Two-pack type resin composition

Abstract

The purpose of the present invention is to provide a two-pack type resin composition which can achieve both an extension in the curing time of the two-pack resin composition and a high monomer conversion rate. The present invention is a two-pack type resin composition comprising a liquid A and a liquid B. The liquid A contains a polymerizable monomer and a reaction accelerator. The polymerizable monomer includes an aromatic vinyl monomer. The content of the aromatic vinyl monomer is more than 0 mass% and not more than 60 mass% relative to 100 mass% of the polymerizable monomer. The liquid B contains an initiator.

Description

Two-component resin composition

[0001] The present invention relates to a two-component resin composition, and more particularly to a two-component resin composition useful as a heat dissipating material or the like.

[0002] In recent years, the performance of electronic devices such as automobile batteries and personal computers has improved, resulting in increased heat generation, creating a demand for heat dissipation materials that can efficiently dissipate heat. Known examples of heat dissipation materials include thermally conductive compositions in which a metal filler is dispersed in a resin. Regarding resin compositions for heat dissipation materials, Patent Document 1 discloses a two-component resin composition for heat dissipation materials that includes a liquid A and a liquid B, in which the liquid A contains a (meth)acrylic polymer, a radically polymerizable monomer, a reaction accelerator, and at least one crosslinking agent selected from the group consisting of a (meth)acrylate crosslinking agent and an allyl crosslinking agent, and the liquid B contains a (meth)acrylic polymer and a peroxide polymerization initiator.

[0003] International Publication No. 2021 / 039749

[0004] As described above, two-component resin compositions for use in heat dissipation materials have been developed in the past, but because systems that are cured by radical polymerization have short curing times, it is necessary to extend the curing time from the viewpoint of workability. In response to such needs, the present inventors discovered a new problem in that, although adding an inhibitor could delay curing for a certain period of time, it also reduced the monomer conversion rate (monofunctional monomer conversion rate).

[0005] The present invention has been made in consideration of the above-mentioned current situation, and aims to provide a two-component resin composition that can achieve both an extended curing time and a high monomer conversion rate.

[0006] The present inventors have conducted extensive research into two-component resin compositions and have found that a two-component resin composition consisting of a component A containing a polymerizable monomer and a reaction accelerator, wherein the ratio of aromatic vinyl monomer in the polymerizable monomer is within a predetermined range, and a component B containing an initiator, can achieve both an extended curing time and a high monomer conversion rate. They have come to the conclusion that this can brilliantly solve the above-mentioned problems and have arrived at the present invention.

[0007] The present invention includes the following two-component resin compositions, etc. [1] A two-component resin composition consisting of a component A and a component B, wherein the component A contains a polymerizable monomer and a reaction accelerator, the polymerizable monomer including an aromatic vinyl monomer, and the content of the aromatic vinyl monomer is greater than 0% by mass and not more than 60% by mass, relative to 100% by mass of the polymerizable monomer; and the component B contains an initiator. [2] The two-component resin composition according to the above component [1], wherein the polymerizable monomer includes a monomer having a glass transition temperature of -180 to -20°C when homopolymerized. [3] The two-component resin composition according to the above component [1] or [2], wherein the polymerizable monomer includes a (meth)acrylate having a hydrocarbon group having 4 to 15 carbon atoms, which may have a substituent. [4] The two-component resin composition according to any one of [1] to [3] above, wherein the content of the initiator is 1.5% by mass or more relative to 100% by mass of the polymerizable monomer. [5] The two-component resin composition according to any one of [1] to [4] above, wherein the polymerizable monomer includes a monomer having two or more polymerizable unsaturated bonds. [6] The two-component resin composition according to any one of [1] to [5] above, wherein the reaction accelerator includes a metal compound. [7] The two-component resin composition according to any one of [1] to [6] above, wherein the component B contains a reaction accelerator aid, and the reaction accelerator aid includes a diketone compound. [8] The two-component resin composition according to any one of [1] to [7] above, wherein the content of the polymerizable monomer is 40 to 99.9% by mass relative to 100% by mass of the total amount of the component A (excluding inorganic particles, if any, in the component A). [9] The two-component resin composition according to any one of [1] to [8] above, wherein the A-component and / or B-component contains a (meth)acrylic polymer.

[10] The two-component resin composition according to any one of [1] to [9] above, wherein the A-component and / or B-component contains a plasticizer.

[11] The two-component resin composition according to any one of [1] to

[10] above, wherein the A-component and / or B-component contains inorganic particles.

[12] The two-component resin composition according to any one of [1] to

[11] above, which is used for a heat dissipation material.

[0008] The two-component resin composition of the present invention has the above-mentioned configuration and can achieve both an extended curing time of the two-component resin composition and a high monomer conversion rate, and therefore can be suitably used, for example, as a resin for heat dissipation materials, an adhesive, a pressure-sensitive adhesive, etc.

[0009] Preferred embodiments of the present invention will be specifically described below, but the present invention is not limited to the following description and can be appropriately modified and applied within the scope of the present invention. Note that a combination of two or more of the individual preferred embodiments of the present invention described below also falls within the scope of the present invention.

[0010] The two-component resin composition of the present invention is a two-component resin composition consisting of a component A and a component B. A cured product or the like can be obtained by reacting components A and B.

[0011] The liquid A contains a polymerizable monomer and a reaction accelerator, the polymerizable monomer contains an aromatic vinyl monomer, and the content of the aromatic vinyl monomer is more than 0% by mass and 60% by mass or less, based on 100% by mass of the polymerizable monomer. The liquid B contains an initiator.

[0012] The content of the polymerizable monomer in the above-mentioned Liquid A is not particularly limited, but when Liquid A does not contain inorganic particles, it is preferably 40 to 99.9% by mass, based on 100% by mass of the total amount of Liquid A. It is more preferably 42 to 90% by mass, even more preferably 44 to 80% by mass, even more preferably 45 to 70% by mass, even more preferably 46 to 65% by mass, and particularly preferably 47 to 60% by mass. When Liquid A contains inorganic particles, it is preferably 40 to 99.9% by mass, based on 100% by mass of the total amount of Liquid A excluding the inorganic particles. It is more preferably 42 to 90% by mass, even more preferably 44 to 80% by mass, even more preferably 45 to 70% by mass, even more preferably 46 to 65% by mass, and particularly preferably 47 to 60% by mass. Furthermore, it is preferably 0.8 to 40% by mass, based on 100% by mass of the total amount of Liquid A including the inorganic particles. It is more preferably 1.0 to 30% by mass, even more preferably 1.5 to 20% by mass, and particularly preferably 2.0 to 12.0% by mass.

[0013] The content of the aromatic vinyl monomer is preferably 1 to 60% by mass, more preferably 2 to 55% by mass, and even more preferably 4 to 50% by mass, based on 100% by mass of the polymerizable monomer. In one aspect, the content of the aromatic vinyl monomer is 5 to 40% by mass, or 6 to 30% by mass, based on 100% by mass of the polymerizable monomer, which is also one of the preferred embodiments of the present invention.

[0014] The content of the reaction accelerator is not particularly limited, but when Liquid A does not contain inorganic particles, it is preferably 0.001 to 5% by mass, based on 100% by mass of the total amount of Liquid A. It is more preferably 0.01 to 3% by mass, and even more preferably 0.02 to 2% by mass. When Liquid A contains inorganic particles, it is preferably 0.001 to 5% by mass, based on 100% by mass of the total amount of Liquid A excluding the inorganic particles. It is more preferably 0.01 to 3% by mass, and even more preferably 0.02 to 2% by mass. Furthermore, it is preferably 0.00002 to 2% by mass, based on 100% by mass of the total amount of Liquid A including the inorganic particles. It is more preferably 0.0002 to 1% by mass, and even more preferably 0.001 to 0.3% by mass. When a metal compound is contained in the reaction accelerator, the mass of the metal compound in this specification is calculated in terms of the mass of the metal.

[0015] The content of the reaction accelerator is preferably 0.001 to 10% by mass, more preferably 0.005 to 8% by mass, even more preferably 0.01 to 6% by mass, and particularly preferably 0.02 to 4% by mass, relative to 100% by mass of the polymerizable monomer.

[0016] The content of the reaction accelerator is preferably 0.1 to 500% by mass, more preferably 0.2 to 250% by mass, even more preferably 0.4 to 100% by mass, still more preferably 0.5 to 80% by mass, still more preferably 1 to 75% by mass, and particularly preferably 1.5 to 70% by mass, relative to 100% by mass of the initiator in Solution B.

[0017] When a metal compound is used as the reaction accelerator, the content is not particularly limited. However, when Liquid A does not contain inorganic particles, the content is preferably 0.001 to 2 mass% relative to 100 mass% of the total amount of Liquid A. It is more preferably 0.01 to 1 mass%, and even more preferably 0.02 to 0.3 mass%. When Liquid A contains inorganic particles, the content of the reaction accelerator is preferably 0.001 to 2 mass% relative to 100 mass% of the total amount of Liquid A excluding the inorganic particles. It is more preferably 0.01 to 1 mass%, and even more preferably 0.02 to 0.3 mass%. Furthermore, the content of the reaction accelerator is preferably 0.0001 to 0.4 mass% relative to 100 mass% of the total amount of Liquid A including the inorganic particles. It is more preferably 0.001 to 0.2 mass%, and even more preferably 0.002 to 0.06 mass%.

[0018] When an accelerator other than a metal compound is used as the reaction accelerator, the content is not particularly limited. However, when inorganic particles are not contained in Liquid A, the content is preferably 0.01 to 5 mass% relative to 100 mass% of the total amount of Liquid A. It is more preferably 0.05 to 4 mass%, and even more preferably 0.1 to 3 mass%. When inorganic particles are contained in Liquid A, the content of the reaction accelerator is preferably 0.01 to 5 mass% relative to 100 mass% of the total amount of Liquid A excluding the inorganic particles. It is more preferably 0.05 to 4 mass%, and even more preferably 0.1 to 3 mass%. Furthermore, the content of the reaction accelerator is preferably 0.0001 to 1 mass% relative to 100 mass% of the total amount of Liquid A including the inorganic particles. It is more preferably 0.005 to 0.8 mass%, and even more preferably 0.01 to 0.6 mass%.

[0019] Furthermore, when a metal compound is used as the reaction accelerator, the content is preferably 0.005 to 5 mass% relative to 100 mass% of the polymerizable monomer. More preferably, it is 0.01 to 3 mass%, even more preferably, it is 0.03 to 1 mass%, and particularly preferably, it is 0.05 to 0.5 mass%. When an accelerator other than a metal compound is used as the reaction accelerator, the content is preferably 0.05 to 10 mass% relative to 100 mass% of the polymerizable monomer. More preferably, it is 0.1 to 8 mass%, even more preferably, it is 0.3 to 6 mass%, and particularly preferably, it is 0.5 to 5 mass%.

[0020] When a metal compound is used as the reaction accelerator, the content is preferably 0.1 to 100% by mass relative to 100% by mass of the initiator in Solution B. It is more preferably 0.2 to 60% by mass, even more preferably 0.4 to 40% by mass, even more preferably 0.6 to 20% by mass, even more preferably 0.8 to 15% by mass, and particularly preferably 1 to 10% by mass. When an accelerator other than a metal compound is used as the reaction accelerator, the content is preferably 1 to 300% by mass relative to 100% by mass of the initiator in Solution B. It is more preferably 2 to 250% by mass, even more preferably 4 to 200% by mass, even more preferably 6 to 150% by mass, and particularly preferably 10 to 100% by mass.

