Hardening composition

Abstract

The present invention provides a curable composition, a thermal interface material (TIM), and uses thereof. The curable composition or thermal interface material exhibits high thermal conductivity while exhibiting low adhesion to a specific substrate. The present invention also achieves the low adhesion without using or minimizing the use of an adhesion-adjusting component such as a plasticizer. The present invention also provides a curable composition that exhibits a precisely controlled curing rate and excellent curability. The present invention also provides a product comprising the curable composition, its cured product, or a thermal interface material.

Description

[Technical Field]

[0001] This application claims the benefit of priority based on Korean Patent Application No. 10-2022-0116474, filed September 15, 2022, and all contents disclosed in the documents of said Korean patent application are incorporated herein by reference.

[0002] The present invention relates to a curable composition, a thermal interface material (TIM), and uses thereof. [Background technology]

[0003] With the increase in electric or electronic devices that require heat management, such as batteries, the importance of heat dissipation materials such as TIM (Thermal Interface Material) is increasing. A wide variety of heat dissipation materials are known. One known conventional heat dissipation material is a material in which a resin binder is filled with a heat dissipation filler (for example, Patent Document 1).

[0004] In the heat dissipating material as described above, silicone resin, polyolefin resin, acrylic resin, epoxy resin, or the like is usually used as the resin binder.

[0005] A heat dissipation material is basically required to have excellent thermal conductivity, and additional functions are required depending on the application. For example, depending on the application, a heat dissipation material is required to have high thermal conductivity as well as low adhesive strength to a specific substrate.

[0006] For example, when it is necessary to replace a part that comes into contact with the heat dissipation material within a product, or when it is necessary to change the position of the heat dissipation material during a manufacturing process, the heat dissipation material must exhibit low adhesive strength.

[0007] Among known heat dissipation materials, materials that exhibit low adhesive strength include those that use silicone resin as a resin binder. However, silicone resin is relatively expensive. Furthermore, silicone resin contains components that can cause poor contact when applied to electronic / electrical products, limiting its applications.

[0008] The polyurethane material used in Patent Document 1 can be used to form a heat-dissipating material with high thermal conductivity and has a variety of other advantages, but it is also a material that exhibits high adhesive strength to many adherends.

[0009] One way to reduce the adhesive strength of a material that exhibits high adhesive strength is to incorporate a component known as a plasticizer. However, the use of a large amount of plasticizer to control adhesive strength can lead to problems such as impairing the inherent advantages of the material itself and leaching out during use.

[0010] For a heat-dissipating material that has a curing property, it is necessary to control the curing speed of the heat-dissipating material.

[0011] That is, when a heat dissipation material is formed using a curable heat dissipation material, the uncured heat dissipation material is applied to a desired location and then cured. However, even after applying the heat dissipation material, it may be necessary to replace components that come into contact with the heat dissipation material within the product or to change the position of the heat dissipation material and / or the component. However, if the heat dissipation material hardens rapidly, the viscosity and hardness of the material also increase rapidly, which may result in a very short time available for replacement or repositioning.

[0012] Furthermore, if the curing of the heat-dissipating material occurs too quickly, the time available for dispensing the material using a dispenser or injection device will also be shortened. Typically, the process of applying the heat-dissipating material involves a waiting period after loading the heat-dissipating material into the dispenser or injection device, but if the curing of the heat-dissipating material occurs too quickly, the waiting period cannot be adequately secured. [Prior art documents] [Patent documents]

[0013] [Patent Document 1] Korean Patent Publication No. 2016-0105354 Summary of the Invention [Problem to be solved by the invention]

[0014] The present invention provides a curable composition, a thermal interface material (TIM), and uses thereof. The thermal interface material may be formed by curing the curable composition. One object of the present invention is to provide the curable composition or thermal interface material, etc., with high thermal conductivity while exhibiting low adhesive strength to a predetermined substrate. Another object of the present invention is to achieve the low adhesive strength without using or minimizing the use of adhesive strength modifiers such as plasticizers.

[0015] Another object of the present invention is to provide a curable composition that exhibits a precisely controlled cure rate while at the same time possessing excellent curability.

[0016] Another object of the present invention is to provide a product comprising the curable composition, a cured product thereof, or a thermal interface material. [Means for solving the problem]

[0017] In the present specification, when the measurement temperature affects the results of physical properties, the physical properties are measured at room temperature unless otherwise specified. The term "room temperature" refers to a natural temperature that is neither heated nor cooled, and typically refers to a temperature within the range of about 10°C to 30°C, or a temperature of about 23°C or about 25°C. Furthermore, unless otherwise specified in the present specification, the unit of temperature is °C.

[0018] In the present specification, when the measurement pressure affects the physical properties, the physical properties are measured at atmospheric pressure unless otherwise specified. The term "atmospheric pressure" refers to the natural pressure without pressure increase or decrease, and generally refers to atmospheric pressure within the range of approximately 700 mmHg to 800 mmHg.

[0019] The present invention relates to a resin composition. The term "resin composition" refers to a composition containing a component known in the art as a resin, or a composition that does not contain a resin but contains a component that can form a resin through a curing reaction or the like. Therefore, the term "resin" or "resin component" as used herein includes not only components generally known as resins, but also components that can form a resin through a curing and / or polymerization reaction.

[0020] The resin composition may be a curable composition. The curable composition can be cured to form a thermal interface material (TIM). Therefore, in this specification, the cured product of the resin composition and the thermal interface material can refer to the same object.

[0021] When the resin composition of the present invention is a curable composition, the resin composition may be a one-component or two-component composition. The term "one-component composition" refers to a resin composition in which the components participating in curing are physically in contact with each other, and the term "two-component composition" refers to a resin composition in which at least some of the components participating in curing are physically separated.

[0022] When the resin composition of the present invention is a curable composition, the resin composition may be of a room temperature curable type, a heat curable type, an energy ray curable type, and / or a moisture curable type. The term "room temperature curable type" refers to a resin composition in which the curing reaction can be initiated and / or proceeded at room temperature, the term "heat curable type" refers to a resin composition in which the curing reaction can be initiated and / or proceeded by the application of heat, the term "energy ray curable type" refers to a resin composition in which the curing reaction can be initiated and / or proceeded by irradiation with energy rays (e.g., ultraviolet rays, electron beams, etc.), and the term "moisture curable type" refers to a resin composition in which the curing reaction can be initiated and / or proceeded in the presence of moisture.

[0023] The resin composition of the present invention may be a solvent-based or solventless type. In view of application efficiency and environmental load, the solvent-free type is preferable.

[0024] The resin composition of the present invention may be a polyurethane composition. In such a case, the resin composition may contain polyurethane or a component capable of forming polyurethane. For example, a thermal interface material that is a cured product of the resin composition may contain the polyurethane. In one example, the polyurethane can be formed by a reaction between a curable component described below and a curing agent for the curable component.

[0025] The resin composition of the present invention can exhibit low adhesion to a specific substrate or can form a cured product capable of exhibiting low adhesion. Such a resin composition may be the polyurethane composition described above. Polyurethanes are known as adhesive materials that exhibit excellent adhesion to a variety of substrates. Therefore, a common method for making a polyurethane composition exhibit low adhesion to a substrate is to incorporate a component that reduces adhesion, such as a plasticizer. While the addition of such a component can reduce the adhesive strength of the polyurethane material, it can also cause problems, such as reducing other physical properties that the polyurethane possesses or leaching out of the material during use. However, the present invention can achieve the low adhesive strength of a polyurethane material without using or minimizing the amount of an adhesive-reducing component, such as a plasticizer. Therefore, the present invention can provide a material that retains the advantages of polyurethane materials while addressing the problem of high adhesive strength, which is not required for certain applications.

[0026] The resin composition or its cured product has an adhesive strength to aluminum of 1 N / mm 2 In another example, the upper limit of the adhesive strength of the resin composition or the cured product thereof to aluminum may be 0.9 N / mm 2 , 0.8N / mm 2 , 0.7N / mm 2 , 0.6N / mm 2 , 0.5N / mm 2 , 0.4N / mm 2 , 0.3N / mm 2 , 0.2N / mm 2 , 0.1N / mm 2 , 0.15N / mm 2 , 0.09N / mm 2 , 0.08N / mm 2 , 0.07N / mm 2 , 0.06N / mm 2 , 0.04N / mm 2 or 0.03N / mm 2The adhesive strength of the resin composition or its cured product to aluminum may be equal to or less than any one of the upper limits described above. In the present invention, the lower limit of the adhesive strength to aluminum is not particularly limited. In one example, the adhesive strength to aluminum is 0 N / mm 2 or more or 0N / mm 2 The resin composition may be a resin composition in which the adhesive strength to aluminum is not substantially measurable, or may be a resin composition capable of forming a cured product in which the adhesive strength to aluminum is not substantially measurable. Therefore, the adhesive strength to aluminum is 0 N / mm 2 or more or 0N / mm 2 The adhesive strength of the resin composition or its cured product to aluminum can be measured by the method described in the Examples of this specification.

[0027] The resin composition or its cured product may have an adhesive strength to polyester of 100 gf / cm or less. In other examples, the upper limit of the adhesive strength of the resin composition or its cured product to polyester may be 95 gf / cm, 90 gf / cm, 85 gf / cm, 80 gf / cm, 75 gf / cm, 70 gf / cm, 65 gf / cm, 60 gf / cm, 55 gf / cm, 50 gf / cm, 45 gf / cm, 40 gf / cm, 35 gf / cm, 30 gf / cm, 25 gf / cm, or 20 gf / cm. The adhesive strength of the resin composition or its cured product to polyester may be equal to or less than any one of the upper limits mentioned above. In the present invention, the lower limit of the adhesive strength to polyester is not particularly limited. In one example, the lower limit of the adhesive strength of the resin composition or its cured product to the polyester may be approximately 0 gf / cm, 2 gf / cm, 4 gf / cm, 6 gf / cm, 8 gf / cm, 10 gf / cm, 12 gf / cm, 14 gf / cm, 16 gf / cm, 18 gf / cm, or 20 gf / cm. The resin composition or its cured product may exhibit substantially no adhesive strength to polyester. The adhesive strength of the resin composition or its cured product to polyester may be in a range between any one of the above lower limits and any one of the above upper limits. The adhesive strength of the resin composition or its cured product to polyester may be measured by the method described in the Examples of this specification.

[0028] The resin composition or its cured product can exhibit excellent thermal conductivity. For example, the lower limit of the thermal conductivity of the resin composition or its cured product may be approximately 1.2 W / mK, 1.4 W / mK, 1.6 W / mK, 1.8 W / mK, 2.0 W / mK, 2.2 W / mK, 2.4 W / mK, or 2.6 W / mK. The thermal conductivity may be equal to or greater than any one of the above-mentioned lower limits. There is no particular limit on the upper limit of the thermal conductivity. For example, the upper limit of the thermal conductivity of the resin composition or its cured product may be approximately 10 W / mK, 9 W / mK, 8 W / mK, 7 W / mK, 6 W / mK, 5 W / mK, 4 W / mK, or 3 W / mK. The thermal conductivity may be in a range between any one of the above-mentioned lower limits and any one of the above-mentioned upper limits. The thermal conductivity of such a resin composition or its cured product can be measured by the method disclosed in the Examples below.

[0029] The resin composition or its cured product may also exhibit an appropriate hardness. For example, if the hardness of the resin composition or its cured product is too high, it may become significantly brittle, which may cause problems. Furthermore, adjusting the hardness of the resin composition or its cured product may ensure impact resistance and vibration resistance, thereby ensuring product durability, depending on the application. The upper limit of the Shore OO hardness of the resin composition or its cured product may be 150, 140, 130, 120, 110, 100, 90, 95, or 80. The Shore OO hardness may be equal to or less than any one of the above upper limits. The lower limit of the Shore OO hardness may be 10, 15, 20, 25, 30, 35, 40, 45, 50, 55, 60, 65, 70, 75, 80, or 85. The Shore OO hardness may be equal to or greater than any one of the above lower limits. The Shore OO hardness may be within a range between any one of the upper limits described above and any one of the lower limits described above. The hardness of such a resin composition or its cured product may be measured by the method disclosed in the Examples below.

[0030] The resin composition or its cured product can also exhibit appropriate flexibility. For example, adjusting the flexibility of the resin composition or its cured product to a desired level can greatly expand its application range. For example, the upper limit of the bending radius of the resin composition or its cured product may be approximately 20, 19, 18, 17, 16, 15, 14, 13, 12, 11, 10, 9, or 8. The bending radius may be equal to or less than any one of the upper limits described above. The lower limit of the bending radius may be, for example, approximately 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, or 11. The bending radius may be equal to or greater than any one of the lower limits described above. The bending radius may be within a range between any one of the upper limits described above and any one of the lower limits described above. The bending radius of such a resin composition or its cured product can be measured by the method disclosed in the Examples below, and its unit is mm.

[0031] The resin composition of the present invention may be insulating. That is, the resin composition has insulating properties and / or can form a cured product having insulating properties. For example, the resin composition or its cured product may have a breakdown voltage of 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, measured in accordance with ASTM D149. A higher breakdown voltage indicates better insulating properties. While there is no particular upper limit, taking into account the composition of the resin composition, the breakdown voltage may 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. The breakdown voltage can be controlled by adjusting the insulating properties of the resin composition, for example, by incorporating an insulating filler into the resin layer. Among fillers, ceramic fillers are generally known as components that can ensure insulating properties.

[0032] The resin composition or its cured product may have flame retardancy. For example, the resin composition or its cured product may exhibit a V-0 rating in the UL94 V Test (Vertical Burning Test). This ensures stability against fires and other accidents that may be a concern depending on the application of the resin composition.

[0033] The resin composition or its cured product may have a specific gravity of 5 or less. Other examples of the specific gravity include 4.5 or less, 4 or less, 3.5 or less, or 3 or less. A resin layer having a specific gravity within this range is advantageous for providing a lighter product. The lower limit of the specific gravity is not particularly limited. For example, the specific gravity may be about 1.5 or more, or about 2 or more. The components added to the resin layer can be adjusted so that the resin composition or its cured product has the above specific gravity. For example, when adding a filler, a filler that can ensure the desired properties (e.g., thermal conductivity) even at a low specific gravity, i.e., a filler with a low specific gravity itself, or a surface-treated filler, can be used.

[0034] The resin composition may have a low shrinkage rate during or after curing. This can prevent peeling or voids that may occur during application. The shrinkage rate can be appropriately adjusted within a range that can exhibit the above-mentioned effects, and may be, for example, less than 5%, less than 3%, or less than about 1%. The lower the shrinkage rate, the more advantageous it is, so there is no particular lower limit.

[0035] The resin composition or its cured product may have a low coefficient of thermal expansion (CTE). This can prevent peeling or voids that may occur during application or use. The CTE can be appropriately adjusted within a range that can achieve the above-mentioned effects, and may be, for example, less than 300 ppm / K, less than 250 ppm / K, less than 200 ppm / K, less than 150 ppm / K, or less than about 100 ppm / K. The lower the CTE, the more advantageous it is, so there is no particular lower limit.

[0036] The resin composition or its cured product may also have a 5% weight loss temperature of 400°C or higher in thermogravimetric analysis (TGA), and an 800°C residual of 70% by weight or higher. Such characteristics can further improve high-temperature stability. In other examples, the 800°C residual may be about 75% by weight or higher, about 80% by weight or higher, about 85% by weight or higher, or about 90% by weight or higher. In other examples, the 800°C residual may be about 99% by weight or lower. The thermogravimetric analysis (TGA) is performed using a 60cm 3 The temperature can be measured in the range of 25°C to 800°C at a heating rate of 20°C / min under a nitrogen (N2) atmosphere. The thermogravimetric analysis (TGA) results can also be achieved by adjusting the composition of the resin composition. For example, the 800°C residual capacity usually depends on the type and proportion of filler contained in the resin composition, and if an excessive amount of filler is included, the residual capacity increases.

