TWI549976B - 改質共軛二烯系聚合物、其製造方法、聚合物組成物、交聯聚合物以及輪胎 - Google Patents
改質共軛二烯系聚合物、其製造方法、聚合物組成物、交聯聚合物以及輪胎 Download PDFInfo
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- TWI549976B TWI549976B TW101148783A TW101148783A TWI549976B TW I549976 B TWI549976 B TW I549976B TW 101148783 A TW101148783 A TW 101148783A TW 101148783 A TW101148783 A TW 101148783A TW I549976 B TWI549976 B TW I549976B
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- Prior art keywords
- conjugated diene
- group
- compound
- diene polymer
- hydrocarbon group
- Prior art date
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- YNLAOSYQHBDIKW-UHFFFAOYSA-M diethylaluminium chloride Chemical compound CC[Al](Cl)CC YNLAOSYQHBDIKW-UHFFFAOYSA-M 0.000 description 1
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- 238000006138 lithiation reaction Methods 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 1
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- MOVBJUGHBJJKOW-UHFFFAOYSA-N methyl 2-amino-5-methoxybenzoate Chemical compound COC(=O)C1=CC(OC)=CC=C1N MOVBJUGHBJJKOW-UHFFFAOYSA-N 0.000 description 1
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- DZRKBPWATCKLKY-UHFFFAOYSA-N n-benzyl-n-methylprop-2-en-1-amine Chemical compound C=CCN(C)CC1=CC=CC=C1 DZRKBPWATCKLKY-UHFFFAOYSA-N 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- WGARMULIELDQEH-UHFFFAOYSA-N n-cyclohexyl-1,3-benzothiazole-2-sulfinamide Chemical compound N=1C2=CC=CC=C2SC=1S(=O)NC1CCCCC1 WGARMULIELDQEH-UHFFFAOYSA-N 0.000 description 1
- XBRUGMQPHDONFS-UHFFFAOYSA-N n-tert-butyl-1,3-benzothiazole-2-sulfinamide Chemical compound C1=CC=C2SC(S(=O)NC(C)(C)C)=NC2=C1 XBRUGMQPHDONFS-UHFFFAOYSA-N 0.000 description 1
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
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- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- PJNZPQUBCPKICU-UHFFFAOYSA-N phosphoric acid;potassium Chemical compound [K].OP(O)(O)=O PJNZPQUBCPKICU-UHFFFAOYSA-N 0.000 description 1
- PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Natural products CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 description 1
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- 239000005077 polysulfide Substances 0.000 description 1
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- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011698 potassium fluoride Substances 0.000 description 1
- 235000003270 potassium fluoride Nutrition 0.000 description 1
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Inorganic materials [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- VMULYNIDGGUNGG-UHFFFAOYSA-N propyl 2-methylthiirane-2-carboxylate Chemical compound C(C1(CS1)C)(=O)OCCC VMULYNIDGGUNGG-UHFFFAOYSA-N 0.000 description 1
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- 239000000377 silicon dioxide Substances 0.000 description 1
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- 229910052708 sodium Inorganic materials 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
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- 238000003756 stirring Methods 0.000 description 1
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 1
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- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 125000001302 tertiary amino group Chemical group 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
- 229960002447 thiram Drugs 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- IAQRGUVFOMOMEM-ONEGZZNKSA-N trans-but-2-ene Chemical compound C\C=C\C IAQRGUVFOMOMEM-ONEGZZNKSA-N 0.000 description 1
- 235000013337 tricalcium citrate Nutrition 0.000 description 1
- WVLBCYQITXONBZ-UHFFFAOYSA-N trimethyl phosphate Chemical compound COP(=O)(OC)OC WVLBCYQITXONBZ-UHFFFAOYSA-N 0.000 description 1
- ABDKAPXRBAPSQN-UHFFFAOYSA-N veratrole Chemical compound COC1=CC=CC=C1OC ABDKAPXRBAPSQN-UHFFFAOYSA-N 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
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- 239000011592 zinc chloride Substances 0.000 description 1
