Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – From silicon reactant having at least one...
Reexamination Certificate
2001-03-07
2003-01-14
Dawson, Robert (Department: 1712)
Synthetic resins or natural rubbers -- part of the class 520 ser
Synthetic resins
From silicon reactant having at least one...
C528S034000, C528S103000, C528S104000, C528S106000, C528S310000, C528S367000, C525S393000, C525S396000, C525S407000, C525S452000, C525S540000, C556S444000, C556S467000, C556S478000
Reexamination Certificate
active
06506868
ABSTRACT:
CROSS-REFERENCE TO RELATED APPLICATIONS
This application is a national phase application of International Application No. PCT/JP00/04737, which was filed on Jul. 14, 2000 and which published in Japanese on Jan. 25, 2001, which in turn claims priority from Japanese Application No. 11/201446, which was filed on Jul. 15, 1999, Japanese Application No. 11/225959, which was filed on Aug. 10, 1999, Japanese Application No. 2000/55552, which was filed on Mar. 1, 2000, Japanese Application No. 2000/108631, which was filed on Apr. 10, 2000, and Japanese Application No. 2000/115588, which was filed on Apr. 17, 2000.
1. Technical Field
The present invention relates to a partial condensate of glycidyl ether group-containing alkoxysilane, a silane-modified resin, compositions thereof and preparation methods thereof.
2. Background Art
In recent years, there is an increasing demand for high-performance cured products of epoxy resin in the field of electric and electronic materials. In particular, the products having higher heat resistance are required.
In order to improve the heat resistance of the cured products of epoxy resin, glass fibers, glass particles, mica and like fillers are added to epoxy resins and curing agents. However, these methods using fillers can not sufficiently improve heat resistance of the cured products of epoxy resin. By these methods, the transparency of the resulting cured products is deteriorated and the interfacial adhesion between the fillers and the epoxy resin is lowered. Thus, the cured products are given insufficient mechanical properties.
Another method for improving the heat resistance of the epoxy resin cured product is to subjecting the epoxy resin to the reaction with a silane coupling agent. However, employment of the silane coupling agent often lowers the glass transition temperature (Tg) of the resin. In addition, the silane coupling agents are usually expensive and not very favorable in terms of the cost.
Japanese Unexamined Patent Publication No. 1996-100107 proposes a method for improving the heat resistance of cured products of epoxy resin compositions by using the complex of an epoxy resin and silica. The complex of an epoxy resin and silica is prepared by adding hydrolyzable alkoxysilane to a solution of a partially cured epoxy resin to further cure the partially cured product; hydrolyzing the alkoxysilane to cause solation; and polycondensing the sol to cause gelation. The heat resistance of the cured product prepared from such complex is improved to some extent compared to the cured product of the epoxy resin by itself. However, water contained in the complex or water and alcohols produced during curing cause voids (air bubbles) inside the cured product. Further, increasing the amount of alkoxysilane to further improve the heat resistance of the cured product results in impaired transparency and whitening of the cured product due to the aggregation of silica produced by sol-gel curing reaction. In addition, solation of a large amount of the alkoxysilane necessitates a large amount of water, which leads to bends and cracks in the cured product.
Meanwhile, there has been reported many studies on silica complexation of various high molecular compounds other than the epoxy resin, in order to improve their heat resistance, toughness, gas barrier properties and the like, by sol-gel curing reaction of hydrolyzable alkoxysilane (Japanese Unexamined Patent Publications No. 1999-92623, No. 1994-192454, No. 1998-168386, No. 1998-152646, No. 1995-118543, etc.). However, in the complex produced by the sol-gel curing reaction, silica is dispersed within the resin by using the hydrogen bonds between the silanol groups produced by hydrolysis of the hydrolyzable alkoxysilane and hydrogen bonding functional groups in a high molecular compound. Therefore, this reaction can not be employed for the high molecular compounds which have no hydrogen bonding functional groups or the high molecular compounds having high Tg, which tend to aggregate.
DISCLOSURE OF INVENTION
An object of the present invention is to provide a novel partial condensate of glycidyl ether group-containing alkoxysilane, compositions thereof and preparation methods thereof, the partial condensate being capable of improving the heat resistance and other properties of a cured product by adding to or modifying a resin such as epoxy resin, polyimide resin, polyamide-imide resin, phenol resin and the like.
Another object of the present invention is to provide a silane-modified resin modified with the above partial condensate of glycidyl ether group-containing alkoxysilane, a resin composition thereof and preparation methods thereof.
Other objects and features of the present invention are described below.
The present invention provides a partial condensate of glycidyl ether group-containing alkoxysilane which is obtainable by dealcoholization reaction between glycidol and a partial condensate of alkoxysilane, and preparation methods thereof.
Further, the present invention provides a composition comprising the above partial condensate of glycidyl ether group-containing alkoxysilane.
Further, the present invention provides an alkoxy-containing silane-modified polyimide resin which is prepared by subjecting a polyamic acid and the above partial condensate of glycidyl ether group-containing alkoxysilane to epoxy ring-opening esterification, dehydration and cyclization, and preparation methods thereof.
Further, the present invention provides an alkoxy-containing silane-modified polyamide-imide resin which is prepared by subjecting a polyamide-imide resin having a carboxyl group and/or an acid anhydride group at the end(s) of its molecule and the above partial condensate of glycidyl ether group-containing alkoxysilane to epoxy ring-opening esterification, and preparation methods thereof.
Further, the present invention provides a composition comprising the above silane-modified polyamide-imide resin.
Further, the present invention provides an alkoxy-containing silane-modified phenol resin which is prepared by subjecting a phenol resin and the above partial condensate of glycidyl ether group-containing alkoxysilane to epoxy ring-opening reaction, and preparation methods thereof.
Furthermore, the present invention provides a composition comprising the above silane-modified phenol resin.
The inventors of the present invention conducted extensive research to solve the above-mentioned problems of the prior art. Accordingly, the inventors found the following. According to a resin composition which comprises the above specific partial condensate of glycidyl ether group-containing alkoxysilane and an epoxy resin, or a silane-modified resin, which is a high molecular compound such as polyimide resin, polyamide-imide resin, phenol resin or the like modified with the condensate, it is possible to provide a resin silica hybrid which is a cured product having improved heat resistance and mechanical strength and being free from voids, cracks and the like. The present invention was accomplished based on these findings.
Partial Condensate of Glycidyl Ether Group-containing Alkoxysilane
The partial condensate of glycidyl ether group-containing alkoxysilane of the present invention is prepared by dealcoholization reaction between glycidol and the partial condensate of alkoxysilane.
The resulting partial condensate of glycidyl ether group-containing alkoxysilane is typically represented by the following formula (1).
Formula
wherein R
1
represents a glycidyl ether group, a C
1
-C
3
alkoxy group or a group represented by the formula
[in this formula, R
3
represents a glycidyl ether group, a C
1
-C
3
alkoxy group or a group represented by the formula
(in this formula, R
5
represents a glycidyl ether group or a C
1
-C
3
alkoxy group, R
6
represents a C
1
-C
8
alkyl group or aryl group, a glycidyl ether group or a C
1
-C
3
alkoxy group), R
4
represents a C
1
-C
8
alkyl group or aryl group, a glycidyl ether group, a C
1
-C
3
alkoxy group or a group represented by the above formula (3)], R
2
represents a C
Goda Hideki
Higashino Tetsuji
Takeda Shoji
Arakawa Chemical Industries Ltd.
Baker & Botts L.L.P.
Dawson Robert
Robertson Jeffrey B.
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