JPH04202319A - Epoxy resin composition, cured epoxy resin and copper-clad laminated board - Google Patents

Abstract

PURPOSE:To provide the subject composition for copper-clad laminated board, etc., having high toughness, flexibility and impact resistance and containing a bisphenol A epoxy resin, a bisphenol A compound or a novolak resin as a hardener and a high-molecular weight polycarbonate as an additive. CONSTITUTION:The objective resin composition can be produced by compounding (A) a bisphenol A epoxy resin of formula (n is 0-10; m is 1; lis 0; R<1> and R<2> are glycidyl; A<1> to A<8> are H or Br) as a base resin, (B) a bisphenol A (bromide) of formula (n is 0; m is 1; l is 0; R<1> and R<2> are H; A<1> to A<8> are H or Br) or a novolak resin produced by bonding >=2 molecules of the bisphenol A (bromide) through methylene group at any of A<1> to A<8> as an epoxy resin hardener and (C) a high-molecular weight polycarbonate of formula (n is 0; m is 50-500; l is 1; B is CO; R<1> and R<2> are polymer terminal group; A<1> to A<8> are H or Br) as an additive.

Description

Detailed Description of the Invention [Field of Industrial Application] The present invention is directed to an epoxy resin composition containing a resin base having a bisphenol A type skeleton, an epoxy resin curing agent, and an additive, and particularly to an epoxy resin composition containing an epoxy resin that originally has a bisphenol A type skeleton. Epoxy resin compositions and cured products thereof, which further improve properties such as good adhesion and heat resistance, and have excellent toughness, flexibility, bending strength, impact resistance, and dimensional stability. The present invention relates to copper-clad laminates using.

[Conventional technology]

Epoxy resins have been used in a wide range of industrial fields due to their good adhesion and heat resistance.

Among them, glass epoxy copper-clad laminates used in printed wiring boards are being used not only for industrial purposes, but also for consumer use, where paper phenol copper-clad laminates have been the mainstay until now.

The epoxy resins (compositions) conventionally used for printed wiring boards include: 1) polyfunctional epoxy resins, novolac-type phenolic resins, and brominated polyP-vinylphenol, with improved flame resistance and flame resistance (special 1977-
112924), ■ Epoxy resin blended with phenol novolac resin to improve heat resistance, solvent resistance, etc. (JP-A-57-109642), ■ Epoxy resin and para-secondary butylphenol/phenol co-condensed novolak A product in which heat resistance and solvent resistance are improved by blending a resin (JP-A-57-190025), ■An epoxy resin composition is reacted with bisphenol A type epoxy resin, tetrabromobisphenol A, and a polyfunctional epoxy resin. (Japanese Unexamined Patent Publication No. 167044/1983), which has improved heat resistance by blending a brominated epoxy resin produced by
Brominated epoxy resin mixed with N, N, N', N'-tetraglycidyl-4,4'-diaminophenylmethane to improve flammability (Japanese Unexamined Patent Publication No. 17701/1986)
No. 4).

However, as printed wiring boards become more dense and multi-layered, the current situation is that conventional boards using epoxy resins are no longer fully satisfactory.

For example, conventional epoxy resins are fully satisfactory in adhesion strength to copper foil at room temperature, but at 100°C
At higher temperatures, the strength rapidly decreases, which poses a problem in terms of reliability for high-density wiring boards with extremely fine patterns.

In other words, in the reflow process, which is the flow of mounting components on a board, the temperature of the board becomes high in parts due to the use of infrared rays, etc., and the number of reflows tends to increase. In,
There is a problem that problems such as peeling of the patterned copper foil occur. Moreover, some of the parts in the negative part partially raise the temperature of the board to 100 DEG C. or more, and there is also a problem in the board on which such parts are mounted.

In addition, with the spread of IC cards and the reduction in the weight of devices, the thickness of substrates has become noticeably thinner.Therefore, there is a need for strong substrates with high strength, especially bending strength, but conventional epoxy resin When using a substrate, there are also problems with the strength of the substrate, such as breakage when subjected to repeated bending loads.

Furthermore, as density increases, higher dimensional accuracy becomes necessary, but conventional copper-clad laminates using epoxy resin have the problem of large dimensional changes during the manufacturing process.

In this way, as the pattern width becomes narrower due to higher density,
Improved adhesion between the copper foil and the substrate and high dimensional accuracy are required from the viewpoint of reliability as well as heat resistance. In addition, as devices become lighter, thinner, shorter, and smaller, substrates become thinner, and improvements in bending strength and flexibility are required. Therefore, there is a need for epoxy resin and copper-clad laminates that can fully meet these demands.

