Epoxy resin composition and manufacturing method

Abstract

Embodiments of the present disclosure generally relate to epoxy resin compositions, methods of making epoxy resin compositions, and uses of epoxy resin compositions. In an embodiment, the composition includes an epoxy resin, a latent catalytic curing agent, and a filler. The composition may be used in an article. In an embodiment, an article includes a heat generating member and a composition disposed on the heat generating member, the composition including an epoxy resin, a latent catalytic curing agent, and a filler.

Description

Technical Field

[0001] This application claims the benefit of and priority to U.S. patent application No. 18 / 108,460, filed February 10, 2023, which is incorporated herein by reference in its entirety.

[0002] Embodiments of the present disclosure generally relate to epoxy resin compositions, methods of making epoxy resin compositions, and uses of epoxy resin compositions. Background Art

[0003] As the demand for electrical devices such as electric motors, generators, vehicle components, and other components increases, thermal management of these devices continues to receive increasing attention. As power density increases, the amount of heat that needs to be dissipated also increases, making proper thermal management crucial. Ineffective or insufficient thermal management can lead to poor device performance and shortened lifespan, as overheating can damage materials, create cracks, and deform structures within and around the device. Safety can also be negatively impacted. Therefore, proper thermal management of electrical devices is necessary to improve their reliability, performance, safety, and lifespan.

[0004] While several thermal management technologies are known, such as resin compositions, heat sinks, thermoelectric coolers, forced air systems, and others, these technologies have varying degrees of effectiveness. For example, the equipment required for thermoelectric coolers and forced air systems is bulky, heavy, and expensive. Such size and complexity are prohibitive in many applications. Conventional resin compositions for thermal management are two-component (2K) systems that require on-site mixing. Furthermore, the thermal conductivity of conventional resin compositions is too low for effective thermal management of electrical devices.

[0005] Therefore, there is a need for new and improved compositions for thermal management. Summary of the Invention

[0006] Embodiments of the present disclosure generally relate to epoxy resin compositions, methods of making epoxy resin compositions, and uses of epoxy resin compositions. The embodiments described herein can be used for thermal management of various electrical devices and equipment.

[0007] In one embodiment, an article is provided. The article includes a heat-generating component. The article further includes a composition disposed on the heat-generating component, the composition comprising: an aromatic epoxy resin; a latent catalytic curing agent, the latent catalytic curing agent being active at a temperature of about 30° C. to about 300° C.; and a filler.

[0008] In another embodiment, an article is provided. The article includes a heat generating component. The article further includes a heat dissipation component disposed on a surface of the heat generating component, the heat dissipation component comprising a curable composition, the curable composition comprising an epoxy polymerization product of a curable composition, the curable composition comprising: an aromatic epoxy resin in an amount of approximately 20 wt% to 70 wt% based on the total wt% of the curable composition; a filler in an amount of approximately 30 wt% to approximately 80 wt% based on the total wt% of the curable composition; and a latent catalytic curing agent in an amount greater than 0 wt% and less than approximately 10 wt%, wherein the total wt% of the curable composition does not exceed 100 wt%.

[0009] In another embodiment, a method for forming an article is provided. The method includes placing a curable composition comprising an aromatic epoxy resin, a latent catalytic curing agent, and a filler in a mold. The method further includes heating the mold and the curable composition to form a cured composition. The method further includes placing the cured composition on a heat-generating component to form the article.

[0010] In another embodiment, a composition for thermal management is provided, which includes an aromatic epoxy resin, a latent catalytic curing agent, and a filler.

[0011] In another embodiment, a curable composition comprising an epoxy polymerization product of a curable composition is provided. The curable composition includes: an aromatic epoxy resin in an amount of about 20 to 70 wt %, based on the total wt % of the curable composition; a filler in an amount of about 30 to about 80 wt %, based on the total wt % of the curable composition; and a latent catalytic curing agent in an amount greater than about 0 wt % and less than about 10 wt %, wherein the total wt % of the curable composition does not exceed 100 wt %, and the curable composition is used to cover at least a portion of a heat-generating device, heat-generating equipment, or a component thereof.

[0012] In another embodiment, a method for forming a cured composition for thermal management is provided. The method includes heating a curable composition at a first temperature, the curable composition comprising an aromatic epoxy resin, a latent catalytic curing agent, and a filler. The method further includes placing the heated curable composition in a mold, and heating the mold and the curable composition at a second temperature to form the cured composition, wherein the first temperature and the second temperature are the same or different. BRIEF DESCRIPTION OF THE DRAWINGS

[0013] none DETAILED DESCRIPTION

[0014] Embodiments of the present disclosure generally relate to epoxy resin compositions, methods for making epoxy resin compositions, and uses of epoxy resin compositions. The compositions described herein can be used to thermally manage various articles, devices, apparatuses, or components thereof by removing heat generated by the apparatus, apparatus, or components thereof. "Thermal management" refers to the ability to maintain temperature-sensitive components within or around electronic / electrical items within specified operating temperatures to avoid failure. In some embodiments, the composition is a thermally conductive composition. The term "thermal conductivity" refers to the property of a material to transfer or transmit thermal energy or heat to another component or to itself.

[0015] In general, the composition can be used with a heat generating component such as an electrical device, an electronic device, an electrical apparatus, an electronic device, or a component thereof. For example, the composition (or cured composition) described herein can directly or indirectly contact a heat generating component such as an electrical or electronic component. Because the composition (or cured composition) is thermally conductive, the composition (or cured composition) can remove heat generated by the electrical or electronic component.

[0016] The inventors have discovered new and improved compositions that are easy to use and have good thermal conductivity. Unlike conventional compositions for thermal management (typically 2K systems that require on-site mixing), the embodiments described herein can be one-component systems because polymerization does not occur before a stimulus (such as heat) is applied. For example, the compositions of the present disclosure can include an epoxy resin, a catalytic curing agent, a filler, and optionally, additives. Upon application of a stimulus (such as heat), the latent catalytic curing agent can cause, for example, a polyaddition reaction to occur, resulting in coupling, crosslinking, or both of the epoxy resin and other materials. Such compositions can be curable compositions that can be stored under ambient conditions. Conventional compositions for thermal management lack such capabilities because they are not one-component systems.

[0017] Due to the thermal conductivity of the compositions described herein, for example, the compositions of the present disclosure can be used to remove or dissipate heat from heating elements or components. Such heating elements or components are present in, for example, electrical equipment, electronic equipment, electrical devices, and electronic devices. Therefore, in some embodiments, an article includes a heating element and a composition of the present disclosure disposed on the heating element. The composition can be disposed on one or more surfaces and can directly or indirectly contact the one or more surfaces.

[0018] Headings are used for convenience only and do not limit the scope of the disclosure.The embodiments described herein can be combined with other embodiments.

[0019] As used herein, a "composition" can include a component of the composition, a reaction product of two or more components of the composition, a balance of remaining starting components, or a combination thereof. The compositions of the present disclosure can be prepared by any suitable mixing process.

[0020] Composition

[0021] Embodiments of the present disclosure generally relate to compositions that can be used for thermal management of heat-generating devices, heat-generating equipment, or components thereof. For example, the compositions can be used as casting compositions (reaction compositions), molding compositions (reaction resin compositions), as prepregs, and in other applications. The compositions can be used in electrical engineering, for example, for coating electrical and electronic components such as capacitors, current collectors, and resistors.

[0022] As described herein, the inventors have discovered compositions having higher thermal conductivity than conventional compositions. In some embodiments, the compositions can be used for thermal management of various devices and equipment. Specifically, the compositions can be used to dissipate heat from heat-generating devices, heat-generating equipment, or components thereof, such as electrical and electronic devices, equipment, or components thereof, such as electric motors. In this manner, the compositions can improve the reliability, performance, safety, and lifespan of devices and equipment.

[0023] The composition of the present disclosure may include an epoxy resin, a catalytic curing agent, and a filler. In some embodiments, the composition may further include one or more additives. The total weight percentage (total wt%) of the composition does not exceed 100 wt%. In at least one embodiment, the composition includes an epoxy resin comprising an aromatic epoxy resin; a latent catalytic curing agent, the latent catalytic curing agent being active at a temperature of about 30° C. to about 300° C.; and a filler.

[0024] The compositions may be curable compositions, wherein the composition can be cured by applying a stimulus such as a change in temperature.

[0025] Epoxy resins are compounds containing at least one vicinal epoxy group. Epoxy resins can be monomeric or polymeric. Epoxy resins can be saturated or unsaturated, aliphatic, cycloaliphatic, aromatic, or heterocyclic, and can be substituted. In some instances, the epoxy resin is selected based on, for example, the desired UV resistance.

[0026] The epoxy resin utilized may be, for example, an epoxy resin prepared from epihalohydrin and phenol or a phenolic compound, or an epoxy resin prepared from epihalohydrin and an amine, or an epoxy resin prepared from an epihalohydrin and a carboxylic acid, or an epoxy resin prepared by oxidation of an unsaturated compound, or a combination of epoxy resins.

[0027] Suitable epoxy resins that can be used in the embodiments described herein may include aromatic epoxy resins and non-aromatic epoxy resins. The epoxy resin may contain more than one and in some embodiments, two 1,2-epoxy groups per molecule. In some embodiments, the epoxy resin may be liquid rather than solid. In at least one embodiment, the epoxy resin has an epoxide equivalent weight of about 100 to about 5,000, such as about 100 to about 2,000, such as about 100 to 500, as determined by the titration method described in ASTM D1652.

[0028] In some embodiments, the epoxy resin may be a non-aromatic hydrogenated cyclohexanedimethanol and diglycidyl ether of a hydrogenated bisphenol A type epoxy resin, such as hydrogenated bisphenol A-epichlorohydrin epoxy resin, cyclohexanedimethanol diglycidyl ether, and a cycloaliphatic epoxy resin.

