JP6263526B2 - 官能化および分枝化されたエラストマー性コポリマーの調製方法 - Google Patents
官能化および分枝化されたエラストマー性コポリマーの調製方法 Download PDFInfo
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- JP6263526B2 JP6263526B2 JP2015516719A JP2015516719A JP6263526B2 JP 6263526 B2 JP6263526 B2 JP 6263526B2 JP 2015516719 A JP2015516719 A JP 2015516719A JP 2015516719 A JP2015516719 A JP 2015516719A JP 6263526 B2 JP6263526 B2 JP 6263526B2
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- Prior art keywords
- lithium
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- conjugated diene
- elastomeric
- diene monomer
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- 229910052744 lithium Inorganic materials 0.000 claims description 31
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- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 28
- -1 bromine compound Chemical class 0.000 claims description 28
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- VXEGSRKPIUDPQT-UHFFFAOYSA-N 4-[4-(4-methoxyphenyl)piperazin-1-yl]aniline Chemical compound C1=CC(OC)=CC=C1N1CCN(C=2C=CC(N)=CC=2)CC1 VXEGSRKPIUDPQT-UHFFFAOYSA-N 0.000 description 3
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- WITDFSFZHZYQHB-UHFFFAOYSA-N dibenzylcarbamothioylsulfanyl n,n-dibenzylcarbamodithioate Chemical compound C=1C=CC=CC=1CN(CC=1C=CC=CC=1)C(=S)SSC(=S)N(CC=1C=CC=CC=1)CC1=CC=CC=C1 WITDFSFZHZYQHB-UHFFFAOYSA-N 0.000 description 3
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- HXOGQBSDPSMHJK-UHFFFAOYSA-N triethoxy(6-methylheptyl)silane Chemical compound CCO[Si](OCC)(OCC)CCCCCC(C)C HXOGQBSDPSMHJK-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- 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
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Description
(a)少なくとも1つの炭化水素溶剤と、少なくとも1つのリチウム系開始剤と、少なくとも1つの極性調整剤の存在下で、少なくとも1つの共役ジエンモノマーと少なくとも1つのビニルアレーンをアニオン共重合させて、エラストマー性コポリマーを含む溶液を得るステップ。
(b)ステップ(a)で得たエラストマー性コポリマー中に存在するポリマー鎖の少なくとも10重量%、好ましくは20重量%〜100重量%を、エポキシド、ケトン、エステル、アルデヒドから選択された少なくとも1つの官能基を有する少なくとも1つの化合物と反応させて、官能化エラストマー性コポリマーを含む溶液を得るステップ。
(c)ステップ(b)で得た溶液に、ステップ(a)で用いたリチウム系開始剤のモル量の1〜4倍、好ましくは1.5〜3倍の量のリチウム系開始剤と、一般式(I):
