CA1080208A - Procede pour la polymerisation des olefines - Google Patents
Procede pour la polymerisation des olefinesInfo
- Publication number
- CA1080208A CA1080208A CA249,760A CA249760A CA1080208A CA 1080208 A CA1080208 A CA 1080208A CA 249760 A CA249760 A CA 249760A CA 1080208 A CA1080208 A CA 1080208A
- Authority
- CA
- Canada
- Prior art keywords
- magnesium
- compounds
- titanium
- zirconium
- compound
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 238000000034 method Methods 0.000 title claims abstract description 59
- 238000006116 polymerization reaction Methods 0.000 title claims abstract description 38
- 150000001336 alkenes Chemical class 0.000 title description 3
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 title 1
- 239000010936 titanium Substances 0.000 claims abstract description 102
- 239000011777 magnesium Substances 0.000 claims abstract description 90
- 230000003197 catalytic effect Effects 0.000 claims abstract description 83
- 150000001875 compounds Chemical class 0.000 claims abstract description 80
- 229910052749 magnesium Inorganic materials 0.000 claims abstract description 53
- -1 aluminum halide Chemical class 0.000 claims abstract description 41
- 229910052719 titanium Inorganic materials 0.000 claims abstract description 38
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 35
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims abstract description 33
- 229910052726 zirconium Inorganic materials 0.000 claims abstract description 33
- 239000007787 solid Substances 0.000 claims abstract description 31
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims abstract description 29
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 claims abstract description 27
- 150000002367 halogens Chemical class 0.000 claims abstract description 17
- 150000002902 organometallic compounds Chemical class 0.000 claims abstract description 14
- 229910052782 aluminium Inorganic materials 0.000 claims abstract description 12
- 150000002681 magnesium compounds Chemical class 0.000 claims abstract description 11
- 150000003609 titanium compounds Chemical class 0.000 claims abstract description 7
- 150000003755 zirconium compounds Chemical class 0.000 claims abstract description 6
- 239000004711 α-olefin Substances 0.000 claims abstract description 4
- 239000003153 chemical reaction reagent Substances 0.000 claims description 91
- 229910052751 metal Inorganic materials 0.000 claims description 25
- 239000002184 metal Substances 0.000 claims description 25
- 239000000203 mixture Substances 0.000 claims description 23
- 239000000460 chlorine Substances 0.000 claims description 21
- 125000004432 carbon atom Chemical group C* 0.000 claims description 19
- 229910052760 oxygen Inorganic materials 0.000 claims description 15
- 239000001301 oxygen Substances 0.000 claims description 15
- 238000002360 preparation method Methods 0.000 claims description 14
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 13
- 239000012429 reaction media Substances 0.000 claims description 11
- 229910052801 chlorine Inorganic materials 0.000 claims description 10
- 150000004820 halides Chemical class 0.000 claims description 10
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 9
- 239000005977 Ethylene Substances 0.000 claims description 9
- 239000004215 Carbon black (E152) Substances 0.000 claims description 7
- 229930195733 hydrocarbon Natural products 0.000 claims description 6
