JPH1087792A - Epoxy resin composition and its production - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain the subject composition containing a specific polyhydroxy compound, capable of giving cured products excellent in heat resistance, mechanical characteristics, etc., from simply produced raw materials in states saved in energy and reduced in drainage, and useful in the field of electric and electronic parts, etc. SOLUTION: This epoxy resin composition comprises (A) highly pure 1,1,2,2- tetrakis(4-hydroxy-3,5-dimethyphenyl)ethane obtained by subjecting (A) the two molecules of (A1 ) bis(3,5-dimethyl-4-hydroxyphenyl) methane to a dehydrogenation condensation, and (B) an epoxy resin. The components A and B are contained so that the OH of the component A is contained in an amount of 0.5-2 moles per mole of the epoxy group of the component B. The component A is obtained e.g. by blowing air or oxygen into the melted component A1 at a temperature of 180-300 deg.C in the absence of a catalyst and simultaneously subjecting the component A1 to a dehydrogenation condensation reaction.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

[0001] The present invention relates to an epoxy resin composition and a method for producing the same. Specifically, the present invention relates to
Epoxy resin derived from 1,2,2-tetrakis (4-hydroxy-3,5-dimethylphenyl) ethane,
1,1,2,2-tetrakis (4-hydroxy-3,5
The present invention relates to an epoxy resin composition containing (-dimethylphenyl) ethane as a curing agent, and a method for producing the epoxy resin composition.

[0002]

2. Description of the Related Art 1,1,2,2-Tetrakis (4-hydroxy-3,5-dimethylphenyl) ethane (hereinafter abbreviated as TKXE) is a raw material for producing phenolic resins and epoxy resins, or Used as a curing agent for epoxy resins.

For example, JP-A-64-74213 discloses an epoxy resin composition in which an epoxy compound obtained by epoxidizing TKXE and TKXE as a curing agent are mixed at a specific composition ratio. TKXE used in the epoxy resin composition is obtained by condensing 2,6-xylenol and glyoxal in the presence of an acidic catalyst.

[0004] Glyoxal is very unstable in the anhydrous state and is usually marketed as a 40-50% by weight aqueous solution. Use of such aqueous glyoxal for the condensation of 2,6-xylenol with glyoxal results in a condensation reaction in the presence of water. When 2,6-xylenol is condensed with glyoxal in the presence of water, a large amount of low molecular weight substances such as condensates of glyoxal and the like are produced as by-products in addition to TKXE, and this low molecular weight substance is separated from TKXE. TKXE cannot be obtained.

Accordingly, TK obtained by condensation of 2,6-xylenol and glyoxal in the presence of an acidic catalyst.
When XE is used as a raw material for producing an epoxy resin or as a curing agent for an epoxy resin, TKXE of low purity containing a low molecular weight substance or the like must be used.

TKXE containing a large amount of a low molecular weight substance such as a condensate of glyoxal is used as a raw material for producing an epoxy resin,
Or, when used as a curing agent for an epoxy resin, the heat resistance, mechanical properties, etc. of the cured product obtained therefrom are reduced. There is a problem when used as

JP-A-63-223020 discloses that when a phenol is subjected to a condensation reaction with a dialdehyde such as glyoxal or glutaraldehyde in the presence of an acid catalyst, the concentration of water in the reaction system is 2% by weight. A method for producing polyphenols, which is characterized by the following, is disclosed.

[0008] However, this method requires that the concentration of water in the reaction system be 2 or less.
It is only specified to be less than% by weight, and there is no difference from the conventional method in that dialdehydes are used as an aqueous solution. Therefore, it is necessary to remove a large amount of water charged into the reaction system by distillation or the like prior to the condensation reaction, and to adjust the amount of water in the reaction system to 2% by weight or less. Therefore, not only is the operation complicated, but also extra energy is consumed to distill and remove the large amount of water.

In addition, the water removed from the reaction system cannot be discharged to the outside of the plant without treatment because it contains a large amount of organic substances. Therefore, for example, a water purification device such as an activated sludge treatment device is required. Furthermore, since the phenols and the dialdehydes are still condensed in the presence of water even though the content is 2% by weight or less, the production of low molecular weight substances such as condensates of glyoxal can be completely suppressed. However, this method is not always satisfactory as a method for producing high-purity TKXE.

[0010]

SUMMARY OF THE INVENTION An object of the present invention is to eliminate the above-mentioned complicated operations and extra energy,
High-purity 1,1,2,2-tetrakis (4-hydroxy-) which does not generate a large amount of wastewater containing organic matter.
According to a method for producing 3,5-dimethylphenyl) ethane (TKXE), it is possible to provide an epoxy resin, an epoxy resin composition, and a method for producing the same, which can provide a cured product having excellent heat resistance, mechanical properties, and the like. is there.

[0011]

Means for Solving the Problems The present inventors have conducted intensive studies to achieve the above object, and as a result, have found that two molecules of bis (3,5
-Dimethyl-4-hydroxyphenyl) methane (hereinafter, referred to as
It has been found that high purity TKXE can be obtained by dehydrocondensation of bisxylenol F (abbreviated as BXF). Furthermore, the high-purity TK obtained as described above
The cured product of the epoxy resin obtained by epoxidizing XE and the cured product of the epoxy resin composition containing TKXE of high purity obtained as described above as a curing agent have excellent heat resistance and mechanical properties. I found that.

The method of producing TKXE of the present invention is characterized in that TKXE can be obtained as high-purity crystals, unlike the conventional production method. Therefore, when this is used as a raw material for producing an epoxy resin, or as a curing agent for an epoxy resin, a cured product having excellent heat resistance, mechanical strength, and electrical properties is obtained, and the cured product is It is suitable for use in electrical and electronic parts. T obtained by the method of the present invention
KXE can also be used as a raw material of a phenol resin.

A first aspect of the present invention is a high purity TKX obtained by dehydrocondensing two molecules of BXF under oxidizing conditions.
An epoxy resin obtained by epoxidizing E, and 2
BXF of the molecule is subjected to dehydrocondensation under oxidizing conditions to produce high-purity TKXE, and the product is epoxidized with epihalohydrin at a temperature of 40 to 120 ° C. in the presence of a hydrogen halide acceptor. This is a method for producing an epoxy resin.

A second aspect of the present invention is a high purity TKX obtained by dehydrocondensing two molecules of BXF under oxidizing conditions.
Epoxy resin containing E (A) and epoxy resin (B), wherein the amount of (A) and (B) is 0.5 to 2 moles of hydroxyl group of (A) per mole of epoxy group of (B) The composition and two molecules of BXF are subjected to dehydrocondensation under oxidizing conditions to produce high-purity TKXE (A), and (A) and the epoxy resin (B) are converted to 1 mol of the epoxy group of (B). A method for producing an epoxy resin composition, characterized in that (A) is mixed in such an amount that the hydroxyl groups become 0.5 to 2 mol.

[0015]

BEST MODE FOR CARRYING OUT THE INVENTION In the method for producing TKXE used in the present invention, two molecules of the formula (1) are prepared under oxidizing conditions.

[0016]

Embedded image BXF represented by the formula (2)

[0017]

Embedded image And one molecule of TKXE and one molecule of water.

The BXF used in the production of TKXE is not particularly limited, and may be produced by a known method. For example, 2,6-xylenol and formalin are reacted with phosphoric acid as a catalyst in the presence of n-butanol.
It is obtained by performing a condensation reaction at ~ 90 ° C.
In this case, even if low-molecular-weight products such as condensates of formalin are produced as by-products, they are used together with BXF when producing TKXE.
Since it can be easily separated from XE, the purity of TKXE does not decrease.

In the production of TKXE, two molecules of BXF
Dehydrocondensation proceeds in any state under oxidizing conditions. It may be under pressure, reduced pressure or normal pressure. A preferred production method is a method in which dehydrocondensation of two molecules of BXF is performed in an atmosphere containing an oxygen-containing gas such as air or oxygen. In order to increase the reaction rate, it is preferable to forcibly blow air or oxygen into the reaction system. The amount of air to be blown is not particularly limited and varies depending on the reaction temperature, the presence or absence of a catalyst, and the like.
10 to 1000 ml / min. It is about. When oxygen is used, about one-fourth is sufficient. The air or oxygen blown into the reaction system passes through a reflux condenser or the like and is exhausted outside the system.

That is, in the production of TKXE used in the present invention, the dehydrocondensation reaction proceeds by heating BXF in a normal air atmosphere in the absence of a catalyst,
TKXE is obtained. Alternatively, the BXF may be heated to a molten state, and the dehydrocondensation reaction may be performed while forcibly blowing air or oxygen into the melt. Furthermore, the reaction rate can be increased by performing the dehydrocondensation reaction while blowing air or oxygen in the presence of the oxidation catalyst.

The dehydrocondensation reaction in the present invention is carried out at room temperature to 3
It is preferable to carry out in the range of 10 ° C. In the presence of an oxidation catalyst, the dehydrocondensation reaction proceeds even at a temperature lower than room temperature, but is not preferred because the reaction rate is low. Also, 3
If it exceeds 10 ° C., TKXE is decomposed, which is not preferable.

When the dehydrocondensation reaction is carried out in the absence of a catalyst, the temperature is preferably in the range of 150 to 310 ° C. 150 ° C
A lower value is not preferable because the reaction rate is low. The most preferred method for performing the dehydrocondensation reaction in the absence of a catalyst is to perform the dehydrocondensation reaction at 180 to 300 ° C. while blowing air or oxygen into the molten BXF. In this case, the generated TKXE precipitates as crystals. Therefore, after completion of the reaction, TKXE can be obtained as crystals by filtering the reaction mixture while maintaining the reaction temperature at the reaction temperature. The obtained TKXE crystal was converted to B
By washing with a solvent that dissolves XF and does not dissolve TKXE, TKXE with higher purity can be obtained. BXF may be dissolved in a similar solvent to form a solution, and the dehydrocondensation reaction may be performed while blowing air or oxygen into the solution.

When a dehydrocondensation reaction is performed using an oxidation catalyst, the raw material BXF and the oxidation catalyst are dissolved in a solvent to form a solution, and the condensation reaction is performed while blowing air or oxygen into the solution. The reaction temperature in this case is from room temperature to 150 ° C.
Is preferred. The oxidation catalyst to be used is not particularly limited, and any catalyst that is usually used as an oxidation catalyst can be used. For example, copper oxide, molybdenum oxide,
Examples include metal oxides such as zinc oxide, cobalt oxide, and vanadium pentoxide, vanadium tetrachloride, lead chloride, and lead tetraacetate.

In addition, BXF to TKXE can be used in the presence of an oxidizing agent such as potassium permanganate and potassium dichromate.
Is generated, but BXF itself is oxidized and the yield tends to decrease, which is not preferable.

The dehydrocondensation reaction under any of the above conditions can be performed, for example, by installing a reflux condenser in the reactor.
It is preferable to sequentially discharge and remove water generated by the dehydrocondensation reaction to the outside of the system.

Solvents that can be used in the dehydrocondensation reaction, or that can be used for washing the obtained TKXE, include methanol, ethanol, propanol, butanol, pentanol, hexanol, octanol and nonanol. Examples thereof include aliphatic alcohols, aromatic alcohols such as benzyl alcohol, aromatic compounds such as benzene, toluene and xylene, ethers such as dimethyl ether, methyl ethyl ether and diethyl ether, and acetonitrile. These may be used alone or as a mixture. Of these, those preferably used are solvents that are liquid at the reaction temperature and / or the washing temperature. It is preferable to use a solvent that is liquid at the reaction temperature because the reaction can be performed at normal pressure.

The amount of the solvent that can be used in the dehydrocondensation reaction may be an amount that can completely dissolve BXF, and is generally about the same weight to about 10 times the weight of BXF. The amount of the solvent used for washing the obtained TKXE is preferably about the same weight to about 100 times the weight of TKXE. There is no particular limitation on the method of washing TKXE using a solvent. For example, the extraction treatment may be performed using a Soxhlet extractor or the like, or TKXE may be suspended in a solvent and stirred at room temperature to a temperature lower than the boiling point of the solvent.

The TKXE obtained according to the present invention is used as a raw material for producing phenol resins and epoxy resins. It is also suitably used as a curing agent for epoxy resins.

The TKXE obtained according to the present invention can be converted into an epoxy resin by a known method. That is, 40 to 12 in the presence of a hydrogen halide acceptor.
In the temperature range of 0 ° C., the TKX obtained according to the present invention
Epoxidation of E with epihalohydrin, preferably epichlorohydrin, gives an epoxy resin.

Examples of the hydrogen halide acceptor include alkali metal hydroxides such as potassium hydroxide and sodium hydroxide. A hydrogen halide acceptor is slowly added to the heated mixture of TKXE and epihalohydrin to raise the pH of the reaction mixture to about 6.5.
It is desirable to maintain it at -10.

The epihalohydrin used in the epoxidation reaction is 2.0 to 3 with respect to 1 equivalent of the OH group of the TKXE.
It is used in an amount equivalent to 0 equivalents, preferably an excess of 2.0 to 10 equivalents of epihalohydrin. The method of removing excess acceptor substances and by-produced salts from the reaction product is usually performed by means such as washing with water.

