JP2016533427A - 処理フィラー、それを含有する組成物およびそれから調製される物品 - Google Patents
処理フィラー、それを含有する組成物およびそれから調製される物品 Download PDFInfo
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- JP2016533427A JP2016533427A JP2016546900A JP2016546900A JP2016533427A JP 2016533427 A JP2016533427 A JP 2016533427A JP 2016546900 A JP2016546900 A JP 2016546900A JP 2016546900 A JP2016546900 A JP 2016546900A JP 2016533427 A JP2016533427 A JP 2016533427A
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- IOLWRXMELRWXQY-UHFFFAOYSA-N 2-[4-(chloromethyl)phenyl]ethyl-trimethoxysilane Chemical compound CO[Si](OC)(OC)CCC1=CC=C(CCl)C=C1 IOLWRXMELRWXQY-UHFFFAOYSA-N 0.000 claims description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 3
- OXGPXSALMHTDHQ-UHFFFAOYSA-N 3-chloroprop-1-enyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)C=CCCl OXGPXSALMHTDHQ-UHFFFAOYSA-N 0.000 claims description 3
- HFQOZNKPLKXDTP-UHFFFAOYSA-N 3-chloroprop-1-enyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C=CCCl HFQOZNKPLKXDTP-UHFFFAOYSA-N 0.000 claims description 3
- OXYZDRAJMHGSMW-UHFFFAOYSA-N 3-chloropropyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)CCCCl OXYZDRAJMHGSMW-UHFFFAOYSA-N 0.000 claims description 3
- MEWGTFVEQWELBF-UHFFFAOYSA-N [4-(chloromethyl)phenyl]-triethoxysilane Chemical compound CCO[Si](OCC)(OCC)C1=CC=C(CCl)C=C1 MEWGTFVEQWELBF-UHFFFAOYSA-N 0.000 claims description 3
- ZXOFHTCCTUEJQJ-UHFFFAOYSA-N [4-(chloromethyl)phenyl]-trimethoxysilane Chemical compound CO[Si](OC)(OC)C1=CC=C(CCl)C=C1 ZXOFHTCCTUEJQJ-UHFFFAOYSA-N 0.000 claims description 3
- YKTSYUJCYHOUJP-UHFFFAOYSA-N [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] Chemical group [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] YKTSYUJCYHOUJP-UHFFFAOYSA-N 0.000 claims description 3
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- SKSOAAKYLIWZKU-UHFFFAOYSA-N triethoxy-[2-(4-methylphenyl)ethyl]silane Chemical compound CCO[Si](OCC)(OCC)CCC1=CC=C(C)C=C1 SKSOAAKYLIWZKU-UHFFFAOYSA-N 0.000 claims description 3
- PNVQXNRVDYKIKF-UHFFFAOYSA-N trimethoxy-[2-(4-methylphenyl)ethyl]silane Chemical compound CO[Si](OC)(OC)CCC1=CC=C(C)C=C1 PNVQXNRVDYKIKF-UHFFFAOYSA-N 0.000 claims description 3
