Sclerotic composition

Abstract

This application can provide a curable composition that exhibits a low density and is advantageous for weight reduction, has suppressed viscosity change over time, and has excellent storage stability and shelf stability, and its uses. Further, the curable composition exhibits excellent compatibility during the manufacturing process and, when cured, can form a cured product having high thermal conductivity, a low specific gravity (density), and relatively high hardness. This application can further provide an apparatus including the curable composition or its cured product.

Description

Technical Field

[0001] This application claims the benefit of priority based on Korean Patent Application No. 10-2022-0064080 filed on May 25, 2022, and all the contents disclosed in the literature of the Korean Patent Application are incorporated herein by reference in their entirety.

[0002] This application relates to a curable composition and its applications.

Background Art

[0003] With the development of ultra-high speed and ultra-small size technologies, devices and machines applied to such technologies are required to have higher power and faster speeds. Such high power and fast speeds cause more heat generation during the operation process, thereby increasing the demand for thermally conductive materials having a heat dissipation effect that can effectively disperse and / or remove heat.

[0004] For example, Patent Document 1 discloses a material in which a thermally conductive filler is blended with a polymer, and such a material is applied to a battery module.

[0005] As the polymer blended with the thermally conductive filler, polyurethane is used. A composition for forming such a material can be formed by reacting a main agent part containing a polyol compound and a curing agent part containing an isocyanate compound.

[0006] However, such a composition has problems such as the isocyanate group in the curing agent part showing high reactivity with moisture and the viscosity increasing over time. Therefore, it is necessary to ensure so-called storage stability and storage stability for such a composition.

[0007] In addition, in the composition as described above, a filler having thermal conductivity is relatively excessively compounded for heat dissipation performance. Usually, as such a filler, an oxide filler such as alumina is used. Such a filler is excellent in thermal conductivity, but has a high specific gravity, which hinders the weight reduction of the material.

[0008] For example, a hydroxide filler such as aluminum hydroxide has a low specific gravity and has thermal conductivity. However, although such a filler has thermal conductivity, its thermal conductivity characteristics are inferior to those of the oxide filler. In addition, the hydroxide filler has a hydroxyl group, and such a hydroxyl group can react with moisture or the isocyanate group of the curing agent. Therefore, when an excessive amount of the hydroxide filler is applied, it is difficult to ensure storage stability and storage stability, the compatibility is also reduced, and the thermal conductivity cannot be stably ensured.

[0009] In addition, since the hydroxide filler has a relatively low hardness, it is not suitable for forming a material that requires high hardness.

Prior Art Documents

Patent Documents

[0010]

Patent Document 1

Summary of the Invention

Problems to be Solved by the Invention

[0011] The present application provides a curable composition and its use. The present application can provide a curable composition that exhibits a low density, is advantageous for weight reduction, has excellent storage stability and storage stability with suppressed viscosity change over time, and its use. In addition, the curable composition exhibits excellent compatibility during the manufacturing process and, when cured, can form a cured product having high thermal conductivity, low specific gravity (density), and relatively high hardness. The present application further aims to provide an apparatus including the curable composition or its cured product.

Means for Solving the Problems

[0012] Among the physical properties mentioned in this application, unless otherwise specified, the physical properties whose measurement temperature affects the results are the physical properties measured at normal temperature.

[0013] Among the physical properties mentioned in this application, unless otherwise specified, the physical properties whose measurement pressure affects the results are the physical properties measured under normal pressure conditions.

[0014] Among the physical properties mentioned in this application, unless otherwise specified, the physical properties whose measurement humidity affects the results are the physical properties measured under normal humidity conditions.

[0015] In this specification, the term "normal temperature" means the natural temperature without heating or cooling. For example, the normal temperature may be any temperature within the range of 10°C to 30°C, and means a temperature of about 23°C or about 25°C. Unless otherwise specified, the unit of temperature mentioned in this specification is Celsius (°C).

[0016] In this specification, normal pressure means the natural pressure without pressurization or depressurization. For example, the normal pressure usually means about 1 atmosphere at the atmospheric pressure level.

[0017] In this specification, the term "normal humidity" means the natural humidity without special adjustment under the above normal temperature and normal pressure conditions. For example, the normal humidity means any humidity within the range of about 20RH% to 80RH% or about 40 to 60RH%. The unit RH% (Relative Humidity%) used above represents the current amount of water vapor as a percentage when the maximum amount of water vapor that can enter at a specific temperature is set to 100.

[0018] As used herein, the terms weight-average molecular weight (Mw) and number-average molecular weight (Mn) refer to the molecular weights measured using GPC (Gel permeation chromatography), and the unit thereof is g / mol. Further, the polydispersity index (PDI) of the terms used herein is the value (Mw / Mn) obtained by dividing the weight-average molecular weight (Mw) by the number-average molecular weight (Mn). The number-average molecular weight (Mn) and weight-average molecular weight (Mw) may be measured after putting a sample into a 20 mL vial, diluting it with THF (tetrahydrofuran) to a concentration of about 20 mg / mL, and then filtering the calibration standard sample and the sample to be analyzed through a syringe filter (pore size: 0.2 μm). As the analysis program, ChemStation of Agilent technologies may be used, and the number-average molecular weight (Mn) and weight-average molecular weight (Mw) can be determined by comparing the elution time of the sample with the calibration curve.

[0019] <GPC Measurement Conditions> Equipment: 1200 series of Agilent technologies Column: TL Mix.A&B of Agilent technologies is used Solvent: THF Column temperature: 40 °C Sample concentration: 20 mg / mL, 10 μl injection MP: 364000, 91450, 17970, 4910, 1300 are used as standard samples

[0020] As used herein, the term "curing" means a phenomenon in which the hardness or viscosity of a material increases through physical and / or chemical reactions.

[0021] As used herein, the term "curability" means the curable material.

[0022] As used herein, the term "substituent" means an atom or group of atoms that replaces a hydrogen atom present in any compound. Further, as will be described later, the substituents are not limited thereto, and unless otherwise specifically described in the present application, the substituents may be further substituted with the substituents described below or may not be substituted with any substituents.

[0023] As used herein, the term "alkyl group" refers to a straight-chain or branched-chain alkyl group or alkylene group having 1 to 20 carbon atoms, 1 to 16 carbon atoms, 1 to 12 carbon atoms, 1 to 8 carbon atoms, or 1 to 6 carbon atoms, or a cyclic alkyl group having 3 to 20 carbon atoms, 3 to 16 carbon atoms, 3 to 12 carbon atoms, 3 to 8 carbon atoms, or 3 to 6 carbon atoms, unless otherwise specified. Here, the cyclic alkyl group includes both an alkyl group having only a ring structure and an alkyl group containing a ring structure. For example, both the cyclohexyl group and the methylcyclohexyl group fall within the category of cyclic alkyl groups. Also, for example, specific alkyl groups include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethylpropyl, 1,1-dimethylpropyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, etc. Also, specific cycloalkyl groups or cycloalkylene groups include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, etc.

[0024] In this specification, unless otherwise specified, the alkenyl group or alkenylene group of the term refers to a linear or branched acyclic alkenyl group or alkenylene group having 2 to 20 carbon atoms, or 2 to 16 carbon atoms, or 2 to 12 carbon atoms, or 2 to 8 carbon atoms, or 2 to 6 carbon atoms, or a cyclic alkenyl group or alkenylene group having 3 to 20 carbon atoms, or 3 to 16 carbon atoms, or 3 to 12 carbon atoms, or 3 to 8 carbon atoms, or 3 to 6 carbon atoms. Here, when including an alkenyl group or alkenylene group with a ring structure, it corresponds to a cyclic alkenyl group or alkenylene group. Also, for example, ethenyl(ene), n-propenyl(ene), isopropenyl(ene), n-butenyl(ene), isobutenyl(ene), tert-butenyl(ene), sec-butenyl(ene), 1-methyl-butenyl(ene), 1-ethyl-butenyl(ene), n-pentenyl(ene), isopentenyl(ene), neopentyl(ene), tert-pentenyl(ene), n-hexenyl(ene), 1-methylpentenyl(ene), 2-methylpentenyl(ene), 4-methyl-2-pentenyl(ene), 3,3-dimethylbutenyl(ene), 2-ethylbutenyl(ene), n-heptenyl(ene), 1-methylhexenyl(ene), n-octenyl(ene), tert-octenyl(ene), 1-methylheptenyl(ene), 2-ethylhexenyl(ene), 2-propylpentenyl(ene), n-nonenyl(ene), 2,2-dimethylheptenyl(ene), 1-ethylpropenyl(ene), 1,1-dimethylpropenyl(ene), isohexenyl(ene), 2-methylpentenyl(ene), 4-methylhexenyl(ene), 5-methylhexenyl(ene), etc. can be mentioned, but it is not limited thereto.In addition, the cycloalkenyl group or cycloalkenylene group specifically includes, but is not limited to, cycloprophenyl(ene), cyclobutenyl(ene), cyclopentenyl(ene), 3-methylcyclopentenyl(ene), 2,3-dimethylcyclopentenyl(ene), cyclohexenyl(ene), 3-methylcyclohexenyl(ene), 4-methylcyclohexenyl(ene), 2,3-dimethylcyclohexenyl(ene), 3,4,5-trimethylcyclohexenyl(ene), 4-tert-butylcyclohexenyl(ene), cycloheptenyl(ene), cyclooctenyl(ene), and the like.

[0025] As used herein, the term alkynyl group or alkynylene group, unless otherwise specified, is a straight-chain or branched acyclic alkynyl group or alkynylene group having 2 to 20 carbon atoms, or 2 to 16 carbon atoms, or 2 to 12 carbon atoms, or 2 to 8 carbon atoms, or 2 to 6 carbon atoms, or a cyclic alkynyl group or alkynylene group having 3 to 20 carbon atoms, or 3 to 16 carbon atoms, or 3 to 12 carbon atoms, or 3 to 8 carbon atoms, or 3 to 6 carbon atoms. Here, when including an alkynyl group or alkynylene group in a ring structure, it corresponds to a cyclic alkynyl group or alkynylene group. Also, for example, ethynyl(ene), n-propynyl(ene), isopropynyl(ene), n-butynyl(ene), isobutynyl(ene), tert-butynyl(ene), sec-butynyl(ene), 1-methyl-butynyl(ene), 1-ethyl-butynyl(ene), n-pentynyl(ene), isopentynyl(ene), neopentynyl(ene), tert-pentynyl(ene), n-hexynyl(ene), 1-methylpentynyl(ene), 2-methylpentynyl(ene), 4-methyl-2-pentynyl(ene), 3,3-dimethylbutynyl(ene), 2-ethylbutynyl(ene), n-heptynyl(ene), 1-methylhexynyl(ene), n-octynyl(ene), tert-octynyl(ene), 1-methylheptynyl(ene), 2-ethylhexynyl(ene), 2-propylpentynyl(ene), n-nonynyl(ene), 2,2-dimethylheptynyl(ene), 1-ethylpropynyl(ene), 1,1-dimethylpropynyl(ene), isohexynyl(ene), 2-methylpentynyl(ene), 4-methylhexynyl(ene), 5-methylhexynyl(ene), etc. can be mentioned, but it is not limited thereto.In addition, the cycloalkynyl group or cycloalkynylene group specifically includes, but is not limited to, cyclopropynyl(ene), cyclobutynyl(ene), cyclopentynyl(ene), 3-methylcyclopentynyl(ene), 2,3-dimethylcyclopentynyl(ene), cyclohexynyl(ene), 3-methylcyclohexynyl(ene), 4-methylcyclohexynyl(ene), 2,3-dimethylcyclohexynyl(ene), 3,4,5-trimethylcyclohexynyl(ene), 4-tert-butylcyclohexynyl(ene), cycloheptynyl(ene), cyclooctynyl(ene), and the like.

[0026] In this specification, the term alkoxy group, unless otherwise specified, means a linear or branched alkoxy group having 1 to 20 carbon atoms, or 1 to 16 carbon atoms, or 1 to 12 carbon atoms, or 1 to 8 carbon atoms, or 1 to 6 carbon atoms or 1 to 4 carbon atoms, or a cyclic alkoxy group having 3 to 20 carbon atoms, or 3 to 16 carbon atoms, or 3 to 12 carbon atoms, or 3 to 8 carbon atoms, or 3 to 6 carbon atoms.

[0027] In this specification, the terms alkylidene group and alkylene group both mean a divalent residue formed by the elimination of two hydrogen atoms from an alkane. However, the alkylidene group means a divalent residue formed by the elimination of two hydrogen atoms from one carbon atom of an alkane, and the alkylene group means a divalent residue formed by the elimination of one hydrogen atom each from two different carbon atoms of an alkane.

[0028] In this specification, the term alkylidene group, unless otherwise specified, means a linear or branched alkylidene group having 1 to 20 carbon atoms, or 1 to 16 carbon atoms, or 1 to 12 carbon atoms, or 1 to 8 carbon atoms, or 1 to 6 carbon atoms or 1 to 4 carbon atoms, or a cyclic alkylidene group having 3 to 20 carbon atoms, or 3 to 16 carbon atoms, or 3 to 12 carbon atoms, or 3 to 8 carbon atoms, or 3 to 6 carbon atoms.

[0029] As used herein, the term "alkylene group" means a linear or branched alkylene group having 2 to 20 carbon atoms, or 2 to 16 carbon atoms, or 2 to 12 carbon atoms, or 2 to 8 carbon atoms, or 2 to 6 carbon atoms, or 2 to 4 carbon atoms, or a cyclic alkylene group having 3 to 20 carbon atoms, or 3 to 16 carbon atoms, or 3 to 12 carbon atoms, or 3 to 8 carbon atoms, or 3 to 6 carbon atoms, unless otherwise specified.

