JP2000204141A - Polyhydric hydroxy resin, epoxy resin, epoxy resin composition including them and its cured product - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide an epoxy resin and a polyhydric hydroxy resin which have performance excellent in wet endurance, heat resistance and mechanical characteristics and useful in uses such as lamination, molding, casting and adhesion, and also to provide an epoxy resin composition and its cured product both using the same resins. SOLUTION: This polyhydric hydroxy resin is obtained by reacting both 1.5-20 mol condensing agent of the formula (wherein, each of Rs is independently H or a 1-6C hydrocarbon group) and 4-40 mol phenol with 1 mol condensed polycyclic aromatic hydrocarbon having two or more aromatic rings in the presence of an acid catalyst. This epoxy resin is obtained by reacting the polyhydric hydroxy resin with epichlorohydrin. This epoxy resin composition includes at least one selected from the group consisting of the epoxy resin and the polyhydric hydroxy resin. This cured product is obtained by curing the epoxy resin composition.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

TECHNICAL FIELD The present invention relates to an epoxy resin which gives a cured product having excellent mechanical strength such as moisture resistance, heat resistance and impact resistance, and a useful epoxy resin raw material or epoxy resin curing agent. The present invention relates to a multivalent hydroxy resin, and further relates to an epoxy resin composition and a cured product thereof using the same, which are suitably used for semiconductor encapsulation, laminates, coating materials, composite materials, and the like.

[0002]

2. Description of the Related Art In recent years, development of higher performance base resins has been demanded, especially with the progress of advanced materials.
For example, in the field of semiconductor encapsulation, the problem of package cracking has become more serious due to the recent trend toward thinner packages, larger areas, and the spread of surface mounting methods for high-density packaging. As the base resin of
Improvements in moisture resistance, heat resistance, impact resistance and the like are strongly demanded. Further, epoxy resins as composite matrix resins used in the aerospace industry are required to have even higher heat resistance and moisture resistance.

[0003] However, there is no known epoxy resin that satisfies these requirements. For example, a well-known bisphenol-type epoxy resin is liquid at room temperature, is excellent in workability, and is widely used because it is easy to mix with a curing agent and an additive. There is a problem in terms of moisture resistance. A phenol novolak type epoxy resin is known as having improved heat resistance, but has problems in moisture resistance and impact resistance.

Therefore, for example, Japanese Patent Application Laid-Open No. 63-23812
No. 2 proposes an epoxy compound of a phenol aralkyl resin for the purpose of improving moisture resistance and impact resistance, but this is not sufficient in terms of heat resistance. JP-A-64-79215 and the like propose an epoxy compound of a dihydric phenol aralkyl resin for the purpose of high heat resistance, but this is not sufficient in terms of moisture resistance.

[0005]

The inventors of the present invention have conducted intensive studies in view of the above-mentioned problems, and as a result, have found that a polyvalent hydroxy resin or epoxy resin having a specific polycyclic aromatic structure can be used. The inventors have found that the above problems can be overcome, and have reached the present invention.

Accordingly, an object of the present invention is to provide a material having excellent properties such as excellent moisture resistance and heat resistance and excellent mechanical properties such as impact resistance, and is useful for applications such as lamination, molding, casting, and adhesion. Another object of the present invention is to provide a novel epoxy resin, a polyvalent hydroxy resin useful as an epoxy resin raw material or an epoxy resin curing agent, an epoxy resin composition using the same, and a cured product thereof.

[0007]

That is, the present invention provides a method of
The following general formula (1) is based on 1 mol of the condensed polycyclic aromatic hydrocarbon having at least one aromatic ring.

[0008]

Embedded image

(Wherein, R independently represents a hydrogen atom or a hydrocarbon group having 1 to 6 carbon atoms) 1.5 to 20 mol of a condensing agent and 4 to 40 mol of phenols are represented by the following formula: It is a novel polyvalent hydroxy resin obtained by reacting in the presence of a catalyst.

