Resin composition

Abstract

The present invention relates to a resin composition, a two-component resin composition, and a battery module including the same. The present invention provides a resin composition that can maintain a uniform mixed state without oil separation even when a filler is blended, and does not increase in viscosity even during long-term storage. The present invention also provides a two-component resin composition including the resin composition, and a battery module including the resin composition or the two-component resin composition.

Description

Technical Field

[0001] Cross-reference to related applications This application claims the benefit of priority based on Korean Patent Application No. 10-2020-0126958, filed on September 29, 2020, and all the contents disclosed in the document of the Korean Patent Application are incorporated herein by reference.

[0002] Technical field The present invention relates to a resin composition having improved storage stability.

Background Art

[0003] TIM (Thermal Interface Material) materials are usually manufactured by blending fillers into resin components.

[0004] Such TIM materials can be used in various applications including battery modules and battery packs applied to electric vehicles.

[0005] As the resin component forming the TIM material, generally, an epoxy resin component, a polyurethane resin component, a polysilicon component, or the like is used.

[0006] However, such resin components commonly have a problem of a decrease in storage stability or storage stability.

[0007] For example, in the case of an epoxy resin component, an amide compound is usually used as a curing agent, but the amide compound reacts with moisture and rapidly increases the viscosity of the material. In addition, when an aliphatic series material is applied, there is also a problem that impurities such as salts are generated on the surface during long-term storage.

[0008] In the case of a polyurethane series material, an isocyanate compound is mainly used as a curing agent, but such a compound also easily reacts with moisture and induces an increase in the viscosity of the material.

[0009] In the case of polysilicon-based materials, since the compatibility with commonly applied fillers is generally poor, an oil separation phenomenon in which the filler and the resin component are separated easily occurs. Since it contains a low molecular weight siloxane component, when applied to electrical products, it easily induces issues such as poor contact.

[0010] In the case of the filler contained in the TIM material, it usually contains moisture by itself in many cases. However, the moisture contained in the filler in this way accelerates the above-mentioned problems.

[0011] Also, depending on the application of the TIM material, an excessive amount of filler is often blended to obtain high thermal conductivity. However, the use of an excessive amount of filler makes it even more difficult to solve the above problems.

Summary of the Invention

Problems to be Solved by the Invention

[0012] The present invention provides a resin composition. An object of the present invention is to provide a resin composition that does not have an oil separation phenomenon even in a composition containing a filler, can maintain a uniform mixing state, and does not have a viscosity increase even during long-term storage.

[0013] An object of the present invention is to provide a resin composition that can achieve the above object even when it contains an excessive amount of a filler that contains moisture and for which no separate surface treatment is carried out.

Means for Solving the Problems

[0014] Among the physical properties mentioned in this specification, when the measurement temperature affects the result, unless otherwise specified, the physical property is the physical property measured at room temperature. The term "room temperature" is the natural temperature without heating or cooling, and is usually any one temperature within the range of about 10°C to 30°C, or about 23°C or about 25°C. Also, unless otherwise specified in this specification, the unit of temperature is °C.

[0015] When the measured pressure affects the results among the physical properties mentioned in this specification, unless otherwise specified, the physical property is the physical property measured at normal pressure. The term "normal pressure" is the natural pressure without applying pressure or reducing pressure, and usually refers to about 1 atmosphere as normal pressure.

[0016] The present invention relates to a resin composition used in TIM (Thermal Interface Material) materials. TIM (Thermal Interface Material) materials can usually be manufactured by blending fillers into resin components. As resin components forming such TIM materials, generally, epoxy resin components, polyurethane resin components, polysilicon components, etc. can be used. However, the above-mentioned resin components commonly have poor storage stability or storage stability. In particular, when a TIM material contains a filler, it usually contains moisture itself in many cases, and the moisture contained in the filler can further deteriorate the storage stability or storage stability of the resin composition.

[0017] The resin composition according to the present invention contains a polymer compound having an organic acid anhydride functional group and a filler. When the resin composition contains a polymer compound having an organic acid anhydride functional group, it can effectively prevent the resin composition from reacting with moisture and increasing in viscosity. The moisture reacting with the resin composition can mean moisture existing outside the resin composition, moisture contained in the resin composition, or moisture contained in the filler.

