JPH0730092B2 - Vinyloxypropyl trimethylsiloxysilane compound - Google Patents
Vinyloxypropyl trimethylsiloxysilane compoundInfo
- Publication number
- JPH0730092B2 JPH0730092B2 JP60220187A JP22018785A JPH0730092B2 JP H0730092 B2 JPH0730092 B2 JP H0730092B2 JP 60220187 A JP60220187 A JP 60220187A JP 22018785 A JP22018785 A JP 22018785A JP H0730092 B2 JPH0730092 B2 JP H0730092B2
- Authority
- JP
- Japan
- Prior art keywords
- compound
- vinyl ether
- trimethylsiloxysilane
- vinyloxypropyl
- osi
- 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.)
- Expired - Fee Related
Links
Landscapes
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Silicon Polymers (AREA)
Description
【発明の詳細な説明】 本発明は新規化合物、ビニロキシプロピルトリメチルシ
ロキシシラン化合物に係るものである。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a novel compound, a vinyloxypropyltrimethylsiloxysilane compound.
本発明の化合物はシロキサン結合を有する各種重合体を
得る為の共単量体として、特に含弗素重合体中にシリコ
ーンを均一に含有せしめ得る共単量体として有用であ
る。INDUSTRIAL APPLICABILITY The compound of the present invention is useful as a comonomer for obtaining various polymers having a siloxane bond, particularly as a comonomer capable of uniformly containing silicone in a fluorine-containing polymer.
本発明による新規化合物を製造する手段としては、式CH
2＝CHOCH2CH＝CH2で示されるアリルビニルエーテルへの
式HSi(CH3)n[OSi(CH3)3]3-n（ｎ＝0,1,2）で示されるト
リメチルシロキシシランの付加反応を採用することがで
きる。The means for preparing the novel compounds according to the present invention include the formula CH
2 = CHOCH 2 CH = CH formula HSi (CH 3) 2 to allyl vinyl ether represented by n [OSi (CH 3) 3 ] added trimethylsiloxy silane represented by 3-n (n = 0,1,2) A reaction can be employed.
これらを実際反応せしめて本発明による新規化合物を製
造する具体的手段としては、例えば塩化白金酸等の白金
化合物の存在下にイソプロピルアルコール等のアルコー
ルやトルエン等の炭化水素化合物等の溶媒の存在若しく
は不存在下にCH2＝CHOCH2CH＝CH2とHSi(CH3)n[OSi(CH3)
3]3-n（ｎ＝0,1,2）を常温若しくは加熱して一定時間反
応せしめ、その後蒸留により生成物を単離する手段が有
効である。As a specific means for actually reacting these with each other to produce the novel compound, the presence of a solvent such as an alcohol such as isopropyl alcohol or a hydrocarbon compound such as toluene in the presence of a platinum compound such as chloroplatinic acid, or In the absence of CH 2 = CHOCH 2 CH = CH 2 and HSi (CH 3 ) n [OSi (CH 3 )
It is effective to use 3 ] 3-n (n = 0, 1, 2) at room temperature or under heating to react for a certain period of time, and then isolate the product by distillation.
本発明により得られた化合物は、例えばプラスチックレ
ンズの原料として、或はシーラント、コーティング剤、
接着剤の原料として有用である。The compound obtained by the present invention can be used as a raw material for plastic lenses, sealants, coating agents,
It is useful as a raw material for adhesives.
これら用途に用いる為には、更に別の単量体との共重合
体が採用される。かかる共単量体としては、例えばテト
ラフルオロエチレン，クロロトリフルオロエチレン等の
フロロオレフィンや酢酸ビニル，塩化ビニル，アクリロ
ニトリル，アクリル酸誘導体、スチレン，α−オレフィ
ンが挙げられる。For use in these applications, a copolymer with another monomer is adopted. Examples of such comonomers include fluoroolefins such as tetrafluoroethylene and chlorotrifluoroethylene, vinyl acetate, vinyl chloride, acrylonitrile, acrylic acid derivatives, styrene and α-olefins.
次に本発明を実施例により説明する。Next, the present invention will be described with reference to examples.
