GB1061002A - Polymerization catalyst and use thereof - Google Patents
Polymerization catalyst and use thereofInfo
- Publication number
- GB1061002A GB1061002A GB5595/64A GB559564A GB1061002A GB 1061002 A GB1061002 A GB 1061002A GB 5595/64 A GB5595/64 A GB 5595/64A GB 559564 A GB559564 A GB 559564A GB 1061002 A GB1061002 A GB 1061002A
- Authority
- GB
- United Kingdom
- Prior art keywords
- cerous
- chloride
- triisobutyl
- metal
- acid
- 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
- 239000002685 polymerization catalyst Substances 0.000 title abstract 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract 8
- -1 alkamino Chemical group 0.000 abstract 8
- 229910052751 metal Inorganic materials 0.000 abstract 8
- 239000002184 metal Substances 0.000 abstract 8
- 125000004432 carbon atom Chemical group C* 0.000 abstract 5
- 239000003054 catalyst Substances 0.000 abstract 4
- 150000001875 compounds Chemical class 0.000 abstract 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 3
- 229910052684 Cerium Inorganic materials 0.000 abstract 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 abstract 3
- 239000013522 chelant Substances 0.000 abstract 3
- UWNADWZGEHDQAB-UHFFFAOYSA-N 2,5-dimethylhexane Chemical group CC(C)CCC(C)C UWNADWZGEHDQAB-UHFFFAOYSA-N 0.000 abstract 2
- WZUODJNEIXSNEU-UHFFFAOYSA-N 2-Hydroxy-4-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C(O)=C1 WZUODJNEIXSNEU-UHFFFAOYSA-N 0.000 abstract 2
- NAGSWLQWNWNACQ-UHFFFAOYSA-N 2-[(2-methylpropan-2-yl)oxy]benzaldehyde Chemical compound CC(C)(C)OC1=CC=CC=C1C=O NAGSWLQWNWNACQ-UHFFFAOYSA-N 0.000 abstract 2
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 abstract 2
- 229910004664 Cerium(III) chloride Inorganic materials 0.000 abstract 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 abstract 2
- MOWSRKKNBYKPGK-UHFFFAOYSA-N OC1=CC=C(C2CCCCC2)C=C1C=O.Cl Chemical compound OC1=CC=C(C2CCCCC2)C=C1C=O.Cl MOWSRKKNBYKPGK-UHFFFAOYSA-N 0.000 abstract 2
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 abstract 2
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 abstract 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 2
- 229910052782 aluminium Inorganic materials 0.000 abstract 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 abstract 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 abstract 2
- VYLVYHXQOHJDJL-UHFFFAOYSA-K cerium trichloride Chemical compound Cl[Ce](Cl)Cl VYLVYHXQOHJDJL-UHFFFAOYSA-K 0.000 abstract 2
- GGVUYAXGAOIFIC-UHFFFAOYSA-K cerium(3+);2-ethylhexanoate Chemical compound [Ce+3].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O GGVUYAXGAOIFIC-UHFFFAOYSA-K 0.000 abstract 2
- 150000001993 dienes Chemical class 0.000 abstract 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 abstract 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 abstract 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 abstract 2
- 125000000524 functional group Chemical group 0.000 abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 2
- 150000002500 ions Chemical class 0.000 abstract 2
- 229910021645 metal ion Inorganic materials 0.000 abstract 2
- 229910052757 nitrogen Inorganic materials 0.000 abstract 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 abstract 2
- 239000013110 organic ligand Substances 0.000 abstract 2
