JP2006193577A - ポリマーの変性方法 - Google Patents
ポリマーの変性方法 Download PDFInfo
- Publication number
- JP2006193577A JP2006193577A JP2005005028A JP2005005028A JP2006193577A JP 2006193577 A JP2006193577 A JP 2006193577A JP 2005005028 A JP2005005028 A JP 2005005028A JP 2005005028 A JP2005005028 A JP 2005005028A JP 2006193577 A JP2006193577 A JP 2006193577A
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- polymer
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- Granted
Links
- 229920000642 polymer Polymers 0.000 title claims abstract description 69
- 238000000034 method Methods 0.000 title claims abstract description 21
- 150000003254 radicals Chemical class 0.000 claims abstract description 37
- -1 nitroxide radical Chemical class 0.000 claims abstract description 27
- 239000003999 initiator Substances 0.000 claims abstract description 20
- 150000001875 compounds Chemical class 0.000 claims abstract description 16
- 150000001723 carbon free-radicals Chemical class 0.000 claims abstract description 10
- 239000000203 mixture Substances 0.000 claims abstract description 7
- 229920005549 butyl rubber Polymers 0.000 claims description 7
- 239000000470 constituent Substances 0.000 claims description 2
- 238000002715 modification method Methods 0.000 claims 1
- 125000000524 functional group Chemical group 0.000 abstract description 15
- 229920001971 elastomer Polymers 0.000 abstract description 7
- 125000000962 organic group Chemical group 0.000 abstract description 5
- 229920001577 copolymer Polymers 0.000 description 6
- 0 CC(C)(CC(*)CC1(C)C)*1[O+] Chemical compound CC(C)(CC(*)CC1(C)C)*1[O+] 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- GDOPTJXRTPNYNR-UHFFFAOYSA-N methyl-cyclopentane Natural products CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 description 5
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 4
- 230000007423 decrease Effects 0.000 description 4
- 229920001519 homopolymer Polymers 0.000 description 4
- 238000012986 modification Methods 0.000 description 4
- 230000004048 modification Effects 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- 239000004342 Benzoyl peroxide Substances 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000000853 adhesive Substances 0.000 description 3
- 230000001070 adhesive effect Effects 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 229920002725 thermoplastic elastomer Polymers 0.000 description 3
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 description 2
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 2
- WYGWHHGCAGTUCH-UHFFFAOYSA-N 2-[(2-cyano-4-methylpentan-2-yl)diazenyl]-2,4-dimethylpentanenitrile Chemical compound CC(C)CC(C)(C#N)N=NC(C)(C#N)CC(C)C WYGWHHGCAGTUCH-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 239000004156 Azodicarbonamide Substances 0.000 description 2
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 2
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- KYIKRXIYLAGAKQ-UHFFFAOYSA-N abcn Chemical compound C1CCCCC1(C#N)N=NC1(C#N)CCCCC1 KYIKRXIYLAGAKQ-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000005370 alkoxysilyl group Chemical group 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 125000003368 amide group Chemical group 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- XOZUGNYVDXMRKW-AATRIKPKSA-N azodicarbonamide Chemical compound NC(=O)\N=N\C(N)=O XOZUGNYVDXMRKW-AATRIKPKSA-N 0.000 description 2
- 235000019399 azodicarbonamide Nutrition 0.000 description 2
