JPH10139784A - Production of vinylsilyl group-containing silicone compound - Google Patents

Production of vinylsilyl group-containing silicone compound

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Publication number
JPH10139784A
JPH10139784A JP29363996A JP29363996A JPH10139784A JP H10139784 A JPH10139784 A JP H10139784A JP 29363996 A JP29363996 A JP 29363996A JP 29363996 A JP29363996 A JP 29363996A JP H10139784 A JPH10139784 A JP H10139784A
Authority
JP
Japan
Prior art keywords
group
silicon compound
thf
vinyl
vinyl group
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.)
Pending
Application number
JP29363996A
Other languages
Japanese (ja)
Inventor
Takanao Iwahara
孝尚 岩原
Manabu Tsumura
学 津村
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Kanegafuchi Chemical Industry Co Ltd
Original Assignee
Kanegafuchi Chemical Industry Co Ltd
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Kanegafuchi Chemical Industry Co Ltd filed Critical Kanegafuchi Chemical Industry Co Ltd
Priority to JP29363996A priority Critical patent/JPH10139784A/en
Publication of JPH10139784A publication Critical patent/JPH10139784A/en
Pending legal-status Critical Current

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Abstract

PROBLEM TO BE SOLVED: To obtain the subject compound useful as a graft-modified component for organic polymers, a component for addition polymerization, etc., in a good yield by reacting a silicon compound having a silanol group or hydrolyzable group with a vinyl group-containing organic metal reagent. SOLUTION: When a silicon compound having a silanol group or hydrolyzable group X (e.g. dimethyldichlorosilane) is reacted with a vinyl group-containing organometallic reagent (e.g. vinylmagnesium chloride), the silicon compound having silanol group or a hydrolyzable group X and THF are charged into a flask and THF solution of the vinyl group-containing organometallic reagent is gradually dropped from a dropping funnel equipped with a pressure equalizer into the flask and reaction of these components is carried out by heating reaction mixture under reflux of THF for 2hr to readily provide the objective vinyl group-containing silicon compound useful as a graft-modified component for organic polymers, a component, etc., for vinyl polymerization or hydrosilylation polymerization in good yield.

Description

【発明の詳細な説明】DETAILED DESCRIPTION OF THE INVENTION

【０００１】[0001]

【発明の属する技術分野】本発明は、ビニルシリル基含
有ケイ素化合物の製造に関する。The present invention relates to the production of a vinylsilyl group-containing silicon compound.

【０００２】[0002]

【発明が解決しようとする課題】本発明により、有機重
合体のグラフト変性成分や、ビニル重合・ヒドロシリル
化重合の成分として有用なビニルシリル基含有ケイ素化
合物を容易に好収率で得ることができる。According to the present invention, a vinylsilyl group-containing silicon compound useful as a graft-modifying component for an organic polymer or a component for vinyl polymerization or hydrosilylation polymerization can be easily obtained in good yield.

【０００３】[0003]

【課題を解決するための手段】本発明は、シラノール基
または加水分解性基Ｘを有するケイ素化合物（１）とビ
ニル基含有有機金属試薬（２）とを反応させて、もとの
ケイ素化合物のＸの部分にビニル基ＣＨ＝ＣＨ2を導入
しビニル基含有ケイ素化合物（３）を製造する方法に関
する。According to the present invention, a silicon compound (1) having a silanol group or a hydrolyzable group X is reacted with a vinyl group-containing organometallic reagent (2) to obtain the original silicon compound. The present invention relates to a method for producing a vinyl group-containing silicon compound (3) by introducing a vinyl group CH ＝ CH 2 into a portion X.

