JPH0733783A - Silicon compound - Google Patents
Silicon compoundInfo
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- JPH0733783A JPH0733783A JP19789093A JP19789093A JPH0733783A JP H0733783 A JPH0733783 A JP H0733783A JP 19789093 A JP19789093 A JP 19789093A JP 19789093 A JP19789093 A JP 19789093A JP H0733783 A JPH0733783 A JP H0733783A
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- formula
- silicon compound
- compound
- silicon
- chemical
- 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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Abstract
Description
【０００１】[0001]
【産業上の利用分野】本発明は、特に有機ポリマーの変
性、改質に用いられる官能基を有するケイ素化合物への
変換、或いはシリコーン硬化組成物の架橋剤として有用
な新規なケイ素化合物に関する。FIELD OF THE INVENTION The present invention relates to a novel silicon compound which is particularly useful as a cross-linking agent for a silicone curing composition, or a conversion to a silicon compound having a functional group used for modifying or modifying an organic polymer.
【０００２】[0002]
【従来の技術及び発明が解決しようとする課題】従来よ
り、ケイ素原子に直接結合した水素原子を有するケイ素
化合物は、下記反応式に示されるように、不飽和基を有
する化合物と白金系化合物の触媒により容易に付加反応
するため、官能基を有するケイ素化合物、いわゆる現在
広範囲で使用されているカーボンファンクショナルシラ
ンの合成に用いられている有用なケイ素化合物である。2. Description of the Related Art Conventionally, a silicon compound having a hydrogen atom directly bonded to a silicon atom is a compound of an unsaturated group and a platinum compound as shown in the following reaction formula. It is a useful silicon compound used for the synthesis of a silicon compound having a functional group, that is, a so-called carbon functional silane which is widely used at present, because it easily undergoes an addition reaction with a catalyst.
【０００３】[0003]
【化２】 [Chemical 2]
【０００４】近年では、上述したような水素原子を有す
るシランやシロキサン、ポリシロキサンを用いて、官能
基を有する種々のポリシロキサンが開発、提案されてい
る。また、このような官能基を有するシラン、シロキサ
ン或いはポリシロキサンを用いることによって、それら
が有する化学反応性、熱的性質（耐寒性、耐熱性）や離
型性等の表面特性を利用して、有機ポリマーなどを変
性、改質することが試みられている。In recent years, various polysiloxanes having a functional group have been developed and proposed using silanes, siloxanes, and polysiloxanes having the above hydrogen atoms. Further, by using such a silane, siloxane, or polysiloxane having a functional group, the surface properties such as chemical reactivity, thermal properties (cold resistance, heat resistance), and mold release property of the silane, siloxane, or polysiloxane can be utilized, Attempts have been made to modify or modify organic polymers and the like.
【０００５】また、上述したような水素原子を有するシ
ロキサンオリゴマーは、ビニル基を含有するポリシロキ
サンと白金化合物とを組み合わせることにより、室温で
シロキサン硬化物を与える組成物（ＲＴＶ）の架橋剤と
して従来から用いられてきている。Further, the siloxane oligomer having a hydrogen atom as described above has hitherto been used as a crosslinking agent for a composition (RTV) which gives a siloxane cured product at room temperature by combining a vinyl group-containing polysiloxane and a platinum compound. Have been used since.
【０００６】本発明は、上記事情に鑑みなされたもの
で、有機ポリマーの変性や改質に使用される官能性を有
するケイ素化合物を合成する際の好適な中間体として、
或いは硬化性のシリコーン組成物の架橋剤として有用な
ビス−（ハイドロシロキシシリル）−アリレーン系の新
規なケイ素化合物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, and as a suitable intermediate for synthesizing a functional silicon compound used for modification or modification of an organic polymer,
Another object of the present invention is to provide a novel bis- (hydrosiloxysilyl) -arylene type silicon compound which is useful as a crosslinking agent for a curable silicone composition.
【０００７】[0007]
【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行った結果、下記一般
式（２）で示されるケイ素化合物と、下記式（３）或い
は下記式（４）で示されるケイ素化合物とを酸性条件下
で共加水分解することにより、下記一般式（１）で示さ
れる新規なケイ素化合物が得られ、該ケイ素化合物が芳
香族基や不飽和基との付加反応性に富む下記式（５）で
示される基を分子内に有しているため、有機ポリマーへ
の相溶性のある官能基を有するケイ素化合物の前駆体、
或いは室温硬化性シリコーン組成物の架橋剤、特にフェ
ニル変性シリコーン組成物に有用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 for Solving the Problems The present inventors have conducted diligent studies to achieve the above-mentioned object, and as a result, a silicon compound represented by the following general formula (2) and the following formula (3) or the following formula By co-hydrolyzing the silicon compound represented by (4) under acidic conditions, a novel silicon compound represented by the following general formula (1) is obtained, and the silicon compound is combined with an aromatic group or an unsaturated group. A precursor of a silicon compound having a functional group compatible with an organic polymer, since it has a group represented by the following formula (5) having high addition reactivity in the molecule,
Alternatively, it has been found that it is useful as a cross-linking agent for room temperature curable silicone compositions, especially for phenyl-modified silicone compositions,
The present invention has been completed.
【０００８】[0008]
【化３】 [Chemical 3]
【０００９】以下、本発明を更に詳述すると、本発明の
ケイ素化合物は、上述したように下記一般式（１）で示
されるものである。The present invention will be described in more detail below. The silicon compound of the present invention is represented by the following general formula (1) as described above.
【００１０】[0010]
【化４】 [Chemical 4]
【００１１】ここで、上記式（１）中の置換基Ｒ1とし
ては、例えばメチル基、エチル基、プロピル基、ブチル
基等の低級アルキル基が挙げられる。Examples of the substituent R 1 in the above formula (1) include lower alkyl groups such as methyl group, ethyl group, propyl group and butyl group.
【００１２】また、置換基Ｑとしては、下記式から選ば
れる二価の芳香族炭化水素基である。なお、ａは１〜３
の整数である。Further, the substituent Q is a divalent aromatic hydrocarbon group selected from the following formulas. Note that a is 1 to 3
Is an integer.
【００１３】[0013]
【化５】 [Chemical 5]
【００１４】このような式（１）で表されるケイ素化合
物の具体例としては、下記化合物（１ａ）〜（１ｄ）な
どを挙げることができる。Specific examples of the silicon compound represented by the formula (1) include the following compounds (1a) to (1d).
【００１５】[0015]
【化６】 [Chemical 6]
【００１６】上記式（１）のケイ素化合物は、下記一般
式（２）で示されるケイ素化合物と、下記式（３）或い
は（４）で示されるケイ素化合物とを酸性条件下で共加
水分解することにより合成することができる。The silicon compound of the above formula (1) cohydrolyzes the silicon compound represented by the following general formula (2) and the silicon compound represented by the following formula (3) or (4) under acidic conditions. It can be synthesized by
【００１７】[0017]
【化７】 （但し、式中Ｒ1，Ｑ，Ｘ，ａは上記と同様の意味を示
す。）[Chemical 7] (However, in the formula, R 1 , Q, X, and a have the same meanings as above.)
【００１８】この場合、上記式（２）の化合物として具
体的には、下記化合物などを挙げることができる。In this case, specific examples of the compound of the above formula (2) include the following compounds.
【００１９】[0019]
【化８】 [Chemical 8]
【００２０】上記式（２）の化合物は、対応するジハロ
ゲン化アリレーン化合物とケイ素化合物とからグリニャ
ール反応による公知の方法により合成することができ
る。例えば、（２ａ）式で示される化合物は、以下に示
す反応式により合成することができる。The compound of the above formula (2) can be synthesized from a corresponding dihalogenated arylene compound and a silicon compound by a known method by a Grignard reaction. For example, the compound represented by the formula (2a) can be synthesized by the reaction formula shown below.
【００２１】[0021]
【化９】 [Chemical 9]
【００２２】また、（３）式のケイ素化合物としては、
下記に示す化合物を例示することができる。Further, as the silicon compound represented by the formula (3),
The compound shown below can be illustrated.
