JP2019108448A - タイヤ用ゴム組成物及び空気入りタイヤ - Google Patents
タイヤ用ゴム組成物及び空気入りタイヤ Download PDFInfo
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- JP2019108448A JP2019108448A JP2017241693A JP2017241693A JP2019108448A JP 2019108448 A JP2019108448 A JP 2019108448A JP 2017241693 A JP2017241693 A JP 2017241693A JP 2017241693 A JP2017241693 A JP 2017241693A JP 2019108448 A JP2019108448 A JP 2019108448A
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- rubber
- copolymer
- conjugated diene
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- 239000005060 rubber Substances 0.000 title claims abstract description 129
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims abstract description 77
- 150000001993 dienes Chemical group 0.000 claims abstract description 75
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- 239000006229 carbon black Substances 0.000 claims abstract description 46
- 239000000377 silicon dioxide Substances 0.000 claims abstract description 38
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 34
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- 125000005370 alkoxysilyl group Chemical group 0.000 description 16
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 16
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- 125000003118 aryl group Chemical group 0.000 description 14
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- 239000011572 manganese Substances 0.000 description 13
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- 238000012545 processing Methods 0.000 description 12
- CSRZQMIRAZTJOY-UHFFFAOYSA-N trimethylsilyl iodide Chemical compound C[Si](C)(C)I CSRZQMIRAZTJOY-UHFFFAOYSA-N 0.000 description 12
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- RXJKFRMDXUJTEX-UHFFFAOYSA-N triethylphosphine Chemical compound CCP(CC)CC RXJKFRMDXUJTEX-UHFFFAOYSA-N 0.000 description 1
- ORYGRKHDLWYTKX-UHFFFAOYSA-N trihexylalumane Chemical compound CCCCCC[Al](CCCCCC)CCCCCC ORYGRKHDLWYTKX-UHFFFAOYSA-N 0.000 description 1
- GCZKMPJFYKFENV-UHFFFAOYSA-K triiodogold Chemical compound I[Au](I)I GCZKMPJFYKFENV-UHFFFAOYSA-K 0.000 description 1
- ZNXDCSVNCSSUNB-UHFFFAOYSA-N trimethoxy-[2-(oxiran-2-ylmethoxy)ethyl]silane Chemical compound CO[Si](OC)(OC)CCOCC1CO1 ZNXDCSVNCSSUNB-UHFFFAOYSA-N 0.000 description 1
- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 0.000 description 1
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 1
- LFXVBWRMVZPLFK-UHFFFAOYSA-N trioctylalumane Chemical compound CCCCCCCC[Al](CCCCCCCC)CCCCCCCC LFXVBWRMVZPLFK-UHFFFAOYSA-N 0.000 description 1
