Curable compositions, heat storage materials, and articles

Abstract

The present invention provides a curable composition capable of forming a heat storage material with excellent reliability under high temperature and high humidity conditions. [Solution] A curable composition containing a compound represented by the following formula (1) and at least one polyalkylene glycol ether selected from the group consisting of polyalkylene glycol monoethers and polyalkylene glycol diethers. TIFF2026095458000016.tif33149 In formula (1), R 11 and R 12 Each of these independently represents a hydrogen atom or a methyl group, R 13 This represents a divalent group having a polyoxyalkylene chain.

Description

【Technical Field】 【0001】 The present invention relates to a curable composition, a heat storage material, and an article. 【Background Art】 【0002】 A heat storage material is a material that can extract the stored energy as heat as needed. This heat storage material is used in applications such as air conditioning equipment, floor heating equipment, refrigerators, electronic components such as IC chips, interior and exterior automotive materials, automotive parts such as canisters, and heat-insulating containers. 【0003】 As a heat storage method, latent heat type heat storage using the phase change of a substance is widely used in terms of the amount of heat. For example, Patent Document 1 discloses a heat storage material composition containing a polyalkylene glycol as a latent heat type heat storage component. 【Prior Art Documents】 【Patent Documents】 【0004】 【Patent Document 1】 Japanese Patent Application Laid-Open No. 2006-96898 【Summary of the Invention】 【Problems to be Solved by the Invention】 【0005】 According to the studies of the present inventors, there is room for further improvement in terms of the reliability of heat storage materials containing polyalkylene glycol in a high-temperature and high-humidity environment. Therefore, an object of the present invention is to provide, on one aspect, a curable composition capable of forming a heat storage material having excellent reliability in a high-temperature and high-humidity environment. 【Means for Solving the Problems】 【0006】 As a result of intensive studies, the inventors of the present invention have found that by using in combination a specific compound having a polyoxyalkylene chain and two (meth)acryloyl groups and a compound obtained by etherifying a hydroxyl group at at least one terminal of a polyalkylene glycol, it is possible to form a heat storage material having excellent reliability in a high-temperature and high-humidity environment, and have completed the present invention. The present invention provides the following [1] to [8] in some aspects. 【0007】 [1] A curable composition containing a compound represented by the following formula (1) and at least one polyalkylene glycol ether selected from the group consisting of polyalkylene glycol monoethers and polyalkylene glycol diethers. [Chemical formula] In formula (1), R 11 and R 12 each independently represent a hydrogen atom or a methyl group, and R 13 represents a divalent group having a polyoxyalkylene chain. [2] The curable composition according to [1], containing a compound represented by formula (1) having a weight-average molecular weight of 1000 or more. [3] The curable composition according to [1] or [2], containing a polyalkylene glycol ether having a weight-average molecular weight of 400 or more as the polyalkylene glycol ether. [4] The curable composition according to any one of [1] to [3], containing a polyalkylene glycol ether having a weight-average molecular weight of 5000 or less as the polyalkylene glycol ether. [5] The curable composition according to any one of [1] to [4], further containing a compound represented by the following formula (3). [Chemical formula] In formula (3), R 31 represents a hydrogen atom or a methyl group, and R 32This represents a monovalent group having a polyoxyalkylene chain. [6] A curable composition according to any one of [1] to [5], used for forming a heat storage material. [7] A heat storage material comprising a cured product of any of the curable compositions described in [1] to [6]. [8] An article comprising a heat source and a cured product of any of [1] to [6] provided to be in thermal contact with the heat source. [Effects of the Invention] 【0008】 According to one aspect of the present invention, it is possible to provide a curable composition capable of forming a heat storage material that is highly reliable in high-temperature and high-humidity environments. [Brief explanation of the drawing] 【0009】 [Figure 1] This is a schematic cross-sectional view showing one embodiment of a heat storage material. [Figure 2] This is a schematic cross-sectional view showing one embodiment of an article and a method for manufacturing the same. [Figure 3] This is a schematic cross-sectional view showing another embodiment of the article. [Figure 4] This is a schematic cross-sectional view showing another embodiment of the method for manufacturing an article. [Modes for carrying out the invention] 【0010】 The embodiments of the present invention will be described in detail below with reference to the drawings as appropriate. However, the present invention is not limited to the embodiments described below. 【0011】 In this specification, "(meth)acryloyl" means "acryloyl" and its corresponding "methacryloyl," and the same applies to similar expressions such as "(meth)acrylate" and "(meth)acrylic." 【0012】 The weight-average molecular weight (Mw) in this specification is measured under the following conditions using gel permeation chromatography (GPC) and means a value determined using polystyrene as a standard substance. · Measuring instrument: HLC-8320GPC (product name, manufactured by Tosoh Corporation) · Analytical column: TSKgel SuperMultipore HZ-H (connected in three) (product name, manufactured by Tosoh Corporation) · Guard column: TSKguardcolumn SuperMP(HZ)-H (product name, manufactured by Tosoh Corporation) · Eluent: THF · Measuring temperature: 25 °C 【0013】 [Curable composition] The curable composition according to one embodiment contains a compound represented by the following formula (1) and at least one polyalkylene glycol ether selected from the group consisting of polyalkylene glycol monoethers and polyalkylene glycol diethers. [Chemical formula] In formula (1), R 11 and R 12 each independently represent a hydrogen atom or a methyl group, and R 13 represents a divalent group having a polyoxyalkylene chain. 【0014】 In one embodiment, one of R 11 and R 12 may be a hydrogen atom and the other may be a methyl group. In another embodiment, both of R 11 and R 12 may be hydrogen atoms. In another embodiment, both of R 11 and R 12 may be methyl groups. 【0015】 The polyoxyalkylene chain is represented by, for example, the following formula (1-1). [Chemical formula] In formula (1-1), R 14 represents an alkylene group, m represents an integer greater than or equal to 2, and * represents a bond. 【0016】 R 14 The alkylene group represented by may be linear or branched. 14 R may be, for example, an alkylene group having 2 to 4 carbon atoms. Multiple R groups may be present in the polyoxyalkylene chain. 14 These may be identical to each other or different to each other. Multiple Rs present in a polyoxyalkylene chain. 14 Preferably, it is one or more selected from the group consisting of ethylene groups, propylene groups, and butylene groups, more preferably one or two selected from the group consisting of ethylene groups and propylene groups, and even more preferably all are ethylene groups. 【0017】 m may be an integer of 10 or more, or 20 or more, and may be an integer of 300 or less, 250 or less, or 200 or less. m may be an integer such that the molecular weight of the compound represented by formula (1) is, for example, 1000 or more, and from the viewpoint of obtaining a heat storage material with even better reliability in high temperature and high humidity environments, it is preferably an integer such that the molecular weight of the compound represented by formula (1) is 2000 or more, 3000 or more, 4000 or more, 5000 or more, 6000 or more, or 7000 or more. From the viewpoint of suppressing the decrease in heat storage characteristics due to supercooling, m is preferably an integer such that the molecular weight of the compound represented by formula (1) is 12000 or less, 11000 or less, 10000 or less, 9000 or less, 8000 or less, 7000 or less, 6000 or less, 5000 or less, or 4000 or less, 3000 or less, or 2000 or less. 【0018】 R 13The polyoxyalkylene chain may also be a divalent group having other organic groups in addition to the polyoxyalkylene chain. The other organic groups may be chain-like groups other than the polyoxyalkylene chain, such as a methylene chain (a chain with -CH2- as a structural unit), a polyester chain (a chain containing -COO- as a structural unit), a polyurethane chain (a chain containing -OCON- as a structural unit), etc. 【0019】 The compound represented by formula (1) is preferably the compound represented by the following formula (1-2). [ka] In formula (1-2), R 11 and R 12 R in equation (1) 11 and R 12 These are synonymous, and R 14 And m is R in equation (1-1) 14 These are synonymous with m, respectively. 【0020】 The weight-average molecular weight (Mw) of the compound represented by formula (1) may be, for example, 1000 or more, and is preferably 2000 or more, 3000 or more, 4000 or more, 5000 or more, 6000 or more, or 7000 or more, from the viewpoint of obtaining a heat storage material with even better reliability in high-temperature and high-humidity environments. The weight-average molecular weight (Mw) of the compound represented by formula (1) is preferably 12000 or less, 11000 or less, 10000 or less, 9000 or less, 8000 or less, 7000 or less, 6000 or less, 5000 or less, or 4000 or less, 3000 or less, or 2000 or less, from the viewpoint of suppressing the deterioration of heat storage characteristics due to supercooling. 【0021】 The curable composition may contain one compound represented by formula (1) having the above-described Mw, or it may contain two or more compounds represented by formula (1) having different Mw values. In the latter case, when the Mw of the compounds represented by formula (1) is measured by the method described above, two or more peaks corresponding to the respective Mw values ​​of the two or more compounds represented by formula (1) are observed in the resulting molecular weight distribution. 【0022】 In one embodiment, the curable composition may preferably contain at least one compound having an Mw of 2000 or more (referred to as compound (1A)), or it may contain at least one compound (1A) and at least one compound represented by formula (1) having an Mw of less than 2000 (referred to as compound (1B)). The Mw of compound (1A) is more preferably 3000 or more, 4000 or more, 5000 or more, 6000 or more, or 7000 or more, and may be, for example, 12000 or less, 11000 or less, or 10000 or less. The Mw of compound (1B) may be, for example, 1000 or more, or 1500 or less. 【0023】 The content of the compound represented by formula (1) may be, for example, 1% by mass or more, 2% by mass or more, or 5% by mass or more, based on the total amount of the curable composition. From the viewpoint of obtaining a heat storage material with excellent flexibility of the cured product of the curable composition and even better heat storage capacity, it is preferably 10% by mass or more, 15% by mass or more, or 20% by mass or more, and more preferably 25% by mass or more, 30% by mass or more, 35% by mass or more, or 40% by mass or more. Furthermore, if the cured product of the curable composition has excellent flexibility, it can be used by bending the cured product, for example, and the cured product is even more suitable as a heat storage material applicable to a wider range of uses. The content of the compound represented by formula (1) may be, for example, 99% by mass or less, 90% by mass or less, 80% by mass or less, 70% by mass or less, 60% by mass or less, or 50% by mass or less, based on the total amount of the curable composition. If the curable composition contains two or more compounds represented by formula (1), their total amount may be within the above range. If the curable composition contains the above compound (1A) and / or the above compound (1B), the total amount of compound (1A) and compound (1B) may be within the above range, and the respective contents of compound (1A) and compound (1B) may be within the above range. 【0024】 When the curable composition further contains a compound copolymerizable with the compound represented by formula (1) in addition to the compound represented by formula (1) (details will be described later), the content of the compound represented by formula (1) may be 1 part by mass or more, 2 parts by mass or more, or 5 parts by mass or more per 100 parts by mass of the total content of the compound represented by formula (1) and the compound copolymerizable with the compound represented by formula (1) (hereinafter referred to as "total content of polymerizable components"). From the viewpoint of obtaining a heat storage material with excellent flexibility of the cured product of the curable composition and even better heat storage capacity, it is preferably 10 parts by mass or more or 15 parts by mass or more, more preferably 20 parts by mass or more, 25 parts by mass or more, 30 parts by mass or more, or 35 parts by mass or more, and even more preferably 40 parts by mass or more. The content of the compound represented by formula (1) may be, for example, 99 parts by mass or less, 90 parts by mass or less, 80 parts by mass or less, 70 parts by mass or less, 60 parts by mass or less, or 50 parts by mass or less per 100 parts by mass of the total content of polymerizable components. 【0025】 Polyalkylene glycol ethers are represented, for example, by the following formula (2). [ka] In formula (2), R 21 and R 22 Each of these independently represents a hydrogen atom or a monovalent hydrocarbon group, and R 23 represents an alkylene group, and n represents an integer greater than or equal to 2. However, R 21 and R 22 At least one of them represents a monovalent hydrocarbon group. 21 and R 22 If only one of the groups is a monovalent hydrocarbon group, then the polyalkylene glycol ether is a polyalkylene glycol monoether. 21 and R 22 When both are monovalent hydrocarbon groups, a polyalkylene glycol ether is a polyalkylene glycol diether. 【0026】 R 21 and R 22The monovalent hydrocarbon group represented by may be, for example, an alkyl group or an aryl group, and is preferably an alkyl group. The alkyl group may be linear or branched. The number of carbon atoms in the alkyl group may be, for example, 1 or more, 10 or less, 8 or less, 6 or less, 4 or less, or 2 or less. An example of an aryl group is a phenyl group. 【0027】 R 23 The alkylene group represented by may be linear or branched, but from the viewpoint of obtaining a heat storage material with even better heat storage capacity, it is preferably linear. 23 For example, R may be an alkylene group having 2 to 4 carbon atoms. Multiple R groups may exist in a single molecule. 23 These may be identical to each other, or they may be different to each other. Multiple Rs may exist within a single molecule. 23 Preferably, all of them are ethylene groups. 【0028】 In one embodiment, R 21 and R 22 The monovalent hydrocarbon group represented is an alkyl group, and R 23 It is preferable that all alkylene groups represented are ethylene groups. That is, the polyalkylene glycol ether is preferably at least one selected from the group consisting of polyethylene glycol monoalkyl ethers and polyethylene glycol dialkyl ethers. 【0029】 n may be an integer of 10 or more, or 20 or more, and may be an integer of 100 or less, 90 or less, 80 or less, 70 or less, or 60 or less. n may be an integer such that the molecular weight of the compound represented by formula (2) is 400 or more, 500 or more, 600 or more, 700 or more, 800 or more, 900 or more, or 1000 or more. From the viewpoint of further enhancing the reliability improvement effect under high temperature and high humidity environments by etherifying the terminal hydroxyl groups of polyalkylene glycol, n is preferably an integer such that the molecular weight of the compound represented by formula (2) is 5000 or less, 4000 or less, 3000 or less, or 2500 or less. 【0030】 The weight-average molecular weight (Mw) of the compound represented by formula (2) may be, for example, 500 or more, 600 or more, 700 or more, 800 or more, 900 or more, or 1000 or more. From the viewpoint of achieving a greater reliability improvement effect under high temperature and high humidity environments by etherifying the terminal hydroxyl groups of polyalkylene glycol, the weight-average molecular weight (Mw) of the compound represented by formula (2) is preferably 5000 or less, 4000 or less, 3000 or less, or 2500 or less. 【0031】 The polyalkylene glycol ether content may be, for example, 10% by mass or more based on the total amount of the curable composition, and more preferably, 15% by mass or more, 20% by mass or more, 25% by mass or more, 30% by mass or more, 35% by mass or more, or 40% by mass or more, from the viewpoint of obtaining a heat storage material with superior heat storage capacity. The polyalkylene glycol ether content may be, for example, 80% by mass or less, 70% by mass or less, 65% by mass or less, or 60% by mass or less based on the total amount of the curable composition. 【0032】 The polyalkylene glycol ether content may be 10 parts by mass or more, 20 parts by mass or more, or 30 parts by mass or more per 100 parts by mass of the total content of polymerizable components. From the viewpoint of obtaining a heat storage material with superior heat storage capacity, it is preferably 40 parts by mass or more, more preferably 50 parts by mass or more, even more preferably 60 parts by mass or more, and may be 70 parts by mass or more, 80 parts by mass or more, 90 parts by mass or more, or 100 parts by mass or more. The polyalkylene glycol content may be 500 parts by mass or less, 400 parts by mass or less, 300 parts by mass or less, 200 parts by mass or less, 150 parts by mass or less, 120 parts by mass or less, 110 parts by mass or less, or 100 parts by mass or less per 100 parts by mass of the total content of polymerizable components. 