Two-component curable silicone composition containing a diyne-containing amino-modified organopolysiloxane compound and its cured product

Abstract

Provided is a two-component curable silicone composition that can be stored at room temperature and cured by a [2+2+2] cycloaddition reaction under mild conditions. 【Solution】(A) (A-1) An organopolysiloxane having at least one alkynyl group or nitrile group, and / or (A-2) An organopolysiloxane represented by the average compositional formula (R 1 3SiO 1 / 2 ) a (R 1 2SiO 2 / 2 ) b (R 1 SiO 3 / 2 ) c (SiO 4 / 2 ) d (R 1 is a monovalent hydrocarbon group, a is a number of 2 or more, and a + b + c + d is a number of 2 or more) and having a kinematic viscosity of from 1 to 100,000 mm 2 / s, and (B) An organopolysiloxane compound having a substituent represented by the general formula (2), and TIFF2026047779000015.tif2359 (C) A metal compound capable of catalyzing a [2+2+2] cycloaddition reaction. The first liquid contains (A) and (C) and does not contain (B), and the second liquid contains the component (B) and does not contain the component (C). A two-component curable silicone composition.

Description

[Technical Field]

[0001] The present invention relates to a curable silicone composition comprising an amino-modified organopolysiloxane compound characterized by having a diyne in its molecule and being curable, and to a cured product thereof. [Background technology]

[0002] Silicone elastomers are elastic materials based on silicone resin. Because silicone itself has excellent heat resistance and chemical resistance, they are widely used as coatings, sealants, and encapsulants for semiconductor devices.

[0003] Curable silicone compositions are liquid silicone compositions when used, and curing proceeds in response to heat, light, or moisture in the air, allowing them to be formed into silicone elastomers. Specific curing methods include addition reactions using radicals, addition reactions via hydrosilylation, and condensation reactions. Addition reactions via radicals generally use peroxides, often requiring high temperatures for the generation of the initiating species, and may have poor surface curing properties due to curing inhibition by oxygen. Addition reactions via hydrosilylation can be cured at room temperature or by heating, depending on the adjustment of the catalyst and reaction control agent. However, curing failure may occur if curing inhibitors such as sulfur, phosphorus, nitrogen compounds, water, or organometallic salts are mixed in or come into contact with the composition. Furthermore, while condensation reactions can be cured at room temperature using moisture in the air, they involve gas generation during curing, resulting in volume shrinkage, and have poor deep curing properties.

[0004] Many curable silicone compositions are used around electrical and electronic components and semiconductor devices. However, an increasing number of electrical and electronic components are sensitive to heat and cannot be exposed to high temperatures during mounting. Therefore, there is a need for curable silicone compositions that can be cured under mild conditions of 100°C or below.

[0005] One reaction that can be used as a curing system is the [2+2+2] cycloaddition reaction of alkynes, which uses a transition metal as a catalyst to form carbon-carbon bonds between multiple bonds. The [2+2+2] cycloaddition reaction forms an aromatic ring from three triple bonds and is a very useful reaction as it does not produce any by-product gases. However, there have been no reported applications of this reaction to organopolysiloxane compounds or their cured products. Furthermore, this reaction has a high activation barrier, and when using a catalyst that is stable at room temperature, high temperatures of 100°C or higher are required to proceed. On the other hand, in order to proceed with the reaction under mild conditions below 100°C, a highly active catalyst is required, but such catalysts require prior preparation or become inactive under normal humidity conditions, making it difficult to use them as compositions or to store them for long periods at room temperature or humidity. (Non-patent documents 1-3) [Prior art documents] [Non-patent literature]

[0006] [Non-Patent Document 1] Reppe, W. et al. Justus Liebigs Ann., 1948, 560, 104. [Non-Patent Document 2] Vollhardt, KPC Angew. Chem. Int. Ed. Engl. 1984, 23, 539. [Non-Patent Document 3] Saito, S.; Yamamoto, Y. Chem. Rev. 2000, 100, 2901 [Overview of the project] [Problems that the invention aims to solve]

[0007] In recent years, there has been an increase in electrical and electronic components that are not preferably heated at temperatures above 100°C, as well as modules including circuit boards on which these components are mounted. Low-temperature curing materials that do not need to be cured at high temperatures during mounting are also required from the perspective of energy conservation. In addition, materials that can be stored at room temperature without the need for special temperature control during storage or transportation are required from the perspectives of reducing environmental impact and the burden of material management for users. However, as an advantage of two-component curing materials, there are no examples of materials that can be stored at room temperature and cured at low temperatures by utilizing the above cycloaddition reaction.

[0008] In view of the above circumstances, an object of the present invention is to provide a curable silicone composition that can be stored at room temperature and can cause a [2+2+2] cycloaddition reaction to proceed under particularly mild conditions, as well as a silicone cured product thereof.

Means for Solving the Problems

[0009] In order to solve the above problems, in the present invention, A two-component curable silicone composition, (A) An organopolysiloxane composed of the following component (A-1) and / or component (A-2), (A-1) An organopolysiloxane having at least one alkynyl group or nitrile group in one molecule, and (A-2) The following average composition formula (1) (R 3 / 2 , , 1 , 4 / 2 , , c , d 3SiO 1 / 2 ) a (R 1 2SiO 2 / 2 ) b (R 1 SiO 3 / 2 ) c (SiO 4 / 2 ) d [[ID=,43]] (1) (In the formula, R 1Each of these is an independently unsubstituted or substituted monovalent hydrocarbon group, where a is a number of 2 or more, and a+b+c+d is a number of 2 or more. However, in the case of a linear organopolysiloxane compound, a=2, b is between 2 and 1,200, and c=d=0. In the case of a branched organopolysiloxane compound, a is a number of 2 or more, b is between 2 and 1,200, and c or d is 1 or more. The kinematic viscosity at 25°C, as shown by [formula], is between 1 and 100,000 mm². 2 / s organopolysiloxane, and (B) Organopolysiloxane compounds having substituents represented by the following general formula (2) in the molecule, [ka] (In the formula, R 2 R is independently a substituted or unsubstituted monovalent hydrocarbon group or hydrogen atom, 3 R is an independently substituted or unsubstituted divalent hydrocarbon group. 4 is a divalent linking group. ) and, (C) Metal compounds capable of catalyzing [2+2+2] cycloaddition reactions The present invention provides a two-component curable silicone composition characterized in that, among the above-mentioned components, the first liquid contains (A) and (C) but does not contain (B), and the second liquid contains component (B) but does not contain component (C).