[0029] In at least one embodiment, the epoxy resin utilized comprises an aromatic epoxy resin, such as those produced from epihalohydrins and phenol or phenolic compounds. Phenolic compounds include compounds having an average of more than one aromatic hydroxyl group per molecule. Examples of phenolic compounds include dihydroxyphenols, biphenols, bisphenols, halogenated biphenols, halogenated bisphenols, hydrogenated bisphenols, alkylated biphenols, alkylated bisphenols, trisphenols, phenol-aldehyde resins, novolac resins (reaction products of phenol with simple aldehydes such as formaldehyde), halogenated phenol-aldehyde novolac resins, substituted phenol-aldehyde novolac resins, phenol-hydrocarbon resins, substituted phenol-hydrocarbon resins, phenol-hydroxybenzaldehyde resins, alkylated phenol-hydroxybenzaldehyde resins, hydrocarbon-phenol resins, hydrocarbon-halogenated phenol resins, hydrocarbon-alkylated phenol resins, or combinations thereof.

[0030] In some embodiments, the epoxy resins utilized may include those derived from epihalohydrins and bisphenols, halogenated bisphenols, hydrogenated bisphenols, novolac resins, and polyalkylene glycols, or combinations thereof.

[0031] In at least one embodiment, the epoxy resin utilized in the composition of the present disclosure preferably includes those derived from epihalohydrin and resorcinol, catechol, hydroquinone, biphenol, bisphenol A, bisphenol AP (1,1-bis(4-hydroxyphenyl)-1-phenylethane), bisphenol F, bisphenol K, tetrabromobisphenol A, phenol-aldehyde novolac resins, alkyl-substituted phenol-aldehyde resins, phenol-hydroxybenzaldehyde resins, cresol-hydroxybenzaldehyde resins, dicyclopentadiene-phenol resins, dicyclopentadiene-substituted phenol resins tetramethylbiphenol, tetramethyl-tetrabromobiphenol, tetramethyltribromobiphenol, tetrachlorobisphenol A, or combinations thereof.

[0032] In some embodiments, the epoxy resins utilized in the compositions of the present disclosure include those derived from epihalohydrins and amines. Suitable amines include diaminodiphenylmethane, aminophenol, xylenediamine, aniline, and the like, or combinations thereof.

[0033] In at least one embodiment, the epoxy resin utilized in the composition of the present disclosure may include those resins produced from epihalohydrins and carboxylic acids. Suitable carboxylic acids include phthalic acid, isophthalic acid, terephthalic acid, tetrahydrophthalic acid, hexahydrophthalic acid, endomethylenetetrahydrophthalic acid, isophthalic acid, methylhexahydrophthalic acid, and the like, or combinations thereof.

[0034] In some embodiments, the epoxy resin compound utilized in the composition of the present disclosure includes those resins produced by epihalohydrin and a compound having at least one aliphatic hydroxyl group. In such embodiments, it should be understood that the resin composition produced contains an average of more than one aliphatic hydroxyl group. Examples of compounds having at least one aliphatic hydroxyl group per molecule include aliphatic alcohols, aliphatic diols, polyether diols, polyether triols, polyether tetraols, any combination thereof, and the like. Alkylene oxide adducts containing a compound having at least one aromatic hydroxyl group are also suitable. In this embodiment, it should be understood that the resin composition produced contains an average of more than one aromatic hydroxyl group. Examples of oxide adducts of compounds containing at least one aromatic hydroxyl group per molecule include ethylene oxide, propylene oxide or butylene oxide adducts of dihydric phenols, biphenols, bisphenols, halogenated bisphenols, alkylated bisphenols, trisphenols, phenol-aldehyde novolac resins, halogenated phenol-aldehyde novolac resins, alkylated phenol-aldehyde novolac resins, hydrocarbon-phenol resins, hydrocarbon-halogenated phenol resins or hydrocarbon-alkylated phenol resins, or combinations thereof.

[0035] In some embodiments, the epoxy resin may refer to an advanced epoxy resin, which is the reaction product of one or more epoxy resin components as described above with one or more phenolic compounds and / or one or more compounds having an average of more than one aliphatic hydroxyl group per molecule as described above. Alternatively, the epoxy resin may be reacted with a carboxyl-substituted hydrocarbon. A carboxyl-substituted hydrocarbon is described herein as having a hydrocarbon backbone, such as a C1-C 40 A compound having a hydrocarbon backbone and one or more, such as more than one, such as two, carboxyl moieties. 40 The hydrocarbon backbone can be a straight or branched alkane or alkene, optionally containing oxygen. Fatty acids and fatty acid dimers are among the useful carboxylic acid-substituted hydrocarbons. Fatty acids include caprylic acid, caprylic acid, caprylic acid, octanoic acid, pivalic acid, neodecanoic acid, capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, palmitoleic acid, oleic acid, linoleic acid, linolenic acid, erucic acid, pentadecanoic acid, heptadecanoic acid, arachidic acid, and their dimers.

[0036] In at least one embodiment, the epoxy resin is the reaction product of a polyepoxide and a compound containing more than one isocyanate moiety or a polyisocyanate. The epoxy resin produced in such a reaction may be an epoxy-terminated polyoxazolidinone.

[0037] In some embodiments, the epoxy resin includes cyclohexanol, polymer of 4,4'-(1-methylethylene)bis-, and 2-(chloromethyl)oxirane (CAS No. 30583-72-3).

[0038] Examples of epoxy resins include epoxy resins of dihydric phenols, epoxy resins of biphenols, epoxy resins of bisphenols, epoxy resins of halogenated bisphenols, epoxy resins of alkylated bisphenols, epoxy resins of trisphenols, epoxy resins of phenol-aldehyde novolac resins, epoxy resins of halogenated phenol-aldehyde novolac resins, epoxy resins of alkylated phenol-aldehyde novolac resins, epoxy resins of hydrocarbon-phenol resins, epoxy resins of hydrocarbon-halogenated phenol resins, epoxy resins of hydrocarbon-alkylated phenol resins, or combinations thereof. Illustrative but non-limiting examples of epoxy resins include Epikote 1001 epoxy resin (bisphenol A-based epoxy resin), Epikote 1004 epoxy resin (bisphenol A-based epoxy resin), Epikote 1007 epoxy resin (bisphenol A-based epoxy resin), Epikote 1009 epoxy resin (bisphenol A-based epoxy resin), Epon SU8 epoxy resin (epoxidized bisphenol A novolac), Epon 1031 epoxy resin (epoxidized glyoxal-phenol novolac), Epon 1163 epoxy resin (tetrabromobisphenol A-based epoxy resin), Epikote 03243 / LV epoxy resin (epoxy resin based on (3,4-epoxycyclohexyl)methyl formate and bisphenol A), and Epon 164 epoxy resin (epoxidized o-cresol novolac)—all available from Hexion Inc. is commercially available.

[0039] In at least one embodiment, the aromatic epoxy resin may be selected from the group consisting of difunctional bisphenol-A-diepoxypropyl-ether, bisphenol-F-diepoxypropyl-ether, tetraepoxypropyl-methylene-diphenylamine, epoxidized tetraphenylethane, derivatives thereof, and combinations thereof. In some embodiments, the aromatic epoxy resin may be derived from bisphenol A, bisphenol F, tetraepoxypropyl-methylene-diphenylamine, halogenated bisphenols, novolacs, o-aminophenols, p-aminophenols, furanone bisphenols, dicyclopentadiene, or combinations thereof.

[0040] Other illustrative but non-limiting examples of epoxy resins include Epikote 828LVEL epoxy resin (difunctional bisphenol-A-diglycidyl-ether, commercially available from Westlake Epoxy), Epikote 162 epoxy resin (bisphenol-F-diglycidyl-ether, commercially available from Westlake Epoxy), Epikote 158 epoxy resin (bisphenol-F-diglycidyl-ether, commercially available from Westlake Epoxy), Epikote 496 epoxy resin (tetraglycidyl-methylene-diphenylamine, commercially available from Westlake Epoxy), Epikote 1031 epoxy resin (tetraphenylethane epoxidation, commercially available from Westlake Epoxy).

[0041] In some embodiments, an epoxy resin having as high an aromatic content as possible may be selected. For example, the epoxy resin may include an aromatic epoxy resin, such as an epoxy resin including phenol, phenyl, combinations thereof, or other aromatic moieties. A higher aromatic content may provide the composition with increased thermal conductivity.

[0042] In at least one embodiment, based on the total weight % of the aromatic epoxy resin, the aromatic epoxy resin may have an aromatic content of about 30 wt % to about 70 wt %, such as about 40 wt % to about 60 wt %, such as about 40 wt % to about 55 wt %. In some embodiments, based on the wt % of the aromatic epoxy resin, the aromatic content (wt %) in the aromatic epoxy resin may be 30, 35, 40, 45, 50, 55, 60, 65 or 70, or a range thereof. Each of the aforementioned numbers may be preceded by the words "about", "at least about", "less than about" or "greater than about", and any of the aforementioned numbers may be used alone to describe an open range or in combination to describe a closed range. Other amounts of epoxy resins may be considered.

[0043] The aromatic content of the aromatic epoxy resin is calculated by multiplying the molar weight of the aromatic structure (C6H4=76 g / mol) by the number of aromatic rings in the aromatic epoxy resin and then dividing the result by the total molecular weight of the aromatic epoxy resin.

[0044] Combinations or blends of epoxy-based polymers in any suitable proportions can be used in the compositions described herein.

[0045] Based on the total wt % of the composition, the total amount of epoxy resin in the composition described herein may be from about 20 weight % (wt %) to about 70 wt %, such as from about 25 wt % to about 65 wt %, such as from about 30 wt % to about 60 wt %, such as from about 35 wt % to about 55 wt %, such as from about 40 wt % to about 50 wt %. In some embodiments, based on the total wt % of the composition, the total amount (wt %) of epoxy resin in the composition described herein may be 20, 25, 30, 35, 40, 45, 50, 55, 60, 65 or 70 or a range thereof. Each of the aforementioned numbers may be preceded by the words "about", "at least about", "less than about" or "greater than about", and any of the aforementioned numbers may be used alone to describe an open range or in combination to describe a closed range. Other amounts of epoxy resin may be considered.

