JPH1017579A - N,n-bis(trimethylsilyl)aminopropylsilane and its production - Google Patents
N,n-bis(trimethylsilyl)aminopropylsilane and its productionInfo
- Publication number
- JPH1017579A JPH1017579A JP19001196A JP19001196A JPH1017579A JP H1017579 A JPH1017579 A JP H1017579A JP 19001196 A JP19001196 A JP 19001196A JP 19001196 A JP19001196 A JP 19001196A JP H1017579 A JPH1017579 A JP H1017579A
- Authority
- JP
- Japan
- Prior art keywords
- trimethylsilyl
- bis
- compound
- aminopropyl
- reaction
- 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.)
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- Silicon Polymers (AREA)
Abstract
Description
【０００１】[0001]
【発明の属する技術分野】本発明は、アミノプロピル変
性シリコーンオイルの製造原料、シランカップリング
剤、表面処理剤、各種シランカップリング剤原料として
有用な新規なＮ，Ｎ−ビス（トリメチルシリル）アミノ
プロピルシラン化合物に関する。TECHNICAL FIELD The present invention relates to a novel N, N-bis (trimethylsilyl) aminopropyl useful as a raw material for producing aminopropyl-modified silicone oil, a silane coupling agent, a surface treatment agent and various silane coupling agent raw materials. It relates to a silane compound.
【０００２】[0002]
【従来の技術及び発明が解決しようとする課題】アミノ
プロピル変性シリコーンオイルは、アミノ基の吸着能力
を生かして繊維処理剤、つや出し剤、塗料添加剤、樹脂
改質用オイル等の用途で広く使用されている。この変性
オイルは、一般的にはアミノプロピルメチルジメトキシ
シラン又はアミノプロピルメチルジエトキシシランを加
水分解し、得られたオリゴマーとオクタメチルテトラシ
ロキサンなどの環状シロキサンとを塩基性触媒を使用し
て反応させることにより得られる。2. Description of the Related Art Aminopropyl-modified silicone oils are widely used in fiber treatment agents, polishing agents, paint additives, resin modifying oils, etc. by utilizing the ability to adsorb amino groups. Have been. This modified oil generally hydrolyzes aminopropylmethyldimethoxysilane or aminopropylmethyldiethoxysilane, and reacts the obtained oligomer with a cyclic siloxane such as octamethyltetrasiloxane using a basic catalyst. It can be obtained by:
【０００３】しかしながら、上記合成法では、原料のア
ミノプロピルシラン化合物が反応性が高い遊離のアミノ
基を有するため、オリゴマー化時及び環状シロキサンと
の反応時、アミノ基がケイ素に結合した種々の化合物が
副生してしまい、目的とするポリシロキサン骨格にアミ
ノプロピル基が結合した構造のポリマーを得ることが難
しいという問題があった。従って、目的とする構造のア
ミノプロピル変性シリコーンオイルを容易に得るための
新規合成原料の開発が望まれていた。However, in the above synthesis method, the starting aminopropylsilane compound has a highly reactive free amino group. Therefore, during the oligomerization and the reaction with the cyclic siloxane, various compounds in which the amino group is bonded to silicon are used. However, there is a problem that it is difficult to obtain a polymer having a structure in which an aminopropyl group is bonded to a target polysiloxane skeleton. Therefore, development of a new synthetic raw material for easily obtaining an aminopropyl-modified silicone oil having a desired structure has been desired.
【０００４】[0004]
【課題を解決するための手段及び発明の実施の形態】本
発明者は、上記事情に鑑み鋭意検討を重ねた結果、Ｎ，
Ｎ−ビス（トリメチルシリル）アリルアミンとメチルジ
アルコキシシランとを白金触媒の存在下に反応させるこ
とにより得られる、アミノプロピルシラン化合物のアミ
ノ基の水素原子をトリメチルシリル基で置換した下記一
般式（１）で示されるアミノプロピルシラン化合物が、
目的とするポリシロキサン骨格にアミノプロピル基が結
合した構造のアミノプロピル変性シリコーンオイルを容
易に得るための優れた合成原料であることを見出した。Means for Solving the Problems and Embodiments of the Invention The present inventor has conducted intensive studies in view of the above circumstances and found that N,
In the following general formula (1), an aminopropylsilane compound obtained by reacting N-bis (trimethylsilyl) allylamine with methyldialkoxysilane in the presence of a platinum catalyst, wherein a hydrogen atom of an amino group of the aminopropylsilane compound is substituted by a trimethylsilyl group. The aminopropylsilane compound shown is
It has been found that this is an excellent synthetic raw material for easily obtaining an aminopropyl-modified silicone oil having a structure in which an aminopropyl group is bonded to an intended polysiloxane skeleton.
