JPH085900B2 - Vinyl group-containing siloxane compound and method for producing the same - Google Patents
Vinyl group-containing siloxane compound and method for producing the sameInfo
- Publication number
- JPH085900B2 JPH085900B2 JP25479391A JP25479391A JPH085900B2 JP H085900 B2 JPH085900 B2 JP H085900B2 JP 25479391 A JP25479391 A JP 25479391A JP 25479391 A JP25479391 A JP 25479391A JP H085900 B2 JPH085900 B2 JP H085900B2
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- group
- siloxane compound
- vinyl group
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Description
【０００１】[0001]
【産業上の利用分野】本発明は、付加反応型シリコーン
樹脂、ＵＶ硬化型シリコーン樹脂等のベースシロキサン
オイルのストッパーやその合成中間体などとして有用な
ビニル基含有シロキサン化合物及びその製造方法に関す
る。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a vinyl group-containing siloxane compound useful as a stopper for base siloxane oil such as addition reaction type silicone resin and UV-curable silicone resin, a synthetic intermediate thereof, and a method for producing the same.
【０００２】[0002]
【従来の技術及び発明が解決しようとする課題】従来、
付加反応型シリコーン樹脂、ＵＶ硬化型シリコーン樹脂
等のベースシロキサンとして、末端をトリビニルシリル
基やジビニルシリル基で封鎖されたポリシロキサンが使
用されている。これらポリシロキサンの合成に用いる中
間シロキサンとしては、下記構造のヘキサビニルジシロ
キサン、テトラビニルジシロキサン等が知られている。2. Description of the Related Art Conventionally, the problems to be solved by the invention
As a base siloxane such as an addition reaction type silicone resin or a UV curing type silicone resin, a polysiloxane having a terminal blocked with a trivinylsilyl group or a divinylsilyl group is used. Hexavinyldisiloxane and tetravinyldisiloxane having the following structures are known as intermediate siloxanes used in the synthesis of these polysiloxanes.
【０００３】[0003]
【化３】 [Chemical 3]
【０００４】しかし、これらシロキサン化合物は純シリ
コーン系ＵＶ硬化樹脂として優れた硬化特性が得られ、
既に実用化されているが、有機系ＵＶ硬化樹脂（例えば
アクリル系樹脂）等に比べるとやや硬化速度に劣る面が
あり、このため、より優れた硬化性を有するビニル基含
有シロキサン化合物の開発が望まれる。However, these siloxane compounds have excellent curing characteristics as a pure silicone UV curing resin,
Although it has already been put to practical use, it has a slightly slower curing speed than organic UV curable resins (eg acrylic resins) and so on. Therefore, the development of vinyl group-containing siloxane compounds having superior curability has been developed. desired.
【０００５】本発明は上記事情に鑑みなされたもので、
速硬化性等の特性に優れたビニル基含有シロキサン化合
物及びその製造方法を提供することを目的とする。The present invention has been made in view of the above circumstances.
It is an object of the present invention to provide a vinyl group-containing siloxane compound having excellent properties such as fast curing property and a method for producing the same.
【０００６】[0006]
【課題を解決するための手段及び作用】本発明者は上記
目的を達成するため鋭意検討を重ねた結果、下記一般式
（２）で示されるシロキサン化合物と下記一般式（３）
で示されるハロゲン化アルキル化合物とをグリニャール
反応させた後、蒸留することにより得られる下記一般式
（１）で示される新規なビニル基含有シロキサン化合物
が、非常に優れた硬化性を有し、付加反応型シリコーン
樹脂、ＵＶ硬化型シリコーン樹脂等のベースシロキサン
オイルのストッパーやその合成中間体などとして有効で
あることを知見し、本発明をなすに至ったものである。Means and Actions for Solving the Problems As a result of extensive studies conducted by the present inventor to achieve the above object, the siloxane compound represented by the following general formula (2) and the following general formula (3)
A novel vinyl group-containing siloxane compound represented by the following general formula (1) obtained by subjecting a halogenated alkyl compound represented by The present invention has been completed by finding that it is effective as a stopper of base siloxane oil such as reactive silicone resin and UV curable silicone resin and its synthetic intermediate.
