MXPA06001656A - Sistema catalitico para obtencion de copolimeros de dieno conjugado/monoolefina y estos copolimeros. - Google Patents
Sistema catalitico para obtencion de copolimeros de dieno conjugado/monoolefina y estos copolimeros.Info
- Publication number
- MXPA06001656A MXPA06001656A MXPA06001656A MXPA06001656A MXPA06001656A MX PA06001656 A MXPA06001656 A MX PA06001656A MX PA06001656 A MXPA06001656 A MX PA06001656A MX PA06001656 A MXPA06001656 A MX PA06001656A MX PA06001656 A MXPA06001656 A MX PA06001656A
- Authority
- MX
- Mexico
- Prior art keywords
- copolymer
- butadiene
- catalyst
- catalytic system
- equal
- Prior art date
Links
- 229920001577 copolymer Polymers 0.000 title claims abstract description 150
- 150000001993 dienes Chemical class 0.000 title claims abstract description 51
- 230000003197 catalytic effect Effects 0.000 title claims abstract description 43
- 150000005673 monoalkenes Chemical class 0.000 title claims abstract description 16
- 238000004519 manufacturing process Methods 0.000 title claims abstract 4
- 229920000089 Cyclic olefin copolymer Polymers 0.000 title description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims abstract description 69
- 239000003426 co-catalyst Substances 0.000 claims abstract description 48
- 125000002524 organometallic group Chemical group 0.000 claims abstract description 48
- 239000000203 mixture Substances 0.000 claims abstract description 39
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 22
- 239000003446 ligand Substances 0.000 claims abstract description 15
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 13
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 claims abstract description 13
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims abstract description 13
- 150000002602 lanthanoids Chemical group 0.000 claims abstract description 13
- 230000000536 complexating effect Effects 0.000 claims abstract description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 8
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 5
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims abstract description 5
- 125000005234 alkyl aluminium group Chemical group 0.000 claims abstract description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 5
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 5
- 239000000460 chlorine Substances 0.000 claims abstract description 5
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 5
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 5
- 239000011737 fluorine Substances 0.000 claims abstract description 5
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims abstract description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 4
- 150000004795 grignard reagents Chemical class 0.000 claims abstract description 4
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 4
- 150000002367 halogens Chemical class 0.000 claims abstract description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 4
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 225
- 239000004711 α-olefin Substances 0.000 claims description 53
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 claims description 48
- 238000000034 method Methods 0.000 claims description 45
- 229910052779 Neodymium Inorganic materials 0.000 claims description 37
- QEFYFXOXNSNQGX-UHFFFAOYSA-N neodymium atom Chemical compound [Nd] QEFYFXOXNSNQGX-UHFFFAOYSA-N 0.000 claims description 36
- 230000008569 process Effects 0.000 claims description 36
- 239000003054 catalyst Substances 0.000 claims description 32
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 25
- 239000005977 Ethylene Substances 0.000 claims description 25
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 claims description 24
- 238000002360 preparation method Methods 0.000 claims description 24
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 claims description 22
- 238000007334 copolymerization reaction Methods 0.000 claims description 22
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 20
