CN1610700A - 含高比例顺位双键的改性聚合物、其制备方法及其应用 - Google Patents
含高比例顺位双键的改性聚合物、其制备方法及其应用 Download PDFInfo
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- CN1610700A CN1610700A CN02812585.1A CN02812585A CN1610700A CN 1610700 A CN1610700 A CN 1610700A CN 02812585 A CN02812585 A CN 02812585A CN 1610700 A CN1610700 A CN 1610700A
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- 239000011952 anionic catalyst Substances 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- IMJGQTCMUZMLRZ-UHFFFAOYSA-N buta-1,3-dien-2-ylbenzene Chemical compound C=CC(=C)C1=CC=CC=C1 IMJGQTCMUZMLRZ-UHFFFAOYSA-N 0.000 description 1
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 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 description 1
- 230000008859 change Effects 0.000 description 1
- KOPOQZFJUQMUML-UHFFFAOYSA-N chlorosilane Chemical compound Cl[SiH3] KOPOQZFJUQMUML-UHFFFAOYSA-N 0.000 description 1
- KQWGXHWJMSMDJJ-UHFFFAOYSA-N cyclohexyl isocyanate Chemical group O=C=NC1CCCCC1 KQWGXHWJMSMDJJ-UHFFFAOYSA-N 0.000 description 1
- 229920003244 diene elastomer Polymers 0.000 description 1
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- WUDNUHPRLBTKOJ-UHFFFAOYSA-N ethyl isocyanate Chemical group CCN=C=O WUDNUHPRLBTKOJ-UHFFFAOYSA-N 0.000 description 1
- SBRXLTRZCJVAPH-UHFFFAOYSA-N ethyl(trimethoxy)silane Chemical compound CC[Si](OC)(OC)OC SBRXLTRZCJVAPH-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000012690 ionic polymerization Methods 0.000 description 1
- IHLVCKWPAMTVTG-UHFFFAOYSA-N lithium;carbanide Chemical compound [Li+].[CH3-] IHLVCKWPAMTVTG-UHFFFAOYSA-N 0.000 description 1
- CETVQRFGPOGIQJ-UHFFFAOYSA-N lithium;hexane Chemical compound [Li+].CCCCC[CH2-] CETVQRFGPOGIQJ-UHFFFAOYSA-N 0.000 description 1
- IQIWJEAPUNWDLC-UHFFFAOYSA-N lithium;octane Chemical compound [Li+].CCCCCCC[CH2-] IQIWJEAPUNWDLC-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- DIHKMUNUGQVFES-UHFFFAOYSA-N n,n,n',n'-tetraethylethane-1,2-diamine Chemical compound CCN(CC)CCN(CC)CC DIHKMUNUGQVFES-UHFFFAOYSA-N 0.000 description 1
- 150000002798 neodymium compounds Chemical class 0.000 description 1
- ARWCRSVRKCNEDI-UHFFFAOYSA-K neodymium(3+);octanoate Chemical compound [Nd+3].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O.CCCCCCCC([O-])=O ARWCRSVRKCNEDI-UHFFFAOYSA-K 0.000 description 1
- 150000003961 organosilicon compounds Chemical group 0.000 description 1
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 229940031826 phenolate Drugs 0.000 description 1
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical group ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 1
