CA1212932A - Polymerisation of conjugated dienes - Google Patents
Polymerisation of conjugated dienesInfo
- Publication number
- CA1212932A CA1212932A CA000424869A CA424869A CA1212932A CA 1212932 A CA1212932 A CA 1212932A CA 000424869 A CA000424869 A CA 000424869A CA 424869 A CA424869 A CA 424869A CA 1212932 A CA1212932 A CA 1212932A
- Authority
- CA
- Canada
- Prior art keywords
- catalyst
- component
- conjugated diene
- polymerisation
- content
- 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
- 150000001993 dienes Chemical class 0.000 title claims abstract description 38
- 239000003054 catalyst Substances 0.000 claims abstract description 37
- 229910052761 rare earth metal Inorganic materials 0.000 claims abstract description 19
- 150000001875 compounds Chemical class 0.000 claims abstract description 17
- 239000002841 Lewis acid Substances 0.000 claims abstract description 11
- 150000007517 lewis acids Chemical class 0.000 claims abstract description 11
- 229920002554 vinyl polymer Polymers 0.000 claims description 14
- 229910052744 lithium Inorganic materials 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 11
- 239000000178 monomer Substances 0.000 claims description 9
- 229910052779 Neodymium Inorganic materials 0.000 claims description 8
- QEFYFXOXNSNQGX-UHFFFAOYSA-N neodymium atom Chemical compound [Nd] QEFYFXOXNSNQGX-UHFFFAOYSA-N 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 7
- -1 praeseodymium Chemical compound 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 3
- 229910052684 Cerium Inorganic materials 0.000 claims description 3
- 229910052692 Dysprosium Inorganic materials 0.000 claims description 3
- 229910052688 Gadolinium Inorganic materials 0.000 claims description 3
- 229910052771 Terbium Inorganic materials 0.000 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- ZMIGMASIKSOYAM-UHFFFAOYSA-N cerium Chemical compound [Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce] ZMIGMASIKSOYAM-UHFFFAOYSA-N 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- KBQHZAAAGSGFKK-UHFFFAOYSA-N dysprosium atom Chemical compound [Dy] KBQHZAAAGSGFKK-UHFFFAOYSA-N 0.000 claims description 3
- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 claims description 3
- 229910052746 lanthanum Inorganic materials 0.000 claims description 3
- FZLIPJUXYLNCLC-UHFFFAOYSA-N lanthanum atom Chemical compound [La] FZLIPJUXYLNCLC-UHFFFAOYSA-N 0.000 claims description 3
- 150000002681 magnesium compounds Chemical class 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- GZCRRIHWUXGPOV-UHFFFAOYSA-N terbium atom Chemical compound [Tb] GZCRRIHWUXGPOV-UHFFFAOYSA-N 0.000 claims description 3
- 229910052693 Europium Inorganic materials 0.000 claims description 2
- 229910052765 Lutetium Inorganic materials 0.000 claims description 2
- 229910052772 Samarium Inorganic materials 0.000 claims description 2
- OGPBJKLSAFTDLK-UHFFFAOYSA-N europium atom Chemical compound [Eu] OGPBJKLSAFTDLK-UHFFFAOYSA-N 0.000 claims description 2
- OHSVLFRHMCKCQY-UHFFFAOYSA-N lutetium atom Chemical compound [Lu] OHSVLFRHMCKCQY-UHFFFAOYSA-N 0.000 claims description 2
- KZUNJOHGWZRPMI-UHFFFAOYSA-N samarium atom Chemical compound [Sm] KZUNJOHGWZRPMI-UHFFFAOYSA-N 0.000 claims description 2
- 229910052691 Erbium Inorganic materials 0.000 claims 1
- 229910052689 Holmium Inorganic materials 0.000 claims 1
