Resin composition, cured product, sealing material, adhesive, insulating material, coating material, prepreg, multilayer body, and fiber-reinforced composite material

Abstract

Provided are: a resin composition which maintains excellent heat resistance and has excellent potential; and a cured product, a sealing material, an adhesive, an insulating material, a coating material, a prepreg, a multilayer body, and a fiber-reinforced composite material. A resin composition contains a cyanate ester compound (A), an amine adduct compound (B), and a boric acid ester (C).

Description

Technical Field

[0001] The present invention relates to a resin composition, a cured product, a sealing material, an adhesive, an insulating material, a coating, a prepreg, a multilayer body and a fiber-reinforced composite material, and in particular to a resin composition containing a cyanate ester compound. Background Art

[0002] Cyanate compounds have long been known as thermosetting resins that form triazine rings when cured. The cured product obtained by cyanate has excellent properties such as high glass transition temperature, low dielectric constant and dielectric loss tangent, excellent electrical insulation and flame retardancy. Therefore, cyanate compounds are widely used as raw materials for electrical and electronic materials, structural composite materials, adhesives, and other various functional polymer materials (Patent Document 1, etc.).

[0003] Prior art literature

[0004] Patent Literature

[0005] Patent Document 1: Japanese Patent Application Publication No. 2021-195390 Summary of the invention

[0006] Problem that the invention aims to solve

[0007] As described above, resin compositions containing cyanate compounds have been studied. In recent years, the demand for them has been further expanding. For example, they can also be expected to be used in aerospace materials.

[0008] On the other hand, from the viewpoint of operability and logistics rationalization, it is sought that the resin composition containing the cyanate ester compound can be stored at room temperature, and from the viewpoint of improving productivity, curability, especially curing at a temperature below a specified temperature, is desired. In particular, for resin compositions for prepregs, potential (for example, stability of resin compositions below about 80°C and curability of resin compositions between about 100 and 185°C) is sought. In addition, it is also sought that the resin composition containing the cyanate ester compound does not adversely affect the original heat resistance.

[0009] An object of the present invention is to solve the above-mentioned problems, and an object of the present invention is to provide a resin composition having excellent potential while maintaining excellent heat resistance, and a cured product, a sealing material, an adhesive, an insulating material, a coating material, a prepreg, a multilayer body, and a fiber-reinforced composite material.

[0010] Solutions for solving problems

[0011] The present inventors have conducted studies based on the above problems and have found that the above problems can be solved by blending an amine adduct compound and a boric acid ester with a cyanate ester compound.

[0012] Specifically, the above-mentioned problems are solved by the following means.

[0013] <1> A resin composition comprises a cyanate compound (A), an amine adduct compound (B) and a borate ester (C).

[0014] <2> according to <1> The resin composition, wherein the cyanate ester compound (A) comprises at least one selected from the group consisting of compounds represented by the following formula (I) and compounds represented by the following formula (II).

[0015]

[0016] (In formula (I), Ar1 each independently represents an aromatic ring; Ra each independently represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, an aryl group having 6 to 12 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms, and the alkyl group or aryl group in Ra may have a substituent; a represents the number of bonds of cyano groups bonded to Ar1, and each independently represents an integer of 1 to 3; b represents the number of bonds of Ra bonded to Ar1, and each independently represents the number obtained by subtracting (a+2) from the number of substitutable groups of Ar1; c is an integer of 1 to 50; X each independently represents a single bond, a divalent organic group having 1 to 50 carbon atoms, a sulfonyl group (-SO2-), a divalent sulfur atom (-S-), or a divalent oxygen atom (-O-).)

[0017]

[0018] (In formula (II), Ar2 represents an aromatic ring; Rb each independently represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 12 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms, and the alkyl group or aryl group in Rb may optionally have a substituent; d represents the number of cyano groups bonded to Ar2, which is an integer of 2 to 3; e represents the number of Rb groups bonded to Ar2, which is the number obtained by subtracting (d+2) from the number of substitutable groups of Ar2.)

[0019] <3> according to <2> The resin composition, wherein X in the above formula (I) each independently represents a divalent linking group selected from the group consisting of the following formulae (III) to (XIV).

[0020]

[0021] (In formula (III), Ar3 each independently represents an aromatic ring; Rc, Rd, Rg and Rh each independently represent a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or an aryl group having 6 to 12 carbon atoms, and the alkyl group or aryl group in Rc, Rd, Rg and Rh may have a substituent; Re and Rf each independently represent a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 12 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms, and the alkyl group or aryl group in Re and Rf may have a substituent; f represents an integer of 0 to 5.)

[0022]

[0023] (In formula (IV), Ar4 each independently represents an aromatic ring; Ri and Rj each independently represent a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 12 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms, and the alkyl group or aryl group in Ri and Rj may optionally have a substituent; g represents an integer of 0 to 5.)

[0024]

[0025] (In formula (VIII), h represents an integer of 4 to 7; in formula (XIII), Rk each independently represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.)

[0026] <4> according to <1> ~ <3> The resin composition described in any one of the preceding claims, wherein the cyanate ester compound (A) comprises at least one selected from the group consisting of a compound represented by the following formula (XV) and a compound represented by the following formula (XVI).

[0027]

[0028] (In formula (XV), Ar5 each independently represents an aromatic ring; R1 each independently represents a methylene group, a methyleneoxy group, a methyleneoxymethylene group or an oxymethylene group, and a group obtained by linking two or more of these groups; Rm and Rn each independently represent a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 12 carbon atoms or an alkoxy group having 1 to 4 carbon atoms, and the alkyl group or aryl group in Rm and Rn may optionally have a substituent; i represents the number of cyano groups bonded to Ar5, which is an integer of 1 to 3; j represents the number of Rm bonds to Ar5, which is a number obtained by subtracting (i+2) from the number of substitutable groups of Ar5; k represents the number of Rn bonds to Ar5, which is a number obtained by subtracting 2 from the number of substitutable groups of Ar5; l represents an integer greater than 1; m represents an integer greater than 1; the arrangement of each repeating unit is arbitrary.)

[0029]

[0030] (In formula (XVI), Ar6 each independently represents an aromatic ring; Ro each independently represents a methylene group, a methyleneoxy group, a methyleneoxymethylene group or an oxymethylene group, or a group obtained by linking them; Rp and Rq each independently represent a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 12 carbon atoms or an alkoxy group having 1 to 4 carbon atoms, and the alkyl group or aryl group in Rp and Rq may optionally have a substituent; n represents the number of bonds of cyano groups bonded to Ar6, which is an integer of 2 to 3; o represents the number of bonds of Rp bonded to Ar6, which is a number obtained by subtracting (n+2) from the number of substitutable groups of Ar6; p represents the number of bonds of Rq bonded to Ar6, which is a number obtained by subtracting 2 from the number of substitutable groups of Ar6. q represents an integer greater than 1.)

[0031] <5> according to <1> ~ <4> The resin composition described in any one of the preceding claims, wherein the content of the amine adduct compound (B) is 0.01 to 30 parts by mass based on 100 parts by mass of the cyanate ester compound (A).

[0032] <6> according to <1> ~ <5> The resin composition described in any one of the preceding claims, wherein the content of the boric acid ester (C) is 0.01 to 15 parts by mass based on 100 parts by mass of the cyanate ester compound (A).

[0033] <7> according to <1> ~ <6> The resin composition described above further comprises a phenol compound (D).

[0034] <8> according to <7> The resin composition described above, wherein the content of the phenol compound (D) is 1 to 20 parts by mass based on 100 parts by mass of the cyanate compound (A).

[0035] <9> according to <1> ~ <8> The resin composition described above further comprises a toughness imparting agent (E).

[0036] <10> according to <9> In the resin composition, the toughening agent (E) comprises a thermoplastic resin.

[0037] <11> according to <9> or <10> In the resin composition, the toughening agent (E) comprises a powdered resin.

[0038] <12> according to <9> ~ <11> The resin composition described in any one of the preceding claims, wherein the content of the toughening agent (E) is 1 to 40 parts by mass based on 100 parts by mass of the cyanate ester compound (A).

[0039] <13> according to <1> ~ <11> The resin composition according to any one of the preceding claims, wherein the content of the amine adduct compound (B) is 0.01 to 30 parts by mass relative to 100 parts by mass of the cyanate compound (A),

[0040] The content of the boric acid ester (C) is 0.01 to 15 parts by mass based on 100 parts by mass of the cyanate ester compound (A).

[0041] The resin composition further comprises a phenol compound (D),

[0042] The content of the phenol compound (D) is 1 to 20 parts by mass based on 100 parts by mass of the cyanate compound (A).

[0043] <14> according to <13> The resin composition further comprises a toughening agent (E), wherein the content of the toughening agent (E) is 1 to 40 parts by mass relative to 100 parts by mass of the cyanate compound (A).

[0044] <15> A solidified material, which is <1> ~ <14> A cured product of any one of the resin compositions.

[0045] <16> A sealing material comprising <1> ~ <14> The resin composition described above.

[0046] <17> An adhesive comprising <1> ~ <14> The resin composition described above.

[0047] <18> An insulating material comprising <1> ~ <14> The resin composition described above.

[0048] <19> A coating comprising <1> ~ <14> The resin composition described above.

[0049] <20> A prepreg comprising a base material and <1> ~ <14> The resin composition described in any one of the above is formed.

[0050] <21> A multilayer body comprising <20> The prepreg is formed.

[0051] <22> A fiber-reinforced composite material comprising reinforcing fibers and <1> ~ <14> A cured product of any one of the resin compositions.

