JPH08325274A - Organosilicon compound, its production and surface-treating agent - Google Patents
Organosilicon compound, its production and surface-treating agentInfo
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- JPH08325274A JPH08325274A JP15231495A JP15231495A JPH08325274A JP H08325274 A JPH08325274 A JP H08325274A JP 15231495 A JP15231495 A JP 15231495A JP 15231495 A JP15231495 A JP 15231495A JP H08325274 A JPH08325274 A JP H08325274A
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Abstract
Description
【０００１】[0001]
【産業上の利用分野】本発明は、種々の基材に撥水性、
撥油性を与えるための表面処理剤として有用な新規有機
けい素化合物、その製造方法、及びこの有機けい素化合
物を主剤とする表面処理剤に関する。BACKGROUND OF THE INVENTION The present invention is applied to various substrates for water repellency,
The present invention relates to a novel organic silicon compound useful as a surface treatment agent for imparting oil repellency, a method for producing the same, and a surface treatment agent containing the organic silicon compound as a main component.
【０００２】[0002]
【従来の技術及び発明が解決しようとする課題】従来、
分子内にフロロアルキル基と加水分解性シリル基を持つ
化合物としては、特開昭５８−１７２２４６号公報や特
開平４−１３６１８１号公報に示されるように以下の化
合物が代表例として知られている。2. Description of the Related Art Conventionally, the problems to be solved by the invention
As compounds having a fluoroalkyl group and a hydrolyzable silyl group in the molecule, the following compounds are known as typical examples, as shown in JP-A-58-172246 and JP-A-4-136181. .
【０００３】[0003]
【化４】 [Chemical 4]
【０００４】上記のようなフロロアルキル基を含み、加
水分解性シリル基を持つ化合物は、金属やガラス等の表
面処理剤として用いられているが種々の問題点がある。The compound containing a fluoroalkyl group and having a hydrolyzable silyl group as described above is used as a surface treatment agent for metals and glass, but has various problems.
【０００５】例えば、式（１）〜（３）の加水分解性基
としてハロゲノシリル基を持つ化合物は、金属等に処理
した場合、空気中の湿気で加水分解して塩酸ガスが発生
し、金属を腐食するという問題がある。For example, a compound having a halogenosilyl group as a hydrolyzable group of the formulas (1) to (3), when treated with a metal or the like, is hydrolyzed by moisture in the air to generate a hydrochloric acid gas, so that the metal is decomposed. There is a problem of corrosion.
【０００６】また、式（４）〜（６）の加水分解性基と
してアルコキシシリル基を持つ化合物は、金属、ガラス
等に処理した場合に加水分解速度が遅いため、充分な効
果が得られにくいという問題がある。さらに、式（７）
の化合物は撥水、撥油性を与える表面処理剤としての効
果は充分であるが、溶解する溶媒がｍ−キシレンヘキサ
フロライド等のフッ素系溶媒しかなく、一般的なベンゼ
ン、トルエン、キシレン、ヘキサン等に溶解しないとい
う欠点があった。Further, the compounds having an alkoxysilyl group as the hydrolyzable group of the formulas (4) to (6) have a slow hydrolysis rate when treated with a metal, glass, etc., and thus it is difficult to obtain a sufficient effect. There is a problem. Furthermore, equation (7)
The compound of 1 is sufficiently effective as a surface treatment agent for imparting water repellency and oil repellency, but the solvent to be dissolved is only a fluorinated solvent such as m-xylene hexafluoride, and general benzene, toluene, xylene, hexane. There was a drawback that it did not dissolve in etc.
【０００７】従って、上記式（１）〜（７）で示される
ような有機けい素化合物の持つ欠点を解決することが望
まれていた。Therefore, it has been desired to solve the drawbacks of the organic silicon compounds represented by the above formulas (1) to (7).