[0010] Such a curable silicone composition of the present invention can be stored at room temperature and can undergo a [2+2+2] cycloaddition reaction under mild conditions, and a cured silicone product can be obtained by curing the composition.

[0011] Furthermore, the organopolysiloxane compound, which is component (A) or component (B), is easy to synthesize.

[0012] In this case, the two-component curable silicone composition of the present invention contains R in the general formula (2). 3 It is preferable that the group is a methylene group.

[0013] Such a component (B) is R in general formula (2). 3 If the compound is an organopolysiloxane compound in which the group is a methylene group, it is easy to synthesize, and a curable silicone composition with suitable performance can be stably provided.

[0014] Furthermore, in the two-component curable silicone composition of the present invention, R in the general formula (2) 2 It is preferable that it is a hydrogen atom.

[0015] Such a component (B) is R in general formula (2). 2 If the organopolysiloxane compound is one in which hydrogen atoms are present, it is easy to synthesize, and a curable silicone composition with suitable performance can be stably provided.

[0016] Furthermore, in the composition of the present invention, it is preferable that component (B) is an organopolysiloxane compound having an average of two or more substituents represented by the general formula (2) in one molecule.

[0017] Such (B) components have an average of four or more ethynylene groups in one molecule that are linked to each other by nitrogen atoms and contribute to [2+2+2] cycloaddition, allowing the [2+2+2] cycloaddition reaction to proceed more smoothly.

[0018] In the present invention, it is preferable that (D) at least one inorganic or organic filler is contained in an amount of 0.1 to 5,000 parts by mass per 100 parts by mass of the total of components (A) and (B).

[0019] Such component (D) can impart various properties to the curable silicone composition of the present invention, such as thermal conductivity, heat resistance, reinforcing properties, electrical conductivity, and design properties, while also providing a uniform composition that is not too viscous and is easy to handle.

[0020] In this case, it is preferable that component (D) is a filler made of one or more materials selected from the group consisting of metals, metal oxides, metal hydroxides, metal nitrides, metal carbides, allotropes of carbon, resins, dyes, and pigments.

[0021] With such a (D) component, it is possible to obtain a composition with desired properties depending on the material.

[0022] Furthermore, the present invention provides a cured silicone product obtained by curing the above-mentioned curable silicone composition.

[0023] The silicone cured product of the present invention is an elastic material, and since silicone itself has excellent heat resistance and chemical resistance, it is useful as a silicone elastomer used as a coating agent, sealant, and encapsulant for semiconductor devices. [Effects of the Invention]

[0024] According to the present invention, by introducing a specific structure into an organopolysiloxane compound, organopolysiloxane compounds and silane compounds useful for [2+2+2] cycloaddition reactions can be provided. In particular, a silicone composition that can be cured under mild conditions of 100°C or below and can be stored at room temperature can be provided. Due to such curing performance, curing is possible even when using components that are sensitive to heat and cannot be exposed to high temperatures during mounting, making it highly valuable as a material used around electrical and electronic components and semiconductor elements. Furthermore, because it is a material that can be stored at room temperature, there is no need to maintain a low temperature of 0°C or below during storage or transportation of the material, which is preferable from the viewpoint of environmental impact and energy consumption. Moreover, the cured silicone product obtained by curing the composition is an elastic material, and since silicone itself has excellent heat resistance and chemical resistance, it is useful as a silicone elastomer used as a coating agent, sealant, or encapsulant for semiconductor elements. Furthermore, the curable silicone composition of the present invention allows for the easy and efficient production of the above composition. [Modes for carrying out the invention]

[0025] As described above, there has been a need for the development of a curable silicone composition that can be cured under mild conditions below 100°C without the use of a highly active catalyst, does not deactivate under normal humidity conditions, and is easy to use as a composition and to store for long periods at room temperature or humidity.

[0026] As a result of diligent research to solve the above problems, the present inventors discovered that by introducing substituents with a specific structure into organopolysiloxane compounds, a [2+2+2] cycloaddition reaction can proceed under mild conditions, leading to the present invention.

[0027] In other words, the present invention is a two-component curable silicone composition, (A) Organopolysiloxanes comprising the following components (A-1) and / or (A-2), (A-1) Organopolysiloxanes having at least one alkynyl group or nitrile group in one molecule, and (A-2) The average composition formula below (R 1 3SiO 1 / 2 ) a (R 1 2SiO 2 / 2 ) b (R 1 SiO 3 / 2 ) c (SiO 4 / 2 ) d (1) (In the formula, R 1 Each of these is an independently unsubstituted or substituted monovalent hydrocarbon group, where a is a number of 2 or more, and a+b+c+d is a number of 2 or more. However, in the case of a linear organopolysiloxane compound, a=2, b is between 2 and 1,200, and c=d=0. In the case of a branched organopolysiloxane compound, a is a number of 2 or more, b is between 2 and 1,200, and c or d is 1 or more. The kinematic viscosity at 25°C, as shown by [formula], is between 1 and 100,000 mm². 2 / s organopolysiloxane, and (B) Organopolysiloxane compounds having substituents represented by the following general formula (2) in the molecule, [ka] (In the formula, R 2 R is independently a substituted or unsubstituted monovalent hydrocarbon group or hydrogen atom, 3 R is an independently substituted or unsubstituted divalent hydrocarbon group. 4 is a divalent linking group. ) and, (C) Metal compounds capable of catalyzing [2+2+2] cycloaddition reactions This is a two-component curable silicone composition characterized in that, among the above-mentioned components, the first liquid contains (A) and (C) but does not contain (B), and the second liquid contains component (B) but does not contain component (C).

[0028] The present invention will be described in detail below, but the present invention is not limited to these descriptions.

[0029] [(A) component] In the present invention, component (A) may be either component (A-1) or component (A-2) described below, either individually or in combination. When used in combination, the ratio of (A-1) to (A-2) is preferably (A-1):(A-2)=99:1 to 1:99, and more preferably (A-1):(A-2)=90:10 to 10:90.

[0030] [(A-1) component] Component (A-1) is an organopolysiloxane having at least one alkynyl group or nitrile group in one molecule.

[0031] The alkynyl group is preferably a monovalent hydrocarbon group having 2 to 8 carbon atoms, more preferably 2 to 6 carbon atoms, and possessing a carbon-carbon triple bond. Examples include terminal alkynes such as ethynyl and propagyl groups, and internal alkynes having a group other than a hydrogen atom on the carbon atom forming the carbon-carbon triple bond. Terminal alkynes are preferred, and ethynyl groups are particularly preferred. The nitrile group is preferably a monovalent functional group having 2 to 8 carbon atoms, more preferably 2 to 6 carbon atoms, and possessing a carbon-nitrogen triple bond. Examples include cyano groups, cyanomethyl groups, and cyanoethyl groups, with cyano groups being preferred.

[0032] The alkynyl group or nitrile group may be bonded to either a silicon atom at the end of the molecular chain, a silicon atom in the middle of the molecular chain, or both.

[0033] The organic groups other than alkynyl or nitrile groups bonded to the silicon atoms of the organopolysiloxane are unsubstituted or substituted monovalent hydrocarbon groups having 1 to 18 carbon atoms, preferably 1 to 10 carbon atoms, and more preferably 1 to 8 carbon atoms. Examples include alkyl groups such as methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, pentyl, neopentyl, hexyl, cyclohexyl, octyl, nonyl, and decyl groups; aryl groups such as phenyl, tolyl, xylyl, and naphthyl groups; aralkyl groups such as benzyl, phenylethyl, and phenylpropyl groups; or groups in which some or all of the hydrogen atoms of these groups are substituted with halogen atoms such as fluorine, bromine, or chlorine, or cyano groups, for example, chloromethyl, chloropropyl, bromoethyl, trifluoropropyl, and cyanoethyl groups. Methyl and trifluoropropyl groups are particularly preferred.

[0034] The organopolysiloxane has a kinematic viscosity at 25°C, for example, 1 to 20,000,000 mm². 2 / s, preferably 10 to 1,000,000 mm 2 / s, more preferably 60-30,000 mm 2 The kinematic viscosity is 1 mm³ / s.2 If the temperature is 20,000,000 mm² or higher, the physical properties of the curable silicone composition are good, and the temperature is 20,000,000 mm². 2 If the value is less than or equal to / s, the spreadability of the curable silicone composition will be sufficient.

[0035] In this invention, the kinematic viscosity of component (A-1) is the value measured at 25°C using an Ostwald viscometer.

[0036] The organopolysiloxane described above is not particularly limited in its molecular structure as long as it possesses the above properties, and examples include linear structures, branched structures, partially branched structures, or linear structures having a cyclic structure. In particular, it is preferable that the main chain consists of repeating diorganosiloxane units and has a linear structure in which both ends of the molecular chain are sealed with triorganosiloxy groups. The organopolysiloxane having a linear structure may also have a partially branched or cyclic structure.

[0037] The organopolysiloxanes can be used individually or in combination of two or more.

[0038] Although component (A-1) is used in the first solution, it may also be used in the second solution.

[0039] [(A-2) component] (A-2) The component is given by the following average composition formula (1) (R 1 3SiO 1 / 2 ) a (R 1 2SiO 2 / 2 ) b (R 1 SiO 3 / 2 ) c (SiO 4 / 2 ) d (1) (In the formula, R 1Each of these is an independently unsubstituted or substituted monovalent hydrocarbon group, where a is a number of 2 or more, and a+b+c+d is a number of 2 or more. However, in the case of a linear organopolysiloxane compound, a=2, b is between 2 and 1,200, and c=d=0. In the case of a branched organopolysiloxane compound, a is a number of 2 or more, b is between 2 and 1,200, and c or d is 1 or more. The kinematic viscosity at 25°C, as shown by [formula], is between 1 and 100,000 mm². 2 It is an organopolysiloxane compound of / s.

[0040] The organic group bonded to the silicon atom of the organopolysiloxane is an unsubstituted or substituted monovalent hydrocarbon group having 1 to 18 carbon atoms, preferably 1 to 10 carbon atoms, and more preferably 1 to 8 carbon atoms. Examples include alkyl groups such as methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, pentyl, neopentyl, hexyl, cyclohexyl, octyl, nonyl, and decyl groups; aryl groups such as phenyl, tolyl, xylyl, and naphthyl groups; aralkyl groups such as benzyl, phenylethyl, and phenylpropyl groups; or groups in which some or all of the hydrogen atoms of these groups are substituted with halogen atoms such as fluorine, bromine, or chlorine, or cyano groups, for example, chloromethyl, chloropropyl, bromoethyl, trifluoropropyl, and cyanoethyl groups. Methyl, phenyl, and trifluoropropyl groups are particularly preferred.

[0041] The organopolysiloxane has a kinematic viscosity of 1 to 100,000 mm² at 25°C. 2 / s, preferably 10-50,000 mm 2 / s, more preferably 60-30,000 mm 2 The kinematic viscosity is 1 mm³ / s. 2 If the value is 1 / s or higher, the physical properties of the silicone composition are good, and 100,000 mm 2 If the viscosity is less than / s, a material with a viscosity that is easy to handle as a silicone composition can be obtained.

[0042] In this invention, the kinematic viscosity of component (A-2) is the value measured at 25°C using an Ostwald viscometer.

[0043] The organopolysiloxane described above is not particularly limited in its molecular structure as long as it possesses the above properties, and examples include linear structures, branched structures, partially branched structures, or linear structures having a cyclic structure. In particular, it is preferable that the main chain consists of repeating diorganosiloxane units and has a linear structure in which both ends of the molecular chain are sealed with triorganosiloxy groups. The organopolysiloxane having a linear structure may also have a partially branched or cyclic structure.

[0044] The organopolysiloxanes can be used individually or in combination of two or more.

[0045] Although component (A-2) is used in the first solution, it may also be used in the second solution.

[0046] (A) The amount of component included is preferably 1% by mass or more and 99% by mass or less of the total composition, and more preferably 2% by mass or more and 50% by mass or less. If component (D) described below is not included, it is more preferable that it be 10% by mass or more and 90% by mass or less of the total composition, and more preferably 20% by mass or more and 50% by mass or less. If component (D) is included, it is more preferable that it be 1% by mass or more and 80% by mass or less, and more preferably 2% by mass or more and 20% by mass or less.

[0047] [(B) Component] The organopolysiloxane compound that is component (B) of the present invention is an organopolysiloxane compound having substituents represented by the following general formula (2) in its molecule. Such component (B) is a compound containing a diyne having two carbon-carbon triple bonds, and this diyne contributes to [2+2+2] cycloaddition. [ka] (In the formula, R2 R is independently a substituted or unsubstituted monovalent hydrocarbon group or hydrogen atom, 3 R is an independently substituted or unsubstituted divalent hydrocarbon group. 4 (This is a divalent linking group.)

