Thermally conductive silicone adhesive composition and method for producing a thermally conductive silicone adhesive composition

Abstract

To provide a thermally conductive silicone adhesive composition that does not require high-temperature curing and exhibits sufficient adhesion to metals and resins, etc. [Solution] The above problem can be solved, for example, with a thermally conductive silicone adhesive composition, (A) An organopolysiloxane having a viscosity of 500 mPa·s or more and 1,000,000 mPa·s or less at 25°C, and having at least two alkenyl groups in one molecule, (B) An organopolysiloxane having at least two hydrosilyl groups and at least one aromatic group in one molecule, (C) A non-silicone organic compound having at least one alkenyl group and at least one aromatic ring in one molecule, (D) Addition reaction catalyst, (E) Thermally conductive filler, This is solved by a thermally conductive silicone adhesive composition containing [the specified element].

Description

[Technical Field]

[0001] The present invention relates to a thermally conductive silicone adhesive composition and a method for producing a thermally conductive silicone adhesive composition, etc. [Background technology]

[0002] In equipment or devices that require continuous heat dissipation, the adhesive used must also have high thermal conductivity. This is because even if components with high heat dissipation properties are used, if the adhesive has low thermal conductivity, heat transfer from component to component will be hindered. Conventionally, various adhesives with thermal conductivity have been developed. For example, Japanese Patent Publication No. 2012-067153 and Japanese Patent Publication No. 2015-093970 disclose thermally conductive silicone adhesive compositions comprising compositions containing specific organopolysiloxanes. [Prior art documents] [Patent Documents]

[0003] [Patent Document 1] Japanese Patent Publication No. 2012-067153 [Patent Document 2] Japanese Patent Publication No. 2015-093970 [Overview of the Initiative] [Problems that the invention aims to solve]

[0004] Conventional thermally conductive silicone adhesive compositions require high-temperature heat curing to exhibit adhesive strength. Such adhesive compositions can be used without problems for bonding components with a certain degree of heat resistance, such as semiconductor devices. However, high-temperature heat curing is not possible when bonding components such as battery cells or electronic components with low heat resistance. In view of the above, the present invention relates to providing a novel thermally conductive silicone adhesive composition that does not require high-temperature heat curing and exhibits sufficient adhesion to metals and resins. [Means for Solving the Problem]

[0005] The thermally conductive silicone adhesive composition according to one aspect of the present invention is: (A) an organopolysiloxane having a viscosity at 25°C of 500 mPa·s or more and 1,000,000 mPa·s or less, and having at least two alkenyl groups per molecule; (B) an organopolysiloxane having at least two hydrosilyl groups per molecule and at least one aromatic group per molecule; (C) a non-silicone organic compound having at least one alkenyl group per molecule and at least one aromatic ring per molecule; (D) an addition reaction catalyst; and (E) a thermally conductive filler, wherein when the total amount of the component (A), the component (B), and the component (C) is 100 parts by mass, the content of the component (A) is 65 parts by mass or more and 95 parts by mass or less, the content of the component (B) is 3 parts by mass or more and 15 parts by mass or less, the content of the component (C) is 1 part by mass or more and 25 parts by mass or less, and the content of the component (E) is 40 parts by mass or more and 300 parts by mass or less.

[0006] The two-component thermally conductive silicone adhesive according to one aspect of the present invention has a first liquid and a second liquid that are separately packaged from each other, and comprises: (A) an organopolysiloxane having a viscosity at 25°C of 500 mPa·s or more and 1,000,000 mPa·s or less, and having at least two alkenyl groups per molecule; (B) an organopolysiloxane having at least two hydrosilyl groups per molecule and at least one aromatic group per molecule; (C) a non-silicone organic compound having at least one alkenyl group per molecule and at least one aromatic ring per molecule; (D) an addition reaction catalyst; and (E) comprising a thermally conductive filler, When the total amount of component (A), component (B), and component (C) in the entire two-component thermal conductive silicone adhesive is 100 parts by mass, The content of component (A) is 65 parts by mass or more and 95 parts by mass or less, The content of component (B) is 3 parts by mass or more and 15 parts by mass or less, The content of component (C) is 1 part by mass or more and 25 parts by mass or less, The content of component (E) is 40 parts by mass or more and 300 parts by mass or less. If component (B) is included in the first liquid, component (D) is not included in the first liquid, and if component (B) is included in the second liquid, component (D) is not included in the second liquid.

[0007] A method for producing a thermally conductive silicone adhesive composition according to one aspect of the present invention comprises the step of mixing the first liquid and the second liquid of the two-component thermally conductive silicone adhesive.

[0008] A method for manufacturing an electrical device, electrical component, electronic device, electronic component, or power supply device according to one aspect of the present invention includes a step of interposing the thermally conductive silicone adhesive composition between a first substrate and a second substrate, and fixing the first substrate and the second substrate to each other by curing the thermally conductive silicone adhesive composition, wherein the curing in the step is performed at 50°C or below. [Effects of the Invention]

[0009] The present invention provides a thermally conductive silicone adhesive composition that does not require heat curing at high temperatures and exhibits sufficient adhesion to metals and resins. [Modes for carrying out the invention]

[0010] Electric vehicle batteries have a structure in which multiple battery cells are housed in a case. The surface of the battery cells is typically covered with polycarbonate or polyethylene terephthalate, with some aluminum exposed. The surface of the case may be made of iron electrodeposited with aluminum or epoxy resin. Therefore, it is desirable that the adhesive composition for fixing these together has sufficient adhesion to at least polycarbonate, polyethylene terephthalate, epoxy resin, and aluminum. The inventors have found that the thermally conductive silicone adhesive composition described below can exhibit sufficient adhesion even for such applications. In particular, the thermally conductive silicone adhesive composition described below has sufficient adhesion even to polycarbonate, which is known to be a difficult-to-bond resin. Furthermore, the thermally conductive silicone adhesive composition described below can be cured at low temperatures and has moderate fluidity and high thermal conductivity.

[0011] [Definition] Unless otherwise specified, the tests, experiments, and measurements described herein were conducted at room temperature (25°C) and normal pressure (atmospheric pressure). Unless otherwise specified, the physical properties described herein are values ​​measured at room temperature (25°C) and normal pressure (atmospheric pressure). Unless otherwise specified, the notation "A~B" indicating a numerical range in this specification shall be interpreted as a range of values ​​including the lower limit A and the upper limit B, i.e., "A or greater and B or less". Unless otherwise specified, the viscosity described herein is a value measured in accordance with JIS K7117-2 at a temperature of 25°C and a shear rate of 10 / s.

[0012] [Thermally conductive silicone adhesive composition] A thermally conductive silicone adhesive composition according to one aspect of the present invention, (A) An organopolysiloxane having a viscosity of 500 mPa·s or more and 1,000,000 mPa·s or less at 25°C, and having at least two alkenyl groups in one molecule, (B) An organopolysiloxane having at least two hydrosilyl groups and at least one aromatic group in one molecule, (C) A non-silicone organic compound having at least one alkenyl group and at least one aromatic ring in one molecule, (D) Addition reaction catalyst, (E) comprising a thermally conductive filler, When the total amount of component (A), component (B), and component (C) is 100 parts by mass, The content of component (A) is 65 parts by mass or more and 95 parts by mass or less, The content of component (B) is 3 parts by mass or more and 15 parts by mass or less, The content of component (C) is 1 part by mass or more and 25 parts by mass or less, The content of component (E) is 40 parts by mass or more and 300 parts by mass or less.

[0013] (Component A) Component (A) is the main component of the thermally conductive silicone adhesive composition and is an organopolysiloxane having at least two alkenyl groups in one molecule. Preferably, component (A) is an organopolysiloxane having at least two alkenyl groups directly bonded to silicon atoms in one molecule. Component (A) may be a single organopolysiloxane or a combination of multiple organopolysiloxanes.

[0014] The molecular structure of component (A) is not particularly limited. Component (A) may be a polymer consisting of a single siloxane unit or a copolymer consisting of two or more siloxane units. Component (A) may have, for example, a linear structure, a partially branched linear structure, a branched linear structure, a cyclic structure, or a branched cyclic structure. Component (A) is preferably substantially a linear organopolysiloxane. Specifically, component (A) may be a linear diorganopolysiloxane in which the molecular chain mainly consists of repeating diorganosiloxane units and both ends of the molecular chain are sealed with triorganosiloxy groups. Component (A) may have silanol groups on some or all of the ends of the molecular chain or on some of the side chains.

[0015] (A) The position of the alkenyl group in component is not particularly limited. The alkenyl group may be bonded to only one of the silicon atoms at the end of the molecular chain or to only one of the silicon atoms at the non-terminus (middle of the molecular chain), or to both.

[0016] In one embodiment, component (A) may be an organopolysiloxane having one alkenyl group at each end of the molecular chain. Using an organopolysiloxane having one alkenyl group at each end of the molecular chain allows for the uniform formation of crosslinking sites in the hydrosilylation reaction with component (B) described later, making it easier to obtain a strong yet flexible network structure. Furthermore, it is easier to suppress excessive crosslinking reactions or self-condensation, enabling a stable curing reaction.

[0017] Furthermore, in another embodiment, component (A) may be an organopolysiloxane having alkenyl groups not only at both ends of the molecular chain but also at the non-terminus (part of the molecular chain). Using an organopolysiloxane having alkenyl groups not only at both ends of the molecular chain but also at the non-terminus ensures a large number of crosslinking sites in the hydrosilylation reaction with component (B) described later, making it possible to increase the hardness of the cured product regardless of the molecular weight of the organopolysiloxane. In addition, since the reaction endpoint is reached earlier due to the large number of crosslinking sites, the curing time can also be shortened.