【０００８】[0008]
【課題を解決するための手段及び作用】本発明者は、上
記要望に応えるために鋭意検討を行った結果、下記一般
式（Ｂ）で表される化合物と下記一般式（Ｃ）で表され
る化合物とを脱塩化水素反応させることにより、分子内
にフロロアルキル基を含むと共に、加水分解性シリル基
としてジオルガノアミノシリル基を含む下記一般式
（Ａ）で表される新規有機けい素化合物が得られること
を見い出した。そして、この式（Ａ）の有機けい素化合
物が、従来知られている上記式（１）〜（７）で示され
るようなフロロアルキル基と加水分解性シリル基を持つ
有機けい素化合物の欠点を解決し得たものであり、加水
分解性に富み、かつ、フッ素系溶媒に溶解するのみでな
く、炭化水素系溶媒などの他の有機溶媒にも可溶であ
り、これを表面処理剤として使用した場合、優れた撥水
性及び撥油性を与えることを知見し、本発明をなすに至
ったものである。MEANS TO SOLVE THE PROBLEMS As a result of intensive studies to meet the above-mentioned demands, the present inventor has shown that a compound represented by the following general formula (B) and a compound represented by the following general formula (C). A novel organosilicon compound represented by the following general formula (A) containing a fluoroalkyl group in the molecule and a diorganoaminosilyl group as a hydrolyzable silyl group by dehydrochlorinating I found that The organosilicon compound of the formula (A) is a drawback of the conventionally known organosilicon compound having a fluoroalkyl group and a hydrolyzable silyl group as represented by the above formulas (1) to (7). It is possible to solve the problem, is rich in hydrolyzability, and is not only soluble in a fluorine-based solvent, it is also soluble in other organic solvents such as hydrocarbon-based solvent, this as a surface treatment agent The present inventors have found that it gives excellent water repellency and oil repellency when used, and have completed the present invention.
【０００９】[0009]
【化５】 （式中、Ｒ1 及びＲ2 は炭素数１〜６の１価炭化水素基
であり、Ｒ1 とＲ2 は互いに同一であっても異なってい
てもよい。ａは１，２又は３、ｎは０〜７の整数を示
す。）Embedded image (In the formula, R 1 and R 2 are monovalent hydrocarbon groups having 1 to 6 carbon atoms, and R 1 and R 2 may be the same or different from each other. A is 1, 2 or 3, n shows the integer of 0-7.)
【００１０】従って、本発明は、 ｉ 上記式（Ａ）の有機けい素化合物、 ii 上記式（Ｂ）の化合物と上記式（Ｃ）の化合物とを
脱塩化水素反応させることを特徴とする式（Ａ）の有機
けい素化合物の製造方法、 iii 上記式（Ａ）の有機けい素化合物を主剤とする表面
処理剤 を提供する。Therefore, the present invention is characterized in that i is an organosilicon compound of the above formula (A), ii is a compound of the above formula (B) and the above formula (C) is dehydrochlorinated. A method for producing an organic silicon compound of (A), iii A surface treatment agent containing an organic silicon compound of the above formula (A) as a main component.
【００１１】以下、本発明につき更に詳しく説明する。
本発明の新規有機けい素化合物は、下記一般式（Ａ）で
示されるものである。The present invention will be described in more detail below.
The novel organosilicon compound of the present invention is represented by the following general formula (A).
【００１２】[0012]
【化６】 [Chemical 6]
【００１３】ここで、Ｒ1 及びＲ2 は、互いに同一又は
異種の炭素数１〜６の１価炭化水素基であり、下記に示
すような直鎖状又は分枝状のアルキル基が好ましい。Here, R 1 and R 2 are the same or different monovalent hydrocarbon groups having 1 to 6 carbon atoms, and a linear or branched alkyl group as shown below is preferable.