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 abstract 2
- 230000000737 periodic effect Effects 0.000 abstract 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 abstract 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 2
- SMQUZDBALVYZAC-UHFFFAOYSA-N salicylaldehyde Chemical compound OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 abstract 2
- MCULRUJILOGHCJ-UHFFFAOYSA-N triisobutylaluminium Chemical compound CC(C)C[Al](CC(C)C)CC(C)C MCULRUJILOGHCJ-UHFFFAOYSA-N 0.000 abstract 2
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 abstract 2
- HFVMEOPYDLEHBR-UHFFFAOYSA-N (2-fluorophenyl)-phenylmethanol Chemical compound C=1C=CC=C(F)C=1C(O)C1=CC=CC=C1 HFVMEOPYDLEHBR-UHFFFAOYSA-N 0.000 abstract 1
- OBETXYAYXDNJHR-SSDOTTSWSA-M (2r)-2-ethylhexanoate Chemical compound CCCC[C@@H](CC)C([O-])=O OBETXYAYXDNJHR-SSDOTTSWSA-M 0.000 abstract 1
- CVBUKMMMRLOKQR-UHFFFAOYSA-N 1-phenylbutane-1,3-dione Chemical compound CC(=O)CC(=O)C1=CC=CC=C1 CVBUKMMMRLOKQR-UHFFFAOYSA-N 0.000 abstract 1
- BCESCHGDVIYYPC-UHFFFAOYSA-N 2-(ethylamino)phenol Chemical compound CCNC1=CC=CC=C1O BCESCHGDVIYYPC-UHFFFAOYSA-N 0.000 abstract 1
- ZJUKNVKYUDCDIR-UHFFFAOYSA-K 2-carboxyquinolin-8-olate cerium(3+) Chemical compound [Ce+3].Oc1cccc2ccc(nc12)C([O-])=O.Oc1cccc2ccc(nc12)C([O-])=O.Oc1cccc2ccc(nc12)C([O-])=O ZJUKNVKYUDCDIR-UHFFFAOYSA-K 0.000 abstract 1
- ZHDRUIVPJYQJEK-UHFFFAOYSA-N 2-cyclohexyloxybenzaldehyde Chemical compound O=CC1=CC=CC=C1OC1CCCCC1 ZHDRUIVPJYQJEK-UHFFFAOYSA-N 0.000 abstract 1
- NTCCNERMXRIPTR-UHFFFAOYSA-N 2-hydroxy-1-naphthaldehyde Chemical compound C1=CC=CC2=C(C=O)C(O)=CC=C21 NTCCNERMXRIPTR-UHFFFAOYSA-N 0.000 abstract 1
- ILEIUTCVWLYZOM-UHFFFAOYSA-N 2-hydroxy-5-methylbenzaldehyde Chemical compound CC1=CC=C(O)C(C=O)=C1 ILEIUTCVWLYZOM-UHFFFAOYSA-N 0.000 abstract 1
- GUARKOVVHJSMRW-UHFFFAOYSA-N 3-ethylpentane-2,4-dione Chemical compound CCC(C(C)=O)C(C)=O GUARKOVVHJSMRW-UHFFFAOYSA-N 0.000 abstract 1
- QCUNDLUTTXSPFM-UHFFFAOYSA-N 3-hydroxynaphthalene-2-carbaldehyde Chemical compound C1=CC=C2C=C(C=O)C(O)=CC2=C1 QCUNDLUTTXSPFM-UHFFFAOYSA-N 0.000 abstract 1
- KJBBCALDDPYKRJ-UHFFFAOYSA-N 3-methylidenetridec-1-ene Chemical compound CCCCCCCCCCC(=C)C=C KJBBCALDDPYKRJ-UHFFFAOYSA-N 0.000 abstract 1
- OYUKRQOCPFZNHR-UHFFFAOYSA-N 4-methylquinolin-8-ol Chemical compound C1=CC=C2C(C)=CC=NC2=C1O OYUKRQOCPFZNHR-UHFFFAOYSA-N 0.000 abstract 1
- BUXCYBWPYNCJGR-UHFFFAOYSA-N 5-cyclohexyl-2-hydroxybenzaldehyde Chemical compound C1=C(C=O)C(O)=CC=C1C1CCCCC1 BUXCYBWPYNCJGR-UHFFFAOYSA-N 0.000 abstract 1
- 239000005725 8-Hydroxyquinoline Substances 0.000 abstract 1
- UHBIKXOBLZWFKM-UHFFFAOYSA-N 8-hydroxy-2-quinolinecarboxylic acid Chemical compound C1=CC=C(O)C2=NC(C(=O)O)=CC=C21 UHBIKXOBLZWFKM-UHFFFAOYSA-N 0.000 abstract 1
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 abstract 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 abstract 1
- VKHJQPXNHWJVIZ-UHFFFAOYSA-N CC(C)(C)OC1=CC=CC=C1C=O.Cl Chemical compound CC(C)(C)OC1=CC=CC=C1C=O.Cl VKHJQPXNHWJVIZ-UHFFFAOYSA-N 0.000 abstract 1
- WWZKQHOCKIZLMA-UHFFFAOYSA-N Caprylic acid Natural products CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 abstract 1
- 229910004755 Cerium(III) bromide Inorganic materials 0.000 abstract 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 abstract 1
- 239000005977 Ethylene Substances 0.000 abstract 1