[0052] Effects of the Invention

[0053] According to the present invention, a resin composition having excellent potential while maintaining excellent heat resistance, and a cured product, a sealing material, an adhesive, an insulating material, a coating material, a prepreg, a multilayer body, and a fiber-reinforced composite material can be provided. DETAILED DESCRIPTION

[0054] Hereinafter, a mode for carrying out the present invention (hereinafter referred to as "this embodiment") will be described in detail. It should be noted that the following this embodiment is an example for explaining the present invention, and the present invention is not limited to this embodiment.

[0055] In addition, in this specification, "to" is used to mean that the numerical values ​​described before and after it are included as a lower limit and an upper limit.

[0056] In this specification, various physical property values ​​and characteristic values ​​are values ​​at 23° C. unless otherwise specified.

[0057] When the measurement methods and the like described in the standards shown in this manual vary from year to year, unless otherwise noted, they are based on the standards as of January 1, 2022.

[0058] In this specification, the resin solid content refers to the components other than the filler and the solvent, and includes the cyanate compound (A), the amine adduct compound (B) and the borate ester (C), as well as other thermosetting compounds and other resin additive components (phenol compound (D), toughening agent (E), etc.) blended as needed.

[0059] The resin composition of the present embodiment is characterized in that it contains a cyanate compound (A), an amine adduct compound (B) and a borate ester (C). By adopting such a configuration, a resin composition having excellent potential while maintaining excellent heat resistance can be obtained.

[0060] The mechanism is speculated as follows. That is, it can be speculated that in the resin composition of the present embodiment, for the cyanate compound (A), the nitrogen atom part of the amine adduct compound (B) acts as a catalyst during the curing of the cyanate compound (A). On the other hand, it can be speculated that when the resin composition is stored, the boron of the borate (C) will shield the nitrogen atom of the amine adduct compound (B), inhibit the curing of the resin composition, and ensure the stability of the resin composition. That is, it can be speculated that the situation in which the amine adduct compound (B) acts as a catalyst during the curing of the cyanate compound (A) during storage is suppressed. In addition, it can be speculated that the bond between the boron of the borate (C) and the nitrogen atom of the amine adduct compound (B) is broken by heating. That is, by heating, the amine adduct compound (B) acts as a catalyst to promote the curing of the cyanate compound (A). Furthermore, it can be speculated that the borate (C) as a Lewis acid also acts as a catalyst during the curing of the cyanate compound (A). Furthermore, the inventors have found that the resin composition of the present embodiment can maintain heat resistance at a high level even when an amine adduct compound (B) and a boric acid ester (C) are blended, thereby completing the present invention.

[0061] <Cyanate Compound (A)>

[0062] The resin composition of the present embodiment contains a cyanate compound (A).

[0063] The cyanate compound (A) is preferably a compound having two or more -OCN groups in one molecule, and more preferably a compound having 2 to 10 -OCN groups in one molecule. The cyanate compound (A) of the present embodiment may be a prepolymer of a cyanate compound.

[0064] More specifically, as the cyanate compound (A), reference can be made to the cyanate ester resins described in paragraphs 0027 to 0028 of JP-A-2022-046517, paragraphs 0024 to 0043 of JP-A-2022-046517, and paragraphs 0012 to 0014 of JP-A-2020-012065, the contents of which are incorporated herein by reference.

[0065] In the present embodiment, the cyanate compound (A) preferably contains at least one selected from the group consisting of a compound represented by the following formula (I) and a compound represented by the following formula (II).

[0066]

[0067] (In formula (I), Ar1 each independently represents an aromatic ring; Ra each independently represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, an aryl group having 6 to 12 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms, and the alkyl group or aryl group in Ra may have a substituent; a represents the number of bonds of cyano groups bonded to Ar1, and each independently represents an integer of 1 to 3; b represents the number of bonds of Ra bonded to Ar1, and each independently represents the number obtained by subtracting (a+2) from the number of substitutable groups of Ar1; c is an integer of 1 to 50; X each independently represents a single bond, a divalent organic group having 1 to 50 carbon atoms, a sulfonyl group (-SO2-), a divalent sulfur atom (-S-), or a divalent oxygen atom (-O-).)

[0068]

[0069] (In formula (II), Ar2 represents an aromatic ring; Rb each independently represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 12 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms, and the alkyl group or aryl group in Rb may optionally have a substituent; d represents the number of cyano groups bonded to Ar2, which is an integer of 2 to 3; e represents the number of Rb groups bonded to Ar2, which is the number obtained by subtracting (d+2) from the number of substitutable groups of Ar2.)

[0070] In formula (I), Ar1 each independently represents an aromatic ring. The aromatic ring represented by Ar1 is not particularly limited, and examples thereof include phenyl and naphthyl.

[0071] In formula (I), Ra each independently represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, an aryl group having 6 to 12 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms, and is preferably a hydrogen atom or an alkenyl group having 2 to 6 carbon atoms. The alkyl group or aryl group in Ra may have a substituent.

[0072] The alkyl group having 1 to 6 carbon atoms is not particularly limited, and examples thereof include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, neopentyl, n-hexyl, cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl. The alkyl group may be linear, branched, or cyclic.

[0073] The alkenyl group having 2 to 6 carbon atoms is not particularly limited, and examples thereof include vinyl, allyl, butenyl, pentenyl, and hexenyl. Among them, an alkenyl group having 2 to 10 carbon atoms is preferred, and an alkenyl group having 2 to 5 carbon atoms is more preferred. In addition, the alkenyl group may be any of linear, branched, and cyclic.

[0074] The alkoxy group having 1 to 4 carbon atoms is not particularly limited, and examples thereof include methoxy, ethoxy, propoxy, butoxy, etc. The alkoxy group may be linear, branched, or cyclic.

[0075] The aryl group having 6 to 12 carbon atoms is not particularly limited, and examples thereof include phenyl and naphthyl.

[0076] The substituent which the alkyl group or aryl group in Ra may have is not particularly limited, and examples thereof include a halogen atom, an alkyl group, a cyano group, an alkoxy group, a carbonyl group, an amino group, an imino group, a thiol group, a sulfone group, a nitro group, an acyl group, an aldehyde group, and an aryl group.

[0077] In formula (I), a represents the number of cyano groups bonded to Ar1, and each a is independently an integer of 1 to 3, preferably an integer of 1 to 2, and more preferably 1.

[0078] In formula (I), b represents the number of bonds of Ra bonded to Ar1, and each independently represents the number obtained by subtracting (a+2) from the number of substitutable groups of Ar1.

[0079] In formula (I), c is an integer of 1 to 50, preferably an integer of 1 to 10, more preferably an integer of 1 to 5, and further preferably 1.

[0080] In formula (I), X each independently represents a single bond, a divalent organic group having 1 to 50 carbon atoms, a sulfonyl group (-SO2-), a divalent sulfur atom (-S-), or a divalent oxygen atom (-O-). The divalent organic group having 1 to 50 carbon atoms represented by X is not particularly limited, and preferably includes, for example, a divalent organic group having 1 to 10 nitrogen atoms (-NRN- (where R represents an organic group)), a carbonyl group (-CO-), a carboxyl group (-C(=O)O-), a carbonyl dioxide group (-OC(=O)O-), and a divalent linking group selected from the group consisting of structures represented by formulas (III) to (XIV) described later, and more preferably represents a divalent linking group selected from the group consisting of formulas (III) to (XIV).

[0081]

[0082] (In formula (III), Ar3 each independently represents an aromatic ring; Rc, Rd, Rg and Rh each independently represent a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or an aryl group having 6 to 12 carbon atoms, and the alkyl group or aryl group in Rc, Rd, Rg and Rh may have a substituent; Re and Rf each independently represent a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 12 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms, and the alkyl group or aryl group in Re and Rf may have a substituent; f represents an integer of 0 to 5.)

[0083]

[0084] (In formula (IV), Ar4 each independently represents an aromatic ring; Ri and Rj each independently represent a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 12 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms, and the alkyl group or aryl group in Ri and Rj may optionally have a substituent; g represents an integer of 0 to 5.)

[0085]

[0086] (In formula (VIII), h represents an integer of 4 to 7; in formula (XIII), Rk each independently represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.)

[0087] In formula (III) and formula (IV), as the aromatic ring represented by Ar3 and Ar4, the same aromatic ring as the aromatic ring represented by Ar1 can be exemplified, and the preferred range is also the same. In addition, in the above formula, as the alkyl group having 1 to 6 carbon atoms, the aryl group having 6 to 12 carbon atoms, the alkoxy group having 1 to 4 carbon atoms and the substituents thereof represented by Rc, Rd, Rg, Rh, Re, Rf, Ri and Rj, the same groups as the groups represented by Ra can be exemplified, and the preferred range is also the same.

[0088] In the formula (II), Ar2 represents an aromatic ring, and has the same meaning as Ar1 in the formula (I), and the preferred range is also the same.

[0089] In formula (II), Rb each independently represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 12 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms. The alkyl group or aryl group in Rb may optionally have a substituent and has the same meaning as Ra in formula (I) and the same preferred range.

[0090] In formula (II), d represents the number of cyano groups bonded to Ar2, which is an integer of 2 to 3; e represents the number of Rb groups bonded to Ar2, which is the number obtained by subtracting (d+2) from the number of substitutable groups of Ar2.

[0091] Furthermore, the cyanate compound (A) more preferably contains at least one selected from the group consisting of a compound represented by the following formula (XV) and a compound represented by the following formula (XVI).