[0018] As one example, the resin composition can satisfy the following general formula 1.

[0019] [General formula 1] V = V2 / V1 < 1.2

[0020] In General Formula 1, V is the viscosity change rate of the resin composition. V1 is the initial viscosity measured at room temperature and a shear rate of 2.4 / s within 3 minutes after manufacturing the resin composition containing a polymer compound having an organic acid anhydride functional group and a filler using a Wells / Brookfiled Cone & Plate viscometer. V2 is the viscosity measured at room temperature and a shear rate of 2.4 / s using a Wells / Brookfiled Cone & Plate viscometer 30 days after manufacturing the resin composition.

[0021] In the General Formula 1, the resin composition can be manufactured by blending a filler with a polymer compound having an organic acid anhydride functional group and mixing them with a mixer.

[0022] In the General Formula 1, as another example, the measurement of V1 may be the viscosity measured within about 2.5 minutes or about 2 minutes after manufacturing the resin composition.

[0023] In the General Formula 1, as another example, the viscosity change rate (V) of the resin composition may be about 1.19 or less, 1.18 or less, 1.17 or less, 1.16 or less, or about 1.15 or less. The lower limit is not particularly limited and may be about 1.00 or more or more than about 1.00.

[0024] As an example, the organic acid anhydride functional group may be a functional group derived from benzoic anhydride, a functional group derived from phthalic anhydride, or a functional group derived from maleic anhydride. A resin composition containing a polymer compound having an organic acid anhydride functional group of the above type has a low reaction with moisture, so it can effectively prevent an increase in the viscosity of the resin composition and may be advantageous in satisfying the above-described General Formula 1.

[0025] As an example, the polymer compound is not particularly limited as long as it satisfies the physical properties (molecular weight, glass transition temperature) described later. For example, it may be a compound having an organic acid anhydride functional group substituted on a polybutadiene skeleton, a polyester skeleton, or a polyether skeleton.

[0026] As an example, the polymer compound having the organic acid anhydride functional group may have a molecular weight (Mn) of 4,000 g / mol or less. As another example, the molecular weight (Mn) may be about 3,800 g / mol or less, 3,600 g / mol or less, 3,400 g / mol or less, 3,200 g / mol or less, or about 3,000 g / mol or less, and may also be about 500 g / mol or more, 600 g / mol or more, 700 g / mol or more, 800 g / mol or more, 900 g / mol or more, or about 1,000 g / mol or more.

[0027] A resin composition containing a polymer compound with a molecular weight (Mn) exceeding 4,000 g / mol may have a high viscosity change rate, resulting in a decrease in storage stability. When mixed with the main component part described later and applied to a battery module or a battery pack, it may induce an overload on the injection device. On the other hand, a resin composition containing a polymer compound with a molecular weight (Mn) less than 500 g / mol has an excessively low viscosity, so it takes a long time for the resin composition to cure. Therefore, the productivity of the battery module or the battery pack to which the resin composition is applied may decrease.

[0028] A resin composition containing a polymer compound having a molecular weight (Mn) within the above range may be more advantageous in satisfying the general formula 1 described above because of its low reactivity with moisture. When mixed with the main component part and applied to a battery module or a battery pack, it can prevent an overload on the injection device and can also improve the productivity of the battery module or the battery pack.

[0029] In this specification, the "molecular weight" may be the number average molecular weight (Mn) measured using GPC (Gel Permeation Chromatograph).

[0030] The number average molecular weight can be measured using GPC under the following conditions. At this time, for the preparation of the calibration curve, the measurement results can be converted using the standard polystyrene of the Agilent system.

[0031] <Molecular weight measurement conditions>

[0032] Measuring instrument: Gel Permeation Chromatography (Waters Alliance System)

[0033] Column: PL Mixed B type

[0034] Detector: Refractive index detector

[0035] Column flow rate and solvent: 1 mL / min, Solvent: THF (Tetrahydrofuran)

[0036] Analysis temperature and measurement volume: 40 °C, 200 μL

[0037] As an example, the polymer compound having the organic acid anhydride functional group may have a glass transition temperature of 0 °C or lower. As another example, it may be about -5 °C or lower, about -10 °C or lower, about -15 °C or lower, about -20 °C or lower, about -25 °C or lower, about -30 °C or lower, about -35 °C or lower, about -40 °C or lower, about -45 °C or lower, or about -50 °C or lower, and may also be about -150 °C or higher, -140 °C or higher, -130 °C or higher, -120 °C or higher, or about -100 °C or higher. The glass transition temperature can be measured using DMA (Dynamic mechanical analyzer) or Differential Scanning Calorimetry (DSC), etc.