- 239000002904 solvent Substances 0.000 claims description 19
- -1 alkyl lithium Chemical compound 0.000 claims description 18
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 claims description 16
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 16
- 238000006243 chemical reaction Methods 0.000 claims description 12
- 229920001897 terpolymer Polymers 0.000 claims description 10
- 229910052747 lanthanoid Inorganic materials 0.000 claims description 9
- 229910052744 lithium Inorganic materials 0.000 claims description 9
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- OFHCOWSQAMBJIW-AVJTYSNKSA-N alfacalcidol Chemical compound C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)CCCC(C)C)=C\C=C1\C[C@@H](O)C[C@H](O)C1=C OFHCOWSQAMBJIW-AVJTYSNKSA-N 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 6
- 239000000470 constituent Substances 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- 229910052782 aluminium Inorganic materials 0.000 claims description 5
- SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 claims description 5
- KXDANLFHGCWFRQ-UHFFFAOYSA-N magnesium;butane;octane Chemical compound [Mg+2].CCC[CH2-].CCCCCCC[CH2-] KXDANLFHGCWFRQ-UHFFFAOYSA-N 0.000 claims description 5
- 230000000737 periodic effect Effects 0.000 claims description 5
- 239000001273 butane Substances 0.000 claims description 4
- 125000004122 cyclic group Chemical group 0.000 claims description 4
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 claims description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims description 4
- 238000001704 evaporation Methods 0.000 claims description 3
- 230000008020 evaporation Effects 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 239000004215 Carbon black (E152) Substances 0.000 claims description 2
- 238000002425 crystallisation Methods 0.000 claims description 2
- 230000008025 crystallization Effects 0.000 claims description 2
- 238000009826 distribution Methods 0.000 claims description 2
- 238000000605 extraction Methods 0.000 claims description 2
- 229930195733 hydrocarbon Natural products 0.000 claims description 2
- 150000002430 hydrocarbons Chemical class 0.000 claims description 2
- 229910003002 lithium salt Inorganic materials 0.000 claims description 2
- 159000000002 lithium salts Chemical class 0.000 claims description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
- 230000005945 translocation Effects 0.000 claims description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 2
- 229920002554 vinyl polymer Polymers 0.000 claims description 2
- 239000003153 chemical reaction reagent Substances 0.000 claims 1
- ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 abstract description 4
- 235000001055 magnesium Nutrition 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 45
- 238000006116 polymerization reaction Methods 0.000 description 32
- 238000005481 NMR spectroscopy Methods 0.000 description 26
- 238000004458 analytical method Methods 0.000 description 22
- 238000003780 insertion Methods 0.000 description 19
- 230000037431 insertion Effects 0.000 description 19
- 238000001816 cooling Methods 0.000 description 16
- 238000001228 spectrum Methods 0.000 description 16
- 239000012300 argon atmosphere Substances 0.000 description 15
- 238000007872 degassing Methods 0.000 description 15
- 238000001035 drying Methods 0.000 description 15
- 238000001556 precipitation Methods 0.000 description 15
- 230000035484 reaction time Effects 0.000 description 15
- QNRMTGGDHLBXQZ-UHFFFAOYSA-N buta-1,2-diene Chemical compound CC=C=C QNRMTGGDHLBXQZ-UHFFFAOYSA-N 0.000 description 13
- GQEZCXVZFLOKMC-UHFFFAOYSA-N 1-hexadecene Chemical compound CCCCCCCCCCCCCCC=C GQEZCXVZFLOKMC-UHFFFAOYSA-N 0.000 description 10
- 230000009477 glass transition Effects 0.000 description 10
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 8
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 8
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 8