【０００７】[0007]
【化４】 （但し、上記式中Ｒはビニル基、Ｒ1は脂肪族不飽和結
合を除く同一又は異種の置換又は非置換の炭素数１〜１
０の１価炭化水素基であり、ｎは０〜１００の整数であ
る。）[Chemical 4] (However, in the above formula, R is a vinyl group, R 1 is the same or different substituted or unsubstituted C 1 to 1 except for an aliphatic unsaturated bond.
It is a monovalent hydrocarbon group of 0, and n is an integer of 0 to 100. )
【０００８】[0008]
【化５】 （但し、上記式中Ｒ1及びｎは上記と同様であり、Ｒ2は
ビニル基、Ｘ1はハロゲン原子又はアルコキシ基、Ｘ2は
ハロゲン原子である。）[Chemical 5] (However, in the above formula, R 1 and n are the same as above, R 2 is a vinyl group, X 1 is a halogen atom or an alkoxy group, and X 2 is a halogen atom.)
【０００９】以下、本発明につき更に詳細に説明する
と、本発明のビニル基含有シロキサン化合物は、下記一
般式（１）で示されるものである。The present invention will be described in more detail below. The vinyl group-containing siloxane compound of the present invention is represented by the following general formula (1).
【００１０】[0010]
【化６】 [Chemical 6]
【００１１】ここで、上記（１）式中Ｒはビニル基であ
り、また、Ｒ1は同一でも異なっていてもよいが、脂肪
族不飽和結合を除く、置換又は非置換の炭素数１〜１０
の１価炭化水素基であり、好ましくは炭素数１〜８の一
価炭化水素基である。このＲ1としては、例えばメチル
基，エチル基，プロピル基，ブチル基等やこれらの基の
炭素原子に結合している水素原子の一部又は全部をハロ
ゲン原子で置換した基などの炭素数１〜６の低級アルキ
ル基、フェニル基，トリル基，ナフチル基やこれらの基
の炭素原子に結合した水素原子の一部又は全部をハロゲ
ン原子で置換した基等の炭素数６〜１０のアリール基、
ベンジル基，フェニルエチル基やこれらの基の炭素原子
に結合した水素原子の一部又は全部をハロゲン原子で置
換した基等の炭素数７〜１０のアラルキル基などが挙げ
られる。また、ｎは０〜１００の整数、好ましくは０〜
１０の整数である。In the above formula (1), R is a vinyl group, and R 1 may be the same or different, but the substituted or unsubstituted C 1 to C 1 excluding the aliphatic unsaturated bond. 10
Is a monovalent hydrocarbon group, preferably a monovalent hydrocarbon group having 1 to 8 carbon atoms. The R 1 is, for example, a methyl group, an ethyl group, a propyl group, a butyl group, or the like, or a group in which some or all of the hydrogen atoms bonded to the carbon atoms of these groups are replaced by halogen atoms An aryl group having 6 to 10 carbon atoms, such as a lower alkyl group having 6 to 6, a phenyl group, a tolyl group, a naphthyl group, or a group in which some or all of the hydrogen atoms bonded to the carbon atoms of these groups are substituted with halogen atoms,
Examples thereof include a benzyl group, a phenylethyl group, and an aralkyl group having 7 to 10 carbon atoms such as a group in which a part or all of hydrogen atoms bonded to carbon atoms of these groups are substituted with halogen atoms. Further, n is an integer of 0 to 100, preferably 0.
It is an integer of 10.
【００１２】このような（１）式のビニル基含有シロキ
サン化合物として具体的には、下記構造のものが例示さ
れる。Specific examples of such a vinyl group-containing siloxane compound of the formula (1) include those having the following structures.
【００１３】[0013]
【化７】 （但し、ｎは前記と同様の意味を表わす。）[Chemical 7] (However, n has the same meaning as described above.)
【００１４】上記（１）式のビニル基含有シロキサン化
合物は、例えば下記一般式（２）で示されるシロキサン
化合物と下記一般式（３）で示されるハロゲン化アルキ
ル化合物とをグリニャール反応させた後、蒸留すること
により、工業的に有利に合成することができる。The vinyl group-containing siloxane compound of the above formula (1) is obtained by, for example, reacting a siloxane compound represented by the following general formula (2) with a halogenated alkyl compound represented by the following general formula (3) by a Grignard reaction. By distilling, it can be synthesized industrially advantageously.
【００１５】[0015]
【化８】 （但し、上記式中Ｒ1及びｎは上記と同様であり、Ｒ2は
ビニル基、Ｘ1は例えば臭素、塩素、ヨウ素等のハロゲ
ン原子又は例えばメトキシ基、エトキシ基、プロポキシ
基、ブトキシ基、メトキシエトキシ基、エトキシエトキ
シ基等のアルコキシ基、Ｘ2は例えば臭素、塩素、ヨウ
素等のハロゲン原子である。）Embedded image (However, in the above formula, R 1 and n are the same as above, R 2 is a vinyl group, X 1 is a halogen atom such as bromine, chlorine, iodine, or a methoxy group, an ethoxy group, a propoxy group, a butoxy group, An alkoxy group such as a methoxyethoxy group and an ethoxyethoxy group, and X 2 is a halogen atom such as bromine, chlorine and iodine.)
【００１６】なお、上記（２）式のシロキサン化合物
は、例えば下記一般式（４）で示される化合物と下記一
般式（５）で示される化合物、又は下記一般式（６）で
示される化合物と下記一般式（７）で示される化合物と
を白金触媒を用いて通常の方法で付加反応させることに
より合成することができる。The siloxane compound represented by the above formula (2) is, for example, a compound represented by the following general formula (4) and a compound represented by the following general formula (5), or a compound represented by the following general formula (6). It can be synthesized by subjecting the compound represented by the following general formula (7) to an addition reaction by a usual method using a platinum catalyst.
【００１７】[0017]
【化９】 （但し、上記式中Ｒ1、Ｘ1、ｎは上記と同様である。）[Chemical 9] (However, in the above formula, R 1 , X 1 , and n are the same as above.)
【００１８】更に、上述したグリニャール反応は、テト
ラヒドロフラン等の溶媒中に上記（３）式のハロゲン化
アルキル化合物と例えば金属マグネシウム等を加えてグ
リニャール試薬を調製した後、これを室温以下に冷却
し、次いでこのグリニャール試薬に不活性ガス雰囲気下
にて上記（２）式のシロキサン化合物を滴下して反応さ
せるか、或いは逆に（２）式のシロキサン化合物を溶媒
中に添加して希釈し、冷却、攪拌した後、これに上述の
ようにして予め調製したグリニャール試薬を滴下しても
よい。Further, in the Grignard reaction described above, a Grignard reagent is prepared by adding the halogenated alkyl compound of the above formula (3) and metal magnesium, for example, to a solvent such as tetrahydrofuran, and then cooling this to room temperature or below. Then, the siloxane compound of the formula (2) is added dropwise to the Grignard reagent in an inert gas atmosphere for reaction, or conversely, the siloxane compound of the formula (2) is added to a solvent to dilute and cool, After stirring, the Grignard reagent prepared in advance as described above may be added dropwise thereto.
【００１９】このグリニャール反応において、グリニャ
ール試薬は（３）式のハロゲン化アルキル化合物と上記
金属とをモル比で０．５：１〜２：１、特に１：１〜
１．２：１の割合で混合して調製することが好ましい。
更に、（２）式のシロキサン化合物とグリニャール試薬
との混合割合は、モル比で１：６〜１：１５、特に１：
６〜１：８とすることが好ましく、また、上記（２）式
のシロキサン化合物と（３）式のハロゲン化アルキル化
合物との混合割合がモル比で１：３〜１：３０、特に
１：６〜１：９．６となるようにすることが望ましい。
（２）式のシロキサン化合物とグリニャール試薬又は
（３）式のハロゲン化アルキル化合物との混合割合が上
記範囲外では目的とする（１）式で示される化合物が得
られないか、あるいは得られても反応収率が非常に低く
なる場合がある。In this Grignard reaction, the Grignard reagent is a halogenated alkyl compound of the formula (3) and the above metal in a molar ratio of 0.5: 1 to 2: 1, particularly 1: 1 to 1.
It is preferable to mix and prepare in the ratio of 1.2: 1.
Furthermore, the mixing ratio of the siloxane compound of the formula (2) and the Grignard reagent is 1: 6 to 1:15, and particularly 1: 1:
The mixing ratio of the siloxane compound of the formula (2) to the alkyl halide compound of the formula (3) is preferably 1: 3 to 1:30, and particularly 1: 1. It is desirable that the ratio is 6 to 1: 9.6.
If the mixing ratio of the siloxane compound of the formula (2) and the Grignard reagent or the alkyl halide compound of the formula (3) is out of the above range, the desired compound represented by the formula (1) cannot be obtained or is obtained. However, the reaction yield may be very low.
【００２０】グリニャール反応の反応条件は、−５０℃
〜溶媒の沸点、特に０℃〜室温で５分間〜６時間、特に
３０分間〜３時間とすることが好ましく、反応温度が−
５０℃より低いと反応が遅くなる場合があり、溶媒の沸
点より高くなると副反応が発生して収率が悪くなる場合
がある。また、反応時間が５分間に満たないと反応が完
了しない場合があり、６時間を超えると反応がそれ以上
進行せず時間的に無駄となる場合がある。The reaction conditions for the Grignard reaction are -50 ° C.
~ Boiling point of solvent, particularly 0 ° C to room temperature, 5 minutes to 6 hours, preferably 30 minutes to 3 hours, and reaction temperature-
If it is lower than 50 ° C., the reaction may be slow, and if it is higher than the boiling point of the solvent, a side reaction may occur and the yield may be deteriorated. Further, if the reaction time is less than 5 minutes, the reaction may not be completed, and if it exceeds 6 hours, the reaction may not proceed any more and may be wasted in time.
【００２１】更に、反応に使用される溶媒としては、上
記したテトラヒドロフランの他に反応を妨害しないもの
であれば種々のものを用いることができる。なお、反応
液の希釈割合は反応熱、容積効率等を考慮して適宜決め
ることができ、溶媒の使用量はこれらに応じて調整する
ことができる。Further, as the solvent used in the reaction, various solvents other than the above-mentioned tetrahydrofuran can be used as long as they do not interfere with the reaction. The dilution ratio of the reaction solution can be appropriately determined in consideration of reaction heat, volumetric efficiency, etc., and the amount of the solvent used can be adjusted according to these.
【００２２】また、シロキサン化合物とグリニャール試
薬との反応は、通常不活性ガス雰囲気で進めることが望
ましく、不活性ガスとしては例えばアルゴン、ヘリウ
ム、窒素等の１種を単独で又は２種以上を混合して使用
することができるが、経済性の点からこれらの中でも窒
素ガスが好適に使用される。The reaction between the siloxane compound and the Grignard reagent is usually preferably carried out in an inert gas atmosphere. As the inert gas, for example, argon, helium, nitrogen, etc. may be used alone or in combination of two or more. Among them, nitrogen gas is preferably used from the viewpoint of economy.
【００２３】更に、上記グリニャール反応が終了した後
は上記（１）式のビニル基含有シロキサン化合物を含む
混合物が得られ、この混合物を通常の方法で蒸留するこ
とにより、目的とする上記（１）式のビニル基含有シロ
キサン化合物を得ることができる。Further, after the Grignard reaction is completed, a mixture containing the vinyl group-containing siloxane compound of the above formula (1) is obtained, and this mixture is distilled by a conventional method to obtain the desired (1) above. A vinyl group-containing siloxane compound of the formula can be obtained.
