JPH0246062B2 - - Google Patents
Info
- Publication number
- JPH0246062B2 JPH0246062B2 JP57154585A JP15458582A JPH0246062B2 JP H0246062 B2 JPH0246062 B2 JP H0246062B2 JP 57154585 A JP57154585 A JP 57154585A JP 15458582 A JP15458582 A JP 15458582A JP H0246062 B2 JPH0246062 B2 JP H0246062B2
- Authority
- JP
- Japan
- Prior art keywords
- polybutadiene
- molecular weight
- polymer
- present
- rubber
- 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
- 229920002857 polybutadiene Polymers 0.000 claims description 39
- 239000005062 Polybutadiene Substances 0.000 claims description 31
- 239000000203 mixture Substances 0.000 claims description 16
- 238000005259 measurement Methods 0.000 claims description 4
- 238000000691 measurement method Methods 0.000 claims description 4
- 238000004458 analytical method Methods 0.000 claims description 3
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 claims description 2
- 229920000642 polymer Polymers 0.000 description 24
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 14
- 239000003054 catalyst Substances 0.000 description 12
- 238000000034 method Methods 0.000 description 12
- 229920001971 elastomer Polymers 0.000 description 11
- 238000006116 polymerization reaction Methods 0.000 description 11
- 239000005060 rubber Substances 0.000 description 11
- 229910052779 Neodymium Inorganic materials 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- 230000000052 comparative effect Effects 0.000 description 10
- QEFYFXOXNSNQGX-UHFFFAOYSA-N neodymium atom Chemical compound [Nd] QEFYFXOXNSNQGX-UHFFFAOYSA-N 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 8
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 6
- 238000005227 gel permeation chromatography Methods 0.000 description 6
- 230000000694 effects Effects 0.000 description 5
- -1 mononitrone Chemical compound 0.000 description 4
- 230000000704 physical effect Effects 0.000 description 4
- 238000004073 vulcanization Methods 0.000 description 4
- 244000043261 Hevea brasiliensis Species 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 229920003052 natural elastomer Polymers 0.000 description 3
- 229920001194 natural rubber Polymers 0.000 description 3
- 230000035882 stress Effects 0.000 description 3
- VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 description 3
- 239000002841 Lewis acid Substances 0.000 description 2
- 239000002879 Lewis base Substances 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- PBKONEOXTCPAFI-UHFFFAOYSA-N TCB Natural products ClC1=CC=C(Cl)C(Cl)=C1 PBKONEOXTCPAFI-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- 230000003712 anti-aging effect Effects 0.000 description 2
- 229920003244 diene elastomer Polymers 0.000 description 2
- YNLAOSYQHBDIKW-UHFFFAOYSA-M diethylaluminium chloride Chemical compound CC[Al](Cl)CC YNLAOSYQHBDIKW-UHFFFAOYSA-M 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 150000002430 hydrocarbons Chemical group 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 150000007517 lewis acids Chemical class 0.000 description 2
- 150000007527 lewis bases Chemical class 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 229920001195 polyisoprene Polymers 0.000 description 2
- 230000000379 polymerizing effect Effects 0.000 description 2
- 239000000523 sample Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- CVBUKMMMRLOKQR-UHFFFAOYSA-N 1-phenylbutane-1,3-dione Chemical compound CC(=O)CC(=O)C1=CC=CC=C1 CVBUKMMMRLOKQR-UHFFFAOYSA-N 0.000 description 1
- MHKLKWCYGIBEQF-UHFFFAOYSA-N 4-(1,3-benzothiazol-2-ylsulfanyl)morpholine Chemical compound C1COCCN1SC1=NC2=CC=CC=C2S1 MHKLKWCYGIBEQF-UHFFFAOYSA-N 0.000 description 1
- ICGLPKIVTVWCFT-UHFFFAOYSA-N 4-methylbenzenesulfonohydrazide Chemical compound CC1=CC=C(S(=O)(=O)NN)C=C1 ICGLPKIVTVWCFT-UHFFFAOYSA-N 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000005594 diketone group Chemical group 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 230000005251 gamma ray Effects 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- 150000002603 lanthanum Chemical class 0.000 description 1