[0037] The resin composition of the present invention may include a curable component. The term "curable component" refers to a component containing one or more compounds having a functional group capable of participating in a curing reaction. In one example, the functional group capable of participating in the curing reaction may be a hydroxy group. Therefore, the curable component may include a reactive compound having a hydroxy group. In the above, the reactive compound refers to a compound having the hydroxy group and capable of participating in the curing reaction. Such a reactive compound may be a monomolecular, oligomeric, or polymeric compound.

[0038] The reactive compound having a hydroxy group may be a monofunctional compound or a polyfunctional compound, the term "monofunctional compound" meaning a reactive compound containing one hydroxy group per molecule, and the term "polyfunctional compound" meaning a reactive compound containing two or more hydroxy groups per molecule.

[0039] The reactive compound having a hydroxy group may be an oil-modifying compound described below, or may be a non-oil-modifying compound. The oil-modifying compound may be the monofunctional compound or the polyfunctional compound, and the non-oil-modifying compound may also be the monofunctional compound or the polyfunctional compound.

[0040] The polyfunctional compound is also referred to as a polyol compound in this specification. The number of hydroxy groups contained in the polyfunctional compound (polyol compound) is not particularly limited. In one example, the lower limit of the number of hydroxy groups contained in the polyfunctional compound (polyol compound) may be 2 or 3 per molecule. The number of hydroxy groups contained in the polyfunctional compound (polyol compound) may be equal to or greater than any one of the above-mentioned lower limits. The upper limit of the number of hydroxy groups contained in the polyfunctional compound (polyol compound) may be approximately 10, 9, 8, 7, 6, 5, 4, 3, or 2 per molecule. The number of hydroxy groups contained in the polyfunctional compound (polyol compound) may be equal to or less than any one of the above-mentioned upper limits. The number of hydroxy groups contained in the polyfunctional compound (polyol compound) may be within the range between any one of the above-mentioned lower limits and any one of the above-mentioned upper limits. The number of hydroxy groups contained in the polyfunctional compound (polyol compound) is 1 This can be confirmed by H NMR, 1 The number of hydroxy groups can be confirmed based on the peak present in the region of 3 to 4 ppm in H NMR.

[0041] The reactive compound may be an oil-modifying compound. The term "oil-modifying compound" refers to a compound that contains a hydroxy group and a linear or branched hydrocarbon group having 3 or more carbon atoms at its end. Therefore, a reactive compound that does not contain a linear or branched hydrocarbon group having 3 or more carbon atoms at its end is also referred to as a non-oil-modifying compound in this specification. Whether a reactive compound contains the hydrocarbon group depends on the following: 1 This can be confirmed by H NMR, 1The presence and number of these hydrocarbon groups can be confirmed based on the peak in the 4-5 ppm region of H NMR. By using the oil-modified compound, polyurethane materials can be formed, and low adhesion to specific materials can be ensured without using or minimizing the use of adhesive strength-reducing ingredients such as plasticizers.

[0042] The lower limit of the number of carbon atoms in the linear or branched hydrocarbon group contained at the end of the oil-modified compound may be about 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, or 17. The number of carbon atoms may be equal to or greater than any one of the aforementioned lower limits. The upper limit of the number of carbon atoms may be about 50, 49, 48, 47, 46, 45, 44, 43, 42, 41, 40, 39, 38, 37, 36, 35, 34, 33, 32, 31, 30, 29, 28, 27, 26, 25, 24, 23, 22, 21, 20, 19, 18, 17, 16, 15, 14, 13, 12, 11, 10, 9, or 8. The number of carbon atoms may be equal to or less than any one of the upper limits. The number of carbon atoms may be within a range between any one of the lower limits and any one of the upper limits.

[0043] The linear or branched hydrocarbon group may or may not contain a double bond. If it contains a double bond, the double bond may be a conjugated double bond or a cis double bond.

[0044] Specific examples of the hydrocarbon group include an alkyl group, an alkenyl group, and an alkynyl group. In one example, the hydrocarbon group may be linked to the polyol compound via a carbonyl group or a carbonyloxy group. In this case, the hydrocarbon group may be an alkylcarbonyl group, an alkenylcarbonyl group, an alkynylcarbonyl group, an alkylcarbonyloxy group, an alkenylcarbonyloxy group, or an alkynylcarbonyloxy group. In the above, the number of carbon atoms in the alkyl group, alkenyl group, or alkynyl group may be equal to or greater than any one of the lower limits of the number of carbon atoms in the linear or branched hydrocarbon group, equal to or less than any one of the upper limits of the number of carbon atoms in the linear or branched hydrocarbon group, or may be within a range between any one of the lower limits of the number of carbon atoms in the linear or branched hydrocarbon group and any one of the upper limits of the number of carbon atoms in the linear or branched hydrocarbon group.

[0045] The alkyl group, alkenyl group, or alkynyl group may be linear or branched, and may be optionally substituted with one substituent. If a substituent is present, the type of the substituent is not particularly limited, and examples of the substituent include halogen atoms such as fluorine.

[0046] In one example, the hydrocarbon group may be included in the substituent of the following chemical formula 1:

[0047] [ka]

[0048] In Chemical Formula 1, R is a hydrocarbon group which may be linear or branched.

[0049] In Chemical Formula 1, the symbol * means that the moiety is linked to a polyol compound. Therefore, the oxygen atom in the substituent of Chemical Formula 1 may be linked to a polyol compound.

[0050] In Chemical Formula 1, the specific types of hydrocarbon groups represented by R are as described above. Therefore, the content regarding the number, type, shape, and substituents of carbon atoms of the hydrocarbon groups described above can be applied in the same manner as above.

[0051] The number of hydrocarbon groups contained in the reactive compound is not particularly limited. For example, the lower limit of the number of hydrocarbon groups contained in the reactive compound may be 1 or 2 per molecule of the compound. The upper limit of the number of hydrocarbon groups contained in the reactive compound may be approximately 10, 9, 8, 7, 6, 5, 4, 3, or 2 per molecule of the compound. The number of hydrocarbon groups may be equal to or greater than any one of the lower limits described above, equal to or less than any one of the upper limits described above, or within a range between any one of the lower limits described above and any one of the upper limits described above.

[0052] The oil-modifying compound can have a variety of forms as long as it contains the hydroxy group and hydrocarbon group.

[0053] In one example, the oil-modified compound may be a compound in which at least a portion of the hydrogen atoms of a hydrocarbon compound such as an alkane, alkene, or alkyne are substituted with the hydroxy group and / or hydrocarbon group. The number of carbon atoms in the hydrocarbon compound such as an alkane, alkene, or alkyne may be, for example, 1 to 20, 1 to 16, 1 to 8, or 4 to 6. Such a hydrocarbon compound such as an alkane, alkene, or alkyne may be linear, branched, or cyclic. Furthermore, the hydroxy group and / or hydrocarbon group may be substituted on the same carbon atom in the alkane, alkene, or alkyne, or on a different carbon atom.

[0054] In another example, the reactive compound may be a compound having a polyester skeleton or a polyether skeleton, and in this case, the reactive compound may be an oligomeric compound or a polymeric compound.

[0055] In one example, when the reactive compound having a polyester skeleton is a polyol compound, the compound is a so-called polyester polyol, and may be a polyol having a structure in which the hydrocarbon group is linked to such a polyester polyol.

[0056] Furthermore, when the reactive compound having a polyether skeleton is a polyol compound, the compound is a so-called polyether polyol, and may be a polyol having a structure in which the hydrocarbon group is linked to such a polyether polyol.

[0057] In one example, the polyester skeleton may be a so-called polycaprolactone skeleton, and the polyether skeleton may be a so-called polyalkylene skeleton.

[0058] In one example, the polyester skeleton may be a skeleton having a repeating unit represented by the following Chemical Formula 2:

[0059] [ka]

[0060] In Chemical Formula 2, X1 and X2 are each independently a single bond or an oxygen atom, L1 may be an alkylene group or an alkylidene group, and n is an arbitrary number.

[0061] As used herein, the term "single bond" refers to a bond where no atom is present at the site.

[0062] In Chemical Formula 2, the alkylene group may be, for example, an alkylene group having 2 to 20 carbon atoms, 4 to 20 carbon atoms, 4 to 16 carbon atoms, 4 to 12 carbon atoms, or 4 to 8 carbon atoms, and may be linear or branched.

[0063] In Chemical Formula 2, the alkylidene group may be, for example, an alkylidene group having 1 to 20 carbon atoms, 4 to 20 carbon atoms, 4 to 16 carbon atoms, 4 to 12 carbon atoms, or 4 to 8 carbon atoms, and may be linear or branched.

[0064] As used herein, alkylene and alkylidene groups refer to divalent substituents formed by the removal of two hydrogen atoms from an alkane. They are distinguished from each other in that an alkylene group is a divalent substituent formed by the removal of the two hydrogen atoms from other carbon atoms of the alkane, while an alkylidene group is a divalent substituent formed by the removal of the two hydrogen atoms from one carbon atom of the alkane.

[0065] In one example, the polyester skeleton may be a polycaprolactone skeleton, and in this case, L1 in Chemical Formula 2 may be a linear alkylene group having 5 carbon atoms or a linear alkylidene group having 5 carbon atoms.

[0066] In Chemical Formula 2, n is an arbitrary number representing the number of repeating units. The lower limit of n may be, for example, about 1, 2, 3, 4, or 4.5, and the upper limit may be about 25, 20, 15, 10, or 5. The n may be equal to or greater than any one of the lower limits, equal to or less than any one of the upper limits, or within a range between any one of the lower limits and any one of the upper limits.

[0067] The skeleton of Chemical Formula 2 may be a skeleton of a so-called carboxylic acid polyol or a skeleton of a caprolactone polyol. Such skeletons can be formed by known methods. For example, the skeleton of the carboxylic acid polyol can be formed by reacting a component including a carboxylic acid and a polyol (e.g., a diol or triol), and the skeleton of the caprolactone polyol can be formed by reacting a component including caprolactone and a polyol (e.g., a diol or triol). The carboxylic acid may be a dicarboxylic acid.

[0068] In the oil-modifying compound having the skeleton of Chemical Formula 2, the hydroxy group or the hydrocarbon group described above may be present at the end of the skeleton of Chemical Formula 2.

[0069] In this case, the skeleton of Chemical Formula 2 can be represented by Chemical Formula 3 below.

[0070] [ka]

[0071] In Chemical Formula 3, X1, X2, L1, and n are as defined in Chemical Formula 2, and R1 may be a hydroxy group or a substituent of Chemical Formula 4 below.

[0072] [ka]

[0073] In Chemical Formula 4, X3 is a single bond or an oxygen atom, and R is the same as R in Chemical Formula 1.

[0074] In Chemical Formula 3, when R1 is a hydroxy group, X1 may be a single bond and X2 may be an oxygen atom; when R1 is a substituent of Chemical Formula 4, either X1 or X3 may be a single bond and the other may be an oxygen atom.

[0075] In the oil-modified compound, the lower limit of the number of skeletons of Chemical Formula 2 or 3 may be about 1 or 2, and the upper limit may be about 10, 9, 8, 7, 6, 5, 4, 3, or 2. The number of skeletons may be equal to or greater than any one of the lower limits mentioned above, equal to or less than any one of the upper limits mentioned above, or within a range between any one of the lower limits mentioned above and any one of the upper limits mentioned above.

[0076] The oil-modified compound having a polyester backbone can have a linear or branched chain structure.

[0077] In the above, the linear structure is a structure in which a main chain containing the skeleton of Chemical Formula 2 or 3 is present and no other polymer chain is linked to the main chain, and the branched chain structure may be a structure in which a chain containing the skeleton of Chemical Formula 2 or 3 is linked as a side chain to the main chain containing the skeleton of Chemical Formula 2 or 3. In the above, the number of chains containing the skeleton of Chemical Formula 2 or 3 linked as side chains in the branched chain structure may be, for example, 1 to 5, 1 to 4, 1 to 3, 1 to 2, or 1.

[0078] In one example, the oil-modified compound having a polyester skeleton may be a compound in which at least a portion of the hydrogen atoms of a hydrocarbon compound such as an alkane, alkene, or alkyne is substituted with the hydroxy group and / or the skeleton of Chemical Formula 3. The number of carbon atoms in the hydrocarbon compound such as an alkane, alkene, or alkyne may be, for example, 1 to 20, 1 to 16, 1 to 8, or 4 to 6.

[0079] The hydrocarbon compound such as an alkane, alkene, or alkyne may be linear, branched, or cyclic, and the hydroxy group and / or the skeleton of Formula 3 may be substituted on the same carbon atom in the alkane, alkene, or alkyne, or may be substituted on another carbon atom.

[0080] In one example, the polyether skeleton may be a skeleton having a repeating unit represented by the following Chemical Formula 5.

[0081] [ka]

[0082] In Chemical Formula 5, X4 and X5 are each independently a single bond or an oxygen atom, L2 may be an alkylene group or an alkylidene group, and m is an arbitrary number.

[0083] In Chemical Formula 5, the alkylene group may be, for example, an alkylene group having 2 to 20 carbon atoms, 2 to 16 carbon atoms, 2 to 12 carbon atoms, 2 to 8 carbon atoms, or 2 to 4 carbon atoms, and may be linear or branched.

[0084] In Chemical Formula 5, the alkylidene group may be, for example, an alkylidene group having 1 to 20 carbon atoms, 1 to 16 carbon atoms, 1 to 12 carbon atoms, 1 to 8 carbon atoms, or 1 to 4 carbon atoms, and may be linear or branched.

[0085] The meanings of the alkylene group and alkylidene group are as described above.

[0086] In Chemical Formula 5, m is an arbitrary number indicating the number of repeating units, and may be, for example, a number within the range of 1 to 25.

[0087] In the oil-modifying compound having the skeleton of Chemical Formula 5, the hydroxy group or the hydrocarbon group described above may be present at the end of the skeleton of Chemical Formula 5.

[0088] In this case, the skeleton of Chemical Formula 5 can be represented by Chemical Formula 6 below.

[0089] [ka]

[0090] In Chemical Formula 6, X4, X5, L2 and m are as defined in Chemical Formula 5, and R2 may be a hydroxy group or a substituent of Chemical Formula 7 below.

[0091] [ka]

[0092] In Chemical Formula 7, X6 is a single bond or an oxygen atom, and R is the same as R in Chemical Formula 1.

[0093] In Chemical Formula 6, when R2 is a hydroxy group, X4 is a single bond, and when R2 is a substituent of Chemical Formula 7, one of X4 and X6 is a single bond and the other is an oxygen atom.

[0094] The oil-modifying compound may contain one or more or two or more skeletons of Chemical Formula 5 or 6. The polyol compound may contain 10 or less, 9 or less, 8 or less, 7 or less, 6 or less, 5 or less, 4 or less, 3 or less, or 2 or less skeletons of Chemical Formula 5 or 6.

[0095] The polyol compound having a polyether skeleton may have a linear or branched chain structure.

[0096] In the above, the linear structure is a structure in which a main chain containing the skeleton of Chemical Formula 5 or 6 is present and no other polymer chain is linked to the main chain, and the branched chain structure may be a structure in which a chain containing the skeleton of Chemical Formula 5 or 6 is linked as a side chain to the main chain containing the skeleton of Chemical Formula 5 or 6. In the above, the number of chains containing the skeleton of Chemical Formula 5 or 6 linked as side chains in the branched chain structure may be, for example, 1 to 5, 1 to 4, 1 to 3, 1 to 2, or 1.

[0097] In one example, the oil-modified compound having a polyether skeleton may be a compound in which at least a portion of the hydrogen atoms of a hydrocarbon compound such as an alkane, alkene, or alkyne is substituted with a hydroxy group and / or the skeleton of Chemical Formula 5. The number of carbon atoms in the hydrocarbon compound such as an alkane, alkene, or alkyne may be, for example, 1 to 20, 1 to 16, 1 to 8, or 4 to 6.

