KR20230064718A - Resin Composition - Google Patents

Abstract

The application relates to curable composition and uses thereof. The curable composition of the present application can provide a curable composition which can be applied to products which generate heat during driving or maintenance and used as a material capable of handling said heat. The curable composition of the present application can be applied to a product in which a plurality of heat-generating elements are integrated, and the heat generated from the elements can be efficiently treated while maintaining the temperature of the product uniformly. In addition, the curable composition of the present application can be applied to the above products to prevent or minimize the effect of such heat generation, explosion, or ignition on other adjacent elements even if abnormal heat generation, explosion, or ignition occurs in any one element among the plurality of elements. The curable composition of the present application can also stably perform the above functions over a long period of time.

Description

Curable composition {Resin Composition}

This application relates to curable compositions and uses thereof.

The importance of technology for handling heat generated by products is increasing. One of the typical methods of treating heat is to discharge heat generated from a product to the outside by using a material with excellent thermal conductivity or to dissipate the generated heat by using a cooling medium.

It is a difficult problem to handle heat in a product composed of elements that generate heat (heating elements).

For example, a battery module or battery pack includes a plurality of battery cells or a plurality of battery modules, which are positioned relatively adjacent to each other. Therefore, heat generated from one battery cell or battery module affects other adjacent devices, and in some cases may cause problems such as chain ignition or chain explosion.

Therefore, in these products, it is necessary to prevent heat, explosion, or fire generated from one element from affecting other adjacent elements.

Depending on the product, it is necessary to maintain a uniform temperature throughout the driving or maintenance process. Therefore, in a product composed of a plurality of heating elements gathered as described above, the temperature of the entire product can be maintained uniformly during the driving or maintenance process, and abnormal heat generated from one heating element, explosion or fire can be prevented from other elements as much as possible. A technology that can process it without propagating it is required.

This application relates to curable compositions and uses thereof. The curable composition of the present application may be applied to a product that generates heat during driving or maintenance to provide a curable composition that can be used as a material capable of treating the heat. The curable composition of the present application is applied to a product in which a plurality of elements generating heat are integrated, and the heat generated by the element can be efficiently treated while maintaining a uniform temperature of the product. In addition, even when the curable composition of the present application is applied to the product as described above and abnormal heat generation, explosion, or ignition occurs in any one element among the plurality of elements, such heat generation, explosion, or ignition is transmitted to other adjacent elements. impact can be prevented or minimized. The curable composition of the present application can also stably perform the above functions over a long period of time.

This application may also provide a cured body formed by the curable composition as above or a use of the curable composition or the cured body.

Among the physical properties mentioned in this specification, the physical properties in which the temperature affects the physical properties are the physical properties measured at room temperature unless otherwise specified.

As used herein, the term room temperature is a natural temperature that is not heated and cooled, for example, any one temperature within the range of about 10 ° C to 30 ° C, for example, about 15 ° C, about 18 ° C, about 20 ° C, It means a temperature of about 23 ° C or about 25 ° C. In addition, in this specification, unless otherwise specified, the unit of temperature is °C.

Among the physical properties mentioned in this specification, when pressure affects the result, the corresponding physical property is a physical property measured at atmospheric pressure, unless otherwise specified. The term normal pressure is natural pressure that is not pressurized and reduced, and usually refers to about 1 atm (about 700 to 800 mmHg) as normal pressure.

Among the physical properties mentioned in this specification, when humidity affects the result, unless otherwise specified, the corresponding physical property is a physical property measured under humidity that is not particularly controlled at room temperature and normal pressure.

This application is directed to curable compositions. The term curable composition is a composition capable of being cured. Curing is a phenomenon in which a composition hardens by a physical and/or chemical reaction.

The curable composition may be an energy ray curing type, a moisture curing type, a heat curing type, a room temperature curing type, or a hybrid curing type in which two or more of the curing methods are applied.

The energy ray curing type is a method of irradiating the composition with energy rays such as ultraviolet rays, a method of maintaining the composition under appropriate moisture in the case of a moisture curing type, a method of applying appropriate heat to the composition in the case of a heat curing type, or a method of applying room temperature The curable composition can be cured in a way to maintain the curable composition, and in the case of a hybrid curing type, two or more of the above-described methods can be applied simultaneously or applied stepwise to cure the curable composition. In one example, the curable composition of the present application may be curable at least at room temperature. For example, the curable composition of the present application can be cured without separate energy ray irradiation and heat application in a state maintained at room temperature.

The curable composition of the present application may be a one-component curable composition or a two-component curable composition. A one-component curable composition is a composition in which components necessary for curing are stored in a mixed state, and a two-component curable composition is a composition in which components necessary for curing are stored in a physically separated state. A two-component curable composition usually includes a so-called main part and a curing agent part, and the main subject and the curing agent part are mixed for curing. When the curable composition of the present application is a two-part curable composition, the curable composition may be a main part or a curing agent part of the two-component curable composition, or a mixture of the main part and the curing agent part.

The curable composition may form a cured body exhibiting latent heat at a predetermined temperature (latent heat temperature). Latent heat is usually defined as the amount of heat required for a substance to undergo a phase transition without a change in temperature. However, when the cured body of the present application exhibits the latent heat, it does not necessarily have to cause a state change as a whole. The latent heat of the cured body of the present application may occur in the process of changing the state of at least a part of the cured body or a component included in the cured body.

In the present application, that a cured material exhibits latent heat in a predetermined temperature range means that the cured material exhibits an endothermic peak in a predetermined temperature range in a Differential Scanning Calorimeter (DSC) analysis conducted in the manner described in Examples to be described later. The process in which the hardened material of the present application exhibits the latent heat is an isothermal process. Therefore, the hardened body can be applied to a product that generates heat to control the heat while maintaining a uniform temperature of the product, and the effect of abnormal heat generation, explosion, and/or ignition generated in one product on other adjacent products can be minimized or avoided.

The hardened body, for example, may exhibit a latent heat within the range of 20 to 200 J / g. In another example, the latent heat is 25 J/g or more, 30 J/g or more, 35 J/g or more, 40 J/g or more, 45 J/g or more, 50 J/g or more, 55 J/g or more, 60 J /g or more, 65 J/g or more, 70 J/g or more, 75 J/g or more, 80 J/g or more, 85 J/g or more, or 90 J/g or more, or 195 J/g or less, 190 J/g or less g or less, 185 J/g or less, 180 J/g or less, 175 J/g or less, 170 J/g or less, 165 J/g or less, 160 J/g or less, 155 J/g or less, 150 J/g or less , 145 J/g or less, 140 J/g or less, 135 J/g or less, 130 J/g or less, 125 J/g or less, 120 J/g or less, 115 J/g or less, 110 J/g or less, 105 J/g or less, 100 J/g or less, 95 J/g or less, 90 J/g or less, 85 J/g or less, 80 J/g or less, 75 J/g or less, 70 J/g or less, 65 J/g or less g or less, 60 J/g or less, 55 J/g or less, 50 J/g or less, 45 J/g or less, or 40 J/g or less.

This latent heat is an integral value of the endothermic peaks found in the DSC analysis of the cured product, and when a plurality of endothermic peaks are observed, it is an integral value for all the endothermic peaks.

The latent heat temperature at which the cured body exhibits the latent heat may be in the range of, for example, 0°C to 60°C. The latent heat temperature is the temperature at the apex of the endothermic peak observed in the DSC analysis. For example, when two or more endothermic peaks exist, the temperature of the apex of the main peak (the peak with the largest integral value) can be defined as the latent heat temperature. In another example, the latent heat temperature is 5 ° C or higher, 10 ° C or higher, 15 ° C or higher, 20 ° C or higher, 25 ° C or higher, 30 ° C or higher or 35 ° C or higher, or 55 ° C or lower, 50 ° C or lower, 45 ° C or lower or 40 ° C. It may be less or less.

The hardened body exhibiting the latent heat characteristics can be applied to various heat-generating products so that the products can be operated in a stable and uniform temperature range. In addition, the cured body can be applied to a product including a plurality of heat generating elements arranged relatively adjacently to maintain a uniform temperature of the entire product, and abnormal heat generation, ignition and/or explosion in any one element can be prevented. The influence on other elements can be minimized or prevented. In particular, the hardened body exhibiting the latent heat characteristic is applied to a product (eg, a secondary battery cell or a battery module or battery pack including a plurality of them) that needs to be maintained at a driving temperature within a range of about 15° C. to 60° C. You can control the heat with

The cured body of the present application can stably maintain the above latent heat characteristics for a long period of time. In one example, the curable composition may include a so-called phase change material (PCM) so that the cured material exhibits the latent heat characteristics. As the phase change material, a material that absorbs heat while undergoing a phase transition from a solid to a liquid may be used. Since such a material is converted to a liquid phase while exhibiting latent heat, it can be lost from the cured body. Therefore, in this case, the latent heat characteristics may be lost over time. In the present application, even after the phase change material in the cured body is transferred to the liquid phase through the selection of curable resin components forming the cured body, control of the degree of crosslinking, control of the type and ratio of the phase change material, and/or control of the manufacturing method of the curable composition, the cured body is not lost within, and therefore, the latent heat characteristics as described above can be stably maintained for a long period of time.