[0092]

[0093] (In formula (XV), Ar5 each independently represents an aromatic ring; R1 each independently represents a methylene group, a methyleneoxy group, a methyleneoxymethylene group or an oxymethylene group, and a group obtained by linking two or more of these groups; Rm and Rn each independently represent a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 12 carbon atoms or an alkoxy group having 1 to 4 carbon atoms, and the alkyl group or aryl group in Rm and Rn may optionally have a substituent; i represents the number of cyano groups bonded to Ar5, which is an integer of 1 to 3; j represents the number of Rm bonds to Ar5, which is a number obtained by subtracting (i+2) from the number of substitutable groups of Ar5; k represents the number of Rn bonds to Ar5, which is a number obtained by subtracting 2 from the number of substitutable groups of Ar5; l represents an integer greater than 1; m represents an integer greater than 1; the arrangement of each repeating unit is arbitrary.)

[0094] In the formula (XV), examples of the aromatic ring represented by Ar5 include the same aromatic rings as those exemplified for Ar1, and the preferred range is also the same.

[0095] In formula (XV), examples of the alkyl group having 1 to 6 carbon atoms, the aryl group having 6 to 12 carbon atoms, the alkoxy group having 1 to 4 carbon atoms, and substituents thereof represented by Rm and Rn include the same groups as exemplified in Ra, and the preferred ranges are also the same.

[0096] In the formula (XV), l represents an integer of 1 or more, preferably 1-10, and more preferably 1-5.

[0097] In the formula (XV), m represents an integer of 1 or more, preferably 1-10, more preferably 1-5.

[0098]

[0099] (In formula (XVI), Ar6 each independently represents an aromatic ring; Ro each independently represents a methylene group, a methyleneoxy group, a methyleneoxymethylene group or an oxymethylene group, or a group obtained by linking them; Rp and Rq each independently represent a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 12 carbon atoms or an alkoxy group having 1 to 4 carbon atoms, and the alkyl group or aryl group in Rp and Rq may optionally have a substituent; n represents the number of bonds of cyano groups bonded to Ar6, which is an integer of 2 to 3; o represents the number of bonds of Rp bonded to Ar6, which is a number obtained by subtracting (n+2) from the number of substitutable groups of Ar6; p represents the number of bonds of Rq bonded to Ar6, which is a number obtained by subtracting 2 from the number of substitutable groups of Ar6. q represents an integer greater than 1.)

[0100] In the formula (XVI), examples of the aromatic ring represented by Ar6 include the same aromatic rings as those exemplified for Ar1, and the preferred range is also the same.

[0101] In formula (XVI), examples of the alkyl group having 1 to 6 carbon atoms, the aryl group having 6 to 12 carbon atoms, the alkoxy group having 1 to 4 carbon atoms, and substituents thereof represented by Rp and Rq include the same groups as exemplified for Ra, and the preferred ranges are also the same.

[0102] In the formula (XVI), q represents an integer of 1 or more, preferably 1-10, and more preferably 1-5.

[0103] As described above, the cyanate compound (A) used in the present embodiment may be a prepolymer. Examples of prepolymers may include prepolymers (remaining with a portion of cyanate groups) of reactants of more than 2 molecules (preferably 2 to 10 molecules) of the compound represented by the above formula (I) and / or the compound represented by the above formula (II). By using such a prepolymer, it is easy to prepare a resin composition with excellent operability when preparing a prepreg.

[0104] The content of the cyanate compound (A) in the resin combination of the present embodiment is preferably more than 50 mass parts relative to 100 mass parts of the resin solids contained in the resin combination, more preferably more than 60 mass parts, more preferably more than 65 mass parts, more preferably more than 70 mass parts, and more preferably more than 75 mass parts. By being set to more than the aforementioned lower limit, there is a tendency that high heat resistance further improves. In addition, the upper limit of the content of the aforementioned cyanate compound (A) is that the resin solids of the amine adduct compound (B) and the boric acid ester (C) all become the amount of the cyanate compound (A), specifically, relative to 100 mass parts of the resin solids contained in the resin combination, preferably less than 99 mass parts, more preferably less than 97 mass parts.

[0105] The resin composition of the present embodiment may contain only one cyanate compound (A) or two or more cyanate compounds (A). When two or more cyanate compounds (A) are contained, the total amount is preferably within the above range.

[0106] <Amine adduct compound (B)>

[0107] The resin composition of the present embodiment contains an amine adduct compound (B). By containing the amine adduct compound (B), a resin composition having excellent stability during storage and excellent curability during heating can be obtained.

[0108] The amine adduct compound (B) is usually solid at room temperature (e.g., 25°C), and begins to soften by heating, and the reactivity is improved. The softening temperature of the amine adduct compound (B) is preferably 90°C or more, more preferably 100°C or more, and preferably 150°C or less, more preferably 145°C or less. By setting it to be above the above lower limit, there is a tendency for the stability during storage to be further improved. In addition, by setting it to be below the above upper limit, there is a tendency for the curing property to be further improved. The above softening temperature is obtained by the test method based on JIS K7234:1986.

[0109] The amine adduct compound (B) is an adduct of an amine compound, preferably an adduct of an amine compound (preferably an imidazole compound or a compound having a tertiary amino group) and at least one compound selected from the group consisting of a carboxylic acid compound, a sulfonic acid compound, a urea compound, an isocyanate compound and an epoxy resin, more preferably an adduct of an amine compound and at least one compound selected from the group consisting of a urea compound, an isocyanate compound and an epoxy resin, and further preferably an adduct of an amine compound with an isocyanate compound and / or an epoxy resin.

[0110] The amine may have one or more active hydrogen in one molecule and one or more (preferably 1 to 3, more preferably 1 or 2, and even more preferably 1) selected from the group consisting of primary amino groups, secondary amino groups, and tertiary amino groups in one molecule, preferably one or more secondary amino groups or tertiary amino groups in one molecule. As the amine compound, as described above, an imidazole compound or a compound having a tertiary amino group is preferred.

[0111] Examples of the imidazole compound include 2-ethyl-4-methylimidazole, 2-methylimidazole, 2-ethyl-4-methylimidazoline, 2,4-dimethylimidazoline, 1-(2-hydroxy-3-phenoxypropyl)-2-methylimidazole, 1-(2-hydroxy-3-phenoxypropyl)-2-ethyl-4-methylimidazole, 1-(2-hydroxy-3-butoxypropyl)-2-methylimidazole, 1-(2-hydroxy-3-butoxypropyl)-2-ethyl-4-methylimidazole, 1-(2-hydroxy-3-phenoxypropyl)-2-phenylimidazoline, and 1-(2-hydroxy-3-butoxypropyl)-2-methylimidazoline.

[0112] Examples of the compound having a tertiary amino group include dimethylaminopropylamine, diethylaminopropylamine, di-n-propylaminopropylamine, dibutylaminopropylamine, dimethylaminoethylamine, diethylaminoethylamine, N-methylpiperazine, N-aminoethylpiperazine, 1,4-bis(3-aminopropyl)piperazine, 2-dimethylaminoethanol, 1-methyl-2-dimethylaminoethanol, 1-phenoxymethyl-2-dimethylaminoethanol, 2-diethylaminoethanol, 1-butoxymethyl-2-dimethylaminoethanol, dimethylaminomethylphenol, 2,4,6-tri(dimethylamino)ethanol, 4-(2-(4-(2-(2-(4-(2-(2-(4-nitrophenyl)amino)phenyl)phenol, N-β-hydroxyethylmorpholine, 2-dimethylaminoethanethiol, 1,4-diazabicyclo[2.2.2]octane, N,N-dimethyl-N'-phenylurea, N,N-dimethyl-N'-(3,4-dichlorophenyl)urea, toluenebis(dimethylurea), 4,4'-methylenebis(phenyldimethylurea), 2-mercaptopyridine, N,N-dimethylaminobenzoic acid, N,N-dimethylglycine, nicotinic acid, isonicotinic acid, picolinic acid, N,N-dimethylglycine hydrazide, N,N-dimethylpropionic acid hydrazide, nicotinic acid hydrazide, isonicotinic acid hydrazide.

[0113] The urea compound is not particularly limited as long as it is a compound having at least one selected from the group consisting of a urea bond, a urea bond, and NH—CO—N, and examples thereof include urea, urea phosphate, urea oxalate, urea acetate, diacetyl urea, dibenzoyl urea, and trimethyl urea.

[0114] The isocyanate compound is not particularly limited. Examples thereof include monofunctional isocyanate compounds such as n-butyl isocyanate, phenyl isocyanate, and hexamethylene diisocyanate; and polyfunctional compounds such as hexamethylene diisocyanate, toluene diisocyanate, 1,5-naphthalene diisocyanate, isophorone diisocyanate, xylylene diisocyanate, and 1,3,6-hexamethylene triisocyanate.

[0115] The epoxy resin is not particularly limited. Examples thereof include polyphenols such as bisphenol A, bisphenol F, bisphenol AD, catechol, and resorcinol; polyglycidyl ethers obtained by reacting polyols such as glycerol and polyethylene glycol with epichlorohydrin; glycidyl ether esters obtained by reacting hydroxycarboxylic acids such as p-hydroxybenzoic acid and β-hydroxynaphthoic acid with epichlorohydrin; polyglycidyl esters obtained by reacting polycarboxylic acids such as phthalic acid and terephthalic acid with epichlorohydrin; epoxidized phenol novolac resins, epoxidized cresol novolac resins, epoxidized polyolefins, cycloaliphatic epoxy resins, urethane-modified epoxy resins, and glycidylamine-type epoxy resins obtained from 4,4-diaminodiphenylmethane, m-aminophenol, and the like.

[0116] The amine adduct compound (B) used in the present embodiment may be any of the materials described in paragraphs 0067 to 0077 of Japanese Patent Application Publication No. 2021-075698, paragraphs 0040 to 0052 of Japanese Patent Application Publication No. 2019-123825, paragraphs 0030 to 0038 of Japanese Patent Application Publication No. 2016-153513, paragraph 0023 of Japanese Patent Application Publication No. 2013-151700, paragraphs 0037 to 0051 of Japanese Patent Application Publication No. 2020-200389, and paragraphs 0026 to 0036 of Japanese Patent Application Publication No. 2020-100684, in addition to the above, and these contents are incorporated herein by reference.