- 229910052773 Promethium Inorganic materials 0.000 claims 1
- 229910052769 Ytterbium Inorganic materials 0.000 claims 1
- 229920001400 block copolymer Polymers 0.000 claims 1
- UYAHIZSMUZPPFV-UHFFFAOYSA-N erbium Chemical compound [Er] UYAHIZSMUZPPFV-UHFFFAOYSA-N 0.000 claims 1
- KJZYNXUDTRRSPN-UHFFFAOYSA-N holmium atom Chemical compound [Ho] KJZYNXUDTRRSPN-UHFFFAOYSA-N 0.000 claims 1
- VQMWBBYLQSCNPO-UHFFFAOYSA-N promethium atom Chemical compound [Pm] VQMWBBYLQSCNPO-UHFFFAOYSA-N 0.000 claims 1
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 claims 1
- 229920000642 polymer Polymers 0.000 abstract description 35
- 238000006243 chemical reaction Methods 0.000 abstract description 26
- 150000002901 organomagnesium compounds Chemical class 0.000 abstract description 7
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 26
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 11
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 229910000722 Didymium Inorganic materials 0.000 description 8
- 241000224487 Didymium Species 0.000 description 8
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- 239000000047 product Substances 0.000 description 7
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
- 239000004411 aluminium Substances 0.000 description 6
- 229910052782 aluminium Inorganic materials 0.000 description 6
- 229920001519 homopolymer Polymers 0.000 description 6
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 5
- MGDOJPNDRJNJBK-UHFFFAOYSA-N ethylaluminum Chemical compound [Al].C[CH2] MGDOJPNDRJNJBK-UHFFFAOYSA-N 0.000 description 5
- 239000011777 magnesium Substances 0.000 description 5
- 229910052749 magnesium Inorganic materials 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 150000002910 rare earth metals Chemical class 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- 239000004215 Carbon black (E152) Substances 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- 150000002430 hydrocarbons Chemical class 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
- KJJBSBKRXUVBMX-UHFFFAOYSA-N magnesium;butane Chemical compound [Mg+2].CCC[CH2-].CCC[CH2-] KJJBSBKRXUVBMX-UHFFFAOYSA-N 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- 239000005062 Polybutadiene Substances 0.000 description 2
- 229910052777 Praseodymium Inorganic materials 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000004703 alkoxides Chemical class 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical compound C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 229910052747 lanthanoid Inorganic materials 0.000 description 2
- 150000002899 organoaluminium compounds Chemical class 0.000 description 2
- 229920002857 polybutadiene Polymers 0.000 description 2
- PUDIUYLPXJFUGB-UHFFFAOYSA-N praseodymium atom Chemical compound [Pr] PUDIUYLPXJFUGB-UHFFFAOYSA-N 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 229920003048 styrene butadiene rubber Polymers 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 1
- YRAJNWYBUCUFBD-UHFFFAOYSA-N 2,2,6,6-tetramethylheptane-3,5-dione Chemical compound CC(C)(C)C(=O)CC(=O)C(C)(C)C YRAJNWYBUCUFBD-UHFFFAOYSA-N 0.000 description 1
- JHUUPUMBZGWODW-UHFFFAOYSA-N 3,6-dihydro-1,2-dioxine Chemical compound C1OOCC=C1 JHUUPUMBZGWODW-UHFFFAOYSA-N 0.000 description 1
