Epoxy resin composition and method of preparation

Abstract

Embodiments of the present disclosure generally relate to epoxy resin compositions, methods for making epoxy resin compositions, and uses of the epoxy resin compositions. In some embodiments, the compositions include an epoxy resin, a latent catalytic curing agent, and a filler. The compositions can be used in articles. In some embodiments, the articles include a heat-generating component and a composition disposed on the heat-generating component, the composition including an epoxy resin, a latent catalytic curing agent, and a filler.

Description

[Technical Field]

[0001] CROSS-REFERENCE TO RELATED APPLICATIONS

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

[0002] Field TECHNICAL FIELD

[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 technology]

[0003]

[0003] Thermal management of electrical devices, such as electric motors, generators, and automotive components, continues to receive increasing attention as demand for such devices increases. Proper thermal management is critical because the amount of heat that must be dissipated increases as power density increases. Ineffective or inadequate thermal management can lead to reduced performance and lifespan of the device, as overheating can damage materials in or around the electrical device, causing cracks and structural deformation. Safety can also be adversely affected. Therefore, proper thermal management of electrical devices is necessary to improve their reliability, performance, safety, and lifespan.

[0004]

[0004] Several thermal management technologies are known, including resin compositions, heat sinks, thermoelectric coolers, and forced-air systems; however, these technologies have varying degrees of effectiveness. For example, the equipment required for thermoelectric coolers and forced-air systems is bulky, heavy, and expensive. This size and complexity is unacceptable for many applications. Conventional thermal management resin compositions are two-part (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]

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

[0006]

[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 including an aromatic epoxy resin, a latent catalytic curing agent active at a temperature of from 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-dissipating component disposed on a surface of the heat-generating component, the heat-dissipating component comprising a cured composition including an epoxy polymerization product of a curable composition, the curable composition including about 20 wt % to about 70 wt % aromatic epoxy resin, based on the total wt % of the curable composition, about 30 wt % to about 80 wt % filler, based on the total wt % of the curable composition, and greater than 0 wt % and less than about 10 wt % latent catalytic curing agent, wherein the total wt % of the curable composition does not exceed 100 wt %.

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

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

[0011] In another embodiment, there is provided a cured composition comprising the epoxy polymerization product of a curable composition comprising about 20 wt % to about 70 wt % aromatic epoxy resin, based on the total wt % of the curable composition, about 30 wt % to about 80 wt % filler, based on the total wt % of the curable composition, and greater than 0 wt % and less than about 10 wt % latent catalytic curing agent, wherein the total wt % of the curable composition does not exceed 100 wt %, and the cured composition is for coating at least a portion of a heat-generating device, equipment, or 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 to a first temperature, the curable composition including an aromatic epoxy resin, a latent catalytic curing agent, and a filler. The method also includes positioning the heated curable composition in a mold and heating the mold and curable composition at a second temperature to form the cured composition, wherein the first temperature and the second temperature are the same or different. DETAILED DESCRIPTION OF THE INVENTION

[0013]

[0013] 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 for thermal management of various articles, apparatus, devices, or components thereof by removing heat generated by the apparatus, device, or component thereof. "Thermal management" refers to the ability to keep temperature-sensitive elements in or around an electronic / electrical article within a predetermined operating temperature 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 conduct or pass thermal energy or heat to another element or to itself.

[0014] Generally, the compositions can be used with heat-generating components, such as electrical, electronic, or electrical devices, or components thereof. For example, the compositions (or cured compositions) described herein can be in direct or indirect contact with heat-generating components, such as electrical or electronic components. Because the compositions (or cured compositions) are thermally conductive, the compositions (or cured compositions) can remove heat generated by the electrical or electronic components.

[0015] The present inventors have discovered new and improved compositions that are easy to use and have good thermal conductivity. Unlike conventional thermal management compositions, which are typically 2K systems that require on-site mixing, the embodiments described herein can be single-component systems because polymerization does not occur prior to the application of a stimulus such as heat. For example, a composition of the present disclosure can include an epoxy resin, a catalytic curing agent, a filler, and optional additives. Upon application of a stimulus such as heat, the latent catalytic curing agent can, for example, initiate a polyaddition reaction, resulting in coupling, crosslinking, or both of the epoxy resin, among other materials. The composition can be a curable composition that can be stored under ambient conditions. Conventional thermal management compositions lack this capability because they are not single-component systems.

[0016] For example, due to the heat transfer properties of the compositions described herein, the compositions of the present disclosure can be used to remove or dissipate heat from heat-generating elements or components. Such heat-generating elements or components are found, for example, in electrical equipment, electronic equipment, electrical devices, and electronic devices. Accordingly, in some embodiments, an article includes a heat-generating component and a composition of the present disclosure disposed on the heat-generating component. The composition can be disposed on one or more surfaces and can be in direct or indirect contact with one or more surfaces.

[0017]

[0017] Headings are used for convenience only and do not limit the scope of the disclosure. The embodiments described herein may be combined with other embodiments.

[0018] As used herein, a "composition" may include one or more components of the composition, one or more reaction products of two or more components of the composition, the remainder of one or more remaining starting components, or a combination thereof. The compositions of the present disclosure may be prepared by any suitable mixing process.

[0019] composition

[0019] Embodiments of the present disclosure generally relate to compositions that can be used for thermal management of heat-generating devices, equipment, or components thereof. For example, the compositions can be used as casting compositions (reactive compositions), molding compositions (reactive resin compositions), prepregs, among other uses. The compositions can be used in electrical engineering, for example, to coat electrical and electronic components such as capacitors, collectors, and resistors.

[0020] As described herein, the inventors have discovered compositions that have higher thermal conductivity than conventional compositions. In some embodiments, the compositions can be used in the thermal management of various electrical devices and equipment. Here, the compositions can be used to dissipate heat from heat-generating devices, equipment, or components thereof, such as electric motors. As such, the compositions can improve the reliability, performance, safety, and lifespan of the devices and equipment.

[0021] The compositions of the present disclosure may include an epoxy resin, a catalytic curing agent, and a filler. In some embodiments, the compositions may further include one or more additives. The total weight percent (total wt%) of the composition does not exceed 100 wt%. In at least one embodiment, the composition includes an epoxy resin, including an aromatic epoxy resin, a latent catalytic curing agent active at temperatures from about 30°C to about 300°C, and a filler.

[0022] The composition may be a curable composition in which the composition may be cured by application of a stimulus, for example a change in temperature.

[0023]

[0023] 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 selection of epoxy resin is based on, for example, the desired UV resistance.

[0024] Epoxy resins that can be utilized include, for example, epoxy resins prepared from epihalohydrins and phenols or phenol-type compounds, epoxy resins prepared from epihalohydrins and amines, epoxy resins prepared from epihalohydrins and carboxylic acids, or epoxy resins or combinations of epoxy resins prepared from the oxidation of unsaturated compounds.

[0025] Suitable epoxy resins useful in the embodiments described herein include aromatic and non-aromatic epoxy resins. The epoxy resins may contain multiple, and in some embodiments, two, 1,2-epoxy groups per molecule. In some embodiments, the epoxy resins may be liquids rather than solids. In at least one embodiment, the epoxy resins have an epoxide equivalent weight of about 100 to about 5000, e.g., about 100 to about 2000, e.g., about 100 to 500, as determined by the titration method described in ASTM D1652.

[0026] In some embodiments, the epoxy resin may be a non-aromatic hydrogenated cyclohexanedimethanol and diglycidyl ether of hydrogenated bisphenol A type epoxy resin, such as hydrogenated bisphenol A-epichlorohydrin epoxy resin, cyclohexanedimethanol diglycidyl ether, and cycloaliphatic epoxy resin.

[0027] In at least one embodiment, the epoxy resin utilized comprises an aromatic epoxy resin, such as a resin formed from an epihalohydrin and a phenol or a phenol-type compound. Phenolic compounds include compounds having an average of more than one aromatic hydroxyl group per molecule. Examples of phenol-type compounds include dihydroxyphenols, biphenols, bisphenols, halogenated biphenols, halogenated bisphenols, hydrogenated bisphenols, alkylated biphenols, alkylated bisphenols, trisphenols, phenol-aldehyde resins, novolak resins (reaction products of phenol with simple aldehydes such as formaldehyde), halogenated phenol-aldehyde novolak resins, substituted phenol-aldehyde novolak 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.