[0117] The content of the amine adduct compound (B) in the resin composition of the present embodiment is preferably 0.01 mass parts or more relative to cyanate compound (A) 100 mass parts, more preferably 0.05 mass parts or more, further preferably 0.1 mass parts or more, more preferably 0.5 mass parts or more, and further preferably 0.8 mass parts or more.By being set to above the aforementioned lower limit, there is a tendency that the curing promotion effect is further improved.In addition, the upper limit of the content of the aforementioned amine adduct compound (B) is preferably 30 mass parts or less relative to cyanate compound (A) 100 mass parts, more preferably 20 mass parts or less, further preferably 10 mass parts or less, further preferably 5 mass parts or less, and further preferably 3 mass parts or less.By being set to below the aforementioned upper limit, there is a tendency that the stability during the storage of the resin composition is further improved.

[0118] The resin composition of the present embodiment may contain only one amine adduct compound (B) or two or more amine adduct compounds (B). When two or more amine adduct compounds (B) are contained, the total amount is preferably within the above range.

[0119] <Borate Ester (C)>

[0120] The resin composition of the present embodiment contains a boric acid ester (C). By containing a boric acid ester (C), a resin composition having excellent stability during storage and excellent curability during heating can be obtained.

[0121] In the present embodiment, the boric acid ester (C) is preferably a compound capable of suppressing the activity of the nitrogen atom contained in the amine adduct compound (B).

[0122] As the boric acid ester (C), a compound represented by the formula (C) is preferred.

[0123]

[0124] (In formula (C), each R is independently a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, and the hydrocarbon group may contain 1 or 2 or more oxygen atoms.)

[0125] Examples of the substituent that R may have include a hydroxyl group, an amino group, and a carboxyl group. These substituents may be present at the terminal of the hydrocarbon group or may be present in a part other than the terminal.

[0126] R is preferably an unsubstituted hydrocarbon group having 1 to 20 carbon atoms, more preferably an unsubstituted alkyl group having 1 to 10 carbon atoms (preferably a linear or branched alkyl group having 1 to 10 carbon atoms) or an unsubstituted aryl group having 6 to 12 carbon atoms (preferably a phenyl group).

[0127] The three Rs in formula (C) may be the same or different, but are preferably the same.

[0128] The molecular weight of the boric acid ester (C) used in the present embodiment is preferably 10 4 to 1500, more preferably 10 4 to 1000, further preferably 10 4 to 500, and further preferably 10 4 to 350.

[0129] Specific examples of the boric acid ester (C) used in the present embodiment include trimethyl borate, triethyl borate, tripropyl borate, triisopropyl borate, tributyl borate, tripentyl borate, triallyl borate, trihexyl borate, trioctyl borate, triisooctyl borate, trinonyl borate, tridecyl borate, tridodecyl borate, trihexadecyl borate, trioctadecyl borate, triphenyl borate, tricyclohexyl borate, trihexadecyl borate, triocta ... borate, tritolyl borate, triethanolamine borate, tri-o-phenylene bisboronate, bis-o-phenylene pyroborate, bis-2,3-dimethylethylene phenylene pyroborate, bis-2,2-dimethyltrimethylene pyroborate, tri(2-ethylhexyloxy)borane, bis(1,4,7,10-tetraoxaundecyl)(1,4,7,10,13-pentaoxatetradecyl)(1,4,7-trioxaundecyl)borane, 2 -(β-dimethylaminoisopropoxy)-4,5-dimethyl-1,3,2-dioxaborolane, 2-(β-diethylaminoethoxy)-4,4,6-trimethyl-1,3,2-dioxaborolane, 2-(β-dimethylaminoethoxy)-4,4,6-trimethyl-1,3,2-dioxaborolane, 2-(β-diisopropylaminoethoxy)-1,3,2-dioxaborolane , 2-(β-diisopropylaminoethoxy)-4-methyl-1,3,2-dioxaborinane, 2-(γ-dimethylaminopropoxy)-1,3,6,9-tetraoxa-2-borinane and 2-(β-dimethylaminoethoxy)-4,4-(4-hydroxybutyl)-1,3,2-dioxaborinane, 2,2-oxybis(5,5-dimethyl-1,3,2-dioxaborinane), etc.

[0130] The borate (C) content in the resin composition of the present embodiment is preferably 0.01 mass parts or more relative to cyanate compound (A) 100 mass parts, more preferably 0.05 mass parts or more, further preferably 0.08 mass parts or more, further preferably 0.1 mass parts or more, further preferably 0.2 mass parts or more, can be 0.4 mass parts or more.By being set to above-mentioned lower limit value or more, so that there is the tendency that the stability of resin composition and curability further improve.In addition, the upper limit value of the borate (C) content is preferably 15 mass parts or less relative to cyanate compound (A) 100 mass parts, more preferably 10 mass parts or less, further preferably 5 mass parts or less, further preferably 3 mass parts or less, further preferably 1 mass parts or less.By being set to below the above-mentioned upper limit value, so that there is the tendency that the stability of resin composition and the heat resistance of cured product further improve.

[0131] The resin composition of the present embodiment may contain only one type of boric acid ester (C), or may contain two or more types. When containing two or more types, it is preferred that the total amount falls within the above range.

[0132] The mass ratio of the amine adduct compound (B) to the boric ester (C) in the resin composition of the present embodiment (amine adduct compound (B) / boric ester (C)) is preferably 0.5 or more, more preferably 1.0 or more, and further preferably 1.5 or more. By setting it to be above the aforementioned lower limit, there is a tendency to more effectively improve the effect of the present invention. The mass ratio of the amine adduct compound (B) to the boric ester (C) (amine adduct compound (B) / boric ester (C)) is preferably 10.0 or less, more preferably 5.0 or less, and further preferably 3.5 or less. By setting it to be below the aforementioned upper limit and above the lower limit, there is a tendency to more effectively improve the effect of the present invention.

[0133] <Phenol compound (D)>

[0134] The resin composition of this embodiment preferably contains a phenol compound (D). When a phenol compound is contained, there is a tendency that the curability is further improved.

[0135] The phenol compound (D) in the present embodiment refers to a compound having a structure in which at least a hydroxyl group is directly bonded to a benzene ring, and preferably a compound having a structure in which at least a hydroxyl group is directly bonded to a benzene ring. In addition, the phenol compound (D) may be a low molecular weight or a high molecular weight. In addition, the benzene ring possessed by the phenol compound (D) may optionally have other substituents other than a hydroxyl group. When the aforementioned benzene ring has a substituent other than a hydroxyl group, each benzene ring preferably has 1 to 3 other substituents other than a hydroxyl group.

[0136] As other substituents, hydrocarbon groups having 1 to 20 carbon atoms, alkoxy groups having 1 to 20 carbon atoms, aryloxy groups having 6 to 20 carbon atoms, alkylcarbonyl groups having 1 to 20 carbon atoms, alkoxycarbonyl groups having 1 to 20 carbon atoms, arylcarbonyl groups having 6 to 20 carbon atoms, and halogen atoms can be exemplified. Preferably, hydrocarbon groups having 1 to 20 carbon atoms, alkoxy groups having 1 to 20 carbon atoms, aryloxy groups having 6 to 20 carbon atoms, alkylcarbonyl groups having 1 to 20 carbon atoms, alkoxycarbonyl groups having 1 to 20 carbon atoms, and arylcarbonyl groups having 6 to 20 carbon atoms are preferred, and hydrocarbon groups having 1 to 20 carbon atoms are more preferred. In addition, two other substituents bonded to the benzene ring may be bonded to each other to form a ring. As examples of two other substituents bonded to the benzene ring to form a ring, naphthalene rings, indane rings, etc. can be exemplified.

[0137] The phenol compound (D) used in the present embodiment is preferably a compound having a structure in which one or two hydroxyl groups are directly bonded to a benzene ring. Examples of the substituent include a hydrocarbon group (preferably an alkyl group) having 5 to 20 carbon atoms.

[0138] An example of the phenol compound (D) used in the present embodiment is a low molecular weight compound, for example, a compound having a molecular weight of 94 to 1000, preferably a compound having a molecular weight of 94 to 500.

[0139] Another example of the phenol compound (D) used in the present embodiment is a polymer compound, for example, a phenol compound having a molecular weight of more than 1,000 and not more than 100,000, preferably more than 1,000 and not more than 10,000.

[0140] Specific examples of the phenolic compound (D) used in the present embodiment include phenol, cresol, xylenol, ethylphenol, o-isopropylphenol, butylphenols such as p-tert-butylphenol, p-tert-octylphenol, nonylphenol, dinonylphenol, catechol, resorcinol, hydroquinone, trihydroxybenzene, styrenated phenol, hydroxybenzoic acid esters, thymol, p-naphthol, p-nitrophenol, p-chlorophenol, phenol novolac resin, cresol novolac resin, and xylenol novolac resin, preferably nonylphenol and dinonylphenol.

[0141] When the resin composition of the present embodiment includes a phenol compound (D), its content is preferably more than 1 mass part relative to cyanate compound (A) 100 mass parts, more preferably more than 2 mass parts, more preferably more than 3 mass parts, more preferably more than 4 mass parts, and more preferably more than 5 mass parts.By being set to more than the aforementioned lower limit, there is a tendency that curability is further improved.In addition, the upper limit of the content of the aforementioned phenol compound (D) is preferably less than 20 mass parts relative to cyanate compound (A) 100 mass parts, more preferably less than 17 mass parts, more preferably less than 14 mass parts, more preferably less than 12 mass parts, and more preferably less than 10 mass parts.By being set to less than the aforementioned upper limit, there is a tendency that the heat resistance of the cured product is further improved.