[0098] The hydrocarbon compound such as an alkane, alkene, or alkyne may be linear, branched, or cyclic, and the hydroxy group and / or the skeleton of Formula 5 may be substituted on the same carbon atom in the alkane, alkene, or alkyne, or may be substituted on another carbon atom.

[0099] When the oil-modifying compound is an oligomeric or polymeric compound, the compound can have an appropriate level of molecular weight.

[0100] For example, the weight average molecular weight of the oligomeric or polymeric oil-modified compound may have a lower limit of about 100 g / mol, 200 g / mol, 300 g / mol, 400 g / mol, 500 g / mol, 600 g / mol, or 700 g / mol, and an upper limit of about 3,000 g / mol, 2,500 g / mol, 2,000 g / mol, 1,500 g / mol, 1,000 g / mol, or 900 g / mol. The weight average molecular weight may be equal to or greater than any one of the above lower limits, equal to or less than any one of the above upper limits, or within a range between any one of the above lower limits and any one of the above upper limits.

[0101] By using the above-mentioned oil-modified compounds, the desired physical properties can be more effectively ensured.

[0102] The oil-modified compound may be present in a suitable ratio in the resin composition. For example, the lower limit of the ratio of the oil-modified compound in the resin composition may be about 50 wt%, 55 wt%, 60 wt%, 65 wt%, 70 wt%, 75 wt%, 80 wt%, or 85 wt%, and the upper limit may be about 95 wt% or 90 wt%. The ratio may be equal to or greater than any one of the lower limits, equal to or less than any one of the upper limits, or within a range between any one of the lower limits and any one of the upper limits.

[0103] The content of the oil-modified compound is the content in the one-component composition when the resin composition is a one-component composition, and the content in the part in which the oil-modified compound is present when the resin composition is a two-component composition. For example, when a two-component composition contains a physically separated base part and a hardener part, and the oil-modified compound is contained in the base part, the content of the oil-modified compound may be the content based on the total weight of the base part. Furthermore, when the resin composition contains a solvent and / or a filler, the content is the content based on the weight excluding the contents of the solvent and filler.

[0104] In another example, when the resin composition contains a filler component described below, the weight ratio of the oil-modified compound relative to 100 parts by weight of the filler component may be about 1 part by weight, 2 parts by weight, 3 parts by weight, 4 parts by weight, 5 parts by weight, 6 parts by weight, 7 parts by weight, 8 parts by weight, 9 parts by weight, or 10 parts by weight, and the upper limit may be about 30 parts by weight, 28 parts by weight, 26 parts by weight, 24 parts by weight, 22 parts by weight, 20 parts by weight, 18 parts by weight, 16 parts by weight, 14 parts by weight, or 12 parts by weight. The ratio may be equal to or greater than any one of the lower limits described above, equal to or less than any one of the upper limits described above, or within a range between any one of the lower limits described above and any one of the upper limits described above.

[0105] The ratio relative to the filler component is the ratio relative to 100 parts by weight of the total filler components contained in the resin composition if the resin composition is a one-component type, and is the ratio relative to 100 parts by weight of the total filler components present in the part (main part or hardener part) containing the oil-modified polyol if the resin composition is a two-component type.

[0106] The oil-modified compound can be synthesized by a known synthesis method. That is, the compound can be prepared by reacting a compound capable of introducing a hydrocarbon group corresponding to the oil-modified moiety with a known polyol compound or alcohol compound. In the above, a polyol compound is a compound having two or more hydroxy groups per molecule, and an alcohol compound is a compound having one hydroxy group per molecule. Examples of compounds capable of introducing a hydrocarbon group include saturated or unsaturated fatty acids, such as butyric acid, caproic acid, 2-ethylhexanoic acid, caprylic acid, isononanoic acid, capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, linoleic acid, and oleic acid, but are not limited thereto.

[0107] Furthermore, the type of polyol or alcohol compound to be reacted with the saturated or unsaturated fatty acid is not particularly limited, and for example, an appropriate type of general reactive compound described below can be applied, but is not limited thereto.

[0108] The reactive compound having hydroxy may further include a reactive compound different from the oil-modifying compound. In such a case, the reactive compound does not include the aforementioned hydrocarbon group, i.e., a straight-chain or branched-chain hydrocarbon group having 3 or more carbon atoms. For convenience, such a reactive compound is also referred to as a non-oil-modifying compound in this specification.

[0109] The non-oil-modified compound also contains one or more hydroxy groups per molecule. The lower limit of the number of hydroxy groups contained in the non-oil-modified compound may be about 1, 2, or 3, and the upper limit may be about 10, 9, 8, 7, 6, 5, 4, 3, or 2. The number of hydroxy groups may be equal to or greater than any one of the above-mentioned lower limits, equal to or less than any one of the above-mentioned upper limits, or within a range between any one of the above-mentioned lower limits and any one of the above-mentioned upper limits.

[0110] The non-oil-modifying compounds may also be monomolecular, oligomeric or polymeric compounds.

[0111] The non-oil-modifying compounds can have a variety of forms.

[0112] In one example, the non-oil-modifying compound may be a polyester polyol. As the polyester polyol, for example, a so-called carboxylic acid polyol or a caprolactone polyol can be used.

[0113] In one example, the polyester polyol may have a skeleton having a repeating unit represented by the following chemical formula 8:

[0114] [ka]

[0115] In Chemical Formula 8, X7 and X8 are each independently a single bond or an oxygen atom, L3 may be an alkylene group or an alkylidene group, and p is an arbitrary number.

[0116] In Chemical Formula 8, the alkylidene group may be, for example, an alkylidene group having 1 to 20 carbon atoms, 4 to 20 carbon atoms, 4 to 16 carbon atoms, 4 to 12 carbon atoms, or 4 to 8 carbon atoms, and may be linear or branched.

[0117] In Chemical Formula 8, the alkylene group may be, for example, an alkylene group having 2 to 20 carbon atoms, 4 to 20 carbon atoms, 4 to 16 carbon atoms, 4 to 12 carbon atoms, or 4 to 8 carbon atoms, and may be linear or branched.

[0118] When the polyester polyol is a polycaprolactone polyol, L3 in Chemical Formula 8 may be a linear alkylene group having 5 carbon atoms.

[0119] In addition, in the above chemical formula 8, p is an arbitrary number indicating the number of repeating units, and may be a number within the range of 1 to 25, for example.

[0120] The polyester polyol having the skeleton of Formula 8 may be a so-called carboxylic acid polyol or caprolactone polyol. Such polyol compounds may be formed by known methods. For example, the carboxylic acid polyol may be formed by reacting a component containing a carboxylic acid with a polyol (e.g., a diol or triol), and the caprolactone polyol may be formed by reacting a component containing caprolactone with a polyol (e.g., a diol or triol). The carboxylic acid may be a dicarboxylic acid.

[0121] In the polyol compound having the skeleton of Chemical Formula 8, the hydroxy group may be present at the terminal of the skeleton of Chemical Formula 8 or at another site of the polyester polyol.

[0122] When the non-oil-modified compound contains the skeleton of Formula 8, the lower limit of the number of skeletons may be about 1 or 2, and the upper limit may be about 10, 9, 8, 7, 6, 5, 4, 3, 2, or 1. The number of skeletons may be equal to or greater than any one of the lower limits mentioned above, equal to or less than any one of the upper limits mentioned above, or within a range between any one of the lower limits mentioned above and any one of the upper limits mentioned above.

[0123] The polyol compound having a polyester skeleton may have a linear or branched chain structure.

[0124] The linear structure described above is a structure in which a main chain containing the skeleton of Chemical Formula 8 is present and no other polymer chains are linked to the main chain, and the branched structure may be a structure in which a chain containing the skeleton of Chemical Formula 8 is linked as a side chain to the main chain containing the skeleton of Chemical Formula 8. In the branched structure described above, the number of chains containing the skeleton of Chemical Formula 8 linked as side chains may be, for example, 1 to 5, 1 to 4, 1 to 3, 1 to 2, or 1.

[0125] Other examples of the non-oil-modified compound include polyols having polycaprolactone polyol units or alkanediol units, polyol units, and dicarboxylic acid units. Such polyols may be mixtures of the polycaprolactone polyol units, alkanediols, polyols, and dicarboxylic acids, or may be reaction products thereof. In this case, examples of the alkanediol include diol compounds having 1 to 20 carbon atoms, 4 to 20 carbon atoms, 4 to 16 carbon atoms, or 4 to 12 carbon atoms, such as 3-methyl-1,5-pentanediol, 1,9-nonanediol, and 1,6-hexanediol. Examples of the polyol unit include alkanes or polycarbonates having 1 to 20, 4 to 20, 4 to 16, or 4 to 12 carbon atoms substituted with 3 to 10, 3 to 9, 3 to 8, 3 to 7, 3 to 6, 3 to 5, or 3 to 4 hydroxy groups, such as trimethylolpropane. Examples of the dicarboxylic acid include adipic acid, terephthalic acid, isophthalic acid, and sebacic acid. Polyol compounds of this type are known to the public under the trade names of, for example, P-510, P-1010, P-2010, P-3010, P-4010, P-5010, P-6010, F-510, F-1010, F-2010, F-3010, P-2011, P-520, P-2020, P-1012, P-2012, P-630, P-2030, P-2050, or N-2010 manufactured by Kuraray.

[0126] As the non-oil-modified compound, a polyol having a weight-average molecular weight in the range of 100 g / mol to 5,000 g / mol can be used. By using such a polyol, the desired effect can be achieved more effectively.

[0127] The curable component of the curable composition of the present invention may be composed of any one of the reactive compounds described above, or may be composed of a mixture of two or more of them.

[0128] In one example, the curable component may include a monofunctional compound (also referred to as a first reactive compound) and a polyfunctional compound (also referred to as a second reactive compound) among the reactive compounds described above. In this case, the monofunctional compound and the polyfunctional compound may each independently be the oil-modified compound or a non-oil-modified compound.

[0129] In such cases, the lower limit of the weight ratio of the monofunctional compound to 100 parts by weight of the polyfunctional compound may be, for example, about 10 parts by weight, 20 parts by weight, 30 parts by weight, 40 parts by weight, 50 parts by weight, 60 parts by weight, 70 parts by weight, 80 parts by weight, or 95 parts by weight, and the upper limit may be, for example, about 200 parts by weight, 190 parts by weight, 180 parts by weight, 170 parts by weight, 160 parts by weight, 150 parts by weight, 140 parts by weight, 130 parts by weight, 120 parts by weight, 110 parts by weight, or 105 parts by weight. The ratio may be equal to or greater than any one of the lower limits, equal to or less than any one of the upper limits, or within a range between any one of the lower limits and any one of the upper limits.

[0130] In the above case, the curable component may contain, as the second reactive compound, a reactive compound having two hydroxy groups (also referred to as a third reactive compound) and a reactive compound having three or more hydroxy groups (also referred to as a fourth reactive compound). The upper limit of the number of hydroxy groups contained in the fourth reactive compound may be about 10, 9, 8, 7, 6, 5, 4, or 3 per molecule. The number of hydroxy groups in the fourth reactive compound may be 3 or more and may be equal to or less than any one of the above-mentioned upper limits.

[0131] In such a case, the lower limit of the weight ratio of the fourth reactive compound to 100 parts by weight of the third reactive compound may be, for example, about 1 part by weight, 2 parts by weight, 3 parts by weight, 4 parts by weight, 5 parts by weight, 6 parts by weight, 7 parts by weight, 8 parts by weight, 9 parts by weight, or 10 parts by weight, and the upper limit may be, for example, about 20 parts by weight, 19 parts by weight, 18 parts by weight, 17 parts by weight, 16 parts by weight, 15 parts by weight, 14 parts by weight, 13 parts by weight, or 12 parts by weight. The ratio may be equal to or greater than any one of the lower limits mentioned above, equal to or less than any one of the upper limits mentioned above, or within a range between any one of the lower limits mentioned above and any one of the upper limits mentioned above.

[0132] The first to fourth reactive compounds may each independently be the oil-modified compounds described above, or may be non-oil-modified compounds.

[0133] In a suitable example, among the first to fourth reactive compounds, the first reactive compound and the third reactive compound may be oil-modifying compounds.

[0134] In such a case, the fourth reactive compound may be an oil-modified compound or a non-oil-modified compound, and may be the non-oil-modified compound in an appropriate example. As the non-oil-modified compound, for example, the above-mentioned polycaprolactone polyol unit or alkanediol unit; a compound containing a polyol unit and a dicarboxylic acid unit can be used.

[0135] The resin composition may contain further components, for example, a curing agent that reacts with the curable component.

[0136] Various types of curing agents can be used. In the case of a polyurethane composition, which is a resin composition, a polyisocyanate (also referred to as a polyisocyanate compound) can be used as the curing agent. The term "polyisocyanate" refers to a compound having two or more isocyanate groups. The lower limit of the number of isocyanate groups in the polyisocyanate may be about 2 or 3, and the upper limit may be about 10, 9, 8, 7, 6, 5, 4, 3, or 2. The number of isocyanate groups may be equal to or greater than any one of the lower limits, equal to or less than any one of the upper limits, or within a range between any one of the lower limits and any one of the upper limits.

[0137] The type of polyisocyanate used as the curing agent is not particularly limited, but in order to ensure the desired physical properties, a non-aromatic polyisocyanate containing no aromatic group can be used.

[0138] If necessary, both difunctional polyisocyanates and trifunctional or higher functional polyisocyanates can be used as the polyisocyanate. In the above, difunctional means that the compound contains two isocyanate groups, and trifunctional means that the compound contains three or more isocyanate groups.

[0139] Examples of polyisocyanate compounds include aliphatic polyisocyanates such as hexamethylene diisocyanate, trimethylhexamethylene diisocyanate, lysine diisocyanate, norbornane diisocyanate methyl, ethylene diisocyanate, propylene diisocyanate, and tetramethylene diisocyanate; alicyclic polyisocyanates such as transcyclohexane-1,4-diisocyanate, isophorone diisocyanate, bis(isocyanatomethyl)cyclohexane diisocyanate, and dicyclohexylmethane diisocyanate; and carbodiimide-modified polyisocyanates and isocyanurate-modified polyisocyanates containing one or more of the above. Polyisocyanates may also be used as the polyisocyanate, including addition products of the above diisocyanates and polyols (e.g., trimethylolpropane). Mixtures of two or more of the compounds listed above may also be used.

[0140] The amount of polyisocyanate used can be adjusted in consideration of the number of hydroxy groups present in the curable component contained in the resin composition and the physical properties after curing.

[0141] For example, the polyisocyanate may be included in the resin composition so that the equivalent ratio (OH / NCO) of the number of hydroxy groups (OH) present in the curable component to the number of isocyanate groups (NCO) present in the polyisocyanate is within a predetermined range.

[0142] The method for calculating the equivalent ratio (OH / NCO) is well known.

[0143] For example, if the resin composition is a two-component type, the curable component is contained in the base part, and the polyisocyanate is contained in the curing agent part, the equivalent ratio OH / NCO can be calculated by the following general formula 1.

[0144]

number

[0145] In the general formula 1, E is the equivalent ratio OH / NCO, and D m is the density of the base part, and D c is the density of the cured part, A is calculated by the following general formula 2, B is calculated by the following general formula 3, and D NCO is the Dalton mass of the isocyanate group, 42 Da, and D OH is the Dalton mass of the hydroxy group, 17 Da.

[0146]

number

[0147] In general formula 2, W OH is the weight ratio of the reactive compound present in the base part, and OH % is the W OH is the proportion of hydroxy groups contained in the reactive compound having a weight proportion of

[0148]

number

[0149] In general formula 3, W NCO is the weight fraction of polyisocyanate present in the hardener part, and NCO % is the W NCO is the proportion of isocyanate groups contained in a polyisocyanate having a weight ratio of

[0150] In the above, W OH is the weight % of each reactive compound present in the main component (based on the total weight of the main component), and the OH% of the compound is the % of hydroxy groups contained in 1 mole of each reactive compound, which is calculated by dividing the product of the number of moles of hydroxy groups contained in a single reactive compound and the molar mass of the hydroxy groups by the molar mass of the single reactive compound, and then multiplying by 100.

