JP3068285B2 - Epoxy resin, epoxy resin composition and cured product thereof - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an epoxy resin and an epoxy resin composition having excellent heat resistance and water resistance, and a cured product thereof. The composition of the present invention relates to a molding material, a casting material, a laminated material, and a composite material. It is extremely useful for a wide range of applications such as materials, paints, adhesives, and resists.

[0002]

2. Description of the Related Art Epoxy resins can be cured with various curing agents to give cured products having generally excellent mechanical properties, water resistance, chemical resistance, heat resistance, and electrical properties. It is used in a wide range of fields, such as laminates, molding materials, and casting materials.

Conventionally, the most industrially used epoxy resins include liquid and solid bisphenol A epoxy resins obtained by reacting bisphenol A with epichlorohydrin. In addition, a flame-retardant solid epoxy resin obtained by reacting tetrabisphenol A with a liquid bisphenol A-type epoxy resin is used industrially.

[0004]

However, the above-mentioned epoxy resin has a drawback that it has poor water resistance. On the other hand, with recent remarkable developments in the electronics industry and the like, the characteristics required for electrical insulating materials and the like used for them have become increasingly severe, and the emergence of epoxy resins having excellent water resistance has been awaited.

[0005]

In view of these circumstances, the present inventors have conducted intensive studies for an epoxy resin having excellent water resistance. As a result, the general formula (3)

[0006]

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Or the general formula (4)

[0008]

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(Wherein R _{1 to} R ₅ and n have the same meanings as in the following formulas (1) and (2)), wherein an epoxy resin obtained by epoxidizing an alcoholic hydroxyl group of a compound represented by the formula The inventor has found that the present invention has the above-mentioned characteristics, and has completed the present invention. That is, the present invention relates to (1) General formula (1)

[0010]

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Or the general formula (2)

[0012]

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(Wherein R ₁ and R ₂ are the same or different,
Expression (a)

[0014]

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(B)

[0016]

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(C)

[0018]

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Or (d)

[0020]

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Wherein A is alkylene; cycloalkylene; halogen; alkylene substituted with cycloalkyl or aryl;

[0022]

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Or

[0024]

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Wherein X _{1 to} X ₂₆ are each independently a hydrogen atom, an alkyl group or a halogen. R ₃ ~R ₅
Represents an alkyl group; an alkyl group substituted with halogen; an aryl group; an aryl group or cycloalkyl group substituted with alkyl or halogen; a naphthyl group substituted with alkyl or halogen; a biphenyl group substituted with alkyl or halogen. . M is a glycidyl group or a hydrogen atom, and n is an integer of 1 or more. However, at least one M is a glycidyl group. Epoxy resin represented by). (2) An epoxy resin composition comprising an epoxy resin, a curing agent, and, if necessary, a curing accelerator, wherein the epoxy resin composition according to (1) is contained as the epoxy resin component. And (3) a cured product of the epoxy resin composition described in (2), and (4) an epoxy resin composition for a laminate comprising the epoxy resin composition described in (2).

The epoxy resin of the present invention can be prepared by reacting an alcoholic hydroxyl group of a compound represented by the general formula (3) or (4) with epichlorohydrin, for example, by using a quaternary ammonium salt, dimethyl sulfoxide or 1,3-dimethyl-2-amine. It can be obtained by using imidazolidinone in the presence of an alkali metal hydroxide. By adjusting the amount of the alkali metal hydroxide used, the desired amount of the alcoholic hydroxyl group can be epoxidized.
Almost no reaction occurs even when the reaction between the alcoholic hydroxyl group of the compound represented by the general formula (3) or (4) and epichlorohydrin is performed using an excess of epichlorohydrin in the presence of a strong alkali. However, the alcoholic hydroxyl group of the compound represented by the general formula (3) or (4) is more reactive than general alcohols, and is a quaternary ammonium salt, dimethyl sulfoxide, or 1,3-dimethyl-2-imidazolide. When nonone is used, the reaction between the alcoholic hydroxyl group of the compound represented by formula (3) or (4) and epichlorohydrin can be selectively performed. Further, by adjusting the amount of the alkali metal hydroxide, the alcoholic hydroxyl group of the compound represented by the general formula (3) or (4) can be epoxidized to a desired ratio. When the reaction between the alcoholic hydroxyl group represented by the general formula (3) or (4) and epichlorohydrin is carried out in the presence of a Lewis acid catalyst, as in the reaction between general alcohols and epichlorohydrin. The reaction between the alcoholic hydroxyl group of the compound represented by the formula (3) and epichlorohydrin can be performed. However, epichlorohydrin reacts with the hydroxyl group of chlorohydrin as an intermediate product in a large amount, resulting in an extremely high content of hydrolyzable chlorine and a low epoxy content, which is not preferable. On the other hand, general formula (4)
When the reaction between the hydroxyl group of the compound represented by the formula and epichlorohydrin is carried out in the presence of an acid catalyst, the reaction between the epoxy group and the alcoholic hydroxyl group of the compound represented by the general formula (4) occurs simultaneously, so the formula of the present invention It is difficult to obtain an epoxy resin in which only the alcoholic hydroxyl group of the compound represented by (4) is epoxidized.