【０００５】即ち、下記式（１）の化合物は、アミノ基
の２つの水素原子がいずれもトリメチルシリル基で置換
されているため、アミノ基としての反応性は抑えられて
おり、このＮ，Ｎ−ビス（トリメチルシリル）アミノ基
はケイ素と結合しない。また、トリメチルシリル基との
窒素との結合はアルカリ系では極めて安定であるが、中
性及び酸性系では、容易に分解して遊離のアミノ基を再
生できる。よって、本発明化合物を使用してアルカリ性
条件下に加水分解し、得られたオリゴマーと環状シロキ
サンを塩基性触媒を使用して反応させ、その後に中性又
は酸性下で脱トリメチルシリル化することにより、目的
とする構造のアミノプロピル変性シリコーンオイルが得
られることを知見し、本発明をなすに至ったものであ
る。That is, in the compound of the following formula (1), the reactivity as an amino group is suppressed because two hydrogen atoms of an amino group are both substituted by a trimethylsilyl group. Bis (trimethylsilyl) amino groups do not bind to silicon. The bond between nitrogen and the trimethylsilyl group is extremely stable in an alkaline system, but can be easily decomposed and regenerated to a free amino group in a neutral or acidic system. Therefore, the compound of the present invention is hydrolyzed under alkaline conditions, the obtained oligomer is reacted with the cyclic siloxane using a basic catalyst, and then subjected to detrimethylsilylation under neutral or acidic conditions. The present inventors have found that an aminopropyl-modified silicone oil having a desired structure can be obtained, and have accomplished the present invention.
【０００６】従って、本発明は、下記一般式（１）で示
されるＮ，Ｎ−ビス（トリメチルシリル）アミノプロピ
ルシラン化合物及びＮ，Ｎ−ビス（トリメチルシリル）
アリルアミンとメチルジアルコキシシランとを反応させ
ることからなる該化合物の製造方法を提供する。Accordingly, the present invention provides an N, N-bis (trimethylsilyl) aminopropylsilane compound represented by the following general formula (1) and an N, N-bis (trimethylsilyl) compound:
Provided is a method for producing the compound, comprising reacting allylamine with methyldialkoxysilane.
【０００７】[0007]
【化２】 （但し、式中Ｒはメチル基又はエチル基である。）Embedded image (Where R is a methyl group or an ethyl group.)
【０００８】以下、本発明につき更に詳細に説明する
と、本発明の化合物は、下記一般式（１）で示される
Ｎ，Ｎ−ビス（トリメチルシリル）アミノプロピルシラ
ン化合物である。Hereinafter, the present invention will be described in more detail. The compound of the present invention is an N, N-bis (trimethylsilyl) aminopropylsilane compound represented by the following general formula (1).
【０００９】[0009]
【化３】 （但し、式中Ｒはメチル基又はエチル基である。）Embedded image (Where R is a methyl group or an ethyl group.)
【００１０】上記式（１）の化合物は、アリルアミンと
トリメチルクロロシランとトリエチルアミンとをルイス
酸触媒の存在下に反応させる公知の方法（Ｐｈｏｓｐｈ
ｏｒｕｓ，Ｓｕｌｆｕｒ，ａｎｄ Ｓｉｌｉｃｏｎｅ
６８，２５（１９９２）等参照）で得られるＮ，Ｎ−ビ
ス（トリメチルシリル）アリルアミンと、メチルジメト
キシシラン、メチルジエトキシシラン等のメチルジアル
コキシシランとを塩化白金酸等の白金触媒の存在下に反
応させることにより得ることができる。The compound of the above formula (1) can be prepared by a known method (Phosph) by reacting allylamine, trimethylchlorosilane and triethylamine in the presence of a Lewis acid catalyst.
orus, Sulfur, and Silicone
68, 25 (1992), etc.) and methyl dialkoxysilane such as methyldimethoxysilane and methyldiethoxysilane in the presence of a platinum catalyst such as chloroplatinic acid. It can be obtained by reacting.