[0038] A resin composition containing a polymer compound whose glass transition temperature satisfies the above range is less reactive with moisture, and thus may be more advantageous in satisfying the above-mentioned general formula 1.

[0039] As an example, the polymer compound may have an acid value within the range of 50 mgKOH / g to 120 mgKOH / g according to DIN EN ISO 2114. As another example, the acid value may be about 52 mgKOH / g or more, 54 mgKOH / g or more, 56 mgKOH / g or more, 58 mgKOH / g or more, or about 60 mgKOH / g or more, and may be about 118 mgKOH / g or less, 116 mgKOH / g or less, 114 mgKOH / g or less, 112 mgKOH / g or less, or about 110 mgKOH / g or less.

[0040] A resin composition containing a polymer compound satisfying the acid value within the above range has low reactivity with moisture, so that an increase in the viscosity of the resin composition can be effectively prevented, and it can be more advantageous in satisfying the above-mentioned general formula 1.

[0041] As an example, the polymer compound may contain a polymerization unit of the following Chemical Formula 1.

[0042]

Chemical Formula

[0043] In Chemical Formula 1, L1 is a single bond or an alkenylene group having 2 to 4 carbon atoms, L2 is a single bond or an alkylene group having 1 to 4 carbon atoms, and L3 and L4 are each independently a single bond or an alkylene group having 1 to 4 carbon atoms.

[0044] Further, the polymer compound may additionally contain a polymerization unit of the following Chemical Formula 2.

[0045]

Chemical Formula

[0046] In Chemical Formula 2, L5 is an alkenylene group having 2 to 4 carbon atoms or an alkylene group having 1 to 4 carbon atoms substituted with an alkenyl group having 2 to 4 carbon atoms.

[0047] The polymer compound containing the polymerization unit of Chemical Formula 1 and the polymerization unit of Chemical Formula 2 has low reactivity with moisture, so it can more effectively prevent the viscosity increase of the resin composition, and can be more advantageous in satisfying the general formula 1 described above.

[0048] The resin composition according to the present invention contains a filler. The filler may be a heat-conductive filler. The term "heat-conductive filler" in the present invention can mean a filler made of a material having a thermal conductivity of about 3 W / mK or more, 5 W / mK or more, 10 W / mK or more, or about 15 W / mK or more. Specifically, the thermal conductivity of the heat-conductive filler may be about 400 W / mK or less, 350 W / mK or less, or about 300 W / mK or less. The type of heat-conductive filler that can be used is not particularly limited, but when considering insulation and the like together, it may be an inorganic filler. For example, ceramic particles such as aluminum oxide (alumina: Al2O3), aluminum nitride (AlN), boron nitride (BN), silicon nitride (Si3N4), silicon carbide (SiC), beryllium oxide (BeO), zinc oxide (ZnO), magnesium oxide (MgO), or boehmite can be used. The form and ratio of the filler are not particularly limited and can be appropriately adjusted in consideration of the viscosity of the resin composition, the viscosity change rate of the resin composition, dispersibility, storage stability, etc. Generally, the larger the size of the filler, the higher the viscosity of the composition containing it, and the higher the possibility of the filler settling. Also, the smaller the size, the higher the thermal resistance tends to be. Therefore, an appropriate type and size of filler can be selected in consideration of the above points, and if necessary, two or more kinds of fillers may be used together. Also, considering the amount to be filled, it is advantageous to use spherical fillers, but fillers in the form of needles or plates can also be used in consideration of network formation and conductivity.