[0021] The content of the initiator is not particularly limited, but is preferably 1.5 to 50% by mass relative to 100% by mass of the polymerizable monomer. This allows the resin composition to be cured more sufficiently, and odors derived from the aromatic vinyl monomer can be more sufficiently suppressed. The content of the initiator is more preferably 2 to 30% by mass, even more preferably 2.5 to 20% by mass, and particularly preferably 3 to 12% by mass.

[0022] As described below, the above-mentioned component B preferably contains a reaction accelerator. The total proportion of the initiator, reaction accelerator, and reaction accelerator in the above-mentioned two-component resin composition is preferably 2 to 50% by mass, more preferably 4 to 30% by mass, and even more preferably 6 to 25% by mass, relative to 100% by mass of the polymerizable monomer.

[0023] The total proportion of the reaction accelerator and reaction accelerator aid in the two-component resin composition is preferably 10 to 2000% by mass, more preferably 15 to 1000% by mass, even more preferably 20 to 500% by mass, still more preferably 50 to 400% by mass, and even more preferably 80 to 350% by mass, relative to 100% by mass of the initiator.

[0024] The total proportion of the initiator, the reaction accelerator using a metal compound, and the reaction acceleration aid in the two-component resin composition is preferably 2 to 50% by mass, more preferably 4 to 40% by mass, and even more preferably 5 to 30% by mass, relative to 100% by mass of the polymerizable monomer. The total proportion of the initiator, the reaction accelerator other than a metal compound, and the reaction acceleration aid in the two-component resin composition is preferably 2 to 50% by mass, more preferably 4 to 40% by mass, and even more preferably 5 to 30% by mass, relative to 100% by mass of the polymerizable monomer.

[0025] The total proportion of the reaction accelerator and reaction accelerator aid using a metal compound in the two-component resin composition is preferably 10 to 2000% by mass, based on 100% by mass of the initiator. It is more preferably 15 to 1000% by mass, even more preferably 20 to 500% by mass, even more preferably 50 to 400% by mass, and even more preferably 100 to 350% by mass. The total proportion of the reaction accelerator and reaction accelerator aid other than a metal compound in the two-component resin composition is preferably 10 to 2000% by mass, based on 100% by mass of the initiator. It is more preferably 15 to 1000% by mass, even more preferably 20 to 500% by mass, even more preferably 50 to 400% by mass, and even more preferably 100 to 350% by mass.

[0026] As described below, the reaction accelerator in Solution A preferably contains a metal compound. The proportion of the metal compound in the reaction accelerator is preferably 1 to 100% by mass, relative to 100% by mass of the reaction accelerator. It is more preferably 50 to 100% by mass, even more preferably 70 to 100% by mass, particularly preferably 80 to 100% by mass, and most preferably 100% by mass. In one aspect, the proportion of the metal compound in the reaction accelerator is preferably 1 to 100% by mass, relative to 100% by mass of the reaction accelerator. It is more preferably 1 to 80% by mass, even more preferably 2 to 60% by mass, particularly preferably 4 to 50% by mass, and even more preferably 5 to 40% by mass.

[0027] The reaction-accelerating aid in Solution B preferably contains a diketone compound. The content of the diketone compound is not particularly limited, but is preferably 1 to 600 mol per 1 mol of the metal compound. It is more preferably 5 to 400 mol, even more preferably 10 to 200 mol, and particularly preferably 12 to 50 mol.

[0028] The total proportion of the diketone compound and the metal in the metal compound in the two-component resin composition is preferably 10 to 2000% by mass, more preferably 15 to 1000% by mass, even more preferably 20 to 500% by mass, still more preferably 50 to 400% by mass, still more preferably 100 to 350% by mass, and particularly preferably 100 to 300% by mass, relative to 100% by mass of the initiator.

[0029] The total content of the diketone compound, the metal in the metal compound, and the initiator is preferably 2 to 50% by mass, more preferably 4 to 40% by mass, even more preferably 5 to 30% by mass, and particularly preferably 6 to 25% by mass, relative to 100% by mass of the polymerizable monomer.

[0030] The liquid A and / or liquid B preferably contain a (meth)acrylic polymer, as described below. The content of the (meth)acrylic polymer in the two-component resin composition is not particularly limited. However, when liquid A and liquid B do not contain inorganic particles, the content is preferably 0 to 60% by mass relative to 100% by mass of the two-component resin composition (total amount of liquid A and liquid B). It is more preferably 0 to 40% by mass, and even more preferably 10 to 30% by mass. When liquid A or liquid B contains inorganic particles, the content of the (meth)acrylic polymer is preferably 0 to 60% by mass relative to 100% by mass of the two-component resin composition (total amount of liquid A and liquid B) excluding the inorganic particles. It is more preferably 0 to 40% by mass, and even more preferably 10 to 30% by mass. The content of the (meth)acrylic polymer is preferably 0 to 24% by mass relative to 100% by mass of the two-component resin composition (total amount of liquid A and liquid B) containing inorganic particles. The content is more preferably 0 to 10% by mass, and even more preferably 0.5 to 4.5% by mass.

[0031] The content of the (meth)acrylic polymer in the two-component resin composition is preferably 0 to 150% by mass, more preferably 25 to 120% by mass, and even more preferably 50 to 100% by mass, relative to 100% by mass of the polymerizable monomer.

[0032] The liquid A and / or liquid B preferably contain a plasticizer, as described below. The content of the plasticizer is not particularly limited, but when liquid A and liquid B do not contain inorganic particles, it is preferably 10 to 80% by mass relative to 100% by mass of the two-component resin composition (total amount of liquid A and liquid B). It is more preferably 25 to 70% by mass, and even more preferably 40 to 60% by mass. When liquid A or liquid B contains inorganic particles, it is preferably 10 to 80% by mass relative to 100% by mass of the two-component resin composition (total amount of liquid A and liquid B) excluding the inorganic particles. It is more preferably 25 to 70% by mass, and even more preferably 40 to 60% by mass. The content of the plasticizer is preferably 0.2 to 32% by mass relative to 100% by mass of the two-component resin composition (total amount of liquid A and liquid B) containing inorganic particles. It is more preferably 1 to 20% by mass, and even more preferably 2 to 10% by mass.

[0033] The content of the plasticizer is preferably 50 to 700% by mass, more preferably 80 to 600% by mass, even more preferably 100 to 500% by mass, and particularly preferably 150 to 400% by mass, relative to 100% by mass of the (meth)acrylic polymer in the two-component resin composition.

[0034] The content of the plasticizer is preferably 20 to 500% by mass, more preferably 50 to 400% by mass, even more preferably 80 to 300% by mass, and particularly preferably 100 to 250% by mass, relative to 100% by mass of the polymerizable monomer.

[0035] As described below, the above-mentioned Liquid A and / or Liquid B preferably contain inorganic particles. The content of the inorganic particles is not particularly limited, but is preferably 60 to 98% by mass relative to 100% by mass of the two-component resin composition (total amount of Liquid A and Liquid B). This results in the obtained cured product having superior thermal conductivity. The content of the inorganic particles is more preferably 75 to 97% by mass, even more preferably 80 to 96% by mass, and particularly preferably 85 to 95% by mass.

[0036] The content of the inorganic particles is preferably 400 to 5000% by mass, more preferably 500 to 4500% by mass, even more preferably 600 to 4000% by mass, still more preferably 800 to 3500% by mass, and particularly preferably 1000 to 3000% by mass, relative to 100% by mass of the total amount of the (meth)acrylic polymer and polymerizable monomer in the two-component resin composition.

[0037] The above-mentioned liquid A and / or liquid B may contain other additives as described below. The content of the other additives in the above-mentioned two-component resin composition is not particularly limited. However, when liquid A and liquid B do not contain inorganic particles, the content of the other additives is preferably 0 to 30% by mass relative to 100% by mass of the two-component resin composition (total amount of liquid A and liquid B). It is more preferably 0 to 20% by mass, even more preferably 0 to 10% by mass, and particularly preferably 0 to 5% by mass. When liquid A or liquid B contains inorganic particles, the content of the other additives is preferably 0 to 30% by mass relative to 100% by mass of the two-component resin composition (total amount of liquid A and liquid B) excluding the inorganic particles. It is more preferably 0 to 20% by mass, even more preferably 0 to 10% by mass, and particularly preferably 0 to 5% by mass. Furthermore, the content of the other additives is preferably 0 to 12% by mass relative to 100% by mass of the two-component resin composition (total amount of liquid A and liquid B) containing inorganic particles. It is more preferably 0 to 6% by mass, even more preferably 0 to 2% by mass, and particularly preferably 0 to 1% by mass.

[0038] The essential components and optional components contained in the two-component resin composition of the present invention will be further described below.

[0039] <Solution A> The solution A contains a polymerizable monomer and a reaction accelerator, and the polymerizable monomer includes an aromatic vinyl monomer, and the content of the aromatic vinyl monomer is more than 0% by mass and not more than 60% by mass relative to 100% by mass of the polymerizable monomer. (Polymerizable Monomer) The polymerizable monomer is a monomer having at least one polymerizable unsaturated bond. By including the aromatic vinyl monomer in the polymerizable monomer in the above ratio, it is possible to extend the curing time while maintaining a high monomer conversion rate. The aromatic vinyl monomer is not particularly limited as long as it is a compound having a polymerizable unsaturated bond and an aromatic group, but is preferably a compound represented by the following formula (1);

[0040]

[0041] (In the formula, R １ , R ２ , R ３ are the same or different and represent a hydrogen atom or an alkyl group having 1 to 3 carbon atoms. ４ represents an aryl group or aralkyl group having 6 to 20 carbon atoms, which may have a substituent. The alkyl group is preferably a methyl group, an ethyl group, or a propyl group, and has 1 or 2 carbon atoms, more preferably a methyl group or an ethyl group, and even more preferably a methyl group. １ , R ２ and R ３ are preferably the same or different and each is a hydrogen atom or a methyl group. More preferably, R １ , R ２ is a hydrogen atom, and R ３ is a hydrogen atom or a methyl group.

[0042] Examples of the aryl group include a phenyl group, a naphthyl group, an anthryl group, a biphenyl group, a triphenyl group, and groups having one or more alkyl groups attached thereto. Of these, a phenyl group and a group having an alkyl group having 1 to 5 carbon atoms attached thereto are preferred. Examples of the aralkyl group include a benzyl group, a phenethyl group, a phenylpropyl group, a phenylpentyl group, a phenylhexyl group, and a phenyloctyl group.

[0043] The substituents that the aryl group and the aralkyl group may have are not particularly limited, but examples thereof include a hydroxyl group, a carboxyl group, a sulfonic acid group, an amide group, a thiol group, a halogen group, and an ether group.

[0044] The number of carbon atoms in the aryl group and the aralkyl group is preferably 6 to 18, more preferably 6 to 12, even more preferably 6 to 10, and still more preferably 6 to 8. The number of carbon atoms includes the number of carbon atoms in the substituent.

[0045] The above R ４ is preferably an aryl group, more preferably a phenyl group or an alkylphenylene group. The alkyl group in the alkylphenylene group is not particularly limited, and examples thereof include the above-mentioned alkyl groups having 1 to 3 carbon atoms and the alkyl groups having 4 to 14 carbon atoms described below. ４ More preferred are a phenyl group and a methylphenylene group.

[0046] The aromatic vinyl monomer is preferably styrene, α-methylstyrene, vinyltoluene, ethylstyrene, t-butylstyrene, vinylnaphthalene, vinylbiphenyl, etc., and more preferably styrene, α-methylstyrene, and vinyltoluene.