【０００４】本発明で使用することのできるシラノール
基または加水分解性基Ｘを有するケイ素化合物は特に制
限なく使用することができる。ケイ素原子を１個有する
該化合物としてはＲnＳｉＸ4-n（Ｒは炭素数２０以下の
有機基、Ｘはシラノール基または加水分解性基、ｎは０
−３から選ばれる整数）で表される化合物をあげること
ができる。具体的な化合物を以下に例示する。ＳｉＣｌ
4、ＭｅＳｉＣｌ3、ＭｅＨＳｉＣｌ2、Ｍｅ2ＳｉＣ
ｌ2、Ｍｅ3ＳｉＣｌ、ＥｔＭｅＳｉＣｌ2、ＰｈＭｅＳ
ｉＣｌ2、Ｍｅ2ＨＳｉＣｌ、ＰｈＳｉＣｌ3、Ｓｉ（Ｏ
Ｍｅ）4、ＭｅＳｉ（ＯＭｅ）3、ＭｅＨＳｉ（ＯＭｅ）
2、Ｍｅ2Ｓｉ（ＯＭｅ）2、Ｍｅ3ＳｉＯＭｅ、ＥｔＭｅ
Ｓｉ（ＯＭｅ）2、Ｍｅ2ＨＳｉ（ＯＭｅ）、ＰｈＭｅＳ
ｉ（ＯＭｅ）2、ＰｈＳｉ（ＯＭｅ）3、ＰｈＭｅＳｉ
（ＯＭｅ）2、Ｓｉ（ＯＥｔ）4、ＭｅＳｉ（ＯＥ
ｔ）3、ＭｅＨＳｉ（ＯＥｔ）2、Ｍｅ2Ｓｉ（ＯＥ
ｔ）2、Ｍｅ3ＳｉＯＭｅ、ＥｔＭｅＳｉ（ＯＭｅ）2、
ＭｅＨＳｉ（ＯＥｔ）、ＭｅＳｉ（Ｏｉ-Ｐｒ）3、Ｍｅ
2Ｓｉ（Ｏｉ-Ｐｒ）2、ＰｈＭｅＳｉ（Ｏｉ-Ｐｒ）2、
ＭｅＳｉ（ＯＣ＝ＯＣＨ3）3、Ｍｅ2Ｓｉ（ＯＣ＝ＯＣ
Ｈ3）2、ＰｈＭｅＳｉ（ＯＣ＝ＯＣＨ3）2、ＭｅＳｉ
（Ｏ（Ｃ＝ＣＨ2）ＣＨ3）3、Ｍｅ2Ｓｉ（Ｏ（Ｃ＝ＣＨ
2）ＣＨ3）2、ＰｈＭｅＳｉ（Ｏ（Ｃ＝ＣＨ2）Ｃ
Ｈ3）2、ＭｅＳｉ（ＯＮ＝ＣＭｅ2）3、Ｍｅ2Ｓｉ（Ｏ
Ｎ＝ＣＭｅ2）2、ＰｈＭｅＳｉ（ＯＮ＝ＣＭｅ2）2、Ｍ
ｅＳｉ（Ｎ（Ｅｔ）（Ｃ＝Ｏ）ＣＨ3）3、Ｍｅ2Ｓｉ
（Ｎ（Ｅｔ）（Ｃ＝Ｏ）ＣＨ3）2、ＰｈＭｅＳｉ（Ｎ
（Ｅｔ）（Ｃ＝Ｏ）ＣＨ3）2、またケイ素原子を２個以
上有するケイ素化合物の具体例としては以下の化合物を
あげることができる。 ＣｌＳｉ（Ｍｅ）2ＯＳｉ（Ｍｅ）2Ｃｌ ＣｌＳｉ（Ｍｅ）2（ｐ-Ｐｈ）Ｓｉ（Ｍｅ）2Ｃｌ ＣｌＳｉ（Ｍｅ）2ＯＳｉ（Ｍｅ）2ＯＳｉ（Ｍｅ）2Ｃ
ｌ （（Ｃｌ）（Ｍｅ）2Ｓｉ）3Ｐｈ 本発明において通常使用することのできるビニル基含有
有機金属試薬としては、ビニルマグネシウムクロライド
ＴＨＦ溶液、ビニルマグネシウムブロマイドＴＨＦ溶
液、ビニルマグネシウムクロライドジエチルエーテル溶
液、ビニルマグネシウムブロマイドジエチルエーテル溶
液などをあげることができる。ビニルマグネシウムクロ
ライドＴＨＦ溶液は、マグネシウムとＴＨＦの混合物中
に塩化ビニルを導入して調製することができる。ＢｒＣ
Ｈ2ＣＨ2ＢｒやＣＨ3Ｉなどを添加してマグネシウムの
表面を活性化し反応を促進してもかまわない。ＴＨＦの
かわりにジエチルエーテルを用いる場合には、ジエチル
エーテルの沸点が低いので調製時の発熱に注意をして該
試薬の調製を行うことが好ましい。臭化ビニルを用いる
場合も対応する有機金属試薬を同様に調製することがで
きる。The silicon compound having a silanol group or a hydrolyzable group X that can be used in the present invention can be used without any particular limitation. As the compound having one silicon atom, R n SiX 4-n (R is an organic group having 20 or less carbon atoms, X is a silanol group or a hydrolyzable group, and n is 0
(An integer selected from -3). Specific compounds are exemplified below. SiCl
4 , MeSiCl 3 , MeHSiCl 2 , Me 2 SiC
l 2 , Me 3 SiCl, EtMeSiCl 2 , PhMeS
iCl 2 , Me 2 HSiCl, PhSiCl 3 , Si (O
Me) 4 , MeSi (OMe) 3 , MeHSi (OMe)
2 , Me 2 Si (OMe) 2 , Me 3 SiOMe, EtMe
Si (OMe) 2 , Me 2 HSi (OMe), PhMeS
i (OMe) 2 , PhSi (OMe) 3 , PhMeSi
(OMe) 2 , Si (OEt) 4 , MeSi (OE
t) 3 , MeHSi (OEt) 2 , Me 2 Si (OE
t) 2 , Me 3 SiOMe, EtMeSi (OMe) 2 ,
MeHSi (OEt), MeSi (Oi-Pr) 3 , Me
2 Si (Oi-Pr) 2 , PhMeSi (Oi-Pr) 2,
MeSi (OC = OCH 3 ) 3 , Me 2 Si (OC = OC
H 3 ) 2 , PhMeSi (OC = OCH 3 ) 2 , MeSi
(O (C = CH 2 ) CH 3 ) 3 , Me 2 Si (O (C = CH
2) CH 3) 2, PhMeSi (O (C = CH 2) C
H 3 ) 2 , MeSi (ON = CMe 2 ) 3 , Me 2 Si (O
N = CMe 2 ) 2 , PhMeSi (ON = CMe 2 ) 2 , M
eSi (N (Et) (C = O) CH 3 ) 3 , Me 2 Si
(N (Et) (C = O) CH 3 ) 2 , PhMeSi (N
Specific examples of (Et) (C ＝ O) CH 3 ) 2 and silicon compounds having two or more silicon atoms include the following compounds. ClSi (Me) 2 OSi (Me) 2 Cl ClSi (Me) 2 (p-Ph) Si (Me) 2 Cl ClSi (Me) 2 OSi (Me) 2 OSi (Me) 2 C
l ((Cl) (Me) 2 Si) 3 Ph The vinyl group-containing organometallic reagent which can be usually used in the present invention includes vinyl magnesium chloride THF solution, vinyl magnesium bromide THF solution, vinyl magnesium chloride diethyl ether solution, And vinylmagnesium bromide diethyl ether solution. The vinylmagnesium chloride THF solution can be prepared by introducing vinyl chloride into a mixture of magnesium and THF. BrC
H 2 CH 2 Br or CH 3 I may be added to activate the surface of magnesium to promote the reaction. When diethyl ether is used instead of THF, it is preferable to prepare the reagent while paying attention to the heat generated during the preparation because the boiling point of diethyl ether is low. When using vinyl bromide, the corresponding organometallic reagent can be similarly prepared.