【００２３】[0023]
【化１０】 [Chemical 10]
【００２４】なお、（２）式で表される化合物と、
（３）式又は（４）式で表される化合物との混合比は、
（２）式と（３）式との場合には、（２）式の化合物１
モルに対して（３）式の化合物を２ａ（但し、ａは上記
と同様の意味、即ち１〜３の整数を示す。）モル以上の
割合で用いることが好ましい。また、（２）式と（４）
式との場合には、（２）式の化合物１モルに対して、
（４）式の化合物をａモル以上の割合で用いることが好
ましい。A compound represented by the formula (2):
The mixing ratio with the compound represented by formula (3) or formula (4) is
In the case of the formulas (2) and (3), the compound 1 of the formula (2)
It is preferable to use the compound of the formula (3) in a ratio of 2a (where a is the same meaning as described above, that is, an integer of 1 to 3) mol or more with respect to mol. Also, equation (2) and (4)
In the case of formula, relative to 1 mol of the compound of formula (2),
It is preferable to use the compound of the formula (4) in a ratio of a mol or more.
【００２５】また、共加水分解に用いられる水の量は、
（２）式の化合物１モルに対して、２ａモル以上の割合
で用いることが好ましい。The amount of water used for co-hydrolysis is
It is preferable to use the compound of the formula (2) in an amount of 2 amol or more per 1 mol of the compound.
【００２６】更に、この共加水分解反応は、酸性条件下
で行うことが好ましく、（２）式の化合物と（３）式の
化合物との反応において、Ｘがハロゲン原子でない場合
には、用いる溶媒としては塩酸水溶液が好ましい。この
塩酸の量はごく微量で良いが、５〜２０重量％とするこ
とが好適である。Further, this cohydrolysis reaction is preferably carried out under acidic conditions, and when X is not a halogen atom in the reaction between the compound of formula (2) and the compound of formula (3), the solvent used. For this, an aqueous solution of hydrochloric acid is preferable. The amount of this hydrochloric acid may be very small, but is preferably 5 to 20% by weight.
【００２７】なお、加水分解反応条件は、２５℃以下、
特に１０℃以下で反応時間は４〜６時間とすることが好
ましい。また、反応溶媒は用いなくてもよいが、必要に
応じて、メタノール、エタノール、ジエチルエーテル、
プロピルエーテル、ヘキサン、トルエン、キシレン等の
溶媒を用いることができる。The hydrolysis reaction conditions are 25 ° C. or lower,
In particular, it is preferable that the reaction time is 10 ° C. or less and the reaction time is 4 to 6 hours. A reaction solvent may not be used, but if necessary, methanol, ethanol, diethyl ether,
Solvents such as propyl ether, hexane, toluene, xylene can be used.
【００２８】[0028]
【発明の効果】本発明のケイ素化合物は、分子内に芳香
族基や不飽和基と反応性の高いケイ素に結合した水素原
子を有するので、官能基を有する不飽和化合物との付加
反応に用いられ、有機ポリマーと相溶性のある変性、改
質剤の中間体として有用な化合物である。また、このケ
イ素化合物は、それ自身硬化の速いシリコーン硬化組成
物の架橋剤として有効な化合物でもある。INDUSTRIAL APPLICABILITY Since the silicon compound of the present invention has a hydrogen atom bonded to silicon, which has a high reactivity with an aromatic group or an unsaturated group, in the molecule, it is used for an addition reaction with an unsaturated compound having a functional group. It is a compound that is compatible with organic polymers and is useful as an intermediate for modifying and modifying agents. Further, this silicon compound is also a compound effective as a cross-linking agent for a silicone curing composition which cures itself quickly.
【００２９】[0029]
【実施例】以下、実施例を示し、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。EXAMPLES The present invention will be specifically described below with reference to examples, but the present invention is not limited to the following examples.