- 235000019400 benzoyl peroxide Nutrition 0.000 description 2
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 2
- RLDQYSHDFVSAPL-UHFFFAOYSA-L calcium;dithiocyanate Chemical group [Ca+2].[S-]C#N.[S-]C#N RLDQYSHDFVSAPL-UHFFFAOYSA-L 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 239000003431 cross linking reagent Substances 0.000 description 2
- 238000006356 dehydrogenation reaction Methods 0.000 description 2
- 125000003700 epoxy group Chemical group 0.000 description 2
- 125000004185 ester group Chemical group 0.000 description 2
- 238000005227 gel permeation chromatography Methods 0.000 description 2
- VANNPISTIUFMLH-UHFFFAOYSA-N glutaric anhydride Chemical compound O=C1CCCC(=O)O1 VANNPISTIUFMLH-UHFFFAOYSA-N 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 125000005462 imide group Chemical group 0.000 description 2
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 2
- 238000004898 kneading Methods 0.000 description 2
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 125000002560 nitrile group Chemical group 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 229920002647 polyamide Polymers 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 229920000098 polyolefin Polymers 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 229940014800 succinic anhydride Drugs 0.000 description 2
- 125000001730 thiiranyl group Chemical group 0.000 description 2
- 125000003396 thiol group Chemical group [H]S* 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- 238000004073 vulcanization Methods 0.000 description 2
- WRXCBRHBHGNNQA-UHFFFAOYSA-N (2,4-dichlorobenzoyl) 2,4-dichlorobenzenecarboperoxoate Chemical compound ClC1=CC(Cl)=CC=C1C(=O)OOC(=O)C1=CC=C(Cl)C=C1Cl WRXCBRHBHGNNQA-UHFFFAOYSA-N 0.000 description 1
- QEQBMZQFDDDTPN-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy benzenecarboperoxoate Chemical compound CC(C)(C)OOOC(=O)C1=CC=CC=C1 QEQBMZQFDDDTPN-UHFFFAOYSA-N 0.000 description 1
- NALFRYPTRXKZPN-UHFFFAOYSA-N 1,1-bis(tert-butylperoxy)-3,3,5-trimethylcyclohexane Chemical compound CC1CC(C)(C)CC(OOC(C)(C)C)(OOC(C)(C)C)C1 NALFRYPTRXKZPN-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- HQOVXPHOJANJBR-UHFFFAOYSA-N 2,2-bis(tert-butylperoxy)butane Chemical compound CC(C)(C)OOC(C)(CC)OOC(C)(C)C HQOVXPHOJANJBR-UHFFFAOYSA-N 0.000 description 1
- PFHOSZAOXCYAGJ-UHFFFAOYSA-N 2-[(2-cyano-4-methoxy-4-methylpentan-2-yl)diazenyl]-4-methoxy-2,4-dimethylpentanenitrile Chemical compound COC(C)(C)CC(C)(C#N)N=NC(C)(C#N)CC(C)(C)OC PFHOSZAOXCYAGJ-UHFFFAOYSA-N 0.000 description 1
- BIISIZOQPWZPPS-UHFFFAOYSA-N 2-tert-butylperoxypropan-2-ylbenzene Chemical compound CC(C)(C)OOC(C)(C)C1=CC=CC=C1 BIISIZOQPWZPPS-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 229920002943 EPDM rubber Polymers 0.000 description 1
- 102100020870 La-related protein 6 Human genes 0.000 description 1
- 108050008265 La-related protein 6 Proteins 0.000 description 1
- 229920002367 Polyisobutene Polymers 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 230000002292 Radical scavenging effect Effects 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000013466 adhesive and sealant Substances 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000003712 anti-aging effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229920005557 bromobutyl Polymers 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000004925 denaturation Methods 0.000 description 1
- 230000036425 denaturation Effects 0.000 description 1
