WO2022071182A1 - 蓄熱材、蓄熱材組成物、及び、蓄熱成形体 - Google Patents

蓄熱材、蓄熱材組成物、及び、蓄熱成形体 Download PDF

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WO2022071182A1
WO2022071182A1 PCT/JP2021/035260 JP2021035260W WO2022071182A1 WO 2022071182 A1 WO2022071182 A1 WO 2022071182A1 JP 2021035260 W JP2021035260 W JP 2021035260W WO 2022071182 A1 WO2022071182 A1 WO 2022071182A1
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Prior art keywords
heat storage
storage material
component
less
acid
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PCT/JP2021/035260
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English (en)
French (fr)
Japanese (ja)
Inventor
良太郎 天野
茂人 上村
成大 上田
直登 大槻
和裕 小田
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NOF Corp
SK Kaken Co Ltd
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NOF Corp
SK Kaken Co Ltd
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Priority to KR1020237010878A priority Critical patent/KR20230075458A/ko
Priority to CN202180066540.8A priority patent/CN116457439B/zh
Priority to JP2022553931A priority patent/JP7853215B2/ja
Publication of WO2022071182A1 publication Critical patent/WO2022071182A1/ja
Anticipated expiration legal-status Critical
Priority to JP2025277687A priority patent/JP2026040599A/ja
Ceased legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K5/00—Heat-transfer, heat-exchange or heat-storage materials, e.g. refrigerants; Materials for the production of heat or cold by chemical reactions other than by combustion
    • C09K5/02—Materials undergoing a change of physical state when used
    • C09K5/06—Materials undergoing a change of physical state when used the change of state being from liquid to solid or vice versa
    • C09K5/063—Materials absorbing or liberating heat during crystallisation; Heat storage materials
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K5/00—Heat-transfer, heat-exchange or heat-storage materials, e.g. refrigerants; Materials for the production of heat or cold by chemical reactions other than by combustion
    • C09K5/02—Materials undergoing a change of physical state when used
    • C09K5/06—Materials undergoing a change of physical state when used the change of state being from liquid to solid or vice versa
    • F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
    • F28—HEAT EXCHANGE IN GENERAL
    • F28D—HEAT-EXCHANGE APPARATUS, NOT PROVIDED FOR IN ANOTHER SUBCLASS, IN WHICH THE HEAT-EXCHANGE MEDIA DO NOT COME INTO DIRECT CONTACT
    • F28D20/00—Heat storage plants or apparatus in general; Regenerative heat-exchange apparatus not covered by groups F28D17/00 or F28D19/00
    • F28D20/02—Heat storage plants or apparatus in general; Regenerative heat-exchange apparatus not covered by groups F28D17/00 or F28D19/00 using latent heat
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E60/00—Enabling technologies; Technologies with a potential or indirect contribution to GHG emissions mitigation
    • Y02E60/14—Thermal energy storage

Definitions

  • the present invention relates to a heat storage material having excellent heat storage properties, a heat storage material composition, and a heat storage molded body obtained from the heat storage material composition.
  • an organic latent heat storage material that stores heat (heat storage) when a substance changes phase from solid to liquid and releases heat (heat dissipation) when the phase changes from liquid to solid. Has a high latent heat and is easy to handle, so research is being conducted for practical use.
  • Patent Document 1 discloses a heat storage body using an organic latent heat storage material such as methyl stearate or methyl partimate
  • Patent Document 2 discloses a total carbon number of 23.
  • a heat storage microcapsule using the following fatty acid ester and a fatty acid ester having a total carbon number of 20 or more as an organic latent heat storage material is disclosed.
  • the latent heat storage material is expected to be used as a building material for houses and transportation materials for foods and chemicals, but in actual use, it may be exposed to high temperature environments or come into contact with water. In such a case, there is a possibility that problems such as deterioration of radiation resistance and deterioration of heat storage performance due to hydrolysis may occur, and further improvement in performance has been desired.
  • the problem to be solved by the present invention is the heat storage property, in particular, the melting point and the freezing point can be approximated, and a desired set temperature can be obtained regardless of the temperature change from high temperature to low temperature or low temperature to high temperature.
  • It contains a heat storage material that can contribute to exhibiting excellent heat storage, radiation resistance, and hydrolysis resistance, and the heat storage material, and even when the heat storage material content is high, it has excellent curability and molding.
  • a heat storage material composition that can obtain a heat storage molded body with high latent heat per unit volume and excellent heat storage performance. Even when exposed to a high temperature environment, the heat storage material does not easily dissipate or leak from the inside, and is resistant to heat.
  • An object of the present invention is to provide a heat storage molded body having excellent dissipation and leakage resistance.
  • the present invention uses a heat storage material (organic latent heat storage material) containing a saturated fatty acid monoester having a specific structure, thereby providing excellent heat storage, radiation resistance, and heat storage resistance. It contains a heat storage material that can contribute to exhibiting hydrolysis resistance, and even when the heat storage material content is high, it has excellent curability, a high latent heat amount per unit volume of the molded body, and heat storage property.
  • a heat storage material composition that can obtain an excellent heat storage molded body, even when exposed to a high temperature environment, the heat storage material does not easily dissipate or leak from the inside, and a heat storage molded body with excellent radiation resistance and leakage resistance is obtained. It was found that the present invention could be completed.