[0028] In some embodiments, the epoxy resins utilized may include resins made from epihalohydrins and bisphenols, halogenated bisphenols, hydrogenated bisphenols, novolac resins and polyalkylene glycols, or combinations thereof.

[0029] In at least one embodiment, the epoxy resin utilized in the compositions of the present disclosure preferably comprises a resin formed from an epihalohydrin and resorcinol, catechol, hydroquinone, biphenol, bisphenol A, bisphenol AP (1,1-bis(4-hydroxyphenyl)-1-phenylethane), bisphenol F, bisphenol K, tetrabromobisphenol A, phenol-formaldehyde novolac resin, alkyl-substituted phenol-formaldehyde resin, phenol-hydroxybenzaldehyde resin, cresol-hydroxybenzaldehyde resin, dicyclopentadiene-phenol resin, dicyclopentadiene-substituted phenol resin, tetramethylbiphenol, tetramethyltetrabromobiphenol, tetramethyltribromobiphenol, tetrachlorobisphenol A, or a combination thereof.

[0030] In some embodiments, the epoxy resin utilized in the compositions of the present disclosure comprises a resin formed from an epihalohydrin and an amine. Suitable amines include diaminodiphenylmethane, aminophenol, xylylenediamine, aniline, and the like, or combinations thereof.

[0031] In at least one embodiment, the epoxy resin utilized in the compositions of the present disclosure may include a resin formed from an epihalohydrin and a carboxylic acid. 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.

[0032]

[0032] In some embodiments, the epoxy resin compound utilized in the composition of the present disclosure includes a resin produced from an epihalohydrin and a compound having at least one aliphatic hydroxyl group. In such embodiments, it is understood that the resulting resin composition 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 tetrols, and any combination thereof. Also suitable are alkylene oxide adducts of compounds containing at least one aromatic hydroxyl group. In this embodiment, it is understood that the resulting resin composition 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 dihydroxyphenols, 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, hydrocarbon-alkylated phenol resins, or combinations thereof.

[0033] In some embodiments, epoxy resin may refer to a high-grade epoxy resin that is the reaction product of one or more epoxy resin components, as described above, with one or more phenolic compounds, as described above, and / or one or more compounds having an average of more than one aliphatic hydroxyl group per molecule. Alternatively, the epoxy resin may be reacted with a carboxyl-substituted hydrocarbon. Carboxyl-substituted hydrocarbon, as used herein, refers to a hydrocarbon backbone, e.g., C1-C 40 It is described as a compound having a hydrocarbon backbone and one or more carboxyl moieties, for example, a plurality, for example, two carboxyl moieties. 40The hydrocarbon backbone may be a straight-chain or branched alkane or alkene, and optionally contains oxygen. Fatty acids and fatty acid dimers are useful carboxylic acid-substituted hydrocarbons. Fatty acids include caproic acid, caprylic acid, capric acid, octanoic acid, pivalic acid, neodecanoic acid, decanoic acid, lauric acid, myristic acid, palmitic acid, stearic acid, palmitoleic acid, oleic acid, linoleic acid, linolenic acid, erucic acid, pentadecanoic acid, margaric acid, arachidic acid, and their dimers.

[0034] In at least one embodiment, the epoxy resin is the reaction product of a polyepoxide with a compound containing multiple isocyanate moieties or a polyisocyanate. The epoxy resin produced in such a reaction may be an epoxy-terminated polyoxazolidone.

[0035] In some embodiments, the epoxy resin comprises a polymer with cyclohexanol, 4,4'-(1-methylethylidene)bis-, 2-(chloromethyl)oxirane (CAS No. 30583-72-3).

[0036]

[0036] Examples of epoxy resins include dihydroxyphenol epoxy resins, biphenol epoxy resins, bisphenol epoxy resins, halogenated bisphenol epoxy resins, alkylated bisphenol epoxy resins, trisphenol epoxy resins, phenol-aldehyde novolac resin epoxy resins, halogenated phenol-aldehyde novolac resin epoxy resins, alkylated phenol-aldehyde novolac resin epoxy resins, hydrocarbon-phenol resin epoxy resins, hydrocarbon-halogenated phenol resin epoxy resins, hydrocarbon-alkylated phenol resin epoxy resins, or combinations thereof. Illustrative, but non-limiting, examples of epoxy resins include Epikote 1001 epoxy resin (a bisphenol A-based epoxy resin), Epikote 1004 epoxy resin (a bisphenol A-based epoxy resin), Epikote 1007 epoxy resin (a bisphenol A-based epoxy resin), Epikote 1009 epoxy resin (a 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 (a tetrabromobisphenol A-based epoxy resin), Epikote 03243 / LV epoxy resin (an epoxy resin based on (3,4-epoxycyclohexyl)methyl 3,4-epoxycyclohexylcarboxylate and bisphenol A), Epon 164 epoxy resin (epoxidized o-cresol novolac) (all products commercially available from Hexion Inc.).

[0037] In at least one embodiment, the aromatic epoxy resin may be selected from the group consisting of difunctional bisphenol-A-diglycidyl ether, bisphenol-F-diglycidyl ether, tetraglycidylmethylenedianiline, epoxidized tetraphenylethane, derivatives thereof, and combinations thereof. In some embodiments, the aromatic epoxy resin may be derived from bisphenol A, bisphenol F, tetraglycidylmethylenedianiline, halogenated bisphenols, novolacs, ortho-aminophenols, para-aminophenols, fluorenone bisphenols, dicyclopentadiene, or combinations thereof.

[0038]

[0038] Other illustrative but non-limiting examples of epoxy resins include Epikote 828LVEL epoxy resin (a 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 (tetra-glycidyl-methylene-dianiline commercially available from Westlake Epoxy), Epikote 1031 epoxy resin (epoxidized tetra-phenylethane commercially available from Westlake Epoxy).

[0039] In some embodiments, the epoxy resin may be selected to have as high an aromatic content as possible. For example, the epoxy resin may include an aromatic epoxy resin, such as an epoxy resin containing phenol, phenyl, combinations thereof, or other aromatic moieties. The higher the aromatic content, the better the thermal conductivity of the composition.

[0040] In at least one embodiment, the aromatic epoxy resin may have an aromatic content of about 30 wt% to about 70 wt%, e.g., about 40 wt% to about 60 wt%, e.g., about 40 wt% to about 55 wt%, based on the total weight percent of the aromatic epoxy resin. In some embodiments, 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, based on the wt% of the aromatic epoxy resin. Each of the foregoing values ​​may be preceded by the words "about," "at least about," "less than about," or "greater than about," and any of the foregoing values ​​may be used alone to represent an open-ended range or in combination to represent a closed-ended range. Other amounts of epoxy resin are also contemplated.

[0041]

[0041] The aromatic content of an aromatic epoxy resin is calculated by multiplying the molar amount of aromatic structures (C6H4 = 76 g / mol) by the number of aromatic rings in the aromatic epoxy resin and dividing the result by the total molecular weight of the aromatic epoxy resin.

[0042] Combinations or blends of polymers based on epoxide compounds may be utilized in the compositions described herein in any suitable proportions.

[0043] The total amount of one or more epoxy resins in the compositions described herein can be about 20 weight percent (wt%) to about 70 wt%, e.g., about 25 wt% to about 65 wt%, e.g., about 30 wt% to about 60 wt%, e.g., about 35 wt% to about 55 wt%, e.g., about 40 wt% to about 50 wt%, based on the total wt% of the composition. In some embodiments, the total amount (wt%) of one or more epoxy resins in the composition can be 20, 25, 30, 35, 40, 45, 50, 55, 60, 65, or 70, or a range thereof, based on the total wt% of the composition. Each of the foregoing values ​​can be preceded by the words “about,” “at least about,” “less than about,” or “greater than about,” and any of the foregoing values ​​can be used alone to represent an open-ended range or in combination to represent a closed-ended range. Other amounts of epoxy resin are also contemplated.