実施例１ CH2＝CHOC3H6Si(CH3)2[OSi(CH3)3］の合成。Example 1 Synthesis of CH 2 = CHOC 3 H 6 Si (CH 3 ) 2 [OSi (CH 3 ) 3 ].
滴下ロート、攪拌機、冷却器、温度計が用意された四ツ
口フラスコにアリルビニルエーテル1008g（12モル）、
イソプロピルアルコール1008g及びH2PtCl60.492gを仕込
み、加熱を開始して68℃でアリルビニルエーテルの還流
が始まったら滴下ロートよりトリメチルシロキシジメチ
オルシラン1.776g（12モル）の滴下を開始した。２時間
で全量の滴下を終了し、内温は83℃となった。滴下終了
後１時間還流を継続し、アリルビニルエーテルの消失を
確認した。この合成液からイソプロピルアルコールを留
去後,10mmHg,76℃で減圧蒸留を行ない、純度98.5％の頭
記合成物質を1564g、収率73％で得た。Allyl vinyl ether 1008 g (12 mol) in a four-necked flask equipped with a dropping funnel, a stirrer, a condenser, and a thermometer,
1008 g of isopropyl alcohol and 0.492 g of H 2 PtCl 6 were charged, heating was started, and when reflux of allyl vinyl ether started at 68 ° C., 1.776 g (12 mol) of trimethylsiloxydimethyolsilane was added dropwise from the dropping funnel. The dropping of the entire amount was completed in 2 hours, and the internal temperature became 83 ° C. Refluxing was continued for 1 hour after completion of dropping, and disappearance of allyl vinyl ether was confirmed. After isopropyl alcohol was distilled off from this synthetic solution, vacuum distillation was carried out at 10 mmHg and 76 ° C. to obtain 1564 g of the above-mentioned synthetic substance having a purity of 98.5% in a yield of 73%.
構造の同定は元素分析、質量分析、核磁気共鳴スペクタ
ル（プロトン）により行なった。結果を以下に示す。The structure was identified by elemental analysis, mass spectrometry and nuclear magnetic resonance spectroscopy (proton). The results are shown below.
・元素分析 Si:24.2wt％,C:52.4wt％,H:10.3wt％,0:13.1wt％ ・質量分析（EI法） 条件；イオン化電圧70eV,イオン化温度270℃，トラップ
電流60μA,加速電圧3KVMS（m/e）217［Ｍ−CH3］,147
［Ｍ−C3H6OC2H3］,73［Si（CH3）3］ ・核磁気共鳴スペクトル1 HNMR ケミカルシフト（ppm）TMS基準 強度比 （ａ） 0.5 ２ （ｂ） 1.5 ２ （ｃ） 3.5 ２ （ｄ） 3.8 １ （ｅ） 4.1 １ （ｆ） 6.3 １ 実施例２ CH2＝CHOC3H6Si(CH3)[OSi(CH3)3]2の合成。 ・ Elemental analysis Si: 24.2wt%, C: 52.4wt%, H: 10.3wt%, 0: 13.1wt% ・ Mass spectrometry (EI method) conditions: Ionization voltage 70eV, Ionization temperature 270 ℃, Trap current 60μA, Acceleration voltage 3KVMS (m / e) 217 [ M-CH 3], 147
[M-C 3 H 6 OC 2 H 3], 73 [Si (CH 3) 3] · Nuclear magnetic resonance spectrum 1 HNMR chemical shift (ppm) TMS standard intensity ratio (a) 0.5 2 (b) 1.5 2 (c ) 3.5 2 (d) 3.8 1 (e) 4.1 1 (f) 6.3 1 example 2 CH 2 = CHOC 3 H 6 Si (CH 3) [OSi (CH 3) 3] 2 in the synthesis.
