CA2321362C - Systeme catalytique, son procede de preparation et procede de preparation d'un copolymere d'ethylene et d'un diene conjugue - Google Patents
Systeme catalytique, son procede de preparation et procede de preparation d'un copolymere d'ethylene et d'un diene conjugue Download PDFInfo
- Publication number
- CA2321362C CA2321362C CA2321362A CA2321362A CA2321362C CA 2321362 C CA2321362 C CA 2321362C CA 2321362 A CA2321362 A CA 2321362A CA 2321362 A CA2321362 A CA 2321362A CA 2321362 C CA2321362 C CA 2321362C
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- Prior art keywords
- formula
- alkyl
- copolymer
- ethylene
- complex
- 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 - Fee Related
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- 230000003197 catalytic effect Effects 0.000 title claims abstract description 29
- 150000001993 dienes Chemical class 0.000 title claims description 34
- 238000000034 method Methods 0.000 title claims description 31
- 229920001038 ethylene copolymer Polymers 0.000 title description 4
- 125000002524 organometallic group Chemical group 0.000 claims abstract description 61
- -1 alkyl magnesium Chemical compound 0.000 claims abstract description 26
- 239000003426 co-catalyst Substances 0.000 claims abstract description 25
- 150000003839 salts Chemical class 0.000 claims abstract description 21
- 230000000536 complexating effect Effects 0.000 claims abstract description 20
- 229910052747 lanthanoid Inorganic materials 0.000 claims abstract description 20
- 150000002602 lanthanoids Chemical class 0.000 claims abstract description 20
- 239000002904 solvent Substances 0.000 claims abstract description 20
- 229910052779 Neodymium Inorganic materials 0.000 claims abstract description 19
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 claims abstract description 19
- QEFYFXOXNSNQGX-UHFFFAOYSA-N neodymium atom Chemical compound [Nd] QEFYFXOXNSNQGX-UHFFFAOYSA-N 0.000 claims abstract description 19
- 229910052744 lithium Inorganic materials 0.000 claims abstract description 14
- 229910052751 metal Inorganic materials 0.000 claims abstract description 14
- 239000002184 metal Substances 0.000 claims abstract description 14
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims abstract description 12
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 12
- ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 claims abstract description 11
- 239000003446 ligand Substances 0.000 claims abstract description 11
- 238000002360 preparation method Methods 0.000 claims abstract description 11
- 125000005234 alkyl aluminium group Chemical group 0.000 claims abstract description 10
- 239000011777 magnesium Substances 0.000 claims abstract description 8
- 229910052749 magnesium Inorganic materials 0.000 claims abstract description 8
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 6
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 6
- 238000001704 evaporation Methods 0.000 claims abstract description 6
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 6
- 150000004795 grignard reagents Chemical class 0.000 claims abstract description 6
- 125000005103 alkyl silyl group Chemical group 0.000 claims abstract description 5
- 229910003002 lithium salt Inorganic materials 0.000 claims abstract description 5
- 159000000002 lithium salts Chemical class 0.000 claims abstract description 5
- 230000000737 periodic effect Effects 0.000 claims abstract description 4
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 88
- 229920001577 copolymer Polymers 0.000 claims description 81
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 50
- 239000005977 Ethylene Substances 0.000 claims description 50
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 claims description 47
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 46
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 claims description 32
- 239000000203 mixture Substances 0.000 claims description 32
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 30
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 24
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 23
- 238000004519 manufacturing process Methods 0.000 claims description 21
- 229910052799 carbon Inorganic materials 0.000 claims description 12
