JP3268399B2 - New organosilicon compounds - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a novel organosilicon compound which has not been disclosed in the literature, and more particularly to an organosilicon compound which is useful as an electron-donating compound in producing an α-olefin polymer in a magnesium chloride-supported Ziegler-Natta catalyst system. (Texyl (tert-butoxy) dimethoxysilane). This silane compound can also be used as a silane coupling agent or a resin modifier.

[0002]

2. Description of the Related Art Supported Zieg for α-olefin polymer production
It is well known that the use of an organosilicon compound as an electron-donating compound of the ler-Natta catalyst system, for example, a trialkoxysilane compound such as phenyltriethoxysilane, improves the stereoregularity of the produced polymer. Is
(For example, JP-A-57-63310, JP-A-57-63311, JP-A-2-
17803, JP-A-2-229807 and JP-A-4-26693). However,
Conventionally used trialkoxysilane compounds are not economically disadvantageous for industrial use because they significantly deactivate the catalytic activity, and the stereoregularity of the α-olefin polymer obtained is not necessarily the same as that of the present. It did not satisfy the request. In addition, silane compounds are expected to be used as silane coupling agents or resin modifiers, and therefore, the appearance of new silane compounds has long been desired.

[0003]

The problem to be solved by the present invention is that α-
A novel organosilicon compound that is useful as an electron-donating compound for magnesium chloride-supported Ziegler-Natta catalysts, a catalyst for the production of olefin polymers, and can also be used as a silane coupling agent or resin modifier It is to be.

[0004]

DISCLOSURE OF THE INVENTION The present inventors have developed a magnesium chloride-supporting Ziegler-Natt for producing an α-olefin polymer.
a As a result of various studies to develop a new electron-donating compound useful for the catalyst system, the chemical formula, HC (CH ₃ ) ₂ C (CH ₃ ) ₂ -Si (OCH ₃ ) ₂ (OC (CH ₃ ) ₃ ) Is capable of producing an α-olefin polymer having high stereoregularity without lowering the polymerization activity as compared with a conventionally known electron donating compound. And completed the present invention. The above effect is obtained when the carbon atom at the β-position (second from the silicon atom) of the silicon atom is an alkyl substituent of a secondary carbon and one of the alkoxy substituents is te.
The effect was first manifested by making the rt-butyl group and the remaining two alkoxy substituents methoxy groups. The novel silane compound can be used as a silane coupling agent or a resin modifier.

This texyl (tert-butoxy) dimethoxysilane is represented by the chemical formula: HC (CH ₃ ) ₂ C (CH ₃ ) ₂ -Si (OCH ₃ ) ₂ (OC (CH ₃ ) ₃ ). An organosilicon compound is prepared by reacting texyltrihalosilane with tert-butyl alcohol, and then reacting the resulting reactant (texil (texyl)
(rt-butoxy-dihalosilane) and methanol.

Hereinafter, the manufacturing method will be described in detail. First, as shown in the following formula (1), texil trihalosilane is reacted with tert-butyl alcohol to produce texyl (tert-butoxy) dimethoxysilane. At this time, it is particularly preferable to coexist a dehydrohalogenating agent in the reaction system.

Embedded image However, in the formula (1), X represents a halogen atom,
Among them, Cl or Br is preferred. Examples of the dehydrohalogenating agent include urea, tertiary amines, nitrogen-containing polycyclic compounds such as pyridine, quinoline and isoquinoline, among which urea, pyridine and quinoline are preferably used. When performing the reaction represented by the above formula (1), texyltrihalosilane 1
Per mole, tert-butyl alcohol is used in an amount of 1 to 10 moles, and the dehydrohalogenating agent is used in an amount of 1 to 10 moles, and 0 to 150 ° C, preferably 30 to 80 ° C. It is desirable to react for 20 hours, preferably 2 to 10 hours.

Then, texyl (tert-butyl) dihalosilane obtained by the reaction represented by the above formula (1) is reacted with methanol as shown by the following formula (2).
Texyl (tert-butoxy) dimethoxysilane according to the invention is obtained.