実施例１で用いた装置にアリルビニルエーテル840g（10
モル）、イソプロピルアルコール840g及びH2PtCl60.41g
を仕込み、加熱を開始して68℃でアリルビニルエーテル
の還流が始まったら滴下ロートよりビストリメチルシロ
キシメチルシラン2225g（10モル）の滴下を開始した。
３時間で全量の滴下を終了し、内温は83℃となった。滴
下終了後１時間還流を継続し、アリルビニルエーテルの
消失を確認した。この合成液からイソプロピルアルコー
ルを留去後,5mmHg,76℃で減圧蒸留を行ない、純度98％
の頭記合成物質を1990g,収率65％で得た。840 g of allyl vinyl ether (10
Mol), isopropyl alcohol 840g and H 2 PtCl 6 0.41g
Was charged, and when the reflux of allyl vinyl ether started at 68 ° C., 2225 g (10 mol) of bistrimethylsiloxymethylsilane was added dropwise from the dropping funnel.
The dropping of the entire amount was completed in 3 hours, and the internal temperature became 83 ° C. Refluxing was continued for 1 hour after completion of dropping, and disappearance of allyl vinyl ether was confirmed. After isopropyl alcohol was distilled off from this synthetic solution, vacuum distillation was performed at 5 mmHg and 76 ° C to obtain a purity of 98%.
The above synthetic compound was obtained in a yield of 1990 g with a yield of 65%.
構造の同定は元素分析、質量分析、核磁気共鳴スペクタ
ル（プロトン）により行なった。結果を以下に示す。The structure was identified by elemental analysis, mass spectrometry and nuclear magnetic resonance spectroscopy (proton). The results are shown below.
・元素分析 Si:27.4wt％,C:46.9wt％,H:9.8wt％,0:15.9wt％ ・質量分析（EI法） 条件；実施例−１の場合と同様 MS（m/e）291［Ｍ−CH3］,221［Ｍ−C3H6OC2H3］,207
［HSi（OSi（CH3）3)2］,73［（Si（CH3)3］ ・核磁気共鳴スペクトル1 HNMR ケミカルシフト（ppm）TMS基準 強度比 （ａ） 0.5 ２ （ｂ） 1.5 ２ （ｃ） 3.5 ２ （ｄ） 3.8 １ （ｅ） 4.1 １ （ｆ） 6.3 １ 実施例３ CH2＝CHOC3H6Si[OSi(CH3)3]3の合成。 -Elemental analysis Si: 27.4 wt%, C: 46.9 wt%, H: 9.8 wt%, 0: 15.9 wt%-Mass spectrometry (EI method) conditions; MS (m / e) 291 as in Example-1 [M-CH 3], 221 [M-C 3 H 6 OC 2 H 3], 207
[HSi (OSi (CH 3) 3) 2], 73 [(Si (CH 3) 3] · Nuclear magnetic resonance spectrum 1 HNMR chemical shift (ppm) TMS standard intensity ratio (a) 0.5 2 (b) 1.5 2 ( c) 3.5 2 (d) 3.8 1 (e) 4.1 1 (f) 6.3 1 example 3 CH 2 = CHOC 3 H 6 Si [OSi (CH 3) 3] 3 in the synthesis.
実施例１で用いた装置にアリルビニルエーテル672g（８
モル）、トルエン672g及びH2PtCl60.328gを仕込み、加
熱を開始して68℃でアリルビニルエーテルの還流が始ま
ったら滴下ロートよりトリストリメチルシロキシシラン
2.376g（10モル）の滴下を開始した。３時間で全量の滴
下を終了し、内温は110℃となった。滴下終了後１時間
還流を継続し、アリルビニルエーテルの消失を確認し
た。この合成液からイソプロピルアルコールを留去後,4
mmHg,93℃で減圧蒸留を行ない、純度97.5％の頭記合成
物質を1564g,収率51％で得た。672 g (8) of allyl vinyl ether was added to the apparatus used in Example 1.
Mol), 672 g of toluene and 0.328 g of H 2 PtCl 6 were added, and when heating started and reflux of allyl vinyl ether started at 68 ° C., tristrimethylsiloxysilane was added from the dropping funnel.
The addition of 2.376 g (10 mol) was started. The dropping of the entire amount was completed in 3 hours, and the internal temperature became 110 ° C. Refluxing was continued for 1 hour after completion of dropping, and disappearance of allyl vinyl ether was confirmed. After distilling off isopropyl alcohol from this synthetic solution, 4
By vacuum distillation at mmHg, 93 ° C., 1564 g of the above-mentioned synthetic substance having a purity of 97.5% was obtained with a yield of 51%.
