylbenzene Chemical compound CC1=CC=CC(C)=C1C FYGHSUNMUKGBRK-UHFFFAOYSA-N 0.000 description 4
- NQMUGNMMFTYOHK-UHFFFAOYSA-N 1-methoxynaphthalene Chemical compound C1=CC=C2C(OC)=CC=CC2=C1 NQMUGNMMFTYOHK-UHFFFAOYSA-N 0.000 description 4
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 4
- 125000006024 2-pentenyl group Chemical group 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical class P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 4
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 4
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 4
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 4
- 125000003710 aryl alkyl group Chemical group 0.000 description 4
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 239000011575 calcium Substances 0.000 description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 125000004093 cyano group Chemical group *C#N 0.000 description 4
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 4
- 238000000113 differential scanning calorimetry Methods 0.000 description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
- 229910052732 germanium Inorganic materials 0.000 description 4
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 description 4
- 229910052735 hafnium Inorganic materials 0.000 description 4
- VBJZVLUMGGDVMO-UHFFFAOYSA-N hafnium atom Chemical compound [Hf] VBJZVLUMGGDVMO-UHFFFAOYSA-N 0.000 description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- 239000011572 manganese Substances 0.000 description 4
- 150000002739 metals Chemical class 0.000 description 4
- 239000000178 monomer Substances 0.000 description 4
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 4
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 4
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 4
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 4
- 229910052710 silicon Inorganic materials 0.000 description 4
- 239000010703 silicon Substances 0.000 description 4
- 230000006641 stabilisation Effects 0.000 description 4
- 238000011105 stabilization Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 3
- 125000001989 1,3-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([H])C([*:2])=C1[H] 0.000 description 3
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 3
- 125000004825 2,2-dimethylpropylene group Chemical group [H]C([H])([H])C(C([H])([H])[H])(C([H])([H])[*:1])C([H])([H])[*:2] 0.000 description 3
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 3
- 239000005977 Ethylene Substances 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- JKIJEFPNVSHHEI-UHFFFAOYSA-N Phenol, 2,4-bis(1,1-dimethylethyl)-, phosphite (3:1) Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC=C1OP(OC=1C(=CC(=CC=1)C(C)(C)C)C(C)(C)C)OC1=CC=C(C(C)(C)C)C=C1C(C)(C)C JKIJEFPNVSHHEI-UHFFFAOYSA-N 0.000 description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 3
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 3
- 125000004414 alkyl thio group Chemical group 0.000 description 3
- 229910052786 argon Inorganic materials 0.000 description 3
- 239000001273 butane Substances 0.000 description 3
- 125000001589 carboacyl group Chemical group 0.000 description 3
- 239000003638 chemical reducing agent Substances 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 238000007334 copolymerization reaction Methods 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 3
- 125000003709 fluoroalkyl group Chemical group 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 238000005469 granulation Methods 0.000 description 3
- 230000003179 granulation Effects 0.000 description 3
- 125000001072 heteroaryl group Chemical group 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- 239000010955 niobium Substances 0.000 description 3
- 229910052755 nonmetal Inorganic materials 0.000 description 3
- 125000002801 octanoyl group Chemical group C(CCCCCCC)(=O)* 0.000 description 3
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 125000004430 oxygen atom Chemical group O* 0.000 description 3
- XRBCRPZXSCBRTK-UHFFFAOYSA-N phosphonous acid Chemical class OPO XRBCRPZXSCBRTK-UHFFFAOYSA-N 0.000 description 3
- 239000011574 phosphorus Substances 0.000 description 3
- 229910052720 vanadium Inorganic materials 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- 239000011701 zinc Substances 0.000 description 3
