JP7076099B2 - Thermally conductive insulating elastomer composition, thermally conductive insulating elastomer molded product and its manufacturing method - Google Patents

Description

The present invention relates to a thermally conductive insulating elastomer composition, a thermally conductive insulating elastomer molded body, and a method for producing the same, which are useful as materials for members required for insulation and heat dissipation such as electronic circuit boards.

With the miniaturization and high integration of electrical and electronic devices, heat generation of mounted parts and high temperature of the usage environment have become remarkable, and there is an increasing demand for improving heat dissipation of constituent members. In particular, metals and ceramics with high thermal conductivity are currently used for heat dissipation members of automobile members and high-power LEDs, but in order to reduce weight, processability, and increase the degree of freedom in shape, high thermal conductivity is achieved. , And a heat conductive resin material having molding processability is required. In particular, a resin made of a polymer compound is an inexpensive insulating material having excellent moldability, and is therefore used in various electronic components such as a base material for an electronic circuit board, a motor insulating material, and an insulating adhesive. In recent years, as the density and output of these electronic components have increased, the amount of heat generated from the electronic components has increased. Therefore, there is a strong demand for measures to release the heat of electronic components.

To solve this problem, in the prior art, a method of filling the inside of a resin with a filler made of an inorganic substance such as alumina or silica to increase the thermal conductivity of the resin is used. For example, Patent Documents 1 and 2 propose a technique of adding an inorganic filler such as crystalline silica and aluminum oxide to a polymer resin to impart thermal conductivity. In this case, the continuum formed by connecting the inorganic fillers functions as a heat conduction path. That is, the inorganic fillers filled in the resin need to be in contact with each other, and it is necessary to fill a large amount of the inorganic fillers for efficient heat conduction. Further, the conventional heat conductive insulating resin molded product has the following technical problems because it is necessary to add a large amount of an inorganic filler. (1) The weight is heavy. (2) Since the inorganic filler is hard, it has poor workability. (3) Voids are likely to be generated at the interface between the inorganic filler and the resin, and water stays there, so that the moisture resistance is low. (4) Since the inorganic filler is expensive, the manufacturing cost is high. (5) A resin molded body having a large amount of inorganic filler filled requires a certain thickness in order to maintain its shape, and it is difficult to reduce the thickness. In order to solve these problems, in Patent Document 3, a core / shell particle comprising a core particle containing a polymer compound and a shell containing a thermally conductive and insulating inorganic compound covering the core particle. A thermally conductive insulating resin molded body molded by an aggregate has been proposed.

Japanese Unexamined Patent Publication No. 11-23649 Japanese Patent No. 3559137 Japanese Patent No. 5278488

However, the heat conductive insulating resin molded body described in Patent Document 3 has a problem that the heat conductivity is low because the core particles containing the polymer compound are coated with the shell containing the inorganic compound. Further, in the conventional heat conductive insulating resin molded body, the inorganic filler filled in the resin tends to aggregate, and it is difficult to form a continuous body formed by connecting the inorganic fillers, so that sufficient heat conductivity can be obtained. There was a problem that there was no.

INDUSTRIAL APPLICABILITY The present invention relates to a thermally conductive insulating elastomer molded body having excellent thermal conductivity and insulating properties even when the content of the inorganic filler is small, a method for producing the same, and thermal conductive insulation for obtaining the thermally conductive insulating elastomer molded body. It is an object of the present invention to provide an elastomer composition.

As a result of diligent studies to solve the above problems, the present inventors have found that the above object can be achieved by adding a triazinedithiol-based compound together with an inorganic filler to the thermally conductive insulating elastomer composition. The present invention has been completed.

（式中、Ｍ^１及びＭ^２はそれぞれ独立にＨ、Ｌｉ、Ｎａ、Ｋ、又はＣｓであり、Ｒ^１はＳ、Ｏ、又はＮＲ^３であり、Ｒ^３はＨ、又はアルキル基、ハロゲン化アルキル基、ヒドロキシアルキル基、アルコキシアルキル基、アルケニル基、ハロゲン化アルケニル基、ヒドロキシアルケニル基、アルコキシアルケニル基、フェニル基、ハロゲン化フェニル基、ヒドロキシフェニル基、アルコキシフェニル基、ビフェニル基、ハロゲン化ビフェニル基、ヒドロキシビフェニル基、アルコキシビフェニル基、ナフチル基、ハロゲン化ナフチル基、ヒドロキシナフチル基、アルコキシナフチル基、カルボキシル基、エステル基、ウレタン基、アゾ基、シアノ基、アミノ基、アミド基、及びアルコキシシリル基からなる群より選択される少なくとも１種の官能基を有する有機基であり、Ｒ^２は前記有機基と同じであり、あるいはＮＲ^３とＲ^２はヘテロ環を構成する。）
［２］
前記トリアジンジチオール系化合物は、下記一般式（２）～（４）で表されるトリアジンジチオール系化合物の少なくとも１種である［１］に記載の熱伝導性絶縁エラストマー組成物。

（式中、Ｍ^１、Ｍ^２、Ｒ^２、及びＲ^３は前記と同じである。）

（式中、Ｍ^１及びＭ^２は前記と同じであり、Ｒ^１はＳ、Ｏ、－ＮＨＣＨ_２ＣＨ_２Ｏ－、－Ｎ（ＣＨ_３）ＣＨ_２ＣＨ_２Ｏ－、－Ｎ（Ｃ_３Ｈ_７）ＣＨ_２ＣＨ_２Ｏ－、－ＮＨＣＨ_２ＣＨ_２ＣＨ_２ＣＨ_２Ｏ－、－Ｎ（Ｃ_２Ｈ_５）ＣＨ_２ＣＨ_２ＣＨ_２ＣＨ_２Ｏ－、－ＮＨＣＨ_２（ＣＨ_２）_８ＣＨ_２Ｏ－、－ＮＨＣＨ_２ＣＨ（ＣＨ_３）Ｏ－、－ＮＨＣ_６Ｈ_４Ｏ－、－Ｎ（Ｃ_２Ｈ_５）Ｃ_６Ｈ_４Ｏ－、－ＮＨＣ_１０Ｈ_６Ｏ－、－Ｎ（ＣＨ_２ＣＨ_２）_２ＣＨＯ－、－Ｎ（ＣＨ_２ＣＨ_２）_２ＮＣＨ_２ＣＨ_２Ｏ－、－Ｎ（ＣＨ_２ＣＨ_２ＯＨ）ＣＨ_２ＣＨ_２Ｏ－、－Ｎ（ＣＨ_２ＣＨ_２ＣＨ_２ＯＨ）ＣＨ_２ＣＨ_２ＣＨ_２Ｏ－、－Ｎ（ＣＨ_２ＣＨ（ＣＨ_３）ＯＨ）ＣＨ_２ＣＨ（ＣＨ_３）Ｏ－、－Ｎ（ＣＨ_２ＣＨ_２ＣＨ_２ＣＨ_２ＯＨ）ＣＨ_２ＣＨ_２ＣＨ_２ＣＨ_２Ｏ－、－ＮＨＣＨ_２Ｃ_６Ｈ_４Ｏ－、－ＮＨＣ_６Ｈ_１１Ｏ－、又は－Ｎ（Ｃ_３Ｈ_７）Ｃ_６Ｈ_４Ｏ－であり、Ｒ^４はアルキレン基であり、Ｒ^５はアルコキシ基であり、Ｒ^６及びＲ^７はそれぞれ独立にアルコキシ基又はアルキル基である。）

（式中、Ｍ^１、Ｍ^２、及びＲ^５～Ｒ^７は前記と同じであり、Ｒ^８は水素又はアルキル基であり、Ｒ^９はアルキレン基又はアルキレンオキシ基であり、Ｒ^８とＲ^９は互いに結合して環を形成してもよい。）
［３］
前記無機フィラーは、窒化アルミニウムフィラー及び窒化ホウ素フィラーからなる群より選択される少なくとも１種を含む［１］又は［２］に記載の熱伝導性絶縁エラストマー組成物。
［４］
前記無機フィラーの含有量は、前記エラストマー１００質量部に対して２０～４００質量部である［１］～［３］のいずれかに記載の熱伝導性絶縁エラストマー組成物。
［５］
前記トリアジンジチオール系化合物の含有量は、前記無機フィラー１００質量部に対して５×１０^－７～５質量部である［１］～［４］のいずれかに記載の熱伝導性絶縁エラストマー組成物。
［６］
［１］～［５］のいずれかに記載の熱伝導性絶縁エラストマー組成物から得られる熱伝導性絶縁エラストマー成形体。
［７］
前記熱伝導性絶縁エラストマー成形体は、熱伝導性絶縁エラストマーシートである［６］に記載の熱伝導性絶縁エラストマー成形体。
［８］
［６］又は［７］に記載の熱伝導性絶縁エラストマー成形体の製造方法であって、前記無機フィラーと前記トリアジンジチオール系化合物とを接触させて、前記無機フィラーの表面に前記トリアジンジチオール系化合物を付着させて表面修飾無機フィラーを得る工程Ａ、前記表面修飾無機フィラーを前記エラストマー中に分散させて前記熱伝導性絶縁エラストマー組成物を得る工程Ｂ、及び前記熱伝導性絶縁エラストマー組成物を成形する工程Ｃを含む熱伝導性絶縁エラストマー成形体の製造方法。
［９］
前記工程Ｃにおいて、前記熱伝導性絶縁エラストマー組成物を加圧及び／又は加熱して成形する［８］に記載の熱伝導性絶縁エラストマー成形体の製造方法。 That is, the present invention has the following configuration.
[1]
A thermally conductive insulating elastomer composition containing at least one elastomer selected from the group consisting of a silicone-based elastomer and a fluorine-based elastomer, an inorganic filler, and a triazinedithiol-based compound represented by the following general formula (1).

