KR20130134113A - Novel non-halogen epoxy compound containing nitrogen compound and their compositions - Google Patents

Abstract

The present invention relates to novel non-halogen-based flame-retardant epoxy compounds and compositions containing nitrogen-based organic compounds and, more particularly, to novel non-halogen-based flame-retardant epoxy compounds that contain nitrogen-based organic compounds and are useful a raw material for preparing the flame-retardant agent, and compositions comprising the same. The compounds and compositions are useful for an insulating material for electric and electronic products, various kinds of composite materials such as laminated plates or CFRP, adhesives, and paints

Description

Novel Non-Halogen Epoxy Compound Containing Nitrogen Compound and Their Compositions

The present invention relates to novel non-halogen flame-retardant epoxy resin compounds and compositions containing nitrogen-based organic compounds, and more particularly, to new non-halogen-containing non-halogen-containing organic compounds useful as flame retardants of organic polymer materials or raw materials for their preparation. A flame retardant epoxy resin compound and composition are disclosed.

BACKGROUND ART Conventionally, as a flame retardant for a flammable polymer material, a halogen-based flame retardant excellent in a flame retarding effect and an economical view has been widely used. Among them, a bromine-based compound having excellent flame retardancy is used in most general-purpose resins, and a flame retardant is used together with a bromine-based flame retardant or an antimony-based flame retardant such as antimony trioxide as an adjuvant in order to improve flame retardancy. However, brominated flame retardants may generate toxic gases such as HBr in the event of a fire, which may cause aquaculture and may generate dioxine, which is a strong carcinogen when burned. Furthermore, antimony flame retardants used in combination with brominated flame retardants also have their own carcinogenic properties, leading to restrictions on their use in Europe.

Accordingly, in recent years, research on non-halogen flame retardant compounds has been actively conducted, and various eco-friendly flame retardant compounds have been developed.

Such non-halogen flame retardant compounds include phosphorus-based, nitrogen-based compounds, silicon-based, boron-based flame retardants, or metal oxides or metal hydroxides. Among these, organophosphorus compounds and organic nitrogen compounds are most actively considered as flame retardant compounds that can replace halogen flame retardants.

In particular, triphenylphosphate (TPP) is known as the most basic compound among organophosphorus compounds. However, since TPP has a small molecular weight, there is a problem that it is easily volatilized during the molding process of a polymer material carried out at a high temperature, and also has a problem of deteriorating the softening point of the resin and the mechanical properties by acting as a plasticizer of the polymer material. Further, since the flame retardant is easily eluted from the resin, there is a problem that the flame retardancy is lowered and secondary contamination is generated.

In order to solve this problem, Japanese Patent Laid-Open Publication No. 59-202240 and Japanese Patent Laid-Open Publication No. Hei 2-18336 use hydroquinone, resorcinol, bisphenol derivatives, and the like to form condensed phosphorus flame retardant compounds containing two phosphorus elements in a molecule. It is starting to use. However, the condensed phosphorus-based flame retardant compound also has a problem that the storage stability is deteriorated with time, and the effect is significantly lower than that of the conventional halogen-based flame retardant compound in terms of heat resistance, hydrolysis resistance, and flame retardancy. In addition, when the phosphate ester type TPP or condensed phosphorus flame retardant compound is added to an ester type polymer resin (PET, PC, etc.), there is a problem of deterioration of resin properties due to a transesterification reaction.

Accordingly, the present inventors have endeavored to develop a practical non-halogen-based flame-retardant epoxy resin, and as a starting material, aminophenol containing nitrogen, which is a non-halogen-based element, is used as a starting material. It was confirmed that the present invention can be stably produced, and the present invention was completed.

It is a main object of the present invention to provide a non-halogen-based novel epoxy compound having excellent storage stability at high temperatures and implementing flame retardancy and a method of preparing the new epoxy compound.

