Classifications

• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
  • C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
  • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
  • C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
  • C08G59/22—Di-epoxy compounds
  • C08G59/24—Di-epoxy compounds carbocyclic
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
  • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
  • C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
  • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
  • C08G65/04—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers only
  • C08G65/06—Cyclic ethers having no atoms other than carbon and hydrogen outside the ring
  • C08G65/16—Cyclic ethers having four or more ring atoms
  • C08G65/18—Oxetanes
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
  • C08K3/00—Use of inorganic substances as compounding ingredients
  • C08K3/01—Use of inorganic substances as compounding ingredients characterized by their specific function
  • C08K3/013—Fillers, pigments or reinforcing additives
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
  • C08K3/00—Use of inorganic substances as compounding ingredients
  • C08K3/34—Silicon-containing compounds
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
  • C08K3/00—Use of inorganic substances as compounding ingredients
  • C08K3/34—Silicon-containing compounds
  • C08K3/36—Silica
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
  • C08L67/00—Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Compositions of derivatives of such polymers
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
  • C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
  • C09J11/02—Non-macromolecular additives
  • C09J11/04—Non-macromolecular additives inorganic
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
  • C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
  • C09J11/02—Non-macromolecular additives
  • C09J11/06—Non-macromolecular additives organic
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
  • C09J163/00—Adhesives based on epoxy resins; Adhesives based on derivatives of epoxy resins
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
  • C09J167/00—Adhesives based on polyesters obtained by reactions forming a carboxylic ester link in the main chain; Adhesives based on derivatives of such polymers

Definitions

• the present invention relates to a curable composition.
• curable compositions used as adhesives to fix components are required to be able to form a cured product with a low coefficient of thermal expansion in order to prevent minute misalignments.
• curable compositions as an adhesive in a location where the effects of vibration are a concern it is required to be able to form a cured product with a low modulus of elasticity in order to reduce the effects of vibration (Patent Document 1).
• the present invention was made in light of the above-mentioned circumstances, and aims to provide a curable composition that can form a cured product that has both a low coefficient of thermal expansion and a low modulus of elasticity.
• a curable composition containing an epoxy compound having two or more alicyclic epoxy groups, an inorganic filler, a polyester having a weight average molecular weight/hydroxyl group equivalent of 0.05 or more and less than 2.0, and a cationic polymerization initiator can form a cured product that has both a low coefficient of thermal expansion and a low modulus of elasticity, and thus completed the present invention.
• the present invention based on this finding is as follows.
• a curable composition comprising: [2] The curable composition according to [1] above, wherein the content of component (B) is 20 to 90 mass% based on the solid content of the curable composition. [3] The curable composition according to [1] above, wherein the content of component (B) is 30 to 85 mass% based on the solid content of the curable composition.
• the curable composition of the present invention can be used to form a cured product that has both a low coefficient of thermal expansion and a low modulus of elasticity.
• each component may be used alone or in combination of two or more types.
• the curable composition of the present invention contains, as component (A), an epoxy compound having two or more alicyclic epoxy groups (sometimes abbreviated as "alicyclic epoxy compound” in this specification).
• the alicyclic epoxy group In curing by cationic polymerization, the alicyclic epoxy group has a higher reactivity than the epoxy group contained in glycidyl ether or the like, and therefore the curable composition of the present invention has good curability.
• epoxy compounds compared with (meth)acrylates and vinyl ethers that are generally used in curable compositions, epoxy compounds have a low cure shrinkage rate, and therefore the curable composition of the present invention has low cure shrinkage and is suitable as an adhesive for precision fixing.
• alicyclic epoxy group refers to a condensed ring group consisting of an alicyclic group and an oxirane ring, in which two adjacent carbon atoms constituting the alicyclic group form an oxirane ring (epoxy group) with an oxygen atom.
• examples of the alicyclic epoxy group include an epoxycyclopentyl group and an epoxycyclohexyl group, and the epoxycyclohexyl group is preferred.
• the alicyclic epoxy compound may have an alicyclic fused alicyclic structure in which a plurality of alicyclic epoxy groups are condensed at an alicyclic moiety.
• the number of alicyclic epoxy groups in the alicyclic epoxy compound is preferably 2 to 4, and particularly preferably 2.
• Alicyclic epoxy compounds include, for example, those represented by formulas (I) to (III):
• L 1 represents a single bond or a divalent hydrocarbon group, a carbonyl group, an ether bond, an ester bond, a carbonate bond, an amide bond, or a group in which a plurality of these are linked together;
• L 2 to L 7 each independently represent a divalent hydrocarbon group, a carbonyl group, an ether bond, an ester bond, a carbonate bond, an amide bond, or a group in which a plurality of these are linked together.
• “a compound represented by formula (I)” may be abbreviated as “compound (I)”
• compounds represented by other formulae may also be abbreviated in the same manner.
• the divalent hydrocarbon group is preferably an alkylene group having 1 to 18 carbon atoms, or a divalent alicyclic hydrocarbon group having 5 to 7 carbon atoms.
• the alkylene group having 1 to 18 carbon atoms may be either linear or branched. Examples of the alkylene group having 1 to 18 carbon atoms include a methylene group, a methylmethylene group, a dimethylmethylene group, an ethylene group, a trimethylene group, and a propylene group.
• the divalent alicyclic hydrocarbon group having 5 to 7 carbon atoms is preferably a cycloalkylene group having 5 to 7 carbon atoms or a cycloalkylidene group having 5 to 7 carbon atoms.
• Examples of the cycloalkylene group having 5 to 7 carbon atoms include a 1,2-cyclopentylene group, a 1,3-cyclopentylene group, a 1,2-cyclohexylene group, a 1,3-cyclohexylene group, and a 1,4-cyclohexylene group.
