Curable composition

Abstract

The present application provides a curable composition which has appropriate viscosity and thixotropy before and after curing even when containing an excessive amount of fillers, and shows no particle sedimentation even during long-term storage. The curable composition contains a polyolefin binder having an acid anhydride unit, fillers, and a dispersant, and the dispersant contains a polymer compound having a specific structure.

Description

Technical Field

[0001] Cross - reference to related applications

[0002] This application claims the benefit of priority based on Korean Patent Application No. 10-2020-0127535, filed on September 29, 2020, the disclosure of which is incorporated herein by reference in its entirety. Technical Field

[0004] This application relates to a curable composition. Background Art

[0005] As the handling of heat generated from electrical products, electronic products, or batteries such as secondary batteries has become an important issue, various heat dissipation countermeasures have been proposed.

[0006] Among the heat conductive materials for heat dissipation countermeasures, resin compositions in which heat conductive fillers are mixed with resins are known.

[0007] In particular, a curable composition may contain an excessive amount of filler to ensure heat dissipation (thermal conductivity) or to ensure thixotropy according to process requirements.

[0008] When an excessive amount of filler is added to and mixed with a resin, there is a problem of filler sedimentation due to poor dispersion and a decrease in the thixotropy index (T.I.). Therefore, even when mixing an excessive amount of filler, it is intended to improve the dispersibility by using a dispersant, but there is a problem that the compatibility decreases according to the type of resin, or the dispersant reacts with the resin. Therefore, it is important to use a dispersant having excellent compatibility and non-reactive characteristics according to the type of resin.

[0009] Patent Document 1 (Japanese Patent Publication No. 5218364) relates to a thermally conductive composition that maintains stable syringe discharge performance at room temperature, in which a dispersant is used to improve the dispersibility of the resin and the filler, but the dispersant is not selected in consideration of excellent compatibility and non-reactive characteristics.

[0010] In addition, even when the dispersant has excellent compatibility and non-reactive characteristics with a specific resin during mixing, there is a problem of filler sedimentation during long-term storage.

[0011] Specifically, in the case of mixing a polymer containing a maleic anhydride unit with a filler, when an amine-based dispersant is applied, there is a problem that the polymer reacts with the amine-based dispersant and cures. Therefore, when using an amine-based dispersant, the compatibility decreases and mixing cannot be performed, and thus a cured product cannot be formed.

[0012] In addition, when mixing a filler with a polymer containing maleic anhydride units, a phosphoric acid copolymer dispersant can be applied. However, in the case where the dispersant structure does not have a propylene glycol methyl ether structure, there is a problem of particle sedimentation when the curable composition is left standing for a long time. Summary of the Invention

[0013] Technical Problem

[0014] The present application aims to provide a curable composition capable of solving the above problems.

[0015] The present application aims to provide a curable composition which, even when containing an excessive amount of filler, has appropriate viscosity and thixotropy before and after curing.

[0016] The present application aims to provide a curable composition that does not exhibit any particle sedimentation even during long-term storage.

[0017] Technical Solution

[0018] In one example according to the present application, the present application relates to a curable composition which has appropriate viscosity and thixotropy before and after curing and does not exhibit particle sedimentation even during long-term storage. Here, the curable composition may contain a polyolefin binder having an acid anhydride unit, a filler, and a dispersant. This also means that particles can be settled in the curable composition.

[0019] The curable composition according to the present application may contain a dispersant, wherein the dispersant may be a polymer compound containing a unit of the following formula 1.

[0020] [Formula 1]

[0021]

[0022] In the above formula 1, L1 may be an alkylene group having 3 to 8 carbon atoms, L2 may be a methylene group or an ethylene group, and p / q may be a value in the range of 0.1 to 10.

[0023] In the above formula 1, L1 is preferably an alkylene group having 3 to 6 carbon atoms, an alkylene group having 3 to 5 carbon atoms, or an alkylene group having 3 to 4 carbon atoms, and among them, the alkylene group is more preferably a branched alkylene group.

[0024] The polymer compound containing the unit of the above formula 1 may be, for example, a unit formed by copolymerizing polypropylene glycol, polyethylene glycol, and phosphoric acid. That is, the polymer compound containing the unit of the above formula 1 can be formed by copolymerization.

[0025] In another example, p / q can be a value in the range of 0.5 to 2, a value in the range of 0.75 to 1.25, or a value in the range of 0.8 to 1.2. p and q can be selected as appropriate values while satisfying the above ranges by the number average molecular weight (M n ) of the polymer compound containing the unit of Formula 1 described below, the weight average molecular weight (M w ) and the polydispersity index (PDI). When the value of p / q satisfies the above ranges, even after mixing a polyolefin binder having an acid anhydride unit with a filler, appropriate thixotropy can be ensured.

[0026] The curable composition according to the present application can prevent the sedimentation phenomenon of particles even during long-term storage by using a polymer compound containing the unit of Formula 1 above as a dispersant.

[0027] The weight average molecular weight of the polymer compound containing the unit of Formula 1 above can be 5,000 g / mol or more, 6,000 g / mol or more, 7,000 g / mol or more, 8,000 g / mol or more, 9,000 g / mol or more, 10,000 g / mol or more, 11,000 g / mol or more, 12,000 g / mol or more, 13,000 g / mol or more, 14,000 g / mol or more, 15,000 g / mol or more, or 16,000 g / mol or more, and in another example, the weight average molecular weight of the polymer compound containing the unit of Formula 1 above can be 40,000 g / mol or less, 35,000 g / mol or less, 30,000 g / mol or less, 25,000 g / mol or less, 20,000 g / mol or less, or 18,000 g / mol or less. The weight average molecular weight can be measured using GPC (gel permeation chromatography).

[0028] In addition, the number average molecular weight of the polymer compound containing the unit of Formula 1 can be 4,000 g / mol or more, 5,000 g / mol or more, 6,000 g / mol or more, 7,000 g / mol or more, 8,000 g / mol or more, 9,000 g / mol or more, 10,000 g / mol or more, 11,000 g / mol or more, or 12,000 g / mol or more, and in another example, the number average molecular weight of the polymer compound containing the unit of Formula 1 above can be 35,000 g / mol or less, 30,000 g / mol or less, 25,000 g / mol or less, 20,000 g / mol or less, or 15,000 g / mol or less. The number average molecular weight can also be measured using GPC.

[0029] In addition, the polydispersity index (PDI) of the polymer compound of the unit containing Formula 1 may be in the range of 0.8 to 2, preferably in the range of 1 to 1.5.

[0030] When the weight-average molecular weight, number-average molecular weight, and polydispersity index of the polymer compound of the unit containing Formula 1 satisfy the above ranges, the polyolefin binder and the filler having an acid anhydride unit have excellent processability even after they are mixed. Thus, they are easy to handle, and long-term storage stability thereof can be ensured.

[0031] Relative to the total weight of the curable composition, the content of the dispersant may be 0.05% by weight or more, 0.1% by weight or more, 0.15% by weight or more, 0.2% by weight or more, or 0.25% by weight or more. In another example, relative to the total weight of the curable composition, the content of the dispersant may be 1% by weight or less, 0.75% by weight or less, 0.5% by weight or less, 0.4% by weight or less, or 0.3% by weight or less. When the content of the dispersant satisfies the above range, compatibility and long-term storage stability can be ensured.

[0032] In another example, relative to 100 parts by weight of the polyolefin binder described below, the content of the dispersant may be 1 part by weight or more, 2 parts by weight or more, 3 parts by weight or more, or 4 parts by weight or more, and may be 10 parts by weight or less, 9 parts by weight or less, 8 parts by weight or less, or 6 parts by weight or less. When the content of the dispersant satisfies the above range, compatibility and long-term storage stability can be ensured.

[0033] Relative to the total weight of the dispersant, the polymer compound of the unit containing Formula 1 may be contained in an amount of 50% by weight or more, 55% by weight or more, 60% by weight or more, 65% by weight or more, 70% by weight or more, 75% by weight or more, or 80% by weight or more.

[0034] The dispersant of the curable composition according to the present application may further contain an ester compound to ensure better dispersibility.

[0035] The ester compound may be selected from, for example, alkylene glycol monoalkyl ether acetates, alkoxy propionic acid alkyl esters, alkylene glycol monoalkyl ether propionates, alkylene glycol diacetates, alkyl lactates, and alkyl 2-hydroxyisoalkylates. The ester compound is preferably an alkylene glycol monoalkyl ether acetate.

[0036] Unless otherwise described, the term alkyl or alkylene used herein may be a straight-chain or branched-chain acyclic alkyl or alkylene having 1 to 20 carbon atoms, or 1 to 16 carbon atoms, or 1 to 12 carbon atoms, or 1 to 8 carbon atoms, 1 to 6 carbon atoms, or 1 to 4 carbon atoms, or may be a cyclic alkyl or alkylene 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, or may be a saturated hydrocarbon group bonded thereto.

[0037] The alkylene glycol monoalkyl ether acetates include, for example, methylene glycol monomethyl ether acetate, methylene glycol monoethyl ether acetate, ethylene glycol monomethyl ether acetate, and ethylene glycol monoethyl ether acetate, etc.

[0038] The alkoxy propionic acid alkyl esters include, for example, methyl methoxypropionate, methyl ethoxypropionate, ethyl methoxypropionate, and ethyl ethoxypropionate, etc.

[0039] The alkylene glycol monoalkyl ether propionates include, for example, methylene glycol monomethyl ether propionate, ethylene glycol monomethyl ether propionate, methylene glycol monoethyl ether propionate, and ethylene glycol monoethyl ether propionate, etc.

[0040] The alkylene glycol diacetates include, for example, methylene glycol diacetate and ethylene glycol diacetate, etc.

[0041] The alkyl lactates include, for example, methyl lactate, ethyl lactate, and butyl lactate, etc.

[0042] The 2-hydroxyisobutyric acid alkyl esters include, for example, methyl 2-hydroxyisobutyrate, methyl 2-hydroxyacetate, ethyl 2-hydroxyisobutyrate, and butyl 2-hydroxyisobutyrate, etc.

[0043] With respect to the total weight of the dispersant, the content of the ester compound may be 5% by weight or more, 7.5% by weight or more, 10% by weight or more, 12.5% by weight or more, 15% by weight or more, 17.5% by weight or more, or 20% by weight or more. In another example, with respect to the total weight of the dispersant, the content of the ester compound may be 40% by weight or less, 38% by weight or less, 36% by weight or less, 34% by weight or less, 32% by weight or less, 30% by weight or less, 28% by weight or less, 26% by weight or less, 24% by weight or less, 22% by weight or less, or 20% by weight or less.

[0044] In addition to the polymer compound containing the unit of Formula 1 and the ester compound, other types of dispersants may also be included and used, as long as the dispersant can ensure long-term storage stability without reacting with the polyolefin binder having an acid anhydride unit.

[0045] The curable composition according to the present application may include a polyolefin binder having an acid anhydride unit. The acid anhydride unit may be a maleic anhydride unit or a phthalic anhydride unit, among which the maleic anhydride unit is preferred. In addition, the acid anhydride unit may be bonded to the main chain of the polyolefin binder, or may be bonded to a substituent or a side chain of the polyolefin binder.

[0046] The acid value of the polyolefin binder may be 50 mg KOH / g or more, 55 mg KOH / g or more, 60 mg KOH / g or more, 65 mg KOH / g or more, or 70 mg KOH / g or more, and in another example, the acid value of the polyolefin binder may be 120 mg KOH / g or less, 110 mg KOH / g or less, 100 mg KOH / g or less, or 90 mg KOH / g or less. The acid value of the polyolefin binder may be a value measured according to the DIN EN ISO 2114 standard. From the acid value, the amount of the acid anhydride unit contained in the polyolefin binder can be known.

[0047] The polyolefin binder may include one or more units selected from a styrene unit, a butadiene unit, and an isoprene unit. Preferably, the polyolefin binder includes a butadiene unit.

[0048] The weight average molecular weight of the polyolefin binder may be 3,000 g / mol or more, 4,000 g / mol or more, 5,000 g / mol or more, 6,000 g / mol or more, 7,000 g / mol or more, 8,000 g / mol or more, 9,000 g / mol or more, or 10,000 g / mol or more, and in another example, the weight average molecular weight of the polymer compound containing the unit of Formula 1 above may be 30,000 g / mol or less, 25,000 g / mol or less, 20,000 g / mol or less, or 15,000 g / mol or less. The weight average molecular weight can be measured using GPC (gel permeation chromatography).

[0049] In addition, the number average molecular weight of the polyolefin binder may be 500 g / mol or more, 1,000 g / mol or more, 1,500 g / mol or more, 2,000 g / mol or more, 2,500 g / mol or more, or 3,000 g / mol or more, and in another example, the number average molecular weight of the polyolefin binder may be 6,000 g / mol or less, 5,500 g / mol or less, 5,000 g / mol or less, 4,500 g / mol or less, 4,000 g / mol or less, or 3,500 g / mol or less. The number average molecular weight can also be measured using GPC.

[0050] In addition, the polydispersity index (PDI) of the polyolefin binder may be in the range of 2 to 5, preferably in the range of 2.75 to 3.75.

[0051] When the weight-average molecular weight, number-average molecular weight, and polydispersity index of the polyolefin binder satisfy the above ranges, even when an excessive amount of filler is included, an appropriate viscosity can be maintained before and after curing.

[0052] The content of the polyolefin binder may be 1,000 parts by weight or more, 1,200 parts by weight or more, 1,400 parts by weight or more, 1,600 parts by weight or more, 1,800 parts by weight or more, or 2,000 parts by weight or more, based on 100 parts by weight of the dispersant. In another example, the content of the polyolefin binder may be 3,200 parts by weight or less, 3,000 parts by weight or less, 2,800 parts by weight or less, 2,600 parts by weight or less, 2,400 parts by weight or less, or 2,200 parts by weight or less, based on 100 parts by weight of the dispersant. When the content of the polyolefin binder satisfies the above ranges, even when an excessive amount of filler is mixed, an appropriate viscosity and long-term storage stability can be ensured.

[0053] The curable composition according to the present application may be included in a one-component composition or in the curing agent part of a two-component composition.

[0054] The curable composition according to the present application may be mixed with the main part to form a two-component composition. At this time, in the main part, a compound containing two or more hydroxyl groups may be included.

[0055] The curable composition according to the present application may include a filler to ensure the thermal conductivity of its cured product. At this time, the filler may be a thermal conductive filler.

[0056] The term thermal conductivity may refer to a case where, when the curable composition is mixed with the main part to form a two-component composition, and then a disc-shaped sample (cured product) with a diameter of 2 cm or more and a thickness of 500 μm is prepared using the two-component composition, the thermal conductivity is measured along the thickness direction of the sample according to ASTM D5470 standard or ISO 22007-2 standard, and shows a thermal conductivity of about 1.2 W / m·K or more.

[0057] In another example, the thermal conductivity can also be, for example, above about 1.3 W / m·K, above 1.4 W / m·K, above 1.5 W / m·K, above 1.6 W / m·K, above 1.7 W / m·K, above 1.8 W / m·K, above 1.9 W / m·K, above 2.0 W / m·K, above 2.1 W / m·K, above 2.2 W / m·K, above 2.3 W / m·K, above 2.4 W / m·K, above 2.5 W / m·K, above 2.6 W / m·K, above 2.7 W / m·K, above 2.8 W / m·K, above 2.9 W / m·K, or above 3.0 W / m·K. As the value of the thermal conductivity is higher, it indicates higher thermal conductivity, so there is no particular limitation on its upper limit. For example, the thermal conductivity can be below 20 W / m·K, below 18 W / m·K, below 16 W / m·K, below 14 W / m·K, below 12 W / m·K, below 10 W / m·K, below 8 W / m·K, below 6 W / m·K, or below 4 W / m·K.

[0058] The thermal conductivity of the thermal conductive filler itself can be, for example, above about 1 W / m·K, above about 5 W / m·K, above about 10 W / m·K, or above about 15 W / m·K. In another example, the thermal conductivity of the thermal conductive filler itself can be, for example, below about 400 W / m·K, below about 350 W / m·K, or below about 300 W / m·K.

[0059] The thermal conductive filler can be, for example, oxides such as aluminum oxide (alumina), magnesium oxide, beryllium oxide, or titanium oxide; nitrides such as boron nitride, silicon nitride, or aluminum nitride; and carbides such as silicon carbide; hydrated metals such as aluminum hydroxide or magnesium hydroxide; metal fillers such as copper, silver, iron, aluminum, or nickel; metal alloy fillers such as titanium; silicon powders such as quartz, glass, or silica, but not limited thereto.

[0060] In addition, if the insulation performance can be ensured, carbon fillers such as graphite can also be considered. For example, activated carbon can be used as the carbon filler. There is no particular limitation on the form or proportion of the filler contained in the cured product, and it can be selected considering the viscosity of the curable composition, the possibility of sedimentation in the cured product, the desired heat resistance or thermal conductivity, insulation, filling effect, or dispersibility, etc.

[0061] The shape of the thermal conductive filler can be appropriately selected and used from spherical and / or non-spherical (such as needle-shaped and plate-shaped, etc.) as needed, but not limited thereto.

[0062] As the heat conductive filler, one or two or more kinds appropriately selected according to need can be used. In addition, even when using the same type of heat conductive filler, heat conductive fillers having different shapes can be mixed and used, or heat conductive fillers having different average particle diameters can be mixed and used. For example, aluminum hydroxide, aluminum, and aluminum oxide can be mixed and used as the heat conductive filler, and their shapes and average particle diameters can be different from each other.

[0063] In addition, considering the amount to be filled, it is advantageous to use spherical heat conductive fillers, but heat conductive fillers in the form of needles or plates can also be used in view of network formation or conductivity.

[0064] In one example, the curable composition may contain a heat conductive filler having an average particle diameter in the range of 0.001 μm to 80 μm. In another example, the average particle diameter of the heat conductive filler may be 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 another example, the average particle diameter of the heat conductive filler may be about 75 μm or less, about 70 μm or less, about 65 μm or less, about 60 μm or less, about 55 μm or less, about 50 μm or less, about 45 μm or less, about 40 μm or less, about 35 μm or less, about 30 μm or less, about 25 μm or less, about 20 μm or less, about 15 μm or less, about 10 μm or less, or about 5 μm or less.

[0065] At this time, the average particle diameter of the heat conductive filler is the so-called D50 particle diameter (median particle diameter), which may refer to the particle diameter at the 50% cumulative volume of the particle size distribution. That is, the particle size distribution is obtained based on volume, and the particle diameter at the point where the cumulative value is 50% on the cumulative curve with a total volume of 100% can be regarded as the average particle diameter. This D50 particle diameter can be measured by the laser diffraction method.

[0066] According to the size of the heat-conductive filler, it can be classified into large heat-conductive filler, medium heat-conductive filler, and small heat-conductive filler. The average particle size of the large heat-conductive filler can be 80 μm or less, 78 μm or less, 76 μm or less, 74 μm or less, or 72 μm or less. In another example, the average particle size of the large heat-conductive filler can be 60 μm or more, 62 μm or more, 64 μm or more, 66 μm or more, or 68 μm or more. The average particle size of the medium heat-conductive filler can be 58 μm or less, 50 μm or less, 40 μm or less, or 25 μm or less. In another example, the average particle size of the medium heat-conductive filler can be 10 μm or more, 12.5 μm or more, 15 μm or more, or 17.5 μm or more. The average particle size of the small heat-conductive filler can be 9 μm or less, 5 μm or less, 3 μm or less, or 1 μm or less. In another example, the average particle size of the small heat-conductive filler can be 0.001 μm or more, 0.01 μm or more, 0.05 μm or more, 0.1 μm or more, 0.2 μm or more, 0.4 μm or more, 0.8 μm or more, or 1 μm or more.

[0067] As the heat-conductive filler, two or more of the large heat-conductive filler, medium heat-conductive filler, and small heat-conductive filler can be selected and used. At this time, the heat-conductive filler can satisfy the content ratio and / or particle size ratio within the following range, so that room-temperature rapid curability can be ensured through an appropriate combination with the polyolefin binder having an acid anhydride unit contained in the curable composition of the present application.

[0068] When the heat-conductive filler contains the large heat-conductive filler, the content of the large heat-conductive filler can be 30 wt% or more, 37.5 wt% or more, 42.5 wt% or more, 47.5 wt% or more, 50 wt% or more, 52.5 wt% or more, 55 wt% or more, 57.5 wt% or more, 60 wt% or more, or 62 wt% or more based on the total weight of the heat-conductive filler. In another example, the content of the large heat-conductive filler can be 87.5 wt% or less, 80 wt% or less, 75 wt% or less, 72.5 wt% or less, 70 wt% or less, 67.5 wt% or less, or 65 wt% or less based on the total weight of the heat-conductive filler. In addition, preferably, the large heat-conductive filler is spherical particles.

[0069] When the heat-conductive filler contains medium heat-conductive filler, relative to the total weight of the heat-conductive filler, the content of the medium heat-conductive filler can be 5% by weight or more, 10% by weight or more, 12% by weight or more, 14% by weight or more, 16% by weight or more, 18% by weight or more, or 20% by weight or more. In another example, relative to the total weight of the heat-conductive filler, the content of the medium heat-conductive filler can be 52.5% by weight or less, 50% by weight or less, 45% by weight or less, 40% by weight or less, 36% by weight or less, 32% by weight or less, 28% by weight or less, 24% by weight or less, or 20% by weight or less. Further, preferably, the medium heat-conductive filler is spherical particles.

[0070] When the heat-conductive filler contains small heat-conductive filler, relative to the total weight of the heat-conductive filler, the content of the small heat-conductive filler can be 5% by weight or more, 7.5% by weight or more, 10% by weight or more, 12.5% by weight or more, or 15% by weight or more. In another example, relative to the total weight of the heat-conductive filler, the content of the small heat-conductive filler can be 47.5% by weight or less, 40% by weight or less, 32.5% by weight or less, 25% by weight or less, 20% by weight or less, or 17.5% by weight or less. Further, preferably, the small heat-conductive filler is non-spherical particles.

[0071] When the heat-conductive filler contains large heat-conductive filler and medium heat-conductive filler, considering the room-temperature rapid curability of the curable composition according to the present application, preferably, relative to 100 parts by weight of the large heat-conductive filler, the content of the medium heat-conductive filler is 25 parts by weight or more, 26 parts by weight or more, 27 parts by weight or more, 28 parts by weight or more, 29 parts by weight or more, or 30 parts by weight or more. In another example, considering the room-temperature rapid curability of the curable composition according to the present application, preferably, relative to 100 parts by weight of the large heat-conductive filler, the content of the medium heat-conductive filler is 45 parts by weight or less, 42.5 parts by weight or less, 40 parts by weight or less, 37.5 parts by weight or less, 35 parts by weight or less, or 32.5 parts by weight or less. Further, preferably, the value of the average particle diameter (D1) of the large heat-conductive filler / the average particle diameter (D2) of the medium heat-conductive filler is 2 or more, 2.25 or more, 2.5 or more, 2.75 or more, 3 or more, 3.25 or more, or 3.5 or more, and preferably, is 5 or less, 4.5 or less, 4.25 or less, 4 or less, 3.75 or less, or 3.5 or less. When the large heat-conductive filler and the medium heat-conductive filler satisfy the above ranges, the room-temperature rapid curability of the curable composition according to the present application can be ensured.

[0072] When the heat-conductive filler contains large heat-conductive fillers and small heat-conductive fillers, considering the room-temperature rapid curability of the curable composition according to the present application, preferably, relative to 100 parts by weight of the large heat-conductive filler, the content of the small heat-conductive filler is 15 parts by weight or more, 17.5 parts by weight or more, 20 parts by weight or more, or 22.5 parts by weight or more. In another example, considering the room-temperature rapid curability of the curable composition according to the present application, preferably, relative to 100 parts by weight of the large heat-conductive filler, the content of the small heat-conductive filler is 40 parts by weight or less, 35 parts by weight or less, 30 parts by weight or less, or 25 parts by weight or less. Further, preferably, the value of the average particle size (D1) of the large heat-conductive filler / the average particle size (D3) of the small heat-conductive filler is 50 or more, 52.5 or more, 55 or more, 57.5 or more, 60 or more, 62.5 or more, 65 or more, 67.5 or more, or 70 or more, and preferably, it is 500 or less, 100 or less, 90 or less, 85 or less, 80 or less, 75 or less, or 70 or less. When the large heat-conductive filler and the small heat-conductive filler satisfy the above ranges, the room-temperature rapid curability of the curable composition according to the present application can be ensured.

[0073] In the present application, it is most preferable to use a heat-conductive filler containing all of the large heat-conductive filler, the medium heat-conductive filler, and the small heat-conductive filler. At this time, the content ratio and average particle size of each particle are as described above, and through their proper combination with the polyolefin binder having an acid anhydride unit, the room-temperature rapid curability of the curable composition according to the present application can be ensured.

[0074] As the heat-conductive filler, a heat-conductive filler having a Mohs hardness of 6 or more can be used. Considering the acrylic monomer component contained in the curable composition according to the present application and the desired thermal conductivity, preferably, relative to the total weight of the heat-conductive filler, the content of the heat-conductive filler having a Mohs hardness of 6 or more is 70% by weight or more, 75% by weight or more, or 80% by weight or more. In another example, preferably, relative to the total weight of the heat-conductive filler, the content of the heat-conductive filler having a Mohs hardness of 6 or more is 92.5% by weight or less, 90% by weight or less, 87.5% by weight or less, or 85% by weight or less.

[0075] However, although the heat-conductive filler having a Mohs hardness of 6 or more has favorable physical properties in terms of heat conduction, it may cause damage to the equipment due to its high surface hardness. Therefore, in order to prevent this problem, the heat-conductive filler can be used by additionally mixing a heat-conductive filler having a Mohs hardness of less than 6.

[0076] However, compared with the heat-conductive filler having a Mohs hardness of 6 or more, the heat-conductive filler having a Mohs hardness of less than 6 has unfavorable physical properties in terms of heat conduction. Therefore, by properly mixing these, while achieving the desired thermal conductivity, the hardness can be reduced, and equipment damage can be prevented.

[0077] In view of this aspect, with respect to 100 parts by weight of a heat conductive filler having a Mohs hardness of 6 or more, the content of a heat conductive filler having a Mohs hardness of less than 6 can be 5 parts by weight or more, 7.5 parts by weight or more, 10 parts by weight or more, 12.5 parts by weight or more, or 15 parts by weight or more, and in another example, can be 30 parts by weight or less, 25 parts by weight or less, 22.5 parts by weight or less, or 20 parts by weight or less.

[0078] Examples of the heat conductive filler having a Mohs hardness of 6 or more include, but are not particularly limited to, aluminum oxide (alumina), etc. In addition, examples of the heat conductive filler having a Mohs hardness of less than 6 include, but are not particularly limited to, aluminum hydroxide, etc.

[0079] Furthermore, the Mohs hardness of the heat conductive filler having a Mohs hardness of 6 or more can be 7 or more, 8 or more, or 9 or more, and the Mohs hardness of the heat conductive filler having a Mohs hardness of less than 6 can be 5 or less, 4 or less, or 3 or less.

[0080] The heat conductive filler may include spherical and non-spherical particles. In the present application, the term "spherical particles" refers to particles having a sphericity of about 0.95 or more, and non-spherical particles refer to particles having a sphericity of less than 0.95. The sphericity can be confirmed by particle shape analysis of the particles. Specifically, the sphericity of a filler as a three-dimensional particle can be defined as the ratio (S' / S) of the surface area (S') of a sphere having the same volume as the particle to the surface area (S) of the particle. For actual particles, roundness is usually used. Roundness is expressed as the ratio of the boundary of a circle having the same image and the same area (A) as the two-dimensional image of the actual particle obtained therefrom to the boundary (P) of the image, and is obtained from the following equation.

[0081] <Roundness equation>

[0082] Roundness = 4πA / P 2

[0083] Roundness is expressed as a value between 0 and 1, where the value of a perfect circle is 1, and since the particles have an irregular shape, the value is less than 1. The sphericity value in this specification is measured as the average value of roundness measured using a particle shape analysis device (FPIA-3000) of Marvern.

[0084] In view of the appropriate viscosity and thixotropy of the curable composition according to the present application, with respect to 100 parts by weight of spherical particles, the content of non-spherical particles can be 5 parts by weight or more, 7.5 parts by weight or more, 10 parts by weight or more, 12.5 parts by weight or more, or 15 parts by weight or more, and in another example, can be 30 parts by weight or less, 25 parts by weight or less, 22.5 parts by weight or less, or 20 parts by weight or less.

[0085] With respect to 100 parts by weight of the dispersant, the content of the filler can be 25,000 parts by weight or more, 26,000 parts by weight or more, 27,000 parts by weight or more, 28,000 parts by weight or more, 29,000 parts by weight or more, 30,000 parts by weight or more, 31,000 parts by weight or more, 32,000 parts by weight or more, or 33,000 parts by weight or more. In another example, with respect to 100 parts by weight of the dispersant, the content of the filler can be 45,000 parts by weight or less, 43,000 parts by weight or less, 41,000 parts by weight or less, 39,000 parts by weight or less, 37,000 parts by weight or less, 36,000 parts by weight or less, 35,000 parts by weight or less, or 34,000 parts by weight or less. When the content of the filler satisfies the above range, sedimentation of particles can be prevented even during long-term storage, and appropriate viscosity and thixotropy can be achieved. In addition, a cured product having excellent thermal conductivity can be formed.

[0086] In addition, the curable composition according to the present application may further contain a thiol compound to adjust the viscosity. There is no particular limitation on the thiol compound as long as it is a compound having a thiol group, but a thiol substituted with an alkyl group is preferred. Further, in consideration of the ease of operation with the polyolefin binder having an acid anhydride unit, the thiol compound is more preferably a thiol substituted with an alkyl group having 2 to 16 carbon atoms, an alkyl group having 4 to 14 carbon atoms, or an alkyl group having 8 to 12 carbon atoms.

[0087] In addition, in consideration of the combination with the dispersant containing an ester compound, with respect to 100 parts by weight of the dispersant, the content of the thiol compound can be 100 parts by weight or more, 125 parts by weight or more, 150 parts by weight or more, 175 parts by weight or more, 200 parts by weight or more, 225 parts by weight or more, 250 parts by weight or more, 275 parts by weight or more, or 300 parts by weight or more. In another example, with respect to 100 parts by weight of the dispersant, the content of the thiol compound can be 500 parts by weight or less, 475 parts by weight or less, 450 parts by weight or less, 425 parts by weight or less, 400 parts by weight or less, 375 parts by weight or less, 350 parts by weight or less, or 325 parts by weight or less. When the content of the thiol compound satisfies the above range, better long-term storage stability can be ensured.

[0088] If needed, the curable composition according to the present application may further comprise a plasticizer. A plasticizer is an additive that reduces the viscosity or plasticity of a material, and it may include phthalate series, trimellitate series, epoxy series, polyester series, etc. Phthalate plasticizers include, for example, DEHP (di(2-ethylhexyl) phthalate), DINP (diisononyl phthalate), DIDP (diisodecyl phthalate), etc., trimellitate plasticizers include, for example, TOTM (tris(2-ethylhexyl) trimellitate), etc. In addition, polyester plasticizers include, for example, DINA (diisononyl adipate), etc., and epoxy plasticizers include, for example, epoxy soybean oil (ESBO), etc. In addition, besides the above substances, the plasticizer may be an alkyl sulfonate of phenol (CAS No: 70775-94-9), and polyvinyl acetate for use in emulsions as a general adhesive, etc., but is not limited thereto.

[0089] If needed, the curable composition according to the present application may further comprise a flame retardant or a flame retardant aid. The curable composition further comprising 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 can be used without particular limitation. For example, a flame retardant in the form of a solid filler or a liquid flame retardant can be used. The flame retardant includes, for example, organic flame retardants such as melamine cyanurate, or inorganic flame retardants such as magnesium hydroxide, but is not limited thereto. When the amount of the heat-conducting filler contained in the curable composition is large, a liquid-type flame retardant material (such as TEP, i.e., triethyl phosphate, or TCPP, i.e., tris(1,3-dichloro-2-propyl) phosphate, etc.) can also be used. In addition, a silane coupling agent that can act as a flame retardant synergist can also be added.

[0090] The curable composition according to the present application may comprise the above composition, and may also be a solvent-based composition, an aqueous composition or a solvent-free composition.

[0091] The pressing force defined by the following Test 1 for the curable composition according to the present application may be 60 gf or less, 59 gf or less, 58 gf or less, 57 gf or less, 56 gf or less, 55 gf or less, 54 gf or less, 53 gf or less, 52 gf or less, 51 gf or less, 50 gf or less, 49 gf or less, or 48 gf or less. When the pressing force is greater than 60 gf, it can be evaluated that the dispersibility of the curable composition is reduced, and thus the particles settle.

[0092] [Test 1]

[0093] 1) After forming a curable composition containing a polyolefin binder having an acid anhydride unit, a filler, and a dispersant, immediately place it in a reactor and leave it at room temperature for 30 days or more.

[0094] 2) Inject the tip of the pressure measuring device into the point two-thirds of the curable composition placed in 1) above at a constant speed.

[0095] 3) Among the forces measured in 2) above, define the maximum force as the pressure.

[0096] In 1) of the above Test 1, the placement time can be 30 days or more, 40 days or more, 50 days or more, or 60 days or more.

[0097] Here, the room temperature is the natural temperature without heating or cooling, and refers to the temperature in the range of about 15°C to 30°C, 20°C to 28°C, or 24°C to 26°C.

[0098] In 1) above, the reactor can be in the form of a glass vial, where the glass vial can have a diameter of about 3 cm and a height of about 10 cm.

[0099] In addition, in 2) of the above Test 1, there is no particular limitation on the pressure measuring device, as long as it has a detachable tip and can measure the force exerted by the liquid material in contact with the tip. It can be exemplified as a Texture analyzer (TA), etc.

[0100] The curable composition according to the present application comprises: a polyolefin binder having an anhydride unit; a filler; and a phosphoric acid-based polymer dispersant, where the pressure can be 60 gf or less. Here, the polyolefin binder having an anhydride unit and the filler are the same as above. In addition, the phosphoric acid-based polymer dispersant can include a polymer compound containing the unit of Formula 1 as described above. In addition, for the pressure, the pressure defined by the above Test 1 can be 60 gf or less, 59 gf or less, 58 gf or less, 57 gf or less, 56 gf or less, 55 gf or less, 54 gf or less, 53 gf or less, 52 gf or less, 51 gf or less, 50 gf or less, 49 gf or less, or 48 gf or less.

[0101] The curable composition can be cured according to the above method to form a cured product, and can have at least one or more of the following physical properties. Each of the physical properties described below is independent, where any one physical property is not superior to other properties, and the cured product of the curable composition can satisfy at least one or two or more of the following physical properties. That the cured product of the curable composition satisfies at least one or two or more of the following physical properties is caused by the combination of each component in the curable composition.

[0102] In addition, the curable composition may be included in the curing agent part of a two-component composition. That is, the curable composition according to the present application may be mixed with the main part to form a two-component composition. At this time, in the main part, a compound containing two or more hydroxyl groups may be included. The physical properties described below may each be for the cured product in which the two-component composition is cured.

[0103] The thermal resistance of the cured product may be about 5 K / W or less, about 4.5 K / W or less, about 4 K / W or less, about 3.5 K / W or less, about 3 K / W or less, or about 2.8 K / W or less. When adjusted so that the thermal resistance within the above range can be exhibited, excellent cooling efficiency or heat dissipation efficiency can be ensured. The thermal resistance may be a value measured according to the ASTM D5470 standard or the ISO 22007-2 standard, and there is no particular limitation on the measurement method.

[0104] In addition, the adhesion force may be the adhesion force to any substrate or module housing in contact with the cured product. If such adhesion force can be ensured, appropriate adhesion force can be exhibited to various materials, for example, the housing or battery cells included in the battery module, etc. In addition, if the adhesion force within the above range is ensured, peeling, etc. caused by volume change, change in the use temperature of the battery module, or curing shrinkage, etc. during the charging and discharging process of the battery cells in the battery module can be prevented. Thus, excellent durability can be ensured. In addition, reprocessability that enables the module to be disassembled and reattached during the assembly process of the battery pack can be ensured.

[0105] The cured product can ensure durability so as to be applied to products that require a long warranty period, such as automobiles (in the case of automobiles, more than about 15 years). Durability may mean that after a thermal shock test in which the process of maintaining the temperature at about -40°C for 30 minutes and then raising the temperature to 80°C and maintaining it for 30 minutes is set as one cycle and this cycle is repeated 100 times, there will be no separation, peeling, or cracking from the module housing or battery cells of the battery module.

[0106] The electrical insulation of the cured product can be about 3 kV / mm or more, about 5 kV / mm or more, about 7 kV / mm or more, 10 kV / mm or more, 15 kV / mm or more, or 20 kV / mm or more. Since the dielectric breakdown voltage has a higher value, the cured product exhibits excellent insulation properties, which can be about 50 kV / mm or less, 45 kV / mm or less, 40 kV / mm or less, 35 kV / mm or less, or 30 kV / mm or less, but there is no particular limitation. To achieve such a dielectric breakdown voltage, an insulating filler can be added to the curable composition. Generally, among thermal conductive fillers, ceramic fillers are known components that can ensure insulation properties. The electrical insulation can be measured using the dielectric breakdown voltage measured according to ASTM D149 standard. In addition, if the cured product can ensure electrical insulation as described above, stability can be ensured while maintaining performance for various materials, such as the housing or battery cells included in the battery module, etc.

[0107] The specific gravity of the cured product can be 5 or less. In another example, the specific gravity can be 4.5 or less, 4 or less, 3.5 or less, or 3 or less. As the specific gravity of the cured product has a lower value, it is more beneficial for the weight reduction of the applied product. Therefore, there is no particular limitation on its lower limit. For example, the specific gravity can be about 1.5 or more, or 2 or more. To make the cured product exhibit such a specific gravity, for example, a method of applying the following fillers can be used, which can ensure the desired thermal conductivity even at a low specific gravity when adding thermal conductive fillers, that is, fillers with a low specific gravity themselves, or applying surface-treated fillers, etc.

[0108] As needed, it is appropriate that the cured product does not contain volatile materials. For example, in the cured product, the proportion of non-volatile components can be 90 wt% or more, 95 wt% or more, or 98 wt% or more. Here, the proportion of non-volatile components can be defined in the following way. That is, for the non-volatile content, the remaining part after keeping the cured product at 100 °C for about 1 hour can be defined as the non-volatile content. Therefore, the proportion can be measured based on the proportion after keeping at 100 °C for about 1 hour and the initial weight of the cured product.

[0109] As needed, the cured product can have excellent anti-degradation properties, where, as needed, stability without chemical reaction may be required.

[0110] It would be advantageous for the cured product to have a low shrinkage rate during or after curing. Thereby, it is possible to prevent the occurrence of peeling or voids or the like that may occur during the manufacture or use of various materials, for example, the housing or battery cells included in a battery module. The shrinkage rate can be appropriately adjusted within a range capable of exhibiting the above effects. For example, it can be less than 5%, less than 3%, or less than about 1%. Since the lower the value, the more advantageous the shrinkage rate, there is no particular limitation on its lower limit.

[0111] The cured product may also advantageously have a low coefficient of thermal expansion (CTE). Thereby, it is possible to prevent the occurrence of peeling or voids or the like that may occur during the manufacture or use of various materials, for example, the housing or battery cells included in a battery module. The coefficient of thermal expansion can be appropriately adjusted within a range capable of exhibiting the above effects. For example, it can be 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, the more advantageous the coefficient of thermal expansion, there is no particular limitation on its lower limit.

[0112] In the cured product, the tensile strength can be appropriately adjusted, whereby excellent impact resistance and the like can be ensured. The tensile strength can be adjusted, for example, within a range of about 1.0 MPa or more.

[0113] In the cured product, the elongation at break can be appropriately adjusted, whereby excellent impact resistance can be ensured. The elongation at break can be adjusted, for example, within a range of about 10% or more or about 15% or more.

[0114] It would be advantageous for the cured product to also exhibit appropriate hardness. The term "appropriate hardness" can be a hardness at which the cured product is not evaluated as brittle. When the hardness of the cured product is too high, the cured product is too brittle, which will adversely affect the reliability. In addition, by adjusting the hardness, impact resistance and vibration resistance can be ensured, and the durability of the product can be ensured. In the cured product, the hardness can be measured using a hardness scale. In addition, for example, the Shore 00 hardness of the cured product can be less than about 80. The hardness of the cured product generally depends on the type or proportion of the filler contained in the cured product, and when an excessive amount of filler is contained, the hardness generally increases.

[0115] In the cured product, the temperature at 5% weight loss in thermogravimetric analysis (TGA) can also be 400 °C or higher, or the residue amount at 800 °C can be 70% by weight or higher. Due to these characteristics, for various materials, such as the outer casing or battery cells included in a battery module, etc., the high-temperature stability can be further improved. In another example, the residue amount at 800 °C can 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 another example, the residue amount at 800 °C can be about 99% by weight or less. Thermogravimetric analysis (TGA) can be measured in a nitrogen (N2) atmosphere at 60 cm 3 / min at a heating rate of 20 °C / min in the range of 25 °C to 800 °C. The results of thermogravimetric analysis (TGA) can also be obtained by adjusting the composition of the cured product. For example, the residue amount at 800 °C depends on the type or proportion of the thermally conductive filler contained in the cured product, and when an excessive amount of the thermally conductive filler is included, the residue amount increases. However, when the polymers and / or monomers used in the curable composition generally have high heat resistance compared to other polymers and / or monomers, the residue amount increases more, and the polymer and / or monomer components contained in the cured product also affect the hardness.

[0116] The curable composition of the present application can be formed by stirring and mixing a polyolefin binder having an acid anhydride unit, a filler, and a dispersant. In addition, the curable composition can be formed by adding a polyolefin binder having an acid anhydride unit, a filler, and a dispersant, adding a plasticizer and a flame retardant, etc., and then stirring and mixing them.

[0117] The curable composition of the present application has no particular limitation on the mixing order as long as all necessary components can be included.

[0118] The curable composition of the present application can be used in various electrical and electronic products, such as irons, washing machines, dryers, clothes managers, electric shavers, microwave ovens, electric ovens, rice cookers, refrigerators, dishwashers, air conditioners, fans, humidifiers, air purifiers, mobile phones, radiotelegraphs, televisions, radios, computers, and laptops, or batteries such as secondary batteries, to dissipate the generated heat. In particular, in a battery for an electric vehicle manufactured by aggregating battery cells to form a battery module and combining several battery modules to form a battery pack, the curable composition of the present application can be used as a material for connecting the battery modules. When the curable composition of the present application is used as a material for connecting the battery modules, it can play a role in dissipating the heat generated in the battery cells and fixing the battery cells from the effects of external shocks and vibrations.

[0119] The present application can provide a device including a heat - generating element and a cooling area, wherein the device includes a cured product of the curable composition of the present application that is in thermal contact with both between the heat - generating element and the cooling area.

[0120] The device can be various electrical and electronic products, such as irons, washing machines, dryers, clothing managers, electric shavers, microwave ovens, electric ovens, rice cookers, refrigerators, dishwashers, air conditioners, fans, humidifiers, air purifiers, mobile phones, radiotelegraphs, televisions, radios, computers and laptops or batteries (such as battery cells and battery modules, etc.) like secondary batteries.

[0121] The cured product of the curable composition of the present application can transfer the heat generated by the heat - generating element to the cooling area. That is, the cured product of the curable composition can dissipate the heat generated by the heat - generating element.

[0122] The cured product of the curable composition can be located between the heat - generating element and the cooling area to be in thermal contact with them. Thermal contact means that the cured product of the curable composition is physically in direct contact with the heat - generating element and the cooling area to dissipate the heat generated by the heat - generating element to the cooling area, or even if the cured product of the curable composition is not in direct contact with the heat - generating element and / or the cooling area (i.e., there is a separate layer between the cured product of the curable composition and the heat - generating element and / or the cooling area), it can still dissipate the heat generated by the heat - generating element to the cooling area.

[0123] Advantageous Effects

[0124] The present application can provide a curable composition that has appropriate viscosity and thixotropy before and after curing even when containing an excessive amount of filler.

[0125] The present application can provide a curable composition that has no particle sedimentation phenomenon even during long - term storage. Description of the Drawings

[0126] Figure 1 is a graph showing the forces measured over time for the curable compositions according to Example 1 and Example 2 and Comparative Examples 1 to 4 of the present application. Detailed Description

[0127] Hereinafter, the present application will be described through examples and comparative examples, but the scope of the present application is not limited by the content provided below.

[0128] <Method for Measuring Physical Properties>

[0129] (1) Evaluation Method for Long - Term Particle Sedimentation

[0130] The curable composition was placed in a glass vial and left at room temperature and atmospheric pressure for about 60 days. After that, the curable composition in the glass vial was visually observed, and the particle sedimentation was evaluated according to the following criteria.

[0131] PASS: In the vial, the curable composition remained in its liquid form without phase separation.

[0132] NG: In the vial, phase separation of the curable composition occurred or the curable composition hardened due to curing.

[0133] (2) Method for measuring pressure

[0134] The formed curable composition was placed at a height of 30 mm from the bottom of a glass vial (with a diameter of about 3 cm and a height of about 10 cm) and left at room temperature for about 60 days.

[0135] To measure the pressure, a tip detachable from a Texture Analyzer (TA) was fabricated. Specifically, the tip was a tip with a total height of 4 cm formed by joining a cylinder (T1 part) with a diameter of 1 mm and a height of 1 cm and a cylinder (T3 part) with a diameter of 3 mm and a height of 3 cm. The end of the T3 part was connected to the Texture Analyzer. After that, the glass vial containing the placed curable composition was placed in the measurement space of the Texture Analyzer, and the end of the T1 part was placed facing the curable composition contained in the glass vial at a distance of 5 mm, thus completing the pressure measurement setup.

[0136] After that, the force applied to the tip was measured by pressing the curable composition contained in the glass vial while lowering the tip at a constant speed of 2 mm / s. At this time, the force and pressure applied to the tip were measured over time from the moment the end of the T1 part came into contact with the curable composition until a depth of 20 mm was reached.

[0137] Example 1

[0138] A polybutadiene containing maleic anhydride units (A, manufacturer: Evonik, product name: polyvest MA75), a heat-conductive filler (B), and a dispersant (C) were mixed at a weight ratio of 100∶1,600∶4.8 (A∶B∶C) to form a curable composition.

[0139] As the polybutadiene (A) containing maleic anhydride units, one with an acid value of about 70 to 90 mg KOH / g (determined by DIN EN ISO 2114), a weight-average molecular weight (M w ) of about 10,200 g / mol, a number-average molecular weight (M n ) of about 3,060 g / mol, and a polydispersity index (PDI = Mw / M n ) is polybutadiene of about 3.32 or so.

[0140] In addition, as the heat conductive filler (B), a mixture of spherical alumina (B1) with an average particle size of about 70 μm, spherical alumina (B2) with an average particle size of about 20 μm, and non-spherical aluminum hydroxide (B3) with an average particle size of about 1 μm in a weight ratio of 65:20:15 (B1:B2:B3) is used.

[0141] The average particle size of the filler mentioned in this specification is the D50 particle size, also known as the so-called median particle size, which is the particle size (median particle size) at the 50% cumulative point of the cumulative curve of the volume-based particle size distribution. This particle size can be defined as the particle size obtained based on the volume to obtain the particle size distribution and at the cumulative value of 50% on the cumulative curve with respect to the total volume of 100%. The D50 particle size can be measured using a Marven MASTERSIZER 3000 device based on ISO-13320, where ethanol is used as the solvent.

[0142] As the dispersant (C), DISPERBYK-118 of BYK is used. The weight average molecular weight (M w ) is about 16,500 g / mol or so, and the polydispersity index (PDI = M w / M n ) is about 1.23 or so. In addition, in the dispersant, about 20% by weight based on the total weight is made of propylene glycol monomethyl ether acetate (propylene glycol monomethyl ether acetate), and the rest is made of a compound containing the unit of Formula 1, and the unit is a copolymer unit of polypropylene glycol (PPG), polyethylene glycol (PEG), and phosphoric acid (PA).

[0143] [Formula 1]

[0144]

[0145] In the above Formula 1, p / q is about 1.

[0146] Example 2

[0147] A curable composition is formed in the same manner as in Example 1 above, except that a polybutadiene (A, manufacturer: Evonik, product name: polyvest MA75) containing maleic anhydride units, a heat conductive filler (B), and a dispersant (C) are mixed in a weight ratio of 100:1,600:4.8 (A:B:C), and a thiol compound (D) is also mixed. As the thiol compound (D), 1-dodecanethiol is used, and the addition amount of the thiol compound (D) is 300 parts by weight relative to 100 parts by weight of the dispersant (C).

[0148] Comparative Example 1

[0149] The same polybutadiene (A, manufacturer: Evonik, product name: polyvest MA75) containing maleic anhydride units and the heat-conductive filler (B) as in Example 1 above were used, but they were mixed at a weight ratio of 100:1,600 (A:B) without using the dispersant (C) to form a curable composition.

[0150] Comparative Example 2

[0151] A curable composition was formed in the same manner as in Example 1 above, except that DISPERBYK-111 of the phosphoric acid-based dispersant BYK was used as the dispersant (C). The weight-average molecular weight (M w ) was about 1,750 g / mol, and the polydispersity index (PDI = M w / M n ) was about 1.7.

[0152] Comparative Example 3

[0153] A curable composition was formed in the same manner as in Example 1, except that DISPERBYK-102 of the phosphoric acid-based dispersant BYK was used as the dispersant (C). DISPERBYK-102 has a lower polarity than DISPERBYK-111 used in Comparative Example 2. The weight-average molecular weight (M w ) was about 1,630 g / mol, and the polydispersity index (PDI = M w / M n ) was about 1.46.

[0154] Comparative Example 4

[0155] A curable composition was formed in the same manner as in Example 1 above, except that polybutadiene (A, manufacturer: Evonik, product name: polyvest MA75) containing maleic anhydride units, the heat-conductive filler (B), and the thiol compound (D) were mixed at a weight ratio of 100:1,600:4.8 (A:B:D). As the thiol compound (D), 1-dodecanethiol was used.

[0156] The measurement results of the physical properties of the above Examples and Comparative Examples are shown in the following table.

[0157] [Table 1]

[0158] Category Long - term settlement evaluation Pressure (gf) Example 1 X 46.8 Example 2 X 27.7 Comparative Example 1 ○ 67.0 Comparative Example 2 ○ 219.7 Comparative Example 3 ○ 184.8 Comparative Example 4 ○ 65.9

[0159] As shown in Table 1, it can be seen that in the evaluation of long-term particle sedimentation, the curable compositions according to Example 1 and Example 2 did not sediment even after being left for a long time. Thus, it can be seen that the long-term storage stability is excellent.

[0160] On the other hand, in the evaluation of long-term particle sedimentation, the curable compositions according to Comparative Examples 1 to 4 caused layer separation by sedimenting the particles in the vial.

[0161] Here, as shown in Table 1, the pressure of the curable composition according to Example 1 was 46.8 gf, and the pressure of the curable composition according to Example 2 was 27.7 gf. It can be seen that neither of them caused particle sedimentation even when left for a long time.

[0162] On the other hand, the pressures of the curable compositions according to Comparative Examples 1 to 4 were 67.0 gf, 219.7 gf, 184.8 gf, and 65.9 gf, respectively, and it can be seen that all of them caused particle sedimentation when left for a long time.

[0163] Figure 1 is a graph showing the forces measured over time for the curable compositions according to Example 1 and Example 2 and Comparative Examples 1 to 4 of the present application. In Figure 1 the part where the pressure rapidly increases over time is the time when the T3 part at the fingertip contacts the curable composition.

[0164] As Figure 1 shown, it can be seen that the maximum forces of the curable compositions according to Example 1 and Example 2 and Comparative Examples 1 to 4 are as shown in Table 1 above.

[0165] In this document, the constitution and features of the present application have been described based on the examples of the present application. However, the present application is not limited thereto, and it is obvious to those skilled in the technical field to which the present application pertains that various changes or modifications can be made within the concept and scope of the present application. Therefore, it is pointed out that such changes or modifications fall within the scope of the appended claims.

Claims

1. A curable composition comprising a polyolefin binder having acid anhydride units; a filler; and a dispersant; wherein, The dispersant contains a polymer compound containing units of the following formula 1: [Formula 1] wherein, L1 is an alkylene group having 3 to 6 carbon atoms, L2 is a methylene group or an ethylene group, and p / q is a value in the range of 0.5 to 2.

2. The curable composition according to claim 1, wherein, The acid anhydride unit is a maleic anhydride unit or a phthalic anhydride unit.

3. The curable composition according to claim 1, wherein, The acid value of the polyolefin binder is in the range of 50 mg KOH / g to 120 mg KOH / g.

4. The curable composition according to claim 1, wherein, The polyolefin binder contains one or more units selected from a styrene unit, a butadiene unit, and an isoprene unit.

5. The curable composition according to claim 1, wherein, The weight-average molecular weight of the polyolefin binder is in the range of 3,000 g / mol to 30,000 g / mol.

6. The curable composition according to claim 1, wherein, The polydispersity index of the polyolefin binder is in the range of 2 to 5.

7. The curable composition according to claim 1, wherein, The weight-average molecular weight of the polymer compound containing units of formula 1 is in the range of 5,000 g / mol to 40,000 g / mol.

8. The curable composition according to claim 1, wherein, The polydispersity index of the polymer compound containing units of formula 1 is in the range of 0.8 to 2.

9. The curable composition according to claim 1, wherein, relative to 100 parts by weight of the polyolefin binder, the curable composition comprises 1 to 10 parts by weight of the dispersant.

10. The curable composition according to claim 1, wherein, The dispersant further contains an ester compound.

11. The curable composition according to claim 10, wherein, The ester compound includes one or more selected from alkylene glycol monoalkyl ether acetates, alkyl alkoxy propionates, alkylene glycol monoalkyl ether propionates, alkylene glycol diacetates, alkyl lactates, and 2-hydroxyisoalkyl acid alkyl esters.

12. The curable composition according to claim 1, further comprising a thiol compound.

13. The curable composition according to claim 12, wherein, The thiol compound is a thiol substituted with an alkyl group having 1 to 20 carbon atoms.

14. The curable composition according to claim 1, wherein, The filler is contained in a proportion of 25,000 parts by weight to 45,000 parts by weight relative to 100 parts by weight of the dispersant.

15. The curable composition according to claim 10, wherein, The dispersant contains the ester compound in an amount of 5 wt% to 40 wt%.

16. The curable composition according to claim 12, wherein, The thiol compound is contained in a proportion in the range of 100 parts by weight to 500 parts by weight relative to 100 parts by weight of the dispersant.

17. The curable composition according to claim 1, wherein, The pressure of the curable composition is 60 gf or less, wherein the pressure is defined by the following Test 1. [Test 1] 1) After forming a curable composition containing a polyolefin binder having an acid anhydride unit, a filler, and a dispersant, immediately put it into a reactor and leave it at room temperature for 30 days or more. 2) Inject the tip of the pressure measuring device into the 2 / 3 point of the curable composition placed in 1) above at a constant speed. 3) Among the forces measured in 2) above, define the maximum force as the pressure.

18. A curable composition comprising: a polyolefin binder having acid anhydride units; a filler; and a phosphoric acid-based polymer dispersant, wherein, The pressure of the curable composition is 60 gf or less. wherein the phosphoric acid-based polymer dispersant contains a polymer compound containing units of the following formula 1: [Formula 1] wherein, L1 is an alkylene group having 3 to 6 carbon atoms, L2 is a methylene group or an ethylene group, and p / q is a value in the range of 0.5 to 2. wherein the pressure is defined by the following Test 1. [Test 1] 1) After forming a curable composition containing a polyolefin binder having an acid anhydride unit, a filler, and a dispersant, immediately put it into a reactor and leave it at room temperature for 30 days or more. 2) Inject the tip of the pressure measuring device into the 2 / 3 point of the curable composition placed in 1) above at a constant speed. 3) Among the forces measured in 2) above, define the maximum force as the pressure.

19. A device comprising: an exothermic element; and a cooling region, wherein, The device comprises a cured product of the curable composition of claim 1 or the curable composition of claim 18 in thermal contact with both the exothermic element and the cooling zone therebetween.

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