- 238000012360 testing method Methods 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 150000001336 alkenes Chemical class 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 4
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical group C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 4
- YXWMQONSXLHPBZ-UHFFFAOYSA-N buta-1,3-diene;hex-1-ene Chemical compound C=CC=C.CCCCC=C YXWMQONSXLHPBZ-UHFFFAOYSA-N 0.000 description 4
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 4
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- WWSJZGAPAVMETJ-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-3-ethoxypyrazol-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C=1C(=NN(C=1)CC(=O)N1CC2=C(CC1)NN=N2)OCC WWSJZGAPAVMETJ-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 239000005062 Polybutadiene Substances 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000013256 coordination polymer Substances 0.000 description 3
- 229920002857 polybutadiene Polymers 0.000 description 3
- 229910052720 vanadium Inorganic materials 0.000 description 3
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 description 3
- 239000003643 water by type Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 2
- 229920005603 alternating copolymer Polymers 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- HQQADJVZYDDRJT-UHFFFAOYSA-N ethene;prop-1-ene Chemical group C=C.CC=C HQQADJVZYDDRJT-UHFFFAOYSA-N 0.000 description 2
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 229910052719 titanium Inorganic materials 0.000 description 2
- 239000010936 titanium Substances 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
- 229910052723 transition metal Inorganic materials 0.000 description 2
- 150000003624 transition metals Chemical class 0.000 description 2
- 150000003681 vanadium Chemical class 0.000 description 2
- CRSBERNSMYQZNG-UHFFFAOYSA-N 1 -dodecene Natural products CCCCCCCCCCC=C CRSBERNSMYQZNG-UHFFFAOYSA-N 0.000 description 1
- HMUNWXXNJPVALC-UHFFFAOYSA-N 1-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)C(CN1CC2=C(CC1)NN=N2)=O HMUNWXXNJPVALC-UHFFFAOYSA-N 0.000 description 1
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 1
- LDXJRKWFNNFDSA-UHFFFAOYSA-N 2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]ethanone Chemical compound C1CN(CC2=NNN=C21)CC(=O)N3CCN(CC3)C4=CN=C(N=C4)NCC5=CC(=CC=C5)OC(F)(F)F LDXJRKWFNNFDSA-UHFFFAOYSA-N 0.000 description 1
- VWVRASTUFJRTHW-UHFFFAOYSA-N 2-[3-(azetidin-3-yloxy)-4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]pyrazol-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound O=C(CN1C=C(C(OC2CNC2)=N1)C1=CN=C(NC2CC3=C(C2)C=CC=C3)N=C1)N1CCC2=C(C1)N=NN2 VWVRASTUFJRTHW-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- NCGICGYLBXGBGN-UHFFFAOYSA-N 3-morpholin-4-yl-1-oxa-3-azonia-2-azanidacyclopent-3-en-5-imine;hydrochloride Chemical compound Cl.[N-]1OC(=N)C=[N+]1N1CCOCC1 NCGICGYLBXGBGN-UHFFFAOYSA-N 0.000 description 1
- 101100219382 Caenorhabditis elegans cah-2 gene Proteins 0.000 description 1
- LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical compound C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 description 1
- 102100037186 Cytochrome b-245 chaperone 1 Human genes 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- 241001505295 Eros Species 0.000 description 1
- 239000007818 Grignard reagent Substances 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000002879 Lewis base Substances 0.000 description 1
- 229910017544 NdCl3 Inorganic materials 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 229910052772 Samarium Inorganic materials 0.000 description 1
- 229910003074 TiCl4 Inorganic materials 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- VWARDJVPFDTYFV-UHFFFAOYSA-N buta-1,3-diene but-1-ene Chemical compound CCC=C.C=CC=C VWARDJVPFDTYFV-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 238000004737 colorimetric analysis Methods 0.000 description 1
- 101150064521 cybC1 gene Proteins 0.000 description 1
