Hardening components

Abstract

The present application relates to a resin composition or its use. The present application may provide a resin composition or its cured product that exhibits high thermal conductivity and low adhesive strength to a specific adherend. The present application may also achieve the low adhesive strength without using an adhesive strength adjusting component such as a plasticizer, or with the proportion of such a component minimized. The present application may further provide a product including the curable composition or its cured product.

Description

[Technical Field]

[0001] This application relates to a curable composition. [Background technology]

[0002] With the increasing number of electrical or electronic devices that require heat management, such as batteries, the importance of heat dissipation materials is growing.

[0003] Various types of heat dissipation materials are known. One conventional heat dissipation material is one in which a heat-dissipating filler is filled into a resin binder (for example, Patent Document 1).

[0004] In the heat dissipation materials described above, silicone resin, polyolefin resin, acrylic resin, or epoxy resin are typically used as the resin binder.

[0005] Heat dissipation materials are generally required to have excellent thermal conductivity, and additional functions may be required depending on the application. For example, depending on the application, the heat dissipation material may be required to exhibit low adhesive strength to a specific substrate in addition to high thermal conductivity.

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

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

[0008] The polyurethane material used in Patent Document 1 can form a heat dissipation material with high thermal conductivity and has various other advantages, but it is also a material that exhibits high adhesive strength to most adherends.

[0009] One method to reduce the adhesive strength of materials exhibiting high adhesive strength is to incorporate known components as plasticizers. However, plasticizers added in large quantities to control adhesive strength can impair the inherent advantages of the material itself or leach out during use, leading to problems. [Prior art documents] [Patent Documents]

[0010] [Patent Document 1] Korean Published Patent Gazette No. 2016-0105354 [Overview of the Initiative] [Problems that the invention aims to solve]

[0011] This application aims to provide a curable composition. One objective of this application is to enable the curable composition or its cured product to exhibit high thermal conductivity and low adhesive strength to a predetermined adherend. Another objective of this application is to achieve the low adhesive strength without using adhesive strength modifying components such as plasticizers, or by minimizing their usage.

[0012] One objective of this application is to provide a product comprising the curable composition or its cured form. [Means for solving the problem]

[0013] Where the measurement temperature affects the results of any physical properties mentioned herein, unless otherwise specified, those properties are those measured at room temperature. The term "room temperature" refers to the natural temperature, without heating or deheating, and typically means a single temperature within the range of approximately 10°C to 30°C, or a temperature of approximately 23°C or 25°C. Unless otherwise specified herein, the unit of temperature is °C.

[0014] When the measured pressure affects the result among the physical properties mentioned in this specification, unless otherwise specified, the physical property is the physical property measured at normal pressure. The term "normal pressure" refers to the natural pressure without pressurization or depressurization, and usually, a pressure of about 700 mmHg to 800 mmHg is called normal pressure.

[0015] This application relates to a resin composition. The term "resin composition" means a composition containing components known as resins in the industry or a composition that does not contain resins but contains components that can form resins through a curing reaction or the like.

[0016] Therefore, in the scope of the term "resin" or "resin component" in this specification, it includes not only components generally known as resins but also components that can form resins through a curing and / or polymerization reaction.

[0017] The resin composition may be a curable composition.

[0018] When the resin composition of this application is a curable composition, the resin composition may be a one-component type or a two-component type resin composition. The term "one-component type resin composition" means a resin composition in which the components participating in curing are contained in a state of being physically in contact with each other, and the term "two-component type resin composition" means a resin composition in which at least a part of the components participating in curing are physically separated and contained.

[0019] When the resin composition of this application is a curable composition, the resin composition may be a room temperature curing type, a heat curing type, an energy ray curing type and / or a moisture curing type. The term "room temperature curing type" refers to a resin composition in which the curing reaction can start and / or proceed at room temperature, the term "heat curing type" refers to a resin composition in which the curing reaction can start and / or proceed by the application of heat, the term "energy ray curing type" refers to a resin composition in which the curing reaction can start and / or proceed by the irradiation of energy rays (for example, ultraviolet rays, electron beams, etc.), and the term "moisture curing type" refers to a resin composition in which the curing reaction can start and / or proceed in the presence of moisture.

[0020] The resin composition of the present application may be a solvent type or a solventless type. Considering aspects such as application efficiency and environmental load, it is appropriate to be a solventless type.

[0021] The resin composition of the present application may be a polyurethane composition. In such a case, the resin composition may contain polyurethane or components capable of forming polyurethane.

[0022] The resin composition of the present application may exhibit low adhesive force to a specific adherend or form a cured body capable of exhibiting low adhesive force. Such a resin composition of the present application may be a polyurethane composition. Polyurethane is known as an adhesive material capable of exhibiting excellent adhesion to various adherends. Therefore, as a method for making the polyurethane composition exhibit low adhesive force to the adherend, usually, a method of introducing a component for reducing adhesive force such as a plasticizer is used. When such a component such as a plasticizer is applied, the adhesive force of the polyurethane material can be reduced, but problems may occur such as reducing other physical properties that the component can secure from the polyurethane or eluting the component outside the material during the use process of the polyurethane material. However, in the present application, a component for reducing adhesive force such as a plasticizer is not used or its usage amount is minimized, and the low adhesive force can be achieved with respect to the polyurethane material. Therefore, the present application can provide a material that has the advantages of the polyurethane material and solves the problem of high adhesive force that is not required according to the application.

[0023] The resin composition or its cured body can exhibit controlled adhesive force to aluminum. For example, the upper limit of the adhesive force to the aluminum is 1 N / mm 2 , 0.9 N / mm 2 , 0.8 N / mm 2 , 0.7 N / mm 2 , 0.6 N / mm 2 , 0.5 N / mm 2 , 0.4 N / mm 2 , 0.3 N / mm 2 , 0.2 N / mm 2, 0.1 N / mm 2 , 0.09 N / mm 2 , 0.08 N / mm 2 , 0.07 N / mm 2 , 0.06 N / mm 2 , 0.04 N / mm 2 or 0.03 N / mm 2 This may also be the case. The lower limit of the adhesive strength to aluminum is not particularly limited. In one example, the lower limit of the adhesive strength to aluminum is 0 N / mm 2 , 0.0001 N / mm 2 , 0.0005 N / mm 2 , 0.001 N / mm 2 , 0.005 N / mm 2 , 0.01 N / mm 2 , 0.015 N / mm 2 , 0.02 N / mm 2 , 0.025 N / mm 2 or 0.03 N / mm 2 It may be to a certain extent. That is, the resin composition may be a resin composition in which the adhesive strength to aluminum is substantially not measurable, or a resin composition that can form a cured product in which the adhesive strength to aluminum is substantially not measurable. The adhesive strength to aluminum may be less than or equal to any of the upper limits mentioned above, or greater than or equal to the lower limit mentioned above or greater than the lower limit mentioned above, or greater than or equal to the lower limit mentioned above or greater than the lower limit, while being less than or equal to any of the upper limits mentioned above. The adhesive strength to aluminum may be measured by the method described in the examples of this specification.

[0024] The resin composition or its cured form can exhibit controlled adhesion to polyester. For example, the upper limits of the adhesion to polyester are 2,000 gf / 10 mm, 1,800 gf / 10 mm, 1,600 gf / 10 mm, 1,400 gf / 10 mm, 1,200 gf / 10 mm, 1,000 gf / 10 mm, 950 gf / 10 mm, 850 gf / 10 mm, 800 gf / 10 mm, 750 gf / 10 mm, 700 gf / 10 mm, 650 gf / 10 mm, 600 gf / 10 mm, 550 gf / 10 mm, and 500 g. The adhesive strength may be f / 10mm, 450gf / 10mm, 400gf / 10mm, 350gf / 10mm, 300gf / 10mm, 250gf / 10mm, 200gf / 10mm, 150gf / 10mm, 100gf / 10mm, 90gf / 10mm, 80gf / 10mm, 70gf / 10mm, 60gf / 10mm, 50gf / 10mm, 40gf / 10mm, 30gf / 10mm, 20gf / 10mm, or 10gf / 10mm. In this application, the lower limit of the adhesive strength to polyester is not particularly limited. In one example, the lower limit of the adhesive strength to polyester may be 0gf / 10mm. That is, the resin composition or its cured product may not substantially exhibit adhesive strength to polyester. Therefore, the adhesive strength of the resin composition or its cured form to polyester may be 0 gf / 10 mm or more. For example, the lower limit of the adhesive strength to polyester may be 0 gf / 10 mm, 5 gf / 10 mm, 10 gf / 10 mm, 15 gf / 10 mm, 20 gf / 10 mm, 25 gf / 10 mm, 30 gf / 10 mm, 35 gf / 10 mm, 40 gf / 10 mm, 45 gf / 10 mm, 50 gf / 10 mm, 55 gf / 10 mm, 60 gf / 10 mm, 65 gf / 10 mm, 70 gf / 10 mm, 75 gf / 10 mm, 80 gf / 10 mm, 85 gf / 10 mm, 90 gf / 10 mm, or 95 gf / 10 mm.The adhesive strength to the polyester may be less than or equal to any of the upper limits mentioned above, greater than or equal to any of the lower limits mentioned above, or greater than or equal to any of the lower limits mentioned above, while remaining within the range of less than or equal to any of the upper limits mentioned above. The adhesive strength to the polyester may be measured by the method described in the examples of this specification.

[0025] The resin composition or its cured form can exhibit the aforementioned adhesive strength to a specific adherend (e.g., aluminum and / or polyester) and also exhibit excellent thermal conductivity. For example, the lower limit of the thermal conductivity of the resin composition or its cured form may be around 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, 2.6 W / mK, or 2.8 W / mK. The upper limit of the thermal conductivity is not particularly limited. For example, the upper limit of the thermal conductivity of the resin composition or its cured form may be around 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 less than or equal to any of the upper limits mentioned above, greater than or equal to any of the lower limits mentioned above, or greater than or equal to any of the lower limits mentioned above while remaining within the range of less than or equal to any of the upper limits mentioned above. The thermal conductivity of such a resin composition or its cured product can be measured by the method disclosed in the examples described later.

[0026] The aforementioned resin composition or its cured product can exhibit appropriate hardness. For example, if the hardness of the resin composition or its cured product is too high, excessive brittleness may occur, causing problems. Furthermore, by adjusting the hardness of the resin composition or its cured product, impact resistance and vibration resistance can be ensured according to the application, thereby ensuring the durability of the product.

[0027] For example, the upper limit of the Shore OO hardness of the resin composition or its cured product may be 150, 140, 130, 120, 110, 100, 95, 90, 80, 70, 60, 50, or 45, and the lower limit may be approximately 0, 5, 10, 15, 20, 25, 30, 35, 40, 45, 50, 55, 60, 65, 70, 75, 80, or 85. The Shore OO hardness may be less than or equal to any of the upper limits mentioned above, greater than or equal to any of the lower limits mentioned above, or greater than or equal to any of the lower limits mentioned above while remaining within the range of less than or equal to any of the upper limits mentioned above. The hardness of such a resin composition or its cured product can be measured by the method disclosed in the examples described later.

[0028] The resin composition or its cured product may exhibit even more appropriate flexibility. For example, by adjusting the flexibility of the resin composition or its cured product to a desired level, the range of applications can be greatly expanded. For example, the lower limit of the radius of curvature of the resin composition or its cured product may be around 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, or 12, and the upper limit may be around 20, 19, 18, 17, 16, 15, 14, 13, 12, 11, 10, 9, 8, 7, 6, 5, or 4. The radius of curvature may be less than or equal to any of the upper limits mentioned above, greater than or equal to any of the lower limits mentioned above, or greater than or equal to any of the lower limits mentioned above, while being within the range of less than or equal to any of the upper limits mentioned above. The radius of curvature of such a resin composition or its cured product may be measured by the method disclosed in the examples described later. Unless otherwise specified, the unit of radius of curvature in this specification is mm.

[0029] The resin composition of this application may be insulating. That is, the resin composition may be insulating and / or form an insulating cured body. For example, the resin composition or its cured body may have a dielectric breakdown voltage of about 3kV / mm or more, about 5kV / mm or more, about 7kV / mm or more, 10kV / mm or more, 15kV / mm or more, or 20kV / mm or more, as measured in accordance with ASTM D149. The higher the dielectric breakdown voltage, the better the insulating properties. There is no particular upper limit, but considering the composition of the resin composition, the dielectric breakdown voltage may be about 50kV / mm or less, 45kV / mm or less, 40kV / mm or less, 35kV / mm or less, or 30kV / mm or less. Such dielectric breakdown voltages can be controlled by adjusting the insulating properties of the resin composition, for example, by applying an insulating filler in the resin layer. Ceramic fillers are generally known as components that can ensure insulating properties.

[0030] The resin composition or its cured product may be flame-retardant. For example, the resin composition or its cured product may exhibit a V-0 rating in the UL 94 V Test (Vertical Burning Test). This ensures stability against fire and other accidents that may be a concern depending on the application of the resin composition.

[0031] The resin composition or its cured product may have a specific gravity of 5 or less. In other examples, the specific gravity may be 4.5 or less, 4 or less, 3.5 or less, or 3 or less. Resin layers exhibiting a specific gravity in such a range are advantageous for providing lighter products. The lower limit of the specific gravity is not particularly limited. For example, the specific gravity may be about 1.5 or more, or 2 or more. The components added to the resin layer in order for the resin composition or its cured product to exhibit the specified gravity may be adjusted. For example, a filler that ensures the desired properties (e.g., thermal conductivity) even at the lowest possible specific gravity when the filler is added may be used, i.e., a filler with a low specific gravity on its own may be used, or a surface-treated filler may be used.

[0032] The resin composition may have a low shrinkage rate during or after the curing process. This prevents peeling and void formation that may occur during the application process. The shrinkage rate may be adjusted as appropriate within a range that exhibits the effects described above, for example, it may be less than 5%, less than 3%, or less than approximately 1%. Since a lower shrinkage rate is more advantageous, there is no particular lower limit.

[0033] The resin composition or its cured product may have a low coefficient of thermal expansion (CTE). This prevents peeling and void formation that may occur during application or use. The coefficient of thermal expansion may be adjusted as appropriate within a range that exhibits the effects described above, 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 approximately 100 ppm / K. Since a lower value for the coefficient of thermal expansion is advantageous, there is no particular limit to its lower limit.

[0034] The resin composition or its cured product may further have a 5% weight loss temperature of 400°C or higher in thermogravimetric analysis (TGA), or an 800°C residue of 70% by weight or more. Such properties can further improve stability at high temperatures. The 800°C residue may, in other examples, be about 75% by weight or more, about 80% by weight or more, about 85% by weight or more, or about 90% by weight or more. The 800°C residue may, in other examples, be about 99% by weight or less. The thermogravimetric analysis (TGA) is performed at 60 cm³. 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 residue is usually dependent on the type or proportion of fillers contained in the resin composition, and the residue increases if an excessive amount of filler is included.

[0035] The resin composition of this application may contain a hydroxyl-functionalized component. The term "hydroxyl-functionalized component" refers to all compounds having a hydroxyl group that are present in the resin composition. Therefore, if there is one compound having a hydroxyl group in the resin composition, that compound becomes the hydroxyl-functionalized component, and if there are two or more compounds having a hydroxyl group in the resin composition, a mixture of those two or more compounds becomes the hydroxyl-functionalized component.

[0036] Examples of compounds having hydroxyl groups that form the aforementioned hydroxyl functional components include, but are not limited to, oil-modified polyol compounds, general polyol compounds, and oil-modified alcohol compounds.

[0037] The hydroxyl-functional component may include a polyol compound. The term "polyol compound" refers to a compound containing two or more hydroxyl groups. Such polyol compounds are sometimes called polyfunctional polyol compounds. Such polyol compounds may be monomolecular, oligomeric, or polymeric compounds. The lower limit of the number of hydroxyl groups contained in the polyol compound may be around two or three, and the upper limit may be around 10, 9, 8, 7, 6, 5, 4, 3, or 2. The number of hydroxyl groups in the polyol compound may be less than or equal to any of the upper limits mentioned above, or greater than or equal to any of the lower limits mentioned above, while being greater than or equal to any of the upper limits mentioned above.

[0038] The number of hydroxyl groups contained in a polyol compound is usually, 1 This can be confirmed by 1H NMR, 1 The number of hydroxyl groups can be determined based on the peaks present in the 3-4 ppm region in the 1H NMR spectrum.

[0039] The polyol compounds of this application may also be oil-modified polyol compounds. The term "oil-modified polyol compound" means a compound containing at least two hydroxyl groups and at least one oil group at its terminus. The oil group may be a linear or branched hydrocarbon group with three or more carbon atoms. Whether a polyol compound contains the hydrocarbon group that is the oil group is usually determined by... 1 This can be confirmed by 1H NMR, 1 The presence and number of hydrocarbon groups can be confirmed based on peaks in the 4-5 ppm range observed in 1H NMR. Such polyol compounds may be monomolecular, oligomeric, or polymeric compounds. By applying such oil-modified polyol compounds, it is possible to form polyurethane materials while ensuring low adhesion to specific materials without using plasticizers or other adhesive-reducing components, or by minimizing their use.

[0040] The lower limit of the number of linear or branched hydrocarbon groups that constitute the oil group may be 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, or 17, and the upper limit may be approximately 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, or 10. The number of carbon atoms may be less than or equal to any of the upper limits mentioned above, greater than or equal to any of the lower limits mentioned above, or greater than or equal to any of the lower limits mentioned above, while remaining within the range of less than or equal to any of the upper limits mentioned above.

[0041] The oil group, which is a straight-chain or branched-chain hydrocarbon group, may or may not contain a double bond. If it contains a double bond, this double bond may be a conjugated double bond or a cis double bond.

[0042] Specific types of hydrocarbon groups that constitute the oil group include alkyl groups, alkenyl groups, or alkynyl groups. In one example, the hydrocarbon group may be linked to the polyol compound via a carbonyl group or carbonyloxy group, in which case the hydrocarbon group that constitutes the oil 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 lower limit of the number of carbon atoms in the alkyl group, alkenyl group, or alkynyl group may be around 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, or 17, and the upper limit may be 50, 49, 48, 47, 46, 45, 44, or 43. The number of carbon atoms may be approximately 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, or 10. The number of carbon atoms may be less than or equal to any of the upper limits mentioned above, greater than or equal to any of the lower limits mentioned above, or greater than or equal to any of the lower limits mentioned above, while remaining within the range of less than or equal to any of the upper limits mentioned above.

[0043] The alkyl group, alkenyl group, or alkynyl group may be linear or branched, and may be optionally substituted with one or more substituents. If substituents are present, there are no particular restrictions on the type of substituent; for example, halogen atoms such as fluorine can be used as substituents.

[0044] In one example, the hydrocarbon group may be included in the substituent in the following chemical formula 1.

[0045] [ka]

[0046] In Chemical Formula 1, R is the hydrocarbon group having three or more carbon atoms and being either a straight chain or a branched chain. In Chemical Formula 1, the asterisk (*) indicates that the portion is linked to the polyol compound. Therefore, an oxygen atom may be linked to the polyol compound in the substituent in Chemical Formula 1.

[0047] The specific type of hydrocarbon group R in Chemical Formula 1 is as described above. Therefore, the details regarding the number, type, form, and substituents of carbon atoms in the hydrocarbon group described above may be applied in the same manner as described above.

[0048] The number of hydrocarbon groups contained in the polyol compound is not particularly limited, but in one example, the polyol compound may contain one or more or two or more hydrocarbon groups per molecule. There is no particular upper limit on the number of hydrocarbon groups contained in the polyol compound, but for example, the number of hydrocarbon groups per molecule of the polyol compound may be approximately 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.

[0049] The polyol compound may take various forms, as long as it contains the aforementioned hydroxyl group and hydrocarbon group.

[0050] In one example, the polyol compound may be a compound in which at least some of the hydrogen atoms of a hydrocarbon compound such as an alkane, alkene, or alkyne are substituted with hydroxyl groups and / or hydrocarbon groups. The number of carbon atoms in the hydrocarbon compound such as the alkane, alkene, or alkyne may be, for example, 1 to 20, 1 to 16, 1 to 8, or 4 to 6.

[0051] Such hydrocarbon compounds, such as alkanes, alkenes, or alkynes, may be linear, branched, or cyclic. Furthermore, the hydroxyl group and / or hydrocarbon group may be substituted on the same carbon atom in the alkane, alkene, or alkyne, or on other carbon atoms.

[0052] In other examples, the polyol compound may be a compound having a polyester skeleton or a polyether skeleton. In such cases, the polyol compound may be an oligomeric compound or a polymeric compound.

[0053] In one example, the polyol compound having a polyester skeleton is a so-called polyester polyol, and may also be a polyol having a structure in which the hydrocarbon group is linked to such a polyester polyol.

[0054] Furthermore, the polyol compound having the polyether skeleton is a so-called polyether polyol, and may also be a polyol having a structure in which the hydrocarbon group is linked to such a polyether polyol.

[0055] In one example, the polyester skeleton may be a so-called polycaprolactone skeleton, and the polyether skeleton may be a so-called polyalkylene skeleton.

[0056] In one example, the polyester skeleton may be a skeleton having repeating units represented by the following chemical formula 2.

[0057] [ka]

[0058] In chemical formula 2, X1 and X2 are independently single bonds or oxygen atoms, L1 may be an alkylene group, and n is any number.

[0059] In this specification, the term "single bond" means a situation where no atom is present at the site in question.

[0060] In chemical formula 2, the alkylene group may, in one example, be an alkylene 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.

[0061] In this specification, the term alkylene group means a divalent substituent formed by the removal of two hydrogen atoms from an alkane, where the two hydrogen atoms may be removed one from each of the other carbon atoms of the alkane, or the alkane may be removed from one carbon atom.

[0062] As will be described later, in one example, the polyester skeleton may be a polycaprolactone skeleton, in which case, in the above formula 2, L1 may be a linear alkylene group having 5 carbon atoms.