The TKXE obtained according to the present invention can be used as a curing agent for other epoxy resins as well as the above-mentioned curing agent for epoxy resins. Other epoxy resins include phenol novolak type, phenol aralkyl type, dicyclopentadiene modified phenol type, phenol type glycidyl ether type epoxy resin such as resol type phenol type, alcohol type such as butanediol type, polyethylene glycol type and polypropylene glycol type. Glycidyl ether type epoxy resin, phthalic acid type, isophthalic acid type, terephthalic acid type, carboxylic acid glycidyl ester type epoxy resin such as tetrahydrophthalic acid type, aniline type, active hydrogen bonded to nitrogen atom such as isocyanuric acid type An epoxy resin substituted with a glycidyl group, an alicyclic epoxy resin obtained by epoxidizing an intramolecular olefin, and the like are exemplified.

Epoxy resin and curing agent TKXE
Is preferably used in a mixing ratio such that the phenolic hydroxyl group of TKXE is 0.5 to 2 mol per mol of epoxy group of the epoxy resin. Even if less than 0.5 mole,
Further, if the amount exceeds 2 mol, the heat resistance, mechanical strength, and the like of the obtained cured product tend to decrease, which is not preferable.

Further, a curing accelerator may be added to the epoxy resin composition comprising the above-mentioned epoxy resin and TKXE obtained according to the present invention in order to shorten the curing reaction time between the epoxy resin and the phenolic hydroxyl group. it can. Examples of the curing accelerator include 2-methylimidazole and 2-methylimidazole.
Imidazoles such as ethyl-4-methylimidazole, 2-phenylimidazole, 2-phenyl-4-methylimidazole, tertiary amines such as tris (dimethylaminomethyl) phenol, triethylenediamine, benzyldimethylamine, triphenylphosphine, tributyl Examples include organic phosphines such as phosphine, tricyclohexylphosphine, and methyldiphenylphosphine, and diazabicycloalkenes such as 1,8-diazabicyclo (5,4,0) undecene-7. The addition amount of these curing accelerators is preferably 0.001 to 5% by weight based on the epoxy resin. If the addition amount is outside the above range, the heat resistance, mechanical properties and the like of the obtained cured product tend to decrease, which is not preferable.

The epoxy resin composition of the present invention may contain, as an inorganic filler, crystalline silica, fused silica, alumina, clay, titanium white, zircon, beryllia, magnesia, zirconia, forsterite, steatite, spinel, mullite. , Titania, barium sulfate, quartz glass, aluminum hydroxide, potassium titanate, silicon carbide, silicon nitride, alumina, glass fiber and the like can be added alone or as a mixture of two or more.

The epoxy resin composition of the present invention may further contain, if necessary, higher fatty acids, metal salts of higher fatty acids, esters, natural waxes, synthetic waxes, acid amides,
Release agents such as paraffin, bromine compounds, flame retardants such as antimony and phosphorus, coloring agents such as carbon black, silane coupling agents such as epoxy silane, amino silane, vinyl silane, alkyl silane, organic titanate, and others, flexible An additive such as a property imparting agent may be appropriately blended.

The method for producing the epoxy resin composition of the present invention using the above-mentioned raw materials is not particularly limited. As a general method, a method in which each raw material having a predetermined blending amount is sufficiently mixed by a mixer or the like, then kneaded using a hot roll, a screw type extruder, or the like, cooled, and pulverized can be exemplified.

[0038]

The present invention will be described below in detail with reference to examples.

Example 1 2.0 g of BXF and 5.0 g of 2-ethylhexanol were charged into a heat-resistant glass container equipped with a stirrer, a reflux condenser and a temperature controller, and stirred to convert BXF into 2-ethylhexanol. Dissolved. At 150 ° C., air was added to the solution at 30 ml / min. The dehydrocondensation reaction was carried out while blowing at a speed of. The air blown into the reaction system
It was discharged out of the system through a reflux condenser together with the generated water.
At about one hour, TKXE crystals started to precipitate. The reaction was completed in about 6 hours.

After cooling to room temperature, the reaction mixture was filtered,
TKXE crystals were obtained. The obtained crystal of TKXE was 10
g of methanol and washed with stirring at 60 ° C. for 5 minutes to remove unreacted BXF and by-products.
This was filtered, dried at 100 ° C. for 2 hours, and TKX
0.18 g of white crystals of E was obtained.

