CN1711292A - 乙烯/丁二烯共聚物,用于合成其的催化体系和方法 - Google Patents
乙烯/丁二烯共聚物,用于合成其的催化体系和方法 Download PDFInfo
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- CN1711292A CN1711292A CNA2003801033661A CN200380103366A CN1711292A CN 1711292 A CN1711292 A CN 1711292A CN A2003801033661 A CNA2003801033661 A CN A2003801033661A CN 200380103366 A CN200380103366 A CN 200380103366A CN 1711292 A CN1711292 A CN 1711292A
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- Prior art keywords
- divinyl
- multipolymer
- equal
- ethene
- catalyst system
- Prior art date
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- KAKZBPTYRLMSJV-UHFFFAOYSA-N vinyl-ethylene Natural products C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 title claims abstract description 143
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 title claims abstract description 39
- 239000005977 Ethylene Substances 0.000 title claims abstract description 5
- 229920001577 copolymer Polymers 0.000 title abstract description 8
- 230000003197 catalytic effect Effects 0.000 title abstract description 6
- 230000015572 biosynthetic process Effects 0.000 title abstract description 4
- 238000003786 synthesis reaction Methods 0.000 title abstract 2
- 238000000034 method Methods 0.000 title description 5
- 125000002524 organometallic group Chemical group 0.000 claims abstract description 49
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims abstract description 27
- 239000003446 ligand Substances 0.000 claims abstract description 12
- 239000000203 mixture Substances 0.000 claims abstract description 11
- 229910052744 lithium Inorganic materials 0.000 claims abstract description 9
- 229910052782 aluminium Inorganic materials 0.000 claims abstract description 6
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 6
- 229910052747 lanthanoid Inorganic materials 0.000 claims abstract description 6
- 239000011777 magnesium Substances 0.000 claims abstract description 6
- 229910052749 magnesium Inorganic materials 0.000 claims abstract description 6
- 239000007818 Grignard reagent Substances 0.000 claims abstract description 5
- 150000004795 grignard reagents Chemical class 0.000 claims abstract description 5
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 39
- 239000003054 catalyst Substances 0.000 claims description 36
- 239000002904 solvent Substances 0.000 claims description 21
- 229910052779 Neodymium Inorganic materials 0.000 claims description 18
- QEFYFXOXNSNQGX-UHFFFAOYSA-N neodymium atom Chemical compound [Nd] QEFYFXOXNSNQGX-UHFFFAOYSA-N 0.000 claims description 18
- 238000006243 chemical reaction Methods 0.000 claims description 13
- -1 lanthanide metals Chemical class 0.000 claims description 12
- KXDANLFHGCWFRQ-UHFFFAOYSA-N magnesium;butane;octane Chemical compound [Mg+2].CCC[CH2-].CCCCCCC[CH2-] KXDANLFHGCWFRQ-UHFFFAOYSA-N 0.000 claims description 12
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 11
- 229910052751 metal Inorganic materials 0.000 claims description 10
- 239000002184 metal Substances 0.000 claims description 10
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 9
- 229910052799 carbon Inorganic materials 0.000 claims description 9
- 239000000460 chlorine Substances 0.000 claims description 9
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 7
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- QUXHCILOWRXCEO-UHFFFAOYSA-M magnesium;butane;chloride Chemical compound [Mg+2].[Cl-].CCC[CH2-] QUXHCILOWRXCEO-UHFFFAOYSA-M 0.000 claims description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-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
- 229910052794 bromium Inorganic materials 0.000 claims description 5
