DE2704763C2 - - Google Patents
Info
- Publication number
- DE2704763C2 DE2704763C2 DE19772704763 DE2704763A DE2704763C2 DE 2704763 C2 DE2704763 C2 DE 2704763C2 DE 19772704763 DE19772704763 DE 19772704763 DE 2704763 A DE2704763 A DE 2704763A DE 2704763 C2 DE2704763 C2 DE 2704763C2
- Authority
- DE
- Germany
- Prior art keywords
- catalyst
- alcoholate
- barium
- polymerization
- lithium
- 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
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 claims description 31
- 238000000034 method Methods 0.000 claims description 23
- 239000003054 catalyst Substances 0.000 claims description 22
- 238000006116 polymerization reaction Methods 0.000 claims description 22
- 239000000203 mixture Substances 0.000 claims description 16
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 15
- 229910052788 barium Inorganic materials 0.000 claims description 11
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 claims description 11
- -1 alkaline earth metal alkoxide Chemical class 0.000 claims description 10
- 229910052744 lithium Inorganic materials 0.000 claims description 6
- VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 claims description 6
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical group [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 5
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 claims description 4
- 229910052782 aluminium Inorganic materials 0.000 claims description 4
- 239000011575 calcium Substances 0.000 claims description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- 150000002900 organolithium compounds Chemical class 0.000 claims description 4
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- 150000001340 alkali metals Chemical class 0.000 claims description 3
- 229910052791 calcium Inorganic materials 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- HQWPLXHWEZZGKY-UHFFFAOYSA-N diethylzinc Chemical compound CC[Zn]CC HQWPLXHWEZZGKY-UHFFFAOYSA-N 0.000 claims description 3
- 229920002554 vinyl polymer Polymers 0.000 claims description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 2
- 150000002902 organometallic compounds Chemical class 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 229910052712 strontium Inorganic materials 0.000 claims description 2
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 claims description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 claims 2
- 229940031826 phenolate Drugs 0.000 claims 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group 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 claims 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical group [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 1
- 125000001931 aliphatic group Chemical group 0.000 claims 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims 1
- HMOHOVASWYMMHA-UHFFFAOYSA-L barium(2+);diphenoxide Chemical compound [Ba+2].[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1 HMOHOVASWYMMHA-UHFFFAOYSA-L 0.000 claims 1
- 229910052751 metal Inorganic materials 0.000 claims 1
- 239000002184 metal Substances 0.000 claims 1
- 230000000737 periodic effect Effects 0.000 claims 1
- 229910052700 potassium Chemical group 0.000 claims 1
- 239000011591 potassium Chemical group 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- 239000011734 sodium Chemical group 0.000 claims 1
- MCULRUJILOGHCJ-UHFFFAOYSA-N triisobutylaluminium Chemical compound CC(C)C[Al](CC(C)C)CC(C)C MCULRUJILOGHCJ-UHFFFAOYSA-N 0.000 claims 1
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 40
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 32
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 24
- 229920000642 polymer Polymers 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 229910052757 nitrogen Inorganic materials 0.000 description 12
- SBMJKCDBJMFHGS-UHFFFAOYSA-L barium(2+);2-nonylphenolate Chemical compound [Ba+2].CCCCCCCCCC1=CC=CC=C1[O-].CCCCCCCCCC1=CC=CC=C1[O-] SBMJKCDBJMFHGS-UHFFFAOYSA-L 0.000 description 10
- 229920001577 copolymer Polymers 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000000178 monomer Substances 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 244000043261 Hevea brasiliensis Species 0.000 description 5