- 230000008845 photoaging Effects 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Natural products CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 238000000710 polymer precipitation Methods 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229960001866 silicon dioxide Drugs 0.000 description 1
- FDNAPBUWERUEDA-UHFFFAOYSA-N silicon tetrachloride Chemical group Cl[Si](Cl)(Cl)Cl FDNAPBUWERUEDA-UHFFFAOYSA-N 0.000 description 1
- 125000005373 siloxane group Chemical group [SiH2](O*)* 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- SLRCCWJSBJZJBV-AJNGGQMLSA-N sparteine Chemical compound C1N2CCCC[C@H]2[C@@H]2CN3CCCC[C@H]3[C@H]1C2 SLRCCWJSBJZJBV-AJNGGQMLSA-N 0.000 description 1
- 229960001945 sparteine Drugs 0.000 description 1
- 230000003019 stabilising effect Effects 0.000 description 1
- 238000007655 standard test method Methods 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 208000011117 substance-related disease Diseases 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 125000000101 thioether group Chemical group 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical group Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 description 1
- MCULRUJILOGHCJ-UHFFFAOYSA-N triisobutylaluminium Chemical compound CC(C)C[Al](CC(C)C)CC(C)C MCULRUJILOGHCJ-UHFFFAOYSA-N 0.000 description 1
- 238000004073 vulcanization Methods 0.000 description 1
Classifications
-
- 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
-
- 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
- C08C19/26—Incorporating metal atoms into the molecule
Landscapes
- Chemical & Material Sciences (AREA)
- General 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)
Abstract
Description
微结构 | GPC | DSC | 元素分析 | ||||||||
ML1+4 | 改性前溶液粘度 | 改性后溶液粘度 | 顺式 | 反式 | 乙烯基 | Mw | Mn | 多分散性 | Tg | N | |
ME | mPas | mPas | % | % | % | g/mole | g/mole | ℃ | ppm | ||
a) | 46 | 488 | 174 | 97.0 | 1.8 | 1.2 | 633490 | 183126 | 3.5 | -104.7 | 230 |
b) | 41 | 441 | 145 | 98.0 | 1.5 | 0.4 | 643426 | 172296 | 3.7 | -106.8 | 329 |
微结构 | GPC | DSC | |||||||
ML1+4 | 改性前溶液粘度 | 改性后溶液粘度 | 顺式 | 反式 | 乙烯基 | Mw | Mn | 多分散性 | Tg |
ME | mPas | mPas | % | % | % | g/mole | g/mole | ℃ | |
60 | 1587 | 378 | 98.5 | 1.0 | 0.5 | 790128 | 244375 | 3.20 | -100.7 |
微结构 | GPC | DSC | 元素分析 | |||||||
ML1+4 | 改性前溶液粘度 | 改性后溶液粘度 | 顺式 | 反式 | 乙烯基 | Mw | Mn | 多分散性 | Tg | C1 |
ME | mPas | mPas | % | % | % | g/mole | g/mole | ℃ | % | |
48 | 741 | 429 | 98.2 | 1.3 | 0.5 | 634378 | 182.396 | 3.5 | -105.3 | 0.06 |
微结构 | GPC | DSC | |||||||
ML1+4 | 改性前溶液粘度 | 改性后溶液粘度 | 顺式 | 反式 | 乙烯基 | Mw | Mn | 多分散性 | Tg |
ME | mPas | mPas | % | % | % | g/mole | g/mole | ℃ | |
41 | 827 | 554 | 97.0 | 1.8 | 1.2 | 584330 | 171862 | 3.4 | -104.9 |
1,4比例(wt.%) | 1,2比例(wt.%) | 元素分析(N2,ppm) | TG[℃] | 门尼粘度(M1 1+4,100℃) | 分子量(GPC,g/mole) |
92 | 7.8 | 101 | -85 | 53 | 283,000 |
极性LiBRa) | 极性NdBR1b) | 极性NdBR2c) | |