The present invention also provides a non-halogen flame-retardant epoxy resin useful for various composite materials, such as insulating materials for electrical and electronic products, laminates and carbon fiber reinforced plastics (CFRP), adhesives and paints.

In order to achieve the above object, the present invention provides an epoxy compound represented by the following formula (1).

[Formula 1]

In Formula 1, n is an integer of 1 to 10.

The present invention also comprises the steps of (a) reacting an aminophenol and a compound represented by the formula (2) to produce a compound represented by the formula (3); And (b) preparing an epoxy compound represented by Chemical Formula 1 by epoxidizing the compound represented by Chemical Formula 3 with an epihalohydrin compound to produce an epoxy compound represented by Chemical Formula 1. to provide.

[Formula 1]

In the general formula (1), n is an integer of 1 to 10.

(2)

(3)

The present invention also provides an epoxy resin composition comprising an epoxy compound represented by the formula (1) and a curing agent.

[Formula 1]

In the general formula (1), n is an integer of 1 to 10.

The epoxy compound according to the present invention does not contain a halogen element, which is environmentally friendly, has excellent high temperature stability, and exhibits excellent flame retardancy even without the addition of a flame retardant and a flame retardant aid. In addition to providing a suitable use for molding applications, the flame retardancy can increase the human body stability and further contribute to environmental protection when the epoxy resin is used in various home appliances, industrial products, etc. have.

1 is a graph of gel permeation chromatography of an epoxy compound according to an embodiment of the present invention.
2 is a FT-IR measurement graph of the epoxy compound according to an embodiment of the present invention.
3 is a graph of gel permeation chromatography of an epoxy compound according to another embodiment of the present invention.
4 is a FT-IR measurement graph of the epoxy compound according to another embodiment of the present invention.

Unless otherwise defined, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs. In general, the nomenclature used herein is well known and commonly used in the art.

Throughout this specification, when an element is referred to as "including " an element, it is understood that the element may include other elements as well, without departing from the other elements unless specifically stated otherwise.

The present invention relates to an epoxy compound represented by the following Chemical Formula 1 in one aspect, and relates to a novel epoxy compound useful as a flame retardant of an organic polymer material or a raw material for producing the same.

[Formula 1]

In Formula 1, n is an integer of 1 to 10.

Epoxy compound comprising a repeating unit represented by the formula (1) according to the present invention, in the general formula (1), the average value of n indicating the degree of polymerization can be 1 to 10, preferably from 1 to 10 in terms of having a suitable mechanical strength It is five.

In addition, the epoxy compound represented by Formula 1 according to the present invention improves the flame retardant properties of the compound itself by containing nitrogen in the epoxy compound, and further, by modifying the nitrogen-based compound into a tertiary amine form that first regulates the reactivity Next, by performing the epoxidation reaction, stability can be maintained even at the process conditions that proceed at a high temperature during the epoxidation process, and there is an advantage that physical properties do not change even after a long time.

Since the epoxy compound represented by Formula 1 according to the present invention has an epoxy equivalent of 120 g / eq to 360 g / eq, when the above range is satisfied, it is easy to control to various compounding ratios due to the characteristics of the dosage of epoxy and the curing agent determined as the equivalent ratio. In addition, various kinds of curing agents may be used, and various properties of the composite curing may be expressed. In addition, the weight-average molecular weight of 300g / mol ~ 6,000g / mol can prevent the degradation of workability due to the high molecular weight is convenient to use, it is possible to avoid the problem of heat resistance degradation due to low molecular weight.

In another aspect, (a) condensation reaction of an aminophenol (aminophenol) and a compound represented by Formula 2 to produce a compound represented by Formula 3; And (b) epoxidizing the compound represented by Chemical Formula 3 with an epihalohydrin compound to prepare an epoxy compound represented by Chemical Formula 1, in the method of preparing an epoxy compound represented by Chemical Formula 1 It is about.

[Formula 1]

In the general formula (1), n is an integer of 1 to 10.

(2)

(3)

In the reaction of a conventional nitrogen-based raw material and epihalohydrin, a sudden runaway reaction occurs due to the primary or secondary amines remaining in the reaction process. In particular, during such a high temperature process such as recovery of unreacted epihalohydrin and recovery of solvent, such rapid runaway reaction proceeds to gelation and excessively generates secondary reactants, resulting in lower yield and workability. There is a problem in the manufacturing process. Accordingly, the present invention is to solve the above problems, by modifying the nitrogen-based raw material to control the reactivity of the amine, which is an unstable raw material, to establish the content and reaction conditions of the reactant high yield of nitrogen-based flame retardant epoxy resin excellent in high stability It can be prepared as.

More specifically, the epoxy compound represented by Formula 1 of the present invention is condensation reaction of aminophenol (aminophenol) and the compound represented by Formula 2 to produce a compound represented by Formula 3, and then represented by the The compound can be obtained by epoxidation with an epihalohydrin compound. This is summarized in Scheme 1 below.

[Reaction Scheme 1]

In Scheme 1, X is F, Cl, Br or I, n is an integer from 1 to 10.

In the present invention, the compound represented by the formula (3) is obtained by one-to-one reaction with 1 mole of the compound represented by the formula (2) with respect to 1 mole of the aminophenol, and beyond this range, one raw material is not used and is left unreacted. This may be economically disadvantageous.

At this time, the reaction is carried out for 3 to 5 hours at 20 ~ 40 ℃, less than 20 ℃ reaction rate is slow, the reaction may not be completed within a practical process time. In addition, the reaction rate is faster than 40 ℃, there is a problem that the secondary reactant is produced.

In the above reaction, the solvent is an isopropyl alcohol as a co-solvent, as long as it is necessary for dissolving and diluting the raw material, controlling the reaction temperature, securing the volume required for stirring, or facilitating the reaction. It may select arbitrarily from alcohols, such as butyl alcohol, methyl alcohol, and ethyl alcohol, and may use it in arbitrary quantities. In addition, it is not specifically limited to 1 type, You may mix and use.

As described above, the compound represented by Chemical Formula 3 prepared is epoxidized with an epihalohydrin compound to prepare a final compound represented by Chemical Formula 1.

As epihalohydrin used in the epoxidation reaction, it is preferable to use epichlorohydrin from an industrial point of view, and the reaction for obtaining the epoxy compound may be used without any conventionally known method. For example, a solid of an alkali metal hydroxide such as sodium hydroxide or potassium hydroxide is added to a mixture of the compound represented by Formula 3 and epihalohydrin at once, or in a temperature range of 20 to 120 ° C. for 1 to 20 hours. This can be done by dropwise addition.

The amount of epihalohydrin used in the reaction is preferably 1 to 10 moles, more preferably 4 to 8 moles, based on 1 equivalent of the hydroxyl group (OH) of the compound represented by Formula 3. It is good. The amount of the alkali metal hydroxide used in the reaction is preferably 0.5 to 2 moles, more preferably 0.5 to 1.5 moles per 1 equivalent of the hydroxyl group of the compound represented by the formula (3).

In the present invention, after completion of the epoxidation reaction, water washing (or under heating and reduced pressure without washing with water) is used to remove excess epihalohydrin, which is dissolved in a solvent such as methyl isobutyl ketone, toluene, xylene, and hydroxide. It is preferable to add an aqueous solution of an alkali metal hydroxide such as sodium or potassium hydroxide to carry out the reaction once again to remove unreacted hydrolyzable chlorine. In this case, the amount of the alkali metal hydroxide is preferably used 1 to 4 mol, more preferably 2 to 3 mol relative to the hydrolyzable chlorine content in the compound represented by the formula (3). The reaction is preferably performed for 1 to 4 hours at 70 ~ 90 ℃.

After completion | finish of reaction, the salt which generate | occur | produced is washed with water, and solvents, such as methyl isobutyl ketone, toluene, and xylene, are removed under heating and pressure reduction. Through such a process, there is an advantage that an epoxy compound having a low content of unreacted hydrolyzable chlorine may be obtained.

The epoxy resin obtained through the above process may include a compound in which one hydroxyl group does not become an epoxide among two phenolic hydroxyl groups, and may also include an oligomer type generated by a side reaction in which the phenolic hydroxyl group attacks the epoxide. Can be.

In another aspect, the present invention relates to an epoxy resin composition comprising an epoxy compound represented by the formula (1) and a curing agent.

[Formula 1]

In Formula 1, n is an integer of 1 to 10.

The epoxy resin composition of this invention can be used individually or in parallel with another epoxy compound resin. When used in combination with other epoxy resins, it is preferable to use 10 wt% to 99.9 wt% of the epoxy compound represented by Formula 1 of the present invention.

The epoxy resin that can be used in combination with the epoxy compound represented by the formula (1) according to the present invention is not limited, but is preferably a novolak type epoxy resin, a biphenyl type epoxy resin, a bisphenol A type epoxy resin, a bisphenol F type epoxy resin , Bisphenol S type epoxy resin, glycidyl amine epoxy resin, glycidyl ester epoxy resin and the like can be used. These may be used independently and may mix and use 2 or more types.

Although the epoxy resin composition of this invention contains a hardening | curing agent and does not limit the kind of hardening | curing agent which can be used, Preferably it is a phenol novolak resin, a cresol novolak resin, a biphenyl containing phenyl novolak resin, phenol-p-xylene Acid anhydrides such as phenolic curing agents such as phenolic resins and phenyl biphenylene phenolic resins, amine based curing agents such as aliphatic polyamines, polyamide polyamines and aromatic polyamines, dicyandiamides, hexahydrophthalic anhydride and methyltetrahydrophthalic anhydride. System curing agents can be used. These may be used independently or may be used in combination of 2 or more type.

As for the usage-amount of a hardening | curing agent in the epoxy resin composition of this invention, 0.5-1.5 equivalent is preferable with respect to 1 equivalent of epoxy groups of an epoxy compound, More preferably, 0.6-1.2 equivalent is used. When the curing agent is used in less than 0.5 equivalent to 1 equivalent of epoxy group of epoxy resin, there is a problem of not being sufficiently cured, resulting in poor physical properties, even when using more than 1.5 equivalents to 1 equivalent of epoxy group of epoxy resin. There is a problem that the physical properties are lowered.

The epoxy composition of this invention can add and use a well-known additive as needed. The type of the additive is not limited, but preferably, inorganic fillers such as silica, alumina, talc and glass fibers, release agents such as higher fatty acids, higher fatty acid metal salts, ester waxes and natural waxes, epoxysilanes, aminosilanes and alkylsilanes. Coupling agents, auxiliary flame retardants, etc. can be used as needed.

The epoxy resin composition of the present invention obtained as described above can be used in a wide range of fields requiring flame retardancy, heat resistance, moisture resistance, and high adhesion. Specifically, it is useful as a compounding component of all electrical and electronic materials such as insulating materials, laminates, encapsulation materials, and can also be used in fields such as molding materials, composite materials, paints, and adhesives.

Hereinafter, the present invention will be described in detail with reference to Examples, but the present invention is not limited by these Examples.

Example  1: epoxy compound and copper foil according to the present invention Laminate  Produce

1-1: Epoxy Compound Synthesis

Into a flask equipped with a reflux condenser, 1,050 g of epichlorohydrin, 135 g of aminophenol, and 120 g of salicylic aldehyde were added, followed by stirring at 30 ° C. for 4 hours to react the aminophenol and salicylic aldehyde. 12 g was added at 60 ° C., and preliminary reaction was performed at the same temperature for 4 hours. After completion of the prereaction, the pressure was reduced to 150torr, and then 275 g of 50wt% sodium hydroxide was added dropwise at 60 ° C for 4 hours. After completion of the dropwise addition, the temperature was raised to 155 ° C to recover unreacted epichlorohydrin for 2 hours. 320 g of methyl isobutyl ketone was added to the reaction product from which the unreacted epichlorohydrin was recovered to dissolve the reactant, and distilled water was added to remove the salt through water separation, followed by purification by adding 50 wt% sodium hydroxide. Phosphoric acid was added to neutralize the purified reaction product, and the mixture was decompressed at 155 ° C for 3 hours to recover methyl isobutyl ketone, thereby obtaining 315 g of an epoxy compound (yield 92%). Gel permeation chromatography of the epoxy compound thus obtained (Waters 815 pump, 715 Injector, 2414 RI detector) and FT-IR (PerkinElmer Spectrum 10) are shown in Figs.

As shown in FIG. 1, the epoxy compound prepared in Example 1 has a mass average molecular weight of 1,111 g / mol, a molecular weight distribution of 2.7, an epoxy equivalent of 181.3 g / eq, and a hydrolyzable chlorine of 0.06 wt%. Confirmed. In addition, as shown in FIG. 2, as a result of the FT-IR analysis, the characteristic peaks of the Ar-OC bonds formed by the reaction of the nitrogen-based compound and epichlorohydrin and the characteristic peaks of the epoxy ring were confirmed (FT-IR analysis: ^{Ar-OC: 1239 ㎝ -1 &} 1039㎝ -1, Epoxy ring: 911㎝ -1 & 818㎝ -1).

1-2: copper foil Laminate  Produce

The epoxy compound prepared in Example 1 was dissolved in methyl ethyl ketone at a nonvolatile content of 70 wt%, and dicyandiamide as a curing agent was added in an amount of 3 parts by weight based on 100 parts by weight of the epoxy resin solids, and 2-methyl as a curing accelerator. The varnish was prepared by mixing imidazole in an amount of 0.14 parts by weight based on 100 parts by weight of the prepared epoxy resin solids. After impregnating the varnish to the prepared varnish to apply a varnish to a predetermined thickness, and dried for 1 hour at room temperature, and dried for 4 minutes in an oven at 140 ℃ to prepare a prepreg. Four prepared prepregs were laminated, and copper foil was laminated on the outer surface, and pressure was applied at 5 atmospheres at 180 ° C. for 90 minutes to prepare a copper foil laminate.

Example  2: epoxy compound and copper foil according to the present invention Laminate  Produce

2-1: Epoxy Compound Synthesis

Into a flask equipped with a reflux condenser, 800 g of epichlorohydrin, 340 g of isopropyl alcohol, 135 g of aminophenol, and 120 g of salicylic aldehyde were added, followed by stirring at 30 ° C. for 4 hours to react the aminophenol and salicylic aldehyde. 27 g of% potassium hydroxide aqueous solution was added dropwise at 35 ° C. for 30 minutes, and preliminary reaction was performed at the same temperature for 4 hours. After completion of the preliminary reaction, 90 g of 50 wt% sodium hydroxide was added dropwise at 60 ° C. for 90 minutes, followed by a aging reaction for 30 minutes, followed by washing with distilled water sufficiently to remove the salt twice in the same process. The reaction product from which the salt was removed was decompressed at 155 ° C. for 2 hours to recover unreacted epichlorohydrin and isopropyl alcohol. 860 g of methyl isobutyl ketone was added to the reaction product from which epichlorohydrin and isopropyl alcohol were recovered. The reactant was dissolved, distilled water was added to remove salt through water separation, and then purified by adding 50 wt% sodium hydroxide. Phosphoric acid was added to neutralize the purified reaction product, and the mixture was decompressed at 155 ° C for 3 hours to recover methyl isobutyl ketone, thereby obtaining 240 g of an epoxy compound (yield 70%). Gel permeation chromatography of the epoxy compound thus obtained (Waters 815 pump, 715 Injector, 2414 RI detector) and FT-IR (PerkinElmer's Spectrum10) are shown in FIGS. 3 and 4.

As shown in FIG. 3, the epoxy compound prepared by the above method had a mass average molecular weight of 1,319 g / mol, a molecular weight distribution of 2.6, an epoxy equivalent of 191.3 g / eq, and a hydrolyzable chlorine content of 0.1 wt%. In addition, as shown in Figure 4, the FT-IR analysis, it was able to confirm the characteristic peak of the Ar-OC bond formed by the reaction of the nitrogen-based compound and epichlorohydrin and the characteristic peak of the epoxy ring (FT-IR analysis results ^{: Ar-OC: 1240㎝ -1 &} 1040㎝ -1, Epoxy ring: 911㎝ - & 818㎝ -1).

2-2: copper foil Laminate  Produce

The compound prepared in Example 2 was dissolved in methyl ethyl ketone at 70 wt% of nonvolatile matter, and then dicyandiamide was used as a curing agent in an amount of 3 parts by weight based on 100 parts by weight of the epoxy resin solids, and 2-methyl-imide as a curing accelerator. The varnish was prepared by mixing the dazoles in an amount of 0.14 parts by weight based on 100 parts by weight of the prepared epoxy resin solids. After impregnating the varnish to the prepared varnish to apply a varnish to a predetermined thickness, and dried for 1 hour at room temperature, and dried for 4 minutes in an oven at 140 ℃ to prepare a prepreg. Four prepared prepregs were laminated, and copper foil was laminated on the outer surface, and pressure was applied at 5 atmospheres at 180 ° C. for 90 minutes to prepare a copper foil laminate.

Example  3: epoxy compound and copper foil according to the present invention Laminate  Produce

The epoxy compound prepared in Example 1-1 and the phosphorus non-halogen-based phenol novolak epoxy resin (phosphorus content = 2.8 wt%) were mixed at a ratio of 6: 4 to prepare a mixed epoxy resin. After dissolving the mixed epoxy resin prepared in methyl ethyl ketone at 70 wt% of non-volatile content, dicyan diamide was used as a curing agent in an amount of 3 parts by weight based on 100 parts by weight of the epoxy resin solids, and 2-methyl imidazole was used as a curing accelerator. The varnish was prepared by mixing 0.14 parts by weight based on 100 parts by weight of the prepared epoxy resin solids. The varnish was treated by impregnating glass varnish to apply the varnish to a predetermined thickness, and then dried at room temperature for 1 hour and dried at 140 ° C. for 4 minutes to prepare a prepreg. Four prepared prepregs were laminated, and copper foil was laminated on the outer surface, and pressure was applied at 5 atmospheres at 180 ° C. for 90 minutes to prepare a copper foil laminate.

Comparative Example : Manufacture of conventional nitrogen-based epoxy compound

1250 g of epichlorohydrin and 250 g of aminophenol were added to a flask equipped with a reflux condenser, and then 14 g of a 50 wt% sodium hydroxide aqueous solution was added at 60 ° C., and a preliminary reaction was performed at the same temperature for 4 hours. After completion of the preliminary reaction, 330 g of 50 wt.% Sodium hydroxide was added dropwise at 60 ° C. under reduced pressure to 150 torr for 4 hours. After completion of the dropwise addition, the temperature was raised to 155 ° C to recover unreacted epichlorohydrin for 2 hours. An exotherm occurred at 170 ° C. during the recovery of the unreacted epichlorohydrin, and gelation occurred due to a rapid viscosity increase, and further progress was impossible.

Experimental Example : Characterization

(1) Softening point: It measured by JISK-7234 method.

(2) Epoxy equivalent: It measured by JIS K-7236 method. The unit is g / eq.