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 239000003054 catalyst Substances 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
- 239000000460 chlorine Substances 0.000 claims description 5
- 239000011737 fluorine Substances 0.000 claims description 5
- 150000002367 halogens Chemical group 0.000 claims description 5
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-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
- 239000000725 suspension Substances 0.000 claims description 5
- 239000007818 Grignard reagent Substances 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 239000000470 constituent Substances 0.000 claims description 4
- HEUNOCMGZULNRR-UHFFFAOYSA-N 1-chlorobutane;magnesium Chemical compound [Mg].CCCCCl HEUNOCMGZULNRR-UHFFFAOYSA-N 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims description 3
- 238000000605 extraction Methods 0.000 claims description 3
- 239000012429 reaction media Substances 0.000 claims description 3
- 229910052710 silicon Inorganic materials 0.000 claims description 3
- 239000010703 silicon Substances 0.000 claims description 3
- 239000004215 Carbon black (E152) Substances 0.000 claims description 2
- 239000003153 chemical reaction reagent Substances 0.000 claims description 2
- 229930195733 hydrocarbon Natural products 0.000 claims description 2
- 150000002430 hydrocarbons Chemical class 0.000 claims description 2
- SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 claims 1
- SMBQBQBNOXIFSF-UHFFFAOYSA-N dilithium Chemical compound [Li][Li] SMBQBQBNOXIFSF-UHFFFAOYSA-N 0.000 claims 1
- UWNADWZGEHDQAB-UHFFFAOYSA-N i-Pr2C2H4i-Pr2 Natural products CC(C)CCC(C)C UWNADWZGEHDQAB-UHFFFAOYSA-N 0.000 claims 1
- 229910052740 iodine Inorganic materials 0.000 abstract description 5
- 229910007161 Si(CH3)3 Inorganic materials 0.000 abstract 1
- 150000008064 anhydrides Chemical class 0.000 abstract 1
- 125000001475 halogen functional group Chemical group 0.000 abstract 1
- 238000003780 insertion Methods 0.000 description 21
- 230000037431 insertion Effects 0.000 description 21
- 239000000243 solution Substances 0.000 description 14
- 238000001228 spectrum Methods 0.000 description 14
- 238000005481 NMR spectroscopy Methods 0.000 description 11
- 150000001875 compounds Chemical class 0.000 description 11
- 238000010992 reflux Methods 0.000 description 10
- 230000015572 biosynthetic process Effects 0.000 description 9
- 238000010586 diagram Methods 0.000 description 9
- 238000003786 synthesis reaction Methods 0.000 description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000007334 copolymerization reaction Methods 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 101100441175 Schizosaccharomyces pombe (strain 972 / ATCC 24843) csh3 gene Proteins 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 230000007935 neutral effect Effects 0.000 description 5
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 4
- 238000004364 calculation method Methods 0.000 description 4
- 125000001309 chloro group Chemical group Cl* 0.000 description 4
- 239000013256 coordination polymer Substances 0.000 description 4
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 229910052782 aluminium Inorganic materials 0.000 description 3
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- ATINCSYRHURBSP-UHFFFAOYSA-K neodymium(iii) chloride Chemical compound Cl[Nd](Cl)Cl ATINCSYRHURBSP-UHFFFAOYSA-K 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- 101100352919 Caenorhabditis elegans ppm-2 gene Proteins 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 229910017544 NdCl3 Inorganic materials 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 235000019270 ammonium chloride Nutrition 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000007872 degassing Methods 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- CPOFMOWDMVWCLF-UHFFFAOYSA-N methyl(oxo)alumane Chemical compound C[Al]=O CPOFMOWDMVWCLF-UHFFFAOYSA-N 0.000 description 2
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 125000002348 vinylic group Chemical group 0.000 description 2
- APPOKADJQUIAHP-GGWOSOGESA-N (2e,4e)-hexa-2,4-diene Chemical compound C\C=C\C=C\C APPOKADJQUIAHP-GGWOSOGESA-N 0.000 description 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical compound C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- SDJHPPZKZZWAKF-UHFFFAOYSA-N 2,3-dimethylbuta-1,3-diene Chemical compound CC(=C)C(C)=C SDJHPPZKZZWAKF-UHFFFAOYSA-N 0.000 description 1