- 150000004703 alkoxides Chemical class 0.000 claims description 5
- 238000007334 copolymerization reaction Methods 0.000 claims description 5
- 239000000376 reactant Substances 0.000 claims description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical class [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 230000001747 exhibiting effect Effects 0.000 claims description 4
- 230000000737 periodic effect Effects 0.000 claims description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical class OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 235000011147 magnesium chloride Nutrition 0.000 claims description 3
- DUNKXUFBGCUVQW-UHFFFAOYSA-J zirconium tetrachloride Chemical compound Cl[Zr](Cl)(Cl)Cl DUNKXUFBGCUVQW-UHFFFAOYSA-J 0.000 claims description 3
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims 1
- 238000009826 distribution Methods 0.000 abstract description 12
- 229920000098 polyolefin Polymers 0.000 abstract description 7
- 238000005336 cracking Methods 0.000 abstract description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 33
- 150000003254 radicals Chemical group 0.000 description 26
- 239000004698 Polyethylene Substances 0.000 description 25
- 229920000642 polymer Polymers 0.000 description 18
- 239000003085 diluting agent Substances 0.000 description 15
- 239000001257 hydrogen Substances 0.000 description 15
- 229910052739 hydrogen Inorganic materials 0.000 description 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 14
- 239000007788 liquid Substances 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 9
- 239000000725 suspension Substances 0.000 description 9
- 238000004519 manufacturing process Methods 0.000 description 7
- 229920000573 polyethylene Polymers 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- MCULRUJILOGHCJ-UHFFFAOYSA-N triisobutylaluminium Chemical compound CC(C)C[Al](CC(C)C)CC(C)C MCULRUJILOGHCJ-UHFFFAOYSA-N 0.000 description 7
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 6
- 229920001577 copolymer Polymers 0.000 description 6
- 150000004831 organic oxygen compounds Chemical class 0.000 description 6
- 230000000694 effects Effects 0.000 description 5
- 229910052723 transition metal Inorganic materials 0.000 description 5
- 150000003624 transition metals Chemical class 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 150000001335 aliphatic alkanes Chemical class 0.000 description 4
- 150000001993 dienes Chemical class 0.000 description 4
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 4
- 230000002101 lytic effect Effects 0.000 description 4
- 150000002739 metals Chemical class 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 239000000470 constituent Substances 0.000 description 3
- 150000001924 cycloalkanes Chemical class 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000012190 activator Substances 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 150000001805 chlorine compounds Chemical class 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 230000008030 elimination Effects 0.000 description 2
- 238000003379 elimination reaction Methods 0.000 description 2
- 238000001125 extrusion Methods 0.000 description 2
- 238000010101 extrusion blow moulding Methods 0.000 description 2