[0151] In the above, W NCOis the weight percent of each polyisocyanate present in the hardener part (based on the total weight of the hardener part), and the NCO % is the percentage of NCO groups contained in 1 mole of each polyisocyanate, and is calculated by dividing the product of the number of moles of NCO groups contained in a single polyisocyanate and the molar mass of the NCO groups by the molar mass of the single polyisocyanate, and then multiplying the result by 100.

[0152] In general formula 1, the Dalton mass is a constant.

[0153] The lower limit of the equivalent ratio (OH / NCO) may be, for example, about 50, 60, 70, 80, 90, 100, 110, 120, 130, 140, 150, 160, 170, 180, 190, 200, 210, 220, 230, 240, 250, or 260, and the upper limit may be, for example, about 1,000, 900, 800, 700, 600, 500, 400, 300, 290, 280, 270, 260, 250, 240, 230, 220, 210, 200, 190, 180, 170, 160, 150, 140, 130, 120, 110, or 100. The equivalent ratio may be equal to or greater than any one of the lower limits mentioned above, equal to or less than any one of the upper limits mentioned above, or within a range between any one of the lower limits mentioned above and any one of the upper limits mentioned above.

[0154] The resin composition may further include a filler component. The term "filler component" means a component consisting of a filler, i.e., a component containing only a filler.

[0155] In one example, the filler component may contain two or more fillers having different average particle sizes. In another example, the filler component may contain three or more fillers having different average particle sizes, or may consist of three to six, three to five, three to four, or three fillers having different average particle sizes. That is, in one example, the filler component may contain only three to six, three to five, three to four, or three fillers having different average particle sizes.

[0156] In another example, the filler component may exhibit at least two peaks in a particle size distribution volume curve measured using laser diffraction. In one example, the filler component may exhibit three or more peaks, or three to six, three to five, three to four, or three peaks in a particle size distribution volume curve. For example, the range of filler components exhibiting three peaks does not include filler components exhibiting one, two, or four or more peaks.

[0157] The average particle size of the filler of the present invention means the particle size at which the cumulative volume reaches 50% on the volume curve of the particle size distribution measured by laser diffraction, which is also called the median diameter. That is, in the present invention, the particle size distribution is determined on a volume basis by laser diffraction, and the particle size at the point where the cumulative value reaches 50% on the cumulative curve with the total volume set to 100% is defined as the average particle size. In other examples, this average particle size is called the median diameter or D50 particle size.

[0158] Therefore, the two fillers having different average particle sizes above may mean fillers having different particle sizes at the point where the cumulative value reaches 50% on the volume curve of the particle size distribution.

[0159] Usually, when two or more fillers having different average particle diameters are mixed to form a filler component, the volume curve of the particle size distribution measured by laser diffraction of the filler component shows peaks corresponding to the types of fillers mixed. Therefore, for example, when a filler component is formed by mixing three fillers having different average particle diameters, the volume curve of the particle size distribution of the filler component measured by laser diffraction shows three peaks.

[0160] The filler component of the resin composition of the present invention may be a thermally conductive filler component. The term "thermally conductive filler component" means a filler component that functions to cause the resin composition or a cured product thereof to exhibit the above-mentioned thermal conductivity.

[0161] In one example, the filler component may include at least a first filler having an average particle size of 60 μm to 200 μm, a second filler having an average particle size in the range of 10 μm to 30 μm, and a third filler having an average particle size of 5 μm or less.

[0162] In other examples, the first filler may have an average particle size of about 62 μm or more, 64 μm or more, 66 μm or more, or about 68 μm or more, and / or about 195 μm or less, 190 μm or less, 185 μm or less, 180 μm or less, 175 μm or less, 170 μm or less, 165 μm or less, 160 μm or less, 155 μm or less, 150 μm or less, 145 μm or less, 140 μm or less, 135 μm or less, 130 μm or less, 125 μm or less, about 120 μm or less, 115 μm or less, 110 μm or less, 105 μm or less, 100 μm or less, 95 μm or less, 90 μm or less, 85 μm or less, 80 μm or less, or about 75 μm or less.

[0163] In other examples, the second filler may have an average particle size of about 12 μm or more, 13 μm or more, 14 μm or more, 15 μm or more, 16 μm or more, 17 μm or more, 18 μm or more, 19 μm or more, or 20 μm or more, and / or about 29 μm or less, 28 μm or less, 27 μm or less, 26 μm or less, 25 μm or less, 24 μm or less, 23 μm or less, 22 μm or less, 21 μm or less, or about 20 μm or less.

[0164] In other examples, the third filler may have an average particle size of about 0.01 μm or more, 0.1 μm or more, about 0.5 μm or more, 1 μm or more, 1.5 μm or more, or 2 μm or more, and / or about 5 μm or less, 4.5 μm or less, about 4 μm or less, 3.5 μm or less, 3 μm or less, 2.5 μm or less, or 2 μm or less.

[0165] In the filler component, the ratio (D1 / D3) of the average particle size (D1) of the first filler to the average particle size (D3) of the third filler can be in the range of 25-300.

[0166] In one example, when the filler component includes two or more fillers with different average particle diameters, the third filler may be the filler with the smallest average particle diameter among the fillers included in the filler component, and when the filler component includes two or more fillers with different average particle diameters among the fillers included in the filler component, the first filler may be the filler with the largest average particle diameter among the fillers included in the filler component. In this state, the particle diameter ratio can be satisfied.

[0167] In other examples, the ratio (D1 / D3) is 26 or more, 27 or more, 28 or more, 29 or more, 30 or more, 31 or more, 32 or more, 33 or more, 34 or more, 35 or more, 40 or more, 50 or more, 60 or more, 70 or more, 80 or more, 90 or more, 100 or more, 110 or more, 120 or more, 130 or more, 140 or more, 150 or more, 160 or more, 170 or more, 180 or more, 190 or more, 200 or more, 210 or more It can also be further adjusted within the ranges of 220 or more, 230 or more, or 235 or more and / or 290 or less, 280 or less, 270 or less, 260 or less, 250 or less, 240 or less, 220 or less, 200 or less, 180 or less, 160 or less, 140 or less, 120 or less, about 100 or less, 95 or less, 90 or less, 85 or less, 80 or less, about 75 or less, 70 or less, 65 or less, or about 60 or less.

[0168] In the filler component, the ratio (D1 / D2) of the average particle size (D1) of the first filler to the average particle size (D2) of the second filler may be within a range of about 3 to 20. In other examples, the ratio (D1 / D2) may be 3.1 or more, 3.2 or more, 3.3 or more, 3.4 or more, or 3.5 or more, or may be about 19 or less, 18 or less, 17 or less, 16 or less, 15 or less, 14 or less, 13 or less, 12 or less, 11 or less, 10 or less, 9 or less, 8 or less, 7 or less, 6 or less, 5 or less, or 4 or less.

[0169] Examples of fillers that can be used include ceramic fillers 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), aluminum hydroxide (Al(OH)3), magnesium hydroxide (Mg(OH)2), calcium carbonate (CaCO3), and / or boehmite. These fillers are advantageous for meeting the thermal conductivity requirements described above, and the use of ceramic fillers can also meet the aforementioned insulation requirements.

[0170] The upper limit of the proportion of the filler component in the resin composition may be about 95% by weight, 94.5% by weight, 94% by weight, 93.5% by weight, 93% by weight, 92.5% by weight, 92% by weight, 91.5% by weight, 91% by weight, 90.5% by weight, 90.0% by weight, 89.5% by weight, or 89.0% by weight, and the lower limit may be about 70% by weight, 71% by weight, 72% by weight, 73% by weight, 74% by weight, about 75% by weight, 76% by weight, 77% by weight, 78% by weight, 79% by weight, 80% by weight, 81% by weight, 82% by weight, 83% by weight, 84% by weight, 85% by weight, 86% by weight, 87% by weight, or 88% by weight. The ratio may be greater than or equal to any one of the aforementioned lower limits, less than or equal to any one of the aforementioned upper limits, or within a range between any one of the aforementioned lower limits and any one of the aforementioned upper limits.

[0171] The ratio of the filler component relative to 100 parts by weight of the total weight of the curable component or the reactive compounds present in the curable component may be about 500 parts by weight, 550 parts by weight, 600 parts by weight, 650 parts by weight, 700 parts by weight, 750 parts by weight, 800 parts by weight, or 850 parts by weight, and the upper limit may be about 2,000 parts by weight, 1,800 parts by weight, 1,600 parts by weight, 1,400 parts by weight, 1,200 parts by weight, 1,000 parts by weight, 950 parts by weight, or 900 parts by weight. The ratio may be equal to or greater than any one of the above lower limits, equal to or less than any one of the above upper limits, or within a range between any one of the above lower limits and any one of the above upper limits.

[0172] The content of the filler component is a proportion based on the total weight of the resin composition when the resin composition is a one-component composition, and may be a proportion based on the total weight of the base component and hardener component of the two-component composition when the resin composition is a two-component resin composition, or may be a proportion based on the total weight of the base component or hardener component alone.

[0173] When the resin composition is a two-component composition, it is appropriate to divide the filler component to be applied to the final cured product in substantially equal amounts and introduce it into each of the base and curing agent parts.

[0174] The filler component may contain various types of fillers, in addition to the thermally conductive filler, if necessary. For example, carbon fillers such as graphite, fumed silica, or clay may be used.

[0175] The resin composition may further contain necessary components in addition to the components described above.

[0176] In one example, the resin composition may further include a plasticizer. As described above, in the present invention, low adhesive strength to a specific material can be ensured without using a plasticizer, but a small amount of plasticizer can be used if necessary.

[0177] The type of plasticizer that can be used is not particularly limited, and examples thereof include phthalate-based plasticizers such as dioctyl phthalate (DOP), dibutyl phthalate (DBP), butylbenzyl phthalate (BBP), diisononyl phthalate (DINP), and polyethyleneterephthalate (PET); adipate-based plasticizers such as dioctyl adipate (DOA) and diisononyl adipate (DINA); fatty acid-based plasticizers; phosphate-based plasticizers; and polyester-based plasticizers.

[0178] When a plasticizer is included, its proportion can be adjusted depending on the purpose. For example, the lower limit of the proportion of the plasticizer relative to 100 parts by weight of the total weight of the curable component or the reactive compounds present in the curable component may be about 0.5 parts by weight, 1 part by weight, 1.5 parts by weight, 2 parts by weight, 2.5 parts by weight, 3 parts by weight, 3.5 parts by weight, 4 parts by weight, 4.5 parts by weight, 5 parts by weight, 5.5 parts by weight, 6 parts by weight, or 6.5 parts by weight, and the upper limit may be about 20 parts by weight, 19 parts by weight, 18 parts by weight, 17 parts by weight, 16 parts by weight, 15 parts by weight, 14 parts by weight, 13 parts by weight, 12 parts by weight, 11 parts by weight, 10 parts by weight, 9 parts by weight, 8 parts by weight, or 7 parts by weight. The proportion may be equal to or greater than any one of the above lower limits, equal to or less than any one of the above upper limits, or within a range between any one of the above lower limits and any one of the above upper limits. The ratio may be changed depending on the overall composition of the resin composition and the intended use.

[0179] The resin composition may further contain a catalyst. The type of catalyst that can be contained is not particularly limited as long as it can induce appropriate curing depending on the type of the curable component. For example, when the resin composition is a polyurethane composition and the curable component is a component that forms polyurethane, a urethane reaction catalyst can be used as the catalyst.

[0180] The urethane reaction catalyst may be any known component without any particular limitation, and examples thereof include organic catalysts such as tertiary amines and organometallic catalysts. From the viewpoint of achieving an appropriate effect through combination with a curing rate retarder described below, the catalyst may be an organometallic catalyst, and for example, a tin catalyst such as an organotin catalyst may be used.

[0181] When a catalyst is included, its proportion can be adjusted depending on the purpose. For example, the lower limit of the proportion of the catalyst relative to 100 parts by weight of the total weight of the curable component or the reactive compounds present in the curable component may be about 0.001 parts by weight, 0.005 parts by weight, 0.01 parts by weight, 0.05 parts by weight, 0.1 parts by weight, 0.5 parts by weight, or 0.55 parts by weight, and the upper limit may be about 10 parts by weight, 9 parts by weight, 8 parts by weight, 7 parts by weight, 6 parts by weight, 5 parts by weight, 4 parts by weight, 3 parts by weight, 2 parts by weight, 1 part by weight, or 0.05 parts by weight. The proportion may be equal to or greater than any one of the lower limits, equal to or less than any one of the upper limits, or within a range between any one of the lower limits and any one of the upper limits. The proportion may also be changed taking into account the overall composition of the resin composition and the intended use.

[0182] The resin composition may contain a curing rate regulator to ensure an appropriate curing rate. In the present invention, the term "curing rate regulator" refers to a component that can slow the curing rate of the resin composition compared to when the component is not present. Typically, curing of a resin composition begins when the components participating in the curing reaction are mixed under conditions that allow curing. For example, if the resin composition is a room-temperature curing type and is a two-component type containing a base component and a curing agent component, the resin composition begins to cure when the base component and the curing agent component are mixed at room temperature.

[0183] However, depending on the application of the resin composition, problems may arise if the curing rate is too fast after the start of curing as described above.

[0184] Therefore, in the present invention, the curing rate regulator can be used to ensure an appropriate curing rate, if necessary. The type of curing rate regulator to be used is not particularly limited. For example, a component that can competitively react with or exhibit affinity to the curable component and catalyst contained in the resin composition and thereby exhibit a curing rate regulation effect can be used.

[0185] When the resin composition is a polyurethane composition, the curing rate regulator may be a thiol compound or a carboxylic acid compound, and either one of the thiol compound and the carboxylic acid compound or both may be used.

[0186] As the thiol compound, for example, a compound represented by the following Chemical Formula 9 can be used.

[0187] [ka]

[0188] In Chemical Formula 9, R1 may be an alkyl group, an alkoxy group, an aromatic monovalent hydrocarbon group, or —Si(R3)3, R2 may be a single bond, an alkylene group, or an alkylidene group, and R3 may be a hydrogen atom, an alkyl group, or an alkoxy group.

[0189] In Chemical Formula 9, when R2 is a single bond, it means that R2 does not exist and the thiol (SH) group is directly linked to R1.

[0190] The alkyl group of R1 or R3 in Chemical Formula 9 may be an alkyl group having 1 to 20 carbon atoms, 1 to 16 carbon atoms, 1 to 12 carbon atoms, 1 to 8 carbon atoms, or 1 to 4 carbon atoms. Such alkyl groups may be linear, branched, or cyclic. The alkyl groups may be optionally substituted with one or more substituents, or may be unsubstituted. When substituted, examples of the substituents include, but are not limited to, halogen atoms, alkoxy groups having 1 to 4 carbon atoms, and thiol groups.

[0191] The alkoxy group of R1 or R3 in Chemical Formula 9 may be an alkoxy group having 1 to 20 carbon atoms, 1 to 16 carbon atoms, 1 to 12 carbon atoms, 1 to 8 carbon atoms, or 1 to 4 carbon atoms. Such an alkoxy group may be linear, branched, or cyclic. The alkoxy group may be optionally substituted with one or more substituents, or may be unsubstituted. When substituted, examples of the substituent include, but are not limited to, a halogen atom, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, or a thiol group.