[0030] The alkyl group, alkylene group, alkoxy group, alkylidene group, alkenyl group, alkenylene group, alkynyl group, and alkynylene group may optionally be substituted with at least one substituent. In this case, the substituent may be at least one selected from the group consisting of halogen (chlorine (Cl), iodine (I), bromine (Br), fluorine (F)), aryl group, heteroaryl group, epoxy group, alkoxy group, cyano group, carboxyl group, acryloyl group, methacryloyl group, acryloyloxy group, methacryloyloxy group, carbonyl group, and hydroxy group, but is not limited thereto.

[0031] As used herein, the term "aryl group" means an aromatic ring from which one hydrogen has been removed from an aromatic hydrocarbon ring, and the aromatic hydrocarbon ring may include a monocyclic or polycyclic ring. The aryl group is not particularly limited in terms of the number of carbon atoms, and unless otherwise specified, may be an aryl having 6 to 30 carbon atoms, 6 to 26 carbon atoms, 6 to 22 carbon atoms, 6 to 20 carbon atoms, 6 to 18 carbon atoms, or 6 to 15 carbon atoms. Also, as used herein, the term "arylene group" means that there are two bonding positions on the aryl group, that is, a divalent group. Except that these are each divalent groups, the description of the aryl group described above may be applied. Examples of the aryl group include, but are not limited to, phenyl group, phenylethyl group, phenylpropyl group, benzyl group, tolyl group, xylyl group, or naphthyl group.

[0032] As used herein, the term "heteroaryl group" refers to an aromatic ring containing at least one heteroatom other than carbon. Specifically, the heteroatom may contain at least one atom selected from the group consisting of nitrogen (N), oxygen (O), sulfur (S), selenium (Se), and tellurium (Te). At this time, the atoms constituting the ring structure of the heteroaryl group may also be referred to as reducing atoms. In addition, the heteroaryl group may include a monocyclic or polycyclic ring. The heteroaryl group is not particularly limited in terms of the number of carbon atoms, but unless otherwise specified, it may be a heteroaryl group having 2 to 30 carbon atoms, or 2 to 26 carbon atoms, or 2 to 22 carbon atoms, or 2 to 20 carbon atoms, or 2 to 18 carbon atoms, or 2 to 15 carbon atoms. In other examples, the heteroaryl group is not particularly limited in terms of the number of reducing atoms, but may be a heteroaryl group having 5 to 30, 5 to 25, 5 to 20, 5 to 15, 5 to 10, or 5 to 8 reducing atoms. The heteroaryl group includes, for example, a thiophene group, a furan group, a pyrrole group, an imidazolyl group, a thiazolyl group, an oxazolyl group, an oxadiazolyl group, a triazolyl group, a pyridyl group, a bipyridyl group, a pyrimidyl group, a triazinyl group, an acridyl group, a pyridazinyl group, a pyrazinyl group, a quinolinyl group, a quinazolinyl group, a quinoxalinyl group, a phthalazinyl group, a pyridopyrimidinyl group, a pyridopyrazinyl group, a pyrazinoprazinyl group, an isoquinolinyl group, an indole group, a carbazolyl group, a benzoxazolyl group, a benzimidazolyl group, a benzothiazolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a benzothiophene group, a dibenzothiophene group, a benzofuran group, a dibenzofuran group, a benzosilol group, a dibenzosilol group, a phenanthrolinyl group, an isoxazolyl group, a thiadiazolyl group, a phenothiazinyl group, a phenoxazinyl group, and condensed structures thereof, but is not limited thereto.

[0033] As used herein, the term "heteroarylene group" means that there are two bonding positions on the heteroaryl group, that is, a divalent group. Except that these are each divalent groups, the description of the above-mentioned heteroaryl group may be applicable.

[0034] The aryl group, arylene group, heteroarylene group or heteroaryl group may optionally be substituted with at least one substituent. In this case, the substituent may be at least one selected from the group consisting of halogen (chlorine (Cl), iodine (I), bromine (Br), fluorine (F)), aryl group, heteroaryl group, epoxy group, alkoxy group, cyano group, carboxyl group, acryloyl group, methacryloyl group, acryloyloxy group, methacryloyloxy group, carbonyl group and hydroxy group, but is not limited thereto.

[0035] As used herein, the term amine group means a functional group in which two hydrogen atoms or substituents are bonded to a nitrogen atom having an unshared electron pair. The amine group is divided into a primary amine group in which two hydrogen atoms are bonded to a nitrogen atom having an unshared electron pair, a secondary amine group in which one hydrogen atom and one substituent are bonded to a nitrogen atom having an unshared electron pair, and a tertiary amine group in which two substituents are bonded to a nitrogen atom having an unshared electron pair. At this time, the substituent may be at least one selected from the group consisting of alkyl group, alkenyl group, alkynyl group, halogen (chlorine (Cl), iodine (I), bromine (Br), fluorine (F)), aryl group, heteroaryl group, epoxy group, alkoxy group, cyano group, carboxyl group, acryloyl group, methacryloyl group, acryloyloxy group, methacryloyloxy group, carbonyl group and hydroxy group, but is not limited thereto.

[0036] The curable composition may contain an isocyanate compound, a filler component and a plasticizer.

[0037] As used herein, the term curable composition means the curable composition described above. The curable composition may contain components that can be converted into a polymer through physical or chemical reactions such as a curing reaction or a polymerization reaction, as well as components generally known as polymers. The curable composition may have so-called adhesive performance and / or tack performance before or after curing.

[0038] The curable composition may be a solvent-based curable composition, an aqueous curable composition, or a solvent-free curable composition. Further, the curable composition may be an active energy ray (e.g., ultraviolet ray) curable type, a moisture curable type, a heat curable type, or a room temperature curable type. When the curable composition is of the active energy ray curable type, the curing of the curable composition is carried out by irradiation with active energy rays such as ultraviolet rays. In the case of the moisture curable type, the curing of the curable composition is carried out by a method of maintaining it under appropriate moisture. In the case of the heat curable type, the curing of the curable composition is carried out by a method of applying appropriate heat. Or in the case of the room temperature curable type, the curing of the curable composition may be carried out by a method of maintaining the curable composition at room temperature.

[0039] The curable composition according to an example of the present application may be a one-component curable composition or a two-component curable composition, and in some cases, it may be any part of the two-component curable composition.

[0040] As is well known, the term one-component curable composition used in the present application means a composition in which all the components necessary for curing are present in a mixed state and which cures when specific conditions (e.g., specific temperature or ultraviolet ray irradiation, etc.) are satisfied. Further, the term two-component curable composition used in the present application means a composition in which the components necessary for curing are present in a physically separated state (e.g., separation into a main agent part and a curing agent part), and which cures when the separated components are mixed and exposed to a curable environment.

[0041] The curable composition according to an example of the present application may contain an isocyanate compound as described above. In the present specification, the term "isocyanate compound" means a compound having at least one isocyanate group. In the present specification, the term "diisocyanate compound" means a compound having at least two of the isocyanate groups. In the present specification, the term "polyisocyanate compound" means a compound having at least three of the isocyanate groups. The lower limit of the number of isocyanate groups that the polyisocyanate compound has may be 3, and the upper limit thereof may be 10, 9, 8, 7, 6, 5, 4, or 3. The number of the isocyanate groups is within a range that is equal to or greater than any of the lower limits described above or exceeds them, within a range that is equal to or less than any of the upper limits described above or is less than them, or within a range that is equal to or greater than any of the lower limits described above or exceeds them while being equal to or less than any of the upper limits described above or is less than them.

[0042] The isocyanate compound may be used without particular limitation as long as it is commonly used in the industry (for example, those commonly used for the formation of polyurethanes). For example, the diisocyanate compound may be an aromatic diisocyanate compound such as tolylene diisocyanate, diphenylmethane diisocyanate, phenylene diisocyanate, polyethylene phenylene polyisocyanate, xylene diisocyanate, tetramethylxylylene diisocyanate, tolidine diisocyanate, naphthalene diisocyanate and / or triphenylmethane triisocyanate, and / or a chain diisocyanate compound such as hexamethylene diisocyanate, trimethylhexamethylene diisocyanate, lysine diisocyanate, norbornane diisocyanate methyl, ethylene diisocyanate, propylene diisocyanate and / or tetramethylene diisocyanate, and an aliphatic diisocyanate compound containing an alicyclic diisocyanate compound such as trans-cyclohexane-1,4-diisocyanate, isophorone diisocyanate, bis(isocyanatomethyl)cyclohexane diisocyanate and / or dicyclohexylmethane diisocyanate. As the diisocyanate compound, one or a mixture of two or more of the above-mentioned types may be used.

[0043] As the polyisocyanate compound, at least one selected from the group consisting of isocyanates in which one or more of the above-mentioned diisocyanate compounds are added to a polyol compound, multimers of the diisocyanate compounds, and biuret compounds may be used. For example, an adduct of the aromatic diisocyanate compound to the polyol, an aromatic polyisocyanate compound that is the multimer or biuret compound, and / or an adduct of the aliphatic diisocyanate compound to the polyol, an aliphatic polyisocyanate compound that is the multimer and / or biuret compound may be used. As the polyisocyanate compound, one or a mixture of two or more of the above-mentioned types may be used.

[0044] In the curable composition according to an example of the present application, as the isocyanate compound, an aliphatic isocyanate compound may be used. The isocyanate compound of the curable composition may not contain an aromatic isocyanate compound and may contain only an aliphatic isocyanate compound. By using only an aliphatic isocyanate compound as the isocyanate compound, it can be advantageous for ensuring physical properties with excellent compatibility when blended with a filler component described later and with little change in viscosity over time.

[0045] In the curable composition according to an example of the present application, the isocyanate compound may contain a diisocyanate compound and a polyisocyanate compound. When the diisocyanate compound and the polyisocyanate compound are mixed and used in an appropriate ratio, it can be advantageous for ensuring physical properties with excellent compatibility when blended with a filler component described later and with little change in viscosity over time. Here, the diisocyanate compound may be an aliphatic diisocyanate compound, and the polyisocyanate compound may be an aliphatic polyisocyanate compound. Through such a combination, it can be advantageous for ensuring physical properties with excellent compatibility when blended with a filler component described later and with little change in viscosity over time. In the present specification, the term aliphatic diisocyanate compound means a diisocyanate compound that does not contain an aromatic functional group in its molecular structure, and the aliphatic polyisocyanate compound means a polyisocyanate compound that does not contain an aromatic functional group in its molecular structure. Examples of the aliphatic diisocyanate compound and examples of the aliphatic polyisocyanate compound are as described above.

[0046] The lower limit of the molecular weight or weight-average molecular weight of the diisocyanate compound contained in the isocyanate compound of the curable composition according to an example of the present application may be about 100 g / mol, 110 g / mol, 120 g / mol, 130 g / mol, 140 g / mol, 150 g / mol, 160 g / mol or 170 g / mol, and the upper limit thereof may be about 300 g / mol, 280 g / mol, 260 g / mol, 240 g / mol, 220 g / mol, 200 g / mol or 180 g / mol. The molecular weight or weight-average molecular weight is within the range that is equal to or greater than any of the lower limits described above or exceeds them, within the range that is equal to or less than any of the upper limits described above or less than them, or within the range that is equal to or greater than any of the lower limits described above or exceeds them while being equal to or less than any of the upper limits described above or less than them.

[0047] Further, the lower limit of the molecular weight or weight-average molecular weight of the polyisocyanate compound contained in the curable composition according to an example of the present application may be about 600 g / mol, 620 g / mol, 640 g / mol, 660 g / mol, 680 g / mol, 700 g / mol, 720 g / mol, 740 g / mol, 760 g / mol, 780 g / mol or 800 g / mol, and the upper limit thereof may be about 1,000 g / mol, 980 g / mol, 960 g / mol, 940 g / mol, 920 g / mol, 900 g / mol, 880 g / mol, 860 g / mol or 840 g / mol. The molecular weight or weight-average molecular weight is within the range that is equal to or greater than any of the lower limits described above or exceeds them, within the range that is equal to or less than any of the upper limits described above or less than them, or within the range that is equal to or greater than any of the lower limits described above or exceeds them while being equal to or less than any of the upper limits described above or less than them. When such components are blended with the filler components described later, it can be advantageous for ensuring physical properties with excellent blendability and little change in viscosity over time. Here, the molecular weight or weight-average molecular weight may be measured by the GPC described above.

[0048] When the isocyanate compound contains the diisocyanate compound and the polyisocyanate compound simultaneously, the lower limit of the weight ratio of the polyisocyanate compound to 100 parts by weight of the diisocyanate compound may be about 1 part by weight, 10 parts by weight, 20 parts by weight, 30 parts by weight, 40 parts by weight, 50 parts by weight, 60 parts by weight, 70 parts by weight, 80 parts by weight, 90 parts by weight or 100 parts by weight, and the upper limit thereof may be about 1000 parts by weight, 900 parts by weight, 800 parts by weight, 700 parts by weight, 600 parts by weight, 500 parts by weight, 400 parts by weight, 300 parts by weight, 200 parts by weight, 150 parts by weight or 100 parts by weight. The weight ratio is within the range that is equal to or more than any of the lower limits described above or exceeds the lower limit, within the range that is equal to or less than any of the upper limits described above or is less than the upper limit, or within the range that is equal to or more than any of the lower limits described above or exceeds the lower limit while being equal to or less than any of the upper limits described above or is less than the upper limit.

[0049] The curable composition according to an example of the present application may contain a filler component as described above. Through the filler component, thixotropy can be ensured and / or heat dissipation (thermal conductivity) can be ensured in a battery module or a battery pack as required in the process. The term "filler component" means a component consisting only of a filler.