- HMWCQCYUKQZPRA-UHFFFAOYSA-N 2,4-dimethyl-3-methylidenepent-1-ene Chemical compound CC(C)C(=C)C(C)=C HMWCQCYUKQZPRA-UHFFFAOYSA-N 0.000 description 1
- PJXJBPMWCKMWLS-UHFFFAOYSA-N 2-methyl-3-methylidenepent-1-ene Chemical compound CCC(=C)C(C)=C PJXJBPMWCKMWLS-UHFFFAOYSA-N 0.000 description 1
- OAOZZYBUAWEDRA-UHFFFAOYSA-N 3,4-dimethylidenehexane Chemical compound CCC(=C)C(=C)CC OAOZZYBUAWEDRA-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 229910018540 Si C Inorganic materials 0.000 description 1
- VSKBCRUQHHGABO-UHFFFAOYSA-N [Al].[H][H].[H][H].[H][H] Chemical compound [Al].[H][H].[H][H].[H][H] VSKBCRUQHHGABO-UHFFFAOYSA-N 0.000 description 1
- 229920005603 alternating copolymer Polymers 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 101150117004 atg18 gene Proteins 0.000 description 1
- 238000012550 audit Methods 0.000 description 1
- QNRMTGGDHLBXQZ-UHFFFAOYSA-N buta-1,2-diene Chemical compound CC=C=C QNRMTGGDHLBXQZ-UHFFFAOYSA-N 0.000 description 1
- XZKRXPZXQLARHH-UHFFFAOYSA-N buta-1,3-dienylbenzene Chemical compound C=CC=CC1=CC=CC=C1 XZKRXPZXQLARHH-UHFFFAOYSA-N 0.000 description 1
- 238000010668 complexation reaction Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- QUXHCILOWRXCEO-UHFFFAOYSA-M magnesium;butane;chloride Chemical compound [Mg+2].[Cl-].CCC[CH2-] QUXHCILOWRXCEO-UHFFFAOYSA-M 0.000 description 1
- XONPDZSGENTBNJ-UHFFFAOYSA-N molecular hydrogen;sodium Chemical compound [Na].[H][H] XONPDZSGENTBNJ-UHFFFAOYSA-N 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Natural products CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 description 1
- 239000002685 polymerization catalyst Substances 0.000 description 1
- 229910052761 rare earth metal Inorganic materials 0.000 description 1
- 150000002910 rare earth metals Chemical class 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 229920006301 statistical copolymer Polymers 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000001291 vacuum drying Methods 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
- C08F4/60—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
- C08F4/68—Vanadium, niobium, tantalum 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
- 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
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L23/00—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
- C08L23/02—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers not modified by chemical after-treatment
- C08L23/04—Homopolymers or copolymers of ethene
- C08L23/08—Copolymers of ethene
- C08L23/0807—Copolymers of ethene with unsaturated hydrocarbons only containing four or more carbon atoms
- C08L23/0815—Copolymers of ethene with unsaturated hydrocarbons only containing four or more carbon atoms with aliphatic 1-olefins containing one carbon-to-carbon double bond
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2205/00—Polymer mixtures characterised by other features
- C08L2205/02—Polymer mixtures characterised by other features containing two or more polymers of the same C08L -group
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L23/00—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
- C08L23/02—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers not modified by chemical after-treatment
- C08L23/04—Homopolymers or copolymers of ethene
- C08L23/08—Copolymers of ethene
- C08L23/0807—Copolymers of ethene with unsaturated hydrocarbons only containing four or more carbon atoms
- C08L23/083—Copolymers of ethene with unsaturated hydrocarbons only containing four or more carbon atoms with aliphatic polyenes, i.e. containing two or more carbon-to-carbon double bonds
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S526/00—Synthetic resins or natural rubbers -- part of the class 520 series
- Y10S526/943—Polymerization with metallocene catalysts
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Polymerization Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9912798A FR2799468B1 (fr) | 1999-10-12 | 1999-10-12 | 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 |
| FR99/12798 | 1999-10-12 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2321362A1 CA2321362A1 (fr) | 2001-04-12 |
| CA2321362C true CA2321362C (fr) | 2010-06-15 |
