JP2010536946A - 共役ジエンをベースとした、または共役ジエンおよびビニル芳香族化合物をベースとした変性ポリマー、その調製方法、およびその使用 - Google Patents
共役ジエンをベースとした、または共役ジエンおよびビニル芳香族化合物をベースとした変性ポリマー、その調製方法、およびその使用 Download PDFInfo
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- JP2010536946A JP2010536946A JP2010520544A JP2010520544A JP2010536946A JP 2010536946 A JP2010536946 A JP 2010536946A JP 2010520544 A JP2010520544 A JP 2010520544A JP 2010520544 A JP2010520544 A JP 2010520544A JP 2010536946 A JP2010536946 A JP 2010536946A
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- conjugated dienes
- diisocyanate
- compounds
- polymer according
- modified polymer
- Prior art date
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- 239000004814 polyurethane Substances 0.000 claims description 21
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- 239000000178 monomer Substances 0.000 claims description 10
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- NONOKGVFTBWRLD-UHFFFAOYSA-N thioisocyanate group Chemical group S(N=C=O)N=C=O NONOKGVFTBWRLD-UHFFFAOYSA-N 0.000 claims description 7
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- 150000001412 amines Chemical class 0.000 claims description 5
- KORSJDCBLAPZEQ-UHFFFAOYSA-N dicyclohexylmethane-4,4'-diisocyanate Chemical compound C1CC(N=C=O)CCC1CC1CCC(N=C=O)CC1 KORSJDCBLAPZEQ-UHFFFAOYSA-N 0.000 claims description 5
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- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical group C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 claims description 2
- UGWOAPBVIGCNOV-UHFFFAOYSA-N 5-ethenyldec-5-ene Chemical compound CCCCC=C(C=C)CCCC UGWOAPBVIGCNOV-UHFFFAOYSA-N 0.000 claims description 2
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- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 claims description 2
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- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 claims 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 35
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- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
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- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- AAHLLMGAWIHICC-UHFFFAOYSA-N N-hydroxy-3-[4-[[2-(2-methyl-1H-indol-3-yl)ethylamino]methyl]phenyl]propanamide Chemical compound Cc1[nH]c2ccccc2c1CCNCc1ccc(CCC(=O)NO)cc1 AAHLLMGAWIHICC-UHFFFAOYSA-N 0.000 description 2
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- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 2
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- 238000004519 manufacturing process Methods 0.000 description 2
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- AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- AVWRKZWQTYIKIY-UHFFFAOYSA-N urea-1-carboxylic acid Chemical group NC(=O)NC(O)=O AVWRKZWQTYIKIY-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 238000010626 work up procedure Methods 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
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/67—Unsaturated compounds having active hydrogen
- C08G18/69—Polymers of conjugated dienes
- C08G18/696—Polymers of conjugated dienes containing heteroatoms other than oxygen and other than the heteroatoms of copolymerised vinyl monomers
