JPH0220643B2 - - Google Patents
Info
- Publication number
- JPH0220643B2 JPH0220643B2 JP55053945A JP5394580A JPH0220643B2 JP H0220643 B2 JPH0220643 B2 JP H0220643B2 JP 55053945 A JP55053945 A JP 55053945A JP 5394580 A JP5394580 A JP 5394580A JP H0220643 B2 JPH0220643 B2 JP H0220643B2
- Authority
- JP
- Japan
- Prior art keywords
- polymerization
- styrene
- vinyl content
- butadiene copolymer
- properties
- 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 - Lifetime
Links
- 238000006116 polymerization reaction Methods 0.000 claims description 56
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 28
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 28
- 229920002554 vinyl polymer Polymers 0.000 claims description 28
- 229920003048 styrene butadiene rubber Polymers 0.000 claims description 21
- 239000002904 solvent Substances 0.000 claims description 15
- 239000002879 Lewis base Substances 0.000 claims description 14
- 150000007527 lewis bases Chemical class 0.000 claims description 14
- 238000009826 distribution Methods 0.000 claims description 13
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 11
- 229930195733 hydrocarbon Natural products 0.000 claims description 11
- 239000003999 initiator Substances 0.000 claims description 11
- 238000004519 manufacturing process Methods 0.000 claims description 10
- 125000001979 organolithium group Chemical group 0.000 claims description 10
- 239000004215 Carbon black (E152) Substances 0.000 claims description 9
- -1 alicyclic hydrocarbon Chemical class 0.000 claims description 8
- 150000002430 hydrocarbons Chemical class 0.000 claims description 8
- 239000003945 anionic surfactant Substances 0.000 claims description 5
- 230000000977 initiatory effect Effects 0.000 claims description 4
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 3
- 238000007334 copolymerization reaction Methods 0.000 claims description 3
- 229910052700 potassium Inorganic materials 0.000 claims description 2
- 229910052701 rubidium Inorganic materials 0.000 claims description 2
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- 230000000052 comparative effect Effects 0.000 description 15
- 229920000642 polymer Polymers 0.000 description 14
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 10
- 238000005096 rolling process Methods 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 229920001971 elastomer Polymers 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- 239000005060 rubber Substances 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 229920001577 copolymer Polymers 0.000 description 6
- 230000009477 glass transition Effects 0.000 description 4
- 239000000178 monomer Substances 0.000 description 4
- 229920002857 polybutadiene Polymers 0.000 description 4
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 3
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical group [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 3
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 3
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 3
- 239000003505 polymerization initiator Substances 0.000 description 3
- RRQYJINTUHWNHW-UHFFFAOYSA-N 1-ethoxy-2-(2-ethoxyethoxy)ethane Chemical compound CCOCCOCCOCC RRQYJINTUHWNHW-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- 229940019778 diethylene glycol diethyl ether Drugs 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 239000000446 fuel Substances 0.000 description 2
- 230000020169 heat generation Effects 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- GDOPTJXRTPNYNR-UHFFFAOYSA-N methylcyclopentane Chemical compound CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 description 2
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 2
- 150000003871 sulfonates Chemical class 0.000 description 2
- 238000004073 vulcanization Methods 0.000 description 2