- 230000005484 gravity Effects 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 239000001282 iso-butane Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000002798 polar solvent Substances 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 230000001105 regulatory effect Effects 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium(II) oxide Chemical compound [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 2
- RRKODOZNUZCUBN-CCAGOZQPSA-N (1z,3z)-cycloocta-1,3-diene Chemical compound C1CC\C=C/C=C\C1 RRKODOZNUZCUBN-CCAGOZQPSA-N 0.000 description 1
- PRBHEGAFLDMLAL-GQCTYLIASA-N (4e)-hexa-1,4-diene Chemical compound C\C=C\CC=C PRBHEGAFLDMLAL-GQCTYLIASA-N 0.000 description 1
- RYSXWUYLAWPLES-MTOQALJVSA-N (Z)-4-hydroxypent-3-en-2-one titanium Chemical compound [Ti].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O RYSXWUYLAWPLES-MTOQALJVSA-N 0.000 description 1
- PTPLXVHPKMTVIW-FPLPWBNLSA-N (Z)-hydroxyimino-oxido-phenylazanium Chemical class O\N=[N+](/[O-])c1ccccc1 PTPLXVHPKMTVIW-FPLPWBNLSA-N 0.000 description 1
- YOBOXHGSEJBUPB-MTOQALJVSA-N (z)-4-hydroxypent-3-en-2-one;zirconium Chemical compound [Zr].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O YOBOXHGSEJBUPB-MTOQALJVSA-N 0.000 description 1
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 1
- PEIHRCIDUUJQCQ-UHFFFAOYSA-N 1,3-bis(ethenyl)cyclohexane Chemical compound C=CC1CCCC(C=C)C1 PEIHRCIDUUJQCQ-UHFFFAOYSA-N 0.000 description 1
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-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
- ISPYQTSUDJAMAB-UHFFFAOYSA-N 2-chlorophenol Chemical class OC1=CC=CC=C1Cl ISPYQTSUDJAMAB-UHFFFAOYSA-N 0.000 description 1
- NEAQRZUHTPSBBM-UHFFFAOYSA-N 2-hydroxy-3,3-dimethyl-7-nitro-4h-isoquinolin-1-one Chemical class C1=C([N+]([O-])=O)C=C2C(=O)N(O)C(C)(C)CC2=C1 NEAQRZUHTPSBBM-UHFFFAOYSA-N 0.000 description 1
- BBDKZWKEPDTENS-UHFFFAOYSA-N 4-Vinylcyclohexene Chemical compound C=CC1CCC=CC1 BBDKZWKEPDTENS-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- 229910000951 Aluminide Inorganic materials 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
- 241001212789 Dynamis Species 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- MUQNGPZZQDCDFT-JNQJZLCISA-N Halcinonide Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H]3OC(C)(C)O[C@@]3(C(=O)CCl)[C@@]1(C)C[C@@H]2O MUQNGPZZQDCDFT-JNQJZLCISA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 241001676573 Minium Species 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 229910010066 TiC14 Inorganic materials 0.000 description 1
- 229910003074 TiCl4 Inorganic materials 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 229910007932 ZrCl4 Inorganic materials 0.000 description 1
- 229910007998 ZrF4 Inorganic materials 0.000 description 1
- IPBVNPXQWQGGJP-UHFFFAOYSA-N acetic acid phenyl ester Natural products CC(=O)OC1=CC=CC=C1 IPBVNPXQWQGGJP-UHFFFAOYSA-N 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- WNLRTRBMVRJNCN-UHFFFAOYSA-L adipate(2-) Chemical compound [O-]C(=O)CCCCC([O-])=O WNLRTRBMVRJNCN-UHFFFAOYSA-L 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 150000001350 alkyl halides Chemical class 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
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- YHWCPXVTRSHPNY-UHFFFAOYSA-N butan-1-olate;titanium(4+) Chemical compound [Ti+4].CCCC[O-].CCCC[O-].CCCC[O-].CCCC[O-] YHWCPXVTRSHPNY-UHFFFAOYSA-N 0.000 description 1
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 1
- 229910052793 cadmium Inorganic materials 0.000 description 1