R‐Br (I)
(式中、Rは直鎖または分枝C1〜C30アルキル基、好ましくはC2〜C10アルキル基;C3〜C30シクロアルキル基、好ましくはC4〜C10シクロアルキル基;C6〜C30アリール基、好ましくはC6〜C12アリール基を表わす)を有する臭素化合物を添加するステップ。
共役ジエンモノマーとビニルアレーンの合計重量の60重量%〜95重量%、好ましくは70重量%〜90重量%の少なくとも1つの共役ジエンモノマーと、
共役ジエンモノマーとビニルアレーンの合計重量の5重量%〜40重量%、好ましくは10重量%〜30重量%の少なくとも1つのビニルアレーン、の存在下で行うことができる。
R’(Li)n (II)
(式中、R’は直鎖または分枝C1〜C20アルキル基、好ましくはC2〜C8アルキル基;nは1〜4の範囲の整数を表わす)を有する化合物から選択することができる。
ミクロ構造(1,2‐ビニル単位と結合スチレンの含有量)の測定は、1,4‐シス(800cm−1と640cm−1)、1,4‐トランス(1018cm−1と937cm−1)、1,2(934cm−1と887cm−1)の3種類のブタジエン連鎖および結合スチレン(715cm−1から680cm−1)に特有の吸収帯(およびそれらの相対強度の算出)によるフーリエ変換赤外(FTIR:Fourier Transform Infra Red)分光法を用いて行った。
分子質量分布(MWD)の測定は、種々の大きさの細孔を有する架橋ポリスチレンからなる固相を含む一連のカラムに、得られたコポリマーのテトラヒドロフラン(THF)溶液を通過させることにより行われるゲル浸透クロマトグラフィ(GPC:gel permeation chromatography)を用いて得た。
ムーニー粘度の測定は、ロータはL型、時間は1+4を用いるASTM D1646法にしたがって、モンサント(Monsanto)社のMV2000E粘度計を用いて100℃で行った(ML1+4@100℃)。
ガラス転移温度(Tg)の測定は、示差走査熱量測定(DSC:Differential Scanner Calorimetry)によって行った。
・周波数:10Hz
・温度:0℃と60℃
・歪み範囲:0.1%÷10%
・形状:長方形ねじり
・温度範囲:−130℃÷100℃@2℃/分
・周波数:1Hz
・歪み:0.1%
・形状:長方形ねじり
・冷却:3℃/分
充填率80%と同等である重量比9/1のシクロヘキサン/n‐ヘキサンの無水混合物8000g、開始剤の理論量とのモル比がおおよそ3:1の350ppmに相当する極性調整剤(テトラヒドロフルフリルエチルエーテル(THFAエチル))3.22g、続いて、スチレン300gと1,3‐ブタジエン900gを16リットル攪拌リアクタに投入した。得られた反応混合物を加熱ジャケットによって40℃に加熱した。次いで、n‐ヘキサン中のリチウムn‐ブチル0.48g(15重量%の溶液では3.2g)を添加した。次いで、ジャケットの加熱を遮断したが、反応の発熱性の結果として、反応物の温度上昇が得られ、最終温度(ピーク温度)は約78℃まで上昇した。ピーク温度に達した後10分間放置して遊離モノマーの転化を完了させ、次いで理論上のカップリング効率50%に相当する四塩化ケイ素0.159gを加えた。5分後、塩化トリメチルシラン0.405gを加えて、残りのリビング鎖末端を非活性化した。10分後、得られた溶液をタンクに排出し、そこで2,6‐ジ‐t‐ブチルフェノール(BHT)0.7phrを用いて固定化させた。そして混合物全体を脱溶媒化部へ送り、水を用いてストリッピングを行った。
充填率80%と同等である重量比9/1のシクロヘキサン/n‐ヘキサンの無水混合物8000g、開始剤の理論量とのモル比がおおよそ3:1の350ppmに相当する極性調整剤(テトラヒドロフルフリルエチルエーテル(THFAエチル))3.22g、続いて、スチレン300gと1,3‐ブタジエン900gを16リットル攪拌リアクタに投入した。得られた反応混合物を加熱ジャケットによって40℃に加熱した。次いで、n‐ヘキサン中のリチウムn‐ブチル0.48g(15重量%の溶液では3.2g)を添加した。次いで、ジャケットの加熱を遮断したが、反応の発熱性の結果として、反応生成量の温度上昇が得られ、最終温度(ピーク温度)は約78℃まで上昇した。ピーク温度に達した後10分間放置して遊離モノマーの転化を完了させ、次いで、既に得ている線状ポリマーにランダムな分枝を導入するために、1‐ブロモ‐オクタン2.784gとともにリチウムn‐ブチル0.84g(15重量%溶液では5.6g)を加えた。10分後、得られた溶液をタンクに排出し、そこで2,6‐ジ‐t‐ブチルフェノール(BHT)0.7phrを用いて固定化させた。そして混合物全体を脱溶媒化部へ送り、水を用いてストリッピングを行った。