- 229910052845 zircon Inorganic materials 0.000 description 3
- GFQYVLUOOAAOGM-UHFFFAOYSA-N zirconium(iv) silicate Chemical compound [Zr+4].[O-][Si]([O-])([O-])[O-] GFQYVLUOOAAOGM-UHFFFAOYSA-N 0.000 description 3
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 description 2
- YAXWOADCWUUUNX-UHFFFAOYSA-N 1,2,2,3-tetramethylpiperidine Chemical class CC1CCCN(C)C1(C)C YAXWOADCWUUUNX-UHFFFAOYSA-N 0.000 description 2
- CRUILBNAQILVHZ-UHFFFAOYSA-N 1,2,3-trimethoxybenzene Chemical compound COC1=CC=CC(OC)=C1OC CRUILBNAQILVHZ-UHFFFAOYSA-N 0.000 description 2
- 125000002030 1,2-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([*:2])C([H])=C1[H] 0.000 description 2
- 125000004958 1,4-naphthylene group Chemical group 0.000 description 2
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 2
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 2
- JTPNRXUCIXHOKM-UHFFFAOYSA-N 1-chloronaphthalene Chemical compound C1=CC=C2C(Cl)=CC=CC2=C1 JTPNRXUCIXHOKM-UHFFFAOYSA-N 0.000 description 2
- XRPKZMVAXPQSCL-UHFFFAOYSA-N 1-cyclopenta-1,3-dien-1-ylethanone Chemical compound CC(=O)C1=CC=CC1 XRPKZMVAXPQSCL-UHFFFAOYSA-N 0.000 description 2
- 125000006017 1-propenyl group Chemical group 0.000 description 2
- KGRVJHAUYBGFFP-UHFFFAOYSA-N 2,2'-Methylenebis(4-methyl-6-tert-butylphenol) Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O KGRVJHAUYBGFFP-UHFFFAOYSA-N 0.000 description 2
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 2
- 125000006040 2-hexenyl group Chemical group 0.000 description 2
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 2
- NPDACUSDTOMAMK-UHFFFAOYSA-N 4-Chlorotoluene Chemical compound CC1=CC=C(Cl)C=C1 NPDACUSDTOMAMK-UHFFFAOYSA-N 0.000 description 2
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- WGKLOLBTFWFKOD-UHFFFAOYSA-N tris(2-nonylphenyl) phosphite Chemical compound CCCCCCCCCC1=CC=CC=C1OP(OC=1C(=CC=CC=1)CCCCCCCCC)OC1=CC=CC=C1CCCCCCCCC WGKLOLBTFWFKOD-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F10/00—Homopolymers and copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
- C08K5/52—Phosphorus bound to oxygen only
- C08K5/527—Cyclic esters
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F4/00—Polymerisation catalysts
- C08F4/42—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors
- C08F4/44—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides
- C08F4/60—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
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F4/00—Polymerisation catalysts
- C08F4/42—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors
- C08F4/44—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides
- C08F4/60—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides together with refractory metals, iron group metals, platinum group metals, manganese, rhenium technetium or compounds thereof
- C08F4/619—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
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F4/00—Polymerisation catalysts
- C08F4/42—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors
- C08F4/44—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides
- C08F4/60—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides together with refractory metals, iron group metals, platinum group metals, manganese, rhenium technetium or compounds thereof
- C08F4/619—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
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
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- C08F4/44—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides
- C08F4/60—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides together with refractory metals, iron group metals, platinum group metals, manganese, rhenium technetium or compounds thereof
- C08F4/62—Refractory metals or compounds thereof
- C08F4/64—Titanium, zirconium, hafnium or compounds thereof
- C08F4/659—Component covered by group C08F4/64 containing a transition metal-carbon bond
- C08F4/6592—Component covered by group C08F4/64 containing a transition metal-carbon bond containing at least one cyclopentadienyl ring, condensed or not, e.g. an indenyl or a fluorenyl ring
- C08F4/65922—Component covered by group C08F4/64 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