[0050] In the curable composition according to an example of the present application, the lower limit of the weight ratio of the filler component may be about 70 wt%, 70 wt%, 71 wt%, 72 wt%, 73 wt%, 74 wt%, 75 wt%, 76 wt%, 77 wt%, 78 wt%, 79 wt%, 80 wt%, 81 wt%, 82 wt%, 83 wt%, 84 wt%, 85 wt%, 86 wt% or 87 wt% with respect to the total weight of the composition, and the upper limit thereof may be about 99 wt%, 98 wt%, 97 wt%, 96 wt%, 95 wt%, 94 wt%, 93 wt%, 92 wt%, 91 wt%, 90 wt%, 89 wt%, 88 wt% or 87 wt%. The weight ratio is within the range that is equal to or greater than any of the lower limits described above or exceeds the lower limits, within the range that is equal to or less than any of the upper limits described above or is less than the upper limits, or within the range that is equal to or greater than any of the lower limits described above or exceeds the lower limits while being equal to or less than any of the upper limits described above or is less than the upper limits.

[0051] The filler component of the curable composition according to an example of the present application may contain a heat conductive filler or be a heat conductive filler component. The term heat conductive filler component or heat conductive filler means a filler component or filler when the curable composition or its cured product exhibits the heat conductivity described below through the filler. The heat conductivity of such a filler or filler component may be, for example, about 1 W / m·K or more, about 5 W / m·K or more, about 10 W / m·K or more or about 15 W / m·K or more, or may be about 400 W / m·K or less, about 350 W / m·K or less or about 300 W / m·K or less.

[0052] Examples of the heat conductive filler include, but are not limited to, oxide fillers such as aluminum oxide (alumina), magnesium oxide, beryllium oxide, or titanium oxide; nitride fillers such as boron nitride, silicon nitride, or aluminum nitride; carbide fillers such as silicon carbide; hydroxide fillers such as aluminum hydroxide or magnesium hydroxide; metal fillers such as copper, silver, iron, aluminum, or nickel; metal alloy fillers such as titanium; or silicon powders such as quartz, glass, or silica. Also, considering the ensuring of insulation properties, the application of carbon fillers such as graphite or activated carbon may also be considered.

[0053] The filler component of the curable composition according to an example of the present application may use one or more appropriately selected as needed, and the form and ratio are not particularly limited, and may be selected in consideration of the viscosity of the curable composition, the possibility of sedimentation in the cured product, the desired thermal resistance or thermal conductivity, insulation properties, filling effect, or dispersibility. Also, fillers of the same type may be used, or those with different shapes or different average particle sizes may be mixed and used. For example, aluminum hydroxide, aluminum, and alumina may be mixed and used, and their respective shapes and average particle sizes may be different from each other.

[0054] In this specification, the term average particle size refers to the so-called D50 particle size (median particle size), which means the particle size at 50% cumulative volume basis of the particle size distribution. That is, the particle size distribution is determined on a volume basis, and the particle size at the point where the cumulative value becomes 50% in the cumulative curve with the total volume as 100% can be referred to as the average particle size. The D50 particle size as described above may be measured by the laser diffraction method.

[0055] On the one hand, the shape of the filler contained in the filler component of the curable composition according to an example of the present application may be appropriately selected and used as needed from spherical and / or non-spherical (for example, angular and needle-like shapes, etc.), and is not limited thereto. The term "spherical filler" in this specification means a filler having a sphericity of about 0.9 or more or 0.95 or more, and a non-spherical or angular filler means a filler having a sphericity of less than 0.95 or less than 0.9. The sphericity can be confirmed through particle size analysis of the filler. Specifically, the sphericity of a filler that is a three-dimensional particle is defined as the ratio (S' / S) of the surface area (S) of the particle to the surface area (S') of a sphere having the same volume as the particle. For an actual filler, generally circularity is used. The circularity is obtained by obtaining a two-dimensional image of the actual filler and representing it as the ratio of the boundary of a circle having the same area (A) as the image to the boundary of the image, and is obtained by the following mathematical formula.

[0056] <Circularity mathematical formula> Circularity = 4πA / P 2

[0057] The circularity is represented by a value from 0 to 1. A perfect circle has a value of 1, and the more irregular the shape of the particle, the lower the value will be compared to 1. The sphericity value in this specification was taken as the average value of the circularity measured by a particle analysis instrument (FPIA-3000) manufactured by Malvern.

[0058] The filler component of the curable composition according to an example of the present application may essentially contain a hydroxide filler in order to achieve the object. Since such a filler is a relatively low specific gravity filler, it is advantageous from the aspect of weight reduction. For example, the lower limit of the weight ratio of the hydroxide filler based on the total weight of the filler component may be about 30 wt%, 32 wt%, 34 wt%, 36 wt%, 38 wt%, 40 wt%, 42 wt%, 44 wt%, 46 wt%, 48 wt%, 50 wt%, 52 wt%, 54 wt%, 56 wt%, 58 wt% or 60 wt%, and the upper limit thereof may be about 80 wt%, 78 wt%, 76 wt%, 74 wt%, 72 wt%, 70 wt%, 68 wt%, 66 wt%, 64 wt% or 62 wt%. The weight ratio is within a range that is equal to or greater than any of the lower limits described above, within a range that is equal to or less than any of the upper limits described above, or within a range that is equal to or greater than any of the lower limits described above while being equal to or less than any of the upper limits described above.

[0059] The upper limit of the specific gravity of the hydroxide filler at room temperature may be about 3, 2.9, 2.8, 2.7, 2.6 or 2.5, and the lower limit thereof may be about 1. The specific gravity is within a range that is equal to or greater than any of the lower limits described above, within a range that is equal to or less than any of the upper limits described above, or within a range that is equal to or greater than any of the lower limits described above while being equal to or less than any of the upper limits described above.

[0060] By including a hydroxide filler having the specific gravity range described above within the content ratio range, the filler component can ensure excellent compatibility as well as low density characteristics. The hydroxide filler may be a heat conductive filler, and the examples are as described above.

[0061] The filler component of the curable composition according to an example of the present application may include a first hydroxide filler and a second hydroxide filler having different average particle sizes as hydroxide fillers. For example, the lower limit of the average particle size of the first hydroxide filler may be about 60 μm, 61 μm, 62 μm, 63 μm, 64 μm, 65 μm, 66 μm, 67 μm, 68 μm, 69 μm or 70 μm, and the upper limit thereof may be about 200 μm, 190 μm, 180 μm, 170 μm, 160 μm or 150 μm. The average particle size is within a range that is equal to or greater than any one of the lower limits described above, within a range that is equal to or less than any one of the upper limits described above, or within a range that is equal to or greater than any one of the lower limits described above while being equal to or less than any one of the upper limits described above. Further, the upper limit of the average particle size of the second hydroxide filler may be about 10 μm, 9 μm, 8 μm, 7 μm, 6 μm, 5 μm, 4 μm, 3 μm or 2 μm, and the lower limit thereof may be about 0.01 μm, 0.05 μm, 0.1 μm or 0.5 μm. The average particle size is within a range that is equal to or greater than any one of the lower limits described above, within a range that is equal to or less than any one of the upper limits described above, or within a range that is equal to or greater than any one of the lower limits described above while being equal to or less than any one of the upper limits described above. By the filler component of the curable composition containing two types of hydroxide fillers having different average particle sizes as described above, excellent compatibility can be ensured. In one example, the first hydroxide filler may be the filler having the largest average particle size among all the hydroxide fillers contained in the filler component, and the second hydroxide filler may be the filler having the smallest average particle size among all the hydroxide fillers contained in the filler component.

[0062] The filler component of the curable composition according to an example of the present application may include the first hydroxide filler and the second hydroxide filler as hydroxide fillers. The lower limit of the weight ratio (HF1 / HF2) of the first hydroxide filler (HF1) to the second hydroxide filler (HF2) may be about 0.1, 0.2, 0.3, 0.4, 0.5, 0.6, 0.7, 0.8, 0.9, 1, 1.1, 1.2, 1.3, 1.4, 1.5, 1.6, 1.7, 1.8, 1.9 or 2, and the upper limit thereof may be about 10, 9.5, 9, 8.5, 8, 7.5, 7, 6.5, 6, 5.5, 5, 4.5, 4, 3.5, 3, 2.5 or 2. The weight ratio is within a range that is equal to or greater than any of the lower limits described above or exceeds them, within a range that is equal to or less than any of the upper limits described above or is less than them, or within a range that is equal to or greater than any of the lower limits described above or exceeds them while being equal to or less than any of the upper limits described above or is less than them. By including two kinds of hydroxide fillers having different average particle sizes in the above weight ratio as the filler component of the curable composition, excellent compatibility can be ensured.

[0063] The filler component of the curable composition according to an example of the present application may include the first hydroxide filler and the second hydroxide filler as hydroxide fillers. The lower limit of the average particle size ratio (DHF1 / DHF2) of the first hydroxide filler (DHF1) to the second hydroxide filler (DHF2) may be about 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29 or 30, and the upper limit thereof may be about 100, 95, 90, 85, 80, 75, 70, 65, 60, 55, 50, 49, 48, 47, 46, 45, 44, 43, 42, 41, 40, 39, 38, 37, 36 or 35. The ratio may be within the range that is equal to or greater than any of the lower limits described above, within the range that is equal to or less than any of the upper limits described above, or within the range that is equal to or greater than any of the lower limits described above while being equal to or less than any of the upper limits described above. By including two kinds of hydroxide fillers having different average particle sizes in the filler component of the curable composition in the above average particle size ratio, excellent compatibility can be ensured.

[0064] The filler component of the curable composition according to an example of the present application may further include a non-hydroxide filler (or also referred to as an additional filler) together with the hydroxide filler in order to achieve the object. The term non-hydroxide filler means a filler that is not a hydroxide. At least one selected from the group consisting of an oxide filler, a nitride filler, a carbide filler, a metal filler, an alloy filler, silicon powder, and a carbon filler may be used as the additional filler, and the specific types thereof are as described above.

[0065] In one example, in the filler component, the lower limit of the content of the non-hydroxide filler with respect to 100 parts by weight of the hydroxide filler may be about 10 parts by weight, 15 parts by weight, 20 parts by weight, 25 parts by weight, 30 parts by weight, 35 parts by weight, 40 parts by weight, 45 parts by weight, 50 parts by weight, 55 parts by weight, 60 parts by weight or 65 parts by weight, and the upper limit thereof may be about 200 parts by weight, 190 parts by weight, 180 parts by weight, 170 parts by weight, 160 parts by weight, 150 parts by weight, 140 parts by weight, 130 parts by weight, 120 parts by weight, 110 parts by weight, 100 parts by weight, 90 parts by weight, 80 parts by weight or 70 parts by weight. The ratio is within the range that is equal to or greater than any of the lower limits described above or exceeds them, within the range that is equal to or less than any of the upper limits described above or is less than them, or within the range that is equal to or greater than any of the lower limits described above or exceeds them while being equal to or less than any of the upper limits described above or is less than them.

[0066] The lower limit of the specific gravity of the non-hydroxide filler at room temperature may be about 3, 3.1, 3.2, 3.3, 3.4, 3.5, 3.6, 3.7, 3.8 or 3.9, and the upper limit thereof may be about 10. The specific gravity is within the range that is equal to or greater than any of the lower limits described above or exceeds them, within the range that is equal to or less than any of the upper limits described above or is less than them, or within the range that is equal to or greater than any of the lower limits described above or exceeds them while being equal to or less than any of the upper limits described above or is less than them. By including the additional filler within the content ratio range, the filler component can ensure appropriate thixotropic properties, hardness viscosity and thermal conductivity characteristics in terms of process. The additional filler may be a thermally conductive filler, and the respective examples are as described above.

[0067] The filler component of the curable composition according to an example of the present application may further include an additional filler simultaneously with the hydroxide filler in order to achieve the object, and the additional filler may be at least one selected from the group consisting of an oxide filler, a nitride filler, a carbide filler, a metal filler, an alloy filler, silicon powder, and a carbon filler. When included, the average particle size of the additional filler may be in the range of 10 μm to 60 μm. For example, the lower limit of the weight ratio (HF1 / AF) of the first hydroxide filler (HF1) to the additional filler (AF) in the filler component may be about 0.5, 0.6, 0.7, 0.8, 0.9, or 1, and the upper limit may be about 20, 18, 16, 14, 12, 10, 8, 6, 4, 2, 1.5, or 1. The ratio may be within a range that is equal to or greater than any of the lower limits described above, within a range that is equal to or less than any of the upper limits described above, or within a range that is equal to or greater than any of the lower limits described above while being equal to or less than any of the upper limits described above. Even while the filler component further includes an additional filler having the average particle size, by satisfying the range of the weight ratio with the first hydroxide filler, appropriate thixotropic properties, viscosity, and thermal conductivity characteristics can be ensured. Also, the lower limit of the average particle size ratio (DHF1 / DAF) of the first hydroxide filler (DHF1) to the additional filler (DAF) in the filler component may be about 1, 1.2, 1.4, 1.6, 1.8, 2, 2.2, 2.4, 2.6, 2.8, 3, 3.2, or 3.4, and the upper limit may be about 5, 4.8, 4.6, 4.4, 4.2, 4, 3.8, or 3.6. The ratio may be within a range that is equal to or greater than any of the lower limits described above, within a range that is equal to or less than any of the upper limits described above, or within a range that is equal to or greater than any of the lower limits described above while being equal to or less than any of the upper limits described above.While the filler component further includes an additional filler having the average particle size, by satisfying the range of the average particle size ratio with the first hydroxide filler, appropriate thixotropic properties, viscosity, and thermal conductivity characteristics can be ensured in the process.