- JOJQVUCWSDRWJE-UHFFFAOYSA-N tripentylalumane Chemical compound CCCCC[Al](CCCCC)CCCCC JOJQVUCWSDRWJE-UHFFFAOYSA-N 0.000 description 1
- CNWZYDSEVLFSMS-UHFFFAOYSA-N tripropylalumane Chemical compound CCC[Al](CCC)CCC CNWZYDSEVLFSMS-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- MDDPTCUZZASZIQ-UHFFFAOYSA-N tris[(2-methylpropan-2-yl)oxy]alumane Chemical compound [Al+3].CC(C)(C)[O-].CC(C)(C)[O-].CC(C)(C)[O-] MDDPTCUZZASZIQ-UHFFFAOYSA-N 0.000 description 1
- 125000004417 unsaturated alkyl group Chemical group 0.000 description 1
- 238000011144 upstream manufacturing Methods 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000010456 wollastonite Substances 0.000 description 1
- 229910052882 wollastonite Inorganic materials 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
- 239000007218 ym medium Substances 0.000 description 1
- 239000007222 ypd medium Substances 0.000 description 1
- 150000003752 zinc compounds Chemical class 0.000 description 1
- UGZADUVQMDAIAO-UHFFFAOYSA-L zinc hydroxide Chemical compound [OH-].[OH-].[Zn+2] UGZADUVQMDAIAO-UHFFFAOYSA-L 0.000 description 1
- 229940007718 zinc hydroxide Drugs 0.000 description 1
- 229910021511 zinc hydroxide Inorganic materials 0.000 description 1
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 description 1
- 229910000368 zinc sulfate Inorganic materials 0.000 description 1
- 229960001763 zinc sulfate Drugs 0.000 description 1
- ZUBNXRHITOZMOO-UHFFFAOYSA-N zinc;octadecanoic acid;oxygen(2-) Chemical compound [O-2].[Zn+2].CCCCCCCCCCCCCCCCCC(O)=O ZUBNXRHITOZMOO-UHFFFAOYSA-N 0.000 description 1
- 150000007934 α,β-unsaturated carboxylic acids Chemical class 0.000 description 1
- IHPKGUQCSIINRJ-UHFFFAOYSA-N β-ocimene Natural products CC(C)=CCC=C(C)C=C IHPKGUQCSIINRJ-UHFFFAOYSA-N 0.000 description 1
Classifications
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- 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
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- C08F136/00—Homopolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds
- C08F136/02—Homopolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds
- C08F136/04—Homopolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds conjugated
- C08F136/06—Butadiene
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F236/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds
- C08F236/02—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds
- C08F236/04—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds conjugated