【００１４】[0014]
【化７】 [Chemical 7]
【００１５】Ｒ1 及びＲ2 としては、これらの中で処理
後の揮発性の面からメチル基又はエチル基であることが
好ましい。ａは１，２又は３を示すが、特に２又は３で
あることが好ましい。ｎは０〜７の整数であり、好まし
くは７である。Of these, R 1 and R 2 are preferably a methyl group or an ethyl group from the viewpoint of volatility after treatment. a represents 1, 2 or 3, but 2 or 3 is particularly preferable. n is an integer of 0 to 7, preferably 7.
【００１６】上記式（Ａ）の有機けい素化合物の代表例
としては下記のものが例示され、これらの中で特にで
示されるものが好ましい。As typical examples of the organic silicon compound of the above formula (A), the following compounds are exemplified, and among these, those represented by are particularly preferable.
【００１７】[0017]
【化８】 Embedded image
【００１８】上記式（Ａ）の化合物は、下記一般式
（Ｂ）で表されるフロロアルキル基含有クロロシラン
と、下記一般式（Ｃ）で表わされるジオルガノアミンと
を脱塩化反応させることにより合成し得る。The compound of the above formula (A) is synthesized by dechlorinating a fluoroalkyl group-containing chlorosilane represented by the following general formula (B) and a diorganoamine represented by the following general formula (C). You can
【００１９】[0019]
【化９】 （Ｒ1 ，Ｒ2 ，ａ，ｎは上記と同様の意味を示す。）[Chemical 9] (R 1 , R 2 , a and n have the same meanings as above.)
【００２０】ここで、上記一般式（Ｂ）で示される化合
物の代表例として以下のものがあげられる。The following are typical examples of the compound represented by the above general formula (B).
【００２１】[0021]
【化１０】 [Chemical 10]
【００２２】また、一般式（Ｃ）で示される化合物の代
表例として以下のものがあげられる。The following are typical examples of the compound represented by the general formula (C).
【００２３】[0023]
【化１１】 [Chemical 11]
【００２４】上記式（Ｂ）のクロロシランと式（Ｃ）の
アミンとを反応させる場合、クロロシランのクロル原子
のモル数以上、好ましくは２モル以上のアミンを用い、
室温〜１２０℃程度で３０分〜１５時間程度反応させる
ことが好ましい。その際に、ジアルキルアミンを脱塩酸
剤としても良く、また、トリエチルアミンやピリジン等
の脱塩酸剤を添加しても良い。When the chlorosilane of the above formula (B) is reacted with the amine of the formula (C), the number of moles of the chloro atom of the chlorosilane is not less than, preferably not less than 2 moles,
The reaction is preferably carried out at room temperature to about 120 ° C. for about 30 minutes to 15 hours. At that time, a dialkylamine may be used as a dehydrochlorinating agent, or a dehydrochlorinating agent such as triethylamine or pyridine may be added.
【００２５】この反応の際の溶媒は使用しても良く、例
えばトルエン、キシレン等の芳香族系化合物やペンタ
ン、ヘキサン、オクタン、デカン等の炭化水素系化合物
等が好ましく、他の溶媒も可能であるが、活性水素を持
つ化合物は不適である。また、使用する溶媒は脱水して
から使用することが望ましい。A solvent for this reaction may be used, for example, aromatic compounds such as toluene and xylene and hydrocarbon compounds such as pentane, hexane, octane and decane are preferable, and other solvents are also possible. However, compounds having active hydrogen are not suitable. Further, it is desirable to dehydrate the solvent used before use.
【００２６】反応終了後、生成した塩酸塩は濾過により
分離しても良く、また、水洗して分離しても良い。水洗
する場合にはアルカリ水で洗浄することが好ましい。After completion of the reaction, the produced hydrochloride may be separated by filtration or washed with water. When washing with water, it is preferable to wash with alkaline water.