[0018] The number of alkenyl groups in one molecule of component (A) can be appropriately determined according to the required hardness of the cured product and the molecular weight of component (A). The number of alkenyl groups in one molecule should be two or more, preferably two to 50, more preferably two to 20, even more preferably two to 5, particularly preferably two, and most preferably having one alkenyl group at each end of the molecular chain (a total of two).

[0019] Component (A) has a viscosity at 25°C of 500 mPa·s or more and 1,000,000 mPa·s or less. The viscosity of component (A) at 25°C may be 800 mPa·s or more and 700,000 mPa·s or less, 1,000 mPa·s or more and 500,000 mPa·s or less, 2,000 mPa·s or more and 200,000 mPa·s or less, 5,000 mPa·s or more and 100,000 mPa·s or less, 10,000 mPa·s or more and 50,000 mPa·s or less, or 15,000 mPa·s or more and 30,000 mPa·s or less. By having a viscosity of component (A) at 25°C within an appropriate range, the fluidity of the adhesive composition before curing is adequately ensured. Furthermore, when using a combination of multiple organopolysiloxanes as component (A), the viscosity mentioned above is the value measured using the entire combination of component (A). Therefore, the fluidity (mixed viscosity) of the adhesive composition before curing may be adjusted by mixing two or more organopolysiloxanes with different molecular weights.

[0020] Specifically, component (A) may be represented by the following average empirical formula (1). R 1 a SiO (4-a) / 2 (1) (In formula (1), R 1(These are unsubstituted or substituted monovalent hydrocarbon groups having 1 to 18 carbon atoms, which are either identical or different from each other, and a is, for example, 1.7 to 2.1, preferably 1.8 to 2.5, and more preferably 1.95 to 2.05.)

[0021] In one embodiment, the above R 1 Of the monovalent hydrocarbon groups represented by , at least two are selected from alkenyl groups such as vinyl, allyl, propenyl, isopropenyl, butenyl, isobutenyl, hexenyl, and cyclohexenyl groups, and the remaining groups are substituted or unsubstituted monovalent hydrocarbon groups having 1 to 18 carbon atoms, specifically alkyl groups such as methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, pentyl, neopentyl, hexyl, 2-ethylhexyl, heptyl, octyl, nonyl, decyl, and dodecyl groups; cyclopentyl The following are selected from cycloalkyl groups such as chloromethyl, cyclohexyl, and cycloheptyl groups; aryl groups such as phenyl, tolyl, xylyl, biphenyl, and naphthyl groups; aralkyl groups such as benzyl, phenylethyl, phenylpropyl, and methylbenzyl groups; and groups in which some or all of the hydrogen atoms in these hydrocarbon groups are substituted with halogen atoms, cyano groups, etc. (for example, halogen-substituted alkyl groups or cyano-substituted alkyl groups such as chloromethyl, 2-bromoethyl, 3,3,3-trifluoropropyl, 3-chloropropyl, and cyanoethyl groups).

[0022] The above R 1 Of the monovalent hydrocarbon groups represented by , the alkenyl groups that are required in quantities of two or more per molecule are preferably vinyl, allyl, propenyl, isopropenyl, 2-methyl-1-propenyl, 2-methylallyl, and 2-butenyl groups, with vinyl being particularly preferred. 1 The methyl group and the phenyl group are preferred, with the methyl group being particularly preferred. Also, the total R contained in component (A) 1It is preferable that 70 mol% or more of the groups in [the structure] are methyl groups from the viewpoints of physical properties of the cured product and economic efficiency. In one embodiment, as component (A), all R 1 in which 80 mol% or more of the groups are methyl groups are used.

[0023] The molecular structure of component (A) includes dimethylpolysiloxane endblocked with dimethylvinylsiloxy groups at both molecular chain terminals, dimethylsiloxane-methylphenylsiloxane copolymer endblocked with dimethylvinylsiloxy groups at both molecular chain terminals, dimethylsiloxane-methylvinylsiloxane copolymer endblocked with dimethylvinylsiloxy groups at both molecular chain terminals, dimethylsiloxane-methylvinylsiloxane-methylphenylsiloxane copolymer endblocked with dimethylvinylsiloxy groups at both molecular chain terminals, dimethylsiloxane-methylvinylsiloxane copolymer endblocked with trimethylsiloxy groups at both molecular chain terminals, siloxane units represented by formula: (CH3)2ViSiO 1 / 2 , siloxane units represented by formula: (CH3)3SiO 1 / 2 , organopolysiloxanes consisting of siloxane units represented by formula: SiO 4 / 2 (wherein Vi in the formula represents a vinyl group), organopolysiloxanes obtained by substituting part or all of methyl groups of these organopolysiloxanes with alkyl groups such as ethyl group and propyl group; aryl groups such as phenyl group and tolyl group; halogenated alkyl groups such as 3,3,3-trifluoropropyl group, and mixtures of two or more of these organopolysiloxanes are exemplified. Among them, linear diorganopolysiloxanes having vinyl groups at both terminals of the molecular chain are preferable from the viewpoint of facilitating reaction control.

[0024] Commercially available products may be used as these organopolysiloxanes, or products produced by methods known to those skilled in the art may be used.

[0025] When the total amount of components (A), (B), and (C) is 100 parts by mass, the content of organopolysiloxane, which is component (A), is 65 parts by mass or more and 95 parts by mass or less, and may be 70 parts by mass or more and 90 parts by mass or less, 75 parts by mass or more and 85 parts by mass or less, or 80 parts by mass or more and 83 parts by mass or less. By having an appropriate content of organopolysiloxane, which is component (A), the fluidity of the thermally conductive silicone adhesive composition before curing is adequately ensured.

[0026] ((B) component) Component (B) is an organopolysiloxane having at least two hydrosilyl groups (Si-H groups) and at least one aromatic group per molecule. Component (B) acts as a crosslinking agent for curing the thermally conductive silicone adhesive composition by the reaction of its hydrosilyl groups with the carbon-carbon double bonds of other components (hydrosilylation reaction). Furthermore, the presence of at least one aromatic group in component (B) per molecule improves its compatibility with component (C), described later, making it easier for component (C) to bond with component (B). Component (B) may be a single organopolysiloxane or a combination of multiple organopolysiloxanes.

[0027] The position of the hydrosilyl group in component (B) is not particularly limited. The hydrosilyl group may be located at the end of the molecular chain, at the end of the molecular chain (in the middle of the molecular chain), or at both. An organopolysiloxane having a hydrosilyl group only at the end of the molecular chain and an organopolysiloxane having a hydrosilyl group only at the end of the molecular chain may be used in combination.

[0028] The number of hydrosilyl groups in one molecule of component (B) is not particularly limited as long as there are two or more. The number of hydrosilyl groups in one molecule of component (B) may be two or more and 50 or less, four or more and 40 or less, six or more and 30 or less, or eight or more and 20 or less.

[0029] (B) The position of the aromatic group in component (B) is not particularly limited. In this specification, "aromatic group" means a group obtained by removing one hydrogen atom from an aromatic ring of an aromatic compound. In this specification, "aromatic ring" means a cyclic structure having a conjugated delocalized π-electron system, where the π electrons contained in the π-electron system satisfy Hückel's rule. The cyclic structure may be a monocyclic or a fused polycyclic, and in addition to carbon atoms, or instead of carbon atoms, heteroatoms such as nitrogen atoms, oxygen atoms, and sulfur atoms may constitute at least part of the ring. However, it is preferable that the cyclic structure does not have heteroatoms constituting part of the ring. The aromatic group may be directly bonded to the silicon atoms of the organopolysiloxane skeleton, or it may be bonded via a linker such as a divalent hydrocarbon group (preferably an alkylene group) having 1 to 10 carbon atoms or a divalent polyoxyalkylene group having 1 to 10 carbon atoms. It is preferable that the aromatic group is directly bonded to the silicon atoms of the organopolysiloxane skeleton. Aromatic groups include, for example, phenyl, tolyl, xyl, mesityl, cumenyl, naphthyl, and anthyl groups. 6~30 Aromatic hydrocarbon groups; such as pyridyl, pyrazolyl, thienyl, furyl, indolyl, and quinolyl groups. 4~20 Examples include heterocyclic aromatic groups. These groups may be substituted with one or more halogen atoms, hydroxyl groups, nitro groups, cyano groups, alkoxy groups, etc. Aromatic groups include C 6~30 Aromatic hydrocarbon groups are preferred, phenyl groups, tolyl groups, or xylyl groups are more preferred, and phenyl groups are particularly preferred.

[0030] Aromatic groups may be located at the ends of the molecular chain, at the ends of the molecular chain (in the middle of the molecular chain), or in both locations. It is preferable that aromatic groups be located at the ends of the molecular chain (in the middle of the molecular chain).

[0031] The number of aromatic groups in one molecule of component (B) is not particularly limited, as long as there is one or more. The number of aromatic groups in one molecule of component (B) may be one to 20, or two to 10. By setting the number of aromatic groups in one molecule of component (B) within an appropriate range, the compatibility with component (C), described later, is improved, component (C) becomes easier to bond with component (B), and consequently the adhesiveness of the thermal conductive silicone adhesive composition is further improved. That is, because of the high compatibility between component (A) and component (B), between component (B) and component (C), and between component (C) and the adherend, component (B) crosslinks with component (A) and component (C), increasing the compatibility of the entire thermal conductive silicone adhesive composition with respect to the adherend, and further improving the adhesiveness of the thermal conductive silicone adhesive composition.