- C08F236/10—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds conjugated with vinyl-aromatic monomers
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- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
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Abstract
Description
(a)成分:ランタノイドからなる群より選択される少なくとも1種の元素を含有するランタノイド含有化合物、又は、該ランタノイド含有化合物とルイス塩基との反応により得られる反応生成物
(b)成分:アルミノオキサン、及び、一般式(3−1);AlR31R32R33で表される有機アルミニウム化合物(ただし、一般式(3−1)中、R31及びR32は、同一又は異なって、炭素数1〜10の炭化水素基又は水素原子を表す。R33は、R31及びR32と同一又は異なって、炭素数1〜10の炭化水素基を表す。)からなる群より選択される少なくとも1種の化合物
(c)成分:その分子構造中に少なくとも1個のヨウ素原子を含有するヨウ素含有化合物
(a)成分:ランタノイドからなる群より選択される少なくとも1種の元素を含有するランタノイド含有化合物、又は、該ランタノイド含有化合物とルイス塩基との反応により得られる反応生成物
(b)成分:アルミノオキサン、及び、一般式(3−1);AlR31R32R33で表される有機アルミニウム化合物(ただし、一般式(3−1)中、R31及びR32は、同一又は異なって、炭素数1〜10の炭化水素基又は水素原子を表す。R33は、R31及びR32と同一又は異なって、炭素数1〜10の炭化水素基を表す。)からなる群より選択される少なくとも1種の化合物
(c)成分:その分子構造中に少なくとも1個のヨウ素原子を含有するヨウ素含有化合物
上記R36の具体例としては、メチル基、エチル基、プロピル基、ブチル基、イソブチル基、t−ブチル基、ヘキシル基、イソヘキシル基、オクチル基、イソオクチル基等が挙げられる。なかでも、メチル基、エチル基、イソブチル基、t−ブチル基が好ましく、メチル基が特に好ましい。
また、上記pは、4〜100の整数であることが好ましい。
また、上記ヨウ化炭化水素化合物(上記一般式(3−7)で示される化合物)の具体例としては、メチルアイオダイド、ブチルアイオダイド、ヘキシルアイオダイド、オクチルアイオダイド、ヨードホルム、ジヨードメタン、ベンジリデンアイオダイド等が挙げられる。なかでも、メチルアイオダイド、ヨードホルム、ジヨードメタンが好ましい。
なお、共役ジエン系重合体のムーニー粘度(ML1+4、100℃)は後述の実施例に記載の測定方法により得られる値である。
これら変性剤は、単独で用いてもよいし、2種以上を組み合わせて用いてもよい。また、上述のアルコキシシラン化合物の部分縮合物を用いることもできる。
これらの官能基導入剤は、単独で用いてもよいし、2種以上を組み合わせて用いてもよい。
なお、変性共役ジエン系重合体のムーニー粘度(ML1+4、125℃)は後述の実施例に記載の測定方法により得られる値である。
ここで、変性共役ジエン系重合体のガラス転移温度は、後述の実施例に記載の測定方法により測定することができる。
なお、イソプレン系ゴムの含有量は、変性イソプレン系ゴム及び非変性イソプレン系ゴムの合計含有量である。
なお、BRの含有量は、変性BR及び非変性BRの合計含有量である。
シリカとしては特に限定されず、例えば、乾式法シリカ(無水シリカ)、湿式法シリカ(含水シリカ)などがあげられるが、シラノール基が多いという理由から、湿式法シリカが好ましい。これらは単独で用いてもよく、2種以上を組み合わせて用いてもよい。
なお、シリカのN2SAは、ASTM D3037−93に準じてBET法で測定される値である。
シランカップリング剤としては、ゴム工業において、従来からシリカと併用される任意のシランカップリング剤を使用することができ、例えば、ビス(3−トリエトキシシリルプロピル)テトラスルフィド等のスルフィド系、3−メルカプトプロピルトリメトキシシランなどのメルカプト系、ビニルトリエトキシシランなどのビニル系、3−アミノプロピルトリエトキシシランなどのアミノ系、γ−グリシドキシプロピルトリエトキシシランのグリシドキシ系、3−ニトロプロピルトリメトキシシランなどのニトロ系、3−クロロプロピルトリメトキシシランなどのクロロ系等が挙げられる。なかでも、上記共重合体とともに配合することで、各性能の改善効果を相乗的に高めることができる点から、メルカプト系シランカップリング剤が好ましい。
上記式(2−1)におけるR109の例として、直鎖状アルキレン基としては、メチレン基、エチレン基、n−プロピレン基、n−ブチレン基、ヘキシレン基等が挙げられ、分枝状アルキレン基としては、イソプロピレン基、イソブチレン基、2−メチルプロピレン基等が挙げられる。
なお、結合単位A、Bの含有量は、結合単位A、Bがシランカップリング剤の末端に位置する場合も含む量である。結合単位A、Bがシランカップリング剤の末端に位置する場合の形態は特に限定されず、結合単位A、Bを示す式(2−2)、(2−3)と対応するユニットを形成していればよい。
SAF、ISAF、HAF、MAF、FEF、SRF、GPF、APF、FF、CF、SCF及びECFのようなファーネスブラック(ファーネスカーボンブラック);アセチレンブラック(アセチレンカーボンブラック);FT及びMTのようなサーマルブラック(サーマルカーボンブラック);EPC、MPC及びCCのようなチャンネルブラック(チャンネルカーボンブラック);グラファイトなどをあげることができる。これらは1種又は2種以上組み合わせて用いることができる。