(In the formula, M ¹ and M ² are independently H, Li, Na, K, or Cs, R ¹ is S, O, or NR ³ , and R ³ is H, or an alkyl group, halogenated. Alkyl group, hydroxyalkyl group, alkoxyalkyl group, alkenyl group, halogenated alkenyl group, hydroxyalkenyl group, alkoxyalkenyl group, phenyl group, halogenated phenyl group, hydroxyphenyl group, alkoxyphenyl group, biphenyl group, halogenated biphenyl group , Hydroxybiphenyl group, alkoxybiphenyl group, naphthyl group, naphthyl halide group, hydroxynaphthyl group, alkoxynaphthyl group, carboxyl group, ester group, urethane group, azo group, cyano group, amino group, amide group, and alkoxysilyl group. It is an organic group having at least one functional group selected from the group consisting of, R ² is the same as the organic group, or NR ³ and R ² form a heterocycle).
[2]
The thermally conductive insulating elastomer composition according to [1], wherein the triazinedithiol-based compound is at least one of the triazinedithiol-based compounds represented by the following general formulas (2) to (4).

(In the formula, M ¹ , M ² , R ² and R ³ are the same as above.)

(In the formula, M ¹ and M ² are the same as described above, and R ¹ is S, O, -NHCH ₂ CH ₂ O-, -N (CH ₃ ) CH ₂ CH ₂ O-, -N (C ₃ H). ₇ ) CH ₂ CH ₂ O-, -NHCH ₂ CH ₂ CH ₂ CH ₂ O-, -N (C ₂ H ₅ ) CH ₂ CH ₂ CH ₂ CH ₂ O-, -NHCH ₂ (CH ₂ ) ₈ CH ₂ O-, -NHCH ₂ CH (CH ₃ ) O-, -NHC ₆ H ₄ O-, -N (C ₂ H ₅ ) C ₆ H ₄ O-, -NHC ₁₀ H ₆ O-, -N (CH ₂ ) CH ₂ ) ₂ CHO-, -N (CH ₂ CH ₂ ) ₂ NCH ₂ CH ₂ O-, -N (CH ₂ CH ₂ OH) CH ₂ CH ₂ O-, -N (CH ₂ CH ₂ CH ₂ OH) CH ₂ CH ₂ CH ₂ O-, -N (CH ₂ CH (CH ₃ ) OH) CH ₂ CH (CH ₃ ) O-, -N (CH ₂ CH ₂ CH ₂ CH ₂ OH) CH ₂ CH ₂ CH ₂ CH ₂ O-, -NHCH ₂ C ₆ H ₄ O-, -NHC ₆ H ₁₁ O-, or -N (C ₃ H ₇ ) C ₆ H ₄ O-, where R ⁴ is an alkylene group and R ⁵ is an alkoxy group, and R ⁶ and R ⁷ are independently alkoxy groups or alkyl groups, respectively.)

(In the formula, M ¹ , M ² and R ⁵ to R ⁷ are the same as above, R ⁸ is a hydrogen or alkyl group, R ⁹ is an alkylene or alkylene oxy group, R ⁸ and R ⁹ May combine with each other to form a ring.)
[3]
The thermally conductive insulating elastomer composition according to [1] or [2], wherein the inorganic filler contains at least one selected from the group consisting of an aluminum nitride filler and a boron nitride filler.
[4]
The thermally conductive insulating elastomer composition according to any one of [1] to [3], wherein the content of the inorganic filler is 20 to 400 parts by mass with respect to 100 parts by mass of the elastomer.
[5]
The thermally conductive insulating elastomer composition according to any one of [1] to [4], wherein the content of the triazinedithiol-based compound is 5 × 10 ^-7 to 5 parts by mass with respect to 100 parts by mass of the inorganic filler. ..
[6]
A thermally conductive insulating elastomer molded product obtained from the thermally conductive insulating elastomer composition according to any one of [1] to [5].
[7]
The thermally conductive insulating elastomer molded body according to [6], wherein the thermally conductive insulating elastomer molded body is a thermally conductive insulating elastomer sheet.
[8]
The method for producing a thermally conductive insulating elastomer molded product according to [6] or [7], wherein the inorganic filler is brought into contact with the triazinedithiol-based compound, and the triazinedithiol-based compound is brought onto the surface of the inorganic filler. Step A to obtain the surface-modified inorganic filler, step B to disperse the surface-modified inorganic filler in the elastomer to obtain the thermally conductive insulating elastomer composition, and molding the thermally conductive insulating elastomer composition. A method for producing a thermally conductive insulating elastomer molded product, which comprises the step C.
[9]
The method for producing a thermally conductive insulating elastomer molded product according to [8], wherein the thermally conductive insulating elastomer composition is formed by pressurizing and / or heating in the step C.

The thermally conductive insulating elastomer composition of the present invention contains a triazinedithiol-based compound together with an inorganic filler. By adhering the triazinedithiol-based compound to the surface of the inorganic filler, an inorganic filler surface-modified with the triazinedithiol-based compound (surface-modified inorganic filler) can be obtained. Since the surface-modified inorganic filler has higher dispersibility than the conventional inorganic filler, it is less likely to aggregate in the elastomer. Therefore, a continuum formed by connecting surface-modified inorganic fillers is likely to be formed in the elastomer. As a result, the thermally conductive insulating elastomer molded product obtained from the thermally conductive insulating elastomer composition of the present invention has excellent thermal conductivity even when the content of the inorganic filler is small.

Hereinafter, embodiments of the present invention will be described.

（式中、Ｍ^１及びＭ^２はそれぞれ独立にＨ、Ｌｉ、Ｎａ、Ｋ、又はＣｓであり、Ｒ^１はＳ、Ｏ、又はＮＲ^３であり、Ｒ^３はＨ、又はアルキル基、ハロゲン化アルキル基、ヒドロキシアルキル基、アルコキシアルキル基、アルケニル基、ハロゲン化アルケニル基、ヒドロキシアルケニル基、アルコキシアルケニル基、フェニル基、ハロゲン化フェニル基、ヒドロキシフェニル基、アルコキシフェニル基、ビフェニル基、ハロゲン化ビフェニル基、ヒドロキシビフェニル基、アルコキシビフェニル基、ナフチル基、ハロゲン化ナフチル基、ヒドロキシナフチル基、アルコキシナフチル基、カルボキシル基、エステル基、ウレタン基、アゾ基、シアノ基、アミノ基、アミド基、及びアルコキシシリル基からなる群より選択される少なくとも１種の官能基を有する有機基であり、Ｒ^２は前記有機基と同じであり、あるいはＮＲ^３とＲ^２はヘテロ環を構成する。） The thermally conductive insulating elastomer composition of the present invention comprises at least one elastomer selected from the group consisting of a silicone-based elastomer and a fluorine-based elastomer, an inorganic filler, and a triazinedithiol-based compound represented by the following general formula (1). Contains.

(In the formula, M ¹ and M ² are independently H, Li, Na, K, or Cs, R ¹ is S, O, or NR ³ , and R ³ is H, or an alkyl group, halogenated. Alkyl group, hydroxyalkyl group, alkoxyalkyl group, alkenyl group, halogenated alkenyl group, hydroxyalkenyl group, alkoxyalkenyl group, phenyl group, halogenated phenyl group, hydroxyphenyl group, alkoxyphenyl group, biphenyl group, halogenated biphenyl group , Hydroxybiphenyl group, alkoxybiphenyl group, naphthyl group, naphthyl halide group, hydroxynaphthyl group, alkoxynaphthyl group, carboxyl group, ester group, urethane group, azo group, cyano group, amino group, amide group, and alkoxysilyl group. It is an organic group having at least one functional group selected from the group consisting of, R ² is the same as the organic group, or NR ³ and R ² form a heterocycle).

<Elastomer>
Known silicone-based elastomers and fluorine-based elastomers can be used without particular limitation, and are appropriately selected depending on the intended use of the thermally conductive insulating elastomer molded product and the like. The elastomer may be used alone or in combination. Other elastomers such as polyester-based elastomers, polyamide-based elastomers, rubber-based elastomers, olefin-based elastomers, styrene-based elastomers, vinyl chloride-based elastomers, and polyurethane-based elastomers, and thermoplastic resins, as long as the effects of the present invention are not impaired. , The thermoplastic resin, and the rubber may be appropriately blended in the composition. These may be blended alone or in combination of two or more.

The silicone-based elastomer is not particularly limited, and examples thereof include those having a structural unit represented by the following general formula (5).

As the silicone-based elastomer, in the above general formula (5), polydimethylsiloxane in which all Rs are methyl groups, and some of the methyl groups are other alkyl groups, vinyl groups, phenyl groups, fluoroalkyl groups and the like. Examples thereof include various polyorganosiloxanes substituted with one or more substituents. These may be used alone or in combination of two or more.

In the general formula (5), n is not particularly limited, but is preferably an integer of 5 to 100,000.

From the viewpoint of heat resistance, the silicone-based elastomer is preferably a crosslinked type that is cured by an addition reaction or a peroxide. Examples of the crosslinked type silicone-based elastomer include those having two or more, preferably three or more alkenyl groups bonded to silicon atoms in one molecule. If the content of the alkenyl group bonded to the silicon atom is less than the above numerical range, the obtained composition will not be sufficiently cured when the curing is carried out by an addition reaction. A vinyl group is preferable as the alkenyl group. The alkenyl group may be bonded to either a silicon atom at the end of the molecular chain or a silicon atom other than the end of the molecular chain, but at least one alkenyl group is bonded to the silicon atom at the end of the molecular chain. Is preferable.