充填率80%と同等である重量比9/1のシクロヘキサン/n‐ヘキサンの無水混合物8000g、開始剤の理論量とのモル比がおおよそ3:1の350ppmに相当する極性調整剤(テトラヒドロフルフリルエチルエーテル(THFAエチル))3.22g、続いて、スチレン300gと1,3‐ブタジエン900gを16リットル攪拌リアクタに投入した。得られた反応混合物を加熱ジャケットによって40℃に加熱した。次いで、n‐ヘキサン中のリチウムn‐ブチル0.48g(15重量%の溶液では3.2g)を添加した。次いで、ジャケットの加熱を遮断したが、反応の発熱性の結果として、反応生成量の温度上昇が得られ、最終温度(ピーク温度)は約78℃まで上昇した。ピーク温度に達した後10分間放置して遊離モノマーの転化を完了させ、次いで理論上のカップリング効率35%に相当する四塩化ケイ素0.111gを添加した。5分後、1,4‐シクロヘキサンジメタノールジグリシジルエーテル0.42gを加えてリビング鎖末端と反応させ、該鎖末端を官能化させた。10分後、得られた溶液をタンクに排出し、そこで2,6‐ジ‐t‐ブチルフェノール(BHT)0.7phrを用いて固定化させた。そして混合物全体を脱溶媒化部へ送り、水を用いてストリッピングを行った。
充填率80%と同等である重量比9/1のシクロヘキサン/n‐ヘキサンの無水混合物8000g、開始剤の理論量とのモル比がおおよそ3:1の350ppmに相当する極性調整剤(テトラヒドロフルフリルエチルエーテル(THFAエチル))3.22g、続いて、スチレン300gと1,3‐ブタジエン900gを16リットル攪拌リアクタに投入した。得られた反応混合物を加熱ジャケットによって40℃に加熱した。次いで、n‐ヘキサン中のリチウムn‐ブチル0.48g(15重量%の溶液では3.2g)を添加した。次いで、ジャケットの加熱を遮断したが、反応の発熱性の結果として、反応生成量の温度上昇が得られ、最終温度(ピーク温度)は約78℃まで上昇した。ピーク温度に達した後10分間放置して遊離モノマーの転化を完了させ、次いで、同じ化合物のエポキシ基とポリマーの反応性カルバニオンの鎖末端の間の化学量論的反応に相当する、1,4‐シクロヘキサンジメタノールジグリシジルエーテルを0.84g加えた。5分後、既に得た線状ポリマーにランダムな分枝を導入するために、1‐ブロモ‐オクタン2.784gとともにリチウムn‐ブチル0.84g(15重量%溶液では5.6g)を加えた。10分後、得られた溶液をタンクに排出し、そこで2,6‐ジ‐t‐ブチルフェノール(BHT)0.7phrを用いて固定化させた。そして混合物全体を脱溶媒化部へ送り、水を用いてストリッピングを行った。
エラストマー性組成物の調製
表2に記載した配合にしたがって、1.6リットルのバンバリー(Banbury)型密閉式ミキサ内でエラストマー性組成物を調製した。
・初期温度:50℃
・サイクル1/2/3:6分+5分+2分
・最終温度:100℃
BR:シス‐1,4‐ポリブタジエン(Europrene(登録商標)Neocis BR40、Polimeri Europa(現versalis spa)社製)
シリカ:Ultrasil(登録商標)7000、Evonik社製
N234:カーボンブラック
シラン:ビス(トリエトキシシリルプロピル)ポリスルフィド(Si 75(登録商標)、Evonik社製)
Vivatec(登録商標)500:芳香族系オイル(TDAE:Treated Distillated Aromatic Extract、BP社製)
6−PPD(酸化防止剤):N‐(1,3‐ジメチルブチル‐N’‐フェニル‐p‐フェニレンジアミン(Santoflex(登録商標)13、Monsanto社製)
パラフィンワックス:Riowax(登録商標)721、Andrea Gallo Di Luigi s.r.l.社製
DPG(促進剤):ジフェニルグアニジン(Rhenogran(登録商標)DPG80、Rhein Chemie社製)
CBS(促進剤):N‐シクロヘキシル‐2‐ベンゾチアジル‐スルフェンアミド(Vulkacit(登録商標)CZ、Bayer社製)
TBzTD(促進剤):N,N,N’,N’‐テトラベンジルチウラムジスルフィド(IsoQure(登録商標)TBzTD、Kautshuck Gesellschaft Group社製)
Claims (18)
- 官能化および分枝化されたエラストマー性コポリマーの調製方法であって、
(a)少なくとも1つの炭化水素溶剤と、少なくとも1つのリチウム系開始剤と、少なくとも1つの極性調整剤の存在下で、少なくとも1つの共役ジエンモノマーと少なくとも1つのビニルアレーンをアニオン共重合させて、エラストマー性コポリマーを含む溶液を得るステップと、