[0063] In equation 2, n is any number representing the number of repeating units, and may be, for example, a number within the range of 1 to 25.

[0064] In formula 2, the lower limit of n may be approximately 1, 3, 5, 7, 9, 11, 13, 15, 17, 19, 21, or 23, and the upper limit may be approximately 25, 23, 21, 19, 17, 15, 13, 11, 9, 7, 5, or 3. The aforementioned n may be less than or equal to any of the upper limits mentioned above, greater than or equal to any of the lower limits mentioned above, or greater than or equal to any of the lower limits mentioned above, while being within the range of less than or equal to any of the upper limits mentioned above.

[0065] The skeleton of chemical formula 2 is a polyester polyol skeleton, and may be a so-called carboxylic acid polyol skeleton or a caprolactone polyol skeleton. Such skeletons may be formed by known methods; for example, the carboxylic acid polyol skeleton may be formed by reacting a carboxylic acid with a component containing a polyol (e.g., a diol or triol), and the caprolactone polyol skeleton may be formed by reacting caprolactone with a component containing a polyol (e.g., a diol or triol). The carboxylic acid may be a dicarboxylic acid.

[0066] In a polyol compound having the skeleton of Chemical Formula 2, the hydroxyl group or the aforementioned hydrocarbon group may be located at the terminal end of the skeleton of Chemical Formula 2.

[0067] In such a case, the framework of formula 2 is represented by formula 3 below.

[0068] [ka]

[0069] In chemical formula 3, X1, X2, L1, and n are as defined in chemical formula 2, and R1 may be a hydroxyl group or a substituent as shown in chemical formula 4 below.

[0070] [ka]

[0071] In chemical formula 4, X3 is a single bond or an oxygen atom, and R is the same as R in chemical formula 1.

[0072] In chemical formula 3, if R1 is a hydroxyl group, X1 is a single bond; if R1 is the substituent in chemical formula 4, then either X1 or X3 is a single bond and the other is an oxygen atom.

[0073] The lower limit of the number of skeletons of formula 2 or 3 contained in the polyol compound may be about 1 or 2, and the upper limit may be about 10, 9, 8, 7, 6, 5, 4, 3, or 2. The number of skeletons may be less than or equal to any of the upper limits mentioned above, greater than or equal to any of the lower limits mentioned above, or greater than or equal to any of the lower limits mentioned above, while remaining within the range of less than or equal to any of the upper limits mentioned above.

[0074] The polyol compound having the polyester skeleton may have a linear or branched structure.

[0075] In the above, the linear structure is a structure in which a main chain containing the skeleton of formula 2 or 3 exists, and no other polymer chains are linked to the main chain, and the branched chain structure may be a form in which chains containing the skeleton of formula 2 or 3 are linked as side chains to the main chain containing the skeleton of formula 2 or 3. The number of chains containing the skeleton of 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.

[0076] In one example, the polyol compound having a polyester skeleton may be a compound in which at least some of the hydrogen atoms of a hydrocarbon compound such as an alkane, alkene, or alkyne are substituted with the hydroxyl group and / or the skeleton of 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.

[0077] Such hydrocarbon compounds, such as alkanes, alkenes, or alkynes, may be linear, branched, or cyclic. Furthermore, the hydroxyl group and / or the skeleton of formula 3 may be substituted with the same carbon atom in the alkane, alkene, or alkyne, or with other carbon atoms.

[0078] In one example, the polyether skeleton may be a skeleton having repeating units represented by the following chemical formula 5.

[0079] [ka]

[0080] In chemical formula 5, X4 and X5 are independently single bonds or oxygen atoms, L2 is an alkylene group, and m is any number.

[0081] In the above formula 5, the alkylene group may, in one example, be an alkylene group having 1 to 20 carbon atoms, 1 to 16 carbon atoms, 1 to 12 carbon atoms, 1 to 8 carbon atoms, or 1 to 4 carbon atoms, and may be linear or branched in shape.

[0082] In formula 5 above, m is any number representing the number of repeating units, and may be, for example, a number within the range of 1 to 25.

[0083] In formula 5, the lower limit of m may be approximately 1, 3, 5, 7, 9, 11, 13, 15, 17, 19, 21, or 23, and the upper limit may be approximately 25, 23, 21, 19, 17, 15, 13, 11, 9, 7, 5, or 3. The aforementioned m may be less than or equal to any of the upper limits mentioned above, greater than or equal to any of the lower limits mentioned above, or greater than or equal to any of the lower limits mentioned above, while remaining within the range of less than or equal to any of the upper limits mentioned above.

[0084] In a polyol compound having the skeleton of chemical formula 5, the hydroxyl group or the aforementioned hydrocarbon group may be located at the terminal end of the skeleton of chemical formula 5.

[0085] In such a case, the framework of formula 5 is represented by formula 6 below.

[0086] [ka]

[0087] In chemical formula 6, X4, X5, L2, and m are as defined in chemical formula 5, and R2 may be a hydroxyl group or a substituent as shown in chemical formula 7 below.

[0088] [ka]

[0089] In chemical formula 7, X6 is a single bond or an oxygen atom, and R is the same as R in chemical formula 1.

[0090] In chemical formula 6, if R2 is a hydroxyl group, X4 is a single bond; if R2 is the substituent in chemical formula 7, then either X4 or X6 is a single bond and the other is an oxygen atom.

[0091] The lower limit of the number of skeletons of formula 5 or 6 contained in the polyol compound may be about 1 or 2, and the upper limit may be about 10, 9, 8, 7, 6, 5, 4, 3, or 2. The number of skeletons may be less than or equal to any of the upper limits mentioned above, greater than or equal to any of the lower limits mentioned above, or greater than or equal to any of the lower limits mentioned above, while remaining within the range of less than or equal to any of the upper limits mentioned above.

[0092] The polyol compound having the polyether skeleton may have a linear or branched chain structure.

[0093] In the above, the linear structure is a structure in which a main chain containing the skeleton of formula 5 or 6 exists, and no other polymer chains are linked to the main chain, and the branched chain structure may be a form in which chains containing the skeleton of formula 5 or 6 are linked as side chains to the main chain containing the skeleton of formula 5 or 6. The number of chains containing the skeleton of 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.

[0094] In one example, the polyol compound having the polyether skeleton may be a compound in which at least some of the hydrogen atoms of a hydrocarbon compound such as an alkane, alkene, or alkyne are substituted with a hydroxyl group and / or the skeleton of 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.

[0095] Such hydrocarbon compounds, such as alkanes, alkenes, or alkynes, may be linear, branched, or cyclic. Furthermore, the hydroxyl group and / or the skeleton of formula 5 may be substituted with the same carbon atom in the alkane, alkene, or alkyne, or with other carbon atoms.

[0096] If the polyol compound described above is an oligomeric or polymeric compound, it may have an appropriate molecular weight.

[0097] For example, the lower limit of the weight-average molecular weight of the oligomeric or polymeric polyol compound may be around 100 g / mol, 200 g / mol, 300 g / mol, 400 g / mol, 500 g / mol, 600 g / mol, 700 g / mol, 800 g / mol, or 900 g / mol, and the upper limit may be around 5000 g / mol, 4500 g / mol, 4000 g / mol, 3500 g / mol, 3000 g / mol, 2500 g / mol, 2000 g / mol, 1500 g / mol, 1000 g / mol, or 800 g / mol. The weight-average molecular weight may be less than or equal to any of the upper limits mentioned above, greater than or equal to any of the lower limits mentioned above, or greater than or equal to any of the lower limits mentioned above, while being within the range of less than or equal to any of the upper limits mentioned above.

[0098] By applying the oil-modified polyol compounds described above, the desired physical properties can be more effectively ensured.

[0099] The oil-modified polyol compound may be present in the resin composition in an appropriate proportion. For example, the lower limit of the content of the oil-modified polyol compound in the resin composition may be approximately 5% by weight, 10% by weight, 15% by weight, 20% by weight, 25% by weight, 30% by weight, 35% by weight, 40% by weight, 45% by weight, 50% by weight, 55% by weight, 60% by weight, 65% by weight, 70% by weight, 75% by weight, 80% by weight, 85% by weight, 90% by weight, or 95% by weight, and the upper limit may be approximately 100% by weight, 95% by weight, 90% by weight, 85% by weight, 80% by weight, 75% by weight, 70% by weight, 65% by weight, 60% by weight, 55% by weight, 50% by weight, 45% by weight, 40% by weight, 35% by weight, 30% by weight, 25% by weight, or 20% by weight. The content may be less than or equal to any of the upper limits mentioned above, greater than or equal to any of the lower limits mentioned above, or greater than or equal to any of the lower limits mentioned above, while remaining within the range of less than or equal to any of the upper limits mentioned above.

[0100] The content of the oil-modified polyol compound is, in the case of a one-component resin composition, the content within the one-component resin composition, and in the case of a two-component composition, the content within the part in which the oil-modified polyol compound is present. For example, if a two-component resin composition includes a physically separated main component part and a curing agent part, and the oil-modified polyol compound is included in the main component part, the content of the oil-modified polyol may be the content based on the total weight of the main component part. Furthermore, if the resin composition contains a solvent and / or filler, the content is the content based on the weight excluding the content of the solvent and filler.

[0101] In other examples, if the resin composition contains a filler component described later, the lower limit of the content of the oil-modified polyol compound relative to 100 parts by weight of the filler component may be about 1, 3, 5, 7, 9, 11, or 13 parts by weight, and the upper limit may be about 40, 35, 30, 25, 20, 15, 10, 8, 6, 4, or 3 parts by weight. The content may be less than or equal to any of the upper limits mentioned above, greater than or equal to any of the lower limits mentioned above, or greater than or equal to any of the lower limits mentioned above, while remaining within the range of less than or equal to any of the upper limits mentioned above.

[0102] The ratio to the filler component is the ratio to 100 parts by weight of the total filler component contained in the resin composition when the resin composition is a one-component type, and the ratio to 100 parts by weight of the total filler component present in the part containing the oil-modified polyol (main component part or curing agent part) when the resin composition is a two-component type.

[0103] The hydroxyl functional component may optionally further contain an alcohol compound. In this terminology, an alcohol compound means a compound containing one hydroxyl group per molecule. Such an alcohol compound may be monomolecular, oligomeric, or polymeric.

[0104] When an alcohol compound is used, an oil-modified alcohol compound may be used instead of the alcohol compound. The term "oil-modified alcohol compound" refers to a compound containing one hydroxyl group per molecule and at least one linear or branched hydrocarbon group with three or more carbon atoms at its terminus, which is the oil group. The method for confirming the number of hydroxyl groups and hydrocarbon groups is the same as for the polyol compound. Such an alcohol compound may be monomolecular, oligomeric, or polymeric. By applying such an oil-modified alcohol compound together with the aforementioned oil-modified polyol compound, it is possible to form a material from a polyurethane material while ensuring low adhesion to specific materials without using or minimizing the use of adhesive-reducing components such as plasticizers.

