Composition, curable composition, cured product, sealing material containing composition, conductive material, thermally conductive material, insulating material, adhesive for camera module, structural adhesive, matrix resin for fiber-reinforced plastic, impregnation fixing agent, interlayer insulating film, film-type solder resist, sealing sheet, conductive film, anisotropic conductive film, and thermally conductive film

Abstract

This composition comprises: a component A which is a compound represented by formula (1); and a component B which is a compound represented by formula (2). (In formulae (1) and (2), R1 is one selected from the group consisting of an ethylene group, an n-propylene group, an isopropylene group, and an n-butylene group, and when a plurality of R1s are included, they may be the same as or different from each other. R2 represents a divalent group having a six-membered ring structure. R3 is one selected from the group consisting of an ethylene group, an n-propylene group, an isopropylene group, and an n-butylene group, and when a plurality of R3s are included, they may be the same as or different from each other. Gy represents a glycidyl group. G1 and G2 each represent a glycidyl group or hydrogen. L and M are each independently an integer of 1-15. L and M satisfy 2≤(L+M)≤16. N is an integer of 1-10.)

Description

Compositions, curable compositions, cured products, sealing materials containing compositions, conductive materials, thermally conductive materials, insulating materials, adhesives for camera modules, structural adhesives, matrix resins for fiber-reinforced plastics, impregnation adhesives, interlayer insulating films, film-type solder resists, sealing sheets, conductive films, anisotropic conductive films, and thermally conductive films.

[0001] The present invention relates to compositions, curable compositions, cured products, encapsulants containing compositions, conductive materials, thermally conductive materials, insulating materials, adhesives for camera modules, structural adhesives, matrix resins for fiber-reinforced plastics, impregnation adhesives, interlayer insulating films, film-type solder resists, encapsulation sheets, conductive films, anisotropic conductive films, and thermally conductive films.

[0002] Compositions containing epoxy compounds have traditionally been used in a wide range of applications, including insulating materials, sealing materials, adhesives, conductive materials, matrix resins for fiber-reinforced plastics, impregnation and fixing agents for motor coils, and adhesives for automotive structures.

[0003] For example, Patent Document 1 discloses an epoxy resin with low viscosity and excellent flexibility, adhesion, and low water absorption, as well as an epoxy resin composition containing the same.

[0004] International Publication No. 2014 / 021386

[0005] In recent years, with the increasing size of semiconductor chips, there has been a demand for encapsulation materials that can achieve both crack resistance and adhesion. Therefore, there is a need for compositions containing epoxy compounds that impart excellent flexibility, adhesion, and toughness to encapsulation materials, thereby achieving both crack resistance and strong adhesion, as well as curable compositions containing such compositions. However, the epoxy resin and epoxy resin composition described in Patent Document 1 are not sufficient for application to large semiconductor chips in terms of achieving both crack resistance and strong adhesion, and there is room for improvement.

[0006] Therefore, the present invention aims to provide a composition capable of imparting excellent flexibility, adhesion, and toughness to a cured product, and a curable composition containing the said composition.

[0007] As a result of intensive studies to solve the above-mentioned problems, the present inventors have found that a composition containing a compound having a predetermined constitution can solve the above problems, and have completed the present invention. That is, the present invention is as follows.

[0008] [1] A composition comprising: Component A: a compound represented by the following formula (1); and Component B: a compound represented by the following formula (2).

[0009]

[0010] (In the above formula (1) and formula (2), R １ is one selected from the group consisting of an ethylene group, an n-propylene group, an isopropylene group, and an n-butylene group, and when a plurality of R １ are included, they may be the same or different. R ２ represents a divalent group having a 6-membered ring structure. R ３ is one selected from the group consisting of an ethylene group, an n-propylene group, an isopropylene group, and an n-butylene group, and when a plurality of R ３ are included, they may be the same or different. Gy represents a glycidyl group. G １ and G ２ each represent a glycidyl group or a hydrogen atom. L and M are each independently an integer of 1 to 15. L and M satisfy 2 ≤ (L + M) ≤ 16. N is an integer of 1 to 10.)

[0011] [2] The composition according to [1] above, wherein the component B comprises a compound represented by the following formula (2)-1 and a compound represented by the following formula (2)-2.

[0012]

[0013] (In the above formula (2)-1 and formula (2)-2, R ３ is one selected from the group consisting of an ethylene group, an n-propylene group, an isopropylene group, and an n-butylene group, and when a plurality of R ３ are included, they may be the same or different. Gy represents a glycidyl group. N is an integer of 1 to 10.)

[0014] [3] The composition according to [1] or [2], wherein the mass ratio of the component A to the component B is mass of component A : mass of component B = 50:50 to 99:1. [4] The composition according to any one of [1] to [3], further comprising a component C: a compound represented by the following formula (3).

[0015]

[0016] (In the above formula (3), R １ is one selected from the group consisting of an ethylene group, an n-propylene group, an isopropylene group, and an n-butylene group, and when a plurality of R １ are present, they may be the same or different. R ２ represents a divalent group having a 6-membered ring structure. L and M are each independently an integer of 1 to 15. L and M satisfy 2≦(L+M)≦16.)

[0017] [5] The composition according to any one of [1] to [4], wherein when the Area area of the component A in an MS chart of LC-MS is taken as 100, the Area area of the component B is 0.5 to 17. [6] The composition according to any one of [2] to [5], wherein when the Area area of the component A in an MS chart of LC-MS is taken as 100, the area of the compound with N=7 of the formula (2)-1 is 0.1 to 2.0, and the area of the compound with N=7 of the formula (2)-2 is 0.2 to 3.5. [7] As the component A, R in the formula (1) above １ is an n-propylene group or an isopropylene group, and R ２ comprises a compound having a structure of the following formula (4) or formula (5), and as the component B, R in the formula (2) above ３ comprises a compound in which R is an n-propylene group or an isopropylene group, the composition according to any one of [1] to [4].

[0018]

[0019] [8] As the component A, R in the formula (1) above １ is an n-propylene group or an isopropylene group, and R ２The compound comprises a compound having the structure of formula (4) or formula (5) below, wherein the component B is R in formula (2). ３ The composition according to any one of [5] to [7] above, wherein the compound comprises an n-propylene group or an isopropylene group.

[0020]

[0021] [9] The above-mentioned component B includes the compound shown in formula (2)-1 and the compound shown in formula (2)-2 below,

[0022]

[0023] (In equations (2)-1 and (2)-2 above, R ３ : One selected from the group consisting of ethylene group, n-propylene group, isopropylene group, and n-butylene group, and R when multiple are present. ３ (These may be the same or different. Gy: Indicates a glycidyl group. N: An integer from 1 to 10.)

[0024] Furthermore, the composition according to any one of [1] to [8] above, comprising component C: a compound shown in the following formula (3).

[0025]

[0026] (In the above formula (3), R １ : One selected from the group consisting of ethylene group, n-propylene group, isopropylene group, and n-butylene group, and R when multiple are present. １ They may be the same or different. ２ : Indicates a divalent group having a 6-membered ring structure. L and M are independent integers from 1 to 15. L and M satisfy 2 ≤ (L + M) ≤ 16.

[0027]

[10] The composition according to [9], wherein the content of component C is 0.0001% by mass or more and 2% by mass or less of the total composition.

[11] A curable composition comprising the composition according to any one of [1] to

[10] , and component D: a compound that reacts with the compound of component A shown in formula (1) and the compound of component B shown in formula (2).

[12] The curable composition according to

[11] , wherein component D comprises one or more selected from the group consisting of amine compounds, compounds having a phenol structure, compounds having an acid anhydride structure, compounds having an active ester structure, compounds having a cyanate ester structure, compounds having a thiol group, bismaleimide compounds, benzoxazine compounds, and carbodiimide compounds.

[13] The curable composition according to

[11] or

[12] , further comprising component E: a filler.

[14] A cured product of the curable composition according to

[11] or

[12] .

[15] A cured product of the curable composition described in

[13] .

[16] A sealing material comprising the composition described in any one of [1] to

[10] .

[17] A conductive material comprising the composition described in any one of [1] to

[10] .

[18] A thermally conductive material comprising the composition described in any one of [1] to

[10] .

[19] An insulating material comprising the composition described in any one of [1] to

[10] .

[20] An adhesive for camera modules comprising the composition described in any one of [1] to

[10] .

[21] A structural adhesive comprising the composition described in any one of [1] to

[10] .

[22] A matrix resin for fiber-reinforced plastics comprising the composition described in any one of [1] to

[10] .

[23] An impregnation adhesive comprising the composition described in any one of [1] to

[10] .

[24] An interlayer insulating film comprising the composition described in any one of [1] to

[10] .

[25] A film-type solder resist comprising the composition described in any one of [1] to

[10] above.

[26] A sealing sheet comprising the composition described in any one of [1] to

[10] above.

[27] A conductive film comprising the composition described in any one of [1] to

[10] above.

[28] An anisotropic conductive film comprising the composition described in any one of [1] to

[10] above.

[29] A thermally conductive film comprising the composition described in any one of [1] to

[10] above.

[0028] According to the present invention, it is possible to provide a composition that can impart excellent flexibility, adhesion, and toughness to a cured product, and a curable composition containing the same.

[0029] The following describes in detail embodiments for carrying out the present invention (hereinafter referred to as "this embodiment"). This embodiment is illustrative for explaining the present invention and is not intended to limit the present invention to the following content. The present invention can be implemented by modifying it as appropriate within the scope of its gist.

[0030] In this specification, the structures of the ethylene group, n-propylene group (sometimes called trimethylene group), isopropylene group (sometimes called propylene group), and n-butylene group (sometimes called tetramethylene group), and the structures of their alkylene oxide groups, are as follows. In the following formulas, "*" indicates a bonding site.

[0031]

[0032]

[0033]

[0034]

[0035]

[0036]

[0037]

[0038]

[0039] [Composition] The composition of this embodiment contains: Component A: A compound shown in the following formula (1) (hereinafter sometimes referred to as Component A) and Component B: A compound shown in the following formula (2) (hereinafter sometimes referred to as Component B).

[0040]

[0041] In equations (1) and (2) above, R １ : One selected from the group consisting of ethylene group, n-propylene group, isopropylene group, and n-butylene group, and R when multiple are present. １ They may be the same or different. ２ : Indicates a divalent group having a six-membered ring structure. R ３ : One selected from the group consisting of ethylene group, n-propylene group, isopropylene group, and n-butylene group, and R when multiple are present. ３ They may be the same or different. Gy: Indicates a glycidyl group. G １ G ２ : Represents a glycidyl group or hydrogen. L, M: Each is an integer from 1 to 15, independently of the others. L, M: Satisfy 2 ≤ (L + M) ≤ 16. N: An integer from 1 to 10.

[0042] According to the composition described above, the cured product of a curable composition containing a predetermined compound that is reactive with the composition can be given excellent flexibility, adhesion, and toughness.