[0047] The polymerizable monomer preferably contains a monomer having a glass transition temperature of -180 to -20°C when homopolymerized. This increases the flexibility of the cured product, and when the resin composition is used as a heat dissipation material, it is possible to more sufficiently increase the ability of the heat dissipation material to conform to a heat generating body and a heat dissipation body. The glass transition temperature is preferably -160 to -30°C. The glass transition temperature means a temperature calculated based on the Fox equation described below.

[0048] The monomer having a glass transition temperature of −180 to −20° C. when homopolymerized is not particularly limited, and examples thereof include (meth)acrylates having a hydrocarbon group having 4 to 15 carbon atoms which may have a substituent, as described below, hydroxyethyl (meth)acrylate, and 4-hydroxybutyl (meth)acrylate.

[0049] The polymerizable monomer preferably contains a (meth)acrylate having a hydrocarbon group of 4 to 15 carbon atoms, which may have a substituent. The (meth)acrylate having a hydrocarbon group of 4 to 15 carbon atoms, which may have a substituent, has a bulky structure, and therefore, in this case too, the flexibility of the cured product can be increased, and when used as a heat dissipation material, the ability of the heat dissipation material to conform to a heat generating body and a heat dissipation body can be more sufficiently increased.

[0050] The (meth)acrylate having a hydrocarbon group having 4 to 15 carbon atoms may have a substituent. The substituent is not particularly limited, but examples thereof include a hydroxyl group, an alkoxy group, a carboxyl group, an acyl group, a sulfonic acid group, an amino group, a phosphate group, an ether group, a thiol group, a thioether group, and a halogen group.

[0051] In the (meth)acrylate having a hydrocarbon group having 4 to 15 carbon atoms, which may have a substituent, the number of carbon atoms in the hydrocarbon group may be 4 to 15, but the number of carbon atoms in the hydrocarbon group includes the number of carbon atoms in the substituent. The number of carbon atoms in the hydrocarbon group is preferably 4 to 12, more preferably 4 to 10, and even more preferably 4 to 8.

[0052] Examples of the hydrocarbon group in the (meth)acrylate include an alkyl group, an alkenyl group, an alkynyl group, an aryl group, an aralkyl group, etc. The hydrocarbon group is preferably one that does not have a substituent.

[0053] Examples of alkyl groups having 4 to 15 carbon atoms include n-butyl, n-pentyl (amyl), n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, n-nonadecyl, n-eicosanyl, i-propyl, sec-butyl, i-butyl, t-butyl, 1-methylbutyl, 1-ethylpropyl, 2-methylbutyl, i-amyl, neopentyl, 1,2-dimethylpropyl, 1,1-dimethylpropyl, t-amyl, 1,3-dimethylbutyl, and 3,3-dimethylbutyl. aliphatic alkyl groups such as a 2-ethylbutyl group, a 2-ethyl-2-methylpropyl group, a 1-methylheptyl group, a 2-ethylhexyl group, a 1,5-dimethylhexyl group, a t-octyl group, a 2,6-dimethyloctyl group, a 2-butyloctyl group, a branched nonyl group, a decyl group, an undecyl group, a dodecyl group, a tridecyl group, a tetradecyl group, or a pentadecyl group; and alicyclic alkyl groups such as a cyclopropylmethyl group, a cyclobutyl group, a cyclobutylmethyl group, a cyclopentyl group, a cyclohexyl group, a cyclohexylmethyl group, a cycloheptyl group, a cyclooctyl group, a cyclohexylpropyl group, a cyclododecyl group, a norbornyl group (C7), an adamantyl group (C10), or a cyclopentylethyl group.

[0054] Examples of alkenyl groups having 4 to 15 carbon atoms include 1-butenyl, 2-butenyl, pentenyl, hexenyl, heptenyl, octenyl, nonenyl, decenyl, dodecenyl, tridecenyl, tetradecenyl, and pentadecenyl groups.

[0055] Examples of alkynyl groups having 4 to 15 carbon atoms include butynyl, pentynyl, hexynyl, heptynyl, octynyl, nonynyl, decynyl, dodecynyl, tridecynyl, tetradecynyl, and pentadecynyl groups. Examples of aryl groups having 6 to 15 carbon atoms include phenyl, naphthyl, and anthracenyl groups. Examples of aralkyl groups having 6 to 15 carbon atoms include benzyl, 1-phenylethyl, 2-phenylethyl, 3-phenylpropyl, and 4-phenylbutyl groups.

[0056] The hydrocarbon group in the (meth)acrylate is preferably an alkyl group, more preferably a linear or branched aliphatic alkyl group, still more preferably a dodecyl group, an isodecyl group, a nonyl group, an isononyl group, an octyl group, a 1-methylheptyl group, a 2-ethylhexyl group, or a butyl group, and particularly preferably an octyl group, a 1-methylheptyl group, or a 2-ethylhexyl group.

[0057] Specific examples of the (meth)acrylate having a hydrocarbon group having 4 to 15 carbon atoms include butyl (meth)acrylate, pentyl (meth)acrylate, hexyl (meth)acrylate, heptyl (meth)acrylate, octyl (meth)acrylate, nonyl (meth)acrylate, isononyl (meth)acrylate, decyl (meth)acrylate, isodecyl (meth)acrylate, undecyl (meth)acrylate, dodecyl (meth)acrylate, tridecyl (meth)acrylate, tetradecyl (meth)acrylate, pentadecyl (meth)acrylate, methylbutyl (meth)acrylate, dimethylpropyl (meth)acrylate, dimethylbutyl (meth)acrylate, ethylbutyl (meth)acrylate, methylpropyl (meth)acrylate, methylheptyl (meth)acrylate, ethylhexyl (meth)acrylate, and dimethylhexyl (meth)acrylate. Preferred are dodecyl (meth)acrylate, isodecyl (meth)acrylate, nonyl (meth)acrylate, isononyl (meth)acrylate, octyl (meth)acrylate, 1-methylheptyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, and butyl (meth)acrylate, and more preferred are octyl (meth)acrylate, 1-methylheptyl (meth)acrylate, and 2-ethylhexyl (meth)acrylate.

[0058] The polymerizable monomer preferably includes a monomer having two or more polymerizable unsaturated bonds. Such a monomer acts as a crosslinking agent in the resin composition, and can more fully cure the resin composition. Examples of the monomer having two or more polymerizable unsaturated bonds include a polyfunctional (meth)acrylate having two or more (meth)acrylate groups, a polyfunctional allyl ester having two or more allyl groups, and a polyfunctional allyl ether having two or more allyl groups.

[0059] Examples of the polyfunctional (meth)acrylate include (poly)ethylene glycol di(meth)acrylates such as tetraethylene glycol di(meth)acrylate, (poly)propylene glycol di(meth)acrylate, neopentyl glycol di(meth)acrylate, 1,9-nonanediol di(meth)acrylate, 1,6-hexanediol di(meth)acrylate, 1,4-butanediol di(meth)acrylate, and bifunctional (meth)acrylates such as trimethylolpropane di(meth)acrylate. acrylates; trifunctional (meth)acrylates such as (meth)acrylate group-containing cyanurate compounds such as trimethylolpropane tri(meth)acrylate, pentaerythritol tri(meth)acrylate, and tris(2-acryloyloxyethyl) isocyanurate; pentaerythritol tetra(meth)acrylate, ethoxylated pentaerythritol tetra(meth)acrylate, dipentaerythritol penta(meth)acrylate, and dipentaerythritol hexa(meth)acrylate.

[0060] Examples of the polyfunctional allyl esters include allyl group-containing cyanurate compounds such as triallyl isocyanurate and triallyl cyanurate; and aliphatic polyfunctional allyl esters such as diallyl oxalate, diallyl malonate, diallyl succinate, diallyl glutarate, diallyl adipate, diallyl pimelate, diallyl suberate, diallyl azelate, diallyl sebacate, diallyl fumarate, diallyl maleate, triallyl citrate, diallyl tartrate, diallyl itaconate, diallyl citraconate, and triallyl trimellitate.

[0061] Examples of the polyfunctional allyl ethers include diallyl ether, glycerin diallyl ether, glycerin triallyl ether, 1,4-butanediol diallyl ether, nonanediol diallyl ether, 1,4-cyclohexane dimethanol diallyl ether, triethylene glycol diallyl ether, trimethylolpropane diallyl ether, trimethylolpropane triallyl ether, ditrimethylolpropane tetraallyl ether, pentaerythritol diallyl ether, pentaerythritol triallyl ether, pentaerythritol tetraallyl ether, dipentaerythritol pentaallyl ether, dipentaerythritol hexaallyl ether, sorbitol diallyl ether, and 1,3-bis(allyloxy)aryl. Examples of the adamantane include damantane, 1,3,5-tris(allyloxy)adamantane, bisphenol S diallyl ether, bisphenol A diallyl ether, bisphenol A alkylene oxide diallyl ether, bisphenol F alkylene oxide diallyl ether, 2,5-diallylphenol allyl ether, allyl ether of novolac phenol, allylated polyphenylene oxide, a compound in which the glycidyl group of an epoxy resin is substituted with an allyl group, 1,1,2,2-tetraallyloxyethane, ethylene glycol diallyl ether, diethylene glycol diallyl ether, polyethylene glycol diallyl ether, propylene glycol diallyl ether, butylene glycol diallyl ether, and hexanediol diallyl ether.

[0062] The monomer having two or more polymerizable unsaturated bonds is preferably a polyfunctional (meth)acrylate or a polyfunctional allyl ester, more preferably a (meth)acrylate group-containing cyanurate compound or an allyl group-containing cyanurate compound, and even more preferably tris(2-acryloyloxyethyl) isocyanurate or triallyl isocyanurate.

[0063] The polymerizable monomer may include other polymerizable monomers other than aromatic vinyl monomers, monomers having a glass transition temperature of −180 to −20° C. when homopolymerized, (meth)acrylates having a hydrocarbon group of 4 to 15 carbon atoms which may have a substituent, and monomers having two or more polymerizable unsaturated bonds. Examples of other polymerizable monomers include, but are not limited to, alkyl (meth)acrylates having 1 to 3 carbon atoms such as methyl (meth)acrylate, ethyl (meth)acrylate, and propyl (meth)acrylate; vinyl group-containing monomers such as N-vinyl-2-pyrrolidone; and reactive light stabilizers such as 1,2,2,6,6-pentamethyl-4-piperidyl methacrylate and 2,2,6,6-tetramethyl-4-piperidyl methacrylate.

[0064] The content of the monomer having a glass transition temperature of −180 to −20° C. when homopolymerized is not particularly limited, but is preferably 30 to 99.5% by mass, more preferably 35 to 99% by mass, even more preferably 40 to 98% by mass, and particularly preferably 50 to 97% by mass, relative to 100% by mass of the polymerizable monomer.

[0065] The content of the (meth)acrylate having a hydrocarbon group of 4 to 15 carbon atoms, which may have a substituent, is not particularly limited, but is preferably 30 to 99.5% by mass, more preferably 35 to 99% by mass, even more preferably 40 to 98% by mass, and particularly preferably 50 to 97% by mass, relative to 100% by mass of the polymerizable monomer.

[0066] The content of the monomer having two or more polymerizable unsaturated bonds is not particularly limited, but is preferably 0.1 to 10% by mass, more preferably 0.2 to 8% by mass, even more preferably 0.5 to 6% by mass, and particularly preferably 1 to 4% by mass, relative to 100% by mass of the polymerizable monomer.