[0105] The oil-modified alcohol compound may have a form similar to the oil-modified polyol compound, except that it contains one hydroxyl group per molecule. Therefore, the description of the oil-modified polyol compound may also apply to the oil-modified alcohol compound, except for the number of hydroxyl groups.

[0106] Therefore, for example, the lower limit of the number of carbon atoms in the straight-chain or branched-chain hydrocarbon group present in the oil-modified alcohol compound may be around 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, or 17, and the upper limit may be 50, 49, 48, 47, 46, 45, or 4 The number of carbon atoms may be approximately 4, 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, or 10. The number of carbon atoms may be less than or equal to any of the upper limits mentioned above, greater than or equal to any of the lower limits mentioned above, or greater than or equal to any of the lower limits mentioned above, while remaining within the range of less than or equal to any of the upper limits mentioned above.

[0107] The aforementioned linear or branched hydrocarbon group may or may not contain a double bond. If it contains a double bond, this double bond may be a conjugated double bond or a cis double bond.

[0108] Specific types of hydrocarbon groups include alkyl groups, alkenyl groups, or alkynyl groups. In one example, the hydrocarbon group may be linked to the alcohol compound via a carbonyl group or 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. The lower limit of the number of carbon atoms in the alkyl, alkenyl, or alkynyl group may be approximately 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, or 17, and the upper limit may be approximately 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, or 10. The number of carbon atoms may be less than or equal to any of the upper limits mentioned above, greater than or equal to any of the lower limits mentioned above, or greater than or equal to any of the lower limits mentioned above, while remaining within the range of less than or equal to any of the upper limits mentioned above.

[0109] The alkyl group, alkenyl group, or alkynyl group may be linear or branched, and may be optionally substituted with one or more substituents. If substituents are present, there are no particular restrictions on the type of substituent; for example, halogen atoms such as fluorine can be used as substituents.

[0110] In one example, the hydrocarbon group of the oil-modified alcohol compound may also be included in the substituents of Formula 1 described above. In this case, the details regarding the substituents of Formula 1 are the same as in the case of the oil-modified polyol compound.

[0111] The number of hydrocarbon groups contained in the alcohol compound is not particularly limited, but in one example, the lower limit of the number of hydrocarbon groups contained in the alcohol compound may be about 1 or 2 per molecule, and the upper limit may be about 10, 9, 8, 7, 6, 5, 4, 3, or 2 per molecule. The number of carbon atoms may be less than or equal to any of the upper limits mentioned above, or greater than or equal to any of the lower limits mentioned above, or greater than or equal to any of the lower limits mentioned above, while being within the range of less than or equal to any of the upper limits mentioned above.

[0112] The alcohol compound may take various forms, as long as it contains the aforementioned hydroxyl group and hydrocarbon group.

[0113] In one example, the alcohol compound may be a compound in which at least some of the hydrogen atoms of a hydrocarbon compound such as an alkane, alkene, or alkyne are substituted with one hydroxyl group and / or the hydrocarbon group. The number of carbon atoms in the hydrocarbon compound such as the alkane, alkene, or alkyne may be, for example, 1 to 20, 1 to 16, 1 to 8, or 4 to 6.

[0114] Such hydrocarbon compounds, such as alkanes, alkenes, or alkynes, may be linear, branched, or cyclic. Furthermore, the hydroxyl group and / or hydrocarbon group may be substituted on the same carbon atom in the alkane, alkene, or alkyne, or on other carbon atoms.

[0115] In other examples, the alcohol compound may be a compound having a polyester or polyether skeleton. In such cases, the alcohol compound may be an oligomeric compound or a polymeric compound.

[0116] Similar to the case of polyol compounds, the polyester skeleton may be a so-called polycaprolactone skeleton, and the polyether skeleton may be a so-called polyalkylene skeleton.

[0117] In one example, the polyester skeleton may be a skeleton having repeating units represented by chemical formula 2. In this case, the specific details of the repeating units in chemical formula 2 are the same as in the case of the polyol compound.

[0118] Therefore, even in the case of oil-modified alcohol compounds, the hydroxyl group or the aforementioned hydrocarbon group in the alcohol compound having the skeleton of Formula 2 may be located at the end of the skeleton of Formula 2, and in such cases the skeleton of Formula 2 is represented by Formula 3. At this time, the specific details of the skeleton of Formula 3 are the same as in the case of the polyol compound.

[0119] The lower limit of the number of skeletons in the alcohol compound described in formula 2 or 3 may be about one or two, assuming that the compound contains one hydroxyl group per molecule, and the upper limit may be about 10, 9, 8, 7, 6, 5, 4, 3, or 2. The number of skeletons may be less than or equal to any of the upper limits mentioned above, greater than or equal to any of the lower limits mentioned above, or greater than or equal to any of the lower limits mentioned above, while remaining within the range of less than or equal to any of the upper limits mentioned above.

[0120] The alcohol compound having the polyester skeleton may also have a linear or branched structure.

[0121] The linear structure is a structure in which a main chain containing the skeleton of formula 2 or 3 exists, and no other polymer chains are linked to the main chain. The branched chain structure may be a form in which chains containing the skeleton of formula 2 or 3 are linked as side chains to the main chain containing the skeleton of formula 2 or 3. The number of chains containing the skeleton of 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.

[0122] In one example, the alcohol compound having the polyester skeleton may also be a compound in which at least some of the hydrogen atoms of a hydrocarbon compound such as an alkane, alkene, or alkyne are substituted with the hydroxyl group and / or the skeleton of formula 3. The number of carbon atoms in the hydrocarbon compound such as the alkane, alkene, or alkyne may be, for example, 1 to 20, 1 to 16, 1 to 8, or 4 to 6.

[0123] Such hydrocarbon compounds, such as alkanes, alkenes, or alkynes, may be linear, branched, or cyclic. Furthermore, the hydroxyl group and / or the skeleton of formula 3 may be substituted with the same carbon atom in the alkane, alkene, or alkyne, or with other carbon atoms.

[0124] The polyether skeleton of the alcohol compound may, in one example, be a skeleton having repeating units represented by the formula 5. In this case, the specific details of formula 5 are the same as in the case of the polyol compound.

[0125] In alcohol compounds having the skeleton of Formula 5, the hydroxyl group or the aforementioned hydrocarbon group may be located at the end of the skeleton of Formula 5, and this may be the skeleton represented by Formula 6. In this case, the specific details of Formula 6 are the same as in the case of the polyol compound.

[0126] Assuming that the alcohol compound has one hydroxyl group per molecule, the lower limit of the number of skeletons of formula 5 or 6 contained in the alcohol compound may be about one or two, and the upper limit may be about 10, 9, 8, 7, 6, 5, 4, 3, or 2. The number of skeletons may be less than or equal to any of the upper limits mentioned above, greater than or equal to any of the lower limits mentioned above, or greater than or equal to any of the lower limits mentioned above, while remaining within the range of less than or equal to any of the upper limits mentioned above.

[0127] The alcohol compound having the polyether skeleton may also have a linear or branched structure.

[0128] The linear structure is a structure in which a main chain containing the skeleton of formula 5 or 6 exists, and no other polymer chains are linked to the main chain. The branched structure may be a form in which chains containing the skeleton of formula 5 or 6 are linked as side chains to the main chain containing the skeleton of formula 5 or 6. The number of chains containing the skeleton of formula 5 or 6 linked as side chains in the branched structure may be, for example, 1 to 5, 1 to 4, 1 to 3, 1 to 2, or 1.

[0129] In one example, the alcohol compound having a polyether skeleton may be a compound in which at least some of the hydrogen atoms of a hydrocarbon compound such as an alkane, alkene, or alkyne are substituted with a hydroxyl group and / or the skeleton of 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.

[0130] Such hydrocarbon compounds, such as alkanes, alkenes, or alkynes, may be linear, branched, or cyclic. Furthermore, the hydroxyl group and / or the skeleton of formula 5 may be substituted with the same carbon atom in the alkane, alkene, or alkyne, or with other carbon atoms.

[0131] If the aforementioned alcohol compound is an oligomeric or polymeric compound, it may have an appropriate molecular weight.

[0132] For example, the lower limit of the weight-average molecular weight of the oligomeric or polymeric polyol compound may be around 100 g / mol, 200 g / mol, 300 g / mol, 400 g / mol, 500 g / mol, 600 g / mol, 700 g / mol, 800 g / mol, or 900 g / mol, and the upper limit may be around 5000 g / mol, 4500 g / mol, 4000 g / mol, 3500 g / mol, 3000 g / mol, 2500 g / mol, 2000 g / mol, 1500 g / mol, 1000 g / mol, or 800 g / mol. The weight-average molecular weight may be less than or equal to any of the upper limits mentioned above, greater than or equal to any of the lower limits mentioned above, or greater than or equal to any of the lower limits mentioned above, while remaining within the range of less than or equal to any of the upper limits mentioned above.

[0133] By applying the oil-modified alcohol compounds described above, the desired physical properties can be more effectively secured.

[0134] The lower limit of the content of the oil-modified alcohol compound relative to 100 parts by weight of the oil-modified polyol compound is 10 parts by weight, 20 parts by weight, 30 parts by weight, 40 parts by weight, 50 parts by weight, 60 parts by weight, 70 parts by weight, 80 parts by weight, 90 parts by weight, 100 parts by weight, 110 parts by weight, 120 parts by weight, 130 parts by weight, 140 parts by weight, 150 parts by weight, 160 parts by weight, 170 parts by weight, 180 parts by weight, 190 parts by weight, 200 parts by weight, 210 parts by weight, 220 parts by weight, 230 parts by weight, 240 parts by weight, 250 parts by weight, and 260 parts by weight. The amount may be approximately 1,000 parts by weight, 270 parts by weight, 280 parts by weight, 290 parts by weight, or 300 parts by weight, and the upper limit may be approximately 1,000 parts by weight, 950 parts by weight, 900 parts by weight, 850 parts by weight, 800 parts by weight, 750 parts by weight, 700 parts by weight, 650 parts by weight, 600 parts by weight, 550 parts by weight, 500 parts by weight, 450 parts by weight, 400 parts by weight, 350 parts by weight, 300 parts by weight, 250 parts by weight, 200 parts by weight, 150 parts by weight, 100 parts by weight, 90 parts by weight, 80 parts by weight, 70 parts by weight, or 60 parts by weight. The aforementioned ratio may be less than or equal to any of the upper limits mentioned above, or greater than or equal to any of the lower limits mentioned above, or greater than or equal to any of the lower limits mentioned above, while remaining within the range of less than or equal to any of the upper limits mentioned above.

[0135] The aforementioned proportion may be changed in consideration of the overall composition of the resin composition and the desired physical properties.

[0136] The oil-modified polyol compound or alcohol compound may be synthesized by known synthesis methods. That is, the compound may be produced by reacting a known polyol compound with a compound that can introduce the hydrocarbon group corresponding to the oil-modified portion. Examples of compounds that can introduce the hydrocarbon group include saturated or unsaturated fatty acids, specifically butyric acid, caproic acid, 2-ethylhexanoic acid, caprylic acid, isononanoic acid, capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, linoleic acid, or oleic acid, but are not limited to these.

