JPH08311082A - Polyfluoroaralkylsilane derivative and its production - Google Patents
Polyfluoroaralkylsilane derivative and its productionInfo
- Publication number
- JPH08311082A JPH08311082A JP7051696A JP5169695A JPH08311082A JP H08311082 A JPH08311082 A JP H08311082A JP 7051696 A JP7051696 A JP 7051696A JP 5169695 A JP5169695 A JP 5169695A JP H08311082 A JPH08311082 A JP H08311082A
- Authority
- JP
- Japan
- Prior art keywords
- derivative
- resistance
- polyfluoroaralkylsilane
- raw material
- general formula
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims abstract description 13
- 229910052697 platinum Inorganic materials 0.000 claims abstract description 7
- 239000003054 catalyst Substances 0.000 claims abstract description 6
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 4
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 4
- 150000004756 silanes Chemical class 0.000 claims abstract description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 239000002994 raw material Substances 0.000 abstract description 9
- 239000002904 solvent Substances 0.000 abstract description 5
- 239000000126 substance Substances 0.000 abstract description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 5
- DSVRVHYFPPQFTI-UHFFFAOYSA-N bis(ethenyl)-methyl-trimethylsilyloxysilane;platinum Chemical compound [Pt].C[Si](C)(C)O[Si](C)(C=C)C=C DSVRVHYFPPQFTI-UHFFFAOYSA-N 0.000 abstract description 4
- 150000001875 compounds Chemical class 0.000 abstract description 3
- 239000000945 filler Substances 0.000 abstract description 3
- 238000004128 high performance liquid chromatography Methods 0.000 abstract description 3
- 229920001296 polysiloxane Polymers 0.000 abstract description 3
- YGHUUVGIRWMJGE-UHFFFAOYSA-N chlorodimethylsilane Chemical compound C[SiH](C)Cl YGHUUVGIRWMJGE-UHFFFAOYSA-N 0.000 abstract description 2
- 238000005292 vacuum distillation Methods 0.000 abstract description 2
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 238000009413 insulation Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229940024463 silicone emollient and protective product Drugs 0.000 description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- -1 silane compound Chemical class 0.000 description 1
- 150000003377 silicon compounds Chemical class 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- 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
Landscapes
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Description
【０００１】[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。FIELD OF THE INVENTION The present invention is used as a raw material for silicone products which are excellent not only in heat resistance, water repellency and insulation but also in oil resistance, low temperature resistance and solvent resistance, and also in high performance liquid chromatography. The present invention relates to a fluorine-containing silicon compound that is useful as a raw material for fillers for automobiles.
【０００２】[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。2. Description of the Related Art No other polyfluoroaralkyl type silane compound is known.
【０００３】[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。The present invention has been made in order to provide a stable polyfluoroaralkylsilane derivative, and has heat resistance, water repellency, insulation, oil resistance, low temperature resistance, and solvent resistance. It is useful as a silicone raw material having excellent properties and as a raw material for a packing material for high performance liquid chromatography.
【０００４】[0004]
【課題を解決するための手段】即ち本発明は、一般式
（１）：That is, the present invention provides a compound represented by the general formula (1):
【０００５】[0005]
【化４】 （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。[Chemical 4] (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) It relates to a represented polyfluoroaralkylsilane derivative.
【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。In the general formula (1), X 1 , X 2 and X 3 are 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 a carbon atom. It represents an alkoxy group of the formulas 1 to 5, 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】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）：A particularly preferred method for producing the polyfluoroaralkylsilane derivative represented by the general formula (1) is represented by the general formula (2):
【０００８】[0008]
【化５】 で表されるポリフルオロアルキルスチレンと、一般式
（３）：Embedded image And a polyfluoroalkylstyrene represented by the general formula (3):
【０００９】[0009]
【化６】 （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。[Chemical 6] (In the formula, X 1 , X 2 , and X 3 have the same meaning as in the general formula (1).) A method of reacting a silane derivative represented by the general formula (1) with a platinum catalyst under normal pressure or pressure. Is.
【００１０】一般式（３）の物質としては、ＨＳiＣ
ｌ3、ＨＳi（ＯＣＨ3）3、ＨＳi（ＯＣＨ2ＣＨ3）3、Ｈ
Ｓi（ＣＨ3）Ｃｌ2、ＨＳi（ＣＨ3）2Ｃｌ等が例示され
る。As the substance of the general formula (3), HSiC
l 3 , HSi (OCH 3 ) 3 , HSi (OCH 2 CH 3 ) 3 , H
Examples are Si (CH 3 ) Cl 2 and HSi (CH 3 ) 2 Cl.
【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３−７
４３４０にあるように次の反応によって調製される。The above-mentioned polyfluoroalkylstyrene used as a reaction raw material is disclosed in, for example, Japanese Patent Laid-Open Publication No. 3-7.