[0067] The content of the other polymerizable monomers is not particularly limited, but is preferably 0 to 10% by mass, more preferably 0 to 5% by mass, even more preferably 0 to 1% by mass, particularly preferably 0 to 0.1% by mass, and most preferably 0% by mass, relative to 100% by mass of the polymerizable monomers.

[0068] (Reaction Accelerator) The reaction accelerator preferably contains a metal compound. This can more sufficiently increase the monomer conversion rate during curing. The metal compound may contain a transition metal element such as cobalt, iron, manganese, copper, zinc, titanium, chromium, vanadium, or zirconium, but a salt (complex) of an organic compound having 4 to 20 carbon atoms with the transition metal element is preferred. Specific examples of the metal compound include metal soaps such as cobalt naphthenate, iron naphthenate, manganese naphthenate, copper naphthenate, zinc naphthenate, cobalt octylate, iron octylate, cobalt neodecanoate, copper neodecanoate, cobalt acetylacetonate, copper acetylacetonate, titanium acetylacetonate, manganese acetylacetonate, chromium acetylacetonate, iron acetylacetonate, and vanadyl acetylacetonate. The metal element in the metal compound is preferably cobalt, iron, or manganese, and more preferably cobalt. The metal compound is preferably cobalt naphthenate, cobalt octylate, or cobalt acetylacetonate, and more preferably cobalt naphthenate or cobalt octylate.

[0069] The reaction accelerator may contain a compound other than the metal compound. The reaction accelerator other than the metal compound is not particularly limited, but examples thereof include imidazole, 2-methylimidazole, 2-undecylimidazole, 2-heptadecylimidazole, 1,2-dimethylimidazole, 2-ethyl-4-methylimidazole, 2-phenylimidazole, 2-phenyl-4-methylimidazole, 1-benzyl-2-methylimidazole, 1-benzyl-2-phenylimidazole, and 1-cyanoethyl-2-methylimidazoline. compounds having an imidazole skeleton such as aniline, N,N-dimethylaniline, N,N-diethylaniline, m-toluidine, p-toluidine, N-ethyl-m-toluidine, N,N-dimethyl compounds having an aniline skeleton such as N-p-toluidine, N,N-bis(2-hydroxyethyl)-p-toluidine, N,N-bis(2-hydroxypropyl)-p-toluidine, and N,N-bis(hydroxyethyl)aniline; compounds having an alkanolamine skeleton such as p-tolyldiethanolamine, N-phenyl-N'-ethylethanolamine, N-phenyldiethanolamine, triethanolamine, and diethanolaniline; diethylenetriamine, 4-(N,N-dimethylamino)benzaldehyde, 4-[N,N-bis(2-hydroxyethyl)amino]benzaldehyde, 4-(N-methyl-N-hydroxyethylamino)benzaldehyde, pyridine, piperidine, and phenylmorpholine; and thiourea compounds such as ethylenethiourea, diethylthiourea, dibutylthiourea, tetramethylthiourea, N-acetylthiourea, N-benzoylthiourea, diphenylthiourea, and dicyclohexylthiourea.

[0070] As the other reaction accelerators, compounds having an alkanolamine skeleton and thiourea compounds are preferred. As compounds having an alkanolamine skeleton, compounds having an ethanolamine skeleton are more preferred, and p-tolyldiethanolamine and N-phenyldiethanolamine are even more preferred. As thiourea compounds, dialkylthioureas are preferred, and dibutylthiourea is more preferred.

[0071] (Plasticizer) The liquid A preferably contains a plasticizer, which makes the resin composition excellent in processability even when no solvent is used.Trimellitic acid triester plasticizers such as tri-2-ethylhexyl trimellitate, tri-n-octyl trimellitate, and triisononyl trimellitate; phthalate ester plasticizers such as dimethyl phthalate, diethyl phthalate, dibutyl phthalate, dihexyl phthalate, dioctyl phthalate, diisononyl phthalate, di-2-ethylhexyl phthalate, dibenzyl phthalate, diisodecyl phthalate, ditridecyl phthalate, and diundecyl phthalate; di-n-butyl adipate, diisobutyl adipate, and dibutoxyethyl Adipate ester-based plasticizers such as adipate, di-n-octyl adipate, diisooctyl adipate, diisononyl adipate, bis-2-ethylhexyl adipate, and diisodecyl adipate; phosphate ester-based plasticizers such as tributyl phosphate, tri(2-ethylhexyl) phosphate, trioctyl phosphate, triphenyl phosphate, diphenyl-2-ethylhexyl phosphate, and tricresyl phosphate; and sebacate esters such as dibutyl sebacate, dioctyl sebacate, and di-2-ethylhexyl sebacate. azelaic acid ester-based plasticizers such as dihexyl azelate and dioctyl azelate; citrate ester-based plasticizers such as triethyl citrate, acetyl triethyl citrate, and tri-n-butyl citrate; glycolic acid ester-based plasticizers such as methyl phthalyl ethyl glycolate and ethyl phthalyl ethyl glycolate; trimellitic acid triester-based plasticizers such as trioctyl trimellitate, tri-n-octyl-n-decyl trimellitate, and trialkyl trimellitate (alkyl group carbon number: 4 to 11); methyl acetyl lysine Examples of suitable plasticizers include ricinoleate ester-based plasticizers such as di-n-butyl maleate, butyl acetylricinoleate, and glycerin monoricinoleate; maleate ester-based plasticizers such as di-n-butyl maleate; itaconate ester-based plasticizers such as monobutyl itaconate; oleate ester-based plasticizers such as butyl oleate; and glycerin-based plasticizers such as glycerin monoacetomonolaurate, glycerin diacetomonolaurate, glycerin monoacetomonostearate, and glycerin diacetomonooleate, but the present invention is not limited to these examples.These plasticizers may be used alone or in combination of two or more. Among these plasticizers, trimellitic acid triester plasticizers are preferred from the viewpoint of preventing evaporation of the plasticizer and improving the thermal stability of the plasticizer over a long period of time.

[0072] ((Meth)acrylic polymer) The above-mentioned liquid A may contain a (meth)acrylic polymer. As will be described later, in the two-component resin composition of the present invention, liquid B may contain a (meth)acrylic polymer, or liquid A and / or liquid B may contain a (meth)acrylic polymer. This form is one of the preferred embodiments of the present invention.

[0073] The (meth)acrylic polymer has a structural unit derived from a (meth)acrylic monomer. The structural unit derived from a (meth)acrylic monomer is a unit having a structure in which the carbon-carbon double bond of the (meth)acrylic monomer is replaced with a carbon-carbon single bond. The structural unit derived from a (meth)acrylic monomer can be introduced into the (meth)acrylic polymer by polymerizing the (meth)acrylic monomer. Examples of the (meth)acrylic monomer include alkyl (meth)acrylates and hydroxyl group-containing (meth)acrylates, but the present invention is not limited to these examples. These (meth)acrylic monomers may be used alone or in combination of two or more.

[0074] Examples of the alkyl (meth)acrylate include alkyl (meth)acrylates in which the alkyl group has 1 to 18 carbon atoms. Specific examples include methyl (meth)acrylate, ethyl (meth)acrylate, propyl (meth)acrylate, isopropyl (meth)acrylate, and the above-mentioned alkyl (meth)acrylates in which the alkyl group has 4 to 15 carbon atoms. These alkyl (meth)acrylates may be used alone or in combination of two or more. Among these alkyl (meth)acrylates, from the viewpoint of increasing the flexibility of the cured product and improving the conformability to heat-generating bodies and heat-dissipating bodies when the cured product is used as a heat-dissipating material, alkyl (meth)acrylates in which the alkyl group has 1 to 8 carbon atoms are preferred, and n-butyl (meth)acrylate, n-octyl (meth)acrylate, 1-methylheptyl (meth)acrylate, and 2-ethylhexyl (meth)acrylate are more preferred.

[0075] The content of the alkyl (meth)acrylate-derived structural units in the (meth)acrylic polymer is not particularly limited, but from the viewpoint of improving the conformability of the heat dissipating material to the heat generating element and the heat dissipating element, it is preferably 50% by mass or more, more preferably 60% by mass or more, even more preferably 70% by mass or more, and even more preferably 80% by mass or more, relative to 100% by mass of all structural units, with the upper limit being 100% by mass. Therefore, the content of alkyl (meth)acrylate in the (meth)acrylic monomer is preferably 50 to 100% by mass, more preferably 60 to 99% by mass, even more preferably 70 to 98% by mass, and particularly preferably 80 to 97% by mass.

[0076] Examples of hydroxyl group-containing (meth)acrylates include hydroxyl group-containing (meth)acrylates having an ester moiety containing 1 to 18 carbon atoms, such as 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 3-hydroxypropyl (meth)acrylate, 2-hydroxybutyl (meth)acrylate, 4-hydroxybutyl (meth)acrylate, and glycerin mono(meth)acrylate, but the present invention is not limited to these examples. These hydroxyl group-containing (meth)acrylates may be used alone or in combination of two or more. Of these hydroxyl group-containing (meth)acrylates, from the viewpoint of reactivity, 2-hydroxyethyl (meth)acrylate and glycerin mono(meth)acrylate are preferred, 2-hydroxyethyl (meth)acrylate is more preferred, and 2-hydroxyethyl acrylate is even more preferred. Furthermore, from the viewpoint of improving the dispersion stability of inorganic particles in Liquid A when the inorganic particles described below are contained in Liquid A, 2-hydroxyethyl (meth)acrylate and glycerin mono(meth)acrylate are preferred, 2-hydroxyethyl (meth)acrylate is more preferred, and 2-hydroxyethyl acrylate is even more preferred.

[0077] The content of structural units derived from hydroxyl group-containing (meth)acrylate in the (meth)acrylic polymer is preferably 0% by mass or more, more preferably 0.3% by mass or more, even more preferably 0.5% by mass or more, and even more preferably 1% by mass or more, relative to 100% by mass of all structural units, from the viewpoint of improving the dispersion stability of the resin composition and reducing the viscosity of the resin composition, and from the viewpoint of reducing the viscosity of the (meth)acrylic polymer and improving the compatibility between the (meth)acrylic monomer and the radically polymerizable monomer, it is preferably 30% by mass or less, more preferably 25% by mass or less, and even more preferably 20% by mass or less. Therefore, the content of hydroxyl group-containing (meth)acrylate in the (meth)acrylic monomer is preferably 0 to 30% by mass, more preferably 0.3 to 30% by mass, even more preferably 0.5 to 20% by mass, and even more preferably 1 to 20% by mass, relative to 100% by mass of all structural units.

[0078] The (meth)acrylic polymer may contain structural units derived from monomers other than the above-mentioned monomers, provided that the object of the present invention is not impaired. Examples of such other monomers include cycloalkyl (meth)acrylates such as cyclopropyl (meth)acrylate, cyclobutyl (meth)acrylate, cyclopentyl (meth)acrylate, cyclohexyl (meth)acrylate, and isobornyl (meth)acrylate, carbon-carbon double bond-containing monomers having a carboxyl group such as (meth)acrylic acid, carbon-carbon double bond-containing monomers having a silane group, carbon-carbon double bond-containing monomers having a nitrogen atom, carbon-carbon double bond-containing monomers having an oxo group, carbon-carbon double bond-containing monomers having a fluorine atom, carbon-carbon double bond-containing monomers having an epoxy group, carbon-carbon double bond-containing monomers having an aralkyl group, and aromatic monomers having a carbon-carbon double bond such as styrene.