[Problem to be solved by the invention]

The purpose of the present invention, in order to meet the above-mentioned demands, is to have excellent heat resistance and adhesion, and therefore high adhesion strength between copper foil and resin at high temperatures, as well as excellent flexibility, impact resistance, and dimensional stability. It is an object of the present invention to provide a strong epoxy resin composition that also has high bending strength.

Other objects of the present invention are heat resistance, adhesion, flexibility,
It is an object of the present invention to provide a tough epoxy resin cured product that has excellent impact resistance and dimensional stability, and also has high bending strength.

Another object of the present invention is that by using the epoxy resin composition, the adhesion strength between the copper foil and the composite material at high temperatures is high, and furthermore, it has excellent impact resistance and dimensional stability, and has flexural strength. The purpose of the present invention is to provide a copper-clad laminate with high toughness.

[Means to solve the problem]

The present invention relates to the following epoxy resin composition, cured epoxy resin, and copper-clad laminate.

(1) (A) As the resin main agent, use the following - saccharide [1] (where n is O to 10, m is 1, Q is 0. R' and R' are glycidyl groups, A1 to A'' are hydrogen atoms or Bisphenol A-based epoxy resin represented by (bromine atom), and (
B) As an epoxy resin curing agent.

(b2) Below - Murder [1] (However, n is 0.m is 1,
Bisphenol A represented by Q is 0, R' and R2 are hydrogen atoms, A1 to A4 are hydrogen atoms or bromine atoms)
or a bromide thereof, or (b2) represented by the following -Sakatsu [1] (where n is 0, m is 1, Q is 0, R1 and R2 are hydrogen atoms, A1 to A4 are hydrogen atoms or bromine atoms) Bisphenol A
Or with a novolak resin of bisphenol A or its brominated product, in which two or more molecules of its brominated product are bonded via a methylene group at any of the positions A1 to A4.

(C) As an additive, use the following -Katsu [1] (where n is 0, m is 50-150, Q is 1, B is -C-1R1 and R2 are polymer terminal groups, A1 to A4 are hydrogen atoms or a bromine atom).

(2) (A) As the resin main ingredient, the above-mentioned -Kabuki [1] (However.

n is 0 to 10. A bisphenol A-based epoxy resin in which m is 1, Q is 0, R1 and R2 are glycidyl groups, and A1 to A'' are hydrogen atoms or bromine atoms.

(B) As an epoxy resin curing agent, (b2) the above-mentioned -Katsu [1] (where n is 0, m is 1,
Q is 0, R'' and R2 are hydrogen atoms, A1 to A' are hydrogen atoms or bromine atoms), or (b2) the above-mentioned -Katsu [1] (where n is 0 , m is 1,
Q is 0. Bisphenol A represented by R1 and R2 are hydrogen atoms, A1 to A4 are hydrogen atoms or bromine atoms)
or a novolak resin of bisphenol A or its bromide, in which two or more molecules of its bromide are bonded via methylene groups at any of the positions A1 to A4; n is 0, m is 50 to 150, Q is 1, B is -C-1R1 and R2 are polymer terminal groups, and A1 to A4 are hydrogen atoms or bromine atoms). An epoxy resin containing a high molecular weight polycarbonate. A cured epoxy resin obtained by curing the composition.

(3) A copper-clad laminate in which copper foil is laminated on one or both sides of a composite material obtained by impregnating and curing the epoxy resin composition described in (1) above into a fiber base material.

The resin base (A) used in the present invention is the above-mentioned
] (where n is O to 10, m is 1, Q is 0, R1 and R2 are glycidyl groups, and A1 to A' are hydrogen atoms or bromine atoms). This bisphenol-based epoxy resin is
It may be a bisphenol A type epoxy resin in which A1 to A6 in 13 are hydrogen atoms, or it may be a brominated epoxy resin in which at least one of A1 to A8 is a bromine atom and the rest are hydrogen atoms. Brominated epoxy resins are selected when flame retardancy is required. Such bisphenol-based epoxy resins are 1 usually the most widely used bisphenol A-based epoxy resin.