- 229920003052 natural elastomer Polymers 0.000 description 5
- 229920001194 natural rubber Polymers 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000003513 alkali Substances 0.000 description 4
- 238000007334 copolymerization reaction Methods 0.000 description 4
- 229920001971 elastomer Polymers 0.000 description 4
- 229920002857 polybutadiene Polymers 0.000 description 4
- 239000000806 elastomer Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- 239000005062 Polybutadiene Substances 0.000 description 2
- 229910052796 boron Inorganic materials 0.000 description 2
- 229910052793 cadmium Inorganic materials 0.000 description 2
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 description 2
- 229940043430 calcium compound Drugs 0.000 description 2
- 150000001674 calcium compounds Chemical class 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 230000001105 regulatory effect Effects 0.000 description 2
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 description 1
- OLUHBJVZBNXWIX-UHFFFAOYSA-M C(COCC(=O)[O-])(=O)OCC.[Li+] Chemical compound C(COCC(=O)[O-])(=O)OCC.[Li+] OLUHBJVZBNXWIX-UHFFFAOYSA-M 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 239000011952 anionic catalyst Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 1
- VQNPSCRXHSIJTH-UHFFFAOYSA-N cadmium(2+);carbanide Chemical compound [CH3-].[CH3-].[Cd+2] VQNPSCRXHSIJTH-UHFFFAOYSA-N 0.000 description 1
- JHLCADGWXYCDQA-UHFFFAOYSA-N calcium;ethanolate Chemical compound [Ca+2].CC[O-].CC[O-] JHLCADGWXYCDQA-UHFFFAOYSA-N 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- UHZZMRAGKVHANO-UHFFFAOYSA-M chlormequat chloride Chemical compound [Cl-].C[N+](C)(C)CCCl UHZZMRAGKVHANO-UHFFFAOYSA-M 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000011874 heated mixture Substances 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 150000002642 lithium compounds Chemical class 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 238000007493 shaping process Methods 0.000 description 1
- 150000003438 strontium compounds Chemical class 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- LALRXNPLTWZJIJ-UHFFFAOYSA-N triethylborane Chemical compound CCB(CC)CC LALRXNPLTWZJIJ-UHFFFAOYSA-N 0.000 description 1
- LFXVBWRMVZPLFK-UHFFFAOYSA-N trioctylalumane Chemical compound CCCCCCCC[Al](CCCCCCCC)CCCCCCCC LFXVBWRMVZPLFK-UHFFFAOYSA-N 0.000 description 1
- 150000003682 vanadium compounds Chemical class 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- 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)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Polymerization Catalysts (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7419475A FR2273822A1 (fr) | 1974-06-05 | 1974-06-05 | Polymeres ou copolymeres a composition sterique modifiee, obtenus par mise en oeuvre d'une nouvelle composition catalytique |
| FR7604115A FR2340958A2 (fr) | 1974-06-05 | 1976-02-12 | Procede de polymerisation ou de copolymerisation de dienes conjugues et polymeres ainsi obtenus |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2704763A1 DE2704763A1 (de) | 1977-08-18 |
| DE2704763C2 true DE2704763C2 (enrdf_load_stackoverflow) | 1987-10-22 |
Family
ID=26218363
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19772704763 Granted DE2704763A1 (de) | 1974-06-05 | 1977-02-04 | Verfahren zur herstellung von elastomeren butadienpolymerisaten oder -copolymerisaten |
Country Status (7)
| Country | Link |
|---|---|
| AT (1) | AT351758B (enrdf_load_stackoverflow) |
| BE (1) | BE882565Q (enrdf_load_stackoverflow) |
| DE (1) | DE2704763A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2340958A2 (enrdf_load_stackoverflow) |
| GB (1) | GB1525381A (enrdf_load_stackoverflow) |
| LU (1) | LU76740A1 (enrdf_load_stackoverflow) |
| NL (1) | NL167977C (enrdf_load_stackoverflow) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5527337A (en) | 1978-08-18 | 1980-02-27 | Asahi Chem Ind Co Ltd | Isoprene-butadiene copolymer rubber having improved processability |
| US4297240A (en) | 1980-02-25 | 1981-10-27 | The General Tire & Rubber Company | Solution polymerization |
| US4302568A (en) * | 1980-02-25 | 1981-11-24 | The General Tire & Rubber Co. | Solution polymerization |