Examples of the silicone-based elastomer that is cured by the addition reaction include a dimethylsiloxane / methylvinylsiloxane copolymer having both ends of the molecular chain, a trimethylsiloxy group-blocking methylvinylpolysiloxane at both ends of the molecular chain, and a trimethylsiloxy having both ends of the molecular chain. Base-blocked dimethylsiloxane / methylvinylsiloxane / methylphenylsiloxane copolymer, molecular chain double-ended dimethylvinylsiloxy group-blocked dimethylpolysiloxane, molecular chain double-ended dimethylvinylsiloxy group-blocked methylvinylpolysiloxane, molecular chain double-ended dimethylvinylsiloxy Base-blocked dimethylsiloxane / methylvinylsiloxane copolymer, molecular chain double-ended dimethylvinylsiloxy group-blocked dimethylsiloxane / methylvinylsiloxane / methylphenylsiloxane copolymer, molecular chain double-ended trivinylsiloxy group-blocked dimethylpolysiloxane, etc. Can be mentioned. These may be used alone or in combination of two or more.

Examples of silicone-based elastomers that can be cured by peroxide include dimethylpolysiloxane with both ends of the molecular chain dimethylvinylsiloxy group sealed, dimethylpolysiloxane at both ends of the molecular chain, dimethylpolysiloxane, and dimethylvinylsiloxy group sealed at both ends of the molecular chain. Dimethylsiloxane / Methylphenylsiloxane copolymer, dimethylvinylsyloxy group-blocked dimethylsiloxane / methylvinylsiloxane copolymer at both ends of the molecular chain, trimethylsiloxy group-blocked dimethylsiloxane / methylvinylsiloxane copolymer at both ends of the molecular chain, both molecular chains Terminal dimethylvinyl siloxy group-blocked methyl (3,3,3-trifluoropropyl) polysiloxane, molecular chain double-ended silanol group-blocked dimethylsiloxane / methylvinylsiloxane copolymer, and molecular chain double-ended silanol group-blocked dimethylsiloxane / methyl Examples thereof include vinyl siloxane and methyl phenyl siloxane copolymers. These may be used alone or in combination of two or more.

When curing is performed by an addition reaction, for example, organohydrogenpolysiloxane is used as a curing agent, and the reaction is performed in the presence of a platinum-based catalyst. When curing is performed with a peroxide, for example, an organic peroxide is used as a curing agent. As the curing agent and the catalyst, those known in the art can be used.

The fluorine-based elastomer is not particularly limited, and is, for example, vinylidenefluorolide / hexafluoropropene-based copolymer, vinylidenefluorolide / hexafluoropropene / tetrafluoroethylene-based copolymer, tetrafluoroethylene / propylene-based copolymer, and the like. Can be mentioned. Further, these copolymers may be further copolymerized with ethylene or perfluoroalkyl vinyl ether. In addition, it is a block copolymer of fluororubber (vinylidenefluorolide / hexafluoropropene / tetrafluoroethylene-based copolymer) and fluororesin (tetrafluoroethylene / ethylene alternating copolymer and polyvinylidenefluorolide). Thermoplastic elastomers can also be used. These may be used alone or in combination of two or more.

Further, as the fluoroelastomer, a perfluoroelastomer can also be used. Examples of the perfluoroelastomer include a perfluoroolefin, a perfluorovinyl ether selected from the group consisting of a perfluoro (alkyl vinyl) ether, a perfluoro (alkoxyvinyl) ether, and a mixture thereof, and a copolymer of a cured site monomer. Examples thereof include perfluoroelastomers containing a polymerization unit.

Examples of the cured site monomer include a cured site monomer containing iodine and bromine, and a cured site monomer containing a cyano group. Examples of the cured site monomer containing iodine and bromine include CF ₂ = CF (CF ₂ ) _n I, CF ₂ = CF (CF ₂ ) _n Br, and I (CF ₂ ) _n I. Examples of the cured site monomer containing a cyano group include cyano group-containing perfluorovinyl ether, and specifically, CF ₂ = CFO (CF ₂ ) _n OCF (CF ₃ ) CN (n: 2 to 4). ), CF ₂ = CFO (CF ₂ ) _n CN (n: 2-12), CF ₂ = CFO [CF ₂ CF (CF ₃ ) O] _m (CF ₂ ) _n CN (n: 2, m: 1 ～ 5), CF ₂ = CFO [CF ₂ CF (CF ₃ ) O] _m (CF ₂ ) _n CN (n: 1 to 4, m: 1 to 2), and CF ₂ = CFO [CF ₂ CF (CF ₃ ) ) O] _n CF ₂ CF (CF ₃ ) CN (n: 0 to 4) and the like. The perfluoroelastomer may be synthesized by a known method, or a commercially available one may be used.

<Inorganic filler>
As the inorganic filler, known ones can be used without particular limitation. Examples of the inorganic filler include aluminum, copper, nickel; alumina, magnesium oxide, beryllium oxide, chromium oxide, titanium oxide; boron nitride, aluminum nitride, silicon nitride, titanium nitride, tantalum nitride, chromium nitride; titanium boride, hoof. Zirconium boro, hafnium borohydride, ittrium borohydride, vanadium borohydride, magnesium boroborohydride, niobium borohydride, tantalum borohydride, talium borohydride; boron carbide, titanium carbide, zirconium carbide, vanadium carbide, niobium carbide, tantalum carbide, Chromium carbide, molybdenum carbide, tungsten carbide, tungsten carbide II tungsten carbide; Fe-Si alloy, Fe-Al alloy, Fe-Si-Al alloy, Fe-Si-Cr alloy, Fe-Ni alloy, Fe-Ni-Co alloy , Fe-Ni-Mo alloy, Fe-Co alloy, Fe-Si-Al-Cr alloy, Fe-Si-B alloy, Fe-Si-Co-B alloy; Mn-Zn ferrite, Mn-Mg-Zn ferrite, Examples thereof include Mg-Cu-Zn ferrite, Ni-Zn ferrite, Ni-Cu-Zn ferrite, Cu-Zn ferrite and the like. These may be used alone or in combination of two or more.

Of these, from the viewpoint of thermal conductivity and electrical insulation, alumina, magnesium oxide, magnesium oxide, beryllium oxide, chromium oxide, titanium oxide, boron nitride, aluminum nitride, silicon nitride, titanium nitride, chromium nitride, etc. are preferable. Selected from the group consisting of tantalum nitride, titanium borate, zirconium borate, hafnium borate, ittrium borate, vanadium borate, magnesium diboride, niobium borate, tantalum borate, tallium borate, and molybdenum borate. Alumina, magnesium oxide, magnesium oxide, beryllium oxide, chromium oxide, titanium oxide, boron nitride, aluminum nitride, silicon nitride, titanium nitride, chromium nitride, titanium boride, zirconium borate. , Hafnium boride, ittrium borate, vanadium borate, magnesium boride, niobium borate, tantalum borate, tallium borate, and molybdenum borate, more preferably at least one selected from the group. , At least one selected from the group consisting of aluminum nitride and boron nitride.

The inorganic filler is preferably particles having no extreme difference in length, width, and thickness, and the aspect ratio is preferably 0.8 to 1.0. The shape of the inorganic filler may be not only spherical but also a polyhedron such as a needle, a lump, a cube or an icosidodecahedron.

The particle size of the inorganic filler is not particularly limited, but is preferably 0.1 to 500 μm, more preferably 0.5 to 300 μm, still more preferably 1 to 200 μm or more, and when the particle size exceeds 500 μm, the thermal conductivity is increased. It is not preferable from the viewpoint of surface appearance, and if the particle size is less than 0.1 μm, the dispersibility is lowered and the cost is increased, which tends to be unfavorable.

The content of the inorganic filler in the heat conductive insulating elastomer composition is not particularly limited, but is preferably 20 to 400 parts by mass with respect to 100 parts by mass of the elastomer from the viewpoint of obtaining excellent heat conductivity. It is preferably 25 to 350 parts by mass, more preferably 30 to 300 parts by mass, and if it is less than 20 parts by mass, the thermal conductivity tends to decrease, and if it exceeds 400 parts by mass, the flexibility tends to decrease. It is in.

（式中、Ｍ^１及びＭ^２はそれぞれ独立にＨ、Ｌｉ、Ｎａ、Ｋ、又はＣｓであり、Ｒ^１はＳ、Ｏ、又はＮＲ^３であり、Ｒ^３はＨ、又はアルキル基、ハロゲン化アルキル基、ヒドロキシアルキル基、アルコキシアルキル基、アルケニル基、ハロゲン化アルケニル基、ヒドロキシアルケニル基、アルコキシアルケニル基、フェニル基、ハロゲン化フェニル基、ヒドロキシフェニル基、アルコキシフェニル基、ビフェニル基、ハロゲン化ビフェニル基、ヒドロキシビフェニル基、アルコキシビフェニル基、ナフチル基、ハロゲン化ナフチル基、ヒドロキシナフチル基、アルコキシナフチル基、カルボキシル基、エステル基、ウレタン基、アゾ基、シアノ基、アミノ基、アミド基、及びアルコキシシリル基からなる群より選択される少なくとも１種の官能基を有する有機基であり、Ｒ^２は前記有機基と同じであり、あるいはＮＲ^３とＲ^２はヘテロ環を構成する。） <Triazinedithiol compound>
The triazinedithiol-based compound used in the present invention is represented by the following general formula (1). The triazinedithiol-based compound may be used alone or in combination of two or more.

(In the formula, M ¹ and M ² are independently H, Li, Na, K, or Cs, R ¹ is S, O, or NR ³ , and R ³ is H, or an alkyl group, halogenated. Alkyl group, hydroxyalkyl group, alkoxyalkyl group, alkenyl group, halogenated alkenyl group, hydroxyalkenyl group, alkoxyalkenyl group, phenyl group, halogenated phenyl group, hydroxyphenyl group, alkoxyphenyl group, biphenyl group, halogenated biphenyl group , Hydroxybiphenyl group, alkoxybiphenyl group, naphthyl group, naphthyl halide group, hydroxynaphthyl group, alkoxynaphthyl group, carboxyl group, ester group, urethane group, azo group, cyano group, amino group, amide group, and alkoxysilyl group. It is an organic group having at least one functional group selected from the group consisting of, R ² is the same as the organic group, or NR ³ and R ² form a heterocycle).

The alkyl group may be linear, branched, or cyclic. The number of carbon atoms of the alkyl group is not particularly limited, but is preferably 1 to 40, more preferably 1 to 30.

The alkenyl group may be linear, branched or cyclic. The number of carbon atoms of the alkenyl group is not particularly limited, but is preferably 1 to 40, more preferably 1 to 30.

The halogen is not particularly limited, and examples thereof include fluorine, chlorine, bromine, and iodine.

The number of carbon atoms of the alkoxy group is not particularly limited, but is preferably 1 to 40, more preferably 1 to 30.

（式中、Ｍ^１、Ｍ^２、Ｒ^２、及びＲ^３は前記と同じである。） The triazinedithiol-based compound is preferably at least one of the triazinedithiol-based compounds represented by the following general formulas (2) to (4).

(In the formula, M ¹ , M ² , R ² and R ³ are the same as above.)

In the general formula (2), R ³ is preferably -H, -CH ₃ , -C ₂ H ₅ , -C ₃ H ₇ , -CH ₂ CH ₂ CN, or -CH ₂ CH = CH ₂ . Yes, R ² is preferably -C ₈ H ₁₆ CH = CHC ₈ H ₁₇ , -C ₈ H ₁₆ CH = CH ₂ , -C ₆ H ₄ CH = CHC ₆ H ₅ , -C ₆ H ₄ CH = CHC ₆ H ₄ OCH ₃ , -C ₆ H ₄ CH = CH ₂ , -CH ₂ C ₆ H ₄ CH = CH ₂ , -CH ₂ CH = CH ₂ , -CH ₂ NHCOC (CH ₃ ) = CH ₂ ,- C ₆ H ₄ NHC ₆ H ₅ , -C ₆ H ₄ N = NC ₆ H ₅ , -C ₆ H ₂ [C (CH ₃ ) ₃ ] ₂ OH, -C ₆ H ₄ C ₆ H ₅ , -C ₆ H ₄ C ₆ H ₄ C ₆ H ₅ , -CH ₂ COOH, -CH ₂ COOC ₂ H ₅ , -CH ₂ COOC ₈ H ₁₇ , -CH ₂ CH (C ₆ H ₅ ) ₂ , -CH ₂ CH ₂ OH , -CH ₂ CH ₂ CH ₂ CH ₂ OH, -CH ₂ (CH ₂ ) ₈ CH ₂ OH, -CH ₂ CH (CH ₃ ) OH, -C ₆ H ₄ OH, -C ₁₀ H ₆ OH, -CH ₂ C ₄ F ₉ , -CH ₂ C ₆ F ₁₃ , -CH ₂ C ₇ F ₁₅ , -CH ₂ C ₈ F ₁₇ , -CH ₂ CH ₂ C ₄ F ₉ , -CH ₂ CH ₂ C ₆ F ₁₃ , -CH ₂ CH ₂ C ₈ F ₁₇ , -CH ₂ CH ₂ C ₁₀ F ₂₁ , -CH ₂ CH ₂ CH ₂ C ₈ F ₁₇ , -C ₆ H ₄ C ₈ F ₁₇ , -C ₆ H ₄ C ₄ F ₉ , -C ₆ F ₅ , -C ₃ H ₆ Si (OCH ₃ ) ₃ , -C ₄ H ₈ Si (OCH ₃ ) ₃ , -C ₆ H ₁₂ Si (OCH ₃ ) ₃ , -C ₁₀ H ₂₀ Si (OCH ₃ ) ₃ , -CH ₂ CH ₂ NHC ₃ H ₆ Si (OCH ₃ ) ₃ , -C ₃ H ₆ Si (OC ₂ H ₅ ) ₃ , -C ₃ H ₆ Si (OCH ₃ ) ₂ CH ₃ , -C ₃ H ₆ Si (CH ₃ ) ₂ OCH ₃ or -C ₃ H ₆ Si (CH ₃ ) ₂ OSI (CH ₃ ) ₃ .

Alternatively, in the general formula (2), R ³ and R ² are the same, preferably -CH ₂ CH = CH ₂ , -C ₈ H ₁₆ CH = CH C ₈ H ₁₇ , -C ₈ H ₁₆ CH. = CH ₂ , -C ₆ H ₄ CH = CHC ₆ H ₅ , -C ₆ H ₄ CH = CHC ₆ H ₄ OCH ₃ , -C ₆ H ₄ CH = CH ₂ , -CH ₂ C ₆ H ₄ CH = CH ₂ , -CH ₂ CH = CH ₂ , -CH ₂ NHCOC (CH ₃ ) = CH ₂ , -C ₆ H ₄ NHC ₆ H ₅ , -C ₆ H ₄ N = NC ₆ H ₅ , -C ₆ H ₂ [ C (CH ₃ ) ₃ ] ₂ OH, -C ₆ H ₄ C ₆ H ₅ , -C ₆ H ₄ C ₆ H ₄ C ₆ H ₅ , -CH ₂ COOH, -CH ₂ COOC ₂ H ₅ , -CH ₂ COOC ₈ H ₁₇ , -CH ₂ CH (C ₆ H ₅ ) ₂ , -CH ₂ CH ₂ OH, -CH ₂ CH ₂ CH ₂ CH ₂ OH, -CH ₂ (CH ₂ ) ₈ CH ₂ OH, -CH ₂ CH (CH ₃ ) OH, -C ₆ H ₄ OH, -C ₁₀ H ₆ OH, -CH ₂ C ₄ F ₉ , -CH ₂ C ₆ F ₁₃ , -CH ₂ C ₈ F ₁₇ , -CH ₂ CH ₂ C ₄ F ₉ , -CH ₂ CH ₂ C ₆ F ₁₃ , -CH ₂ CH ₂ C ₈ F ₁₇ , -CH ₂ CH ₂ C ₁₀ F ₂₁ , -CH ₂ CH ₂ CH ₂ C ₈ F ₁₇ , -C ₆ H ₄ C ₈ F ₁₇ , -C ₆ H ₄ C ₄ F ₉ , -C ₆ F ₅ , -C ₃ H ₆ Si (OCH ₃ ) ₃ , -C ₄ H ₈ Si (OCH ₃ ) ₃ , -C ₆ H ₁₂ Si (OCH ₃ ) ₃ , -C ₁₀ H ₂₀ Si (OCH ₃ ) ₃ , -CH ₂ CH ₂ NHC ₃ H ₆ Si (OCH ₃ ) ₃ , -C ₃ H ₆ Si (OC ₂ H ₅ ) ₃ , -C ₃ H ₆ Si (OCH ₃ ) ₂ CH ₃ , -C ₃ H ₆ Si (CH ₃ ) ₂ OCH ₃ , or -C ₃ H ₆ Si (CH ₃ ) ₂ OSi (CH ₃ ) ₃ .

Alternatively, in the general formula (2), N, R ³ and R ² form a heterocycle, and R ³ and R ² are preferably − (CH ₂ CH ₂ ) ₂ CHOH, − (CH ₂ CH ₂ ). ) ₂ CHOCOC ₈ H ₁₇ CH = CH ₂ ,-(CH ₂ CH ₂ ) ₂ CHOCH ₃ or-(CH ₂ CH ₂ ) ₂ CHOCOC (CH ₃ ) = CH ₂ .

（式中、Ｍ^１及びＭ^２は前記と同じであり、Ｒ^１はＳ、Ｏ、－ＮＨＣＨ_２ＣＨ_２Ｏ－、－Ｎ（ＣＨ_３）ＣＨ_２ＣＨ_２Ｏ－、－Ｎ（Ｃ_３Ｈ_７）ＣＨ_２ＣＨ_２Ｏ－、－ＮＨＣＨ_２ＣＨ_２ＣＨ_２ＣＨ_２Ｏ－、－Ｎ（Ｃ_２Ｈ_５）ＣＨ_２ＣＨ_２ＣＨ_２ＣＨ_２Ｏ－、－ＮＨＣＨ_２（ＣＨ_２）_８ＣＨ_２Ｏ－、－ＮＨＣＨ_２ＣＨ（ＣＨ_３）Ｏ－、－ＮＨＣ_６Ｈ_４Ｏ－、－Ｎ（Ｃ_２Ｈ_５）Ｃ_６Ｈ_４Ｏ－、－ＮＨＣ_１０Ｈ_６Ｏ－、－Ｎ（ＣＨ_２ＣＨ_２）_２ＣＨＯ－、－Ｎ（ＣＨ_２ＣＨ_２）_２ＮＣＨ_２ＣＨ_２Ｏ－、－Ｎ（ＣＨ_２ＣＨ_２ＯＨ）ＣＨ_２ＣＨ_２Ｏ－、－Ｎ（ＣＨ_２ＣＨ_２ＣＨ_２ＯＨ）ＣＨ_２ＣＨ_２ＣＨ_２Ｏ－、－Ｎ（ＣＨ_２ＣＨ（ＣＨ_３）ＯＨ）ＣＨ_２ＣＨ（ＣＨ_３）Ｏ－、－Ｎ（ＣＨ_２ＣＨ_２ＣＨ_２ＣＨ_２ＯＨ）ＣＨ_２ＣＨ_２ＣＨ_２ＣＨ_２Ｏ－、－ＮＨＣＨ_２Ｃ_６Ｈ_４Ｏ－、－ＮＨＣ_６Ｈ_１１Ｏ－、又は－Ｎ（Ｃ_３Ｈ_７）Ｃ_６Ｈ_４Ｏ－であり、Ｒ^４はアルキレン基であり、Ｒ^５はアルコキシ基であり、Ｒ^６及びＲ^７はそれぞれ独立にアルコキシ基又はアルキル基である。）

(In the formula, M ¹ and M ² are the same as described above, and R ¹ is S, O, -NHCH ₂ CH ₂ O-, -N (CH ₃ ) CH ₂ CH ₂ O-, -N (C ₃ H). ₇ ) CH ₂ CH ₂ O-, -NHCH ₂ CH ₂ CH ₂ CH ₂ O-, -N (C ₂ H ₅ ) CH ₂ CH ₂ CH ₂ CH ₂ O-, -NHCH ₂ (CH ₂ ) ₈ CH ₂ O-, -NHCH ₂ CH (CH ₃ ) O-, -NHC ₆ H ₄ O-, -N (C ₂ H ₅ ) C ₆ H ₄ O-, -NHC ₁₀ H ₆ O-, -N (CH ₂ ) CH ₂ ) ₂ CHO-, -N (CH ₂ CH ₂ ) ₂ NCH ₂ CH ₂ O-, -N (CH ₂ CH ₂ OH) CH ₂ CH ₂ O-, -N (CH ₂ CH ₂ CH ₂ OH) CH ₂ CH ₂ CH ₂ O-, -N (CH ₂ CH (CH ₃ ) OH) CH ₂ CH (CH ₃ ) O-, -N (CH ₂ CH ₂ CH ₂ CH ₂ OH) CH ₂ CH ₂ CH ₂ CH ₂ O-, -NHCH ₂ C ₆ H ₄ O-, -NHC ₆ H ₁₁ O-, or -N (C ₃ H ₇ ) C ₆ H ₄ O-, where R ⁴ is an alkylene group and R ⁵ is an alkoxy group, and R ⁶ and R ⁷ are independently alkoxy groups or alkyl groups, respectively.)

In the general formula (3), the carbon number of the alkylene group of ^R4 is not particularly limited, but is preferably 1 to 40, more preferably 1 to 30. The number of carbon atoms of the alkoxy groups of R ⁵ to R ⁷ is not particularly limited, but is preferably 1 to 30, and more preferably 1 to 20. The number of carbon atoms of the alkyl groups of R ⁶ and R ⁷ is not particularly limited, but is preferably 1 to 30, and more preferably 1 to 20.

（式中、Ｍ^１、Ｍ^２、及びＲ^５～Ｒ^７は前記と同じであり、Ｒ^８は水素又はアルキル基であり、Ｒ^９はアルキレン基又はアルキレンオキシ基であり、Ｒ^８とＲ^９は互いに結合して環を形成してもよい。）

(In the formula, M ¹ , M ² and R ⁵ to R ⁷ are the same as above, R ⁸ is a hydrogen or alkyl group, R ⁹ is an alkylene or alkylene oxy group, R ⁸ and R ⁹ May combine with each other to form a ring.)

In the general formula (4), the number of carbon atoms of the alkoxy groups of R5 to ^R7 is not particularly limited, but is preferably ¹ to 30, and more preferably 1 to 20. The number of carbon atoms of the alkyl groups of R ⁶ and R ⁷ is not particularly limited, but is preferably 1 to 30, and more preferably 1 to 20. The number of carbon atoms of the alkyl group of R8 is not particularly limited, but is preferably ¹ to 30, and more preferably 1 to 20. The carbon number of the alkylene group or the alkyleneoxy group of R ⁹ is not particularly limited, but is preferably 1 to 20, and more preferably 1 to 15. Examples of the ring formed by bonding R ⁸ and R ⁹ include a 5-membered ring and a 6-membered ring, and the rings R ⁸ and R ⁹ are bonded to form a propantriyl group (5-membered ring). Case), butantryyl group (when forming a 6-membered ring), etc. are formed.

The triazinedithiol-based compound represented by the general formula (1) can be produced by a known method.

For example, the triazinedithiol-based compound represented by the general formula (2) can be synthesized by mixing triazinetrithiol or a derivative thereof with amines represented by NHR ² R ³ and reacting them. .. In this reaction, hydrogen sulfide is produced as a by-product.

The triazinedithiol-based compound represented by the general formula (3) is obtained by mixing triazinetrithiol or a derivative thereof with an alkoxysilylalkyl isocyanate represented by NCO-R ⁴ -SiR ⁵ R ⁶ R ⁷ . It can be synthesized by reacting. Examples of the alkoxysilylalkyl isocyanate include 3-trimethoxysilylpropyl isocyanate and 3-triethoxysilylpropyl isocyanate.

（式中、Ｒ^５～Ｒ^９は前記と同じである。） The triazinedithiol-based compound represented by the general formula (4) is prepared by mixing triazinetrithiol or a derivative thereof with an epoxy group-containing alkoxysilane represented by the following general formula (6) and reacting them. Can be synthesized.

( ^In the formula, R5 to ^R9 are the same as above.)

Examples of the epoxy group-containing alkoxysilane include diethoxy (3-glycidyl) methylsilane, 2- (3,4-epoxycyclohexyl) ethyltrimethoxysilane, 3-glycidylpropyl (dimethoxy) methylsilane, and 3-glycidylpropyltrimethoxysilane. , Diethoxy (3-glycidyloxy) methylsilane, 3-glycidyloxypropyl (dimethoxy) methylsilane, 3-glycidyloxypropyltrimethoxysilane and the like.

The reaction is preferably carried out by mixing the raw materials by dispersing or dissolving them in a solvent and further heating and reacting them. Thereby, the target product can be easily synthesized in a short time.

Solvents include, for example, water; alcohols such as methanol, ethanol, ethylene glycol, isopropanol, propylene glycol, carbitol, and cellsolve; ketones such as acetone, methyl ethyl ketone, and cyclohexanone; ethyl acetate, methyl benzoate, phthalic acid. Ethers such as diethyl, diethyl adipate, dibutyl ether, and anisole; aromatic hydrocarbons such as benzene, toluene, xylene, and decalin; polar solvents such as dimethylformamide, dimethylsulfoxide, hexamethylphosphoamide, and methylpyrrolidone. , Or a mixed solvent thereof and the like.

The concentration of triazine trithiol or a derivative thereof in the solvent is not particularly limited, but is usually 0.1 to 500 g / L, preferably 1 to 100 g / L. When the concentration of triazine trithiol or its derivative is less than 1 g / L, the reaction efficiency tends to be poor, while when the concentration exceeds 100 g / L, the viscosity of the solution or dispersion medium becomes too high and stirring is performed. Becomes difficult and a uniform reaction is less likely to occur.

The reaction temperature cannot be uniquely set because it is related to the boiling point of the solvent used, but is usually 0 to 200 ° C, preferably 30 to 160 ° C. Below 30 ° C., the reaction time becomes long and the productivity tends to decrease. Further, when the temperature exceeds 160 ° C., the reaction rate is increased and the productivity is improved, but by-products such as dimers are produced, and a special operation may be required for separation from the target product.

After completion of the reaction, the triazinedithiol compound can be obtained as white crystals or liquid by distilling off the solvent, which can be purified by solvent extraction or washing, or by distillation or crystallization. Is. In addition, when a by-product is produced, a step of converting the target product into a sodium salt in water, removing the insoluble material, neutralizing the solubilized product with a 1% -HCl solution, and purifying the product should be added. Is preferable.

The content of the triazinedithiol-based compound in the heat conductive insulating elastomer composition is not particularly limited, but from the viewpoint of obtaining excellent heat conductivity, it is preferably 5 × 10 ^-7 to 100 parts by mass of the inorganic filler. 5 parts by mass, more preferably 1 × 10 ^-6 to 4 parts by mass, further preferably 1.5 × 10 ^-6 to 3 parts by mass, and less than 5 × 10 ^-7 parts by mass, thermal conductivity and dispersibility. Tends to decrease, and if it exceeds 5 parts by mass, the cost tends to increase.

<Other ingredients>
It is preferable to add an antioxidant such as an aromatic amine-based, a hindered phenol-based, a phosphorus-based, and a sulfur-based antioxidant to the thermally conductive insulating elastomer composition. These may be used alone or in combination of two or more.

Examples of the aromatic amine-based antioxidant include phenylnaphthylamine, 4,4'-dimethoxydiphenylamine, 4,4'-bis (α, α-dimethylbenzyl) diphenylamine, and 4-isopropoxydiphenylamine. These may be used alone or in combination of two or more.

Examples of the hindered phenolic antioxidant include 3,5-di-t-butyl-4-hydroxy-toluene and n-octadecyl-β- (4'-hydroxy-3', 5'-di-t-. Butylphenyl) propionate, tetrakis [methylene-3- (3', 5'-di-t-butyl-4'-hydroxyphenyl) propionate] methane, 1,3,5-trimethyl-2,4,6'-tris (3,5-di-t-butyl-4-hydroxybenzyl) benzene, calcium (3,5-di-t-butyl-4-hydroxy-benzyl-monoethyl-phosphate), triethylene glycol-bis [3 -(3-t-Butyl-5-methyl-4-hydroxyphenyl) propionate], penterislityl-tetrakis [3- (3,5-di-t-butylanilino) -1,3,5-triazine, 3,9- Bis [1,1-dimethyl-2- {β- (3-t-butyl-4-hydroxy-5-methylphenyl) propionyloxy} ethyl] 2,4,8,10-tetraoxaspiro [5,5] Undecane, bis [3,3-bis (4'-hydroxy-3'-t-butylphenyl) butyl acid] glycol ester, triphenol, 2,2'-ethylidenebis (4,6-di-t-butylphenol), N, N'-bis [3- (3,5-di-t-butyl-4-hydroxyphenyl) propionyl] hydrazine, 2,2'-oxamidbis [ethyl-3- (3,5-di-t-butyl) -4-Hydroxyphenyl) propionate], 1,1,3-tris (3', 5'-di-t-butyl-4'-hydroxybenzyl) -S-triazine-2,4,6 (1H, 3H, 5H) -Trione, 1,3,5-Tris (4-t-butyl-3-hydroxy-2,6-dimethylbenzyl) isocyanurate, 3,5-di-t-butyl-4-hydroxyhydrocinnamic acid Hydrotriester with-1,3,5-tris (2-hydroxyethyl) -S-triazine-2,4,6 (1H, 3H, 5H), and N, N-hexamethylenebis (3,5-di) -T-Butyl-4-hydroxy-hydrocinnaamide) and the like. These may be used alone or in combination of two or more.

Examples of the phosphorus-based antioxidant include compounds containing phosphorus such as phosphoric acid, phosphite, hypophosphite derivative, phenylphosphonic acid, polyphosphonate, and diphosphite-based compound. Specific examples include triphenylphosphine, diphenyldecylphosphite, phenyldiisodecylphosphite, tri (nonylphenyl) phosphite, bis (2,4-di-t-butylphenyl) pentaerythritol diphosphite, and bis ( 2,6-di-t-butyl-4-methylphenyl) pentaerythritol diphosphite and the like can be mentioned. These may be used alone or in combination of two or more.

Examples of the sulfur-based antioxidant include sulfur-containing compounds such as thioether-based, dithioate-based, mercaptobenzimidazole-based, thiocarbanilide-based, and thiodipropion ester-based compounds. Specific examples include dilaurylthiodipropionate, distearylthiodipropionate, didodecylthiodipropionate, ditetradecylthiodipropionate, dioctadecylthiodipropionate, and pentaerythritol tetrakis (3-dodecylthiopro). Pionate), thiobis (N-phenyl-β-naphthylamine), 2-mercaptobenzothiazole, 2-mercaptobenzimidazole, tetramethylthiuram monosulfide, tetramethylthiuram disulfide, nickeldibutyldithiocarbamate, nickelisopropylxanthate, and Examples thereof include trilauryl trithiophosphite. These may be used alone or in combination of two or more.

The blending (content) amount of the antioxidant is preferably 0.01 to 3 parts by mass, more preferably 0.05 to 2 parts by mass, and further preferably 0.1 to 1 part by mass with respect to 100 parts by mass of the elastomer. be. When two or more kinds of antioxidants are blended, the total amount of the antioxidants blended is preferably 5 parts by mass or less.

A cross-linking agent may be added to the thermally conductive insulating elastomer composition, if necessary, as long as the effect of the present invention is not impaired. The cross-linking agent is not particularly limited as long as it is a cross-linking agent that reacts with the functional group of the elastomer. Examples thereof include agents, melamine resin-based cross-linking agents, metal salt-based cross-linking agents, metal chelate-based cross-linking agents, and amino resin-based cross-linking agents. These may be used alone or in combination of two or more.

The epoxy-based cross-linking agent is not particularly limited as long as it is a polyfunctional epoxy compound having two or more epoxy groups (glycidyl groups) in the molecule, and specifically, 1,6-dihydroxyx having two epoxy groups. Naphthalenediglycidyl ether, 1,3-bis (oxylanylmethoxy) benzene, 1,3,5-tris (2,3-epoxypropyl) -1,3,5-triazine-2, with three epoxy groups, 4,6 (1H, 3H, 5H) -trione and diglycerol triglycidyl ether, 1-chloro-2,3-epoxypropane, formaldehyde, 2,7-naphthalenediol polycondensate and pentaerythritol with four epoxy groups Examples include polyglycidyl ether. Of these, a polyfunctional epoxy compound having heat resistance in the skeleton is preferable. In particular, a bifunctional or tetrafunctional epoxy compound having a naphthalene structure as a skeleton, or a trifunctional epoxy compound having a triazine structure as a skeleton is preferable.

In addition, a vinyl aromatic monomer containing two or more glycidyl groups per molecule and having a weight average molecular weight of 4000 to 25000, (X) 20 to 99% by mass, and (Y) 1 to 80% by mass glycidyl. Examples thereof include a styrene-based polymer composed of (meth) acrylate and (Z) a vinyl group-containing monomer other than (X) which does not contain 0 to 79% by mass of an epoxy group. A copolymer composed of 20 to 99% by mass of (X), 1 to 80% by mass of (Y), and 0 to 40% by mass of (Z) is more preferable, and 25 to 90% of (X) is more preferable. It is a copolymer consisting of mass%, (Y) 10 to 75% by mass, and (Z) 0 to 35% by mass. Examples of the (X) vinyl aromatic monomer include styrene and α-methylstyrene. Examples of the (Y) glycidyl (meth) acrylate include glycidyl (meth) acrylic acid, (meth) acrylic acid ester having a cyclohexene oxide structure, (meth) acrylic glycidyl ether, and the like, and among these, reactive. Glysidyl (meth) acrylate is preferred because of its high value. Examples of the (Z) other vinyl group-containing monomer include methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, butyl (meth) acrylate, and 2-ethylhexyl (meth) acrylate. It has an alkyl group having 1 to 22 carbon atoms (the alkyl group may be a straight chain or a branched chain) such as cyclohexyl (meth) acrylate, stearyl (meth) acrylate, and methoxyethyl (meth) acrylate (meth). Acrylic acid alkyl ester, (meth) acrylic acid polyalkylene glycol ester, (meth) acrylic acid alkoxyalkyl ester, (meth) acrylic acid hydroxyalkyl ester, (meth) acrylic acid dialkylaminoalkyl ester, (meth) acrylic acid benzyl ester , (Meta) acrylic acid phenoxyalkyl ester, (meth) acrylic acid isobornyl ester, (meth) acrylic acid alkoxysilylalkyl ester and the like. Further, vinyl esters such as (meth) acrylamide, (meth) acrylic dialkylamide, and vinyl acetate, vinyl ethers, aromatic vinyl monomers such as (meth) allyl ethers, and α-olefins such as ethylene and propylene. Monomers and the like can also be used as the above-mentioned (Z) and other vinyl group-containing monomers.

The weight average molecular weight of the styrene-based copolymer is preferably 4000 to 25000, and more preferably 5000 to 15000. The epoxy value of the styrene-based copolymer is preferably 400 to 2500 equivalents / 1 × 10 ⁶ g, more preferably 500 to 1500 equivalents / 1 × 10 ⁶ g, still more preferably 600 to 1000 equivalents / 1. × 10 ⁶ g.

The carbodiimide-based cross-linking agent is not particularly limited as long as it is a polycarbodiimide having two or more carbodiimide groups (-N = C = N- structure) in one molecule, and is, for example, an aliphatic polycarbodiimide or an alicyclic poly. Examples include carbodiimides, aromatic polycarbodiimides, and copolymers thereof. It is preferably an aliphatic polycarbodiimide or an alicyclic polycarbodiimide.

Polycarbodiimide can be obtained, for example, by a decarbonization reaction of a diisocyanate compound. Examples of the diisocyanate compound include 4,4'-diphenylmethane diisocyanate, 4,4'-diphenyldimethylmethane diisocyanate, 1,3-phenylenediocyanate, 1,4-phenylenediocyanate, 2,4-tolylene diisocyanate, and 2,6. -Toluene diisocyanate, 1,5-naphthylene diisocyanate, hexamethylene diisocyanate, dicyclohexylmethane diisocyanate, cyclohexane-1,4-diisocyanate, xylylene diisocyanate, isophorone diisocyanate, methylcyclohexane diisocyanate, tetramethylxylylene diisocyanate, 1,3 Examples thereof include 5-triisopropylphenylene-2,4-diisocyanate. Only one of these may be used, or two or more thereof may be copolymerized and used. Further, a branched structure may be introduced, or a functional group other than a carbodiimide group or an isocyanate group may be introduced by copolymerization. Further, although the terminal isocyanate can be used as it is, the degree of polymerization may be controlled by reacting the terminal isocyanate, or a part of the terminal isocyanate may be blocked.

As the polycarbodiimide, alicyclic polycarbodiimide derived from dicyclohexylmethane diisocyanate, cyclohexane-1,4-diisocyanate, isophorone diisocyanate and the like is preferable, and more preferably dicyclohexylmethane diisocyanate and alicyclic polycarbodiimide derived from isophorone diisocyanate. Is.

From the viewpoint of stability and handleability, the polycarbodiimide preferably contains 2 to 50 carbodiimide groups per molecule, more preferably 5 to 30 groups. The number of carbodiimides in the polycarbodiimide molecule (that is, the number of carbodiimide groups) corresponds to the degree of polymerization if the polycarbodiimide is obtained from a diisocyanate compound. For example, the degree of polymerization of polycarbodiimide obtained by connecting 21 diisocyanate compounds in a chain is 20 and the number of carbodiimide groups in the molecular chain is 20. Usually, polycarbodiimide is a mixture of molecules of various lengths, and the number of carbodiimide groups is expressed as an average value. Polycarbodiimide, which has the number of carbodiimide groups in the above range and is solid at around room temperature, can be powdered, so that it is excellent in workability and compatibility when mixed with an elastomer, and is also preferable in terms of uniform reactivity and bleed-out resistance. .. The number of carbodiimide groups can be measured, for example, by using a conventional method (a method of dissolving with an amine and performing back titration with hydrochloric acid).

From the viewpoint of stability and handleability, the polycarbodiimide has an isocyanate group at the terminal, and the isocyanate group content is preferably 0.5 to 4% by mass, more preferably 1 to 3% by mass. In particular, polycarbodiimides derived from dicyclohexylmethane diisocyanate or isophorone diisocyanate, which have an isocyanate group content in the above range, are preferable. The isocyanate group content can be measured by using a conventional method (a method of dissolving with amine and performing back titration with hydrochloric acid).

Examples of the isocyanate-based cross-linking agent include the polycarbodiimide compound containing the isocyanate group and the isocyanate compound which is a raw material of the polycarbodiimide compound.

As the acid anhydride-based cross-linking agent, a compound containing 2 to 4 anhydrides per molecule is preferable from the viewpoint of stability and handleability. Examples of such a compound include phthalic acid anhydride, trimellitic acid anhydride, pyromellitic acid anhydride and the like.

The blending (content) amount of the cross-linking agent is appropriately adjusted depending on the extrusion conditions, the desired expansion ratio, etc., but is preferably 0.1 to 4.5 parts by mass, more preferably 0.1 part by mass with respect to 100 parts by mass of the elastomer. It is 0.1 to 4 parts by mass, more preferably 0.1 to 3 parts by mass.

In addition to the antioxidant and the cross-linking agent, various additives can be added to the thermally conductive insulating elastomer composition depending on the purpose. Examples of the additive include light stabilizers such as hindered amine-based, benzotriazole-based, benzophenone-based, benzoate-based, triazole-based, nickel-based, and salicyl-based light stabilizers, lubricants, fillers, flame retardants, flame retardant aids, and mold release agents. Agents, antistatic agents, molecular modifiers such as peroxides, metal deactivators, organic and inorganic nucleating agents, neutralizing agents, antioxidants, antibacterial agents, fluorescent whitening agents, organic and inorganic Examples thereof include based pigments, organic and inorganic phosphorus compounds used for the purpose of imparting flame retardancy and thermal stability. When the additive is blended, the content (total content when a plurality of additives are used) is preferably 30% by mass or less, more preferably 20 in the thermally conductive insulating elastomer composition. It is 0% by mass or less, more preferably 10% by mass or less, and particularly preferably 5% by mass or less.

<Thermal Conductive Insulating Elastomer Composition>
The method for producing the thermally conductive insulating elastomer composition of the present invention is not particularly limited, and can be produced by mixing the above components. In the present invention, the inorganic filler and the triazinedithiol-based compound are brought into contact with each other from the viewpoint of enhancing the dispersibility of the inorganic filler in the composition and facilitating the formation of a continuum formed by connecting the inorganic fillers. Then, the triazinedithiol-based compound is adhered to the surface of the inorganic filler to obtain a surface-modified inorganic filler, and then the obtained surface-modified inorganic filler is dispersed in the elastomer to obtain a thermally conductive insulating elastomer composition. It is preferable to manufacture.

The method of contacting the inorganic filler with the triazinedithiol-based compound is not particularly limited, and for example, a method of mixing the inorganic filler with the triazinedithiol-based compound, a solution in which the triazinedithiol-based compound is dissolved in a solvent, or a solution of the triazinedithiol-based compound. Examples thereof include a method in which the inorganic filler is immersed in a dispersion liquid in which the triazinedithiol-based compound is dispersed in a solvent, the inorganic filler is taken out, and then the inorganic filler is dried.

<Thermal conductive insulating elastomer molded product>
The thermally conductive insulating elastomer molded product of the present invention can be obtained by molding the thermally conductive insulating elastomer composition. The method for producing the thermally conductive insulating elastomer molded product is not particularly limited, but it is preferable to press and / or heat the thermally conductive insulating elastomer composition for molding. Examples of the molding method include an extrusion molding method, a mold molding method, and a hot press method. The temperature and pressure at the time of molding are appropriately adjusted according to the type of elastomer used.

The shape of the thermally conductive insulating elastomer molded product can be appropriately selected depending on the intended use, and examples thereof include a sheet shape, a plate shape, a film shape, and a block shape.

Hereinafter, the present invention will be described in more detail with reference to Examples and Comparative Examples, but the present invention is not limited thereto, and can be appropriately modified and carried out to the extent that it can be applied to the above-mentioned and the purposes described below. And all of them are included in the technical scope of the present invention.

Production Example 1
(Production of triazinedithiol-based compound represented by the following formula (7))

17.72 g (0.1 mol) of triazine trithiol and 0.102 mol of 3-triethoxysilylpropylamine were added to 100 mL of toluene to give a mixture. Here, triazine trithiol is dispersed in toluene, and 3-triethoxysilylpropylamine is dissolved in toluene. Then, the mixture was stirred at 140 ° C. for 30 minutes to allow the reaction to proceed. After completion of the reaction, toluene was distilled off under reduced pressure and recovered, and the gas component was absorbed in a 20% NaOH aqueous solution to remove the generated hydrogen sulfide. The obtained solid was washed with ethyl ether to remove a trace amount of unreacted amine, and a crude triazinedithiol-based compound was obtained in a yield of 96% or more. Then, the crude triazinedithiol-based compound was recrystallized from isopropanol and purified to obtain a triazinedithiol-based compound represented by the above formula (7). The melting point of the triazinedithiol-based compound after recrystallization was 235 to 236 ° C., and the elemental analysis values were C: 40.2%, N: 16.0%, and S: 18.2%. A melting point measuring instrument manufactured by Mita Riken Kogyo Co., Ltd. was used for melting point analysis. A Yanagimoto CHN coder was used for carbon and nitrogen analysis, and a CHN coder manufactured by Parkin Elma was used for sulfur analysis.

Manufacturing example 2
(Manufacturing of surface-modified aluminum nitride filler (B1))
The triazine-dithiol-based compound produced in Production Example 1 was dissolved in ion-exchanged water to obtain an aqueous solution containing 0.1 wt% of the triazine-dithiol-based compound. Then, 100 g of the aluminum nitride filler (FAN-05 manufactured by Furukawa Denshi Co., Ltd.) was immersed in the aqueous solution for 10 minutes, then taken out and dried at 100 ° C. for 60 minutes to obtain the surface-modified aluminum nitride filler (B1). Obtained.

Production example 3
(Manufacturing of surface-modified boron nitride filler (B2))
The triazine-dithiol-based compound produced in Production Example 1 was dissolved in ion-exchanged water to obtain an aqueous solution containing 0.1 wt% of the triazine-dithiol-based compound. Then, 100 g of the boron nitride filler (SP-2 manufactured by Denka Co., Ltd.) was immersed in the aqueous solution for 10 minutes, then taken out and dried at 100 ° C. for 60 minutes to obtain a surface-modified boron nitride filler (B2). rice field.

Example 1
(Manufacturing of Thermally Conductive Insulating Elastomer Composition)
After mixing 60 parts by mass of dimethylpolysiloxane (A1) sealed at both ends with a dimethylvinyl group having an average degree of polymerization of 8000 and 40 parts by mass of a surface-modified aluminum nitride filler (B1), 150 parts of the obtained mixture was mixed. It was put into a tabletop kneader (Laboplast Mill 20C200) manufactured by Toyo Seiki Co., Ltd. preheated to ° C. and kneaded at 40 rpm for 10 minutes to obtain a thermally conductive insulating elastomer composition.

Example 2
(Manufacturing of Thermally Conductive Insulating Elastomer Composition)
A mixture of 50 parts by mass of dimethylpolysiloxane (A1) sealed at both ends with a dimethylvinyl group having an average degree of polymerization of 8000, 10 parts by mass of 2-methylbenzoyl peroxide, and 40 parts by mass of a surface-modified boron nitride filler (B2). Then, the obtained mixture was put into a tabletop kneader (Laboplast Mill 20C200) manufactured by Toyo Seiki Co., Ltd. preheated to 150 ° C. and kneaded at 40 rpm for 10 minutes to obtain a thermally conductive insulating elastomer composition. rice field.

Example 3
(Manufacturing of Thermally Conductive Insulating Elastomer Composition)
After mixing 50 parts by mass of dimethylpolysiloxane (A1) sealed at both ends with a dimethylvinyl group having an average degree of polymerization of 8000 and 2 parts by mass of a surface-modified aluminum nitride filler (B1), 150 parts of the obtained mixture was mixed. The mixture was placed in a tabletop kneader (Laboplast Mill 20C200) manufactured by Toyo Seiki Co., Ltd. preheated to ° C. and kneaded at 40 rpm for 10 minutes. After taking out the obtained kneaded product, it is cut into chips, the obtained chips and 48 parts by mass of the alumina filler are mixed, and then kneaded again at 40 rpm for 10 minutes to obtain a thermally conductive insulating elastomer composition. Manufactured.

Examples 4, 5, and 8
(Manufacturing of Thermally Conductive Insulating Elastomer Composition)
A thermally conductive insulating elastomer composition was produced by the same method as in Example 3 except that the types and blending amounts of the silicone-based elastomer and the filler were changed as shown in Table 1.

Example 6
(Manufacturing of Thermally Conductive Insulating Elastomer Composition)
Obtained after mixing 40 parts by mass of Shin-Etsu Silicone KE-541-U (manufactured by Shin-Etsu Chemical Co., Ltd.) (A3), 10 parts by mass of 2-methylbenzoyl peroxide, and 2 parts by mass of a surface-modified boron nitride filler (B2). The mixture was put into a tabletop kneader (Laboplast Mill 20C200) manufactured by Toyo Seiki Co., Ltd. preheated to 150 ° C., and kneaded at 40 rpm for 10 minutes. After taking out the obtained kneaded product, it is cut into chips, the obtained chips and 48 parts by mass of the alumina filler are mixed, and then kneaded again at 40 rpm for 10 minutes to obtain a thermally conductive insulating elastomer composition. Manufactured.

Example 7
(Manufacturing of Thermally Conductive Insulating Elastomer Composition)
A thermally conductive insulating elastomer composition was produced in the same manner as in Example 6 except that the type of the filler was changed as shown in Table 1.

Comparative Examples 1 to 4
(Manufacturing of Thermally Conductive Insulating Elastomer Composition)
A thermally conductive insulating elastomer composition was produced in the same manner as in Example 1 except that the types and blending amounts of the silicone-based elastomer and the filler were changed as shown in Table 1.

〔Evaluation method〕
Thermal conductivity, heat resistance, moisture heat resistance, thermal resistance, and dielectric breakdown voltage were evaluated by the following methods.
(Preparation of evaluation sheet sample)
The evaluation sheet sample was prepared using a heat press machine (SA-302-I manufactured by Tester Sangyo Co., Ltd.). The thermally conductive insulating elastomer compositions prepared in Examples and Comparative Examples were placed in a mold having a predetermined thickness and melted for 2 minutes at a temperature condition of the melting point of the silicone-based elastomer + 20 ° C. A load of 100 kgf / cm ² was applied to the obtained melt, and after 1 minute, the melt was soaked in water and rapidly cooled to obtain an evaluation sheet sample having a predetermined thickness.