- 150000002642 lithium compounds Chemical class 0.000 description 1
- FSQQTNAZHBEJLS-UPHRSURJSA-N maleamic acid Chemical compound NC(=O)\C=C/C(O)=O FSQQTNAZHBEJLS-UPHRSURJSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000002685 polymerization catalyst Substances 0.000 description 1
- 238000002203 pretreatment Methods 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- 229910052761 rare earth metal Inorganic materials 0.000 description 1
- 239000012744 reinforcing agent Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229920003051 synthetic elastomer Polymers 0.000 description 1
- 239000005061 synthetic rubber Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 235000014692 zinc oxide Nutrition 0.000 description 1
- 239000011787 zinc oxide 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
- C08F136/00—Homopolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds
- C08F136/02—Homopolymers 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
- C08F136/04—Homopolymers 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
- C08F136/06—Butadiene
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)
- Compositions Of Macromolecular Compounds (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57154585A JPS5945337A (ja) | 1982-09-07 | 1982-09-07 | 生強度の改良されたポリブタジエンゴム組成物 |
| CA000435667A CA1228697A (en) | 1982-09-07 | 1983-08-30 | Polybutadiene rubber compositions having improved green strength |
| US06/530,169 US4533711A (en) | 1982-09-07 | 1983-09-07 | Polybutadiene rubber compositions having improved green strength |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57154585A JPS5945337A (ja) | 1982-09-07 | 1982-09-07 | 生強度の改良されたポリブタジエンゴム組成物 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5945337A JPS5945337A (ja) | 1984-03-14 |
| JPH0246062B2 true JPH0246062B2 (en, 2012) | 1990-10-12 |
Family
ID=15587412
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP57154585A Granted JPS5945337A (ja) | 1982-09-07 | 1982-09-07 | 生強度の改良されたポリブタジエンゴム組成物 |
Country Status (3)
| Country | Link |
|---|---|
| US (1) | US4533711A (en, 2012) |
| JP (1) | JPS5945337A (en, 2012) |
| CA (1) | CA1228697A (en, 2012) |
Families Citing this family (37)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5945337B2 (ja) * | 1983-01-10 | 1984-11-06 | 株式会社 サンユ− | 生「あん」の製造法 |
| JPH0647636B2 (ja) * | 1985-04-23 | 1994-06-22 | 日本合成ゴム株式会社 | ジエン系ゴム組成物 |
| US4663405A (en) * | 1986-04-16 | 1987-05-05 | The Goodyear Tire & Rubber Company | Molecular weight modifier for use with lanthanide and actinide catalysts |
| JPH03190944A (ja) * | 1989-12-20 | 1991-08-20 | Nippon Zeon Co Ltd | 耐摩耗性ゴム組成物 |
| JPH048374A (ja) * | 1990-04-25 | 1992-01-13 | Sumitomo Rubber Ind Ltd | 無圧テニスボールの中空コア用ゴム組成物 |
| US5428119A (en) * | 1993-11-09 | 1995-06-27 | Polysar Rubber Corporation | Process for polybutadiene production using catalyst with high activity |
| DE4436059A1 (de) * | 1994-10-10 | 1996-04-11 | Bayer Ag | Verfahren zur Herstellung von mittels Nd-Katalysatoren polymerisierten Dienkautschuken mit niedrigem cold-flow und geringem Eigengeruch |
| KR100250231B1 (ko) * | 1998-03-03 | 2000-04-01 | 박찬구 | 고 1,4-시스 함량을 갖는 폴리부타디엔의 분자량분포 조절방법 |
| RU2141382C1 (ru) * | 1998-06-08 | 1999-11-20 | Государственное унитарное предприятие Научно-исследовательский институт синтетического каучука им.акад.С.В.Лебедева | Способ получения катализатора полимеризации и сополимеризации ненасыщенных углеводородов |
| DE19919870A1 (de) * | 1999-04-30 | 2000-11-02 | Bayer Ag | Verfahren zur Suspensions-Polymerisation von konjugierten Dienen |
| KR100305670B1 (ko) * | 1999-06-23 | 2001-09-24 | 박찬구 | 단분자 형태의 알루미늄 촉매를 이용한 높은 1,4-시스 함량을 갖는 폴리부타디엔의 제조방법 |