なお、カーボンブラックの窒素吸着比表面積は、JIS K 6217−2:2001によって求められる。
なお、本明細書において、カーボンブラックのCOANは、JIS K6217−4の測定方法によって求められる。なお、使用したオイルはジブチルフタレート(フタル酸ジブチル)である。
なお、本明細書において、カーボンブラックの揮発分量は、JIS K6221(1994)に準拠した測定方法によって求められる。
R1及びR2の炭化水素基の炭素数は1〜11であり、好ましくは2〜9、より好ましくは4〜7である。
なお、本明細書において、単素環基とは、環構造が炭素原子のみによって構成される基を意味し、複素環基とは、環構造が炭素原子を含む2種類以上の元素によって構成される基を意味する。
アルキル基としては、例えば、メチル基、エチル基、n−プロピル基、イソプロピル基、n−ブチル基、sec−ブチル基、tert−ブチル基等が挙げられる。
R3としては、アルキル基が好ましい。
上記一般式(1)で表されるテトラジン系化合物は、市販品を用いてもよく、公知の方法により合成してもよい。
[式(1−2)中、R12は、窒素原子、酸素原子、硫黄原子、フッ素原子およびケイ素原子からなる群より選択される少なくとも1種の原子を含む官能基を示す。また、R12は塩を形成してもよい。]
[式(1−3)中、R13及びR14は同一でも異なっていても良く、各々水素原子(−H)又はアルキル基を示す。また、R13及びR14は塩を形成してもよい。]
[式(1−4)中、R15及びR16は同一でも異なっていても良く、各々水素原子(−H)、−COOR18(R18は水素原子(−H)又はアルキル基を示す)、又は窒素原子、酸素原子、硫黄原子、フッ素原子およびケイ素原子からなる群より選択される少なくとも1種の原子を含む官能基を示す。また、R15及びR16は塩を形成してもよい。]
R11の炭化水素基の炭素数はR1及びR2の炭化水素基と同様であり、好適な態様も同様である。
R17としては、アルキル基が好ましい。
R18としては、アルキル基が好ましい。
ここで、本明細書において、上記一般式(1)で表されるテトラジン系化合物の含有量とは、2種以上のテトラジン系化合物を含有する場合はその合計含有量を意味する。
可塑剤とは、ゴム成分に可塑性を付与する材料であり、例えば、オイル、レジン等が挙げられる。これらは単独で用いてもよく、2種以上を併用してもよい。。なかでも、オイル、レジンが好ましく、上記共重合体とともに配合することで、各性能の改善効果を相乗的に高めることができる点から、レジンがより好ましい。
なお、本明細書において、樹脂の軟化点は、JIS K 6220−1:2001に規定される軟化点を環球式軟化点測定装置で測定し、球が降下した温度である。
同様の理由から、ファルネセン−スチレン共重合体のTgは、好ましくは−15℃以下、より好ましくは−30℃以下であり、好ましくは−80℃以上、より好ましくは−70℃以上である。
同様の理由から、ファルネセン−ブタジエン共重合体のTgは、好ましくは−60℃以下、より好ましくは−70℃以下であり、好ましくは−120℃以上、より好ましくは−110℃以上である。
なお、本明細書において、ファルネセン系樹脂のTgは、JIS−K7121:1987に従い、ティー・エイ・インスツルメント・ジャパン社製の示差走査熱量計(Q200)を用いて、昇温速度10℃/分の条件で測定した値である。
また、ファルネセン−ビニルモノマー共重合体のMwは、好ましくは3000以上、より好ましくは5000以上、更に好ましくは8000以上である。3000以上であると、操縦安定性能が向上する傾向がある。また、該Mwは、好ましくは500000以下、より好ましくは300000以下、更に好ましくは150000以下、特に好ましくは100000以下である。500000以下であると、ウェットグリップ性能が向上する傾向がある。
Mwが上記範囲内のファルネセン単独重合体、ファルネセン−ビニルモノマー共重合体は、常温で液状であり、タイヤ用軟化剤として好適に使用できる。
同様の理由から、ファルネセン−ビニルモノマー共重合体の溶融粘度は、好ましくは1000Pa・s以下、より好ましくは650Pa・s以下、更に好ましくは200Pa・s以下であり、好ましくは1Pa・s以上、より好ましくは5Pa・s以上である。
なお、本明細書において、ファルネセン系樹脂の溶融粘度は、ブルックフィールド型粘度計(BROOKFIELD ENGINEERING LABS.INC.製)を用いて、38℃で測定した値である。
ここで、金属亜鉛換算の担持量とは、担持している酸化亜鉛微粒子又は塩基性炭酸亜鉛微粒子を金属亜鉛に換算したZn換算質量を算出し、この値を用いて、以下の式から算出することができる。
金属亜鉛換算の担持量(質量%)=〔(Zn換算質量)/(微粒子亜鉛担持体の質量)〕×100
BETZn−Si:微粒子亜鉛担持体のBET比表面積
BETSi:珪酸塩粒子のBET比表面積
WZn:微粒子亜鉛担持体中に含まれる酸化亜鉛又は塩基性炭酸亜鉛の質量%
WSi:微粒子亜鉛担持体中に含まれる珪酸塩粒子の質量%
(2)アルカリ性水溶液に珪酸塩粒子を分散させておき、この分散液に、亜鉛塩の酸性水溶液を添加する。
(3)水中に珪酸塩粒子を分散させておき、この分散液に、亜鉛塩の酸性水溶液とアルカリ性水溶液とを同時に添加する。
硫黄としては、ゴム工業において一般的に用いられる粉末硫黄、沈降硫黄、コロイド硫黄、不溶性硫黄、高分散性硫黄、可溶性硫黄などが挙げられる。これらは、単独で用いてもよく、2種以上を併用してもよい。
なお、上記微粒子亜鉛担持体を含有する場合、酸化亜鉛を含有してもよいが、その含有量は少ないほうがよい。