- IEOPZUMPHCZMCS-ZCFIWIBFSA-N (2r)-2-(methoxymethyl)oxolane Chemical compound COC[C@H]1CCCO1 IEOPZUMPHCZMCS-ZCFIWIBFSA-N 0.000 description 1
- LZDKZFUFMNSQCJ-UHFFFAOYSA-N 1,2-diethoxyethane Chemical compound CCOCCOCC LZDKZFUFMNSQCJ-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- KIAMPLQEZAMORJ-UHFFFAOYSA-N 1-ethoxy-2-[2-(2-ethoxyethoxy)ethoxy]ethane Chemical compound CCOCCOCCOCCOCC KIAMPLQEZAMORJ-UHFFFAOYSA-N 0.000 description 1
- NAMDIHYPBYVYAP-UHFFFAOYSA-N 1-methoxy-2-(2-methoxyethoxy)ethane Chemical compound COCCOCCOC.COCCOCCOC NAMDIHYPBYVYAP-UHFFFAOYSA-N 0.000 description 1
- FRBJEDLSFZZCFY-UHFFFAOYSA-N 2,5-bis(methoxymethyl)oxolane Chemical compound COCC1CCC(COC)O1 FRBJEDLSFZZCFY-UHFFFAOYSA-N 0.000 description 1
- OKAMTPRCXVGTND-UHFFFAOYSA-N 2-methoxyoxolane Chemical compound COC1CCCO1 OKAMTPRCXVGTND-UHFFFAOYSA-N 0.000 description 1
- CRWNQZTZTZWPOF-UHFFFAOYSA-N 2-methyl-4-phenylpyridine Chemical compound C1=NC(C)=CC(C=2C=CC=CC=2)=C1 CRWNQZTZTZWPOF-UHFFFAOYSA-N 0.000 description 1
- HVCNXQOWACZAFN-UHFFFAOYSA-N 4-ethylmorpholine Chemical compound CCN1CCOCC1 HVCNXQOWACZAFN-UHFFFAOYSA-N 0.000 description 1
- SXRLRTAOSJEJCG-UHFFFAOYSA-N C=1C=CC=CC=1C(C=1C=CC=CC=1)([Li])CCC([Li])(C=1C=CC=CC=1)C1=CC=CC=C1 Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)([Li])CCC([Li])(C=1C=CC=CC=1)C1=CC=CC=C1 SXRLRTAOSJEJCG-UHFFFAOYSA-N 0.000 description 1
- ZSVBMZPGHCNSNF-UHFFFAOYSA-N CCC(C)CC([Li])C1=CC=CC(C([Li])CC(C)CC)=C1 Chemical compound CCC(C)CC([Li])C1=CC=CC(C([Li])CC(C)CC)=C1 ZSVBMZPGHCNSNF-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 241000357292 Monodactylus Species 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
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000005062 Polybutadiene Substances 0.000 description 1
- QWFRFVPEFDDMQD-UHFFFAOYSA-N [Li]CCCCCCCCCC[Li] Chemical compound [Li]CCCCCCCCCC[Li] QWFRFVPEFDDMQD-UHFFFAOYSA-N 0.000 description 1
- ICKXMDGNIZPYRS-UHFFFAOYSA-N [Li]CCCCCC[Li] Chemical compound [Li]CCCCCC[Li] ICKXMDGNIZPYRS-UHFFFAOYSA-N 0.000 description 1
- QQDSVXYDUMVTSQ-UHFFFAOYSA-N [Li]CCCCC[Li] Chemical compound [Li]CCCCC[Li] QQDSVXYDUMVTSQ-UHFFFAOYSA-N 0.000 description 1
- BZEZSORUWZUMNU-UHFFFAOYSA-N [Li]CCCC[Li] Chemical compound [Li]CCCC[Li] BZEZSORUWZUMNU-UHFFFAOYSA-N 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical group 0.000 description 1
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
- 230000003712 anti-aging effect Effects 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 229910052792 caesium Inorganic materials 0.000 description 1
- 238000011088 calibration curve Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 230000008094 contradictory effect Effects 0.000 description 1
- 230000002596 correlated effect Effects 0.000 description 1
- WJTCGQSWYFHTAC-UHFFFAOYSA-N cyclooctane Chemical compound C1CCCCCCC1 WJTCGQSWYFHTAC-UHFFFAOYSA-N 0.000 description 1
- 239000004914 cyclooctane Substances 0.000 description 1
- 238000000113 differential scanning calorimetry Methods 0.000 description 1
- BLHLJVCOVBYQQS-UHFFFAOYSA-N ethyllithium Chemical compound [Li]CC BLHLJVCOVBYQQS-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 1
- WGOPGODQLGJZGL-UHFFFAOYSA-N lithium;butane Chemical compound [Li+].CC[CH-]C WGOPGODQLGJZGL-UHFFFAOYSA-N 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 238000006864 oxidative decomposition reaction Methods 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 1
- PGOLTJPQCISRTO-UHFFFAOYSA-N vinyllithium Chemical compound [Li]C=C PGOLTJPQCISRTO-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 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
- 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
- C08F236/10—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 with vinyl-aromatic monomers
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)