【０００５】[0005]

【発明の実施の形態】本発明ではケイ素化合物（１）と
有機金属試薬（２）とを反応させてビニルシリル基含有
ケイ素化合物（３）を得る方法を提供するのであるが、
（１）と（２）との反応のさせ方については特に制限は
ない。（１）と（２）とを反応させる時には溶媒を用い
てもかまわない。ＴＨＦ，ジエチルエーテル、ジブチル
エーテル、トルエン、キシレン、ベンゼン、ヘキサン、
ヘプタン、クロロホルム、塩化メチレン、などを１種ま
たは２種以上用いることができる。DESCRIPTION OF THE PREFERRED EMBODIMENTS The present invention provides a method for reacting a silicon compound (1) with an organometallic reagent (2) to obtain a vinylsilyl group-containing silicon compound (3).
There is no particular limitation on how to react (1) and (2). When reacting (1) and (2), a solvent may be used. THF, diethyl ether, dibutyl ether, toluene, xylene, benzene, hexane,
One or more of heptane, chloroform, methylene chloride and the like can be used.

【０００６】特別な装置を用いる必要はなく、有機合成
反応で用いられている通常の操作方法で（３）を好適に
実施することができる。たとえば、（１）の溶液中に
（２）溶液を滴下する方法、逆に（２）の溶液に（１）
の溶液を滴下する方法などが例示される。一般上記反応
は発熱反応となるので、コントロールしながらあるいは
冷却しながら滴下する方法を用いてもよい。また場合に
よっては、ビニル基含有有機金属試薬（２）を反応系中
で調製し、調製直後系中に共存するケイ素化合物（１）
と反応させてもよい。[0006] It is not necessary to use a special apparatus, and (3) can be suitably carried out by a usual operation method used in an organic synthesis reaction. For example, a method of dropping the solution (2) into the solution of (1), and conversely, adding the solution (1) to the solution of (2)
A method of dropping a solution of the above is exemplified. In general, since the above reaction is exothermic, a method of dropping while controlling or cooling may be used. In some cases, a vinyl group-containing organometallic reagent (2) is prepared in a reaction system, and a silicon compound (1) which coexists in the system immediately after preparation.
May be allowed to react.

【０００７】本反応に基づいて、例えば下記の化合物を
得ることができる。 Ｍｅ2Ｓｉ（ＣＨ＝ＣＨ2）2、ＰｈＭｅ（ＣＨ＝ＣＨ2）
2、ＭｅＳｉ（ＣＨ＝ＣＨ2）3、ＥｔＭｅＳｉ（ＣＨ＝
ＣＨ2）2、 ＣＨ2＝ＣＨＳｉ（Ｍｅ）2（ｐ-Ｐｈ）Ｓｉ（Ｍｅ）2Ｃ
Ｈ＝ＣＨ2、 ＣＨ2＝ＣＨＳｉ（Ｍｅ）2（ｍ-Ｐｈ）Ｓｉ（Ｍｅ）2Ｃ
Ｈ＝ＣＨ2、 ＣＨ2＝ＣＨＳｉ（Ｍｅ）2ＯＳｉ（Ｍｅ）2ＣＨ＝Ｃ
Ｈ2、 ＣＨ2＝ＣＨＳｉ（Ｍｅ）2ＯＳｉ（Ｍｅ）2Ｓｉ（Ｍ
ｅ2）ＣＨ＝ＣＨ2、 ＣＨ2＝ＣＨＳｉ（Ｍｅ）2ＣＨ2Ｓｉ（Ｍｅ）2ＣＨ＝Ｃ
Ｈ2、 ＣＨ2＝ＣＨＳｉ（Ｍｅ）2ＣＨ2ＣＨ2Ｓｉ（Ｍｅ）2Ｃ
Ｈ＝ＣＨ2、 （ＣＨ2＝ＣＨＳｉ（Ｍｅ）2）3Ｐｈ 以下に実施例を示すが、本発明はこれらに限定されるも
のではない。Based on this reaction, for example, the following compounds can be obtained. Me 2 Si (CH = CH 2 ) 2 , PhMe (CH = CH 2 )
2 , MeSi (CH = CH 2 ) 3 , EtMeSi (CH =
CH 2 ) 2 , CH 2 ＣＨCHSi (Me) 2 (p-Ph) Si (Me) 2 C
H = CH 2 , CH 2 ＣＨCHSi (Me) 2 (m-Ph) Si (Me) 2 C
H = CH 2 , CH 2 ＣＨCHSi (Me) 2 OSi (Me) 2 CH ＝ C
H 2 , CH 2 ＣＨCHSi (Me) 2 OSi (Me) 2 Si (M
e 2) CH = CH 2, CH 2 = CHSi (Me) 2 CH 2 Si (Me) 2 CH = C
H 2 , CH 2 ＣＨCHSi (Me) 2 CH 2 CH 2 Si (Me) 2 C
H = CH 2 , (CH 2 ＣＨCHSi (Me) 2 ) 3 Ph Examples are shown below, but the present invention is not limited to these.

