Curable compositions, cured products, and heat dissipation components

Abstract

The object of the present invention is to provide a curable composition that has excellent dispersibility and exhibits excellent tensile strength and adhesive strength when cured. [Solution] A curable composition comprising a polyether polyol, a polyisocyanate, a metal-organic compound, and an inorganic filler, wherein the metal-organic compound is at least one selected from the group consisting of titanium alkoxide, aluminum alkoxide, and zinc acylate; a cured product of the curable composition; and a heat dissipation member comprising the cured product.

Description

Technical Field

[0001] The present invention relates to a curable composition, a cured product of the curable composition, and a heat radiating member including the cured product.

Background Art

[0002] Electronic devices are becoming more highly integrated and faster year by year, and accordingly, the demand for heat dissipation materials for heat countermeasures is increasing. If heat dissipation is insufficient, the normal operation of electronic devices and the like may be hindered, and there is a risk of causing deterioration, failure, and damage. As a material exhibiting heat dissipation properties, a polyurethane resin composition containing a hydroxyl group-containing compound containing polybutadiene polyol, a specific polyisocyanate compound, and an inorganic filler is known (Patent Document 1).

Prior Art Documents

Patent Documents

[0003]

Patent Document 1

Summary of the Invention

Problems to be Solved by the Invention

[0004] However, fillers such as inorganic fillers tend to aggregate, and there is a problem that the dispersibility of the filler is poor in a curable composition which is a mixture of monomers and fillers. In addition, depending on the combination of monomers and base materials, there is a problem that the strength of the cured product and the adhesive strength with metal decrease.

[0005] An object of the present invention is to provide a curable composition having excellent dispersibility and excellent tensile strength and adhesive strength when formed into a cured product.

Means for Solving the Problems

[0006] As a result of intensive studies, the present inventors have reached the present invention. The present invention relates to a curable composition comprising a polyether polyol, a polyisocyanate, a metal-organic compound, and an inorganic filler, wherein the metal-organic compound is at least one selected from the group consisting of titanium alkoxide, aluminum alkoxide, and zinc acylate. [Effects of the Invention]

[0007] According to the present invention, it is possible to provide a curable composition that has excellent dispersibility and excellent tensile strength and adhesive strength when cured. [Modes for carrying out the invention]

[0008] The curable composition of the present invention comprises a polyether polyol, a polyisocyanate, a metal-organic compound, and an inorganic filler. The curable composition of the present invention is also a polyurethane resin-forming composition.

[0009] Because the curable composition of the present invention contains a polyether polyol as an essential component, it has low viscosity and good handling properties. As the polyether polyol, polyoxyalkylene polyols are preferred from the viewpoint of reducing the viscosity of the curable composition. Preferred examples of polyoxyalkylene polyols include polyethylene glycol, polypropylene glycol, polyoxyethylene-oxypropylene glycol, polytetramethylene glycol, polyoxytetramethylene-oxyethylene glycol, polyoxytetramethylene-oxypropylene glycol, polyhexamethylene ether glycol, and polyoxypropylene glyceryl ether. Polyoxyalkylene polyols can be obtained from the market as Sannix PK-400 [manufactured by Sanyo Chemical Industries, Ltd.], etc. Polyether polyols may be used individually or in combination of two or more types.

[0010] From the viewpoint of the flexibility of the resulting curable composition, the polyether polyol is preferably a polyoxyalkylene polyol, and more preferably a polyoxyalkylenediol.

[0011] From the viewpoint of reducing viscosity, the number-average molecular weight (Mn) of the polyether polyol is preferably 100 to 10000, more preferably 150 to 3000, and most preferably 200 to 2000. The measurement conditions for Mn in polyether polyols are as follows: Equipment: High-temperature gel permeation chromatograph ["Alliance GPC V2000", manufactured by Waters Japan Ltd.] Detection device: Refractive index detector Solvent: Orthodichlorobenzene Reference material: Polystyrene Sample concentration: 3 mg / ml Column stationary phase: PLgel 10 μm, MIXED-B x 2 in series [Polymer Laboratories] Column temperature: 135℃

[0012] In the curable composition of the present invention, the content of polyether polyol is not particularly limited, but is preferably 3 to 20% by weight, and more preferably 5 to 10% by weight, based on the total weight of the curable composition.

[0013] The curable composition of the present invention may contain polyols other than the polyether polyols described above. Examples of polyols other than polyether polyols include polyester polyols, polycarbonate polyols, and polyolefin polyols. Polyols other than polyether polyols may be used individually or in combination of two or more types.

[0014] Examples of polyester polyols include condensates of polyols [such as the aforementioned polyether polyols, aliphatic diols, trivalent or higher aliphatic polyols, alicyclic polyols, and alkylene oxide adducts of alicyclic polyols (representing ethylene oxide, propylene oxide, 1,2-, 1,3-, 2,3-, or 1,4-butylene oxide, and sometimes abbreviated as AO below)] and polycarboxylic acids, and these can be obtained from the market as Kuraray Polyol P-2010 [(manufactured by Kuraray Co., Ltd.)].

[0015] Examples of aliphatic diols include those having 2 to 20 carbon atoms. The number of carbon atoms in the aliphatic diol is preferably 2 to 10, and more preferably 2 to 5.

[0016] Examples of trivalent or higher aliphatic polyols include trivalent or higher aliphatic polyols with 3 to 20 carbon atoms (such as glycerin and pentaerythritol), with glycerin being preferred.

[0017] Examples of alicyclic polyols include alicyclic polyols having 4 to 16 carbon atoms (such as 1,4-cyclohexanediol, 1,4-cyclohexanedimethanol, and hydrogenated bisphenol A).

[0018] Examples of AO adducts of alicyclic polyols include compounds obtained by adding AO to the aforementioned alicyclic polyols. The AO used can be the same as those exemplified in the description of polyester polyols, and the preferred AOs are also the same.