[0192] In the above, examples of the aromatic monovalent hydrocarbon group include an aryl group or a heteroaryl group. In this case, examples of the aryl group include a phenyl group, a biphenyl group, a naphthyl group, an anthracenyl group, a phenanthryl group, a pyrenyl group, a perylenyl group, a chrysenyl group, and a fluorenyl group, and examples of the heteroaryl group include a thiophene group, a furan group, a pyrrole group, an imidazole group, a thiazole group, an oxazole group, an oxadiazole group, a triazole group, a pyridyl group, a bipyridyl group, a pyrimidyl group, a triazine group, an acridyl group, a pyridazine group, a pyrazinyl group, a quinolinyl group, a quinazoline group, a quinoxalinyl group, a phthalazinyl group, a pyridopyrimidinyl group, a pyridopyrazinyl group, a pyrazinopyrazinyl group, an isoquinoline group, an indole group, a carbazole group, a benzoxazole group, a benzimidazole group, a benzothiazole group, a benzocarbazole group, and a benzothiophene group. Examples of the aromatic monovalent hydrocarbon group include, but are not limited to, a dibenzothiophene group, a benzofuranyl group, a phenanthroline group, a thiazolyl group, an isoxazolyl group, an oxadiazolyl group, a thiadiazolyl group, and a dibenzofuranyl group. Such aromatic monovalent hydrocarbon groups may be optionally substituted with one or more substituents, or may be unsubstituted. When substituted, examples of the substituent include, but are not limited to, a halogen atom, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, and a thiol group.

[0193] In Chemical Formula 9, the alkylene group of R2 may be, for example, an alkylene group having 2 to 20 carbon atoms, 4 to 20 carbon atoms, 4 to 16 carbon atoms, 4 to 12 carbon atoms, or 4 to 8 carbon atoms, and may be linear or branched. Such an alkylene group may be optionally substituted with one or more substituents, or may be unsubstituted. If substituted, examples of the substituent include, but are not limited to, a halogen atom, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, or a thiol group. In addition, in some cases, at least one of the carbon atoms constituting the alkylene group may be substituted with an oxygen atom.

[0194] In one example, the alkylidene group of R2 in Chemical Formula 9 may be an alkylidene group having 1 to 20 carbon atoms, 4 to 20 carbon atoms, 4 to 16 carbon atoms, 4 to 12 carbon atoms, or 4 to 8 carbon atoms, and may be linear or branched. Such an alkylidene group may be optionally substituted with one or more substituents, or may be unsubstituted. If substituted, examples of the substituent include, but are not limited to, a halogen atom, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, or a thiol group. In addition, in some cases, at least one of the carbon atoms constituting the alkylidene group may be substituted with an oxygen atom.

[0195] As the thiol compound, for example, a monofunctional compound having a hydrocarbon group can be used. The hydrocarbon group may be a substituted or unsubstituted hydrocarbon group. When the hydrocarbon group is a substituted hydrocarbon group, the type of the substituent is not particularly limited, and may be, for example, a halogen, an alkoxy group having 1 to 4 carbon atoms, and / or a silyl group (e.g., a substituent represented by -Si(R3)3 in the above chemical formula 9). When the thiol compound is a monofunctional compound, it means that the compound contains one thiol group (-SH).

[0196] The hydrocarbon group of the thiol compound may be an alkyl group, an alkenyl group, or an alkynyl group. In this case, the alkyl group may be an alkyl group having 1 to 30 carbon atoms, 4 to 30 carbon atoms, 8 to 30 carbon atoms, 8 to 26 carbon atoms, 8 to 22 carbon atoms, 8 to 18 carbon atoms, or 8 to 14 carbon atoms, and this alkyl group may be linear or branched. The alkenyl group or alkynyl group may be an alkenyl group or alkynyl group having 2 to 30 carbon atoms, 4 to 30 carbon atoms, 8 to 30 carbon atoms, 8 to 26 carbon atoms, 8 to 22 carbon atoms, 8 to 18 carbon atoms, or 8 to 14 carbon atoms, and this alkenyl group or alkynyl group may be linear or branched.

[0197] The thiol compound may be a compound in which one hydrogen atom of a hydrocarbon compound such as an alkane, alkene, or alkyne is substituted with a thiol group (—SH). In such cases, the alkane may be an alkane having 1 to 30 carbon atoms, 4 to 30 carbon atoms, 8 to 30 carbon atoms, 8 to 26 carbon atoms, 8 to 22 carbon atoms, 8 to 18 carbon atoms, or 8 to 14 carbon atoms, and this alkane may be linear or branched. The alkene or alkyne may be an alkene or alkyne having 2 to 30 carbon atoms, 4 to 30 carbon atoms, 8 to 30 carbon atoms, 8 to 26 carbon atoms, 8 to 22 carbon atoms, 8 to 18 carbon atoms, or 8 to 14 carbon atoms, and this alkene or alkyne may be linear or branched.

[0198] The alkane, alkene, or alkyne may be optionally substituted with other substituents in addition to the thiol group, if necessary. In such cases, examples of the substituent include an alkoxy group having 1 to 4 carbon atoms and / or a silyl group (e.g., a substituent represented by -Si(R3)3 in Chemical Formula 9), but are not limited thereto.

[0199] The lower limit of the molecular weight (molar mass) of the thiol compound may be about 50 g / mol, 100 g / mol, 150 g / mol, or 200 g / mol, and the upper limit may be about 400 g / mol, 350 g / mol, 300 g / mol, or 250 g / mol. The molecular weight may be equal to or greater than any one of the lower limits, equal to or less than any one of the upper limits, or within a range between any one of the lower limits and any one of the upper limits.

[0200] There are no particular limitations on the specific type of the thiol compound, and it may be, for example, 1-dodecane thiol or (3-mercaptopropyl)triethoxysilane.

[0201] When a thiol compound is contained, its proportion can be adjusted according to the purpose. For example, the lower limit of the proportion of the thiol compound relative to 100 parts by weight of the total weight of the curable component or the reactive compounds present in the curable component may be about 0.001 parts by weight, 0.005 parts by weight, 0.01 parts by weight, 0.05 parts by weight, 0.1 parts by weight, 0.5 parts by weight, 1 part by weight, or 1.5 parts by weight, and the upper limit may be about 10 parts by weight, 9 parts by weight, 8 parts by weight, 7 parts by weight, 6 parts by weight, 5 parts by weight, 4 parts by weight, 3 parts by weight, 2 parts by weight, 1 part by weight, 0.9 parts by weight, 0.8 parts by weight, 0.7 parts by weight, 0.6 parts by weight, 0.5 parts by weight, 0.4 parts by weight, 0.3 parts by weight, or 0.2 parts by weight. The ratio may be greater than or equal to any one of the aforementioned lower limits, less than or equal to any one of the aforementioned upper limits, or within a range between any one of the aforementioned lower limits and any one of the aforementioned upper limits.

[0202] The ratio may be changed depending on the overall composition of the resin composition and the intended use.

[0203] When the thiol compound and the catalyst are both contained in the polyurethane composition, the ratio between them can be controlled.

[0204] For example, the lower limit of the weight ratio (T / U) of the thiol compound (T) to the urethane reaction catalyst (U) may be 0.1, 0.5, 1, 1.5, 2, 2.5, or 3, and the upper limit may be about 6, 5.5, 5, 4.5, 4, or 3.5. The ratio (T / U) may be equal to or greater than any one of the lower limits mentioned above, equal to or less than any one of the upper limits mentioned above, or within a range between any one of the lower limits mentioned above and any one of the upper limits mentioned above.

[0205] In the above, the carboxylic acid compound may be, for example, a monofunctional compound having a hydrocarbon group. When the carboxylic acid compound is a monofunctional compound, it means that the compound contains one carboxyl group (—COOH).

[0206] In one example, the carboxylic acid compound may be, for example, a carboxylic acid compound in which the hydrocarbon group is a saturated hydrocarbon group. Such a carboxylic acid compound may be, for example, a non-aromatic carboxylic acid compound. Such a carboxylic acid compound may be, for example, a compound in which the carbonyl group of the carboxylic acid compound is not conjugated with a π-electron system.

[0207] The hydrocarbon group of the carboxylic acid compound may be an alkyl group, an alkenyl group, or an alkynyl group. In this case, the alkyl group may be an alkyl group having 1 to 30 carbon atoms, 1 to 26 carbon atoms, 1 to 22 carbon atoms, 1 to 18 carbon atoms, 1 to 14 carbon atoms, 1 to 10 carbon atoms, 1 to 6 carbon atoms, 1 to 4 carbon atoms, 4 to 30 carbon atoms, 5 to 30 carbon atoms, 5 to 26 carbon atoms, 5 to 22 carbon atoms, 5 to 18 carbon atoms, 5 to 14 carbon atoms, or 5 to 10 carbon atoms, and this alkyl group may be linear or branched. The alkenyl group or alkynyl group may be an alkenyl group or alkynyl group having 2 to 30 carbon atoms, 4 to 30 carbon atoms, 5 to 30 carbon atoms, 5 to 26 carbon atoms, 5 to 22 carbon atoms, 5 to 18 carbon atoms, 5 to 14 carbon atoms, or 5 to 10 carbon atoms, and this alkenyl group or alkynyl group may be linear or branched.

[0208] The carboxylic acid compound may be a compound in which one hydrogen atom of a hydrocarbon compound such as an alkane, alkene, or alkyne is substituted with a carboxyl group (—COOH). In this case, the alkane may be an alkane having 1 to 30 carbon atoms, 1 to 26 carbon atoms, 1 to 22 carbon atoms, 1 to 18 carbon atoms, 1 to 14 carbon atoms, 1 to 10 carbon atoms, 1 to 6 carbon atoms, 1 to 4 carbon atoms, 4 to 30 carbon atoms, 5 to 30 carbon atoms, 5 to 26 carbon atoms, 5 to 22 carbon atoms, 5 to 18 carbon atoms, 5 to 14 carbon atoms, or 5 to 10 carbon atoms, and this alkane may be linear or branched. The alkene or alkyne may be an alkene or alkyne having 2 to 30 carbon atoms, 4 to 30 carbon atoms, 5 to 30 carbon atoms, 5 to 26 carbon atoms, 5 to 22 carbon atoms, 5 to 18 carbon atoms, 5 to 14 carbon atoms, or 5 to 10 carbon atoms, and the alkene or alkyne may be linear or branched.

[0209] The lower limit of the molecular weight (molar mass) of the carboxylic acid compound may be about 50 g / mol, 70 g / mol, 90 g / mol, 110 g / mol, 130 g / mol, or 140 g / mol, and the upper limit may be about 400 g / mol, 350 g / mol, 300 g / mol, 250 g / mol, 200 g / mol, 150 g / mol, or 100 g / mol. The molecular weight may be equal to or greater than any one of the lower limits mentioned above, equal to or less than any one of the upper limits mentioned above, or within a range between any one of the lower limits mentioned above and any one of the upper limits mentioned above.

[0210] The carboxylic acid compound may have a pKa within a predetermined range. The lower limit of the pKa of the compound may be about 2, 2.5, 3, 3.5, 4, or 4.5, and the upper limit may be about 9, 8.5, 8, 7.5, 7, 6.5, 6, 5.5, or 5. The pKa may be equal to or greater than any one of the lower limits, equal to or less than any one of the upper limits, or within a range between any one of the lower limits and any one of the upper limits. The ratio may be changed depending on the overall composition of the resin composition and the intended use.

[0211] The specific type of the carboxylic acid compound is not particularly limited, and may be, for example, acetic acid, stearic acid, 2-ethylhexanoic acid, isononanoic acid, or oleic acid.

[0212] When a carboxylic acid compound is included, its proportion can be adjusted depending on the purpose. For example, the lower limit of the proportion of the carboxylic acid compound relative to 100 parts by weight of the total weight of the curable component or the reactive compounds present in the curable component may be about 0.001 parts by weight, 0.005 parts by weight, 0.01 parts by weight, 0.05 parts by weight, 0.1 parts by weight, 0.5 parts by weight, or 1 part by weight, and the upper limit may be about 10 parts by weight, 9 parts by weight, 8 parts by weight, 7 parts by weight, 6 parts by weight, 5 parts by weight, 4 parts by weight, 3 parts by weight, 2 parts by weight, 1 part by weight, 0.9 parts by weight, 0.8 parts by weight, 0.7 parts by weight, 0.6 parts by weight, 0.5 parts by weight, 0.4 parts by weight, 0.3 parts by weight, or 0.2 parts by weight. The proportion may be equal to or greater than any one of the lower limits, equal to or less than any one of the upper limits, or within a range between any one of the lower limits and any one of the upper limits. The ratio may be changed depending on the overall composition of the resin composition and the intended use.

[0213] When the carboxylic acid compound and the catalyst are both contained in the polyurethane composition, the ratio between them can be controlled.

[0214] For example, the lower limit of the weight ratio (C / U) of the carboxylic acid compound (C) to the urethane reaction catalyst (U) may be 0.1, 0.5, 1, 1.5, or 2, and the upper limit may be about 6, 5.5, 5, 4.5, 4, 3.5, 3, 3.5, 2, 2.5, or 1. The ratio (C / U) may be equal to or greater than any one of the lower limits mentioned above, equal to or less than any one of the upper limits mentioned above, or within a range between any one of the lower limits mentioned above and any one of the upper limits mentioned above.

[0215] As described above, the curing rate regulator may be one or both of the thiol compound and the carboxylic acid compound. The carboxylic acid compound and the thiol compound may be used simultaneously to ensure a desired viscosity maintenance period after the start of curing, ensure an appropriate curing rate and curing ability after the viscosity maintenance period has elapsed, and simultaneously adjust the rate of hardness increase.

[0216] When a thiol compound and a carboxylic acid compound are both included as described above, the weight ratio (T / C) of the thiol compound (T) to the carboxylic acid compound (C) can be adjusted. The lower limit of the ratio (T / C) may be about 0.01, 0.05, 0.1, 0.5, 1, 1.5, 2, 2.5, or 3, and the upper limit may be about 10, 9.5, 9, 8.5, 8, 7.5, 7, 6.5, 6, 5.5, 5, 4.5, 4, 3.5, 3, 2.5, 2, or 1.5. The ratio (T / C) may be equal to or greater than any one of the lower limits, equal to or less than any one of the upper limits, or within a range between any one of the lower limits and any one of the upper limits.

[0217] The resin composition contains the above components and may further contain other components, if necessary. Examples of the other components that may be applied in this case include, but are not limited to, viscosity adjusters (e.g., thixotropic agents, diluents, etc.) for adjusting viscosity, for example, for increasing or decreasing viscosity or for adjusting viscosity due to shear force, dispersants, surface treatment agents, flame retardants, flame retardant aids, and / or coupling agents.

[0218] As described above, the resin composition may be a one-component composition or a two-component composition.

[0219] In the case of a two-component composition, the aforementioned components of the resin composition may be contained separately in a physically separate base part and curing agent part.

[0220] In one embodiment, the present invention relates to a composition (two-component composition) in which the resin composition is a two-component composition.

[0221] Such a two-component composition may include at least a base part and a curing agent part, and the base part and the curing agent part may be physically separate from each other. When the physically separate base part and the curing agent part are mixed, a curing reaction can be initiated. When the resin composition is a polyurethane composition, the curing reaction can result in the formation of polyurethane.

[0222] When forming a two-component composition, the base part may contain at least the curable component, catalyst, and cure rate regulator among the above-mentioned components. Also, the curing agent part may contain at least the curing agent (polyisocyanate). In the above case, the base part may not contain the curing agent (polyisocyanate), and the curing agent part may not contain the curable component, catalyst, and cure regulator.

[0223] The filler component may be contained in either one of the base and hardener parts, or in both the base and hardener parts. When the filler component is contained in both the base and hardener parts, the base and hardener parts may contain the same amount of filler component.

[0224] For example, in the above case, the upper limit of the proportion of the filler component in the base part may be about 95% by weight, 94.5% by weight, 94% by weight, 93.5% by weight, 93% by weight, 92.5% by weight, 92% by weight, 91.5% by weight, 91% by weight, 90.5% by weight, 90.0% by weight, 89.5% by weight, or 89.0% by weight, and the lower limit may be about 70% by weight, 71% by weight, 72% by weight, 73% by weight, 74% by weight, about 75% by weight, 76% by weight, 77% by weight, 78% by weight, 79% by weight, 80% by weight, 81% by weight, 82% by weight, 83% by weight, 84% by weight, 85% by weight, 86% by weight, 87% by weight, or 88% by weight. The ratio may be greater than or equal to any one of the aforementioned lower limits, less than or equal to any one of the aforementioned upper limits, or within a range between any one of the aforementioned lower limits and any one of the aforementioned upper limits.

[0225] The proportion of the filler component in the base part can also be defined as the proportion relative to 100 parts by weight of the total weight of the curable component of the base part or the reactive compound present in the curable component. For example, the lower limit of the filler component proportion may be approximately 500 parts by weight, 550 parts by weight, 600 parts by weight, 650 parts by weight, 700 parts by weight, 750 parts by weight, 800 parts by weight, or 850 parts by weight, and the upper limit may be approximately 2,000 parts by weight, 1,800 parts by weight, 1,600 parts by weight, 1,400 parts by weight, 1,200 parts by weight, 1,000 parts by weight, 950 parts by weight, or 900 parts by weight. The proportion may be equal to or greater than any one of the lower limits, equal to or less than any one of the upper limits, or within a range between any one of the lower limits and any one of the upper limits.

[0226] In the above case, the upper limit of the proportion of the filler component in the hardener part may be about 95% by weight, 94.5% by weight, 94% by weight, 93.5% by weight, 93% by weight, 92.5% by weight, 92% by weight, 91.5% by weight, 91% by weight, 90.5% by weight, 90.0% by weight, 89.5% by weight, or 89.0% by weight, and the lower limit may be about 70% by weight, 71% by weight, 72% by weight, 73% by weight, 74% by weight, about 75% by weight, 76% by weight, 77% by weight, 78% by weight, 79% by weight, 80% by weight, 81% by weight, 82% by weight, 83% by weight, 84% by weight, 85% by weight, 86% by weight, 87% by weight, or 88% by weight. The ratio may be greater than or equal to any one of the aforementioned lower limits, less than or equal to any one of the aforementioned upper limits, or within a range between any one of the aforementioned lower limits and any one of the aforementioned upper limits.

[0227] The ratio of the filler component in the curing agent part can also be defined as the ratio relative to 100 parts by weight of the curing agent (polyisocyanate) in the curing agent part. For example, the lower limit of the filler component ratio may be approximately 500 parts by weight, 550 parts by weight, 600 parts by weight, 650 parts by weight, 700 parts by weight, 750 parts by weight, 800 parts by weight, or 850 parts by weight, and the upper limit may be approximately 2,000 parts by weight, 1,800 parts by weight, 1,600 parts by weight, 1,400 parts by weight, 1,200 parts by weight, 1,000 parts by weight, 950 parts by weight, or 900 parts by weight. The ratio may be equal to or greater than any one of the lower limits, equal to or less than any one of the upper limits, or within a range between any one of the lower limits and any one of the upper limits.

[0228] Other components such as catalysts, plasticizers, and flame retardants may be contained in the base and / or hardener parts as needed.

[0229] In the two-component composition, the lower limit of the volume ratio (P / N) of the base part volume (P) to the hardener part volume (N) may be 0.8, 0.85, 0.9, 0.95, or 1, and the upper limit may be 1.2, 1.15, 1.1, 1.05, or 1. The ratio (P / N) may be equal to or greater than any one of the lower limits mentioned above, equal to or less than any one of the upper limits mentioned above, or within a range between any one of the lower limits mentioned above and any one of the upper limits mentioned above.

[0230] In one example, the two-component composition can be formulated so as to ensure the aforementioned equivalent ratio (OH / NCO) when the base part and the hardener part have the above volume ratio.

[0231] Such two-component compositions or their cured products may also exhibit the aforementioned adhesive strength to aluminum and polyester, thermal conductivity, hardness, bending radius, insulating properties, flame retardancy, specific gravity, shrinkage rate, thermal expansion coefficient, and / or 5% weight loss temperature in thermogravimetric analysis (TGA).

[0232] The resin composition (one-component or two-component composition) can exhibit an appropriate curing rate after curing initiation. In the above, curing initiation occurs when the curable component and curing agent contained in the resin composition come into contact under conditions that allow curing to begin. Therefore, in the case of a one-component composition, curing begins when the composition is placed under curing initiation conditions, and in the case of a two-component composition, curing can begin when the base component and curing agent components are mixed under curing initiation conditions.

[0233] For example, when the resin composition is a curable composition, the curable composition can exhibit a curing rate such that V1 according to the following formula 1 falls within a predetermined range.

[0234] [Formula 1] V1=V initial / t

[0235] In equation 1, Vinitial is the initial viscosity (unit: cps) of the curable composition at the start of curing, and t is the time (unit: minutes) required for the viscosity of the curable composition to double from the start of curing relative to the initial viscosity.

[0236] As previously mentioned, curing occurs when the components participating in the curing reaction come into contact under conditions that allow curing.

[0237] For example, when the curable composition is a base part including the curing component, a curing rate modifier, a urethane reaction catalyst, and a filler component, the curing initiation point may be the point at which the base part (curable composition) and the curing component (e.g., the curing component or curing part including the polyisocyanate) are mixed under conditions that allow curing. The mixing to confirm the following formula 1 may be performed so that the base part and the curing component satisfy the above-mentioned volume ratio (P / N) and / or equivalent ratio (OH / NCO).

[0238] Therefore, in such a case, the initial viscosity may be the initial viscosity of the mixture of the base part and the hardener component.

[0239] The method for determining V1 in the above formula 1 is summarized in the examples.

[0240] The lower limit of V1 in the formula 1 may be about 2,000 cps / min, 2,500 cps / min, 3,000 cps / min, 3,500 cps / min, 4,000 cps / min, 4,500 cps / min, 5,000 cps / min, 5,500 cps / min, 6,000 cps / min, or 6,500 cps / min, and the upper limit may be about 20,000 cps / min, 18,000 cps / min, 16,000 cps / min, 14,000 cps / min, 12,000 cps / min, or 16,000 cps / min. V1 may be about 10,000 cps / min, 9,500 cps / min, 9,000 cps / min, 8,500 cps / min, 8,000 cps / min, 7,500 cps / min, 7,000 cps / min, 6,500 cps / min, 6,000 cps / min, 5,500 cps / min, 5,000 cps / min, 4,500 cps / min, 4,000 cps / min, 3,500 cps / min, 3,000 cps / min, or 2,500 cps / min. V1 may be equal to or greater than any one of the lower limits described above, equal to or less than any one of the upper limits described above, or within a range between any one of the lower limits described above and any one of the upper limits described above.

[0241] In the formula 1, V initial The upper limit of V may be about 400,000 cps, 350,000 cps, 300,000 cps, 250,000 cps, 200,000 cps, or 150,000 cps, and the lower limit may be about 10,000 cps, 50,000 cps, 100,000 cps, 150,000 cps, or 200,000 cps. initial may be greater than or equal to any one of the aforementioned lower limits, less than or equal to any one of the aforementioned upper limits, or in a range between any one of the aforementioned lower limits and any one of the aforementioned upper limits.

[0242] The curable composition may exhibit a predetermined Shore OO hardness detection time after the curing initiation point. Here, the Shore OO hardness detection time refers to the time it takes for the Shore OO hardness to be first detected in the process of periodically measuring the hardness of the curable composition after the curing initiation point. That is, when the curable composition is placed under curing initiation conditions, the hardness increases as the curing progresses, and therefore, a shorter Shore OO hardness detection time indicates a faster curing rate.

[0243] In the above, the meanings of the time point at which curing starts and the curable composition for which the hardness is measured are as described in Equation 1 above.

[0244] Therefore, for example, when the curable composition is a base part including the curable component, a curing rate modifier, a urethane reaction catalyst, and a filler component, the curing initiation point may be the point at which the base part (curable composition) and the curing agent component (e.g., the curing agent component or curing agent part including the polyisocyanate) are mixed under conditions that allow curing, and the mixing may be performed so that the base part and the curing agent component satisfy the above-mentioned volume ratio (P / N) and / or equivalent ratio (OH / NCO).

[0245] In such cases, the hardness can be measured for a mixture of the base part and the hardener component.

[0246] The lower limit of the Shore OO hardness detection time may be about 60 minutes, 80 minutes, 100 minutes, 150 minutes, 200 minutes, 250 minutes, 300 minutes, 350 minutes, 400 minutes, 450 minutes, 500 minutes, 550 minutes, 600 minutes, 650 minutes, 700 minutes, or 750 minutes, and the upper limit may be about 30 hours, 28 hours, 26 hours, 24 hours, 22 hours, 20 hours, 18 hours, 16 hours, 14 hours, 12 hours, 10 hours, 9 hours, 8 hours, 7 hours, 6 hours, 5 hours, or 4 hours. The detection time may be equal to or greater than any one of the lower limits, equal to or less than any one of the upper limits, or within a range between any one of the lower limits and any one of the upper limits.

[0247] The present invention also relates to a thermal interface material (TIM), which may be a cured product of the resin composition.

[0248] Therefore, the thermal interface material may also exhibit the aforementioned adhesion to aluminum and polyester, thermal conductivity, hardness, bend radius, electrical insulation, flame retardancy, specific gravity, shrinkage rate, thermal expansion coefficient, and / or 5% weight loss temperature in thermogravimetric analysis (TGA).

[0249] Thus, the thermal interface material may include components contained in the resin composition or components derived from those components.

[0250] For example, when the resin composition is a polyurethane composition, the thermal interface material may include the polyurethane.

[0251] Polyurethanes can be formed by the reaction of the reactive compounds described above with a curing agent (polyisocyanate).

[0252] Therefore, the polyurethane may contain units derived from the reactive compound.

[0253] For example, when the reactive compound includes the aforementioned polyester backbone (e.g., polycaprolactone backbone) or polyether backbone (e.g., polyalkylene backbone), the polyurethane may include the polyester unit (e.g., polycaprolactone unit) or polyether unit (e.g., polyalkylene unit).

[0254] For example, the polyurethane may include units of formulas 2, 3, 5 and / or 6 shown above.

[0255] The polyurethane may also contain a hydrocarbon group derived from the oil-modified compound described above, that is, a straight-chain or branched-chain hydrocarbon group having three or more carbon atoms.

[0256] As described above, the lower limit of the number of carbon atoms in the linear or branched hydrocarbon group may be about 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, or 17, and the upper limit may be about 50, 49, 48, 47, 46, 45, 44, 43, 42, 41, The number of carbon atoms may be about 40, 39, 38, 37, 36, 35, 34, 33, 32, 31, 30, 29, 28, 27, 26, 25, 24, 23, 22, 21, 20, 19, 18, 17, 16, 15, 14, 13, 12, 11, 10, 9, or 8. The number of carbon atoms may be equal to or less than any one of the above upper limits, equal to or greater than any one of the above lower limits, or within a range between any one of the above lower limits and any one of the above upper limits.

[0257] The linear or branched hydrocarbon group may or may not contain a double bond. If it contains a double bond, the double bond may be a conjugated double bond or a cis double bond.

[0258] Specific examples of the hydrocarbon group include an alkyl group, an alkenyl group, and an alkynyl group. In one example, the hydrocarbon group may be linked to the polyurethane skeleton via a carbonyl group or a carbonyloxy group, in which case the hydrocarbon group may be an alkylcarbonyl group, an alkenylcarbonyl group, an alkynylcarbonyl group, an alkylcarbonyloxy group, an alkenylcarbonyloxy group, or an alkynylcarbonyloxy group. In the above, the number of carbon atoms in the alkyl group, alkenyl group, or alkynyl group may be equal to or greater than any one of the lower limits of the number of carbon atoms in the linear or branched hydrocarbon group, equal to or less than any one of the upper limits of the number of carbon atoms in the linear or branched hydrocarbon group, or may be within a range between any one of the lower limits of the number of carbon atoms in the linear or branched hydrocarbon group and any one of the upper limits of the number of carbon atoms in the linear or branched hydrocarbon group.

[0259] The alkyl group, alkenyl group, or alkynyl group may be linear or branched, and may be optionally substituted with one substituent. When a substituent is present, the type of the substituent is not particularly limited, and examples of the substituent include a halogen atom such as fluorine.

[0260] As mentioned above, the hydrocarbon group may be included in the structures of the chemical formulas 1 to 6 mentioned above.

[0261] Furthermore, the polyurethane may contain units derived from the curable component described above, and therefore may contain units of the first reactive compound and units of the second reactive compound, or may contain units of the third reactive compound and units of the fourth reactive compound as units of the second reactive compound.

[0262] The specific details of the reactive compounds and the ratios therebetween can be applied in the same manner as those described in the resin composition.

[0263] In addition, the polyurethane may contain units derived from the curing agent, and therefore may contain the polyisocyanate units described above, for example, tri- or higher functional polyisocyanate units and bifunctional polyisocyanate units. Specific descriptions of the polyisocyanates and their ratios are the same as those described in the resin composition.

[0264] The polyurethane contained in the thermal interface material may contain at least one hydroxy group. That is, polyurethane can be synthesized by forming a urethane bond through the reaction of the hydroxy group of the reactive compound with the isocyanate group of the polyisocyanate curing agent. By adjusting the hydroxy group equivalent of the reactive compound during this process, at least one hydroxy group can remain in the final polyurethane. For example, the polyurethane may contain hydroxy groups in an amount of 0.1 mol / g or more, 0.1 mol / g to 10 mol / g, 0.1 mol / g to 9 mol / g, 0.1 mol / g to 8 mol / g, 0.1 mol / g to 7 mol / g, 0.1 mol / g to 6 mol / g, 0.1 mol / g to 5 mol / g, 0.1 mol / g to 4 mol / g, 0.1 mol / g to 3 mol / g, 0.1 mol / g to 2 mol / g, 0.1 mol / g to 1 mol / g, or 0.1 mol / g to 0.5 mol / g. By leaving hydroxyl groups in the polyurethane at the above ratio, it is possible to more effectively form a thermal interface material with the desired properties. There are no particular limitations on the method for leaving hydroxyl groups in the polyurethane, and the above polyurethane can be formed by adjusting the OH / NCO equivalent ratio during the reaction process.

[0265] The thermal interface material may contain the components of the resin composition described above, such as a curing rate modifier, a plasticizer, a catalyst, and / or a filler, along with the polyurethane. The specific components and weight ratios thereof may be the same as those described for the resin composition.

[0266] The present invention also relates to a product comprising the resin composition or its cured product (thermal interface material or heat transfer material). The resin composition of the present invention or its cured product can be usefully applied as a heat dissipation material. Therefore, the product may include a heat-generating component. The term "heat-generating component" refers to a component that generates heat during use, and the type of component is not particularly limited. Representative heat-generating components include various electrical / electronic products, including battery cells, battery modules, and battery packs.

[0267] The product of the present invention may include, for example, the heat-generating component, and the resin composition (or the two-component composition) or a cured product thereof that is present adjacent to the heat-generating component.

[0268] The specific method for constructing the product of the present invention is not particularly limited, and when the resin composition or two-component composition of the present invention or its cured product is applied to a heat dissipation material, the product can be constructed using various known methods. [Effects of the Invention]

[0269] The present invention provides a curable composition, a thermal interface material (TIM), and uses thereof. The curable composition or thermal interface material exhibits high thermal conductivity while exhibiting low adhesive strength to a specific substrate. Furthermore, the low adhesive strength can be achieved without using adhesive strength control ingredients such as plasticizers, or by minimizing their use.

[0270] The present invention also enables the curable composition to exhibit a precisely controlled cure rate while at the same time having excellent curability.

[0271] The present invention can also provide a product containing the curable composition, its cured product, or a thermal interface material. [Brief explanation of the drawings]

[0272] [Figure 1]FIG. 1 is a diagram showing a device for measuring a load value. [Figure 2] FIG. 2 shows the analysis results of the reactive compound synthesized in Production Example 1. [Figure 3] FIG. 3 shows the analysis results of the reactive compound synthesized in Production Example 2. [Figure 4] FIG. 4 is a graph recording the change in viscosity over time. [Figure 5] FIG. 5 is a graph recording the change in hardness over time. DETAILED DESCRIPTION OF THE INVENTION

[0273] The present invention will be described in detail below with reference to examples, but the scope of the present invention is not limited to the following examples.