構造の同定は元素分析、質量分析、核磁気共鳴スペクタ
ル（プロトン）により行なった。結果を以下に示す。The structure was identified by elemental analysis, mass spectrometry and nuclear magnetic resonance spectroscopy (proton). The results are shown below.
・元素分析 Si:29.5wt％,C:44.0wt％,H:9.4wt％,0:17.1wt％ ・質量分析（EI法） 条件；実施例−１の場合と同様 MS（m/e）365［Ｍ−CH3］,295［Ｍ−C3H6OC2H3］,207
［HSi（OSi（CH3）3)2］,73［（Si（CH3)3］ ・核磁気共鳴スペクトル1 HNMR ケミカルシフト（ppm）TMS基準 強度比 （ａ） 0.5 ２ （ｂ） 1.5 ２ （ｃ） 3.5 ２ （ｄ） 3.8 １ （ｅ） 4.1 １ （ｆ） 6.3 １ -Elemental analysis Si: 29.5 wt%, C: 44.0 wt%, H: 9.4 wt%, 0: 17.1 wt%-Mass spectrometry (EI method) conditions: MS (m / e) 365 as in Example-1 [M-CH 3], 295 [M-C 3 H 6 OC 2 H 3], 207
[HSi (OSi (CH 3) 3) 2], 73 [(Si (CH 3) 3] · Nuclear magnetic resonance spectrum 1 HNMR chemical shift (ppm) TMS standard intensity ratio (a) 0.5 2 (b) 1.5 2 ( c) 3.5 2 (d) 3.8 1 (e) 4.1 1 (f) 6.3 1
───────────────────────────────────────────────────── フロントページの続き (72)発明者 岡本 哲夫 東京都千代田区大手町２−６―１ 信越化 学工業株式会社内 (56)参考文献 特開 昭60−76580（ＪＰ，Ａ) ─────────────────────────────────────────────────── ─── Continuation of the front page (72) Inventor Tetsuo Okamoto 2-6-1 Otemachi, Chiyoda-ku, Tokyo Shin-Etsu Chemical Co., Ltd. (56) References JP-A-60-76580 (JP, A)
Claims (1)
3-n（ｎ＝0,1,2）で表されるビニロキシプロピルトリメ
チルシロキシシラン化合物。1. A general formula CH 2 = CHOC 3 H 6 Si (CH 3 ) n [OSi (CH 3 ) 3 ].
A vinyloxypropyltrimethylsiloxysilane compound represented by 3-n (n = 0,1,2).
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60220187A JPH0730092B2 (en) | 1985-10-04 | 1985-10-04 | Vinyloxypropyl trimethylsiloxysilane compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60220187A JPH0730092B2 (en) | 1985-10-04 | 1985-10-04 | Vinyloxypropyl trimethylsiloxysilane compound |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6281391A JPS6281391A (en) | 1987-04-14 |
| JPH0730092B2 true JPH0730092B2 (en) | 1995-04-05 |
Family
ID=16747243
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP60220187A Expired - Fee Related JPH0730092B2 (en) | 1985-10-04 | 1985-10-04 | Vinyloxypropyl trimethylsiloxysilane compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0730092B2 (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3914896A1 (en) * | 1989-05-05 | 1990-11-22 | Wacker Chemie Gmbh | ENOXY-FUNCTIONAL ORGANOSILICIUM COMPOUNDS, THEIR PRODUCTION AND USE |
| JP6335144B2 (en) * | 2015-07-02 | 2018-05-30 | 信越化学工業株式会社 | Polymerizable monomer and polymer thereof |
| JPWO2019239782A1 (en) * | 2018-06-14 | 2021-07-08 | 信越化学工業株式会社 | A method for producing a vinyl ether functional organopolysiloxane, a polymerizable composition and a cured product thereof. |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6076580A (en) * | 1983-10-04 | 1985-05-01 | Mitsui Petrochem Ind Ltd | Pretreatment agent composition for bonding |
-
1985
- 1985-10-04 JP JP60220187A patent/JPH0730092B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6281391A (en) | 1987-04-14 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| LAPS | Cancellation because of no payment of annual fees |