JP4453827B2 - Organoxysilane compound having siloxane bond and method for producing the same - Google Patents

Description

  The present invention relates to an organoxysilane compound having a siloxane bond that is useful as a water-repellent treatment agent for glass or metal surfaces, a polymer modifier, a silylating agent, and the like, and a method for producing the same.

  It is known that glass or metal surfaces are treated with an organosilicon compound to impart water repellency to each surface. Conventionally, as the water repellent treatment agent, for example, alkylpolysiloxane compounds described in JP-B-50-15473 (Patent Document 1) and JP-B-63-67828 (Patent Document 2) have been used. However, when the above alkylpolysiloxane compound is used, the water repellency is not sufficient (the contact angle of the water droplet is small, the value of the falling angle is large, that is, the water droplet is difficult to slip), and the weather resistance and durability are inferior. There is a problem.

  As a water repellent treatment agent with improved weather resistance and durability, “Silicone Handbook” (by Nikkan Kogyo Shimbun, Kunio Ito) p. 79, 9th line-p. Examples thereof include the alkylorganoxysilane compounds and fluoroalkylorganoxysilane compounds described in the 80th and 5th lines. Since these compounds are obtained by partially hydrolyzing and condensing organoxysilane compounds as water repellent treatment agents, they can be strongly bonded to hydroxyl groups on the surface of glass or the like using covalent bonds, and are resistant to weathering and sustained. Has been improved.

  However, when an alkylorganoxysilane compound is used, the above water repellency (contact angle, sliding angle) is still not sufficient. In addition, although the water repellency of the fluoroalkylorganoxysilane compound is improved, it is expensive and insoluble in general solvents, so it is an expensive and special fluorine-based solvent as a water repellent. There is a problem that a solvent must be used, which is expensive and burdens the environment.

Japanese Patent Publication No. 50-15473 Japanese Patent Publication No. 63-67828 “Silicone Handbook”, Nikkan Kogyo Shimbun, Kunio Ito, p. 79, 9th line-p. 80, 5th line

  The present invention has been made in view of the above circumstances, an organoxysilane compound having a siloxane bond that has weather resistance and durability, is soluble in general solvents, and can impart high water repellency, and the production thereof It aims to provide a method.

As a result of intensive studies to achieve the above object, the present inventor has found that the following general formula (1)
_{^{(R 1) n Si {OSi}} (CH 3) m (OR 2) 3-m} 4-n (1)
Wherein R ¹ is the same or different monovalent hydrocarbon group having 1 to 10 carbon atoms, at least one is a branched alkyl group having 3 to 10 carbon atoms, and R ² is 1 having 1 to 10 carbon atoms. Valent hydrocarbon group, m is 0 or 1 , and n is 1, 2 or 3.)
The organoxysilane compound having a siloxane bond represented by is soluble in a general solvent and has excellent weather resistance and durability when used as a water-repellent treatment agent for glass and metal surfaces, and has higher water repellency. It has been found that the compound can be imparted, and that the novel compound is also useful as a polymer modifier or silylating agent capable of introducing siloxane, and the present invention has been completed.

（式中、Ｒ²、ｍは上記と同様であり、Ｒ³、Ｒ⁴は水素原子又は炭素数１〜１０の１価炭化水素基、Ｒ⁵は炭素数１〜１０の１価炭化水素基である。）
で示されるシリルケテンアセタール化合物とを酸触媒存在下に反応させることを特徴とする［Ｉ］のシロキサン結合を有するオルガノキシシラン化合物の製造方法。
［Ｖ］ 下記一般式（２）
（Ｒ¹）_nＳｉ（ＯＨ）_4-n （２）
（式中Ｒ¹、ｎは上記と同様である。）
で示されるシラノール化合物と、下記一般式（４）
Ｓｉ（ＣＨ₃）_m（ＯＲ²）_4-m （４）
（式中、Ｒ²、ｍは上記と同様である。）
で示されるオルガノキシシラン化合物とを触媒存在下に反応させることを特徴とする［Ｉ］のシロキサン結合を有するオルガノキシシラン化合物の製造方法。 Accordingly, the present invention provides the following silane compound and a method for producing the same.
[I] The following general formula (1)
_{^{(R 1) n Si {OSi}} (CH 3) m (OR 2) 3-m} 4-n (1)
Wherein R ¹ is the same or different monovalent hydrocarbon group having 1 to 10 carbon atoms, at least one is a branched alkyl group having 3 to 10 carbon atoms, and R ² is 1 having 1 to 10 carbon atoms. Valent hydrocarbon group, m is 0 or 1 , and n is 1, 2 or 3.)
An organoxysilane compound having a siloxane bond represented by
[II] The organoxysilane compound having a siloxane bond according to [I], wherein the branched alkyl group is selected from an isopropyl group, an isobutyl group, a t-butyl group, and a texyl group.
[ III ] The organoxysilane compound having a siloxane bond represented by the general formula (1) is t-butyldimethylsiloxytrimethoxysilane, t-butyldimethylsiloxytriethoxysilane, triisopropylsiloxytrimethoxysilane, or triisopropylsiloxy. An organoxysilane compound having a siloxane bond of [I] or [II] which is triethoxysilane.
[ IV ] The following general formula (2)
(R ¹ ) _n Si (OH) _4-n (2)
(Wherein R ¹ and n are the same as described above.)
And a silanol compound represented by the following general formula (3)

(Wherein R ² and m are the same as above, R ³ and R ⁴ are hydrogen atoms or monovalent hydrocarbon groups having 1 to 10 carbon atoms, and R ⁵ is a monovalent hydrocarbon group having 1 to 10 carbon atoms. .)
A process for producing an organoxysilane compound having a siloxane bond according to [I], wherein the silyl ketene acetal compound represented by formula (I) is reacted in the presence of an acid catalyst.
[ V ] The following general formula (2)
(R ¹ ) _n Si (OH) _4-n (2)
(Wherein R ¹ and n are the same as described above.)
And the following general formula (4)
Si (CH ₃ ) _m (OR ² ) _4-m (4)
(In the formula, R ² and m are the same as above.)
A process for producing an organoxysilane compound having a siloxane bond according to [I], wherein the organoxysilane compound represented by formula (I) is reacted in the presence of a catalyst.

  According to the present invention, when an organoxysilane compound having a siloxane bond is used as a water repellent treatment agent, it is superior in weather resistance and sustainability compared with conventional water repellent treatment agents, and can impart higher water repellency. . This novel compound is also useful as a polymer modifier or silylating agent capable of introducing siloxane.

The compound of the present invention is an organoxysilane compound represented by the following general formula (1).
_{^{(R 1) n Si {OSi}} (CH 3) m (OR 2) 3-m} 4-n (1)
Wherein R ¹ is the same or different monovalent hydrocarbon group having 1 to 10 carbon atoms, at least one is a branched alkyl group having 3 to 10 carbon atoms, and R ² is 1 having 1 to 10 carbon atoms. Valent hydrocarbon group, m is 0 or 1 , and n is 1, 2 or 3.)

In this case, examples of the monovalent hydrocarbon group represented by R ¹ and R ^{2 in} the general formula (1) include linear, branched or cyclic alkyl groups, alkenyl groups, aryl groups, aralkyl groups, and the like. ^{If 1} is a monovalent hydrocarbon group having 2 or less carbon atoms, the water repellency is inferior.

As the alkyl group, methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, t-butyl group, pentyl group, cyclopentyl group, hexyl group, cyclohexyl group, texyl group, octyl group, decyl group, norbornyl Groups and the like.
Examples of the alkenyl group include a vinyl group, an allyl group, a propenyl group, a butenyl group, a hexenyl group, a cyclohexenyl group, and a norbornyl group.
Examples of the aryl group include a phenyl group, a tolyl group, a xylyl group, and a naphthyl group.
Examples of the aralkyl group include a benzyl group, a phenylethyl group, and a phenylpropyl group.

R ² is particularly preferably an alkyl group, particularly 1 to 6, more preferably 1 to 4.

Organoxysilane compound of the present invention specifically with isopropyl dimethylsiloxy trimethoxy silane, isopropyl dimethylsiloxy methyl dimethoxy silane, Lee Seo butyldimethylsiloxy trimethoxysilane, isobutyl butyldimethylsiloxymethyl dimethoxysilane, t - butyl dimethylsiloxy trimethoxysilane, t- butyl dimethylsiloxy methyl dimethoxy silane, Application Benefits isopropyl siloxy trimethoxy silane, triisopropylsiloxy methyl dimethoxy silane, Te hexyl dimethylsiloxy trimethoxysilane, thexyldimethylsilyl dimethylsiloxy methyl dimethoxysilane, t - butyldiphenylsiloxy tri silane, t- butyl butyldiphenylsiloxy methyl dimethoxysilane, t - butyl methyl bis (trimethoxysiloxy Silane, t- butyl methyl bis (methyl-dimethoxy) silane, Te hexyl methyl bis (trimethoxy) silane, thexyl methyl bis (methyl-dimethoxy) silane, t - Buchirutorisu (trimethoxy) silane, t-Buchirutorisu ( methyl dimethoxy) silane, Te Kishirutorisu (trimethoxy) silane, Tekishirutorisu (methyl dimethoxy) silane, with isopropyl dimethylsiloxy triethoxysilane, isopropyl dimethylsiloxy methyl diethoxy silane, Lee Seo butyldimethylsiloxy triethoxysilane, isobutyl dimethylsiloxy methyl diethoxy silane, t - butyl dimethylsiloxy triethoxysilane, t- butyl dimethylsiloxy methyl diethoxy silane, preparative Riiso Propyl siloxy triethoxysilane, triisopropylsiloxy methyl diethoxy silane, Te hexyl dimethylsiloxy triethoxysilane, thexyldimethylsilyl dimethylsiloxy methyl diethoxy silane, t - butyldiphenylsiloxy triethoxysilane, t- butyl butyldiphenylsiloxy methyl diethoxy silane, t - butyl methyl bis (triethoxy siloxy) silane, t- butyl methyl bis (methyl diethoxy) silane, Te hexyl methyl bis (triethoxy siloxy) silane, thexyl methyl bis (methyl diethoxy) silane, t - Buchirutorisu (triethoxy) silane, t-Buchirutorisu (methyl diethoxy) silane, Te Kishirutorisu (triethoxy) silane, Tekishirutorisu (Mechirujietoki Siloxy) and Sila down, preferably of the above compounds, R ¹ is any 3 or more carbon atoms, and / or at least one of R ¹ is a compound which is branched alkyl group, more preferably t- butyl Dimethylsiloxytrimethoxysilane, t-butyldimethylsiloxytriethoxysilane, triisopropylsiloxytrimethoxysilane, and triisopropylsiloxytriethoxysilane.

（式中、Ｒ²、ｍは上記と同様、Ｒ³、Ｒ⁴は水素原子又は炭素数１〜１０の１価炭化水素基、Ｒ⁵は炭素数１〜１０の１価炭化水素基である。）
で示されるシリルケテンアセタール化合物とを酸触媒存在下に反応させる方法が例示される。
ここで、Ｒ³〜Ｒ⁵の１価炭化水素基としては、Ｒ¹、Ｒ²と同様のものが例示される。 Moreover, the manufacturing method of the organoxysilane compound shown by the said General formula (1) in this invention is the following General formula (2), for example.
(R ¹ ) _n Si (OH) _4-n (2)
(In the formula, R ¹ and n are the same as above.)
And a silanol compound represented by the following general formula (3)

(Wherein R ² and m are the same as above, R ³ and R ⁴ are a hydrogen atom or a monovalent hydrocarbon group having 1 to 10 carbon atoms, and R ⁵ is a monovalent hydrocarbon group having 1 to 10 carbon atoms. .)
The method of making it react with the silyl ketene acetal compound shown by the presence of an acid catalyst is illustrated.
Here, examples of the monovalent hydrocarbon group represented by R ^{3 to} R ⁵ include the same groups as R ¹ and R ² .

The silanol compound represented by the general formula (2), in particular with isopropyl dimethylsilanol, Lee Seo-butyldimethylsilanol, t - butyl dimethyl silanol, triisopropyl silanol, thexyldimethylsilyl silanol, t - butyl diphenyl silanol , t - butyl methyl disilanol, thexyldimethylsilyl methyl disilanol, t- butyl trisilanol, thexyldimethylsilyl tri silanol Lumpur like.

  Moreover, the silyl ketene acetal compound shown by the said General formula (3) used by the said reaction can be manufactured by reaction of the unsaturated carboxylic acid ester and hydrogen silane compound of patent 3009327 gazette.

Specific examples of the silyl ketene acetal compound include 1-trimethoxysiloxy-1-methoxy-1-propene, 1-methyldimethoxysiloxy-1-methoxy-1-propene , and 1 -trimethoxysiloxy-1-ethoxy- 1-propene, 1-methyldimethoxysiloxy-1-ethoxy-1-propene , 1 -trimethoxysiloxy-1-butoxy-1-propene, 1-methyldimethoxysiloxy-1-butoxy-1-propene , 1 -trimethoxy Siloxy-1- (2-ethyl-1-hexyloxy) -1-propene, 1-methyldimethoxysiloxy-1- (2-ethyl-1-hexyloxy) -1-propene , 1 -triethoxysiloxy-1-methoxy- 1-propene, 1-diethoxy-siloxy-1-methoxy-1-propene, 1 Triethoxysiloxy-1-ethoxy-1-propene, 1-diethoxy-siloxy-1-ethoxy-1-propene, 1 - triethoxysiloxy-1-butoxy-1-propene, 1-diethoxy-siloxy-1 Butoxy-1-propene , 1 -triethoxysiloxy-1- (2-ethyl-1-hexyloxy) -1-propene, 1-methyldiethoxysiloxy-1- (2-ethyl-1-hexyloxy) -1-prop Are exemplified.

  The compounding ratio of the silanol compound represented by the general formula (2) and the silyl ketene acetal compound represented by the general formula (3) is not particularly limited, but from the viewpoint of reactivity and productivity, 1 mol of the silanol compound is used. On the other hand, a range of 0.5 to 2 mol, particularly 0.8 to 1.2 mol, of the silyl ketene acetal compound is preferable.

  Specific examples of the acid catalyst used in the above reaction include hydrochloric acid, sulfuric acid, methanesulfonic acid, benzenesulfonic acid, p-toluenesulfonic acid, trifluoromethanesulfonic acid, and trifluoroacetic acid.

  Although the usage-amount of an acid catalyst is not specifically limited, From the point of reactivity and productivity, the range of 0.0001-0.1 mol, especially 0.001-0.05 mol with respect to 1 mol of silanol groups of a silanol compound. Is preferred.

  Although the reaction temperature of the said reaction is not specifically limited, 0-120 degreeC, Especially 10-100 degreeC is preferable.

  In addition, although the said reaction advances even without a solvent, a solvent can also be used. Solvents used include hydrocarbon solvents such as pentane, hexane, cyclohexane, heptane, isooctane, benzene, toluene and xylene, ether solvents such as diethyl ether, tetrahydrofuran and dioxane, and ester solvents such as ethyl acetate and butyl acetate. And aprotic polar solvents such as acetonitrile and N, N-dimethylformamide, and chlorinated hydrocarbon solvents such as dichloromethane and chloroform. These solvents may be used alone or in combination of two or more.

Moreover, as a manufacturing method of the organoxysilane compound shown by the said General formula (1) in this invention, following General formula (2)
(R ¹ ) _n Si (OH) _4-n (2)
(Wherein R ¹ , R ² and n are the same as above)
And the following general formula (4)
Si (CH ₃ ) _m (OR ² ) _4-m (4)
(In the formula, R ² and m are the same as above.)
A method of reacting an organoxysilane compound represented by the above in the presence of a catalyst is also exemplified.

  Specific examples of the organoxysilane compound represented by the general formula (4) include tetramethoxysilane, methyltrimethoxysilane, dimethyldimethoxysilane, tetraethoxysilane, methyltriethoxysilane, and dimethyldiethoxysilane. The

  The compounding ratio of the silanol compound represented by the general formula (2) and the organoxysilane compound represented by the general formula (4) is not particularly limited, but from the viewpoint of reactivity and productivity, 1 mol of the silanol compound is used. On the other hand, the range of 0.5 to 2 mol, particularly 0.8 to 1.2 mol of the organoxysilane compound is preferable.

  Specific examples of the catalyst used in the above reaction include hydrochloric acid, sulfuric acid, methanesulfonic acid, benzenesulfonic acid, p-toluenesulfonic acid, trifluoromethanesulfonic acid, trifluoroacetic acid and other acid catalysts, sodium methoxide, Examples include base catalysts such as sodium ethoxide, sodium hydroxide, potassium hydroxide, and tetraalkylammonium hydroxide.

The amount of the catalyst used is not particularly limited, but from the viewpoint of reactivity and productivity, the range of 0.0001 to 0.1 mol, particularly 0.001 to 0.05 mol, relative to 1 mol of silanol groups of the silanol compound. preferable.
Although the reaction temperature of the said reaction is not specifically limited, 0-120 degreeC, Especially 10-100 degreeC is preferable.

  In addition, although the said reaction advances even without a solvent, a solvent can also be used. Solvents used include hydrocarbon solvents such as pentane, hexane, cyclohexane, heptane, isooctane, benzene, toluene and xylene, ether solvents such as diethyl ether, tetrahydrofuran and dioxane, and ester solvents such as ethyl acetate and butyl acetate. And aprotic polar solvents such as acetonitrile and N, N-dimethylformamide, chlorinated hydrocarbon solvents such as dichloromethane and chloroform, alcohol solvents such as methanol and ethanol, and the like. These solvents may be used alone or in combination of two or more.

  EXAMPLES Hereinafter, although an Example and a comparative example are shown and this invention is demonstrated concretely, this invention is not restrict | limited to the following Example.

Example 1 t-Butyldimethylsiloxytrimethoxysilane Into a flask equipped with a stirrer, a reflux condenser, a dropping funnel and a thermometer, 104.2 g of 1-trimethoxysiloxy-1-methoxy-1-propene (0.5%) was added. Mol) and 0.48 g (0.005 mol) of methanesulfonic acid were charged and heated to 50 ° C. After the internal temperature was stabilized, 66.2 g (0.5 mol) of t-butyldimethylsilanol was added dropwise over 2 hours and stirred at that temperature for 1 hour. The reaction solution was distilled to obtain 98.1 g of a fraction having a boiling point of 83 to 84 ° C./2 kPa.
A mass spectrum, ¹ H-NMR spectrum, and IR spectrum of the obtained fraction were measured.

<Mass spectrum>
m / z 237, 195, 165, 135, 119, 105
¹ H-NMR spectrum (deuterated chloroform solvent): FIG. 1 shows a chart.
IR spectrum: shown as a chart in FIG.
From the above results, it was confirmed that the obtained compound was t-butyldimethylsiloxytrimethoxysilane.

[ Reference Example 1 ] Triphenylsiloxytrimethoxysilane 104.2 g (0.5 mol) of 1-trimethoxysiloxy-1-methoxy-1-propene was added to a flask equipped with a stirrer, a reflux condenser, a dropping funnel and a thermometer. Then, 0.48 g (0.005 mol) of methanesulfonic acid was charged and heated to 50 ° C. After the internal temperature was stabilized, a solution of 138.2 g (0.5 mol) of triphenylsilanol in tetrahydrofuran (138.2 g) was added dropwise over 2 hours and stirred at 80 ° C. for 7 hours. The reaction solution was distilled to obtain 172.9 g of a fraction having a boiling point of 153-155 ° C./10 Pa.
A mass spectrum, ¹ H-NMR spectrum, and IR spectrum of the obtained fraction were measured.

<Mass spectrum>
m / z 396, 319, 289, 227, 181, 151
¹ H-NMR spectrum (deuterated chloroform solvent): shown in the chart of FIG.
IR spectrum: shown in the chart of FIG.
From the above results, it was confirmed that the obtained compound was triphenylsiloxytrimethoxysilane.

Reference Example 2 Cyclohexylmethylbis (trimethoxysiloxy) silane In a flask equipped with a stirrer, a refluxer, a dropping funnel, and a thermometer, 87.5 g of 1-trimethoxysiloxy-1-methoxy-1-propene (0. 42 mol) and 0.38 g (0.004 mol) of methanesulfonic acid were charged and heated to 50 ° C. After the internal temperature was stabilized, a solution of 32.1 g (0.2 mol) of cyclohexylmethyldisianol in tetrahydrofuran (30 ml) was added dropwise over 2 hours and stirred at that temperature for 3 hours. The reaction solution was distilled to obtain 45.1 g of a fraction having a boiling point of 101-103 ° C./10 Pa.
A mass spectrum, ¹ H-NMR spectrum, and IR spectrum of the obtained fraction were measured.

<Mass spectrum>
m / z 385, 369, 317, 241, 211, 181
¹ H-NMR spectrum (deuterated chloroform solvent): FIG. 5 shows a chart.
IR spectrum: shown in the chart of FIG.
From the above results, it was confirmed that the obtained compound was cyclohexylmethylbis (trimethoxysiloxy) silane.

[Example 2 ] Triisopropylsiloxytriethoxysilane In a flask equipped with a stirrer, a reflux condenser, a dropping funnel and a thermometer, 218.7 g (1.05 mol) of tetraethoxysilane, ethanol solution 3 of 21% sodium ethoxide 3 .2g (0.01 mol) was charged and heated to 80 ° C. After the internal temperature was stabilized, 174.4 g (1.0 mol) of triisopropylsilanol was added dropwise over 2 hours, followed by stirring at that temperature for 2 hours. The reaction solution was distilled to obtain 310.2 g of a fraction having a boiling point of 110 ° C./0.4 kPa.
A mass spectrum, ¹ H-NMR spectrum, and IR spectrum of the obtained fraction were measured.

<Mass spectrum>
m / z 293,249,221,207,193,163
¹ H-NMR spectrum (deuterated chloroform solvent): FIG. 7 shows a chart.
IR spectrum: shown in the chart of FIG.
From the above results, it was confirmed that the obtained compound was triisopropylsiloxytriethoxysilane.

[Examples 3 and 4 and Comparative Example 1] Use as a glass surface treatment agent 0.1 mol of an organoxysilane compound having a siloxane bond synthesized in the above example was mixed with 13 g of 0.2% acetic acid water and 44 g of ethanol. The glass plate was immersed in the solution added to the solution and stirred for 10 hours for 12 hours, pulled up from the solution, and then dried at 70 ° C. for 2 hours. Water drops were dropped on the glass thus surface-treated, and the contact angle was measured.

  It shows that the water repellency was improved by the treatment with the organoxysilane compound having a siloxane bond of the present invention.

2 is a nuclear magnetic resonance spectrum chart of the compound obtained in Example 1. FIG. 3 is an infrared absorption spectrum chart of the compound obtained in Example 1. FIG. 2 is a nuclear magnetic resonance spectrum chart of the compound obtained in Reference Example 1. FIG. 2 is a chart of an infrared absorption spectrum of the compound obtained in Reference Example 1 . 4 is a chart of nuclear magnetic resonance spectrum of the compound obtained in Reference Example 2 . 4 is an infrared absorption spectrum chart of the compound obtained in Reference Example 2. FIG. 2 is a nuclear magnetic resonance spectrum chart of the compound obtained in Example 2. FIG. 3 is an infrared absorption spectrum chart of the compound obtained in Example 2. FIG.

Claims (5)

The following general formula (1)
_{^{(R 1) n Si {OSi}} (CH 3) m (OR 2) 3-m} 4-n (1)
Wherein R ¹ is the same or different monovalent hydrocarbon group having 1 to 10 carbon atoms, at least one is a branched alkyl group having 3 to 10 carbon atoms, and R ² is 1 having 1 to 10 carbon atoms. Valent hydrocarbon group, m is 0 or 1 , and n is 1, 2 or 3.)
An organoxysilane compound having a siloxane bond represented by The organoxysilane compound having a siloxane bond according to claim 1, wherein the branched alkyl group is selected from an isopropyl group, an isobutyl group, a t-butyl group, and a texyl group. An organoxysilane compound having a siloxane bond represented by the general formula (1) is t-butyldimethylsiloxytrimethoxysilane, t-butyldimethylsiloxytriethoxysilane, triisopropylsiloxytrimethoxysilane, or triisopropylsiloxytriethoxysilane. The organoxysilane compound having a siloxane bond according to claim 1 or 2 . The following general formula (2)
(R ¹ ) _n Si (OH) _4-n (2)
(Wherein R ¹ and n are the same as described above.)
And a silanol compound represented by the following general formula (3)

(Wherein R ² and m are the same as above, R ³ and R ⁴ are hydrogen atoms or monovalent hydrocarbon groups having 1 to 10 carbon atoms, and R ⁵ is a monovalent hydrocarbon group having 1 to 10 carbon atoms. .)
The method for producing an organoxysilane compound having a siloxane bond according to claim 1, wherein the silyl ketene acetal compound represented by formula (1) is reacted in the presence of an acid catalyst. The following general formula (2)
(R ¹ ) _n Si (OH) _4-n (2)
(Wherein R ¹ and n are the same as described above.)
And the following general formula (4)
Si (CH ₃ ) _m (OR ² ) _4-m (4)
(In the formula, R ² and m are the same as above.)
The method for producing an organoxysilane compound having a siloxane bond according to claim 1, wherein the organoxysilane compound represented by formula (1) is reacted in the presence of a catalyst.

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