[0274] The cured products mentioned below were formed by mixing the main component and the curing component of the resin composition of the examples, which were manufactured as a two-component type, so as to satisfy the OH / NCO equivalent ratio described in each example, and then maintaining the mixture at room temperature (approximately 25°C) for approximately 24 hours.

[0275] In the examples, the physical properties were evaluated by the following methods.

[0276] 1. Thermal conductivity The thermal conductivity of the resin composition (curable composition) or its cured product was measured using the hot-disk method in accordance with ISO 22007-2. Specifically, a mixture of the base resin and curing agent components of the examples or comparative examples in a 1:1 volume ratio was placed in a mold approximately 7 mm thick, and the thermal conductivity was measured in the through-plane direction using a hot-disk device. As specified in ISO 22007-2, a hot-disk device is a device that can determine thermal conductivity by measuring temperature changes (electrical resistance changes) when a sensor with a double-spiral nickel wire is heated, and thermal conductivity was measured according to this standard.

[0277] 2. Measurement of adhesive strength to polyester The adhesive strength to polyester was evaluated using a test specimen prepared by adhering a polyethylene terephthalate (PET) film to an aluminum plate. The PET film was approximately 10 mm wide and 200 mm long, and the aluminum plate was 100 mm wide and 100 mm long. A resin composition was applied to the entire surface of the aluminum plate, and the PET film was attached to the resin composition. This was maintained at room temperature (approximately 25°C) for approximately 24 hours to prepare a test specimen. The entire width and approximately 100 mm of the length of the PET film were attached to the aluminum plate via the resin composition. The adhesive strength was measured by peeling the PET film from the aluminum plate in the length direction while the aluminum plate of the test specimen was fixed. The adhesion was performed by applying a resin composition (a mixture of base and hardener parts in a volume ratio of 1:1) to the aluminum plate so that the thickness after curing was about 2 mm, then adhering the PET film to the resin composition layer and maintaining it at room temperature (about 25°C) for about 24 hours to cure the resin composition. The peeling was performed at a peeling speed of about 0.5 mm / min and a peeling angle of 180° until the PET film was completely peeled off.

[0278] 3. Measurement of adhesion strength to aluminum An uncured resin composition (a mixture of base and curing agent parts in a 1:1 volume ratio) was coated onto the center of an aluminum substrate measuring 2 cm in width and 7 cm in length, covering an area of ​​approximately 2 cm in width and 2 cm in length. An aluminum substrate measuring 2 cm in width and 7 cm in length was then attached to the coating layer and maintained in this state while the resin composition was cured. The two aluminum substrates were attached at a 90-degree angle to each other. The upper aluminum substrate was then fixed, and the lower aluminum substrate was pressed against the upper aluminum substrate at a speed of 0.5 mm / min. The force required for the separation of the lower aluminum substrate was measured. The maximum force measured during this process was divided by the area of ​​the test specimen to determine the adhesion strength to aluminum.

[0279] 4. Hardness measurement The hardness of the cured resin composition was measured according to ASTM D 2240 and JIS K 6253. The hardness was measured using an ASKER durometer hardness instrument by applying a load of 1 kg or more (approximately 1.5 kg) to the surface of a flat sample (cured product) to measure the initial hardness, and the stabilized measurement value was checked after 15 seconds to evaluate the hardness.

[0280] 5. Viscosity Measurement The viscosity was measured at room temperature (approximately 25°C) using a Brookfield HB DB3T type instrument at 0.01s. -1 ~10.0s -1 The viscosity was measured at a shear rate of up to 2.4 s unless otherwise specified. -1 is the viscosity at the point

[0281] 6. Measurement of hardening speed (time to confirm hardness) The curing rate of the resin composition was evaluated based on the change in hardness over time. Hardness was measured according to ASTM D 2240 and JIS K 6253, as described above. The base resin and hardener were mixed in a 1:1 volume ratio and maintained at room temperature (approximately 25°C). The hardness was measured every 30 minutes. The curing rate was evaluated based on the time at which Shore 00 hardness was first detected.

[0282] 7. Measurement of curing speed (time to increase viscosity) The cure rate of the resin composition was also evaluated through the change in viscosity over time.

[0283] Specifically, V1 in the following formula 1 was confirmed and the curing rate was evaluated.

[0284] [Formula 1] V1=V initial / t

[0285] In equation 1, V initialis the initial viscosity (unit: cps) of a mixture obtained by mixing the curable composition with a curing agent component having a polyisocyanate, and t is the time (unit: minutes) required for the viscosity of the mixture to double compared to the initial viscosity.

[0286] Specifically, the V initial The base resin part and the hardener part prepared in the examples or comparative examples were mixed in a volume ratio of 1:1, and the mixture was loaded into a viscosity measuring device (Brookfield HB DB3T type device) and the viscosity was measured at 2.4 s. -1 The shear rate was maintained for approximately 60 seconds, and the viscosity was measured after stabilizing.

[0287] The viscosity was measured by loading the solution into a Brookfield HB DB3T type viscometer at a shear rate of 2.4 s -1 Measurements were taken over time while maintaining the conditions.

[0288] 8. Bending radius measurement The bending radius of the cured product was evaluated using cured products with width, length, and thickness of 1 cm, 10 cm, and 2 mm, respectively. The bending radius was determined by attaching the cured product to cylinders of various radii and bending the cured product in the vertical direction. The bending radius was determined by measuring the minimum radius of the cylinder at which the cured product did not crack.

[0289] 9. Measurement of average particle size The average particle size of a filler is the D50 particle size of the filler, which is measured using a Marvern MASTERSIZER 3000 device in accordance with ISO-13320. Ethanol was used as the solvent during measurement. The incident laser is scattered by the filler dispersed in the solvent, and the intensity and directionality of the scattered laser vary depending on the size of the filler. The D50 particle size can be determined by analyzing this using Mie theory. Through this analysis, the distribution is determined by converting it to the diameter of a sphere having the same volume as the dispersed filler, and the D50 value, which is the median value of the distribution, can be obtained to evaluate the particle size.

[0290] 10. Evaluation of module workability The resin composition (a mixture of base and hardener parts in a 1:1 volume ratio) was applied to an aluminum plate in the shape of a regular square measuring 8 cm in width and length, with a thickness of approximately 2 mm, and was then cured for approximately 24 hours at room temperature (approximately 25°C) and room humidity (approximately 40% relative humidity). Next, the cured product was peeled off from the aluminum plate, and the module workability was evaluated according to the following criteria.

[0291] <Evaluation criteria> ○: The cured resin composition peels off in sheets from the aluminum plate without leaving any residue. ×: The cured resin composition was impossible to peel off from the aluminum plate, or residue remained even after peeling.

[0292] 11.Evaluating Purging Latency The purging waiting time was evaluated by measuring the load value.

[0293] The load value (unit: kgf) was evaluated using an apparatus as shown in Figure 1. The apparatus in Figure 1 is an apparatus 1 in which two cartridges 2, 2a, and 2b and one static mixer 5 are connected. The cartridges 2, 2a, and 2b in the apparatus 1 were cartridges (Sulzer, AB050-01-10-01) with a material inlet port having a circular shape with a diameter of 18 mm, and material outlet ports 4, 4a, and 4b having a circular shape with a diameter of 3 mm, a height of 100 mm, and an internal volume of 25 ml. The static mixer 5 was a stepped static mixer (Sulzer, MBH-06-16T) with a circular outlet port 7 having a diameter of 2 mm and 16 elements. A texture analyzer (TA) was used as the pressurizing means 3, 3a, and 3b (means for extruding the composition loaded into the cartridge) of the apparatus.

[0294] For the measurement of the load value, the main agent part was loaded into one of the two cartridges 2a and 2b, and the curing agent part was loaded into the other cartridge. Next, it was pressurized at a constant speed of 1 mm / sec by the pressurizing means 3, 3a, and 3b, and the main agent and the curing agent parts were injected into the static mixer 5, mixed by the mixer 5, and discharged from the discharge part 7. The force applied to the pressurizing means from the start of pressurization by the pressurizing means until the discharge was measured in the above process. The maximum value of the force applied to the pressurizing means in the above process was taken as the load value.

[0295] After measuring the load value, the pressurization was interrupted, and the apparatus 1 was maintained at room temperature (about 25°C). In such a case, the mixture of the main agent part and the curing agent part was maintained in the mixer 5. After waiting for a certain period of time, the pressurization was started again by the pressurizing means, and the load value was measured in the same manner as above. The waiting time when the load value reached 60 kgf in this process was taken as the purging waiting time.

[0296] 12. Measurement of weight average molecular weight The weight average molecular weight (Mw) was measured using GPC (Gel permeation chromatography). Specifically, for the weight average molecular weight (Mw), the sample to be analyzed was placed in a 5 mL vial, diluted with a THF (tetrahydrofuran) solvent to a concentration of about 1 mg / mL, and then the calibration standard sample and the analysis sample were filtered through a syringe filter (pore size: 0.45 μm) and measured. As the analysis program, ChemStation of Agilent technologies was used, and the weight average molecular weight (Mw) could be obtained by comparing the elution time of the sample with the calibration curve.

[0297] <GPC measurement conditions> Equipment: 1200 series of Agilent technologies Column: TL Mix.A&B of Agilent technologies was used Solvent: THF (tetrahydrofuran) Column temperature: 35 °C Sample concentration: 1 mg / mL, 200 μL injection Standard sample: Polystyrene (MP: 3900000, 723000, 316500, 52200, 31400, 7200, 3940, 485) was used

[0298] 13. GC-MS (Gas Chromatography-Mass Spectrometry) analysis As the measuring instrument for GC-MS analysis, an instrument of Agilent was used (GC (Gas Chromatography) instrument: 7890 model, MS (Mass Spectrometry) Detector: 5977B model). The sample (the cured product of the resin composition) was dissolved in a solvent (chloroform) at a concentration of 100 mg / mL, the supernatant was extracted, filtered through a 0.2-μm syringe filter, and then loaded onto the GS-MS analysis instrument. The analysis was carried out under the following conditions, and quantitative analysis was carried out through the intensity of the peaks of the target substances to be detected (1-dodecanethiol and 2-ethylhexanoic acid).

[0299] <GC measurement conditions> Column: HP-5MS of Agilent technologies Gas flow rate: Column (He): 1 mL / min Ionization mode: EI Injection temperature: 300 °C Injection volume: 0.5 μL

[0300] Production Example 1. The oil-modified compound (reactive compound) of the following chemical formula A was produced in the following manner.

[0301]

Chemical formula

[0302] In chemical formula A, n and m are each greater than 0, and the sum (n+m) is approximately 4.8.

[0303] Polycaprolactone polyol (Perstorp, Capa 3031) and the saturated fatty acid isononanoic acid were mixed in a weight ratio of 1:0.53 (Capa 3031:isononanoic acid). Next, 0.1 parts by weight of a catalyst (Tin(II) 2-ethylhexanoate (Sigma-Aldrich)) was added per 100 parts by weight of the mixture, and the mixture was stirred and maintained at 150°C for 30 minutes under an inert gas purge. A small amount of xylene, an azeotropic solution, was then added, and the temperature was raised to 200°C. The reaction was continued for at least 3 hours, after which the pressure was reduced to below 80 Torr and the xylene and unreacted materials were removed. The reaction mixture was cooled and filtered to obtain the target product (compound of formula A).

[0304] The GPC analysis of the target product showed that the weight average molecular weight was at a level of about 710 g / mol. Figure 2 shows the results of the GPC analysis of the target product.

[0305] Production example 2. The oil-modifying compound (reactive compound) of the following chemical formula B was prepared in the following manner.

[0306] [ka]

[0307] In chemical formula B, p and q are each greater than 0, and the sum (p+q) is approximately 4.8.

[0308] Polycaprolactone polyol (Perstorp Capa 3031) and the saturated fatty acid isononanoic acid were mixed in a weight ratio of 1:1.06 (Capa 3031:isononanoic acid). Next, 0.1 parts by weight of a catalyst (Tin(II) 2-ethylhexanoate (Sigma-Aldrich)) was added per 100 parts by weight of the mixture, and the mixture was stirred and maintained at 150°C for 30 minutes under an inert gas purge. A small amount of xylene, an azeotropic solution, was then added, and the temperature was raised to 200°C. The reaction was continued for at least 3 hours, after which the pressure was reduced to below 80 Torr and the xylene and unreacted materials were removed. The reaction mixture was cooled and filtered to obtain the target product (compound of formula B).

[0309] The GPC analysis of the target product showed that the weight average molecular weight was at a level of about 814 g / mol. Figure 3 shows the results of the GPC analysis of the target product.

[0310] Example 1 Manufacturing of base parts The oil-modified compounds of Production Examples 1 and 2, a non-oil-modified compound (Kuraray, F-2010), a urethane reaction catalyst (DBTDL, dibutyltin dilaurate), a thiol compound (1-dodecanethiol), a carboxylic acid compound (2-EHA, 2-ethylhexanoic acid), a filler component, and a plasticizer (diisononyl adipate) were mixed in a weight ratio of 4.59:5.1:0.51:0.066:0.2:0.066:88.8:0.71 (Production Example 1: Production Example 2: F-2010:DBTDL:thiol:2-EHA:filler:plasticizer) to produce a base part. The filler component was prepared by mixing a first alumina filler having an average particle size of approximately 70 μm, a second alumina filler having an average particle size of approximately 20 μm, and a third alumina filler having an average particle size of approximately 1 μm, in a volume ratio of approximately 6:2:2 (first alumina filler:second alumina filler:third alumina filler).

[0311] Hardener part manufacturing Polyisocyanate (Tolonate HDT-LV2, manufactured by Vencorex) was used as the curing agent. The polyisocyanate, filler component, and plasticizer (diisononyl adipate) were mixed in a weight ratio of 5.08:4.78:90.1 (polyisocyanate:filler:plasticizer) to produce the cured part. The filler component was produced by mixing a first alumina filler with an average particle size of approximately 70 μm, a second alumina filler with an average particle size of approximately 20 μm, and a third alumina filler with an average particle size of approximately 1 μm. The volume ratio during mixing was approximately 6:2:2 (first alumina filler:second alumina filler:third alumina filler).

[0312] The curing agent part was prepared so that when the curing agent part was mixed with the base part in a volume ratio of 1:1, the equivalent ratio (OH / NCO) of the hydroxyl groups (OH) present in the base part to the isocyanate groups (NCO) present in the curing agent part was approximately 100.

[0313] Production of resin composition and cured product The base material and the curing agent parts were prepared separately to prepare a resin composition (curable composition), and the base material and the curing agent parts were mixed in a volume ratio of about 1:1, and then maintained at room temperature (about 25°C) to form a cured product.

[0314] Example 2. The base part was prepared in the same manner as in Example 1, except that the weight ratio of the oil-modified compound, non-oil-modified compound (Kuraray, F-2010), urethane reaction catalyst (DBTDL, dibutyltin dilaurate), thiol compound (1-dodecanethiol), carboxylic acid compound (2-EHA, 2-ethylhexanoic acid), filler component, and plasticizer (diisononyl adipate) in Preparation Examples 1 and 2 was changed to 4.59:5.1:0.51:0.048:0.096:0.096:88.9:0.71 (Preparation Example 1: Preparation Example 2: F-2010:DBTDL:thiol:2-EHA:filler:plasticizer). The curing agent part, resin composition, and cured product were prepared in the same manner as in Example 1.

[0315] Example 3. The base part was prepared in the same manner as in Example 1, except that the weight ratio of the oil-modified compound, non-oil-modified compound (Kuraray, F-2010), urethane reaction catalyst (DBTDL, dibutyltin dilaurate), thiol compound (1-dodecanethiol), carboxylic acid compound (2-EHA, 2-ethylhexanoic acid), filler component, and plasticizer (diisononyl adipate) in Preparation Examples 1 and 2 was changed to 4.59:5.1:0.51:0.06:0.11:0.11:88.8:0.71 (Preparation Example 1: Preparation Example 2: F-2010:DBTDL:thiol:2-EHA:filler:plasticizer). The curing agent part, resin composition, and cured product were prepared in the same manner as in Example 1.