酸化亜鉛としては、従来公知のものを使用でき、例えば、三井金属鉱業(株)、東邦亜鉛(株)、ハクスイテック(株)、正同化学工業(株)、堺化学工業(株)等の製品を使用できる。
なお、上記微粒子亜鉛担持体を含有する場合、酸化亜鉛の含有量は、ゴム成分100質量部に対して、好ましくは0.5質量部以下、より好ましくは0.1質量部以下、更に好ましく0質量部(含まない)である。
老化防止剤としては、例えば、フェニル−α−ナフチルアミン等のナフチルアミン系老化防止剤;オクチル化ジフェニルアミン、4,4′−ビス(α,α′−ジメチルベンジル)ジフェニルアミン等のジフェニルアミン系老化防止剤;N−イソプロピル−N′−フェニル−p−フェニレンジアミン、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、N,N′−ジ−2−ナフチル−p−フェニレンジアミン等のp−フェニレンジアミン系老化防止剤;2,2,4−トリメチル−1,2−ジヒドロキノリンの重合物等のキノリン系老化防止剤;2,6−ジ−t−ブチル−4−メチルフェノール、スチレン化フェノール等のモノフェノール系老化防止剤;テトラキス−[メチレン−3−(3′,5′−ジ−t−ブチル−4′−ヒドロキシフェニル)プロピオネート]メタン等のビス、トリス、ポリフェノール系老化防止剤などが挙げられる。これらは単独で用いてもよいし、2種類以上を組み合わせて用いてもよい。なかでも、p−フェニレンジアミン系老化防止剤が好ましい。
ステアリン酸としては、従来公知のものを使用でき、例えば、日油(株)、NOF社、花王(株)、和光純薬工業(株)、千葉脂肪酸(株)等の製品を使用できる。
ワックスとしては、特に限定されず、パラフィンワックス、マイクロクリスタリンワックス等の石油系ワックス;植物系ワックス、動物系ワックス等の天然系ワックス;エチレン、プロピレン等の重合物等の合成ワックスなどが挙げられる。これらは単独で用いてもよく、2種以上を組み合わせて用いてもよい。なかでも、石油系ワックスが好ましく、パラフィンワックスがより好ましい。
加工助剤としては、特に限定されず、タイヤ工業において一般的なものを使用でき、例えば、脂肪酸金属塩、脂肪酸アミド、アミドエステル、シリカ表面活性剤、脂肪酸エステル、脂肪酸金属塩とアミドエステルとの混合物、脂肪酸金属塩と脂肪酸アミドとの混合物などが使用できる。これらは、単独で用いてもよく、2種以上を併用してもよい。なかでも、脂肪酸金属塩、アミドエステル、脂肪酸金属塩とアミドエステル若しくは脂肪酸アミドとの混合物が好ましく、脂肪酸金属塩と脂肪酸アミドとの混合物が特に好ましい。
加硫促進剤としては、2−メルカプトベンゾチアゾール、ジ−2−ベンゾチアゾリルジスルフィド、N−シクロヘキシル−2−ベンゾチアジルスルフェンアミド等のチアゾール系加硫促進剤;テトラメチルチウラムジスルフィド(TMTD)、テトラベンジルチウラムジスルフィド(TBzTD)、テトラキス(2−エチルヘキシル)チウラムジスルフィド(TOT−N)等のチウラム系加硫促進剤;N−シクロヘキシル−2−ベンゾチアゾールスルフェンアミド、N−t−ブチル−2−ベンゾチアゾリルスルフェンアミド、N−オキシエチレン−2−ベンゾチアゾールスルフェンアミド、N−オキシエチレン−2−ベンゾチアゾールスルフェンアミド、N,N′−ジイソプロピル−2−ベンゾチアゾールスルフェンアミド等のスルフェンアミド系加硫促進剤;ジフェニルグアニジン、ジオルトトリルグアニジン、オルトトリルビグアニジン等のグアニジン系加硫促進剤を挙げることができる。これらは、単独で用いてもよく、2種以上を併用してもよい。なかでも、本発明の効果がより好適に得られるという理由から、スルフェンアミド系加硫促進剤、グアニジン系加硫促進剤が好ましい。
<芳香族ビニル−共役ジエン共重合体1(共重合体1)の製造>
内容積20Lの撹拌装置付きステンレス製重合反応器を、洗浄及び乾燥し、当該重合反応器の内部の雰囲気を乾燥窒素に置換した。次に、工業用ヘキサン(住友化学社製、商品名:ヘキサン(一般品)、密度0.68g/mL)7.65kg、シクロヘキサン2.93kg、1,3−ブタジエン240g、スチレン510g、テトラヒドロフラン8.8mL及びエチレングリコールジブチルエーテル0.9mLを重合反応器内に投入した。次に、重合開始剤の失活に作用する不純物を予め無毒化させるために、スカベンジャーとして少量のn−ブチルリチウム(n−BuLi)のヘキサン溶液を重合反応器内に投入した後、n−BuLiを3.12mmol含有するn−ヘキサン溶液を重合反応器内に投入し、重合反応を開始した。
該撹拌物に2−tert−ブチル−6−(3−tert−ブチル−2−ヒドロキシ−5−メチルベンジル)−4−メチルフェニルアクリレート(住友化学社製、商品名:スミライザーGM)6.0g、ペンタエリスリチルテトラキス(3−ラウリルチオプロピオネート)(住友化学社製、商品名:スミライザーTP−D)3.0g及び伸展油(ジャパンエナジー社製、商品名:JOMOプロセスNC−140)562.5gを加え、混合物を得た。次に、該混合物中の揮発分の大部分を、常温、24時間で蒸発させ、更に55℃で12時間減圧乾燥し、芳香族ビニル−共役ジエン共重合体1(共重合体1)を得た。
<芳香族ビニル−共役ジエン共重合体2(共重合体2)の製造>
内容積20Lの撹拌装置付きステンレス製重合反応器を、洗浄及び乾燥し、当該重合反応器の内部の雰囲気を乾燥窒素に置換した。次に、「ヘキサン(一般品)」7.65kg、シクロヘキサン2.93kg、1,3−ブタジエン298g、スチレン553g、テトラヒドロフラン8.8mL及びエチレングリコールジブチルエーテル0.9mLを重合反応器内に投入した。次に、n−BuLiのヘキサン溶液を重合反応器内に投入した後、n−BuLiを3.06mmol含有するn−ヘキサン溶液を重合反応器内に投入し、重合反応を開始した。
