Composition, cured product, and adhesive agent

Abstract

The purpose of the present invention is to provide a composition that can form a cured product having an excellent balance between electrical characteristics and adhesive strength, and that has excellent storage stability.　The present invention pertains to a composition comprising a styrene-based elastomer (A) and a radically polymerizable compound (B). The radically polymerizable compound (B) includes a modified polyphenylene ether (B1) having an ethylenically unsaturated bond-containing group at a terminal, and a compound (B2) containing an alkoxysilyl group and an ethylenically unsaturated bond.　Preferably, the contained amount of the styrene-based elastomer (A) is 100-1,000 parts by mass with respect to 100 parts by mass of the modified polyphenylene ether (B1) having an ethylenically unsaturated bond at a terminal, and the contained amount of the compound (B2) containing an alkoxysilyl group and an ethylenically unsaturated bond is 1.1-10 parts by mass in a total of 100 parts by mass of the styrene-based elastomer (A) and the radically polymerizable compound (B).

Description

Composition, cured product, and adhesive

[0001] The present invention relates to a composition, a cured product thereof, and an adhesive.

[0002] In the information and communications field, the increasing performance and functionality of electrical and electronic devices is driving the need for high-speed information communication. For example, 5G (fifth-generation mobile communications system) high-speed communication services began in 2020. 5G uses high-frequency radio waves in the "millimeter wave" band (wavelength 1-10 mm, frequency 30-300 GHz). Millimeter waves can transmit large volumes of data at high speeds in a single transmission, and are capable of communications characterized by multiple simultaneous connections and ultra-low latency. As such, 5G is expected to be an essential infrastructure for realizing an IoT society in which all "things" are connected to the Internet.

[0003] On the other hand, when a high-frequency digital signal such as the millimeter wave is transmitted through a circuit board, a portion of the transmitted digital signal is thermally converted in the dielectric of the circuit board wiring, causing dielectric loss, resulting in an attenuated digital signal reaching the receiving end, a phenomenon known as "transmission loss." The dielectric loss depends on the electrical properties of the dielectric, and the magnitude of the dielectric loss is determined by the product of the frequency, the square root of the dielectric constant, and the dielectric loss tangent of the dielectric. Therefore, communication components used in high-frequency bands require materials with low dielectric constants and dielectric loss tangents to suppress dielectric loss. For example, Patent Document 1 proposes an adhesive composition for FPC-related products containing a styrene-based elastomer (A) with a specific structure, an alicyclic skeleton-containing resin (B), and an epoxy resin (C). Patent Document 2 proposes an adhesive composition for FPCs containing an acid-modified polyolefin (a), an oligophenylene ether (b) with a number-average molecular weight of 3,000 or less, and an epoxy resin (c).

[0004] International Publication No. WO2022 / 102505 US2021002523 A1

[0005] However, the cured products obtained by curing conventional adhesive compositions still do not have satisfactory electrical properties such as dielectric constant and dielectric loss tangent, and adhesive strength to copper wiring. Furthermore, the viscosity of the adhesive composition may increase during storage.

[0006] A primary object of the present invention is to provide a composition that can form a cured product that has an excellent balance between electrical properties and adhesive strength and that has excellent storage stability.

[0007] As a result of intensive research to solve the above problems, the present inventors have found that a composition containing a specific elastomer component and a specific radically polymerizable compound (B) can form a cured product that has an excellent balance between electrical properties and adhesive strength, and also has excellent storage stability, and have thus completed the present invention.

[0008] That is, the present invention provides a composition comprising a styrene-based elastomer (A) and a radically polymerizable compound (B), wherein the radically polymerizable compound (B) comprises a modified polyphenylene ether (B1) having an ethylenically unsaturated bond-containing group at a terminal, and an ethylenically unsaturated bond- and alkoxysilyl group-containing compound (B2), the content of the styrene-based elastomer (A) is 100 parts by mass or more and 1,000 parts by mass or less per 100 parts by mass of the modified polyphenylene ether (B1) having an ethylenically unsaturated bond-containing group at a terminal, and the content of the ethylenically unsaturated bond- and alkoxysilyl group-containing compound (B2) is 1.1 parts by mass or more and 10 parts by mass or less per 100 parts by mass of the styrene-based elastomer (A) and the radically polymerizable compound (B) combined.

[0009] In the present invention, the styrene-based elastomer (A) is preferably an elastomer having a structural unit derived from butadiene.

[0010] In the present invention, the ethylenically unsaturated bond-containing group of the modified polyphenylene ether (B1) having an ethylenically unsaturated bond-containing group at its terminal is preferably a vinylbenzyl group.

[0011] In the present invention, the ethylenically unsaturated bond and alkoxysilyl group-containing compound (B2) preferably contains a vinyl-based silane coupling agent.

[0012] The compositions of the present invention are preferably peroxide-free.

[0013] The present invention provides a cured product of the above-mentioned composition.

[0014] The present invention provides an adhesive comprising the above-mentioned composition.

[0015] The present invention has the effect of providing a composition that can form a cured product that has an excellent balance between electrical properties and adhesive strength and has excellent storage stability.

[0016] The present invention relates to a composition and a cured product thereof. The composition and cured product of the present invention will be described in detail below.

[0017] In this specification, the number of carbon atoms in a group refers to the number of carbon atoms in the group after substitution when a hydrogen atom in the group is substituted with a substituent. For example, when a hydrogen atom in an alkyl group having 1 to 20 carbon atoms is substituted, the term "1 to 20 carbon atoms" refers to the number of carbon atoms after the hydrogen atom is substituted, not the number of carbon atoms before the hydrogen atom is substituted. Furthermore, in this specification, the specification of the number of carbon atoms in a group in which a methylene group in a group with a specified number of carbon atoms is replaced with a divalent group refers to the number of carbon atoms in the group after the substitution.

[0018] In this specification, the term "solid content of the composition" refers to all components in the composition excluding the solvent.

[0019] A. Composition First, the composition of the present invention will be described. The composition of the present invention is a composition comprising a styrene-based elastomer (A) and a radically polymerizable compound (B), wherein the radically polymerizable compound (B) comprises a modified polyphenylene ether (B1) having an ethylenically unsaturated bond-containing group at a terminal, and an ethylenically unsaturated bond- and alkoxysilyl group-containing compound (B2), the content of the styrene-based elastomer (A) is 100 parts by mass or more and 1,000 parts by mass or less per 100 parts by mass of the modified polyphenylene ether (B1) having an ethylenically unsaturated bond-containing group at a terminal, and the content of the ethylenically unsaturated bond- and alkoxysilyl group-containing compound (B2) is 1.1 parts by mass or more and 10 parts by mass or less per 100 parts by mass of the combined total of the styrene-based elastomer (A) and the radically polymerizable compound (B).

[0020] Each component constituting the composition of the present invention will be described below.

[0021] A1. Styrenic Elastomer (A) The composition of the present invention contains a styrene-based elastomer (A). The styrene-based elastomer (A) may be a polymer containing a structural unit derived from a styrene-based compound (styrene-based structural unit) and a structural unit derived from a conjugated diene (conjugated diene structural unit). Examples of the styrene-based structural unit include those represented by the following general formula (A1-1):

[0022]

[0023] In general formula (A1-1), R ａ１ represents a hydrogen atom or an alkyl group having 1 to 5 carbon atoms; R ａ２ represents a halogen atom, a vinyl group, an amino group, or an alkyl group having 1 to 5 carbon atoms; n1 represents an integer of 0 to 5; * represents a bond.