【００２４】[0024]
【発明の効果】本発明の上記（１）式のビニル基含有シ
ロキサン化合物は、速硬化性に優れており、付加反応型
シリコーン樹脂、ＵＶ硬化型シリコーン樹脂等のベース
シロキサンオイルのストッパーやその合成中間体などと
して有用である。また、本発明方法によれば（１）式の
ビニル基含有シロキサン化合物を工業的に有利に合成す
ることができる。EFFECT OF THE INVENTION The vinyl group-containing siloxane compound of the above formula (1) of the present invention is excellent in quick-curing property, and is a stopper for base siloxane oil such as addition reaction type silicone resin and UV curing type silicone resin and its synthesis. It is useful as an intermediate. Further, according to the method of the present invention, the vinyl group-containing siloxane compound of the formula (1) can be synthesized industrially advantageously.
【００２５】[0025]
【実施例】以下、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 now be specifically described with reference to examples, but the present invention is not limited to the following examples. All parts in each example are parts by weight.
【００２６】〔実施例〕ジハイドロテトラメチルジシロ
キサン１３４部とトリメトキシシラン３２５．６部を反
応器に仕込んで加熱し、アルコール変性塩化白金酸溶液
０．０５部を滴下して１１０℃で反応を２時間行ない、
生成したシロキサン化合物が含まれている混合物を得
た。この混合物を蒸留したところ、下記（８）式で示さ
れるシロキサン化合物を単離した。この（８）式のシロ
キサン化合物の核磁気共鳴スペクトルの分析結果を図１
に示す。[Example] 134 parts of dihydrotetramethyldisiloxane and 325.6 parts of trimethoxysilane were charged into a reactor and heated, and 0.05 part of alcohol-modified chloroplatinic acid solution was added dropwise to react at 110 ° C. For 2 hours,
A mixture containing the produced siloxane compound was obtained. When this mixture was distilled, a siloxane compound represented by the following formula (8) was isolated. The analysis result of the nuclear magnetic resonance spectrum of the siloxane compound of the formula (8) is shown in FIG.
Shown in
【００２７】[0027]
【化１０】 Ｂｐ：１２０〜１２１℃／２．５ｍｍＨｇ 収率：
５６％[Chemical 10] Bp: 120 to 121 ° C./2.5 mmHg Yield:
56%
【００２８】次に、金属マグネシウム１６０部、ビニル
ブロマイド７７０部をテトラヒドロフラン溶媒を用いて
グリニャール試薬を生成させ、これに上記（８）式のシ
ロキサン化合物４３０部を２０〜３０℃で１時間かけて
滴下し、更に水洗分離後に蒸留を行ったところ、下記
（９）式で示されるビニル基含有シロキサン化合物が得
られた。この（９）式のビニル基含有シロキサン化合物
の核磁気共鳴スペクトル、マススペクトル、赤外線吸収
スペクトルの分析結果をそれぞれ図２〜４に示す。ま
た、元素分析の結果は下記のとおりであった。Next, 160 parts of metallic magnesium and 770 parts of vinyl bromide were used to form a Grignard reagent using a tetrahydrofuran solvent, and 430 parts of the siloxane compound represented by the above formula (8) was added dropwise thereto at 20 to 30 ° C. for 1 hour. Then, after washing with water and separation, distillation was carried out to obtain a vinyl group-containing siloxane compound represented by the following formula (9). 2 to 4 show the results of analysis of the nuclear magnetic resonance spectrum, mass spectrum and infrared absorption spectrum of the vinyl group-containing siloxane compound of the formula (9). The results of elemental analysis are as follows.
【００２９】[0029]
【化１１】 Ｂｐ：１５４℃／３ｍｍＨｇ 収率：７１％ 元素分析結果（％）：Ｃ20Ｈ38Ｏ1Ｓｉ4 Ｃ Ｈ Ｓｉ 測定値 ２４０．３１ ３８．３８ １１２．０３ 理論値 ２４０．２２ ３８．３０ １１２．３４[Chemical 11] Bp: 154 ° C./3 mmHg Yield: 71% Elemental analysis result (%): C 20 H 38 O 1 Si 4 C H Si Measured value 240.31 38.38 112.03 Theoretical value 240.22 38.30 112. 34
【図１】 （８）式のシロキサン化合物の核磁気共鳴ス
ペクトルである。FIG. 1 is a nuclear magnetic resonance spectrum of a siloxane compound represented by formula (8).