The obtained white crystals were analyzed using high performance liquid chromatography (HPLC), and the purity was 99.5.
% By weight. In addition, as a result of analysis by a nuclear magnetic resonance spectrum and a mass spectrometry spectrum, it was confirmed to be TKXE. As a result of elemental analysis, the theoretical value was C:
80% and H: 7.5%, whereas the actually measured value is C: 7
9%, H: 8.0%. In addition, T
It was 313 degreeC as a result of measuring the decomposition temperature of KXE. T
FIG. 1 shows the infrared absorption spectrum of KXE, and FIG. 2 shows the nuclear magnetic resonance spectrum. In FIG. 2, curve A shows a nuclear magnetic resonance spectrum, and curve B shows an integral curve of the nuclear magnetic resonance spectrum.

Example 2 The same container as in Example 1 was charged with 2.0 g of BXF,
C. to melt the BXF. Air was added to the melt at 30 ml / min. The dehydrocondensation reaction was carried out while blowing at a speed of. Water generated during the reaction was discharged out of the system through a reflux condenser. In about 1 hour, TKXE crystals started to precipitate. The reaction was completed after about 3 hours. Next, the reaction mixture obtained at the reaction temperature was filtered, and the raw material BXF in a molten state was separated by filtration. After cooling the obtained TKXE crystal to room temperature, it is put into 10 g of methanol,
The mixture was washed with stirring at 5 ° C. for 5 minutes to remove slightly adhered unreacted BXF and by-products. Filter this
After drying, 0.18 g of TKXE white crystals were obtained.

Examples 3 to 6 TKXE was obtained in the same manner as in Example 2 except that the conditions shown in Table 1 were used. The results obtained are shown in [Table 1].

Example 7 TKXE was obtained in the same manner as in Example 1 except that "air blowing" in Example 1 was changed to "oxygen blowing". The results obtained are shown in [Table 1].

Examples 8 to 12 The same procedures as in Example 2 were carried out except that the "air blowing" in Example 2 was replaced with the "oxygen blowing" method. The results obtained are shown in [Table 1].

Example 13 In the same container as in Example 1, BXF (10 g) and methanol (50) were added.
g and 7.5 g of vanadium tetrachloride were added and stirred at 40 ° C. to obtain a methanol solution. 40 under air atmosphere
The dehydrocondensation reaction was carried out at 2 ° C for 2 hours. The reaction mixture was filtered, and the obtained crystals were placed in 200 g of a mixed solution of methanol / acetonitrile (weight ratio: 1: 1), and washed with stirring at 60 ° C. for 5 minutes. This is filtered and dried,
4.1 g of TKXE crystals were obtained. The results obtained are shown in [Table 1].

[0047]

[Table 1]

Comparative Example 1 2,6-xylenol 61 was placed in a 100 ml flask equipped with a stirrer, a temperature controller, a water separator and a dropping funnel.
g, 11.5 g of 40% glyoxal aqueous solution,
At 100 to 105 ° C. and 700 mmHg, 6 g of water in the reaction system was distilled out of the system. When the concentration of water in the reaction system is 1.
At the time when the concentration became 7% by weight, 1.9 g of a 5% p-toluenesulfonic acid aqueous solution was gradually added from a dropping funnel, and the water generated in the condensation reaction was continuously distilled off to reduce the concentration of water in the reaction system to 0. It was kept at 0.9 to 1.9% by weight and reacted at 110 ° C. for 2 hours.

After the reaction, 5.4% aqueous sodium hydroxide solution 5.4
g was added to neutralize. Further, the mixture was heated to 180 ° C. under reduced pressure to distill water, unreacted 2,6-xylenol and the like, to obtain 29 g of a reaction product. (Hereinafter, this reaction product is referred to as polyphenol.) The obtained polyphenol is subjected to high performance liquid chromatography (H
When analyzed using PLC), the content (purity) of TKXE was 51% by weight. As impurities, about 10% by weight of a low molecular weight substance and about 39% by weight of a high-order condensate were contained. Attempts were made to dissolve / recrystallize with tetrahydrofuran / methanol system, but it was difficult to separate impurities. Further, washing with methanol, toluene and acetonitrile did not remove impurities.