[0048] In equation (2) above, R 2 These are independently substituted or unsubstituted monovalent hydrocarbon groups or hydrogen atoms. Specifically, monovalent hydrocarbon groups include alkyl groups such as methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, pentyl, hexyl, cyclohexyl, octyl, and dodecyl groups; aryl groups such as phenyl, 1-naphthyl, 2-naphthyl, and tolyl groups; aralkyl groups such as benzyl and 2-phenylethyl groups; and chloromethyl and 3,3,3-trifluoropropyl groups, in which some or all of the hydrogen atoms of these groups are substituted with halogen atoms such as fluorine, chlorine, and bromine. However, from the viewpoint of ease of synthesis, methyl, ethyl, phenyl, and hydrogen atoms are preferred, and hydrogen atoms are particularly preferred.

[0049] In equation (2) above, R 3 These are independently substituted or unsubstituted divalent hydrocarbon groups. Specifically, examples of divalent hydrocarbon groups include alkylene groups such as methylene, ethylene, ethylidene, propylene, trimethylene, propylene, propyridene, and isopropylidene. However, from the viewpoint of ease of synthesis, methylene and ethylene groups are preferred, and methylene groups are particularly preferred.

[0050] In equation (2) above, R 4The linking group is a divalent linking group. The divalent linking group is not particularly limited, but examples include linear, branched, or ring-containing aliphatic hydrocarbon groups or aromatic hydrocarbon groups. The aliphatic hydrocarbon group or aromatic hydrocarbon group may have substituents, and examples of substituents include alkyl groups, alkoxy groups, halogen atoms, alkyl halides, hydroxyl groups, and carbonyl groups. In addition, some of the carbon atoms or hydrogen atoms constituting the hydrocarbon group may be replaced by bonds such as ether bonds, ester bonds, carbonyl bonds, carbonate bonds, carbamate bonds, amino bonds, urethane bonds, and urea bonds. Linear aliphatic hydrocarbon groups, aromatic hydrocarbon groups, or hydrocarbon groups having amino bonds are preferred as divalent linking groups, and linear aliphatic hydrocarbon groups are particularly preferred. The number of carbon atoms in the linear aliphatic hydrocarbon group is preferably 1 to 20, more preferably 1 to 10, and particularly preferably 1 to 3.

[0051] Specifically, the substituents mentioned above are: [ka] Examples of structures include the following. In the structural formulas described above, Me represents a methyl group, Et represents an ethyl group, and Ph represents a phenyl group.

[0052] Among the substituents mentioned above, the following structure is particularly preferred from the viewpoint of ease of synthesis and reactivity in the [2+2+2] cycloaddition reaction. [ka]

[0053] The aforementioned component (B) preferably contains one or more substituents shown in formula (2) above in one molecule, and particularly preferably contains an average of two or more substituents. Such a component (B) has at least two, more preferably four or more, ethynylene groups that contribute to the [2+2+2] cycloaddition, and these are linked to each other by nitrogen atoms, making it easy to synthesize and allowing the [2+2+2] cycloaddition reaction to proceed smoothly.

[0054] Furthermore, in the present invention, it is preferable that component (B) is an organopolysiloxane compound having an average of two or more substituents represented by the general formula (2) in one molecule. Here, "having an average of two or more substituents in one molecule" means that if there is only one compound of component (B), it has two or more of the above substituents in that molecule, and if there are two or more compounds, the sum of the number of above substituents in each molecule and the mole fraction of each molecule is 2 or more.

[0055] Furthermore, the molecular structure of component (B) is not particularly limited as long as it is a compound containing the substituent shown in the general formula (2), and examples include a linear structure, a branched structure, a partially branched structure, or a linear structure having a cyclic structure. In particular, it is preferable that the main chain consists of repeating diorganosiloxane units and has a linear structure in which both ends of the molecular chain are sealed with triorganosiloxy groups. The organopolysiloxane having the linear structure may also have a partially branched or cyclic structure. The substituent shown in formula (2) may be present on the triorganosiloxy groups at the ends of the molecular chain, or on the partially branched or cyclic structure.

[0056] The aforementioned component (B) preferably has an average molecular weight of 150 to 500,000 g / mol, and particularly preferably 250 to 150,000 g / mol. Here, the average molecular weight refers to the sum of the products of the molecular weight and mole fraction of each compound, i.e., the number-average molecular weight. The average molecular weight can be measured by GPC (gel permeation chromatography) using tetrahydrofuran as the eluent and polystyrene as the standard substance.

[0057] The kinematic viscosity of component (B) at 25°C is preferably 1 to 100,000 mm². 2 The range is / s, more preferably 5 to 30,000 mm 2 / s, and more preferably 10 to 5,000 mm 2 This kinematic viscosity is 10-5,000 mm². 2When the value is / s, the cured product obtained from the composition will have superior strength, fluidity, and workability. The kinematic viscosity is measured using the Ostwald viscosity at 25°C.

[0058] The aforementioned component (B) preferably has an amine value of 0.1 to 2000 mg KOH / g. The amine value is the number of mg of potassium hydroxide (KOH: 56.11) equivalent to the acid required to neutralize 1 g of the sample.

[0059] Examples of organopolysiloxane compounds of the present invention that satisfy the above requirements include the following general formula (3): (R 5 3SiO 1 / 2 ) e (R 5 2SiO 2 / 2 ) f (R 5 SiO 3 / 2 ) g (SiO 4 / 2 ) h (3) (In the formula, R 5 R is independently an unsubstituted or substituted monovalent hydrocarbon group, however R 5 At least one of the substituents is shown in formula (2) above, and e + f + g + h is a number of 0 or more. However, in the case of a linear organopolysiloxane compound, e = 2, f is preferably between 2 and 1,200, and g = h = 0. In the case of a branched organopolysiloxane compound, e is a number of 0 or more, f is preferably between 2 and 1,200, and g or h is 1 or more. In the case of a cyclic organopolysiloxane compound, e = 0, f is preferably in the range of 3 to 10, more preferably in the range of 3 to 6, and g or h is a number of 0 or more. Examples of organopolysiloxane compounds represented by [formula] include [formula].

[0060] Specifically, the organopolysiloxane and silane compounds mentioned above are: [ka] (In the formula, i, j, or k are numbers greater than or equal to 0, and i or j are more preferably between 2 and 1,200. l or m are numbers greater than or equal to 0, and l+m are more preferably between 20 and 1,200.) Examples of structures include the following. In the structural formulas described above, Me represents a methyl group and Ph represents a phenyl group.

[0061] [2+2+2] cycloaddition reactions using metal catalysts are a direct and atomically efficient method for synthesizing condensed polycyclic aromatic compounds. Component (A) of the present invention is a metal compound capable of catalyzing [2+2+2] cycloaddition reactions, and is particularly characterized by the fact that the reaction proceeds under relatively mild conditions below 100°C.

[0062] The aforementioned component (B) can be used individually or in combination of two or more types.

[0063] The amount of component (B) is preferably 1% by mass or more and 99% by mass or less of the total composition, and more preferably 2% by mass or more and 70% by mass or less. If component (D) is not included, it is more preferably 10% by mass or more and 90% by mass or less of the total composition, and more preferably 30% by mass or more and 70% by mass or less. If component (D) is included, it is more preferably 1% by mass or more and 80% by mass or less, and more preferably 2% by mass or more and 30% by mass or less.

[0064] Note that component (B) is used in the second liquid and is not contained in the first liquid. If component (B) is included in the first liquid, its storage stability will deteriorate, and it will harden while stored at room temperature. Therefore, if component (B) is included, the first liquid cannot be stored at room temperature.

[0065] [(C) component] Component (C) is a metal compound capable of catalyzing the [2+2+2] cycloaddition reaction, and is formulated as a catalyst for curing the curable silicone composition of the present invention. Here, "capable of catalyzing the [2+2+2] cycloaddition reaction" means having catalytic activity for the [2+2+2] cycloaddition reaction. Hereinafter, the metal compound is also simply referred to as "catalyst", "metal catalyst", etc.

[0066] The metal compound of the component (C) can be composed of a central metal atom, a ligand, and a counter ion. Examples of the central metal atom include those from Group 4 to Group 12. Specifically, Group 4 (titanium (Ti), zirconium (Zr), hafnium (Hf)), Group 5 (vanadium (V), niobium (Nb), tantalum (Ta)), Group 6 (chromium (Cr), molybdenum (Mo), tungsten (W)), Group 7 (manganese (Mn), rhenium (Re)), Group 8 (iron (Fe), ruthenium (Ru), osmium (Os)), Group 9 (cobalt (Co), rhodium (Rh), iridium (Ir)), Group 10 (nickel (Ni), palladium (Pd), platinum (Pt)), Group 12 (zinc (Zn)) can be mentioned. Among them, Ti, Nb, Ta, Co, Rh, Fe, Ru, Ir or Pd are preferred, and Co, Rh or Pd are more preferred. The central metal atom may be one kind or two or more kinds. In the case of two or more kinds, they may all be the same metal or a combination of different metals.

[0067] The ligand is not particularly limited, and examples include carbonyl (CO), ammonia, water, F - , Cl - , Br - , I - and other halide ions, cyanide ion (CN - ), PF6 - , BF4 - , NO3 - , BPh4 - , ClO4 -Anions such as, onium cations such as ammonium, sulfonium, phosphonium, organic phosphorus compounds such as triphenylphosphine and 1,2-bis(diphenylphosphino)ethane, cyclopentadienyl (Cp) group, pentamethylcyclopentadienyl (Cp * ) group, olefins such as cyclooctadiene (COD) group, cyclooctatriene (COT) group, norbornene group, norbornadiene group, α,β-unsaturated ketones such as dibenzylideneacetone, acyl groups such as acetyl group, benzoyl group, β-diketones such as acetylacetone (acac), β-ketoesters such as ethyl acetoacetate, amines such as alkylamine, alkylenediamine, aniline, pyridine, or alkoxy groups can be mentioned. Among them, carbonyl (CO), halide ion, cyclopentadienyl (Cp) group, triphenylphosphine, dibenzylideneacetone are preferable. The ligand may be a monodentate ligand or a polydentate ligand having two or more coordination sites.

[0068] The counter ion is not particularly limited, and examples include halide ions, cyanide ions, carbonates, and anions such as PF6 - , BF4 - , NO3 - , BPh4 - , ClO4 - and onium cations such as ammonium, sulfonium, phosphonium. Among them, Cl - is more preferable.

[0069] As the metal compound capable of catalyzing the [2+2+2] cycloaddition reaction, cyclopentadienylcobalt(I) dicarbonyl, tetrakis(triphenylphosphine)palladium(0), tris(dibenzylideneacetone)dipalladium(0), tris(triphenylphosphine)rhodium(I) chloride are particularly preferable.

[0070] Metal compounds may be used after being diluted by dissolving or dispersing them in a solvent as needed. Any known solvent may be used as such, for example, alcohols such as methanol, ketones such as acetone, hydrocarbon solvents such as hexane, toluene, and xylene, halogenated hydrocarbon solvents such as methylene chloride, chloroform, and 1,2-dichloroethane, esters such as ethyl acetate, and esters with trimethylsilyl groups encapsulated at both ends and a kinematic viscosity of 10 to 50,000 mmHg at 25°C. 2 Examples include polysiloxanes such as dimethylpolysiloxane with a viscosity of 1 / s. In particular, those with a kinematic viscosity of 10,000 to 50,000 mmHg at 25°C. 2 Dispersing or diluting a metal compound in dimethylpolysiloxane at 0 / s can suppress the separation and sedimentation of the metal compound during storage.

[0071] The concentration of the metal compound in the solvent (catalyst concentration) can be set as needed; for example, it can be 0.01 to 10% by mass, preferably 0.1 to 5% by mass, based on the mass of the central metal. The desired composition can be prepared by adding the diluent in an amount that corresponds to the amount of metal compound capable of catalyzing the [2+2+2] cycloaddition reaction described later.

[0072] The amount of metal compound capable of catalyzing the [2+2+2] cycloaddition reaction should be an effective amount as a catalyst, i.e., an effective amount necessary to promote the curing reaction and cure the curable silicone composition of the present invention. Preferably, the amount is 0.1 to 10,000 ppm, more preferably 1 to 5,000 ppm, and even more preferably 10 to 3,000 ppm, based on the mass of the central metal atoms relative to the entire composition. If the amount of catalyst is above the lower limit, a catalytic effect is obtained, and if it is below the upper limit, the catalytic effect is sufficient and economical.

[0073] Furthermore, component (C) is used in the first solution and is not contained in the second solution.

[0074] [(D) component] The curable silicone composition of the present invention may optionally contain an inorganic or organic filler as component (D). Component (D) can impart various properties to the curable silicone composition of the present invention, such as thermal conductivity, heat resistance, reinforcement, conductivity, and design properties. Preferably, the filler is made of at least one material selected from the group consisting of metals, metal oxides, metal hydroxides, metal nitrides, metal carbides, allotropes of carbon, resins, dyes, and pigments. Examples include metals such as aluminum, silver, copper, and metallic silicon; metal oxides such as aluminum oxide (alumina), zinc oxide, magnesium oxide, silicon dioxide, cerium oxide, and iron oxide; metal hydroxides such as aluminum hydroxide and cerium hydroxide; metal nitrides such as aluminum nitride and boron nitride; metal carbides such as silicon carbide; diamond, graphite, and caramel. Examples include von nanotubes, allotropes of carbon such as graphene, resins such as silicone resin powder, dyes such as indigo, and pigments such as red iron oxide. To impart thermal conductivity to the composition, aluminum, silver, alumina, zinc oxide, and aluminum nitride are preferred. To impart heat resistance, cerium oxide, cerium hydroxide, and iron oxide are preferred. To impart reinforcing properties, silicon dioxide such as hydrophobic fumed silica is preferred. To impart conductivity, silver, copper, and allotropes of carbon are preferred. To impart smoothness, silicone resin powder is preferred. To impart design appeal, dyes and pigments such as indigo and red iron oxide are preferred.

[0075] The average particle size of the filler is preferably 500 μm or less, more preferably 300 μm or less, and even more preferably 150 μm or less, as this results in a more uniform composition. Furthermore, a particle size of 0.01 μm or more, particularly 0.1 μm or more, is preferable. The average particle size can be determined, for example, as the volume average value (or median diameter) in particle size distribution measurement by laser diffraction. The shape of the filler is not particularly limited and can be spherical, irregular, needle-shaped, plate-shaped, etc.

[0076] The amount of component (D) should be in the range of 5,000 parts by mass or less, preferably 3,000 parts by mass or less, and more preferably 2,000 parts by mass or less, relative to 100 parts by mass of the total of components (A) and (B). This ensures that the viscosity is not too high, making it easy to handle and resulting in a uniform composition. When component (D) is added, it is preferable that the amount be 0.1 parts by mass or more, and particularly 1 part by mass or more.

[0077] [(E) component] The curable silicone composition of the present invention may contain hydrolyzable organopolysiloxanes, various modified silicones, or hydrolyzable organosilanes for the purpose of improving the filling properties of the filler or imparting adhesion to the composition. Furthermore, a solvent may be added to adjust the viscosity of the composition. In addition, conventionally known antioxidants such as 2,6-di-tert-butyl-4-methylphenol may be included as needed to prevent deterioration of the curable silicone composition. Furthermore, flame retardants, anti-settling agents, or thixotropic agents may be added as needed. When these are added, the amount is preferably 0.1 to 10.0% by mass of the total composition.

[0078] [Method for producing silicone composition] The method for producing the curable silicone composition according to the present invention will now be described. The method for producing the curable silicone composition according to the present invention is not particularly limited, but is a two-component curable silicone composition comprising a first liquid containing component (A) and component (C) above, but not component (B), and a second liquid containing component (B) above, but not component (C). In other words, the first liquid contains components (A) and (C) above, and optionally component (D) and other components in addition thereto, and the second liquid contains component (B) above, and optionally component (A) and component (D) in addition thereto, and the curable silicone composition of each liquid is prepared by mixing them.

[0079] The mixing apparatus used to prepare the first and second liquids described above may include, for example, a mixer such as Awatori Rentaro (registered trademark of Shinky Co., Ltd.), Trimix, Twinmix, Planetary Mixer (all registered trademarks of mixers manufactured by Inoue Seisakusho Co., Ltd.), Ultra Mixer (registered trademark of mixers manufactured by Mizuho Industries Co., Ltd.), or Hibiscus Disper Mix (registered trademark of mixers manufactured by Tokushu Kika Kogyo Co., Ltd.), or by hand mixing using a spatula or the like, and the mixing is performed at 25°C for typically 3 minutes to 24 hours, preferably 5 minutes to 12 hours, and particularly preferably 10 minutes to 6 hours. Degassing may also be performed during mixing.

[0080] In the composition of the present invention, the mixing ratio of the first liquid and the second liquid is preferably approximately equal by mass. Specifically, the ratio of the first liquid to the second liquid is preferably in the range of 1:0.5 to 1:2, more preferably 1:0.75 to 1:1.25, even more preferably 1:0.9 to 1:1.1, and particularly preferably in the range of 1:0.95 to 1:1.05. The mixing device for the first liquid and the second liquid is not limited to a static mixer or other stationary mixer, but may be a known mixer such as a planetary mixer or a paddle mixer.

[0081] The curable silicone composition of the present invention has an absolute viscosity, measured at 25°C, preferably 0.1 to 1,000 Pa·s, more preferably 1 to 700 Pa·s, and even more preferably 5 to 500 Pa·s. When the viscosity is 0.1 Pa·s or higher, workability is improved, such as good shape retention. When the viscosity is 1,000 Pa·s or lower, workability is improved, such as easy dispensing and application. The above viscosity can be obtained by adjusting the blending of each component described above. In the present invention, the absolute viscosity is the value measured at 25°C using a Malcolm viscometer (rotor A at 10 rpm, shear rate 6 [1 / s]).

[0082] The silicone cured product of the present invention is obtained by curing the above-mentioned curable silicone composition. The method for producing this cured silicone product is characterized by comprising the steps of mixing a two-component curable silicone composition consisting of a first liquid containing component (A) and component (C) above, but not component (B), and a second liquid containing component (B) above, but not component (C), and curing the resulting mixture.

[0083] The curing conditions for curing the curable silicone composition of the present invention are not particularly limited, but the heating temperature is usually 0 to 200°C, preferably 10 to 150°C, and particularly preferably 20 to 100°C. In particular, electrical and electronic components and modules including circuit boards on which these are mounted can be cured at 100°C or below, where high-temperature heating is undesirable.