【図２】 （９）式のビニル基含有シロキサン化合物の
核磁気共鳴スペクトルである。FIG. 2 is a nuclear magnetic resonance spectrum of a vinyl group-containing siloxane compound represented by formula (9).
【図３】 （９）式のビニル基含有シロキサン化合物の
マススペクトルである。FIG. 3 is a mass spectrum of the vinyl group-containing siloxane compound represented by the formula (9).
【図４】 （９）式のビニル基含有シロキサン化合物の
マススペクトルである。FIG. 4 is a mass spectrum of the vinyl group-containing siloxane compound represented by the formula (9).
【図５】 （９）式のビニル基含有シロキサン化合物の
赤外線吸収スペクトルである。FIG. 5 is an infrared absorption spectrum of a vinyl group-containing siloxane compound represented by formula (9).
Claims (2)
有シロキサン化合物。 【化１】 （但し、上記式中Ｒはビニル基、Ｒ1は脂肪族不飽和結
合を除く同一又は異種の置換又は非置換の炭素数１〜１
０の１価炭化水素基であり、ｎは０〜１００の整数であ
る。）1. A vinyl group-containing siloxane compound represented by the following general formula (1). Embedded image (However, in the above formula, R is a vinyl group, R 1 is the same or different substituted or unsubstituted C 1 to 1 except for an aliphatic unsaturated bond.
It is a monovalent hydrocarbon group of 0, and n is an integer of 0 to 100. )
記一般式（３）で示される化合物とをグリニャール反応
させた後、蒸留する請求項１記載のビニル基含有シロキ
サン化合物の製造方法。 【化２】 （但し、上記式中Ｒ1は脂肪族不飽和結合を除く同一又
は異種の置換又は非置換の炭素数１〜１０の１価炭化水
素基であり、Ｒ2はビニル基、Ｘ1はハロゲン原子又はア
ルコキシ基、Ｘ2はハロゲン原子であり、ｎは０〜１０
０の整数である。）2. The method for producing a vinyl group-containing siloxane compound according to claim 1, wherein the compound represented by the following general formula (2) and the compound represented by the following general formula (3) are subjected to a Grignard reaction and then distilled. Embedded image (However, in the above formula, R 1 is the same or different substituted or unsubstituted monovalent hydrocarbon group having 1 to 10 carbon atoms excluding the aliphatic unsaturated bond, R 2 is a vinyl group, and X 1 is a halogen atom. Alternatively, an alkoxy group, X 2 is a halogen atom, and n is 0 to 10
It is an integer of 0. )
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP25479391A JPH085900B2 (en) | 1991-09-05 | 1991-09-05 | Vinyl group-containing siloxane compound and method for producing the same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP25479391A JPH085900B2 (en) | 1991-09-05 | 1991-09-05 | Vinyl group-containing siloxane compound and method for producing the same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH0559070A JPH0559070A (en) | 1993-03-09 |
| JPH085900B2 true JPH085900B2 (en) | 1996-01-24 |
Family
ID=17269971
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP25479391A Expired - Fee Related JPH085900B2 (en) | 1991-09-05 | 1991-09-05 | Vinyl group-containing siloxane compound and method for producing the same |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH085900B2 (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6919481B1 (en) | 1998-07-22 | 2005-07-19 | Nof Corporation | Alkoxyamines containing a vinyl group, their applications and methods of their production |
| JP4414269B2 (en) * | 2004-04-23 | 2010-02-10 | シーケーディ株式会社 | Flow rate characteristic adjustment mechanism of electromagnetic proportional valve and flow rate characteristic adjustment method using the same |
| JP6536414B2 (en) * | 2016-01-06 | 2019-07-03 | 信越化学工業株式会社 | Addition curable thermoplastic silicone composition, thermoplastic silicone cured product and method for producing the same |
| KR101972761B1 (en) * | 2017-10-31 | 2019-04-29 | 한국과학기술연구원 | Silylcarbosiloxane derivatives for cross-linker and the fabrication method of the same |
-
1991
- 1991-09-05 JP JP25479391A patent/JPH085900B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0559070A (en) | 1993-03-09 |
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