[0044] The compositions described herein further comprise a catalytic curing agent. The catalytic curing agent can be a latent catalytic curing agent (also referred to as a "latent catalyst"). Latent catalytic curing agents allow for controlled polymerization initiation and simplified operation. For example, the use of latent catalysts can avoid the on-site addition of highly reactive chemicals that can cause mixing problems. Latent catalysts can be stored together without prematurely reacting, thereby allowing for the use of single-component formulations that are ready to polymerize with the application of an appropriate stimulus. Latent catalytic curing agents are activated in response to temperatures above ambient temperature, as further described below.

[0045]

[0045] When a latent catalytic curing agent is described as being "active" at a selected temperature or temperature range, the term "active" refers to the fact that the latent catalytic curing agent causes a reaction (e.g., polyaddition) between one or more components of the composition when the temperature is set at the selected temperature or temperature range.

[0046] A stimulus, such as heat, acts on a material (e.g., a latent catalytic hardener) of the composition. Upon application of the stimulus, the latent catalytic hardener undergoes a polyaddition reaction, resulting in coupling, crosslinking, or both of the epoxy resin, among other materials.

[0047] Conventional heat management compositions typically utilize non-latent catalytic curing agents, for example, that initiate curing at ambient temperatures and can quickly cause an increase in formulation viscosity. As a result, such conventional compositions are made up of 2K systems that require on-site mixing of two or more components. In contrast, the compositions described herein can be single-component systems (1K systems) because polymerization does not occur prior to the application of a stimulus, such as heat. 1K systems already contain all necessary components and are shelf stable. It is also contemplated that the compositions described herein are suitable as storable components of 2K systems or other multi-component systems.

[0048] Suitable latent catalytic curing agents (also referred to as "latent catalysts") include imidazole, substituted imidazole, 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 alkylaluminum complexes), epoxy addition reaction products, tetraphenylene boron complexes, amine borates, metal halides, amine titanates, metal acetylacetonates, metal naphthenates, metal octanoates, other metal salts, metal chelates, or combinations thereof. Latent catalytic curing agents include, for example, boron trichloride dimethyloctylamine complex (CAS No. 347 62-90-8), 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-dimethyl-1-aminoethyl)ether, pentamethyldiethylenetriamine, dimorpholinodiethyl ether, 1,8-diazobicyclo[5.4.0]undec-7-ene (DBU) (CAS number 6674-22-2), N-methylimidazole (also known as 1-methylimidazole (CAS number 616-47-7)), 1,2-dimethylimidazole, triethylenediamine, 1,1,3,3-tetra-methylguanidine, tin(IV) chloride, stannous octoate, or a combination thereof.

[0049] In some examples, the latent catalytic curing agent is an anhydride, an anhydride-free, or a combination thereof. Anhydrides and anhydrides are of concern due to respiratory sensitization effects.

[0050] Suitable latent catalytic curing agents include a sulfonium salt of formula (I), a sulfonium salt of formula (II), a sulfonium salt of formula (III), a sulfonium salt of formula (IV), or a combination thereof: TIFF2026504512000001.tif96170

[0051] In each of formulas (I)-(IV), each R group can be an unsubstituted hydrocarbyl, a substituted hydrocarbyl, or a functional group containing at least one element from Groups 13-17 of the Periodic Table of the Elements. When the R group is a functional group containing at least one element from Groups 13-17, the R group can be selected from halogen (F, Cl, Br, or I), O, N, Se, Te, P, As, Sb, S, B, Si, Ge, Sn, Pb, and the like, for example, C(O)R*, C(C)NR*2, C(O)OR*, NR*2, OR*, SeR*, TeR*, PR*2, AsR*2, SbR*2, SR*, SO x (x=2 or 3), BR*2, SiR*3, GeR*3, SnR*3, PbR*3, etc., where R* can independently be hydrogen or unsubstituted hydrocarbyl, or at least one heteroatom is inserted within the unsubstituted hydrocarbyl.

[0052]

[0052] "Unsubstituted hydrocarbyl" refers to a group consisting solely of hydrogen and carbon atoms. Non-limiting examples of unsubstituted hydrocarbyls include alkyl groups having 1 to 20 carbon atoms, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, iso-butyl, sec-butyl, and tert-butyl, pentyl, hexyl, heptyl, octyl, ethyl-2-hexyl, isooctyl, nonyl, n-decyl, isodecyl, or isomers thereof; alicyclic 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 values ​​can be used alone to create open-ended ranges or in combination to create closed-ended ranges.

[0053] "Substituted hydrocarbyl" refers to an unsubstituted hydrocarbyl in which at least one hydrogen is replaced by 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, etc., e.g., C(O)R*, C(C)NR*2, C(O)OR*, NR*2, OR*, SeR*, TeR*, PR*2, AsR*2, SbR*2, SR*, SO x (x=2 or 3), BR*2, SiR*3, GeR*3, SnR*3, PbR*3, etc.), where R* is independently hydrogen or an unsubstituted hydrocarbyl, or at least one heteroatom is inserted within the unsubstituted hydrocarbyl.

[0054] In each of formulas (I)-(IV), each R group can independently have any suitable number of carbon atoms, such as 1 to 20 carbon atoms, e.g., 1 to 12 carbon atoms, e.g., 1 to 10 carbon atoms, e.g., 1 to 8 carbon atoms, e.g., 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 in formulas (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 foregoing numerical values ​​can be preceded by the words "about," "at least about," "less than about," or "greater than about," and any of the foregoing numerical values ​​can be used alone to designate an open-ended range or in combination to designate a closed-ended range. Each R group in formulas (I)-(IV) may independently be linear or branched, saturated or unsaturated, cyclic or acyclic, aromatic or non-aromatic. With respect to saturation, each R group in formulas (I)-(IV) may independently be fully saturated, partially unsaturated, or fully unsaturated.

[0055] In some embodiments, each R group in formulas (I)-(IV) can independently be C1-C12 alkyl, C3-C8 cycloalkyl, C4-C10 cycloalkylalkyl, or phenyl that is unsubstituted or mono- or polysubstituted with C1-C8 alkyl, C1-C4 alkoxy, halogen, hydroxyl, nitro, phenyl, phenoxy, alkoxycarbonyl having 1 to 4 carbon atoms, or acyl having 1 to 12 carbon atoms.

[0056] In some embodiments, Ar, Ar of formulas (I)-(IV) 1 or Ar 2 Each of Ar, Ar in formulas (I) to (IV) is aromatic. 1 or Ar 2 Each of 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 ring may be independently substituted (mono- or poly-substituted) with one or more R groups as described above.

[0057] In some examples, Ar, Ar in formulas (I)-(IV) 1 or Ar 2 are each independently phenyl, naphthyl, or fluorenyl, and the phenyl, naphthyl, or fluorenyl is unsubstituted or mono- or polysubstituted by C1-C8 alkyl, C1-C4 alkoxy, halogen, hydroxyl, nitro, phenyl, phenoxy, alkoxycarbonyl having 1 to 4 carbon atoms, or acyl having 1 to 12 carbon atoms.

[0058]

[0058] In some embodiments, each arylene of Formulas (I)-(IV) is aromatic. In at least one embodiment, each arylene of Formulas (I)-(IV) is independently monocyclic, polycyclic, or heterocyclic and can be unsubstituted or substituted. In some examples, when substituted, the monocyclic, polycyclic, or heterocyclic ring can be independently substituted (mono- or poly-substituted) with one or more R groups as described above. In some embodiments, each arylene of Formulas (I)-(IV) can independently be phenylene, naphthylene, or fluorenylene, where the phenylene, naphthylene, or fluorenylene is unsubstituted or mono- or poly-substituted with C1-C8 alkyl, C1-C4 alkoxy, halogen, hydroxyl, nitro, phenyl, phenoxy, alkoxycarbonyl having 1 to 4 carbon atoms, or acyl having 1 to 12 carbon atoms.