[0079] The content of structural units derived from other monomers in the (meth)acrylic polymer is not particularly limited, but is preferably 0 to 10% by mass, more preferably 0 to 5% by mass, even more preferably 0 to 1% by mass, still more preferably 0 to 0.1% by mass, and most preferably 0% by mass, relative to 100% by mass of all structural units.

[0080] The (meth)acrylic polymer can be prepared by polymerizing a monomer component containing a (meth)acrylic monomer by a polymerization method such as bulk polymerization, solution polymerization, emulsion polymerization, etc. Among these polymerization methods, bulk polymerization is preferred from the viewpoint of preventing the inclusion of a solvent and a dispersion medium in the (meth)acrylic polymer.

[0081] The glass transition temperature of the (meth)acrylic polymer is preferably −20° C. or lower, more preferably −30° C. or lower, from the viewpoint of increasing the flexibility of the cured product and improving the conformability to a heat-generating body and a heat-dissipating body when the cured product is used as a heat-dissipating material. The lower limit of the glass transition temperature of the (meth)acrylic polymer is not particularly limited, but is preferably −200° C. or higher, more preferably −180° C. or higher.

[0082] In the present invention, the glass transition temperature of a polymer means a temperature calculated based on the Fox equation, which is expressed by the following formula (2): 1 / Tg=Σ(Wm / Tgm) / 100 (2) (wherein Wm is the content (mass%) of monomer m in the monomer components constituting the polymer, and Tgm is the glass transition temperature (absolute temperature: K) of the homopolymer of monomer m. The glass transition temperature of a polymer (non-volatile content) is calculated based on the following formula (3): 1 / Tg=W １ / Tg １ +W ２ / Tg ２ +W ３ / Tg ３ +...+W ｎ / Tg ｎ (3) [Where Tg is the glass transition temperature of the desired polymer (K), W １ , W ２ , W ３ ....W ｎ are the mass fractions of each monomer, and Tg １ , Tg ２ , Tg ３ ....Tg ｎindicates the glass transition temperature (K) of a homopolymer composed of monomers corresponding to the mass fraction of each monomer. In this specification, the glass transition temperature of a polymer means the glass transition temperature calculated based on formula (3). For a monomer whose glass transition temperature is unknown, the glass transition temperature is calculated using only monomers whose glass transition temperatures are known. The composition of the radical polymerizable monomers used as raw materials for the polymer can be determined taking the glass transition temperature of the polymer into consideration. The glass transition temperatures of homopolymers are, for example, 105°C for a homopolymer of methyl methacrylate, 8°C for a homopolymer of methyl acrylate, −20°C for a homopolymer of ethyl acrylate, −56°C for a homopolymer of n-butyl acrylate, 20°C for a homopolymer of n-butyl methacrylate, −80°C for a homopolymer of n-octyl acrylate, −58°C for a homopolymer of isooctyl acrylate, −70°C for a homopolymer of 2-ethylhexyl acrylate, and 20°C for a homopolymer of cyclohexyl acrylate. The glass transition temperature for a homopolymer of hexyl acrylate is 16°C, for a homopolymer of cyclohexyl methacrylate is 83°C, for a homopolymer of 2-hydroxyethyl acrylate is -15°C, for a homopolymer of 2-hydroxyethyl methacrylate is 55°C, for a homopolymer of 4-hydroxybutyl acrylate is -40°C, for a homopolymer of acrylic acid is 106°C, for a homopolymer of methacrylic acid is 105°C, for a homopolymer of styrene is 80°C, and for a homopolymer of N-vinylpyrrolidone is 170°C. The glass transition temperature of a (meth)acrylic polymer means a temperature determined based on the above-mentioned method for measuring the glass transition temperature of a polymer. The glass transition temperature of a (meth)acrylic polymer can be easily adjusted by appropriately adjusting the type and amount of the (meth)acrylic monomer that is a raw material for the (meth)acrylic polymer.

[0083] The weight-average molecular weight of the (meth)acrylic polymer is not particularly limited, but is preferably 10,000 to 1,500,000, more preferably 20,000 to 1,000,000, even more preferably 30,000 to 500,000, and even more preferably 50,000 to 300,000. In one embodiment, the weight-average molecular weight of the (meth)acrylic polymer may be 100,000 or more, or 150,000 or more. In this specification, the weight-average molecular weight of the (meth)acrylic polymer is a value measured using a gel permeation chromatography (GPC) measuring apparatus manufactured by Tosoh Corporation, product number: HLC-8220GPC, and a separation column manufactured by Tosoh Corporation, product number: TSKgel Super HZM-M, converted into a standard polystyrene (manufactured by Tosoh Corporation).

[0084] (Inorganic Particles) The two-component resin composition of the present invention preferably contains inorganic particles, and at least one of the above-mentioned Liquid A and the below-described Liquid B preferably contains inorganic particles. This can improve the thermal conductivity of the cured product. The inorganic particles are not particularly limited, but examples thereof include alkali metal carbonate particles such as sodium carbonate particles, sodium bicarbonate particles, potassium carbonate particles, and potassium bicarbonate particles; alkaline earth metal carbonate particles such as magnesium carbonate particles, calcium carbonate particles, and barium carbonate particles; carbonate particles such as ammonium carbonate particles and ammonium bicarbonate particles, zinc oxide particles, aluminum oxide particles, magnesium oxide particles, beryllium oxide particles, calcium oxide particles, zirconium oxide particles, aluminum oxide (alumina) particles, titanium dioxide particles, silica particles, magnesium hydroxide particles, aluminum hydroxide particles, calcium silicate particles, aluminum silicate particles, silicon carbide particles, silicon nitride particles, boron nitride particles, calcium sulfate particles, barium sulfate particles, magnesium carbonate particles, glass particles, kaolin, talc, mica powder, metal particles, and carbon black particles. These inorganic particles may be used alone or in combination of two or more kinds. Among these, aluminum oxide (alumina) particles are preferred.

[0085] The average particle size of the inorganic particles is preferably 0.3 μm or more from the viewpoint of preventing aggregation of the inorganic particles. It is more preferably 0.5 μm or more, and even more preferably 1 μm or more. Furthermore, from the viewpoint of improving the dispersion stability of the inorganic particles, the average particle size is preferably 100 μm or less. It is more preferably 80 μm or less, and even more preferably 50 μm or less. Therefore, the average particle size of the inorganic particles is preferably 0.3 to 100 μm, more preferably 0.5 to 80 μm, and even more preferably 1 to 50 μm. The average particle size of the inorganic particles refers to the volume average particle size measured using a particle size distribution measuring device (manufactured by Beckman Coulter, Inc., product number: LS13320) using a laser diffraction scattering method.

[0086] <Solution B> The solution B is characterized by containing an initiator.

[0087] (Initiator) The initiator is not particularly limited as long as it can initiate the polymerization reaction of the polymerizable monomer, and examples thereof include ketone peroxide-based polymerization initiators, hydroperoxide-based polymerization initiators, diacyl peroxide-based polymerization initiators, peroxyester-based polymerization initiators, peroxyketal-based polymerization initiators, dialkyl peroxide-based polymerization initiators, and peroxydicarbonate-based polymerization initiators. These polymerization initiators may be used alone or in combination of two or more. Preferred initiators are hydroperoxide-based polymerization initiators, diacyl peroxide-based polymerization initiators, and peroxyester-based polymerization initiators.

[0088] Examples of the ketone peroxide polymerization initiator include methyl ethyl ketone peroxide, cyclohexane peroxide, methylcyclohexane peroxide, methylacetoacetate peroxide, and acetylacetone peroxide.

[0089] Examples of the hydroperoxide polymerization initiator include p-menthane hydroperoxide, diisopropylbenzene hydroperoxide, 1,1,3,3-tetramethylbutyl hydroperoxide, cumene hydroperoxide, tert-hexyl hydroperoxide, tert-butyl hydroperoxide, etc. Among these, cumene hydroperoxide and tert-butyl hydroperoxide are preferred.

[0090] Examples of the diacyl peroxide polymerization initiator include diisobutyl peroxide, di-3,5,5-trimethylhexanoyl peroxide, octanoyl peroxide, dilauroyl peroxide, distearoyl peroxide, disuccinic acid peroxide, m-toluoyl peroxide, m-benzoyl peroxide, benzoyl peroxide, etc. Among these, m-benzoyl peroxide and benzoyl peroxide are preferred. Examples of the peroxy ester polymerization initiator include t-butyl peroxybenzoate, t-hexyl peroxypivalate, t-butyl peroxypivalate, 2,5-dimethyl-2,5-di(2-ethylhexanoylperoxy)hexane, 1,1,3,3-tetramethylbutylperoxy-2-ethylhexanoate, t-hexylperoxy-2-ethylhexanoate, t-butylperoxy-2-ethylhexanoate, t-butyl peroxylaurate, t-butylperoxy-3,5,5-trimethylhexanoate, t-hexylperoxyisopropyl monocarbonate, t-butylperoxyisopropyl monocarbonate, and t-butylperoxy-2-ethylhexyl monocarbonate. Of these, t-butyl peroxybenzoate is preferred. Examples of the peroxyketal polymerization initiator include 1,1-di(t-hexylperoxy)cyclohexane, 1,1-di(t-butylperoxy)cyclohexane, n-butyl-4,4-di(t-butylperoxy)valerate, 2,2-di(tert-butylperoxy)butane, etc. Examples of the dialkyl peroxide polymerization initiator include dicumyl peroxide, α,α'-di(tert-butylperoxy)diisopropylbenzene, tert-butylcumyl peroxide, di-tert-butyl peroxide, di-t-hexyl peroxide, 2,5-dimethyl-2,5-di(tert-butylperoxy)hexane, 2,5-dimethyl-2,5-bis(tert-butylperoxy)hexane-3, etc.Examples of the peroxydicarbonate polymerization initiator include diperoxydicarbonate polymerization initiators such as diisopropyl peroxydicarbonate and di-n-propyl peroxydicarbonate.

[0091] (Reaction Acceleration Aid) The solution B preferably contains a reaction acceleration aid. The reaction acceleration aid preferably contains a diketone compound. The diketone compound may be any compound having two carbonyl groups, and is preferably a compound represented by the following formula (4):

[0092]

[0093] (In the formula, R ５ , R ６ , R ７ are the same or different and represent an organic group. ５ and R ６ and / or R ６ and R ７ may be bonded to each other to form a ring structure. ) is preferred. Examples of the organic group include hydrocarbons which may have heteroatoms, amino groups, carboxyl groups, thiol groups, cyano groups, and halogen groups. The number of carbon atoms in the hydrocarbons which may have heteroatoms is not particularly limited, but is preferably 1 to 20. It is more preferably 1 to 15, even more preferably 1 to 10, even more preferably 1 to 8, and particularly preferably 1 to 6.

[0094] The hydrocarbon may have a heteroatom, and may have a substituent having a heteroatom, such as an amino group, a carboxyl group, a thiol group, a cyano group, a halogen group, a hydroxyl group, an ether group, an ester group, or a thioether group.

[0095] Examples of the hydrocarbon group include an alkyl group, an alkenyl group, an alkynyl group, an aryl group, an aralkyl group, and a group obtained by abstracting a hydrogen atom from a heterocyclic compound.

[0096] Examples of the alkyl group include the above-mentioned alkyl groups having 4 to 15 carbon atoms, aliphatic alkyl groups such as methyl, ethyl, propyl, isopropyl, hexadecyl, heptadecyl, stearyl, and icosyl groups, and alicyclic alkyl groups such as cyclopropyl groups.