- Polymerisation Methods In General (AREA)
- Tires In General (AREA)
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5394580A JPS56149413A (en) | 1980-04-22 | 1980-04-22 | Production of styrene/butadiene copolymer |
| US06/254,517 US4367325A (en) | 1980-04-22 | 1981-04-15 | Styrene-butadiene random copolymer and process for the production thereof |
| DE3115878A DE3115878C2 (de) | 1980-04-22 | 1981-04-21 | Aus Butadien- und Styroleinheiten aufgebautes Copolymerisat mit statistischer Verteilung der Monomereinheiten |
| GB8112427A GB2075524B (en) | 1980-04-22 | 1981-04-22 | Styrene-butadiene random copolymer and a process for its production |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5394580A JPS56149413A (en) | 1980-04-22 | 1980-04-22 | Production of styrene/butadiene copolymer |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS56149413A JPS56149413A (en) | 1981-11-19 |
| JPH0220643B2 true JPH0220643B2 (US20100056889A1-20100304-C00004.png) | 1990-05-10 |
Family
ID=12956856
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP5394580A Granted JPS56149413A (en) | 1980-04-22 | 1980-04-22 | Production of styrene/butadiene copolymer |
Country Status (4)
Families Citing this family (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5723613A (en) * | 1980-07-16 | 1982-02-06 | Sumitomo Chem Co Ltd | Preparation of conjugated diene polymer |
| JPS5753507A (en) * | 1980-09-17 | 1982-03-30 | Asahi Chem Ind Co Ltd | Butadiene polymer and its preparation |
| JPS5836705A (ja) * | 1981-08-27 | 1983-03-03 | Bridgestone Corp | 改良されたトレツドを有する空気入りタイヤ |
| GB8316052D0 (en) * | 1983-06-13 | 1983-07-20 | Shell Int Research | Elastomeric copolymers |
| GB8407629D0 (en) * | 1984-03-23 | 1984-05-02 | Shell Int Research | Preparation of polymers |
| US5164450A (en) * | 1984-05-16 | 1992-11-17 | Japan Synthetic Rubber Co. | Butadiene copolymer rubber composition |
| JPS61203145A (ja) * | 1985-03-05 | 1986-09-09 | Bridgestone Corp | 競技用タイヤ |
| JPS6236437A (ja) * | 1985-08-12 | 1987-02-17 | Bridgestone Corp | タイヤトレツド用ゴム組成物 |
| JPS6296545A (ja) * | 1985-10-23 | 1987-05-06 | Yokohama Rubber Co Ltd:The | タイヤトレツド用ゴム組成物 |
| US5231153A (en) * | 1992-04-06 | 1993-07-27 | The Goodyear Tire & Rubber Company | Anionic polymerization of conjugated dienes modified with alkyltetrahydrofurfuryl ethers |
| US5448003A (en) * | 1992-04-06 | 1995-09-05 | The Goodyear Tire & Rubber Company | Synthesis of rubbery polymer using anionic polymerization modifier |
| JP3485605B2 (ja) * | 1992-10-19 | 2004-01-13 | 株式会社ブリヂストン | 重合体の製造方法 |
| US5470929A (en) * | 1993-03-29 | 1995-11-28 | The Goodyear Tire & Rubber Company | Process for synthesizing styrene-isoprene rubber |
| US5359016A (en) * | 1993-03-29 | 1994-10-25 | The Goodyear Tire & Rubber Company | Process for the synthesis of styrene-isoprene rubber |
| US5536706A (en) * | 1994-09-02 | 1996-07-16 | Phillips Petroleum Company | Use of butadiene-styrene copolymers in crude oils |
| ES2233544T3 (es) | 2000-10-17 | 2005-06-16 | Societe De Technologie Michelin | Procedimiento de preparacion de un elastomero dienico por polimerizacion anionica. |
| US20040138371A1 (en) * | 2002-02-07 | 2004-07-15 | St. Clair David John | Gels from controlled distribution block copolymers |
| US20030181584A1 (en) * | 2002-02-07 | 2003-09-25 | Kraton Polymers U.S. Llc | Elastomeric articles prepared from controlled distribution block copolymers |
| US7141621B2 (en) * | 2002-02-07 | 2006-11-28 | Kraton Polymers U.S. Llc | Gels from controlled distribution block copolymers |
| US8222346B2 (en) | 2003-09-23 | 2012-07-17 | Dais-Analytic Corp. | Block copolymers and method for making same |
| CN100390213C (zh) * | 2005-01-31 | 2008-05-28 | 中国石化北京燕化石油化工股份有限公司 | 星型高乙烯基含量的溶聚共轭二烯烃/单乙烯基芳烃共聚物橡胶及其制备方法 |