[0059] In some embodiments, each Q of formulas (I)-(IV) - is a counterion. The counterion is a compound of the formula MX - where M is a metal or metalloid and X is a group containing at least one element from Groups 13-17, such as halogen (F, Cl, Br, or I), O, N, P, S, B, or Si, among others. Illustrative, but non-limiting examples of M include antimony (Sb), silver (Ag), and other metals or metal compounds. Illustrative, but non-limiting examples of X include fluorine (F), hydroxyl (OH), and combinations thereof. - Examples include, but are not limited to, SbF6 - , AsF6 - or SbF5OH - Examples include:

[0060] In formulas (I) and (II), Q - In formulas (III) and (IV), there is only one counter ion, as shown by 2Q - There are two counterions, as shown.

[0061]

[0061] In each of formulas (I) to (IV), when there are multiple R, each R may be the same or different. 1 or Ar 2 When exists, Ar, Ar 1 or Ar 2 In each of formulas (I) to (IV), multiple Q - When exists, each Q - may be the same or different.

[0062] In at least one embodiment, 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 these and other embodiments, each R group of formulas (I)-(IV) is independently C1-C12 alkyl, C3-C8 cycloalkyl, C4-C10 cycloalkylalkyl, or phenyl that is unsubstituted or mono- or polysubstituted with C1-C8 alkyl, C1-C4 alkoxy, halogen, hydroxyl, nitro, phenyl, phenoxy, alkoxycarbonyl having 1 to 4 carbon atoms, or acyl having 1 to 12 carbon atoms; and Ar, Ar of formulas (I)-(IV). 1 , Ar 2or each of their combinations is independently 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, hydroxyl, nitro, phenyl, phenoxy, alkoxycarbonyl having 1 to 4 carbon atoms, or acyl having 1 to 12 carbon atoms; each arylene in formulas (III) and (IV) is independently phenylene, naphthylene, or fluorenylene, wherein the phenylene, naphthylene, or fluorenylene is unsubstituted or mono- or poly-substituted by C1-C8 alkyl, C1-C4 alkoxy, halogen, hydroxyl, nitro, phenyl, phenoxy, alkoxycarbonyl having 1 to 4 carbon atoms, or acyl having 1 to 12 carbon atoms; each Q in formulas (I) to (IV) - are independently SbF6 - , AsF6 - or SbF5OH - is.

[0063]

[0063] Combinations or blends of latent catalytic curing agents may be utilized in the compositions described herein in any suitable proportions.

[0064] The total amount of one or more latent catalytic curing agents in the compositions described herein can be greater than 0 wt %, less than 10 wt %, or a combination thereof, based on the total wt % of the composition, such as from about 0.1 wt % to about 3 wt %, for example from about 0.05 wt % to about 1.5 wt %, for example from about 0.1 wt % to about 1 wt %, for example from about 0.2 wt % to about 0.9 wt %, for example from about 0.3 wt % to about 0.8 wt %, for example from about 0.4 wt % to about 0.7 wt %, for example from about 0.5 wt % to about 0.6 wt %. In some embodiments, the total amount of one or more latent catalytic curing agents in the compositions described herein, based on the total wt% of the composition, 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. Each of the foregoing values ​​can be preceded by the words "about," "at least about," "less than about," or "greater than about," and any of the foregoing values ​​can be used alone to represent an open-ended range or in combination to represent a closed-ended range. Other amounts of one or more latent catalytic curing agents are also contemplated.

[0065] The compositions described herein can further include a filler that is thermally conductive, such as a filler having a thermal conductivity of about 0.5 W / mK or greater (W / mK is watts conducted per degree Kelvin per meter of thickness), a thermal conductivity of about 400 W / mK or less, or a combination thereof. In some embodiments, the filler can be a material having a thermal conductivity of about 0.5 W / mK to about 400 W / mK, e.g., about 1 W / mK to about 100 W / mK, e.g., about 10 W / mK to about 50 W / mK. In some embodiments, the thermal conductivity (W / mK) of the filler can be as low as 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 as high as about 400, 350, 300, 250, 200, 150, 100, 90, 80, 70, 60, 50, 40, 30, 20, or 15. Other thermal conductivities of fillers are also contemplated. Each of the foregoing values ​​can be preceded by the words "about," "at least about," "less than about," or "greater than about," and any of the foregoing values ​​can be used alone to designate an open-ended range, or in combination to designate a closed-ended range. Here, for example, the thermal conductivity of the filler can be greater than about 2 W / mK, less than about 100 W / mK, greater than or equal to about 50 W / mK, less than or equal to about 10 W / mK, from about 0.5 to about 10 W / mK, or from about 30 W / mK to about 50 W / mK.

[0066] 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 may be used. Other fillers are also contemplated. In some embodiments, the application of carbon fillers, such as graphite, is also contemplated if thermal insulation can be ensured.

[0067] In some examples, the filler may include epoxy-silane pretreated materials, such as epoxy-silane pretreated versions of the aforementioned fillers, such as epoxy-silane pretreated silica, epoxy-silane pretreated wollastonite, or combinations thereof. An illustrative, but non-limiting example of an epoxy-silane pretreated silica filler is Millisil W12 EST, available from the Quarzwerke Group. An illustrative, but non-limiting example of an epoxy-silane pretreated wollastonite filler is Tremin 283-100 EST, available from the Quarzwerke Group.

[0068] 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.

[0069] The filler may have a variety of particle sizes. In some embodiments, the filler may have a D50 particle size of about 1 μm to about 100 μm, such as about 35 μm or more, or 15 μm to about 30 μm, or about 1 μm to about 4 μm. In at least one embodiment, the filler's D50 particle size may be in the range of about 35 μm to about 80 μm, such as about 40 μm to about 70 μm, or about 45 μm to about 60 μm. Additionally, or alternatively, the filler's D50 particle size may 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 filler's D50 particle size may 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 diameter) at 50% of the cumulative mass of a particle size distribution. It refers to the particle size at the cumulative 50% point on a cumulative curve where the total mass is 100%. This D50 particle size can be measured by laser diffraction. Laser diffraction can be achieved using ethanol as the solvent and a Marvern Inc. MASTERSIZER 3000 instrument in accordance with ISO standard 13320. Incident laser light is scattered by particles dispersed in the solvent. The intensity and direction of the scattered laser light vary depending on the particle size and are analyzed using Mie theory. From the above analysis, the particle size distribution can be calculated by converting it into the diameter of a sphere with the same volume as the dispersed particles, and the D50 value can be calculated as the median of that distribution to evaluate particle size.

[0070]

[0070] The filler may have any suitable shape. The selection of the filler shape may be based, for example, on, among other things, the heat insulating property, the filling effect, the dispersibility, the viscosity of the resin composition, the thixotropy of the resin composition, the possibility of settling in the composition, the desired heat resistance, the desired thermal conductivity, or a combination thereof. The shape of the filler includes spherical fillers, substantially spherical fillers, non-spherical fillers (e.g., particularly, acicular, plate-like, etc.), or a combination thereof.

[0071]

[0071] Combinations or blends of fillers can be utilized in the compositions described herein in any suitable proportions. Such combinations can include two or more filler types (e.g., silica and epoxysilane-pretreated silica), two or more filler sizes (e.g., silicon carbide having a D50 particle size of about 1.5 μm to about 4 μm and silicon carbide having a D50 particle size of about 20 μm to about 35 μm), two or more shapes (e.g., spherical and acicular), or combinations thereof.

[0072] The total amount of one or more fillers in the compositions described herein can be about 30 wt% to about 80 wt%, e.g., about 30 wt% to about 70 wt%, e.g., about 40 wt% to about 60 wt%, e.g., about 45 wt% to about 55 wt%, based on the total wt% of the composition. Other amounts are contemplated. In some embodiments, the total amount (wt%) of one or more fillers in the composition can be 30, 35, 40, 45, 50, 55, 60, 65, 70, 75, or 80, based on the total wt% of the composition, or a range thereof. Each of the foregoing values ​​can be preceded by the words “about,” “at least about,” “less than about,” or “greater than about,” and any of the foregoing values ​​can be used alone to designate an open-ended range or in combination to designate a closed-ended range.

[0073] The weight ratio of the total amount of epoxy resin to the total amount of filler in the compositions described herein can 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 compositions described herein can 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, or 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 compositions described herein is 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 therein, although other weight ratios are contemplated.

[0074] In addition to the epoxy resin, latent catalytic curing agent, and filler, the compositions described herein may optionally contain 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, antifoaming agents, anti-settling agents, air release agents, pigments, ultraviolet light stabilizers (UV stabilizers), or combinations thereof. Additives may be used for applications such as aiding processing or improving fracture toughness, among others.

[0075] In some embodiments, the total amount of one or more 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 %, based on the total wt % of the composition. Other amounts are also contemplated.

[0076] Suitable modifiers for the compositions include alcohols (also known as monohydric alcohols), polyols (also known as polyhydric alcohols), or combinations thereof. Suitable polyols include, but are not limited to, glycols (dihydric alcohols (diols)) derived from ethylene glycol, such as ethylene glycol, propylene glycol, methyl glycol, trimethylene glycol, neopentyl glycol, diethylene glycol, triethylene glycol, polyethylene glycol, polypropylene glycol, sugar compounds, or compositions thereof. Trihydric or higher alcohols, such as glycerol, trimethylolpropane, glucose, other sugar compounds, or combinations thereof, can also be used. Other alcohols or polyols are also contemplated. In some examples, the compositions described herein include a polyol, such as a glycol, such as ethylene glycol, propylene glycol, polyethylene glycol, polypropylene glycol, glycerol, sugar compounds, or combinations thereof. A non-limiting example of a glycol includes Heloxy PF, a propylene glycol with a weight average molecular weight (Mw) of 400 g / mol. In at least one embodiment, the compositions described herein may include a modifier that is a polyhydric alcohol.

[0077] The total amount of the one or more modifiers in the compositions described herein can be from about 0 wt % to about 10 wt %, e.g., from about 0.05 wt % to about 8 wt %, e.g., 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 the one or more modifiers in the composition 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 wt %, or a range thereof, based on the total wt % of the composition, although other amounts are contemplated. Each of the foregoing numerical values ​​can be preceded by the words "about," "at least about," "less than about," or "greater than about," and any of the foregoing numerical values ​​can be used alone to designate open-ended ranges, or in combination to designate close-ended ranges.

[0078] Suitable block copolymers include functionalized silicones, silicone-containing block copolymers, and combinations thereof. For example, a block copolymer having a silicone and an organic block (the organic block is based on, for example, caprolactone or other lactones), such as Genioperl W35 (Wacker Chemie AG, Munich, Germany), can be used. The block copolymer can function to improve fracture toughness.

[0079]

[0079] Illustrative, but non-limiting, examples of antifoaming agents include FC-402 (comprising tall oil fatty acids, glycols, and Si-containing materials, commercially available from Enterprise Specialty Products); Byk-037 (a volatile-free silicone-containing antifoaming agent commercially available from BYK-Chemie GmbH), Surfynol 104H (a multifunctional surfactant commercially available from Evonik Industries AG), or combinations thereof.

[0080] The total amount of one or more antifoaming agents in the compositions described herein can be from about 0 wt % to about 10 wt %, e.g., from about 0.05 wt % to about 8 wt %, e.g., 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 one or more antifoaming agents in the composition 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 a range thereof, based on the total wt % of the composition, although other amounts are contemplated. Each of the foregoing numerical values ​​can be preceded by the words "about," "at least about," "less than about," or "greater than about," and any of the foregoing numerical values ​​can be used alone to designate open-ended ranges, or in combination to designate close-ended ranges.

[0081] Anti-settling agents can reduce the settling behavior of various components in a composition. Illustrative, but non-limiting, examples of anti-settling agents include Byk 430, Byk 410, Byk 411, and Byk 431, each commercially available from BYK-Chemie GmbH. Combinations of anti-settling agents can also be used. The total amount of one or more anti-settling agents in the compositions described herein can be from about 0 wt % to about 10 wt %, e.g., from about 0.05 wt % to about 8 wt %, e.g., 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 one or more antifoam agents in the composition, based on the total wt% of the composition, 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 a range thereof, although other amounts are contemplated. Each of the foregoing values ​​can be preceded by the words "about," "at least about," "less than about," or "greater than about," and any of the foregoing values ​​can be used alone to designate an open-ended range or in combination to designate a closed-ended range.

[0082] Air release agents can reduce the amount of air bubbles 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 commercially available from BYK-Chemie GmbH. Combinations of anti-settling agents can also be used.

[0083] Illustrative, but non-limiting, examples of pigments 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 available from Chemours), or combinations thereof. Combinations of pigments may also be used. The total amount of one or more pigments in the compositions described herein may be from about 0 wt % to about 10 wt %, for example, from about 0.05 wt % to about 8 wt %, for example, 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 one or more pigments in the composition, based on the total wt % of the composition, 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 a range thereof, although other amounts are contemplated. Each of the foregoing values ​​can be preceded by the words "about," "at least about," "less than about," or "greater than about," and any of the foregoing values ​​can be used alone to designate an open-ended range or in combination to designate a closed-ended range.

[0084] In some embodiments, the compositions described herein may further comprise an additive selected from the group consisting of modifiers, block copolymers comprising functionalized silicones, silicone-containing block copolymers, antifoaming agents, anti-settling agents, air release agents, pigments, ultraviolet light stabilizers (UV stabilizers), and combinations thereof. In these and other embodiments, the amount of 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.

[0085] In at least one embodiment, the compositions described herein comprise about 20 wt% to about 70 wt% aromatic epoxy resin, based on the total wt% of the composition; about 30 wt% to about 80 wt% filler, based on the total wt% of the composition; and greater than 0 wt% and less than 10 wt% latent catalytic curing agent, the total wt% of the composition not exceeding 100 wt%. In some embodiments, the compositions described herein may further comprise a polyhydric alcohol, e.g., a polyhydric alcohol selected from the group consisting of ethylene glycol, propylene glycol, polyethylene glycol, polypropylene glycol, glycerol, sugar compounds, and combinations thereof. In at least one embodiment, the latent catalytic curing agent that may be used with the compositions described herein is a latent catalytic curing agent that is active at temperatures from about 30°C to about 300°C, e.g., from about 50°C to about 275°C.

[0086] As described herein, the compositions are stable under ambient or non-ambient conditions, for example, through the use of latent catalytic curing agents. In contrast, conventional thermal management compositions are typically two-part systems in which the resin and hardener components must be mixed on-site immediately prior to use.

[0087]

[0087] Under ambient conditions (e.g., room temperature (about 20°C to about 25°C)), the compositions described herein can be in the form of a fluid, paste, or viscous material. If the composition is curable, there is no limitation as to the method that can be used to cure the composition.

[0088] method

[0088] Embodiments described herein also generally relate to methods of making or forming the compositions. Conventional heat management compositions are typically made using a two-part system (e.g., a resin component and a hardener component) that is mixed to form the composition. After mixing, the mixture is neatly cast into a preheated mold.

[0089] In contrast, the compositions described herein can be single-component systems. The compositions are heated prior to casting and then poured into a mold for casting. 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.

[0090]

[0090] Generally, the compositions described herein can be made or formed by introducing the ingredients of the composition (epoxy resin, catalytic hardener, filler, and optional additives) to each other and mixing the ingredients.

[0091] The epoxy resin, latent catalytic curing agent, filler, and optional additives may be charged to a vessel and stirred, mixed, or otherwise agitated under mixing conditions effective to form the composition. Mixing conditions may include using mixing pressures of from about 10 mbar (about 1,000 Pa) to about 1,000 mbar (100,000 Pa), for example, from about 20 mbar (about 2,000 Pa) to about 500 mbar (about 50,000 Pa), for example, from about 30 mbar (about 3,000 Pa) to about 150 mbar (about 15,000 Pa), for example, from about 40 mbar (about 4,000 Pa) to about 70 mbar (about 7,000 Pa), for example, about 50 mbar (about 5,000 Pa), although other pressures are contemplated. In some examples, mixing conditions can include mixing pressures of about 1,000, 2,000, 3,000, 4,000, 5,000, 6,000, 7,000, 8,000, 9,000, or 10,000 Pa, or ranges thereof, although other pressures are contemplated. Each of the foregoing numerical values ​​can be preceded by the words "about," "at least about," "less than about," or "greater than about," and any of the foregoing numerical values ​​can be used alone to designate open-ended ranges or in combination to designate closed-ended ranges.