[0097] Examples of the alkenyl group include the above-mentioned alkenyl groups having 4 to 15 carbon atoms, vinyl groups, allyl groups, hexadecenyl groups, heptadecenyl groups, octadecenyl groups, and icosinyl groups.

[0098] Examples of the alkynyl group and the aryl group include the above-mentioned alkynyl group having 4 to 15 carbon atoms, the above-mentioned aryl group having 6 to 15 carbon atoms, and the above-mentioned aralkyl group having 6 to 15 carbon atoms.

[0099] Examples of the heterocyclic compound include imidazole, imidazolidine, pyrazole, benzimidazole, pyridine, pyrimidine, pyrazine, pyridazine, pyrrole, pyrroline, thiophene, furan, benzothiophene, benzofuran, indole, dibenzothiophene, dibenzofuran, carbazole, thiazole, benzothiazole, oxazole, benzoxazole, quinoline, isoquinoline, quinoxaline, benzothiadiazole, phenanthridine, oxadiazole, and thiadiazole.

[0100] The above R ５ As the R, an alkyl group having 1 to 3 carbon atoms, an alkoxy group having 1 to 3 carbon atoms, and a phenyl group are preferred. A methyl group, an ethyl group, a methoxy group, an ethoxy group, and a phenyl group are more preferred, and a methyl group is even more preferred. ６ , R ７ is preferably an alkyl group having 1 to 3 carbon atoms, an alkoxy group having 1 to 3 carbon atoms, a phenyl group, R ６ and R ７ are bonded to form a ring structure having 3 to 8 carbon atoms. ６ and R ７ are bonded to form a lactone structure having 3 to 8 carbon atoms. The lactone structure preferably has 3 to 7 carbon atoms, more preferably 3 to 6 carbon atoms, and even more preferably 3 to 5 carbon atoms.

[0101] Specific examples of the diketone compound include α-acetyl-γ-butyrolactone, ethyl cyclopentanone-2-carboxylate, methyl cyclopentanone-2-carboxylate, acetylacetone, methyl acetoacetate, ethyl acetoacetate, n-butyl acetoacetate, isopropyl acetoacetate, allyl ether acetoacetate, diethyl 1,1-cyclopropanedicarboxylate, dimethyl malonate, diethyl malonate, dipropyl malonate, diisopropyl malonate, tert-butylethyl malonate, dimethyl methylmalonate, diethyl ethylmalonate, 1,3-diphenyl-1,3-propanedione, acetoacetamide, N-methyl methyl malonate, diethyl ... diethyl ethyl malonate, 1,3 Examples of the acetoacetamide include acetoacetamide, N,N-dimethylacetoacetamide, N,N-diethylacetoacetamide, N,N-diisopropylacetoacetamide, N,N-dibutylacetoacetamide, N,N-dihydroxyethylacetoacetamide, N-methylacetoacetanilide, 1-acetoacetylpyrrolidine, 1-acetoacetylindole, 1-acetoacetylimidazole, 1-acetoacetylpyrrole, 1-acetoacetylimidazoline, 1-acetoacetylpyrroline, 1-acetoacetylimidazolidine, 1-acetoacetylpiperidine, 1-acetoacetylpiperazine, and N-pyrrolidininoacetoacetamide. Preferred are α-acetyl-γ-butyrolactone, dimethyl malonate, diethyl malonate, ethyl cyclopentanone-2-carboxylate, and 1,3-diphenyl-1,3-propanedione, and more preferred is α-acetyl-γ-butyrolactone.

[0102] ((Meth)acrylic polymer) The above-mentioned liquid B preferably contains a (meth)acrylic polymer. This allows the inorganic particles to be dispersed more thoroughly. An embodiment in which the above-mentioned liquids A and B contain a (meth)acrylic polymer is one of the preferred embodiments of the present invention. When the above-mentioned liquids A and B contain a (meth)acrylic polymer, the (meth)acrylic polymers contained in each may be the same or different. For example, an embodiment in which one of the liquids A and B contains a (meth)acrylic polymer having a weight-average molecular weight of 10,000 to 150,000, and the other contains a (meth)acrylic polymer having a weight-average molecular weight of 150,000 to 1,500,000 is one of the preferred embodiments of the present invention.

[0103] (Inorganic particles) The liquid B may contain inorganic particles. Specific examples and preferred examples of the inorganic particles are as described for the liquid A. An embodiment in which the liquid A and the liquid B contain inorganic particles is one of the preferred embodiments of the present invention. When the liquid A and the liquid B contain inorganic particles, the inorganic particles contained in each may be the same or different.

[0104] The above-mentioned Solution A and / or Solution B may each contain other additives to the extent that the object of the present invention is not impaired. Examples of other additives include colorants such as pigments, leveling agents, UV absorbers, UV stabilizers, antioxidants, polymerization inhibitors, fillers, coupling agents, rust inhibitors, antibacterial agents, metal deactivators, wetting agents, antifoaming agents, surfactants, reinforcing agents, plasticizers, lubricants, antifogging agents, anticorrosion agents, pigment dispersants, flow control agents, peroxide decomposers, mold decolorizing agents, fluorescent brighteners, organic flame retardants, inorganic flame retardants, anti-dripping agents, melt flow modifiers, antistatic agents, anti-algae agents, anti-fungal agents, flame retardants, slip agents, metal chelating agents, anti-blocking agents, heat stabilizers, processing stabilizers, dispersants, thickeners, rheology control agents, foaming agents, antioxidants, preservatives, antistatic agents, silane coupling agents, antioxidants, and film-forming aids, but the present invention is not limited to these examples. These additives may be used alone or in combination of two or more kinds.

[0105] The methods for preparing the above-mentioned solutions A and B are not particularly limited, and they can be prepared by mixing the essential components and optional components, respectively, using means such as a batch mixer, a tumbler, a Henschel mixer, a Banbury mixer, a roll, a kneader, a single-screw extruder, or a twin-screw extruder. The temperature at which the above-mentioned components are mixed is not particularly limited, and may be room temperature, a temperature higher than room temperature, or a temperature lower than room temperature. The atmosphere at which the above-mentioned components are mixed is not particularly limited, and may be air, but from the viewpoint of avoiding the influence of oxygen gas contained in the air, it may also be an inert gas such as nitrogen gas or argon gas.

[0106] [Two-component resin composition] The two-component resin composition of the present invention comprises the thus obtained components A and B. The ratio of components A to B is preferably adjusted so that the components contained in components A and B are in the preferred ratio described above.

[0107] Furthermore, the amount of Liquid A excluding the inorganic particles per 100 parts by mass of Liquid B is preferably about 3 to 300 parts by mass, taking into consideration the convenience of mixing Liquid A and Liquid B. In the present invention, when Liquid A and Liquid B are mixed, they react quickly even at room temperature, and therefore it is not necessary to produce a cured product such as a heat dissipating material by heating as in the conventional method, and therefore it is possible to efficiently produce a cured product such as a heat dissipating material on a production line in a factory, for example.

[0108] A stirring device can be used when mixing liquid A and liquid B. Examples of stirring devices include batch mixers, tumblers, Henschel mixers, Banbury mixers, rolls, kneaders, single-screw extruders, and twin-screw extruders, but the present invention is not limited to these examples. The temperature when mixing liquid A and liquid B is not particularly limited, but room temperature is preferable from the viewpoint of efficiently producing cured products such as heat dissipation materials without using devices such as heating and cooling devices. Here, room temperature cannot be determined in general because it varies depending on the region, but it is usually 0 to 40°C, preferably 0 to 35°C, and more preferably 1 to 30°C. Furthermore, the temperature when mixing liquid A and liquid B may be a temperature above room temperature or a temperature below room temperature as necessary, but from the viewpoint of efficiently producing cured products such as heat dissipation materials, a temperature of about 0 to 50°C is preferable. Furthermore, the atmosphere when mixing liquid A and liquid B is not particularly limited and may be air, but may also be an inert gas such as nitrogen gas or argon gas from the viewpoint of avoiding the effects of oxygen gas contained in the air.

[0109] When liquid A and liquid B are mixed, curing of the resulting mixture begins and typically completes within about 30 to 90 minutes at room temperature. The end point of curing of the mixture can be the tack-free time of the surface of the cured product obtained from the mixture. Tack-free time refers to the time from the time liquid A and liquid B are mixed until the components of the cured product no longer adhere to the surface of a human finger that has been degreased with ethanol or the like. By mixing liquid A and liquid B contained in the two-component resin composition of the present invention in this manner, liquid A and liquid B react to produce a cured product such as a heat dissipation material.

[0110] The two-component resin composition of the present invention can be suitably used as a resin, adhesive, pressure-sensitive adhesive, etc. for heat dissipation materials. The present invention also relates to the use of the two-component resin composition of the present invention as a resin, adhesive, or pressure-sensitive adhesive for heat dissipation materials. The present invention also relates to a heat dissipation material obtained by curing the two-component resin composition. The present invention also relates to a method for producing a heat dissipation material, which includes a step of curing the two-component resin composition of the present invention. There are no particular limitations on the shape of the heat dissipation material obtained using the two-component resin composition of the present invention. Examples of the shape of the heat dissipation material include a sheet (film), tape, cylinder, or desired molded product shape, but the present invention is not limited to these shapes. Sheet- or tape-shaped heat dissipating materials can be produced by, for example, mixing liquid A and liquid B, forming a coating on a substrate with the resulting mixture using, for example, a brush, bar coater, applicator, air spray, airless spray, roll coater, or flow coater, and then curing the resulting coating; or by mixing liquid A and liquid B, extruding the resulting mixture from an extrusion molding machine through a T-die to form a sheet or film, and then curing the resulting mixture. Cylindrical heat dissipating materials can be produced by, for example, mixing liquid A and liquid B, extruding the resulting mixture from an extrusion molding machine through a spider to form a cylindrical heat dissipating material, and then curing the material. Heat dissipating materials having the desired molded shape can be produced by, for example, mixing liquid A and liquid B, and molding the resulting mixture into the desired shape using an injection molding machine or the like.

[0111] The thermal conductivity of the heat dissipation material can be adjusted, for example, by adjusting the amount of inorganic particles used as the thermally conductive material. The thermal conductivity of the heat dissipation material is not particularly limited, but from the viewpoint of improving the heat dissipation performance of the heat dissipation material, it is preferably 0.5 W / m K or more, and more preferably 1 W / m K or more. The thermal conductivity of the heat dissipation material is a value measured at a temperature of 25°C using a rapid thermal conductivity meter (product number: QTM-500) manufactured by Kyoto Electronics Manufacturing Co., Ltd.

[0112] The present invention will be described in more detail below with reference to examples, but the present invention is not limited to these examples. Unless otherwise specified, "parts" means "parts by weight" and "%" means "% by mass."