[0316] Example 4. The oil-modified compounds of Preparation Examples 1 and 2, a non-oil-modified compound (Kuraray F-2010), a urethane reaction catalyst (DBTDL, dibutyltin dilaurate), a thiol compound (1-dodecanethiol), a carboxylic acid compound (2-EHA, 2-ethylhexanoic acid), a filler component, and a plasticizer (diisononyl adipate) were blended in a weight ratio of 4.59:5.1:0.51:0.03:0.055:0.055:89:0.71 (Preparation Example 1: Preparation Example 2: F-2010:DBTDL:thiol:2-EHA:filler:plasticizer) to produce a base part. The filler component was the same as in Example 1.

[0317] The curing agent part, resin composition and cured product were prepared in the same manner as in Example 1.

[0318] Example 5. The oil-modified compounds of Preparation Examples 1 and 2, a non-oil-modified compound (Kuraray F-2010), a urethane reaction catalyst (DBTDL, dibutyltin dilaurate), a thiol compound (1-dodecanethiol), a carboxylic acid compound (2-EHA, 2-ethylhexanoic acid), a filler component, and a plasticizer (diisononyl adipate) were blended in a weight ratio of 4.59:5.1:0.51:0.018:0.033:0.033:89:0.71 (Preparation Example 1: Preparation Example 2: F-2010:DBTDL:thiol:2-EHA:filler:plasticizer) to produce a base part. The filler component was the same as in Example 1.

[0319] The curing agent part, resin composition and cured product were prepared in the same manner as in Example 1.

[0320] Example 6 The oil-modified compounds of Preparation Examples 1 and 2, a non-oil-modified compound (Kuraray F-2010), a urethane reaction catalyst (DBTDL, dibutyltin dilaurate), a thiol compound (1-dodecanethiol), a carboxylic acid compound (2-EHA, 2-ethylhexanoic acid), a filler component, and a plasticizer (diisononyl adipate) were blended in a weight ratio of 4.59:5.11:0.51:0.012:0.022:0.022:89:0.71 (Preparation Example 1: Preparation Example 2: F-2010:DBTDL:thiol:2-EHA:filler:plasticizer) to produce a base part. The filler component was the same as in Example 1.

[0321] The curing agent part, resin composition and cured product were prepared in the same manner as in Example 1.

[0322] Example 7 The oil-modified compounds of Preparation Examples 1 and 2, a non-oil-modified compound (Kuraray F-2010), a urethane reaction catalyst (DBTDL, dibutyltin dilaurate), a thiol compound (1-dodecanethiol), a carboxylic acid compound (2-EHA, 2-ethylhexanoic acid), a filler component, and a plasticizer (diisononyl adipate) were blended in a weight ratio of 4.6:5.11:0.51:0.0066:0.011:0.011:89:0.71 (Preparation Example 1: Preparation Example 2: F-2010:DBTDL:thiol:2-EHA:filler:plasticizer) to produce a base part. The filler component was the same as in Example 1.

[0323] The curing agent part, resin composition and cured product were prepared in the same manner as in Example 1.

[0324] Comparative Example 1 The base part, the curing agent part, the resin composition, and the cured product were prepared in the same manner as in Example 1, except that the thiol compound and the carboxylic acid compound were not used in preparing the base part.

[0325] Comparative Example 2 The base part was prepared in the same manner as in Example 1, except that the blending weight ratio of the oil-modified compound, non-oil-modified compound (Kuraray, F-2010), urethane reaction catalyst (DBTDL, dibutyltin dilaurate), carboxylic acid compound (2-EHA, 2-ethylhexanoic acid), filler component, and plasticizer (diisononyl adipate) in Preparation Examples 1 and 2 was changed to 4.59:5.10:0.51:0.066:0.13:88.9:0.71 (Preparation Example 1: Preparation Example 2: F-2010:DBTDL:2-EHA:filler:plasticizer). The curing agent part, resin composition, and cured product were prepared in the same manner as in Example 1.

[0326] Comparative Example 3. The base part was prepared in the same manner as in Example 1, except that the blending weight ratio of the oil-modified compound, non-oil-modified compound (Kuraray, F-2010), urethane reaction catalyst (DBTDL, dibutyltin dilaurate), thiol compound (1-dodecanethiol), filler component, and plasticizer (diisononyl adipate) in Preparation Examples 1 and 2 was changed to 4.59:5.1:0.51:0.066:0.13:88.9:0.71 (Preparation Example 1: Preparation Example 2: F-2010:DBTDL:thiol:filler:plasticizer). The curing agent part, resin composition, and cured product were prepared in the same manner as in Example 1.

[0327] Comparative Example 4. The base part was prepared in the same manner as in Example 1, except that the weight ratio of the oil-modified compound, non-oil-modified compound (Kuraray, F-2010), urethane reaction catalyst (DBTDL, dibutyltin dilaurate), thiol compound (1-dodecanethiol), filler component, and plasticizer (diisononyl adipate) in Preparation Examples 1 and 2 was changed to 4.59:5.1:0.51:0.066:0.153:88.9:0.71 (Preparation Example 1: Preparation Example 2: F-2010:DBTDL:thiol:filler:plasticizer). The curing agent part, resin composition, and cured product were prepared in the same manner as in Example 1.

[0328] Comparative Example 5. The base part was prepared in the same manner as in Example 1, except that the blending weight ratio of the oil-modified compound, non-oil-modified compound (Kuraray, F-2010), urethane reaction catalyst (DBTDL, dibutyltin dilaurate), thiol compound (1-dodecanethiol), filler component, and plasticizer (diisononyl adipate) in Preparation Examples 1 and 2 was changed to 4.59:5.1:0.51:0.066:0.2:88.8:0.71 (Preparation Example 1: Preparation Example 2: F-2010:DBTDL:thiol:filler:plasticizer). The curing agent part, resin composition, and cured product were prepared in the same manner as in Example 1.

[0329] Comparative Example 6. The base part was prepared in the same manner as in Example 1, except that the blending weight ratio of the oil-modified compound, non-oil-modified compound (Kuraray, F-2010), urethane reaction catalyst (DBTDL, dibutyltin dilaurate), filler component, and plasticizer (diisononyl adipate) in Preparation Examples 1 and 2 was changed to 4.6:5.11:0.51:0.048:89:0.71 (Preparation Example 1: Preparation Example 2: F-2010:DBTDL:filler:plasticizer). The curing agent part, resin composition, and cured product were prepared in the same manner as in Example 1.

[0330] Comparative Example 7. The base part was prepared in the same manner as in Example 1, except that the blending weight ratio of the oil-modified compound, non-oil-modified compound (Kuraray, F-2010), urethane reaction catalyst (DBTDL, dibutyltin dilaurate), thiol compound (1-dodecanethiol), filler component, and plasticizer (diisononyl adipate) in Preparation Examples 1 and 2 was changed to 4.59:5.1:0.51:0.048:0.096:89:0.71 (Preparation Example 1: Preparation Example 2: F-2010:DBTDL:thiol:filler:plasticizer). The curing agent part, resin composition, and cured product were prepared in the same manner as in Example 1.

[0331] Comparative Example 8. The base part was prepared in the same manner as in Example 1, except that the blending weight ratio of the oil-modified compound, non-oil-modified compound (Kuraray, F-2010), urethane reaction catalyst (DBTDL, dibutyltin dilaurate), carboxylic acid compound (2-EHA, 2-ethylhexanoic acid), filler component, and plasticizer (diisononyl adipate) in Preparation Examples 1 and 2 was changed to 4.59:5.1:0.51:0.048:0.096:89:0.71 (Preparation Example 1: Preparation Example 2: F-2010:DBTDL:2-EHA:filler:plasticizer). The curing agent part, resin composition, and cured product were prepared in the same manner as in Example 1.

[0332] Comparative Example 9. The base part was prepared in the same manner as in Example 1, except that the blending weight ratio of the oil-modified compound, non-oil-modified compound (Kuraray, F-2010), urethane reaction catalyst (DBTDL, dibutyltin dilaurate), thiol compound (1-dodecanethiol), filler component, and plasticizer (diisononyl adipate) in Preparation Examples 1 and 2 was changed to 4.59:5.1:0.51:0.06:0.11:88.9:0.71 (Preparation Example 1: Preparation Example 2: F-2010:DBTDL:thiol:filler:plasticizer). The curing agent part, resin composition, and cured product were prepared in the same manner as in Example 1.

[0333] Comparative Example 10. The base part was prepared in the same manner as in Example 1, except that the weight ratio of the oil-modified compound, non-oil-modified compound (Kuraray, F-2010), urethane reaction catalyst (DBTDL, dibutyltin dilaurate), carboxylic acid compound (2-EHA, 2-ethylhexanoic acid), filler component, and plasticizer (diisononyl adipate) in Preparation Examples 1 and 2 was changed to 4.59:5.10:0.51:0.060:0.11:88.9:0.71 (Preparation Example 1: Preparation Example 2: F-2010:DBTDL:2-EHA:filler:plasticizer). The curing agent part, resin composition, and cured product were prepared in the same manner as in Example 1.

[0334] The physical property evaluation results for each of the examples and comparative examples are shown in the following Tables 1 to 4. In the following Tables 1 and 2, the hardness (Shore 00 and Shore A hardness) is the hardness measured after maintaining a mixture of the base part and the hardener part in a 1:1 volume ratio at room temperature (about 25°C) for 24 hours.

[0335] In Tables 1 to 4 below, the curing speed (hardness) is the time (unit: hours) at which Shore 00 hardness is first confirmed when the base part and hardener part of the example or comparative example are mixed in a 1:1 volume ratio, maintained at room temperature (approximately 25°C), and the hardness is checked every 30 minutes (related to Measurement 6. Measurement of curing speed (time to check hardness) above).

[0336] In Tables 1 to 4 below, the curing speed (viscosity) is the curing speed measurement method (viscosity increase time) where t (unit: minutes) in Equation 1 is V initial and V1 are V in the above formula 1, respectively. initial and V1.

[0337] [Table 1]

[0338] [Table 2]

[0339] [Table 3]

[0340] [Table 4]

[0341] Test example 1. To confirm the cure retardation effect due to the action of the thiol compound and the carboxylic acid compound, evaluations were carried out on the resin compositions of Example 1 and Comparative Examples 1, 2, and 5. The base part and curing agent part of the resin composition of each of the Examples or Comparative Examples were mixed in a volume ratio of 1:1, and the changes in viscosity and hardness over time were evaluated. The results are shown in Figures 4 and 5.

[0342] Referring to the drawing, in the case of Example 1, which contains both a thiol compound and a carboxylic acid compound, a viscosity maintenance section is observed in which the viscosity after mixing is maintained, and after the viscosity maintenance section, the viscosity rapidly increases, and after the curing delay, the curing property is stably secured. Also, from the viewpoint of hardness, it is observed that there is a section in which the hardness is not measured for an appropriate time.

[0343] It can be seen that the viscosity of Comparative Example 1, which does not contain a thiol compound or a carboxylic acid compound, increases rapidly immediately after mixing the base and hardener parts, and the hardness also begins to increase at an early stage immediately after mixing.

[0344] In the case of Comparative Example 2 containing only a carboxylic acid compound, the viscosity increased more slowly than in Comparative Example 1, but there was no viscosity maintenance period in which the viscosity was maintained constant at the initial stage of mixing, and hardness was observed excessively slowly, and the viscosity did not increase well over time, indicating insufficient curability.

[0345] In Comparative Example 5, which contained only a thiol compound, a viscosity maintenance period was observed, but it was relatively short, and the viscosity increased excessively quickly after the viscosity maintenance period. Furthermore, in Comparative Example 5, the hardness also increased excessively rapidly, which suggests that it may be difficult to ensure sufficient working time in large-area coating processes.

[0346] Test example 2. Table 5 below summarizes the contents of thiol compounds and carboxylic acid compounds in the base resin parts and cured products of Examples 2 to 7.

[0347] In Table 5 below, the blending amount is the amount (unit: wt%) of the thiol compound and carboxylic acid compound added during production, and the detected amount is the amount (unit: wt%) detected by GC-MS (Gas Chromatography-Mass Spectrometry) analysis.

[0348] The results in Table 5 show that the thiol and carboxylic acid compounds added to the base part remain in the cured body after the curing reaction. In Examples 4 to 7, there were cases where the thiol and / or carboxylic acid compounds were not detected, but this was due to the small amount added. Considering the results in Examples 2 and 3, it can be inferred that the carboxylic acid and thiol compounds are also present in the cured bodies of Examples 4 to 7.

[0349] [Table 5]

Claims

1. a curable component comprising a reactive compound having a hydroxy group; thiol compounds, carboxylic acid compounds, Urethane reaction catalyst and A curable composition comprising a filler component.

2. The curable composition of claim 1 , wherein the curable component comprises a first reactive compound having one hydroxy group and a second reactive compound having two or more hydroxy groups.

3. The curable composition according to claim 2, wherein the second reactive compound having two or more hydroxy groups comprises a third reactive compound having two hydroxy groups and a fourth reactive compound having three or more hydroxy groups.

4. The curable composition according to claim 1 , wherein the reactive compound contains a branched hydrocarbon chain having 5 or more carbon atoms at its terminal end.

5. The curable composition according to claim 3 , wherein the first and third reactive compounds each contain a branched hydrocarbon chain having 5 or more carbon atoms at the end thereof.

6. The curable composition of claim 3 , wherein the fourth reactive compound comprises polycaprolactone polyol units or alkanediol units; polyol units and dicarboxylic acid units.

7. The curable composition according to claim 1 , wherein the thiol compound is a monofunctional compound having a hydrocarbon group.

8. The curable composition according to claim 7, wherein the monofunctional compound has a molecular weight in the range of 50 to 400 g / mol.

9. The curable composition according to claim 1, wherein the thiol compound is contained in an amount of 0.5 to 10 parts by weight per 100 parts by weight of the curable component.

10. The curable composition according to claim 1 , wherein the carboxylic acid compound is a monofunctional compound having a hydrocarbon group.

11. The curable composition according to claim 10, wherein the monofunctional compound has a molecular weight in the range of 50 to 400 g / mol.

12. The curable composition according to claim 1, wherein the carboxylic acid compound has a pKa in the range of 2 to 9.

13. The curable composition according to claim 1, wherein the carboxylic acid compound is contained in an amount of 0.1 to 3 parts by weight based on 100 parts by weight of the curable component.

14. The curable composition of claim 1 , wherein the urethane reaction catalyst is a tin catalyst.

15. The curable composition according to claim 1, wherein the weight ratio of the thiol compound to the carboxylic acid compound is in the range of 1 to 5.

16. 2. The curable composition according to claim 1, wherein the weight ratio of the thiol compound to the urethane reaction catalyst is in the range of 1 to 5.

17. The curable composition according to claim 1 , which forms a cured product having a thermal conductivity of 2.0 W / mK or more.

18. Adhesion strength to aluminum is 0.15 N / mm ２ The curable composition according to claim 1 , which forms the following cured product:

19. The curable composition according to claim 1 , which forms a cured product having an adhesive strength to polyester of 100 gf / cm or less.

20. The curable composition according to claim 1 , which forms a cured product having a Shore OO hardness of 95 or less.

21. The curable composition of claim 1 further comprising a plasticizer.

22. The curable composition according to claim 1 , comprising 500 parts by weight or more of the filler component per 100 parts by weight of the curable component.

23. A two-component composition comprising a base part and a hardener part, A two-component composition, wherein the main component is the curable composition according to any one of claims 1 to 22.

24. 24. The two-part composition of claim 23, wherein the hardener part comprises a polyisocyanate compound and a filler component.

25. a heating element and a thermally conductive material adjacent to the heating element; 24. A product comprising the thermally conductive material comprising the curable composition of claim 1 or the cured product of the two-component composition of claim 23.

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