- VXEGSRKPIUDPQT-UHFFFAOYSA-N 4-[4-(4-methoxyphenyl)piperazin-1-yl]aniline Chemical compound C1=CC(OC)=CC=C1N1CCN(C=2C=CC(N)=CC=2)CC1 VXEGSRKPIUDPQT-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- OAOABCKPVCUNKO-UHFFFAOYSA-N 8-methyl Nonanoic acid Chemical compound CC(C)CCCCCCC(O)=O OAOABCKPVCUNKO-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 239000007818 Grignard reagent Substances 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
- 239000002879 Lewis base Substances 0.000 description 1
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- PQLAYKMGZDUDLQ-UHFFFAOYSA-K aluminium bromide Chemical compound Br[Al](Br)Br PQLAYKMGZDUDLQ-UHFFFAOYSA-K 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 150000004796 dialkyl magnesium compounds Chemical class 0.000 description 1
- YNLAOSYQHBDIKW-UHFFFAOYSA-M diethylaluminium chloride Chemical compound CC[Al](Cl)CC YNLAOSYQHBDIKW-UHFFFAOYSA-M 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 125000005594 diketone group Chemical group 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- UAIZDWNSWGTKFZ-UHFFFAOYSA-L ethylaluminum(2+);dichloride Chemical compound CC[Al](Cl)Cl UAIZDWNSWGTKFZ-UHFFFAOYSA-L 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 150000004795 grignard reagents Chemical class 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229920005669 high impact polystyrene Polymers 0.000 description 1
- 239000004797 high-impact polystyrene Substances 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 229910052740 iodine Chemical group 0.000 description 1
- 239000011630 iodine Chemical group 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 150000002602 lanthanoids Chemical class 0.000 description 1
- 150000007527 lewis bases Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- JLUFWMXJHAVVNN-UHFFFAOYSA-N methyltrichlorosilane Chemical compound C[Si](Cl)(Cl)Cl JLUFWMXJHAVVNN-UHFFFAOYSA-N 0.000 description 1
- 150000002763 monocarboxylic acids Chemical class 0.000 description 1
- UJQMLHKSZKBMMO-UHFFFAOYSA-N n,n-diethylethanamine;pyridine Chemical compound C1=CC=NC=C1.CCN(CC)CC UJQMLHKSZKBMMO-UHFFFAOYSA-N 0.000 description 1
- 150000002896 organic halogen compounds Chemical class 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920001195 polyisoprene Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- BTHKKGNFNRSFSR-UHFFFAOYSA-N praseodymium 2,2,6,6-tetramethylheptane-3,5-dione Chemical compound CC(C)(C(CC(C(C)(C)C)=O)=O)C.[Pr] BTHKKGNFNRSFSR-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 239000005049 silicon tetrachloride Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229920003051 synthetic elastomer Polymers 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- WTQUHLHXFJEOTI-UHFFFAOYSA-H trichloroneodymium;trichloropraseodymium Chemical compound Cl[Pr](Cl)Cl.Cl[Nd](Cl)Cl WTQUHLHXFJEOTI-UHFFFAOYSA-H 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
- C08F36/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds
- C08F36/02—Homopolymers and 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
- C08F36/04—Homopolymers and 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
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)
- Polymerization Catalysts (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8209712 | 1982-04-01 | ||
| GB8209712 | 1982-04-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1212932A true CA1212932A (en) | 1986-10-21 |