-
- 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
- C08F257/00—Macromolecular compounds obtained by polymerising monomers on to polymers of aromatic monomers as defined in group C08F12/00
- C08F257/02—Macromolecular compounds obtained by polymerising monomers on to polymers of aromatic monomers as defined in group C08F12/00 on to polymers of styrene or alkyl-substituted styrenes
-
- 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
- C08F279/00—Macromolecular compounds obtained by polymerising monomers on to polymers of monomers having two or more carbon-to-carbon double bonds as defined in group C08F36/00
- C08F279/02—Macromolecular compounds obtained by polymerising monomers on to polymers of monomers having two or more carbon-to-carbon double bonds as defined in group C08F36/00 on to polymers of conjugated dienes
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L51/00—Compositions of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers
- C08L51/04—Compositions of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers grafted on to rubbers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L55/00—Compositions of homopolymers or copolymers, obtained by polymerisation reactions only involving carbon-to-carbon unsaturated bonds, not provided for in groups C08L23/00 - C08L53/00
- C08L55/02—ABS [Acrylonitrile-Butadiene-Styrene] polymers
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- 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)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Polyurethanes Or Polyureas (AREA)
Abstract
Description
[BR]n−PUR
[式中、
BR=ジエンポリマー、ビニル芳香族−ジエンコポリマー、
PUR=主ポリウレタン単位、かつ
nは、2以上、好ましくは2〜10である]
を提供する。本発明では、使用する主ポリウレタン単位は、好ましくは多官能性イソシアナートおよび/またはチオイソシアナート(成分A)と多官能性プロトン酸(H-acid)化合物(成分B)から構成される生成物混合物を含む。
Q[NCX]q
[式中、
q=2以上の数、
X=OまたはS、好ましくはO、かつ
Qは、4〜1000個の炭素原子、好ましくは6〜500個の炭素原子を有するオリゴマー構造であり、この構造は二重結合を含むことができ、あるいはQは、2〜200個の炭素原子、好ましくは6〜100個の炭素原子を有する脂肪族炭化水素基、4〜200個の炭素原子、好ましくは5〜10個の炭素原子を有する脂環式炭化水素基、6〜200個の炭素原子、好ましくは6〜13個の炭素原子を有する芳香族炭化水素基、または8〜200個の炭素原子、好ましくは8〜12個の炭素原子を有するアリール脂肪族炭化水素基であり、適切な場合、記載したオリゴマー、脂肪族炭化水素基、脂環式炭化水素基、芳香族炭化水素基、およびアリール脂肪族炭化水素基は、O、N、Sの群から1個または複数のヘテロ原子を含む]。
T[YH]p、
[式中、
p=2以上の数
Y=O、S、またはNRであり、ここでRは、水素、2〜200個の炭素原子、好ましくは3〜10個の炭素原子を有する脂肪族炭化水素基、4〜200個の炭素原子、好ましくは5〜10個の炭素原子を有する脂環式炭化水素基、6〜200個の炭素原子、好ましくは6〜13個の炭素原子を有する芳香族炭化水素基、または8〜200個の炭素原子、好ましくは8〜12個の炭素原子を有するアリール脂肪族炭化水素基であり、適切な場合、記載した脂肪族炭化水素基、脂環式炭化水素基、芳香族炭化水素基、およびアリール脂肪族炭化水素基はそれぞれ、O、N、Sの群から1個または複数のヘテロ原子を含む]。
窒素中、乾燥した20Lの鋼製反応器に入っているテクニカルグレードのヘキサン中13重量%の1,3−ブタジエン溶液に、撹拌しながらジイソブチルアルミニウムヒドリドのヘキサン溶液(DIBAH;Al(C4H9)2H)、ネオジムバーサタート(neodymium versatate)に対して等モル量のエチルアルミニウムセスキクロリドのヘキサン溶液(EASC、Al2(C2H5)3Cl3)、およびネオジムバーサタートのヘキサン溶液(NdV、Nd(O2C10H19)3)を添加した。次いで、混合物を供給前温度の73℃に加熱する。反応は、反応の開始後60分で完結し、ポリマー標本を採取する。次いで、撹拌しながら、HDI(成分(A))を100mlのヘキサンと一緒にビュレットで添加する。さらに30分後、撹拌しながら、エチレングリコール(成分(B))をPUR触媒ラウリン酸ジブチルスズおよび100mlのヘキサンと一緒にビュレットで添加する。反応時間が1時間経過した後、100mlのヘキサンに溶解した2.6gの安定化剤Irganox 1520で、ポリマー溶液を安定化し、次いでポリマーを約10lのエタノールで沈澱させ、真空乾燥キャビネット中、60℃で乾燥する。
以下の物質を使用して、混合物を検討した。
Claims (8)
- 下記の式(I)による、共役ジエン、または共役ジエンおよびビニル芳香族化合物をベースとした変性ポリマー:
[BR]n−PUR
[式中、
BR=ジエンポリマー、ビニル芳香族−ジエンコポリマー、
PUR=主ポリウレタン単位、かつ
nは、2以上である]。 - 使用する主ポリウレタン単位が、多官能性イソシアナートおよび/またはチオイソシアナートと多官能性プロトン酸化合物から構成される生成物混合物を含むことを特徴とする、請求項1に記載の変性ポリマー。