• Examples of the cycloalkylidene group having 5 to 7 carbon atoms include a cyclopentylidene group and a cyclohexylidene group.
• Preferred compounds (I) include, for example, compounds represented by formulas (I-1) to (I-8):
• the compound (I-6) and the compound (I-8) may each be a mixture of compounds having different numbers of repeating units.
• n1 is preferably an integer of 1 to 6, and more preferably 1.
• the alkylene group having 1 to 8 carbon atoms in formula (I-8) may be either linear or branched. Examples of the alkylene group having 1 to 8 carbon atoms include a methylene group, a methylmethylene group, a dimethylmethylene group, an ethylene group, a trimethylene group, a propylene group, a tetramethylene group, a pentamethylene group, a hexamethylene group, and an octamethylene group.
• Preferred compound (II) is, for example, the compound represented by formula (II-1):
• n3 and n4 each independently represent an integer of 2 to 30.
• the compound (II-1) may be a mixture of compounds having different numbers of repeating units.
• Preferred compound (III) is, for example, the compound represented by formula (III-1):
• n5 to n8 each independently represent an integer of 2 to 30.
• the compound (III-1) may be a mixture of compounds having different numbers of repeating units.
• the alicyclic epoxy compound is preferably selected from compounds (I-1) to (I-8), (II-1) and (III-1).
• the alicyclic epoxy compound is more preferably selected from compounds (I-1) to (I-7).
• the alicyclic epoxy compound is further preferably selected from compounds (I-1) and (I-6).
• a commercially available alicyclic epoxy compound can be used.
• Examples of commercially available products include “Celloxide 2021P”, “Celloxide 2081”, and “Celloxide 8000” manufactured by Daicel Corporation; “Synasia S-21E”, “Synasia S-28”, and “Synasia S-60” manufactured by Synasia; and “TTA60”, “TTA2081”, and “TTA2083” manufactured by Tetrachem.
• the molecular weight of the alicyclic epoxy compound is preferably less than 1000, more preferably 900 or less, even more preferably 800 or less, even more preferably 700 or less, and particularly preferably 600 or less.
• the lower limit of the molecular weight of the alicyclic epoxy compound is not particularly limited, but from the viewpoint of suppressing outgassing, the molecular weight is preferably 100 or more, more preferably 125 or more, and even more preferably 150 or more.
• the molecular weight of the alicyclic epoxy compound means the weight average molecular weight (sometimes abbreviated as "Mw" in this specification). This Mw can be calculated, for example, in terms of polystyrene by gel permeation chromatography (GPC).
• the viscosity (25°C) of the alicyclic epoxy compound is preferably 10 to 3000 mPa ⁇ s, and more preferably 25 to 2000 mPa ⁇ s, from the viewpoint of the fluidity of the curable composition at room temperature.
• viscosity (25°C) means the viscosity at 25°C measured using a vibration viscometer.
• the epoxy equivalent of an alicyclic epoxy compound is preferably 50 to 500 g/eq, more preferably 75 to 450 g/eq, and even more preferably 90 to 400 g/eq.
• the "epoxy equivalent" of an epoxy compound means the number of grams of an epoxy compound containing 1 gram equivalent of epoxy groups. This epoxy equivalent value can be determined according to the method specified in JIS K 7236. Theoretically, the epoxy equivalent can be calculated by dividing the molecular weight of an epoxy compound by the number of epoxy groups that the compound has.
• the content of component (A) is preferably 10 parts by mass or more, more preferably 20 parts by mass or more, and even more preferably 25 parts by mass or more, per 100 parts by mass of the total solid content of the components other than component (B) (i.e., inorganic filler) of the curable composition.
• component (D) is added to the curable composition, the content of component (A) is preferably 80 parts by mass or less, more preferably 75 parts by mass or less, and even more preferably 65 parts by mass or less, per 100 parts by mass of the total solid content of the components other than component (B) of the curable composition.
• the content of component (A) is preferably 3 mass% or more, more preferably 5 mass% or more, and even more preferably 7 mass% or more, based on the solid content of the curable composition. Also, from the viewpoint of balance with the content of component (B) (i.e., inorganic filler), the content of component (A) is preferably 70 mass% or less, more preferably 60 mass% or less, and even more preferably 50 mass% or less, based on the solid content of the curable composition.
• the curable composition of the present invention does not contain any epoxy compounds other than component (A) (e.g., bisphenol A type epoxy resin) or contains epoxy compounds other than component (A) in a content of 60 mass% or less based on the total of epoxy compounds other than component (A) and component (A) (i.e., limit the content of epoxy compounds other than component (A) to 60 mass% or less based on the total of epoxy compounds other than component (A) and component (A)).
• the content of epoxy compounds other than component (A) is more preferably 50 mass% or less, and even more preferably 40 mass% or less based on the total of epoxy compounds other than component (A) and component (A). It is particularly preferable that the curable composition of the present invention does not contain any epoxy compounds other than component (A).
• epoxy compound means a compound having an epoxy group.
• the curable composition of the present invention comprises an inorganic filler as component (B).
• component (B) contributes to a low coefficient of thermal expansion of the cured product.
• component (C) contributes to a synergistic effect that allows the coefficient of thermal expansion of the cured product to be significantly reduced in the present invention. This presumed mechanism will be explained below, but the present invention is not limited to this presumed mechanism.
• the present invention is characterized by using component (C) (a polyester having a weight average molecular weight/hydroxyl equivalent of 0.05 or more and less than 2.0) in addition to component (B). It is presumed that when the curable composition of the present invention is cured, component (A) (alicyclic epoxy compound) and component (C) undergo phase separation, resulting in a sea-island structure in which component (A) is the sea and component (C) are the islands.