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 1
- 229920003244 diene elastomer Polymers 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- HQQADJVZYDDRJT-UHFFFAOYSA-N ethene;prop-1-ene Chemical group C=C.CC=C HQQADJVZYDDRJT-UHFFFAOYSA-N 0.000 description 1
- 229920005677 ethylene-propylene-butene terpolymer Polymers 0.000 description 1
- 229920001973 fluoroelastomer Polymers 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 1
- 239000012943 hotmelt Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- ZQMHJBXHRFJKOT-UHFFFAOYSA-N methyl 2-[(1-methoxy-2-methyl-1-oxopropan-2-yl)diazenyl]-2-methylpropanoate Chemical compound COC(=O)C(C)(C)N=NC(C)(C)C(=O)OC ZQMHJBXHRFJKOT-UHFFFAOYSA-N 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920001083 polybutene Polymers 0.000 description 1
- 229920006124 polyolefin elastomer Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920002742 polystyrene-block-poly(ethylene/propylene) -block-polystyrene Polymers 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 239000012763 reinforcing filler Substances 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 239000000565 sealant Substances 0.000 description 1
- 239000003566 sealing material Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229920001935 styrene-ethylene-butadiene-styrene Polymers 0.000 description 1
- 229920001897 terpolymer Polymers 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 229920005992 thermoplastic resin Polymers 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- KAKZBPTYRLMSJV-UHFFFAOYSA-N vinyl-ethylene Natural products C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 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
- C08F8/00—Chemical modification by after-treatment
- C08F8/50—Partial depolymerisation
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)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
【解決手段】 分子内の炭素ラジカルにより分解するポリマーに、ラジカル開始剤及び分子内にニトロキシドラジカルを有する化合物を反応させて変性を行うことによりポリマーの分子量を低下させ、かつポリマー中に前記フリーラジカルに由来する有機基を導入することを特徴とするポリマーの変性方法並びにそれによって得られる変性ポリマー及びそれを含むゴム組成物。
【選択図】 なし
Description
表Iに示す量(重量部)のブチルゴム、ラジカル開始剤及び2,2,6,6−テトラメチルピペリジニル−1−オキシル誘導体(OH−TEMPO)もしくはグリシジルメタクリレート(GMA)量を60℃に温度を設定した密閉型バンバリーに入れ、15分間混合した。得られた混合物を、100℃に温度設定した密閉型バンバリー中で混練しながら5分間窒素置換した。混練しながら、温度を表Iに示した温度まで上昇させ、その温度で15分間混錬した。
Claims (6)
- 分子内の炭素ラジカルにより分解するポリマーに、ラジカル開始剤及び分子内にニトロキシドラジカルを有する化合物を反応させて変性を行うことによりポリマーの分子量を低下させ、かつポリマー中に前記フリーラジカルに由来する有機基を導入することを特徴とするポリマーの変性方法。
- 前記ニトロキシドラジカルとラジカル開始剤のモル比(ニトロキシドラジカル/ラジカル開始剤)が0.7未満である請求項1に記載のポリマーの変性方法。
- 前記ポリマーがその構成単位中にイソモノオレフィン単位を含むポリマーである請求項1又は2に記載のポリマーの変性方法。
- 構成単位中にイソモノオレフィン単位を含む前記ポリマーがブチルゴムである請求項3に記載のポリマーの変性方法。
- 請求項1〜4のいずれか1項の変性方法により得られる変性ポリマー。
- 請求項5に記載の変性ポリマーを含むポリマー組成物。
Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2005005028A JP3963917B2 (ja) | 2005-01-12 | 2005-01-12 | ポリマーの変性方法 |
US11/329,082 US7282542B2 (en) | 2005-01-12 | 2006-01-11 | Modification method of polymer |
DE102006001483A DE102006001483B4 (de) | 2005-01-12 | 2006-01-11 | Verfahren zum Modifizieren eines Polymers |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2005005028A JP3963917B2 (ja) | 2005-01-12 | 2005-01-12 | ポリマーの変性方法 |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2006193577A true JP2006193577A (ja) | 2006-07-27 |
JP3963917B2 JP3963917B2 (ja) | 2007-08-22 |
Family
ID=36643240
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2005005028A Active JP3963917B2 (ja) | 2005-01-12 | 2005-01-12 | ポリマーの変性方法 |
Country Status (3)
Country | Link |
---|---|
US (1) | US7282542B2 (ja) |