(Measurement of thermal conductivity)
The specific heat was measured using DSC2920 manufactured by TA Instruments Co., Ltd. 10.0 mg of the thermally conductive insulating elastomer composition (sample) prepared in Examples and Comparative Examples was placed in an aluminum pan, and the temperature was raised from room temperature to 200 ° C. at a heating temperature of 10 ° C./min to reach 200 ° C. Was held for 5 minutes. Then, the temperature was lowered at 10 ° C./min. Similarly, 26.8 mg of sapphire as a reference substance was placed in an aluminum pan and measured under the same conditions. Furthermore, an empty aluminum pan containing no sample as a blank was measured under the same conditions. The value of Heat Flow at 23 ° C. of each DSC curve was read, and the specific heat capacity was calculated by the following formula.

Cp = (h / H) x (m'/ m) x C'p

Cp: Specific heat of the sample C'p: Specific heat of the reference material (sapphire) at 23 ° C. h: Difference between the DSC curve of the blank and the sample H: Difference between the DSC curves of the blank and the reference material (sapphire) m: Mass of the sample (g) )
m': Mass (g) of reference substance (sapphire)

The specific gravity was measured using an automatic hydrometer DH100 manufactured by Toyo Seiki Co., Ltd. The prepared evaluation sheet sample was heat-pressed to obtain a sheet having a thickness of 0.5 mm. Then, the sheet was cut into a size of 10 mm × 10 mm to obtain a sample for specific gravity measurement. Using the prepared sample for specific gravity measurement, the specific gravity was measured by the underwater substitution method.
The thermal diffusivity was measured using a thermal diffusivity coefficient measuring device ai-phase Mobile 1 manufactured by iPhase Co., Ltd. The prepared evaluation sheet sample was heat-pressed to obtain a sheet having a thickness of 0.5 mm. The thermal diffusivity in the thickness direction was measured using the prepared sheet.
Then, the thermal conductivity was calculated by the following formula from the specific heat, specific gravity, and thermal diffusivity obtained by the above method.

Thermal conductivity (W / m · K) = specific gravity x specific heat (J / g · K) x thermal diffusivity (m ² / sec)

(Evaluation of heat resistance)
The prepared evaluation sheet sample was heat-pressed to obtain a sheet having a thickness of 1 mm. Then, the sheet was cut into a size of 10 mm × 50 mm to obtain a sample for heat resistance evaluation. A sample for heat resistance evaluation was put into a constant temperature bath, and after 1000 hours had passed at a temperature of 85 ° C., the tensile elongation was measured, and the temperature which became 50% of the initial value was examined. Then, it was evaluated according to the following criteria. The higher the temperature, which is 50% of the initial value, the higher the heat resistance.
⊚: 160 ° C or higher ○: 130 ° C or higher and lower than 160 ° C Δ: 110 ° C or higher and lower than 130 ° C ×: less than 110 ° C

(Evaluation of moisture resistance)
The prepared evaluation sheet sample was heat-pressed to obtain a sheet having a thickness of 1 mm. Then, the sheet was cut into a size of 10 mm × 50 mm to obtain a sample for evaluation of moisture resistance and heat resistance. The sample for evaluation of moisture resistance and heat resistance was put into a constant temperature and humidity chamber, and the expansion coefficient of the sample was observed under the condition of 85 ° C. × 85% Rh. The length, width, and thickness (mm) of the sample before and after 1000 hours of charging into the constant temperature and humidity chamber were measured, and the expansion coefficient (%) in each direction was calculated. Furthermore, the product was taken and the coefficient of thermal expansion (%) was calculated. At this time, the expansion coefficient before the constant temperature and humidity chamber is set to 100%. A constant pressure caliper was used for the measurement. The smaller the coefficient of thermal expansion, the more preferable. When the coefficient of thermal expansion is 110% or less, the deterioration of brittleness is small and good. If the coefficient of thermal expansion exceeds 110%, the brittleness deteriorates, so that it is not preferable to use it under high humidity.

(Measurement of thermal resistance)
The prepared evaluation sheet sample was heat-pressed to obtain a sheet having a thickness of 0.3 mm. The thermal resistance of the sheet was measured according to ASTM D5470. The thermal resistance is preferably 0.6 × 10 e ^-3 (m ² K / W) or less. The thermal resistance is almost proportional to the thickness of the sheet.

(Measurement of dielectric breakdown voltage)
The prepared evaluation sheet sample was heat-pressed to obtain a sheet having a thickness of 0.1 mm. The breakdown voltage of the sheet was measured according to JIS K6249. The dielectric breakdown voltage is preferably 3 kV or more. The breakdown voltage is almost proportional to the thickness of the sheet.

The compounds in Table 1 are as follows.
A1: Didimethylpolysiloxane with an average degree of polymerization of 8000 and sealed at both ends with a dimethylvinyl group A2: Didimethylpolysiloxane with an average degree of polymerization of 10,000 and sealed at both ends with a dimethylvinyl group A3: Shinetsu Silicone KE- 541-U (manufactured by Shin-Etsu Chemical Industry Co., Ltd.)
B1: Surface-modified aluminum nitride filler produced in Production Example 2 B2: Surface-modified boron nitride filler produced in Production Example 3

The thermally conductive insulating elastomer molded body of the present invention is useful as a material for automobile members and members such as electronic circuit boards that are required to have insulation and heat dissipation.

Claims (9)

A thermally conductive insulating elastomer composition containing at least one elastomer selected from the group consisting of a silicone-based elastomer and a fluorine-based elastomer, an inorganic filler, and a triazinedithiol-based compound represented by the following general formula (1).

(In the formula, M ¹ and M ² are independently H, Li, Na, K, or Cs, R ¹ is S, O, or NR ³ , and R ³ is H, or an alkyl group, halogenated. Alkyl group, hydroxyalkyl group, alkoxyalkyl group, alkenyl group, halogenated alkenyl group, hydroxyalkenyl group, alkoxyalkenyl group, phenyl group, halogenated phenyl group, hydroxyphenyl group, alkoxyphenyl group, biphenyl group, halogenated biphenyl group , Hydroxybiphenyl group, alkoxybiphenyl group, naphthyl group, naphthyl halide group, hydroxynaphthyl group, alkoxynaphthyl group, carboxyl group, ester group, urethane group, azo group, cyano group, amino group, amide group, and alkoxysilyl group. It is an organic group having at least one functional group selected from the group consisting of, R ² is the same as the organic group, or NR ³ and R ² form a heterocycle). The thermally conductive insulating elastomer composition according to claim 1, wherein the triazinedithiol-based compound is at least one of the triazinedithiol-based compounds represented by the following general formulas (2) to (4).

(In the formula, M ¹ , M ² , R ² and R ³ are the same as above.)

(In the formula, M ¹ and M ² are the same as described above, and R ¹ is S, O, -NHCH ₂ CH ₂ O-, -N (CH ₃ ) CH ₂ CH ₂ O-, -N (C ₃ H). ₇ ) CH ₂ CH ₂ O-, -NHCH ₂ CH ₂ CH ₂ CH ₂ O-, -N (C ₂ H ₅ ) CH ₂ CH ₂ CH ₂ CH ₂ O-, -NHCH ₂ (CH ₂ ) ₈ CH ₂ O-, -NHCH ₂ CH (CH ₃ ) O-, -NHC ₆ H ₄ O-, -N (C ₂ H ₅ ) C ₆ H ₄ O-, -NHC ₁₀ H ₆ O-, -N (CH ₂ ) CH ₂ ) ₂ CHO-, -N (CH ₂ CH ₂ ) ₂ NCH ₂ CH ₂ O-, -N (CH ₂ CH ₂ OH) CH ₂ CH ₂ O-, -N (CH ₂ CH ₂ CH ₂ OH) CH ₂ CH ₂ CH ₂ O-, -N (CH ₂ CH (CH ₃ ) OH) CH ₂ CH (CH ₃ ) O-, -N (CH ₂ CH ₂ CH ₂ CH ₂ OH) CH ₂ CH ₂ CH ₂ CH ₂ O-, -NHCH ₂ C ₆ H ₄ O-, -NHC ₆ H ₁₁ O-, or -N (C ₃ H ₇ ) C ₆ H ₄ O-, where R ⁴ is an alkylene group and R ⁵ is an alkoxy group, and R ⁶ and R ⁷ are independently alkoxy groups or alkyl groups, respectively.)

(In the formula, M ¹ , M ² and R ⁵ to R ⁷ are the same as above, R ⁸ is a hydrogen or alkyl group, R ⁹ is an alkylene or alkylene oxy group, R ⁸ and R ⁹ May combine with each other to form a ring.) The heat conductive insulating elastomer composition according to claim 1 or 2, wherein the inorganic filler contains at least one selected from the group consisting of an aluminum nitride filler and a boron nitride filler. The heat conductive insulating elastomer composition according to any one of claims 1 to 3, wherein the content of the inorganic filler is 20 to 400 parts by mass with respect to 100 parts by mass of the elastomer. The thermally conductive insulating elastomer composition according to any one of claims 1 to 4, wherein the content of the triazinedithiol-based compound is 5 × 10 ^-7 to 5 parts by mass with respect to 100 parts by mass of the inorganic filler. A thermally conductive insulating elastomer molded product obtained from the thermally conductive insulating elastomer composition according to any one of claims 1 to 5. The heat conductive insulating elastomer molded body according to claim 6, wherein the heat conductive insulating elastomer molded body is a heat conductive insulating elastomer sheet. The method for producing a thermally conductive insulating elastomer molded product according to claim 6 or 7, wherein the inorganic filler is brought into contact with the triazinedithiol-based compound, and the triazinedithiol-based compound is adhered to the surface of the inorganic filler. Step A to obtain the surface-modified inorganic filler, step B to obtain the thermally conductive insulating elastomer composition by dispersing the surface-modified inorganic filler in the elastomer, and a step of molding the thermally conductive insulating elastomer composition. A method for producing a thermally conductive insulating elastomer molded product containing C. The method for producing a thermally conductive insulating elastomer molded product according to claim 8, wherein in the step C, the thermally conductive insulating elastomer composition is pressurized and / or heated to be molded.