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- 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)
- Valve Device For Special Equipments (AREA)
- Electrical Control Of Ignition Timing (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH191295 | 1995-06-29 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO962762D0 NO962762D0 (no) | 1996-06-28 |
| NO962762L NO962762L (no) | 1996-12-30 |
| NO311978B1 true NO311978B1 (no) | 2002-02-25 |
Family
ID=4221505
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO19962762A NO311978B1 (no) | 1995-06-29 | 1996-06-28 | Fremgangsmåte for fremstilling av stabiliserte olefinpolymerer |
Country Status (12)
| Country | Link |
|---|---|
| US (2) | US5703149A (mo) |
| EP (1) | EP0755948B1 (mo) |
| JP (1) | JPH0912621A (mo) |
| KR (1) | KR100420981B1 (mo) |
| AT (1) | ATE202789T1 (mo) |
| BR (1) | BR9602944A (mo) |
| CA (1) | CA2180073A1 (mo) |
| DE (1) | DE59607205D1 (mo) |
| ES (1) | ES2159009T3 (mo) |
| NO (1) | NO311978B1 (mo) |
| TW (1) | TW338046B (mo) |
| ZA (1) | ZA965517B (mo) |
Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6593485B1 (en) | 1994-10-06 | 2003-07-15 | Clariant Finance (Bvi) Limited | Stabilizer composition |
| JP2000517372A (ja) | 1996-09-04 | 2000-12-26 | ザ・ダウ・ケミカル・カンパニー | ポリオレフィン類へのフリーラジカル抑制剤の組み込み |
| CA2237231C (en) | 1998-05-08 | 2006-08-08 | Nova Chemicals Ltd. | Heterogeneous metallocene catalyst |
| NL1012219C2 (nl) * | 1998-06-19 | 2000-04-13 | Ciba Sc Holding Ag | Werkwijze voor de polymersitie van overzadigde polyalkylpiperidinen. |
| IL133922A (en) | 1999-02-01 | 2005-03-20 | Ciba Sc Holding Ag | Compositions comprising polyolefins produced by polymerization over a metallocene catalyst and a stabilizer mixture and a method for stabilizing said polyolefins |
| DE10028432A1 (de) * | 2000-06-13 | 2001-12-20 | Basell Polyolefine Gmbh | Auf calciniertes Hydrotalcit geträgerter Katalysatorfeststoff zur Olefinpolymerisation |
| US6518344B1 (en) * | 2000-08-18 | 2003-02-11 | Ferro Corporation | Flame retarded polyolefin composition |
| ITMI20012085A1 (it) * | 2000-10-17 | 2003-04-09 | Ciba Sc Holding Ag | Polpropilene metallocene stabilizzato |
| GB0111443D0 (en) | 2001-05-10 | 2001-07-04 | Borealis Tech Oy | Olefin polymerisation process |
| US6767937B2 (en) * | 2001-10-03 | 2004-07-27 | Eastman Kodak Company | Stabilizer system for polymer components of displays |
| RU2005106211A (ru) * | 2002-08-07 | 2005-11-20 | Циба Спешиалти Кемикэлз Холдинг Инк. (Ch) | Зародыши бета-кристаллизации как светостабилизирующие агенты для полипропилена |
| JP4866624B2 (ja) * | 2005-03-09 | 2012-02-01 | 日本ポリプロ株式会社 | オレフィン重合用固体触媒成分、オレフィン重合用触媒、およびこれを用いたポリオレフィンの製造方法 |
| JP4969070B2 (ja) * | 2005-03-11 | 2012-07-04 | 株式会社Ａｄｅｋａ | 安定化されたポリマーの製造方法 |
| US20090069171A1 (en) * | 2005-05-12 | 2009-03-12 | Japan Polypropylene Corporation | Catalysts for olefin polymerization, process for production of the catalysts, and method for preservation thereof |
| US20070105992A1 (en) * | 2005-11-07 | 2007-05-10 | Hayder Zahalka | Cycloalkyl phosphites as stabilizers for thermoplastic resins |
| JP5596327B2 (ja) * | 2009-01-28 | 2014-09-24 | 株式会社Ａｄｅｋａ | 食品・医療・水道用パイプ用途のポリオレフィン系樹脂組成物 |
| JP5322681B2 (ja) * | 2009-02-09 | 2013-10-23 | 株式会社Ａｄｅｋａ | 安定化されたポリマーの製造方法 |
| WO2012067017A1 (ja) | 2010-11-16 | 2012-05-24 | 株式会社Adeka | ポリマーの長期安定化方法および不織布、エラストマー組成物の製造方法 |
| EP2682410B1 (en) | 2011-03-02 | 2015-10-07 | Adeka Corporation | Processes of producing laminate film and resin composition for coating members |
| JP2013199551A (ja) | 2012-03-23 | 2013-10-03 | Adeka Corp | 家電材料用及び自動車内装材料用オレフィン樹脂組成物の製造方法 |
| KR102064629B1 (ko) * | 2012-04-27 | 2020-01-08 | 더블유.알. 그레이스 앤드 캄파니-콘. | 활성제 조성물, 이들의 제조, 및 촉매에서 이들의 용도 |
| EP3061788B1 (en) | 2013-10-21 | 2020-08-19 | Adeka Corporation | Method for producing stabilized polymer |
| US10941285B2 (en) | 2017-07-06 | 2021-03-09 | Basf Se | Stabilized polyolefin compositions comprising benzofuranones and acid scavengers |
| WO2020126752A1 (en) * | 2018-12-21 | 2020-06-25 | Basf Se | A polypropylene composition |
| CN111423658A (zh) * | 2020-04-10 | 2020-07-17 | 天津大学 | 一种极性翻转工况下聚丙烯电缆材料及其制备方法、用途 |