For example, the cured body of the present application may satisfy condition 1 below.

[Condition 1]

ΔW = 100 × (W _f - W _i )/W _i ≤ 3%

In condition 1, ΔW is the weight change rate (unit %) of the cured product, Wf is the weight of the cured product measured after maintaining the cured product at 80° C. for 24 hours, and Wi is the weight before maintaining the cured product at 80° C. for 24 hours. is the weight of the cured body.

A specific method for measuring condition 1 is described in the Examples section. In addition, the units of the weights (W _f and W _i ) in Condition 1 are not limited as long as the same units are applied.

The weight change rate (ΔW) is, in another example, 2.5% or less, 2% or less, 1.5% or less, 1% or less, 0.9% or less, 0.8% or less, 0.7% or less, 0.6% or less, 0.5% or less, 0.4% It may be about 0.3% or less or 0.2% or less. Since the weight change rate (ΔW) means that the smaller the value, the more stable the phase change material is maintained in the cured body, the lower limit is not particularly limited. The weight change rate (ΔW) may be 0% or more in one example.

In the present application, the latent heat characteristics or weight change characteristics can be achieved without applying a so-called composite material as a phase change material. A phase change material exhibits an endothermic property capable of controlling heat, but generally has poor thermal conductivity. Therefore, it is not easy to transfer the heat to be treated to the phase change material. For this purpose, a composite material in which a material having high thermal conductivity such as graphite or carbon fiber is combined with a phase change material is known. These materials can solve the problem of low thermal conductivity, which is a disadvantage of phase change materials, to some extent, but are disadvantageous in terms of weight reduction because they increase the density or specific gravity of the material. However, in the present application, the selection of the curable resin component forming the curable body, the control of the degree of crosslinking, the control of the type and ratio of the phase change material and / or the control of the manufacturing method of the curable composition without using the complexed phase change material , It is possible to solve the problem of thermal control efficiency deterioration due to low thermal conductivity, which is a disadvantage of phase change materials, and accordingly, it is possible to provide a lightweight material.

In one example, the cured body may have a density in the range of 0.7 to 1.5 g/ml. In another example, the density is 0.75 g/ml or more, 0.8 g/ml or more, 0.85 g/ml or more, 0.9 g/ml or more, 0.95 g/ml or more, 1 g/ml or more, 1.05 g/ml or more, 1.1 g /ml or more or 1.15 g/ml or more, 1.45 g/ml or less, 1.4 g/ml or less, 1.35 g/ml or less, 1.3 g/ml or less, 1.25 g/ml or less, 1.2 g/ml or less, 1.15 g/ml or less ml or less, 1.1 g/ml or less, 1.05 g/ml or less, 1 g/ml or less, or 0.95 g/ml or less. Under this density, it is possible to provide a lightweight material.

The hardened body of the present application may exhibit Shore OO hardness in the range of 20 to 90 or Shore A hardness in the range of 10 to 60. The Shore OO hardness may be 25 or more, 30 or more, 35 or more, 40 or more, 45 or more, or 50 or more, or 85 or less, 80 or less, 75 or less, 70 or less, 65 or less, or 60 or less in another example, the Shore A hardness may be 15 or more, 20 or more, 25 or more, 30 or more, or 35 or more, or 55 or less, 50 or less, or 45 or less in another example.

The hardness of the cured body may be determined in relation to the molecular weight and degree of crosslinking of the curable resin component. In the present application, the molecular weight of the curable resin component forming the curable body and the degree of crosslinking of the resin component are controlled to exhibit hardness within the above range. , can provide a network capable of stably maintaining the phase change material. In addition, the hardness within the above range enables the cured material to stably fill a space having a complex shape, and also improves vibration resistance and impact resistance.

The curable composition of the present application may include a curable resin component. The scope of the term curable resin component includes a component capable of forming a resin component after curing reaction as well as a case where it is a so-called resin component itself. Accordingly, the curable resin component may be a monomolecular, oligomeric or polymeric compound.

In the present application, as the curable resin component, a weight average molecular weight (Mw, Weight Average Molecular Weight) may be 9000 g/mol or more. In another example, the weight average molecular weight is 10000 g/mol or more, 15000 g/mol or more, 20000 g/mol or more, or 25000 g/mol or more, or 100000 g/mol or less, 90000 g/mol or less, or 80000 g/mol or less. , 70000 g/mol or less, 60000 g/mol or less, 50000 g/mol or less, 40000 g/mol or less, or 30000 g/mol or less. The curable resin component having such molecular weight characteristics may form a network of cured bodies in which the phase change material can be stably maintained. In particular, as a resin component having the above molecular weight characteristics, a silicone resin component can be effectively applied.

There is no particular limitation on the kind of curable resin component. In one example, the curable resin component may include a polyurethane component, a silicone resin component, an acrylic resin component, or an epoxy resin component. The polyurethane component, silicone resin component, acrylic resin component or epoxy resin component is polyurethane, silicone resin, acrylic resin or epoxy resin, or through a curing reaction to form the polyurethane, silicone resin, acrylic resin or epoxy resin may be an ingredient. There is no particular limitation on the specific type of curable resin component that can be applied, and those exhibiting molecular weight characteristics and/or hardness characteristics as described above are selected and used from known polyurethane components, silicone resin components, acrylic resin components, or epoxy resin components. And, by controlling the degree of crosslinking of these resin components, the hardness of the final cured product may be controlled.

For example, when the curable resin component is a silicone resin component, the component is an addition curable silicone resin component comprising (1) a polyorganosiloxane containing two or more alkenyl groups in a molecule and (2) two or more alkenyl groups in a molecule. polyorganosiloxanes containing one or more silicon-bonded hydrogen atoms. The compound may form a cured product by an addition reaction in the presence of a catalyst such as a platinum catalyst.

Said (1) polyorganosiloxane contains at least 2 alkenyl groups. At this time, specific examples of the alkenyl group include a vinyl group, an allyl group, a butenyl group, a pentenyl group, a hexenyl group, or a heptenyl group, among which a vinyl group is usually applied, but is not limited thereto. In the above (1) polyorganosiloxane, the bonding position of the alkenyl group described above is not particularly limited. For example, the alkenyl group may be bonded to the end of the molecular chain and/or to the side chain of the molecular chain. Further, in the (1) polyorganosiloxane, examples of substituents that may be included in addition to the aforementioned alkenyl include an alkyl group such as a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, or a heptyl group; Aryl groups, such as a phenyl group, a tolyl group, a xylyl group, or a naphthyl group; Aralkyl groups, such as a benzyl group or a phenentyl group; and a halogen-substituted alkyl group such as a chloromethyl group, 3-chloropropyl group, or 3,3,3-trifluoropropyl group, among which a methyl group or a phenyl group is usually applied, but is not limited thereto.

The molecular structure of the above (1) polyorganosiloxane is not particularly limited, and may have any shape, such as, for example, linear, branched, cyclic, network, or partially branched linear. Among the above molecular structures, those having a linear molecular structure are usually applied, but are not limited thereto.