Embedded image

In order to produce the novel mixed alkoxyl group-containing organosilicon compound of the present invention, an alcohol exchange reaction between texyltrimethoxysilane and tert-butyl alcohol can be used. In the alcohol exchange reaction, a generally known acid or base can be used as a catalyst.

The thus obtained texil (tert-
Butoxy) dimethoxysilane includes: mass spectrometry by gas chromatography (EI method) m / e: 248 (M +) 1H-NMR analysis value measured using deuterated chloroform as a solvent
· Figure ^{1 δ (1 H / ppm)} : 0.889 (m, 12H), 1.306 (s, 9H), 1.736 (d,
2H), 1.575 (m, 1H), 3.550 (s, 6H) ^13C -NMR measured using deuterated chloroform as a solvent
Figure 2 δ ( ¹³ C / ppm): 18.3, 21.1, 25.4, 31.5, 34.5, 50.
Texyl (tert-butoxy) represented by the chemical formula: HC (CH ₃ ) ₂ C (CH ₃ ) ₂ -Si (OCH ₃ ) ₂ (OC (CH ₃ ) ₃ ) It could be confirmed that it was dimethoxysilane.

[0010]

Next, examples of the present invention will be described. (Example 1) 2 equipped with a magnetic stirrer, a cooling tube, and a dropping funnel
Texyltrichlorosilane 2 in a 00 ml three-necked flask
1.9 g (100 mmol), urea 27.0 g (450
Mmol) and 100 ml of dry ether, and the flask was cooled with ice water. 8.6 g (100 mmol) of tert-butyl alcohol and 20 parts of dry ether
ml of the mixed solution was added dropwise over 30 minutes. Thereafter, the mixture was heated under reflux for 3 hours. The flask was again cooled with ice water, 6.4 g (200 mmol) of methanol and 30 m of dry ether.
1 was added dropwise over 20 minutes. After the completion of the dropwise addition, the reaction was completed by heating under reflux for 20 hours. The ether layer was concentrated by a rotary evaporator and distilled under reduced pressure to obtain 16.1 g of texyl (tert-butoxy) dimethoxysilane.
(65 mmol). Yield 65%, boiling point 78 ~
It was 80 degrees / 9 mmHg. The structure is GC-MS, ¹
Confirmed by 1 H-NMR and ¹³ C-NMR. ¹ H-NMR,
The charts of ¹³ C-NMR are shown in FIGS. 1 and 2, respectively.

Example 2 10 g (49 mmol) of texyltrimethoxysilane, 2.9 g (49 mmol) of tert-butyl alcohol, and potassium t
30 mg (0.3 mmol) of tert-butoxide were charged and heated for 24 hours. After cooling, neutralize the alkali,
Distillation under reduced pressure gives texil (tert-butoxy)
6.2 g (25 mmol) of dimethoxysilane were obtained. The yield was 51%.

[0012]

The novel texyl (tert-butoxy) dimethoxysilane of the present invention is a magnesium chloride-supported Zi
It is useful as an electron-donating compound when producing an α-olefin polymer in an egler-Natta catalyst system. This silane compound can also be used as a silane coupling agent or a resin modifier.

[Brief description of the drawings]

FIG. 1 is a ¹ H-NMR spectrum of texyl (tert-butoxy) dimethoxysilane of the present description.

FIG. 2 is a ¹³ C-NMR spectrum of texyl (tert-butoxy) dimethoxysilane of the present description.

──────────────────────────────────────────────────の Continued on the front page (58) Field surveyed (Int. Cl. ⁷ , DB name) C07F 7/18 C07F 7/02 CA (STN) REGISTRY (STN)

Claims (1)

(57) [Claims] 1. Texyl (tert-butoxy) dimethoxysilane represented by the chemical formula HC (CH ₃ ) ₂ C (CH ₃ ) ₂ -Si (OCH ₃ ) ₂ (OC (CH ₃ ) ₃ ).