[0010] The present invention is also a novel epoxy resin obtained by reacting the above polyvalent hydroxy resin with epichlorohydrin. Furthermore, the present invention is an epoxy resin composition comprising an epoxy resin and a curing agent, wherein the epoxy resin composition comprises at least one of the epoxy resin and the polyvalent hydroxy resin as an essential component, A cured product obtained by curing the epoxy resin composition.

Hereinafter, the present invention will be described in detail. The polyvalent hydroxy resin of the present invention has the general formula (1) based on 1 mol of a condensed polycyclic aromatic hydrocarbon having two or more aromatic rings.
1.5 to 20 mol of a condensing agent represented by
It is obtained by reacting 40 moles in the presence of an acidic catalyst.

The fused polycyclic aromatic hydrocarbon having two or more aromatic rings includes, for example, naphthalene, methylnaphthalenes, ethylnaphthalenes, isopropylnaphthalenes, dimethylnaphthalenes, diethylnaphthalenes, diisopropylnaphthalene , Acenaphthene, acenaphthylene, fluorene, terphenyls, phenanthrene, anthracene, pyrene, fluoranthene, etc. From the viewpoints of moisture resistance and heat resistance, acenaphthene, acenaphthylene, phenanthrene, anthracene and pyrene are particularly preferred.

The condensed polycyclic aromatic hydrocarbon includes
A mixture of the above compounds may be used, and the mixture may further contain a polycyclic aromatic hydrocarbon other than a condensed system such as diphenyl ether and dibenzofuran, and a polycyclic aromatic compound other than a hydrocarbon.

Further, the condensing agent used in the present invention includes:
Xylylene glycols represented by the above general formula (1) are used. As the isomer of xylylene glycols, any of a p-form, an m-form and an o-form may be used, but from the viewpoint of the reactivity when synthesizing a polyvalent hydroxy resin and the heat resistance when a cured product is obtained. The p-form is preferred. Examples of the xylylene glycol represented by the general formula (1) include, for example, p-xylylene glycol, α, α′-dimethoxy-
p-xylene, α, α′-diethoxy-p-xylene, α,
α′-diisopropoxy-p-xylene, α, α′-dibutoxy-p-xylene, m-xylylene glycol, α, α′-dimethoxy-m-xylene, α, α′-diethoxy-m-xylene, α, α'-diisopropoxy-m-xylene, α, α'-
Dibutoxy-m-xylene, o-xylylene glycol,
α, α′-Dimethoxy-o-xylene, α, α′-diethoxy-o-xylene, α, α′-diisopropoxy-o-xylene, α, α′-dibutoxy-o-xylene and the like.

The amount of the condensing agent used is 1.5 to 20 mol, preferably 2 to 1 mol per mol of the condensed polycyclic aromatic hydrocarbon.
The range is from 10 to 10 mol. When the amount of the condensing agent used is less than 1.5 mol per 1 mol of the condensed polycyclic aromatic hydrocarbon, the molecular weight of the obtained polyvalent hydroxy resin increases and the viscosity also increases, and the epoxy resin composition As the moldability decreases, and when it is more than 2.0 mol, the amount of the condensed polycyclic aromatic hydrocarbon in the obtained polyvalent hydroxy resin decreases, and the heat resistance and the moisture resistance decrease, which is preferable. Absent. The amount of the condensing agent used is preferably smaller than the total number of moles of the condensed polycyclic aromatic hydrocarbon and the phenol in order not to leave the hydroxymethyl group or alkoxymethyl group in the unreacted condensing agent. In addition, when the hydroxymethyl group or the alkoxymethyl group remains, the moisture resistance of the cured product decreases.

Next, the phenols used in the present invention include alkyl-substituted or unsubstituted alkyl groups having 1 to 6 carbon atoms.
Monovalent, divalent or trivalent phenols or naphthols are used. Specifically, phenol, o-cresol, m-cresol, p-cresol, ethylphenols, isopropylphenols, tertiary butylphenols, phenyl Phenols, 2,6-xylenol, 2,6-diethylphenol, hydroquinone, resorcin, catechol, pyrogallol, phloroglucinol, 1-naphthol, 2-naphthol, 1,5-naphthalenediol, 1,6-naphthalenediol, 1,7-naphthalene diol, 2,6-naphthalene diol, 2,7-naphthalene diol, 1,3,6-trihydroxynaphthalene, 1,3,7-trihydroxynaphthalene, 2,3,6-trihydroxynaphthalene And the like.
These phenols or naphthols may be used alone or in combination of two or more.