【００２７】本発明の式（Ａ）の化合物は種々の基材へ
の表面処理剤として有用であり、例えばガラスや鉄、ア
ルミ、銅、亜鉛等の金属、ポリエチレン、ポリプロピレ
ン、ポリエチレンテレフタレート、ポリカーボネート、
ナイロン等のプラスチックへ表面処理することで優れた
撥水性、撥油性を与え、これらの基材に耐水性や防汚性
を改良することができる。また、本化合物をガラス繊維
やマイカ、タルク、クレー、炭酸カルシウム、水酸化ア
ルミニウム、水酸化マグネシウム、酸化鉄、鉄、銅、ア
ルミニウム等の無機充填材に処理することで、これらの
充填材をフッ素系樹脂あるいはフッ素系ゴムに配合した
場合の機械的特性や耐水性、耐熱性を改良することがで
きる。The compound of the formula (A) of the present invention is useful as a surface treatment agent for various substrates, for example, glass, metals such as iron, aluminum, copper and zinc, polyethylene, polypropylene, polyethylene terephthalate, polycarbonate,
By subjecting plastics such as nylon to surface treatment, it is possible to impart excellent water repellency and oil repellency to improve the water resistance and stain resistance of these base materials. Further, by treating the present compound with an inorganic filler such as glass fiber, mica, talc, clay, calcium carbonate, aluminum hydroxide, magnesium hydroxide, iron oxide, iron, copper or aluminum, these fillers are treated with fluorine. It is possible to improve mechanical properties, water resistance, and heat resistance when compounded with a resin or a fluorine rubber.
【００２８】本発明の式（Ａ）の化合物を表面処理剤と
して用いる場合には、本化合物を適宜な溶媒に希釈して
使用することができる。この場合、希釈程度は、表面処
理剤中本化合物が０．０００１〜１０重量％濃度となる
ようにすることが好ましい。希釈溶媒としては、ペンタ
ン、ヘキサン等の脂肪族炭化水素系化合物、ベンゼン、
トルエン、キシレン等の芳香族炭化水素系化合物、ｍ−
キシレンヘキサフロライド等のフッ素系化合物、酢酸エ
チル等のエステル類、ジメチルホルムアミド等のアミド
類、ジエチルエーテル、ジブチルエーテル、テトラヒド
ロフラン、ジオキサン等のエーテル類等を用いることが
できる。When the compound of formula (A) of the present invention is used as a surface treating agent, the compound can be diluted with an appropriate solvent and used. In this case, the degree of dilution is preferably such that the present compound in the surface treatment agent has a concentration of 0.0001 to 10% by weight. As the diluent solvent, pentane, aliphatic hydrocarbon compounds such as hexane, benzene,
Aromatic hydrocarbon compounds such as toluene and xylene, m-
Fluorine compounds such as xylene hexafluoride, esters such as ethyl acetate, amides such as dimethylformamide, ethers such as diethyl ether, dibutyl ether, tetrahydrofuran, dioxane and the like can be used.
【００２９】本表面処理剤には本化合物に加え、他のシ
ラン系カップリング剤、チタネート系カップリング剤、
アルミニウム系カップリング剤、染料、顔料、酸化防止
剤、ＵＶ吸収剤、加水分解縮合触媒、防藻剤、防かび剤
等の添加剤を添加しても良い。In addition to the present compound, the present surface treating agent includes other silane coupling agents, titanate coupling agents,
Additives such as aluminum-based coupling agents, dyes, pigments, antioxidants, UV absorbers, hydrolysis-condensation catalysts, algae inhibitors and fungicides may be added.
【００３０】本表面処理剤の使用法は従来の表面処理剤
と同様でよく、例えば、基材に対して浸漬処理をしても
良く、スプレーによる塗布、ハケ塗り等によって処理し
ても良い。処理後は風乾するか、５０〜１５０℃程度で
乾燥しても良い。The surface treating agent may be used in the same manner as the conventional surface treating agent. For example, the substrate may be dipped, sprayed, brushed or the like. After the treatment, it may be air dried or dried at about 50 to 150 ° C.
【００３１】[0031]
【発明の効果】本発明の新規有機けい素化合物は、フッ
素系溶媒のみならず、炭化水素系溶媒にも溶解し、表面
処理剤として取り扱い性などの点で有利であり、また表
面処理剤として用いた場合、各種基材に優れた撥水性、
撥油性を与える。また、本発明の製造方法によれば、か
かる有機けい素化合物を簡単に製造することができる。The novel organosilicon compound of the present invention is soluble not only in a fluorine-based solvent but also in a hydrocarbon-based solvent and is advantageous as a surface treatment agent in terms of handleability, and also as a surface treatment agent. When used, it has excellent water repellency on various substrates,
Provides oil repellency. Further, according to the production method of the present invention, such an organic silicon compound can be easily produced.
【００３２】[0032]
【実施例】以下、実施例と比較例を示し、本発明を具体
的に説明するが、本発明は下記の実施例に制限されるも
のではない。EXAMPLES The present invention will be described below in detail with reference to examples and comparative examples, but the present invention is not limited to the following examples.
【００３３】〔実施例１〕攪拌機、温度計、還流冷却
器、ガス導入器をとりつけた１リットルセパラブルフラ
スコに式Ｃｌ3 Ｓｉ−（ＣＨ2 ）2 −（ＣＦ2 ）7 −Ｃ
Ｆ3 で表わされる化合物１９３．８ｇ（０．３３モル）
と脱水トルエン５００ｇを仕込み、これに２０℃にて
（ＣＨ3 ）2 ＮＨで示されるジメチルアミン１３５ｇ
（３モル）をガス導入器よりゆっくり導入した。導入に
は５時間を要した。導入終了時には３０℃まで温度は上
昇した。導入終了後、窒素バブリングを行ない、過剰の
ジメチルアミンを取りはぶき、濾過によりアミン塩酸塩
を取りはぶいた。その後、トルエンを留去したところ、
１８３．３ｇの微白濁の溶液が得られた。このものを蒸
留により精製したところ、無色透明な液体が１６２．６
ｇ得られた（収率８０．４％）。沸点は１２７℃／９ｍ
ｍＨｇであった。このものの赤外線吸収スペクトル分
析、 1Ｈ−核磁気共鳴スペクトル分析を行なった結果を
下記に記すが、これらの結果より｛（ＣＨ3）2Ｎ｝3Ｓ
ｉＣＨ2ＣＨ2（Ｃ Ｆ2）7ＣＦ3であることが確認でき
た。なお、このもののガスクロマトグラフ分析による純
度は９９．５％であった。 赤外線吸収スペクトル分析結果（図１） ２７９４ｃｍ-1 ： Ｎ−ＣＨ3 １２４３ｃｍ-1 ： Ｃ−Ｆ １２０６ｃｍ-1 ： Ｃ−Ｆ ９８７ｃｍ-1 ： Ｓｉ−Ｎ1 Ｈ−核磁気共鳴スペクトル分析結果（図２） 内標 ベンゼン δ＝７．２４ δ＝２．５１ｐｐｍ（ｓ，１８Ｈ）：Ｓｉ−Ｎ−ＣＨ3 δ＝０．７７〜１．１２ｐｐｍ（ｍ，２Ｈ）：Ｓｉ−Ｃ
Ｈ2 − δ＝１．６６〜２．４３ｐｐｍ（ｍ，２Ｈ）：Ｓｉ−Ｃ
Ｈ2 −ＣＨ2 [Example 1] Stirrer, thermometer, reflux cooling
1 liter separable hula with gas and gas inlet
The formula Cl3Si- (CH2)2-(CF2)7-C
F3Compound represented by 193.8 g (0.33 mol)
And 500 g of dehydrated toluene were charged, and at 20 ° C.
(CH3)2135 g of dimethylamine represented by NH
(3 mol) was slowly introduced from the gas introducer. For introduction
Took 5 hours. At the end of the introduction, the temperature will rise to 30 ° C.
I have risen. After the introduction was completed, nitrogen bubbling was performed to
Remove dimethylamine and filter to obtain amine hydrochloride.
I got rid of it. After that, when toluene was distilled off,
183.3 g of a slightly cloudy solution was obtained. Steam this one
When purified by distillation, a colorless transparent liquid was found to be 162.6.
g was obtained (yield 80.4%). Boiling point is 127 ° C / 9m
It was mHg. Infrared absorption spectrum of this product
Analysis,1The result of H-nuclear magnetic resonance spectrum analysis
As shown below, from these results {(CH3)2N}3S
iCH2CH2(C F2)7CF3Can be confirmed
Was. In addition, pure gas analysis of this product
The degree was 99.5%. Infrared absorption spectrum analysis result (Fig. 1) 2794 cm-1 : N-CH3 1243 cm-1 : C-F 1206 cm-1 : C-F 987 cm-1 : Si-N1 H-nuclear magnetic resonance spectrum analysis result (FIG. 2) Internal standard Benzene δ = 7.24 δ = 2.51 ppm (s, 18H): Si-N-CH 3 δ = 0.77 to 1.12 ppm (m, 2H): Si-C
H 2 -? = 1.66 to 2.43 ppm (m, 2H): Si-C
H2−CH 2
【００３４】〔実施例２〜４、比較例１〜３〕実施例１
と同様な装置またはガス導入器を滴下装置に代えたもの
を用いて表１に示す原料ａ，ｂを反応させ、その後の操
作は同様にして、表１に示す生成物を得た。なお、これ
らの生成物は、赤外線吸収スペクトル分析及び 1Ｈ−核
磁気共鳴スペクトル分析により構造を確認した。[Examples 2 to 4, Comparative Examples 1 to 3] Example 1
The raw materials a and b shown in Table 1 were reacted using an apparatus similar to the above or a gas introducing device instead of the dropping apparatus, and the subsequent operation was performed in the same manner to obtain the products shown in Table 1. The structures of these products were confirmed by infrared absorption spectrum analysis and 1 H-nuclear magnetic resonance spectrum analysis.
【００３５】[0035]
【表１】 [Table 1]
【００３６】実施例１〜４にて合成した化合物及び下記
式で示される比較例の化合物の溶媒への溶解性を表２に
示した。The solubilities of the compounds synthesized in Examples 1 to 4 and the compounds of Comparative Examples represented by the following formulas in solvents are shown in Table 2.
【００３７】[0037]
【化１２】 [Chemical 12]
【００３８】[0038]
【表２】 [Table 2]
【００３９】表２から明らかなように、本化合物は芳香
族系炭化水素系及び脂肪族系炭化水素に任意の濃度で溶
解することが確認された。これは比較例３の化合物と大
きく異なる特性であった。As is clear from Table 2, it was confirmed that this compound is soluble in aromatic hydrocarbon and aliphatic hydrocarbons at any concentration. This was a characteristic that was significantly different from the compound of Comparative Example 3.
【００４０】〔実施例５〜８、比較例４〜５〕実施例１
〜４にて合成した化合物及び比較例１，２の化合物を２
％ヘキサン溶液に調整し、本発明の実施例５〜８の表面
処理剤及び比較例４，５の表面処理剤とした。また、比
較例３の化合物はｍ−キシレンヘキサフロライドに２％
溶解し、比較例６の表面処理剤とした。これらの表面処
理剤中に清浄なガラス板を浸漬し、風乾し、表面処理ガ
ラス板を得た。このガラス板の水の接触角及びヘキサデ
カンの接触角を測定した結果を表３に示す。[Examples 5 to 8 and Comparative Examples 4 to 5] Example 1
2 and the compounds synthesized in Comparative Examples 1 and 2
% Hexane solution to prepare the surface treatment agent of Examples 5 to 8 of the present invention and the surface treatment agent of Comparative Examples 4 and 5. Further, the compound of Comparative Example 3 contained 2% of m-xylene hexafluoride.