[0142] The resin composition of the present embodiment may contain only one phenol compound (D) or two or more phenol compounds (D). When containing two or more phenol compounds (D), the total amount is preferably within the above range.

[0143] <Toughness Imparting Agent (E)>

[0144] The resin composition of the present embodiment may contain a toughness imparting agent (E). By adding a toughness imparting agent (E), the toughness of the obtained cured product can be further improved.

[0145] As the toughening agent (E), resins can be exemplified. One example of the toughening agent (E) is a thermoplastic resin, and another example is a powdered resin.

[0146] As a thermoplastic resin, it is usually preferred that the main chain has a thermoplastic resin selected from a carbon-carbon bond, an amide bond, an imide bond, an ester bond, an ether bond, a carbonate bond, a carbamate bond, a thioether bond, a sulfone bond and a carbonyl bond, optionally partially having a cross-linked structure. In addition, it can have crystallinity or can be amorphous. In particular, it is preferably selected from at least one resin in the group consisting of polyamide resin, polycarbonate resin, polyacetal resin, polyphenylene oxide resin, polyphenylene sulfide resin, polyarylate resin, polyester resin, polyamide-imide resin, polyimide resin, polyetherimide resin, polyimide resin with phenyltrimethylindane structure, polysulfone resin, polyethersulfone resin, polyetherketone resin, polyetheretherketone resin, polyaramid resin, polyethernitrile resin and polybenzimidazole resin, more preferably polyimide resin.

[0147] As the polyimide resin, reference can be made to the description in paragraphs 0013 to 0021 of JP-A-2022-045273, the contents of which are incorporated herein by reference.

[0148] The powdered resin is preferably a powdered thermoplastic resin, and examples thereof include rubber powders such as styrene-based powders, butadiene-based powders, and acrylic-based powders; core-shell rubber powders; silicone-based powders, etc. Among these powdered resins, silicone-based powders are preferred because the rigidity of the resulting cured product is superior and warpage can be further reduced.

[0149] Examples of the silicone type powder include silicone resin powder, silicone rubber powder, and silicone composite powder, etc. Among these, silicone composite powder is preferred from the viewpoint of providing a cured product with better rigidity and further reducing warpage.

[0150] Examples of the silicone composite powder include KMP-600 (trade name), KMP-601 (trade name), KMP-602 (trade name), KMP-605 (trade name), and X-52-7030 (trade name) manufactured by Shin-Etsu Chemical Co., Ltd.

[0151] When the resin composition of the present embodiment includes a toughness imparting agent (E), its content is preferably more than 1 mass part relative to cyanate ester compound (A) 100 mass parts, more preferably more than 3 mass parts, more preferably more than 5 mass parts, more preferably more than 10 mass parts, and more preferably more than 15 mass parts. By being set to more than the aforementioned lower limit, there is a tendency that the toughness of the obtained cured product is further improved. In addition, the upper limit of the content of the aforementioned toughness imparting agent (E) is preferably less than 40 mass parts relative to cyanate ester compound (A) 100 mass parts, more preferably less than 38 mass parts, more preferably less than 33 mass parts, more preferably less than 30 mass parts, and can be less than 27 mass parts. By being set to less than the aforementioned upper limit, there is a tendency that the heat resistance of the cured product is further improved.

[0152] The resin composition of the present embodiment may contain only one toughness imparting agent (E) or two or more thereof. When containing two or more thereof, the total amount is preferably within the above range.

[0153] <Other thermosetting resins>

[0154] The resin composition of the present embodiment may include other thermosetting resins except cyanate compound (A), or may not contain. As other thermosetting resins, epoxy resins, maleimide resins, phenolic resins, polyphenylene ether resins, benzoxazine resins, organic group-modified silicones, alkenyl-substituted nadic imide compounds, and resins with polymerizable carbon-carbon unsaturated groups can be exemplified. Their details can be referred to in International Publication No. 2022 / 034872, paragraphs 0020 to 0028, paragraphs 0054 to 0056, and paragraphs 0067 to 0070, the records of paragraphs 0036 to 0070 of Japanese Patent Publication No. 2022-000506, and the records of paragraphs 0049 to 0057 of Japanese Patent Publication No. 2022-046517, and these contents are cited in this specification.

[0155] When the resin composition of the present embodiment contains other thermosetting resins in addition to the cyanate compound (A), the content thereof is preferably 5 to 30 parts by mass based on 100 parts by mass of the resin solid content contained in the resin composition.

[0156] In addition, the resin composition of the present embodiment can be set to be substantially free of other thermosetting resins except the cyanate compound (A). Substantially free means: less than 5 parts by mass, preferably 3 parts by mass or less, more preferably 1 part by mass or less, and further preferably 0.1 parts by mass or less relative to 100 parts by mass of the resin solid content contained in the resin composition.

[0157] <Other ingredients>

[0158] The resin composition of the present embodiment may include filler (including inorganic filler, organic filler, filler, etc.), silane coupling agent, wetting dispersant, solvent, etc., in addition to the above-mentioned components. In addition, impact resistance improver, curing accelerator, flame retardant, conductivity imparting agent, crystal nucleating agent, ultraviolet absorber, antioxidant, shock absorber, antibacterial agent, insect repellent, deodorant, anti-coloring agent, heat stabilizer, mold release agent, antistatic agent, plasticizer, lubricant, colorant, pigment, dye, foaming agent, foaming agent, etc. may be mixed. Their details can be referred to the records of paragraphs 0057 to 0052 of Japanese Patent Publication No. 2021-195389 and paragraphs 0040 to 0048 of Japanese Patent Publication No. 2022-046517, and these contents are cited in this specification.

[0159] In the case where the resin composition of the present embodiment includes a filler, it is preferably included in a ratio of 10 to 500 parts by mass relative to 100 parts by mass of the resin solid content. In addition, the resin composition of the present embodiment can also be set to a structure that does not substantially contain a filler. Substantially free of a filler means that the content of the filler in the resin composition is less than 10 parts by mass relative to 100 parts by mass of the resin solid content, preferably 5 parts by mass or less, more preferably 3 parts by mass or less, and further preferably 1 part by mass or less.

[0160] <Physical Properties of Resin Composition>

[0161] The viscosity of the resin composition of the present embodiment at 80°C is preferably 0.05 to 50 Pa·s. By setting such a viscosity, it can be preferably used as various materials. The viscosity of the resin composition of the present embodiment at 80°C is more preferably 0.10 Pa·s or more, and is preferably 40 Pa·s or less, more preferably 30 Pa·s or less, more preferably 20 Pa·s or less, more preferably 10 Pa·s or less, and even more preferably 8 Pa·s or less.

[0162] In particular, when the resin composition of the present embodiment is used for a prepreg, the viscosity at 80° C. is preferably 0.1 Pa·s or more, more preferably 2 Pa·s or more, and is preferably 10 Pa·s or less, more preferably 8 Pa·s or less.

[0163] The above viscosity is measured according to the description in the Examples described below.

[0164] The resin composition of the present embodiment preferably has excellent stability during storage. For example, when the viscosity of each composition is kept at 80° C. for 60 minutes, when expressed in the form of relative viscosity when the viscosity before the start of the test is set to 100, it is preferably 180 or less, more preferably 150 or less, further preferably 140 or less, further preferably 130 or less, and further preferably 120 or less. The lower limit of the relative viscosity is preferably 100, and even if it is 101 or more, the performance requirements will be fully met.

[0165] The relative viscosity is measured according to the description in the examples described later.

[0166] The resin composition of the present embodiment preferably has excellent curing properties. For example, using a differential scanning calorimeter, under the measurement conditions of a start temperature of 40°C, an end temperature of 380°C, and a heating rate of 3°C / minute, the exothermic behavior of each composition is observed, and the peak top temperature is preferably 185°C or less, more preferably 180°C or less, further preferably 175°C or less, further preferably 170°C or less, and further preferably 165°C or less. In addition, the lower limit of the peak top temperature is preferably 100°C or more, more preferably 110°C or more, further preferably 120°C or more, further preferably 130°C or more, and further preferably 135°C or more.

[0167] The peak top temperature is measured according to the description in the examples described later.

[0168] The resin composition of the present embodiment preferably has high heat resistance. For example, the glass transition temperature of the cured product obtained by heating the resin composition of the present embodiment at 135°C for 8 hours and then at 177°C for 4 hours is preferably 180°C or more, more preferably 184°C or more, further preferably 190°C or more, further preferably 195°C or more, and further preferably 200°C or more. On the other hand, the upper limit of the glass transition temperature is not particularly limited, and 300°C or less is practical, and even if it is 250°C or less, the required performance will be fully met.

[0169] Regarding the glass transition temperature (Tg), the storage modulus G' of the cured product of the resin composition was measured by a DMA method using a dynamic viscoelasticity analyzer in accordance with JIS C6481, and the initial (onset) value was defined as the glass transition temperature (Tg).

[0170] The details were measured according to the description in the examples described later.

[0171] <Purpose>

[0172] The resin composition of the present embodiment can be suitably used as a cured product, a prepreg, a multilayer body, a sealing material, an adhesive, an insulating material, a coating material, or a fiber-reinforced composite material. These will be described below.