[0024] The above R ａ１ and R ａ２The alkyl group having 1 to 5 carbon atoms represented by the formula (I) may be either a linear alkyl group or a branched alkyl group, and examples thereof include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, and an n-pentyl group.

[0025] The above R ａ２ Examples of the halogen atom represented by the formula (I) include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

[0026] When n1 is 2 or more, a plurality of R ａ２ may be the same, or may be partially or entirely different.

[0027] In the present invention, from the viewpoint of forming a cured product having an excellent balance between electrical properties and adhesive strength and providing a composition with excellent storage stability, R ａ１ and R ａ２ Preferably, both of the groups are alkyl groups having 1 to 3 carbon atoms, more preferably both of the groups are alkyl groups having 1 to 2 carbon atoms, and even more preferably both of the groups are methyl groups.

[0028] In general formula (A1-1) above, n1 is preferably an integer of 0 or more and 2 or less, more preferably 0 or 1, and even more preferably 0, from the viewpoint of being able to form a cured product that has an excellent balance between electrical properties and adhesive strength and resulting in a composition that has excellent storage stability.

[0029] From the viewpoint of forming a cured product having an excellent balance between electrical properties and adhesive strength and providing a composition with excellent storage stability, the content of the styrene-based constituent units is preferably from 3 to 80% by mass, more preferably from 20 to 70% by mass, and even more preferably from 30 to 65% by mass, of the total mass of the styrene-based elastomer (A).

[0030] The styrene-based structural unit in the styrene-based elastomer (A) may be composed of only one type of styrene-based structural unit represented by the general formula (A-1) above, or may be composed of two or more different types. When two or more types are contained, it is preferable that the total amount of the styrene-based structural units is within the above numerical range.

[0031] The styrene-based elastomer (A) contains a conjugated diene structural unit, which makes it easier to form a cured product with a low dielectric loss tangent and excellent electrical properties.

[0032] The conjugated diene structural unit is not particularly limited as long as it is formed by a polymerization reaction using a diolefin having a pair of conjugated double bonds. Examples of the conjugated diene structural unit constituting the styrene-based elastomer (A) include butadiene-derived structural units, pentadiene-derived structural units, and hexadiene-derived structural units, but in the present invention, butadiene-derived structural units are preferred. This is because they can form a cured product with an excellent balance between electrical properties and adhesive strength, and result in a composition with excellent storage stability.

[0033] The butadiene-derived structural unit is a structural unit formed by a polymerization reaction using a compound having a 1,3-butadiene structure. Examples of the compound having a 1,3-butadiene structure include 1,3-butadiene, 2-methyl-1,3-butadiene (isoprene), and 2,3-dimethyl-1,3-butadiene.

[0034] The pentadiene-derived structural unit refers to a structural unit formed by a polymerization reaction using a compound having a 1,3-pentadiene structure. Examples of the compound having a 1,3-pentadiene structure include 1,3-pentadiene (piperylene) and 2-methyl-1,3-pentadiene.

[0035] The hexadiene-derived structural unit refers to a structural unit obtained by a polymerization reaction using a compound having a 1,3-hexadiene structure, and examples of the compound having a 1,3-hexadiene structure include 1,3-hexadiene.

[0036] The conjugated diene structural unit in the styrene-based elastomer may be composed of only one type, or may be composed of two or more different types.

[0037] In the present invention, the mass ratio of the styrene structural units to the conjugated diene structural units in the styrene elastomer (A) is preferably in the range of styrene structural units / conjugated diene structural units = 3 / 97 to 80 / 20, more preferably 5 / 95 to 50 / 50, and even more preferably 8 / 92 to 20 / 80, because this allows for the formation of a cured product that has an excellent balance between electrical properties and adhesive strength, and results in a composition that has excellent storage stability.

[0038] The styrene-based elastomer (A) may be modified with a dicarboxylic acid compound (carboxy modification) or with an organic amine (amine modification). Examples of the modification method include a method of adding a radical generator to the styrene-based elastomer and the dicarboxylic acid compound or the organic amine and kneading them using an extruder, and a method of mixing the styrene-based elastomer and the dicarboxylic acid or the organic amine in a solvent that dissolves both of them.

[0039] Examples of the dicarboxylic acid compound used for carboxy modification include linear unsaturated dicarboxylic acid compounds and their anhydrides. The linear unsaturated dicarboxylic acid compound refers to a compound having a carbon-carbon unsaturated bond and two carboxy groups at both ends of the molecule, and examples thereof include fumaric acid, maleic acid, itaconic acid, citraconic acid, mesaconic acid, glutaconic acid, etc., and examples of the anhydrides thereof include fumaric acid anhydride, maleic acid anhydride, itaconic acid anhydride, citraconic acid anhydride, etc.

[0040] The organic amine represents a compound in which a hydrogen atom of ammonia is substituted with a hydrocarbon group or an aromatic atomic group, and examples thereof include alkylamines such as methylamine, ethylamine, propylamine, isopropylamine, n-butylamine, sec-butylamine, isobutylamine, tert-butylamine, and pentylamine; alkenylamines such as dodecenylamine, octadecenylamine, and docosenylamine; arylamines such as aniline, methylaniline, ethylaniline, p-isopropylaniline, and N-methylaniline; aralkylamines such as benzylamine, 1-phenylethylamine, and 2-phenylethylamine; cyclic alkylamines such as cyclohexylamine and dicyclohexylamine; and heterocyclic amines such as thienylamine and quinolylamine.

[0041] In the present invention, the styrene-based elastomer (A) is preferably unmodified, since this makes it easier to form a cured product having excellent adhesion to copper.

[0042] Examples of the styrene-based elastomer (A) include styrene-butadiene random copolymer (SBR), styrene-butadiene-styrene block copolymer (SBS), and styrene-isoprene-styrene block copolymer (SIS), but in the present invention, a hydrogenated product obtained by hydrogenating the double bonds of the conjugated diene structural units in the styrene-based elastomer (A) is preferred, because hydrogenation improves the heat resistance, weather resistance, etc. of the styrene-based elastomer (A).

[0043] Examples of hydrogenated products of the styrene-based elastomer (A) include hydrogenated styrene-butadiene random copolymer (HSBR), which is a hydrogenated product of SBR; styrene-ethylene-butylene-styrene block copolymer (SEBS), which is obtained by completely hydrogenating the carbon-carbon double bonds in the butadiene-derived structural units of SBS; styrene-butadiene-butylene-styrene block copolymer (SBBS), which is obtained by partially hydrogenating the carbon-carbon double bonds at the 1,2-bond sites in the butadiene-derived structural units; and styrene-ethylene-propylene-ethylene block copolymer (SEPS), which is a hydrogenated product of SIS. Note that "completely hydrogenated" typically means that the hydrogenation rate of the total carbon-carbon double bonds is 90% or more, but may also be 95% or more, 99% or more, or 100%. Furthermore, "partially hydrogenated" means, for example, that the hydrogenation rate of the total carbon-carbon double bonds is in the range of 60% to 85%.