[0032] (B) The number of hydrosilyl groups in one molecule of component B H The number of aromatic groups in one molecule of component (B) is B Ar Therefore, B Ar / B H The value of is, for example, within the range of 0.05 or more and 1 or less, preferably within the range of 0.1 or more and 0.5 or less, and more preferably within the range of 0.15 or more and 0.4 or less. Ar / B H By setting the value within an appropriate range, the balance between curability and adhesion of the thermally conductive silicone adhesive composition is further improved.

[0033] Component (B) may have, for example, a linear structure, a partially branched linear structure, a branched linear structure, a cyclic structure, a branched cyclic structure, or a three-dimensional network structure. In one embodiment, component (B) is not a cyclic organopolysiloxane. Specifically, component (B) may be represented by the following average composition formula (2). R 2 p H q Ar r SiO (4-p-q-r) / 2 (2) (In the formula, R 2(i.e., q and r are identical or different unsubstituted or substituted monovalent hydrocarbon groups having 1 to 10 carbon atoms (excluding alkenyl and aromatic groups), Ar is an aromatic group, p is, for example, 0 to 3.0, preferably 0.7 to 2.1, q is, for example, 0.0001 to 3.0, preferably 0.001 to 1.0, r is, for example, 0.0001 to 3.0, preferably 0.001 to 1.0, and p + q + r is a positive number satisfying, for example, 0.5 to 3.0, preferably 0.8 to 3.0.)

[0034] R in equation (2) 2 These are selected from alkyl groups such as methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, pentyl, neopentyl, hexyl, 2-ethylhexyl, heptyl, octyl, nonyl, and decyl groups; cycloalkyl groups such as cyclopentyl, cyclohexyl, and cycloheptyl groups; and groups in which some or all of the hydrogen atoms in these hydrocarbon groups are substituted with halogen atoms, cyano groups, etc. (for example, halogen-substituted alkyl groups or cyano-substituted alkyl groups such as chloromethyl, 2-bromoethyl, 3,3,3-trifluoropropyl, 3-chloropropyl, and cyanoethyl groups). 2 The number of carbon atoms is, for example, 1 to 10, preferably 1 to 8. 2 The group is preferably a methyl group, an ethyl group, a propyl group, a phenyl group, or a 3,3,3-trifluoropropyl group, and is particularly preferably a methyl group.

[0035] (B) Specifically, examples of component (B) include tris(dimethylhydrogensiloxy)phenylsilane, dimethylsiloxane-diphenylsiloxane copolymer with dimethylhydrogensiloxy groups sealed at both ends of the molecular chain, dimethylsiloxane-diphenylsiloxane-methylhydrogensiloxane copolymer with trimethylsiloxy groups sealed at both ends of the molecular chain, and mixtures of two or more organopolysiloxanes thereof.

[0036] These organopolysiloxanes may be commercially available or manufactured by methods known to those skilled in the art.

[0037] The viscosity of component (B) at 25°C is not particularly limited. The viscosity of component (B) at 25°C is, for example, 5 mPa·s or more and 10,000 mPa·s or less, preferably 10 mPa·s or more and 5,000 mPa·s or less, and more preferably 20 mPa·s or more and 1,000 mPa·s or less. When multiple organopolysiloxanes are used in combination as component (B), the viscosity mentioned above is the value measured using the entire combined component (B).

[0038] When the total amount of components (A), (B), and (C) is 100 parts by mass, the content of component (B), which is organopolysiloxane, is 3 parts by mass or more and 15 parts by mass or less, and may be 4 parts by mass or more and 12 parts by mass or less, 5 parts by mass or more and 10 parts by mass or less, or 6 parts by mass or more and 9 parts by mass or less. By having an appropriate content of component (B), which is organopolysiloxane, the hardness of the heat-conductive silicone adhesive composition after curing will be within an appropriate range. Furthermore, by having an appropriate content of component (B), which is organopolysiloxane, the compatibility with component (C), which will be described later, will be improved, component (C) will bond more easily with component (B), and consequently the adhesiveness of the heat-conductive silicone adhesive composition will be further improved.

[0039] ((C) component) Component (C) is a non-silicone organic compound having at least one alkenyl group and at least one aromatic ring in one molecule. Here, "non-silicone organic compound" refers to a compound having repeating siloxane bond units (-[SiR2-O]) in its molecule. n- (where R is any group and n≧2) refers to an organic compound that does not contain Component (C). Component (C) is a component that contributes to the adhesion of the thermally conductive silicone adhesive composition. In particular, because Component (C) has an aromatic ring, the thermally conductive silicone adhesive composition has sufficient adhesion even to polycarbonate, which is known to be a poorly bonded resin. The reason for this is not entirely clear, but in addition to hydrophobic interactions (compatibility), π-π interactions may also be influencing this when the resin to be bonded has an aromatic ring (e.g., polycarbonate, semi-aromatic polyester, fully aromatic polyester, semi-aromatic polyamide, and fully aromatic polyamide, etc.).

[0040] The molecular weight of component (C) is not particularly limited. The molecular weight of component (C) may be, for example, in the range of 90 to 1,000, preferably in the range of 100 to 800, more preferably in the range of 200 to 500, and even more preferably in the range of 250 to 400.

[0041] The alkenyl group of component (C) is not particularly limited, but from the viewpoint of reactivity, a group having a carbon-carbon double bond at its terminus is preferred. The number of carbon atoms in the alkenyl group is not particularly limited, but it is preferably 2 to 20, more preferably 2 to 10, and even more preferably 2 to 5. Examples of such alkenyl groups include, but are not limited to, vinyl, allyl, 3-butenyl, 4-pentenyl, 5-hexenyl, 6-heptenyl, 7-octenyl, 2-methylpropa-2-en-1-yl, 3-methylbuta-3-en-1-yl, and 2,2-dimethylpropa-2-en-1-yl. Among these, vinyl or allyl groups are preferred.

[0042] The number of alkenyl groups in one molecule of component (C) is not particularly limited. The number of alkenyl groups in one molecule of component (C) may be, for example, 1 to 10, preferably 1 to 5, and more preferably 2 to 4.

[0043] The aromatic ring of component (C) is not particularly limited. Examples of aromatic rings include, but are not limited to, benzene rings, naphthalene rings, anthracene rings, furan rings, pyrrole rings, imidazole rings, pyrazole rings, triazole rings, triazole rings, thiophene rings, and thiazole rings. Among these, from the viewpoint of availability, it is preferable that component (C) is a compound having a benzene ring.

[0044] The number of aromatic rings in one molecule of component (C) is not particularly limited. The number of aromatic rings in one molecule of component (C) may be, for example, 1 to 5, preferably 1 to 4, and more preferably 1 to 3. The number of aromatic rings in one molecule of component (C) may be 2.

[0045] The non-silicone organic compound that is component (C) may be, for example, one represented by the following general formula (3).

[0046] [ka]

[0047] In general formula (3), R 3 ~R 8 Each of these independently consists of a hydrogen atom, a halogen atom, an alkyl group with 1 to 20 carbon atoms, an alkenyl group with 2 to 20 carbon atoms, and -OR 9 , and -OSiR 9 A group selected from the group consisting of 3, where R 9 Each of these is independently selected from the group consisting of a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, and an alkenyl group having 2 to 20 carbon atoms. However, R 3 ~R 8 At least one of them is an alkenyl group having 2 to 20 carbon atoms, or R 9 -OR having an alkenyl group with 2 to 20 carbon atoms 9 Or -OSiR 93. Here, preferred alkenyl groups are groups having a carbon-carbon double bond at their terminus, and among these, groups selected from the group consisting of vinyl group, allyl group, 3-butenyl group, 4-pentenyl group, 5-hexenyl group, 6-heptenyl group, 7-octenyl group, 2-methylpropa-2-en-1-yl group, 3-methylbuta-3-en-1-yl group, and 2,2-dimethylpropa-2-en-1-yl group are preferred, with vinyl group or allyl group being more preferred.

[0048] The non-silicone organic compound that is component (C) may be, for example, one represented by the following general formula (4).

[0049] [ka]

[0050] In general formula (4), R 11 ~R 20 Each of these independently consists of a hydrogen atom, a halogen atom, an alkyl group with 1 to 20 carbon atoms, an alkenyl group with 2 to 20 carbon atoms, and -OR 21 , and -OSiR 21 A group selected from the group consisting of 3, where R 21 Each of these is independently selected from the group consisting of a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, and an alkenyl group having 2 to 20 carbon atoms. However, R 11 ~R 20 At least one of them, preferably at least two, is an alkenyl group having 2 to 20 carbon atoms, or R 21 -OR having an alkenyl group with 2 to 20 carbon atoms 21 Or -OSiR 213. Here, preferred alkenyl groups are groups having a carbon-carbon double bond at their terminus, and among these, groups selected from the group consisting of vinyl group, allyl group, 3-butenyl group, 4-pentenyl group, 5-hexenyl group, 6-heptenyl group, 7-octenyl group, 2-methylpropa-2-en-1-yl group, 3-methylbuta-3-en-1-yl group, and 2,2-dimethylpropa-2-en-1-yl group are preferred, with vinyl group or allyl group being more preferred. X is a single bond; a divalent saturated or unsaturated hydrocarbon group having 1 to 20 carbon atoms, preferably 1 to 10 carbon atoms, more preferably 1 to 6 carbon atoms (however, the hydrocarbon group may be substituted with a halogen atom or a hydroxyl group, and a structure selected from the group consisting of -O-, -S-, -C(O)-, -S(O)-, and -S(O)2- may be inserted); a structure selected from the group consisting of -O-;-S-;-C(O)-;-S(O)-; and -S(O)2-.

[0051] Specific examples of non-silicone organic compounds that constitute component (C) include the following compounds:

[0052] [ka]

[0053] [ka]

[0054] [ka]

[0055] [ka]

[0056] These non-silicone organic compounds may be commercially available or manufactured by methods known to those skilled in the art.

[0057] When the total amount of components (A), (B), and (C) is 100 parts by mass, the content of the non-silicone organic compound, which is component (C), is 1 part by mass or more and 25 parts by mass or less, and may be 3 parts by mass or more and 20 parts by mass or less, 5 parts by mass or more and 15 parts by mass or less, or 8 parts by mass or more and 12 parts by mass or less. The adhesion of the thermally conductive silicone adhesive composition is improved by having the content of the non-silicone organic compound, which is component (C), within an appropriate range.

[0058] ((D) component) Component (D) is an addition reaction catalyst. Component (D) promotes the addition reaction (hydrosilylation reaction) between the hydrosilyl group of component (B) and the alkenyl groups of components (A) and (C). Component (D) may be a catalyst known to those skilled in the art.

[0059] Component (D) may include, for example, platinum group metals such as platinum, rhodium, palladium, osmium, iridium, and ruthenium, or these metals immobilized on a fine particle carrier material (e.g., activated carbon, aluminum oxide, silicon oxide). Furthermore, platinum compounds such as platinum halides, platinum-olefin complexes, platinum-alcohol complexes, platinum-alkoxide complexes, platinum-vinylsiloxane complexes, dicyclopentadiene-platinum dichloride, cyclooctadiene-platinum dichloride, and cyclopentadiene-platinum dichloride may also be used as component (D).

[0060] From an economic standpoint, a metal compound catalyst different from the platinum group metal catalysts mentioned above may be used as component (D). For example, a hydrosilylated iron catalyst selected from the group consisting of iron-carbonyl complex catalysts, iron catalysts having a cyclopentadienyl group as a ligand, iron catalysts having a terpyridine ligand, iron catalysts having a terpyridine ligand and a bistrimethylsilylmethyl group, iron catalysts having a bisiminopyridine ligand, iron catalysts having a bisiminoquinoline ligand, iron catalysts having an aryl group as a ligand, iron catalysts having a cyclic or acyclic olefin group having an unsaturated group, and iron catalysts having a cyclic or acyclic olefinyl group having an unsaturated group may be used. In addition, as a hydrosilylation catalyst, a catalyst selected from the group consisting of cobalt catalysts, vanadium catalysts, ruthenium catalysts, iridium catalysts, samarium catalysts, nickel catalysts, and manganese catalysts may be used.

[0061] The amount of component (D) should be an effective amount corresponding to the desired curing temperature and curing time depending on the application. The amount of component (D) is preferably in the range of 20 ppm to 60,000 ppm, more preferably 200 ppm to 40,000 ppm, and even more preferably 2,000 ppm to 20,000 ppm, relative to the total amount of components (A), (B), and (C), as a concentration of the catalyst metal element. By setting the amount of component (D) within an appropriate range, the addition reaction can be carried out efficiently while suppressing costs.

[0062] ((E) component) Component (E) is a thermally conductive filler. Component (E) contributes to the thermal conductivity (heat dissipation) of the thermally conductive silicone adhesive composition. Component (E) may be at least one selected from the group consisting of metals, metal oxides, metal hydroxides, metal nitrides, and metal carbides. The thermally conductive filler may be an amphoteric oxide or an amphoteric hydroxide. The thermally conductive filler may be used alone or in combination of two or more types. If electrical insulation is required for the cured product, a non-conductive thermally conductive filler may be used.

[0063] As a thermally conductive filler, it is preferable to use at least one selected from the group consisting of aluminum oxide, aluminum hydroxide, magnesium oxide, magnesium hydroxide, zinc oxide, aluminum nitride, and boron nitride, and it is more preferable to include at least one selected from the group consisting of aluminum hydroxide and aluminum oxide. Aluminum oxide is suitable as a thermally conductive filler because it is an insulating material, has relatively good compatibility with other components, is available in a wide range of particle sizes industrially, is readily available as a resource, and is relatively inexpensive. When spherical aluminum oxide is used as a thermally conductive filler, α-alumina obtained by high-temperature thermal spraying or hydrothermal treatment of alumina hydrate may be used. The thermally conductive filler may have OH groups on its surface.

[0064] The shape, particle size, and specific surface area of ​​the thermal conductive filler, which is component (E), can be appropriately selected according to the properties required for the thermal conductive silicone adhesive composition. The shape of the thermal conductive filler may be, for example, spherical, amorphous, powdery, fibrous, plate-like, or flaky. In order to incorporate the amount of thermal conductive filler necessary to increase the thermal conductivity of the cured product, the shape of the thermal conductive filler is preferably spherical. Here, "spherical" does not only mean perfectly spherical, but also any shape that has a rounded shape. Multiple thermal conductive fillers with different shapes may be used in combination as component (E). Using multiple thermal conductive fillers with different shapes makes it easier to fill them in a state close to close packing, resulting in a higher thermal conductivity. When spherical thermal conductive fillers and non-spherical thermal conductive fillers are used in combination, if the proportion of spherical thermal conductive fillers is 30% by mass or more when the total amount of component (E) is 100% by mass, it is possible to further increase the thermal conductivity. The average particle size of the thermally conductive filler may be 0.01 μm or more and 100 μm or less, preferably 0.1 μm or more and 80 μm or less, and more preferably 0.5 μm or more and 70 μm or less. If the average particle size is sufficiently large, the fluidity of the silicone composition is further improved. If the average particle size is sufficiently small, a decrease in dispensability and the jamming of the filler in the sliding parts of the coating device are suppressed. The average particle size of component (E) is D50 (median diameter), which is the 50% particle size in the volume-based cumulative particle size distribution measured by a laser diffraction particle size analyzer.

[0065] The thermally conductive filler, which is component (E), preferably has a thermal conductivity of 10 W / m·K or higher. By using a thermally conductive filler with an appropriate thermal conductivity, the thermal conductivity of the thermally conductive silicone adhesive composition is sufficiently ensured.

[0066] Component (E) should be included in an amount necessary to increase the thermal conductivity of the cured product (for example, 0.5 W / m·K or higher). When the total amount of components (A), (B), and (C) is 100 parts by mass, the content of component (E) is preferably 40 parts by mass or more and 300 parts by mass or less, preferably 50 parts by mass or more and 250 parts by mass or less, more preferably 60 parts by mass or more and 200 parts by mass or less, and even more preferably 70 parts by mass or more and 150 parts by mass or less. By having a suitable content of component (E), the thermally conductive silicone adhesive composition is given sufficient thermal conductivity, and the balance of adhesion, viscosity before curing, ease of mixing, hardness after curing, and specific gravity is appropriate.

[0067] The thermally conductive silicone adhesive composition according to this embodiment may further contain fillers that do not fall under component (E). Such fillers are selected from, for example, fumed silica, crystalline silica, precipitated silica, hollow fillers, silsesquioxane, magnesium carbonate, calcium carbonate, zinc carbonate, layered mica, carbon black, diatomaceous earth, glass fiber, silicone rubber powder, silicone resin powder, etc., and do not fall under component (E). From the viewpoint of viscosity, adhesion, and heat dissipation before curing of the thermally conductive silicone adhesive composition, the thermally conductive silicone adhesive composition according to this embodiment has a BET specific surface area of ​​500 m². 2 The filler content, which is 1 / g or more, is preferably 5% by mass or less, more preferably 3% by mass or less, and even more preferably 1% by mass or less, when the total thermally conductive silicone adhesive composition is considered to be 100% by mass. In this specification, the BET specific surface area is the value obtained by measuring the amount of gas physically adsorbed on the particle surface when the particles are in a low-temperature state and calculating the specific surface area.

[0068] (Component F) The thermally conductive silicone adhesive composition according to this embodiment may further contain, as component (F), a cyclic organopolysiloxane having at least one hydrosilyl group in one molecule. When the thermally conductive silicone adhesive composition contains component (F), the adhesion and hardness after curing tend to improve. Component (F) may contain 4 to 8 silicon atoms.

[0069] The (F) component may be, for example, the one represented by the following general formula (5).

[0070] [ka]

[0071] In general formula (5), m is an integer between 4 and 8, and R a It is a monovalent hydrocarbon group having 1 to 6 carbon atoms.

[0072] By using the cyclic organopolysiloxane represented by general formula (5), the crosslinking density can be improved even with small amounts, and at the same time, sufficient pot life can be ensured due to the steric hindrance caused by the cyclic structure.

[0073] As for component (F), only one of the following types may be used in general formula (5) where m=4, 5, 6, 7, or 8, or two or more different types may be used in combination. For example, three types, one with m=5, one with m=6, and one with m=7, may be used in combination, or four types, one with m=4, one with m=5, one with m=6, and one with m=7, may be used in combination. When using two or more different (F) components, it is preferable to increase the amounts of the m=5 and m=6 components. For example, if the total amount of (F) components contained in the thermally conductive silicone adhesive composition is 100 parts by mass, then the composition may contain m=4 in the proportion of 0 to 10 parts by mass, m=5 in the proportion of 10 to 70 parts by mass, m=6 in the proportion of 10 to 70 parts by mass, m=7 in the proportion of 0 to 30 parts by mass, and m=8 in the proportion of 0 to 10 parts by mass.

[0074] (F) Component is particularly preferably at least one selected from the group consisting of 1,3,5,7,9-pentamethylcyclopentasiloxane (HD5) and 1,3,5,7,9,11-hexamethylcyclohexasiloxane (HD6).