[0173] <<Cured product>>

[0174] The cured product of the present embodiment is a cured product of the resin composition of the present embodiment. There is no particular limitation on the method for manufacturing the cured product, and the cured product can be obtained by, for example, melting the resin composition or dissolving it in a solvent, flowing it into a mold, and curing it under normal conditions using heat, light, etc. In the case of thermal curing, the curing temperature is not particularly limited, and is preferably within the range of 120 to 300° C. from the viewpoint of effectively curing and preventing the degradation of the obtained cured product. In the case of photocuring, the wavelength region of the light is not particularly limited, and preferably, curing occurs within the range of 100 to 500 nm, which is effectively cured by a photopolymerization initiator, etc.

[0175] <<Prepreg>>

[0176] The prepreg of the present embodiment is a prepreg formed by a substrate and a resin composition of the present embodiment. More specifically, the prepreg of the present embodiment has a substrate, and a resin composition and / or a cured product thereof applied (e.g., impregnated or coated) to the aforementioned substrate. That is, in the aforementioned prepreg, the resin composition may be uncured or may be a cured product comprising a semi-cured product. In addition, the solvent may be removed from the resin composition.

[0177] The method for producing the prepreg can be carried out according to a conventional method and is not particularly limited.

[0178] For example, the resin composition of the present embodiment can be applied (preferably coated) to a substrate to make a prepreg. At this time, the resin composition can be heated and coated on the substrate, and then returned to room temperature, or a solvent can be added to the resin composition and coated on the substrate, and then the solvent can be removed.

[0179] Alternatively, the prepreg of the present embodiment can be produced by, for example, applying the resin composition of the present embodiment to a substrate and then semi-curing (bringing it to a B-stage) by heating it in a dryer at 100 to 200° C. for 1 to 30 minutes.

[0180] The total amount of the resin solid content and the filler in the resin composition is preferably 30% by mass or more, more preferably 35% by mass or more, and further preferably 40% by mass or more relative to the total amount of the prepreg, and is preferably 90% by mass or less, more preferably 85% by mass or less, and further preferably 80% by mass or less. By making the content of the resin composition within the above range, there is a tendency that the moldability of the prepreg is further improved.

[0181] The substrate of the prepreg is not particularly limited and can be appropriately selected and used according to the target application and performance. Specific examples of the fibers constituting the substrate are not particularly limited, and include glass fibers such as E glass, D glass, S glass, Q glass, spherical glass, NE glass, L glass, and T glass; inorganic fibers other than glass such as quartz fiber, carbon fiber, boron fiber, and basalt fiber; wholly aromatic polyamides such as poly(p-phenylene terephthalamide) (Kevlar (registered trademark), manufactured by DuPont), copoly(p-phenylene terephthalamide) (Technora (registered trademark), manufactured by Teijin Techno Products Limited); polyesters such as 2,6-hydroxynaphthoic acid and p-hydroxybenzoic acid (Vectran (registered trademark), manufactured by Kuraray Co., Ltd.), Zxion (registered trademark, manufactured by KB SEIREN, LTD.); organic fibers such as poly(p-phenylene benzoxazole) (Xyron (registered trademark), manufactured by Toyobo Co., Ltd.) and polyimide. Among these, at least one selected from the group consisting of carbon fibers and / or glass fibers is preferred, and carbon fibers are more preferred. These substrates may be used alone or in combination of two or more.

[0182] The shape of the substrate is not particularly limited, and examples thereof include woven fabrics, nonwoven fabrics, rovings, chopped strand mats, surface mats, etc. As the weaving method of the woven fabric, there is no particular limitation, and for example, plain weave, basket weave, twill weave, etc. are known, and can be appropriately selected from these known ones according to the target use and performance. In addition, it is suitable to use materials obtained by fiber opening treatment and glass woven fabrics obtained by surface treatment using silane coupling agents, etc. The thickness and mass of the substrate are not particularly limited, and materials of about 0.01 to 0.3 mm are generally suitable. In particular, from the viewpoint of strength and water absorption, the substrate is preferably a woven fabric of glass fiber and / or carbon fiber.

[0183] The multilayer body of the present embodiment is formed by the prepreg of the present embodiment. The multilayer body of the present embodiment is preferably obtained by overlapping two or more layers of the above-mentioned prepreg. In the multilayer body of the present embodiment, the resin composition in the prepreg may be uncured or may be a cured product including a semi-cured product.

[0184] The multilayer body of the present embodiment may have other constituent layers within the range not exceeding the resin of the present embodiment.

[0185] The prepreg and the multilayer body of the present embodiment can be preferably used as materials for aerospace applications.

[0186] <<Sealing Materials>>

[0187] The sealing material of the present embodiment comprises the resin composition of the present embodiment. As the manufacturing method of the sealing material, known methods can usually be appropriately applied, without particular limitation. For example, the sealing material can be manufactured by mixing the above-mentioned resin composition with various known additives or solvents commonly used in the sealing material application using a known agitator. It should be noted that the addition method of each component during mixing can usually be appropriately applied by known methods, without particular limitation.

[0188] <<Adhesive>>

[0189] The adhesive of the present embodiment includes the resin composition of the present embodiment. As the manufacturing method of the adhesive, known methods can usually be appropriately applied, without particular limitation. For example, the above-mentioned resin composition can be mixed with various known additives or solvents commonly used in adhesive applications by using a known agitator to manufacture the adhesive. It should be noted that the addition method of each component during mixing can usually be appropriately applied by known methods, without particular limitation.

[0190] <<Insulation Materials>>

[0191] The insulating material of the present embodiment includes the resin composition of the present embodiment. As the manufacturing method of the insulating material, generally known methods can be appropriately applied, without particular limitation. For example, the insulating material can be manufactured by mixing the above-mentioned resin composition with various known additives or solvents commonly used in the insulating material application using a known agitator. It should be noted that the adding method of each component during mixing can generally be appropriately applied by known methods, without particular limitation.

[0192] <<Paint>>

[0193] The coating of the present embodiment includes the resin combination of the present embodiment. As the manufacturing method of the coating, known methods can usually be appropriately applied, without particular limitation. For example, the coating can be manufactured by mixing the above-mentioned resin combination with various known additives or solvents commonly used in coating applications using a known agitator. It should be noted that the addition method of each component during mixing can usually be appropriately applied by known methods, without particular limitation.

[0194] <<Fiber-reinforced composite materials>>

[0195] The fiber-reinforced composite material of the present embodiment comprises reinforcing fibers and a cured product of the resin composition of the present embodiment, preferably reinforcing fibers and a cured product obtained by applying (preferably impregnating or coating) the resin composition to the reinforcing fibers and curing the reinforcing fibers.

[0196] As reinforcing fibers, known materials can usually be used, without particular limitation. As specific examples thereof, glass fibers such as E glass, D glass, L glass, S glass, T glass, Q glass, UN glass, NE glass, and spherical glass can be cited; carbon fibers, aramid fibers, boron fibers, PBO fibers, high-strength polyethylene fibers, alumina fibers, and silicon carbide fibers, etc., can be used. Regarding the form and arrangement of reinforcing fibers, there are no particular limitations, and they can be appropriately selected from textiles, non-woven fabrics, felts, knitted fabrics, cords, unidirectional strands, rovings, chopped strands, etc. In addition, as the form of reinforcing fibers, preforms (preforms) (those obtained by laminating a textile base fabric formed by reinforcing fibers, or objects obtained by suturing and integrating them with sutures, or fiber structures such as three-dimensional textiles and braids) can also be applied.

[0197] As the manufacturing method of these fiber reinforced composite materials, known methods can usually be appropriately applied, without particular limitation. As its specific example, liquid composite material molding method, resin film infiltration method, fiber winding method, manual reinforced plastic film method, pultrusion method, etc. can be listed. Among them, the resin transfer molding method as one of the liquid composite material molding methods can be used for various purposes because the raw materials other than prefabricated products such as metal plates, foam cores, and honeycomb cores can be pre-arranged in the molding mold, and therefore, it is preferably used in the case of mass production of composite materials with relatively complex shapes in a short time.

[0198] Example

[0199] Below, enumerate embodiment, more specifically illustrate the present invention.The material, dosage, ratio, processing content, processing step etc. shown in the following embodiment can be appropriately changed within the scope not exceeding the gist of the present invention.Therefore, the scope of the present invention is not limited to the specific example shown below.

[0200] If the measuring equipment used in the examples is difficult to obtain due to the model being obsolete, other equipment with equivalent performance may be used for the measurement.

[0201] <Synthesis Example 1 Synthesis of Cyanate (SNCN)>

[0202] In a reactor, 0.47 mol (OH group conversion) of α-naphthol aralkyl type phenolic resin (product name: SN495V, OH group equivalent: 236 g / eq., manufactured by NIPPON STEEL Chemical & Material Co., Ltd., containing naphthol aralkyl repeating unit number n of 1 to 5) was dissolved in 500 mL of chloroform, and 0.7 mol of triethylamine was added to the solution. While maintaining the temperature at -10°C, 300 g of chloroform solution of 0.93 mol of cyanogen chloride was added dropwise to the reactor over 1.5 hours, and after the addition was completed, the mixture was stirred for 30 minutes. Thereafter, a mixed solution of 0.1 mol of triethylamine and 30 g of chloroform was further added dropwise to the reactor, and the reaction was completed by stirring for 30 minutes. After filtering out the by-produced triethylamine hydrochloride from the reaction solution, the obtained filtrate was washed with 500 mL of 0.1N hydrochloric acid, and then washed with 500 mL of water was repeated 4 times. After drying with sodium sulfate, it was evaporated at 75°C and further degassed under reduced pressure at 90°C to obtain a brown solid α-naphthol aralkyl type cyanate resin (hereinafter referred to as SNCN). The obtained α-naphthol aralkyl type cyanate resin was analyzed by infrared absorption spectroscopy, and the results showed that 2264 cm -1 Absorption of nearby cyanate groups.

