JP5052209B2 - Novel epoxy compound and method for producing the same - Google Patents

Description

  The present invention relates to a novel epoxy compound useful for raw material applications such as sealing materials, molding materials, casting materials, laminated materials, composite materials, adhesives, and powder coating materials for electrical / electronic / optical components and a method for producing the same. .

  Epoxy compounds are cured with various curing agents to give cured products with excellent mechanical properties, moisture resistance, electrical properties, etc., so sealing materials, molding materials, and casting materials for electrical / electronic / optical components It is used in a wide range of fields such as laminated materials, composite materials, adhesives, and powder coatings. Epoxy compounds have been required to have high performance with respect to heat resistance and the like as technology advances.

  To date, N- (2,3-epoxypropyl) perhydro-4,5-epoxyphthalimide having an imide structure has been proposed for the purpose of improving heat resistance (R. Antoni et al., Makromol. Chem., 194, 411 (1993)), but this method uses epichlorohydrin in the intermediate manufacturing process, so it cannot be avoided that the halogenated residue is mixed into the final product. It is not preferable as a manufacturing method of products for electronic materials that are desired to be reduced to a minimum.

On the other hand, as an organopolysiloxane having an epoxy group-containing organic group, an organopolysiloxane having a 3-glycidoxypropyl group or 2- (3,4-epoxycyclohexyl) ethyl group at the molecular chain terminal or molecular chain side chain or cyclic Siloxane has been proposed (see JP-A-3-255130).
R. Antoni et al., Makromol. Chem., 194, 411 (1993) JP-A-3-255130

However, there is still a need to provide new epoxy compounds that are useful for raw material applications such as sealing materials, molding materials, casting materials, laminated materials, composite materials, adhesives, and powder coatings for electrical, electronic, and optical components. Exists.
As a result of intensive studies to satisfy the above-mentioned needs, the present inventors have obtained the following general formula:

(In the above formula, R ¹ and R ² represent a hydrogen atom, an alkyl group having 1 to 6 carbon atoms or a trialkylsilyl group having 1 to 4 carbon atoms, and R ³ may be the same or different. Each independently represents a hydrogen atom, an alkyl group, an aryl group, an aralkyl group, an alkenyl group or a fluoroalkyl group, and n represents 0 or a positive integer), and the following general formula

(Wherein R ³ represents the same as defined above, R ⁴ represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms or a trialkylsilyl group having 1 to 4 carbon atoms, and n is A new epoxy compound represented by 0 or a positive integer) has been found.
Specifically, the present invention is as described in the following [1] to [11].
[1] The following general formula (I)

(In the above formula, Y is the following formula:

Wherein R ¹ , R ² , R ³ , R ⁴ and n represent the same as defined above).

[2] R ¹ and R ² are hydrogen atoms, or R ¹ is a methyl group, an ethyl group, a propyl group, an isopropyl group, a tertiary butyl group, a trimethylsilyl group, a triethylsilyl group, or a tertiary butyldimethylsilyl group. And R ² is a hydrogen atom, or R ¹ is a hydrogen atom, and R ² is a methyl group, an ethyl group, a propyl group, an isopropyl group, a tertiary butyl group, a trimethylsilyl group, The epoxy compound according to [1], which is either a triethylsilyl group or a tertiary butyldimethylsilyl group.

[3] R ⁴ is a hydrogen atom, or R ⁴ is any one of a methyl group, an ethyl group, a propyl group, an isopropyl group, a tertiary butyl group, a trimethylsilyl group, a triethylsilyl group, and a tertiary butyldimethylsilyl group. The epoxy compound according to the above [1].

[4] The following general formula (II)

( ¹ ), wherein an olefin compound represented by the formula (wherein R ¹ , R ² , R ³ and n represent the same as defined above) is reacted with a peroxide. The manufacturing method of the epoxy compound as described in [2].

[5] In general formula (II), R ¹ and R ² are hydrogen atoms, or R ¹ is a methyl group, an ethyl group, a propyl group, an isopropyl group, a tertiary butyl group, a trimethylsilyl group, a triethylsilyl group, A tertiary butyldimethylsilyl group, and R ² is a hydrogen atom, or R ¹ is a hydrogen atom, and R ² is a methyl group, an ethyl group, a propyl group, an isopropyl group, a tertiary group The production method according to the above [4], which is any one of a butyl group, a trimethylsilyl group, a triethylsilyl group, and a tertiary butyldimethylsilyl group.

[6] The following general formula (III)

(Wherein R ¹ and R ² represent the same as defined above), an epoxy compound represented by the following general formula (IV)

(Wherein R ³ and n represent the same as defined above), and reacting with a silicon compound represented by the above [1] or [2] .

[7] In general formula (III), R ¹ and R ² are hydrogen atoms, or R ¹ is a methyl group, an ethyl group, a propyl group, an isopropyl group, a tertiary butyl group, a trimethylsilyl group, a triethylsilyl group, A tertiary butyldimethylsilyl group, and R ² is a hydrogen atom, or R ¹ is a hydrogen atom, and R ² is a methyl group, an ethyl group, a propyl group, an isopropyl group, a tertiary group The production method according to [6] above, which is any one of a butyl group, a trimethylsilyl group, a triethylsilyl group, and a tertiary butyldimethylsilyl group.

[8] The following general formula (V)

(1) or (3), wherein an olefin compound represented by the formula (wherein R ³ , R ⁴ and n represent the same as defined above) is reacted with a peroxide. The manufacturing method of the epoxy compound of description.

[9] In general formula (V), R ⁴ is a hydrogen atom, or R ⁴ is a methyl group, ethyl group, propyl group, isopropyl group, tertiary butyl group, trimethylsilyl group, triethylsilyl group, tertiary butyl. The production method according to [8] above, which is any one of dimethylsilyl groups.

[10] The following general formula (VI)

(Wherein R ⁴ represents the same as defined above), an epoxy compound represented by the following general formula (IV)

(Wherein R ³ and n represent the same as defined above), and reacting with the silicon compound represented by the above [1] or [3] .

[11] In general formula (VI), R ⁴ is a hydrogen atom, or R ⁴ is a methyl group, ethyl group, propyl group, isopropyl group, tertiary butyl group, trimethylsilyl group, triethylsilyl group, tertiary butyl. The production method of the above-mentioned [10], which is any one of dimethylsilyl groups.

  The novel epoxy compound of the present invention is useful in a wide range of fields such as sealing materials for electric / electronic / optical components, molding materials, casting materials, laminated materials, composite materials, adhesives, and powder coatings.

  Hereinafter, preferred embodiments of the present invention will be described, but it should be understood that the present invention is not limited to only these embodiments, and various modifications can be made within the spirit and scope of the present invention.

In the present invention, the aforementioned R ¹ specifically includes a hydrogen atom, a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a tertiary butyl group, a pentyl group, a hexyl group, and a trimethylsilyl group. , Triethylsilyl group, tertiary butyldimethylsilyl group and the like are exemplified, but not limited thereto. R ¹ is more preferably a hydrogen atom, a methyl group, a trimethylsilyl group, or a tertiary butyldimethylsilyl group.

Specific examples of R ² include a hydrogen atom, methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, tertiary butyl group, pentyl group, hexyl group, trimethylsilyl group, triethylsilyl group, and tertiary group. Examples include but are not limited to a butylbutylsilyl group. R ² is more preferably a hydrogen atom, a methyl group, a trimethylsilyl group, or a tertiary butyldimethylsilyl group.
Specific examples of R ³ include a hydrogen atom, an alkyl group such as a methyl group, an ethyl group, a propyl group, and a butyl group, an aryl group such as a phenyl group, a tolyl group, and a xylyl group, and an aralkyl group such as a benzyl group and a phenethyl group. Groups, vinyl groups, allyl groups, butenyl groups, pentenyl groups, hexenyl groups and other alkenyl groups, 3,3,3-trifluoropropyl groups and other fluoroalkyl groups, etc., but are not limited thereto. Absent. R ³ is more preferably a hydrogen atom, a methyl group, or a 3,3,3-trifluoropropyl group.

n is preferably an integer of 1 to 500.
Specific examples of R ⁴ include a hydrogen atom, methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, tertiary butyl group, pentyl group, hexyl group, trimethylsilyl group, triethylsilyl group, and tertiary group. Examples include but are not limited to a butylbutylsilyl group. R ⁴ is more preferably a hydrogen atom, a methyl group, a trimethylsilyl group, or a tertiary butyldimethylsilyl group.

  The novel epoxy compound represented by general formula (I) of the present invention can be produced by reacting an olefin compound represented by general formula (II) or general formula (V) with a peroxide.

As the peroxide, any industrially usable one can be used without exception, such as hydrogen peroxide, formic acid, peracetic acid, 3-chloroperoxybenzoic acid, cumene peroxide, dimethyldioxirane. Alkyl peroxides such as can be used. Preferred peroxides are hydrogen peroxide, peracetic acid and 3-chloroperoxybenzoic acid, more preferably hydrogen peroxide and peracetic acid.
When hydrogen peroxide is used as the peroxide, the concentration of the hydrogen peroxide solution to be used is not limited, and the reaction to the olefin compound occurs depending on the concentration, but generally 1 to 80%, preferably 20 to 60%. It is chosen from the range.

The amount of the aqueous hydrogen peroxide used is not particularly limited, and the reaction to the olefin compound occurs depending on the amount used, but generally 0.8 to 10.0 equivalents, preferably 1.0, with respect to the olefin compound. It is chosen from the range of -3.0 equivalent.
In the oxidation reaction with hydrogen peroxide, the reaction can be performed in the presence of quaternary ammonium hydrogen sulfate and a catalytic amount of a Group 6 metal compound such as molybdenum or tungsten.

  Examples of the quaternary ammonium hydrogen sulfate include tetrahexylammonium hydrogen sulfate, tetraoctylammonium hydrogensulfate, methyltrioctylammonium hydrogensulfate, tetrabutylammonium hydrogensulfate, ethyltrioctylammonium hydrogensulfate, cetylpyridinium hydrogensulfate and the like. Among them, tetrahexylammonium hydrogen sulfate, tetraoctylammonium hydrogensulfate, methyltrioctylammonium hydrogensulfate, and the like are preferable. These quaternary ammonium hydrogen sulfates may be used alone or in combination of two or more. The amount to be used is preferably selected from the range of 0.0001 to 10 mol%, more preferably 0.01 to 5 mol%, based on the olefin compound of the substrate.

  In the case of molybdenum, the Group 6 metal compound includes a compound that generates a molybdate anion in water. For example, molybdic acid, molybdenum trioxide, molybdenum trisulfide, molybdenum hexachloride, phosphomolybdic acid, ammonium molybdate, molybdenum Potassium acid dihydrate, sodium molybdate dihydrate, and the like, among which molybdic acid, molybdenum trioxide, and phosphomolybdic acid are preferable. In the case of tungsten, examples include compounds that generate tungstate anions in water, such as tungstic acid, tungsten trioxide, tungsten trisulfide, tungsten hexachloride, phosphotungstic acid, ammonium tungstate, potassium tungstate dihydrate, There are sodium tungstate dihydrate and the like. Among these, tungstic acid, tungsten trioxide, phosphotungstic acid, sodium tungstate dihydrate and the like are preferable. These group 6 metal compounds may be used alone or in combination of two or more. The amount to be used is preferably selected from the range of 0.0001 to 20 mol%, more preferably 0.01 to 10 mol%, based on the olefin compound of the substrate.

Note that this type of catalyst may be modified by using additives such as phosphoric acid, polyphosphoric acid, aminomethylphosphonic acid, sodium phosphate.
In the production method by the oxidation reaction with hydrogen peroxide, the reaction is usually performed in the range of 30 to 100 ° C, preferably in the range of 50 to 90 ° C.

When peracetic acid is used as the peroxide, the concentration of the acetic acid solution of peracetic acid to be used is not limited, and is generally selected from the range of 1 to 80%, preferably 9 to 40%. Moreover, there is no restriction | limiting in the usage-amount of the acetic acid solution of peracetic acid, Generally it is chosen from the range of 0.8-10.0 equivalent with respect to an olefin compound, Preferably it is 1.0-2.0 equivalent.
The oxidation reaction of peracetic acid with an acetic acid solution may be performed without a solvent, but can also be performed using a solvent. Any solvent can be selected as long as it is soluble. Specifically, hexane, heptane, octane, decane, ethyl acetate, toluene, xylene, chloroform, dichloromethane, dichloroethane, tetrachloroethane, and any mixture thereof are required. The reaction can be carried out in the air or in an inert gas atmosphere such as nitrogen or argon.

  The olefin compound represented by the general formula (II) and the general formula (V) which is a precursor of the novel epoxy compound of the present invention can be obtained by an imidation reaction from a corresponding acid anhydride and diamine. In this reaction, in addition to xylene, toluene, metaxylene, orthoxylene, paraxylene, mesitylene, and any mixture thereof can be used as necessary, and the reaction can be performed in the air or with nitrogen, argon, It can carry out in inert gas atmosphere. Furthermore, this reaction can also be carried out by adding an additive such as a polymerization inhibitor.

Moreover, the novel epoxy compound represented by the general formula (I) of the present invention reacts the epoxy compound represented by the general formula (III) or the general formula (VI) with the silicon compound represented by the general formula (IV). Can be manufactured.
This hydrosilylation reaction can be carried out in the presence of a catalyst. As a catalyst used for this, there is a known addition reaction catalyst, for example, a platinum-based catalyst such as chloroplatinic acid, which is heated in the presence of such a catalyst. Can be done. When the epoxy compound represented by the general formula (III) or the general formula (VI) is reacted with the silicon compound represented by the general formula (IV), the ratio of both compounds is usually the allyl group 1 of the epoxy compound. The number of —SiH groups of the silicon compound is preferably in the range of 0.001 to 1.5, and preferably in the range of 0.005 to 1.

  In this hydrosilylation reaction, it is preferable to heat to 60 to 140 ° C. in an inert solvent such as benzene, toluene and methyl isobutyl ketone. The amount of these solvents used is usually 30 to 400% by mass based on the total weight of the epoxy compound of general formula (III) or general formula (VI) and the silicon compound represented by general formula (IV). It is good, Preferably it is 50-300 mass%. The reaction time is usually 1 to 24 hours, preferably 2 to 10 hours. After the reaction is completed, the novel epoxy compound of the present invention can be obtained by washing with water and distilling off the solvent under heating and reduced pressure.

  Any of the general methods can be used to purify the product obtained by the above-described method. For example, adsorption separation, specifically adsorption removal of impurities and colored substances using an adsorbent such as activated carbon, acid clay, activated clay, or column chromatography, thin layer chromatography, specifically silica gel, hydrous silica gel, alumina Column chromatography using activated carbon, titania, zirconia, more specifically silica gel, hydrous silica gel, and alumina as fillers. Further, it can be purified by distillation, specifically, vacuum distillation or molecular distillation.

EXAMPLES Hereinafter, although this invention is further demonstrated using an Example, this invention is not limited only to these Examples.
Reference example 1
In a 300 ml three-necked flask equipped with a reflux condenser, a thermometer, a Dean-Stark moisture separator, a stirrer, a dropping funnel and an oil bath, 16.75 g of cis-4-cyclohexene-1,2-dicarboxylic acid anhydride and 146. 0 g was charged. After heating to 70 ° C. with stirring under a nitrogen atmosphere to obtain a uniform solution, the following formula (VII)

41.05 g of the silicon compound represented by the formula is dropped over 20 minutes with a dropping funnel, and after aging for 30 minutes, the oil bath is heated to 160 ° C. and collected using a Dean-Stark moisture separator. While removing water, the mixture was heated to reflux for 24 hours and then cooled to room temperature.
The solvent was removed from the contents in the flask using a rotary evaporator and purified by column chromatography to obtain the following formula (VIII)

Was obtained as a slightly yellow transparent liquid.
Reference example 2
A 1 L four-necked flask equipped with a reflux condenser, a thermometer, a stirring device, a dropping funnel and an oil bath was charged with 304.3 g of cis-4-cyclohexene-1,2-dicarboxylic acid anhydride and 280 g of toluene. To this, 116.5 g of allylamine was added dropwise over 90 minutes using a dropping funnel in a nitrogen atmosphere, and after aging for 30 minutes, a Dean-Stark moisture separator was attached to a separable flask and an oil bath maintained at 140 ° C. was used. Then, while removing the collected water, the mixture was heated to reflux for 5 hours and then cooled to room temperature.
The solvent was removed from the contents in the flask using a rotary evaporator to obtain 344.3 g of a crude N-allyl-4-cyclohexene-1,2-dicarboxy product. Purification by vacuum distillation gave 273.5 g of N-allyl-4-cyclohexene-1,2-dicarboximide as a colorless and transparent liquid.

  In a 50 ml three-necked flask equipped with a reflux condenser, thermometer, stirring device, dropping funnel and oil bath, 100.0 g of N-allyl-4-cyclohexene-1,2-dicarboximide, methyl trioctylammonium hydrogen sulfate 2.44 g, 3.45 g of sodium tungstate dihydrate, and 0.58 g of aminomethylphosphonic acid were charged. The mixture was heated using an oil bath maintained at 90 ° C., 80 ml of 30% aqueous hydrogen peroxide was dropped over 180 minutes through a dropping funnel, and aged for 4 hours. After cooling in an ice bath and removing excess hydrogen peroxide with 300 ml of a saturated aqueous sodium thiosulfate solution, the mixture was extracted twice with 200 ml of ethyl acetate. The obtained ethyl acetate solution was dried over anhydrous sodium sulfate overnight, the solvent ethyl acetate was removed using a rotary evaporator, and then purified by column chromatography packed with 25% hydrous silica gel to obtain 4,5- 78.9 g of epoxy-N-allylcyclohexane-1,2-dicarboximide was obtained.

Example 1
A 200 ml three-necked flask equipped with a reflux condenser, a thermometer, a stirrer, a dropping funnel and an oil bath was charged with 17.5 g of the olefin compound represented by the formula (VIII) obtained in Reference Example 1 and 10 ml of ethyl acetate. .
It heated using the oil bath kept at 60 degreeC, 12.0g of 40% peracetic acid was dripped over 1 hour with the dropping funnel, and it was aged for 1 hour as it was. Next, the temperature of the oil bath was set to 70 ° C., and the mixture was further aged for 1 hour. The mixture was cooled in an ice bath, excess peracetic acid was removed with 15 ml of a saturated aqueous sodium thiosulfate solution, and then extracted three times with 25 ml of ethyl acetate. The obtained ethyl acetate solution was dried over anhydrous sodium sulfate overnight, the solvent ethyl acetate was removed using a rotary evaporator and purified by column chromatography, and the following formula (IX)

18.3 g of an epoxy compound represented by the formula:
The above structure was confirmed by measuring ¹ H-NMR, ¹³ C-NMR and ²⁹ Si-NMR of this epoxy compound in a deuterated chloroform solvent using a nuclear magnetic resonance apparatus AL-400 manufactured by JEOL Ltd. We were able to. The ¹ H-NMR, ¹³ C-NMR and ²⁹ Si-NMR spectra of the epoxy compound represented by the formula (IX) are shown in FIG. 1, FIG. 2 and FIG. 3, respectively.

Example 2
4,5-epoxy-N-allylcyclohexane-1 obtained in Reference Example 2 was added to a 300 ml four-necked flask equipped with a reflux condenser, a Dean-Stark type water separator, a thermometer, a stirrer, a dropping funnel and an oil bath. , 2-dicarboximide 22.8 g, toluene 180 g, 2% by mass of 2-chlorohexanoic acid 2-ethylhexanol solution 0.05 g, and azeotropic dehydration while refluxing for 1 hour using an oil bath maintained at 140 ° C After confirming that water is not distilled off, the following formula (X)

The total amount of 36.3 g of the silicon compound represented by the formula was added dropwise using a dropping funnel over 30 minutes. Further, the mixture was refluxed for 4 hours and then cooled to room temperature. After removing the catalyst by washing three times with water, the solvent was removed using a rotary evaporator and purified by column chromatography to obtain 40.2 g of an epoxy compound represented by the formula (IX).
When ¹ H-NMR, ¹³ C-NMR and ²⁹ Si-NMR of this epoxy compound were measured in a deuterated chloroform solvent using a JEOL nuclear magnetic resonance apparatus AL-400, the same as in Example 1 was obtained. Thus, the structure of the formula (IX) of this epoxy compound could be confirmed.

  The novel epoxy compound of the present invention is useful in a wide range of fields such as sealing materials for electric / electronic / optical components, molding materials, casting materials, laminated materials, composite materials, adhesives, and powder coatings.

1 is a chart showing a ¹ H-NMR spectrum of an epoxy compound represented by formula (IX) obtained in Example 1. The chart which shows the ¹³ C-NMR spectrum of the epoxy compound represented by Formula (IX) obtained in Example 1. FIG. The chart which shows ²⁹ Si-NMR of the epoxy compound represented by Formula (IX) obtained in Example 1. FIG.