(b)ステップ(a)で得たエラストマー性コポリマーに存在するポリマー鎖の少なくとも10重量%を、エポキシド、ケトン、エステル、アルデヒドから選択される少なくとも1つの官能基を有する少なくとも1つの化合物と反応させて、官能化エラストマー性コポリマーを含む溶液を得るステップと、
(c)ステップ(b)で得た溶液に、ステップ(a)で用いたリチウム系開始剤のモル量の1〜4倍の量のリチウム系開始剤と、一般式(I):
R−Br (I)
(式中、Rは直鎖または分枝C1〜C30アルキル基、C3〜C30シクロアルキル基、C6〜C30アリール基を表わす)を有する臭素化合物を添加するステップと、を含む方法。 - 請求項1に記載の方法であって、ステップ(b)において、ステップ(a)で得られたエラストマー性コポリマーに存在するポリマー鎖の20重量%〜100重量%を反応させる、方法。
- 請求項1または2に記載の方法であって、前記共役ジエンモノマーは、1,3‐ブタジエン、イソプレン、2,3‐ジメチル‐1,3‐ブタジエン、1,3‐ペンタジエン(ピペリレン)、2‐メチル‐3‐エチル‐1,3‐ブタジエン、1,3‐オクタジエン、またはそれらの混合物から選択される、方法。
- 請求項1〜3のいずれか一項に記載の方法であって、前記ビニルアレーンは、スチレン、α‐メチルスチレン、1‐ビニル‐ナフタレン、2‐ビニル‐ナフタレン、またはそれらのアルキル誘導体、またはそれらの混合物から選択される、方法。
- 請求項1〜4のいずれか一項に記載の方法であって、前記アニオン共重合は、
前記共役ジエンモノマーと前記ビニルアレーンの合計重量に対して60重量%〜95重量%の少なくとも1つの共役ジエンモノマーと、
前記共役ジエンモノマーと前記ビニルアレーンの合計重量に対して5重量%〜40重量%の少なくとも1つのビニルアレーンの存在下で行われる、方法。 - 請求項1〜5のいずれか一項に記載の方法であって、前記炭化水素溶剤は、n‐ペンタン、n‐ヘキサン、n‐ヘプタン、シクロヘキサン、またはそれらの混合物といった脂肪族炭化水素溶剤または芳香族炭化水素溶剤から選択される、方法。
- 請求項1〜6のいずれか一項に記載の方法であって、前記リチウム系開始剤は、一般式(II)
R’(Li)n (II)
(式中、R’は直鎖または分枝C1〜C20アルキル基、nは1〜4の範囲の整数を表わす)を有する化合物から選択される、方法。 - 請求項1〜7のいずれか一項に記載の方法であって、前記リチウム系開始剤の使用量は、前記モノマー(すなわち、共役ジエンモノマーとビニルアレーン)の合計重量に対して、0.005重量%〜0.08重量%の範囲である、方法。
- 請求項1〜8のいずれか一項に記載の方法であって、前記極性調整剤は、テトラヒドロフラン(THF)、テトラヒドロフルフリルエチルエーテル(THFAエチル)、またはそれらの混合物といったエーテル;N,N,N’,N’‐テトラメチルエチレンジアミン(TMEDA)、またはそれらの混合物といったジアミン;またはそれらの混合物から選択される、方法。
- 請求項1〜9のいずれか一項に記載の方法であって、前記極性調整剤の使用量は、前記リチウム系開始剤1モル当たり、0.10モル〜100モルの範囲である、方法。
- 請求項1〜10のいずれか一項に記載の方法であって、前記ステップ(a)が行われる温度は、0℃から150℃の範囲である、方法。
- 請求項1〜11のいずれか一項に記載の方法であって、前記ステップ(a)が行われる時間は、5分から10時間の範囲である、方法。
- 請求項1〜12のいずれか一項に記載の方法であって、前記少なくとも1つの官能基を有する化合物はエポキシドから選択される、方法。
- 請求項1〜13のいずれか一項に記載の方法であって、前記ステップ(b)が行われる温度は、0℃から150℃の範囲である、方法。
- 請求項1〜14のいずれか一項に記載の方法であって、前記ステップ(b)が行われる時間は、1分から1時間の範囲である、方法。
- 請求項1〜15のいずれか一項に記載の方法であって、前記一般式(I)を有する臭素化合物の使用量は、該一般式(I)を有する臭素化合物と前記各リチウム系開始剤の合計(ステップ(a)のリチウム系開始剤+ステップ(c)のリチウム系開始剤)とのモル比が、0.6:1〜1:1の範囲となるような量である、方法。
- 請求項1〜16のいずれか一項に記載の方法であって、前記ステップ(c)が行われる温度は、0℃から150℃の範囲である、方法。
- 請求項1〜17のいずれか一項に記載の方法であって、前記ステップ(c)が行われる時間は、1分から1時間の範囲である、方法。