該撹拌物に「スミライザーGM」6.2g及び「スミライザーTP−D」3.1g及び「JOMOプロセスNC−140」580gを加え、混合物を得た。次に、該混合物中の揮発分の大部分を、常温、24時間で蒸発させ、更に55℃で12時間減圧乾燥し、芳香族ビニル−共役ジエン共重合体2(共重合体2)を得た。
<芳香族ビニル−共役ジエン共重合体3(共重合体3)の製造>
内容積20Lの撹拌装置付きステンレス製重合反応器を、洗浄及び乾燥し、当該重合反応器の内部の雰囲気を乾燥窒素に置換した。次に、「ヘキサン(一般品)」7.65kg、シクロヘキサン2.93kg、1,3−ブタジエン240g、スチレン360g、テトラヒドロフラン8.8mL及びエチレングリコールジブチルエーテル0.9mLを重合反応器内に投入した。次に、n−BuLiのヘキサン溶液を重合反応器内に投入した後、n−BuLiを2.64mmol含有するn−ヘキサン溶液を重合反応器内に投入し、重合反応を開始した。
該撹拌物に「スミライザーGM」7.2g及び「スミライザーTP−D」3.6g及び「JOMOプロセスNC−140」450gを加え、混合物を得た。次に、該混合物中の揮発分の大部分を、常温、24時間で蒸発させ、更に55℃で12時間減圧乾燥し、芳香族ビニル−共役ジエン共重合体3(共重合体3)を得た。
<芳香族ビニル−共役ジエン共重合体4(共重合体4)の製造>
内容積20Lの撹拌装置付きステンレス製重合反応器を、洗浄及び乾燥し、当該重合反応器の内部の雰囲気を乾燥窒素に置換した。次に、「ヘキサン(一般品)」7.65kg、シクロヘキサン2.93kg、1,3−ブタジエン240g、スチレン360g、テトラヒドロフラン8.8mL及びエチレングリコールジブチルエーテル0.9mLを重合反応器内に投入した。次に、n−BuLiのヘキサン溶液を重合反応器内に投入した後、n−BuLiを3.12mmol含有するn−ヘキサン溶液を重合反応器内に投入し、重合反応を開始した。
該撹拌物に「スミライザーGM」8.0g及び「スミライザーTP−D」4.0g及び「JOMOプロセスNC−140」562.5gを加え、混合物を得た。次に、該混合物中の揮発分の大部分を、常温、24時間で蒸発させ、更に55℃で12時間減圧乾燥し、芳香族ビニル−共役ジエン共重合体4(共重合体4)を得た。
赤外分光分析法により、ビニル基の吸収ピークである910cm−1付近の吸収強度より、共重合体における共役ジエンのビニル結合量を求めた。
JIS K6383(1995)に従って、屈折率から共重合体中のスチレン単位の含有量を求めた。
下記の条件(1)〜(8)でゲルパーミエーションクロマトグラフ(GPC)法により、Mwを測定した。
(1)装置:島津製作所製 Prominence
(2)分離カラム:Agilent社製 PLgel 5μm 105Å、PLgel 5μm 106Å(各1本を連結)
(3)測定温度:40℃
(4)キャリア:テトラヒドロフラン
(5)流量:1.0mL/分
(6)注入量:100μL
(7)検出器:示差屈折
(8)分子量標準:標準ポリスチレン
重クロロホルムを溶媒として用い、400MHzの1H−NMR(日本電子製 AL400)を測定し、共重合体の構造解析を行った。得られたNMRスペクトルより、スチレン単位のシークエンスの状態を以下の範囲の積分値から求めた。孤立スチレン単位の含有割合は、下記(a)〜(c)の積分値の合計に対して、下記(a)の積分値から、(b)と(c)より求められる芳香環のメタ位及びパラ位プロトンの計算値を引いた積分値の割合とした。
(a)孤立スチレン単位、2〜3連鎖スチレン、4連鎖以上スチレン:7.6〜7.0ppm間のピークの積分値。
(b)2〜3連鎖スチレン(オルト位プロトン):7.0〜6.9ppm間のピークの積分値。
(c)4連鎖以上スチレン(オルト位プロトン):6.9〜6.0ppm間のピークの積分値。
株式会社日立ハイテクサイエンス製の示差走査熱分析装置DSC7020を用い、共重合体を窒素雰囲気下で−100℃まで冷却した後に10℃/分で100℃まで昇温する条件で測定した。得られる熱流曲線の転移によるベースラインシフトの外挿開始点と外挿終了点との差をΔTgとして読み取った。
<微粒子亜鉛担持体の製造>
5.5質量%濃度の焼成クレー水懸濁液847mlに、酸化亜鉛を91.5g加えて十分に攪拌した。ついで、10質量%濃度の炭酸ナトリウム水溶液を330gと、10質量%塩化亜鉛水溶液を340g加えてさらに攪拌した。これに30質量%濃度の炭酸ガスを、pHが7以下になるまで吹き込んで、焼成クレーの表面に塩基性炭酸亜鉛を析出させて微粒子亜鉛担持体を合成した。その後、脱水、乾燥、粉砕工程を経て粉末化し、微粒子亜鉛担持体を得た。
<カーボンブラックB、Cの製造>
空気導入ダクトと燃焼バーナーを備える内径1100mm、長さ1700mmの燃焼帯域、該燃焼帯域から連接され、周辺から原料ノズルを貫通接続した内径175mm、長さ1050mmの狭径部からなる原料導入帯域、クエンチ装置を備えた内径400mm、長さ3000mmの後部反応帯域を順次接合したカーボンブラック反応炉を用い、燃料油にD重油、及び原料炭化水素(原料油)にクレオソート油を使用し、表2に示す各条件によりカーボンブラックを製造した。
さらに、酸素を流通しない条件下(窒素ガス雰囲気下)で表2に示す条件により熱処理を行った。
各製造例により得られたカーボンブラックの各種特性を表2に示した。なお、各特性の測定は、上述の方法により行った。
<変性共役ジエン系重合体の製造>
(共役ジエン系重合体の合成)