Hereinafter, the present invention will be described in detail. Examples of the epoxy resin represented by the general formula (1) or (2) of the present invention include, for example, those in which R ₁ and R ₂ in the general formula (1) or (2) are represented by the above-mentioned formula (a). For example

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[0029]

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[0032]

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[0034]

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[0035]

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[0036]

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[0037]

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[0039]

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[0040]

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[0041]

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[0042]

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[0043]

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[0044]

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As the one represented by (b), for example,

[0046]

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[0047]

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As the one represented by (c), for example,

[0049]

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[0050]

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[0051]

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[0052]

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[0053]

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[0059]

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[0060]

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[0061]

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[0064]

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[0065]

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[0066]

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[0067]

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As the one represented by (d), for example,

[0069]

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[0070]

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The following are examples, but the present invention is not limited to these. Further, R ₁ and R ₂ in the general formula (1) or (2) may include different ones.

Or R ₃ and R ₄ and R ₅ include, for example,

[0073]

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[0074]

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[0075]

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[0076]

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[0077]

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[0078]

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[0085]

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[0086]

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The following are examples, but the present invention is not limited to these. Further, R _3, R ₄ and R ₅ in the general formula (1) or (2) may include different ones. The epoxy resin of the present invention has the general formula (1)
Alternatively, in the general formula (2), n is 1 or more in the general formula (1) or (2), and n is preferably 1 to 13, particularly preferably 1 to 6. When n is less than 1, the toughness of a cured product obtained by using n is insufficient, which is not preferable. On the other hand, if n exceeds 13, the softening point and the melt viscosity of the epoxy resin are high, and handling becomes difficult, which is not preferred. Further, R ₁ and R ₂ in the general formula (1) or the general formula (2) represent the above formula (C-2), the formula (C-1) or a mixture of the formula (C-2) and the formula (C-1). Particularly preferred. Epoxy wherein R ₁ and R ₂ in the general formula (1) or the general formula (2) are the formula (c-2) or the formula (c-1) or a mixture of the formula (c-2) and the formula (c-1) Resins are particularly preferable because the heat resistance of the cured product obtained by using them is very excellent. Further, R ₃ , R ₄ and R ₅ in the general formula (1) or the general formula (2) represent
8), Equation (E-9), Equation (E-12), Equation (E-7),
Formula (e-3) or formula (e-4) is particularly preferred. R ₃ , R ₄ and R _{5 in the} general formula (1) or the general formula (2)
Is an epoxy resin represented by the formula (e-8), the formula (e-9), the formula (e-12), the formula (e-7), the formula (e-3) or the formula (e-4). The cured product obtained by this method is excellent in heat resistance and is particularly preferable. The reaction between the alcoholic hydroxyl group of the compound represented by the general formula (3) or (4) and epichlorohydrin is carried out in the presence of an alkali metal hydroxide in the presence of dimethyl sulfoxide or a quaternary ammonium salt or 1,3-
This can be done by using dimethyl-3-imidazolidinone. At that time, alcohols, aromatic hydrocarbons, ketones, cyclic and ether compounds, etc. may be used in combination as a solvent. Dimethyl sulfoxide, 4
A quaternary ammonium salt and 1,3-dimethyl-2-imidazolidinone may be used in combination.

If dimethyl sulfoxide, a quaternary ammonium salt or 1,3-dimethyl-2-imidazolidinone is not used, the reaction does not proceed sufficiently and a large amount of alkali metal hydroxide remains, resulting in polymerization. It is difficult to produce the epoxy resin of the present invention.