(3) Hydrolyzable chlorine concentration: As the 1N KOH ethanol solution was added to the dioxane solution of the sample and refluxed for 30 minutes, the amount of free chlorine was measured by titration of silver nitrate and divided by the weight of the sample.

(4) Flame retardancy analysis: measured by ASTM D3801-87 method.

(5) Thermal Properties: Glass transition temperature was measured by using DSC (Differential Scanning Calorimetry).

(6) Stability Evaluation: The softening point and the weight average molecular weight of the compound were measured by maintaining the mixture at 175 ° C. for 24 hours.

Item Example 1 Example 2 Example 3 Comparative Example 1 Epoxy equivalent weight (g / eq) 181.3 191.25 225 Not measurable Weight average molecular weight (g / mol) 1,111 1,319 1,615 Not measurable Softening point (℃) Semi-solid Semi-solid 62.5 Not measurable Hydrolyzed Chlorine Concentration (ppm) 0.06 0.1 0.04 Not measurable yield(%) 92 70 100 Not measurable Nitrogen content (%) 3.7 3.6 2.2 Not measurable Flammability (UL-94) V-1 V-1 V-0 Not measurable Glass transition temperature (캜) 143.9 136.6 141.3 Not measurable

As shown in Table 1, Comparative Example 1 was confirmed that the gelation proceeds during the synthesis is not possible, while the compounds of the Example was obtained in a yield of 70% or more, in particular, Example 1 was obtained in a yield of 90% or more, Flame retardant also showed that the flame retardancy of UL-94 V-1 grade. In addition, when mixed with the existing flame-retardant epoxy resin as in Example 3, the flame retardancy can be improved to the UL-94 V-0 grade, the glass transition temperature is also 141.3 ℃ to exhibit excellent flame retardancy without significant change in glass transition temperature I could see that.

division 0 hours 6 hours 12 hours 24 hours Example 2 Weight average molecular weight (g / mol) 1,319 1,325 1,337 1,341

As shown in Table 2, when the storage stability at high temperature was measured for Example 2, which has a relatively high molecular weight and more unstable stability at high temperature, it was found that the weight average molecular weight hardly changed with time. Thus, the epoxy compound according to the present invention is excellent in high temperature storage stability and can be usefully used as a blending component of all electrical and electronic materials such as insulating materials, laminates, encapsulation materials, and the like.

It will be understood by those skilled in the art that various changes in form and details may be made therein without departing from the spirit and scope of the invention as defined by the appended claims.

Claims (7)

Epoxy compound represented by the following formula (1):
[Chemical Formula 1]

In Formula 1, n is an integer of 1 to 10.
The epoxy compound according to claim 1, wherein the epoxy compound has an epoxy equivalent of 120 g / eq to 360 g / eq.
The epoxy compound according to claim 1, wherein the epoxy compound has a weight average molecular weight of 300 g / mol to 6,000 g / mol.
A process for preparing an epoxy compound represented by Formula 1, comprising the following steps:
(a) condensing a compound represented by Formula 2 with an aminophenol to produce a compound represented by Formula 3; And
(b) preparing an epoxy compound represented by Chemical Formula 1 by epoxidizing the compound represented by Chemical Formula 3 with an epihalohydrin compound:
[Chemical Formula 1]

In Formula 1, n is an integer of 1 to 10,

(2)

(3)

.
According to claim 4, wherein the step (a) is a method for producing an epoxy compound, characterized in that performed for 3 to 5 hours at 20 ~ 40 ℃.
An epoxy resin composition comprising an epoxy compound represented by the formula (1) and a curing agent:
[Chemical Formula 1]

In Formula 1, n is an integer of 1 to 10.
The epoxy resin composition of claim 6, wherein the curing agent is at least one curing agent selected from the group consisting of a phenolic curing agent, an amine curing agent, and an acid anhydride curing agent.

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