【0033】 The curable composition may further contain a polymerization initiator. The polymerization initiator is not particularly limited as long as it is a compound that can initiate polymerization of the compound represented by formula (1) and, if necessary, compounds copolymerizable with the compound represented by formula (1) (details will be described later). The polymerization initiator may be, for example, a thermal polymerization initiator that generates radicals by heat, or a photopolymerization initiator that generates radicals by light. 【0034】 If the curable composition contains a thermal polymerization initiator, a cured product of the curable composition can be obtained by applying heat to the curable composition. In this case, the curable composition may be one that is cured by heating preferably at 105°C or higher, more preferably at 110°C or higher, and even more preferably at 115°C or higher, for example, a curable composition that is cured by heating at 200°C or lower, 190°C or lower, or 180°C or lower. The heating time when heating the curable composition may be appropriately selected according to the composition of the curable composition so that the curable composition is suitably cured. 【0035】 Examples of thermal polymerization initiators include azo compounds such as azobisisobutyronitrile, azobis-4-methoxy-2,4-dimethylvaleronitrile, azobiscyclohexanone-1-carbonitride, and azodibenzoyl; and organic peroxides such as benzoyl peroxide, lauroyl peroxide, di-t-butylperoxyhexahydroterephthalate, t-butylperoxy-2-ethylhexanoate, 1,1-t-butylperoxy-3,3,5-trimethylcyclohexane, and t-butylperoxyisopropyl carbonate. These thermal polymerization initiators may be used individually or in combination of two or more. 【0036】 If the curable composition contains a photopolymerization initiator, a cured product of the curable composition can be obtained by irradiating the curable composition with light (for example, light containing at least some wavelengths between 200 and 400 nm (ultraviolet light)). The conditions for light irradiation may be appropriately set depending on the type of photopolymerization initiator. 【0037】 The photopolymerization initiator may be, for example, a benzoin ether-based photopolymerization initiator, an acetophenone-based photopolymerization initiator, an α-ketol-based photopolymerization initiator, an aromatic sulfonyl chloride-based photopolymerization initiator, a photoactive oxime-based photopolymerization initiator, a benzoin-based photopolymerization initiator, a benzyl-based photopolymerization initiator, a benzophenone-based photopolymerization initiator, a ketal-based photopolymerization initiator, a thioxanthone-based photopolymerization initiator, an acylphosphine oxide-based photopolymerization initiator, or the like. 【0038】 Examples of benzoin ether-based photopolymerization initiators include benzoin methyl ether, benzoin ethyl ether, benzoin propyl ether, benzoin isopropyl ether, benzoin isobutyl ether, 2,2-dimethoxy-1,2-diphenylethane-1-one (trade name: Omnirad651, manufactured by IGM Resins BV), and anisole methyl ether. Examples of acetophenone-based photopolymerization initiators include 1-hydroxycyclohexylphenyl ketone (trade name: Omnirad 184, manufactured by IGM Resins BV), 4-phenoxydichloroacetophenone, 4-t-butyl-dichloroacetophenone, 1-[4-(2-hydroxyethoxy)-phenyl]-2-hydroxy-2-methyl-1-propan-1-one (trade name: Omnirad 2959, manufactured by IGM Resins BV), 2-hydroxy-2-methyl-1-phenyl-propan-1-one (trade name: Omnirad 1173, manufactured by IGM Resins B.V.), and methoxyacetophenone. 【0039】 Examples of α-ketol-based photopolymerization initiators include 2-methyl-2-hydroxypropiophenone and 1-[4-(2-hydroxyethyl)-phenyl]-2-hydroxy-2-methylpropan-1-one. Examples of aromatic sulfonyl chloride-based photopolymerization initiators include 2-naphthalenesulfonyl chloride. Examples of photoactive oxime-based photopolymerization initiators include 1-phenyl-1,1-propanedione-2-(o-ethoxycarbonyl)-oxime. 【0040】 Examples of benzoin-based photopolymerization initiators include benzoin. Examples of benzyl-based photopolymerization initiators include benzyl. Examples of benzophenone-based photopolymerization initiators include benzophenone, benzoylbenzoic acid, 3,3'-dimethyl-4-methoxybenzophenone, polyvinylbenzophenone, α-hydroxycyclohexylphenyl ketone. Examples of ketal-based photopolymerization initiators include benzyldimethylketal. Examples of thioxanthone-based photopolymerization initiators include thioxanthone, 2-chlorothioxanthone, 2-methylthioxanthone, 2,4-dimethylthioxanthone, isopropylthioxanthone, 2,4-dichlorothioxanthone, 2,4-diethylthioxanthone, isopropylthioxanthone, 2,4-diisopropylthioxanthone, dodecylthioxanthone, etc. 【0041】 Examples of acylphosphine oxide-based photopolymerization initiators include bis(2,6-dimethoxybenzoyl)phenylphosphine oxide, bis(2,6-dimethoxybenzoyl)(2,4,4-trimethylpentyl)phosphine oxide, bis(2,6-dimethoxybenzoyl)-n-butylphosphine oxide, bis(2,6-dimethoxybenzoyl)-(2-methylpropan-1-yl)phosphine oxide, bis(2,6-dimethoxybenzoyl)-(1-methylpropan-1-yl)phosphine oxide, and bis(2,6-dimethoxybenzoyl)-t-butylphosphine oxide. Bis(2,6-dimethoxybenzoyl)cyclohexylphosphine oxide, bis(2,6-dimethoxybenzoyl)octylphosphine oxide, bis(2-methoxybenzoyl)(2-methylpropan-1-yl)phosphine oxide, bis(2-methoxybenzoyl)(1-methylpropan-1-yl)phosphine oxide, bis(2,6-diethoxybenzoyl)(2-methylpropan-1-yl)phosphine oxide, bis(2,6-diethoxybenzoyl)(1-methylpropan-1-yl)phosphine oxide, bis (2,6-dibutoxybenzoyl)(2-methylpropan-1-yl)phosphine oxide, bis(2,4-dimethoxybenzoyl)(2-methylpropan-1-yl)phosphine oxide, bis(2,4,6-trimethylbenzoyl)(2,4-dipentoxyphenyl)phosphine oxide, bis(2,6-dimethoxybenzoyl)benzylphosphine oxide, bis(2,6-dimethoxybenzoyl)-2-phenylpropylphosphine oxide, bis(2,6-dimethoxybenzoyl)-2-phenylethylphosphine oxide, 2,6-dimethoxy Benzoylbenzylbutylphosphine oxide, 2,6-dimethoxybenzoylbenzyloctylphosphine oxide, bis(2,4,6-trimethylbenzoyl)-2,5-diisopropylphenylphosphine oxide, bis(2,4,6-trimethylbenzoyl)-2-methylphenylphosphine oxide, bis(2,4,6-trimethylbenzoyl)-4-methylphenylphosphine oxide, bis(2,4,6-trimethylbenzoyl)-2,5-diethylphenylphosphine oxide, bis(2,4,6-trimethylbenzoyl)-2,3,5,Examples include 6-tetramethylphenylphosphine oxide, bis(2,4,6-trimethylbenzoyl)-2,4-di-n-butoxyphenylphosphine oxide, 2,4,6-trimethylbenzoyldiphenylphosphine oxide, bis(2,6-dimethoxybenzoyl)-2,4,4-trimethylpentylphosphine oxide, bis(2,4,6-trimethylbenzoyl)isobutylphosphine oxide, 2,6-dimethoxybenzoyl-2,4,6-trimethylbenzoyl-n-butylphosphine oxide, bis(2,4,6-trimethylbenzoyl)phenylphosphine oxide, bis(2,4,6-trimethylbenzoyl)-2,4-dibutoxyphenylphosphine oxide, 1,10-bis[bis(2,4,6-trimethylbenzoyl)phosphine oxide]decane, tri(2-methylbenzoyl)phosphine oxide, etc. 【0042】 The photopolymerization initiators described above may be used individually or in combination of two or more. 【0043】 From the viewpoint of ensuring favorable polymerization, the content of the polymerization initiator is preferably 0.01 parts by mass or more, more preferably 0.02 parts by mass or more, and even more preferably 0.05 parts by mass or more, per 100 parts by mass of the total content of polymerizable components. From the viewpoint of ensuring that the molecular weight of the polymer in the cured product of the curable composition is within a suitable range, suppressing decomposition products, and obtaining suitable adhesive strength when used as a heat storage material, the content of the polymerization initiator is preferably 10 parts by mass or less, more preferably 5 parts by mass or less, even more preferably 3 parts by mass or less, and particularly preferably 1 part by mass or less, per 100 parts by mass of the total content of polymerizable components. 【0044】 The curable composition may further contain a compound copolymerizable with the compound represented by formula (1). The copolymerizable compound has, for example, a group having an ethylenically unsaturated bond (ethylenically unsaturated group). Examples of ethylenically unsaturated groups include a (meth)acryloyl group, a vinyl group, an allyl group, and the like. The copolymerizable compound is preferably a compound having a (meth)acryloyl group. 【0045】 From the viewpoint of obtaining a heat storage material with even better heat storage capacity, the curable composition preferably further contains a compound represented by the following formula (3) as the copolymerizable compound. [ka] In formula (3), R 31 R represents a hydrogen atom or a methyl group. 32 This represents a monovalent group having a polyoxyalkylene chain. 【0046】 R 32 This may be a group represented by, for example, the following formula (3-1). [ka] In formula (3-1), R 33 represents an alkylene group, R 34 * represents a hydrogen atom or alkyl group, p represents an integer of 2 or more, and * represents a bond. 【0047】 R 33 The alkylene group represented by may be linear or branched, but from the viewpoint of obtaining a heat storage material with even better heat storage capacity, it is preferably linear. 33 R may be, for example, an alkylene group having 2 to 4 carbon atoms. Multiple R groups may be present in the polyoxyalkylene chain. 33 These may be identical or different from one another. The polyoxyalkylene chain preferably has one or more selected from the group consisting of oxyethylene groups, oxypropylene groups, and oxybutylene groups, more preferably has one or more selected from the group consisting of oxyethylene groups and oxypropylene groups, and even more preferably has only oxyethylene groups. 【0048】 R 34The alkyl group represented by may be linear or branched, but is preferably linear from the viewpoint of obtaining a heat storage material with even better heat storage capacity. The number of carbon atoms in the alkyl group is preferably 1 to 15, more preferably 1 to 10, and even more preferably 1 to 5. 34 This is particularly preferably a hydrogen atom or a methyl group. 【0049】 p may be, for example, an integer of 10 or more or 20 or more, and may be an integer of 80 or less, 70 or less, or 60 or less. From the viewpoint of obtaining a heat storage material with even better heat storage capacity, p is preferably an integer such that the molecular weight of the compound represented by formula (3) is 800 or more, 900 or more, or 1000 or more, and more preferably an integer such that the molecular weight of the compound represented by formula (3) is 1200 or more, 1400 or more, 1600 or more, 1800 or more, or 2000 or more. p may also be an integer such that the molecular weight of the compound represented by formula (3) is 5000 or less, 4000 or less, 3000 or less, or 2500 or less. 【0050】 The weight-average molecular weight (Mw) of the compound represented by formula (3) is preferably 800 or more, 900 or more, or 1000 or more, and more preferably 1200 or more, 1400 or more, 1600 or more, 1800 or more, or 2000 or more, from the viewpoint of obtaining a heat storage material with even better heat storage capacity. The weight-average molecular weight (Mw) of the compound represented by formula (3) may also be 5000 or less, 4000 or less, 3000 or less, or 2500 or less. 【0051】 The content of the compound represented by formula (3) may be, for example, 10 parts by mass or more, 20 parts by mass or more, or 30 parts by mass or more, per 100 parts by mass of the total content of polymerizable components. From the viewpoint of obtaining a heat storage material with even better heat storage capacity, it is preferably 40 parts by mass or more, more preferably 50 parts by mass or more, even more preferably 60 parts by mass or more, and particularly preferably 70 parts by mass or more. The content of the compound represented by formula (3) may be, for example, 98 parts by mass or less, 90 parts by mass or less, or 80 parts by mass or less, per 100 parts by mass of the total content of polymerizable components. 【0052】 When a curable composition contains a compound represented by formula (3), it is preferable that the melting point of the compound represented by formula (3) is close to the melting point of the polyalkylene glycol ether, from the viewpoint of suitably using the cured product of the curable composition as a heat storage material. The absolute value of the difference between the melting point of the compound represented by formula (3) and the melting point of the polyalkylene glycol ether is preferably 20°C or less, more preferably 15°C or less, and even more preferably 10°C or less. 【0053】 The melting points of the compound represented by formula (3) and the polyalkylene glycol ether are measured as follows: Using a differential scanning calorimetry analyzer (e.g., TA Instruments, model number Discovery DSC250), the temperature is raised to 100°C at a rate of 20°C / min, held at 100°C for 3 minutes, then cooled to -20°C at a rate of 3°C / min, held at -20°C for 3 minutes, and then raised again to 100°C at a rate of 3°C / min. 【0054】 The curable composition may further contain a compound represented by the following formula (4) as a compound copolymerizable with the compound represented by formula (1), from the viewpoint of adjusting the hardness of the cured product of the curable composition and from the viewpoint of easily dissolving the polymerization initiator in the curable composition when the polymerization initiator is a solid. [ka] In formula (4), R 41 R represents a hydrogen atom or a methyl group. 42 represents an alkyl group. 【0055】 R 42 The alkyl group represented by may be linear or branched, and is preferably linear from the viewpoint of obtaining a heat storage material with even better heat storage capacity. The number of carbon atoms in the alkyl group may be, for example, 1 to 30. The number of carbon atoms in the alkyl group may be 1 to 11, 1 to 8, 1 to 6, or 1 to 4, and may also be 12 to 30, 12 to 28, 12 to 24, 12 to 22, 12 to 18, or 12 to 14. 【0056】 The content of the compound represented by formula (4) may be, for example, 0.5 parts by mass or more, 1 part by mass or more, or 1.5 parts by mass or more, and 10 parts by mass or less, 8 parts by mass or less, or 6 parts by mass or less, based on 100 parts by mass of the total content of polymerizable components. 【0057】 The curable composition may further contain a compound represented by the following formula (5) as a compound copolymerizable with the compound represented by formula (1). [ka] In formula (5), R 51 R represents a hydrogen atom or a methyl group. 52 This represents a monovalent group that has a reactive group. 【0058】 If the curable composition further contains a compound represented by formula (5), the compound represented by formula (1) and the compound represented by formula (5) (and other compounds copolymerizable with the compound represented by formula (1)) can be polymerized, and then the reactive group contained in the compound represented by formula (5) can be reacted with a curing agent described later to further cure the curable composition. 【0059】 R 52 The reactive group represented by is a group that can react with the curing agent described later, and is, for example, at least one group selected from the group consisting of a carboxyl group, a hydroxyl group, an isocyanate group, an amino group, and an epoxy group. That is, the compound represented by formula (5) is, for example, a carboxyl group-containing compound, a hydroxyl group-containing compound, an isocyanate group-containing compound, an amino group-containing compound, or an epoxy group-containing compound. 【0060】 Examples of carboxyl group-containing compounds include (meth)acrylic acid, carboxyethyl (meth)acrylate, carboxypentyl (meth)acrylate, itaconic acid, maleic acid, fumaric acid, crotonic acid, and isocrotonic acid. 【0061】 Examples of hydroxyl group-containing compounds include hydroxyalkyl (meth)acrylates such as 2-hydroxyethyl (meth)acrylate, 3-hydroxypropyl (meth)acrylate, 4-hydroxybutyl (meth)acrylate, 6-hydroxyhexyl (meth)acrylate, 8-hydroxyoctyl (meth)acrylate, 10-hydroxydecyl (meth)acrylate, and 12-hydroxylauryl (meth)acrylate; and hydroxyalkylcycloalkane (meth)acrylates such as (4-hydroxymethylcyclohexyl)methyl (meth)acrylate. The hydroxyl group-containing compound may also be hydroxyethyl (meth)acrylamide, allyl alcohol, 2-hydroxyethyl vinyl ether, 4-hydroxybutyl vinyl ether, diethylene glycol monovinyl ether, etc. 【0062】 Examples of isocyanate group-containing compounds include 2-methacryloyloxyethyl isocyanate and 2-acryloyloxyethyl isocyanate. 【0063】 In isocyanate group-containing compounds, the isocyanate group may be blocked (protected) by a heat-removable blocking agent (protecting group). That is, an isocyanate group-containing compound may be a compound having a blocked isocyanate group represented by the following formula (5-1). [ka] In the formula, B represents a protecting group, and * represents a bond. 【0064】 The protecting group in the blocked isocyanate group may be a protecting group that can be removed (deprotected) by heating (e.g., heating to 80-160°C). In the blocked isocyanate group, a substitution reaction between the blocking agent (protecting group) and the curing agent described later may occur under deprotection conditions (e.g., heating conditions to 80-160°C). Alternatively, in the blocked isocyanate group, an isocyanate group may be generated by deprotection, and this isocyanate group may react with the curing agent described later. 【0065】 Blocking agents for blocked isocyanate groups include oxime compounds such as formaldehyde oxime, acetaldehyde oxime, acetoxime, methyl ethyl ketoxime, and cyclohexanone oxime; pyrazole compounds such as pyrazole, 3-methylpyrazole, and 3,5-dimethylpyrazole; lactam compounds such as ε-caprolactam, δ-valerolactam, γ-butyrolactam, and β-propiolactam; mercaptan compounds such as thiophenol, methylthiophenol, and ethylthiophenol; acid amide compounds such as acetic acid amide and benzamide; and imide compounds such as succinimide and maleimide. 【0066】 Examples of compounds having a blocked isocyanate group include 2-[(3,5-dimethylpyrazolyl)carbonylamino]ethyl methacrylate and 2-(0-[1'-methylpropyleneamino]carboxyamino)methacrylate. 【0067】 Examples of amino group-containing compounds include N,N-dimethylaminoethyl (meth)acrylate, N,N-diethylaminoethyl (meth)acrylate, N,N-dimethylaminopropyl (meth)acrylate, and N,N-diethylaminopropyl (meth)acrylate. 【0068】 Examples of epoxy group-containing compounds include glycidyl (meth)acrylate, α-ethyl(meth)acrylate, glycidyl α-n-propyl(meth)acrylate, glycidyl α-n-butyl(meth)acrylate, 3,4-epoxybutyl (meth)acrylate, 4,5-epoxypentyl (meth)acrylate, 6,7-epoxyheptyl (meth)acrylate, 6,7-epoxyheptyl (meth)acrylate, 3-methyl-3,4-epoxybutyl (meth)acrylate, 4-methyl-4,5-epoxypentyl (meth)acrylate, 5-methyl-5,6-epoxyhexyl (meth)acrylate, β-methylglycidyl (meth)acrylate, and α-ethyl(meth)acrylate-β-methylglycidyl. 【0069】 The content of the compound represented by formula (5) may be, for example, 0.5 parts by mass or more, 1 part by mass or more, or 1.5 parts by mass or more, and may be 10 parts by mass or less, 8 parts by mass or less, or 5 parts by mass or less, based on 100 parts by mass of the total content of polymerizable components. 【0070】 The total content of polymerizable components may be 30% by mass or more, 40% by mass or more, or 50% by mass or more, based on the total amount of the curable composition, and may be 99% by mass or less, 90% by mass or less, 80% by mass or less, 70% by mass or less, 60% by mass or less, or 50% by mass or less. 【0071】 The compounds represented by formula (1) and compounds copolymerizable with the compounds represented by formula (1) may be selected such that the crosslink density index calculated by the following formula (A) falls within the range described later. Crosslinking density index=M / C×1000…(A) In the formula, M represents the total number of moles of polymerizable groups (ethylenically unsaturated groups) in the polymerizable components, and C represents the total amount of polymerizable components contained in grams. 【0072】 The crosslinking density index may be, for example, 2.5 or less, and from the viewpoint of obtaining a heat storage material with even better reliability in high temperature and high humidity environments, it is preferably 2.0 or less, 1.8 or less, 1.6 or less, 1.4 or less, 1.2 or less, 1.0 or less, 0.8 or less, 0.6 or less, 0.5 or less, 0.4 or less, or 0.3 or less. The crosslinking density index may also be, for example, 0.1 or more, 0.2 or more, or 0.3 or more. 【0073】 If the curable composition contains a compound represented by formula (5), the curable composition preferably further contains a curing agent. The curing agent is a compound that can react with the reactive group contained in the compound represented by formula (5). 【0074】 Examples of curing agents include isocyanate-based curing agents, phenol-based curing agents, amine-based curing agents, imidazole-based curing agents, acid anhydride-based curing agents, and carboxylic acid-based curing agents. These curing agents are appropriately selected individually or in combination of two or more, depending on the type of reactive group contained in the compound represented by formula (5). For example, when the reactive group is an epoxy group, the curing agent is preferably a phenol-based curing agent or an imidazole-based curing agent. 【0075】 Examples of isocyanate-based curing agents include tolylene diisocyanate (2,4- or 2,6-tolylene diisocyanate, or mixtures thereof) (TDI), phenylene diisocyanate (m- or p-phenylene diisocyanate, or mixtures thereof), 4,4'-diphenyl diisocyanate, 1,5-naphthalene diisocyanate (NDI), diphenylmethane diisocyanate (4,4'-, 2,4'- or 2,2'-diphenylmethane diisocyanate, or mixtures thereof). Examples of aromatic diisocyanates include (MDI), 4,4'-toluidine diisocyanate (TODI), 4,4'-diphenyl ether diisocyanate, xylylene diisocyanate (1,3- or 1,4-xylylene diisocyanate, or mixtures thereof) (XDI), tetramethyl xylylene diisocyanate (1,3- or 1,4-tetramethyl xylylene diisocyanate, or mixtures thereof) (TMXDI), and ω,ω'-diisocyanate-1,4-diethylbenzene. 【0076】 Examples of isocyanate-based curing agents include trimethylene diisocyanate, 1,2-propylene diisocyanate, butylene diisocyanate (tetramethylene diisocyanate, 1,2-butylene diisocyanate, 2,3-butylene diisocyanate, 1,3-butylene diisocyanate), 1,5-pentamethylene diisocyanate (PDI), 1,6-hexamethylene diisocyanate (HDI), 2,4,4- or 2,2,4-trimethylhexamethylene diisocyanate, 2,6-diisocyanate methyl capeate and other aliphatic diisocyanates, 1,3-cyclopentane diisocyanate, 1,3-cyclopentene diisocyanate, cyclohexane diisocyanate (1,4-cyclohexane diisocyanate, 1,3-cyclohexane diisocyanate), and 3-isocyanatomethyl-3 Other examples include alicyclic diisocyanates such as ,5,5-trimethylcyclohexyl isocyanate (isophorone diisocyanate) (IPDI), methylenebis(cyclohexyl isocyanate) (4,4'-, 2,4'- or 2,2'-methylenebis(cyclohexyl isocyanate), their trans,trans-, trans,cis-, cis,cis-, or mixtures thereof) (H12MDI), methylcyclohexane diisocyanate (methyl-2,4-cyclohexane diisocyanate, methyl-2,6-cyclohexane diisocyanate), norbornane diisocyanate (various isomers or mixtures thereof) (NBDI), and bis(isocyanatomethyl)cyclohexane (1,3- or 1,4-bis(isocyanatomethyl)cyclohexane or mixtures thereof) (H6XDI). 【0077】 Examples of phenolic curing agents include bisphenol A, bisphenol F, bisphenol S, 4,4'-biphenylphenol, tetramethylbisphenol A, dimethylbisphenol A, tetramethylbisphenol F, dimethylbisphenol F, tetramethylbisphenol S, dimethylbisphenol S, tetramethyl-4,4'-biphenol, dimethyl-4,4'-biphenylphenol, 1-(4-hydroxyphenyl)-2-[4-(1,1-bis-(4-hydroxyphenyl)ethyl)phenyl]propane, 2,2'-methylene-bis(4-methyl-6-tert-butylphenol), 4,4'-butylidene-bis(3-methyl-6-tert-butylphenol), and trishydroxyphenylmeth Examples include phenol compounds having a diisopropylidene skeleton, such as resorcinol, hydroquinone, pyrogallol; phenol compounds having a fluorene skeleton such as 1,1-di-4-hydroxyphenylfluorene; cresol compounds; ethylphenol compounds; butylphenol compounds; octylphenol compounds; and various novolac resins made from phenols such as bisphenol A, bisphenol F, bisphenol S, and naphthol compounds, as well as xylylene skeleton-containing phenol novolac resins, dicyclopentadiene skeleton-containing phenol novolac resins, biphenyl skeleton-containing phenol novolac resins, fluorene skeleton-containing phenol novolac resins, and furan skeleton-containing phenol novolac resins. 【0078】 Examples of amine-based curing agents include aromatic amines such as diaminodiphenylmethane, diaminodiphenylsulfone, diaminodiphenyl ether, p-phenylenediamine, m-phenylenediamine, o-phenylenediamine, 1,5-diaminonaphthalene, and m-xylylenediamine; aliphatic amines such as ethylenediamine, diethylenediamine, hexamethylenediamine, isophoronediamine, bis(4-amino-3-methyldicyclohexyl)methane, and polyetherdiamine; and guanidine compounds such as dicyandiamide and 1-(o-tolyl)biguanide. 【0079】 Examples of imidazole-based curing agents include 2-methylimidazole, 2-ethyl-4-methylimidazole, 2-phenylimidazole, 2-undecylimidazole, 2-heptadecylimidazole, 2-phenyl-4-methylimidazole, 1-benzyl-2-phenylimidazole, 1-benzyl-2-methylimidazole, 1-cyanoethyl-2-methylimidazole, 1-cyanoethyl-2-phenylimidazole, 1-cyanoethyl-2-undecylimidazole, 2,3-dihydro-1H-pyrrolo-[1,2-a]benzimidazole, and 2,4-diamino-6(2'-methylimidazole(1'))ethyl-s-triazine Examples include 2,4-diamino-6(2'-undecylimidazole(1'))ethyl-s-triazine, 2,4-diamino-6(2'-ethyl-4-methylimidazole(1'))ethyl-s-triazine, 2,4-diamino-6(2'-methylimidazole(1'))ethyl-s-triazine isocyanurate adduct, 2-methylimidazole isocyanurate adduct, 2-phenylimidazole isocyanurate adduct, 2-phenyl-3,5-dihydroxymethylimidazole, 2-phenyl-4-methyl-5-hydroxymethylimidazole, and 1-cyanoethyl-2-phenyl-3,5-dicyanoethoxymethylimidazole. 【0080】 Examples of acid anhydride-based curing agents include aromatic carboxylic acid anhydrides such as phthalic anhydride, trimellitic anhydride, pyromellitic anhydride, benzophenonetetracarboxylic anhydride, ethylene glycol trimellitic anhydride, and biphenyltetracarboxylic anhydride; aliphatic carboxylic acid anhydrides such as azelaic acid, sebacic acid, and dodecanedioic acid; and alicyclic carboxylic acid anhydrides such as tetrahydrophthalic anhydride, hexahydrophthalic anhydride, nasic anhydride, hetic anhydride, and hymicic anhydride. 【0081】 Examples of carboxylic acid-based curing agents include succinic acid, glutaric acid, adipic acid, sebacic acid, phthalic acid, isophthalic acid, and terephthalic acid. 【0082】 The hardening agent content may be 0.01% by mass or more, and may be 10% by mass or less, 5% by mass or less, or 1% by mass or less, based on the total amount of the curable composition. 【0083】 The curable composition may further contain heat-storing capsules from the viewpoint of obtaining a heat-storing material with even better heat storage capacity. The heat-storing capsule has a heat-storing component and an outer shell that encloses the heat-storing component. 【0084】 The heat-storing components in the heat-storing capsule are appropriately selected, for example, those having a phase transition temperature suitable for the target temperature depending on the intended use. Other heat-storing components have a solid / liquid phase transition point (melting point) that exhibits a solid / liquid phase transition between -30 and 120°C, from the viewpoint of obtaining a heat storage effect within a practical range. 【0085】 The heat-storing component may be, for example, a linear (linear or branched (branched-chain)) saturated hydrocarbon compound (paraffinic hydrocarbon compound), polyalkylene glycol, natural wax, petroleum wax, sugar alcohol, etc. From the viewpoint of being inexpensive, having low toxicity, and being easily selectable for the desired phase transition temperature, the other heat-storing component is preferably a linear saturated hydrocarbon compound (paraffinic hydrocarbon compound). 【0086】 Chain-like saturated hydrocarbon compounds include, specifically, n-decane (C10 (number of carbon atoms, same applies below), -29°C (transition point (melting point), same applies below)), n-undecane (C11, -25°C), n-dodecane (C12, -9°C), n-tridecane (C13, -5°C), n-tetradecane (C14, 6°C), n-pentadecane (C15, 9°C), n-hexadecane (C16, 18°C), n-heptadecane (C17, 21°C), n-octadecane (C18, 28°C), n-nanodecane (C19, 32°C), n-eicosane (C20, 37°C), n-heicosane (C21, These may be n-docosane (C22, 46°C), n-tricosane (C23, 47°C), n-tetracosane (C24, 50°C), n-pentacosane (C25, 54°C), n-hexacosane (C26, 56°C), n-heptacosane (C27, 60°C), n-octacosane (C28, 65°C), n-nonacosane (C29, 66°C), n-triacontane (C30, 67°C), n-tetracontane (C40, 81°C), n-pentacontane (C50, 91°C), n-hexacontane (C60, 98°C), n-hectan (C100, 115°C), etc. The linear saturated hydrocarbon compounds may be branched saturated hydrocarbon compounds having the same number of carbon atoms as these linear saturated hydrocarbon compounds. The chain-like saturated hydrocarbon compound may be one or more of these. 【0087】 The outer shell containing the heat-storing component is preferably made of a material having a heat resistance temperature sufficiently higher than the transition point (melting point) of the heat-storing component. The material forming the outer shell has a heat resistance temperature of, for example, 30°C or higher, preferably 50°C or higher, relative to the transition point (melting point) of the heat-storing component. The heat resistance temperature is defined as the temperature at which the weight loss of the capsule reaches 1% when measured using a differential thermogravimetric analyzer (e.g., TG-DTA6300 (manufactured by Hitachi High-Tech Science Co., Ltd.)). 【0088】 As the material forming the outer shell, a material having strength appropriate to the application of the heat storage material formed by the curable composition is appropriately selected. The outer shell may preferably be formed of melamine resin, acrylic resin, urethane resin, silica, etc. Examples of microcapsules having an outer shell containing melamine resin include BA410xxP,6C, BA410xxP,18C, BA410xxP,37C from Outlast Technologies, Ltd., Thermo Memory FP-16, FP-25, FP-31, FP-39 from Mitsubishi Paper Mills Ltd., and Riken Resin PMCD-15SP, 25SP, 32SP from Miki Riken Kogyo Co., Ltd. Examples of microcapsules having an outer shell containing acrylic resin (polymethyl methacrylate resin) include Micronal DS5001X, 5040X from BASF. Examples of microcapsules having an outer shell containing silica include Riken Resin LA-15, LA-25, LA-32 from Miki Riken Kogyo Co., Ltd. 【0089】 From the viewpoint of further enhancing the heat storage effect, the content of the heat-storing component in the heat-storing capsule is preferably 20% by mass or more, more preferably 60% by mass or more, based on the total amount of the heat-storing capsule, and from the viewpoint of suppressing capsule damage due to volume changes of the heat-storing component, it is preferably 80% by mass or less. 【0090】 The heat-storing capsule may further contain graphite, metal powder, alcohol, etc., inside its outer shell for the purpose of adjusting the thermal conductivity, specific gravity, etc., of the capsule. 【0091】 The particle size (average particle size) of the heat-storing capsule is preferably 0.1 μm or more, more preferably 0.2 μm or more, even more preferably 0.5 μm or more, preferably 100 μm or less, and more preferably 50 μm or less. The particle size (average particle size) of the heat-storing capsule is measured using a laser diffraction particle size distribution analyzer (for example, SALD-2300 (manufactured by Shimadzu Corporation)). 【0092】 From the viewpoint of further enhancing the heat storage effect, the content of heat-storing capsules 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 total amount of the curable composition. From the viewpoint of suppressing the detachment of heat-storing capsules from the cured product of the curable composition, the content of heat-storing capsules 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 total amount of the curable composition. 【0093】 The curable composition may further contain an antioxidant from the viewpoint of improving the thermal reliability of the cured product (heat storage material) of the curable composition. The antioxidant may be, for example, a phenolic antioxidant, a benzophenone antioxidant, a benzoate antioxidant, a hindered amine antioxidant, a benzotriazole antioxidant, and the like. 【0094】 The antioxidant content may be 0.1% by mass or more, 0.5% by mass or more, 0.8% by mass or more, or 1% by mass or more, based on the total amount of the curable composition, and may be 10% by mass or less or 5% by mass or less. From the viewpoint of excellent flexibility of the cured product of the curable composition, it is preferably 4% by mass or less, more preferably 3% by mass or less, even more preferably 2.5% by mass or less, and particularly preferably 2% by mass or less. 【0095】 The curable composition may further contain other additives as needed. Examples of other additives include surface treatment agents, curing accelerators, colorants, fillers, nucleating agents, heat stabilizers, heat conductive materials, plasticizers, foaming agents, flame retardants, vibration dampers, dehydrating agents, and flame retardant aids (e.g., metal oxides). These other additives may be used individually or in combination of two or more. The content of these other additives may be 0.1% by mass or more and 30% by mass or less based on the total amount of the curable composition. 【0096】 The curable composition may be liquid at 50°C. This allows the curable composition to be easily provided even between components with complex shapes by methods such as filling. In this case, the viscosity of the curable composition at 50°C is preferably 100 Pa·s or less, more preferably 50 Pa·s or less, even more preferably 20 Pa·s or less, and particularly preferably 10 Pa·s or less, and may be, for example, 0.5 Pa·s or more, from the viewpoint of excellent fluidity and handling properties. The viscosity of the curable composition refers to the value measured according to JIS Z8803, and specifically refers to the value measured by an E-type viscometer (for example, PE-80L manufactured by Toki Sangyo Co., Ltd.). The viscometer can be calibrated according to JIS Z8809-JS14000. 【0097】 The curable composition described above makes it possible to form a heat storage material with excellent reliability in high-temperature and high-humidity environments by using in combination a compound represented by formula (1) having two (meth)acryloyl groups and a compound in which at least one terminal hydroxyl group of the polyalkylene glycol is etherified. This is presumed to be because, when the curable composition is cured, the polyalkylene glycol ether, whose reliability in high-temperature and high-humidity environments is improved due to the etherification of the terminal hydroxyl groups, is well incorporated into the crosslinked structure formed from the compound represented by formula (1), and the synergistic effect of these improves resistance to external moisture. Furthermore, the cured product of the curable composition can have excellent heat storage capacity due to the compound represented by formula (1) and the polyoxyalkylene chain in the polyalkylene glycol ether. Therefore, this curable composition is suitable as a curable composition used to form a heat storage material, and the cured product of the curable composition is suitable for use as a heat storage material. 【0098】 [Heat storage material] One embodiment of the heat storage material includes a cured product of the curable composition described above. Figure 1 is a schematic cross-sectional view showing one embodiment of the heat storage material. As shown in Figure 1(a), the heat storage material 1A according to one embodiment is a sheet-like (or film-like) heat storage material comprising a heat storage layer 2 which is a cured product of the curable composition described above. 【0099】 As shown in Figure 1(b), the heat storage material 1B according to another embodiment is a sheet-like (or film-like) heat storage material comprising a heat storage layer 2 which is a cured product of the curable composition described above, and an adhesive layer 3 provided on one surface of the heat storage layer 2. In this case, the heat storage material 1B can be suitably adhered to the target to which the heat storage material 1B is applied. 【0100】 In each of the embodiments described above, the thickness of the heat storage layer 2 may be, for example, 0.01 mm or more, 0.05 mm or more, 0.1 mm or more, or 0.2 mm or more, and may be 20 mm or less, 10 mm or less, or 5 mm or less. 【0101】 In each of the above embodiments, the heat storage layer 2 may be a cured product in which the curable composition has been completely cured, or it may be a cured product in which the curable composition has been B-staged (partially cured). In the heat storage material 1A shown in Figure 1(a), from the viewpoint of being able to suitably adhere the heat storage material 1A to the application target, the heat storage layer 2 is preferably a cured product in which the curable composition has been B-staged (partially cured). 【0102】 The adhesive layer 3 may be composed of a known adhesive. The thickness of the adhesive layer 3 may be, for example, 0.001 mm or more, 0.003 mm or more, or 0.005 mm or more, and may be 0.03 mm or less, 0.02 mm or less, or 0.015 mm or less. 【0103】 Heat storage materials 1A and 1B (collectively referred to as heat storage material 1) can be used in a variety of fields. Heat storage material 1 can be used, for example, in air conditioning equipment in automobiles, buildings, public facilities, underground shopping areas (to improve the efficiency of air conditioning equipment), piping in factories (to store heat in the piping), automobile engines (to keep the area around the engine warm), electronic components (to prevent the temperature of electronic components from rising), and underwear fibers. 【0104】 The heat storage layer 2 in the heat storage material 1A described above, or the heat storage layer 2 and adhesive layer 3 in the heat storage material 1B, may be provided on a support film. That is, the heat storage material according to another embodiment may comprise a support film and a heat storage layer 2 provided on the support film. The heat storage material according to another embodiment may comprise a support film, a heat storage layer 2 provided on the support film, and an adhesive layer 3 provided on the side of the heat storage layer 2 opposite to the support film. The heat storage materials according to these embodiments may, for example, be formed in a long shape and wound around a core along its longitudinal direction (roll-shaped heat storage material). 【0105】 The support film may be formed from polymers such as polyethylene terephthalate, polyethylene, polyvinylidene chloride, polyester, polypropylene, polyvinyl chloride, polycarbonate, polyacrylonitrile, polyether ether ketone, polyvinyl alcohol, ethylene-vinyl alcohol copolymer, polyimide, and polyamide-imide. 【0106】 The thickness of the support film may be, for example, 10 μm or more, 30 μm or more, or 50 μm or more, and may be 200 μm or less, 150 μm or less, 100 μm or less, 70 μm or less, or 50 μm or less. 【0107】 [Articles and methods for manufacturing the same] Next, we will explain an article equipped with a heat storage material 1 (a cured product of a curable composition) and a method for manufacturing the same, using an electronic component as an example of an object to which the heat storage material 1 is provided. 【0108】 Figure 2 is a schematic cross-sectional view showing one embodiment of an article and a method for manufacturing the same. In the method for manufacturing an article according to one embodiment, first, as shown in Figure 2(a), an electronic component 11A is prepared as the article to which the heat storage material will be placed. The electronic component 11A comprises, for example, a substrate 12 and a semiconductor chip (heat source) 13 provided on the substrate 12. 【0109】 Next, as shown in Figure 2(b), the sheet-shaped heat storage material 1 is placed on the substrate 12 and the semiconductor chip 13 so as to be in thermal contact with the substrate 12 and the semiconductor chip 13, respectively. The heat storage material 1 may be, for example, the heat storage material 1A shown in Figure 1(a) above, or the heat storage material 1B shown in Figure 1(b) above. When using the heat storage material 1B shown in Figure 1(b), the heat storage material 1B is placed so that the adhesive layer 3 is in contact with the substrate 12 and the semiconductor chip 13. 【0110】 If the heat storage layer in the heat storage material 1 is a cured product in which the curable composition has been B-staged (partially cured), the heat storage layer is cured after the heat storage material 1 is placed. That is, the method for manufacturing the article of this embodiment may further include a step of curing the heat storage layer of the heat storage material 1 placed on the substrate 12 and semiconductor chip 13. 【0111】 This results in an article 14A comprising a substrate 12, a semiconductor chip 13, and a heat storage material 1 (a cured product of a curable composition) provided on the substrate 12 and the semiconductor chip 13. 【0112】 In the above embodiment, the heat storage material 1 is arranged to cover the entire exposed surface of the heat source 13, but in another embodiment, the heat storage material may be arranged to cover only a portion of the exposed surface of the heat source. 【0113】 Figure 3(a) is a schematic cross-sectional view showing another embodiment of the article. As shown in Figure 3(a), in the article 14B according to another embodiment, the heat storage material 1 may be positioned, for example, in contact with (covering) a portion of the exposed surface of the semiconductor chip (heat source) 13. The location where the heat storage material 1 is positioned (the location where the heat storage material 1 contacts the semiconductor chip 13) is the side portion of the semiconductor chip 13 in Figure 3(a), but it may be on any surface of the semiconductor chip 13. 【0114】 Figure 3(b) is a schematic cross-sectional view showing another embodiment of the article. As shown in Figure 3(b), in article 14C according to another embodiment, the heat storage material 1 is arranged on the surface of the substrate 12 opposite to the surface on which the semiconductor chip 13 is provided. In this embodiment, the heat storage material 1 is not in direct contact with the semiconductor chip 13, but is in thermal contact with the semiconductor chip 13 via the substrate 12. The location where the heat storage material 1 is placed may be on any surface of the substrate 12, as long as it is in thermal contact with the semiconductor chip 13. Even in this case, the heat generated by the heat source (semiconductor chip) 13 is efficiently conducted to the heat storage material 1 via the substrate 12 and is suitably stored in the heat storage material 1. 【0115】 In the manufacturing method according to the above embodiment, the heat storage material 1 is in the form of a sheet, but in the manufacturing method according to another embodiment, an article can also be manufactured (formed a heat storage material) using a liquid curable composition. 【0116】 Figure 4 is a schematic cross-sectional view showing another embodiment of the method for manufacturing an article. In the manufacturing method according to this embodiment, first, as shown in Figure 4(a), an electronic component 11B is prepared as the article to which the heat storage material will be placed. The electronic component 11B includes, for example, a substrate (e.g., a circuit board) 12, a semiconductor chip (heat source) 13 provided on the substrate 12, and a plurality of connection parts (e.g., solder) 15 that connect the semiconductor chip 13 to the substrate 12. The plurality of connection parts 15 are provided between the substrate 12 and the semiconductor chip 13, spaced apart from each other. That is, there are gaps between the substrate 12 and the semiconductor chip 13 that separate the plurality of connection parts 15 from each other. 【0117】 Next, as shown in Figure 4(b), the curable composition 21 is filled between the substrate 12 and the semiconductor chip 13 using, for example, a syringe 16. The curable composition 21 is the curable composition according to the embodiment described above. The curable composition 21 may be completely uncured or partially cured. 【0118】 If the curable composition 21 is in a liquid state at room temperature (e.g., 25°C), it can be filled at room temperature. If the curable composition 21 is in a solid state at room temperature, it can be heated (e.g., to 50°C or higher) to make it liquid before being filled. 【0119】 As described above, by filling the gap between the substrate 12 and the semiconductor chip 13 with the curable composition 21, the curable composition 21 is positioned in thermal contact with the substrate 12, the semiconductor chip 13, and the connection portion 15, as shown in Figure 4(c). 【0120】 Next, by curing the curable composition 21, a cured product of the curable composition (which can also be called a heat storage layer or heat storage material) 22 is formed in the gap between the substrate 12 and the semiconductor chip 13, as shown in Figure 4(d). In this way, an article 14D is obtained comprising a substrate 12, a semiconductor chip (heat source) 13 provided on the substrate 12, a plurality of connection parts 15 connecting the semiconductor chip 13 to the substrate 12, and a cured product of the curable composition (heat storage layer or heat storage material) 22 provided to fill the gap formed by the substrate 12, the semiconductor chip (heat source) 13, and the plurality of connection parts 15. 【0121】 The curing method for the curable composition 21 may be, if the curable composition 21 contains a thermal polymerization initiator, a method of curing the curable composition 21 by heating the arranged curable composition 21. The curing method for the curable composition 21 may be, if the curable composition 21 contains a photopolymerization initiator, a method of curing the curable composition 21 by irradiating the curable composition 21 with light (for example, light including at least a portion of the wavelengths between 200 and 400 nm (ultraviolet light)). The curing method may be any one of these methods or a combination of two or more of them. 【0122】 In each of the above embodiments, the heat storage material 1 (cured product 22 of the curable composition) is arranged so as to be in direct contact with the semiconductor chip 13, which is the heat source. However, the heat storage material and the cured product of the curable composition only need to be in thermal contact with the heat source, and in another embodiment, for example, they may be arranged so as to be in thermal contact with the heat source via a thermally conductive member (such as a heat dissipation member). [Examples] 【0123】 The present invention will be described in more detail below with reference to examples, but the present invention is not limited to the following examples. 【0124】 [Synthesis of compound (A-1)] A 500 mL flask, consisting of a stirrer, thermometer, nitrogen gas inlet tube, outlet tube, and heating jacket, was used as the reactor. 15 g of polyethylene glycol #1000 (weight-average molecular weight: 1000, manufactured by Sanyo Chemical Industries, Ltd.) and 300.0 g of toluene were added to the reactor and stirred at 45°C and a stirring speed of 250 revolutions / minute. Nitrogen was supplied at a rate of 100 mL / min and stirred for 30 minutes. The temperature was then lowered to 25°C, and after cooling was complete, 2.9 g of acryloyl chloride was added dropwise to the reactor and stirred for 30 minutes. Then, 3.8 g of triethylamine was added dropwise and stirred for 2 hours. The temperature was then raised to 45°C and the reaction was carried out for 2 hours. The reaction solution was filtered, and the filtrate was desoluble to obtain compound (A-1), which is represented by the following formula (1-3) and has a weight-average molecular weight of 1000. [ka] 【0125】 [Synthesis of compound (A-2)] Compound (A-2), which is represented by the above formula (1-3) and has a weight-average molecular weight of 3400, was obtained in the same manner as compound (A-1), except that 45 g of polyethylene glycol 4,000 (weight-average molecular weight: 2700-3300, manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) was used instead of 15 g of polyethylene glycol #1000. 【0126】 [Synthesis of compound (A-3)] Compound (A-3), which is represented by the above formula (1-3) and has a weight-average molecular weight of 8000, was obtained in the same manner as compound (A-1), except that 120 g of polyethylene glycol 6,000 (weight-average molecular weight: 7300-9300, manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) was used instead of 15 g of polyethylene glycol #1000. 【0127】 In the examples, in addition to the above compounds (A-1) to (A-3), the following components were used. (B-1) Polyethylene glycol monomethyl ether (weight-average molecular weight: 1000) (B-2) Polyethylene glycol dimethyl ether (weight-average molecular weight: 1000) (B-3) Polyethylene glycol monomethyl ether (weight-average molecular weight: 4000) (b-1) Polyethylene glycol (weight-average molecular weight: 1000) (C-1) Methoxypolyethylene glycol acrylate (weight-average molecular weight: 550) (C-2) Methoxypolyethylene glycol acrylate (weight-average molecular weight: 1000) (D-1) Antioxidant (Adeka Stab AO-80, manufactured by Adeka Co., Ltd.) (D-2) Polymerization initiator (Omnirad1173, manufactured by IGM Resins BV) 【0128】 [Manufacturing of heat storage materials] Each component was heated and mixed at 70°C according to the mixing ratios shown in Tables 1 and 2 to obtain the curable compositions for the Examples and Reference Examples. Next, under conditions of 70°C, the curable composition was applied onto a PET film using a spacer so that the thickness after curing was 200 μm, and then another PET film was placed over the applied surface. An illuminance of 130 mW / cm² was then applied using a metal halide lamp manufactured by Ushio Inc. 2 , cumulative light intensity 4000 mJ / cm 2 The material was irradiated with UV light in the manner described above to obtain a heat storage material (cured product of a curable composition). 【0129】 [Reliability testing under high temperature and high humidity conditions] Three 30mm x 30mm samples were cut from each of the heat storage materials (cured products) in the examples and reference examples, and their weights (initial weights) were measured. These samples were left to stand for 1 hour in an environment of 85°C and 85% RH. Upon visual inspection of the surface of each sample after standing, seepage of liquid components was observed on the surfaces of Reference Example 1 and Examples 1-2, 4-5, and 9. For each sample in which seepage was observed, the liquid components on the surface were wiped off with Kimwipes (manufactured by Nippon Paper Crecia Co., Ltd.), and the weights (post-test weights) of the three samples were measured. The average value of the weight change rate for the three samples was calculated using the following formula. Weight change rate (%) = (Weight after test - Initial weight) / Initial weight × 100 Furthermore, for the remaining examples where no liquid component seepage was observed, the weight (post-test weight) of each of the three samples was measured, and the average weight change rate, calculated using the above formula, was calculated for the three samples. The weight change rates calculated in this manner are shown in Tables 1 and 2. 【0130】 [Measurement of heat storage capacity] For each heat storage material (cured product) in the examples, the amount of heat stored was calculated by measurement using a differential scanning calorimetry meter (TA Instruments, model number Discovery DSC250). Specifically, the temperature was raised to 100°C at 20°C / min, held at 100°C for 3 minutes, then cooled to -20°C at a rate of 3°C / min, held at -20°C for 3 minutes, and then raised again to 100°C at a rate of 3°C / min to measure the thermal behavior of each heat storage material. The area of ​​the melting peak was calculated as the amount of heat stored. The results are shown in Tables 1 and 2. 【0131】 [Table 1] 【0132】 [Table 2] 【0133】 A negative weight change rate indicates that a liquid component has seeped out onto the sample surface, and in this case, a larger absolute value indicates a greater amount of seepage. This liquid component is thought to be polyethylene glycol or polyethylene glycol ether. On the other hand, a positive weight change rate indicates that no liquid component has seeped out onto the sample surface, and that the heat storage material has absorbed and contained moisture in a high-temperature, high-humidity environment. In other words, a positive weight change rate is more reliable under high-temperature, high-humidity conditions than a negative value, and if the weight change rate is negative, a smaller absolute value indicates better reliability under high-temperature, high-humidity conditions. As can be seen from Tables 1 and 2, Examples 1 to 13, which use the compound represented by formula (1) in combination with polyalkylene glycol ether, are more reliable under high-temperature, high-humidity conditions than Reference Example 1, which uses the compound represented by formula (1) in combination with polyalkylene glycol. [Explanation of Symbols] 【0134】 1, 1A, 1B... Heat storage material, 2... Heat storage layer, 3... Adhesive layer, 11A, 11B... Electronic component, 12... Substrate, 13... Semiconductor chip (heat source), 14A, 14B, 14C, 14D... Article, 15... Connection part, 16... Syringe, 21... Curable composition, 22... Cured product of curable composition (heat storage material).

Claims

[Claim 1] The compound represented by the following formula (1), A curable composition containing at least one polyalkylene glycol ether selected from the group consisting of polyalkylene glycol monoethers and polyalkylene glycol diethers. 【Chemistry 1】 [In formula (1), R １１ and R １２ Each of these independently represents a hydrogen atom or a methyl group, R １３ This represents a divalent group having a polyoxyalkylene chain.

Images