The amount of dimethyl sulfoxide used is 5% by weight based on the compound represented by formula (3) or (4).
~ 300% by weight is preferred. General formula (3) or (4)
When the amount is 5% by weight or less with respect to the compound represented by the formula, the reaction between the alcoholic hydroxyl group of the compound represented by the general formula (3) or (4) and epichlorohydrin becomes slow, so that a long-time reaction is required, and thus it is preferable Absent. If the amount exceeds 300% by weight based on the compound represented by the general formula (3) or (4), the effect of increasing the amount is almost negligible, but the volumetric efficiency deteriorates, which is not preferable.

Examples of the quaternary ammonium salt include tetramethylammonium chloride, tetramethylammonium bromide and trimethylbenzylammonium chloride, and the amount is preferably 0.3 to 50 g per equivalent of the alcoholic hydroxyl group to be epoxidized. If the amount is less than 0.3 g with respect to 1 equivalent of the alcoholic hydroxyl group to be epoxidized, the reaction between the alcoholic hydroxyl group of the compound represented by the general formula (3) or (4) and epichlorohydrin is slowed down, and the reaction for a long time is delayed. It is necessary and not preferable. If it exceeds 50 g with respect to 1 equivalent of the alcoholic hydroxyl group, the effect of increasing the amount is almost lost, but the cost increases, which is not preferable.

The amount of epichlorohydrin used may be at least equivalent to one equivalent of the alcoholic hydroxyl group to be epoxidized of the compound represented by formula (3) or (4). However, if it exceeds 30 equivalents to 1 equivalent of the alcoholic hydroxyl group to be epoxidized, the effect of increasing the amount is almost negligible, but the volumetric efficiency deteriorates, which is not preferable.

As the alkali metal hydroxide, caustic soda, caustic potash, lithium hydroxide, calcium hydroxide and the like can be used, but caustic soda is preferred. The amount of the alkali metal hydroxide used may be approximately equivalent to 1 equivalent of the alcoholic hydroxyl group to be epoxidized of the compound represented by the general formula (3) or (4). When the alcoholic hydroxyl group of the compound represented by the general formula (3) or (4) is completely epoxidized, it may be used in excess, but if it exceeds 2 equivalents to 1 equivalent of the alcoholic hydroxyl group, it may be slightly used. Polymerization tends to occur. The alkali metal hydroxide may be a solid or an aqueous solution. When an aqueous solution is used, the reaction can be carried out while distilling water out of the reaction system under normal pressure and reduced pressure during the reaction.

The reaction temperature is preferably from 30 to 100 ° C. When the reaction temperature is lower than 30 ° C., the reaction becomes slow and a long-time reaction is required. If the reaction temperature exceeds 100 ° C., many side reactions occur, which is not preferable.

After completion of the reaction, excess epichlorohydrin and solvents are recovered by distillation under reduced pressure, and then the resin is dissolved in an organic solvent to remove residual chlorine with an alkali metal hydroxide. On the other hand, after completion of the reaction, by-separation with water to separate by-product salts and solvents, and distilling off excess epichlorohydrin from the oil layer under reduced pressure, dissolve the resin in an organic solvent and remove chlorine remaining in the alkali metal hydroxide. Removal may be performed. As organic solvents, methyl isobutyl ketone,
Benzene, toluene, xylene and the like can be used, but methyl isobutyl ketone is preferred. They can be used alone or in a mixed system.

The epoxy resin of the present invention can be cured alone or in combination with other epoxy resins by adding a curing agent and, if necessary, a curing accelerator as in the case of ordinary epoxy resins.

The curing agent which can be used in the present invention includes amine compounds, acid anhydride compounds, amide compounds, phenol compounds and the like. Specific examples include diaminodiphenylmethane, diethylenetriamine, triethylenetetramine, diaminodiphenylsulfone, isophoronediamine, dicyansamide, a polyamide resin synthesized from a dimer of linolenic acid and ethylenediamine, phthalic anhydride, trimellitic anhydride, and pyromethylene anhydride. Melitic acid, maleic anhydride, tetrahydrophthalic anhydride, methyltetrahydrophthalic anhydride, methylnadic anhydride, hexahydrophthalic anhydride, methylhexahydrophthalic anhydride,
Phenol novolak, and modified products thereof, and the like. These curing agents may be used alone or in combination of two or more.