- 230000009849 deactivation Effects 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 229940069096 dodecene Drugs 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- ALSOCDGAZNNNME-UHFFFAOYSA-N ethene;hex-1-ene Chemical group C=C.CCCCC=C ALSOCDGAZNNNME-UHFFFAOYSA-N 0.000 description 1
- 229920001038 ethylene copolymer Polymers 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 229910052732 germanium Inorganic materials 0.000 description 1
- 229910052735 hafnium Inorganic materials 0.000 description 1
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 239000002815 homogeneous catalyst Substances 0.000 description 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 229910052746 lanthanum Inorganic materials 0.000 description 1
- FZLIPJUXYLNCLC-UHFFFAOYSA-N lanthanum atom Chemical compound [La] FZLIPJUXYLNCLC-UHFFFAOYSA-N 0.000 description 1
- 150000007527 lewis bases Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 238000009862 microstructural analysis Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- ARWCRSVRKCNEDI-UHFFFAOYSA-K neodymium(3+);octanoate Chemical compound [Nd+3].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O.CCCCCCCC([O-])=O ARWCRSVRKCNEDI-UHFFFAOYSA-K 0.000 description 1
- ATINCSYRHURBSP-UHFFFAOYSA-K neodymium(iii) chloride Chemical compound Cl[Nd](Cl)Cl ATINCSYRHURBSP-UHFFFAOYSA-K 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- WYURNTSHIVDZCO-SVYQBANQSA-N oxolane-d8 Chemical compound [2H]C1([2H])OC([2H])([2H])C([2H])([2H])C1([2H])[2H] WYURNTSHIVDZCO-SVYQBANQSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 238000011002 quantification Methods 0.000 description 1
- 229910052704 radon Inorganic materials 0.000 description 1
- 229920005604 random copolymer Polymers 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 238000001542 size-exclusion chromatography Methods 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 229950011008 tetrachloroethylene Drugs 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 150000003608 titanium Chemical class 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- 229910052726 zirconium Inorganic materials 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
- 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
- C08F4/58—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 silicon, germanium, tin, lead, antimony, bismuth or compounds thereof
-
- 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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- 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
- C08F236/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds
- C08F236/02—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds
- C08F236/04—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds conjugated
-
- C—CHEMISTRY; METALLURGY
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F4/00—Polymerisation catalysts
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F210/00—Copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
- C08F210/02—Ethene
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F210/00—Copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
- C08F210/04—Monomers containing three or four carbon atoms
- C08F210/06—Propene
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F210/00—Copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
- C08F210/14—Monomers containing five or more carbon atoms
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F210/00—Copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
- C08F210/16—Copolymers of ethene with alpha-alkenes, e.g. EP rubbers
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S526/00—Synthetic resins or natural rubbers -- part of the class 520 series
- Y10S526/943—Polymerization with metallocene catalysts
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- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Polymerization Catalysts (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
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Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0309930A FR2858817B1 (fr) | 2003-08-13 | 2003-08-13 | Systeme catalytique pour l'obtention de copolymeres diene(s) conjugue(s)/ mono-olefine(s) et ces copolymeres |