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- DUNKXUFBGCUVQW-UHFFFAOYSA-J zirconium tetrachloride Chemical compound Cl[Zr](Cl)(Cl)Cl DUNKXUFBGCUVQW-UHFFFAOYSA-J 0.000 description 1
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Classifications
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/42—Introducing metal atoms or metal-containing groups
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/34—Silicon-containing compounds
- C08K3/36—Silica
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B60—VEHICLES IN GENERAL
- B60C—VEHICLE TYRES; TYRE INFLATION; TYRE CHANGING; CONNECTING VALVES TO INFLATABLE ELASTIC BODIES IN GENERAL; DEVICES OR ARRANGEMENTS RELATED TO TYRES
- B60C1/00—Tyres characterised by the chemical composition or the physical arrangement or mixture of the composition
- B60C1/0016—Compositions of the tread
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B60—VEHICLES IN GENERAL
- B60C—VEHICLE TYRES; TYRE INFLATION; TYRE CHANGING; CONNECTING VALVES TO INFLATABLE ELASTIC BODIES IN GENERAL; DEVICES OR ARRANGEMENTS RELATED TO TYRES
- B60C1/00—Tyres characterised by the chemical composition or the physical arrangement or mixture of the composition
- B60C1/0025—Compositions of the sidewalls
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B60—VEHICLES IN GENERAL
- B60C—VEHICLE TYRES; TYRE INFLATION; TYRE CHANGING; CONNECTING VALVES TO INFLATABLE ELASTIC BODIES IN GENERAL; DEVICES OR ARRANGEMENTS RELATED TO TYRES
- B60C1/00—Tyres characterised by the chemical composition or the physical arrangement or mixture of the composition
- B60C1/0041—Compositions of the carcass layers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08C—TREATMENT OR CHEMICAL MODIFICATION OF RUBBERS
- C08C19/00—Chemical modification of rubber
- C08C19/22—Incorporating nitrogen atoms into the molecule
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08C—TREATMENT OR CHEMICAL MODIFICATION OF RUBBERS
- C08C19/00—Chemical modification of rubber
- C08C19/30—Addition of a reagent which reacts with a hetero atom or a group containing hetero atoms of the macromolecule
- C08C19/42—Addition of a reagent which reacts with a hetero atom or a group containing hetero atoms of the macromolecule reacting with metals or metal-containing groups
- C08C19/44—Addition of a reagent which reacts with a hetero atom or a group containing hetero atoms of the macromolecule reacting with metals or metal-containing groups of polymers containing metal atoms exclusively at one or both ends of the skeleton
-
- 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
- C08F8/00—Chemical modification by after-treatment
- C08F8/30—Introducing nitrogen atoms or nitrogen-containing groups
- C08F8/32—Introducing nitrogen atoms or nitrogen-containing groups by reaction with amines
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/02—Elements
- C08K3/04—Carbon
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L15/00—Compositions of rubber derivatives
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L91/00—Compositions of oils, fats or waxes; Compositions of derivatives thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Mechanical Engineering (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Compositions Of Macromolecular Compounds (AREA)
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| US10308746B2 (en) * | 2014-09-10 | 2019-06-04 | Sumitomo Chemical Company, Limited | Conjugated diene polymer and conjugated diene polymer composition |
| WO2016039386A1 (ja) * | 2014-09-10 | 2016-03-17 | 住友化学株式会社 | 共役ジエン重合体及び共役ジエン重合体組成物 |
| KR101653574B1 (ko) * | 2014-12-11 | 2016-09-08 | 주식회사 엘지화학 | 변성 공역디엔계 중합체, 이를 포함하는 변성 고무 조성물 및 변성 공역디엔계 중합체의 제조방법 |
| KR101759402B1 (ko) | 2014-12-11 | 2017-07-19 | 주식회사 엘지화학 | 변성 공역디엔계 중합체, 이의 제조방법, 및 이를 포함하는 고무 조성물 |
| CN107835823B (zh) | 2015-07-01 | 2021-06-18 | 株式会社普利司通 | 用官能硅烷进行末端官能化的共聚物、其组合物和相关方法 |
| WO2017026288A1 (ja) * | 2015-08-10 | 2017-02-16 | Jsr株式会社 | 共役ジエン系重合体及びその製造方法、重合体組成物、架橋重合体、並びにタイヤ |