- 238000003490 calendering Methods 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000009918 complex formation Effects 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- XHOBAHOLCPTDRT-UHFFFAOYSA-N cyclohexanolate Chemical compound [O-]C1CCCCC1 XHOBAHOLCPTDRT-UHFFFAOYSA-N 0.000 description 1
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 1
- YNLAOSYQHBDIKW-UHFFFAOYSA-M diethylaluminium chloride Chemical compound CC[Al](Cl)CC YNLAOSYQHBDIKW-UHFFFAOYSA-M 0.000 description 1
- HQWPLXHWEZZGKY-UHFFFAOYSA-N diethylzinc Chemical compound CC[Zn]CC HQWPLXHWEZZGKY-UHFFFAOYSA-N 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- MGDOJPNDRJNJBK-UHFFFAOYSA-N ethylaluminum Chemical compound [Al].C[CH2] MGDOJPNDRJNJBK-UHFFFAOYSA-N 0.000 description 1
- UAIZDWNSWGTKFZ-UHFFFAOYSA-L ethylaluminum(2+);dichloride Chemical compound CC[Al](Cl)Cl UAIZDWNSWGTKFZ-UHFFFAOYSA-L 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229940028332 halog Drugs 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 229920001903 high density polyethylene Polymers 0.000 description 1
- 238000000265 homogenisation Methods 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- TUJKJAMUKRIRHC-UHFFFAOYSA-N hydroxyl Chemical compound [OH] TUJKJAMUKRIRHC-UHFFFAOYSA-N 0.000 description 1
- 150000002443 hydroxylamines Chemical class 0.000 description 1
- UWNADWZGEHDQAB-UHFFFAOYSA-N i-Pr2C2H4i-Pr2 Natural products CC(C)CCC(C)C UWNADWZGEHDQAB-UHFFFAOYSA-N 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229910001629 magnesium chloride Inorganic materials 0.000 description 1
- DLPASUVGCQPFFO-UHFFFAOYSA-N magnesium;ethane Chemical compound [Mg+2].[CH2-]C.[CH2-]C DLPASUVGCQPFFO-UHFFFAOYSA-N 0.000 description 1
- XDKQUSKHRIUJEO-UHFFFAOYSA-N magnesium;ethanolate Chemical compound [Mg+2].CC[O-].CC[O-] XDKQUSKHRIUJEO-UHFFFAOYSA-N 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 125000005609 naphthenate group Chemical group 0.000 description 1
- 101150006061 neur gene Proteins 0.000 description 1
- 229910017464 nitrogen compound Inorganic materials 0.000 description 1
- SJYNFBVQFBRSIB-UHFFFAOYSA-N norbornadiene Chemical compound C1=CC2C=CC1C2 SJYNFBVQFBRSIB-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- 229940049964 oleate Drugs 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 150000002927 oxygen compounds Chemical class 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 239000002530 phenolic antioxidant Substances 0.000 description 1
- 229940049953 phenylacetate Drugs 0.000 description 1
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000000135 prohibitive effect Effects 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- LMHHRCOWPQNFTF-UHFFFAOYSA-N s-propan-2-yl azepane-1-carbothioate Chemical compound CC(C)SC(=O)N1CCCCCC1 LMHHRCOWPQNFTF-UHFFFAOYSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229940116351 sebacate Drugs 0.000 description 1
- CXMXRPHRNRROMY-UHFFFAOYSA-L sebacate(2-) Chemical compound [O-]C(=O)CCCCCCCCC([O-])=O CXMXRPHRNRROMY-UHFFFAOYSA-L 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 238000010408 sweeping Methods 0.000 description 1
- AFCAKJKUYFLYFK-UHFFFAOYSA-N tetrabutyltin Chemical compound CCCC[Sn](CCCC)(CCCC)CCCC AFCAKJKUYFLYFK-UHFFFAOYSA-N 0.000 description 1
- RWWNQEOPUOCKGR-UHFFFAOYSA-N tetraethyltin Chemical compound CC[Sn](CC)(CC)CC RWWNQEOPUOCKGR-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- UBZYKBZMAMTNKW-UHFFFAOYSA-J titanium tetrabromide Chemical compound Br[Ti](Br)(Br)Br UBZYKBZMAMTNKW-UHFFFAOYSA-J 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 150000003623 transition metal compounds Chemical class 0.000 description 1
