JPH11158255A - Novel polyhydroxy compound, novel epoxy resin, their production, and epoxy resin composition and cured article prepared by using them - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain an epoxy resin which is excellent in resistances to moisture and heat and in mechanical properties such as impact strength and is useful for lamination, molding, casting, adhesion or the like, a polyhydroxy compd. useful as an epoxy resin curing agent and a production process therefor, and an epoxy resin compsn. and a cured article prepared by using them. SOLUTION: This invention provides a novel polyhydroxy compd. of formula (1) and a novel epoxy resin of formula (3). In formulas (1) and (3), A is a benzene or naphthalene ring optionally substd. by a 1-6C alkyl; R is H or methyl; G is glycidyl; (n) is 0-15; and (m)is 1, 2, or 3. A process for producing a polyhydroxy resin contg. the above polyhydroxy compd. is also provided which comprises reacting 1 mol of a phenolic compd. with 0.05-0.9 mol of a crosslinker contg. at least 50% divinylnaphthalene in the presence of an acidic catalyst.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

TECHNICAL FIELD The present invention relates to moisture resistance, heat resistance,
The present invention relates to an epoxy resin that gives a cured product having excellent mechanical strength such as impact resistance, a method for producing the same, and an epoxy resin composition using the same and a cured product thereof. It is preferably used for such purposes.

[0002]

2. Description of the Related Art In recent years, particularly with the advancement of advanced materials,
There is a need for the development of higher performance base resins. 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 more widespread use of surface mounting methods corresponding to high-density packaging. As a base resin, improvements in moisture resistance, heat resistance, impact resistance, and the like are strongly required.
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 widely used because it is liquid at room temperature and has excellent workability, and is easily mixed 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.

Japanese Patent Laid-Open Publication No. Sho 63-238,122 proposes an epoxy compound of a phenol aralkyl resin for the purpose of improving moisture resistance and impact resistance. not enough. Also, Japanese Patent Application Laid-Open
Japanese Patent Application No. 79,215 proposes 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]

SUMMARY OF THE INVENTION Accordingly, an object of the present invention is to provide a laminate, a mold, a cast, and an adhesive having excellent properties such as excellent moisture resistance and heat resistance and excellent mechanical properties such as impact resistance. It is an object of the present invention to provide an epoxy resin useful for applications such as, and a polyvalent hydroxy resin useful as an epoxy resin curing agent, a method for producing the same, an epoxy resin composition using them, and a cured product thereof.

[0006]

That is, the present invention is a novel polyhydroxy compound represented by the following general formula (1).

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Further, the present invention relates to a phenolic compound and a divinylnaphthalene represented by the following general formula (2):
% Of the phenolic compound is a polyvalent hydroxy resin containing the novel polyvalent hydroxy compound described in the above general formula (1), which is obtained by reacting with a crosslinking agent containing at least 0.1% by weight of the phenolic compound. A method for producing a polyvalent hydroxy resin, comprising reacting a crosslinking agent containing 9 mol of divinylnaphthalenes in an amount of 50% or more in the presence of an acidic catalyst.

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Further, the present invention is a novel epoxy resin represented by the following general formula (3).

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In the general formulas (1), (2) and (3), A represents a benzene ring or a naphthalene ring which may be substituted by an alkyl group having 1 to 6 carbon atoms;
R represents a hydrogen atom or a methyl group, G represents a glycidyl group, n represents a number of 0 to 15, and m represents an integer of 1 to 3.

Further, the present invention is represented by the above general formula (3) obtained by reacting a polyvalent hydroxy compound represented by the above general formula (1) or a polyvalent hydroxy resin containing the same with epichlorohydrin. It is an epoxy resin containing a novel epoxy resin.

Further, the present invention provides an epoxy resin composition comprising an epoxy resin and a curing agent, wherein the epoxy resin as an epoxy resin component, the polyvalent hydroxy compound as a curing agent component, or a polyvalent hydroxy compound containing the same. An epoxy resin composition containing at least one of the resins as an essential component, and a cured product obtained by curing the epoxy resin composition.

Hereinafter, the present invention will be described in detail. The novel polyhydroxy compound represented by the general formula (1) can be obtained by reacting a phenolic compound represented by the general formula A- (OH) m with a specific crosslinking agent. In the above general formulas and general formulas (1) and (3), A represents a benzene ring or a naphthalene ring, and these rings have 1 carbon atom.
Although A may be substituted with an alkyl group of No. 6 to 6, preferably A is an unsubstituted or methyl group-substituted benzene ring or naphthalene ring. R is a hydrogen atom or a methyl group. m is an integer of 1 to 3, preferably 1 or 2. n represents the average number of repetitions, and is from 0 to 15, preferably from 0.1 to 5. Such a polyhydric hydroxy compound is obtained by reacting a phenolic compound represented by the above general formula with a crosslinking agent represented by the general formula (2).

The phenolic compound is a substituted or unsubstituted monovalent, divalent or trivalent phenol or naphthol having 1 to 6 carbon atoms, specifically, phenol, o-cresol, m-cresol, p
-Cresol, ethylphenols, isopropylphenols, tertiarybutylphenols, 2,6-
Xylenol, 2,6-diethylphenol, hydroquinone, resorcinol, catechol, pyrogallol, phloroglucinol, 1-naphthol, 2-naphthol,
1,5-naphthalene diol, 1,6-naphthalene diol, 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.

As the crosslinking agent, there are difunctional compounds such as divinylnaphthalenes and bis (hydroxymethyl) naphthalene, but divinylnaphthalenes represented by the general formula (2) are preferred. In the general formula (2), R is a hydrogen atom or a methyl group. Although divinylnaphthalenes are not particularly limited, they can be generally produced by a dehydrogenation reaction of diethylnaphthalenes and diisopropylnaphthalenes. The divinylnaphthalenes thus obtained are 1-vinylnaphthalene,
2-vinylnaphthalene, ethylvinylnaphthalenes, diethylnaphthalenes, 1-isopropenylnaphthalene,
It often contains 2-isopropenylnaphthalene, isopropylisopropenylnaphthalenes, diisopropylnaphthalenes, etc., but it is not necessary to completely separate these, and the content of divinylnaphthalenes is 50% or more.
Preferably, the concentration may be 70% or more. Therefore,
The content of a monovinyl compound such as vinylnaphthalenes, ethylvinylnaphthalenes, isopropenylnaphthalenes, and isopropylisopropenylnaphthalenes may be 50% or less. If the content of the monovinyl compound is higher than this, the crosslink density when the resin is cured is reduced, and the heat resistance may be reduced. Specific examples of divinylnaphthalenes include 1,2-divinylnaphthalene, 1,3-divinylnaphthalene, 1,4-divinylnaphthalene,
5-divinylnaphthalene, 1,6-divinylnaphthalene, 1,7-divinylnaphthalene, 1,8-divinylnaphthalene, 2,3-divinylnaphthalene, 2,6-divinylnaphthalene, 2,7-divinylnaphthalene, 1,2
-Diisopropenylnaphthalene, 1,3-diisopropenylnaphthalene, 1,4-diisopropenylnaphthalene, 1,5-diisopropenylnaphthalene, 1,6-diisopropenylnaphthalene, 1,7-diisopropenylnaphthalene 1,8-diisopropenylnaphthalene,
There are 2,3-diisopropenylnaphthalene, 2,6-diisopropenylnaphthalene, and 2,7-diisopropenylnaphthalene, which are used alone or as a mixture. Preferred isomers of divinylnaphthalenes include:
2,6-disubstituted and 2,7-disubstituted, particularly preferred isomers are 2,6-divinylnaphthalene and 2,6
-Diisopropenylnaphthalene. The higher the content of these isomers, the higher the degree of heat resistance of the cured product.

In the reaction between the phenolic compound and the crosslinking agent, an excess amount of the phenolic compound relative to the crosslinking agent is used. The amount of the crosslinking agent to be used is generally 0.05 to 0.9 mol, preferably 0.1 to 0.7 mol, of a bifunctional naphthalene compound such as divinylnaphthalene per mol of the phenolic compound. If the amount is larger than this, the softening point of the resin becomes high, which impairs the molding workability. On the other hand, if the amount is less than this, an excessive amount of the phenolic compound is removed after the completion of the reaction, which is not industrially preferable.

This reaction is preferably performed in the presence of an acid catalyst, and the acid catalyst can be appropriately selected from well-known inorganic acids and organic acids. Such acid catalysts include:
For example, mineral acids such as hydrochloric acid, sulfuric acid, and phosphoric acid; organic acids such as formic acid, oxalic acid, trifluoroacetic acid, and p-toluenesulfonic acid; and Lewis acids such as zinc chloride, aluminum chloride, iron chloride, and boron trifluoride. Or a solid acid such as activated clay, silica-alumina and zeolite.

Usually, the reaction is carried out at
Perform for 20 hours. Further, as a reaction solvent, methanol,
Alcohols such as ethanol, propanol, butanol, ethylene glycol, methyl cellosolve and ethyl cellosolve, benzene, toluene, chlorobenzene, dichlorobenzene and the like can be used.

After completion of the reaction, if necessary, the catalyst is removed by a method such as neutralization and washing with water, and if necessary, the remaining solvent and unreacted phenolic compound are removed from the system by a method such as distillation under reduced pressure. A polyvalent hydroxy compound or a polyvalent hydroxy resin containing the same. The unreacted phenolic compound is usually at most 3%, preferably at most 1%. If the amount is more than this, the heat resistance of the cured product will decrease. However, when a phenolic compound having two or more valences is used in the reaction, the phenolic compound remaining after the reaction does not have to be removed.

The present invention also includes a polyvalent hydroxy resin containing the novel polyvalent hydroxy compound of the general formula (1). For example, when a cross-linking agent containing monovinylnaphthalenes is used as a cross-linking agent to be reacted with a phenolic compound, a novel polyvalent hydroxy compound represented by the general formula (1):
It becomes a mixture with a compound in which one or more monovinylnaphthalenes are added to the aromatic ring of the novel polyvalent hydroxy compound of the general formula (1). Further, when a mixture of two or more phenolic compounds is used in the reaction, a polyhydric hydroxy compound containing two or more phenolic compounds in one molecule may be produced in some cases. It becomes a mixture with a polyvalent hydroxy compound. Even if these are mixtures, there is no problem in exerting the effects of the present invention, and they can be used as an epoxy resin curing agent, or can be used as a raw material of the novel epoxy resin of the present invention.

The novel epoxy resin of the present invention or the epoxy resin containing the same is obtained by reacting a polyvalent hydroxy compound represented by the general formula (1) or a polyvalent hydroxy resin containing the same with epichlorohydrin. . This reaction can be performed in the same manner as a usual epoxidation reaction. For example, after dissolving the polyhydric hydroxy compound represented by the general formula (1) in an excess of epichlorohydrin, in the presence of an alkali metal hydroxide such as sodium hydroxide or potassium hydroxide, preferably at 50 to 150 ° C. Is 6
A method of reacting at 0 to 120 ° C. for 1 to 10 hours is exemplified. The amount of the alkali metal hydroxide used at this time is 0.8 to 2 mol, preferably 0.9 to 1.2 mol, per 1 mol of the hydroxyl group in the polyvalent hydroxy compound. In addition, epichlorohydrin is used in excess with respect to the hydroxyl group in the polyvalent hydroxy resin, but is usually 1.5 to 15 mol, preferably 2 to 8 mol, per mol of the hydroxyl group in the polyvalent hydroxy compound. After completion of the reaction, excess epichlorohydrin is distilled off, and the residue is dissolved in a solvent such as toluene or methyl isobutyl ketone, filtered, washed with water to remove inorganic salts, and then the solvent is distilled off to remove the desired epoxy compound. A resin can be obtained. The epoxy resin has a main component represented by the general formula (3) as a main component, but naturally includes an epoxy resin in which an epoxy group is oligomerized as an ether bond.

The epoxy resin composition of the present invention comprises an epoxy resin and a curing agent, and comprises a novel epoxy resin represented by the general formula (3) or an epoxy resin containing the same as an epoxy resin component, or a curing agent component. At least one of the polyvalent hydroxy compound represented by the formula (1) and the polyvalent hydroxy resin containing the same is blended as an essential component.

In the epoxy resin composition containing the novel epoxy resin represented by the general formula (3) or the epoxy resin containing the same as an essential component, the curing agent component is generally known as a curing agent for the epoxy resin. Anything can be used. Examples of such a curing agent include dicyandiamide, polyhydric phenols, acid anhydrides, aromatic and aliphatic amines, and the like. Specifically, examples of polyhydric phenols include bisphenol A, bisphenol F, bisphenol S, fluorene bisphenol, 4,4′-biphenol, and 2,2′-
Dihydric phenols such as biphenol, hydroquinone, resorcinol, and naphthalene diol, or tris-
(4-hydroxyphenyl) methane, 1,1,2,2-
3 represented by tetrakis (4-hydroxyphenyl) ethane, phenol novolak, o-cresol novolak, naphthol novolak, polyvinylphenol, etc.
Or higher phenols, furthermore, phenols, naphthols or bisphenol A, bisphenol F, bisphenol S, fluorene bisphenol, 4,4'-
Polyhydric phenols synthesized with condensing agents such as formaldehyde, acetaldehyde, benzaldehyde, p-hydroxybenzaldehyde, and p-xylylene glycol of dihydric phenols such as biphenol, 2,2'-biphenol, hydroquinone, resorcinol, and naphthalene diol Compounds. Examples of the acid anhydrides include phthalic anhydride, tetrahydrophthalic anhydride, methyltetrahydrophthalic anhydride, hexahydrophthalic anhydride, methylhexahydrophthalic anhydride, methylhymic anhydride, nadic anhydride, trimellitic anhydride, and the like. No. Further, as the amines, 4,4′-diaminodiphenylmethane, 4,4′-diaminodiphenylpropane, 4,4′-diaminodiphenylsulfone,
aromatic amines such as m-phenylenediamine and p-xylylenediamine; aliphatic amines such as ethylenediamine, hexamethylenediamine, diethylenetriamine and triethylenetetramine; or polyhydroxy compounds represented by the general formula (1): Polyvalent hydroxy resins and the like can be mentioned. In the epoxy resin composition of the present invention, these curing agents may be used alone or in combination of two or more, but the amount of the epoxy resin according to the present invention is based on the entire epoxy resin. 5 to 100%.

In the epoxy resin composition containing a polyvalent hydroxy compound represented by the general formula (1) or a polyvalent hydroxy resin as an essential component, the epoxy resin component may be an ordinary one having two or more epoxy groups in a molecule. Any epoxy resin can be used. Specific examples include bisphenol A, bisphenol S, fluorene bisphenol, 4,4′-biphenol, 2,2′-biphenol, hydroquinone, divalent phenols such as resorcin, and tris- (4-hydroxyphenyl). Glue derived from trivalent or higher phenols such as methane, 1,1,2,2-tetrakis (4-hydroxyphenyl) ethane, phenol novolak, o-cresol novolak, or halogenated bisphenols such as tetrabromobisphenol A. Examples thereof include a sidyl ether compound and an epoxy resin represented by the general formula (3). In the epoxy resin composition of the present invention, these epoxy resins may be used alone or in combination of two or more. However, the blending amount of the polyhydroxy compound or polyhydroxy resin according to the present invention Is 5 to 100% of the entire curing agent
It is. Incidentally, the total of the epoxy resin and the polyvalent hydroxy compound and the polyvalent hydroxy resin according to the present invention is 10% or more, preferably 30% or more, based on the total of the epoxy resin and the curing agent in the epoxy resin composition of the present invention. Good to be.

Further, the epoxy resin composition of the present invention comprises:
Polyester, polyamide, polyimide, polyether, polyurethane, petroleum resin, indene maron resin,
Oligomers or polymer compounds such as phenoxy resins may be appropriately compounded, or additives such as inorganic fillers, pigments, flame retardants, thixotropic agents, coupling agents, and fluidity improvers may be compounded. . Examples of the inorganic filler include spherical or crushed fused silica, silica powder such as crystalline silica, alumina powder, glass powder, or mica, talc, calcium carbonate, alumina, hydrated alumina, and the like. And inorganic or inorganic extender pigments and scaly pigments. Examples of the thixotropic agent include silicone, castor oil, aliphatic amide wax, oxidized polyethylene wax, and organic bentonite. Further, if necessary, conventionally known curing accelerators such as amines, imidazoles, organic phosphines, Lewis acids and the like can be used. The addition amount of the curing accelerator is usually 0.2 to 100 parts by weight of the epoxy resin.
5 parts by weight.

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 carbon black. A coloring agent, a flame retardant such as antimony trioxide, a low stress agent such as silicone oil, a lubricant such as calcium stearate, and the like may be added. This epoxy resin composition is suitable for applications such as a semiconductor sealing material.

The cured product of the present invention can be formed by molding the above epoxy resin composition by a method such as casting, compression molding, or transfer molding. The molding temperature is
Usually, it is 120 to 220 ° C.

[0027]

The present invention will be specifically described below based on examples and comparative examples. Example 1 [Production of polyhydric hydroxy resin] Phenol as a phenolic compound was placed in a 2000 ml four-necked flask.
g (3.3 mol) and 4.9 g of p-toluenesulfonic acid as a catalyst were heated to 60 ° C. under a nitrogen stream. Thereafter, 46.3% of 2,7-divinylnaphthalene, 2,6
-Divinylnaphthalene 38.9%, 2-ethyl-6-vinylnaphthalene 5.2%, 2-ethyl-7-vinylnaphthalene 4.5%, 2,6-diethylnaphthalene 1.9
%, 2,7-diethylnaphthalene 1.8%, 2-vinylnaphthalene 1.0%, other crosslinking agent 2 consisting of 0.4%
A solution in which 11.2 g was dissolved in 650 ml of toluene was gradually added dropwise over 1 hour. After the completion of the dropwise addition, the reaction was carried out for 1 hour with further stirring. After the reaction, the mixture was neutralized with sodium carbonate, and excess phenol and unreacted components in the crosslinking agent were distilled off under reduced pressure to obtain 361 g of a brown resin. The obtained resin has a softening point of 93 ° C., a melt viscosity at 150 ° C. based on the ICI cone plate method of 4.2 poise, and a hydroxyl equivalent of 2
18.5. The GPC chart of the obtained resin is shown in FIG. 1, the infrared absorption spectrum is shown in FIG. 2, and the H-NMR spectrum is shown in FIG. The GPC measurement was performed using an apparatus: HLC-8.
2A (manufactured by Tosoh Corporation) and column: TSK-GEL2
Solvent: tetrahydrofuran, flow rate: 1.0 ml / min, temperature: 38 ° C., detector: R using 000 × 3 and TSK-GEL4000 × 1 (both manufactured by Tosoh Corporation)
I was performed under the conditions of I.