[0075] When the total amount of components (A), (B), and (C) is 100 parts by mass, the content of component (F) may be 0 parts by mass or more and 2 parts by mass or less, 0.2 parts by mass or more and 1 part by mass or less, or 0.4 parts by mass or more and 0.6 parts by mass or less. Including component (F) in an appropriate amount tends to improve the adhesion and hardness of the thermally conductive silicone adhesive composition.

[0076] ((G) component) The thermally conductive silicone adhesive composition according to this embodiment may further contain a condensation reaction catalyst as component (G). When the thermally conductive silicone adhesive composition contains component (G), the adhesion of the cured product at room temperature is further improved. Typically, condensation groups such as hydroxyl groups, carboxyl groups, alkoxy groups, alcohol groups, keto groups, ester groups, acrylic groups, ether groups, and phenol groups are present on the surface of metal substrates such as aluminum and organic resin substrates such as polycarbonate. Component (G) promotes condensation between such condensation groups and alkoxy groups, hydroxyl groups, or hydrosilyl groups present in the thermally conductive silicone adhesive composition.

[0077] Component (G) can be a compound of a metal selected from magnesium, aluminum, titanium, chromium, iron, cobalt, nickel, copper, zinc, zirconium, tungsten, and bismuth. Specifically, organic acid salts, alkoxides, and chelate compounds of aluminum(III), titanium(IV), iron(III), cobalt(III), zinc(II), zirconium(IV), and bismuth(III) may be used. In these metal compounds, the ligands may be organic acids such as octic acid, lauric acid, and stearic acid; alkoxides such as propoxide and butoxide; and polydentate ligands such as catechol, crown ether, polycarboxylic acid, hydroxy acid, and ethyl acetacetate. Compounds in which multiple types of ligands are bonded to a single metal can also be used. Metal chelate compounds containing alkoxy groups are particularly preferred. Compounds of titanium, zirconium, and aluminum are particularly preferred because they easily provide stable curability even if the formulation and usage conditions differ somewhat. (G) For example, titanium diisopropoxybis(ethyl acetoacetate) may be used as component (G).

[0078] The amount of component (G) can be appropriately set depending on the composition of the thermally conductive silicone adhesive composition and the curing conditions. The concentration of the catalyst metal element in component (G) is preferably in the range of 100 ppm to 100,000 ppm, more preferably 1,000 ppm to 50,000 ppm, and even more preferably 5,000 ppm to 30,000 ppm, per 100 parts by mass of the total amount of components (A), (B), and (C).

[0079] (Other ingredients) (Low molecular weight cyclic siloxane) The thermally conductive silicone adhesive composition according to this embodiment may contain one or more selected from the group consisting of octamethylcyclotetrasiloxane (D4), decamethylcyclopentasiloxane (D5), dodecamethylcyclohexasiloxane (D6), tetradecamethylcycloheptasiloxane (D7), and hexadecamethylcyclooctasiloxane (D8). The total content of D4, D5, D6, D7, and D8 may be less than 0.3 parts by mass (less than 3,000 ppm) or less than 0.1 parts by mass (less than 1,000 ppm) when the total amount of components (A), (B), and (C) is 100 parts by mass. It is preferable that the thermally conductive silicone adhesive composition according to this embodiment substantially does not contain D4 to D8. If the total content of D4 to D8 in the thermally conductive silicone adhesive composition is within the above range, the flash point of the composition as a whole will be increased, and safety during storage will be improved. Furthermore, by curing the composition, it becomes possible to provide a cured product that is less likely to cause contact problems with electronic components and the like.

[0080] A thermally conductive silicone composition in which the total content of D4 to D8 is less than 0.3 parts by mass when the total amount of components (A), (B), and (C) is 100 parts by mass can be produced by using component (A) in which the total content xA of D4 to D8 is less than 0.3 parts by mass, component (B) in which the total content xB of D4 to D8 is less than 0.3 parts by mass, and component (C) in which the total content xC of D4 to D8 is less than 0.3 parts by mass, such that xA + xB + xC < 0.3 parts by mass. As a method for reducing the content of D4 to D8 in each component, heating and vacuum treatment is widely known, and for example, it is desirable to perform heating and vacuum treatment at 180°C and 20 mmHg for about 8 hours when preparing the raw materials for each component. The content of D4 to D8 can be measured by conventionally known methods using gas chromatography.

[0081] (Low molecular weight linear siloxane) The thermally conductive silicone adhesive composition according to this embodiment may contain one or more selected from the group consisting of octamethyltrisiloxane (L3), decamethyltetrasiloxane (L4), and dodecamethylpentasiloxane (L5). The total content of L3, L4, and L5 may be less than 0.3 parts by mass (less than 3,000 ppm) or less than 0.1 parts by mass (less than 1,000 ppm) when the total amount of components (A), (B), and (C) is 100 parts by mass. It is preferable that the thermally conductive silicone adhesive composition according to this embodiment substantially does not contain L3 to L5. If the total content of L3 to L5 in the thermally conductive silicone adhesive composition is within the above range, changes in material properties due to the volatilization of L3 to L5 can be suppressed.

[0082] A thermally conductive silicone composition in which the total content of L3 to L5 is less than 0.3 parts by mass when the total amount of components (A), (B), and (C) is 100 parts by mass can be produced by using component (A) in which the total content yA of L3 to L5 is less than 0.3 parts by mass, component (B) in which the total content yB of L3 to L5 is less than 0.3 parts by mass, and component (C) in which the total content yC of L3 to L5 is less than 0.3 parts by mass, such that yA + yB + yC < 0.3 parts by mass. As a method for reducing the content of L3 to L5 in each component, heating and vacuum treatment is widely known, and for example, it is desirable to perform heating and vacuum treatment at 180°C and 20 mmHg for about 8 hours when preparing the raw materials for each component. The content of L3 to L5 can be measured by conventionally known methods using gas chromatography.

[0083] The thermally conductive silicone adhesive composition according to this embodiment may further contain, to the extent that it does not impair the objective of the present invention, optional components other than those described above, which are conventionally known additives to silicone compositions. Examples of such additives include crosslinking agents, silane coupling agents, adhesion aids, pigments, dyes, curing inhibitors (reaction retarders), heat-resistant agents, flame retardants, antistatic agents, conductivity-imparting agents, airtightness-enhancing agents, radiation shielding agents, electromagnetic shielding agents, preservatives, stabilizers, organic solvents, plasticizers, fungicides, and organopolysiloxanes not included in any of the above. The thermally conductive silicone adhesive composition may contain one of these further optional components alone, or it may contain two or more of them.

[0084] (Crosslinking agent) The thermally conductive silicone adhesive composition of the present invention may contain a crosslinking agent different from components (B) and (F). As the crosslinking agent, for example, an organohydrogenpolysiloxane not belonging to the definitions of components (B) and (F) can be used. The crosslinking agent forms a cured product by an addition reaction with alkenyl groups and may have at least one hydrosilyl group in the side chain of the molecule. Preferably, the crosslinking agent has three or more hydrosilyl groups in one molecule and at least one hydrosilyl group in the side chain of the molecule. As the crosslinking agent, an organohydrogenpolysiloxane having five or more hydrosilyl groups may be used, or an organohydrogenpolysiloxane having 10 to 15 hydrosilyl groups may be used. The organohydrogenpolysiloxane that is the crosslinking agent may have at least two hydrosilyl groups in its side chain. The number of hydrosilyl groups at the end of the molecular chain may be zero to two, but two is economically preferable. The molecular structure of organohydrogenpolysiloxane may be linear, branched, or a three-dimensional network structure. There are no particular restrictions on the position of the silicon atom to which the hydrogen atom is bonded; it may be at the end of the molecular chain, at a non-terminant, or on a side chain. Other conditions, such as organic groups other than hydrosilyl groups, bond positions, degree of polymerization, and structure, are not particularly limited, and two or more organohydrogenpolysiloxanes may be used in combination.

[0085] The crosslinking agent is not necessarily required to be included, but if it is included, the amount may be 0 to 10 parts by mass, 1 to 6 parts by mass, or 1 to 4 parts by mass, when the total amount of components (A), (B), and (C) is 100 parts by mass.

[0086] (Silane coupling agent) Examples of silane coupling agents include organosilicon compounds or organosiloxanes having an organic group such as an epoxy group, alkyl group, aryl group, vinyl group, styryl group, methacrylic group, acrylic group, amino group, isocyanurate group, ureido group, mercapto group, isocyanate group, or acid anhydride, and a silicon atom-bonded alkoxy group in one molecule. Examples of silane coupling agents include silane compounds such as octyltrimethoxysilane, octyltriethoxysilane, decyltrimethoxysilane, decyltriethoxysilane, dodecyltrimethoxysilane, dodecyltriethoxysilane, vinyltrimethoxysilane, 3-glycidoxypropyltrimethoxysilane, p-styryltrimethoxysilane, 3-methacryloxypropyltrimethoxysilane, 3-acryloxypropyltrimethoxysilane, 3-aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, tris-(trimethoxysilylpropyl)isocyanurate, 3-ureidopropyltrialkoxysilane, 3-mercaptopropylmethyldimethoxysilane, 3-isocyanatetopropyltriethoxysilane, and 3-trimethoxysilylpropyl succinic anhydride. The silane compounds may be compounds that do not have a hydrosilyl group, and can be used individually or in combination of two or more. By treating the surface of the thermally conductive filler with the silane coupling agent, the affinity with the silicone polymer is improved, the viscosity of the composition can be reduced, and the packing ability of the thermally conductive filler can be improved. Therefore, it becomes possible to incorporate more thermally conductive filler and improve the thermal conductivity.

[0087] The amount of silane coupling agent mixed with the thermally conductive filler should be determined according to the desired curing temperature and curing time for the application. Typically, the silane coupling agent can be used in an amount of 0.5% to 2% by mass relative to the thermally conductive filler. The required amount can be calculated using the following formula, and 1 to 3 times this amount may be added as needed. Required amount of silane coupling agent (g) = Mass of thermally conductive filler (g) × Specific surface area of ​​thermally conductive filler (m²) 2( / g)÷Intrinsic minimum coverage area of ​​silane coupling agent (m²) 2 / g)

[0088] (Adhesive enhancer) As adhesive aids, organosilicon compounds or organosiloxanes having organic functional groups within their molecules, or those containing silyl groups with alkoxy groups bonded to silicon atoms may be used. Preferably, the organic functional group is a silicon atom-bonded alkoxy group. Examples of silicon atom-bonded alkoxy groups include methoxy groups, ethoxy groups, and propoxy groups. Preferred silyl groups containing alkoxy groups bonded to silicon atoms include alkyldialkoxysilyl groups such as methyldimethoxysilyl, ethyldimethoxysilyl, methyldiethoxysilyl, and ethyldiethoxysilyl. These groups may be bonded to silicon atoms via other groups such as alkylene groups. Other organic groups that may be included include alkenyl groups such as vinyl groups, (meth)acrylic groups, hydrosilyl groups, isocyanate groups, epoxy groups, alkyl groups, and aryl groups. In this specification, "(meth)acrylic" is interpreted to include "acrylic," "methacrylic," and both, unless otherwise specified. Preferably, organosilicon compounds or organosiloxanes having at least one organic group (e.g., an epoxy group, an alkyl group, an aryl group, etc.) and at least two or more silicon atom-bonded alkoxy groups are preferred.

[0089] If epoxy groups are included as other organic groups, they may be linear or branched alkyl groups having 1 to 20 carbon atoms, or epoxy groups having aromatic rings. There may be 2 to 3 epoxy groups in one molecule. Examples of epoxy group-containing groups include glycidoxyalkyl groups such as glycidoxypropyl groups; and epoxy-containing cyclohexylalkyl groups such as 2,3-epoxycyclohexylethyl groups and 3,4-epoxycyclohexylethyl groups.

[0090] Specific examples of adhesive aids include tetraethoxysilane, 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropyltriethoxysilane, oligomers of 3-glycidoxypropyltrimethoxysilane, oligomers of 3-glycidoxypropyltriethoxysilane, methacryloxysilanes such as 3-methacryloxypropyltrimethoxysilane and 3-methacryloxypropyltriethoxysilane, 3-trimethoxysilylpropyl succinic anhydride, and frangions such as dihydro-3-(3-(triethoxysilyl)propyl)-2,5-frangion.

[0091] The amount of adhesive aid added should be determined according to the desired curing temperature and curing time for the application, as well as the ratio of the constituent components of the present invention.

[0092] (Pigment) Examples of pigments include titanium dioxide, aluminasilic acid, iron oxide, zinc oxide, calcium carbonate, carbon black, rare earth oxides, chromium oxide, cobalt pigments, ultramarine, cerium silanolate, aluminum oxide, aluminum hydroxide, titanium yellow, barium sulfate, precipitated barium sulfate, and mixtures thereof.

[0093] The amount of pigment added should be determined according to the desired curing temperature and curing time for the application. When pigment is used, the amount added is usually within the range of 0.001% to 5% by mass, preferably 0.01% to 2% by mass, and more preferably 0.05% to 1% by mass, relative to the total mass of the thermally conductive silicone adhesive composition. By setting the amount of pigment within an appropriate range, sufficient coloring can be achieved while suppressing costs, and for example, the first and second liquids described later can be easily distinguished visually.

[0094] (Curing inhibitor (reaction retarder)) Curing inhibitors are compounds that have the ability to adjust the curing rate of addition reactions, and examples include acetylene compounds, hydrazines, triazoles, phosphines, and mercaptans. Any compound known to have a curing inhibitory effect in the art can be used as a curing inhibitor. Examples of such compounds include phosphorus-containing compounds such as triphenylphosphine; nitrogen-containing compounds such as tributylamine, tetramethylethylenediamine, and benzotriazole; sulfur-containing compounds; acetylene compounds; compounds containing two or more alkenyl groups; hydroperoxy compounds; and maleic acid derivatives. Silane or silicone compounds having an amino group may also be used.

[0095] The amount of curing inhibitor to be added should be determined according to the desired curing temperature and curing time for the application, as well as the ratio of the constituent components of the present invention. When a curing inhibitor is used, the amount added is usually within the range of 0.1 parts by mass to 10 parts by mass, preferably 0.2 parts by mass to 5 parts by mass, and more preferably 0.3 parts by mass to 1 part by mass, when the total amount of components (A), (B), and (C) is 100 parts by mass. By adding the curing inhibitor within an appropriate range, it becomes easier to prevent the curing reaction from progressing during the application process, which can worsen workability, and to prevent pump-out due to an excessively slow addition reaction.

[0096] Specific curing inhibitors include various "en-yine" systems such as 3-methyl-3-penten-1-yine and 3,5-dimethyl-3-hexen-1-yine; acetylene alcohols such as 3,5-dimethyl-1-hexyn-3-ol, 1-ethynyl-1-cyclohexanol, and 2-phenyl-3-butyne-2-ol; well-known dialkyl, dialkenyl, and dialkoxyalkyl fumarates and maleates; and those containing cyclovinylsiloxanes.

[0097] (Heat-resistant agent) Examples of heat-resistant additives include cerium hydroxide, cerium oxide, iron oxide, fumed titanium dioxide, and mixtures thereof.

[0098] (Airtightness improving agent) Any substance, organic or inorganic, may be used as an airtightness improving agent, as long as it has the effect of reducing the permeability of the cured material. Specific examples of airtightness improving agents include polyurethane, polyvinyl alcohol, polyisobutylene, isobutylene-isoprene copolymer; talc, mica, glass flakes, and boehmite in sheet form; various metal foils; metal oxide powders; and mixtures thereof.

[0099] (Other conditions) In the thermally conductive silicone adhesive composition according to this embodiment, the number of hydrosilyl groups contained in the composition is preferably in the range of 0.7 to 1.7, more preferably in the range of 0.8 to 1.5, and even more preferably in the range of 0.9 to 1.2, per alkenyl group contained in the composition. In the thermally conductive silicone adhesive composition, having an appropriate number of hydrosilyl groups relative to alkenyl groups makes it easier to suppress an excessive decrease in the hardness of the cured product.

[0100] The thermally conductive silicone adhesive composition according to this embodiment preferably cures at 50°C or below, more preferably at 40°C or below, and even more preferably at 30°C or below. A thermally conductive silicone adhesive composition that can cure at such a relatively low temperature can be suitably used for bonding components such as battery cells and electronic components with low heat resistance.

[0101] [Two-part thermally conductive silicone adhesive] The thermally conductive silicone adhesive composition according to one aspect of the present invention may be used as a one-component adhesive by mixing all components, or it may be a two-component adhesive (two-component thermally conductive silicone adhesive). By using a two-component thermally conductive silicone adhesive, storage stability can be further improved, and it becomes easier to create a composition that cures at low temperatures. The thermally conductive silicone adhesive composition according to one aspect of the present invention may also be a multi-component adhesive of three or more components.

[0102] A two-component thermal conductive silicone adhesive according to one aspect of the present invention comprises a first liquid and a second liquid, which are packaged separately from each other. (A) An organopolysiloxane having a viscosity of 500 mPa·s or more and 1,000,000 mPa·s or less at 25°C, and having at least two alkenyl groups in one molecule, (B) An organopolysiloxane having at least two hydrosilyl groups and at least one aromatic group in one molecule, (C) A non-silicone organic compound having at least one alkenyl group and at least one aromatic ring in one molecule, (D) Addition reaction catalyst, (E) comprising a thermally conductive filler, When the total amount of component (A), component (B), and component (C) in the entire two-component thermal conductive silicone adhesive is 100 parts by mass, The content of component (A) is 65 parts by mass or more and 95 parts by mass or less, The content of component (B) is 3 parts by mass or more and 15 parts by mass or less, The content of component (C) is 1 part by mass or more and 25 parts by mass or less, The content of component (E) is 40 parts by mass or more and 300 parts by mass or less. If component (B) is included in the first liquid, component (D) is not included in the first liquid, and if component (B) is included in the second liquid, component (D) is not included in the second liquid.

[0103] For details of each component, refer to the above description of a thermally conductive silicone adhesive composition according to one aspect of the present invention. The content of each component is the sum of the content of the first liquid and the second liquid.

[0104] In one embodiment of the two-component thermal conductive silicone adhesive, if component (B) is included in the first liquid, component (D) is not included in the first liquid, and if component (B) is included in the second liquid, component (D) is not included in the second liquid. In other words, in the two-component thermal conductive silicone adhesive according to this embodiment, components (B) and (D) are packaged in such a way that they do not coexist. Furthermore, if the two-component thermal conductive silicone adhesive according to this embodiment contains the above-mentioned component (F), components (D) and (F) are packaged in such a way that they do not coexist.

[0105] As long as the aforementioned conditions are met, each component may be contained in only one of the first or second liquid, or in both the first and second liquids. For example, one of the first and second liquids may contain components (A), (C), (D), and (E), while the other contains components (A), (B), and (E). The content of each component in the first and second liquids can be set arbitrarily. For example, the content of each component in each liquid may be set so that the volume and viscosity of the first and second liquids used in mixing are approximately the same. To make it easier to distinguish between the first and second liquids, a pigment may be added to either one or both of the first and second liquids.

[0106] A thermally conductive silicone adhesive composition can be manufactured by a method comprising the step of mixing the first and second components of the two-component thermally conductive silicone adhesive according to this embodiment.

[0107] [Manufacturing methods for electrical equipment, electrical components, electronic equipment, electronic components, or power supply devices] A method for manufacturing an electrical device, electrical component, electronic device, electronic component, or power supply device according to one aspect of the present invention comprises the step of interposing the thermally conductive silicone adhesive composition between a first substrate and a second substrate, and fixing the first substrate and the second substrate to each other by curing the thermally conductive silicone adhesive composition, wherein the curing in the step is performed at 50°C or below. An example of a power supply device is a battery used in automobiles, electric vehicles, etc.

[0108] In one embodiment, the first substrate and the second substrate are parts of different components. In one embodiment, the first substrate is the surface of one battery cell, and the second substrate is the surface of another battery cell. In another embodiment, the first substrate is the surface of a battery cell, and the second substrate is the surface of a case in which the battery cell is housed. In yet another embodiment, the first substrate or the second substrate is a protective material for wiring.

[0109] In one embodiment, the first substrate and the second substrate are each independently a metal or a resin. Examples of metals include aluminum, iron, copper, nickel, gold, silver, or alloys thereof. As for the resin, a resin having an aromatic ring is preferred. Examples of such resins include polycarbonate, semi-aromatic polyester, fully aromatic polyester, semi-aromatic polyamide, fully aromatic polyamide, and the like. In one embodiment, the first substrate and the second substrate are each independently selected from the group consisting of polycarbonate, polyethylene terephthalate, iron electrodeposited with epoxy resin, and aluminum.

[0110] Methods for interposing a thermally conductive silicone adhesive composition between a first substrate and a second substrate include, but are not limited to, a method in which the thermally conductive silicone adhesive composition is applied to one surface of the first or second substrate using a dispenser or the like, and the other surface is then bonded together.

[0111] The curing in the above step is more preferably carried out at 40°C or below, and even more preferably at 30°C or below. The curing in the above step may also be carried out at room temperature. By curing at such a low temperature, heat-sensitive components such as battery cells and electronic components with low heat resistance can be properly bonded.

[0112] Although various aspects and embodiments of the present invention have been illustrated above, the present invention is not limited to these aspects and embodiments, but includes all aspects and embodiments included in the concept and claims of the present invention, and those skilled in the art can modify them in various ways within the scope of the present invention. Such modified aspects and embodiments are also included in the present invention.

[0113] The present invention is illustrated as follows: [1] A thermally conductive silicone adhesive composition, (A) An organopolysiloxane having a viscosity of 500 mPa·s or more and 1,000,000 mPa·s or less at 25°C, and having at least two alkenyl groups in one molecule, (B) An organopolysiloxane having at least two hydrosilyl groups and at least one aromatic group in one molecule, (C) A non-silicone organic compound having at least one alkenyl group and at least one aromatic ring in one molecule, (D) Addition reaction catalyst, (E) comprising a thermally conductive filler, When the total amount of component (A), component (B), and component (C) is 100 parts by mass, The content of component (A) is 65 parts by mass or more and 95 parts by mass or less, The content of component (B) is 3 parts by mass or more and 15 parts by mass or less, The content of component (C) is 1 part by mass or more and 25 parts by mass or less, A thermally conductive silicone adhesive composition having a content of component (E) of 40 parts by mass or more and 300 parts by mass or less. [2] The thermal conductive silicone adhesive composition according to [1], wherein the number of hydrosilyl groups contained in the thermal conductive silicone adhesive composition is in the range of 0.7 to 1.7 for each alkenyl group contained in the thermal conductive silicone adhesive composition. [3](F)A thermally conductive silicone adhesive composition according to [1] or [2], further comprising a cyclic organopolysiloxane having at least one hydrosilyl group in one molecule. [4](G) A thermally conductive silicone adhesive composition according to any one of [1] to [3], further comprising a condensation reaction catalyst. [5] A thermally conductive silicone adhesive composition according to any one of [1] to [3] that cures at 50°C or below.

[0114] [6] A two-component thermal conductive silicone adhesive having a first liquid and a second liquid packaged separately from each other, (A) An organopolysiloxane having a viscosity of 500 mPa·s or more and 1,000,000 mPa·s or less at 25°C, and having at least two alkenyl groups in one molecule, (B) An organopolysiloxane having at least two hydrosilyl groups and at least one aromatic group in one molecule, (C) A non-silicone organic compound having at least one alkenyl group and at least one aromatic ring in one molecule, (D) Addition reaction catalyst, (E) comprising a thermally conductive filler, When the total amount of component (A), component (B), and component (C) in the entire two-component thermal conductive silicone adhesive is 100 parts by mass, The content of component (A) is 65 parts by mass or more and 95 parts by mass or less, The content of component (B) is 3 parts by mass or more and 15 parts by mass or less, The content of component (C) is 1 part by mass or more and 25 parts by mass or less, The content of component (E) is 40 parts by mass or more and 300 parts by mass or less. A two-component thermally conductive silicone adhesive, wherein if component (B) is included in the first liquid, component (D) is not included in the first liquid, and if component (B) is included in the second liquid, component (D) is not included in the second liquid. A method for producing a thermally conductive silicone adhesive composition, comprising the step of mixing the first liquid and the second liquid of the two-component thermally conductive silicone adhesive described in [7][6].

[0115] [8] The process involves interposing a thermally conductive silicone adhesive composition between a first substrate and a second substrate, and curing the thermally conductive silicone adhesive composition to fix the first substrate and the second substrate together. The thermally conductive silicone adhesive composition is the thermally conductive silicone adhesive composition according to claim 1 or 2. A method for manufacturing electrical equipment, electrical components, electronic equipment, electronic components, or power supply devices, wherein the curing in the aforementioned step is performed at a temperature of 50°C or lower. [9] The method for manufacturing an electrical device, electrical component, electronic device, electronic component, or power supply device according to [8], wherein the first substrate and the second substrate are each independently selected from the group consisting of iron and aluminum that have been electrodeposited with polycarbonate, polyethylene terephthalate, epoxy resin, etc. [Examples]

[0116] The present invention will be described in more detail below with reference to examples, but the present invention is not limited in any way by these examples.

[0117] [component] The components used in the examples and comparative examples described below are as follows: (Component A) A-1: A linear dimethylpolysiloxane having one alkenyl group at each end (two in total) and a viscosity of 20,000 mPa·s. A-2: A linear dimethylpolysiloxane having one alkenyl group at each end (two in total) and a viscosity of 500,000 mPa·s. A-3: A linear dimethylpolysiloxane having one alkenyl group at each end (two in total) and a viscosity of 1,000 mPa·s. A-4: A linear dimethylpolysiloxane having one alkenyl group at each end (two in total) and a viscosity of 120 mPa·s.

[0118] ((B) component) B-1: An organohydrogenpolysiloxane having 17 hydrosilyl groups and 6 phenyl groups bonded to silicon atoms in one molecule. B-2: An organohydrogenpolysiloxane having 12 hydrosilyl groups in one molecule and 2 phenyl groups bonded to a silicon atom in one molecule. B-3: Organohydrogenpolysiloxane having a hydrosilyl group and no aromatic group bonded to a silicon atom.

[0119] ((C) component) C-1: 2,2'-diallylbisphenol A having the following structure [ka] C-2: Diallyl ether bisphenol A having the following structure [ka]

[0120] ((D) component) D-1: Platinum-divinyltetramethyldisiloxane complex

[0121] ((E) component) E-1: Aluminum hydroxide E-2: Aluminum Oxide E-3: Zinc Oxide

[0122] (Component F) F-1: 1,3,5,7,9-Pentamethylcyclopentasiloxane (HD5) F-2: A mixture of 1,3,5,7,9-pentamethylcyclopentasiloxane (HD5) and 1,3,5,7,9,11-hexamethylcyclohexasiloxane (HD6).

[0123] ((G) component) G-1: Titanium diisopropoxybis(ethylacetoacetate)

[0124] Others: Hardening inhibitor (reaction retarder) (1-ethynyl-1-cyclohexanol), pigments, etc.

[0125] [Preparation of thermally conductive silicone adhesive compositions] In each example and comparative example, the components were mixed to prepare the first and second solutions. The first solution was prepared to contain components (A), (C), (D), and (E), and the second solution was prepared to contain components (A), (B), and (E). The amounts of each component in the first and second solutions were set so that the thermally conductive silicone adhesive composition obtained by mixing them in a 1:1 ratio would have the composition shown in Tables 1 and 2 below. The first and second solutions were thoroughly mixed with a stirrer and degassed with a vacuum pump to obtain the thermally conductive silicone adhesive compositions of each example and comparative example. The adhesive strength, thermal conductivity, viscosity after mixing, amount of low molecular weight cyclic siloxane, and amount of low molecular weight linear siloxane were evaluated for each obtained thermally conductive silicone adhesive composition.

[0126] [Evaluation Method] (Adhesion strength to aluminum (Al)) Two aluminum plate substrates, approximately 60 cm long x 25 cm wide x 2 mm thick, were prepared. A thermally conductive silicone adhesive composition was applied to one substrate to a thickness of 1 mm in an area of ​​approximately 25 mm long x 25 mm wide. The other substrate was then placed on top and cured at 23°C for 48 hours. The adhesive strength was evaluated by measuring the shear tensile strength in accordance with JIS K6850. The shear tensile strength was measured using a Shimadzu Autograph under conditions of 23°C. The two substrates were pulled in the shear direction at a speed of 50 mm / min, and the stress at which the two substrates separated was defined as the adhesive strength. A good result was judged when the adhesive strength measured in this way was 0.5 MPa or higher.

[0127] (Adhesion strength to polycarbonate (PC)) Except for changing the aluminum plate to a polycarbonate plate, the adhesive strength was measured in the same way as with aluminum. A good result was determined when the adhesive strength measured in this way was 0.5 MPa or higher.

[0128] (Thermal conductivity) A thermally conductive silicone adhesive composition was press-molded into a cylindrical shape with a diameter of 30 mm and a height of 6 mm. The molded product was then cured at 23°C for 24 hours to produce a cylindrical cured object. The thermal conductivity of the cured object was measured using the hot disk method in accordance with ISO 22007-2, with a TPS-500 measuring device (manufactured by Kyoto Electronics Manufacturing Co., Ltd.). Specifically, sensors were placed between the two prepared cylindrical cured objects, and the thermal conductivity was measured using the device. A thermal conductivity of 0.5 W / m·K or higher was considered a good result.

[0129] (Viscosity after mixing) The viscosity of thermally conductive silicone adhesive compositions at 25°C was measured according to JIS K7117-2. Specifically, using a Physica MR 301 manufactured by Anton Paar, the uncured composition was placed between 25 mm diameter parallel plates, and the viscosity was measured under conditions of a shear rate of 10 / s and a gap of 0.5 mm. A viscosity measured in this way between 50 Pa·s and 250 Pa·s was considered to be a good result.

[0130] (Evaluation of low molecular weight cyclic siloxane content) A thermally conductive silicone adhesive composition was press-molded into a 100 mm × 100 mm × 6 mm high plate. The molded product was then cured at 23°C for 24 hours to produce a cured product. 0.3 g of this cured product was weighed and placed in 10 mL of acetone solution in a sample vial, which was sealed and extracted over 12 hours. The content of low molecular weight cyclic siloxanes (octamethylcyclotetrasiloxane (D4), decamethylcyclopentasiloxane (D5), dodecamethylcyclohexasiloxane (D6), tetradecamethylcycloheptasiloxane (D7), and hexadecamethylcyclooctasiloxane (D8)) in this extract was measured using a gas chromatograph.

[0131] (Evaluation of low molecular weight linear siloxane content) A thermally conductive silicone adhesive composition was press-molded into a 100mm x 100mm x 6mm high plate. The molded product was then cured at 23°C for 24 hours to produce a cured product. 0.3g of this cured product was weighed and placed in 10mL of acetone solution in a sample vial, which was sealed and extracted over 12 hours. The content of low molecular weight linear siloxanes (octamethyltrisiloxane (L3), decamethyltetrasiloxane (L4), dodecamethylpentasiloxane (L5)) in this extract was measured using a gas chromatograph.

[0132] The composition and evaluation results of the thermally conductive silicone adhesive compositions in each example and comparative example are shown in Tables 1 and 2 below. In the tables, numbers such as "E1" and "E2" represent the example numbers, and numbers such as "C1" and "C2" represent the comparative example numbers. The numerical values ​​for component content are expressed in parts by mass.

[0133] [Table 1]

[0134] [Table 2]

[0135] As shown in Tables 1 and 2, all of the thermally conductive silicone adhesive compositions in Examples 1 to 15 showed good adhesion to aluminum and polycarbonate after curing at room temperature. Polycarbonate is known as a difficult-to-adhere resin, and adhesive compositions that show good adhesion to polycarbonate are considered to also show good adhesion to polyethylene terephthalate and epoxy resins. Furthermore, all of the thermally conductive silicone adhesive compositions in Examples 1 to 15 showed good thermal conductivity and their viscosity after mixing was within an appropriate range. The thermally conductive silicone adhesive composition in Comparative Example 1 did not contain an organohydrogenpolysiloxane with aromatic groups, resulting in lower adhesion to polycarbonate compared to the Examples due to reduced compatibility with component (C). The thermally conductive silicone adhesive composition in Comparative Example 2 did not contain component (C), resulting in lower adhesion to polycarbonate compared to the Examples. The thermally conductive silicone adhesive composition in Comparative Example 3 had a low content of component (C), resulting in lower adhesion to polycarbonate compared to the Examples. The thermally conductive silicone adhesive composition in Comparative Example 4 had an excessive content of component (C), resulting in lower adhesion to aluminum compared to the example. The thermally conductive silicone adhesive composition in Comparative Example 5 had a low content of thermally conductive filler, resulting in lower thermal conductivity compared to the example, and excessively low viscosity after mixing. The thermally conductive silicone adhesive composition in Comparative Example 6 had an excessive content of thermally conductive filler, resulting in lower adhesion to polycarbonate and aluminum compared to the example, and excessively high viscosity after mixing. The thermally conductive silicone adhesive composition in Comparative Example 7 had low viscosity of component (A), resulting in excessively low viscosity after mixing. The thermally conductive silicone adhesive composition in Comparative Example 8 had a low content of component (B), resulting in insufficient hardness and lower adhesion to polycarbonate and aluminum compared to the example. The thermally conductive silicone adhesive composition in Comparative Example 9 had an excessive content of component (B), resulting in insufficient hardness and lower adhesion to polycarbonate and aluminum compared to the example.

[0136] In each example, the total content of octamethylcyclotetrasiloxane (D4), decamethylcyclopentasiloxane (D5), dodecamethylcyclohexasiloxane (D6), tetradecamethylcycloheptasiloxane (D7), and hexadecamethylcyclooctasiloxane (D8) was less than 0.3 parts by mass when the total amount of components (A), (B), and (C) was set to 100 parts by mass. In addition, in each example, the total content of octamethyltrisiloxane (L3), decamethyltetrasiloxane (L4), and dodecamethylpentasiloxane (L5) was less than 0.1 parts by mass when the total amount of components (A), (B), and (C) was set to 100 parts by mass.

[0137] As can be seen from the results above, the thermally conductive silicone adhesive composition according to one aspect of the present invention has sufficient adhesion to metals and resins even without heat curing at high temperatures.

Claims

1. A thermally conductive silicone adhesive composition, (A) An organopolysiloxane having a viscosity of 500 mPa·s or more and 1,000,000 mPa·s or less at 25°C, and having at least two alkenyl groups in one molecule, (B) An organopolysiloxane having at least two hydrosilyl groups and at least one aromatic group in one molecule, (C) A non-silicone organic compound having at least one alkenyl group and at least one aromatic ring in one molecule, (D) Addition reaction catalyst, (E) A thermally conductive filler, When the total amount of component (A), component (B), and component (C) is 100 parts by mass, The content of component (A) is 65 parts by mass or more and 95 parts by mass or less, The content of component (B) is 3 parts by mass or more and 15 parts by mass or less, The content of component (C) is 1 part by mass or more and 25 parts by mass or less, A thermally conductive silicone adhesive composition having a content of component (E) of 40 parts by mass or more and 300 parts by mass or less.

2. The thermal conductive silicone adhesive composition according to claim 1, wherein the number of hydrosilyl groups contained in the thermal conductive silicone adhesive composition is in the range of 0.7 to 1.7 for each alkenyl group contained in the thermal conductive silicone adhesive composition.

3. (F) Cyclic organopolysiloxane having at least one hydrosilyl group in one molecule A thermally conductive silicone adhesive composition according to claim 1 or 2, further comprising the above.

4. (G) Condensation reaction catalyst A thermally conductive silicone adhesive composition according to claim 1 or 2, further comprising the above.

5. A thermally conductive silicone adhesive composition according to claim 1 or 2, which cures at a temperature of 50°C or lower.

6. A two-component thermal conductive silicone adhesive having a first liquid and a second liquid packaged separately from each other, (A) An organopolysiloxane having a viscosity of 500 mPa·s or more and 1,000,000 mPa·s or less at 25°C, and having at least two alkenyl groups in one molecule, (B) An organopolysiloxane having at least two hydrosilyl groups and at least one aromatic group in one molecule, (C) A non-silicone organic compound having at least one alkenyl group and at least one aromatic ring in one molecule, (D) Addition reaction catalyst, (E) A thermally conductive filler, When the total amount of component (A), component (B), and component (C) in the entire two-component thermal conductive silicone adhesive is 100 parts by mass, The content of component (A) is 65 parts by mass or more and 95 parts by mass or less, The content of component (B) is 3 parts by mass or more and 15 parts by mass or less, The content of component (C) is 1 part by mass or more and 25 parts by mass or less, The content of component (E) is 40 parts by mass or more and 300 parts by mass or less. A two-component thermally conductive silicone adhesive, wherein when component (B) is included in the first liquid, component (D) is not included in the first liquid, and when component (B) is included in the second liquid, component (D) is not included in the second liquid.

7. A method for producing a thermally conductive silicone adhesive composition, comprising the step of mixing the first liquid and the second liquid of the two-component thermally conductive silicone adhesive described in claim 6.

8. The process includes a step of interposing a thermally conductive silicone adhesive composition between a first substrate and a second substrate, and fixing the first substrate and the second substrate to each other by curing the thermally conductive silicone adhesive composition. The thermally conductive silicone adhesive composition is the thermally conductive silicone adhesive composition according to claim 1 or 2. A method for manufacturing electrical equipment, electrical components, electronic equipment, electronic components, or power supply devices, wherein the curing in the aforementioned step is performed at a temperature of 50°C or lower.

9. A method for manufacturing an electrical device, electrical component, electronic device, electronic component, or power supply device according to claim 8, wherein the first substrate and the second substrate are each independently selected from the group consisting of polycarbonate, polyethylene terephthalate, epoxy resin, and aluminum.

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