Preparation of bis(3-aminopropyldimethylsilyl)benzene compounds

Details Preparation of bis(3-aminopropyldimethylsilyl)benzene compounds Preparation of bis(3-aminopropyldimethylsilyl)benzene compounds

1999-05-10

2001-08-14

Shaver, Paul F. (Department: 1621)

Organic compounds -- part of the class 532-570 series

Organic compounds

Silicon containing

Reexamination Certificate

active

06274754

ABSTRACT:

This invention relates to a novel process for preparing bis(3-aminopropyldimethylsilyl)benzene compounds which are useful as a modifier for polyimides for use in semiconductor isolation films and liquid crystal alignment layers or a modifier for polyamides, polyurethane, etc.
BACKGROUND OF THE INVENTION
Bis(3-aminopropyldimethylsilyl)benzene compounds are useful as a modifier for polyimides for use in semiconductor isolation films, semiconductor manufacturing photosensitive resins, and liquid crystal alignment layers for improving adhesion and moldability thereof or a modifier for polyamides, polyurethane, etc. for tailoring properties thereof.
Several processes are known for preparing bis(3-aminopropyldimethylsilyl)benzene compounds. One known process for producing 1,4-bis(3-aminopropyldimethylsilyl)-benzene is by effecting direct hydrosilylation reaction between allylamine and 1,4-bis(dimethylsilyl)benzene in the presence of a platinum catalyst (Izv. Akad. Nauk SSSR Ser. Khim., 2249 (1969)). Another process is effecting hydrosilylation reaction between N-(trimethylsilyl)-allylamine and 1,4-bis(dimethylsilyl)benzene in the presence of a platinum catalyst, followed by detrimethylsilylation reaction (Dokl. Akad. Nauk SSSR, 179, 600 (1968)).
However, the former process is low in yields and difficult to produce the end compound of high purity because the reaction is not only very slow and time consuming, but also entails many side reactions. The latter process has the drawback that the starting reactant, N-(trimethylsilyl)allylamine is difficult to handle because it is so reactive that it is likely to decompose with humidity in air. There is available no commercial process for preparing N-(trimethylsilyl)-allylamine.
In addition, either of these processes has the problem that hydrosilylation reaction entails large amounts of isomers in which addition takes place internally rather than at terminals, resulting in the end compound having admixed therein (2-aminopropyldimethylsilyl)(3-aminopropyldimethylsilyl)benzene. This isomer is heat unstable as compared with the end compound. When the product having the isomer admixed therein is used in the polyimide-modifying application where heat resistance is important, the performance of the product is unsatisfactory.
SUMMARY OF THE INVENTION
Therefore, an object of the invention is to provide a novel and improved process for preparing a bis(3-amino-propyldimethylsilyl)benzene compound in a simple and inexpensive manner and in high yields without forming isomers.
We have found that by effecting hydrosilylation reaction between N,N-bis(trimethylsilyl)allylamine and a bis(dimethylsilyl)benzene compound in the presence of a platinum catalyst, then effecting detrimethylsilylation reaction, a bis(3-aminopropyldimethylsilyl)benzene compound can be synthesized in high yields without forming isomers. The process is simple and inexpensive to synthesize the end compound.


REFERENCES:
patent: 4927953 (1990-05-01), Takatsuna et al.
patent: 5047526 (1991-09-01), Yamamoto
patent: 5227504 (1993-07-01), Shinohara et al.
Izv. Akad Nauk SSSR Ser. Khim., 2449 (1969).
Dokl. Akad Nauk SSSR, 179, 600 (1968).

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