More specific examples of the above (1) polyorganosiloxane include a dimethylsiloxane-methylvinylsiloxane copolymer blocking trimethylsiloxane groups at both molecular chain ends, a methylvinylpolysiloxane blocking trimethylsiloxane groups at both molecular chain ends, and a trimethylsiloxane group at both molecular chain ends. Blocking dimethylsiloxane-methylvinylsiloxane-methylphenylsiloxane copolymer, blocking dimethylvinylsiloxane groups at both ends of the molecular chain Dimethylpolysiloxane blocking dimethylvinylsiloxane groups at both ends of the molecular chain, blocking dimethylvinylsiloxane groups at both ends of the molecular chain dimethylsiloxane- Methylvinylsiloxane copolymer, dimethylsiloxane-methylvinylsiloxane-methylphenylsiloxane copolymer with both ends of the molecular chain capped with dimethylvinylsiloxane groups, composed of siloxane units represented by R ¹ ₂ SiO _2/2 and R ¹ ₂ R ² SiO _1/2 A polyorganosiloxane copolymer comprising a siloxane unit represented by SiO _4/2 and a siloxane unit represented by R ¹ ₂ R ² SiO _1/2 and a siloxane unit represented by SiO _4/2 A polyorganosiloxane copolymer comprising a siloxane unit represented by R ¹ R ² SiO _2/2 and a siloxane unit represented by R ¹ SiO _3/2 or a siloxane unit represented by R ² SiO _3/2 ganosiloxane copolymers and mixtures of two or more of the above, but are not limited thereto. In the above, R ¹ is a hydrocarbon group other than an alkenyl group, specifically an alkyl group such as a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group or a heptyl group; Aryl groups, such as a phenyl group, a tolyl group, a xylyl group, or a naphthyl group; Aralkyl groups, such as a benzyl group or a phenentyl group; It may be a halogen-substituted alkyl group such as a chloromethyl group, a 3-chloropropyl group, or a 3,3,3-trifluoropropyl group. In addition, in the above, R ² is an alkenyl group, and specifically may be a vinyl group, an allyl group, a butenyl group, a pentenyl group, a hexenyl group, or a heptenyl group.

In the addition-curable silicone composition, (2) the polyorganosiloxane may serve to cross-link the (1) polyorganosiloxane. In the above (2) polyorganosiloxane, the bonding position of the hydrogen atom is not particularly limited, and may be bonded to the terminal and/or side chain of the molecular chain, for example. In addition, in the (2) polyorganosiloxane, the type of substituent that may be included in addition to the silicon-bonded hydrogen atom is not particularly limited, for example, as mentioned in (1) polyorganosiloxane, an alkyl group, an aryl group, an aralkyl group or a halogen-substituted alkyl group, among which a methyl group or a phenyl group is usually applied, but is not limited thereto.

The molecular structure of the above (2) polyorganosiloxane is not particularly limited, and may have any shape, such as, for example, linear, branched, cyclic, network, or partially branched linear. Of the above molecular structures, those having a linear molecular structure are usually applied, but are not limited thereto.

More specific examples of the above (2) polyorganosiloxane include methylhydrogenpolysiloxane blocking trimethylsiloxane groups at both ends of the molecular chain, dimethylsiloxane-methylhydrogen copolymer blocking trimethylsiloxane groups at both molecular ends, and trimethylsiloxane at both molecular chain ends. Acid group blocking dimethylsiloxane-methylhydrogensiloxane-methylphenylsiloxane copolymer, molecular chain terminals dimethylhydrogensiloxane group blocking dimethylpolysiloxane, molecular chain terminals dimethylhydrogensiloxane blockade dimethylsiloxane-methylphenylsiloxane copolymer, molecular chain terminals Methylphenylpolysiloxane capped with dimethylhydrogensiloxane groups, polyorgano comprising siloxane units represented by R ¹ ₃ SiO _1/2 and siloxane units represented by R ¹ ₂ HSiO _1/2 and siloxane units represented by SiO _4/2 Siloxane copolymer, polyorganosiloxane copolymer comprising a siloxane unit represented by R ¹ ₂ HSiO _1/2 and a siloxane unit represented by SiO _4/2 , a siloxane unit represented by R ¹ HSiO _2/2 and R ¹ polyorganosiloxane copolymers including siloxane units represented by SiO _3/2 or siloxane units represented by HSiO _3/2 and mixtures of two or more of the above, but are not limited thereto. In the above, R ¹ is a hydrocarbon group other than an alkenyl group, specifically an alkyl group such as a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, or a heptyl group; Aryl groups, such as a phenyl group, a tolyl group, a xylyl group, or a naphthyl group; Aralkyl groups, such as a benzyl group or a phenentyl group; It may be a halogen-substituted alkyl group such as a chloromethyl group, a 3-chloropropyl group, or a 3,3,3-trifluoropropyl group.

The content of (2) polyorganosiloxane is not particularly limited as long as it is included to the extent that appropriate curing can be achieved. For example, the polyorganosiloxane (2) may contain 0.5 to 10 silicon-bonded hydrogen atoms per alkenyl group included in the polyorganosiloxane (1). Within this range, curing can be sufficiently advanced and heat resistance can be ensured.

The addition-curable silicone resin component may further include platinum or a platinum compound as a catalyst for curing. The specific kind of such platinum or platinum compound is not particularly limited. The ratio of the catalyst may also be adjusted to a level at which proper curing can be achieved.

In another example, the silicone resin component is a condensation-curable silicone resin component, for example (a) an alkoxy group-containing siloxane polymer; and (b) a hydroxyl group-containing siloxane polymer.

The (a) siloxane polymer may be, for example, a compound represented by Formula 1 below.

[Formula 1]

R ¹ _a R ² _b SiO _c (OR ³ ) _d

In Formula 1, R ¹ and R ² each independently represent a hydrogen atom or a substituted or unsubstituted monovalent hydrocarbon group, R ³ represents an alkyl group, and when a plurality of R ¹ , R ² and R ³ are present, respectively, may be the same as or different from each other, a and b each independently represent a number greater than or equal to 0 and less than 1, a+b represents a number greater than 0 and less than 2, and c represents a number greater than 0 and less than 2 , d represents a number greater than 0 and less than 4, and a+b+c×2+d is 4.

In the definition of Formula 1, the monovalent hydrocarbon may be, for example, an alkyl group having 1 to 8 carbon atoms, a phenyl group, a benzyl group, or a tolyl group, and in this case, the alkyl group having 1 to 8 carbon atoms includes a methyl group, an ethyl group, a propyl group, It may be an isopropyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group or an octyl group. In the definition of Formula 1, the monovalent hydrocarbon group may be substituted with a known substituent such as, for example, a halogen, an amino group, a mercapto group, an isocyanate group, a glycidyl group, a glycidoxy group, or a ureido group.

In the definition of Formula 1, examples of the alkyl group of R ³ include a methyl group, an ethyl group, a propyl group, an isopropyl group, or a butyl group. Among the alkyl groups, a methyl group or an ethyl group is usually applied, but is not limited thereto.

Among the polymers of Formula 1, branched or tertiary crosslinked siloxane polymers may be used. Further, in the (a) siloxane polymer, a hydroxyl group may remain within a range that does not impair the purpose, specifically within a range that does not inhibit the dealcoholization reaction.

The (a) siloxane polymer can be produced, for example, by hydrolyzing and condensing a polyfunctional alkoxysilane or a polyfunctional chlorosilane. An average person skilled in this field can easily select an appropriate polyfunctional alkoxysilane or chlorosilane according to the desired (a) siloxane polymer, and can also easily control the conditions of hydrolysis and condensation reactions using the same. On the other hand, in the case of producing the siloxane polymer (a), an appropriate monofunctional alkoxy silane may be used in combination depending on the purpose.

As the siloxane polymer (a), commercially available organosiloxanes such as X40-9220 or X40-9225 from Shin-Etsu Silicone Co., XR31-B1410, XR31-B0270 or XR31-B2733 from GE Toray Silicone Co., Ltd. polymers can be used.

As the hydroxyl group-containing siloxane polymer (b) included in the condensation-curable silicone composition, for example, a compound represented by the following formula (2) can be used.

[Formula 2]

In Formula 2, R ₄ and R ₅ each independently represent a hydrogen atom or a substituted or unsubstituted monovalent hydrocarbon group, and when a plurality of R ₄ and R ₅ are present, they may be identical to or different from each other. And, n represents an integer from 5 to 2,000.

In the definition of Formula 2, specific types of monovalent hydrocarbon groups include, for example, the same hydrocarbon groups as in the case of Formula 1 above.

The (b) siloxane polymer can be produced by, for example, hydrolysis and condensation of dialkoxysilane and/or dichlorosilane. An average person skilled in the art can easily select an appropriate dialkoxy silane or dichloro silane depending on the desired (b) siloxane polymer, and can also easily control the conditions for hydrolysis and condensation reactions using them. As the above (b) siloxane polymer, for example, commercially available bifunctional organosiloxane polymers such as XC96-723, YF-3800, and YF-3804 manufactured by GE Toray Silicone Co., Ltd. can be used.

The addition-curing or condensation-curing silicone composition described above is an example of the silicone resin component applied in the present application.

In another example, if the curable resin component is a polyurethane component, the component may include at least polyol and polyisocyanate. In the above, polyol is a compound containing at least two hydroxyl groups, and polyisocyanate is a compound containing at least two isocyanate groups. These compounds may be monomolecular, oligomeric or macromolecular compounds, respectively.