Family
ID=10529476
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000424869A Expired CA1212932A (en) | 1982-04-01 | 1983-03-30 | Polymerisation of conjugated dienes |
Country Status (6)
| Country | Link |
|---|---|
| US (2) | US4619982A (OSRAM) |
| EP (1) | EP0091287B1 (OSRAM) |
| JP (1) | JPS591508A (OSRAM) |
| CA (1) | CA1212932A (OSRAM) |
| DE (1) | DE3373661D1 (OSRAM) |
| GB (1) | GB2118199B (OSRAM) |
Families Citing this family (50)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8314382D0 (en) * | 1983-05-24 | 1983-06-29 | Enoxy Chemicals Ltd | Polymerisation of conjugated dienes |
| FR2567135B1 (fr) * | 1984-07-03 | 1989-01-13 | Asahi Chemical Ind | Polymere ou copolymere de butadiene et procede de preparation |
| ES2087057T3 (es) * | 1986-02-20 | 1996-07-16 | Asahi Chemical Ind | Copolimero bloque cristalino y procedimiento para su fabricacion. |
| EP0304088B1 (en) * | 1987-08-19 | 1993-01-27 | Asahi Kasei Kogyo Kabushiki Kaisha | A prepolymerization process for producing a conjugated diene compound prepolymer solution |
| US5134199A (en) * | 1987-11-27 | 1992-07-28 | Asahi Kasei Kogyo Kabushiki Kaisha | Diene block polymer and polymer composition |
| CA2035650C (en) * | 1990-02-14 | 1997-02-25 | Hajime Yasuda | Process of preparing polymer or copolymer of unsaturated carboxylic acid ester |
| US5218064A (en) * | 1990-02-14 | 1993-06-08 | Showa Denko K.K. | Process for preparing narrow molecular weight distribution syndiotactic polymers or copolymers of unsaturated carboxylic acid esters |
| US5223579A (en) * | 1991-01-28 | 1993-06-29 | Shell Oil Company | Solid viscosity index improvers which provide excellant low temperature viscosity |
| DE4334045A1 (de) * | 1993-10-06 | 1995-04-13 | Bayer Ag | Katalysator, dessen Herstellung und Verwendung zur Gasphasenpolymerisation von konjugierten Dienen |
| IT1273753B (it) * | 1994-02-11 | 1997-07-10 | Eniriceche Spa | Sistema catalitico e processo per la produzione di polidiolefine |
| DE19512127A1 (de) * | 1995-04-04 | 1996-10-10 | Bayer Ag | Neuer Katalysator für die Gasphasenpolymerisation von konjugierten Dienen |
| US5914377A (en) * | 1995-04-04 | 1999-06-22 | Bayer Ag | Method for the production of diene rubbers in the gas phase |
| DE19512116A1 (de) * | 1995-04-04 | 1996-10-10 | Bayer Ag | Gasphasenpolymerisation von konjugierten Dienen in Gegenwart von Allylverbindungen der seltenen Erden |
| NL1007534C2 (nl) * | 1996-12-03 | 1999-05-12 | Japan Elastomer Co | Rubberachtig polymeer alsmede werkwijze voor de bereiding daarvan. |
| RU2129566C1 (ru) * | 1997-07-15 | 1999-04-27 | Институт нефтехимического синтеза им.А.В.Топчиева РАН | Способ получения смесей цис- и транс-полимеров сопряженных диенов |
| US6018007A (en) * | 1997-09-22 | 2000-01-25 | Bridgestone Corporation | Synthesis of 1,4-trans-polybutadiene using a lanthanide organic acid salt catalyst |
| US6197713B1 (en) * | 1997-12-19 | 2001-03-06 | Bridgestone Corporation | Use of Lewis acids for the breakdown of gelatinous rare earth compounds in hydrocarbon solutions |
| US6177603B1 (en) * | 1998-06-12 | 2001-01-23 | Bridgestone Corporation | Organo zinc and rare earth catalyst system in the polymerization of conjugated dienes |
