JP3122347B2 - Organosilicon compound and method for producing the same - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an organosilicon compound used as a raw material for polysiloxane or polysilane, and a method for producing the same.

[0002]

2. Description of the Related Art Bis (monochlorosilyl) group-containing compounds having two monochlorosilyl groups in the molecule are known as raw materials for polysiloxane or polysilane.
Examples of such a bis (monochlorosilyl) group-containing compound include 1,4-bis (chlorodimethylsilyl) benzene and 1,2-bis (chlorodimethylsilyl) ethane. 1,4-bis (chlorodimethylsilyl) benzene has extremely low flexibility, and 1,2-bis (chlorodimethylsilyl) ethane has extremely high flexibility. Polysiloxanes and polysilanes obtained from both with extreme flexibility exhibit extreme properties. Therefore, it is desired to develop a bis (monochlorosilyl) group-containing compound having appropriate flexibility and to easily produce polysiloxane and polysilane having excellent properties from the bis (monochlorosilyl) group-containing compound. I have.

[0003]

DISCLOSURE OF THE INVENTION The present invention has been made to solve the above-mentioned problems, and a novel organosilicon compound containing a bis (monochlorosilyl) group and having a suitable flexibility. It is an object of the present invention to provide a manufacturing method thereof.

[0004]

Means for Solving the Problems As a result of extensive studies, the present inventors have found that an organosilicon compound having a monochlorosilyl group bonded to a benzene ring and a monochlorosilyl group bonded to an alkyl group in a molecule. The present inventors have found that polysiloxanes and polysilanes having excellent characteristics can be easily produced, and the present invention has been completed.

That is, the organosilicon compound of the present invention has the following formula [I]

[0006]

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[0007] R ^{1 to} R ⁴ in the formula may be the same or different hydrocarbon groups having 1 to 10 carbon atoms, and it is particularly preferable that all are methyl groups. The hydrocarbon group is specifically an alkyl group, a cycloalkyl group, or an aryl group. Examples of the alkyl group include a methyl group, an ethyl group, and an isobutyl group. Examples of the cycloalkyl group include a cyclopentyl group and a cyclohexyl group. Examples of the aryl group include a phenyl group and a naphthyl group.

The organosilicon compound represented by the formula (I) is
It is a bis (monochlorosilyl) group-containing compound obtained by reacting a styrene compound having a hydrogensilane group with a dichlorosilane compound in the presence of aluminum chloride as shown in the following reaction formula.

[0009]

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Styrene compounds having a hydrogensilane group include, for example, (4-vinylphenyl) dimethylsilane, (4-vinylphenyl) diethylsilane,
(Vinylphenyl) isobutylmethylsilane, (4-vinylphenyl) cyclohexylmethylsilane, and (4-vinylphenyl) methylphenylsilane.

Examples of the dichlorosilane compound include dimethyldichlorosilane, diethyldichlorosilane, n-propylmethyldichlorosilane, cyclohexylmethyldichlorosilane, and methylphenyldichlorosilane. These compounds are preferably used in an amount of 0.1 to 10 mol%, particularly 0.5 to 5 mol%, based on the styrene compound having a hydrogensilane group.

The reaction is preferably carried out at 0 to 50 ° C. During the reaction, a solvent inert to aluminum chloride may be added. Examples of the solvent include toluene, n-hexane, and cyclohexane. After the reaction is completed, it is preferable to add a Lewis base such as an ether compound to inactivate the aluminum chloride in order to prevent a side reaction due to distillation with aluminum chloride.

The compound containing a bis (monochlorosilyl) group obtained by the above reaction formula is chlorodialkylsilyl-
(2-chlorodialkylsilyl) ethylbenzene, specifically, 1-chlorodimethylsilyl-4- (2-
Chlorodimethylsilyl) ethylbenzene, 1-chlorodiethylsilyl-4- (2-chlorodimethylsilyl) ethylbenzene, 1-chloromethylisobutylsilyl-4-
(2-chlorodimethylsilyl) ethylbenzene, 1-chlorocyclohexylmethylsilyl-4- (2-chlorodimethylsilyl) ethylbenzene, 1-chloromethylphenylsilyl-4- (2-chlorodimethylsilyl) ethylbenzene, 1-chlorodimethylsilyl -4- (2-chlorodiethylsilyl) ethylbenzene, 1-chlorodimethylsilyl-4- (2-chloromethyl-n-propylsilyl) ethylbenzene, 1-chlorodimethylsilyl-4-
(2-chloromethylphenylsilyl) ethylbenzene,
Examples thereof include 1-chlorodiethylsilyl-4- (2-chlorodiethylsilyl) ethylbenzene and 1-chloromethylphenylsilyl-4- (2-chloromethylphenylsilyl) ethylbenzene.

[0014]

As described above, polysiloxane and polysilane having excellent properties can be easily synthesized from the organosilicon compound of the present invention as a raw material.

[0015]

Embodiments of the present invention will be described below in detail.

Example 1 Dimethyldichlorosilane was placed in a 500 ml flask equipped with a stirrer, reflux condenser, thermometer and dropping funnel.
6 g (0.4 mol) and 0.27 g (0.2 mmol) of aluminum chloride as a catalyst were charged. 32.5 g of (4-vinylphenyl) dimethylsilane from the dropping funnel
(0.2 mol) was added dropwise at 15 to 20 ° C. over 2 hours,
A reaction solution was obtained. After 0.4 g of anisole was added to the reaction solution to deactivate aluminum chloride, the reaction mixture was distilled to obtain 113-113.
47.2 g of a 115 ° C./1.5 mmHg fraction was collected.

The mass spectrum, nuclear magnetic resonance spectrum (NMR) and infrared absorption spectrum of the obtained compound were measured.

The measurement results of the mass spectrum are as shown below.

Mass spectrum (EI method): m / z (assignment) 290, 292, 294 (molecular ion (M ⁺ ) peak) ¹ H and ¹³ C nuclear magnetic resonance spectra were measured using chloroform as a solvent. Was. The measurement results are as shown in Table 1. Table 1 shows ¹ H of the new silane compound,
The position of the ¹³ C chemical shift is shown.

[0020]

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[0021]

[Table 1]

The measurement results of the infrared absorption spectrum (IR) are shown in FIG. 1 as a spectrum chart.

From these results, the obtained compound was 1-
It was confirmed to be chlorodimethylsilyl-4- (2-chlorodimethylsilyl) ethylbenzene. Yield 8
1%.

Example 2 Dimethyldichlorosilane and (4-vinylphenyl) dimethylsilane were reacted in the same manner as in Example 1 except that 100 ml of toluene was used as a solvent. 0.4 g of anisole was added to the obtained reaction solution to deactivate the aluminum chloride catalyst.
When a fraction of 1.5 mmHg was collected, 49.5 g of 1-chlorodimethylsilyl-4- (2-chlorodimethylsilyl) ethylbenzene was obtained. The yield was 85%.

[Brief description of the drawings]

FIG. 1 is a diagram showing an infrared absorption spectrum of an organosilicon compound to which the present invention is applied.

────────────────────────────────────────────────── ─── Continuing from the front page (72) Inventor Tomiaki Hirahara 28-1, Nishifukushima, Oku-ku, Nikushiro-gun, Niigata Prefecture Shinsei Chemical Industry Co., Ltd. Synthetic Technology Research Institute (56) References JP-A-3-294282 (JP, A) JP-A-3-14590 (JP, A) JP-A-59-157089 (JP, A) (58) Fields investigated (Int. Cl. ⁷ , DB name) C07F 7/12 C08G 77 / 42 CA (STN) CAOLD (STN) REGISTRY (STN) WPIDS (STN)

Claims (3)

(57) [Claims] [Claim 1] The following formula [I] Wherein R ^{1 to} R ⁴ are the same or different and have 1 to 10 carbon atoms.
An organosilicon compound represented by the formula: 2. The organosilicon compound according to claim 1, wherein all of R ^{1 to} R ⁴ are methyl groups. 3. The following formula [II] (Wherein R ^{1 and} R ² are the same or different and have 1 to 10 carbon atoms)
A styrene compound having a hydrogen silane group represented by the following formula [III]: (In the formula, R ^{3 to} R ⁴ are the same or different and have 1 to 10 carbon atoms.
A method for producing chlorodialkylsilyl- (2-chlorodialkylsilyl) ethylbenzene, which comprises reacting a dichlorosilane compound represented by the formula (I) with a dichlorosilane compound represented by the formula: