JP4742625B2 - Hydrogenated epoxy resin, method for producing the same, and epoxy resin composition - Google Patents

Description

  The present invention relates to a novel hydrogenated epoxy resin, a method for producing the same, and an epoxy resin composition in which the hydrogenated epoxy resin and an epoxy resin curing agent are blended.

  Since the cured product obtained from the hydrogenated epoxy resin of the present invention is excellent in flame retardancy and moisture resistance, it is useful for applications such as semiconductor sealing materials, resist materials, electrical insulating materials, and laminates.

  Epoxy resins are excellent in heat resistance, adhesion, water resistance, mechanical strength, electrical properties, etc., so they are used in various fields such as adhesives, paints, materials for civil engineering and construction, insulating materials for electrical and electronic parts, etc. in use. As normal temperature or heat-curing type epoxy resins, conventionally, aromatic epoxy resins such as diglycidyl ether of bisphenol A, diglycidyl ether of bisphenol F, phenol or cresol novolac type epoxy resin are generally used. in use.

  However, with the advancement of technology, there is an increasing demand for higher performance of epoxy resins, and the current situation is that conventional epoxy resins as described above cannot meet the demands. For example, in the field of electrical and electronic applications, with the progress of miniaturization and thinning technology of electronic components, it is necessary for resin to sufficiently enter into narrow gaps inside the miniaturized components. An epoxy resin having low melt viscosity and high heat resistance that can withstand the generated heat is desired.

  In order to solve these problems, a technique using an epoxy resin having crystallinity at room temperature or higher has been proposed. For example, tetramethylbiphenyl type epoxy resin (Patent Document 1), stilbene type epoxy resin (Patent Document 2), and the like. However, since these compounds have a bulky substituent near the epoxy group, they have a high melt viscosity and are not sufficient in terms of curability. Moreover, the hardened | cured material using these epoxy resins is inadequate in terms of a flame retardance and moisture resistance.

Then, the epoxy resin composition containing the new epoxy resin which increased the number of the aromatic rings in 1 molecule and improved the flame retardance compared with the conventional epoxy resin is proposed (patent document 3). However, since the cured product obtained by curing this aromatic epoxy resin has many aromatic rings in the molecule, the flame retardancy is improved, but the melt viscosity is increased and the moisture resistance is further decreased. There is a problem that it cannot be applied to applications that require workability and reliability characteristics.
Japanese Patent Publication No. 7-53791 Japanese Patent Laid-Open No. 9-12673 JP 2002-128868 A

  The present invention is a novel hydrogenated epoxy resin that is solid at room temperature, has excellent handleability, has extremely low melt viscosity, has excellent reactivity with a curing agent, and provides a cured product with excellent flame retardancy and moisture resistance, The manufacturing method and the epoxy resin composition are provided.

  The present invention includes the following inventions.

［（１）式中、Ｒ¹〜Ｒ ^６ は水素原子、Ｒ ^７ 及びＲ⁸は各々独立に水素原子又はメチル基を示し、ｎは０以上の数を示す。］ [1] represented by the following general formula (1), hydrogenated epoxy resin epoxy equivalent is characterized 170-250 der Rukoto.

[In formula (1), R ¹ to R ⁶ each independently represent a hydrogen atom, R ⁷ and R ⁸ each independently represent a hydrogen atom or a methyl group, and n represents a number of 0 or more. ]

［（２），（３）式中、Ｒ¹〜Ｒ ^６ は水素原子、Ｒ ^７ 及びＲ⁸は各々独立に水素原子又はメチル基を示し、ｎは０以上の数を示す。］ [2] A method for producing a hydrogenated epoxy resin represented by the above general formula (1) and having an epoxy equivalent of 170 to 250, wherein the anthracene type epoxy resin represented by the following general formula (2) and / or A method of directly hydrogenating a dihydroanthracene-type epoxy resin represented by the general formula (3) in the presence of a hydrogenation catalyst, wherein the hydrogenation catalyst is supported on a rhodium catalyst and / or a ruthenium catalyst supported on a carbon carrier. It is a catalyst, the usage-amount of this hydrogenation catalyst is 5-10 mass parts with respect to 100 mass parts of raw material epoxy resins, reaction pressure is 1-30 Mpa, reaction temperature is 30-150 degreeC, reaction time is 0.5. It is -20 hours, The manufacturing method of the hydrogenated epoxy resin as described in [1] characterized by the above-mentioned.

[In the formulas (2) and (3), R ¹ to R ⁶ each independently represent a hydrogen atom, R ⁷ and R ⁸ each independently represent a hydrogen atom or a methyl group, and n represents a number of 0 or more. ]

[3] The anthracene-type epoxy resin and / or manufacturing method of the hydrogenated epoxy resin according to dihydroanthracene type epoxy resin, characterized in that hydrogenation in the presence of Solvent [2].

[ 4 ] An epoxy resin composition comprising the hydrogenated epoxy resin according to [1] and an epoxy resin curing agent.

[ 5 ] The epoxy resin curing agent is composed of amines, acid anhydrides, polyhydric phenols, imidazoles, Bronsted acid salts, dicyandiamides, BF ₃ complex compounds of amines, organic acid hydrazides and polycarboxylic acids. The epoxy resin composition according to [ 4 ], which is one or more selected from the group consisting of:

  The hydrogenated epoxy resin of the present invention has a low viscosity at the time of melting, and the cured product becomes a material excellent in flame retardancy and moisture resistance. Therefore, a semiconductor encapsulating material, a resist material, an electrical insulating material, and an epoxy for laminates It can be advantageously used as a resin.

  Below, the hydrogenated epoxy resin of this invention, its manufacturing method, and embodiment of an epoxy resin composition are described in detail.

(Hydrogenated epoxy resin)
The hydrogenated epoxy resin of the present invention is represented by the following general formula (1), preferably an anthracene type epoxy resin represented by the following general formula (2) and / or a dihydroanthracene type epoxy represented by the following general formula (3). Obtained by direct hydrogenation of the resin.

［（１）〜（３）式中、Ｒ¹〜Ｒ⁸は水素原子又は炭素数１〜６のアルキル基を示し、ｎは０以上の数を示す。］

[In the formulas (1) to (3), R ^{1 to} R ⁸ represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, and n represents a number of 0 or more. ]

  The anthracene type epoxy resin can be produced by a known method in which a dihydroxyanthracene represented by the following general formula (4) and epichlorohydrin are dehydrochlorinated in the presence of an alkali such as sodium hydroxide.

［（４）式中、Ｒ¹〜Ｒ⁸は各々独立に水素原子又は炭素数１〜６のアルキル基を示す。］

[In the formula (4), R ^{1 to} R ⁸ each independently represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. ]

  The dihydroanthracene-type epoxy resin can be produced by a known method in which a dihydroanthrahydroquinone represented by the following general formula (5) and epichlorohydrin are dehydrochlorinated in the presence of an alkali such as sodium hydroxide.

［（５）式中、Ｒ¹〜Ｒ⁸は各々独立に水素原子又は炭素数１〜６のアルキル基を示す。］

[In formula (5), R < ¹ > -R < ⁸ > shows a hydrogen atom or a C1-C6 alkyl group each independently. ]

Among the anthracene type epoxy resin represented by the general formula (2) and the dihydroanthracene type epoxy resin represented by the general formula (3) obtained by performing the epoxidation reaction by dehydrochlorination, R ¹ to R ⁶ is a hydrogen atom, R ⁷ and R ⁸ is a hydrogen atom or a methyl group (in this case, either one of R ⁷ and R ⁸ are hydrogen atoms, than the other is a methyl group, R ⁷ and R ⁸ Both are preferably hydrogen atoms or methyl groups.) A hydrogenated epoxy resin obtained by hydrogenating an epoxy resin is preferable in terms of excellent balance between heat resistance and moisture resistance of a cured product. Furthermore, it is particularly preferable to use a dihydroanthracene type epoxy resin as a raw material from the viewpoint of easy hydrogenation reaction.

  The hydrogenated epoxy resin of the present invention can be obtained by hydrogenating a carbon-carbon double bond and an aromatic nucleus in the presence of a solvent and a hydrogenation catalyst with the anthracene type epoxy resin and / or dihydroanthracene type epoxy resin. In this case, as the raw material, either an anthracene type epoxy resin or a dihydroanthracene type epoxy resin may be used, or both an anthracene type epoxy resin and a dihydroanthracene type epoxy resin may be used. Two or more different anthracene type epoxy resins may be used, or two or more different dihydroanthracene type epoxy resins may be used. However, as described above, it is preferable to use a dihydroanthracene type epoxy resin as a raw material.

  As the hydrogenation catalyst, various heterogeneous catalysts or homogeneous catalysts can be used. Among them, heterogeneous catalysts are preferable because of easy catalyst separation, and nickel-based catalysts and platinum group catalysts are preferably used. Is done. The nickel-based catalyst can be used as a Raney catalyst or supported on a carrier such as diatomaceous earth or alumina. The platinum group catalyst is mainly used as supported on a carrier.

  Among these hydrogenation catalysts, platinum group catalysts are particularly preferable, and among them, rhodium or ruthenium-based catalysts moderate carbon-carbon double bonds and aromatic nuclei by suppressing hydrogenolysis of the contained epoxy groups. Since it can hydrogenate on conditions, it is preferable. As the catalyst carrier, carbon-based carriers such as activated carbon and graphite, and inorganic carriers such as silica and alumina are preferably used. A catalyst may be used individually by 1 type and may use 2 or more types together. The amount of the hydrogenation catalyst used is preferably about 0.1 to 10 parts by mass with respect to 100 parts by mass of the raw material epoxy resin.

  The hydrogenation reaction solvent is used to dissolve the epoxy resin and allow the reaction to proceed smoothly. However, an ether solvent or an ester solvent is preferable because the solubility of the epoxy resin and the hydrogenation reaction hardly affect the reaction. used. As the ether solvent, tetrahydrofuran, methyltetrahydrofuran, dioxane and the like can be used, and as the ester solvent, various solvents such as ethyl acetate, butyl acetate and methyl propionate can be used. As the hydrogenation reaction solvent, one of these may be used alone, or two or more may be mixed and used. It is preferable that the usage-amount of a solvent shall be about 20-90 mass% with respect to raw material epoxy resin.

  The reaction conditions for the hydrogenated epoxy resin of the present invention may be selected so that the pressure is 1 to 30 MPa and the temperature is about 30 to 150 ° C., depending on the degree of hydrogenation of the catalyst and the raw material epoxy resin. In general, the reaction time is adjusted to be about 0.5 to 20 hours so that the production is easy.

  As an example of a more preferred reaction method, a dihydroanthracene type epoxy resin is dissolved in an ester solvent and / or an ether solvent, and a platinum catalyst, more preferably a catalyst in which rhodium and / or ruthenium is supported on graphite and / or activated carbon. The method of hydrogenating using is mentioned. After completion of the reaction, the hydrogenated epoxy resin of the present invention can be obtained by removing the catalyst from the reaction product solution by filtration and distilling off the organic solvent under reduced pressure until it substantially disappears.

  The hydrogenated epoxy resin of the present invention thus produced varies depending on the molecular weight, but usually has an epoxy equivalent of 170 to 250, a melting point of 70 to 150 ° C., and 150 measured with a cone plate viscometer. The melt viscosity at ° C is preferably 2 to 50 mPa · s.

(Curing agent for epoxy resin)
The epoxy resin composition of the present invention comprises the above-described hydrogenated epoxy resin of the present invention and a curing agent for epoxy resin. As the curing agent for epoxy resin, a general curing agent for epoxy resin is used, and examples thereof include the following.

  (1) Amines: bis (4-aminocyclohexyl) methane, bis (aminomethyl) cyclohexane, m-xylylenediamine, 3,9-bis (3-aminopropyl) -2,4,8,10-tetraspiro [ 5,5] Aliphatic and alicyclic amines such as undecane, aromatic amines such as metaphenylenediamine, diaminodiphenylmethane, diaminodiphenylsulfone, benzyldimethylamine, 2,4,6-tris (dimethylaminomethyl) pheno And tertiary amines such as 1,8-diazabicyclo- (5,4,0) -undecene-7, 1,5-azabicyclo- (4,3,0) -nonene-7 and salts thereof.

  (2) Acid anhydrides: aromatic anhydrides such as phthalic anhydride, trimellitic anhydride, pyromellitic anhydride, tetrahydrophthalic anhydride, methyl tetrahydrophthalic anhydride, hexahydrophthalic anhydride, methyl hexahexan anhydride Cyclic aliphatic acid anhydrides such as hydrophthalic acid, methylendomethylenetetrahydrophthalic anhydride, dodecenyl succinic anhydride, and trialkyltetrahydrophthalic anhydride.

  (3) Multivalent phenols: catechol, resorcin, hydroquinone, bisphenol F, bisphenol A, bisphenol S, biphenol, phenol novolacs, cresol novolacs, bisphenol Divalent phenol novolacs such as A, trishydroxyphenylmethanes, aralkylpolyphenols, dicyclopentadiene polyphenols and the like.

(4) Others: Imidazoles such as 2-methylimidazole and 2-ethyl-4-methylimidazole; BF ₃ complex compounds of amines as described above; aliphatic sulfonium salts, aromatic sulfonium salts, iodonium salts, phosphonium salts, etc. Bronsted acid salts of: organic acid hydrazides such as adipic acid dihydrazide and phthalic acid dihydrazide; dicyandiamides; polycarboxylic acids such as adipic acid, sebacic acid, terephthalic acid, trimellitic acid, and carboxyl group-containing polyester.

  These epoxy resin curing agents may be used alone or in combination of two or more.

  Although the compounding quantity of the hardening | curing agent for epoxy resins changes also with the kind of hardening | curing agent for epoxy resins to be used, it is 0.01-200 mass parts normally with respect to 100 mass parts of hydrogenated epoxy resins, Preferably it is 0.1-150. Within the range of parts by mass.

(Optional component)
In the epoxy resin composition of the present invention, the following components can be added and blended as necessary.

(A) Curing accelerator: phosphine compound, imidazole compound, diazabicyclo compound, and salts thereof.
The curing accelerator can be blended in an amount of 0.1 to 10 parts by mass with respect to 100 parts by mass of the hydrogenated epoxy resin.

(B) Powdery reinforcing agents and fillers; for example, metal oxides such as aluminum oxide and magnesium oxide, silicon compounds such as fine powder silica, fused silica and crystalline silica, transparent fillers such as glass beads, and aluminum hydroxide One or more of metal hydroxide, other, kaolin, mica, quartz powder, graphite, molybdenum disulfide and the like.
These are usually in the range of 10 to 1000 parts by mass with respect to 100 parts by mass of the hydrogenated epoxy resin.

(C) Colorant or pigment; for example, one or more of titanium dioxide, molybdenum red, bitumen, ultramarine blue, cadmium yellow, cadmium red, organic dye, and the like.
(D) Flame retardant; for example, one or more of antimony trioxide, bromine compound and phosphorus compound.
(E) Ion adsorbent.
(F) Property improvers such as coupling agents, antioxidants, ultraviolet absorbers and the like.
Said (c)-(f) can mix | blend 0.01-30 mass parts normally with respect to 100 mass parts of hydrogenated epoxy resins, respectively, and 0.1-30 mass parts in total.

Furthermore, various curable monomers, oligomers, synthetic resins and the like can be blended with the epoxy resin composition of the present invention for the purpose of improving the properties of the cured product.
For example, as an epoxy resin other than the hydrogenated epoxy resin of the present invention, bisphenol A, bisphenol F, bisphenol AD, biphenol, tetramethylbiphenol, terpene diphenol, hydroquinone, methylhydroquinone, dibutylhydroquinone, resorcin, methylresorcin, bisphenol S, Various phenols such as thiodiphenol, dihydroxydiphenyl ether, dihydroxynaphthalene, phenol novolak resin, cresol novolak resin, bisphenol A novolak resin, dicyclopentadiene phenol resin, terpene phenol resin, phenol aralkyl resin, biphenyl aralkyl resin, naphthol novolak resin And various phenols, hydroxybenzaldehyde, croto Modified phenol obtained by polycondensation of polyhydric phenol resin, petroleum heavy oil or pitches, formaldehyde polymer and phenols obtained by condensation reaction with various aldehydes such as aldehyde and glyoxal in the presence of an acid catalyst Epoxy resins produced from various phenolic compounds such as resins and epihalohydrin, epoxy resins produced from various amine compounds such as diaminodiphenylmethane, aminophenol and xylenediamine, and epihalohydrin, methylhexahydroxyphthalic acid, One type or two or more types of epoxy resins produced from various carboxylic acids such as dimer acid and epihalohydrin can be blended. In addition to these, diluents for epoxy resins such as glycidyl ethers of aliphatic alcohols, diols or triols, vinyl ethers, oxetane compounds, fluororesins, acrylic resins, silicone resins, and the like may be used. be able to.

  These compounds and resins are blended within a range that does not impair the original properties of the epoxy resin composition of the present invention, and are generally 50 parts by mass or less with respect to 100 parts by mass of the hydrogenated epoxy resin of the present invention. It is preferable to do.

Hereinafter, the present invention will be described in more detail with reference to Examples and Comparative Examples.
In the following, “part” means “part by mass”.

[Production example of hydrogenated epoxy resin]
The Example which manufactures the hydrogenated epoxy resin of this invention below is shown. In the following examples, various analysis methods for the obtained hydrogenated epoxy resin are as follows.

1) Epoxy equivalent In accordance with JIS K7236-1955, titration was performed with perchloric acid in the presence of acetic acid and cetyltrimethylammonium bromide, hydrogen bromide generated was added to the epoxy group, and the end point was determined by the potential difference.
2) ¹ H nuclear magnetic resonance spectrum About 0.02 g of a sample was dissolved in deuterated chloroform and measured at 400 MHz.
3) ¹³ C-NMR nuclear magnetic resonance spectrum About 0.1 g of a sample was dissolved in deuterated chloroform and measured at 100 MHz.
4) Infrared absorption spectrum The sample was dissolved in acetone, applied to a KBr plate, dried with a dryer, and then measured for transmission.

Example 1
In a 1 L autoclave, 150 g of dihydroanthracene type epoxy resin (epoxy equivalent; 178) represented by the following structural formula (3A), 300 g of ethyl acetate, and 7.5 g of 5 wt% rhodium / graphite catalyst as a catalyst were charged at 110 ° C. The hydrogenation reaction was performed under the condition of 8 MPa. Although hydrogen absorption was observed for about 30 minutes from the start of the reaction, the hydrogen absorption was extremely reduced. Therefore, after stirring for another 30 minutes, the mixture was cooled, depressurized and replaced with gas, and the reaction solution was extracted.

  Ethyl acetate and magnesium oxide powder (“AD100P” manufactured by Tomita Pharmaceutical Co., Ltd.) and a filter aid were added to the reaction solution, followed by filtration. The solvent was distilled off from the filtrate at 150 ° C. under reduced pressure, and the can liquid was cooled and solidified to obtain a crystalline solid epoxy resin.

When the obtained epoxy resin was analyzed by ¹ H-NMR, protons at a magnetic field lower than 5 ppm were not observed, and the unsaturated bond of the outer core was hydrogenated, but analysis by ¹³ C-NMR The aromatic ring of the inner core remained and was confirmed to be a hydrogenated epoxy resin represented by the following structural formula (1A).

  Moreover, the epoxy equivalent of the obtained hydrogenated epoxy resin was 201, and melting | fusing point was 111 degreeC. The melt viscosity at 150 ° C. measured with a cone plate viscometer was 10 mPa · s.

  The nuclear magnetic resonance spectrum of this hydrogenated epoxy resin is shown in FIG. 1, and the infrared absorption spectrum is shown in FIG.

Example 2
In a 1 L autoclave, 150 g of anthracene type epoxy resin (epoxy equivalent; 177) represented by the following structural formula (2A), 300 g of ethyl acetate and 10.5 g of 5 wt% rhodium / graphite catalyst as a catalyst were charged at 110 ° C. and 8 MPa. The hydrogenation reaction was carried out under the following conditions. Although hydrogen absorption was observed for about 90 minutes, the hydrogen absorption was extremely reduced. After stirring for another 30 minutes, the mixture was cooled, depressurized and replaced with gas, and the reaction solution was extracted.

  Ethyl acetate and magnesium oxide powder (“AD100P” manufactured by Tomita Pharmaceutical Co., Ltd.) and a filter aid were added to the reaction solution, followed by filtration. The filtrate was evaporated at 150 ° C. under reduced pressure, and the can liquid was cooled and solidified to obtain a crystalline solid.

Where the resulting product analyzed by ¹ H-NMR a, [delta] is but unsaturated bonds outside the nucleus not observed downfield proton from 5ppm had been almost completely hydrogenated, in the ¹³ C-NMR Analysis confirmed that the aromatic ring of the inner core remained and was a hydrogenated epoxy resin represented by the structural formula (1A). The epoxy equivalent of the obtained epoxy resin was 205, and melting | fusing point was 109 degreeC.

[Production Example and Curing Example of Epoxy Resin Composition]
Below, the Example and comparative example which manufacture the epoxy resin composition of this invention, and obtain a hardening body from the manufactured epoxy resin composition are given.

The raw materials other than the hydrogenated epoxy resin of the present invention used in the following are as follows.
<Other hydrogenated epoxy resins>
Bisphenol A type epoxy resin (“E828US” manufactured by Japan Epoxy Resin Co., Ltd.)
<Curing agent for epoxy resin>
a: Methyl hexahydrophthalic anhydride (“MH-700” manufactured by Shin Nippon Rika Co., Ltd.)
b: Trialkyltetrahydrophthalic anhydride (“YH306” manufactured by Japan Epoxy Resin Co., Ltd.)
<Curing accelerator>
Triphenylphosphine

Moreover, the measuring method of various physical properties thru | or a characteristic of an epoxy resin composition or hardened | cured material is as follows.
<Gelification time>
The measurement was performed at 100 ° C. using a gel time tester manufactured by Yasuda Seiki.
<Glass transition temperature Tg>
It was measured by the TMA method (temperature rising at 5 ° C./min).
<Hygroscopic rate>
About the disk-shaped hardened | cured material of thickness 3mm and diameter 50mm, the moisture absorption after 121 degreeC and 24 hours was measured. The smaller this value, the better the moisture resistance.

Examples 3-5, Comparative Example 1
In the formulation shown in Table 1, components other than the curing accelerator were mixed at a temperature of 70 ° C. until uniform, then the curing accelerator was added, stirred and dissolved to obtain an epoxy resin composition.
The physical properties of this epoxy resin composition were as shown in Table 1.

After defoaming this epoxy resin composition under reduced pressure, it was poured into a metal mold and cured in an oven at 100 ° C. for 3 hours and then at 140 ° C. for 3 hours to obtain a cured product.
The physical property values of the obtained epoxy cured product were as shown in Table 1.

From Table 1, it can be seen that the hydrogenated epoxy resin of the present invention has a low melt viscosity, and according to this hydrogenated epoxy resin, a cured product excellent in moisture resistance can be obtained.
In addition, although the evaluation about flame retardance is not performed in the above evaluation, the hydrogenated epoxy resin of the present invention has an aromatic ring remaining, and in particular, the glycidyl ether group is bonded to the aromatic ring so that it is flame retardant. Also excellent.

2 is a nuclear magnetic resonance spectrum of the hydrogenated epoxy resin obtained in Example 1. 2 is an infrared absorption spectrum of the hydrogenated epoxy resin obtained in Example 1.

Claims (5)

Is represented by the following general formula (1), hydrogenated epoxy resin epoxy equivalent is characterized 170-250 der Rukoto.

[In formula (1), R ¹ to R ⁶ each independently represent a hydrogen atom, R ⁷ and R ⁸ each independently represent a hydrogen atom or a methyl group, and n represents a number of 0 or more. ] A method for producing a hydrogenated epoxy resin represented by the following general formula (1) and having an epoxy equivalent of 170 to 250,
An anthracene type epoxy resin represented by the following general formula (2) and / or a dihydroanthracene type epoxy resin represented by the following general formula (3) is directly hydrogenated in the presence of a hydrogenation catalyst ,
The hydrogenation catalyst is a rhodium catalyst and / or a ruthenium catalyst supported on a carbon carrier;
The amount of the hydrogenation catalyst used is 5 to 10 parts by mass with respect to 100 parts by mass of the raw material epoxy resin,
The reaction pressure is 1 to 30 MPa, the reaction temperature is 30 to 150 ° C., method of producing a water-fluorinated epoxy resin you wherein the reaction time is 0.5 to 20 hours.

[In the formulas (1), (2), (3), R ¹ to R ⁶ each independently represent a hydrogen atom, R ⁷ and R ⁸ each independently represent a hydrogen atom or a methyl group, and n represents a number of 0 or more. ] Method for producing a hydrogenated epoxy resin according to claim 2, characterized in that hydrogenation in the presence of the anthracene type epoxy resin and / or a dihydro-anthracene-type epoxy resin Solvent.   An epoxy resin composition comprising the hydrogenated epoxy resin according to claim 1 and a curing agent for epoxy resin. The epoxy resin curing agent is selected from the group consisting of amines, acid anhydrides, polyhydric phenols, imidazoles, Bronsted acid salts, dicyandiamides, BF ₃ complex compounds of amines, organic acid hydrazides and polycarboxylic acids. The epoxy resin composition according to claim 4 , wherein the epoxy resin composition is one or more selected.

Images