It melt | dissolved and it was set as the surface treatment agent of the comparative example 6. A clean glass plate was immersed in these surface treatment agents and air-dried to obtain a surface-treated glass plate. The results of measuring the contact angle of water and the contact angle of hexadecane on this glass plate are shown in Table 3.
【００４１】表３から明らかなように、本発明の化合物
で処理されたガラス板は、撥水、撥油性の表面に改質さ
れていることが確認できた。As is clear from Table 3, it was confirmed that the glass plate treated with the compound of the present invention was modified to have a water-repellent and oil-repellent surface.
【００４２】[0042]
【表３】 [Table 3]
【図１】実施例１で合成された化合物の赤外線吸収スペ
クトルである。1 is an infrared absorption spectrum of the compound synthesized in Example 1. FIG.
【図２】実施例１で合成された化合物の 1Ｈ−核磁気共
鳴スペクトルである。FIG. 2 is a 1 H-nuclear magnetic resonance spectrum of the compound synthesized in Example 1.
Claims (3)
であり、Ｒ1 とＲ2 は互いに同一であっても異なってい
てもよい。ａは１，２又は３、ｎは０〜７の整数を示
す。）で表される有機けい素化合物。1. The following general formula (A): (In the formula, R 1 and R 2 are monovalent hydrocarbon groups having 1 to 6 carbon atoms, and R 1 and R 2 may be the same or different from each other. A is 1, 2 or 3, n represents an integer of 0 to 7.) An organic silicon compound represented by the formula.
す。）で表される化合物と、下記一般式（Ｃ） 【化３】 （式中、Ｒ1 及びＲ2 は炭素数１〜６の１価炭化水素基
であり、Ｒ1 とＲ2 は互いに同一であっても異なってい
てもよい。）で表される化合物とを脱塩化水素反応させ
ることを特徴とする請求項１記載の有機けい素化合物の
製造方法。2. The following general formula (B): (In the formula, a is 1, 2, or 3, and n is an integer of 0 to 7), and a compound represented by the following general formula (C): (In the formula, R 1 and R 2 are monovalent hydrocarbon groups having 1 to 6 carbon atoms, and R 1 and R 2 may be the same or different from each other.) Dehydrochlorination reaction is carried out, The manufacturing method of the organosilicon compound of Claim 1 characterized by the above-mentioned.
とする表面処理剤。3. A surface treatment agent containing the organosilicon compound according to claim 1 as a main component.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP15231495A JP3558099B2 (en) | 1995-05-26 | 1995-05-26 | Organosilicon compound, method for producing the same, and surface treating agent |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP15231495A JP3558099B2 (en) | 1995-05-26 | 1995-05-26 | Organosilicon compound, method for producing the same, and surface treating agent |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH08325274A true JPH08325274A (en) | 1996-12-10 |
| JP3558099B2 JP3558099B2 (en) | 2004-08-25 |
Family
ID=15537821
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP15231495A Expired - Fee Related JP3558099B2 (en) | 1995-05-26 | 1995-05-26 | Organosilicon compound, method for producing the same, and surface treating agent |
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| Country | Link |
|---|---|
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7045170B1 (en) | 2002-04-03 | 2006-05-16 | Sandia Corporation | Anti-stiction coating for microelectromechanical devices |
-
1995
- 1995-05-26 JP JP15231495A patent/JP3558099B2/en not_active Expired - Fee Related
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7045170B1 (en) | 2002-04-03 | 2006-05-16 | Sandia Corporation | Anti-stiction coating for microelectromechanical devices |
Also Published As
| Publication number | Publication date |
|---|---|
| JP3558099B2 (en) | 2004-08-25 |
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