| US6767927B1 (en) * | 1999-04-26 | 2004-07-27 | Rhodia Rare Earths Inc. | Synthesis of stable solutions of rare earth tris (organophosphate) in hydrocarbon solvents |
| WO2001077199A1 (fr) * | 2000-04-07 | 2001-10-18 | Riken | Composition catalytique et procede de production de copolymere |
| DE10022497A1 (de) | 2000-05-09 | 2001-11-15 | Bayer Ag | Copolymerisation konjugierter Diene mit nichtkonjugierten Olefinen mittels Katalysatoren der Seltenen Erden |
| WO2001087991A1 (en) * | 2000-05-17 | 2001-11-22 | Basell Technology Company B.V. | Component of catalyst for the diene polymerization, catalyst obtained therefrom and process for the preparation of polydienes based on it |
| US6433105B1 (en) | 2000-06-09 | 2002-08-13 | Bridgestone Corporation | Process for desolventizing low molecular weight diene polymers |
| DE60213380T2 (de) * | 2001-02-28 | 2007-08-23 | Bridgestone Corp. | Kontinuierliches verfahren zur herstellung von engeren molekulargewichtverteilungen konjugierten dien-polymeren und dadurch hergestellten produkten |
| FR2824834B1 (fr) * | 2001-05-18 | 2005-05-13 | Rhodia Elect & Catalysis | Procede de preparation de copolymeres blocs, copolymeres blocs ainsi obtenus et utilisation comme agents compatibilisants |
| BR0213639A (pt) * | 2001-10-12 | 2004-09-14 | Dow Global Technologies Inc | Composições de complexos metálicos e seu uso como catalisadores para produzir polidienos |
| CA2516232C (en) * | 2003-02-21 | 2013-05-14 | Dow Global Technologies Inc. | Process for homo- or copolymerization of conjugated olefines |
| JP4983015B2 (ja) * | 2005-12-15 | 2012-07-25 | 宇部興産株式会社 | 共役ジエン重合体の製造方法 |
| CN101610917B (zh) * | 2006-12-19 | 2012-10-10 | 思迪隆欧洲有限公司 | 硫化物改性的弹性体聚合物 |
| HUE029872T2 (en) * | 2008-06-06 | 2017-04-28 | Trinseo Europe Gmbh | Modified elastomeric polymers |
| CN102216335B (zh) * | 2008-11-11 | 2014-01-29 | 思迪隆欧洲有限公司 | 从改性聚合物的制备中除去硅烷醇的方法 |
| EP2516474B9 (en) | 2009-12-21 | 2015-04-08 | Styron Europe GmbH | Modified polymer compositions |
| PL2516478T3 (pl) | 2009-12-21 | 2014-11-28 | Trinseo Europe Gmbh | Modyfikowane kompozycje polimerowe |
| WO2012041804A2 (en) | 2010-09-30 | 2012-04-05 | Styron Europe Gmbh | Polymer compositions |
| KR101975074B1 (ko) | 2012-02-27 | 2019-05-03 | 가부시키가이샤 브리지스톤 | 고-시스 폴리디엔들의 제조 방법들 |
| KR101959602B1 (ko) | 2012-09-14 | 2019-03-18 | 트린세오 유럽 게엠베하 | 아미노 실란-개질된 중합체 |
| JP6359246B2 (ja) * | 2013-06-11 | 2018-07-18 | 宇部興産株式会社 | プラセオジム化合物およびその製造方法 |
| JP6619923B2 (ja) * | 2013-06-11 | 2019-12-11 | 宇部興産株式会社 | 共役ジエン重合用触媒、それを用いた共役ジエン重合体の製造方法、及び共役ジエン重合体 |
| KR20160033105A (ko) | 2013-07-22 | 2016-03-25 | 트린세오 유럽 게엠베하 | 중합 개시제 |
| US10035908B1 (en) | 2013-12-03 | 2018-07-31 | Bridgestone Corporation | Process for preparing blends of trans-1,4-polybutadiene and syndiotactic 1,2-polybutadiene |
| CN105814132A (zh) | 2013-12-03 | 2016-07-27 | 株式会社普利司通 | 用于制备顺式-1，4-聚丁二烯和间同立构1，2-聚丁二烯的共混物的方法 |
| JP6665779B2 (ja) * | 2014-07-09 | 2020-03-13 | 宇部興産株式会社 | 共役ジエン重合用触媒、共役ジエン重合体、変性共役ジエン重合体、及びポリブタジエン、並びに、それらを含む組成物 |
| EP3169712B1 (en) | 2014-07-14 | 2018-10-10 | Trinseo Europe GmbH | Aminosilyl-substituted diarylethene compounds for anionic polymerisation |
| JPWO2016039003A1 (ja) * | 2014-09-12 | 2017-06-22 | 宇部興産株式会社 | ゴム組成物 |
| PL3045495T3 (pl) | 2015-01-14 | 2017-10-31 | Trinseo Europe Gmbh | Funkcjonalizowane kompozycje polimerów elastomerowych, sposoby ich przygotowywania oraz ich usieciowane kompozycje kauczukowe |
| EP3133093A1 (en) | 2015-08-20 | 2017-02-22 | Trinseo Europe GmbH | Elastomeric polymer |
| EP3363804A1 (en) | 2017-02-20 | 2018-08-22 | Trinseo Europe GmbH | Metallated benzylsilanes and their use as polymerization initiators |
| FR3123917B1 (fr) | 2021-06-10 | 2024-04-19 | Michelin & Cie | Système catalytique pour la polymérisation stéréospécifique de diènes et leur utilisation en procédé de synthèse de polymères diéniques |
| FR3123916B1 (fr) | 2021-06-10 | 2024-10-04 | Michelin & Cie | Système catalytique pour la polymérisation stéréospécifique de diènes et leur utilisation en procédé de synthèse de polymères diéniques |
| FR3123918B1 (fr) | 2021-06-10 | 2024-03-22 | Michelin & Cie | Système catalytique pour la polymérisation stéréospécifique de diènes et leur utilisation en procédé de synthèse de polymères diéniques |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1016022B (de) * | 1954-01-19 | 1957-09-19 | Dr Dr E H Karl Ziegler | Verfahren zur Herstellung von hochmolekularen Polyaethylenen |
| US2953531A (en) * | 1954-08-16 | 1960-09-20 | Du Pont | Cerium polymerization catalysts |
| US3118864A (en) * | 1954-08-16 | 1964-01-21 | Du Pont | Process of polymerizing conjugated alkadienes |
| US2921060A (en) * | 1956-07-12 | 1960-01-12 | Sun Oil Co | Polymerization of ethylene with a cerium acetylacetonate-metal alkyl catalyst |
| GB865248A (en) * | 1956-12-28 | 1961-04-12 | Hoechst Ag | Process for the polymerisation of olefines |
| US3151104A (en) * | 1958-05-22 | 1964-09-29 | Du Pont | Polymers of propadiene |
| DE1251535B (de) * | 1965-05-04 | 1967-10-05 | Badische Anilin £x Soda-Fabrik Aktiengesellschaft Ludwigshafen/Rhem | Verfahren zur Herstellung von Butadienpolymensaten |
| US3644585A (en) * | 1967-12-19 | 1972-02-22 | Ube Industries | Process for the preparation of polybutadiene |
| GB1294725A (en) * | 1969-03-27 | 1972-11-01 | Goodyear Tire & Rubber | Polymerization of diolefins |
| IT1085663B (it) * | 1977-08-01 | 1985-05-28 | Snam Progetti | Procedimento per la polimerizzazione e copolimerizzazione di diolefine e mezzi adatti allo scopo |
| DE2830080A1 (de) * | 1978-07-08 | 1980-01-17 | Bayer Ag | Katalysator, dessen herstellung und verwendung zur loesungspolymerisation von butadien |
| GB8314382D0 (en) * | 1983-05-24 | 1983-06-29 | Enoxy Chemicals Ltd | Polymerisation of conjugated dienes |
-
1983
- 1983-03-30 CA CA000424869A patent/CA1212932A/en not_active Expired
- 1983-03-31 DE DE8383301839T patent/DE3373661D1/de not_active Expired
- 1983-03-31 EP EP83301839A patent/EP0091287B1/en not_active Expired
- 1983-03-31 US US06/480,806 patent/US4619982A/en not_active Expired - Lifetime
- 1983-03-31 GB GB08309061A patent/GB2118199B/en not_active Expired
- 1983-04-01 JP JP58057726A patent/JPS591508A/ja active Granted
-
1986
- 1986-08-04 US US06/892,821 patent/US4689368A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| EP0091287B1 (en) | 1987-09-16 |
| DE3373661D1 (en) | 1987-10-22 |
| GB2118199A (en) | 1983-10-26 |
| JPS591508A (ja) | 1984-01-06 |
| JPH033683B2 (OSRAM) | 1991-01-21 |
| GB2118199B (en) | 1985-07-10 |
| EP0091287A3 (en) | 1984-02-22 |
| GB8309061D0 (en) | 1983-05-11 |
| US4619982A (en) | 1986-10-28 |
| US4689368A (en) | 1987-08-25 |
| EP0091287A2 (en) | 1983-10-12 |
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