  • the present invention is a saturated aliphatic monocarboxylic acid having a linear alkyl group having 8 or more and 20 or less carbon atoms, and a saturated fatty acid group having a linear alkyl group having 8 or more and 20 carbon atoms or less.
  • the present invention relates to a heat storage material comprising a saturated fatty acid monoester (A) obtained by reacting with a monoalkane.
  • the saturated fatty acid monoester (A) is a saturated aliphatic monocarboxylic acid (ac) having a linear alkyl group having 8 or more and 20 or less carbon atoms (Nc), and a saturated fatty acid monocarboxylic acid (ac). It is obtained by reacting with a saturated aliphatic monoalcohol (aa) having a linear alkyl group having 8 or more and 20 or less carbon atoms (Na). It is preferable to contain a saturated fatty acid monoester (A-1) satisfying the following formula (1). (1) (Nc) ⁇ (Na)
  • the saturated fatty acid monoester (A-1) satisfies the following formula (2). (2) 22 ⁇ (Nc + Na) ⁇ 32
  • the saturated fatty acid monoester (A-1) satisfies the following formula (3).
  • the present invention relates to a heat storage material composition containing the heat storage material, the polyol (B), and the isocyanate (C).
  • the polyol (B) contains a polyester polyol (B-1) and a polyether polyol (B-2).
  • the content ratio of the heat storage material in the total amount of the heat storage material composition is preferably 50% by mass or more and 95% by mass or less.
  • the heat storage material composition of the present invention preferably contains a polyester polyol having a number average molecular weight of 1000 or more and 4000 or less and a functional group number of 2 or more and less than 3 as the component (B-1).
  • the heat storage material composition of the present invention preferably contains a polyether polyol having a number average molecular weight of 1000 or more and 12000 or less and a functional group number of 2 or more and 3 or less.
  • the component (C) contains a trimer of isocyanate.
  • the total amount of the (B-1) component and the (B-2) component and the mixing ratio of the (C) component are 0.75 or more in terms of NCO / OH ratio. It is preferably 2.2 or less.
  • the present invention relates to a heat storage molded body characterized by being formed from the heat storage material composition.
  • the heat storage material of the present invention has excellent heat storage properties, in particular, it can approximate the melting point and the freezing point, and is excellent at a desired set temperature for any temperature change from high temperature to low temperature or low temperature to high temperature. It is useful because it can contribute to the exertion of heat storage resistance, radiation resistance, and hydrolysis resistance.
  • the heat storage molded product obtained by using the heat storage material composition containing the heat storage material has excellent curability even when the heat storage material content ratio is high, and the latent heat amount per unit volume of the molded body is high. High and excellent in heat storage. Further, even when the heat storage molded product is exposed to a high temperature environment, the heat storage material does not easily dissipate or leak from the inside, and is excellent in dissipation resistance and leakage resistance, which is very useful.
  • the present invention comprises a saturated aliphatic monocarboxylic acid having a linear alkyl group having 8 or more and 20 or less carbon atoms, and a saturated monocarboxylic acid having a linear alkyl group having 8 or more and 20 carbon atoms or less.
  • the present invention relates to a heat storage material comprising a saturated fatty acid monoester (A) (component (A)) obtained by reacting with an aliphatic monoalkane.
  • the component (A) functions as a heat storage material, has excellent heat storage properties, is difficult to dissipate even when exposed to a high temperature environment, has excellent dissipation resistance, and exhibits hydrolysis resistance.
  • the heat storage molded body formed from the heat storage material composition can contribute, and can exhibit excellent heat storage property at a desired set temperature against any temperature change from high temperature to low temperature or low temperature to high temperature. Further, it is hard to leak from the heat storage molded body formed from the heat storage material composition and has excellent leakage resistance.
  • Component (A-1) The component (A) is a saturated aliphatic monocarboxylic acid (ac) having a linear alkyl group having 8 or more and 20 or less carbon atoms (Nc), and a carbon number (Na). ) Is obtained by reacting with a saturated aliphatic monoalcohol (aa) having 8 or more and 20 or less linear alkyl groups, and the saturated fatty acid monoester (A-1) satisfying the following formula (1). (Component (A-1)) is preferably contained. By satisfying the following formula (1), the component (A-1) has excellent heat storage and dissipation resistance, more excellent hydrolysis resistance, and further, from high temperature to low temperature, or from low temperature to high temperature.
  • the heat storage material of the present invention contains a component (ac) having a specific structure and a component (A-1) having a specific range of carbon atoms obtained by reacting the component (a) having a specific structure.
  • a component (ac) having a specific structure a component having a specific range of carbon atoms obtained by reacting the component (a) having a specific structure.
  • the melting point and the freezing point of the component (A-1) can be approximated, and excellent heat storage property is obtained at a desired set temperature with respect to any temperature change from high temperature to low temperature or low temperature to high temperature. Can be demonstrated and becomes useful.
  • the component (A-1) can be adjusted to a desired temperature by the combination of the component (ac) having a specific structure and the component (aa), for example, pinpoint. It is useful because it can exhibit excellent heat storage property at the desired temperature.
  • the component (A-1) is hard to dissipate even when exposed to a high temperature environment and has excellent dissipation resistance, and also has excellent hydrolysis resistance even in the presence of water.
  • the “desired temperature” is not particularly limited and can be adjusted, but it can be set to, for example, a temperature range of 10 ° C to 40 ° C or a temperature range including a lower temperature below freezing point. ..
  • the difference between the melting point and the freezing point of the component (A-1) is preferably less than 2.5 ° C, more preferably less than 2.0 ° C, and further preferably less than 1.0 ° C.
  • the difference is less than 2.5 ° C., it has excellent heat storage property at a desired set temperature with respect to any temperature change from high temperature to low temperature or low temperature to high temperature, which is preferable.
  • the component (A-1) satisfies the above formula (1) and the following formula (2).
  • the component (A-1) is excellent in heat storage and dissipation resistance when the total number of carbon atoms (Nc + Na) is within the above range by satisfying the following formula (2), and further. It exhibits excellent heat storage resistance at a desired set temperature against any temperature change from high temperature to low temperature and low temperature to high temperature, and also exhibits excellent heat storage property, which will be described later (B-1) component.
  • B-2) Excellent compatibility with the component, excellent formability and curability when forming a heat storage molded body, easy to be supported and held inside the heat storage molded body, and more emission resistance and leakage resistance. It is preferable because it has excellent properties and prevents migration of heat storage material.
  • the melting point, freezing point, phase change temperature, and latent heat of the saturated fatty acid monoester such as the component (A-1) can be measured by a differential scanning calorimeter (DSC7000X manufactured by Hitachi High-Tech Science Co., Ltd.). ..
  • the measurement conditions are a melting point (° C), a freezing point (° C), a latent heat of solidification (J / g), and a latent heat of melting at a temperature rise / fall speed of 10 ° C / min in a temperature range of -40 ° C to 60 ° C.
  • the amount (J / g) was measured.
  • the phase change temperature is the average value of the freezing point (° C) and the melting point (° C)
  • the latent heat amount is the average value of the solidification latent heat amount (J / g) and the melting latent heat amount (J / g). ..
  • the component (A-1) satisfies the above formula (1) and the following formula (3).
  • the component (A-1) can exhibit better heat storage at a desired set temperature by making the melting point and the freezing point closer to each other. It is useful because it can improve hydrolysis resistance.
  • the component (A-1) has the carbon number (Nc) of 8 or more and 16 or less and the carbon number (Na) of 12 or more and 20 or less, and the following formula.
  • Nc carbon number
  • the conditions of the following formula more excellent heat storage can be exhibited at a desired set temperature.
  • the melting point can be further increased. It is useful because the freezing point can be approximated and the hydrolysis resistance can be improved.
  • the content of the component (A-1) is preferably more than 10% by mass, more preferably more than 30% by mass, based on 100% by mass of the total amount of the heat storage material. , It is more preferably contained in an amount of more than 50% by mass, and particularly preferably it is contained in an amount of more than 70% by mass.
  • the upper limit is preferably 100% by mass.
  • the saturated fatty acid monoester (A) is a saturated fatty acid monocarboxylic acid (a) having a linear alkyl group having 8 or more and 20 or less carbon atoms (Nc).
  • -C) and a saturated aliphatic monoalcohol (aa) having a linear alkyl group having 8 or more and 20 or less carbon atoms (Na) are reacted and satisfy the following formula (4).
  • the component (A-2) is preferable because it is excellent in heat storage and radiation resistance by satisfying the following formula (4). Further, by further satisfying the following formula (4') as the component (A-2), the above effect can be further exhibited, which is a more preferable embodiment.
  • the component (A-2) satisfies the above formula (4) and the following formula (2).
  • the component (A-2) is preferable because it satisfies the following formula (2) and is excellent in heat storage property and dissipation resistance.
  • the heat storage material composition of the present invention only one type of component (A) may be used as the heat storage material, or two or more types may be mixed and used.
  • the temperature setting in the temperature range, which was difficult with only one kind of the component (A) can be easily adjusted, which is useful.
  • two or more kinds of the (A-1) component may be used in combination with respect to only one kind of the (A-1) component, or the above (A-1) component may be used in combination with the above (A-1) component.
  • -2) It is preferable to mix and use the components, which facilitates the desired temperature setting, the difference between the melting point and the freezing point can be adjusted, and exhibits excellent heat storage at the desired set temperature. be able to.
  • the mixing ratio (molar ratio) of the component (A-1) and the component (A-2) is the same.
  • the component (A-2) preferably further satisfies at least one selected from the following formula (2'), more preferably two or more.
  • the component (A-2) preferably further satisfies at least one selected from the following formula (2'), more preferably two or more.
  • the component (ac) is a saturated aliphatic monocarboxylic acid having a linear alkyl group having 8 or more and 20 or less carbon atoms, preferably having a carbon number (Nc) of 8 or more and 20 or less. It is a saturated aliphatic monocarboxylic acid having a linear alkyl group of 8 or more and 16 or less, and more preferably a saturated aliphatic monocarboxylic acid having a linear alkyl group having 10 or more and 14 or less carbon atoms (Nc). ..
  • Examples of the component (ac) include n-octanoic acid, n-nonanoic acid, n-decanoic acid, n-undecanoic acid, n-dodecanoic acid, n-tridecanoic acid, n-tetradecanoic acid, and n-pentadecane. Acids, n-hexadecanoic acid, n-heptadecanoic acid, n-octadecanoic acid, n-nonadecanoic acid, n-icosanoic acid and the like can be mentioned, and one or more of these can be used.
  • the component (aa) is a saturated aliphatic monoalcohol having a linear alkyl group having 8 or more and 20 or less carbon atoms, preferably 10 carbon atoms (Na). It is a saturated aliphatic monoalcohol having a linear alkyl group of 20 or more, and more preferably a saturated aliphatic monoalcohol having a linear alkyl group having 10 or more and 18 or less carbon atoms.
  • Examples of the component (a) include 1-octanol, 1-nonanol, 1-decanol, 1-undecanol, 1-dodecanol, 1-tridecanol, 1-tetradecanol, 1-pentadecanol, 1-. Hexadecanol, 1-heptadecanol, 1-octadecanol, 1-nonadecanol, 1-icosanol and the like can be mentioned, and one or more of these can be used.
  • the total number of carbon atoms (Nc) of the linear alkyl group of the component (ac) and the carbon number (Na) of the linear alkyl group of the component (a) is 20 or more and 32 or less. It is preferably 22 or more and 32 or less, and more preferably 24 or more and 32 or less.
  • the heat storage property and the dissipation resistance are excellent, and the compatibility with the components (B-1) and (B-2) described later is obtained. It is excellent, has excellent formability and curability when forming a heat storage molded body, is easily supported and held inside the molded body, and is more excellent in emission resistance and leakage resistance, which is preferable.
  • Examples of the component (A-1) include nonyl octanate, decyl octanate, undecyl octanoate, dodecyl octanoate, tridecyl octanoate, tetradecyl octanoate, pentadecyl octanoate, hexadecyl octanoate, heptadecyl octanoate, and octanoic acid.
  • Examples of the component (A-2) include, for example. Octyl octanate, Octyl nonanoate, nonyl nonanate, Octyl decanoate, nonyl decanoate, decyl decanoate, Octyl undecanoate, nonyl undecanoate, decyl undecanoate, undecyl undecanoate, Octyl dodecanoate, nonyl dodecanoate, decyl dodecanoate, undecylic dodecanoate, dodecyl dodecanoate, Octyl tridecanoate, nonyl tridecanoate, decyl tridecanoate, undecyl tridecanoate, dodecyl tridecanoate, tridecyl tridecane, Octyl tetradecanoate, nonyl tetradecanoate, decyltetradecanoate, undecylic acid tetradecanoate, dodec
  • the component (A) can be produced by a normal esterification reaction and a transesterification reaction.
  • esterification if necessary, distilling under reduced pressure, washing with water after alkali neutralization, activated clay and synthesis for the purpose of removing unreacted saturated aliphatic monocarboxylic acids and saturated aliphatic monoalcohols.
  • Known purification methods such as adsorption treatment using a system adsorbent and steaming can be performed.
  • the latent heat amount of the component (A) component is preferably 120 J / g or more, more preferably 150 J / g or more, and as an upper limit value, as a lower limit value. Is preferably 260 J / g or less, and more preferably 250 J / g or less.
  • the acid value of the component (A) is preferably 1 mgKOH / g or less, more preferably 0.5 mgKOH / g or less, still more preferably 0.1 mgKOH / g, from the viewpoint of hydrolysis resistance. It is less than or equal to g.
  • the hydroxyl value of the component (A) is preferably 2 mgKOH / g or less, more preferably 1 mgKOH / g or less, still more preferably 0.5 mgKOH / g or less, from the viewpoint of heat storage at a desired set temperature. Is.
  • heat storage materials may be mixed with the component (A) as long as the characteristics of the present invention are not impaired.
  • Examples of the other heat storage material include fatty acid esters, fatty acids, aliphatic hydrocarbons, and aliphatic alcohols other than the component (A).
  • Examples of the fatty acid ester other than the component (A) include a fatty acid ester composed of the component (ac) and an alcohol other than the component (a), a carboxylic acid other than the component (ac), and the above-mentioned (.
  • Examples thereof include a fatty acid ester composed of a) component, a fatty acid ester composed of a carboxylic acid other than the above-mentioned (ac) component, and an alcohol other than the (a) component.
  • Examples of the carboxylic acid other than the component (ac) include a monocarboxylic acid having a linear alkyl group having 1 to 7 carbon atoms and a monocarboxylic acid having a linear alkyl group having 21 to 30 carbon atoms. , Monocarboxylic acid having a branched alkyl group having 3 to 30 carbon atoms, polyvalent carboxylic acid having an alkyl group having 2 to 30 carbon atoms, unsaturated carboxylic acid having an alkyl group having 4 to 30 carbon atoms, etc. Can be mentioned.
  • alcohols other than the component (a) include, for example, a monoalcohol having a linear alkyl group having 1 or more and 7 or less carbon atoms, a monoalcohol having a linear alkyl group having 21 or more and 30 or less carbon atoms, and a carbon number of carbon atoms.
  • examples thereof include monoalcohols having 3 or more and 30 or less branched alkyl groups, polyhydric alcohols having 2 or more and 30 or less carbon atoms, and unsaturated alcohols having 4 or more and 30 or less carbon atoms.