The amount of the phenol used is 4 to 40 mol, preferably 6 to 20 mol, per 1 mol of the condensed polycyclic aromatic hydrocarbon. When the amount of the phenol used is less than 4 moles per 1 mole of the condensed polycyclic aromatic hydrocarbon, the molecular weight of the obtained polyhydric hydroxy resin increases and the viscosity also increases, resulting in an epoxy resin composition. When the amount of the phenols is less than 40 mol, the amount of unreacted phenols increases, which is not industrially preferable.

When the condensed polycyclic aromatic hydrocarbon, the condensing agent and the phenol are reacted, the order of the reaction of each component is not particularly limited, but usually, a method of simultaneously reacting these three components. Is used. In some cases, for example, when the reactivity of the condensed polycyclic aromatic hydrocarbon is low, the condensed polycyclic aromatic hydrocarbon is efficiently reacted, and the condensed polycyclic aromatic hydrocarbon is contained in the structure of the obtained polyhydroxy resin. For the purpose of effectively introducing a cyclic aromatic hydrocarbon, a method of reacting a condensed polycyclic aromatic hydrocarbon with a condensing agent in advance and then reacting a phenol may be applied.

This reaction is preferably performed in the presence of an acidic catalyst, and the acidic catalyst can be appropriately selected from well-known inorganic acids and organic acids. Examples of such acidic catalysts include mineral acids such as hydrochloric acid, sulfuric acid, and phosphoric acid, and organic acids such as formic acid, oxalic acid, trifluoroacetic acid, and p-toluenesulfonic acid, zinc chloride, aluminum chloride, and iron chloride. Examples thereof include Lewis acids such as boron trifluoride, and solid acids such as activated clay, silica-alumina, and zeolite. The amount of the acidic catalyst used is usually 0.1 to 10% by weight, preferably 0.2 to 5% by weight. If the amount of the acidic catalyst is less than 0.1% by weight, the reaction time becomes longer,
On the other hand, if it is more than 10% by weight, the load of acid removal by washing with water or the like increases, which is not preferable.

The fused polycyclic aromatic hydrocarbon according to the present invention,
The reaction between the condensing agent and the phenol is usually 10 to 250
C. for 1-20 hours. Further, alcohols such as methanol, ethanol, propanol, butanol, ethylene glycol, methyl cellosolve and ethyl cellosolve, benzene, toluene, chlorobenzene, dichlorobenzene and the like can be used as a reaction solvent.

After completion of the above reaction, if necessary, neutralization,
The catalyst is removed by a method such as washing with water, and if necessary, the remaining solvent and unreacted phenol compound are removed from the system by a method such as distillation under reduced pressure to obtain a polyvalent hydroxy resin. The amount of the unreacted phenol compound is usually 3% by weight or less, preferably 1% by weight or less of the obtained polyvalent hydroxy resin. When the amount of the unreacted phenol compound is more than 3% by weight of the obtained polyvalent hydroxy resin, the heat resistance of the cured product decreases.

Next, the epoxy resin of the present invention is obtained by reacting the above-mentioned polyvalent hydroxy resin with epichlorohydrin. This reaction can be performed in the same manner as a usual epoxidation reaction.

For example, after dissolving the above polyhydric hydroxy resin in excess epichlorohydrin, sodium hydroxide,
In the presence of an alkali metal hydroxide such as potassium hydroxide,
A method in which the reaction is carried out at 50 to 150 ° C, preferably 60 to 120 ° C for 1 to 10 hours, may be mentioned. The amount of the alkali metal hydroxide used at this time is in the range of 0.8 to 2 mol, preferably 0.9 to 1.2 mol, per 1 mol of the hydroxyl group in the polyvalent hydroxy resin.