[0044] Commercially available products of the styrene-based elastomer (A) include, for example, Tufprene A, Tufprene 125, Tufprene 126S, etc. (all manufactured by Asahi Kasei Corporation, SBS); SIBSTAR072T, SIBSTAR073T, SIBSTAR102T, SIBSTAR103T, etc. (all manufactured by Kaneka Corporation, SIS); DYNARON1320P, DYNARON1321P, DYNARON2324P, etc. (all manufactured by ENEOS Material Corporation, HSBR); DYNARON4600P, DYNARON6100P, DYNARON8600P, DYNARON8601, DYNARON8903P, DYNARON9901P, etc. (all manufactured by ENEOS Material Corporation, HSBR); (SEBS manufactured by ENEOS Material Corporation); Tuftec H1041, Tuftec 1043, Tuftec 1051, Tuftec H1052, Tuftec H1053, Tuftec H1062, Tuftec H1517, Tuftec H1221, Tuftec H1272, Tuftec N504, Tuftec P1083, Tuftec P1500, Tuftec P5051, Tuftec P2000, etc. (SEBS manufactured by Asahi Kasei Corporation); DYNARON 4630P, DYNARON 8300P, DYNARON 8630P, etc. (polar modified SEBS manufactured by ENEOS Material Corporation); Tuftec M1911, Tuftec M1913 Examples thereof include Tuftec M1943 (maleic anhydride-modified SEBS manufactured by Asahi Kasei Corporation); Tuftec MP10 (amine-modified SEBS manufactured by Asahi Kasei Corporation); and the like.

[0045] In the present invention, from the viewpoint of being able to form a cured product having an excellent balance between electrical properties and adhesive strength and of providing a composition having excellent storage stability, the styrene-based elastomer (A) is preferably selected from SBS, SEBS, SBBS, SIS, and SEPS, more preferably SEBS, SBBS, and SEPS, and even more preferably SEBS. Among SEBS, SEBS other than amine-modified SEBS is particularly preferred, and unmodified SEBS is most preferred.

[0046] The melt flow rate of the styrene-based elastomer (A) is not particularly limited, but from the viewpoint that the composition of the present invention can form a cured product having an excellent balance between electrical properties and adhesive strength and has excellent storage stability, the melt flow rate is preferably 0.1 g / 10 min or more and 50 g / 10 min or less, more preferably 1.0 g / 10 min or more and 20 g / 10 min or less, and even more preferably 2.0 g / 10 min or more and 10 g / 10 min or less, measured under measurement conditions in accordance with ISO 1133 at 230°C and a load of 2.16 kgf (21.2 N).

[0047] The specific gravity of the styrene-based elastomer (A) is not particularly limited, but from the viewpoint of enabling the composition of the present invention to form a cured product having an excellent balance between electrical properties and adhesive strength and having excellent storage stability, the specific gravity is preferably from 0.80 to 0.99, more preferably from 0.85 to 0.99, and even more preferably from 0.89 to 0.98, when measured under conditions in accordance with ISO 1183.

[0048] From the viewpoint that the composition of the present invention can form a cured product having an excellent balance between electrical properties and adhesive strength and has excellent storage stability, the content of the styrene-based elastomer (A) is preferably from 10 to 90 parts by mass, more preferably from 20 to 80 parts by mass, even more preferably from 30 to 70 parts by mass, and particularly preferably from 40 to 70 parts by mass, per 100 parts by mass of the solid content of the composition.

[0049] From the viewpoint that the composition of the present invention can form a cured product having an excellent balance between electrical properties and adhesive strength and has excellent storage stability, the content of the styrene-based elastomer (A) is preferably 10 parts by mass or more and 90 parts by mass or less, more preferably 20 parts by mass or more and 80 parts by mass or less, still more preferably 30 parts by mass or more and 70 parts by mass or less, and particularly preferably 40 parts by mass or more and 70 parts by mass or less, relative to 100 parts by mass of the total amount of the styrene-based elastomer (A) and the radically polymerizable compound (B) described below.

[0050] From the viewpoints of enabling the composition of the present invention to form a cured product having an excellent balance between electrical properties and adhesive strength and having excellent storage stability, the content of the styrene-based elastomer (A) is preferably from 51 to 500 parts by mass, more preferably from 70 to 400 parts by mass, even more preferably from 90 to 380 parts by mass, and particularly preferably from 115 to 360 parts by mass, relative to 100 parts by mass of the radically polymerizable compound (B) described below.

[0051] The content of the styrene-based elastomer (A) is from 100 parts by mass to 1,000 parts by mass per 100 parts by mass of the modified polyphenylene ether (B1) having an ethylenically unsaturated bond at its terminal, which will be described later. From the viewpoint that the composition of the present invention can form a cured product having an excellent balance between electrical properties and adhesive strength and has excellent storage stability, the content is more preferably from 100 parts by mass to 800 parts by mass, and even more preferably from 130 parts by mass to 500 parts by mass. The content is particularly preferably from 150 parts by mass to 300 parts by mass, since this facilitates the formation of a cured product having excellent electrical properties.

[0052] From the viewpoints of enabling the composition of the present invention to form a cured product having an excellent balance between electrical properties and adhesive strength and providing a composition with excellent storage stability, the content of the styrene-based elastomer (A) is preferably from 100 parts by mass to 10,000 parts by mass, more preferably from 500 parts by mass to 5,000 parts by mass, still more preferably from 800 parts by mass to 4,000 parts by mass, and particularly preferably from 900 parts by mass to 3,000 parts by mass, relative to 100 parts by mass of the ethylenically unsaturated bond- and alkoxysilyl group-containing compound (B2) described below.

[0053] A2. Radically Polymerizable Compound (B) The radically polymerizable compound (B) is a compound capable of radical polymerization and does not include the styrene-based elastomer (A). The composition of the present invention contains, as the radically polymerizable compound (B), a modified polyphenylene ether (B1) having an ethylenically unsaturated bond-containing group at its terminal and a compound (B2) containing an ethylenically unsaturated bond and an alkoxysilyl group.

[0054] (1) Modified Polyphenylene Ether (B1) Having an Ethylenically Unsaturated Bond-Containing Group at a Terminal The modified polyphenylene ether (B1) having an ethylenically unsaturated bond-containing group at a terminal (hereinafter sometimes referred to as "modified polyphenylene ether (B1)") is a polyphenylene ether having an ethylenically unsaturated bond-containing group at a molecular terminal, and from the viewpoint that the composition of the present invention can form a cured product having an excellent balance of electrical properties and adhesive strength and becomes a composition having excellent storage stability, it is preferably a polyphenylene ether having an ethylenically unsaturated bond-containing group at both molecular terminals. Note that, in this specification, the term "ethylenically unsaturated bond-containing group" refers to a substituent containing a carbon-carbon double bond capable of undergoing a polymerization reaction, and does not include a substituent in which the only carbon-carbon double bond is an aromatic ring double bond.

[0055] The modified polyphenylene ether (B1) may, for example, be a polymer having a phenylene ether bond represented by the following general formula (B1-1) as a constituent unit.

