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

Abstract

The present application discloses a latent heat storage material, a latent heat storage body, an electronic device, and a power storage device. Specifically, a latent heat storage material containing a compound represented by the following formula (I) is disclosed. In formula (I), with respect to n and m, in the case where n = m, n represents an odd number, and in the case where n ≠ m, n and m each independently represent an integer of 6 to 24. X ‑ represents an anion. C n H 2n+1 (C m H 2m+1 )N + H2X ‑ (I)

Description

TECHNICAL FIELD

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

[0002] In recent years, in digital home electric appliances which are rapidly spreading, the heat release of electronic devices which handle high-speed and high-capacity information is increasing. In addition, with the development of miniaturization, weight reduction, and thinning, the importance of heat countermeasures for how to efficiently release heat from components is increasing. In particular, mobile devices such as smartphones and tablet personal computers (PCs) are rapidly developing in high functionality and high performance while being miniaturized, and the heat release density is significantly increasing. In mobile devices, the increase in the heat release density leads to an increase in the risk of thermal runaway, acceleration of solder fatigue caused by thermal cycles, and the like, and in order to improve reliability, it is required to take heat countermeasures.

[0003] As a cooling method for electronic devices, a passive cooling method using a phase change material (PCM) is attracting attention. The PCM is also called a latent heat storage material, and since it can absorb heat almost without changing the temperature by latent heat, if the PCM is used, an effect of delaying the time taken to raise the temperature, that is, a so-called delay effect can be obtained.

[0004] The latent heat storage material is a material which utilizes heat absorption and heat release at the time of a change in the state of a substance, and has an advantage that the heat storage capacity is larger than that of other heat storage materials, in addition to being reusable. As the latent heat storage material, for example, paraffin wax [melting point: 36.4°C (eicosane: C 20 H 42), sodium acetate trihydrate (melting point: 58°C), erythritol (melting point: 119°C), and the like. In addition, as a latent heat storage material, 1-hexadecyl-3-methylimidazolium chloride (for example, see E. Thomas, D. Thomas, S. Bhuvaneswari, K. P. Vijayalakshmi, B. K. George, "1-Hexadecyl-3-methylimidazolium chloride: Structure, thermal stability and decomposition mechanism", J. Mol. Liq., vol. 249 (2018), pp. 404-411. and 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 last but one "a" of the author, "M. Bendovaa", is "a" with an accent mark ', the "C" of "M. Canjia" is "C" with an accent mark ˇ, and the "s" of "N. Zdolsekc" is "s" with an accent mark ˇ)) as an imidazole-based ionic liquid are known. These compounds are all latent heat storage materials that utilize the latent heat of fusion that occurs with a phase change from a solid phase to a liquid phase.

[0005] In the case of cooling of a mobile device using a latent heat storage material that utilizes the latent heat of fusion that occurs with a phase change from a solid phase to a liquid phase as described above, there is a possibility that the latent heat storage material that has melted to become a liquid will leak to the outside of the mobile device. As one of the methods for solving this problem, a method of microencapsulating the latent heat storage material can be cited. However, if the latent heat storage material is microencapsulated, there is a disadvantage that the latent heat per unit volume decreases. The decrease in the latent heat per unit volume becomes a major cause of hindering the thinning of the mobile device. On the other hand, as a latent heat storage material that does not cause a leakage problem, there is a latent heat storage material that utilizes the latent heat that occurs with a phase change from a solid phase to a solid phase. As such a latent heat storage material, for example, 1,3-dimethylimidazolium chloride (chemical formula (C n H 2n+1 )2N+ H2NO3 - dialkylammonium nitrate represented by the formula: R1R2R3R4N (H2NO3) n (wherein, n represents an even number of 8 to 19) (for example, see S. Steinert, W. Voigt, R. Glausch, M. Neuschutz, "Thermal characteristics of solid-solid phase transitions in long-chain dialkylammonium salts" Thermochimica Acta vol. 435 (2005) pp. 28-33.).

[0006] However, in recent years, in order to efficiently use energy, electric vehicles equipped with high-performance batteries are becoming widespread. As high-performance batteries installed in electric vehicles, in particular, development of lithium-ion batteries is particularly active in order to achieve high output and high capacity of lithium-ion batteries. However, excessive high-temperature conditions caused by high output, and heat generated during charging and discharging in large quantities accompanying high capacity, become a major cause of significantly reducing the life of the battery, and in the worst case, there is a risk of causing fire and explosion. In general, for lithium-ion batteries, there is a tendency to significantly exhibit performance degradation in a use temperature region exceeding 60°C. Therefore, in order to optimize the battery characteristics, long life of the battery, and improvement of the safety of the battery, a heat management technology that maintains the temperature of the battery in an optimal temperature region (for example, 15°C to 60°C) is essential. In this regard, the dialkylammonium nitrate described in S. Steinert, W. Voigt, R. Glausch, M. Neuschutz, "Thermal characteristics of solid-solid phase transitions in long-chain dialkylammonium salts" Thermochimica Acta vol. 435 (2005) pp. 28-33. has a large latent heat per unit volume, but the phase transition temperature (also referred to as "phase transition temperature") tends to be high, and it is difficult to say that it is suitable as a latent heat storage material for a battery. SUMMARY

[0007] PROBLEMS TO BE SOLVED BY THE INVENTION

[0008] As described above, for a latent heat storage material, it is required to exhibit a low phase transition temperature of 60°C or less without causing a leakage problem caused by melting accompanying phase transition, and a large latent heat. Furthermore, the latent heat storage material requires a property of repeating heat absorption and heat release (so-called repetition property).

[0009] The present disclosure was completed in view of the above circumstances.

[0010] An object of one embodiment of the present disclosure is to provide a latent heat storage material which is a latent heat storage material utilizing latent heat generated with a phase change from a solid phase to a solid phase, which has a phase change temperature as low as 60°C or lower, a large amount of latent heat, and a repetition property.

[0011] An object of another embodiment of the present disclosure is to provide a latent heat storage body including the latent heat storage material described above, and an electronic device and a power storage device including the latent heat storage material.

[0012] Means for solving the problem

[0013] The present inventors focused on a dialkylammonium salt, which is a latent heat storage material utilizing latent heat generated with a phase change from a solid phase to a solid phase, in the course of repeated studies to solve the above problem. Furthermore, the present inventors found that the phase change temperature is lower and the amount of latent heat is larger when the number of carbons of two alkyl chains of a dialkylammonium salt is odd than when the number of carbons is even, in the case where the number of carbons of the two alkyl chains of the dialkylammonium salt is the same, after intensive studies on the dialkylammonium salt. In addition, the present inventors found that the dialkylammonium salt can lower the phase change temperature without reducing the amount of latent heat by setting the number of carbons of the two alkyl chains to specific different values, and thus completed the present disclosure.

[0014] Specific means for solving the above problem include the following aspects.

[0015] <1> A latent heat storage material containing a compound represented by the following chemical formula (I).

[0016] [Chemical Formula 1]

[0017] C n H 2n+1 (C m H 2m+1 )N + H2X - (I)

[0018] In the chemical formula (I), n and m are an odd number when n = m, and n and m each independently represent an integer of 6 to 24 when n ≠ m. - X represents an anion.

[0019] <2> The latent heat storage material according to <1>, in which n and m in the chemical formula (I) satisfy n = m, and n is an odd number of 5 to 17.

[0020] <3> The latent heat storage material according to <1> or <2>, in which X in the chemical formula (I) is -represents a nitrate ion or a chlorate ion.

[0021] <4> The latent heat storage material according to any one of <1> to <3>, which is used for an electronic device or a power storage device.

[0022] <5> A latent heat storage body comprising the latent heat storage material according to any one of <1> to <3>.

[0023] <6> An electronic device comprising the latent heat storage material according to any one of <1> to <3>.

[0024] <7> A power storage device comprising the latent heat storage material according to any one of <1> to <3>.

[0025] Inventive Effects

[0026] According to one embodiment of the present disclosure, there is provided a latent heat storage material that is a latent heat storage material utilizing latent heat generated accompanying a phase change from a solid phase to a solid phase, which has a phase change temperature as low as 60°C or lower, a large amount of latent heat, and a repetition property.

[0027] According to another embodiment of the present disclosure, there is provided a latent heat storage body comprising the above-described latent heat storage material, and an electronic device and a power storage device comprising the above-described latent heat storage material. BRIEF DESCRIPTION OF DRAWINGS

[0028] Figure 1 is a graph showing the relationship between the number of carbons n (n = m in Chemical Formula (I)) of the compounds in Examples 1 to 4 and Comparative Examples 1 to 5 and the amount of latent heat.

[0029] Figure 2 is a graph showing the relationship between the numbers of carbons 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.

[0030] Figure 3 is a graph showing the relationship between the numbers of carbons 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.

[0031] Figure 4 is a graph showing the relationship between the numbers of carbons n and m of the compounds in Example 11 and Example 12, and Comparative Example 6 and the phase change temperature and the amount of latent heat.

[0032] Figure 5 is a graph showing the X-ray diffraction spectrum of the compound 2 obtained in Synthesis Example 2. DETAILED DESCRIPTION

[0033] Hereinafter, the latent heat storage material of the present disclosure, the latent heat storage body containing the above latent heat storage material, and the electronic device and the power storage device including the above latent heat storage material will be described in detail. The description of the elements described below is sometimes based on representative embodiments of the present disclosure, but the present disclosure is not limited to such embodiments, and can be appropriately modified and implemented within the scope of the objects of the present disclosure.

[0034] In the present disclosure, a numerical range indicated using "~" means a range including the numerical values described before and after "~" as lower limit values and upper limit values, respectively.

[0035] In the numerical ranges described step by step in the present disclosure, the upper limit value or the lower limit value described in a certain numerical range can be replaced with the upper limit value or the lower limit value of the numerical range described at another stage. In addition, in the numerical ranges described in the present disclosure, the upper limit value or the lower limit value described in a certain numerical range can be replaced with the value shown in the examples.

[0036] In the present disclosure, a combination of two or more preferred aspects is a more preferred mode.

[0037] In the present disclosure, in the case where a plurality of substances corresponding to each component are present in the latent heat storage material, unless otherwise specified, the amount of each component in the latent heat storage material means the total amount of the above plurality of substances present in the latent heat storage material. In addition, the same applies to the latent heat storage body.

[0038] [Latent heat storage material]

[0039] The latent heat storage material of the present disclosure includes a compound represented by the above Chemical Formula (I).

[0040] The latent heat storage material of the present disclosure is a latent heat storage material that utilizes latent heat generated in association with a phase change from a solid phase to a solid phase, and has a phase change temperature as low as 60°C or lower, a large amount of latent heat, and a repetition property.

[0041] The present inventors have found that, in the case where the carbon numbers of the two alkyl chains of a dialkylammonium salt are the same, the phase change temperature is lower and the amount of latent heat is larger when the carbon number is odd than when the carbon number is even. In addition, it has been found that a dialkylammonium salt can lower the phase change temperature without reducing the amount of latent heat by setting the carbon numbers of the two alkyl chains to different specific values, respectively.

[0042] For the latent heat storage material of the present disclosure, the carbon number of the two alkyl chains of the dialkylammonium nitrate represented by the chemical formula (C n H 2n+1 )2N + H2NO3 - is the same even number, although the latent heat amount is large, there is a tendency for the phase transition temperature to increase. In the case where the carbon number of the two alkyl chains of the dialkylammonium nitrate is the same even number, the phase transition temperature and the latent heat amount are related to the value of n (i.e., the carbon number of the alkyl chain), and there is a trade-off relationship in which the phase transition temperature becomes lower and the latent heat amount becomes smaller as the value of n becomes smaller. Furthermore, in the case where the carbon number of the two alkyl chains of the dialkylammonium nitrate is the same even number, the repeat property is not exhibited when the value of n is small.

[0043] Furthermore, it is known that the enthalpy change of the dialkylammonium salt has a strong relationship with the symmetry of the alkyl chain [for example, see M.J.M. van Oort, M.A. White, Ber. Bunsenges. Phys. Chem. 92 (1988) 168.]. In addition, it is also known that the properties of an organic compound change depending on whether the carbon number is even or odd (so-called odd-even effect) [for example, see F. Tao, S.L. Bernasek, "Understanding Odd-Even Effects in Organic Self-Assembled Monolayers", Chem. Rev. 2007, Vol. 107, pp. 1408-1453.].

[0044] However, it is difficult to predict the effect of the latent heat amount depending on whether the carbon number is even or odd. For example, it is reported that in the case of long-chain alkanes, the latent heat amount shows an odd-even effect, and the latent heat amount of long-chain alkanes having an even carbon number is greater than that of long-chain alkanes having an odd carbon number, in contrast to which, in the case of long-chain carboxylic acids, the latent heat amount does not show an odd-even effect [for example, see 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.]. From these examples, it is known that the odd-even effect related to the latent heat amount differs depending on the kind of compound, and thus it can be said that it is difficult to predict definitely.

[0045] [compound represented by chemical formula (I)]

[0046] The latent heat storage material of the present disclosure includes a compound represented by the following chemical formula (I).

[0047] [chemical formula 2]

[0048] C n H 2n+1 (C m H m+1 )N + H2X - (I)

[0049] In chemical formula (I), with respect to n and m, in the case of n = m, n represents an odd number. n preferably represents an odd number of 5 to 17, more preferably an odd number of 5 to 15, further preferably an odd number of 5 to 13, particularly preferably an odd number of 7 to 13.

[0050] In chemical formula (I), in the case of n = m, if n is an odd number of 5 or more, the latent heat amount has a tendency to further increase. Furthermore, in chemical formula (I), in the case of n = m, if n is an odd number of 5 to 17, there is a tendency for phase transition (also referred to as "phase change") to easily occur within the optimum temperature range (for example, 25°C to 60°C) after use of the latent heat storage material.

[0051] In chemical formula (I), with respect to n and m, in the case of 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, further preferably an integer of 6 to 18, further preferably an integer of 6 to 16, particularly preferably an integer of 7 to 14.

[0052] In the chemical formula (I), in the case where n≠m, if n and m are each independently an integer of 6 or more, there is a tendency that the latent heat amount further increases. In addition, in the chemical formula (I), in the case where n≠m, if n and m are each independently an integer of 6 to 24, there is a tendency that the phase transition (also referred to as "phase change") easily occurs within the optimum temperature range (for example, 25°C to 60°C) after the latent heat storage material is used.

[0053] In the chemical formula (I), X - represents an anion.

[0054] As the anion represented by X - , there is no particular limitation, and for example, nitrate ion (NO3 - ), chlorate ion (CIO3 - ), fluoride ion (F - ), chloride ion (Cl - ), bromide ion (Br - ), iodide ion (I - ), hydrogen sulfate ion (HSO4 - ), perchlorate ion (CIO4 - ), dihydrogen phosphate ion (H2PO4 - ), trifluoromethanesulfonate ion (CF3SO3 - ), bis(trifluoromethylsulfonyl)imide ion 〔(CF3SO)2N - 〕, tetrafluoroborate ion (BF4 - ), hexafluorophosphate ion (PF6 - ), trifluoroacetate ion (CF3COO - ), and acetate ion (CH3COO - ) can be exemplified.

[0055] X - preferably represents nitrate ion or chlorate ion, and more preferably represents nitrate ion.

[0056] The latent heat storage material of the present disclosure can contain only one compound represented by the chemical formula (I), or can contain two or more.

[0057] The content of the compound represented by the chemical formula (I) in the latent heat storage material of the present disclosure is not particularly limited, and for example, relative to the total solid content amount in the latent heat storage material, it is preferably 30 mass% to 100 mass%, more preferably 50 mass% to 100 mass%, and further preferably 70 mass% to 100 mass%.

[0058] In the present disclosure, the "total solid content amount in the latent heat storage material" refers to the total mass of the latent heat storage material in the case where the latent heat storage material does not contain a solvent, and refers to the mass of the residue after the solvent is removed from the latent heat storage material in the case where the latent heat storage material contains a solvent.

[0059] In the present disclosure, "solvent" refers to water and an organic solvent.

[0060] 〔Synthesis method of compound represented by Chemical Formula (I)〕

[0061] The synthesis method of the compound represented by Chemical Formula (I) is not particularly limited.

[0062] The compound represented by Chemical Formula (I) can be synthesized by a publicly known method. Specifically, the compound represented by Chemical Formula (I) can be synthesized by the method described in the examples.

[0063] The compound represented by Chemical Formula (I) can be synthesized, for example, according to the method described in, for example, the above-mentioned 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 by reference into the present application.

[0064] 〔Binder〕

[0065] The latent heat storage material of the present disclosure can include a binder.

[0066] As the binder, for example, a thermoplastic resin and a thermosetting resin can be cited.

[0067] As the thermoplastic resin, for example, an acrylic resin, a polyacetal, a polyamide, a polyethylene, a polypropylene, a polyethylene terephthalate, a polybutylene terephthalate, a polycarbonate, a polystyrene, a polyphenylene sulfide, a polyvinyl chloride, an acrylonitrile butadiene styrene (ABS) resin, and a styrene-acrylonitrile (AS) resin can be cited.

[0068] As the thermosetting resin, for example, a phenol resin, an epoxy resin, a melamine resin, a urea resin, an unsaturated polyester, a diallyl phthalate resin, a urethane resin, and a silicone resin can be cited.

[0069] Further, as the binder, for example, rubber can be cited.

[0070] As the rubber, for example, butadiene rubber, isoprene rubber, chloroprene rubber, halogenated butyl rubber, fluoro rubber, urethane rubber, acrylic rubber (ACM) obtained by copolymerization of acrylate with other monomers, ethylene-propylene rubber obtained by coordination polymerization of ethylene and propylene using Ziegler catalyst, butyl rubber (IIR) obtained by copolymerization of isobutylene and isoprene, butadiene styrene rubber (SBR) obtained by copolymerization of butadiene and styrene, butyronitrile rubber (NBR) obtained by copolymerization of acrylonitrile and butadiene, and silicone rubber can be cited.

[0071] Further, as the binder, for example, thermoplastic elastomer (TPE) can be cited.

[0072] As the thermoplastic elastomer, for example, olefin-based thermoplastic elastomer (TPO), styrene-based thermoplastic elastomer (TPS), amide-based thermoplastic elastomer (TPA), and polyester-based thermoplastic elastomer (TPC) can be cited.

[0073] The latent heat storage material of the present disclosure, in the case of containing a binder, can contain only one kind of binder, or can contain two or more kinds.

[0074] In the case where the latent heat storage material of the present disclosure contains a binder, the content of the binder is not particularly limited, but for example, it is preferably 50% by weight or more and 95% by weight or less, more preferably 60% by weight or more and 95% by weight or less, and further preferably 70% by weight or more and 90% by weight or less, with respect to the total solid content amount in the latent heat storage material.

[0075] [Other Components]

[0076] The latent heat storage material of the present disclosure, within a range not impairing the effects thereof, can contain components other than the above components (so-called other components) as necessary.

[0077] As the other components, various additives such as dispersants, dispersion aids, antifungal agents, antistatic agents, antioxidants, binding agents, thermally conductive materials, flame retardant materials, and the like can be cited. The additive can be an additive in which one component assumes two or more functions.

[0078] The latent heat storage material of the present disclosure, in the case of containing rubber as the binder, can contain, in addition to the rubber, vulcanizing agents, vulcanizing aids, softening agents, plasticizers, and the like.

[0079] As the vulcanizing agent, for example, sulfur, organic sulfur compounds, and metal oxides can be cited.

[0080] In the case where the latent heat storage material of the present disclosure contains other components, the content of the other components can be appropriately set within a range that does not impair the effects of the latent heat storage material of the present disclosure.

[0081] <<Phase change temperature and latent heat amount>>

[0082] The phase change temperature of the latent heat storage material of the present disclosure is 60°C or lower, preferably 55°C or lower, more preferably 50°C or lower, and further preferably 45°C or lower.

[0083] When the phase change temperature of the latent heat storage material of the present disclosure is 60°C or lower, there is a tendency that the performance deterioration of an article (for example, an electronic device, a battery, or the like) to which the latent heat storage material is applied can be well suppressed.

[0084] The lower limit of the phase change temperature of the latent heat storage material of the present disclosure is not particularly limited, and is, for example, preferably 15°C or higher, more preferably 20°C or higher, and further preferably 25°C or higher.

[0085] The latent heat amount of the latent heat storage material of the present disclosure is not particularly limited, and is, for example, preferably 90 J / g or higher, more preferably 100 J / g or higher, further preferably 110 J / g or higher, and particularly preferably 120 J / g or higher.

[0086] The higher the latent heat amount of the latent heat storage material of the present disclosure is, the more preferable it is, and the upper limit is not particularly limited.

[0087] The phase change temperature of the latent heat storage material of the present disclosure is the temperature of the endothermic peak at the time of temperature increase, which is measured according to the following conditions, using a differential scanning calorimeter (DSC: Differential Scanning Calorimeter) as a measuring device.

[0088] The latent heat amount of the latent heat storage material of the present disclosure is the heat amount of the endothermic peak at the time of temperature increase, which is measured according to the following conditions, using a differential scanning calorimeter as a measuring device.

[0089] As the differential scanning calorimeter, for example, a differential scanning calorimeter [Model: DSC3200] manufactured by Mac Science Co., Ltd. can be preferably used. However, the differential scanning calorimeter is not limited thereto.

[0090] -Conditions-

[0091] Measurement temperature range: 30°C to 100°C

[0092] Temperature increase rate: 10°C / min

[0093] Atmosphere gas: air

[0094] Measurement sample amount: 6.0 mg

[0095] <Use of latent heat storage material>

[0096] The use of the latent heat storage material of the present disclosure is not particularly limited.

[0097] The latent heat storage material of the present disclosure is a latent heat storage material that utilizes latent heat generated along with a phase change from a solid phase to a solid phase. The latent heat storage material of the present disclosure has a phase change temperature as low as 60°C or lower, a large amount of latent heat, and a repetition characteristic, and is thus preferably used as a latent heat storage material for electronic devices or power storage devices.

[0098] Specific examples of electronic devices and power storage devices are described later, and thus the description is omitted here.

[0099] The latent heat storage material of the present disclosure is a latent heat storage material that utilizes latent heat generated along with a phase change from a solid phase to a solid phase. Thus, unlike existing PCMs (for example, paraffin, sodium acetate trihydrate, erythritol, 1-hexadecyl-3-methylimidazolium chloride, and the like) that become liquid by melting along with a phase change from a solid phase to a liquid phase, the latent heat storage material of the present disclosure does not become liquid by melting, and thus does not have a problem of leakage. Furthermore, the latent heat storage material of the present disclosure is a latent heat storage material that has a phase change temperature as low as 60°C or lower, a large amount of latent heat, and a repetition characteristic, and thus can maintain the characteristics, life, and safety of electronic devices and power storage devices for a long period of time. The latent heat storage material of the present disclosure is particularly preferably used as a latent heat storage material for a power storage device that has a high output and a high capacity along with generation of a large amount of heat at a high temperature.

[0100] [Latent heat storage body]

[0101] The latent heat storage body of the present disclosure includes the latent heat storage material of the present disclosure.

[0102] The latent heat storage body of the present disclosure has a phase change temperature as low as 60°C or lower, a large amount of latent heat, and a repetition characteristic, because it includes the latent heat storage material of the present disclosure.

[0103] The shape of the latent heat storage body of the present disclosure is not particularly limited, and can be appropriately set according to the purpose.

[0104] The latent heat storage body of the present disclosure can have a planar shape or a three-dimensional shape.

[0105] As the planar shape, for example, a sheet shape and a film shape can be cited.

[0106] The three-dimensional shape is not particularly limited, and can be appropriately set according to the shape of an object to which the latent heat storage body of the present disclosure is applied.

[0107] The method for producing the latent heat accumulator of the present disclosure is not particularly limited.

[0108] The latent heat accumulator of the present disclosure can be produced, for example, by a publicly known method using the latent heat storage material and the solvent of the present disclosure.

[0109] The latent heat accumulator of the present disclosure can be produced, for example, by the following Method X.

[0110] (Method X)

[0111] The latent heat accumulator-forming composition including the latent heat storage material of the present disclosure containing the compound represented by Chemical Formula (I) and the binder, and the solvent is coated on a temporary support to form a coated film of the latent heat accumulator-forming composition. Subsequently, the latent heat accumulator is formed on the temporary support by drying the coated film of the latent heat accumulator-forming composition. Subsequently, by peeling the temporary support from the latent heat accumulator, a planar latent heat accumulator can be produced.

[0112] The solvent in Method X is not particularly limited, and for example, water, an organic solvent, or a mixed solvent of water and an organic solvent can be exemplified.

[0113] As the organic solvent, for example, alcohol-based solvents (e.g., methanol, ethanol, n-propanol, and isopropanol), 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 can be exemplified.

[0114] The content of the solvent in the latent heat accumulator-forming composition is not particularly limited, and can be appropriately set according to the kind and amount of the components to be compounded in the latent heat accumulator-forming composition.

[0115] The compound represented by Chemical Formula (I) and the binder in the latent heat accumulator-forming composition are simply mixed.

[0116] The method for mixing the compound represented by Chemical Formula (I) and the binder is not particularly limited, and for example, a method for mixing by stirring can be exemplified.

[0117] The stirring means is not particularly limited, and a general stirring device can be used.

[0118] As the stirring device, for example, a mixer such as a paddle mixer or an impeller mixer can be exemplified.

[0119] The stirring time is not particularly limited, and can be appropriately set according to the kind of the stirring device, the composition of the latent heat accumulator-forming composition, and the like.

[0120] The temporary support body is not particularly limited.

[0121] As the temporary support body, for example, a metal plate, a glass plate, a resin sheet, and various films can be listed.

[0122] The resin sheet is preferably subjected to a release treatment on the surface.

[0123] The size of the temporary support body is not particularly limited, and can be appropriately set, for example, in accordance with the size of the latent heat storage body.

[0124] The thickness of the temporary support body is not particularly limited, and can be appropriately set, for example, in consideration of workability.

[0125] The method of applying the latent heat storage body-forming composition on the temporary support body is not particularly limited, and for example, a method using a die coater, a knife coater, an applicator, or the like can be listed.

[0126] As the method of drying the applied film of the latent heat storage body-forming composition, a method using a heating device such as an oven can be listed, for example.

[0127] The drying temperature and the drying time are not particularly limited, as long as the solvent contained in the applied film of the latent heat storage body-forming composition can be volatilized.

[0128] Alternatively, the latent heat storage body of the present disclosure can be manufactured, for example, by the following Method Y.

[0129] (Method Y)

[0130] A mixture of the latent heat storage material of the present disclosure including the compound represented by Chemical Formula (I) and the binder, and a solvent used as necessary, is kneaded using a kneader while being heated, to obtain a kneaded product. Subsequently, by subjecting the obtained kneaded product to molding processing, the latent heat storage body of the present disclosure can be manufactured.

[0131] The solvent in Method Y is synonymous with the solvent in Method X.

[0132] In the case where the mixture contains a solvent, the content of the solvent in the mixture is not particularly limited, and can be appropriately set, for example, in accordance with the kind and the amount of the components to be compounded in the mixture.

[0133] In the mixture, the compound represented by Chemical Formula (I) and the binder are simply mixed.

[0134] The method of mixing the compound represented by Chemical Formula (I) and the binder is not particularly limited, and for example, a method of mixing by stirring can be listed.

[0135] As the stirring means, a general stirring device can be used without particular limitation.

[0136] As the stirring device, for example, a paddle mixer, an impeller mixer, or the like can be exemplified.

[0137] The stirring time is not particularly limited, and can be appropriately set according to the kind of the stirring device, the composition of the mixture, or the like.

[0138] The heating temperature of the mixture is not particularly limited, and can be appropriately set according to the kind of the binder, for example.

[0139] The heating temperature is preferably a temperature at which the binder is melted, and can be set to 170°C to 200°C, for example.

[0140] As the kneading means, a general kneading device can be used without particular limitation.

[0141] As the kneading device, a mixer, a two-roll kneader, a kneader, or the like can be exemplified.

[0142] The kneading conditions are not particularly limited, and can be appropriately set according to the kind of the kneading device, the composition of the mixture, or the like.

[0143] As the molding processing, for example, processing using press molding, extrusion molding, injection molding, in-mold molding, molding using a three-dimensional molding machine, or the like can be exemplified.

[0144] The molding processing is not particularly limited, and can be appropriately set according to the kind of the molding processing device, the composition of the mixture, and the size of the latent heat accumulator, for example.

[0145] [Electronic device]

[0146] The electronic device of the present disclosure includes the latent heat storage material of the present disclosure, and can include a latent heat accumulator containing the latent heat storage material of the present disclosure (i.e., the latent heat accumulator of the present disclosure).

[0147] Since the electronic device of the present disclosure includes the latent heat storage material of the present disclosure, a problem of leakage due to melting does not occur. Furthermore, since the electronic device of the present disclosure includes the latent heat storage material of the present disclosure, the characteristics, the life, and the safety of the electronic device can be maintained for a long period of time.

[0148] As the electronic device of the present disclosure, for example, a semiconductor device such as an integrated circuit (IC) or an IC module, and a light emitting diode (LED) device can be exemplified.

[0149] The aspect of the electronic device of the present disclosure including the latent heat storage material of the present disclosure is not particularly limited.

[0150] As an aspect of the electronic device of the present disclosure, for example in the case of a semiconductor device, an aspect in which the latent heat accumulator (i.e., the latent heat accumulator containing the latent heat storage material of the present disclosure) of the present disclosure having a planar shape (e.g., a sheet shape) is disposed between the semiconductor device and a heat sink can be exemplified. According to such an aspect, the compound represented by Chemical Formula (I) contained in the latent heat storage material of the present disclosure absorbs heat generated in the semiconductor device as latent heat, and the compound represented by Chemical Formula (I) undergoes a phase change. During the phase change, the temperature is kept constant, and thus it is possible to keep the semiconductor device at a constant temperature. The heat stored by the compound represented by Chemical Formula (I) is transferred, for example, by the heat sink, and dissipated.

[0151] [Power storage device]

[0152] The power storage device of the present disclosure includes the latent heat storage material of the present disclosure, and can include the latent heat accumulator (i.e., the latent heat accumulator of the present disclosure) containing the latent heat storage material of the present disclosure.

[0153] Since the power storage device of the present disclosure includes the latent heat storage material of the present disclosure, there is no problem of leakage due to melting. Furthermore, since the power storage device of the present disclosure includes the latent heat storage material of the present disclosure, it is possible to maintain the characteristics, the life, and the safety of the power storage device for a long period of time.

[0154] As the power storage device of the present disclosure, for example, a battery can be exemplified.

[0155] As the battery, for example, a lead storage battery, an alkaline storage battery, a nickel-cadmium battery, a lithium ion battery, and a full solid battery can be exemplified.

[0156] The aspect of the power storage device of the present disclosure including the latent heat storage material of the present disclosure is not particularly limited.

[0157] In the case where the power storage device of the present disclosure is a battery, for example, an aspect in which a three-dimensional latent heat accumulator (i.e., the latent heat accumulator containing the latent heat storage material of the present disclosure) of the present disclosure is disposed between the battery cells and / or between the battery cells and a heat sink in a manner so as to cover all or a part of the battery cells can be exemplified. According to such an aspect, the compound represented by Chemical Formula (I) contained in the latent heat storage material of the present disclosure absorbs heat generated in the battery cells as latent heat, and the compound represented by Chemical Formula (I) undergoes a phase change. During the phase change, the temperature is kept constant, and thus it is possible to keep the battery module at a constant temperature. The heat stored by the compound represented by Chemical Formula (I) is transferred, for example, by the heat sink, and dissipated.

[0158] [Example]

[0159] The latent heat storage material of this disclosure will be described in more detail below through embodiments. This disclosure is not limited to the following embodiments without departing from its spirit.

[0160] For the measurement of nuclear magnetic resonance (NMR) spectra of each compound, a Varian NMR apparatus (model: UNITY INOVA 500 (500MHz)) was used. Furthermore, for the measurement of infrared absorption spectra of each compound, a Fourier transform infrared spectrophotometer (model: FT / IR-400) manufactured by Nippon Spectrophotometer Co., Ltd. was used. Additionally, elemental analysis of each compound was performed using a fully automated elemental analyzer (CHNS / O) (model: 2400II series) manufactured by PerkinElmer.

[0161] Synthesis of dialkylammonium nitrates

[0162] [Synthesis example 1]

[0163] Compound 1: Diheptylammonium nitrate [(C7H] 15 )2N + H2NO3 - ]

[0164] A solution of diheptylamine dissolved in isopropanol was prepared by adding small amounts of concentrated nitric acid dissolved in isopropanol each time until the overall solution was weakly acidic. The resulting liquid was cooled to 10°C and filtered to obtain colorless crystals. The crystals were recrystallized twice using a mixed solvent of hexane and ethanol to obtain the target compound (compound 1: diheptylammonium nitrate).

[0165] The obtained compound 1 1 The results of H-NMR spectra and infrared absorption spectra obtained by Fourier transform infrared spectroscopy (FT-IR) are shown below.

[0166] 1 H-NMR (500MHz, CDCl3) δ (ppm): 8.766 (2H brs), 3.010-2.970 (4H m), 1.711 (4Hquintet / J=7.6Hz), 1.322-1.204 (m, 16H), 0.875 (6H t / J=7.0Hz)

[0167] FT-IRνmax(cm -1 ):3014,2958,2918,2853,1624,1470,1350

[0168] The elemental analysis results of compound 1 are shown below.

[0169] Calculated value (%) (C) 14 H 32 N2O3):C,60.83;H,11.67;N,10.13

[0170] Measured values ​​(%): C, 60.97; H, 11.77; N, 10.30

[0171] [Synthesis example 2]

[0172] Compound 2: Dinonylammonium nitrate [(C9H] 19 )2N + H2NO3 - ]

[0173] A solution was prepared by dissolving nonylamine and triethylamine (1.5 times the molar amount of nonylamine) in chloroform. Using a dropping funnel, a solution was prepared by adding nonanoic acid chloride (equal in molar amount to nonylamine) dissolved in chloroform. After the addition was complete, the resulting chloroform solution was stirred at room temperature for 1 hour and then refluxed for 2 hours. The refluxed chloroform solution was cooled to room temperature and washed with water. Next, anhydrous sodium sulfate was added to the chloroform layer to remove water and solvent, yielding colorless crystals. The crystals were recrystallized using a mixed solvent of chloroform and n-hexane to obtain N-nonylnonamide (C8H2O). 17 CONHC9H 19 N-Nonylnonamide and lithium aluminum hydride (LiAlH4) obtained above were added to anhydrous diethyl ether, refluxed for 2 hours, and then reacted at room temperature for 2 hours. After the reaction was completed, water was added to the resulting liquid to decompose the excess lithium aluminum hydride. Then, anhydrous sodium sulfate was added to the diethyl ether layer to remove water, and the solvent was removed to obtain crystals. The crystals were recrystallized twice with n-hexane to obtain di-n-nonylamine. Then, a solution of concentrated nitric acid dissolved in isopropanol was added in small amounts each time to the solution obtained by dissolving di-n-nonylamine in isopropanol until the overall solution was weakly acidic. The resulting liquid was cooled to 10°C and filtered to obtain colorless crystals. The crystals were recrystallized twice with a mixed solvent of chloroform and n-hexane to obtain the target compound (compound 2: di-nonylammonium nitrate).

[0174] The obtained compound 2 1 The results of H-NMR spectra and infrared absorption spectra obtained by Fourier transform infrared spectroscopy (FT-IR) are shown below.

[0175] 1H NMR (500 MHz, CDC13) δ (ppm) : 8.742 (2H br s), 2.987-2.956 (4H m), 1.696 (4H quintet / J = 7.6 Hz), 1.350-1.190 (m, 24H), 0.865 (6H t / J = 7.0 Hz)

[0176] FT-IR vmaχ (cm -1 ): 3015, 2957, 2919, 2853, 1624, 1470, 1350

[0177] The elemental analysis results of the obtained compound 2 are shown below.

[0178] Calculated (%) (C 18 H 40 N2O3) : C, 65.02; H, 12.13; N, 8.42

[0179] Measured (%) : C, 64.85; H, 12.22; N, 8.37

[0180] Synthesis Example 3

[0181] Compound 3: diundecylammonium nitrate [(C 11 H 23 )2N + H2NO3 - ]

[0182] To a solution in which undecylamine and triethylamine in a molar amount 1.5 times that of the above undecylamine were dissolved in chloroform, a solution in which undecanoic acid chloride in a molar amount equal to that of the above undecylamine was dissolved in chloroform was added dropwise using a dropping funnel. After the dropwise addition was completed, the resulting chloroform solution was stirred at normal temperature for 1 hour and then heated to reflux for 2 hours. After the chloroform solution heated to reflux was cooled to normal temperature, it was washed with water. Next, anhydrous sodium sulfate was added to the chloroform layer, and after the water was removed, the solvent was removed to obtain a colorless crystal. The obtained crystal was recrystallized using a mixed solvent of chloroform and n-hexane to obtain N-undecylundecanamide (C 10 H 21 CONHC 11 H 23). To the N-undecyl undecanoic amide obtained by the above and lithium aluminum hydride (LiAlH4) in dry ether, reflux was carried out for 2 hours and reaction was carried out at normal temperature for 2 hours. After the completion of the reaction, water was added to the obtained liquid to decompose the excess lithium aluminum hydride. Next, anhydrous sodium sulfate was added to the ether layer, and after removing the water, the solvent was removed to obtain crystals. The obtained crystals were recrystallized twice using n-hexane to obtain di-n-undecylamine. Next, to the solution in which di-n-undecylamine was dissolved in isopropyl alcohol, a solution in which concentrated nitric acid was dissolved in isopropyl alcohol was added little by little until the whole became weakly acidic. The obtained liquid was cooled to 10°C, and then 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: di-n-undecylammonium nitrate).

[0183] The results of the elemental analysis of the obtained Compound 3 are shown below. 1 The results of H-NMR spectrum and infrared absorption spectrum by Fourier transform infrared spectroscopy (FT-IR) are shown below.

[0184] 1 H NMR (500 MHz, CDC13) δ (ppm) : 8.805 (2H brs), 3.010-2.930 (4H m), 1.727 (4H quintet / J = 7.8 Hz), 1.360-1.204 (32H, m), 0.874 (6H t / J = 7.0 Hz)

[0185] FT-IR vmaχ (cm -1 ): 3014, 2957, 2917, 2853, 1624, 1471, 1353

[0186] The results of the elemental analysis of the obtained Compound 3 are shown below.

[0187] Calculated (%) (C 22 H 48 N2O3) : C, 67.99; H, 12.45; N, 7.21

[0188] Measured (%) : C, 68.13; H, 12.66; N, 6.87

[0189] [Synthesis Example 4]

[0190] Compound 4: di-n-tridecylammonium nitrate [(C 13 H 27 )2N + H2NO3 - ]

[0191] A solution was prepared by dissolving tridecylamine and triethylamine (1.5 times the molar amount of tridecylamine) in chloroform. Using a dropping funnel, a solution of tridecaneacid chloride (equal in molar amount to tridecylamine) dissolved in chloroform was added dropwise. After the addition was complete, the resulting chloroform solution was stirred at room temperature for 1 hour and then refluxed for 2 hours. The refluxed chloroform solution was cooled to room temperature and washed with water. Next, anhydrous sodium sulfate was added to the chloroform layer to remove water, and then the solvent was removed to obtain colorless crystals. The crystals were recrystallized using a mixed solvent of chloroform and n-hexane to obtain N-tetrazyltridecylamide (C...). 12 H 25 CONHC 13 H 27 N-Tetrazyltridecylamide and lithium aluminum hydride (LiAlH4) obtained above were added to anhydrous diethyl ether, refluxed for 2 hours, and then reacted at room temperature for 2 hours. After the reaction was completed, water was added to the resulting liquid to decompose the excess lithium aluminum hydride. Then, anhydrous sodium sulfate was added to the diethyl ether layer to remove water, and then the solvent was removed to obtain crystals. The crystals were recrystallized twice with n-hexane to obtain ditridecylamine. Then, a solution of concentrated nitric acid dissolved in isopropanol was added in small amounts each time to the solution of ditridecylamine dissolved in isopropanol until the overall solution was weakly acidic. The resulting liquid was cooled to 10°C and filtered to obtain colorless crystals. The crystals were recrystallized twice with a mixed solvent of chloroform and n-hexane to obtain the target compound (compound 4: ditridecylammonium nitrate).

[0192] The obtained compound 4 1 The results of H-NMR spectra and infrared absorption spectra obtained by Fourier transform infrared spectroscopy (FT-IR) are shown below.

[0193] 1 H NMR (500MHz, CDCl3) δ (ppm): 8.760 (2H brs), 3.020-2.970 (4H m), 1.725 (4Hquintet / J=7.6Hz), 1.350-1.200 (m, 40H), 0.875 (6H t / J=7.0Hz)

[0194] FT-IRνmax(cm -1 ):3015,2958,2919,2853,1624,1470,1351

[0195] The elemental analysis results of compound 4 are shown below.

[0196] Calculated value (%) (C)26 H 56 N2O3): C, 70.22; H, 12.69; N, 6.30

[0197] Measured values ​​(%): C, 70.34; H, 12.80; N, 6.40

[0198] [Synthesis example 5]

[0199] Compound 5: Heptylidelammonium nitrate [C7H] 15 (C 10 H 21 )N + H2NO3 - ]

[0200] A solution was prepared by dissolving n-heptylamine and triethylamine (1.5 times the molar amount of n-heptylamine) in chloroform. Using a dropping funnel, a solution was prepared by adding a decanoyl chloride solution (equal in molar amount to n-heptylamine) dissolved in chloroform. After the addition was complete, the resulting chloroform solution was stirred at room temperature for 1 hour and then refluxed for 2 hours. The refluxed chloroform solution was cooled to room temperature and washed with water. Next, anhydrous sodium sulfate was added to the chloroform layer to remove water and solvent, yielding colorless crystals. The crystals were recrystallized using n-hexane to obtain N-heptyldecanoic acid amide (C9H). 19 CONHC7H 15 N-Heptyldecanoic acid amide and lithium aluminum hydride (LiAlH4) obtained above were added to anhydrous diethyl ether, refluxed for 2 hours, and then reacted at room temperature for 2 hours. After the reaction was completed, water was added to the resulting liquid to decompose the excess lithium aluminum hydride. Then, anhydrous sodium sulfate was added to the diethyl ether layer to remove water, and the solvent was removed to obtain crystals. The crystals were recrystallized twice with n-hexane to obtain heptyldecanoic acid. Then, a solution of concentrated nitric acid dissolved in isopropanol was added in small amounts each time to the solution obtained by dissolving heptyldecanoic acid in isopropanol until the overall solution was weakly acidic. The resulting liquid was cooled to 10°C and filtered to obtain colorless crystals. The crystals were recrystallized twice with a mixed solvent of chloroform and n-hexane to obtain the target compound (compound 5: heptyldecylammonium nitrate).

[0201] The obtained compound 5 1 The results of H-NMR spectra and infrared absorption spectra obtained by Fourier transform infrared spectroscopy (FT-IR) are shown below.

[0202] 1H NMR (500 MHz, CDC13) δ (ppm) : 8.773 (2H br s), 2.983 (4H quintet / J = 7.0 Hz), 1.703 (4H quintet / J = 7.4 Hz), 1.370-1.200 (m, 22H), 0.868 (3H t / J = 7.0 Hz), 0.862 (3H t / J = 7.0 Hz)

[0203] FT-IR vmaχ (cm -1 ): 2956, 2853, 1637, 1472, 1354

[0204] The elemental analysis results of the obtained compound 5 are shown below.

[0205] Calculated (%) (C 17 H 38 N2O3) : C, 64.11; H, 12.03; N, 8.80

[0206] Measured (%) : C, 64.53; H, 12.25; N, 8.68

[0207] [Synthesis Example 6]

[0208] Compound 6: Octyldecylammonium nitrate [C8H 17 (C 10 H 21 )N + H2NO3 - ]

[0209] To a solution in which n-octylamine and triethylamine in a molar amount 1.5 times the above octylamine were dissolved in chloroform, a solution in which decanoyl chloride in a molar amount equal to the above octylamine was dissolved in chloroform was added dropwise using a dropping funnel. After the dropwise addition was completed, the obtained chloroform solution was stirred at normal temperature for 1 hour and then heated to reflux for 2 hours. After the chloroform solution heated to reflux was cooled to normal temperature, it was washed with water. Next, anhydrous sodium sulfate was added to the chloroform layer, and after the water was removed, the solvent was removed to obtain a colorless crystal. The obtained crystal was recrystallized using n-hexane to obtain N-octyl decanamide (C9H 19 CONHC8H 17). To the N-octyldecanamide obtained by the above and lithium aluminum hydride (LiAlH4) in dry ether, refluxing was carried out for 2 hours and then reaction was carried out at normal temperature for 2 hours. After completion of the reaction, water was added to the obtained liquid to decompose the excess lithium aluminum hydride. Next, anhydrous sodium sulfate was added to the ether layer, and after removing the water, the solvent was removed to obtain crystals. The obtained crystals were recrystallized twice using n-hexane to obtain octyldecanamine. Next, to a solution in which octyldecanamine was dissolved in isopropyl alcohol, a solution in which concentrated nitric acid was dissolved in isopropyl alcohol was added little by little until the whole became weakly acidic. The obtained liquid was cooled to 10°C, and then 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).

[0210] The results of the elemental analysis of the obtained Compound 6 are shown below. 1 The results of H-NMR spectrum and infrared absorption spectrum by Fourier transform infrared spectroscopy (FT-IR) are shown below.

[0211] 1 H NMR (500 MHz, CDC13) δ (ppm) : 8.708 (2H brs), 3.010-2.960 (4H m), 1.710 (4H quintet / J = 7.2 Hz), 1.360-1.200 (m, 24H), 0.871 (3H t / J = 7.0 Hz), 0.864 (3H t / J = 7.0 Hz)

[0212] FT-IR vmaχ (cm -1 ): 2956, 2853, 1635, 1470, 1354

[0213] The results of the elemental analysis of the obtained Compound 6 are shown below.

[0214] Calculated value (%) (C 18 H 40 N2O3) : C, 65.02; H, 12.13; N, 8.42

[0215] Measured value (%) : C, 64.47; H, 12.13; N, 8.45

[0216] [Synthesis Example 7]

[0217] Compound 7: nonyldecylammonium nitrate [C9H 19 (C 10 H 21 )N + H2NO3 - ]

[0218] A solution was prepared by dissolving nonylamine and triethylamine (1.5 times the molar amount of nonylamine) in chloroform. Using a dropping funnel, a solution of decanoyl chloride (equal in molar amount to nonylamine) dissolved in chloroform was added dropwise. After the addition was complete, the resulting chloroform solution was stirred at room temperature for 1 hour and then refluxed for 2 hours. The refluxed chloroform solution was cooled to room temperature and washed with water. Next, anhydrous sodium sulfate was added to the chloroform layer to remove water and solvent, yielding colorless crystals. The crystals were recrystallized using hexane to obtain N-nonyldecanoamide (C9H2O). 19 CONHC9H 19 N-Nonyldecylamide and lithium aluminum hydride (LiAlH4) obtained above were added to anhydrous diethyl ether, refluxed for 2 hours, and then reacted at room temperature for 2 hours. After the reaction was completed, water was added to the resulting liquid to decompose the excess lithium aluminum hydride. Then, anhydrous sodium sulfate was added to the diethyl ether layer to remove water, and then the solvent was removed to obtain crystals. The crystals were recrystallized twice with n-hexane to obtain nonyldecylamine. Then, a solution of concentrated nitric acid dissolved in isopropanol was added in small amounts each time to the solution obtained by dissolving nonyldecylamine in isopropanol until the overall solution was weakly acidic. The resulting liquid was cooled to 10°C and filtered to obtain colorless crystals. The crystals were recrystallized twice with a mixed solvent of chloroform and n-hexane to obtain the target compound (compound 7: nonyldecylammonium nitrate).

[0219] The obtained compound 7 1 The results of H-NMR spectra and infrared absorption spectra obtained by Fourier transform infrared spectroscopy (FT-IR) are shown below.

[0220] 1 H NMR (500MHz, CDCl3) δ (ppm): 8.760 (2H brs), 3.100-2.970 (4H m), 1.703 (4Hquintet / J=7.0Hz), 1.360-1.200 (m, 26H), 0.872 (3H t / J=7.0Hz), 0.865 (3H t / J=7.0Hz)

[0221] FT-IRνmax(cm -1 ):2957,2853,1637,1470,1355

[0222] The elemental analysis results of compound 7 are shown below.

[0223] Calculated value (%) (C) 19 H 42N2O3): C, 65.84; H, 12.22; N, 8.08

[0224] Measured values ​​(%): C, 64.72; H, 12.21; N, 8.08

[0225] [Synthesis example 8]

[0226] Compound 8: Heptenyldodecylammonium nitrate [C7H] 15 (C 12 H 25 )N + H2NO3 - ]

[0227] A solution was prepared by dissolving n-heptylamine and triethylamine (1.5 times the molar amount of n-heptylamine) in chloroform. Using a dropping funnel, a solution was prepared by adding dodecanoic acid chloride (equal in molar amount to n-heptylamine) dissolved in chloroform. After the addition was complete, the resulting chloroform solution was stirred at room temperature for 1 hour and then refluxed for 2 hours. The refluxed chloroform solution was cooled to room temperature and washed with water. Next, anhydrous sodium sulfate was added to the chloroform layer to remove water and solvent, yielding colorless crystals. The crystals were recrystallized using n-hexane to obtain N-heptyldodecanoic acid chloride (C6H2O). 11 H 23 CONHC7H 15 N-Heptyldodecylamide and lithium aluminum hydride (LiAlH4) obtained above were added to anhydrous diethyl ether, refluxed for 2 hours, and then reacted at room temperature for 2 hours. After the reaction was completed, water was added to the resulting liquid to decompose the excess lithium aluminum hydride. Then, anhydrous sodium sulfate was added to the diethyl ether layer to remove water, and then the solvent was removed to obtain crystals. The crystals were recrystallized twice with n-hexane to obtain heptyldodecylamine. Then, a solution of concentrated nitric acid dissolved in isopropanol was added in small amounts each time to the solution obtained by dissolving heptyldodecylamine in isopropanol until the overall solution was weakly acidic. The resulting liquid was cooled to 10°C and filtered to obtain colorless crystals. The crystals were recrystallized twice with a mixed solvent of chloroform and n-hexane to obtain the target compound (compound 8: heptyldodecylammonium nitrate).

[0228] The obtained compound 8 1 The results of H-NMR spectra and infrared absorption spectra obtained by Fourier transform infrared spectroscopy (FT-IR) are shown below.

[0229] 1H NMR (500 MHz, CDC13) δ (ppm) : 8.697 (2H br s), 3.012-2.960 (4H m), 1.701 (4H quintet / J = 7.1 Hz), 1.370-1.200 (m, 26H), 0.872 (3H t / J = 7.0 Hz), 0.865 (3H t / J = 7.0 Hz)

[0230] FT-IR vmaχ (cm -1 ): 2957, 2852, 1636, 1470, 1354

[0231] The elemental analysis results of the obtained compound 8 are shown below.

[0232] Calculated (%) (C 19 H 42 N2O3) : C, 65.84; H, 12.22; N, 8.08

[0233] Measured (%) : C, 64.79; H, 13.19; N, 8.09

[0234] [Synthesis Example 9]

[0235] Compound 9: octyldodecylammonium nitrate [C8H 17 (C 12 H 25 )N + H2NO3 - ]

[0236] To a solution in which n-octylamine and triethylamine in a molar amount 1.5 times the above n-octylamine were dissolved in chloroform, a solution in which dodecanoyl chloride in a molar amount equal to the above octylamine was dissolved in chloroform was added dropwise using a dropping funnel. After the dropwise addition was completed, the obtained chloroform solution was stirred at normal temperature for 1 hour and then heated to reflux for 2 hours. After the chloroform solution heated to reflux was cooled to normal temperature, it was washed with water. Next, anhydrous sodium sulfate was added to the chloroform layer, and after the water was removed, the solvent was removed to obtain a colorless crystal. The obtained crystal was recrystallized using n-hexane to obtain N-octyldodecanamide (C 11 H 23 CONHC8H 17). To the N-octyldodecanamide obtained by the above and lithium aluminum hydride (LiAlH4) in dry ether, reflux was carried out for 2 hours and reaction was carried out at normal temperature for 2 hours. After completion of the reaction, water was added to the obtained liquid to decompose the excess lithium aluminum hydride. Next, anhydrous sodium sulfate was added to the ether layer, and after removing the water, the solvent was removed to obtain crystals. The obtained crystals were recrystallized twice using n-hexane to obtain octyldodecylamine. Next, to the solution in which octyldodecylamine was dissolved in isopropyl alcohol, a solution in which concentrated nitric acid was dissolved in isopropyl alcohol was added little by little until the whole became weakly acidic. The obtained liquid was cooled to 10°C, and then 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).

[0237] The results of the elemental analysis of the obtained Compound 9 are shown below. 1 The results of H-NMR spectrum and infrared absorption spectrum by Fourier transform infrared spectroscopy (FT-IR) are shown below.

[0238] 1 H NMR (500 MHz, CDC13) δ (ppm) : 8.766 (2H brs), 3.020-2.950 (4H m), 1.711 (4H quintet / J = 7.6 Hz), 1.370-1.210 (m, 28H), 0.870 (6H t / J = 7.0 Hz), 0.864 (3H t / J = 7.0 Hz)

[0239] FT-IR vmaχ (cm -1 ): 2956, 2853, 1635, 1470, 1355

[0240] The results of the elemental analysis of the obtained Compound 9 are shown below.

[0241] Calculated value (%) (C 20 H 44 N2O3) : C, 66.62; H, 12.30; N, 7.77

[0242] Measured value (%) : C, 66.60; H, 12.46; N, 7.79

[0243] [Synthesis Example 10]

[0244] Compound 10: nonyldodecylammonium nitrate [C9H 19 (C 12 H 25 )N + H2NO3 - ]

[0245] To a solution in which n-nonylamine and triethylamine in an amount 1.5 times the molar amount of the above n-nonylamine were dissolved in chloroform, a solution in which dodecanoyl chloride (Do decanoic acid chloride) in an amount equal to the above n-nonylamine was dissolved in chloroform was added dropwise using a dropping funnel. After the dropwise addition was completed, the resulting chloroform solution was stirred at normal temperature for 1 hour and then heated to reflux for 2 hours. After the chloroform solution heated to reflux was cooled to normal temperature, it was washed with water. Next, anhydrous sodium sulfate was added to the chloroform layer, and after the water was removed, the solvent was removed to obtain a colorless crystal. The obtained crystal was recrystallized using a mixed solvent of chloroform and n-hexane to obtain N-nonyldodecanamide (C 11 H 23 CONHC9H 19 To anhydrous diethyl ether, N-nonyldodecanamide obtained by the above and lithium aluminum hydride (LiAlH4) were added, and after refluxing for 2 hours, reaction was performed at room temperature for 2 hours. After the reaction was completed, water was added to the obtained liquid to decompose the excess lithium aluminum hydride. Next, anhydrous sodium sulfate was added to the diethyl ether layer, and after the water was removed, the solvent was removed to obtain a crystal. The obtained crystal was recrystallized twice using n-hexane to obtain nonyldodecanamine. Next, to a solution in which nonyldodecanamine was dissolved in isopropyl alcohol, a solution in which concentrated nitric acid was dissolved in isopropyl alcohol was added little by little until the whole became weakly acidic. After the obtained liquid was cooled to 10°C, it was filtered to thereby obtain a colorless crystal. The obtained crystal was recrystallized twice using a mixed solvent of chloroform and n-hexane to obtain the target compound (Compound 10: nonyldodecylammonium nitrate).

[0246] The results of the H-NMR spectrum and the infrared absorption spectrum by Fourier transform infrared spectroscopy (FT-IR) of the obtained Compound 10 are shown below. 1 H-NMR spectrum and the infrared absorption spectrum by Fourier transform infrared spectroscopy (FT-IR) of the obtained Compound 10 are shown below.

[0247] 1 H NMR (500 MHz, CDC13) δ (ppm): 8.675 (2H, brs), 3.010-2.950 (4H, m), 1.725 (4H, quintet / J = 7.6 Hz), 1.360-1.200 (m, 30H), 0.875 (3H, t / J = 7.0 Hz), 0.871 (3H, t / J = 7.0 Hz)

[0248] FT-IR v max (cm -1 ): 2957, 2853, 1637, 1470, 1353

[0249] The elemental analysis results of the obtained Compound 10 are shown below.

[0250] Calculated value (%) (C) 21 H 46 N2O3): C, 67.33; H, 12.38; N, 7.48

[0251] Measured values ​​(%): C, 67.54; H, 12.45; N, 7.50

[0252] [Comparative Synthesis Example 1]

[0253] Comparative compound 1: Dihexylammonium nitrate [(C6H] 13 )2N + H2NO3 - ]

[0254] A solution of dihexylamine dissolved in isopropanol was prepared by adding small amounts of concentrated nitric acid dissolved in isopropanol each time until the overall solution was weakly acidic. The resulting liquid was cooled to 10°C and filtered to obtain colorless crystals. The crystals were recrystallized twice using a mixed solvent of hexane and ethanol to obtain the target compound (Comparative Compound 1: dihexylammonium nitrate).

[0255] The obtained comparison compound 1 1 The results of H-NMR spectra and infrared absorption spectra obtained by Fourier transform infrared spectroscopy (FT-IR) are shown below.

[0256] 1 H NMR (500MHz, CDCl3) δ (ppm): 8.782 (2H brs), 2.991 (4H br quintet / J = 7.5Hz), 1.704 (4H quintet / J = 7.5Hz), 1.370-1.210 (m, 12H), 0.863 (6H t / J = 7.0Hz)

[0257] FT-IRνmax(cm -1 ):3017,2918,2853,1622,1472,1351

[0258] The elemental analysis results of the comparative compound 1 are shown below.

[0259] Calculated value (%) (C) 12 H 28 N2O3): C, 58.03; H, 11.36; N, 11.28

[0260] Measured values ​​(%): C, 58.03; H, 11.42; N, 11.38

[0261] [Comparative Synthesis Example 2]

[0262] Comparative Compound 2: dioctylammonium nitrate [(C8H 17 )2N + H2NO3 - ]

[0263] To a solution in which dioctylamine was dissolved in isopropyl alcohol, a solution in which concentrated nitric acid was dissolved in isopropyl alcohol was added little by little until the whole became weakly acidic. After the resulting liquid was cooled to 10°C, it was filtered, whereby colorless crystals were obtained. The obtained crystals were recrystallized twice using ethanol, whereby the target compound (Comparative Compound 2: dioctylammonium nitrate) was obtained.

[0264] The results of the H-NMR spectrum and the infrared absorption spectrum by Fourier transform infrared spectroscopy (FT-IR) of the obtained Comparative Compound 2 are shown below. 1 H-NMR spectrum and the infrared absorption spectrum by Fourier transform infrared spectroscopy (FT-IR) of the obtained Comparative Compound 2 are shown below.

[0265] 1 H NMR (500 MHz, CDC13) δ (ppm): 8.748 (2H brs), 3.020-2.900 (4H m), 1.716 (4H quintet / J = 7.6 Hz), 1.370-1.100 (m, 20H), 0.873 (6H t / J = 6.8 Hz)

[0266] FT-IR vmaχ (cm -1 ): 3018, 2917, 2853, 1623, 1472, 1351

[0267] The results of the elemental analysis of the obtained Comparative Compound 2 are shown below.

[0268] Calculated (%) (C 16 H 36 N2O3): C, 63.12; H, 11.92; N, 9.20

[0269] Measured values (%): C, 63.37; H, 12.00; N, 9.28

[0270] [Comparative Synthesis Example 3]

[0271] Comparative Compound 3: didecylammonium nitrate [(C 10 H 21 )2N + H2NO3 - ]

[0272] A solution of didecylamine dissolved in isopropanol was prepared by adding small amounts of concentrated nitric acid dissolved in isopropanol each time until the overall solution was weakly acidic. The resulting liquid was cooled to 10°C and filtered to obtain colorless crystals. The crystals were recrystallized twice with ethanol to obtain the target compound (comparative compound 3: didecylammonium nitrate).

[0273] The obtained comparison compound 3 1 The results of H-NMR spectra and infrared absorption spectra obtained by Fourier transform infrared spectroscopy (FT-IR) are shown below.

[0274] 1 H NMR (500MHz, CDCl3) δ (ppm): 8.774 (2H brs), 3.01-2.90 (4H m), 1.705 (4Hquintet / J=7.0Hz), 1.350-1.170 (m, 28H), 0.874 (6H t / J=7.0Hz)

[0275] FT-IRνmax(cm -1 ):3010,2918,2853,1624,1472,1353

[0276] The elemental analysis results of the comparative compound 3 are shown below.

[0277] Calculated value (%) (C) 20 H 44 N2O3): C, 66.62; H, 12.30; N, 7.77

[0278] Measured values ​​(%): C, 66.94; H, 12.51; N, 7.84

[0279] [Comparative Synthesis Example 4]

[0280] Comparative compound 4: Didodecylammonium nitrate [(C 12 H 25 )2N + H2NO3 - ]

[0281] A solution of didodecylamine dissolved in isopropanol was prepared by adding small amounts of concentrated nitric acid dissolved in isopropanol each time until the overall solution was weakly acidic. The resulting liquid was cooled to 10°C and filtered to obtain colorless crystals. The crystals were recrystallized twice with ethanol to obtain the target compound (comparative compound 4: didodecylamine nitrate).

[0282] The obtained comparison compound 4 1The results of H-NMR spectrum and infrared absorption spectrum by Fourier transform infrared spectroscopy (FT-IR) are shown below.

[0283] 1 H NMR (500 MHz, CDC13) δ (ppm): 8.772 (2H br s), 3.00-2.91 (4H m), 1.75-1.63 (4H m), 1.40-1.10 (m, 36H), 0.863 (6H t / J = 7.0 Hz)

[0284] FT-IR vmaχ (cm -1 ): 3011, 2919, 2852, 1623, 1470, 1351

[0285] The results of elemental analysis of the obtained comparative compound 4 are shown below.

[0286] Calculated (%) (C 24 H 52 N2O3): C, 69.18; H, 12.58; N, 6.72

[0287] Measured (%): C, 69.49; H, 12.80; N, 6.74

[0288] [Comparative Synthesis Example 5]

[0289] Comparative compound 5: Tetradecylammonium nitrate [(C 14 H 29 )2N + H2NO3 - ]

[0290] To a solution in which tetradecylamine and triethylamine in a molar amount 1.5 times that of the above tetradecylamine were dissolved in chloroform, a solution in which tetradecanoic acid chloride in a molar amount equal to that of the above tetradecylamine was dissolved in chloroform was added dropwise using a dropping funnel. After the dropwise addition was completed, the resulting chloroform solution was stirred at normal temperature for 1 hour and then heated to reflux for 2 hours. After the chloroform solution heated to reflux was cooled to normal temperature, it was washed with water. Next, anhydrous sodium sulfate was added to the chloroform layer, and after the water was removed, the solvent was removed to obtain a colorless crystal. The obtained crystal was recrystallized using a mixed solvent of chloroform and n-hexane to obtain N-tetradecyltetradecanamide (C 13 H 27 CONHC 14 H 29). To the N-tetradecyl tetradecanamide obtained by the above and lithium aluminum hydride (LiAlH4) in dry ether, reflux was carried out for 2 hours and reaction was carried out at normal temperature for 2 hours. After completion of the reaction, water was added to the obtained liquid to decompose the excess lithium aluminum hydride. Next, anhydrous sodium sulfate was added to the ether layer, and after removing the water, the solvent was removed to obtain crystals. The obtained crystals were recrystallized twice using n-hexane to obtain ditetradecylamine. Next, to the solution in which ditetradecylamine was dissolved in isopropyl alcohol, a solution in which concentrated nitric acid was dissolved in isopropyl alcohol was added little by little until the whole became weakly acidic. The obtained liquid was cooled to 10°C, and then filtered to obtain colorless crystals. The obtained crystals were recrystallized twice using ethanol to obtain the target compound (Comparative Compound 5: ditetradecylammonium nitrate).

[0291] The results of the H-NMR spectrum and infrared absorption spectrum by Fourier transform infrared spectroscopy (FT-IR) of the obtained Comparative Compound 5 are shown below. 1 H-NMR spectrum and infrared absorption spectrum by Fourier transform infrared spectroscopy (FT-IR) of the obtained Comparative Compound 5 are shown below.

[0292] 1 H NMR (500 MHz, CDC13) δ (ppm) : 8.766 (2H brs), 2.972 (4H m), 1.716 (4H quintet / J = 7.6 Hz), 1.322-1.204 (m, 44H), 0.875 (6H t / J = 7.0 Hz)

[0293] FT-IR vmaχ (cm -1 ): 3015, 2919, 2853, 1623, 1473, 1350

[0294] The results of the elemental analysis of the obtained Comparative Compound 5 are shown below.

[0295] Calculated (%) (C 28 H 60 N2O3) : C, 71.13; H, 12.79; N, 5.93

[0296] Measured (%) : C, 72.39; H, 13.20; N, 5.55

[0297] [Synthesis of bisalkylammonium chlorate]

[0298] [Synthesis Example 11]

[0299] Compound 11: bisnonylammonium chlorate [(C9H 19 )2N + H2ClO3 - ]

[0300] To the solution obtained by dissolving n-nonylamine and triethylamine in an amount 1.5 times the molar amount of the above n-nonylamine in chloroform, a solution obtained by dissolving nonanoic acid chloride in an amount equal to the above n-nonylamine in chloroform was added dropwise using a dropping funnel. After the completion of the dropwise addition, the resulting chloroform solution was stirred at normal temperature for 1 hour and then heated under reflux for 2 hours. After the chloroform solution heated under reflux was cooled to normal temperature, it was washed with water. Next, anhydrous sodium sulfate was added to the chloroform layer, and after the removal of water, the solvent was removed to obtain a colorless crystal. The obtained crystal was recrystallized using a mixed solvent of chloroform and n-hexane to obtain N-nonyl nonanamide (C8H 17 CONHC9H 19 ) in an amount of 1.5 g. To anhydrous diethyl ether, N-nonyl nonanamide obtained by the above and lithium aluminum hydride (LiAlH4) were added, and after refluxing for 2 hours, the reaction was carried out at room temperature for 2 hours. After the completion of the reaction, water was added to the obtained liquid to decompose the excess lithium aluminum hydride. Next, anhydrous sodium sulfate was added to the diethyl ether layer, and after the removal of water, the solvent was removed to obtain a crystal. The obtained crystal was recrystallized twice using n-hexane to obtain bis-n-nonylamine. Next, to the solution obtained by dissolving bis-n-nonylamine in isopropyl alcohol, a solution obtained by dissolving chloric acid in an amount of 60 mass% in isopropyl alcohol was added little by little until the whole became weakly acidic. After the obtained liquid was cooled to 10°C, it was filtered to obtain a colorless crystal. The obtained crystal was recrystallized twice using isopropyl alcohol to obtain the target compound (Compound 11: bisnonylammonium chlorate).

[0301] The results of the H-NMR spectrum of the obtained Compound 11 were as shown below. 1 H-NMR spectrum of the obtained Compound 11 were as shown below.

[0302] 1 H NMR (500 MHz, CDC13) δ (ppm): 6.931 (2H brs), 3.070 (4H quintet / J = 3.9 Hz), 1.778 (4H quintet / J = 7.6 Hz), 1.390-1.210 (m, 24H), 0.874 (6H t / J = 7.0 Hz)

[0303] [Synthesis Example 12]

[0304] Compound 12: bisundecylammonium chlorate [(C 11 H 23 )2N + H2ClO3 - ]

[0305] To obtain a solution in which undecylamine and triethylamine (1.5 times the molar amount of undecylamine) are dissolved in chloroform, an equal molar amount of undecanoic acid chloride (dissolved in chloroform) is added dropwise using a dropping funnel. After the addition is complete, the resulting chloroform solution is stirred at room temperature for 1 hour and then heated under reflux for 2 hours. The refluxed chloroform solution is cooled to room temperature and washed with water. Next, anhydrous sodium sulfate is added to the chloroform layer to remove water, and then the solvent is removed to obtain colorless crystals. The obtained crystals are recrystallized using a mixed solvent of chloroform and n-hexane to obtain N-undecylundecylamide (C 10 H 21 CONHC 11 H 23 The N-undecylundecylamide and lithium aluminum hydride (LiAlH4) obtained above were added to anhydrous diethyl ether, refluxed for 2 hours, and then reacted at room temperature for 2 hours. After the reaction was completed, water was added to the resulting liquid to decompose the excess lithium aluminum hydride. Then, anhydrous sodium sulfate was added to the diethyl ether layer to remove water, and then the solvent was removed to obtain crystals. The crystals were recrystallized twice with n-hexane to obtain bis-undecylamine. Next, a solution of bis-undecylamine dissolved in isopropanol was added in small amounts each time to a solution of 60% by mass chloric acid dissolved in isopropanol until the overall solution was weakly acidic. The resulting liquid was cooled to 10°C and filtered to obtain colorless crystals. The crystals were recrystallized twice with isopropanol to obtain the target compound (compound 12: bis-undecylammonium chlorate).

[0306] The obtained compound 12 1 The results of the H-NMR spectra are shown below.

[0307] 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)

[0308] [Comparative Synthesis Example 6]

[0309] Comparative compound 6: Didecylamine chlorate ammonium salt [(C 10 H 21 )2N + H2ClO3 - ]

[0310] Didecylamine was dissolved in isopropanol to obtain a didecylamine isopropanol solution. To the obtained didecylamine isopropanol solution, a solution in which 60 mass% chloric acid was dissolved in isopropanol was gradually added in small amounts until the whole became slightly acidic. After the obtained liquid was cooled to 10°C, it was filtered to obtain colorless crystals. The obtained crystals were recrystallized twice using isopropanol to obtain the target compound (Comparative Compound 6: didecylammonium chloric acid salt).

[0311] The obtained Comparative Compound 6 had 1 The results of H-NMR spectrum are shown below.

[0312] 1 H NMR (500 MHz, CDC13) δ (ppm): 6.918 (2H brs), 3.073 (4H quintet / J = 5.4 Hz), 1.775 (4H quintet / J = 7.0 Hz), 1.396-1.190 (m, 28H), 0.874 (6H t / J = 7.0 Hz)

[0313] [Synthesis of bisalkylammonium nitrate]

[0314] [Synthesis Example 13]

[0315] Compound 13: decylundecylammonium nitrate [C 10 H 21 (C 11 H 23 )N + H2NO3 - ]

[0316] To a solution in which undecylamine and triethylamine in a molar amount 1.5 times that of the above undecylamine were dissolved in chloroform, a solution in which capryloyl chloride in a molar amount equivalent to the above undecylamine was dissolved in chloroform was added dropwise using a dropping funnel. After the dropwise addition was completed, the obtained chloroform solution was stirred at normal temperature for 1 hour and then heated to reflux for 2 hours. After the chloroform solution heated to reflux was cooled to normal temperature, it was washed with water. Next, anhydrous sodium sulfate was added to the chloroform layer, moisture was removed, and then the solvent was removed to obtain colorless crystals. The obtained crystals were recrystallized using a mixed solvent of chloroform and n-hexane to obtain N-undecylcaprylamide (C9H 19 CONHC 11 H 23). To the N-undecyl decanamide obtained by the above and lithium aluminum hydride (LiAlH4) was added anhydrous diethyl ether, and refluxed for 2 hours and reacted at normal temperature for 2 hours. After the reaction was completed, water was added to the obtained liquid to decompose the excess lithium aluminum hydride. Next, anhydrous sodium sulfate was added to the diethyl ether layer, and after the water was removed, the solvent was removed to obtain crystals. The obtained crystals were dissolved by heating in n-hexane, and then cooled, filtered, and the precipitated N-undecyl decanamide was removed. The filtrate was concentrated to obtain decylundecylamine. Next, to the solution in which decylundecylamine was dissolved in isopropyl alcohol, a solution in which concentrated nitric acid was dissolved in isopropyl alcohol was added in small amounts each time until the whole became weakly acidic. The obtained liquid was cooled to 10°C, and then filtered to obtain colorless crystals. The obtained crystals were recrystallized twice using n-hexane to obtain the target compound (Compound 13: decylundecylammonium nitrate).

[0317] The results of the H-NMR spectrum and infrared absorption spectrum by Fourier transform infrared spectroscopy (FT-IR) of the obtained Compound 13 are shown below. 1 The results of the H-NMR spectrum and infrared absorption spectrum by Fourier transform infrared spectroscopy (FT-IR) of the obtained Compound 13 are shown below.

[0318] 1 H NMR (500 MHz, CDC13) δ (ppm) : 8.720 (2H, br s), 3.014-2.957 (4H, m), 1.721-1.660 (4H, m), 1.360-1.200 (m, 30H), 0.869 (6H, t / J = 7.0 Hz)

[0319] FT-IR vmaχ (cm -1 ): 2957, 2855, 1637, 1472, 1354

[0320] [Synthesis Example 14]

[0321] Compound 14: decylundecylammonium nitrate [C 11 H 23 (C 12 H 25 )N + H2NO3 - ]

[0322] A solution was prepared by dissolving dodecyl primary amine and triethylamine (1.5 times the molar amount of dodecyl primary amine) in chloroform. Using a dropping funnel, an equal molar amount of undecyl chloride was added dropwise to a solution prepared by dissolving undecyl chloride in chloroform. After the addition was complete, the resulting chloroform solution was stirred at room temperature for 1 hour and then refluxed for 2 hours. The refluxed chloroform solution was cooled to room temperature and washed with water. Next, anhydrous sodium sulfate was added to the chloroform layer to remove water, and then the solvent was removed to obtain colorless crystals. The obtained crystals were recrystallized using a mixed solvent of chloroform and n-hexane to obtain N-dodecylundecylamide (C... 10 H 21 CONHC 12 H 25 N-dodecyl undecylamide and lithium aluminum hydride (LiAlH4) obtained above were added to anhydrous diethyl ether, refluxed for 2 hours, and then reacted at room temperature for 2 hours. After the reaction was completed, water was added to the resulting liquid to decompose the excess lithium aluminum hydride. Then, anhydrous sodium sulfate was added to the diethyl ether layer to remove water and solvent, resulting in crystals. The crystals were dissolved in n-hexane by heating, cooled, filtered, and the precipitated N-dodecyl undecylamide was removed. The filtrate was concentrated to obtain undecyldodecylamine. Then, a solution of concentrated nitric acid dissolved in isopropanol was added in small amounts each time to the solution obtained by dissolving undecyldodecylamine in isopropanol until the overall solution was weakly acidic. The resulting liquid was cooled to 10°C and filtered to obtain colorless crystals. The crystals were recrystallized twice with n-hexane to obtain the target compound (compound 14: undecyldodecylammonium nitrate).

[0323] The obtained compound 14 1 The results of H-NMR spectra and infrared absorption spectra obtained by Fourier transform infrared spectroscopy (FT-IR) are shown below.

[0324] 1 H NMR (500MHz, CDCl3) δ (ppm): 8.727 (2H, brs), 3.011-2.954 (4H, m), 1.737-1.67 6(4H,m),1.360-1.200(m,34H),0.874(3H,t / J=7.0Hz),0.874(3H,t / J=7.0Hz)

[0325] FT-IRνmax(cm -1 ):2958,2853,1638,1472,1352

[0326] [Synthesis Example 15]

[0327] Compound 15: Undecyltridecylammonium nitrate [C 11 H 23 (C 13 H 27 )N + H2NO3 - ]

[0328] A solution was prepared by dissolving tridecylamine and triethylamine (1.5 times the molar amount of tridecylamine) in chloroform. Using a dropping funnel, an equal molar amount of undecylyl chloride was added dropwise to the same solution dissolved in chloroform. After the addition was complete, the resulting chloroform solution was stirred at room temperature for 1 hour and then refluxed for 2 hours. The refluxed chloroform solution was cooled to room temperature and washed with water. Next, anhydrous sodium sulfate was added to the chloroform layer to remove water, and then the solvent was removed to obtain colorless crystals. The obtained crystals were recrystallized using a mixed solvent of chloroform and n-hexane to obtain N-tridecylundecylamide (C... 10 H 21 CONHC 13 H 27 N-Tetrazylundecylamide and lithium aluminum hydride (LiAlH4) obtained above were added to anhydrous diethyl ether, refluxed for 2 hours, and then reacted at room temperature for 2 hours. After the reaction was completed, water was added to the resulting liquid to decompose the excess lithium aluminum hydride. Then, anhydrous sodium sulfate was added to the diethyl ether layer to remove water and solvent, resulting in crystals. The crystals were dissolved in n-hexane by heating, cooled, filtered, and the precipitated N-tetrazylundecylamide was removed. The filtrate was concentrated to obtain undecyltridecylamine. Then, a solution of concentrated nitric acid dissolved in isopropanol was added in small amounts each time to the solution obtained by dissolving undecyltridecylamine in isopropanol until the overall solution was weakly acidic. The resulting liquid was cooled to 10°C and filtered to obtain colorless crystals. The crystals were recrystallized twice with n-hexane to obtain the target compound (compound 15: undecyltridecylammonium nitrate).

[0329] The obtained compound 15 1 The results of H-NMR spectra and infrared absorption spectra obtained by Fourier transform infrared spectroscopy (FT-IR) are shown below.

[0330] 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)

[0331] FT-IRνmax(cm -1 ):2957,2854,1638,1471,1353

[0332] [Synthesis Example 16]

[0333] Compound 16: Undecyltetradecylammonium nitrate [C 11 H 23 (C 14 H 29 )N + H2NO3 - ]

[0334] A solution was prepared by dissolving tetradecylamine and triethylamine (1.5 times the molar amount of tetradecylamine) in chloroform. Using a dropping funnel, an equal molar amount of undecyl chloride was added dropwise to the same solution dissolved in chloroform. After the addition was complete, the resulting chloroform solution was stirred at room temperature for 1 hour and then refluxed for 2 hours. The refluxed chloroform solution was cooled to room temperature and washed with water. Next, anhydrous sodium sulfate was added to the chloroform layer to remove water, and then the solvent was removed to obtain colorless crystals. The obtained crystals were recrystallized using a mixed solvent of chloroform and n-hexane to obtain N-tetradecylundecylamide (C... 10 H 21 CONHC 14 H 29 N-Tetradecyl undecylamide and lithium aluminum hydride (LiAlH4) obtained above were added to anhydrous diethyl ether, refluxed for 2 hours, and then reacted at room temperature for 2 hours. After the reaction was completed, water was added to the resulting liquid to decompose the excess lithium aluminum hydride. Then, anhydrous sodium sulfate was added to the diethyl ether layer to remove water and solvent, resulting in crystals. The crystals were dissolved in n-hexane by heating, cooled, filtered, and the precipitated N-tetradecyl undecylamide was removed. The filtrate was concentrated to obtain undecyltetradecylamine. Then, a solution of concentrated nitric acid dissolved in isopropanol was added in small amounts each time to the solution obtained by dissolving undecyltetradecylamine in isopropanol until the overall solution was weakly acidic. The resulting liquid was cooled to 10°C and filtered to obtain colorless crystals. The crystals were recrystallized twice with n-hexane to obtain the target compound (compound 16: undecyltetradecylammonium nitrate).

[0335] The obtained compound 16 1 The results of H-NMR spectra and infrared absorption spectra obtained by Fourier transform infrared spectroscopy (FT-IR) are shown below.

[0336] 1H NMR (500 MHz, CDC13) δ (ppm): 8.734 (2H, br s), 3.009-2.954 (4H, m), 1.739-1.679 (4H, m), 1.370-1.194 (m, 38H), 0.879 (3H, t / J = 7.0 Hz), 0.876 (3H, t / J = 7.0 Hz)

[0337] FT-IR vmaχ (cm -1 ): 2958, 2854, 1636, 1471, 1354

[0338] [Assessment]

[0339] (Examples 1 to 16 and Comparative Examples 1 to 6)

[0340] For the compounds 1 to 16 synthesized in Synthesis Examples 1 to 16, and the comparative compounds 1 to 6 synthesized in Comparative Synthesis Examples 1 to 6, measurement of phase transition temperature (unit: °C) and latent heat amount (unit: J / g), confirmation of presence or absence of repetition property, and confirmation of whether or not the phase transition is solid phase-solid phase phase transition were performed. The results are shown in Tables 1 to 6 and Figures 1-5

[0341] The phase transition temperature and the latent heat amount were measured using a differential scanning calorimeter [Model: DSC3200] manufactured by MacScience Co., Ltd. as a measuring device, under the following conditions. In addition, the phase transition temperature is the temperature of the endothermic peak at the time of temperature increase, and the latent heat amount is the heat amount of the endothermic peak at the time of temperature increase.

[0342] The presence or absence of the repetition property was judged by whether or not heat generation occurs at the time of cooling. Specifically, if no heat generation occurs when cooled to 30°C in about 1 hour after heating to 100°C, it was judged that the repetition property is not present.

[0343] Whether or not the phase transition is solid phase-solid phase phase transition was judged based on whether or not melting occurs before and after the phase transition. Specifically, if there is no melting before and after the phase transition, it was judged that the phase transition is solid phase-solid phase phase transition.

[0344] -Conditions-

[0345] Measurement temperature range: 30°C to 100°C

[0346] Temperature increase rate: 10°C / min

[0347] Atmosphere gas: air

[0348] Measurement sample amount: 6.0 mg

[0349] [Table 1]

[0350] [Table 2]

[0351] [Table 2]

[0352]

[0353] 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.

[0354] Examples 1-4 and Comparative Examples 1-5 are all dialkylammonium nitrates with the same number of carbons n and m in chemical formula (I). The difference between Examples 1-4 and Comparative Examples 1-5 is that the former have odd numbers of carbons n and m, while the latter have even numbers of carbons n and m.

[0355] In Examples 1-4 and Comparative Examples 1-5, it was confirmed that there was no melting before and after the phase transition, and the phase transition was a solid-to-solid phase transition.

[0356] As shown in Table 1, it can be seen that in Examples 1 to 4, the phase transition temperature is as low as below 60°C, the latent heat is large, and the characteristics are repeatable.

[0357] On the other hand, as shown in Table 2, it can be seen that the latent heat in Comparative Example 1 is significantly small and does not exhibit repeatable characteristics. It can be seen that Comparative Example 2 has a relatively large latent heat at low phase transition temperatures but does not exhibit repeatable characteristics. Specifically, in Comparative Examples 1 and 2, no heat is generated during cooling, even...

[0358] Subsequent heating did not show the same endothermic effect as before. This indicates that the phase transition temperature in Comparative Examples 3-5 exceeded 60°C.

[0359] The latent heat of Examples 1-4 and Comparative Examples 1-5 is as follows: Figure 1 As shown.

[0360] Depend on Figure 1 It can be seen that, in the case of dialkylammonium nitrates with the same carbon number n and m in chemical formula (I), the latent heat of Examples 1 to 4 with odd carbon number n and m is significantly greater than that of Comparative Examples 1 to 5 with even carbon number n and m.

[0361] From Table 1 and Table 2 and Figure 1 The results show that dialkylammonium nitrates with the same odd number of carbons n and m in formula (I) maintain the phase transition temperature at a lower level below 60°C and have significantly larger latent heat compared to dialkylammonium nitrates with the same even number of carbons n and m in formula (I).

[0362] [Table 3]

[0363]

[0364] [Table 4]

[0365]

[0366] The results of Examples 5-7 are shown in Table 3 and Figure 2 As shown, the results of Examples 8-10 are presented in Table 4 and Figure 3 As shown. Additionally, Table 3 and... Figure 2 Comparative Example 3 described herein is for comparison with Examples 5-7 and is the same as Comparative Example 3 described in Table 2 above. Table 4 and Figure 3 Comparative Example 4 described herein is for comparison with Examples 8 to 10 and is the same as Comparative Example 4 described in Table 2 above.

[0367] In Examples 5-10, the dialkylammonium nitrates with different values ​​of carbon number n and m in chemical formula (I) were used. In contrast, in Comparative Examples 3 and 4, the dialkylammonium nitrates with the same even value of carbon number n and m in chemical formula (I) were used.

[0368] In Examples 5 to 10, it was confirmed that there was no melting before and after the phase transition, and the phase transition was a solid-to-solid phase transition.

[0369] As shown in Tables 3 and 4, it can be seen that in Examples 5 to 10, the phase transition temperature is as low as below 60°C, the latent heat is high, and the characteristics are repeatable.

[0370] Depend on Figure 2 It can be seen that in Examples 5-7, a large latent heat is ensured, and a lower phase transition temperature is observed compared to Comparative Example 3. Furthermore, from Figure 3 It can be seen that in Examples 8 to 10, a large latent heat is ensured, and a lower phase transition temperature is shown compared to Comparative Example 4.

[0371] From Tables 3 and 4 and Figure 2 and Figure 3 The results show that dialkylammonium nitrates with different carbon numbers in chemical formula (I) have greater latent heat at lower phase transition temperatures compared to dialkylammonium nitrates with the same and even carbon number in chemical formula (I).

[0372] [Table 5]

[0373]

[0374] The results of Examples 11 and 12, and Comparative Example 6 are shown in Table 5 and... Figure 4 As shown.

[0375] Examples 11 and 12, as well as Comparative Example 6, are all dialkylammonium chlorates with the same number of carbons n and m in chemical formula (I). The difference between Examples 11 and 12 and Comparative Example 6 is that the former has odd numbers of carbons n and m, while the latter has even numbers of carbons n and m.

[0376] In both Examples 11 and 12, it was confirmed that there was no melting before and after the phase transition, and the phase transition was a solid-to-solid phase transition.

[0377] As shown in Table 5, it can be seen that in Examples 11 and 12, the phase transition temperature is as low as 60°C or below, the latent heat is large, and the characteristics are repeatable. On the other hand, it can be seen that in Comparative Example 6, although the phase transition temperature is below 60°C, the latent heat is significantly small.

[0378] Depend on Figure 4 It can be seen that the latent heat of Examples 11 and 12 is significantly greater than that of Comparative Example 6.

[0379] From Table 5 and Figure 4 The results show that dialkylammonium chlorates with the same odd number of carbons n and m in formula (I) maintain the phase transition temperature below 60°C and have significantly larger latent heat compared to dialkylammonium chlorates with the same even number of carbons n and m in formula (I).

[0380] From the above, it can be seen that in compounds represented by chemical formula (I), namely dialkylammonium compounds, not only nitrates but also chlorates, when the number of carbons n and m (i.e., the number of carbons in the alkyl chain) in chemical formula (I) are the same, the latent heat is greater when the odd values ​​are greater than when the even values ​​are greater. These results can be considered to suggest that regardless of X in chemical formula (I)... - Regardless of the type, the same effect can be achieved.

[0381] [Table 6]

[0382]

[0383] The DSC-based thermal analysis results of Examples 13-16 are shown in Table 6. Furthermore, Comparative Example 3 in Table 6 is recorded for comparison with Example 13 and is the same as Comparative Example 3 recorded in Table 2 above; Comparative Example 4 in Table 6 is recorded for comparison with Example 14 and is the same as Comparative Example 4 recorded in Table 2 above; Comparative Example 5 in Table 6 is recorded for comparison with Example 16 and is the same as Comparative Example 5 recorded in Table 2 above.

[0384] In Examples 13-16, the carbon numbers n and m in chemical formula (I) are different values ​​for dialkylammonium nitrates.

[0385] In each of Examples 13 to 16, it was confirmed that there was no melting before and after the phase change, and the phase change was a solid phase-solid phase phase change.

[0386] As shown in Table 6, it was found that in each of Examples 13 to 16, the phase change temperature was as low as 60°C or lower, the latent heat amount was high, and the repeat characteristics were excellent.

[0387] From the results shown in Table 6, it was found that the dialkylammonium nitrate salt of Chemical Formula (I) in which the carbon numbers n and m were different values had a larger latent heat amount at a lower phase change temperature than the dialkylammonium nitrate salt in which the carbon numbers were the same and even values.

[0388] Measurement of X-ray Diffraction Spectra

[0389] As the measuring device, a SmartLab 9kW manufactured by Rigaku Corporation was used to measure the X-ray diffraction spectra of the powder state of the above-mentioned compound 2 at 26°C and at 70°C after heating the sample holder. The X-ray diffraction spectra of compound 2 before and after the phase change are shown in FIG. 6. As shown in FIG. 6, it was found that there was a peak indicating a crystal structure at the temperature before the phase change, and there was a peak indicating an amorphous state after the phase change. In addition, it was confirmed that by cooling compound 2 at room temperature for 2 hours, the crystal structure was recovered. This suggests that the phase change of compound 2 is a crystal→amorphous phase, i.e., a solid phase-solid phase phase change, and the compounds of the series of examples have excellent repeat characteristics in the phase change. Figure 5 Figure 5 As shown in FIG. 6, it was found that there was a peak indicating a crystal structure at the temperature before the phase change, and there was a peak indicating an amorphous state after the phase change. In addition, it was confirmed that by cooling compound 2 at room temperature for 2 hours, the crystal structure was recovered. This suggests that the phase change of compound 2 is a crystal→amorphous phase, i.e., a solid phase-solid phase phase change, and the compounds of the series of examples have excellent repeat characteristics in the phase change.​

Claims

1. A latent heat storage material, comprising a compound represented by the following formula (I); [Chemical Formula 1] In the chemical formula (I), as for n and m, n represents 7, 11 or 13 in the case of n = m, and n and m each independently represent an integer of 7 to 14 in the case of n ≠ m; X - represents a nitrate ion or a chlorate ion.

2. The latent heat storage material according to claim 1, wherein The phase transition temperature is 60°C or lower.

3. The latent heat storage material according to claim 1, which is used for an electronic device or a power storage device.

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

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

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

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