JPH01275623A - Epoxy resin composition and its cured product - Google Patents

Abstract

PURPOSE:To obtain an epoxy resin composition which gives a cured product improved in bending strength, bending elongation, Izod strength, etc., without lowering its heat resistance, by mixing an epoxy resin composition comprising an epoxy resin and a curing agent with a specified glycidyl compound. CONSTITUTION:An epoxy resin composition is produced by mixing a glycidyl compound of formula I (wherein R<1> is a 1-20C monovalent hydrocarbon group, R<2> is a 1-6C bivalent hydrocarbon group, R<3> is a 1-6C monovalent hydrocarbon group, n is 0-50, and X is H or glycidyl), e.g., formula II, with an epoxy resin (e.g., epi-bis epoxy resin) and an epoxy resin curing agent (e.g., 3,4'- diaminodiphenylmethane) as essential components. The obtained epoxy resin composition can be desirably used as, e.g., a matrix of an aircraft prepreg. The compound of formula I can be produced by using an amine-modified silicone of formula III as a starting material.

Description

DETAILED DESCRIPTION OF THE INVENTION [Field of Industrial Application] The present invention relates to an epoxy resin composition that provides a cured product with high heat resistance and excellent toughness, and a cured product obtained by curing the same.

[Prior art/issues to be solved by the invention] Epoxy resins are used in many fields such as adhesives, paints, coatings, materials for electrical equipment, materials for civil engineering and construction, and matrix materials for PRP. ing. Especially N, N-
Epoxy resins having at least one diglycidylamino group in one molecule (hereinafter also referred to as glycidylamine-based epoxy resins) and epoxy resins obtained by the condensation reaction of bisphenols and shrimp halohydrin (hereinafter referred to as epi-bis type epoxy resins) The cured product obtained by heat curing with a curing agent has both high heat resistance and excellent adhesion to substrates, so it is used as a matrix for heat-resistant adhesives and prepregs for space and aviation applications. There is.

However, since cured epoxy resins generally do not have sufficient flexibility or toughness, it cannot be said that they sufficiently meet the mechanical properties required for various uses.

Therefore, many attempts have been made to add flexibility imparting agents to ordinary epoxy resin compositions to improve various mechanical properties such as elongation. One of the known methods is to use a reactive diluent such as diglycidyl ether of polypropylene glycol or diglycidyl ether of polyethylene glycol. Otherwise, there is a disadvantage that a sufficient modification effect cannot be obtained and the heat resistance of the cured product is greatly reduced.

Therefore, various rubber modifiers such as carboxyl-terminated butadiene-acrylonitrile rubber (CTBN) and amino-terminated butadiene-acrylonitrile rubber (ATBN) are used to suppress the decrease in heat resistance by giving the cured product a sea-island structure. A method has also been devised (published by Shokodo,
(See "New Epoxy Resins" edited by Hiroshi Kakiuchi, etc.). However, these rubber-based modifiers are very susceptible to oxidation and easily deteriorate, resulting in a disadvantage that the long-term heat resistance of the cured product decreases.

In addition, a method has been proposed in which silicone rubber that is stable against oxidation is blended with epoxy resin and dispersed microscopically (Japanese Unexamined Patent Publication No. 58-21417), but essentially (
Poly)siloxane has poor compatibility with epoxy resins,
It is known that there is a drawback that it bleeds onto the surface due to thermal history (Japanese Patent Application Laid-Open No. 82-118854).

[Means for Solving the Problems] In view of the above circumstances, the present inventors have conducted intensive research on a method of imparting toughness to a cured epoxy resin without significantly reducing its heat resistance. It was discovered that a composition containing a glycidyl compound having a poly)siloxane skeleton satisfies this purpose, and the present invention was achieved.

That is, the present invention provides: (2) General formula (I): (wherein, R1 is a monovalent hydrocarbon group having 1 to 20 carbon atoms, R
2 is a divalent hydrocarbon group having 1 to 6 carbon atoms, R3 is a carbon number 1
~6 monovalent hydrocarbon group, n is an integer of θ ~ 50, X represents a hydrogen atom or a glycidyl group) Contains (B) an epoxy resin and (C) an epoxy resin curing agent The present invention relates to an epoxy resin composition and a cured product obtained by curing the resin composition.

[Example] The resin composition of the present invention has the general formula (I)=(wherein, R1
is a monovalent hydrocarbon group having 1 to 2 carbon atoms, and R2 is a monovalent hydrocarbon group having 1 to 2 carbon atoms.
~6 divalent hydrocarbon group, R3 is a monovalent hydrocarbon group having 1 to 6 carbon atoms, n is an integer of 0 to 50, and X represents a hydrogen atom or a glycidyl group), as the main chain It contains a glycidyl compound (hereinafter also referred to as a glycidyl compound) having a (poly)siloxane skeleton. Since glycidyl compounds have glycidyl groups in their molecules, they can be cured using the same curing agent as epoxy resins and are incorporated into the curing system. As it hardens, it takes on a microscopic phase-separated structure, but because it is chemically bonded, it rarely bleeds.

In general formula (1), R1 is a monovalent hydrocarbon group having 1 to 20 carbon atoms, and specific examples include methyl group, ethyl group, n
- Aliphatic hydrocarbon groups such as propyl group and inpropyl group, aromatic hydrocarbon groups such as phenyl group, tolyl group, dimethylphenyl group, naphthyl group, O-1+11- or p-cumenyl group, and mesityl group. It will be done. Among these, R1 is preferably a methyl group, ethyl group, phenyl group, tolyl group, dimethylphenyl group, naphthyl group, etc., because the raw materials are easily available. In particular, aromatic hydrocarbon groups such as phenyl group, tolyl group, dimethylphenyl group, and naphthyl group are preferred from the viewpoint of easy industrial availability of raw materials.

When R1 is a monovalent hydrocarbon group having more than 20 carbon atoms, it is difficult to obtain raw materials.

In the general formula (I), R2 is a divalent hydrocarbon group having 1 to 6 carbon atoms, and specific examples include a methylene group, an ethylene group,
Examples include trimethylene group and tetramethylene group.

Among these, those in which R2 is a trimethylene group are preferred because they are easily available.

In general formula (I), R3 is a monovalent hydrocarbon group having 1 to 6 carbon atoms, and specific examples include methyl group, ethyl group, phenyl group, etc., and raw materials for these are easily available. This is particularly desirable.

In the general formula [1), n is an integer from θ to 5o, and an integer from 4 to 45 is preferred because it facilitates the formation of an appropriate phase-separated structure.If fl exceeds 50, epoxy Since it phase-separates completely from the resin, it becomes extremely difficult to disperse it uniformly.

In the general formula [1), X is a hydrogen atom or a glycidyl group, and the glycidyl compound represented by the general formula ()) is usually obtained as a mixture thereof.

If the ratio of N-H of sulfonamide converted to glycidyl group is the epoxidation rate, the epoxidation rate is 70% or more,
Furthermore, it is preferably 80% or more. Those with a low epoxidation rate have poor storage stability during storage and tend to thicken.

In the general formula m, R1 and R2 each exist two times in one molecule, but they may be the same or different. In general formula (1), 21+4 R3s exist in one molecule, and they may be the same or different.

Examples of glycidyl compounds represented by the general formula (1) include compounds represented by the general formula: (wherein, R2, R3, and nSX are the same as above), and compounds represented by the general formula: (wherein, R2, Examples include compounds represented by the general formula: (wherein R1, R3 and nsX are the same as above). More specific examples of these compounds include glycidyl compounds represented by formula (1): % formula % formula (f): n 5-20.

Among them, the glycidyl compound represented by the formula ai) and the glycidyl compound represented by the formula 0 are preferred because their raw materials are easily available.

Furthermore, the resin composition of the present invention may contain two or more types of glycidyl compounds represented by general formula (1).

The glycidyl compound represented by the general formula m as described above is
It exhibits the properties of a colorless to pale yellowish brown liquid with a low viscosity (about 1 to 50 P) at room temperature.

Such a glycidyl compound represented by the general formula (I) can be produced, for example, by the method described in Japanese Patent Application No. 181505/1982.

That is, first, as the first step, the general formula (■) forming the main chain portion of the glycidyl compound represented by the general formula (I) used in the present invention is: (wherein R2, R3, and n are the same as above). The amine-modified silicone shown has general formula (II); R' 802
A sulfone having a (poly)siloxane skeleton in the main chain is produced by condensing a sulfonyl chloride represented by C1[) (wherein R1 is the same as above) in the presence of an appropriate dehydrochlorination agent such as sodium hydroxide. An amide compound is obtained.

Specific examples of the amine-modified silicone represented by the general formula (1) include 1,3-bis(4-aminobutyl)tetramethyldisiloxane, l.

In addition to 3-bis(4-aminopropyl)tetramethyldisiloxane, there are also silicone oligomers modified with amines at both ends, sold under the trademark 5ILAPLANE J by Chisso ■.
Preferably used. Further, the amine-modified silicone represented by the general formula (II) may be used alone or in a mixture of any plurality thereof.

On the other hand, specific examples of the sulfonyl chloride represented by the general formula (2) include aliphatic sulfonyl chloride such as methanesulfonyl chloride and ethanesulfonyl chloride; benzenesulfonyl chloride, 0- or p-toluenesulfonyl chloride, 2,4 - or 2,5-dimethylbenzenesulfonyl chloride, ■
Examples include aromatic sulfonyl chlorides such as - or 2-naphthalenesulfonyl chloride, and aromatic sulfonyl chlorides are easily available industrially. Also,
The sulfonyl chloride represented by the general formula (110) may be used alone or in combination of any plurality thereof.

In the subsequent second step, the sulfonamide compound obtained in the first step that has a siloxane skeleton in its main chain is subjected to an addition reaction with epihalohydrin, and then a dehydrohalogenation reaction is performed using a caustic alkali such as sodium hydroxide. As a result, a glycidyl compound represented by the general formula (I) is obtained.

The resin composition of the present invention contains an epoxy resin and an epoxy resin curing agent in addition to the glycidyl compound represented by general formula (I).

The epoxy resin (hereinafter also referred to as epoxy resin (B)) is a resin containing at least two epoxy groups in the molecule, and preferably has an epoxy equivalent of 100 to 700 g.
/ equivalent. Specific examples of such epoxy resins include glycidyl obtained from amines such as 4,4'- or 3,4'-diaminodiphenylmethane, de- or p-aminophenol, aminonaphthol, and -xylylene diamine. Amine-based epoxy resin (
For example, YH-434 manufactured by Tobu Kasei ■, Sumitomo Chemical ■
(commercially available as ELM-120, etc. manufactured by Yuka Shell Epoxy Corporation); epi-bis epoxy resins (commercially available, such as Epicoat 807.828.1001, manufactured by Yuka Shell Epoxy); nuclear brominated epi-bis epoxy resins (such as ELM-120, manufactured by Yuka Shell Epoxy); Novolac-type epoxy resins such as glycidylated phenol novolak, glycidylated cresol novolak (commercially available as YDB-400, etc. manufactured by Kasei ■), glycidylated products of phenol novolak (commercially available as EOCN-102, etc. manufactured by Nippon Kayaku ■)
, polyglycidyl ether type epoxy resins represented by nuclear brominated novolak type epoxy resins; polyglycidyl esters such as phthalic acid and cyclohexanedicarboxylic acid; heterocyclic epoxy resins such as hydantoin type epoxy resins and triglycidyl isocyanurate. ; Examples include cycloaliphatic epoxy resins. The epoxy resins may be used alone or in combination of two or more.

Among these epoxy resins, epi-bis type epoxy resins are preferred because of their good balance of various properties, and glycidylamine type epoxy resins are preferred because of their high heat resistance. In particular, the epoxy resin (B) is an epoxy resin having at least one N,N-diglycidylamino group in one molecule, such as tetraglycidyldiaminodiphenylmethane and/or its condensation product. The disadvantage that the cured product is too hard and brittle can be greatly improved by adding the compound represented by the general formula m, which is preferable.

When using the glycidyl compound diagram and the epoxy resin (B) in combination, there is no particular restriction on the ratio of use, but the weight ratio of the glycidyl compound (A)/epoxy resin (B) is preferably 0.01/99.99. It may be arbitrarily selected in the range of ~50/50 depending on the application, but it is more preferably in the range of O,L/99.9 to 20/80.

The epoxy resin curing agent (hereinafter also referred to as curing agent (Q))
may be used without particular limitation as long as it is commonly used. Specific examples include chain aliphatic polyamines such as diethylenetriamine and triethylenetetramine; cyclic aliphatic amines such as menzendiamine and isophoronediamine; and alicyclic polyamines such as p-xylylenediamine. class; enteric- or p-phenylenediamine, 4,4°-diaminodiphenylmethane,
4. Aromatic polyamines such as 4'-diaminodiphenylsulfone; benzyldimethylamine, 2.4. fi-
Tertiary amines such as tris(dimethylaminomethyl)phenol; polyamides; tetrahydrophthalic anhydride, methyltetrahydrophthalic anhydride, hexahydrophthalic anhydride, methylhexahydrophthalic anhydride, methylnadic anhydride, pyromellitic anhydride Acid anhydrides such as , trimellitic anhydride, and benzophenone tetracarboxylic anhydride; imidazoles such as 2-methylimidazole and 2-ethyl-4-methylimidazole; Lewis acids typified by boron trifluoride-amine complexes; -Amine complexes; dicyandiamide and its derivatives; polyphenols such as cresol novolak, phenol novolak, polyvinylphenol, and phenol-formalin initial condensate; polymercaptans, and the like.

Among these are 4,4°- or 3,4°-diaminodiphenylsulfone or 4,4°- or 3.4
Aromatic polyamines having at least two primary amino groups in the molecule, such as °-diaminodiphenylmethane, are preferable because the resulting cured product has excellent heat resistance, and aliphatic amine-based curing An acid anhydride curing agent is preferred because it cures quickly and can be cured even at low temperatures, and an acid anhydride curing agent is preferred because the resulting cured product has excellent heat resistance and electrical properties.

Although the amount of the curing agent [Q to be used differs depending on the type of curing agent, it is usually preferable to use it in an amount ratio known as the optimum usage amount of each curing agent. For example, alicyclic (poly)amine curing agents, aromatic polyamine curing agents,
When using polyphenols, it is preferable to use 0.8 to 1.2 equivalents per equivalent of the total amount of epoxy groups in both the glycidyl compound (5) and the epoxy resin [B), and 0.8 to 1.2 equivalents are used. It is more preferable to use 9 to 1.1 equivalents. In addition, when using an acid anhydride curing agent, it is preferable to use 0.7 to 1.0 equivalent based on the total equivalent of epoxy groups in both the glycidyl compound diagram and the epoxy resin (B), It is more preferable to use 0.8 to 0, g equivalent. Furthermore, when using tertiary amines, imidazoles, Lewis-amine complexes, dicyandiamide, etc., the amount is in the range of 1 to 10 parts based on 100 parts of the total amount of glycidyl compound diagram and epoxy resin (B). Just select the usage amount. By using such a proportion, a cured product having good properties can be obtained.

The resin composition of the present invention includes, if necessary, a curing accelerator, thermosetting resin monomers and thermosetting resins other than epoxy resins, and glass fibers used to blend within a range that does not impair the properties of the composition. , reinforcing agents such as carbon fiber and aramid fiber; fillers such as silica and talc; additives such as coupling agents; pigments; and flame retardants.

Examples of the curing accelerator include tertiary amines such as penzyldimethylamine and 2,4,6-tris(dimethylaminomethyl)phenol, and imidazoles.

The thermosetting resin other than the thermosetting resin monomer and epoxy resin is preferably one that can be cured simultaneously with the composition of the present invention, and examples of the thermosetting resin that can be simultaneously cured include unsaturated polyester resin, vinyl monomer, etc. can be given.

The resin composition of the present invention is usually prepared by mixing together a glycidyl compound, an epoxy resin (B), a curing agent (0), and other components used if necessary. In difficult cases, the composition may be prepared by first dissolving it in an inert solvent, mixing it, and removing the solvent.

In addition, in order to improve the uniformity of the cured product, a glycidyl compound (
2) and the curing agent [C) may be reacted in advance to prepare an adduct, and the epoxy resin (B) may be added to the adduct to prepare the composition.

The composition prepared in this way is cured even at room temperature, but in order to obtain a cured product with excellent heat resistance, it is necessary to
It is preferable to heat at a temperature of 0 to 200°C for 1 to 5 hours. The cured product obtained in this way has an additional 150 to 2
The heat resistance can be further improved by post-curing at a temperature of 50°C.

The cured product is usually cloudy and the (poly)siloxane portion has a phase-separated structure.

The epoxy resin composition of the present invention contains as a component a glycidyl compound cut having a (poly)siloxane skeleton in the main chain,
After curing, this rubber component forms a "sea-island" structure, resulting in greatly improved toughness compared to general cured epoxy resins.

When using a normal flexibility imparting agent, it must be used in an amount of about 10 to 20 parts in 100 parts of the total amount with the epoxy resin, and in exchange for flexibility, the heat resistance of the cured product is Sexuality decreases. However, in the epoxy resin composition of the present invention, even if the glycidyl compound cut is used in the same amount or more than the conventional flexibility imparting agent, the decrease in heat resistance is small, and the Even when used at a low blending ratio of 5 parts or less, mechanical properties such as flexural strength and isot strength can be significantly improved, and there is virtually no deterioration in the heat resistance of the cured product. .

As described above, the glycidyl compound used in the present invention has excellent properties not found in general epoxy resins or flexibility-imparting agents. Useful for materials, etc.

In particular, the glycidyl compound used in the present invention has excellent heat resistance and toughness, and is effective in reducing internal stress in cured products, so it is expected to be applied in fields where mechanical and thermal stress is repeatedly applied.

EXAMPLES Hereinafter, the present invention will be explained in more detail with reference to Examples, but the present invention is not limited in any way by these Examples.

Production Example 1 (Production of sulfonamide compound (1)) 200
Add amine-modified silicone oligomer at both ends (manufactured by Chisso ■) to a four-ml flask with SILAPLANE PM.
-3311, amine equivalent is 493 g/equivalent, general formula (I
) in which R2 is a propylene group, R3 is a methyl group, and n is 11
~12) 49.30g (10 as amino group)
0 mmol), 20 ml of chloroform and 20 ml (100 mmol) of a 1.5N aqueous sodium hydroxide solution were added thereto, and 17.88 g (100 mmol) of benzenesulfonyl chloride was added dropwise over 10 minutes while externally cooling with ice water. Thereafter, the temperature of the contents was raised to 80"C and stirring was continued for 2 hours. The aqueous layer was removed by decantation, and the chloroform was distilled off to obtain 63.15 g of a sulfonamide compound having a siloxane skeleton (hereinafter referred to as sulfonamide). The sulfonamide compound (1) was in a liquid state with low viscosity at room temperature.

The mass balance showed that the reaction progressed almost quantitatively.
Infrared absorption spectrum 3200-33000+11
sulfamoyl group near ', 690, 750 cm-
Absorption of phenyl groups around 1 was confirmed.

Production Example 2 (Production of Glycidyl Compound (1)) 46.3 g of epichlorohydrin and 1.14 g of benzyltriethylammonium chloride (reaction catalyst) were added to 63.15 g of the sulfonamide compound (1) obtained in Production Example 1. The reaction was carried out at ~110°C for 4 hours. 50 contents
The temperature was lowered to .degree. C., and 120.0 ml of a 5N aqueous sodium hydroxide solution was added dropwise over 10 minutes while stirring vigorously. After the dropwise addition was completed, stirring was continued for an additional 2 hours. The aqueous layer containing salts was separated and the organic layer was washed four times with 100 ml of pure water. Excess epichlorohydrin was distilled off under reduced pressure to give 88.23
g glycidyl compound (hereinafter referred to as glycidyl compound (1)
In general formula (1), R1 is a phenyl group, R2 is a propylene group, R3 is a methyl group, and n is 11-12)
I got it. The viscosity of glycidyl compound (1) at 25°C is 2.
It was 8 pages. The epoxy equivalent weight measured by the hydrochloric acid-pyridine method was 729.

Epoxidation rate calculated from epoxy equivalent is 94.5%
The yield was 99.0% based on the theoretical yield.

Example 1 1.0 parts of glycidyl compound (1) and 41.03 parts of 4.4°-diaminodiphenylmethane (hereinafter referred to as DDM
) was heat-melted at 120°C and stirred for 10 minutes.

To this, 10
0 parts were added and mixed with heat to prepare a festival, which was cast into two glass plates sandwiching a 3ma+ spacer. 80℃/2 hours, 120℃/2 hours, 180℃/1
The mixture was then thermally cured at 200° C. for 74 hours to obtain a cured product.

The obtained cured product was cut into a required size using a diamond cutter to prepare a sample, and the sample was subjected to measurement of heat deformation temperature (hereinafter referred to as HDT), bending test, and unnotched Izot impact strength test. The results are shown in Table 1.

In addition, sample pretreatment conditions and physical property measurements are in accordance with JIS K.
The method specified in 8911 was followed.

Examples 2-3 Glycidyl compound (1) to 100 parts of TGDDH
Blend 2.0 parts and 5.0 parts, respectively, and calculate the calculated amount of DD
A cured product was prepared in the same manner as in Example 1, except that the festival was prepared after adding M, and the physical properties were measured. The results are shown in Table 1.

Comparative Example 1 A cured product was prepared in the same manner as in Example 1, except that 100 parts of TGDDM and 40.97 parts of DDM were heated and mixed to prepare a face, and the physical properties were measured. The results are shown in Table 1.

[Margin below]

Example 4 2.0 parts of glycidyl compound (1), 2848 parts of DD
M and 100 parts of Epicoat 828 (oiled shell epoxy ■ Ebisu type epoxy resin, epoxy equivalent weight 18
A cured product was prepared in the same manner as in Example 1, except that the compositions (No. 9) were heated and mixed to prepare a face, and the physical properties were measured. The results are shown in Table 2.

Examples 5-7 Glycidyl compound (
A cured product was prepared in the same manner as in Example 4, except that 5.0 parts, 1000 parts, and 20.0 parts of 1) were blended, and the calculated amount of DDM was added to prepare a face, and the physical properties were measured. . The results are shown in Table 2.

Comparative Example 2 A cured product was prepared in the same manner as in Example 1, except that 100 parts of Epikote 828 and 28.23 parts of DDM were heated and mixed to prepare a face, and the physical properties were measured. The results are shown in Table 2.

〔Effect of the invention〕

Since the composition of the present invention contains a glycidyl compound cut, the bending strength, bending elongation, and isot strength of the cured product are greatly improved. Other than this, the decrease in mechanical properties and heat resistance is very small and is in a range that does not pose any practical problem. By using the composition of the present invention, it is possible to obtain a cured product that has both toughness and heat resistance, which are difficult to achieve with ordinary epoxy resin cured products.

Patent applicant Kanebuchi Chemical Industry Co., Ltd.

Claims (1)

[Claims] 1 (A) General formula (I): ▲There are mathematical formulas, chemical formulas, tables, etc.▼(I) (In the formula, R^1 is a monovalent hydrocarbon group having 1 to 20 carbon atoms,
R^2 is a divalent hydrocarbon group having 1 to 6 carbon atoms, R^3 is a monovalent hydrocarbon group having 1 to 6 carbon atoms, n is an integer of 0 to 50,
X represents a hydrogen atom or a glycidyl group) An epoxy resin composition comprising a glycidyl compound B) an epoxy resin and (C) an epoxy resin curing agent. 2 Glycidyl compound represented by general formula (I) / epoxy resin in a weight ratio of 0.01/99.99 to 50/50
The composition according to claim 1. 3. The composition according to claim 1 or 2, wherein the epoxy resin is an epi-bis type epoxy resin. 4 Epoxy resin has 1 N,N-diglycidylamino group
The composition according to claim 1 or 2, which is an epoxy resin having at least one epoxy resin in the molecule. 5. The composition according to claim 4, wherein the epoxy resin having at least one N,N-diglycidylamino group in one molecule is tetraglycidyldiaminodiphenylmethane and/or a condensation product thereof. 6. The composition according to claim 1, wherein the epoxy resin curing agent is a polyamine having at least two primary amino groups in the molecule. 7 The polyamines are 4,4'- or 3,4'-
The epoxy resin composition according to claim 6, which is diaminodiphenylsulfone or 4,4'- or 3,4'-diaminodiphenylmethane. 8. The composition according to claim 1, wherein the epoxy resin curing agent is an acid anhydride curing agent. 9. The composition according to claim 1, wherein the epoxy resin curing agent is an aliphatic amine curing agent. 10 A claim in which the glycidyl compound represented by the general formula (I) is represented by the general formula: ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (wherein R^2, R^3, n, and X are the same as above) 1. The composition according to item 1. 11 A claim in which the glycidyl compound represented by the general formula (I) is represented by the general formula: ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (wherein R^2, R^3, n, and X are the same as above) 1. The composition according to item 1. 12 A claim in which the glycidyl compound represented by the general formula (I) is represented by the general formula: ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (wherein R^1, R^3, n, and X are the same as above) 1. The composition according to item 1. 13. A cured product obtained by curing the epoxy resin composition according to claim 1.