[0137] Furthermore, there are no particular restrictions on the type of polyol compound that reacts with the saturated or unsaturated fatty acid. For example, any suitable type of general polyol compound described later may be used, but the method is not limited to this.

[0138] The hydroxyl functional component may further contain a polyol compound different from the oil-modified polyol compound. In such cases, the polyol compound does not contain the aforementioned oil group, i.e., a linear or branched hydrocarbon group having three or more carbon atoms. For convenience, such a polyol compound may also be referred to as a general polyol compound in this specification.

[0139] The lower limit of the number of carbon atoms in the hydrocarbon group that does not contain general polyol compounds may be around 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, or 17, and the upper limit may be around 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, or 10. The number of carbon atoms may be less than or equal to any of the upper limits mentioned above, greater than or equal to any of the lower limits mentioned above, or greater than or equal to any of the lower limits mentioned above, while remaining within the range of less than or equal to any of the upper limits mentioned above. For example, the hydrocarbon group may be an alkyl group, alkenyl group, or alkynyl group having the number of carbon atoms mentioned above.

[0140] The aforementioned general polyol compound may contain two or more hydroxyl groups per molecule, and such polyol compound may be monomolecular, oligomeric, or polymeric compound. The number of hydroxyl groups contained in the general polyol compound is not particularly limited, but in one example, the lower limit of the number of hydroxyl groups contained in the general polyol compound may be about two or three per molecule, and the lower limit may be about 10, 9, 8, 7, 6, 5, 4, 3, or 2 per molecule. The number of hydroxyl groups may be less than or equal to any of the upper limits mentioned above, or greater than or equal to any of the lower limits mentioned above, or greater than or equal to any of the lower limits mentioned above, while remaining within the range of less than or equal to any of the upper limits mentioned above.

[0141] General polyol compounds may have various forms.

[0142] In one example, the general polyol compound may be a polyester polyol. As the polyester polyol, for example, so-called carboxylic acid polyols or caprolactone polyols may be used.

[0143] In one example, the polyester polyol may have a skeleton having repeating units represented by the following chemical formula 8.

[0144] [ka]

[0145] In chemical formula 8, X7 and X8 are independently single bonds or oxygen atoms, L3 may be an alkylene group, and p is any number.

[0146] In the above formula 8, the alkylene group may, in one example, be an alkylene 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.

[0147] If the polyester polyol is a polycaprolactone polyol, L3 in formula 8 may be a linear alkylene group having 5 carbon atoms.

[0148] Furthermore, in formula 8, p is any number representing the number of repeating units, and may be, for example, a number within the range of 1 to 25.

[0149] The lower limit of p in formula 8 may be approximately 1, 3, 5, 7, 9, 11, 13, 15, 17, 19, 21, or 23, and the upper limit may be approximately 25, 23, 21, 19, 17, 15, 13, 11, 9, 7, 5, or 3. The p may be less than or equal to any of the upper limits mentioned above, greater than or equal to any of the lower limits mentioned above, or greater than or equal to any of the lower limits mentioned above, while being within the range of less than or equal to any of the upper limits mentioned above.

[0150] The polyester polyol having the skeleton of formula 8 may be a so-called carboxylic acid polyol or a caprolactone polyol. Such polyol compounds may be formed by known methods. For example, the carboxylic acid polyol may be formed by reacting a carboxylic acid with a component containing a polyol (e.g., a diol or triol), and the caprolactone polyol may be formed by reacting caprolactone with a component containing a polyol (e.g., a diol or triol). The carboxylic acid may be a dicarboxylic acid.

[0151] In the polyol compound having the framework of formula 8, the hydroxyl group may be located at the end of the framework of formula 8, or at other locations on the polyester polyol.

[0152] The lower limit of the number of skeletons in the above formula 8 contained in a general polyol compound may be one or two, and the upper limit may be around 10, 9, 8, 7, 6, 5, 4, 3, 2, or 1. The number of skeletons may be less than or equal to any of the upper limits mentioned above, greater than or equal to any of the lower limits mentioned above, or greater than or equal to any of the lower limits mentioned above, while remaining within the range of less than or equal to any of the upper limits mentioned above.

[0153] The polyol compound having the polyester skeleton may have a linear or branched structure.

[0154] In the above, the linear structure is a structure in which a main chain containing the skeleton of formula 8 exists, and no other polymer chains are linked to the main chain, and the branched chain structure may be a form in which chains containing the skeleton of formula 8 are linked as side chains to the main chain containing the skeleton of formula 8. The number of chains containing the skeleton of formula 8 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.

[0155] As the general polyol compound mentioned above, polyols having alkanediol units, polyol units, and dicarboxylic acid units may be used in other examples. Such polyols may be mixtures of the alkanediol, polyol, and dicarboxylic acid, or reactants 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, or 1,6-hexanediol. Furthermore, examples of polyols include alkanes with 1 to 20 carbon atoms, 4 to 20 carbon atoms, 4 to 16 carbon atoms, or 4 to 12 carbon atoms, which are substituted with 3 to 10, 3 to 9, 3 to 8, 3 to 7, 3 to 6, 3 to 5, or 3 to 4 hydroxyl groups, such as trimethylolpropane. Examples of dicarboxylic acids include adipic acid, terephthalic acid, isophthalic acid, and sebacic acid. These types of polyol compounds are known by product names such as 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 from Kuraray.

[0156] As the general polyol mentioned above, a polyol with a weight-average molecular weight in the range of 100 g / mol to 5,000 g / mol may be used. The desired effect can be achieved more effectively through the application of such a polyol.

[0157] When the general polyol compound is included, the lower limit of the weight ratio of the general polyol compound to 100 parts by weight of the oil-modified polyol compound is 1 part by weight, 3 parts by weight, 5 parts by weight, 7 parts by weight, 10 parts by weight, 15 parts by weight, 20 parts by weight, 25 parts by weight, 30 parts by weight, 35 parts by weight, 40 parts by weight, 45 parts by weight, 50 parts by weight, 55 parts by weight, 60 parts by weight, 65 parts by weight, 70 parts by weight, 75 parts by weight, 80 parts by weight, 85 parts by weight. The amount may be approximately 100 parts by weight, 90 parts by weight, 95 parts by weight, or 100 parts by weight, and the upper limit may be approximately 200 parts by weight, 190 parts by weight, 180 parts by weight, 170 parts by weight, 160 parts by weight, 150 parts by weight, 140 parts by weight, 130 parts by weight, 120 parts by weight, 110 parts by weight, 100 parts by weight, 90 parts by weight, 80 parts by weight, 70 parts by weight, 60 parts by weight, 50 parts by weight, 40 parts by weight, 30 parts by weight, 20 parts by weight, or 10 parts by weight. The aforementioned ratio may be less than or equal to any of the upper limits mentioned above, or greater than or equal to any of the lower limits mentioned above, or greater than or equal to any of the lower limits mentioned above, while remaining within the range of less than or equal to any of the upper limits mentioned above.

[0158] In other examples, if the general polyol compound is included, the lower limit of the content ratio of the general polyol compound to 100 parts by weight of the total of the oil-modified polyol and the oil-modified alcohol may be approximately 1, 5, 10, 15, 20, 25, 30, 35, or 40 parts by weight, and the upper limit may be approximately 200, 190, 180, 170, 160, 150, 140, 130, 120, 110, 100, 90, 80, 70, 60, 50, 40, 30, 20, or 10 parts by weight. The aforementioned ratio may be less than or equal to any of the upper limits mentioned above, greater than or equal to any of the lower limits mentioned above, or greater than or equal to any of the lower limits mentioned above, while remaining within the range of less than or equal to any of the upper limits mentioned above.

[0159] The aforementioned proportions may be changed in consideration of the overall composition of the resin composition and the desired application.

[0160] The resin composition may also contain, as an additional component, a curing agent that reacts with the polyol compound and / or alcohol compound.

[0161] Various types of curing agents may be used, but in the case of a polyurethane composition, which is a resin composition, polyisocyanate may be used as the curing agent. The term polyisocyanate means a compound having two or more isocyanate groups. The lower limit of the number of isocyanate groups that polyisocyanate has may be around 2 or 3, and the upper limit may be around 10, 9, 8, 7, 6, 5, 4, 3, or 2. The number of isocyanate groups may be less than or equal to any of the upper limits mentioned above, or greater than or equal to any of the lower limits mentioned above, or greater than or equal to any of the lower limits mentioned above, while being within the range of less than or equal to any of the upper limits mentioned above.

[0162] The type of polyisocyanate used as a curing agent is not particularly limited, but non-aromatic polyisocyanates that do not contain aromatic groups may be used to ensure the desired physical properties.

[0163] Examples of polyisocyanate compounds that can be used include aliphatic polyisocyanates such as hexamethylene diisocyanate, trimethylhexamethylene diisocyanate, lysine diisocyanate, norbornane diisocyanate methyl, ethylene diisocyanate, propylene diisocyanate, or tetramethylene diisocyanate; alicyclic polyisocyanates such as transcyclohexanecyclohexane-1,4-diisocyanate, isophorone diisocyanate, bis(isocyanate methyl)cyclohexane diisocyanate, or dicyclohexylmethane diisocyanate; or one or more of the above-mentioned carbodiimide-modified polyisocyanates or isocyanurate-modified polyisocyanates. Furthermore, as the polyisocyanate, an addition reaction product of the above-mentioned diisocyanate and a polyol (e.g., trimethylolpropane) may be used. Additionally, a mixture of two or more of the exemplified compounds may be used.

[0164] The proportion of the polyisocyanate used may be adjusted considering the number of hydroxyl groups present in the hydroxyl-functional component contained in the resin composition and the physical properties after curing.

[0165] For example, the polyisocyanate may be included in the resin composition such that the equivalent ratio (OH / NCO) of the number of hydroxyl groups (OH) present in the hydroxyl functional component present in the resin composition to the number of isocyanate groups (NCO) present in the polyisocyanate is within the range of 50 to 1,000.

[0166] The method for calculating the aforementioned equivalent ratio (OH / NCO) is publicly known.

[0167] For example, if the resin composition is a two-component type, and the hydroxyl functional component is contained in the main component 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.

[0168]

number

[0169] In general formula 1, D1 is the density of the main component part, D2 is the density of the curing agent part, W1 is the weight ratio of the polyol compound or alcohol compound present in the main component part, OH% is the proportion of hydroxyl groups contained in the polyol compound or alcohol compound having the weight ratio of W1, W2 is the weight ratio of the polyisocyanate present in the curing agent part, NCO% is the proportion of isocyanate groups contained in the polyisocyanate having the weight ratio of W2, DN is 42 Da as the Dalton mass of the isocyanate group, and DO is 17 Da as the Dalton mass of the hydroxyl group.

[0170] W1 is the weight percentage (based on the total weight of the main component) of each polyol compound or alcohol compound present in the main component, and the OH% of the compound is the percentage of hydroxyl groups contained in 1 mole of each polyol compound or alcohol compound, which is obtained by dividing the product of the number of moles of hydroxyl groups contained in a single polyol compound or alcohol compound and the molar mass of the hydroxyl groups by the molar mass of the single polyol compound or alcohol compound, and then multiplying by 100.