| FR2480288A1 (fr) * | 1980-04-09 | 1981-10-16 | Michelin & Cie | Procede de preparation de polymeres de dienes conjugues ou de copolymeres conjugues soit entre eux, soit avec un compose vinylaromatique |
| FR2480291A1 (fr) * | 1980-04-09 | 1981-10-16 | Michelin & Cie | Procede de preparation de polymeres de dienes conjugues ou de copolymeres de dienes conjugues soit entre eux, soit avec un compose vinylaromatique |
| JPS57159807A (en) * | 1981-03-27 | 1982-10-02 | Asahi Chem Ind Co Ltd | Production of conjugated diene polymer |
| FR2567135B1 (fr) * | 1984-07-03 | 1989-01-13 | Asahi Chemical Ind | Polymere ou copolymere de butadiene et procede de preparation |
| US4933401A (en) * | 1988-02-26 | 1990-06-12 | Japan Synthetic Rubber Co., Ltd. | Catalyst composition for polymerization of conjugated diene and process for producing conjugated diene polymer |
| US5100965A (en) * | 1991-04-08 | 1992-03-31 | The Goodyear Tire & Rubber Company | Process for synthesizing high trans polymers |
| FR2722503A1 (fr) | 1994-07-15 | 1996-01-19 | Michelin & Cie | Polymeres dieniques fonctionnels, leur procede de preparation et leur utilisation dans des compositions elastomeres chargees a la silice utilisables pour des enveloppes de pneumatiques |
| FR2722505B1 (fr) | 1994-07-15 | 1996-09-27 | Michelin & Cie | Compositions elastomeres chargees a la silice utilisables pour des enveloppes de pneumatiques |
| FR2744127A1 (fr) | 1996-01-26 | 1997-08-01 | Michelin & Cie | Composition de caoutchouc a base d'un polymere dienique ayant une fonction silanol et comprenant un derive organosilane |
| DE19646066A1 (de) * | 1996-11-08 | 1998-05-14 | Basf Ag | Initiatorsysteme für die anionische Polymerisation von Vinylmonomeren mit polaren Gruppen |
| US6018007A (en) * | 1997-09-22 | 2000-01-25 | Bridgestone Corporation | Synthesis of 1,4-trans-polybutadiene using a lanthanide organic acid salt catalyst |
| EP1448647A2 (fr) | 2001-10-31 | 2004-08-25 | Société de Technologie Michelin | Procede de preparation de copolymeres a blocs pour compositions de bande de roulement de pneumatique |
| FR2854636B1 (fr) | 2003-05-07 | 2006-07-14 | Michelin Soc Tech | Procede de preparation de copolymeres a blocs pour compositions de bande de roulement de pneumatique, et ces copolymeres |
| FR2854635B1 (fr) | 2003-05-07 | 2006-07-14 | Michelin Soc Tech | Procede de preparation de copolymeres a blocs pour compositions de bande de roulement de pneumatique, et ces copolymeres |
| FR2951186B1 (fr) | 2009-10-12 | 2012-01-06 | Michelin Soc Tech | Composition de caoutchouc a base de glycerol et d'un elastomere fonctionnalise et bande de roulement pour pneumatique |
| FR2992649B1 (fr) | 2012-07-02 | 2015-06-19 | Michelin & Cie | Procede de synthese en continu d'un elastomere dienique |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL295376A (enrdf_load_stackoverflow) * | 1962-12-19 | |||
| FR2273822A1 (fr) * | 1974-06-05 | 1976-01-02 | Michelin & Cie | Polymeres ou copolymeres a composition sterique modifiee, obtenus par mise en oeuvre d'une nouvelle composition catalytique |
-
1976
- 1976-02-12 FR FR7604115A patent/FR2340958A2/fr active Granted
-
1977
- 1977-02-04 DE DE19772704763 patent/DE2704763A1/de active Granted
- 1977-02-10 AT AT89377A patent/AT351758B/de not_active IP Right Cessation
- 1977-02-10 LU LU76740A patent/LU76740A1/xx unknown
- 1977-02-11 NL NL7701476A patent/NL167977C/xx not_active IP Right Cessation
- 1977-02-11 GB GB579477A patent/GB1525381A/en not_active Expired
-
1980
- 1980-04-01 BE BE0/200062A patent/BE882565Q/fr not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| NL7701476A (nl) | 1977-08-16 |
| BE882565Q (fr) | 1980-07-31 |
| AT351758B (de) | 1979-08-10 |
| LU76740A1 (enrdf_load_stackoverflow) | 1977-08-19 |
| DE2704763A1 (de) | 1977-08-18 |
| NL167977C (nl) | 1982-02-16 |
| NL167977B (nl) | 1981-09-16 |
| ATA89377A (de) | 1979-01-15 |
| GB1525381A (en) | 1978-09-20 |
| FR2340958B2 (enrdf_load_stackoverflow) | 1979-07-20 |
| FR2340958A2 (fr) | 1977-09-09 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8162 | Independent application | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition |