KR20220138144A - Novel acid anhydride-based epoxy compound, epoxy resin composition containing the same, and cured product prepared therefrom - Google Patents

Abstract

The present invention provides an acid anhydride-based epoxy compound, an epoxy resin composition including the same, and a cured product thereof, and the epoxy resin composition of the present invention includes the acid anhydride-based epoxy compound and thus has improved mechanical properties. Since the acid anhydride-based epoxy compound of the present invention directly participates in the curing reaction, phase separation does not occur when an external impact is applied, and the mechanical properties of the cured product as a whole can be improved.

Description

An acid anhydride-based epoxy compound, an epoxy resin composition comprising the same, and a cured product prepared therefrom

The present invention relates to a novel acid anhydride-based epoxy compound, an epoxy resin composition comprising the same, and a cured product prepared therefrom.

Epoxy resins have excellent heat resistance, mechanical properties, electrical properties and adhesion. Due to the characteristics of such an epoxy resin, it is used for sealing materials such as wiring boards, circuit boards, circuit boards in which they are multilayered, semiconductor chips, coils, and electric circuits. Epoxy resins are also used as resins for adhesives, paints, and fiber-reinforced resins.

As such, epoxy resins can be used in a wide range, depending on their reactivity if required for a particular application.

That is, the epoxy resin may be solid, liquid, or semi-solid, and may have various reactivity depending on the application to which they are applied. The reactivity of an epoxy resin is mostly measured in terms of epoxy equivalent, which is the molecular weight of a resin containing a single reactive epoxy group, and the lower the epoxy equivalent, the higher the reactivity of the epoxy resin.

However, epoxy resins are too brittle on their own, which limits their application to some extent. Therefore, to improve the toughness of the epoxy resin, rubber components (e.g., carboxyl-terminated poly(butadiene co-acrylonitrile) (CTBN), amine-terminated poly(butadiene co-acrylonitrile) (ATBN))) , inorganic hard particles (e.g. aluminum trihydrate, glass beads), and high-performance thermoplastic polymers (e.g. polyethersulfone (PES), polyetherimide (PEI), polyetherketone (PEK), polyphenylene oxide (PPO)) ) and the like as an additive for epoxy resins have been studied.

However, an epoxy resin composition having still satisfactory physical properties was not obtained, and thus, an epoxy resin additive capable of achieving the same level or higher physical properties as that of a conventional epoxy resin is required.

KR 10-2020-0027716 A (2020.03.13)

The present invention provides an acid anhydride-based epoxy compound prepared from a novel acid anhydride-based compound.

The present invention also provides an epoxy resin composition comprising the acid anhydride-based epoxy compound of the present invention and a cured product thereof.

To overcome the above problems, the present inventors have continuously studied to develop an epoxy resin composition having excellent mechanical strength such as impact strength and flexural strength due to excellent toughness and a cured product thereof. In the case of an epoxy resin composition containing an anhydride-based epoxy compound, the invention was completed by discovering that it has excellent compatibility with the epoxy base, no phase separation, and excellent toughness, such as impact strength and flexural strength.

The present invention provides an acid anhydride-based epoxy compound represented by the following formula (1).

[Formula 1]

(In Formula 1,

R ₁ to R ₆ are each independently hydrogen or C ₁ -C ₁₀ alkyl;

R ₁ and R ₂ are not simultaneously hydrogen;

Y is hydrocarbylene or heterohydrocarbylene.)

Preferably, in Formula 1 according to an embodiment of the present invention, R ₁ to R ₂ are each independently hydrogen or methyl; R ₃ to R ₆ are each independently hydrogen or C ₁ -C ₇ alkyl; The case where R ₁ and R ₂ are hydrogen at the same time may be excluded.

More preferably, in Formula 1 according to an embodiment of the present invention, Y is C ₅ -C ₆₀ alkylene, C ₃ -C ₆₀ cycloalkylene, C ₆ -C ₆₀ arylene or C ₃ -C ₆₀ heteroarylene ; Alkylene, cycloalkylene, arylene and heteroarylene of Y are hydroxy, halogen, nitrile, nitro, cyano, amino, carboxyl, carboxylate, C ₁ -C ₂₀ alkyl, C ₁ -C ₂₀ alkenyl, C ₁ -C ₂₀ haloalkyl, C ₁ -C ₂₀ alkoxy, C ₁ -C ₂₀ alkoxycarbonyl, C ₃ -C ₃₀ cycloalkyl, C ₆ -C ₃₀ arylC ₁ -C ₂₀ alkyl, C ₆ It may be substituted with one or more selected from -C ₃₀ aryl and C ₃ -C ₃₀ heteroaryl.

More preferably, the acid anhydride-based epoxy compound of Formula 1 according to an embodiment of the present invention may be represented by Formula 2 below in terms of being used as an epoxy resin composition and having more improved physical properties.

[Formula 2]

(In Formula 2,

R ₁ is C ₁ -C ₇ alkyl;

R ₃ to R ₆ are each independently hydrogen or C ₁ -C ₇ alkyl;

Y is hydrocarbylene or heterohydrocarbylene.)

In Formula 2 according to an embodiment of the present invention, Y is C _5-30 alkylene, C ₃ -C ₃₀ cycloalkylene, C ₆ -C ₃₀ arylene or C ₃ -C ₃₀ heteroarylene; Said alkylene, cycloalkylene, arylene and heteroarylene are hydroxy, halogen, nitrile, nitro, cyano, amino, carboxyl, carboxylate, C ₁ -C ₁₀ alkyl, C ₁ -C ₁₀ alkenyl , C ₁ -C ₁₀ haloalkyl, C ₁ -C ₁₀ alkoxy, C ₁ -C ₁₀ alkoxycarbonyl, C ₃ -C ₂₀ cycloalkyl, C ₆ -C ₂₀ ArC ₁ -C ₁₀ alkyl, C ₆ -C It may be substituted with one or more selected from ₂₀ aryl and C ₃ -C ₂₀ heteroaryl groups.

More preferably, Chemical Formula 1 according to an embodiment of the present invention may be represented by Chemical Formulas 3 to 4 below.

[Formula 3]

[Formula 4]

(In Formulas 3 to 4,

R ₁ is a C ₁ -C ₇ alkyl group;

A is -CO-, -SO-, -SO ₂ - or -C(R ₁₁ )(R ₁₂ )-, R ₁₁ to R ₁₂ are each independently hydrogen, C ₁ -C ₇ alkyl, C ₁ -C ₇ haloalkyl or C ₆ -C ₁₂ aryl or R ₁₁ to R ₁₂ may be linked to each other to form a C ₃ -C ₁₀ alicyclic ring;

n is an integer from 1 to 10.)

In addition, the present invention provides an epoxy resin composition comprising an acid anhydride-based epoxy compound represented by Formula 1 above.

The acid anhydride-based epoxy compound according to an embodiment of the present invention may be used as a main agent or a toughening agent.

The epoxy resin composition according to an embodiment of the present invention may further include a base epoxy resin, a curing agent, and a curing accelerator, and the base epoxy resin and the acid anhydride-based epoxy compound may be included in a molar ratio of 1 to 9: 9 to 1 .

The present invention also provides a cured product of the epoxy resin composition of the present invention.

In addition, the present invention provides an acid anhydride-based compound represented by the following formula (5).

[Formula 5]

(In Formula 5,

R is hydrogen, an alkali metal or an alkaline earth metal;

R ₂₁ to R ₂₆ are each independently hydrogen or C ₁ -C ₁₀ alkyl;

Except when R ₂₁ and R ₂₂ are hydrogen at the same time.)

Since the acid anhydride-based epoxy compound of the present invention participates directly in the curing reaction, phase separation does not occur when an impact is applied from the outside, and the mechanical properties of the cured product can be improved as a whole.

Therefore, the epoxy resin composition including the same can provide a cured product having excellent impact strength and flexural strength, and by preventing structural deformation due to external impact, it is possible to implement remarkably improved durability compared to the existing epoxy composition.

Accordingly, the epoxy resin composition employing the acid anhydride-based epoxy compound of the present invention has desired mechanical properties by supplementing the brittleness of conventional epoxy resins, so that various products can be used as adhesives, coatings, paints, and the like. Specifically, it is possible to improve the impact strength and flexural strength of the product by adding it to the lightweight dissimilar material adhesive and coating composition for automobiles.

In addition, the epoxy resin composition comprising the acid anhydride-based epoxy compound of the present invention can be usefully used as a functional adhesive and coating agent in aircraft, spacecraft, railway, ship, sports equipment and computer industries, and The cargo has excellent physical properties.

1 is a graph showing Fourier Transform-Infrared spectroscopy (FT-IR) results of acid anhydride-based epoxy compounds prepared in Examples 2 to 4 of the present invention.

Hereinafter, an acid anhydride-based compound, an acid anhydride-based epoxy compound, an epoxy resin composition comprising the same, and a cured product thereof of the present invention will be described in detail. At this time, unless there are other definitions in the technical terms and scientific terms used, it has the meaning commonly understood by those of ordinary skill in the technical field to which this invention belongs, and in the following description, it may unnecessarily obscure the subject matter of the present invention. Descriptions of possible known functions and configurations will be omitted.

The singular form used in the present invention may also be intended to include the plural form unless the context dictates otherwise.

In addition, in the present invention, the unit used without special mention is based on weight, for example, the unit of % or ratio means weight % or weight ratio, and unless otherwise defined, weight % is any one component of the entire composition. It means % by weight in the composition.

In addition, the numerical range used in the present invention includes a lower limit and an upper limit and all values within the range, increments logically derived from the form and width of the defined range, all values defined therein, and the upper limit of the numerical range defined in different forms. and all possible combinations of lower limits. Unless otherwise defined in the specification of the present invention, values outside the numerical range that may occur due to experimental errors or rounding of values are also included in the defined numerical range.

As used herein, "comprises" is an open-ended description that has a meaning equivalent to expressions such as "comprises", "contains", "has" or "characterizes", and is an element not listed further; Materials or processes are not excluded.

As used herein, "substituted" means that the hydrogen atom of the moiety being substituted (eg, alkyl, aryl, heteroaryl, heterocycle or cycloalkyl) is replaced by a substituent. In one embodiment, each carbon atom of the group being substituted is unsubstituted by more than two substituents. In another embodiment, each carbon atom of the group being substituted is unsubstituted by more than one substituent. In the case of a keto substituent, the two hydrogen atoms are replaced by an oxygen attached to the carbon by a double bond. Optionally substituted substituents of the present invention include hydroxy, halogen, nitrile, nitro, cyano, amino, carboxyl, carboxylate, C ₁ -C ₁₀ alkyl, C ₁ -C ₁₀ alkenyl, C ₁ -C ₁₀ haloalkyl, C ₁ -C ₁₀ alkoxy, C ₁ -C ₁₀ alkoxycarbonyl, C ₃ -C ₂₀ cycloalkyl, C ₆ -C ₂₀ arylC ₁ -C ₁₀ alkyl , C ₆ -C ₂₀ aryl and C ₃ -C ₂₀ heteroaryl and the like.

As used herein, "hydrocarbon" refers to a chemical group containing only hydrogen and carbon atoms.

As used herein, "hydrocarbylene" or "heterohydrocarbylene" refers to a radical having two bonding positions derived from hydrocarbon or heterohydrocarbon, and the meaning of hetero is that carbon is B, O, N, C (=O), P, P(=O), S, S(=O) ₂ and Si means substituted with one or more heteroatoms selected from atoms.

As used herein, "alicyclic ring" is cycloalkyl, which means a non-aromatic monocyclic or multicyclic ring system having 3 to 10 carbon atoms, a 3 to 10 membered ring, preferably 5 It may be a 7-membered ring, and may have an unsaturated bond in the ring.

As used herein, "alkyl" includes both straight-chain or comminuted forms, and may contain from 1 to 30 carbon atoms, preferably from 1 to 20 carbon atoms. In yet another embodiment, alkyl may have 1 to 10 carbon atoms, preferably 1 to 7 carbon atoms, more preferably 1 to 5 carbon atoms, preferably 1 to 3 carbon atoms.

As used herein, "halogen" and "halo" mean fluorine, chlorine, bromine or iodine.

As used herein, "haloalkyl" means an alkyl group in which one or more hydrogen atoms are each replaced by a halogen atom. For example, haloalkyl is -CF ₃ , -CHF ₂ , -CH ₂ F, -CBr ₃ , -CHBr ₂ , -CH ₂ Br, -CC1 ₃ , -CHC1 ₂ , -CH ₂ CI, -CI ₃ , -CHI ₂ , -CH ₂ I, -CH ₂ -CF ₃ , -CH ₂ -CHF ₂ , -CH ₂ -CH ₂ F, -CH ₂ -CBr ₃ , -CH ₂ -CHBr ₂ , -CH ₂ -CH ₂ Br, -CH ₂ -CC1 ₃ , -CH ₂ -CHC1 ₂ , -CH ₂ -CH ₂ CI, -CH ₂ -CI ₃ , -CH ₂ -CHI ₂ , -CH ₂ -CH ₂ I, and the like include that Alkyl and halogen herein are as defined above.

As used herein, "alkenyl" means a saturated straight-chain or branched acyclic hydrocarbon containing from 2 to 30, preferably from 2 to 20 carbon atoms and at least one carbon-carbon double bond. Representative linear and branched (C2-C10) alkenyls are -vinyl, -allyl, -1-butenyl, -2-butenyl, -isobutylenyl, -1-pentenyl, -2-pentenyl, - 3-methyl-1-butenyl, -2-methyl-2-butenic, -2,3-dimethyl-2-butenyl, -1-hexenyl, -2-hexenyl, -3-hex Cenyl, -1-heptenyl, -2-heptenyl, -3-heptenyl, -1-octenyl, -2-octenyl, -3 octenyl, -1-nonenyl, -2-none nyl, -3-nonenyl, -1-disenyl, -2-disenyl, and -3-disenyl. These alkenyl groups may be optionally substituted.

"Alkoxy" as described in the present invention is -OCH ₃ , -OCH ₂ CH ₃ , -O(CH ₂ ) ₂ CH ₃ , -O(CH ₂ ) ₃ CH ₃ , -O(CH ₂ ) ₄ CH ₃ , -O -O-(alkyl), including (CH ₂ ) ₅ CH ₃ , and the like, wherein alkyl is as defined above.

,

,

도 알릴에 포함된다.As used herein, "aryl" refers to a carbocyclic aromatic group containing 5 to 10 ring atoms. Representative examples include phenyl, tolyl, xylyl, naphthyl, tetrahydronaphthyl, anthracenyl, fluorenyl, indenyl, azulenyl, etc. including, but not limited to. Further, aryl is a carbocyclic aromatic group and group connected by alkylene or alkenylene, or B, O, N, C(=O), P, P(=O), S, S(=O)2 and Si atoms Also included are those connected by one or more heteroatoms selected from. As a specific example,

,

,

Also included in allyl.

As used herein, “cycloalkyl” and “cycloaliphatic ring” refer to a monocyclic or polycyclic saturated ring having carbon and hydrogen atoms and no carbon-carbon multiple bonds. Examples of cycloalkyl groups include, but are not limited to, (C3-C10)cycloalkyl (eg, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and cycloheptyl). Cycloalkyl groups may be optionally substituted. In one embodiment, the cycloalkyl group is a monocyclic or bicyclic ring (ring).

As used herein, "carboxyl" and "carboxy" mean -COOH.

As used herein, "heteroaryl" has at least one heteroatom selected from the group consisting of nitrogen, oxygen and sulfur, and contains 5 to 10 members comprising at least one carbon atom, including mono- and bicyclic ring systems. of an aromatic heterocycle ring. Representative heteroaryls include triazolyl, tetrazolyl, oxadiazolyl, pyridyl, furyl, benzofuranyl, thiophenyl, benzothiophenyl, quinolinyl, pyrrolyl, indolyl, oxazolyl, benzoxazolyl ( benzoxazolyl), imidazolyl, benzimidazolyl, thiazolyl, benzothiazolyl, isoxazolyl, pyrazolyl, isothiazolyl, pyridazinyl, pyrimidinyl, pyrazinyl, tria Zinyl, cinnolinyl, phthalazinyl, quinazolinyl, pyrimidyl, oxetanyl, azepinyl, piperazinyl, morpholinyl, dioxanyl, thietanyl and oxazolyl. Heteroaryl groups can be monocyclic or bicyclic. Heteroaryl may be used interchangeably with the term heteroaryl ring, heteroaryl group, or heteroaromatic, and all of these terms may include an optionally substituted ring.

As used herein, “alkoxycarbonyl” refers to an alkoxy-C(=O)-* radical, where “alkoxy” is as defined above. Examples of such alkoxycarbonyl radicals include, but are not limited to, methoxycarbonyl, ethoxycarbonyl, isopropoxycarbonyl, propoxycarbonyl, butoxycarbonyl, isobutoxycarbonyl, t-butoxycarbonyl, and the like. not limited

As used herein, "arylalkyl" refers to one or more hydrogens of alkyl substituted with aryl, and includes benzyl and the like.

,

,

도 알릴렌에 포함된다.As used herein, “alkylene,” “cycloalkylene,” “arylene,” and “heteroarylene” refer to the removal of one hydrogen from “alkyl,” “cycloalkyl,” “aryl,” and “heteroaryl,” respectively. refers to a divalent organic radical derived by As a specific example,

,

,

Also included in allylene.

As used herein, "hydroxy" means -OH, "nitrile" means -CN, "nitro" means -NO ₂ , "cyano" means -CN, ""Amino" means -NH ₂ , "carboxyl" means -COOH, and "carboxylate" means -COOM. M may be an alkali metal or an earth metal.

As used herein, "alkali metal" is a chemical element other than hydrogen in Group 1 of the periodic table, lithium (Li), sodium (Na), potassium (K), rubidium (Rb), cesium (Cs), francium ( Fr), and "alkaline earth metal" means beryllium (Be), magnesium (Mg), calcium (Ca), strontium (Sr), barium (Ba), and radium (Ra), which are group 2 elements of the periodic table.

As described in the present invention, "epoxy resin" refers to a state that has been scientifically reacted with a curing agent, but is a raw material for an epoxy composition as commonly used in the technical field, and has an epoxy group, so an epoxy compound that can react with the curing agent may include.

In addition, as described in the present invention, "cured product" may be a cured product of an epoxy resin composition in a general sense. In addition, the cured product may include a semi-cured material.

Hereinafter, the present invention will be specifically described.

The present invention provides an acid anhydride-based epoxy compound represented by the following formula (1) for providing an epoxy resin composition with improved durability by having excellent strength against external impact and excellent tensile and flexural strength and a cured product thereof.

[Formula 1]

(In Formula 1,

R ₁ to R ₆ are each independently hydrogen or C _1-10 alkyl;

R ₁ and R ₂ are not simultaneously hydrogen;

Y is hydrocarbylene or heterohydrocarbylene.)

The acid anhydride-based epoxy compound represented by Chemical Formula 1 according to an embodiment of the present invention is included in the epoxy resin composition, thereby effectively improving the toughness compared to the conventional epoxy resin, thereby remarkably improving durability.

In terms of preparing an epoxy resin composition having more improved durability, preferably in Formula 1 according to an embodiment of the present invention, R ₁ to R ₂ may be each independently hydrogen or methyl, and R ₃ to R ₆ are each other It may independently be hydrogen or C _1-7 alkyl, and R ₁ and R ₂ may not be hydrogen at the same time.

More preferably, Y in Formula 1 according to an embodiment of the present invention is C ₅ -C ₆₀ alkylene, C ₃ -C ₆₀ cycloalkylene, C ₆ -C ₆₀ arylene, or C ₃ -C ₆₀ heteroarylene ego;

Alkylene, cycloalkylene, arylene and heteroarylene of Y are hydroxy, halogen, nitrile, nitro, cyano, amino, carboxyl, carboxylate, C ₁ -C ₂₀ alkyl, C ₁ -C ₂₀ alkenyl, C ₁ -C ₂₀ haloalkyl, C ₁ -C ₂₀ alkoxy, C ₁ -C ₂₀ alkoxycarbonyl, C ₃ -C ₃₀ cycloalkyl, C ₆ -C ₃₀ arylC ₁ -C ₂₀ alkyl, C ₆ It may be substituted with one or more selected from -C ₃₀ aryl and C ₃ -C ₃₀ heteroaryl.

More preferably, in Formula 1, Y may be C _6-30 arylene or C _3-30 heteroarylene, and the arylene and heteroarylene are optionally hydroxy, halogen, nitrile, nitro, cyano. , amino, carboxyl, carboxylate, C ₁ -C ₂₀ alkyl, C ₁ -C ₂₀ alkenyl, C ₁ -C ₂₀ haloalkyl, C ₁ -C ₂₀ alkoxy, C ₁ -C ₂₀ alkoxycarbonyl, C ₃ - It may be substituted with one or more selected from C ₃₀ cycloalkyl, C ₆ -C ₃₀ arylC ₁ -C ₂₀ alkyl, C ₆ -C ₃₀ aryl and C ₃ -C ₃₀ heteroaryl.

Formula 1 according to an embodiment of the present invention may be represented by Formula 2 below.

[Formula 2]

(In Formula 2,

R ₁ is C _1-7 alkyl;

R ₃ to R ₆ are each independently hydrogen or C _1-7 alkyl;

Y is hydrocarbylene or heterohydrocarbylene.)

Preferably, in Formula 2 according to an embodiment of the present invention, Y is C _5-30 alkylene, C ₃ -C ₃₀ cycloalkylene, C ₆ -C ₃₀ arylene or C ₃ -C ₃₀ heteroarylene;

Said alkylene, cycloalkylene, arylene and heteroarylene are hydroxy, halogen, nitrile, nitro, cyano, amino, carboxyl, carboxylate, C ₁ -C ₁₀ alkyl, C ₁ -C ₁₀ alkenyl , C ₁ -C ₁₀ haloalkyl, C ₁ -C ₁₀ alkoxy, C ₁ -C ₁₀ alkoxycarbonyl, C ₃ -C ₂₀ cycloalkyl, C ₆ -C ₂₀ arylC ₁ -C ₁₀ alkyl, C ₆ -C ₂₀ aryl and C ₃ -C ₂₀ may be substituted with one or more selected from heteroaryl groups, and more preferably, in Formula 2 according to an embodiment of the present invention, R ₁ may be C ₁ -C ₅ alkyl, R ₃ to R ₆ may be each independently hydrogen or C ₁ -C ₅ alkyl, Y is a substituted or unsubstituted C ₆ -C ₃₀ arylene; or substituted or unsubstituted C ₆ -C ₃₀ arylene, more preferably R ₁ is C ₁ -C ₃ alkyl, more preferably methyl, and R ₃ to R ₆ are each independently hydrogen or may be C ₁ -C ₅ alkyl, Y is substituted or unsubstituted C ₆ -C ₃₀ arylene; Or it may be a substituted or unsubstituted C ₆ -C ₃₀ arylene.

In addition, Y in Formulas 1 and 2 may be an organic group that is a divalent radical derived from an epoxy compound. The epoxy compound has a bifunctional group and may be an aliphatic epoxy compound, an alicyclic epoxy compound, or an aromatic epoxy compound.

Specific examples of the aromatic epoxy compound include bisphenol A diglycidyl ether, bisphenol F diglycidyl ether, bisphenol S diglycidyl ether, brominated bisphenol A diglycidyl ether, brominated bisphenol F diglycidyl ether, brominated bisphenol S diglycidyl ether, novolak-type epoxy resins (for example, phenol-novolak-type epoxy resins, cresol-novolak-type epoxy resins, brominated phenol-novolac-type epoxy resins), etc., and alicyclic Specific examples of the epoxy compound may be hydrogenated bisphenol A diglycidyl ether, hydrogenated bisphenol F diglycidyl ether, hydrogenated bisphenol S diglycidyl ether, etc., as an example of an aliphatic epoxy resin, pentaerythritol polyglycidyl ether Cidyl ether, 1,6-hexanediol diglycidyl ether, hexahydrophthalic acid diglycidyl ester, neopentyl glycol diglycidyl ether, trimethylolpropane polyglycidyl ether, 2,2-bis ( 3-glycidyl-4-glycidyloxyphenyl) propane, dimethyloltricyclodecanediglycidyl ether, and the like, but are not limited thereto.

Preferably, Y in Formulas 1 and 2 according to an embodiment of the present invention may be an aromatic epoxy resin, and preferred examples thereof include bisphenol A-based, bisphenol AF-based, bisphenol AP-based, bisphenol B-based, bisphenol C-based, and bisphenol E. Any one or more bisphenol type epoxy compounds selected from, bisphenol F type, bisphenol G type, bisphenol M type, bisphenol S type, bisphenol P type, bisphenol Z type, etc., phenol novolak type epoxy compound, cresol novolak type epoxy compound, etc. Any one or a mixture of two or more may be selected. Preferably, it may be selected from a bisphenol A-based epoxy compound, a bisphenol F-based epoxy compound, and a bisphenol S-based epoxy compound in terms of maximally improving adhesive performance, flexural strength and impact strength.

More preferably, the acid anhydride-based epoxy compound according to an embodiment of the present invention may be represented by the following Chemical Formula 3 or 4.

[Formula 3]

[Formula 4]

(In Formulas 3 to 4,

R ₁ is C ₁ -C ₇ alkyl;

A is -CO-, -SO-, -SO ₂ - or -C(R ₁₁ )(R ₁₂ )-, R ₁₁ to R ₁₂ are each independently hydrogen, C ₁ -C ₇ alkyl, C ₁ -C ₇ haloalkyl or C ₆ -C ₁₂ aryl or R ₁₁ to R ₁₂ may be linked to each other to form a C ₃ -C ₁₀ alicyclic ring;

n is an integer from 1 to 10.)

In Formulas 3 to 4 according to an embodiment of the present invention, R ₁ is C ₁ -C ₅ alkyl; A is -SO ₂ - or -C(R ₁₁ )(R ₁₂ )-, R ₁₁ to R ₁₂ are independently of each other hydrogen, C ₁ -C ₇ alkyl, C ₁ -C ₇ haloalkyl or C ₆ -C ₁₂ aryl or R ₁₁ to R ₁₂ may be linked to each other to form a C ₃ -C ₁₀ alicyclic ring; n may be an integer from 1 to 10, preferably R ₁ is C ₁ -C ₃ alkyl; A is -SO ₂ - or -C(R ₁₁ )(R ₁₂ )-, R ₁₁ to R ₁₂ are independently of each other hydrogen, C ₁ -C ₇ alkyl or C ₁ -C ₇ haloalkyl, or R ₁₁ to R ₁₂ may be linked to each other to form a C ₃ -C ₁₀ alicyclic ring; n may be an integer from 1 to 5.

The acid anhydride-based epoxy compound of Chemical Formulas 3 to 4 according to an embodiment of the present invention may be selected from the following structures, but is not limited thereto.

(In the compound, R ₁ , A and n are the same as defined in Formulas 3 to 4 above.)

The epoxy equivalent weight of the acid anhydride-based epoxy compound according to an embodiment of the present invention may be 200 to 400 g/eq. Specifically, it may satisfy the range of 250 to 350 g/eq., and when an acid anhydride-based epoxy compound satisfying the above range is used, mechanical properties such as impact strength and flexural strength of the epoxy resin composition can be further improved. good to have

In addition, the present invention provides an epoxy resin composition comprising an acid anhydride-based epoxy compound represented by Formula 1 above.

The epoxy resin composition of the present invention includes an acid anhydride-based epoxy compound represented by Formula 1 of the present invention having a specific structure, thereby effectively improving toughness compared to conventional epoxy resins, and thus durability is surprisingly improved.

The epoxy resin composition of the present invention may further include a base epoxy resin, a curing agent, and a curing accelerator.

The epoxy resin composition according to an embodiment of the present invention may be a curable epoxy resin composition, specifically, may be an active energy ray curing type, moisture curing type, thermosetting type or room temperature curing type, etc., preferably a thermosetting type. The thermal curing process can achieve the physical properties described in the present invention by appropriately designing and changing the temperature and time according to the constituent components of the epoxy resin composition and its content. Specifically, it may be thermally cured at a temperature of 80 to 250°C, or thermally cured at a temperature of 100 to 200°C for 3 hours or more, or at 120°C for 1 hour, at 150°C for 1 hour, at 180°C for 1 hour. The thermal curing process may be performed sequentially.

The epoxy resin composition according to an embodiment of the present invention may further include a base epoxy resin, a curing agent, and a curing accelerator.

The base epoxy resin may be a main component of the epoxy resin composition. The base epoxy resin has two or more epoxy groups in the molecule, and may be one selected from saturated, unsaturated, cyclic or acyclic, aliphatic, alicyclic, aromatic and heterocyclic polyepoxy compounds, but a conventional epoxy As long as it is used as the subject of the composition, it may be used without particular limitation. Specifically, it may be any one or a mixture of two or more selected from bisphenol-type epoxy resins, glycytyl ether-based epoxy resins, glycytyl amine-based epoxy resins, phenol novolak-type epoxy resins, and cresol novolak-type epoxy resins, Preferably, it may be any one or a mixture of two or more selected from a bisphenol-type epoxy resin, more preferably a bisphenol A-based epoxy resin, a bisphenol F-based epoxy resin, and a bisphenol S-based epoxy resin.

In addition, the base epoxy resin may be liquid at room temperature, and may have an epoxy equivalent weight of 100 to 600 g/eq, or 150 to 550 g/eq. When used in combination with an acid anhydride-based epoxy compound by satisfying the above range, mechanical properties such as impact strength and flexural strength of the epoxy resin composition can be further improved.

The base epoxy resin and the acid anhydride-based epoxy compound according to an embodiment of the present invention may be included in a molar ratio of 9 to 1: 1 to 9, preferably 7 to 3: 9 to 1, more preferably 8 to 2: It may be 9 to 1, and when the above range is satisfied, the epoxy resin composition of the present invention has a more improved curing behavior and can be easily cured, and external impact by exhibiting superior tensile strength, impact strength and flexural strength By preventing the structural deformation caused by the epoxy composition, it is possible to compensate for insufficient toughness, which is a disadvantage of the conventional epoxy composition, and to express more excellent durability.

The curing agent according to an embodiment of the present invention is not particularly limited as long as it is a compound capable of a curing reaction with an epoxy resin, and a curing agent commonly used may be appropriately selected and used, for example, an acid anhydride curing agent, a phenol-based curing agent, and an amino-based curing agent. It may be selected from the like. The curing agent may be used alone or in combination.

Examples of the acid anhydride-based curing agent include phthalic anhydride, maleic anhydride, trimellitic anhydride, pyromellitic anhydride, hexahydrophthalic anhydride, tetrahydrophthalic anhydride, methylnadic anhydride, nadic anhydride, glutaric anhydride, and any one or two or more selected from methylhexahydrophthalic anhydride and methyltetrahydrophthalic anhydride, but is not limited thereto.

An example of the phenol-based curing agent is phenol such as formaldehyde condensed resol phenol resin, non-formaldehyde condensed phenol resin, novolak-type phenol resin, novolac-type phenol formaldehyde resin, and polyhydroxystyrene resin. Suzy; resol-type phenolic resins such as aniline-modified resol resins and melamine-modified resol resins; novolac-type phenolic resins such as phenol novolac resins, cresol novolac resins, tert-butylphenol novolac resins, nonylphenol novolac resins and naphthol novolac resins; special phenolic resins such as dicyclopentadiene-modified phenolic resins, terpene-modified phenolic resins, triphenolmethane-type resins, phenolaralkyl resins having a phenylene skeleton or diphenylene skeleton, and naphtholaralkyl resins; and any one or two or more selected from a polyhydroxystyrene resin such as poly(p-hydroxystyrene), but is not limited thereto.

Examples of the amino curing agent include dimethyl dicykan (DMDC), dicyandiamide (DICY), isophoronediamine (IPDA), diethylenetriamine (DETA), triethylenetetramine (TETA), bis( p-aminocyclohexyl)methane (PACM), methylenedianiline (eg 4,4′-methylenedianiline), polyetheramines such as polyetheramine D230, diaminodiphenylmethane (DDM), Diaminodiphenylsulfone (DDS), 2,4-toluenediamine, 2,6-toluenediamine, 2,4-diamino-1-methylcyclohexane, 2,6-diamino-1-methylcyclohexane, 2 ,4-diamino-3,5-diethyltoluene, 2,6-diamino-3,5-diethyltoluene, 1,2-diaminobenzene, 1,3-diaminobenzene, 1,4-dia minobenzene, diaminodiphenyl oxide, 3,3',5,5'-tetramethyl-4,4'-diaminobiphenyl and 3,3'-dimethyl-4,4'-diaminodiphenyl, etc. Any one or two or more may be selected, but the present invention is not limited thereto.

In addition, the curing agent according to an embodiment of the present invention has a ratio of the active hydrogen equivalent weight (AHEW) of the curing agent to the total epoxy equivalent weight (EEW) of the acid anhydride-based epoxy compound included in the epoxy resin composition of the present invention: 1:0.8 to 1.5, preferably 1: it may be preferable to set the content of the curing agent so as to satisfy 0.9 to 1.2.

The curing accelerator according to an embodiment of the present invention is for controlling the curing rate, and may be selected from an imidazole-based accelerator and a urea-based accelerator. The curing accelerator may be used alone or in combination.

Examples of the imidazole accelerator include 2-methyl imidazole, 2-heptadecyl imidazole, 2-phenyl imidazole, 1-benzyl-2-methylimidazole, 1-benzyl-2-phenylimidazole, 2-Ethyl-4-methylimidazole, 2-methylimidazole, 2,4-diamino-6-[2'-methylimidazolyl-(1')]-ethyl-s-triazine, 2 ,4-diamino-6-[2'-undecylimidazolyl-(1')]-ethyl-s-triazine, 2-undecylimidazole, 3-heptadecylimidazole, 2-phenyl imidazole, 2-phenylimidazoline, 1,2-dimethylimidazole, 1-cyanoethyl-2-methylimidazole, 1-cyanoethyl-2-ethyl-4-methylimidazole and One or two or more selected from 1-cyanoethyl-2-undecylimidazole and the like may be mentioned, but the present invention is not limited thereto.

As an example of the urea-based accelerator, any one selected from p-chlorophenyl-N,N-dimethylurea, 3-phenyl-1,1-dimethylurea and 3,4-dichlorophenyl-N,N-dimethylurea or the like Two or more may be mentioned, but are not limited thereto.

In addition, the curing accelerator may include 0.01 to 5 parts by weight, preferably 0.01 to 2 parts by weight, based on 100 parts by weight of the sum of the base epoxy resin and the acid anhydride-based epoxy compound included in the epoxy resin composition, but limited thereto it's not going to be

In addition to this, one or more other additives may be optionally added to the epoxy resin composition according to an embodiment of the present invention. For example, the additives include inorganic fillers, stabilizers, viscosity modifiers, surfactants, pigments or dyes, matting agents, flame retardants, curing inhibitors, defoamers, wetting agents, colorants, thermoplastics, processing aids, ultraviolet (UV) blockers, fluorescent compounds. , a UV stabilizer, an antioxidant, a mold release agent, and mixtures thereof. The additive may be used in a range that does not impair the physical properties of the resin composition of the present invention. The epoxy resin composition according to an embodiment of the present invention may be used for coating, paint, adhesion, insulator, and the like, and preferably for coating or adhesion.

In addition, the present invention may provide a cured product of the epoxy resin composition according to an embodiment of the present invention.

The cured product according to an embodiment of the present invention can satisfy the impact strength of 60 J/m or more, preferably 70 J/m or more, when the base epoxy resin and the acid anhydride-based epoxy compound are included in a molar ratio of 8:2. have. It has an improved impact strength of 1.5 times or more, or 1.7 times or more, or 1.9 times or more compared to the case where the acid anhydride-based epoxy compound is not included.

The cured product according to an embodiment of the present invention may have a flexural strength of 120 MPa or more or 130 MPa or more when the base epoxy resin and the acid anhydride-based epoxy compound are included in a molar ratio of 9:1.

In addition, the present invention to provide an acid anhydride-based compound for the preparation of the acid anhydride-based epoxy compound of the present invention, the acid anhydride-based compound of the present invention may be represented by the following formula (5).

[Formula 5]

(In Formula 5,

R is hydrogen, an alkali metal or an alkaline earth metal;

R ₂₁ to R ₂₆ are each independently hydrogen or C ₁ -C ₁₀ alkyl;

Except when R ₂₁ and R ₂₂ are hydrogen at the same time.)

Preferably, in Formula 5 according to an embodiment of the present invention, R is hydrogen or an alkali metal; R ₂₁ to R ₂₆ are each independently hydrogen or C ₁ -C ₅ alkyl; R ₂₁ and R ₂₂ may be excluded when they are hydrogen at the same time, more preferably R is hydrogen; R ₂₁ to R ₂₆ are each independently hydrogen or C ₁ -C ₃ alkyl; R ₂₁ and R ₂₂ may be excluded when they are hydrogen at the same time.

Specifically, the acid anhydride-based compound according to an embodiment of the present invention may be selected from the following compounds, but is not limited thereto.

The acid anhydride-based epoxy compound according to an embodiment of the present invention can be prepared by any method that can be recognized by those skilled in the art, but for example, an acid anhydride-based compound is prepared from an acid anhydride and glycidol as in Scheme 1 below, and the It can be prepared by reacting with an epoxy resin again.

[Scheme 1]

(Y, R ₁ to R ₆ in Scheme 1 are the same as defined in Formula 1.)

Hereinafter, an epoxy resin composition comprising an acid 　 anhydride-based epoxy compound according to the present invention will be described in more detail through Examples. However, the following examples are only a reference for describing the present invention in detail, and the present invention is not limited thereto, and may be implemented in various forms. Also, unless otherwise defined, all technical and scientific terms have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs. In addition, the terminology used in the description in the present invention is only for effectively describing specific embodiments, and is not intended to limit the present invention.

[Assessment Methods]

1. Epoxy equivalent weight [g/eq.]

Epoxy equivalent weight was measured according to ASTM D1652-04.

2. Impact strength [J/m]

Impact strength was measured according to ASTM D 256 standard using an Izod-type impact tester (JJHBT-6501, JJ-test).

3. Tensile strength [MPa]

It was measured using a universal testing machine (UTM 5982, INSTRON), and the test was performed according to ASTM D 638 standard.

4. Flexural strength [MPa]

Flexural strength was measured according to ASTM D7264M using a universal testing machine (UTM 5982, INSTRON).

5. Hardening behavior

It was measured using a differential scanning calorimeter (DSC Q2000, TA instruments), and the temperature increase test was analyzed at a temperature increase rate of 10 °C/min in a temperature range of -80 to 250 °C.

[Example 1] Preparation of acid anhydride-based compound (MHPA-ME)

　　　　

After putting 158.0 g (0.76 mol) of 4-methylhexahydrophthalic anhydride (4-MHHPA) and 59.0 g (0.76 mol) of glycidol in a round flask, the reaction mixture was stirred at 60° C. for 3 hours. was sampled, and the reaction was terminated at the point where the epoxy equivalent weight became 242.27 g/eq. according to ASTM D1652 to prepare a compound MHPA-ME.

The MHPA-ME obtained by the above method was analyzed by FT-IR, and in the FT-IR graph, it was confirmed that 1857cm ^-1 , the peak of the symmetric anhydride, disappeared and the ring of acid anhydride was opened ^. The structure of the title product, MHPA-ME, was confirmed by confirming that an epoxy structure was added to the resulting peak.

[Example 2] Preparation of acid anhydride-based epoxy compound (MHPA-MFE)

In a round flask, bisphenol F diglycidyl ether having an epoxy group at the end and MHPA-ME prepared in Example 1 were added in a molar ratio of 1:1, and the reaction mixture was sampled while stirring at 60° C. for 3 hours, ASTM D1652 The reaction was terminated at the point where the epoxy equivalent weight measured by the method became 302.8 g/eq.

The MHPA-MFE obtained by the above method was analyzed by FT-IR, which is shown in FIG. 1 .

As shown in FIG. 1, it was confirmed that the title compound, MHPA-MFE, was prepared by generating an ester peak and an epoxy peak corresponding to each epoxy of the prepared MHPA-MFE.

[Example 3] Preparation of acid anhydride-based epoxy compound (MHPA-MSE)

An epoxy compound, MHPA-MSE, was prepared in the same manner as in Example 2, except that bisphenol B diglycidyl ether was used instead of diglycidyl ether of bisphenol F in Example 2, and in the same manner as in Example 2, FT Analysis via -IR confirmed that the title compound was prepared.

[Example 4] Preparation of epoxy compound (MHPA-MJE)

In Example 2, an epoxy compound, MHPA-MSE, was prepared in the same manner as in Example 2, except that ductile epoxy (Jeil Hwasung Co., Ltd., JRE-320) in the above reaction formula was used instead of bisphenol F diglycidyl ether. , It was confirmed that the title compound was prepared by analysis through FT-IR as in Example 2.

[Example 5]

The composition shown in Table 1 was added to a planetary mixer and stirred at room temperature for 30 minutes under vacuum conditions to prepare an epoxy resin composition. A cured product was prepared by sequentially curing the prepared epoxy resin composition using a mold suitable for each test piece in a curing oven at 120° C. for 1 hour, 150° C. for 1 hour, and 180° C. for 1 hour.

Specifically, bisphenol A diglycidyl ether (DGEBA, Momentive, EPIKOTE 828) was used as the base epoxy resin, and the sum of the base epoxy resin and the acid anhydride-based epoxy compound (MTPA-MFE) of Example 2 was 100 Each epoxy resin composition was prepared by adding 10 mol%, 20 mol%, and 25 mol% of an acid anhydride-based epoxy compound to be mol%. Dicyandiamide (DICY) was used as the curing agent, and the curing agent was added by matching the epoxy equivalent weight of the acid anhydride-based epoxy compound included in the composition and the active hydrogen equivalent weight (AHEW) of dicyandiamide in 1:1. The curing accelerator, 2-methylimidazole, was added in an amount of 0.2 parts by weight based on 100 parts by weight of the sum of the base epoxy resin and the acid anhydride-based epoxy compound (MTPA-MFE) of Example 2.

The epoxy composition prepared in each was cured in a curing oven to prepare a cured product, and the cured product prepared as a composition containing 10 mol% of each cured product was MTPA-MFE 10 and a composition containing 20 mol% The prepared cured product was denoted as MTPA-MFE 20, and the cured product prepared with the composition containing 25 mol% was denoted as MTPA-MFE 25.

The prepared cured product was measured for physical properties through the evaluation method described above, and the measured results are shown in Table 2 below.

[Examples 6 to 7]

In Example 5, instead of the acid anhydride-based epoxy compound (MTPA-MFE) of Example 2, the acid anhydride-based epoxy compound prepared in Example 3 (MTPA-MSE) or the acid anhydride-based epoxy compound prepared in Example 4 (MTPA) -MJE) was used to prepare a cured product in the same manner as in Example 5, and the prepared cured product was MTPA-MSE 10, MTPA-MSE 20 according to the content and type of the acid anhydride-based epoxy compound, respectively. , MTPA-MSE 25, MTPA-MJE 10, MTPA-MJE 20, MTPA-MJE 25.

The prepared cured product was measured for physical properties by the evaluation method described above, and the measured results are shown in Table 2 below.

[Comparative Example 1]

A cured product was prepared in the same manner as in Example 5 except that MTPA-MFE, the acid anhydride-based epoxy compound of Example 2 of the present invention, was not added in Example 5.

The prepared cured product was measured for physical properties by the evaluation method described above, and the measured results are shown in Table 2 below.

epoxy compound Bisphenol A diglycidyl ether
(weight%) type content
(weight%) Example 5 MTPA-MFE 10 MTPA-MAE 10 90 MTPA-MFE 20 MTPA-MAE 20 80 MTPA-MFE 25 MTPA-MAE 25 75 Example 6 MTPA-MSE 10 MTPA-MSE 10 90 MTPA-MSE 20 MTPA-MSE 20 80 MTPA-MSE 25 MTPA-MSE 25 75 Example 7 MTPA-MJE 10 MTPA-MJE 10 90 MTPA-MJE 20 MTPA-MJE 20 80 MTPA-MJE 25 MTPA-MJE 25 75 Comparative Example 1 - 100

DSC impact strength
(J/m) The tensile strength
(MPa) flexural strength
(MPa) T _Peak (℃) T _Onset
(℃) Example 5 MTPA-MFE 10 169.55 156.91 74.23 (±5.27) 53.17 (±6.11) 150.6 (±11.1) MTPA-MFE 20 176.75 165.47 81.41 (±5.26) 61.62 (±3.17) 139.1 (±15.8) MTPA-MFE 25 178.24 166.43 67.28 (±5.03) 50.71 (±3.14) 145.1 (±8.0) Example 6 MTPA-MSE 10 172.55 159.05 60.96 (±1.23) 49.81 (±2.74) 138.4 (±3.5) MTPA-MSE 20 177.13 165.62 63.29 (±2.63) 49.38 (±5.58) 145.2 (±4.14) MTPA-MSE 25 178.18 167.21 80.14 (±6.14) 49.79 (±2.11) 131.2 (±8.1) Example 7 MTPA-MJE 10 172.98 159.67 82.28 (±7.37) 59.17 (±4.95) 140.2 (±0.37) MTPA-MJE 20 180.56 168.41 82.45 (±9.22) 57.7 (±1.94) 135.2 (±1.24) MTPA-MJE 25 182.86 169.75 63.2 (±3.11) 54.21 (±6.21) 130.4 (±2.42) Comparative Example 1 153.73 127.23 47.30 (±0.95) 63.69 (±3.54) 108.1 (±1.05)

As shown in Table 2, it can be seen that the epoxy resin composition comprising the acid anhydride-based epoxy compound according to the present invention has not only excellent curing behavior but also improved physical properties in impact strength, tensile strength and flexural strength. .