Example 2 [Preparation of polyhydric hydroxy resin] 480 g (3.3 mol) of 1-naphthol as a phenolic compound, toluene 6
50 g and 6.9 g of p-toluenesulfonic acid as a catalyst
And heated to 60 ° C. under a nitrogen stream. The same reaction as in Example 1 was carried out using a solution in which 211.2 g of divinylnaphthalenes as in Example 1 was dissolved in 600 ml of toluene, to obtain 478 g of a brown resin. The obtained resin had a softening point of 118 ° C., a melt viscosity at 150 ° C. based on the ICI cone plate method of 37 poise, and a hydroxyl equivalent of 246. The GPC chart of the obtained resin is shown in FIG. 4, the infrared absorption spectrum is shown in FIG. 5, and the H-NMR spectrum is shown in FIG.

Example 3 [Production of epoxy resin] 100 g of the resin obtained in Example 1 was dissolved in 500 g of epichlorohydrin, and the solution was dissolved under reduced pressure (about 15 g).
(0 mmHg), 37 g of a 48% aqueous sodium hydroxide solution was added dropwise at 70 ° C. over 3.5 hours. During this time, the 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, salts produced by filtration were removed, washed with water, and then epichlorohydrin was distilled off to obtain a crude epoxy resin. After dissolving the obtained crude epoxy resin in 450 ml of methyl isobutyl ketone, the mixture was heated to 80 ° C., 6.8 g of 30% sodium hydroxide was added with stirring, and the mixture was reacted for 2 hours. After the reaction, the product was washed with ion-exchanged water, and then methyl isobutyl ketone was distilled off to obtain 105.2 g of a dark yellow epoxy resin. The epoxy resin has an epoxy equivalent of 288, a softening point of 75 ° C., a melt viscosity at 150 ° C. based on the ICI cone-plate method of 1.4 poise, and a hydrolyzable chlorine of 200 pp.
m. The GPC chart of the epoxy resin is shown in FIG. 7, the infrared absorption spectrum is shown in FIG. 8, and the H-NMR spectrum is shown in FIG. In addition, the hydrolyzable chlorine was used for the resin sample 0.1.
A solution obtained by dissolving 5 g in 30 ml of 1,4-dioxane was boiled and refluxed with 5 ml of a 1N-KOH / methanol solution for 30 minutes, and the solution was determined by potentiometric titration with a silver nitrate solution.

Example 4 [Production of epoxy resin] 100 g of the resin obtained in Example 2,
The reaction was carried out in the same manner as in Example 3 using 450.7 g of a 48% aqueous sodium hydroxide solution.
3 g were obtained. The epoxy equivalent of this epoxy resin is 31
The softening point was 105 ° C., the melt viscosity at 150 ° C. was 18 poise, and the hydrolyzable chlorine was 250 ppm. FIG. 10 shows a GPC chart of the epoxy resin, FIG. 11 shows an infrared absorption spectrum, and FIG. 1 shows an H-NMR spectrum.
It is shown in FIG.

Examples 5 to 9 and Comparative Examples 1 to 2 Resins synthesized in Examples 1 to 4, o-cresol novolac epoxy resin (ECN) having a softening point of 75 ° C., softening point of 6
8 ° C phenol novolak (PN) and softening point 68 ° C
Phenol aralkyl resin (XL-225-3L, manufactured by Mitsui Toatsu (PA)), triphenylphosphine as a curing accelerator, and γ-glycidoxypropyltrimethoxysilane as a silane coupling agent. A resin composition was prepared according to the composition shown, and molded at 150 ° C. for 3 minutes to obtain a cured test piece. The test piece was 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 a value obtained by molding a disk of 50 mmΦ × 3 mmt using these epoxy resin compositions, post-curing, and then absorbing moisture for a predetermined time at 85 ° C. and 85% RH. The crack occurrence rate is QFP-
After molding 80 pins (14 × 20 × 2.5 mt) and post-curing, after absorbing moisture for a predetermined time under the same conditions as the water absorption,
After being immersed in a 260 ° C. solder bath for 10 seconds, the state of the package was observed and determined.

[0033]

[Table 1]

[0034]

[Table 2]

[0035]

The epoxy resin composition of the present invention, that is, a novel epoxy resin represented by the general formula (3) or an epoxy resin containing the same as an epoxy resin component, or a epoxy resin composition represented by the general formula (1) as a curing agent component A cured product obtained by curing an epoxy resin composition obtained by blending at least one of a polyvalent hydroxy compound or a polyvalent hydroxy resin containing the same as an essential component is excellent in moisture resistance and heat resistance, In addition, it has excellent mechanical properties such as impact resistance, and can be suitably used for applications such as lamination, molding, casting, and adhesion.

[Brief description of the drawings]

FIG. 1 shows the GP of the polyvalent hydroxy resin obtained in Example 1.
It is a C chart.

FIG. 2 is an infrared absorption spectrum of the polyvalent hydroxy resin obtained in Example 1.

FIG. 3 shows the H-type of the polyvalent hydroxy resin obtained in Example 1.
It is an NMR spectrum.

FIG. 4 shows the GP of the polyvalent hydroxy resin obtained in Example 2.
It is a C chart.

FIG. 5 is an infrared absorption spectrum of the polyvalent hydroxy resin obtained in Example 2.

FIG. 6 shows the H-type of the polyvalent hydroxy resin obtained in Example 2.
It is an NMR spectrum.

FIG. 7 is a GPC chart of the epoxy resin obtained in Example 3.

FIG. 8 is an infrared absorption spectrum of the epoxy resin obtained in Example 3.

FIG. 9 shows H-NMR of the epoxy resin obtained in Example 3.
It is a spectrum.

FIG. 10 is a GPC chart of the epoxy resin obtained in Example 4.

FIG. 11 is an infrared absorption spectrum of the epoxy resin obtained in Example 4.

FIG. 12 shows H-NM of the epoxy resin obtained in Example 4.
It is an R spectrum.

Continuation of the front page (51) Int.Cl. ⁶ Identification code FI C08G59 / 24 C08G59 / 24 // C07B 61/00 300 C07B 61/00 300 (72) Inventor Shota Shirasaka Oita-shi Oita-shi No. 3 Nippon Steel Chemical Co., Ltd. Oita Office

Claims (7)

[Claims] 1. A novel polyvalent hydroxy compound represented by the following general formula (1). Embedded image (Wherein, A represents a benzene ring or a naphthalene ring which may be substituted with an alkyl group having 1 to 6 carbon atoms, R represents a hydrogen atom or a methyl group, n represents a number of 0 to 15, m
Represents an integer of 1 to 3) 2. A phenolic compound represented by the following general formula (2):
The polyhydric hydroxy resin containing the novel polyhydric hydroxy compound according to claim 1, which is obtained by reacting with a crosslinking agent containing at least 50% of divinylnaphthalenes represented by the formula: Embedded image (Wherein, R represents a hydrogen atom or a methyl group) 3. An amount of 0.1 to 1 mol of the phenolic compound.
The method for producing a polyvalent hydroxy resin according to claim 2, wherein a crosslinking agent containing 50 to 0.9 mol of divinylnaphthalenes in an amount of 50 to 0.9 mol is reacted in the presence of an acidic catalyst. 4. A novel epoxy resin represented by the following general formula (3). Embedded image (Wherein, A represents a benzene ring or a naphthalene ring which may be substituted with an alkyl group having 1 to 6 carbon atoms, R represents a hydrogen atom or a methyl group, G represents a glycidyl group, n
Represents a number of 0 to 15, and m represents an integer of 1 to 3) 5. An epoxy resin containing the novel epoxy resin according to claim 4, which is obtained by reacting the polyhydroxy resin according to claim 2 with epichlorohydrin. 6. An epoxy resin composition comprising an epoxy resin and a curing agent, wherein the epoxy resin comprises at least one of the epoxy resin according to claim 5 and the polyhydroxy resin according to claim 2 as an essential component. Resin composition. 7. A cured product obtained by curing the epoxy resin composition according to claim 6.