Curable polyvinyl benzyl compound and process for producing the same

Abstract

A curable polyvinyl benzyl compound represented by the following general formula (1) wherein R1 represents a C2-20 organic group, R2 represents a hydrogen atom, etc., x is an integer of 0 to 4, and n is an integer of 0 to 2. The compound is obtained by reacting a fluorene compound with a vinylbenzyl halide in the presence of an alkali.

Description

CROSS REFERENCE TO RELATED APPLICATIONS [0001] This application is a Divisional of U.S. application Ser. No. 10 / 954,214 filed Oct. 1, 2004, which is a Continuation-In-Part of U.S. application Ser. No. 10 / 474,453 filed Oct. 8, 2003, which is the National Stage of PCT / JP02 / 02851 filed on Mar. 25, 2002.TECHNICAL FIELD [0002] The present invention relates to a compound which provides a cured product having high heat resistance, low water absorption and excellent dielectric properties which are required for organic insulating materials for use in electronic equipment such as communication equipment and to a process for producing the same. More specifically, the present invention relates to a curable polyvinyl benzyl compound obtained by reacting a fluorene compound with a vinylbenzyl halide, a process for producing the same, and a curable resin composition and a cured resin obtained by using the same. Further, the present invention relates to a substrate, a prepreg and a metal foil havin...

AI Technical Summary

Benefits of technology

[0065] Since a highly polymerizable unsaturated halide such as vinylbenzyl halide is used in the present invention, a thermal polymerization inhibitor may be optionally added to the reaction system. Examples thereof include t-butylcatechol, 2,4-di-t-butylphenol, 2-t-butylphenol, 2-t-butyl-4-nitrophenol, 2,4-dinitrophenol, hydroquinone, methyl hydroquinone, hydroquinone monomethyl ether, t-butylhydroquinone, resorcin, pyrogallol, phenothiazine or copper salt. Further, use of a suitable amount of air is effective in inhibiting polymerization.

[0080] In the present invention, to impregnate the curable resin composition with the fiber material, either a known solvent method or a solvent-free method may be used. As for the solvent to be used in the solvent method, a solvent having a relatively low boiling point such as a ketone-based solvent exemplified by acetone, methyl ethyl ketone and methyl isobutyl ketone, or an aromatic hydrocarbon-based solvent exemplified by benzene and toluene may be used in order to reduce the amount of the residual solvent contained in the prepreg as much as possible and avoid a reduction in heat resistance, cracking or the formation of voids.

[0095] Examples of the indene compound used in the present invention include an indene compound whose indene and aromatic ring parts thereof may be substituted with a halogen atom, an alkyl group, alkoxy group, or thioalkoxy group each having 1 to 5 carbon atoms, or an aryl group as represented by the above general formula 5. The indene compound may be used alone or in combination of two or more compounds. The substituted indene compound may be synthesized easily by halogenating an aromatic part of indene with bromine or the like and introducing a desired group into the halogenated part.

[0108] A curable resin composition of the present invention is prepared by mixing a curable vinylbenzyl compound with a compound copolymerizable with the curable vinylbenzyl compound for improved moldability and for other purposes.

[0122] A known solvent process or a solvent-free process may be used to impregnate the fiber material with the curable vinylbenzyl compound or curable resin composition. The solvent used in the solvent process is a solvent having a relatively low boiling point for minimizing the amount of the residual solvent in the prepreg and avoiding reduction in heat resistance and formation of cracking or voids. Examples of the solvent used in the solvent process include: a ketone-based solvent such as acetone, methyl ethyl ketone, or methyl isobutyl ketone; and an aromatic hydrocarbon-based solvent such as benzene or toluene.

[0172] A known solvent process or a solvent-free process may be used to impregnate the fiber material with the polymerizable composition. The solvent used in the solvent process is a solvent having a relatively low boiling point for minimizing the amount of the residual solvent in the prepreg and avoiding reduction in heat resistance and formation of cracking or voids. Examples of the solvent used in the solvent process include: a ketone-based solvent such as acetone, methyl ethyl ketone, or methyl isobutyl ketone; and an aromatic hydrocarbon-based solvent such as benzene or toluene.

Problems solved by technology

However, the above materials proposed in the prior art have various problems such as a low crosslinking density and a large linear expansion coefficient; low chemical resistance; poor tenacity; a large number of complicated steps required for the production of a resin from raw materials; and the need for a special solvent for shaping.

Therefore, they have not been put to practical use yet.

However, the requirements for dielectric properties of electronic materials are becoming more and more demanding.

Next-generation communication devices have begun to appear, which require, in particular, a low dielectric dissipation factor, which cannot be satisfied even by the above vinylbenzyl ether compound.

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