As the bisphenol A-based epoxy resin used in the present invention, diglycidyl ether obtained by reacting bisphenol Δ and/or halogenated bisphenol A with epichlorohydrin can be used. Commercially available products can also be used, such as Epicote 828 (R1 and R2 in the above-mentioned -Kakuretsu (1) are glycidyl groups, n is about 0.1, m is 1, Q is O, and A1 to A'' are hydrogen atoms), Epicote 10
01 (R1 and R2 of the above-mentioned -Sakatsu [1] are glycidyl groups, n is about 2.0, m is 1, Q is 0, A1 to A'' are hydrogen atoms), Epicoat 1004 (of the above-mentioned -Sakatsu [1]) R''
and R2 is a glycidyl group, n is about 4.4, m is 1, Q
is O, A' to A' are hydrogen atoms), Epicoat 5046
(R1 and R2 of the above-described m are glycidyl groups, n is about 1.4, m is 1.0 is O, A' to A' are hydrogen atoms, A
``'' to A', 2 of which are bromine atoms and the rest are hydrogen atoms), and Epicoat 5050 (R1 and R2 of the above-mentioned -Katsu (1), 1 glycidyl group, n is about 1.3, m is 1, Q is O, Ai to A@ is a bromine atom) (all are trade names manufactured by Yuka Shell Epoxy Co., Ltd.), and the like.

These bisphenol A-based epoxy resins may be used alone or in combination.

As the resin base (A), a non-bisphenol A epoxy resin may be mixed with the bisphenol A epoxy resin to the extent that the object of the present invention is not impaired.

The epoxy resin curing agent (B) used in the present invention is the above-mentioned -Kiroku [1] (where n is 0, m is 1, and Q is 01R1).
and R2 is a hydrogen atom, A1 to A4 are hydrogen atoms or bromine atoms), or bisphenol A or its bromide (b2), or the above-mentioned
n is 0, m is 1, Q is 0, R1 and R2 are hydrogen atoms,
Bisphenol A or its brominated product represented by A゛~A4 is a hydrogen atom or a bromine atom) is A1~A4
It is a novolac resin (b2) of bisphenol A or its brominated product, in which two or more molecules are bonded by methylene groups at any position.

The epoxy resin curing agent CB) has bisphenol A as its skeleton, similar to the epoxy resin as the resin base (A).
It is characterized by having a molded skeleton, which gives it toughness and heat resistance. If further heat resistance is required, bisphenol A or its brominated novolak resin is selected.

As the epoxy resin curing agent (B) used in the present invention, 2,2-bis(4-hydroxyphenyl)propane (
R1 and R2 of the above-sadatsu [1] are hydrogen atoms, and n is 0
, m is 1.0 is O, A1 to A' are hydrogen atoms), 2,2-
Bis(3,5-dibromo-4-hydroxyphenyl)propane (R1 and R2 of the above-described [1] are hydrogen atoms, n is 0, m is 1, Q is o, A1 to A4 are bromine atoms) and them Examples include novolac resins having a phenol component (two or more molecules bonded by a methylene group at any of A1 to A4 in the general formula [1]).

The additive (C) used in the present invention has the above general formula [1]
(However, n is 0, m is 50-150, Q is 1, B is -
C-1R1 and R2 are polymer terminal groups, and A1 to A4 are hydrogen atoms or bromine atoms), which is a high molecular weight polycarbonate. Examples of the polymer terminal group include an alkyl group and an alkyl hydroxide group.

In the present invention, the additive (C) is also the resin base material (A).
And, like the epoxy resin curing agent (B), it is characterized by having a bisphenol A type skeleton. This not only imparts toughness and heat resistance, but also greatly improves impact resistance and one-dimensional stability due to the action of the high molecular weight polycarbonate.

Since the high molecular weight polycarbonate used as the additive (C) is a high molecular weight linear polymer, it is extremely difficult to mix it uniformly with ordinary resins, curing agents, etc., but in the present invention, Since the basic molecular structures of the main resin (A), epoxy resin curing agent (B), and additive (C) are the same, these three components can be mixed sufficiently uniformly without causing microscopic layer separation. be done.

As the additive (C) used in the present invention, commercially available products can also be used. For example, Taflon A2200 (general formula [1]
R1 and R2 are polymer terminal groups such as an alkyl group or an alkyl hydroxide group, n is O, Q is 1, and -C-1m is about 85. A1 to A' are hydrogen atoms), Taflon A3000 (R1 and R of the general formula [1] above)
2 is a polymer terminal group such as an alkyl group or an alkyl hydroxide group, n is O, Q is 1, B is -G-, m is about 115, A1
~A4 is a hydrogen atom), and Taflon NB2500 (
In the general formula [l], 81 and R2 are a polymer terminal group such as an alkyl group or an alkyl hydroxide group, n is O, Q is 1, and B is -C-1m is about 96. A'' to A4 are hydrogen atoms and bromine atoms) (all manufactured by Idemitsu Petrochemical Co., Ltd., trade names), and the like.

The greatest feature of the epoxy resin composition of the present invention is that the resin base (A), the epoxy resin curing agent (B), and the additive (C) all have the same bisphenol A type skeleton. ing. In other words, the epoxy resin base material (
A), epoxy resin curing agent (8), and additive (C) have the same basic molecular structure (bisphenol A type), so they mix at the molecular level and do not cause microscopic layer separation. Therefore, as a result, a strong epoxy resin composition having high heat resistance and adhesion strength, excellent impact resistance and dimensional stability, and high bending strength can be obtained.

In the case of epoxy resin compositions (using components that do not have the same basic molecular structure), it is extremely difficult to mix each component uniformly, and even if a uniformly dissolved resin composition is mixed with sufficient mechanical stirring, Even if this is achieved, microscopic layer separation may occur during long-term storage or prepreg manufacturing, resulting in a decrease in heat resistance and insufficient improvement in adhesion, impact resistance, 1-dimensional stability, etc. or

A catalyst can be used in the epoxy resin composition of the present invention in the same manner as in ordinary epoxy resins. Suitably used catalysts include 2-methylimidazole and 2-ethyl-
Imidazole compounds such as 4-methylimidazole, l-benzyl-2-methylimidazole, 2-phenylimidazole, 2-undecylimidazole, 2-heptadecyl imidazole, tetraethylamine, benzyldimethylamine, 2,4゜6-tris( Examples include tertiary amine compounds such as dimethylaminomethyl)phenol, dicyandiamide and its derivatives, and BF□-monoethylamine.

Further, solvents can be used in the epoxy resin composition of the present invention, such as chloroform, methylene chloride, tetrachloroethane, dioxane, 1.degree. 2-dichloroethane, and 1,1.2-trichloroethane. These solvents may be used alone or in combination of two or more.

Furthermore, the epoxy resin composition of the present invention can also contain other additives such as fillers, dyes, and pigments used in ordinary epoxy resins.

The respective compounding ratios of the main resin (A), the epoxy resin curing agent (B), and the additive (C) in the epoxy resin composition of the present invention are not particularly limited; ) is suitable in terms of the properties of the cured product. Also(
C) is 0.1 to 2% by weight relative to (A) + (B)
A range of 0% is preferred. That is, heat resistance, impact resistance 1
If dimensional stability is important, a large amount of (C) may be added.

The epoxy resin composition of the present invention includes (A), (B) and (
It is produced by mixing each component of C) and other added components.

The epoxy resin composition of the present invention thus obtained can be used as it is in the same way as conventional epoxy resins, but the epoxy resin composition of the present invention can also be used as an additive to other epoxy resins. It can also be added to improve the properties of the epoxy resin after addition. However, in that case, the epoxy resin composition of the present invention as an additive has a
It is necessary to use at least 10 parts by weight61
Less than 0 parts by weight, ゛ is the desired adhesion strength, toughness,
No significant effect was observed in improving impact resistance, 1-dimensional stability, etc.

The epoxy resin composition of the present invention can be used in the same fields as conventional epoxy resins, but it has excellent heat resistance, adhesion, flexibility, impact resistance, dimensional stability, bending strength, etc. Therefore, it is suitably used in fields where such characteristics are required.

The cured epoxy resin of the present invention is obtained by curing the epoxy resin composition. The cured epoxy resin can be produced by heating in the same manner as conventional epoxy resins.

The copper-clad laminate of the present invention includes impregnating the epoxy resin composition into a fiber base material such as glass cloth, glass mat, or aramid cloth.
Copper foil is laminated on one or both sides of a cured composite material.

Such a copper-clad laminate can be manufactured in the same manner as a conventional epoxy resin copper-clad laminate.

That is, a fiber base material such as glass cloth, glass mat or aramid cloth is directly impregnated with the resin composition of the present invention without a solvent, or it is temporarily dissolved in a solvent to form a varnish, and this is impregnated into the fiber base material. After that, only the solvent is removed to form a so-called prepreg, and then copper foil is laminated on one or both sides of the prepreg, and the resin is cured by heating, pressurizing, etc. to produce the prepreg.

The copper-clad laminate thus obtained has high adhesion strength between the copper foil and the composite material at high temperatures, has excellent impact resistance, dimensional stability, and heat resistance, and is strong with high bending strength.