[0113] [Monomer Conversion Rate] Liquids A and B were mixed in the atmosphere at 25°C and allowed to stand for 24 hours, and 1 g of the cured product formed by curing was cut out, and 9 g of ethyl acetate and 0.03 g of tridecane as an internal standard were added. The solution was heated at 50°C for 2 hours with stirring, and the monofunctional monomer conversion rate was measured by GC (gas chromatography). The monomer conversion rate was evaluated based on the following evaluation criteria. The monomer conversion rate was measured under the following conditions using a GC-2014 gas chromatograph (GC) manufactured by Shimadzu Corporation. - Temperature increase conditions: hold at 40°C for 5 minutes ⇒ increase temperature from 40°C to 230°C at a rate of 15°C / min ⇒ hold at 230°C for 10 minutes - Column: G-100 (length: 20.0 m, film thickness: 1.00 μm) - Carrier gas: N2 - Carrier gas flow rate: 20.0 mL / min - Vaporization chamber temperature: 230°C - Detector: FID - Detector temperature: 230°C (Evaluation criteria) ○: Monofunctional monomer conversion rate is 97% or more. △: Monofunctional monomer conversion rate is 90% or more and less than 97%. ×: Monofunctional monomer conversion rate is less than 90%.

[0114] [Pot life] The time from when liquid A and liquid B were mixed in the atmosphere at 25°C until the viscosity doubled was measured. (Evaluation criteria) ◯: Pot life was 2 hours or more. Δ: Pot life was 30 minutes or more but less than 2 hours. ×: Pot life was less than 30 minutes.

[0115] [Curability] A resin composition prepared by mixing liquids A and B was allowed to stand in the air at 25°C, and the surface of the resulting cured product was touched with the fingers of a person whose fingers had been degreased with ethanol. The time from immediately after mixing until the composition no longer adhered to the surface (tack-free time) was measured, and curability was evaluated based on the following evaluation criteria. (Evaluation criteria) ◯: Tack-free time was 6 hours or more but less than 72 hours. Δ: Tack-free time was 2 hours or more but less than 6 hours. ×1: Tack-free time was less than 2 hours. ×2: Not tack-free even after 72 hours or more had passed.

[0116] [Hardness] From the time when liquids A and B were mixed in the atmosphere at 25°C, the mixed liquid obtained by mixing liquids A and B was left to stand for 24 hours with a PET film covering it to prevent contact with the atmosphere, and the hardness of the cured product formed by curing was measured within 1 second using a durometer (OO type durometer (rubber hardness meter, manufactured by Teclock Corporation)) in accordance with ASTM D 2240. The sample had a width of 100 mm, a depth of 10 mm, and a thickness of 6 mm, and the measurement was carried out at room temperature. The obtained hardness was calculated by averaging the values ​​measured at 10 locations, and the hardness was evaluated based on the following evaluation criteria: (Evaluation criteria) 〇1: Hardness is 55 or more and less than 80. 〇2: Hardness is 30 or more and less than 55. ×1: Hardness is 80 or more. ×2: Hardness is less than 30.

[0117] Example 1 Preparation of Solution A 14 g of 2-ethylhexyl acrylate / 2-hydroxyethyl acrylate copolymer (2-ethylhexyl acrylate / 2-hydroxyethyl acrylate (mass ratio) = 95 / 5, weight average molecular weight: 200,000, glass transition temperature: approximately -68°C) as a (meth)acrylic polymer, 33.3 g of trimellitic acid triester plasticizer (manufactured by ADEKA Corporation, trade name: Adeka Cizer C-880), 45 g of 2-ethylhexyl acrylate, 5 g of styrene, naphthalene, methyl methacrylate, methyl ... 1.2 g of cobalt phthenate (manufactured by Tokyo Chemical Industry Co., Ltd., containing approximately 8% cobalt) and 1.5 g of tris(2-acryloyloxyethyl) isocyanurate (manufactured by Toagosei Co., Ltd., trade name: M-313) as a crosslinking agent were mixed at room temperature (approximately 25°C) in the air until a uniform composition was obtained, to prepare liquid A. Further, 733 g of alumina powder (average particle size: 10 μm) was added to liquid A, and the mixture obtained by mixing until a uniform composition was obtained was used as liquid A. [Preparation of liquid B] 26 g of 2-ethylhexyl acrylate / 2-hydroxyethyl acrylate copolymer (2-ethylhexyl acrylate / 2-hydroxyethyl acrylate (mass ratio) = 95 / 5, weight average molecular weight: 50,000, glass transition temperature: approximately -68°C) as a (meth)acrylic polymer, 65 g of trimellitic acid triester plasticizer (manufactured by ADEKA Corporation, trade name: Adeka Cizer C-880), α-acetyl-γ-butyrolactone (manufactured by Tokyo Chemical Industry Co., Ltd.) as a reaction accelerator, Liquid B was prepared by mixing 5 g of alumina powder (manufactured by Seiseki Kogyo Co., Ltd.) and 4 g of a peroxide initiator (a mixture of tert-butyl peroxybenzoate and cumene hydroperoxide) (manufactured by Kayaku Nouryon Co., Ltd., product name: 328E) as a polymerization initiator in air at room temperature (approximately 25°C) until a uniform composition was obtained. 733 g of alumina powder (average particle size: 10 μm) was added to Liquid B, and the mixture was mixed until a uniform composition was obtained, and this mixture was used as Liquid B. Next, a two-part curable composition (two-part resin composition) was prepared using Liquid A and Liquid B obtained above, and its physical properties were examined as described above. The results are shown in Table 1.

[0118] Example 2 Preparation of Solution A 14 g of 2-ethylhexyl acrylate / 2-hydroxyethyl acrylate copolymer (2-ethylhexyl acrylate / 2-hydroxyethyl acrylate (mass ratio) = 95 / 5, weight average molecular weight: 200,000, glass transition temperature: approximately -68°C) as a (meth)acrylic polymer, 33.3 g of trimellitic acid triester plasticizer (manufactured by ADEKA Corporation, trade name: Adeka Cizer C-880), 40 g of 2-octyl acrylate, and vinyl toluene (manufactured by Tokyo Chemical Industry Co., Ltd.) were used. ], 1.2 g of cobalt naphthenate [manufactured by Tokyo Chemical Industry Co., Ltd., containing approximately 8% cobalt], and 1.5 g of tris(2-acryloyloxyethyl) isocyanurate [manufactured by Toagosei Co., Ltd., product name: M-313] as a crosslinking agent were mixed at room temperature (approximately 25°C) in the air until a uniform composition was obtained, to prepare liquid A, and 733 g of alumina powder (average particle size: 10 μm) was added to liquid A and mixed until a uniform composition was obtained, and the resulting mixture was used as liquid A. [Preparation of Solution B] Solution B was prepared by mixing 26 g of a 2-ethylhexyl acrylate / 2-hydroxyethyl acrylate copolymer (2-ethylhexyl acrylate / 2-hydroxyethyl acrylate (mass ratio) = 95 / 5, weight average molecular weight: 50,000, glass transition temperature: approximately −68° C.) as a (meth)acrylic polymer, 67 g of a trimellitic acid triester plasticizer (manufactured by ADEKA Corporation, trade name: Adeka Cizer C-880), 5 g of α-acetyl-γ-butyrolactone (manufactured by Tokyo Chemical Industry Co., Ltd.) as a reaction accelerator, and 2 g of a peroxide initiator (manufactured by NOF Corporation, trade name: Perbutyl Z) as a polymerization initiator at room temperature (approximately 25° C.) in the air until a uniform composition was obtained. 733 g of alumina powder (average particle size: 10 μm) was then added to Solution B, and the mixture obtained by mixing until a uniform composition was obtained was used as Solution B. Next, a two-component curable composition was prepared using the above-obtained liquids A and B, and the physical properties were examined in the same manner as in Example 1. The results are shown in Table 1.

[0119] Example 3 Preparation of Solution A 14 g of 2-ethylhexyl acrylate / 2-hydroxyethyl acrylate copolymer (2-ethylhexyl acrylate / 2-hydroxyethyl acrylate (mass ratio) = 95 / 5, weight average molecular weight: 200,000, glass transition temperature: approximately -68°C) as a (meth)acrylic polymer, 33.3 g of trimellitic acid triester plasticizer (manufactured by ADEKA Corporation, trade name: Adeka Cizer C-880), 45 g of 2-ethylhexyl acrylate, α-methylstyrene [Tokyo Chemical Industry Co., Ltd. Liquid A was prepared by mixing 5 g of cobalt naphthenate (manufactured by Tokyo Chemical Industry Co., Ltd., containing approximately 8% cobalt), 1.2 g of cobalt naphthenate, and 1.5 g of tris(2-acryloyloxyethyl) isocyanurate (manufactured by Toagosei Co., Ltd., product name: M-313) as a crosslinking agent at room temperature (approximately 25°C) in the air until a uniform composition was obtained. Further, 733 g of alumina powder (average particle size: 10 μm) was added to Liquid A, and the mixture was mixed until a uniform composition was obtained, and the resulting mixture was used as Liquid A. [Preparation of Solution B] Solution B was prepared by mixing 26 g of a 2-ethylhexyl acrylate / 2-hydroxyethyl acrylate copolymer (2-ethylhexyl acrylate / 2-hydroxyethyl acrylate (mass ratio) = 95 / 5, weight average molecular weight: 50,000, glass transition temperature: approximately −68° C.) as a (meth)acrylic polymer, 67 g of a trimellitic acid triester plasticizer (manufactured by ADEKA Corporation, trade name: Adeka Cizer C-880), 5 g of α-acetyl-γ-butyrolactone (manufactured by Tokyo Chemical Industry Co., Ltd.) as a reaction accelerator, and 2 g of a peroxide initiator (manufactured by NOF Corporation, trade name: Perbutyl Z) as a polymerization initiator at room temperature (approximately 25° C.) in the air until a uniform composition was obtained. 733 g of alumina powder (average particle size: 10 μm) was then added to Solution B, and the mixture obtained by mixing until a uniform composition was obtained was used as Solution B. Next, a two-component curable composition was prepared using the above-obtained liquids A and B, and the physical properties were examined in the same manner as in Example 1. The results are shown in Table 1.

[0120] Example 4 Preparation of Solution A 14 g of 2-ethylhexyl acrylate / 2-hydroxyethyl acrylate copolymer (2-ethylhexyl acrylate / 2-hydroxyethyl acrylate (mass ratio) = 95 / 5, weight average molecular weight: 200,000, glass transition temperature: approximately -68°C) as a (meth)acrylic polymer, 33.3 g of trimellitic acid triester plasticizer (manufactured by ADEKA Corporation, trade name: Adeka Cizer C-880), 25 g of 2-ethylhexyl acrylate, 25 g of styrene, naphthalene, 1 g of methyl acrylate ... Liquid A was prepared by mixing 1.2 g of cobalt phthenate (manufactured by Tokyo Chemical Industry Co., Ltd., containing approximately 8% cobalt) and 1.5 g of tris(2-acryloyloxyethyl) isocyanurate (manufactured by Toagosei Co., Ltd., product name: M-313) as a crosslinking agent at room temperature (approximately 25°C) in the air until a uniform composition was obtained. Further, 733 g of alumina powder (average particle size: 10 μm) was added to Liquid A, and the mixture obtained by mixing until a uniform composition was obtained was used as Liquid A. [Preparation of Solution B] Solution B was prepared by mixing 26 g of a 2-ethylhexyl acrylate / 2-hydroxyethyl acrylate copolymer (2-ethylhexyl acrylate / 2-hydroxyethyl acrylate (mass ratio) = 95 / 5, weight average molecular weight: 50,000, glass transition temperature: approximately −68° C.) as a (meth)acrylic polymer, 67 g of a trimellitic acid triester plasticizer (manufactured by ADEKA Corporation, trade name: Adeka Cizer C-880), 5 g of α-acetyl-γ-butyrolactone (manufactured by Tokyo Chemical Industry Co., Ltd.) as a reaction accelerator, and 2 g of a peroxide initiator (manufactured by NOF Corporation, trade name: Perbutyl Z) as a polymerization initiator at room temperature (approximately 25° C.) in the air until a uniform composition was obtained. 733 g of alumina powder (average particle size: 10 μm) was then added to Solution B, and the mixture obtained by mixing until a uniform composition was obtained was used as Solution B. Next, a two-component curable composition was prepared using the above-obtained liquids A and B, and the physical properties were examined in the same manner as in Example 1. The results are shown in Table 1.