あらかじめ、0.18ミリモルのバーサチック酸ネオジムを含有するシクロヘキサン溶液、3.6ミリモルのメチルアルモキサンを含有するトルエン溶液、6.7ミリモルの水素化ジイソブチルアルミニウムを含有するトルエン溶液、及び、0.36ミリモルのトリメチルシリルアイオダイドを含有するトルエン溶液と1,3−ブタジエン0.90ミリモルを30℃で60分間反応熟成させて得られる触媒組成物(ヨウ素原子/ランタノイド含有化合物(モル比)=2.0)を得た。続いて、シクロヘキサン2.4kg、1,3−ブタジエン300gを窒素置換された5Lオートクレーブに投入した。そして、上記触媒組成物を上記オートクレーブに投入し、30℃で2時間、重合反応させて、重合体溶液を得た。なお、投入した1,3−ブタジエンの反応転化率は、ほぼ100%であった。
JIS K 6300に準じて、Lローターを使用して、予熱1分、ローター作動時間4分、温度100℃の条件で測定した。
ゲルパーミエーションクロマトグラフ(商品名;HLC−8120GPC、東ソー社製)を使用し、検知器として、示差屈折計を用いて、以下の条件で測定し、標準ポリスチレン換算値として算出した。
カラム ;商品名「GMHHXL」、(東ソー社製)2本、
カラム温度 ;40℃、
移動相 ;テトラヒドロフラン、
流速 ;1.0ml/分、
サンプル濃度;10mg/20ml
シス−1,4−結合の含量、及び1,2−ビニル結合の含量は、1H−NMR分析及び13C−NMR分析により測定を行った。NMR分析には、日本電子社製の商品名「EX−270」を使用した。具体的には、1H−NMR分析としては、5.30〜5.50ppm(1,4−結合)、及び4.80−5.01ppm(1,2−結合)におけるシグナル強度から、重合体中の1,4−結合と1,2−結合の比を算出した。更に、13C−NMR分析としては、27.5ppm(シス−1,4−結合)、及び32.8ppm(トランス−1,4−結合)におけるシグナル強度から、重合体中のシス−1,4−結合とトランス−1,4−結合の比を算出した。これらの算出した値の比率を算出し、シス−1,4−結合量(質量%)及び1,2−ビニル結合量(質量%)とした。
変性共役ジエン系重合体(以下、「変性重合体」とも称する。)を得るために、上記共役ジエン系重合体の重合体溶液に次の処理を行った。温度30℃に保持した重合体溶液に、1.71ミリモルの3−グリシドキシプロピルトリメトキシシランを含有するトルエン溶液を添加し、30分間反応させて反応溶液を得た。それから、この反応溶液に1.71ミリモルの3−アミノプロピルトリエトキシシランを含有するトルエン溶液を添加し、30分間撹拌した。続いて、この反応溶液に1.28ミリモルのテトライソプロピルチタネートを含有するトルエン溶液を添加し、30分間撹拌した。その後、重合反応を停止させるため、2,4−ジ−tert−ブチル−p−クレゾールを1.5g含むメタノール溶液を添加して、この溶液を変性重合体溶液とした。収量は2.5kgであった。続いて、この変性重合体溶液に、水酸化ナトリウムによりpH10に調整した水溶液20Lを添加し、110℃で2時間、脱溶媒とともに縮合反応させた。その後、110℃のロールで乾燥して、得られた乾燥物を変性重合体とした。
JIS K 6300に準じて、Lローターを使用して、予熱1分、ローター作動時間4分、温度125℃の条件で測定した。
圧力3.5lb/in2、温度50℃で重合体を1/4インチオリフィスに通して押し出すことにより測定した。定常状態にするため、10分間放置後、押し出し速度を測定し、その測定値を毎分のミリグラム数(mg/分)で表示した。
90℃の恒温槽で2日間保存した後のムーニー粘度(ML1+4,125℃)を測定し、下記式により算出した値である。なお、値が小さいほど経時安定性が良好である。
式:[90℃の恒温槽で2日間保存した後のムーニー粘度(ML1+4,125℃)]−[合成直後に測定したムーニー粘度(ML1+4,125℃)]
ガラス転移温度は、JIS K 7121に準じて、ティー・エイ・インスツルメント・ジャパン社製の示差走査熱量計(Q200)を用いて昇温速度10℃/分で昇温しながら測定することによリ、ガラス転移開始温度として求めた。
共重合体1〜4:製造例1〜4で製造
変性共役ジエン系重合体:製造例8で製造
天然ゴム:TSR20
ブタジエンゴム:宇部興産(株)製のウベポールBR150B
シリカA:ソルベイジャパン(株)製の115GR(N2SA:115m2/g)
シリカB:エボニック社製のVN3(N2SA:175m2/g)
シリカC:エボニック社製の9000GR(N2SA:235m2/g)
シランカップリング剤A:エボニック社製のSi69(ビス(3−トリエトキシシリルプロピル)テトラスルフィド)
シランカップリング剤B:モメンティブ社製のNXT(3−オクタノイルチオ−1−プロピルトリエトキシシラン)
シランカップリング剤C:モメンティブ社製のNXT−Z45(結合単位A及び結合単位Bの共重合体(結合単位A:55モル%、結合単位B:45モル%))
カーボンブラックA:三菱化学(株)製のダイアブラックN339(N2SA:96m2/g、DBP吸収量:124ml/100g)
カーボンブラックB:製造例6で製造
カーボンブラックC:製造例7で製造
レジンA:ヤスハラケミカル(株)製のYSレジンPX1150N(ポリテルペン(β−ピネン樹脂)、軟化点:115℃)
レジンB:ヤスハラケミカル(株)製のYSポリスターT160(テルペンフェノール樹脂、軟化点:160℃)
レジンC:丸善石油化学(株)製のマルカレッツM−890A(ジシクロペンタジエン系樹脂、軟化点:105℃)
レジンD:荒川化学工業(株)製のパインクリスタルKR−85(ロジン系樹脂、軟化点:80〜87℃)
レジンE:アリゾナケミカル社製のSYLVARES SA85(α−メチルスチレン及びスチレンの共重合体、軟化点:85℃)
オイル:JX日鉱日石エネルギー(株)製のX−140(芳香族系プロセスオイル)