Specifically, the onset temperature of the epoxy resin compositions containing the acid anhydride-based epoxy compound of the present invention was observed around 155 to 170° C., and it can be seen that the Tpeak also increases as the content of the acid anhydride-based epoxy compound increases. From this, it can be seen that the increase in Tpeak originates from the acid anhydride-based epoxy compound.

Therefore, it can be seen that the epoxy resin composition of the present invention can be used as an epoxy resin composition having more improved physical properties compared to Comparative Example 1.

In addition, the epoxy resin composition of the present invention has more improved physical properties compared to the comparative example in impact strength and flexural strength, and the base epoxy resin and the acid anhydride-based epoxy compound of the present invention are 7.5　 to 2.5　 to 　9 to 　1. It can be seen that when it is included in a molar ratio of 　, especially 　8　:　2, it has extremely excellent physical properties.

Accordingly, the epoxy resin composition containing the acid anhydride-based epoxy compound according to the present invention can provide a cured product having excellent impact strength and flexural strength, and by preventing structural deformation due to external impact, significantly more than the existing epoxy composition It was confirmed that excellent durability can be expressed. In particular, it is possible to improve the impact strength and flexural strength of the product by adding it to the composition of the lightweight dissimilar material adhesion and coating material for automobiles.

As described above, the present invention has been described with specific matters and limited examples and comparative examples, but these are only provided to help a more general understanding of the present invention, and the present invention is not limited to the above examples, and the present invention is not limited to the above examples. Various modifications and variations are possible from these descriptions by those of ordinary skill in the art.

Therefore, the spirit of the present invention should not be limited to the described embodiments, and not only the claims described below, but also all those with equivalent or equivalent modifications to the claims will be said to belong to the scope of the spirit of the present invention. .

Claims (12)

An acid anhydride-based epoxy compound represented by the following formula (1).
[Formula 1]

In Formula 1,
R ₁ to R ₆ are each independently hydrogen or C ₁ -C ₁₀ alkyl;
R ₁ and R ₂ are not simultaneously hydrogen;
Y is hydrocarbylene or heterohydrocarbylene. The method of claim 1,
In Formula 1, R ₁ to R ₂ are each independently hydrogen or methyl;
R ₃ to R ₆ are each independently hydrogen or C ₁ -C ₇ alkyl;
R ₁ and R ₂ are not hydrogen at the same time, an acid anhydride-based epoxy compound. The method of claim 1,
In Formula 1, Y is C ₅ -C ₆₀ alkylene, C ₃ -C ₆₀ cycloalkylene, C ₆ -C ₆₀ arylene, or C ₃ -C ₆₀ heteroarylene;
Alkylene, cycloalkylene, arylene and heteroarylene of Y are hydroxy, halogen, nitrile, nitro, cyano, amino, carboxyl, carboxylate, C ₁ -C ₂₀ alkyl, C ₁ -C ₂₀ alkenyl, C ₁ -C ₂₀ haloalkyl, C ₁ -C ₂₀ alkoxy, C ₁ -C ₂₀ alkoxycarbonyl, C ₃ -C ₃₀ cycloalkyl, C ₆ -C ₃₀ arylC ₁ -C ₂₀ alkyl, C ₆ -C ₃₀ aryl and C ₃ -C ₃₀ It may be further substituted with one or more selected from heteroaryl, acid anhydride-based epoxy compound. The method of claim 1,
The acid anhydride-based epoxy compound of Formula 1 is an acid anhydride-based epoxy compound represented by the following Formula 2.
[Formula 2]

In Formula 2,
R ₁ is C ₁ -C ₇ alkyl;
R ₃ to R ₆ are each independently hydrogen or C ₁ -C ₇ alkyl;
Y is hydrocarbylene or heterohydrocarbylene.) 5. The method of claim 4,
In Formula 2, Y is C _5-30 alkylene, C ₃ -C ₃₀ cycloalkylene, C ₆ -C ₃₀ arylene, or C ₃ -C ₃₀ heteroarylene;
Said alkylene, cycloalkylene, arylene and heteroarylene are hydroxy, halogen, nitrile, nitro, cyano, amino, carboxyl, carboxylate, C ₁ -C ₁₀ alkyl, C ₁ -C ₁₀ alkenyl , C ₁ -C ₁₀ haloalkyl, C ₁ -C ₁₀ alkoxy, C ₁ -C ₁₀ alkoxycarbonyl, C ₃ -C ₂₀ cycloalkyl, C ₆ -C ₂₀ ArC ₁ -C ₁₀ alkyl, C ₆ -C ₂₀ aryl and C ₃ -C ₂₀ Which may be further substituted with one or more selected from a heteroaryl group, an acid anhydride-based epoxy compound. 5. The method of claim 4,
The acid anhydride-based epoxy compound of Formula 2 is an acid anhydride-based epoxy compound represented by the following Chemical Formulas 3 to 4.
[Formula 3]

[Formula 4]

In Formulas 3 to 4,
R ₁ is a C ₁ -C ₇ alkyl group;
A is -CO-, -SO-, -SO ₂ - or -C(R ₁₁ )(R ₁₂ )-, R ₁₁ to R ₁₂ are each independently hydrogen, C ₁ -C ₇ alkyl, C ₁ -C ₇ haloalkyl or C ₆ -C ₁₂ aryl or R ₁₁ to R ₁₂ may be linked to each other to form a C ₃ -C ₁₀ alicyclic ring;
n is an integer from 1 to 10; An epoxy resin composition comprising an acid anhydride-based epoxy compound represented by the following formula (1).
[Formula 1]

In Formula 1,
R ₁ to R ₆ are each independently hydrogen or C ₁ -C ₁₀ alkyl;
R ₁ and R ₂ are not simultaneously hydrogen;
Y is hydrocarbylene or heterohydrocarbylene. 8. The method of claim 7,
The acid anhydride-based epoxy compound is an epoxy resin composition used as a main agent or toughening agent. 8. The method of claim 7,
The epoxy resin composition is an epoxy resin composition further comprising a base epoxy resin, a curing agent and a curing accelerator. 10. The method of claim 9,
The base epoxy resin and the acid anhydride-based epoxy compound is an epoxy resin composition included in a molar ratio of 1 to 9: 9 to 1. A cured product of the epoxy resin composition of any one of claims 7 to 10. An acid anhydride-based compound represented by the following formula (5).
[Formula 5]

In Formula 5,
R is hydrogen, an alkali metal or an alkaline earth metal;
R ₂₁ to R ₂₆ are each independently hydrogen or C ₁ -C ₁₀ alkyl;
Except when R ₂₁ and R ₂₂ are hydrogen at the same time.

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