[0121] Comparative Example 1 Preparation of Solution A 14 g of 2-ethylhexyl acrylate / 2-hydroxyethyl acrylate copolymer as a (meth)acrylic polymer [2-ethylhexyl acrylate / 2-hydroxyethyl acrylate (mass ratio) = 95 / 5, weight average molecular weight: 200,000, glass transition temperature: approximately -68°C], 33.3 g of trimellitic acid triester plasticizer [manufactured by ADEKA Corporation, trade name: Adeka Cizer C-880], 12.5 g of 2-ethylhexyl acrylate, and 37.5 g of styrene 1.2 g of cobalt naphthenate (manufactured by Tokyo Chemical Industry Co., Ltd., containing approximately 8% cobalt), and 1.5 g of tris(2-acryloyloxyethyl) isocyanurate (manufactured by Toagosei Co., Ltd., product name: M-313) as a crosslinking agent were mixed at room temperature (approximately 25°C) in the air until a uniform composition was obtained, to prepare liquid A. Further, 733 g of alumina powder (average particle size: 10 μm) was added to liquid A, and the mixture was mixed until a uniform composition was obtained, and the resulting mixture was used as liquid A. [Preparation of Solution B] Solution B was prepared by mixing 26 g of a 2-ethylhexyl acrylate / 2-hydroxyethyl acrylate copolymer (2-ethylhexyl acrylate / 2-hydroxyethyl acrylate (mass ratio) = 95 / 5, weight average molecular weight: 50,000, glass transition temperature: approximately −68° C.) as a (meth)acrylic polymer, 67 g of a trimellitic acid triester plasticizer (manufactured by ADEKA Corporation, trade name: Adeka Cizer C-880), 5 g of α-acetyl-γ-butyrolactone (manufactured by Tokyo Chemical Industry Co., Ltd.) as a reaction accelerator, and 2 g of a peroxide initiator (manufactured by NOF Corporation, trade name: Perbutyl Z) as a polymerization initiator at room temperature (approximately 25° C.) in the air until a uniform composition was obtained. 733 g of alumina powder (average particle size: 10 μm) was then added to Solution B, and the mixture obtained by mixing until a uniform composition was obtained was used as Solution B. Next, a two-component curable composition was prepared using the above-obtained liquids A and B, and the physical properties were examined in the same manner as in Example 1. The results are shown in Table 1.

[0122] Comparative Example 2 [Preparation of Solution A] 14 g of 2-ethylhexyl acrylate / 2-hydroxyethyl acrylate copolymer (2-ethylhexyl acrylate / 2-hydroxyethyl acrylate (mass ratio) = 95 / 5, weight average molecular weight: 200,000, glass transition temperature: approximately -68°C) as a (meth)acrylic polymer, 33.3 g of trimellitic acid triester plasticizer (manufactured by ADEKA Corporation, trade name: Adeka Cizer C-880), 50 g of styrene, 10 g of cobalt naphthenate [ Liquid A was prepared by mixing 1.2 g of tris(2-acryloyloxyethyl) isocyanurate (manufactured by Tokyo Chemical Industry Co., Ltd., containing approximately 8% cobalt) and 1.5 g of a crosslinking agent, tris(2-acryloyloxyethyl) isocyanurate (manufactured by Toagosei Co., Ltd., product name: M-313), at room temperature (approximately 25°C) in the air until a uniform composition was obtained. Further, 733 g of alumina powder (average particle size: 10 μm) was added to Liquid A, and the mixture obtained by mixing until a uniform composition was obtained was used as Liquid A. [Preparation of Solution B] Solution B was prepared by mixing 26 g of a 2-ethylhexyl acrylate / 2-hydroxyethyl acrylate copolymer (2-ethylhexyl acrylate / 2-hydroxyethyl acrylate (mass ratio) = 95 / 5, weight average molecular weight: 50,000, glass transition temperature: approximately −68° C.) as a (meth)acrylic polymer, 67 g of a trimellitic acid triester plasticizer (manufactured by ADEKA Corporation, trade name: Adeka Cizer C-880), 5 g of α-acetyl-γ-butyrolactone (manufactured by Tokyo Chemical Industry Co., Ltd.) as a reaction accelerator, and 2 g of a peroxide initiator (manufactured by NOF Corporation, trade name: Perbutyl Z) as a polymerization initiator at room temperature (approximately 25° C.) in the air until a uniform composition was obtained. 733 g of alumina powder (average particle size: 10 μm) was then added to Solution B, and the mixture obtained by mixing until a uniform composition was obtained was used as Solution B. Next, a two-component curable composition was prepared using the above-obtained liquids A and B, and the physical properties were examined in the same manner as in Example 1. The results are shown in Table 1.

[0123] Comparative Example 3 Preparation of Solution A 14 g of 2-ethylhexyl acrylate / 2-hydroxyethyl acrylate copolymer (2-ethylhexyl acrylate / 2-hydroxyethyl acrylate (mass ratio) = 95 / 5, weight average molecular weight: 200,000, glass transition temperature: approximately -68°C) as a (meth)acrylic polymer, 33.3 g of trimellitic acid triester plasticizer (manufactured by ADEKA Corporation, trade name: Adeka Cizer C-880), 50 g of 2-ethylhexyl acrylate, and naphthenic acid were mixed together. 1.2 g of cobalt (manufactured by Tokyo Chemical Industry Co., Ltd., containing approximately 8% cobalt) and 1.5 g of tris(2-acryloyloxyethyl) isocyanurate (manufactured by Toagosei Co., Ltd., trade name: M-313) as a crosslinking agent were mixed at room temperature (approximately 25°C) in the air until a uniform composition was obtained, to prepare liquid A. 733 g of alumina powder (average particle size: 10 μm) was then added to liquid A, and the mixture obtained by mixing until a uniform composition was obtained was used as liquid A. [Preparation of liquid B] 26 g of 2-ethylhexyl acrylate / 2-hydroxyethyl acrylate copolymer (2-ethylhexyl acrylate / 2-hydroxyethyl acrylate (mass ratio) = 95 / 5, weight average molecular weight: 50,000, glass transition temperature: approximately -68°C) as a (meth)acrylic polymer, 65 g of trimellitic acid triester plasticizer (manufactured by ADEKA Corporation, trade name: Adeka Cizer C-880), α-acetyl-γ-butyrolactone (manufactured by Tokyo Chemical Industry Co., Ltd.) as a reaction accelerator, Liquid B was prepared by mixing 5 g of alumina powder (average particle size: 10 μm) and 4 g of a peroxide initiator (a mixture of tert-butyl peroxybenzoate and cumene hydroperoxide) (manufactured by Nouryon Chemical Industries Co., Ltd., product name: 328E) as a polymerization initiator at room temperature (approximately 25°C) in the air until a uniform composition was obtained. 733 g of alumina powder (average particle size: 10 μm) was added to Liquid B, and the mixture was mixed until a uniform composition was obtained, and this mixture was used as Liquid B. Next, a two-part curable composition was prepared using Liquid A and Liquid B obtained above, and its physical properties were examined in the same manner as in Example 1. The results are shown in Table 1.

[0124] Comparative Example 4 [Preparation of Solution A] 14 g of 2-ethylhexyl acrylate / 2-hydroxyethyl acrylate copolymer [2-ethylhexyl acrylate / 2-hydroxyethyl acrylate (mass ratio) = 95 / 5, weight average molecular weight: 200,000, glass transition temperature: approximately -68°C] as a (meth)acrylic polymer, 33.3 g of trimellitic acid triester plasticizer [manufactured by ADEKA Corporation, trade name: Adeka Cizer C-880], 50 g of 2-ethylhexyl acrylate, N, Liquid A was prepared by mixing 1.2 g of N-bis(2-hydroxyethyl)-p-toluidine and 1.5 g of tris(2-acryloyloxyethyl) isocyanurate (manufactured by Toagosei Co., Ltd., product name: M-313) as a crosslinking agent at room temperature (approximately 25°C) in the air until a uniform composition was obtained. Further, 733 g of alumina powder (average particle size: 10 μm) was added to Liquid A, and the mixture obtained by mixing until a uniform composition was obtained was used as Liquid A. [Preparation of Liquid B] 26 g of 2-ethylhexyl acrylate / 2-hydroxyethyl acrylate copolymer (2-ethylhexyl acrylate / 2-hydroxyethyl acrylate (mass ratio) = 95 / 5, weight average molecular weight: 50,000, glass transition temperature: approximately -68°C) as a (meth)acrylic polymer, 69 g of trimellitic acid triester plasticizer (manufactured by ADEKA Corporation, trade name: Adeka Cizer C-880), and 5 g of peroxide initiator (benzoyl peroxide) (manufactured by NOF Corporation, trade name: Niper NS) as a polymerization initiator were mixed at room temperature (approximately 25°C) in the air until a uniform composition was obtained, to prepare Liquid B. 733 g of alumina powder (average particle size: 10 μm) was added to Liquid B, and the mixture obtained by mixing until a uniform composition was obtained was used as Liquid B. Next, a two-part curable composition was prepared using the above-obtained Liquids A and B, and the physical properties were examined in the same manner as in Example 1. The results are shown in Table 1.

[0125]

Claims

1. A two-component resin composition consisting of liquid A and liquid B, The solution A contains a polymerizable monomer and a reaction accelerator, the polymerizable monomer comprises an aromatic vinyl monomer; the content of the aromatic vinyl monomer is more than 0% by mass and 60% by mass or less, based on 100% by mass of the polymerizable monomer; The component B is a two-component resin composition containing an initiator.

2. 2. The two-component resin composition according to claim 1, wherein the polymerizable monomer comprises a monomer having a glass transition temperature of −180 to −20° C. when homopolymerized.

3. 3. The two-component resin composition according to claim 1, wherein the polymerizable monomer comprises a (meth)acrylate having a hydrocarbon group having 4 to 15 carbon atoms, which may have a substituent.

4. The two-component resin composition according to claim 1 or 2, wherein a content ratio of the initiator relative to 100% by mass of the polymerizable monomer is 1.5% by mass or more.

5. The two-component resin composition according to claim 1 or 2, wherein the polymerizable monomer includes a monomer having two or more polymerizable unsaturated bonds.

6. The two-component resin composition according to claim 1 , wherein the reaction accelerator comprises a metal compound.

7. The solution B contains a reaction accelerator, The two-component resin composition according to claim 1 or 2, wherein the reaction accelerator comprises a diketone compound.

8. 3. The two-component resin composition according to claim 1, wherein the content of the polymerizable monomer is 40 to 99.9% by mass relative to 100% by mass of the total amount of Liquid A (excluding inorganic particles, if any, in Liquid A).

9. The two-component resin composition according to claim 1 or 2, wherein the liquid A and / or the liquid B contains a (meth)acrylic polymer.

10. The two-component resin composition according to claim 1 or 2, wherein the liquid A and / or the liquid B contains a plasticizer.

11. The two-component resin composition according to claim 1 or 2, wherein the liquid A and / or the liquid B contains inorganic particles.

12. The two-component resin composition according to claim 1 or 2, which is used for a heat dissipation material.