JPH07126272A - Organosilicon compound and its production - Google Patents

Abstract

PURPOSE:To obtain a compound, as an improving agent for a complex material composed of an inorganic and an organic components, capable of giving the material a flexibility and a hydrophobicity, also useful as a hardening agent and an adhesive, as well as easily synthesized and handled at a low production cost. CONSTITUTION:A compound of formula I (wherein, R<1> is a 1-3C monovalent hydrocarbon; R<2> is a 6-14C divalent hydrocarbon; (m) is 1-3), e.g. a compound of formula II is obtained by reacting a hydrosilane of formula III such as trimethoxysilane, etc., with an acid anhydride compound of formula IV (R<3> is a 4-12C divalent hydrocarbon) such as 1,8-decadienylsuccinyl anhydride, etc., in the presence of a hydrosilylation catalyst (preferably, chloroplatinic acid), preferably at a temperature of 50-100 deg.C. Further, from the view point of cost, etc., it is preferred that a molar ratio of the hydrosilane of the formula III/the acid anhydride of the formula IV is 0.8-1.2.

Description

Detailed Description of the Invention

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a novel acid anhydride group-containing organosilicon compound, which is a modifier for a composite material of an inorganic substance and an organic substance, a treating agent for an inorganic surface, a modifier for an organic resin, and a curing agent. , An organic silicon compound useful as an adhesive, etc., and a method for producing the same.

[0002]

BACKGROUND OF THE INVENTION Alkoxysilanes having an acid anhydride skeleton are used as adhesives because they modify the inorganic surface into acid anhydrides and have excellent reactivity with substances having active hydrogen. It is useful.

However, as a conventional alkoxysilane having an acid anhydride skeleton, for example, a method is known in which silane having butadiene and maleic anhydride are introduced by a Diels-Alder reaction, and butadiene is used in this method. Since the silane that it has is an unstable substance, it is difficult to handle and is expensive, which is extremely disadvantageous in practical use.

The present invention has been made in view of the above circumstances.
An object of the present invention is to provide a novel acid anhydride group-containing silane compound (organosilicon compound) which is easy to synthesize and handle and can be produced at low cost, and a production method thereof.

[0005]

Means and Actions for Solving the Problems As a result of intensive studies for achieving the above object, the present inventor has found that hydrosilane represented by the following general formula (2) and acid represented by the following general formula (3). By hydrosilylation reaction with an anhydride compound, an organosilicon compound represented by the following general formula (1) can be easily synthesized and can be obtained at low cost, and this compound is a composite of an inorganic substance and an organic substance. The present invention has been found to be useful as a material modifier, an inorganic surface treatment agent, an organic resin modifier, a curing agent, an adhesive agent, etc., and has led to the present invention.

[0006]

[Chemical 4] (In the formula, R ¹ is a monovalent hydrocarbon group having 1 to 3 carbon atoms, R ² is a divalent hydrocarbon group having 6 to 14 carbon atoms and R ³ is a divalent hydrocarbon group having 4 to 12 carbon atoms, and m is an integer of 1 to 3. Is shown.)

Therefore, the present invention provides the organosilicon compound represented by the above formula (1), the hydrosilane represented by the above formula (2) and the compound represented by the above formula (3) in the presence of a hydrosilyl catalyst. There is provided a method for producing an organosilicon compound represented by the above formula (1), which comprises reacting.

The present invention will be described in more detail below. The organosilicon compound of the present invention is represented by the following formula (1).

[0009]

[Chemical 5]

Here, R ¹ represents a monovalent hydrocarbon group having 1 to 3 carbon atoms, specifically, an alkyl group such as a methyl group, an ethyl group, an n-propyl group or an alkenyl group such as an isopropenyl group. Is exemplified.

R ² is a divalent hydrocarbon group having 6 to 14 carbon atoms. In this case, if the number of carbon atoms is 5 or less, synthesis and handling are difficult. That is, when a compound of formula (3) described later is obtained, α, ω-dienes, maleic anhydride, and a transition metal compound are used as raw materials and synthesized by a metathesis reaction. It will be possible. Further, when the carbon number is 15 or more, the raw material has a high boiling point, so that it is difficult to purify the raw material, a high-purity material cannot be obtained, and the addition reaction is hindered.

Specific examples of R ² include the following, but are not limited to these.

[0013]

[Chemical 6]

[0014]

[Chemical 7]

Therefore, examples of the compound represented by the above formula (1) include, but are not limited to, the following compounds.

[0016]

[Chemical 8]

[0017]

[Chemical 9]

[0018]

[Chemical 10]

[0019]

[Chemical 11]

[0020]

[Chemical 12]

[0021]

[Chemical 13]

[0022]

[Chemical 14]

[0023]

[Chemical 15]

[0024]

[Chemical 16]

[0025]

[Chemical 17]

[0026]

[Chemical 18]

[0027]

[Chemical 19]

[0028]

[Chemical 20]

[0029]

[Chemical 21]

[0030]

[Chemical formula 22]

[0031]

[Chemical formula 23]

The compound of the above formula (1) is synthesized by reacting a hydrosilane represented by the following formula (2) with an acid anhydride compound represented by the following formula (3) in the presence of a hydrosilyl catalyst. You can

[0033]

[Chemical formula 24]

Here, R ³ in the above formula (3) represents a divalent hydrocarbon group having 4 to 12 carbon atoms, and specific examples include the following, but are not limited thereto. .

[0035]

[Chemical 25]

[0036]

[Chemical formula 26]

In the hydrosilylation reaction of the compounds of the above formulas (2) and (3), a known transition metal compound for hydrosilylation may be used as a catalyst, and particularly platinum, rhodium, palladium and ruthenium-based compounds are used. Those are preferable, and these may be diluted with a solvent such as alcohols, aromatics, hydrocarbons, ketones, and chlorine based before use. The reaction conditions are room temperature of 150 ° C., especially 50 to 10
It is preferably carried out in the range of 0 ° C., and may be carried out in the presence of various solvents.

In this reaction, the molar ratio of hydrosilane / acid anhydride compound is 0.5 to 2.0, especially 0.8 to
From the viewpoint of cost and the like, 1.2 is preferable.

The organosilicon compound of the present invention has a long spacer length between the alkoxysilyl group and the acid anhydride group, so that it can be provided with flexibility.

[0040]

INDUSTRIAL APPLICABILITY The organosilicon compound in the present invention is easy to synthesize and handle by a hydrosilylation reaction and can be produced at low cost. It is a modifier for a composite material of an inorganic substance and an organic substance, a treating agent for an inorganic surface, It is useful as a modifier of resin, a curing agent, an adhesive, etc., and when applied to a composite material, it can impart flexibility, hydrophobicity and the like.

[0041]

EXAMPLES The present invention will now be specifically described with reference to examples, but the present invention is not limited to the following examples.

Example 1 In a 1-liter separable flask equipped with a stirrer, a thermometer, a reflux condenser, and a dropping device, 236 g (1 mol) of 1,8-decadienylsuccinyl anhydride as an acid anhydride was added. And toluene 236g
Was charged and the temperature was raised to 80 ° C.
% Toluene solution 1.95 g was added, and trimethoxysilane 122 g (1 mol) as hydrosilane was added to 80%.
C. to 90.degree. C. was slowly added dropwise to maintain the temperature, and after completion of the addition, the mixture was stirred at 80.degree.
6.5 g (yield 91.2%) was obtained, and as a result of measuring viscosity, specific gravity, refractive index, and non-volatile content, viscosity 49.9 cs, specific gravity 1.068, refractive index 1.4641, non-volatile content 95.6%
Met.

Next, as a result of infrared absorption spectrum analysis, nuclear magnetic resonance spectrum analysis and elemental analysis of the above compound, it was confirmed that the compound had the structure shown below.

[0044]

[Chemical 27]

[0045]

[Chemical 28]

[0046]

[Table 1]

[Example 2] 134 g (1 mol) of methyldiethoxysilane was used in place of trimethoxysilane, and synthesis was carried out in the same manner as in Example 1 except that triphenylsilane was 328 as a light brown transparent liquid. 0.2 g (yield 88.7)
%) Was obtained and the same physical properties as in Example 1 were measured. As a result, the viscosity was 55.5 cs, the specific gravity was 1.016, and the refractive index was 1.462.
6, the nonvolatile content was 97.7%.

Next, the same analysis as in Example 1 was performed on the above compound, and it was confirmed that the compound had the structure shown below.

[0049]

[Chemical 29]

[0050]

[Chemical 30]

[0051]

[Table 2]

[Brief description of drawings]

FIG. 1 is a chart showing an NMR spectrum of an organosilicon compound obtained in Example 1 of the present invention.

FIG. 2 is a chart showing an infrared spectrum of the organosilicon compound obtained in Example 1 of the present invention.

FIG. 3 is a chart showing an NMR spectrum of the organosilicon compound obtained in Example 2 of the present invention.

FIG. 4 is a chart showing an infrared spectrum of the organosilicon compound obtained in Example 2 of the present invention.

Claims (4)

[Claims] 1. An organosilicon compound represented by the following general formula (1): [Chemical 1] (In the formula, R ¹ represents a monovalent hydrocarbon group having 1 to 3 carbon atoms, R ² represents a divalent hydrocarbon group having 6 to 14 carbon atoms, and m represents an integer of 1 to ^3. ) 2. The organosilicon compound according to claim 1, wherein R ² is — (CH ₂ ) ₈ —CH═CH— or — (CH ₂ ) ₇ —CH═CH—CH ₂ —. 3. A hydrosilane represented by the following general formula (2) and an acid anhydride compound represented by the following general formula (3) are reacted in the presence of a hydrosilylation catalyst. 1. A method for producing an organosilicon compound. [Chemical 2] 4. A compound of formula (3) is: The manufacturing method according to claim 3, wherein