【００３０】［実施例１］ 〈４，４’−ビス−〔ジ−（ハイドロジエチル（シロキ
シ）−メチルシリル〕ジフェニルの合成方法〉フラスコ
に水７．８３ｇ、３５％濃塩酸１０．４４ｇを量り取
り、１０℃以下に冷却し、１０℃以下に保ちながら、ハ
イドロジメチルジシロキサン１０７．６ｇ（０．８モ
ル）を滴下する。次いで、同様に１０℃以下に保ちなが
ら、下記式（２ａ）で示される４，４’−ビス−（ジエ
トキシメチルシリル）−ジフェニルエーテル８３．６ｇ
（０．２モル）を滴下し、滴下後１５℃以下で６時間攪
拌を続けた。次いで、この反応液に５％硫酸ナトリウム
水溶液１００ｍｌとｎ−ヘキサン６０ｍｌとを加え、分
離した上層（有機層）を抽出し、この有機層を水１００
ｍｌで中性となるまで水洗を行う。この最終反応生成物
を減圧下２ｍｍＨｇ、１２０℃で低留分を除去し、無色
透明の液体１０１ｇ（収率９４％）を得た。得られた液
体については、次に示す分析結果より下記式（１ｂ）で
示される構造であることが確認された。[Example 1] <Method for synthesizing 4,4'-bis- [di- (hydrodiethyl (siloxy) -methylsilyl] diphenyl]> 7.83 g of water and 10.44 g of 35% concentrated hydrochloric acid were weighed into a flask. After cooling to 10 ° C. or lower, 107.6 g (0.8 mol) of hydrodimethyldisiloxane was added dropwise while keeping the temperature at 10 ° C. or lower, and then, similarly at 10 ° C. or lower, represented by the following formula (2a). 4,4'-bis- (diethoxymethylsilyl) -diphenyl ether 83.6 g
(0.2 mol) was added dropwise, and after the addition, stirring was continued at 15 ° C or lower for 6 hours. Next, 100 ml of a 5% aqueous sodium sulfate solution and 60 ml of n-hexane were added to this reaction solution, and the separated upper layer (organic layer) was extracted.
Rinse with water until neutral with ml. A low fraction was removed from this final reaction product at 120 ° C. under a reduced pressure of 2 mmHg to obtain 101 g (yield 94%) of a colorless transparent liquid. It was confirmed from the analysis results shown below that the obtained liquid had a structure represented by the following formula (1b).
【００３１】[0031]
【化１１】 屈折率（ｎ25 D） ： １．４８９ ＩＲ； ２９６０ｃｍ-1 Ｍ（Ｃ−Ｈ） ２１４０ｃｍ-1 Ｓ（Ｓｉ−Ｈ） １１１０〜１０００ｃｍ-1 Ｓ（Ｓｉ−Ｏ−Ｓｉ） ９０６ｃｍ-1 Ｓ（φ−Ｈ）1 Ｈ−ＮＭＲ（ＣＣｌ4）；δ（ｐｐｍ） ０．４３〜０．５３（Ｓｉ−ＣＨ3，ｍ，３０Ｈ） ４．８８〜５．１８（ＳｉＨ，ｍ，４Ｈ） ７．８（φＨ，ｓ，８Ｈ） Ｍ／Ｓ ｍ／ｅ ； ５３８（Ｍ+）[Chemical 11] Refractive index (n 25 D ): 1.489 IR; 2960 cm -1 M (C-H) 2140 cm -1 S (Si-H) 1110-1000 cm -1 S (Si-O-Si) 906 cm -1 S (φ -H) 1 H-NMR (CCl 4 ); δ (ppm) 0.43 to 0.53 (Si-CH 3 , m, 30H) 4.88 to 5.18 (SiH, m, 4H) 7.8. (ΦH, s, 8H) M / S m / e; 538 (M + )
【００３２】［実施例２］ 〈４，４’−ビス−〔ジ−（ハイドロジメチルシロキ
シ）−メチルシリル〕ジフェニルエーテルの合成〉水
７．８３ｇ、３５％濃塩酸１０．４４ｇ、ハイドロジメ
チルジシロキサン１０７．２ｇ（０．８モル）及び下記
式（２ｂ）で示される４，４’−ビス−（ジエトキシメ
チルシリル）−ジフェニルエーテル８６．８ｇ（０．２
モル）を用いた以外は実施例１と同様にして反応させ、
最終反応生成物を減圧下（２ｍｍＨｇ）１２０℃で低留
分を除去し、無色透明の液体１０２ｇ（収率９２％）を
得た。得られた液体については、下記に示す分析結果よ
り下記式（１ｃ）で示される構造であることが確認され
た。Example 2 Synthesis of 4,4'-bis- [di- (hydrodimethylsiloxy) -methylsilyl] diphenyl ether> 7.83 g of water, 10.44 g of 35% concentrated hydrochloric acid, 107. 2 g (0.8 mol) and 86.8 g (0.2) of 4,4′-bis- (diethoxymethylsilyl) -diphenyl ether represented by the following formula (2b).