[0084] The curing time is typically 3 minutes to 72 hours, preferably 5 minutes to 48 hours, and particularly preferably 10 minutes to 24 hours. The properties of the curable silicone composition after curing are not particularly limited and include gel-like, low-hardness rubber-like, and high-hardness rubber-like forms.

[0085] The silicone cured product of the present invention is an elastic material, and since silicone itself has excellent heat resistance and chemical resistance, it is useful as a silicone elastomer used as a coating agent, sealant, and encapsulant for semiconductor devices.

[0086] The curable silicone composition of the present invention is a liquid silicone composition when used, and curing proceeds under mild conditions in the presence of a catalyst, making it possible to form a silicone elastomer.

[0087] In this invention, a [2+2+2] cycloaddition reaction of alkynes, in which carbon-carbon bonds are formed between multiple bonds using a metal catalyst, is employed as the curing system. The [2+2+2] cycloaddition reaction is a reaction that forms an aromatic ring from three triple bonds, and it is a very useful reaction as it does not produce any by-product gases. Furthermore, by appropriately selecting the catalyst, it is possible to achieve both the desired workability and curing characteristics.

[0088] In particular, the composition of the present invention hardens by a catalytic [2+2+2] cycloaddition reaction, and therefore exhibits superior hardening properties compared to conventional addition reactions using radicals, addition reactions by hydrosilylation, and condensation reactions, resulting in a cured product with excellent properties. Specifically, (I) unlike radical addition reactions, high temperatures are not required for the generation of the initiating species, and hardening can be performed at room temperature or by heating. It is also less susceptible to hardening inhibition by oxygen, resulting in excellent surface hardening properties. (II) The addition reaction mechanism differs from hydrosilylation, making it less prone to hardening failure even if sulfur, phosphorus, nitrogen compounds, water, or organometallic salts are mixed in or come into contact with it. (III) Unlike condensation reactions, hardening can be performed at room temperature without utilizing moisture in the air. It does not generate gas or undergo volume shrinkage during hardening and exhibits excellent deep hardening properties, thus possessing unprecedented and superior hardening characteristics.

[0089] The curable silicone composition of the present invention can be cured under mild conditions of 100°C or less, even when using a catalyst that is stable at room temperature. Therefore, it can be cured even when using components that are sensitive to heat and cannot be exposed to high temperatures during mounting, making it highly valuable as a material used around electrical and electronic components and semiconductor elements. Curing can be achieved smoothly even under milder conditions by using a highly active catalyst. [Examples]

[0090] The present invention will be described in more detail below with reference to examples and comparative examples, but the present invention is not limited to the following examples. In the following, the kinematic viscosity at 25°C is the value measured as described above, the catalyst concentration is based on the mass of the central metal atom relative to the entire composition, the average particle size is the volume-based average value obtained by particle size distribution measurement using laser diffraction, and in the structural formulas described in the examples, Me represents a methyl group.

[0091] First, the following components were prepared to create the curable silicone composition of the present invention. (A) component A-1: Both ends are sealed with ethynyl groups, and the kinematic viscosity at 25°C is 600 mmHg. 2 / s Dimethylpolysiloxane A-2: Both ends are sealed with trimethylsilyl groups, and the kinematic viscosity at 25°C is 500 mmHg. 2 / s Dimethylpolysiloxane (B) Component B-1: The kinematic viscosity at 25°C is 450 mm², as shown in formula (4) below. 2 / s organopolysiloxane [ka] B-2: The kinematic viscosity at 25°C is 80 mm, as shown in formula (5) below. 2 / s organopolysiloxane [ka] B-3: The kinematic viscosity at 25°C is 140 mm², as shown in formula (6) below. 2 / s organopolysiloxane [ka] (C) Component C-1: A solution of Tris(dibenzylideneacetone)dipalladium(0) dissolved in methylene chloride (catalyst concentration: 5% by mass) C-2: Tris(dibenzylideneacetone)dipalladium(0) is capped at both ends with trimethylsilyl groups, and has a kinematic viscosity of 50,000 mmHg at 25°C. 2 Solution of dimethylpolysiloxane at 1 / s (catalyst concentration: 5% by mass) (D) Component D-1: Aluminum oxide powder with an average particle size of 10 μm D-2: Zinc oxide powder with an average particle size of 0.4 μm (E) Component E-1: Hydrolyzable organosilane represented by the following formula (7) C 10 H 21 Si(OMe)3(7)

[0092] [Examples 1-4, Comparative Examples 1 and 2] Preparation of curable silicone compositions [1] Components (A) to (C) above were mixed by hand using a spatula in the amounts shown in Table 1 below to prepare a curable silicone composition. The properties of the obtained silicone composition were confirmed when cured under the temperature conditions shown in Table 1 below. The results are shown in Table 1.

[0093] [Table 1]

[0094] From the above results, the silicone compositions of Examples 1 to 4 of the present invention can be cured into a rubbery state within 24 hours at a relatively low temperature of less than 100°C. Comparative Example 1 shows that when the organopolysiloxane component (B), which satisfies the requirements of the present invention, is not included, the curability at low temperatures is significantly low. Furthermore, Comparative Example 2 shows that when components (B) and (C) coexist in the first liquid, the storage stability is poor, and the composition hardens during storage at room temperature, making it unsuitable for storage at room temperature. Therefore, the two-component curable silicone composition of the present invention has the advantage that, by mixing a metal catalyst capable of catalyzing a [2+2+2] cycloaddition reaction in the first liquid and an organopolysiloxane having a specific structure in the second liquid, the first liquid and the second liquid can be cured into a rubbery state at a low temperature of 100°C or less when mixed, and each liquid can be stored at room temperature.

[0095] [Examples 5-10, Comparative Examples 3, 4] Preparation of curable silicone compositions [2] Components (A), (B), (C), (D), and (E) above were mixed in the amounts shown in Tables 2 and 3 below using Awatori Rentaro (manufactured by Shinky Co., Ltd.) to prepare a curable silicone composition. The properties of the obtained two-component curable silicone composition were confirmed when cured under the temperature conditions shown in Tables 2 and 3 below. The results are shown in Tables 2 and 3.

[0096] [Table 2]

[0097] [Table 3]

[0098] From the above results, it can be seen that the silicone compositions of Examples 5 to 10 of the present invention can be cured into a rubbery state within 48 hours at a relatively low temperature of less than 100°C. From Examples 5 to 8, it can be seen that component (A) satisfies the requirements with either (A-1) alone or (A-2) alone. From Examples 9 and 10, it can be seen that component (A) satisfies the requirements even with a mixture of (A-1) and (A-2). Comparative Example 3 shows that when component (B), which satisfies the requirements of the present invention, does not contain organopolysiloxane, the curability at low temperatures is significantly low. Furthermore, from Comparative Example 4, it can be seen that when components (B) and (C) coexist in the first liquid, the storage stability is poor and it hardens during storage at room temperature, making it impossible to store at room temperature. Therefore, even when the two-component curable silicone composition of the present invention contains a large amount of filler, by mixing a metal catalyst capable of catalyzing a [2+2+2] cycloaddition reaction in the first liquid and an organopolysiloxane having a specific structure in the second liquid, the composition can be cured into a rubbery state at a low temperature of 100°C or less when the first and second liquids are mixed, and each liquid can be stored at room temperature.

[0099] This specification includes the following inventions:

[0100] [1]: A two-component curable silicone composition, (A) Organopolysiloxanes comprising the following components (A-1) and / or (A-2), (A-1) Organopolysiloxanes having at least one alkynyl group or nitrile group in one molecule, and (A-2) The average composition formula below (R 1 3SiO 1 / 2 ) a (R 1 2SiO 2 / 2 ) b (R 1 SiO 3 / 2 ) c (SiO 4 / 2 ) d (1) (In the formula, R1 Each of these is an independently unsubstituted or substituted monovalent hydrocarbon group, where a is a number of 2 or more, and a+b+c+d is a number of 2 or more. However, in the case of a linear organopolysiloxane compound, a=2, b is between 2 and 1,200, and c=d=0. In the case of a branched organopolysiloxane compound, a is a number of 2 or more, b is between 2 and 1,200, and c or d is 1 or more. The kinematic viscosity at 25°C, as shown by [formula], is between 1 and 100,000 mm². 2 / s organopolysiloxane, and (B) Organopolysiloxane compounds having substituents represented by the following general formula (2) in the molecule, [ka] (In the formula, R 2 R is independently a substituted or unsubstituted monovalent hydrocarbon group or hydrogen atom, 3 R is an independently substituted or unsubstituted divalent hydrocarbon group. 4 is a divalent linking group. ) and, (C) Metal compounds capable of catalyzing [2+2+2] cycloaddition reactions A two-component curable silicone composition characterized in that, among the above-mentioned components, the first liquid contains (A) and (C) but does not contain (B), and the second liquid contains component (B) but does not contain component (C). [2]: R in the general formula (2) 3 A two-component curable silicone composition according to [1], characterized in that the group is a methylene group. [3]: R in the general formula (2) 2 A two-component curable silicone composition according to [1], characterized in that the atom is a hydrogen atom. [4]: The two-component curable silicone composition according to [1], characterized in that the (B) component is an organopolysiloxane compound having an average of two or more substituents represented by the general formula (2) in one molecule. [5]: The two-component curable silicone composition according to any one of [1] to [4], further characterized in that (D) contains 0.1 to 5,000 parts by mass of at least one inorganic or organic filler with respect to 100 parts by mass of the total of components (A) and (B). [6]: The two-component curable silicone composition according to [5], characterized in that the (D) component is a filler made of one or more materials selected from the group consisting of metals, metal oxides, metal hydroxides, metal nitrides, metal carbides, allotropes of carbon, resins, dyes, and pigments. [7]: A cured silicone product obtained by curing a two-component curable silicone composition described in any of [1] to [4]. [8]:A cured silicone product obtained by curing the two-component curable silicone composition described in [5].

[0101] It should be noted that the present invention is not limited to the embodiments described above. The embodiments described above are illustrative, and any configuration that is substantially identical to the technical idea described in the claims of the present invention and achieves similar effects is included within the technical scope of the present invention.

Claims

1. A two-component curable silicone composition, (A) Organopolysiloxanes comprising the following components (A-1) and / or (A-2), (A-1) Organopolysiloxane having at least one alkynyl group or nitrile group in one molecule, and (A-2) The following average composition formula (1) (R １ ３ SiO １／２ ) ａ (R １ ２ SiO ２／２ ) ｂ (R １ SiO ３／２ ) ｃ (SiO ４／２ ) ｄ (1) (In the formula, R １ Each of these is an independent unsubstituted or substituted monovalent hydrocarbon group, where a is a number of 2 or more, and a+b+c+d is a number of 2 or more. However, in the case of a linear organopolysiloxane compound, a=2, b is between 2 and 1,200, and c=d=0. In the case of a branched organopolysiloxane compound, a is a number of 2 or more, b is between 2 and 1,200, and c or d is 1 or more. The kinematic viscosity at 25°C, as shown by [formula], is between 1 and 100,000 mm². ２ / s organopolysiloxane, and, (B) Organopolysiloxane compounds having substituents represented by the following general formula (2) in the molecule, 【Chemistry 1】 (In the formula, R ２ R is independently a substituted or unsubstituted monovalent hydrocarbon group or hydrogen atom, ３ R is an independently substituted or unsubstituted divalent hydrocarbon group. ４ is a divalent linking group. ) and, (C) Metal compounds capable of catalyzing [2+2+2] cycloaddition reactions A two-component curable silicone composition characterized in that, among the above-mentioned components, the first liquid contains (A) and (C) but does not contain (B), and the second liquid contains component (B) but does not contain component (C).

2. In the above general formula (2), R ３ The two-component curable silicone composition according to claim 1, characterized in that the group is a methylene group.

3. In the above general formula (2), R ２ The two-component curable silicone composition according to claim 1, characterized in that the atom is a hydrogen atom.

4. The two-component curable silicone composition according to claim 1, characterized in that the (B) component is an organopolysiloxane compound having an average of two or more substituents represented by the general formula (2) in one molecule.

5. Furthermore, the two-component curable silicone composition according to any one of claims 1 to 4, characterized in that (D) contains 0.1 to 5,000 parts by mass of at least one inorganic or organic filler with respect to 100 parts by mass of the total of components (A) and (B).

6. The two-component curable silicone composition according to claim 5, characterized in that the (D) component is a filler made of one or more materials selected from the group consisting of metals, metal oxides, metal hydroxides, metal nitrides, metal carbides, allotropes of carbon, resins, dyes, and pigments.

7. A cured silicone product obtained by curing a two-component curable silicone composition according to any one of claims 1 to 4.

8. A cured silicone product obtained by curing the two-component curable silicone composition described in claim 5.

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