| PCT/EP2004/008336 WO2005028526A1 (fr) | 2003-08-13 | 2004-07-26 | Système catalytique pour l'obtention de copolymères diène(s) conjugué(s) / mono-oléfine(s) et ces copolymères |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| MXPA06001656A true MXPA06001656A (es) | 2006-08-11 |
Family
ID=34112767
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MXPA06001656A MXPA06001656A (es) | 2003-08-13 | 2004-07-26 | Sistema catalitico para obtencion de copolimeros de dieno conjugado/monoolefina y estos copolimeros. |
Country Status (10)
| Country | Link |
|---|---|
| US (2) | US7547654B2 (https=) |
| EP (1) | EP1656400B1 (https=) |
| JP (1) | JP5329040B2 (https=) |
| KR (2) | KR101263815B1 (https=) |
| CN (1) | CN100567343C (https=) |
| BR (1) | BRPI0413457B1 (https=) |
| FR (1) | FR2858817B1 (https=) |
| MX (1) | MXPA06001656A (https=) |
| RU (1) | RU2400492C2 (https=) |
| WO (1) | WO2005028526A1 (https=) |
Families Citing this family (59)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2886937B1 (fr) * | 2005-06-14 | 2007-08-10 | Michelin Soc Tech | Procede de preparation d'un elastomere dienique, tel qu'un polybutadiene |
| EP1777240A1 (en) * | 2005-10-24 | 2007-04-25 | Total Petrochemicals Research Feluy | Preparation of styrene-isoprene and of styrene isoprene ethylene copolymers |
| FR2893029B1 (fr) * | 2005-11-09 | 2009-01-16 | Michelin Soc Tech | Complexe metallocene borohydrure d'un lanthanide, systeme catalytique l'incorporant, procede de polymerisation l'utilisant et copolymere ethylene/butadiene obtenu par ce procede |
| US8048961B2 (en) * | 2006-08-25 | 2011-11-01 | Dow Global Technologies Llc | Production of metathesis products by amorphous polymer segment interchange |
| US8530579B2 (en) * | 2006-08-25 | 2013-09-10 | Dow Global Technologies Llc | Production of metathesis products by high melting polymer segment interchange |
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| JP5917809B2 (ja) * | 2010-11-30 | 2016-05-18 | 株式会社ブリヂストン | 共重合体及びその製造方法、並びに、ゴム組成物、架橋ゴム組成物、及びタイヤ |
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| JP5898975B2 (ja) * | 2012-01-27 | 2016-04-06 | 株式会社ブリヂストン | 共重合体における単量体単位の含有割合の制御方法 |
| WO2014052957A1 (en) | 2012-09-30 | 2014-04-03 | Bridgestone Corporation | Organometallic catalyst complex and polymerization method employing same |
| WO2014055868A1 (en) | 2012-10-04 | 2014-04-10 | Bridgestone Corporation | Organometallic complex catalyst and polymerization method employing same |
| FR3001223B1 (fr) | 2013-01-22 | 2015-03-06 | Michelin & Cie | Composition de caoutchouc comprenant un elastomere dienique fortement sature |
| EP3148937B1 (en) | 2014-05-30 | 2019-09-18 | Bridgestone Corporation | Metallic complex catalyst and polymerization methods employing same |
| EP3738927A1 (en) | 2014-05-31 | 2020-11-18 | Bridgestone Corporation | Metallic complex catalyst, polymerization methods employing same and polymer products thereof |
| WO2016139996A1 (ja) | 2015-03-04 | 2016-09-09 | Jsr株式会社 | 共重合体、重合体組成物及び架橋重合体 |
| FR3037588B1 (fr) | 2015-06-19 | 2017-05-19 | Michelin & Cie | Copolymere elastomere thermoplastique a base d'elastomere dienique et de polypropylene, compositions le comprenant et procede de preparation |
| CN108137731B (zh) | 2015-08-31 | 2020-08-25 | 株式会社普利司通 | 多烯和烯烃的共聚 |
| WO2017065300A1 (ja) * | 2015-10-16 | 2017-04-20 | 株式会社ブリヂストン | 多元共重合体、樹脂組成物、架橋樹脂組成物、及び製品 |
| EP3363824B1 (en) * | 2015-10-16 | 2024-05-01 | Bridgestone Corporation | Multicomponent copolymer, rubber composition, cross-linked rubber composition, rubber product, and tire |
| FR3044010A1 (fr) | 2015-11-19 | 2017-05-26 | Michelin & Cie | Bande de roulement pour pneumatique d'avion |
| FR3044007B1 (fr) | 2015-11-19 | 2017-12-08 | Michelin & Cie | Bande de roulement pour pneumatique d'avion |
| FR3044663B1 (fr) * | 2015-12-08 | 2017-12-29 | Michelin & Cie | Copolymere monofonctionnel ou telechelique de 1,3-butadiene et d'ethylene. |