Mol) was used and reacted in the same manner as in Example 1,
The low fraction was removed from the final reaction product at 120 ° C. under reduced pressure (2 mmHg) to obtain 102 g (yield 92%) of a colorless transparent liquid. It was confirmed from the analysis results shown below that the obtained liquid had a structure represented by the following formula (1c).
【００３３】[0033]
【化１２】 屈折率（ｎ25 D） ： １．４７８ ＩＲ； ２９６０ｃｍ-1 Ｍ（Ｃ−Ｈ） ２１４０ｃｍ-1 Ｓ（Ｓｉ−Ｈ） １１１０〜１０００ｃｍ-1 Ｓ（Ｓｉ−Ｏ−Ｓｉ） ９０６ｃｍ-1 Ｓ（φ−Ｈ）1 Ｈ−ＮＭＲ（ＣＣｌ4）；δ（ｐｐｍ） ０．３２〜０．４３（Ｓｉ−ＣＨ3，ｍ，３０Ｈ） ４．８〜５．０８（ＳｉＨ，ｍ，４Ｈ） ７．０７〜７．７３（φＨ，ｍ，８Ｈ） Ｍ／Ｓ ｍ／ｅ ； ５５４（Ｍ+）[Chemical 12] Refractive index (n 25 D ): 1.478 IR; 2960 cm -1 M (C-H) 2140 cm -1 S (Si-H) 1110-1000 cm -1 S (Si-O-Si) 906 cm -1 S (φ -H) 1 H-NMR (CCl 4 ); δ (ppm) 0.32 to 0.43 (Si-CH 3 , m, 30H) 4.8 to 5.08 (SiH, m, 4H) 7.07 ~ 7.73 (φH, m, 8H) M / S m / e; 554 (M + ).
【００３４】［実施例３］ 〈ビス｛ｐ−〔ジ−（ハイドロジメチルシロキシ）−メ
チルシリル〕−フェニル｝ジメチルシランの合成〉水
７．８３ｇ、３５％濃塩酸１０．４４ｇ、ハイドロジメ
チルジシロキサン１０７．２ｇ（０．８モル）及び下記
式（２ｃ）にで示されるビス｛ｐ−（ジエトキシメチル
シリル）フェニル｝ジメチルシラン９５．２ｇ（０．２
モル）を用いた以外は実施例１と同様にして反応させ、
最終反応生成物を減圧下（２ｍｍＨｇ）１２０℃で低留
分を除去し、無色透明の液体１１２ｇ（収率９４％）を
得た。得られた液体については、下記に示す分析結果よ
り下記式（１ｄ）で示される構造であることが確認され
た。[Example 3] <Synthesis of bis {p- [di- (hydrodimethylsiloxy) -methylsilyl] -phenyl} dimethylsilane> 7.83 g of water, 10.44 g of 35% concentrated hydrochloric acid, and hydrodimethyldisiloxane 107 .2 g (0.8 mol) and 95.2 g (0.2) of bis {p- (diethoxymethylsilyl) phenyl} dimethylsilane represented by the following formula (2c).
Mol) was used and reacted in the same manner as in Example 1,
A low fraction was removed from the final reaction product at 120 ° C. under reduced pressure (2 mmHg) to obtain 112 g of a colorless transparent liquid (yield 94%). It was confirmed from the analysis results shown below that the obtained liquid had a structure represented by the following formula (1d).