- 239000011737 fluorine Substances 0.000 claims description 5
- 229910052731 fluorine Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 5
- 230000002194 synthesizing effect Effects 0.000 claims description 4
- 238000010189 synthetic method Methods 0.000 claims description 3
- 239000004215 Carbon black (E152) Substances 0.000 claims description 2
- 229930195733 hydrocarbon Natural products 0.000 claims description 2
- 150000002430 hydrocarbons Chemical class 0.000 claims description 2
- 229910052710 silicon Inorganic materials 0.000 claims description 2
- 239000010703 silicon Substances 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- 239000000725 suspension Substances 0.000 claims description 2
- 150000001721 carbon Chemical group 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract description 4
- 239000003426 co-catalyst Substances 0.000 abstract 2
- 239000004411 aluminium Substances 0.000 abstract 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 abstract 1
- 238000005755 formation reaction Methods 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 150000002602 lanthanoids Chemical class 0.000 abstract 1
- 238000012360 testing method Methods 0.000 description 47
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 32
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 20
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 16
- 238000007334 copolymerization reaction Methods 0.000 description 15
- 230000000536 complexating effect Effects 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 11
- 238000001542 size-exclusion chromatography Methods 0.000 description 11
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 150000003839 salts Chemical class 0.000 description 9
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 8
- 238000001704 evaporation Methods 0.000 description 8
- 239000000047 product Substances 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 238000005481 NMR spectroscopy Methods 0.000 description 5
- 239000003643 water by type Substances 0.000 description 5
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- 239000004793 Polystyrene Substances 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- SIPUZPBQZHNSDW-UHFFFAOYSA-N diisobutylaluminium hydride Substances CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 4
- 238000000605 extraction Methods 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 230000010354 integration Effects 0.000 description 4
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 4
- 239000000178 monomer Substances 0.000 description 4
- 229920002223 polystyrene Polymers 0.000 description 4
- 238000001556 precipitation Methods 0.000 description 4
- 238000001816 cooling Methods 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 description 3
- 238000007872 degassing Methods 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 3
- 229910003002 lithium salt Inorganic materials 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- AZWXAPCAJCYGIA-UHFFFAOYSA-N bis(2-methylpropyl)alumane Chemical compound CC(C)C[AlH]CC(C)C AZWXAPCAJCYGIA-UHFFFAOYSA-N 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 230000009477 glass transition Effects 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 150000002642 lithium compounds Chemical class 0.000 description 2
- 159000000002 lithium salts Chemical class 0.000 description 2
- 229920002521 macromolecule Polymers 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 230000000630 rising effect Effects 0.000 description 2