- 239000005639 Lauric acid Substances 0.000 abstract 1
- RWNNIPGWFQUQIN-UHFFFAOYSA-K OC=1C=CC=C2C=CC(=NC12)C(=O)[O-].OC=1C=CC=C2C=CC(=NC12)C(=O)[O-].OC=1C=CC=C2C=CC(=NC12)C(=O)[O-].[La+3] Chemical compound OC=1C=CC=C2C=CC(=NC12)C(=O)[O-].OC=1C=CC=C2C=CC(=NC12)C(=O)[O-].OC=1C=CC=C2C=CC(=NC12)C(=O)[O-].[La+3] RWNNIPGWFQUQIN-UHFFFAOYSA-K 0.000 abstract 1
- 235000021355 Stearic acid Nutrition 0.000 abstract 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 abstract 1
- 239000007983 Tris buffer Substances 0.000 abstract 1
- ILRSVJNIPQRFSN-UHFFFAOYSA-L [Cl-].[Cl-].C(C=1C(O)=CC=CC1)=O.[Ce+2] Chemical compound [Cl-].[Cl-].C(C=1C(O)=CC=CC1)=O.[Ce+2] ILRSVJNIPQRFSN-UHFFFAOYSA-L 0.000 abstract 1
- 125000005234 alkyl aluminium group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 abstract 1
- GONOPSZTUGRENK-UHFFFAOYSA-N benzyl(trichloro)silane Chemical compound Cl[Si](Cl)(Cl)CC1=CC=CC=C1 GONOPSZTUGRENK-UHFFFAOYSA-N 0.000 abstract 1
- HQMRIBYCTLBDAK-UHFFFAOYSA-M bis(2-methylpropyl)alumanylium;chloride Chemical compound CC(C)C[Al](Cl)CC(C)C HQMRIBYCTLBDAK-UHFFFAOYSA-M 0.000 abstract 1
- 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 abstract 1
- MOOUSOJAOQPDEH-UHFFFAOYSA-K cerium(iii) bromide Chemical compound [Br-].[Br-].[Br-].[Ce+3] MOOUSOJAOQPDEH-UHFFFAOYSA-K 0.000 abstract 1
- 239000007795 chemical reaction product Substances 0.000 abstract 1
- SPQJTJAPBKMHMO-UHFFFAOYSA-K dysprosium(3+);2-ethylhexanoate Chemical compound [Dy+3].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O SPQJTJAPBKMHMO-UHFFFAOYSA-K 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 1
- BMOAQMNPJSPXIU-UHFFFAOYSA-N ethyl 2-(3-fluoro-4-nitrophenyl)propanoate Chemical compound CCOC(=O)C(C)C1=CC=C([N+]([O-])=O)C(F)=C1 BMOAQMNPJSPXIU-UHFFFAOYSA-N 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- LHGVFZTZFXWLCP-UHFFFAOYSA-N guaiacol Chemical compound COC1=CC=CC=C1O LHGVFZTZFXWLCP-UHFFFAOYSA-N 0.000 abstract 1
- 150000004820 halides Chemical class 0.000 abstract 1
- NDOGLIPWGGRQCO-UHFFFAOYSA-N hexane-2,4-dione Chemical compound CCC(=O)CC(C)=O NDOGLIPWGGRQCO-UHFFFAOYSA-N 0.000 abstract 1
- 150000004678 hydrides Chemical class 0.000 abstract 1
- 239000003446 ligand Substances 0.000 abstract 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 abstract 1
- 150000002739 metals Chemical class 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N n-hexanoic acid Natural products CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 abstract 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 abstract 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 abstract 1
- GJYXGIIWJFZCLN-UHFFFAOYSA-N octane-2,4-dione Chemical compound CCCCC(=O)CC(C)=O GJYXGIIWJFZCLN-UHFFFAOYSA-N 0.000 abstract 1
- 150000002894 organic compounds Chemical class 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 229960003540 oxyquinoline Drugs 0.000 abstract 1
- 235000019260 propionic acid Nutrition 0.000 abstract 1
- KRIOVPPHQSLHCZ-UHFFFAOYSA-N propiophenone Chemical compound CCC(=O)C1=CC=CC=C1 KRIOVPPHQSLHCZ-UHFFFAOYSA-N 0.000 abstract 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 abstract 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 abstract 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 abstract 1
- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical compound C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 abstract 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 239000008117 stearic acid Substances 0.000 abstract 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 abstract 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 abstract 1
- 229940005605 valeric acid Drugs 0.000 abstract 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/22—Organic complexes
- B01J31/2204—Organic complexes the ligands containing oxygen or sulfur as complexing atoms
- B01J31/2208—Oxygen, e.g. acetylacetonates
- B01J31/2226—Anionic ligands, i.e. the overall ligand carries at least one formal negative charge
- B01J31/2243—At least one oxygen and one nitrogen atom present as complexing atoms in an at least bidentate or bridging ligand
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/12—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides
- B01J31/14—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides of aluminium or boron
- B01J31/143—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides of aluminium or boron of aluminium
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/22—Organic complexes
- B01J31/2204—Organic complexes the ligands containing oxygen or sulfur as complexing atoms
- B01J31/2208—Oxygen, e.g. acetylacetonates
- B01J31/2226—Anionic ligands, i.e. the overall ligand carries at least one formal negative charge
- B01J31/223—At least two oxygen atoms present in one at least bidentate or bridging ligand
-
- 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
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/30—Complexes comprising metals of Group III (IIIA or IIIB) as the central metal
- B01J2531/37—Lanthanum
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/30—Complexes comprising metals of Group III (IIIA or IIIB) as the central metal
- B01J2531/38—Lanthanides other than lanthanum
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Inorganic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US261875A US3297667A (en) | 1963-02-28 | 1963-02-28 | Production of cis-1, 4-polydienes by polymerization of 1, 3-dienes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1061002A true GB1061002A (en) | 1967-03-08 |
Family
ID=22995253
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB5595/64A Expired GB1061002A (en) | 1963-02-28 | 1964-02-11 | Polymerization catalyst and use thereof |
Country Status (6)
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2399447A1 (fr) * | 1977-08-01 | 1979-03-02 | Anic Spa | Procede pour la polymerisation et la copolymerisation de diolefine et moyens utilises pour ce procede |
| DE2848964A1 (de) * | 1978-11-11 | 1980-05-22 | Bayer Ag | Katalysator, dessen herstellung und verwendung zur loesungspolymerisation von butadien |
Families Citing this family (71)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1030932A (en) * | 1963-10-30 | 1966-05-25 | Mitsui Chemical Ind Co Ltd | Method for polymerizing conjugated diolefines |
| IT1151542B (it) * | 1982-04-15 | 1986-12-24 | Anic Spa | Procedimento per la polimerizzazione di diolefine coniugate e mezzi adatti allo scopo |
| US4556647A (en) * | 1984-09-13 | 1985-12-03 | Phillips Petroleum Company | Olefin polymerization |
| US4544718A (en) * | 1984-09-13 | 1985-10-01 | Phillips Petroleum Company | Olefin polymerization |