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- 125000006038 hexenyl group Chemical group 0.000 claims description 2
- 125000001261 isocyanato group Chemical group *N=C=O 0.000 claims description 2
- PAZHGORSDKKUPI-UHFFFAOYSA-N lithium metasilicate Chemical compound [Li+].[Li+].[O-][Si]([O-])=O PAZHGORSDKKUPI-UHFFFAOYSA-N 0.000 claims description 2
- 229910052912 lithium silicate Inorganic materials 0.000 claims description 2
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- NNHHDJVEYQHLHG-UHFFFAOYSA-N potassium silicate Chemical compound [K+].[K+].[O-][Si]([O-])=O NNHHDJVEYQHLHG-UHFFFAOYSA-N 0.000 claims description 2
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- JECYNCQXXKQDJN-UHFFFAOYSA-N 2-(2-methylhexan-2-yloxymethyl)oxirane Chemical compound CCCCC(C)(C)OCC1CO1 JECYNCQXXKQDJN-UHFFFAOYSA-N 0.000 claims 3
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- 125000003118 aryl group Chemical group 0.000 description 20
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Abstract
Description
本出願は、2013年10月7日に出願された米国仮特許出願第61/887,713号の利益を主張し、これにより、この米国仮特許出願は、その全体が本明細書に参考として援用される。
本発明は、処理フィラーの調製プロセス、そのプロセスにより製造された処理フィラー、ならびにこのような処理フィラーを含む組成物および物品に関する。
乗用車やトラックタイヤの転がり抵抗を減らし、湿潤牽引力を向上させるためのシリカ/シランフィラー系の使用については、当該技術分野において公知である。転がり抵抗を減らすと燃料消費量が少なくなる。
本発明では、(a)あらかじめ乾燥させていない未処理フィラーを含むスラリーを、処理剤を含む処理組成物で処理し、それにより処理フィラースラリーを形成させること、および(b)上記処理フィラースラリーを乾燥させて処理フィラーを製造することを含む処理フィラーの製造プロセスが提供される。処理剤は、(i)未処理フィラーと相互作用する少なくとも一つの第1の基および(ii)処理フィラーが混ぜ合わされるゴムマトリックスと相互作用する少なくとも一つの第2の基を有するポリマーを含み得る。
すでに述べたように、本発明は、処理フィラーを製造するプロセスを提供する。上記プロセスは、(a)あらかじめ乾燥させていない未処理フィラーを含み得るスラリーを、処理剤を含む処理組成物で処理し、それにより処理フィラースラリーを形成させること、および(b)処理フィラースラリーを乾燥させて処理フィラーを製造することを含むことができる。
(R1)a(R2)bSiX4−a−b (I)
で表されるものが含まれる。式(I)では、R1は、それぞれの「a」に対して独立に、1〜36個の炭素原子および官能基を有するヒドロカルビル基である。ヒドロカルビル基の官能基は、ビニル、アリル、ヘキセニル、エポキシ(オキシラン)、グリシドキシ、(メタ)アクリルオキシ、スルフィド、イソシアナト(−NCO)、ポリスルフィド、メルカプト、またはハロゲンである。式(I)では、R2は、それぞれの「b」に対して独立に、1〜36個の炭素原子を有するヒドロカルビル基または水素である。式(I)のXは、独立に、ハロゲンまたは1〜36個の炭素原子を有するアルコキシであり;下付き文字の「a」は、0、1、2または3であり;下付き文字の「b」は、0、1または2であり;(a+b)は、1、2または3である。但し、いくつかの実施形態では、bが1の場合、(a+b)は2または3である。本発明のいくつかのさらなる実施形態では、処理組成物は、式(I)で表されるカップリング剤をさらに含み、この場合、Xはアルコキシであり;aは1であり;bは0であり;R1のヒドロカルビルの官能基はハロゲンである。
(R3)c(R4)dSiY4−c−d (II)