- 238000005070 sampling Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 230000005526 G1 to G0 transition Effects 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 238000011000 absolute method Methods 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 238000011208 chromatographic data Methods 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 125000001475 halogen functional group Chemical group 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- CPOFMOWDMVWCLF-UHFFFAOYSA-N methyl(oxo)alumane Chemical compound C[Al]=O CPOFMOWDMVWCLF-UHFFFAOYSA-N 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 125000002097 pentamethylcyclopentadienyl group Chemical group 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 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
- 230000008961 swelling Effects 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical class CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- ZWYDDDAMNQQZHD-UHFFFAOYSA-L titanium(ii) chloride Chemical compound [Cl-].[Cl-].[Ti+2] ZWYDDDAMNQQZHD-UHFFFAOYSA-L 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000005406 washing 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
- C08F210/00—Copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
- C08F210/04—Monomers containing three or four carbon atoms
- C08F210/08—Butenes
- C08F210/10—Isobutene
- C08F210/12—Isobutene with conjugated diolefins, e.g. butyl rubber
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F10/00—Homopolymers and copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- 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
- 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
- C08F236/06—Butadiene
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Polymerization Catalysts (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
Description
试验 | x(mg) | 助催化剂和(助催化剂/钕)比例 | m(g) | t(min) | y(%)单体中的丁二烯 | |
No.1 | 39.5 | BOMAG(2/1) | 12.7 | 420 | 20 | |
No.2 | 33.6 | BOMAG(2/1) | 9.2 | 180 | 30 | |
试验 | τ(%)共聚物中的丁二烯 | Tg(℃) | 丁二烯插入 | Mn(g/mol)/Ip | ||
%1,2 | %反式-1,4 | %反式-1,2环己烷 | ||||
No.1 | 13.1 | -31.2 | 27.2 | 20.4 | 52.4 | 147,500/3.1 |
No.2 | 15.0 | -34.0 | 22.9 | 25.8 | 51.3 | 127,700/3.0 |
试验 | x(mg) | 助催化剂和(助催化剂/钕)比例 | m(g) | t(min) | y(%)单体中的丁二烯 | |
No.3 | 23.1 | BuMgCl(20/1) | 4.2 | 60 | 20 | |
No.4 | 39.7 | BOMAG(20/1) | 13.2 | 180 | 20 | |
试验 | τ(%)共聚物中的丁二烯 | Tg(℃) | 丁二烯插入 | Mn(g/mol)/Ip | ||
%1,2 | %反式-1,4 | %反式-1,2环己烷 | ||||
No.3 | 11.8 | 未测量 | 19.4 | 23.0 | 57.6 | 10,000/1.2 |
No.4 | 11.0 | -28.5 | 21.8 | 24.6 | 53.5 | 7,800/1.5 |
试验 | x(mg) | 丁二烯的质量z(g) | P(巴) | T(℃) | m(g) | t(min) | ||
No.5 | 44.9 | 16 | 20 | 80 | 21.7 | 60 | ||
No.6 | 47.2 | 18 | 10 | 80 | 15.8 | 150 | ||
No.7 | 46.3 | 7 | 10 | 80 | 11.4 | 60 | ||
No.8 | 22.0 | 8 | 10 | 80 | 5.9 | 180 | ||
No.9 | 40.6 | 10 | 10 | 60 | 15.8 | 150 | ||
试验 | τ(%)共聚物中的丁二烯 | Tg(℃) | 丁二烯插入 | Mn(g/mol)/Ip | ||||
%1,2 | %反式-1,4 | %反式-1,2环己烷 | ||||||
No.5 | 20.4 | -43.8 | 55.0 | 25.0 | 20.0 | 260,000/1.8 | ||
No.6 | 30.4 | -45.8 | 53.5 | 27.8 | 18.7 | 70,700/2.0 | ||
No.7 | 19.7 | -42.8 | 45.5 | 25.2 | 29.3 | 73,200/1.9 | ||
No.8 | 20.0 | -43.2 | 44.5 | 26.7 | 28.8 | 378,600/2.8 | ||
No.9 | 23.6 | -47.6 | 57.0 | 22.7 | 20.3 | 801,450/1.9 |
试验 | x(mg) | (BuLi/DiBAH/钕)比例 | P(巴) | T(℃) | m(g) | t(min) |
No.10 | 30 | 10/10/1 | 4 | 80 | 4.8 | 120 |
No.11 | 31 | 10/10/1 | 4 | 60 | 2.1 | 60 |
试验 | y(%)单体 | τ(%)共聚物中 | 丁二烯插入 | Mn |
中的丁二烯 | 的丁二烯 | %1,2 | %反式-1,4 | (g/mol)/Ip | |
No.10 | 43.0 | 41.0 | 2.5 | 97.5 | 6,900/2.2 |
No.11 | 40.0 | 37.5 | 2.5 | 97.5 | 10,530/1.8 |
试验 | x(mg) | (助催化剂/钕)比例 | P(巴) | T(℃) | m(g) | t(min) | |
No.12 | 55 | 2/1 | 4 | 60 | 2.3 | 240 | |
试验 | y(%)单体中的丁二烯 | τ(%)共聚物中的丁二烯 | 丁二烯插入 | Mn(g/mol)/Ip | |||
%1,2 | %反式-1,4 | ||||||
No.12 | 40.0 | 40.2 | 2.3 | 97.7 | 44,600/1.8 |