[0019] Polycarboxylic acids include chain-like aliphatic polycarboxylic acids with 2 to 20 carbon atoms [oxalic acid, malonic acid, dipropylmalonic acid, succinic acid, 2,2-dimethylsuccinic acid, glutaric acid, 2-methylglutaric acid, 2,2-dimethylglutaric acid, 2,4-dimethylglutaric acid, 3-methylglutaric acid, 3,3-dimethylglutaric acid, 3-ethyl-3-methylglutaric acid, adipic acid, 3-methyladipic acid, pimelic acid, 2,2,6,6-tetramethylpimelic acid, azelaic acid, sebacic acid, undecanediic acid, dodecanediic acid, pentadecanediic acid, tetradecanediic acid, heptade Examples include candioic acid, octadecanediic acid, nonadecanedioic acid, and eicosanedioic acid; alicyclic polycarboxylic acids with 5 to 20 carbon atoms [cyclopropanediic acid, 1,4-cyclohexanedicarboxylic acid, cyclohexenedicarboxylic acid, dicyclohexyl-4,4'-dicarboxylic acid, and camphoric acid, etc.]; and aromatic polycarboxylic acids with 8 to 20 carbon atoms [terephthalic acid, isophthalic acid, 2-methylterephthalic acid, 4,4-stilbendicarboxylic acid, naphthalenedicarboxylic acid, 4,4-biphenyldicarboxylic acid, orthophthalic acid, and diphenyl etherdicarboxylic acid, etc.].

[0020] Examples of polycarbonate polyols include reaction products of polyols [such as the aforementioned polyether polyols, aliphatic diols, trivalent or higher aliphatic polyols, alicyclic polyols, AO adducts of alicyclic polyols, etc.] with phosgene, etc., and can be obtained from the market as Kuraray Polyol C-590, Kuraray Polyol C-2090 [both manufactured by Kuraray Co., Ltd.], etc.

[0021] Examples of polyolefin polyols include polybutadiene polyols and hydrogenated polybutadiene diols.

[0022] From the viewpoint of the tensile strength of the cured product, it is preferable that the polyol has at least two hydroxyl groups on average per molecule.

[0023] When the curable composition of the present invention contains a polyether polyol and a polyol other than a polyether polyol, the content of the polyol other than a polyether polyol is preferably 100 to 150 parts by weight per 100 parts by weight of the polyether polyol.

[0024] The curable composition of the present invention contains a polyisocyanate. It is not particularly limited to any compound having two or more isocyanate groups in its molecule. Examples of polyisocyanates include aromatic polyisocyanates, aliphatic polyisocyanates, alicyclic polyisocyanates, aromatic aliphatic polyisocyanates, and modified polyisocyanates. One type of polyisocyanate or two or more types may be used in combination.

[0025] Examples of aromatic polyisocyanates include aromatic polyisocyanates having 8 to 22 carbon atoms, preferably 1,3- or 1,4-phenylenediisocyanate, 2,4- or 2,6-tolylenediisocyanate (TDI), 4,4'- or 2,4'-diphenylmethanediisocyanate (MDI), m- or p-isocyanatophenylsulfonyl isocyanate, 4,4'-diisocyanatobiphenyl, 3,3'-dimethyl-4,4'-diisocyanatobiphenyl, 3,3'-dimethyl-4,4'-diisocyanatodiphenylmethane, 1,5-naphthylenediisocyanate, m- or p-xylylenediisocyanate (XDI), and α,α,α',α'-tetramethylxylylenediisocyanate (TMXDI).

[0026] Examples of aliphatic polyisocyanates include chain-like aliphatic polyisocyanates having 4 to 20 carbon atoms, and preferably include ethylene diisocyanate, tetramethylene diisocyanate, hexamethylene diisocyanate, dodecamethylene diisocyanate, 2,2,4-trimethylhexamethylene diisocyanate, and lysine diisocyanate.

[0027] Examples of alicyclic polyisocyanates include alicyclic polyisocyanates having 6 to 17 carbon atoms, preferably isophorone diisocyanate (IPDI), 4,4-dicyclohexylmethane diisocyanate, cyclohexylene diisocyanate, methylcyclohexylene diisocyanate, bis(2-isocyanatoethyl)-4-cyclohexene-1,2-dicarboxylate, and 2,5- or 2,6-norbornane diisocyanate. Alicyclic polyisocyanates can be obtained from the market as Desmodule I [manufactured by Sumika Covestrourethane Co., Ltd.], etc.

[0028] Examples of modified polyisocyanates include trimers of polyisocyanates (such as the aliphatic polyisocyanates, alicyclic polyisocyanates, and aromatic polyisocyanates mentioned above). Specific examples include isocyanurates of 1,6-hexamethylene diisocyanate, TDI, MDI, and IPDI. For example, isocyanurates of hexamethylene diisocyanate can be obtained from the market as Duranate TLA-100, Duranate TUL-100 [manufactured by Asahi Kasei Corporation], etc.

[0029] From the viewpoint of excellent moldability, isocyanurates of at least one isocyanate selected from the group consisting of aromatic polyisocyanates, aliphatic polyisocyanates, and alicyclic polyisocyanates are preferred among polyisocyanates. One type of polyisocyanate may be used alone, or two or more types may be used in combination.

[0030] In the curable composition of the present invention, the content of polyisocyanate is not particularly limited, but is preferably 4 to 20% by weight, and more preferably 5 to 10% by weight, based on the total weight of the curable composition.

[0031] The total content ratio of polyols and polyisocyanates in the curable composition of the present invention is not particularly limited and can be adjusted as appropriate depending on the compound used, but it is preferably 3 to 30% by weight, and more preferably 3 to 20% by weight, based on the total weight of the curable composition.

[0032] In the curable composition of the present invention, the molar ratio of isocyanate groups of the polyisocyanate to hydroxyl groups of the polyether polyol (total number of moles of isocyanate groups of the polyisocyanate / total number of moles of hydroxyl groups of the polyether polyol) (hereinafter also simply referred to as the isocyanate index) is preferably 0.8 to 1.2. When the isocyanate index is within the above range, the curability of the curable composition and the flexibility of the cured product are good.

[0033] The curable composition of the present invention contains a metal-organic compound. The metal-organic compound is at least one selected from the group consisting of titanium alkoxide, aluminum alkoxide, and zinc acylate. Of these, titanium alkoxide and aluminum alkoxide are preferred. The curable composition of the present invention contains a metal-organic compound, which is believed to improve adhesive strength by forming a chemical or physical bond at the interface between the adhesive surface and the resin component, thereby improving the interfacial adhesion between the two.

[0034] Examples of titanium alkoxides include compounds represented by the following general formula (2). Ti(OR 1 ) a (L 1 ) b ...(2) In the general formula (2) above, a or b is an integer from 1 to 3, and a+b=4, R 1 L represents a hydrocarbon group having 3 to 18 carbon atoms, which may have heteroatoms. 1is a ligand selected from a dialkyl phosphite, a dialkyl diphosphate, an aryl sulfonate or an aliphatic carboxylate having 8 to 22 carbon atoms, and the two alkyl groups of the dialkyl phosphite and the dialkyl diphosphate may each independently be an alkyl having 8 to 22 carbon atoms or an alkenyl having 8 to 22 carbon atoms, and the hydrogen atom of the aryl of the aryl sulfonate may be substituted with an alkyl group having 8 to 22 carbon atoms or an alkenyl group having 8 to 22 carbon atoms.

[0035] Examples of the aluminum alkoxide include a compound represented by the following general formula (3). Al(OR 1 )2(L 2 )···(3) In the general formula (3), R 1 represents a hydrocarbon group having 3 to 18 carbon atoms which may have a hetero atom, and L 2 is an alkyl having 8 to 22 carbon atoms or an alkenyloxy-substituted β-dicarbonyl ligand having 8 to 22 carbon atoms.

[0036] Specifically, these include titanium tetramethoxide, titanium tetraethoxide, titanium tetraisopropoxide, titanium tetran-butoxide, titanium tetratertiary butoxide, titanium butoxide dimer, titanium tetraoctyloxide, titanium tetra(2-ethylhexyloxide), tertiary amyl titanate, tetrakis(octadecyloxy)titanium, isopropyl triisostearoyl titanate, isopropyl tris(dioctyl pyrophosphate) titanate, isopropyl tri(N-aminoethyl-aminoethyl) titanate, tetraoctylbis(di-tridecylphosphate) titanate, and tetra(2,2-diallyloxymethyl-1-butyl) Titanium alkoxide compounds such as bis(di-tridecyl)phosphite titanate, bis(octyl pyrophosphate)oxyacetate titanate, bis(dioctyl pyrophosphate)ethylene titanate, isopropyltrioctanoyl titanate, isopropyl dimethacrylate isostearoyl titanate, isopropyl toridodecylbenzenesulfonyl titanate, isopropyl isostearoyl diacrylic titanate, isopropyl tri(dioctyl sulfate) titanate, isopropyl tricumylphenyl titanate, tetraisopropylbis(dioctyl phosphate) titanate, and isopropyl tris(dioctyl pyrophosphate) titanate; Examples include aluminum trimethoxide, aluminum triethoxide, aluminum triisopropoxide, aluminum tributoxide, aluminum secondary butoxide, and aluminum alkoxide compounds such as alkyl acetacetate aluminum diisopropylate.

[0037] Examples of zinc acylates include zinc butyrate, zinc caproate, zinc caprylate, zinc pelargonate, zinc caprate, zinc undecanoate, zinc laurate, zinc myristate, zinc palmitate, zinc stearate, zinc 12-hydroxystearate, zinc arachinate, zinc behenate, zinc lignocerate, zinc cerotinate, zinc montanate, and zinc cyanurate [Starfine F-10 (manufactured by Nissan Chemical Corporation)].

[0038] Furthermore, the metal-organic compound may also include metal-organic compounds other than the titanium alkoxide, aluminum alkoxide, and zinc acylate mentioned above. Examples include metal alkoxides, metal chelates, and metal acylates.

[0039] Examples of metal alkoxides include compounds represented by the following general formula (4). (R 1 O) n M(OR 2 ) m ...(4) In the general formula (4) above, M represents one metal atom selected from the group consisting of tin, zirconium, and iron, and R 1 , R 2 n represents a hydrocarbon group having 3 to 18 carbon atoms, which may have heteroatoms; n represents an integer from 1 to 4; m represents an integer of 0 or more; and n+m represents the valence of M. Examples of the heteroatoms include oxygen, nitrogen, sulfur, or phosphorus atoms.

[0040] Specifically, tin alkoxide compounds such as tetramethoxystannane, tetraethoxystannane, triphenoxymethylstannane, and 1,2-bis(triethoxystannane)ethane; Zirconium tetra-n-propoxide, zirconium-n-propoxide, zirconium-n-butoxide, neoalkoxytris neodecanoyl zirconate, neoalkoxytris (dodecyl)benzenesulfonyl zirconate, neoalkoxytris (dioctyl) phosphate zirconate, neoalkoxytris (dioctyl) pyrophosphate zirconate, neoalkoxytris (ethylenediamino) ethyl zirconate, neoalkoxytris (m-amino)phenyl zirconate Tetra(2,2-diallyloxymethyl)butyl, di(ditridecyl)phosphytozirconate, neopentyl(diallyl)oxy, trineodecanoylzirconate, neopentyl(diallyl)oxy, tri(dodecyl)benzenesulfonylzirconate, neopentyl(diallyl)oxy, tri(dioctyl)phosphatozirconate, neopentyl(diallyl)oxy, tri(dioctyl)pyrophosphatozirconate, neopentyl(diallyl)oxy, tri(N-ethylenediamino )Ethyl zirconate, neopentyl(diallyl)oxy,tri(m-amino)phenyl zirconate, neopentyl(diallyl)oxy,trimethacrylate zirconate, neopentyl(diallyl)oxy,triacrylic zirconate, dineopentyl(diallyl)oxy,diparaaminobenzoyl zirconate, dineopentyl(diallyl)oxy,di(3-mercapto)propionic zirconate, zirconium(IV)2,2-bis(2-propenolatemethyl)butanolate,cyclodi[2,2- Zirconium alkoxide compounds such as (bis-2-propenolatemethyl)butanolate]pyrophosphat-O,O, neoalkoxytris neodecanoyl zirconate, neoalkoxytris (dodecyl)benzenesulfonyl zirconate, neoalkoxytris (dioctyl)phosphate zirconate, neoalkoxytris (dioctyl)pyrophosphate zirconate, neoalkoxytris (ethylenediamino)ethyl zirconate, and neoalkoxytris (m-amino)phenyl zirconate; Examples include iron(II) methoxide, iron(III) methoxide, iron(II) ethoxide, iron(III) ethoxide, iron(II) isopropoxide, iron(III) isopropoxide, iron(II) 2-ethylhexoxide, iron(III) 2-ethylhexoxide, and other iron alkoxide compounds.

[0041] Examples of metal chelates include compounds in which one or more polydentate ligands L are bonded to one metal atom M selected from the group consisting of titanium, aluminum, zinc, zirconium, and iron.