[0056]

[0057] In general formula (B1-1), R ｂ１ represents a halogen atom or an alkyl group having 1 to 5 carbon atoms; n2 represents an integer of 0 to 4; and * represents a bond.

[0058] R in the above general formula (B1-1) ｂ１ The halogen atom or the alkyl group having 1 to 5 carbon atoms represented by the formula (A1-1) is R ａ２ or an alkyl group having 1 to 5 carbon atoms.

[0059] When n2 is an integer of 2 or more, a plurality of R ｂ１ may be the same, or may be partially or entirely different.

[0060] In the present invention, the modified polyphenylene ether (B1) is preferably a polymer containing a structural unit represented by the following general formula (B1-2), because the composition of the present invention can form a cured product having an excellent balance between electrical properties and adhesive strength, and is a composition with excellent storage stability.

[0061]

[0062] In formula (B1-2), * represents a bond.

[0063] Examples of the ethylenically unsaturated bond-containing group include a vinyl group, an allyl group, a vinyl ether group, a vinyl ester group, a 1-methylallyl group, an isopropenyl group, a 2-butenyl group, a 3-butenyl group, a styryl group, a vinylbenzyl group, an acryloyl group, a methacryloyl group, a 1-acryloylmethyl group, a 1-methacryloylmethyl group, a 2-acryloylethyl group, a 2-methacryloylethyl group, a 3-acryloylpropyl group, and a 3-methacryloylpropyl group.

[0064] From the viewpoint that the composition of the present invention can form a cured product having an excellent balance between electrical properties and adhesive strength and has excellent storage stability, the ethylenically unsaturated bond-containing group is preferably a group selected from a styryl group, a vinylbenzyl group, an acryloyl group, and a methacryloyl group, and more preferably a group selected from a vinylbenzyl group, an acryloyl group, and a methacryloyl group.

[0065] In the present invention, it is more preferable that the terminal ethylenically unsaturated bond-containing group of the modified polyphenylene ether (B1) is a vinylbenzyl group, because the composition of the present invention can form a cured product having an excellent balance between electrical properties and adhesive strength, and the composition has excellent storage stability.

[0066] From the viewpoint that the composition of the present invention can form a cured product having an excellent balance between electrical properties and adhesive strength and has excellent storage stability, the modified polyphenylene ether (B1) preferably contains a polymer represented by the following general formula (B1-3):

[0067]

[0068] In general formula (B1-3), R ｂ１ and n2 are the same as the respective symbols in the general formula (B1-1) above, R ｂ２ and R ｂ３ each independently represents a halogen atom or an alkyl group having 1 to 5 carbon atoms; n3 and n4 each independently represents an integer of 0 to 4; s and t each independently represents an integer of 0 to 20, and the sum of s and t is an integer of 1 to 30. X ｂ１ represents an alkylene group having from 1 to 5 carbon atoms, an alkylidene group having from 2 to 5 carbon atoms, an ether group, a sulfide group, a sulfonyl group, a carbonyloxy group, a keto group, or a single bond; Y ｂ１ and Y ｂ２ each independently represents an ethylenically unsaturated bond-containing group.

[0069] R in the above general formula (B1-3) ｂ２ and R ｂ３ The halogen atom or the alkyl group having 1 to 5 carbon atoms represented by the formula (A1-1) is R ａ２ or an alkyl group having 1 to 5 carbon atoms.

[0070] In the present invention, from the viewpoint that the composition of the present invention can form a cured product having an excellent balance between electrical properties and adhesive strength and has excellent storage stability, R ｂ２ and R ｂ３ is preferably an alkyl group having 1 to 5 carbon atoms, more preferably an alkyl group having 1 to 3 carbon atoms, further preferably a methyl group or an ethyl group, and particularly preferably a methyl group.

[0071] In the general formula (B1-3), n3 and n4 each represent an integer of 0 to 4, and from the viewpoint of facilitating the formation of a cured product of the composition of the present invention that is excellent in electrical properties and adhesive strength, an integer of 0 to 3 is more preferred, and 2 or 3 is even more preferred. When n3 or n4 is an integer of 2 or greater, multiple R ｂ２ R ｂ３ They may be the same or may be partially or entirely different.

[0072] s and t each represent an integer of 0 or more and 20 or less, and from the viewpoint that the composition of the present invention can form a cured product having an excellent balance between electrical properties and adhesive strength and has excellent storage stability, an integer of 1 or more and 20 or less is more preferable, an integer of 2 or more and 15 or less is even more preferable, and an integer of 3 or more and 10 or less is particularly preferable. When s or t is an integer of 2 or more, a plurality of R ｂ１ They may be the same, or some or all of them may be different.

[0073] X in the above general formula (B1-3) ｂ１ Examples of the alkylene group having 1 to 5 carbon atoms represented by the formula (I) include a methylene group, a 1,2-dimethylene group, a 1,3-trimethylene group, a dimethylmethylene group, a 1,4-tetramethylene group, and a 1,5-pentamethylene group.

[0074] X ｂ１ Examples of the alkylidene group having 2 to 5 carbon atoms represented by the formula (I) include an ethylidene group, a propylidene group, an isopropylidene group, a butylidene group, an isobutylidene group, a pentylidene group, and an isopentylidene group.

[0075] From the viewpoint that the composition of the present invention can form a cured product having an excellent balance between electrical properties and adhesive strength and has excellent storage stability, ｂ１ is more preferably a single bond or an alkylene group having 1 to 5 carbon atoms, further preferably a single bond or a dimethylmethylene group, and particularly preferably a single bond.

[0076] The method for synthesizing the modified polyphenylene ether (B1) is not particularly limited, and known methods for synthesizing and modifying modified polyphenylene ethers can be applied.

[0077] Commercially available modified polyphenylene ethers (B1) include, for example, OPE-2St-1200 and OPE-2st-2200 (vinyl-modified polyphenylene ethers manufactured by Mitsubishi Gas Chemical Co., Inc.); and NORYL SA9000 and NORYL SA9000-111 (methacrylic-modified polyphenylene ethers manufactured by SHPP Japan LLC).

[0078] The number average molecular weight of the modified polyphenylene ether (B1) is not particularly limited, but from the viewpoint that the composition of the present invention can form a cured product having an excellent balance between electrical properties and adhesive strength and has excellent storage stability, it is preferably from 500 to 7,000, more preferably from 800 to 5,000, even more preferably from 1,000 to 3,000, and particularly preferably from 1,100 to 2,500. In this specification, the number average molecular weight is a value calculated from a calibration curve using standard polystyrene by gel permeation chromatography (GPC).

[0079] In the composition of the present invention, the radically polymerizable compound (B) may contain only one type of the modified polyphenylene ether (B1) or may contain two or more types in combination.

[0080] The content of the modified polyphenylene ether (B1) is preferably from 1 to 49 parts by mass, more preferably from 2 to 30 parts by mass, and even more preferably from 3 to 20 parts by mass, per 100 parts by mass of the composition, from the viewpoint that the composition of the present invention can form a cured product having an excellent balance between electrical properties and adhesive strength and that the composition has excellent storage stability. An amount of from 4 to 10 parts by mass is particularly preferred, as it allows the formation of a cured product having excellent adhesive strength.