[0171] Furthermore, in the above, W2 is the weight percentage of each polyisocyanate present in the curing agent part (based on the total weight of the curing agent part), and the NCO% of the compound is the percentage of NCO groups contained in 1 mole of each polyisocyanate compound, which is obtained by dividing the product of the number of moles of NCO groups contained in a single polyisocyanate compound and the molar mass of the NCO groups by the molar mass of the single polyisocyanate compound, and then multiplying by 100.

[0172] Furthermore, in the general formula 1 mentioned above, the Dalton mass is a constant.

[0173] The lower limit of the equivalent ratio (OH / NCO) may be around 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 around 1000, 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 aforementioned equivalent ratio may be less than or equal to any of the upper limits mentioned above, greater than or equal to any of the lower limits mentioned above, or greater than or equal to any of the lower limits mentioned above, while remaining within the range of less than or equal to any of the upper limits mentioned above.

[0174] The resin composition may further contain filler components. In this context, "filler component" refers to a component consisting solely of fillers, i.e., a component containing only fillers.

[0175] In one example, the filler component may include two or more fillers with different average particle sizes. In another example, the filler component may include three or more fillers with different average particle sizes, and may consist of three to six, three to five, three to four, or three fillers with different average particle sizes. That is, in one example, the filler component may consist only of the three to six, three to five, three to four, or three fillers with different average particle sizes.

[0176] In other examples, the filler component may represent at least two peaks in the volume curve of the particle size distribution measured using laser diffraction. In one example, the filler component may represent three or more peaks in the volume curve of the particle size distribution, or three to six, three to five, three to four, or three peaks. For example, the range of filler components representing three peaks does not include filler components representing one, two, or four or more peaks.

[0177] In this application, the average particle size of the filler refers to the particle size at which the volume accumulation in the volume curve of the particle size distribution measured by laser diffraction reaches 50%, and this is sometimes called the median diameter. In other words, in this application, the particle size distribution is determined on a volume basis through the aforementioned laser diffraction method, and the particle size at the point where the cumulative value reaches 50% in the accumulation curve with the total volume set to 100% is defined as the average particle size. Such an average particle size may also be called the median particle size or D50 particle size in other examples.

[0178] Therefore, the two types of fillers having different average particle sizes as described above refer to fillers with different particle sizes at the point where the cumulative value in the volume curve of the particle size distribution reaches 50%.

[0179] Typically, when two or more fillers with different average particle sizes are mixed to form a filler component, the volume curve of the particle size distribution measured using laser diffraction for the filler component will show peaks corresponding to the types of fillers mixed. Therefore, for example, if three fillers with different average particle sizes are mixed to form a filler component, the volume curve of the particle size distribution measured using laser diffraction for that filler component will show three peaks.

[0180] The filler component of the resin composition of this application 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 its cured body to exhibit the aforementioned thermal conductivity.

[0181] In one example, the filler component may include a first filler with an average particle size of at least 60 μm to 200 μm, a second filler with an average particle size in the range of 10 μm to 30 μm, and a third filler with an average particle size of 5 μm or less.

[0182] The lower limit of the average particle size of the first filler may be around 62 μm, 64 μm, 66 μm, or about 68 μm, and the upper limit may be around 200 μm, 195 μm, 190 μm, 185 μm, 180 μm, 175 μm, 170 μm, 165 μm, 160 μm, 155 μm, 150 μm, 145 μm, 140 μm, 135 μm, 130 μm, 125 μm, about 120 μm, 115 μm, 110 μm, 105 μm, 100 μm, 95 μm, 90 μm, 85 μm, 80 μm, or about 75 μm. The average particle size of the first filler may be less than or equal to any of the upper limits mentioned above, greater than or equal to any of the lower limits mentioned above, or greater than or equal to any of the lower limits mentioned above, while remaining within the range of less than or equal to any of the upper limits mentioned above.

[0183] The lower limit of the average particle size of the second filler may be approximately 10 μm, 12 μm, 13 μm, 14 μm, 15 μm, 16 μm, 17 μm, 18 μm, 19 μm, or 20 μm, and the upper limit may be approximately 29 μm, 28 μm, 27 μm, 26 μm, 25 μm, 24 μm, 23 μm, 22 μm, 21 μm, or approximately 20 μm. The average particle size of the second filler may be less than or equal to any of the upper limits mentioned above, greater than or equal to any of the lower limits mentioned above, or greater than or equal to any of the lower limits mentioned above, while remaining within the range of less than or equal to any of the upper limits mentioned above.

[0184] The lower limit of the third filler may be approximately 0.01 μm, 0.1 μm, about 0.5 μm, 1 μm, 1.5 μm, or 2 μm, and the upper limit may be approximately 5 μm, 4.5 μm, about 4 μm, 3.5 μm, 3 μm, 2.5 μm, or 2 μm. The average particle size of the third filler may be less than or equal to any of the upper limits mentioned above, greater than or equal to any of the lower limits mentioned above, or greater than or equal to any of the lower limits mentioned above, while being within the range of less than or equal to any of the upper limits mentioned above.

[0185] In the filler component, the ratio (D1 / D3) of the average particle size of the first filler (D1) to the average particle size of the third filler (D3) may be within the range of 25 to 300.

[0186] In one example, the third filler may be the filler with the smallest average particle size among the fillers included in the filler component, if the filler component includes two or more fillers with different average particle sizes, and the first filler may be the filler with the largest average particle size among the fillers included in the filler component, if the filler component includes two or more fillers with different average particle sizes. The particle size ratio can be satisfied in this state.

[0187] The lower limit of the aforementioned ratio (D1 / D3) may be around 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 40, 50, 60, 70, 80, 90, 100, 110, 120, 130, 140, 150, 160, 170, 180, 190, 200, 210, 220, 230, or 235, and the upper limit may be around 300, 290, 280, 270, 260, 250, 240, 220, 200, 180, 160, 140, 120, 100, 95, 90, 85, 80, 75, 70, 65, or 60. The aforementioned ratio may be less than or equal to any of the upper limits mentioned above, greater than or equal to any of the lower limits mentioned above, or greater than or equal to any of the lower limits mentioned above, while remaining within the range of less than or equal to any of the upper limits mentioned above.

[0188] In the filler component, the lower limit of the ratio (D1 / D2) between the average particle size (D1) of the first filler and the average particle size (D2) of the second filler may be approximately 3, 3.1, 3.2, 3.3, 3.4, or 3.5, and may also be approximately 20, 18, 17, 16, 15, 14, 13, 12, 11, 10, 9, 8, 7, 6, 5, or 4. The ratio may be less than or equal to any of the upper limits mentioned above, greater than or equal to any of the lower limits mentioned above, or greater than or equal to any of the lower limits mentioned above, while remaining within the range of less than or equal to any of the upper limits mentioned above.

[0189] As fillers, for example, 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), calcium hydroxide (Ca(OH)2), hydromagnesite and / or bohemite may be used. Such fillers are advantageous in satisfying the thermal conductivity range mentioned above, and furthermore, the insulation properties mentioned above can also be satisfied through the application of ceramic fillers.

[0190] The upper limit of the proportion of the filler component in the resin composition may be approximately 99% by weight, 98% by weight, 97% by weight, 96% by weight, 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, 89.0% by weight, 88.5% by weight, or 88.0% by weight, and the lower limit may be approximately 70% by weight, 71% by weight, 72% by weight, 73% by weight, 74% by weight, approximately 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 aforementioned ratio may be less than or equal to any of the upper limits mentioned above, greater than or equal to any of the lower limits mentioned above, or greater than or equal to any of the lower limits mentioned above, while remaining within the range of less than or equal to any of the upper limits mentioned above.

[0191] The content of the filler component is, in the case of a one-component resin composition, a ratio based on the total weight of the resin composition; in the case of a two-component resin composition, it may be a ratio based on the total weight of the main component part and the curing agent part of the two-component resin composition, or it may be a ratio based on the total weight of the main component or the curing agent part alone.

[0192] When the resin composition is a two-component resin composition, it is appropriate to divide the filler component to be applied to the final cured product into substantially equal amounts and introduce them into the main component and the curing agent parts, respectively.

[0193] In addition to the aforementioned thermally conductive filler, the filler component may include various other types of fillers as needed. For example, carbon fillers such as graphite, fumed silica, or clay may be used.

[0194] The resin composition may also contain other necessary components in addition to the components mentioned above.

[0195] In one example, the resin composition may further contain a plasticizer. As mentioned above, this application can ensure low adhesion to specific materials without applying a plasticizer, but a small amount of plasticizer may be applied as needed.

[0196] There are no particular restrictions on the types of plasticizers that can be applied. For example, phthalate-based plasticizers such as dioctyl phthalate (DOP), dibutyl phthalate (DBP), butyl benzyl phthalate (BBP), diisononyl phthalate (DINP), or polyethylene terephthalate (PET), as well as adipate-based plasticizers such as dioctyl adipate (DOA) or diisononyl adipate (DINA), fatty acid-based plasticizers, phosphate-based plasticizers, or polyester-based plasticizers may be used.

[0197] If a plasticizer is included, its proportion may be adjusted according to the purpose. For example, if the plasticizer is included, the lower limit of the weight ratio of the plasticizer to 100 parts by weight of the oil-modified polyol compound may be approximately 0.5 parts by weight, 1.5 parts 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, 10 parts by weight, 15 parts by weight, 20 parts by weight, 25 parts by weight, 30 parts by weight, 35 parts by weight, 40 parts by weight, 45 parts by weight, 50 parts by weight, 100 parts by weight, 150 parts by weight, 200 parts by weight, 250 parts by weight, or 300 parts by weight, and the upper limit may be 500 parts by weight. The proportion may be approximately 1 part, 450 parts by weight, 400 parts by weight, 350 parts by weight, 300 parts by weight, 250 parts by weight, 200 parts by weight, 150 parts by weight, 100 parts by weight, 90 parts by weight, 80 parts by weight, 70 parts by weight, 60 parts by weight, 50 parts by weight, 40 parts by weight, 30 parts by weight, 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, 7 parts by weight, 6 parts by weight, 5 parts by weight, 4 parts by weight, 3 parts by weight, 2 parts by weight, or 1 part by weight. The proportion may be less than or equal to any of the upper limits mentioned above, greater than or equal to any of the lower limits mentioned above, or greater than or equal to any of the lower limits mentioned above, while remaining within the range of less than or equal to any of the upper limits mentioned above.