The type of polyol that can be applied is not particularly limited, and, for example, known polyether polyols or polyester polyols can be applied. In the above, the polyether polyol is a polyalkylene glycol having 1 to 20, 1 to 16, 1 to 12, 1 to 8 or 1 to 4 carbon atoms in the alkylene glycol portion such as polypropylene glycol or polyethylene glycol, or ethylene oxide Seed/propylene oxide copolymer-based polyols, poly(tetramethylene glycol) (PTME), poly(hexamethylene ether glycol) (PHMG), and the like are known. In addition, the polyester polyol is a polyol synthesized from a dibasic acid and glycol, and a polyester polyol or a polycaprolactone polyol (obtained from ring-opening polymerization of a cyclic lactone) containing the dibasic acid unit and a glycol unit, and the like It is known. In addition to the above polyols, hydrocarbon-based polyols such as carbonate-based polyols, vegetable polyol castor oil, hydroxyl-terminated polybutadiene (HTPB) and hydroxyl-terminated polyisobutylene (HTTPB) are also known.

In the present application, an appropriate kind may be selected and used among the above known polyols.

As the polyisocyanate, an appropriate type selected from well-known aromatic or aliphatic polyisocyanate compounds may be used.

The curable composition contains the curable resin component in an amount of 50 wt% or more, 55 wt% or more, 60 wt% or more, 65 wt% or more, 70 wt% or more, 75 wt% or more, or 80 wt% or more based on the total weight of the curable composition. It may contain more than 100% by weight, 95% by weight or less, 90% by weight or less, 85% by weight or less, 80% by weight or less, 75% by weight or less, 70% by weight or less, or 65% by weight or less. The content is based on the total weight of the curable composition, provided that, when the curable composition includes a filler and/or a solvent, it is a ratio based on the total weight of the curable composition excluding the filler and the solvent.

The curable composition may include a so-called phase change material (PCM) in order to secure the aforementioned latent heat characteristics. A phase change material, as is well known, is a material that absorbs heat or generates heat in a phase transition process. The phase transition process is an isothermal process.

As the phase change material, in one example, a so-called core-shell material may be used. The core cell type may include a material that absorbs heat or generates heat during the phase transition process at least in the core portion, and cells made of a predetermined material exist around the core cell type. By applying this type of phase change material, a curable composition of a desired type can be efficiently achieved.

The phase change in which the core of the phase change material or the core cell type phase change material emits heat or exotherms may be a phase transition from solid to solid, from solid to liquid, from solid to gas, or from liquid to gas. The above-described phase transition reaction (solid → solid, solid → liquid, solid → gas, liquid → gas) may be an endothermic reaction. In terms of efficiency, materials that undergo phase transition from solid to liquid are advantageous, but since such materials become liquid after phase transition, it is difficult to maintain them in a hardened body. However, the hardened body of the present application exhibits the above-mentioned weight change rate, and therefore can apply a material that undergoes phase transition from solid to liquid. Accordingly, the phase change material applied in the present application may be a material in which a phase transition occurs between a solid phase and a liquid phase, and the phase transition reaction from the solid phase to the liquid phase may be an endothermic reaction.

The phase change material applied in the present application or the core of the phase change material in the form of a core cell may be a material having a melting point in the range of 5°C to 100°C. In another example, the melting point of the phase change material is 10 ° C, 15 ° C, 20 ° C, 25 ° C or more, 30 ° C or more, 35 ° C or more, 40 ° C or more, 45 ° C or more or 50 ° C or more, or 95 ° C or less, 90 ° C or less. .

A phase change material exhibiting a latent heat within the range of 50 to 400 J/g at a temperature within the range of 5°C to 100°C may be used as the core of the phase change material or core cell type phase change material. That is, the core of the phase change material may have a latent heat temperature in the range of 5°C to 100°C. At this time, the definition of the latent heat temperature is the same as that of the hardened body. The temperature at which the phase change material exhibits latent heat is, in another example, 10 ° C or more, 15 ° C or more, 20 ° C or more, 25 ° C or more, 30 ° C or more, 35 ° C or more, 40 ° C or more, 45 ° C or more, or 50 ° C or more, 95°C or less, 90°C or less, 85°C or less, 80°C or less, 75°C or less, 70°C or less, 65°C or less, 60°C or less, 55°C or less, 50°C or less, or 45°C or less.

In addition, the latent heat of the phase change material at the above temperature is, in another example, 60 J/g or more, 70 J/g or more, 80 J/g or more, 90 J/g or more, 100 J/g or more, or 105 J/g or more, or , 390 J/g or less, 380 J/g or less, 370 J/g or less, 360 J/g or less, 350 J/g or less, 340 J/g or less, 330 J/g or less, 320 J/g or less, 310 J/g or less, 300 J/g or less, 290 J/g or less, 280 J/g or less, 270 J/g or less, 260 J/g or less, 250 J/g or less, 240 J/g or less, 230 J/g or less g or less, 220 J/g or less, 210 J/g or less, 200 J/g or less, 190 J/g or less, 180 J/g or less, 170 J/g or less, 160 J/g or less, 150 J/g or less , 140 J/g or less, 130 J/g or less, or 120 J/g or less.

Through the application of the phase change material or the phase change material including the core as above, it is possible to form a desired cured body.

As the core of the phase change material or the core cell type phase change material, any known material may be applied as long as it exhibits the above-described characteristics. An inorganic material, an organic material, or a eutectic material is known as a phase change material or a core of a core cell type phase change material. Among these materials, as a material having the above-described latent heat characteristics, an organic phase change material may be used.

As the organic phase change material, fatty acid, alcohol (polyalcohol), ketone, D-lactic acid, or paraffin-based material is known, and in this application, one of the above materials Alternatively, a mixture of two or more may be used.

Examples of the fatty acid include formic acid, n-octanoic acid, lauric acid or palmitic acid, stearic acid, and the like. may be exemplified, and as an alcohol-based phase change material, glycerin, polyethylene glycol (PEG), xylitol, or erythritol may be exemplified, and as a ketone-based phase change material, 2 -Pentadecanone (2-pentadecanone) or 4-heptadecanone (4-heptadekanone) and the like can be exemplified.

In an appropriate example, a paraffin-based material may be used as a core of a phase change material or a core cell type phase change material. As the paraffinic phase change material, n-heptadecane, n-octadecane, n-nonadecane, n-Eicosane, n-henney n-henicosane, n-docosane, n-tricosane, n-pentacosane, n-hexacosane, n-hep n-heptacosane, n-octacosane, n-nonacosane, n-triacontane, n-hentriacontane ), n-dotriacontane, n-triatriacontane or other higher order paraffins (Paraffin C ₁₆ ~ C ₁₈ , Paraffin C ₁₃ ~ C ₂₄ , RT 35 HC, Paraffin C ₁₆ ~ C ₂₈ , Paraffin C ₂₀ ~ C ₃₃ , Paraffin C ₂₂ ~ C ₄₅ , Paraffin C ₂₂ ~ C ₅₀ , Paraffin natural wax 811, Paraffin natural wax 106, etc.) are known.

In the present application, an appropriate type may be selected and used among the known paraffinic materials.

In order to achieve appropriate effects, in the present application, paraffin having a melting point in the above range and having 5 or more carbon atoms may be used as a core of the phase change material or core cell type phase change material. The carbon number of the paraffin may be within the range of 5 to 40 or within the range of 16 to 25 in another example. Such paraffin may be an alkane having the above number of carbon atoms.

When the phase change material is in the form of a core cell, the cell of the phase change material includes fatty acid; acrylic polymer; acrylic polymer and n-hexadecane; acrylic polymer and polyethylene glycol; or polyvinyl alcohol and tetradecane.

In the above, as the fatty acid, for example, a compound represented by Chemical Formula 3 may be used.

[Formula 3]

In Formula 3, n is a number within the range of about 10 to 30.

In addition, as the acrylic polymer in the above, a material known to have a high glass transition temperature (Tg) may be used, for example, PMMA (poly(methylmethacrylate)), polyoctadecyl methacrylate and/or polyacrylic acid, etc. this may apply.

The phase change material including the cell of these materials can be combined with the material of the core to allow the cured product to exhibit appropriate latent heat at an appropriate temperature, and to prevent loss of the phase change material while maintaining the desired performance of the cured product stably for a long period of time. can

The method of manufacturing the phase change material including the cell as described above is not particularly limited, and, for example, by applying a known physical method, chemical method, or a combination of the physical method and the chemical method (physical/chemical method) can be manufactured

As the physical method, a so-called spray drying method or a solvent volatilization method is known, and as a chemical method, in-situ polymerization, interfacial polymerization, suspension polymerization, or emulsion polymerization is known. In addition, a method using a sol-gel process in a physical/chemical manner and a coacervation method in which two phases are separated using a hydrophilic colloidal solution are known.