- SQBBHCOIQXKPHL-UHFFFAOYSA-N tributylalumane Chemical compound CCCC[Al](CCCC)CCCC SQBBHCOIQXKPHL-UHFFFAOYSA-N 0.000 description 1
- VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 description 1
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 1
- UKHQRARQNZOXRL-UHFFFAOYSA-N trimethyltin Chemical compound C[SnH](C)C UKHQRARQNZOXRL-UHFFFAOYSA-N 0.000 description 1
- NLSXASIDNWDYMI-UHFFFAOYSA-N triphenylsilanol Chemical compound C=1C=CC=CC=1[Si](C=1C=CC=CC=1)(O)C1=CC=CC=C1 NLSXASIDNWDYMI-UHFFFAOYSA-N 0.000 description 1
- USJZIJNMRRNDPO-UHFFFAOYSA-N tris-decylalumane Chemical compound CCCCCCCCCC[Al](CCCCCCCCCC)CCCCCCCCCC USJZIJNMRRNDPO-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- OMQSJNWFFJOIMO-UHFFFAOYSA-J zirconium tetrafluoride Chemical compound F[Zr](F)(F)F OMQSJNWFFJOIMO-UHFFFAOYSA-J 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
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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| LU72278A LU72278A1 (en, 2012) | 1975-04-14 | 1975-04-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1080208A true CA1080208A (fr) | 1980-06-24 |
Family
ID=19727905
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA249,760A Expired CA1080208A (fr) | 1975-04-14 | 1976-04-07 | Procede pour la polymerisation des olefines |
Country Status (27)
| Country | Link |
|---|---|
| US (1) | US4109071A (en, 2012) |
| JP (2) | JPS51138785A (en, 2012) |
| AR (1) | AR207281A1 (en, 2012) |
| AT (1) | AT347677B (en, 2012) |
| BE (1) | BE840378A (en, 2012) |
| BR (1) | BR7602156A (en, 2012) |
| CA (1) | CA1080208A (en, 2012) |
| CH (1) | CH617212A5 (en, 2012) |
| DD (1) | DD126387A5 (en, 2012) |
| DE (1) | DE2615390C3 (en, 2012) |
| DK (1) | DK149864C (en, 2012) |
| ES (1) | ES446816A1 (en, 2012) |
| FI (1) | FI61494C (en, 2012) |
| FR (1) | FR2307824A1 (en, 2012) |
| GB (1) | GB1490509A (en, 2012) |
| GR (1) | GR58454B (en, 2012) |
| IN (1) | IN143034B (en, 2012) |
| IT (1) | IT1059283B (en, 2012) |
| LU (1) | LU72278A1 (en, 2012) |
| MX (1) | MX3477E (en, 2012) |
| NL (1) | NL164569C (en, 2012) |
| NO (1) | NO146991C (en, 2012) |
| PT (1) | PT64985B (en, 2012) |
| SE (1) | SE430253B (en, 2012) |
| SU (1) | SU795488A3 (en, 2012) |
| TR (1) | TR19292A (en, 2012) |
| ZA (1) | ZA762076B (en, 2012) |
Families Citing this family (59)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| LU77489A1 (en, 2012) * | 1977-06-06 | 1979-01-19 | ||
| JPS54112982A (en) * | 1978-02-02 | 1979-09-04 | Sumitomo Chem Co Ltd | Polymerization of olefins |
| US4258167A (en) * | 1978-02-13 | 1981-03-24 | Nissan Chemical Industries, Ltd. | Process for producing powdery isotactic polyolefin |
| US4226964A (en) * | 1978-02-23 | 1980-10-07 | Mitsubishi Chemical Industries Ltd. | Process for polymerizing olefin |
| US4260723A (en) * | 1978-06-27 | 1981-04-07 | Chisso Corporation | Method for producing olefin polymers |
| US4210559A (en) * | 1978-10-30 | 1980-07-01 | Standard Oil Company (Indiana) | Catalyst for the preparation of polyalpha-olefins having broad molecular weight distributions |
| JPS5919567B2 (ja) * | 1978-11-27 | 1984-05-07 | 昭和電工株式会社 | 改善されたエチレン系重合体の製造方法 |
| US4233182A (en) * | 1978-12-26 | 1980-11-11 | Standard Oil Company (Indiana) | High activity catalyst for the polymerization of alpha-olefins |