ファルネセン系樹脂A:(株)クラレ製のKB−101(ファルネセン単独重合体、Mw:10000、溶融粘度:0.7Pa・s、Tg:−72℃)
ファルネセン系樹脂B:(株)クラレ製のFSR−221(ファルネセン−スチレン共重合体、Mw:10000、質量基準の共重合比:ファルネセン/スチレン=77/23、溶融粘度:5.7Pa・s、Tg:−54℃)
ファルネセン系樹脂C:(株)クラレ製のFBR−746(ファルネセン−ブタジエン共重合体、Mw:100000、質量基準の共重合比:ファルネセン/ブタジエン=60/40、溶融粘度:603Pa・s、Tg:−78℃)
老化防止剤:住友化学(株)製のアンチゲン3C
ステアリン酸:日油(株)製のビーズステアリン酸つばき
酸化亜鉛:三井金属鉱業(株)製の亜鉛華1号
微粒子亜鉛担持体:製造例5で製造
ワックス:大内新興化学工業(株)製のサンノックN
加工助剤:ストラクトール社製のWB16(脂肪酸金属塩(脂肪酸カルシウム、構成脂肪酸:炭素数14〜20の飽和脂肪酸)と脂肪酸アミドとの混合物)
硫黄:鶴見化学工業(株)製の粉末硫黄
加硫促進剤1:住友化学(株)製のソクシノールCZ(N−シクロヘキシル−2−ベンゾチアゾリルスルフェンアミド)
加硫促進剤2:住友化学(株)製のソクシノールD(1,3−ジフェニルグアニジン)
テトラジン系化合物A:上記式(1−1−1)で表される化合物
テトラジン系化合物B:上記式(1−2−1)で表される化合物
表3〜12に示す配合内容に従い、(株)神戸製鋼所製の1.7Lバンバリーミキサーを用いて、硫黄及び加硫促進剤以外の材料を150℃の条件下で5分間混練りし、混練り物を得た。次に、得られた混練り物に硫黄及び加硫促進剤を添加し、オープンロールを用いて、80℃の条件下で5分間練り込み、未加硫ゴム組成物を得た。得られた未加硫ゴム組成物を170℃で20分間、0.5mm厚の金型でプレス加硫し、加硫ゴム組成物を得た。
また、得られた未加硫ゴム組成物をキャップトレッドの形状に成形し、タイヤ成型機上で他のタイヤ部材とともに貼り合わせて未加硫タイヤを形成し、170℃で12分間加硫し、試験用タイヤ(サイズ:195/65R15)を製造した。
以下の評価において、表3の基準比較例を比較例1−1、表4の基準比較例を比較例2−1、・・・、表12の基準比較例を比較例10−1とした。
LAT試験機(Laboratory Abrasion and Skid Tester)を用い、荷重50N、速度20km/h、スリップアングル5°の条件で、加硫ゴム組成物の容積損失量を測定した。基準比較例の容積損失量を100として指数表示した(耐摩耗性能指数)。指数が大きいほど、耐摩耗性能に優れることを示している。
(株)上島製作所製スペクトロメーターを用い、動的歪振幅1%、周波数10Hz、温度50℃の条件で、加硫ゴム組成物のtanδを測定した。基準比較例のtanδを100として指数表示した(低燃費性能指数)。指数が大きいほど、転がり抵抗が小さく、低燃費性能に優れることを示している。
各試験用タイヤを車両(国産FF2000cc)の全輪に装着して、湿潤アスファルト路面にて初速度100km/hからの制動距離を求めた。基準比較例の制動距離を100として指数表示した(ウェットグリップ性能指数)。指数が大きいほど、ウェットグリップ性能に優れることを示している。
Claims (12)
- 芳香族ビニル化合物に基づく芳香族ビニル単位及び共役ジエン化合物に基づく共役ジエン単位を有する芳香族ビニル−共役ジエン共重合体を含むゴム成分と、カーボンブラックと、窒素吸着比表面積が40m2/g以上のシリカとを含有するタイヤ用ゴム組成物であって、
前記共重合体が、前記芳香族ビニル単位の全量を基準として、孤立芳香族ビニル単位を80%以上含み、示差走査熱量測定における前記共重合体のガラス転移温度幅が10℃より大きく20℃未満であり、
前記ゴム成分100質量%中、前記共重合体の含有量が1〜60質量%、イソプレン系ゴムの含有量が0〜99質量%であり、
前記シリカの含有量が前記ゴム成分100質量部に対して10質量部以上であるタイヤ用ゴム組成物。 - 珪酸塩粒子の表面に酸化亜鉛微粒子又は塩基性炭酸亜鉛微粒子を担持させた微粒子亜鉛担持体を含有する請求項1記載のタイヤ用ゴム組成物。
- 前記シリカの窒素吸着比表面積が160m2/g以上である請求項1又は2記載のタイヤ用ゴム組成物。
- 前記カーボンブラックの圧縮試料オイル吸収量が100〜180ml/100gである請求項1〜3のいずれかに記載のタイヤ用ゴム組成物。
- 前記シリカの含有量が前記ゴム成分100質量部に対して90質量部以上である請求項1〜4のいずれかに記載のタイヤ用ゴム組成物。
- 可塑剤の含有量が前記ゴム成分100質量部に対して50質量部以上である請求項1〜5のいずれかに記載のタイヤ用ゴム組成物。
- レジンを含有する請求項1〜6のいずれかに記載のタイヤ用ゴム組成物。
- 前記ゴム成分が、変性ポリマーを含む請求項1〜7のいずれかに記載のタイヤ用ゴム組成物。
- メルカプト系シランカップリング剤を含有する請求項1〜9のいずれかに記載のタイヤ用ゴム組成物。
- ファルネセンを重合して得られるファルネセン系樹脂を含有する請求項1〜10のいずれかに記載のタイヤ用ゴム組成物。
- 請求項1〜11のいずれかに記載のタイヤ用ゴム組成物を用いて作製したキャップトレッドを有する空気入りタイヤ。
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WO2022103060A1 (ko) * | 2020-11-16 | 2022-05-19 | 주식회사 엘지화학 | 변성 공액디엔계 중합체 및 이를 포함하는 고무 조성물 |
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