[0198] In other examples, if the plasticizer is included, the lower limit of the proportion of the plasticizer per 100 parts by weight of the total of the oil-modified polyol and oil-modified alcohol (oil-modified component) may be approximately 0.5 parts by weight, 1.5 parts by weight, 2 parts by weight, 5 parts by weight, 10 parts by weight, 15 parts by weight, 20 parts by weight, 25 parts by weight, 30 parts by weight, 50 parts by weight, 60 parts by weight, 70 parts by weight, 80 parts by weight, 90 parts by weight, 100 parts by weight, 110 parts by weight, 120 parts by weight, 130 parts by weight, or 140 parts by weight, and the upper limit This may be approximately 400 parts by weight, 350 parts by weight, 300 parts by weight, 250 parts by weight, 200 parts by weight, 150 parts by weight, 100 parts by weight, 90 parts by weight, 80 parts by weight, 70 parts by weight, 60 parts by weight, 50 parts by weight, 40 parts by weight, 30 parts by weight, 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, 7 parts by weight, 6 parts by weight, 5 parts by weight, 4 parts by weight, 3 parts by weight, 2 parts by weight, or 1 part by weight. The aforementioned ratio may be less than or equal to any of the upper limits mentioned above, or greater than or equal to any of the lower limits mentioned above, or greater than or equal to any of the lower limits mentioned above, while remaining within the range of less than or equal to any of the upper limits mentioned above.

[0199] The aforementioned proportions may be changed in consideration of the overall composition of the resin composition and the desired application.

[0200] The resin composition may also contain additional components as needed, in addition to the components described above. Examples of additional components include catalysts that assist or accelerate the curing reaction, viscosity modifiers for adjusting viscosity, such as increasing or decreasing viscosity, or for adjusting viscosity by shear force (e.g., thixotropy imparters, diluents, etc.), dispersants, surface treatment agents, or coupling agents.

[0201] The resin composition may further contain flame retardants or flame retardant aids. In this case, known flame retardants may be used without particular limitation, for example, solid-phase filler-type flame retardants or liquid flame retardants may be applied.

[0202] Examples of flame retardants include organic flame retardants such as melamine cyanurate and inorganic flame retardants such as magnesium hydroxide. When a large amount of filler is used to fill the resin layer, liquid-type flame retardants (such as TEP, triethyl phosphate or TCPP, tris(1,3-chloro-2-propyl)phosphate) may be used. In addition, a silane coupling agent capable of enhancing flame retardancy may be added.

[0203] As mentioned above, the resin composition may be a one-component composition or a two-component composition. In the case of a two-component composition, each of the aforementioned components of the resin composition may be included separately as a main component part and a curing agent part, which are physically separated.

[0204] This application relates, in one example, to a composition (two-component composition) in which the resin composition is composed of a two-component resin composition.

[0205] Such a two-component composition may include at least a main component and a curing agent, and the main component and curing agent may be physically separated from each other. When the physically separated main component and curing agent are mixed, a curing reaction is initiated, and as a result, polyurethane may be formed.

[0206] In a two-component composition, the main component may contain at least an oil-modified polyol compound among the hydroxyl functional components, and the curing agent component may contain at least the polyisocyanate.

[0207] If the resin composition contains the aforementioned oil-modified alcohol compound and / or general polyol compound, this compound may, for example, be included in the main component part.

[0208] Furthermore, the filler component may be contained in either the main component or the hardener component, or in both the main component and the hardener component. If the filler component is contained in both the main component and the hardener component, the main component and the hardener component may contain the same amount of the filler component.

[0209] *Other components such as catalysts, plasticizers, and flame retardants may be included in the main component and / or curing agent part as needed.

[0210] Furthermore, in the two-component composition, the volume ratio (P / N) of the volume of the main component part (P) to the volume of the curing agent part (N) may be in the range of approximately 0.8 to 1.2.

[0211] Such two-component compositions or their cured products can also exhibit the aforementioned adhesion to aluminum and polyester, thermal conductivity, hardness, curvature, insulation, flame retardancy, specific gravity, shrinkage rate, coefficient of thermal expansion, and / or 5% weight loss temperature in thermogravimetric analysis (TGA).

[0212] This application further relates to a product comprising the resin composition or a cured product thereof. The resin composition or cured product of this application may be usefully applied as a heat dissipation material. Therefore, the product may include heat-generating components. The term heat-generating components means components that dissipate heat during use, and their type is not particularly limited. Typical heat-generating components include various electrical / electronic products such as battery cells, battery modules, or battery packs.

[0213] The product of this application may include, for example, the heat-generating component and the resin composition (or the two-component composition) or a cured product thereof that is adjacent to the heat-generating component.

[0214] The specific method of constructing the product of this application is not particularly limited, and when the resin composition or two-component composition or its cured product of this application is applied as a heat dissipation material, the product can be constructed in various known ways. [Effects of the Invention]

[0215] This application may provide a resin composition or its cured product that exhibits high thermal conductivity and low adhesive strength to a predetermined adherend. Furthermore, this application may achieve the low adhesive strength without using adhesive strength-modifying components such as plasticizers, or with the proportion of such components minimized. This application may further provide a product containing the curable composition or its cured product. [Brief explanation of the drawing]

[0216] [Figure 1] Figure 1 shows the analysis results of the hydroxy-functionalized component synthesized in Production Example 1. [Figure 2] Figure 2 shows the analysis results of the hydroxy-functionalized component synthesized in Production Example 2. [Modes for carrying out the invention]

[0217] The present application will be specifically described through the following embodiments, but the scope of this application is not limited by the embodiments described below.

[0218] The cured bodies mentioned below were all formed by mixing the main component and curing agent parts of the resin compositions of the two-component examples to satisfy the OH / NCO equivalent ratio described in each example, and then holding them at room temperature for about 24 hours.

[0219] 1. Thermal conductivity The thermal conductivity of the resin composition (curable composition) or its cured product was measured using the Hot-Dist method in accordance with the ISO 22007-2 standard. Specifically, a mixture of the main component and hardener component of the example or comparative example, composed in a two-component type with a volume ratio of 1:1, was placed in a mold approximately 7 mm thick, and the thermal conductivity was measured in the through-plane direction using a HotDisk device. As specified in the aforementioned standard (ISO 22007-2), the HotDisk device is a device that can confirm thermal conductivity by measuring temperature changes (changes in electrical resistance) while a sensor consisting of a double spiral structure of nickel wire is heated, and the thermal conductivity was measured in accordance with this standard.

[0220] 2. Measurement of adhesive strength to polyester The adhesive strength to polyester was evaluated for specimens prepared by adhering a PET (polyethylene terephthalate) film to an aluminum plate. The PET film used was approximately 10 mm wide and 200 mm long, while 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. The specimens were then prepared by holding them at room temperature (approximately 25°C) for approximately 24 hours. During this process, approximately 100 mm of the PET film's total width and length was adhered to the aluminum plate via the resin composition. With the aluminum plate of the specimen fixed, the adhesive strength was measured while peeling the PET film from the aluminum plate in the longitudinal direction. The aforementioned adhesion was performed by applying the resin composition (a mixture of the main component and the hardener in a volume ratio of 1:1) to the aluminum plate so that the thickness after curing would be approximately 2 mm, then adhering the PET film to the layer of the resin composition, and holding it at room temperature (approximately 25°C) for approximately 24 hours to cure the resin composition. The aforementioned peeling was performed at a peeling speed of approximately 0.5 mm / min and a peeling angle of 180 degrees until the PET film was completely peeled off.

[0221] 3. Measurement of adhesive strength to aluminum An uncured resin composition (a mixture of a main component and a hardener component) was applied to the center of two aluminum substrates, each measuring 2 cm horizontally and 7 cm vertically, to create a layer approximately 2 cm horizontally and 2 cm vertically. The two aluminum substrates, each measuring 2 cm horizontally and 7 cm vertically, were then attached to the coating layer, and the resin composition was cured while maintaining this state. The two aluminum substrates were attached at a 90-degree angle to each other. Subsequently, with the upper aluminum substrate fixed, the lower aluminum substrate was pressed at a speed of 0.5 mm / min, and the force required to separate the lower aluminum substrate was measured. The maximum force measured during this process was divided by the area of ​​the specimen to determine the adhesive strength to aluminum.

[0222] 4. Measurement of hardness The hardness of the cured resin composition was measured according to ASTM D2240 and JIS K 6253 standards. An ASKER durometer hardness instrument was used. A load of 1 kg or more (approximately 1.5 kg) was applied to the surface of a flat sample (resin layer) to measure the initial hardness, and the hardness was evaluated by confirming the stabilized measurement value after 15 seconds.

[0223] 5. Measurement of the radius of curvature The radius of curvature of the hardened material was evaluated using hardened materials with widths of 1 cm, length, and thickness of 1 cm, 10 cm, and 2 mm, respectively. The radius of curvature is the minimum radius of a cylinder on which no cracks occur when the hardened material is attached to a cylinder of various radii and bent along the longitudinal direction.

[0224] 6. Measurement of weight-average molecular weight The weight-average molecular weight (Mw) was measured using GPC (Gel permeation chromatography). Specifically, the weight-average molecular weight (Mw) was measured by placing the sample to be analyzed in a 5 mL vial, diluting it with a THF (tetrahydrofuran) solvent to a concentration of approximately 1 mg / mL, and then filtering the calibration standard sample and the analysis sample through a syringe filter (pore size: 0.45 μm). As the analysis program, ChemStation of Agilent technologies was used, and the weight-average molecular weight (Mw) could be determined by comparing the elution time of the sample with the calibration curve.

[0225] <GPC Measurement Conditions> Instrument: 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

[0226] Production Example 1. The hydroxy group-functional component (A) which becomes the oil-modified polyol compound of Chemical Formula A below was produced as follows.

[0227] [Chemical Formula]

[0228] In Chemical Formula A, n and m each exceed 0, and their total is approximately 4.8.

[0229] A polycaprolactone polyol (Capa 3031 from Perstorp) and a saturated fatty acid, isononanoic acid, were mixed in a weight ratio of 1:0.53 (Capa 3031: isononanoic acid). Next, a catalyst (Tin(II) 2-ethylhexanoate (Sigma-Aldrich)) was added at a rate of 0.1 parts by weight per 100 parts by weight of the mixture, and the mixture was held at 150°C for 30 minutes with stirring under inert gas purging conditions. Then, a small amount of azeotropic xylene was added, the temperature was raised to 200°C, and the reaction was carried out for more than 3 hours. After that, the pressure was reduced to below 80 Torr to remove the xylene and unreacted products. After the reaction mixture was cooled, it was filtered to obtain the target product (compound A).

[0230] GPC analysis performed on the aforementioned target substance revealed that the weight-average molecular weight was approximately 876 g / mol. Figure 1 shows the results of the GPC analysis performed on the aforementioned target substance.

[0231] Manufacturing example 2. A hydroxyl group functional component (B), which is an oil-modified polyol compound represented by the following formula B, was produced by the method described below.

[0232] [ka]

[0233] In chemical formula B, n is approximately 4, R4 is a substituent in chemical formula B-1 below, and R3 is a substituent in chemical formula B-2 below.

[0234] [ka]

[0235] In chemical equation B-1, n is approximately 4.

[0236] [ka]

[0237] The compound shown in formula C below (PPG, manufacturer: Perstorp, product name: Polyol3380) and the saturated fatty acid isononanoic acid were mixed in a flask in a weight ratio of 1:0.38 (compound C: isononanoic acid).

[0238] [ka]

[0239] In the compound C, n is approximately 4, and R4 is the substituent in the compound C-1 below.

[0240] [ka]

[0241] In chemical equation C-1, n is approximately 4.

[0242] To the aforementioned mixture, a catalyst (Tin(II)2-ethylhexanoate (Sigma-Aldrich)) was added at a rate of 0.3 parts by weight per 100 parts by weight of the total mixture. The mixture was then stirred and held at 150°C for 30 minutes under inert gas purging conditions. Next, a small amount of xylene, an azeotropic solution, was added, and the temperature was raised to 190°C for more than 10 hours to allow the reaction to proceed. The pressure was then reduced to below 40 Torr for more than 1 hour to remove the xylene and unreacted materials. The reaction mixture was cooled and filtered to obtain the target product.

[0243] GPC analysis performed on the aforementioned target substance revealed that its weight-average molecular weight was approximately 800 g / mol. Figure 2 shows the results of the GPC analysis performed on the aforementioned target substance.

[0244] Example 1. Manufacturing of the main ingredient The main component was prepared by mixing the hydroxyl group functional component (B), filler component, and plasticizer (diisononyl adipate) from Production Example 2 in a weight ratio of 10:89:1 (component (B):filler component:plasticizer). The filler component was prepared 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 weight ratio during the mixing was approximately 6:2:2 (first alumina filler:second alumina filler:third alumina filler).

[0245] Manufacturing of the hardening agent part Polyisocyanate (Vencorex, Tolonate HDT-LV2) was used as the curing agent. The curing agent part was prepared by mixing the polyisocyanate, a filler component, and a plasticizer (diisononyl adipate) in a weight ratio of 5:5:90 (polyisocyanate:filler component:plasticizer). The same filler component used in the main component part was used as the filler component.

[0246] Manufacturing of resin compositions and cured products The main component part and the curing agent part were prepared separately to produce a resin composition (curable composition). After mixing the main component and the curing agent part, the mixture was kept at room temperature to form a cured body. The mixing was performed so that the equivalent ratio (OH / NCO) of hydroxyl groups (OH) present in the main component part to isocyanate groups (NCO) present in the curing agent part was approximately 100.

[0247] Example 2. Similar to Example 1, a main component part and a curing agent part were prepared separately to produce a resin composition (curable composition). After mixing the main component and the curing agent part, the mixture was kept at room temperature to form a cured body. The mixing was performed such that the equivalent ratio (OH / NCO) of hydroxyl groups (OH) present in the main component part to isocyanate groups (NCO) present in the curing agent part was approximately 170.

[0248] Example 3. Manufacturing of the main ingredient The hydroxy group-functional component (A), filler component, and plasticizer (diisononyl adipate) of Production Example 1 were mixed at a weight ratio of 9.7:89:1.3 (component (A): filler component: plasticizer) to produce the main agent part. The same filler component as in Example 1 was used as the filler component.

[0249] Manufacturing of the hardening agent part Polyisocyanate (Vencorex, Tolonate HDT-LV2) was used as the curing agent. The polyisocyanate, filler component, and plasticizer (diisononyl adipate) were mixed at a weight ratio of 5:5:90 (polyisocyanate: filler component: plasticizer) to produce the curing agent part. The same filler component as in Example 1 was used as the filler component.

[0250] Manufacturing of resin compositions The main agent part and the curing agent part were each prepared to produce a resin composition (curable composition). After mixing the main agent and the curing agent parts, they were held at room temperature to form a cured body. The mixing was carried out so that the equivalent ratio (OH / NCO) of the hydroxy group (OH) present in the main agent part and the isocyanate group (NCO) present in the curing agent part was about 100.

[0251] Example 4. A resin composition (curable composition) was produced by preparing the main agent part and the curing agent part in the same manner as in Example 3. After mixing the main agent and the curing agent parts, they were held at room temperature to form a cured body. The mixing was carried out so that the equivalent ratio (OH / NCO) of the hydroxy group (OH) present in the main agent part and the isocyanate group (NCO) present in the curing agent part was about 170.

[0252] Example 5. Manufacturing of the main ingredient The main component was prepared by mixing the hydroxyl group functional component (A) from Production Example 1, a general polyol compound (Kuraray, F-2010), a filler component, and a plasticizer (diisononyl adipate) in a weight ratio of 11.4:1.1:87:0.5 (component (A): general polyol compound: filler component: plasticizer). The same filler component as in Example 1 was used.

[0253] Manufacturing of the hardening agent part Polyisocyanate (Vencorex, Tolonate HDT-LV2) was used as the curing agent. The curing agent part was prepared by mixing the polyisocyanate, filler component, and plasticizer (diisononyl adipate) in a weight ratio of 5:5:90 (polyisocyanate:filler component:plasticizer). The same filler component as in Example 1 was used.

[0254] Manufacturing of resin compositions The main component part and the curing agent part were prepared separately to produce a resin composition (curable composition). After mixing the main component and the curing agent part, the mixture was kept at room temperature to form a cured body. The mixing was performed so that the equivalent ratio (OH / NCO) of hydroxyl groups (OH) present in the main component part to isocyanate groups (NCO) present in the curing agent part was approximately 179.

[0255] Example 6. Similar to Example 5, a main component part and a curing agent part were prepared separately to produce a resin composition (curable composition). After mixing the main component and the curing agent part, the mixture was kept at room temperature to form a cured body. The mixing was performed such that the equivalent ratio (OH / NCO) of hydroxyl groups (OH) present in the main component part to isocyanate groups (NCO) present in the curing agent part was approximately 157.

[0256] Example 7. Similar to Example 5, a main component part and a curing agent part were prepared separately to produce a resin composition (curable composition). After mixing the main component and the curing agent part, the mixture was kept at room temperature to form a cured body. The mixing was performed such that the equivalent ratio (OH / NCO) of hydroxyl groups (OH) present in the main component part to isocyanate groups (NCO) present in the curing agent part was approximately 140.

[0257] Example 8. Manufacturing of the main ingredient The main component was prepared by mixing the hydroxyl group functional component (A) from Production Example 1, a general polyol compound (Kuraray, F-2010), a filler component, and a plasticizer (diisononyl adipate) in a weight ratio of 7.4:3.2:87:2.4 (component (A): general polyol: filler component: plasticizer). The same filler component as in Example 1 was used.

[0258] Manufacturing of the hardening agent part Polyisocyanate (Vencorex, Tolonate HDT-LV2) was used as the curing agent. The curing agent part was prepared by mixing the polyisocyanate, filler component, and plasticizer (diisononyl adipate) in a weight ratio of 5:5:90 (polyisocyanate:filler component:plasticizer). The same filler component as in Example 1 was used.

[0259] Manufacturing of resin compositions The main component part and the curing agent part were prepared separately to produce a resin composition (curable composition). After mixing the main component and the curing agent part, the mixture was kept at room temperature to form a cured body. The mixing was performed so that the equivalent ratio (OH / NCO) of hydroxyl groups (OH) present in the main component part to isocyanate groups (NCO) present in the curing agent part was approximately 170.

[0260] Example 9. Similar to Example 8, a main component part and a curing agent part were prepared separately to produce a resin composition (curable composition). After mixing the main component and the curing agent part, the mixture was kept at room temperature to form a cured body. The mixing was performed such that the equivalent ratio (OH / NCO) of hydroxyl groups (OH) present in the main component part to isocyanate groups (NCO) present in the curing agent part was approximately 140.

[0261] The results of the physical property evaluation for each of the above embodiments are summarized in Table 1 below.

[0262] [Table 1]

Claims

1. The product comprises a polyol compound having at least one branched hydrocarbon group at its terminus, a curing agent, and a filler. The branched hydrocarbon group has five or more carbon atoms, The polyol compound has a polyester skeleton or a polyether skeleton, The polyester skeleton has a skeleton formed by reacting a component containing a dicarboxylic acid and a polyol, or a polycaprolactone skeleton. The polyether skeleton has a skeleton having repeating units represented by the following formula 5, The curing agent comprises polyisocyanate, 【Chemistry 1】 In equation 5, X ４ and X ５ Each is independently a single bond or an oxygen atom, L ２ A curable composition in which is an alkylene group having 1 to 20 carbon atoms, and m is a number in the range of 3 to 25.

2. Adhesion strength to aluminum is 0.1 N / mm² ２ The following hardened body is formed, The curable composition according to claim 1, wherein the adhesive force is measured by pressing an aluminum substrate at a speed of 0.5 mm / min and measuring the force while the aluminum substrate is separated from the cured body, and dividing the maximum force measured in that process by the area of ​​the test piece.

3. A cured body is formed with an adhesive strength to the surface of polyester of 100 gf / cm (98.0665 N / m) or less. The curable composition according to claim 1, wherein the adhesive strength is measured by completely peeling the polyester film from the cured body at a peeling speed of 0.5 mm / min and a peeling angle of 180 degrees.

4. The curable composition according to claim 1, which forms a cured body with a Shore hardness of 95 or less.

5. The curable composition according to claim 1, wherein the hydrocarbon group is an alkyl group, an alkenyl group, or an alkynyl group.

6. The curable composition according to claim 1, wherein the polyol compound contains at least one substituent of the following chemical formula 1 at its terminal end. 【Chemistry 2】 In chemical formula 1, R is a branched hydrocarbon group with five or more carbon atoms.

7. The curable composition according to claim 1, wherein the polyol compound comprises a polyol compound having a weight-average molecular weight in the range of 100 g / mol to 3000 g / mol.

8. The curable composition according to claim 1, further comprising a polyol compound that does not have a branched hydrocarbon group having five or more carbon atoms.

9. The curable composition according to claim 8, wherein the polyol compound that does not have a branched hydrocarbon group having five or more carbon atoms is a polycaprolactone polyol or a polyol having alkanediol units, polyol units and dicarboxylic acid units.

10. The curable composition according to claim 1, further comprising a plasticizer.

11. The curable composition according to claim 1, wherein the filler is aluminum hydroxide, magnesium hydroxide, calcium hydroxide, hydromagnesite, magnesia, alumina, aluminum nitride, boron nitride, silicon nitride, silicon carbide, zinc oxide, or beryllium oxide.

12. A polyol compound having at least one branched hydrocarbon group at its terminus and a main component part containing a filler, and It includes a hardening agent component and a hardening agent part containing a filler, The branched hydrocarbon group has five or more carbon atoms, The polyol compound has a polyester skeleton or a polyether skeleton, The polyester skeleton has a skeleton formed by reacting a component containing a dicarboxylic acid and a polyol, or a polycaprolactone skeleton. The polyether skeleton has a skeleton having repeating units represented by the following formula 5, The curing agent comprises polyisocyanate, 【Transformation 3】 In equation 5, X ４ and X ５ Each is independently a single bond or an oxygen atom, L ２ A two-component composition in which is an alkylene group having 1 to 20 carbon atoms, and m is a number in the range of 3 to 25.

13. A product comprising a heat-generating component and a cured body of a curable composition according to any one of claims 1 to 11 or a two-component composition according to claim 12, located adjacent to the heat-generating component.

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