| WO1980001485A1 (en) * | 1979-01-18 | 1980-07-24 | Mitsubishi Chem Ind | Process for producing olefin polymer |
| US4363746A (en) | 1979-05-29 | 1982-12-14 | Phillips Petroleum Company | Composition of matter and method of preparing same, catalyst, method of producing the catalyst and polymerization process employing the catalyst |
| JPS55160002A (en) * | 1979-06-01 | 1980-12-12 | Chisso Corp | Production of olefin polymer |
| US4366298A (en) * | 1979-07-05 | 1982-12-28 | Wacker-Chemie Gmbh | Process and heavy metal catalyst for the polymerization of α-olefins, particularly polyethylene |
| JPS6024805B2 (ja) * | 1979-09-05 | 1985-06-14 | 日石三菱株式会社 | 共重合体の製法 |
| US4269733A (en) * | 1979-09-28 | 1981-05-26 | The Dow Chemical Company | Ultra high efficiency catalyst for polymerizing olefins |
| US4363902A (en) * | 1980-03-17 | 1982-12-14 | Wacker-Chemie Gmbh | Process and heavy metal catalyst for the polymerization of α-olefins, particularly polyethylene |
| US4384087A (en) * | 1980-03-24 | 1983-05-17 | Phillips Petroleum Company | Composition of matter and method of preparing same, catalyst, method of producing the catalyst and polymerization process employing the catalyst |
| DE3171693D1 (en) * | 1980-06-25 | 1985-09-12 | Idemitsu Kosan Co | Process for the production of polyethylene |
| JPS5712007A (en) * | 1980-06-27 | 1982-01-21 | Idemitsu Kosan Co Ltd | Production of polyethylene |
| DE3025760A1 (de) * | 1980-07-08 | 1982-02-04 | Wacker-Chemie GmbH, 8000 München | Verfahren zur polymersation von (alpha) -olefinen |
| US4326988A (en) * | 1980-08-12 | 1982-04-27 | Phillips Petroleum Company | Catalyst, method of producing the catalyst, and polymerization process employing the catalyst |
| US4325837A (en) * | 1980-08-12 | 1982-04-20 | Phillips Petroleum Company | Catalyst, method of producing the catalyst, and polymerization process employing the catalyst |
| US4356111A (en) * | 1980-10-20 | 1982-10-26 | The Dow Chemical Company | High efficiency catalyst containing titanium and zirconium for polymerizing olefins |
| US4310648A (en) * | 1980-10-20 | 1982-01-12 | The Dow Chemical Company | Polymerization of olefins in the presence of a catalyst containing titanium and zirconium |
| US4399053A (en) * | 1980-12-24 | 1983-08-16 | The Dow Chemical Company | High efficiency catalyst containing titanium, zirconium and zinc for polymerizing olefins |
| US4525554A (en) * | 1981-03-04 | 1985-06-25 | Mitsubishi Chemical Industries Ltd. | Process for polymerizing olefin |
| US4394291A (en) * | 1981-03-04 | 1983-07-19 | Phillips Petroleum Company | Polyolefin polymerization process and catalyst |
| US4396747A (en) * | 1981-05-22 | 1983-08-02 | Phillips Petroleum Company | Zirconium-titanium catalyzed olefin polymerization |
| US4472523A (en) * | 1981-05-22 | 1984-09-18 | Phillips Petroleum Company | Zirconium-titanium catalyzed olefin polymerization |
| US4376065A (en) * | 1981-06-01 | 1983-03-08 | The Dow Chemical Company | Organo zirconium-chromium compound, catalyst prepared therefrom and polymerization of olefins therewith |
| US4361685A (en) * | 1981-06-01 | 1982-11-30 | The Dow Chemical Company | Polymerization of olefins in the presence of catalyst prepared from organo zirconium-chromium mixtures |
| US4518751A (en) * | 1981-06-05 | 1985-05-21 | Idemitsu Kosan Company Limited | Process for the production of polyethylene |
| US4381253A (en) * | 1981-10-22 | 1983-04-26 | The Dow Chemical Company | Ultra high efficiency catalyst for polymerizing olefins |