[0049] In one example, the filler may have an average particle size in the range of about 0.001 μm to 80 μm. In other examples, the average particle size of the filler may be about 0.01 μm or more, 0.1 μm or more, 0.5 μm or more, 1 μm or more, 2 μm or more, 3 μm or more, 4 μm or more, 5 μm or more, or about 6 μm or more. In other examples, the average particle size of the filler may be about 75 μm or less, 70 μm or less, 65 μm or less, 60 μm or less, 55 μm or less, 50 μm or less, 45 μm or less, 40 μm or less, 35 μm or less, 30 μm or less, 25 μm or less, 20 μm or less, 15 μm or less, 10 μm or less, or about 5 μm or less.

[0050] To obtain excellent heat dissipation performance, it may be considered to use a high content of the thermal conductive filler. The filler used in the high content can be included in the range of 75% by weight to 92% by weight based on 100% by weight of the resin composition. Specifically, the content of the filler can be about 76% by weight or more, 77% by weight or more, 78% by weight or more, 79% by weight or more, or about 80% by weight or more, and can include about 91.5% by weight or less, 91% by weight or less, 90.5% by weight or less, or about 90% by weight or less based on 100% by weight of the resin composition. Physical properties such as the desired thermal conductivity and storage stability can be ensured within the proportion range of the filler.

[0051] In one example, the moisture content of the filler is not particularly limited. For example, it may be about 10 ppm or more, about 100 ppm or more, or about 1,000 ppm or more, and may be about 3,000 ppm or less, 2,900 ppm or less, or about 2,800 ppm or less. The moisture content of the filler can be measured with a Karl Fischer titrator (KR831) under the conditions of a relative humidity of 10% and a drift of 5.0 or less. At this time, the moisture content may be the average moisture content with respect to the total filler used in the resin composition.

[0052] The resin composition required a filler pretreatment step such as reducing the moisture content of the filler to lower the viscosity change rate due to moisture, or surface-treating the filler to prevent oil separation. The resin composition containing a polymer compound having an organic acid anhydride functional group according to the present invention has low reactivity with moisture even when the water content contained in the filler is in the range of 10 ppm to 3,000 ppm, so the viscosity change of the resin composition is not large. Therefore, the storage stability of the resin composition can be greatly improved. In addition, since the filler pretreatment step is not essentially accompanied, the manufacturing cost can be reduced, and the manufacturing processability is improved.

[0053] In addition to the above, various types of fillers can be used. For example, in order to ensure the insulation properties of the cured product obtained by curing the resin composition, the use of carbon fillers such as graphite can be considered. Or, for example, fillers such as fumed silica, clay, calcium carbonate (CaCO3), zinc oxide (ZnO), or aluminum hydroxide (Al(OH)3) can be used. The form and content ratio of such fillers are not particularly limited and can be selected in consideration of the viscosity, viscosity change rate, sedimentation possibility, thixotropy, insulation property, filling effect, or storage stability of the resin composition.

[0054] As an example, the resin composition may not contain an amine catalyst and an isocyanate compound. Examples of the amine catalyst include, but are not limited to, 2-4-6 tris(dimethylaminomethyl)phenol, N,N-Dimenthylpropionamide, Imidazole, 1,4-diazabicyclo(2,2,2)octane, bis(2-dimethylaminoethyl)ether, trimethylaminoethylethanolamine, pentamethyldiethylenetriamine, N,N’-dimethylethanolamine, Dimethylaminopropylamine, N-ethylmorpholine, N,N-dimethylaminoethylmorpholine, N,N-dimethylcyclohexylamine, or 2-methyl-2-azanorbornane. Also, the type of the isocyanate compound is not particularly limited, and examples thereof may include known aromatic isocyanate compounds or non-aromatic isocyanate compounds.

[0055] The polymer compound having an organic acid anhydride functional group can react with water in the presence of an amine catalyst, which may induce an increase in the viscosity of the resin composition. Therefore, the storage stability of the resin composition may decrease. Also, when an isocyanate compound is present in the resin composition, it can react with water to also induce an increase in the viscosity of the resin composition.

[0056] When the resin composition does not contain an amine catalyst and an isocyanate compound, the moisture reactivity of the resin composition significantly decreases, and the storage stability of the resin composition can be further improved.

[0057] The present invention also relates to a two-component resin composition. The two-component resin composition according to the present invention can include a main agent part containing a main agent resin and a filler; and a curing agent part. On the other hand, the curing agent part can mean the resin composition described above, that is, a resin composition containing a polymer compound having an organic acid anhydride functional group and a filler. Therefore, the content related to the resin composition described above and the components constituting the resin composition can be equally applied to the two-component resin composition.

[0058] As an example, the filler contained in the main agent part can use the above-described thermal conductive filler.

[0059] The main agent resin can use a polyol resin, specifically, an ester polyol resin can be used. The ester polyol may be a non-crystalline or sufficiently low-crystallinity polyol.

[0060] In this specification, "non-crystalline" means a case where a crystallization temperature (Tc) and a melting temperature (Tm) are not observed in a DSC (Differential Scanning Calorimetry) analysis described later. At this time, the DSC analysis can be performed in the range of -80 to 60 °C at a rate of 10 °C / min. For example, it can be performed in a manner of heating from 25 °C to 60 °C at the above rate and then cooling to -80 °C again and heating to 60 °C again. Also, "sufficiently low crystallinity" as described above means that the melting point (Tm) observed in the DSC analysis is less than 15 °C, and is about 10 °C or lower, 5 °C or lower, 0 °C or lower, -5 °C or lower, -10 °C or lower, or about -20 °C or lower. At this time, the lower limit of the melting point is not particularly limited. For example, the melting point may be about -80 °C or higher, -75 °C or higher, or about -70 °C or higher. When the polyol does not satisfy the crystallinity or the melting point range and has strong crystallinity (at room temperature), the viscosity difference due to temperature tends to be large, so the manufacturability in the manufacturing process may decrease.

[0061] In one example, as the ester polyol, for example, carboxylic acid polyol or caprolactone polyol can be used.

[0062] The carboxylic acid polyol can be formed by reacting a component containing a carboxylic acid and a polyol (for example, a diol or a triol, etc.), and the caprolactone polyol can be formed by reacting a component containing caprolactone and a polyol (for example, a diol or a triol, etc.). At this time, the carboxylic acid may be a dicarboxylic acid.

[0063] The main agent part and the curing agent part can react and cure at room temperature. Specifically, the ester polyol resin in the main agent part and the polymer compound having an organic acid anhydride functional group in the curing agent part can react and be cured at room temperature.

[0064] The curing reaction can be assisted by, for example, a catalyst. Thereby, the two-component resin composition can include all of the states where the main agent resin (polyol) and the curing agent (polymer compound having an organic acid anhydride functional group) are separated, mixed, or reacted.

[0065] As the catalyst that can accelerate the reaction between the main resin and the curing agent, an amine catalyst can be used. For example, 2-4-6 tris(dimethylaminomethyl)phenol, N,N-Dimenthylpropionamide, Imidazole, 1,4-diazabicyclo(2,2,2)octane, bis(2-dimethylaminoethyl)ether, trimethylaminoethylethanolamine, pentamethyldiethylenetriamine, N,N’-dimethylethanolamine, Dimethylaminopropylamine, N-ethylmorpholine, N,N-dimethylaminoethylmorpholine, N,N-dimethylcyclohexylamine, or 2-methyl-2-azanorbornane, at least one of them can be used.

[0066] The catalyst can be contained in the main agent part within the range of about 0.01% by weight to 5% by weight based on 100% by weight of the two-component resin composition. When the catalyst is contained in the main agent part within the above range, it is advantageous for improving the storage stability of the two-component resin composition. Also, during the injection of the two-component resin composition, since the viscosity of the two-component resin composition is low, the manufacturing processability is improved. After injection, the curing rate of the two-component resin composition is accelerated, and the process tact time of the battery module can be improved.

[0067] In the two-component resin composition, a dispersant can be additionally included in at least one of the main agent part and the curing agent part. Considering the viscosity and storage stability of the target resin composition, a copolymer phosphate dispersant containing a propylene glycol methyl ether group can be used as the type of the dispersant. On the other hand, as an example, when the dispersant is included in both the main agent part and the curing agent part, the content of the dispersant in the main agent part can be included in the range of 0.05% by weight to 10% by weight based on 100% by weight of the two-component resin, and the dispersant included in the curing agent part can be included in the range of 0.01% by weight to 5% by weight based on 100% by weight of the two-component resin.

[0068] When the phosphate-based dispersant as described above is used in the main agent part and the curing agent part at the above-mentioned content ratios, the viscosity change of the two-component resin composition can be reduced, and oil separation can be more effectively prevented.

[0069] As an example, the two-component resin composition can form a cured product having a thermal conductivity of 2.0 W / mK or more measured according to the ISO22007-2 standard. As another example, it may be about 2.5 W / mK or more, 3.0 W / mK or more, 3.5 W / mK or more, or 4.0 W / mK or more, and may also be about 50 W / mK or less, 45 W / mK or less, 40 W / mK or less, 35 W / mK or less, 30 W / mK or less, 25 W / mK or less, 20 W / mK or less, 15 W / mK or less, 10 W / mK or less, 5 W / mK or less, 4.5 W / mK or less, or about 4.0 W / mK or less. When the cured product of the two-component resin composition satisfies the thermal conductivity in the above range, the heat dissipation performance of the battery module or battery pack to which the two-component resin composition is applied can be improved.

[0070] Furthermore, the present invention relates to a battery module. The battery module includes a module case and battery cells existing inside the module case. The battery cells may be housed in the module case. One or more battery cells may exist in the module case, and a plurality of battery cells may be housed in the module case. The number of battery cells housed in the module case is adjusted according to applications etc. and is not particularly limited. The battery cells housed in the module case may be electrically connected to each other.

[0071] Furthermore, the battery module according to the present invention includes a resin layer in contact with the plurality of battery cells and the module case. The resin layer may be a cured layer of a resin composition including a polymer compound having the organic acid anhydride functional group described above and a filler, or a cured layer of the two-component resin composition described above.

[0072] Furthermore, the present invention relates to a battery pack, for example, a battery pack including two or more of the above-described battery modules. In the battery pack, the battery modules may be electrically connected to each other. The method of electrically connecting two or more battery modules to form a battery pack is not particularly limited, and all known methods can be applied.

Advantages of the Invention

[0073] The resin composition according to the present invention can maintain a uniform mixed state without an oil separation phenomenon even in a composition containing a filler, and can prevent or reduce an increase in viscosity even during long-term storage. Further, the resin composition according to the present invention can achieve the above-described effects even when it particularly contains moisture and contains an excessive amount of a filler in a state where no separate surface treatment is performed.

Embodiments for Carrying Out the Invention

[0074] Hereinafter, the present invention will be described with specific examples through embodiments, but the scope of the present invention is not limited by the following embodiments.

[0075] Evaluation of storage stability The storage stability was evaluated using the curing agent parts (resin compositions) produced in the examples and comparative examples. When the value of the following General Formula 1 is 1.2 or more, it was evaluated that there is no storage stability.

[0076] [General Formula 1] V = V2 / V1 < 1.2

[0077] In General Formula 1, V is the viscosity change rate of the resin composition, V1 is the initial viscosity measured at room temperature and a shear rate of 2.4 / s within 3 minutes after producing the resin composition containing the polymer compound having an organic acid anhydride functional group and the filler using a Wells / Brookfiled Cone & Plate viscometer, and V2 is the viscosity measured at room temperature and a shear rate of 2.4 / s at the time when 30 days have elapsed after producing the resin composition using a Wells / Brookfiled Cone & Plate viscometer.

[0078] Also, when white crystals are generated due to salt generation or an oil separation phenomenon is observed within 3 days after producing the resin composition, it was evaluated that there is no storage stability.

[0079] <Evaluation Criteria> ○: The value of the above General Formula 1 is less than 1.2, no salt generation, and no oil separation phenomenon is observed within 3 days (when all are applicable) ×: The value of the above General Formula 1 is 1.2 or more, salt generation is present, and an oil separation phenomenon is observed within 3 days (when any one is applicable)

[0080] Thermal conductivity Using the cured products of the main agent part and the curing agent part produced in the examples and comparative examples, a two-component resin composition produced using a static mixer was measured by the Hot Disk method according to the ISO22007-2 standard. At this time, the two-component resin composition was produced such that the volume ratio of the main agent part and the curing agent part was about 1:1.

[0081] Specifically, for the measurement of thermal conductivity, the cured product of the two-component resin composition can be placed in a mold with a thickness of about 5 mm, and the thermal conductivity can be measured in the through plane direction using a Hot Disk device. As defined in the said standard (ISO 22007-2), the Hot Disk device is a device capable of measuring the thermal conductivity by measuring the temperature change (change in electrical resistance) while heating a sensor in which a nickel wire has a double spiral structure. The thermal conductivity was measured according to such a standard.

[0082] Examples Main agent part: As the main agent resin, caprolactone polyol represented by the following Chemical Formula 3 was used.

[0083]

Chemical formula

[0084] In Chemical Formula 3, m is a number in the range of 1 to 3, R1 and R2 are each alkylene having 4 carbon atoms, and Y is a 1,4-butanediol unit.

[0085] As the filler, alumina was used, and the one without any treatment on the particle surface was used as it was.

[0086] As the catalyst, DMP-30 (2-4-6 tris(dimethylaminomethyl)phenol) of Daejungchem was used, and as the dispersant, BKY-111 of BYK was used.

[0087] The main agent part was manufactured by mixing the caprolactone polyol, filler, catalyst, and dispersant at a weight ratio of 10.36:89:0.34:0.3 (polyol:filler:catalyst:dispersant).

[0088] Hardener part (resin composition): As the polymer compound having an organic acid anhydride functional group, POLYVEST MA 75 from EVONIK was used (number average molecular weight: 3,000 g / mol, glass transition temperature: -95 °C, acid value: 70 - 90 mgKOH / g).

[0089] As the filler, alumina was used, and the one with no treatment on the particle surface was used as it was.

[0090] As the dispersant, BKY - 118 from BYK was used.

[0091] The hardener part was manufactured by mixing the polymer compound having the organic acid anhydride functional group, filler, and dispersant at a weight ratio of 10.85:89:0.15 (polymer compound:filler:dispersant).

[0092] The mixing during the manufacture of the main agent part and the hardener part was carried out using a planetary mixer.

[0093] Comparative example 1 Main agent part: It was manufactured by mixing with the same components and ratios as in the example, except that Tin catalyst (DBTDL from Sigma - Aldrich) was used instead of the amine catalyst.

[0094] Hardener part: It was manufactured by mixing with the same components and ratios as in the example, except that polyisocyanate (HDI, Hexamethylene diisocyanate) was used instead of the polymer compound in the example, and BKY - 111 from BYK was used as the dispersant.

[0095] Comparative example 2 Main agent part: Except that epoxy resin (YH-300 of Kokoku Chemical Co., Ltd.) was used instead of polyol resin as the main agent resin and BKY-102 of BYK was used as the dispersant, it was manufactured by mixing with the same components and ratios as in the examples.

[0096] Hardener part: Except that amide (G-A0432 of Kokoku Chemical Co., Ltd.) was used instead of the high molecular compound in the examples and BKY-102 of BYK was used as the dispersant, it was manufactured by mixing with the same components and ratios as in the examples.

[0097] Comparative example 3 Main agent part: It was manufactured by mixing with the same components and ratios as in Comparative Example 2.

[0098] Hardener part: Except that aliphatic amine (KH-8108 of Kokoku Chemical Co., Ltd.) was used instead of the high molecular compound in the examples and BKY-102 of BYK was used as the dispersant, it was manufactured by mixing with the same components and ratios as in the examples.

[0099] Comparative example 4 Main agent part: Except that siloxane (SF3000E, SF6003P, Modifier715 and Inhibitor600 of KCC) was used as the main agent resin and BYK-1799 of BYK was used as the dispersant, it was manufactured by mixing with the same components and ratios as in the examples.

[0100] Hardener part: Except that siloxane (SF3000E of KCC) was used instead of the high molecular compound in the examples and BYK-1799 of BYK was used as the dispersant, it was manufactured by mixing with the same components and ratios as in the examples.

[0101] The storage stability evaluation and thermal conductivity measured for the above examples and comparative examples were organized and listed in Table 1 below.

[0102]

Table 1

[0103] From the results in Table 1, it can be seen that in the case of the examples in which the resin composition contains a polymer compound having an organic acid anhydride functional group, even when the water content of the filler is adjusted or the surface of the filler is treated, the storage stability is excellent. Further, the cured product of the two-component resin composition containing the resin composition in the curing agent part had an excellent thermal conductivity of 2.0 W / mK or more.

[0104] In comparison, in the case of Comparative Example 1 in which isocyanate is contained instead of the polymer compound having an organic acid anhydride functional group in the resin composition, or in the case of Comparative Example 2 in which amide is contained instead of the polymer compound having an organic acid anhydride functional group in the resin composition, it can be seen that the viscosity change rate exceeds 1.2 and the storage stability deteriorates. Further, in the case of Comparative Example 3 in which an aliphatic amine is contained instead of the polymer compound having an organic acid anhydride functional group in the resin composition, white crystals due to salt generation were formed. Further, in the case of Comparative Example 4 in which siloxane is contained instead of the polymer compound having an organic acid anhydride functional group in the resin composition, it can be seen that an oil separation phenomenon is observed within 3 days after producing the resin composition and the storage stability deteriorates.

Claims

1. A main agent part containing a main agent resin and a filler; and a curing agent part, wherein the curing agent part contains a polymer compound having an organic acid anhydride functional group and a filler, the polymer compound having an organic acid anhydride functional group has a number average molecular weight (Mn) of 500 g / mol or more and 4,000 g / mol or less, the curing agent part contains the filler within a range of 75% by weight to 92% by weight based on 100% by weight of the curing agent part, The filler includes one or more selected from the group consisting of aluminum oxide (Al ２ O ３ ), aluminum nitride (AlN), boron nitride (BN), silicon nitride (Si ３ N ４ ), silicon carbide (SiC), beryllium oxide (BeO), zinc oxide (ZnO), aluminum hydroxide (Al(OH) ３ ), boehmite, and carbon fillers. the curing agent part is a two-component resin composition that does not contain an amine catalyst and an isocyanate compound.

2. The two-component resin composition according to claim 1, wherein the organic acid anhydride functional group is a functional group derived from benzoic anhydride, a functional group derived from phthalic anhydride, or a functional group derived from maleic anhydride.

3. The two-component resin composition according to claim 1 or 2, wherein the polymer compound having an organic acid anhydride functional group has an organic acid anhydride functional group substituted on a polybutadiene skeleton, a polyester skeleton, or a polyether skeleton.

4. The two-component resin composition according to any one of claims 1 to 3, wherein the polymer compound having an organic acid anhydride functional group has a glass transition temperature (Tg) of 0°C or lower.

5. The two-component resin composition according to any one of claims 1 to 4, wherein the polymer compound having an organic acid anhydride functional group has an acid value in the range of 50 mgKOH / g to 120 mgKOH / g according to DIN EN ISO 2114.

6. The two-component resin composition according to any one of claims 1 to 5, wherein the polymer compound having an organic acid anhydride functional group contains a polymerization unit of the following Chemical Formula 1. 【Chemical 1】 In Chemical Formula 1, L １ is a single bond or an alkenylene group having 2 to 4 carbon atoms, and L ２ is a single bond or an alkylene group having 1 to 4 carbon atoms, and L ３ and L ４ are each independently a single bond or an alkylene group having 1 to 4 carbon atoms.

7. The two-component resin composition according to any one of claims 1 to 6, wherein the polymer compound having an organic acid anhydride functional group additionally contains a polymerization unit of the following Chemical Formula 2. 【Chemical 2】 In Chemical Formula 2, L ５ is an alkylene group having 1 to 4 carbon atoms substituted with an alkenylene group having 2 to 4 carbon atoms or an alkenyl group having 2 to 4 carbon atoms.

8. The two-component resin composition according to any one of claims 1 to 7, wherein the filler has a moisture content in the range of 10 ppm to 3,000 ppm.

9. The two-component resin composition according to any one of claims 1 to 8, wherein the main agent resin is a polyol resin.

10. The two-component resin composition according to any one of claims 1 to 9, wherein the main agent part additionally contains an amine catalyst.

11. The two-component resin composition according to any one of claims 1 to 10, wherein at least one of the main agent part and the curing agent part additionally contains a dispersant.

12. Module case; including a plurality of battery cells housed in the internal space of the module case and a resin layer in contact with the plurality of battery cells and the module case, wherein the resin layer is a cured layer of the two-component resin composition according to any one of claims 1 to 11, a battery module.

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