| EP3351563B1 (en) * | 2015-09-14 | 2019-11-06 | JSR Corporation | Method for producing hydrogenated conjugated diene polymer, hydrogenated conjugated diene polymer, polymer composition, cross-linked polymer, and tire |
| CN107614506B (zh) * | 2015-11-02 | 2019-09-06 | Lg化学株式会社 | 有机锂化合物及其用途 |
| KR101997596B1 (ko) * | 2016-07-04 | 2019-07-08 | 주식회사 엘지화학 | 변성제, 변성 공액디엔계 중합체 및 이를 포함하는 고무 조성물 |
| WO2018092843A1 (ja) * | 2016-11-16 | 2018-05-24 | Jsr株式会社 | 変性共役ジエン系重合体の製造方法、変性共役ジエン系重合体、重合体組成物、架橋物及びタイヤ |
| KR102372043B1 (ko) * | 2017-08-18 | 2022-03-07 | 제이에스알 가부시끼가이샤 | 고무 조성물의 제조 방법 |
| WO2020116389A1 (ja) * | 2018-12-03 | 2020-06-11 | Jsr株式会社 | 重合体組成物、架橋体及びタイヤ |
| KR102549890B1 (ko) * | 2019-03-07 | 2023-06-29 | 가부시키가이샤 에네오스 마테리아루 | 변성 공액 디엔계 중합체의 제조 방법, 변성 공액 디엔계 중합체, 중합체 조성물, 가교체 및 타이어 |
| JP2020196803A (ja) * | 2019-05-31 | 2020-12-10 | Jsr株式会社 | 変性共役ジエン系重合体の製造方法、変性共役ジエン系重合体、重合体組成物、架橋体及びタイヤ |
| IT201900019795A1 (it) | 2019-10-25 | 2021-04-25 | Pirelli | Composizione elastomerica per mescole di pneumatici per ruote di veicoli e pneumatici che la comprendono |
| EP4431533A4 (en) * | 2021-11-10 | 2025-03-05 | ENEOS Materials Corporation | METHOD FOR PRODUCING A MODIFIED CONJUGATED DIENE POLYMER, MODIFIED CONJUGATED DIENE POLYMER, POLYMER COMPOSITION, CROSS-LINKED BODY AND TIRE |
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| CN101724127A (zh) * | 2008-10-16 | 2010-06-09 | 住友橡胶工业株式会社 | 聚合物、橡胶组合物及使用该橡胶组合物的轮胎 |
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| JP4126533B2 (ja) | 2002-06-20 | 2008-07-30 | Ｊｓｒ株式会社 | 共役ジオレフィン（共）重合ゴム、該（共）重合ゴムの製造方法、ゴム組成物およびタイヤ |
| WO2003048216A1 (en) | 2001-12-03 | 2003-06-12 | Bridgestone Corporation | Process for producing modified polymer, modified polymer obtained by the process, and rubber composition |
| JP2005290355A (ja) | 2004-03-11 | 2005-10-20 | Sumitomo Chemical Co Ltd | 変性ジエン系重合体ゴム及びその製造方法 |
| DE102005057801A1 (de) | 2005-01-20 | 2006-08-03 | Degussa Ag | Mercaptosilane |
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| CN102574932B (zh) * | 2009-10-21 | 2014-11-12 | Jsr株式会社 | 改性共轭二烯系橡胶的制造方法、改性共轭二烯系橡胶及橡胶组合物 |
| SG184296A1 (en) * | 2010-03-31 | 2012-11-29 | Jsr Corp | Process for production of modified conjugated diene rubber, modified conjugated diene rubber, and rubber composition |
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- 2012-12-19 JP JP2013550300A patent/JP5871011B2/ja active Active
- 2012-12-19 IN IN4702CHN2014 patent/IN2014CN04702A/en unknown
- 2012-12-19 KR KR1020147013312A patent/KR101938580B1/ko active Active
- 2012-12-19 BR BR112014015698A patent/BR112014015698B8/pt active IP Right Grant
- 2012-12-19 WO PCT/JP2012/082885 patent/WO2013094629A1/ja not_active Ceased
- 2012-12-19 CN CN201280063584.6A patent/CN104011093A/zh active Pending
- 2012-12-19 SG SG11201403457YA patent/SG11201403457YA/en unknown
- 2012-12-19 EP EP12859170.8A patent/EP2796479B1/en active Active
- 2012-12-19 US US14/367,533 patent/US20140357784A1/en not_active Abandoned
- 2012-12-19 HU HUE12859170A patent/HUE037617T2/hu unknown
- 2012-12-20 TW TW101148783A patent/TWI549976B/zh active
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN101724127A (zh) * | 2008-10-16 | 2010-06-09 | 住友橡胶工业株式会社 | 聚合物、橡胶组合物及使用该橡胶组合物的轮胎 |
Also Published As
| Publication number | Publication date |
|---|---|
| EP2796479A1 (en) | 2014-10-29 |
| WO2013094629A1 (ja) | 2013-06-27 |
| TW201331242A (zh) | 2013-08-01 |
| BR112014015698B1 (pt) | 2020-12-29 |
| BR112014015698B8 (pt) | 2023-04-18 |
| JP5871011B2 (ja) | 2016-03-01 |
| JPWO2013094629A1 (ja) | 2015-04-27 |
| EP2796479A4 (en) | 2015-09-02 |
| IN2014CN04702A (OSRAM) | 2015-09-18 |
| KR101938580B1 (ko) | 2019-01-15 |
| BR112014015698A2 (pt) | 2017-06-13 |
| KR20140107198A (ko) | 2014-09-04 |
| HUE037617T2 (hu) | 2018-09-28 |
| US20140357784A1 (en) | 2014-12-04 |
| SG11201403457YA (en) | 2014-09-26 |
| CN104011093A (zh) | 2014-08-27 |
| EP2796479B1 (en) | 2018-02-28 |
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