[0046] The composition described herein further includes a catalytic curing agent. The catalytic curing agent may be a latent catalytic curing agent (also referred to as a "latent catalyst"). The latent catalytic curing agent can control the start of polymerization and simplify operation. For example, the use of a latent catalyst avoids the in-situ addition and mixing problems of highly reactive chemical substances. The latent catalyst can be stored together without premature reaction, thereby enabling the use of a single-component formulation prepared for polymerization by applying an appropriate stimulus. The latent catalytic curing agent reacts to temperatures above ambient temperature and becomes active, as further described below.

[0047] When a latent catalytic curing agent is described as being "active" at a selected temperature or temperature range, the term "active" refers to a latent catalytic curing agent that causes a reaction (e.g., polyaddition) between one or more components of the composition when the temperature is set to the selected temperature or temperature range.

[0048] A stimulus such as heat acts on the materials of the composition (eg, the latent catalytic curing agent). Upon application of the stimulus, the latent catalytic curing agent causes a polyaddition reaction to occur, resulting in coupling, crosslinking, or both, of the epoxy resin and other materials.

[0049] Conventional compositions for thermal management typically utilize non-latent catalytic curing agents, i.e., they initiate curing at ambient temperature and rapidly cause the formulation viscosity to increase. Consequently, such conventional compositions are made from 2K systems, where two or more components need to be mixed on-site. In contrast, the compositions described herein can be single-component systems (1K systems) because polymerization does not occur until a stimulus (e.g., heat) is applied. 1K systems already contain all necessary ingredients and are storage-stable. It is also contemplated that the compositions described herein are suitable as storable components of 2K systems or other multi-component systems.

[0050] Suitable latent catalytic curing agents (also referred to as "latent catalysts") may include imidazoles, substituted imidazoles, imidazole adducts, imidazole complexes (e.g., Ni-imidazole complexes), tertiary amines, quaternary ammonium compounds, quaternary phosphonium compounds, dicyandiamide, salicylic acid, urea, urea derivatives, boron trifluoride complexes, boron trichloride complexes (e.g., boron trichloride alkylamine complexes), epoxy addition reaction products, tetraphenylene-boron complexes, boric acid amines, metal halides, titanamides, metal acetylacetonates, metal naphthenates, metal octoates, other metal salts, metal chelates, or combinations thereof. Latent catalytic curing agents may include, for example, boron trichloride dimethyloctylamine complex (CAS No. 34762-90 -8), oligomeric polyethylene piperazine, bis-(dimethylaminopropyl)-amino-2-propanol, N,N'-bis-(3-dimethylaminopropyl) urea, N-(2-hydroxypropyl)imidazole, dimethyl-2-(2-aminoethoxy)ethanol, bis(2-dimethylaminoethyl) ether, pentamethylethylenetriamine, di-N-morpholinodiethyl ether, 1,8-diazobicyclo[5.4.0]undec-7-ene (DBU) (CAS No. 6674-22-2), N-methylimidazole (also known as 1-methylimidazole (CAS No. 616-47-7), 1,2-dimethylimidazole, triethylenediamine, 1,1,3,3-tetramethylguanidine, tin(IV) chloride, tin octoate, or a combination thereof.

[0051] In some embodiments, the latent catalytic curing agent does not contain anhydrides, acid anhydrides, or a combination thereof. Anhydrides and acid anhydrides are of concern due to their respiratory sensitization effects.

[0052] Suitable latent catalytic curing agents may include sulfonium salts of formula (I), sulfonium salts of formula (II), sulfonium salts of formula (III), sulfonium salts of formula (IV), or combinations thereof:

[0053]

[0054] In each of formulae (I)-(IV), each R group may be an unsubstituted hydrocarbon group, a substituted hydrocarbon group, or a functional group comprising at least one element from Groups 13 to 17 of the Periodic Table of the Elements. When the R group is a functional group comprising at least one element from Groups 13 to 17, the R group may be a halogen (F, Cl, Br, or I), O, N, Se, Te, P, As, Sb, S, B, Si, Ge, Sn, Pb, and the like, such as C(O)R*, C(C)NR*2, C(O)OR*, NR*2, OR*, SeR*, TeR*, PR*2, AsR*2, SbR*2, SR*, SO x(wherein x = 2 or 3), BR*2, SiR*3, GeR*3, SnR*3, PbR*3 and the like, wherein R* can independently be hydrogen or an unsubstituted hydrocarbon group, or wherein at least one heteroatom has been inserted into the unsubstituted hydrocarbon group.

[0055] "Unsubstituted hydrocarbyl" refers to a group consisting solely of hydrogen and carbon atoms. Non-limiting examples of unsubstituted hydrocarbyl groups include alkyl groups having 1 to 20 carbon atoms, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, secondary and tertiary butyl, pentyl, hexyl, heptyl, octyl, ethyl-2-hexyl, isooctyl, nonyl, n-decyl, isodecyl, or isomers thereof; cycloaliphatic groups having 3 to 20 carbon atoms, such as cyclopentyl or cyclohexyl; aromatic groups having 6 to 20 carbon atoms, such as phenyl or naphthyl; or any combination thereof. Any of the foregoing numbers can be used alone to describe an open range or in combination to describe a closed range.

[0056] "Substituted hydrocarbyl" refers to an unsubstituted hydrocarbyl group in which at least one hydrogen of the unsubstituted hydrocarbyl group has been replaced by at least one heteroatom or heteroatom-containing group, such as one or more elements from Groups 13-17 of the Periodic Table of the Elements, such as halogens (F, Cl, Br, or I), O, N, Se, Te, P, As, Sb, S, B, Si, Ge, Sn, Pb, and the like, such as C(O)R*, C(C)NR*2, C(O)OR*, NR*2, OR*, SeR*, TeR*, PR*2, AsR*2, SbR*2, SR*, SO x (wherein x=2 or 3), BR*2, SiR*3, GeR*3, SnR*3, PbR*3 and the like, wherein R* is independently hydrogen or an unsubstituted hydrocarbon group, or wherein at least one heteroatom has been inserted into the unsubstituted hydrocarbon group.

[0057] In each of formula (I)-(IV), each R group can independently have any suitable number of carbon atoms, such as 1 to 20 carbon atoms, such as 1 to 12 carbon atoms, such as 1 to 10 carbon atoms, such as 1 to 8 carbon atoms, such as 1 to 5 carbon atoms, 1 to 4 carbon atoms or 3 to 8 carbon atoms. In some embodiments, the number of carbon atoms in each R group of formula (I)-(IV) can independently be 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19 or 20. Each of the aforementioned numbers can be preceded by the word "about", "at least about", "less than about" or "greater than about", and any of the aforementioned numbers can be used alone to describe an open range or used in combination to describe a closed range. Each R group of formula (I)-(IV) can independently be straight or branched, saturated or unsaturated, cyclic or acyclic, aromatic or non-aromatic. With respect to the degree of saturation, each R group of formulae (I)-(IV) may independently be fully saturated, partially unsaturated, or fully unsaturated.

[0058] In some embodiments, each R group of formula (I)-(IV) can independently be C1-C12 alkyl, C3-C8 cycloalkyl, C4-C10 cycloalkylalkyl or phenyl, which is unsubstituted or mono- or poly-substituted by C1-C8 alkyl, C1-C4 alkoxy, halogen, hydroxy, nitro, phenyl, phenoxy, alkoxycarbonyl having 1-4 carbon atoms or acyl having 1-12 carbon atoms.

[0059] In some embodiments, Ar, Ar of formula (I)-(IV) 1 or Ar 2 Each of Ar, Ar in formula (I)-(IV) is aromatic. 1 or Ar 2 Each of the R groups may be independently monocyclic, polycyclic or heterocyclic, and may be unsubstituted or substituted. In at least one embodiment, when substituted, the monocyclic, polycyclic or heterocyclic rings may be independently substituted (mono- or polysubstituted) with one or more R groups, such as those described above.

[0060] In some embodiments, Ar, Ar 1 or Ar 2 Each of the above may independently be phenyl, naphthyl or fluorenyl, wherein the phenyl, naphthyl or fluorenyl is unsubstituted or mono- or poly-substituted by C1-C8 alkyl, C1-C4 alkoxy, halogen, hydroxy, nitro, phenyl, phenoxy, alkoxycarbonyl having 1 to 4 carbon atoms or acyl having 1 to 12 carbon atoms.

[0061] In some embodiments, each arylene group of formula (I)-(IV) is aromatic. In at least one embodiment, each arylene group of formula (I)-(IV) can independently be monocyclic, polycyclic, or heterocyclic, and can be unsubstituted or substituted. In some examples, when substituted, the monocyclic, polycyclic, or heterocyclic ring can independently be substituted (mono- or poly-substituted) with one or more R groups (such as those described above). In some embodiments, each arylene group of formula (I)-(IV) can independently be phenylene, naphthylene, or fluorenylene, wherein the phenylene, naphthylene, or fluorenylene group is unsubstituted or mono- or poly-substituted with C1-C8 alkyl, C1-C4 alkoxy, halogen, hydroxy, nitro, phenyl, phenoxy, alkoxycarbonyl having 1-4 carbon atoms, or acyl having 1-12 carbon atoms.

[0062] In some embodiments, each Q in formula (I)-(IV) - The counter ion may have the formula MX - , wherein M is a metal or metalloid, and X is a group containing at least one element of Groups 13-17, such as halogen (F, Cl, Br, or I), O, N, P, S, B, Si, and others. Illustrative but non-limiting examples of M may include antimony (Sb), silver (Ag), and other metals or metalloids. Illustrative but non-limiting examples of X may include fluorine (F), hydroxyl (OH), and combinations thereof. Q - Examples may include but are not limited to SbF6 - 、AsF6 - or SbF5OH - .

[0063] In formula (I) and (II), there is only one counter ion, such as Q - In formula (III) and (IV), there are two counter ions, such as 2Q - shown.

[0064] In each of formulae (I)-(IV), when there is more than one R, each R may be the same or different. In each of formulae (I)-(IV), when there is more than one Ar, Ar 1 or Ar 2 When Ar, Ar 1 or Ar 2 Each of Q can be the same or different. In each of formulas (I)-(IV), when there is more than one Q - When each Q - Can be the same or different.

[0065] In at least one embodiment, the latent catalytic curing agent is selected from the group consisting of sulfonium salts of formula (I), sulfonium salts of formula (II), sulfonium salts of formula (III), sulfonium salts of formula (IV), and combinations thereof. In these and other embodiments, each R group of formula (I)-(IV) is independently C1-C12 alkyl, C3-C8 cycloalkyl, C4-C10 cycloalkylalkyl, or phenyl, which is unsubstituted or monosubstituted or polysubstituted with C1-C8 alkyl, C1-C4 alkoxy, halogen, hydroxy, nitro, phenyl, phenoxy, alkoxycarbonyl having 1-4 carbon atoms, or acyl having 1-12 carbon atoms; Ar, Ar of formula (I)-(IV) are independently C1-C12 alkyl, C3-C8 cycloalkyl, C4-C10 cycloalkylalkyl, or phenyl. 1 or Ar 2 Each of the Q in Formulas (I) to (IV) is independently phenyl, naphthyl, or fluorenyl, wherein the phenyl, naphthyl, or fluorenyl groups are unsubstituted or mono- or poly-substituted with C1-C8 alkyl, C1-C4 alkoxy, halogen, hydroxy, nitro, phenyl, phenoxy, alkoxycarbonyl groups having 1 to 4 carbon atoms, or acyl groups having 1 to 12 carbon atoms; each arylene group in Formulas (III) and (IV) is independently phenylene, naphthylene, or fluorenyl, wherein the phenylene, naphthylene, or fluorenyl groups are unsubstituted or mono- or poly-substituted with C1-C8 alkyl, C1-C4 alkoxy, halogen, hydroxy, nitro, phenyl, phenoxy, alkoxycarbonyl groups having 1 to 4 carbon atoms, or acyl groups having 1 to 12 carbon atoms; and each Q in Formulas (I) to (IV) is independently phenylene, naphthylene, or fluorenyl, wherein the phenylene, naphthylene, or fluorenyl groups are unsubstituted or mono- or poly-substituted with C1-C8 alkyl, C1-C4 alkoxy, halogen, hydroxy, nitro, phenyl, phenoxy, alkoxycarbonyl groups having 1 to 4 carbon atoms, or acyl groups having 1 to 12 carbon atoms; - Independently SbF6 - 、AsF6 - or SbF5OH - .

[0066] Combinations or blends of latent catalytic curing agents in any suitable ratio may be used in the compositions described herein.

[0067] The total amount of latent catalytic curing agent in the composition described herein can be greater than 0 wt %, less than 10 wt % or a combination thereof, such as about 0.1 wt % to about 3 wt %, such as 0.05 wt % to about 1.5 wt %, such as about 0.1 wt % to about 1 wt %, such as about 0.2 wt % to about 0.9 wt %, such as about 0.3 wt % to about 0.8 wt %, such as about 0.4 wt % to about 0.7 wt %, such as about 0.5 wt % to about 0.6 wt %, based on the total wt % of the composition. In some embodiments, the total amount (wt %) of the latent catalytic curing agent in the composition described herein can be 0.1, 0.2, 0.3, 0.4, 0.5, 0.6, 0.7, 0.8, 0.9, 1, 1.1, 1.2, 1.3, 1.4, 1.5, 1.6, 1.7, 1.8, 1.8, 1.9, 2, 2.1, 2.2, 2.3, 2.4, 2.5, 2.6, 2.7, 2.8, 2.9 or 3, 4, 5, 6, 7, 8, 9, 10 or a range thereof, based on the total wt % of the composition. Each of the aforementioned numbers can be preceded by the words "about," "at least about," "less than about," or "greater than about," and any of the aforementioned numbers can be used alone to describe an open range or in combination to describe a closed range. Other amounts of latent catalytic curing agent are contemplated.

[0068] The compositions described herein may further include a thermally conductive filler, such as a filler having a thermal conductivity of about 0.5 W / mK or greater (W / mK is the number of watts conducted per degree Kelvin per meter of thickness), about 400 W / mK or less, or a combination thereof. In some embodiments, the filler may be a material having a thermal conductivity of about 0.5 W / mK to about 400 W / mK, such as about 1 W / mK to about 100 W / mK, such as about 10 W / mK to about 50 W / mK. In some examples, the thermal conductivity (in W / mK) of the filler can have a low of about 0.5, 1, 1.5, 2, 2.5, 3, 3.5, 4, 4.5, 5, 5.5, 6, 6.5, 7, 7.5, 8, 8.5, 9, 9.5, 10, 10.5, 11, 11.5, 12, 12.5, 13, 13.5, 14, 14.5, or 15, to a high of about 400, 350, 300, 250, 200, 150, 100, 90, 80, 70, 60, 50, 40, 30, 20, or 15. Other thermal conductivities of the filler are contemplated. Each of the aforementioned numbers can be preceded by the words "about," "at least about," "less than about," or "greater than about," and any of the aforementioned numbers can be used alone to describe an open-ended range or in combination to describe a closed range. Here, for example, the thermal conductivity of the filler may be greater than about 2 W / mK, less than about 100 W / mK, about 50 W / mK or greater, about 10 W / mK or less, about 0.5 to about 10 W / mK, or about 30 W / mK to about 50 W / mK.

[0069] Illustrative but non-limiting examples of fillers include silica, wollastonite (CaSiO3, which may contain small amounts of iron, magnesium, and manganese), quartz, alumina, aluminum nitride (AlN), boron nitride (BN), silicon nitride (SiN), silicon carbide (SiC), beryllium oxide (BeO), and combinations thereof. Generally, ceramic materials can be used. Other fillers are contemplated. In some embodiments, carbon fillers such as graphite may also be considered if insulation properties can be ensured.

[0070] In some examples, the filler can include an epoxy-silane pretreated material, such as an epoxy-silane pretreated version of the above fillers, such as epoxy-silane pretreated silica, epoxy-silane pretreated wollastonite, or a combination thereof. An illustrative but non-limiting example of an epoxy-silane pretreated silica filler is Millisil W12 EST, commercially available from Quarzwerke Group. An illustrative but non-limiting example of an epoxy-silane pretreated wollastonite filler is Tremin 283-100 EST, commercially available from Quarzwerke Group.

[0071] In at least one embodiment, the filler is selected from the group consisting of silica, wollastonite, quartz, alumina, aluminum nitride, boron nitride, silicon nitride, silicon carbide, beryllium oxide, epoxy-silane pretreated silica, epoxy-silane pretreated wollastonite, and combinations thereof.

[0072] The filler can have various particle sizes. In some embodiments, the filler can have a D50 particle size of, for example, about 1 μm to about 100 μm, such as about 35 μm or larger, or about 15 μm to about 30 μm, or about 1 μm to about 4 μm. In at least one embodiment, the D50 particle size of the filler can be in the range of about 35 μm to 80 μm, such as about 40 μm to about 70 μm, such as about 45 μm to about 60 μm. Additionally or alternatively, the D50 particle size of the filler can be in the range of about 15 μm to about 25 μm, such as about 15 μm to about 20 μm or about 20 μm to about 25 μm. Additionally or alternatively, the D50 particle size of the filler can be in the range of about 1 μm to about 3 μm, such as about 1 μm to about 2 μm or about 2 μm to about 3 μm. Other D50 particle sizes are contemplated. The D50 particle size is the particle size (median particle size) at which the particle size distribution based on mass accumulates 50%, meaning the particle size at the point where the cumulative value becomes 50% in the cumulative curve in which the particle size distribution is obtained based on mass and the entire mass is set to 100%. The D50 particle size can be measured by laser diffraction. Laser diffraction can be performed using a MASTERSIZER 3000 instrument from Marvern Inc. using ethanol as a solvent based on the ISO-13320 standard. The incident laser is scattered by the particles dispersed in the solvent, and the intensity and direction values ​​of the scattered laser vary according to the size of the particles analyzed using the Mie theory. Through the above analysis, the particle size can be evaluated by obtaining the distribution by converting into the diameter of a sphere having the same volume as the dispersed particles and thereby obtaining the D50 value as the median value of the distribution.

[0073] The filler may have any suitable shape. The filler shape may be selected based on, for example, insulation properties, filling effect, dispersibility, viscosity of the resin composition, thixotropy of the resin composition, sedimentation potential in the composition, desired heat resistance, desired thermal conductivity, combinations thereof, and other factors. The filler shape includes spherical fillers, substantially spherical fillers, non-spherical fillers (e.g., needle-shaped, plate-shaped, etc.), or combinations thereof.

[0074] Combinations or blends of fillers in any suitable proportions can be used in the compositions described herein. Such combinations can include more than one type of filler (e.g., silica and epoxysilane pretreated silica), more than one size of filler (e.g., silicon carbide having a D50 particle size of about 1.5 μm to about 4 μm and carbide having a D50 particle size of about 20 μm to about 35 μm), more than one shape (e.g., spherical and acicular), or combinations thereof.

[0075] The total amount of filler in the composition described herein can be about 30wt% to about 80wt%, such as about 30wt% to about 70wt%, such as about 40wt% to about 60wt%, such as about 45wt% to about 55wt% based on the total wt% of the composition. Other amounts are considered. In some embodiments, the total amount (wt%) of filler in the composition described herein can be 30, 35, 40, 45, 50, 55, 60, 65, 70, 75 or 80, or ranges thereof, based on the wt% of the composition. Each of the aforementioned numbers can be preceded by the words "about", "at least about", "less than about" or "greater than about", and any of the aforementioned numbers can be used alone to describe an open range or used in combination to describe a closed range.