| US4575538A (en) * | 1984-12-20 | 1986-03-11 | Phillips Petroleum Company | Olefin polymerization |
| DE4334045A1 (de) * | 1993-10-06 | 1995-04-13 | Bayer Ag | Katalysator, dessen Herstellung und Verwendung zur Gasphasenpolymerisation von konjugierten Dienen |
| DE19512116A1 (de) * | 1995-04-04 | 1996-10-10 | Bayer Ag | Gasphasenpolymerisation von konjugierten Dienen in Gegenwart von Allylverbindungen der seltenen Erden |
| US6001478A (en) * | 1997-08-08 | 1999-12-14 | Union Carbide Chemicals & Plastics Technology Corporation | Resin particle produced by diene polymerization with rare earth and transition metal catalysts |
| DE19806931A1 (de) * | 1998-02-19 | 1999-08-26 | Bayer Ag | Verfahren zur Herstellung von Polydienen mit geregelter Mooney-Viskosität |
| WO2000059955A1 (fr) * | 1999-04-06 | 2000-10-12 | Mitsui Chemicals, Incorporated | Catalyseur de polymerisation, nouveau compose de metaux de transition, procede de polymerisation et copolymere dans lequel ils sont utilises |
| US6992147B1 (en) * | 1999-11-12 | 2006-01-31 | Bridgestone Corporation | Modified polymers prepared with lanthanide-based catalysts |
| US6977281B1 (en) * | 1999-11-12 | 2005-12-20 | Bridgestone Corporation | Modified polymers prepared with lanthanide-based catalysts |
| ES2412979T3 (es) | 2000-11-10 | 2013-07-15 | Bridgestone Corporation | Cis-1,4-polibutadieno altamente funcionalizado preparado usando nuevos agentes de funcionalización |
| DE10135314A1 (de) * | 2001-07-19 | 2003-01-30 | Bayer Ag | Aufarbeitung von Polymersyntheselösungen |
| US9226876B2 (en) * | 2001-10-19 | 2016-01-05 | The Goodyear Tire & Rubber Company | Rubber for baby bottle nipples, pacifiers, and syringe plungers |
| US6871751B2 (en) * | 2001-10-19 | 2005-03-29 | The Goodyear Tire & Rubber Company | Rubber for baby bottle nipples, pacifiers, & syringe plungers |
| US6699813B2 (en) | 2001-11-07 | 2004-03-02 | Bridgestone Corporation | Lanthanide-based catalyst composition for the manufacture of polydienes |
| US6780948B2 (en) | 2002-03-28 | 2004-08-24 | The Goodyear Tire & Rubber Company | Synthesis of polyisoprene with neodymium catalyst |
| US7008899B2 (en) * | 2003-08-11 | 2006-03-07 | Bridgestone Corporation | Lanthanide-based catalyst composition for producing cis-1,4-polydienes |
| US7094849B2 (en) * | 2003-12-15 | 2006-08-22 | Bridgestone Corporation | Bulk polymerization process for producing polydienes |
| US7091150B2 (en) * | 2003-12-19 | 2006-08-15 | The Goodyear Tire & Rubber Company | Synthetic polyisoprene rubber |
| JP5111101B2 (ja) | 2004-03-02 | 2012-12-26 | 株式会社ブリヂストン | バルク重合プロセス |
| DE102004022676A1 (de) * | 2004-05-07 | 2005-12-15 | Bayer Ag | Hydrierte Copolymerisate aus nicht substituierten und substituierten konjugierten Dienen |
| JP4294011B2 (ja) * | 2004-07-21 | 2009-07-08 | 日信工業株式会社 | 炭素系材料及びその製造方法、複合材料の製造方法 |
| JP4279220B2 (ja) * | 2004-09-09 | 2009-06-17 | 日信工業株式会社 | 複合材料及びその製造方法、複合金属材料及びその製造方法 |
| US7879952B2 (en) * | 2005-12-28 | 2011-02-01 | Bridgestone Corporation | Functionalized polymers |
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| US7795354B2 (en) | 2006-06-16 | 2010-09-14 | Georgia-Pacific Chemicals Llc | Formaldehyde free binder |
| US7732534B2 (en) * | 2006-08-28 | 2010-06-08 | Bridgestone Corporation | Polymers functionalized with nitro compounds |