The amount of the curing agent used is preferably 0.7 to 1.2 equivalents to the epoxy group. If the amount is less than 0.7 equivalents or more than 1.2 equivalents with respect to the epoxy group, curing may be incomplete and good cured physical properties may not be obtained. The epoxy resin of the present invention may be cured using a curing accelerator. Examples of the curing accelerator include imidazoles, tertiary amines, phenols, Lewis acid salts such as boron trifluoride-monoethylamine complex, and the like. Various additives such as an inorganic or organic filler can be added as needed.

The amount of these curing accelerators used is preferably 0.1 to 5.0 parts by weight based on 100 parts by weight of the epoxy resin.

The epoxy resin composition of the present invention containing the epoxy resin of the present invention, a curing agent and, if necessary, a curing accelerator can be easily prepared by a method similar to a conventionally known method. Obtainable. For example, an epoxy resin composition is obtained by sufficiently mixing the epoxy resin of the present invention with a curing agent, a filler, and other additives using an extruder, a kneader, a roll, or the like, as necessary, until the mixture becomes uniform. Can be. Further, after the epoxy resin composition is melted, molded using a casting or transfer molding machine or the like, and further heated to 80 to 200 ° C., a cured product can be obtained.

A prepreg obtained by dissolving the epoxy resin composition of the present invention in a solvent, impregnating a base material such as glass fiber, carbon fiber, polyester fiber, polyamide fiber, alumina fiber, paper or the like and drying by heating is subjected to hot pressing. It is also possible to obtain a cured product by molding.

[0101]

EXAMPLES Next, the present invention will be described in detail with reference to Examples, Application Examples and Application Comparative Examples. Hereinafter, all parts are by weight unless otherwise specified. The hydrolyzable chlorine content is determined by dissolving an epoxy resin in dioxane, adding an ethanol solution of 1N-potassium hydroxide, and heating the solution at reflux for 30 minutes to titrate chloride ions released by titration with a silver nitrate solution. , The weight of chlorine atoms in the compound expressed as a percentage by weight.

Example 1 In the general formula (3), R ₁ and R ₂ are the same as those of the formula (C)
427 parts of a compound (a) which is a mixture of 1) and the above formula (c-2), wherein R ₃ and R ₄ are the above formula (e-8), and the average value of n is 1.5. Is dissolved in 925 parts (10 equivalents) of epichlorohydrin and 462.5 parts of dimethylsulfoxide, and then 52.8 parts (1.3 equivalents) of 98.5% NaOH at 70 ° C. with stirring.
Was added over 100 minutes. After the addition, the reaction was further performed at 70 ° C. for 3 hours. Then, most of the excess unreacted epichlorohydrin and dimethyl sulfoxide are recovered by distillation under reduced pressure, the reaction product containing the by-product salt and dimethyl sulfoxide is dissolved in 750 g of methyl isobutyl ketone, and 10 parts of 30% NaOH (0.075 equivalent). 70 ° C
For 1 hour. After the completion of the reaction, the resultant was washed twice with 200 parts of water. After oil-water separation, methylisoble ketone was distilled and recovered from the oil layer, and the epoxy equivalent was 449, the content of hydrolyzable chlorine was 0.046%, the softening point was 64.8 ° C, the melt viscosity (150 ° C) was 3.0 poise, and the bromine was bromine. 453 parts of an epoxy resin (a) having a content of 31.6% were obtained. When the obtained epoxy resin (a) is calculated from the epoxy equivalent, almost 3.5 of the alcoholic hydroxyl groups in the general formula (2) are epoxidized.

Example 2 Instead of the compound (a), R ₁ and R ₂ in the general formula (4) are a mixture of the above formulas (c-1) and (c-2), and R ₅ is An epoxy equivalent of 391 and a hydrolyzable chlorine content of 0.045 were obtained in the same manner as in Example 1 except that 503 parts of the compound (b) having the formula (e-8) and having an average value of n of 1.5 was used. %, A softening point of 64.5 ° C., a melt viscosity (150 ° C.) of 2.9 poise, and 529 parts of an epoxy resin (b) having a bromine content of 26.7%. When the obtained epoxy resin (b) is calculated from the epoxy equivalent, almost 2.5 of the alcoholic hydroxyl groups in the general formula (4) are epoxidized.

Example 3 Instead of the compound (a), R ₁ and R ₂ in the general formula (4) are a mixture of the above formulas (c-1) and (c-2), and R ₅ is 98. Using 503 parts of the compound (b) having the formula (e-8), wherein the average value of n is 1.5, using 5 parts of tetramethylammonium chloride instead of 462.5 parts of dimethyl sulfoxide; 5% NaOH
An epoxy equivalent of 58 was obtained in the same manner as in Example 1 except that 28.4 parts of 98.5% NaOH was used instead of 52.8 parts.
9. Hydrolyzable chlorine content 0.045%, softening point
500 parts of an epoxy resin (c) having 4 ° C., a melt viscosity (150 ° C.) of 6.7 poise and a bromine content of 28.2% was obtained. When the obtained epoxy resin (c) is calculated from the epoxy equivalent, about 1.2 of 2.5 alcoholic hydroxyl groups in the general formula (4) are epoxidized.

Example 4 Instead of the compound (a), R ₁ and R ₂ in the general formula (3) are the same as the formula (C-1), and R ₃ and R ₄ are the same as the formula (E-8). , N was 2.2, and an epoxy equivalent of 409 and a hydrolyzable chlorine content of 0.0 were used in the same manner as in Example 1 except that 350 parts of the compound (c) having an average value of 2.2 was used.
78%, softening point 66.2 ° C, melt viscosity (150 ° C) 4.
Epoxy resin with 2 poises and bromine content of 18.8% (d)
358 parts were obtained. Calculated from the epoxy equivalent, the obtained epoxy resin (d) is almost epoxidized with 4.2 alcoholic hydroxyl groups in the general formula (3).

Example 5 Instead of the compound (a), R ₁ and R ₂ in the general formula (3) are the same as the formula (C-1), and R ₃ and R ₄ are the same as the formula (E-3). , N was 3.3, and an epoxy equivalent of 374 and a hydrolyzable chlorine content of 0.0 were used in the same manner as in Example 1 except that 284 parts of the compound (d) having an average value of 3.3 was used.
631 parts of an epoxy resin (e) having 52%, a softening point of 60 ° C. and a melt viscosity (150 ° C.) of 5.2 poise were obtained. When the obtained epoxy resin (e) is calculated from the epoxy equivalent, 4.7 of the 5.3 alcoholic hydroxyl groups in the general formula (2) are obtained.
The pieces are epoxidized. Epoxy resins (a) to (e) obtained in Examples 1 to 5, for comparison, general formula (5)

[0107]

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R ₆ and R ₇ in the formula (C)
A mixture of 1) and the above formula (c-2), the average value of n is 1.5, the softening point is 70.7 ° C, and the bromine content is 21.
1% of the epoxy resin (f) and R ₆ and R ₇ in the general formula (5) are the above formula (c-1), the average value of n is 2.2, and the epoxy resin having a softening point of 67.0 ° C. Table 1 shows the physical properties of the resin (g).

Application Examples 1 to 5 and Application Comparative Examples 1 to 2 Epoxy resins (a) to (e) obtained in Examples 1 to 5, and epoxy resins (f) to
(G), Kayahard MCD (manufactured by Nippon Kayaku Co., Ltd., methylendmethylenetetrahydrophthalic anhydride) as a curing agent, and 2E4MZ (2-ethyl-
4-methylimidazole) and the composition shown in Table 1 (the numerical values indicate parts by weight) so that the number of acid anhydride groups is 0.9 per epoxy group of the epoxy resin. These were cured at 100 ° C. for 2 hours, then at 120 ° C. for 2 hours, and further at 200 ° C. for 5 hours to obtain test specimens.
Heat deformation temperature, flexural strength, and JISK-6911
The flexural modulus and the water absorption were measured. Table 1 shows the results.

The epoxy resins (a) to (e) obtained in Examples 1 to 5 and the epoxy resins (f) to (g) for comparison were dissolved in methyl ethyl ketone to obtain a solution having a resin concentration of 80% by weight. Was prepared. These epoxy resin solutions were mixed with dicyandiamide as a curing agent, benzyldimethylamine as a curing accelerator, methylcellosolve and dimethylformamide as solvents in the composition shown in Table 2 (numerical values indicate parts by weight) to form a varnish-like epoxy resin composition. Was prepared. This composition is impregnated in a glass cloth (WE-18K-BZ2, manufactured by Nitto Boseki Co., Ltd.), and is impregnated at 110 ° C.
For 30 minutes to obtain a B-staged prepreg,
9 ply of this prepreg, 170 ° C, 40kgf / cm
^2. A glass cloth laminate having a thickness of 1.5 mm was formed under the forming conditions for 45 minutes, and the glass transition temperature, the measling resistance, and the water absorption were measured in accordance with JIS C-6481. Table 2 shows the results.