| FR3044664B1 (fr) | 2015-12-08 | 2017-12-29 | Michelin & Cie | Copolymere monofonctionnel ou telechelique de 1,3-diene et d'ethylene ou d'alpha-monoolefine. |
| FR3045613B1 (fr) | 2015-12-17 | 2017-12-15 | Michelin & Cie | Copolymere d'ethylene et de butadiene de microstructure homogene |
| FR3045633B1 (fr) | 2015-12-22 | 2017-12-15 | Michelin & Cie | Pneumatique comprenant une composition de caoutchouc comprenant un elastomere dienique substitue |
| FR3060007A1 (fr) * | 2016-12-09 | 2018-06-15 | Compagnie Generale Des Etablissements Michelin | Terpolymeres d'ethylene, de 1,3-butadiene ou d'isoprene, et d'une alpha-monoolefine aromatique |
| FR3060592A1 (fr) | 2016-12-15 | 2018-06-22 | Compagnie Generale Des Etablissements Michelin | Pneumatique comportant une composition de caoutchouc comprenant un polymere porteur d'un groupement diene conjugue reticule par un dienophile |
| FR3060576A1 (fr) | 2016-12-15 | 2018-06-22 | Compagnie Generale Des Etablissements Michelin | Elastomere dienique portant des groupes pendants anthracenyles |
| FR3060570A1 (fr) | 2016-12-19 | 2018-06-22 | Compagnie Generale Des Etablissements Michelin | Procede de preparation d'un elastomere dienique modifie par un compose 1,3-dipolaire par extrusion reactive |
| FR3060571A1 (fr) | 2016-12-19 | 2018-06-22 | Compagnie Generale Des Etablissements Michelin | Procede de preparation d'un elastomere dienique modifie par un compose 1,3-dipolaire |
| FR3063731A1 (fr) | 2017-03-08 | 2018-09-14 | Compagnie Generale Des Etablissements Michelin | Pneumatique muni d'une composition comprenant un elastomere riche en ethylene, un peroxyde et un acrylate de zinc |
| FR3063732A1 (fr) | 2017-03-08 | 2018-09-14 | Compagnie Generale Des Etablissements Michelin | Pneumatique muni d'une composition comprenant un elastomere riche en ethylene, un peroxyde et un derive d'acrylate polyfonctionnel |
| WO2019002756A1 (fr) | 2017-06-28 | 2019-01-03 | Compagnie Generale Des Etablissements Michelin | Elastomère diénique portant des groupes imidazole |
| FR3068698A1 (fr) | 2017-07-04 | 2019-01-11 | Compagnie Generale Des Etablissements Michelin | Polymere portant des groupes pendants fonctionnels particuliers imidazolidinone |
| FR3068703A1 (fr) | 2017-07-04 | 2019-01-11 | Compagnie Generale Des Etablissements Michelin | Composition a base d'au moins un compose polyaromatique particulier |
| FR3069550A1 (fr) | 2017-07-28 | 2019-02-01 | Compagnie Generale Des Etablissements Michelin | Elastomere etendu a la resine |
| WO2019102132A1 (fr) | 2017-11-21 | 2019-05-31 | Compagnie Generale Des Etablissements Michelin | Composition de caoutchouc |
| EP3713924B1 (fr) | 2017-11-21 | 2023-01-04 | Compagnie Générale des Etablissements Michelin | Composé 1,3-dipolaire comportant un groupe époxyde |
| WO2019102126A1 (fr) | 2017-11-21 | 2019-05-31 | Compagnie Generale Des Etablissements Michelin | Polymère diénique modifié par un groupe époxyde |
| EP3713774B1 (fr) | 2017-11-21 | 2022-03-09 | Compagnie Générale des Etablissements Michelin | Composition de caoutchouc |
| JP7002310B2 (ja) * | 2017-12-05 | 2022-02-04 | 株式会社ブリヂストン | 多元共重合体の製造方法 |
| JP2019099719A (ja) | 2017-12-05 | 2019-06-24 | 株式会社ブリヂストン | 共重合体、ゴム組成物、樹脂組成物、タイヤ及び樹脂製品 |
| JP6983048B2 (ja) * | 2017-12-05 | 2021-12-17 | 株式会社ブリヂストン | 共重合体、ゴム組成物、樹脂組成物、タイヤ及び樹脂製品 |
| EP3720700A1 (fr) | 2017-12-06 | 2020-10-14 | Compagnie Générale des Etablissements Michelin | Stratifié élastomère |
| WO2019110926A1 (fr) | 2017-12-06 | 2019-06-13 | Compagnie Generale Des Etablissements Michelin | Stratifie elastomere |
| FR3085166B1 (fr) | 2018-08-23 | 2020-07-17 | Compagnie Generale Des Etablissements Michelin | Pneumatique muni d'une composition comprenant un elastomere riche en ethylene, un peroxyde et un derive d'acrylate specifique |
| FR3085165B1 (fr) | 2018-08-23 | 2020-07-17 | Compagnie Generale Des Etablissements Michelin | Pneumatique muni d'une composition comprenant un elastomere riche en ethylene, un peroxyde et un derive d'acrylate specifique |