[0076] The weight ratio of the total amount of epoxy resin to the total amount of filler in the composition described herein may be any suitable ratio or range. In some examples, the weight ratio of the total amount of epoxy resin to the total amount of filler in the composition described herein may be from about 1:10 to about 10:1, such as from about 1:8 to about 8:1, such as from about 1:5 to about 5:1, such as from about 1:3 to about 3:1, such as from about 1:2.5 to about 2.5:1, such as from about 1:2 to about 2:1, such as from about 1:1.5 to about 1.5:1. In at least one embodiment, the weight ratio of the total amount of epoxy resin to the total amount of filler in the composition described herein may be 1:10, 1:9.5, 1:9, 1:8.5, 1:8, 1:7.5, 1:7, 1:6.5, 1:6, 1:5.5, 1:5, 1:4.5, 1:4, 1:3.9, 1:3.8, 1:3.7, 1:3.6, 1:3.5 , 1:3.4, 1:3.3, 1:3.2, 1:3.1, 1:3, 1:2.9, 1:2.8, 1:2.7, 1:2.6, 1:2.5, 1:2.4, 1:2.3, 1:2.2, 1:2.1, 1:2, 1:1.9, 1:1.8, 1:1.7, 1:1.6, 1:1.5, 1:1.4, 1:1.3, 1:1 .2, 1:1.1, 1:1, 1.1:1, 1.2:1, 1.3:1, 1.4:1, 1.5:1, 1.6:1, 1.7:1, 1.8:1, 1.9:1, 2:1, 2.1:1, 2.2:1, 2.3:1, 2.4:1, 2.5:1, 2.6:1, 2.7:1, 2.8:1, 2.9:1, 3:1, 3. 1 :1, 3.2:1, 3.3:1, 3.4:1, 3.5:1, 3.6:1, 3.7:1, 3.8:1, 3.9:1, 4:1, 4.5:1, 5:1, 5.5:1, 6:1, 6.5:1, 7:1, 7.5:1, 8:1, 8.5:1, 9:1, 9.5:1 or 10:1, or ranges thereof, although other weight ratios are contemplated.

[0077] In addition to the epoxy resin, latent catalytic curing agent, and filler, the compositions described herein may also optionally include additives. Illustrative but non-limiting examples of optional additives may include or be selected from the group consisting of modifiers (such as alcohols or polyols), block copolymers, defoamers, anti-settling agents, air release agents, pigments, ultraviolet stabilizers (UV stabilizers), or combinations thereof. These additives may be used to aid processing, improve fracture toughness, and for other purposes.

[0078] In some embodiments, the total amount of additives in the compositions described herein can be from about 0 wt % to about 10 wt %, such as from about 0.01 wt % to about 10 wt %, such as from about 0.1 wt % to about 9 wt %, such as from about 0.5 wt % to about 7 wt %, such as from about 1 wt % to about 5 wt %, such as from about 2 wt % to about 3 wt %. Other amounts are contemplated.

[0079] Suitable modifiers for constituents include alcohols (also known as monohydric alcohols), polyols (also known as polyols) or combinations thereof. Suitable polyols include, but are not limited to, glycols (glycols (diols)) derived from ethylene glycol, such as ethylene glycol, propylene glycol, methyl glycol, propylene glycol, neopentyl glycol, diethylene glycol, triethylene glycol, polyethylene glycol, polypropylene glycol, sugar compounds or their constituents. Trivalent or higher valence alcohols can also be used, such as glycerol, trimethylolpropane, glucose, other sugar compounds or their combinations. Other alcohols and polyols are contemplated. In some instances, constituents as described herein include polyols, such as glycols, such as ethylene glycol, propylene glycol, polyethylene glycol, polypropylene glycol, glycerol, sugar compounds or their combinations. Non-limiting examples of glycols can include Heloxy PF, which is a propylene glycol with a weight average molecular weight (Mw) of 400 g / mol. In at least one embodiment, constituents as described herein can include a modifier, wherein the modifier is a polyol.

[0080] In some embodiments, the total amount of modifier in the composition described herein can be from about 0 wt % to about 10 wt %, such as from about 0.05 wt % to about 8 wt %, such as from about 0.05 wt % to about 2 wt %. In at least one embodiment, the total amount of modifier in the composition (in wt %) can be 0, 0.01, 0.03, 0.05, 0.1, 0.25, 0.5, 0.75, 1, 1.5, 2, 2.5, 3, 3.5, 4, 4.5, 5, 5.5, 6, 6.5, 7, 7.5, 8, 8.5, 9, 9.5 or 10, or ranges thereof, although other amounts are also contemplated. Each of the aforementioned numbers can be preceded by the words "about," "at least about," "less than about," or "greater than about," and any of the aforementioned numbers can be used alone to describe an open range or in combination to describe a closed range.

[0081] Suitable block copolymers include functionalized polysiloxanes, polysiloxane-containing block copolymers, and combinations thereof. For example, block copolymers having polysiloxane and an organic block (e.g., based on caprolactone or other lactones) such as Genioperl W35 (Wacker Chemie AG, Munich, Germany) can be used. Block copolymers can be used to improve fracture toughness.

[0082] Illustrative but non-limiting examples of defoaming agents may include FC-402 (which includes tall oil fatty acid, glycol, and a silicon-containing material, and is commercially available from Enterprise Specialty Products); Byk-037 (a volatile-free, silicone-containing defoaming agent commercially available from BYK-Chemie GmbH); Surfynol 104H (a multifunctional surfactant commercially available from Evonik Industries AG), or combinations thereof.

[0083] In some embodiments, the total amount of defoaming agent in the composition described herein can be from about 0 wt % to about 10 wt %, such as from about 0.05 wt % to about 8 wt %, such as from about 0.05 wt % to about 2 wt %, based on the total wt % of the composition. In at least one embodiment, the total amount of defoaming agent in the composition (in wt %) can be 0, 0.01, 0.03, 0.05, 0.1, 0.25, 0.5, 0.75, 1, 1.5, 2, 2.5, 3, 3.5, 4, 4.5, 5, 5.5, 6, 6.5, 7, 7.5, 8, 8.5, 9, 9.5 or 10, or ranges thereof, based on the total wt % of the composition, although other amounts are also contemplated. Each of the aforementioned numbers can be preceded by the words "about," "at least about," "less than about," or "greater than about," and any of the aforementioned numbers can be used alone to describe an open range or in combination to describe a closed range.

[0084] Anti-settling agents can reduce the settling behavior of various components in the composition. Illustrative but non-limiting examples of anti-settling agents include Byk 430, Byk 410, Byk 411, Byk 431, each of which is commercially available from BYK-Chemie GmbH. Combinations of anti-settling agents can be used. In some embodiments, the total amount of anti-settling agent in the composition described herein can be from about 0 wt % to about 10 wt %, such as from about 0.05 wt % to about 8 wt %, such as from about 0.05 wt % to about 2 wt %, based on the total wt % of the composition. In at least one embodiment, the total amount of defoaming agent in the composition (in wt %) can be 0, 0.01, 0.03, 0.05, 0.1, 0.25, 0.5, 0.75, 1, 1.5, 2, 2.5, 3, 3.5, 4, 4.5, 5, 5.5, 6, 6.5, 7, 7.5, 8, 8.5, 9, 9.5, or 10, or ranges thereof, based on the total wt % of the composition, although other amounts are also contemplated. Each of the foregoing numbers can be preceded by the words "about," "at least about," "less than about," or "greater than about," and any of the foregoing numbers can be used alone to describe an open range or in combination to describe a closed range.

[0085] Air release agents can reduce the amount of foaming in the composition (e.g., to remove gaseous impurities). Illustrative but non-limiting examples of air release agents include Byk S732, Byk-A 500, Byk-A 50, Byk-A 515, Byk 390, Byk 306, Byk 315, and Byk 356, each of which is commercially available from BYK-Chemie GmbH. Combinations of anti-settling agents can be used.

[0086] Illustrative, but non-limiting, examples of pigments can include magnesium oxide (commercially available from Sigma Aldrich), iron oxides in various oxidation states (commercially available from Lanxess AG), titanium oxide (commercially available from Sigma Aldrich), aluminum oxide (commercially available from Sigma Aldrich), titanium dioxide (such as Ti-Pure 901 / 900 commercially available from Chemours), or combinations thereof. Combinations of pigments can be used. In some embodiments, the total amount of pigment in the compositions described herein can be from about 0 wt % to about 10 wt %, such as from about 0.05 wt % to about 8 wt %, such as from about 0.05 wt % to about 2 wt %, based on the total wt % of the composition. In at least one embodiment, the total amount of pigment in the composition (in wt %) can be 0, 0.01, 0.03, 0.05, 0.1, 0.25, 0.5, 0.75, 1, 1.5, 2, 2.5, 3, 3.5, 4, 4.5, 5, 5.5, 6, 6.5, 7, 7.5, 8, 8.5, 9, 9.5, or 10, or ranges thereof, based on the total wt % of the composition, although other amounts are also contemplated. Each of the foregoing numbers can be preceded by the words "about," "at least about," "less than about," or "greater than about," and any of the foregoing numbers can be used alone to describe an open range or in combination to describe a closed range.

[0087] In some embodiments, the compositions described herein may further comprise an additive selected from the group consisting of a modifier, a block copolymer comprising functionalized polysilicone, a block copolymer containing polysilicone, a defoamer, an anti-settling agent, an air release agent, a pigment, an ultraviolet stabilizer (UV stabilizer), and combinations thereof. In these and other embodiments, the amount of the additive in the compositions described herein may be greater than 0 wt % and less than about 10 wt % based on the total wt % of the curable composition.

[0088] In at least one embodiment, the composition described herein may include: based on the total weight of the composition, about 20 wt% to about 70 wt% of an aromatic epoxy resin; based on the total weight of the composition, about 30 wt% to about 80 wt% of a filler; and greater than 0 wt% and less than about 10 wt% of a latent catalytic curing agent, the total weight of the composition not exceeding 100 wt%. In some embodiments, the composition described herein may further include a polyol, such as a polyol selected from the group consisting of ethylene glycol, propylene glycol, polyethylene glycol, polypropylene glycol, glycerol, a sugar compound, and combinations thereof. In at least one embodiment, the latent catalytic curing agent that can be used with the composition described herein is a latent catalytic curing agent that is active at a temperature of about 30°C to about 300°C, such as about 50°C to about 275°C.

[0089] As described herein, the composition is stable under ambient conditions or conditions other than ambient conditions due to, for example, the use of a latent catalytic curing agent. In contrast, conventional compositions for thermal management are typically two-component systems in which the resin component and the curing agent component must be mixed on-site immediately prior to use.

[0090] Under ambient conditions, such as room temperature (about 20° C. to about 25° C.), the compositions described herein can be in the form of a fluid, paste, or viscous mass. If the composition is curable, there is no limitation on the method that can be used to cure the composition.

[0091] method

[0092] The embodiments described herein also generally relate to methods of making or forming compositions. Conventional compositions for thermal management are typically manufactured using a two-component system (e.g., a resin component and a curing agent component), wherein the composition is formed upon mixing the two components. After mixing, the mixture is neatly poured into a preheated mold.

[0093] In contrast, the compositions described herein can be one-component systems. The compositions are heated prior to pouring and then injected into a mold for pouring. Unlike conventional compositions, the compositions described herein can include a latent catalytic curing agent that does not polymerize the epoxy resin until a stimulus is applied.

[0094] Generally speaking, the composition described herein can be manufactured or formed by introducing the materials of the composition (epoxy resin, catalytic curing agent, filler, and optional additives) into each other and mixing the materials.

[0095] The epoxy resin, latent catalytic curing agent, filler, and optional additives may be placed in a container and stirred, mixed, or otherwise agitated under mixing conditions effective to form the composition. The mixing conditions may include using a mixing pressure of about 10 mbar (-1,000 Pa) to about 1,000 mbar (100,000 Pa), such as about 20 mbar (-2,000 Pa) to about 500 mbar (-50,000 Pa), such as about 30 mbar (3,000 Pa) to about 150 mbar (-15,000 Pa), such as about 40 mbar (-4,000 Pa) to about 70 mbar (-7,000 Pa), such as about 50 mbar (-5,000 Pa), although other pressures are also contemplated. In some examples, the mixing conditions may include a mixing pressure (in Pa) of about 1,000, 2,000, 3,000, 4,000, 5,000, 6,000, 7,000, 8,000, 9,000, or 10,000, or a range thereof, although other pressures are also contemplated. Each of the aforementioned numbers may be preceded by the words "about," "at least about," "less than about," or "greater than about," and any of the aforementioned numbers may be used alone to describe an open-ended range or in combination to describe a closed range.

[0096] If desired, mixing conditions can include elevated temperatures. However, if elevated temperatures are used during mixing of the materials, the mixing temperature should be below the temperature at which the latent catalytic curing agent becomes active.

[0097] Mixing conditions can include stirring, mixing, agitating or a combination thereof by using a suitable device, such as a mechanical stirrer. Such mixing conditions can include using a suitable device, such as a mechanical stirrer (e.g., an overhead stirrer), a magnetic stirrer (e.g., a magnetic stirring bar in a container is placed above the magnetic stirrer) or other suitable devices. For example, a stirrer (having blades or propellers) can be rotated by receiving the rotational power from a stirring motor, thereby stirring one or more materials at a suitable rotational speed. Mixing conditions can include utilizing a non-reactive gas, such as N2, Ar or a combination thereof. For example, a non-reactive gas can be introduced into one or more of an epoxy resin, a catalytic curing agent, a filler and optionally an additive to degas various components or otherwise remove unwanted gas (e.g., oxygen) from the mixture.

[0098] Mixing conditions can include using suitable device, such as mechanical stirrer, magnetic stirrer or other suitable devices, as described above.For example, agitator (having blade or propeller) can be rotated by receiving the rotational power from stirring motor, thereby stirs one or more materials with suitable rotational speed, such as approximately 50 revs / min (rpm) to approximately 1,500rpm, such as approximately 75rpm to approximately 1,000rpm, such as approximately 100rpm to approximately 900rpm, such as approximately 200rpm to approximately 800rpm, such as approximately 300rpm to approximately 700rpm, such as approximately 400rpm to approximately 600rpm, such as approximately 450rpm to approximately 550rpm, such as approximately 500rpm.Any aforementioned numeral can be used alone to describe open range or be used in combination to describe closed range.Other rotational speeds can be considered and other rotational speeds can be selected based on the ability of fully mixing component. The mixing conditions may include mixing for any suitable period of time, such as from about 1 min to about 48 h, such as from about 5 min to about 24 h, such as from about 30 min to about 10 h, such as from about 1 h to about 5 h, such as from about 2 h to about 3 h, although other periods may be considered. Any of the aforementioned numbers may be used alone to describe an open range or in combination to describe a closed range.

[0099] At this stage, a composition is formed and can be stored for immediate use, later use, or a combination thereof. Additionally, at this stage, the composition can be a curable composition such that the composition can be cured by applying a stimulus. The curable composition can be in the form of a liquid, paste, or gel. One or more materials of the curable composition can be dispersed or suspended as particles.

[0100] In some embodiments, the compositions described herein may be curable compositions. The curable compositions may be 1K systems.

[0101] A stimulus, such as heat, acts on a material (e.g., a latent catalytic curing agent) in the composition. Upon application of the stimulus, the latent catalytic curing agent causes a polyaddition reaction to occur, resulting in coupling, crosslinking, or both of the epoxy resin and the other material. The composition also hardens.

[0102] The composition can be cured under conditions that effectively cure the composition. As mentioned above, the latent catalytic curing agent present in the composition reacts to a temperature higher than ambient temperature and becomes active. The selected curing conditions depend on the temperature at which, for example, the latent catalytic curing agent causes a reaction to occur, which results in coupling, crosslinking, or both of epoxy resin and other materials. Such curing conditions may include heating the composition to a temperature higher than ambient temperature, such as from about 30°C to about 300°C, such as from about 40°C to about 285°C, such as from about 50°C to about 275°C, such as from about 75°C to about 250°C, such as from about 100°C to about 225°C, such as from about 125°C to about 200°C, such as from about 150°C to about 175°C, although other temperatures may be considered. Any of the aforementioned numbers may be used alone to describe an open range or in combination to describe a closed range.

[0103] Curing conditions may include curing for any suitable amount of time, such as from about 1 min to about 48 h, such as from about 5 min to about 24 h, such as from about 30 min to about 10 h, such as from about 1 h to about 5 h, such as from about 2 h to about 3 h, although other time periods may be considered. Any of the aforementioned numbers may be used alone to describe an open range or in combination to describe a closed range. Curing may be performed in stages, such as a curing cycle. For example, a curing cycle may include curing a composition at a first temperature for a first time; raising the temperature to a second temperature at a selected heating rate; and curing the composition at a second temperature for a second time. As a non-limiting example, a curing cycle may have the following profile: curing the composition at about 100 ° C for about 2 hours, raising the temperature to about 190 ° C (at a rate of about 1 ° C / min to about 10 ° C / min); and then curing the composition at about 190 ° C for about 3 hours. Other curing or curing cycles are contemplated.

[0104] If necessary, can before solidifying, constituent is introduced into mould.That is, curable composition can be shaped (for example, moulded) into any suitable shape.According to the application of constituent to be used, the mixture produced can be carried out corresponding shaping.Then can solidify in selected temperature or temperature range, and this depends on the temperature that employed latent catalytic curing agent becomes active.Then can solidify composition be placed on heating device, heating equipment or its assembly.

[0105] In some embodiments, the composition may include a reaction product of a mixture comprising an epoxy resin, a catalytic curing agent, a filler, and optionally, additives.

[0106] The compositions of the present disclosure have excellent thermal conductivity. In some embodiments, the thermal conductivity of the composition can be about 0.4 W / mK or higher, about 5.0 W / mK or lower, or a combination thereof. In some examples, the thermal conductivity of the composition can be about 0.5 W / mK to about 3.0 W / mK, such as about 0.5 W / mK to about 2.0 W / mK, such as about 1.0 W / mK to about 1.5 W / mK. In at least one embodiment, the compositions described herein may have a thermal conductivity of 0.4, 0.5, 0.6, 0.7, 0.8, 0.9, 1.0, 1.1, 1.2, 1.3, 1.4, 1.5, 1.6, 1.7, 1.8, 1.9, 2.0, 2.1, 2.2, 2.3, 2.4, 2.5, 2.6, 2.7, 2.8, 2.9, 3.0, 3.1, 3.2, 3.3, 3.4, 3.5, 3.6, 3.7, 3.8, 3.9, 4.0, 4.1, 4.2, 4.3, 4.4, 4.5, 4.6, 4.7, 4.8, 4.9 or 5.0, or ranges thereof, although other thermal conductivities are contemplated. Each of the aforementioned numbers may be preceded by the word "about," "at least about," "less than about," or "greater than about," and any of the aforementioned numbers may be used alone to describe an open range or in combination to describe a closed range.

[0107] use

[0108] The embodiments of the present disclosure are also generally related to the use of the compositions described herein. The compositions described herein can be used for thermal management of various equipment, devices, or components thereof. In general, the compositions can be used together with heat-generating components such as electrical or electronic equipment, electrical or electronic equipment devices, or components thereof. For example, the cured composition (or cured product) can directly or indirectly contact electrical or electronic parts. Because the cured composition is heat-conductive, the cured composition can remove the heat generated by the electrical or electronic parts. The cured composition can be placed on, encapsulate, or otherwise cover at least a portion of an equipment, device, or component thereof.

[0109] Illustrative but non-limiting examples of heat-generating components (e.g., electrical / electronic equipment and electrical / electronic devices) include electric motors, generators, electric drives for e-mobility, or components thereof. E-mobility generally refers to electric drive technology used in applications such as electric cars, electric bicycles, electric scooters, electric buses, electric trucks, and others, or components thereof. Other devices and equipment include batteries, televisions, videos, computers, medical equipment, office machines, or communications devices, or devices / equipment that generate heat, or components thereof.

[0110] Embodiments of the present disclosure also generally relate to articles comprising the compositions described herein. In some embodiments, an article comprises a heat generating component and a composition disposed above (or on) the heat generating component. The composition disposed above (or on) the heat generating component can be any suitable composition described herein. The composition can be a cured composition (or cured product) that can directly or indirectly contact the heat generating component.

[0111] The heat generating component may be any suitable component that generates heat or thermal energy. Examples of heat generating components may include electronic devices, electrical devices, electronic devices, electrical equipment, components thereof, or combinations thereof, such as those described herein. For example, by contacting the heat generating component with a thermally conductive composition described herein (directly or indirectly), the thermally conductive composition may transfer or transmit thermal energy or heat from the heat generating component to another element or itself. Therefore, in some embodiments, the composition can be used to keep temperature-sensitive components in or around electronic / electrical articles within a specified operating temperature to avoid failure. In at least one embodiment, the article includes: a heat generating component; and a composition described herein, which is disposed on the heat generating component.

[0112] In some embodiments, the article includes a heating component and a heat dissipation component disposed on (or above) the surface of the heating component. The heating component may be or include a heating member. The heat dissipation component may be or include a composition as described herein. The composition may be a cured composition (or cured product). The heat dissipation component may directly or indirectly contact the heating component. The heat dissipation component may transfer or transmit thermal energy (or heat) from the heating component to another component or itself. The heat dissipation component can be used to keep temperature-sensitive components in or around electronic / electrical items within a specified operating temperature to avoid malfunctions.

[0113] In some embodiments, the heat generating component comprises a component of an electric motor, a component of a generator, a component of an electric drive, a component of a battery, a component of a television, a component of a computer, a component of a medical device, a component of an office machine, a component of a communication device, or combinations thereof, among others.

[0114] If desired, the compositions described herein can be used in other applications, such as in the coating or adhesive industry. Such compositions can generally be used to produce composites, adhesives, insulation materials, molded products, adhesives, paints, sealants, laminates, and other articles and products.

[0115] In some embodiments, the articles described herein can be manufactured by a suitable method. In at least one embodiment, a method of forming an article comprises: placing a curable composition comprising an aromatic epoxy resin, a latent catalytic curing agent, and a filler in a mold; heating the mold and the curable composition to form a cured composition; and placing the cured composition on a heat generating assembly to form the article. In some embodiments, heating the mold and the curable composition is performed at a temperature of about 100° C. to about 225° C., although other temperatures are contemplated.

[0116] The following examples are provided so as to provide those of ordinary skill in the art with a complete disclosure and description of how to make and use the embodiments of the present disclosure, and are not intended to limit the scope of the embodiments of the present disclosure. Efforts have been made to ensure accuracy of the numbers used, but some experimental errors and deviations should be accounted for.

[0117] Examples

[0118] Test Method

[0119] The thermal conductivity of the composition is measured according to ASTM E 1461.

[0120] Instance composition

[0121] The Example and Comparative Example compositions were prepared using the components shown in Table 1. Unless otherwise indicated, the amounts shown in Table 1 are in weight percent. The thermal conductivity of the compositions is also shown in Table 1. In Table 1, "C.Ex." refers to a Comparative Example, and "Ex." refers to an Example of the present disclosure. The Example composition is a catalytically cured epoxy resin (using a latent catalytic curing agent). In contrast, the Comparative Example composition utilizes the curing agent as part of a two-component system (resin component and curing agent component) that requires on-site mixing.

[0122] Epikote 828LVEL is a difunctional bisphenol-A-diglycidyl-ether epoxy resin; Epikote 162 is a bisphenol-F-diglycidyl-ether epoxy resin; Epikote 158 is a bisphenol-F-diglycidyl-ether epoxy resin; Epikote 496 is a tetraglycidyl-methylene-diphenylamine epoxy resin; and Epikote 1031 is an epoxidized tetraphenylethane epoxy resin, each of which is commercially available from Westlake Epoxy. Epikote 828LVEL, Epikote 162, Epikote 158, Epikote 496, and Epikote 1031 are used as epoxy resins.

[0123] Polypropylene glycol (400 g / mol), commercially available from Hexion Inc. under the trade name Heloxy, was used as a modifier. Boron trichloride dimethyloctylamine complex and 1-methylimidazole were used as catalysts, both commercially available from Hexion Inc. Fillers included Millisil W12 EST, commercially available from Quarzwerke Group, Tremin 283-100 EST, commercially available from Quarzwerke Group, and SiC, commercially available from ESD-SIC.

[0124] The comparative example includes a curing agent component. This curing agent component includes: methyl nadic anhydride (also known as methyl-5-norbornene-2,3-dicarboxylic anhydride; CAS No. 25134-21-8), commercially available from Polynt; DBU is 1,8-diazabicyclo[5.4.0]undec-7-ene (CAS No. 6674-22-2), commercially available from BASF; additives include an air release agent (polysiloxane) and an anti-settling agent (urea-modified, medium-polarity polyamide); and Genioperl W35 (modifier) ​​commercially available from Wacker Chemie.

[0125] The example composition is manufactured according to the following non-limiting procedures. Before the admixture of materials, the resin and filler are heated at a temperature of about 70°C for about 2 hours. After removing the heat (making the latent catalytic curing agent unreacted), the resin, filler and latent catalytic curing agent are then placed in a container and mixed at a pressure of about 50mbar (~5,000Pa) with about 500 revolutions per minute (rpm) to about 1,000rpm. The composition is delivered to a separate mold and cured in the mold using a time and temperature profile that results in complete curing or sufficient curing to release the cured composition from the mold after the curing cycle. In these examples, the following curing profile is used: keep at about 100°C for about 2 hours, heat to about 190°C and cure at about 190°C for about 3 hours. The cured composition is cooled to room temperature. The cured composition is then taken out of the mold.

[0126] Table 1

[0127]

[0128]

[0129]

[0130] The thermal conductivity data in Table 1 indicate that the example compositions have enhanced thermal conductivity—approximately 10% to approximately 15%—relative to the comparative compositions. For example, Comparative Example 1, which includes EP828LVEL and wollastonite filler, has a thermal conductivity of approximately 0.54 W / mK, while Example 1, which includes approximately 25% EP162, 75% Ep158, and the same amount of wollastonite filler, has a higher thermal conductivity of approximately 0.61 W / mK. Although Examples 2, 3, and Comparative Example 2 include the same Millisil filler (approximately 72%), the thermal conductivity of Example 2a (approximately 0.96 W / mK) and Example 2b (approximately 1.02 W / mK) is significantly improved relative to Comparative Example 2 (0.84 W / mK). Similarly, although Example 3 and Comparative Example 3 include the same Millisil filler (approximately 69%), the thermal conductivity of Example 3 (approximately 0.91 W / mK) is significantly improved relative to Comparative Example 3 (0.8 W / mK). In addition, although Example 4 and Comparative Example 4 include the same silicon carbide filler, Example 4 (about 0.57W / mK) has a thermal conductivity enhanced relative to Comparative Example 4 (0.51W / mK). Although not wishing to be bound by theory, it is believed that the higher aromatic content of the example composition causes a significant improvement in thermal conductivity. For example, although each of the comparative examples is diluted with a curing agent component, the example composition of the present disclosure is not diluted with a curing agent component. This lack of dilution causes the example composition to have a relatively high aromatic content compared to the comparative example. In addition, and unlike the comparative example containing anhydride curing agent (methyl nadic anhydride), the examples of the present disclosure do not contain anhydride. Anhydride is a cause of concern due to its respiratory sensitization effect.

[0131] The thermal conductivity data also demonstrates that the compositions of the present disclosure can be used for thermal management of heat-generating components, such as transferring or transmitting thermal energy or heat from a heat-generating component to a different component or to itself. For example, the compositions of the present disclosure can be used with heat-generating devices, heat-generating equipment, components thereof, or combinations thereof. By contacting the compositions described herein with heat-generating devices, heat-generating equipment, or components thereof (directly or indirectly), the compositions can be used to maintain temperature-sensitive components within specified operating temperatures to prevent malfunctions.

[0132] The examples also demonstrate that the compositions described herein can be one-component systems (1K systems) because polymerization does not occur until a stimulus such as heat is applied (e.g., a curing profile). The compositions of the present disclosure can also be stored at ambient temperature. In contrast, comparative compositions used for thermal management are 2K systems that require on-site mixing.

[0133] Unlike conventional compositions for thermal management, which are typically 2K systems that require on-site mixing, the embodiments described herein can be one-component systems because polymerization does not occur until a stimulus (such as heat) is applied. For example, the compositions of the present disclosure can include an epoxy resin, a catalytic curing agent, a filler, and optionally, additives. Upon application of a stimulus (such as heat), the latent catalytic curing agent can cause, for example, a polyaddition reaction to occur, resulting in coupling, crosslinking, or both of the epoxy resin and the other material. Such compositions can be curable compositions that can be stored under ambient conditions. Conventional compositions for thermal management lack such capabilities because they are not one-component systems.

[0134] Here, the use of the thermally conductive compositions described herein can significantly improve the efficiency of state-of-the-art electrical and electronic devices relative to conventional technology. This is because the compositions of the present disclosure exhibit improved thermal conductivity (i.e., improved heat dissipation of heat-generating components), which in turn can better reduce the operating temperature of such electrical and electronic devices. Consequently, the reduced operating temperature achieved by the compositions of the present disclosure allows for increased power output relative to conventional heat dissipation technologies.