| US4409126A (en) * | 1981-10-22 | 1983-10-11 | The Dow Chemical Company | Ultra high efficiency catalyst for polymerizing olefins |
| US4380508A (en) * | 1981-10-22 | 1983-04-19 | The Dow Chemical Company | Ultra high efficiency catalyst for polymerizing olefins |
| US4379760A (en) * | 1981-11-12 | 1983-04-12 | The Dow Chemical Company | High efficiency catalyst for polymerizing olefins |
| EP0083671A1 (en) * | 1982-01-07 | 1983-07-20 | The Dow Chemical Company | High efficiency catalyst containing titanium and zirconium and process for polymerizing olefins |
| US4497906A (en) * | 1982-02-16 | 1985-02-05 | Sumitomo Chemical Company, Limited | Solid catalyst component for olefin polymerization |
| US4550094A (en) * | 1982-02-16 | 1985-10-29 | Sumitomo Chemical Company, Limited | Solid catalyst component for olefin polymerization |
| US4675368A (en) * | 1982-10-04 | 1987-06-23 | Solvay & Cie. | Process for inhibiting crust formation in reactors during alpha-olefin prepolymerization modification of Ziegler catalyst |
| US4587727A (en) * | 1983-07-05 | 1986-05-13 | International Business Machines Corporation | System for generating circuit boards using electroeroded sheet layers |
| JPS6042404A (ja) * | 1983-08-16 | 1985-03-06 | Sumitomo Chem Co Ltd | オレフインの重合方法 |
| IT1212779B (it) * | 1983-10-14 | 1989-11-30 | Enichimica Secondaria | Procedimento per la polimerizzazione di etilene e per la copolimerizzazione di etilene con alfa-olefine e catalizzatore relativo. |
| US4496661A (en) * | 1983-10-24 | 1985-01-29 | The Dow Chemical Company | High efficiency catalyst for polymerizing olefins |
| US4618660A (en) * | 1984-06-29 | 1986-10-21 | Exxon Research & Engineering Co. | Polymerization catalyst |
| US5064797A (en) * | 1987-04-03 | 1991-11-12 | Phillips Petroleum Company | Process for producing polyolefins and polyolefin catalysts |
| US4939217A (en) * | 1987-04-03 | 1990-07-03 | Phillips Petroleum Company | Process for producing polyolefins and polyolefin catalysts |
| JPH0725827B2 (ja) * | 1987-06-02 | 1995-03-22 | 出光石油化学株式会社 | エチレン重合体の製造方法 |
| EP0522424B1 (en) * | 1991-07-03 | 1996-12-18 | Tosoh Corporation | Method for producing a polyolefin |
| US5332707A (en) * | 1992-07-31 | 1994-07-26 | Amoco Corporation | Olefin polymerization and copolymerization catalyst |
| US5374597A (en) * | 1993-02-12 | 1994-12-20 | Quantum Chemical Corporation | Vanadium based olefin polymerization catalyst |
| US5399540A (en) * | 1993-02-12 | 1995-03-21 | Quantum Chemical Corporation | ZR/V multi-site olefin polymerization catalyst |
| US5405817A (en) * | 1993-02-12 | 1995-04-11 | Quantum Chemical Corporation | V/TI multi-site olefin polymerization catalyst |
| BE1009308A3 (fr) * | 1995-04-28 | 1997-02-04 | Solvay | Polymere d'ethylene et procedes pour son obtention. |
| AU5900000A (en) * | 1999-06-30 | 2001-01-31 | Union Carbide Chemicals & Plastics Technology Corporation | Magnesium-zirconium alkoxide complexes and polymerization catalysts made therefrom |
| AR025187A1 (es) | 1999-06-30 | 2002-11-13 | Poration Union Carbide Chemicals & Plastics Technology Cor | Un precursor de complejo de metales mixtos, un metodo para elaborarlo, un procatalizador de la polimerizacion preparado mediante la halogenacion delprecursor y un metodo para polimerizar una olefina |
| US20090048402A1 (en) * | 2007-08-17 | 2009-02-19 | Lynch Michael W | Preparing multimodal polyethylene having controlled long chain branching distribution |
