JPS6216956B2 - - Google Patents

Description

[Detailed description of the invention]

The present invention relates to a novel method for producing aminosilane compounds. Organosilane compounds are useful substances that mediate the bond between organic and inorganic substances, and various compounds and their uses have been developed in recent years. The present invention makes a valuable contribution to this field. It is generally known that the reaction between acid chlorides and primary amines proceeds very easily and yields amide compounds, but there are no known examples of this reaction being applied to aminoalkyltrialkoxysilanes. . According to the invention, the general formula is up to 3 lower alkyl groups, halogen atoms, x
is 0, 1, 2 or 3, Z is a lower alkyl group), a novel organosilane compound is provided,
The compound has the general formula

An acid chloride having the formula ((R) _o is as above) and an aminoalkyltritriamide represented by the general formula NH ₂ CH ₂ (CH ₂ ) _x Si(OZ) ₃ (x and Z are as above). It is produced by reacting an alkoxysilane in the presence of a tertiary amine. In the compound according to the present invention, -CH ₂
The ( _CH2 ) _x- group is limited to any alkylene group having 1 to 4 carbon atoms, such as methylene, ethylene (dimethylene), trimethylene, tetramethylene, and the like. When the number of carbon atoms is 5 or more, it is not industrially easy to manufacture and difficult to obtain as a raw material. Further, the -OZ group is an alkoxy group that can be hydrolyzed under normal conditions, and Z is preferably an alkyl group having up to about 3 carbon atoms. This is because when the number of carbon atoms becomes too large, the rate of hydrolysis becomes slow. Similarly, the lower alkyl group of the acid chloride preferably has up to 3 carbon atoms. When the number of carbon atoms is 4 or more, it is not industrially easy to manufacture and difficult to obtain as a raw material. In short, the reaction of the present invention essentially involves only -COCl and _-NH2 groups. Therefore, R, Z,
There is no limit to the size of x unless it is particularly large, but it will be limited as described above as an industrial practical problem. Examples of tertiary amines used as hydrogen chloride scavengers in the synthesis of organosilanes according to the invention are triethylamine, tripropylamine, tributylamine, pyridine, N.N-dimethylaniline, and the like. The reaction is usually carried out in a solvent inert towards acid chlorides, aminoalkyltrialkoxysilanes and tertiary amines, such as ethyl ether, benzene, n-hexane, toluene, tetrahydrofuran.
It is carried out at a temperature below the boiling point of these solvents. The reaction proceeds with the formation of the desired product, namely RCONHCH ₂ (CH ₂ ) _x Si(OZ) ₃ and the precipitation of a by-product, namely tertiary amine hydrochloride. and get the object. The aminoalkyltrialkoxysilane reactant reacts acrylonitrile with trichlorosilane using tri-n-butylamine as a catalyst;
The resulting chlorosilane adduct is alkoxylated,
It can then be synthesized by hydrogenating the nitrile group. An advantageous feature of the organosilane obtained according to the invention is that it has at one end of its molecule a functional group having an amide bond, and at the other end a functional group that generates a siloxane bond by hydrolysis, - CH ₂
The (CH ₂ ) _x - group provides a stable bridge that connects a functional group containing an amide bond to this silicon atom. The organosilanes obtained in accordance with the present invention are useful in providing superior strength and weather resistance to molded articles formed from organic resin materials and inorganic base components or aggregates, thus providing superior molded articles. can be manufactured. Examples of the present invention will be described below, but these examples are merely illustrative of the present invention and are not intended to limit it in any way. Example 1 Equipped with stirrer, condenser, and dropping funnel
In a 250 ml reaction vessel, add 44 g of γ-aminopropyltriethoxysilane and 20 g of triethylamine.
Add 100 ml of ethyl ether and dropwise add 28 g of benzoyl chloride while stirring under nitrogen atmosphere. The reaction vessel was cooled with ice water since the reaction occurred violently. After the dropwise addition was completed, the reaction was stirred at 20° C. for 1 hour. Next, the precipitate was separated, washed with ethyl ether, the ethyl ether in the liquid was distilled off, and then the reaction product was collected by distillation under reduced pressure. The product had a boiling point of 190-195°C/4 mmHg and a yield of 55 g, 83%. The product was determined by infrared absorption spectroscopy (IR) and nuclear magnetic resonance spectroscopy (NMR) to identify phenyl groups, amide groups, Si-O-C bonds, _-CH2 - _CH2 - _CH2 -bonds,
(See Figures 1 and 2) was identified. Example 2 In the same apparatus as in Example 1, 44 g of γ-aminopropyltriethoxysilane and 16 g of pyridine were added.
100 ml of benzene is charged and 31 g of m-methylbenzoyl chloride is added dropwise while stirring in a nitrogen atmosphere. After the addition was completed, the reaction was stirred at 20° C. for 1 hour. Next, the precipitate was separated, and after washing with ethyl ether, the ether and benzene in the liquid were distilled off, and 68 g of the reaction product was obtained, with a yield of 100.
It was %. The product was prepared in the same manner as in Example 1. was identified. That is, the m-CH ₃ group of the phenyl group is
Confirmed by comparison of nuclear magnetic resonance spectra with the starting acid chloride. Similarly, derivatives of O-methylbenzoyl chloride and p-methylbenzoyl chloride were obtained in yields of 67 g and 68 g, 99% and 100%, respectively, and were similarly identified. Example 3 Into the same apparatus as in Example 1, 44 g of γ-aminopropyltriethoxysilane, 20 g of triethylamine, and 100 ml of n-hexane were placed, and while stirring in a nitrogen atmosphere, 35 g of p-chlorochloride was added. Add benzoyl dropwise. Hereinafter, the same operations as in Example 2 were performed. And 70.5g of reaction product was obtained,
The yield was 98%. The product was prepared in the same manner as in Example 2. was identified. Similarly, O-chlorobenzoyl chloride and m-chloride
Regarding chlorobenzoyl, derivatives thereof were obtained in yields of 70 g and 71 g, 97% and 99%, respectively, and were similarly identified.

[Brief explanation of the drawing]

FIG. 1 is a chart of infrared spectroscopic analysis of a compound obtained by the production method of the present invention. Figure 2 is a chart of nuclear magnetic resonance analysis of the same compound.

Claims (1)

[Claims] 1. General formula represented by the _{formula NH 2} CH ₂ (CH _{2 )} Z is a lower alkyl group, x is 0, 1, 2 or 3
An aminoalkyltrialkoxysilane that is
General formula consisting of reaction in the presence of a tertiary amine A method for producing a novel organosilane compound represented by the formula, where Z and x are the same as described above.