In addition, a commercially available material may be used as the phase change material in the form of a core cell as described above.

As the phase change material in the form of a core cell, a material having an average particle diameter of 500 μm or less may be used. The above average particle diameter is the D50 particle diameter measured by the method described in the Examples described later. In another example, the average particle diameter of the phase change material may be 450 μm or less, 400 μm or less, 350 μm or less, 300 μm or less, 250 μm or less, 200 μm or less, or 150 μm or less, or 50 μm or more, 70 μm or more, 90 μm or more, or 110 μm or more.

A phase change material having an average particle diameter within this range is advantageous for forming a cured body exhibiting the effect intended in the present application.

The phase change material may be included in the range of about 20 to 100 parts by weight based on 100 parts by weight of the curable resin component in the curable composition, and a desired effect can be efficiently secured under this ratio. In another example, the ratio of the phase change material is 21 parts by weight or more, 22 parts by weight or more, 23 parts by weight or more, 24 parts by weight or more, or 25 parts by weight or more, 95 parts by weight or less, 90 parts by weight or more, based on 100 parts by weight of the curable resin component. 85 parts by weight or less, 80 parts by weight or less, 75 parts by weight or less, 74 parts by weight or less, 73 parts by weight or less, 72 parts by weight or less, 71 parts by weight or less, 70 parts by weight or less, 69 parts by weight or less, 68 parts by weight or less 67 parts by weight or less, 66 parts by weight or less, 65 parts by weight or less, 64 parts by weight or less, 63 parts by weight or less, 62 parts by weight or less, 61 parts by weight or less, or 60 parts by weight or less.

The curable composition may contain a filler such as a thermally conductive filler as an optional additional component. These fillers can compensate for the low thermal conductivity of the phase change material.

The heat conductive filler that can be applied is not particularly limited, and examples thereof include aluminum hydroxide (Al(OH) ₃ ), magnesium hydroxide (Mg(OH) ₂ ), calcium hydroxide (Ca(OH) ₂ ), and boehmite (AlOOH). ), hydromagnesite, magnesia, alumina, aluminum nitride (AlN), boron nitride (BN), silicon nitride (Si ₃ N ₄ , silicon nitride), silicon carbide (SiC), zinc oxide (ZnO) Alternatively, an inorganic filler such as beryllium oxide (BeO) may be exemplified, but is not limited thereto. One type or two or more types may be selected from the above fillers. In the case of forming a low-density cured body, a filler having a small specific gravity (eg, aluminum hydroxide, etc.) may be selected from among the filler components.

In the above, the shape of the filler is not particularly limited, and for example, spherical, needle-shaped, plate-shaped and other amorphous fillers may be used.

In one example, a filler having an average particle diameter in the range of 10 μm to 200 μm may be used as the filler. The above average particle diameter is the D50 particle diameter measured by the method described in the Examples described later. The desired effect can be more efficiently secured through the application of a filler having such a particle size.

In another example, the particle diameter of the filler is 15 μm or more, 20 μm or more, 25 μm or more, 30 μm or more, 35 μm or more, or 40 μm or more, or 180 μm or less, 160 μm or less, 140 μm or less, 120 μm or less, 100 μm or less It may be about μm or less, 80 μm or less, 60 μm or less, or 50 μm or less.

The content of the thermally conductive filler in the curable composition is adjusted according to the purpose. For example, in the curable composition, the thermally conductive filler may be included in an amount of about 200 parts by weight or less based on 100 parts by weight of the curable resin component. In another example, the ratio is 195 parts by weight or less, 190 parts by weight or less, 185 parts by weight or less, 180 parts by weight or less, 175 parts by weight or less, 170 parts by weight or less, 165 parts by weight or less, 160 parts by weight or less, 155 parts by weight or less. , 150 parts by weight or less, 145 parts by weight or less, 140 parts by weight or less, 135 parts by weight or less, 130 parts by weight or less, 125 parts by weight or less, 120 parts by weight or less, 115 parts by weight or less, 110 parts by weight or less, 105 parts by weight or less , 100 parts by weight or less, 95 parts by weight or less, 90 parts by weight or less, 85 parts by weight or less, 80 parts by weight or less, 75 parts by weight or less, 70 parts by weight or less, 65 parts by weight or less, 60 parts by weight or less, 55 parts by weight or less , 50 parts by weight or less, 45 parts by weight or less, or 40 parts by weight or less, or 10 parts by weight or more, 15 parts by weight or more, 20 parts by weight or more, 25 parts by weight or more, 30 parts by weight or more, 35 parts by weight or more, or 40 parts by weight It may be more or less.

The curable composition may further include a hollow filler as an optional additional component in view of weight reduction.

Through the application of the hollow filler can contribute to weight reduction.

For example, the filler may have a D50 particle diameter (average particle diameter) within a range of 10 μm to 100 μm. In another example, the D50 particle diameter is 12 μm or more, 14 μm or more, 16 μm or more, 18 μm or more, 20 μm or more, 22 μm or more, 24 μm or more, 26 μm or more, 28 μm or more, 30 μm or more, 32 μm or more , 34 μm or more, 36 μm or more, 38 μm or more, 40 μm or more, 42 μm or more, 44 μm or more, 46 μm or more, 48 μm or more, 50 μm or more, 52 μm or more, 54 μm or more, 56 μm or more, or 58 98 μm or less, 96 μm or less, 94 μm or less, 92 μm or less, 90 μm or less, 88 μm or less, 86 μm or less, 84 μm or less, 82 μm or less, 80 μm or less, 78 μm or less, 76 μm or less or less, 74 μm or less, 72 μm or less, 70 μm or less, 68 μm or less, 66 μm or less, 64 μm or less, 62 μm or less, or 60 μm or less.

The hollow filler may have a density in the range of about 0.05 to 1 g/ml. In another example, the density is 0.01 g/ml or more, 0.15 g/ml or more, 0.2 g/ml or more, 0.25 g/ml or more, 0.3 g/ml or more, 0.35 g/ml or more, 0.4 g/ml or more, or 0.45 g/ml or more. g/ml or more, 0.5 g/ml or more, 0.55 g/ml or more, or 0.6 g/ml or more, or 0.95 g/ml or less, 0.9 g/ml or less, 0.85 g/ml or less, 0.8 g/ml or less, 0.75 g /ml or less, 0.7 g/ml or less, 0.65 g/ml or less, 0.6 g/ml or less, 0.55 g/ml or less, 0.5 g/ml or less, 0.45 g/ml or less, 0.4 g/ml or less, 0.35 g/ml It may be about 0.3 g/ml or less, 0.25 g/ml or less, 0.2 g/ml or less, or 0.15 g/ml or less.

As the hollow filler, various types may be used without particular limitation as long as they have the above particle size and/or density and can be uniformly mixed with the curable polyorganosiloxane component.

For example, as the hollow filler, a known organic filler, inorganic filler, or organic/inorganic mixed filler can be used. Even when the hollow filler is applied, organic particles whose shells are made of organic materials, inorganic particles made of inorganic materials, and/or organic/inorganic particles made of organic/inorganic materials may be used. Examples of such particles include acrylic particles such as poly(methyl methacrylate) (PMMA), epoxy particles, nylon particles, styrene particles, and/or copolymer particles of styrene/vinyl monomers, silica particles, alumina particles, indium oxide particles, oxide particles, and the like. Inorganic particles such as tin particles, zirconium oxide particles, zinc oxide particles, and/or titania particles may be exemplified, but are not limited thereto.

In one example, the hollow filler includes particles in which the shell portion is made of a soda-lime material (soda-lime filler), and particles in which the cell portion is made of a soda-lime borosilicate material ( soda lime borosilicate filler), cenosphere filler or other silica particles may be applied.

When the hollow filler is included, there is no particular limitation on the ratio, and it may be selected in an appropriate ratio within a range in which the desired weight reduction is possible without impairing the physical properties of the cured body.

The curable composition may contain other necessary components in addition to the above components. For example, the curable composition may further include additional additives such as a catalyst, a pigment or dye, a dispersant, a thixotropic agent, a flame retardant, and the like, in addition to the above components, if necessary.

Such a curable composition may be a solvent-type composition, an aqueous composition, or a non-solvent-type composition, and may be a solvent-free composition as appropriate.

As described above, the curable composition may be a one-component composition or a two-component composition, and in some cases may be a main agent or a curing agent part of a two-component composition, or a mixture of the main agent and a curing agent part.

In addition, when the curable composition is a two-component composition, there is no particular limitation on the ratio of components other than the curable resin component in the main and curing agent parts. For example, the phase change material and/or filler may be included in both the main agent and the curing agent part, or may be separately included in the main subject and the curing agent part.

The curable composition of the present application is suitably used for various purposes, and in particular, it can be applied to a heating product and used as a material for controlling the heat of the product.

In one example, a method for preparing the curable composition may be selected to satisfy the aforementioned latent heat characteristics, weight change rate, density and/or hardness characteristics.

For example, the curable composition may be prepared by mixing the phase change material and a curable resin component in a state in which the phase change material is melted. Through these steps, a desired curable composition can be more effectively provided.

Therefore, the method for preparing the curable composition may include mixing the molten phase change material and the curable resin component, and specifically, the first step of melting the phase change material and mixing the molten phase change material and the curable resin component. steps may be included.

A method of melting the phase change material in the above is not particularly limited, and, for example, it may be melted by maintaining the phase change material at a temperature equal to or higher than the melting point of the phase change material. In one example, the maintenance temperature of the phase change material may be 10 °C to 100 °C higher than the melting point of the phase change material. In another example, the temperature is 15 ° C or more, 20 ° C or more, 25 ° C or more or 30 ° C or more higher than the melting point of the phase change material, or 95 ° C or less, 90 ° C or less, 85 ° C or less, 80 ° C or less compared to the melting point of the phase change material. °C or less, 75 °C or less, 70 °C or less, 65 °C or less, 60 °C or less, 55 °C or less, 50 °C or less, 45 °C or less, 40 °C or less, 35 °C or less or 30 °C or less.

A curable curable composition having desired properties can be efficiently prepared by preparing a curable composition by mixing the phase change material melted in this temperature range and the curable resin component. Meanwhile, a temperature at the time of mixing the molten phase change material and the curable resin component may be a temperature within the same range as the temperature at which the phase change material is melted, or a temperature lower than that.

This application also relates to a cured product of the curable composition described above. A method of obtaining a cured body by curing the curable composition is not limited, and an appropriate curing method may be applied depending on the type of the curable composition. For example, in the case of an energy ray curing type, a method of irradiating the composition with energy rays such as ultraviolet rays, in the case of a moisture curing type, a method of maintaining the composition under appropriate moisture, in the case of a heat curing type, a method of applying appropriate heat to the composition, In the case of a room temperature curing type, a method of maintaining the composition at room temperature, a method of applying two or more types of curing methods in the case of a hybrid curing type, and the like may be used. As described above, in a suitable example, the curable composition may be curable at room temperature.

This application also relates to a product containing the composition or a cured product thereof. The curable composition or cured product thereof of the present application may be usefully applied as a material for controlling the heat of a heating component, a heating element, or a heating product. Accordingly, the product may include a heating component or a heating element or a heating product. The term heating component, element, or product means a part, element, or product that emits heat during use, and the type is not particularly limited. Representative heating parts, devices, or products include various electric/electronic products including battery cells, battery modules, or battery packs.

The product of the present application may include, for example, the curable composition (or the two-component composition) or a cured product thereof existing adjacent to the heating component, device, or product and the heating component. In this case, as described above, the heating part, element, or product may be a part, element, or product having an appropriate driving temperature within a range of about 15°C to 60°C. That is, the curable composition of the present application is useful for maintaining the operating temperature of the product uniformly within the above range by being disposed adjacent to a heating component, element, or product.

A specific method of configuring the product of the present application is not particularly limited, and if the curable composition or the two-component composition or the cured product of the present application is applied as a heat dissipation material, the product may be configured in various known ways.

In one example, the curable composition may be used as a potting material when constructing a battery module or battery pack. The potting material may be a material that contacts and covers at least some or all of the plurality of unit battery cells in the battery module or battery pack. The curable composition or cured product thereof of the present application, when applied as the potting material, can control heat generated from a battery cell of a battery module or pack, prevent chain ignition or explosion, and the module or pack Alternatively, the operating temperature of the battery cell may be maintained uniformly. In the present application, it is also possible to provide a curable composition having excellent potting efficiency by controlling viscosity or thixotropy to an appropriate level before curing and forming a stable potting structure without generating unnecessary bubbles after curing. In the present application, it is possible to provide a curable composition that exhibits a low density after curing and can provide a battery module or pack that is lightweight and has high output compared to the volume. In this application, it is possible to provide a curable composition excellent in required physical properties including insulation and the like.

In this case, as a battery-related technology, the curable composition may be applied as a heat dissipation material such as a battery module or a battery pack or a heat dissipation material of an on board charger (OBC) for a vehicle. Therefore, the present application may also relate to a battery module, battery pack, or on-board charger (OBC) including the curable composition or a cured product thereof as a heat dissipation material. The application position or application method of the curable composition or cured body in the battery module, battery pack or on-board charger is not particularly limited, and a known method may be applied. In addition, the curable composition of the present application is not limited to the above uses, and can be effectively applied to various uses requiring excellent heat dissipation properties, storage stability, and adhesive strength.

In another example related to the present application, the present application may relate to electronic equipment or devices having a cured body of the curable composition.

The type of electronic equipment or device is not particularly limited, and examples include audio video navigation (AVN) for vehicles, on board charger (OBC) modules for electric vehicles, LED modules or IC chips, and computers or mobile devices including the same. can

The hardened body of the curable composition may dissipate heat in the equipment or device, and may impart durability against impact, insulation, and the like.

The curable composition may be used as a battery potting material in one example.

This application also relates to a battery module to which the potting material is applied. Such a battery module can exhibit high output while being lightweight compared to the same volume, and heat generated from battery cells is appropriately controlled, and problems such as chain ignition do not occur.

The battery module, in one example a substrate; a plurality of battery cells disposed on the substrate; and the curable composition or a cured product thereof covering at least some or all of the plurality of battery cells.

In the above structure, the curable composition or a cured product thereof (potting material) covers the battery cells while in contact with the front surfaces of the plurality of battery cells (except for the surface of the battery cells in contact with the substrate side) in one example (Fig. 1 structure), or may be in contact with only the upper portions of a plurality of battery cells (structure of FIG. 2).

1 and 2 are schematic diagrams of the structure of the battery module as described above, the substrate 10; It is a view showing a structure including the battery cell 20 and the potting material 30 (the curable composition or a cured product thereof). The battery module may further include an adhesive material 40 for fixing the battery cell 20 to the substrate 10, and in one example, the adhesive material 40 may be configured to have thermal conductivity. .

As long as the curable composition or a cured product thereof is applied as a potting material, the specific configuration of the battery module, for example, the type of the battery cell, substrate and / or adhesive material is not particularly limited, and known materials may be applied. .

For example, a known pouch-shaped, prismatic or cylindrical battery cell may be applied as the battery cell, and a known material may be applied as a substrate or adhesive material.

The manufacturing method of the battery module is not particularly limited, and for example, the curable composition may be poured onto a plurality of battery cells formed on a substrate and, if necessary, cured.

Since the curable composition of the present application has appropriate viscosity and thixotropy, it can efficiently fill the space between battery cells disposed very close to each other, and can exhibit desired heat insulation and heat shielding properties after forming a potting material. .

This application may provide a curable composition and its use. The curable composition of the present application may be applied to a product that generates heat during driving or maintenance to provide a curable composition that can be used as a material capable of treating the heat. The curable composition of the present application is applied to a product in which a plurality of elements generating heat are integrated, and the heat generated by the element can be efficiently treated while maintaining a uniform temperature of the product. In addition, even when the curable composition of the present application is applied to the product as described above and abnormal heat generation, explosion, or ignition occurs in any one element among the plurality of elements, such heat generation, explosion, or ignition is transmitted to other adjacent elements. impact can be prevented or minimized. The curable composition of the present application can also stably perform the above functions over a long period of time.

This application may also provide a cured body formed by the curable composition as above or a use of the curable composition or the cured body.

1 and 2 are schematic diagrams of exemplary battery modules of the present application.

Although the present application is specifically described through the following examples, the scope of the present application is not limited by the following examples.

1. Measurement of latent heat

The latent heat of the cured product or phase change material was evaluated in the following manner. The latent heat of the curing body is determined by mixing the main material and the curing agent part prepared in Examples or Comparative Examples in a volume ratio of 1: 1, leaving the mixture in a chamber at 80 ° C for about 1 hour, and then using an aluminum injector to mix the mixture. It was applied to a dish to a thickness of about 10 mm, maintained at room temperature (about 25° C.) for 24 hours to cure, and the cured product was measured. About 3 to 5 mg of the hardened material or phase change material was taken and the latent heat was evaluated using a Differential Scanning Calorimeter (DSC) equipment (TA instrument, Q200 model). During the evaluation of latent heat, the temperature range was -20°C to 200°C, the endothermic interval was measured while the temperature was raised at a rate of about 10°C/min, and the endothermic peak was integrated to calculate the latent heat (unit: J/g).

In addition, the temperature at the apex of the endothermic peak confirmed in the above analysis was taken as the latent heat temperature. When two or more endothermic peaks were confirmed, the temperature at the apex of the main peak was used as the latent heat temperature.

2. Weight change (ΔW)

The subject and curing agent parts prepared in Example or Comparative Example were mixed in a weight ratio of 1:1 and maintained in a chamber at 80° C. for about 1 hour. Subsequently, the mixture was applied to an aluminum dish with an injector to a thickness of about 10 mm, and cured by maintaining at room temperature (about 25° C.) for about 24 hours. A specimen (weight: W _i , unit g) was prepared by cutting the cured body into a square having a horizontal and vertical length of 1 cm, respectively. The specimen was maintained in a chamber at about 80 ° C. for about 24 hours in a state of being placed on filter paper, and then taken out and the weight of the specimen (weight: W _f , unit g) was measured again. The weight change rate (ΔW) was measured by substituting the weight measured in the above process into Equation A below. The weight change rate was measured for each of four specimens formed of the same curable composition, and the average value thereof is shown in Tables 1 and 2 below.

[Equation A]

ΔW = 100 × (W _f - W _i )/W _i

3. Temperature control performance test

The subject and curing agent parts prepared in Example or Comparative Example were mixed in a weight ratio of 1:1 and maintained in a chamber at 80° C. for about 1 hour. Subsequently, the mixture was applied to an aluminum dish with an injector to a thickness of about 10 mm, and cured by maintaining at room temperature (about 25° C.) for about 24 hours. Subsequently, a specimen was prepared by cutting the cured body into a square having a horizontal and vertical length of 3 cm, respectively. A K-type thermocouple was attached on a hot plate, the specimen was adhered to it, and fixed with tape. Subsequently, the temperature of the hot plate was raised from room temperature to about 35°C at the same heating rate over about 2 minutes, and after maintaining the temperature at 35°C for about 10 minutes, the temperature was raised to 73°C over about 10 minutes at the same heating rate. The temperature was raised. After maintaining the temperature of 73° C. for about 22 minutes, the temperature was measured with the K-type thermocouple.

4. Hardness measurement

The main material and the curing agent part prepared in Example or Comparative Example were mixed in a weight ratio of 1:1, maintained in a chamber at 80 ° C. for about 1 hour, and then the mixture was poured into an aluminum dish with an injector. After applying to a thickness of about 10 mm, it was cured by maintaining at room temperature (about 25 ° C.) for about 24 hours, and the hardness of the cured product was measured according to ASTM D2240 standard. When measuring hardness, an ASKER Durometer device was used. The initial hardness was measured by applying a load of about 1.5 kg to the surface of the sample in a flat state, and the hardness was evaluated by confirming the measured value stabilized after 15 seconds. Shore A or Shore OO hardness was measured.

5. Measurement of Density

The density of the cured body was confirmed using a gas pycnometer (model name: BELPYCNO, manufacturer: MicrotracBEL) according to ASTM D792 standard. Using the above equipment, it is possible to check the density measurement value at room temperature according to the injection of helium gas. The cured body is maintained in a chamber at 80 ° C. for about 1 hour in a state in which the main material and the curing agent part prepared in Examples or Comparative Examples are mixed in a weight ratio of 1: 1, and then the mixture is mixed with an aluminum dish using an injector. It was prepared by applying to a dish to a thickness of about 10 mm and then curing by maintaining at room temperature (about 25 ° C.) for about 24 hours.

6. Gel Permeation Chromatograph (GPC)

The molecular weight characteristics of the materials were measured using GPC (Gel permeation chromatography). Put the material to be analyzed in a 5 mL vial, and dilute in toluene to a concentration of about 5 mg/mL. After that, the standard sample for calibration and the material to be analyzed were filtered through a syringe filter (pore size: 0.45 μm) and then measured. The analysis program used ChemStation from Agilent technologies, and the weight average molecular weight (Mw) or number average molecular weight (Mn) was obtained by comparing the elution time of the sample with a calibration curve. The measurement conditions of GPC are as follows.

<GPC measurement conditions>

Device: 1200 series by Agilent technologies

Column: Use 2 PLgel mixed B from Polymer laboratories

Solvent: Toluene

Column temperature: 40 ℃

Sample concentration: 5 mg/mL, 10 μL injection

Standard samples: Polystyrene (Mp: 3900000, 723000, 316500, 52200, 31400, 7200, 3940, 485)

7. Particle size analysis

The average particle diameter was measured using Marven's MASTERSIZER 3000 equipment in accordance with ISO-13320, and Ethanol was used as a solvent during measurement. As the particle diameter, the D50 particle diameter was measured and this was used as the average particle diameter. The D50 particle diameter is the particle diameter (median diameter) at the volume-based cumulative 50% of the particle size distribution, at the point where the cumulative value is 50% in the cumulative curve where the volume-based particle size distribution is obtained and the total volume is 100%. is the particle diameter.

8. Viscosity analysis

The viscosity of the curable composition was evaluated using a Brookfield viscometer (LV type). The curable composition was put into a 50 mL vial, and the viscosity was measured using the device (measurement conditions: Spindle #63, 10 rpm).

Example 1.

Manufacture of subject parts

As the curable resin component, a silicone resin component (manufactured by KCC, SL3000) was used. The main part of the curable composition was prepared by mixing the main material (SL3000A) of the silicone resin component and a phase change material in the form of a core cell (manufactured by Microtek Laboratories, MPCM43D) as a phase change material. The phase change material (Microtek Laboratories, MPCM43D) includes paraffin having about 22 carbon atoms in the core, and the material of the cell is PMMA (poly (methyl methacrylate)), and has a melting point within the range of about 25 ° C to 50 ° C (or It is a material (average particle diameter: about 125 μm) with a latent heat of about 110 J/g in the latent heat section). The weight average molecular weight (Mw) of the subject (SL3000A) was about 28000 g/mol. During the mixing, about 25 parts by weight of the phase change material was mixed with 100 parts by weight of the main material (SL3000A). When preparing the main part, the main part and the phase change material were stirred at 300 rpm for 1 hour.

Manufacture of curing agent parts

A curing agent part was prepared by mixing a curing agent (SL3000B) of a silicone resin component (manufactured by KCC, SL3000) and a phase change material. As the phase change material, the same material as in the preparation of the main part was used. The weight average molecular weight (Mw) of the curing agent (SL3000B) was about 28000 g/mol. During the mixing, about 25 parts by weight of the phase change material was mixed with 100 parts by weight of the curing agent (SL3000B). When preparing the curing agent part, the curing agent and the phase change material were stirred at 300 rpm for 1 hour.

curable composition

A curable composition was prepared by preparing the subject and curing agent parts in a weight ratio of 1:1. The curable composition is a room temperature curing type, and can be cured by maintaining the curable composition at room temperature for about 12 hours or longer.

Example 2.

Manufacture of subject parts

As the curable resin component, an epoxy resin component was used. The main part of the curable composition was prepared by mixing the main part of the epoxy resin component (Hexion, EPON8111) and the phase change material. The same material as in Example 1 was used as the phase change material. The weight average molecular weight (Mw) of the subject (Hexion, EPON8111) was about 280 g/mol. During the mixing, about 30 parts by weight of the phase change material was mixed with 100 parts by weight of the subject (Hexion, EPON8111). When preparing the main part, the main part and the phase change material were stirred at 300 rpm for 1 hour.

Manufacture of curing agent parts

A curing agent part was prepared by mixing an epoxy resin component curing agent (Hexion Co., EPIKURE 3271) and a phase change material. As the phase change material, the same material as in the preparation of the main part was used. During the mixing, about 50 parts by weight of the phase change material was mixed with 100 parts by weight of the curing agent (EPIKURE 3271). When preparing the curing agent part, the curing agent and the phase change material were stirred at 300 rpm for 1 hour.

curable composition

A curable composition was prepared by preparing the subject and curing agent parts in a weight ratio of 1:1. The curable composition is a room temperature curable type, and can be cured by maintaining the curable composition at room temperature for about 12 hours or more.