【０００８】[0008]

【実施例】【Example】

（実施例１）ジメチルジクロルシラン１２．９ｇ（０．
１ｍｏｌ）とＴＨＦ２０ｍＬを５００ｍＬ４口フラスコ
に仕込み、窒素雰囲気下ビニルマグネシウムクロライド
ＴＨＦ溶液（１．０Ｍ濃度）２００ｍＬを均圧管付き滴
下ロートから２時間かけて滴下した。穏やかな発熱が観
察された。滴下終了後反応混合物を加熱しＴＨＦを２時
間還流させた。生成した塩をまず濾過後、ろ液からＴＨ
Ｆを蒸留により除去した。残さを再度濾過、ペンタンで
洗浄し、ろ液を蒸留精製することにより、ジメチルジビ
ニルシラン８．３ｇを得た（収率７４％）。 （実施例２）メチルフェニルジクロルシラン１９．１ｇ
（０．１ｍｍｏｌ）とＴＨＦ３０ｍＬを５００ｍＬ４口
フラスコに仕込み、窒素雰囲気下、塩化ビニルより調製
したビニルマグネシウムクロライドＴＨＦ溶液（１．０
Ｍ濃度）２００ｍＬを均圧管付き滴下ロートから２時間
かけて滴下した。穏やかな発熱が観察された。滴下終了
後反応混合物を加熱しＴＨＦを２時間還流させた。生成
した塩を濾過した後ＴＨＦを減圧留去した。残さにヘキ
サン１００ｍＬを加えよくかき混ぜた後析出した塩を再
度濾過した。ろ液からヘキサンを減圧留去後、粗生成物
を蒸留に供し、ジビニルメチルフェニルシラン１５．７
ｇを得た（収率９０％）。 （実施例３）フェニルトリエトキシシラン２４．０ｇ
（０．１ｍｏｌ）とＴＨＦ３０ｍＬを５００ｍＬ４口フ
ラスコに仕込み、窒素雰囲気下ビニルマグネシウムブロ
マイドＴＨＦ溶液（１．０Ｍ濃度）３００ｍＬを均圧管
付き滴下ロートから３時間かけて滴下した。３時間加熱
しＴＨＦを還流させた後、室温で１夜間放置した。ヘキ
サンを加え加水分解分液した後、有機層を飽和食塩水で
洗浄し無水硫酸ナトリウムで乾燥した。溶媒を減圧留去
した後、蒸留により、フェニルトリビニルシラン１５．
３ｇを得た（収率８２％）。 （実施例４）１，４−ビス（ジメチルシリル）ベンゼン
１０ｇ（３８ｍｍｏｌ）とＴＨＦ１０ｍＬを３００ｍＬ
４口フラスコに仕込み、窒素雰囲気下ビニルマグネシウ
ムクロライドＴＨＦ溶液（１．０Ｍ濃度）７６ｍＬを均
圧管付き滴下ロートから３０分かけて滴下した。穏やか
な発熱が観察された。滴下終了後反応混合物を加熱しＴ
ＨＦを２時間還流させた。生成した塩を濾過し、ろ液を
減圧留去してＴＨＦを除去した。残さにヘキサンを加え
析出した塩を再度濾過し、ろ液を蒸留することにより、
１，４−ビス（ジメチルビニルシリル）ベンゼン７．３
ｇを得た（収率７８％）。(Example 1) 12.9 g of dimethyldichlorosilane (0.
1 mol) and 20 mL of THF were placed in a 500 mL four-necked flask, and 200 mL of a vinylmagnesium chloride THF solution (1.0 M concentration) was dropped from a dropping funnel equipped with a pressure equalizing tube over 2 hours under a nitrogen atmosphere. A mild exotherm was observed. After completion of the dropwise addition, the reaction mixture was heated to reflux THF for 2 hours. The resulting salt is filtered first, and the filtrate is treated with TH.
F was removed by distillation. The residue was filtered again, washed with pentane, and the filtrate was purified by distillation to obtain 8.3 g of dimethyldivinylsilane (yield 74%). (Example 2) 19.1 g of methylphenyldichlorosilane
(0.1 mmol) and 30 mL of THF were charged into a 500 mL four-necked flask, and a vinylmagnesium chloride THF solution (1.0 mL) prepared from vinyl chloride under a nitrogen atmosphere.
(M concentration) 200 mL was dropped from the dropping funnel with a pressure equalizing tube over 2 hours. A mild exotherm was observed. After completion of the dropwise addition, the reaction mixture was heated to reflux THF for 2 hours. After filtration of the formed salt, THF was distilled off under reduced pressure. After adding 100 mL of hexane to the residue and stirring well, the precipitated salt was filtered again. After evaporating hexane from the filtrate under reduced pressure, the crude product was subjected to distillation to obtain divinylmethylphenylsilane (15.7).
g was obtained (yield 90%). (Example 3) 24.0 g of phenyltriethoxysilane
(0.1 mol) and 30 mL of THF were charged into a 500 mL four-necked flask, and 300 mL of a vinylmagnesium bromide THF solution (1.0 M concentration) was dropped from a dropping funnel equipped with a pressure equalizing tube over 3 hours under a nitrogen atmosphere. After heating for 3 hours to reflux THF, the mixture was allowed to stand at room temperature overnight. After hexane was added for hydrolysis and separation, the organic layer was washed with saturated saline and dried over anhydrous sodium sulfate. After the solvent was distilled off under reduced pressure, phenyltrivinylsilane was obtained by distillation.
3 g was obtained (82% yield). Example 4 300 g of 10 g (38 mmol) of 1,4-bis (dimethylsilyl) benzene and 10 mL of THF
The mixture was charged in a four-necked flask, and 76 mL of a vinylmagnesium chloride THF solution (1.0 M concentration) was added dropwise from a dropping funnel equipped with a pressure equalizing tube over 30 minutes under a nitrogen atmosphere. A mild exotherm was observed. After the dropwise addition, the reaction mixture is heated to T
HF was refluxed for 2 hours. The generated salt was filtered, and the filtrate was distilled off under reduced pressure to remove THF. Hexane was added to the residue, the precipitated salt was filtered again, and the filtrate was distilled,
1,4-bis (dimethylvinylsilyl) benzene 7.3
g was obtained (78% yield).