- 使用するプロトン酸化合物が、チオール、アルコール、および/またはアミンを含むことを特徴とする、請求項1または2に記載の変性ポリマー。
- 使用する多官能性イソシアナートが、ヘキサメチレン1,6−ジイソシアナート、ジシクロヘキシルメタン4,4’−ジイソシアナート、トルエン2,4−および2,6−ジイソシアナート、ジフェニルメタン−2,4’−ジイソシアナート、および/またはジフェニルメタン4,4’−ジイソシアナートを含むことを特徴とする、請求項1〜3のいずれか一項に記載の変性ポリマー。
- 使用するジエンポリマーが、以下のモノマー:1,3−ブタジエン、2,3−ジメチル−1,3−ブタジエン、3−ブチル−1,3−オクタジエン、イソプレン、ピペリレン、1,3−ヘキサジエン、1,3−オクタジエン、2−フェニル−1,3−ブタジエンから調製された化合物を含むことを特徴とする、請求項1〜4のいずれか一項に記載の変性ポリマー。
- BR対PURの重量比が、少なくとも100g:0.01g〜30gであることを特徴とする、請求項1〜5のいずれか一項に記載の変性ポリマー。
- 共役ジエンを含む化合物を、まず単独でまたはビニル芳香族化合物と一緒に重合し、次いでこれらのポリマーを多官能性イソシアナートおよび/またはチオイソシアナートの化合物と反応させ、次いでこの得られたポリマー溶液を多官能性プロトン酸化合物と反応させることを特徴とする、請求項1〜6のいずれか一項に記載の変性ポリマーの調製方法。
- タイヤおよびタイヤ構成要素、またはHIPSプラスチックおよびABSプラスチック、ならびにゴルフボールを生成するための請求項1〜6のいずれか一項に記載の変性ポリマーの使用。
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PCT/EP2008/060447 WO2009021917A1 (de) | 2007-08-16 | 2008-08-08 | Modifizierte polymere auf basis von konjugierten dienen oder von konjugierten dienen und vinylaromatischen verbindungen, ein verfahren zu deren herstellung sowie deren verwendung |
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2008
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- 2008-08-08 WO PCT/EP2008/060447 patent/WO2009021917A1/de active Application Filing
- 2008-08-08 CN CN2008801069276A patent/CN101802041B/zh not_active Expired - Fee Related
- 2008-08-08 KR KR1020107005706A patent/KR101259231B1/ko active IP Right Grant
- 2008-08-08 JP JP2010520544A patent/JP2010536946A/ja active Pending
- 2008-08-08 RU RU2010109440/04A patent/RU2446182C2/ru active
- 2008-08-08 EP EP08787042A patent/EP2181134A1/de not_active Withdrawn
- 2008-08-08 BR BRPI0815390-6A2A patent/BRPI0815390A2/pt not_active Application Discontinuation
- 2008-08-15 TW TW097131055A patent/TWI422606B/zh not_active IP Right Cessation
- 2008-08-16 SA SA08290507A patent/SA08290507B1/ar unknown
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2010
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Cited By (5)
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JP2014506277A (ja) * | 2010-12-23 | 2014-03-13 | コンパニー ゼネラール デ エタブリッスマン ミシュラン | トレッドが熱可塑性ポリウレタンブロックコポリマーを含むタイヤ |
JP2019518130A (ja) * | 2016-05-24 | 2019-06-27 | 北京化工大学Beijing University Of Chemical Technology | 高性能タイヤ用溶液重合スチレン−ブタジエンゴム−ポリウレタンエラストマー材料及び製造方法 |
US10717854B2 (en) | 2016-05-24 | 2020-07-21 | Beijing University of Chemical Tehcnology | Solution polymerized styrene-butadiene rubber-polyurethane elastomer material for high performance tire and preparation method thereof |
JPWO2021054254A1 (ja) * | 2019-09-20 | 2021-03-25 | ||
WO2021054254A1 (ja) * | 2019-09-20 | 2021-03-25 | 株式会社ブリヂストン | ゴム組成物及びそれを用いたタイヤ |
Also Published As
Publication number | Publication date |
---|---|
KR20100054832A (ko) | 2010-05-25 |
BRPI0815390A2 (pt) | 2015-02-10 |
CN101802041B (zh) | 2013-11-06 |
WO2009021917A1 (de) | 2009-02-19 |
TWI422606B (zh) | 2014-01-11 |
KR101259231B1 (ko) | 2013-04-30 |
TW200920757A (en) | 2009-05-16 |
RU2446182C2 (ru) | 2012-03-27 |
SA08290507B1 (ar) | 2012-06-23 |
RU2010109440A (ru) | 2011-09-27 |
EP2181134A1 (de) | 2010-05-05 |
DE102007038442A1 (de) | 2009-02-19 |
CN101802041A (zh) | 2010-08-11 |
ZA201001080B (en) | 2011-04-28 |
US20110251348A1 (en) | 2011-10-13 |
JP2014198855A (ja) | 2014-10-23 |
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