Example 3.

Manufacture of subject parts

As the curable resin component, a silicone resin component (manufactured by KCC, SL3000) was used. The main part of the curable composition was prepared by mixing the main part of the silicone resin component (SL3000A) and the phase change material. As the phase change material, the same material as in Example 1 was used. During the mixing, about 60 parts by weight of the phase change material was mixed with 100 parts by weight of the main material (SL3000A). When preparing the main part, the main part and the phase change material were stirred at 300 rpm for 1 hour.

Manufacture of curing agent parts

A curing agent part was prepared by mixing a curing agent (SL3000B) of a silicone resin component (manufactured by KCC, SL3000) and a phase change material. As the phase change material, the same material as in the preparation of the main part was used. In the mixing, about 60 parts by weight of the phase change material was mixed with 100 parts by weight of the curing agent (SL3000B). When preparing the curing agent part, the curing agent and the phase change material were stirred at 300 rpm for 1 hour.

curable composition

A curable composition was prepared by preparing the subject and curing agent parts in a weight ratio of 1:1. The curable composition is a room temperature curing type, and can be cured by maintaining the curable composition at room temperature for about 12 hours or more.

Comparative Example 1.

A subject and a curing agent part and a curable composition were prepared in the same manner as in Example 1, except that the phase change material was not mixed.

Comparative Example 2.

Manufacture of subject parts

As the curable resin component, a silicone resin component (manufactured by KCC, SL3000) was used. The main part of the silicone resin component (SL3000A) was mixed with paraffin (Paraffin C ₁₆ ~ C ₂₈ manufactured by Junsei) having a melting point in the range of about 42 ° C to 44 ° C as a phase change material to prepare a main part. In addition, the phase change material exhibited a latent heat of about 180 J/g in a temperature range of 42° C. to 44° C. in DSC analysis. During the mixing, about 60 parts by weight of the phase change material was mixed with 100 parts by weight of the main material (SL3000A). In the manufacture of the main part, first, the phase change material is melted by uniformly stirring (300 rpm) at a temperature of about 60 ° C. for 1 hour, and the other components of the main part are mixed with the melted phase change material, and then stirred at 500 rpm for 2 hours. Further stirring was performed. Thereafter, a main part was prepared by defoaming by stirring for 20 minutes at 50 rpm in a vacuum atmosphere.

Manufacture of curing agent parts

A curing agent part was prepared by mixing a curing agent (SL3000B) of a silicone resin component (manufactured by KCC, SL3000) and a phase change material. As the phase change material, the same material as in the preparation of the main part was used. In the mixing, about 60 parts by weight of the phase change material was mixed with 100 parts by weight of the curing agent (SL3000B). In the manufacture of the curing agent part, first, the phase change material is melted by uniformly stirring (300 rpm) for 1 hour at a temperature of about 60 ° C., and the other components of the curing agent part are mixed with the molten phase change material, and then stirred at 500 rpm for 2 hours. Further stirring was performed. After that, the main part was prepared by defoaming by stirring for 20 minutes at 50 rpm in a vacuum atmosphere.

curable composition

A curable composition was prepared by preparing the subject and curing agent parts in a weight ratio of 1:1. The curable composition is a room temperature curing type, and can be cured by maintaining the curable composition at room temperature for about 12 hours or longer.

Comparative Example 3.

Manufacture of subject parts

As the curable resin component, a silicone resin component (manufactured by KCC, SL3000) was used. The main part of the curable composition was prepared by mixing the main part of the silicone resin component (SL3000A) and the phase change material. As the phase change material, the same material as in Example 1 was used. During the mixing, about 17 parts by weight of the phase change material was mixed with 100 parts by weight of the main material (SL3000A). When preparing the main part, the main part and the phase change material were stirred at 300 rpm for 1 hour.

Manufacture of curing agent parts

A curing agent part was prepared by mixing a curing agent (SL3000B) of a silicone resin component (manufactured by KCC, SL3000) and a phase change material. As the phase change material, the same material as in the preparation of the main part was used. During the mixing, about 17 parts by weight of the phase change material was mixed with 100 parts by weight of the curing agent (SL3000B). When preparing the curing agent part, the curing agent and the phase change material were stirred at 300 rpm for 1 hour.

curable composition

A curable composition was prepared by preparing the subject and curing agent parts in a weight ratio of 1:1. The curable composition is a room temperature curing type, and can be cured by maintaining the curable composition at room temperature for about 12 hours or longer.

The evaluation results for the above Examples and Comparative Examples are summarized in Tables 1 and 2 below. In Tables 1 and 2 below, the viscosity is measured immediately after mixing when a two-component composition including a main part and a cured body part was prepared in Examples or Comparative Examples.

Example One 2 3 Viscosity (cP @ 23°C) 2400 2200 4500 Latent heat of hardened body (J/g) 27 47 95 Cured body latent heat temperature (℃) 37.2 39.0 38.5 Hardened body density (g/cm ³ ) 0.94 0.97 0.91 hardened body hardness 40~45(shore A) 90 (shore A) 35~40(shore A) Weight change (%) 0.1 0.22 0.25 Temperature control performance (℃) 59 53 50

comparative example One 2 3 Viscosity (cP @ 23°C) 1050 25000 1600 Latent heat of hardened body (J/g) - 170 7.5 Latent heat temperature of hardened body (℃) - 49.7 39.1 Hardened body density (g/cm ³ ) 0.98 0.90 0.99 hardened body hardness 40~45(shoreA) 30~40 (shore A) 40~45(shore A) Weight change (%) 0 4.7 0.05 Temperature control performance (℃) 72 51 67

Claims (18)

Including a curable resin component and a phase change material,
A curable composition satisfying the following condition 1:
[Condition 1]
100 × (W _f - W _i )/W _i ≤ 3%
In condition 1, W _f is the weight of the cured product formed from the curable composition measured after maintaining it at 80° C. for 24 hours, and W _i is the weight of the cured product before maintaining it at 80° C. for 24 hours. The curable composition according to claim 1, which forms a cured body exhibiting a latent heat within a range of 20 to 200 J/g at a latent heat temperature within a temperature range of 0°C to 60°C. The curable composition according to claim 1, wherein the cured body has a density within the range of 0.7 to 1.5 g/ml. The curable composition according to claim 1, wherein the cured body has a Shore OO hardness in the range of 20 to 90 or a Shore A hardness in the range of 10 to 60. The curable composition according to claim 1, wherein the curable resin component has a weight average molecular weight of 9000 g/mol or more. The curable composition according to claim 1, wherein the curable resin component is an acrylic resin component, a polyurethane component, a silicone resin component, or an epoxy resin component. The curable composition according to claim 1, wherein the phase change material is in the form of a core-shell. The curable composition according to claim 7, wherein the core of the phase change material undergoes phase transition between a solid phase and a liquid phase. The curable composition according to claim 7, wherein the core of the phase change material has a melting point within a range of 5°C to 100°C. The curable composition according to claim 7, wherein the phase change material has a latent heat within a range of 50 to 400 J/g at a temperature within a range of 10°C to 100°C. The curable composition according to claim 7, wherein the core of the phase change material includes at least one selected from the group consisting of fatty acids, polyhydric alcohols, ketones, lactic acid, and paraffin. The curable composition according to claim 7, wherein the core of the phase change material has a melting point within a range of 5°C to 100°C and contains paraffin having 5 or more carbon atoms. The method of claim 7, wherein the cell of the phase change material, fatty acid; acrylic polymer; acrylic polymer and n-hexadecane; acrylic polymer and polyethylene glycol; or a curable composition containing polyvinyl alcohol and tetradecane. The curable composition according to claim 7, wherein the phase change material has an average particle diameter of 500 μm or less. The curable composition according to claim 1, comprising 20 to 100 parts by weight of a phase change material based on 100 parts by weight of the curable resin component. According to claim 1, aluminum hydroxide (Al (OH) ₃ ), magnesium hydroxide (Mg (OH) ₂ ), calcium hydroxide (Ca (OH) ₂ ), boehmite (AlOOH), hydromagnesite, magnesia, alumina, nitride At least one selected from the group consisting of aluminum (AlN, aluminum nitride), boron nitride (BN), silicon nitride (Si3N4, silicon nitride), silicon carbide (SiC), zinc oxide (ZnO), and beryllium oxide (BeO) A curable composition further comprising a filler. A cured product of the curable composition according to any one of claims 1 to 16. A product comprising a heat-generating component and the curable composition of claim 1 or the cured product of claim 17 present adjacent to the heat-generating component.

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