[0042] Examples of the polydentate ligand L include β-ketoesters such as methyl acetoacetate, ethyl acetoacetate, octyl acetoacetate, oleyl acetoacetate, lauryl acetoacetate, and stearyl acetoacetate, as well as β-diketones such as acetylacetone, 2,4-hexanedione, and benzoylacetone, and triethanolamine. These are ketoenol tautomer compounds, and in the case of polydentate ligand L, the enol may be deprotonated enolates (e.g., acetylacetonate).

[0043] Furthermore, the metal chelate may or may not have one or more monodentate ligands X bonded to a metal atom M. For example, a metal chelate with one central metal atom M is represented by the following general formula (5). M(L)o(X)p ···(5) In the general formula (5) above, o≧1 and p≧0. When o is 2 or more, the o L atoms may be the same ligand or different ligands. When p is 2 or more, the p X atoms may be the same ligand or different ligands. Also, o+p represents the valence of M.

[0044] Examples of the monodentate ligand X include halogen atoms such as chlorine and bromine atoms, acyloxy groups such as pentanoyl, hexanoyl, 2-ethylhexanoyl, octanoyl, nonanoyl, decanoyl, dodecanoyl, and octadecanoyl groups, and alkoxy groups such as methoxy, ethoxy, n-propoxy, isopropoxy, and butoxy groups.

[0045] Specific examples of the aforementioned metal chelates include titanium chelate compounds such as titanium diisopropoxybis(acetylacetonate), titanium tetraacetylacetonate, titanium diisopropoxybis(ethylacetoacetate), titanium di-2-ethylhexoxybis(2-ethyl-3-hydroxyhexoxide), titanium diisopropoxybis(triethanolamine), titanium-1,3-propanedioxybis(ethylacetoacetate), titanium aminoethylaminoethanolate, titanium acetylacetonate, titanium ethylacetoacetate, titanium phosphate compounds, titanium octylene glycolate, and titanium ethylacetoacetate; Zinc chelate compounds such as zinc propoxide and zinc butoxide (excluding zinc acylate); zirconium chelate compounds such as zirconium tetraacetylacetonate, zirconium tributoxyacetylacetonate, zirconium dibutoxybis(acetylacetonate), zirconium tributoxyethylacetoacetate, and zirconium monobutoxyacetylacetonate bis(ethylacetoacetate); Examples include iron chelate compounds such as tris(2,4-pentanedionato)ferrate(III), iron trisacetylacetonate, and tris(2,4-hexanedionato)ferrate(III). Among these, alkylacetacetate aluminum diisopropylate is preferred.

[0046] Examples of metal acylates include compounds represented by the following general formula (6). M(OCOR 3 )q ···(6) In the above general formula (6), M is a metal atom selected from the group consisting of titanium, aluminum, tin, zirconium, and iron, and R 3 is a hydrocarbon group which may have a heteroatom, q is an integer from 1 to 4, and also represents the valence of M. The aforementioned R 3 Examples of heteroatoms include oxygen atoms, nitrogen atoms, sulfur atoms, and phosphorus atoms. Examples of the hydrocarbon groups mentioned above include aliphatic hydrocarbon groups, aromatic hydrocarbon groups, or combinations thereof. Among these, aliphatic hydrocarbon groups are preferred.

[0047] The aliphatic hydrocarbon group may be linear, branched, or cyclic. Specific examples of the aliphatic hydrocarbon group include, for example, linear or branched alkyl groups having 2 to 30 carbon atoms, linear or branched alkenyl groups having 2 to 30 carbon atoms, and linear or branched alkynyl groups having 2 to 30 carbon atoms.

[0048] Examples of the aromatic hydrocarbon group include aryl groups and naphthyl groups. Examples of the aryl group include phenyl groups, tolyl groups, and xylyl groups.

[0049] Specific examples of metal acylates include titanium acylate compounds such as trin-normal butoxytitanium monostearate, diisopropoxytitanium distearate, diisopropoxytitanium diisostearate, (2-normal butoxycarbonylbenzoyloxy)tributoxytitanium, titanium stearate, and n-butyl titanium phosphate; aluminum formate (e.g., aluminum triformate), aluminum acetate, aluminum propionate (e.g., aluminum tripionate), aluminum butyrate (e.g., aluminum tributyrate), and myristic acid. Examples include aluminum acylate compounds such as luminium, aluminum palmitate, and aluminum stearate; zirconium acylate compounds such as zirconium octoate and zirconium stearate; and iron acylates such as iron(II) laurate, iron(III) laurate, iron(II) palmitate, iron(III) palmitate, iron(II) stearate, iron(III) stearate, iron(II) oleate, iron(III) oleate, iron(II) naphthenate, iron(III) naphthenate, iron(II) neodecanoate, and iron(III) neodecanoate.

[0050] The content of the metal-organic compound is preferably 0.01 to 20% by weight, more preferably 1 to 20% by weight, even more preferably 5 to 20% by weight, and particularly preferably 10 to 20% by weight, based on the total weight of the polyether polyol and the polyisocyanate, from the viewpoint of dispersibility and adhesion. The content of the metal-organic compound is preferably 0.00001 to 10% by weight, more preferably 0.0001 to 10% by weight, even more preferably 0.001 to 8% by weight, and particularly preferably 0.01 to 6% by weight, based on the total weight of the curable composition, from the viewpoint of dispersibility and adhesion.

[0051] The curable composition of the present invention contains an inorganic filler. Preferred inorganic fillers include thermally conductive inorganic fillers (such as boron nitride, aluminum nitride, aluminum oxide, silica, magnesium oxide, and aluminum hydroxide). By using these inorganic fillers, the cured product of the curable composition can be made suitable for use as a heat dissipation member. The inorganic filler may be used alone or in combination of two or more types.

[0052] In the curable composition of the present invention, inorganic fillers other than the thermally conductive inorganic filler described above can be used as the inorganic filler, and by changing the type of inorganic filler, cured products having various functions can be obtained depending on the type of inorganic filler. For example, by including carbon or metal as a filler, a highly conductive cured product can be obtained; by including metal oxides and / or metal hydroxides, a highly insulating cured product can be obtained; by including polyimide or polyethylene, a low dielectric cured product can be obtained; by including barium titanate and / or titanium lead zirconate, a highly dielectric cured product can be obtained; by including ammonium polyphosphate and / or halogens, a highly flame-retardant cured product can be obtained; by including titanium black, a highly light-shielding cured product can be obtained; by including titanium oxide and / or zirconium oxide, a highly refractive cured product can be obtained; by including glass fibers, carbon fibers and aromatic polyamide fibers (aramid fibers), a highly strong cured product can be obtained; by including silver salts, copper salts and zinc salts, a highly antibacterial cured product can be obtained; and by including microballoons, a highly lightweight cured product can be obtained.

[0053] There are no particular restrictions on the shape of the inorganic filler contained in the curable composition of the present invention, and fibrous and particulate forms are preferably used. When particulate, spherical, plate-shaped, needle-shaped, or irregularly shaped (obtained by crushing, etc.) particles can be used. From the viewpoint of excellent moldability, spherical particles are preferred as the shape of the filler.

[0054] When the inorganic filler is composed of spherical particles, the volume-average particle diameter of the inorganic filler [D50: the particle diameter at which the cumulative particle amount in the volume-based particle size distribution reaches 50%] is preferably 0.01 to 200 μm, and more preferably 0.1 to 150 μm, from the viewpoint of excellent moldability. The volume-average particle diameter of the inorganic filler can be measured using a laser diffraction particle size distribution analyzer [e.g., SALD-2000A manufactured by Shimadzu Corporation, LA-920 manufactured by Horiba, Ltd.]. If components other than the inorganic filler are dissolved in the solvent, the solution of the composition may be measured.

[0055] In the curable composition of the present invention, the content of the inorganic filler is preferably 60 to 87% by weight, more preferably 70 to 87% by weight, and most preferably 80 to 87% by weight, based on the total weight of the curable composition, from the viewpoint of the physical properties (e.g., thermal conductivity) and moldability of the cured product of the curable composition.

[0056] The curable composition of the present invention preferably contains compound (A) represented by the following general formula (1). The inclusion of compound (A) results in excellent dispersibility of the filler, no aggregation of inorganic fillers in the curable composition, a uniform curable composition, and furthermore, inhibition of the urethane reaction by the dispersant is suppressed, resulting in excellent strength when cured.

[0057] [ka]

[0058] [In general formula (1), R 1 A is a hydrogen atom, an alkyl group having 2 to 18 carbon atoms, or an alkenyl group having 2 to 18 carbon atoms. 1 O is an alkylene oxy group with 2 to 3 carbon atoms, n1 is a number from 0 to 15, and R 2 is a hydrogen atom or -(A 2 O) n2 R 3 (R 3 A is an alkyl group having 2 to 18 carbon atoms, or an alkenyl group having 2 to 18 carbon atoms. 2 O is an alkylene oxy group with 2 to 3 carbon atoms, and n2 is a number from 0 to 15.

[0059] In general formula (1), R 1 This is a hydrogen atom, a C2-C18 alkyl group, or a C2-C18 alkenyl group. Some of the hydrogen atoms in the C2-C18 alkyl group or C2-C18 alkenyl group may be substituted with halogen atoms. Examples of alkyl groups having 2 to 18 carbon atoms include ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group, nonyl group, decyl group, undecyl group, dodecyl group, tridecyl group, tetradecyl group, pentadecyl group, hexadecyl group, heptadecyl group, and octadecyl group, each of which may be linear or branched. Examples of alkenyl groups having 2 to 18 carbon atoms include ethenyl, propenyl, butenyl, pentenyl, hexenyl, heptenyl, octenyl, nonenyl, decenyl, undecenyl, dodecenyl, tridecenyl, tetradecenyl, pentadecenyl, hexadecenyl, heptadecenyl, and octadecenyl groups. These groups may be linear or branched, and the position of the double bond is not limited. As the halogen atom, a fluorine atom is preferred. R 1 The alkyl group may be linear or branched, but linear is preferred. Furthermore, from the viewpoint of the strength of the cured product of the curable composition and the dispersibility of the filler, alkyl groups having 12 to 18 carbon atoms are preferred.

[0060] In general formula (1), A 1 O represents an alkylene oxy group having 2 to 3 carbon atoms, including ethylene oxy groups and propylene oxy groups. Of these, the ethylene oxy group is preferred from the viewpoint of the dispersibility of the filler. n1 is a number from 0 to 15, and is preferably 0 to 13, more preferably 4 to 11, from the viewpoint of good dispersibility of the filler and strength of the cured product.

[0061] R 2 is a hydrogen atom or -(A 2 O) n2 R 3 (R 3 A is an alkyl group having 2 to 18 carbon atoms, or an alkenyl group having 2 to 18 carbon atoms. 2 O is an alkylene oxy group with 2 to 3 carbon atoms, and n2 is a number from 0 to 15. R 3 For example, R 1Similar examples can be given, and the same applies to desirable items. A 2 As for O, A 1 Similar items to those listed for O can be cited, and the same applies to preferred items. The preferred range for n2 is the same as for n1. R 2 If is a hydrogen atom, then compound (A) of general formula (1) is a phosphate monoester, and R 2 ga-(A 2 O) n2 R 3 Therefore, compound (A) of general formula (1) is a phosphate diester. Also, R 2 ga-(A 2 O) n2 R 3 In the case of R 1 and R 3 n1 and n2 may be the same or different, and they may be the same or different.

[0062] As compound (A) represented by general formula (1), R 1 You may use a mixture of two or more different types, or a phosphate monoester (R 2 (a hydrogen atom) and phosphate diester (R 2 ga-(A 2 O) n2 R 3 A mixture of ) may be used. Compound (A) represented by general formula (1) is generally obtained as a mixture of phosphate monoester and phosphate diester (mono-di mixture). Salts of compound (A) represented by general formula (1) (metal salts such as sodium salt, potassium salt, and magnesium salt, ammonium salt, etc.) may also be used.

[0063] Preferred compounds (A) represented by general formula (1) include alkyl ether phosphates, alkenyl ether phosphates, alkenyl ether alkyl ether phosphates, alkyl phosphates, alkenyl phosphates, alkyl fluoride ether phosphates, and alkyl fluoride phosphates, with alkyl ether phosphates being more preferred. Compound (A) represented by general formula (1) can be obtained by phosphate esterification with a polyether and phosphorus oxidized. Compound (A) represented by general formula (1) is Disparon DA-375 [manufactured by Kusumoto Chemical Co., Ltd.], Prysurf A208N [manufactured by Daiichi Kogyo Seiyaku Co., Ltd.], Phosphanol RL-210 [manufactured by Toho Chemical Industry Co., Ltd., R 1 ,R 3 :-C 18 H 37 , A 1 O,A 2 O: Ethylene oxy group, n1, n2: 2, mono-di mixture], Phosphanol RS-710 [Manufactured by Toho Chemical Industry Co., Ltd., (C12~15) Pareth-9 phosphate, R 1 ,R 3 : C12-C15 alkyl groups, A 1 O,A 2 O: Ethylene oxy group, n1, n2: 9, mono-di mixture], Phosphanol RS-410 [Manufactured by Toho Chemical Industry Co., Ltd., (C12~15) Pareth-3 phosphate, R 1 ,R 3 : C12-C15 alkyl groups, A 1 O,A 2 O: ethylene oxy group, n1, n2: 3, mono-di mixture], phosphanol RB-410 [manufactured by Toho Chemical Industry Co., Ltd., oleth-4 phosphate, R 1 ,R 3 : C18 alkenyl group, A 1 O,A 2 O: ethylene oxy group, n1, n2: 4, mono-di mixture], phosphanol RL-310 [manufactured by Toho Chemical Industry Co., Ltd., steareth-3 phosphate, R 1 ,R 3 : C18 alkyl group, A 1 O,A 2 It can be obtained from the market as follows: O: ethylene oxy group, n1,n2:3, mono-di mixture; JP-518-O [manufactured by Johoku Chemical Industry Co., Ltd., oleyl acid phosphate, n1,n2:0, mono-di mixture]; JP-506H [manufactured by Johoku Chemical Industry Co., Ltd., butoxyethyl acid phosphate, n1,n2:1, mono-di mixture], etc.

[0064] In the curable composition of the present invention, if compound (A) is included, the content of compound (A) is preferably 0.03 to 0.9 parts by weight, more preferably 0.03 to 0.8 parts by weight, and even more preferably 0.03 to 0.6 parts by weight per 100 parts by weight of the filler. When the content of compound (A) is 0.03 parts by weight or more per 100 parts by weight of the filler, the dispersibility of the filler is excellent, there is no aggregation of the filler in the curable composition, and a uniform curable composition is obtained. When the content is 0.9 parts by weight or less, the inhibition of the urethane reaction by the dispersant is suppressed, the curability at room temperature is good, and the strength of the cured product is excellent.

[0065] The curable composition of the present invention may contain other components in addition to the polyether polyol, polyisocyanate, metal-organic compound, filler, and compound (A). Other components include polyols other than the polyether polyol mentioned above, urethane catalysts, antioxidants, dehydrating agents, colorants, surfactants, plasticizers, solvents, and ultraviolet absorbers.

[0066] Examples of urethane catalysts include amine catalysts [triethylenediamine, N-ethylmorpholine, diethylethanolamine, and 1,8-diazabicyclo(5,4,0)undecene-7, etc.] and metal catalysts [bismastris(2-ethylhexanoate), stannous octoate, dibutyltin dilaurate, and lead octoate, etc.]. Urethane catalysts can be obtained from the market as bismuth catalysts [Nitto Chemical Industries, Ltd., Neostan U-600, etc.].

[0067] When the curable composition of the present invention contains a urethane catalyst, the content of the urethane catalyst is preferably 10 parts by weight or less, more preferably 0.01 to 8 parts by weight, and particularly preferably 0.3 to 8 parts by weight, based on 100 parts by weight of the total content of polyether polyol and polyisocyanate.

[0068] Examples of antioxidants include hindered phenol antioxidants [Irganox 1135, Irganox 1010, and Irganox 1076 (all manufactured by BASF Japan)] and hindered amine antioxidants [ADEKA LA series (ADEKA Corporation)].

[0069] When the curable composition of the present invention contains an antioxidant, the amount of the antioxidant is preferably 0.5 to 10.0 parts by weight, more preferably 2.0 to 8.0 parts by weight, and particularly preferably 4.0 to 6.0 parts by weight, per 100 parts by weight of the total of the polyether polyol and polyisocyanate in the curable composition.

[0070] Examples of dehydrating agents include zeolites. When the curable composition of the present invention contains a dehydrating agent, the content of the dehydrating agent is preferably 1 to 10% by weight, more preferably 2 to 7% by weight, and particularly preferably 3 to 5% by weight, based on the total weight of the curable composition.

[0071] Anionic surfactants and cationic surfactants can be preferably used as surfactants.

[0072] Examples of anionic surfactants include carboxylate salts, sulfate esters, and sulfonates. Examples of carboxylate salts include alkali metal salts of the above fatty acids having 4 to 30 carbon atoms and alkali metal salts of polyoxyalkylene alkyl ether carboxylic acids. Examples of sulfate esters include alkali metal sulfate esters of the above aliphatic alcohols having 4 to 30 carbon atoms or AO adducts of aliphatic alcohols. Examples of sulfonates include alkali metal sulfonates of alkylphenols. Anionic surfactants can be obtained from the market as polyether carboxylic acids [Kao Corporation, Kao Akipo RLM-100], etc.

[0073] Cationic surfactants include primary to tertiary amine salts and quaternary ammonium salts. Primary to tertiary amine salts include hydrochlorides of aliphatic amines with 4 to 30 carbon atoms [primary (e.g., laurylamine), secondary (e.g., dibutylamine), and tertiary (e.g., dimethylstearylamine)], and inorganic acid (e.g., hydrochloric acid, sulfuric acid, nitric acid, and phosphoric acid) salts of monoesters of triethanolamine and fatty acids with 4 to 30 carbon atoms. Quaternary ammonium salts include inorganic acid salts of quaternary ammonium compounds with 4 to 30 carbon atoms (e.g., butyltrimethylammonium, diethyllaurylmethylammonium, dimethyldistearylammonium). Cationic surfactants can be obtained from the market as Nopcospers 092 [manufactured by Sunopco Co., Ltd., cationic surfactant], etc.

[0074] If the curable composition of the present invention contains a surfactant, the surfactant content is preferably 0.001 to 30% by weight, more preferably 0.01 to 10% by weight, and particularly preferably 0.1 to 5% by weight, based on the total weight of the curable composition.

[0075] Examples of plasticizers include phthalate-based plasticizers [diisononyl phthalate, di-(2-ethylhexyl) phthalate, diisodecyl phthalate, butyl benzyl phthalate, etc.], fatty acid ester-based plasticizers [di-(2-ethylhexyl) adipate, di-n-decyl adipate, di-(2-ethylhexyl) azelate, dibutyl sebacate, di-(2-ethylhexyl) sebacate, etc.], benzoic acid-based plasticizers [polyethylene glycol benzoate ester], epoxy-based plasticizers such as epoxidized soybean oil, trimellitate-based plasticizers, pyromelitate-based plasticizers, polyester-based plasticizers, and sulfonic acid ester-based plasticizers. Plasticizers such as diisononyl phthalate [Aekyung Petrochemical, DINP] and polyethylene glycol benzoate ester [Sanyo Chemical Industries, Ltd., EB-300] can be obtained from the market.

[0076] When the curable composition of the present invention contains a plasticizer, the amount of plasticizer is preferably 1 to 100 parts by weight, and more preferably 1 to 70 parts by weight, based on 100 parts by weight of the total amount of components other than the plasticizer contained in the curable composition.

[0077] Examples of UV absorbers include triazole-based UV absorbers [such as Tinuvin 320 (manufactured by BASF Japan)] and benzophenone-based UV absorbers [such as Cyasorb UV9 (manufactured by Cyanamide)].

[0078] The curable composition of the present invention is preferably a two-component curable composition comprising a first agent and a second agent. A two-component curable composition is a curable composition that hardens when a first component and a second component are mixed in a specific mixing ratio.

[0079] When the curable composition of the present invention is a two-component curable composition, it is preferable that the first component comprises a polyether polyol, a metal-organic compound, compound (A), and a filler, and the second component comprises a polyisocyanate, compound (A), and a filler.

[0080] The content of polyether polyol in the first component is preferably 1 to 20% by weight, and more preferably 5 to 15% by weight, based on the weight of the first component. When the content of polyether polyol in the first component is 1% by weight or more, the strength of the cured product is good, and when it is 20% by weight or less, the handling properties of the curable composition are good.

[0081] The polyisocyanate content in the second agent is preferably 1 to 20% by weight, and more preferably 10 to 18% by weight, based on the weight of the second agent. When the polyisocyanate content in the second agent is 1% by weight or more, the strength of the cured product is good, and when it is 20% by weight or less, the handling properties of the curable composition are good.

[0082] The content of the metal-organic compound in the first agent is preferably 0.01 to 20% by weight, more preferably 1 to 20% by weight, even more preferably 5 to 20% by weight, and particularly preferably 10 to 20% by weight, based on the total weight of the polyether polyol and polyisocyanate in the curable composition. When the content of the metal-organic compound in the first agent is 0.01% by weight or more, the adhesive strength and dispersibility of the filler are excellent, there is no aggregation of the filler in the first agent, and the first agent becomes uniform. When the content is 20% by weight or less, when mixed with the second agent to form a curable composition, the inhibition of the urethane reaction is suppressed, the curability at room temperature is good, and the strength of the cured product is excellent.

[0083] The content of compound (A) in the first agent is preferably 0.03 to 0.9 parts by weight, more preferably 0.05 to 0.8 parts by weight, and even more preferably 0.1 to 0.7 parts by weight, per 100 parts by weight of the filler in the first agent. When the content of compound (A) in the first agent is 0.03 parts by weight or more per 100 parts by weight of the filler in the first agent, the dispersibility of the filler is excellent, there is no aggregation of the filler in the first agent, and a uniform first agent is obtained. When it is 0.9 parts by weight or less, when mixed with the second agent to form a curable composition, inhibition of the urethane reaction is suppressed, the curability at room temperature is good, and the strength of the cured product is excellent.

[0084] The content of compound (A) in the second agent is preferably 0.03 to 0.9 parts by weight, more preferably 0.03 to 0.8 parts by weight, and even more preferably 0.05 to 0.7 parts by weight, per 100 parts by weight of filler in the second agent. When the content of compound (A) in the second agent is 0.03 parts by weight or more per 100 parts by weight of filler in the second agent, the dispersibility of the filler is excellent, there is no aggregation of the filler in the second agent, and a uniform second agent is obtained. When it is 0.9 parts by weight or less, when mixed with the first agent to form a curable composition, inhibition of the urethane reaction is suppressed, the curability at room temperature is good, and the tensile strength of the cured product is excellent.

[0085] The filler content in the first component is preferably 75 to 95% by weight, and more preferably 80 to 90% by weight, based on the weight of the first component. When the filler content in the first component is 75% by weight or more, the physical properties (e.g., thermal conductivity) of the cured product of the curable composition are good, and when it is 95% by weight or less, the handling properties of the curable composition are good.

[0086] The filler content in the second component is preferably 75 to 95% by weight, and more preferably 75 to 85% by weight, based on the weight of the second component. When the filler content in the second component is 75% by weight or more, the physical properties (e.g., thermal conductivity) of the cured product of the curable composition are good, and when it is 95% by weight or less, the handling properties of the curable composition are good.

[0087] The first agent is obtained by uniformly mixing a polyether polyol, a metal organic compound, a filler and compound (A), and other components used as needed (polyols other than polyether polyol, surfactants, plasticizers, urethane catalysts, antioxidants, dehydrating agents, etc.) using a known mixing device (such as a mixing tank with a stirring device). Each component may be mixed together, or any two or more components may be mixed beforehand, and then the remaining components (the remaining components may be a mixture) may be mixed.

[0088] The second agent is obtained by uniformly mixing polyisocyanate, filler, compound (A), and other components used as needed (surfactants, plasticizers, urethane catalysts, dehydrating agents, etc.) using a known mixing device (such as a mixing tank with a stirring device). Each component may be mixed together, or any two or more components may be mixed beforehand, and then the remaining components (the remaining components may be a mixture) may be mixed.

[0089] When the curable composition of the present invention is a two-component curable composition, a cured product can be obtained by mixing the first agent and the second agent and performing a urethane reaction in a known manner on any substrate or in a mold having a shape appropriate to the purpose. The first and second components may be mixed manually or using a known mixing device (such as a container with a stirring device), or continuously using a known two-liquid mixing and supply device.

[0090] The curable composition of the present invention exhibits good handling properties and excellent dispersibility of fillers. Furthermore, by using a thermally conductive filler, a highly thermally conductive cured product suitable for heat dissipation components and the like can be obtained. In addition, since cured products with various functions can be obtained depending on the type of filler, it is useful for fuel cell separators, lithium-ion battery materials, TIMs for power devices, LED heat dissipation materials, smartphone housings, high-frequency amplifier components, and low dielectric constant and low dielectric loss tangent materials for 5G and 6G electrical and electronic equipment.

[0091] The cured product of the present invention is a cured product of the curable composition of the present invention. The cured product of the present invention can be obtained by curing the curable composition of the present invention by a known method. Since the cured product of the present invention is a cured product of the curable composition of the present invention, it has excellent strength and is preferably used as a heat dissipation member. [Examples]

[0092] The present invention will be further described below with reference to examples and comparative examples, but the present invention is not limited thereto. Unless otherwise specified, % refers to weight percent and parts refers to parts by weight.

[0093] <Examples 1-15 and Comparative Example 1> The components shown in the "Curable Composition" column of Table 1 below were mixed in the amounts (parts by weight) shown in Table 1 to prepare the first and second components of the curable composition. Next, the first and second agents were mixed for 90 seconds at 0.7 kPa and 2000 rpm using a rotating and revolving agitator "Awatori Rentaro ARV-310P" (manufactured by Shinky Co., Ltd.) to obtain the curable compositions of Examples 1 to 15 and Comparative Example 1. The curable composition was molded into a 2mm thick sheet using a press and allowed to react by standing at 40°C for 24 hours. In Examples 1-15 and Comparative Example 1, sheet-like cured products were obtained from the curable compositions. The adhesive strength and tensile strength of the obtained cured products were evaluated by the following method. The results are shown in Table 1 or Table 2.

[0094] [Table 1]

[0095] [Table 2]

[0096] The composition of the raw materials listed by product name in Tables 1 and 2 is as follows: • PTMG-250: Polytetramethylene glycol (manufactured by Mitsubishi Chemical Group Corporation, product name: PTMG-250, number average molecular weight: 250, number of hydroxyl groups: 2) • PK-1000: Polyoxypropylene glycol (manufactured by Sanyo Chemical Industries, Ltd., product name: Sannix PK-1000, number average molecular weight: 1000, number of hydroxyl groups: 2), • TLA-100: Isocyanurate compound (trimer) of hexamethylene diisocyanate (manufactured by Asahi Kasei Corporation, product name: Duranate TLA-100) • A201H: Dimer of hexamethylene diisocyanate (manufactured by Asahi Kasei Corporation, product name: Duranate A201H) • PrenAct 44: Titanium alkoxide (manufactured by Ajinomoto Fine Techno Co., Ltd.) • PrenAct 9SA: Titanium alkoxide (manufactured by Ajinomoto Fine Techno Co., Ltd.) • PrenAct 41B: Titanium alkoxide (manufactured by Ajinomoto Fine Techno Co., Ltd.) • PrenAct 38S: Titanium alkoxide (manufactured by Ajinomoto Fine Techno Co., Ltd.) • PrenAct AL-M: Alkyl acetate aluminum diisopropylate (manufactured by Ajinomoto Fine Techno Co., Ltd.) • Starfine F-10: Zinc cyanurate (manufactured by Nissan Chemical Corporation) • RS-710: Polyoxyethylene alkyl (alkyl group with 12-15 carbon atoms) ether phosphate (manufactured by Toho Chemical Industry Co., Ltd., product name: Phosphanol RS-710) • SB-93: Aluminum hydroxide (manufactured by Nippon Light Metal Co., Ltd., volume average particle size: 100 μm) • CW-310LV: Aluminum hydroxide (manufactured by Sumitomo Chemical Co., Ltd., volume average particle size: 10 μm) • C-301N: Aluminum hydroxide (manufactured by Sumitomo Chemical Co., Ltd., volume average particle size: 1.5 μm) • U-830: Tin catalyst (manufactured by Nitto Chemical Co., Ltd., product name: Neostan U-830) • Irganox 1076: Hindered phenol antioxidant (manufactured by BASF Japan) • DIC Blue: Blue coloring agent (manufactured by DIC Corporation)

[0097] <Adhesive strength> The tensile shear adhesive strength (in MPa) of the cured products obtained in Examples 1 to 15 and Comparative Example 1 was measured in accordance with JIS K 6850 (1999) under the following conditions. • Adhesion material: Aluminum plate (A6063S), 100mm long, 25mm wide, 1.5mm thick, surface cleaned with methanol and acetone. • Test specimens: overlap length 12.5±0.25mm, overlap width 25±0.25mm, thickness 2.0±0.25mm, 5 test specimens. Curing conditions: Temperature 23±2℃, relative humidity 50±5%, stand for 24 hours or more. • Condition adjustment: Temperature 23±2℃, relative humidity 50±5%, left standing for 1 hour. • Measurement device: SHIMADZU AG-100kNG AG-X / R • Test temperature: 23±2℃ • Test humidity: Relative humidity 50±5% • Tensile speed: 5 mm / min <Tensile strength> The tensile strength (in MPa) of the cured products obtained in Examples 1 to 15 and Comparative Example 1 was measured under the following conditions in accordance with JIS K 7161-2 (2014). • Measuring device: SHIMADZU AGS-500NX AGS-X • Test temperature: 23±2℃ • Test humidity: Relative humidity 50±5% • Tensile speed: 50 mm / min

[0098] The cured products obtained in Examples 1 to 15 showed higher adhesive strength and better tensile strength than the cured product obtained in Comparative Example 1. These results show that the curable composition of the present invention exhibits excellent dispersibility of fillers and superior tensile strength and adhesive strength when cured.

Claims

1. A curable composition comprising a polyether polyol, a polyisocyanate, a metal-organic compound, and an inorganic filler, wherein the metal-organic compound is at least one selected from the group consisting of titanium alkoxide, aluminum alkoxide, and zinc acylate.

2. The curable composition according to claim 1, wherein the polyether polyol is a polyoxyalkylene polyol.

3. The curable composition according to claim 1, wherein the content of the metal organic compound is 0.01 to 20% by weight based on the total weight of the polyether polyol and the polyisocyanate.

4. The curable composition according to claim 1, further comprising compound (A) represented by the following general formula (1). 【Chemistry 1】 [In general formula (1), R １ A is a hydrogen atom or an alkyl group having 2 to 18 carbon atoms, or an alkenyl group having 2 to 18 carbon atoms. １ O is an alkylene oxy group with 2 to 3 carbon atoms, n1 is a number from 0 to 15, and R ２ is a hydrogen atom or -(A ２ O) ｎ２ R ３ (R ３ A is an alkyl group having 2 to 18 carbon atoms, or an alkenyl group having 2 to 18 carbon atoms. ２ O is an alkylene oxy group with 2 to 3 carbon atoms, and n2 is a number from 0 to 15.

5. A cured product of a curable composition according to any one of claims 1 to 4.

6. A heat dissipation member comprising the cured product described in claim 5.

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