[0043] (Component A) The composition of this embodiment contains the compound shown in formula (1) above as component A.

[0044]

[0045] In formula (1) above, R １ R is one selected from the group consisting of an ethylene group, an n-propylene group, an isopropylene group, and an n-butylene group. １ They may be the same or different. From the viewpoint of the toughness of the cured product of this embodiment, which will be described later, R １ It is preferable that the group is selected from the group consisting of n-propylene, isopropylene, and n-butylene groups, and more preferably an n-propylene group or an isopropylene group from the viewpoint of excellent low viscosity.

[0046] Furthermore, in formula (1) above, R ２R is a divalent group having a six-membered ring structure. The six-membered ring structure is not limited to the following, but examples include a cyclohexane structure, a benzene structure, a piperidine structure, a pyridine structure, a tetrahydropyran structure, a pyran structure, etc., and from the viewpoint of industrial handling, the cyclohexane structure and the benzene structure are preferred. ２ From the viewpoint of the mechanical strength of the cured product of this embodiment, which will be described later, it is more preferable that the structure be that of formula (4) or formula (5) below, and from the viewpoint of heat resistance, it is even more preferable that the structure be that of formula (5) below.

[0047]

[0048] In formula (1) above, L and M are each independent integers from 1 to 15, satisfying 2 ≤ (L + M) ≤ 16. When L + M is 2 or more, excellent flexibility can be imparted to the cured product of the curable composition of this embodiment, which will be described later. When L + M is 16 or less, sufficient strength and flexibility are obtained in the cured product, and excellent adhesive strength and toughness tend to be obtained. From the viewpoint of balancing flexibility, adhesion and toughness of the cured product of the curable composition of this embodiment, 3 ≤ (L + M) ≤ 12 is preferred, 3 ≤ (L + M) ≤ 10 is more preferred, 4 ≤ (L + M) ≤ 8 is even more preferred, and 4 ≤ (L + M) ≤ 7 is even more preferred.

[0049] Furthermore, the composition of this embodiment is a curable composition containing the composition of this embodiment and component D described later, and in terms of the adhesion and toughness of the cured product, G １ A compound of formula (1) in which is a glycidyl group, and G １ It is preferable to include both compounds of formula (1) in which is hydrogen. During the thermosetting reaction, the glycidyl group reacts in a catalytic or addition mode, and the hydrogen group reacts in an addition mode. That is, G １ Compounds of formula (1) in which is a glycidyl group and G １ By including both compounds of formula (1) in which hydrogen is present, it is possible to introduce both a high-strength region with high crosslink density cured by a catalytic method and a flexible region reacted by an addition method into the cured product, thereby obtaining a tough cured product with excellent flexibility and adhesion.

[0050] (Method for producing component A) Examples of methods for producing component A include reacting an oxyalkylene adduct obtained by adding alkylene oxide to a divalent alcohol compound having a six-membered ring structure in a ratio of 2 to 16 molars with an epihalohydrin in the presence of an alkaline compound.

[0051] Examples of epihalohydrins include, but are not limited to, epichlorohydrin and epibromohydrin. The amount of epihalohydrin added is usually 1 to 10 equivalents per equivalent of alcoholic hydroxyl groups of the oxyalkylene adduct.

[0052] Examples of alkaline compounds include, but are not limited to, sodium hydroxide, potassium hydroxide, barium hydroxide, and potassium carbonate. These may be used individually or in combination of two or more. The state of the alkaline compound is not limited to, but may be solid, liquid, or aqueous solution. The amount of alkaline compound added is usually 1 to 10 equivalents per equivalent of alcoholic hydroxyl groups of the oxyalkylene adduct.

[0053] Furthermore, in the method for producing component A, it is preferable to use a phase transfer catalyst from the viewpoint of promoting the reaction. In particular, it is more preferable to use the alkaline compound and the phase transfer catalyst in combination.

[0054] The phase transfer catalyst is not limited to the following, but examples include tetramethylammonium chloride, tetramethylammonium bromide, tetrapropylammonium chloride, tetrapropylammonium bromide, tetrabutylammonium chloride, tetrabutylammonium bromide, tetrabutylammonium iodide, benzyltrimethylammonium chloride, benzyltrimethylammonium bromide, benzyltriethylammonium chloride, benzyltriethylammonium bromide, phenyltrimethylammonium chloride, and other quaternary ammonia. Examples include ammonium salts; quaternary ammonium hydroxides such as tetramethylammonium hydroxide, tetrabutylammonium hydroxide, and benzyltrimethylammonium hydroxide; crown ethers such as 15-crown-5, 18-crown-6, dibenzo-18-crown-6, dicyclohexyl-18-crown-6, and diaza-18-crown-6; and cryptands such as [2.1.1]-cryptand, [2.2.1]-cryptand, [2.2.2]cryptand, [2.2.2]-decylcryptand, and [2.2.2]-benzocryptand. These may be used individually or in combination of two or more. The state of the phase transfer catalyst is not limited to the following, and may be solid, liquid, aqueous solution, alcohol solution, etc.

[0055] The amount of phase transfer catalyst added is typically 0.025 to 10 moles per mole of alcoholic hydroxyl groups of the oxyalkylene adduct.

[0056] The reaction temperature is typically 20 to 100°C, and the reaction time is typically 1 to 12 hours.

[0057] After the reaction is complete, the generated salts, residual alkaline compounds, and phase-transfer catalysts are removed from the reaction solution by washing with water or other means. Then, the residual epihalohydrins are removed by heating under normal or reduced pressure, and the target product, component A, is recovered.

[0058] Furthermore, component A is G in formula (1) above. １ Compounds in which the group is a glycidyl group and G １Methods for synthesizing compounds containing both hydrogen atoms include, but are not limited to, the following: adjusting the amount of epihalohydrin to 2 to 8 equivalents, adjusting the amount of alkaline compound to 2 to 8 equivalents, adjusting the reaction temperature to 30 to 90°C, and adjusting the reaction time to 1.5 to 8 hours.

[0059] (Component B) The composition of this embodiment contains the compound shown in formula (2) as component B.

[0060]

[0061] R ３ R is one selected from the group consisting of an ethylene group, an n-propylene group, an isopropylene group, and an n-butylene group, and when multiple are present, R ３ These may be the same or different. From the viewpoint of the toughness of the cured product of this embodiment, which will be described later, it is more preferable that it be one selected from the group consisting of n-propylene group, isopropylene group, and n-butylene group, and from the viewpoint of excellent low viscosity, it is even more preferable that it be an n-propylene group or isopropylene group.

[0062] In formula (2) above, N is an integer from 1 to 10. From the viewpoint of the flexibility, adhesion, and toughness of the cured product of the curable composition of this embodiment, which will be described later, 2 ≤ N ≤ 9 is preferred, 3 ≤ N ≤ 9 is more preferred, and 4 ≤ N ≤ 8 is even more preferred.

[0063] In the above formula (2), G ２ is a glycidyl group or hydrogen. From the viewpoint of flexibility, adhesion and toughness of the cured product of the curable composition of this embodiment, which will be described later, component B is G ２ Compound (2)-1 in which is hydrogen and G ２ It is preferable that the compound contains both compounds of formula (2)-2, in which the group is a glycidyl group.

[0064]

[0065] In equations (2)-1 and (2)-2, R ３ : One selected from the group consisting of ethylene group, n-propylene group, isopropylene group, and n-butylene group, and R when multiple are present. ３These may be the same or different. Gy: Indicates a glycidyl group. N: An integer from 1 to 10.

[0066] (Method for producing component B) Examples of methods for producing component B include reacting a divalent alcohol compound containing 1 to 10 moles of any of the structures of ethylene oxide, n-propylene oxide, isopropylene oxide, or n-butylene oxide in a linear manner with an epihalohydrin in the presence of an alkaline compound. The epihalohydrin, alkaline compound, phase transfer catalyst, reaction time, reaction temperature, washing method, etc., can be found in the method described above for producing component A: the compound shown in formula (1).

[0067] (Method for producing a composition containing component A: the compound shown in formula (1) and component B: the compound shown in formula (2)) The composition of this embodiment contains component A: the compound shown in formula (1) and component B: the compound shown in formula (2) as described above. The method for producing the composition of this embodiment is not limited to the following, but examples include the following methods (1) to (3). <Method (1)> A method of separately synthesizing component A: the compound shown in formula (1) and component B: the compound shown in formula (2), and then mixing them. <Method (2)> A method to obtain both Component A (compound of formula (1)) and Component B (compound of formula (2)) by first mixing a compound obtained by adding alkylene oxide in a ratio of 2 to 15 molars to a divalent alcohol compound having a six-membered ring structure, which is the raw material for compound (1), and a divalent alcohol compound containing one of the structures of ethylene oxide, n-propylene oxide, isopropylene oxide, or n-butylene oxide in a linear manner in the range of 1 to 10 moles. Then, a glycidylation reaction is carried out to obtain both Component A (compound of formula (1)) and Component B (compound of formula (2)) simultaneously. <Method (3)> A method to obtain both Component A: Compound of Formula (1) and Component B: Compound of Formula (2) simultaneously by performing a glycidylation reaction on a mixture containing a divalent alcohol compound that includes ethylene oxide, n-propylene oxide, isopropylene oxide, or n-butylene oxide in a linear chain in the range of 1 to 10 moles, which is produced by adding alkylene oxide in a ratio of 2 to 15 molars to a divalent alcohol compound having a six-membered ring structure, which is the raw material for compound of Formula (1).

[0068] (Total amount of chlorine contained in the composition) The total amount of chlorine contained in the composition of this embodiment is preferably 2500 ppm or less, more preferably 2000 ppm or less, even more preferably 1500 ppm or less, and even more preferably 900 ppm or less, from the viewpoint of having excellent electrical properties and an excellent balance between curability and storage stability in the curable composition and cured product of this embodiment described later. Furthermore, the total amount of chlorine contained in the composition of this embodiment is preferably 0.01 ppm or more, more preferably 0.05 ppm or more, even more preferably 0.1 ppm or more, and even more preferably 0.5 ppm or more, from the viewpoint of achieving industrial production.

[0069] Here, the total amount of chlorine contained in the composition of this embodiment refers to the total amount of organic and inorganic chlorine, and is a mass-based value relative to the composition of this embodiment. The total amount of chlorine in the composition is measured by the following method. That is, for example, the composition of this embodiment is washed with xylene, and the washing and filtration are repeated until the composition is no longer present in the xylene washing solution. Next, the filtrate is distilled off under reduced pressure at 100°C or below to obtain the composition. 1 to 10 g of the obtained composition sample is accurately weighed to a titration volume of 3 to 7 mL, dissolved in 25 mL of ethylene glycol monobutyl ether, 25 mL of propylene glycol solution with 1 N KOH is added, boiled for 20 minutes, and then the titration volume can be calculated from the titration volume obtained by titration with an aqueous silver nitrate solution.

[0070] Here, of the total chlorine, the chlorine contained in the 1,2-chlorohydrin group is generally called hydrolyzable chlorine. The amount of hydrolyzable chlorine in the composition of this embodiment is preferably 100 ppm or less, more preferably 50 ppm or less, even more preferably 0.01 to 20 ppm or less, and even more preferably 0.05 to 10 ppm or less.

[0071] The hydrolyzable chlorine in the composition of this embodiment is measured by the following method. For example, 3 g of the sample is dissolved in 50 mL of toluene, 20 mL of a methanol solution of 0.1 N KOH is added, the mixture is boiled for 15 minutes, and then the amount obtained by titration with an aqueous silver nitrate solution is calculated.

[0072] (Total content of component A and component B) In the composition of this embodiment, the total content of component A and component B is preferably 5 to 100% by mass, more preferably 30 to 100% by mass, even more preferably 50 to 100% by mass, even more preferably 75 to 100% by mass, even more preferably 90 to 100% by mass, and particularly preferably 100% by mass, from the viewpoint of imparting excellent flexibility, adhesion, and toughness to the cured product of this embodiment described later.

[0073] (Mass ratio of component A to component B) In the composition of this embodiment, the mass ratio of component A to component B is preferably 50:50 to 99:1, more preferably 70:30 to 99:1, even more preferably 80:20 to 98:2, and even more preferably 90:10 to 97:3, from the viewpoint of balancing the flexibility, adhesion, and toughness of the cured product of the curable composition containing the composition of this embodiment.

[0074] (Area on the MS chart of LC-MS) From the viewpoint of balancing the flexibility, adhesion, and toughness of the cured product of the curable composition containing the composition of this embodiment, when the Area area of ​​component A on the MS chart of LC-MS is set to 100, the Area area of ​​component B is preferably 0.5 to 17, more preferably 0.8 to 10, and even more preferably 2.0 to 9.0.

[0075] Methods for controlling the area areas of component A and component B to the above-mentioned numerical ranges include, for example, adjusting the amount of materials added when manufacturing component A and component B, or adjusting the synthesis conditions of the above-mentioned composition. The area areas of component A and component B in the LC-MS chart can be measured by the measurement method described in the examples below.

[0076] From the viewpoint of the flexibility, adhesion, and toughness of the cured product of the curable composition of this embodiment, which will be described later, it is preferable that the composition of this embodiment contains, in the following ratios, component B: the compound of formula (2)-1, in which N=7, and the compound of formula (2)-2, in which N=7. When the area of ​​component A: the compound of formula (1) in the MS chart of LC-MS is set to 100, it is preferable that the area of ​​the compound of formula (2)-1 with N=7 is 0.1 to 2.0 and the area of ​​the compound of formula (2)-2 with N=7 is 0.2 to 3.5. It is even more preferable that the area of ​​the compound of formula (2)-1 with N=7 is 0.2 to 1.5 and the area of ​​the compound of formula (2)-2 with N=7 is 0.4 to 2.5. Furthermore, it is even more preferable that the area of ​​the compound with N=7 in formula (2)-1 is 0.3 to 1.0, and the area of ​​the compound with N=7 in formula (2)-2 is 0.6 to 1.5.

[0077] The method for controlling the compound of formula (2)-1 and the compound of formula (2)-2 with N=7 to the above-mentioned numerical range is not particularly limited, but for example, the following method can be used. That is, using a compound in which one of the structures of ethylene oxide, n-propylene oxide, isopropylene oxide, or n-butylene oxide is polymerized in a linear chain of 7 moles, with hydroxyl groups at both ends, the equivalent amount of epihalohydrin, the equivalent amount of alkaline compound, the reaction temperature, and the reaction time are adjusted so that the MS chart area ratio of the substances of formula (2)-1 and formula (2)-2 becomes a desired ratio. Next, when mixing the compound containing formula (2)-1 and formula (2)-2 with component A shown in formula (1), the addition ratio is adjusted so that the compound area of ​​formula (2)-1 with N=7 and the compound area of ​​formula (2)-2 with N=7, when the Area area of ​​component A shown in formula (1) is set to 100, can be set to a desired value.

[0078] (Component C: Compound of formula (3)) The composition of this embodiment is preferably further comprising Component C: Compound shown in the following formula (3) (hereinafter sometimes referred to as Component C) from the viewpoint of the adhesion of the cured product of the curable composition containing the composition of this embodiment.

[0079]

[0080] The symbols in equation (3) above are as follows: R １ : One selected from the group consisting of ethylene group, n-propylene group, isopropylene group, and n-butylene group, and R when multiple are present. １ They may be the same or different. ２ : Indicates a divalent group having a 6-membered ring structure. L and M: Each is an integer from 1 to 15, independently of the others. L and M: Satisfy 2 ≤ (L + M) ≤ 16.

[0081] In this embodiment, from the viewpoint of the flexibility, adhesion, and toughness of the cured product of the curable composition of this embodiment, which will be described later, component B is G ２ Compound (2)-1 in which is hydrogen and G ２ It is preferable that the compound of formula (2)-2, in which is a glycidyl group, is included, and that component C includes the compound shown in formula (3) from the viewpoint of the adhesion of the cured product of the curable composition of this embodiment, which will be described later.

[0082] When preparing the composition of this embodiment, component C shown in formula (3) may be added after mixing component A shown in formula (1) and component B shown in formula (2), or unreacted raw materials used when synthesizing component A shown in formula (1) may be used.

[0083] The content of component C shown in formula (3) in the composition of this embodiment is preferably 0.0001% by mass or more and less than 30% by mass, more preferably 0.0001% by mass or more and less than 10% by mass, even more preferably 0.0001% by mass or more and less than 2% by mass, and even more preferably 0.0001% by mass or more and less than 1% by mass, from the viewpoint of the adhesion, flexibility, and moisture and heat resistance of the curable composition and cured product containing the composition of this embodiment.

[0084] (Epoxy equivalent of the composition) The epoxy equivalent of the composition of this embodiment is preferably 350 to 400 g / eq., more preferably 360 to 395 g / eq., and even more preferably 365 to 390 g / eq., from the viewpoint of the adhesion and toughness of the composition of this embodiment and the curable composition.

[0085] The epoxy equivalent of the composition of this embodiment can be controlled by adjusting the amounts of component A shown in formula (1), component B shown in formula (2), and other epoxy compounds added. The epoxy equivalents of component A shown in formula (1) and component B shown in formula (2) can be controlled by adjusting the conditions of the manufacturing method described above.

[0086] [Curable Composition] The curable composition of this embodiment contains the composition of this embodiment described above, and a compound that reacts with component A shown in formula (1) and component B shown in formula (2). Component D: The compound that reacts with component A shown in formula (1) and component B shown in formula (2) is not limited to the following, but examples include one or more selected from the group consisting of amine compounds, compounds having a phenol structure, compounds having an acid anhydride structure, compounds having an active ester structure, compounds having a cyanate ester structure, compounds having a thiol group, bismaleimide compounds, benzoxazine compounds, and carbodiimide compounds. The curable composition of this embodiment can be produced by adding component D to the composition of this embodiment described above. With regard to curable compositions, although it is not intended to limit the present invention, specific examples will be shown in the examples described later.

[0087] (Component D) <Amine Compound> The amine compound is not limited to the following, but examples include low molecular weight amine compounds, amine adduct compounds, modified polyamine compounds, aliphatic polyamine compounds, heterocyclic polyamine compounds, alicyclic polyamine compounds, aromatic amine compounds, polyamide amine compounds, ketimine compounds, urethane amine compounds, amide compounds, amine-based latent curing agents, etc. These may be used individually or in combination of two or more.

[0088] Low molecular weight amine compounds include, but are not limited to, methylamine, ethylamine, propylamine, butylamine, ethylenediamine, propylenediamine, hexamethylenediamine, diethylenetriamine, triethylenetetramine, ethanolamine, propanolamine, cyclohexylamine, isophoronediamine, aniline, toluidine, diaminodiphenylmethane, diaminodiphenylsulfone, dimethylamine, diethylamine, dipropylamine, dibutylamine, dipentylamine, dihexylamine, dimethanolamine, diethanolamine, dipropanolamine, dicyclohexylamine Compounds that do not contain tertiary amines such as silamines, piperidines, piperidones, diphenylamines, phenylmethylamines, and phenylethylamines; amino alcohols such as 2-dimethylaminoethanol, 1-methyl-2-dimethylaminoethanol, 1-phenoxymethyl-2-dimethylaminoethanol, 2-diethylaminoethanol, 1-butoxymethyl-2-dimethylaminoethanol, methyldiethanolamine, triethanolamine, and N-β-hydroxyethylmorpholine; aminophenols such as 2-(dimethylaminomethyl)phenol and 2,4,6-tris(dimethylaminomethyl)phenol;Imidazole, 2-methylimidazole, 4-methylimidazole, 2-ethyl-4-methylimidazole, 2-undecylimidazole, 2-heptadecylimidazole, 2-phenylimidazole, 1-aminoethyl-2-methylimidazole, 1-(2-hydroxy-3-phenoxypropyl)-2-methylimidazole, 1-(2-hydroxy-3-phenoxypropyl)-2-ethyl-4-methylimidazole, 1-(2-hydroxy-3- Toxypropyl)-2-methylimidazole, 1-(2-hydroxy-3-butoxypropyl)-2-ethyl-4-methylimidazole, 2-(2-hydroxyphenyl)imidazole, 2-(2-hydroxynaphthalene-1-yl)imidazole, 2-(2-hydroxy-3-methoxyphenyl)imidazole, 2-(3-t-butyl-2-hydroxyphenyl)imidazole, 2-(2-hydroxy-3,5-di-t-butylphenyl)imidazole, 2,4-diamino-6-[2'-methylimidazolyl]ethyl-s-triazine, isocyanuric acid adduct of 2,4-diamino-6-[2'-methylimidazolyl]ethyl-s-triazine, isocyanuric acid adduct of 2-phenylimidazole, 2-phenyl-4,5-dihydroxymethylimidazole, 2-phenyl-4-methyl-5-hydroxymethylimidazole, 2-[[2-(2-hydroxyphenyl)-1H-benzimidazole-1-yl Examples of imidazoles include methylphenol, 2-[[2-(2-hydroxy-3-methoxyphenyl)-1H-benzimidazole-1-yl]methyl]-6-methoxyphenol, 2-[[2-(2-hydroxy-1-naphthalenyl)-1H-benzimidazole-1-yl]methyl]-1-naphthalenol, and 3-[[2-(2,3-dihydroxyphenyl)-1H-benzimidazole-1-yl]methyl]-1,2-benzenediol.

[0089] Furthermore, the low molecular weight amine compounds are not limited to the following, but include, for example, 1-(2-hydroxy-3-phenoxypropyl)-2-phenylimidazoline, 1-(2-hydroxy-3-butoxypropyl)-2-methylimidazoline, 2-methylimidazoline, 2,4-dimethylimidazoline, 2-ethylimidazoline, 2-ethyl-4-methylimidazoline, 2-benzylimidazoline, 2-phenylimidazoline, 2-(o-tolyl)-imidazoline, tetramethylene-bis-imidazoline, 1,1,3-trimethyl- Imidazolins such as 1,4-tetramethylene-bis-imidazoline, 1,3,3-trimethyl-1,4-tetramethylene-bis-imidazoline, 1,1,3-trimethyl-1,4-tetramethylene-bis-4-methylimidazoline, 1,3,3-trimethyl-1,4-tetramethylene-bis-4-methylimidazoline, 1,2-phenylene-bis-imidazoline, 1,3-phenylene-bis-imidazoline, 1,4-phenylene-bis-imidazoline, and 1,4-phenylene-bis-4-methylimidazoline; trimethyl Min, triethylamine, benzyldimethylamine, N,N-dimethyl-ethylamine, N,N-dimethyl-butylamine, N,N-dimethyldecylamine, N,N-dimethyl-m-toluidine, N,N-dimethyl-p-toluidine, 2,6,10-trimethyl-2,6,10-triazaundecane, N,N'-dimethylpiperazine, 1,4-diazabicyclo[2.2.2]octane (DABCO), 1-azabicyclo[2.2.2]octane-3-one, 1,8-diazabicyclo(5,4,0)-undecene-7,1, Tertiary aminoamines such as 5-diazabicyclo(4,3,0)-nonene-5, hexamethylenetetramine, dimethylaminopropylamine, diethylaminopropylamine, dipropylaminopropylamine, dibutylaminopropylamine, dimethylaminoethylamine, diethylaminoethylamine, dipropylaminoethylamine, dibutylaminoethylamine, N-methylpiperazine, N-aminoethylpiperazine, diethylaminoethylpiperazine, 2-dimethylaminopyridine, 4-dimethylaminopyridine, etc.Examples include aminomercaptans such as 2-dimethylaminoethanethiol, 2-mercaptobenzimidazole, 2-mercaptobenzothiazole, 2-mercaptopyridine, and 4-mercaptopyridine; aminocarboxylic acids such as N,N-dimethylaminobenzoic acid, N,N-dimethylglycine, nicotinic acid, isonicotinic acid, and picolinic acid; and aminohydrazides such as N,N-dimethylglycine hydrazide, nicotinic acid hydrazide, and isonicotinic acid hydrazide. These may be used individually or in combination of two or more.

[0090] The amine adduct compounds are not limited to those listed below, but examples include compounds obtained by the reaction of one or more of the following: carboxylic acid compounds, sulfonic acid compounds, urea compounds, isocyanate compounds, and epoxy resins with the low molecular weight amine compounds mentioned above. In this embodiment, the amine adduct compound preferably includes an imidazole-based amine adduct compound. The imidazole-based amine adduct may be a reaction product of imidazoles with one or more of the following: carboxylic acid compounds, sulfonic acid compounds, urea compounds, isocyanate compounds, and epoxy resins. From the viewpoint of the adhesion of the cured product of the curable composition of this embodiment, the imidazole-based amine adduct compound preferably includes a reaction product of imidazoles and epoxy resins, and from the viewpoint of the mechanical strength of the cured product of the curable composition of this embodiment, it is more preferable to include a reaction product of imidazole and bisphenol-type epoxy resins.

[0091] The carboxylic acid compounds that are components of the amine adduct compound are not limited to the following, but examples include succinic acid, adipic acid, sebacic acid, phthalic acid, dimer acid, and the like.

[0092] The sulfonic acid compounds that are components of the amine adduct compound mentioned above are not limited to the following, but examples include ethanesulfonic acid and p-toluenesulfonic acid.

[0093] The urea compound that is a component of the amine adduct compound is not limited to the following, but examples include urea, methylurea, dimethylurea, ethylurea, t-butylurea, and the like.

[0094] The isocyanate compounds that are components of the amine adduct compound mentioned above are not limited to the following, but include, for example, aliphatic diisocyanates, alicyclic diisocyanates, aromatic diisocyanates, aliphatic triisocyanates, and polyisocyanates. The aliphatic diisocyanates are not limited to the following, but include, for example, ethylene diisocyanate, propylene diisocyanate, butylene diisocyanate, hexamethylene diisocyanate, and trimethylhexamethylene diisocyanate. The alicyclic diisocyanates are not limited to the following, but include, for example, isophorone diisocyanate, 4,4'-dicyclohexylmethane diisocyanate, norbornane diisocyanate, 1,4-isocyanatocyclohexane, 1,3-bis(isocyanatomethyl)-cyclohexane, and 1,3-bis(2-isocyanatopropyl-2-yl)-cyclohexane. Aromatic diisocyanates include, but are not limited to, tolylene diisocyanate, 4,4'-diphenylmethane diisocyanate, xylene diisocyanate, and 1,5-naphthalene diisocyanate. Aliphatic triisocyanates include, but are not limited to, 1,6,11-undecane triisocyanate, 1,8-diisocyanate-4-isocyanate methyloctane, and 1,3,6-triisocyanate methylhexane. Polyisocyanates include, but are not limited to, polymethylene polyphenyl polyisocyanate and polyisocyanates derived from the diisocyanate compounds. Polyisocyanates derived from the diisocyanate compounds include isocyanurate-type polyisocyanates, burette-type polyisocyanates, urethane-type polyisocyanates, allohanate-type polyisocyanates, and carbodiimide-type polyisocyanates.

[0095] The epoxy resin that is a component of the amine adduct compound is not limited to the following, but examples include bisphenol A type epoxy resin, bisphenol F type epoxy resin, bisphenol AD ​​type epoxy resin, bisphenol M type epoxy resin, bisphenol P type epoxy resin, tetrabromobisphenol A type epoxy resin, hydrogenated bisphenol A type epoxy resin, biphenyl type epoxy resin, tetramethylbiphenyl type epoxy resin, tetrabromobiphenyl type epoxy resin, diphenyl ether type epoxy resin, benzophenone type epoxy resin, phenylbenzoate type epoxy resin, diphenyl sulfide type epoxy resin, diphenyl sulfoxide type epoxy resin, diphenyl sulfone type epoxy resin, diphenyl disulfide type epoxy resin, naphthalene type epoxy resin, anthracene type epoxy resin, hydroquinone type epoxy resin, methylhydroquinone type epoxy resin, dibutylhydroquinone type epoxy resin, resorcinol type epoxy resin, methylresorcinol type epoxy resin, catechol type epoxy resin Examples include bifunctional epoxy resins such as silicic acid resins; trifunctional epoxy resins such as N,N-diglycidylaminobenzene type epoxy resins and triazine type epoxy resins; tetrafunctional epoxy resins such as tetraglycidyldiaminodiphenylmethane type epoxy resins and diaminobenzene type epoxy resins; polyfunctional epoxy resins such as phenol novolac type epoxy resins, cresol novolac type epoxy resins, triphenylmethane type epoxy resins, tetraphenylethane type epoxy resins, dicyclopentadiene type epoxy resins, naphthol aralkyl type epoxy resins, and brominated phenol novolac type epoxy resins; monoepoxy compounds such as butyl glycidyl ether, hexyl glycidyl ether, phenyl glycidyl ether, allyl glycidyl ether, para-tert-butylphenyl glycidyl ether, ethylene oxide, propylene oxide, paraxylyl glycidyl ether, glycidyl acetate, glycidyl butyrate, glycidyl hexoate, and glycidyl benzoate; and alicyclic epoxy resins. These may be used individually or in combination of two or more types.

[0096] Aromatic amine compounds include, but are not limited to, diaminodiphenylmethane, o-phenylenediamine, m-phenylenediamine, p-phenylenediamine, diaminodiphenylsulfone, diethyltoluenediamine, 1-methyl-3,5-diethyl-2,4-diaminobenzene, 1-methyl-3,5-diethyl-2,6-diaminobenzene, 1,3,5-triethyl-2,6-diaminobenzene, and 3,3'-diethyl-4,4'-diaminodiphenyl Examples include methane, 3,5,3',5'-tetramethyl-4,4'-diaminodiphenylmethane, 4,4'-methylenebis[N-(1-methylpropyl)aniline], trimethylenebis(4-aminobenzoate), polytetramethylene oxide-di-p-aminobenzoate, diaminodiphenyl ether, 1,3-bis(3-aminophenoxy)benzene, dimethylthiotoluenediamine, 1,2-bis(phenylamino)ethane, and aminobenzylamine.

[0097] The amide compound, which is the amine compound of component D, is not limited to the following, but examples include dicyandiamide and its derivatives, guanidine compounds, compounds obtained by adding an acid anhydride to an amine compound, and hydrazide compounds. The hydrazide compounds are not limited to the following, but examples include succinate dihydrazide, adipic acid dihydrazide, phthalate dihydrazide, isophthalate dihydrazide, terephthalate dihydrazide, p-oxybenzoic acid hydrazide, salicylic acid hydrazide, phenylaminopropionic acid hydrazide, maleate dihydrazide, etc. The guanidine compounds are not limited to the following, but examples include dicyandiamide, methylguanidine, ethylguanidine, propylguanidine, butylguanidine, dimethylguanidine, trimethylguanidine, phenylguanidine, diphenylguanidine, toluylguanidine, etc. These may be used individually or in combination of two or more.

[0098] Examples of the amine-based latent curing agent, which is the amine compound of component D, include, but are not limited to, Novacure HX-3721, HX-3722, HX-3613, HX-3921HP, HXA9322HP (manufactured by Asahi Kasei Corporation), Amicure PN-23, PN-23J, PN-40J (manufactured by Ajinomoto Fine Techno Co., Ltd.), and Fujicure FXR-1020, FXR-1030 (manufactured by Fuji Kasei Kogyo Co., Ltd.).

[0099] <Compounds having a phenol structure> Compounds having a phenol structure of component D are not limited to the following, but examples include phenol novolac resin, cresol novolac resin, phenol aralkyl resin, cresol aralkyl resin, naphthol aralkyl resin, biphenyl-modified phenol resin, biphenyl-modified phenol aralkyl resin, dicyclopentadiene-modified phenol resin, aminotriazine-modified phenol resin, naphthol novolac resin, naphthol-phenol cocondensed novolac resin, naphthol-cresol cocondensed novolac resin, allyl acrylphenol resin, etc. These may be used individually or in combination of two or more.

[0100] <Compounds having an acid anhydride structure> Compounds having an acid anhydride structure of component D are not limited to the following, but examples include phthalic anhydride, trimellitic anhydride, pyromellitic anhydride, maleic anhydride, tetrahydrophthalic anhydride, methyltetrahydrophthalic anhydride, methylnadic anhydride, hexahydrophthalic anhydride, methylhexahydrophthalic anhydride, etc. These may be used individually or in combination of two or more.

[0101] <Compounds Having an Active Ester Structure> The compound having an active ester structure of component D is not limited to the following, but active ester compounds disclosed in Japanese Patent Publication No. 2004-277460 and Japanese Patent Publication No. 2013-40270 may be used, and commercially available active ester compounds may also be used. Commercially available active ester compounds are not limited to the following, but examples include DIC Corporation trade names: EXB9451, EXB9460, EXB9460S, HPC-8000-65T (active ester compound containing a dicyclopentadiene-type diphenol structure), EXB9416-70BK (active ester compound containing a naphthalene structure), EXB9050L-62M (active ester compound containing a phosphorus atom), Mitsubishi Chemical Corporation trade names: DC808 (active ester compound containing an acetylated phenol novolac), YLH1026 (active ester compound containing a benzoylated phenol novolac), etc. These may be used individually or in combination of two or more types.

[0102] <Compounds having a cyanate ester structure> Compounds having a cyanate ester structure of component D are not limited to the following, but examples include novolac-type (phenol novolac type, alkylphenol novolac type, etc.) cyanate ester resins, dicyclopentadiene-type cyanate ester resins, bisphenol-type (bisphenol A type, bisphenol F type, bisphenol S type, etc.) cyanate ester resins, and prepolymers in which these are partially triazined. Specific examples of cyanate ester resins include, for example, difunctional cyanate resins such as bisphenol A dicyanate, polyphenol cyanates (oligo(3-methylene-1,5-phenylene cyanate), 4,4'-methylenebis(2,6-dimethylphenyl cyanate), 4,4'-ethylidene diphenyl dicyanate, hexafluorobisphenol A dicyanate, 2,2-bis(4-cyanate)phenylpropane, 1,1-bis(4-cyanatephenylmethane), bis(4-cyanate-3,5-dimethylphenyl)methane, 1,3-bis(4-cyanatephenyl-1-(methylethylidene))benzene, bis(4-cyanatephenyl) thioether, bis(4-cyanatephenyl) ether, polyfunctional cyanate resins derived from phenol novolacs, cresol novolacs, dicyclopentadiene structure-containing phenol resins, and prepolymers in which these cyanate resins are partially triazined. These may be used individually or in combination of two or more types.

[0103] <Compounds containing thiol groups> Compounds containing thiol groups of component D are, for example, any compound containing two or more thiol groups in one molecule, and are not limited to the following, but include, for example, 3,3'-dithiodipropionic acid, trimethylolpropane tris(thioglycolate), pentaerythritol tetrakis(thioglycolate), ethylene glycol dithioglycolate, 1,4-bis(3-mercaptobutyryloxy)butane, tris[(3-mercaptopropionyloxy)-ethyl]-isocyanurate, 1,3,5-tris(3-mercaptobutyloxy) Examples include 1,3,5-triazine-2,4,6(1H,3H,5H)-trione, trimethylolpropanetris(3-mercaptopropionate), pentaerythritol tetrakis(3-mercaptopropionate), pentaerythritol tetrakis(3-mercaptobutyrate), dipentaerythritol hexakis(3-mercaptopropionate), 1,3,4,6-tetrakis(2-mercaptoethyl) glycoluryl, 4-butanedithiol, 1,6-hexanedithiol, and 1,10-decandithiol. From the viewpoint of impact resistance, 1,4-bis(3-mercaptobutyryloxy)butane, 1,3,5-tris(3-mercaptobutyloxyethyl)-1,3,5-triazine-2,4,6(1H,3H,5H)-trione, pentaerythritol tetrakis(3-mercaptopropionate), and pentaerythritol tetrakis(3-mercaptobutyrate) are preferred, and from the viewpoint of low-temperature curability, pentaerythritol tetrakis(3-mercaptopropionate) and pentaerythritol tetrakis(3-mercaptobutyrate) are more preferred. These may be used individually or in combination of two or more.

[0104] <Bismaleimide Compounds> The bismaleimide compound of component D is not limited to the following, but examples include N-alkylbismaleimide compounds and N-phenylbismaleimide compounds.

[0105] <Benzoxazine Compounds> The benzooxazine compound of component D is not limited to the following, but examples include P-d type benzooxazine and F-a type benzooxazine.

[0106] <Carbodiimide Compounds> The carbodiimide compound of component D is not limited to the following, but examples include N,N'-di-o-toluylcarbodiimide, N,N'-diphenylcarbodiimide, N,N'-di-2,6-dimethylphenylcarbodiimide, N,N'-bis(2,6-diisopropylphenyl)carbodiimide, N,N'-bis(propylphenyl)carbodiimide, N,N'-dioctyldecylcarbodiimide, N-triyl-N'-cyclohexylcarbodiimide, N,N'-di-2,2-di-tert-butylphenylcarbodiimide, N-triyl-N Examples include '-phenylcarbodiimide, N,N'-di-p-nitrophenylcarbodiimide, N,N'-di-p-aminophenylcarbodiimide, N,N'-di-p-hydroxyphenylcarbodiimide, N,N'-dicyclohexylcarbodiimide, N,N'-di-p-toluylcarbodiimide, poly(4,4'-dicyclohexylmethanecarbodiimide), poly(N,N'-di-2,6-diisopropylphenylcarbodiimide), poly(1,3,5-triisopropylphenylene-2,4-carbodiimide), and cyclic carbodiimides.

[0107] (Method for producing the curable composition) The method for producing the curable composition of this embodiment includes the step of obtaining a mixture containing at least the composition of this embodiment described above and component D. The steps for obtaining the mixture are not limited to the following, but include the following methods (1) to (3): (1) Adding component D to a composition containing component A and component B of this embodiment. (2) Adding a composition containing component A and component B of this embodiment to component D. (3) Adding component D to a composition containing either component A or component B, and further adding the remaining components of component A or component B. The mixing method included in the method for producing the curable composition of this embodiment is not particularly limited, and examples include thoroughly mixing until uniform using a mixing roll such as a three-roll mixer, a dissolver, a planetary mixer, a kneader, an extruder, etc.

[0108] (Content of components A and B in the curable composition) In the curable composition of this embodiment, the total content of components A and B is preferably 5 to 99.5% by mass, more preferably 10 to 95% by mass, even more preferably 20 to 90% by mass, and even more preferably 30 to 80% by mass, from the viewpoint of imparting excellent flexibility, adhesion, and toughness to the cured product of the curable composition containing the composition of this embodiment.

[0109] (Content of component D in the curable composition) The content of component D in the curable composition can be appropriately changed depending on the reactivity of component D, the reactivity when two or more components D are combined, and the physical properties of the desired cured product. However, from the viewpoint of including sufficient amounts of component A, component B, and other components in order to obtain a cured product, it is preferable that component D is 0.0001 to 90% by mass, more preferably 0.001 to 70% by mass, and even more preferably 0.001 to 50% by mass, relative to the total mass of the curable composition. In particular, when using a compound having an acid anhydride structure, a compound having a phenol structure, a compound having an active ester structure, a compound having a cyanate ester structure, or a compound having a thiol group as component D, it is preferable that the reactive group of component D is 0.3 to 5 equivalents, more preferably 0.5 to 3 equivalents, and even more preferably 0.7 to 1.5 equivalents, relative to 1 equivalent of glycidyl groups of the epoxy compound in the entire curable composition. Furthermore, when an amine compound is used as component D, the amount is preferably 0.0001 to 90% by mass, more preferably 0.001 to 70% by mass, and even more preferably 0.01 to 50% by mass, relative to the total mass of the curable composition. In addition, when an amine compound containing primary and / or secondary amines is used as component D, the content can be adjusted based on the amount of active hydrogen equivalents. In this case, the amount of active hydrogen equivalents is preferably 0.3 to 5 equivalents, more preferably 0.5 to 3 equivalents, and even more preferably 0.7 to 1.5 equivalents, relative to 1 equivalent of glycidyl groups of the epoxy compound in the entire curable composition.

[0110] (Component E: Filler) The curable composition of this embodiment may contain component E: filler. Examples of fillers include organic fillers and inorganic fillers.

[0111] Organic fillers are substances that function as shock absorbers, capable of mitigating stress caused by impact. The curable composition of this embodiment, by containing organic fillers, can further improve adhesion to various connecting members. It also tends to suppress the occurrence and propagation of fillet cracks. Examples of organic fillers, though not limited to the following, include acrylic resins, silicone resins, butadiene rubber, polyesters, polyurethanes, polyvinyl butyral, polyarylate, polymethyl methacrylate, acrylic rubber, polystyrene, NBR, SBR, silicone-modified resins, and organic fine particles of copolymers containing these as components. From the viewpoint of improving adhesion, preferred organic fine particles include, for example, alkyl (meth)acrylate-butadiene-styrene copolymers, alkyl (meth)acrylate-silicone copolymers, silicone-(meth)acrylic copolymers, composites of silicone and (meth)acrylic acid, composites of alkyl (meth)acrylate-butadiene-styrene and silicone, and composites of alkyl (meth)acrylate and silicone. Furthermore, as the organic fine particles, organic fine particles having a core-shell structure and having different compositions in the core layer and shell layer can also be used. Examples of core-shell type organic fine particles include particles in which acrylic resin is grafted onto a silicone-acrylic rubber core, and particles in which acrylic resin is grafted onto an acrylic copolymer. These organic fillers may be used individually or in combination of two or more types.

[0112] Since inorganic fillers can adjust the thermal expansion coefficient of the curable composition of this embodiment, the inclusion of inorganic fillers tends to contribute to improved heat resistance and moisture resistance when the curable composition and cured product of this embodiment are used as underfill material. Examples of inorganic fillers include, but are not limited to, silica, alumina, glass, cordierite, silicone oxide, barium sulfate, barium carbonate, talc, clay, mica powder, zinc oxide, hydrotalcite, boehmite, aluminum hydroxide, magnesium hydroxide, calcium carbonate, magnesium carbonate, magnesium oxide, boron nitride, aluminum nitride, manganese nitride, aluminum borate, strontium carbonate, strontium titanate, calcium titanate, magnesium titanate, bismuth titanate, titanium oxide, zirconium oxide, barium titanate, barium zirconate titanate, barium zirconate, calcium zirconate, zirconium phosphate, and zirconium tungstate phosphate ceramics, carbon nanotubes, graphene and other carbons, metals or alloys such as gold, silver, copper, nickel, aluminum, zinc, tin, lead, solder, indium, and palladium, and particles coated with a thin metal film on a polymer core material. Among these, silica is preferable from the viewpoint of further reducing the warping of the cured product of this embodiment. Examples of silica include amorphous silica, fused silica, crystalline silica, synthetic silica, and hollow silica. From the viewpoint of good packing properties and ease of handling of the composition, a spherical shape is more preferable. Examples of commercially available spherical fused silica include, but are not limited to, the following: Admatex Co., Ltd. trade names: SO-C2, SO-C1, SO-E2, SO-E1, etc.

[0113] Furthermore, when imparting thermal conductivity to the curable composition and cured product of this embodiment, it is preferable to use an inorganic filler that includes, for example, thermally conductive ceramic particles or metal particles. While not limited to the following, it is preferable to include, for example, alumina particles, aluminum nitride particles, boron nitride particles, zinc oxide particles, silicon nitride particles, silicon carbide particles, magnesium oxide particles, gold particles, silver particles, nickel particles, and particles coated with these metal thin films. From the viewpoint of dispersibility, high thermal conductivity, and resistance to oxidative degradation, alumina particles, aluminum nitride particles, boron nitride particles, gold particles, and silver particles are more preferable.

[0114] Furthermore, when imparting magnetism to the curable composition and cured product of this embodiment, it is preferable to use an inorganic filler that contains, for example, magnetic metal oxide powder. Specifically, the magnetic metal oxide powder may be Fe-Mn ferrite powder, Fe-Mn-Mg ferrite powder, Fe-Mn-Mg-Sr ferrite powder, Fe-Mg-Zn ferrite powder, Fe-Mg-Sr ferrite powder, or Fe-Zn-Mn ferrite powder. Examples include ferrite powders such as iron oxide powder (III) and iron oxide powder. Fe-Mn ferrite powder refers to ferrite powder containing Fe and Mn, and Fe-Mn-Zn ferrite powder refers to ferrite powder containing Fe, Mn and Zn. Furthermore, it is also preferable to use an inorganic filler that contains magnetic metal powder. Specifically, examples of the magnetic metal powder include pure iron powder; crystalline or amorphous alloy powders such as Fe-Si alloy powder, Fe-Si-Al alloy powder, Fe-Cr alloy powder, Fe-Cr-Si alloy powder, Fe-Ni-Cr alloy powder, Fe-Cr-Al alloy powder, Fe-Ni alloy powder, Fe-Ni-Si alloy powder, Fe-Ni-B alloy powder, Fe-Ni-Mo alloy powder, Fe-Ni-Mo-Cu alloy powder, Fe-Co alloy powder, Fe-Ni-Co alloy powder, and Co-based amorphous alloy powder. Fe-Cr-Si alloy powder refers to alloy powder containing Fe, Cr, and Si, while Fe-Ni alloy powder refers to alloy powder containing Fe and Ni.

[0115] These inorganic fillers may be used individually or in combination of two or more types.

[0116] When using an organic filler as component E, the content of the organic filler in the curable composition of this embodiment can be appropriately set according to the desired performance and is not limited to the following, but is preferably 1 to 40% by mass, more preferably 2 to 30% by mass, and even more preferably 3 to 15% by mass, relative to the total amount of the curable composition. When the content of the organic filler is 1% by mass or more, stress relaxation occurs, and an effect of improved adhesive strength tends to be obtained. When the content of the organic filler is 40% by mass or less, an effect of heat reflow resistance tends to be obtained.

[0117] Component E: When an inorganic filler is used as the filler, the amount of inorganic filler in the curable composition of this embodiment can be appropriately set according to the desired performance and is not limited to the following, but is preferably 5 to 99% by mass, more preferably 10 to 95% by mass, even more preferably 15 to 90% by mass, even more preferably 20 to 88% by mass, even more preferably 25 to 85% by mass, and particularly preferably 30 to 80% by mass. By setting it within this range, effects such as excellent adhesion, bonding, dimensional stability, and resistance to warping tend to be achieved.

[0118] (Other Additives) The curable composition of this embodiment may, as necessary, further contain epoxy resins other than those described above, such as epoxy resins that do not fall under component A or component B, low molecular weight epoxy compounds, compounds having vinyl groups, compounds having acrylic groups, compounds having methacrylic groups, solvents, silane coupling agents, resins other than epoxy resins, etc. These may be used individually or in combination of two or more.

[0119] <Epoxy resins that do not fall under components A and B> Examples of epoxy resins that do not fall under components A and B include the compounds listed above as raw materials for amine adduct compounds.

[0120] The total chlorine content in the epoxy resin not belonging to component A or component B is preferably 2500 ppm or less, more preferably 2000 ppm or less, even more preferably 1500 ppm or less, and even more preferably 900 ppm or less, from the viewpoint of obtaining a curable composition that has excellent electrical properties and a good balance between curability and storage stability. Furthermore, from the viewpoint of achieving industrial production, it is preferably 0.01 ppm or more, more preferably 0.05 ppm or more, even more preferably 0.1 ppm or more, and even more preferably 0.5 ppm or more.

[0121] The low-molecular-weight epoxy compounds used as other additives are compounds that exclude components A, B, and the compounds exemplified in the epoxy resins described above, and have a viscosity of 1 mPa·s or more and less than 3 Pa·s at 25°C. Low-molecular-weight epoxy compounds are sometimes called reactive diluents.

[0122] Low molecular weight epoxy compounds include, but are not limited to, epoxy compounds without aromatic rings and epoxy compounds having aromatic rings. Examples of monofunctional epoxy compounds without aromatic rings include n-butylglycidyl ether, t-butylglycidyl ether, allylglycidyl ether, and 2-ethylhexylglycidyl ether. Examples of monofunctional epoxy compounds having one or more aromatic rings include styrene oxide, phenylglycidyl ether, cresylglycidyl ether, p-sec-butylphenylglycidyl ether, t-butylphenylglycidyl ether, and compounds such as SY-OPG (product name: Sakamoto Pharmaceutical Co., Ltd.). Examples of bifunctional epoxy compounds that do not have an aromatic ring include 1,4-cyclohexanedimethanol diglycidyl ether, 1,3-cyclohexanedimethanol diglycidyl ether, (3,4-epoxycyclohexyl)methyl-3,4-epoxycyclohexyl carboxylate, ethylene glycol diglycidyl ether, diethylene glycol diglycidyl ether, propylene glycol diglycidyl ether, 1,6-hexanediol diglycidyl ether, neopentyl glycol diglycidyl ether, dicyclopentadiene dimethanol diglycidyl ether, vinylcyclohexene dioxide, Mitsubishi Chemical Corporation product name: YX-8000, and Sakamoto Pharmaceutical Co., Ltd. product name: SR-8EGS. Examples of bifunctional epoxy compounds having one or more aromatic rings include hexahydrophthalate diglycidyl ether, resorcinol diglycidyl ether, tert-butylhydroquinone diglycidyl ether, polyoxyalkylene bisphenol A diglycidyl ether, N,N-diglycidylaniline, and N,N-diglycidyl-o-toluidine. Examples of trifunctional epoxy compounds include trimethylolpropane triglycidyl ether, glycerin triglycidyl ether, and N,N-bis(2,3-epoxypropyl)-4-(2,3-epoxypropoxy)aniline.

[0123] <Compounds containing a vinyl group> Compounds containing a vinyl group are not limited to the following, but examples include styrene, vinylcarbazole, triallyl isocyanurate, allyl glycidyl ether, trimethylolpropanediallyl ether, pentaerythritol triallyl ether, bismaleimide compounds, etc. These may be used individually or in combination of two or more.

[0124] <Compounds containing acrylic groups, compounds containing methacrylic groups> Compounds containing acrylic groups, compounds containing methacrylic groups are not limited to the following, but include, for example, butyl (meth)acrylate, β-carboxyethyl acrylate, isobornyl acrylate, octyl / decyl acrylate, ethoxylated phenyl acrylate, phenol EO modified acrylate, o-phenylphenol EO modified acrylate, paracumylphenol EO modified acrylate, nonylphenol EO modified acrylate, nonylphenol PO modified acrylate, N-acryloyloxyethyl hexahydrogen Talimide, ω-carboxy-polycaprolactone monoacrylate, monohydroxyethyl phthalate acrylate, 2-hydroxy-3-phenoxypropyl acrylate, dipropylene glycol di(meth)acrylate, 1,6-hexanediol di(meth)acrylate, tripropylene glycol di(meth)acrylate, PO-modified neopentyl glycol di(meth)acrylate, tricyclodecane dimethanol di(meth)acrylate, bisphenol FEO-modified di(meth)acrylate, bisphenol AEO-modified di (Meth)acrylate, isocyanuric acid EO modified di(meth)acrylate, polypropylene glycol di(meth)acrylate, polyethylene glycol di(meth)acrylate, neopentyl glycol hydroxypivalate ester di(meth)acrylate, urethane (meth)acrylate, polyester (meth)acrylate, epoxy (meth)acrylate, trimethylolpropane tri(meth)acrylate, trimethylolpropane PO modified tri(meth)acrylate, trimethylolpropane EO modified tri(meth)acrylate Examples include methyl acrylate, isocyanuric acid EO modified (di / tri)(meth)acrylate, pentaerythritol (tri / tetra)(meth)acrylate, glycerin propoxytri(meth)acrylate, pentaerythritol ethoxytetra(meth)acrylate, ditrimethylolpropanetetra(meth)acrylate, dipentaerythritol (penta / hexa)(meth)acrylate, dipentaerythritol hexa(meth)acrylate, diglycerin EO modified (meth)acrylate, polyester (meth)acrylate, etc.These may be used individually or in combination of two or more types.

[0125] Examples of solvents, though not limited to the following, include hydrocarbons such as toluene, xylene, cyclohexane, mineral spirits, and solvent naphtha; ketones such as acetone, methyl ethyl ketone (MEK), methyl isobutyl ketone (MIBK), and cyclohexanone; esters such as ethyl acetate, n-butyl acetate, and propylene glycol monomethyl ethyl ether acetate; alcohols such as isopropanol, n-butanol, butyl cellosolve, butyl carbitol, and 1-methoxy-2-propanol; and amide solvents such as dimethylformamide, dimethylacetamide, and N-methylpyrrolidone.

[0126] A silane coupling agent has at least one hydrolyzable group, such as an alkoxy group or an aryloxy group, bonded to a silicon atom, and may also have an alkyl group, an alkenyl group, or an aryl group bonded to it. Furthermore, the alkyl group may be substituted with an amino group, an alkoxy group, an epoxy group, or a (meth)acryloyloxy group. The silane coupling agent is not limited to the following, but from the viewpoint of improving the uniform dispersion of filler components and improving the adhesion and bonding of the resin composition, it is preferable to include one or more silane coupling agents selected from, for example, aminosilane coupling agents, epoxysilane coupling agents, mercaptosilane coupling agents, styrylsilane coupling agents, acrylatesilane coupling agents, isocyanatesilane coupling agents, sulfidesilane coupling agents, vinylsilane coupling agents, silane coupling agents, organosilazane compounds, and titanate coupling agents.

[0127] Examples of silane coupling agents include aminosilane coupling agents such as 3-aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, 3-aminopropyldiethoxymethylsilane, N-phenyl-3-aminopropyltrimethoxysilane, N-methylaminopropyltrimethoxysilane, N-2(-aminoethyl)-3-aminopropyltrimethoxysilane, N-(2-aminoethyl)-3-aminopropyldimethoxymethylsilane, 3-glycidyloxypropyltrimethoxysilane, and 3-glycidyloxypropyl Epoxysilane coupling agents such as triethoxysilane, 3-glycidyloxypropylmethyldiethoxysilane, 3-glycidyloxypropyl(dimethoxy)methylsilane, glycidylbutyltrimethoxysilane, 2-(3,4-epoxycyclohexyl)ethyltrimethoxysilane, mercaptosilane coupling agents such as 3-mercaptopropyltrimethoxysilane, 3-mercaptopropyltriethoxysilane, 3-mercaptopropylmethyldimethoxysilane, 11-mercaptondecyltrimethoxysilane, p-styryltrimeth Styrylsilane coupling agents such as xysilane, acrylate silane coupling agents such as 3-acrylooxypropyltrimethoxysilane, 3-methacrylooxypropyltrimethoxysilane, 3-methacrylooxypropyldimethoxysilane, 3-methacrylooxypropyltriethoxysilane, 3-methacrylooxypropyldiethoxysilane, isocyanate silane coupling agents such as 3-isocyanatetopropyltrimethoxysilane, bis(triethoxysilylpropyl) disulfide, bis(triethoxysilylpropyl) tetras Sulfidosilane coupling agents such as Rufid, silane coupling agents such as methyltrimethoxysilane, octadecyltrimethoxysilane, phenyltrimethoxysilane, metacloxypropyltrimethoxysilane, imidazolesilane, triazinesilane, t-butyltrimethoxysilane, hexamethyldisilazane, 1,3-divinyl-1,1,3,3-tetramethyldisilazane, hexaphenyldisilazane, trisilazane, cyclotrisilazane, octamethylcyclotetrasilazane, hexabutyldisilazane, hexaoctyldisilazane, 1,Organosilazas such as 3-diethyltetramethyldisilazane, 1,3-di-n-octyltetramethyldisilazane, 1,3-diphenyltetramethyldisilazane, 1,3-dimethyltetraphenyldisilazane, 1,3-diethyltetramethyldisilazane, 1,1,3,3-tetraphenyl-1,3-dimethyldisilazane, 1,3-dipropyltetramethyldisilazane, hexamethylcyclotrisilazane, dimethylaminotrimethylsilazane, and tetramethyldisilazane. Titanium compounds, tetra-n-butyl titanate dimer, titanium-i-propoxyoctylene glycolate, tetra-n-butyl titanate, titanium octylene glycolate, diisopropoxytitanium bis(triethanolamine), dihydroxytitanium bislactate, dihydroxybis(ammonium lactate) titanium, bis(dioctyl pyrophosphate) ethylene titanate, bis(dioctyl pyrophosphate) oxyacetate titanium Isopropyltrioctanoyl titanate, tri-n-butoxytitanium monostearate, tetra-n-butyl titanate, tetra(2-ethylhexyl) titanate, tetraisopropylbis(dioctyl phosphite) titanate, tetraoctylbis(ditridecyl phosphite) titanate, tetra(2,2-diallyloxymethyl-1-butyl)bis(ditridecyl) phosphite titanate, isopropyltrioctanoyl titanate, isopropyltricumylphenyl titanate, isopropyl Examples of titanate-based coupling agents include propyl triisostearoyl titanate, isopropyl isostearoyl diacrylic titanate, isopropyl dimethacrylate isostearoyl titanate, isopropyl tri(dioctyl phosphate) titanate, isopropyl tridodecylbenzenesulfonyl titanate, isopropyl tris(dioctyl pyrophosphate) titanate, and isopropyl tri(N-amidoethyl / aminoethyl) titanate.

[0128] Examples of resins other than epoxy resins include, but are not limited to, silicone resins, phenolic resins, phenoxy resins, polyvinyl butyral resins, polyvinyl acetal resins, polyacrylic resins, polyimide resins, and elastomers having functional groups such as carboxyl groups, hydroxyl groups, vinyl groups, and amino groups.

[0129] [Cured product] The cured product of this embodiment is the cured product of the curable composition of this embodiment described above. The curable composition used for the cured product of this embodiment may contain the composition of this embodiment and component D, as described above, or it may further contain a filler component E.

[0130] [Specific Embodiments of Curable Compositions] The curable composition of this embodiment is suitable for, but is not limited to, underfill materials, encapsulating materials for compression molding, encapsulating materials for electrical and electronic components such as mold underfill materials and relay encapsulating materials, conductive materials such as conductive pastes, thermally conductive materials, insulating materials, adhesives for camera modules, structural adhesives, matrix resins for fiber-reinforced plastics, impregnation and fixing agents for motor coils, etc. In addition to the above, the curable composition of this embodiment is suitable for, but is not limited to, interlayer insulating films, film-type solder resists, encapsulating sheets, conductive films, anisotropic conductive films, thermally conductive films, etc. The curable composition of this embodiment may serve multiple purposes for each of the above-mentioned uses. As an example of this, but is not limited to, when the curable composition of this embodiment contains silver particles as a filler, the conductive material that can be obtained from the curable composition may also be a thermally conductive material. As described above, the curable composition of this embodiment can be preferably applied as a sealing material, a conductive material, a thermally conductive material, an insulating material, an adhesive for camera modules, a structural adhesive, a matrix resin for fiber-reinforced plastics, an impregnating adhesive, an interlayer insulating film, a film-type solder resist, a sealing sheet, a conductive film, an anisotropic conductive film, and / or a thermally conductive film. In other words, the sealing material, conductive material, thermally conductive material, insulating material, an adhesive for camera modules, a structural adhesive, a matrix resin for fiber-reinforced plastics, an impregnating adhesive, an interlayer insulating film, a film-type solder resist, a sealing sheet, a conductive film, an anisotropic conductive film, and a thermally conductive film of this embodiment all include the curable composition of this embodiment and / or the composition of this embodiment.

[0131] The present invention will be described below with reference to specific examples and comparative examples, but the present invention is not limited to the following examples and comparative examples. In the following, "parts" and "%" refer to mass unless otherwise specified.

[0132] [Compositions, Curable Compositions] The components used in the compositions and curable compositions of the examples and comparative examples are listed below.

[0133] (Component A: Synthesis of the compound shown in formula (1)) 100 g of a divalent alcohol compound with an average of 5 moles of isopropylene oxide added per mole of bisphenol A (hydroxyl equivalent: 270 g / eq.), 200 g of epichlorohydrin, and 5 g of a 50% by mass aqueous solution of tetramethylammonium chloride were added to a flask and stirred at 60°C. Next, 150 g of a 48.5% by mass aqueous solution of sodium hydroxide was added dropwise over 2 hours, and the reaction was continued for 5 hours. After cooling the reactants and washing with water to remove sodium chloride, the unreacted epichlorohydrin was removed by vacuum distillation to obtain the compound corresponding to component A (the compound shown in formula (1) above) (epoxy equivalent 375 g / eq.). LC-MS measurement revealed that in formula (1), G １ It was confirmed that the compound contains all compounds in which the glycidyl group is and L+M is between 2 and 10. １ It was confirmed that the compound is hydrogen and contains all compounds where L+M corresponds to 3 to 9. Furthermore, from the LC chart, it was confirmed that the compound containing component C (the compound shown in formula (3) above) is a divalent alcohol compound used as a raw material, which is present at a concentration of 0.8% by mass.

[0134] (Component B: Synthesis of the compound shown in formula (2)) 100 g of polypropylene glycol (hydroxyl equivalent: 225 g / eq.), 210 g of epichlorohydrin, and 5 g of a 50% by mass aqueous solution of tetramethylammonium chloride were added to a flask and stirred at 60°C. Next, 180 g of a 48.5% by mass aqueous solution of sodium hydroxide was added dropwise over 2 hours, and the reaction was continued for 6 hours. After cooling the reactants and washing with water to remove sodium chloride, the unreacted epichlorohydrin was removed by distillation under reduced pressure to obtain the compound corresponding to component B (the compound shown in formula (2) above) (epoxy equivalent 332 g / eq.). LC-MS measurement results showed G ２ It was confirmed that the compound contains all compounds in which the group is a glycidyl group and N is between 3 and 8. ２ We confirmed that it contains all compounds where hydrogen is present and N is between 5 and 9.

[0135] The component B synthesized as described above is separated and purified by silica gel chromatography, thereby obtaining G in formula (2).２ It does not contain compounds in which hydrogen is present, G ２ We obtained component B-P, which contains a compound in which the group is a glycidyl group and has 8 or more nitrogen atoms.

[0136] • YED216D (product name of Mitsubishi Chemical Corporation) (1,6-Hexanediol diglycidyl ether) • jER828 (product name of Mitsubishi Chemical Corporation) (Bisphenol A type epoxy resin, epoxy equivalent 184 g / eq.)

[0137] (Components of the curable composition) ・4,4-diaminodiphenylmethane (manufactured by Wako) ・HN-5500 (product name of Showa Denko Materials) (3 or 4-methyl-hexahydrophthalic anhydride) ・MEH-8000H (product name of Meiwa Kasei Co., Ltd.) (allylated phenol novolac resin, hydroxyl group equivalent 141 g / eq) ・NovaCure HXA9322HP (product name of Asahi Kasei Corporation) (masterbatch type amine-based latent curing agent containing imidazole compounds)

[0138] [Examples 1-5] After weighing the components according to Table 1 below, the components were mixed in a non-bubbling kneader with stirring for 2 minutes and degassing for 3 minutes to obtain the composition. [Examples 6-12, Comparative Examples 1-3] After weighing the components according to Table 2 below, the components were mixed in a non-bubbling kneader with stirring for 2 minutes and degassing for 3 minutes to obtain the curable composition.

[0139] [Evaluation of physical properties of the composition] (Area area of ​​component A and area area of ​​component B in the LC-MS chart of the composition) <LC-MS measurement> Each component was weighed according to Table 1 below, stirred for 2 minutes and degassed for 3 minutes in a non-bubbling kneader, and the mixed composition was measured using LC-MS under the following conditions. The area area values ​​of component B (compound of formula (2)), the compound of formula (2)-1 with N=7, and the compound of formula (2)-2 with N=7 were calculated, with the area area of ​​component A in the LC-MS chart set to 100. <Measurement Conditions> Apparatus: Waters UPLC H-Class (plus) / QDa MS Ionization Auxiliary Solution: 5 mM sodium acetate / methanol solution Column: BEH-C18 1.7 μm Column Temperature: 40°C Sample Concentration: 0.1 wt% (acetonitrile dilution) Injection Volume: 1 μL Flow Rate: 0.2 mL / min Mobile Phase A: Water B: Acetonitrile C: Methanol Gradient A: 56%, B: 30%, C: 14%

[0140] A baseline was drawn on the obtained MS chart and the area was calculated for each peak. Of component B, the compound with N=7 in formula (2)-1 was observed as an independent peak at a retention time of 4.6 minutes, and the compound with N=7 in formula (2)-2 was observed as an independent peak at a retention time of 7.0 minutes. For component A, the total peak area of ​​the compound in formula (1) was calculated and set to 100. Then, the total peak area of ​​the compound in formula (2) for component B, the peak area corresponding to the compound with N=7 in formula (2)-1, and the peak area corresponding to the compound with N=7 in formula (2)-2 were calculated. The calculation results are shown in Table 1 below.

[0141] [Characterization of Curable Compositions] (Measurement of Tensile Elongation of Curable Compositions) Examples 6 to 12 and Comparative Examples 1 to 3 were poured into a Teflon (registered trademark) mold measuring 550 mm in length, 350 mm in width, and 2 mm in thickness, up to the opening. Subsequently, each example and comparative example was heated and cured in an oven under the following conditions to obtain cured pieces: Examples 6, 7, 8, 9, 10, Comparative Examples 1 and 2... 180°C x 2h Examples 11 and 12, Comparative Example 3... 150°C x 1h The obtained cured pieces were cut to 40 mm in length, 5 mm in width, and 2 mm in thickness to obtain cured material samples, which are test pieces for measuring tensile strength. Tensile tests were performed on the obtained test pieces in a constant temperature and humidity chamber at 23°C and 50% RH using an AUTOGRAPH AGS-X5kN (manufactured by Shimadzu) at a unit movement speed of 5 mm / min to obtain the tensile elongation (%). Tensile tests were conducted a total of five times, and the median value of the obtained results was adopted. The following criteria were used to evaluate the tensile elongation: <Evaluation Criteria> 18% or more...◎ 13% to less than 18%...〇 Less than 13%...×

[0142] (Measurement of shear bonding strength of curable compositions on copper plates) Examples 5 to 10 and Comparative Examples 1 to 3 were applied to copper plates (Standard Test Pieces, "C1100P"). Next, glass beads with a particle size of 100 μm were sprinkled on top to adjust the thickness, and then another copper plate was bonded on top so that the bonding area was 12.5 mm × 10.5 mm. Subsequently, each example and comparative example was heated and cured in an oven under the following conditions to obtain test specimens: Examples 6, 7, 8, 9, 10, Comparative Examples 1, 3... 180°C × 2h Examples 11, 12, Comparative Example 2... 150°C × 1h Using the obtained test specimens, the shear bonding strength was measured in a constant temperature and humidity chamber at 23°C and 50% RH using an AUTOGRAPH AGS-X (Shimadzu) at a unit movement speed of 100 mm / min. The median value of the results obtained from n=5 measurements was adopted. The copper plate shear bonding strength was evaluated according to the following criteria: <Evaluation Criteria> 20 MPa or more 15 MPa or more but less than 20 MPa Less than 15 MPa

[0143] (Measurement of fracture toughness (K1c) of curable compositions) Examples 6 to 12 and Comparative Examples 1 to 3 were poured into a Teflon (registered trademark) mold measuring 550 mm in length, 350 mm in width, and 2 mm in thickness, filling it completely to the opening. Subsequently, each example and comparative example was heated and cured in an oven under the following conditions: Examples 6, 7, 8, 9, 10, Comparative Examples 1 and 3... 180°C x 2h Examples 11 and 12, Comparative Example 2... 150°C x 1h The resulting cured material was cut to 40 mm in length, 5 mm in width, and 2 mm in thickness, and a crack was induced in the center using a razor blade to prepare a test specimen. The fracture toughness (K1c) value of the obtained test specimen was obtained in a constant temperature and humidity chamber at 23°C and 50% RH using an AUTOGRAPH AGS-H 5kN (manufactured by Shimadzu Corporation) in the three-point bending mode. The fracture toughness (K1c) value (MPa / m²) is such that the ratio of crack length to width of the specimen is in the range of 0.55 ± 0.1. ０．５ The median value of n=5 measurements was adopted. The following criteria were used to evaluate the K1c value. <Evaluation Criteria> 1.8 MPa / m ０．５ Above...◎ 1.3MPa / m ０．５ 1.8MPa / m or more ０．５ Less than...〇 1.3 MPa / m ０．５ Less than... ×

[0144]

[0145]

[0146] Comparing the curable compositions of Examples 6-12 with those of Comparative Examples 1-3, it was found that Examples 6-10, which included the compositions of Examples 1-5, had a superior balance of properties compared to Comparative Examples 1-3 in terms of tensile strength (representing flexibility), copper plate shear adhesion strength (representing adhesion), and K1c (representing toughness). Comparing Examples 8 and 10, it was found that the inclusion of the compound of formula (2)-1 in component B resulted in superior properties in adhesion and toughness. Furthermore, it was confirmed that Examples 11 and 12, by including the compositions of the present invention, exhibited excellent flexibility, adhesion, and toughness even when various components D were used.

[0147] This application is based on Japanese Patent Application No. 2025-048416, filed with the Japan Patent Office on March 24, 2025, the contents of which are incorporated herein by reference.

[0148] According to the present invention, it is possible to provide a composition and a curable composition that yield a cured product with excellent flexibility, adhesion, and toughness. The composition and curable composition of the present invention have industrial applicability as materials for sealing electrical and electronic components such as underfill materials and relay sealing materials, conductive materials such as conductive pastes, thermally conductive materials, insulating materials, adhesives for camera modules, structural adhesives, matrix resins for fiber-reinforced plastics, impregnation and fixing materials for motor coils, interlayer insulating films, film-type solder resists, sealing sheets, conductive films, anisotropic conductive films, thermally conductive films, and the like.

Claims

1. A composition containing: Component A: A compound shown in the following formula (1), and Component B: A compound shown in the following formula (2). (In equations (1) and (2) above, R １ : One selected from the group consisting of ethylene group, n-propylene group, isopropylene group, and n-butylene group, and R when multiple are present. １ They may be the same or different. ２ : Indicates a divalent group having a six-membered ring structure. R ３ : One selected from the group consisting of ethylene group, n-propylene group, isopropylene group, and n-butylene group, and R when multiple are present. ３ They may be the same or different. Gy: Indicates a glycidyl group. G １ G ２ : Represents a glycidyl group or hydrogen. L and M: Each is an integer from 1 to 15, independently of each other. L and M satisfy 2 ≤ (L + M) ≤ 16. N: An integer from 1 to 10.

2. The composition according to claim 1, wherein the component B comprises a compound represented by the following formula (2)-1 and a compound represented by the following formula (2)-2. (In the above formula (2)-1 and formula (2)-2, R ３ is one selected from the group consisting of an ethylene group, an n-propylene group, an isopropylene group, and an n-butylene group, and when a plurality of R ３ are contained, they may be the same or different from each other. Gy represents a glycidyl group. N is an integer of 1 to 10.) 3. The composition according to claim 1, wherein the mass ratio of component A to component B is such that the mass of component A : the mass of component B = 50:50 to 99:

1.

4. The composition according to claim 1, further comprising: Component C: a compound shown in the following formula (3). (In the above formula (3), R １ : One selected from the group consisting of ethylene group, n-propylene group, isopropylene group, and n-butylene group, and R when multiple are present. １ They may be the same or different. ２ : Indicates a divalent group having a 6-membered ring structure. L and M are independent integers from 1 to 15. L and M satisfy 2 ≤ (L + M) ≤ 16.

5. The composition according to claim 1, wherein, in the MS chart of LC-MS, when the area area of ​​component A is set to 100, the area area of ​​component B is 0.5 to 17.

6. The composition according to claim 2, wherein, in the MS chart of LC-MS, when the area of ​​component A is set to 100, the area of ​​the compound with N=7 in formula (2)-1 is 0.1 to 2.0, and the area of ​​the compound with N=7 in formula (2)-2 is 0.2 to 3.

5.

7. As component A, R in formula (1) １ However, it is an n-propylene group or an isopropylene group, R ２ The compound comprises a compound having the structure of formula (4) or formula (5) below, wherein the component B is R in formula (2). ３ The composition according to claim 1, comprising a compound in which is an n-propylene group or an isopropylene group.

8. As component A, R in formula (1) １ However, it is an n-propylene group or an isopropylene group, R ２ The compound comprises a compound having the structure of formula (4) or formula (5) below, wherein the component B is R in formula (2). ３ The composition according to claim 5, wherein the compound comprises an n-propylene group or an isopropylene group.

9. The aforementioned component B includes the compound shown in formula (2)-1 and the compound shown in formula (2)-2 below. (In equations (2)-1 and (2)-2 above, R ３ : One selected from the group consisting of ethylene group, n-propylene group, isopropylene group, and n-butylene group, and R when multiple are present. ３ The same or different. Gy: indicates a glycidyl group. N: is an integer from 1 to 10.) Furthermore, the composition according to claim 1, comprising: component C: a compound shown in the following formula (3). (In the above formula (3), R １ : One selected from the group consisting of ethylene group, n-propylene group, isopropylene group, and n-butylene group, and R when multiple are present. １ They may be the same or different. ２ : Indicates a divalent group having a 6-membered ring structure. L and M are independent integers from 1 to 15. L and M satisfy 2 ≤ (L + M) ≤ 16.

10. The composition according to claim 9, wherein the content of component C is 0.0001% by mass or more and 2% by mass or less of the total composition.

11. A curable composition comprising the composition according to any one of claims 1 to 10, and component D: a compound that is reactive with the compound of component A shown in formula (1) and the compound of component B shown in formula (2).

12. The curable composition according to claim 11, wherein component D comprises one or more selected from the group consisting of amine compounds, compounds having a phenol structure, compounds having an acid anhydride structure, compounds having an active ester structure, compounds having a cyanate ester structure, compounds having a thiol group, bismaleimide compounds, benzoxazine compounds, and carbodiimide compounds.

13. The curable composition according to claim 12, further comprising component E: filler.

14. A cured product of the curable composition according to claim 12.

15. A cured product of the curable composition according to claim 13.

16. A sealing material comprising the composition according to any one of claims 1 to 10.

17. A conductive material comprising the composition according to any one of claims 1 to 10.

18. A thermally conductive material comprising the composition according to any one of claims 1 to 10.

19. An insulating material comprising the composition according to any one of claims 1 to 10.

20. An adhesive for a camera module comprising the composition according to any one of claims 1 to 10.

21. A structural adhesive comprising the composition according to any one of claims 1 to 10.

22. A matrix resin for fiber-reinforced plastics comprising the composition according to any one of claims 1 to 10.

23. An impregnation adhesive comprising the composition according to any one of claims 1 to 10.

24. An interlayer insulating film comprising the composition according to any one of claims 1 to 10.

25. A film-type solder resist comprising the composition according to any one of claims 1 to 10.

26. A sealing sheet comprising the composition according to any one of claims 1 to 10.

27. A conductive film comprising the composition according to any one of claims 1 to 10.

28. An anisotropic conductive film comprising the composition according to any one of claims 1 to 10.

29. A thermally conductive film comprising the composition according to any one of claims 1 to 10.

Images