| KR100348763B1 (ko) | 2000-07-06 | 2002-08-13 | 금호석유화학 주식회사 | 높은 1,4-시스 함량을 갖는 폴리부타디엔의 분지도 조절방법 |
| KR100452810B1 (ko) | 2000-08-28 | 2004-10-14 | 금호석유화학 주식회사 | 조절된 분자량 및 높은 1,4-시스 함량을 갖는폴리부타디엔의 제조방법 |
| US9226876B2 (en) * | 2001-10-19 | 2016-01-05 | The Goodyear Tire & Rubber Company | Rubber for baby bottle nipples, pacifiers, and syringe plungers |
| US6780948B2 (en) | 2002-03-28 | 2004-08-24 | The Goodyear Tire & Rubber Company | Synthesis of polyisoprene with neodymium catalyst |
| US7091150B2 (en) * | 2003-12-19 | 2006-08-15 | The Goodyear Tire & Rubber Company | Synthetic polyisoprene rubber |
| FR2886937B1 (fr) * | 2005-06-14 | 2007-08-10 | Michelin Soc Tech | Procede de preparation d'un elastomere dienique, tel qu'un polybutadiene |
| EP1820789A1 (en) | 2006-02-13 | 2007-08-22 | SOLVAY (Société Anonyme) | Process for the manufacture of fluorinated alcohols |
| EP2311889A1 (de) * | 2009-10-16 | 2011-04-20 | LANXESS Deutschland GmbH | Neodym-katalysierte Polybutadiene |
| US9000107B2 (en) | 2011-01-31 | 2015-04-07 | Bridgestone Corporation | Process for producing polydienes |
| CN104204000B (zh) | 2012-02-27 | 2016-08-24 | 株式会社普利司通 | 用于制备高顺式聚二烯的方法 |
| US8695665B2 (en) | 2012-06-21 | 2014-04-15 | The Goodyear Tire & Rubber Company | Tire with composite of chafer and outer sidewall rubber layer components |
| US9399689B2 (en) * | 2012-07-04 | 2016-07-26 | Bridgestone Corporation | Method for producing polybutadiene, polybutadiene, rubber composition and tire |
| WO2016057985A1 (en) | 2014-10-10 | 2016-04-14 | Bridgestone Corporation | Polymerization catalyst composition and method of employing same |
| CN113105573A (zh) | 2015-01-28 | 2021-07-13 | 株式会社普利司通 | 具有改善的耐冷流性的顺式-1,4-聚二烯 |
| JP6717840B2 (ja) | 2015-01-28 | 2020-07-08 | 株式会社ブリヂストン | 熟成ランタニド系触媒系及びシス−１，４−ポリジエンの調製における同触媒系の使用 |
| US10202474B2 (en) | 2015-09-11 | 2019-02-12 | Bridgestone Corporation | Process for producing polydienes |
| US10066035B2 (en) | 2015-12-07 | 2018-09-04 | Bridgestone Corporation | Catalyst systems and methods for preparation of 1,4-polybutadiene rubber |
| US10730985B2 (en) | 2016-12-19 | 2020-08-04 | Bridgestone Corporation | Functionalized polymer, process for preparing and rubber compositions containing the functionalized polymer |
| JP7019818B2 (ja) | 2017-12-15 | 2022-02-15 | 株式会社ブリヂストン | 官能化ポリマー、官能化ポリマーの調製プロセス、及び官能化ポリマーを含有するゴム組成物 |
| US11512148B2 (en) | 2017-12-30 | 2022-11-29 | Bridgestone Corporation | Composition including multiple terminally functionalized polymers |
| EP3622843B1 (en) | 2018-09-13 | 2023-01-25 | The Goodyear Tire & Rubber Company | Resin modified oil extended rubber |
| EP3938412B1 (en) | 2019-03-10 | 2024-04-24 | Bridgestone Corporation | Modified high cis polydiene polymer, related methods and rubber compositions |
| US11767388B1 (en) | 2019-09-18 | 2023-09-26 | The Goodyear Tire & Rubber Company | Silicon-functionalized rubber |
| US11560462B1 (en) | 2019-09-20 | 2023-01-24 | The Goodyear Tire & Rubber Company | Functionalized high cis-1,4-polybutadiene |
| EP3838932B1 (en) | 2019-12-20 | 2022-08-10 | The Goodyear Tire & Rubber Company | Synthesis of isoprene-butadiene copolymer rubbers |
| US11584808B2 (en) | 2019-12-30 | 2023-02-21 | Bridgestone Corporation | Polymerization catalyst composition and method of employing same |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4096322A (en) * | 1974-12-23 | 1978-06-20 | The Goodyear Tire & Rubber Company | Polymerization of butadiene |
| 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 |
-
1982
- 1982-09-07 JP JP57154585A patent/JPS5945337A/ja active Granted
-
1983
- 1983-08-30 CA CA000435667A patent/CA1228697A/en not_active Expired
- 1983-09-07 US US06/530,169 patent/US4533711A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| CA1228697A (en) | 1987-10-27 |
| JPS5945337A (ja) | 1984-03-14 |
| US4533711A (en) | 1985-08-06 |
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