Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – From phenol – phenol ether – or inorganic phenolate
Reexamination Certificate
2001-10-16
2003-04-15
Dawson, Robert (Department: 1712)
Synthetic resins or natural rubbers -- part of the class 520 ser
Synthetic resins
From phenol, phenol ether, or inorganic phenolate
C528S094000, C528S112000, C549S517000, C549S522000, C549S541000, C549S542000, C549S544000
Reexamination Certificate
active
06548620
ABSTRACT:
TECHNICAL FIELD OF THE INVENTION
The present invention relates to a tetramethylbiphenyl type high performance epoxy resin composition useful in electrical and electronic fields and the like, a process for producing the high performance epoxy resin composition, and a curable epoxy resin composition using the high performance epoxy resin composition.
PRIOR ART
Because of their excellent curing properties and ease of handling, epoxy resins are used in wide fields of adhesion, casting, encapsulation, lamination, molding, coating, and the like.
In general, epoxy resins which have been industrially produced and used have a molecular weight distribution in their main component itself, and are mixtures (compositions) of many components containing various impurities. The majority of these impurities are brought in from raw materials of the epoxy resin, or produced by side-reactions or the like in the production thereof and remain in the resin.
Epoxy resin compositions used in encapsulation, adhesion or the like of electrical and electronic parts have conventionally required a small content of impurities. That is, it is known that impurities in an epoxy resin composition have an adverse effect, such as deterioration of electrical insulating property or heat resistance of the cured resin,corrosion of lead wires or the like. In particular, in the case that an epoxy resin composition is used as an encapsulant resin of semiconductor integrated circuit, high purity is essential, and an acceptable amount of impurities is decreasing as the degree of integration of semiconductor circuit increases. Among various impurities, ionic impurities such as halogen compounds are considered to give most adverse effect, and an effort has been continued to exclude those impurities as much as possible. However, in recent years, it has also been required to decrease impurities other than ionic impurities.
An epoxy resin composition obtained by the reaction of 4,4′-dihydroxy-3,3′,5,5′-tetramethylbiphenyl represented by the following structural formula (3):
and an epihalohydrin, hereinafter referred to as “tetramethylbiphenyl type epoxy resin composition”, has excellent characteristics, such as high heat resistance, lowmelt viscosity, low stress, high adhesion, low moisture absorption and the like, and therefore is widely used as a resin for semiconductor encapsulant.
An attempt has been made to decrease ionic impurities even in the epoxy resin composition of this type, and an epoxy resin composition having a decreased amount of ionic impurities is already produced industrially.
However, since the tetramethylbiphenyl type epoxy resin composition is mainly used for encapsulation of the most advanced semiconductors, further improvement has been required in its characteristics.
In general, 4,4′-dihydroxy-3,3′,5,5′-tetramethylbiphenyl is produced by oxidative coupling of 2,6-xylenol. In the production, various by-products, such as tetramethyldiphenoquinone represented by the following structural formula (4):
and a phenol compound represented by the following structural formula (2):
are produced by side-reactions or the like, and included as impurities in the product 4,4′-dihydroxy-3,3′,5,5′-tetramethylbiphenyl.
Japanese Patent Application Laid-open No. Sho 61-268641 describes a production process whereby the by-product tetramethyldiphenoquinone can be decreased. However, tetramethyldiphenoquinone and/or the phenol compound represented by the structural formula (2) usually remain in industrially available 4,4′-dihydroxy-3,3′,5,5′-tetramethylbiphenyl products.
SUMMARY OF THE INVENTION
The present invention has an object to provide a high performance epoxy resin composition useful in electrical and electronic fields and the like, a process for producing the high performance epoxy resin composition, and a curable epoxy resin composition using the high performance epoxy resin composition.
As a result of various investigations to solve the above-mentioned problem, the present inventors have found that a tetramethylbiphenyl type epoxy resin composition having a low content of specific impurities has excellent heat resistance and electric characteristics and the like, and also have found that the tetramethylbiphenyl type epoxy resin composition having a low content of specific impurities can be obtained by using raw material having a low content of such specific impurities. As a result, the object has been attained.
The present invention includes:
(1) a tetramethylbiphenyl type epoxy resin composition comprising an epoxy resin composition obtained by reacting 4,4′-dihydroxy-3,3′,5,5′-tetramethylbiphenyl and an epihalohydrin in the presence of an alkali metal compound, wherein said composition has a content of tetramethyldiphenoquinone of 0.5% by weight or less;
(2) a tetramethylbiphenyl type epoxy resin composition comprising an epoxy resin composition obtained by reacting 4,4′-dihydroxy-3,3′,5,5′-tetramethylbiphenyl and an epihalohydrin in the presence of an alkali metal compound, wherein said composition has a content of a glycidyl compound represented by the following structural formula (1):
of 0.5% by weight or less;
(3) a tetramethylbiphenyl type epoxy resin composition, comprising an epoxy resin composition obtained by reacting 4,4′-dihydroxy-3,3′,5,5′-tetramethylbiphenyl and an epihalohydrin in the presence of an alkali metal compound, wherein the total content of tetramethyldiphenoquinone and the glycidyl compound represented by the above structural formula (1) is 0.8% by weight or less;
(4) a process for producing a tetramethylbiphenyl type epoxy resin composition having a content of tetramethyldiphenoquinone of 0.5% by weight or less, comprising reacting 4,4′-dihydroxy-3,3′,5,5′-tetramethylbiphenyl having a content of tetramethyldiphenoquinone of 0.5% by weight or less and an epihalohydrin in the presence of an alkali metal compound;
(5) a process for producing a tetramethylbiphenyl type epoxy resin composition having a content of a glycidyl compound represented by the following structural formula (1):
of 0.5% by weight or less, comprising reacting 4,4′-dihydroxy-3,3′,5,5′-tetramethylbiphenyl having a content of the phenol compound represented by the structural formula (2) of 0.5% by weight or less, and an epihalohydrin in the presence of an alkali metal compound;
(6) a process for producing a tetramethylbiphenyl type epoxy resin composition having the total content of tetramethyldiphenoquinone and the glycidyl compound represented by the above structural formula (1) of 0.8% by weight or less, comprising reacting 4,4′-dihydroxy-3,3′,5,5′-tetramethylbiphenyl having the total content of the tetramethyldiphenoquinone and the phenol compound represented by the above structural formula (2) of 0.8% by weight or less, and an epihalohydrin in the presence of an alkali metal compound; and
(7) a curable epoxy resin composition comprising a blend of the tetramethylbiphenyl type epoxy resin composition as described in any one of the aforementioned items (1) to (3), and an epoxy resin hardener for the epoxy resin, as essential components.
DESCRIPTION OF PREFERRED EMBODIMENTS
The high performance epoxy resin composition of the present invention is an epoxy resin composition obtained from 4,4′-dihydroxy-3,3′,5,5′-tetramethylbiphenyl and an epihalohydrin. The amount of tetramethyldiphenoquinone as an impurity in the resin is 0.5% by weight or less, preferably 0.3% by weight or less, more preferably 0.2% by weight or less.
The amount of the glycidyl compound represented by the structural formula (1):
as an impurity in the resin is 0.5% by weight or less, preferably 0.3% by weight or less, more preferably 0.2% by weight or less. Further, the total amount of the tetramethyldiphenoquinone and the glycidyl compound represented by the above structural formula (1) is 0.8% by weight or less, preferably 0.5% by weight or les
Aylward D.
Dawson Robert
Japan Epoxy Resins Co., Ltd.
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