| US20070066753A1 (en) * | 2005-09-16 | 2007-03-22 | Ehrlich Martin L | Highly processible compounds of high MW conventional block copolymers and controlled distribution block copolymers |
| ITMI20060385A1 (it) * | 2006-03-03 | 2007-09-04 | Polimeri Europa Spa | Procedimento in continuo per la preparazione di copolimeri randon dieni coniugati-vinil areni |
| CN101628959A (zh) | 2008-07-15 | 2010-01-20 | 中国石油化工集团公司 | 一种可发泡苯乙烯属单体-二烯烃共聚物、其制备方法和用途 |
| US9732178B1 (en) | 2008-07-24 | 2017-08-15 | Bridgestone Corporation | Block copolymers including high vinyl segments |
| KR101187270B1 (ko) | 2010-01-21 | 2012-10-04 | 주식회사 엘지화학 | 용액 중합 폴리스티렌-부타디엔 고무 및 이의 제조방법 |
| CN102234357B (zh) * | 2010-04-23 | 2013-06-19 | 中国石油化工集团公司 | 一种密封条用线型丁二烯苯乙烯共聚物材料及其制备和应用 |
| US10435545B2 (en) | 2012-04-26 | 2019-10-08 | The Goodyear Tire & Rubber Company | Triglyceride containing solution polymerization prepared styrene/butadiene elastomer and tire with component |
| US20130289183A1 (en) * | 2012-04-26 | 2013-10-31 | Michael Lester Kerns | Triglyceride containing solution polymerization prepared styrene/butadiene elastomer and tire with component |
| ITUB20150281A1 (it) * | 2015-03-13 | 2016-09-13 | Fastech S R L | Processo in soluzione per la produzione di copolimeri stirene-diene. |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4864181A (US20100056889A1-20100304-C00004.png) * | 1971-11-26 | 1973-09-05 | ||
| JPS491788A (US20100056889A1-20100304-C00004.png) * | 1972-03-30 | 1974-01-09 | ||
| JPS4945192A (US20100056889A1-20100304-C00004.png) * | 1972-09-06 | 1974-04-30 | ||
| JPS52101287A (en) * | 1976-02-20 | 1977-08-25 | Japan Synthetic Rubber Co Ltd | Preparation of conjugated diene polymers |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE637376A (US20100056889A1-20100304-C00004.png) * | 1958-05-23 | |||
| US3301840A (en) * | 1964-09-17 | 1967-01-31 | Phillips Petroleum Co | Preparation of polymers of conjugated dienes using organolithium/polar compound catalyst systems |
| US3366611A (en) * | 1965-01-06 | 1968-01-30 | Phillips Petroleum Co | Preparation of random copolymers |
| FR2053786A5 (US20100056889A1-20100304-C00004.png) * | 1969-07-17 | 1971-04-16 | Michelin & Cie | |
| US4022959A (en) * | 1969-11-22 | 1977-05-10 | Chemische Werke Huels Aktiengesellschaft | Organolithium-Lewis base polymerization of 1,3-butadiene and novel polybutadienes thus produced |
| JPS491788B1 (US20100056889A1-20100304-C00004.png) * | 1970-04-10 | 1974-01-16 | ||
| US3980625A (en) * | 1970-05-25 | 1976-09-14 | Asahi Kasei Kogyo Kabushiki Kaisha | Method for producing novel rubbery polymers from diene monomers |
| US3716495A (en) * | 1970-09-02 | 1973-02-13 | Phillips Petroleum Co | Polymerization initiator composition and use thereof |
| US4230841A (en) * | 1979-01-31 | 1980-10-28 | The Goodyear Tire & Rubber Company | Process for medium vinyl polybutadiene |
-
1980
- 1980-04-22 JP JP5394580A patent/JPS56149413A/ja active Granted
-
1981
- 1981-04-15 US US06/254,517 patent/US4367325A/en not_active Expired - Lifetime
- 1981-04-21 DE DE3115878A patent/DE3115878C2/de not_active Expired
- 1981-04-22 GB GB8112427A patent/GB2075524B/en not_active Expired
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4864181A (US20100056889A1-20100304-C00004.png) * | 1971-11-26 | 1973-09-05 | ||
| JPS491788A (US20100056889A1-20100304-C00004.png) * | 1972-03-30 | 1974-01-09 | ||
| JPS4945192A (US20100056889A1-20100304-C00004.png) * | 1972-09-06 | 1974-04-30 | ||
| JPS52101287A (en) * | 1976-02-20 | 1977-08-25 | Japan Synthetic Rubber Co Ltd | Preparation of conjugated diene polymers |
Also Published As
| Publication number | Publication date |
|---|---|
| DE3115878C2 (de) | 1985-09-19 |
| GB2075524B (en) | 1983-11-30 |
| DE3115878A1 (de) | 1982-01-14 |
| GB2075524A (en) | 1981-11-18 |
| US4367325A (en) | 1983-01-04 |
| JPS56149413A (en) | 1981-11-19 |
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