Claims (11)

The following general formula (I)

(In the above formula, Y is the following formula:

Wherein R ¹ and R ² represent a hydrogen atom, an alkyl group having 1 to 6 carbon atoms or a trialkylsilyl group having 1 to 4 carbon atoms, and R ³ is the same or different from each other. Each independently represents a hydrogen atom, an alkyl group, an aryl group, an aralkyl group, an alkenyl group or a fluoroalkyl group, and R ⁴ represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms or a carbon atom having 1 to 6 carbon atoms. An epoxy compound represented by a trialkylsilyl group of up to 4 and n represents 0 or a positive integer. R ¹ and R ² are hydrogen atoms, or R ¹ is any ^one of a methyl group, an ethyl group, a propyl group, an isopropyl group, a tertiary butyl group, a trimethylsilyl group, a triethylsilyl group, and a tertiary butyldimethylsilyl group. And R ² is a hydrogen atom, or R ¹ is a hydrogen atom, and R ² is a methyl group, an ethyl group, a propyl group, an isopropyl group, a tertiary butyl group, a trimethylsilyl group, or a triethylsilyl group. The epoxy compound according to claim 1, which is any one of tertiary butyldimethylsilyl groups. R ⁴ is a hydrogen atom, or R ⁴ is any one of a methyl group, an ethyl group, a propyl group, an isopropyl group, a tertiary butyl group, a trimethylsilyl group, a triethylsilyl group, and a tertiary butyldimethylsilyl group, Item 4. The epoxy compound according to Item 1. The following general formula (II)

An olefin compound represented by the formula (wherein R ¹ , R ² , R ³ and n represent the same as defined above) is reacted with a peroxide. The manufacturing method of the epoxy compound of description. In the general formula (II), R ¹ and R ² are hydrogen atoms, or R ¹ is a methyl group, ethyl group, propyl group, isopropyl group, tertiary butyl group, trimethylsilyl group, triethylsilyl group, tertiary butyl Either a dimethylsilyl group, and R ² is a hydrogen atom, or R ¹ is a hydrogen atom, and R ² is a methyl group, an ethyl group, a propyl group, an isopropyl group, or a tertiary butyl group. The production method according to claim 4, which is any one of a trimethylsilyl group, a triethylsilyl group, and a tertiary butyldimethylsilyl group. The following general formula (III)

(Wherein R ¹ and R ² represent the same as defined above), an epoxy compound represented by the following general formula (IV)

The method for producing an epoxy compound according to claim 1, wherein the compound is reacted with a silicon compound represented by the formula (wherein R ³ and n represent the same as defined above). In general formula (III), R ¹ and R ² are hydrogen atoms, or R ¹ is a methyl group, ethyl group, propyl group, isopropyl group, tertiary butyl group, trimethylsilyl group, triethylsilyl group, tertiary butyl. Either a dimethylsilyl group, and R ² is a hydrogen atom, or R ¹ is a hydrogen atom, and R ² is a methyl group, an ethyl group, a propyl group, an isopropyl group, or a tertiary butyl group. , A trimethylsilyl group, a triethylsilyl group, or a tertiary butyldimethylsilyl group. The following general formula (V)

The olefin compound represented by (in the above formula, R ³ , R ⁴ and n represent the same as defined above) is reacted with a peroxide. A method for producing an epoxy compound. In general formula (V), R ⁴ is a hydrogen atom, or R ⁴ is a methyl group, an ethyl group, a propyl group, an isopropyl group, a tertiary butyl group, a trimethylsilyl group, a triethylsilyl group, or a tertiary butyldimethylsilyl group. The manufacturing method according to claim 8, which is any one of the following. The following general formula (VI)

(Wherein R ⁴ represents the same as defined above), an epoxy compound represented by the following general formula (IV)

The method for producing an epoxy compound according to claim 1, wherein the compound is reacted with a silicon compound represented by the formula (wherein R ³ and n represent the same as defined above). In general formula (VI), R ⁴ is a hydrogen atom, or R ⁴ is a methyl group, an ethyl group, a propyl group, an isopropyl group, a tertiary butyl group, a trimethylsilyl group, a triethylsilyl group, or a tertiary butyldimethylsilyl group. The manufacturing method according to claim 10, which is any one of the above.

Images