[0092]

[0092] Mixing conditions can include elevated temperatures if necessary, however, if elevated temperatures are used during mixing of the materials, the mixing temperature should be below the temperature at which the latent catalytic curative is activated.

[0093] The mixing conditions may include stirring, mixing, agitating, or a combination thereof, using a suitable device, such as a mechanical stirrer. Such mixing conditions may include the use of a mechanical stirrer (e.g., an overhead stirrer), a magnetic stirrer (e.g., a magnetic stir bar positioned in a vessel above a magnetic stirrer), or other suitable device. For example, a stirrer (having blades or a propeller) may rotate by receiving rotational force from a stirring motor to agitate one or more materials at a suitable rotational speed. The mixing conditions may include the use of a non-reactive gas, such as N2, Ar, or a combination thereof. For example, a non-reactive gas may be introduced into one or more of the epoxy resin, catalytic hardener, filler, and optional additives to degas the various components or otherwise remove unwanted gases (e.g., oxygen) from the mixture.

[0094]

[0094] Mixing conditions, as described above, can include the use of a suitable device, such as a mechanical stirrer, a magnetic stirrer, or other suitable device. For example, a stirrer (having blades or a propeller) can be rotated by receiving rotational force from a stirring motor to stir one or more ingredients at a suitable rotational speed, for example, from 50 revolutions per minute (rpm) to about 1,500 rpm, for example, from about 75 rpm to about 1,000 rpm, for example, from about 100 rpm to about 900 rpm, for example, from about 200 rpm to about 800 rpm, for example, from about 300 rpm to about 700 rpm, for example, from about 400 rpm to about 600 rpm, for example, from about 450 rpm to about 550 rpm, for example, about 500 rpm. Any of the foregoing numerical values ​​can be used alone to represent an open-ended range or in combination to represent a closed-ended range. Other rotational speeds are contemplated and can be selected based on their ability to thoroughly mix the ingredients. Mixing conditions can include mixing for any suitable period of time, e.g., from about 1 minute to about 48 hours, e.g., from about 5 minutes to about 24 hours, e.g., from about 30 minutes to about 10 hours, e.g., from about 1 hour to about 5 hours, e.g., from about 2 hours to about 3 hours, although other periods are contemplated. Any of the foregoing values ​​can be used alone to designate open-ended ranges or in combination to designate closed-ended ranges.

[0095] At this stage, the 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 hardenable composition such that application of a stimulus can harden the composition. The hardenable composition can be in the form of a liquid, a paste, or a gel. One or more of the ingredients of the hardenable composition can be dispersed or suspended as particles.

[0096]

[0096] In some embodiments, the compositions described herein can be curable compositions. The curable compositions can be 1K systems.

[0097] A stimulus such as heat acts on a material (e.g., a latent catalytic hardener) of the composition. Upon application of the stimulus, the latent catalytic hardener initiates a polyaddition reaction, resulting in coupling, crosslinking, or both of the epoxy resin, among other materials, and the composition also hardens.

[0098] The composition may be cured under conditions effective to cure the composition. As noted above, the latent catalytic curing agent present in the composition is activated in response to temperatures above ambient temperature. The selected curing conditions depend, for example, on the temperature at which the latent catalytic curing agent reacts to cause coupling, crosslinking, or both, of the epoxy resin, among other materials. Such curing conditions may include heating the composition to a temperature above ambient temperature, for example, from about 30°C to about 300°C, for example, from about 40°C to about 285°C, for example, from about 50°C to about 275°C, for example, from about 75°C to about 250°C, for example, from about 100°C to about 225°C, for example, from about 125°C to about 200°C, for example, from about 150°C to about 175°C, although other temperatures are contemplated. Any of the foregoing numerical values ​​may be used alone to represent open-ended ranges or in combination to represent closed-ended ranges.

[0099] Curing conditions can include curing for any suitable time, such as from about 1 minute to about 48 hours, such as from about 5 minutes to about 24 hours, such as from about 30 minutes to about 10 hours, such as from about 1 hour to about 5 hours, or from about 2 hours to about 3 hours, although other times are contemplated. Any of the foregoing values ​​can be used alone to represent an open-ended range or in combination to represent a closed-ended range. Curing can be carried out in stages, such as a cure cycle. For example, a cure cycle can include curing the composition at a first temperature for a first time, increasing the temperature to a second temperature at a selected heating rate, and curing the composition at the second temperature for a second time. As a non-limiting example, a cure cycle can have the following profile: curing the composition at about 100°C for about 2 hours, increasing 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 cures or cure cycles are contemplated.

[0100] If necessary, the composition can be introduced into a mold before curing. That is, the curable composition can be formed (e.g., molded) into any suitable shape. Depending on the application for which the composition is to be used, a corresponding mold can be applied to the resulting mixture. Curing can then be carried out at a selected temperature or temperature range, depending on the temperature at which the latent catalytic curing agent used is activated. The cured composition can then be positioned on a heat generating device, heat generating apparatus, or component thereof.

[0101] In some embodiments, the composition may comprise the reaction product of a mixture comprising an epoxy resin, a catalytic curing agent, a filler, and optional additives.

[0102] The compositions of the present disclosure have excellent thermal conductivity. In some embodiments, the compositions have a thermal conductivity that can be about 0.4 W / mK or more, about 5.0 W / mK or less, or a combination thereof. In some examples, the compositions have a thermal conductivity that can be about 0.5 W / mK to about 3.0 W / mK, e.g., about 0.5 W / mK to about 2.0 W / mK, e.g., about 1.0 W / mK to about 1.5 W / mK. In at least one embodiment, the thermal conductivity of the compositions described herein can be at or between 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, although other thermal conductivities are contemplated. Each of the foregoing numerical values ​​can be preceded by the words "about," "at least about," "less than about," or "greater than about," and any of the foregoing numerical values ​​can be used alone to designate open-ended ranges, or in combination to designate close-ended ranges.

[0103] use

[0103] Embodiments of the present disclosure also generally relate to uses of the compositions described herein. The embodiments described herein can be used for thermal management of various apparatuses, devices, and their components. Generally, the compositions can be used with heat-generating components, such as electrical or electronic apparatus, electrical or electronic device, or components thereof. For example, the cured composition (or cured product) can directly or indirectly contact an electrical or electronic component. Because the cured composition is thermally conductive, the cured composition can remove heat generated by the electrical or electronic component. The cured composition can be disposed over, encapsulate, or otherwise cover at least a portion of the apparatus, device, or component thereof.

[0104]

[0104] Illustrative, but non-limiting, examples of heat-generating components (e.g., electrical / electronic equipment and devices) include electric motors, electric generators, electric drive units used in electromobility (e-mobility), or components thereof. E-mobility generally refers to the use of electric powertrain technologies or components thereof used in applications such as electric cars, e-bikes, electric assist bicycles, electric motorcycles, e-buses, e-trucks, among others. Other equipment and devices include batteries, televisions, videos, computers, medical equipment, business machines, or communication devices, or heat-generating devices / apparatus, or components thereof.

[0105]

[0105] Embodiments of the present disclosure also generally relate to articles comprising the compositions described herein. In some embodiments, the article includes 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.

[0106] The heat-generating component can be any suitable component that generates heat or thermal energy. Examples of heat-generating components include electronic devices, electrical devices, electronic equipment, electrical equipment, components thereof, or combinations thereof, as described herein. For example, by contacting a heat-generating component with a thermally conductive composition described herein (either directly or indirectly), the thermally conductive composition can transfer or pass thermal energy or heat from the heat-generating component to another component or to itself. Thus, in some embodiments, the composition can be used to maintain temperature-sensitive components in or around an electronic / electrical article within a predetermined operating temperature to avoid failure. In at least one embodiment, the article comprises a heat-generating component and a composition described herein disposed on the heat-generating component.

[0107] In some embodiments, an article includes a heat-generating component and a heat-dissipating component disposed on (or above) the surface of the heat-generating component. The heat-generating component can be or include a heat-generating element. The heat-dissipating component can be or include a composition described herein. The composition can be a cured composition (or cured product). The heat-dissipating component can be in direct or indirect contact with the heat-generating component. The heat-dissipating component can transfer or pass thermal energy (or heat) from the heat-generating element to another element or to itself. The heat-dissipating component can be used to keep temperature-sensitive elements in or around an electronic / electrical article within a predetermined operating temperature to avoid failure.

[0108]

[0108] In some embodiments, the heat-generating component includes, among others, an electric motor component, a generator component, an electric drive component, a battery component, a television component, a computer component, a medical equipment component, an office machine component, a communication device component, or a combination thereof.

[0109] If desired, the compositions described herein may be used in other applications, such as in the coatings or adhesives industries. The compositions may generally be used to make composites, adhesives, insulation, moldings, binders, paints, sealants, laminates, and other articles or manufactured products.

[0110] In some embodiments, the articles described herein can be made by any suitable method. In at least one embodiment, a method of forming an article includes positioning a curable composition in a mold, the curable composition including an aromatic epoxy resin, a latent catalytic curing agent, and a filler; heating the mold and curable composition to form a cured composition; and positioning the cured composition on a heat-generating component to form the article. In some embodiments, heating the mold and curable composition can be carried out at a temperature of from about 100° C. to about 225° C., although other temperatures are contemplated.

[0111] The following examples are put forward so as to provide those of ordinary skill in the art with a complete disclosure and description of how to make and use 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 with respect to numbers used, but some experimental error and deviation should be accounted for. [Example]

[0112] Test Method

[0112] The thermal conductivity of the compositions was determined according to ASTM E 1461.

[0113] Example Composition Example and comparative compositions were prepared using the components shown in Table 1. The amounts shown in Table 1 are in weight percent unless otherwise specified. The thermal conductivities of the compositions are also shown in Table 1. In Table 1, "C.Ex." indicates comparative examples, and "Ex." indicates examples of the present disclosure. The exemplary compositions are catalytically cured epoxies (using a latent catalytic curing agent). In contrast, the comparative compositions utilize a curing agent as part of a two-part system (resin component and hardener component) that requires on-site mixing.

[0114] 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 tetra-glycidyl-methylene-dianiline epoxy resin, and Epikote 1031 is an epoxidized tetra-phenylethane epoxy resin, all of which are commercially available from Westlake Epoxy. Epikote 828LVEL, Epikote 162, Epikote 158, Epikote 496, and Epikote 1031 are used as epoxy resins.

[0115] Polypropylene glycol (400 g / mol), commercially available from Hexion Inc. under the trade name Heloxy, was used as the modifier. Boron trichloride dimethyloctylamine complex and 1-methylimidazole (both commercially available from Hexion Inc.) were used as catalysts. Fillers included Millisil W12 EST, commercially available from Quarzwerke Group, Tremin 283-100 EST, also commercially available from Quarzwerke Group, and SiC, commercially available from ESD-SIC.

[0116] Comparative examples include curing components such as methyl nadic anhydride (also known as methyl-5-norbornene-2,3-dicarboxylic anhydride; CAS No. 25134-21-8) available from Polynt; DBU (1,8-diazabicyclo[5.4.0]undec-7-ene; CAS No. 6674-22-2) available from BASF; an additive that is an air release agent (polysiloxane) and an anti-settling agent (urea-modified, medium-polarity polyamide); and Genioperl W35 (modifier) ​​available from Wacker Chemie.

[0117]

[0117] Exemplary compositions were made according to the following non-limiting procedure. Before blending the materials, the resin and filler were individually heated to a temperature of about 70°C for about 2 hours. After removing the heat (to prevent the latent catalytic curing agent from reacting), the resin, filler, and latent catalytic curing agent were charged into a container and mixed at about 500 revolutions per minute (rpm) to about 1,000 rpm and a pressure of about 50 mbar (about 5,000 Pa). The compositions were placed into individual molds, and the compositions were cured in the molds using a time and temperature profile that resulted in either a full cure or sufficient cure to release the cured composition from the mold after the cure cycle. In these examples, the following cure profile was used: hold at about 100°C for about 2 hours, ramp to about 190°C, cure at about 190°C for about 3 hours. The cured compositions were then cooled to room temperature. The cured compositions were then removed from the molds. TIFF2026504512000002.tif249170TIFF2026504512000003.tif41170

[0118] The thermal conductivity data in Table 1 show that the example compositions have thermal conductivities that are about 10% to about 15% higher than the comparative compositions. For example, Comparative Example 1, which contains EP828LVEL and wollastonite filler, has a thermal conductivity of about 0.54 W / mK, while Example 1, which contains about 25% EP162, about 75% EP158, and the same amount of wollastonite filler, has a higher thermal conductivity of about 0.61 W / mK. Although Examples 2, 3, and Comparative Example 2 contain the same Millisil filler (about 72%), the thermal conductivities of Example 2a (about 0.96 W / mK) and Example 2b (about 1.02 W / mK) are significantly improved over Comparative Example 2 (0.84 W / mK). Similarly, Example 3 and Comparative Example 3 contain the same Millisil filler (approximately 69%), yet the thermal conductivity of Example 3 (approximately 0.91 W / mK) is significantly improved over Comparative Example 3 (0.8 W / mK). Furthermore, Example 4 and Comparative Example 4 contain the same silicon carbide filler, yet Example 4 (approximately 0.57 W / mK) exhibits improved thermal conductivity over Comparative Example 4 (0.51 W / mK). While not wishing to be bound by theory, it is believed that the high aromatic content of the exemplary compositions contributes to the significant improvement in thermal conductivity. For example, each of the comparative examples is diluted with a curable component, whereas the exemplary compositions of the present disclosure are not diluted with a curable component. This lack of dilution results in the relatively higher aromatic content of the example compositions compared to the comparative examples. Additionally, unlike the comparative examples, which contain an anhydride curing agent (methyl nadic anhydride), the examples of the present disclosure do not contain an anhydride. Anhydrides are a concern due to their respiratory sensitization effects.

[0119] The thermal conductivity data also indicate that the compositions of the present disclosure can be utilized in the thermal management of heat-generating elements, for example, to transfer or pass thermal energy or heat from the heat-generating element to another element or to itself. For example, the compositions of the present disclosure can be utilized with heat-generating devices, heat-generating apparatus, components thereof, or combinations thereof. By contacting (directly or indirectly) the compositions described herein with the heat-generating device, heat-generating apparatus, or components thereof, the compositions can be utilized to maintain temperature-sensitive elements within a predetermined operating temperature to avoid failure.

[0120]

[0120] Examples also show that the compositions described herein can be single-component systems (1K systems) because polymerization does not occur prior to the application of a stimulus, such as heat (e.g., a cure profile). The compositions of the present disclosure can also be stored at ambient temperature. In contrast, comparative compositions for thermal management are 2K systems that require on-site mixing.

[0121] Unlike conventional thermal management compositions, which are typically 2K systems requiring on-site mixing, the embodiments described herein can be single-component systems because polymerization does not occur prior to the application of a stimulus such as heat. For example, a composition of the present disclosure can include an epoxy resin, a catalytic curing agent, a filler, and optional additives. Upon application of a stimulus such as heat, the latent catalytic curing agent can, for example, cause a polyaddition reaction, resulting in coupling, crosslinking, or both of the epoxy resin, among other materials. The composition can be a curable composition that can be stored under ambient conditions. Conventional thermal management compositions lack this capability because they are not single-component systems.

[0122]

[0122] It should be noted that, compared to the prior art, the efficiency of state-of-the-art electrical and electronic devices can be significantly improved by using the thermally conductive compositions described herein. This is because the compositions of the present disclosure exhibit improved thermal conductivity (i.e., improved heat dissipation from heat-generating components), which in turn allows for lower operating temperatures for such electrical and electronic devices. As a result, the reduced operating temperatures enabled by the compositions of the present disclosure allow for increased power output compared to conventional heat dissipation technologies.

[0123] Overall, the thermal conductivity data for the exemplary compositions demonstrate that, compared to conventional compositions, the compositions of the present disclosure can provide lower operating temperatures when used with electrical devices. This beneficial reduction in operating temperature translates to reduced electrical losses from the electrical device and reduced thermal degradation of the electrical device. This is particularly true for electric drivetrains used in electromobility (e-mobility), which typically operate at the highest temperatures of all e-mobility devices. As noted above, e-mobility generally refers to the use of electric powertrain technology, particularly in applications such as electric cars, e-bikes, electric assist bicycles, electric motorcycles, e-buses, and e-trucks. Additionally, the compositions described herein may be free of acid anhydrides as curing agents, which present concerns about respiratory sensitization.

[0124]

[0124] 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 to dissipate heat from heat-generating devices, heat-generating equipment, or components thereof, such as electrical and electronic devices, electrical and electronic equipment, or components thereof. The compositions can be curable compositions that can be stored under ambient conditions.

[0125]

[0125] Reference herein to an R group, alkyl, substituted alkyl, hydrocarbyl, or substituted hydrocarbyl, without specifying a particular isomer (such as butyl), expressly discloses all isomers (such as n-butyl, iso-butyl, sec-butyl, and tert-butyl). For example, reference to an R group having four carbon atoms expressly discloses all isomers thereof. When a compound is described herein such that a specific isomer, enantiomer, or diastereomer of the compound is not specified, for example, in the formula or chemical name, the description is intended to include each isomer and enantiomer of the described compound, alone or in any combination.

[0126] As is apparent from the summary and specific embodiments set forth above, while aspects of the embodiments have been illustrated and described, various modifications can be made without departing from the spirit and scope of the present disclosure. Accordingly, no limitation of the present disclosure is intended. Similarly, the term "comprising" is considered synonymous with the word "including." Similarly, whenever the transitional phrase "comprising" appears before a composition, element, group of elements, or method, it is understood that the same composition, method, or group of elements also has the transitional phrase "consisting essentially of," "consisting of," "selected from the group of consisting of," or "is" preceding the recitation of the composition, element, elements, or method, and vice versa; for example, it is understood that the terms "comprising," "consisting essentially of," and "consisting of" also include the product of a combination of the elements listed after the term.

[0127] For purposes of this disclosure, unless otherwise expressly stated, all numerical values ​​in the detailed description and claims herein are modified by "about" or "approximately" the stated value, taking into account experimental error and variations that would be expected by one of ordinary skill in the art. For brevity, only certain ranges are explicitly disclosed herein. However, ranges from any lower limit may be combined with any upper limit to create ranges not expressly recited. Similarly, ranges from any lower limit may be combined with any other lower limit to create ranges not expressly recited, and similarly, ranges from any upper limit may be combined with any other upper limit to create ranges not expressly recited. For example, reciting a numerical range of 1 to 5 includes subranges such as 1 to 4, 1.5 to 4.5, 1 to 2, etc. As another example, reciting a numerical range of 1 to 5, e.g., 2 to 4, includes subranges such as 1 to 4 and 2 to 5. Furthermore, ranges include all points or individual values ​​between their endpoints, even if not expressly recited. For example, reciting a numerical range of 1 to 5 includes the numbers 1, 1.5, 2.75, 3, 3.80, 4, 5, etc. Thus, every point or individual value acts as its own lower or upper limit and may be combined with other points or individual values, or other lower or upper limits, to describe ranges not expressly recited.

[0128]

[0128] As used herein, the indefinite article "a" or "an" shall mean "at least one" unless expressly stated to the contrary or the context clearly indicates otherwise. For example, an embodiment including a "filler" includes embodiments including one, two, or more fillers, unless expressly stated to the contrary or the context clearly indicates that only one filler is included.

[0129]

[0129] While the foregoing is directed to aspects of the present 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. A heat-generating member; A composition disposed on a heat-generating component, aromatic epoxy resin, a latent catalytic curing agent that is active at a temperature of from about 30° C. to about 300° C.; and Filler a composition comprising: Including, goods.

2. the aromatic epoxy resin has an aromatic content of about 30 wt % to about 70 wt %, based on the total weight percent of the aromatic epoxy resin; The aromatic epoxy resin is selected from the group consisting of difunctional bisphenol-A-diglycidyl-ether, bisphenol-F-diglycidyl-ether, tetra-glycidyl-methylene-dianiline, epoxidized tetra-phenylethane, derivatives thereof, and combinations thereof; or combinations of these 2. The article of claim 1.

3. 10. The article of claim 1, wherein the latent catalytic curing agent is selected from the group consisting of imidazoles, substituted imidazoles, imidazole adducts, imidazole complexes, tertiary amines, oligomeric polyethylene piperazines, quaternary ammonium compounds, quaternary phosphonium compounds, urea derivatives, boron trifluoride complexes, boron trichloride complexes, epoxy addition reaction products, tetraphenylene boron complexes, amine borates, amine titanates, metal acetylacetonates, metal naphthenates, metal octoates, other metal salts, metal chelates, and combinations thereof.

4. 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 formulas (I) to (IV), each R group is independently C1-C12 alkyl, C3-C8 cycloalkyl, C4-C10 cycloalkylalkyl, or phenyl that is unsubstituted or mono- or polysubstituted with C1-C8 alkyl, C1-C4 alkoxy, halogen, hydroxyl, 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 is independently phenyl, naphthyl, or fluorenyl, wherein the phenyl, naphthyl, or fluorenyl is unsubstituted or mono- or polysubstituted by C1-C8 alkyl, C1-C4 alkoxy, halogen, hydroxyl, nitro, phenyl, phenoxy, alkoxycarbonyl having 1 to 4 carbon atoms, or acyl having 1 to 12 carbon atoms; each arylene is independently phenylene, naphthylene, fluorenylene, wherein the phenylene, naphthylene, or fluorenylene is unsubstituted or mono- or polysubstituted with C1-C8 alkyl, C1-C4 alkoxy, halogen, hydroxyl, nitro, phenyl, phenoxy, alkoxycarbonyl having 1 to 4 carbon atoms, or acyl having 1 to 12 carbon atoms; Each Q － are independently SbF ６ － , AsF ６ － or SbF ５ OH － That is, The article of claim 1.

5. The composition comprises: about 20 wt % to about 70 wt % of an aromatic epoxy resin, based on the total wt % of the composition; about 30 wt % to about 80 wt % filler, based on the total wt % of the composition; greater than 0 wt % and less than about 10 wt % of a latent catalytic curing agent; 10. The article of claim 1, comprising:

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

7. 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. a heat-generating component; a heat-dissipating component disposed over a surface of a heat-generating component, the heat-dissipating component comprising a cured composition comprising an epoxy polymerization product of a curable composition, the curable composition comprising: about 20 wt % to about 70 wt % aromatic epoxy resin, based on the total wt % of the curable composition; about 30 wt % to about 80 wt % filler, based on the total wt % of the hardenable composition; and greater than 0 wt% and less than about 10 wt% of a latent catalytic curing agent wherein the total wt% of the curable composition does not exceed 100 wt%; and Including, goods.

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

10. the cured composition has a thermal conductivity of about 0.5 W / mK to about 2.0 W / mK; The aromatic epoxy resin is derived from bisphenol A, bisphenol F, tetraglycidyl-methylenedianiline, halogenated bisphenol, novolac, ortho-aminophenol, para-aminophenol, fluorenone bisphenol, dicyclopentadiene or a combination thereof; or a combination thereof, 9. The article of claim 8.

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

12. the curable composition comprises an additive selected from the group consisting of a modifier, a block copolymer comprising a functionalized silicone, a silicone-containing block copolymer, an antifoaming agent, an anti-settling agent, an air release agent, a pigment, an ultraviolet light stabilizer, and combinations thereof; and the amount of 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; 9. The article of claim 8.

13. The cured composition of claim 8 , wherein the curable composition further comprises a polyhydric alcohol modifier.

14. 1. A method of forming an article, comprising: positioning 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; positioning the cured composition on a heat-generating component to form an article; A method comprising:

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

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