Buna VSL 5025-0 HM(LSBR) | 54 | 54 | 54 |
TSR 5,Defo 700(NR) | 10 | 10 | 10 |
极性改性LiBR | 36 | 0 | 0 |
极性改性NdBR1 | 0 | 36 | 0 |
极性改性NdBR2 | 0 | 0 | 36 |
矿物油* | 37.5 | 37.5 | 37.5 |
Vulkasil S******** | 70 | 70 | 70 |
硅烷Si 69********* | 5.6 | 5.6 | 5.6 |
ZnO RS | 2.5 | 2.5 | 2.5 |
硬脂酸 | 1 | 1 | 1 |
Antilux 654** | 1.5 | 1.5 | 1.5 |
Vulkanox HS**** | 1 | 1 | 1 |
Vulkanox 4020*** | 1 | 1 | 1 |
Vulkacit CZ****** | 1.8 | 1.8 | 1.8 |
Vulkacit D******* | 2 | 2 | 2 |
硫 | 1.5 | 1.5 | 1.5 |
混合物性能,DIN 53523 | |||
>200 | 67 | 61 | |
门尼粘度ML1+4@在100℃下 | |||
硫化性能,ISO 37 | |||
强度,MPa | 16.8 | 16.5 | 18.5 |
断裂伸长,% | 260 | 486 | 532 |
应力值100%,MPa | 5.1 | 2.3 | 2.3 |
应力值300%,MPa | n.m. | 8.3 | 8.1 |
硬度23℃,Shore A | 66 | 62 | 63 |
硬度70℃,Shore A 70 | 65 | 62 | 62 |
弹性23℃,% | 32 | 41 | 42 |
弹性70℃,% | 48 | 58 | 58 |
极性LiBRa) | 极性NdBR1b) | 极性NdBR2c) |
tan delta-20℃ | 0.573 | 0.606 | 0.619 |
0 | 0.372 | 0.317 | 0.314 |
23 | 0.228 | 0.182 | 0.167 |
60 | 0.132 | 0.110 | 0.106 |
极性LiBRa) | 极性NdBR1b) | 极性NdBR2c) | 极性NdBR3d) | 极性NdBR4e) | |
Buna VSL 5025-0 HM(LSBR) | 60 | 60 | 60 | 60 | 60 |
极性改性LiBR | 40 | 0 | 0 | 0 | 0 |
极性改性NdBR1 | 0 | 40 | 0 | 0 | 0 |
极性改性NdBR2 | 0 | 0 | 40 | 0 | 0 |
极性改性NdBR3 | 0 | 0 | 0 | 40 | 0 |
极性改性NdBR4 | 0 | 0 | 0 | 0 | 40 |
Carbon black N 234 | 50 | 50 | 50 | 50 | 50 |
矿物油* | 5 | 5 | 5 | 5 | 5 |
ZnO RS | 3 | 3 | 3 | 3 | 3 |
硬脂酸 | 2 | 2 | 2 | 2 | 2 |
Antilux 654** | 1.5 | 1.5 | 1.5 | 1.5 | 1.5 |
Vulkanox HS**** | 1 | 1 | 1 | 1 | 1 |
Vulkanox 4020*** | 1 | 1 | 1 | 1 | 1 |
Vulkacit CZ****** | 1.4 | 1.4 | 1.4 | 1.4 | 1.4 |
Vulkacit D******* | 0.3 | 0.3 | 0.3 | 0.3 | 0.3 |
硫 | 1.8 | 1.8 | 1.8 | 1.8 | 1.8 |
极性LiBRa) | 极性NdBR1b) | 极性NdBR2c) | 极性NdBR3d) | 极性NdBR4e) | |
混合物性能, DIN 53523 | |||||
门尼粘度 ML1+4@在100℃ | 114 | 93 | 83 | 81 | 82 |
强度,MPa | 18.5 | 20.2 | 21.2 | 22.49 | 22.94 |
断裂伸长,% | 310 | 376 | 425 | 443 | 427 |
应力值100%,MPa | 3.8 | 2.9 | 2.7 | 2.62 | 2.6 |
应力值300%,MPa | 16.4 | 14.8 | 12.9 | 13.25 | 14.1 |
硬度23℃,Shore A | 67 | 68 | 68 | 66.1 | 68.2 |
硬度70℃,Shore A 70 | 62 | 64 | 63 | 63.6 | 65.4 |
弹性23℃,% | 37 | 42 | 39 | 45.6 | 49.6 |
弹性70℃,% | 45 | 56 | 54 | 52.6 | 54.5 |
tan delta-20℃ | 0.352 | 0.475 | 0.456 | 0.393 | 0.373 |
0℃ | 0.277 | 0.274 | 0.28 | 0.236 | 0.21 |
23℃ | 0.210 | 0.198 | 0.201 | 0.187 | 0.169 |
60℃ | 0.163 | 0.145 | 0.144 | 0.141 | 0.13 |
极性改性NdBR1 | N,N-二甲基脲酰氯 |
极性改性NdBR2 | 吗啉酰氯 |
极性改性NdBR3 | 环氧化豆油 |
极性改性NdBR4 | 表氯醇 |
极性改性LiBR | 吗啉-N-羧酸酰氯 |
Claims (3)
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE10119745 | 2001-04-23 | ||
DE10119745.4 | 2001-04-23 | ||
DE10151391A DE10151391A1 (de) | 2001-04-23 | 2001-10-18 | Modifizierte Polymere mit einem hohen Anteil an cis-ständigen Doppelbindungen, ein Verfahren zu deren Herstellung sowie deren Verwendung |