Table 1 (1) Example 1 2 3 4 5 Epoxy resin (a) 100 Epoxy resin (b) 100 Epoxy resin (c) 100 Epoxy resin (d) 100 Epoxy resin (e) 100 Epoxy resin (f) ) Epoxy resin (g) Tree Epoxy equivalent (g / eq) 449 391 589 409 374 Fat Hydrolysable chlorine content (%) 0.046 0.045 0.045 0.078 0.052 Softening point (℃) 64.8 64.5 77.4 66.2 60.0 Melt viscosity ( 150 ° C, ps) 3.0 2.9 6.7 4.2 5.2 Bromine content (%) 31.6 26.7 28.2 18.8-Kayahard MCD 35.7 41.0 27.2 39.2 42.8 combined 2E4MZ 1 1 1 1 1 Hard heat deformation temperature (° C) 137 148 135 139 132 Strength (kg / mm ² ) 14.8 12.9 12.9 12.2 12.2 Object Flexural modulus (kg / mm ² ) 360 330 330 330 283 Properties Water absorption (boiling / 20hr,%) 0.92 0.87 0.97 0.96 1.25

[0112]

Table 2 (1) Example 1 2 3 4 5 Epoxy resin (a) 80 epoxy resin (b) 80 epoxy resin (c) epoxy resin (d) 80 80 epoxy resin (e) 80 epoxy resin (F) Epoxy resin (g) Dicyandiamide 3.4 3.4 3.4 3.4 3.4 Table 2 (1) continued Example 1 2 3 4 5 Benzyl dimethylamine 0.08 0.08 0.08 0.08 0.08 Methyl ethyl ketone 20 20 20 20 20 Methyl cellosolve 21 21 21 21 21 Dimethyl Formamide 21 21 21 21 21 Hard glass transition temperature (° C) 128 136 128 130 127 Anti-measuring properties * ○ ○ ○ ○ ○ Properties Water absorption (boiling / 20hr) 0.18 0.18 0.25 0.20 0.19 * Abnormal appearance after immersion in solder for 20 seconds

[0114] * 1 hour after boiling, no abnormal appearance after immersion in 260 ° C solder for 20 seconds

As is clear from Tables 1 and 2, the epoxy resin of the present invention has a higher water resistance and a higher heat resistance than the conventional epoxy resin. Are equal to or greater than.

[0116]

The epoxy resin of the present invention can give a cured product excellent in heat resistance and water resistance, and can be used in a wide range of molding materials, casting materials, laminated materials, composite materials, paints, adhesives, resists and the like. Very useful for applications.

──────────────────────────────────────────────────続 き Continuation of the front page (56) References JP-A-60-31517 (JP, A) JP-A-62-197415 (JP, A) JP-A-1-168722 (JP, A) JP-A-2- 248743 (JP, A) JP-A-3-156045 (JP, A) JP-A-3-255934 (JP, A) (58) Fields investigated (Int. Cl. ⁷ , DB name) C08G 59/04 C08G 59 / 14 C08G 59/20-59/38 C07D 301/28 C07D 303/27

Claims (4)

(57) [Claims] 1. A compound of the general formula (1) Or the general formula (2) (Wherein R ₁ and R ₂ are the same or different and have the formula (A) (B) (C) Or (d) A is alkylene; cycloalkylene; halogen; alkylene substituted with cycloalkyl or aryl; Or And X _{1 to} X ₂₆ are each independently a hydrogen atom, an alkyl group or a halogen. R _{3 to} R ₅ are an alkyl group; an alkyl group substituted with halogen; an aryl group; an aryl group or cycloalkyl group substituted with alkyl or halogen; a naphthyl group substituted with alkyl or halogen; Represents a biphenyl group. M is a glycidyl group or a hydrogen atom, and n is an integer of 1 or more. Where M is at least 1
Are glycidyl groups. Epoxy resin represented by). 2. An epoxy resin composition comprising an epoxy resin, a curing agent and, if necessary, a curing accelerator, wherein the epoxy resin according to claim 1 is contained as said epoxy resin component. Composition. 3. A cured product of the epoxy resin composition according to claim 2. 4. An epoxy resin composition for a laminate comprising the epoxy resin composition according to claim 2.