【００１１】この場合、Ｎ，Ｎ−ビス（トリメチルシリ
ル）アリルアミンとメチルジアルコキシシランの使用割
合は、Ｎ，Ｎ−ビス（トリメチルシリル）アリルアミン
１モルに対してメチルジアルコキシシランを０．１〜３
モル、特に１〜１．５モルの範囲で使用することが好ま
しい。In this case, the ratio of N, N-bis (trimethylsilyl) allylamine to methyldialkoxysilane is such that methyl dialkoxysilane is used in an amount of 0.1 to 3 per mole of N, N-bis (trimethylsilyl) allylamine.
It is preferable to use it in an amount of, particularly, 1 to 1.5 mol.
【００１２】また、反応に使用される白金触媒の量は、
０．１〜１０００ｐｐｍ、特に５〜５００ｐｐｍが好ま
しい。The amount of the platinum catalyst used in the reaction is as follows:
0.1-1000 ppm, especially 5-500 ppm is preferred.
【００１３】なお、反応条件は適宜調整できるが、０〜
２００℃、特に５０〜１５０℃で０．５〜２０時間反応
させることが好ましい。The reaction conditions can be appropriately adjusted.
The reaction is preferably performed at 200 ° C., particularly 50 to 150 ° C. for 0.5 to 20 hours.
【００１４】[0014]
【発明の効果】本発明の上記式（１）のＮ，Ｎ−ビス
（トリメチルシリル）アミノプロピルシラン化合物は、
これを原料として使用した場合、副生物なく目的とする
ポリシロキサン骨格にアミノプロピル基が結合した構造
のアミノプロピル変性シリコーンオイルを容易に得るこ
とができる。According to the present invention, the N, N-bis (trimethylsilyl) aminopropylsilane compound of the above formula (1) is
When this is used as a raw material, an aminopropyl-modified silicone oil having a structure in which an aminopropyl group is bonded to a target polysiloxane skeleton can be easily obtained without by-products.
【００１５】また、本発明の上記式（１）の化合物は、
シランカップリング剤、表面処理剤としても有用であ
る。The compound of the above formula (1) of the present invention is
It is also useful as a silane coupling agent and a surface treatment agent.
【００１６】更に、本発明の化合物は、メタノール又は
エタノールと反応させることにより、容易に汎用シラン
カップリング剤である３−アミノプロピルメチルジメト
キシシラン、３−アミノプロピルメチルジエトキシシラ
ンに変換できるため、その合成中間体としても有用であ
る。Furthermore, the compound of the present invention can be easily converted to 3-aminopropylmethyldimethoxysilane and 3-aminopropylmethyldiethoxysilane, which are general-purpose silane coupling agents, by reacting with methanol or ethanol. It is also useful as a synthetic intermediate.
【００１７】[0017]
【実施例】以下、合成例及び実施例を示して本発明を具
体的に説明するが、本発明は下記実施例に制限されるも
のではない。なお、各例中の部はいずれも重量部であ
る。EXAMPLES The present invention will be specifically described below with reference to Synthesis Examples and Examples, but the present invention is not limited to the following Examples. All parts in each example are parts by weight.
【００１８】〔合成例〕撹拌機、還流冷却器、温度計及
び滴下ロートを備えた２リットルのガラスフラスコ中に
トリメチルクロロシラン３２５．９ｇ（３．０ｍｌ）、
トルエン６００ｍｌ及び触媒として塩化アルミニウム１
０．０ｇ（７５ｍｍｏｌ）を仕込み、そこに滴下ロート
よりアリルアミン８５．７ｇ（１．５ｍｏｌ）及びトリ
エチルアミン３３３．９ｇ（３．３ｍｏｌ）を内温５０
〜６０℃に保ちながら３時間で滴下し、そのまま６時間
熟成した。この反応液へ水酸化ナトリウム水を加えて生
成したトリエチルアミン塩酸塩を溶解した後、有機層を
分離し、減圧蒸留により９０〜９１℃／４０ｍｍＨｇの
留分を分取したところ、Ｎ，Ｎ−ビス（トリメチルシリ
ル）アリルアミン２４２．４ｇが得られた。[Synthesis Example] In a 2 liter glass flask equipped with a stirrer, a reflux condenser, a thermometer and a dropping funnel, 325.9 g (3.0 ml) of trimethylchlorosilane was added.