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ITMI20070626A1 (it) * | 2007-03-29 | 2008-09-30 | Polimeri Europa Spa | Mescola vulcanizzabile comprendente copolineri ramificati vinilarene-diene coniugato parzialmente idrogenati |
IT1391109B1 (it) * | 2008-08-20 | 2011-11-18 | Polimeri Europa Spa | Procedimento per la sintesi di poli(1,3-alcadieni) funzionalizzati e loro impiego nella preparazione di polimeri vinilaromatici ad alta resistenza all'urto |
EP2342240B1 (en) * | 2008-10-14 | 2014-02-12 | Bridgestone Corporation | New polymers and use thereof in preparation of high impact polymeric compositions |
KR101187270B1 (ko) * | 2010-01-21 | 2012-10-04 | 주식회사 엘지화학 | 용액 중합 폴리스티렌-부타디엔 고무 및 이의 제조방법 |
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2013
- 2013-06-10 PL PL13744812.2T patent/PL2859022T3/pl unknown
- 2013-06-10 WO PCT/IB2013/054746 patent/WO2013186691A1/en active Application Filing
- 2013-06-10 BR BR112014029438-0A patent/BR112014029438B1/pt active IP Right Grant
- 2013-06-10 JP JP2015516719A patent/JP6263526B2/ja active Active
- 2013-06-10 KR KR1020147034383A patent/KR101961909B1/ko active IP Right Grant
- 2013-06-10 US US14/404,703 patent/US9534071B2/en active Active
- 2013-06-10 RU RU2014145811A patent/RU2621672C2/ru active
- 2013-06-10 CN CN201380031134.3A patent/CN104395353B/zh active Active
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Also Published As
Publication number | Publication date |
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PL2859022T3 (pl) | 2016-10-31 |
KR20150022813A (ko) | 2015-03-04 |
RU2621672C2 (ru) | 2017-06-07 |
US20150183913A1 (en) | 2015-07-02 |
RU2014145811A (ru) | 2016-07-27 |
JP2015523432A (ja) | 2015-08-13 |
ITMI20121018A1 (it) | 2013-12-13 |
EP2859022A1 (en) | 2015-04-15 |
CN104395353A (zh) | 2015-03-04 |
BR112014029438B1 (pt) | 2020-12-15 |
KR101961909B1 (ko) | 2019-03-25 |
MX2014013987A (es) | 2015-06-04 |
ZA201408288B (en) | 2016-08-31 |
EP2859022B1 (en) | 2016-04-13 |
BR112014029438A2 (pt) | 2017-06-27 |
CN104395353B (zh) | 2016-06-08 |
US9534071B2 (en) | 2017-01-03 |
WO2013186691A1 (en) | 2013-12-19 |
MX341225B (es) | 2016-08-11 |
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