| FR3085167B1 (fr) | 2018-08-23 | 2020-07-31 | Michelin & Cie | Pneumatique muni d'une composition comprenant un elastomere riche en ethylene, un peroxyde et un derive d'acrylate specifique |
| FR3088328B3 (fr) | 2018-11-09 | 2020-12-04 | Michelin & Cie | Elastomere dienique fonctionnel et composition de caoutchouc |
| FR3104584B1 (fr) | 2019-12-17 | 2021-12-03 | Michelin & Cie | Composé diorganomagnésien asymétrique |
| FR3104586B1 (fr) * | 2019-12-17 | 2021-12-03 | Michelin & Cie | Composé diorganomagnésien asymétrique pour système catalytique |
| FR3116276B1 (fr) | 2020-11-19 | 2023-11-10 | Michelin & Cie | Diorganomagnésien ayant une chaîne diénique ou oléfinique et fonctionnelle amine |
| FR3116277A1 (fr) | 2020-11-19 | 2022-05-20 | Compagnie Generale Des Etablissements Michelin | Copolymères fonctionnels amine à blocs éthyléniques et diéniques |
| FR3116538B1 (fr) | 2020-11-24 | 2022-11-25 | Michelin & Cie | Co-catalyseur comprenant plusieurs liaisons carbone magnésium |
| CN120981495A (zh) | 2023-02-08 | 2025-11-18 | 埃克森美孚技术与工程公司 | 用于共聚的催化剂 |
| KR20260015988A (ko) | 2023-06-06 | 2026-02-03 | 엑손모빌 테크놀로지 앤드 엔지니어링 컴퍼니 | 용액 촉매계 및 이의 용도 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3898207A (en) * | 1974-03-25 | 1975-08-05 | Firestone Tire & Rubber Co | Process for polymerizing conjugated dienes |
| US5278272A (en) * | 1991-10-15 | 1994-01-11 | The Dow Chemical Company | Elastic substantialy linear olefin polymers |
| IT1256259B (it) * | 1992-12-30 | 1995-11-29 | Montecatini Tecnologie Srl | Composti mettallocenici aventi leganti di tipo fluorenilico |
| IT1273753B (it) * | 1994-02-11 | 1997-07-10 | Eniriceche Spa | Sistema catalitico e processo per la produzione di polidiolefine |
| JPH07258319A (ja) * | 1994-03-23 | 1995-10-09 | Mitsubishi Rayon Co Ltd | 有機金属触媒及びそれを用いたビニル系重合体の製造方法 |
| JPH1180269A (ja) * | 1997-07-18 | 1999-03-26 | Mitsui Chem Inc | 不飽和性共重合体、その製造方法および該共重合体系組成物 |
| EP0891993B1 (en) * | 1997-07-18 | 2003-05-02 | Mitsui Chemicals, Inc. | Unsaturated copolymers, processes for preparing the same, and compositions containing the same |
| CN1240796A (zh) * | 1998-06-11 | 2000-01-12 | 意大利燃料添加剂股份公司 | 含α－烯烃的乙烯聚合物 |
| FR2799468B1 (fr) * | 1999-10-12 | 2006-04-28 | Michelin Soc Tech | Systeme catalytique utilisable pour la copolymerisation de l'ethylene et d'un diene conjugue, procede de preparation de ce systeme catalytique et d'un copolymere d'ethylene et d'un diene conjugue |
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2003
- 2003-08-13 FR FR0309930A patent/FR2858817B1/fr not_active Expired - Fee Related
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- 2004-07-26 KR KR1020127017251A patent/KR101263815B1/ko not_active Expired - Fee Related
- 2004-07-26 RU RU2006107530/04A patent/RU2400492C2/ru not_active IP Right Cessation
- 2004-07-26 WO PCT/EP2004/008336 patent/WO2005028526A1/fr not_active Ceased
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- 2004-07-26 KR KR1020067002964A patent/KR101196236B1/ko not_active Expired - Fee Related
- 2004-07-26 EP EP04763491.0A patent/EP1656400B1/fr not_active Expired - Lifetime
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Also Published As
| Publication number | Publication date |
|---|---|
| RU2006107530A (ru) | 2006-06-27 |
| KR20120082478A (ko) | 2012-07-23 |
| KR20060088100A (ko) | 2006-08-03 |
| CN1835978A (zh) | 2006-09-20 |
| JP2007501881A (ja) | 2007-02-01 |
| JP5329040B2 (ja) | 2013-10-30 |
| FR2858817B1 (fr) | 2006-02-03 |
| US20060160969A1 (en) | 2006-07-20 |
| BRPI0413457B1 (pt) | 2014-09-09 |
| FR2858817A1 (fr) | 2005-02-18 |
| BRPI0413457A (pt) | 2006-10-17 |
| EP1656400A1 (fr) | 2006-05-17 |
| KR101196236B1 (ko) | 2012-11-05 |
| CN100567343C (zh) | 2009-12-09 |
| EP1656400B1 (fr) | 2019-05-29 |
| US8039565B2 (en) | 2011-10-18 |
| KR101263815B1 (ko) | 2013-05-13 |
| US7547654B2 (en) | 2009-06-16 |
| US20090270578A1 (en) | 2009-10-29 |
| WO2005028526A1 (fr) | 2005-03-31 |
| RU2400492C2 (ru) | 2010-09-27 |
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