Family
ID=9550906
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2321362A Expired - Fee Related CA2321362C (fr) | 1999-10-12 | 2000-10-10 | Systeme catalytique, son procede de preparation et procede de preparation d'un copolymere d'ethylene et d'un diene conjugue |
Country Status (9)
| Country | Link |
|---|---|
| US (2) | US6569799B1 (enExample) |
| EP (2) | EP1829901B1 (enExample) |
| JP (1) | JP4806784B2 (enExample) |
| KR (1) | KR100722171B1 (enExample) |
| CN (1) | CN1205238C (enExample) |
| AT (1) | ATE537196T1 (enExample) |
| BR (1) | BR0004778B1 (enExample) |
| CA (1) | CA2321362C (enExample) |
| FR (1) | FR2799468B1 (enExample) |
Families Citing this family (140)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100826080B1 (ko) * | 2001-12-27 | 2008-04-29 | 삼성토탈 주식회사 | 고용융체 강도를 갖는 에틸렌/디엔 공중합체의 제조방법 |
| AU2003286138A1 (en) | 2002-10-16 | 2004-05-04 | Atofina Research | Ethylene/butadiene copolymers, catalytic system of producing same and production of said polymers |
| WO2004044018A2 (en) * | 2002-11-07 | 2004-05-27 | Dow Global Technologies, Inc. | Process for homo- or copolymerization of conjugated dienes and in situ formation of polymer blends and products made thereby |
| FR2858817B1 (fr) * | 2003-08-13 | 2006-02-03 | Michelin Soc Tech | Systeme catalytique pour l'obtention de copolymeres diene(s) conjugue(s)/ mono-olefine(s) et ces copolymeres |
| US7294649B2 (en) * | 2004-12-17 | 2007-11-13 | Roche Diagnostics Operatins, Inc. | Methamphetamine derivatives and conjugates for immunoassay |
| WO2007016700A2 (en) * | 2005-08-04 | 2007-02-08 | The Regents Of The University Of Colorado, A Body Corporate | Catalysts for radical polymerization |
| 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 |
| FR2893028B1 (fr) * | 2005-11-09 | 2008-02-15 | 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 |
| FR2893030B1 (fr) * | 2006-10-17 | 2011-04-15 | Michelin Soc Tech | Copolymere ethylene/butadiene |
| US7741418B2 (en) * | 2007-12-31 | 2010-06-22 | Bridgestone Corporation | Process for producing polydienes |
| KR20120052385A (ko) | 2009-08-07 | 2012-05-23 | 가부시키가이샤 브리지스톤 | 공중합체의 제조 방법 |
| FR2954332B1 (fr) | 2009-12-22 | 2012-01-13 | Michelin Soc Tech | Article notamment pneumatique avec melange de caoutchouc externe comportant un sel de lanthanide |
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| JPH07304829A (ja) * | 1994-05-09 | 1995-11-21 | Mitsubishi Chem Corp | 重合体の製造法 |
| JPH08245711A (ja) * | 1995-03-10 | 1996-09-24 | Showa Denko Kk | 新規ランタニド錯体及びこれを用いた不飽和カルボン酸エステル重合体並びにポリオレフィンの製造方法 |
| KR100472591B1 (ko) * | 1996-07-05 | 2005-05-16 | 바이엘 악티엔게젤샤프트 | 고융점폴리올레핀의제조방법 |
-
1999
- 1999-10-12 FR FR9912798A patent/FR2799468B1/fr not_active Expired - Lifetime
-
2000
- 2000-10-06 AT AT00121834T patent/ATE537196T1/de active
- 2000-10-06 EP EP07010599.4A patent/EP1829901B1/fr not_active Expired - Lifetime
- 2000-10-06 EP EP00121834A patent/EP1092731B1/fr not_active Expired - Lifetime
- 2000-10-10 CA CA2321362A patent/CA2321362C/fr not_active Expired - Fee Related
- 2000-10-11 BR BRPI0004778-3A patent/BR0004778B1/pt not_active IP Right Cessation
- 2000-10-11 KR KR1020000059816A patent/KR100722171B1/ko not_active Expired - Fee Related
- 2000-10-12 JP JP2000350288A patent/JP4806784B2/ja not_active Expired - Fee Related
- 2000-10-12 US US09/689,464 patent/US6569799B1/en not_active Expired - Lifetime
- 2000-10-12 CN CNB001344048A patent/CN1205238C/zh not_active Expired - Fee Related
-
2002
- 2002-05-23 US US10/154,631 patent/US6800705B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| US6800705B2 (en) | 2004-10-05 |
| EP1092731A1 (fr) | 2001-04-18 |
| FR2799468B1 (fr) | 2006-04-28 |
| JP4806784B2 (ja) | 2011-11-02 |
| EP1829901B1 (fr) | 2016-04-13 |
| ATE537196T1 (de) | 2011-12-15 |
| EP1829901A3 (fr) | 2007-10-10 |
| CA2321362A1 (fr) | 2001-04-12 |
| BR0004778B1 (pt) | 2010-11-30 |
| BR0004778A (pt) | 2001-05-29 |
| KR100722171B1 (ko) | 2007-05-29 |
| CN1310188A (zh) | 2001-08-29 |
| EP1829901A2 (fr) | 2007-09-05 |
| US6569799B1 (en) | 2003-05-27 |
| KR20010050962A (ko) | 2001-06-25 |
| CN1205238C (zh) | 2005-06-08 |
| FR2799468A1 (fr) | 2001-04-13 |
| JP2001294607A (ja) | 2001-10-23 |
| US20030004287A1 (en) | 2003-01-02 |
| EP1092731B1 (fr) | 2011-12-14 |
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