Such a copper-clad laminate can be used as a substrate for printed wiring boards and the like.

(Example〕 Next, the present invention will be specifically explained using examples.

Example 1 Epicoat 828 (manufactured by Yuka Shell Epoxy Co., Ltd., epoxy equivalent: 180-190, trade name) was used as the resin base (A), and 2,
2-bis(4-hydroxyphenyl)propane novolak (phenol equivalent: 150) was converted into a phenol equivalent/epoxy equivalent ratio (hereinafter referred to as PE/EE ratio) of 0.85.
Taflon^2200 (manufactured by Idemitsu Petrochemical Co., Ltd., trade name) was added as an additive (C) to the mixture as follows.
was added in an amount of 10% by weight based on the resin base (A) and the epoxy resin curing agent (B), and 2-ethyl-4 was added as a catalyst.
An epoxy varnish was obtained by dissolving 0.1% by weight of methylimidazole based on other resin components in 1,2-dichloroethane to a solid content of 50%.

This was impregnated into a glass woven fabric with a thickness of 0.18 mm and dried to obtain a prepreg with a resin content of 50% by weight. Four sheets of this prepreg were stacked and press-molded with 354 copper foils interposed on both sides. The molding conditions were a press temperature of 180° C., a press pressure of 40 kg/a, and a press time of 90 minutes. Table 1 shows the evaluation results regarding the characteristics of this copper-clad laminate.

Example 2 Copper was prepared in the same manner as in Example 1, except that Epicoat 5046 (manufactured by Yuka Shell Epoxy Co., Ltd., epoxy equivalent: 480, trade name) was used as the resin base (A), and benzyldimethylamine was used as the catalyst. A stretched laminate was obtained.

Table 1 shows the evaluation results regarding the characteristics.

Example 3 Epicoat 1001 (manufactured by Yuka Shell Epoxy Co., Ltd., epoxy equivalent: 450-500, trade name) was used as the resin base (A), and the PE/EE ratio was 0.95. Additive (C
) A copper-clad laminate was obtained in the same manner as in Example 1, except that 5% by weight of Taflon NB2500 (manufactured by Idemitsu Petrochemical Co., Ltd., trade name) was used. Table 1 shows the evaluation results regarding its characteristics.
Shown below.

Example 4 Non-bisphenol A-based polyfunctional epoxy resin TACTIX-742 (manufactured by Dow Chemical Company, epoxy equivalent: 162. Trade name) and Epicoat 5046 were used as the resin base (A).
(manufactured by Yuka Shell Epoxy Co., Ltd., epoxy equivalent: 460~
490 (trade name) in a weight ratio of 1:1, and 2,2-bis(4-hydroxyphenyl)propane novolak (phenol equivalent 180) was used as the epoxy resin curing agent (B). The additive (C) was Taflon A2200 (manufactured by Idemitsu Petrochemical Co., Ltd., trade name), and the resin base material (A) was mixed with the epoxy resin curing agent (B) so that the EE ratio was 0.90. ) for 10
% by weight, and 2-phenylimidazole as a catalyst is added to the resin base (A) and the epoxy resin curing agent (8).
0.15% by weight of the solids was dissolved in 1,2-dichloroethane to give a solid content of 55% by weight.

Obtained epoxy varnish.

This was impregnated into a glass woven fabric having a thickness of 0.18 mm and dried to obtain a prepreg having a resin content of 48% by weight. Four sheets of this prepreg were stacked and press-molded with 35 Im thick copper foil interposed on both sides. The molding conditions were a press temperature of 180°C, a press pressure of 40 kg/cd, and a press time of 90 minutes. Table 1 shows the evaluation results regarding the characteristics of this copper-clad laminate.

Comparative Example 1 Example except that no bisphenol A-based epoxy resin was used and only non-bisphenol A-based polyfunctional epoxy resin EPPN-502 (manufactured by Nippon Kayaku Co., Ltd., epoxy equivalent 160-180, trade name) was used. A copper-clad laminate was obtained in the same manner as in 4. However, this laminate had a cloudy appearance compared to Examples 1 to 4. This is probably due to layer separation of the additive (C) during prepreg production. Table 1 shows the evaluation results regarding the characteristics.

Comparative Example 2 A copper-clad laminate was obtained in the same manner as in Example 4, except that 20 parts by weight of diaminodiphenylsulfone was added as the epoxy resin curing agent (B) to 100 parts by weight of the resin base (A). However, this laminate had a cloudy appearance compared to Examples 1 to 4. Table 1 shows the evaluation results regarding the characteristics.