| US8088868B2 (en) | 2006-12-19 | 2012-01-03 | Bridgestone Corporation | Polymers functionalized with protected oxime compounds |
| US7879958B2 (en) * | 2007-08-07 | 2011-02-01 | Bridgestone Corporation | Polyhydroxy compounds as polymerization quenching agents |
| US7825201B2 (en) * | 2007-12-31 | 2010-11-02 | Bridgestone Corporation | Process for producing polydienes |
| US8268933B2 (en) * | 2007-12-31 | 2012-09-18 | Bridgestone Corporation | Polymers functionalized with polyimine compounds |
| US7741418B2 (en) * | 2007-12-31 | 2010-06-22 | Bridgestone Corporation | Process for producing polydienes |
| RU2515980C2 (ru) * | 2007-12-31 | 2014-05-20 | Бриджстоун Корпорейшн | Способ получения полидиенов полимеризацией в объеме |
| US7807763B2 (en) | 2008-04-07 | 2010-10-05 | Bridgestone Corporation | Method for bulk polymerization |
| US7906592B2 (en) * | 2008-07-03 | 2011-03-15 | Bridgestone Corporation | Polymers functionalized with imide compounds containing a protected amino group |
| US8188195B2 (en) | 2008-12-31 | 2012-05-29 | Bridgestone Corporation | Polymers functionalized with nitroso compounds |
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| US8785566B2 (en) | 2009-01-23 | 2014-07-22 | Bridgestone Corporation | Polymers functionalized with polycyano compounds |
| US7902309B2 (en) | 2009-02-23 | 2011-03-08 | Bridgestone Corporation | Process and catalyst system for polydiene production |
| FR2944800B1 (fr) * | 2009-04-28 | 2012-10-26 | Michelin Soc Tech | Systemes catalytiques a base d'un complexe de terres rares pour la polymerisation stereospecifique des dienes conjugues |
| US8623975B2 (en) | 2009-06-24 | 2014-01-07 | Bridgestone Corporation | Process for producing polydienes |
| WO2011047021A1 (en) | 2009-10-14 | 2011-04-21 | Bridgestone Corporation | Processes for preparation of cyclic acyclic diene copolymer and rubber composition |
| US8338544B2 (en) * | 2009-12-21 | 2012-12-25 | Bridgestone Corporation | Polymers functionalized with polyoxime compounds and methods for their manufacture |
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| US8748531B2 (en) | 2010-12-10 | 2014-06-10 | Bridgestone Corporation | Polymers functionalized with oxime compounds containing an acyl group |
| US9000107B2 (en) | 2011-01-31 | 2015-04-07 | Bridgestone Corporation | Process for producing polydienes |
| US8962766B2 (en) | 2011-09-15 | 2015-02-24 | Bridgestone Corporation | Polymers functionalized with polyhydrazone compounds |
| CN104039843B (zh) | 2011-11-17 | 2016-05-18 | 株式会社普利司通 | 制备聚二烯的方法 |
| SG11201404817VA (en) | 2012-02-27 | 2014-09-26 | Bridgestone Corp | Processes for the preparation of high-cis polydienes |
| US8685513B1 (en) | 2012-02-29 | 2014-04-01 | Carolyn M. Dry | Inflatable articles comprising a self-repairing laminate |
| US9694629B1 (en) | 2012-02-29 | 2017-07-04 | Carolyn Dry | Self-repairing inflatable articles incorporating an integrated self-repair system |
| WO2013138270A1 (en) | 2012-03-14 | 2013-09-19 | Bridgestsone Corporation | Process for producing polydienes |
| JP6069044B2 (ja) * | 2013-03-12 | 2017-01-25 | 住友ゴム工業株式会社 | ベーストレッド用ゴム組成物及び空気入りタイヤ |
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| TWI522378B (zh) | 2013-12-13 | 2016-02-21 | 奇美實業股份有限公司 | 改質的高順式丁二烯-異戊二烯系共聚物、其製造方法及含有前述聚合物的輪胎 |