【００３５】[0035]
【化１３】 屈折率（ｎ25 D） ： １．４８１ ＩＲ； ２９６０ｃｍ-1 Ｍ（Ｃ−Ｈ） ２１４０ｃｍ-1 Ｓ（Ｓｉ−Ｈ） １１１０〜１０００ｃｍ-1 Ｓ（Ｓｉ−Ｏ−Ｓｉ） ９０６ｃｍ-1 Ｓ（φ−Ｈ）1 Ｈ−ＮＭＲ（ＣＣｌ4）；δ（ｐｐｍ） ０．４３〜０．７８（Ｓｉ−ＣＨ3，ｍ，３６Ｈ） ４．７５〜５．２（ＳｉＨ，ｍ，４Ｈ） ７．７５（φＨ，ｓ，４Ｈ） Ｍ／Ｓ ｍ／ｅ ； ５９６（Ｍ+）[Chemical 13] Refractive index (n 25 D ): 1.481 IR; 2960 cm -1 M (C-H) 2140 cm -1 S (Si-H) 1110-1000 cm -1 S (Si-O-Si) 906 cm -1 S (φ -H) 1 H-NMR (CCl 4 ); δ (ppm) 0.43 to 0.78 (Si-CH 3 , m, 36H) 4.75 to 5.2 (SiH, m, 4H) 7.75 (ΦH, s, 4H) M / S m / e; 596 (M + )
【００３６】次に、実施例１〜３で得られたケイ素化合
物０．１ｇをｎ−ブタノール３０ｍｌに溶解し、次いで
この溶液に２０％水酸化ナトリウム２０ｇを添加し、発
生する水素ガスを測定することにより、ケイ素に直接結
合する水素原子の量を評価した。Next, 0.1 g of the silicon compound obtained in Examples 1 to 3 is dissolved in 30 ml of n-butanol, 20 g of 20% sodium hydroxide is added to this solution, and the generated hydrogen gas is measured. By doing so, the amount of hydrogen atoms directly bonded to silicon was evaluated.
【００３７】[0037]
【化１４】 [Chemical 14]
【００３８】[0038]
【表１】 以上の結果より、測定値と理論値とが良く一致すること
が確認された。[Table 1] From the above results, it was confirmed that the measured value and the theoretical value are in good agreement.
Claims (1)
物。 【化１】 1. A silicon compound represented by the following general formula (1). [Chemical 1]
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP19789093A JP2806216B2 (en) | 1993-07-15 | 1993-07-15 | Silicon compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP19789093A JP2806216B2 (en) | 1993-07-15 | 1993-07-15 | Silicon compound |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH0733783A true JPH0733783A (en) | 1995-02-03 |
| JP2806216B2 JP2806216B2 (en) | 1998-09-30 |
Family
ID=16382000
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP19789093A Expired - Fee Related JP2806216B2 (en) | 1993-07-15 | 1993-07-15 | Silicon compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2806216B2 (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0786463A1 (en) * | 1996-01-25 | 1997-07-30 | Wacker-Chemie GmbH | Crosslinkable compositions |
| JP2010157689A (en) * | 2008-12-02 | 2010-07-15 | Shin-Etsu Chemical Co Ltd | ORGANIC SILANE COMPOUND FOR FORMING Si-CONTAINING FILM BY PLASMA CVD AND METHOD FOR FORMING Si-CONTAINING FILM |
| CN109384958A (en) * | 2018-10-19 | 2019-02-26 | 山东大学 | A kind of room temperature vulcanized silicone rubber crosslinking agent preparation method and applications |
-
1993
- 1993-07-15 JP JP19789093A patent/JP2806216B2/en not_active Expired - Fee Related
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0786463A1 (en) * | 1996-01-25 | 1997-07-30 | Wacker-Chemie GmbH | Crosslinkable compositions |
| JP2010157689A (en) * | 2008-12-02 | 2010-07-15 | Shin-Etsu Chemical Co Ltd | ORGANIC SILANE COMPOUND FOR FORMING Si-CONTAINING FILM BY PLASMA CVD AND METHOD FOR FORMING Si-CONTAINING FILM |
| US8546597B2 (en) | 2008-12-02 | 2013-10-01 | Shin-Etsu Chemical Co., Ltd | Organic silane compound for forming Si-containing film by plasma CVD and method for forming Si-containing film |
| CN109384958A (en) * | 2018-10-19 | 2019-02-26 | 山东大学 | A kind of room temperature vulcanized silicone rubber crosslinking agent preparation method and applications |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2806216B2 (en) | 1998-09-30 |
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