[0081] From the viewpoint that the composition of the present invention can form a cured product having an excellent balance between electrical properties and adhesive strength and has excellent storage stability, the content of the modified polyphenylene ether (B1) is preferably 1 part by mass or more and 49 parts by mass or less, more preferably 10 parts by mass or more and 45 parts by mass or less, and even more preferably 15 parts by mass or more and 40 parts by mass or less, per 100 parts by mass of the solid content of the composition.

[0082] From the viewpoint that the composition of the present invention can form a cured product having an excellent balance between electrical properties and adhesive strength and has excellent storage stability, the content of the modified polyphenylene ether (B1) is preferably from 1 part by mass to 49 parts by mass, more preferably from 10 parts by mass to 45 parts by mass, and even more preferably from 15 parts by mass to 40 parts by mass, per 100 parts by mass of the styrene-based elastomer (A) and the radical-polymerizable compound (B).

[0083] From the viewpoint that the composition of the present invention can form a cured product having an excellent balance between electrical properties and adhesive strength and has excellent storage stability, the content of the modified polyphenylene ether (B1) is preferably from 50 parts by mass to 95 parts by mass, more preferably from 60 parts by mass to 93 parts by mass, even more preferably from 70 parts by mass to 90 parts by mass, and particularly preferably from 80 parts by mass to 90 parts by mass, per 100 parts by mass of the radical polymerizable compound (B).

[0084] From the viewpoint that the composition of the present invention can form a cured product having an excellent balance between electrical properties and adhesive strength and has excellent storage stability, the content of the modified polyphenylene ether (B1) is preferably from 100 parts by mass to 5,000 parts by mass, more preferably from 200 parts by mass to 3,000 parts by mass, even more preferably from 400 parts by mass to 2,000 parts by mass, and particularly preferably from 500 parts by mass to 1,000 parts by mass, relative to 100 parts by mass of the ethylenically unsaturated bond- and alkoxysilyl group-containing compound (B2) described below.

[0085] From the viewpoint that the composition of the present invention can form a cured product having an excellent balance between electrical properties and adhesive strength and has excellent storage stability, the content of the modified polyphenylene ether (B1) is 100 parts by mass or less, preferably 10 parts by mass or more and 100 parts by mass or less, more preferably 12 parts by mass or more and 100 parts by mass or less, even more preferably 20 parts by mass or more and 77 parts by mass or less, and particularly preferably 33 parts by mass or more and 89 parts by mass or less, relative to 100 parts by mass of the styrene-based elastomer (A).

[0086] (2) Ethylenically unsaturated bond- and alkoxysilyl group-containing compound (B2) The ethylenically unsaturated bond- and alkoxysilyl group-containing compound (B2) may be a compound having an ethylenically unsaturated bond-containing group at the molecular terminal and containing an alkoxysilyl group. The "ethylenically unsaturated bond-containing group" refers to the same as that described in the section "(1) Modified polyphenylene ether (B1) having an ethylenically unsaturated bond-containing group at its terminal." The ethylenically unsaturated bond- and alkoxysilyl group-containing compound (B2) does not include the modified polyphenylene ether (B1). The ethylenically unsaturated bond- and alkoxysilyl group-containing compound (B2) may have multiple ethylenically unsaturated bond-containing groups, but is preferably a compound having one ethylenically unsaturated bond-containing group at the molecular terminal and an alkoxysilyl group at the other terminal. This is because the composition of the present invention can form a cured product having an excellent balance of electrical properties and adhesive strength, and is a composition with excellent storage stability.

[0087] Examples of the alkoxysilyl group include groups represented by the following general formula (B2-1).

[0088]

[0089] In the above general formula (B2-1), R ｂ４ and R ｂ５ each independently represents an alkyl group having 1 to 5 carbon atoms, n5 represents an integer of 0 to 2, n6 represents an integer of 1 to 3, provided that the sum of n5 and n6 is 3, and * represents a bond.

[0090] R in the above general formula (B2-1) ｂ４ and Ｒｂ５ The alkyl group having 1 to 5 carbon atoms represented by the formula (A1-1) is R ａ１ The alkyl group may be the same as the alkyl group having 1 to 5 carbon atoms represented by the following formula:

[0091] When n5 is 2, a plurality of R ｂ４ When n6 is an integer of 2 or more, a plurality of R ｂ５may be the same, or may be partially or entirely different.

[0092] From the viewpoint that the composition of the present invention can form a cured product having an excellent balance between electrical properties and adhesive strength and has excellent storage stability, it is preferable that n5 is 0 and n6 is 3.

[0093] The method for synthesizing the ethylenically unsaturated bond- and alkoxysilyl group-containing compound (B2) is not particularly limited, and any known method for synthesizing an alkoxysilyl group-containing compound can be applied.

[0094] Examples of the ethylenically unsaturated bond and alkoxysilyl group-containing compound (B2) include vinyl silane coupling agents. The vinyl silane coupling agents are compounds having a vinyl group and a group represented by the general formula (B2-1). Compounds having a group represented by the general formula (B2-1) also include compounds having a functional group containing a vinyl group in the structure (e.g., an acryloyl group, a methacryloyl group, a styryl group, etc.).

[0095] Commercially available examples of the vinyl silane coupling agent include KBM-1003 (vinyltrimethoxysilane), KBE-1003 (vinyltriethoxysilane), KBM-1403 (p-styryltrimethoxysilane), KBM-502 (3-methacryloxypropylmethyldimethoxysilane), KBM-503 (3-methacryloxypropyltrimethoxysilane), KBE-502 (3-methacryloxypropylmethyldiethoxysilane), KBE-503 (3-methacryloxypropyltriethoxysilane), and KBM-5103 (3-acryloxypropyltrimethoxysilane) (all silane coupling agents manufactured by Shin-Etsu Chemical Co., Ltd.).

[0096] In the present invention, from the viewpoint of being able to form a cured product having an excellent balance between electrical properties and adhesive strength, the ethylenically unsaturated bond and alkoxysilyl group-containing compound (B2) preferably contains a vinyl silane coupling agent, and among the vinyl silane coupling agents, it is more preferable to contain a vinyl silane coupling agent having an acryloyl group or a methacryloyl group, and it is even more preferable to contain a vinyl silane coupling agent having an acryloyl group.

[0097] In the present invention, the radical polymerizable compound (B) may contain only one of the ethylenically unsaturated bond- and alkoxysilyl group-containing compounds (B2), or may contain two or more of them in combination. However, in the present invention, from the viewpoint of being able to form a cured product having an excellent balance between electrical properties and adhesive strength, it is more preferable that the radical polymerizable compound (B) contains two or more vinyl silane coupling agents in combination, and among these, it is even more preferable that the radical polymerizable compound (B) contains a combination of a vinyl silane coupling agent having an acryloyl group and a vinyl silane coupling agent having a vinyl group.

[0098] In the composition of the present invention, the content of the ethylenically unsaturated bond- and alkoxysilyl group-containing compound (B2) is from 1.1 to 10 parts by mass, more preferably from 2 to 9 parts by mass, and even more preferably from 3 to 8 parts by mass, per 100 parts by mass of the total of the styrene-based elastomer (A) and the radically polymerizable compound (B), because the composition of the present invention can form a cured product having an excellent balance between electrical properties and adhesive strength and has excellent storage stability.