| TWI508979B (zh) | 2013-12-18 | 2015-11-21 | Chi Mei Corp | 改質的高順式異戊二烯聚合物、其製造方法及含有前述聚合物的輪胎 |
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| EP3237526B1 (en) | 2014-12-23 | 2022-05-18 | Bridgestone Americas Tire Operations, LLC | Tire comprising an oil-containing rubber composition |
| US10202474B2 (en) | 2015-09-11 | 2019-02-12 | Bridgestone Corporation | Process for producing polydienes |
| US10730985B2 (en) | 2016-12-19 | 2020-08-04 | Bridgestone Corporation | Functionalized polymer, process for preparing and rubber compositions containing the functionalized polymer |
| CN111630075B (zh) | 2017-12-15 | 2023-04-28 | 株式会社普利司通 | 官能化聚合物、用于制备该官能化聚合物的方法和含有该官能化聚合物的橡胶组合物 |
| EP3732210A4 (en) | 2017-12-30 | 2021-08-11 | Bridgestone Corporation | COMPOSITION INCLUDING MULTIPLE POLYMERS WITH TERMINAL FUNCTIONALIZATION |
| JP7238154B2 (ja) | 2019-03-10 | 2023-03-13 | 株式会社ブリヂストン | 変性高シスポリジエンポリマー、関連する方法及びゴム組成物 |
| US11767388B1 (en) | 2019-09-18 | 2023-09-26 | The Goodyear Tire & Rubber Company | Silicon-functionalized rubber |
| EP3838932B1 (en) | 2019-12-20 | 2022-08-10 | The Goodyear Tire & Rubber Company | Synthesis of isoprene-butadiene copolymer rubbers |
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Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3094514A (en) * | 1958-02-13 | 1963-06-18 | Goodrich Gulf Chem Inc | Polymerization process for aliphatic, conjugated dienes |
| IN57789B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1955-07-29 | |||
| GB865248A (en) * | 1956-12-28 | 1961-04-12 | Hoechst Ag | Process for the polymerisation of olefines |
| AT213051B (de) * | 1958-04-24 | 1961-01-25 | Montedison Spa | Verfahren zum Polymerisieren von Diolefinen mit wenigstens einer Vinyldoppelbindung |
| NL257561A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1959-11-18 | |||
| FR1281516A (fr) * | 1959-12-31 | 1962-01-12 | Bridgestone Tire Co Ltd | Procédé de préparation de cis-1, 4 polybutadiène et catalyseur pour sa mise en oeuvre et produits obtenus |
-
1963
- 1963-02-28 US US261875A patent/US3297667A/en not_active Expired - Lifetime
-
1964
- 1964-02-11 GB GB5595/64A patent/GB1061002A/en not_active Expired
- 1964-02-25 BE BE644291D patent/BE644291A/xx unknown
- 1964-02-26 FR FR965269A patent/FR1390509A/fr not_active Expired
- 1964-02-26 DE DE19641542529 patent/DE1542529A1/de active Pending
- 1964-02-26 DE DE19641302264D patent/DE1302264B/de active Pending
- 1964-02-28 NL NL6401996A patent/NL6401996A/xx unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2399447A1 (fr) * | 1977-08-01 | 1979-03-02 | Anic Spa | Procede pour la polymerisation et la copolymerisation de diolefine et moyens utilises pour ce procede |
| DE2848964A1 (de) * | 1978-11-11 | 1980-05-22 | Bayer Ag | Katalysator, dessen herstellung und verwendung zur loesungspolymerisation von butadien |
Also Published As
| Publication number | Publication date |
|---|---|
| NL6401996A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1964-08-31 |
| DE1542529A1 (de) | 1970-07-23 |
| US3297667A (en) | 1967-01-10 |
| DE1302264B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1970-11-12 |
| BE644291A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1964-06-15 |
| FR1390509A (fr) | 1965-02-26 |
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