【０００９】[0009]

【発明の効果】本発明により、有用なビニルシリル基含
有ケイ素化合物を容易に好収率で得ることができる。According to the present invention, useful silicon compounds containing a vinylsilyl group can be easily obtained in good yield.

Claims (1)

【特許請求の範囲】[Claims] 【請求項１】シラノール基または加水分解性基Ｘを有す
るケイ素化合物（１）とビニル基含有有機金属試薬
（２）とを反応させて、（１）中の基Ｘをビニル基に置
換し、ビニル基含有ケイ素化合物（３）を製造する方
法。1. A silicon compound (1) having a silanol group or a hydrolyzable group X is reacted with a vinyl group-containing organometallic reagent (2) to replace the group X in (1) with a vinyl group. A method for producing a vinyl group-containing silicon compound (3).
JP29363996A 1996-11-06 1996-11-06 Production of vinylsilyl group-containing silicone compound Pending JPH10139784A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP29363996A JPH10139784A (en) 1996-11-06 1996-11-06 Production of vinylsilyl group-containing silicone compound

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP29363996A JPH10139784A (en) 1996-11-06 1996-11-06 Production of vinylsilyl group-containing silicone compound

Publications (1)

Publication Number Publication Date
JPH10139784A true JPH10139784A (en) 1998-05-26

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