DE10151391.7 | 2001-10-18 | ||
PCT/EP2002/004038 WO2002085952A2 (de) | 2001-04-23 | 2002-04-11 | Modifizierte polymere mit einem hohen anteil an cis-ständigen doppelbindungen, ein verfahren zu deren herstellung sowie deren verwendung |
Publications (2)
Publication Number | Publication Date |
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CN1610700A true CN1610700A (zh) | 2005-04-27 |
CN1326884C CN1326884C (zh) | 2007-07-18 |
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CNB028125851A Expired - Fee Related CN1326884C (zh) | 2001-04-23 | 2002-04-11 | 含高比例顺位双键的改性聚合物、其制备方法及其应用 |
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Country | Link |
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US (1) | US6759497B2 (zh) |
EP (1) | EP1397390B1 (zh) |
JP (1) | JP2004525232A (zh) |
CN (1) | CN1326884C (zh) |
BR (1) | BR0209112A (zh) |
CA (1) | CA2444713A1 (zh) |
DE (1) | DE50211520D1 (zh) |
ES (1) | ES2298372T3 (zh) |
MX (1) | MXPA03009630A (zh) |
TW (1) | TW588053B (zh) |
WO (1) | WO2002085952A2 (zh) |
Cited By (1)
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CN101600736B (zh) * | 2006-12-27 | 2012-11-07 | Jsr株式会社 | 改性共轭二烯系聚合物的制造方法、改性共轭二烯系聚合物及橡胶组合物 |
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JP6485519B1 (ja) * | 2017-10-24 | 2019-03-20 | 横浜ゴム株式会社 | ゴム組成物、ヘテロ環変性グリセリン脂肪酸エステル及びヘテロ環変性グリセリン脂肪酸エステルの製造方法 |
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US12103334B2 (en) | 2018-05-04 | 2024-10-01 | Bridgestone Americas Tire Operations, Llc | Tire tread rubber composition |
JP2021523264A (ja) | 2018-05-04 | 2021-09-02 | ブリヂストン アメリカズ タイヤ オペレーションズ、 エルエルシー | タイヤトレッドゴム組成物 |
CN113906058B (zh) * | 2019-05-07 | 2024-05-17 | 普利司通美国轮胎运营有限责任公司 | 改性的高顺式聚丁二烯聚合物、相关方法和橡胶组合物 |
US12264232B2 (en) | 2019-05-14 | 2025-04-01 | Bridgestone Corporation | Modified high-cis polybutadiene polymer, related methods and tire components |
US12365787B2 (en) | 2019-05-29 | 2025-07-22 | Bridgestone Americas Tire Operations, Llc | Tire tread rubber composition and related methods |
JP2022534568A (ja) | 2019-05-29 | 2022-08-02 | ブリヂストン アメリカズ タイヤ オペレーションズ、 エルエルシー | タイヤトレッドゴム組成物及びその関連方法 |
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GB1173508A (en) * | 1966-08-30 | 1969-12-10 | Asahi Chemical Ind | Process for Preparing High Molecular Active Matrices. |
US3925511A (en) * | 1973-08-27 | 1975-12-09 | Uniroyal Inc | Metallation of polymers and subsequent reaction to form modified or grafted polymers |
US3978161A (en) * | 1973-10-01 | 1976-08-31 | The General Tire & Rubber Company | Metalation of polymers |
DE2848964A1 (de) | 1978-11-11 | 1980-05-22 | Bayer Ag | Katalysator, dessen herstellung und verwendung zur loesungspolymerisation von butadien |