[0203] <Synthesis Example 2 Synthesis of Cyanate Ester (P-2M)>

[0204] In a reactor, 0.5 mol (OH group conversion) of bisphenol M (OH group equivalent: 173 g / eq., manufactured by MITSUI FINE CHEMICALS, INC Co., Ltd.) was dissolved in 500 mL of chloroform, and 0.75 mol of triethylamine was added to the solution. While maintaining the temperature at -10°C, 300 g of a chloroform solution of 1.0 mol of cyanogen chloride was dripped into the reactor over 1.5 hours, and after the dripping was completed, the mixture was stirred for 30 minutes. Thereafter, a mixed solution of 0.1 mol of triethylamine and 30 g of chloroform was further dripped into the reactor, and the reaction was completed by stirring for 30 minutes. After filtering out the by-produced hydrochloride of triethylamine from the reaction solution, the obtained filtrate was washed with 500 mL of 0.1N hydrochloric acid, and then washed with 500 mL of water was repeated 4 times. After drying with sodium sulfate, it was evaporated at 75°C and further degassed under reduced pressure at 90°C to obtain a pale yellow solid bis-M-type cyanate resin (hereinafter referred to as P-2M). The obtained bis-M-type cyanate resin was analyzed by infrared absorption spectroscopy, and the peak at 2234 cm -1 and 2270cm -1 Absorption of nearby cyanate groups.

[0205] <Preparation of Composition>

[0206] Example 1

[0207] 50 parts by mass of SNCN obtained in Synthesis Example 1 as the cyanate ester compound (A), 50 parts by mass of bisphenol A type cyanate (trade name: TA manufactured by Mitsubishi Gas Chemical Co., Ltd.), 1 part by mass of AJICURE PN-50 (softening temperature: 110° C., manufactured by Ajinomoto Fine-Techno Co., Inc.) as the amine adduct compound (B), 0.5 parts by mass of triethyl borate (manufactured by Tokyo Chemical Industry Co., Ltd.) as the borate ester (C), and 6 parts by mass of 4-nonylphenol (manufactured by Tokyo Chemical Industry Co., Ltd.) as the phenol compound (D) were placed in a screw-capped vial, heated, stirred and mixed to obtain a composition.

[0208] Example 2

[0209] In Example 1, a composition was obtained in the same manner as in Example 1 except that 0.5 parts by mass of triphenyl borate (manufactured by Tokyo Chemical Industry Co., Ltd.) was used instead of 0.5 parts by mass of triethyl borate.

[0210] Example 3

[0211] In Example 1, a composition was obtained in the same manner as in Example 1 except that 1 part by mass of AJICURE MY-25 (softening temperature: 130° C., manufactured by Ajinomoto Fine-Techno Co., Inc.) was used instead of 1 part by mass of AJICURE PN-50.

[0212] Example 4

[0213] In Example 3, a composition was obtained in the same manner as in Example 3 except that 0.5 parts by mass of triphenyl borate was used instead of 0.5 parts by mass of triethyl borate.

[0214] Example 5

[0215] In Example 1, a composition was obtained in the same manner as in Example 1 except that 6 parts by mass of 2,4-dinonylphenol (manufactured by Yokkaichi Chemical Co., Ltd.) was used instead of 6 parts by mass of 4-nonylphenol.

[0216] Example 6

[0217] A composition was obtained in the same manner as in Example 1 except that 8 parts by mass of 4-nonylphenol was used instead of 6 parts by mass of 4-nonylphenol.

[0218] Example 7

[0219] A composition was obtained in the same manner as in Example 1 except that 10 parts by mass of 4-nonylphenol was used instead of 6 parts by mass of 4-nonylphenol.

[0220] Example 8

[0221] In Example 1, the same operation as in Example 1 was carried out to obtain a composition, except that 70 parts by mass of a prepolymer of bisphenol A cyanate (trade name: TA-1500, manufactured by Mitsubishi Gas Chemical Co., Ltd.) and 30 parts by mass of TA were used instead of 50 parts by mass of SNCN and 50 parts by mass of TA, 0.15 parts by mass of triethyl borate was used instead of 0.5 parts by mass of triethyl borate, and 10 parts by mass of 4-nonylphenol was used instead of 6 parts by mass of 4-nonylphenol.

[0222] Example 9

[0223] In Example 8, a composition was obtained in the same manner as in Example 8 except that 0.3 parts by mass of triethyl borate was used instead of 0.15 parts by mass of triethyl borate.

[0224] Example 10

[0225] In Example 8, a composition was obtained in the same manner as in Example 8 except that 0.5 parts by mass of triethyl borate was used instead of 0.15 parts by mass of triethyl borate.

[0226] Embodiment 11

[0227] In Example 8, a composition was obtained in the same manner as in Example 8 except that 0.7 parts by mass of triethyl borate was used instead of 0.15 parts by mass of triethyl borate.

[0228] Example 12

[0229] In Example 8, a composition was obtained in the same manner as in Example 8 except that 0.9 parts by mass of triethyl borate was used instead of 0.15 parts by mass of triethyl borate.

[0230] Embodiment 13

[0231] In Example 8, a composition was obtained in the same manner as in Example 8 except that 0.5 parts by mass of AJICURE PN-50 was used instead of 1 part by mass of AJICURE PN-50 and 6 parts by mass of 4-nonylphenol was used instead of 10 parts by mass of 4-nonylphenol.

[0232] Embodiment 14

[0233] In Example 13, a composition was obtained in the same manner as in Example 13 except that 1.5 parts by mass of AJICURE PN-50 was used instead of 0.5 parts by mass of AJICURE PN-50 and 0.45 parts by mass of triethyl borate was used instead of 0.15 parts by mass of triethyl borate.

[0234] Embodiment 15

[0235] In Example 1, a composition was obtained in the same manner as in Example 1 except that 25 parts by mass of a thermoplastic polyimide resin (trade name: Therplim, manufactured by Mitsubishi Gas Chemical Co., Ltd.) was added as a toughness imparting agent (E).

[0236] Example 16

[0237] In Example 1, a composition was obtained in the same manner as in Example 1 except that 65 parts by mass of SNCN and 35 parts by mass of P-2M obtained in Synthesis Example 2 were used instead of 50 parts by mass of SNCN and 50 parts by mass of TA.

[0238] Embodiment 17

[0239] In Example 8, the same operation as in Example 8 was carried out to obtain a composition, except that 90 parts by mass of a prepolymer of bisphenol A cyanate ester and 10 parts by mass of TA were used instead of 70 parts by mass of a prepolymer of bisphenol A cyanate ester and 30 parts by mass of TA, 0.4 parts by mass of triethyl borate was used instead of 0.15 parts by mass of triethyl borate, and 9 parts by mass of 4-nonylphenol was used instead of 10 parts by mass of 4-nonylphenol.

[0240] Embodiment 18

[0241] In Example 17, 85 parts by mass of a prepolymer of bisphenol A cyanate ester and 15 parts by mass of TA were used instead of 90 parts by mass of a prepolymer of bisphenol A cyanate ester and 10 parts by mass of TA, and 20 parts by mass of Therplim was added as a toughening agent (E). A composition was obtained in the same manner as in Example 17.

[0242] Embodiment 19

[0243] In Example 18, a composition was obtained in the same manner as in Example 18, except that 0.5 parts by mass of triethyl borate was used instead of 0.4 parts by mass of triethyl borate.

[0244] Embodiment 20

[0245] In Example 18, a composition was obtained in the same manner as in Example 18, except that 0.6 parts by mass of triethyl borate was used instead of 0.4 parts by mass of triethyl borate.

[0246] Embodiment 21

[0247] In Example 18, a composition was obtained in the same manner as in Example 18, except that 0.7 parts by mass of triethyl borate was used instead of 0.4 parts by mass of triethyl borate.

[0248] Embodiment 22

[0249] In Example 18, a composition was obtained in the same manner as in Example 18, except that 1 part by mass of triethyl borate was used instead of 0.4 parts by mass of triethyl borate.

[0250] Embodiment 23

[0251] In Example 18, a composition was obtained in the same manner as in Example 18 except that 20 parts by mass of silicone composite powder (trade name: KMP-600, manufactured by Shin-Etsu Chemical Co., Ltd.) was used instead of 20 parts by mass of Therplim.

[0252] Embodiment 24

[0253] In Example 18, a composition was obtained in the same manner as in Example 18 except that 20 parts by mass of silicone composite powder (trade name: KMP-601, manufactured by Shin-Etsu Chemical Co., Ltd.) was used instead of 20 parts by mass of Therplim.

[0254] Embodiment 25

[0255] In Example 18, a composition was obtained in the same manner as in Example 18 except that 20 parts by mass of silicone composite powder (trade name: KMP-602, manufactured by Shin-Etsu Chemical Co., Ltd.) was used instead of 20 parts by mass of Therplim.

[0256] Embodiment 26

[0257] In Example 18, a composition was obtained in the same manner as in Example 18 except that 20 parts by mass of silicone composite powder (trade name: KMP-605, manufactured by Shin-Etsu Chemical Co., Ltd.) was used instead of 20 parts by mass of Therplim.

[0258] Comparative Example 1

[0259] A composition was obtained in the same manner as in Example 1 except that 0.5 parts by mass of triethyl borate was not used.

[0260] Comparative Example 2

[0261] In Example 3, except that 0.5 parts by mass of triethyl borate was not used, the same operation as in Example 3 was carried out to obtain a composition.

[0262] Comparative Example 3

[0263] A composition was obtained in the same manner as in Example 1 except that 1 part by mass of AJICURE PN-50 was not used.

[0264] Comparative Example 4

[0265] In Example 2, a composition was obtained in the same manner as in Example 2 except that 1 part by mass of AJICURE PN-50 was not used.