• component (A) portion expands due to the heat generated during curing, but when the obtained cured product is cooled, it is presumed that the component (C) portion shrinks more than the component (A) portion. Therefore, when the cured product thermally expands, the contraction of the component (C) portion offsets the expansion of the component (A) portion, and it is presumed that a low thermal expansion coefficient is achieved for the entire cured product.
• the average thermal expansion coefficient of Examples 1 to 9, which used components (B) and (C) in combination was significantly lower than that of Comparative Examples 1 and 2, which did not use components (B) or (C).
• This significant decrease in the average thermal expansion coefficient is presumed to be due to the synergistic effect of using components (B) and (C) in combination.
• This synergistic effect is presumed to be due to the fact that, by using component (B), the islands of component (C) become smaller in the sea-island structure caused by phase separation of components (A) and (C), and as a result, the effect of component (C) is evenly exerted throughout the cured product.
• inorganic fillers include silica, alumina, glass, cordierite, barium sulfate, barium carbonate, talc, clay, mica powder, zinc oxide, hydrotalcite, boehmite, aluminum hydroxide, magnesium hydroxide, calcium carbonate, magnesium carbonate, magnesium oxide, boron nitride, aluminum nitride, manganese nitride, aluminum borate, strontium carbonate, strontium titanate, calcium titanate, magnesium titanate, bismuth titanate, titanium oxide, zirconium oxide, barium titanate, barium zirconate titanate, barium zirconate, calcium zirconate, zirconium phosphate, and zirconium tungstate phosphate.
• Component (B) is preferably selected from silica and cordierite, and more preferably silica.
• silica include fused silica, fumed silica, crystalline silica, synthetic silica, hollow silica, and the like. From the viewpoint of preventing silica from settling, the silica is preferably a mixture of fused silica and fumed silica. When a mixture of fused silica and fumed silica is used, the mass ratio of fused silica:fumed silica is preferably 10:1 to 200:1, and more preferably 20:1 to 100:1.
• the particle diameter of the inorganic filler is preferably 20 ⁇ m or less, more preferably 15 ⁇ m or less, and even more preferably 10 ⁇ m or less, from the viewpoint of reducing the practical adhesive thickness and reducing misalignment due to thermal expansion, etc.
• the particle diameter of the inorganic filler is preferably 5 nm or more, more preferably 7 nm or more, and even more preferably 10 nm or more.
• the "particle size" of an inorganic filler means a median size that can be calculated by a laser diffraction/scattering method based on Mie scattering theory.
• a particle size distribution of an inorganic filler can be created on a volume basis using a laser diffraction/scattering particle size distribution measuring device, and the median size can be calculated. More specifically, a measurement sample is prepared by weighing 100 mg of inorganic filler and 10 g of dispersion medium into a vial and dispersing the sample with sound waves for 10 minutes.
• a laser diffraction particle size distribution measuring device is used to measure the volume-based particle size distribution of the inorganic filler using a flow cell method with blue and red light source wavelengths, and the median size can be calculated from the particle size distribution obtained.
• An example of a laser diffraction particle size distribution measuring device is the "LA-960" manufactured by Horiba, Ltd.
• the specific surface area of the inorganic filler is preferably 0.1 m 2 /g or more, more preferably 0.5 m 2 /g or more, and even more preferably 1 m 2 /g or more, from the viewpoint of reducing the practical adhesive thickness and reducing positional deviation due to thermal expansion, etc.
• the upper limit of the specific surface area of the inorganic filler is not particularly limited, but is preferably 300 m 2 /g or less, more preferably 250 m 2 /g or less, and even more preferably 200 m 2 /g or less.
• the specific surface area of the inorganic filler can be obtained by adsorbing nitrogen gas to the sample surface using a specific surface area measuring device (Macsorb HM-1210 manufactured by Mountech Co., Ltd.) according to the BET method, and using the BET multipoint method.
• a specific surface area measuring device Macsorb HM-1210 manufactured by Mountech Co., Ltd.
• the inorganic filler may be surface-treated with an appropriate surface treatment agent.
• an appropriate surface treatment agent such as vinyl-based silane coupling agents such as vinyltrimethoxysilane and vinyltriethoxysilane; epoxy-based silane coupling agents such as 2-(3,4-epoxycyclohexyl)ethyltrimethoxysilane, 3-glycidoxypropylmethyldimethoxysilane, 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropylmethyldiethoxysilane, 3-glycidoxypropyltriethoxysilane, and 8-glycidoxyoctyltrimethoxysilane; styryl-based silane coupling agents such as p-styryltrimethoxysilane; 3-methacryloxypropylmethyldimethoxysilane, 3-methacryloxypropyltrieth
• amino-based silane coupling agents such as N-phenyl-8-aminooctyltrimethoxysilane, N-(vinylbenzyl)-2-aminoethyl-3-aminopropyltrimethoxysilane; isocyanurate-based silane coupling agents such as tris-(trimethoxysilylpropyl)isocyanurate; ureido-based silane coupling agents such as 3-ureidopropyltrialkoxysilane; mercapto-based silane coupling agents such as 3-mercaptopropylmethyldimethoxysilane and 3-mercaptopropyltrimethoxysilane; isocyanate-based silane coupling agents such as 3-isocyanatepropyltriethoxysilane;
• the surface treatment agent include acid anhydride-based silane coupling agents such as silylpropylsuccinic anhydride; and non-silane coupling alkoxysilane
• surface treatment agents include, for example, Shin-Etsu Chemical Co., Ltd.'s "KBM-1003” and “KBE-1003” (vinyl silane coupling agents); "KBM-303", “KBM-402”, “KBM-403”, “KBM-4803", “KBE-402”, and “KBE-403” (epoxy silane coupling agents); and "KBM-1403” (styryl silane coupling agents).
• the degree of surface treatment with the surface treatment agent is preferably within a specified range from the viewpoint of improving the dispersibility of the inorganic filler.
• the inorganic filler is preferably surface-treated with 0.2 to 5 parts by mass of the surface treatment agent per 100 parts by mass of the inorganic filler, more preferably with 0.2 to 3 parts by mass of the surface treatment agent, and even more preferably with 0.3 to 2 parts by mass of the surface treatment agent.
• the degree of surface treatment with the surface treatment agent can be evaluated by the amount of carbon per unit surface area of the inorganic filler.
• the amount of carbon per unit surface area of the inorganic filler is preferably 0.02 mg/ m2 or more, more preferably 0.1 mg/ m2 or more, and even more preferably 0.2 mg/ m2 or more.
• the amount of carbon is preferably 1.0 mg/ m2 or less, more preferably 0.8 mg/ m2 or less, and even more preferably 0.5 mg/ m2 or less.
• the amount of carbon per unit surface area of the inorganic filler can be measured after the surface-treated inorganic filler is washed with a solvent (e.g., methyl ethyl ketone (MEK)). Specifically, a sufficient amount of MEK as a solvent is added to the inorganic filler that has been surface-treated with a surface treatment agent, and ultrasonic cleaning is performed at 25°C for 5 minutes. After removing the supernatant and drying the solids, the amount of carbon per unit surface area of the inorganic filler can be measured using a carbon analyzer.
• a carbon analyzer An example of a carbon analyzer that can be used is the EMIA-320V manufactured by Horiba, Ltd.
• the content of component (B) is preferably 30 parts by mass or more, more preferably 40 parts by mass or more, and even more preferably 50 parts by mass or more, per 100 parts by mass of the total solid content of the components other than component (B) in the curable composition. Also, from the viewpoint of a low modulus of elasticity of the cured product, the content of component (B) is preferably 600 parts by mass or less, more preferably 500 parts by mass or less, and even more preferably 400 parts by mass or less, per 100 parts by mass of the total solid content of the components other than component (B) in the curable composition.
• the content of component (B) is preferably 20% by mass or more, more preferably 30% by mass or more, and even more preferably 40% by mass or more, based on the solid content of the curable composition. Also, from the viewpoint of a low modulus of elasticity of the cured product, the content of component (B) is preferably 90% by mass or less, more preferably 85% by mass or less, and even more preferably 80% by mass or less, based on the solid content of the curable composition.
• the curable composition of the present invention contains, as component (C), a polyester having a weight average molecular weight (Mw)/hydroxyl equivalent of 0.05 or more and less than 2.0. It is presumed that the use of component (C) achieves a low coefficient of thermal expansion of the cured product through the above-mentioned mechanism.
• the Mw of component (C) can be calculated in terms of polystyrene by gel permeation chromatography (GPC).
• GPC gel permeation chromatography
• the Mw of component (C) can be calculated by GPC under the following conditions.
• Measuring device Tosoh Corporation "HLC-8420GPC”
• Data processing Tosoh Corporation "GPC Workstation EcoSEC-WorkStation”
• Developing solvent tetrahydrofuran
• Flow rate 0.35 ml/min Standard: The following monodisperse polysty
• the "hydroxyl equivalent" of a polyester means the molecular weight per hydroxyl group of the polyester (i.e., the molecular weight of the polyester/the number of hydroxyl groups possessed by the polyester), and is a dimensionless quantity without units, like the molecular weight.
• the Mw/hydroxyl equivalent of component (C) is 0.05 or more and less than 2.0, preferably 0.1 to 1.5, and more preferably 0.15 to 1.0.
• the Mw of component (C) is preferably from 300 to 30,000, more preferably from 500 to 25,000, and even more preferably from 1,000 to 20,000.
• the content of component (C) is preferably 10 parts by mass or more, more preferably 15 parts by mass or more, and even more preferably 20 parts by mass or more, per 100 parts by mass of the total solid content of the components other than component (B) (i.e., inorganic filler) of the curable composition.
• the content of component (C) is preferably 70 parts by mass or less, particularly preferably 60 parts by mass or less, and even more preferably 50 parts by mass or less, per 100 parts by mass of the total solid content of the components other than component (B) of the curable composition.
• the content of component (C) is preferably 1 mass% or more, more preferably 3 mass% or more, and even more preferably 5 mass% or more, based on the solid content of the curable composition. From the viewpoint of good curability of the curable composition, the content of component (C) is preferably 50 mass% or less, more preferably 40 mass% or less, and even more preferably 30 mass% or less, based on the solid content of the curable composition.
• Component (C) may be, for example, a polyester obtained by condensation polymerization of a dicarboxylic acid and a diol.
• dicarboxylic acids include aliphatic carboxylic acids such as adipic acid, azelaic acid, sebacic acid, and dodecanedioic acid; and aromatic carboxylic acids such as terephthalic acid and isophthalic acid.
• diols examples include linear diols such as ethylene glycol, 1,4-butanediol, 1,6-hexanediol, 1,9-nonanediol, and diethylene glycol; and branched diols such as 1,2-propylene glycol, 1,3-butylene glycol, 2-methyl-1,3-propanediol, neopentyl glycol, 3-methyl-1,5-pentanediol, 2,2-dimethyl-1,3-propanediol, 2-methyl-2-propyl-1,3-propanediol, 2-butyl-2-ethyl-1,3-propanediol, and 2-methyl-1,8-octanediol.
• the dicarboxylic acids and diols may each be used alone or in combination of two or more.
• component (C) a product produced by the above-mentioned condensation polymerization of dicarboxylic acid and diol may be used, or a product obtained from a manufacturer (e.g., DIC Corporation) may be used. Note that condensation polymerization of dicarboxylic acid and diol is well known to those skilled in the art, and can be carried out appropriately by those skilled in the art.
• the curable composition of the present invention does not contain polyesters other than component (C) (i.e., polyesters having a weight average molecular weight/hydroxyl group equivalent of 2.0 or more), or contains polyesters other than component (C) in a content of 50 mass% or less relative to the total of polyesters other than component (C) and component (C) (i.e., limiting the content of polyesters other than component (C) to 50 mass% or less relative to the total of polyesters other than component (C) and component (C)).
• polyesters other than component (C) i.e., polyesters having a weight average molecular weight/hydroxyl group equivalent of 2.0 or more
• polyesters other than component (C) in a content of 50 mass% or less relative to the total of polyesters other than component (C) and component (C) i.e., limiting the content of polyesters other than component (C) to 50 mass% or less relative to the total of polyesters other than component (C) and component (C)
• the content of polyesters other than component (C) is more preferably 40 mass% or less, and even more preferably 30 mass% or less, relative to the total of polyesters other than component (C) and component (C). It is particularly preferable that the curable composition of the present invention does not contain polyesters other than component (C).
• the present invention includes a cationic polymerization initiator as component (D).
• the curable composition In curing by cationic polymerization, the curable composition has a lower cure shrinkage rate and the obtained cured product has higher heat resistance than in curing by photoradical polymerization or thermal anionic polymerization.
• the cationic polymerization initiator of component (D) may be a photo-cationic polymerization initiator or a thermal cationic polymerization initiator, so long as it can react with the alicyclic epoxy group in the alicyclic epoxy compound of component (A) and the oxetanyl group in the oxetane compound having two or more oxetanyl groups described below to initiate a cationic polymerization reaction.
• the photocationic polymerization initiator is preferably a photoacid generator, which is an agent that generates protons or Lewis acids upon irradiation with light.
• Photoacid generators are well known to those skilled in the art, and are not particularly limited in the present invention, and any known photoacid generator can be used.
• photoacid generators include those described in WO2019/146736, such as triphenylsulfonium hexafluoroantimonate, triphenylsulfonium hexafluorophosphate, p-(phenylthio)phenyldiphenylsulfonium hexafluoroantimonate, p-(phenylthio)phenyldiphenylsulfonium hexafluorophosphate, 4-chlorophenyldiphenylsulfonium hexafluorophosphate, 4-chlorophenyldiphenylsulfonium hexafluoroantimonate, bis[4-(diphenylsulfonio)phenyl]sulfide bishexafluorophosphate, bis[4-(diphenylsulfonio)phenyl]sulfide bishexafluoroantimonate, (2,4-cyclopent
• photoacid generator examples include those described in WO2018/110297 and those described in WO2020/171186 (e.g., p-(phenylthio)phenyldiphenylsulfonium tris(pentafluoroethyl)trifluorophosphate). Further examples of the photoacid generator include other known salts containing sulfonium cations and commercially available salts containing sulfonium cations.
• the photoacid generator may be a commercially available product.
• commercially available products include “Irgacure 261", “Irgacure 290", and “CG-24-61” manufactured by BASF Corporation; "CPI-110P”, “CPI-110A”, “CPI-110B”, “CPI-210S”, “CPI-310B”, “VC-1S”, “CPI-410S”, and “CPI-410B” manufactured by San-Apro Corporation; and “Cyracure UVI-6970", “Cyracure UVI-6974", “Cyracure UVI-6990", and “Cyracure UVI-6974” manufactured by Union Carbide Corporation, USA.
• Examples include “Lacure UVI-950”; “DAICATII” manufactured by Daicel; “UVAC1591” manufactured by Daicel Allnex; “CI-2481”, “CI-2734", “CI-2823”, and “CI-2758” manufactured by Nippon Soda; "FFC509” manufactured by 3M; "BBI-102", “BBI-101", “BBI-103”, “MPI-103”, “TPS-103”, “MDS-103”, “DTS-103", “NAT-103", and “NDS-103” manufactured by Midori Chemical Co., Ltd.
• the thermal cationic polymerization initiator is preferably a thermal acid generator, which is an agent that generates protons or Lewis acids upon heating.
• Thermal acid generators are well known to those skilled in the art, and are not particularly limited in the present invention, and any known thermal acid generator can be used.
• thermal acid generator examples include organic onium salt compounds in which a cation component and an anion component are paired, as described in WO2019/146736.
• cation component examples include organic sulfonium cations, organic oxonium cations, organic ammonium cations, organic phosphonium cations, and organic iodonium cations.
• Examples of the anion component include BF 4 - , B(C 6 F 5 ) 4 - , SbF 4 - , Sb(C 6 F 5 ) 4 - , AsF 6 - , PF 6 - , PF 6 - , CF 3 SO 3 - , C 4 F 9 SO 3 - , (CF 3 SO 2 ) 3 C - , and the like.
• examples of the thermal acid generator include the thermal acid generators described in WO2018/110297. Additionally, the thermal acid generator may include other known salts containing quaternary ammonium cations or commercially available salts containing quaternary ammonium cations.
• Thermal acid generators may be commercially available. Examples of commercially available products include “K-PURE TAG-2678”, “K-PURE TAG-2681”, “K-PURE TAG-2689", “K-PURE TAG-2690", "K-PURE TAG-2700", “K-PURE CXC-1612", “K-PURE CXC-1614”, “K-PURE CXC-1615”, “K-PURE CXC-1616", and "K-PURE CXC-1617".
• Component (D) is preferably selected from a photoacid generator and a thermal acid generator.
• the photoacid generator and the thermal acid generator may be used alone or in combination of two or more.
• both a photoacid generator and a thermal acid generator may be used as component (D).
• the curable composition of the present invention can be used, for example, in applications where it is preliminarily cured by irradiation with light and then fully cured by heating.
• the content of component (D) is preferably 0.01 parts by mass or more, more preferably 0.05 parts by mass or more, and even more preferably 0.1 parts by mass or more, per 100 parts by mass of the total solid content of the components other than component (B) (i.e., inorganic filler) of the curable composition.
• the content of component (D) is preferably 20 parts by mass or less, more preferably 15 parts by mass or less, and even more preferably 10 parts by mass or less, per 100 parts by mass of the total solid content of the components other than component (B) of the curable composition.
• the content of component (D) is preferably 0.05 mass% or more, more preferably 0.3 mass% or more, and even more preferably 0.5 mass% or more, based on the solid content of the curable composition. From the viewpoint of storage stability of the curable composition, the content of component (D) is preferably 15 mass% or less, more preferably 10 mass% or less, and even more preferably 5 mass% or less, based on the solid content of the curable composition.
• the curable composition of the present invention may further contain other components in addition to the components (A) to (D) as necessary.
• the other components include an oxetane compound having two or more oxetanyl groups, a photosensitizer, etc.
• An oxetane compound having two or more oxetanyl groups contributes to low cure shrinkage of a curable composition.
• the number of oxetanyl groups in the oxetane compound is preferably 2 to 4, and more preferably 2.
• the oxetane compound may be, for example, a compound represented by formula (IV) or formula (V):
• R 1 to R 4 each independently represent a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 5 to 7 carbon atoms, an aryl group having 6 to 10 carbon atoms which may be substituted with an alkyl group having 1 to 6 carbon atoms, an aralkyl group having 6 to 16 carbon atoms, an allyl group, a furyl group, or a thienyl group;
• L9 is a polyoxyalkylene group, an alkylene group having 1 to 6 carbon atoms, a cycloalkylene group having 5 to 7 carbon atoms, an arylene group having 6 to 10 carbon atoms, a divalent group in which an alkylene group having 1 to 6 carbon atoms and an arylene group having 6 to 10 carbon atoms are linked together, or a group represented by the following formula (VI) or (VII):
• -L 10 - represents -O-, -S-, -CH 2 -, -NH-, -SO-, -SO 2 -, -C(CF 3 ) 2 - or -C(CH 3 ) 2 -; and L 11 represents an alkylene group having 1 to 6 carbon atoms, a cycloalkylene group having 5 to 7 carbon atoms or an arylene group having 6 to 10 carbon atoms. and m1 represents an integer of 1 to 3.
• the compound (V) may be a mixture of compounds having different numbers of repeating units.
• the alkyl group having 1 to 6 carbon atoms in formulas (IV) and (V) may be either linear or branched.
• Examples of the alkyl group having 1 to 6 carbon atoms include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, and a hexyl group.
• Cycloalkyl groups having 5 to 7 carbon atoms in formulas (IV) and (V) include cyclopentyl, cyclohexyl, and cycloheptyl groups.
• examples of the aryl group having 6 to 10 carbon atoms that may be substituted with an alkyl group having 1 to 6 carbon atoms include a phenyl group, a naphthyl group, a tolyl group, and a xylyl group.
• Examples of the aralkyl group having 6 to 16 carbon atoms in formulas (IV) and (V) include a benzyl group and a phenethyl group.
• the number of carbon atoms in the alkylene group in the polyoxyalkylene group in formula (V) is preferably 1 to 4.
• the number of repeating oxyalkylene groups in the polyoxyalkylene group is preferably 2 to 30.
• the alkylene group having 1 to 6 carbon atoms in formulas (VI) and (VII) may be either linear or branched.
• Examples of the alkylene group having 1 to 6 carbon atoms include a methylene group, an ethylene group, a trimethylene group, a propylene group, a tetramethylene group, a pentamethylene group, and a hexamethylene group.
• Cycloalkylene groups having 5 to 7 carbon atoms in formulas (VI) and (VII) include 1,2-cyclopentylene, 1,3-cyclopentylene, 1,2-cyclohexylene, 1,3-cyclohexylene, 1,4-cyclohexylene, 1,2-cycloheptylene, 1,3-cycloheptylene, and 1,4-cycloheptylene.
• Examples of the arylene group having 6 to 10 carbon atoms in formulas (VI) and (VII) include a benzenediyl group and a biphenyldiyl group.
• the alkylene group having 1 to 6 carbon atoms and the arylene group having 6 to 10 carbon atoms may each be one or more, and examples thereof include a benzene-4,4-diylbismethylene group (-CH 2 -Ph-CH 2 -) and a biphenyl-4,4'-diylbismethylene group (-CH 2 -Ph-Ph-CH 2 -).
• the oxetane compound is preferably selected from the compound represented by the following formula (IV-1) and the compound represented by the following formula (V-1), and is more preferably the compound represented by the following formula (IV-1).
• Compound (V-1) may be a mixture of compounds having different numbers of repeating units.
• m2 represents an integer from 1 to 3.
• oxetane compounds can be used. Examples of commercially available products include “OXT-121" and “OXT-221” manufactured by Toagosei Co., Ltd., and “OXBP” and “OXIPA” manufactured by Ube Industries, Ltd.
• the molecular weight of the oxetane compound is preferably 180 or more, more preferably 190 or more, and even more preferably 200 or more.
• the upper limit of the molecular weight of the oxetane compound is appropriately selected depending on the viscosity of the curable composition, but the molecular weight is preferably 400 or less. If the molecular weight of the oxetane compound is 180 or more, the oxetane compound is less likely to volatilize from the curable composition.
• the molecular weight of the oxetane compound means the weight average molecular weight (Mw). This Mw can be calculated, for example, in terms of polystyrene by gel permeation chromatography (GPC).
• the viscosity (25°C) of the oxetane compound is preferably 1 to 10,000 mPa ⁇ s, and more preferably 2 to 5,000 mPa ⁇ s, from the viewpoint of the fluidity of the curable composition at room temperature.
• the content is preferably 3 parts by mass or more, more preferably 5 parts by mass or more, and even more preferably 10 parts by mass or more, per 100 parts by mass of the total solid content of the components other than component (B) (i.e., inorganic filler) of the curable composition, from the viewpoint of low cure shrinkage of the curable composition.
• the content is preferably 80 parts by mass or less, more preferably 75 parts by mass or less, and even more preferably 70 parts by mass or less, per 100 parts by mass of the total solid content of the components other than component (B) of the curable composition, from the viewpoint of adhesiveness of the curable composition.
• the content is preferably 1 mass% or more, more preferably 2 mass% or more, and even more preferably 3 mass% or more, based on the solid content of the curable composition, from the viewpoint of low cure shrinkage of the curable composition. Furthermore, when an oxetane compound is used, the content is preferably 50 mass% or less, more preferably 40 mass% or less, and even more preferably 30 mass% or less, based on the solid content of the curable composition, from the viewpoint of adhesiveness of the curable composition.
• Photosensitizer When a cationic photopolymerization initiator (particularly a photoacid generator) is used as component (D), it is preferable to use a photosensitizer in order to increase the activity of the cationic photopolymerization initiator and thereby increase the curability of the curable composition.
• a photosensitizer is a compound that has an absorption band in a longer wavelength range than the absorption band of a photocationic polymerization initiator, and is excited by light absorption, and then electrons or energy are transferred, contributing to the decomposition of the photocationic polymerization initiator and the generation of polymerization initiation species.
• Photosensitizers can be mixed appropriately depending on the wavelength of the light source used for photocuring. Photosensitizers are well known to those skilled in the art, and are not particularly limited in the present invention, and any known photosensitizer can be used.
• photosensitizers include anthracene compounds such as dimethylanthracene, 9,10-diethoxyanthracene, and 9,10-dibutoxyanthracene; thioxanthone compounds such as 2-isopropylthioxanthone and diethylthioxanthone; quinone compounds such as 2-ethylanthraquinone and ( ⁇ )-camphorquinone; naphthalene compounds such as dialkoxynaphthalene; and aromatic diketone compounds such as benzil and curcumin.
• anthracene compounds such as dimethylanthracene, 9,10-diethoxyanthracene, and 9,10-dibutoxyanthracene
• thioxanthone compounds such as 2-isopropylthioxanthone and diethylthioxanthone
• quinone compounds such as 2-ethylanthraquinone and ( ⁇ )-camphorquinone
• the photosensitizer is preferably selected from the group of anthracene compounds (e.g., 9,10-dibutoxyanthracene), thioxanthone compounds, and quinone compounds that have an absorption band in the wavelength region greater than 350 nm and are prone to electron transfer with aromatic sulfonium salt-based or aromatic iodonium salt-based photocationic polymerization initiators, as these have an appropriate level of absorbance in the long wavelength region, are less likely to cause poor dispersion in the curable composition, and are also preferable from the standpoint of improving curability and curing speed during curing.
• anthracene compounds e.g., 9,10-dibutoxyanthracene
• thioxanthone compounds e.g., 9,10-dibutoxyanthracene
• quinone compounds that have an absorption band in the wavelength region greater than 350 nm and are prone to electron transfer with aromatic sulfonium salt-based or aromatic i
• the photosensitizer may be a commercially available product.
• commercially available products include "Anthracure UVS-1331", “Anthracure UVS-1101”, “Anthracure UVS-581”, and “Anthracure UVS-2171” manufactured by Air Water Performance Chemicals Inc.; and 2-isopropylthioxanthone, 2,4-diethylthioxanthone, and 2-ethylanthraquinone manufactured by Tokyo Chemical Industry Co., Ltd.
• the content is preferably 0.3 parts by mass or more, more preferably 0.5 parts by mass or more, and even more preferably 1 part by mass or more, per 100 parts by mass of the total solid content of the components other than component (B) (i.e., inorganic filler) of the curable composition, from the viewpoint of good curability of the curable composition.
• the content is preferably 20 parts by mass or less, more preferably 15 parts by mass or less, and even more preferably 10 parts by mass or less, per 100 parts by mass of the total solid content of the components other than component (B) of the curable composition, from the viewpoint of deep curability.
• a photosensitizer When a photosensitizer is used, its content is preferably 0.05 mass% or more, more preferably 0.1 mass% or more, and even more preferably 0.2 mass% or more, based on the solid content of the curable composition, from the viewpoint of good curability of the curable composition. Furthermore, when a photosensitizer is used, its content is preferably 15 mass% or less, more preferably 10 mass% or less, and even more preferably 5 mass% or less, based on the solid content of the curable composition, from the viewpoint of deep curability.
• the curable composition of the present invention can be produced by mixing components (A) to (D) and, if necessary, other components (e.g., an oxetane compound, a photosensitizer, etc.) with a known stirrer or disperser.
• a stirrer or disperser include a dissolver, a planetary mixer, a roll mill, a sand mill, a ball mill, a bead mill, a homogenizer, a high-pressure homogenizer, an agihomomomixer, and a rotation/revolution mixer.
• the curable composition of the present invention can form a cured product having both a low coefficient of thermal expansion and a low modulus of elasticity, and is therefore useful as an adhesive or sealant (particularly an adhesive for fixing precision parts).
• the curable composition of the present invention can be used to form a cured layer for an optical device that has both a low coefficient of thermal expansion and a low modulus of elasticity. Therefore, the curable composition of the present invention can be suitably used for bonding optical devices (more specifically, bonding components in optical devices). Specifically, the curable composition of the present invention can be used, for example, as an adhesive for fiber arrays and ball lenses.
• the curable composition of the present invention can be cured by light and/or heat.
• the curable composition of the present invention containing a photocationic polymerization initiator can be cured by irradiation with light of 300 mJ/cm2 or more from a mercury lamp, UV-LED, or the like.
• the curable composition of the present invention containing a thermal cationic polymerization initiator can be cured by heating at a temperature of 60 to 150°C, for example.
• Component (B): Inorganic filler 40SE-C3: Fused silica manufactured by Admatechs (particle size (median size): 3.7 ⁇ m)
• R-805 Aerosil (fumed silica) manufactured by EVONIK (particle size (median size): 12 nm)
• SS-1000 Cordierite manufactured by Marusu Yuyaku Co., Ltd. (particle diameter (median diameter): 1.7 ⁇ m)
• Polyester having a weight average molecular weight/hydroxyl group equivalent of 0.05 or more and less than 2.0 Polyester A: Polyester manufactured by DIC Corporation (weight average molecular weight: 8,500, hydroxyl equivalent: 13,000, weight average molecular weight/hydroxyl equivalent: 0.65)
• Polyester B Polyester manufactured by DIC Corporation (weight average molecular weight: 4,500, hydroxyl equivalent: 11,000, weight average molecular weight/hydroxyl equivalent: 0.41)
• FPS-120 polyester polyol manufactured by DIC Corporation (weight average molecular weight: 4,600, hydroxyl equivalent: 1,000, weight average molecular weight/hydroxyl equivalent: 4.6)
• Irgacure 290 Photoacid generator manufactured by BASF
• CPI-210S Photoacid generator manufactured by San-Apro
• CXC-1821 Thermal acid generator manufactured by King Industries
• OXT-221 oxetane compound manufactured by Toagosei Co., Ltd. (compound (IV-1), molecular weight: 214, number of oxetanyl groups in one molecule: 2, viscosity (25° C.): 12.8 mPa ⁇ s)
• UVS-1331 Photosensitizer manufactured by Air Water Performance Chemicals
• curable compositions having the blending ratios shown in the table below were prepared by the following procedure, and cured products were prepared using the obtained curable compositions.
• the obtained curable composition was applied uniformly with a glass rod onto the release-treated surface of a polyethylene terephthalate (PET) film ("NS-80A” manufactured by Toray Industries, Inc., PET film thickness: 38 ⁇ m) that had been treated with an alkyd-based release agent, and then irradiated with 365 nm ultraviolet light at 30 mW for 100 seconds to obtain a cured product with a thickness of 100 ⁇ m.
• PET polyethylene terephthalate
• Example 2 A curable composition and a cured product were produced in the same manner as in Example 1, except that the amount of "40SE-C3" manufactured by Admatechs Co., Ltd. added was changed from 300 parts to 150 parts.
• Example 3 A curable composition and a cured product were produced in the same manner as in Example 1, except that the amount of "40SE-C3" manufactured by Admatechs Co., Ltd. added was changed from 300 parts to 400 parts.
• Example 4 A curable composition and a cured product were produced in the same manner as in Example 1, except that 40 parts of "Polyester B” manufactured by DIC Corporation was used in place of 40 parts of "Polyester A” manufactured by DIC Corporation.
• Example 5 A curable composition and a cured product were produced in the same manner as in Example 1, except that the amount of "Celloxide 2021P” manufactured by Daicel Corporation was changed from 40 parts to 80 parts, and "OXT-221" manufactured by Toagosei Co., Ltd. was not used.
• Example 6 A curable composition and a cured product were produced in the same manner as in Example 1, except that 40 parts of Daicel's "Celloxide 2081" were used in place of 40 parts of Daicel's "Celloxide 2021P.”
• Example 7 A curable composition and a cured product were produced in the same manner as in Example 1, except that 10 parts of "Irgacure 290" manufactured by BASF Corporation were used instead of 10 parts of "CPI-210S” manufactured by San-Apro Ltd. and 5 parts of "UVS-1331” manufactured by Air Water Performance Chemicals Inc.
• Example 8 A curable composition and a cured product were produced in the same manner as in Example 1, except that 300 parts of "SS-1000" manufactured by Marusu Glaze Co., Ltd. was used instead of 300 parts of "40SE-C3" manufactured by Admatechs Co., Ltd., and "R-805" manufactured by EVONIK Co., Ltd. was not used.
• Example 9 A curable composition was produced in the same manner as in Example 1, except that 0.8 parts of "CXC-1821” manufactured by King Industries was used instead of 10 parts of "CPI-210S” manufactured by San-Apro Ltd. and 5 parts of "UVS-1331” manufactured by Air Water Performance Chemicals Inc. Moreover, a cured product having a thickness of 100 ⁇ m was obtained in the same manner as in Example 1, except that heat curing was carried out by heating in an oven at 120° C. for 30 minutes instead of photocuring by ultraviolet irradiation.
• Example 2 A curable composition and a cured product were produced in the same manner as in Example 1, except that "40SE-C3" manufactured by Admatechs and "R-805" manufactured by EVONIK were not used.
• Example 3 A curable composition and a cured product were produced in the same manner as in Example 1, except that 80 parts of "ZX-1059” manufactured by Nippon Steel Chemical & Material Co., Ltd. was used in place of 40 parts of "Celloxide 2021P” manufactured by Daicel Corporation and 40 parts of "OXT-221" manufactured by Toagosei Co., Ltd.
• Comparative Example 1 In Comparative Example 1, in which a polyester other than component (C) was used, the average thermal expansion coefficient of the obtained cured product was large. In Comparative Example 2, in which component (B) was not used, the average thermal expansion coefficient of the obtained cured product was large. In Comparative Example 3, in which bisphenol A type epoxy resin was used instead of component (A), the curability of the obtained curable composition was poor, and no evaluable cured product was obtained.
• the curable composition of the present invention is useful as an adhesive or sealant (particularly as an adhesive for fastening precision parts).

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