Epichlorohydrin is used in excess with respect to the hydroxyl groups in the polyhydric hydroxy resin, but is usually used in an amount of 1.0 to 1 mol of the hydroxyl groups in the polyhydric hydroxy resin.
The range is 5 to 15 moles, preferably 2 to 8 moles. After the completion of the reaction, excess epichlorohydrin is distilled off, and the obtained residue is dissolved in a solvent such as toluene or methyl isobutyl ketone, which is filtered and washed with water to remove inorganic salts, and then the solvent is distilled off. Thereby, the desired epoxy resin can be obtained.

Further, the epoxy resin composition of the present invention comprises an epoxy resin and a curing agent. At least one of the novel epoxy resin of the present invention as an epoxy resin component and the novel polyvalent hydroxy resin of the present invention as a curing agent component. One of them is blended as an essential component.

In the epoxy resin composition of the present invention, when the novel epoxy resin of the present invention is an essential component as an epoxy resin component, any curing agent generally known as a curing agent for epoxy resins can be used. .
For example, dicyandiamide, polyhydric phenols, acid anhydrides, aromatic and aliphatic amines and the like can be used. Specific examples of polyhydric phenols include, for example, bisphenol A, bisphenol F, bisphenol S , Fluorene bisphenol, 4,4'-biphenol,
2,2'-biphenol, hydroquinone, resorcinol, divalent phenols such as naphthalene diol, or
Trivalent or higher phenol represented by tris- (4-hydroxyphenyl) methane, 1,1,2,2-tetrakis (4-hydroxyphenyl) ethane, phenol novolak, o-cresol novolak, naphthol novolak, polyvinylphenol, etc. Phenols, naphthols or divalent phenols such as bisphenol A, bisphenol F, bisphenol S, fluorene bisphenol, 4,4′-biphenol, 2,2′-biphenol, hydroquinone, resorcinol, naphthalene diol and the like Formaldehyde, acetaldehyde, benzaldehyde,
Examples include polyhydric phenolic compounds synthesized with a condensing agent such as p-hydroxybenzaldehyde and p-xylylene glycol.The acid anhydrides include phthalic anhydride, tetrahydrophthalic anhydride, and methyltetrahydrophthalic anhydride. , Hexahydrophthalic anhydride, methylhexahydrophthalic anhydride, methylhymic anhydride, nadic anhydride, trimellitic anhydride and the like. Also,
As amines, 4,4′-diaminodiphenylmethane,
4,4'-diaminodiphenylpropane, 4,4'-diaminodiphenylsulfone, m-phenylenediamine, aromatic amines such as p-xylylenediamine, ethylenediamine,
Examples thereof include aliphatic amines such as hexamethylenediamine, diethylenetriamine, and triethylenetetramine.
Further, the novel polyvalent hydroxy resin of the present invention can be used as a curing agent. These curing agents can be used alone or in combination of two or more. The compounding amount of the epoxy resin according to the present invention is 5 to 10 in the entire epoxy resin for the purpose of expressing the functions of moisture resistance and heat resistance, which are the objects of the present invention.
The content is preferably in the range of 0% by weight. When the novel epoxy resin of the present invention is used as an essential component as the epoxy resin component, another epoxy resin may be mixed with the novel epoxy resin of the present invention.

On the other hand, when the novel polyvalent hydroxy resin of the present invention is used as a curing agent in the epoxy resin composition of the present invention as an essential component, the epoxy resin may be an ordinary epoxy resin having two or more epoxy groups in the molecule. All resins can be used. As such an epoxy resin, for example,
Bivalent phenols such as bisphenol A, bisphenol S, fluorene bisphenol, 4,4′-biphenol, 2,2′-biphenol, hydroquinone, resorcin, or tris- (4-hydroxyphenyl) methane, 1,1, Trivalent or higher phenols such as 2,2-tetrakis (4-hydroxyphenyl) ethane, phenol novolak and o-cresol novolac, or glycidyl ether compounds derived from halogenated bisphenols such as tetrabromobisphenol A Is mentioned. Alternatively, the novel epoxy resin of the present invention obtained from the polyvalent hydroxy resin obtained by using the condensing agent represented by the general formula (1) can be used. These epoxy resins can be used alone or in combination of two or more.

The compounding amount of the novel polyhydric hydroxy resin according to the present invention is preferably in the range of 5 to 100% by weight based on the whole epoxy resin in order to achieve the functions of moisture resistance and heat resistance which are the object of the present invention. Good. When the novel polyvalent hydroxy resin of the present invention is used as a curing agent as an essential component, another curing agent may be mixed with the novel polyvalent hydroxy resin of the present invention.

Also, the novel epoxy resin of the present invention, or
In the epoxy resin composition of the present invention containing the novel polyvalent hydroxy resin of the present invention as an essential component, oligomers such as polyesters, polyamides, polyimides, polyethers, polyurethanes, petroleum resins, indene maron resins, phenoxy resins and the like are included. A molecular compound may be appropriately compounded, or additives such as an inorganic filler, a pigment, a flame retardant, a thixotropic agent, a coupling agent, and a fluidity improver may be compounded.

Examples of the inorganic filler include spherical or crushed fused silica, silica powder such as crystalline silica, alumina powder, glass powder, mica, talc, calcium carbonate, alumina, hydrated alumina and the like. Examples of the pigment include an organic or inorganic extender, a scale pigment, and the like. Examples of the thixotropic agent include silicone type, castor oil type, aliphatic amide wax, oxidized polyethylene wax, and organic bentonite type, and examples of the fluidity improver include phenyl glycidyl ether and naphthyl glycidyl ether. be able to. Further, if necessary, conventionally known curing accelerators such as amines, imidazoles, organic phosphines, Lewis acids and the like can be used.

The amount of these additives is usually
It is in the range of 0.2 to 5 parts by weight based on 100 parts by weight of the epoxy resin. Further, if necessary, the epoxy resin composition of the present invention may contain a releasing agent such as carnauba wax and OP wax, a coupling agent such as γ-glycidoxypropyltrimethoxysilane, and a coloring agent such as carbon black. And flame retardants such as antimony trioxide, low stress agents such as silicone oil, and lubricants such as calcium stearate.

The cured product of the present invention can be obtained by molding the above epoxy resin composition by a method such as casting, compression molding, transfer molding and the like. The temperature at the time of formation is usually in the range of 120 to 220 ° C.

[0033]

The present invention will be specifically described below based on examples and comparative examples.

Example 1 (Production of polyvalent hydroxy resin) 61.6 g of acenaphthene was placed in a 2-liter four-necked flask.
(0.4 mol), α, α′-dimethoxy-p-xylene 26
5.6 g (1.6 mol) and 752 g of phenol
(8.0 mol) and heated and dissolved at 60 ° C. under a nitrogen stream. Thereafter, 10 g of p-toluenesulfonic acid was gradually added. After completion of the dropwise addition, the reaction was carried out at 160 ° C. for 2 hours with stirring. After the reaction, the mixture was neutralized with sodium carbonate, and excess phenol was distilled off under reduced pressure to obtain 436 g of a brown resin. The softening point of the obtained resin was 50 ° C., the melt viscosity at 150 ° C. based on the ICI cone plate method was 0.3 poise, and the hydroxyl equivalent was 179. GP of the obtained resin
The C chart is shown in FIG. 1, and the FD-MS spectrum is shown in FIG.

Here, the GPC measurement was carried out using an apparatus: HLC-82.
A [manufactured by Tosoh Corporation] and column: TSK-GEL20
Using 00 × 3 pieces and TSK-GEL 4000 × 1 piece (all manufactured by Tosoh Corporation), solvent: tetrahydrofuran,
Flow rate: 1.0 ml / min, temperature: 38 ° C., detector: RI

Example 2 (Preparation of polyhydric hydroxy resin) 80.8 g of pyrene (0.4
Mol), 265.6 g of α, α'-dimethoxy-p-xylene
(1.6 mol) and heated to 60 ° C. under a nitrogen stream. Thereafter, 18 g of p-toluenesulfonic acid was added as a catalyst. After completion of the addition, the mixture was reacted for 1 hour while stirring at 160 ° C., and 25.6 g of produced methanol was recovered. Thereafter, 752 g (8.0 mol) of phenol was added, and the mixture was further reacted at 160 ° C. for 4 hours. After the reaction, the mixture was neutralized with sodium carbonate, and excess phenol was distilled off under reduced pressure to obtain 380 g of a brown resin. The obtained resin has a softening point of 78 ° C.
The melt viscosity at 150 ° C. based on the ICI cone plate method was 4.2 poise, and the hydroxyl equivalent was 232. FIG. 3 shows a GPC chart of the obtained resin, and FIG. 4 shows an FD-MS spectrum.

Example 3 (Production of polyhydroxy resin) 178 g of anthracene was placed in a 2-liter 4-neck flask.
(1.0 mol), α, α′-dimethoxy-p-xylene 66
4 g (4.0 mol) was charged and heated to 60 ° C. under a nitrogen stream. Then, p-toluenesulfonic acid 3 was used as a catalyst.
3.5 g were added. After completion of the addition, the reaction was carried out for 1 hour while stirring at 160 ° C., and 72 g of produced methanol was recovered. Thereafter, 864 g (8.0 mol) of o-cresol was added, and the mixture was further reacted at 160 ° C. for 3 hours. After the reaction, the mixture was neutralized with sodium carbonate, and excess o-cresol was distilled off under reduced pressure to obtain 1020 g of a brown resin. The softening point of the obtained resin is 84 ° C. and 150 based on the ICI cone plate method.
The melt viscosity at ° C was 4.4 poise, and the hydroxyl equivalent was 247. FIG. 5 shows a GPC chart of the obtained resin, and FIG. 6 shows an FD-MS spectrum.

Example 4 (Production of Epoxy Resin) 160 g of the resin obtained in Example 2 was dissolved in 640 g of epichlorohydrin, and the solution was dissolved under reduced pressure (about 140 mmHg) under 65
At 48 ° C., 56.2 g of a 48% aqueous sodium hydroxide solution was added.
It was added dropwise over 0 hours. During this time, generated water was removed from the system by azeotropic distillation with epichlorohydrin, and the distilled epichlorohydrin was returned to the system. After the completion of the dropwise addition, the reaction was continued for another 30 minutes. Thereafter, epichlorohydrin was distilled off to obtain a crude epoxy resin. After dissolving the obtained crude epoxy resin in 400 ml of methyl isobutyl ketone,
The salt generated by washing with water was removed, the mixture was heated to 80 ° C., and 36 g of 10% sodium hydroxide was added thereto with stirring, and the mixture was reacted for 2 hours. After the reaction, after washing with deionized water,
Methyl isobutyl ketone was distilled off to obtain 162 g of a brown liquid epoxy resin. The epoxy equivalent is 304 and I
The melt viscosity at 150 ° C. based on the CI cone plate method was 1.6 poise or less, and the hydrolyzable chlorine was 410 ppm. FIG. 7 shows a GPC chart of the obtained resin.

The hydrolyzable chlorine was obtained by dissolving 0.5 g of a resin sample in 30 ml of 1,4-dioxane and boiling under reflux for 30 minutes in 5 ml of a 1N-KOH / methanol solution, followed by silver nitrate solution. It was determined by performing a potentiometric titration.

Example 5 (Production of Epoxy Resin) Using 160 g of the resin obtained in Example 3, 960 g of epichlorohydrin and 53 g of a 48% aqueous sodium hydroxide solution, the reaction was carried out in the same manner as in Example 4, and the brown epoxy resin 1
69.6 g were obtained. Epoxy equivalent was 324, softening point was 61 ° C., melt viscosity at 150 ° C. was 3.4 poise, and hydrolyzable chlorine was 570 ppm. FIG. 8 shows a GPC chart of the obtained resin.