Comparative Example 3 A copper-clad laminate was obtained in the same manner as in Example 4 except that the additive (C) was omitted. Although the appearance of this laminate was as good as Examples 1 to 4, it was inferior in copper foil adhesive strength and the like. Table 1 shows the evaluation results regarding the characteristics.

As shown in the above examples, the epoxy resin composition of the present invention and the copper-clad laminate obtained therefrom contain a resin base (A), an epoxy resin curing agent (8), and an additive (C).
Because both of these materials have a bisphenol A type skeleton, they are mixed at the molecular level and have heat resistance, adhesion, toughness, impact resistance, and dimensional stability.

〔Effect of the invention〕

As described above, according to the present invention, each of the resin base material (A), the epoxy resin curing agent CB), and the additive (C),
Since we used a material with a bisphenol A type skeleton, it has excellent heat resistance and adhesive properties, and therefore has high adhesion strength between the copper foil and resin at high temperatures, as well as excellent flexibility and impact resistance. A tough epoxy resin composition with excellent dimensional stability and high bending strength can be obtained.

Further, according to the present invention, a tough epoxy resin cured product having excellent heat resistance, adhesion, flexibility, impact resistance, and one-dimensional stability as well as high bending strength can be obtained.

Furthermore, according to the present invention, by using the above-mentioned epoxy resin composition, the adhesion strength between the copper foil and the composite material at high temperatures is high, and furthermore, it has excellent impact resistance, dimensional stability, and strong bending strength. A copper-clad laminate is obtained.

Claims (3)

[Claims] (1) (A) As the main resin, the following general formula [1] (where n is 0 to 10, m is 1, l is 0, R^1 and R^
2 is a glycidyl group, A^1 to A^8 are hydrogen atoms or bromine atoms), a bisphenol A-based epoxy resin represented by (B) an epoxy resin curing agent, (b1) the following general formula [1] (however, n is 0, m is 1,
l is 0, R^1 and R^2 are hydrogen atoms, A^1~A^
4 is a hydrogen atom or a bromine atom), or (b2) the following general formula [1] (where n is 0, m is 1,
l is 0, R^1 and R^2 are hydrogen atoms, A^1~A^
4 is a hydrogen atom or a bromine atom), and bisphenol A or its brominated product is a novolac resin of bisphenol A or its brominated product, in which two or more molecules of bisphenol A or its brominated product are bonded by a methylene group at any of the positions A^1 to A^4. (C) As an additive, the following general formula [1] (where n is 0, m is 50 to 250, l is 1, B is ▲ mathematical formula, chemical formula,
▼, R^1 and R^2 are polymer terminal groups, and A^1 to A^4 are hydrogen atoms or bromine atoms) An epoxy resin characterized by containing a high molecular weight polycarbonate. Composition. ▲There are mathematical formulas, chemical formulas, tables, etc.▼・・・[1] (2) (A) As the main resin, the following general formula [1] (where n is 0 to 10, m is 1, l is 0, R^1 and R^
2 is a glycidyl group, A^1 to A^8 are hydrogen atoms or bromine atoms), a bisphenol A-based epoxy resin represented by (B) an epoxy resin curing agent, (b1) the following general formula [1] (however, n is 0, m is 1,
l is 0, R^1 and R^2 are hydrogen atoms, A^1~A^
4 is a hydrogen atom or a bromine atom), or (b2) the following general formula [1] (where n is 0, m is 1,
l is 0, R^1 and R^2 are hydrogen atoms, A^1~A^
4 is a hydrogen atom or a bromine atom), and bisphenol A or its brominated product is a novolac resin of bisphenol A or its brominated product, in which two or more molecules of bisphenol A or its brominated product are bonded by a methylene group at any of the positions A^1 to A^4. (C) As an additive, the following general formula [1] (where n is 0, m is 50 to 150, l is 1, B is ▲ mathematical formula, chemical formula,
There are tables, etc. ▼, R^1 and R^2 are polymer terminal groups, and A^1 to A^4 are hydrogen atoms or bromine atoms). A cured epoxy resin product characterized by: ▲There are mathematical formulas, chemical formulas, tables, etc.▼・・・[1] (3) A copper-clad laminate, characterized in that copper foil is laminated on one or both sides of a composite material obtained by impregnating and curing the epoxy resin composition according to claim (1) into a fiber base material.