JP (1) | JP3963917B2 (ja) |
DE (1) | DE102006001483B4 (ja) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7772325B2 (en) | 2006-12-13 | 2010-08-10 | The Yokohama Rubber Co., Ltd. | Thermoplastic elastomer composition |
WO2011138890A1 (ja) * | 2010-05-07 | 2011-11-10 | 横浜ゴム株式会社 | 変性ポリマーの製造法 |
JP2012126380A (ja) * | 2010-11-25 | 2012-07-05 | Yokohama Rubber Co Ltd:The | 空気入りタイヤ及びその製造方法 |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20080087380A1 (en) * | 2006-10-13 | 2008-04-17 | Dow Global Technologies Inc. | Reactively-coupled articles and related methods |
JP4236686B2 (ja) * | 2007-04-19 | 2009-03-11 | 横浜ゴム株式会社 | 変性ブチルゴム組成物 |
JP4420095B2 (ja) * | 2007-10-01 | 2010-02-24 | 横浜ゴム株式会社 | 変性ブチルゴム組成物 |
Family Cites Families (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3486145T2 (de) * | 1983-07-11 | 1993-09-23 | Commw Scient Ind Res Org | Verfahren zur polymerisation und nach diesem verfahren hergestellte polymere. |
FR2730240A1 (fr) * | 1995-02-07 | 1996-08-09 | Atochem Elf Sa | Stabilisation d'un polymere par un radical libre stable |
DE69727550T2 (de) * | 1996-10-25 | 2004-12-23 | The Yokohama Rubber Co., Ltd. | Gummizusammensetzung |
JPH10182881A (ja) | 1996-10-25 | 1998-07-07 | Yokohama Rubber Co Ltd:The | ゴム組成物 |
US6372855B1 (en) * | 1998-08-31 | 2002-04-16 | The Yokohama Rubber Co., Ltd. | Polymer containing isobutylene as repeating unit and rubber composition containing the same |
US6177519B1 (en) * | 1999-03-02 | 2001-01-23 | Exxon Chemical Patents, Inc. | Silane grafted copolymers of an isomonoolefin and a vinyl aromatic monomer |
FR2805268B1 (fr) * | 2000-02-23 | 2005-03-25 | Atofina | Polymeres thermoreversibles a fonctions mitroxyde |
US7030196B2 (en) * | 2000-05-19 | 2006-04-18 | Ciba Specialty Chemicals Corporation | Process for reducing the molecular weight of polypropylene |
US6767940B2 (en) * | 2002-07-25 | 2004-07-27 | Acushnet Company | Golf ball compositions comprising stable free radicals |
JP2004311135A (ja) | 2003-04-04 | 2004-11-04 | Japan Atom Energy Res Inst | カーボンナノチューブを用いた負イオン源 |
JP4101242B2 (ja) | 2004-04-01 | 2008-06-18 | 横浜ゴム株式会社 | ポリマーの変性方法 |
US7820732B2 (en) * | 2004-04-30 | 2010-10-26 | Advanced Cardiovascular Systems, Inc. | Methods for modulating thermal and mechanical properties of coatings on implantable devices |
-
2005
- 2005-01-12 JP JP2005005028A patent/JP3963917B2/ja active Active
-
2006
- 2006-01-11 US US11/329,082 patent/US7282542B2/en not_active Expired - Fee Related
- 2006-01-11 DE DE102006001483A patent/DE102006001483B4/de not_active Expired - Fee Related
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7772325B2 (en) | 2006-12-13 | 2010-08-10 | The Yokohama Rubber Co., Ltd. | Thermoplastic elastomer composition |
WO2011138890A1 (ja) * | 2010-05-07 | 2011-11-10 | 横浜ゴム株式会社 | 変性ポリマーの製造法 |
JP2011236280A (ja) * | 2010-05-07 | 2011-11-24 | Yokohama Rubber Co Ltd:The | 変性ポリマーの製造法 |
US8557926B2 (en) | 2010-05-07 | 2013-10-15 | The Yokohama Rubber Co., Ltd. | Method for producing modified polymer |
KR101322685B1 (ko) * | 2010-05-07 | 2013-10-30 | 요코하마 고무 가부시키가이샤 | 변성 폴리머의 제조법 |
JP2012126380A (ja) * | 2010-11-25 | 2012-07-05 | Yokohama Rubber Co Ltd:The | 空気入りタイヤ及びその製造方法 |
Also Published As
Publication number | Publication date |
---|---|
DE102006001483B4 (de) | 2008-12-24 |
DE102006001483A1 (de) | 2006-07-20 |
US7282542B2 (en) | 2007-10-16 |
US20060155079A1 (en) | 2006-07-13 |
JP3963917B2 (ja) | 2007-08-22 |
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