Examples 6 to 10 and Comparative Examples 1 and 2 Resins synthesized in Examples 1, 4 and 5 were obtained by using o-
Cresol novolak type epoxy resin (ECN), phenol novolak (PN) having a softening point of 68 ° C and softening point of 6
8 ° C. phenol aralkyl resin [XL-225-3
L: Mitsui Toatsu (PA)], triphenylphosphine as a curing accelerator, and γ as a silane coupling agent.
-Glycidoxypropyltrimethoxysilane was used to form a resin composition with the composition shown in Table 1, and then molded (150 ° C,
3 minutes) to obtain a cured test piece.

The test pieces were post-cured at 180 ° C. for 12 hours and then subjected to various physical property tests. Table 2 shows the results. The glass transition point and the coefficient of linear expansion were measured at a heating rate of 7 ° C./min using a thermomechanical measuring device. The water absorption is measured when a disk having a diameter of 50 mm and a thickness of 3 mm is formed using the epoxy resin composition, post-cured, and allowed to absorb moisture at 85 ° C. and 85% RH for a predetermined time. Yes, the crack occurrence rate is QFP-80 pi
n (14 × 20 × 2.5 mmt) was molded, post-cured, absorbed in moisture for a predetermined time under the same conditions as the water absorption, immersed in a solder bath at 260 ° C. for 10 seconds, and observed and determined for the state of the package. Was.

[0043]

[Table 1]

[0044]

[Table 2]

[0045]

The cured product obtained by curing the epoxy resin composition using the epoxy resin and the polyvalent hydroxy resin of the present invention has excellent moisture resistance, heat resistance, and mechanical properties such as impact resistance. It has excellent performance and can be suitably used for applications such as lamination, molding, casting, and adhesion.

[Brief description of the drawings]

FIG. 1 is a diagram showing G of the resin obtained in Example 1.
It is a figure showing a PC chart.

FIG. 2 is a graph showing the F value of the resin obtained in Example 1.
It is a figure which shows a D-MS spectrum.

FIG. 3 is a graph showing the G of the resin obtained in Example 2.
It is a figure showing a PC chart.

FIG. 4 is a graph showing the F value of the resin obtained in Example 2.
It is a figure which shows a D-MS spectrum.

FIG. 5 shows G of the resin obtained in Example 3.
It is a figure showing a PC chart.

FIG. 6 is a graph showing F of the resin obtained in Example 3.
It is a figure which shows a D-MS spectrum.

FIG. 7 is a graph showing G of the resin obtained in Example 4.
It is a figure showing a PC chart.

FIG. 8 shows G of the resin obtained in Example 5.
It is a figure showing a PC chart.

 ──────────────────────────────────────────────────続 き Continued on the front page F term (reference) 4J032 CA16 CB05 CD00 CD01 CF03 CG00 CG06 4J036 AC01 AC02 AC03 AC05 AD01 AD08 AD09 AE07 AF06 DB06 DB15 DB21 DB22 DC03 DC06 FB01 FB06 FB08 JA01 JA07 JA08

Claims (5)

[Claims] 1. A compound represented by the following general formula (1) per mole of a condensed polycyclic aromatic hydrocarbon having two or more aromatic rings. (However, in the formula, R is each independently a hydrogen atom or a carbon number 1 to
6 to 20) condensing agents represented by the following formulas:
A multivalent hydroxy resin obtained by reacting 4 to 40 mol of phenols and 4 to 40 mol of phenols in the presence of an acidic catalyst. 2. The fused polycyclic aromatic hydrocarbon comprises acenaphthene, acenaphthylene, anthracene, phenanthrene,
The polyvalent hydroxy resin according to claim 1, which is selected from pyrene. 3. An epoxy resin obtained by reacting the polyhydric hydroxy resin according to claim 1 with epichlorohydrin. 4. An epoxy resin composition comprising an epoxy resin and a curing agent, wherein at least one of the polyhydroxy resin according to claim 1 and the epoxy resin according to claim 3 is blended as an essential component. Epoxy resin composition. 5. A cured product obtained by curing the epoxy resin composition according to claim 4.