Latent heat storage material, latent heat storage body, electronic device, and electricity storage device

Abstract

To provide a latent heat storage material using latent heat accompanying a phase change from a solid phase to a solid phase which has a phase change temperature of 60°C or lower and has a large latent heat amount, and repeating characteristics, a latent heat storage body, an electronic device, and a power storage device.SOLUTION: There are provided a latent heat storage material containing a compound represented by the following formula (I), and application of the same. In the formula (I), as for n and m, in the case of n=m, n represents an odd number, in the case of n≠m, n and m each independently represents an integer of 6 to 24, and X- represents an anion.SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present disclosure relates to a latent heat storage material, a latent heat storage body, an electronic device, and an electricity storage device. [Background technology]

[0002] In recent years, the rapid spread of digital home appliances has led to a steady increase in heat generated by electronic devices that handle large amounts of information at high speeds. Furthermore, as devices become smaller, lighter, and thinner, the importance of efficient heat dissipation measures is growing. Mobile devices, such as smartphones and tablet PCs (personal computers), are becoming increasingly sophisticated and powerful despite their compact size, resulting in a significant increase in heat density. In mobile devices, the increased heat density poses a growing risk of thermal runaway and accelerated solder fatigue due to thermal cycling, necessitating heat management measures to improve reliability.

[0003] Passive cooling methods using phase change materials (PCMs) are gaining attention as a cooling method for electronic devices. PCMs are also known as latent heat storage materials, and because they can absorb heat with almost no change in temperature, they have the effect of slowing down the time it takes for the temperature to rise, a so-called delay effect. Latent heat storage materials utilize the heat absorption and release that occurs when a substance changes state, and have the advantage of being reusable and having a larger heat storage capacity than other heat storage materials. Examples of latent heat storage materials include paraffin (melting point: 36.4°C (eicosane: C 20 H 42 ), sodium acetate trihydrate (melting point: 58°C), erythritol (melting point: 119°C), etc. are known as latent heat storage materials. 1-hexadecyl-3-methylimidazolium chloride, an imidazole-based ionic liquid, is also known as a latent heat storage material (see, for example, Non-Patent Documents 1 and 2). All of these compounds are latent heat storage materials that utilize the latent heat of fusion that accompanies a phase change from a solid phase to a liquid phase.

[0004] When a latent heat storage material that utilizes the latent heat of fusion that accompanies a phase change from solid to liquid as described above is used to cool a mobile device, a problem can arise in that the melted and liquid latent heat storage material leaks out of the mobile device. One method for solving this problem is to microencapsulate the latent heat storage material. However, microencapsulating a latent heat storage material has the drawback of reducing the amount of latent heat per unit volume. A reduction in the amount of latent heat per unit volume is a factor that hinders the slimming of mobile devices. On the other hand, a latent heat storage material that does not have the problem of leakage is one that utilizes the latent heat that accompanies a phase change from solid to solid. Examples of such latent heat storage materials include those represented by the formula (C n H 2n+1 )2N + H2NO3 - Dialkylammonium nitrates represented by the following formula (where n is an even number of 8 to 19) are known (see, for example, Non-Patent Document 3).

[0005] In recent years, electric vehicles equipped with high-performance batteries have become increasingly popular in order to utilize energy more efficiently. Lithium-ion batteries, in particular, have been actively developed as high-performance batteries for use in electric vehicles, and efforts are being made to increase the power output and capacity of lithium-ion batteries. However, the excessively high temperatures caused by high power output and the large amounts of heat generated during charging and discharging associated with high capacity can significantly shorten the battery's lifespan and, in the worst case, can even lead to the risk of fire and explosion. Generally, lithium-ion batteries tend to show significant performance degradation at operating temperatures above 60°C. Therefore, thermal management techniques that maintain the battery temperature within an optimal temperature range (e.g., 15°C to 60°C) are essential for optimizing battery characteristics, extending battery life, and improving battery safety. In this regard, the dialkylammonium nitrate described in Non-Patent Document 3 has a high latent heat per unit volume, but tends to have a high phase change temperature (also referred to as "phase transition temperature"), making it unsuitable as a latent heat storage material for batteries. [Prior art documents] [Non-patent literature]

[0006] [Non-Patent Document 1] E.Thomas, D.Thomas, S. Bhuvaneswari, KPVijayalakshmi, BKGeorge, “1-Hexadecyl-3-methylimidazolium chloride: Structure, thermal stability and decomposition mechanism”, J.Mol. Liq., vol. 249(2018), pp. 404-411. [Non-patent document 2] M. Bendovaa, M. Canjia, M.G. Bogdanovb, Z. Wagnera, N. Zdolsekc, F. Quirion, “Phase Transitions in Higher-Melting Ionic Liquids: Thermal Storage Materials or Liquid Crystals?” Chemical Engineering Transactions Vol. 69, (2018) ISBN 978-88-95608-66-2 (The penultimate “a” in the author’s name “M. Bendovaa” is an “a” with a charka, the “C” in “M. Canjia” is an “C” with a charka, and the “s” in “N. Zdolsekc” is an “s” with a charka.) [Non-patent document 3] S. Steinert, W. Voigt, R. Glausch, M. Neuschutz, “Thermal characteristics of solid-solid phase transitions in long-chain dialkyl ammonium salts” Thermochimica Acta vol. 435 (2005) pp. 28-33. Summary of the Invention [Problem to be solved by the invention]

[0007] As described above, latent heat storage materials are required to have a low phase change temperature of 60°C or less, a large amount of latent heat, and to avoid the problem of leakage due to melting accompanying the phase change. Furthermore, latent heat storage materials are required to have the property of repeatedly absorbing and releasing heat (so-called repetitive properties).

[0008] The present disclosure has been made in consideration of the above circumstances. The problem that one embodiment of the present disclosure aims to solve is to provide a latent heat storage material that utilizes the latent heat associated with a phase change from solid to solid, and that has a low phase change temperature of 60°C or less, a large amount of latent heat, and repeatability. Another problem to be solved by another embodiment of the present disclosure is to provide a latent heat storage body including the latent heat storage material, and an electronic device and an electricity storage device including the latent heat storage material. [Means for solving the problem]

[0009] In the course of extensive research to solve the above-mentioned problems, the present inventors focused on dialkylammonium salts, which are latent heat storage materials that utilize the latent heat associated with solid-to-solid phase changes. After extensive research on dialkylammonium salts, they discovered that when the carbon numbers of the two alkyl chains of a dialkylammonium salt are the same, an odd-numbered carbon atom has a lower phase change temperature and a larger latent heat capacity than an even-numbered carbon atom. Furthermore, they discovered that by setting the carbon numbers of the two alkyl chains to specific different values, the phase change temperature of a dialkylammonium salt can be lowered without reducing the latent heat capacity, leading to the completion of the present disclosure.

[0010] Specific means for solving the above problems include the following aspects. <1> A latent heat storage material comprising a compound represented by the following formula (I):

[0011] [ka]

[0012] In formula (I), when n=m, n represents an odd number, and when n≠m, n and m each independently represent an integer of 6 to 24. X - represents an anion.

[0013] <2> In the above formula (I), n and m are equal to m, and n is an odd number between 5 and 17. <1> The latent heat storage material according to claim 1. <3> In the above formula (I), n and m are equal to m, and n is an odd number between 7 and 13. <1> The latent heat storage material according to claim 1. <4> In the above formula (I), n and m are n≠m, and n and m each independently represent an integer of 7 to 14. <1> The latent heat storage material according to claim 1. <5> X in the above formula (I) - represents a nitrate ion or a chlorate ion <1> ~ <4> 10. The latent heat storage material according to claim 9, wherein the latent heat storage material is a latent heat storage material. <6> Phase change temperature is 60°C or less <1> ~ <5> 10. The latent heat storage material according to claim 9, wherein the latent heat storage material is a latent heat storage material. <7> Used in electronic devices or power storage devices <1> ~ <6> 10. The latent heat storage material according to claim 9, wherein the latent heat storage material is a latent heat storage material. <8> <1> ~ <6> 10. A latent heat storage medium comprising the latent heat storage material according to any one of the above items. <9> <1> ~ <6> 1. An electronic device comprising the latent heat storage material according to any one of the above. <10> <1> ~ <6> 10. An electricity storage device comprising the latent heat storage material according to any one of the above items. [Effects of the Invention]

[0014] According to one embodiment of the present disclosure, there is provided a latent heat storage material that utilizes the latent heat associated with a phase change from solid to solid, and that has a low phase change temperature of 60°C or less, a large amount of latent heat, and repeatability. According to other embodiments of the present disclosure, there are provided a latent heat storage body including the latent heat storage material, and an electronic device and an electricity storage device including the latent heat storage material. [Brief explanation of the drawings]

[0015] [Figure 1] 1 is a graph showing the relationship between the number of carbon atoms n (n=m in formula (I)) and the amount of latent heat in the compounds of Examples 1 to 4 and Comparative Examples 1 to 5. [Figure 2] 1 is a graph showing the relationship between the carbon numbers n and m of the compounds in Examples 5 to 7 and Comparative Example 3 and the phase change temperature and the amount of latent heat. [Figure 3] 1 is a graph showing the relationship between the carbon numbers n and m of the compounds in Examples 8 to 10 and Comparative Example 4 and the phase change temperature and the amount of latent heat. [Figure 4] 1 is a graph showing the relationship between the carbon numbers n and m of the compounds in Examples 11 and 12 and Comparative Example 6 and the phase change temperature and the amount of latent heat. [Figure 5] 1 is a graph showing the X-ray diffraction spectrum of Compound 2 obtained in Synthesis Example 2. DETAILED DESCRIPTION OF THE INVENTION

[0016] The latent heat storage material of the present disclosure, the latent heat storage medium containing the latent heat storage material, and the electronic device and the power storage device including the latent heat storage material will be described in detail below. The explanation of the requirements described below may be based on a representative embodiment of the present disclosure, but the present disclosure is not limited to such an embodiment and can be implemented with appropriate modifications within the scope of the purpose of the present disclosure.

[0017] In the present disclosure, a numerical range indicated using "to" means a range that includes the numerical values ​​before and after "to" as the lower and upper limits, respectively. In the numerical ranges described in stages in the present disclosure, the upper or lower limit value described in a certain numerical range may be replaced with the upper or lower limit value of another numerical range described in stages. Furthermore, in the numerical ranges described in the present disclosure, the upper or lower limit value described in a certain numerical range may be replaced with a value shown in the examples.

[0018] In the present disclosure, a combination of two or more preferred embodiments is a more preferred embodiment. In the present disclosure, when the latent heat storage material contains a plurality of substances corresponding to each component, the amount of each component in the latent heat storage material means the total amount of the plurality of substances present in the latent heat storage material unless otherwise specified. The same applies to the latent heat storage body.

[0019] [Latent heat storage material] The latent heat storage material of the present disclosure contains the compound represented by the above-mentioned formula (I). The latent heat storage material disclosed herein is a latent heat storage material that utilizes the latent heat associated with a phase change from solid to solid, has a low phase change temperature of 60°C or less, a large amount of latent heat, and has repeatability.

[0020] The present inventors have found that when the carbon numbers of the two alkyl chains of a dialkylammonium salt are the same, the phase change temperature is lower and the latent heat is larger when the carbon number is odd compared to when the carbon number is even. Furthermore, they have found that the phase change temperature of a dialkylammonium salt can be lowered without reducing the latent heat by adjusting the carbon numbers of the two alkyl chains to specific different values.

[0021] The latent heat storage material of the present disclosure is n H 2n+1 )2N + H2NO3 - Dialkylammonium nitrates represented by the formula (where n is an even number between 8 and 19) have the same even number of carbon atoms in the two alkyl chains, and although the latent heat is large, the phase change temperature tends to be high. In the case of dialkylammonium nitrates in which the carbon atoms in the two alkyl chains are the same even number, the phase change temperature and latent heat are related to the value of n (i.e., the number of carbon atoms in the alkyl chains), and as the value of n becomes smaller, the phase change temperature decreases, but the latent heat also decreases, creating a trade-off relationship. Furthermore, in the case of dialkylammonium nitrates in which the carbon atoms in the two alkyl chains are the same even number, a small value of n means that the cyclic property is not exhibited.

[0022] It is known that the enthalpy change of dialkylammonium salts is strongly related to the symmetry of the alkyl chain (see, for example, MJM van Oort, MA White, Ber. Bunsenges. Phys. Chem. 92 (1988) 168.). It is also known that the properties of organic compounds change depending on whether the number of carbon atoms is even or odd (the so-called odd-even effect) (see, for example, F. Tao, SL Bernasek, "Understanding Odd-Even Effects in Organic Self-Assembled Monolayers," Chem. Rev. 2007, Vol. 107, pp. 1408-1453.). However, predicting the effect of the even or odd carbon number on latent heat is difficult. For example, in the case of long-chain alkanes, an odd-even effect is observed in latent heat, with the latent heat of long-chain alkanes with even carbon numbers being larger than that of long-chain alkanes with odd carbon numbers. However, it has been reported that no odd-even effect is observed in latent heat of long-chain carboxylic acids (see, for example, T. Hasl, I. Jiricek, "The prediction of heat storage properties by the study of structural effect on organic phase change materials," Energy Procedia Vol. 46 (2014) pp. 301-309.). As can be seen from these examples, the odd-even effect on latent heat differs depending on the type of compound, making it difficult to predict with certainty.

[0023] [Compound represented by formula (I)] The latent heat storage material of the present disclosure contains a compound represented by the following formula (I):

[0024] [ka]

[0025] In formula (I), when n=m, n is an odd number. n is preferably an odd number from 5 to 17, more preferably an odd number from 5 to 15, even more preferably an odd number from 5 to 13, and particularly preferably an odd number from 7 to 13. In formula (I), when n = m, the amount of latent heat tends to be larger if n is an odd number of 5 or more. Also, in formula (I), when n = m, when n is an odd number of 5 to 17, a phase transition (also referred to as a "phase change") tends to occur easily in the optimum temperature range for using the latent heat storage material (for example, 25°C to 60°C).

[0026] In formula (I), when n≠m, n and m each independently represent an integer of 6 to 24, preferably an integer of 6 to 22, more preferably an integer of 6 to 20, even more preferably an integer of 6 to 18, still more preferably an integer of 6 to 16, and particularly preferably an integer of 7 to 14. In formula (I), when n≠m, the quantity of latent heat tends to be larger if n and m are each independently an integer of 6 or greater. Furthermore, in formula (I), when n≠m, and n and m are each independently an integer of 6 to 24, a phase transition (also referred to as a "phase change") tends to occur more easily in the optimum temperature range for using the latent heat storage material (for example, 25°C to 60°C).

[0027] In formula (I), X - represents an anion. X - The anion represented by is not particularly limited, and for example, nitrate ion (NO3 - ), chlorate ion (ClO3 - ), fluorine ion (F - ), chloride ions (Cl - ), bromide ion (Br - ), iodine ion (I - ), hydrogen sulfate ion (HSO4 - ), perchlorate ion (ClO4 - ), dihydrogen phosphate ion (H2PO4 - ), trifluoromethanesulfonate ion (CF3SO3 -), bis(trifluoromethanesulfonyl)imide ion [(CF3SO)2N - ], tetrafluoroborate ion (BF4 - ), hexafluorophosphate ion (PF6 - ), trifluoroacetate ion (CF3COO - ), and acetate ion (CH3COO - ) are listed. X - preferably represents a nitrate ion or a chlorate ion, and more preferably represents a nitrate ion.

[0028] The latent heat storage material of the present disclosure may contain only one type of compound represented by formula (I), or may contain two or more types.

[0029] The content of the compound represented by formula (I) in the latent heat storage material of the present disclosure is not particularly limited, but is, for example, preferably 30% by mass to 100% by mass, more preferably 50% by mass to 100% by mass, and even more preferably 70% by mass to 100% by mass, relative to the total solid content in the latent heat storage material. In the present disclosure, "total solid content in the latent heat storage material" means the total mass of the latent heat storage material when the latent heat storage material does not contain a solvent, and means the mass of the residue after removing the solvent from the latent heat storage material when the latent heat storage material contains a solvent. In this disclosure, "solvent" means water and organic solvents.

[0030] [Method for synthesizing the compound represented by formula (I)] The method for synthesizing the compound represented by formula (I) is not particularly limited. The compound represented by formula (I) can be synthesized by a known method. Specifically, the compound represented by formula (I) can be synthesized by the method described in the Examples.

[0031] The compound represented by formula (I) can be synthesized, for example, according to the method described in the aforementioned document [S. Steinert, W. Voigt, R. Glausch, M. Neuschutz, "Thermal characteristics of solid-solid phase transitions in long-chain dialkyl ammonium salts" Thermochimica Acta vol. 435 (2005) pp. 28-33.]. The synthesis method described in this document is incorporated herein by reference.

[0032] 〔binder〕 The latent heat storage material of the present disclosure may contain a binder. Examples of binders include thermoplastic resins and thermosetting resins. Examples of thermoplastic resins include acrylic resin, polyacetal, polyamide, polyethylene, polypropylene, polyethylene terephthalate, polybutylene terephthalate, polycarbonate, polystyrene, polyphenylene sulfide, polyvinyl chloride, ABS (acrylonitrile butadiene styrene) resin, and AS (acrylonitrile styrene) resin. Examples of thermosetting resins include phenolic resins, epoxy resins, melamine resins, urea resins, unsaturated polyesters, diallyl phthalate resins, urethane resins, and silicone resins.

[0033] The binder may be, for example, rubber. Examples of rubber include butadiene rubber, isoprene rubber, chloroprene rubber, halogenated butyl rubber, fluororubber, urethane rubber, acrylic rubber (ACM) obtained by copolymerizing an acrylic acid ester with another monomer, ethylene-propylene rubber obtained by coordination polymerization of ethylene and propylene using a Ziegler catalyst, butyl rubber (IIR) obtained by copolymerizing isobutylene and isoprene, styrene-butadiene rubber (SBR) obtained by copolymerizing butadiene and styrene, acrylonitrile-butadiene rubber (NBR) obtained by copolymerizing acrylonitrile and butadiene, and silicone rubber.

[0034] Furthermore, examples of binders include thermoplastic elastomers (TPE). Examples of thermoplastic elastomers include olefin-based thermoplastic elastomers (TPO), styrene-based thermoplastic elastomers (TPS), amide-based thermoplastic elastomers (TPA), and polyester-based thermoplastic elastomers (TPC).

[0035] When the latent heat storage material of the present disclosure contains a binder, it may contain only one type of binder or two or more types of binder.

[0036] When the latent heat storage material of the present disclosure contains a binder, the content of the binder is not particularly limited, but is, for example, preferably 50% by mass to 95% by mass, more preferably 60% by mass to 95% by mass, and even more preferably 70% by mass to 90% by mass, relative to the total solid content in the latent heat storage material.

[0037] [Other ingredients] The latent heat storage material of the present disclosure may contain components other than the components already described (so-called other components) as needed, within the range that does not impair the effects of the material. Examples of other components include various additives such as dispersants, dispersion aids, antifungal agents, antistatic agents, antioxidants, binders, thermally conductive materials, and flame retardants. One additive may have two or more functions. When the latent heat storage material of the present disclosure contains rubber as a binder, it may contain, in addition to rubber, a vulcanizing agent, a vulcanization aid, a softener, a plasticizer, and the like. Vulcanizing agents include, for example, sulfur, organic sulfur compounds, and metal oxides.

[0038] When the latent heat storage material of the present disclosure contains other components, the content of the other components can be set appropriately within a range that does not impair the effects of the latent heat storage material of the present disclosure.

[0039] <<Phase change temperature and latent heat>> The phase change temperature of the latent heat storage material of the present disclosure is 60°C or less, preferably 55°C or less, more preferably 50°C or less, and even more preferably 45°C or less. When the phase change temperature of the latent heat storage material of the present disclosure is 60°C or less, there is a tendency that deterioration in the performance of products to which the latent heat storage material is applied (for example, products such as electronic devices and batteries) can be effectively suppressed. The lower limit of the phase change temperature of the latent heat storage material of the present disclosure is not particularly limited, but is preferably, for example, 15°C or higher, more preferably 20°C or higher, and even more preferably 25°C or higher.

[0040] The latent heat quantity of the latent heat storage material of the present disclosure is not particularly limited, but is preferably, for example, 90 J / g or more, more preferably 100 J / g or more, even more preferably 110 J / g or more, and particularly preferably 120 J / g or more. The higher the latent heat quantity of the latent heat storage material of the present disclosure, the better, and there is no particular upper limit.

[0041] The phase change temperature of the latent heat storage material of the present disclosure is the temperature of the endothermic peak during temperature rise measured under the following conditions using a differential scanning calorimeter (DSC) as a measuring device. The latent heat quantity of the latent heat storage material of the present disclosure is the heat quantity of the endothermic peak during temperature rise measured under the following conditions using a differential scanning calorimeter as a measuring device. As the differential scanning calorimeter, for example, a differential scanning calorimeter (model: DSC3200) manufactured by Mac Science Co., Ltd. can be suitably used, but the differential scanning calorimeter is not limited to this.

[0042] -conditions- Measurement temperature range: 30℃~100℃ Heating rate: 10℃ / min Atmospheric gas: Air Measurement sample amount: 6.0 mg

[0043] <Applications of latent heat storage materials> The use of the latent heat storage material of the present disclosure is not particularly limited. The latent heat storage material of the present disclosure is a latent heat storage material that utilizes latent heat accompanying a phase change from solid to solid, and has a low phase change temperature of 60°C or less, a large amount of latent heat, and has repeatability, making it suitable as a latent heat storage material for use in electronic devices or power storage devices. Specific examples of the electronic device and the power storage device will be described later, and therefore will not be described here.

[0044] The latent heat storage material of the present disclosure utilizes the latent heat associated with a solid-to-solid phase change. Therefore, unlike conventional PCMs (e.g., compounds such as paraffin, sodium acetate trihydrate, erythritol, and 1-hexadecyl-3-methylimidazolium chloride) that utilize the latent heat of fusion associated with a solid-to-liquid phase change, the material does not melt into a liquid, eliminating the risk of leakage. Furthermore, the latent heat storage material of the present disclosure has a low phase change temperature of 60°C or less, a large amount of latent heat, and cycle characteristics, allowing the performance, lifespan, and safety of electronic devices and power storage devices to be maintained over a long period of time. The latent heat storage material of the present disclosure is particularly suitable as a latent heat storage material for use in high-output, high-capacity power storage devices that generate large amounts of heat at high temperatures.

[0045] [Latent heat storage material] The latent heat storage medium of the present disclosure includes the latent heat storage material of the present disclosure. The latent heat storage medium of the present disclosure contains the latent heat storage material of the present disclosure, and therefore has a low phase change temperature of 60°C or less, a large amount of latent heat, and repeatability.

[0046] The shape of the latent heat storage material of the present disclosure is not particularly limited and can be appropriately set depending on the purpose. The latent heat storage material of the present disclosure may have a planar shape or a three-dimensional shape. Examples of the planar shape include a sheet shape and a film shape. The three-dimensional shape is not particularly limited, and can be appropriately set depending on, for example, the shape of the target to which the latent heat storage material of the present disclosure is applied.

[0047] The method for producing the latent heat storage material of the present disclosure is not particularly limited. The latent heat storage medium of the present disclosure can be produced, for example, by a known method using the latent heat storage material of the present disclosure and a solvent.

[0048] The latent heat storage material of the present disclosure can be produced, for example, by the following method X.

[0049] (Method X) A latent heat storage material-forming composition containing a latent heat storage material of the present disclosure, which contains a compound represented by formula (I) and a binder, and a solvent, is applied to a temporary support to form a coating film of the latent heat storage material-forming composition. The coating film of the latent heat storage material-forming composition is then dried to form a latent heat storage material on the temporary support. The temporary support is then peeled off from the latent heat storage material, thereby producing a planar latent heat storage material.

[0050] The solvent in Method X is not particularly limited, and examples thereof include water, an organic solvent, or a mixed solvent of water and an organic solvent. Examples of organic solvents include alcohol-based solvents (e.g., methanol, ethanol, n-propanol, and i-propanol), ketone-based solvents (e.g., acetone, methyl ethyl ketone, and cyclohexanone), chlorine-based solvents (e.g., chloroform and dichloromethane), tetrahydrofuran, acetonitrile, ethyl acetate, and toluene.

[0051] The content of the solvent in the latent heat storage material forming composition is not particularly limited, and can be appropriately set depending on, for example, the types and amounts of components blended in the latent heat storage material forming composition.

[0052] In the composition for forming a latent heat storage material, the compound represented by formula (I) and the binder may simply be mixed together. The method for mixing the compound represented by formula (I) and the binder is not particularly limited, and examples thereof include a method in which they are mixed by stirring. The stirring means is not particularly limited, and a general stirring device can be used. Examples of the stirring device include mixers such as a paddle mixer and an impeller mixer. The stirring time is not particularly limited and can be set appropriately depending on the type of stirring device, the composition of the latent heat storage material-forming composition, and the like.

[0053] The temporary support is not particularly limited. Examples of the temporary support include a metal plate, a glass plate, a resin sheet, and various films. The surface of the resin sheet is preferably subjected to a release treatment.

[0054] The size of the temporary support is not particularly limited, and can be set appropriately depending on the size of the latent heat storage medium, for example. The thickness of the temporary support is not particularly limited, and may be appropriately set in consideration of, for example, workability.

[0055] The method for applying the latent heat storage material-forming composition onto the temporary support is not particularly limited, and examples thereof include methods using a die coater, a knife coater, an applicator, or the like.

[0056] The method for drying the coating film of the latent heat storage material-forming composition is not particularly limited, and examples thereof include a method using a heating device such as an oven. The drying temperature and drying time are not particularly limited as long as they can volatilize the solvent contained in the coating film of the latent heat storage material-forming composition.

[0057] The latent heat storage material of the present disclosure can be produced by the following method Y, for example, in addition to the above method X.

[0058] (Method Y) A mixture containing the latent heat storage material of the present disclosure, which contains the compound represented by formula (I) and a binder, and optionally a solvent, is kneaded using a kneader while being heated to obtain a kneaded mixture. The kneaded mixture is then molded to produce the latent heat storage medium of the present disclosure.

[0059] The solvent in Method Y has the same meaning as the solvent in Method X.

[0060] When the mixture contains a solvent, the content of the solvent in the mixture is not particularly limited and can be set appropriately depending on, for example, the types and amounts of the components blended in the mixture.

[0061] In the mixture, the compound represented by formula (I) and the binder may simply be mixed together. The method for mixing the compound represented by formula (I) and the binder is not particularly limited, and examples thereof include a method in which they are mixed by stirring. The stirring means is not particularly limited, and a general stirring device can be used. Examples of the stirring device include mixers such as a paddle mixer and an impeller mixer. The stirring time is not particularly limited and can be set appropriately depending on the type of stirring device, the composition of the mixture, and the like.

[0062] The heating temperature of the mixture is not particularly limited and can be set appropriately depending on, for example, the type of binder. The heating temperature is preferably a temperature at which the binder can be melted, and can be, for example, 170°C to 200°C.

[0063] The kneading means is not particularly limited, and a general kneading device can be used. Examples of the kneading device include a mixer, a two-roll mill, and a kneader. The kneading conditions are not particularly limited and can be appropriately set depending on the type of kneading device, the composition of the mixture, and the like.

[0064] Examples of molding processes include press molding, extrusion molding, injection molding, in-mold molding, and molding using a three-dimensional modeling machine. The molding conditions are not particularly limited and can be set appropriately depending on, for example, the type of molding device, the composition of the mixture, and the size of the latent heat storage medium.

[0065] [Electronic Devices] The electronic device of the present disclosure comprises the latent heat storage material of the present disclosure, and may comprise a latent heat storage body containing the latent heat storage material of the present disclosure (i.e., the latent heat storage body of the present disclosure). The electronic device of the present disclosure includes the latent heat storage material of the present disclosure, and therefore does not suffer from the problem of leakage due to melting.Furthermore, the electronic device of the present disclosure includes the latent heat storage material of the present disclosure, and therefore the characteristics, lifespan, and safety of the electronic device can be maintained for a long period of time. Examples of electronic devices according to the present disclosure include semiconductor devices such as integrated circuits (ICs) and IC modules, and light emitting diode (LED) devices.

[0066] The electronic device of the present disclosure may include the latent heat storage material of the present disclosure in any manner. In an embodiment where the electronic device of the present disclosure is, for example, a semiconductor device, a planar (e.g., sheet-shaped) latent heat storage material of the present disclosure (i.e., a latent heat storage material containing the latent heat storage material of the present disclosure) is disposed between the semiconductor device and a heat sink. According to such an embodiment, the heat generated in the semiconductor device is absorbed as latent heat by the compound represented by formula (I) contained in the latent heat storage material of the present disclosure, and the compound represented by formula (I) undergoes a phase change. During the phase change, the temperature is maintained constant, so the semiconductor device can be maintained at a constant temperature. The heat stored by the compound represented by formula (I) is transported and dissipated, for example, by a heat sink.

[0067] [Energy storage devices] The power storage device of the present disclosure includes the latent heat storage material of the present disclosure, and may include a latent heat storage body containing the latent heat storage material of the present disclosure (i.e., the latent heat storage body of the present disclosure). The power storage device of the present disclosure includes the latent heat storage material of the present disclosure, and therefore does not suffer from the problem of leakage due to melting. Furthermore, the power storage device of the present disclosure includes the latent heat storage material of the present disclosure, and therefore the characteristics, lifespan, and safety of the power storage device can be maintained for a long period of time. An example of the power storage device of the present disclosure is a battery. Examples of the battery include a lead-acid battery, an alkaline battery, a nickel-cadmium battery, a lithium-ion battery, and an all-solid-state battery.

[0068] The aspect in which the electricity storage device of the present disclosure includes the latent heat storage material of the present disclosure is not particularly limited. When the power storage device of the present disclosure is, for example, a battery, an example of an embodiment is one in which a three-dimensional latent heat storage material of the present disclosure (i.e., a latent heat storage material including the latent heat storage material of the present disclosure) is arranged between battery cells and / or between the battery cells and a heat sink so as to cover all or part of the battery cells. According to such an embodiment, the heat generated in the battery cells is absorbed as latent heat by the compound represented by formula (I) included in the latent heat storage material of the present disclosure, and the compound represented by formula (I) undergoes a phase change. Since the temperature is maintained constant during the phase change, the inside of the battery module can be maintained at a constant temperature. The heat stored by the compound represented by formula (I) is transported and dissipated, for example, by a heat sink. [Example]

[0069] The latent heat storage material of the present disclosure will be described in more detail below with reference to examples. The present disclosure is not limited to the following examples as long as it does not deviate from the gist of the disclosure.

[0070] The nuclear magnetic resonance (NMR) spectrum of each compound was measured using a Varian nuclear magnetic resonance spectrometer (model: UNITY INOVA 500 (500 MHz)). The infrared absorption spectrum of each compound was measured using a JASCO Fourier transform infrared spectrophotometer (model: FT / IR-400). The elemental analysis of each compound was performed using a PerkinElmer fully automated elemental analyzer (CHNS / O) (model: 2400II series).

[0071] [Synthesis of dialkylammonium nitrates] [Synthesis Example 1] Compound 1: Diheptylammonium nitrate ((CH 15 )2N + H2NO3 - 〕 To a solution of diheptylamine dissolved in isopropanol, a solution of concentrated nitric acid dissolved in isopropanol was added little by little until the whole became slightly acidic. The resulting solution was cooled to 10°C and filtered to obtain colorless crystals. The obtained crystals were recrystallized twice using a mixed solvent of n-hexane and ethanol to obtain the target compound (Compound 1: diheptylammonium nitrate).

[0072] The obtained compound 1 1 The results of the H-NMR spectrum and the infrared absorption spectrum by Fourier transform infrared spectroscopy (FT-IR) are shown below. 1 H-NMR (500MHz, CDCl3) δ(ppm): 8.766 (2H brs), 3.010-2.970 (4H m), 1.711 (4H quintet / J=7.6Hz), 1.322-1.204 (m, 16H), 0.875 (6H t / J=7.0Hz) FT-IR νmax (cm -1 ): 3014, 2958, 2918, 2853, 1624, 1470, 1350

[0073] The results of elemental analysis of the obtained Compound 1 are shown below. Calculated value (%) (C14 H 32 N2O3): C, 60.83; H, 11.67; N, 10.13 Measured values ​​(%): C, 60.97; H, 11.77; N, 10.30

[0074] [Synthesis Example 2] Compound 2: Dinonylammonium nitrate ((CH 19 )2N + H2NO3 - 〕 A solution of nonylamine and 1.5 times the molar amount of triethylamine dissolved in chloroform was added dropwise to the solution of nonylamine and nonanoic acid chloride dissolved in chloroform using a dropping funnel. After the dropwise addition was completed, the resulting chloroform solution was stirred at room temperature for 1 hour and then heated under reflux for 2 hours. The chloroform solution after heating under reflux was cooled to room temperature and washed with water. Next, anhydrous sodium sulfate was added to the chloroform layer to remove moisture, and the solvent was removed to obtain colorless crystals. The resulting crystals were recrystallized using a mixed solvent of chloroform and n-hexane to give N-nonylnonanamide (CH 17 CONHC9H 19 ) was obtained. The N-nonylnonanamide obtained above and lithium aluminum hydride (LiAlH4) were added to anhydrous diethyl ether, and the mixture was refluxed for 2 hours, followed by a reaction at room temperature for 2 hours. After the reaction was completed, water was added to the obtained solution to decompose the excess lithium aluminum hydride. Next, anhydrous sodium sulfate was added to the diethyl ether layer to remove water, and the solvent was then removed to obtain crystals. The obtained crystals were recrystallized twice using n-hexane to obtain dinonylamine. Next, a solution of concentrated nitric acid dissolved in isopropanol was added little by little to a solution of dinonylamine dissolved in isopropanol until the whole became slightly acidic. The obtained solution was cooled to 10°C and filtered to obtain colorless crystals. The obtained crystals were recrystallized twice using a mixed solvent of chloroform and n-hexane to obtain the target compound (Compound 2: dinonylammonium nitrate).

[0075] The obtained compound 2 1 The results of the H-NMR spectrum and the infrared absorption spectrum by Fourier transform infrared spectroscopy (FT-IR) are shown below. 1 H NMR (500MHz, CDCl3) δ(ppm): 8.742 (2H brs), 2.987-2.956 (4H m), 1.696 (4H quintet / J=7.6Hz), 1.350-1.190 (m, 24H), 0.865 (6H t / J=7.0Hz) FT-IR νmax (cm -1 ): 3015, 2957, 2919, 2853, 1624, 1470, 1350

[0076] The results of elemental analysis of the obtained compound 2 are shown below. Calculated value (%) (C 18 H 40 N2O3): C, 65.02; H, 12.13; N, 8.42 Measurements (%): C, 64.85; H, 12.22; N, 8.37

[0077] [Synthesis Example 3] Compound 3: Diundecylammonium nitrate (C 11 H 23 )2N + H2NO3 - 〕 A solution of undecylamine and 1.5 times the molar amount of triethylamine dissolved in chloroform was added dropwise to the solution of undecylamine and an equimolar amount of undecanoic acid chloride dissolved in chloroform using a dropping funnel. After the dropwise addition was completed, the resulting chloroform solution was stirred at room temperature for 1 hour and then heated under reflux for 2 hours. The chloroform solution after heating under reflux was cooled to room temperature and washed with water. Anhydrous sodium sulfate was then added to the chloroform layer to remove moisture, and the solvent was then removed to obtain colorless crystals. The resulting crystals were recrystallized using a mixed solvent of chloroform and n-hexane to obtain N-undecylundecaneamide (C 10 H 21 CONHC11 H 23 ) was obtained. The N-undecylundecaneamide obtained above and lithium aluminum hydride (LiAlH4) were added to anhydrous diethyl ether, and the mixture was refluxed for 2 hours, followed by a reaction at room temperature for 2 hours. After the reaction was completed, water was added to the obtained solution to decompose the excess lithium aluminum hydride. Next, anhydrous sodium sulfate was added to the diethyl ether layer to remove water, and the solvent was then removed to obtain crystals. The obtained crystals were recrystallized twice using n-hexane to obtain diundecylamine. Next, a solution of concentrated nitric acid dissolved in isopropanol was added little by little to a solution of diundecylamine dissolved in isopropanol until the whole solution became slightly acidic. The obtained solution was cooled to 10°C and filtered to obtain colorless crystals. The obtained crystals were recrystallized twice using a mixed solvent of chloroform and n-hexane to obtain the target compound (Compound 3: diundecylammonium nitrate).

[0078] The obtained compound 3 1 The results of the H-NMR spectrum and the infrared absorption spectrum by Fourier transform infrared spectroscopy (FT-IR) are shown below. 1 H NMR (500MHz, CDCl3) δ(ppm): 8.805 (2H brs), 3.010-2.930 (4H m), 1.727 (4H quintet / J=7.8Hz), 1.360-1.204 (32H, m), 0.874 (6H t / J=7.0Hz) FT-IR νmax (cm -1 ): 3014, 2957, 2917, 2853, 1624, 1471, 1353

[0079] The results of elemental analysis of the obtained compound 3 are shown below. Calculated value (%) (C 22 H 48 N2O3) : C, 67.99; H, 12.45; N, 7.21 Measurements (%): C, 68.13; H, 12.66; N, 6.87

[0080] [Synthesis Example 4] Compound 4: Ditridecylammonium nitrate [(C 13 H 27 )2N + H2NO3 - 〕 A solution of tridecylamine and triethylamine in an amount 1.5 times the molar amount of the tridecylamine dissolved in chloroform was added dropwise using a dropping funnel. After the dropwise addition, the resulting chloroform solution was stirred at room temperature for 1 hour and then heated under reflux for 2 hours. The chloroform solution after heating under reflux was cooled to room temperature and washed with water. Anhydrous sodium sulfate was then added to the chloroform layer to remove moisture, and the solvent was then removed to obtain colorless crystals. The resulting crystals were recrystallized using a mixed solvent of chloroform and n-hexane to obtain N-tridecyltridecanamide (C 12 H 25 CONHC 13 H 27 ) was obtained. The N-tridecyltridecanamide obtained above and lithium aluminum hydride (LiAlH4) were added to anhydrous diethyl ether, and the mixture was refluxed for 2 hours, followed by a reaction at room temperature for 2 hours. After the reaction was completed, water was added to the obtained solution to decompose the excess lithium aluminum hydride. Next, anhydrous sodium sulfate was added to the diethyl ether layer to remove water, and the solvent was then removed to obtain crystals. The obtained crystals were recrystallized twice using n-hexane to obtain ditridecylamine. Next, a solution of concentrated nitric acid dissolved in isopropanol was added little by little to a solution of ditridecylamine dissolved in isopropanol until the whole became slightly acidic. The obtained solution was cooled to 10°C and filtered to obtain colorless crystals. The obtained crystals were recrystallized twice using a mixed solvent of chloroform and n-hexane to obtain the target compound (Compound 4: ditridecylammonium nitrate).

[0081] The obtained compound 4 1The results of the H-NMR spectrum and the infrared absorption spectrum by Fourier transform infrared spectroscopy (FT-IR) are shown below. 1 H NMR (500MHz, CDCl3) δ(ppm): 8.760 (2H brs), 3.020-2.970 (4H m), 1.725 (4H quintet / J=7.6Hz), 1.350-1.200 (m, 40H), 0.875 (6H t / J=7.0Hz) FT-IR νmax (cm -1 ): 3015, 2958, 2919, 2853, 1624, 1470, 1351

[0082] The results of elemental analysis of the obtained compound 4 are shown below. Calculated value (%) (C 26 H 56 N2O3) : C, 70.22; H, 12.69; N, 6.30 Measured values ​​(%): C, 70.34; H, 12.80; N, 6.40

[0083] [Synthesis Example 5] Compound 5: Heptyldecylammonium nitrate [C7H 15 (C 10 H 21 )N + H2NO3 - 〕 A solution of heptylamine and 1.5 times the molar amount of triethylamine dissolved in chloroform was added dropwise to a solution of decanoic acid chloride dissolved in chloroform using a dropping funnel. After the dropwise addition, the resulting chloroform solution was stirred at room temperature for 1 hour and then heated under reflux for 2 hours. The chloroform solution after heating under reflux was cooled to room temperature and washed with water. Anhydrous sodium sulfate was then added to the chloroform layer to remove moisture, and the solvent was then removed to obtain colorless crystals. The resulting crystals were recrystallized using n-hexane to give N-heptyldecanoic acid amide (CH 19 CONHC7H 15) was obtained. The N-heptyldecanoic acid amide obtained above and lithium aluminum hydride (LiAlH4) were added to anhydrous diethyl ether, and the mixture was refluxed for 2 hours, followed by a reaction at room temperature for 2 hours. After the reaction was completed, water was added to the obtained solution to decompose the excess lithium aluminum hydride. Next, anhydrous sodium sulfate was added to the diethyl ether layer to remove water, and the solvent was then removed to obtain crystals. The obtained crystals were recrystallized twice using n-hexane to obtain heptyldecylamine. Next, a solution of concentrated nitric acid dissolved in isopropanol was added little by little to a solution of heptyldecylamine dissolved in isopropanol until the whole became slightly acidic. The obtained solution was cooled to 10°C and filtered to obtain colorless crystals. The obtained crystals were recrystallized twice using a mixed solvent of chloroform and n-hexane to obtain the target compound (Compound 5: heptyldecylammonium nitrate).

[0084] The obtained compound 5 1 The results of the H-NMR spectrum and the infrared absorption spectrum by Fourier transform infrared spectroscopy (FT-IR) are shown below. 1 H NMR (500MHz, CDCl3) δ(ppm): 8.773 (2H brs), 2.983 (4H quintet / J=7.0Hz), 1.703 (4H quintet / J=7.4Hz), 1.370-1.200 (m, 22H), 0.868 (3H t / J=7.0Hz), 0.862(3H t / J=7.0Hz) FT-IR νmax (cm -1 ): 2956, 2853, 1637, 1472, 1354

[0085] The results of elemental analysis of the obtained compound 5 are shown below. Calculated value (%) (C 17 H 38 N2O3): C, 64.11; H, 12.03; N, 8.80 Measurements (%): C, 64.53; H, 12.25; N, 8.68

[0086] [Synthesis Example 6] Compound 6: Octyldecylammonium nitrate [C8H 17 (C 10 H 21 )N + H2NO3 - 〕 A solution of octylamine and 1.5 times the molar amount of triethylamine dissolved in chloroform was added dropwise to the solution of decanoic acid chloride dissolved in chloroform using a dropping funnel. After the dropwise addition, the resulting chloroform solution was stirred at room temperature for 1 hour and then heated under reflux for 2 hours. The chloroform solution after heating under reflux was cooled to room temperature and washed with water. Anhydrous sodium sulfate was then added to the chloroform layer to remove water, and the solvent was then removed to obtain colorless crystals. The resulting crystals were recrystallized using n-hexane to give N-octyldecanamide (CH 19 CONHC8H 17 ) was obtained. The N-octyldecanamide obtained above and lithium aluminum hydride (LiAlH4) were added to anhydrous diethyl ether, and the mixture was refluxed for 2 hours, followed by a reaction at room temperature for 2 hours. After the reaction was completed, water was added to the obtained solution to decompose the excess lithium aluminum hydride. Next, anhydrous sodium sulfate was added to the diethyl ether layer to remove water, and the solvent was then removed to obtain crystals. The obtained crystals were recrystallized twice using n-hexane to obtain octyldecylamine. Next, a solution of concentrated nitric acid dissolved in isopropanol was added little by little to a solution of octyldecylamine dissolved in isopropanol until the whole solution became slightly acidic. The obtained solution was cooled to 10°C and filtered to obtain colorless crystals. The obtained crystals were recrystallized twice using a mixed solvent of chloroform and n-hexane to obtain the target compound (Compound 6: octyldecylammonium nitrate).

[0087] The obtained compound 6 1 The results of the H-NMR spectrum and the infrared absorption spectrum by Fourier transform infrared spectroscopy (FT-IR) are shown below. 1H NMR (500MHz, CDCl3) δ(ppm): 8.708 (2H brs), 3.010-2.960 (4H m), 1.710 (4H quintet / J=7.2Hz), 1.360-1.200 (m, 24H), 0.871 (3H t / J=7.0Hz), 0.864(3Ht / J=7.0Hz) FT-IR νmax (cm -1 ): 2956, 2853, 1635, 1470, 1354

[0088] The results of elemental analysis of the obtained compound 6 are shown below. Calculated value (%) (C 18 H 40 N2O3): C, 65.02; H, 12.13; N, 8.42 Measurements (%): C, 64.47; H, 12.13; N, 8.45

[0089] [Synthesis Example 7] Compound 7: Nonyldecylammonium nitrate [C9H 19 (C 10 H 21 )N + H2NO3 - 〕 A solution of nonylamine and 1.5 times the molar amount of triethylamine dissolved in chloroform was added dropwise to the solution of decanoic acid chloride dissolved in chloroform using a dropping funnel. After the dropwise addition, the resulting chloroform solution was stirred at room temperature for 1 hour and then heated under reflux for 2 hours. The chloroform solution after heating under reflux was cooled to room temperature and washed with water. Anhydrous sodium sulfate was then added to the chloroform layer to remove water, and the solvent was then removed to obtain colorless crystals. The resulting crystals were recrystallized using n-hexane to give N-nonyldecanamide (CH 19 CONHC9H 19) was obtained. The N-nonyldecanamide obtained above and lithium aluminum hydride (LiAlH4) were added to anhydrous diethyl ether, and the mixture was refluxed for 2 hours, followed by a reaction at room temperature for 2 hours. After the reaction was completed, water was added to the resulting solution to decompose the excess lithium aluminum hydride. Next, anhydrous sodium sulfate was added to the diethyl ether layer to remove water, and the solvent was then removed to obtain crystals. The resulting crystals were recrystallized twice using n-hexane to obtain nonyldecylamine. Next, a solution of concentrated nitric acid dissolved in isopropanol was added little by little to a solution of nonyldecylamine dissolved in isopropanol until the entire mixture became slightly acidic. The resulting solution was cooled to 10°C and filtered to obtain colorless crystals. The resulting crystals were recrystallized twice using a mixed solvent of chloroform and n-hexane to obtain the target compound (Compound 7: nonyldecylammonium nitrate).

[0090] The obtained compound 7 1 The results of the H-NMR spectrum and the infrared absorption spectrum by Fourier transform infrared spectroscopy (FT-IR) are shown below. 1 H NMR (500MHz, CDCl3) δ(ppm): 8.760 (2H brs), 3.100-2.970 (4H m), 1.703 (4H quintet / J=7.0Hz), 1.360-1.200 (m, 26H), 0.872 (3H t / J=7.0Hz), 0.865(3Ht / J=7.0Hz) FT-IR νmax (cm -1 ): 2957, 2853, 1637, 1470, 1355

[0091] The results of elemental analysis of the obtained compound 7 are shown below. Calculated value (%) (C 19 H 42 N2O3): C, 65.84; H, 12.22; N, 8.08 Measured values ​​(%): C, 64.72; H, 12.21; N, 8.08

[0092] [Synthesis Example 8] Compound 8: Heptyldodecylammonium nitrate [C7H 15 (C 12 H 25 )N + H2NO3 - 〕 A solution of heptylamine and 1.5 times the molar amount of triethylamine dissolved in chloroform was added dropwise to the solution of dodecanoic acid chloride dissolved in chloroform using a dropping funnel. After the dropwise addition, the resulting chloroform solution was stirred at room temperature for 1 hour and then heated under reflux for 2 hours. The chloroform solution after heating under reflux was cooled to room temperature and washed with water. Anhydrous sodium sulfate was then added to the chloroform layer to remove moisture, and the solvent was then removed to obtain colorless crystals. The resulting crystals were recrystallized using n-hexane to give N-heptyldodecanamide (C 11 H 23 CONHC7H 15 ) was obtained. The N-heptyldodecanamide obtained above and lithium aluminum hydride (LiAlH4) were added to anhydrous diethyl ether, and the mixture was refluxed for 2 hours, followed by a reaction at room temperature for 2 hours. After the reaction was completed, water was added to the obtained solution to decompose the excess lithium aluminum hydride. Next, anhydrous sodium sulfate was added to the diethyl ether layer to remove water, and the solvent was then removed to obtain crystals. The obtained crystals were recrystallized twice using n-hexane to obtain heptyldodecylamine. Next, a solution of concentrated nitric acid dissolved in isopropanol was added little by little to a solution of heptyldodecylamine dissolved in isopropanol until the whole solution became slightly acidic. The obtained solution was cooled to 10°C and filtered to obtain colorless crystals. The obtained crystals were recrystallized twice using a mixed solvent of chloroform and n-hexane to obtain the target compound (Compound 8: heptyldodecylammonium nitrate).

[0093] The obtained compound 8 1 The results of the H-NMR spectrum and the infrared absorption spectrum by Fourier transform infrared spectroscopy (FT-IR) are shown below. 1 H NMR (500MHz, CDCl3) δ(ppm): 8.697 (2H brs), 3.012-2.960 (4H m), 1.701 (4H quintet / J=7.1Hz), 1.370-1.200 (m, 26H), 0.872 (3H t / J=7.0Hz), 0.865 (3Ht / J=7.0Hz) FT-IR νmax (cm -1 ): 2957, 2852, 1636, 1470, 1354

[0094] The results of elemental analysis of the obtained compound 8 are shown below. Calculated value (%) (C 19 H 42 N2O3): C, 65.84; H, 12.22; N, 8.08 Measurements (%): C, 64.79; H, 13.19; N, 8.09

[0095] [Synthesis Example 9] Compound 9: Octyldodecylammonium nitrate [C8H 17 (C 12 H 25 )N + H2NO3 - 〕 A solution of octylamine and triethylamine in an amount 1.5 times the molar amount of the octylamine dissolved in chloroform was added dropwise using a dropping funnel. After the dropwise addition, the resulting chloroform solution was stirred at room temperature for 1 hour and then heated under reflux for 2 hours. The chloroform solution after heating under reflux was cooled to room temperature and washed with water. Anhydrous sodium sulfate was then added to the chloroform layer to remove moisture, and the solvent was then removed to obtain colorless crystals. The resulting crystals were recrystallized using n-hexane to give N-octyldodecanamide (C 11 H 23 CONHC8H 17) was obtained. The N-octyldodecanamide obtained above and lithium aluminum hydride (LiAlH4) were added to anhydrous diethyl ether, and the mixture was refluxed for 2 hours, followed by a reaction at room temperature for 2 hours. After the reaction was completed, water was added to the obtained solution to decompose the excess lithium aluminum hydride. Next, anhydrous sodium sulfate was added to the diethyl ether layer to remove water, and the solvent was then removed to obtain crystals. The obtained crystals were recrystallized twice using n-hexane to obtain octyldodecylamine. Next, a solution of concentrated nitric acid dissolved in isopropanol was added little by little to a solution of octyldodecylamine dissolved in isopropanol until the whole solution became slightly acidic. The obtained solution was cooled to 10°C and filtered to obtain colorless crystals. The obtained crystals were recrystallized twice using a mixed solvent of chloroform and n-hexane to obtain the target compound (Compound 9: octyldodecylammonium nitrate).

[0096] The obtained compound 9 1 The results of the H-NMR spectrum and the infrared absorption spectrum by Fourier transform infrared spectroscopy (FT-IR) are shown below. 1 H NMR (500MHz, CDCl3) δ(ppm): 8.766 (2H brs), 3.020-2.950 (4H m), 1.711(4H quintet / J=7.6Hz), 1.370-1.210 (m, 28H), 0.870 (6H t / J=7.0Hz), 0.864 (3Ht / J=7.0Hz) FT-IR νmax (cm -1 ): 2956, 2853, 1635, 1470, 1355

[0097] The results of elemental analysis of the obtained compound 9 are shown below. Calculated value (%) (C 20 H 44 N2O3): C, 66.62; H, 12.30; N, 7.77 Measurements (%): C, 66.60; H, 12.46; N, 7.79

[0098] [Synthesis Example 10] Compound 10: Nonyldodecylammonium nitrate [C9H 19 (C 12 H 25 )N + H2NO3 - 〕 A solution of nonylamine and triethylamine in a molar amount 1.5 times that of the nonylamine dissolved in chloroform was added dropwise using a dropping funnel to a solution of dodecanoic acid chloride in an equimolar amount to the nonylamine dissolved in chloroform. After the dropwise addition was completed, the resulting chloroform solution was stirred at room temperature for 1 hour and then heated under reflux for 2 hours. The chloroform solution after heating under reflux was cooled to room temperature and washed with water. Next, anhydrous sodium sulfate was added to the chloroform layer to remove water, and the solvent was removed to obtain colorless crystals. The resulting crystals were recrystallized using a mixed solvent of chloroform and n-hexane to obtain N-nonyldodecanamide (C 11 H 23 CONHC9H 19 ) was obtained. The N-nonylnonanamide obtained above and lithium aluminum hydride (LiAlH4) were added to anhydrous diethyl ether, and the mixture was refluxed for 2 hours, followed by a reaction at room temperature for 2 hours. After the reaction was completed, water was added to the obtained solution to decompose the excess lithium aluminum hydride. Next, anhydrous sodium sulfate was added to the diethyl ether layer to remove water, and then the solvent was removed to obtain crystals. The obtained crystals were recrystallized twice using n-hexane to obtain nonyldodecylamine. Next, a solution of concentrated nitric acid dissolved in isopropanol was added little by little to a solution of nonyldodecylamine dissolved in isopropanol until the whole became slightly acidic. The obtained solution was cooled to 10°C and filtered to obtain colorless crystals. The obtained crystals were recrystallized twice using a mixed solvent of chloroform and n-hexane to obtain the target compound (Compound 10: nonyldodecylammonium nitrate).

[0099] The obtained compound 10 1 The results of the H-NMR spectrum and the infrared absorption spectrum by Fourier transform infrared spectroscopy (FT-IR) are shown below. 1 H NMR (500MHz, CDCl3) δ(ppm): 8.675 (2H, brs), 3.010-2.950 (4H, m), 1.725 (4H, quintet / J=7.6Hz), 1.360-1.200 (m, 30H), 0.875(3H, t / J=7.0Hz), 0.871(3H, t / J=7.0Hz) FT-IR νmax (cm -1 ): 2957, 2853, 1637, 1470, 1353

[0100] The results of elemental analysis of the obtained compound 10 are shown below. Calculated value (%) (C 21 H 46 N2O3): C, 67.33; H, 12.38; N, 7.48 Measurements (%): C, 67.54 H, 12.45; N, 7.50

[0101] [Comparative Synthesis Example 1] Comparative compound 1: Dihexylammonium nitrate ((CH 13 )2N + H2NO3 - 〕 To a solution of dihexylamine dissolved in isopropanol, a solution of concentrated nitric acid dissolved in isopropanol was added little by little until the whole became slightly acidic. The resulting solution was cooled to 10°C and filtered to obtain colorless crystals. The obtained crystals were recrystallized twice using a mixed solvent of n-hexane and ethanol to obtain the target compound (comparative compound 1: dihexylammonium nitrate).

[0102] The obtained comparative compound 1 1 The results of the H-NMR spectrum and the infrared absorption spectrum by Fourier transform infrared spectroscopy (FT-IR) are shown below. 1H NMR (500MHz, CDCl3) δ(ppm): 8.782 (2H brs), 2.991 (4H quintet / J=7.5Hz), 1.704 (4H quintet / J=7.5Hz), 1.370-1.210 (m, 12H), 0.863 (6H t / J=7.0Hz) FT-IR νmax (cm -1 ): 3017, 2918, 2853, 1622, 1472, 1351

[0103] The results of elemental analysis of the obtained comparative compound 1 are shown below. Calculated value (%) (C 12 H 28 N2O3): C, 58.03; H, 11.36; N, 11.28 Measured values ​​(%): C, 58.03; H, 11.42; N, 11.38

[0104] [Comparative Synthesis Example 2] Comparative compound 2: Dioctylammonium nitrate ((C8H 17 )2N + H2NO3 - 〕 To a solution of dioctylamine dissolved in isopropanol, a solution of concentrated nitric acid dissolved in isopropanol was added little by little until the whole became slightly acidic. The resulting solution was cooled to 10°C and filtered to obtain colorless crystals. The obtained crystals were recrystallized twice using ethanol to obtain the target compound (comparative compound 2: dioctylammonium nitrate).

[0105] The obtained comparative compound 2 1 The results of the H-NMR spectrum and the infrared absorption spectrum by Fourier transform infrared spectroscopy (FT-IR) are shown below. 1H NMR (500MHz, CDCl3) δ(ppm): 8.748 (2H brs), 3.020-2.900 (4H m), 1.716 (4H quintet / J=7.6Hz), 1.370-1.100 (m, 20H), 0.873 (6H t / J=6.8Hz) FT-IR νmax (cm -1 ): 3018, 2917, 2853, 1623, 1472, 1351

[0106] The results of elemental analysis of the obtained comparative compound 2 are shown below. Calculated value (%) (C 16 H 36 N2O3): C, 63.12; H, 11.92; N, 9.20 Measurements (%): C, 63.37; H, 12.00; N, 9.28

[0107] Comparative Synthesis Example 3 Comparative compound 3: Didecylammonium nitrate [(C 10 H 21 )2N + H2NO3 - 〕 To a solution of didecylamine dissolved in isopropanol, a solution of concentrated nitric acid dissolved in isopropanol was added little by little until the whole became slightly acidic. The resulting solution was cooled to 10°C and filtered to obtain colorless crystals. The obtained crystals were recrystallized twice using ethanol to obtain the target compound (comparative compound 3: didecylammonium nitrate).

[0108] The obtained comparative compound 3 1 The results of the H-NMR spectrum and the infrared absorption spectrum by Fourier transform infrared spectroscopy (FT-IR) are shown below. 1H NMR (500MHz, CDCl3) δ(ppm): 8.774 (2H brs), 3.01-2.90 (4H m), 1.705 (4H quintet / J=7.0Hz), 1.350-1.170 (m, 28H), 0.874 (6H t / J=7.0Hz) FT-IR νmax (cm -1 ): 3010, 2918, 2853, 1624, 1472, 1353

[0109] The results of elemental analysis of the obtained comparative compound 3 are shown below. Calculated value (%) (C 20 H 44 N2O3): C, 66.62; H, 12.30; N, 7.77 Measurements (%): C, 66.94; H, 12.51; N, 7.84

[0110] Comparative Synthesis Example 4 Comparative compound 4: Didodecylammonium nitrate [(C 12 H 25 )2N + H2NO3 - 〕 A solution of concentrated nitric acid dissolved in isopropanol was added little by little to a solution of didodecylamine dissolved in isopropanol until the whole became slightly acidic. The resulting solution was cooled to 10°C and filtered to obtain colorless crystals. The obtained crystals were recrystallized twice using ethanol to obtain the target compound (comparative compound 4: didodecylammonium nitrate).

[0111] The obtained comparative compound 4 1 The results of the H-NMR spectrum and the infrared absorption spectrum by Fourier transform infrared spectroscopy (FT-IR) are shown below. 1 H NMR (500MHz, CDCl3) δ(ppm): 8.772 (2H brs), 3.00-2.91 (4H m), 1.75-1.63 (4H m), 1.40-1.10 (m, 36H), 0.863 (6H t / J=7.0Hz) FT-IR νmax (cm -1 ): 3011, 2919, 2852, 1623, 1470, 1351

[0112] The results of elemental analysis of the obtained comparative compound 4 are shown below. Calculated value (%) (C 24 H 52 N2O3): C, 69.18; H, 12.58; N, 6.72 Measurements (%): C, 69.49; H, 12.80; N, 6.74

[0113] Comparative Synthesis Example 5 Comparative compound 5: Ditetradecylammonium nitrate [(C 14 H 29 )2N + H2NO3 - 〕 A solution of tetradecylamine and triethylamine in an amount 1.5 times the molar amount of the tetradecylamine dissolved in chloroform was added dropwise using a dropping funnel. After the dropwise addition, the resulting chloroform solution was stirred at room temperature for 1 hour and then heated under reflux for 2 hours. The chloroform solution after heating under reflux was cooled to room temperature and washed with water. Anhydrous sodium sulfate was then added to the chloroform layer to remove moisture, and the solvent was then removed to obtain colorless crystals. The resulting crystals were recrystallized using a mixed solvent of chloroform and n-hexane to obtain N-tetradecyltetradecanamide (C 13 H 27 CONHC 14 H 29) was obtained. The N-tetradecyltetradecanamide obtained above and lithium aluminum hydride (LiAlH4) were added to anhydrous diethyl ether, and the mixture was refluxed for 2 hours, followed by a reaction at room temperature for 2 hours. After the reaction was completed, water was added to the obtained solution to decompose the excess lithium aluminum hydride. Next, anhydrous sodium sulfate was added to the diethyl ether layer to remove water, and the solvent was then removed to obtain crystals. The obtained crystals were recrystallized twice using n-hexane to obtain ditetradecylamine. Next, a solution of concentrated nitric acid dissolved in isopropanol was added little by little to a solution of ditetradecylamine dissolved in isopropanol until the whole solution became slightly acidic. The obtained solution was cooled to 10°C and filtered to obtain colorless crystals. The obtained crystals were recrystallized twice using ethanol to obtain the target compound (comparative compound 5: ditetradecylammonium nitrate).

[0114] The obtained comparative compound 5 1 The results of the H-NMR spectrum and the infrared absorption spectrum by Fourier transform infrared spectroscopy (FT-IR) are shown below. 1 H NMR (500MHz, CDCl3) δ(ppm): 8.766 (2H brs), 2.972 (4H m), 1.716 (4H quintet / J=7.6Hz), 1.322-1.204 (m, 44H), 0.875 (6H t / J=7.0Hz) FT-IR νmax (cm -1 ):3015, 2919, 2853, 1623, 1473, 1350

[0115] The results of elemental analysis of the obtained comparative compound 5 are shown below. Calculated value (%) (C 28 H 60 N2O3): C, 71.13; H, 12.79; N, 5.93 Measurements (%): C, 72.39; H, 13.20; N, 5.55

[0116] [Synthesis of dialkylammonium chlorate] [Synthesis Example 11] Compound 11: Dinonylammonium chlorate ((CH 19 )2N + H2ClO3 - 〕 A solution of nonylamine and 1.5 times the molar amount of triethylamine dissolved in chloroform was added dropwise to the solution of nonylamine and nonanoic acid chloride dissolved in chloroform using a dropping funnel. After the dropwise addition was completed, the resulting chloroform solution was stirred at room temperature for 1 hour and then heated under reflux for 2 hours. The chloroform solution after heating under reflux was cooled to room temperature and washed with water. Next, anhydrous sodium sulfate was added to the chloroform layer to remove moisture, and the solvent was removed to obtain colorless crystals. The resulting crystals were recrystallized using a mixed solvent of chloroform and n-hexane to give N-nonylnonanamide (CH 17 CONHC9H 19 ) was obtained. The N-nonylnonanamide obtained above and lithium aluminum hydride (LiAlH4) were added to anhydrous diethyl ether, and the mixture was refluxed for 2 hours, followed by a reaction at room temperature for 2 hours. After the reaction was completed, water was added to the obtained solution to decompose the excess lithium aluminum hydride. Next, anhydrous sodium sulfate was added to the diethyl ether layer to remove water, and the solvent was then removed to obtain crystals. The obtained crystals were recrystallized twice using n-hexane to obtain dinonylamine. Next, a solution of 60% by mass of chloric acid dissolved in isopropanol was added little by little to a solution of dinonylamine dissolved in isopropanol until the whole solution became slightly acidic. The obtained solution was cooled to 10°C and filtered to obtain colorless crystals. The obtained crystals were recrystallized twice using isopropanol to obtain the target compound (Compound 11: dinonylammonium chlorate).

[0117] The obtained compound 11 1 The results of the H-NMR spectrum are shown below. 1H NMR (500MHz, CDCl3) δ(ppm): 6.931 (2H brs), 3.070 (4H quintet / J=3.9Hz), 1.778 (4H quintet / J=7.6Hz), 1.390-1.210 (m, 24H), 0.874 (6H t / J=7.0Hz)

[0118] [Synthesis Example 12] Compound 12: Diundecylammonium chlorate [(C 11 H 23 )2N + H2ClO3 - 〕 A solution of undecylamine and 1.5 times the molar amount of triethylamine dissolved in chloroform was added dropwise to the solution of undecylamine and an equimolar amount of undecanoic acid chloride dissolved in chloroform using a dropping funnel. After the dropwise addition was completed, the resulting chloroform solution was stirred at room temperature for 1 hour and then heated under reflux for 2 hours. The chloroform solution after heating under reflux was cooled to room temperature and washed with water. Anhydrous sodium sulfate was then added to the chloroform layer to remove moisture, and the solvent was then removed to obtain colorless crystals. The resulting crystals were recrystallized using a mixed solvent of chloroform and n-hexane to obtain N-undecylundecaneamide (C 10 H 21 CONHC 11 H 23) was obtained. The N-undecylundecaneamide obtained above and lithium aluminum hydride (LiAlH4) were added to anhydrous diethyl ether, and the mixture was refluxed for 2 hours, followed by a reaction at room temperature for 2 hours. After the reaction was completed, water was added to the obtained solution to decompose the excess lithium aluminum hydride. Next, anhydrous sodium sulfate was added to the diethyl ether layer to remove water, and the solvent was then removed to obtain crystals. The obtained crystals were recrystallized twice using n-hexane to obtain diundecylamine. Next, a solution of 60% by mass of chloric acid dissolved in isopropanol was added little by little to a solution of diundecylamine dissolved in isopropanol until the whole became slightly acidic. The obtained solution was cooled to 10°C and filtered to obtain colorless crystals. The obtained crystals were recrystallized twice using isopropanol to obtain the target compound (Compound 12: diundecylammonium chlorate).

[0119] The obtained compound 12 1 The results of the H-NMR spectrum are shown below. 1 H NMR (500MHz, CDCl3) δ(ppm): 6.917 (2H brs), 3.073 (4H quintet / J=5.4Hz), 1.775 (4H quintet / J=7.6Hz), 1.410-1.210 (32H, m), 0.876 (6H t / J=7.0Hz)

[0120] Comparative Synthesis Example 6 Comparative compound 6: Didecylammonium chlorate [(C 10 H 21 )2N + H2ClO3 - 〕 Didecylamine was dissolved in isopropanol to obtain an isopropanol solution of didecylamine. A solution of 60% by mass of chloric acid dissolved in isopropanol was added little by little to the obtained isopropanol solution of didecylamine until the whole became slightly acidic. The obtained solution was cooled to 10°C and filtered to obtain colorless crystals. The obtained crystals were recrystallized twice using isopropanol to obtain the target compound (comparative compound 6: didecylammonium chlorate).

[0121] The obtained comparative compound 6 1 The results of the H-NMR spectrum are shown below. 1 H NMR (500MHz, CDCl3) δ(ppm): 6.918 (2H brs), 3.073 (4H quintet / J=5.4Hz), 1.775 (4H quintet / J=7.0Hz), 1.396-1.190 (m, 28H), 0.874 (6H t / J=7.0Hz)

[0122] [Synthesis of dialkylammonium nitrates] [Synthesis Example 13] Compound 13: Decylundecylammonium nitrate [C 10 H 21 (C 11 H 23 )N + H2NO3 - 〕 A solution of undecylamine and 1.5 times the molar amount of triethylamine dissolved in chloroform was added dropwise to the solution of undecylamine and an equimolar amount of decanoic acid chloride dissolved in chloroform using a dropping funnel. After the dropwise addition was completed, the resulting chloroform solution was stirred at room temperature for 1 hour and then heated under reflux for 2 hours. The chloroform solution after heating under reflux was cooled to room temperature and washed with water. Anhydrous sodium sulfate was then added to the chloroform layer to remove water, and the solvent was then removed to obtain colorless crystals. The resulting crystals were recrystallized using a mixed solvent of chloroform and n-hexane to give N-undecyldecanamide (CH 19 CONHC11 H 23 ) was obtained. The N-undecyldecanamide obtained above and lithium aluminum hydride (LiAlH4) were added to anhydrous diethyl ether, and the mixture was refluxed for 2 hours, followed by a reaction at room temperature for 2 hours. After the reaction was completed, water was added to the resulting solution to decompose the excess lithium aluminum hydride. Next, anhydrous sodium sulfate was added to the diethyl ether layer to remove water, and the solvent was then removed to obtain crystals. The resulting crystals were heated and dissolved in n-hexane, then cooled, and the precipitated raw material N-undecyldecanamide was removed by filtration. The filtrate was concentrated to obtain decylundecylamine. Next, a solution of concentrated nitric acid dissolved in isopropanol was added in small amounts to a solution of decylundecylamine dissolved in isopropanol until the mixture became slightly acidic. The resulting solution was cooled to 10°C and filtered to obtain colorless crystals. The resulting crystals were recrystallized twice using n-hexane to obtain the target compound (Compound 13: decylundecylammonium nitrate).

[0123] The obtained compound 13 1 The results of the H-NMR spectrum and the infrared absorption spectrum by Fourier transform infrared spectroscopy (FT-IR) are shown below. 1 H NMR (500MHz, CDCl3) δ(ppm): 8.720 (2H, brs), 3.014-2.957 (4H, m), 1.721-1.660 (4H, m), 1.360-1.200 (m, 30H),0.869(6H, t / J=7.0Hz) FT-IR νmax (cm -1 ): 2957, 2855, 1637, 1472, 1354

[0124] [Synthesis Example 14] Compound 14: Undecyldodecylammonium nitrate [C 11 H 23 (C 12 H 25 )N + H2NO3 - 〕 A solution of dodecylamine and triethylamine in a molar amount 1.5 times that of the dodecylamine dissolved in chloroform was added dropwise using a dropping funnel to a solution of undecanoic acid chloride in an equimolar amount to the dodecylamine dissolved in chloroform. After the dropwise addition was completed, the resulting chloroform solution was stirred at room temperature for 1 hour and then heated under reflux for 2 hours. The chloroform solution after heating under reflux was cooled to room temperature and washed with water. Anhydrous sodium sulfate was then added to the chloroform layer to remove water, and the solvent was then removed to obtain colorless crystals. The resulting crystals were recrystallized using a mixed solvent of chloroform and n-hexane to give N-dodecylundecanoic acid amide (C 10 H 21 CONHC 12 H 25 ) was obtained. The N-dodecylundecaneamide obtained above and lithium aluminum hydride (LiAlH4) were added to anhydrous diethyl ether, and the mixture was refluxed for 2 hours, followed by a reaction at room temperature for 2 hours. After the reaction was completed, water was added to the resulting solution to decompose the excess lithium aluminum hydride. Next, anhydrous sodium sulfate was added to the diethyl ether layer to remove water, and the solvent was then removed to obtain crystals. The resulting crystals were heated and dissolved in n-hexane, then cooled, and the precipitated raw material N-dodecylundecaneamide was removed by filtration. The filtrate was concentrated to obtain undecyldodecylamine. Next, a solution of concentrated nitric acid dissolved in isopropanol was added in small amounts to a solution of undecyldodecylamine dissolved in isopropanol until the mixture became slightly acidic. The resulting solution was cooled to 10°C and filtered to obtain colorless crystals. The resulting crystals were recrystallized twice using n-hexane to obtain the target compound (Compound 14: undecyldodecylammonium nitrate).

[0125] The obtained compound 14 1 The results of the H-NMR spectrum and the infrared absorption spectrum by Fourier transform infrared spectroscopy (FT-IR) are shown below. 1H NMR (500MHz, CDCl3) δ(ppm): 8.727 (2H, brs), 3.011-2.954 (4H, m), 1.737-1.676 (4H, m), 1.360-1.200 (m, 34H),0.874(6H, t / J=7.0Hz) FT-IR νmax (cm -1 ): 2958, 2853, 1638, 1472, 1352

[0126] [Synthesis Example 15] Compound 15: Undecyltridecylammonium nitrate [C 11 H 23 (C 13 H 27 )N + H2NO3 - 〕 A solution of tridecylamine and triethylamine in an amount 1.5 times the molar amount of the tridecylamine dissolved in chloroform was added dropwise using a dropping funnel. After the dropwise addition, the resulting chloroform solution was stirred at room temperature for 1 hour and then heated under reflux for 2 hours. The chloroform solution after heating under reflux was cooled to room temperature and washed with water. Anhydrous sodium sulfate was then added to the chloroform layer to remove moisture, and the solvent was then removed to obtain colorless crystals. The resulting crystals were recrystallized using a mixed solvent of chloroform and n-hexane to give N-tridecylundecanoic acid amide (C 10 H 21 CONHC 13 H 27) was obtained. The N-tridecylundecaneamide obtained above and lithium aluminum hydride (LiAlH4) were added to anhydrous diethyl ether, and the mixture was refluxed for 2 hours, followed by a reaction at room temperature for 2 hours. After the reaction was completed, water was added to the resulting solution to decompose the excess lithium aluminum hydride. Next, anhydrous sodium sulfate was added to the diethyl ether layer to remove water, and the solvent was then removed to obtain crystals. The resulting crystals were heated and dissolved in n-hexane, then cooled, and the precipitated raw material N-tridecylundecaneamide was removed by filtration. The filtrate was concentrated to obtain undecyltridecylamine. Next, a solution of concentrated nitric acid dissolved in isopropanol was added in small amounts to a solution of undecyltridecylamine dissolved in isopropanol until the mixture became slightly acidic. The resulting solution was cooled to 10°C and filtered to obtain colorless crystals. The resulting crystals were recrystallized twice using n-hexane to obtain the target compound (Compound 15: undecyltridecylammonium nitrate).

[0127] The obtained compound 15 1 The results of the H-NMR spectrum and the infrared absorption spectrum by Fourier transform infrared spectroscopy (FT-IR) are shown below. 1 H NMR (500MHz, CDCl3) δ(ppm): 8.731 (2H, brs), 3.015-2.959 (4H, m), 1.735-1.674 (4H, m), 1.360-1.200 (m, 36H),0.876(6H, t / J=7.0Hz) FT-IR νmax (cm -1 ): 2957, 2854, 1638, 1471, 1353

[0128] [Synthesis Example 16] Compound 16: Undecyltetradecylammonium nitrate [C 11 H 23 (C 14 H 29 )N + H2NO3 - 〕 A solution of tetradecylamine and triethylamine in an amount 1.5 times the molar amount of the tetradecylamine dissolved in chloroform was added dropwise using a dropping funnel. After the dropwise addition, the resulting chloroform solution was stirred at room temperature for 1 hour and then heated under reflux for 2 hours. The chloroform solution after heating under reflux was cooled to room temperature and washed with water. Anhydrous sodium sulfate was then added to the chloroform layer to remove moisture, and the solvent was then removed to obtain colorless crystals. The resulting crystals were recrystallized using a mixed solvent of chloroform and n-hexane to obtain N-tetradecylundecanoic acid amide (C 10 H 21 CONHC 14 H 29 ) was obtained. The N-tetradecylundecaneamide obtained above and lithium aluminum hydride (LiAlH4) were added to anhydrous diethyl ether, and the mixture was refluxed for 2 hours, followed by a reaction at room temperature for 2 hours. After the reaction was completed, water was added to the resulting solution to decompose the excess lithium aluminum hydride. Next, anhydrous sodium sulfate was added to the diethyl ether layer to remove water, and the solvent was then removed to obtain crystals. The resulting crystals were heated and dissolved in n-hexane, then cooled, and the precipitated raw material N-tetradecylundecaneamide was removed by filtration. The filtrate was concentrated to obtain undecyltetradecylamine. Next, a solution of concentrated nitric acid dissolved in isopropanol was added in small amounts to a solution of undecyltetradecylamine dissolved in isopropanol until the mixture became slightly acidic. The resulting solution was cooled to 10°C and filtered to obtain colorless crystals. The resulting crystals were recrystallized twice using n-hexane to obtain the target compound (Compound 16: undecyltetradecylammonium nitrate).

[0129] The obtained compound 16 1 The results of the H-NMR spectrum and the infrared absorption spectrum by Fourier transform infrared spectroscopy (FT-IR) are shown below. 1H NMR (500MHz, CDCl3) δ(ppm): 8.734 (2H, brs), 3.009-2.954 (4H, m), 1.739-1.679 (4H, m), 1.370-1.194 (m, 38H),0.879(3H, t / J=7.0Hz), 0.876(3H, t / J=7.0Hz) FT-IR νmax (cm -1 ): 2958, 2854, 1636, 1471, 1354

[0130] [evaluation] (Examples 1 to 16 and Comparative Examples 1 to 6) The phase change temperature (unit: °C) and latent heat (unit: J / g) were measured for Compounds 1 to 16 synthesized in Synthesis Examples 1 to 16 and Comparative Compounds 1 to 6 synthesized in Comparative Synthesis Examples 1 to 6, and the presence or absence of repeatability and whether the phase change was a solid-solid phase change were confirmed. The results are shown in Tables 1 to 6 and Figures 1 to 5. The phase change temperature and latent heat were measured using a differential scanning calorimeter (model: DSC3200) manufactured by Mac Science under the following conditions: The phase change temperature is the temperature of the endothermic peak during heating, and the latent heat is the heat of the endothermic peak during heating. The presence or absence of cycle characteristics was judged by whether heat generation occurred during cooling. Specifically, if heat generation did not occur when the material was heated to 100°C and then cooled to 30°C over approximately one hour, it was determined not to have cycle characteristics. Whether or not a phase change is a solid-solid phase change was determined based on the presence or absence of melting before and after the phase change. Specifically, if there is no melting before or after the phase change, the phase change was determined to be a solid-solid phase change.

[0131] -conditions- Measurement temperature range: 30℃~100℃ Heating rate: 10℃ / min Atmospheric gas: Air Measurement sample amount: 6.0 mg

[0132] [Table 1]

[0133] [Table 2]

[0134] The results of Examples 1 to 4 are shown in Table 1, and the results of Comparative Examples 1 to 5 are shown in Table 2. Examples 1 to 4 and Comparative Examples 1 to 5 all use dialkylammonium nitrates having the same carbon number n and m in formula (I). Examples 1 to 4 and Comparative Examples 1 to 5 differ from each other in that the carbon numbers n and m in the former are odd numbers, while the carbon numbers n and m in the latter are even numbers. In all of Examples 1 to 4 and Comparative Examples 1 to 5, there was no melting before or after the phase change, and it was confirmed that the phase change was a solid-solid phase change. As shown in Table 1, it was found that Examples 1 to 4 all had a low phase change temperature of 60° C. or less, a large amount of latent heat, and had good repetitive characteristics. On the other hand, as shown in Table 2, Comparative Example 1 had a significantly small amount of latent heat and was found to have no cycling characteristics. Comparative Example 2 had a relatively large amount of latent heat at a low phase change temperature, but was found to have no cycling characteristics. Specifically, Comparative Examples 1 and 2 did not generate heat when cooled, and did not exhibit the initial endothermic behavior even when heated thereafter. Comparative Examples 3 to 5 were found to have phase change temperatures exceeding 60°C.

[0135] The latent heat amounts of Examples 1 to 4 and Comparative Examples 1 to 5 are shown in FIG. FIG. 1 shows that in the case of dialkylammonium nitrates in which the carbon numbers n and m in formula (I) are the same, Examples 1 to 4 in which the carbon numbers n and m are odd numbers have a clearly larger amount of latent heat than Comparative Examples 1 to 5 in which the carbon numbers n and m are even numbers.

[0136] The results shown in Tables 1 and 2 and FIG. 1 reveal that dialkylammonium nitrates in which the carbon numbers n and m in formula (I) are the same odd number have a significantly larger latent heat than dialkylammonium nitrates in formula (I) in which the carbon numbers n and m are the same even number, while maintaining a low phase change temperature of 60°C or less.

[0137] [Table 3]

[0138] [Table 4]

[0139] The results of Examples 5 to 7 are shown in Table 3 and Figure 2, and the results of Examples 8 to 10 are shown in Table 4 and Figure 3. Note that Comparative Example 3 shown in Table 3 and Figure 2 is listed for comparison with Examples 5 to 7 and is the same as Comparative Example 3 listed in Table 2 described above, and Comparative Example 4 shown in Table 4 and Figure 3 is listed for comparison with Examples 8 to 10 and is the same as Comparative Example 4 listed in Table 2 described above. Examples 5 to 10 are all dialkylammonium nitrates in which the carbon numbers n and m in formula (I) are different values, whereas Comparative Examples 3 and 4 are all dialkylammonium nitrates in which the carbon numbers n and m in formula (I) are the same even values. In all of Examples 5 to 10, there was no melting before or after the phase change, and it was confirmed that the phase change was a solid-solid phase change. As shown in Tables 3 and 4, it was found that Examples 5 to 10 all had a low phase change temperature of 60° C. or less, a high amount of latent heat, and had good repetitive characteristics. 2 shows that Examples 5 to 7 have a lower phase change temperature than Comparative Example 3 while maintaining a large amount of latent heat. Also, FIG. 3 shows that Examples 8 to 10 have a lower phase change temperature than Comparative Example 4 while maintaining a large amount of latent heat. The results shown in Tables 3 and 4 and Figures 2 and 3 reveal that dialkylammonium nitrates having different carbon numbers in formula (I) have lower phase change temperatures and larger latent heats than dialkylammonium nitrates having the same carbon number but an even value in formula (I).

[0140] [Table 5]

[0141] The results of Examples 11 and 12 and Comparative Example 6 are shown in Table 5 and FIG. Examples 11 and 12, and Comparative Example 6 are all dialkylammonium chlorates having the same carbon number n and m in formula (I). Examples 11 and 12 differ from Comparative Example 6 in that the carbon numbers n and m in the former are odd numbers, while the carbon numbers n and m in the latter are even numbers. In both Examples 11 and 12, there was no melting before or after the phase change, and it was confirmed that the phase change was a solid-solid phase change. As shown in Table 5, it was found that Examples 11 and 12 both had a low phase change temperature of 60°C or less, a large amount of latent heat, and had good repetitive characteristics. On the other hand, it was found that Comparative Example 6 had a phase change temperature of 60°C or less, but a significantly small amount of latent heat. 4, it can be seen that Examples 11 and 12 have clearly larger amounts of latent heat than Comparative Example 6. The results shown in Table 5 and FIG. 4 reveal that dialkylammonium chlorates in which the carbon numbers n and m in formula (I) are the same odd number have a significantly larger latent heat than dialkylammonium chlorates in which the carbon numbers n and m in formula (I) are the same even number, while maintaining a low phase change temperature of 60°C or less.

[0142] From the above, in the dialkylammonium compound which is a compound represented by the formula (I), not only for nitrates but also for chlorates, when the carbon numbers n and m in the formula (I) (i.e., the carbon numbers of the alkyl chains) are the same value, it was found that the latent heat amount is larger for odd values than for even values. These results suggest that the same effect can be achieved regardless of the type of X - in the formula (I).

[0143]

Table 6

[0144] The results of thermal analysis by DSC of Examples 13 to 16 are shown in Table 6. Comparative Example 3 described in Table 6 was described for comparison with Example 13 and is the same as Comparative Example 3 described in Table 2 above. Comparative Example 4 described in Table 6 was described for comparison with Example 14 and is the same as Comparative Example 4 described in Table 2 above. Comparative Example 5 described in Table 6 was described for comparison with Example 16 and is the same as Comparative Example 5 described in Table 2 above. Examples 13 to 16 are all dialkylammonium nitrates in which the carbon numbers n and m in the formula (I) are different values. It was confirmed that in Examples 13 to 16, there is no melting before and after the phase change, and the phase change is a solid-solid phase change. As shown in Table 6, it was found that in Examples 13 to 16, the phase change temperature is as low as 60°C or lower, the latent heat amount is high, and they have repeatability. From the results shown in Table 6, it was also revealed that dialkylammonium nitrates in which the carbon numbers n and m in the formula (I) are different values have a lower phase change temperature and a larger latent heat amount compared to dialkylammonium nitrates with the same carbon number and an even value.

[0145] <Measurement of X-ray diffraction spectrum> An X-ray diffraction spectrum of Compound 2 in powder form at 26°C and at 70°C after heating the sample holder was measured using an X-ray diffractometer manufactured by Rigaku Corporation (product name: SmartLab (registered trademark), X-ray source output: 9 kW). The X-ray diffraction spectra of Compound 2 before and after the phase change are shown in Figure 5. Figure 5 shows that there is a peak indicating a crystalline structure at the temperature before the phase change, but there is a peak indicating an amorphous structure after the phase change. It was also revealed that compound 2 returns to a crystalline structure by cooling at room temperature for two hours. These results suggest that the phase change of compound 2 is from crystalline to amorphous, i.e., a solid-solid phase change, and that the compounds of this series of examples have excellent repeatability during phase changes.

Claims

1. A latent heat storage material comprising a compound represented by the following formula (I): 【Chemistry 1】 In formula (I), when n=m, n represents an odd number of 7 to 13, and when n≠m, n and m each independently represent an integer of 7 to 14. X － represents a nitrate ion or a chlorate ion.

2. 2. The latent heat storage material according to claim 1, which has a phase change temperature of 60°C or less.

3. A latent heat storage material as described in claim 1 or claim 2, having a latent heat content of 90 J / g or more.

4. The latent heat storage material according to any one of claims 1 to 3, which is used in an electronic device or an electricity storage device.

5. A latent heat storage medium comprising the latent heat storage material according to any one of claims 1 to 3.

6. An electronic device comprising the latent heat storage material according to any one of claims 1 to 3.

7. An electricity storage device comprising the latent heat storage material according to any one of claims 1 to 3.

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