[0068] In one example, when the filler component includes a hydroxide filler (DHF) and the additional filler (DAF), the lower limit of the ratio (A / B) of the average particle size (A) of the hydroxide filler (DHF) to the average particle size (B) of the additional filler may be about 1, 1.2, 1.4, 1.6, 1.8, 2, 2.1, 2.2, or 2.3, and the upper limit thereof may be about 5, 4.8, 4.6, 4.4, 4.2, 4, 3.8, 3.6, 3.4, 3.2, 3.0, 2.8, 2.6, 2.5, or 2.5. The ratio is within the range that is equal to or greater than any of the lower limits described above or exceeds them, within the range that is equal to or less than any of the upper limits described above or is less than them, or within the range that is equal to or greater than any of the lower limits described above or exceeds them while being equal to or less than any of the upper limits described above or is less than them. In the above, the average particle sizes of the hydroxide filler and the additional filler are the weighted averages of their respective average particle sizes. For example, when the filler component includes, as a hydroxide filler, filler (A) with an average particle size of D1 and filler (B) with an average particle size of D2, and the weight ratio between the fillers is W1:W2 (A:B), the weighted average can be calculated as (D1×W1 + D2×W2) / (W1 + W2), and the same applies to the case of the additional filler. While the filler component further includes an additional filler having the average particle size, by satisfying the range of the average particle size ratio with the hydroxide filler, appropriate thixotropic properties, viscosity, and thermal conductivity characteristics can be ensured in the process.

[0069] The curable composition according to an example of the present application may contain a plasticizer as described above. The curable composition according to an example of the present application may contain a plasticizer in an appropriate proportion in order to improve the problems of storage stability and deterioration of compatibility due to the isocyanate groups present in the isocyanate compound and the moisture and / or hydroxyl groups of the filler component. As described above, by containing a plasticizer in an appropriate proportion, it is possible to secure a curable composition having a low viscosity increase rate over time and excellent compatibility. Further, despite the application of the plasticizer, it is possible to form a cured product having an appropriate hardness.

[0070] In the curable composition according to an example of the present application, as the plasticizer, at least one selected from the group consisting of phthalic acid compounds, phosphoric acid compounds, adipic acid compounds, sebacic acid compounds, citric acid compounds, glycolic acid compounds, trimellitic acid compounds, polyester compounds, epoxidized soybean oil, chlorinated paraffin, chlorinated fatty acid esters, fatty acid compounds, and vegetable oils may be used. For example, as the phthalic acid compound, at least one of dimethyl phthalate, diethyl phthalate, dibutyl phthalate, dihexyl phthalate, di-n-octyl phthalate, di-2-ethylhexyl phthalate, diisooctyl phthalate, dicapryl phthalate, dinonyl phthalate, diisononyl phthalate, didecyl phthalate, diundecyl phthalate, dilauryl phthalate, ditridecyl phthalate, dibenzyl phthalate, dicyclohexyl phthalate, butyl benzyl phthalate, octyl decyl phthalate, butyl octyl phthalate, octyl benzyl phthalate, n-hexyl n-decyl phthalate, n-octyl phthalate, and n-decyl phthalate may be used. Further, as the phosphoric acid compound, at least one of tricresyl phosphate, trioctyl phosphate, triphenyl phosphate, octyl diphenyl phosphate, cresyl diphenyl phosphate, and trichloroethyl phosphate may be used. Further, as the adipic acid compound, at least one of dibutoxyethoxyethyl adipate (DBEEA), dioctyl adipate, diisooctyl adipate, di-n-octyl adipate, didecyl adipate, diisodecyl adipate, dinonyl adipate, diisononyl adipate, n-octyl n-decyl adipate, n-heptyl adipate, and n-nonyl adipate may be used. Further, as the sebacic acid compound, at least one of dibutyl sebacate, dioctyl sebacate, diisooctyl sebacate, and butyl benzyl may be used. Further, as the citric acid compound, at least one of triethyl citrate, acetyl triethyl citrate, tributyl citrate, acetyl tributyl citrate, and acetyl trioctyl citrate may be used.Further, as the glycolic acid compound, at least one of methyl phthalyl ethyl glycolate, ethyl phthalyl ethyl glycolate, and butyl phthalyl ethyl glycolate may be used. Further, as the trimellitic acid compound, at least one of trioctyl trimellitate and tri-n-octyl n-decyl trimellitate may be used.

[0071] Considering the combination with the isocyanate compound and the filler component and the object of the present application, the curable composition according to an example of the present application may contain at least one selected from the group consisting of phthalic acid compounds and adipic acid compounds as the plasticizer.

[0072] In order to achieve appropriate effects, as the plasticizer, a non-reactive ester compound among the above-described types may be used. The term "non-reactive" means that the compound is not reactive with the isocyanate compound contained in the curable composition, and the ester compound means a compound having at least one ester bond.

[0073] The lower limit of the number of the ester bonds contained in the non-reactive ester compound may be about 1 or 2, and the upper limit may be about 10, 9, 8, 7, 6, 5, 4, 3, or 2. The number of the ester bonds is within a range that is equal to or more than any of the above-described lower limits or exceeds the lower limit, within a range that is equal to or less than any of the above-described upper limits or less than the upper limit, or within a range that is equal to or more than any of the above-described lower limits or exceeds the lower limit while being equal to or less than any of the above-described upper limits or less than the upper limit.

[0074] Also, in the non-reactive ester compound, one end of the ester bond may be linked to an aromatic structure. At this time, the lower limit of the number of carbon atoms in the aromatic structure may be 6, and the upper limit may be about 20, 18, 16, 14, 12, 10, 8 or 6. The number of carbon atoms is within the range that is equal to or more than any of the lower limits described above or exceeds them, within the range that is equal to or less than any of the upper limits described above or less than them, or within the range that is equal to or more than any of the lower limits described above or exceeds them while being equal to or less than any of the upper limits described above or less than them.

[0075] In the non-reactive ester compound, the other end of the ester bond (the other end not linked to the aromatic structure) may be linked to an alkyl group, an alkenyl group or an alkynyl group. At this time, the lower limit of the number of carbon atoms in each of the alkyl group, alkenyl group or alkynyl group may be 6, 7, 8 or 9, and the upper limit may be about 30, 28, 26, 24, 22, 20, 18, 16, 14, 12 or 10. The number of carbon atoms is within the range that is equal to or more than any of the lower limits described above or exceeds them, within the range that is equal to or less than any of the upper limits described above or less than them, or within the range that is equal to or more than any of the lower limits described above or exceeds them while being equal to or less than any of the upper limits described above or less than them. The alkyl group, alkenyl group or alkynyl group may be linear, branched or cyclic, and appropriately may be linear or branched or branched.

[0076] The lower limit of the molecular weight (molar mass or weight-average molecular weight) of the non-reactive ester compound may be about 200 g / mol, 250 g / mol, 300 g / mol, 350 g / mol or 400 g / mol, and the upper limit thereof may be about 2000 g / mol, 1500 g / mol, 1000 g / mol, 900 g / mol, 800 g / mol, 700 g / mol, 600 g / mol, 500 g / mol or 450 g / mol. The molecular weight is within a range that is equal to or greater than any of the lower limits described above, within a range that is equal to or less than any of the upper limits described above, or within a range that is equal to or greater than any of the lower limits described above while being equal to or less than any of the upper limits described above. The alkyl group, alkenyl group or alkynyl group may be linear, branched or cyclic, and appropriately may be linear or branched or branched.

[0077] The lower limit of the weight ratio of the plasticizer to 100 parts by weight of the isocyanate compound may be about 0.1 part by weight, 0.5 part by weight, 1 part by weight, 1.5 part by weight, 2 parts by weight, 2.5 parts by weight, 3 parts by weight, 3.5 parts by weight, 4 parts by weight, 4.5 parts by weight or 5 parts by weight, and the upper limit thereof may be about 15 parts by weight, 14.5 parts by weight, 14 parts by weight, 13.5 parts by weight, 13 parts by weight, 12.5 parts by weight, 12 parts by weight, 11.5 parts by weight, 11 parts by weight, 10.5 parts by weight or 10 parts by weight. The ratio is within a range that is equal to or greater than any of the lower limits described above, within a range that is equal to or less than any of the upper limits described above, or within a range that is equal to or greater than any of the lower limits described above while being equal to or less than any of the upper limits described above. By adjusting the plasticizer at the above content ratio, the curable composition can ensure a cured product having excellent levels of surface hardness and thermal conductivity, a low viscosity increase rate due to changes over time, and a curable composition excellent in compatibility.

[0078] In a curable composition according to an example of the present application, the lower limit of the weight ratio of the plasticizer to 100 parts by weight of the filler component may be about 0.1 part by weight, 0.15 part by weight, 0.2 part by weight, 0.25 part by weight, 0.3 part by weight, 0.35 part by weight, 0.4 part by weight, 0.45 part by weight or 0.5 part by weight, and the upper limit thereof may be about 1.5 parts by weight, 1.45 parts by weight, 1.4 parts by weight, 1.35 parts by weight, 1.3 parts by weight, 1.25 parts by weight, 1.2 parts by weight, 1.15 parts by weight or 1.1 parts by weight. The ratio is within the range that is equal to or greater than any of the lower limits described above, within the range that is equal to or less than any of the upper limits described above, or within the range that is equal to or greater than any of the lower limits described above while being equal to or less than any of the upper limits described above. By adjusting the plasticizer at the content ratio, the curable composition can ensure a cured product having excellent levels of surface hardness and thermal conductivity, have a low viscosity increase rate over time, and ensure a curable composition with excellent compatibility.

[0079] In a curable composition according to an example of the present application, the lower limit of the weight ratio of the plasticizer to 100 parts by weight of the hydroxide filler as the filler component may be about 0.5 part by weight, 0.55 part by weight, 0.6 part by weight, 0.65 part by weight, 0.7 part by weight, 0.75 part by weight, 0.8 part by weight, 0.85 part by weight or 0.9 part by weight, and the upper limit thereof may be about 10 parts by weight, 9 parts by weight, 8 parts by weight, 7 parts by weight, 6 parts by weight, 5 parts by weight, 4 parts by weight, 3 parts by weight or 2 parts by weight. The ratio is within the range that is equal to or greater than any of the lower limits described above, within the range that is equal to or less than any of the upper limits described above, or within the range that is equal to or greater than any of the lower limits described above while being equal to or less than any of the upper limits described above. By considering the combination of the plasticizer with the hydroxide filler and adjusting at the content ratio, the curable composition can ensure a cured product having excellent levels of surface hardness and thermal conductivity, have a low viscosity increase rate over time, and ensure a curable composition with excellent compatibility.

[0080] The curable composition according to an example of the present application can help ensure desired physical properties by further containing an additional compound as necessary. By containing at least one of the ones mentioned below, the additional compound can help the present application ensure desired physical properties.

[0081] The curable composition according to an example of the present application may further contain a viscosity modifier, for example, a viscosity modifier for adjusting the viscosity as needed, such as increasing or decreasing the viscosity, or adjusting the viscosity by shear force, for example, a thixotropy imparting agent, a diluent, a surface treatment agent or a coupling agent. The thixotropy imparting agent can adjust the viscosity of the curable composition by shear force. Examples of usable thixotropy imparting agents include fumed silica. The diluent is usually used to lower the viscosity of the curable composition, and various types known in the art may be used without limitation as long as they can exhibit the above-described effects. The surface treatment agent is for surface treatment of the filler introduced into the cured product of the curable composition, and various types known in the art may be used without limitation as long as they can exhibit the above-described effects. In the case of a coupling agent, for example, it may be used to improve the dispersibility between the filler component and other components, and various types known in the art may be used without limitation as long as they can exhibit the above-described effects. Further, the curable composition according to an example of the present application may further contain a flame retardant or a flame retardant aid as needed. The curable composition further containing a flame retardant or a flame retardant aid can be cured to form a flame retardant resin. As the flame retardant, various known flame retardants may be applied without particular limitation, and for example, a solid-phase filler-like flame retardant or a liquid flame retardant may be applied. Examples of the flame retardant include, but are not limited to, organic flame retardants such as melamine cyanurate and inorganic flame retardants such as magnesium hydroxide. When the amount of the thermally conductive filler contained in the curable composition is large, a liquid type flame retardant material (such as TEP, triethyl phosphate or TCPP, tris(1,3-chloro-2-propyl)phosphate) may be used. Further, a silane coupling agent that can act as a flame retardancy enhancer may be added. Further, the curable composition according to an example of the present application may further use a dispersant as needed to improve the dispersibility, and various types known in the art may be used without limitation as the dispersant, and for example, a polyester dispersant may be used.In addition, for the curable composition according to an example of the present application, a moisture absorbent may be used as necessary. The moisture absorbent may be used without limitation as long as it is for minimizing the influence of the isocyanate compound on moisture. For example, a siloxane compound or the like may be used.

[0082] The density of the curable composition according to an example of the present application, measured at room temperature (about 25°C), may have an upper limit of about 2.5 g / mL, 2.49 g / mL, 2.48 g / mL, 2.47 g / mL, 2.46 g / mL, 2.45 g / mL, 2.44 g / mL, 2.43 g / mL, 2.42 g / mL, 2.41 g / mL or 2.4 g / mL, and its lower limit may be about 1 g / mL. The density is within a range that is less than or below any of the above upper limits, and is greater than or exceeds any of the above lower limits, but is less than or below any of the above upper limits. The curable composition can ensure low-density characteristics as described above by combining the above-mentioned isocyanate compound, filler component and plasticizer. Further, the density may be specifically measured according to the density measurement items of the examples described later.

[0083] The curable composition according to an example of the present application may have a viscosity change rate (V R ) within a predetermined range. For example, the upper limit of the viscosity change rate (V R ) may be about 15%, 14%, 13%, 12%, 11%, 10%, 9%, 8%, 7%, 6%, 5%, 4.9%, 4.8%, 4.7%, 4.6% or 4.5%, and its lower limit may be about 0%, 1%, 2%, 3%, 4% or 5%. The viscosity change rate is within a range that is less than or below any of the above upper limits, or is greater than or exceeds any of the above lower limits, but is less than or below any of the above upper limits.

[0084] [Equation 1] V R = 100×|V f-V i | / V i (General formula 1)

[0085] In general formula 1, V i is the initial viscosity of the curable composition measured at a shear rate of 1.2 rpm at room temperature, and V f is the viscosity of the curable composition measured at a shear rate of 1.2 rpm at room temperature after maintaining at room temperature for 240 hours from the time when the above V i was measured. The method for measuring the viscosity is described in the items of the examples in this specification.

[0086] The curable composition may have a low viscosity change rate over time as described above by combining the isocyanate compound, filler component, and plasticizer described above. The curable composition according to an example of the present application contains an excessive amount of hydroxide filler to ensure low density characteristics, but based on an appropriate combination of the isocyanate compound and the plasticizer, the viscosity change rate over time can be reduced.

[0087] The curable composition according to an example of the present application may be formed by mixing each of the above-listed components. Further, the curable composition according to an example of the present application is not particularly limited with respect to the mixing order as long as all necessary components are included. However, when blending the filler component and the isocyanate compound, the filler particles having the smallest average particle size may be first blended to produce a primary mixture, and the primary mixture may be further blended with filler particles having different average particle sizes to produce a secondary mixture.

[0088] Specifically, the method for producing the curable composition according to an example of the present application may include a step of mixing an isocyanate compound, a second hydroxide filler, and a plasticizer to produce a primary mixture, and a step of further adding and mixing the first hydroxide filler to the primary mixture to produce a secondary mixture. Here, in the step of producing the secondary mixture, the first hydroxide filler and the additional filler may be further added to the primary mixture.

[0089] When producing the curable composition by the above method, it is possible to minimize the mixing of the filler component and the isocyanate compound and the aggregation phenomenon between the filler particles in the filler component.

[0090] The curable composition according to another example of the present application includes a main agent part containing a polyol compound and a curing agent part. The curing agent part may be the curable composition according to an example of the present application described above or may contain the composition. Here, in order to distinguish the curable composition according to another example of the present application from the curable composition according to an example of the present application, the curable composition according to another example of the present application can be said to be a curable composition mixed with the main agent part. Since the curing agent part contains the curable composition according to an example of the present application described above, the specific content is omitted.

[0091] The curable composition mixed with the main agent part according to an example of the present application may contain components that can be converted into a resin through a curing reaction or a polymerization reaction, as well as components generally known as resins. It may have adhesion or tackiness performance by itself, or may have adhesion or tackiness performance through reactions such as a curing reaction.

[0092] On the other hand, the curable composition mixed with the main agent part according to an example of the present application may be a solvent-based curable composition, an aqueous curable composition or a solvent-free curable composition, and may also be an active energy ray (for example, ultraviolet ray) curable type, a moisture curable type, a heat curable type or a room temperature curable type. Considering the object of the present application, it is appropriate that the curable composition mixed with the main agent part is a solvent-free type and / or a room temperature curable type.

[0093] The term polyol compound used in this application means a compound having two or more hydroxyl groups at the ends of its chemical structure. More specifically, a compound having two hydroxyl groups is called a diol, and a compound having three hydroxyl groups is called a triol. The polyol compound contained in the main component part in the curable composition mixed with the main component part according to an example of this application is not particularly limited as long as it satisfies the above definition. For example, (poly)ethylene glycol, diethylene glycol, (poly)propylene glycol, 1,2-butylene glycol, 2,3-butylene glycol, 1,3-propanediol, 1,3-butanediol, 1,4-butanediol, 1,6-hexanediol, neopentyl glycol, 1,2-ethylhexyl diol, 1,5-pentanediol, 1,9-nonanediol, 1,10-decanediol, 1,3-cyclohexanedimethanol and 1,4-cyclohexanedimethanol, (poly)ethylene triol, diethylene triol, (poly)propylene triol, glycerin, 1,2,3-butanetriol, 1,2,4-butanetriol, 1,3,4-hexanetriol, 1,3,6-hexanetriol units and trimethylolpropane, etc. may be used. In still other examples, the polyol compound contained in the main component part may contain polyester polyol. The polyester polyol may contain carboxylic acid-based polyol and / or caprolactone-based polyol. Here, the carboxylic acid-based polyol may be a polyol compound represented by Chemical Formula 1 below, and the caprolactone-based polyol may be a polyol compound represented by Chemical Formula 2 below.

[0094]

Chemical Formula

[0095]

Chemical Formula

[0096] In Formulas 1 and 2, X is a unit derived from a dicarboxylic acid, Y is a unit derived from a polyol, such as a triol or a diol unit, and n and m are arbitrary numbers.

[0097] In the above, the unit derived from a dicarboxylic acid is a unit formed by the urethane reaction of the dicarboxylic acid with a polyol, and the unit derived from a polyol compound is a unit formed by the urethane reaction of the polyol with a dicarboxylic acid or caprolactone.

[0098] That is, when the hydroxy group of the polyol compound reacts with the carboxyl group of the dicarboxylic acid, a water (H 2 O) molecule is eliminated by a condensation reaction to form an ester bond. In Formula 1, X means the part excluding the ester bond part after the dicarboxylic acid forms an ester bond by the condensation reaction, and Y is also the part excluding the ester bond after the polyol compound forms an ester bond by the condensation reaction. The ester bond is represented by Formula 1.

[0099] Also, in Formula 2, Y also represents the part excluding the ester bond after the polyol compound forms an ester bond with caprolactone.

[0100] On the other hand, when the unit derived from the polyol compound of Y is a unit derived from a polyol containing three or more hydroxy groups such as a triol unit, a structure with a branch formed in the Y part may be embodied in the structure of the chemical formula.

[0101] In Chemical Formula 1, the type of the dicarboxylic acid-derived unit of X is not particularly limited, but in order to secure the desired physical properties, it may be any unit selected from the group consisting of phthalic acid unit, isophthalic acid unit, terephthalic acid unit, trimellitic acid unit, tetrahydrophthalic acid unit, hexahydrophthalic acid unit, tetrachlorophthalic acid unit, oxalic acid unit, adipic acid unit, azelaic acid unit, sebacic acid unit, succinic acid unit, malic acid unit, glutaric acid unit, malonic acid unit, pimelic acid unit, suberic acid unit, 2,2-dimethylsuccinic acid unit, 3,3-dimethylglutaric acid unit, 2,2-dimethylglutaric acid unit, maleic acid unit, fumaric acid unit, itaconic acid unit, and fatty acid unit.

[0102] In Chemical Formulas 1 and 2, the type of the polyol-derived unit of Y is not particularly limited, but it may be any one or two or more selected from the group consisting of ethylene glycol unit, propylene glycol unit, 1,2-butylene glycol unit, 2,3-butylene glycol unit, 1,3-propanediol unit, 1,3-butanediol unit, 1,4-butanediol unit, 1,6-hexanediol unit, neopentyl glycol unit, 1,2-ethylhexyl diol unit, 1,5-pentanediol unit, 1,10-decanediol unit, 1,3-cyclohexanedimethanol unit, 1,4-cyclohexanedimethanol unit, glycerin unit, and trimethylolpropane unit.

[0103] In Chemical Formula 1, n is an arbitrary number, and its range may be selected in consideration of the desired physical properties, for example, it may be about 2 to 10 or 2 to 5. In Chemical Formula 2, m is an arbitrary number, and its range may be selected in consideration of the desired physical properties, for example, it may be about 1 to 10 or 1 to 5.

[0104] In a curable composition mixed with the main agent part according to an example of the present application, for the main agent part, the lower limit of the weight ratio with respect to the total weight of the main agent part of the polyol compound may be about 1 wt%, 1.5 wt%, 2 wt%, 2.5 wt%, 3 wt%, 3.5 wt%, 4 wt%, 4.5 wt%, 5 wt%, 5.5 wt%, 6 wt%, 6.5 wt%, 7 wt%, 7.5 wt%, 8 wt%, 8.5 wt% or 9.5 wt%, and the upper limit may be about 20 wt%, 18 wt%, 16 wt%, 14 wt%, 12 wt% or 10 wt%. The above ratio is within the range that is equal to or greater than any of the above-mentioned lower limits or exceeds them, within the range that is equal to or less than any of the above-mentioned upper limits or is less than them, or within the range that is equal to or greater than any of the above-mentioned lower limits or exceeds them while being equal to or less than any of the above-mentioned upper limits or less than them. When adjusting the polyol compound in the above content ratio, it is possible to ensure a cured product having excellent surface hardness when combined with the curing agent part.

[0105] In a curable composition mixed with the main agent part according to an example of the present application, the main agent part may further contain a filler component as required in the process. The filler component may be a thermally conductive filler, and one or more appropriately selected types may be used as required. The form and ratio are not particularly limited, and they may be selected in consideration of the viscosity of the main agent part, the possibility of sedimentation in the cured product after combination with the curing agent part, the desired thermal resistance or thermal conductivity, insulation, filling effect or dispersibility, etc. Also, the same type of filler may be used, or those with different shapes may be mixed and used, or those with different average particle sizes may be mixed and used. For example, aluminum hydroxide, aluminum and alumina may be mixed and used, and their respective shapes and average particle sizes may be different from each other.

[0106] In the curable composition mixed with the main agent part according to an example of the present application, the filler component of the main agent part may be, for example, an oxide filler such as aluminum oxide (alumina), magnesium oxide, beryllium oxide or titanium oxide, a nitride filler such as boron nitride, silicon nitride or aluminum nitride, a carbide filler such as silicon carbide, a hydroxide filler such as aluminum hydroxide or magnesium hydroxide, a metal filler such as copper, silver, iron, aluminum or nickel, a metal alloy filler such as titanium, a silicon powder such as quartz, glass or silica, or a carbon filler such as graphite or activated carbon, etc., and is not limited thereto.

[0107] In the curable composition mixed with the main agent part according to an example of the present application, the lower limit of the weight ratio of the main agent part to 100 parts by weight of the polyol compound of the filler component may be about 500 parts by weight, 600 parts by weight, 700 parts by weight, 800 parts by weight or 900 parts by weight, and the upper limit thereof may be about 2,000 parts by weight, 1,500 parts by weight or 1,000 parts by weight. The above ratio is within the range that is equal to or more than any of the lower limits described above or exceeds the lower limit, within the range that is equal to or less than any of the upper limits described above or is less than the upper limit, or within the range that is equal to or more than any of the lower limits described above or exceeds the lower limit while being equal to or less than any of the upper limits described above or is less than the upper limit. When adjusting the contents of the polyol compound and the filler component in the above ratio, a cured product having excellent surface hardness and thermal conductivity can be ensured when combined with the curing agent part.

[0108] In the curable composition mixed with the main agent part according to an example of the present application, the filler component of the main agent part may contain at least one selected from the group consisting of a first filler, a second filler and a third filler. The average particle sizes of the first to third fillers are different from each other.

[0109] The lower limit of the average particle size of the first filler component may be about 60 μm, 61 μm, 62 μm, 63 μm, 64 μm, 65 μm, 66 μm, 67 μm, 68 μm, 69 μm or 70 μm, and the upper limit thereof may be about 200 μm, 190 μm, 180 μm, 170 μm, 160 μm or 150 μm. The average particle size is within a range that is equal to or greater than any one of the aforementioned lower limits or exceeds them, within a range that is equal to or less than any one of the aforementioned upper limits or is less than them, or within a range that is equal to or greater than any one of the aforementioned lower limits or exceeds them while being equal to or less than any one of the aforementioned upper limits or less than them.

[0110] The lower limit of the average particle size of the second filler may be about 10 μm, 12 μm, 14 μm, 16 μm, 18 μm or 20 μm, and the upper limit thereof may be about 58 μm, 56 μm, 54 μm, 52 μm, 50 μm, 48 μm, 46 μm, 44 μm, 42 μm or 40 μm. The average particle size is within a range that is equal to or greater than any one of the aforementioned lower limits or exceeds them, within a range that is equal to or less than any one of the aforementioned upper limits or is less than them, or within a range that is equal to or greater than any one of the aforementioned lower limits or exceeds them while being equal to or less than any one of the aforementioned upper limits or less than them.

[0111] The upper limit of the average particle size of the third filler may be about 10 μm, 9 μm, 8 μm, 7 μm, 6 μm, 5 μm, 4 μm, 3 μm or 2 μm, and the upper limit thereof may be about 0.01 μm, 0.05 μm, 0.1 μm or 0.5 μm. The average particle size is within a range that is equal to or greater than any one of the aforementioned lower limits or exceeds them, within a range that is equal to or less than any one of the aforementioned upper limits or is less than them, or within a range that is equal to or greater than any one of the aforementioned lower limits or exceeds them while being equal to or less than any one of the aforementioned upper limits or less than them.

[0112] The first filler may be a hydroxide filler. Also, the second filler and the third filler may each independently be at least one filler selected from the group consisting of an oxide filler, a nitride filler, a carbide filler, a metal filler, an alloy filler, silicon powder, and a carbon filler. By selecting the first filler component, the second filler component, and the third filler component from the listed types and adjusting the ratio of the average particle size and / or the weight ratio, appropriate thixotropic properties and viscosity can be ensured in the process. After being mixed with the hardener part, a cured product with excellent thermal conductivity can be formed.

[0113] In the curable composition mixed with the main agent part according to an example of the present application, when the filler component of the main agent part simultaneously contains the first filler component and the second filler component, the lower limit of the average particle size ratio (DMF1 / DMF2) of the first filler component (DMF1) and the second filler component (DMF2) may be about 1, 1.2, 1.4, 1.6, 1.8, 2, 2.2, 2.4, 2.6, 2.8, 3, 3.2, or 3.4, and the upper limit may be about 5, 4.8, 4.6, 4.4, 4.2, 4, 3.8, or 3.6. The ratio is within the range that is equal to or greater than any of the lower limits described above or exceeds them, within the range that is equal to or less than any of the upper limits described above or is less than them, or within the range that is equal to or greater than any of the lower limits described above or exceeds them while being equal to or less than any of the upper limits described above or is less than them. By satisfying the ratio, appropriate thixotropic properties and viscosity can be ensured in the process.

[0114] In addition, in the curable composition mixed with the main agent part according to an example of the present application, when the filler component of the main agent part simultaneously contains the first filler component and the second filler component, the lower limit of the weight ratio (MF1 / MF2) of the first filler component (MF1) to the second filler component (MF2) may be about 0.1, 0.2, 0.3, 0.4, 0.5, 0.6 or 0.7, and the upper limit thereof may be about 5, 4.5, 4, 3.5, 3, 2.5, 2, 1.5, 1 or 0.75. The ratio is within the range that is equal to or greater than any of the lower limits described above, within the range that is equal to or less than any of the upper limits described above, or within the range that is equal to or greater than any of the lower limits described above while being equal to or less than any of the upper limits described above.

[0115] By satisfying the above ratio, appropriate thixotropy and viscosity can be ensured in the process.

[0116] In addition, in the curable composition mixed with the main agent part according to an example of the present application, when the filler component of the main agent part simultaneously contains the first filler component and the third filler component, the lower limit of the average particle size ratio (DMF1 / DMF3) of the first filler component (DMF1) to the third filler component (DMF3) may be about 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29 or 30, and the upper limit thereof may be about 50, 49, 48, 47, 46, 45, 44, 43, 42, 41, 40, 39, 38, 37, 36 or 35. The ratio is within the range that is equal to or greater than any of the lower limits described above, within the range that is equal to or less than any of the upper limits described above, or within the range that is equal to or greater than any of the lower limits described above while being equal to or less than any of the upper limits described above. By satisfying the above ratio, appropriate thixotropy and viscosity can be ensured in the process.

[0117] In a curable composition mixed with a main agent part according to an example of the present application, when the filler component of the main agent part simultaneously contains a first filler component and a third filler component, the lower limit of the weight ratio (MF1 / MF3) of the first filler component (MF1) to the third filler component (MF3) may be about 0.5, 0.6, 0.7, 0.8, 0.9, or 1, and the upper limit thereof may be about 10, 8, 6, 4, or 2. The ratio is within a range that is equal to or greater than any of the lower limits described above, within a range that is equal to or less than any of the upper limits described above, or within a range that is equal to or greater than any of the lower limits described above while being equal to or less than any of the upper limits described above. By satisfying the ratio, appropriate thixotropy and viscosity can be ensured in the process.

[0118] In a curable composition mixed with a main agent part according to an example of the present application, the main agent part may further contain an additive, and the additive may contain at least one selected from the group consisting of a curing retarder, a catalyst, a plasticizer, a flame retardant, a thixotropy imparting agent, a diluent, a surface treatment agent, a coupling agent, a dispersant, and the like. If the curing retarder can delay the curing of the main agent part, it may be used without limitation in the art. For example, 1-dodecyl mercaptan or the like may be used. Further, if the catalyst can promote the curing reaction when combined with the main agent part and the curing agent part, it may be used without limitation in the art. For example, dibutyltin dilaurate may be used.

[0119] The curable composition mixed with the main agent part according to an example of the present application may be used by mixing the main agent part and the curing agent part in an appropriate volume ratio. The volume ratio means the ratio (B / A) of the volume (B) of the curing agent part to the volume (A) of the main agent part. For example, the lower limit of the ratio B / A may be about 0.01, 0.05, 0.1, 0.5, 1, 10, 50, or 100, and the upper limit thereof may be about 200, 150, 100, 50, 40, 30, 20, 10, 9, 8, 7, 6, 5, 4, 3, 2, 1, 0.5, 0.1, 0.05, or 0.01. The ratio is within a range that is equal to or greater than any of the lower limits described above or exceeds them, within a range that is equal to or less than any of the upper limits described above or is less than them, or within a range that is equal to or greater than any of the lower limits described above or exceeds them while being equal to or less than any of the upper limits described above or is less than them.

[0120] The curable composition mixed with the main agent part according to an example of the present application can be cured to form a cured product, and may have at least one of the following physical properties. Each of the following physical properties is independent, and none of the physical properties takes precedence over the others. The cured product can satisfy at least one or two or more of the following physical properties. The cured product of the curable composition mixed with the main agent part according to an example of the present application that satisfies at least one or two or more of the following physical properties is due to the combination of each component.

[0121] The lower limit of the thermal conductivity of the cured product of the curable composition mixed with the main agent part according to an example of the present application may be about 3.0, 3.05 or 3.1, and the upper limit thereof may be about 20 W / m·K, 18 W / m·K, 16 W / m·K, 14 W / m·K, 12 W / m·K, 10 W / m·K, 8 W / m·K, 6 W / m·K or 4 W / m·K. The thermal conductivity is within a range that is equal to or greater than any of the lower limits described above, or while being equal to or greater than any of the lower limits described above, it is within a range that is less than or equal to any of the upper limits described above. Such thermal conductivity may be measured in accordance with ASTM D5470 standard or ISO 22007-2 standard along the thickness direction of the sample (cured product) with a thickness of 20 mm in the state where the cured product is produced.

[0122] The lower limit of the surface hardness of the cured product of the curable composition mixed with the main agent part according to an example of the present application may be about 50, 55, 60, 65, 70, 75 or 80 in Shore A hardness, and the upper limit thereof may be about 80, 75, 70, 65, 60 or 55 in Shore D hardness, or may be about 100, 95 or 90 in Shore A hardness. The hardness is within a range that is equal to or greater than any of the lower limits described above, or while being equal to or greater than any of the lower limits described above, it is within a range that is less than or equal to any of the upper limits described above. Such hardness may be measured in accordance with ASTM D2240 standard, and the specific method is summarized in the examples of this specification.

[0123] The cured product of the curable composition mixed with the main agent part according to an example of the present application can ensure durability for application to products that require a long warranty period such as automobiles (in the case of automobiles, about 15 years or more). Durability means that after maintaining at a low temperature of about -40°C for 30 minutes and then raising the temperature to 80°C again and maintaining for 30 minutes as one cycle, the module case or battery cell of the battery module does not separate, peel, or crack after 100 repetitions of the above cycle in a thermal shock test.

[0124] The cured product of the curable composition mixed with the main agent part according to an example of the present application may have an electrical insulation of 10 kV / mm or more, 15 kV / mm or more, or 20 kV / mm or more. The higher the breakdown voltage value, the better the cured product of the curable composition mixed with the main agent part according to an example of the present application exhibits excellent insulation, and it may be 50 kV / mm or less, 45 kV / mm or less, 40 kV / mm or less, 35 kV / mm or less, 30 kV / mm or less, but it is not particularly limited. To achieve the above breakdown voltage, an insulating filler may be applied to the curable composition mixed with the main agent part according to an example of the present application. Generally, among thermal conductive fillers, ceramic fillers are known as components that can ensure insulation. The electrical insulation may be measured by the breakdown voltage measured according to ASTM D149 standard. Also, if the cured product of the curable composition mixed with the main agent part according to an example of the present application can ensure the above electrical insulation, stability can be ensured while maintaining performance for various materials, such as the case or battery cell included in the battery module.

[0125] The cured product of the curable composition mixed with the main agent part according to an example of the present application has a volume resistivity of 1×10 10 Ω·cm or more, 3×10 10 Ω·cm or more, 7×10 10 Ω·cm or more, or 9×10 10 Ω·cm or more. In other examples, the cured product of the curable composition mixed with the main agent part according to an example of the present application has a volume resistivity of 1×1014 less than Ω·cm, 7.5×10 13 less than Ω·cm, 5×10 13 less than Ω·cm, 2.5×10 13 less than Ω·cm or 1×10 13 It may also be less than Ω·cm. Here, the volume resistivity of the cured product of the curable composition mixed with the main component part according to an example of the present application may be within a range formed by appropriately selecting the above-listed upper and lower limits. The volume resistivity may be measured with a volume resistivity measuring device using a cured product of the curable composition mixed with the main component part according to an example of the present application having a thickness of 0.2 cm in accordance with the ASTM D257 standard. If the volume resistivity of the cured product of the curable composition mixed with the main component part according to an example of the present application as described above can be ensured, excellent electrical insulation performance can be ensured. Therefore, it can be used in various materials, for example, cases or battery cells included in battery modules, etc., to maintain performance and ensure stability.

[0126] The cured product of the curable composition mixed with the main component part according to an example of the present application may have a specific gravity of 5 or less. In other examples, the specific gravity may be 4.5 or less, 4 or less, 3.5 or less, or 3 or less. Since the lower the numerical value of the specific gravity of the cured product of the curable composition mixed with the main component part according to an example of the present application, the more advantageous it is for weight reduction of the applied product, the lower limit is not particularly limited. For example, the specific gravity may be about 1 or more, or 1.2 or more.

[0127] The cured product of the curable composition mixed with the main agent part according to an example of the present application is preferably free of volatile substances as much as possible. For example, the cured product of the curable composition mixed with the main agent part according to an example of the present application may have a proportion of non-volatile components of 90% by weight or more, 95% by weight or more, or 98% by weight or more. The proportion with the non-volatile component can be defined in the following manner. That is, the non-volatile content can be defined as the portion remaining after maintaining the cured product of the curable composition mixed with the main agent part according to an example of the present application at 100 °C for about 1 hour. Therefore, the proportion can be measured based on the initial weight of the cured product of the curable composition mixed with the main agent part according to an example of the present application and the proportion after maintaining at 100 °C for about 1 hour.

[0128] The cured product of the curable composition mixed with the main agent part according to an example of the present application may, if necessary, have excellent resistance to deterioration and may be required to have stability that does not chemically react as much as possible.

[0129] The cured product of the curable composition mixed with the main agent part according to an example of the present application may advantageously have a low shrinkage rate during or after the curing process. Thereby, it is possible to prevent the occurrence of peeling or voids that may occur during the manufacturing or use process of various materials, such as cases or battery cells included in a battery module. The shrinkage rate may be appropriately adjusted within a range capable of showing the above-described effects. For example, it may be less than 5%, less than 3%, or about less than 1%. Since the lower the numerical value of the shrinkage rate, the more advantageous it is, the lower limit thereof is not particularly limited.

[0130] The cured product of the curable composition mixed with the main agent part according to an example of the present application may advantageously have a lower coefficient of thermal expansion (CTE). Thereby, it is possible to prevent peeling, generation of voids, etc. that may occur during the manufacturing or use process of various materials, such as the case or battery cells included in the battery module. The coefficient of thermal expansion may be appropriately adjusted within a range showing the above-described effects, and may be, for example, less than 300 ppm / K, less than 250 ppm / K, less than 200 ppm / K, less than 150 ppm / K, or less than 100 ppm / K. Since the lower the value of the coefficient of thermal expansion, the more advantageous it is, the lower limit thereof is not particularly limited.

[0131] The cured product of the curable composition mixed with the main agent part according to an example of the present application may have its tensile strength appropriately adjusted, whereby excellent impact resistance, etc. can be ensured. The tensile strength may be adjusted, for example, within a range of about 1.0 MPa or more.

[0132] The cured product of the curable composition mixed with the main agent part according to an example of the present application may further have a 5% weight loss temperature in thermogravimetric analysis (TGA) of 400 °C or higher, or an 800 °C residue of 70% by weight or higher. Due to such characteristics, the high-temperature stability can be further improved for various materials, such as the cases or battery cells included in battery modules. In other examples, the 800 °C residue may be about 75% by weight or higher, about 80% by weight or higher, about 85% by weight or higher, or about 90% by weight or higher. In other examples, the 800 °C residue may be about 99% by weight or less. The thermogravimetric analysis (TGA) may be measured in the range of 25 °C to 800 °C at a heating rate of 20 °C / min under a nitrogen (N2) atmosphere of 60 cm3 / min. The results of the thermogravimetric analysis (TGA) can also be achieved through the adjustment of the composition of the cured product of the curable composition mixed with the main agent part according to an example of the present application. For example, the 800 °C residue depends on the type or proportion of the thermally conductive filler contained in the cured product of the curable composition mixed with the main agent part according to an example of the present application. When an excessive amount of the thermally conductive filler is included, the residue increases. However, when the polymer and / or monomer used in the curable composition mixed with the main agent part according to an example of the present application has generally higher heat resistance than other polymers and / or monomers, the residue is even higher. Thus, the polymer and / or monomer components contained in the cured product of the curable composition mixed with the main agent part according to an example of the present application also affect its hardness.

[0133] The curable composition mixed with the main agent part according to an example of the present application may be formed by mixing each of the above-listed components. Also, for the curable composition mixed with the main agent part according to an example of the present application, as long as all the necessary components are included, the mixing order is not particularly limited.

[0134] The curable composition mixed with the main agent part according to an example of the present application can dissipate the heat generated when used in various electrical and electronic products such as irons, washing machines, dryers, clothing management machines, electric shavers, microwave ovens, electric ovens, electric rice cookers, refrigerators, dishwashers, air conditioners, fans, humidifiers, air purifiers, mobile phones, radios, TVs, radios, computers, laptops, etc., or batteries such as secondary batteries. In particular, in a battery-powered vehicle battery manufactured by gathering battery cells to form one battery module and gathering a plurality of battery modules to form one battery pack, the curable composition may be used as a material for connecting the battery cells or battery modules. When the curable composition is used as a material for connecting the battery cells or battery modules, it can dissipate the heat generated from the battery cells and play a role in fixing the battery cells from external impacts and vibrations.

[0135] The cured product of the curable composition mixed with the main agent part according to an example of the present application can transfer the heat generated from a heating element (for example, a heat-generating element) to a cooling part. That is, the cured product of the curable composition mixed with the main agent part according to an example of the present application can dissipate the heat generated from the heating element. Here, the heating element may be a battery cell or a battery module.

[0136] The cured product of the curable composition mixed with the main agent part according to an example of the present application is located between the heating element and the cooling part and can bring them into thermal contact. Thermal contact means that the cured product of the curable composition mixed with the main agent part according to an example of the present application physically directly contacts the heating element and the cooling part to dissipate the heat generated from the heating element to the cooling part, or even if the cured product of the curable composition mixed with the main agent part according to an example of the present application does not directly contact the heating element and / or the cooling part (that is, there is a separate layer between the cured product of the curable composition mixed with the main agent part according to an example of the present application and the heating element and / or the cooling part), it means dissipating the heat generated from the heating element to the cooling part.

Advantages of the Invention

[0137] This application can provide a curable composition that exhibits a low density and is advantageous for weight reduction, has suppressed viscosity change over time, and has excellent storage stability and shelf stability, as well as its uses. Further, the curable composition exhibits excellent compatibility during the manufacturing process and, when cured, can form a cured product having high thermal conductivity, low specific gravity (density), and relatively high hardness. This application can further provide an apparatus including the curable composition or its cured product.

Modes for Carrying Out the Invention

[0138] Hereinafter, the present invention will be described through examples and comparative examples, but the scope of the present invention is not limited by the following content.

[0139] 1. Viscosity Measurement The viscosity of the curable composition was measured using a viscometer (manufacturer: Brookfield, model name: DV3T Rheometer) and a spindle CPA-52Z. The spindle was rotated at a shear rate of about 1.2 rpm at room temperature (about 25°C) for about 180 seconds, and the finally measured value was taken as the measured viscosity.

[0140] A plate was attached to the plate connection part of the viscometer, and the distance between the spindle and the plate was adjusted via an adjustment lever. After separating the plate, about 0.5 mL of a sample (curable composition) was applied to the center of the plate, and then the plate was attached again to the plate connection part of the viscometer. After waiting until the torque became 0, the spindle was rotated at a shear rate of 1.2 rpm at room temperature (about 25°C) for 180 seconds, and finally the measured viscosity was confirmed.

[0141] 2. Measurement of Viscosity Change Rate The initial viscosity V of the curable composition i was measured by the above viscosity measurement method. The initial viscosity V iis the viscosity measured within about 10 minutes from the time when the curable composition was produced. Initial viscosity V i After maintaining the curable composition for which the viscosity V f was measured at room temperature (about 25°C) for about 240 hours, the viscosity V

[0142] Next, the viscosity change rate V i and V f were substituted into the following general formula 1 to obtain the viscosity change rate V R . The viscosity measurement was performed on the curable composition for which the compatibility was evaluated as PASS in the following compatibility evaluation method.

[0143] [Equation 1] V R = 100×|V f - V i | / V i (General formula 1)

[0144] In general formula 1, V i is the initial viscosity, and V f is the viscosity measured after maintaining the curable composition for which the initial viscosity V i was measured at room temperature (about 25°C) for 240 hours.

[0145] 3. Density measurement The curable composition was filled into a 10 mL vial using a pneumatic dispenser. The weight (W 1 , unit: g) of the vial containing the curable composition at room temperature (about 25°C) was measured, and the weight of the empty vial (W 2 , unit: g) before being filled with the curable composition was also measured as the weight of the vial measured at room temperature (about 25°C). The weight W 1 (g) minus the weight W 2 (g) was divided by 10 mL to obtain the density (W 3 / 10, unit: g / mL). 3 / 10, unit: g / mL) was determined.

[0146] 4. Compatibility evaluation The compatibility of the curable composition was evaluated according to the following criteria.

[0147] <Compatibility evaluation criteria> PASS: When the produced curable composition is visually observed, if a state with a soft surface without filler aggregation is confirmed NG: When the produced curable composition is visually observed, if a state with a rough surface due to filler aggregation is confirmed

[0148] 5. Shore A hardness measurement The curable composition produced in the example or comparative example was mixed with the main agent part of Production Example 1 at a volume ratio of 1:1, and the resulting curable composition was injected into a disk-shaped silicone mold with a diameter of 50 mm and a thickness of 20 mm, and maintained at room temperature (about 25°C) for about 24 hours to produce a cured product. Using a hardness tester (Shore A durometer), the Shore A hardness of the surface of the cured product was measured at room temperature (about 25°C) according to ASTM D2240 standard. After piercing the surface of the cured product in a flat state with an indenter capable of measuring the Shore A hardness of the hardness tester (manufacturer: TQC Sheen, product name: LD0550), the hardness was measured while maintaining the piercing force.

[0149] 6. Thermal conductivity measurement The thermal conductivity was measured using the Hot disk method. The curable composition produced in the example or comparative example was mixed with the main agent part of Production Example 1 at a volume ratio of 1:1, and the resulting curable composition was injected into a disk-shaped silicone mold with a diameter of 50 mm and a thickness of 20 mm, and maintained at room temperature (about 25°C) for about 24 hours to produce a cured product. Using a thermal conductivity measuring device (manufacturer: Hot disk, product name: TPS-2200), the thermal conductivity was measured along the thickness direction of the cured product according to ISO 22007-2 standard.

[0150] 7. Average particle size measurement The average particle size of the filler referred to in this specification is the D50 particle size, also known as the so-called median particle size, which is the particle size at the cumulative 50% of the volume-based cumulative curve of the particle size distribution. Such a particle size can be defined as the particle size at the point where the cumulative value becomes 50% in the cumulative curve with the total volume being 100% when obtaining the particle size distribution based on volume. The D50 particle size can be measured using the MASTERSIZER 3000 equipment of Marven in accordance with ISO-13320, and Ethanol is used as the solvent.

[0151] 8. Measurement of Filler Shape The sphericity of the filler can be defined as the ratio (S’ / S) of the surface area (S) of the particle and the surface area (S’) of the sphere having the same volume as the particle. For actual particles, generally circularity is used. The circularity is obtained by obtaining a two-dimensional image of the actual particle and representing it as the ratio of the boundary of the circle having the same area (A) as the image and the boundary of the image, and is obtained by the following mathematical formula.

[0152] <Circularity Mathematical Formula> Circularity = 4πA / P 2

[0153] The circularity is represented by a value from 0 to 1. A perfect circle has a value of 1, and the more irregular the shape of the particle, the lower the value is from 1. The sphericity value in this specification is the average value of the circularity measured by the particle analysis equipment (FPIA-3000) of Marven.

[0154] When the circularity measured as described above is 0.9 or more, it is defined as a spherical filler, and when it is less than 0.9, it is defined as a non-spherical or angular filler.

[0155] Production Example 1. Main Agent Part A polyol compound (P), a catalyst (C), alumina (FP1) (angular, average particle size: 1 μm to 2 μm), and an additive (AP) were mixed at a weight ratio of approximately 30:0.225:81.9:4.581 (P:C:FP1:AP) to produce a primary mixture (Mx1), and the primary mixture was stirred with a paste mixer at 500 rpm in the revolution direction and 400 rpm in the rotation direction until appropriate mixing was performed. Alumina (FP2) (spherical, average particle size: 20 μm) was added to the primary mixture at a ratio of 109.2 parts by weight with respect to 81.9 parts by weight of the alumina (FP1), and aluminum hydroxide (FP3) (angular, average particle size: 70 μm) was added to the container at a ratio of 81.9 parts by weight with respect to 81.9 parts by weight of the alumina (FP1) to produce a secondary mixture (Mx2). The secondary mixture (Mx2) was stirred with a paste mixer until it was uniformly mixed at 500 rpm in the revolution direction and 400 rpm in the rotation direction, and defoamed at 500 rpm in the revolution direction and 150 rpm in the rotation direction to produce a main agent part.

[0156] The weight ratio of the polyol compound (P), the catalyst (C), the alumina (FP1), the alumina (FP2), the aluminum hydroxide (FP3), and the additive (AP) in the main agent part was approximately 30:0.225:81.9:109.2:81.9:4.581 (P:C:FP1:FP2:FP3:AP).

[0157] As the polyol compound (P) in the main agent part, a caprolactone-based polyol (weight average molecular weight: about 860 g / mol) obtained by reacting 1,4-butanediol (1,4-butanediol, 1,4-BDol) and caprolactone (Caprolactone, CL) at a weight ratio of 1:2.78 (1,4-BDol:CL) was used. As the catalyst (C), dibutyltin dilaurate was used. As the additive (AP), a mixture of a curing retarder (AP1), a dispersant (AP2), and a flame retardant (AP3) at a weight ratio of 0.381:0.351:3.750 (AP1:AP2:AP3) was used. 1-Dodecyl mercaptan was used as the curing retarder, a phosphate-modified polyester dispersant was used as the dispersant, and a mixture of a phosphorus-based liquid flame retardant (J1) and a phosphorus-based solid flame retardant (J2) at a weight ratio of 1:1.5 (J1:J2) was used as the flame retardant.

[0158] Example 1. (1) Production of the curable composition (1) An isocyanate compound (I), aluminum hydroxide (FI1) (angular, average particle size: 1 μm to 2 μm), a plasticizer (Pz), and an additive (AI) were placed in a container at a weight ratio of 30:54.6:1.5:6.852 (I:FI1:Pz:AI) to produce a primary mixture (My1), and the primary mixture was stirred with a paste mixer at 500 rpm in the revolution direction and 400 rpm in the rotation direction until uniformly mixed. Aluminum hydroxide (FI2) (angular, average particle size: 70 μm) was placed in the container at a ratio of 109.2 parts by weight with respect to 54.6 parts by weight of the aluminum hydroxide (FI1), and spherical alumina (FI3) (spherical, average particle size: 20 μm) was placed in the container at a ratio of 109.2 parts by weight with respect to 54.6 parts by weight of the aluminum hydroxide (FI1), and then further mixed with the primary mixture (My1) to produce a secondary mixture (My2). The secondary mixture (My2) was stirred with a paste mixer at 500 rpm in the revolution direction and 400 rpm in the rotation direction until uniformly mixed, and then degassed at 500 rpm in the revolution direction and 150 rpm in the rotation direction to produce a curable composition.

[0159] The curable composition contained an isocyanate compound (I), aluminum hydroxide (FI1), aluminum hydroxide (FI2), spherical alumina (FI3), a plasticizer (Pz), and an additive (AI) at a weight ratio of 30:54.6:109.2:109.2:1.5:6.852 (I:FI1:FI2:FI3:Pz:AI).

[0160] As the isocyanate compound (I), a mixture of hexamethylene diisocyanate trimer and hexamethylene diisocyanate at a weight ratio of about 1:1 was used. As the plasticizer, diisononyl phthalate (DINA) was used. As the additive (AI), a mixture of a moisture absorbent (AI1), a dispersant (AI2), and a flame retardant (AI3) at a weight ratio of 2.430:0.672:3.750 (AI1:AI2:AI3) was used. As the moisture absorbent, a vinyl group-containing siloxane compound was used. As the dispersant, a phosphate-modified polyester dispersant was used. As the flame retardant, a mixture of a phosphorus-based liquid flame retardant (J1) and a phosphorus-based solid-phase flame retardant (J2) at a weight ratio of 1:1.5 (J1:J2) was used.

[0161] (2) Production of the curable composition (2) The main agent part (MP) of Production Example 1 and the curable composition (1) (hardening agent part (HP)) were each placed in a 40 mL cartridge, and after fastening a static mixer, using a pneumatic dispenser, they were mixed while discharging at a volume ratio of 1:1 (MP:HP) to produce the curable composition (2).

[0162] Example 2. (1) Production of the curable composition (1) An isocyanate compound (I), angular aluminum hydroxide (FI1) (angular, average particle size: about 1 μm to 2 μm), a plasticizer (Pz), and an additive (AI) were placed in a container at a weight ratio of 30:54.6:3.0:6.852 (I:FI1:Pz:AI) to produce a primary mixture (My1), and the primary mixture was stirred with a paste mixer at 500 rpm in the idling direction and 400 rpm in the rotating direction until uniformly mixed. Aluminum hydroxide (FI2) (angular, average particle size: about 70 μm) was placed in the container at a ratio of 109.2 parts by weight with respect to 54.6 parts by weight of the aluminum hydroxide (FI1), and alumina (FI3) (spherical, average particle size: about 20 μm) was placed in the container at a ratio of 109.2 parts by weight with respect to 54.6 parts by weight of the aluminum hydroxide (FI1), and then mixed with the primary mixture (My1) to produce a secondary mixture (My2). The secondary mixture (My2) was stirred with a paste mixer until properly mixed at 500 rpm in the revolution direction and 400 rpm in the rotation direction, and further defoamed at 500 rpm in the revolution direction and 150 rpm in the rotation direction to produce a curable composition (1).

[0163] The curable composition (1) contained an isocyanate compound (I), aluminum hydroxide (FI1), aluminum hydroxide (FI2), alumina (FI3), a plasticizer (Pz), and an additive (AI) at a weight ratio of 30:54.6:109.2:109.2:3.0:6.852 (I:FI1:FI2:FI3:Pz:AI).

[0164] As the isocyanate compound (I), the plasticizer (Pz), and the additive (AI), the same ones as in Example 1 were used.

[0165] (2) Production of curable composition (2) The curable composition (1) was mixed with the main agent part in the same manner as in Example 1 to produce a curable composition (2).

[0166] Comparative Example 1. (1) Production of curable composition (1) An isocyanate compound (I), alumina (FI4) (angular, average particle size: about 1 μm to 2 μm), and an additive (AI) were placed in a container at a weight ratio of 30:54.6:6.852 (I:FI1:AI) to produce a primary mixture (My1), and the primary mixture was stirred first with a paste mixer at 500 rpm in the revolution direction and 400 rpm in the rotation direction until properly mixed. Alumina (FI3) (spherical, average particle size: about 20 μm) was placed in the container at a ratio of 109.2 parts by weight with respect to 54.6 parts by weight of the alumina (FI4), and alumina (FI5) (spherical, average particle size: about 70 μm) was placed in the container at a ratio of 109.2 parts by weight with respect to 54.6 parts by weight of the alumina (FI4), and further mixed with the stirred primary mixture (My1) to produce a secondary mixture (My2). The secondary mixture (My2) was stirred with a paste mixer at 500 rpm in the revolution direction and 400 rpm in the rotation direction until properly mixed, and then degassed at 500 rpm in the revolution direction and 150 rpm in the rotation direction to produce a curable composition (2).

[0167] The curable composition contained an isocyanate compound (I), alumina (FI4), alumina (FI3), alumina (FI5), and an additive (AI) at a weight ratio of 30:54.6:109.2:109.2:6.852 (I:FI4:FI3:FI5:AI). In the above, the isocyanate compound (I) and the additive (AI) were the same as those in Example 1.

[0168] (2) Production of curable composition (2) The curable composition (1) was mixed with the main agent part in the same manner as in Example 1 to produce a curable composition (2).

[0169] Comparative Example 2. (1) Production of curable composition (1) An isocyanate compound (I), aluminum hydroxide (FI1) (angular, average particle size: about 1 μm to 2 μm), and an additive (AI) were placed in a container at a weight ratio of 30:54.6:6.852 (I:FI1:AI) to produce a primary mixture (My1), which was first stirred with a paste mixer at 500 rpm in the revolution direction and 400 rpm in the rotation direction until properly mixed. Angular aluminum hydroxide (FI2) (angular, average particle size: about 70 μm) was placed in the container at a ratio of 13.65 parts by weight with respect to 54.6 parts by weight of the aluminum hydroxide (FI1), alumina (FI3) (spherical, average particle size: about 20 μm) was placed in the container at a ratio of 109.2 parts by weight with respect to 54.6 parts by weight of the aluminum hydroxide (FI1), alumina (FI5) (spherical, average particle size: about 70 μm) was placed in the container at a ratio of 95.55 parts by weight with respect to 54.6 parts by weight of the aluminum hydroxide (FI1), and the stirred primary mixture (My1) was further mixed to produce a secondary mixture (My2). The secondary mixture (My2) was stirred with a paste mixer at 500 rpm in the revolution direction and 400 rpm in the rotation direction until properly mixed, and then degassed at 500 rpm in the revolution direction and 150 rpm in the rotation direction to produce a curable composition (1).

[0170] The curable composition (1) contained an isocyanate compound (I), aluminum hydroxide (FI1), aluminum hydroxide (FI2), alumina (FI3), alumina (FI5), and an additive (AI) at a weight ratio of 30:54.6:13.65:109.2:95.55:6.852 (I:FI1:FI2:FI3:FI5:AI). The isocyanate compound (I) and the additive (AI) used were the same as those in Example 1.

[0171] (2) Production of curable composition (2) The curable composition (1) was mixed with the main agent part in the same manner as in Example 1 to produce a curable composition (2).

[0172] Comparative Example 3. (1) Production of curable composition (1) An isocyanate compound (I), aluminum hydroxide (FI1) (angular, average particle size: about 1 μm to 2 μm), and an additive (AI) were placed in a container at a weight ratio of 30:54.6:6.852 (I:FI1:AI) to produce a primary mixture (My1), which was then stirred first with a paste mixer at 500 rpm in the revolution direction and 400 rpm in the rotation direction until properly mixed. Aluminum hydroxide (FI2) (angular, average particle size: about 70 μm) was placed in the container at a ratio of 68.25 parts by weight with respect to 54.6 parts by weight of the aluminum hydroxide (FI1), alumina (FI3) (spherical, average particle size: about 20 μm) was placed in the container at a ratio of 109.2 parts by weight with respect to 54.6 parts by weight of the aluminum hydroxide (FI1), spherical alumina (FI5) (spherical, average particle size: about 70 μm) was placed in the container at a ratio of 40.95 parts by weight with respect to 54.6 parts by weight of the aluminum hydroxide (FI1), and a secondary mixture (My2) was produced by further mixing with the primary mixture (My1). The secondary mixture (My2) was stirred with a paste mixer at 500 rpm in the revolution direction and 400 rpm in the rotation direction until properly mixed, and then underwent a defoaming process at 500 rpm in the revolution direction and 150 rpm in the rotation direction to finally produce a curable composition (1).

[0173] The curable composition (1) contained the isocyanate compound (I), aluminum hydroxide (FI1), aluminum hydroxide (FI2), alumina (FI3), alumina (FI5), and additive (AI) at a weight ratio of 30:54.6:68.25:109.2:40.95:6.852 (I:FI1:FI2:FI3:FI5:AI). The isocyanate compound (I) and additive (AI) used were the same as those in Example 1 above.

[0174] (2) Production of curable composition (2) The curable composition (1) was mixed with the main agent part in the same manner as in Example 1 to produce a curable composition (2).

[0175] Comparative Example 4. (1) Production of curable composition An isocyanate compound (I), aluminum hydroxide (FI1) (angular, average particle size: about 1 μm to 2 μm), and an additive (AI) were placed in a container at a weight ratio of 30:54.6:6.852 (I:FI1:AI) to produce a primary mixture (My1), which was initially stirred with a paste mixer at 500 rpm in the revolution direction and 400 rpm in the rotation direction until properly mixed. Aluminum hydroxide (FI2) (angular, average particle size: about 70 μm) was placed in the container at a ratio of 109.2 parts by weight relative to 54.6 parts by weight of the aluminum hydroxide (FI1), and alumina (FI3) (spherical, average particle size: about 20 μm) was placed in the container at a ratio of 109.2 parts by weight relative to 54.6 parts by weight of the aluminum hydroxide (FI1), and further mixed with the stirred primary mixture (My1) to produce a secondary mixture (My2). The secondary mixture (My2) was stirred with a paste mixer at 500 rpm in the revolution direction and 400 rpm in the rotation direction until properly mixed, and then underwent a defoaming process at 500 rpm in the revolution direction and 150 rpm in the rotation direction to finally produce a curable composition (1).

[0176] The curable composition (1) contained the isocyanate compound (I), aluminum hydroxide (FI1), aluminum hydroxide (FI2), alumina (FI3), and additive (AI) at a weight ratio of 30:54.6:109.2:109.2:6.852 (I:FI1:FI2:FI3:AI). The isocyanate compound (I) and additive (AI) used were the same as those in Example 1.

[0177] (2) Production of curable composition (2) The curable composition (1) was mixed with the main agent part in the same manner as in Example 1 to produce a curable composition (2).

[0178] Comparative Example 5. (1) Production of curable composition (1) An isocyanate compound (I), aluminum hydroxide (FI1) (angular, average particle size: about 1 μm to 2 μm), and an additive (AI) were placed in a container at a weight ratio of 30:54.6:6.852 (I:FI1:AI) to produce a primary mixture (My1), which was initially stirred with a paste mixer at 500 rpm in the revolution direction and 400 rpm in the rotation direction until properly mixed. Aluminum hydroxide (FI2) (angular, average particle size: about 70 μm) was placed in the container at a ratio of 150.15 parts by weight with respect to 54.6 parts by weight of the aluminum hydroxide (FI1), and alumina (FI3) (spherical, average particle size: about 20 μm) was placed in the container at a ratio of 95.55 parts by weight with respect to 54.6 parts by weight of the aluminum hydroxide (FI1), and further mixed with the stirred primary mixture (My1) to produce a secondary mixture (My2). The secondary mixture (My2) was stirred with a paste mixer at 500 rpm in the revolution direction and 400 rpm in the rotation direction until properly mixed, and then underwent a defoaming process at 500 rpm in the revolution direction and 150 rpm in the rotation direction to finally produce a curable composition (1). The curable composition (1) contained the isocyanate compound (I), aluminum hydroxide (FI1), aluminum hydroxide (FI2), alumina (FI3), and additive (AI) at a weight ratio of 30:54.6:150.15:95.55:6.852 (I:FI1:FI2:FI3:AI). The isocyanate compound (I) and additive (AI) used were the same as those in Example 1.

[0179] (2) Production of curable composition (2) The curable composition (1) was mixed with the main agent part in the same manner as in Example 1 to produce a curable composition (2).

[0180] Comparative Example 6. (1) Production of curable composition (1) An isocyanate compound (I), aluminum hydroxide (FI1) (angular, average particle size: about 1 μm to 2 μm), a plasticizer (Pz), and an additive (AI) were placed in a container at a weight ratio of 30:54.6:4.5:6.852 (I:FI1:Pz:AI) to produce a primary mixture (My1), which was initially stirred with a paste mixer at 500 rpm in the revolution direction and 400 rpm in the rotation direction until properly mixed. Aluminum hydroxide (FI2) (angular, average particle size: about 70 μm) was placed in the container at a ratio of 109.2 parts by weight with respect to 54.6 parts by weight of the aluminum hydroxide (FI1), and alumina (FI3) (spherical, average particle size: about 20 μm) was placed in the container at a ratio of 109.2 parts by weight with respect to 54.6 parts by weight of the aluminum hydroxide (FI1). By further mixing with the stirred primary mixture (My1), a secondary mixture (My2) was produced. The secondary mixture (My2) was stirred with a paste mixer at 500 rpm in the revolution direction and 400 rpm in the rotation direction until properly mixed, and then a curable composition was produced through a defoaming process at 500 rpm in the revolution direction and 150 rpm in the rotation direction.

[0181] The curable composition (1) contained an isocyanate compound (I), aluminum hydroxide (FI1), aluminum hydroxide (FI2), alumina (FI3), a plasticizer (Pz), and an additive (AI) at a weight ratio of 30:54.6:109.2:109.2:4.5:6.852 (I:FI1:FI2:FI3:Pz:AI). The isocyanate compound (I), plasticizer (Pz), and additive (AI) used were the same as those in Example 1.

[0182] (2) Production of curable composition (2) The curable composition (1) was mixed with the main agent part in the same manner as in Example 1 to produce a curable composition (2).

[0183] The composition and each content ratio of the curable composition (1) are as shown in Table 1 below. In Table 1 below, FI1 is angular aluminum hydroxide with an average particle size of about 1 μm to 2 μm, and FI2 is angular aluminum hydroxide with an average particle size of about 70 μm. Also, in Table 1 below, FI3 is spherical alumina with an average particle size of about 20 μm, FI4 is angular alumina with an average particle size of about 1 μm to 2 μm, and FI5 is spherical alumina with an average particle size of about 70 μm.

[0184] [Table 1]

[0185] The physical properties measured for the curable compositions of the examples and comparative examples are summarized in Table 2 below. In Table 2, the viscosity change rate, density, and compatibility are for the curable composition (1) before being mixed with the main agent part, and the Shore A hardness and thermal conductivity are for the curable composition mixed with the main agent part.

[0186] [Table 2]

[0187] Referring to Table 2, it can be confirmed that the curable compositions of Examples 1 and 2 ensure a low viscosity change rate (VR) (storage stability) and low density characteristics. Also, referring to Table 2, it can be confirmed that the curable compositions of Examples 1 and 2 both have good compatibility and have the target level of Shore A hardness and thermal conductivity.

[0188] On the other hand, the curable compositions of Comparative Examples 1 and 2 have too high a density, the curable compositions of Comparative Examples 3 and 4 show too high a viscosity change rate (V R ) It can be confirmed that the curable composition of Comparative Example 5 has poor compatibility, and as a result, the viscosity change rate (V R ) could not be measured. Also, referring to Table 2, the curable composition of Comparative Example 6 did not ensure thermal conductivity and Shore A hardness.

Claims

1. A curable composition comprising an isocyanate compound, a filler component, and a plasticizer, having a density of 2.5 g / mL or less.

2. V of the following general formula (1) Ｒ The curable composition according to claim 1, wherein the content is 15% or less. 【General Formula 1】 V Ｒ = 100 × |V ｆ − V ｉ | / V ｉ In General Formula 1, V ｉ is the initial viscosity at normal temperature of the curable composition at a shear rate of 1.2 rpm, and V ｆ is the viscosity at normal temperature of the curable composition measured at a shear rate of 1.2 rpm after maintaining the curable composition at normal temperature for 240 hours.

3. The curable composition according to claim 1, comprising the filler component in the range of 70 to 95% by weight based on the total weight.

4. The curable composition according to claim 1, wherein the filler component contains a hydroxide filler.

5. The curable composition according to claim 4, wherein the content of the hydroxide filler in the filler component is in the range of 30 to 80% by weight.

6. The curable composition according to claim 1, wherein the filler component contains a first hydroxide filler having an average particle size of 60 μm or more and a second hydroxide filler having an average particle size of 10 μm or less.

7. The curable composition according to claim 6, wherein the ratio of the weight of the first hydroxide filler to the weight of the second hydroxide filler is in the range of 0.1 to 10.

8. The curable composition according to claim 6, wherein the ratio of the average particle size of the first hydroxide filler to the average particle size of the second hydroxide filler is in the range of 10 to 100.

9. The curable composition according to claim 4, wherein the filler component further contains a non-hydroxide filler.

10. The curable composition according to claim 9, wherein the filler component contains the non-hydroxide filler in a ratio in the range of 10 to 200 parts by weight based on 100 parts by weight of the hydroxide filler.

11. The curable composition according to claim 1, wherein the plasticizer contains at least one selected from the group consisting of phthalic acid compounds, phosphoric acid compounds, adipic acid compounds, sebacic acid compounds, citric acid compounds, glycolic acid compounds, trimellitic acid compounds, polyester compounds, epoxidized soybean oil, chlorinated paraffin, chlorinated fatty acid esters, fatty acid compounds, and vegetable oils.

12. The curable composition according to claim 4, containing 0.01 to 10 parts by weight of the plasticizer based on 100 parts by weight of the hydroxide filler.

13. The curable composition according to claim 1, wherein the isocyanate compound contains an aliphatic isocyanate compound.

14. The curable composition according to claim 1, wherein the isocyanate compound contains a diisocyanate compound and a polyisocyanate compound having three or more functional groups.

15. A curable composition comprising a main agent part containing a polyol compound and a curing agent part, wherein the curing agent part contains the curable composition according to claim 1.

16. The curable composition according to claim 15, which forms a cured product having a thermal conductivity of 3 W / m·K or more and a Shore A hardness of 80 or more according to ISO 22007-2 standard.

17. The curable composition according to claim 15, wherein the polyol compound includes a polyester polyol.

18. The curable composition according to claim 15, wherein the main agent part further includes a filler component.

19. Including a heating element and a cooling part, An apparatus including a cured product of the curable composition according to claim 15, which is in contact with the heating element and the cooling part.

20. A battery module including a cured product of the curable composition according to claim 15.

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