600 ml of toluene and aluminum chloride 1 as catalyst
0.0 g (75 mmol) was charged, and 85.7 g (1.5 mol) of allylamine and 333.9 g (3.3 mol) of triethylamine were added thereto from the dropping funnel at an internal temperature of 50.
The solution was added dropwise over 3 hours while maintaining the temperature at 滴下 60 ° C., and the mixture was aged for 6 hours. An aqueous sodium hydroxide solution was added to the reaction solution to dissolve the triethylamine hydrochloride formed. The organic layer was separated, and a fraction of 90 to 91 ° C./40 mmHg was collected by distillation under reduced pressure. 242.4 g of (trimethylsilyl) allylamine were obtained.
【００１９】〔実施例１〕撹拌機、還流冷却器、温度計
及び滴下ロートを備えた５００ｍｌのガラスフラスコ中
に上記合成例で得られたＮ，Ｎ−ビス（トリメチルシリ
ル）アリルアミン１００．８ｇ（０．５ｍｏｌ）及びＨ
2ＰｔＣｌ6・６Ｈ2Ｏの４％イソプロピルアルコール溶
液０．４９ｇを仕込み、これに滴下ロートよりメチルジ
メトキシシラン５３．１ｇ（０．５ｍｏｌ）を７０〜８
０℃にて３時間かけて滴下し、そのまま２時間熟成し
た。得られた反応液から減圧蒸留により９１〜９３℃／
３ｍｍＨｇの留分１４２．０ｇを分取した。Example 1 In a 500 ml glass flask equipped with a stirrer, reflux condenser, thermometer and dropping funnel, 100.8 g of N, N-bis (trimethylsilyl) allylamine (0. .5 mol) and H
G of 4% isopropyl alcohol solution 0.49g of 2 PtCl 6 · 6H 2 O, this methyldimethoxysilane 53.1g from the dropping funnel (0.5 mol) 70 to 8
The solution was added dropwise at 0 ° C. over 3 hours and aged for 2 hours. From the obtained reaction solution, 91-93 ° C /
142.0 g of a 3 mmHg fraction was collected.
【００２０】得られた化合物の質量スペクトル、核磁気
共鳴スペクトル（ＮＭＲ）及び赤外吸収スペクトルの測
定結果を以下に示す。 質量スペクトル（ＥＩ法）：ｍ／ｚ（帰属） ３０７（分子イオン（Ｍ+）ピーク） 赤外吸収スペクトル 図１のチャート参照1 Ｈ及び13Ｃ核磁気共鳴スペクトル（ＣＤＣｌ3中）The measurement results of the mass spectrum, nuclear magnetic resonance spectrum (NMR) and infrared absorption spectrum of the obtained compound are shown below. Mass spectrum (EI method): m / z (assignment) 307 (molecular ion (M + ) peak) Infrared absorption spectrum See chart of FIG. 1 1 H and 13 C nuclear magnetic resonance spectra (in CDCl 3 )
【００２１】[0021]
【化４】 Embedded image
【００２２】[0022]
【表１】 [Table 1]
【００２３】これらの結果より、得られた化合物がＮ，
Ｎ−ビス（トリメチルシリル）アミノプロピルメチルジ
メトキシシランであることが確認された。収率は９３％
であった。From these results, the obtained compound was N,
It was confirmed to be N-bis (trimethylsilyl) aminopropylmethyldimethoxysilane. 93% yield
Met.
【００２４】〔実施例２〕メチルジメトキシシラン５
３．１ｇ（０．５ｍｏｌ）をメチルジエトキシシラン６
７．２ｇ（０．５ｍｏｌ）に変更した以外は、実施例１
と同様にして反応を行った。得られた反応液から減圧蒸
留により９０〜９２℃／０．３ｍｍＨｇの留分１５２．
８ｇを分取した。Example 2 Methyldimethoxysilane 5
3.1 g (0.5 mol) of methyldiethoxysilane 6
Example 1 except that the amount was changed to 7.2 g (0.5 mol).
The reaction was carried out in the same manner as in. A fraction of 90 to 92 ° C./0.3 mmHg is obtained from the obtained reaction solution by distillation under reduced pressure.
8 g were dispensed.