[0099] From the viewpoints of enabling the composition of the present invention to form a cured product having an excellent balance between electrical properties and adhesive strength and of providing a composition with excellent storage stability, the content of the ethylenically unsaturated bond- and alkoxysilyl group-containing compound (B2) is preferably from 0.1 to 7 parts by mass, more preferably from 0.2 to 5 parts by mass, and even more preferably from 0.3 to 3 parts by mass, per 100 parts by mass of the composition.

[0100] From the viewpoint that the composition of the present invention can form a cured product having an excellent balance between electrical properties and adhesive strength and has excellent storage stability, the content of the ethylenically unsaturated bond- and alkoxysilyl group-containing compound (B2) is preferably from 0.1 parts by mass to 10 parts by mass, more preferably from 1.1 parts by mass to 9 parts by mass, even more preferably from 2 parts by mass to 8 parts by mass, and particularly preferably from 3 parts by mass to 7.5 parts by mass, per 100 parts by mass of the solid content of the composition.

[0101] From the viewpoint that the composition of the present invention can form a cured product having an excellent balance between electrical properties and adhesive strength and has excellent storage stability, the content of the ethylenically unsaturated bond- and alkoxysilyl group-containing compound (B2) is preferably 1 part by mass or more and 50 parts by mass or less, more preferably 5 parts by mass or more and 30 parts by mass or less, and even more preferably 7 parts by mass or more and 20 parts by mass or less, relative to 100 parts by mass of the radically polymerizable compound (B).

[0102] From the viewpoints of enabling the composition of the present invention to form a cured product having an excellent balance between electrical properties and adhesive strength and providing a composition with excellent storage stability, the content of the ethylenically unsaturated bond- and alkoxysilyl group-containing compound (B2) is preferably from 0.1 parts by mass to 20 parts by mass, more preferably from 1 part by mass to 15 parts by mass, and even more preferably from 4 parts by mass to 13 parts by mass, relative to 100 parts by mass of the styrene-based elastomer (A).

[0103] (3) Other radical polymerizable compounds (B3) The composition of the present invention may contain other radical polymerizable compounds (B3) as the radical polymerizable component (B). The other radical polymerizable compounds (B3) are compounds having radical polymerization reactivity, excluding the modified polyphenylene ether (B1) and the ethylenically unsaturated bond- and alkoxysilyl group-containing compound (B2).

[0104] A3. Other Component (C) The composition of the present invention contains the styrene-based elastomer (A) and the radically polymerizable compound (B), and may further contain other component (C) as needed.

[0105] Examples of the other component (C) include various additives such as resins other than the styrene-based elastomer (A) and the radically polymerizable compound (B), solvents, radical polymerization initiators such as peroxides, curing accelerators, sensitizers, leveling agents, fillers such as inorganic fillers and organic fillers, colorants such as pigments and dyes, antifoaming agents, thickeners, thixotropic agents, surfactants, dispersants, flame retardants, plasticizers, antioxidants, stabilizers, polymerization inhibitors, ultraviolet absorbers, antistatic agents, flow regulators, and adhesion promoters. The other components may be used alone or in combination of two or more.

[0106] (1) Solvent The composition of the present invention may contain a solvent as needed. Examples of the solvent include those that are liquid at room temperature (25°C) and atmospheric pressure and are capable of dispersing or dissolving the components of the composition of the present invention. However, the styrene elastomer (A) and the radically polymerizable compound (B) are not considered solvents even if they are liquid at room temperature and atmospheric pressure. Examples of the solvent include water and organic solvents, but organic solvents are preferred because they make it easier to disperse the composition of the present invention.

[0107] Examples of the organic solvent include ketones such as methyl ethyl ketone, methyl amyl ketone, diethyl ketone, acetone, methyl isopropyl ketone, methyl isobutyl ketone, cyclohexanone, and 2-heptanone; ether-based solvents such as ethyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane, and dipropylene glycol dimethyl ether; ester-based solvents such as methyl acetate, ethyl acetate, n-propyl acetate, isopropyl acetate, n-butyl acetate, cyclohexyl acetate, ethyl lactate, dimethyl succinate, and Texanol; cellosolve-based solvents such as ethylene glycol monomethyl ether and ethylene glycol monoethyl ether; alcohol-based solvents such as methanol, ethanol, iso- or n-propanol, iso- or n-butanol, amyl alcohol, and diacetone alcohol; ethylene glycol monomethyl acetate, ethylene glycol monoethyl acetate, propylene glycol ether-1-monomethyl ether-2-acetate (PGMEA), Ether ester solvents such as dipropylene glycol monomethyl ether acetate, 3-methoxybutyl acetate, ethoxyethyl propionate, 1-tert-butoxy-2-propanol, and cyclohexanol acetate; aromatic solvents such as benzene, toluene, and xylene; aliphatic hydrocarbon solvents such as hexane, heptane, octane, and cyclohexane; terpene hydrocarbon oils such as turpentine oil, D-limonene, and pinene; mineral spirits, Swazol #310 (Cosmo Matsuyama Oil Co., Ltd.) and Solvesso #100 (Exxon Chemical Co., Ltd.); halogenated aliphatic hydrocarbon solvents such as carbon tetrachloride, chloroform, trichloroethylene, methylene chloride, and 1,2-dichloroethane; halogenated aromatic hydrocarbon solvents such as chlorobenzene; carbitol-based solvents, aniline, triethylamine, pyridine, acetic acid, acetonitrile, carbon disulfide, N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, dimethyl sulfoxide, and water. In the present invention, the above-mentioned solvents may be used alone or in combination as a mixed solvent of two or more thereof.

[0108] In the present invention, the solvent preferably contains a ketone, an alcohol-based solvent, an ether ester-based solvent, or an aromatic solvent, and more preferably contains a ketone or an aromatic solvent, because the cured product of the composition of the present invention will have excellent electrical properties and adhesive strength.

[0109] When the composition of the present invention contains the above-mentioned solvent, the content of the solvent may be such that the cured product of the composition of the present invention has excellent electrical properties and adhesive strength. For example, the content of the solvent is preferably 1 part by mass or more and 1,000 parts by mass or less, more preferably 10 parts by mass or more and 800 parts by mass or less, even more preferably 100 parts by mass or more and 600 parts by mass or less, and particularly preferably 250 parts by mass or more and 500 parts by mass or less, relative to 100 parts by mass of the solid content of the composition.

[0110] (2) Peroxides Examples of the peroxides include peroxides well known as thermal radical polymerization initiators, but the composition of the present invention preferably does not contain any peroxides, because this can prevent the viscosity of the composition from increasing during long-term storage.

[0111] A4. Composition The method for producing the composition is not particularly limited as long as it can uniformly mix the components, and examples thereof include a method in which the styrene elastomer (A) and the radical polymerizable compound (B) are added to the solvent and mixed. Regarding the mixing method, a method using a known mixing device can be used, and examples thereof include a method using a three-roll mill, a sand mill, a ball mill, etc.

[0112] The uses of the composition of the present invention are not particularly limited as long as the cured product of the composition is required to have a balance between electrical properties and adhesive strength. Examples of uses of the composition of the present invention include adhesives, resist materials for printed wiring boards, various coating fields such as resist inks, pigment resist inks for car filters, semiconductor encapsulants, inks, plastic paints, paper printing, film coatings, glass coatings, shatterproof paints, and furniture paints, FRP, linings, and further in the electronics field, display media such as insulating varnishes, insulating sheets, laminates, plasma display panels, and display elements, optical anisotropics such as retardation plates, polarizing plates, light polarizing prisms, and various optical filters, insulating materials, structural materials, and optical waveguide clads.

[0113] The composition of the present invention is preferably used as an adhesive, more preferably for bonding conductive materials to insulating materials or insulating materials to each other, because the cured product of the composition of the present invention can effectively exhibit the effects of excellent electrical properties and adhesive strength.

[0114] When the composition of the present invention is used as an adhesive, the insulating material to be adhered can be the material used for the insulating substrate of a circuit board.The insulating material can be, for example, a material having a dielectric loss tangent (10 GHz) of 0.01 or less, for example, organic insulating materials such as polyimide (PI), polyethylene terephthalate (PET), polyethylene naphthalate (PEN), fluororesin (PTFE, etc.), polyphenylene ether and liquid crystal polymer (LCP), inorganic oxide materials such as glass, etc.

[0115] Examples of combinations of conductive materials and insulating materials include combinations of conductive materials such as metal materials or carbon materials with the above-mentioned insulating materials, such as a laminate formed by bonding a liquid crystal polymer film and copper foil.

[0116] Examples of combinations of insulating materials include combinations of the above insulating materials with the above insulating materials, such as a laminate formed by bonding together a film of liquid crystal polymer and another film of liquid crystal polymer, and combinations of an organic insulating material such as a liquid crystal polymer with an inorganic oxide material such as glass.

[0117] B. Cured Product Next, the cured product of the present invention will be described. The cured product of the present invention is a cured product of the composition of the present invention. According to the present invention, since the above-mentioned composition is used, a cured product having an excellent balance between electrical properties and adhesive strength can be provided. Note that the composition of the present invention is the same as that described in the above section "A. Composition," and therefore a description thereof will be omitted here.

[0118] The uses of the cured product of the present invention may be the same as those described in the section "A. Composition" above.

[0119] The method for producing the cured product of the present invention may be any method for curing the composition of the present invention, including a curing step of curing radically polymerizable compounds (B) together.

[0120] (1) Curing Step This step is a step of curing the radical polymerizable compounds (B) in the composition. The method for curing the radical polymerizable compounds (B) may be any well-known method utilizing a radical polymerization reaction, and examples thereof include a method of performing a heat treatment.

[0121] The heating temperature in the heat treatment may be any temperature that allows the composition to be stably cured, and may be from 50° C. to 300° C., more preferably from 100° C. to 250° C., and even more preferably from 150° C. to 230° C. The heating time may be from 1 minute to 5 hours, preferably from 3 minutes to 3 hours, and even more preferably from 5 minutes to 1 hour. This is because a cured product having excellent electrical properties and adhesive strength can be easily formed from the composition.

[0122] When the composition does not contain a peroxide (particularly, a peroxide as a thermal radical polymerization initiator), the method for curing the composition of the present invention is preferably the heat treatment, because the heat treatment is thought to cause decomposition of the radically polymerizable compound (B) to generate radicals, which act as starting points for the polymerization reaction (radical polymerization) of the composition of the present invention.

[0123] (2) Other Steps The method for producing a cured product may include other steps as needed, such as a pre-baking step in which the composition is heat-treated to remove the solvent in the composition before the curing step, and a step in which a coating film of the composition of the present invention is formed before the curing step.

[0124] The heating conditions in the pre-baking step may be any conditions that can remove the solvent in the composition, and may be, for example, 70° C. to 150° C. for 30 to 300 seconds.

[0125] In the step of forming a coating film, the composition can be applied by any known method such as using a spin coater, a roll coater, a bar coater, a die coater, a curtain coater, various types of printing, dipping, etc. Such a coating film can be formed on a substrate.

[0126] The substrate can be appropriately selected depending on the application of the cured product, and examples thereof include the objects on which the cured product is formed, as described above in the section "A. Composition." After being formed on a substrate, the cured product of the present invention may be peeled from the substrate and used, or may be transferred from the substrate to another adherend and used.

[0127] The present invention is not limited to the above-described embodiments. The above-described embodiments are merely examples, and any configuration that is substantially identical to the technical idea described in the claims of the present invention and that provides similar effects is included within the technical scope of the present invention.

[0128] The present invention will be explained in more detail below by showing specific examples of the composition of the present invention, but the present invention is not limited to these examples.

[0129] [Examples 1 to 13 and Comparative Examples 1 to 8] Compositions were obtained by blending the components according to the formulations shown in Table 1 below. The following materials were used for each component. The blending amounts in the table represent parts by mass of each component.

[0130] Styrene-based elastomers (A) A-1: ​​Dynaron 9901P (SEBS manufactured by ENEOS Materials Corporation, specific gravity 0.97, MFR 3.3 g / 10 min, styrene content 53% by mass) A-2: Tuftec H1043 (SEBS manufactured by Asahi Kasei Corporation, specific gravity 0.97, MFR 2.0 g / 10 min, styrene content 67% by mass) A-3: Tuftec MP10 (amine-modified SEBS manufactured by Asahi Kasei Corporation, specific gravity 0.91, MFR 4.0 g / 10 min, styrene content 30% by mass)

[0131] Modified polyphenylene ether (B1) having an ethylenically unsaturated bond at its terminal B1-1: OPE-2St-2200 (modified polyphenylene ether manufactured by Mitsubishi Gas Chemical Co., Inc.; the blending amount shown in the table indicates the content of solids (polymer having the following structure and a number average molecular weight of 2,200).) B1-2: OPE-2St-1200 (modified polyphenylene ether manufactured by Mitsubishi Gas Chemical Co., Inc.; the blending amount shown in the table indicates the content of solids (polymer having the following structure and a number average molecular weight of 1,200).) B1-3: NORYL SA-9000 (modified polyphenylene ether manufactured by Sabic; polymer having the following structure and a number average molecular weight of 1,700)

[0132] s1 and t1, and s2 and t2 each independently represent a number that results in a predetermined number average molecular weight.