Claims (23)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR0212893 | 2002-10-16 | ||
FR02/12893 | 2002-10-16 |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CNA2007100042409A Division CN101045770A (zh) | 2002-10-16 | 2003-10-13 | 用于合成乙烯和丁二烯共聚物的催化体系 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN1711292A true CN1711292A (zh) | 2005-12-21 |
CN100523023C CN100523023C (zh) | 2009-08-05 |
Family
ID=32104296
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CNA2007100042409A Pending CN101045770A (zh) | 2002-10-16 | 2003-10-13 | 用于合成乙烯和丁二烯共聚物的催化体系 |
CNB2003801033661A Expired - Lifetime CN100523023C (zh) | 2002-10-16 | 2003-10-13 | 乙烯/丁二烯共聚物,用于合成其的催化体系和方法 |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CNA2007100042409A Pending CN101045770A (zh) | 2002-10-16 | 2003-10-13 | 用于合成乙烯和丁二烯共聚物的催化体系 |
Country Status (10)
Country | Link |
---|---|
US (1) | US7094854B2 (zh) |
EP (1) | EP1554321B1 (zh) |
JP (1) | JP5301073B2 (zh) |
KR (1) | KR20050101157A (zh) |
CN (2) | CN101045770A (zh) |
AU (1) | AU2003286138A1 (zh) |
BR (1) | BR0315380A (zh) |
CA (1) | CA2502345A1 (zh) |
RU (1) | RU2312870C2 (zh) |
WO (1) | WO2004035639A1 (zh) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN108699171A (zh) * | 2015-12-08 | 2018-10-23 | 米其林集团总公司 | 1,3-二烯与乙烯或α-单烯烃的单官能或遥爪共聚物 |
CN108699187A (zh) * | 2015-12-08 | 2018-10-23 | 米其林集团总公司 | 1,3-丁二烯和乙烯的单官能或遥爪共聚物 |
CN111212860A (zh) * | 2017-10-19 | 2020-05-29 | 米其林集团总公司 | 具有二烯单元和单烯烃单元的嵌段聚合物 |
CN111819209A (zh) * | 2018-03-05 | 2020-10-23 | 株式会社普利司通 | 共聚物、共聚物的制造方法、橡胶组合物以及轮胎 |
Families Citing this family (140)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
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 |
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 |
FR2893030B1 (fr) * | 2006-10-17 | 2011-04-15 | Michelin Soc Tech | Copolymere ethylene/butadiene |
WO2011016210A1 (ja) | 2009-08-07 | 2011-02-10 | 株式会社ブリヂストン | 共重合体の製造方法 |
FR2957601B1 (fr) | 2010-03-18 | 2012-03-16 | Michelin Soc Tech | Pneumatique et composition de caoutchouc contenant un polymere greffe |
FR2962733B1 (fr) | 2010-07-13 | 2012-08-17 | Michelin Soc Tech | Polymere greffe par des molecules associatives azotees. |
FR2962729B1 (fr) | 2010-07-13 | 2012-09-21 | Arkema France | Molecules porteuses de groupes associatifs |
FR2962732B1 (fr) | 2010-07-13 | 2012-08-17 | Michelin Soc Tech | Polymere greffe par des molecules associatives azotees |
FR2962737B1 (fr) | 2010-07-13 | 2012-08-17 | Michelin Soc Tech | Composition de caoutchouc contenant un elastomere modifie, son procede de preparation et pneumatique la contenant |
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CN108699187A (zh) * | 2015-12-08 | 2018-10-23 | 米其林集团总公司 | 1,3-丁二烯和乙烯的单官能或遥爪共聚物 |
CN108699187B (zh) * | 2015-12-08 | 2020-12-22 | 米其林集团总公司 | 1,3-丁二烯和乙烯的单官能或遥爪共聚物 |
CN108699171B (zh) * | 2015-12-08 | 2021-09-03 | 米其林集团总公司 | 1,3-二烯与乙烯或α-单烯烃的单官能或遥爪共聚物 |
CN111212860A (zh) * | 2017-10-19 | 2020-05-29 | 米其林集团总公司 | 具有二烯单元和单烯烃单元的嵌段聚合物 |
CN111819209A (zh) * | 2018-03-05 | 2020-10-23 | 株式会社普利司通 | 共聚物、共聚物的制造方法、橡胶组合物以及轮胎 |
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KR20050101157A (ko) | 2005-10-20 |
BR0315380A (pt) | 2005-08-23 |
WO2004035639A1 (fr) | 2004-04-29 |
CA2502345A1 (fr) | 2004-04-29 |
US7094854B2 (en) | 2006-08-22 |
RU2005114520A (ru) | 2005-11-10 |
US20050239639A1 (en) | 2005-10-27 |
AU2003286138A1 (en) | 2004-05-04 |
JP5301073B2 (ja) | 2013-09-25 |
CN100523023C (zh) | 2009-08-05 |
RU2312870C2 (ru) | 2007-12-20 |
JP2006503141A (ja) | 2006-01-26 |
CN101045770A (zh) | 2007-10-03 |
EP1554321A1 (fr) | 2005-07-20 |
AU2003286138A8 (en) | 2004-05-04 |
EP1554321B1 (fr) | 2014-06-04 |
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