【００２５】得られた化合物の質量スペクトル、核磁気
共鳴スペクトル（ＮＭＲ）及び赤外吸収スペクトルの測
定結果を以下に示す。 質量スペクトル（ＥＩ法）：ｍ／ｚ（帰属） ３３５（分子イオン（Ｍ+）ピーク） 赤外吸収スペクトル 図２のチャート参照1 Ｈ及び13Ｃ核磁気共鳴スペクトル（ＣＤＣｌ3中）The measurement results of the mass spectrum, nuclear magnetic resonance spectrum (NMR) and infrared absorption spectrum of the obtained compound are shown below. Mass spectrum (EI method): m / z (assignment) 335 (molecular ion (M + ) peak) Infrared absorption spectrum See chart of FIG. 2 1 H and 13 C nuclear magnetic resonance spectra (in CDCl 3 )
【００２６】[0026]
【化５】 Embedded image
【００２７】[0027]
【表２】 [Table 2]
【００２８】これらの結果より、得られた化合物がＮ，
Ｎ−ビス（トリメチルシリル）アミノプロピルメチルジ
エトキシシランであることが確認された。収率は９１％
であった。From these results, the obtained compound was N,
It was confirmed to be N-bis (trimethylsilyl) aminopropylmethyldiethoxysilane. 91% yield
Met.
【図面の簡単な説明】[Brief description of the drawings]
【図１】実施例１で得られた化合物の赤外吸収スペクト
ルのチャートである。FIG. 1 is a chart of an infrared absorption spectrum of a compound obtained in Example 1.
【図２】実施例２で得られた化合物の赤外吸収スペクト
ルのチャートである。FIG. 2 is a chart of an infrared absorption spectrum of the compound obtained in Example 2.
Claims (2)
ス（トリメチルシリル）アミノプロピルシラン化合物。 【化１】 （但し、式中Ｒはメチル基又はエチル基である。）1. An N, N-bis (trimethylsilyl) aminopropylsilane compound represented by the following general formula (1). Embedded image (Where R is a methyl group or an ethyl group.)
ルアミンとメチルジアルコキシシランとを反応させるこ
とを特徴とする請求項１記載のＮ，Ｎ−ビス（トリメチ
ルシリル）アミノプロピルシラン化合物の製造方法。2. The method for producing an N, N-bis (trimethylsilyl) aminopropylsilane compound according to claim 1, wherein N, N-bis (trimethylsilyl) allylamine is reacted with methyldialkoxysilane.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP19001196A JP3414134B2 (en) | 1996-07-01 | 1996-07-01 | N, N-bis (trimethylsilyl) aminopropylsilane compound and method for producing the same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP19001196A JP3414134B2 (en) | 1996-07-01 | 1996-07-01 | N, N-bis (trimethylsilyl) aminopropylsilane compound and method for producing the same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH1017579A true JPH1017579A (en) | 1998-01-20 |
| JP3414134B2 JP3414134B2 (en) | 2003-06-09 |
Family
ID=16250895
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP19001196A Expired - Lifetime JP3414134B2 (en) | 1996-07-01 | 1996-07-01 | N, N-bis (trimethylsilyl) aminopropylsilane compound and method for producing the same |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP3414134B2 (en) |
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| EP1481980A1 (en) * | 2003-05-30 | 2004-12-01 | Shin-Etsu Chemical Co., Ltd. | Bis(trimethylsilyl)aminopropyl substituted chlorosilanes |
| JP2006347917A (en) * | 2005-06-14 | 2006-12-28 | Shin Etsu Chem Co Ltd | Basket-form oligosiloxane having triorganosilylamino group |
| JP2009249312A (en) * | 2008-04-03 | 2009-10-29 | Hitachi Chem Co Ltd | Silane compound |
| JP2009249455A (en) * | 2008-04-03 | 2009-10-29 | Hitachi Chem Co Ltd | Epoxy resin molding material for sealing and electronic parts device |
| JP2011162496A (en) * | 2010-02-12 | 2011-08-25 | Shin-Etsu Chemical Co Ltd | Organic silicon compound having amino group protected with silyl group and method for producing the same |
| JP2013184945A (en) * | 2012-03-09 | 2013-09-19 | National Institute Of Advanced Industrial Science & Technology | Iminophosphorane compound, process for producing the same, and method of modifying surface of base material using the same |
| JP2015007003A (en) * | 2013-06-25 | 2015-01-15 | 信越化学工業株式会社 | Sulfur-containing organoxysilane compound having bissilylamino group and method of producing the same |
| JP2015091763A (en) * | 2013-11-08 | 2015-05-14 | 信越化学工業株式会社 | Organoxysilane compound having bis-silylamino group and production method thereof |
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