で表されるオルガノシランを挙げることができる。式(II)では、R3はそれぞれの「c」に対して独立に、1〜12個の炭素原子および官能基を有するヒドロカルビル基であってよい。官能基は、スルフィドであっても、ポリスルフィドであっても、メルカプトであってもよい。式(II)では、R4は、それぞれの「d」に対して独立に、1〜18個の炭素原子を有するヒドロカルビル基であっても、水素であってもよい。それぞれのYは、それぞれ独立に、ハロゲンであっても、1〜12個の炭素原子を有するアルコキシ基であってもよい。下付き文字の「c」は、0、1、2または3であり得;下付き文字の「b」は、0、1または2であり得;c+dは、1、2または3であり得る。但し、いくつかの実施形態では、bが1の場合、a+bは、2または3である。式(II)のR3およびR4基は、処理フィラーを混ぜ合わせることができるポリマー組成物と反応することが可能なように選択され得る。
さらに、硫黄含有オルガノシランは、次の式(III)
Z’−alk−Sn’−alk−Z’ (III)
で表されるビス(アルコキシシリルアルキル)ポリスルフィドを含み得る。式(III)では、「alk」は1〜18個の炭素原子を有する二価の炭化水素ラジカルを表し、n’は2〜12の整数であり、Z’は
3,3’−ビス(トリメトキシシリルプロピル)ジスルフィド、3,3’−ビス(トリエトキシシリルプロピル)テトラスルフィド、
3,3’−ビス(トリメトキシシリルプロピル)テトラスルフィド、2,2’−ビス(トリエトキシシリルエチル)テトラスルフィド、
3,3’−ビス(トリメトキシシリルプロピル)トリスルフィド、3,3’−ビス(トリエトキシシリルプロピル)トリスルフィド、
3,3’−ビス(トリブトキシシリルプロピル)ジスルフィド、3,3’−ビス(トリメトキシシリルプロピル)ヘキサスルフィド、および
3,3’−ビス(トリオクトキシシリルプロピル)テトラスルフィド、ならびにこれらの混合物。
また、硫黄含有オルガノシランは、次の式(IV)
(a)アルカリ金属シリケートと酸を組み合わせて、未処理スラリーを形成させること;
(b)任意選択的に、未処理スラリーを、処理剤を含む処理組成物で処理して処理スラリーを形成させること;
(c)(a)の未処理スラリーを乾燥して、または(b)の処理スラリーを乾燥して、いずれの場合にも、乾燥沈殿シリカを生成すること;
(d)処理剤を含む処理組成物と共に、ステップ(c)の乾燥沈殿シリカの水性スラリーを形成させ、処理シリカスラリーを形成させること;および
(e)処理シリカスラリーを乾燥して、乾燥処理沈殿シリカを製造することを含む、処理沈殿シリカを製造するプロセスに関する。
本出願の実施例で報告したシリカのCTAB表面積値は、CTAB溶液および以下に記載の方法を使って測定した。Metrohm Interchangeable「Snap−In」50ミリリットルビュレットを装着したMetrohm 751 Titrino自動滴定装置、および550nmフィルターを装着したBrinkmann Probe Colorimeter Model PC 910を用いて分析を行った。加えて、Mettler Toledo HB43または同等装置を使用して105℃でのシリカの水分損失を測定し、シリカと残留CTAB溶液を分離するためにFisher Scientific Centrific(商標)Centrifuge Model 225を使用した。過剰のCTABは、AEROSOL(登録商標)OT(ジオクチルナトリウムスルホスクシネート;Cytec Industries,Incから入手可能)の溶液で最大濁度が得られるまで自動滴定により測定し、この最大濁度は、プローブ比色計で検出した。最大濁度点は、150ミリボルトの読みに対応するものとして取得した。所与の重量のシリカに吸着したCTABの量と、CTAB分子により占められている空間がわかったのち、シリカの外側比表面積を計算し、乾燥重量基準で平方メートル/グラムとして報告した。
実施例B.
実施例E
機械での撹拌下、約2000gの約7%固形物シリカスラリーを5Lの三つ口フラスコに加えた。反応器温度を87℃に設定し、SiO2固形物に対し5.5重量%の3−メルカプトプロピルトリエトキシシランをゆっくり添加した。シランの添加完了後、SiO2固形物に対し6重量%のカルボキシル化SBRラテックスのGenflo3810を反応器に加えた。スラリーのpHを濃硫酸を用いて4.5に調整した。得られた生成物をDI水を使って漏斗で洗浄した。脱イオン水を使って材料を12%固形物に再度スラリー化した。その後、ミニBuchiスプレードライヤーを使ってスラリーを乾燥した。入口温度を180〜185℃に設定し、出口温度を90〜92℃に設定した。アスピレータを80%に設定し、ポンプを22%に設定した。空気圧は80psiであった。乾燥シリカの特性を表23に示す。
Claims (38)
- 処理フィラーの製造プロセスであって、前記プロセスが、
(a)あらかじめ乾燥させていない未処理フィラーを含むスラリーを、処理剤を含む処理組成物で処理し、それにより処理フィラースラリーを形成させる工程、および
(b)前記処理フィラースラリーを乾燥させて処理フィラーを製造する工程を含み、
前記処理剤が、(i)前記未処理フィラーと相互作用する少なくとも一つの第1の基および(ii)前記処理フィラーが混ぜ合わされるゴムマトリックスと相互作用する少なくとも一つの第2の基を含むポリマーを含む、プロセス。 - 前記未処理フィラーが、ケイ酸アルミニウム、シリカゲル、コロイド状シリカ、沈殿シリカ、およびこれらの混合物から選択される、請求項1に記載のプロセス。
- 前記フィラーが沈殿シリカを含む、請求項1に記載のプロセス。
- 前記ポリマーが、アクリルポリマー、スチレンブタジエンラテックス、天然ゴムラテックス、またはこれらの組合せから選択される、請求項1に記載のプロセス。
- 前記アクリルポリマーが、アクリルランダムコポリマー、アクリル櫛状ポリマー、アクリルブロックコポリマー、超分岐アクリルポリマー、またはこれらの組合せから選択される、請求項4に記載のプロセス。
- 前記超分岐アクリルポリマーが、少なくとも部分的に前記処理フィラーを封入する、請求項5に記載のプロセス。
- 前記少なくとも一つの第1の基が、エステル、カルボン酸、イミド、無水物、二塩基酸、ラクトン、オキシラン、イソシアネート、アルコキシシラン、これらの加水分解生成物、これらの塩、またはこれらの組合せから選択される、請求項1に記載のプロセス。
- 前記少なくとも一つの第2の基が、ホルミル、ケト、チオール、スルフィド、ハロ、アミノ、アルケニル、アルキニル、アルキル、これらの加水分解生成物、これらの塩、またはこれらの組合せから選択される、請求項1に記載のプロセス。
- 前記少なくとも一つの第2の基が、ヒドロキシル、無水物、オキシラン、これらの加水分解生成物、これらの塩、またはこれらの組合せから選択される、請求項1に記載のプロセス。
- 前記処理組成物が、式(II)により表されるオルガノシランカップリング剤
(R1)a(R2)bSiX4−a−b (II)
をさらに含み、
式中、各R1は、独立に、1〜36個の炭素原子および官能基を含むヒドロカルビル基であり、前記ヒドロカルビル基の前記官能基は、ビニル、アリル、ヘキセニル、エポキシ、グリシドキシ、(メタ)アクリルオキシ、スルフィド、イソシアナト、ポリスルフィド、メルカプト、またはハロゲンであり;各R2は、独立に、1〜36個の炭素原子を有するヒドロカルビル基または水素であり、Xは、独立に、ハロゲンまたは1〜36個の炭素原子を有するアルコキシであり、aは、0、1、2、または3であり、bは、0、1、または2であり、(a+b)は、1、2、または3であるが、ただし、bが1の場合は、(a+b)は2または3である、請求項1に記載のプロセス。 - 前記処理組成物が、式(II)で表される前記オルガノシランとは異なるオルガノシランをさらに含む、請求項10に記載のプロセス。
- 前記処理組成物が、(4−クロロメチル−フェニル)トリメトキシシラン、(4−クロロメチル−フェニル)トリエトキシシラン、[2−(4−クロロメチル−フェニル)−エチル]トリメトキシシラン、[2−(4−クロロメチル−フェニル)−エチル]トリエトキシシラン、(3−クロロ−プロペニル)−トリメトキシシラン、(3−クロロ−プロペニル)−トリエトキシシラン、(3−クロロ−プロピル)−トリエトキシシラン、(3−クロロ−プロピル)−トリメトキシシラン、トリメトキシ−(2−p−トリル−エチル)シランおよびトリエトキシ−(2−p−トリル−エチル)シラン、およびこれらの組合せからなる群から選択されるオルガノシランを含むカップリング剤をさらに含む、請求項1に記載のプロセス。
- 前記処理組成物が、前記処理剤とは異なる非カップリング剤をさらに含み、前記処理剤とは異なる前記非カップリング剤が、生体高分子、脂肪酸、有機酸、ポリマーエマルジョン、ポリマーコーティング組成物、およびこれらの組合せのうちの一つまたは複数である、請求項1に記載のプロセス。
- 前記処理組成物が、アニオン性界面活性剤、非イオン性界面活性剤、両性界面活性剤、およびこれらの組合せから選択され、未処理フィラーの重量を基準にして1重量%超〜25重量%の量で存在する非カップリング剤をさらに含む、請求項1に記載のプロセス。
- 前記処理フィラーが処理沈殿シリカを含み、
前記処理組成物が、
(i)少なくとも1種のカップリング剤と、
(ii)アニオン性、非イオン性、および/または両性界面活性剤から選択され、未処理フィラーの重量を基準にして1重量%超〜25重量%の量で存在する非カップリング剤とをさらに含む、請求項1に記載のプロセス。 - 請求項1に記載のプロセスにより製造された処理フィラー。
- 請求項1に記載のプロセスにより製造された前記処理フィラーを含むゴム組成物。
- 前記ゴム組成物が天然ゴムを含む、請求項17に記載のゴム組成物。
- ゴム配合マスターバッチである、請求項17に記載のゴム組成物。
- 処理沈殿シリカの製造プロセスであって、前記プロセスが、
(a)アルカリ金属シリケートと酸とを組み合わせて、あらかじめ乾燥させていない未処理シリカを含むスラリーを形成させる工程、
(b)前記スラリーを、処理剤を含む処理組成物で処理し、それにより処理スラリーを形成させる工程、および
(c)前記処理スラリーを乾燥させて、処理沈殿シリカを製造する工程を含み、
前記処理剤が、(i)前記未処理シリカと相互作用する少なくとも一つの第1の基および(ii)前記処理シリカが混ぜ合わされるゴムマトリックスと相互作用する少なくとも一つの第2の基を含むポリマーを含む、プロセス。 - 前記ポリマーが、アクリルポリマー、スチレンブタジエンラテックス、天然ゴムラテックス、またはこれらの組合せから選択される、請求項20に記載のプロセス。
- 前記アクリルポリマーが、アクリルランダムコポリマー、アクリル櫛状ポリマー、アクリルブロックコポリマー、超分岐アクリルポリマー、またはこれらの組合せから選択される、請求項21に記載のプロセス。
- 前記超分岐アクリルポリマーが、少なくとも部分的に前記処理フィラーを封入する、請求項22に記載のプロセス。
- 前記少なくとも一つの第1の基が、エステル、カルボン酸、イミド、無水物、二塩基酸、ラクトン、オキシラン、イソシアネート、アルコキシシラン、これらの加水分解生成物、これらの塩、またはこれらの組合せから選択される、請求項20に記載のプロセス。
- 前記少なくとも一つの第2の基が、ホルミル、ケト、チオール、スルフィド、ハロ、アミノ、アルケニル、アルキニル、アルキル、これらの加水分解生成物、これらの塩、またはこれらの組合せから選択される、請求項20に記載のプロセス。
- 前記少なくとも一つの第2の基が、ヒドロキシル、無水物、オキシラン、これらの加水分解生成物、これらの塩、またはこれらの組合せから選択される、請求項20に記載のプロセス。
- 前記アルカリ金属シリケートが、ケイ酸アルミニウム、ケイ酸リチウム、ケイ酸ナトリウム、および/またはケイ酸カリウムを含む、請求項20に記載のプロセス。
- 前記処理組成物が、(4−クロロメチル−フェニル)トリメトキシシラン、(4−クロロメチル−フェニル)トリエトキシシラン、[2−(4−クロロメチル−フェニル)−エチル]トリメトキシシラン、[2−(4−クロロメチル−フェニル)−エチル]トリエトキシシラン、(3−クロロ−プロペニル)−トリメトキシシラン、(3−クロロ−プロペニル)−トリエトキシシラン、(3−クロロ−プロピル)−トリエトキシシラン、(3−クロロ−プロピル)−トリメトキシシラン、トリメトキシ−(2−p−トリル−エチル)シランおよびトリエトキシ−(2−p−トリル−エチル)シラン、およびこれらの組合せからなる群から選択されるオルガノシランを含むカップリング剤をさらに含む、請求項20に記載のプロセス。
- 前記処理組成物が、アニオン性界面活性剤、非イオン性界面活性剤、両性界面活性剤、およびこれらの組合せから選択され、未処理フィラーの重量を基準にして1重量%超〜25重量%の量で存在する非カップリング剤をさらに含む、請求項20に記載のプロセス。
- 処理沈殿シリカの製造プロセスであって、前記プロセスが、
(a)アルカリ金属シリケートと酸とを組み合わせて、あらかじめ乾燥させていない未処理シリカを含む未処理スラリーを形成させる工程;
(b)前記未処理スラリーを乾燥して、乾燥沈殿シリカを生成する工程;
(c)処理剤および、任意選択的にカップリング剤および/または任意選択的に非カップリング剤を含む処理組成物と共に、前記乾燥沈殿シリカの水性スラリーを形成させ、処理沈殿シリカスラリーを形成させる工程、および
(d)前記処理沈殿シリカスラリーを乾燥して、乾燥処理沈殿シリカを製造する工程を含み、
前記処理剤が、(i)前記未処理シリカと相互作用する少なくとも一つの第1の基および(ii)前記処理シリカが混ぜ合わされるゴムマトリックスと相互作用する少なくとも一つの第2の基を含むポリマーを含む、プロセス。 - 前記ポリマーが、アクリルポリマー、スチレンブタジエンラテックス、天然ゴムラテックス、またはこれらの組合せから選択される、請求項30に記載のプロセス。
- 前記アクリルポリマーが、アクリルランダムコポリマー、アクリル櫛状ポリマー、アクリルブロックコポリマー、超分岐アクリルポリマー、またはこれらの組合せから選択される、請求項31に記載のプロセス。
- 前記超分岐アクリルポリマーが、少なくとも部分的に前記処理フィラーを封入する、請求項32に記載のプロセス。
- 前記少なくとも一つの第1の基が、エステル、カルボン酸、イミド、無水物、二塩基酸、ラクトン、オキシラン、イソシアネート、アルコキシシラン、これらの加水分解生成物、これらの塩、またはこれらの組合せから選択される、請求項30に記載のプロセス。
- 前記少なくとも一つの第2の基が、ホルミル、ケト、チオール、スルフィド、ハロ、アミノ、アルケニル、アルキニル、アルキル、これらの加水分解生成物、これらの塩、またはこれらの組合せから選択される、請求項30に記載のプロセス。
- 前記少なくとも一つの第2の基が、ヒドロキシル、無水物、オキシラン、これらの加水分解生成物、これらの塩、またはこれらの組合せから選択される、請求項30に記載のプロセス。
- 請求項30に記載の方法により調製された処理沈殿シリカ。
- 請求項30に記載のプロセスにより製造された前記処理沈殿シリカを含むゴム組成物、ゴム物品、またはタイヤトレッド。
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