[0133] Ethylenically unsaturated bond and alkoxysilyl group-containing compounds (B2) B2-1: KBM-5103 (manufactured by Shin-Etsu Chemical Co., Ltd., vinyl-based silane coupling agent having an acryloyl group, molecular weight 234.32) B2-2: KBM-503 (manufactured by Shin-Etsu Chemical Co., Ltd., vinyl-based silane coupling agent having a methacryloyl group, molecular weight 248.4) B2-3: KBM-1003 (manufactured by Shin-Etsu Chemical Co., Ltd., vinyl-based silane coupling agent having a vinyl group, molecular weight 148.23)

[0134]

[0135] Other radically polymerizable compounds (B3) B3-1: NK Ester DCP (manufactured by Shin-Nakamura Chemical Co., Ltd., tricyclodecane dimethanol dimethacrylate, molecular weight 332.4) B3-2: triallyl isocyanurate (TAIC, molecular weight 249.27) B3-3: NK Ester A-9300 (manufactured by Shin-Nakamura Chemical Co., Ltd., tris(2-acryloxyethyl) isocyanurate, molecular weight 375.38) B3-4: OGSOL EA-0200 (manufactured by Osaka Gas Chemicals Co., Ltd., fluorene-based epoxy resin, epoxy equivalent 290)

[0136] Other Components (C) C-1: KBM-803 (manufactured by Shin-Etsu Chemical Co., Ltd., silane coupling agent having a thiol structure, 3-mercaptopropyltrimethoxysilane, molecular weight 196.4) C-2: Perbutyl E (manufactured by NOF Corporation, thermal radical polymerization initiator, peroxide) C-3: MEK (solvent) C-4: toluene (solvent)

[0137] [Evaluation Examples] (1) Electrical Properties 2 g of each composition of the Examples and Comparative Examples was placed in a release-treated screw tube (20 cc) and heated at 60°C for 12 hours to remove the solvent, yielding a resin film. The resin film had a thickness of 500 μm. The resulting resin film was heat-treated at 180°C for 60 minutes to prepare an evaluation sample. The relative permittivity and dielectric loss tangent of the evaluation sample were measured at a frequency of 10 GHz using a coaxial resonator manufactured by AET Corporation, and the evaluation was performed according to the following criteria. The results are shown in Table 1.

[0138] <Evaluation Criteria> (Dielectric Constant) ++: Less than 2.0 +: 2.0 or more and less than 2.5 -: 2.5 or more It can be determined that the smaller the dielectric constant, the more excellent the electrical properties.

[0139] (Dielectric loss tangent) ++: Less than 0.002 +: 0.002 or more and less than 0.003 -: 0.003 or more It can be determined that the smaller the dielectric loss tangent, the more excellent the electrical properties.

[0140] (2) Adhesion Strength Each composition of the examples and comparative examples was applied to a copper foil (manufactured by Fukuda Metal Foil Industry Co., Ltd., "CF-T49A-DS-HD2-12") as a first substrate by a bar coater method so that the thickness after curing (thickness of the adhesive layer) was 25 μm, and then heated at 80 ° C. for 3 minutes to remove the solvent. Next, a copper foil (manufactured by Fukuda Metal Foil Industry Co., Ltd., "CF-T49A-DS-HD2-12") as a second substrate was superimposed on the dried coating film, and then a lamination process was performed using a vacuum pressure laminator (manufactured by Nikko Materials Co., Ltd., "V130") (after reducing the pressure to 2.0 hPa or less over 30 seconds, the laminate was then pressed at 100 ° C. and 0.5 MPa for 30 seconds), and then heat-treated at 200 ° C. for 60 minutes while applying 0.01 MPa to obtain an evaluation sample. Using this evaluation sample, a 90-degree peel test was performed in accordance with ISO standard 29862. A benchtop load measuring instrument FTN1-13A (manufactured by Aiko Engineering Co., Ltd.) was used as the measuring device, and the first substrate was pulled in a 90-degree direction under conditions of a measurement temperature of 25°C and a pulling speed of 50 mm / min, and the maximum strength when the first substrate peeled from the second substrate was evaluated as the peel strength (N / 25 mm). The results are shown in Table 1.

[0141] <Evaluation criteria> +++: 30N / 25mm or more. ++: 20N / 25mm or more and less than 30N / 25mm. +: 10N / 25mm or more and less than 20N / 25mm. -: Less than 10N / 25mm.

[0142] (3) Tg (°C) of Cured Product Each composition of the Examples and Comparative Examples was applied to a release polyethylene terephthalate (PET) film using a bar coater so that the thickness of the cured product was 30 μm, then dried at 80°C for 2 minutes and further heated at 200°C for 1 hour to cure the coating and obtain a cured product. The cured product was removed and cut into a size of 5 mm x 20 mm, and Tg was measured using a viscoelasticity measuring device (DMA7100) manufactured by Hitachi High-Tech Science Corporation and evaluated according to the following criteria. The results are shown in Table 1.

[0143] <Evaluation criteria> ++: 180°C or higher. +: 150°C or higher but less than 180°C. -: Less than 150°C.

[0144] (4) Evaluation of Solubility The appearance of each composition of the Examples and Comparative Examples was visually observed and evaluated. The results are shown in Table 1.

[0145] <Evaluation criteria> ++: The composition is a transparent liquid solution. +: The composition is a jelly-like solution. -: The composition contains insoluble matter.

[0146] (5) Liquid Stability The viscosity of each composition of the Examples and Comparative Examples immediately after production and after standing at 23°C for one month was measured using a viscometer (a cone-plate viscometer (TVE-22H manufactured by Toki Sangyo Co., Ltd.)) in an atmosphere of 25°C, and evaluated according to the following criteria. The results are shown in Table 1.

[0147] <Evaluation criteria> ++: The rate of change in viscosity after standing for one month relative to the viscosity immediately after production is less than 5%. +: The rate of change in viscosity after standing for one month relative to the viscosity immediately after production is 5% or more but less than 10%. -: The rate of change in viscosity after standing for one month relative to the viscosity immediately after production is 10% or more.

[0148] (6) Coating Stability Each composition of the Examples and Comparative Examples was applied to a PET film substrate using a bar coater to form a coating film with a thickness of 20 μm. After the coating film was left to stand at 23° C. for one month, the solubility of the coating film in toluene was visually observed and evaluated according to the following criteria. The results are shown in Table 1.

[0149] <Evaluation criteria> +: Dissolved in toluene. -: Dissolved in toluene but precipitate formed, or insoluble in toluene.

[0150]

[0151] From the above results, it was confirmed that the composition of the present invention can form a cured product that has an excellent balance between electrical properties and adhesive strength, and has excellent storage stability.

Claims

1. A composition comprising a styrene-based elastomer (A) and a radically polymerizable compound (B), wherein the radically polymerizable compound (B) comprises a modified polyphenylene ether (B1) having an ethylenically unsaturated bond-containing group at a terminal, and an ethylenically unsaturated bond- and alkoxysilyl group-containing compound (B2), the content of the styrene-based elastomer (A) is 100 parts by mass or more and 1,000 parts by mass or less per 100 parts by mass of the modified polyphenylene ether (B1) having an ethylenically unsaturated bond at a terminal, and the content of the ethylenically unsaturated bond- and alkoxysilyl group-containing compound (B2) is 1.1 parts by mass or more and 10 parts by mass or less per 100 parts by mass of the styrene-based elastomer (A) and the radically polymerizable compound (B) combined.

2. The composition according to claim 1, wherein the styrene elastomer (A) is an elastomer having structural units derived from butadiene.

3. The composition according to claim 1, wherein the ethylenically unsaturated bond-containing group of the modified polyphenylene ether (B1) having an ethylenically unsaturated bond-containing group at its terminal is a vinylbenzyl group.

4. The composition according to claim 1, wherein the ethylenically unsaturated bond and alkoxysilyl group-containing compound (B2) comprises a vinyl-based silane coupling agent.

5. The composition of claim 1, which is peroxide-free.

6. A cured product of the composition according to any one of claims 1 to 5.

7. An adhesive comprising the composition according to any one of claims 1 to 5.