| US8809220B2 (en) * | 2010-04-13 | 2014-08-19 | Union Carbide Chemicals & Plastics Technology Llc | Method of making Ziegler-Natta type catalysts |
| US20250109218A1 (en) | 2023-09-29 | 2025-04-03 | Formosa Plastics Corporation, U.S.A. | Method for preparing catalyst component for polymerization of polyolefin without the use of internal electron donors |
| US20250115687A1 (en) | 2023-10-06 | 2025-04-10 | Formosa Plastics Corporation, U.S.A. | Production method for solid catalyst component for polymerizing olefins, and catalyst for polymerizaing olefins |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL213149A (en, 2012) * | 1955-12-22 | |||
| FR2093306A6 (fr) | 1970-06-09 | 1972-01-28 | Solvay | Catalyseurs et procede perfectionnes pour la polymerisation et la copolymerisation des olefines |
| US3678025A (en) * | 1970-05-22 | 1972-07-18 | Dow Chemical Co | Preparation of linear alpha olefin polymers having broad molecular weight distributions |
| DE2128760A1 (de) * | 1970-06-12 | 1971-12-16 | Shell Int Research | Verfahren zur Polymerisation von Olefinen |
| BE791676A (fr) * | 1971-12-08 | 1973-05-21 | Solvay | Procédé pour la polymérisation des oléfines |
| LU65587A1 (en, 2012) | 1972-06-22 | 1973-12-27 | ||
| IT1020055B (it) * | 1973-09-08 | 1977-12-20 | Solvay | Polimerizzazione a bassa pressio ne di olefine |
| JPS5146387A (en) * | 1974-10-18 | 1976-04-20 | Yozo Kondo | Horiorefuinno seizohoho |
| US3939137A (en) * | 1974-11-22 | 1976-02-17 | Phillips Petroleum Company | Silane adjuvant for chromium oxide catalyst |
-
1975
- 1975-04-14 LU LU72278A patent/LU72278A1/xx unknown
-
1976
- 1976-01-01 AR AR262871A patent/AR207281A1/es active
- 1976-03-26 FR FR7609251A patent/FR2307824A1/fr active Granted
- 1976-04-05 BE BE165842A patent/BE840378A/xx not_active IP Right Cessation
- 1976-04-05 IT IT21940/76A patent/IT1059283B/it active
- 1976-04-07 CA CA249,760A patent/CA1080208A/fr not_active Expired
- 1976-04-07 ZA ZA762076A patent/ZA762076B/xx unknown
- 1976-04-08 CH CH447576A patent/CH617212A5/fr not_active IP Right Cessation
- 1976-04-08 ES ES446816A patent/ES446816A1/es not_active Expired
- 1976-04-08 IN IN616/CAL/76A patent/IN143034B/en unknown
- 1976-04-08 PT PT64985A patent/PT64985B/pt unknown
- 1976-04-08 GR GR50506A patent/GR58454B/el unknown
- 1976-04-08 BR BR760215,A patent/BR7602156A/pt unknown
- 1976-04-08 DE DE2615390A patent/DE2615390C3/de not_active Expired
- 1976-04-09 NO NO761239A patent/NO146991C/no unknown
- 1976-04-09 TR TR19292A patent/TR19292A/xx unknown
- 1976-04-09 DD DD192293A patent/DD126387A5/xx unknown
- 1976-04-09 MX MX000163U patent/MX3477E/es unknown
- 1976-04-09 US US05/675,320 patent/US4109071A/en not_active Expired - Lifetime
- 1976-04-12 JP JP51041174A patent/JPS51138785A/ja active Granted
- 1976-04-12 AT AT265676A patent/AT347677B/de active
- 1976-04-12 SU SU762350306A patent/SU795488A3/ru active
- 1976-04-12 DK DK168976A patent/DK149864C/da not_active IP Right Cessation
- 1976-04-12 SE SE7604279A patent/SE430253B/xx not_active IP Right Cessation
- 1976-04-13 NL NL7603907.A patent/NL164569C/xx not_active IP Right Cessation
- 1976-04-13 GB GB15054/76A patent/GB1490509A/en not_active Expired
- 1976-04-14 FI FI761019A patent/FI61494C/fi not_active IP Right Cessation
-
1979
- 1979-08-22 JP JP54107054A patent/JPS5846204B2/ja not_active Expired
Also Published As
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |