JP3563811B2 - Polyfluoroaralkylsilane derivative and method for producing the same - Google Patents

Polyfluoroaralkylsilane derivative and method for producing the same Download PDF

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Publication number
JP3563811B2
JP3563811B2 JP05169695A JP5169695A JP3563811B2 JP 3563811 B2 JP3563811 B2 JP 3563811B2 JP 05169695 A JP05169695 A JP 05169695A JP 5169695 A JP5169695 A JP 5169695A JP 3563811 B2 JP3563811 B2 JP 3563811B2
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Japan
Prior art keywords
general formula
polyfluoroaralkylsilane
derivative
same
producing
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JP05169695A
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Japanese (ja)
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JPH08311082A (en
Inventor
猛雄 小中原
高広 清洲
孝志 門出
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Neos Co Ltd
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Neos Co Ltd
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    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts

Description

【０００１】
【産業上の利用分野】
本発明は、耐熱性、撥水性、および絶縁性だけでなく、耐油性、耐低温性、および耐溶剤性にも優れたシリコーン製品の原料として、また高速液体クロマトグラフィー用充填剤の原料として有用な含フッ素シリコン化合物に関する。
【０００２】
【従来の技術】
ポリフルオロアラルキル型のシラン化合物は他に知られていない。
【０００３】
【発明が解決しようとする課題】
本発明は、安定なポリフルオロアラルキルシラン誘導体を提供するためになされたものであり、耐熱性、撥水性、絶縁性、耐油性、耐低温性、および耐溶剤性に優れたシリコーン原料、更に高速液体クロマトグラフィー用充填剤の原料として有用である。
【０００４】
【課題を解決するための手段】
即ち本発明は、一般式（１）：
【０００５】
【化４】

Figure 0003563811
（式中、Ｘ１、Ｘ２、およびＸ３は、ハロゲン原子、炭素原子数１〜５のアルキル基、および炭素原子数１〜５のアルコキシ基を示し、同時に同じであってもよい）で表されるポリフルオロアラルキルシラン誘導体に関する。
【０００６】
一般式（１）において、Ｘ１、Ｘ２、およびＸ３は、ハロゲン原子、好ましくは塩素原子、炭素原子数１〜５のアルキル基、好ましくはメチル基、またはエチル基、および炭素数１〜５のアルコキシ基、好ましくはメトキシ基、またはエトキシ基を示し、Ｘ１、Ｘ２、およびＸ３は、同時に同じであってもよい。
【０００７】
一般式（１）で表されるポリフルオロアラルキルシラン誘導体の製造方法として特に好適な方法は、一般式（２）：
【０００８】
【化５】
Figure 0003563811
で表されるポリフルオロアルキルスチレンと、一般式（３）：
【０００９】
【化６】
Figure 0003563811
（式中、Ｘ１、Ｘ２、およびＸ３は、一般式（１）と同意義である。）で表されるシラン誘導体を、常圧もしくは加圧下において、白金触媒を用いて反応させる方法である。
【００１０】
一般式（３）の物質としては、ＨＳｉＣｌ３、ＨＳｉ（ＯＣＨ３）３、ＨＳｉ（ＯＣＨ２ＣＨ３）３、ＨＳｉ（ＣＨ３）Ｃｌ２、ＨＳｉ（ＣＨ３）２Ｃｌ等が例示される。
【００１１】
反応原料として使用する上記のポリフルオロアルキルスチレンは、例えば公開特許公報・平３−７４３４０にあるように次の反応によって調製される。
【００１２】
【化７】
Figure 0003563811
【００１３】
触媒として使用される白金触媒の例としては、白金ージビニルテトラメチルジシロキサン錯体、Ｈ２ＰｔＣｌ６・６Ｈ２Ｏ、Ｐｔ−Ｃ（５％Ｐｔ）等が挙げられる。好ましくは、白金ージビニルテトラメチルジシロキサン錯体である。使用量は、一般的にスチレンに対してモル比で１，０００分の１から１，０００，０００分の１であり、好ましくは、１０，０００分の１から１００，０００分の１である。
【００１４】
反応温度は、一般に常温以上で行われるが、６０℃〜１００℃が好ましい。
【００１５】
【実施例】
以下、本発明を実施例によって説明する。
実施例
窒素導入管、冷却管、温度計、および攪拌機を備えた、充分に乾燥させたフラスコ（１００ｍＬ）に、一般式（２）ポリフルオロアルキルスチレン（ｐ−， ｍ−混合物）４２．３２ｇ（０．０９７ｍｏｌ）、クロロジメチルシラン１２．３５ｇ（０．１３１ｍｏｌ）、および白金−ジビニルテトラメチルジシロキサン錯体キシレン溶液（Ｐｔとして０．３６２重量％）３．５２ｇを入れ、８０℃で３時間加熱反応させた。その後、減圧蒸留によって精製し、一般式（４）で表されるポリフルオロアラルキルシラン２２．０４ｇ（０．０４１５ｍｏｌ）の無色透明液体を得た。（収率：４３％）
【００１６】
【化８】
Figure 0003563811
【００１７】
ＮＭＲとＩＲの測定値を表．１に示した。
【００１８】
【表１】
Figure 0003563811
【００１９】
【発明の効果】
本発明によって提供される新規なポリフルオロアラルキルシラン誘導体は、安定であり、且つ耐熱性、撥水性、および絶縁性だけでなく、耐油性、耐低温性、および耐溶剤性にも優れたシリコーン製品の原料や高速液体コロマトグラフィー用充填剤の原料として有用なものである。[0001]
[Industrial applications]
INDUSTRIAL APPLICABILITY The present invention is useful as a raw material of a silicone product excellent not only in heat resistance, water repellency, and insulating properties but also in oil resistance, low temperature resistance, and solvent resistance, and as a raw material of a filler for high performance liquid chromatography. A fluorine-containing silicon compound.
[0002]
[Prior art]
No other polyfluoroaralkyl-type silane compounds are known.
[0003]
[Problems to be solved by the invention]
The present invention has been made to provide a stable polyfluoroaralkylsilane derivative, and is a silicone raw material having excellent heat resistance, water repellency, insulation, oil resistance, low temperature resistance, and solvent resistance. It is useful as a raw material for a packing material for liquid chromatography.
[0004]
[Means for Solving the Problems]
That is, the present invention provides a compound represented by the general formula (1):
[0005]
Embedded image
Figure 0003563811
(Wherein X 1 , X 2 , and X 3 represent a halogen atom, an alkyl group having 1 to 5 carbon atoms, and an alkoxy group having 1 to 5 carbon atoms, and may be the same at the same time) It relates to the represented polyfluoroaralkylsilane derivative.
[0006]
In the general formula (1), X 1 , X 2 , and X 3 each represent a halogen atom, preferably a chlorine atom, an alkyl group having 1 to 5 carbon atoms, preferably a methyl group or an ethyl group, and 1 to 3 carbon atoms. 5 represents an alkoxy group, preferably a methoxy group or an ethoxy group, and X 1 , X 2 and X 3 may be the same at the same time.
[0007]
A particularly suitable method for producing the polyfluoroaralkylsilane derivative represented by the general formula (1) is the general formula (2):
[0008]
Embedded image
Figure 0003563811
And a polyfluoroalkylstyrene represented by the following general formula (3):
[0009]
Embedded image
Figure 0003563811
(Wherein X 1 , X 2 , and X 3 have the same meanings as in the general formula (1).) A method in which a silane derivative represented by the following formula is reacted at normal pressure or under pressure using a platinum catalyst. It is.
[0010]
Examples of the substance of the general formula (3) include HSiCl 3 , HSi (OCH 3 ) 3 , HSi (OCH 2 CH 3 ) 3 , HSi (CH 3 ) Cl 2 , and HSi (CH 3 ) 2 Cl.
[0011]
The above-mentioned polyfluoroalkylstyrene used as a reaction raw material is prepared by the following reaction, for example, as disclosed in JP-A-3-74340.
[0012]
Embedded image
Figure 0003563811
[0013]
Examples of the platinum catalyst used as the catalyst, platinum over divinyltetramethyldisiloxane complex, H 2 PtCl 6 · 6H 2 O, Pt-C (5% Pt) and the like. Preferably, it is a platinum divinyltetramethyldisiloxane complex. The amount used is generally from 1 / 1,000 to 1 / 100,000, preferably from 1 / 1,000 to 1 / 100,000 in molar ratio to styrene. .
[0014]
The reaction is generally carried out at a normal temperature or higher, but preferably 60 ° C to 100 ° C.
[0015]
【Example】
Hereinafter, the present invention will be described with reference to examples.
EXAMPLE In a thoroughly dried flask (100 mL) equipped with a nitrogen inlet tube, a condenser tube, a thermometer, and a stirrer, 42.32 g of a polyfluoroalkylstyrene (p-, m-mixture) of the general formula (2) ( 0.097 mol), 12.35 g (0.131 mol) of chlorodimethylsilane, and 3.52 g of a platinum-divinyltetramethyldisiloxane complex xylene solution (0.362% by weight as Pt), and heated at 80 ° C. for 3 hours. I let it. Thereafter, purification was performed by distillation under reduced pressure to obtain 22.04 g (0.0415 mol) of a colorless transparent liquid of polyfluoroaralkylsilane represented by the general formula (4). (Yield: 43%)
[0016]
Embedded image
Figure 0003563811
[0017]
Table showing measured values of NMR and IR. 1 is shown.
[0018]
[Table 1]
Figure 0003563811
[0019]
【The invention's effect】
The novel polyfluoroaralkylsilane derivative provided by the present invention is a silicone product that is stable and has excellent heat resistance, water repellency, and insulation as well as oil resistance, low temperature resistance, and solvent resistance. And useful as a raw material for high-performance liquid chromatography.

Claims (2)

一般式（１）：
Figure 0003563811
（式中、Ｘ１、Ｘ２、およびＸ３は、ハロゲン原子、炭素原子数１〜５のアルキル基、および炭素原子数１〜５のアルコキシ基を示し、同時に同じであってもよい。）で表されるポリフルオロアラルキルシラン誘導体。General formula (1):
Figure 0003563811
 (In the formula, X 1 , X 2 , and X 3 represent a halogen atom, an alkyl group having 1 to 5 carbon atoms, and an alkoxy group having 1 to 5 carbon atoms, and may be the same at the same time.) A polyfluoroaralkylsilane derivative represented by the formula: 一般式（２）：
Figure 0003563811
で表されるポリフルオロアルキルスチレンと、一般式（３）：
Figure 0003563811
［式中、Ｘ１、Ｘ２、およびＸ３は、一般式（１）の場合と同意義である］で表されるシラン誘導体とを、白金触媒を用いて反応させることを特徴とする請求項１記載のポリフルオロアラルキルシラン誘導体の製造方法。General formula (2):
Figure 0003563811
 And a polyfluoroalkylstyrene represented by the following general formula (3):
Figure 0003563811
 Wherein X 1 , X 2 and X 3 have the same meanings as in the case of the general formula (1), and are reacted with a platinum catalyst. Item 10. A method for producing a polyfluoroaralkylsilane derivative according to Item 1.
JP05169695A 1995-02-15 1995-02-15 Polyfluoroaralkylsilane derivative and method for producing the same Expired - Fee Related JP3563811B2 (en)

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US7816435B2 (en) * 2007-10-31 2010-10-19 Momentive Performance Materials Inc. Halo-functional silane, process for its preparation, rubber composition containing same and articles manufactured therefrom
JP2011184304A (en) * 2010-03-04 2011-09-22 Tokyo Univ Of Science Silane coupling agent and method for producing the same

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