Prepared by the following reaction as in 4340.
【００１２】[0012]
【化７】 [Chemical 7]
【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、Ｈ2
ＰtＣｌ6・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。Examples of platinum catalysts used as catalysts are platinum-divinyltetramethyldisiloxane complex, H 2
PtCl 6 · 6H 2 O, Pt -C (5% Pt) and the like.
Preferred is a platinum-divinyltetramethyldisiloxane complex. The amount used is generally from 1/1000 to 1,000,000 in molar ratio to styrene, preferably from 1 / 10,000 to 100,000.
It is one-third.
【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。The reaction temperature is generally room temperature or higher, preferably 60 ° C to 100 ° C.
【００１５】[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（0.131mo
l）、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%）EXAMPLES The present invention will be described below with reference to examples. Example equipped with a nitrogen introduction tube, a cooling tube, a thermometer, and a stirrer,
In a fully dried flask (100 mL), 42.32 g of general formula (2) polyfluoroalkylstyrene (p-, m-mixture)
(0.097mol), chlorodimethylsilane 12.35g (0.131mo
l), and 3.52 g of platinum-divinyltetramethyldisiloxane complex xylene solution (0.362 wt% as Pt),
The mixture was heated and reacted at 80 ° C. for 3 hours. Then, it was purified by vacuum distillation to obtain 22.04 g (0.0415 mol) of a colorless transparent liquid of polyfluoroaralkylsilane represented by the general formula (4). (Yield: 43%)
【００１６】[0016]
【化８】 Embedded image
【００１７】ＮＭＲとＩＲの測定値を表．１に示した。Table 1 shows the measured values of NMR and IR. Shown in 1.
【００１８】[0018]
【表１】 [Table 1]
【００１９】[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。INDUSTRIAL APPLICABILITY The novel polyfluoroaralkylsilane derivative provided by the present invention is stable and has not only heat resistance, water repellency and insulating property but also oil resistance, low temperature resistance and solvent resistance. It is also useful as a raw material for excellent silicone products and a filler for high-performance liquid coromatography.
───────────────────────────────────────────────────── フロントページの続き (51)Int.Cl.6 識別記号 庁内整理番号 ＦＩ 技術表示箇所 Ｃ０７Ｆ 7/14 Ｃ０７Ｆ 7/14 7/18 7/18 Ｅ // Ｃ０７Ｂ 61/00 ３００ Ｃ０７Ｂ 61/00 ３００ ─────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. 6 Identification code Office reference number FI Technical display location C07F 7/14 C07F 7/14 7/18 7/18 E // C07B 61/00 300 C07B 61 / 00 300
Claims (2)
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。1. General formula (1): (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.
（３）： 【化３】 ［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。2. General formula (2): And a polyfluoroalkylstyrene represented by the general formula (3): [Wherein, X 1 , X 2 , and X 3 have the same meanings as in the case of the general formula (1)] are reacted with a silane derivative using a platinum catalyst. Item 2. A method for producing a polyfluoroaralkylsilane derivative according to Item 1.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP05169695A JP3563811B2 (en) | 1995-02-15 | 1995-02-15 | Polyfluoroaralkylsilane derivative and method for producing the same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP05169695A JP3563811B2 (en) | 1995-02-15 | 1995-02-15 | Polyfluoroaralkylsilane derivative and method for producing the same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH08311082A true JPH08311082A (en) | 1996-11-26 |
| JP3563811B2 JP3563811B2 (en) | 2004-09-08 |
Family
ID=12894072
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP05169695A Expired - Fee Related JP3563811B2 (en) | 1995-02-15 | 1995-02-15 | Polyfluoroaralkylsilane derivative and method for producing the same |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP3563811B2 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2011502124A (en) * | 2007-10-31 | 2011-01-20 | モメンティブ パフォーマンス マテリアルズ インコーポレイテッド | Halofunctional silane, process for its preparation, rubber composition containing it, and products made therefrom |
| JP2011184304A (en) * | 2010-03-04 | 2011-09-22 | Tokyo Univ Of Science | Silane coupling agent and method for producing the same |
-
1995
- 1995-02-15 JP JP05169695A patent/JP3563811B2/en not_active Expired - Fee Related
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2011502124A (en) * | 2007-10-31 | 2011-01-20 | モメンティブ パフォーマンス マテリアルズ インコーポレイテッド | Halofunctional silane, process for its preparation, rubber composition containing it, and products made therefrom |
| JP2011184304A (en) * | 2010-03-04 | 2011-09-22 | Tokyo Univ Of Science | Silane coupling agent and method for producing the same |
Also Published As
| Publication number | Publication date |
|---|---|
| JP3563811B2 (en) | 2004-09-08 |
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