[0135] In general, the thermal conductivity data of the example compositions indicate that the compositions of the present disclosure can provide lower operating temperatures when used with electrical equipment relative to conventional compositions. This beneficial lower operating temperature can result in reduced electrical losses in electrical equipment and reduce thermal aging of electrical equipment. This is especially true for electric drives for e-mobility, as electric drives for e-mobility typically operate at the highest temperatures of e-mobility devices. As mentioned above, e-mobility generally refers to electric drive technology used in applications such as electric cars, electric bicycles, electric scooters, electric buses, electric trucks, and others. In addition, the compositions described herein may not contain anhydrides as curing agents. Anhydrides have raised concerns due to their respiratory sensitization effects.

[0136] Embodiments of the present disclosure generally relate to epoxy resin compositions, methods for making epoxy resin compositions, and uses of epoxy resin compositions. The embodiments described herein can be used to dissipate heat in self-heating devices, heat-generating equipment, or components thereof, such as electrical and electronic devices, electrical and electronic devices, or components thereof. These compositions can be curable compositions that can be stored under ambient conditions.

[0137] As used herein, reference to an R group, an alkyl group, a substituted alkyl group, a hydrocarbyl group, or a substituted hydrocarbyl group without specifying a specific isomer (such as butyl) explicitly discloses all isomers (such as n-butyl, isobutyl, secondary butyl, and tertiary butyl). For example, reference to an R group having 4 carbon atoms explicitly discloses all isomers thereof. When a compound is described herein without specifying a specific isomer, enantiomer, or diastereomer of the compound, such as in a formula or chemical name, the description is intended to include each isomer and enantiomer of the compound described, alone or in any combination.

[0138] It will be apparent from the foregoing general description and specific aspects that, although the forms of various aspects have been illustrated and described, various modifications may be made without departing from the spirit and scope of the present disclosure. Therefore, the present disclosure is not intended to be limited in this manner. Similarly, the term "comprising" is considered to be synonymous with the term "including". Similarly, whenever a composition, an element, a group of elements or a method is preceded by the transition phrase "comprising", it should be understood that we also consider the same composition, method or element group having the transition phrase "essentially consisting of", "consisting of", "selected from a group consisting of" or "being" before the description of the composition, element, multiple elements or method, and vice versa, such as the terms "comprising", "essentially consisting of", "consisting of" also include the product of the combination of elements listed after the term.

[0139] For the purposes of this disclosure, and unless otherwise specified, all numerical values ​​in the embodiments and claims herein are modified by "about" or "approximately" indicated values, and take into account the experimental errors and variations expected by those skilled in the art. For the sake of brevity, only certain ranges are explicitly disclosed herein. However, the range of any lower limit can be combined with any upper limit to list a range that is not explicitly listed, and the range of any lower limit can be combined with any other lower limit to list a range that is not explicitly listed, in this way, the range of any upper limit can be combined with any other upper limit to list a range that is not explicitly listed. For example, the enumeration of a numerical range of 1 to 5 includes subranges of 1 to 4, 1.5 to 4.5, 1 to 2 and other subranges. As another example, the enumeration of a numerical range of 1 to 5 (such as 2 to 4) includes subranges of 1 to 4 and other subranges such as 2 to 5. In addition, each point or individual value between its endpoints is included in the range, even if not explicitly listed. For example, the narration of a numerical range of 1 to 5 includes the numbers 1, 1.5, 2, 2.75, 3, 3.80, 4, 5 and other numbers. Thus, each point or individual value can be combined with any other point or individual value or any other lower or upper limit as its own lower limit or upper limit to recite a range not explicitly recited.

[0140] As used herein, the indefinite article "a" or "an" shall mean "at least one," unless specified to the contrary or the context clearly indicates otherwise. For example, aspects comprising "a filler" include aspects comprising one, two, or more fillers, unless specified to the contrary or the context clearly indicates that only one filler is included.

[0141] While the foregoing is directed to various aspects of the disclosure, other and further aspects of the disclosure may be devised without departing from the basic scope thereof, the scope of which is determined by the claims that follow.

Claims

1. An article, comprising: heat generating components; and A composition, the composition being disposed on the heat-generating component, the composition comprising: Aromatic epoxy resins; a latent catalytic curing agent, the latent catalytic curing agent being active at a temperature of about 30° C. to about 300° C.; and filler.

2. The article of claim 1, wherein: The aromatic epoxy resin has an aromatic content of about 30 wt % to about 70 wt % based on the total weight % of the aromatic epoxy resin; The aromatic epoxy resin is selected from the group consisting of difunctional bisphenol-A-diepoxypropyl-ether, bisphenol-F-diepoxypropyl-ether, tetraepoxypropyl-methylene-diphenylamine, epoxidized tetraphenylethane, derivatives thereof, and combinations thereof; or Its combination.

3. The article of claim 1, wherein: The latent catalytic curing agent is selected from the group consisting of imidazole, substituted imidazole, imidazole adduct, imidazole complex, tertiary amine, oligomeric polyethylene piperazine, quaternary ammonium compound, quaternary phosphonium compound, urea derivative, boron trifluoride complex, boron trichloride complex, epoxy addition reaction product, tetraphenylene-boron complex, boron amine, titanate amine, acetylacetonate metal salt, naphthenate metal salt, octoate metal salt, other metal salts, metal chelate and combinations thereof.

4. The article of claim 1, wherein the latent catalytic curing agent is selected from the group consisting of a sulfonium salt of formula (I), a sulfonium salt of formula (II), a sulfonium salt of formula (III), a sulfonium salt of formula (IV), and combinations thereof: in, In formulas (I)-(IV): Each R group is independently C1-C12 alkyl, C3-C8 cycloalkyl, C4-C10 cycloalkylalkyl, or phenyl, which is unsubstituted or mono- or polysubstituted by C1-C8 alkyl, C1-C4 alkoxy, halogen, hydroxy, nitro, phenyl, phenoxy, alkoxycarbonyl having 1 to 4 carbon atoms, or acyl having 1 to 12 carbon atoms; Ar, Ar 1 or Ar 2 Each of the groups is independently phenyl, naphthyl or fluorenyl, wherein the phenyl, naphthyl or fluorenyl group is unsubstituted or mono- or polysubstituted by C1-C8 alkyl, C1-C4 alkoxy, halogen, hydroxy, nitro, phenyl, phenoxy, alkoxycarbonyl having 1 to 4 carbon atoms or acyl having 1 to 12 carbon atoms; Each arylene group is independently phenylene, naphthylene, or fluorene, wherein the phenylene, naphthylene, or fluorene group is unsubstituted or mono- or polysubstituted by C1-C8 alkyl, C1-C4 alkoxy, halogen, hydroxy, nitro, phenyl, phenoxy, alkoxycarbonyl having 1 to 4 carbon atoms, or acyl having 1 to 12 carbon atoms; and Each Q - Independently SbF6 - 、AsF6 - or SbF5OH - .

5. The article of claim 1, wherein the composition comprises: about 20 wt % to about 70 wt % of the aromatic epoxy resin, based on the total wt % of the composition; about 30 wt % to about 80 wt % of the filler, based on the total wt % of the composition; and The latent catalytic curing agent is greater than 0 wt % and less than about 10 wt %, and the total wt % of the composition does not exceed 100 wt %.

6. The article of claim 1, wherein the composition further comprises a polyol.

7. The article of claim 6, wherein the filler is selected from the group consisting of silica, wollastonite, quartz, alumina, aluminum nitride, boron nitride, silicon nitride, silicon carbide, beryllium oxide, epoxy-silane pretreated silica, epoxy-silane pretreated wollastonite, and combinations thereof.

8. An article, comprising: Heat generating components; and A heat dissipation component is disposed on a surface of the heat generating component, wherein the heat dissipation component comprises a curable composition, wherein the curable composition comprises an epoxy polymerization product of a curable composition, wherein the curable composition comprises: about 20 wt % to about 70 wt % of an aromatic epoxy resin, based on the total wt % of the curable composition; about 30 wt % to about 80 wt % of a filler, based on the total wt % of the curable composition; and More than 0 wt % and less than about 10 wt % of the latent catalytic curing agent, the total wt % of the curable composition does not exceed 100 wt %.

9. The article of claim 8, wherein the heat generating component comprises a component of an electric motor, a component of a generator, a component of an electric drive, a component of a battery, a component of a television, a component of a computer, a component of a medical device, a component of an office machine, or a component of a communication device.

10. The article of claim 8, wherein: The thermal conductivity of the cured composition is about 0.5 W / mK to about 2.0 W / mK; The aromatic epoxy resin is derived from bisphenol A, bisphenol F, tetraepoxypropyl-methylenedianiline, halogenated bisphenol, novolac, o-aminophenol, p-aminophenol, furanone bisphenol, dicyclopentadiene or a combination thereof; or a combination thereof.

11. The article of claim 8, wherein the curable composition is a 1K system.

12. The article of claim 8, wherein: The curable composition further comprises an additive selected from the group consisting of a modifier, a block copolymer comprising functionalized polysilicone, a block copolymer containing polysilicone, a defoamer, an anti-settling agent, an air release agent, a pigment, a UV stabilizer, and combinations thereof; and The amount of the additive in the curable composition is greater than 0 wt % and less than about 10 wt % based on the total wt % of the curable composition.

13. The curable composition of claim 8, wherein the curable composition further comprises a polyol modifier.

14. A method of forming an article, the method comprising: placing a curable composition in a mold, the curable composition comprising an aromatic epoxy resin, a latent catalytic curing agent, and a filler; heating the mold and the curable composition to form a cured composition; and The cured composition is placed on a heat-generating component to form the article.

15. The method of claim 14, wherein heating the mold and the curable composition is performed at a temperature of about 100°C to about 225°C.

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