Example 14 30 parts by weight of TKXE obtained in the same manner as in Example 1,
Orthocresol novolak type epoxy resin (manufactured by Nippon Kayaku Co., Ltd., EOCN-102S, epoxy equivalent 214,
Softening point 75 ° C) 100 parts by weight and 2-ethyl-4
And 0.5 parts by weight of -methylimidazole were mixed, and the mixture was roll-kneaded at a kneading temperature of 100 to 110 ° C and a kneading time of 5 minutes. After cooling the sheet-like kneaded material, it was pulverized to obtain an epoxy resin composition. Then, 200 kg of the composition
A molded article having a predetermined shape was prepared by compression molding at 170 ° C./cm ^{2 for} 5 minutes, and further heated in an oven at 175 ° C. for 4.5 hours to obtain a cured epoxy resin. The glass transition temperature of the cured product was 192 ° C.

The characteristic values of the cured epoxy resin were evaluated according to the following methods. Glass transition temperature (unit: ° C); From the temperature-linear expansion curve of a molded product measured using a TMA device manufactured by Rigaku Denki, the temperature at the inflection point was taken as the glass transition temperature. The temperature was measured from room temperature to 250 ° C., and the rate of temperature rise was 2 ° C./min.

Comparative Example 2 Example 14 was repeated except that TKXE obtained in the same manner as in Example 1 was replaced with 30 parts by weight of polyphenol obtained in the same manner as in Comparative Example 1. In the same manner as in the above, an epoxy resin cured product was obtained. The glass transition temperature of the cured product was 173 ° C.

Example 15 25.5 g of TKXE obtained in the same manner as in Example 2,
After 255.0 g of epichlorohydrin was mixed and maintained at 100 ° C., 19 g of a 50% by weight aqueous NaOH solution was added dropwise over 3 hours, and the mixture was further aged at 100 ° C. for 2 hours. After neutralization with hydrochloric acid, washing with water was repeated twice. Then, at 50 ° C, 4
Epichlorohydrin was removed at 0 mmHg, and 160
C., dried at 7 mmHg.
8.4 g were obtained. Epoxy equivalent is 263 g / eq. Met.

Next, 100 parts by weight of the obtained epoxy resin, 30 parts by weight of TKXE obtained by the same method as in Example 2, and 0.1 part by weight of 2-ethyl-4-methylimidazole.
5 parts by weight were mixed. Using this mixture, Example 14
In the same manner as in the above, an epoxy resin cured product was obtained. The properties of the obtained cured product were evaluated in the same manner as in Example 14. The glass transition temperature of the cured product was 202 ° C.

Comparative Example 3 The procedure of Example 15 was repeated, except that TKXE obtained by the same method as in Example 2 was replaced by polyphenol obtained by the same method as in Comparative Example 1. Thus, an epoxy resin cured product was obtained. The glass transition temperature of the cured product was 182 ° C.

[0056]

According to the method for producing TKXE of the present invention,
High purity TKXE is obtained as crystals. This method does not generate a large amount of wastewater containing organic matter.

The epoxy resin and epoxy resin composition of the present invention give a cured product having excellent heat resistance, mechanical properties, electrical properties and the like.

[Brief description of the drawings]

FIG. 1 shows an infrared absorption spectrum of TKXE obtained in Example 1.

FIG. 2 shows a nuclear magnetic resonance spectrum of TKXE obtained in Example 1.

[Explanation of symbols]

In FIG. 2, curve A indicates a nuclear magnetic resonance spectrum, and curve B indicates an integral curve of the nuclear magnetic resonance spectrum.

──────────────────────────────────────────────────続 き Continued on the front page (51) Int.Cl. ⁶ Identification symbol FI // C07B 61/00 300 C07B 61/00 300

Claims (2)

[Claims] 1. High purity 1,1,2,2-tetrakis (4) obtained by dehydrocondensation of two molecules of bis (3,5-dimethyl-4-hydroxyphenyl) methane under oxidizing conditions.
-Hydroxy-3,5-dimethylphenyl) ethane (A) and an epoxy resin (B), wherein the amounts of (A) and (B) are (A) per mole of epoxy group of (B)
An epoxy resin composition having a hydroxyl group of 0.5 to 2 mol. 2. High purity 1,1,2,2-tetrakis (4-hydroxy-3) is obtained by dehydrocondensing two molecules of bis (3,5-dimethyl-4-hydroxyphenyl) methane under oxidizing conditions. , 5-Dimethylphenyl) ethane (A), and (A) and the epoxy resin (B) are converted such that the hydroxyl group of (A) is 0.5 to 2 mol per 1 mol of epoxy group of (B). A method for producing an epoxy resin composition, characterized by mixing in an amount.