US4761456A (en) * | 1985-06-17 | 1988-08-02 | The Dow Chemical Company | Process for metallating nonconjugated diene-containing ethylene polymers and graft polymers prepared therefrom |
EP1050545B1 (fr) * | 1999-05-05 | 2004-11-03 | Société de Technologie Michelin | Procédé de préparation de polymères qui comportent au moins une double liaison et qui présentent des fonctions à radical carbonyle le long de leur chaine |
DE19939842A1 (de) | 1999-08-23 | 2001-03-01 | Bayer Ag | Verfahren zur Copolymerisation von konjugierten Diolefinen (Dienen) und vinylaromatischen Monomeren mit Katalysatoren der Seltenen Erden sowie die Verwendung der Copolymerisate in Kautschukmischungen für Reifenanwendungen |
DE19951841A1 (de) | 1999-10-28 | 2001-05-03 | Bayer Ag | Katalysator auf Basis von Verbindungen der Seltenen Erdmetalle |
EP1162231B1 (en) * | 2000-06-08 | 2011-06-22 | Ube Industries, Ltd. | Polybutadiene and process for producing the same |
CA2420265A1 (en) * | 2000-08-23 | 2003-02-20 | Bayer Aktiengesellschaft | Metallized unsaturated polymer anions, stabilized by a coordinate bond and having a large portion of cis double bonds |
-
2002
- 2002-04-11 CN CNB028125851A patent/CN1326884C/zh not_active Expired - Fee Related
- 2002-04-11 CA CA002444713A patent/CA2444713A1/en not_active Abandoned
- 2002-04-11 ES ES02740463T patent/ES2298372T3/es not_active Expired - Lifetime
- 2002-04-11 EP EP02740463A patent/EP1397390B1/de not_active Expired - Lifetime
- 2002-04-11 DE DE50211520T patent/DE50211520D1/de not_active Expired - Lifetime
- 2002-04-11 MX MXPA03009630A patent/MXPA03009630A/es active IP Right Grant
- 2002-04-11 BR BR0209112-7A patent/BR0209112A/pt not_active Application Discontinuation
- 2002-04-11 WO PCT/EP2002/004038 patent/WO2002085952A2/de active IP Right Grant
- 2002-04-11 JP JP2002583478A patent/JP2004525232A/ja active Pending
- 2002-04-18 US US10/125,111 patent/US6759497B2/en not_active Expired - Lifetime
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Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101600736B (zh) * | 2006-12-27 | 2012-11-07 | Jsr株式会社 | 改性共轭二烯系聚合物的制造方法、改性共轭二烯系聚合物及橡胶组合物 |
Also Published As
Publication number | Publication date |
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WO2002085952A3 (de) | 2003-03-13 |
EP1397390A2 (de) | 2004-03-17 |
BR0209112A (pt) | 2004-07-13 |
WO2002085952A2 (de) | 2002-10-31 |
CN1326884C (zh) | 2007-07-18 |
DE50211520D1 (de) | 2008-02-21 |
US20030069365A1 (en) | 2003-04-10 |
CA2444713A1 (en) | 2002-10-31 |
MXPA03009630A (es) | 2004-06-30 |
HK1077307A1 (zh) | 2006-02-10 |
JP2004525232A (ja) | 2004-08-19 |
EP1397390B1 (de) | 2008-01-09 |
US6759497B2 (en) | 2004-07-06 |
ES2298372T3 (es) | 2008-05-16 |
TW588053B (en) | 2004-05-21 |
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