| JP7553342B2 (ja) | 2020-12-11 | 2024-09-18 | 日置電機株式会社 | 増幅回路及び測定装置 |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4170589A (en) * | 1978-02-22 | 1979-10-09 | Union Carbide Corporation | Catalytic polymerization of ethylene with supported chromium [II] catalyst in the presence of a phenolic antioxidant |
| AU555386B2 (en) * | 1981-09-24 | 1986-09-25 | Mobil Oil Corp. | Organo-metallic-zeolite catalyst |
| IT1207491B (it) * | 1985-01-30 | 1989-05-25 | Himont Inc | Procedimento per preparare polimeri olefinici, termicamente stabili. |
| US4659685A (en) * | 1986-03-17 | 1987-04-21 | The Dow Chemical Company | Heterogeneous organometallic catalysts containing a supported titanium compound and at least one other supported organometallic compound |
| ES2092913T5 (es) * | 1990-06-22 | 2002-10-16 | Exxonmobil Chem Patents Inc | Catalizadores a base de metaloceno de monociclopentadienilo exento de aluminio para la polimerizacion de olefinas. |
| TW218884B (mo) * | 1991-05-01 | 1994-01-11 | Mitsubishi Kakoki Kk | |
| EP0544308B1 (en) * | 1991-11-28 | 1998-02-18 | Showa Denko Kabushikikaisha | Novel metallocene and process for producing polyolefin using the same |
| MX9207621A (es) * | 1992-01-21 | 1993-07-01 | Ciba Geigy Ag | Nuevos bisfenolfosfitos de cicloalquilideno |
| FI112233B (fi) * | 1992-04-01 | 2003-11-14 | Basell Polyolefine Gmbh | Katalyytti olefiinipolymerointia varten, menetelmä sen valmistamiseksi ja sen käyttö |
| EP0578838A1 (en) * | 1992-04-29 | 1994-01-19 | Hoechst Aktiengesellschaft | Olefin polymerization catalyst, process for its preparation, and its use |
| US5240894A (en) * | 1992-05-18 | 1993-08-31 | Exxon Chemical Patents Inc. | Method for making and using a supported metallocene catalyst system |
| GB2276387B (en) * | 1993-03-25 | 1996-10-02 | Sandoz Ltd | Stabilizing polyolefins with phosphorus compounds |
| CA2126796A1 (en) * | 1993-06-28 | 1994-12-29 | Robert Converse Brade, Iii | Use of lewis bases for activity reduction in metallocene catalyzed olefin polymerization process |
| IT1264946B1 (it) * | 1993-07-16 | 1996-10-17 | Ciba Geigy Spa | Derivati del 2,2,6,6-tetrametil-4-piperidinolo utili come stabilizzanti alla luce ed all'ossidazione per materiali organici. |
| EP0644206B1 (en) * | 1993-09-16 | 1997-12-29 | Showa Denko Kabushiki Kaisha | Olefin polymerization catalyst and process for preparing polyolefin |
| WO1996004318A1 (en) * | 1994-08-05 | 1996-02-15 | Exxon Chemical Patents Inc. | Polymerization catalyst systems, their production and use |
| AU3894395A (en) * | 1994-10-31 | 1996-05-23 | W.R. Grace & Co.-Conn. | Preparation of modified polyolefin catalysts and in situ preparation of supported metallocene and ziegler-natta/metallocene polyolefin catalysts |
-
1996
- 1996-06-13 TW TW085107082A patent/TW338046B/zh active
- 1996-06-18 EP EP96810404A patent/EP0755948B1/de not_active Expired - Lifetime
- 1996-06-18 DE DE59607205T patent/DE59607205D1/de not_active Expired - Fee Related
- 1996-06-18 AT AT96810404T patent/ATE202789T1/de not_active IP Right Cessation
- 1996-06-18 ES ES96810404T patent/ES2159009T3/es not_active Expired - Lifetime
- 1996-06-24 US US08/668,889 patent/US5703149A/en not_active Expired - Fee Related
- 1996-06-27 CA CA002180073A patent/CA2180073A1/en not_active Abandoned
- 1996-06-28 ZA ZA965517A patent/ZA965517B/xx unknown
- 1996-06-28 NO NO19962762A patent/NO311978B1/no not_active IP Right Cessation
- 1996-06-29 KR KR1019960026922A patent/KR100420981B1/ko not_active Expired - Fee Related
- 1996-07-01 JP JP8190104A patent/JPH0912621A/ja not_active Withdrawn
- 1996-07-01 BR BR9602944A patent/BR9602944A/pt not_active IP Right Cessation
-
1997
- 1997-09-10 US US08/929,149 patent/US5955522A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0912621A (ja) | 1997-01-14 |
| US5955522A (en) | 1999-09-21 |
| EP0755948B1 (de) | 2001-07-04 |
| TW338046B (en) | 1998-08-11 |
| EP0755948A3 (de) | 1998-01-07 |
| ATE202789T1 (de) | 2001-07-15 |
| CA2180073A1 (en) | 1996-12-30 |
| KR970001382A (ko) | 1997-01-24 |
| KR100420981B1 (ko) | 2004-07-15 |
| BR9602944A (pt) | 1998-04-28 |
| EP0755948A2 (de) | 1997-01-29 |
| ES2159009T3 (es) | 2001-09-16 |
| US5703149A (en) | 1997-12-30 |
| DE59607205D1 (de) | 2001-08-09 |
| ZA965517B (en) | 1996-12-30 |
| NO962762L (no) | 1996-12-30 |
| NO962762D0 (no) | 1996-06-28 |
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| MM1K | Lapsed by not paying the annual fees |