  • the content ratio of the component (A) is preferably 50% by mass or more and 90% by mass or less, and 60% by mass or more and 85% by mass or less, based on the total amount of the heat storage material composition. It is more preferably 70% by mass or more and 80% by mass or less, and particularly preferably 70% by mass or more and 78% by mass or less.
  • the content ratio of the component (A) is within the above range, the component (A) is supported and retained even when a heat storage material composition containing a very large amount of the component (A) is used. It has excellent properties, is excellent in formability and curability when forming a heat storage molded body, and can prevent leakage of the component (A) (leakage resistance), and the obtained heat storage molded body has excellent heat storage properties. Can be useful.
  • the present invention relates to a heat storage material composition containing the heat storage material containing the component (A), the polyol (B), and the isocyanate (C).
  • the heat storage material composition forms a three-dimensional network structure by the reaction of the polyol (B) and the isocyanate (C), and the heat storage material containing the component (A) enters the network structure to form a heat storage molded body. Even when the heat storage material containing the component (A) is supported and held and exposed to a high temperature environment, the heat storage material containing the component (A) is released and leaked. It is difficult, has excellent radiation resistance and leakage resistance, and is preferable.
  • polyol (B) Component Examples of the polyol (B) include polyester polyol, polyether polyol, acrylic polyol, polycarbonate polyol, polyolefin polyol, polycaprolactone polyol, polytetramethylene glycol polyol, polybutadiene polyol, polyoxypropylene polyol, and polyoxy. Examples thereof include propylene ethylene polyols, epoxy polyols, alkyd polyols, fluorine-containing polyols, silicon-containing polyols, celluloses and / or derivatives thereof, polysaccharides such as amylose, and one or more of these can be used.
  • the polyol (B) contains a polyester polyol (B-1) and / or a polyether polyol (B-2).
  • a polyol (B) is preferable because it has excellent curability and makes it easy to uniformly support and hold the heat storage material in the three-dimensional network structure.
  • the polyol (B) preferably contains a polyester polyol (B-1) (component (B-1)).
  • the component (B-1) is a component that reacts with isocyanate (C) described later to form a three-dimensional network structure.
  • the support and retention of the heat storage material containing the component (A) is excellent, and the emission resistance and leakage resistance of the heat storage material containing the component (A) are enhanced. be able to.
  • Examples of the component (B-1) include a condensed polymer of a polyhydric alcohol and a polyvalent carboxylic acid; a condensed polymer of a polyhydric alcohol and a hydroxycarboxylic acid; a ring-opened polymer of a cyclic ester (lactone); Reactants of three or more components of polyhydric alcohols, polyvalent carboxylic acids, hydroxycarboxylic acids and cyclic esters; examples include castor oil or modified products thereof.
  • polyvalent alcohol examples include ethylene glycol, diethylene glycol, propylene glycol, dipropylene glycol, trimethylene glycol, 1,2-butanediol, 1,3-butanediol, 1,4-butanediol, and 2,3-.
  • polyvalent carboxylic acid examples include malonic acid, maleic acid, maleic anhydride, succinic acid, glutaric acid, adipic acid, suberic acid, azelaic acid, sebacic acid, dodecanedioic acid, tridecanedioic acid, and tetradecanedioic acid.
  • Aliphatic dicarboxylic acids such as pentadecanedioic acid, hexadecanedioic acid, octadecanedioic acid, and nonadecandioic acid, alicyclic dicarboxylic acids such as 1,4-cyclohexanedicarboxylic acid, terephthalic acid, isophthalic acid, orthophthalic acid, phthalic anhydride, Aromatic dicarboxylic acids such as terephthalic acid, 2,6-naphthalenedicarboxylic acid, paraphenylenedicarboxylic acid and trimellitic acid, Palmitoreic acid, oleic acid, linoleic acid, linolenic acid, eicosenoic acid, palm oil fatty acid, palm oil fatty acid, soybean oil fatty acid, hydrogenated soybean oil fatty acid, flaxseed oil fatty acid, safflower fatty acid, tung oil fatty acid, tall oil fatty
  • hydroxycarboxylic acid examples include 2-hydroxybutanoic acid, 2-hydroxypentanoic acid, 3-hydroxypentanoic acid, 3-hydroxyhexanoic acid, 2-hydroxyheptanoic acid, 3-hydroxyheptanoic acid and 2-hydroxyoctanoic acid.
  • 3-Hydroxyoctanoic acid 4-Hydroxynonanoic acid, 3-Hydroxydecanoic acid, 3-Hydroxydodecanic acid, 5-Hydroxydodecanic acid, 3-Hydroxytridecanoic acid, 6-Hydroxytetradecanoic acid, 2-Hydroxypentadecanoic acid, 10-Hydroxyhexadecanoic acid, 11-hydroxyheptadecanoic acid, 10-hydroxyoctadecanoic acid, 12-hydroxyoctadecanoic acid, 10-hydroxynonadecanoic acid, 2-hydroxyicosanoic acid, 2-hydroxytetradocosanoic acid, ricinoleic acid, Lycine lysinic acid, Celebronic acid, Leucic acid, Salicylic acid, Glyceric acid, 3-Hydroxypropionic acid, 5-Hydroxypentanoic acid, 6-
  • examples of the cyclic ester include propiolactone, ⁇ -methyl- ⁇ -valerolactone, ⁇ -caprolactone and the like.
  • the method for producing the polyester polyol can be carried out by a conventional method, and if necessary, a known curing agent, curing catalyst or the like may be used.
  • a component constituting the polyester polyol one selected from polyhydric alcohols, polyvalent carboxylic acids, and hydroxycarboxylic acids having an alkyl segment having 14 or more and 22 or less carbon atoms and 16 or more and 20 or less carbon atoms. It is preferable to include the above. Further, it is preferable to use a divalent or trivalent alcohol as the polyhydric alcohol. Further, it is preferable to use a divalent or trivalent carboxylic acid as the polyvalent carboxylic acid.
  • the number average molecular weight (Mn) of the component (B-1) is preferably 1000 or more and 4000 or less, more preferably 1500 or more and 3500 or less, and further preferably 1800 or more and 3500 or less.
  • Mn number average molecular weight
  • the number of functional groups of the component (B-1) is preferably 2 or more and less than 3, and more preferably 2 or more and 2.5 or less. When the number of functional groups of the component (B-1) is within the above range, the curability is excellent, and it becomes easy to uniformly support and hold the heat storage material containing the component (A) in the three-dimensional network structure. preferable.
  • the number of functional groups of the component (B-1) is an average value of the number of hydroxyl groups per molecule.
  • the polyol (B) preferably contains a polyether polyol (B-2) (component (B-2)).
  • the component (B-2) is a component that reacts with isocyanate (C) described later to form a three-dimensional network structure.
  • the component (B-2) has excellent curability and forms a stronger three-dimensional network structure, and it is easy to uniformly support and hold the heat storage material containing the component (A) in the three-dimensional network structure. Therefore, the heat storage material containing the component (A) can be uniformly supported and held even with a high content.
  • component (B-2) examples include polyalkylene glycols such as polyethylene glycol, polypropylene glycol, polytetramethylene glycol, polyethylene glycol monoalkyl ether, and polypropylene glycol monoalkyl ether, as well as ethylene oxide-propylene oxide copolymers.
  • Bisphenol A type polyether polyol obtained by adding.
  • Aromatic amines eg, toluenediamine, diethyltoluenediamine, 4,4'-diaminodiphenylmethane, p-phenylenediamine, o-phenylenediamine, naphthalenediamine, Aromatic amine-based polyether polyol obtained by adding alkylene oxide using triethanolamine, Mannig condensate, etc.
  • polyether polyol obtained by adding alkylene oxide using glycerin as an initiator, low molecular weight
  • examples thereof include an amino group-containing polyether polyol having an amine (for example, ethylenediamine, propylenediamine, butylene diamine, hexamethylenediamine, neopentyldiamine, etc.) as an initiator and an alkylene oxide added.
  • an amine for example, ethylenediamine, propylenediamine, butylene diamine, hexamethylenediamine, neopentyldiamine, etc.
  • the number average molecular weight (Mn) of the component (B-2) is preferably 1000 or more and 12000 or less, more preferably 1000 or more and 10000 or less, further preferably 2000 or more and 8000 or less, and 3000 or more. 7000 or less is particularly preferable. When the number average molecular weight of the component (B-2) is within the above range, the curability is more excellent, which is preferable.
  • the number of functional groups of the component (B-2) is preferably 2 or more and 3 or less, more preferably 2 or more and less than 3, and further preferably 2 or more and 2.5 or less. When the number of functional groups of the component (B-2) is within the above range, the curability is more excellent, which is preferable.
  • the number of functional groups of the component (B-2) is an average value of the number of hydroxyl groups per molecule.
  • the content ratio (mass ratio) of the (B-1) component and the (B-2) component is such that the (B-1) component: (B-2) component is 50:50 to 100: 0. It is preferably 50:50 to 99: 1, more preferably 55:45 to 95: 5, and particularly preferably 60:40 to 85:15.
  • the content ratio of the component (B-1) and the component (B-2) is within the above range, it is more excellent in formability and curability, which is preferable.
  • polyols other than the component (B-1) and the component (B-2) can be used as long as the characteristics of the present invention are not impaired.
  • examples of the polyols other than the component (B-1) and the component (B-2) include acrylic polyols, polycarbonate polyols, polyolefin polyols, polycaprolactone polyols, polytetramethylene glycol polyols, polybutadiene polyols, and polyoxypropylene polyols.
  • Examples thereof include polyoxypropylene ethylene polyols, epoxy polyols, alkyd polyols, fluorine-containing polyols, silicon-containing polyols, celluloses and / or derivatives thereof, polysaccharides such as amylose, and the like.
  • the polyolefin polyol is a polyol having an olefin as a component of the skeleton (or main chain) of a polymer or a copolymer and having at least two hydroxyl groups in the molecule (particularly at the terminal), and has a number average molecular weight (number average molecular weight). Those having Mn) of 1500 or more can be used.
  • the olefin may be an olefin having a carbon-carbon double bond at the terminal (for example, ⁇ -olefin such as ethylene or propylene), or an olefin having a carbon-carbon double bond at a site other than the terminal. It may be (eg, isobutene, etc.) or even a diene (eg, butadiene, isoprene, etc.).
  • the heat storage material composition of the present invention preferably contains the isocyanate (C) ((C) component)). Since the component (C) forms a three-dimensional network structure together with the component (B) described above, the heat storage molded body is formed in a state where the heat storage material containing the component (A) enters the network structure. Even when the heat storage material containing the component (A) is supported and held and exposed to a high temperature environment, the heat storage material containing the component (A) is less likely to be released and leaked, and is resistant to leakage. It has excellent radiation resistance and leakage resistance, and is useful.
  • the component (C) is isocyanate, and is not limited as long as it has an isocyanate group, but preferably has two or more isocyanate groups in one molecule, and more preferably 2.2 or more.
  • the isocyanate include 1,3-trimethylethylene diisocyanate, 1,4-tetramethylene diisocyanate, 1,3-pentamethylene diisocyanate, 1,5-pentamethylene diisocyanate, and 1,6-hexamethylene diisocyanate (HMDI).
  • the component (C) contains a trimer obtained by trimerizing (isocyanurate) isocyanate.
  • trimerizing isocyanurate
  • the trimer it becomes easier to form a three-dimensional network structure together with the component (B), and the effect of the present invention can be further enhanced.
  • the heat storage material composition of the present invention contains the heat storage material containing the component (A), the component (B), and the component (C), and the component (B) and the component (C).
  • the components can be reaction-cured to obtain a heat storage molded product.
  • the heat storage material composition of the present invention first, the heat storage material containing the component (A) and the component (B) are mixed, and then the component (C) is mixed and reaction-cured to store heat. It is preferable to obtain a molded product.
  • the mixing ratio of the component (B) and the component (C) is preferably 0.75 or more and 2.2 or less in terms of NCO / OH ratio (equivalent ratio). It is more preferably 0.9 to 2.1, and further preferably 1.05 or more and 2.0 or less.
  • NCO / OH ratio is within the above range, it is excellent in formability and curability, forms a stronger three-dimensional network structure, and stores heat containing the component (A) in the three-dimensional network structure. It becomes easy to support and hold the material uniformly, which is useful.
  • the heat storage material composition of the present invention is, for example, a layered clay mineral, a surfactant, a heat conductive substance, a compatibilizer, a reaction accelerator, a flame retardant, a pigment, a bone, in addition to the heat storage material containing the component (A).
  • viscosity regulators plasticizers, buffers, dispersants, cross-linking agents, pH regulators, preservatives, fungicides, antibacterial agents, algae-proofing agents, wetting agents, defoaming agents, leveling agents, lubricants, dehydrating agents It can also contain additives such as UV absorbers, antioxidants, light stabilizers, fibers, fragrances, chemical substance adsorbents, photocatalysts, moisture-absorbing and desorbing powders and granules.
  • additives such as UV absorbers, antioxidants, light stabilizers, fibers, fragrances, chemical substance adsorbents, photocatalysts, moisture-absorbing and desorbing powders and granules.
  • the present invention relates to a heat storage molded body characterized by being formed from the heat storage material composition.
  • the heat storage molded body can be obtained by curing the heat storage material composition, or can be applied by laminating the heat storage molded body and various base materials, and the heat storage material composition is permeated into the porous base material. It can be impregnated and cured and applied as a heat storage member, or the heat storage member and various base materials can be laminated and applied.
  • the latent heat amount of the heat storage molded product is preferably 70 J / g or more, more preferably 100 J / g or more, and the upper limit value is preferably 220 J / g. It is / g or less, more preferably 200 J / g or less.
  • the phase change temperature (melting point or freezing point) of the heat storage molded product is preferably about 10 to 60 ° C, more preferably about 15 to 50 ° C, for example, when used for interior / exterior materials such as buildings.
  • porous substrate examples include natural fibers such as cotton, linen, wool and silk, organic fibers such as nylon, tetron, acrylic, polyester, polyurethane, vinylon, rayon, aramid and azole, and inorganic fibers such as glass.
  • porous base material such as bamboo charcoal, a wood base material such as charcoal, and a foamed resin base material such as a foamed urethane board and a foamed styrene board.
  • Examples of the various base materials include heat insulating base materials such as polystyrene foam, polyurethane foam, acrylic resin foam, phenol resin foam, polyethylene resin foam, foamed rubber, glass wool, rock wool, and foamed ceramic.
  • Examples include resin base materials such as acrylic resin and vinyl resin, glass base materials, metal base materials such as copper, aluminum, iron, brass, zinc, magnesium and nickel, inorganic base materials such as concrete, and the porous base materials. Be done.
  • the heat storage material of the present invention, the heat storage material composition containing the heat storage material, and the heat storage molded body obtained by using the heat storage material are mainly the inner wall material, the outer wall material, the ceiling material, the floor material of a building such as a house, and the heat storage molded body thereof. It can be suitably used as a material for interior / exterior materials such as a bonding material and a partition material.
  • the heat storage material composition of the present invention is, for example, a floor heating system, a cooling / heating system, an interior material such as a vehicle, an industrial product such as a machine / equipment, a thermoelectric conversion system, a heat insulating material, a frigid region or a fire region, or a polar region.
  • the heat storage material and the heat storage material composition of the present invention can be used by various methods, for example, a method of encapsulating in a case, a bag or the like, impregnating with a base material, or encapsulating is adopted. It is also useful because it can be fixed together with the binder.
  • the acid value of the reaction solution is measured every hour, and the decrease in acid value per hour is 0.5 mgKOH / g or less.
  • the reaction was carried out until it became.
  • the reaction was then reduced to 30 Torr at 220 ° C. to remove alcohol and volatile reaction by-products.
  • the mixture was stirred for 1 hour. After stopping the stirring, the mixture was allowed to stand for 30 minutes to remove the aqueous layer separated into the lower layer.
  • thermocouple (Melting point and freezing point measurement test) Prepare two sheets of 22 g of each fatty acid ester (heated at 50 ° C.) shown in Tables 1 and 2 soaked in a wood board (130 mm x 85 mm x 6 mm), and thermocouple the center of the two wood boards. A pair was sandwiched and a test piece was obtained. The obtained test piece was allowed to stand in a thermocouple at 39 ° C. for 6 hours, then moved to a thermocouple at 19 ° C. and allowed to stand for 3 hours, and then allowed to stand in a thermocouple at 39 ° C. for 3 hours. The temperature change at the time of making was measured by a thermocouple, and the measurement result (Example 1 shown below) is shown in FIG.
  • the melting point (° C.) and the freezing point (° C.) were measured by the tangential method shown in FIG. 1, and the difference between the melting point and the freezing point (° C.) was calculated.
  • the evaluation is as follows. The evaluation results are shown in Table 3. The temperature in the incubator was set to + 10 ° C. and ⁇ 10 ° C. as a reference from the phase change temperature of the fatty acid ester to be measured. If the evaluation was 4, 3 or 2, it was judged to be valid. Further, as in Example 1, other Examples, Comparative Examples, and Reference Examples were also evaluated by preparing test specimens (other than Example 1 are not shown). 4: The difference between the melting point and the freezing point was less than 1 ° C.
  • the difference between the melting point and the freezing point was 1 ° C. or higher and lower than 2 ° C.
  • 2 The difference between the melting point and the freezing point was 2 ° C or more and less than 2.5 ° C.
  • 1 The difference between the melting point and the freezing point was 2.5 ° C. or more.
  • Heat storage test 1 Using each fatty acid ester shown in Tables 1 and 2, weigh 50 g on a metal container (160 mm ⁇ 109 mm ⁇ 27 mm), and use a differential scanning calorimeter (DSC7000X manufactured by Hitachi High-Tech Science) to determine the latent heat (J / g).
  • DSC7000X differential scanning calorimeter manufactured by Hitachi High-Tech Science
  • the average value was defined as the latent heat amount (J / g), and the heat storage property was evaluated.
  • the evaluation is as follows. The evaluation results are shown in Table 3 below. If the evaluation was 3 or 2, it was judged to be valid. 3: The latent heat amount was 150 J / g or more. 2: The latent heat amount was 120 J / g or more and less than 150 J / g. 1: The latent heat amount was less than 120 J / g.
  • the test piece obtained in the above curability test was cured in an atmosphere of 15 ° C. for 12 hours and then cured at 50 ° C. for 5 hours to obtain a test piece.
  • the obtained test piece was tilted by 45 °, and the amount of heat storage material leaked (leaked off) from the surface of the test piece was measured and evaluated.
  • the evaluation is as follows. The evaluation results are shown in Tables 5 and 6. When the evaluation was 5, 4, or 3, it was judged to be valid. 5: No leakage of the heat storage material was observed. 4: The amount of heat storage material leaked was less than 1%. 3: The amount of heat storage material leaked was 1% or more and less than 2%. 2: The amount of heat storage material leaked was 2% or more and less than 3%. 1: The amount of heat storage material leaked was 3% or more.
  • the test piece obtained in the curability test was evaluated by measuring the mass change before and after storage at 80 ° C. for 30 days. The evaluation is as follows. The evaluation results are shown in Tables 5 and 6. If the evaluation was 4 or 3, it was judged to be valid. 4: The mass change was less than 1%. 3: The mass change was 1% or more and less than 5%. 2: The mass change was 5% or more and less than 10%. 1: The mass change was 10% or more.
  • the latent heat (J / g) of the test piece obtained in the curability test was measured and evaluated with a differential scanning calorimeter (DSC7000X manufactured by Hitachi High-Tech Science Co., Ltd.). Specifically, the latent heat amount (J / g) was defined as the average value of the latent heat of solidification and the latent heat of melting measured at a temperature rise rate of 10 ° C./min and a temperature decrease rate of 10 ° C./min, and the heat storage property was evaluated. The evaluation is as follows. The evaluation results are shown in Tables 5 and 6. If the evaluation was 3 or 2, it was judged to be valid. 3: The latent heat amount was 100 J / g or more. 2: The latent heat amount was 70 J / g or more and less than 100 J / g. 1: The latent heat amount was less than 70 J / g.
  • test could not be performed because the test piece did not cure in the case of the leakage resistance test, and the radiation resistance test and the heat storage test. In the case of, it means that the test could not be performed accurately because it did not cure as a test piece or because there was a lot of leakage in the leakage resistance test.
  • the heat storage molded product obtained by using the heat storage material composition using the desired components (A) to (C) has curability. It was confirmed that it can contribute to heat storage, radiation resistance, and leakage resistance. On the other hand, in the comparative example and the reference example, none of the curability, heat storage property, radiation resistance, and leakage resistance could be obtained at the same time.

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