JP2001329044A - Epoxy resin composition and its cured product - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a novel epoxy resin composition which produces a cured product having an excellent storage stability, humidity resistance, and excellent electrical characteristics. SOLUTION: The epoxy resin composition and its cured product comprise an epoxy resin having a structure which is obtained by reacting a specific aromatic diol having a phenylenedialkylene skeleton in a molecule with an epihalohydrin and a curing agent as essential components.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an epoxy resin and an epoxy resin composition which give a cured product having excellent moisture resistance and electrical properties, and a cured product thereof.

[0002]

2. Description of the Related Art Epoxy resins can be cured with various curing agents to give cured products having generally excellent mechanical properties, moisture resistance, chemical resistance, heat resistance, electrical properties, and the like. It is used in a wide range of fields, such as laminates, molding materials, and casting materials. Conventionally, there is a liquid or solid bisphenol A type epoxy resin obtained by reacting bisphenol A with epichlorohydrin as the epoxy resin most used industrially.

[0003]

However, the above-mentioned general-purpose epoxy resin does not reach the level where the storage stability of the composition and the moisture resistance and the electrical properties of the cured product have reached satisfactory levels. In the field of sealing materials, printed wiring boards, and powder coatings, high-performance epoxy resin compositions having better storage stability, moisture resistance, and electrical properties have been desired.

[0004]

Means for Solving the Problems In view of such circumstances, the present inventors have conducted intensive studies on an epoxy resin composition which gives a cured product having excellent moisture resistance and electric properties. As a result, the epoxy resin composition is represented by the following formula (1). It has been found that an epoxy resin composition using, as a curing agent, an epoxy resin having a structure obtained by reacting a compound with epihalohydrin satisfies these requirements, and has completed the present invention.

That is, the present invention provides the following formula (1)

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(Wherein, n represents an average value and 0 <n ≦
Take the value of 10. A represents a phenylene group, a divalent biphenylene group, an alkylenediphenyl group, an oxydiphenyl group,
A benzophenone residue, a divalent naphthalene group, an alkylenedinaphthyl group, a binaphthyl group, or a diphenylsulfone residue, B is a divalent hydrocarbon group, R is a hydrogen atom, a halogen atom, or an alkyl having 1 to 8 carbon atoms. R represents an aryl group or an aryl group, and each R may be the same or different from each other. An epoxy resin composition comprising an epoxy resin obtained by reacting the compound represented by the formula (1) with epihalohydrin, and a curing agent as essential components,

In the equation (1), A is the equation (2)

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Wherein X represents a hydrocarbon group having 1 to 14 carbon atoms, a carbonyl group, a sulfone group, or a direct bond; R represents a hydrogen atom, a halogen atom, an alkyl group having 1 to 8 carbon atoms,
Represents an aryl group, and each R may be the same or different from each other. ),

Equation (3)

[0010]

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(In the formula, R represents a hydrogen atom, a halogen atom, an alkyl group having 1 to 8 carbon atoms or an aryl group.
May be the same or different from each other. ),

Equation (4)

[0013]

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Or equation (5)

[0015]

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An epoxy resin composition as described above,

An epoxy resin composition comprising, as essential components, the above-mentioned or the above-mentioned epoxy resin wherein B in the formula (1) is a methylene group, and a curing agent;

X in the formula (2) is the formula (6),

[0019]

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Or equation (7),

[0021]

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The epoxy resin composition as described above or described above,

The epoxy resin obtained by reacting the compound represented by the formula (1) with epihalohydrin has an epoxy equivalent in the range of 250 to 600 g / equivalent. Epoxy resin composition,

[0024] The present invention provides a cured product obtained by curing the epoxy resin composition according to any one of the above.

[0025]

BEST MODE FOR CARRYING OUT THE INVENTION The compound represented by the formula (1) is, for example, a compound represented by the formula (8)

[0026]

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(Y is a halogen atom selected from chlorine, bromine and iodine, R is a hydrogen atom, a halogen atom, and has 1 to 8 carbon atoms.
And the individual Rs may be the same or different from each other. ) And a bifunctional phenol are subjected to a dehydrohalogenation condensation reaction.

Specific examples of the compound represented by the formula (8) include α, α'-xylenedichloride, bis (α-chloroethyl) benzene, bis (2-chloroethyl) benzene, bis (chloropropyl) benzene , Bis (3-chlorobutyl) benzenes or alkyl-substituted bis (haloalkyl) benzenes, and α, α'-xylene dichloride is particularly preferred from the viewpoint of ease of reaction.

Specific examples of the dihydric phenols used include bisphenol A, bisphenol F, fluorene bisphenol, bis (4-hydroxyphenyl) menthane, bis (4-hydroxyphenyl) dicyclopentane, 4,4'-dihydroxy Benzophenone, bis (4
-Hydroxydiphenyl) ether, bis (4-hydroxy-3-methylphenyl) ether, bis (3,5-dimethyl-4-hydroxyphenyl) ether, bis (4
-Hydroxyphenyl) sulfide, bis (4-hydroxy-3-methylphenyl) sulfide, bis (3,5
-Dimethyl-4-hydroxyphenyl) sulfide, bis (4-hydroxyphenyl) sulfone, bis (4-hydroxy-3-methylphenyl) sulfone, bis (3
5-dimethyl-4-hydroxyphenyl) sulfone,
1,1-bis (4-hydroxyphenyl) cyclohexane, 1,1-bis (4-hydroxy-3-methylphenyl) cyclohexane, 1,1-bis (3,5-dimethyl-4-hydroxyphenyl) cyclohexane, , 1 '
Bisphenols such as -bis (3-t-butyl-6-methyl-4-hydroxyphenyl) butane;

Benzenediols such as hydroquinone, ditertiary butyl hydroquinone, resorcinol, catechol and tertiary butyl catechol;

Equation (9)

[0032]

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(R is a hydrogen atom, a halogen atom, carbon number 1
To 8 alkyl groups or aryl groups,
Each R may be the same or different from each other. Biphenol, tetramethylbiphenol, 4,4'-dihydroxybiphenyl-3,3 ',
Biphenols such as 5,5'-tetramethylbiphenyl,

Equation (10)

[0035]

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1,2-dihydroxynaphthalene, 2,3-dihydroxynaphthalene, 1,4-dihydroxynaphthalene,

Equation (11),

[0038]

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Dihydroxynaphthalenes such as 1,5-dihydroxynaphthalene, 1,6-dihydroxynaphthalene, and 2,7-dihydroxynaphthalene represented by

Equation (12)

[0041]

Embedded image (In the formula, W represents a hydrocarbon group having 1 to 14 carbon atoms.)

Bis (hydroxynaphthyl) alkanes such as bis (hydroxynaphthyl) methane represented by

Alternatively, there may be mentioned, but not limited to, binaphthalenediols such as 1,1'-binaphthol.

Among the above dihydric phenols, bisphenol A, bisphenol F, dihydroxynaphthalenes,

Or equation (13)

[0046]

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(R is a hydrogen atom, a halogen atom, carbon number 1
To R 8 represents an alkyl group or an aryl group, and each R may be the same or different. A bisphenol compound derived from dicyclopentadiene and phenols represented by

[0048]

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(R is a hydrogen atom, a halogen atom, carbon number 1
To R 8 represents an alkyl group or an aryl group, and each R may be the same or different. Bisphenol compounds derived from fluorene and phenols represented by) are preferred because of their excellent heat resistance, moisture resistance and electrical properties, and particularly preferred are the dicyclopentadiene-type bisphenols because these properties are particularly excellent. Things.

When the above-mentioned dihydric phenols are, for example, bisphenol F or a compound represented by the formula (13), they are contained in a phenol novolak resin or a dicyclopentadiene phenol polyaddition resin in a mixture having a repeating structure. Can also be used. In this case, it is preferable to use a dihydric phenol having a content of 50% by weight or more, particularly preferably 80% by weight or more, so that the viscosity does not increase and the flowability and workability are not hindered. is there.

When the condensation reaction of the above dihydric phenol with the compound represented by the formula (8) is carried out, the amount of the compound represented by the formula (8) is usually 0 to 1 mol of the dihydric phenol. 0.1 to 0.9 mol, preferably 0.3 to 0.7 mol. If the amount of the compound represented by the formula (8) is small, the group represented by the formula (15) in the target epoxy resin

[0052]

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(B represents a divalent hydrocarbon group having 1 to 10 carbon atoms, R represents a hydrogen atom, a halogen atom, an alkyl group having 1 to 8 carbon atoms, or an aryl group; Or may be different.)

Content is low, the viscosity is low and the fluidity and workability are good, but the effect of improving storage stability, moisture resistance and electrical properties is small. On the other hand, when the amount of the compound represented by the formula (8) is high, the content of the group represented by the formula (15) in the target epoxy resin is increased, and the storage stability, moisture resistance, and electric properties are improved. Although the effect is increased, the viscosity is increased and the fluidity and workability are reduced. Therefore, the amount of the compound represented by the formula (8) may be appropriately adjusted depending on the required properties of desired viscosity, storage stability, moisture resistance, and electrical properties.

In the above reaction, a dehydrohalogenating agent is preferably present. Examples of the dehalogenating agent include alkali metal hydroxides such as sodium hydroxide, potassium hydroxide and lithium hydroxide, and triethylamine and the like. Tertiary amines can be used, but sodium hydroxide,
Potassium hydroxide is preferred from the viewpoint of the reaction rate. The amount of the dehydrohalogenating agent used is not particularly limited, but may be 2.0 to 1 mol of the compound represented by the formula (8).
It is preferred to use up to 3.0 moles. At that time, the reaction rate can be increased by using a phase transfer catalyst such as a quaternary ammonium salt or crown ether.

The above reaction is preferably performed in the presence of an organic solvent. Specific examples when using an organic solvent include methanol, ethanol, isopropyl alcohol, methyl cellosolve, ethyl cellosolve, toluene, xylene, methyl ethyl ketone, methyl isobutyl ketone, and the like. The amount of the organic solvent to be used is generally 50 to 300 parts by weight, preferably 70 to 250 parts by weight, based on 100 parts by weight of the total weight of the charged raw materials. The reaction temperature is usually 40
To 120 ° C., and the reaction time is usually 1 to 10 hours. These solvents can be used alone or as a mixture of several types.

For the reaction, for example, a dihydric phenol and a compound represented by the formula (8) are dissolved in an appropriate organic solvent, and a dehydrohalogenating agent is added dropwise thereto, and stirring is continued until the reaction is completed. After completion of the reaction, p of the water washing solution of the reaction mixture
An acidic compound such as sodium phosphate is added to neutralize the system so that the H value becomes 3 to 7. Then, after performing a water-washing treatment to remove the inorganic salt from the inside of the system, the organic solvent is recovered by distillation to obtain a dihydric phenol compound represented by the formula (1) which is an intermediate of the target epoxy resin. it can.

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(Wherein, n represents an average value and takes a value of 0 <n ≦ 10. A represents a phenylene group, a divalent biphenylene group,
An alkylenediphenyl group, a benzophenone residue, an oxydiphenyl group, a divalent naphthalene group, an alkylenedinaphthyl group, a binaphthyl group, or a diphenylsulfone residue, B is a divalent hydrocarbon group, R is a hydrogen atom, a halogen atom , An alkyl group or an aryl group having 1 to 8 carbon atoms, and each R may be the same or different. )

As a method for obtaining the epoxy resin of the present invention from the dihydric phenol compound represented by the formula (1), for example, a method known per se can be adopted. For example, an alkali metal hydroxide such as sodium hydroxide or potassium hydroxide is added to a dissolved mixture of the dihydric phenol compound represented by the formula (1) obtained above and epihalohydrin such as epichlorohydrin and epibromohydrin. Or while adding 2
The epoxy resin used in the present invention can be obtained by reacting at 0 to 120 ° C. for 1 to 10 hours.

The amount of epihalohydrin to be added is usually 0.1 to 1 equivalent of the hydroxyl group in the starting dihydric phenol compound.
A range of 3 to 20 equivalents is used. When the epihalohydrin is less than 2.5 equivalents, the epoxy group and the unreacted hydroxyl group are liable to react with each other, so that a group formed by the addition reaction between the epoxy group and the unreacted hydroxyl group (-CH ₂ CR (OH) CH _2- , R: a hydrogen atom or an alkyl group).
On the other hand, when it is more than 2.5 equivalents, the content of the theoretical structure becomes high. The amount of epihalohydrin may be appropriately adjusted depending on the desired properties.

In the reaction for obtaining the epoxy resin used in the present invention, an aqueous solution of the alkali metal hydroxide may be used. In this case, the aqueous solution of the alkali metal hydroxide is continuously added to the reaction system. At the same time, a method may be used in which water and epihalohydrin are continuously distilled off under reduced pressure or normal pressure, liquids are separated, water is removed, and epihalohydrin is continuously returned into the reaction system.

A quaternary ammonium salt such as tetramethylammonium chloride, tetramethylammonium bromide or trimethylbenzylammonium chloride is added as a catalyst to a dissolved mixture of the compound represented by the formula (1) and epihalohydrin at 50 to 150 ° C. A solid or aqueous solution of an alkali metal hydroxide is added to the halohydrin etherified compound of the compound of the formula (1) obtained by reacting for 1 to 5 hours, and the mixture is again reacted at 20 to 120 ° C. for 1 to 10 hours to remove halogen. A method of hydrogenation (ring closure) may be used. Further, in order to smoothly proceed the reaction, methanol, ethanol, isopropyl alcohol, alcohols such as butanol, acetone, ketones such as methyl ethyl ketone, ethers such as dioxane, dimethyl sulfone,
The reaction is preferably performed by adding an aprotic polar solvent such as dimethyl sulfoxide. When a solvent is used, its amount is usually 5 to 50 parts by weight, preferably 10 to 30 parts by weight, per 100 parts by weight of epihalohydrin. When an aprotic polar solvent is used, it is usually 5 to 100 parts by weight, preferably 10 to 60 parts by weight, per 100 parts by weight of epihalohydrin.

The reaction product of these epoxidation reactions may be washed with or without water under heating and reduced pressure at 110-250.
Epihalohydrin and other additional solvents are removed at a temperature of 1.3 ° C. and a pressure of 1.33 kPa or less. In order to further reduce the amount of hydrolyzable halogenated epoxy resin, the crude epoxy resin obtained after recovering epihalohydrin and the like is dissolved again in a solvent such as toluene and methyl isobutyl ketone, and the alkali epoxy resin such as sodium hydroxide and potassium hydroxide is used. An aqueous solution of a metal hydroxide may be added for further reaction to ensure ring closure. In this case, the amount of the alkali metal hydroxide used is usually 0.5 to 10 mol, preferably 1.2 to 5.0 mol, per 1 mol of the hydrolyzable chlorine remaining in the crude epoxy resin. The reaction temperature is usually 50 to 12
At 0 ° C., the reaction time is usually 0.5 to 3 hours. For the purpose of improving the reaction rate, a phase transfer catalyst such as a quaternary ammonium salt or a crown ether may be present. When the phase transfer catalyst is used, the amount of the phase transfer catalyst is as follows.
The range of 0.1 to 3.0 parts by weight relative to 00 parts by weight is preferred.

After completion of the reaction, the formed salt is removed by filtration, washing with water, and the like, and the solvent such as toluene and methyl isobutyl ketone is distilled off under reduced pressure under heating to obtain the epoxy resin of the present invention.

Hereinafter, the epoxy resin composition of the present invention will be described. The epoxy resin of the present invention can be used alone or in combination with another epoxy resin. When used in combination, the proportion of the epoxy resin of the present invention in the total epoxy resin is preferably 30% by weight or more, particularly 40% by weight.
The above is preferred.

As other epoxy resins that can be used in combination with the epoxy resin used in the present invention, all known and commonly used epoxy resins can be used. For example, bisphenol A epoxy resin and bisphenol F epoxy resin are exemplified. Phenol novolak type epoxy resin, cresol novolak type epoxy resin, biphenyl type epoxy resin, triphenylmethane type epoxy resin, dicyclopentadiene phenol addition reaction type epoxy resin, and the like, but are not limited thereto. These epoxy resins may be used alone or in combination of two or more.

As the curing agent used in the epoxy resin composition of the present invention, all known and commonly used curing agents such as amine compounds, acid anhydride compounds, amide compounds and phenol compounds are used. be able to. For example, diaminodiphenylmethane, diethylenetriamine, triethylenetetramine, diaminodiphenylsulfone, isophoronediamine, dicyandiamide, a polyamide resin synthesized from a dimer of linolenic acid and ethylenediamine, phthalic anhydride, trimellitic anhydride, pyroanhydride Mellitic acid, maleic anhydride, tetrahydrophthalic anhydride, methyltetrahydrophthalic anhydride, methylnadic anhydride, hexahydrophthalic anhydride, methylhexahydrophthalic anhydride, phenol-novolak, dicyclopentadiene phenol addition resin, phenol aralkyl resin polyhydric phenols and their modified products, including such, imidazo - Le, BF ₃ - amine complex, but such guanidine derivatives are not limited thereto These may be used alone or in combination of two or more.

In the epoxy resin composition of the present invention, the amount of the curing agent used is such that the amount of active hydrogen groups in the curing agent is 0.7 with respect to one equivalent of the epoxy group of the epoxy resin, since good curing properties can be obtained. An amount that results in 〜1.5 equivalents is preferred. Further, the epoxy resin composition of the present invention may contain various additives such as fillers such as silica, alumina and talc, silane coupling agents, release agents and pigments, if necessary.

The epoxy resin composition of the present invention can be obtained by uniformly mixing the components. The epoxy resin composition of the present invention containing the epoxy resin of the present invention, the curing agent and, if necessary, a curing accelerator can be easily formed into a cured product by a method similar to a conventionally known method. For example, if necessary, an epoxy resin and a compounding agent such as a curing agent and a filler are sufficiently mixed using an extruder, a kneader, a roll, or the like until a uniform mixture is obtained to obtain an epoxy resin composition. After the epoxy resin composition is melted, molded using a casting or transfer molding machine or the like, and further heated at 80 to 200 ° C. for 2 to 10 hours, a cured product can be obtained. Further, the epoxy resin composition of the present invention, toluene, xylene,
It can be dissolved in a solvent such as acetone, methyl ethyl ketone, methyl isobutyl ketone or the like to form a varnish and used as a coating. Further, a prepreg obtained by impregnating a base material such as glass fiber, carbon fiber, polyester fiber, polyamide fiber, alumina fiber, paper or the like with the varnish and drying by heating may be subjected to hot press molding to obtain a cured product. The solvent used in this case is usually 10 to 80% by weight, preferably 1% by weight in the mixture of the epoxy resin composition of the present invention and the solvent.
An amount occupying 5 to 75% by weight, particularly preferably 15 to 65% by weight, is used.

[0070]

EXAMPLES The present invention will be described below in more detail with reference to Examples and Comparative Examples. In the following, parts and percentages are by weight unless otherwise specified.

Synthesis Example 1 A flask equipped with a thermometer, a dropping funnel, a cooling pipe, a fractionating pipe, and a stirrer was charged with 185 parts (0.81 parts) of bisphenol A.
Mol), α, α'-paraxylene dichloride 87.5
Parts (0.5 mol), 500 parts of methyl isobutyl ketone,
3 parts of tetraethylammonium chloride were charged and stirred at room temperature while blowing nitrogen. 20% at 80 ° C
210 parts (1.05 mol) of aqueous sodium hydroxide
It was added over time. After completion of the addition, the mixture was further stirred at 80 ° C. for 3 hours. After completion of the reaction, the aqueous layer was discarded after adding 20 parts of first sodium phosphate to neutralize. Further, the organic layer was washed with water three times with 100 parts of water, and then methyl isobutyl ketone was removed by heating under reduced pressure to obtain 230 parts of a compound (A-1) which is a kind of the compound represented by the formula (1). Was. The hydroxyl equivalent of the obtained compound (A-1) was 386 g /.
Was equivalent.

Then, 193 parts of the compound (A-1) obtained by the above reaction (0.5 equivalent of hydroxyl group) and 463 parts of epichlorohydrin (5 parts) were applied to a flask equipped with a thermometer, a condenser and a stirrer while purging with nitrogen gas. .0 mol), n
-53 parts of butanol were charged and dissolved. After the temperature was raised to 50 ° C., 110 parts (0.55 mol) of a 20% aqueous sodium hydroxide solution was added over 3 hours, and then a further 5 parts were added.
The reaction was performed at 0 ° C. for 1 hour. After completion of the reaction, unreacted epichlorohydrin was distilled off under reduced pressure at 150 ° C. 300 parts of methyl isobutyl ketone and 50 parts of n-butanol were added to the crude epoxy resin thus obtained and dissolved. Further, 15 parts of a 10% aqueous sodium hydroxide solution was added to this solution, and
After the reaction at 2 ° C. for 2 hours, washing with 100 parts of water was repeated three times until the pH of the washing solution became neutral. Next, the inside of the system was dehydrated by azeotropic distillation, and after passing through microfiltration, the solvent was distilled off under reduced pressure to obtain 206 parts of the target epoxy resin (A-2). The epoxy equivalent of the obtained epoxy resin was 468 g / equivalent.

SYNTHESIS EXAMPLE 2 Formula (1) was obtained in the same manner as in Synthesis Example 1 except that bisphenol A was changed to 140 parts (0.75 mol) of biphenol.
Compound (B-1) 191 which is a kind of the compound represented by the formula:
Got a part. The hydroxyl equivalent of the obtained compound (B-1) is 3
82 grams / equivalent. Next, compound (A-1)
Was changed to 191 parts (0.5 equivalents of hydroxyl group) of Compound (B-1) to obtain 205 parts of a target epoxy resin (B-2) in the same manner as in Synthesis Example 1. The epoxy equivalent of the obtained epoxy resin was 469 g / equivalent.

Synthesis Example 3 Synthesis was carried out except that bisphenol A was changed to 322 parts (2.0 equivalents of hydroxyl group) of dicyclopentadiene-phenol polyadduct (phenol dinuclear content: 86% by weight, hydroxyl equivalent: 162 g / equivalent). In the same manner as in Example 1, the formula (1)
Compound (C-1) 366 which is a kind of the compound represented by the formula:
Got a part. The hydroxyl equivalent of the obtained compound (B-1) is 3
77 grams / equivalent. Next, compound (A-1)
Was changed to 189 parts of intermediate (C-1) (0.5 equivalents of hydroxyl group) to obtain 201 parts of target epoxy resin (C-2) in the same manner as in Synthesis Example 1. The epoxy equivalent of the obtained epoxy resin was 468 g / equivalent.

Synthesis Example 4 The same procedure as in Synthesis Example 1 was repeated except that bisphenol A was changed to 436 parts (2.28 equivalents of hydroxyl group) of a fluorene-bisphenol compound represented by the chemical formula (16).
Compound (D-1) 453, which is a kind of the compound represented by
Got a part. The hydroxyl equivalent of the obtained intermediate (D-1) is 3
84 grams / equivalent. Next, compound (A-1)
Was changed to 192 parts of compound (D-1) (0.5 equivalent of hydroxyl group), and 202 parts of desired epoxy resin (D-2) was obtained in the same manner as in Synthesis 1. The epoxy equivalent of the obtained epoxy resin was 470 g / equivalent.

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Examples 1-4 and Comparative Example 1 The epoxy resin obtained in Synthesis Examples 1-4 or a bisphenol A type solid epoxy resin (EPICLON 105
5: Using a phenol novolak resin (PHENOLITETD-2131: manufactured by Dainippon Ink and Chemicals, softening point 80 ° C, hydroxyl equivalent 104g / equivalent) as a curing agent using Dainippon Ink and Chemicals, epoxy equivalent 470g / equivalent. Using triphenylphosphine (TPP) as a curing accelerator, the composition shown in Table 1 was blended, and the mixture was melt-kneaded using two rolls at 100 ° C. for 5 minutes to obtain an epoxy resin composition. . This was press-formed at 180 ° C. for 10 minutes, and further cured at 180 ° C. for 5 hours to obtain a cured product, which was cut into a predetermined size to prepare a test piece. The storage stability of the obtained composition and the moisture absorption and dielectric constant of the test piece were measured under the following measurement conditions. Table 1 shows the evaluation results.

Storage stability: The gel time (175 ° C.) before and after standing at 30 ° C. × 72 hours was measured, and the rate of change (gel time after standing / gel time before standing) was determined.

Moisture Absorption Rate: A test piece of 75 × 25 × 2.5 (mm) was left for 300 hours under the conditions of 85 ° C. and 85% RH to determine the moisture absorption rate from the weight increase rate.

Dielectric constant: The dielectric constant of a test piece of 50 × 50 × 2.5 (mm) was measured at 25 ° C. at 1 MHz.

[0080]

[Table 1]

[0081]

Industrial Applicability The epoxy resin composition of the present invention can provide a composition having excellent storage stability and a cured product having excellent moisture resistance and electric properties, and can be used as a semiconductor sealing material. It is extremely useful for a wide range of applications such as molding materials, laminated materials such as printed wiring boards, casting materials, powder coatings and general coatings, adhesives and resist inks.

Claims (6)

[Claims] (1) Formula (1) (In the formula, n represents an average value and takes a value of 0 <n ≦ 10. A
Is a phenylene group, a divalent biphenylene group, an alkylenediphenyl group, a benzophenone residue, an oxydiphenyl group, a divalent naphthalene group, an alkylenedinaphthyl group, a binaphthyl group, or a diphenylsulfone residue;
In the valent hydrocarbon group, R represents a hydrogen atom, a halogen atom, an alkyl group having 1 to 8 carbon atoms, or an aryl group, and each R may be the same or different. An epoxy resin composition comprising, as essential components, an epoxy resin having a structure obtained by reacting the compound represented by the formula (1) with epihalohydrin, and a curing agent. 2. A in the formula (1) is represented by the formula (2). (Wherein, X represents a hydrocarbon group having 1 to 14 carbon atoms, a carbonyl group, a sulfone group, or a direct bond; R represents a hydrogen atom, a halogen atom, an alkyl group having 1 to 8 carbon atoms, or an aryl group; Each R may be the same or different from each other.), Formula (3) (In the formula, R represents a hydrogen atom, a halogen atom, an alkyl group having 1 to 8 carbon atoms, or an aryl group, and each R may be the same or different from each other.) 4] Or the formula (5) The epoxy resin composition according to claim 1, which has a skeleton represented by: 3. The epoxy resin composition according to claim 1, wherein B in the formula (1) is a methylene group. 4. X in the formula (2) is represented by the formula (6). Or formula (7): The epoxy resin composition according to claim 1, 2 or 3, which has a skeleton represented by: 5. The epoxy resin according to claim 1, wherein the epoxy equivalent of the epoxy resin obtained by reacting the compound represented by the formula (1) with epihalohydrin is in the range of 250 to 600 g / equivalent. The epoxy resin composition according to claim 1. 6. A cured product obtained by curing the epoxy resin composition according to any one of claims 1 to 5.