[0266] Comparative Example 5

[0267] A composition was obtained in the same manner as in Example 1 except that 1 part by mass of AJICURE PN-50, 0.5 parts by mass of triethyl borate, and 6 parts by mass of nonylphenol were not used.

[0268] Comparative Example 6

[0269] A composition was obtained in the same manner as in Example 1 except that 1 part by mass of AJICURE PN-50 and 0.5 part by mass of triethyl borate were not used.

[0270] Comparative Example 7

[0271] In Example 8, a composition was obtained in the same manner as in Example 8 except that 0.15 parts by mass of triethyl borate was not used.

[0272] Comparative Example 8

[0273] In Example 16, a composition was obtained in the same manner as in Example 16 except that 0.5 parts by mass of triethyl borate was not used.

[0274] Comparative Example 9

[0275] In Comparative Example 8, a composition was obtained in the same manner as in Comparative Example 8 except that 0.1 parts by mass of cobalt (III) acetylacetonate (manufactured by Tokyo Chemical Industry Co., Ltd.) was used instead of 1 part by mass of AJICURE PN-50.

[0276] <Evaluation of Composition>

[0277] For each composition obtained as described above, various properties were evaluated according to the following criteria.

[0278] (1) Viscosity

[0279] The viscosity (unit: Pa·s) of each composition at 80° C. was measured using a dynamic viscoelasticity analyzer.

[0280] As a dynamic viscoelasticity analyzer, Discovery HR-2, manufactured by TA Instruments, was used.

[0281] (2) Stability

[0282] The viscosity of each composition was measured by using a dynamic viscoelasticity analyzer when it was kept at 80° C. for 60 minutes. The relative viscosity after 60 minutes from the start of the test was calculated by setting the viscosity before the start of the test as 100 to evaluate the stability.

[0283] As a dynamic viscoelasticity analyzer, Discovery HR-2, manufactured by TA Instruments, was used.

[0284] (3) Curing

[0285] Using a differential scanning calorimeter, the exothermic behavior of each composition was observed under measurement conditions of a start temperature of 40°C, an end temperature of 380°C, and a heating rate of 3°C / min, and the peak top temperature (unit: °C) was determined to evaluate curability.

[0286] As a differential scanning calorimeter, DSC7020 manufactured by SII Nanotechnologies was used.

[0287] (4) Heat resistance of cured product

[0288] About 6 g of each composition obtained as described above was weighed into an aluminum cup, and heated in a curing oven at 135° C. for 8 hours and further at 177° C. for 4 hours to obtain a cured product.

[0289] The obtained cured product was used to measure the storage modulus G' by the DMA method using a dynamic viscoelasticity analyzer in accordance with JIS C6481, and the initial value was defined as the glass transition temperature (Tg, unit: °C) to evaluate the heat resistance of the cured product.

[0290] As a dynamic viscoelasticity analyzer, Discovery HR-2, manufactured by TA Instruments, was used.

[0291] [Table 1]

[0292]

[0293] [Table 2]

[0294]

[0295] [Table 3]

[0296]

[0297] [Table 4]

[0298]

[0299] [Table 5]

[0300]

[0301] [Table 6]

[0302]

[0303] It can also be clearly confirmed from Tables 1 to 6 that the resin composition obtained using the cyanate compound (A), the amine adduct (B) and the borate (C) of the present invention has stability and curability, and its cured product has excellent heat resistance (high glass transition temperature).

Claims

1. A resin composition comprising a cyanate compound (A), an amine adduct compound (B) and a borate ester (C).

2. The resin composition according to claim 1, wherein The cyanate compound (A) comprises at least one selected from the group consisting of a compound represented by the following formula (I) and a compound represented by the following formula (II), In formula (I), Ar1 each independently represents an aromatic ring; Ra each independently represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, an aryl group having 6 to 12 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms, and the alkyl group or aryl group in Ra optionally has a substituent; a represents the number of bonds of the cyano group bonded to Ar1, and each independently represents an integer of 1 to 3; b represents the number of bonds of Ra bonded to Ar1, and each independently represents the number obtained by subtracting (a+2) from the number of substitutable groups of Ar1; c is an integer of 1 to 50; X each independently represents a single bond, a divalent organic group having 1 to 50 carbon atoms, a sulfonyl group (-SO2-), a divalent sulfur atom (-S-), or a divalent oxygen atom (-O-), In formula (II), Ar2 represents an aromatic ring; Rb each independently represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 12 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms; the alkyl group or aryl group in Rb optionally has a substituent; d represents the number of bonds of the cyano group bonded to Ar2, which is an integer of 2 to 3; e represents the number of bonds of Rb bonded to Ar2, which is the number obtained by subtracting (d+2) from the number of substitutable groups of Ar2.

3. The resin composition according to claim 2, wherein Each of X in the formula (I) independently represents a divalent linking group selected from the group consisting of the following formulae (III) to (XIV), In formula (III), Ar3 each independently represents an aromatic ring; Rc, Rd, Rg and Rh each independently represent a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or an aryl group having 6 to 12 carbon atoms, and the alkyl group or aryl group in Rc, Rd, Rg and Rh may optionally have a substituent; Re and Rf each independently represent a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 12 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms, and the alkyl group or aryl group in Re and Rf may optionally have a substituent; f represents an integer from 0 to 5, In formula (IV), Ar4 each independently represents an aromatic ring; Ri and Rj each independently represent a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 12 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms, and the alkyl group or aryl group in Ri and Rj may have a substituent; g represents an integer of 0 to 5, In the formula (VIII), h represents an integer of 4 to 7; and in the formula (XIII), Rk each independently represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.

4. The resin composition according to any one of claims 1 to 3, wherein The cyanate compound (A) comprises at least one selected from the group consisting of a compound represented by the following formula (XV) and a compound represented by the following formula (XVI), In formula (XV), Ar5 each independently represents an aromatic ring; Rl each independently represents a methylene group, a methyleneoxy group, a methyleneoxymethylene group or an oxymethylene group, and a group obtained by linking two or more of these groups; Rm and Rn each independently represent a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 12 carbon atoms or an alkoxy group having 1 to 4 carbon atoms, and the alkyl group or aryl group in Rm and Rn optionally has a substituent; i represents the number of bonds of the cyano group bonded to Ar5, which is an integer of 1 to 3; j represents the number of bonds of Rm bonded to Ar5, which is a number obtained by subtracting (i+2) from the number of substitutable groups of Ar5; k represents the number of bonds of Rn bonded to Ar5, which is a number obtained by subtracting 2 from the number of substitutable groups of Ar5; l represents an integer greater than 1; m represents an integer greater than 1; the arrangement of each repeating unit is arbitrary, In formula (XVI), Ar6 each independently represents an aromatic ring; Ro each independently represents a methylene group, a methyleneoxy group, a methyleneoxymethylene group or an oxymethylene group, or a group obtained by linking them; Rp and Rq each independently represent a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 12 carbon atoms or an alkoxy group having 1 to 4 carbon atoms, and the alkyl group or aryl group in Rp and Rq optionally has a substituent; n represents the number of bonds of the cyano group bonded to Ar6, which is an integer of 2 to 3; o represents the number of bonds of Rp bonded to Ar6, which is the number obtained by subtracting (n+2) from the number of substitutable groups of Ar6; p represents the number of bonds of Rq bonded to Ar6, which is the number obtained by subtracting 2 from the number of substitutable groups of Ar6; q represents an integer greater than 1.

5. The resin composition according to any one of claims 1 to 4, wherein The content of the amine adduct compound (B) is 0.01 to 30 parts by mass based on 100 parts by mass of the cyanate compound (A).

6. The resin composition according to any one of claims 1 to 5, wherein The content of the boric acid ester (C) is 0.01 to 15 parts by mass based on 100 parts by mass of the cyanate ester compound (A). 7 . The resin composition according to claim 1 , further comprising a phenol compound (D).

8. The resin composition according to claim 7, wherein The content of the phenol compound (D) is 1 to 20 parts by mass based on 100 parts by mass of the cyanate compound (A). 9 . The resin composition according to claim 1 , further comprising a toughening agent (E).

10. The resin composition according to claim 9, wherein The toughening agent (E) contains a thermoplastic resin.

11. The resin composition according to claim 9 or 10, wherein The toughening agent (E) contains a powdery resin.

12. The resin composition according to any one of claims 9 to 11, wherein The content of the toughening agent (E) is 1 to 40 parts by mass based on 100 parts by mass of the cyanate compound (A).

13. The resin composition according to any one of claims 1 to 11, wherein The content of the amine adduct compound (B) is 0.01 to 30 parts by mass relative to 100 parts by mass of the cyanate compound (A). The content of the boric acid ester (C) is 0.01 to 15 parts by mass relative to 100 parts by mass of the cyanate ester compound (A). The resin composition further comprises a phenol compound (D), The content of the phenol compound (D) is 1 to 20 parts by mass based on 100 parts by mass of the cyanate compound (A). 14 . The resin composition according to claim 13 , further comprising a toughening agent (E), wherein the content of the toughening agent (E) is 1 to 40 parts by mass based on 100 parts by mass of the cyanate compound (A). 15 . A cured product, which is a cured product of the resin composition according to claim 1 . 16 . A sealing material comprising the resin composition according to claim 1 . 17 . An adhesive comprising the resin composition according to claim 1 . 18 . An insulating material comprising the resin composition according to claim 1 .

19. A coating material comprising the resin composition according to any one of claims 1 to 14. 20 . A prepreg comprising a base material and the resin composition according to claim 1 .

21. A multilayer body formed from the prepreg according to claim 20.

22. A fiber-reinforced composite material comprising reinforcing fibers and a cured product of the resin composition according to any one of claims 1 to 14.

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